2,6-Bis(2-chloro­ethyl)-8b,8c-diphenyl­perhydro-2,3a,4a,6,7a,8a-hexa­azacyclo­penta­[def]fluorene-4,8-dithione

Wu, Y.; Sun, Y.

doi:10.1107/S1600536809024118

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page o1715

doi:10.1107/S1600536809024118

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2,6-Bis(2-chloroethyl)-8b,8c-diphenylperhydro-2,3a,4a,6,7a,8a-hexaazacyclopenta[def]fluorene-4,8-dithione

Yandong Wu ^a ^* and Yichong Sun ^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: wyd851201@126.com

(Received 16 June 2009; accepted 23 June 2009; online 27 June 2009)

In the title molecule, C₂₄H₂₆Cl₂N₆S₂, the two phenyl rings form a dihedral angle of 51.95 (7)° and the distance between their centroids is 4.156 (8) Å. The crystal packing exhibits weak intermolecular C—H⋯S and C—H⋯N hydrogen bonds.

Related literature

For applications of glycoluril derivatives, see: Wu et al. (2002 ). For a related structure, see: Wang & Xi (2009 ). For details of the synthesis, see: Ramos & Rosen (1981 ).

Experimental

Crystal data

C₂₄H₂₆Cl₂N₆S₂
M_r = 533.53
Monoclinic, P 2₁ /c
a = 8.7566 (2) Å
b = 14.0877 (3) Å
c = 20.8575 (5) Å
β = 99.525 (1)°
V = 2537.52 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.45 mm⁻¹
T = 298 K
0.23 × 0.20 × 0.10 mm

Data collection

Bruker SMART 4K CCD area-detector diffractometer
Absorption correction: none
16129 measured reflections
4979 independent reflections
3375 reflections with I > 2σ(I)
R_int = 0.078

Refinement

R[F² > 2σ(F²)] = 0.064
wR(F²) = 0.164
S = 1.02
4979 reflections
307 parameters
H-atom parameters constrained
Δρ_max = 0.63 e Å⁻³
Δρ_min = −0.51 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C24—H24B⋯N1ⁱ	0.97	2.55	3.485 (4)	162
C22—H22B⋯S1ⁱⁱ	0.97	2.80	3.607 (3)	141
Symmetry codes: (i) x-1, y, z; (ii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809024118/cv2576sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809024118/cv2576Isup2.hkl

checkCIF report

Comment top

Glycoluril derivatives have many areas of applications, such as explosives, slow-release fertilizers, cross-linkers, stabilizers of organic compounds against photodegradation, and as reagents in combinatorial chemistry (Wu et al., 2002). Also, The rigid concave shape of glycoluril makes it a versatile building block to construct various supramolecular objects (Wang & Xi, 2009). We report here the structure of the title thioglycoluril derivative (Fig. 1), which is a potential receptor in supramolecular chemistry.

In the title compound all bond lengths and angles are normal and comparable with those observed in the related structure (Wang & Xi, 2009). The crystal packing is stabilized by intermolecular C–H···S and C—H···N hydrogen bonds (Table 1).

Related literature top

For applications of glycoluril derivatives, see: Wu et al. (2002). For a related structure, see: Wang & Xi (2009). For details of the synthesis, see: Ramos & Rosen (1981).

Experimental top

The title compound was synthesized according to the procedure reported by Ramos & Rosen (1981). Crystals appropriate for X-ray data collection were obtained by slow evaporation of the dichloromethane solution at 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: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. View of (I) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented by spheres of arbitrary radius.

2,6-Bis(2-chloroethyl)-8b,8c-diphenylperhydro-2,3a,4a,6,7a,8a- hexaazacyclopenta[def]fluorene-4,8-dithione top

Crystal data top

C₂₄H₂₆Cl₂N₆S₂	F(000) = 1112
M_r = 533.53	D_x = 1.397 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2851 reflections
a = 8.7566 (2) Å	θ = 2.5–21.7°
b = 14.0877 (3) Å	µ = 0.45 mm⁻¹
c = 20.8575 (5) Å	T = 298 K
β = 99.525 (1)°	Block, colourless
V = 2537.52 (10) Å³	0.23 × 0.20 × 0.10 mm
Z = 4

