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

Deng, C.; Shu, W.; Zhang, D.

doi:10.1107/S1600536810020040

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1524

doi:10.1107/S1600536810020040

Open

access

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

Cong Deng,^a ^* Wenming Shu ^a and Dongxue Zhang ^a

^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 ). For the preparation of the title compound, see: Broan et al. (1989 ); Li et al. (2008 ).

Experimental

Crystal data

C₃₂H₃₀N₈S₂·CHCl₃
M_r = 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)
R_int = 0.109

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.210
S = 0.85
5690 reflections
415 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 ); cell refinement: SAINT (Bruker, 1999 ); data reduction: SAINT; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810020040/cv2714sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810020040/cv2714Isup2.hkl

checkCIF report

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.

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

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·CHCl₃	V = 1673.81 (18) Å³
M_r = 710.13	Z = 2
Triclinic, P1	F(000) = 736
Hall symbol: -P 1	D_x = 1.409 Mg m⁻³
a = 9.5381 (6) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.1712 (8) Å	µ = 0.44 mm⁻¹
c = 14.8765 (9) Å	T = 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 tube	R_int = 0.109
Graphite monochromator	θ_max = 25.0°, θ_min = 1.7°
phi and ω scans	h = −11→11
11061 measured reflections	k = −14→13
5690 independent reflections	l = −17→17

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.210	H-atom parameters constrained
S = 0.85	w = 1/[σ²(F_o²) + (0.1041P)²] where P = (F_o² + 2F_c²)/3
5690 reflections	(Δ/σ)_max = 0.001
415 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₃₂H₃₀N₈S₂·CHCl₃	γ = 98.500 (1)°
M_r = 710.13	V = 1673.81 (18) Å³
Triclinic, P1	Z = 2
a = 9.5381 (6) Å	Mo Kα radiation
b = 12.1712 (8) Å	µ = 0.44 mm⁻¹
c = 14.8765 (9) Å	T = 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 reflections	R_int = 0.109
5690 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	0 restraints
wR(F²) = 0.210	H-atom parameters constrained
S = 0.85	Δρ_max = 0.47 e Å⁻³
5690 reflections	Δρ_min = −0.39 e Å⁻³
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

