Darifenacin hydro-bromide.

In the title compound {systematic name: (S)-3-[(aminocar-bonyl)diphenylmethyl]-1-[2-(2,3-di-hy-dro-benzofuran-5-yl)ethyl]pyrrolidinium bromide}, C(28)H(31)N(2)O(2) (+)·Br(-), the pyrrolidine rings adopts an envelope conformation. The two phenyl rings make a dihedral angle of 72.5 (1)°. The four coplanar atoms of the pyrrolidine ring makes dihedral angles of 33.1 (2) and 82.8 (2)° with the two phenyl rings. The mol-ecular conformation is influenced by a C-H⋯O inter-action. In the crystal packing, there are two N-H⋯Br hydrogen bonds running in opposite directions. They appear to form C(10) and C(9) chain motifs in the unit cell. In addition, the mol-ecular packing is further stabilized by C-H⋯Br and C-H⋯O hydrogen bonds. The C atom bonded to the benzofuran ring system is disordered in a 0.66:0.34 ratio.

Related literature

For general background to darifenacin derivatives, see: Chapple (2004 ▶); Croom & Keating (2004 ▶); Haab et al. (2004 ▶); Levin et al. (2008 ▶). For bond-length data, see: Allen et al. (1987 ▶); Selvanayagam et al. (2005 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C28H31N2O2 +·Br−

M = 507.46

Orthorhombic,

a = 10.2632 (7) Å

b = 10.9525 (8) Å

c = 21.7459 (16) Å

V = 2444.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 1.71 mm−1

T = 293 K

0.24 × 0.22 × 0.20 mm

Data collection

Bruker SMART APEX CCD area-detector diffractometer

Absorption correction: none

27916 measured reflections

5777 independent reflections

4703 reflections with I > 2σ(I)

R int = 0.065

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.121

S = 1.07

5777 reflections

315 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.55 e Å−3

Δρmin = −0.84 e Å−3

Absolute structure: Flack (1983 ▶), 2471 Friedel pairs

Flack parameter: 0.005 (13)

Data collection: SMART (Bruker, 2001 ▶); cell refinement: SAINT (Bruker, 2001 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809017085/bt2946sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809017085/bt2946Isup2.hkl

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

C28H31N2O2+·Br−	F(000) = 1056
Mr = 507.46	Dx = 1.379 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 18484 reflections
a = 10.2632 (7) Å	θ = 2.1–24.9°
b = 10.9525 (8) Å	µ = 1.71 mm−1
c = 21.7459 (16) Å	T = 293 K
V = 2444.4 (3) Å3	Block, colourless
Z = 4	0.24 × 0.22 × 0.20 mm

Bruker SMART APEX CCD area-detector diffractometer	4703 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.065
graphite	θmax = 28.0°, θmin = 1.9°
ω scans	h = −13→13
27916 measured reflections	k = −14→14
5777 independent reflections	l = −28→28

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)] = 0.054	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.121	w = 1/[σ2(Fo2) + (0.030P)2 + 2.3972P] where P = (Fo2 + 2Fc2)/3
S = 1.07	(Δ/σ)max < 0.001
5777 reflections	Δρmax = 0.55 e Å−3
315 parameters	Δρmin = −0.84 e Å−3
2 restraints	Absolute structure: Flack (1983), 2471 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.005 (13)

