4-(4-Bromo-benzyl-ideneamino)-3-{1-[4-(2-methyl-prop-yl)phen-yl]eth-yl}-1-(mor-phol-ino-meth-yl)-1H-1,2,4-triazole-5(4H)-thione.

There are two mol-ecules (A and B) in the asymmetric unit of the title compound, C(26)H(32)BrN(5)OS, with almost identical geometry. The morpholine ring adopts the usual chair conformation in both mol-ecules. The triazole ring forms dihedral angles of 4.84 (6) and 74.19 (6)°, respectively, with the bromo-phenyl and isobutylbenzene rings in mol-ecule A, and angles of 16.68 (7) and 87.29 (6)°, respectively, in mol-ecule B. Intra-molecular C-H⋯S hydrogen bonds generate S(5) and S(6) ring motifs in both independent mol-ecules. The crystal structure is stabilized by C-H⋯N, C-H⋯Br and C-H⋯O hydrogen-bonding inter-actions, together with C-H⋯π inter-actions.

Related literature

For general background, see: Raman et al. (2004 ▶); Tramontini et al. (1988 ▶); Tramontini & Angliolini (1990 ▶); Lopes et al. (2004 ▶); Joshi et al. (2004 ▶); Ferlin et al. (2002 ▶); Holla et al. (2003 ▶); Malinka et al. (2005 ▶); Karthikeyan et al. (2006 ▶); Palaska et al. (2002 ▶). For related structures, see: Fun, Jebas, Razak et al. (2008 ▶); Fun, Jebas, Sujith et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶). For ring puckering analysis, see: Cremer & Pople (1975 ▶). For graph-set analysis of hydrogen bonding, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C26H32BrN5OS

M = 542.54

Triclinic,

a = 10.1381 (1) Å

b = 17.0356 (2) Å

c = 17.2077 (2) Å

α = 64.168 (1)°

β = 79.773 (1)°

γ = 78.816 (1)°

V = 2609.55 (6) Å3

Z = 4

Mo Kα radiation

μ = 1.68 mm−1

T = 100.0 (1) K

0.45 × 0.34 × 0.26 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.522, T max = 0.639

89536 measured reflections

18804 independent reflections

13217 reflections with I > 2σ(I)

R int = 0.044

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.097

S = 1.02

18804 reflections

619 parameters

H-atom parameters constrained

Δρmax = 1.33 e Å−3

Δρmin = −0.84 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/S160053680802254X/ci2634sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680802254X/ci2634Isup2.hkl

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

C26H32BrN5OS	Z = 4
Mr = 542.54	F000 = 1128
Triclinic, P1	Dx = 1.381 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 10.1381 (1) Å	Cell parameters from 9909 reflections
b = 17.0356 (2) Å	θ = 2.2–29.6º
c = 17.2077 (2) Å	µ = 1.68 mm−1
α = 64.168 (1)º	T = 100.0 (1) K
β = 79.773 (1)º	Block, colourless
γ = 78.816 (1)º	0.45 × 0.34 × 0.26 mm
V = 2609.55 (6) Å3

Bruker SMART APEXII CCD area-detector diffractometer	18804 independent reflections
Radiation source: fine-focus sealed tube	13217 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.044
T = 100.0(1) K	θmax = 32.5º
φ and ω scans	θmin = 1.3º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −15→14
Tmin = 0.523, Tmax = 0.639	k = −25→25
89536 measured reflections	l = −26→25

