6-Bromo-3-{2-[2-(diphenyl-methyl-ene)hydrazin-yl]-1,3-thia-zol-5-yl}-2H-chromen-2-one chloro-form monosolvate.

In the title compound, C(25)H(16)BrN(3)O(2)S·CHCl(3), the thia-zole ring is approximately planar [maximum deviation = 0.002 (3) Å] and makes dihedral angles of 10.75 (14) and 87.75 (15)/2.80 (14)° with the pyran ring system and the two terminal phenyl rings, respectively. The solvent mol-ecule is disordered over two sets of sites, with refined occupancies of 0.639 (7) and 0.361 (7). In the crystal, mol-ecules are connected via pairs of weak C-H⋯O inter-actions, forming centrosymmetric dimers. An intra-molecular C-H⋯O hydrogen bond generates an S(6) ring motif.

Related literature

For details and applications of coumarin derivatives, see: Siddiqui et al. (2009 ▶); Kamal et al. (2009 ▶); Kalkhambkar et al. (2007 ▶); Gursoy & Karali (2003 ▶). For the synthesis of benzophenone thio­semicarbazone and 6-bromo-3-(2-bromo­acet­yl)-2H-chromen-2-one, see: Yaragatti et al. (2010 ▶); Lobana et al. (2006 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C25H16BrN3O2S·CHCl3

M = 621.75

Triclinic,

a = 8.0774 (3) Å

b = 12.6782 (5) Å

c = 14.4396 (5) Å

α = 114.157 (2)°

β = 92.879 (2)°

γ = 100.384 (2)°

V = 1314.40 (8) Å3

Z = 2

Mo Kα radiation

μ = 1.98 mm−1

T = 296 K

0.56 × 0.14 × 0.06 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009) ▶ T min = 0.401, T max = 0.891

21464 measured reflections

7663 independent reflections

3262 reflections with I > 2σ(I)

R int = 0.041

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.125

S = 1.00

7663 reflections

357 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.35 e Å−3

Δρmin = −0.40 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/S1600536811012335/lh5227sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811012335/lh5227Isup2.hkl

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

C25H16BrN3O2S·CHCl3	Z = 2
Mr = 621.75	F(000) = 624
Triclinic, P1	Dx = 1.571 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.0774 (3) Å	Cell parameters from 4500 reflections
b = 12.6782 (5) Å	θ = 2.9–29.6°
c = 14.4396 (5) Å	µ = 1.98 mm−1
α = 114.157 (2)°	T = 296 K
β = 92.879 (2)°	Plate, yellow
γ = 100.384 (2)°	0.56 × 0.14 × 0.06 mm
V = 1314.40 (8) Å3

Bruker SMART APEXII CCD area-detector diffractometer	7663 independent reflections
Radiation source: fine-focus sealed tube	3262 reflections with I > 2σ(I)
graphite	Rint = 0.041
φ and ω scans	θmax = 30.1°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
Tmin = 0.401, Tmax = 0.891	k = −17→17
21464 measured reflections	l = −20→20

