3-Benzyl-7-bromo-9-phenyl-2-tosyl-2,3,3a,4,9,9a-hexa-hydro-1H-pyrrolo[3,4-b]quinoline.

In the title compound, C(31)H(29)BrN(2)O(2)S, the pyrrolidine ring is in a twist conformation and the tetra-hydro-pyridine ring adopts an envelope conformation with the methine C atom adjacent to the NH group as the flap atom; the two rings are trans-fused. The bromo-benzene ring and the nearest phenyl ring form a dihedral angle of 82.72 (10)°. The benzyl phenyl and the tosyl phenyl rings are oriented at a dihedral angle of 75.57 (11)°. An intra-molecular N-H⋯π inter-action is observed. In the crystal, mol-ecules are linked into chains running along [101] by C-H⋯O hydrogen bonds and the chains are cross-linked via weak C-H⋯π inter-actions.

Related literature

For the biological activity of pyrroloquinoline derivatives, see: Peng et al. (2002 ▶); Metobo et al. (2009 ▶); Ferlin et al. (2005 ▶); Ryu et al. (2009 ▶); Tsuji et al. (1995 ▶); Ferlin et al. (2001 ▶). For the crystal structures of chlorine and unbrominated analogues, see: Chinnakali et al. (2009a ▶,b ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶). For asymmetry parameters, see: Duax et al. (1976 ▶).

Experimental

Crystal data

C31H29BrN2O2S

M = 573.53

Monoclinic,

a = 8.8992 (2) Å

b = 27.5824 (5) Å

c = 13.3668 (2) Å

β = 127.190 (1)°

V = 2613.78 (9) Å3

Z = 4

Mo Kα radiation

μ = 1.69 mm−1

T = 100 K

0.39 × 0.28 × 0.13 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.641, T max = 0.805

43436 measured reflections

7624 independent reflections

6348 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.096

S = 1.06

7624 reflections

339 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.82 e Å−3

Δρmin = −0.71 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/S1600536809045875/hb5202sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809045875/hb5202Isup2.hkl

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

C31H29BrN2O2S	F(000) = 1184
Mr = 573.53	Dx = 1.457 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9860 reflections
a = 8.8992 (2) Å	θ = 2.4–37.0°
b = 27.5824 (5) Å	µ = 1.69 mm−1
c = 13.3668 (2) Å	T = 100 K
β = 127.190 (1)°	Block, colourless
V = 2613.78 (9) Å3	0.39 × 0.28 × 0.13 mm
Z = 4

Bruker SMART APEXII CCD diffractometer	7624 independent reflections
Radiation source: fine-focus sealed tube	6348 reflections with I > 2σ(I)
graphite	Rint = 0.034
φ and ω scans	θmax = 30.0°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→12
Tmin = 0.641, Tmax = 0.805	k = −35→38
43436 measured reflections	l = −18→16