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)] = 0.039	H-atom parameters constrained
wR(F2) = 0.097	w = 1/[σ2(Fo2) + (0.038P)2 + 1.3091P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max = 0.001
18804 reflections	Δρmax = 1.33 e Å−3
619 parameters	Δρmin = −0.84 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
Br1A	1.463972 (19)	−0.136890 (12)	−0.024526 (12)	0.02730 (5)
S1A	0.72929 (5)	0.25031 (3)	−0.21857 (3)	0.02396 (9)
O1A	0.19942 (14)	0.30933 (10)	−0.05409 (9)	0.0338 (3)
N1A	0.94677 (15)	0.20300 (9)	−0.06764 (9)	0.0216 (3)
N2A	0.83105 (14)	0.26411 (9)	−0.08571 (9)	0.0195 (3)
N3A	0.65694 (15)	0.35672 (9)	−0.13441 (9)	0.0201 (3)
N4A	0.69613 (15)	0.37728 (9)	−0.07311 (9)	0.0217 (3)
N5A	0.41603 (15)	0.40103 (9)	−0.15946 (9)	0.0220 (3)
C1A	1.18024 (19)	0.07350 (12)	−0.02429 (11)	0.0256 (4)
H1AA	1.1651	0.1122	0.0023	0.031*
C2A	1.29078 (19)	0.00937 (13)	−0.00761 (11)	0.0266 (4)
H2AA	1.3498	0.0041	0.0306	0.032*
C3A	1.31323 (18)	−0.04743 (11)	−0.04847 (11)	0.0216 (3)
C4A	1.22709 (19)	−0.04131 (11)	−0.10530 (11)	0.0231 (3)
H4AA	1.2435	−0.0796	−0.1324	0.028*
C5A	1.11568 (18)	0.02303 (11)	−0.12113 (11)	0.0235 (3)
H5AA	1.0567	0.0277	−0.1591	0.028*
C6A	1.09067 (18)	0.08075 (11)	−0.08100 (11)	0.0210 (3)
C7A	0.96930 (18)	0.14595 (11)	−0.09930 (11)	0.0231 (3)
H7AA	0.9088	0.1457	−0.1340	0.028*
C8A	0.73866 (17)	0.28902 (11)	−0.14594 (10)	0.0196 (3)
C9A	0.55336 (18)	0.41834 (11)	−0.18951 (11)	0.0231 (3)
H9AA	0.5592	0.4770	−0.1958	0.028*
H9AB	0.5749	0.4184	−0.2468	0.028*
C10A	0.38410 (18)	0.32459 (11)	−0.16766 (11)	0.0229 (3)
H10A	0.4380	0.2717	−0.1314	0.028*
H10B	0.4062	0.3317	−0.2274	0.028*
C11A	0.23609 (19)	0.31572 (13)	−0.14053 (12)	0.0281 (4)
H11A	0.1826	0.3664	−0.1801	0.034*
H11B	0.2168	0.2636	−0.1436	0.034*
C12A	0.2238 (2)	0.38716 (15)	−0.05031 (14)	0.0332 (4)
H12A	0.1942	0.3845	0.0075	0.040*
H12B	0.1723	0.4380	−0.0911	0.040*
C13A	0.37267 (19)	0.39652 (13)	−0.07209 (12)	0.0268 (4)
H13A	0.3886	0.4495	−0.0693	0.032*
H13B	0.4242	0.3466	−0.0304	0.032*
C14A	0.80121 (18)	0.32077 (11)	−0.04479 (11)	0.0207 (3)
C15A	0.88283 (18)	0.31567 (11)	0.02201 (11)	0.0221 (3)
H15A	0.9783	0.3022	0.0034	0.027*
C16A	0.84828 (17)	0.24255 (11)	0.11050 (11)	0.0210 (3)
C17A	0.94838 (18)	0.17541 (13)	0.15147 (12)	0.0248 (4)
H17A	1.0356	0.1739	0.1235	0.030*
C18A	0.91887 (19)	0.11064 (13)	0.23385 (12)	0.0263 (4)
H18A	0.9871	0.0663	0.2602	0.032*
C19A	0.79030 (19)	0.11052 (12)	0.27771 (11)	0.0240 (3)
C20A	0.68960 (18)	0.17745 (12)	0.23622 (11)	0.0235 (3)
H20A	0.6024	0.1788	0.2642	0.028*
C21A	0.71812 (18)	0.24208 (12)	0.15355 (12)	0.0231 (3)
H21A	0.6494	0.2856	0.1266	0.028*
C22A	0.7604 (2)	0.04019 (13)	0.36753 (12)	0.0316 (4)
H22A	0.7927	−0.0169	0.3667	0.038*
H22B	0.6632	0.0437	0.3823	0.038*
C23A	0.8239 (2)	0.04639 (17)	0.43828 (13)	0.0390 (5)
H23A	0.9221	0.0418	0.4230	0.047*
C24A	0.7948 (3)	−0.0314 (2)	0.52512 (14)	0.0553 (7)
H24A	0.8314	−0.0258	0.5699	0.083*
H24B	0.8358	−0.0854	0.5209	0.083*
H24C	0.6989	−0.0319	0.5389	0.083*
C25A	0.7781 (3)	0.13307 (19)	0.44434 (17)	0.0565 (7)
H25A	0.8002	0.1801	0.3893	0.085*
H25B	0.8226	0.1353	0.4880	0.085*
