4-{3-[(2-Isopropyl-5-methyl-phen-oxy)meth-yl]-7H-1,2,4-triazolo[3,4-b][1,3,4]thia-diazin-6-yl}-3-(p-tol-yl)sydnone.

In the title triazolothia-diazin compound, C(24)H(24)N(6)O(3)S (systematic name: 4-{3-[(2-isopropyl-5-methyl-phen-oxy)meth-yl]-7H-1,2,4-triazolo[3,4-b][1,3,4]thia-diazin-6-yl}-3-(4-methyl-phen-yl)-1,2,3-oxadiazol-3-ium-5-olate), an intra-molecular C-H⋯O hydrogen bond generates an S(6) ring motif. The two terminal methyl groups of the isopropyl unit are disordered over two sets of positions in a 0.715 (4):0.285 (4) ratio. The mean planes formed through the major and minor disordered isopropyl units are inclined at inter-planar angles of 73.1 (4) and 86.6 (8)°, respectively, with the attached phenyl ring. The 3,6-dihydro-1,3,4-thia-diazine ring adopts a twist-boat conformation. The inter-planar angle formed between 1,2,3-oxadiazole and 1,2,4-triazole rings is 18.80 (11)°. In the crystal, neighbouring mol-ecules are linked into sheets lying parallel to the bc plane by C-H⋯N hydrogen bonds. Weak inter-molecular π-π inter-actions [centroid-centroid distances = 3.2935 (11) and 3.5590 (12) Å] further stabilize the crystal structure.

Related literature

For general background to and applications of materials related to the title triazolothia­diazine compound, see: Kalluraya & Rahiman (1997 ▶); Kalluraya et al. (2003 ▶); Newton & Ramsden (1982 ▶); Wagner & Hill (1974 ▶). For graph-set descriptions of hydrogen-bond ring motifs, see: Bernstein et al. (1995 ▶). For ring conformations and ring puckering analysis, see: Cremer & Pople (1975 ▶). For related structures, see: Goh et al. (2010 ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C24H24N6O3S

M = 476.55

Monoclinic,

a = 16.7814 (3) Å

b = 7.2901 (1) Å

c = 20.2221 (3) Å

β = 106.991 (1)°

V = 2365.95 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.18 mm−1

T = 100 K

0.25 × 0.21 × 0.07 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.958, T max = 0.988

20258 measured reflections

6897 independent reflections

4836 reflections with I > 2σ(I)

R int = 0.053

Refinement

R[F 2 > 2σ(F 2)] = 0.057

wR(F 2) = 0.162

S = 1.04

6897 reflections

314 parameters

H-atom parameters constrained

Δρmax = 0.68 e Å−3

Δρmin = −0.60 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810030205/hb5569sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810030205/hb5569Isup2.hkl

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

C24H24N6O3S	F(000) = 1000
Mr = 476.55	Dx = 1.338 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3586 reflections
a = 16.7814 (3) Å	θ = 3.7–30.0°
b = 7.2901 (1) Å	µ = 0.18 mm−1
c = 20.2221 (3) Å	T = 100 K
β = 106.991 (1)°	Plate, yellow
V = 2365.95 (6) Å3	0.25 × 0.21 × 0.07 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	6897 independent reflections
Radiation source: fine-focus sealed tube	4836 reflections with I > 2σ(I)
graphite	Rint = 0.053
φ and ω scans	θmax = 30.2°, θmin = 3.5°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −23→23
Tmin = 0.958, Tmax = 0.988	k = −10→9
20258 measured reflections	l = −28→26

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0787P)2 + 0.8879P] where P = (Fo2 + 2Fc2)/3
6897 reflections	(Δ/σ)max = 0.002
314 parameters	Δρmax = 0.68 e Å−3
0 restraints	Δρmin = −0.60 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1)K.

