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

Wang, Z.; Xi, H.

doi:10.1107/S1600536809019230

organic compounds

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ISSN: 2056-9890

Volume 65| Part 6| June 2009| Page o1426

doi:10.1107/S1600536809019230

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

Zihua Wang ^a ^* and Hailing Xi ^b

^aKey Laboratory of Pesticide and Chemical Biology of the Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China, and ^b6th Department, Research Institute of Chemical Defence, Beijing 102205, People's Republic of China
^*Correspondence e-mail: wangzihua@mails.ccnu.edu.cn

(Received 24 April 2009; accepted 21 May 2009; online 29 May 2009)

In the title molecule, C₂₄H₂₈N₆O₂S₂, the dihedral angle between the aromatic ring planes is 42.2 (1)°. In the crystal structure, the hydroxy groups are involved in O—H⋯S hydrogen bonding, which links the molecules into corrugated layers propagating parallel to the bc plane.

Related literature

For the preparation of the title compound, see: Li et al. (2006 ); Broan et al. (1989 ). For general background regarding glycoluril and its derivatives, see Gao et al. (2009 ).

Experimental

Crystal data

C₂₄H₂₈N₆O₂S₂
M_r = 496.64
Monoclinic, P 2₁ /c
a = 10.8207 (3) Å
b = 11.9259 (3) Å
c = 18.7222 (5) Å
β = 95.917 (1)°
V = 2403.16 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.26 mm⁻¹
T = 295 K
0.30 × 0.20 × 0.10 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick,1996 ) T_min = 0.927, T_max = 0.975
26638 measured reflections
5248 independent reflections
3908 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.049
wR(F²) = 0.141
S = 1.04
5248 reflections
313 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.43 e Å⁻³
Δρ_min = −0.31 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯S2ⁱ	0.81 (2)	2.605 (19)	3.337 (2)	151 (3)
O2—H2⋯S2ⁱⁱ	0.83 (2)	2.599 (14)	3.409 (2)	165 (4)
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x, -y+1, -z.

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); 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 global, I. DOI: 10.1107/S1600536809019230/cv2558sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809019230/cv2558Isup2.hkl

checkCIF report

Comment top

The rigid concave shape of glycoluril makes it a versatile building block to construct various supramolecular objects (Gao et al., 2009). We report here the structure of the title thioglycoluril derivative (Fig. 1), which is a potential receptor in supramolecular chemistry.

The title compound, C₂₄H₂₈N₆O₂S₂, is a thioglycoluril derivative. The crystal packing is stabilized by intermolecular O–H···S hydrogen bonds (Table 1).

Related literature top

For the preparation of the title compound, see: Li et al. (2006); Broan et al. (1989). For general background regarding glycoluril and its derivatives, see Gao et al. (2009).

Experimental top

The title compound was synthesized according to the procedure reported (Broan et al., 1989; Li et al., 2006). 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, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.

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

Crystal data top

C₂₄H₂₈N₆O₂S₂	F(000) = 1048
M_r = 496.64	D_x = 1.373 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7811 reflections
a = 10.8207 (3) Å	θ = 2.6–26.8°
b = 11.9259 (3) Å	µ = 0.26 mm⁻¹
c = 18.7222 (5) Å	T = 295 K
β = 95.917 (1)°	Block, colorless
V = 2403.16 (11) Å³	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5248 independent reflections
Radiation source: fine-focus sealed tube	3908 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
ϕ and ω scans	θ_max = 27.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick,1996)	h = −13→13
T_min = 0.927, T_max = 0.975	k = −15→14
26638 measured reflections	l = −23→23

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.086P)²] where P = (F_o² + 2F_c²)/3
5248 reflections	(Δ/σ)_max < 0.001
313 parameters	Δρ_max = 0.43 e Å⁻³
2 restraints	Δρ_min = −0.31 e Å⁻³