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ2(Fo2) + (0.0487P)2 + 0.0043P] where P = (Fo2 + 2Fc2)/3
7663 reflections	(Δ/σ)max = 0.001
357 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.40 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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)
Br1	−0.38420 (5)	−0.63922 (3)	0.45724 (3)	0.09363 (18)
S1	0.38790 (9)	0.12055 (6)	0.50298 (6)	0.0610 (2)
O1	−0.1491 (2)	−0.32668 (16)	0.24872 (13)	0.0643 (5)
O2	0.0058 (3)	−0.17090 (17)	0.24065 (14)	0.0764 (6)
N1	0.2137 (3)	−0.03044 (18)	0.55842 (16)	0.0540 (5)
N2	0.3995 (3)	0.1301 (2)	0.69187 (19)	0.0651 (7)
N3	0.5130 (3)	0.23407 (18)	0.71595 (17)	0.0591 (6)
C1	−0.3766 (4)	−0.5695 (3)	0.2940 (2)	0.0740 (8)
H1A	−0.4596	−0.6386	0.2594	0.089*
C2	−0.3234 (4)	−0.4974 (2)	0.2462 (2)	0.0726 (8)
H2A	−0.3701	−0.5172	0.1795	0.087*
C3	−0.2001 (3)	−0.3959 (2)	0.2988 (2)	0.0568 (7)
C4	−0.0283 (3)	−0.2219 (2)	0.2938 (2)	0.0582 (7)
C5	0.0446 (3)	−0.1845 (2)	0.39995 (19)	0.0509 (6)
C6	−0.0045 (3)	−0.2545 (2)	0.44803 (19)	0.0540 (6)
H6A	0.0438	−0.2311	0.5152	0.065*
C7	−0.1285 (3)	−0.3632 (2)	0.39842 (19)	0.0529 (6)
C8	−0.1827 (4)	−0.4375 (2)	0.4461 (2)	0.0627 (7)
H8A	−0.1358	−0.4186	0.5126	0.075*
C9	−0.3070 (4)	−0.5392 (2)	0.3928 (2)	0.0651 (8)
C10	0.1692 (3)	−0.0710 (2)	0.45345 (19)	0.0505 (6)
C11	0.2498 (3)	−0.0017 (2)	0.4115 (2)	0.0580 (7)
H11A	0.2326	−0.0181	0.3423	0.070*
C12	0.3265 (3)	0.0681 (2)	0.5923 (2)	0.0540 (7)
C13	0.5912 (3)	0.2922 (2)	0.8078 (2)	0.0549 (6)
C14	0.5663 (4)	0.2503 (2)	0.8896 (2)	0.0569 (7)
C15	0.4327 (4)	0.2721 (3)	0.9451 (3)	0.0856 (10)
H15A	0.3585	0.3140	0.9318	0.103*
C16	0.4080 (5)	0.2325 (3)	1.0202 (3)	0.0930 (10)
H16A	0.3189	0.2494	1.0583	0.112*
C17	0.5125 (5)	0.1691 (3)	1.0390 (2)	0.0788 (9)
H17A	0.4941	0.1414	1.0889	0.095*
C18	0.6456 (4)	0.1458 (3)	0.9841 (2)	0.0775 (9)
H18A	0.7180	0.1026	0.9970	0.093*
C19	0.6724 (4)	0.1868 (2)	0.9093 (2)	0.0690 (8)
H19A	0.7630	0.1709	0.8723	0.083*
C20	0.7132 (3)	0.4042 (2)	0.8283 (2)	0.0567 (7)
C21	0.7536 (4)	0.4354 (2)	0.7496 (2)	0.0673 (8)
H21A	0.7037	0.3853	0.6828	0.081*
C22	0.8674 (4)	0.5400 (3)	0.7692 (3)	0.0784 (9)
H22A	0.8936	0.5599	0.7155	0.094*
C23	0.9421 (4)	0.6150 (3)	0.8679 (3)	0.0815 (9)
H23A	1.0189	0.6853	0.8811	0.098*
C24	0.9026 (4)	0.5853 (3)	0.9461 (3)	0.0789 (9)
H24A	0.9521	0.6361	1.0130	0.095*
C25	0.7901 (4)	0.4809 (2)	0.9271 (2)	0.0683 (8)
H25A	0.7654	0.4615	0.9812	0.082*
C26	0.9833 (5)	0.0897 (3)	0.2392 (3)	0.0975 (11)
H26A	0.9796	0.0622	0.2935	0.117*	0.372 (7)
H26B	0.9696	0.0357	0.2707	0.117*	0.628 (7)
Cl1A	0.8630 (12)	−0.0189 (3)	0.1341 (3)	0.136 (3)	0.372 (7)
Cl2A	1.1856 (9)	0.1392 (9)	0.2352 (8)	0.157 (3)	0.372 (7)
Cl3A	0.8588 (9)	0.2080 (4)	0.2724 (5)	0.0986 (14)	0.372 (7)
Cl1B	0.9957 (6)	0.0084 (4)	0.1053 (2)	0.1538 (16)	0.628 (7)
Cl2B	1.1788 (7)	0.1888 (3)	0.2910 (3)	0.1360 (14)	0.628 (7)
Cl3B	0.8225 (10)	0.1494 (8)	0.2524 (5)	0.213 (3)	0.628 (7)
H1N2	0.384 (4)	0.102 (3)	0.737 (2)	0.091 (11)*

