organic papers
o1568
Gordon B. Riddleet al. C16H12N2O3 DOI: 10.1107/S1600536804020082 Acta Cryst.(2004). E60, o1568±o1570 Acta Crystallographica Section EStructure Reports
Online
ISSN 1600-5368
The sydnone compound
4-hydroxy-4-benzyl-sydno[3,4-a]indole
Gordon B. Riddle, David A. Grossie* and Kenneth Turnbull
Department of Chemistry, Wright State University, Dayton, Ohio 45435, USA
Correspondence e-mail: [email protected]
Key indicators
Single-crystal X-ray study T= 298 K
Mean(C±C) = 0.002 AÊ Rfactor = 0.045 wRfactor = 0.146
Data-to-parameter ratio = 15.8
For details of how these key indicators were automatically derived from the article, see http://journals.iucr.org/e.
#2004 International Union of Crystallography Printed in Great Britain ± all rights reserved
The title compound (systematic name: 9-benzyl-1,9-di-hydroxy-9H-indolo[1,2-c][1,2,3]oxadiazole), C16H12N2O3, was
synthesized as part of a series of sydnones to determine substituent effects on the sydnone ring. The are two independent molecules in the asymmetric unit. There is interest in ®nding substituents for the sydnone ring that would allow for the release of NOviaring opening. Observed bond distances and angles for the sydnone ring are consistent with previously published structures, suggesting that the substitu-ents used have little effect towards destabilization of the ring.
Comment
The title compound, (I), has two molecules in the asymmetric unit and is composed of four rings; the sydnone ring, two phenyl rings and another ®ve-membered ring formed by a carbon bridge between the sydnone and attached phenyl ring (C6±C11). No signi®cant difference in bond lengths is observed between moleculeA, which, for the purpose of this determination, has anRcon®guration at C12a, and molecule
B, which has anScon®guration at C12b. The bond distances (Table 1) are statistically within the average found for the 24 structures determined in-house or cited in the Cambridge Structural Database (Allen, 2002). The bond angles within molecules AandBare similar to each other, however, when compared to other data, both molecules have slightly smaller N3ÐN2ÐO1 angles and slightly larger N2ÐN3ÐC4 angles. The average N3ÐN2ÐO1 angle of published data is 103.8 (2), while moleculesAandBhave angles of 102.05 (10)
and 101.68 (12), respectively. The average N2ÐN3ÐC4 angle
of published data is 115.7 (2), while moleculesAandBhave
angles of 117.14 (11) and 117.92 (12), respectively.
In (I), moleculeAhas a twist of 4.64 (7)between the plane
of the sydnone ring and the plane of the fused phenyl ring (C6a±C11a). The central ring (N3a/C4a/C6a/C7a/C12a) of the fused ring system is slightly offset from the sydnone ring by 1.49 (8). The isolated phenyl ring (C14a±C19a) is noticeably
bent at 51.34 (6)from the fused ring system. MoleculeBhas a
twist of 2.37 (12)between the plane of the sydnone ring and
the fused phenyl ring (C6b±C11b). The fused ring (N3b/C4b/ C6b/C7b/C12b) is offset from the sydnone ring by 2.07 (8).
The isolated phenyl ring (C14b±C19b) is again bent at 57.79 (5) from the plane of the fused ring system. Each
independent molecule forms a centrosymmetric OÐH O hydrogen-bonded pair. Details of the hydrogen-bonding geometries are given in Table 2.
Experimental
The title compound was made by treating 3-(2-bromophenyl)sydnone with n-butyllithium and reacting with ethyl phenylacetate, readily forming stable crystals (Krein, 1996).
Crystal data
C16H12N2O3 Mr= 280.28 Triclinic,P1
a= 9.502 (3) AÊ
b= 11.906 (3) AÊ
c= 13.676 (3) AÊ
= 105.712 (17)
= 108.29 (2)
= 101.13 (2) V= 1347.1 (7) AÊ3
Z= 4
Dx= 1.382 Mg mÿ3 MoKradiation Cell parameters from 6477
re¯ections
= 2.3±28.1
= 0.10 mmÿ1 T= 298 (2) K
Rectangular block, colorless 0.400.300.25 mm
Data collection
Bruker SMART APEX CCD diffractometer
!scans
Absorption correction: multi-scan (SADABSinSAINT-Plus; Bruker, 1997±1999)
Tmin= 0.901,Tmax= 0.976
11 422 measured re¯ections
6005 independent re¯ections 4886 re¯ections withI> 2(I)
Rint= 0.014
max= 28.2 h=ÿ12!12
k=ÿ15!15
l=ÿ17!18
Re®nement
Re®nement onF2 R[F2> 2(F2)] = 0.045 wR(F2) = 0.146 S= 1.06 6005 re¯ections 381 parameters
H-atom parameters constrained
w= 1/[2(F
o2) + (0.1P)2] whereP= (Fo2+ 2Fc2)/3 (/)max< 0.001
max= 0.28 e AÊÿ3
min=ÿ0.19 e AÊÿ3
Table 1
Selected geometric parameters (AÊ,).
