5-Anilino-3-benzyl-sulfanyl-6-(3-chloro-anilino)-1-phenyl-1H-pyrazolo-[3,4-d]pyrimidin-4(5H)-one.

In the title compound, C(30)H(23)ClN(6)OS, the benzyl, the 3-chloro-anilino, the phenyl and the anilino groups form dihedral angles of 85.95 (6), 29.63 (7), 28.55 (1) and 87.48 (6)°, respectively, with the pyrazolo-[3,4-d]pyrimidine unit [maximum deviation = 0.052 (2) Å]. An intra-molecular N-H⋯N hydrogen bond occurs. The crystal structure features N-H⋯O hydrogen bonds.

Related literature

For similar compounds, see: Wang et al. (2004 ▶, 2008 ▶). For their applications, see: Bendich et al. (1954 ▶); Ballell et al. (2007 ▶); Holla et al. (2006 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C30H23ClN6OS

M = 551.05

Triclinic,

a = 10.881 (5) Å

b = 10.948 (4) Å

c = 12.496 (5) Å

α = 103.824 (7)°

β = 109.725 (7)°

γ = 93.377 (7)°

V = 1344.7 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.26 mm−1

T = 293 K

0.42 × 0.40 × 0.36 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker 2000 ▶) T min = 0.771, T max = 1.000

7799 measured reflections

5440 independent reflections

3418 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.114

S = 1.01

5440 reflections

360 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.40 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); 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 and Mercury (Macrae et al., 2008 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812037683/rn2104sup1.cif

Supplementary material file. DOI: 10.1107/S1600536812037683/rn2104Isup2.mol

Supplementary material file. DOI: 10.1107/S1600536812037683/rn2104Isup3.mol

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812037683/rn2104Isup4.hkl

Supplementary material file. DOI: 10.1107/S1600536812037683/rn2104Isup5.cml

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

C30H23ClN6OS	Z = 2
Mr = 551.05	F(000) = 572
Triclinic, P1	Dx = 1.361 Mg m−3
a = 10.881 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.948 (4) Å	Cell parameters from 809 reflections
c = 12.496 (5) Å	θ = 2.6–25.6°
α = 103.824 (7)°	µ = 0.26 mm−1
β = 109.725 (7)°	T = 293 K
γ = 93.377 (7)°	Block, white
V = 1344.7 (9) Å3	0.42 × 0.40 × 0.36 mm

Bruker SMART CCD area-detector diffractometer	5440 independent reflections
Radiation source: fine-focus sealed tube	3418 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.022
phi and ω scans	θmax = 26.4°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker 2000)	h = −13→9
Tmin = 0.771, Tmax = 1.000	k = −13→13
7799 measured reflections	l = −9→15