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)
Br1	0.20755 (4)	0.88262 (6)	0.09168 (2)	0.07287 (18)
O1	0.8147 (3)	0.9481 (3)	1.04271 (14)	0.0553 (8)
O2	0.2700 (4)	0.7835 (4)	0.66039 (17)	0.0893 (13)
N1	0.4854 (5)	0.8538 (3)	1.00332 (19)	0.0796 (14)
H1	0.4034	0.8587	1.0190	0.096*
N2	0.9041 (4)	1.0090 (4)	1.1310 (2)	0.0599 (10)
H2NA	0.899 (6)	1.047 (5)	1.1657 (14)	0.08 (2)*
H2NB	0.979 (3)	0.977 (5)	1.124 (3)	0.088 (19)*
C1	0.5303 (4)	0.9721 (3)	1.02376 (18)	0.0430 (9)
H1A	0.4634	1.0334	1.0175	0.052*
H1B	0.6079	0.9963	1.0014	0.052*
C2	0.5605 (3)	0.9574 (3)	1.0923 (2)	0.0389 (8)
H2	0.4809	0.9792	1.1146	0.047*
C3	0.5793 (4)	0.8189 (4)	1.1003 (2)	0.0475 (9)
H3A	0.6706	0.7999	1.1068	0.057*
H3B	0.5299	0.7897	1.1354	0.057*
C4	0.5312 (6)	0.7607 (4)	1.0422 (2)	0.0686 (14)
H4A	0.6014	0.7163	1.0224	0.082*
H4B	0.4615	0.7037	1.0514	0.082*
C5	0.6692 (3)	1.0458 (3)	1.11486 (17)	0.0362 (8)
C6	0.6657 (3)	1.0607 (4)	1.18514 (18)	0.0426 (9)
C7	0.6340 (5)	0.9655 (5)	1.2246 (2)	0.0617 (12)
H7	0.6143	0.8890	1.2085	0.074*
C8	0.6316 (6)	0.9834 (6)	1.2875 (2)	0.0774 (16)
H8	0.6084	0.9190	1.3131	0.093*
C9	0.6623 (6)	1.0930 (6)	1.3127 (2)	0.0794 (17)
H9	0.6607	1.1041	1.3551	0.095*
C10	0.6950 (7)	1.1847 (6)	1.2750 (2)	0.0826 (17)
H10	0.7169	1.2597	1.2921	0.099*
C11	0.6975 (5)	1.1726 (4)	1.2122 (2)	0.0611 (11)
H11	0.7202	1.2388	1.1877	0.073*
C12	0.8038 (4)	0.9953 (3)	1.0934 (2)	0.0411 (8)
C13	0.6455 (3)	1.1693 (3)	1.08343 (16)	0.0351 (7)
C14	0.7313 (4)	1.2233 (4)	1.04213 (18)	0.0448 (9)
H14	0.8116	1.1868	1.0346	0.054*
C15	0.6995 (5)	1.3297 (4)	1.0122 (2)	0.0540 (10)
H15	0.7576	1.3626	0.9838	0.065*
C16	0.5835 (4)	1.3883 (4)	1.0233 (2)	0.0539 (10)
H16	0.5631	1.4611	1.0034	0.065*
C17	0.4976 (4)	1.3360 (4)	1.06486 (19)	0.0516 (10)
H17	0.4181	1.3738	1.0727	0.062*
C18	0.5280 (4)	1.2300 (4)	1.0944 (2)	0.0476 (9)
H18	0.4693	1.1974	1.1225	0.057*
C19	0.4492 (5)	0.8315 (4)	0.94064 (19)	0.0540 (10)
H19A	0.3583	0.8072	0.9412	0.065*
H19B	0.4983	0.7606	0.9274	0.065*
C20A	0.4620 (17)	0.9225 (13)	0.8917 (6)	0.061 (4)	0.34
H20A	0.5507	0.9234	0.8762	0.073*	0.34
H20B	0.4417	1.0031	0.9075	0.073*	0.34
C20B	0.3745 (7)	0.9232 (6)	0.9058 (3)	0.0522 (15)	0.66
H20C	0.4175	1.0019	0.9090	0.063*	0.66
H20D	0.2882	0.9310	0.9235	0.063*	0.66
C21	0.3624 (6)	0.8874 (5)	0.8370 (2)	0.0757 (15)
C22	0.2571 (6)	0.9394 (5)	0.8092 (3)	0.0838 (19)
H22	0.2082	0.9963	0.8310	0.101*
C23	0.2203 (7)	0.9105 (5)	0.7496 (3)	0.0851 (17)
H23	0.1490	0.9477	0.7310	0.102*
C24	0.2931 (6)	0.8250 (5)	0.7192 (2)	0.0676 (13)
C25	0.3778 (7)	0.7098 (8)	0.6432 (3)	0.101 (2)
H25A	0.4329	0.7537	0.6145	0.121*
H25B	0.3474	0.6358	0.6233	0.121*
C26	0.4540 (6)	0.6781 (7)	0.7004 (3)	0.0924 (19)
H26A	0.5470	0.6875	0.6941	0.111*
H26B	0.4357	0.5956	0.7142	0.111*
C27	0.4011 (5)	0.7728 (5)	0.7451 (2)	0.0620 (12)
C28	0.4357 (6)	0.8019 (5)	0.8044 (2)	0.0731 (15)
H28	0.5075	0.7649	0.8227	0.088*

