3-[3-Methyl-4-(4-nitro-benzyl-idene-amino)-5-sulfanyl-idene-4,5-dihydro-1H-1,2,4-triazol-1-yl]-1,3-diphenyl-propan-1-one dichloro-methane monosolvate.

In the title compound, C(25)H(21)N(5)O(3)S·CH(2)Cl(2), the dichloro-methane solvent mol-ecule is disordered over four positions, with an occupancy ratio of 0.271 (3):0.3884 (18):0.298 (2):0.0424 (15). The 1,2,4-triazole ring makes dihedral angles of 47.3 (2)/87.3 (2) and 3.6 (2)° with the phenyl and nitro-phenyl rings, respectively. An intra-molecular C-H⋯S hydrogen bond results in the formation of an almost planar six-membered ring [r.m.s. derivation = 0.0051 (2) Å]. Inter-molecular C-H⋯O hydrogen bonding consolidates the structure.

Related literature

For crystal structures related to 1,2,4-triazole-5(4H)-thione, see: Al-Tamimi et al. (2010 ▶); Fun et al. (2009 ▶); Gao et al. (2011 ▶); Tan et al. (2010 ▶); Wang et al. (2011 ▶); Zhao et al. (2010 ▶).

Experimental

Crystal data

C25H21N5O3S·n class="Chemical">CH2Cl2

M = 556.45

Triclinic,

a = 8.9880 (13) Å

b = 11.4440 (15) Å

c = 14.8604 (18) Å

α = 70.212 (11)°

β = 88.973 (13)°

γ = 67.020 (9)°

V = 1312.6 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.37 mm−1

T = 113 K

0.26 × 0.24 × 0.20 mm

Data collection

Rigaku Saturn CCD diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005 ▶) T min = 0.911, T max = 0.931

16932 measured reflections

6203 independent reflections

4100 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.159

S = 1.07

6203 reflections

396 parameters

91 restraints

H-atom parameters constrained

Δρmax = 0.27 e Å−3

Δρmin = −0.41 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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: CrystalStructure (Rigaku/MSC, 2007 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811043777/zk2024sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811043777/zk2024Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811043777/zk2024Isup3.cml

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

C25H21N5O3S·CH2Cl2	Z = 2
Mr = 556.45	F(000) = 576
Triclinic, P1	Dx = 1.408 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.9880 (13) Å	Cell parameters from 4632 reflections
b = 11.4440 (15) Å	θ = 2.1–27.9°
c = 14.8604 (18) Å	µ = 0.37 mm−1
α = 70.212 (11)°	T = 113 K
β = 88.973 (13)°	Prism, colourless
γ = 67.020 (9)°	0.26 × 0.24 × 0.20 mm
V = 1312.6 (3) Å3

Rigaku Saturn CCD diffractometer	6203 independent reflections
Radiation source: rotating anode	4100 reflections with I > 2σ(I)
multilayer	Rint = 0.035
Detector resolution: 14.22 pixels mm-1	θmax = 27.9°, θmin = 2.1°
φ and ω scans	h = −11→11
Absorption correction: multi-scan (CrystalClear; Rigaku/MSC, 2005)	k = −15→15
Tmin = 0.911, Tmax = 0.931	l = −19→18
16932 measured reflections

