Acta Cryst.(2001). E57, o147±o148 DOI: 101107/S1600536801001404 Lynch and McClenaghan C11H8ClNO2
o147
organic papers
Acta Crystallographica Section E Structure Reports Online
ISSN 1600-5368
1-(3-Chloro-4-methylphenyl)-3-pyrroline-2,5-dione
Daniel E. Lyncha* and Ian McClenaghanb²
aSchool of Natural and Environmental Sciences,
Coventry University, Coventry CV1 5FB, England, andbSpa Contract Synthesis, School of
Natural and Environmental Sciences, Coventry University, Coventry CV1 5FB, England
² E-mail: [email protected].
Correspondence e-mail: [email protected]
Key indicators Single-crystal X-ray study T= 150 K
Mean(C±C) = 0.004 AÊ Rfactor = 0.052 wRfactor = 0.131
Data-to-parameter ratio = 15.2
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2001 International Union of Crystallography Printed in Great Britain ± all rights reserved
The structure of the title compound, C11H8ClNO2, (I), comprises a twisted molecule with the dihedral angle between the two rings being 49.9 (2). Several CÐH Xshort contacts
exist to both O atoms, but not to the Cl atom. The resultant structure packs in a noncentrosymmetric space group (Pna21) and the bulk material exhibits a second harmonic signal ofI/
Iurea= 0.09.
Experimental
The title compound, (I), was prepared by Spa Contract Synthesis. Crystals of (I) were grown from an acetone solution.
Crystal data
C11H8ClNO2
Mr= 221.63
Orthorhombic,Pna21
a= 10.473 (2) AÊ
b= 24.303 (5) AÊ
c= 3.8594 (8) AÊ
V= 982.3 (3) AÊ3
Z= 4
Dx= 1.499 Mg mÿ3
MoKradiation Cell parameters from 4247
re¯ections
= 2.9±39.4 = 0.36 mmÿ1
T= 150 (2) K Needle, yellow 0.550.050.05 mm
Data collection
Enraf±Nonius KappaCCD area-detector diffractometer
'and!scans
Absorption correction: multi-scan (SORTAV; Blessing, 1995)
Tmin= 0.825,Tmax= 0.982
6579 measured re¯ections
2076 independent re¯ections 1583 re¯ections withI> 2(I)
Rint= 0.091
max= 27.5
h= 0!13
k= 0!31
l=ÿ4!4
Re®nement
Re®nement onF2
R[F2> 2(F2)] = 0.052
wR(F2) = 0.131
S= 1.00 2076 re¯ections 137 parameters
H-atom parameters constrained
w= 1/[2(F
o2) + (0.0742P)2]
whereP= (Fo2+ 2Fc2)/3
(/)max< 0.001
max= 0.49 e AÊÿ3
min=ÿ0.37 e AÊÿ3
Absolute structure: Flack (1983) Flack parameter = 0.28 (11)
Table 1
Hydrogen-bonding geometry (AÊ,).
DÐH A DÐH H A D A DÐH A
C3ÐH3 O2i 0.95 2.52 3.150 (4) 124
C7ÐH7 O2ii 0.95 2.59 3.325 (4) 135
C10ÐH10 O5iii 0.95 2.57 3.480 (4) 160
Symmetry codes: (i)1
2x;12ÿy;z; (ii)x;y;zÿ1; (iii) 1ÿx;1ÿy;12z.
All H atoms were included in the re®nement at calculated posi-tions as riding models with CÐH set to 0.95 (Ar-H) and 0.98 AÊ (CH3). The number of Friedel pairs is 560.
Data collection: DENZO (Otwinowski & Minor, 1997) and
COLLECT(Hooft, 1998); cell re®nement:DENZOandCOLLECT; data reduction:DENZOandCOLLECT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to re®ne structure: SHELXL97 (Sheldrick, 1997); molecular graphics:
PLATON97 (Spek, 1990); software used to prepare material for publication:SHELXL97.
The authors thank the EPSRC National Crystallography Service (Southampton).