Crystal data top

C₂₄H₂₈N₆O₂S₂	V = 2403.16 (11) Å³
M_r = 496.64	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.8207 (3) Å	µ = 0.26 mm⁻¹
b = 11.9259 (3) Å	T = 295 K
c = 18.7222 (5) Å	0.30 × 0.20 × 0.10 mm
β = 95.917 (1)°

Data collection top

Bruker SMART APEX CCD area-detector diffractometer	5248 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick,1996)	3908 reflections with I > 2σ(I)
T_min = 0.927, T_max = 0.975	R_int = 0.048
26638 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.049	2 restraints
wR(F²) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.43 e Å⁻³
5248 reflections	Δρ_min = −0.31 e Å⁻³
313 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	−0.12009 (19)	0.06722 (19)	0.17347 (12)	0.0556 (6)
H1A	−0.1247	0.1295	0.2064	0.067*
H1B	−0.1835	0.0784	0.1336	0.067*
C2	0.00508 (18)	0.06743 (18)	0.14581 (10)	0.0468 (5)
H2A	0.0141	0.0001	0.1177	0.056*
H2B	0.0113	0.1316	0.1146	0.056*
C3	0.22092 (19)	0.02137 (15)	0.18881 (10)	0.0423 (5)
H3A	0.2027	−0.0508	0.1663	0.051*
H3B	0.2735	0.0084	0.2332	0.051*
C4	0.12806 (17)	0.18506 (15)	0.23345 (9)	0.0389 (4)
H4A	0.1770	0.1812	0.2798	0.047*
H4B	0.0491	0.2199	0.2403	0.047*
C5	0.27962 (17)	0.08201 (15)	0.06750 (10)	0.0376 (4)
C6	0.14142 (15)	0.32561 (14)	0.13366 (9)	0.0322 (4)
C7	0.31088 (15)	0.20650 (13)	0.16475 (9)	0.0302 (4)
C8	0.41469 (15)	0.21794 (15)	0.22511 (9)	0.0350 (4)
C9	0.51836 (17)	0.14859 (17)	0.22663 (11)	0.0459 (5)
H9	0.5209	0.0914	0.1930	0.055*
C10	0.61795 (18)	0.1651 (2)	0.27853 (13)	0.0579 (6)
H10	0.6882	0.1201	0.2790	0.070*
C11	0.6129 (2)	0.2475 (2)	0.32904 (13)	0.0617 (6)
H11	0.6794	0.2575	0.3641	0.074*
C12	0.5107 (2)	0.31542 (19)	0.32845 (12)	0.0566 (6)
H12	0.5079	0.3709	0.3632	0.068*
C13	0.41094 (18)	0.30164 (16)	0.27611 (10)	0.0428 (4)
H13	0.3420	0.3484	0.2754	0.051*
C14	0.32978 (15)	0.26964 (13)	0.09338 (9)	0.0318 (4)
C15	0.45229 (15)	0.33084 (15)	0.09195 (9)	0.0354 (4)
C16	0.55620 (18)	0.27555 (18)	0.07309 (12)	0.0510 (5)
H16	0.5494	0.2025	0.0557	0.061*
