6-{5-Amino-3-tert-butyl-4-[(E)-(3-methyl-1,2,4-thiadiazol-5-yl)diazen-yl]-1H-pyrazol-1-yl}-1,3,5-triazine-2,4(1H,3H)-dione-1-methyl-pyrrolidin-2-one-water (1/1/1).

In the title compound, C(13)H(16)N(10)O(2)S·C(5)H(9)NO·H(2)O, the entire 1-methylpyrrolidin-2-one (NMP) mol-ecule is disordered over two sites with occupancies of 0.488 (5) and 0.512 (5). The six-membered triazine ring and the two five-membered pyrazole and thiadia-zole rings, together with the diazene (-N=N-) linkage are almost coplanar (r.m.s. deviation for the non-H atoms = 0.0256 Å) with methyl groups from the tert-butyl substituent on the pyrazole ring located above and below the plane. Three intra-molecular N-H⋯N hydrogen bonds contribute to the planarity of the system. The O atom of the NMP mol-ecule is hydrogen bonded to an O-H group of water. In turn, the water mol-ecule is hydrogen bonded to the mono-azo skeleton through inter-molecular N-H⋯O and O-H⋯N hydrogen bonds. At both ends of the long mol-ecular axis of the main mol-ecule there are inter-molecular N-H⋯N hydrogen bonds, arranged in a head-to-tail fashion, between the N-H group of the triazine ring of one mol-ecule and the N atom of the thia-diazole ring of a neighboring mol-ecule. These form a polymeric chain along [110] or [10]. The main mol-ecules are stacked alternately along the b axis, which effectively cancels their dipole moments. In addition, pairs of alternate molecules are dimerized via inter-molecular hydrogen bonds involving the solvent mol-ecules.

Related literature

For details of azo pigments, see: Herbst & Hunger (2004 ▶). For the structure of the Na(I) complex of the related bis-azo compound, see: Shibata & Mizuguchi (2010 ▶). For the synthesis of the title compound, see: Nagata & Tateishi (2009 ▶).

Experimental

Crystal data

C13H16N10O2S·C5H9NO·H2O

M = 493.54

Monoclinic,

a = 27.8283 (5) Å

b = 7.0269 (1) Å

c = 23.4417 (4) Å

β = 91.3430 (7)°

V = 4582.69 (13) Å3

Z = 8

Cu Kα radiation

μ = 1.70 mm−1

T = 93 K

0.50 × 0.10 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer

Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.529, T max = 0.844

3977 measured reflections

3977 independent reflections

3083 reflections with F 2 > 2σ(F 2)

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.150

S = 1.13

3977 reflections

347 parameters

84 restraints

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.35 e Å−3

Data collection: PROCESS-AUTO (Rigaku, 1998 ▶); cell refinement: PROCESS-AUTO; data reduction: CrystalStructure (Rigaku/MSC & Rigaku, 2006 ▶); program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▶); software used to prepare material for publication: CrystalStructure (Rigaku/MSC & Rigaku, 2006 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810010871/sj2752sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010871/sj2752Isup2.hkl

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

C13H16N10O2S·C5H9NO·H2O	F(000) = 2080.00
Mr = 493.54	Dx = 1.431 Mg m−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54187 Å
Hall symbol: -C 2yc	Cell parameters from 23604 reflections
a = 27.8283 (5) Å	θ = 3.2–68.2°
b = 7.0269 (1) Å	µ = 1.70 mm−1
c = 23.4417 (4) Å	T = 93 K
β = 91.3430 (7)°	Needle, yellow
V = 4582.69 (13) Å3	0.50 × 0.10 × 0.10 mm
Z = 8

Rigaku R-AXIS RAPID diffractometer	3083 reflections with F2 > 2σ(F2)
Detector resolution: 10.00 pixels mm-1	Rint = 0.0000
ω scans	θmax = 68.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = 0→33
Tmin = 0.529, Tmax = 0.844	k = 0→7
3977 measured reflections	l = −28→28
3977 independent reflections

