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

In the title compound, C(34)H(34)BrN(5)S, the two phenyl rings of the diphenyl-amino-methyl group are inclined at an angle of 73.86 (8)° and they form dihedral angles of 74.04 (8) and 48.74 (8)° with the triazole ring. Intra-molecular C-H⋯S hydrogen bonds generate S(6) and S(5) ring motifs. The crystal structure is stabilized by weak C-H⋯π inter-actions.

Related literature

For related literature, see: Dave et al. (2007 ▶); Kalluraya et al. (2003 ▶, 2004 ▶, 2007 ▶); Kane et al. (1990 ▶). For literature on Mannich bases, see: Kalluraya et al. (2001 ▶). For bond-length data, see: Allen et al. (1987 ▶). For related literature on hydrogen-bond motifs, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C34H34BrN5S

M = 624.63

Monoclinic,

a = 10.9672 (1) Å

b = 9.7833 (1) Å

c = 28.6210 (3) Å

β = 105.966 (1)°

V = 2952.44 (5) Å3

Z = 4

Mo Kα radiation

μ = 1.50 mm−1

T = 100.0 (1) K

0.35 × 0.31 × 0.27 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.623, T max = 0.684

55283 measured reflections

13248 independent reflections

7914 reflections with I > 2σ(I)

R int = 0.059

Refinement

R[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.098

S = 1.01

13248 reflections

372 parameters

H-atom parameters constrained

Δρmax = 0.46 e Å−3

Δρmin = −0.57 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); 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, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808012713/ci2592sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808012713/ci2592Isup2.hkl

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

C34H34BrN5S	F000 = 1296
Mr = 624.63	Dx = 1.405 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8665 reflections
a = 10.9672 (1) Å	θ = 2.2–29.2º
b = 9.7833 (1) Å	µ = 1.50 mm−1
c = 28.6210 (3) Å	T = 100.0 (1) K
β = 105.966 (1)º	Block, colourless
V = 2952.44 (5) Å3	0.35 × 0.31 × 0.27 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	13248 independent reflections
Radiation source: fine-focus sealed tube	7914 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.059
T = 100.0(1) K	θmax = 35.4º
φ and ω scans	θmin = 1.9º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −17→17
Tmin = 0.623, Tmax = 0.684	k = −15→15
55283 measured reflections	l = −46→46

