3,3′-Bis(cyclo­hexyl­meth­yl)-1,1′-propyl­enedibenzimidazolium dibromide monohydrate

The title compound, C₃₁H₄₂N₄²⁺·2Br⁻·H₂O, was synthesized from 1,1′-propyl­endibenzimidazole and cyclo­hexyl­methyl bromide in dimethyl­formamide solution. In the mol­ecule, the benzimidazole ring systems are connected to the cyclohexane rings by methyl­ene groups and to each other by a propyl­ene group. The crystal structure is stabilized by inter­molecular O—H...Br hydrogen bonds involving the H atoms of the water mol­ecule.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.045
• wR factor = 0.110
• Data-to-parameter ratio = 16.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.68 mm
PLAT155_ALERT_4_C The Triclinic Unitcell is NOT Reduced ..........          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.71 Ratio
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N2     -   C7      ..       6.88 su

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   5 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA; data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

3,3'-Bis(cyclohexylmethyl)-1,1'-propylenedibenzimidazolium dibromide monohydrate

Crystal data

C31H42N4^2+·2Br^−·H2O	Z = 2
Mr = 648.50	F(000) = 672
Triclinic, P1	Dx = 1.434 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.2538 (5) Å	Cell parameters from 42573 reflections
b = 12.5925 (8) Å	θ = 1.9–28.0°
c = 15.4610 (9) Å	µ = 2.73 mm^−1
α = 105.049 (5)°	T = 296 K
β = 105.593 (4)°	Prism, colourless
γ = 110.034 (4)°	0.68 × 0.55 × 0.36 mm
V = 1502.14 (18) Å^3

Data collection

STOE IPDS-II diffractometer	5915 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	4567 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.049
Detector resolution: 6.67 pixels mm^-1	θmax = 26.0°, θmin = 1.9°
ω scans	h = −11→11
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −15→15
Tmin = 0.258, Tmax = 0.440	l = −19→19
29924 measured reflections

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.047P)^2 + 1.0857P] where P = (Fo^2 + 2Fc^2)/3
5915 reflections	(Δ/σ)max < 0.001
351 parameters	Δρmax = 0.57 e Å^−3
3 restraints	Δρmin = −0.65 e Å^−3