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.159	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.0904P)2] where P = (Fo2 + 2Fc2)/3
6203 reflections	(Δ/σ)max = 0.003
396 parameters	Δρmax = 0.27 e Å−3
91 restraints	Δρmin = −0.41 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	Occ. (<1)
S1	0.48389 (7)	0.55051 (6)	0.09792 (4)	0.03327 (18)
O1	0.91577 (19)	0.35679 (16)	0.36980 (12)	0.0382 (4)
O2	−0.3675 (2)	0.7421 (2)	−0.32320 (14)	0.0570 (5)
O3	−0.5429 (2)	0.7897 (2)	−0.22653 (14)	0.0565 (5)
N1	0.4215 (2)	0.54864 (17)	0.27759 (11)	0.0220 (4)
N2	0.2982 (2)	0.57257 (18)	0.33400 (12)	0.0252 (4)
N4	0.0767 (2)	0.63610 (17)	0.12001 (12)	0.0253 (4)
N5	−0.4037 (3)	0.75374 (19)	−0.24612 (15)	0.0387 (5)
C1	1.0752 (3)	0.1110 (2)	0.52278 (17)	0.0316 (5)
H1	1.1363	0.1371	0.4730	0.038*
C2	1.1508 (3)	−0.0061 (2)	0.60281 (18)	0.0376 (6)
H2	1.2634	−0.0614	0.6072	0.045*
C3	1.0636 (3)	−0.0431 (2)	0.67630 (18)	0.0390 (6)
H3	1.1169	−0.1228	0.7316	0.047*
C4	0.8977 (3)	0.0356 (2)	0.67000 (17)	0.0401 (6)
H4	0.8377	0.0097	0.7206	0.048*
C5	0.8204 (3)	0.1531 (2)	0.58855 (16)	0.0320 (5)
H5	0.7072	0.2070	0.5835	0.038*
C6	0.9085 (2)	0.1913 (2)	0.51510 (15)	0.0262 (4)
C7	0.8314 (3)	0.3141 (2)	0.42531 (15)	0.0270 (5)
C8	0.6478 (2)	0.3800 (2)	0.40255 (15)	0.0270 (5)
H8A	0.5998	0.3976	0.4596	0.032*
H8B	0.6098	0.3167	0.3888	0.032*
C9	0.5887 (2)	0.5135 (2)	0.31618 (14)	0.0232 (4)
H9	0.6596	0.4983	0.2650	0.028*
C10	0.5934 (2)	0.6341 (2)	0.33558 (15)	0.0246 (4)
C11	0.5370 (3)	0.7600 (2)	0.25927 (17)	0.0331 (5)
H11	0.5027	0.7664	0.1970	0.040*
C12	0.5308 (3)	0.8754 (3)	0.2736 (2)	0.0440 (6)
H12	0.4908	0.9606	0.2217	0.053*
C13	0.5833 (3)	0.8658 (3)	0.3641 (2)	0.0469 (7)
H13	0.5785	0.9446	0.3743	0.056*
C14	0.6420 (3)	0.7426 (3)	0.43870 (19)	0.0406 (6)
H14	0.6787	0.7362	0.5004	0.049*
C15	0.6480 (3)	0.6268 (2)	0.42456 (16)	0.0284 (5)
H15	0.6902	0.5417	0.4766	0.034*