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.044	H-atom parameters constrained
wR(F2) = 0.098	w = 1/[σ2(Fo2) + (0.0352P)2 + 0.5449P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
13248 reflections	Δρmax = 0.46 e Å−3
372 parameters	Δρmin = −0.57 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. The data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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
Br1	0.543981 (15)	−0.004817 (17)	−0.133261 (6)	0.02529 (5)
S1	0.15515 (5)	−0.27622 (4)	0.091481 (16)	0.02758 (10)
N1	0.11707 (12)	−0.00549 (12)	0.06174 (4)	0.0177 (2)
N2	0.01822 (12)	0.07970 (13)	0.11283 (5)	0.0194 (3)
N3	0.05163 (13)	−0.05530 (13)	0.12340 (4)	0.0192 (3)
N4	0.05997 (13)	−0.03122 (13)	0.20801 (5)	0.0213 (3)
N5	0.16650 (12)	0.00579 (12)	0.02217 (4)	0.0186 (2)
C1	0.11076 (15)	−0.11338 (15)	0.09263 (5)	0.0194 (3)
C2	0.05841 (14)	0.10666 (15)	0.07525 (5)	0.0176 (3)
C3	0.25133 (14)	−0.08055 (15)	0.01851 (5)	0.0191 (3)
H3A	0.2737	−0.1521	0.0406	0.023*
C4	0.31254 (14)	−0.06601 (15)	−0.02038 (5)	0.0170 (3)
C5	0.41316 (15)	−0.15262 (15)	−0.02088 (5)	0.0193 (3)
H5A	0.4342	−0.2231	0.0017	0.023*
C6	0.48243 (15)	−0.13606 (15)	−0.05424 (5)	0.0194 (3)
H6A	0.5502	−0.1935	−0.0539	0.023*
C7	0.44857 (15)	−0.03203 (15)	−0.08809 (5)	0.0194 (3)
C8	0.34706 (15)	0.05398 (16)	−0.08930 (5)	0.0202 (3)
H8A	0.3250	0.1224	−0.1127	0.024*
C9	0.27910 (15)	0.03763 (15)	−0.05571 (5)	0.0195 (3)
H9A	0.2111	0.0951	−0.0564	0.023*
C10	0.04978 (14)	0.24247 (15)	0.05043 (5)	0.0196 (3)
H10A	0.0236	0.2270	0.0152	0.023*
C11	0.17723 (14)	0.31489 (14)	0.06341 (5)	0.0181 (3)
C12	0.21998 (15)	0.37842 (15)	0.02736 (5)	0.0203 (3)
H12A	0.1743	0.3683	−0.0050	0.024*
C13	0.32967 (16)	0.45656 (16)	0.03905 (6)	0.0220 (3)
H13A	0.3565	0.4979	0.0143	0.026*
C14	0.40058 (15)	0.47425 (15)	0.08733 (6)	0.0198 (3)
C15	0.35851 (15)	0.40810 (16)	0.12319 (6)	0.0218 (3)