Refinement on F2	84 restraints
R[F2 > 2σ(F2)] = 0.049	H-atom parameters constrained
wR(F2) = 0.150	w = 1/[σ2(Fo2) + (0.0944P)2] where P = (Fo2 + 2Fc2)/3
S = 1.13	(Δ/σ)max < 0.001
3977 reflections	Δρmax = 0.39 e Å−3
347 parameters	Δρmin = −0.35 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	Occ. (<1)
S1	0.07691 (2)	0.68241 (9)	0.52778 (2)	0.02961 (19)
O1	0.40973 (6)	0.2937 (3)	0.41323 (7)	0.0373 (5)
N1	0.43390 (7)	0.3073 (3)	0.50624 (9)	0.0308 (5)
H1N	0.4631	0.2738	0.4965	0.037*
N2	0.37906 (7)	0.3899 (3)	0.57444 (8)	0.0299 (5)
H2	0.3705	0.4104	0.6098	0.036*
N3	0.35360 (7)	0.3813 (3)	0.47740 (8)	0.0282 (5)
N4	0.30101 (7)	0.4672 (3)	0.54684 (8)	0.0289 (5)
N5	0.29244 (7)	0.5038 (3)	0.60491 (8)	0.0300 (5)
N6	0.17773 (7)	0.5903 (3)	0.53920 (8)	0.0283 (5)
N7	0.16607 (7)	0.5794 (3)	0.48524 (8)	0.0299 (5)
N8	0.09905 (7)	0.6256 (3)	0.42446 (9)	0.0332 (5)
N9	0.03348 (7)	0.7075 (3)	0.47827 (9)	0.0327 (5)
N10	0.25877 (7)	0.4604 (3)	0.45724 (8)	0.0292 (5)
H10N	0.2847	0.4226	0.4397	0.035*
H10M	0.2317	0.4780	0.4377	0.035*
C1	0.39937 (8)	0.3258 (4)	0.46226 (11)	0.0288 (5)
C2	0.42627 (9)	0.3368 (4)	0.56318 (11)	0.0308 (6)
C3	0.34649 (8)	0.4099 (4)	0.53120 (10)	0.0276 (5)
C4	0.24716 (8)	0.5503 (4)	0.60692 (10)	0.0281 (5)
C5	0.22433 (8)	0.5469 (4)	0.55086 (10)	0.0285 (6)
C6	0.26045 (9)	0.4907 (4)	0.51269 (10)	0.0286 (5)
C7	0.11800 (9)	0.6252 (4)	0.47621 (10)	0.0292 (5)
C8	0.05135 (9)	0.6725 (4)	0.42785 (11)	0.0331 (6)
C9	0.02131 (11)	0.6866 (6)	0.37484 (13)	0.0563 (9)
H9A	−0.0123	0.7067	0.3847	0.084*
H9B	0.0241	0.5686	0.3529	0.084*
H9C	0.0324	0.7939	0.3519	0.084*
C10	0.22345 (9)	0.5893 (4)	0.66330 (11)	0.0321 (6)
C11	0.26138 (9)	0.5910 (4)	0.71164 (11)	0.0382 (6)
H11A	0.2841	0.6953	0.7055	0.057*
H11B	0.2787	0.4696	0.7121	0.057*
H11C	0.2456	0.6092	0.7482	0.057*
C12	0.19714 (9)	0.7813 (4)	0.66161 (11)	0.0384 (7)
H12A	0.1812	0.8021	0.6980	0.058*
H12B	0.1730	0.7807	0.6305	0.058*
H12C	0.2203	0.8836	0.6553	0.058*
C13	0.18754 (9)	0.4262 (5)	0.67302 (11)	0.0412 (7)