Special details

Experimental. ¹H NMR (DMSO-d₆): δ 1.67 (d, CH₃, 6H), 1.87 (m, ring methylene, 2H), 2.08 (t, ring methylene, 2H), 3.24 (m, ring methylene, 2H), 3.70 (t, ring methylene, 2H), 3.92 (t, CH₂CH₂-pyrrolidine, 2H), 4.91 (t, CH₂CH₂-pyrrolidine, 2H), 7.74 (m, Ar–H, 2H), 8.19 (m, Ar–H, 2H), 9.58 (s, 2-CH, 1H), 10.01 (s, pyrrolidine-1H, 1H). ¹³C NMR(DMSO-d₆): δ 22.07, 23.16, 43.53, 51.35, 52.08, 54.31, 114.49, 114.64, 127.14, 127.23, 131.03, 131.73, 132.04.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
N1	0.1709 (3)	0.1742 (2)	0.18214 (19)	0.0479 (8)
N2	0.3274 (3)	0.1760 (2)	0.0984 (2)	0.0505 (9)
N3	0.1245 (3)	0.2576 (2)	0.46616 (18)	0.0454 (8)
N4	0.2893 (3)	0.2092 (3)	0.56092 (18)	0.0487 (8)
C1	0.0752 (4)	0.1608 (3)	0.0896 (2)	0.0443 (9)
C2	−0.0870 (4)	0.1455 (3)	0.0496 (3)	0.0527 (11)
C3	−0.1429 (5)	0.1338 (3)	−0.0460 (3)	0.0610 (12)
C4	−0.0426 (5)	0.1367 (3)	−0.0985 (3)	0.0627 (13)
C5	0.1181 (5)	0.1506 (3)	−0.0594 (2)	0.0560 (11)
C6	0.1757 (4)	0.1632 (3)	0.0371 (2)	0.0461 (10)
C7	0.4747 (5)	0.1738 (4)	0.0744 (3)	0.0737 (17)
C8	0.6169 (5)	0.3006 (4)	0.1086 (3)	0.0685 (14)
C9	0.5735 (6)	0.3770 (4)	0.0546 (3)	0.0763 (17)
C10	0.7222 (6)	0.5008 (5)	0.0893 (4)	0.0976 (19)
C11	0.7916 (7)	0.5678 (5)	0.1977 (4)	0.107 (2)
C12	0.8348 (7)	0.4949 (6)	0.2533 (4)	0.113 (2)
C13	0.6876 (6)	0.3712 (5)	0.2185 (3)	0.0924 (19)
C14	0.3177 (4)	0.1822 (3)	0.1832 (2)	0.0540 (11)
C15	0.1164 (4)	0.1765 (3)	0.2631 (2)	0.0526 (11)
C16	0.1414 (4)	0.3035 (3)	0.3208 (2)	0.0523 (11)
C17	0.0593 (5)	0.3043 (3)	0.3937 (2)	0.0538 (11)
C18	0.2765 (4)	0.2628 (3)	0.4977 (2)	0.0498 (10)
C19	0.1399 (4)	0.1685 (3)	0.5735 (2)	0.0424 (9)
C20	0.0882 (4)	0.1074 (3)	0.6304 (2)	0.0500 (10)
C21	−0.0714 (5)	0.0806 (3)	0.6240 (2)	0.0569 (11)
C22	−0.1773 (5)	0.1119 (3)	0.5642 (3)	0.0566 (12)
C23	−0.1268 (4)	0.1728 (3)	0.5077 (2)	0.0504 (11)
C24	0.0344 (4)	0.2000 (3)	0.5135 (2)	0.0417 (9)
C25	0.4414 (4)	0.1973 (3)	0.6089 (2)	0.0550 (11)
C26	0.5390 (4)	0.2883 (3)	0.7134 (2)	0.0469 (10)
C27	0.5840 (5)	0.4195 (3)	0.7217 (3)	0.0584 (11)
C28	0.6854 (5)	0.5083 (3)	0.8267 (3)	0.0678 (14)
C29	0.8407 (5)	0.4965 (3)	0.8716 (3)	0.0707 (12)
C30	0.8004 (5)	0.3652 (4)	0.8609 (3)	0.0681 (12)
C31	0.6970 (4)	0.2760 (3)	0.7560 (3)	0.0560 (11)
O1	0.4327 (4)	0.0642 (4)	0.3442 (3)	0.0864 (16)
Br1	0.63098 (5)	0.36704 (4)	0.44457 (3)	0.0749 (2)
Br2	0.64470 (5)	−0.00287 (4)	0.20436 (3)	0.0671 (1)
H2	−0.15410	0.14340	0.08500	0.0640*
H3	−0.25100	0.12360	−0.07620	0.0730*
H4	−0.08560	0.12900	−0.16280	0.0750*
H5	0.18420	0.15140	−0.09540	0.0670*
H7A	0.43660	0.13330	0.00440	0.0880*
H7B	0.51670	0.12580	0.10440	0.0880*
H8	0.70770	0.28780	0.09400	0.0820*
H9A	0.48050	0.38940	0.06480	0.0920*
H9B	0.53880	0.33350	−0.01470	0.0920*
H10A	0.80910	0.48860	0.07060	0.1170*
H10B	0.68780	0.55030	0.05760	0.1170*
H11A	0.89130	0.64280	0.21690	0.1280*
H11B	0.71000	0.59060	0.21490	0.1280*
H12A	0.86710	0.53940	0.32210	0.1350*
H12B	0.92930	0.48330	0.24490	0.1350*
H13A	0.59990	0.38310	0.23650	0.1110*
H13B	0.72240	0.32270	0.25120	0.1110*
H14	0.40330	0.19110	0.23680	0.0650*
H15A	0.17900	0.14960	0.30620	0.0630*