O1aÐN2a 1.3835 (16)
O1aÐC5a 1.4098 (16)
O3aÐC12a 1.4124 (16)
N3aÐN2a 1.3000 (16)
N3aÐC4a 1.3435 (17)
N3aÐC6a 1.4305 (17)
O5aÐC5a 1.2214 (16)
C4aÐC5a 1.3962 (18)
C4aÐC12a 1.5147 (18)
C7aÐC8a 1.3813 (18)
C7aÐC6a 1.3873 (19)
C7aÐC12a 1.5284 (17)
C13aÐC12a 1.5500 (18)
C6aÐC11a 1.3712 (19)
C8aÐC9a 1.389 (2)
C11aÐC10a 1.385 (2)
C9aÐC10a 1.380 (2)
O1bÐN2b 1.3826 (18)
O1bÐC5b 1.425 (2)
O3bÐC12b 1.4224 (16)
N3bÐN2b 1.2994 (16)
N3bÐC4b 1.3313 (18)
N3bÐC6b 1.4282 (17)
O5bÐC5b 1.2179 (18)
C4bÐC5b 1.3995 (18)
C4bÐC12b 1.5092 (19)
C7bÐC8b 1.3767 (19)
C7bÐC6b 1.3821 (19)
C7bÐC12b 1.5290 (17)
C13bÐC12b 1.5402 (19)
C6bÐC11b 1.372 (2)
C8bÐC9b 1.385 (2)
C11bÐC10b 1.379 (2)
C9bÐC10b 1.385 (3)
N2aÐO1aÐC5a 111.76 (9) N2aÐN3aÐC4a 117.14 (11) N2aÐN3aÐC6a 130.36 (11) C4aÐN3aÐC6a 112.47 (11) N3aÐC4aÐC5a 105.29 (11) N3aÐC4aÐC12a 110.17 (11) C5aÐC4aÐC12a 144.44 (12) O5aÐC5aÐC4a 137.25 (12) O5aÐC5aÐO1a 119.01 (11) C4aÐC5aÐO1a 103.75 (11) C8aÐC7aÐC6a 118.16 (13) C8aÐC7aÐC12a 129.99 (12) C6aÐC7aÐC12a 111.84 (11) N3aÐN2aÐO1a 102.05 (10) O3aÐC12aÐC4a 110.28 (10) O3aÐC12aÐC7a 111.74 (10) C4aÐC12aÐC7a 99.50 (10) O3aÐC12aÐC13a 111.97 (10) C4aÐC12aÐC13a 111.31 (10) C7aÐC12aÐC13a 111.42 (10) C11aÐC6aÐC7a 125.12 (13) C11aÐC6aÐN3a 129.06 (13) C7aÐC6aÐN3a 105.75 (11) C7aÐC8aÐC9a 118.24 (15) C6aÐC11aÐC10a 115.44 (15) C10aÐC9aÐC8a 121.63 (14) C9aÐC10aÐC11a 121.40 (14)
N2bÐO1bÐC5b 111.80 (10) N2bÐN3bÐC4b 117.92 (12) N2bÐN3bÐC6b 129.62 (12) C4bÐN3bÐC6b 112.45 (11) N3bÐC4bÐC5b 105.60 (13) N3bÐC4bÐC12b 110.63 (11) C5bÐC4bÐC12b 143.64 (13) O5bÐC5bÐC4b 137.41 (16) O5bÐC5bÐO1b 119.61 (13) C4bÐC5bÐO1b 102.95 (12) C8bÐC7bÐC6b 118.48 (12) C8bÐC7bÐC12b 129.84 (12) C6bÐC7bÐC12b 111.67 (11) N3bÐN2bÐO1b 101.68 (12) O3bÐC12bÐC4b 114.01 (11) O3bÐC12bÐC7b 107.73 (10) C4bÐC12bÐC7b 99.37 (11) O3bÐC12bÐC13b 109.53 (11) C4bÐC12bÐC13b 112.89 (10) C7bÐC12bÐC13b 112.93 (11) C11bÐC6bÐC7b 124.48 (13) C11bÐC6bÐN3b 129.66 (13) C7bÐC6bÐN3b 105.86 (11) C7bÐC8bÐC9b 118.45 (14) C6bÐC11bÐC10b 116.18 (15) C10bÐC9bÐC8b 121.51 (14) C11bÐC10bÐC9b 120.89 (14)
organic papers
Acta Cryst.(2004). E60, o1568±o1570 Gordon B. Riddleet al. C16H12N2O3
o1569
Figure 1
MoleculeAof (I), shown with 30% probability displacement ellipsoids. H
Table 2
Hydrogen-bonding geometry (AÊ,).