H15A	0.4047	0.4170	0.1556	0.026*
C16	0.24913 (15)	0.32926 (16)	0.11149 (5)	0.0208 (3)
H16A	0.2235	0.2855	0.1361	0.025*
C17	−0.05057 (16)	0.33197 (16)	0.06350 (6)	0.0258 (3)
H17A	−0.1306	0.2851	0.0550	0.039*
H17B	−0.0586	0.4165	0.0459	0.039*
H17C	−0.0254	0.3504	0.0978	0.039*
C18	0.51856 (15)	0.56133 (16)	0.09975 (6)	0.0228 (3)
H18A	0.5288	0.6009	0.1317	0.027*
H18B	0.5065	0.6360	0.0766	0.027*
C19	0.64115 (15)	0.48568 (15)	0.09976 (5)	0.0193 (3)
H19A	0.6274	0.4395	0.0683	0.023*
C20	0.74986 (16)	0.58645 (16)	0.10501 (6)	0.0262 (3)
H20A	0.7281	0.6517	0.0790	0.039*
H20B	0.8250	0.5380	0.1038	0.039*
H20C	0.7650	0.6332	0.1356	0.039*
C21	0.67544 (15)	0.37717 (16)	0.13955 (6)	0.0227 (3)
H21A	0.7493	0.3281	0.1371	0.034*
H21B	0.6059	0.3147	0.1357	0.034*
H21C	0.6927	0.4204	0.1708	0.034*
C22	0.02950 (16)	−0.12061 (16)	0.16644 (5)	0.0224 (3)
H22A	−0.0588	−0.1475	0.1593	0.027*
H22B	0.0808	−0.2026	0.1740	0.027*
C23	0.18209 (15)	0.02413 (15)	0.22580 (5)	0.0196 (3)
C24	0.29008 (16)	−0.04544 (17)	0.22172 (6)	0.0227 (3)
H24A	0.2821	−0.1297	0.2061	0.027*
C25	0.40981 (16)	0.01206 (17)	0.24111 (6)	0.0258 (3)
H25A	0.4816	−0.0355	0.2391	0.031*
C26	0.42321 (16)	0.13885 (18)	0.26334 (6)	0.0275 (4)
H26A	0.5032	0.1768	0.2761	0.033*
C27	0.31547 (17)	0.20828 (17)	0.26626 (6)	0.0275 (4)
H27A	0.3236	0.2940	0.2808	0.033*
C28	0.19685 (15)	0.15264 (16)	0.24802 (6)	0.0231 (3)
H28A	0.1258	0.2009	0.2505	0.028*
C29	−0.03703 (14)	0.00563 (15)	0.22995 (5)	0.0183 (3)
C30	−0.14889 (15)	0.06584 (17)	0.20375 (6)	0.0234 (3)
H30A	−0.1623	0.0840	0.1708	0.028*
C31	−0.24132 (15)	0.09931 (17)	0.22671 (6)	0.0252 (3)
H31A	−0.3170	0.1389	0.2090	0.030*
C32	−0.22099 (15)	0.07391 (16)	0.27591 (6)	0.0238 (3)
H32A	−0.2830	0.0962	0.2912	0.029*
C33	−0.10801 (15)	0.01518 (15)	0.30232 (6)	0.0222 (3)
H33A	−0.0938	−0.0006	0.3354	0.027*
C34	−0.01663 (15)	−0.01996 (15)	0.27969 (6)	0.0207 (3)
H34A	0.0585	−0.0606	0.2974	0.025*