C17	0.67082 (19)	0.3290 (2)	0.08007 (13)	0.0599 (6)
H17	0.7408	0.2914	0.0676	0.072*
C18	0.68142 (19)	0.4367 (2)	0.10520 (13)	0.0577 (6)
H18	0.7589	0.4712	0.1107	0.069*
C19	0.5778 (2)	0.49443 (19)	0.12239 (12)	0.0523 (5)
H19	0.5848	0.5682	0.1384	0.063*
C20	0.46311 (17)	0.44085 (16)	0.11538 (11)	0.0441 (5)
H20	0.3929	0.4793	0.1266	0.053*
C21	0.28287 (19)	0.22150 (17)	−0.03467 (10)	0.0464 (5)
H21A	0.3540	0.2611	−0.0498	0.056*
H21B	0.2662	0.1576	−0.0663	0.056*
C22	0.19164 (19)	0.38613 (15)	0.01067 (11)	0.0428 (5)
H22A	0.1156	0.4296	0.0086	0.051*
H22B	0.2573	0.4354	−0.0019	0.051*
C23	0.0576 (2)	0.23381 (17)	−0.04220 (12)	0.0537 (6)
H23A	0.0491	0.2073	0.0060	0.064*
H23B	0.0610	0.1686	−0.0729	0.064*
C24	−0.0547 (2)	0.3012 (2)	−0.06773 (14)	0.0681 (7)
H24A	−0.1281	0.2574	−0.0610	0.082*
H24B	−0.0563	0.3676	−0.0379	0.082*
N1	0.10632 (14)	0.07216 (13)	0.20529 (8)	0.0414 (4)
N2	0.28966 (13)	0.09106 (11)	0.14054 (8)	0.0342 (3)
N3	0.19398 (12)	0.25404 (12)	0.18405 (7)	0.0319 (3)
N4	0.31342 (14)	0.18107 (12)	0.03940 (8)	0.0373 (4)
N5	0.22274 (13)	0.34526 (12)	0.08454 (8)	0.0333 (3)
N6	0.17545 (15)	0.29589 (13)	−0.04166 (8)	0.0453 (4)
O1	−0.14482 (17)	−0.03208 (18)	0.20862 (11)	0.0846 (6)
H1	−0.087 (2)	−0.045 (3)	0.2388 (15)	0.127*
O2	−0.0615 (2)	0.33480 (17)	−0.13943 (11)	0.0862 (6)
H2	−0.033 (3)	0.3995 (15)	−0.1335 (19)	0.129*
S1	0.24080 (7)	−0.03339 (4)	0.02083 (3)	0.0601 (2)
S2	0.00120 (4)	0.38457 (5)	0.13406 (3)	0.04925 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0446 (12)	0.0720 (15)	0.0484 (13)	−0.0162 (11)	−0.0034 (10)	0.0076 (11)
C2	0.0515 (12)	0.0500 (12)	0.0384 (11)	−0.0192 (9)	0.0022 (9)	−0.0006 (9)
C3	0.0530 (11)	0.0342 (10)	0.0391 (11)	−0.0063 (8)	0.0023 (9)	0.0039 (8)
C4	0.0369 (10)	0.0488 (11)	0.0313 (10)	−0.0088 (8)	0.0051 (8)	−0.0008 (8)
C5	0.0393 (10)	0.0346 (9)	0.0388 (11)	0.0028 (8)	0.0031 (8)	−0.0017 (8)
C6	0.0281 (8)	0.0316 (9)	0.0361 (10)	−0.0041 (7)	−0.0006 (7)	−0.0059 (7)
C7	0.0279 (8)	0.0303 (8)	0.0323 (9)	0.0002 (6)	0.0028 (7)	−0.0009 (7)