DÐH a DÐH H A D A DÐH A
O3aÐH3a O5ai 0.82 1.91 2.7240 (18) 169
O3bÐH3b O5bii 0.82 1.90 2.7091 (19) 169
Symmetry codes: (i) 1ÿx;2ÿy;1ÿz; (ii) 2ÿx;2ÿy;ÿz.
All H atoms were placed in calculated positions, with OÐH = 0.82 AÊ, CÐHmethylene= 0.97 AÊ and CÐH = 0.93 AÊ for all others. They
were included in the re®nement in the riding-model approximation, with Uiso = 1.2Ueq[1.5Ueq(O)] of the carrier atom. The hydroxyl
H-atom position was calculated by generating a difference electron density map in a circle at the appropriate OÐH distance and CÐOÐ H angle. The point of maximum electron density was taken as the starting point for the H-atom position. The position was re-idealized at the beginning of each interation of least-squares re®nement.
Data collection: SMART (Bruker, 1997±2000); cell re®nement:
SAINT-Plus (Bruker, 1997±1999); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to re®ne structure:SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995); software used to prepare material for publication:OSCAIL(McArdle, 1995).
The authors acknowledge Allen Hunter for instrument time at Youngstown State University.
References
Allen, F. H. (2002)Acta Cryst.B58, 380±388.
Bruker (1997±2000).SMART for WNT/2000. Version 5.625. Bruker AXS Inc., Madison, Wisconsin, USA.
Bruker (1997±1999).SAINT-Plus.Version 6.02. Bruker AXS Inc., Madison, Wisconsin, USA.
Krein, D. M. (1996). MSs thesis, Wright State University, Dayton, Ohio, USA. McArdle, P. (1995).J. Appl. Cryst.28, 65.
Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of GoÈttingen, Germany.
organic papers
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Acta Cryst. (2004). E60, o1568–o1570
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Acta Cryst. (2004). E60, o1568–o1570 [https://doi.org/10.1107/S1600536804020082]
The sydnone compound 4-hydroxy-4-benzylsydno[3,4-
a
]indole
Gordon B. Riddle, David A. Grossie and Kenneth Turnbull
4-hydroxy-4-benzylsydno[3,4-a](4H)indole
Crystal data
C16H12N2O3
Mr = 280.28
Triclinic, P1 Hall symbol: -P 1 a = 9.502 (3) Å b = 11.906 (3) Å c = 13.676 (3) Å α = 105.712 (17)° β = 108.29 (2)° γ = 101.13 (2)° V = 1347.1 (7) Å3
Z = 4 F(000) = 584 Dx = 1.382 Mg m−3
Melting point: 426 K
Mo Kα radiation, λ = 0.71073 Å Cell parameters from 6477 reflections θ = 2.3–28.1°
µ = 0.10 mm−1
T = 298 K
Rectangular, colorless 0.40 × 0.30 × 0.25 mm
Data collection
Bruker AXS SMART APEX CCD diffractometer
Radiation source: fine-focus sealed tube Graphite monochromator
ω scans
Absorption correction: multi-scan
(SADABS in SAINT-Plus; Bruker, 1997-1999) Tmin = 0.901, Tmax = 0.976
11422 measured reflections 6005 independent reflections 4886 reflections with I > 2σ(I) Rint = 0.014
θmax = 28.2°, θmin = 1.7°
h = −12→12 k = −15→15 l = −17→18
Refinement
Refinement on F2
Least-squares matrix: full R[F2 > 2σ(F2)] = 0.045
wR(F2) = 0.146
S = 1.06 6005 reflections 381 parameters 0 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) + (0.1P)2]
where P = (Fo2 + 2Fc2)/3
(Δ/σ)max < 0.001
Δρmax = 0.28 e Å−3
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Acta Cryst. (2004). E60, o1568–o1570 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.