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	3375 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.078
Graphite monochromator	θ_max = 26.0°, θ_min = 1.8°
ϕ and ω scans	h = −10→10
16129 measured reflections	k = −17→17
4979 independent reflections	l = −18→25

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)] = 0.064	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.164	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0798P)²] where P = (F_o² + 2F_c²)/3
4979 reflections	(Δ/σ)_max < 0.001
307 parameters	Δρ_max = 0.63 e Å⁻³
0 restraints	Δρ_min = −0.51 e Å⁻³

Crystal data top

C₂₄H₂₆Cl₂N₆S₂	V = 2537.52 (10) Å³
M_r = 533.53	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.7566 (2) Å	µ = 0.45 mm⁻¹
b = 14.0877 (3) Å	T = 298 K
c = 20.8575 (5) Å	0.23 × 0.20 × 0.10 mm
β = 99.525 (1)°

Data collection top

Bruker SMART 4K CCD area-detector diffractometer	3375 reflections with I > 2σ(I)
16129 measured reflections	R_int = 0.078
4979 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.064	0 restraints
wR(F²) = 0.164	H-atom parameters constrained
S = 1.02	Δρ_max = 0.63 e Å⁻³
4979 reflections	Δρ_min = −0.51 e Å⁻³
307 parameters

Special details top

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.

