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Acta Crystallogr Sect E Struct Rep Online. 2010 May 1; 66(Pt 5): o1019.
Published online 2010 April 2. doi:  10.1107/S160053681001175X
PMCID: PMC2979192

1-Benzyl-3-[(dimethyl­amino)methyl­ene]-4-phenyl-1H-1,5-benzodiazepine-2(3H)-thione

Abstract

The title compound, C25H23N3S, crystallizes with two independent mol­ecules in the asymmetric unit. The seven-membered fused-ring adopts a boat conformation, with the two bridgehead C atoms representing the stern and the C atom bearing the exocyclic double bond the prow.

Related literature

For background to the synthesis and biological activity of pyrazolo[4,3-c]triazolo[4,3-a][1,5] benzodiazepines, see: Ahab­chane et al. (2001 [triangle]).

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Object name is e-66-o1019-scheme1.jpg

Experimental

Crystal data

  • C25H23N3S
  • M r = 397.52
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1019-efi1.jpg
  • a = 26.4740 (8) Å
  • b = 10.2366 (2) Å
  • c = 16.5650 (5) Å
  • β = 106.136 (1)°
  • V = 4312.3 (2) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.17 mm−1
  • T = 293 K
  • 0.38 × 0.35 × 0.28 mm

Data collection

  • Bruker X8 APEX2 diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.940, T max = 0.955
  • 34616 measured reflections
  • 7429 independent reflections
  • 5019 reflections with I > 2σ(I)
  • R int = 0.047

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.150
  • S = 1.03
  • 7429 reflections
  • 527 parameters
  • H-atom parameters constrained
  • Δρmax = 0.19 e Å−3
  • Δρmin = −0.28 e Å−3

Data collection: APEX2 (Bruker, 2008 [triangle]); cell refinement: SAINT (Bruker, 2008 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: X-SEED (Barbour, 2001 [triangle]); software used to prepare material for publication: publCIF (Westrip, 2010 [triangle]).

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681001175X/bt5234sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053681001175X/bt5234Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

We thank Université Mohammed V-Agdal and the University of Malaya for supporting this study.

supplementary crystallographic information

Comment

The background to the class of precusor compounds is explained in a report on the syntheses and biological properties of pyrazolo[4,3-c]triazolo[4,3-a][1,5] benzodiazepines (Ahabchane et al., 2001). The methylene linkage of the seven-membered fused ring of 1-benzyl-4-phenyl-1,5-benzodiazepine-2-thione is exceptionally reactive; in the present study, this portion reacts with N,N-dimethylformamide–dimethylacetal to furnish a double bond.

The seven-membered fused-ring in C25H23N3S (Scheme I, Figs. 1 & 2) adopts a boat conformation (with the two phenylene carbons representing the stern and the carbon atom bearing the exocyclic double-bond the prow) in the two independent molecules. The fused-ring features exocyclic double (C═C and C═S) bonds on adjacent carbon occupants but the C(═C)–C(═S) fragment is twisted [-34.8 (3), 40.1 (3) °].

Experimental

1-Benzyl-4-phenyl-1,5-benzodiazepine-2-thione (1 g) and an excess of N,N-dimethylformamide dimethylacetal (DMF–DMA, 2.5 ml) were heated for 12 hours. The solid that formed upon cooling the mixture was recrystallized from ethanol to afford colorless crystals in 65% yield.

Refinement

H-atoms were placed in calculated positions (C—H 0.93–0.97 Å) and were included in the refinement in the riding model approximation, with U(H) set to 1.2U(C).

Figures

Fig. 1.
Anisotropic displacement ellipsoid plot (Barbour, 2001) of one independent molecule of C25H23N3S at the 50% probability level; hydrogen atoms are drawn as arbitrary radius.
Fig. 2.
Anisotropic displacement ellipsoid plot (Barbour, 2001) of the second independent molecule of C25H23N3S at the 50% probability level; hydrogen atoms are drawn as arbitrary radius.