References
Blessing, R. H. (1995).Acta Cryst.A51, 33±37. Flack, H. D. (1983).Acta Cryst.A39, 876±881.
Hooft, R. (1998).COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997).Methods Enzymol.276, 307±326. Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of
GoÈttingen, Germany.
Spek, A. L. (1990).Acta Cryst.A46, C-34.
Figure 1
supporting information
sup-1
Acta Cryst. (2001). E57, o147–o148
supporting information
Acta Cryst. (2001). E57, o147–o148 [doi:10.1107/S1600536801001404]
1-(3-Chloro-4-methylphenyl)-3-pyrroline-2,5-dione
Daniel E. Lynch and Ian McClenaghan
S1. Comment
NO COMMENT
S2. Experimental
The title compound, (I), was prepared by Spa Contract Synthesis. Crystals of (I) were grown from an acetone solution.
S3. Refinement
All H atoms were included in the refinement at calculated positions as riding models with C—H set to 0.95 (Ar—H) and
[image:3.610.128.485.342.559.2]0.98 Å (CH3). The number of Friedel pairs is 560.
Figure 1
The molecular configuration and atom numbering scheme for (I), showing 50% probability ellipsoids.
1-(3-Chloro-4-methylphenyl)pyrroline-2,5-dione
Crystal data
C11H8ClNO2
Mr = 221.63
Orthorhombic, Pna21
a = 10.473 (2) Å
b = 24.303 (5) Å
c = 3.8594 (8) Å
V = 982.3 (3) Å3
Z = 4
F(000) = 456
Dx = 1.499 Mg m−3
Melting point: 413-413.5 K K Mo Kα radiation, λ = 0.71073 Å Cell parameters from 4247 reflections
µ = 0.36 mm−1
T = 150 K
Needle, yellow 0.55 × 0.05 × 0.05 mm
Data collection
Enraf Nonius KappaCCD area-detector diffractometer
Radiation source: Enraf Nonius FR591 rotating anode
Graphite monochromator
Detector resolution: 9.091 pixels mm-1
φ and ω scans
Absorption correction: multi-scan (SORTAV; Blessing, 1995)
Tmin = 0.825, Tmax = 0.982
6579 measured reflections 2076 independent reflections 1583 reflections with I > 2σ(I)
Rint = 0.091
θmax = 27.5°, θmin = 3.2°
h = 0→13
k = 0→31
l = −4→4
Refinement
Refinement on F2
Least-squares matrix: full
R[F2 > 2σ(F2)] = 0.052
wR(F2) = 0.131
S = 1.00 2076 reflections 137 parameters 1 restraint
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) + (0.0742P)2]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.49 e Å−3
Δρmin = −0.37 e Å−3
Absolute structure: Flack (1983) Absolute structure parameter: 0.28 (11)
Special details
Experimental. PLEASE NOTE cell_measurement_ fields are not relevant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range.