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) top

	x	y	z	U_iso*/U_eq
C1	0.5265 (5)	0.0996 (4)	0.4154 (2)	0.0757 (13)
H1A	0.4497	0.0898	0.4434	0.091*
H1B	0.5458	0.1673	0.4136	0.091*
C2	0.4639 (4)	0.0657 (3)	0.34973 (18)	0.0501 (9)
H2A	0.4466	−0.0022	0.3516	0.060*
H2B	0.3642	0.0956	0.3356	0.060*
C3	0.5429 (3)	0.0178 (2)	0.24750 (17)	0.0394 (8)
H3A	0.5366	−0.0461	0.2641	0.047*
H3B	0.6324	0.0210	0.2257	0.047*
C4	0.5586 (4)	0.1811 (2)	0.27789 (16)	0.0393 (8)
H4A	0.6483	0.1925	0.2572	0.047*
H4B	0.5643	0.2242	0.3145	0.047*
C5	0.2613 (3)	−0.0038 (2)	0.19965 (15)	0.0319 (7)
C6	0.2848 (3)	0.2397 (2)	0.24636 (15)	0.0314 (7)
C7	0.3878 (3)	0.13561 (19)	0.17632 (14)	0.0281 (7)
C8	0.4933 (3)	0.1550 (2)	0.12701 (15)	0.0342 (7)
C9	0.5363 (4)	0.0818 (3)	0.08934 (17)	0.0493 (9)
H9	0.5021	0.0203	0.0947	0.059*
C10	0.6305 (5)	0.1006 (4)	0.0436 (2)	0.0679 (13)
H10	0.6592	0.0516	0.0182	0.081*
C11	0.6819 (5)	0.1918 (4)	0.0354 (2)	0.0725 (14)
H11	0.7445	0.2041	0.0044	0.087*
C12	0.6409 (4)	0.2640 (3)	0.0727 (2)	0.0670 (12)
H12	0.6763	0.3253	0.0676	0.080*
C13	0.5465 (4)	0.2455 (3)	0.11833 (18)	0.0494 (9)
H13	0.5184	0.2949	0.1436	0.059*
C14	0.2095 (3)	0.14683 (19)	0.15257 (14)	0.0278 (7)
C15	0.1585 (3)	0.1754 (2)	0.08262 (15)	0.0336 (7)
C16	0.1323 (4)	0.1075 (3)	0.03430 (17)	0.0496 (9)
H16	0.1440	0.0436	0.0450	0.060*
C17	0.0888 (5)	0.1341 (3)	−0.02984 (19)	0.0687 (12)
H17	0.0719	0.0879	−0.0621	0.082*
C18	0.0703 (5)	0.2282 (4)	−0.0463 (2)	0.0752 (14)
H18	0.0392	0.2458	−0.0894	0.090*
C19	0.0978 (5)	0.2958 (3)	0.0012 (2)	0.0714 (13)
H19	0.0870	0.3597	−0.0098	0.086*
C20	0.1416 (4)	0.2694 (3)	0.06534 (18)	0.0522 (10)
H20	0.1599	0.3159	0.0973	0.063*
C21	−0.0141 (3)	0.0516 (2)	0.17475 (16)	0.0345 (7)
H21A	−0.0784	0.0657	0.1334	0.041*
H21B	−0.0404	−0.0117	0.1876	0.041*
C22	0.0005 (3)	0.2145 (2)	0.20563 (17)	0.0384 (8)
H22A	−0.0628	0.2341	0.1652	0.046*
H22B	−0.0163	0.2593	0.2391	0.046*
C23	0.0225 (4)	0.0944 (2)	0.28981 (15)	0.0383 (8)
H23A	0.0157	0.1485	0.3180	0.046*
H23B	0.1313	0.0806	0.2906	0.046*
C24	−0.0531 (4)	0.0101 (2)	0.31604 (17)	0.0429 (8)
H24A	−0.0589	−0.0425	0.2857	0.052*
H24B	−0.1573	0.0262	0.3223	0.052*
Cl1	0.69817 (17)	0.04249 (16)	0.44949 (7)	0.1337 (8)
Cl2	0.06244 (11)	−0.02216 (7)	0.39222 (5)	0.0585 (3)
N1	0.5631 (3)	0.08436 (18)	0.30145 (13)	0.0382 (7)
N2	0.4172 (3)	0.20160 (16)	0.23108 (12)	0.0304 (6)
N3	0.4014 (3)	0.03855 (16)	0.20014 (13)	0.0301 (6)
N4	0.1644 (3)	0.21709 (16)	0.19809 (12)	0.0303 (6)
N5	0.1496 (3)	0.05305 (16)	0.16642 (12)	0.0289 (6)
N6	−0.0485 (3)	0.11945 (18)	0.22321 (13)	0.0356 (6)
S1	0.23332 (10)	−0.10921 (6)	0.23090 (5)	0.0516 (3)
S2	0.27222 (11)	0.30702 (6)	0.31074 (4)	0.0461 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.065 (3)	0.104 (4)	0.059 (3)	0.015 (3)	0.015 (2)	0.001 (3)
C2	0.041 (2)	0.064 (2)	0.045 (2)	−0.0041 (17)	0.0059 (17)	0.0122 (19)
C3	0.0314 (17)	0.0371 (18)	0.049 (2)	0.0063 (14)	0.0052 (16)	0.0086 (16)
C4	0.0339 (18)	0.0444 (19)	0.040 (2)	−0.0068 (14)	0.0066 (15)	−0.0017 (16)
C5	0.0287 (16)	0.0280 (16)	0.040 (2)	0.0012 (12)	0.0087 (14)	−0.0048 (14)
C6	0.0374 (17)	0.0230 (15)	0.0350 (19)	0.0003 (12)	0.0097 (15)	0.0045 (13)
C7	0.0300 (16)	0.0241 (15)	0.0307 (17)	0.0008 (12)	0.0068 (13)	−0.0010 (13)
C8	0.0279 (16)	0.0418 (19)	0.0333 (18)	−0.0004 (13)	0.0061 (14)	0.0005 (15)
C9	0.042 (2)	0.061 (2)	0.047 (2)	0.0026 (17)	0.0154 (18)	−0.0076 (19)
C10	0.050 (2)	0.112 (4)	0.046 (3)	0.015 (2)	0.023 (2)	−0.014 (2)
C11	0.047 (2)	0.124 (4)	0.051 (3)	−0.011 (3)	0.021 (2)	0.016 (3)
C12	0.057 (3)	0.088 (3)	0.058 (3)	−0.022 (2)	0.015 (2)	0.019 (3)
C13	0.057 (2)	0.051 (2)	0.043 (2)	−0.0113 (17)	0.0161 (18)	0.0069 (17)
C14	0.0305 (16)	0.0233 (15)	0.0313 (17)	0.0030 (12)	0.0105 (13)	−0.0017 (13)
C15	0.0329 (17)	0.0358 (17)	0.0340 (19)	0.0058 (13)	0.0113 (14)	−0.0005 (14)
C16	0.070 (3)	0.044 (2)	0.036 (2)	0.0072 (18)	0.0130 (19)	−0.0031 (17)
C17	0.102 (4)	0.073 (3)	0.031 (2)	0.007 (3)	0.011 (2)	−0.009 (2)
C18	0.093 (4)	0.102 (4)	0.032 (2)	0.020 (3)	0.016 (2)	0.022 (3)
C19	0.103 (4)	0.063 (3)	0.051 (3)	0.023 (2)	0.019 (3)	0.024 (2)
C20	0.073 (3)	0.042 (2)	0.043 (2)	0.0065 (18)	0.012 (2)	0.0064 (18)
C21	0.0276 (16)	0.0409 (18)	0.0349 (19)	−0.0010 (13)	0.0048 (14)	0.0002 (15)
C22	0.0340 (17)	0.0412 (19)	0.041 (2)	0.0118 (14)	0.0105 (15)	−0.0007 (16)
C23	0.0374 (18)	0.0450 (19)	0.034 (2)	−0.0018 (15)	0.0086 (15)	−0.0027 (15)
C24	0.0354 (18)	0.053 (2)	0.041 (2)	−0.0052 (15)	0.0065 (16)	0.0053 (17)
Cl1	0.0874 (10)	0.253 (2)	0.0537 (8)	0.0758 (12)	−0.0083 (7)	0.0002 (10)
Cl2	0.0556 (6)	0.0663 (6)	0.0516 (6)	−0.0015 (5)	0.0029 (5)	0.0170 (5)
N1	0.0297 (14)	0.0429 (16)	0.0413 (17)	0.0002 (12)	0.0033 (12)	0.0062 (13)
N2	0.0316 (14)	0.0296 (13)	0.0307 (15)	−0.0033 (11)	0.0076 (11)	−0.0015 (11)
N3	0.0241 (13)	0.0236 (13)	0.0426 (16)	0.0012 (10)	0.0058 (11)	0.0019 (11)
N4	0.0342 (14)	0.0255 (13)	0.0319 (15)	0.0052 (10)	0.0077 (12)	−0.0022 (11)
N5	0.0270 (13)	0.0264 (13)	0.0340 (15)	−0.0008 (10)	0.0074 (11)	0.0005 (11)
N6	0.0320 (14)	0.0409 (16)	0.0356 (16)	0.0058 (11)	0.0105 (12)	0.0000 (12)
S1	0.0454 (5)	0.0260 (5)	0.0856 (8)	−0.0009 (4)	0.0169 (5)	0.0123 (5)
S2	0.0600 (6)	0.0389 (5)	0.0420 (6)	−0.0011 (4)	0.0163 (5)	−0.0135 (4)

Geometric parameters (Å, º) top

C1—C2	1.469 (6)	C12—C13	1.384 (5)
C1—Cl1	1.749 (4)	C12—H12	0.9300
C1—H1A	0.9700	C13—H13	0.9300
C1—H1B	0.9700	C14—N5	1.468 (3)
C2—N1	1.459 (4)	C14—N4	1.470 (3)
C2—H2A	0.9700	C14—C15	1.508 (4)
C2—H2B	0.9700	C15—C20	1.374 (4)
C3—N1	1.453 (4)	C15—C16	1.381 (4)
C3—N3	1.480 (4)	C16—C17	1.381 (5)
C3—H3A	0.9700	C16—H16	0.9300
C3—H3B	0.9700	C17—C18	1.372 (6)
C4—N1	1.447 (4)	C17—H17	0.9300
C4—N2	1.473 (4)	C18—C19	1.366 (6)
C4—H4A	0.9700	C18—H18	0.9300
C4—H4B	0.9700	C19—C20	1.381 (5)
C5—N5	1.362 (4)	C19—H19	0.9300
C5—N3	1.363 (4)	C20—H20	0.9300
C5—S1	1.656 (3)	C21—N6	1.458 (4)
C6—N2	1.362 (4)	C21—N5	1.472 (4)
C6—N4	1.369 (4)	C21—H21A	0.9700
C6—S2	1.662 (3)	C21—H21B	0.9700
C7—N3	1.453 (3)	C22—N4	1.470 (4)
C7—N2	1.462 (4)	C22—N6	1.471 (4)
C7—C8	1.517 (4)	C22—H22A	0.9700
C7—C14	1.565 (4)	C22—H22B	0.9700
C8—C13	1.379 (4)	C23—N6	1.468 (4)
C8—C9	1.385 (4)	C23—C24	1.506 (4)
C9—C10	1.386 (5)	C23—H23A	0.9700
C9—H9	0.9300	C23—H23B	0.9700
C10—C11	1.381 (6)	C24—Cl2	1.795 (3)
C10—H10	0.9300	C24—H24A	0.9700
C11—C12	1.364 (6)	C24—H24B	0.9700
C11—H11	0.9300

C2—C1—Cl1	113.1 (3)	C20—C15—C16	118.6 (3)
C2—C1—H1A	109.0	C20—C15—C14	120.8 (3)
Cl1—C1—H1A	109.0	C16—C15—C14	120.5 (3)
C2—C1—H1B	109.0	C17—C16—C15	120.4 (3)
Cl1—C1—H1B	109.0	C17—C16—H16	119.8
H1A—C1—H1B	107.8	C15—C16—H16	119.8
N1—C2—C1	114.3 (3)	C18—C17—C16	120.4 (4)
N1—C2—H2A	108.7	C18—C17—H17	119.8
C1—C2—H2A	108.7	C16—C17—H17	119.8
N1—C2—H2B	108.7	C19—C18—C17	119.6 (4)
C1—C2—H2B	108.7	C19—C18—H18	120.2
H2A—C2—H2B	107.6	C17—C18—H18	120.2
N1—C3—N3	111.8 (2)	C18—C19—C20	120.1 (4)
N1—C3—H3A	109.3	C18—C19—H19	120.0
N3—C3—H3A	109.3	C20—C19—H19	120.0
N1—C3—H3B	109.3	C15—C20—C19	121.0 (4)
N3—C3—H3B	109.3	C15—C20—H20	119.5
H3A—C3—H3B	107.9	C19—C20—H20	119.5
N1—C4—N2	112.5 (2)	N6—C21—N5	112.9 (2)
N1—C4—H4A	109.1	N6—C21—H21A	109.0
N2—C4—H4A	109.1	N5—C21—H21A	109.0
N1—C4—H4B	109.1	N6—C21—H21B	109.0
N2—C4—H4B	109.1	N5—C21—H21B	109.0
H4A—C4—H4B	107.8	H21A—C21—H21B	107.8
N5—C5—N3	108.4 (2)	N4—C22—N6	112.3 (2)
N5—C5—S1	126.0 (2)	N4—C22—H22A	109.1
N3—C5—S1	125.5 (2)	N6—C22—H22A	109.1
N2—C6—N4	108.5 (3)	N4—C22—H22B	109.1
N2—C6—S2	125.9 (2)	N6—C22—H22B	109.1
N4—C6—S2	125.5 (2)	H22A—C22—H22B	107.9
N3—C7—N2	109.7 (2)	N6—C23—C24	113.0 (3)
N3—C7—C8	112.1 (2)	N6—C23—H23A	109.0
N2—C7—C8	111.5 (2)	C24—C23—H23A	109.0
N3—C7—C14	103.0 (2)	N6—C23—H23B	109.0
N2—C7—C14	102.7 (2)	C24—C23—H23B	109.0
C8—C7—C14	117.1 (2)	H23A—C23—H23B	107.8
C13—C8—C9	118.9 (3)	C23—C24—Cl2	107.7 (2)
C13—C8—C7	120.8 (3)	C23—C24—H24A	110.2
C9—C8—C7	120.3 (3)	Cl2—C24—H24A	110.2
C10—C9—C8	119.8 (4)	C23—C24—H24B	110.2
C10—C9—H9	120.1	Cl2—C24—H24B	110.2
C8—C9—H9	120.1	H24A—C24—H24B	108.5
C11—C10—C9	120.4 (4)	C4—N1—C3	110.6 (3)
C11—C10—H10	119.8	C4—N1—C2	114.7 (3)
C9—C10—H10	119.8	C3—N1—C2	114.1 (3)
C12—C11—C10	120.0 (4)	C6—N2—C7	112.7 (2)
C12—C11—H11	120.0	C6—N2—C4	125.2 (3)
C10—C11—H11	120.0	C7—N2—C4	114.4 (2)
C11—C12—C13	119.7 (4)	C5—N3—C7	112.7 (2)
C11—C12—H12	120.1	C5—N3—C3	124.9 (3)
C13—C12—H12	120.1	C7—N3—C3	115.2 (2)
C8—C13—C12	121.2 (4)	C6—N4—C14	112.0 (2)
C8—C13—H13	119.4	C6—N4—C22	125.0 (3)
C12—C13—H13	119.4	C14—N4—C22	115.1 (2)
N5—C14—N4	109.6 (2)	C5—N5—C14	112.3 (2)
N5—C14—C15	111.8 (2)	C5—N5—C21	124.3 (2)
N4—C14—C15	112.1 (2)	C14—N5—C21	115.0 (2)
N5—C14—C7	102.5 (2)	C21—N6—C23	113.2 (2)
N4—C14—C7	102.9 (2)	C21—N6—C22	108.8 (2)
C15—C14—C7	117.0 (2)	C23—N6—C22	111.1 (3)

