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8b,8c-Di­phenyl-2,6-bis­(4-pyridyl­meth­yl)­perhydro-2,3a,4a,6,7a,8a-hexa­aza­cyclo­penta­[def]fluorene-4,8-di­thione chloro­form solvate

aKey Laboratory of Pesticides and Chemical Biology of the Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China
*Correspondence e-mail: net_dcong@163.com

(Received 27 April 2010; accepted 27 May 2010; online 5 June 2010)

In the thio­glycoluril system of the title compound, C32H30N8S2·CHCl3, the two pyridine rings are roughly parallel, forming a dihedral angle of 7.2 (1)°, and the distance between the centroids of the two phenyl rings is 3.951 (5) Å. The chloro­form solvent mol­ecule is linked to the main mol­ecule via a weak C—H⋯N hydrogen bond.

Related literature

For applications of glycoluril derivatives, see: Rowan et al. (1999[Rowan, A. E., Elemans, J. A. A. W. & Nolte, R. J. M. (1999). Acc. Chem. Res. 32, 995-1006.]). For the preparation of the title compound, see: Broan et al. (1989[Broan, C. J., Butler, A. R., Reed, D. & Sadler, I. H. (1989). J. Chem. Soc. Perkin Trans. 2, pp. 731-740.]); Li et al. (2008[Li, Y. T., Meng, X. G., Cao, L. P., Wang, Y. Z., Yin, G. D., Gao, M., Wen, L. L. & Wu, A. X. (2008). Cryst. Growth Des. 8, 1645-1653.]).

[Scheme 1]

Experimental

Crystal data
  • C32H30N8S2·CHCl3

  • Mr = 710.13

  • Triclinic, [P \overline 1]

  • a = 9.5381 (6) Å

  • b = 12.1712 (8) Å

  • c = 14.8765 (9) Å

  • α = 100.978 (1)°

  • β = 91.699 (1)°

  • γ = 98.500 (1)°

  • V = 1673.81 (18) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.44 mm−1

  • T = 294 K

  • 0.20 × 0.10 × 0.10 mm

Data collection
  • Bruker SMART APEX CCD area-detector diffractometer

  • 11061 measured reflections

  • 5690 independent reflections

  • 2136 reflections with I > 2σ(I)

  • Rint = 0.109

Refinement
  • R[F2 > 2σ(F2)] = 0.062

  • wR(F2) = 0.210

  • S = 0.85

  • 5690 reflections

  • 415 parameters

  • H-atom parameters constrained

  • Δρmax = 0.47 e Å−3

  • Δρmin = −0.39 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C33—H33⋯N8i 0.98 2.33 3.168 (9) 142 (8)
Symmetry code: (i) -x+2, -y+1, -z+1.

Data collection: SMART (Bruker, 1997[Bruker (1997). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 1999[Bruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Recently, molecular clips based on concave glycoluril unit have been widely investigated in supramolecular chemistry (Rowan et al., 1999). We report here the structure of the title compound (Fig. 1), which is a derivative of thioglycoluril with two pyridine units. We believe the title compound would offer the possibility in construction of coordination framework with novel patterns (Li et al., 2008). The crystal packing exhibits weak intermolecular C—H···N hydrogen bond (Table 1) between the chloroform solvent molecule and the main molecule.

Related literature top

For applications of glycoluril derivatives, see: Rowan et al. (1999). For the preparation of the title compound, see: Broan et al. (1989); Li et al. (2008).

Experimental top

The title compound was synthesized according to the literature (Broan et al., 1989; Li et al., 2008). Crystals of (I) suitable for X-ray diffraction were grown by slow evaporation of a chloroform-methanol (1:2) solution of the title compound under 293 K.