	U11	U22	U33	U12	U13	U23
Br1	0.1128 (3)	0.0744 (2)	0.0971 (3)	−0.0036 (2)	0.0211 (2)	0.0490 (2)
S1	0.0596 (5)	0.0589 (4)	0.0710 (5)	0.0057 (3)	0.0107 (4)	0.0367 (4)
O1	0.0655 (12)	0.0705 (12)	0.0572 (11)	0.0013 (10)	−0.0032 (9)	0.0344 (9)
O2	0.0841 (15)	0.0871 (13)	0.0646 (12)	−0.0019 (11)	0.0008 (10)	0.0483 (11)
N1	0.0526 (13)	0.0562 (12)	0.0549 (14)	0.0093 (11)	0.0099 (11)	0.0263 (11)
N2	0.0742 (17)	0.0621 (14)	0.0549 (16)	0.0001 (13)	0.0053 (13)	0.0272 (13)
N3	0.0565 (14)	0.0509 (12)	0.0676 (16)	0.0045 (11)	0.0083 (12)	0.0261 (11)
C1	0.073 (2)	0.0605 (17)	0.079 (2)	−0.0024 (15)	0.0021 (17)	0.0286 (16)
C2	0.071 (2)	0.0718 (18)	0.0674 (19)	0.0002 (17)	−0.0081 (16)	0.0311 (16)
C3	0.0519 (16)	0.0585 (15)	0.0644 (18)	0.0090 (14)	0.0076 (14)	0.0320 (14)
C4	0.0489 (17)	0.0678 (17)	0.0636 (18)	0.0086 (14)	0.0065 (14)	0.0356 (15)
C5	0.0444 (15)	0.0606 (15)	0.0518 (15)	0.0123 (13)	0.0079 (12)	0.0275 (13)
C6	0.0555 (16)	0.0586 (15)	0.0479 (15)	0.0086 (13)	0.0062 (12)	0.0244 (13)
C7	0.0537 (16)	0.0541 (14)	0.0518 (16)	0.0113 (13)	0.0104 (13)	0.0235 (12)
C8	0.0709 (19)	0.0566 (16)	0.0599 (17)	0.0080 (15)	0.0134 (15)	0.0262 (14)
C9	0.071 (2)	0.0552 (16)	0.072 (2)	0.0083 (15)	0.0191 (16)	0.0304 (15)
C10	0.0460 (15)	0.0539 (14)	0.0576 (17)	0.0125 (12)	0.0084 (12)	0.0289 (13)
C11	0.0575 (17)	0.0646 (16)	0.0598 (16)	0.0117 (13)	0.0091 (13)	0.0348 (14)
C12	0.0498 (16)	0.0543 (15)	0.0647 (18)	0.0134 (13)	0.0140 (14)	0.0304 (14)
C13	0.0546 (16)	0.0530 (14)	0.0573 (17)	0.0130 (13)	0.0086 (14)	0.0230 (13)
C14	0.0532 (17)	0.0545 (15)	0.0578 (17)	0.0042 (14)	0.0013 (14)	0.0225 (13)
C15	0.083 (2)	0.113 (3)	0.090 (2)	0.043 (2)	0.030 (2)	0.062 (2)
C16	0.090 (3)	0.124 (3)	0.089 (2)	0.040 (2)	0.037 (2)	0.060 (2)
C17	0.092 (3)	0.078 (2)	0.068 (2)	0.0045 (19)	0.0092 (19)	0.0389 (17)
C18	0.088 (3)	0.0714 (19)	0.083 (2)	0.0185 (18)	0.005 (2)	0.0433 (17)
C19	0.0654 (19)	0.0707 (18)	0.080 (2)	0.0171 (16)	0.0148 (16)	0.0398 (17)
C20	0.0539 (17)	0.0526 (15)	0.0653 (18)	0.0127 (13)	0.0068 (14)	0.0266 (14)
C21	0.069 (2)	0.0631 (17)	0.0687 (19)	0.0103 (15)	0.0092 (15)	0.0289 (15)
C22	0.079 (2)	0.0716 (19)	0.093 (2)	0.0081 (17)	0.0210 (19)	0.0460 (19)
C23	0.074 (2)	0.0603 (18)	0.107 (3)	0.0039 (16)	0.006 (2)	0.038 (2)
C24	0.071 (2)	0.0663 (19)	0.086 (2)	0.0033 (17)	−0.0089 (17)	0.0267 (18)
C25	0.073 (2)	0.0603 (17)	0.071 (2)	0.0127 (16)	0.0038 (16)	0.0290 (16)
C26	0.118 (3)	0.095 (2)	0.098 (3)	0.022 (2)	−0.002 (2)	0.063 (2)
Cl1A	0.211 (7)	0.0912 (19)	0.097 (3)	0.014 (3)	−0.030 (3)	0.0435 (17)
Cl2A	0.108 (4)	0.223 (8)	0.229 (8)	0.052 (5)	0.074 (5)	0.171 (7)
Cl3A	0.117 (3)	0.107 (2)	0.098 (2)	0.055 (2)	0.0259 (19)	0.055 (2)
Cl1B	0.160 (3)	0.148 (2)	0.1210 (18)	0.065 (2)	0.0162 (18)	0.0132 (15)
Cl2B	0.174 (3)	0.1110 (18)	0.128 (2)	−0.0059 (17)	−0.007 (2)	0.0741 (17)
Cl3B	0.280 (6)	0.332 (7)	0.185 (4)	0.231 (6)	0.132 (4)	0.190 (5)