C16	0.3708 (2)	0.56787 (19)	0.18648 (14)	0.0228 (4)
N3	0.2032 (2)	0.60395 (16)	0.18804 (12)	0.0223 (4)
C17	0.1673 (2)	0.6053 (2)	0.27919 (14)	0.0249 (4)
C18	0.0009 (3)	0.6404 (3)	0.30726 (17)	0.0363 (5)
H18A	0.0046	0.6354	0.3744	0.054*
H18B	−0.0412	0.5762	0.3008	0.054*
H18C	−0.0707	0.7329	0.2652	0.054*
C19	0.1070 (3)	0.6337 (2)	0.03578 (15)	0.0275 (5)
H19	0.2148	0.6118	0.0195	0.033*
C20	−0.0282 (3)	0.6655 (2)	−0.03495 (15)	0.0264 (5)
C21	0.0061 (3)	0.6678 (2)	−0.12770 (16)	0.0303 (5)
H21	0.1140	0.6493	−0.1430	0.036*
C22	−0.1174 (3)	0.6972 (2)	−0.19751 (16)	0.0318 (5)
H22	−0.0955	0.6998	−0.2608	0.038*
C23	−0.2716 (3)	0.7224 (2)	−0.17278 (15)	0.0297 (5)
C24	−0.3097 (3)	0.7184 (2)	−0.08119 (16)	0.0324 (5)
H24	−0.4176	0.7352	−0.0662	0.039*
C25	−0.1863 (3)	0.6893 (2)	−0.01263 (16)	0.0311 (5)
H25	−0.2093	0.6855	0.0507	0.037*
Cl1	0.8120 (5)	1.0389 (4)	−0.0808 (3)	0.0362 (8)	0.271 (3)
Cl2	0.7811 (5)	1.0728 (4)	0.0934 (3)	0.0640 (12)	0.271 (3)
C26	0.6696 (14)	1.0852 (19)	−0.0030 (9)	0.094 (3)	0.271 (3)
H26A	0.5868	1.1794	−0.0348	0.112*	0.271 (3)
H26B	0.6137	1.0229	0.0170	0.112*	0.271 (3)
C27	0.7212 (11)	0.9953 (13)	0.0241 (7)	0.094 (3)	0.3884 (18)
H27A	0.7977	0.9021	0.0305	0.112*	0.3884 (18)
H27B	0.7413	1.0585	−0.0343	0.112*	0.3884 (18)
Cl3	0.5337 (2)	1.0078 (2)	0.00310 (16)	0.0435 (6)	0.3884 (18)
Cl4	0.7722 (3)	1.0250 (3)	0.11800 (18)	0.0621 (7)	0.3884 (18)
C28	0.9267 (13)	0.9766 (13)	0.0362 (7)	0.079 (4)	0.298 (2)
H28A	0.9329	0.8830	0.0550	0.095*	0.298 (2)
H28B	0.8410	1.0225	0.0705	0.095*	0.298 (2)
Cl6	1.1012 (7)	0.9588 (6)	0.0885 (4)	0.0887 (19)	0.298 (2)
Cl5	0.8513 (7)	1.0491 (5)	−0.0756 (4)	0.0586 (13)	0.298 (2)
Cl7	1.0305 (17)	0.9999 (14)	−0.0990 (9)	0.0362 (8)	0.0424 (15)
Cl8	1.176 (3)	1.000 (2)	0.0685 (12)	0.0362 (8)	0.0424 (15)
C29	1.185 (7)	0.908 (4)	−0.004 (4)	0.079 (4)	0.0424 (15)
H29A	1.2915	0.8843	−0.0290	0.095*	0.0424 (15)
H29B	1.1758	0.8219	0.0345	0.095*	0.0424 (15)