C8	0.0301 (9)	0.0389 (10)	0.0354 (10)	−0.0043 (7)	0.0008 (7)	0.0055 (8)
C9	0.0360 (10)	0.0533 (12)	0.0481 (12)	0.0027 (9)	0.0033 (9)	0.0075 (9)
C10	0.0316 (10)	0.0721 (15)	0.0688 (16)	0.0026 (10)	−0.0008 (10)	0.0249 (13)
C11	0.0438 (13)	0.0765 (16)	0.0600 (15)	−0.0198 (11)	−0.0178 (11)	0.0157 (13)
C12	0.0595 (14)	0.0585 (13)	0.0485 (13)	−0.0183 (11)	−0.0109 (10)	−0.0011 (10)
C13	0.0429 (10)	0.0417 (10)	0.0422 (11)	−0.0050 (8)	−0.0029 (8)	−0.0009 (8)
C14	0.0312 (9)	0.0308 (9)	0.0334 (9)	0.0007 (7)	0.0041 (7)	−0.0024 (7)
C15	0.0308 (9)	0.0414 (10)	0.0345 (10)	−0.0021 (7)	0.0062 (7)	0.0051 (8)
C16	0.0398 (11)	0.0517 (12)	0.0636 (14)	0.0056 (9)	0.0155 (10)	0.0069 (10)
C17	0.0328 (11)	0.0704 (15)	0.0789 (17)	0.0057 (10)	0.0174 (10)	0.0173 (13)
C18	0.0323 (10)	0.0753 (16)	0.0647 (15)	−0.0137 (10)	0.0008 (10)	0.0233 (12)
C19	0.0448 (11)	0.0550 (12)	0.0564 (13)	−0.0150 (10)	0.0016 (9)	0.0039 (10)
C20	0.0344 (10)	0.0466 (11)	0.0513 (12)	−0.0054 (8)	0.0050 (8)	−0.0008 (9)
C21	0.0574 (13)	0.0478 (11)	0.0348 (11)	−0.0032 (9)	0.0079 (9)	−0.0012 (9)
C22	0.0426 (10)	0.0369 (10)	0.0479 (12)	−0.0023 (8)	−0.0005 (9)	0.0099 (9)
C23	0.0595 (14)	0.0503 (12)	0.0481 (13)	−0.0145 (10)	−0.0098 (10)	0.0072 (10)
C24	0.0584 (15)	0.0822 (17)	0.0611 (16)	−0.0197 (13)	−0.0068 (12)	0.0089 (13)
N1	0.0435 (9)	0.0430 (9)	0.0375 (9)	−0.0118 (7)	0.0032 (7)	0.0011 (7)
N2	0.0400 (8)	0.0283 (7)	0.0341 (8)	−0.0022 (6)	0.0027 (6)	−0.0023 (6)
N3	0.0258 (7)	0.0364 (8)	0.0337 (8)	−0.0021 (6)	0.0043 (6)	−0.0027 (6)
N4	0.0446 (9)	0.0356 (8)	0.0323 (8)	−0.0011 (7)	0.0062 (7)	−0.0035 (6)
N5	0.0281 (7)	0.0341 (8)	0.0374 (8)	0.0006 (6)	0.0011 (6)	0.0034 (6)
N6	0.0508 (10)	0.0446 (9)	0.0390 (9)	−0.0074 (7)	−0.0022 (7)	0.0054 (7)
O1	0.0646 (12)	0.1027 (14)	0.0842 (14)	−0.0396 (11)	−0.0034 (9)	0.0390 (11)
O2	0.0899 (14)	0.0982 (15)	0.0647 (12)	−0.0084 (12)	−0.0198 (10)	0.0193 (11)
S1	0.0926 (5)	0.0386 (3)	0.0479 (4)	−0.0061 (3)	0.0013 (3)	−0.0121 (2)
S2	0.0294 (3)	0.0545 (3)	0.0636 (4)	0.0086 (2)	0.0036 (2)	−0.0030 (3)