H25C	0.6820	0.1392	0.4596	0.085*
C26A	0.8647 (2)	0.40454 (12)	0.02743 (13)	0.0291 (4)
H26A	0.8920	0.4488	−0.0283	0.044*
H26B	0.9192	0.4006	0.0696	0.044*
H26C	0.7714	0.4200	0.0444	0.044*
Br1B	0.48478 (3)	0.645886 (13)	0.647264 (13)	0.03762 (6)
S1B	0.08036 (5)	0.55979 (3)	0.28269 (3)	0.02256 (9)
O1B	0.35396 (15)	0.25009 (11)	0.22342 (11)	0.0440 (4)
N1B	0.13059 (14)	0.44610 (9)	0.49490 (9)	0.0176 (3)
N2B	0.07466 (14)	0.41862 (9)	0.44400 (8)	0.0166 (3)
N3B	0.00212 (14)	0.39715 (9)	0.34664 (8)	0.0180 (3)
N4B	−0.01975 (14)	0.32382 (9)	0.42336 (9)	0.0190 (3)
N5B	0.09910 (15)	0.35433 (10)	0.22751 (9)	0.0219 (3)
C1B	0.36569 (18)	0.59648 (11)	0.45716 (11)	0.0233 (3)
H1BA	0.3785	0.6186	0.3969	0.028*
C2B	0.42654 (19)	0.63059 (11)	0.49939 (11)	0.0256 (4)
H2BA	0.4802	0.6753	0.4681	0.031*
C3B	0.40603 (18)	0.59695 (11)	0.58892 (11)	0.0227 (3)
C4B	0.32932 (17)	0.52864 (11)	0.63734 (11)	0.0212 (3)
H4BA	0.3185	0.5060	0.6976	0.025*
C5B	0.26936 (17)	0.49485 (11)	0.59445 (10)	0.0192 (3)
H5BA	0.2181	0.4489	0.6261	0.023*
C6B	0.28537 (17)	0.52939 (11)	0.50386 (10)	0.0183 (3)
C7B	0.22076 (17)	0.49746 (11)	0.45565 (11)	0.0200 (3)
H7BA	0.2453	0.5145	0.3964	0.024*
C8B	0.05586 (16)	0.45842 (11)	0.35662 (10)	0.0178 (3)
C9B	−0.01500 (17)	0.39801 (11)	0.26330 (10)	0.0206 (3)
H9BA	−0.0941	0.3701	0.2710	0.025*
H9BB	−0.0323	0.4587	0.2217	0.025*
C10B	0.1158 (2)	0.25835 (12)	0.27558 (13)	0.0304 (4)
H10C	0.0330	0.2359	0.2791	0.036*
H10D	0.1354	0.2424	0.3342	0.036*
C11B	0.2306 (2)	0.21881 (15)	0.22926 (16)	0.0406 (5)
H11C	0.2414	0.1552	0.2603	0.049*
H11D	0.2092	0.2337	0.1713	0.049*
C12B	0.3396 (2)	0.34296 (16)	0.17616 (14)	0.0368 (5)
H12C	0.3220	0.3580	0.1174	0.044*
H12D	0.4235	0.3641	0.1729	0.044*
C13B	0.22578 (18)	0.38805 (13)	0.21804 (12)	0.0258 (4)
H13C	0.2472	0.3780	0.2747	0.031*
H13D	0.2157	0.4510	0.1826	0.031*
C14B	0.02267 (16)	0.33944 (10)	0.48161 (10)	0.0172 (3)
C15B	0.01969 (17)	0.28116 (10)	0.57663 (10)	0.0182 (3)
H15B	−0.0241	0.3166	0.6085	0.022*
C16B	0.16129 (17)	0.24513 (10)	0.60310 (10)	0.0175 (3)
C17B	0.26067 (18)	0.21508 (11)	0.55173 (11)	0.0213 (3)
H17B	0.2406	0.2185	0.4996	0.026*
C18B	0.38945 (18)	0.18011 (11)	0.57731 (11)	0.0224 (3)
H18B	0.4543	0.1604	0.5419	0.027*
C19B	0.42331 (17)	0.17395 (10)	0.65474 (10)	0.0198 (3)
C20B	0.32294 (19)	0.20293 (11)	0.70662 (11)	0.0234 (3)
H20B	0.3426	0.1986	0.7592	0.028*
C21B	0.19414 (19)	0.23818 (11)	0.68119 (11)	0.0231 (3)
H21B	0.1290	0.2574	0.7168	0.028*
C22B	0.56389 (17)	0.13790 (11)	0.68160 (11)	0.0220 (3)
H22C	0.5943	0.1779	0.6990	0.026*
H22D	0.6242	0.1359	0.6318	0.026*
C23B	0.57477 (17)	0.04546 (11)	0.75647 (11)	0.0195 (3)
H23B	0.5192	0.0490	0.8079	0.023*
C24B	0.52154 (19)	−0.01900 (11)	0.73412 (12)	0.0254 (4)
H24D	0.5318	−0.0765	0.7808	0.038*
H24E	0.5716	−0.0208	0.6819	0.038*
H24F	0.4276	−0.0003	0.7255	0.038*
C25B	0.72130 (19)	0.01507 (12)	0.77739 (12)	0.0267 (4)
H25D	0.7277	−0.0423	0.8246	0.040*
H25E	0.7505	0.0558	0.7934	0.040*
H25F	0.7778	0.0126	0.7272	0.040*
C26B	−0.06443 (18)	0.20662 (11)	0.60044 (11)	0.0236 (3)
H26D	−0.1538	0.2312	0.5835	0.035*
H26E	−0.0698	0.1717	0.6620	0.035*
H26F	−0.0224	0.1703	0.5708	0.035*

