addenda and errata
e4
Odabas¸og˘luet al. C22H30ClO4PS doi:10.1107/S1600536805027789 Acta Cryst.(2005). E61, e4–e5
Acta Crystallographica Section E Structure Reports
Online
ISSN 1600-5368
O
,
O
-Bis(2-
tert
-butyl-4-methoxyphenyl)
chlorothiophosphonate. Corrigendum.
Mustafa Odabas¸og˘lu,a* Orhan Bu¨yu¨kgu¨ngo¨rb and
C¸ig˘dem Albayraka
aDepartment of Chemistry, Ondokuz Mayıs
University, TR-55139 Samsun, Turkey, and
bDepartment of Physics, Ondokuz Mayıs
University, TR-55139 Samsun, Turkey
Correspondence e-mail: [email protected]
Key indicators
Single-crystal X-ray study
T= 150 K
Mean(C–C) = 0.002 A˚ Disorder in main residue
Rfactor = 0.028
wRfactor = 0.073
Data-to-parameter ratio = 12.1
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2005 International Union of Crystallography Printed in Great Britain – all rights reserved
In the original report by Odabas¸og˘lu, Bu¨yu¨kgu¨ngo¨r & Albayrak [Acta Cryst. (2005), E61, o2528–o2530], the structure was reported in the incorrect space group Cc. The structure is now reported as disordered in the correct space group C2/c. The P atom lies on a twofold rotation axis.A revised description of the hydrogen bonding is also given.
Comment
An ORTEP-3 (Farrugia, 1997) view of (I) and a packing diagram are shown in Figs. 1 and 2, respectively. The P atom lies on a twofold rotation axis, eading to disorder of the Cl and S atoms. Compound (I) has no classical hydrogen bonds, but there are two C—H interactions: H8A Cg1= 3.12 (2) A˚ and C8—H8A Cg1 = 122.8 (2)(Cg1 is the centroid of the C1ii–C6ii ring), and H11A Cg2 = 2.71 (2) A˚ and C11— H11A Cg2 = 142.7 (1)(Cg2 is the centroid of the C1iii
–C6iii
[image:1.610.206.461.379.483.2]Received 8 August 2005 Accepted 5 September 2005 Online 17 September 2005
Figure 2
[image:1.610.206.460.520.724.2]A view of the packing of (I); C—H interactions are drawn as dashed lines.
Figure 1
A view of (I), with the atom-numbering scheme and 50% probability displacement ellipsoids[Symmetry code: (i)x+ 1,y,z+1
ring) [symmetry codes: (ii)x, 1y,1 2+z; (iii)
1 2x,
1
2y,z]. The dihedral angle between the symmetry-related benzene rings is 41.2 (2). Selected bond distances and angles are given in Table 1.
Experimental
Crystal data
C22H30ClO4PS Mr= 456.94 Monoclinic,C2=c a= 23.592 (3) A˚
b= 8.3111 (6) A˚
c= 12.5067 (14) A˚
= 105.740 (9)
V= 2360.3 (4) A˚3 Z= 4
Dx= 1.286 Mg m
3
MoKradiation
Cell parameters from 16485 reflections
= 1.7–26.7
= 0.34 mm1 T= 150 K Prism, colorless 0.640.590.55 mm
Data collection
Stoe IPDS-II diffractometer
!scans
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)
Tmin= 0.824,Tmax= 0.869
16485 measured reflections 2327 independent reflections
2146 reflections withI> 2(I)
Rint= 0.032 max= 26.0
h=28!28
k=10!10
l=15!15
Refinement
Refinement onF2 R[F2> 2(F2)] = 0.028 wR(F2) = 0.073
S= 1.08 2327 reflections 192 parameters
All H-atom parameters refined
w= 1/[2
(Fo2) + (0.0362P)2
+ 1.6163P]
whereP= (Fo2+ 2Fc2)/3
(/)max= 0.002
max= 0.17 e A˚
3
min=0.34 e A˚
3
Table 1
Selected geometric parameters (A˚ ,).
C1—C2 1.3946 (18)
C1—C6 1.4086 (17)
C1—O1 1.4226 (14)
C2—C3 1.3860 (18)
C3—C4 1.3979 (18)
C4—C5 1.4017 (19)
C5—C6 1.4088 (18)
O1—P1 1.5750 (9)
P1—S1i
1.9791 (4)
P1—Cl1 1.9791 (4)
C2—C1—C6 123.25 (11)
C2—C1—O1 119.13 (11)
C6—C1—O1 117.58 (11)
C3—C2—C1 119.77 (12)
C2—C3—C4 119.11 (12)
C3—C4—C5 120.39 (11)
C4—C5—C6 121.99 (12)
C1—C6—C5 115.48 (11)
O1—P1—O1i
97.08 (7) O1—P1—S1i
111.27 (4)
O1—P1—Cl1 111.44 (3)
S1i—P1—Cl1 113.26 (3)
Symmetry code: (i)xþ1;y;zþ1 2.
All H atoms were refined freely. Atoms S1 and Cl1 were assigned to the same atomic site and refined freely with the same atomic coordinates and with fixed site-occupancy factors of 0.5.
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement:
X-AREA; data reduction:X-RED32(Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97(Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics:ORTEP-3for Windows (Farrugia, 1997); software used to prepare material for publication:WinGX(Farrugia, 1999).
References
Farrugia, L. J. (1997).J. Appl. Cryst.30, 565. Farrugia, L. J. (1999).J. Appl. Cryst.32, 837–838.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Go¨ttingen, Germany.
Stoe & Cie (2002).X-AREA(Version 1.18) andX-RED32(Version 1.04). Stoe & Cie, Darmstadt, Germany.
addenda and errata
Acta Cryst.(2005). E61, e4–e5 Odabas¸og˘luet al. C
supporting information
sup-1
Acta Cryst. (2005). E61, e4–e5supporting information
Acta Cryst. (2005). E61, e4–e5 [doi:10.1107/S1600536805027789]
O,O-Bis(2-tert-butyl-4-methoxyphenyl) chlorothiophosphonate. Corrigendum.