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ2(Fo2) + (0.0447P)2 + 2.281P] where P = (Fo2 + 2Fc2)/3
7624 reflections	(Δ/σ)max = 0.001
339 parameters	Δρmax = 0.82 e Å−3
0 restraints	Δρmin = −0.71 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
Br1	−0.02354 (3)	0.121549 (7)	0.223962 (19)	0.01926 (6)
S1	1.38753 (6)	0.137930 (17)	0.96077 (4)	0.01528 (10)
O1	1.4895 (2)	0.12512 (5)	0.91282 (14)	0.0208 (3)
O2	1.46953 (19)	0.17022 (5)	1.06590 (13)	0.0203 (3)
N1	1.1910 (2)	0.16359 (6)	0.84519 (15)	0.0142 (3)
N2	0.7082 (2)	0.15745 (6)	0.74366 (15)	0.0142 (3)
H1N2	0.698 (4)	0.1741 (10)	0.791 (3)	0.029 (7)*
C1	1.0890 (3)	0.14242 (7)	0.71672 (18)	0.0162 (4)
H1A	1.1538	0.1140	0.7175	0.019*
H1B	1.0766	0.1659	0.6582	0.019*
C2	0.8972 (3)	0.12908 (6)	0.68243 (17)	0.0132 (3)
H2	0.9089	0.0988	0.7250	0.016*
C3	0.7325 (3)	0.12458 (6)	0.54317 (17)	0.0131 (3)
H3	0.7436	0.1510	0.4990	0.016*
C4	0.5476 (3)	0.13198 (6)	0.52621 (17)	0.0128 (3)
C5	0.3766 (3)	0.12455 (6)	0.40768 (18)	0.0147 (3)
H5	0.3776	0.1149	0.3414	0.018*
C6	0.2054 (3)	0.13134 (6)	0.38721 (18)	0.0148 (4)
C7	0.2001 (3)	0.14504 (7)	0.48506 (19)	0.0167 (4)
H7	0.0853	0.1487	0.4717	0.020*
C8	0.3676 (3)	0.15308 (7)	0.60239 (19)	0.0160 (4)
H8	0.3647	0.1623	0.6681	0.019*
C9	0.5425 (3)	0.14763 (6)	0.62462 (17)	0.0129 (3)
C10	0.8645 (2)	0.17057 (7)	0.74190 (17)	0.0125 (3)
H10	0.8312	0.1998	0.6908	0.015*
C11	1.0543 (2)	0.17848 (7)	0.87013 (17)	0.0133 (3)
H11	1.0652	0.1564	0.9316	0.016*
C12	1.3304 (3)	0.08391 (7)	1.00181 (18)	0.0159 (4)
C13	1.3157 (3)	0.08395 (8)	1.09972 (19)	0.0217 (4)
H13	1.3314	0.1126	1.1416	0.026*
C14	1.2775 (3)	0.04104 (8)	1.1346 (2)	0.0247 (4)
H14	1.2671	0.0413	1.1998	0.030*
C15	1.2546 (3)	−0.00222 (8)	1.0741 (2)	0.0203 (4)
C16	1.2670 (3)	−0.00143 (8)	0.9752 (2)	0.0255 (4)
H16	1.2495	−0.0300	0.9326	0.031*
C17	1.3049 (3)	0.04111 (8)	0.9388 (2)	0.0245 (4)
H17	1.3132	0.0409	0.8727	0.029*
C18	1.2250 (3)	−0.04916 (8)	1.1177 (2)	0.0256 (4)
H18A	1.1229	−0.0455	1.1232	0.038*
H18B	1.3381	−0.0575	1.1988	0.038*
H18C	1.1952	−0.0744	1.0589	0.038*
C19	0.7354 (2)	0.07718 (7)	0.48649 (17)	0.0132 (3)
C20	0.7079 (3)	0.03291 (7)	0.52376 (19)	0.0192 (4)
H20	0.6864	0.0324	0.5837	0.023*
C21	0.7122 (3)	−0.01038 (7)	0.4725 (2)	0.0227 (4)
H21	0.6936	−0.0396	0.4982	0.027*
C22	0.7443 (3)	−0.00997 (8)	0.3832 (2)	0.0233 (4)
H22	0.7474	−0.0389	0.3489	0.028*
C23	0.7717 (3)	0.03359 (8)	0.3452 (2)	0.0234 (4)
H23	0.7941	0.0339	0.2857	0.028*
C24	0.7656 (3)	0.07699 (7)	0.39584 (18)	0.0170 (4)
H24	0.7820	0.1062	0.3688	0.020*
C25	1.0855 (3)	0.23088 (7)	0.91806 (18)	0.0163 (4)
H25A	1.2055	0.2335	1.0008	0.020*
H25B	1.0872	0.2527	0.8618	0.020*
C26	0.9258 (3)	0.24439 (7)	0.92394 (18)	0.0149 (3)
C27	0.7728 (3)	0.27179 (7)	0.82900 (18)	0.0171 (4)
H27	0.7786	0.2870	0.7693	0.021*
C28	0.6109 (3)	0.27661 (7)	0.82256 (19)	0.0190 (4)
H28	0.5094	0.2948	0.7585	0.023*
C29	0.6011 (3)	0.25435 (7)	0.9116 (2)	0.0209 (4)
H29	0.4921	0.2568	0.9062	0.025*
C30	0.7551 (3)	0.22835 (7)	1.00898 (19)	0.0196 (4)
H30	0.7502	0.2139	1.0698	0.023*
C31	0.9168 (3)	0.22381 (7)	1.01571 (19)	0.0182 (4)
H31	1.0201	0.2069	1.0821	0.022*