	x	y	z	U_iso*/U_eq
C1	0.4638 (5)	0.4696 (4)	0.1361 (4)	0.0426 (14)
H1A	0.4056	0.4515	0.0790	0.051*
H1B	0.4486	0.5435	0.1685	0.051*
C2	0.6423 (6)	0.3623 (4)	0.0735 (4)	0.0461 (15)
H2A	0.7434	0.3659	0.0658	0.055*
H2B	0.5934	0.3385	0.0133	0.055*
C3	0.4314 (5)	0.4077 (4)	0.2860 (4)	0.0395 (14)
C4	0.6795 (5)	0.2382 (4)	0.1877 (4)	0.0391 (14)
C5	0.4489 (5)	0.2700 (4)	0.1553 (3)	0.0295 (12)
C6	0.3463 (5)	0.2069 (4)	0.0750 (3)	0.0344 (13)
C7	0.3908 (6)	0.1281 (5)	0.0063 (4)	0.0518 (16)
H7	0.4868	0.1222	0.0040	0.062*
C8	0.2952 (6)	0.0585 (5)	−0.0584 (4)	0.0565 (17)
H8	0.3262	0.0045	−0.1031	0.068*
C9	0.1541 (7)	0.0688 (5)	−0.0572 (4)	0.0590 (17)
H9	0.0895	0.0223	−0.1014	0.071*
C10	0.1082 (6)	0.1478 (5)	0.0096 (4)	0.0546 (16)
H10	0.0125	0.1551	0.0104	0.065*
C11	0.2042 (6)	0.2160 (4)	0.0753 (4)	0.0436 (15)
H11	0.1725	0.2690	0.1205	0.052*
C12	0.4498 (5)	0.2132 (4)	0.2406 (3)	0.0322 (13)
C13	0.3367 (5)	0.1100 (4)	0.2397 (3)	0.0351 (13)
C14	0.2062 (6)	0.1236 (5)	0.2759 (4)	0.0567 (17)
H14	0.1877	0.1954	0.3020	0.068*
C15	0.1037 (7)	0.0290 (6)	0.2726 (4)	0.0675 (19)
H15	0.0167	0.0376	0.2975	0.081*
C16	0.1289 (7)	−0.0762 (6)	0.2335 (5)	0.077 (2)
H16	0.0588	−0.1389	0.2304	0.093*
C17	0.2577 (7)	−0.0896 (5)	0.1986 (5)	0.072 (2)
H17	0.2765	−0.1614	0.1730	0.086*
C18	0.3601 (6)	0.0048 (5)	0.2017 (4)	0.0570 (17)
H18	0.4470	−0.0045	0.1770	0.068*
C19	0.4813 (6)	0.2929 (4)	0.4068 (3)	0.0455 (15)
H19A	0.4783	0.3621	0.4511	0.055*
H19B	0.4162	0.2327	0.4245	0.055*
C20	0.6388 (6)	0.1716 (4)	0.3368 (4)	0.0469 (15)
H20A	0.5837	0.1033	0.3497	0.056*
H20B	0.7376	0.1611	0.3364	0.056*
C21	0.7120 (6)	0.5325 (5)	0.1933 (4)	0.0530 (16)
H21A	0.7130	0.4839	0.2379	0.064*
H21B	0.6786	0.6012	0.2227	0.064*
C22	0.8592 (6)	0.5619 (4)	0.1653 (4)	0.0482 (16)
C23	0.8900 (6)	0.6050 (5)	0.0882 (4)	0.0577 (17)
H23	0.8157	0.6157	0.0505	0.069*
C24	1.0254 (7)	0.6325 (5)	0.0652 (5)	0.068 (2)
H24	1.0400	0.6619	0.0124	0.081*
C25	1.1118 (7)	0.5806 (6)	0.1887 (5)	0.073 (2)
H25	1.1882	0.5730	0.2261	0.088*
C26	0.9754 (8)	0.5499 (6)	0.2152 (5)	0.075 (2)
H26	0.9635	0.5204	0.2682	0.090*
C27	0.7389 (6)	0.3621 (5)	0.4180 (4)	0.0481 (15)