Mustafa Odaba
ş
o
ğ
lu, Orhan B
ü
y
ü
kg
ü
ng
ö
r and
Ç
i
ğ
dem Albayrak
S1. Comment
An ORTEP-3 (Farrugia, 1997) view of (I) and a packing diagram are shown in Figs. 1 and 2, respectively. Compound (I)
has no classical hydrogen bonds but there are two C—H···π interactions: H8A···Cg1= 3.12 (2) Å and C8—H8A···Cg1 =
122.8 (2)° [Cg1 is the centroid of the C1i–C6i ring; and H11A···Cg2 = 2.71 (2) Å and C11—H11A···Cg2 = 142.7 (1)°
(Cg2 is the centroid of the C1ii–C6ii ring); symmetry codes: (i) x, 1 − y, 1/2 + z; (ii) 1/2 − x, 1/2 − y, − z]. The dihedral
angle between the symmetry-related benzene rings in (I) is 41.2 (2)°. Selected bond distances and angles for (I) are given
in Table 1. The benzene ring is planar, with a maximum deviation from the plane defined by the six ring atoms of
0.007 (1) Å (for C3).
S2. Experimental
Compound (I) was prepared by the method of Odabaşoǧlu et al. (2005), using 2-tert-butyl-4-methoxyphenol and PSCl3 as
starting materials. Crystals of (I) suitable for single-crystal X-ray diffraction were grown by slow evaporation of a
solution in n-hexane (yield 77%, m.p. 423 K). Analysis calculated: C 57.83, H 6.57%; found: C 57.36, H 6.38%.
S3. Refinement
All H atoms were refined freely. Atoms S1 and Cl1 were assigned to the same atomic site and refined freely with the
[image:3.610.119.486.468.617.2]same atomic coordinates and with fixed site-occupancy factors of 0.5.
Figure 1
A view of (I), with the atom-numbering scheme and 50% probability displacement ellipsoids·[Symmetry codes: (i) −x, y,
supporting information
[image:4.610.126.487.70.363.2]sup-2
Acta Cryst. (2005). E61, e4–e5Figure 2
A view of the packing of (I); C—H···π interactions are drawn as dashed lines.
O,O-Bis(2-tert-butyl-4-methoxyphenyl) chlorothiophosphonate
Crystal data
C22H30ClO4PS Mr = 456.94
Monoclinic, C2/c Hall symbol: -C 2yc a = 23.592 (3) Å b = 8.3111 (6) Å c = 12.5067 (14) Å β = 105.740 (9)° V = 2360.3 (4) Å3 Z = 4
F(000) = 968 Dx = 1.286 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 16485 reflections θ = 1.7–26.7°
µ = 0.34 mm−1 T = 150 K Prism, colorless 0.64 × 0.59 × 0.55 mm
Data collection
Stoe IPDS-II diffractometer
Graphite monochromator ω scans
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) Tmin = 0.824, Tmax = 0.869 16485 measured reflections
2327 independent reflections 2146 reflections with I > 2σ(I) Rint = 0.032
θmax = 26.0°, θmin = 1.8° h = −28→28
supporting information
sup-3
Acta Cryst. (2005). E61, e4–e5Refinement
Refinement on F2 Least-squares matrix: full R[F2 > 2σ(F2)] = 0.028 wR(F2) = 0.073 S = 1.08 2327 reflections 192 parameters 0 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: difference Fourier map All H-atom parameters refined
w = 1/[σ2(F
o2) + (0.0362P)2 + 1.6163P] where P = (Fo2 + 2Fc2)/3
(Δ/σ)max = 0.002 Δρmax = 0.17 e Å−3 Δρmin = −0.34 e Å−3
Special details
Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x y z Uiso*/Ueq Occ. (<1)
C1 0.58872 (5) 0.29212 (15) 0.41994 (10) 0.0224 (3) C2 0.59796 (6) 0.14466 (16) 0.47516 (11) 0.0258 (3) C3 0.65010 (6) 0.11722 (16) 0.55649 (11) 0.0272 (3) C4 0.69210 (5) 0.23993 (16) 0.58337 (10) 0.0249 (3) C5 0.68201 (6) 0.38769 (16) 0.52737 (11) 0.0252 (3) C6 0.62988 (5) 0.41888 (15) 0.44326 (10) 0.0233 (3) C7 0.61903 (6) 0.58369 (16) 0.38318 (12) 0.0296 (3) C8 0.61032 (8) 0.56105 (19) 0.25687 (13) 0.0374 (3) C9 0.56458 (8) 0.66639 (19) 0.40646 (15) 0.0402 (4) C10 0.67218 (8) 0.6983 (2) 0.42394 (16) 0.0453 (4) C11 0.78481 (6) 0.32952 (19) 0.70159 (13) 0.0343 (3) O1 0.53449 (4) 0.31975 (10) 0.33826 (7) 0.0257 (2) O2 0.74184 (4) 0.20383 (12) 0.66690 (8) 0.0319 (2)
P1 0.5000 0.19428 (5) 0.2500 0.02610 (13)