Crystal data

C25H23N3SF(000) = 1680
Mr = 397.52Dx = 1.225 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 7420 reflections
a = 26.4740 (8) Åθ = 2.6–21.9°
b = 10.2366 (2) ŵ = 0.17 mm1
c = 16.5650 (5) ÅT = 293 K
β = 106.136 (1)°Block, colorless
V = 4312.3 (2) Å30.38 × 0.35 × 0.28 mm
Z = 8

Data collection

Bruker X8 APEX2 diffractometer7429 independent reflections
Radiation source: fine-focus sealed tube5019 reflections with I > 2σ(I)
graphiteRint = 0.047
[var phi] and ω scansθmax = 24.8°, θmin = 0.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −31→31
Tmin = 0.940, Tmax = 0.955k = −8→12
34616 measured reflectionsl = −19→19

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150H-atom parameters constrained
S = 1.03w = 1/[σ2(Fo2) + (0.0771P)2 + 0.7415P] where P = (Fo2 + 2Fc2)/3
7429 reflections(Δ/σ)max = 0.001
527 parametersΔρmax = 0.19 e Å3
0 restraintsΔρmin = −0.28 e Å3

Special details

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
S10.68147 (3)0.23703 (6)0.88424 (4)0.0681 (2)
S20.82290 (3)0.28053 (7)0.73502 (5)0.0811 (3)
N10.66628 (8)0.46928 (18)0.94582 (11)0.0537 (5)
N20.60213 (7)0.65564 (19)0.83124 (12)0.0503 (5)
N30.66494 (8)0.48619 (18)0.65939 (11)0.0507 (5)
N40.81709 (7)0.52681 (18)0.78290 (12)0.0505 (5)
N50.89168 (7)0.6994 (2)0.73201 (12)0.0553 (5)
N60.84302 (8)0.48869 (18)0.51100 (12)0.0540 (5)
C10.66570 (9)0.3953 (2)0.87702 (14)0.0457 (5)
C20.68024 (9)0.6051 (2)0.94640 (14)0.0474 (6)
C30.72558 (11)0.6494 (3)1.00447 (15)0.0646 (7)
H30.74600.59141.04330.078*
C40.74049 (11)0.7774 (3)1.00508 (18)0.0726 (8)
H40.77100.80591.04420.087*
C50.71064 (12)0.8640 (3)0.94813 (18)0.0670 (7)
H50.72140.95040.94740.080*
C60.66488 (10)0.8226 (2)0.89239 (15)0.0563 (6)
H60.64390.88250.85580.068*
C70.64933 (9)0.6922 (2)0.88965 (14)0.0460 (5)
C80.60280 (8)0.5527 (2)0.78745 (14)0.0457 (5)
C90.64898 (8)0.4652 (2)0.79744 (13)0.0423 (5)
C100.66833 (13)0.4077 (3)1.02656 (16)0.0730 (8)
H10A0.70370.41681.06360.088*
H10B0.66140.31501.01730.088*
C110.63036 (11)0.4626 (2)1.06983 (15)0.0565 (6)
C120.63693 (12)0.4266 (3)1.15333 (15)0.0678 (8)
H120.66570.37591.18090.081*
C130.60148 (15)0.4651 (3)1.1952 (2)0.0844 (10)
H130.60580.43861.25040.101*
C140.55973 (16)0.5424 (3)1.1560 (2)0.0943 (11)
H140.53590.56911.18460.113*