	U11	U22	U33	U12	U13	U23
Br1	0.04001 (18)	0.1050 (4)	0.0736 (3)	−0.0003 (3)	−0.0002 (2)	0.0401 (3)
O1	0.0539 (18)	0.0521 (17)	0.0601 (18)	0.0106 (14)	0.0124 (14)	−0.0081 (14)
O2	0.105 (3)	0.098 (3)	0.065 (2)	−0.006 (3)	−0.041 (2)	−0.005 (2)
N1	0.133 (4)	0.044 (2)	0.062 (2)	−0.029 (2)	−0.040 (3)	0.0073 (18)
N2	0.0346 (19)	0.075 (3)	0.070 (3)	0.0114 (19)	0.0007 (18)	−0.004 (2)
C1	0.049 (2)	0.0344 (19)	0.045 (2)	−0.0030 (16)	−0.0053 (17)	−0.0020 (16)
C2	0.0372 (17)	0.0395 (19)	0.0400 (19)	−0.0023 (15)	0.0002 (17)	0.0062 (17)
C3	0.055 (2)	0.042 (2)	0.046 (2)	−0.0027 (18)	0.0002 (19)	0.0074 (18)
C4	0.108 (4)	0.039 (2)	0.058 (3)	0.012 (3)	−0.013 (3)	0.001 (2)
C5	0.0321 (17)	0.0388 (19)	0.0378 (19)	−0.0017 (14)	0.0028 (13)	−0.0005 (15)
C6	0.0356 (18)	0.051 (2)	0.041 (2)	0.0044 (16)	−0.0004 (15)	0.0007 (17)
C7	0.087 (3)	0.060 (3)	0.039 (2)	−0.002 (3)	0.003 (2)	0.001 (2)
C8	0.113 (4)	0.081 (4)	0.039 (3)	0.012 (3)	−0.002 (3)	0.009 (3)
C9	0.095 (4)	0.106 (5)	0.037 (2)	0.033 (3)	−0.006 (2)	−0.015 (3)
C10	0.098 (4)	0.094 (4)	0.056 (3)	0.018 (4)	−0.023 (3)	−0.036 (3)
C11	0.071 (3)	0.060 (3)	0.053 (3)	−0.006 (3)	−0.007 (2)	−0.005 (2)
C12	0.0372 (17)	0.0320 (17)	0.054 (2)	0.0011 (15)	0.008 (2)	0.0026 (17)
C13	0.0376 (16)	0.0329 (17)	0.0347 (18)	−0.0025 (13)	−0.0019 (14)	−0.0049 (15)
C14	0.039 (2)	0.041 (2)	0.054 (2)	−0.0039 (16)	0.0063 (17)	−0.0055 (17)
C15	0.061 (2)	0.042 (2)	0.059 (2)	−0.013 (2)	0.003 (2)	0.0085 (18)
C16	0.071 (3)	0.038 (2)	0.052 (2)	0.002 (2)	−0.014 (2)	−0.003 (2)
C17	0.059 (2)	0.046 (2)	0.050 (2)	0.0158 (19)	−0.0084 (19)	−0.0079 (18)
C18	0.0421 (19)	0.055 (2)	0.046 (2)	0.0082 (17)	0.0016 (18)	0.000 (2)
C19	0.070 (3)	0.041 (2)	0.051 (2)	0.002 (2)	−0.012 (2)	−0.0066 (19)
C20A	0.071 (9)	0.058 (8)	0.053 (8)	−0.014 (7)	−0.012 (7)	0.015 (6)
C20B	0.058 (4)	0.041 (3)	0.058 (4)	0.005 (3)	−0.009 (4)	0.003 (3)
C21	0.123 (4)	0.049 (3)	0.055 (3)	−0.007 (3)	−0.026 (3)	0.006 (2)
C22	0.114 (5)	0.067 (3)	0.071 (4)	0.021 (3)	−0.013 (3)	0.000 (3)
C23	0.094 (4)	0.071 (4)	0.090 (4)	0.016 (3)	−0.038 (4)	−0.009 (3)
C24	0.077 (3)	0.068 (3)	0.058 (3)	−0.010 (3)	−0.026 (3)	0.012 (2)
C25	0.098 (5)	0.141 (7)	0.063 (4)	−0.020 (5)	−0.001 (3)	−0.021 (4)
C26	0.079 (4)	0.105 (5)	0.093 (4)	0.002 (3)	−0.018 (3)	−0.022 (4)
C27	0.061 (3)	0.070 (3)	0.055 (3)	−0.013 (2)	−0.017 (2)	0.002 (2)
C28	0.084 (4)	0.066 (3)	0.070 (3)	0.004 (3)	−0.037 (3)	0.005 (3)