Cl1 0.554354 (14) 0.06331 (4) 0.18992 (3) 0.03162 (11) 0.50 S1 0.554354 (14) 0.06331 (4) 0.18992 (3) 0.03162 (11) 0.50 H2 0.5683 (7) 0.0634 (19) 0.4571 (13) 0.032 (4)*
supporting information
sup-4
Acta Cryst. (2005). E61, e4–e5H10A 0.7097 (9) 0.650 (2) 0.4105 (16) 0.056 (6)* H10B 0.6816 (9) 0.720 (2) 0.5075 (19) 0.059 (6)* H10C 0.6631 (9) 0.798 (2) 0.3852 (17) 0.056 (5)* H11A 0.8030 (8) 0.360 (2) 0.6410 (15) 0.042 (5)* H11B 0.8151 (8) 0.282 (2) 0.7644 (15) 0.041 (4)* H11C 0.7671 (7) 0.427 (2) 0.7281 (14) 0.035 (4)*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
C1 0.0207 (6) 0.0240 (6) 0.0204 (6) 0.0000 (5) 0.0020 (4) −0.0009 (5) C2 0.0254 (6) 0.0247 (6) 0.0254 (6) −0.0045 (5) 0.0037 (5) 0.0004 (5) C3 0.0293 (7) 0.0261 (7) 0.0243 (6) −0.0001 (5) 0.0037 (5) 0.0030 (5) C4 0.0223 (6) 0.0311 (7) 0.0198 (6) 0.0006 (5) 0.0029 (5) −0.0023 (5) C5 0.0241 (6) 0.0262 (6) 0.0246 (6) −0.0044 (5) 0.0053 (5) −0.0041 (5) C6 0.0253 (6) 0.0223 (6) 0.0222 (6) −0.0015 (5) 0.0064 (5) −0.0023 (5) C7 0.0315 (7) 0.0212 (6) 0.0333 (7) −0.0037 (5) 0.0041 (6) 0.0019 (5) C8 0.0447 (9) 0.0336 (8) 0.0327 (8) −0.0051 (7) 0.0086 (7) 0.0086 (6) C9 0.0443 (9) 0.0242 (7) 0.0498 (10) 0.0051 (6) 0.0087 (7) −0.0019 (7) C10 0.0439 (9) 0.0279 (8) 0.0556 (11) −0.0124 (7) −0.0012 (8) 0.0062 (7) C11 0.0253 (7) 0.0395 (8) 0.0322 (7) −0.0019 (6) −0.0021 (6) −0.0082 (6) O1 0.0238 (4) 0.0220 (4) 0.0260 (5) 0.0002 (3) −0.0022 (4) −0.0019 (4) O2 0.0252 (5) 0.0360 (5) 0.0283 (5) −0.0015 (4) −0.0033 (4) 0.0005 (4) P1 0.0288 (2) 0.0192 (2) 0.0242 (2) 0.000 −0.00339 (18) 0.000
Cl1 0.02605 (18) 0.0368 (2) 0.0320 (2) 0.00652 (13) 0.00781 (14) −0.00242 (13) S1 0.02605 (18) 0.0368 (2) 0.0320 (2) 0.00652 (13) 0.00781 (14) −0.00242 (13)
Geometric parameters (Å, º)
C1—C2 1.3946 (18) C8—H8C 1.00 (2)
C1—C6 1.4086 (17) C9—H9A 1.00 (2)
C1—O1 1.4226 (14) C9—H9B 1.02 (2)
C2—C3 1.3860 (18) C9—H9C 0.994 (19)
C2—H2 0.955 (16) C10—H10A 1.03 (2)
C3—C4 1.3979 (18) C10—H10B 1.02 (2)
C3—H3 0.974 (17) C10—H10C 0.96 (2)
C4—O2 1.3759 (15) C11—O2 1.4383 (17)
C4—C5 1.4017 (19) C11—H11A 0.998 (18)
C5—C6 1.4088 (18) C11—H11B 0.990 (18)
C5—H5 0.952 (16) C11—H11C 1.009 (17)
C6—C7 1.5499 (18) O1—P1 1.5750 (9)
C7—C10 1.5468 (19) P1—O1i 1.5750 (9)
C7—C8 1.548 (2) P1—S1i 1.9791 (4)
C7—C9 1.552 (2) P1—Cl1i 1.9791 (4)
C8—H8A 1.00 (2) P1—Cl1 1.9791 (4)
C8—H8B 0.948 (19)
supporting information
sup-5
Acta Cryst. (2005). E61, e4–e5C2—C1—O1 119.13 (11) C7—C9—H9B 111.8 (11)
C6—C1—O1 117.58 (11) H9A—C9—H9B 108.6 (16)
C3—C2—C1 119.77 (12) C7—C9—H9C 112.5 (11)
C3—C2—H2 120.3 (9) H9A—C9—H9C 107.2 (15)
C1—C2—H2 119.9 (9) H9B—C9—H9C 106.6 (15)
C2—C3—C4 119.11 (12) C7—C10—H10A 111.4 (11)
C2—C3—H3 121.1 (9) C7—C10—H10B 112.1 (11)
C4—C3—H3 119.8 (9) H10A—C10—H10B 106.1 (16)
O2—C4—C3 115.24 (12) C7—C10—H10C 108.5 (12)
O2—C4—C5 124.38 (11) H10A—C10—H10C 109.9 (16)
C3—C4—C5 120.39 (11) H10B—C10—H10C 108.8 (16)
C4—C5—C6 121.99 (12) O2—C11—H11A 111.5 (10)
C4—C5—H5 117.3 (9) O2—C11—H11B 104.1 (10)
C6—C5—H5 120.7 (9) H11A—C11—H11B 109.7 (14)
C1—C6—C5 115.48 (11) O2—C11—H11C 111.3 (9)
C1—C6—C7 123.14 (11) H11A—C11—H11C 110.4 (14)
C5—C6—C7 121.37 (11) H11B—C11—H11C 109.7 (13)
C10—C7—C8 106.40 (13) C1—O1—P1 126.11 (8)
C10—C7—C6 111.83 (11) C4—O2—C11 117.18 (11)
C8—C7—C6 110.24 (11) O1—P1—O1i 97.08 (7)
C10—C7—C9 107.68 (13) O1—P1—S1i 111.27 (4)
C8—C7—C9 110.96 (12) O1i—P1—S1i 111.44 (3)
C6—C7—C9 109.67 (12) O1—P1—Cl1i 111.27 (4)
C7—C8—H8A 109.7 (11) O1i—P1—Cl1i 111.44 (3)
C7—C8—H8B 112.2 (11) S1i—P1—Cl1i 0.00 (2)
H8A—C8—H8B 108.9 (16) O1—P1—Cl1 111.44 (3)
C7—C8—H8C 110.0 (12) O1i—P1—Cl1 111.27 (4)
H8A—C8—H8C 106.8 (16) S1i—P1—Cl1 113.26 (3)
H8B—C8—H8C 109.0 (16) Cl1i—P1—Cl1 113.26 (3)
C6—C1—C2—C3 −0.8 (2) C5—C6—C7—C10 2.35 (18)
O1—C1—C2—C3 −178.73 (11) C1—C6—C7—C8 −60.70 (16)
C1—C2—C3—C4 1.4 (2) C5—C6—C7—C8 120.51 (13)