C150.55316 (14)0.5804 (3)1.0742 (2)0.0948 (10)
H150.52500.63381.04760.114*
C160.58831 (12)0.5394 (3)1.03122 (18)0.0753 (8)
H160.58330.56430.97560.090*
C170.55336 (9)0.5137 (3)0.72353 (15)0.0566 (6)
C180.51377 (10)0.6058 (3)0.69462 (18)0.0767 (8)
H180.51790.69030.71610.092*
C190.46822 (13)0.5715 (5)0.6338 (2)0.1040 (12)
H190.44180.63310.61440.125*
C200.46198 (15)0.4468 (6)0.6023 (2)0.1212 (17)
H200.43150.42450.56090.145*
C210.50005 (15)0.3556 (4)0.6313 (2)0.1088 (13)
H210.49520.27070.61060.131*
C220.54606 (11)0.3887 (3)0.69144 (18)0.0759 (8)
H220.57220.32630.71030.091*
C230.67079 (9)0.4318 (2)0.73465 (13)0.0453 (5)
H230.69320.36000.74610.054*
C240.63639 (10)0.6057 (3)0.63075 (16)0.0633 (7)
H24A0.63590.65870.67830.095*
H24B0.60100.58500.59960.095*
H24C0.65330.65260.59530.095*
C250.69212 (14)0.4298 (3)0.60257 (19)0.0846 (10)
H25A0.70990.35140.62690.127*
H25B0.71730.49130.59330.127*
H25C0.66710.40930.54990.127*
C260.82869 (9)0.4423 (2)0.72705 (15)0.0511 (6)
C270.80627 (9)0.6622 (2)0.76243 (13)0.0459 (5)
C280.75899 (9)0.7160 (2)0.76785 (15)0.0537 (6)
H280.73470.66330.78370.064*
C290.74769 (10)0.8452 (3)0.75021 (15)0.0603 (7)
H290.71570.87920.75320.072*
C300.78350 (11)0.9250 (2)0.72817 (15)0.0593 (7)
H300.77591.01290.71660.071*
C310.83043 (10)0.8741 (2)0.72333 (15)0.0571 (6)
H310.85470.92890.70930.068*
C320.84279 (9)0.7420 (2)0.73898 (14)0.0488 (6)
C330.89356 (9)0.5921 (2)0.69224 (14)0.0492 (6)
C340.84874 (9)0.5015 (2)0.66108 (14)0.0459 (5)
C350.80751 (10)0.4803 (3)0.86157 (15)0.0629 (7)
H35A0.79610.39000.85420.076*
H35B0.77900.53100.87210.076*
C360.85436 (11)0.4894 (2)0.93730 (15)0.0566 (6)
C370.85080 (14)0.4299 (3)1.01068 (17)0.0754 (8)
H370.82010.38611.01110.091*
C380.89202 (18)0.4346 (4)1.0831 (2)0.0983 (11)
H380.88940.39181.13120.118*
C390.93670 (18)0.5021 (4)1.0842 (2)0.1075 (13)
H390.96420.50621.13330.129*
C400.94095 (15)0.5642 (4)1.0124 (2)0.1018 (11)
H400.97120.61081.01310.122*
C410.89962 (12)0.5567 (3)0.93863 (18)0.0741 (8)
H410.90270.59750.89010.089*
C420.94507 (10)0.5544 (3)0.68004 (15)0.0612 (7)
C430.98279 (10)0.6497 (3)0.68304 (18)0.0791 (9)
H430.97600.73590.69440.095*
C441.03046 (13)0.6171 (5)0.6692 (2)0.1057 (13)
H441.05570.68130.67180.127*
C451.04039 (14)0.4910 (6)0.6519 (2)0.1153 (15)