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 > 2sigma(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	1.12872 (3)	0.84837 (7)	0.02404 (3)	0.01713 (12)
O1	0.76141 (9)	0.7367 (3)	−0.02658 (8)	0.0334 (4)
O2	1.15782 (9)	1.0448 (2)	0.31193 (7)	0.0200 (3)
O3	1.24221 (9)	0.9624 (2)	0.24693 (8)	0.0237 (3)
N1	0.90823 (10)	0.6471 (2)	−0.06230 (9)	0.0171 (3)
N2	0.98873 (10)	0.6914 (2)	−0.06497 (9)	0.0174 (3)
N3	0.97931 (9)	0.7563 (2)	0.03891 (8)	0.0135 (3)
N4	0.99250 (10)	0.8392 (2)	0.10282 (8)	0.0146 (3)
N5	1.07442 (10)	1.0591 (2)	0.30466 (9)	0.0185 (3)
N6	1.03703 (10)	1.0015 (2)	0.24167 (8)	0.0150 (3)
C1	0.67088 (12)	0.6673 (3)	0.04511 (11)	0.0240 (4)
H1A	0.7144	0.6128	0.0788	0.029*
C2	0.59151 (13)	0.6753 (3)	0.05414 (11)	0.0232 (4)
C3	0.52834 (13)	0.7576 (3)	0.00321 (12)	0.0285 (5)
H3A	0.4750	0.7640	0.0081	0.034*
C4	0.54356 (13)	0.8308 (4)	−0.05515 (13)	0.0298 (5)
H4A	0.4999	0.8863	−0.0883	0.036*
C5	0.62153 (12)	0.8244 (3)	−0.06609 (11)	0.0242 (5)
C6	0.68510 (12)	0.7400 (3)	−0.01377 (10)	0.0181 (3)
C7	0.83038 (11)	0.6680 (3)	0.02616 (10)	0.0178 (4)
H7A	0.8219	0.5400	0.0354	0.021*
H7B	0.8383	0.7374	0.0685	0.021*
C8	0.90403 (11)	0.6888 (3)	−0.00054 (10)	0.0148 (4)
C9	1.02919 (11)	0.7570 (3)	−0.00414 (10)	0.0149 (4)
C10	1.14197 (11)	0.7915 (3)	0.11406 (10)	0.0164 (4)
H10A	1.1460	0.6594	0.1199	0.020*
H10B	1.1934	0.8451	0.1426	0.020*
C11	1.06984 (12)	0.8615 (3)	0.13761 (10)	0.0181 (3)
C12	1.09001 (11)	0.9487 (3)	0.20486 (10)	0.0150 (4)
C13	1.17215 (12)	0.9794 (3)	0.25034 (10)	0.0178 (4)
C14	0.94665 (11)	1.0107 (3)	0.22300 (10)	0.0148 (4)
C15	0.90726 (12)	0.9404 (3)	0.26880 (11)	0.0181 (4)
H15A	0.9378	0.8843	0.3097	0.022*
C16	0.82111 (13)	0.9555 (3)	0.25236 (11)	0.0212 (4)
H16A	0.7937	0.9074	0.2824	0.025*
C17	0.77504 (12)	1.0416 (3)	0.19151 (12)	0.0220 (4)
C18	0.81788 (13)	1.1146 (3)	0.14753 (11)	0.0213 (4)
H18A	0.7880	1.1733	0.1071	0.026*
C19	0.90384 (12)	1.1014 (3)	0.16288 (10)	0.0173 (4)
H19A	0.9318	1.1518	0.1337	0.021*
C20	0.57629 (14)	0.5967 (4)	0.11855 (13)	0.0304 (5)
H20A	0.5324	0.5076	0.1057	0.046*
H20B	0.5606	0.6935	0.1444	0.046*
H20C	0.6263	0.5392	0.1464	0.046*
C21	0.63844 (15)	0.8953 (4)	−0.13113 (13)	0.0365 (6)
H21A	0.6957	0.9417	−0.1180	0.044*	0.715 (4)
H21B	0.6927	0.8569	−0.1322	0.044*	0.285 (4)
C22	0.5837 (4)	1.0436 (9)	−0.1679 (3)	0.0728 (19)	0.715 (4)
H22A	0.5845	1.1429	−0.1365	0.109*	0.715 (4)
H22B	0.5278	0.9981	−0.1858	0.109*	0.715 (4)
H22C	0.6030	1.0865	−0.2054	0.109*	0.715 (4)
C23	0.6338 (3)	0.7265 (7)	−0.1815 (2)	0.0531 (11)	0.715 (4)
H23A	0.6492	0.7659	−0.2214	0.080*	0.715 (4)
H23B	0.5780	0.6789	−0.1958	0.080*	0.715 (4)
H23C	0.6715	0.6324	−0.1579	0.080*	0.715 (4)
C22X	0.6361 (9)	1.129 (2)	−0.1228 (8)	0.0728 (19)	0.285 (4)
H22D	0.6563	1.1860	−0.1576	0.109*	0.285 (4)
H22E	0.6709	1.1645	−0.0779	0.109*	0.285 (4)
H22F	0.5800	1.1684	−0.1283	0.109*	0.285 (4)
C23X	0.5773 (8)	0.8472 (19)	−0.1949 (5)	0.0531 (11)	0.285 (4)
H23D	0.5744	0.7161	−0.1995	0.080*	0.285 (4)
H23E	0.5928	0.8992	−0.2330	0.080*	0.285 (4)
H23F	0.5239	0.8940	−0.1948	0.080*	0.285 (4)
C24	0.68205 (13)	1.0618 (4)	0.17411 (14)	0.0315 (5)
H24A	0.6614	0.9817	0.2030	0.047*
H24B	0.6569	1.0302	0.1265	0.047*
H24C	0.6685	1.1864	0.1817	0.047*