Cl1—C1—C2—N1	−63.9 (4)	C8—C7—N2—C6	132.9 (3)
N3—C7—C8—C13	−153.4 (3)	C14—C7—N2—C6	6.7 (3)
N2—C7—C8—C13	−29.9 (4)	N3—C7—N2—C4	48.9 (3)
C14—C7—C8—C13	88.0 (4)	C8—C7—N2—C4	−75.9 (3)
N3—C7—C8—C9	27.4 (4)	C14—C7—N2—C4	157.9 (2)
N2—C7—C8—C9	150.9 (3)	N1—C4—N2—C6	93.6 (3)
C14—C7—C8—C9	−91.2 (3)	N1—C4—N2—C7	−53.5 (3)
C13—C8—C9—C10	−0.4 (5)	N5—C5—N3—C7	10.2 (3)
C7—C8—C9—C10	178.8 (3)	S1—C5—N3—C7	−172.8 (2)
C8—C9—C10—C11	0.1 (6)	N5—C5—N3—C3	158.9 (3)
C9—C10—C11—C12	0.4 (7)	S1—C5—N3—C3	−24.0 (4)
C10—C11—C12—C13	−0.6 (7)	N2—C7—N3—C5	103.0 (3)
C9—C8—C13—C12	0.2 (5)	C8—C7—N3—C5	−132.5 (3)
C7—C8—C13—C12	−179.0 (3)	C14—C7—N3—C5	−5.8 (3)
C11—C12—C13—C8	0.3 (6)	N2—C7—N3—C3	−48.9 (3)
N3—C7—C14—N5	−0.4 (3)	C8—C7—N3—C3	75.5 (3)
N2—C7—C14—N5	−114.4 (2)	C14—C7—N3—C3	−157.8 (2)
C8—C7—C14—N5	123.1 (3)	N1—C3—N3—C5	−95.3 (3)
N3—C7—C14—N4	113.5 (2)	N1—C3—N3—C7	52.8 (3)
N2—C7—C14—N4	−0.6 (3)	N2—C6—N4—C14	10.1 (3)
C8—C7—C14—N4	−123.1 (3)	S2—C6—N4—C14	−172.8 (2)
N3—C7—C14—C15	−123.1 (3)	N2—C6—N4—C22	157.3 (2)
N2—C7—C14—C15	122.9 (3)	S2—C6—N4—C22	−25.5 (4)
C8—C7—C14—C15	0.3 (4)	N5—C14—N4—C6	102.9 (3)
N5—C14—C15—C20	151.7 (3)	C15—C14—N4—C6	−132.2 (3)
N4—C14—C15—C20	28.1 (4)	C7—C14—N4—C6	−5.6 (3)
C7—C14—C15—C20	−90.5 (3)	N5—C14—N4—C22	−47.8 (3)
N5—C14—C15—C16	−30.2 (4)	C15—C14—N4—C22	77.1 (3)
N4—C14—C15—C16	−153.9 (3)	C7—C14—N4—C22	−156.4 (2)
C7—C14—C15—C16	87.5 (4)	N6—C22—N4—C6	−92.4 (3)
C20—C15—C16—C17	−0.5 (5)	N6—C22—N4—C14	54.0 (3)
C14—C15—C16—C17	−178.6 (3)	N3—C5—N5—C14	−10.4 (3)
C15—C16—C17—C18	−0.3 (6)	S1—C5—N5—C14	172.6 (2)
C16—C17—C18—C19	1.1 (7)	N3—C5—N5—C21	−156.7 (3)
C17—C18—C19—C20	−1.0 (7)	S1—C5—N5—C21	26.3 (4)
C16—C15—C20—C19	0.7 (5)	N4—C14—N5—C5	−102.4 (3)
C14—C15—C20—C19	178.7 (3)	C15—C14—N5—C5	132.6 (3)
C18—C19—C20—C15	0.1 (7)	C7—C14—N5—C5	6.5 (3)
N6—C23—C24—Cl2	171.8 (2)	N4—C14—N5—C21	47.2 (3)
N2—C4—N1—C3	54.4 (3)	C15—C14—N5—C21	−77.8 (3)
N2—C4—N1—C2	−76.3 (3)	C7—C14—N5—C21	156.1 (2)
N3—C3—N1—C4	−53.6 (3)	N6—C21—N5—C5	92.0 (3)
N3—C3—N1—C2	77.5 (3)	N6—C21—N5—C14	−53.5 (3)
C1—C2—N1—C4	−77.7 (4)	N5—C21—N6—C23	−68.8 (3)
C1—C2—N1—C3	153.3 (3)	N5—C21—N6—C22	55.2 (3)
N4—C6—N2—C7	−10.6 (3)	C24—C23—N6—C21	−71.7 (3)
S2—C6—N2—C7	172.3 (2)	C24—C23—N6—C22	165.6 (2)
N4—C6—N2—C4	−158.2 (3)	N4—C22—N6—C21	−55.4 (3)
S2—C6—N2—C4	24.7 (4)	N4—C22—N6—C23	69.9 (3)
N3—C7—N2—C6	−102.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C24—H24B···N1ⁱ	0.97	2.55	3.485 (4)	162
C22—H22B···S1ⁱⁱ	0.97	2.80	3.607 (3)	141