Br1—C9	1.898 (3)	C14—C19	1.370 (4)
S1—C11	1.716 (3)	C14—C15	1.377 (4)
S1—C12	1.732 (2)	C15—C16	1.379 (4)
O1—C3	1.372 (3)	C15—H15A	0.9300
O1—C4	1.379 (3)	C16—C17	1.353 (4)
O2—C4	1.202 (3)	C16—H16A	0.9300
N1—C12	1.295 (3)	C17—C18	1.371 (4)
N1—C10	1.390 (3)	C17—H17A	0.9300
N2—C12	1.362 (3)	C18—C19	1.387 (4)
N2—N3	1.363 (3)	C18—H18A	0.9300
N2—H1N2	0.87 (3)	C19—H19A	0.9300
N3—C13	1.284 (3)	C20—C21	1.382 (4)
C1—C9	1.375 (4)	C20—C25	1.387 (4)
C1—C2	1.378 (4)	C21—C22	1.383 (4)
C1—H1A	0.9300	C21—H21A	0.9300
C2—C3	1.373 (3)	C22—C23	1.378 (4)
C2—H2A	0.9300	C22—H22A	0.9300
C3—C7	1.384 (4)	C23—C24	1.364 (4)
C4—C5	1.461 (3)	C23—H23A	0.9300
C5—C6	1.353 (3)	C24—C25	1.378 (4)
C5—C10	1.473 (3)	C24—H24A	0.9300
C6—C7	1.428 (3)	C25—H25A	0.9300
C6—H6A	0.9300	C26—Cl3B	1.599 (7)
C7—C8	1.402 (3)	C26—Cl2A	1.655 (8)
C8—C9	1.381 (4)	C26—Cl1A	1.674 (5)
C8—H8A	0.9300	C26—Cl2B	1.740 (6)
C10—C11	1.354 (3)	C26—Cl1B	1.798 (5)
C11—H11A	0.9300	C26—Cl3A	1.869 (7)
C13—C20	1.483 (3)	C26—H26A	0.9800
C13—C14	1.488 (3)	C26—H26B	0.9601
C11—S1—C12	87.98 (13)	C16—C17—C18	119.8 (3)
C3—O1—C4	122.8 (2)	C16—C17—H17A	120.1
C12—N1—C10	109.2 (2)	C18—C17—H17A	120.1
C12—N2—N3	117.0 (2)	C17—C18—C19	120.0 (3)
C12—N2—H1N2	122 (2)	C17—C18—H18A	120.0
N3—N2—H1N2	120 (2)	C19—C18—H18A	120.0
C13—N3—N2	118.9 (2)	C14—C19—C18	120.4 (3)
C9—C1—C2	120.1 (3)	C14—C19—H19A	119.8
C9—C1—H1A	119.9	C18—C19—H19A	119.8
C2—C1—H1A	119.9	C21—C20—C25	118.1 (2)
C3—C2—C1	118.8 (3)	C21—C20—C13	121.0 (2)
C3—C2—H2A	120.6	C25—C20—C13	120.9 (2)
C1—C2—H2A	120.6	C20—C21—C22	120.8 (3)
O1—C3—C2	117.3 (2)	C20—C21—H21A	119.6
O1—C3—C7	120.5 (2)	C22—C21—H21A	119.6
C2—C3—C7	122.2 (2)	C23—C22—C21	120.2 (3)
O2—C4—O1	115.8 (2)	C23—C22—H22A	119.9
O2—C4—C5	126.9 (2)	C21—C22—H22A	119.9