	U11	U22	U33	U12	U13	U23
S1	0.0194 (2)	0.0186 (3)	0.0151 (2)	−0.00106 (17)	0.00760 (17)	0.00018 (19)
O1	0.0171 (7)	0.0642 (13)	0.0177 (8)	0.0052 (7)	0.0031 (6)	0.0140 (8)
O2	0.0215 (7)	0.0234 (8)	0.0134 (7)	−0.0021 (5)	0.0025 (5)	−0.0027 (6)
O3	0.0196 (7)	0.0290 (9)	0.0212 (8)	−0.0027 (6)	0.0037 (6)	−0.0027 (7)
N1	0.0191 (7)	0.0171 (9)	0.0135 (8)	−0.0002 (6)	0.0024 (6)	−0.0001 (7)
N2	0.0214 (7)	0.0175 (9)	0.0130 (8)	0.0004 (6)	0.0044 (6)	−0.0014 (6)
N3	0.0178 (7)	0.0124 (8)	0.0106 (7)	0.0003 (6)	0.0046 (6)	−0.0008 (6)
N4	0.0208 (7)	0.0140 (8)	0.0098 (7)	0.0000 (6)	0.0058 (6)	−0.0023 (6)
N5	0.0224 (8)	0.0182 (9)	0.0135 (8)	−0.0013 (6)	0.0031 (6)	−0.0026 (7)
N6	0.0200 (7)	0.0139 (8)	0.0108 (7)	−0.0002 (6)	0.0043 (6)	−0.0001 (6)
C1	0.0202 (9)	0.0315 (12)	0.0183 (10)	0.0003 (8)	0.0025 (8)	0.0001 (9)
C2	0.0239 (9)	0.0267 (12)	0.0195 (10)	−0.0044 (8)	0.0070 (8)	−0.0046 (9)
C3	0.0193 (9)	0.0385 (14)	0.0282 (12)	0.0028 (9)	0.0077 (8)	0.0007 (11)
C4	0.0204 (9)	0.0417 (15)	0.0261 (12)	0.0075 (9)	0.0053 (8)	0.0043 (11)
C5	0.0211 (9)	0.0322 (13)	0.0180 (10)	0.0014 (8)	0.0036 (8)	0.0028 (9)
C6	0.0178 (6)	0.0223 (8)	0.0137 (6)	−0.0003 (5)	0.0038 (5)	0.0003 (6)
C7	0.0171 (8)	0.0220 (11)	0.0126 (9)	0.0000 (7)	0.0018 (7)	0.0009 (8)
C8	0.0168 (8)	0.0131 (9)	0.0122 (9)	0.0004 (6)	0.0003 (7)	0.0017 (7)
C9	0.0188 (8)	0.0133 (9)	0.0132 (9)	0.0018 (7)	0.0057 (7)	0.0016 (7)
C10	0.0172 (8)	0.0193 (10)	0.0117 (9)	0.0014 (7)	0.0025 (7)	−0.0011 (7)
C11	0.0178 (6)	0.0223 (8)	0.0137 (6)	−0.0003 (5)	0.0038 (5)	0.0003 (6)
C12	0.0170 (8)	0.0161 (10)	0.0110 (8)	−0.0007 (7)	0.0028 (7)	0.0005 (7)
C13	0.0231 (9)	0.0168 (10)	0.0123 (9)	−0.0020 (7)	0.0033 (7)	−0.0007 (8)
C14	0.0170 (8)	0.0151 (9)	0.0112 (9)	0.0011 (7)	0.0026 (7)	−0.0024 (7)
C15	0.0254 (9)	0.0136 (10)	0.0164 (9)	−0.0001 (7)	0.0080 (8)	−0.0016 (8)
C16	0.0259 (10)	0.0196 (11)	0.0218 (10)	−0.0025 (8)	0.0125 (8)	−0.0034 (8)
C17	0.0209 (9)	0.0196 (11)	0.0247 (11)	0.0000 (7)	0.0053 (8)	−0.0068 (9)
C18	0.0253 (9)	0.0207 (11)	0.0176 (10)	0.0032 (8)	0.0056 (8)	−0.0033 (8)
C19	0.0237 (9)	0.0156 (10)	0.0138 (9)	0.0022 (7)	0.0074 (7)	−0.0013 (8)
C20	0.0279 (10)	0.0401 (14)	0.0257 (12)	−0.0037 (10)	0.0118 (9)	0.0017 (11)
C21	0.0254 (10)	0.0585 (18)	0.0252 (12)	0.0059 (11)	0.0068 (9)	0.0161 (12)
C22	0.075 (3)	0.095 (4)	0.062 (3)	0.051 (3)	0.041 (3)	0.057 (3)
C23	0.067 (3)	0.069 (3)	0.0283 (19)	−0.009 (2)	0.0221 (19)	−0.003 (2)
C22X	0.075 (3)	0.095 (4)	0.062 (3)	0.051 (3)	0.041 (3)	0.057 (3)
C23X	0.067 (3)	0.069 (3)	0.0283 (19)	−0.009 (2)	0.0221 (19)	−0.003 (2)
C24	0.0218 (10)	0.0323 (13)	0.0406 (14)	−0.0009 (9)	0.0094 (10)	−0.0063 (11)