C2—C3—C4—O2 178.39 (11) C1—C6—C7—C9 61.76 (16)
C2—C3—C4—C5 −1.14 (19) C5—C6—C7—C9 −117.03 (14)
O2—C4—C5—C6 −179.21 (11) C2—C1—O1—P1 −40.07 (15)
C3—C4—C5—C6 0.28 (19) C6—C1—O1—P1 141.89 (10)
C2—C1—C6—C5 −0.05 (18) C3—C4—O2—C11 −176.65 (12)
O1—C1—C6—C5 177.90 (10) C5—C4—O2—C11 2.86 (18)
C2—C1—C6—C7 −178.90 (12) C1—O1—P1—O1i −155.66 (11)
O1—C1—C6—C7 −0.95 (18) C1—O1—P1—S1i 88.01 (9)
C4—C5—C6—C1 0.31 (18) C1—O1—P1—Cl1i 88.01 (9)
C4—C5—C6—C7 179.19 (12) C1—O1—P1—Cl1 −39.46 (10)
C1—C6—C7—C10 −178.86 (13)
organic papers
o2528
Odabas¸og˘luet al. C22H30ClO4PS doi:10.1107/S1600536805021860 Acta Cryst.(2005). E61, o2528–o2530
Acta Crystallographica Section E
Structure Reports Online
ISSN 1600-5368
O
,
O
-Bis(2-
tert
-butyl-4-methoxyphenyl)
chlorothiophosphonate
Mustafa Odabas¸og˘lu,a* Orhan Bu¨yu¨kgu¨ngo¨rb and C¸ig˘dem Albayraka
aDepartment of Chemistry, Ondokuz Mayıs
University, TR-55139 Samsun, Turkey, and
bDepartment of Physics, Ondokuz Mayıs
University, TR-55139 Samsun, Turkey
Correspondence e-mail: [email protected]
Key indicators
Single-crystal X-ray study T= 150 K
Mean(C–C) = 0.007 A˚ Rfactor = 0.027 wRfactor = 0.073
Data-to-parameter ratio = 17.1
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2005 International Union of Crystallography
Printed in Great Britain – all rights reserved
The title compound, C22H30ClO4PS, displays distorted tetra-hedral geometry around the P atom. The ditetra-hedral angle between the benzene rings is 41.2 (2). Because of the steric effects of the tert-butyl groups, the aromatic rings have unusual endocyclic angles. The molecules are linked by weak C—H interactions.
Comment
In the course of a systematic structural investigation of thio-phosphorus compounds, the structure of the title compound, (I), was determined. This investigation brings another contribution to our previous studies (Odabas¸og˘luet al., 1992, 1999, 2005; Yılmaz et al., 1998; Bu¨yu¨kgu¨ngo¨r et al., 1995; Odabas¸og˘lu & Gu¨mru¨kc¸uog˘lu, 1993).
An ORTEP-3(Farrugia, 1997) view of (I) and a packing diagram are shown in Figs. 1 and 2, respectively. Compound (I) has no classical hydrogen bonds but there are two C—H interactions: H31A Cg1 = 2.726 A˚ and C31—H31A Cg1 = 144 (Cg1 is the centroid of the C1i
–C6i ring), and H11A Cg2 = 2.764 A˚ and C31—H31A Cg1 = 141[Cg2 is the centroid of the C21ii–C26iiring; symmetry codes: (i)x1
2, 1
2y,z 1 2; (ii)
1 2þx,
1 2y,
1
2þz]. The dihedral angle between the benzene rings in (I) is 41.2 (2). Selected bond distances and angles for (I) are given in Table 1. As in O,O
[image:8.610.219.447.346.448.2] [image:8.610.207.461.611.714.2]-Received 1 July 2005 Accepted 7 July 2005 Online 13 July 2005
Figure 1
bis(2-tert-butyl-4-methoxylphenyl)phosphorochloridothioate (Odabas¸og˘lu et al., 2005), the C1—C6—C5, C3—C4—C5, C21—C26—C25 and C23—C24—C25 angles and C—C bond distances (Table 1) in the benzene rings are unusual; the diversity of the angles is probably due to steric effects of the tert-butyl groups.
The geometry about the P atom corresponds to a distorted tetrahedron, with the O—P—O angles smaller than the ideal tetrahedral angle of 109.5 (Table 1). The P S and P—O bond lengths agrees with those reported previously ( Inter-national Tables for X-ray Crystallography, 1983, Vol. III; Odabas¸og˘lu et al., 1992, 2005; Yılmaz et al., 1998; Bu¨yu¨k-gu¨ngo¨ret al., 1995).
Experimental
Compound (I) was prepared by the method of Odabas¸og˘lu et al. (2005), using 2-tert-butyl-4-methoxyphenol and PSCl3 as starting
materials. Crystals of (I) suitable for single-crystal X-ray diffraction were grown by slow evaporation of a solution inn-hexane (yield 77%, m.p. 423 K). Analysis calculated: C 57.83, H 6.57%; found: C 57.36, H 6.38%.