	U11	U22	U33	U12	U13	U23
Br1	0.01373 (9)	0.02465 (11)	0.01461 (10)	−0.00055 (7)	0.00604 (8)	0.00078 (7)
S1	0.0108 (2)	0.0186 (2)	0.0157 (2)	−0.00166 (16)	0.00767 (18)	−0.00202 (17)
O1	0.0163 (7)	0.0261 (8)	0.0243 (8)	0.0000 (5)	0.0145 (6)	−0.0017 (6)
O2	0.0145 (6)	0.0236 (7)	0.0181 (7)	−0.0042 (5)	0.0074 (6)	−0.0054 (6)
N1	0.0106 (7)	0.0202 (8)	0.0121 (7)	0.0001 (6)	0.0071 (6)	−0.0012 (6)
N2	0.0133 (7)	0.0189 (8)	0.0134 (7)	−0.0022 (6)	0.0098 (6)	−0.0043 (6)
C1	0.0136 (8)	0.0216 (9)	0.0150 (9)	−0.0010 (7)	0.0095 (7)	−0.0023 (7)
C2	0.0143 (8)	0.0140 (9)	0.0122 (8)	−0.0008 (6)	0.0085 (7)	−0.0008 (6)
C3	0.0147 (8)	0.0136 (8)	0.0133 (8)	0.0001 (6)	0.0097 (7)	0.0004 (7)
C4	0.0145 (8)	0.0118 (8)	0.0159 (9)	0.0000 (6)	0.0113 (7)	0.0002 (6)
C5	0.0180 (9)	0.0128 (8)	0.0132 (8)	−0.0001 (6)	0.0094 (7)	0.0003 (7)
C6	0.0152 (8)	0.0131 (8)	0.0126 (8)	0.0002 (6)	0.0065 (7)	0.0005 (6)
C7	0.0152 (8)	0.0165 (9)	0.0210 (9)	0.0013 (7)	0.0123 (8)	0.0004 (7)
C8	0.0167 (9)	0.0178 (9)	0.0181 (9)	−0.0007 (7)	0.0129 (8)	−0.0022 (7)
C9	0.0142 (8)	0.0121 (8)	0.0138 (8)	−0.0003 (6)	0.0092 (7)	0.0002 (6)
C10	0.0143 (8)	0.0138 (8)	0.0113 (8)	−0.0010 (6)	0.0088 (7)	−0.0008 (6)
C11	0.0129 (8)	0.0164 (9)	0.0123 (8)	−0.0004 (6)	0.0084 (7)	−0.0010 (7)
C12	0.0129 (8)	0.0179 (9)	0.0140 (9)	0.0008 (7)	0.0066 (7)	0.0003 (7)
C13	0.0288 (11)	0.0217 (10)	0.0161 (9)	−0.0002 (8)	0.0144 (9)	−0.0021 (8)
C14	0.0318 (12)	0.0256 (11)	0.0208 (10)	0.0016 (9)	0.0180 (10)	0.0017 (8)
C15	0.0152 (9)	0.0222 (10)	0.0218 (10)	0.0010 (7)	0.0103 (8)	0.0029 (8)
C16	0.0346 (12)	0.0185 (10)	0.0288 (11)	−0.0033 (8)	0.0220 (10)	−0.0048 (8)
C17	0.0315 (11)	0.0240 (11)	0.0242 (11)	−0.0025 (9)	0.0201 (10)	−0.0032 (8)
C18	0.0242 (11)	0.0233 (11)	0.0283 (12)	0.0004 (8)	0.0153 (10)	0.0046 (9)
C19	0.0105 (8)	0.0179 (9)	0.0106 (8)	0.0005 (6)	0.0060 (7)	−0.0007 (7)
C20	0.0238 (10)	0.0192 (10)	0.0204 (10)	0.0022 (7)	0.0164 (9)	0.0014 (8)
C21	0.0259 (10)	0.0152 (9)	0.0295 (11)	0.0014 (8)	0.0182 (10)	0.0009 (8)
C22	0.0249 (10)	0.0191 (10)	0.0266 (11)	0.0016 (8)	0.0159 (9)	−0.0063 (8)
C23	0.0271 (11)	0.0273 (11)	0.0236 (11)	−0.0020 (8)	0.0194 (9)	−0.0063 (8)
C24	0.0166 (9)	0.0203 (9)	0.0162 (9)	−0.0031 (7)	0.0111 (8)	−0.0020 (7)
C25	0.0152 (8)	0.0173 (9)	0.0169 (9)	−0.0033 (7)	0.0100 (8)	−0.0030 (7)
C26	0.0173 (9)	0.0142 (8)	0.0144 (9)	−0.0031 (7)	0.0101 (7)	−0.0045 (7)
C27	0.0233 (10)	0.0145 (9)	0.0168 (9)	−0.0010 (7)	0.0139 (8)	−0.0014 (7)
C28	0.0202 (9)	0.0174 (9)	0.0186 (9)	0.0019 (7)	0.0114 (8)	−0.0012 (7)
C29	0.0226 (10)	0.0196 (10)	0.0261 (11)	−0.0015 (8)	0.0176 (9)	−0.0043 (8)
C30	0.0289 (10)	0.0174 (9)	0.0199 (10)	−0.0032 (8)	0.0186 (9)	−0.0027 (7)
C31	0.0216 (9)	0.0176 (9)	0.0152 (9)	0.0004 (7)	0.0111 (8)	−0.0007 (7)

Br1—C6	1.9002 (19)	C14—C15	1.385 (3)
S1—O2	1.4356 (15)	C14—H14	0.93
S1—O1	1.4364 (15)	C15—C16	1.392 (3)
S1—N1	1.6369 (16)	C15—C18	1.507 (3)
S1—C12	1.765 (2)	C16—C17	1.387 (3)
N1—C1	1.493 (2)	C16—H16	0.93
N1—C11	1.500 (2)	C17—H17	0.93
N2—C9	1.394 (2)	C18—H18A	0.96
N2—C10	1.451 (2)	C18—H18B	0.96
N2—H1N2	0.83 (3)	C18—H18C	0.96
C1—C2	1.520 (3)	C19—C24	1.391 (3)
C1—H1A	0.97	C19—C20	1.395 (3)
C1—H1B	0.97	C20—C21	1.388 (3)
C2—C10	1.519 (2)	C20—H20	0.93
C2—C3	1.527 (3)	C21—C22	1.385 (3)
C2—H2	0.98	C21—H21	0.93
C3—C19	1.519 (2)	C22—C23	1.383 (3)
C3—C4	1.533 (2)	C22—H22	0.93
C3—H3	0.98	C23—C24	1.393 (3)
C4—C5	1.397 (3)	C23—H23	0.93
C4—C9	1.411 (2)	C24—H24	0.93
C5—C6	1.388 (3)	C25—C26	1.516 (3)
C5—H5	0.93	C25—H25A	0.97
C6—C7	1.389 (3)	C25—H25B	0.97
C7—C8	1.380 (3)	C26—C27	1.396 (3)
C7—H7	0.93	C26—C31	1.398 (3)
C8—C9	1.405 (2)	C27—C28	1.397 (3)
C8—H8	0.93	C27—H27	0.93
C10—C11	1.529 (3)	C28—C29	1.388 (3)
C10—H10	0.98	C28—H28	0.93
C11—C25	1.537 (3)	C29—C30	1.389 (3)
C11—H11	0.98	C29—H29	0.93
C12—C17	1.387 (3)	C30—C31	1.391 (3)
C12—C13	1.392 (3)	C30—H30	0.93
C13—C14	1.388 (3)	C31—H31	0.93
C13—H13	0.93
O2—S1—O1	120.33 (9)	C14—C13—C12	119.79 (19)
O2—S1—N1	106.05 (9)	C14—C13—H13	120.1
O1—S1—N1	106.73 (8)	C12—C13—H13	120.1
O2—S1—C12	106.91 (9)	C15—C14—C13	121.2 (2)
O1—S1—C12	108.03 (9)	C15—C14—H14	119.4
N1—S1—C12	108.31 (9)	C13—C14—H14	119.4
C1—N1—C11	110.57 (14)	C14—C15—C16	118.21 (19)
C1—N1—S1	118.47 (13)	C14—C15—C18	120.84 (19)
C11—N1—S1	117.12 (12)	C16—C15—C18	120.90 (19)
C9—N2—C10	113.13 (15)	C17—C16—C15	121.5 (2)
C9—N2—H1N2	116.8 (19)	C17—C16—H16	119.3
C10—N2—H1N2	114.8 (18)	C15—C16—H16	119.3
N1—C1—C2	103.47 (14)	C12—C17—C16	119.5 (2)
N1—C1—H1A	111.1	C12—C17—H17	120.3
C2—C1—H1A	111.1	C16—C17—H17	120.3
N1—C1—H1B	111.1	C15—C18—H18A	109.5
C2—C1—H1B	111.1	C15—C18—H18B	109.5
H1A—C1—H1B	109.0	H18A—C18—H18B	109.5
C10—C2—C1	101.27 (14)	C15—C18—H18C	109.5
C10—C2—C3	110.67 (15)	H18A—C18—H18C	109.5
C1—C2—C3	117.55 (15)	H18B—C18—H18C	109.5
C10—C2—H2	109.0	C24—C19—C20	118.40 (17)
C1—C2—H2	109.0	C24—C19—C3	120.53 (17)
C3—C2—H2	109.0	C20—C19—C3	121.07 (16)
C19—C3—C2	112.66 (15)	C21—C20—C19	120.90 (18)
C19—C3—C4	112.38 (15)	C21—C20—H20	119.6
C2—C3—C4	108.85 (15)	C19—C20—H20	119.6
C19—C3—H3	107.6	C22—C21—C20	119.98 (19)
C2—C3—H3	107.6	C22—C21—H21	120.0
C4—C3—H3	107.6	C20—C21—H21	120.0
C5—C4—C9	118.36 (17)	C23—C22—C21	119.88 (19)
C5—C4—C3	118.95 (16)	C23—C22—H22	120.1
C9—C4—C3	122.66 (16)	C21—C22—H22	120.1
C6—C5—C4	121.12 (17)	C22—C23—C24	120.05 (19)
C6—C5—H5	119.4	C22—C23—H23	120.0
C4—C5—H5	119.4	C24—C23—H23	120.0
C5—C6—C7	120.60 (18)	C19—C24—C23	120.78 (19)
C5—C6—Br1	119.63 (14)	C19—C24—H24	119.6
C7—C6—Br1	119.78 (14)	C23—C24—H24	119.6
C8—C7—C6	119.03 (17)	C26—C25—C11	108.30 (15)
C8—C7—H7	120.5	C26—C25—H25A	110.0
C6—C7—H7	120.5	C11—C25—H25A	110.0
C7—C8—C9	121.38 (17)	C26—C25—H25B	110.0
C7—C8—H8	119.3	C11—C25—H25B	110.0
C9—C8—H8	119.3	H25A—C25—H25B	108.4
N2—C9—C8	119.53 (16)	C27—C26—C31	118.40 (17)
N2—C9—C4	121.04 (16)	C27—C26—C25	121.08 (17)
C8—C9—C4	119.44 (17)	C31—C26—C25	119.92 (17)
N2—C10—C2	108.05 (15)	C26—C27—C28	120.74 (18)
N2—C10—C11	115.96 (15)	C26—C27—H27	119.6
C2—C10—C11	105.22 (14)	C28—C27—H27	119.6
N2—C10—H10	109.1	C29—C28—C27	120.12 (19)
C2—C10—H10	109.1	C29—C28—H28	119.9
C11—C10—H10	109.1	C27—C28—H28	119.9
N1—C11—C10	101.94 (13)	C28—C29—C30	119.60 (18)
N1—C11—C25	112.56 (15)	C28—C29—H29	120.2
C10—C11—C25	113.59 (15)	C30—C29—H29	120.2
N1—C11—H11	109.5	C29—C30—C31	120.21 (18)
C10—C11—H11	109.5	C29—C30—H30	119.9
C25—C11—H11	109.5	C31—C30—H30	119.9
C17—C12—C13	119.84 (19)	C30—C31—C26	120.83 (19)
C17—C12—S1	120.14 (15)	C30—C31—H31	119.6
C13—C12—S1	120.00 (15)	C26—C31—H31	119.6
O2—S1—N1—C1	170.23 (13)	C2—C10—C11—N1	30.32 (17)
O1—S1—N1—C1	40.79 (15)	N2—C10—C11—C25	−89.02 (19)
C12—S1—N1—C1	−75.31 (15)	C2—C10—C11—C25	151.67 (15)
O2—S1—N1—C11	−53.17 (15)	O2—S1—C12—C17	−159.73 (17)
O1—S1—N1—C11	177.39 (13)	O1—S1—C12—C17	−28.88 (19)
C12—S1—N1—C11	61.30 (15)	N1—S1—C12—C17	86.37 (18)
C11—N1—C1—C2	−18.81 (19)	O2—S1—C12—C13	18.59 (18)
S1—N1—C1—C2	120.42 (14)	O1—S1—C12—C13	149.44 (16)
N1—C1—C2—C10	36.53 (17)	N1—S1—C12—C13	−95.31 (17)
N1—C1—C2—C3	157.19 (15)	C17—C12—C13—C14	0.7 (3)
C10—C2—C3—C19	−166.61 (15)	S1—C12—C13—C14	−177.66 (16)
C1—C2—C3—C19	77.8 (2)	C12—C13—C14—C15	0.4 (3)
C10—C2—C3—C4	−41.27 (19)	C13—C14—C15—C16	−1.3 (3)
C1—C2—C3—C4	−156.90 (15)	C13—C14—C15—C18	176.2 (2)
C19—C3—C4—C5	−48.0 (2)	C14—C15—C16—C17	1.2 (3)
C2—C3—C4—C5	−173.54 (16)	C18—C15—C16—C17	−176.3 (2)
C19—C3—C4—C9	134.17 (17)	C13—C12—C17—C16	−0.7 (3)
C2—C3—C4—C9	8.7 (2)	S1—C12—C17—C16	177.61 (17)
C9—C4—C5—C6	−1.4 (3)	C15—C16—C17—C12	−0.2 (3)
C3—C4—C5—C6	−179.24 (16)	C2—C3—C19—C24	−113.59 (19)
C4—C5—C6—C7	−1.0 (3)	C4—C3—C19—C24	123.01 (18)
C4—C5—C6—Br1	179.26 (13)	C2—C3—C19—C20	66.4 (2)
C5—C6—C7—C8	1.7 (3)	C4—C3—C19—C20	−57.0 (2)
Br1—C6—C7—C8	−178.53 (14)	C24—C19—C20—C21	0.6 (3)
C6—C7—C8—C9	−0.1 (3)	C3—C19—C20—C21	−179.42 (18)
C10—N2—C9—C8	−155.20 (17)	C19—C20—C21—C22	0.0 (3)
C10—N2—C9—C4	25.2 (2)	C20—C21—C22—C23	−0.1 (3)
C7—C8—C9—N2	178.18 (18)	C21—C22—C23—C24	−0.5 (3)
C7—C8—C9—C4	−2.2 (3)	C20—C19—C24—C23	−1.1 (3)
C5—C4—C9—N2	−177.51 (17)	C3—C19—C24—C23	178.86 (18)
C3—C4—C9—N2	0.3 (3)	C22—C23—C24—C19	1.1 (3)
C5—C4—C9—C8	2.9 (3)	N1—C11—C25—C26	172.70 (15)
C3—C4—C9—C8	−179.28 (16)	C10—C11—C25—C26	57.5 (2)
C9—N2—C10—C2	−58.2 (2)	C11—C25—C26—C27	−99.7 (2)
C9—N2—C10—C11	−175.99 (15)	C11—C25—C26—C31	71.3 (2)
C1—C2—C10—N2	−166.58 (15)	C31—C26—C27—C28	−3.0 (3)
C3—C2—C10—N2	68.01 (18)	C25—C26—C27—C28	168.13 (18)
C1—C2—C10—C11	−42.12 (17)	C26—C27—C28—C29	0.5 (3)
C3—C2—C10—C11	−167.53 (14)	C27—C28—C29—C30	1.7 (3)
C1—N1—C11—C10	−6.89 (19)	C28—C29—C30—C31	−1.3 (3)
S1—N1—C11—C10	−146.72 (12)	C29—C30—C31—C26	−1.2 (3)
C1—N1—C11—C25	−128.95 (16)	C27—C26—C31—C30	3.3 (3)
S1—N1—C11—C25	91.22 (17)	C25—C26—C31—C30	−167.86 (18)
N2—C10—C11—N1	149.63 (15)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O1	0.97	2.53	2.917 (3)	104
C13—H13···O2	0.93	2.56	2.914 (3)	103
C28—H28···O2i	0.93	2.57	3.207 (3)	126
N2—H1N2···Cg3	0.83 (3)	2.53 (3)	3.289 (2)	152 (3)
C3—H3···Cg3ii	0.98	2.98	3.924 (2)	162
C18—H18A···Cg2iii	0.96	2.94	3.737 (3)	141
C21—H21···Cg1iv	0.93	2.80	3.676 (2)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C28—H28⋯O2i	0.93	2.57	3.207 (3)	126
N2—H1N2⋯Cg3	0.83 (3)	2.53 (3)	3.289 (2)	152 (3)
C3—H3⋯Cg3ii	0.98	2.98	3.924 (2)	162
C18—H18A⋯Cg2iii	0.96	2.94	3.737 (3)	141
C21—H21⋯Cg1iv	0.93	2.80	3.676 (2)	158

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) . Cg1, Cg2 and Cg3 are the centroids of the C4–C9, C12–C17 and C26–C31 rings, respectively.