H13A	0.1714	0.4464	0.7092	0.062*
H13B	0.2048	0.3047	0.6744	0.062*
H13C	0.1636	0.4239	0.6417	0.062*
O2	0.45672 (6)	0.3194 (3)	0.60030 (8)	0.0383 (5)
O4	0.18713 (7)	0.4753 (3)	0.35961 (8)	0.0463 (5)
H4A	0.1719	0.3757	0.3430	0.056*
H4B	0.1611	0.5393	0.3707	0.056*
O3A	0.13169 (17)	0.1331 (6)	0.30823 (16)	0.0335 (13)	0.488 (5)
C14A	0.10177 (11)	0.1786 (4)	0.27041 (11)	0.0290 (15)	0.488 (5)
C15A	0.07874 (15)	0.3737 (4)	0.25815 (16)	0.0457 (16)	0.488 (5)
H15A	0.1031	0.4764	0.2596	0.055*	0.488 (5)
H15B	0.0533	0.4025	0.2857	0.055*	0.488 (5)
C16A	0.05744 (16)	0.3497 (5)	0.19745 (16)	0.0485 (17)	0.488 (5)
H16A	0.0273	0.4232	0.1926	0.058*	0.488 (5)
H16B	0.0805	0.3930	0.1687	0.058*	0.488 (5)
C17A	0.04784 (13)	0.1366 (5)	0.19163 (14)	0.0356 (16)	0.488 (5)
H17A	0.0145	0.1050	0.2021	0.043*	0.488 (5)
H17B	0.0534	0.0923	0.1522	0.043*	0.488 (5)
N11A	0.08266 (10)	0.0533 (4)	0.23192 (11)	0.0322 (12)	0.488 (5)
C18A	0.09354 (17)	−0.1506 (4)	0.23177 (18)	0.0488 (17)	0.488 (5)
H18A	0.1050	−0.1876	0.1941	0.073*	0.488 (5)
H18B	0.0644	−0.2227	0.2403	0.073*	0.488 (5)
H18C	0.1185	−0.1780	0.2608	0.073*	0.488 (5)
O3B	0.12735 (16)	0.2045 (5)	0.31146 (16)	0.0311 (12)	0.512 (5)
C14B	0.10602 (10)	0.1110 (4)	0.27360 (11)	0.0333 (16)	0.512 (5)
C15B	0.10728 (13)	−0.1044 (4)	0.26215 (16)	0.0413 (14)	0.512 (5)
H15C	0.1044	−0.1776	0.2980	0.050*	0.512 (5)
H15D	0.1373	−0.1416	0.2433	0.050*	0.512 (5)
C16B	0.06328 (14)	−0.1355 (4)	0.22232 (17)	0.0423 (14)	0.512 (5)
H16C	0.0695	−0.2378	0.1944	0.051*	0.512 (5)
H16D	0.0347	−0.1699	0.2444	0.051*	0.512 (5)
C17B	0.05587 (13)	0.0551 (5)	0.19218 (13)	0.0394 (16)	0.512 (5)
H17C	0.0727	0.0584	0.1554	0.047*	0.512 (5)
H17D	0.0213	0.0814	0.1851	0.047*	0.512 (5)
N11B	0.07691 (9)	0.1908 (3)	0.23277 (10)	0.0354 (12)	0.512 (5)
C18B	0.06870 (15)	0.3959 (4)	0.22719 (17)	0.0419 (15)	0.512 (5)
H18D	0.0343	0.4226	0.2301	0.063*	0.512 (5)
H18E	0.0799	0.4393	0.1901	0.063*	0.512 (5)
H18F	0.0864	0.4630	0.2577	0.063*	0.512 (5)