	U11	U22	U33	U12	U13	U23
S1	0.0257 (3)	0.0509 (4)	0.0245 (3)	−0.0139 (3)	0.0057 (2)	−0.0174 (3)
O1	0.0242 (8)	0.0376 (9)	0.0401 (9)	−0.0080 (7)	0.0043 (7)	−0.0043 (8)
O2	0.0592 (13)	0.0715 (13)	0.0390 (11)	−0.0221 (11)	−0.0150 (9)	−0.0229 (10)
O3	0.0368 (11)	0.0656 (13)	0.0511 (12)	−0.0185 (10)	−0.0200 (9)	−0.0036 (10)
N1	0.0193 (8)	0.0270 (9)	0.0185 (8)	−0.0089 (7)	0.0019 (6)	−0.0073 (7)
N2	0.0218 (8)	0.0323 (9)	0.0213 (8)	−0.0107 (7)	0.0031 (7)	−0.0098 (8)
N4	0.0229 (9)	0.0259 (9)	0.0234 (9)	−0.0079 (7)	−0.0056 (7)	−0.0065 (7)
N5	0.0428 (13)	0.0293 (10)	0.0365 (12)	−0.0141 (9)	−0.0164 (10)	−0.0029 (9)
C1	0.0258 (11)	0.0290 (11)	0.0397 (13)	−0.0120 (9)	−0.0047 (10)	−0.0106 (10)
C2	0.0275 (12)	0.0291 (12)	0.0502 (15)	−0.0093 (10)	−0.0122 (11)	−0.0088 (11)
C3	0.0400 (14)	0.0278 (12)	0.0373 (13)	−0.0088 (11)	−0.0169 (11)	−0.0024 (10)
C4	0.0469 (15)	0.0356 (13)	0.0289 (12)	−0.0140 (12)	−0.0045 (11)	−0.0039 (11)
C5	0.0299 (12)	0.0309 (11)	0.0284 (11)	−0.0067 (10)	−0.0033 (9)	−0.0090 (10)
C6	0.0241 (10)	0.0240 (10)	0.0291 (11)	−0.0086 (9)	−0.0046 (9)	−0.0092 (9)
C7	0.0244 (10)	0.0265 (10)	0.0292 (11)	−0.0091 (9)	0.0017 (9)	−0.0102 (9)
C8	0.0232 (10)	0.0259 (10)	0.0277 (11)	−0.0104 (9)	−0.0010 (8)	−0.0043 (9)
C9	0.0170 (9)	0.0270 (10)	0.0213 (10)	−0.0075 (8)	−0.0002 (8)	−0.0050 (8)
C10	0.0185 (9)	0.0289 (11)	0.0269 (10)	−0.0110 (8)	0.0031 (8)	−0.0090 (9)
C11	0.0350 (12)	0.0322 (12)	0.0311 (12)	−0.0174 (10)	−0.0005 (10)	−0.0058 (10)
C12	0.0467 (15)	0.0329 (13)	0.0494 (16)	−0.0211 (12)	0.0000 (12)	−0.0055 (12)
C13	0.0467 (15)	0.0402 (14)	0.0666 (19)	−0.0257 (12)	0.0034 (14)	−0.0248 (14)
C14	0.0380 (13)	0.0565 (16)	0.0431 (14)	−0.0270 (12)	0.0052 (11)	−0.0275 (13)
C15	0.0243 (10)	0.0351 (12)	0.0259 (11)	−0.0135 (9)	0.0025 (9)	−0.0095 (9)
C16	0.0223 (10)	0.0215 (10)	0.0231 (10)	−0.0084 (8)	−0.0002 (8)	−0.0068 (8)
N3	0.0202 (8)	0.0246 (9)	0.0206 (8)	−0.0082 (7)	0.0001 (7)	−0.0073 (7)
C17	0.0244 (10)	0.0293 (11)	0.0211 (10)	−0.0116 (9)	0.0029 (8)	−0.0083 (9)
C18	0.0237 (11)	0.0567 (15)	0.0323 (12)	−0.0167 (11)	0.0073 (9)	−0.0204 (12)
C19	0.0260 (11)	0.0267 (11)	0.0271 (11)	−0.0102 (9)	−0.0011 (9)	−0.0068 (9)
C20	0.0283 (11)	0.0227 (10)	0.0242 (10)	−0.0095 (9)	−0.0038 (9)	−0.0043 (9)
C21	0.0310 (11)	0.0334 (11)	0.0263 (11)	−0.0145 (10)	0.0004 (9)	−0.0088 (9)
C22	0.0378 (13)	0.0306 (11)	0.0243 (11)	−0.0139 (10)	−0.0026 (9)	−0.0063 (9)
C23	0.0349 (12)	0.0217 (10)	0.0256 (11)	−0.0105 (9)	−0.0122 (9)	−0.0007 (9)
C24	0.0265 (11)	0.0318 (12)	0.0346 (12)	−0.0101 (10)	−0.0023 (9)	−0.0088 (10)
C25	0.0299 (11)	0.0339 (12)	0.0254 (11)	−0.0113 (10)	−0.0012 (9)	−0.0078 (10)
Cl1	0.0368 (10)	0.0373 (10)	0.0345 (9)	−0.0143 (6)	0.0046 (6)	−0.0140 (6)
Cl2	0.0677 (15)	0.0600 (14)	0.0678 (15)	−0.0239 (10)	0.0039 (9)	−0.0294 (10)
C26	0.094 (3)	0.093 (3)	0.093 (3)	−0.0377 (14)	0.0128 (9)	−0.0339 (13)
C27	0.094 (3)	0.093 (3)	0.093 (3)	−0.0377 (14)	0.0128 (9)	−0.0339 (13)
Cl3	0.0459 (10)	0.0446 (8)	0.0421 (7)	−0.0168 (7)	0.0075 (8)	−0.0201 (6)
Cl4	0.0617 (10)	0.0766 (11)	0.0486 (10)	−0.0279 (8)	0.0057 (7)	−0.0234 (8)
C28	0.079 (4)	0.079 (4)	0.079 (4)	−0.0324 (16)	0.0104 (9)	−0.0286 (15)
Cl6	0.089 (2)	0.088 (2)	0.090 (2)	−0.0372 (12)	0.0078 (10)	−0.0314 (11)
Cl5	0.0574 (16)	0.0577 (15)	0.0607 (15)	−0.0229 (10)	0.0094 (10)	−0.0221 (10)
Cl7	0.0368 (10)	0.0373 (10)	0.0345 (9)	−0.0143 (6)	0.0046 (6)	−0.0140 (6)
Cl8	0.0368 (10)	0.0373 (10)	0.0345 (9)	−0.0143 (6)	0.0046 (6)	−0.0140 (6)
C29	0.079 (4)	0.079 (4)	0.079 (4)	−0.0324 (16)	0.0104 (9)	−0.0286 (15)

S1—C16	1.666 (2)	C14—C15	1.391 (3)
O1—C7	1.220 (3)	C14—H14	0.9500
O2—N5	1.221 (3)	C15—H15	0.9500
O3—N5	1.219 (3)	C16—N3	1.399 (2)
N1—C16	1.353 (2)	N3—C17	1.391 (2)
N1—N2	1.375 (2)	C17—C18	1.481 (3)
N1—C9	1.467 (2)	C18—H18A	0.9800
N2—C17	1.293 (3)	C18—H18B	0.9800
N4—C19	1.283 (3)	C18—H18C	0.9800
N4—N3	1.383 (2)	C19—C20	1.469 (3)
N5—C23	1.475 (3)	C19—H19	0.9500
C1—C2	1.383 (3)	C20—C25	1.394 (3)
C1—C6	1.401 (3)	C20—C21	1.401 (3)
C1—H1	0.9500	C21—C22	1.391 (3)
C2—C3	1.379 (4)	C21—H21	0.9500
C2—H2	0.9500	C22—C23	1.371 (3)
C3—C4	1.394 (4)	C22—H22	0.9500
C3—H3	0.9500	C23—C24	1.388 (3)
C4—C5	1.398 (3)	C24—C25	1.379 (3)
C4—H4	0.9500	C24—H24	0.9500
C5—C6	1.388 (3)	C25—H25	0.9500
C5—H5	0.9500	Cl1—C26	1.757 (9)
C6—C7	1.496 (3)	Cl2—C26	1.696 (9)
C7—C8	1.510 (3)	C26—H26A	0.9900
C8—C9	1.525 (3)	C26—H26B	0.9900
C8—H8A	0.9900	C27—Cl4	1.656 (8)
C8—H8B	0.9900	C27—Cl3	1.661 (8)
C9—C10	1.518 (3)	C27—H27A	0.9900
C9—H9	1.0000	C27—H27B	0.9900
C10—C15	1.383 (3)	C28—Cl5	1.606 (8)
C10—C11	1.401 (3)	C28—Cl6	1.671 (8)
C11—C12	1.388 (3)	C28—H28A	0.9900
C11—H11	0.9500	C28—H28B	0.9900
C12—C13	1.386 (4)	Cl7—C29	1.718 (11)
C12—H12	0.9500	Cl8—C29	1.723 (11)
C13—C14	1.370 (4)	C29—H29A	0.9900
C13—H13	0.9500	C29—H29B	0.9900
C16—N1—N2	113.97 (16)	N1—C16—S1	127.61 (15)
C16—N1—C9	125.89 (17)	N3—C16—S1	130.44 (15)
N2—N1—C9	120.04 (16)	N4—N3—C17	118.17 (16)
C17—N2—N1	105.18 (16)	N4—N3—C16	133.38 (17)
C19—N4—N3	119.39 (18)	C17—N3—C16	108.45 (16)
O3—N5—O2	123.6 (2)	N2—C17—N3	110.44 (18)
O3—N5—C23	118.3 (2)	N2—C17—C18	125.88 (19)
O2—N5—C23	118.2 (2)	N3—C17—C18	123.68 (18)
C2—C1—C6	120.0 (2)	C17—C18—H18A	109.5
C2—C1—H1	120.0	C17—C18—H18B	109.5
C6—C1—H1	120.0	H18A—C18—H18B	109.5
C3—C2—C1	120.3 (2)	C17—C18—H18C	109.5
C3—C2—H2	119.9	H18A—C18—H18C	109.5
C1—C2—H2	119.9	H18B—C18—H18C	109.5
C2—C3—C4	120.5 (2)	N4—C19—C20	118.7 (2)
C2—C3—H3	119.8	N4—C19—H19	120.7
C4—C3—H3	119.8	C20—C19—H19	120.7
C3—C4—C5	119.3 (2)	C25—C20—C21	119.3 (2)
C3—C4—H4	120.3	C25—C20—C19	122.8 (2)
C5—C4—H4	120.3	C21—C20—C19	117.8 (2)
C6—C5—C4	120.2 (2)	C22—C21—C20	120.2 (2)
C6—C5—H5	119.9	C22—C21—H21	119.9
C4—C5—H5	119.9	C20—C21—H21	119.9
C5—C6—C1	119.6 (2)	C23—C22—C21	118.4 (2)
C5—C6—C7	122.49 (19)	C23—C22—H22	120.8
C1—C6—C7	117.9 (2)	C21—C22—H22	120.8
O1—C7—C6	120.42 (19)	C22—C23—C24	123.1 (2)
O1—C7—C8	120.74 (19)	C22—C23—N5	118.9 (2)
C6—C7—C8	118.78 (18)	C24—C23—N5	118.0 (2)
C7—C8—C9	111.96 (17)	C25—C24—C23	118.0 (2)
C7—C8—H8A	109.2	C25—C24—H24	121.0
C9—C8—H8A	109.2	C23—C24—H24	121.0
C7—C8—H8B	109.2	C24—C25—C20	120.9 (2)
C9—C8—H8B	109.2	C24—C25—H25	119.5
H8A—C8—H8B	107.9	C20—C25—H25	119.5
N1—C9—C10	108.68 (16)	Cl2—C26—Cl1	104.9 (6)
N1—C9—C8	109.28 (16)	Cl2—C26—H26A	110.8
C10—C9—C8	115.60 (17)	Cl1—C26—H26A	110.8
N1—C9—H9	107.7	Cl2—C26—H26B	110.8
C10—C9—H9	107.7	Cl1—C26—H26B	110.8
C8—C9—H9	107.7	H26A—C26—H26B	108.8
C15—C10—C11	118.4 (2)	Cl4—C27—Cl3	119.9 (6)
C15—C10—C9	123.63 (18)	Cl4—C27—H27A	107.4
C11—C10—C9	118.01 (19)	Cl3—C27—H27A	107.3
C12—C11—C10	120.7 (2)	Cl4—C27—H27B	107.4
C12—C11—H11	119.6	Cl3—C27—H27B	107.4
C10—C11—H11	119.6	H27A—C27—H27B	106.9
C13—C12—C11	119.7 (2)	Cl5—C28—Cl6	128.9 (7)
C13—C12—H12	120.1	Cl5—C28—H28A	105.1
C11—C12—H12	120.1	Cl6—C28—H28A	105.1
C14—C13—C12	120.1 (2)	Cl5—C28—H28B	105.1
C14—C13—H13	120.0	Cl6—C28—H28B	105.1
C12—C13—H13	120.0	H28A—C28—H28B	105.9
C13—C14—C15	120.3 (2)	Cl7—C29—Cl8	110.7 (10)
C13—C14—H14	119.8	Cl7—C29—H29A	109.5
C15—C14—H14	119.8	Cl8—C29—H29A	109.5
C10—C15—C14	120.8 (2)	Cl7—C29—H29B	109.5
C10—C15—H15	119.6	Cl8—C29—H29B	109.5
C14—C15—H15	119.6	H29A—C29—H29B	108.1
N1—C16—N3	101.95 (16)
C16—N1—N2—C17	1.0 (2)	N2—N1—C16—N3	−1.2 (2)
C9—N1—N2—C17	177.73 (17)	C9—N1—C16—N3	−177.65 (17)
C6—C1—C2—C3	−1.3 (3)	N2—N1—C16—S1	179.26 (15)
C1—C2—C3—C4	1.2 (4)	C9—N1—C16—S1	2.8 (3)
C2—C3—C4—C5	−0.3 (4)	C19—N4—N3—C17	−179.04 (18)
C3—C4—C5—C6	−0.4 (4)	C19—N4—N3—C16	1.0 (3)
C4—C5—C6—C1	0.3 (3)	N1—C16—N3—N4	−179.15 (19)
C4—C5—C6—C7	178.5 (2)	S1—C16—N3—N4	0.4 (3)
C2—C1—C6—C5	0.5 (3)	N1—C16—N3—C17	0.9 (2)
C2—C1—C6—C7	−177.69 (19)	S1—C16—N3—C17	−179.57 (16)
C5—C6—C7—O1	168.2 (2)	N1—N2—C17—N3	−0.4 (2)
C1—C6—C7—O1	−13.7 (3)	N1—N2—C17—C18	179.9 (2)
C5—C6—C7—C8	−14.6 (3)	N4—N3—C17—N2	179.70 (17)
C1—C6—C7—C8	163.60 (19)	C16—N3—C17—N2	−0.3 (2)
O1—C7—C8—C9	−10.1 (3)	N4—N3—C17—C18	−0.5 (3)
C6—C7—C8—C9	172.62 (18)	C16—N3—C17—C18	179.4 (2)
C16—N1—C9—C10	111.5 (2)	N3—N4—C19—C20	178.82 (17)
N2—N1—C9—C10	−64.8 (2)	N4—C19—C20—C25	−4.4 (3)
C16—N1—C9—C8	−121.6 (2)	N4—C19—C20—C21	177.44 (19)
N2—N1—C9—C8	62.1 (2)	C25—C20—C21—C22	1.7 (3)
C7—C8—C9—N1	161.13 (17)	C19—C20—C21—C22	179.93 (19)
C7—C8—C9—C10	−75.9 (2)	C20—C21—C22—C23	−0.5 (3)
N1—C9—C10—C15	123.7 (2)	C21—C22—C23—C24	−0.7 (3)
C8—C9—C10—C15	0.4 (3)	C21—C22—C23—N5	179.95 (19)
N1—C9—C10—C11	−55.4 (2)	O3—N5—C23—C22	−172.5 (2)
C8—C9—C10—C11	−178.63 (18)	O2—N5—C23—C22	7.6 (3)
C15—C10—C11—C12	−2.3 (3)	O3—N5—C23—C24	8.2 (3)
C9—C10—C11—C12	176.8 (2)	O2—N5—C23—C24	−171.8 (2)
C10—C11—C12—C13	1.0 (4)	C22—C23—C24—C25	0.8 (3)
C11—C12—C13—C14	0.4 (4)	N5—C23—C24—C25	−179.88 (19)
C12—C13—C14—C15	−0.6 (4)	C23—C24—C25—C20	0.4 (3)
C11—C10—C15—C14	2.1 (3)	C21—C20—C25—C24	−1.6 (3)
C9—C10—C15—C14	−176.9 (2)	C19—C20—C25—C24	−179.8 (2)
C13—C14—C15—C10	−0.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C19—H19···S1	0.95	2.43	3.199 (3)	137
C18—H18B···O1i	0.98	2.55	3.443 (4)	152
C22—H22···O1ii	0.95	2.34	3.202 (3)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C19—H19⋯S1	0.95	2.43	3.199 (3)	137
C18—H18B⋯O1i	0.98	2.55	3.443 (4)	152
C22—H22⋯O1ii	0.95	2.34	3.202 (3)	151

Symmetry codes: (i) ; (ii) .