	U11	U22	U33	U12	U13	U23
Br1A	0.02633 (10)	0.02249 (9)	0.02637 (9)	0.00006 (7)	−0.00519 (7)	−0.00446 (7)
S1A	0.0275 (2)	0.0264 (2)	0.0216 (2)	−0.00191 (17)	−0.00418 (16)	−0.01344 (17)
O1A	0.0275 (7)	0.0451 (8)	0.0330 (7)	−0.0110 (6)	0.0043 (6)	−0.0203 (6)
N1A	0.0193 (7)	0.0218 (7)	0.0243 (7)	−0.0027 (5)	−0.0016 (5)	−0.0103 (6)
N2A	0.0193 (7)	0.0206 (7)	0.0214 (7)	−0.0046 (5)	−0.0002 (5)	−0.0113 (5)
N3A	0.0212 (7)	0.0204 (7)	0.0199 (6)	−0.0037 (5)	−0.0009 (5)	−0.0095 (5)
N4A	0.0232 (7)	0.0220 (7)	0.0227 (7)	−0.0058 (6)	0.0005 (5)	−0.0118 (6)
N5A	0.0237 (8)	0.0210 (7)	0.0206 (7)	−0.0010 (6)	−0.0028 (5)	−0.0085 (6)
C1A	0.0271 (9)	0.0290 (9)	0.0259 (9)	−0.0028 (7)	−0.0024 (7)	−0.0167 (7)
C2A	0.0256 (9)	0.0331 (10)	0.0229 (8)	−0.0054 (7)	−0.0045 (7)	−0.0119 (7)
C3A	0.0225 (8)	0.0184 (8)	0.0200 (8)	−0.0031 (6)	−0.0016 (6)	−0.0043 (6)
C4A	0.0269 (9)	0.0192 (8)	0.0253 (8)	−0.0028 (7)	−0.0042 (7)	−0.0106 (7)
C5A	0.0246 (9)	0.0239 (8)	0.0257 (8)	−0.0029 (7)	−0.0062 (7)	−0.0125 (7)
C6A	0.0217 (8)	0.0195 (8)	0.0213 (8)	−0.0047 (6)	−0.0010 (6)	−0.0078 (6)
C7A	0.0227 (9)	0.0235 (8)	0.0257 (8)	−0.0050 (7)	−0.0029 (6)	−0.0118 (7)
C8A	0.0211 (8)	0.0194 (8)	0.0165 (7)	−0.0063 (6)	0.0006 (6)	−0.0054 (6)
C9A	0.0257 (9)	0.0179 (8)	0.0215 (8)	−0.0029 (7)	−0.0022 (6)	−0.0046 (6)
C10A	0.0240 (9)	0.0213 (8)	0.0219 (8)	−0.0004 (7)	−0.0042 (6)	−0.0078 (7)
C11A	0.0242 (9)	0.0336 (10)	0.0290 (9)	−0.0027 (7)	−0.0035 (7)	−0.0155 (8)
C12A	0.0237 (10)	0.0465 (12)	0.0350 (10)	0.0008 (8)	−0.0013 (8)	−0.0248 (9)
C13A	0.0241 (9)	0.0321 (10)	0.0273 (9)	0.0002 (7)	−0.0031 (7)	−0.0167 (8)
C14A	0.0224 (8)	0.0197 (8)	0.0222 (8)	−0.0066 (6)	0.0019 (6)	−0.0109 (6)
C15A	0.0184 (8)	0.0259 (9)	0.0276 (8)	−0.0038 (6)	−0.0013 (6)	−0.0162 (7)
C16A	0.0192 (8)	0.0252 (8)	0.0257 (8)	−0.0033 (6)	−0.0025 (6)	−0.0168 (7)
C17A	0.0154 (8)	0.0361 (10)	0.0315 (9)	0.0002 (7)	−0.0041 (7)	−0.0228 (8)
C18A	0.0234 (9)	0.0312 (10)	0.0300 (9)	0.0048 (7)	−0.0114 (7)	−0.0181 (8)
C19A	0.0266 (9)	0.0266 (9)	0.0248 (8)	−0.0023 (7)	−0.0067 (7)	−0.0153 (7)
C20A	0.0187 (8)	0.0290 (9)	0.0284 (9)	−0.0037 (7)	−0.0003 (6)	−0.0174 (7)
C21A	0.0189 (8)	0.0238 (8)	0.0293 (9)	0.0015 (6)	−0.0042 (6)	−0.0147 (7)
C22A	0.0373 (11)	0.0333 (10)	0.0267 (9)	−0.0062 (8)	−0.0083 (8)	−0.0123 (8)
C23A	0.0300 (11)	0.0637 (15)	0.0280 (10)	−0.0085 (10)	−0.0037 (8)	−0.0222 (10)
C24A	0.0545 (16)	0.080 (2)	0.0273 (11)	−0.0111 (14)	−0.0072 (10)	−0.0161 (12)
C25A	0.0701 (19)	0.0764 (19)	0.0456 (14)	−0.0289 (15)	0.0060 (12)	−0.0427 (14)
C26A	0.0287 (10)	0.0284 (9)	0.0376 (10)	−0.0061 (8)	−0.0023 (8)	−0.0198 (8)
Br1B	0.06026 (15)	0.02600 (10)	0.03119 (10)	−0.01396 (9)	−0.02188 (9)	−0.00635 (8)
S1B	0.0235 (2)	0.01844 (19)	0.02141 (19)	−0.00316 (16)	−0.00178 (15)	−0.00441 (15)
O1B	0.0279 (8)	0.0540 (10)	0.0624 (10)	0.0112 (7)	−0.0086 (7)	−0.0409 (9)
N1B	0.0166 (7)	0.0163 (6)	0.0215 (6)	0.0002 (5)	−0.0045 (5)	−0.0092 (5)
N2B	0.0168 (7)	0.0155 (6)	0.0179 (6)	−0.0016 (5)	−0.0018 (5)	−0.0074 (5)
N3B	0.0181 (7)	0.0175 (6)	0.0179 (6)	−0.0006 (5)	−0.0027 (5)	−0.0072 (5)
N4B	0.0183 (7)	0.0177 (6)	0.0205 (6)	−0.0011 (5)	−0.0024 (5)	−0.0080 (5)
N5B	0.0194 (7)	0.0267 (7)	0.0236 (7)	−0.0007 (6)	−0.0032 (5)	−0.0146 (6)
C1B	0.0248 (9)	0.0233 (8)	0.0197 (8)	−0.0062 (7)	−0.0030 (6)	−0.0054 (7)
C2B	0.0301 (10)	0.0198 (8)	0.0249 (8)	−0.0090 (7)	−0.0077 (7)	−0.0033 (7)
C3B	0.0256 (9)	0.0190 (8)	0.0252 (8)	−0.0015 (6)	−0.0104 (7)	−0.0084 (7)
C4B	0.0212 (8)	0.0213 (8)	0.0195 (7)	0.0000 (6)	−0.0047 (6)	−0.0073 (6)
C5B	0.0178 (8)	0.0177 (7)	0.0201 (7)	−0.0008 (6)	−0.0018 (6)	−0.0067 (6)
C6B	0.0172 (8)	0.0178 (7)	0.0197 (7)	−0.0008 (6)	−0.0026 (6)	−0.0079 (6)
C7B	0.0187 (8)	0.0229 (8)	0.0199 (7)	−0.0025 (6)	−0.0010 (6)	−0.0109 (6)
C8B	0.0135 (7)	0.0193 (7)	0.0197 (7)	0.0011 (6)	−0.0014 (5)	−0.0087 (6)
C9B	0.0178 (8)	0.0261 (8)	0.0200 (7)	0.0006 (6)	−0.0062 (6)	−0.0113 (7)
C10B	0.0319 (10)	0.0268 (9)	0.0360 (10)	0.0005 (8)	−0.0028 (8)	−0.0184 (8)
C11B	0.0349 (12)	0.0411 (12)	0.0560 (14)	0.0033 (9)	−0.0026 (10)	−0.0337 (11)
C12B	0.0234 (10)	0.0574 (14)	0.0424 (11)	−0.0027 (9)	0.0007 (8)	−0.0352 (11)
C13B	0.0202 (9)	0.0329 (10)	0.0279 (9)	−0.0026 (7)	−0.0010 (7)	−0.0169 (8)
C14B	0.0148 (7)	0.0152 (7)	0.0209 (7)	0.0004 (6)	−0.0008 (6)	−0.0082 (6)
C15B	0.0177 (8)	0.0170 (7)	0.0187 (7)	−0.0021 (6)	0.0002 (6)	−0.0072 (6)
C16B	0.0192 (8)	0.0132 (7)	0.0185 (7)	−0.0023 (6)	−0.0020 (6)	−0.0051 (6)
C17B	0.0213 (8)	0.0234 (8)	0.0200 (8)	−0.0001 (6)	−0.0030 (6)	−0.0105 (6)
C18B	0.0186 (8)	0.0252 (9)	0.0221 (8)	−0.0008 (6)	0.0006 (6)	−0.0105 (7)
C19B	0.0215 (8)	0.0147 (7)	0.0209 (7)	−0.0050 (6)	−0.0029 (6)	−0.0039 (6)
C20B	0.0291 (9)	0.0222 (8)	0.0205 (8)	0.0006 (7)	−0.0071 (7)	−0.0103 (7)
C21B	0.0267 (9)	0.0228 (8)	0.0194 (8)	0.0005 (7)	−0.0009 (6)	−0.0106 (7)
C22B	0.0196 (8)	0.0206 (8)	0.0244 (8)	−0.0048 (6)	−0.0042 (6)	−0.0065 (7)
C23B	0.0172 (8)	0.0201 (8)	0.0205 (7)	−0.0007 (6)	−0.0036 (6)	−0.0080 (6)
C24B	0.0262 (9)	0.0206 (8)	0.0294 (9)	−0.0028 (7)	−0.0059 (7)	−0.0095 (7)
C25B	0.0225 (9)	0.0279 (9)	0.0289 (9)	0.0011 (7)	−0.0076 (7)	−0.0110 (7)
C26B	0.0227 (9)	0.0223 (8)	0.0248 (8)	−0.0063 (7)	−0.0001 (6)	−0.0083 (7)