	U11	U22	U33	U12	U13	U23
S1	0.0231 (3)	0.0402 (4)	0.0255 (3)	0.0041 (2)	0.0000 (2)	−0.0017 (3)
O1	0.0262 (9)	0.0595 (13)	0.0264 (9)	0.0060 (8)	0.0017 (7)	−0.0019 (8)
N1	0.0183 (10)	0.0433 (13)	0.0307 (11)	0.0024 (9)	0.0007 (8)	−0.0018 (9)
N2	0.0233 (10)	0.0437 (13)	0.0227 (10)	0.0029 (9)	−0.0004 (8)	−0.0026 (9)
N3	0.0214 (10)	0.0370 (12)	0.0262 (11)	0.0010 (8)	0.0007 (8)	0.0011 (9)
N4	0.0228 (10)	0.0396 (13)	0.0241 (11)	0.0026 (9)	0.0001 (8)	−0.0009 (9)
N5	0.0244 (11)	0.0404 (13)	0.0253 (11)	0.0031 (9)	0.0021 (8)	−0.0026 (9)
N6	0.0259 (10)	0.0317 (12)	0.0271 (11)	0.0010 (8)	−0.0007 (8)	0.0004 (9)
N7	0.0232 (10)	0.0397 (13)	0.0265 (11)	0.0024 (9)	−0.0023 (8)	0.0000 (9)
N8	0.0266 (11)	0.0457 (14)	0.0272 (11)	0.0074 (9)	−0.0014 (9)	−0.0016 (10)
N9	0.0250 (11)	0.0437 (14)	0.0291 (11)	0.0057 (9)	−0.0020 (8)	−0.0013 (9)
N10	0.0243 (10)	0.0402 (13)	0.0231 (10)	0.0054 (9)	−0.0001 (8)	−0.0008 (9)
C1	0.0230 (12)	0.0336 (15)	0.0298 (13)	0.0001 (10)	0.0003 (10)	0.0012 (10)
C2	0.0238 (12)	0.0367 (15)	0.0318 (13)	0.0011 (10)	−0.0006 (10)	−0.0001 (11)
C3	0.0212 (12)	0.0323 (14)	0.0294 (13)	0.0005 (9)	−0.0003 (9)	0.0002 (10)
C4	0.0239 (12)	0.0338 (14)	0.0266 (13)	0.0028 (10)	0.0002 (9)	0.0001 (10)
C5	0.0260 (12)	0.0334 (14)	0.0260 (12)	0.0043 (10)	−0.0009 (10)	−0.0002 (10)
C6	0.0251 (12)	0.0320 (14)	0.0287 (13)	0.0008 (10)	−0.0019 (9)	0.0015 (10)
C7	0.0270 (13)	0.0337 (14)	0.0269 (12)	0.0050 (10)	0.0012 (10)	−0.0010 (10)
C8	0.0286 (13)	0.0426 (16)	0.0279 (13)	0.0079 (11)	−0.0029 (10)	−0.0014 (11)
C9	0.0387 (16)	0.097 (3)	0.0328 (16)	0.0236 (17)	−0.0070 (13)	−0.0088 (16)
C10	0.0233 (12)	0.0473 (17)	0.0258 (13)	0.0029 (11)	0.0035 (10)	−0.0005 (11)
C11	0.0324 (14)	0.0559 (18)	0.0264 (13)	0.0058 (12)	0.0007 (10)	−0.0014 (12)
C12	0.0321 (14)	0.0549 (19)	0.0282 (14)	0.0083 (12)	0.0016 (11)	−0.0045 (12)
C13	0.0325 (15)	0.059 (2)	0.0319 (15)	−0.0042 (13)	0.0063 (11)	0.0026 (13)
O2	0.0251 (9)	0.0573 (13)	0.0323 (10)	0.0053 (8)	−0.0068 (7)	−0.0020 (8)
O4	0.0331 (10)	0.0676 (15)	0.0383 (11)	0.0036 (9)	0.0018 (8)	−0.0084 (10)
O3A	0.030 (2)	0.051 (3)	0.020 (2)	0.018 (2)	−0.0027 (17)	−0.018 (2)
C14A	0.016 (2)	0.051 (3)	0.021 (3)	0.004 (2)	−0.001 (2)	0.001 (2)
C15A	0.040 (3)	0.048 (4)	0.049 (4)	0.008 (3)	0.001 (3)	−0.001 (3)
C16A	0.053 (4)	0.052 (4)	0.040 (3)	0.012 (3)	−0.007 (3)	0.005 (3)
C17A	0.031 (3)	0.044 (4)	0.032 (3)	0.007 (3)	−0.004 (2)	−0.004 (3)
N11A	0.031 (2)	0.041 (3)	0.024 (2)	0.002 (2)	−0.0028 (18)	−0.001 (2)
C18A	0.060 (4)	0.044 (4)	0.042 (4)	0.008 (3)	0.001 (3)	−0.004 (3)
O3B	0.032 (2)	0.030 (3)	0.031 (2)	0.0077 (19)	−0.0010 (18)	−0.0098 (18)
C14B	0.032 (3)	0.039 (3)	0.030 (3)	−0.001 (2)	0.012 (3)	−0.002 (2)
C15B	0.040 (3)	0.041 (3)	0.043 (3)	−0.001 (2)	−0.004 (3)	0.000 (3)
C16B	0.043 (3)	0.043 (3)	0.040 (3)	−0.006 (3)	−0.001 (3)	−0.003 (2)
C17B	0.032 (3)	0.051 (4)	0.035 (3)	0.004 (3)	−0.003 (2)	−0.007 (3)
N11B	0.030 (2)	0.043 (3)	0.032 (2)	−0.0011 (19)	−0.0004 (19)	0.000 (2)
C18B	0.042 (3)	0.043 (3)	0.040 (4)	0.000 (3)	−0.001 (3)	0.002 (3)

