4-[(E)-4-Bromo-benzyl-ideneamino]-3-[1-(4-isobutyl-phen-yl)eth-yl]-1H-1,2,4-triazole-5(4H)-thione.

In the title compound, C(21)H(23)BrN(4)S, the 4-bromo-benzyl-idene group is disordered over two orientations with occupancies of 0.504 (5) and 0.496 (5). One of the methyl groups of the isobutyl unit is disordered over two sites with occupancies of 0.751 (19) and 0.249 (19). The benzene rings of the isobutylphenyl and bromo-phenyl (major disorder component) groups form dihedral angles of 71.63 (11) and 21.8 (3)°, respectively, with the triazole ring. In the crystal, centrosymmetrically related mol-ecules exist as centrosymmetric N-H⋯S hydrogen-bonded dimers.

Related literature

For the pharmaceutical applications of triazole derivatives, see: Al-Soud et al. (2003 ▶); Almasirad et al. (2004 ▶); Amir & Shikha (2004 ▶); Demirbas et al. (2004 ▶); Holla et al. (2003 ▶); Kawashima et al. (1987 ▶); Zitouni et al. (2005 ▶); Walczak et al. (2004 ▶); For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Fun et al. (2008a ▶,b ▶). For the stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C21H23BrN4S

M = 443.40

Triclinic,

a = 5.5791 (2) Å

b = 11.3052 (3) Å

c = 17.3688 (4) Å

α = 75.421 (1)°

β = 86.614 (1)°

γ = 79.616 (1)°

V = 1042.75 (5) Å3

Z = 2

Mo Kα radiation

μ = 2.08 mm−1

T = 100 K

0.27 × 0.17 × 0.05 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.602, T max = 0.908

26698 measured reflections

8529 independent reflections

5907 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.141

S = 1.05

8529 reflections

331 parameters

44 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.67 e Å−3

Δρmin = −0.83 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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/S1600536809018030/ci2795sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809018030/ci2795Isup2.hkl

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

C21H23BrN4S	Z = 2
Mr = 443.40	F(000) = 456
Triclinic, P1	Dx = 1.412 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.5791 (2) Å	Cell parameters from 9940 reflections
b = 11.3052 (3) Å	θ = 2.7–33.0°
c = 17.3688 (4) Å	µ = 2.08 mm−1
α = 75.421 (1)°	T = 100 K
β = 86.614 (1)°	Plate, colourless
γ = 79.616 (1)°	0.27 × 0.17 × 0.05 mm
V = 1042.75 (5) Å3

Bruker SMART APEXII CCD area-detector diffractometer	8529 independent reflections
Radiation source: fine-focus sealed tube	5907 reflections with I > 2σ(I)
graphite	Rint = 0.029
φ and ω scans	θmax = 34.2°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→8
Tmin = 0.602, Tmax = 0.908	k = −17→17
26698 measured reflections	l = −27→27

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) = 0.141	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0732P)2 + 0.4173P] where P = (Fo2 + 2Fc2)/3
8529 reflections	(Δ/σ)max = 0.001
331 parameters	Δρmax = 0.67 e Å−3
44 restraints	Δρmin = −0.83 e Å−3