O1—C12	1.222 (5)	C13—C18	1.397 (5)
O2—C24	1.378 (6)	C14—C15	1.374 (6)
O2—C25	1.420 (8)	C14—H14	0.9300
N1—C4	1.406 (6)	C15—C16	1.375 (7)
N1—C19	1.434 (5)	C15—H15	0.9300
N1—C1	1.446 (5)	C16—C17	1.387 (6)
N1—H1	0.9100	C16—H16	0.9300
N2—C12	1.324 (6)	C17—C18	1.363 (6)
N2—H2NA	0.863 (10)	C17—H17	0.9300
N2—H2NB	0.860 (10)	C18—H18	0.9300
C1—C2	1.530 (6)	C19—C20A	1.464 (13)
C1—H1A	0.9700	C19—C20B	1.473 (7)
C1—H1B	0.9700	C19—H19A	0.9700
C2—C3	1.539 (5)	C19—H19B	0.9700
C2—C5	1.557 (5)	C20A—C21	1.614 (14)
C2—H2	0.9800	C20A—H20A	0.9700
C3—C4	1.499 (6)	C20A—H20B	0.9700
C3—H3A	0.9700	C20B—C21	1.551 (9)
C3—H3B	0.9700	C20B—H20C	0.9700
C4—H4A	0.9700	C20B—H20D	0.9700
C4—H4B	0.9700	C21—C22	1.363 (8)
C5—C13	1.535 (5)	C21—C28	1.395 (8)
C5—C6	1.537 (5)	C22—C23	1.388 (8)
C5—C12	1.561 (5)	C22—H22	0.9300
C6—C7	1.389 (6)	C23—C24	1.368 (8)
C6—C11	1.398 (6)	C23—H23	0.9300
C7—C8	1.381 (7)	C24—C27	1.368 (7)
C7—H7	0.9300	C25—C26	1.511 (8)
C8—C9	1.357 (8)	C25—H25A	0.9700
C8—H8	0.9300	C25—H25B	0.9700
C9—C10	1.338 (8)	C26—C27	1.522 (8)
C9—H9	0.9300	C26—H26A	0.9700
C10—C11	1.372 (6)	C26—H26B	0.9700
C10—H10	0.9300	C27—C28	1.375 (7)
C11—H11	0.9300	C28—H28	0.9300
C13—C14	1.390 (5)
C24—O2—C25	107.4 (4)	C14—C15—C16	121.3 (4)
C4—N1—C19	122.4 (4)	C14—C15—H15	119.4
C4—N1—C1	111.0 (4)	C16—C15—H15	119.4
C19—N1—C1	121.8 (4)	C15—C16—C17	118.2 (4)
C4—N1—H1	97.3	C15—C16—H16	120.9
C19—N1—H1	97.3	C17—C16—H16	120.9
C1—N1—H1	97.3	C18—C17—C16	120.9 (4)
C12—N2—H2NA	123 (4)	C18—C17—H17	119.6
C12—N2—H2NB	122 (4)	C16—C17—H17	119.6
H2NA—N2—H2NB	114 (6)	C17—C18—C13	121.5 (4)
N1—C1—C2	105.6 (3)	C17—C18—H18	119.2
N1—C1—H1A	110.6	C13—C18—H18	119.2
C2—C1—H1A	110.6	N1—C19—C20A	123.5 (6)
N1—C1—H1B	110.6	N1—C19—C20B	120.5 (4)
C2—C1—H1B	110.6	C20A—C19—C20B	37.7 (7)
H1A—C1—H1B	108.7	N1—C19—H19A	106.4
C1—C2—C3	103.9 (3)	C20A—C19—H19A	106.4
C1—C2—C5	112.8 (3)	C20B—C19—H19A	72.2
C3—C2—C5	119.1 (3)	N1—C19—H19B	106.4
C1—C2—H2	106.8	C20A—C19—H19B	106.4
C3—C2—H2	106.8	C20B—C19—H19B	131.6
C5—C2—H2	106.8	H19A—C19—H19B	106.5
C4—C3—C2	106.4 (4)	C19—C20A—C21	108.4 (9)
C4—C3—H3A	110.5	C19—C20A—H20A	110.0
C2—C3—H3A	110.5	C21—C20A—H20A	110.0
C4—C3—H3B	110.5	C19—C20A—H20B	110.0