S1—N9	1.665 (2)	C12—H12B	0.9800
S1—C7	1.731 (2)	C12—H12C	0.9800
O1—C1	1.213 (3)	C13—H13A	0.9800
N1—C2	1.372 (3)	C13—H13B	0.9800
N1—C1	1.399 (3)	C13—H13C	0.9800
N1—H1N	0.8800	O4—H4A	0.9018
N2—C3	1.351 (3)	O4—H4B	0.8962
N2—C2	1.397 (3)	O3A—C14A	1.2437
N2—H2	0.8800	C14A—N11A	1.3603
N3—C3	1.297 (3)	C14A—C15A	1.5375
N3—C1	1.386 (3)	C15A—C16A	1.5378
N4—C6	1.378 (3)	C15A—H15A	0.9900
N4—C3	1.385 (3)	C15A—H15B	0.9900
N4—N5	1.411 (3)	C16A—C17A	1.5263
N5—C4	1.304 (3)	C16A—H16A	0.9900
N6—N7	1.301 (3)	C16A—H16B	0.9900
N6—C5	1.354 (3)	C17A—N11A	1.4598
N7—C7	1.388 (3)	C17A—H17A	0.9900
N8—C7	1.311 (3)	C17A—H17B	0.9900
N8—C8	1.372 (3)	N11A—C18A	1.4644
N9—C8	1.316 (3)	C18A—H18A	0.9800
N10—C6	1.317 (3)	C18A—H18B	0.9800
N10—H10N	0.8800	C18A—H18C	0.9800
N10—H10M	0.8800	O3B—C14B	1.2436
C2—O2	1.207 (3)	C14B—N11B	1.3603
C4—C5	1.446 (3)	C14B—C15B	1.5375
C4—C10	1.516 (3)	C15B—C16B	1.5379
C5—C6	1.417 (3)	C15B—H15C	0.9900
C8—C9	1.485 (3)	C15B—H15D	0.9900
C9—H9A	0.9800	C16B—C17B	1.5263
C9—H9B	0.9800	C16B—H16C	0.9900
C9—H9C	0.9800	C16B—H16D	0.9900
C10—C11	1.530 (3)	C17B—N11B	1.4599
C10—C12	1.535 (4)	C17B—H17C	0.9900
C10—C13	1.541 (4)	C17B—H17D	0.9900
C11—H11A	0.9800	N11B—C18B	1.4644
C11—H11B	0.9800	C18B—H18D	0.9800
C11—H11C	0.9800	C18B—H18E	0.9800
C12—H12A	0.9800	C18B—H18F	0.9800
N9—S1—C7	91.05 (11)	C10—C12—H12C	109.5
C2—N1—C1	125.7 (2)	H12A—C12—H12C	109.5
C2—N1—H1N	117.1	H12B—C12—H12C	109.5
C1—N1—H1N	117.1	C10—C13—H13A	109.5
C3—N2—C2	120.2 (2)	C10—C13—H13B	109.5
C3—N2—H2	119.9	H13A—C13—H13B	109.5
C2—N2—H2	119.9	C10—C13—H13C	109.5
C3—N3—C1	117.1 (2)	H13A—C13—H13C	109.5
C6—N4—C3	128.4 (2)	H13B—C13—H13C	109.5
C6—N4—N5	112.57 (19)	H4A—O4—H4B	98.0
C3—N4—N5	118.97 (19)	O3A—C14A—N11A	123.4
C4—N5—N4	105.43 (19)	O3A—C14A—C15A	129.2
N7—N6—C5	113.5 (2)	N11A—C14A—C15A	107.4
N6—N7—C7	110.6 (2)	C14A—C15A—C16A	103.0
C7—N8—C8	108.4 (2)	C14A—C15A—H15A	111.2
C8—N9—S1	108.82 (17)	C16A—C15A—H15A	111.2
C6—N10—H10N	120.0	C14A—C15A—H15B	111.2
C6—N10—H10M	120.0	C16A—C15A—H15B	111.2
H10N—N10—H10M	120.0	H15A—C15A—H15B	109.1
O1—C1—N3	122.4 (2)	C17A—C16A—C15A	104.7
O1—C1—N1	120.5 (2)	C17A—C16A—H16A	110.8
N3—C1—N1	117.2 (2)	C15A—C16A—H16A	110.8
O2—C2—N1	124.3 (2)	C17A—C16A—H16B	110.8
O2—C2—N2	122.6 (2)	C15A—C16A—H16B	110.8
N1—C2—N2	113.1 (2)	H16A—C16A—H16B	108.9
N3—C3—N2	126.8 (2)	N11A—C17A—C16A	102.9
N3—C3—N4	117.6 (2)	N11A—C17A—H17A	111.2
N2—C3—N4	115.6 (2)	C16A—C17A—H17A	111.2
N5—C4—C5	111.6 (2)	N11A—C17A—H17B	111.2
N5—C4—C10	121.2 (2)	C16A—C17A—H17B	111.2
C5—C4—C10	127.2 (2)	H17A—C17A—H17B	109.1
N6—C5—C6	128.7 (2)	C14A—N11A—C17A	114.4
N6—C5—C4	125.3 (2)	C14A—N11A—C18A	123.9
C6—C5—C4	106.0 (2)	C17A—N11A—C18A	121.7
N10—C6—N4	124.3 (2)	O3B—C14B—N11B	123.4
N10—C6—C5	131.2 (2)	O3B—C14B—C15B	129.2
N4—C6—C5	104.5 (2)	N11B—C14B—C15B	107.4
