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Crystal structure determination of the title mol­ecule, C30H24N2O2S, reveals that the pyrrole ring in this fused heterocycle, although presumably strained and reactive in cyclo­addition reactions, does not differ appreciably from N-methyl­pyrrole except for a shorter C-C single bond [1.409 (4) Å] in the pyrrole ring.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100000020/fr1236sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270100000020/fr1236Isup2.hkl
Contains datablock I

CCDC reference: 144635

Comment top

Fused heterocycles such as the title compound, (I), are finding significant use as stable synthetic analogues of indole-2,3-quinodimethane for the construction of carbazoles and related natural products (Sha, 1996; Daly et al., 1997). In continuation of our interest in these ring systems (Pelkey & Gribble, 1997; Gribble et al., 1998), we needed to confirm the structure of the major product formed in the reaction between the mesoionic münchnone 3-benzyl-2-methyl-4-phenyl-1,3-oxazolium-5-olate and 3-nitro-1-(phenylsulfonyl)indole to give either 2-benzyl-3-methyl-1-phenyl-4-phenylsulfonyl-2H,4H-pyrrolo[3,4-b]indole, (I), or the isomeric 2-benzyl-1-methyl-3-phenyl-4phenylsulfonyl-2H,4H-pyrrolo[3,4-b]indole, in which the methyl and phenyl groups are interchanged. This novel chemistry has been published for symmetrical münchnones, which give unambiguous results (Gribble et al., 1998). \scheme

The crystal structure determination reported herein supports our tentative isomer assignment using NMR methods that (I) is the major product of this 1,3-dipolar cycloaddition reaction. The present paper appears to report the first crystal structure of the pyrrolo[3,4-b]indole ring system. The tricyclic fused ring system is essentially planar as anticipated. The dihedral angle of C1 to the phenyl ring, N2—C1—C11—C16, is 52.2 (4)°, unlike biphenyl which is coplanar (Trotter, 1961). The dihedral angle between the least squares planes of the N-benzyl phenyl ring, C17—C22, and the pyrrole ring is 96.9 (2)°, while that between the phenylsulfonyl ring, C26—C31, and the pyrrolindole ring system, C1/N2/C3/C3a/N4/C4a/C8a/C8b, is 60.3 (2)°. These conformations are more or less anticipated since π-conjugation between these phenyl rings and the pyrroloindole ring system is non-existent.

The pyrrole C=C double bonds [C1=C8b 1.378 (4) Å and C3=C3a 1.367 (4) Å] are slightly shorter than the comparable bond length in N-benzylisoindole (1.384 Å; Bonnett et al., 1985). Likewise, the pyrrole ring N—C single bonds [C1—N2 1.393 (4) Å and N2—C3 1.404 (3) Å] are slightly longer than the comparable bond in N-benzylisoindole (1.365 Å; Bonnett et al., 1985). This indicates that the pyrrole ring in (I) is more `pyrrole-like' and less delocalized than the pyrrole ring in N-benzylisoindole. For comparison, the C=C double bond in N-methylpyrrole is 1.35 Å and the N—C bond length is 1.40 Å, as determined by electron diffraction (Vilkov et al., 1962). The single bond between the two five-membered rings [C3a—C8b 1.409 (4) Å] is slightly compressed compared with the same (C3—C4) bond in N-methylpyrrole (1.43 Å) and N-benzylisoindole (1.429 Å), as a consequence of the two fused aromatic five-membered rings.

The mean deviation of the N-benzyl pyrrole nitrogen, N2, from the plane of its nearest three neighbours, C1, C3 and C9, is -0.082 (8) Å, while for the N-phenylsulfonyl nitrogen, N4, and its nearest three neighbours, C3a, C4a and S23, it is -0.437 (1) Å, making N4 significantly pyramidal. The internal bond angles in the N-benzylpyrrole ring are very similar to those reported for N-benzylisoindole.

In summary, the N-benzyl pyrrole ring, which is embedded in the highly congested title pyrroloindole, (I), is structurally similar to a normal pyrrole ring, although it is certainly more strained than a simple pyrrole by virtue of it being fused to another five-membered ring at the C3a—C8b positions.