S1—C9	1.7327 (19)	C14—C15	1.384 (3)
S1—C10	1.816 (2)	C14—C19	1.386 (3)
O1—C6	1.379 (2)	C15—C16	1.390 (3)
O1—C7	1.417 (2)	C15—H15A	0.9300
O2—N5	1.368 (2)	C16—C17	1.396 (3)
O2—C13	1.418 (2)	C16—H16A	0.9300
O3—C13	1.204 (2)	C17—C18	1.402 (3)
N1—C8	1.307 (2)	C17—C24	1.503 (3)
N1—N2	1.405 (2)	C18—C19	1.387 (3)
N2—C9	1.309 (2)	C18—H18A	0.9300
N3—C9	1.373 (2)	C19—H19A	0.9300
N3—C8	1.373 (2)	C20—H20A	0.9600
N3—N4	1.385 (2)	C20—H20B	0.9600
N4—C11	1.293 (2)	C20—H20C	0.9600
N5—N6	1.314 (2)	C21—C23X	1.438 (11)
N6—C12	1.371 (2)	C21—C22	1.472 (5)
N6—C14	1.453 (2)	C21—C23	1.585 (5)
C1—C6	1.387 (3)	C21—C22X	1.716 (16)
C1—C2	1.397 (3)	C21—H21A	0.9800
C1—H1A	0.9300	C21—H21B	0.9600
C2—C3	1.381 (3)	C22—H22A	0.9600
C2—C20	1.511 (3)	C22—H22B	0.9600
C3—C4	1.385 (3)	C22—H22C	0.9600
C3—H3A	0.9300	C23—H23A	0.9600
C4—C5	1.390 (3)	C23—H23B	0.9600
C4—H4A	0.9300	C23—H23C	0.9600
C5—C6	1.406 (3)	C22X—H22D	0.9600
C5—C21	1.515 (3)	C22X—H22E	0.9600
C7—C8	1.494 (3)	C22X—H22F	0.9600
C7—H7A	0.9700	C23X—H23D	0.9600
C7—H7B	0.9700	C23X—H23E	0.9600
C10—C11	1.513 (3)	C23X—H23F	0.9600
C10—H10A	0.9700	C24—H24A	0.9600
C10—H10B	0.9700	C24—H24B	0.9600
C11—C12	1.449 (3)	C24—H24C	0.9600
C12—C13	1.434 (3)
C9—S1—C10	93.77 (9)	C14—C15—H15A	120.7
C6—O1—C7	117.65 (16)	C16—C15—H15A	120.7
N5—O2—C13	111.22 (14)	C15—C16—C17	121.03 (19)
C8—N1—N2	107.70 (15)	C15—C16—H16A	119.5
C9—N2—N1	106.76 (15)	C17—C16—H16A	119.5
C9—N3—C8	105.11 (16)	C16—C17—C18	118.38 (18)
C9—N3—N4	129.02 (15)	C16—C17—C24	121.3 (2)
C8—N3—N4	124.59 (15)	C18—C17—C24	120.3 (2)
C11—N4—N3	115.09 (15)	C19—C18—C17	121.6 (2)
N6—N5—O2	105.30 (15)	C19—C18—H18A	119.2
N5—N6—C12	114.48 (16)	C17—C18—H18A	119.2
N5—N6—C14	113.81 (15)	C14—C19—C18	117.90 (18)
C12—N6—C14	131.68 (16)	C14—C19—H19A	121.0
C6—C1—C2	120.4 (2)	C18—C19—H19A	121.0
C6—C1—H1A	119.8	C2—C20—H20A	109.5
C2—C1—H1A	119.8	C2—C20—H20B	109.5
C3—C2—C1	118.3 (2)	H20A—C20—H20B	109.5
C3—C2—C20	121.42 (19)	C2—C20—H20C	109.5
C1—C2—C20	120.3 (2)	H20A—C20—H20C	109.5
C2—C3—C4	120.7 (2)	H20B—C20—H20C	109.5
C2—C3—H3A	119.7	C23X—C21—C5	115.5 (5)
C4—C3—H3A	119.7	C22—C21—C5	116.2 (3)
C3—C4—C5	122.6 (2)	C22—C21—C23	109.8 (4)
C3—C4—H4A	118.7	C5—C21—C23	107.9 (3)
C5—C4—H4A	118.7	C23X—C21—C22X	107.5 (8)
C4—C5—C6	115.9 (2)	C5—C21—C22X	103.8 (5)
C4—C5—C21	123.4 (2)	C22—C21—H21A	107.5
C6—C5—C21	120.61 (19)	C5—C21—H21A	107.5
O1—C6—C1	123.86 (18)	C23—C21—H21A	107.5
O1—C6—C5	114.11 (18)	C23X—C21—H21B	109.9
C1—C6—C5	122.03 (18)	C22—C21—H21B	131.2
O1—C7—C8	105.79 (16)	C5—C21—H21B	109.9
O1—C7—H7A	110.6	C23—C21—H21B	68.1
C8—C7—H7A	110.6	C22X—C21—H21B	109.9
O1—C7—H7B	110.6	C21—C22—H22A	109.5
C8—C7—H7B	110.6	C21—C22—H22B	109.5
H7A—C7—H7B	108.7	C21—C22—H22C	109.5
N1—C8—N3	109.95 (16)	C21—C23—H23A	109.5
N1—C8—C7	127.09 (17)	H21B—C23—H23A	94.7
N3—C8—C7	122.97 (17)	C21—C23—H23B	109.5
N2—C9—N3	110.46 (16)	H21B—C23—H23B	144.6
N2—C9—S1	129.40 (15)	C21—C23—H23C	109.5
N3—C9—S1	120.04 (14)	H21B—C23—H23C	85.0
C11—C10—S1	111.30 (13)	C21—C22X—H22D	109.5
C11—C10—H10A	109.4	C21—C22X—H22E	109.5
S1—C10—H10A	109.4	H22D—C22X—H22E	109.5
C11—C10—H10B	109.4	C21—C22X—H22F	109.5
S1—C10—H10B	109.4	H22D—C22X—H22F	109.5
H10A—C10—H10B	108.0	H22E—C22X—H22F	109.5
N4—C11—C12	119.20 (17)	C21—C23X—H23D	109.5
N4—C11—C10	123.66 (18)	C21—C23X—H23E	109.5
C12—C11—C10	117.04 (16)	H23D—C23X—H23E	109.5
N6—C12—C13	105.21 (16)	C21—C23X—H23F	109.5
N6—C12—C11	128.48 (17)	H23D—C23X—H23F	109.5
C13—C12—C11	126.00 (17)	H23E—C23X—H23F	109.5
O3—C13—O2	120.25 (17)	C17—C24—H24A	109.5
O3—C13—C12	135.99 (19)	C17—C24—H24B	109.5
O2—C13—C12	103.76 (16)	H24A—C24—H24B	109.5
C15—C14—C19	122.49 (17)	C17—C24—H24C	109.5
C15—C14—N6	118.37 (17)	H24A—C24—H24C	109.5
C19—C14—N6	118.95 (17)	H24B—C24—H24C	109.5
C14—C15—C16	118.53 (19)
C8—N1—N2—C9	0.3 (2)	N3—N4—C11—C10	−4.3 (3)
C9—N3—N4—C11	−27.6 (3)	S1—C10—C11—N4	47.2 (3)
C8—N3—N4—C11	167.24 (18)	S1—C10—C11—C12	−136.52 (16)
C13—O2—N5—N6	1.3 (2)	N5—N6—C12—C13	−0.9 (2)
O2—N5—N6—C12	−0.2 (2)	C14—N6—C12—C13	176.92 (19)
O2—N5—N6—C14	−178.43 (15)	N5—N6—C12—C11	172.90 (19)
C6—C1—C2—C3	−0.2 (3)	C14—N6—C12—C11	−9.3 (3)
C6—C1—C2—C20	−179.7 (2)	N4—C11—C12—N6	5.8 (3)
C1—C2—C3—C4	−0.2 (4)	C10—C11—C12—N6	−170.68 (19)
C20—C2—C3—C4	179.3 (2)	N4—C11—C12—C13	178.4 (2)
C2—C3—C4—C5	0.6 (4)	C10—C11—C12—C13	1.9 (3)
C3—C4—C5—C6	−0.5 (4)	N5—O2—C13—O3	178.29 (18)
C3—C4—C5—C21	176.9 (3)	N5—O2—C13—C12	−1.8 (2)
C7—O1—C6—C1	−5.2 (3)	N6—C12—C13—O3	−178.5 (2)
C7—O1—C6—C5	174.8 (2)	C11—C12—C13—O3	7.5 (4)
C2—C1—C6—O1	−179.7 (2)	N6—C12—C13—O2	1.5 (2)
C2—C1—C6—C5	0.3 (3)	C11—C12—C13—O2	−172.44 (19)
C4—C5—C6—O1	−180.0 (2)	N5—N6—C14—C15	−48.2 (2)
C21—C5—C6—O1	2.5 (3)	C12—N6—C14—C15	133.9 (2)
C4—C5—C6—C1	0.1 (3)	N5—N6—C14—C19	126.9 (2)
C21—C5—C6—C1	−177.4 (2)	C12—N6—C14—C19	−50.9 (3)
C6—O1—C7—C8	−177.50 (18)	C19—C14—C15—C16	2.5 (3)
N2—N1—C8—N3	−1.2 (2)	N6—C14—C15—C16	177.51 (18)
N2—N1—C8—C7	179.21 (18)	C14—C15—C16—C17	−0.8 (3)
C9—N3—C8—N1	1.5 (2)	C15—C16—C17—C18	−0.7 (3)
N4—N3—C8—N1	169.57 (17)	C15—C16—C17—C24	−178.7 (2)
C9—N3—C8—C7	−178.86 (18)	C16—C17—C18—C19	0.6 (3)
N4—N3—C8—C7	−10.8 (3)	C24—C17—C18—C19	178.7 (2)
O1—C7—C8—N1	−45.2 (3)	C15—C14—C19—C18	−2.6 (3)
O1—C7—C8—N3	135.22 (19)	N6—C14—C19—C18	−177.54 (17)
N1—N2—C9—N3	0.6 (2)	C17—C18—C19—C14	1.0 (3)
N1—N2—C9—S1	−175.78 (15)	C4—C5—C21—C23X	−43.8 (7)
C8—N3—C9—N2	−1.3 (2)	C6—C5—C21—C23X	133.5 (7)
N4—N3—C9—N2	−168.63 (17)	C4—C5—C21—C22	27.4 (5)
C8—N3—C9—S1	175.50 (14)	C6—C5—C21—C22	−155.2 (4)
N4—N3—C9—S1	8.1 (3)	C4—C5—C21—C23	−96.3 (3)
C10—S1—C9—N2	−154.3 (2)	C6—C5—C21—C23	81.0 (3)
C10—S1—C9—N3	29.67 (17)	C4—C5—C21—C22X	73.6 (6)
C9—S1—C10—C11	−51.92 (16)	C6—C5—C21—C22X	−109.1 (6)
N3—N4—C11—C12	179.41 (17)

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10B···O3	0.97	2.20	2.993 (3)	138
C10—H10A···N1i	0.97	2.56	3.393 (3)	144
C15—H15A···N2ii	0.93	2.49	3.377 (3)	160
C19—H19A···N2iii	0.93	2.47	3.397 (3)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10B⋯O3	0.97	2.20	2.993 (3)	138
C10—H10A⋯N1i	0.97	2.56	3.393 (3)	144
C15—H15A⋯N2ii	0.93	2.49	3.377 (3)	160
C19—H19A⋯N2iii	0.93	2.47	3.397 (3)	174

Symmetry codes: (i) ; (ii) ; (iii) .