Geometry. Mean plane data ex SHELXL97 ###########################
Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) 0.9742 (0.0184) x + 9.8588 (0.0416) y + 3.5093 (0.0032) z = 6.8087 (0.0172)
* 0.0050 (0.0021) N1 * -0.0016 (0.0021) C2 * -0.0025 (0.0024) C3 * 0.0054 (0.0024) C4 * -0.0062 (0.0021) C5 Rms deviation of fitted atoms = 0.0045
2.9354 (0.0144) x + 8.5212 (0.0291) y - 3.4487 (0.0025) z = 2.0297 (0.0144) Angle to previous plane (with approximate e.s.d.) = 49.89 (0.09)
* 0.0015 (0.0022) C6 * 0.0015 (0.0023) C7 * -0.0036 (0.0023) C8 * 0.0027 (0.0023) C9 * 0.0002 (0.0026) C10 * -0.0023 (0.0024) C11
Rms deviation of fitted atoms = 0.0022
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)
x y z Uiso*/Ueq
N1 0.6048 (3) 0.34814 (10) 0.7957 (7) 0.0263 (7)
C2 0.6172 (3) 0.29531 (13) 0.9388 (9) 0.0265 (7)
O2 0.5295 (2) 0.26786 (9) 1.0459 (7) 0.0329 (6)
C3 0.7553 (3) 0.28254 (13) 0.9360 (10) 0.0300 (8)
H3 0.7927 0.2493 1.0174 0.038*
C4 0.8180 (3) 0.32409 (15) 0.8042 (9) 0.0358 (9)
H4 0.9080 0.3260 0.7769 0.045*
supporting information
sup-3
Acta Cryst. (2001). E57, o147–o148
O5 0.7472 (2) 0.41149 (10) 0.5664 (8) 0.0452 (7)
C6 0.4875 (3) 0.37742 (12) 0.7585 (9) 0.0234 (7)
C7 0.3849 (3) 0.35109 (12) 0.6061 (8) 0.0242 (7)
H7 0.3931 0.3145 0.5218 0.030*
C8 0.2704 (3) 0.37884 (12) 0.5787 (8) 0.0241 (7)
Cl8 0.14304 (7) 0.34360 (3) 0.3922 (3) 0.0320 (2)
C9 0.2546 (3) 0.43270 (13) 0.6965 (8) 0.0262 (7)
C10 0.3599 (3) 0.45747 (13) 0.8481 (9) 0.0257 (7)
H10 0.3522 0.4941 0.9320 0.032*
C11 0.4767 (3) 0.43050 (11) 0.8816 (10) 0.0275 (7)
H11 0.5474 0.4483 0.9871 0.034*
C12 0.1308 (3) 0.46269 (16) 0.6597 (10) 0.0355 (9)
H121 0.1087 0.4657 0.4137 0.044*
H122 0.1390 0.4996 0.7594 0.044*
H123 0.0635 0.4425 0.7819 0.044*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
N1 0.0243 (15) 0.0187 (14) 0.0359 (19) 0.0001 (10) 0.0013 (11) 0.0037 (11)
C2 0.0348 (19) 0.0190 (16) 0.0258 (18) 0.0012 (14) 0.0020 (14) −0.0002 (14)
O2 0.0312 (13) 0.0221 (12) 0.0455 (13) −0.0001 (11) 0.0054 (10) 0.0060 (10)
C3 0.0289 (17) 0.0222 (16) 0.039 (2) 0.0068 (14) −0.0007 (15) 0.0023 (14)
C4 0.0275 (19) 0.032 (2) 0.048 (3) 0.0034 (15) 0.0025 (15) 0.0066 (16)
C5 0.033 (2) 0.0281 (19) 0.0394 (19) −0.0001 (16) 0.0007 (16) 0.0051 (15)
O5 0.0360 (15) 0.0275 (14) 0.0722 (19) −0.0013 (11) 0.0068 (14) 0.0197 (13)
C6 0.0239 (17) 0.0203 (15) 0.0262 (16) 0.0023 (14) 0.0019 (13) 0.0037 (11)