Br1A—C3A	1.8975 (18)	Br1B—C3B	1.9007 (17)
S1A—C8A	1.6707 (17)	S1B—C8B	1.6740 (16)
O1A—C12A	1.425 (3)	O1B—C12B	1.420 (3)
O1A—C11A	1.429 (2)	O1B—C11B	1.423 (3)
N1A—C7A	1.275 (2)	N1B—C7B	1.278 (2)
N1A—N2A	1.389 (2)	N1B—N2B	1.3946 (18)
N2A—C14A	1.387 (2)	N2B—C14B	1.382 (2)
N2A—C8A	1.392 (2)	N2B—C8B	1.386 (2)
N3A—C8A	1.351 (2)	N3B—C8B	1.351 (2)
N3A—N4A	1.3850 (19)	N3B—N4B	1.3853 (18)
N3A—C9A	1.470 (2)	N3B—C9B	1.468 (2)
N4A—C14A	1.295 (2)	N4B—C14B	1.300 (2)
N5A—C9A	1.436 (2)	N5B—C9B	1.444 (2)
N5A—C13A	1.462 (2)	N5B—C13B	1.462 (2)
N5A—C10A	1.470 (2)	N5B—C10B	1.466 (2)
C1A—C2A	1.378 (3)	C1B—C2B	1.383 (2)
C1A—C6A	1.399 (2)	C1B—C6B	1.394 (2)
C1A—H1AA	0.93	C1B—H1BA	0.93
C2A—C3A	1.390 (3)	C2B—C3B	1.381 (2)
C2A—H2AA	0.93	C2B—H2BA	0.93
C3A—C4A	1.382 (2)	C3B—C4B	1.389 (2)
C4A—C5A	1.386 (3)	C4B—C5B	1.382 (2)
C4A—H4AA	0.93	C4B—H4BA	0.93
C5A—C6A	1.393 (2)	C5B—C6B	1.397 (2)
C5A—H5AA	0.93	C5B—H5BA	0.93
C6A—C7A	1.466 (2)	C6B—C7B	1.462 (2)
C7A—H7AA	0.93	C7B—H7BA	0.93
C9A—H9AA	0.97	C9B—H9BA	0.97
C9A—H9AB	0.97	C9B—H9BB	0.97
C10A—C11A	1.507 (3)	C10B—C11B	1.509 (3)
C10A—H10A	0.97	C10B—H10C	0.97
C10A—H10B	0.97	C10B—H10D	0.97
C11A—H11A	0.97	C11B—H11C	0.97
C11A—H11B	0.97	C11B—H11D	0.97
C12A—C13A	1.512 (3)	C12B—C13B	1.512 (3)
C12A—H12A	0.97	C12B—H12C	0.97
C12A—H12B	0.97	C12B—H12D	0.97
C13A—H13A	0.97	C13B—H13C	0.97
C13A—H13B	0.97	C13B—H13D	0.97
C14A—C15A	1.495 (2)	C14B—C15B	1.496 (2)
C15A—C16A	1.523 (2)	C15B—C16B	1.514 (2)
C15A—C26A	1.531 (2)	C15B—C26B	1.533 (2)
C15A—H15A	0.98	C15B—H15B	0.98
C16A—C17A	1.391 (2)	C16B—C21B	1.391 (2)
C16A—C21A	1.394 (2)	C16B—C17B	1.392 (2)
C17A—C18A	1.390 (3)	C17B—C18B	1.388 (2)
C17A—H17A	0.93	C17B—H17B	0.93
C18A—C19A	1.385 (3)	C18B—C19B	1.390 (2)
C18A—H18A	0.93	C18B—H18B	0.93
C19A—C20A	1.396 (3)	C19B—C20B	1.394 (2)
C19A—C22A	1.509 (3)	C19B—C22B	1.506 (2)
C20A—C21A	1.390 (3)	C20B—C21B	1.388 (3)
C20A—H20A	0.93	C20B—H20B	0.93
C21A—H21A	0.93	C21B—H21B	0.93
C22A—C23A	1.525 (3)	C22B—C23B	1.538 (2)
C22A—H22A	0.97	C22B—H22C	0.97
C22A—H22B	0.97	C22B—H22D	0.97
C23A—C25A	1.503 (4)	C23B—C24B	1.522 (2)
C23A—C24A	1.532 (3)	C23B—C25B	1.528 (2)
C23A—H23A	0.98	C23B—H23B	0.98
C24A—H24A	0.96	C24B—H24D	0.96
C24A—H24B	0.96	C24B—H24E	0.96
C24A—H24C	0.96	C24B—H24F	0.96
C25A—H25A	0.96	C25B—H25D	0.96
C25A—H25B	0.96	C25B—H25E	0.96
C25A—H25C	0.96	C25B—H25F	0.96
C26A—H26A	0.96	C26B—H26D	0.96
C26A—H26B	0.96	C26B—H26E	0.96
C26A—H26C	0.96	C26B—H26F	0.96
C12A—O1A—C11A	109.42 (15)	C12B—O1B—C11B	109.53 (16)
C7A—N1A—N2A	118.96 (15)	C7B—N1B—N2B	116.17 (13)
C14A—N2A—N1A	118.48 (14)	C14B—N2B—C8B	108.67 (13)
C14A—N2A—C8A	108.24 (14)	C14B—N2B—N1B	119.85 (13)
N1A—N2A—C8A	132.91 (14)	C8B—N2B—N1B	131.46 (13)