Symmetry codes: (i) x−1, y, z; (ii) −x, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₆Cl₂N₆S₂
M_r	533.53
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	8.7566 (2), 14.0877 (3), 20.8575 (5)
β (°)	99.525 (1)
V (Å³)	2537.52 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.45
Crystal size (mm)	0.23 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART 4K CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	16129, 4979, 3375
R_int	0.078
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.064, 0.164, 1.02
No. of reflections	4979
No. of parameters	307
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.51

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
C24—H24B···N1ⁱ	0.97	2.55	3.485 (4)	161.8
C22—H22B···S1ⁱⁱ	0.97	2.80	3.607 (3)	141.4

Symmetry codes: (i) x−1, y, z; (ii) −x, y+1/2, −z+1/2.

Acknowledgements

The authors thank Professor An-Xin Wu for technical assistance and Dr Meng Xiang-Gao for the data collection.

References

Bruker (1997). SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (1999). SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ramos, S. & Rosen, W. (1981). J. Org. Chem. 46, 3530–3533. CrossRef CAS Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wang, Z. & Xi, H. (2009). Acta Cryst. E65, o1426. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wu, A., Chakraborty, A., Witl, D., Lagona, J., Damkaci, F., Ofori, M. A., Chiles, J. K., Fettinger, J. C. & Isaacs, L. (2002). J. Org. Chem. 67, 5817–5830. Web of Science CSD CrossRef PubMed CAS Google Scholar

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Volume 65| Part 7| July 2009| Page o1715

doi:10.1107/S1600536809024118

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

2,6-Bis(2-chloro­ethyl)-8b,8c-di­phenyl­perhydro-2,3a,4a,6,7a,8a-hexa­aza­cyclo­penta­[def]fluorene-4,8-di­thione

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2,6-Bis(2-chloroethyl)-8b,8c-diphenylperhydro-2,3a,4a,6,7a,8a-hexaazacyclopenta[def]fluorene-4,8-dithione