H451.07220.46980.64170.138*
C461.00412 (15)0.3958 (4)0.6495 (2)0.1076 (13)
H461.01140.30990.63850.129*
C470.95619 (12)0.4269 (3)0.6635 (2)0.0807 (9)
H470.93150.36170.66180.097*
C480.83331 (9)0.4494 (2)0.58218 (15)0.0497 (6)
H480.81280.37460.57710.060*
C490.86997 (11)0.6091 (3)0.50126 (17)0.0675 (7)
H49A0.86680.67090.54320.101*
H49B0.85440.64480.44640.101*
H49C0.90650.59100.50780.101*
C500.82724 (13)0.4069 (3)0.43621 (17)0.0795 (9)
H50A0.80160.34450.44260.119*
H50B0.85740.36170.42880.119*
H50C0.81240.46060.38790.119*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.0990 (6)0.0484 (4)0.0570 (4)0.0109 (3)0.0218 (4)0.0068 (3)
S20.1156 (7)0.0479 (4)0.0950 (6)0.0057 (4)0.0544 (5)0.0176 (4)
N10.0777 (14)0.0499 (12)0.0360 (10)0.0084 (10)0.0200 (10)0.0073 (9)
N20.0505 (12)0.0540 (12)0.0469 (11)0.0068 (9)0.0140 (9)0.0049 (10)
N30.0650 (13)0.0514 (12)0.0384 (11)−0.0074 (10)0.0190 (9)−0.0014 (9)
N40.0601 (12)0.0521 (12)0.0428 (11)−0.0041 (9)0.0201 (9)0.0067 (9)
N50.0469 (12)0.0668 (14)0.0522 (12)−0.0125 (10)0.0137 (9)−0.0001 (10)
N60.0661 (13)0.0537 (12)0.0442 (11)−0.0009 (10)0.0188 (10)0.0026 (9)
C10.0470 (13)0.0487 (14)0.0415 (13)−0.0003 (10)0.0124 (10)0.0045 (10)
C20.0578 (14)0.0514 (14)0.0355 (12)0.0063 (11)0.0170 (11)−0.0035 (10)
C30.0728 (18)0.0748 (19)0.0413 (14)0.0154 (14)0.0078 (13)−0.0114 (13)
C40.0693 (18)0.084 (2)0.0619 (18)−0.0082 (16)0.0130 (15)−0.0288 (16)
C50.0786 (19)0.0661 (18)0.0637 (17)−0.0133 (15)0.0322 (16)−0.0191 (15)
C60.0731 (17)0.0503 (15)0.0528 (15)0.0058 (13)0.0299 (14)−0.0002 (12)
C70.0508 (14)0.0508 (14)0.0406 (12)0.0040 (11)0.0197 (11)−0.0010 (10)
C80.0440 (13)0.0563 (15)0.0373 (12)−0.0018 (10)0.0119 (10)0.0091 (11)
C90.0462 (13)0.0430 (12)0.0369 (12)−0.0046 (10)0.0103 (10)0.0000 (9)
C100.111 (2)0.0674 (17)0.0441 (15)0.0195 (16)0.0280 (15)0.0180 (13)
C110.0801 (18)0.0498 (14)0.0432 (14)−0.0087 (13)0.0230 (13)0.0008 (11)
C120.104 (2)0.0582 (16)0.0448 (15)−0.0079 (14)0.0270 (15)−0.0002 (12)
C130.135 (3)0.073 (2)0.0582 (18)−0.016 (2)0.047 (2)−0.0024 (15)
C140.126 (3)0.092 (2)0.090 (3)−0.006 (2)0.071 (2)0.002 (2)
C150.093 (2)0.109 (3)0.096 (3)0.0123 (19)0.049 (2)0.023 (2)
C160.083 (2)0.094 (2)0.0553 (17)0.0005 (17)0.0297 (16)0.0145 (15)
C170.0455 (14)0.0812 (19)0.0427 (13)−0.0084 (13)0.0117 (11)0.0102 (13)