H27A	0.7105	0.4275	0.4570	0.058*
H27B	0.7554	0.3804	0.3582	0.058*
C28	0.8721 (5)	0.3375 (4)	0.4579 (4)	0.0384 (14)
C29	1.0046 (6)	0.3720 (4)	0.4278 (4)	0.0505 (16)
H29	1.0126	0.4087	0.3784	0.061*
C30	1.1231 (6)	0.3516 (5)	0.4715 (5)	0.0576 (18)
H30	1.2098	0.3761	0.4491	0.069*
C31	0.9976 (8)	0.2679 (6)	0.5694 (5)	0.084 (2)
H31	0.9927	0.2311	0.6189	0.101*
C32	0.8720 (7)	0.2838 (6)	0.5309 (5)	0.0676 (19)
H32	0.7865	0.2582	0.5542	0.081*
C33	0.6754 (7)	0.8554 (6)	0.3853 (5)	0.076 (2)
H33	0.6949	0.7839	0.4001	0.091*
Cl1	0.7802 (3)	0.9693 (2)	0.4618 (2)	0.1451 (11)
Cl2	0.4992 (2)	0.86364 (19)	0.39764 (19)	0.1222 (10)
Cl3	0.7234 (2)	0.86119 (18)	0.27531 (15)	0.1061 (8)
N1	0.4182 (4)	0.3843 (3)	0.1924 (3)	0.0370 (11)
N2	0.5961 (4)	0.2785 (3)	0.1304 (3)	0.0380 (12)
N3	0.4351 (4)	0.3080 (3)	0.3151 (3)	0.0349 (11)
N4	0.5925 (4)	0.1866 (3)	0.2456 (3)	0.0342 (11)
N5	0.6126 (5)	0.4746 (4)	0.1154 (3)	0.0446 (12)
N6	1.1383 (6)	0.6195 (4)	0.1144 (5)	0.0697 (17)
N7	0.6238 (4)	0.2652 (3)	0.4087 (3)	0.0388 (11)
N8	1.1278 (6)	0.3010 (5)	0.5420 (5)	0.0756 (17)
S1	0.85378 (14)	0.24229 (12)	0.18583 (10)	0.0545 (5)
S2	0.43168 (16)	0.53272 (12)	0.35358 (10)	0.0527 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.042 (3)	0.042 (3)	0.044 (3)	0.002 (3)	0.006 (3)	0.013 (3)
C2	0.042 (3)	0.056 (4)	0.040 (3)	0.002 (3)	0.015 (3)	0.009 (3)
C3	0.026 (3)	0.050 (4)	0.046 (4)	0.009 (3)	0.014 (3)	0.012 (3)
C4	0.038 (3)	0.028 (3)	0.046 (3)	0.004 (3)	0.014 (3)	−0.006 (2)
C5	0.025 (3)	0.032 (3)	0.031 (3)	0.006 (2)	0.004 (2)	0.003 (2)
C6	0.039 (3)	0.032 (3)	0.032 (3)	0.001 (2)	0.010 (3)	0.006 (2)
C7	0.039 (3)	0.055 (4)	0.052 (4)	−0.002 (3)	0.013 (3)	−0.009 (3)
C8	0.047 (4)	0.063 (4)	0.047 (4)	0.000 (3)	0.006 (3)	−0.012 (3)
C9	0.061 (4)	0.058 (4)	0.046 (4)	−0.009 (3)	−0.003 (3)	−0.005 (3)
C10	0.034 (3)	0.055 (4)	0.072 (5)	−0.003 (3)	−0.002 (3)	0.014 (3)
C11	0.042 (3)	0.040 (3)	0.046 (4)	0.002 (3)	0.014 (3)	0.005 (3)
C12	0.026 (3)	0.032 (3)	0.037 (3)	0.001 (2)	0.007 (2)	0.005 (2)
C13	0.035 (3)	0.038 (3)	0.034 (3)	−0.002 (3)	0.000 (3)	0.015 (2)
C14	0.050 (4)	0.060 (4)	0.054 (4)	−0.006 (3)	0.018 (3)	0.007 (3)