C7 0.0286 (18) 0.0196 (17) 0.0243 (18) 0.0000 (13) 0.0019 (13) 0.0002 (13)
C8 0.0267 (17) 0.0224 (16) 0.0233 (16) −0.0044 (14) 0.0001 (13) 0.0003 (12)
Cl8 0.0281 (4) 0.0350 (4) 0.0330 (4) −0.0040 (3) −0.0014 (4) −0.0035 (4)
C9 0.0299 (19) 0.0240 (17) 0.0248 (17) 0.0024 (14) 0.0049 (14) 0.0037 (14)
C10 0.0317 (18) 0.0184 (14) 0.0269 (19) 0.0018 (13) 0.0062 (13) 0.0015 (13)
C11 0.0324 (17) 0.0215 (15) 0.0286 (16) −0.0042 (13) 0.0000 (16) 0.0009 (15)
C12 0.040 (2) 0.029 (2) 0.037 (2) 0.0099 (16) −0.0013 (15) 0.0003 (14)
Geometric parameters (Å, º)
N1—C5 1.401 (4) C7—C8 1.380 (4)
N1—C2 1.404 (4) C7—H7 0.95
N1—C6 1.427 (4) C8—C9 1.396 (4)
C2—O2 1.208 (4) C8—Cl8 1.741 (3)
C2—C3 1.480 (4) C9—C10 1.386 (5)
C3—C4 1.307 (5) C9—C12 1.494 (4)
C3—H3 0.95 C10—C11 1.393 (4)
C4—C5 1.486 (5) C10—H10 0.95
C4—H4 0.95 C11—H11 0.95
C5—O5 1.208 (4) C12—H121 0.98
C6—C7 1.382 (5) C12—H123 0.98
C5—N1—C2 109.1 (3) C6—C7—H7 120.6
C5—N1—C6 125.7 (3) C7—C8—C9 122.4 (3)
C2—N1—C6 125.1 (3) C7—C8—Cl8 117.2 (2)
O2—C2—N1 124.7 (3) C9—C8—Cl8 120.4 (2)
O2—C2—C3 129.0 (3) C10—C9—C8 116.8 (3)
N1—C2—C3 106.2 (3) C10—C9—C12 121.2 (3)
C4—C3—C2 109.4 (3) C8—C9—C12 121.9 (3)
C4—C3—H3 125.3 C9—C10—C11 122.2 (3)
C2—C3—H3 125.3 C9—C10—H10 118.9
C3—C4—C5 109.2 (3) C11—C10—H10 118.9
C3—C4—H4 125.4 C6—C11—C10 118.7 (3)
C5—C4—H4 125.4 C6—C11—H11 120.6
O5—C5—N1 125.3 (3) C10—C11—H11 120.6
O5—C5—C4 128.6 (3) C9—C12—H121 109.5
N1—C5—C4 106.1 (3) C9—C12—H122 109.5
C11—C6—C7 121.0 (3) H121—C12—H122 109.5
C11—C6—N1 120.2 (3) C9—C12—H123 109.5
C7—C6—N1 118.8 (3) H121—C12—H123 109.5
C8—C7—C6 118.8 (3) H122—C12—H123 109.5
C8—C7—H7 120.6
C5—N1—C2—O2 179.2 (3) C5—N1—C6—C7 131.6 (3)
C6—N1—C2—O2 0.6 (5) C2—N1—C6—C7 −50.0 (5)
C5—N1—C2—C3 0.6 (4) C11—C6—C7—C8 0.0 (5)
C6—N1—C2—C3 −178.0 (3) N1—C6—C7—C8 178.2 (3)
O2—C2—C3—C4 −178.4 (4) C6—C7—C8—C9 0.6 (5)
N1—C2—C3—C4 0.1 (4) C6—C7—C8—Cl8 −178.9 (2)
C2—C3—C4—C5 −0.8 (4) C7—C8—C9—C10 −0.7 (5)
C2—N1—C5—O5 178.1 (4) Cl8—C8—C9—C10 178.7 (3)
C6—N1—C5—O5 −3.3 (6) C7—C8—C9—C12 178.9 (3)
C2—N1—C5—C4 −1.0 (4) Cl8—C8—C9—C12 −1.7 (4)
C6—N1—C5—C4 177.6 (3) C8—C9—C10—C11 0.3 (5)
C3—C4—C5—O5 −178.0 (4) C12—C9—C10—C11 −179.3 (3)
C3—C4—C5—N1 1.1 (4) C7—C6—C11—C10 −0.3 (5)
C5—N1—C6—C11 −50.1 (5) N1—C6—C11—C10 −178.6 (3)
C2—N1—C6—C11 128.3 (3) C9—C10—C11—C6 0.2 (5)
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
C3—H3···O2i 0.95 2.52 3.150 (4) 124
C7—H7···O2ii 0.95 2.59 3.325 (4) 135
C10—H10···O5iii 0.95 2.57 3.480 (4) 160