	U11	U22	U33	U12	U13	U23
Br1	0.02348 (8)	0.03478 (9)	0.01983 (7)	0.00250 (7)	0.00969 (6)	0.00190 (7)
S1	0.0432 (3)	0.01778 (18)	0.0276 (2)	0.00609 (17)	0.01949 (19)	0.00226 (15)
N1	0.0210 (6)	0.0184 (6)	0.0148 (5)	0.0036 (5)	0.0069 (5)	0.0005 (5)
N2	0.0205 (6)	0.0183 (6)	0.0200 (6)	0.0040 (5)	0.0064 (5)	0.0002 (5)
N3	0.0237 (6)	0.0183 (6)	0.0171 (6)	0.0025 (5)	0.0079 (5)	0.0003 (5)
N4	0.0200 (6)	0.0272 (7)	0.0181 (6)	−0.0008 (5)	0.0076 (5)	−0.0047 (5)
N5	0.0207 (6)	0.0199 (6)	0.0161 (5)	−0.0001 (5)	0.0066 (5)	−0.0017 (5)
C1	0.0221 (7)	0.0199 (7)	0.0168 (7)	0.0015 (6)	0.0067 (6)	−0.0008 (5)
C2	0.0165 (7)	0.0195 (7)	0.0168 (6)	0.0023 (5)	0.0044 (6)	−0.0018 (5)
C3	0.0225 (7)	0.0192 (7)	0.0156 (6)	0.0008 (6)	0.0052 (6)	0.0002 (5)
C4	0.0188 (7)	0.0173 (7)	0.0144 (6)	−0.0004 (5)	0.0037 (5)	−0.0014 (5)
C5	0.0251 (8)	0.0165 (7)	0.0160 (6)	0.0018 (6)	0.0053 (6)	−0.0006 (5)
C6	0.0208 (7)	0.0178 (7)	0.0193 (7)	0.0025 (6)	0.0051 (6)	−0.0032 (5)
C7	0.0209 (7)	0.0231 (7)	0.0146 (6)	−0.0007 (6)	0.0056 (6)	−0.0030 (5)
C8	0.0215 (7)	0.0212 (7)	0.0170 (7)	0.0027 (6)	0.0037 (6)	0.0018 (6)
C9	0.0197 (7)	0.0206 (7)	0.0175 (7)	0.0033 (6)	0.0040 (6)	−0.0008 (5)
C10	0.0209 (7)	0.0191 (7)	0.0178 (7)	0.0040 (6)	0.0036 (6)	0.0001 (5)
C11	0.0206 (7)	0.0151 (6)	0.0191 (7)	0.0051 (5)	0.0062 (6)	0.0004 (5)
C12	0.0242 (7)	0.0200 (7)	0.0151 (6)	0.0052 (6)	0.0028 (6)	0.0019 (5)
C13	0.0256 (8)	0.0210 (7)	0.0200 (7)	0.0043 (6)	0.0075 (6)	0.0048 (6)
C14	0.0222 (7)	0.0162 (7)	0.0212 (7)	0.0043 (5)	0.0061 (6)	0.0011 (5)
C15	0.0239 (8)	0.0240 (8)	0.0172 (7)	0.0031 (6)	0.0052 (6)	−0.0019 (6)
C16	0.0245 (8)	0.0220 (7)	0.0175 (7)	0.0024 (6)	0.0088 (6)	0.0013 (6)
C17	0.0220 (8)	0.0230 (8)	0.0317 (9)	0.0060 (6)	0.0059 (7)	0.0004 (7)
C18	0.0265 (8)	0.0180 (7)	0.0239 (8)	0.0008 (6)	0.0068 (6)	0.0011 (6)
C19	0.0242 (7)	0.0185 (7)	0.0163 (6)	−0.0004 (6)	0.0074 (6)	−0.0008 (5)
C20	0.0297 (9)	0.0208 (8)	0.0320 (9)	0.0001 (7)	0.0151 (7)	0.0009 (7)
C21	0.0251 (8)	0.0213 (7)	0.0213 (7)	0.0005 (6)	0.0059 (6)	0.0012 (6)
C22	0.0266 (8)	0.0234 (8)	0.0191 (7)	−0.0006 (6)	0.0099 (6)	−0.0016 (6)
C23	0.0218 (7)	0.0220 (8)	0.0164 (6)	0.0015 (6)	0.0074 (6)	0.0027 (5)
C24	0.0265 (8)	0.0241 (7)	0.0201 (7)	0.0031 (6)	0.0108 (6)	0.0007 (6)
C25	0.0218 (7)	0.0350 (9)	0.0231 (7)	0.0051 (7)	0.0106 (6)	0.0053 (7)
C26	0.0216 (8)	0.0352 (9)	0.0270 (8)	−0.0035 (7)	0.0088 (7)	0.0029 (7)
C27	0.0297 (9)	0.0237 (8)	0.0301 (9)	−0.0030 (7)	0.0101 (7)	0.0006 (7)
C28	0.0218 (7)	0.0215 (8)	0.0278 (8)	0.0019 (6)	0.0102 (7)	0.0033 (6)
C29	0.0196 (6)	0.0181 (7)	0.0179 (6)	0.0001 (6)	0.0062 (5)	−0.0011 (6)
C30	0.0260 (8)	0.0258 (8)	0.0171 (7)	0.0016 (7)	0.0038 (6)	0.0019 (6)
C31	0.0194 (7)	0.0266 (8)	0.0280 (8)	0.0029 (6)	0.0035 (6)	0.0025 (7)
C32	0.0200 (7)	0.0243 (8)	0.0299 (8)	0.0005 (6)	0.0116 (6)	−0.0030 (7)
C33	0.0254 (8)	0.0246 (8)	0.0182 (7)	−0.0008 (6)	0.0087 (6)	0.0004 (6)
C34	0.0203 (7)	0.0231 (8)	0.0180 (7)	0.0030 (6)	0.0042 (6)	0.0020 (6)