O1—C4—C5	117.3 (2)	C24—C23—C22	119.5 (3)
C6—C5—C4	119.4 (2)	C24—C23—H23A	120.3
C6—C5—C10	120.9 (2)	C22—C23—H23A	120.3
C4—C5—C10	119.7 (2)	C23—C24—C25	120.6 (3)
C5—C6—C7	121.7 (2)	C23—C24—H24A	119.7
C5—C6—H6A	119.1	C25—C24—H24A	119.7
C7—C6—H6A	119.1	C24—C25—C20	120.8 (3)
C3—C7—C8	118.5 (2)	C24—C25—H25A	119.6
C3—C7—C6	118.3 (2)	C20—C25—H25A	119.6
C8—C7—C6	123.2 (2)	Cl3B—C26—Cl2A	132.4 (4)
C9—C8—C7	118.9 (3)	Cl3B—C26—Cl1A	85.1 (3)
C9—C8—H8A	120.5	Cl2A—C26—Cl1A	119.6 (4)
C7—C8—H8A	120.5	Cl3B—C26—Cl2B	115.0 (4)
C1—C9—C8	121.4 (2)	Cl2A—C26—Cl2B	27.3 (3)
C1—C9—Br1	119.3 (2)	Cl1A—C26—Cl2B	146.5 (4)
C8—C9—Br1	119.3 (2)	Cl3B—C26—Cl1B	110.0 (3)
C11—C10—N1	115.4 (2)	Cl2A—C26—Cl1B	79.3 (4)
C11—C10—C5	127.3 (2)	Cl1A—C26—Cl1B	40.7 (2)
N1—C10—C5	117.4 (2)	Cl2B—C26—Cl1B	105.8 (3)
C10—C11—S1	110.9 (2)	Cl3B—C26—Cl3A	20.7 (4)
C10—C11—H11A	124.6	Cl2A—C26—Cl3A	112.6 (4)
S1—C11—H11A	124.6	Cl1A—C26—Cl3A	102.1 (4)
N1—C12—N2	124.1 (2)	Cl2B—C26—Cl3A	94.4 (3)
N1—C12—S1	116.6 (2)	Cl1B—C26—Cl3A	116.5 (3)
N2—C12—S1	119.33 (19)	Cl3B—C26—H26A	101.7
N3—C13—C20	116.0 (2)	Cl2A—C26—H26A	107.3
N3—C13—C14	123.1 (2)	Cl1A—C26—H26A	107.3
C20—C13—C14	120.9 (2)	Cl2B—C26—H26A	95.1
C19—C14—C15	118.7 (3)	Cl1B—C26—H26A	129.1
C19—C14—C13	120.9 (3)	Cl3A—C26—H26A	107.3
C15—C14—C13	120.4 (3)	Cl3B—C26—H26B	108.6
C14—C15—C16	120.6 (3)	Cl2A—C26—H26B	112.0
C14—C15—H15A	119.7	Cl1A—C26—H26B	88.0
C16—C15—H15A	119.7	Cl2B—C26—H26B	108.5
C17—C16—C15	120.5 (3)	Cl1B—C26—H26B	108.8
C17—C16—H16A	119.8	Cl3A—C26—H26B	120.5
C15—C16—H16A	119.8	H26A—C26—H26B	20.9
C12—N2—N3—C13	−176.4 (2)	C12—S1—C11—C10	0.2 (2)
C9—C1—C2—C3	0.2 (5)	C10—N1—C12—N2	−178.7 (2)
C4—O1—C3—C2	179.0 (3)	C10—N1—C12—S1	0.3 (3)
C4—O1—C3—C7	−1.1 (4)	N3—N2—C12—N1	−178.3 (2)
C1—C2—C3—O1	179.5 (3)	N3—N2—C12—S1	2.8 (3)
C1—C2—C3—C7	−0.4 (5)	C11—S1—C12—N1	−0.3 (2)
C3—O1—C4—O2	179.1 (2)	C11—S1—C12—N2	178.7 (2)
C3—O1—C4—C5	−0.8 (4)	N2—N3—C13—C20	179.8 (2)
O2—C4—C5—C6	−178.0 (3)	N2—N3—C13—C14	1.1 (4)
O1—C4—C5—C6	1.9 (4)	N3—C13—C14—C19	94.4 (3)
O2—C4—C5—C10	2.5 (4)	C20—C13—C14—C19	−84.2 (3)
O1—C4—C5—C10	−177.6 (2)	N3—C13—C14—C15	−83.9 (4)
C4—C5—C6—C7	−1.2 (4)	C20—C13—C14—C15	97.5 (3)
C10—C5—C6—C7	178.3 (2)	C19—C14—C15—C16	1.1 (5)
O1—C3—C7—C8	−179.1 (2)	C13—C14—C15—C16	179.3 (3)
C2—C3—C7—C8	0.8 (4)	C14—C15—C16—C17	−1.5 (5)
O1—C3—C7—C6	1.8 (4)	C15—C16—C17—C18	1.1 (5)
C2—C3—C7—C6	−178.3 (3)	C16—C17—C18—C19	−0.3 (5)
C5—C6—C7—C3	−0.6 (4)	C15—C14—C19—C18	−0.3 (4)
C5—C6—C7—C8	−179.7 (3)	C13—C14—C19—C18	−178.5 (3)
C3—C7—C8—C9	−1.0 (4)	C17—C18—C19—C14	−0.1 (4)
C6—C7—C8—C9	178.1 (3)	N3—C13—C20—C21	−7.5 (4)
C2—C1—C9—C8	−0.4 (5)	C14—C13—C20—C21	171.2 (3)
C2—C1—C9—Br1	179.4 (2)	N3—C13—C20—C25	172.5 (3)
C7—C8—C9—C1	0.8 (4)	C14—C13—C20—C25	−8.8 (4)
C7—C8—C9—Br1	−179.0 (2)	C25—C20—C21—C22	0.0 (4)
C12—N1—C10—C11	−0.1 (3)	C13—C20—C21—C22	179.9 (3)
C12—N1—C10—C5	178.5 (2)	C20—C21—C22—C23	−0.1 (5)
C6—C5—C10—C11	168.7 (3)	C21—C22—C23—C24	−0.2 (5)
C4—C5—C10—C11	−11.8 (4)	C22—C23—C24—C25	0.5 (5)
C6—C5—C10—N1	−9.7 (4)	C23—C24—C25—C20	−0.7 (5)
C4—C5—C10—N1	169.8 (2)	C21—C20—C25—C24	0.4 (4)
N1—C10—C11—S1	−0.1 (3)	C13—C20—C25—C24	−179.6 (3)
C5—C10—C11—S1	−178.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O2	0.93	2.32	2.868 (4)	117
C19—H19A···O2i	0.93	2.54	3.448 (4)	165
C26—H26B···O2ii	0.96	2.55	3.350 (5)	141

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯O2	0.93	2.32	2.868 (4)	117
C19—H19A⋯O2i	0.93	2.54	3.448 (4)	165
C26—H26B⋯O2ii	0.96	2.55	3.350 (5)	141

Symmetry codes: (i) ; (ii) .