2,6-Bis(2-hydroxy-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(28)N(6)O(2)S(2), the dihedral angle between the aromatic ring planes is 42.2 (1)°. In the crystal structure, the hydr-oxy groups are involved in O-H⋯S hydrogen bonding, which links the mol-ecules 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 = 496.64

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.141

S = 1.04

5248 reflections

313 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.43 e Å−3

Δρmin = −0.31 e Å−3

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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809019230/cv2558sup1.cif

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

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

C24H28N6O2S2	F(000) = 1048
Mr = 496.64	Dx = 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

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

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(Fo2) + (0.086P)2] where P = (Fo2 + 2Fc2)/3
5248 reflections	(Δ/σ)max < 0.001
313 parameters	Δρmax = 0.43 e Å−3
2 restraints	Δρmin = −0.31 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	−0.12009 (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)

	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)

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)

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)

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) ; (ii) .