Crystal data
C22H30ClO4PS
Mr= 456.94
Monoclinic,Cc a= 23.592 (3) A˚
b= 8.3111 (6) A˚
c= 12.5067 (14) A˚ = 105.740 (9) V= 2360.3 (4) A˚3
Z= 4
Dx= 1.286 Mg m
3 MoKradiation
Cell parameters from 16485 reflections
= 1.7–26.7
= 0.34 mm1
T= 150 K Prism, colourless 0.640.590.55 mm
Data collection
Stoe IPDS-II diffractometer !scans
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)
Tmin= 0.824,Tmax= 0.869 16485 measured reflections 4630 independent reflections
4160 reflections withI> 2(I)
Rint= 0.032 max= 26.0
h=28!28
k=10!10
l=15!15
Refinement
Refinement onF2
R[F2> 2(F2)] = 0.027
wR(F2) = 0.074
S= 1.12 4630 reflections 270 parameters
H-atom parameters constrained
w= 1/[2(F
o2) + (0.0348P)2 + 1.103P]
whereP= (Fo2+ 2Fc2)/3
(/)max< 0.001 max= 0.18 e A˚
3 min=0.23 e A˚
3
Extinction correction:SHELXL97
Extinction coefficient: 0.0038 (3) Absolute structure: Flack (1983),
[image:9.610.46.294.71.277.2] [image:9.610.312.566.298.471.2]with 2303 Friedel pairs Flack parameter = 0.51 (1)
Table 1
Selected geometric parameters (A˚ ,).
C1—C6 1.373 (6)
C1—O1 1.402 (5)
C1—C2 1.446 (5)
C2—C3 1.347 (6)
C3—C4 1.463 (6)
C4—C5 1.338 (6)
C5—C6 1.412 (5)
C21—C22 1.372 (5)
C21—O3 1.451 (5)
C22—C23 1.465 (6)
C23—C24 1.330 (6)
C24—C25 1.457 (5)
C25—C26 1.355 (6)
O1—P1 1.583 (3)
O3—P1 1.564 (3)
P1—S1 1.9740 (18)
P1—Cl1 1.9848 (18)
C6—C1—O1 121.8 (4)
C6—C1—C2 121.0 (4)
O1—C1—C2 117.2 (4)
C3—C2—C1 117.9 (4)
C2—C3—C4 120.7 (4)
C5—C4—C3 120.1 (4)
C4—C5—C6 120.3 (4)
C1—C6—C5 119.9 (4)
C22—C21—O3 118.0 (3)
C23—C24—C25 120.7 (4)
C26—C25—C24 118.0 (4)
C25—C26—C21 119.3 (4)
C21—O3—P1 126.4 (3)
C24—O4—C31 115.9 (3)
O3—P1—O1 97.13 (5)
O3—P1—S1 112.66 (14)
O1—P1—S1 112.02 (15)
O3—P1—Cl1 110.44 (15)
O1—P1—Cl1 110.26 (14)
S1—P1—Cl1 113.24 (2)
All H atoms were refined using a riding model, with C—H = 0.93 A˚ [Uiso(H) = 1.2Ueq(parent atom)] for aromatic H atoms and C—H =
0.96 A˚ [Uiso(H) = 1.5Ueq(parent atom)] for methyl H atoms. The
crystal investigated was an inversion twin. The ratio of the two twin components refined to 0.51 (1):0.49 (1).
Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction:X-RED32(Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97(Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics:ORTEP-3 for Windows(Farrugia, 1997); software used to prepare material for publication:WinGX(Farrugia, 1999).
References
Bu¨yu¨kgu¨ngo¨r, O., Odabas¸og˘lu, M., Gu¨mru¨kc¸u¨og˘lu, I˙. E., Eichhorn, E. & Mattern, G. (1995).Acta Cryst.C51, 1207–1209.
Farrugia, L. J. (1997).J. Appl. Cryst.30, 565. Farrugia, L. J. (1999).J. Appl. Cryst.32, 837–838. Flack, H. D. (1983).Acta Cryst.A39, 876–881.
Odabas¸og˘lu, M., Bu¨yu¨kgu¨ngo¨r, O. & Albayrak, C¸ . (2005).Acta Cryst.E61, o2525–o2527.
Odabas¸og˘lu, M. & Gu¨mru¨kc¸u¨og˘lu, I˙. E. (1993).Dog˘a Turk. J. Chem.17, 29– 32.
Odabas¸og˘lu, M., Gu¨mru¨kc¸u¨og˘lu, I˙. E. & Taprama, R. (1999).Phosphorus, Sulfur and Silicon,152, 27–34.
organic papers
Acta Cryst.(2005). E61, o2528–o2530 Odabas¸og˘luet al. C
22H30ClO4PS
o2529
Figure 2
Odabas¸og˘lu, M., Gu¨mru¨kc¸u¨og˘lu, I˙. E., Yılmaz, V. T. & Howie, R. A. (1992).
Dog˘a Turk. J. Chem.16, 293–298.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Go¨ttingen, Germany.
Stoe & Cie (2002).X-AREA(Version 1.18) andX-RED32(Version 1.04). Stoe & Cie, Darmstadt, Germany.
Yılmaz, V. T., Odabas¸og˘lu, M. & Howie, R. A. (1998).Dog˘a Turk. J. Chem.22, 409–413.