Refinement top

All H atoms were positioned in geometrically idealized positions and constrained to ride on their parent atoms, with C—H distances in the range 0.93-0.98 Å and Uiso(H) = 1.2-1.5Ueq(C). The low ratio observed/unique reflections (0.38) was mainly caused by poor quality of the crystal selected for measurements.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of (I), showing the atom-labelling scheme, with displacement ellipsoids drawn at the 30% probability level.
8b,8c-Diphenyl-2,6-bis(4-pyridylmethyl)perhydro-2,3a,4a,6,7a,8a- hexaazacyclopenta[def]fluorene-4,8-dithione chloroform solvate top
Crystal data top
C32H30N8S2·CHCl3V = 1673.81 (18) Å3
Mr = 710.13Z = 2
Triclinic, P1F(000) = 736
Hall symbol: -P 1Dx = 1.409 Mg m3
a = 9.5381 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.1712 (8) ŵ = 0.44 mm1
c = 14.8765 (9) ÅT = 294 K
α = 100.978 (1)°Block, colourless
β = 91.699 (1)°0.20 × 0.10 × 0.10 mm
γ = 98.500 (1)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2136 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.109
Graphite monochromatorθmax = 25.0°, θmin = 1.7°
phi and ω scansh = 1111
11061 measured reflectionsk = 1413
5690 independent reflectionsl = 1717
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.210H-atom parameters constrained
S = 0.85 w = 1/[σ2(Fo2) + (0.1041P)2]
where P = (Fo2 + 2Fc2)/3
5690 reflections(Δ/σ)max = 0.001
415 parametersΔρmax = 0.47 e Å3
0 restraintsΔρmin = 0.39 e Å3
Crystal data top
C32H30N8S2·CHCl3γ = 98.500 (1)°
Mr = 710.13V = 1673.81 (18) Å3
Triclinic, P1Z = 2
a = 9.5381 (6) ÅMo Kα radiation
b = 12.1712 (8) ŵ = 0.44 mm1
c = 14.8765 (9) ÅT = 294 K
α = 100.978 (1)°0.20 × 0.10 × 0.10 mm
β = 91.699 (1)°
Data collection top
Bruker SMART APEX CCD area-detector
diffractometer
2136 reflections with I > 2σ(I)
11061 measured reflectionsRint = 0.109
5690 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0620 restraints
wR(F2) = 0.210H-atom parameters constrained
S = 0.85Δρmax = 0.47 e Å3
5690 reflectionsΔρmin = 0.39 e Å3
415 parameters
Special details top

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.