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

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	1.28609 (9)	0.34264 (4)	0.51104 (3)	0.01997 (11)
N1	1.3036 (3)	0.56195 (15)	0.40486 (11)	0.0218 (3)
N2	1.1990 (3)	0.64191 (15)	0.33670 (10)	0.0210 (3)
N3	1.0344 (3)	0.47201 (14)	0.37298 (10)	0.0179 (3)
N4	0.8770 (3)	0.39601 (15)	0.36230 (10)	0.0207 (3)
Br1A	0.3846 (3)	−0.10655 (16)	0.32563 (14)	0.0250 (2)	0.504 (5)
C1A	0.6489 (11)	0.2199 (4)	0.3123 (3)	0.0230 (10)	0.504 (5)
H1A	0.6584	0.2931	0.2740	0.028*	0.504 (5)
C2A	0.5425 (10)	0.1269 (4)	0.2937 (3)	0.0257 (10)	0.504 (5)
H2A	0.4850	0.1376	0.2428	0.031*	0.504 (5)
C3A	0.524 (3)	0.0185 (11)	0.3521 (7)	0.023 (2)	0.504 (5)
C4A	0.6099 (8)	0.0001 (3)	0.4279 (2)	0.0222 (9)	0.504 (5)
H4A	0.5976	−0.0728	0.4661	0.027*	0.504 (5)
C5A	0.7157 (8)	0.0922 (3)	0.4464 (2)	0.0200 (8)	0.504 (5)
H5A	0.7704	0.0804	0.4977	0.024*	0.504 (5)
C6A	0.7418 (14)	0.2021 (7)	0.3895 (4)	0.0140 (13)	0.504 (5)
C7A	0.9410 (9)	0.2829 (4)	0.3857 (3)	0.0164 (8)	0.504 (5)
H7A	1.1007	0.2478	0.4003	0.020*	0.504 (5)
Br1B	0.3266 (4)	−0.0828 (2)	0.32652 (14)	0.0315 (3)	0.496 (5)
C1B	0.5581 (10)	0.2422 (5)	0.3354 (4)	0.0251 (10)	0.496 (5)
H1B	0.4996	0.3270	0.3207	0.030*	0.496 (5)
C2B	0.4229 (9)	0.1591 (4)	0.3211 (3)	0.0259 (10)	0.496 (5)
H2B	0.2742	0.1874	0.2955	0.031*	0.496 (5)
C3B	0.511 (2)	0.0331 (10)	0.3453 (7)	0.019 (2)	0.496 (5)
C4B	0.7310 (8)	−0.0122 (4)	0.3842 (3)	0.0227 (9)	0.496 (5)
H4B	0.7865	−0.0972	0.4007	0.027*	0.496 (5)
C5B	0.8665 (7)	0.0715 (3)	0.3982 (2)	0.0205 (9)	0.496 (5)
H5B	1.0132	0.0433	0.4250	0.025*	0.496 (5)
C6B	0.7815 (16)	0.1976 (8)	0.3717 (4)	0.0177 (15)	0.496 (5)
C7B	0.8642 (10)	0.2913 (4)	0.4107 (3)	0.0195 (9)	0.496 (5)
H7B	0.9015	0.2734	0.4643	0.023*	0.496 (5)
C8	1.2086 (4)	0.45804 (17)	0.42984 (11)	0.0183 (3)
C9	1.0332 (4)	0.58544 (17)	0.31907 (12)	0.0186 (3)
C10	0.8618 (4)	0.63522 (17)	0.25106 (11)	0.0182 (3)
H10	0.6956	0.6424	0.2732	0.022*
C11	0.8818 (3)	0.55032 (17)	0.19481 (11)	0.0182 (3)
C12	0.6815 (4)	0.55549 (18)	0.14931 (12)	0.0202 (4)
H12	0.5389	0.6103	0.1541	0.024*
C13	0.6911 (4)	0.48005 (19)	0.09682 (12)	0.0231 (4)
H13	0.5545	0.4853	0.0671	0.028*
C14	0.9017 (4)	0.39637 (18)	0.08781 (12)	0.0216 (4)
C15	1.1011 (4)	0.3927 (2)	0.13315 (14)	0.0248 (4)
H15	1.2441	0.3382	0.1283	0.030*
C16	1.0928 (4)	0.46833 (19)	0.18572 (13)	0.0236 (4)
H16	1.2299	0.4639	0.2150	0.028*
C17	0.9038 (5)	0.3124 (2)	0.03308 (14)	0.0269 (4)
H17A	1.0714	0.2834	0.0194	0.032*
H17B	0.8221	0.3598	−0.0157	0.032*
C18	0.7800 (5)	0.1999 (2)	0.06865 (16)	0.0336 (5)
H18A	0.6260	0.2265	0.0946	0.040*	0.751 (19)
H18B	0.6190	0.2385	0.0806	0.040*	0.249 (19)
C19	0.9578 (16)	0.1074 (4)	0.1326 (3)	0.0482 (17)	0.751 (19)
H19A	0.8860	0.0355	0.1564	0.072*	0.751 (19)
H19B	0.9859	0.1477	0.1729	0.072*	0.751 (19)
H19C	1.1099	0.0828	0.1074	0.072*	0.751 (19)
C19A	0.833 (5)	0.1155 (12)	0.1451 (7)	0.045 (4)	0.249 (19)
H19D	0.6845	0.1088	0.1756	0.068*	0.249 (19)
H19E	0.9431	0.1459	0.1728	0.068*	0.249 (19)
H19F	0.9065	0.0353	0.1380	0.068*	0.249 (19)
C20	0.7304 (6)	0.1367 (3)	0.0047 (2)	0.0443 (7)
H20A	0.6351	0.1960	−0.0366	0.066*
H20B	0.6427	0.0703	0.0278	0.066*
H20C	0.8823	0.1040	−0.0174	0.066*
C21	0.9022 (5)	0.76614 (19)	0.20644 (14)	0.0282 (4)
H21A	0.8821	0.8187	0.2428	0.042*
H21B	0.7857	0.7995	0.1646	0.042*
H21C	1.0640	0.7620	0.1840	0.042*
H1N1	1.424 (7)	0.584 (4)	0.429 (2)	0.058 (10)*