Experimental top

Compound (I) was prepared by our general method from 3-nitro-1-phenylsulfonylindole and N-benzyl-N-benzoylalinine (Gribble et al., 1998) and recrystallized from dichloromethane to give colourless blocks (m.p. 444–445 K). The full synthetic details will be described separately.

Refinement top

Idealized C—H distances were in the range 0.95–0.97 Å.

Computing details top

Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1994); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1997-1999); program(s) used to solve structure: SIR93 (Altomare et al., 1993) and DIRDIF94 (Beurskens et al., 1994) Query; program(s) used to refine structure: SHELXL93 (Sheldrick, 1993); software used to prepare material for publication: TEXSAN for Windows.

Figures top
[Figure 1] Fig. 1. ORTEPII (Johnson 1976) diagram of (I) showing 30% probability displacement ellipsoids. H atoms are drawn as spheres of arbitrary radii.
(I) top
Crystal data top
C30H24N2O2SZ = 2
Mr = 476.59F(000) = 500.00
Triclinic, P1Dx = 1.293 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.7107 Å
a = 10.300 (1) ÅCell parameters from 20 reflections
b = 13.390 (1) Åθ = 6.2–7.6°
c = 9.322 (7) ŵ = 0.16 mm1
α = 105.65 (9)°T = 296 K
β = 98.62 (9)°Prism, light yellow
γ = 88.45 (3)°0.5 × 0.4 × 0.4 mm
V = 1223.9 (4) Å3
Data collection top
Rigaku AFC-6S
diffractometer
Rint = 0.026
Radiation source: X-ray tubeθmax = 27.5°, θmin = 1.6°
Graphite monochromatorh = 013
ω/2θ scansk = 1717
5951 measured reflectionsl = 1211
5637 independent reflections3 standard reflections every 150 reflections
2632 reflections with I > 3σ(I) intensity decay: 3.0%
Refinement top
Refinement on F0 constraints
Least-squares matrix: fullH-atom parameters not refined
R[F2 > 2σ(F2)] = 0.050Weighting scheme based on measured s.u.'s w = 1/[σ2(Fo) + 0.00004|Fo|2]
wR(F2) = 0.196(Δ/σ)max = 0.030
S = 2.34Δρmax = 0.30 e Å3
5637 reflectionsΔρmin = 0.36 e Å3
317 parametersExtinction correction: Zachariasen (1967), equ(3) Acta Cryst. (1968) A24, p213.
0 restraintsExtinction coefficient: 4.5 (2) × 10-6
Crystal data top
C30H24N2O2Sγ = 88.45 (3)°
Mr = 476.59V = 1223.9 (4) Å3
Triclinic, P1Z = 2
a = 10.300 (1) ÅMo Kα radiation
b = 13.390 (1) ŵ = 0.16 mm1
c = 9.322 (7) ÅT = 296 K
α = 105.65 (9)°0.5 × 0.4 × 0.4 mm
β = 98.62 (9)°
Data collection top
Rigaku AFC-6S
diffractometer
Rint = 0.026
5951 measured reflections3 standard reflections every 150 reflections
5637 independent reflections intensity decay: 3.0%
2632 reflections with I > 3σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0500 restraints
wR(F2) = 0.196H-atom parameters not refined
S = 2.34Δρmax = 0.30 e Å3
5637 reflectionsΔρmin = 0.36 e Å3
317 parameters
Special details top

Experimental. The scan width was (1.00 + 0.34tanθ)° with an ω scan speed of 8° per minute (up to 5 scans to achieve I/σ(I) > 10). Stationary background counts were recorded at each end of the scan, and the scan time:background time ratio was 2:1.

