1-(4-tert-Butyl-benz-yl)-3-(3,4,5-tri-methoxy-benz-yl)benzimidazolium bromide monohydrate.

A novel N-heterocyclic carbene derivative, C(28)H(33)N(2)O(3) (+)·Br(-)·H(2)O, was synthesized and characterized by elemental analysis, (1)H and (13)C-NMR and IR spectroscopy and a single-crystal X-ray diffraction study. Ions of the title compound are linked by π⋯π stacking inter-actions (face-face separation 3.441 Å) and C-H⋯Br and O-H⋯Br inter-actions. Intra- and intermolecular C-H⋯O inter-actions are also present. The C-N bond lengths for the compound [1.329 (3), 1.325 (3), 1.389 (3) and 1.391 (3) Å] are all shorter than the average single C-N bond length of 1.48 Å, thus showing varying degrees of double-bond character.

Related literature

For the synthesis, see: Yaşar et al. (2008 ▶). For general background, see: Herrmann (2002 ▶); Arduengo & Krafczyc (1998 ▶); Herrmann et al. (1995 ▶, 1998 ▶); Navarro et al. (2006 ▶). For related compounds, see: Yaşar et al. (2008 ▶); Arslan et al. (2009 ▶ and references therein). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C28H33N2O3 +·Br−·H2O

M = 543.49

Triclinic,

a = 10.389 (2) Å

b = 10.436 (2) Å

c = 14.038 (3) Å

α = 109.79 (3)°

β = 90.70 (3)°

γ = 103.57 (3)°

V = 1385.1 (6) Å3

Z = 2

Mo Kα radiation

μ = 1.52 mm−1

T = 298 (2) K

0.48 × 0.29 × 0.26 mm

Data collection

Mercury CCD diffractometer

Absorption correction: multi-scan (REQAB; Jacobson, 1998 ▶) T min = 0.514, T max = 0.673

11938 measured reflections

4860 independent reflections

3921 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.112

S = 1.08

4860 reflections

328 parameters

2 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.55 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2001 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I. DOI: 10.1107/S1600536808043250/hg2459sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808043250/hg2459Isup2.hkl

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

C28H33N2O3+·Br−·H2O	Z = 2
Mr = 543.49	F(000) = 568
Triclinic, P1	Dx = 1.303 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.389 (2) Å	Cell parameters from 4659 reflections
b = 10.436 (2) Å	θ = 3.2–26.4°
c = 14.038 (3) Å	µ = 1.52 mm−1
α = 109.79 (3)°	T = 298 K
β = 90.70 (3)°	Rod, colorless
γ = 103.57 (3)°	0.48 × 0.29 × 0.26 mm
V = 1385.1 (6) Å3

Mercury CCD diffractometer	4860 independent reflections
Radiation source: Sealed Tube	3921 reflections with I > 2σ(I)
Graphite Monochromator	Rint = 0.022
Detector resolution: 14.6306 pixels mm-1	θmax = 25.0°, θmin = 3.2°
ω scans	h = −12→12
Absorption correction: multi-scan (REQAB; Jacobson, 1998)	k = −12→12
Tmin = 0.514, Tmax = 0.673	l = −16→16
11938 measured reflections