	U11	U22	U33	U12	U13	U23
S1	0.0262 (2)	0.01396 (19)	0.0200 (2)	−0.00712 (16)	−0.00585 (17)	−0.00092 (16)
N1	0.0275 (8)	0.0159 (7)	0.0224 (8)	−0.0096 (6)	−0.0078 (7)	0.0004 (6)
N2	0.0268 (8)	0.0164 (7)	0.0200 (8)	−0.0085 (6)	−0.0040 (6)	−0.0006 (6)
N3	0.0230 (7)	0.0137 (7)	0.0179 (7)	−0.0067 (6)	−0.0035 (6)	−0.0022 (5)
N4	0.0228 (8)	0.0146 (7)	0.0244 (8)	−0.0080 (6)	−0.0057 (6)	0.0001 (6)
Br1A	0.0305 (6)	0.0176 (4)	0.0322 (3)	−0.0109 (3)	−0.0032 (4)	−0.0103 (3)
C1A	0.032 (3)	0.019 (2)	0.018 (2)	−0.0129 (19)	−0.0069 (18)	0.0021 (15)
C2A	0.035 (3)	0.0224 (19)	0.023 (2)	−0.0130 (18)	−0.0103 (19)	−0.0035 (16)
C3A	0.026 (4)	0.011 (2)	0.030 (4)	−0.004 (2)	0.005 (3)	−0.001 (2)
C4A	0.033 (2)	0.0124 (15)	0.0231 (19)	−0.0097 (14)	−0.0019 (17)	−0.0024 (13)
C5A	0.029 (2)	0.0126 (15)	0.0186 (17)	−0.0080 (13)	−0.0031 (14)	−0.0011 (13)
C6A	0.023 (3)	0.0115 (19)	0.009 (3)	−0.0039 (17)	−0.003 (2)	−0.0036 (19)
C7A	0.021 (2)	0.0120 (16)	0.017 (2)	−0.0037 (15)	−0.0023 (16)	−0.0046 (15)
Br1B	0.0392 (8)	0.0315 (8)	0.0318 (3)	−0.0229 (5)	−0.0061 (6)	−0.0093 (5)
C1B	0.022 (2)	0.021 (2)	0.033 (3)	−0.0042 (18)	−0.008 (2)	−0.0075 (19)
C2B	0.022 (2)	0.027 (2)	0.033 (2)	−0.0072 (17)	−0.0047 (18)	−0.0108 (18)
C3B	0.026 (4)	0.022 (4)	0.017 (3)	−0.014 (3)	−0.006 (2)	−0.010 (3)
C4B	0.027 (2)	0.0158 (17)	0.027 (2)	−0.0086 (14)	−0.0062 (17)	−0.0043 (15)
C5B	0.0243 (18)	0.0125 (15)	0.025 (2)	−0.0066 (13)	−0.0076 (15)	−0.0015 (13)
C6B	0.029 (3)	0.015 (2)	0.012 (3)	−0.0049 (19)	0.003 (2)	−0.009 (2)
C7B	0.025 (2)	0.0170 (19)	0.017 (2)	−0.0063 (17)	−0.0018 (17)	−0.0023 (16)
C8	0.0234 (9)	0.0144 (7)	0.0178 (8)	−0.0060 (6)	−0.0032 (7)	−0.0027 (6)
C9	0.0238 (9)	0.0130 (7)	0.0187 (8)	−0.0062 (6)	−0.0014 (7)	−0.0011 (6)
C10	0.0219 (8)	0.0130 (7)	0.0188 (8)	−0.0040 (6)	−0.0035 (7)	−0.0006 (6)
C11	0.0196 (8)	0.0144 (7)	0.0191 (8)	−0.0051 (6)	−0.0027 (6)	0.0004 (6)
C12	0.0208 (8)	0.0159 (8)	0.0228 (9)	0.0005 (6)	−0.0046 (7)	−0.0044 (7)
C13	0.0260 (9)	0.0210 (9)	0.0215 (9)	−0.0051 (7)	−0.0066 (7)	−0.0020 (7)
C14	0.0273 (9)	0.0173 (8)	0.0206 (9)	−0.0076 (7)	0.0028 (7)	−0.0032 (7)
C15	0.0192 (9)	0.0219 (9)	0.0329 (11)	−0.0015 (7)	0.0022 (8)	−0.0081 (8)
C16	0.0182 (8)	0.0233 (9)	0.0299 (10)	−0.0040 (7)	−0.0021 (7)	−0.0071 (8)
C17	0.0367 (11)	0.0202 (9)	0.0252 (10)	−0.0054 (8)	0.0016 (9)	−0.0082 (8)
C18	0.0443 (13)	0.0196 (10)	0.0392 (13)	−0.0108 (9)	0.0066 (11)	−0.0091 (9)
C19	0.064 (4)	0.0223 (16)	0.052 (2)	−0.0045 (18)	−0.012 (2)	0.0026 (15)
C19A	0.058 (6)	0.035 (5)	0.045 (5)	−0.015 (4)	0.010 (4)	−0.011 (4)
C20	0.0526 (17)	0.0268 (12)	0.0591 (18)	−0.0079 (11)	−0.0076 (14)	−0.0186 (12)
C21	0.0406 (12)	0.0167 (9)	0.0258 (10)	−0.0076 (8)	−0.0073 (9)	0.0011 (7)