Refinement. The structure for C(30)H(24)N(2)SO(2) solved by direct methods (Altomare, A., Cascarano,M., Giacovazzo,C., Guagliardi, A., 1993) and expanded using Fourier techniques (Beurskens, P.T., Admiraal, G., Beurskens, G., Bosman, W.P., de Gelder, R., Israel, R. and Smits, J.M.M., 1994). The non-hydrogen atoms were refined anisotropically. Hydrogen atoms were included but not refined. The final cycle of full-matrix least-squares refinement (SHELXL93: Σw(Fo2-Fc2)2 where w = 1/ [ Σ2 (Fo2) + (0.1000 . P) 2 + 0.0000 . P ] and P = (Max(Fo2,0) + 2Fc2)/3)was based on 2632 observed reflections and 317, variable parameters and converged (largest parameter shift was 0.03 times its esd) with unweighted and weighted agreement factors of: R1 = Σ ||Fo| - |Fc|| / Σ |Fo| = 0.056; wR2 = [Σ(w (Fo2-Fc 2)2 )/Σ w(Fo2)2]1/2 = 0.209. The standard deviation of an observation of unit weight( [Σw(Fo2- Fc2)2/(No-Nv)]1/2 where No = number of observations and Nv = number of variables) was 1.12. The weighting scheme was based on counting statistics and included a factor (p = 0.013) to downweight the intense reflections. The maximum and minimum peaks in the final difference Fourier map corresponded to 0.58 and -0.72 e-/Å3, respectively.