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. Because of the poor quality of crystal, the ratio of Observed/Unique Reflections is 38%.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.4638 (5)0.4696 (4)0.1361 (4)0.0426 (14)
H1A0.40560.45150.07900.051*
H1B0.44860.54350.16850.051*
C20.6423 (6)0.3623 (4)0.0735 (4)0.0461 (15)
H2A0.74340.36590.06580.055*
H2B0.59340.33850.01330.055*
C30.4314 (5)0.4077 (4)0.2860 (4)0.0395 (14)
C40.6795 (5)0.2382 (4)0.1877 (4)0.0391 (14)
C50.4489 (5)0.2700 (4)0.1553 (3)0.0295 (12)
C60.3463 (5)0.2069 (4)0.0750 (3)0.0344 (13)
C70.3908 (6)0.1281 (5)0.0063 (4)0.0518 (16)
H70.48680.12220.00400.062*
C80.2952 (6)0.0585 (5)0.0584 (4)0.0565 (17)
H80.32620.00450.10310.068*
C90.1541 (7)0.0688 (5)0.0572 (4)0.0590 (17)
H90.08950.02230.10140.071*
C100.1082 (6)0.1478 (5)0.0096 (4)0.0546 (16)
H100.01250.15510.01040.065*
C110.2042 (6)0.2160 (4)0.0753 (4)0.0436 (15)
H110.17250.26900.12050.052*
C120.4498 (5)0.2132 (4)0.2406 (3)0.0322 (13)
C130.3367 (5)0.1100 (4)0.2397 (3)0.0351 (13)
C140.2062 (6)0.1236 (5)0.2759 (4)0.0567 (17)
H140.18770.19540.30200.068*
C150.1037 (7)0.0290 (6)0.2726 (4)0.0675 (19)
H150.01670.03760.29750.081*
C160.1289 (7)0.0762 (6)0.2335 (5)0.077 (2)
H160.05880.13890.23040.093*
C170.2577 (7)0.0896 (5)0.1986 (5)0.072 (2)
H170.27650.16140.17300.086*
C180.3601 (6)0.0048 (5)0.2017 (4)0.0570 (17)
H180.44700.00450.17700.068*
C190.4813 (6)0.2929 (4)0.4068 (3)0.0455 (15)
H19A0.47830.36210.45110.055*
H19B0.41620.23270.42450.055*
C200.6388 (6)0.1716 (4)0.3368 (4)0.0469 (15)
H20A0.58370.10330.34970.056*
H20B0.73760.16110.33640.056*
C210.7120 (6)0.5325 (5)0.1933 (4)0.0530 (16)
H21A0.71300.48390.23790.064*
H21B0.67860.60120.22270.064*
C220.8592 (6)0.5619 (4)0.1653 (4)0.0482 (16)
C230.8900 (6)0.6050 (5)0.0882 (4)0.0577 (17)
H230.81570.61570.05050.069*
C241.0254 (7)0.6325 (5)0.0652 (5)0.068 (2)
H241.04000.66190.01240.081*
C251.1118 (7)0.5806 (6)0.1887 (5)0.073 (2)
H251.18820.57300.22610.088*
C260.9754 (8)0.5499 (6)0.2152 (5)0.075 (2)
H260.96350.52040.26820.090*
C270.7389 (6)0.3621 (5)0.4180 (4)0.0481 (15)
H27A0.71050.42750.45700.058*
H27B0.75540.38040.35820.058*
C280.8721 (5)0.3375 (4)0.4579 (4)0.0384 (14)
C291.0046 (6)0.3720 (4)0.4278 (4)0.0505 (16)
H291.01260.40870.37840.061*
C301.1231 (6)0.3516 (5)0.4715 (5)0.0576 (18)
H301.20980.37610.44910.069*
C310.9976 (8)0.2679 (6)0.5694 (5)0.084 (2)
H310.99270.23110.61890.101*
C320.8720 (7)0.2838 (6)0.5309 (5)0.0676 (19)
H320.78650.25820.55420.081*