S1—C8	1.6794 (19)	C9—C10	1.494 (3)
N1—C8	1.338 (2)	C10—C11	1.520 (3)
N1—N2	1.383 (2)	C10—C21	1.538 (3)
N1—H1N1	0.91 (4)	C10—H10	0.98
N2—C9	1.305 (2)	C11—C16	1.389 (3)
N3—C9	1.384 (2)	C11—C12	1.391 (3)
N3—N4	1.384 (2)	C12—C13	1.389 (3)
N3—C8	1.387 (2)	C12—H12	0.93
N4—C7A	1.232 (5)	C13—C14	1.398 (3)
N4—C7B	1.279 (5)	C13—H13	0.93
Br1A—C3A	1.891 (13)	C14—C15	1.389 (3)
C1A—C2A	1.408 (5)	C14—C17	1.501 (3)
C1A—C6A	1.419 (7)	C15—C16	1.393 (3)
C1A—H1A	0.93	C15—H15	0.93
C2A—C3A	1.397 (11)	C16—H16	0.93
C2A—H2A	0.93	C17—C18	1.533 (3)
C3A—C4A	1.381 (11)	C17—H17A	0.97
C4A—C5A	1.395 (5)	C17—H17B	0.97
C4A—H4A	0.93	C18—C19A	1.438 (12)
C5A—C6A	1.405 (8)	C18—C20	1.526 (4)
C5A—H5A	0.93	C18—C19	1.576 (5)
C6A—C7A	1.549 (8)	C18—H18A	0.98
C7A—H7A	0.93	C18—H18B	0.96
Br1B—C3B	1.903 (10)	C19—H19A	0.96
C1B—C2B	1.381 (6)	C19—H19B	0.96
C1B—C6B	1.383 (9)	C19—H19C	0.96
C1B—H1B	0.93	C19A—H19D	0.96
C2B—C3B	1.385 (10)	C19A—H19E	0.96
C2B—H2B	0.93	C19A—H19F	0.96
C3B—C4B	1.386 (10)	C20—H20A	0.96
C4B—C5B	1.386 (5)	C20—H20B	0.96
C4B—H4B	0.93	C20—H20C	0.96
C5B—C6B	1.386 (9)	C21—H21A	0.96
C5B—H5B	0.93	C21—H21B	0.96
C6B—C7B	1.538 (9)	C21—H21C	0.96
C7B—H7B	0.93
C8—N1—N2	114.19 (16)	C21—C10—H10	107.6
C8—N1—H1N1	126 (2)	C16—C11—C12	118.05 (18)
N2—N1—H1N1	120 (2)	C16—C11—C10	123.04 (17)
C9—N2—N1	104.04 (15)	C12—C11—C10	118.90 (17)
C9—N3—N4	119.15 (15)	C13—C12—C11	121.08 (19)
C9—N3—C8	108.45 (15)	C13—C12—H12	119.5
N4—N3—C8	132.40 (15)	C11—C12—H12	119.5
C7A—N4—N3	118.1 (3)	C12—C13—C14	121.30 (18)
C7B—N4—N3	122.6 (3)	C12—C13—H13	119.3
C2A—C1A—C6A	120.1 (5)	C14—C13—H13	119.3
C2A—C1A—H1A	119.9	C15—C14—C13	117.07 (19)
C6A—C1A—H1A	119.9	C15—C14—C17	122.7 (2)
C3A—C2A—C1A	119.6 (6)	C13—C14—C17	120.17 (19)
C3A—C2A—H2A	120.2	C14—C15—C16	121.89 (19)
C1A—C2A—H2A	120.2	C14—C15—H15	119.1
C4A—C3A—C2A	121.2 (9)	C16—C15—H15	119.1
C4A—C3A—Br1A	119.7 (7)	C11—C16—C15	120.60 (19)