C180.0481 (16)0.115 (2)0.0646 (18)0.0049 (16)0.0111 (14)0.0197 (16)
C190.053 (2)0.179 (4)0.073 (2)−0.001 (2)0.0064 (17)0.027 (3)
C200.064 (2)0.223 (5)0.065 (2)−0.050 (3)−0.0010 (19)0.010 (3)
C210.086 (3)0.152 (4)0.080 (2)−0.062 (3)0.009 (2)−0.017 (2)
C220.0687 (19)0.090 (2)0.0650 (18)−0.0293 (16)0.0116 (15)−0.0051 (16)
C230.0532 (14)0.0384 (12)0.0424 (13)−0.0068 (10)0.0104 (11)−0.0029 (10)
C240.0687 (17)0.0696 (17)0.0533 (15)0.0031 (13)0.0199 (13)0.0191 (13)
C250.138 (3)0.0695 (19)0.0611 (18)0.0058 (18)0.0527 (19)−0.0032 (14)
C260.0494 (14)0.0507 (14)0.0538 (14)0.0007 (11)0.0153 (11)0.0104 (11)
C270.0538 (14)0.0475 (14)0.0360 (12)−0.0107 (11)0.0116 (10)−0.0044 (10)
C280.0549 (15)0.0589 (16)0.0514 (14)−0.0091 (12)0.0215 (12)−0.0048 (12)
C290.0670 (17)0.0583 (17)0.0571 (16)0.0022 (13)0.0200 (13)−0.0092 (13)
C300.0779 (19)0.0493 (14)0.0479 (14)−0.0014 (13)0.0130 (13)−0.0060 (11)
C310.0679 (17)0.0529 (16)0.0482 (14)−0.0193 (13)0.0126 (12)−0.0032 (11)
C320.0516 (14)0.0545 (15)0.0387 (12)−0.0125 (11)0.0099 (11)−0.0041 (10)
C330.0459 (14)0.0597 (16)0.0422 (13)−0.0026 (11)0.0123 (11)0.0111 (11)
C340.0485 (13)0.0441 (13)0.0472 (13)0.0018 (10)0.0165 (11)0.0057 (10)
C350.0753 (18)0.0688 (17)0.0516 (15)−0.0050 (13)0.0290 (14)0.0135 (12)
C360.0785 (18)0.0496 (14)0.0451 (14)0.0119 (13)0.0225 (13)0.0030 (11)
C370.118 (3)0.0643 (17)0.0503 (17)0.0153 (16)0.0335 (17)0.0036 (13)
C380.149 (4)0.092 (3)0.0510 (19)0.028 (2)0.023 (2)0.0039 (17)
C390.130 (3)0.121 (3)0.054 (2)0.034 (3)−0.004 (2)−0.002 (2)
C400.090 (2)0.121 (3)0.082 (3)0.007 (2)0.002 (2)−0.002 (2)
C410.074 (2)0.089 (2)0.0551 (17)0.0070 (16)0.0124 (15)0.0074 (15)
C420.0475 (15)0.089 (2)0.0473 (14)0.0042 (14)0.0142 (12)0.0129 (13)
C430.0509 (16)0.121 (3)0.0668 (18)−0.0120 (16)0.0186 (14)0.0005 (17)
C440.054 (2)0.182 (4)0.084 (2)−0.012 (2)0.0234 (18)0.011 (3)
C450.057 (2)0.205 (5)0.089 (3)0.034 (3)0.0286 (19)0.028 (3)
C460.086 (3)0.142 (3)0.104 (3)0.053 (2)0.042 (2)0.038 (2)
C470.0653 (19)0.092 (2)0.088 (2)0.0247 (16)0.0270 (17)0.0269 (18)
C480.0523 (14)0.0441 (13)0.0548 (15)0.0024 (10)0.0185 (12)0.0046 (11)
C490.0755 (18)0.0737 (18)0.0563 (16)−0.0098 (14)0.0232 (14)0.0123 (13)
C500.109 (2)0.0770 (19)0.0531 (17)−0.0052 (17)0.0239 (16)−0.0049 (14)

Geometric parameters (Å, °)

S1—C11.669 (2)C21—H210.9300
S2—C261.672 (2)C22—H220.9300
N1—C11.365 (3)C23—H230.9300
N1—C21.438 (3)C24—H24A0.9600
N1—C101.466 (3)C24—H24B0.9600
N2—C81.283 (3)C24—H24C0.9600
N2—C71.402 (3)C25—H25A0.9600
N3—C231.334 (3)C25—H25B0.9600
N3—C241.447 (3)C25—H25C0.9600
N3—C251.454 (3)C26—C341.472 (3)
N4—C261.362 (3)C27—C281.393 (3)
N4—C271.437 (3)C27—C321.400 (3)
N4—C351.474 (3)C28—C291.370 (3)
N5—C331.289 (3)C28—H280.9300
N5—C321.400 (3)C29—C301.375 (3)
N6—C481.336 (3)C29—H290.9300
N6—C491.455 (3)C30—C311.370 (4)
N6—C501.457 (3)C30—H300.9300
C1—C91.457 (3)C31—C321.399 (3)
C2—C71.386 (3)C31—H310.9300
C2—C31.389 (3)C33—C421.484 (3)
C3—C41.368 (4)C33—C341.481 (3)
C3—H30.9300C34—C481.365 (3)
C4—C51.374 (4)C35—C361.502 (3)
C4—H40.9300C35—H35A0.9700
C5—C61.370 (4)C35—H35B0.9700
C5—H50.9300C36—C411.377 (4)
C6—C71.394 (3)C36—C371.386 (3)
C6—H60.9300C37—C381.380 (5)
C8—C91.487 (3)C37—H370.9300
C8—C171.491 (3)C38—C391.365 (5)
C9—C231.366 (3)C38—H380.9300
C10—C111.497 (4)C39—C401.381 (5)
C10—H10A0.9700C39—H390.9300
C10—H10B0.9700C40—C411.397 (4)
C11—C161.368 (4)C40—H400.9300
C11—C121.395 (3)C41—H410.9300
C12—C131.370 (4)C42—C471.382 (4)
C12—H120.9300C42—C431.387 (4)
C13—C141.367 (5)C43—C441.384 (4)
C13—H130.9300C43—H430.9300
C14—C151.374 (5)C44—C451.364 (6)
C14—H140.9300C44—H440.9300
C15—C161.384 (4)C45—C461.361 (6)
C15—H150.9300C45—H450.9300
C16—H160.9300C46—C471.388 (4)
C17—C221.378 (4)C46—H460.9300
C17—C181.392 (4)C47—H470.9300
C18—C191.384 (4)C48—H480.9300
C18—H180.9300C49—H49A0.9600
C19—C201.371 (6)C49—H49B0.9600
C19—H190.9300C49—H49C0.9600
C20—C211.360 (6)C50—H50A0.9600
C20—H200.9300C50—H50B0.9600
C21—C221.384 (4)C50—H50C0.9600
C1—N1—C2119.02 (18)H24B—C24—H24C109.5
C1—N1—C10120.81 (19)N3—C25—H25A109.5
C2—N1—C10117.75 (19)N3—C25—H25B109.5
C8—N2—C7117.40 (19)H25A—C25—H25B109.5
C23—N3—C24125.0 (2)N3—C25—H25C109.5
C23—N3—C25119.3 (2)H25A—C25—H25C109.5
C24—N3—C25115.5 (2)H25B—C25—H25C109.5
C26—N4—C27121.32 (18)N4—C26—C34116.01 (19)
C26—N4—C35121.48 (19)N4—C26—S2122.16 (17)
C27—N4—C35116.62 (19)C34—C26—S2121.78 (18)
C33—N5—C32118.36 (19)C28—C27—C32119.3 (2)
C48—N6—C49125.0 (2)C28—C27—N4119.3 (2)
C48—N6—C50119.8 (2)C32—C27—N4121.3 (2)
C49—N6—C50115.2 (2)C29—C28—C27121.0 (2)
N1—C1—C9114.40 (19)C29—C28—H28119.5
N1—C1—S1122.29 (17)C27—C28—H28119.5
C9—C1—S1123.29 (17)C28—C29—C30120.3 (2)
C7—C2—C3119.6 (2)C28—C29—H29119.9
C7—C2—N1121.0 (2)C30—C29—H29119.9
C3—C2—N1119.4 (2)C31—C30—C29119.5 (2)
C4—C3—C2120.6 (3)C31—C30—H30120.2
C4—C3—H3119.7C29—C30—H30120.2
C2—C3—H3119.7C30—C31—C32121.7 (2)
C3—C4—C5120.2 (3)C30—C31—H31119.1
C3—C4—H4119.9C32—C31—H31119.1
C5—C4—H4119.9N5—C32—C31117.3 (2)
C6—C5—C4119.7 (3)N5—C32—C27124.5 (2)
C6—C5—H5120.2C31—C32—C27118.1 (2)
C4—C5—H5120.2N5—C33—C42117.3 (2)
C5—C6—C7121.1 (2)N5—C33—C34124.8 (2)
C5—C6—H6119.5C42—C33—C34117.9 (2)
C7—C6—H6119.5C48—C34—C26118.4 (2)
C2—C7—C6118.7 (2)C48—C34—C33125.2 (2)
C2—C7—N2122.8 (2)C26—C34—C33114.7 (2)
C6—C7—N2118.5 (2)N4—C35—C36114.4 (2)
N2—C8—C9124.9 (2)N4—C35—H35A108.7
N2—C8—C17118.3 (2)C36—C35—H35A108.7
C9—C8—C17116.8 (2)N4—C35—H35B108.7
C23—C9—C1118.7 (2)C36—C35—H35B108.7
C23—C9—C8125.1 (2)H35A—C35—H35B107.6
C1—C9—C8115.48 (18)C41—C36—C37118.5 (3)
N1—C10—C11114.6 (2)C41—C36—C35123.8 (2)
N1—C10—H10A108.6C37—C36—C35117.6 (3)
C11—C10—H10A108.6C38—C37—C36121.1 (3)
N1—C10—H10B108.6C38—C37—H37119.4
C11—C10—H10B108.6C36—C37—H37119.4
H10A—C10—H10B107.6C39—C38—C37120.2 (3)
C16—C11—C12118.4 (3)C39—C38—H38119.9
C16—C11—C10124.0 (2)C37—C38—H38119.9
C12—C11—C10117.4 (2)C38—C39—C40119.9 (4)
C13—C12—C11120.8 (3)C38—C39—H39120.0
C13—C12—H12119.6C40—C39—H39120.0
C11—C12—H12119.6C39—C40—C41119.8 (4)
C14—C13—C12120.2 (3)C39—C40—H40120.1
C14—C13—H13119.9C41—C40—H40120.1
C12—C13—H13119.9C36—C41—C40120.5 (3)
C13—C14—C15119.7 (3)C36—C41—H41119.7
C13—C14—H14120.1C40—C41—H41119.7
C15—C14—H14120.1C47—C42—C43118.7 (3)
C14—C15—C16120.1 (3)C47—C42—C33121.8 (2)
C14—C15—H15119.9C43—C42—C33119.5 (3)
C16—C15—H15119.9C44—C43—C42120.3 (3)
C11—C16—C15120.7 (3)C44—C43—H43119.8
C11—C16—H16119.7C42—C43—H43119.8
C15—C16—H16119.7C45—C44—C43120.0 (4)
C22—C17—C18119.0 (3)C45—C44—H44120.0
C22—C17—C8121.6 (2)C43—C44—H44120.0
C18—C17—C8119.4 (3)C46—C45—C44120.5 (4)
C19—C18—C17119.9 (3)C46—C45—H45119.7
C19—C18—H18120.0C44—C45—H45119.7
C17—C18—H18120.0C45—C46—C47120.1 (4)
C20—C19—C18120.1 (4)C45—C46—H46120.0
C20—C19—H19120.0C47—C46—H46120.0
C18—C19—H19120.0C42—C47—C46120.3 (3)
C21—C20—C19120.4 (4)C42—C47—H47119.9
C21—C20—H20119.8C46—C47—H47119.9
C19—C20—H20119.8N6—C48—C34130.4 (2)
C20—C21—C22120.2 (4)N6—C48—H48114.8
C20—C21—H21119.9C34—C48—H48114.8
C22—C21—H21119.9N6—C49—H49A109.5
C17—C22—C21120.4 (3)N6—C49—H49B109.5
C17—C22—H22119.8H49A—C49—H49B109.5
C21—C22—H22119.8N6—C49—H49C109.5
N3—C23—C9130.0 (2)H49A—C49—H49C109.5
N3—C23—H23115.0H49B—C49—H49C109.5
C9—C23—H23115.0N6—C50—H50A109.5
N3—C24—H24A109.5N6—C50—H50B109.5
N3—C24—H24B109.5H50A—C50—H50B109.5
H24A—C24—H24B109.5N6—C50—H50C109.5
N3—C24—H24C109.5H50A—C50—H50C109.5
H24A—C24—H24C109.5H50B—C50—H50C109.5
C2—N1—C1—C9−34.4 (3)C27—N4—C26—C3422.1 (3)
C10—N1—C1—C9163.6 (2)C35—N4—C26—C34−166.9 (2)
C2—N1—C1—S1147.05 (18)C27—N4—C26—S2−160.33 (17)
C10—N1—C1—S1−14.9 (3)C35—N4—C26—S210.6 (3)
C1—N1—C2—C764.1 (3)C26—N4—C27—C28124.0 (2)
C10—N1—C2—C7−133.4 (2)C35—N4—C27—C28−47.4 (3)
C1—N1—C2—C3−115.5 (2)C26—N4—C27—C32−57.5 (3)
C10—N1—C2—C347.0 (3)C35—N4—C27—C32131.1 (2)
C7—C2—C3—C4−1.3 (4)C32—C27—C28—C290.3 (3)
N1—C2—C3—C4178.4 (2)N4—C27—C28—C29178.9 (2)
C2—C3—C4—C50.1 (4)C27—C28—C29—C30−1.2 (4)
C3—C4—C5—C62.1 (4)C28—C29—C30—C310.5 (4)
C4—C5—C6—C7−3.2 (4)C29—C30—C31—C321.0 (4)
C3—C2—C7—C60.2 (3)C33—N5—C32—C31−134.9 (2)
N1—C2—C7—C6−179.43 (19)C33—N5—C32—C2746.8 (3)
C3—C2—C7—N2−177.7 (2)C30—C31—C32—N5179.7 (2)
N1—C2—C7—N22.7 (3)C30—C31—C32—C27−1.8 (3)
C5—C6—C7—C22.0 (3)C28—C27—C32—N5179.5 (2)
C5—C6—C7—N2−180.0 (2)N4—C27—C32—N51.0 (3)
C8—N2—C7—C2−48.7 (3)C28—C27—C32—C311.1 (3)
C8—N2—C7—C6133.4 (2)N4—C27—C32—C31−177.4 (2)
C7—N2—C8—C93.7 (3)C32—N5—C33—C42175.4 (2)
C7—N2—C8—C17−178.59 (19)C32—N5—C33—C34−7.2 (3)
N1—C1—C9—C23146.7 (2)N4—C26—C34—C48−142.3 (2)
S1—C1—C9—C23−34.8 (3)S2—C26—C34—C4840.1 (3)
N1—C1—C9—C8−43.1 (3)N4—C26—C34—C3351.5 (3)
S1—C1—C9—C8135.43 (19)S2—C26—C34—C33−126.0 (2)
N2—C8—C9—C23−124.8 (2)N5—C33—C34—C48132.1 (3)
C17—C8—C9—C2357.4 (3)C42—C33—C34—C48−50.5 (3)
N2—C8—C9—C165.6 (3)N5—C33—C34—C26−62.9 (3)
C17—C8—C9—C1−112.1 (2)C42—C33—C34—C26114.5 (2)
C1—N1—C10—C11−133.9 (2)C26—N4—C35—C3697.5 (3)
C2—N1—C10—C1163.9 (3)C27—N4—C35—C36−91.2 (3)
N1—C10—C11—C1615.8 (4)N4—C35—C36—C4111.7 (4)
N1—C10—C11—C12−168.0 (2)N4—C35—C36—C37−170.6 (2)
C16—C11—C12—C131.3 (4)C41—C36—C37—C38−1.7 (4)
C10—C11—C12—C13−175.1 (3)C35—C36—C37—C38−179.5 (3)
C11—C12—C13—C14−1.6 (5)C36—C37—C38—C392.1 (5)
C12—C13—C14—C150.6 (5)C37—C38—C39—C40−0.9 (6)
C13—C14—C15—C160.8 (6)C38—C39—C40—C41−0.5 (6)
C12—C11—C16—C150.1 (4)C37—C36—C41—C400.2 (4)
C10—C11—C16—C15176.3 (3)C35—C36—C41—C40177.9 (3)
C14—C15—C16—C11−1.1 (5)C39—C40—C41—C360.9 (5)
N2—C8—C17—C22−161.3 (2)N5—C33—C42—C47159.0 (2)
C9—C8—C17—C2216.6 (3)C34—C33—C42—C47−18.6 (3)
N2—C8—C17—C1819.5 (3)N5—C33—C42—C43−22.7 (3)
C9—C8—C17—C18−162.6 (2)C34—C33—C42—C43159.7 (2)
C22—C17—C18—C19−0.7 (4)C47—C42—C43—C440.3 (4)
C8—C17—C18—C19178.5 (2)C33—C42—C43—C44−178.0 (3)
C17—C18—C19—C200.2 (5)C42—C43—C44—C450.5 (5)
C18—C19—C20—C210.9 (6)C43—C44—C45—C46−1.2 (6)
C19—C20—C21—C22−1.6 (6)C44—C45—C46—C471.0 (6)
C18—C17—C22—C210.1 (4)C43—C42—C47—C46−0.6 (4)
C8—C17—C22—C21−179.1 (3)C33—C42—C47—C46177.8 (3)
C20—C21—C22—C171.1 (5)C45—C46—C47—C42−0.1 (5)
C24—N3—C23—C96.3 (4)C49—N6—C48—C34−6.0 (4)
C25—N3—C23—C9−178.8 (2)C50—N6—C48—C34172.6 (3)
C1—C9—C23—N3−174.8 (2)C26—C34—C48—N6175.5 (2)
C8—C9—C23—N315.9 (4)C33—C34—C48—N6−20.0 (4)

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT5234).

References

  • Ahabchane, N. H., Ibrahimi, S., Salem, M., Essassi, E. M., Amzazi, S. & Benjouad, A. (2001). C. R. Acad. Sci. Paris Chim 4, 917–924.
  • Barbour, L. J. (2001). J. Supramol. Chem.1, 189–191.
  • Bruker (2008). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Westrip, S. P. (2010). publCIF In preparation.

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