N8—C7—N7	120.5 (2)	C14B—C15B—C16B	103.0
N8—C7—S1	112.82 (18)	C14B—C15B—H15C	111.2
N7—C7—S1	126.71 (18)	C16B—C15B—H15C	111.2
N9—C8—N8	118.9 (2)	C14B—C15B—H15D	111.2
N9—C8—C9	121.5 (2)	C16B—C15B—H15D	111.2
N8—C8—C9	119.6 (2)	H15C—C15B—H15D	109.1
C8—C9—H9A	109.5	C17B—C16B—C15B	104.7
C8—C9—H9B	109.5	C17B—C16B—H16C	110.8
H9A—C9—H9B	109.5	C15B—C16B—H16C	110.8
C8—C9—H9C	109.5	C17B—C16B—H16D	110.8
H9A—C9—H9C	109.5	C15B—C16B—H16D	110.8
H9B—C9—H9C	109.5	H16C—C16B—H16D	108.9
C4—C10—C11	109.9 (2)	N11B—C17B—C16B	102.9
C4—C10—C12	110.7 (2)	N11B—C17B—H17C	111.2
C11—C10—C12	109.4 (2)	C16B—C17B—H17C	111.2
C4—C10—C13	107.0 (2)	N11B—C17B—H17D	111.2
C11—C10—C13	109.6 (2)	C16B—C17B—H17D	111.2
C12—C10—C13	110.3 (2)	H17C—C17B—H17D	109.1
C10—C11—H11A	109.5	C14B—N11B—C17B	114.4
C10—C11—H11B	109.5	C14B—N11B—C18B	123.9
H11A—C11—H11B	109.5	C17B—N11B—C18B	121.7
C10—C11—H11C	109.5	N11B—C18B—H18D	109.5
H11A—C11—H11C	109.5	N11B—C18B—H18E	109.5
H11B—C11—H11C	109.5	H18D—C18B—H18E	109.5
C10—C12—H12A	109.5	N11B—C18B—H18F	109.5
C10—C12—H12B	109.5	H18D—C18B—H18F	109.5
H12A—C12—H12B	109.5	H18E—C18B—H18F	109.5
C6—N4—N5—C4	−0.2 (3)	C8—N8—C7—N7	179.1 (2)
C3—N4—N5—C4	−178.7 (2)	C8—N8—C7—S1	0.0 (3)
C5—N6—N7—C7	180.0 (2)	N6—N7—C7—N8	179.1 (2)
C7—S1—N9—C8	0.2 (2)	N6—N7—C7—S1	−2.0 (3)
C3—N3—C1—O1	179.3 (3)	N9—S1—C7—N8	−0.1 (2)
C3—N3—C1—N1	−0.6 (3)	N9—S1—C7—N7	−179.1 (2)
C2—N1—C1—O1	−178.9 (3)	S1—N9—C8—N8	−0.2 (3)
C2—N1—C1—N3	0.9 (4)	S1—N9—C8—C9	−179.0 (2)
C1—N1—C2—O2	179.8 (2)	C7—N8—C8—N9	0.1 (4)
C1—N1—C2—N2	−0.2 (4)	C7—N8—C8—C9	178.9 (3)
C3—N2—C2—O2	179.1 (2)	N5—C4—C10—C11	7.4 (4)
C3—N2—C2—N1	−0.9 (3)	C5—C4—C10—C11	−176.5 (3)
C1—N3—C3—N2	−0.5 (4)	N5—C4—C10—C12	128.4 (3)
C1—N3—C3—N4	179.4 (2)	C5—C4—C10—C12	−55.6 (3)
C2—N2—C3—N3	1.3 (4)	N5—C4—C10—C13	−111.4 (3)
C2—N2—C3—N4	−178.6 (2)	C5—C4—C10—C13	64.6 (3)
C6—N4—C3—N3	3.2 (4)	O3A—C14A—C15A—C16A	164.1
N5—N4—C3—N3	−178.5 (2)	N11A—C14A—C15A—C16A	−17.2
C6—N4—C3—N2	−176.8 (2)	C14A—C15A—C16A—C17A	26.5
N5—N4—C3—N2	1.4 (3)	C15A—C16A—C17A—N11A	−26.1
N4—N5—C4—C5	−0.2 (3)	O3A—C14A—N11A—C17A	179.4
N4—N5—C4—C10	176.4 (2)	C15A—C14A—N11A—C17A	0.6
N7—N6—C5—C6	−0.9 (4)	O3A—C14A—N11A—C18A	2.4
N7—N6—C5—C4	179.0 (2)	C15A—C14A—N11A—C18A	−176.4
N5—C4—C5—N6	−179.3 (2)	C16A—C17A—N11A—C14A	16.4
C10—C4—C5—N6	4.3 (4)	C16A—C17A—N11A—C18A	−166.5
N5—C4—C5—C6	0.5 (3)	O3B—C14B—C15B—C16B	164.0
C10—C4—C5—C6	−175.8 (2)	N11B—C14B—C15B—C16B	−17.2
C3—N4—C6—N10	0.1 (4)	C14B—C15B—C16B—C17B	26.5
N5—N4—C6—N10	−178.2 (2)	C15B—C16B—C17B—N11B	−26.1
C3—N4—C6—C5	178.9 (2)	O3B—C14B—N11B—C17B	179.4
N5—N4—C6—C5	0.5 (3)	C15B—C14B—N11B—C17B	0.6
N6—C5—C6—N10	−2.2 (5)	O3B—C14B—N11B—C18B	2.4
C4—C5—C6—N10	178.0 (3)	C15B—C14B—N11B—C18B	−176.4
N6—C5—C6—N4	179.2 (3)	C16B—C17B—N11B—C14B	16.4
C4—C5—C6—N4	−0.6 (3)	C16B—C17B—N11B—C18B	−166.5

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O3A	0.902	2.186	3.087 (4)	175.8
O4—H4A···O3B	0.902	1.868	2.752 (4)	166.3
O4—H4B···N7	0.896	2.700	3.104 (2)	108.5
O4—H4B···N8	0.896	2.245	3.100 (2)	159.4
N1—H1N···N9i	0.88	2.07	2.947 (2)	176
N2—H2···N5	0.88	2.27	2.654 (2)	106
N2—H2···O3Aii	0.88	1.95	2.778 (4)	157
N2—H2···O3Bii	0.88	2.01	2.766 (4)	143
N10—H10N···N3	0.88	2.11	2.727 (2)	126
N10—H10M···O4	0.88	2.19	3.002 (2)	154
N10—H10M···N7	0.88	2.28	2.804 (2)	119

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4A⋯O3A	0.90	2.19	3.087 (4)	176
O4—H4A⋯O3B	0.90	1.87	2.752 (4)	166
O4—H4B⋯N7	0.90	2.70	3.104 (2)	109
O4—H4B⋯N8	0.90	2.25	3.100 (2)	159
N1—H1N⋯N9i	0.88	2.07	2.947 (2)	176
N2—H2⋯N5	0.88	2.27	2.654 (2)	106
N2—H2⋯O3Aii	0.88	1.95	2.778 (4)	157
N2—H2⋯O3Bii	0.88	2.01	2.766 (4)	143
N10—H10N⋯N3	0.88	2.11	2.727 (2)	126
N10—H10M⋯O4	0.88	2.19	3.002 (2)	154
N10—H10M⋯N7	0.88	2.28	2.804 (2)	119

Symmetry codes: (i) ; (ii) .