C2A—C3A—Br1A	119.1 (7)	C11—C16—H16	119.7
C3A—C4A—C5A	119.2 (6)	C15—C16—H16	119.7
C3A—C4A—H4A	120.4	C14—C17—C18	113.68 (19)
C5A—C4A—H4A	120.4	C14—C17—H17A	108.8
C4A—C5A—C6A	121.8 (4)	C18—C17—H17A	108.8
C4A—C5A—H5A	119.1	C14—C17—H17B	108.8
C6A—C5A—H5A	119.1	C18—C17—H17B	108.8
C5A—C6A—C1A	118.1 (6)	H17A—C17—H17B	107.7
C5A—C6A—C7A	127.4 (6)	C19A—C18—C20	113.6 (6)
C1A—C6A—C7A	109.9 (5)	C19A—C18—C17	125.0 (8)
N4—C7A—C6A	116.6 (5)	C20—C18—C17	111.2 (2)
N4—C7A—H7A	121.7	C20—C18—C19	110.1 (3)
C6A—C7A—H7A	121.7	C17—C18—C19	107.0 (3)
C2B—C1B—C6B	119.2 (5)	C19A—C18—H18A	83.7
C2B—C1B—H1B	120.4	C20—C18—H18A	109.5
C6B—C1B—H1B	120.4	C17—C18—H18A	109.5
C1B—C2B—C3B	119.3 (5)	C19—C18—H18A	109.5
C1B—C2B—H2B	120.3	C19A—C18—H18B	98.3
C3B—C2B—H2B	120.3	C20—C18—H18B	101.9
C2B—C3B—C4B	121.8 (7)	C17—C18—H18B	102.0
C2B—C3B—Br1B	119.9 (6)	C19—C18—H18B	124.2
C4B—C3B—Br1B	118.3 (7)	C18—C19—H19A	109.5
C5B—C4B—C3B	118.7 (5)	C18—C19—H19B	109.5
C5B—C4B—H4B	120.6	H19A—C19—H19B	109.5
C3B—C4B—H4B	120.6	C18—C19—H19C	109.5
C6B—C5B—C4B	119.4 (5)	H19A—C19—H19C	109.5
C6B—C5B—H5B	120.3	H19B—C19—H19C	109.5
C4B—C5B—H5B	120.3	C18—C19A—H19D	109.5
C1B—C6B—C5B	121.5 (7)	C18—C19A—H19E	109.5
C1B—C6B—C7B	112.5 (6)	H19D—C19A—H19E	109.5
C5B—C6B—C7B	121.0 (6)	C18—C19A—H19F	109.5
N4—C7B—C6B	113.6 (5)	H19D—C19A—H19F	109.5
N4—C7B—H7B	123.2	H19E—C19A—H19F	109.5
C6B—C7B—H7B	123.2	C18—C20—H20A	109.5
N1—C8—N3	102.67 (15)	C18—C20—H20B	109.5
N1—C8—S1	127.12 (15)	H20A—C20—H20B	109.5
N3—C8—S1	130.21 (14)	C18—C20—H20C	109.5
N2—C9—N3	110.62 (17)	H20A—C20—H20C	109.5
N2—C9—C10	125.50 (16)	H20B—C20—H20C	109.5
N3—C9—C10	123.88 (16)	C10—C21—H21A	109.5
C9—C10—C11	112.76 (16)	C10—C21—H21B	109.5
C9—C10—C21	109.82 (16)	H21A—C21—H21B	109.5
C11—C10—C21	111.13 (17)	C10—C21—H21C	109.5
C9—C10—H10	107.6	H21A—C21—H21C	109.5
C11—C10—H10	107.6	H21B—C21—H21C	109.5
C8—N1—N2—C9	0.1 (2)	N2—N1—C8—S1	−178.50 (16)