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ2(Fo2) + (0.0437P)2 + 0.3561P] where P = (Fo2 + 2Fc2)/3
5440 reflections	(Δ/σ)max = 0.001
360 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.40 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
Cl1	0.58922 (10)	−0.29645 (7)	−0.00499 (9)	0.0950 (3)
S1	0.84719 (7)	0.64314 (5)	0.33369 (6)	0.0557 (2)
N1	0.7368 (2)	0.41189 (16)	0.32750 (16)	0.0462 (5)
N2	0.71298 (19)	0.28629 (16)	0.25760 (16)	0.0422 (5)
N3	0.75420 (19)	0.16942 (15)	0.08617 (15)	0.0395 (4)
N4	0.84282 (18)	0.30693 (15)	0.00045 (15)	0.0359 (4)
N5	0.8107 (2)	0.08909 (17)	−0.07736 (18)	0.0448 (5)
H5	0.844 (2)	0.108 (2)	−0.119 (2)	0.045 (7)*
N6	0.8716 (2)	0.31275 (17)	−0.10020 (17)	0.0382 (5)
H6	0.944 (2)	0.354 (2)	−0.0795 (18)	0.034 (6)*
O1	0.89538 (16)	0.52346 (13)	0.07639 (13)	0.0454 (4)
C1	0.7947 (2)	0.47893 (19)	0.27824 (19)	0.0417 (5)
C2	0.8102 (2)	0.40058 (18)	0.17656 (18)	0.0374 (5)
C3	0.7579 (2)	0.27820 (19)	0.16756 (18)	0.0371 (5)
C4	0.8006 (2)	0.18745 (18)	0.00674 (18)	0.0359 (5)
C5	0.8535 (2)	0.42237 (19)	0.08658 (18)	0.0360 (5)
C6	0.8389 (3)	0.6721 (2)	0.4802 (2)	0.0571 (7)
H6A	0.7510	0.6403	0.4744	0.068*
H6B	0.9018	0.6285	0.5272	0.068*
C7	0.8708 (2)	0.8136 (2)	0.5377 (2)	0.0438 (6)
C8	0.7750 (3)	0.8901 (2)	0.5120 (2)	0.0568 (7)
H8	0.6906	0.8537	0.4584	0.068*
C9	0.8016 (3)	1.0192 (3)	0.5641 (3)	0.0661 (8)
H9	0.7353	1.0691	0.5462	0.079*
C10	0.9247 (3)	1.0737 (3)	0.6416 (3)	0.0691 (8)
H10	0.9423	1.1608	0.6779	0.083*
C11	1.0216 (3)	1.0016 (3)	0.6661 (3)	0.0770 (9)
H11	1.1063	1.0395	0.7181	0.092*
C12	0.9953 (3)	0.8704 (3)	0.6138 (2)	0.0655 (8)
H12	1.0626	0.8214	0.6307	0.079*
C13	0.6338 (2)	0.1923 (2)	0.27856 (19)	0.0421 (5)
C14	0.5503 (3)	0.2301 (2)	0.3367 (2)	0.0567 (7)
H14	0.5454	0.3160	0.3624	0.068*
C15	0.4731 (3)	0.1394 (3)	0.3569 (2)	0.0700 (8)
H15	0.4168	0.1650	0.3969	0.084*
C16	0.4787 (3)	0.0121 (3)	0.3187 (2)	0.0657 (8)
H16	0.4275	−0.0482	0.3335	0.079*
C17	0.5606 (3)	−0.0250 (2)	0.2585 (2)	0.0613 (7)
H17	0.5632	−0.1112	0.2306	0.074*
C18	0.6397 (3)	0.0644 (2)	0.2385 (2)	0.0537 (6)
H18	0.6962	0.0386	0.1986	0.064*
C19	0.7924 (2)	−0.04243 (19)	−0.08586 (19)	0.0414 (5)
C20	0.7077 (3)	−0.0968 (2)	−0.0437 (2)	0.0488 (6)
H20	0.6589	−0.0476	−0.0069	0.059*
C21	0.6971 (3)	−0.2271 (2)	−0.0578 (2)	0.0554 (7)
C22	0.7651 (3)	−0.3030 (2)	−0.1140 (2)	0.0629 (8)
H22	0.7567	−0.3900	−0.1219	0.075*
C23	0.8462 (3)	−0.2473 (2)	−0.1585 (2)	0.0628 (7)
H23	0.8912	−0.2978	−0.1989	0.075*
C24	0.8620 (3)	−0.1173 (2)	−0.1443 (2)	0.0532 (6)
H24	0.9185	−0.0804	−0.1734	0.064*
C25	0.7690 (2)	0.34949 (17)	−0.18724 (18)	0.0367 (5)
C26	0.7993 (3)	0.3826 (2)	−0.2774 (2)	0.0466 (6)
H26	0.8847	0.3840	−0.2777	0.056*
C27	0.7010 (3)	0.4132 (2)	−0.3663 (2)	0.0621 (8)
H27	0.7206	0.4345	−0.4271	0.075*
C28	0.5748 (3)	0.4127 (3)	−0.3663 (2)	0.0661 (8)
H28	0.5097	0.4340	−0.4264	0.079*
C29	0.5450 (3)	0.3804 (2)	−0.2768 (2)	0.0599 (7)
H29	0.4597	0.3804	−0.2763	0.072*
C30	0.6417 (2)	0.3480 (2)	−0.1879 (2)	0.0454 (6)
H30	0.6210	0.3250	−0.1283	0.054*