Mean-plane data from final SHELX refinement
run:-Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane) - 8.1127 (0.0046) x + 7.8485 (0.0066) y - 0.2533 (0.0094) z = 3.1676 (0.0041)
* 0.0038 (0.0010) C14A * 0.0010 (0.0011) C15A * -0.0046 (0.0012) C16A * 0.0033 (0.0013) C17A * 0.0016 (0.0012) C18A * -0.0051 (0.0011) C19A
Rms deviation of fitted atoms = 0.0035
- 2.6464 (0.0056) x + 10.8309 (0.0051) y + 2.0412 (0.0082) z = 10.1654 (0.0041) Angle to previous plane (with approximate e.s.d.) = 51.34 (0.06)
* -0.0122 (0.0007) N3A * -0.0104 (0.0007) C6A * 0.0256 (0.0008) C7A * -0.0296 (0.0007) C12A * 0.0266 (0.0007) C4A
Rms deviation of fitted atoms = 0.0224
- 2.4963 (0.0051) x + 11.1286 (0.0049) y + 1.1567 (0.0078) z = 9.9972 (0.0045) Angle to previous plane (with approximate e.s.d.) = 3.74 (0.07)
* 0.0051 (0.0009) C6A * -0.0063 (0.0009) C7A * 0.0011 (0.0010) C8A * 0.0055 (0.0010) C9A * -0.0069 (0.0010) C10A * 0.0015 (0.0010) C11A
Rms deviation of fitted atoms = 0.0050
- 2.8753 (0.0060) x + 10.7764 (0.0051) y + 2.2230 (0.0082) z = 10.1658 (0.0040) Angle to previous plane (with approximate e.s.d.) = 4.64 (0.07)
* 0.0024 (0.0007) O1A * 0.0000 (0.0007) N2A * -0.0026 (0.0008) N3A * 0.0038 (0.0007) C4A * -0.0037 (0.0007) C5A Rms deviation of fitted atoms = 0.0029
- 3.4270 (0.0061) x + 7.5076 (0.0061) y - 10.0366 (0.0072) z = 5.8654 (0.0058) Angle to previous plane (with approximate e.s.d.) = 72.28 (0.05)
* -0.0077 (0.0009) C14B * 0.0040 (0.0010) C15B * 0.0019 (0.0011) C16B * -0.0042 (0.0012) C17B * 0.0004 (0.0012) C18B * 0.0056 (0.0010) C19B
Rms deviation of fitted atoms = 0.0046
1.4271 (0.0056) x + 3.7764 (0.0069) y + 8.9339 (0.0072) z = 4.1664 (0.0060) Angle to previous plane (with approximate e.s.d.) = 57.79 (0.05)
* -0.0050 (0.0007) N3B * 0.0073 (0.0007) C6B * -0.0065 (0.0008) C7B * 0.0033 (0.0007) C12B * 0.0010 (0.0008) C4B Rms deviation of fitted atoms = 0.0051
1.3977 (0.0059) x + 3.9600 (0.0072) y + 8.8117 (0.0073) z = 4.2825 (0.0051) Angle to previous plane (with approximate e.s.d.) = 0.94 (0.11)
* -0.0053 (0.0009) C6B * 0.0018 (0.0009) C7B * 0.0031 (0.0010) C8B * -0.0045 (0.0012) C9B * 0.0011 (0.0012) C10B * 0.0038 (0.0011) C11B
Rms deviation of fitted atoms = 0.0036
1.7641 (0.0058) x + 3.6965 (0.0079) y + 8.7020 (0.0078) z = 4.3642 (0.0068) Angle to previous plane (with approximate e.s.d.) = 2.37 (0.12)
* 0.0095 (0.0008) O1B * -0.0036 (0.0007) N2B * -0.0042 (0.0008) N3B * 0.0095 (0.0007) C4B * -0.0112 (0.0008) C5B Rms deviation of fitted atoms = 0.0082
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