organic papers
o2530
Odabas¸og˘luet al. Csupporting information
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Acta Cryst. (2005). E61, o2528–o2530
supporting information
Acta Cryst. (2005). E61, o2528–o2530 [https://doi.org/10.1107/S1600536805021860]
O
,
O
-Bis(2-
tert
-butyl-4-methoxyphenyl) chlorothiophosphonate
Mustafa Odaba
ş
o
ğ
lu, Orhan B
ü
y
ü
kg
ü
ng
ö
r and
Ç
i
ğ
dem Albayrak
O,O-Bis(2-tert-butyl-4-methoxyphenyl) chlorothiophosphonate
Crystal data
C22H30ClO4PS
Mr = 456.94 Monoclinic, Cc
Hall symbol: C-2yc
a = 23.592 (3) Å
b = 8.3111 (6) Å
c = 12.5067 (14) Å
β = 105.740 (9)°
V = 2360.3 (4) Å3
Z = 4
F(000) = 968
Dx = 1.286 Mg m−3
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 16485 reflections
θ = 1.7–26.7°
µ = 0.34 mm−1
T = 150 K Prism, colorless 0.64 × 0.59 × 0.55 mm
Data collection
Stoe IPDS-II diffractometer
Graphite monochromator
ω scans
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)
Tmin = 0.824, Tmax = 0.869 16485 measured reflections
4630 independent reflections 4160 reflections with I > 2σ(I)
Rint = 0.032
θmax = 26.0°, θmin = 1.8°
h = −28→28
k = −10→10
l = −15→15
Refinement
Refinement on F2 Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.027
wR(F2) = 0.074
S = 1.12 4630 reflections 270 parameters 2 restraints
Primary atom site location: structure-invariant direct methods
Secondary atom site location: difference Fourier map
Hydrogen site location: inferred from neighbouring sites
H-atom parameters constrained
w = 1/[σ2(F
o2) + (0.0348P)2 + 1.103P] where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001 Δρmax = 0.18 e Å−3 Δρmin = −0.23 e Å−3
Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 Extinction coefficient: 0.0038 (3) Absolute structure: Flack (1983)
Special details
supporting information
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Acta Cryst. (2005). E61, o2528–o2530
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x y z Uiso*/Ueq
C1 0.61457 (18) 0.2884 (5) 0.7043 (4) 0.0233 (9)
C2 0.65778 (19) 0.4160 (5) 0.7298 (4) 0.0247 (9)
C3 0.70775 (18) 0.3899 (5) 0.8108 (4) 0.0248 (9)
H3 0.7358 0.4711 0.8302 0.030*
C4 0.71839 (19) 0.2351 (5) 0.8684 (4) 0.0247 (9)
C5 0.67790 (18) 0.1184 (5) 0.8424 (3) 0.0278 (9)
H5 0.6846 0.0206 0.8798 0.033*
C6 0.62496 (18) 0.1431 (5) 0.7584 (4) 0.0255 (9)
H6 0.5972 0.0612 0.7397 0.031*
C7 0.6451 (2) 0.5797 (5) 0.6695 (4) 0.0303 (10)
C8 0.6370 (2) 0.5587 (6) 0.5439 (5) 0.0422 (13)
H8A 0.6272 0.6606 0.5073 0.063*
H8B 0.6058 0.4833 0.5146 0.063*
H8C 0.6729 0.5193 0.5314 0.063*
C9 0.5908 (2) 0.6681 (6) 0.6915 (5) 0.0426 (12)
H9A 0.5835 0.7661 0.6494 0.064*
H9B 0.5987 0.6925 0.7692 0.064*
H9C 0.5567 0.5999 0.6695 0.064*
C10 0.6987 (2) 0.6971 (5) 0.7079 (5) 0.0448 (13)
H10A 0.7327 0.6502 0.6920 0.067*
H10B 0.7066 0.7159 0.7863 0.067*
H10C 0.6895 0.7973 0.6688 0.067*
C11 0.81095 (19) 0.3284 (6) 0.9857 (4) 0.0352 (11)
H11A 0.8262 0.3593 0.9249 0.053*
H11B 0.8426 0.2911 1.0463 0.053*
H11C 0.7924 0.4194 1.0093 0.053*
C21 0.43699 (17) 0.2962 (5) 0.3639 (3) 0.0221 (9)
C22 0.39781 (17) 0.4218 (5) 0.3432 (4) 0.0218 (8)
C23 0.34387 (17) 0.3852 (6) 0.2561 (4) 0.0262 (9)
H23 0.3148 0.4637 0.2374 0.031*
C24 0.33435 (18) 0.2455 (5) 0.2022 (4) 0.0258 (9)
C25 0.37774 (17) 0.1167 (5) 0.2299 (4) 0.0275 (9)
H25 0.3705 0.0171 0.1950 0.033*
C26 0.42902 (19) 0.1464 (5) 0.3079 (4) 0.0266 (9)
H26 0.4587 0.0692 0.3246 0.032*
C27 0.4071 (2) 0.5872 (5) 0.4031 (4) 0.0288 (10)
C28 0.3544 (2) 0.6996 (6) 0.3601 (5) 0.0480 (15)
H28A 0.3482 0.7171 0.2819 0.072*
H28B 0.3620 0.8007 0.3985 0.072*
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C29 0.4615 (2) 0.6646 (6) 0.3781 (4) 0.0393 (12)