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.112	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0505P)2 + 0.6557P] where P = (Fo2 + 2Fc2)/3
4860 reflections	(Δ/σ)max = 0.001
328 parameters	Δρmax = 0.31 e Å−3
2 restraints	Δρmin = −0.55 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	0.75295 (3)	0.93707 (4)	0.51515 (3)	0.06917 (15)
N1	0.8315 (2)	0.5830 (2)	0.57685 (15)	0.0384 (5)
N2	1.0326 (2)	0.7189 (2)	0.62364 (16)	0.0407 (5)
C1	0.9118 (3)	0.7064 (3)	0.5843 (2)	0.0439 (6)
H1	0.8858	0.7766	0.5640	0.053*
C2	1.0322 (2)	0.5974 (2)	0.64403 (18)	0.0363 (5)
C3	1.1313 (3)	0.5558 (3)	0.6834 (2)	0.0497 (7)
H3	1.2196	0.6159	0.7050	0.060*
C4	1.0966 (3)	0.4233 (3)	0.6901 (2)	0.0609 (8)
H4	1.1626	0.3902	0.7168	0.073*
C5	0.9681 (3)	0.3364 (3)	0.6591 (2)	0.0573 (7)
H5	0.9483	0.2449	0.6650	0.069*
C6	0.8695 (3)	0.3772 (3)	0.6207 (2)	0.0449 (6)
H6	0.7811	0.3170	0.5997	0.054*
C7	0.9039 (2)	0.5104 (2)	0.61354 (18)	0.0351 (5)
C8	0.6876 (2)	0.5379 (3)	0.5428 (2)	0.0454 (6)
H8A	0.6617	0.4377	0.5084	0.054*
H8B	0.6699	0.5814	0.4955	0.054*
C9	0.6061 (2)	0.5776 (3)	0.6319 (2)	0.0438 (6)
C10	0.5443 (3)	0.4785 (3)	0.6729 (2)	0.0456 (6)
H10	0.5523	0.3835	0.6449	0.055*
C11	0.4705 (3)	0.5178 (3)	0.7550 (2)	0.0521 (7)
C12	0.4583 (3)	0.6547 (3)	0.7952 (2)	0.0537 (7)
C13	0.5222 (3)	0.7534 (3)	0.7543 (2)	0.0553 (7)
C14	0.5963 (3)	0.7155 (3)	0.6720 (2)	0.0508 (7)
H14	0.6399	0.7839	0.6435	0.061*
C15	0.4234 (4)	0.2906 (4)	0.7695 (3)	0.0873 (12)
H15A	0.3873	0.2414	0.6998	0.131*
H15B	0.3783	0.2416	0.8112	0.131*
H15C	0.5166	0.2951	0.7756	0.131*
C16	0.4304 (4)	0.7401 (6)	0.9699 (3)	0.1083 (17)
H16A	0.4738	0.6735	0.9805	0.162*
H16B	0.3620	0.7526	1.0150	0.162*
H16C	0.4944	0.8286	0.9835	0.162*
C17	0.5773 (7)	0.9936 (4)	0.7672 (4)	0.119 (2)
H17A	0.6705	0.9984	0.7736	0.179*
H17B	0.5622	1.0823	0.8082	0.179*
H17C	0.5478	0.9731	0.6973	0.179*
C18	1.1457 (3)	0.8450 (3)	0.6461 (2)	0.0536 (7)
H18A	1.1451	0.8826	0.5925	0.064*
H18B	1.2277	0.8182	0.6483	0.064*
C19	1.1387 (3)	0.9570 (3)	0.7460 (2)	0.0450 (6)
C20	1.0657 (4)	1.0516 (3)	0.7490 (2)	0.0671 (9)
H20	1.0205	1.0466	0.6873	0.081*
C21	1.0563 (4)	1.1546 (3)	0.8403 (2)	0.0677 (9)
H21	1.0048	1.2198	0.8403	0.081*
C22	1.1192 (3)	1.1659 (3)	0.9317 (2)	0.0452 (6)
C23	1.1931 (3)	1.0704 (3)	0.9268 (2)	0.0532 (7)
H23	1.2390	1.0752	0.9883	0.064*
C24	1.2033 (3)	0.9667 (3)	0.8350 (2)	0.0533 (7)
H24	1.2558	0.9019	0.8342	0.064*
C25	1.1111 (3)	1.2836 (3)	1.0308 (2)	0.0591 (8)
C26	0.9702 (4)	1.3046 (5)	1.0365 (3)	0.0903 (13)
H26A	0.9665	1.3779	1.0993	0.135*
H26B	0.9085	1.2186	1.0334	0.135*
H26C	0.9472	1.3306	0.9804	0.135*
C27	1.2089 (5)	1.4190 (4)	1.0328 (4)	0.1013 (15)
H27A	1.2976	1.4066	1.0315	0.152*
H27B	1.2037	1.4947	1.0937	0.152*
H27C	1.1868	1.4408	0.9745	0.152*
C28	1.1443 (4)	1.2485 (5)	1.1241 (3)	0.0840 (11)
H28A	1.2353	1.2435	1.1266	0.126*
H28B	1.0870	1.1594	1.1196	0.126*
H28C	1.1315	1.3204	1.1846	0.126*
O1	0.4055 (2)	0.4294 (3)	0.80195 (18)	0.0717 (6)
O2	0.3740 (2)	0.6898 (3)	0.86948 (17)	0.0741 (7)
O3	0.5058 (3)	0.8868 (3)	0.8002 (2)	0.0870 (8)
O4	0.5832 (3)	0.1696 (3)	0.4946 (3)	0.0969 (10)
H4A	0.499 (2)	0.144 (6)	0.501 (4)	0.145*
H4B	0.623 (5)	0.107 (5)	0.501 (4)	0.145*

	U11	U22	U33	U12	U13	U23
Br1	0.0556 (2)	0.0784 (2)	0.0980 (3)	0.02072 (16)	0.01227 (17)	0.0592 (2)
N1	0.0361 (11)	0.0451 (11)	0.0394 (12)	0.0158 (9)	0.0067 (9)	0.0176 (9)
N2	0.0412 (12)	0.0386 (11)	0.0437 (12)	0.0106 (9)	0.0121 (9)	0.0156 (9)
C1	0.0482 (15)	0.0452 (14)	0.0470 (15)	0.0210 (12)	0.0139 (12)	0.0208 (12)
C2	0.0364 (12)	0.0393 (12)	0.0342 (13)	0.0132 (10)	0.0078 (10)	0.0117 (10)
C3	0.0378 (14)	0.0634 (17)	0.0469 (16)	0.0149 (13)	0.0004 (12)	0.0169 (13)
C4	0.0558 (18)	0.073 (2)	0.067 (2)	0.0308 (16)	−0.0007 (15)	0.0315 (16)
C5	0.067 (2)	0.0494 (16)	0.0648 (19)	0.0205 (15)	0.0037 (15)	0.0284 (14)
C6	0.0463 (15)	0.0391 (13)	0.0477 (15)	0.0082 (11)	0.0045 (12)	0.0148 (11)
C7	0.0348 (12)	0.0396 (12)	0.0330 (12)	0.0147 (10)	0.0060 (10)	0.0119 (10)
C8	0.0360 (13)	0.0599 (16)	0.0433 (15)	0.0190 (12)	0.0027 (11)	0.0173 (12)
C9	0.0329 (13)	0.0567 (15)	0.0432 (14)	0.0176 (12)	0.0004 (11)	0.0155 (12)
C10	0.0366 (13)	0.0535 (15)	0.0483 (16)	0.0120 (12)	0.0020 (11)	0.0195 (12)
C11	0.0363 (14)	0.0673 (18)	0.0546 (17)	0.0098 (13)	0.0039 (12)	0.0260 (14)
C12	0.0355 (14)	0.079 (2)	0.0471 (16)	0.0209 (14)	0.0077 (12)	0.0187 (14)
C13	0.0541 (17)	0.0633 (18)	0.0550 (17)	0.0314 (15)	0.0114 (14)	0.0175 (14)
C14	0.0493 (16)	0.0589 (17)	0.0537 (17)	0.0222 (13)	0.0107 (13)	0.0260 (13)
C15	0.091 (3)	0.081 (3)	0.099 (3)	0.006 (2)	0.019 (2)	0.054 (2)
C16	0.078 (3)	0.170 (5)	0.054 (2)	0.022 (3)	0.013 (2)	0.016 (3)
C17	0.195 (6)	0.063 (2)	0.112 (4)	0.055 (3)	0.059 (4)	0.030 (2)
C18	0.0514 (16)	0.0446 (15)	0.0592 (18)	0.0025 (12)	0.0187 (14)	0.0175 (13)
C19	0.0452 (14)	0.0382 (13)	0.0515 (16)	0.0060 (11)	0.0132 (12)	0.0184 (11)
C20	0.097 (3)	0.0610 (19)	0.0488 (18)	0.0340 (18)	−0.0027 (17)	0.0174 (14)
C21	0.097 (3)	0.0613 (19)	0.0550 (19)	0.0438 (19)	0.0010 (18)	0.0179 (15)
C22	0.0462 (15)	0.0448 (14)	0.0458 (15)	0.0110 (12)	0.0085 (12)	0.0176 (12)
C23	0.0498 (16)	0.0567 (17)	0.0518 (17)	0.0147 (13)	−0.0032 (13)	0.0170 (13)
C24	0.0456 (15)	0.0498 (15)	0.0653 (19)	0.0185 (13)	0.0051 (14)	0.0170 (14)
C25	0.0622 (19)	0.0573 (17)	0.0523 (18)	0.0180 (15)	0.0122 (15)	0.0103 (14)
C26	0.091 (3)	0.113 (3)	0.072 (3)	0.056 (3)	0.024 (2)	0.018 (2)
C27	0.127 (4)	0.053 (2)	0.093 (3)	0.002 (2)	0.024 (3)	0.000 (2)
C28	0.087 (3)	0.112 (3)	0.0454 (19)	0.032 (2)	0.0076 (18)	0.0146 (19)
O1	0.0604 (14)	0.0848 (16)	0.0758 (16)	0.0089 (12)	0.0203 (12)	0.0416 (13)
O2	0.0492 (12)	0.1158 (19)	0.0554 (14)	0.0316 (13)	0.0177 (10)	0.0202 (13)
O3	0.111 (2)	0.0785 (16)	0.0900 (19)	0.0592 (16)	0.0421 (16)	0.0286 (14)
O4	0.0533 (14)	0.0568 (14)	0.174 (3)	0.0082 (12)	−0.0014 (18)	0.0367 (17)

N1—C1	1.329 (3)	C16—H16A	0.9599
N1—C7	1.389 (3)	C16—H16B	0.9599
N1—C8	1.478 (3)	C16—H16C	0.9599
N2—C1	1.325 (3)	C17—O3	1.407 (5)
N2—C2	1.391 (3)	C17—H17A	0.9599
N2—C18	1.481 (3)	C17—H17B	0.9599
C1—H1	0.9600	C17—H17C	0.9599
C2—C3	1.382 (4)	C18—C19	1.507 (4)
C2—C7	1.393 (3)	C18—H18A	0.9600
C3—C4	1.380 (4)	C18—H18B	0.9600
C3—H3	0.9600	C19—C20	1.370 (4)
C4—C5	1.394 (5)	C19—C24	1.372 (4)
C4—H4	0.9600	C20—C21	1.389 (4)
C5—C6	1.368 (4)	C20—H20	0.9600
C5—H5	0.9600	C21—C22	1.388 (4)
C6—C7	1.390 (3)	C21—H21	0.9600
C6—H6	0.9600	C22—C23	1.380 (4)
C8—C9	1.513 (4)	C22—C25	1.532 (4)
C8—H8A	0.9600	C23—C24	1.399 (4)
C8—H8B	0.9600	C23—H23	0.9600
C9—C10	1.383 (4)	C24—H24	0.9600
C9—C14	1.386 (4)	C25—C27	1.526 (5)
C10—C11	1.390 (4)	C25—C26	1.529 (5)
C10—H10	0.9600	C25—C28	1.530 (5)
C11—O1	1.369 (3)	C26—H26A	0.9599
C11—C12	1.385 (4)	C26—H26B	0.9599
C12—O2	1.380 (3)	C26—H26C	0.9599
C12—C13	1.385 (4)	C27—H27A	0.9599
C13—O3	1.374 (4)	C27—H27B	0.9599
C13—C14	1.392 (4)	C27—H27C	0.9599
C14—H14	0.9600	C28—H28A	0.9599
C15—O1	1.422 (5)	C28—H28B	0.9599
C15—H15A	0.9599	C28—H28C	0.9599
C15—H15B	0.9599	O4—H4A	0.87 (2)
C15—H15C	0.9599	O4—H4B	0.88 (5)
C16—O2	1.394 (5)
C1—N1—C7	108.2 (2)	H16A—C16—H16C	109.5
C1—N1—C8	125.0 (2)	H16B—C16—H16C	109.5
C7—N1—C8	126.6 (2)	O3—C17—H17A	109.5
C1—N2—C2	108.4 (2)	O3—C17—H17B	109.5
C1—N2—C18	124.9 (2)	H17A—C17—H17B	109.5
C2—N2—C18	126.6 (2)	O3—C17—H17C	109.5
N2—C1—N1	110.5 (2)	H17A—C17—H17C	109.5
N2—C1—H1	124.8	H17B—C17—H17C	109.5
N1—C1—H1	124.8	N2—C18—C19	111.7 (2)
C3—C2—N2	132.0 (2)	N2—C18—H18A	109.3
C3—C2—C7	121.6 (2)	C19—C18—H18A	109.3
N2—C2—C7	106.3 (2)	N2—C18—H18B	109.3
C4—C3—C2	116.5 (3)	C19—C18—H18B	109.3
C4—C3—H3	121.7	H18A—C18—H18B	107.9
C2—C3—H3	121.7	C20—C19—C24	118.7 (3)
C3—C4—C5	121.6 (3)	C20—C19—C18	119.6 (3)
C3—C4—H4	119.2	C24—C19—C18	121.7 (3)
C5—C4—H4	119.2	C19—C20—C21	120.7 (3)
C6—C5—C4	122.1 (3)	C19—C20—H20	119.7
C6—C5—H5	118.9	C21—C20—H20	119.7
C4—C5—H5	118.9	C22—C21—C20	121.9 (3)
C5—C6—C7	116.5 (3)	C22—C21—H21	119.1
C5—C6—H6	121.8	C20—C21—H21	119.1
C7—C6—H6	121.8	C23—C22—C21	116.4 (3)
N1—C7—C6	131.8 (2)	C23—C22—C25	122.7 (3)
N1—C7—C2	106.6 (2)	C21—C22—C25	120.8 (3)
C6—C7—C2	121.6 (2)	C22—C23—C24	121.9 (3)
N1—C8—C9	111.2 (2)	C22—C23—H23	119.1
N1—C8—H8A	109.4	C24—C23—H23	119.1
C9—C8—H8A	109.4	C19—C24—C23	120.4 (3)
N1—C8—H8B	109.4	C19—C24—H24	119.8
C9—C8—H8B	109.4	C23—C24—H24	119.8
H8A—C8—H8B	108.0	C27—C25—C26	109.6 (3)
C10—C9—C14	120.8 (2)	C27—C25—C28	110.0 (3)
C10—C9—C8	120.6 (2)	C26—C25—C28	107.1 (3)
C14—C9—C8	118.6 (2)	C27—C25—C22	108.2 (3)
C9—C10—C11	119.5 (3)	C26—C25—C22	110.5 (3)
C9—C10—H10	120.3	C28—C25—C22	111.5 (3)
C11—C10—H10	120.3	C25—C26—H26A	109.5
O1—C11—C12	114.9 (3)	C25—C26—H26B	109.5
O1—C11—C10	124.7 (3)	H26A—C26—H26B	109.5
C12—C11—C10	120.4 (3)	C25—C26—H26C	109.5
O2—C12—C11	120.2 (3)	H26A—C26—H26C	109.5
O2—C12—C13	120.0 (3)	H26B—C26—H26C	109.5
C11—C12—C13	119.6 (3)	C25—C27—H27A	109.5
O3—C13—C12	115.3 (3)	C25—C27—H27B	109.5
O3—C13—C14	124.1 (3)	H27A—C27—H27B	109.5
C12—C13—C14	120.6 (3)	C25—C27—H27C	109.5
C9—C14—C13	119.1 (3)	H27A—C27—H27C	109.5
C9—C14—H14	120.5	H27B—C27—H27C	109.5
C13—C14—H14	120.5	C25—C28—H28A	109.5
O1—C15—H15A	109.5	C25—C28—H28B	109.5
O1—C15—H15B	109.5	H28A—C28—H28B	109.5
H15A—C15—H15B	109.5	C25—C28—H28C	109.5
O1—C15—H15C	109.5	H28A—C28—H28C	109.5
H15A—C15—H15C	109.5	H28B—C28—H28C	109.5
H15B—C15—H15C	109.5	C11—O1—C15	117.4 (3)
O2—C16—H16A	109.5	C12—O2—C16	116.4 (3)
O2—C16—H16B	109.5	C13—O3—C17	117.6 (3)
H16A—C16—H16B	109.5	H4A—O4—H4B	110 (5)
O2—C16—H16C	109.5
C2—N2—C1—N1	−0.4 (3)	O2—C12—C13—O3	6.4 (4)
C18—N2—C1—N1	−177.7 (2)	C11—C12—C13—O3	−179.1 (3)
C7—N1—C1—N2	0.1 (3)	O2—C12—C13—C14	−173.2 (3)
C8—N1—C1—N2	175.6 (2)	C11—C12—C13—C14	1.4 (5)
C1—N2—C2—C3	179.0 (3)	C10—C9—C14—C13	−0.4 (4)
C18—N2—C2—C3	−3.8 (4)	C8—C9—C14—C13	−179.7 (3)
C1—N2—C2—C7	0.6 (3)	O3—C13—C14—C9	179.9 (3)
C18—N2—C2—C7	177.8 (2)	C12—C13—C14—C9	−0.5 (4)
N2—C2—C3—C4	−177.6 (3)	C1—N2—C18—C19	81.3 (3)
C7—C2—C3—C4	0.5 (4)	C2—N2—C18—C19	−95.5 (3)
C2—C3—C4—C5	−0.3 (4)	N2—C18—C19—C20	−86.2 (3)
C3—C4—C5—C6	−0.1 (5)	N2—C18—C19—C24	93.5 (3)
C4—C5—C6—C7	0.2 (4)	C24—C19—C20—C21	−0.5 (5)
C1—N1—C7—C6	−178.2 (3)	C18—C19—C20—C21	179.1 (3)
C8—N1—C7—C6	6.3 (4)	C19—C20—C21—C22	−0.3 (6)
C1—N1—C7—C2	0.3 (3)	C20—C21—C22—C23	0.8 (5)
C8—N1—C7—C2	−175.2 (2)	C20—C21—C22—C25	177.9 (3)
C5—C6—C7—N1	178.4 (3)	C21—C22—C23—C24	−0.6 (4)
C5—C6—C7—C2	0.0 (4)	C25—C22—C23—C24	−177.7 (3)
C3—C2—C7—N1	−179.1 (2)	C20—C19—C24—C23	0.7 (4)
N2—C2—C7—N1	−0.5 (2)	C18—C19—C24—C23	−178.9 (3)
C3—C2—C7—C6	−0.4 (4)	C22—C23—C24—C19	−0.1 (4)
N2—C2—C7—C6	178.2 (2)	C23—C22—C25—C27	98.5 (4)
C1—N1—C8—C9	−90.8 (3)	C21—C22—C25—C27	−78.4 (4)
C7—N1—C8—C9	84.0 (3)	C23—C22—C25—C26	−141.5 (3)
N1—C8—C9—C10	−100.3 (3)	C21—C22—C25—C26	41.6 (4)
N1—C8—C9—C14	78.9 (3)	C23—C22—C25—C28	−22.5 (4)
C14—C9—C10—C11	0.5 (4)	C21—C22—C25—C28	160.6 (3)
C8—C9—C10—C11	179.7 (2)	C12—C11—O1—C15	−175.0 (3)
C9—C10—C11—O1	−179.8 (3)	C10—C11—O1—C15	5.2 (5)
C9—C10—C11—C12	0.3 (4)	C11—C12—O2—C16	92.8 (4)
O1—C11—C12—O2	−6.6 (4)	C13—C12—O2—C16	−92.7 (4)
C10—C11—C12—O2	173.3 (3)	C12—C13—O3—C17	175.0 (4)
O1—C11—C12—C13	178.9 (3)	C14—C13—O3—C17	−5.5 (6)
C10—C11—C12—C13	−1.2 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···Br1i	0.87 (3)	2.54 (3)	3.393 (3)	169 (5)
O4—H4B···Br1ii	0.88 (5)	2.52 (5)	3.399 (3)	176 (5)
C1—H1···Br1	0.96	2.65	3.587 (3)	165
C3—H3···O2iii	0.96	2.57	3.294 (4)	132
C6—H6···O4	0.96	2.38	3.305 (5)	161
C10—H10···O4	0.96	2.59	3.463 (5)	152
C14—H14···Br1	0.96	2.88	3.823 (3)	167
C18—H18A···Br1iv	0.96	2.82	3.718 (3)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H4A⋯Br1i	0.87 (3)	2.54 (3)	3.393 (3)	169 (5)
O4—H4B⋯Br1ii	0.88 (5)	2.52 (5)	3.399 (3)	176 (5)
C1—H1⋯Br1	0.96	2.65	3.587 (3)	165
C3—H3⋯O2iii	0.96	2.57	3.294 (4)	132
C6—H6⋯O4	0.96	2.38	3.305 (5)	161
C10—H10⋯O4	0.96	2.59	3.463 (5)	152
C14—H14⋯Br1	0.96	2.88	3.823 (3)	167
C18—H18A⋯Br1iv	0.96	2.82	3.718 (3)	155

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