Neutral atom scattering factors were taken from Cromer and Waber (Cromer, D. T. & Waber, J. T. (1974);. Anomalous dispersion effects were included in Fcalc (Ibers, J. A. & Hamilton, W. C., 1964); the values for δf' and δf" were those of Creagh and McAule (Creagh, D. C. & McAuley, W.J ., 1992). The values for the mass attenuation coefficients are those of Creagh and Hubbell (Creagh, D. C. & Hubbell, J.H., 1992). All calculations were performed using the teXsan (Molecular Structure Corporation, 1997-1998) crystallographic software package of Molecular Structure Corporation except for refinement, which was performed using SHELXL93 (Sheldrick, G.M., 1993).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S231.30359 (8)0.15538 (6)0.68662 (9)0.0488 (2)
O241.4195 (2)0.0976 (2)0.6582 (2)0.0695 (7)
O251.2628 (2)0.1753 (2)0.8309 (2)0.0699 (8)
N20.8527 (2)0.1973 (2)0.5723 (2)0.0432 (7)
N41.1803 (2)0.0905 (2)0.5609 (2)0.0419 (7)
C10.8730 (3)0.1813 (2)0.4234 (3)0.0384 (8)
C30.9639 (3)0.1708 (2)0.6607 (3)0.0416 (9)
C3a1.0526 (2)0.1385 (2)0.5629 (3)0.0392 (8)
C4a1.1996 (3)0.0668 (2)0.4036 (3)0.0410 (8)
C51.3044 (3)0.0160 (2)0.3404 (3)0.051 (1)
C61.3048 (3)0.0033 (2)0.1883 (4)0.055 (1)
C71.2027 (3)0.0387 (2)0.1003 (3)0.056 (1)
C81.0957 (3)0.0866 (2)0.1628 (3)0.0481 (9)
C8a1.0925 (2)0.1007 (2)0.3159 (3)0.0391 (8)
C8b0.9988 (2)0.1445 (2)0.4174 (3)0.0380 (8)
C90.7428 (3)0.2529 (2)0.6374 (3)0.051 (1)
C100.9674 (3)0.1810 (2)0.8235 (3)0.056 (1)
C110.7742 (3)0.2012 (2)0.3021 (3)0.0410 (8)
C120.8106 (3)0.2591 (2)0.2111 (3)0.0500 (9)
C130.7224 (3)0.2780 (2)0.0954 (3)0.061 (1)
C140.5962 (3)0.2413 (3)0.0683 (3)0.062 (1)
C150.5582 (3)0.1823 (3)0.1555 (4)0.065 (1)
C160.6467 (3)0.1606 (2)0.2708 (3)0.053 (1)
C170.7691 (3)0.3668 (3)0.7128 (3)0.056 (1)
C180.6744 (3)0.4242 (3)0.7903 (4)0.071 (1)
C190.6901 (5)0.5278 (4)0.8571 (5)0.101 (2)
C200.7992 (6)0.5769 (3)0.8517 (6)0.122 (2)
C210.8968 (5)0.5233 (4)0.7788 (6)0.125 (2)
C220.8810 (4)0.4168 (3)0.7064 (5)0.087 (1)
C261.3162 (3)0.2739 (2)0.6427 (3)0.0504 (9)
C271.2578 (3)0.3604 (3)0.7212 (4)0.081 (1)
C281.2670 (5)0.4533 (4)0.6810 (7)0.118 (2)
C291.3310 (5)0.4549 (4)0.5644 (8)0.123 (2)
C301.3876 (4)0.3694 (4)0.4868 (5)0.104 (2)
C311.3813 (3)0.2780 (3)0.5243 (4)0.067 (1)
H51.37380.00940.39990.061*
H61.37670.03050.14260.066*
H71.20630.03010.00350.066*
H81.02370.10980.10110.057*
H9a0.67030.24650.55920.061*
H9b0.72080.22100.71040.061*
H10a1.05420.20160.87400.067*
H10b0.90560.23170.86610.068*
H10c0.94830.11440.83560.067*
H120.89790.28640.22970.060*
H130.75010.31680.03260.072*
H140.53490.25650.00940.075*
H150.47080.15570.13650.078*
H160.62060.11760.32810.063*
H180.59710.38980.79730.086*
H190.62290.56510.90810.121*
H200.81010.64980.89660.144*
H210.97570.55790.77730.147*
H220.94750.38030.65390.104*
H271.21300.35750.80270.096*
H281.22780.51480.73470.139*
H291.33740.51860.53910.147*
H301.43140.37260.40460.124*
H311.42100.21740.46950.080*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S230.0415 (4)0.0604 (6)0.0429 (5)0.0048 (4)0.0047 (3)0.0177 (4)
O240.047 (1)0.082 (2)0.074 (2)0.019 (1)0.009 (1)0.021 (1)
O250.068 (1)0.102 (2)0.041 (1)0.005 (1)0.001 (1)0.026 (1)
N20.040 (1)0.045 (2)0.046 (1)0.002 (1)0.010 (1)0.013 (1)
N40.038 (1)0.045 (1)0.043 (1)0.003 (1)0.001 (1)0.014 (1)
C10.035 (2)0.040 (2)0.041 (2)0.002 (1)0.005 (1)0.012 (1)