H29A 0.4555 0.6709 0.2992 0.059*
H29B 0.4957 0.6004 0.4103 0.059*
H29C 0.4671 0.7709 0.4093 0.059*
C30 0.4163 (2) 0.5632 (5) 0.5296 (4) 0.0339 (11)
H30A 0.4193 0.6663 0.5654 0.051*
H30B 0.4519 0.5035 0.5599 0.051*
H30C 0.3835 0.5051 0.5420 0.051*
C31 0.24133 (18) 0.3299 (6) 0.0825 (4) 0.0361 (11)
H31A 0.2253 0.3564 0.1431 0.054*
H31B 0.2104 0.2923 0.0207 0.054*
H31C 0.2592 0.4238 0.0609 0.054*
O1 0.56202 (13) 0.3195 (4) 0.6223 (3) 0.0260 (7)
O2 0.76883 (13) 0.2027 (4) 0.9508 (3) 0.0324 (8)
O3 0.49314 (14) 0.3197 (4) 0.4458 (3) 0.0260 (7)
O4 0.28530 (14) 0.2050 (4) 0.1170 (3) 0.0323 (8)
P1 0.52627 (7) 0.19436 (4) 0.53408 (15) 0.02670 (10)
S1 0.47221 (3) 0.06319 (14) 0.59405 (6) 0.0310 (2)
Cl1 0.58094 (3) 0.06347 (14) 0.47391 (6) 0.0333 (3)
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
C1 0.0212 (18) 0.0200 (17) 0.028 (2) −0.0072 (14) 0.0050 (17) −0.0089 (15)
C2 0.030 (2) 0.0183 (17) 0.027 (2) −0.0026 (15) 0.0107 (17) 0.0007 (15)
C3 0.032 (2) 0.0196 (18) 0.026 (2) −0.0043 (16) 0.0131 (17) −0.0005 (16)
C4 0.031 (2) 0.0233 (18) 0.0188 (19) 0.0071 (15) 0.0050 (16) 0.0058 (14)
C5 0.031 (2) 0.032 (2) 0.0151 (18) 0.0094 (16) −0.0026 (15) 0.0054 (15)
C6 0.0203 (19) 0.029 (2) 0.025 (2) −0.0026 (17) 0.0009 (16) 0.0022 (18)
C7 0.030 (2) 0.025 (2) 0.031 (2) −0.0076 (16) 0.0018 (18) −0.0044 (16)
C8 0.043 (3) 0.033 (2) 0.051 (3) −0.0048 (19) 0.014 (2) 0.017 (2)
C9 0.034 (2) 0.030 (2) 0.061 (3) 0.0113 (19) 0.008 (2) −0.002 (2)
C10 0.052 (3) 0.026 (2) 0.050 (3) −0.007 (2) 0.003 (3) −0.001 (2)
C11 0.030 (2) 0.040 (2) 0.033 (3) 0.0088 (18) 0.0044 (19) −0.008 (2)
C21 0.0208 (18) 0.029 (2) 0.0136 (18) −0.0064 (15) −0.0008 (15) −0.0056 (14)
C22 0.0191 (18) 0.0264 (19) 0.0177 (18) −0.0007 (14) 0.0012 (14) 0.0044 (14)
C23 0.0169 (16) 0.032 (2) 0.025 (2) 0.0040 (16) −0.0022 (15) 0.0073 (18)
C24 0.0156 (16) 0.038 (2) 0.022 (2) 0.0076 (15) 0.0020 (15) 0.0110 (16)
C25 0.028 (2) 0.0211 (19) 0.034 (2) 0.0088 (15) 0.0098 (17) −0.0007 (16)
C26 0.030 (2) 0.022 (2) 0.027 (2) 0.0067 (17) 0.0070 (18) 0.0021 (17)
C27 0.033 (2) 0.0173 (17) 0.035 (2) 0.0005 (16) 0.0067 (18) −0.0087 (15)
C28 0.038 (3) 0.032 (3) 0.064 (4) 0.017 (2) −0.004 (3) −0.015 (2)
C29 0.057 (3) 0.0195 (19) 0.039 (3) 0.002 (2) 0.009 (2) 0.0026 (19)
C30 0.045 (3) 0.034 (2) 0.0201 (19) 0.0029 (19) 0.0051 (18) −0.0041 (16)
C31 0.023 (2) 0.043 (3) 0.033 (3) 0.0120 (18) −0.0083 (18) 0.009 (2)
O1 0.0192 (14) 0.0256 (15) 0.0272 (16) 0.0020 (11) −0.0038 (12) −0.0011 (11)
O2 0.0215 (15) 0.0403 (19) 0.0300 (19) −0.0026 (13) −0.0023 (14) 0.0009 (14)
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Acta Cryst. (2005). E61, o2528–o2530
O4 0.0294 (16) 0.0328 (18) 0.0275 (18) 0.0006 (13) −0.0046 (15) −0.0007 (13)
P1 0.02940 (19) 0.01983 (17) 0.02479 (18) −0.0009 (6) −0.00303 (14) −0.0009 (6)
S1 0.0249 (5) 0.0366 (6) 0.0313 (6) −0.0061 (4) 0.0070 (4) 0.0018 (5)
Cl1 0.0286 (6) 0.0384 (6) 0.0333 (6) 0.0069 (4) 0.0092 (5) −0.0030 (5)
Geometric parameters (Å, º)
C1—C6 1.373 (6) C21—O3 1.451 (5)
C1—O1 1.402 (5) C22—C23 1.465 (6)
C1—C2 1.446 (5) C22—C27 1.553 (6)
C2—C3 1.347 (6) C23—C24 1.330 (6)
C2—C7 1.545 (6) C23—H23 0.9300
C3—C4 1.463 (6) C24—O4 1.385 (5)
C3—H3 0.9300 C24—C25 1.457 (5)
C4—C5 1.338 (6) C25—C26 1.355 (6)
C4—O2 1.373 (5) C25—H25 0.9300
C5—C6 1.412 (5) C26—H26 0.9300
C5—H5 0.9300 C27—C28 1.533 (6)
C6—H6 0.9300 C27—C29 1.540 (7)
C7—C8 1.540 (8) C27—C30 1.551 (7)
C7—C10 1.565 (6) C28—H28A 0.9600
C7—C9 1.566 (7) C28—H28B 0.9600
C8—H8A 0.9600 C28—H28C 0.9600
C8—H8B 0.9600 C29—H29A 0.9600
C8—H8C 0.9600 C29—H29B 0.9600
C9—H9A 0.9600 C29—H29C 0.9600
C9—H9B 0.9600 C30—H30A 0.9600