C15	0.046 (4)	0.090 (5)	0.058 (4)	−0.019 (4)	0.009 (3)	0.013 (4)
C16	0.066 (5)	0.066 (5)	0.091 (5)	−0.026 (4)	0.008 (4)	0.020 (4)
C17	0.066 (5)	0.038 (4)	0.104 (6)	−0.006 (3)	−0.002 (4)	0.007 (4)
C18	0.044 (4)	0.039 (4)	0.083 (5)	−0.007 (3)	0.009 (3)	0.009 (3)
C19	0.053 (4)	0.047 (3)	0.036 (3)	0.006 (3)	0.014 (3)	0.008 (3)
C20	0.038 (3)	0.039 (3)	0.066 (4)	0.008 (3)	0.008 (3)	0.013 (3)
C21	0.050 (4)	0.047 (4)	0.053 (4)	−0.010 (3)	0.012 (3)	0.002 (3)
C22	0.039 (4)	0.040 (3)	0.060 (4)	−0.006 (3)	0.006 (3)	0.004 (3)
C23	0.041 (4)	0.067 (4)	0.066 (4)	0.001 (3)	0.012 (3)	0.022 (3)
C24	0.055 (4)	0.070 (5)	0.086 (5)	0.008 (4)	0.010 (4)	0.034 (4)
C25	0.034 (4)	0.101 (6)	0.083 (5)	0.000 (4)	−0.019 (4)	0.026 (5)
C26	0.065 (5)	0.082 (5)	0.077 (5)	−0.017 (4)	0.012 (4)	0.032 (4)
C27	0.051 (4)	0.048 (4)	0.044 (4)	0.008 (3)	0.002 (3)	0.005 (3)
C28	0.030 (3)	0.040 (3)	0.040 (3)	0.003 (3)	−0.006 (3)	0.000 (3)
C29	0.040 (4)	0.047 (4)	0.057 (4)	−0.007 (3)	0.009 (3)	0.002 (3)
C30	0.025 (3)	0.064 (4)	0.075 (5)	0.006 (3)	−0.008 (3)	−0.006 (4)
C31	0.069 (5)	0.110 (6)	0.084 (6)	0.004 (5)	−0.016 (5)	0.056 (5)
C32	0.042 (4)	0.085 (5)	0.078 (5)	−0.004 (4)	0.007 (4)	0.031 (4)
C33	0.083 (5)	0.081 (5)	0.075 (5)	0.032 (4)	0.004 (4)	0.029 (4)
Cl1	0.178 (3)	0.1084 (19)	0.139 (2)	0.0305 (19)	−0.036 (2)	0.0012 (17)
Cl2	0.0895 (16)	0.1205 (19)	0.178 (2)	0.0245 (14)	0.0594 (16)	0.0679 (17)
Cl3	0.1197 (18)	0.1078 (16)	0.0969 (16)	0.0181 (14)	0.0459 (14)	0.0292 (12)
N1	0.041 (3)	0.034 (2)	0.034 (3)	0.003 (2)	0.012 (2)	0.0037 (19)
N2	0.029 (3)	0.039 (3)	0.044 (3)	−0.001 (2)	0.013 (2)	0.005 (2)
N3	0.033 (2)	0.038 (3)	0.032 (3)	0.003 (2)	0.011 (2)	0.0018 (19)
N4	0.028 (2)	0.032 (2)	0.040 (3)	0.0028 (19)	0.003 (2)	0.0026 (19)
N5	0.041 (3)	0.044 (3)	0.046 (3)	−0.004 (2)	0.011 (2)	0.010 (2)
N6	0.062 (4)	0.056 (3)	0.090 (5)	−0.003 (3)	0.027 (4)	0.017 (3)
N7	0.030 (2)	0.043 (3)	0.042 (3)	0.003 (2)	0.002 (2)	0.008 (2)
N8	0.057 (4)	0.079 (4)	0.095 (5)	0.019 (3)	−0.005 (4)	0.021 (4)
S1	0.0312 (8)	0.0584 (10)	0.0680 (11)	0.0046 (7)	0.0157 (8)	−0.0022 (8)
S2	0.0588 (10)	0.0434 (9)	0.0501 (9)	0.0087 (8)	0.0122 (8)	−0.0072 (7)

Geometric parameters (Å, º) top

C1—N5	1.456 (6)	C18—H18	0.9300
C1—N1	1.479 (6)	C19—N7	1.449 (6)
C1—H1A	0.9700	C19—N3	1.474 (6)
C1—H1B	0.9700	C19—H19A	0.9700
C2—N5	1.462 (6)	C19—H19B	0.9700
C2—N2	1.472 (6)	C20—N7	1.434 (6)
C2—H2A	0.9700	C20—N4	1.466 (7)
C2—H2B	0.9700	C20—H20A	0.9700
C3—N1	1.366 (6)	C20—H20B	0.9700
C3—N3	1.368 (6)	C21—N5	1.471 (7)
C3—S2	1.656 (5)	C21—C22	1.488 (7)
C4—N2	1.355 (6)	C21—H21A	0.9700
C4—N4	1.386 (6)	C21—H21B	0.9700
C4—S1	1.657 (5)	C22—C26	1.357 (8)
C5—N2	1.457 (5)	C22—C23	1.372 (8)
C5—N1	1.470 (5)	C23—C24	1.356 (8)
C5—C6	1.527 (7)	C23—H23	0.9300
C5—C12	1.557 (7)	C24—N6	1.329 (8)
C6—C11	1.376 (6)	C24—H24	0.9300
C6—C7	1.385 (6)	C25—N6	1.300 (8)
C7—C8	1.373 (7)	C25—C26	1.390 (8)
C7—H7	0.9300	C25—H25	0.9300
C8—C9	1.370 (7)	C26—H26	0.9300
C8—H8	0.9300	C27—N7	1.469 (6)
C9—C10	1.374 (7)	C27—C28	1.481 (7)
C9—H9	0.9300	C27—H27A	0.9700
C10—C11	1.377 (7)	C27—H27B	0.9700
C10—H10	0.9300	C28—C32	1.369 (8)
C11—H11	0.9300	C28—C29	1.386 (7)
C12—N4	1.448 (6)	C29—C30	1.365 (8)
C12—N3	1.467 (5)	C29—H29	0.9300
C12—C13	1.528 (6)	C30—N8	1.316 (8)
C13—C18	1.350 (7)	C30—H30	0.9300
C13—C14	1.391 (6)	C31—N8	1.348 (8)
C14—C15	1.389 (8)	C31—C32	1.368 (9)
C14—H14	0.9300	C31—H31	0.9300
C15—C16	1.361 (8)	C32—H32	0.9300
C15—H15	0.9300	C33—Cl2	1.711 (6)
C16—C17	1.367 (8)	C33—Cl3	1.724 (7)
C16—H16	0.9300	C33—Cl1	1.772 (8)
C17—C18	1.386 (7)	C33—H33	0.9800
C17—H17	0.9300