C8A—N3A—N4A	113.15 (14)	C8B—N3B—N4B	113.52 (13)
C8A—N3A—C9A	127.36 (14)	C8B—N3B—C9B	125.58 (14)
N4A—N3A—C9A	118.31 (14)	N4B—N3B—C9B	120.31 (13)
C14A—N4A—N3A	105.00 (13)	C14B—N4B—N3B	104.42 (13)
C9A—N5A—C13A	113.45 (14)	C9B—N5B—C13B	113.07 (14)
C9A—N5A—C10A	114.09 (14)	C9B—N5B—C10B	113.21 (14)
C13A—N5A—C10A	111.22 (14)	C13B—N5B—C10B	110.14 (15)
C2A—C1A—C6A	120.34 (16)	C2B—C1B—C6B	120.78 (16)
C2A—C1A—H1AA	119.8	C2B—C1B—H1BA	119.6
C6A—C1A—H1AA	119.8	C6B—C1B—H1BA	119.6
C1A—C2A—C3A	119.29 (17)	C3B—C2B—C1B	118.68 (16)
C1A—C2A—H2AA	120.4	C3B—C2B—H2BA	120.7
C3A—C2A—H2AA	120.4	C1B—C2B—H2BA	120.7
C4A—C3A—C2A	121.59 (17)	C2B—C3B—C4B	121.87 (16)
C4A—C3A—Br1A	118.94 (13)	C2B—C3B—Br1B	118.95 (13)
C2A—C3A—Br1A	119.46 (13)	C4B—C3B—Br1B	119.18 (13)
C3A—C4A—C5A	118.64 (16)	C5B—C4B—C3B	118.93 (15)
C3A—C4A—H4AA	120.7	C5B—C4B—H4BA	120.5
C5A—C4A—H4AA	120.7	C3B—C4B—H4BA	120.5
C4A—C5A—C6A	120.98 (16)	C4B—C5B—C6B	120.32 (15)
C4A—C5A—H5AA	119.5	C4B—C5B—H5BA	119.8
C6A—C5A—H5AA	119.5	C6B—C5B—H5BA	119.8
C5A—C6A—C1A	119.16 (16)	C1B—C6B—C5B	119.38 (15)
C5A—C6A—C7A	118.04 (15)	C1B—C6B—C7B	118.38 (15)
C1A—C6A—C7A	122.80 (16)	C5B—C6B—C7B	122.24 (15)
N1A—C7A—C6A	119.92 (16)	N1B—C7B—C6B	120.00 (15)
N1A—C7A—H7AA	120.0	N1B—C7B—H7BA	120.0
C6A—C7A—H7AA	120.0	C6B—C7B—H7BA	120.0
N3A—C8A—N2A	102.82 (14)	N3B—C8B—N2B	102.52 (13)
N3A—C8A—S1A	126.71 (13)	N3B—C8B—S1B	127.83 (12)
N2A—C8A—S1A	130.43 (13)	N2B—C8B—S1B	129.48 (12)
N5A—C9A—N3A	116.28 (14)	N5B—C9B—N3B	114.70 (13)
N5A—C9A—H9AA	108.2	N5B—C9B—H9BA	108.6
N3A—C9A—H9AA	108.2	N3B—C9B—H9BA	108.6
N5A—C9A—H9AB	108.2	N5B—C9B—H9BB	108.6
N3A—C9A—H9AB	108.2	N3B—C9B—H9BB	108.6
H9AA—C9A—H9AB	107.4	H9BA—C9B—H9BB	107.6
N5A—C10A—C11A	110.09 (15)	N5B—C10B—C11B	109.00 (17)
N5A—C10A—H10A	109.6	N5B—C10B—H10C	109.9
C11A—C10A—H10A	109.6	C11B—C10B—H10C	109.9
N5A—C10A—H10B	109.6	N5B—C10B—H10D	109.9
C11A—C10A—H10B	109.6	C11B—C10B—H10D	109.9
H10A—C10A—H10B	108.2	H10C—C10B—H10D	108.3
O1A—C11A—C10A	110.79 (15)	O1B—C11B—C10B	111.30 (17)
O1A—C11A—H11A	109.5	O1B—C11B—H11C	109.4
C10A—C11A—H11A	109.5	C10B—C11B—H11C	109.4
O1A—C11A—H11B	109.5	O1B—C11B—H11D	109.4
C10A—C11A—H11B	109.5	C10B—C11B—H11D	109.4
H11A—C11A—H11B	108.1	H11C—C11B—H11D	108.0
O1A—C12A—C13A	110.22 (16)	O1B—C12B—C13B	111.70 (17)
O1A—C12A—H12A	109.6	O1B—C12B—H12C	109.3
C13A—C12A—H12A	109.6	C13B—C12B—H12C	109.3
O1A—C12A—H12B	109.6	O1B—C12B—H12D	109.3
C13A—C12A—H12B	109.6	C13B—C12B—H12D	109.3
H12A—C12A—H12B	108.1	H12C—C12B—H12D	107.9
N5A—C13A—C12A	109.19 (15)	N5B—C13B—C12B	110.45 (15)
N5A—C13A—H13A	109.8	N5B—C13B—H13C	109.6
C12A—C13A—H13A	109.8	C12B—C13B—H13C	109.6
N5A—C13A—H13B	109.8	N5B—C13B—H13D	109.6
C12A—C13A—H13B	109.8	C12B—C13B—H13D	109.6
H13A—C13A—H13B	108.3	H13C—C13B—H13D	108.1
N4A—C14A—N2A	110.74 (15)	N4B—C14B—N2B	110.69 (14)
N4A—C14A—C15A	126.11 (15)	N4B—C14B—C15B	126.33 (14)
N2A—C14A—C15A	123.15 (15)	N2B—C14B—C15B	122.97 (14)
C14A—C15A—C16A	111.78 (14)	C14B—C15B—C16B	111.17 (13)
C14A—C15A—C26A	110.46 (15)	C14B—C15B—C26B	110.32 (14)
C16A—C15A—C26A	111.11 (14)	C16B—C15B—C26B	111.12 (13)
C14A—C15A—H15A	107.8	C14B—C15B—H15B	108.0
C16A—C15A—H15A	107.8	C16B—C15B—H15B	108.0
C26A—C15A—H15A	107.8	C26B—C15B—H15B	108.0
C17A—C16A—C21A	118.32 (16)	C21B—C16B—C17B	118.16 (16)
C17A—C16A—C15A	120.15 (16)	C21B—C16B—C15B	120.75 (15)
C21A—C16A—C15A	121.51 (16)	C17B—C16B—C15B	121.05 (14)
C18A—C17A—C16A	120.44 (17)	C18B—C17B—C16B	120.85 (16)
C18A—C17A—H17A	119.8	C18B—C17B—H17B	119.6
C16A—C17A—H17A	119.8	C16B—C17B—H17B	119.6
C19A—C18A—C17A	121.61 (17)	C17B—C18B—C19B	121.25 (16)
C19A—C18A—H18A	119.2	C17B—C18B—H18B	119.4
C17A—C18A—H18A	119.2	C19B—C18B—H18B	119.4
C18A—C19A—C20A	117.92 (17)	C18B—C19B—C20B	117.74 (16)
C18A—C19A—C22A	120.89 (17)	C18B—C19B—C22B	121.30 (16)
C20A—C19A—C22A	121.20 (17)	C20B—C19B—C22B	120.97 (15)
C21A—C20A—C19A	120.80 (16)	C21B—C20B—C19B	121.21 (16)
C21A—C20A—H20A	119.6	C21B—C20B—H20B	119.4
C19A—C20A—H20A	119.6	C19B—C20B—H20B	119.4
C20A—C21A—C16A	120.90 (16)	C20B—C21B—C16B	120.78 (16)
C20A—C21A—H21A	119.5	C20B—C21B—H21B	119.6
C16A—C21A—H21A	119.5	C16B—C21B—H21B	119.6
C19A—C22A—C23A	114.42 (17)	C19B—C22B—C23B	114.05 (13)
C19A—C22A—H22A	108.7	C19B—C22B—H22C	108.7
C23A—C22A—H22A	108.7	C23B—C22B—H22C	108.7
C19A—C22A—H22B	108.7	C19B—C22B—H22D	108.7
C23A—C22A—H22B	108.7	C23B—C22B—H22D	108.7
H22A—C22A—H22B	107.6	H22C—C22B—H22D	107.6
C25A—C23A—C22A	112.0 (2)	C24B—C23B—C25B	111.57 (14)
C25A—C23A—C24A	111.9 (2)	C24B—C23B—C22B	110.81 (14)
C22A—C23A—C24A	109.77 (19)	C25B—C23B—C22B	109.58 (14)
C25A—C23A—H23A	107.7	C24B—C23B—H23B	108.3
C22A—C23A—H23A	107.7	C25B—C23B—H23B	108.3
C24A—C23A—H23A	107.7	C22B—C23B—H23B	108.3
C23A—C24A—H24A	109.5	C23B—C24B—H24D	109.5
C23A—C24A—H24B	109.5	C23B—C24B—H24E	109.5
H24A—C24A—H24B	109.5	H24D—C24B—H24E	109.5
C23A—C24A—H24C	109.5	C23B—C24B—H24F	109.5
H24A—C24A—H24C	109.5	H24D—C24B—H24F	109.5
H24B—C24A—H24C	109.5	H24E—C24B—H24F	109.5
C23A—C25A—H25A	109.5	C23B—C25B—H25D	109.5
C23A—C25A—H25B	109.5	C23B—C25B—H25E	109.5
H25A—C25A—H25B	109.5	H25D—C25B—H25E	109.5
C23A—C25A—H25C	109.5	C23B—C25B—H25F	109.5
H25A—C25A—H25C	109.5	H25D—C25B—H25F	109.5
H25B—C25A—H25C	109.5	H25E—C25B—H25F	109.5
C15A—C26A—H26A	109.5	C15B—C26B—H26D	109.5
C15A—C26A—H26B	109.5	C15B—C26B—H26E	109.5
H26A—C26A—H26B	109.5	H26D—C26B—H26E	109.5
C15A—C26A—H26C	109.5	C15B—C26B—H26F	109.5
H26A—C26A—H26C	109.5	H26D—C26B—H26F	109.5
H26B—C26A—H26C	109.5	H26E—C26B—H26F	109.5

D—H···A	D—H	H···A	D···A	D—H···A
C7A—H7AA···S1A	0.93	2.46	3.195 (2)	137
C9A—H9AB···S1A	0.97	2.86	3.252 (2)	105
C4B—H4BA···N5Ai	0.93	2.56	3.384 (2)	147
C10A—H10A···Br1Aii	0.97	2.86	3.770 (2)	158
C7B—H7BA···S1B	0.93	2.56	3.190 (2)	125
C9B—H9BB···S1B	0.97	2.85	3.254 (2)	106
C15A—H15A···O1Aiii	0.98	2.29	3.244 (2)	165
C4A—H4AA···Cg1ii	0.93	2.53	3.401 (2)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7A—H7AA⋯S1A	0.93	2.46	3.195 (2)	137
C9A—H9AB⋯S1A	0.97	2.86	3.252 (2)	105
C4B—H4BA⋯N5Ai	0.93	2.56	3.384 (2)	147
C10A—H10A⋯Br1Aii	0.97	2.86	3.770 (2)	158
C7B—H7BA⋯S1B	0.93	2.56	3.190 (2)	125
C9B—H9BB⋯S1B	0.97	2.85	3.254 (2)	106
C15A—H15A⋯O1Aiii	0.98	2.29	3.244 (2)	165
C4A—H4AA⋯Cg1ii	0.93	2.53	3.401 (2)	156

Symmetry codes: (i) ; (ii) ; (iii) . Cg1 is the centroid of the C16A–C21A ring.