Br1—C7	1.8925 (16)	C17—H17A	0.96
S1—C1	1.6688 (15)	C17—H17B	0.96
N1—C2	1.3800 (19)	C17—H17C	0.96
N1—N5	1.3879 (18)	C18—C19	1.535 (2)
N1—C1	1.3907 (19)	C18—H18A	0.97
N2—C2	1.2968 (19)	C18—H18B	0.97
N2—N3	1.3818 (18)	C19—C20	1.522 (2)
N3—C1	1.354 (2)	C19—C21	1.526 (2)
N3—C22	1.466 (2)	C19—H19A	0.98
N4—C23	1.404 (2)	C20—H20A	0.96
N4—C29	1.422 (2)	C20—H20B	0.96
N4—C22	1.4399 (19)	C20—H20C	0.96
N5—C3	1.2821 (19)	C21—H21A	0.96
C2—C10	1.497 (2)	C21—H21B	0.96
C3—C4	1.456 (2)	C21—H21C	0.96
C3—H3A	0.93	C22—H22A	0.97
C4—C5	1.395 (2)	C22—H22B	0.97
C4—C9	1.408 (2)	C23—C28	1.398 (2)
C5—C6	1.383 (2)	C23—C24	1.398 (2)
C5—H5A	0.93	C24—C25	1.396 (2)
C6—C7	1.384 (2)	C24—H24A	0.93
C6—H6A	0.93	C25—C26	1.383 (2)
C7—C8	1.388 (2)	C25—H25A	0.93
C8—C9	1.378 (2)	C26—C27	1.385 (2)
C8—H8A	0.93	C26—H26A	0.93
C9—H9A	0.93	C27—C28	1.374 (2)
C10—C11	1.519 (2)	C27—H27A	0.93
C10—C17	1.531 (2)	C28—H28A	0.93
C10—H10A	0.98	C29—C30	1.381 (2)
C11—C12	1.392 (2)	C29—C34	1.402 (2)
C11—C16	1.392 (2)	C30—C31	1.390 (2)
C12—C13	1.386 (2)	C30—H30A	0.93
C12—H12A	0.93	C31—C32	1.386 (2)
C13—C14	1.397 (2)	C31—H31A	0.93
C13—H13A	0.93	C32—C33	1.386 (2)
C14—C15	1.395 (2)	C32—H32A	0.93
C14—C18	1.508 (2)	C33—C34	1.378 (2)
C15—C16	1.387 (2)	C33—H33A	0.93
C15—H15A	0.93	C34—H34A	0.93
C16—H16A	0.93
C2—N1—N5	118.83 (12)	H17B—C17—H17C	109.5
C2—N1—C1	108.47 (13)	C14—C18—C19	114.99 (13)
N5—N1—C1	132.69 (12)	C14—C18—H18A	108.5
C2—N2—N3	104.23 (12)	C19—C18—H18A	108.5
C1—N3—N2	113.84 (12)	C14—C18—H18B	108.5
C1—N3—C22	125.69 (13)	C19—C18—H18B	108.5
N2—N3—C22	120.35 (12)	H18A—C18—H18B	107.5
C23—N4—C29	119.80 (12)	C20—C19—C21	110.56 (13)
C23—N4—C22	121.01 (13)	C20—C19—C18	110.48 (12)
C29—N4—C22	119.14 (13)	C21—C19—C18	111.82 (13)
C3—N5—N1	118.00 (12)	C20—C19—H19A	107.9
N3—C1—N1	102.21 (12)	C21—C19—H19A	107.9
N3—C1—S1	127.43 (12)	C18—C19—H19A	107.9
N1—C1—S1	130.26 (12)	C19—C20—H20A	109.5
N2—C2—N1	111.21 (13)	C19—C20—H20B	109.5
N2—C2—C10	125.62 (13)	H20A—C20—H20B	109.5
N1—C2—C10	123.10 (13)	C19—C20—H20C	109.5
N5—C3—C4	119.71 (13)	H20A—C20—H20C	109.5
N5—C3—H3A	120.1	H20B—C20—H20C	109.5
C4—C3—H3A	120.1	C19—C21—H21A	109.5
C5—C4—C9	118.73 (14)	C19—C21—H21B	109.5
C5—C4—C3	118.76 (13)	H21A—C21—H21B	109.5