N5—C1—N1	112.5 (4)	N7—C20—H20A	108.9
N5—C1—H1A	109.1	N4—C20—H20A	108.9
N1—C1—H1A	109.1	N7—C20—H20B	108.9
N5—C1—H1B	109.1	N4—C20—H20B	108.9
N1—C1—H1B	109.1	H20A—C20—H20B	107.7
H1A—C1—H1B	107.8	N5—C21—C22	112.7 (4)
N5—C2—N2	111.2 (4)	N5—C21—H21A	109.0
N5—C2—H2A	109.4	C22—C21—H21A	109.0
N2—C2—H2A	109.4	N5—C21—H21B	109.0
N5—C2—H2B	109.4	C22—C21—H21B	109.0
N2—C2—H2B	109.4	H21A—C21—H21B	107.8
H2A—C2—H2B	108.0	C26—C22—C23	114.0 (6)
N1—C3—N3	108.0 (4)	C26—C22—C21	122.6 (6)
N1—C3—S2	126.4 (4)	C23—C22—C21	123.4 (6)
N3—C3—S2	125.4 (4)	C24—C23—C22	122.0 (6)
N2—C4—N4	108.0 (4)	C24—C23—H23	119.0
N2—C4—S1	126.5 (4)	C22—C23—H23	119.0
N4—C4—S1	125.4 (5)	N6—C24—C23	123.4 (6)
N2—C5—N1	108.9 (4)	N6—C24—H24	118.3
N2—C5—C6	111.8 (3)	C23—C24—H24	118.3
N1—C5—C6	112.8 (4)	N6—C25—C26	123.5 (7)
N2—C5—C12	103.1 (4)	N6—C25—H25	118.2
N1—C5—C12	103.9 (3)	C26—C25—H25	118.2
C6—C5—C12	115.6 (4)	C22—C26—C25	121.4 (6)
C11—C6—C7	118.3 (5)	C22—C26—H26	119.3
C11—C6—C5	120.8 (4)	C25—C26—H26	119.3
C7—C6—C5	120.4 (4)	N7—C27—C28	111.6 (4)
C8—C7—C6	120.9 (5)	N7—C27—H27A	109.3
C8—C7—H7	119.5	C28—C27—H27A	109.3
C6—C7—H7	119.5	N7—C27—H27B	109.3
C9—C8—C7	120.0 (5)	C28—C27—H27B	109.3
C9—C8—H8	120.0	H27A—C27—H27B	108.0
C7—C8—H8	120.0	C32—C28—C29	115.7 (6)
C8—C9—C10	119.9 (6)	C32—C28—C27	121.4 (5)
C8—C9—H9	120.0	C29—C28—C27	122.8 (5)
C10—C9—H9	120.0	C30—C29—C28	119.3 (6)
C9—C10—C11	119.8 (5)	C30—C29—H29	120.3
C9—C10—H10	120.1	C28—C29—H29	120.3
C11—C10—H10	120.1	N8—C30—C29	126.9 (6)
C6—C11—C10	121.0 (5)	N8—C30—H30	116.5
C6—C11—H11	119.5	C29—C30—H30	116.5
C10—C11—H11	119.5	N8—C31—C32	125.7 (7)
N4—C12—N3	109.6 (4)	N8—C31—H31	117.2
N4—C12—C13	112.3 (4)	C32—C31—H31	117.2
N3—C12—C13	112.3 (3)	C31—C32—C28	120.0 (6)
N4—C12—C5	103.0 (3)	C31—C32—H32	120.0
N3—C12—C5	101.7 (4)	C28—C32—H32	120.0
C13—C12—C5	116.9 (4)	Cl2—C33—Cl3	112.1 (4)
C18—C13—C14	119.0 (5)	Cl2—C33—Cl1	109.7 (4)
C18—C13—C12	120.8 (4)	Cl3—C33—Cl1	108.3 (4)
C14—C13—C12	120.2 (4)	Cl2—C33—H33	108.9
C15—C14—C13	119.3 (5)	Cl3—C33—H33	108.9
C15—C14—H14	120.4	Cl1—C33—H33	108.9
C13—C14—H14	120.4	C3—N1—C5	111.1 (4)
C16—C15—C14	120.8 (6)	C3—N1—C1	123.0 (4)
C16—C15—H15	119.6	C5—N1—C1	114.7 (3)
C14—C15—H15	119.6	C4—N2—C5	112.7 (4)
C15—C16—C17	119.8 (6)	C4—N2—C2	126.8 (4)
C15—C16—H16	120.1	C5—N2—C2	116.3 (4)
C17—C16—H16	120.1	C3—N3—C12	113.4 (4)
C16—C17—C18	119.5 (6)	C3—N3—C19	127.7 (4)
C16—C17—H17	120.3	C12—N3—C19	114.3 (4)
C18—C17—H17	120.3	C4—N4—C12	111.8 (4)
C13—C18—C17	121.6 (5)	C4—N4—C20	124.5 (4)
C13—C18—H18	119.2	C12—N4—C20	113.6 (4)
C17—C18—H18	119.2	C1—N5—C2	110.7 (4)
N7—C19—N3	111.8 (4)	C1—N5—C21	113.8 (4)
N7—C19—H19A	109.3	C2—N5—C21	113.6 (4)
N3—C19—H19A	109.3	C25—N6—C24	115.7 (6)
N7—C19—H19B	109.3	C20—N7—C19	111.5 (4)
N3—C19—H19B	109.3	C20—N7—C27	114.4 (4)
H19A—C19—H19B	107.9	C19—N7—C27	115.4 (4)
N7—C20—N4	113.5 (4)	C30—N8—C31	112.4 (6)

N2—C5—C6—C11	−162.1 (4)	C12—C5—N1—C3	12.7 (5)
N1—C5—C6—C11	−38.9 (6)	N2—C5—N1—C1	48.5 (6)
C12—C5—C6—C11	80.4 (6)	C6—C5—N1—C1	−76.3 (5)
N2—C5—C6—C7	26.4 (7)	C12—C5—N1—C1	157.8 (4)
N1—C5—C6—C7	149.6 (4)	N5—C1—N1—C3	87.6 (5)
C12—C5—C6—C7	−91.1 (5)	N5—C1—N1—C5	−52.9 (6)
C11—C6—C7—C8	−1.8 (8)	N4—C4—N2—C5	8.2 (5)
C5—C6—C7—C8	170.0 (5)	S1—C4—N2—C5	−175.2 (3)
C6—C7—C8—C9	1.8 (9)	N4—C4—N2—C2	163.9 (4)
C7—C8—C9—C10	−0.8 (10)	S1—C4—N2—C2	−19.5 (7)
C8—C9—C10—C11	−0.3 (9)	N1—C5—N2—C4	108.8 (4)
C7—C6—C11—C10	0.7 (8)	C6—C5—N2—C4	−125.8 (4)
C5—C6—C11—C10	−171.0 (5)	C12—C5—N2—C4	−1.1 (5)
C9—C10—C11—C6	0.4 (9)	N1—C5—N2—C2	−49.6 (5)
N2—C5—C12—N4	−5.9 (4)	C6—C5—N2—C2	75.7 (5)
N1—C5—C12—N4	−119.5 (4)	C12—C5—N2—C2	−159.5 (4)
C6—C5—C12—N4	116.3 (4)	N5—C2—N2—C4	−101.2 (5)
N2—C5—C12—N3	107.6 (4)	N5—C2—N2—C5	53.7 (6)
N1—C5—C12—N3	−6.0 (4)	N1—C3—N3—C12	10.3 (5)
C6—C5—C12—N3	−130.1 (4)	S2—C3—N3—C12	−173.6 (3)
N2—C5—C12—C13	−129.7 (4)	N1—C3—N3—C19	164.3 (4)
N1—C5—C12—C13	116.7 (4)	S2—C3—N3—C19	−19.6 (7)
C6—C5—C12—C13	−7.4 (5)	N4—C12—N3—C3	106.3 (5)
N4—C12—C13—C18	−31.2 (7)	C13—C12—N3—C3	−128.0 (4)
N3—C12—C13—C18	−155.3 (5)	C5—C12—N3—C3	−2.2 (5)
C5—C12—C13—C18	87.6 (6)	N4—C12—N3—C19	−51.3 (5)
N4—C12—C13—C14	150.7 (5)	C13—C12—N3—C19	74.4 (5)
N3—C12—C13—C14	26.6 (7)	C5—C12—N3—C19	−159.8 (4)
C5—C12—C13—C14	−90.4 (5)	N7—C19—N3—C3	−101.1 (5)
C18—C13—C14—C15	0.4 (9)	N7—C19—N3—C12	52.7 (5)
C12—C13—C14—C15	178.6 (5)	N2—C4—N4—C12	−12.5 (5)
C13—C14—C15—C16	−0.9 (10)	S1—C4—N4—C12	170.8 (3)
C14—C15—C16—C17	1.4 (11)	N2—C4—N4—C20	−155.4 (4)
C15—C16—C17—C18	−1.5 (11)	S1—C4—N4—C20	27.9 (6)
C14—C13—C18—C17	−0.5 (9)	N3—C12—N4—C4	−96.3 (4)
C12—C13—C18—C17	−178.6 (5)	C13—C12—N4—C4	138.1 (4)
C16—C17—C18—C13	1.1 (10)	C5—C12—N4—C4	11.3 (5)
N5—C21—C22—C26	−139.0 (6)	N3—C12—N4—C20	50.8 (5)
N5—C21—C22—C23	42.0 (7)	C13—C12—N4—C20	−74.8 (5)
C26—C22—C23—C24	0.0 (9)	C5—C12—N4—C20	158.5 (4)
C21—C22—C23—C24	179.1 (5)	N7—C20—N4—C4	89.0 (5)
C22—C23—C24—N6	0.5 (10)	N7—C20—N4—C12	−53.3 (5)
C23—C22—C26—C25	0.7 (9)	N1—C1—N5—C2	53.9 (6)
C21—C22—C26—C25	−178.4 (5)	N1—C1—N5—C21	−75.5 (6)
N6—C25—C26—C22	−2.0 (11)	N2—C2—N5—C1	−53.5 (6)
N7—C27—C28—C32	−43.3 (7)	N2—C2—N5—C21	76.0 (5)
N7—C27—C28—C29	140.3 (5)	C22—C21—N5—C1	−165.7 (4)
C32—C28—C29—C30	−0.2 (8)	C22—C21—N5—C2	66.4 (6)
C27—C28—C29—C30	176.3 (5)	C26—C25—N6—C24	2.3 (10)
C28—C29—C30—N8	−0.1 (9)	C23—C24—N6—C25	−1.6 (10)
N8—C31—C32—C28	0.0 (12)	N4—C20—N7—C19	52.5 (6)
C29—C28—C32—C31	0.3 (9)	N4—C20—N7—C27	−80.7 (5)
C27—C28—C32—C31	−176.3 (6)	N3—C19—N7—C20	−51.7 (5)
N3—C3—N1—C5	−14.4 (5)	N3—C19—N7—C27	81.0 (5)
S2—C3—N1—C5	169.5 (3)	C28—C27—N7—C20	−72.7 (5)
N3—C3—N1—C1	−156.2 (4)	C28—C27—N7—C19	155.9 (4)
S2—C3—N1—C1	27.7 (6)	C29—C30—N8—C31	0.4 (9)
N2—C5—N1—C3	−96.7 (5)	C32—C31—N8—C30	−0.3 (11)
C6—C5—N1—C3	138.6 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C33—H33···N8ⁱ	0.98	2.33	3.168 (9)	142 (8)

Symmetry code: (i) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₃₂H₃₀N₈S₂·CHCl₃
M_r	710.13
Crystal system, space group	Triclinic, 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)
V (Å³)	1673.81 (18)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.44
Crystal size (mm)	0.20 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	11061, 5690, 2136
R_int	0.109
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.210, 0.85
No. of reflections	5690
No. of parameters	415
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	D—H···A
C33—H33···N8ⁱ	0.979	2.332	3.168 (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

Broan, C. J., Butler, A. R., Reed, D. & Sadler, I. H. (1989). J. Chem. Soc. Perkin Trans. 2, pp. 731–740. CrossRef Google Scholar
Bruker (1997). SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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. Web of Science CSD CrossRef Google Scholar
Rowan, 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
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1524

doi:10.1107/S1600536810020040

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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