Geometric parameters (Å, º) top

C1—O1	1.394 (3)	C12—H12	0.9300
C1—C2	1.499 (3)	C13—H13	0.9300
C1—H1A	0.9700	C14—N4	1.460 (2)
C1—H1B	0.9700	C14—N5	1.464 (2)
C2—N1	1.481 (3)	C14—C15	1.516 (2)
C2—H2A	0.9700	C15—C16	1.380 (2)
C2—H2B	0.9700	C15—C20	1.384 (3)
C3—N1	1.442 (2)	C16—C17	1.388 (3)
C3—N2	1.483 (2)	C16—H16	0.9300
C3—H3A	0.9700	C17—C18	1.369 (3)
C3—H3B	0.9700	C17—H17	0.9300
C4—N1	1.456 (2)	C18—C19	1.381 (3)
C4—N3	1.476 (2)	C18—H18	0.9300
C4—H4A	0.9700	C19—C20	1.390 (3)
C4—H4B	0.9700	C19—H19	0.9300
C5—N4	1.359 (2)	C20—H20	0.9300
C5—N2	1.365 (2)	C21—N6	1.457 (2)
C5—S1	1.6609 (19)	C21—N4	1.473 (2)
C6—N3	1.353 (2)	C21—H21A	0.9700
C6—N5	1.357 (2)	C21—H21B	0.9700
C6—S2	1.6730 (17)	C22—N6	1.454 (2)
C7—N2	1.460 (2)	C22—N5	1.472 (2)
C7—N3	1.465 (2)	C22—H22A	0.9700
C7—C8	1.515 (2)	C22—H22B	0.9700
C7—C14	1.565 (2)	C23—N6	1.474 (2)
C8—C13	1.385 (3)	C23—C24	1.494 (3)
C8—C9	1.392 (3)	C23—H23A	0.9700
C9—C10	1.389 (3)	C23—H23B	0.9700
C9—H9	0.9300	C24—O2	1.395 (3)
C10—C11	1.369 (3)	C24—H24A	0.9700
C10—H10	0.9300	C24—H24B	0.9700
C11—C12	1.370 (3)	O1—H1	0.81 (2)
C11—H11	0.9300	O2—H2	0.83 (2)
C12—C13	1.390 (3)

O1—C1—C2	112.9 (2)	C16—C15—C14	120.75 (16)
O1—C1—H1A	109.0	C20—C15—C14	119.75 (15)
C2—C1—H1A	109.0	C15—C16—C17	120.0 (2)
O1—C1—H1B	109.0	C15—C16—H16	120.0
C2—C1—H1B	109.0	C17—C16—H16	120.0
H1A—C1—H1B	107.8	C18—C17—C16	120.3 (2)
N1—C2—C1	111.41 (16)	C18—C17—H17	119.8
N1—C2—H2A	109.3	C16—C17—H17	119.8
C1—C2—H2A	109.3	C17—C18—C19	120.44 (19)
N1—C2—H2B	109.3	C17—C18—H18	119.8
C1—C2—H2B	109.3	C19—C18—H18	119.8
H2A—C2—H2B	108.0	C18—C19—C20	119.1 (2)
N1—C3—N2	113.05 (14)	C18—C19—H19	120.4
N1—C3—H3A	109.0	C20—C19—H19	120.4
N2—C3—H3A	109.0	C15—C20—C19	120.72 (19)
N1—C3—H3B	109.0	C15—C20—H20	119.6
N2—C3—H3B	109.0	C19—C20—H20	119.6
H3A—C3—H3B	107.8	N6—C21—N4	112.54 (15)
N1—C4—N3	111.04 (13)	N6—C21—H21A	109.1
N1—C4—H4A	109.4	N4—C21—H21A	109.1
N3—C4—H4A	109.4	N6—C21—H21B	109.1
N1—C4—H4B	109.4	N4—C21—H21B	109.1
N3—C4—H4B	109.4	H21A—C21—H21B	107.8
H4A—C4—H4B	108.0	N6—C22—N5	112.82 (14)
N4—C5—N2	108.81 (15)	N6—C22—H22A	109.0
N4—C5—S1	125.48 (14)	N5—C22—H22A	109.0
N2—C5—S1	125.61 (14)	N6—C22—H22B	109.0
N3—C6—N5	109.03 (14)	N5—C22—H22B	109.0
N3—C6—S2	125.32 (13)	H22A—C22—H22B	107.8
N5—C6—S2	125.60 (13)	N6—C23—C24	113.98 (18)
N2—C7—N3	109.23 (13)	N6—C23—H23A	108.8
N2—C7—C8	113.40 (14)	C24—C23—H23A	108.8
N3—C7—C8	111.95 (13)	N6—C23—H23B	108.8
N2—C7—C14	102.63 (13)	C24—C23—H23B	108.8
N3—C7—C14	102.50 (13)	H23A—C23—H23B	107.7
C8—C7—C14	116.19 (13)	O2—C24—C23	115.0 (2)
C13—C8—C9	119.68 (17)	O2—C24—H24A	108.5
C13—C8—C7	120.47 (16)	C23—C24—H24A	108.5
C9—C8—C7	119.72 (16)	O2—C24—H24B	108.5
C10—C9—C8	119.7 (2)	C23—C24—H24B	108.5
C10—C9—H9	120.1	H24A—C24—H24B	107.5
C8—C9—H9	120.1	C3—N1—C4	110.83 (14)
C11—C10—C9	120.1 (2)	C3—N1—C2	114.15 (15)
C11—C10—H10	119.9	C4—N1—C2	112.76 (15)
C9—C10—H10	119.9	C5—N2—C7	112.29 (14)
C10—C11—C12	120.6 (2)	C5—N2—C3	124.97 (15)
C10—C11—H11	119.7	C7—N2—C3	114.32 (13)
C12—C11—H11	119.7	C6—N3—C7	112.56 (13)
C11—C12—C13	120.2 (2)	C6—N3—C4	126.37 (14)
C11—C12—H12	119.9	C7—N3—C4	115.11 (13)
C13—C12—H12	119.9	C5—N4—C14	112.29 (14)
C8—C13—C12	119.69 (19)	C5—N4—C21	127.29 (15)
C8—C13—H13	120.2	C14—N4—C21	114.47 (14)
C12—C13—H13	120.2	C6—N5—C14	112.19 (14)
N4—C14—N5	109.23 (14)	C6—N5—C22	126.32 (14)
N4—C14—C15	112.33 (13)	C14—N5—C22	114.32 (14)
N5—C14—C15	112.61 (13)	C22—N6—C21	110.52 (15)
N4—C14—C7	103.04 (13)	C22—N6—C23	114.88 (16)
N5—C14—C7	102.79 (12)	C21—N6—C23	112.11 (16)
C15—C14—C7	115.99 (14)	C1—O1—H1	108 (3)
C16—C15—C20	119.29 (17)	C24—O2—H2	99 (3)

O1—C1—C2—N1	−69.4 (2)	C8—C7—N2—C5	−133.09 (15)
N2—C7—C8—C13	−148.92 (15)	C14—C7—N2—C5	−6.95 (17)
N3—C7—C8—C13	−24.8 (2)	N3—C7—N2—C3	−48.59 (19)
C14—C7—C8—C13	92.50 (19)	C8—C7—N2—C3	77.02 (18)
N2—C7—C8—C9	35.3 (2)	C14—C7—N2—C3	−156.84 (14)
N3—C7—C8—C9	159.47 (15)	N1—C3—N2—C5	−93.2 (2)
C14—C7—C8—C9	−83.3 (2)	N1—C3—N2—C7	52.3 (2)
C13—C8—C9—C10	−1.1 (3)	N5—C6—N3—C7	−9.10 (19)
C7—C8—C9—C10	174.74 (17)	S2—C6—N3—C7	173.37 (12)
C8—C9—C10—C11	1.6 (3)	N5—C6—N3—C4	−160.35 (15)
C9—C10—C11—C12	−0.9 (3)	S2—C6—N3—C4	22.1 (2)
C10—C11—C12—C13	−0.4 (3)	N2—C7—N3—C6	−103.97 (15)
C9—C8—C13—C12	−0.2 (3)	C8—C7—N3—C6	129.58 (15)
C7—C8—C13—C12	−175.92 (17)	C14—C7—N3—C6	4.36 (17)
C11—C12—C13—C8	0.9 (3)	N2—C7—N3—C4	50.70 (18)
N2—C7—C14—N4	1.33 (15)	C8—C7—N3—C4	−75.75 (17)
N3—C7—C14—N4	−111.96 (13)	C14—C7—N3—C4	159.04 (13)
C8—C7—C14—N4	125.65 (15)	N1—C4—N3—C6	95.90 (19)
N2—C7—C14—N5	114.86 (13)	N1—C4—N3—C7	−54.72 (19)
N3—C7—C14—N5	1.57 (15)	N2—C5—N4—C14	−9.2 (2)
C8—C7—C14—N5	−120.81 (15)	S1—C5—N4—C14	174.18 (13)
N2—C7—C14—C15	−121.82 (15)	N2—C5—N4—C21	−160.26 (16)
N3—C7—C14—C15	124.89 (14)	S1—C5—N4—C21	23.2 (3)
C8—C7—C14—C15	2.5 (2)	N5—C14—N4—C5	−104.12 (16)
N4—C14—C15—C16	−32.1 (2)	C15—C14—N4—C5	130.19 (16)
N5—C14—C15—C16	−155.98 (17)	C7—C14—N4—C5	4.64 (18)
C7—C14—C15—C16	86.0 (2)	N5—C14—N4—C21	50.83 (18)
N4—C14—C15—C20	153.17 (17)	C15—C14—N4—C21	−74.86 (18)
N5—C14—C15—C20	29.3 (2)	C7—C14—N4—C21	159.59 (14)
C7—C14—C15—C20	−88.7 (2)	N6—C21—N4—C5	96.9 (2)
C20—C15—C16—C17	2.2 (3)	N6—C21—N4—C14	−53.6 (2)
C14—C15—C16—C17	−172.49 (19)	N3—C6—N5—C14	10.25 (19)
C15—C16—C17—C18	−0.4 (3)	S2—C6—N5—C14	−172.23 (12)
C16—C17—C18—C19	−1.5 (4)	N3—C6—N5—C22	158.67 (15)
C17—C18—C19—C20	1.5 (3)	S2—C6—N5—C22	−23.8 (2)
C16—C15—C20—C19	−2.2 (3)	N4—C14—N5—C6	101.81 (16)
C14—C15—C20—C19	172.53 (18)	C15—C14—N5—C6	−132.65 (15)
C18—C19—C20—C15	0.4 (3)	C7—C14—N5—C6	−7.11 (17)
N6—C23—C24—O2	65.1 (3)	N4—C14—N5—C22	−50.61 (18)
N2—C3—N1—C4	−53.7 (2)	C15—C14—N5—C22	74.93 (18)
N2—C3—N1—C2	74.92 (19)	C7—C14—N5—C22	−159.53 (13)
N3—C4—N1—C3	54.3 (2)	N6—C22—N5—C6	−94.4 (2)
N3—C4—N1—C2	−75.12 (18)	N6—C22—N5—C14	53.41 (19)
C1—C2—N1—C3	152.21 (17)	N5—C22—N6—C21	−52.6 (2)
C1—C2—N1—C4	−80.1 (2)	N5—C22—N6—C23	75.5 (2)
N4—C5—N2—C7	10.2 (2)	N4—C21—N6—C22	52.5 (2)
S1—C5—N2—C7	−173.19 (13)	N4—C21—N6—C23	−77.0 (2)
N4—C5—N2—C3	156.33 (16)	C24—C23—N6—C22	67.6 (2)
S1—C5—N2—C3	−27.1 (3)	C24—C23—N6—C21	−165.17 (18)
N3—C7—N2—C5	101.30 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···S2ⁱ	0.81 (2)	2.61 (2)	3.337 (2)	151 (3)
O2—H2···S2ⁱⁱ	0.83 (2)	2.60 (1)	3.409 (2)	165 (4)

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

Experimental details

Crystal data
Chemical formula	C₂₄H₂₈N₆O₂S₂
M_r	496.64
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	10.8207 (3), 11.9259 (3), 18.7222 (5)
β (°)	95.917 (1)
V (Å³)	2403.16 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick,1996)
T_min, T_max	0.927, 0.975
No. of measured, independent and observed [I > 2σ(I)] reflections	26638, 5248, 3908
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.049, 0.141, 1.04
No. of reflections	5248
No. of parameters	313
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.43, −0.31

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), 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
O1—H1···S2ⁱ	0.81 (2)	2.605 (19)	3.337 (2)	151 (3)
O2—H2···S2ⁱⁱ	0.83 (2)	2.599 (14)	3.409 (2)	165 (4)

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

Acknowledgements

The authors thank Professor An-Xin Wu for technical assistance and Dr Xiang-Gao Meng for the 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 (2001). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Gao, M., Cao, L., Wang, Z., Sun, J., She, N. & Wu, A. (2009). Synlett, pp. 315–319. Google Scholar
Li, Y., Yin, G., Guo, H., Zhou, B. & Wu, A. (2006). Synthesis, pp. 2897–2902. Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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

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