C2—C3—H3B	110.5	C21—C20A—H20B	110.0
H3A—C3—H3B	108.6	H20A—C20A—H20B	108.4
N1—C4—C3	108.0 (4)	C19—C20B—C21	111.4 (5)
N1—C4—H4A	110.1	C19—C20B—H20C	109.3
C3—C4—H4A	110.1	C21—C20B—H20C	109.3
N1—C4—H4B	110.1	C19—C20B—H20D	109.3
C3—C4—H4B	110.1	C21—C20B—H20D	109.3
H4A—C4—H4B	108.4	H20C—C20B—H20D	108.0
C13—C5—C6	110.2 (3)	C22—C21—C28	118.9 (5)
C13—C5—C2	107.1 (3)	C22—C21—C20B	112.6 (6)
C6—C5—C2	111.3 (3)	C28—C21—C20B	128.1 (5)
C13—C5—C12	108.6 (3)	C22—C21—C20A	136.8 (8)
C6—C5—C12	110.8 (3)	C28—C21—C20A	101.1 (8)
C2—C5—C12	108.6 (3)	C20B—C21—C20A	34.8 (6)
C7—C6—C11	116.9 (4)	C21—C22—C23	122.3 (6)
C7—C6—C5	122.7 (4)	C21—C22—H22	118.8
C11—C6—C5	120.4 (4)	C23—C22—H22	118.8
C8—C7—C6	120.6 (5)	C24—C23—C22	117.3 (5)
C8—C7—H7	119.7	C24—C23—H23	121.3
C6—C7—H7	119.7	C22—C23—H23	121.3
C9—C8—C7	121.5 (5)	C23—C24—C27	122.0 (5)
C9—C8—H8	119.3	C23—C24—O2	125.4 (5)
C7—C8—H8	119.3	C27—C24—O2	112.6 (5)
C10—C9—C8	118.3 (5)	O2—C25—C26	108.4 (5)
C10—C9—H9	120.8	O2—C25—H25A	110.0
C8—C9—H9	120.8	C26—C25—H25A	110.0
C9—C10—C11	122.8 (5)	O2—C25—H25B	110.0
C9—C10—H10	118.6	C26—C25—H25B	110.0
C11—C10—H10	118.6	H25A—C25—H25B	108.4
C10—C11—C6	120.0 (5)	C25—C26—C27	100.7 (5)
C10—C11—H11	120.0	C25—C26—H26A	111.6
C6—C11—H11	120.0	C27—C26—H26A	111.6
O1—C12—N2	122.4 (4)	C25—C26—H26B	111.6
O1—C12—C5	120.1 (4)	C27—C26—H26B	111.6
N2—C12—C5	117.6 (3)	H26A—C26—H26B	109.4
C14—C13—C18	117.1 (3)	C24—C27—C28	119.9 (5)
C14—C13—C5	124.2 (3)	C24—C27—C26	108.1 (4)
C18—C13—C5	118.7 (3)	C28—C27—C26	131.7 (5)
C15—C14—C13	121.1 (4)	C27—C28—C21	119.5 (5)
C15—C14—H14	119.5	C27—C28—H28	120.2
C13—C14—H14	119.5	C21—C28—H28	120.2
C4—N1—C1—C2	−23.2 (6)	C5—C13—C14—C15	175.0 (4)
C19—N1—C1—C2	−179.2 (5)	C13—C14—C15—C16	1.9 (6)
N1—C1—C2—C3	20.9 (4)	C14—C15—C16—C17	−1.2 (6)
N1—C1—C2—C5	151.3 (4)	C15—C16—C17—C18	0.7 (6)
C1—C2—C3—C4	−12.2 (5)	C16—C17—C18—C13	−0.8 (6)
C5—C2—C3—C4	−138.7 (4)	C14—C13—C18—C17	1.4 (6)
C19—N1—C4—C3	171.2 (5)	C5—C13—C18—C17	−175.7 (4)
C1—N1—C4—C3	15.3 (7)	C4—N1—C19—C20A	−149.3 (10)
C2—C3—C4—N1	−1.1 (6)	C1—N1—C19—C20A	4.0 (12)
C1—C2—C5—C13	40.3 (4)	C4—N1—C19—C20B	166.0 (6)
C3—C2—C5—C13	162.5 (4)	C1—N1—C19—C20B	−40.7 (8)