O1A 0.06381 (11) 0.91184 (9) 0.23631 (7) 0.0514 (3) O3A 0.38874 (11) 1.02465 (9) 0.58549 (8) 0.0510 (3)
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N3A 0.04449 (12) 0.87778 (9) 0.37416 (8) 0.0398 (2) O5A 0.32522 (12) 0.97072 (11) 0.28399 (8) 0.0571 (3) C14A 0.25884 (15) 0.68517 (12) 0.41996 (11) 0.0422 (3) C4A 0.19893 (14) 0.91401 (11) 0.40119 (10) 0.0390 (3) C5A 0.21751 (15) 0.93699 (12) 0.31043 (10) 0.0427 (3) C7A 0.14545 (15) 0.87376 (11) 0.54491 (10) 0.0409 (3) N2A −0.04404 (14) 0.87417 (12) 0.27835 (9) 0.0521 (3) C13A 0.36584 (15) 0.80779 (13) 0.50322 (11) 0.0456 (3)
H13A 0.4523 0.8328 0.4826 0.055*
H13B 0.4077 0.7999 0.5746 0.055*
C12A 0.28376 (14) 0.90847 (11) 0.51301 (10) 0.0397 (3) C6A 0.00500 (15) 0.85209 (11) 0.46019 (10) 0.0410 (3) C8A 0.14229 (18) 0.86358 (13) 0.64249 (12) 0.0521 (3)
H8A 0.2339 0.8782 0.7016 0.063*
C11A −0.13872 (17) 0.81907 (13) 0.46460 (13) 0.0514 (3)
H11A −0.2302 0.8050 0.4056 0.062*
C15A 0.17663 (18) 0.60081 (14) 0.44962 (13) 0.0545 (4)
H15A 0.1908 0.6181 0.5232 0.065*
C19A 0.23467 (19) 0.65548 (14) 0.30891 (12) 0.0540 (4)
H19A 0.2900 0.7106 0.2873 0.065*
C9A −0.0013 (2) 0.83097 (14) 0.65003 (13) 0.0583 (4)
H9A −0.0052 0.8243 0.7154 0.070*
C10A −0.1384 (2) 0.80816 (13) 0.56291 (14) 0.0584 (4)
H10A −0.2326 0.7850 0.5704 0.070*
C18A 0.1313 (2) 0.54699 (16) 0.23084 (14) 0.0675 (4)
H18A 0.1163 0.5295 0.1571 0.081*
C16A 0.0734 (2) 0.49084 (15) 0.37131 (18) 0.0713 (5)
H16A 0.0194 0.4346 0.3927 0.086*
C17A 0.0497 (2) 0.46379 (16) 0.26182 (17) 0.0726 (5)
H17A −0.0208 0.3901 0.2093 0.087*
N3B 0.78504 (12) 0.72564 (10) 0.03365 (8) 0.0442 (3) O3B 0.72381 (11) 0.99693 (9) 0.06274 (8) 0.0538 (3)
H3B 0.8027 1.0342 0.0588 0.081*
O1B 0.98113 (12) 0.72160 (11) −0.00281 (9) 0.0643 (3) C12B 0.67248 (14) 0.87303 (11) −0.00974 (10) 0.0407 (3) C7B 0.58262 (14) 0.79513 (11) 0.03645 (10) 0.0401 (3) C14B 0.52104 (15) 0.73598 (12) −0.21101 (10) 0.0418 (3) C13B 0.57398 (16) 0.86318 (12) −0.12691 (11) 0.0452 (3)
H13C 0.4833 0.8886 −0.1257 0.054*
H13D 0.6347 0.9192 −0.1492 0.054*
C6B 0.65269 (15) 0.70994 (12) 0.06281 (10) 0.0425 (3) O5B 0.99882 (13) 0.87069 (11) −0.07826 (10) 0.0713 (4) C4B 0.80143 (14) 0.81551 (12) −0.00627 (10) 0.0425 (3) C19B 0.61095 (17) 0.70102 (15) −0.26917 (11) 0.0531 (3)
H19B 0.7014 0.7580 −0.2587 0.064*
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Acta Cryst. (2004). E60, o1568–o1570
H8B 0.3995 0.8563 0.0388 0.061*
C15B 0.38509 (16) 0.64930 (14) −0.23059 (11) 0.0516 (3)
H15B 0.3216 0.6709 −0.1937 0.062*
C11B 0.59983 (19) 0.62972 (14) 0.10828 (12) 0.0567 (4)
H11B 0.6512 0.5744 0.1258 0.068*
C18B 0.5683 (2) 0.58295 (17) −0.34242 (13) 0.0652 (4)
H18B 0.6305 0.5608 −0.3802 0.078*
C16B 0.3427 (2) 0.53138 (15) −0.30412 (13) 0.0636 (4)
H16B 0.2515 0.4740 −0.3162 0.076*
C9B 0.3922 (2) 0.71922 (17) 0.10006 (14) 0.0620 (4)
H9B 0.3018 0.7210 0.1125 0.074*
C10B 0.4663 (2) 0.63578 (16) 0.12644 (14) 0.0647 (4)
H10B 0.4254 0.5831 0.1568 0.078*
C17B 0.4351 (2) 0.49881 (16) −0.35943 (14) 0.0678 (5)
H17B 0.4068 0.4192 −0.4086 0.081*
Atomic displacement parameters (Å2)
U11 U22 U33 U12 U13 U23
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sup-5
Acta Cryst. (2004). E60, o1568–o1570
O5B 0.0558 (6) 0.0720 (7) 0.0754 (8) −0.0002 (5) 0.0413 (6) 0.0054 (6) C4B 0.0377 (6) 0.0461 (7) 0.0354 (6) 0.0073 (5) 0.0119 (5) 0.0082 (5) C19B 0.0479 (8) 0.0660 (9) 0.0415 (7) 0.0131 (7) 0.0170 (6) 0.0164 (7) N2B 0.0555 (7) 0.0660 (8) 0.0615 (8) 0.0294 (6) 0.0210 (6) 0.0175 (6) C5B 0.0397 (7) 0.0520 (8) 0.0477 (8) 0.0043 (6) 0.0174 (6) −0.0018 (6) C8B 0.0495 (8) 0.0615 (9) 0.0521 (8) 0.0192 (7) 0.0278 (6) 0.0249 (7) C15B 0.0457 (7) 0.0630 (9) 0.0453 (7) 0.0133 (6) 0.0152 (6) 0.0232 (7) C11B 0.0684 (10) 0.0548 (8) 0.0510 (8) 0.0187 (7) 0.0228 (7) 0.0256 (7) C18B 0.0635 (10) 0.0788 (11) 0.0479 (8) 0.0311 (9) 0.0186 (7) 0.0115 (8) C16B 0.0580 (9) 0.0592 (9) 0.0552 (9) 0.0026 (7) 0.0071 (7) 0.0211 (7) C9B 0.0608 (9) 0.0759 (11) 0.0640 (9) 0.0182 (8) 0.0398 (8) 0.0304 (8) C10B 0.0752 (11) 0.0681 (10) 0.0630 (10) 0.0123 (8) 0.0385 (9) 0.0343 (8) C17B 0.0739 (11) 0.0567 (9) 0.0535 (9) 0.0210 (8) 0.0081 (8) 0.0095 (7)
Geometric parameters (Å, º)
O1A—N2A 1.3835 (16) N3B—N2B 1.2994 (16)
O1A—C5A 1.4098 (16) N3B—C4B 1.3313 (18)
O3A—C12A 1.4124 (16) N3B—C6B 1.4282 (17)
O3A—H3A 0.8200 O3B—C12B 1.4224 (16)
N3A—N2A 1.3000 (16) O3B—H3B 0.8200
N3A—C4A 1.3435 (17) O1B—N2B 1.3826 (18)
N3A—C6A 1.4305 (17) O1B—C5B 1.425 (2)
O5A—C5A 1.2214 (16) C12B—C4B 1.5092 (19)
C14A—C15A 1.3784 (19) C12B—C7B 1.5290 (17)
C14A—C19A 1.3940 (19) C12B—C13B 1.5402 (19)
C14A—C13A 1.504 (2) C7B—C8B 1.3767 (19)
C4A—C5A 1.3962 (18) C7B—C6B 1.3821 (19)
C4A—C12A 1.5147 (18) C14B—C19B 1.3858 (19)
C7A—C8A 1.3813 (18) C14B—C15B 1.387 (2)
C7A—C6A 1.3873 (19) C14B—C13B 1.5062 (19)
C7A—C12A 1.5284 (17) C13B—H13C 0.9700
C13A—C12A 1.5500 (18) C13B—H13D 0.9700
C13A—H13A 0.9700 C6B—C11B 1.372 (2)
C13A—H13B 0.9700 O5B—C5B 1.2179 (18)
C6A—C11A 1.3712 (19) C4B—C5B 1.3995 (18)
C8A—C9A 1.389 (2) C19B—C18B 1.381 (2)
C8A—H8A 0.9300 C19B—H19B 0.9300
C11A—C10A 1.385 (2) C8B—C9B 1.385 (2)
C11A—H11A 0.9300 C8B—H8B 0.9300
C15A—C16A 1.382 (2) C15B—C16B 1.381 (2)
C15A—H15A 0.9300 C15B—H15B 0.9300
C19A—C18A 1.370 (2) C11B—C10B 1.379 (2)
C19A—H19A 0.9300 C11B—H11B 0.9300
C9A—C10A 1.380 (2) C18B—C17B 1.363 (3)
C9A—H9A 0.9300 C18B—H18B 0.9300
C10A—H10A 0.9300 C16B—C17B 1.372 (3)
supporting information
sup-6
Acta Cryst. (2004). E60, o1568–o1570
C18A—H18A 0.9300 C9B—C10B 1.385 (3)
C16A—C17A 1.377 (3) C9B—H9B 0.9300
C16A—H16A 0.9300 C10B—H10B 0.9300
C17A—H17A 0.9300 C17B—H17B 0.9300
N2A···N3Bi 3.040 (2) H9A···O5Biv 2.711
H3A···O5Aii 1.914 H3B···O5Bv 1.899
O5A···H13Diii 2.612 O5B···H9Avi 2.711
N2A—O1A—C5A 111.76 (9) N2B—N3B—C4B 117.92 (12)
C12A—O3A—H3A 109.5 N2B—N3B—C6B 129.62 (12)
N2A—N3A—C4A 117.14 (11) C4B—N3B—C6B 112.45 (11)
N2A—N3A—C6A 130.36 (11) C12B—O3B—H3B 109.5
C4A—N3A—C6A 112.47 (11) N2B—O1B—C5B 111.80 (10)
C15A—C14A—C19A 117.82 (14) O3B—C12B—C4B 114.01 (11) C15A—C14A—C13A 121.47 (12) O3B—C12B—C7B 107.73 (10) C19A—C14A—C13A 120.66 (12) C4B—C12B—C7B 99.37 (11)
N3A—C4A—C5A 105.29 (11) O3B—C12B—C13B 109.53 (11)
N3A—C4A—C12A 110.17 (11) C4B—C12B—C13B 112.89 (10)
C5A—C4A—C12A 144.44 (12) C7B—C12B—C13B 112.93 (11)
O5A—C5A—C4A 137.25 (12) C8B—C7B—C6B 118.48 (12)
O5A—C5A—O1A 119.01 (11) C8B—C7B—C12B 129.84 (12)
C4A—C5A—O1A 103.75 (11) C6B—C7B—C12B 111.67 (11)
C8A—C7A—C6A 118.16 (13) C19B—C14B—C15B 117.84 (13)
C8A—C7A—C12A 129.99 (12) C19B—C14B—C13B 120.26 (12) C6A—C7A—C12A 111.84 (11) C15B—C14B—C13B 121.87 (12)
N3A—N2A—O1A 102.05 (10) C14B—C13B—C12B 113.42 (11)
C14A—C13A—C12A 112.91 (11) C14B—C13B—H13C 108.9
C14A—C13A—H13A 109.0 C12B—C13B—H13C 108.9
C12A—C13A—H13A 109.0 C14B—C13B—H13D 108.9
C14A—C13A—H13B 109.0 C12B—C13B—H13D 108.9
C12A—C13A—H13B 109.0 H13C—C13B—H13D 107.7
H13A—C13A—H13B 107.8 C11B—C6B—C7B 124.48 (13)
O3A—C12A—C4A 110.28 (10) C11B—C6B—N3B 129.66 (13)
O3A—C12A—C7A 111.74 (10) C7B—C6B—N3B 105.86 (11)
C4A—C12A—C7A 99.50 (10) N3B—C4B—C5B 105.60 (13)
O3A—C12A—C13A 111.97 (10) N3B—C4B—C12B 110.63 (11)
C4A—C12A—C13A 111.31 (10) C5B—C4B—C12B 143.64 (13)
C7A—C12A—C13A 111.42 (10) C18B—C19B—C14B 121.05 (14)
C11A—C6A—C7A 125.12 (13) C18B—C19B—H19B 119.5
C11A—C6A—N3A 129.06 (13) C14B—C19B—H19B 119.5
C7A—C6A—N3A 105.75 (11) N3B—N2B—O1B 101.68 (12)
C7A—C8A—C9A 118.24 (15) O5B—C5B—C4B 137.41 (16)
C7A—C8A—H8A 120.9 O5B—C5B—O1B 119.61 (13)
C9A—C8A—H8A 120.9 C4B—C5B—O1B 102.95 (12)
C6A—C11A—C10A 115.44 (15) C7B—C8B—C9B 118.45 (14)
C6A—C11A—H11A 122.3 C7B—C8B—H8B 120.8
supporting information
sup-7
Acta Cryst. (2004). E60, o1568–o1570
C14A—C15A—C16A 120.77 (15) C16B—C15B—C14B 120.89 (15)
C14A—C15A—H15A 119.6 C16B—C15B—H15B 119.6
C16A—C15A—H15A 119.6 C14B—C15B—H15B 119.6
C18A—C19A—C14A 121.61 (15) C6B—C11B—C10B 116.18 (15)
C18A—C19A—H19A 119.2 C6B—C11B—H11B 121.9
C14A—C19A—H19A 119.2 C10B—C11B—H11B 121.9
C10A—C9A—C8A 121.63 (14) C17B—C18B—C19B 120.11 (16)
C10A—C9A—H9A 119.2 C17B—C18B—H18B 119.9
C8A—C9A—H9A 119.2 C19B—C18B—H18B 119.9
C9A—C10A—C11A 121.40 (14) C17B—C16B—C15B 120.01 (16)
C9A—C10A—H10A 119.3 C17B—C16B—H16B 120.0
C11A—C10A—H10A 119.3 C15B—C16B—H16B 120.0
C19A—C18A—C17A 119.84 (16) C10B—C9B—C8B 121.51 (14)
C19A—C18A—H18A 120.1 C10B—C9B—H9B 119.2
C17A—C18A—H18A 120.1 C8B—C9B—H9B 119.2
C17A—C16A—C15A 120.56 (15) C11B—C10B—C9B 120.89 (14)
C17A—C16A—H16A 119.7 C11B—C10B—H10B 119.6
C15A—C16A—H16A 119.7 C9B—C10B—H10B 119.6
C16A—C17A—C18A 119.40 (17) C18B—C17B—C16B 120.08 (16)
C16A—C17A—H17A 120.3 C18B—C17B—H17B 120.0
C18A—C17A—H17A 120.3 C16B—C17B—H17B 120.0
supporting information
sup-8
Acta Cryst. (2004). E60, o1568–o1570
C6A—C7A—C12A—C13A −112.54 (12) O3B—C12B—C4B—C5B −70.9 (2) C14A—C13A—C12A—O3A −175.62 (10) C7B—C12B—C4B—C5B 174.83 (17) C14A—C13A—C12A—C4A −51.66 (14) C13B—C12B—C4B—C5B 54.9 (2) C14A—C13A—C12A—C7A 58.41 (14) C15B—C14B—C19B—C18B −1.4 (2) C8A—C7A—C6A—C11A −1.1 (2) C13B—C14B—C19B—C18B 176.63 (13) C12A—C7A—C6A—C11A 179.84 (12) C4B—N3B—N2B—O1B −0.13 (15) C8A—C7A—C6A—N3A 175.87 (11) C6B—N3B—N2B—O1B 178.60 (11) C12A—C7A—C6A—N3A −3.17 (14) C5B—O1B—N2B—N3B −1.20 (14) N2A—N3A—C6A—C11A −1.6 (2) N3B—C4B—C5B—O5B 176.36 (17) C4A—N3A—C6A—C11A 176.53 (12) C12B—C4B—C5B—O5B 1.2 (3) N2A—N3A—C6A—C7A −178.44 (12) N3B—C4B—C5B—O1B −1.90 (13) C4A—N3A—C6A—C7A −0.30 (14) C12B—C4B—C5B—O1B −177.01 (16) C6A—C7A—C8A—C9A 0.7 (2) N2B—O1B—C5B—O5B −176.66 (12) C12A—C7A—C8A—C9A 179.50 (12) N2B—O1B—C5B—C4B 1.98 (14) C7A—C6A—C11A—C10A 0.4 (2) C6B—C7B—C8B—C9B −0.1 (2) N3A—C6A—C11A—C10A −175.90 (12) C12B—C7B—C8B—C9B −179.02 (13) C19A—C14A—C15A—C16A −0.3 (2) C19B—C14B—C15B—C16B 1.3 (2) C13A—C14A—C15A—C16A 177.00 (13) C13B—C14B—C15B—C16B −176.75 (13) C15A—C14A—C19A—C18A 0.9 (2) C7B—C6B—C11B—C10B 0.9 (2) C13A—C14A—C19A—C18A −176.42 (14) N3B—C6B—C11B—C10B −179.50 (14) C7A—C8A—C9A—C10A 0.5 (2) C14B—C19B—C18B—C17B 0.7 (2) C8A—C9A—C10A—C11A −1.3 (2) C14B—C15B—C16B—C17B −0.4 (2) C6A—C11A—C10A—C9A 0.8 (2) C7B—C8B—C9B—C10B 0.7 (2) C14A—C19A—C18A—C17A −0.7 (3) C6B—C11B—C10B—C9B −0.3 (2) C14A—C15A—C16A—C17A −0.5 (3) C8B—C9B—C10B—C11B −0.5 (3) C15A—C16A—C17A—C18A 0.7 (3) C19B—C18B—C17B—C16B 0.3 (3) C19A—C18A—C17A—C16A −0.1 (3) C15B—C16B—C17B—C18B −0.4 (3)
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+2, −z+1; (iii) −x+1, −y+2, −z; (iv) x−1, y, z+1; (v) −x+2, −y+2, −z; (vi) x+1, y, z−1.
Hydrogen-bond geometry (Å, º)
D—H···A D—H H···A D···A D—H···A
O3A—H3A···O5Aii 0.82 1.91 2.7240 (18) 169
O3B—H3B···O5Bv 0.82 1.90 2.7091 (19) 169