C9—C4—C3	122.39 (14)	C19—C21—H21C	109.5
C6—C5—C4	121.49 (14)	H21A—C21—H21C	109.5
C6—C5—H5A	119.3	H21B—C21—H21C	109.5
C4—C5—H5A	119.3	N4—C22—N3	112.04 (13)
C5—C6—C7	118.48 (14)	N4—C22—H22A	109.2
C5—C6—H6A	120.8	N3—C22—H22A	109.2
C7—C6—H6A	120.8	N4—C22—H22B	109.2
C6—C7—C8	121.48 (15)	N3—C22—H22B	109.2
C6—C7—Br1	119.31 (12)	H22A—C22—H22B	107.9
C8—C7—Br1	119.20 (12)	C28—C23—C24	118.75 (15)
C9—C8—C7	119.73 (14)	C28—C23—N4	119.42 (14)
C9—C8—H8A	120.1	C24—C23—N4	121.83 (14)
C7—C8—H8A	120.1	C25—C24—C23	119.77 (15)
C8—C9—C4	120.05 (14)	C25—C24—H24A	120.1
C8—C9—H9A	120.0	C23—C24—H24A	120.1
C4—C9—H9A	120.0	C26—C25—C24	120.90 (16)
C2—C10—C11	111.34 (12)	C26—C25—H25A	119.5
C2—C10—C17	110.33 (13)	C24—C25—H25A	119.5
C11—C10—C17	110.39 (12)	C25—C26—C27	118.88 (16)
C2—C10—H10A	108.2	C25—C26—H26A	120.6
C11—C10—H10A	108.2	C27—C26—H26A	120.6
C17—C10—H10A	108.2	C28—C27—C26	121.13 (16)
C12—C11—C16	118.23 (14)	C28—C27—H27A	119.4
C12—C11—C10	120.12 (13)	C26—C27—H27A	119.4
C16—C11—C10	121.44 (14)	C27—C28—C23	120.54 (15)
C13—C12—C11	120.94 (14)	C27—C28—H28A	119.7
C13—C12—H12A	119.5	C23—C28—H28A	119.7
C11—C12—H12A	119.5	C30—C29—C34	119.83 (14)
C12—C13—C14	121.13 (15)	C30—C29—N4	121.92 (14)
C12—C13—H13A	119.4	C34—C29—N4	118.25 (13)
C14—C13—H13A	119.4	C29—C30—C31	119.85 (14)
C15—C14—C13	117.60 (15)	C29—C30—H30A	120.1
C15—C14—C18	121.65 (14)	C31—C30—H30A	120.1
C13—C14—C18	120.75 (14)	C32—C31—C30	120.24 (15)
C16—C15—C14	121.29 (14)	C32—C31—H31A	119.9
C16—C15—H15A	119.4	C30—C31—H31A	119.9
C14—C15—H15A	119.4	C31—C32—C33	119.87 (15)
C15—C16—C11	120.77 (15)	C31—C32—H32A	120.1
C15—C16—H16A	119.6	C33—C32—H32A	120.1
C11—C16—H16A	119.6	C34—C33—C32	120.24 (15)
C10—C17—H17A	109.5	C34—C33—H33A	119.9
C10—C17—H17B	109.5	C32—C33—H33A	119.9
H17A—C17—H17B	109.5	C33—C34—C29	119.96 (14)
C10—C17—H17C	109.5	C33—C34—H34A	120.0
H17A—C17—H17C	109.5	C29—C34—H34A	120.0
C2—N2—N3—C1	−0.72 (16)	C11—C12—C13—C14	−0.1 (2)
C2—N2—N3—C22	175.64 (13)	C12—C13—C14—C15	1.3 (2)
C2—N1—N5—C3	159.63 (14)	C12—C13—C14—C18	−178.97 (14)
C1—N1—N5—C3	−21.9 (2)	C13—C14—C15—C16	−1.0 (2)
N2—N3—C1—N1	1.58 (16)	C18—C14—C15—C16	179.34 (14)
C22—N3—C1—N1	−174.54 (13)	C14—C15—C16—C11	−0.6 (2)
N2—N3—C1—S1	−175.19 (11)	C12—C11—C16—C15	1.8 (2)