C9—H9C 0.9600 C30—H30B 0.9600
C10—H10A 0.9600 C30—H30C 0.9600
C10—H10B 0.9600 C31—O4 1.448 (5)
C10—H10C 0.9600 C31—H31A 0.9600
C11—O2 1.427 (6) C31—H31B 0.9600
C11—H11A 0.9600 C31—H31C 0.9600
C11—H11B 0.9600 O1—P1 1.583 (3)
C11—H11C 0.9600 O3—P1 1.564 (3)
C21—C22 1.372 (5) P1—S1 1.9740 (18)
C21—C26 1.416 (6) P1—Cl1 1.9848 (18)
C6—C1—O1 121.8 (4) C23—C22—C27 121.6 (4)
C6—C1—C2 121.0 (4) C24—C23—C22 123.4 (4)
O1—C1—C2 117.2 (4) C24—C23—H23 118.3
C3—C2—C1 117.9 (4) C22—C23—H23 118.3
C3—C2—C7 121.5 (4) C23—C24—O4 126.3 (4)
C1—C2—C7 120.5 (4) C23—C24—C25 120.7 (4)
C2—C3—C4 120.7 (4) O4—C24—C25 113.0 (4)
C2—C3—H3 119.7 C26—C25—C24 118.0 (4)
C4—C3—H3 119.7 C26—C25—H25 121.0
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C5—C4—C3 120.1 (4) C25—C26—C21 119.3 (4)
O2—C4—C3 122.7 (4) C25—C26—H26 120.4
C4—C5—C6 120.3 (4) C21—C26—H26 120.4
C4—C5—H5 119.8 C28—C27—C29 108.4 (4)
C6—C5—H5 119.8 C28—C27—C30 108.1 (4)
C1—C6—C5 119.9 (4) C29—C27—C30 111.5 (4)
C1—C6—H6 120.1 C28—C27—C22 112.0 (4)
C5—C6—H6 120.1 C29—C27—C22 106.8 (4)
C8—C7—C2 110.7 (4) C30—C27—C22 109.9 (4)
C8—C7—C10 104.5 (4) C27—C28—H28A 109.5
C2—C7—C10 111.5 (4) C27—C28—H28B 109.5
C8—C7—C9 110.6 (4) H28A—C28—H28B 109.5
C2—C7—C9 112.7 (4) C27—C28—H28C 109.5
C10—C7—C9 106.5 (4) H28A—C28—H28C 109.5
C7—C8—H8A 109.5 H28B—C28—H28C 109.5
C7—C8—H8B 109.5 C27—C29—H29A 109.5
H8A—C8—H8B 109.5 C27—C29—H29B 109.5
C7—C8—H8C 109.5 H29A—C29—H29B 109.5
H8A—C8—H8C 109.5 C27—C29—H29C 109.5
H8B—C8—H8C 109.5 H29A—C29—H29C 109.5
C7—C9—H9A 109.5 H29B—C29—H29C 109.5
C7—C9—H9B 109.5 C27—C30—H30A 109.5
H9A—C9—H9B 109.5 C27—C30—H30B 109.5
C7—C9—H9C 109.5 H30A—C30—H30B 109.5
H9A—C9—H9C 109.5 C27—C30—H30C 109.5
H9B—C9—H9C 109.5 H30A—C30—H30C 109.5
C7—C10—H10A 109.5 H30B—C30—H30C 109.5
C7—C10—H10B 109.5 O4—C31—H31A 109.5
H10A—C10—H10B 109.5 O4—C31—H31B 109.5
C7—C10—H10C 109.5 H31A—C31—H31B 109.5
H10A—C10—H10C 109.5 O4—C31—H31C 109.5
H10B—C10—H10C 109.5 H31A—C31—H31C 109.5
O2—C11—H11A 109.5 H31B—C31—H31C 109.5
O2—C11—H11B 109.5 C1—O1—P1 126.0 (3)
H11A—C11—H11B 109.5 C4—O2—C11 118.4 (4)
O2—C11—H11C 109.5 C21—O3—P1 126.4 (3)
H11A—C11—H11C 109.5 C24—O4—C31 115.9 (3)
H11B—C11—H11C 109.5 O3—P1—O1 97.13 (5)
C22—C21—C26 125.7 (4) O3—P1—S1 112.66 (14)
C22—C21—O3 118.0 (3) O1—P1—S1 112.02 (15)
C26—C21—O3 116.2 (4) O3—P1—Cl1 110.44 (15)
C21—C22—C23 112.8 (4) O1—P1—Cl1 110.26 (14)
C21—C22—C27 125.6 (4) S1—P1—Cl1 113.24 (2)
C6—C1—C2—C3 −2.2 (7) C22—C23—C24—C25 1.6 (7)
O1—C1—C2—C3 178.0 (4) C23—C24—C25—C26 −3.1 (7)
C6—C1—C2—C7 −179.2 (4) O4—C24—C25—C26 176.4 (4)
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Acta Cryst. (2005). E61, o2528–o2530
C1—C2—C3—C4 1.8 (6) C22—C21—C26—C25 −3.2 (7)
C7—C2—C3—C4 178.8 (4) O3—C21—C26—C25 −179.6 (4)
C2—C3—C4—C5 −1.2 (7) C21—C22—C27—C28 −179.6 (5)
C2—C3—C4—O2 179.5 (4) C23—C22—C27—C28 0.2 (7)
O2—C4—C5—C6 −179.9 (4) C21—C22—C27—C29 61.8 (6)
C3—C4—C5—C6 0.8 (7) C23—C22—C27—C29 −118.4 (4)
O1—C1—C6—C5 −178.4 (4) C21—C22—C27—C30 −59.3 (6)
C2—C1—C6—C5 1.7 (7) C23—C22—C27—C30 120.5 (5)
C4—C5—C6—C1 −1.1 (7) C6—C1—O1—P1 −36.4 (6)
C3—C2—C7—C8 120.6 (5) C2—C1—O1—P1 143.4 (3)
C1—C2—C7—C8 −62.5 (6) C5—C4—O2—C11 −175.7 (4)
C3—C2—C7—C10 4.7 (7) C3—C4—O2—C11 3.7 (6)
C1—C2—C7—C10 −178.4 (4) C22—C21—O3—P1 139.9 (4)
C3—C2—C7—C9 −115.0 (5) C26—C21—O3—P1 −43.4 (5)
C1—C2—C7—C9 61.9 (6) C23—C24—O4—C31 1.7 (6)
C26—C21—C22—C23 1.5 (6) C25—C24—O4—C31 −177.8 (4)
O3—C21—C22—C23 177.8 (4) C21—O3—P1—O1 −154.2 (3)
C26—C21—C22—C27 −178.7 (4) C21—O3—P1—S1 −36.7 (4)
O3—C21—C22—C27 −2.4 (7) C21—O3—P1—Cl1 91.0 (3)
C21—C22—C23—C24 −0.7 (6) C1—O1—P1—O3 −157.0 (3)
C27—C22—C23—C24 179.5 (4) C1—O1—P1—S1 85.0 (3)