C1—C2—C5—C6	160.8 (3)	N1—C19—C20A—C21	−157.4 (7)
C3—C2—C5—C6	−77.0 (5)	C20B—C19—C20A—C21	−59.4 (9)
C1—C2—C5—C12	−76.9 (4)	N1—C19—C20B—C21	172.5 (5)
C3—C2—C5—C12	45.3 (5)	C20A—C19—C20B—C21	65.9 (11)
C13—C5—C6—C7	154.5 (4)	C19—C20B—C21—C22	156.0 (6)
C2—C5—C6—C7	35.8 (5)	C19—C20B—C21—C28	−16.8 (10)
C12—C5—C6—C7	−85.2 (5)	C19—C20B—C21—C20A	−62.4 (10)
C13—C5—C6—C11	−26.7 (5)	C19—C20A—C21—C22	118.0 (10)
C2—C5—C6—C11	−145.4 (4)	C19—C20A—C21—C28	−83.9 (11)
C12—C5—C6—C11	93.6 (4)	C19—C20A—C21—C20B	61.1 (9)
C11—C6—C7—C8	1.5 (7)	C28—C21—C22—C23	0.0 (9)
C5—C6—C7—C8	−179.7 (5)	C20B—C21—C22—C23	−173.6 (6)
C6—C7—C8—C9	−1.3 (9)	C20A—C21—C22—C23	155.2 (10)
C7—C8—C9—C10	0.2 (9)	C21—C22—C23—C24	1.0 (10)
C8—C9—C10—C11	0.6 (10)	C22—C23—C24—C27	−2.5 (9)
C9—C10—C11—C6	−0.4 (9)	C22—C23—C24—O2	178.9 (6)
C7—C6—C11—C10	−0.7 (7)	C25—O2—C24—C23	171.6 (6)
C5—C6—C11—C10	−179.5 (5)	C25—O2—C24—C27	−7.1 (7)
C13—C5—C12—O1	−77.7 (4)	C24—O2—C25—C26	15.4 (7)
C6—C5—C12—O1	161.0 (4)	O2—C25—C26—C27	−16.7 (7)
C2—C5—C12—O1	38.5 (5)	C23—C24—C27—C28	3.0 (8)
C13—C5—C12—N2	100.3 (4)	O2—C24—C27—C28	−178.2 (5)
C6—C5—C12—N2	−20.9 (5)	C23—C24—C27—C26	177.2 (6)
C2—C5—C12—N2	−143.5 (4)	O2—C24—C27—C26	−4.0 (6)
C6—C5—C13—C14	122.6 (4)	C25—C26—C27—C24	12.5 (6)
C2—C5—C13—C14	−116.2 (4)	C25—C26—C27—C28	−174.3 (6)
C12—C5—C13—C14	1.0 (5)	C24—C27—C28—C21	−1.9 (8)
C6—C5—C13—C18	−60.5 (4)	C26—C27—C28—C21	−174.5 (6)
C2—C5—C13—C18	60.8 (4)	C22—C21—C28—C27	0.5 (9)
C12—C5—C13—C18	177.9 (3)	C20B—C21—C28—C27	172.9 (6)
C18—C13—C14—C15	−2.0 (6)	C20A—C21—C28—C27	−162.5 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···Br1i	0.91	2.57	3.453 (6)	164
N2—H2NB···Br1ii	0.86 (1)	2.66 (1)	3.514 (4)	175 (5)
C18—H18···O2iii	0.93	2.60	3.382 (6)	142
C19—H19B···Br1iv	0.97	2.69	3.609 (5)	158
C4—H4A···Br1iv	0.97	2.92	3.770 (5)	147
C1—H1B···O1	0.97	2.37	2.959 (5)	119

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯Br1i	0.91	2.57	3.453 (6)	164
N2—H2NB⋯Br1ii	0.86 (1)	2.66 (1)	3.514 (4)	175 (5)
C18—H18⋯O2iii	0.93	2.60	3.382 (6)	142
C19—H19B⋯Br1iv	0.97	2.69	3.609 (5)	158
C4—H4A⋯Br1iv	0.97	2.92	3.770 (5)	147
C1—H1B⋯O1	0.97	2.37	2.959 (5)	119

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .