Hexane-1,6-diaminium bis-[3,4,5,6-tetra-bromo-2-(meth-oxy-carbon-yl)benzoate] methanol disolvate.

In the title compound, C(6)H(18)N(2) (2+)·2C(9)H(3)Br(4)O(4) (-)·2CH(4)O, the carboxyl-ate and meth-oxy-carbonyl groups in one of the anions form dihedral angles of 71.9 (3) and 60.7 (3)°, respectively, with the aromatic ring while in the other anion these angles are 68.4 (3) and 56.8 (3)°, respectively. In the crystal, the constituent units are linked into a two-dimensional network parallel to the ab plane by N-H⋯O and O-H⋯O hydrogen bonds.

Related literature

For related structures, see: Li (2011a ▶,b ▶,c ▶).

Experimental

Crystal data

C6H18N2 2+·2C9H3Br4O4 −·2CH4O

M = 1171.74

Triclinic,

a = 8.1030 (6) Å

b = 13.5209 (12) Å

c = 17.7536 (17) Å

α = 89.388 (2)°

β = 83.744 (1)°

γ = 88.210 (2)°

V = 1932.5 (3) Å3

Z = 2

Mo Kα radiation

μ = 8.35 mm−1

T = 298 K

0.27 × 0.26 × 0.25 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1997 ▶) T min = 0.211, T max = 0.229

10205 measured reflections

6753 independent reflections

2917 reflections with I > 2σ(I)

R int = 0.072

Refinement

R[F 2 > 2σ(F 2)] = 0.067

wR(F 2) = 0.158

S = 1.04

6753 reflections

421 parameters

H-atom parameters constrained

Δρmax = 0.98 e Å−3

Δρmin = −0.91 e Å−3

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

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811035537/ci5198sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811035537/ci5198Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811035537/ci5198Isup3.cml

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

C6H18N22+·2C9H3Br4O4−·2CH4O	Z = 2
Mr = 1171.74	F(000) = 1124
Triclinic, P1	Dx = 2.014 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1030 (6) Å	Cell parameters from 2038 reflections
b = 13.5209 (12) Å	θ = 2.3–22.4°
c = 17.7536 (17) Å	µ = 8.35 mm−1
α = 89.388 (2)°	T = 298 K
β = 83.744 (1)°	Block, colourless
γ = 88.210 (2)°	0.27 × 0.26 × 0.25 mm
V = 1932.5 (3) Å3

Bruker SMART CCD area-detector diffractometer	6753 independent reflections
Radiation source: fine-focus sealed tube	2917 reflections with I > 2σ(I)
graphite	Rint = 0.072
φ and ω scans	θmax = 25.0°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Bruker, 1997)	h = −9→9
Tmin = 0.211, Tmax = 0.229	k = −14→16
10205 measured reflections	l = −21→18

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)] = 0.067	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.158	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0483P)2] where P = (Fo2 + 2Fc2)/3
6753 reflections	(Δ/σ)max = 0.001
421 parameters	Δρmax = 0.98 e Å−3
0 restraints	Δρmin = −0.91 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	0.31418 (12)	0.68365 (7)	0.41728 (5)	0.0652 (3)
Br2	0.39769 (12)	0.92318 (6)	0.39517 (6)	0.0725 (3)
Br3	0.56132 (12)	1.00591 (6)	0.22691 (6)	0.0648 (3)
Br4	0.66925 (12)	0.84716 (6)	0.08825 (5)	0.0645 (3)
Br5	1.15592 (12)	0.85386 (7)	0.58275 (5)	0.0659 (3)
Br6	1.09419 (14)	1.09575 (7)	0.60733 (6)	0.0837 (4)
Br7	0.94500 (13)	1.18227 (6)	0.77544 (7)	0.0795 (4)
Br8	0.83327 (14)	1.02581 (7)	0.91531 (6)	0.0863 (4)
N1	0.8619 (7)	0.5131 (4)	0.2862 (4)	0.051 (2)
H1A	0.9149	0.4572	0.2974	0.077*
H1B	0.9019	0.5339	0.2403	0.077*
H1C	0.7540	0.5024	0.2869	0.077*
N2	0.6252 (7)	0.6898 (4)	0.7155 (3)	0.048 (2)
H2A	0.6007	0.6274	0.7072	0.073*
H2B	0.5777	0.7084	0.7609	0.073*
H2C	0.7349	0.6946	0.7138	0.073*
O1	0.6599 (6)	0.5577 (4)	0.1436 (3)	0.0552 (17)
O2	0.4895 (8)	0.6342 (4)	0.0704 (3)	0.070 (2)
O3	0.2985 (7)	0.5302 (4)	0.2362 (4)	0.070 (2)
O4	0.5040 (6)	0.5022 (3)	0.3069 (3)	0.0534 (18)
O5	0.8163 (6)	0.7345 (4)	0.8560 (3)	0.0537 (17)
O6	0.9820 (7)	0.8025 (4)	0.9332 (3)	0.075 (2)
O7	1.1766 (7)	0.6946 (4)	0.7680 (3)	0.0629 (19)
O8	0.9799 (6)	0.6778 (4)	0.6910 (3)	0.0542 (17)
O9	0.5822 (6)	0.2186 (4)	0.1606 (3)	0.067 (2)
H9	0.6672	0.2439	0.1713	0.080*
O10	0.0507 (7)	0.6040 (4)	0.1616 (3)	0.072 (2)
H10	0.1438	0.5914	0.1739	0.108*
C1	0.5540 (9)	0.6306 (5)	0.1263 (4)	0.037 (2)
C2	0.4161 (9)	0.5569 (5)	0.2704 (5)	0.045 (3)
C3	0.5241 (9)	0.7015 (5)	0.1919 (4)	0.038 (2)
C4	0.4548 (8)	0.6664 (5)	0.2630 (4)	0.038 (2)
C5	0.4174 (8)	0.7333 (5)	0.3239 (4)	0.038 (2)
C6	0.4523 (9)	0.8354 (6)	0.3122 (5)	0.051 (3)
C7	0.5224 (9)	0.8691 (5)	0.2419 (4)	0.038 (2)
C8	0.5601 (8)	0.8039 (5)	0.1809 (4)	0.039 (2)
C9	0.6836 (11)	0.4745 (6)	0.0914 (5)	0.071 (3)
H9A	0.5777	0.4547	0.0783	0.106*
H9B	0.7371	0.4201	0.1152	0.106*
H9C	0.7517	0.4940	0.0464	0.106*
C10	0.9168 (10)	0.8012 (6)	0.8732 (5)	0.047 (3)
C11	1.0597 (9)	0.7266 (6)	0.7303 (5)	0.042 (2)
C12	0.9534 (9)	0.8749 (5)	0.8095 (5)	0.044 (2)
C13	1.0192 (9)	0.8369 (5)	0.7381 (5)	0.045 (2)
C14	1.0600 (9)	0.9033 (5)	0.6794 (5)	0.044 (2)
C15	1.0332 (9)	1.0083 (6)	0.6896 (5)	0.051 (3)
C16	0.9686 (9)	1.0448 (5)	0.7606 (5)	0.048 (3)
C17	0.9298 (9)	0.9776 (6)	0.8195 (5)	0.053 (3)
C18	0.7876 (11)	0.6499 (6)	0.9077 (5)	0.075 (3)
H18A	0.8913	0.6266	0.9239	0.113*
H18B	0.7392	0.5977	0.8821	0.113*
H18C	0.7134	0.6699	0.9511	0.113*
C19	0.8868 (11)	0.5894 (6)	0.3427 (5)	0.069 (3)
H19A	0.8418	0.6523	0.3260	0.083*
H19B	1.0051	0.5965	0.3443	0.083*
C20	0.8082 (12)	0.5679 (6)	0.4215 (5)	0.071 (3)
H20A	0.8753	0.5181	0.4449	0.086*
H20B	0.6991	0.5414	0.4190	0.086*
C21	0.7920 (12)	0.6598 (7)	0.4695 (5)	0.086 (4)
H21A	0.9026	0.6811	0.4762	0.103*
H21B	0.7386	0.7118	0.4420	0.103*
C22	0.6969 (11)	0.6493 (6)	0.5457 (5)	0.057 (3)
H22A	0.7596	0.6076	0.5778	0.069*
H22B	0.5921	0.6184	0.5410	0.069*
C23	0.6647 (11)	0.7515 (6)	0.5812 (5)	0.067 (3)
H23A	0.7711	0.7801	0.5866	0.081*
H23B	0.6098	0.7933	0.5462	0.081*
C24	0.5626 (11)	0.7548 (6)	0.6564 (5)	0.069 (3)
H24A	0.5567	0.8224	0.6745	0.082*
H24B	0.4505	0.7362	0.6497	0.082*
C25	0.6029 (12)	0.1902 (7)	0.0842 (5)	0.079 (3)
H25A	0.6090	0.2481	0.0524	0.119*
H25B	0.5102	0.1521	0.0736	0.119*
H25C	0.7035	0.1509	0.0744	0.119*
C26	0.0639 (12)	0.6378 (7)	0.0859 (5)	0.088 (4)
H26A	−0.0277	0.6825	0.0790	0.132*
H26B	0.0623	0.5825	0.0526	0.132*
H26C	0.1662	0.6716	0.0745	0.132*

	U11	U22	U33	U12	U13	U23
Br1	0.0801 (6)	0.0632 (6)	0.0488 (6)	−0.0097 (5)	0.0118 (5)	−0.0028 (5)
Br2	0.0917 (7)	0.0543 (5)	0.0676 (7)	−0.0064 (5)	0.0128 (6)	−0.0280 (5)
Br3	0.0832 (6)	0.0289 (5)	0.0810 (8)	−0.0096 (4)	−0.0008 (6)	−0.0082 (4)
Br4	0.0886 (7)	0.0470 (5)	0.0542 (6)	−0.0124 (5)	0.0119 (6)	0.0021 (4)
Br5	0.0803 (6)	0.0675 (6)	0.0459 (6)	−0.0036 (5)	0.0112 (5)	−0.0003 (5)
Br6	0.1021 (8)	0.0542 (6)	0.0913 (8)	−0.0069 (6)	0.0031 (7)	0.0319 (5)
Br7	0.0937 (7)	0.0275 (5)	0.1189 (10)	0.0053 (5)	−0.0199 (7)	−0.0075 (5)
Br8	0.1153 (8)	0.0667 (6)	0.0716 (8)	0.0067 (6)	0.0141 (7)	−0.0274 (5)
N1	0.059 (4)	0.035 (4)	0.057 (5)	−0.004 (3)	0.007 (4)	0.000 (3)
N2	0.065 (4)	0.034 (4)	0.047 (5)	−0.006 (3)	−0.003 (4)	−0.009 (3)
O1	0.068 (4)	0.041 (3)	0.053 (4)	0.008 (3)	0.010 (3)	−0.017 (3)
O2	0.115 (5)	0.052 (3)	0.048 (4)	0.017 (3)	−0.027 (4)	−0.018 (3)
O3	0.065 (4)	0.058 (4)	0.091 (5)	−0.011 (3)	−0.031 (4)	0.016 (3)
O4	0.063 (4)	0.029 (3)	0.066 (4)	−0.004 (3)	0.003 (3)	0.003 (3)
O5	0.062 (3)	0.045 (3)	0.054 (4)	−0.019 (3)	−0.006 (3)	0.004 (3)
O6	0.099 (5)	0.082 (4)	0.050 (4)	−0.035 (4)	−0.022 (4)	0.009 (3)
O7	0.073 (4)	0.039 (3)	0.079 (5)	0.002 (3)	−0.018 (4)	−0.012 (3)
O8	0.069 (4)	0.039 (3)	0.054 (4)	−0.006 (3)	−0.005 (3)	−0.013 (3)
O9	0.066 (4)	0.060 (4)	0.074 (5)	−0.017 (3)	0.001 (4)	−0.017 (3)
O10	0.066 (4)	0.081 (4)	0.068 (5)	0.004 (3)	−0.001 (4)	0.022 (3)
C1	0.045 (5)	0.036 (4)	0.029 (5)	0.003 (4)	0.001 (4)	−0.014 (4)
C2	0.032 (5)	0.033 (5)	0.071 (7)	0.006 (4)	−0.014 (5)	0.002 (4)
C3	0.043 (5)	0.030 (4)	0.043 (5)	−0.001 (4)	−0.009 (4)	−0.007 (4)
C4	0.035 (4)	0.041 (4)	0.037 (5)	0.004 (4)	−0.006 (4)	−0.007 (4)
C5	0.020 (4)	0.046 (5)	0.048 (6)	0.002 (4)	−0.007 (4)	−0.002 (4)
C6	0.048 (5)	0.042 (5)	0.063 (6)	0.002 (4)	−0.010 (5)	−0.022 (4)
C7	0.039 (4)	0.031 (4)	0.043 (6)	−0.001 (4)	−0.007 (4)	−0.003 (4)
C8	0.033 (4)	0.036 (4)	0.047 (6)	0.001 (4)	−0.004 (4)	−0.003 (4)
C9	0.110 (7)	0.039 (5)	0.061 (7)	0.008 (5)	−0.004 (6)	−0.009 (5)
C10	0.068 (6)	0.053 (5)	0.022 (5)	0.010 (5)	−0.010 (5)	−0.003 (4)
C11	0.043 (5)	0.047 (5)	0.036 (5)	−0.014 (4)	−0.002 (4)	−0.018 (4)
C12	0.046 (5)	0.041 (5)	0.044 (6)	0.000 (4)	−0.004 (4)	−0.004 (4)
C13	0.048 (5)	0.029 (4)	0.054 (6)	0.003 (4)	0.003 (5)	0.008 (4)
C14	0.049 (5)	0.037 (5)	0.044 (6)	−0.003 (4)	0.008 (4)	−0.001 (4)
C15	0.051 (5)	0.039 (5)	0.061 (6)	−0.008 (4)	0.003 (5)	0.013 (4)
C16	0.043 (5)	0.031 (4)	0.070 (7)	0.003 (4)	−0.015 (5)	−0.011 (4)
C17	0.027 (4)	0.044 (5)	0.085 (7)	0.000 (4)	0.009 (5)	0.002 (5)
C18	0.084 (7)	0.075 (7)	0.064 (7)	−0.020 (6)	0.011 (6)	0.018 (5)
C19	0.095 (7)	0.045 (5)	0.064 (7)	−0.020 (5)	0.010 (6)	−0.019 (5)
C20	0.129 (8)	0.047 (5)	0.036 (6)	−0.027 (5)	0.007 (6)	−0.006 (4)
C21	0.096 (7)	0.091 (7)	0.068 (8)	−0.012 (6)	0.007 (6)	−0.023 (6)
C22	0.073 (6)	0.065 (6)	0.036 (6)	−0.004 (5)	−0.016 (5)	−0.002 (4)
C23	0.086 (7)	0.063 (6)	0.052 (7)	0.015 (5)	−0.015 (6)	−0.002 (5)
C24	0.094 (7)	0.056 (6)	0.054 (7)	0.019 (5)	−0.006 (6)	0.007 (5)
C25	0.121 (8)	0.086 (7)	0.029 (6)	−0.009 (6)	0.008 (6)	−0.016 (5)
C26	0.099 (8)	0.095 (8)	0.065 (8)	0.019 (6)	0.014 (7)	−0.017 (6)

Br1—C5	1.900 (7)	C9—H9A	0.96
Br2—C6	1.907 (8)	C9—H9B	0.96
Br3—C7	1.897 (7)	C9—H9C	0.96
Br4—C8	1.878 (8)	C10—C12	1.510 (11)
Br5—C14	1.923 (8)	C11—C13	1.522 (10)
Br6—C15	1.902 (8)	C12—C17	1.406 (10)
Br7—C16	1.881 (7)	C12—C13	1.417 (10)
Br8—C17	1.906 (9)	C13—C14	1.387 (10)
N1—C19	1.480 (10)	C14—C15	1.439 (10)
N1—H1A	0.89	C15—C16	1.401 (11)
N1—H1B	0.89	C16—C17	1.394 (11)
N1—H1C	0.89	C18—H18A	0.96
N2—C24	1.482 (10)	C18—H18B	0.96
N2—H2A	0.89	C18—H18C	0.96
N2—H2B	0.89	C19—C20	1.502 (11)
N2—H2C	0.89	C19—H19A	0.97
O1—C1	1.342 (8)	C19—H19B	0.97
O1—C9	1.460 (9)	C20—C21	1.509 (12)
O2—C1	1.170 (9)	C20—H20A	0.97
O3—C2	1.247 (9)	C20—H20B	0.97
O4—C2	1.238 (9)	C21—C22	1.489 (11)
O5—C10	1.294 (9)	C21—H21A	0.97
O5—C18	1.468 (10)	C21—H21B	0.97
O6—C10	1.241 (9)	C22—C23	1.529 (11)
O7—C11	1.281 (9)	C22—H22A	0.97
O8—C11	1.214 (9)	C22—H22B	0.97
O9—C25	1.404 (9)	C23—C24	1.494 (11)
O9—H9	0.82	C23—H23A	0.97
O10—C26	1.409 (11)	C23—H23B	0.97
O10—H10	0.82	C24—H24A	0.97
C1—C3	1.510 (10)	C24—H24B	0.97
C2—C4	1.525 (10)	C25—H25A	0.96
C3—C4	1.408 (10)	C25—H25B	0.96
C3—C8	1.432 (10)	C25—H25C	0.96
C4—C5	1.418 (10)	C26—H26A	0.96
C5—C6	1.426 (10)	C26—H26B	0.96
C6—C7	1.392 (11)	C26—H26C	0.96
C7—C8	1.404 (10)
C19—N1—H1A	109.5	C16—C15—Br6	120.9 (6)
C19—N1—H1B	109.5	C14—C15—Br6	119.5 (6)
H1A—N1—H1B	109.5	C17—C16—C15	118.6 (7)
C19—N1—H1C	109.5	C17—C16—Br7	121.7 (6)
H1A—N1—H1C	109.5	C15—C16—Br7	119.6 (6)
H1B—N1—H1C	109.5	C16—C17—C12	122.0 (8)
C24—N2—H2A	109.5	C16—C17—Br8	119.1 (6)
C24—N2—H2B	109.5	C12—C17—Br8	118.9 (6)
H2A—N2—H2B	109.5	O5—C18—H18A	109.5
C24—N2—H2C	109.5	O5—C18—H18B	109.5
H2A—N2—H2C	109.5	H18A—C18—H18B	109.5
H2B—N2—H2C	109.5	O5—C18—H18C	109.5
C1—O1—C9	116.6 (6)	H18A—C18—H18C	109.5
C10—O5—C18	118.2 (7)	H18B—C18—H18C	109.5
C25—O9—H9	109.5	N1—C19—C20	114.6 (7)
C26—O10—H10	109.5	N1—C19—H19A	108.6
O2—C1—O1	124.2 (7)	C20—C19—H19A	108.6
O2—C1—C3	126.4 (7)	N1—C19—H19B	108.6
O1—C1—C3	109.2 (7)	C20—C19—H19B	108.6
O4—C2—O3	125.8 (7)	H19A—C19—H19B	107.6
O4—C2—C4	118.7 (7)	C19—C20—C21	111.4 (7)
O3—C2—C4	115.4 (7)	C19—C20—H20A	109.3
C4—C3—C8	120.5 (7)	C21—C20—H20A	109.3
C4—C3—C1	119.3 (6)	C19—C20—H20B	109.3
C8—C3—C1	120.1 (7)	C21—C20—H20B	109.3
C3—C4—C5	119.8 (7)	H20A—C20—H20B	108.0
C3—C4—C2	117.8 (6)	C22—C21—C20	115.7 (8)
C5—C4—C2	122.3 (7)	C22—C21—H21A	108.4
C4—C5—C6	119.2 (7)	C20—C21—H21A	108.4
C4—C5—Br1	118.3 (5)	C22—C21—H21B	108.4
C6—C5—Br1	122.5 (6)	C20—C21—H21B	108.4
C7—C6—C5	120.5 (7)	H21A—C21—H21B	107.4
C7—C6—Br2	121.6 (6)	C21—C22—C23	109.3 (7)
C5—C6—Br2	117.9 (6)	C21—C22—H22A	109.8
C6—C7—C8	121.1 (7)	C23—C22—H22A	109.8
C6—C7—Br3	119.6 (5)	C21—C22—H22B	109.8
C8—C7—Br3	119.3 (6)	C23—C22—H22B	109.8
C7—C8—C3	118.9 (7)	H22A—C22—H22B	108.3
C7—C8—Br4	121.2 (5)	C24—C23—C22	116.2 (7)
C3—C8—Br4	119.8 (5)	C24—C23—H23A	108.2
O1—C9—H9A	109.5	C22—C23—H23A	108.2
O1—C9—H9B	109.5	C24—C23—H23B	108.2
H9A—C9—H9B	109.5	C22—C23—H23B	108.2
O1—C9—H9C	109.5	H23A—C23—H23B	107.4
H9A—C9—H9C	109.5	N2—C24—C23	114.9 (7)
H9B—C9—H9C	109.5	N2—C24—H24A	108.5
O6—C10—O5	124.5 (7)	C23—C24—H24A	108.5
O6—C10—C12	123.5 (8)	N2—C24—H24B	108.5
O5—C10—C12	111.9 (7)	C23—C24—H24B	108.5
O8—C11—O7	126.5 (7)	H24A—C24—H24B	107.5
O8—C11—C13	118.8 (7)	O9—C25—H25A	109.5
O7—C11—C13	114.7 (7)	O9—C25—H25B	109.5
C17—C12—C13	120.0 (7)	H25A—C25—H25B	109.5
C17—C12—C10	122.7 (7)	O9—C25—H25C	109.5
C13—C12—C10	117.3 (6)	H25A—C25—H25C	109.5
C14—C13—C12	118.4 (7)	H25B—C25—H25C	109.5
C14—C13—C11	122.0 (7)	O10—C26—H26A	109.5
C12—C13—C11	119.2 (7)	O10—C26—H26B	109.5
C13—C14—C15	121.4 (7)	H26A—C26—H26B	109.5
C13—C14—Br5	119.2 (5)	O10—C26—H26C	109.5
C15—C14—Br5	119.4 (6)	H26A—C26—H26C	109.5
C16—C15—C14	119.6 (7)	H26B—C26—H26C	109.5
C9—O1—C1—O2	−5.1 (11)	O5—C10—C12—C17	125.7 (8)
C9—O1—C1—C3	171.0 (6)	O6—C10—C12—C13	120.5 (9)
O2—C1—C3—C4	115.6 (9)	O5—C10—C12—C13	−56.4 (9)
O1—C1—C3—C4	−60.4 (9)	C17—C12—C13—C14	0.4 (12)
O2—C1—C3—C8	−62.0 (11)	C10—C12—C13—C14	−177.5 (7)
O1—C1—C3—C8	122.0 (7)	C17—C12—C13—C11	174.1 (7)
C8—C3—C4—C5	1.2 (11)	C10—C12—C13—C11	−3.9 (11)
C1—C3—C4—C5	−176.4 (7)	O8—C11—C13—C14	−72.6 (10)
C8—C3—C4—C2	178.7 (7)	O7—C11—C13—C14	108.3 (9)
C1—C3—C4—C2	1.1 (10)	O8—C11—C13—C12	114.0 (9)
O4—C2—C4—C3	108.4 (9)	O7—C11—C13—C12	−65.1 (9)
O3—C2—C4—C3	−69.7 (9)	C12—C13—C14—C15	−1.5 (12)
O4—C2—C4—C5	−74.1 (10)	C11—C13—C14—C15	−174.9 (7)
O3—C2—C4—C5	107.8 (9)	C12—C13—C14—Br5	178.1 (6)
C3—C4—C5—C6	−0.6 (11)	C11—C13—C14—Br5	4.7 (11)
C2—C4—C5—C6	−178.0 (7)	C13—C14—C15—C16	1.7 (12)
C3—C4—C5—Br1	177.0 (5)	Br5—C14—C15—C16	−177.8 (6)
C2—C4—C5—Br1	−0.4 (9)	C13—C14—C15—Br6	179.2 (6)
C4—C5—C6—C7	−0.1 (11)	Br5—C14—C15—Br6	−0.3 (9)
Br1—C5—C6—C7	−177.6 (6)	C14—C15—C16—C17	−0.9 (12)
C4—C5—C6—Br2	179.3 (5)	Br6—C15—C16—C17	−178.4 (6)
Br1—C5—C6—Br2	1.8 (9)	C14—C15—C16—Br7	176.5 (6)
C5—C6—C7—C8	0.2 (12)	Br6—C15—C16—Br7	−1.0 (9)
Br2—C6—C7—C8	−179.2 (6)	C15—C16—C17—C12	−0.1 (12)
C5—C6—C7—Br3	178.1 (5)	Br7—C16—C17—C12	−177.4 (6)
Br2—C6—C7—Br3	−1.3 (9)	C15—C16—C17—Br8	−177.4 (6)
C6—C7—C8—C3	0.4 (11)	Br7—C16—C17—Br8	5.3 (9)
Br3—C7—C8—C3	−177.5 (5)	C13—C12—C17—C16	0.4 (12)
C6—C7—C8—Br4	−175.4 (6)	C10—C12—C17—C16	178.2 (8)
Br3—C7—C8—Br4	6.7 (9)	C13—C12—C17—Br8	177.7 (6)
C4—C3—C8—C7	−1.1 (11)	C10—C12—C17—Br8	−4.5 (10)
C1—C3—C8—C7	176.5 (7)	N1—C19—C20—C21	−162.4 (8)
C4—C3—C8—Br4	174.8 (6)	C19—C20—C21—C22	172.8 (8)
C1—C3—C8—Br4	−7.6 (10)	C20—C21—C22—C23	−169.9 (8)
C18—O5—C10—O6	−5.4 (11)	C21—C22—C23—C24	177.0 (8)
C18—O5—C10—C12	171.5 (6)	C22—C23—C24—N2	54.7 (11)
O6—C10—C12—C17	−57.4 (11)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O8i	0.89	2.01	2.890 (7)	171
N1—H1B···O10ii	0.89	1.99	2.840 (8)	158
N1—H1C···O4	0.89	2.02	2.892 (8)	167
N2—H2A···O4iii	0.89	2.00	2.877 (7)	168
N2—H2B···O9iii	0.89	2.04	2.885 (8)	159
N2—H2C···O8	0.89	1.99	2.859 (8)	165
O9—H9···O7i	0.82	1.96	2.743 (8)	160
O10—H10···O3	0.82	1.92	2.685 (8)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O8i	0.89	2.01	2.890 (7)	171
N1—H1B⋯O10ii	0.89	1.99	2.840 (8)	158
N1—H1C⋯O4	0.89	2.02	2.892 (8)	167
N2—H2A⋯O4iii	0.89	2.00	2.877 (7)	168
N2—H2B⋯O9iii	0.89	2.04	2.885 (8)	159
N2—H2C⋯O8	0.89	1.99	2.859 (8)	165
O9—H9⋯O7i	0.82	1.96	2.743 (8)	160
O10—H10⋯O3	0.82	1.92	2.685 (8)	154

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