C30.044 (2)0.044 (2)0.039 (2)0.001 (1)0.008 (1)0.014 (1)
C3a0.037 (2)0.040 (2)0.040 (2)0.000 (1)0.000 (1)0.014 (1)
C4a0.042 (2)0.035 (2)0.044 (2)0.001 (1)0.005 (1)0.007 (1)
C50.040 (2)0.049 (2)0.059 (2)0.006 (1)0.006 (2)0.008 (2)
C60.046 (2)0.053 (2)0.061 (2)0.005 (2)0.017 (2)0.001 (2)
C70.058 (2)0.062 (2)0.046 (2)0.002 (2)0.017 (2)0.008 (2)
C80.047 (2)0.054 (2)0.042 (2)0.001 (2)0.006 (1)0.013 (1)
C8a0.038 (2)0.037 (2)0.042 (2)0.001 (1)0.007 (1)0.010 (1)
C8b0.037 (2)0.038 (2)0.040 (2)0.000 (1)0.004 (1)0.013 (1)
C90.043 (2)0.057 (2)0.053 (2)0.006 (2)0.017 (1)0.011 (2)
C100.056 (2)0.070 (2)0.045 (2)0.000 (2)0.011 (2)0.019 (2)
C110.037 (2)0.040 (2)0.044 (2)0.006 (1)0.006 (1)0.011 (1)
C120.046 (2)0.049 (2)0.055 (2)0.001 (1)0.002 (2)0.018 (2)
C130.076 (2)0.058 (2)0.053 (2)0.013 (2)0.006 (2)0.024 (2)
C140.058 (2)0.065 (2)0.057 (2)0.017 (2)0.008 (2)0.013 (2)
C150.044 (2)0.075 (3)0.066 (2)0.001 (2)0.008 (2)0.010 (2)
C160.044 (2)0.059 (2)0.056 (2)0.003 (2)0.007 (2)0.016 (2)
C170.058 (2)0.059 (2)0.046 (2)0.009 (2)0.000 (2)0.013 (2)
C180.079 (3)0.075 (3)0.055 (2)0.028 (2)0.011 (2)0.012 (2)
C190.117 (4)0.082 (4)0.081 (3)0.035 (3)0.002 (3)0.008 (3)
C200.145 (5)0.058 (3)0.127 (4)0.021 (3)0.025 (4)0.008 (3)
C210.106 (4)0.061 (3)0.186 (6)0.019 (3)0.010 (4)0.011 (3)
C220.071 (3)0.062 (3)0.122 (4)0.001 (2)0.010 (2)0.014 (2)
C260.041 (2)0.054 (2)0.051 (2)0.006 (1)0.003 (1)0.009 (2)
C270.074 (3)0.061 (3)0.100 (3)0.002 (2)0.021 (2)0.005 (2)
C280.101 (4)0.056 (3)0.192 (6)0.004 (3)0.025 (4)0.022 (4)
C290.091 (4)0.089 (4)0.204 (7)0.019 (3)0.013 (4)0.083 (4)
C300.096 (3)0.121 (4)0.109 (4)0.036 (3)0.007 (3)0.065 (3)
C310.055 (2)0.080 (3)0.069 (2)0.015 (2)0.006 (2)0.025 (2)
Geometric parameters (Å, º) top
S23—O241.424 (2)C11—C161.394 (4)
S23—O251.424 (2)C12—C131.376 (4)
S23—N41.674 (2)C12—H120.95
S23—C261.755 (4)C13—C141.366 (5)
N2—C11.393 (4)C13—H130.96
N2—C31.404 (3)C14—C151.378 (5)
N2—C91.455 (4)C14—H140.95
N4—C3a1.449 (3)C15—C161.389 (4)
N4—C4a1.458 (4)C15—H150.95
C1—C8b1.378 (4)C16—H160.95
C1—C111.479 (4)C17—C181.390 (5)
C3—C3a1.367 (4)C17—C221.365 (5)
C3—C101.482 (4)C18—C191.361 (6)
C3a—C8b1.409 (4)C18—H180.95
C4a—C51.382 (4)C19—C201.332 (8)
C4a—C8a1.412 (4)C19—H190.95
C5—C61.382 (5)C20—C211.375 (8)
C5—H50.95C20—H200.95
C6—C71.388 (4)C21—C221.406 (6)
C6—H60.95C21—H210.95
C7—C81.385 (4)C22—H220.95
C7—H70.95C26—C271.370 (4)
C8—C8a1.393 (4)C26—C311.388 (5)
C8—H80.97C27—C281.402 (7)
C8a—C8b1.454 (4)C27—H270.96
C9—C171.510 (4)C28—C291.36 (1)
C9—H9a0.95C28—H280.95
C9—H9b0.95C29—C301.348 (7)
C10—H10b0.96C29—H290.95
C10—H10c0.97C30—C311.366 (7)
C10—H10a0.96C30—H300.96
C11—C121.388 (5)C31—H310.95
O24···C5i3.189 (3)C3···C4aii3.504 (4)
O24···C6i3.400 (4)
O24—S23—O25119.7 (1)C1—C11—C12119.1 (2)
O24—S23—N4106.6 (1)C1—C11—C16122.7 (3)
O24—S23—C26108.9 (1)C12—C11—C16118.1 (3)
O25—S23—N4106.9 (1)C11—C12—C13121.0 (3)
O25—S23—C26108.6 (1)C11—C12—H12119.3
N4—S23—C26105.2 (1)C13—C12—H12119.7
C1—N2—C3111.3 (2)C12—C13—C14120.7 (3)
C1—N2—C9125.2 (2)C12—C13—H13119.6
C3—N2—C9122.5 (2)C14—C13—H13119.7
S23—N4—C3a116.4 (2)C13—C14—C15119.4 (3)
S23—N4—C4a115.8 (2)C13—C14—H14120.5
C3a—N4—C4a104.0 (2)C15—C14—H14120.1
N2—C1—C8b106.0 (2)C14—C15—C16120.6 (3)
N2—C1—C11124.4 (2)C14—C15—H15119.9
C8b—C1—C11129.6 (3)C16—C15—H15119.5
N2—C3—C3a104.5 (2)C11—C16—C15120.1 (3)
N2—C3—C10121.8 (2)C11—C16—H16119.8
C3a—C3—C10133.7 (2)C15—C16—H16120.1
N4—C3a—C3138.7 (3)C9—C17—C18118.8 (3)
N4—C3a—C8b110.4 (2)C9—C17—C22122.9 (3)
C3—C3a—C8b110.5 (2)C18—C17—C22118.3 (3)
N4—C4a—C5127.2 (2)C17—C18—C19121.8 (4)
N4—C4a—C8a111.0 (2)C17—C18—H18118.9
C5—C4a—C8a121.8 (3)C19—C18—H18119.3
C4a—C5—C6117.9 (3)C18—C19—C20120.2 (4)
C4a—C5—H5120.8C18—C19—H19119.8
C6—C5—H5121.3C20—C19—H19119.9
C5—C6—C7121.6 (3)C19—C20—C21120.1 (4)
C5—C6—H6119.4C19—C20—H20120.7
C7—C6—H6119.1C21—C20—H20119.2
C6—C7—C8120.5 (3)C20—C21—C22120.4 (5)
C6—C7—H7119.8C20—C21—H21120.2
C8—C7—H7119.7C22—C21—H21119.4
C7—C8—C8a119.3 (3)C17—C22—C21119.1 (4)
C7—C8—H8120.5C17—C22—H22120.7
C8a—C8—H8120.2C21—C22—H22120.2
C4a—C8a—C8118.9 (2)S23—C26—C27120.0 (3)
C4a—C8a—C8b106.4 (2)S23—C26—C31119.4 (2)
C8—C8a—C8b134.7 (2)C27—C26—C31120.5 (3)
C1—C8b—C3a107.7 (2)C26—C27—C28118.6 (4)
C1—C8b—C8a143.8 (2)C26—C27—H27120.5
C3a—C8b—C8a108.1 (2)C28—C27—H27120.9
N2—C9—C17114.7 (2)C27—C28—C29119.5 (4)
N2—C9—H9a108.2C27—C28—H28120.2
N2—C9—H9b108.1C29—C28—H28120.3
C17—C9—H9a108.3C28—C29—C30121.7 (6)
C17—C9—H9b108.2C28—C29—H29118.6
H9a—C9—H9b109.2C30—C29—H29119.7
C3—C10—H10b111.4C29—C30—C31120.1 (5)
C3—C10—H10c108.3C29—C30—H30119.9
C3—C10—H10a108.6C31—C30—H30120.0
H10b—C10—H10c110.7C26—C31—C30119.5 (3)
H10b—C10—H10a109.5C26—C31—H31120.1
H10c—C10—H10a108.3C30—C31—H31120.3
S23—N4—C3a—C359.9 (4)C3a—N4—C4a—C5176.9 (3)
S23—N4—C3a—C8b128.0 (2)C3a—N4—C4a—C8a1.6 (3)
S23—N4—C4a—C554.0 (3)C3a—C3—N2—C9168.9 (2)
S23—N4—C4a—C8a127.4 (2)C3a—C8b—C1—C11179.6 (3)
S23—C26—C27—C28178.5 (3)C3a—C8b—C8a—C4a1.5 (3)
S23—C26—C31—C30177.9 (3)C3a—C8b—C8a—C8179.0 (3)
O24—S23—N4—C3a176.5 (2)C4a—N4—S23—C2661.7 (2)
O24—S23—N4—C4a53.8 (2)C4a—N4—C3a—C8b0.6 (3)
O24—S23—C26—C27148.4 (2)C4a—C5—C6—C71.0 (4)
O24—S23—C26—C3134.1 (3)C4a—C8a—C8—C70.7 (4)
O25—S23—N4—C3a54.3 (2)C5—C4a—C8a—C82.9 (4)
O25—S23—N4—C4a177.0 (2)C5—C4a—C8a—C8b176.7 (3)
O25—S23—C26—C2716.6 (3)C5—C6—C7—C81.1 (5)
O25—S23—C26—C31166.0 (2)C6—C5—C4a—C8a3.0 (4)
N2—C1—C8b—C3a0.2 (3)C6—C7—C8—C8a1.2 (5)
N2—C1—C8b—C8a171.9 (4)C7—C8—C8a—C8b178.7 (3)
N2—C1—C11—C12130.6 (3)C8a—C8b—C1—C117.8 (6)
N2—C1—C11—C1652.2 (4)C8b—C1—N2—C9168.4 (2)
N2—C3—C3a—N4172.1 (3)C8b—C1—C11—C1249.7 (4)
N2—C3—C3a—C8b0.0 (3)C8b—C1—C11—C16127.5 (3)
N2—C9—C17—C18174.1 (3)C8b—C3a—C3—C10179.8 (3)
N2—C9—C17—C227.0 (5)C9—N2—C1—C1111.8 (4)
N4—S23—C26—C2797.6 (2)C9—N2—C3—C1010.9 (4)
N4—S23—C26—C3179.9 (2)C9—C17—C18—C19178.1 (3)
N4—C3a—C3—C108.1 (6)C9—C17—C22—C21179.4 (4)
N4—C3a—C8b—C1174.3 (2)C11—C12—C13—C140.8 (4)
N4—C3a—C8b—C8a0.6 (3)C11—C16—C15—C141.9 (4)
N4—C4a—C5—C6178.6 (3)C12—C11—C16—C152.9 (4)
N4—C4a—C8a—C8178.5 (2)C12—C13—C14—C151.8 (5)
N4—C4a—C8a—C8b2.0 (3)C13—C12—C11—C161.6 (4)
C1—N2—C3—C3a0.1 (3)C13—C14—C15—C160.4 (5)
C1—N2—C3—C10179.9 (2)C17—C18—C19—C201.1 (7)
C1—N2—C9—C1793.2 (3)C17—C22—C21—C201.8 (7)
C1—C8b—C3a—C30.1 (3)C18—C17—C22—C210.6 (6)
C1—C8b—C8a—C4a170.2 (4)C18—C19—C20—C210.1 (8)
C1—C8b—C8a—C89.2 (6)C19—C18—C17—C220.9 (6)
C1—C11—C12—C13178.9 (2)C19—C20—C21—C221.5 (8)
C1—C11—C16—C15179.8 (3)C26—C27—C28—C291.2 (6)
C3—N2—C1—C8b0.2 (3)C26—C31—C30—C290.0 (6)
C3—N2—C1—C11179.6 (2)C27—C26—C31—C300.5 (5)
C3—N2—C9—C1774.2 (4)C27—C28—C29—C300.8 (8)
C3—C3a—N4—C4a171.5 (3)C28—C27—C26—C311.0 (5)
C3—C3a—C8b—C8a175.0 (2)C28—C29—C30—C310.2 (7)
C3a—N4—S23—C2661.0 (2)
Symmetry codes: (i) x+3, y, z+1; (ii) x+2, y, z+1.

Experimental details

Crystal data
Chemical formulaC30H24N2O2S
Mr476.59
Crystal system, space groupTriclinic, P1
Temperature (K)296
a, b, c (Å)10.300 (1), 13.390 (1), 9.322 (7)
α, β, γ (°)105.65 (9), 98.62 (9), 88.45 (3)
V3)1223.9 (4)
Z2
Radiation typeMo Kα
µ (mm1)0.16
Crystal size (mm)0.5 × 0.4 × 0.4
Data collection
DiffractometerRigaku AFC-6S
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 3σ(I)] reflections
5951, 5637, 2632
Rint0.026
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.050, 0.196, 2.34
No. of reflections5637
No. of parameters317
H-atom treatmentH-atom parameters not refined
Δρmax, Δρmin (e Å3)0.30, 0.36

Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1994), MSC/AFC Diffractometer Control Software, TEXSAN for Windows (Molecular Structure Corporation, 1997-1999), SIR93 (Altomare et al., 1993) and DIRDIF94 (Beurskens et al., 1994) Query, SHELXL93 (Sheldrick, 1993), TEXSAN for Windows.

Selected geometric parameters (Å, º) top
S23—N41.674 (2)C1—C8b1.378 (4)
N2—C11.393 (4)C3—C3a1.367 (4)
N2—C31.404 (3)C3a—C8b1.409 (4)
N2—C91.455 (4)C4a—C8a1.412 (4)
N4—C3a1.449 (3)C8a—C8b1.454 (4)
N4—C4a1.458 (4)
C1—N2—C3111.3 (2)S23—N4—C3a116.4 (2)
C1—N2—C9125.2 (2)S23—N4—C4a115.8 (2)
C3—N2—C9122.5 (2)C3a—N4—C4a104.0 (2)
 

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