C9—N3—N4—C7A	149.7 (3)	C9—N3—C8—N1	−1.7 (2)
C8—N3—N4—C7A	−29.4 (4)	N4—N3—C8—N1	177.6 (2)
C9—N3—N4—C7B	−178.4 (4)	C9—N3—C8—S1	177.80 (17)
C8—N3—N4—C7B	2.4 (5)	N4—N3—C8—S1	−2.9 (3)
C6A—C1A—C2A—C3A	1.5 (12)	N1—N2—C9—N3	−1.2 (2)
C1A—C2A—C3A—C4A	−0.6 (17)	N1—N2—C9—C10	178.08 (19)
C1A—C2A—C3A—Br1A	−179.1 (7)	N4—N3—C9—N2	−177.49 (17)
C2A—C3A—C4A—C5A	0.6 (16)	C8—N3—C9—N2	1.9 (2)
Br1A—C3A—C4A—C5A	179.0 (6)	N4—N3—C9—C10	3.2 (3)
C3A—C4A—C5A—C6A	−1.4 (11)	C8—N3—C9—C10	−177.41 (19)
C4A—C5A—C6A—C1A	2.2 (9)	N2—C9—C10—C11	122.2 (2)
C4A—C5A—C6A—C7A	−150.8 (6)	N3—C9—C10—C11	−58.6 (3)
C2A—C1A—C6A—C5A	−2.3 (10)	N2—C9—C10—C21	−2.3 (3)
C2A—C1A—C6A—C7A	155.2 (6)	N3—C9—C10—C21	176.8 (2)
C7B—N4—C7A—C6A	60.1 (8)	C9—C10—C11—C16	−26.2 (3)
N3—N4—C7A—C6A	167.3 (4)	C21—C10—C11—C16	97.6 (2)
C5A—C6A—C7A—N4	−143.9 (6)	C9—C10—C11—C12	154.71 (18)
C1A—C6A—C7A—N4	61.2 (8)	C21—C10—C11—C12	−81.5 (2)
C6B—C1B—C2B—C3B	1.6 (11)	C16—C11—C12—C13	0.6 (3)
C1B—C2B—C3B—C4B	0.6 (16)	C10—C11—C12—C13	179.79 (18)
C1B—C2B—C3B—Br1B	179.7 (7)	C11—C12—C13—C14	0.0 (3)
C2B—C3B—C4B—C5B	−0.8 (15)	C12—C13—C14—C15	−0.4 (3)
Br1B—C3B—C4B—C5B	180.0 (6)	C12—C13—C14—C17	177.59 (19)
C3B—C4B—C5B—C6B	−1.1 (10)	C13—C14—C15—C16	0.3 (3)
C2B—C1B—C6B—C5B	−3.7 (10)	C17—C14—C15—C16	−177.7 (2)
C2B—C1B—C6B—C7B	−158.9 (6)	C12—C11—C16—C15	−0.8 (3)
C4B—C5B—C6B—C1B	3.4 (9)	C10—C11—C16—C15	−179.91 (19)
C4B—C5B—C6B—C7B	156.6 (6)	C14—C15—C16—C11	0.3 (3)
C7A—N4—C7B—C6B	−63.2 (8)	C15—C14—C17—C18	99.4 (3)
N3—N4—C7B—C6B	−152.4 (4)	C13—C14—C17—C18	−78.5 (3)
C1B—C6B—C7B—N4	−57.0 (8)	C14—C17—C18—C19A	−51.5 (11)
C5B—C6B—C7B—N4	147.5 (6)	C14—C17—C18—C20	165.7 (2)
N2—N1—C8—N3	1.0 (2)	C14—C17—C18—C19	−74.0 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···S1i	0.91 (4)	2.35 (4)	3.2582 (18)	175 (4)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯S1i	0.91 (4)	2.35 (4)	3.2582 (18)	175 (4)

Symmetry code: (i) .