2,6-Bis(2-chloro-ethyl)-8b,8c-diphenyl-perhydro-2,3a,4a,6,7a,8a-hexa-azacyclo-penta-[def]fluorene-4,8-dithione.

In the title mol-ecule, C(24)H(26)Cl(2)N(6)S(2), 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 inter-molecular 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 = 533.53

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.064

wR(F 2) = 0.164

S = 1.02

4979 reflections

307 parameters

H-atom parameters constrained

Δρmax = 0.63 e Å−3

Δρmin = −0.51 e Å−3

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.

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

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

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

C24H26Cl2N6S2	F(000) = 1112
Mr = 533.53	Dx = 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

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

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(Fo2) + (0.0798P)2] where P = (Fo2 + 2Fc2)/3
4979 reflections	(Δ/σ)max < 0.001
307 parameters	Δρmax = 0.63 e Å−3
0 restraints	Δρmin = −0.51 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) ; (ii) .