C22—N3—C1—S1	8.7 (2)	C10—C11—C16—C15	−173.02 (14)
C2—N1—C1—N3	−1.81 (15)	C15—C14—C18—C19	91.60 (18)
N5—N1—C1—N3	179.61 (14)	C13—C14—C18—C19	−88.07 (18)
C2—N1—C1—S1	174.83 (12)	C14—C18—C19—C20	171.34 (13)
N5—N1—C1—S1	−3.7 (3)	C14—C18—C19—C21	−65.06 (17)
N3—N2—C2—N1	−0.53 (15)	C23—N4—C22—N3	−58.20 (18)
N3—N2—C2—C10	−177.61 (13)	C29—N4—C22—N3	119.16 (15)
N5—N1—C2—N2	−179.65 (12)	C1—N3—C22—N4	134.71 (15)
C1—N1—C2—N2	1.54 (17)	N2—N3—C22—N4	−41.18 (18)
N5—N1—C2—C10	−2.5 (2)	C29—N4—C23—C28	−28.3 (2)
C1—N1—C2—C10	178.71 (13)	C22—N4—C23—C28	149.07 (15)
N1—N5—C3—C4	−175.35 (12)	C29—N4—C23—C24	152.09 (15)
N5—C3—C4—C5	173.71 (14)	C22—N4—C23—C24	−30.6 (2)
N5—C3—C4—C9	−2.3 (2)	C28—C23—C24—C25	2.1 (2)
C9—C4—C5—C6	2.0 (2)	N4—C23—C24—C25	−178.29 (14)
C3—C4—C5—C6	−174.15 (14)	C23—C24—C25—C26	−1.6 (2)
C4—C5—C6—C7	−1.0 (2)	C24—C25—C26—C27	0.2 (2)
C5—C6—C7—C8	−0.5 (2)	C25—C26—C27—C28	0.7 (3)
C5—C6—C7—Br1	178.70 (11)	C26—C27—C28—C23	−0.2 (3)
C6—C7—C8—C9	1.0 (2)	C24—C23—C28—C27	−1.2 (2)
Br1—C7—C8—C9	−178.16 (11)	N4—C23—C28—C27	179.18 (15)
C7—C8—C9—C4	−0.1 (2)	C23—N4—C29—C30	121.59 (16)
C5—C4—C9—C8	−1.4 (2)	C22—N4—C29—C30	−55.8 (2)
C3—C4—C9—C8	174.57 (14)	C23—N4—C29—C34	−58.07 (19)
N2—C2—C10—C11	103.74 (17)	C22—N4—C29—C34	124.55 (15)
N1—C2—C10—C11	−73.02 (18)	C34—C29—C30—C31	−0.7 (2)
N2—C2—C10—C17	−19.2 (2)	N4—C29—C30—C31	179.60 (14)
N1—C2—C10—C17	164.05 (13)	C29—C30—C31—C32	0.7 (2)
C2—C10—C11—C12	135.56 (14)	C30—C31—C32—C33	0.1 (2)
C17—C10—C11—C12	−101.54 (16)	C31—C32—C33—C34	−1.0 (2)
C2—C10—C11—C16	−49.71 (19)	C32—C33—C34—C29	1.0 (2)
C17—C10—C11—C16	73.20 (17)	C30—C29—C34—C33	−0.1 (2)
C16—C11—C12—C13	−1.5 (2)	N4—C29—C34—C33	179.55 (14)
C10—C11—C12—C13	173.45 (14)

D—H···A	D—H	H···A	D···A	D—H···A
C3—H3A···S1	0.93	2.52	3.217 (2)	132
C22—H22B···S1	0.97	2.80	3.232 (2)	108
C6—H6A···Cg1i	0.93	2.81	3.717 (2)	165
C21—H21C···Cg2ii	0.96	2.89	3.829 (2)	168

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C3—H3A⋯S1	0.93	2.52	3.217 (2)	132
C22—H22B⋯S1	0.97	2.80	3.232 (2)	108
C6—H6A⋯Cg1i	0.93	2.81	3.717 (2)	165
C21—H21C⋯Cg2ii	0.96	2.89	3.829 (2)	168

Symmetry codes: (i) ; (ii) . Cg1 and Cg2 are the centroids of the C11–C16 and C23–C28 rings, respectively.