C330.6754 (7)0.8554 (6)0.3853 (5)0.076 (2)
H330.69490.78390.40010.091*
Cl10.7802 (3)0.9693 (2)0.4618 (2)0.1451 (11)
Cl20.4992 (2)0.86364 (19)0.39764 (19)0.1222 (10)
Cl30.7234 (2)0.86119 (18)0.27531 (15)0.1061 (8)
N10.4182 (4)0.3843 (3)0.1924 (3)0.0370 (11)
N20.5961 (4)0.2785 (3)0.1304 (3)0.0380 (12)
N30.4351 (4)0.3080 (3)0.3151 (3)0.0349 (11)
N40.5925 (4)0.1866 (3)0.2456 (3)0.0342 (11)
N50.6126 (5)0.4746 (4)0.1154 (3)0.0446 (12)
N61.1383 (6)0.6195 (4)0.1144 (5)0.0697 (17)
N70.6238 (4)0.2652 (3)0.4087 (3)0.0388 (11)
N81.1278 (6)0.3010 (5)0.5420 (5)0.0756 (17)
S10.85378 (14)0.24229 (12)0.18583 (10)0.0545 (5)
S20.43168 (16)0.53272 (12)0.35358 (10)0.0527 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.042 (3)0.042 (3)0.044 (3)0.002 (3)0.006 (3)0.013 (3)
C20.042 (3)0.056 (4)0.040 (3)0.002 (3)0.015 (3)0.009 (3)
C30.026 (3)0.050 (4)0.046 (4)0.009 (3)0.014 (3)0.012 (3)
C40.038 (3)0.028 (3)0.046 (3)0.004 (3)0.014 (3)0.006 (2)
C50.025 (3)0.032 (3)0.031 (3)0.006 (2)0.004 (2)0.003 (2)
C60.039 (3)0.032 (3)0.032 (3)0.001 (2)0.010 (3)0.006 (2)
C70.039 (3)0.055 (4)0.052 (4)0.002 (3)0.013 (3)0.009 (3)
C80.047 (4)0.063 (4)0.047 (4)0.000 (3)0.006 (3)0.012 (3)
C90.061 (4)0.058 (4)0.046 (4)0.009 (3)0.003 (3)0.005 (3)
C100.034 (3)0.055 (4)0.072 (5)0.003 (3)0.002 (3)0.014 (3)
C110.042 (3)0.040 (3)0.046 (4)0.002 (3)0.014 (3)0.005 (3)
C120.026 (3)0.032 (3)0.037 (3)0.001 (2)0.007 (2)0.005 (2)
C130.035 (3)0.038 (3)0.034 (3)0.002 (3)0.000 (3)0.015 (2)
C140.050 (4)0.060 (4)0.054 (4)0.006 (3)0.018 (3)0.007 (3)
C150.046 (4)0.090 (5)0.058 (4)0.019 (4)0.009 (3)0.013 (4)
C160.066 (5)0.066 (5)0.091 (5)0.026 (4)0.008 (4)0.020 (4)
C170.066 (5)0.038 (4)0.104 (6)0.006 (3)0.002 (4)0.007 (4)
C180.044 (4)0.039 (4)0.083 (5)0.007 (3)0.009 (3)0.009 (3)
C190.053 (4)0.047 (3)0.036 (3)0.006 (3)0.014 (3)0.008 (3)
C200.038 (3)0.039 (3)0.066 (4)0.008 (3)0.008 (3)0.013 (3)
C210.050 (4)0.047 (4)0.053 (4)0.010 (3)0.012 (3)0.002 (3)
C220.039 (4)0.040 (3)0.060 (4)0.006 (3)0.006 (3)0.004 (3)
C230.041 (4)0.067 (4)0.066 (4)0.001 (3)0.012 (3)0.022 (3)
C240.055 (4)0.070 (5)0.086 (5)0.008 (4)0.010 (4)0.034 (4)
C250.034 (4)0.101 (6)0.083 (5)0.000 (4)0.019 (4)0.026 (5)
C260.065 (5)0.082 (5)0.077 (5)0.017 (4)0.012 (4)0.032 (4)
C270.051 (4)0.048 (4)0.044 (4)0.008 (3)0.002 (3)0.005 (3)
C280.030 (3)0.040 (3)0.040 (3)0.003 (3)0.006 (3)0.000 (3)
C290.040 (4)0.047 (4)0.057 (4)0.007 (3)0.009 (3)0.002 (3)
C300.025 (3)0.064 (4)0.075 (5)0.006 (3)0.008 (3)0.006 (4)
C310.069 (5)0.110 (6)0.084 (6)0.004 (5)0.016 (5)0.056 (5)
C320.042 (4)0.085 (5)0.078 (5)0.004 (4)0.007 (4)0.031 (4)
C330.083 (5)0.081 (5)0.075 (5)0.032 (4)0.004 (4)0.029 (4)
Cl10.178 (3)0.1084 (19)0.139 (2)0.0305 (19)0.036 (2)0.0012 (17)
Cl20.0895 (16)0.1205 (19)0.178 (2)0.0245 (14)0.0594 (16)0.0679 (17)
Cl30.1197 (18)0.1078 (16)0.0969 (16)0.0181 (14)0.0459 (14)0.0292 (12)
N10.041 (3)0.034 (2)0.034 (3)0.003 (2)0.012 (2)0.0037 (19)
N20.029 (3)0.039 (3)0.044 (3)0.001 (2)0.013 (2)0.005 (2)
N30.033 (2)0.038 (3)0.032 (3)0.003 (2)0.011 (2)0.0018 (19)
N40.028 (2)0.032 (2)0.040 (3)0.0028 (19)0.003 (2)0.0026 (19)
N50.041 (3)0.044 (3)0.046 (3)0.004 (2)0.011 (2)0.010 (2)
N60.062 (4)0.056 (3)0.090 (5)0.003 (3)0.027 (4)0.017 (3)
N70.030 (2)0.043 (3)0.042 (3)0.003 (2)0.002 (2)0.008 (2)
N80.057 (4)0.079 (4)0.095 (5)0.019 (3)0.005 (4)0.021 (4)
S10.0312 (8)0.0584 (10)0.0680 (11)0.0046 (7)0.0157 (8)0.0022 (8)
S20.0588 (10)0.0434 (9)0.0501 (9)0.0087 (8)0.0122 (8)0.0072 (7)
Geometric parameters (Å, º) top
C1—N51.456 (6)C18—H180.9300
C1—N11.479 (6)C19—N71.449 (6)
C1—H1A0.9700C19—N31.474 (6)
C1—H1B0.9700C19—H19A0.9700
C2—N51.462 (6)C19—H19B0.9700
C2—N21.472 (6)C20—N71.434 (6)
C2—H2A0.9700C20—N41.466 (7)
C2—H2B0.9700C20—H20A0.9700
C3—N11.366 (6)C20—H20B0.9700
C3—N31.368 (6)C21—N51.471 (7)
C3—S21.656 (5)C21—C221.488 (7)
C4—N21.355 (6)C21—H21A0.9700
C4—N41.386 (6)C21—H21B0.9700
C4—S11.657 (5)C22—C261.357 (8)
C5—N21.457 (5)C22—C231.372 (8)
C5—N11.470 (5)C23—C241.356 (8)
C5—C61.527 (7)C23—H230.9300
C5—C121.557 (7)C24—N61.329 (8)
C6—C111.376 (6)C24—H240.9300
C6—C71.385 (6)C25—N61.300 (8)
C7—C81.373 (7)C25—C261.390 (8)
C7—H70.9300C25—H250.9300
C8—C91.370 (7)C26—H260.9300
C8—H80.9300C27—N71.469 (6)
C9—C101.374 (7)C27—C281.481 (7)
C9—H90.9300C27—H27A0.9700
C10—C111.377 (7)C27—H27B0.9700
C10—H100.9300C28—C321.369 (8)
C11—H110.9300C28—C291.386 (7)
C12—N41.448 (6)C29—C301.365 (8)
C12—N31.467 (5)C29—H290.9300
C12—C131.528 (6)C30—N81.316 (8)
C13—C181.350 (7)C30—H300.9300
C13—C141.391 (6)C31—N81.348 (8)
C14—C151.389 (8)C31—C321.368 (9)
C14—H140.9300C31—H310.9300
C15—C161.361 (8)C32—H320.9300
C15—H150.9300C33—Cl21.711 (6)
C16—C171.367 (8)C33—Cl31.724 (7)
C16—H160.9300C33—Cl11.772 (8)
C17—C181.386 (7)C33—H330.9800
C17—H170.9300
N5—C1—N1112.5 (4)N7—C20—H20A108.9
N5—C1—H1A109.1N4—C20—H20A108.9
N1—C1—H1A109.1N7—C20—H20B108.9
N5—C1—H1B109.1N4—C20—H20B108.9
N1—C1—H1B109.1H20A—C20—H20B107.7
H1A—C1—H1B107.8N5—C21—C22112.7 (4)
N5—C2—N2111.2 (4)N5—C21—H21A109.0
N5—C2—H2A109.4C22—C21—H21A109.0
N2—C2—H2A109.4N5—C21—H21B109.0
N5—C2—H2B109.4C22—C21—H21B109.0
N2—C2—H2B109.4H21A—C21—H21B107.8
H2A—C2—H2B108.0C26—C22—C23114.0 (6)
N1—C3—N3108.0 (4)C26—C22—C21122.6 (6)
N1—C3—S2126.4 (4)C23—C22—C21123.4 (6)
N3—C3—S2125.4 (4)C24—C23—C22122.0 (6)
N2—C4—N4108.0 (4)C24—C23—H23119.0
N2—C4—S1126.5 (4)C22—C23—H23119.0
N4—C4—S1125.4 (5)N6—C24—C23123.4 (6)
N2—C5—N1108.9 (4)N6—C24—H24118.3
N2—C5—C6111.8 (3)C23—C24—H24118.3
N1—C5—C6112.8 (4)N6—C25—C26123.5 (7)
N2—C5—C12103.1 (4)N6—C25—H25118.2
N1—C5—C12103.9 (3)C26—C25—H25118.2
C6—C5—C12115.6 (4)C22—C26—C25121.4 (6)
C11—C6—C7118.3 (5)C22—C26—H26119.3
C11—C6—C5120.8 (4)C25—C26—H26119.3
C7—C6—C5120.4 (4)N7—C27—C28111.6 (4)
C8—C7—C6120.9 (5)N7—C27—H27A109.3
C8—C7—H7119.5C28—C27—H27A109.3
C6—C7—H7119.5N7—C27—H27B109.3
C9—C8—C7120.0 (5)C28—C27—H27B109.3
C9—C8—H8120.0H27A—C27—H27B108.0
C7—C8—H8120.0C32—C28—C29115.7 (6)
C8—C9—C10119.9 (6)C32—C28—C27121.4 (5)
C8—C9—H9120.0C29—C28—C27122.8 (5)
C10—C9—H9120.0C30—C29—C28119.3 (6)
C9—C10—C11119.8 (5)C30—C29—H29120.3
C9—C10—H10120.1C28—C29—H29120.3
C11—C10—H10120.1N8—C30—C29126.9 (6)
C6—C11—C10121.0 (5)N8—C30—H30116.5
C6—C11—H11119.5C29—C30—H30116.5
C10—C11—H11119.5N8—C31—C32125.7 (7)
N4—C12—N3109.6 (4)N8—C31—H31117.2
N4—C12—C13112.3 (4)C32—C31—H31117.2
N3—C12—C13112.3 (3)C31—C32—C28120.0 (6)
N4—C12—C5103.0 (3)C31—C32—H32120.0
N3—C12—C5101.7 (4)C28—C32—H32120.0
C13—C12—C5116.9 (4)Cl2—C33—Cl3112.1 (4)
C18—C13—C14119.0 (5)Cl2—C33—Cl1109.7 (4)
C18—C13—C12120.8 (4)Cl3—C33—Cl1108.3 (4)
C14—C13—C12120.2 (4)Cl2—C33—H33108.9
C15—C14—C13119.3 (5)Cl3—C33—H33108.9
C15—C14—H14120.4Cl1—C33—H33108.9
C13—C14—H14120.4C3—N1—C5111.1 (4)
C16—C15—C14120.8 (6)C3—N1—C1123.0 (4)
C16—C15—H15119.6C5—N1—C1114.7 (3)
C14—C15—H15119.6C4—N2—C5112.7 (4)
C15—C16—C17119.8 (6)C4—N2—C2126.8 (4)
C15—C16—H16120.1C5—N2—C2116.3 (4)
C17—C16—H16120.1C3—N3—C12113.4 (4)
C16—C17—C18119.5 (6)C3—N3—C19127.7 (4)
C16—C17—H17120.3C12—N3—C19114.3 (4)
C18—C17—H17120.3C4—N4—C12111.8 (4)
C13—C18—C17121.6 (5)C4—N4—C20124.5 (4)
C13—C18—H18119.2C12—N4—C20113.6 (4)
C17—C18—H18119.2C1—N5—C2110.7 (4)
N7—C19—N3111.8 (4)C1—N5—C21113.8 (4)
N7—C19—H19A109.3C2—N5—C21113.6 (4)
N3—C19—H19A109.3C25—N6—C24115.7 (6)
N7—C19—H19B109.3C20—N7—C19111.5 (4)
N3—C19—H19B109.3C20—N7—C27114.4 (4)
H19A—C19—H19B107.9C19—N7—C27115.4 (4)
N7—C20—N4113.5 (4)C30—N8—C31112.4 (6)
N2—C5—C6—C11162.1 (4)C12—C5—N1—C312.7 (5)
N1—C5—C6—C1138.9 (6)N2—C5—N1—C148.5 (6)
C12—C5—C6—C1180.4 (6)C6—C5—N1—C176.3 (5)
N2—C5—C6—C726.4 (7)C12—C5—N1—C1157.8 (4)
N1—C5—C6—C7149.6 (4)N5—C1—N1—C387.6 (5)
C12—C5—C6—C791.1 (5)N5—C1—N1—C552.9 (6)
C11—C6—C7—C81.8 (8)N4—C4—N2—C58.2 (5)
C5—C6—C7—C8170.0 (5)S1—C4—N2—C5175.2 (3)
C6—C7—C8—C91.8 (9)N4—C4—N2—C2163.9 (4)
C7—C8—C9—C100.8 (10)S1—C4—N2—C219.5 (7)
C8—C9—C10—C110.3 (9)N1—C5—N2—C4108.8 (4)
C7—C6—C11—C100.7 (8)C6—C5—N2—C4125.8 (4)
C5—C6—C11—C10171.0 (5)C12—C5—N2—C41.1 (5)
C9—C10—C11—C60.4 (9)N1—C5—N2—C249.6 (5)
N2—C5—C12—N45.9 (4)C6—C5—N2—C275.7 (5)
N1—C5—C12—N4119.5 (4)C12—C5—N2—C2159.5 (4)
C6—C5—C12—N4116.3 (4)N5—C2—N2—C4101.2 (5)
N2—C5—C12—N3107.6 (4)N5—C2—N2—C553.7 (6)
N1—C5—C12—N36.0 (4)N1—C3—N3—C1210.3 (5)
C6—C5—C12—N3130.1 (4)S2—C3—N3—C12173.6 (3)
N2—C5—C12—C13129.7 (4)N1—C3—N3—C19164.3 (4)
N1—C5—C12—C13116.7 (4)S2—C3—N3—C1919.6 (7)
C6—C5—C12—C137.4 (5)N4—C12—N3—C3106.3 (5)
N4—C12—C13—C1831.2 (7)C13—C12—N3—C3128.0 (4)
N3—C12—C13—C18155.3 (5)C5—C12—N3—C32.2 (5)
C5—C12—C13—C1887.6 (6)N4—C12—N3—C1951.3 (5)
N4—C12—C13—C14150.7 (5)C13—C12—N3—C1974.4 (5)
N3—C12—C13—C1426.6 (7)C5—C12—N3—C19159.8 (4)
C5—C12—C13—C1490.4 (5)N7—C19—N3—C3101.1 (5)
C18—C13—C14—C150.4 (9)N7—C19—N3—C1252.7 (5)
C12—C13—C14—C15178.6 (5)N2—C4—N4—C1212.5 (5)
C13—C14—C15—C160.9 (10)S1—C4—N4—C12170.8 (3)
C14—C15—C16—C171.4 (11)N2—C4—N4—C20155.4 (4)
C15—C16—C17—C181.5 (11)S1—C4—N4—C2027.9 (6)
C14—C13—C18—C170.5 (9)N3—C12—N4—C496.3 (4)
C12—C13—C18—C17178.6 (5)C13—C12—N4—C4138.1 (4)
C16—C17—C18—C131.1 (10)C5—C12—N4—C411.3 (5)
N5—C21—C22—C26139.0 (6)N3—C12—N4—C2050.8 (5)
N5—C21—C22—C2342.0 (7)C13—C12—N4—C2074.8 (5)
C26—C22—C23—C240.0 (9)C5—C12—N4—C20158.5 (4)
C21—C22—C23—C24179.1 (5)N7—C20—N4—C489.0 (5)
C22—C23—C24—N60.5 (10)N7—C20—N4—C1253.3 (5)
C23—C22—C26—C250.7 (9)N1—C1—N5—C253.9 (6)
C21—C22—C26—C25178.4 (5)N1—C1—N5—C2175.5 (6)
N6—C25—C26—C222.0 (11)N2—C2—N5—C153.5 (6)
N7—C27—C28—C3243.3 (7)N2—C2—N5—C2176.0 (5)
N7—C27—C28—C29140.3 (5)C22—C21—N5—C1165.7 (4)
C32—C28—C29—C300.2 (8)C22—C21—N5—C266.4 (6)
C27—C28—C29—C30176.3 (5)C26—C25—N6—C242.3 (10)
C28—C29—C30—N80.1 (9)C23—C24—N6—C251.6 (10)
N8—C31—C32—C280.0 (12)N4—C20—N7—C1952.5 (6)
C29—C28—C32—C310.3 (9)N4—C20—N7—C2780.7 (5)
C27—C28—C32—C31176.3 (6)N3—C19—N7—C2051.7 (5)
N3—C3—N1—C514.4 (5)N3—C19—N7—C2781.0 (5)
S2—C3—N1—C5169.5 (3)C28—C27—N7—C2072.7 (5)
N3—C3—N1—C1156.2 (4)C28—C27—N7—C19155.9 (4)
S2—C3—N1—C127.7 (6)C29—C30—N8—C310.4 (9)
N2—C5—N1—C396.7 (5)C32—C31—N8—C300.3 (11)
C6—C5—N1—C3138.6 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C33—H33···N8i0.982.333.168 (9)142 (8)
Symmetry code: (i) x+2, y+1, z+1.

Experimental details

Crystal data
Chemical formulaC32H30N8S2·CHCl3
Mr710.13
Crystal system, space groupTriclinic, P1
Temperature (K)294
a, b, c (Å)9.5381 (6), 12.1712 (8), 14.8765 (9)
α, β, γ (°)100.978 (1), 91.699 (1), 98.500 (1)
V3)1673.81 (18)
Z2
Radiation typeMo Kα
µ (mm1)0.44
Crystal size (mm)0.20 × 0.10 × 0.10
Data collection
DiffractometerBruker SMART APEX CCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
11061, 5690, 2136
Rint0.109
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.062, 0.210, 0.85
No. of reflections5690
No. of parameters415
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.47, 0.39

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C33—H33···N8i0.9792.3323.168 (9)142 (8)
Symmetry code: (i) x+2, y+1, z+1.
 

Acknowledgements

The authors are grateful to the Central China Normal University for financial support and to Dr Xiang-Gao Meng for the X-ray data collection.

References

First citationBroan, C. J., Butler, A. R., Reed, D. & Sadler, I. H. (1989). J. Chem. Soc. Perkin Trans. 2, pp. 731–740.  CrossRef Google Scholar
First citationBruker (1997). SMART. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationLi, Y. T., Meng, X. G., Cao, L. P., Wang, Y. Z., Yin, G. D., Gao, M., Wen, L. L. & Wu, A. X. (2008). Cryst. Growth Des. 8, 1645–1653.  Web of Science CSD CrossRef Google Scholar
First citationRowan, A. E., Elemans, J. A. A. W. & Nolte, R. J. M. (1999). Acc. Chem. Res. 32, 995–1006.  Web of Science CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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