	U11	U22	U33	U12	U13	U23
Cl1	0.1326 (8)	0.0500 (4)	0.1256 (7)	−0.0044 (4)	0.0769 (6)	0.0270 (5)
S1	0.0814 (5)	0.0344 (3)	0.0551 (4)	−0.0089 (3)	0.0419 (4)	−0.0015 (3)
N1	0.0592 (13)	0.0348 (10)	0.0453 (11)	−0.0037 (9)	0.0270 (10)	0.0030 (9)
N2	0.0562 (13)	0.0326 (10)	0.0416 (11)	−0.0012 (9)	0.0257 (10)	0.0072 (8)
N3	0.0549 (12)	0.0273 (9)	0.0405 (10)	0.0031 (8)	0.0231 (9)	0.0092 (8)
N4	0.0485 (12)	0.0268 (9)	0.0376 (10)	0.0031 (8)	0.0220 (9)	0.0095 (8)
N5	0.0684 (15)	0.0268 (9)	0.0482 (12)	0.0058 (9)	0.0333 (11)	0.0095 (9)
N6	0.0462 (13)	0.0320 (10)	0.0425 (11)	0.0015 (9)	0.0247 (10)	0.0097 (8)
O1	0.0586 (11)	0.0292 (8)	0.0553 (10)	−0.0024 (7)	0.0322 (8)	0.0093 (7)
C1	0.0506 (15)	0.0322 (11)	0.0431 (13)	−0.0009 (10)	0.0233 (11)	0.0042 (10)
C2	0.0441 (14)	0.0295 (11)	0.0390 (12)	−0.0009 (9)	0.0190 (10)	0.0060 (9)
C3	0.0446 (14)	0.0326 (11)	0.0362 (12)	0.0020 (10)	0.0175 (10)	0.0099 (9)
C4	0.0435 (14)	0.0272 (10)	0.0385 (12)	0.0043 (9)	0.0163 (10)	0.0100 (9)
C5	0.0364 (13)	0.0297 (11)	0.0419 (12)	0.0019 (9)	0.0160 (10)	0.0078 (9)
C6	0.081 (2)	0.0429 (14)	0.0478 (15)	−0.0009 (13)	0.0318 (14)	0.0046 (11)
C7	0.0543 (16)	0.0395 (12)	0.0403 (13)	0.0015 (11)	0.0266 (12)	0.0035 (10)
C8	0.0528 (17)	0.0561 (16)	0.0603 (16)	0.0026 (13)	0.0232 (13)	0.0114 (13)
C9	0.074 (2)	0.0498 (16)	0.085 (2)	0.0168 (15)	0.0418 (18)	0.0178 (15)
C10	0.087 (2)	0.0399 (14)	0.087 (2)	−0.0006 (16)	0.0523 (19)	0.0005 (14)
C11	0.061 (2)	0.0630 (19)	0.083 (2)	−0.0084 (16)	0.0222 (17)	−0.0132 (16)
C12	0.0561 (18)	0.0586 (17)	0.0715 (19)	0.0141 (14)	0.0196 (15)	0.0030 (14)
C13	0.0484 (15)	0.0421 (12)	0.0358 (12)	−0.0045 (11)	0.0161 (11)	0.0122 (10)
C14	0.0707 (19)	0.0505 (15)	0.0511 (15)	−0.0058 (13)	0.0332 (14)	0.0051 (12)
C15	0.076 (2)	0.077 (2)	0.0628 (18)	−0.0123 (16)	0.0422 (16)	0.0110 (15)
C16	0.074 (2)	0.0634 (18)	0.0602 (17)	−0.0176 (15)	0.0256 (15)	0.0226 (14)
C17	0.077 (2)	0.0452 (14)	0.0671 (18)	−0.0042 (14)	0.0309 (16)	0.0218 (13)
C18	0.0669 (18)	0.0450 (14)	0.0590 (16)	0.0046 (12)	0.0314 (14)	0.0204 (12)
C19	0.0525 (15)	0.0284 (11)	0.0404 (13)	0.0054 (10)	0.0145 (11)	0.0079 (10)
C20	0.0653 (17)	0.0320 (12)	0.0514 (14)	0.0056 (11)	0.0260 (13)	0.0089 (11)
C21	0.0706 (19)	0.0365 (13)	0.0586 (16)	−0.0001 (12)	0.0230 (14)	0.0150 (12)
C22	0.086 (2)	0.0288 (12)	0.0727 (19)	0.0135 (13)	0.0263 (17)	0.0151 (13)
C23	0.075 (2)	0.0366 (13)	0.0789 (19)	0.0184 (13)	0.0331 (16)	0.0098 (13)
C24	0.0639 (18)	0.0365 (13)	0.0624 (16)	0.0082 (12)	0.0292 (14)	0.0103 (12)
C25	0.0520 (15)	0.0214 (10)	0.0363 (12)	0.0018 (9)	0.0186 (11)	0.0046 (9)
C26	0.0625 (17)	0.0385 (12)	0.0442 (14)	0.0022 (11)	0.0292 (13)	0.0083 (11)
C27	0.088 (2)	0.0571 (16)	0.0436 (15)	0.0016 (15)	0.0250 (15)	0.0192 (13)
C28	0.075 (2)	0.0660 (18)	0.0525 (17)	0.0097 (16)	0.0115 (15)	0.0254 (14)
C29	0.0521 (17)	0.0617 (17)	0.0612 (17)	0.0069 (13)	0.0148 (14)	0.0173 (14)
C30	0.0495 (16)	0.0426 (13)	0.0473 (14)	0.0013 (11)	0.0214 (12)	0.0140 (11)

Cl1—C21	1.746 (3)	C12—H12	0.9300
S1—C1	1.748 (2)	C13—C14	1.367 (3)
S1—C6	1.816 (2)	C13—C18	1.383 (3)
N1—C1	1.318 (3)	C14—C15	1.386 (3)
N1—N2	1.397 (2)	C14—H14	0.9300
N2—C3	1.357 (3)	C15—C16	1.373 (4)
N2—C13	1.430 (3)	C15—H15	0.9300
N3—C4	1.304 (3)	C16—C17	1.369 (4)
N3—C3	1.357 (3)	C16—H16	0.9300
N4—C4	1.389 (2)	C17—C18	1.387 (3)
N4—N6	1.409 (2)	C17—H17	0.9300
N4—C5	1.420 (3)	C18—H18	0.9300
N5—C4	1.351 (3)	C19—C20	1.376 (3)
N5—C19	1.415 (3)	C19—C24	1.392 (3)
N5—H5	0.79 (2)	C20—C21	1.388 (3)
N6—C25	1.426 (3)	C20—H20	0.9300
N6—H6	0.81 (2)	C21—C22	1.369 (4)
O1—C5	1.223 (2)	C22—C23	1.375 (4)
C1—C2	1.421 (3)	C22—H22	0.9300
C2—C3	1.388 (3)	C23—C24	1.384 (3)
C2—C5	1.420 (3)	C23—H23	0.9300
C6—C7	1.508 (3)	C24—H24	0.9300
C6—H6A	0.9700	C25—C30	1.381 (3)
C6—H6B	0.9700	C25—C26	1.393 (3)
C7—C12	1.369 (4)	C26—C27	1.382 (4)
C7—C8	1.377 (3)	C26—H26	0.9300
C8—C9	1.375 (4)	C27—C28	1.372 (4)
C8—H8	0.9300	C27—H27	0.9300
C9—C10	1.357 (4)	C28—C29	1.379 (4)
C9—H9	0.9300	C28—H28	0.9300
C10—C11	1.351 (4)	C29—C30	1.382 (3)
C10—H10	0.9300	C29—H29	0.9300
C11—C12	1.396 (4)	C30—H30	0.9300
C11—H11	0.9300
C1—S1—C6	101.17 (11)	C14—C13—C18	120.3 (2)
C1—N1—N2	105.43 (17)	C14—C13—N2	119.3 (2)
C3—N2—N1	110.80 (16)	C18—C13—N2	120.4 (2)
C3—N2—C13	129.75 (18)	C13—C14—C15	119.5 (2)
N1—N2—C13	118.85 (17)	C13—C14—H14	120.2
C4—N3—C3	113.84 (17)	C15—C14—H14	120.2
C4—N4—N6	117.28 (16)	C16—C15—C14	120.9 (3)
C4—N4—C5	123.97 (17)	C16—C15—H15	119.6
N6—N4—C5	118.71 (15)	C14—C15—H15	119.6
C4—N5—C19	128.2 (2)	C17—C16—C15	119.1 (2)
C4—N5—H5	115.2 (17)	C17—C16—H16	120.4
C19—N5—H5	115.4 (17)	C15—C16—H16	120.4
N4—N6—C25	114.04 (18)	C16—C17—C18	120.8 (3)
N4—N6—H6	109.4 (15)	C16—C17—H17	119.6
C25—N6—H6	114.9 (15)	C18—C17—H17	119.6
N1—C1—C2	111.45 (18)	C13—C18—C17	119.3 (2)
N1—C1—S1	123.62 (16)	C13—C18—H18	120.4
C2—C1—S1	124.93 (16)	C17—C18—H18	120.4
C3—C2—C5	119.40 (19)	C20—C19—C24	120.6 (2)
C3—C2—C1	105.10 (18)	C20—C19—N5	123.2 (2)
C5—C2—C1	135.25 (19)	C24—C19—N5	116.2 (2)
N3—C3—N2	125.70 (18)	C19—C20—C21	118.1 (2)
N3—C3—C2	127.08 (19)	C19—C20—H20	120.9
N2—C3—C2	107.21 (18)	C21—C20—H20	120.9
N3—C4—N5	121.72 (19)	C22—C21—C20	122.6 (2)
N3—C4—N4	123.69 (19)	C22—C21—Cl1	119.16 (19)
N5—C4—N4	114.59 (19)	C20—C21—Cl1	118.2 (2)
O1—C5—C2	128.6 (2)	C21—C22—C23	118.3 (2)
O1—C5—N4	119.93 (19)	C21—C22—H22	120.9
C2—C5—N4	111.51 (17)	C23—C22—H22	120.9
C7—C6—S1	108.09 (16)	C22—C23—C24	121.1 (2)
C7—C6—H6A	110.1	C22—C23—H23	119.4
S1—C6—H6A	110.1	C24—C23—H23	119.4
C7—C6—H6B	110.1	C23—C24—C19	119.2 (2)
S1—C6—H6B	110.1	C23—C24—H24	120.4
H6A—C6—H6B	108.4	C19—C24—H24	120.4
C12—C7—C8	118.1 (2)	C30—C25—C26	119.7 (2)
C12—C7—C6	121.6 (2)	C30—C25—N6	122.8 (2)
C8—C7—C6	120.3 (2)	C26—C25—N6	117.5 (2)
C9—C8—C7	121.3 (3)	C27—C26—C25	119.2 (2)
C9—C8—H8	119.3	C27—C26—H26	120.4
C7—C8—H8	119.3	C25—C26—H26	120.4
C10—C9—C8	119.9 (3)	C28—C27—C26	121.0 (2)
C10—C9—H9	120.1	C28—C27—H27	119.5
C8—C9—H9	120.1	C26—C27—H27	119.5
C11—C10—C9	120.1 (3)	C27—C28—C29	119.8 (3)
C11—C10—H10	120.0	C27—C28—H28	120.1
C9—C10—H10	120.0	C29—C28—H28	120.1
C10—C11—C12	120.3 (3)	C28—C29—C30	120.0 (3)
C10—C11—H11	119.9	C28—C29—H29	120.0
C12—C11—H11	119.9	C30—C29—H29	120.0
C7—C12—C11	120.3 (3)	C25—C30—C29	120.3 (2)
C7—C12—H12	119.9	C25—C30—H30	119.8
C11—C12—H12	119.9	C29—C30—H30	119.8
C1—N1—N2—C3	0.7 (3)	C6—C7—C8—C9	179.4 (2)
C1—N1—N2—C13	−171.3 (2)	C7—C8—C9—C10	0.7 (4)
C4—N4—N6—C25	100.4 (2)	C8—C9—C10—C11	1.1 (4)
C5—N4—N6—C25	−77.3 (2)	C9—C10—C11—C12	−1.3 (5)
N2—N1—C1—C2	0.0 (3)	C8—C7—C12—C11	2.0 (4)
N2—N1—C1—S1	−179.17 (17)	C6—C7—C12—C11	−179.6 (2)
C6—S1—C1—N1	13.9 (2)	C10—C11—C12—C7	−0.3 (5)
C6—S1—C1—C2	−165.1 (2)	C3—N2—C13—C14	−149.5 (2)
N1—C1—C2—C3	−0.6 (3)	N1—N2—C13—C14	20.7 (3)
S1—C1—C2—C3	178.52 (17)	C3—N2—C13—C18	29.3 (4)
N1—C1—C2—C5	173.3 (2)	N1—N2—C13—C18	−160.5 (2)
S1—C1—C2—C5	−7.5 (4)	C18—C13—C14—C15	1.0 (4)
C4—N3—C3—N2	178.3 (2)	N2—C13—C14—C15	179.8 (2)
C4—N3—C3—C2	−3.2 (3)	C13—C14—C15—C16	−0.4 (4)
N1—N2—C3—N3	177.6 (2)	C14—C15—C16—C17	−0.9 (4)
C13—N2—C3—N3	−11.5 (4)	C15—C16—C17—C18	1.6 (4)
N1—N2—C3—C2	−1.1 (3)	C14—C13—C18—C17	−0.3 (4)
C13—N2—C3—C2	169.7 (2)	N2—C13—C18—C17	−179.1 (2)
C5—C2—C3—N3	7.2 (4)	C16—C17—C18—C13	−1.0 (4)
C1—C2—C3—N3	−177.7 (2)	C4—N5—C19—C20	30.2 (4)
C5—C2—C3—N2	−174.1 (2)	C4—N5—C19—C24	−152.2 (2)
C1—C2—C3—N2	1.0 (3)	C24—C19—C20—C21	2.0 (4)
C3—N3—C4—N5	176.6 (2)	N5—C19—C20—C21	179.5 (2)
C3—N3—C4—N4	−3.8 (3)	C19—C20—C21—C22	−1.5 (4)
C19—N5—C4—N3	−9.2 (4)	C19—C20—C21—Cl1	−179.75 (19)
C19—N5—C4—N4	171.1 (2)	C20—C21—C22—C23	−0.4 (4)
N6—N4—C4—N3	−170.6 (2)	Cl1—C21—C22—C23	177.8 (2)
C5—N4—C4—N3	6.9 (3)	C21—C22—C23—C24	1.8 (4)
N6—N4—C4—N5	9.1 (3)	C22—C23—C24—C19	−1.3 (4)
C5—N4—C4—N5	−173.4 (2)	C20—C19—C24—C23	−0.7 (4)
C3—C2—C5—O1	175.9 (2)	N5—C19—C24—C23	−178.3 (2)
C1—C2—C5—O1	2.6 (5)	N4—N6—C25—C30	−15.6 (3)
C3—C2—C5—N4	−3.7 (3)	N4—N6—C25—C26	167.26 (17)
C1—C2—C5—N4	−177.0 (2)	C30—C25—C26—C27	−0.1 (3)
C4—N4—C5—O1	177.8 (2)	N6—C25—C26—C27	177.1 (2)
N6—N4—C5—O1	−4.7 (3)	C25—C26—C27—C28	0.6 (4)
C4—N4—C5—C2	−2.6 (3)	C26—C27—C28—C29	−0.4 (4)
N6—N4—C5—C2	174.89 (19)	C27—C28—C29—C30	−0.4 (4)
C1—S1—C6—C7	−175.34 (19)	C26—C25—C30—C29	−0.7 (3)
S1—C6—C7—C12	−96.8 (3)	N6—C25—C30—C29	−177.8 (2)
S1—C6—C7—C8	81.5 (3)	C28—C29—C30—C25	0.9 (4)
C12—C7—C8—C9	−2.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5···N6	0.79 (2)	2.19 (2)	2.605 (3)	114 (2)
N6—H6···O1i	0.81 (2)	2.12 (2)	2.904 (3)	162 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5⋯N6	0.79 (2)	2.19 (2)	2.605 (3)	114 (2)
N6—H6⋯O1i	0.81 (2)	2.12 (2)	2.904 (3)	162 (2)

Symmetry code: (i) .