H15B	−0.00120	0.11950	0.23750	0.0630*
H16A	0.09540	0.33610	0.27590	0.0630*
H16B	0.26040	0.35710	0.35530	0.0630*
H17A	0.07840	0.38750	0.42750	0.0650*
H17B	−0.06050	0.25420	0.35900	0.0650*
H18	0.36120	0.29870	0.47820	0.0600*
H20	0.15790	0.08600	0.67040	0.0600*
H21	−0.11090	0.03980	0.66120	0.0680*
H22	−0.28510	0.09110	0.56230	0.0680*
H23	−0.19680	0.19440	0.46800	0.0600*
H25A	0.51250	0.21010	0.57280	0.0660*
H25B	0.40910	0.11480	0.60730	0.0660*
H26	0.47040	0.26930	0.75080	0.0560*
H27A	0.64810	0.43850	0.68280	0.0700*
H27B	0.48240	0.42810	0.69660	0.0700*
H28A	0.71590	0.59140	0.82990	0.0810*
H28B	0.61690	0.49370	0.86410	0.0810*
H29A	0.89610	0.54990	0.94020	0.0850*
H29B	0.91680	0.52230	0.84040	0.0850*
H30A	0.90380	0.35840	0.88420	0.0820*
H30B	0.73930	0.34400	0.90070	0.0820*
H31A	0.76330	0.29100	0.71750	0.0670*
H31B	0.66760	0.19290	0.75260	0.0670*
H1A	0.478 (6)	0.138 (2)	0.377 (3)	0.10 (2)*
H1B	0.479 (5)	0.041 (4)	0.310 (3)	0.091 (18)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0516 (16)	0.0443 (14)	0.0414 (14)	0.0150 (12)	0.0142 (12)	0.0201 (12)
N2	0.0528 (16)	0.0477 (15)	0.0477 (15)	0.0215 (13)	0.0166 (13)	0.0182 (12)
N3	0.0410 (14)	0.0505 (15)	0.0395 (14)	0.0161 (12)	0.0115 (11)	0.0202 (12)
N4	0.0384 (14)	0.0581 (16)	0.0387 (14)	0.0179 (12)	0.0057 (11)	0.0171 (12)
C1	0.0527 (18)	0.0323 (14)	0.0399 (16)	0.0152 (13)	0.0118 (14)	0.0139 (12)
C2	0.054 (2)	0.0455 (18)	0.054 (2)	0.0216 (15)	0.0158 (16)	0.0187 (15)
C3	0.059 (2)	0.055 (2)	0.056 (2)	0.0275 (17)	0.0042 (18)	0.0185 (17)
C4	0.080 (3)	0.058 (2)	0.0386 (18)	0.0320 (19)	0.0086 (18)	0.0152 (16)
C5	0.076 (2)	0.0466 (18)	0.0450 (18)	0.0278 (17)	0.0226 (18)	0.0175 (15)
C6	0.0574 (19)	0.0345 (15)	0.0420 (17)	0.0193 (14)	0.0148 (15)	0.0147 (13)
C7	0.081 (3)	0.071 (3)	0.072 (3)	0.042 (2)	0.025 (2)	0.026 (2)
C8	0.065 (2)	0.080 (3)	0.069 (2)	0.040 (2)	0.029 (2)	0.028 (2)
C9	0.076 (3)	0.081 (3)	0.083 (3)	0.042 (2)	0.034 (2)	0.036 (2)
C10	0.078 (3)	0.092 (3)	0.118 (4)	0.029 (3)	0.040 (3)	0.044 (3)
C11	0.080 (3)	0.089 (4)	0.112 (4)	0.012 (3)	0.046 (3)	0.004 (3)
C12	0.075 (3)	0.131 (5)	0.085 (4)	0.012 (3)	0.032 (3)	0.017 (3)
C13	0.082 (3)	0.112 (4)	0.064 (3)	0.031 (3)	0.023 (2)	0.028 (3)
C14	0.054 (2)	0.0524 (19)	0.0468 (19)	0.0185 (16)	0.0117 (16)	0.0216 (15)
C15	0.059 (2)	0.0484 (18)	0.0449 (18)	0.0148 (15)	0.0187 (16)	0.0239 (15)
C16	0.060 (2)	0.0462 (18)	0.0454 (18)	0.0175 (15)	0.0159 (16)	0.0233 (15)
C17	0.055 (2)	0.060 (2)	0.0481 (19)	0.0266 (17)	0.0150 (16)	0.0277 (16)
C18	0.0378 (16)	0.061 (2)	0.0415 (17)	0.0141 (14)	0.0104 (14)	0.0227 (15)
C19	0.0391 (16)	0.0421 (16)	0.0348 (15)	0.0131 (13)	0.0099 (13)	0.0101 (12)
C20	0.060 (2)	0.0441 (17)	0.0383 (16)	0.0199 (15)	0.0145 (15)	0.0142 (13)
C21	0.071 (2)	0.0529 (19)	0.0455 (19)	0.0203 (17)	0.0302 (18)	0.0194 (15)
C22	0.053 (2)	0.056 (2)	0.057 (2)	0.0192 (16)	0.0292 (17)	0.0152 (17)
C23	0.0442 (18)	0.0541 (19)	0.0468 (18)	0.0222 (15)	0.0134 (15)	0.0148 (15)
C24	0.0405 (16)	0.0405 (15)	0.0345 (15)	0.0131 (13)	0.0109 (13)	0.0110 (12)
C25	0.0458 (18)	0.059 (2)	0.0480 (19)	0.0246 (16)	0.0072 (15)	0.0126 (16)
C26	0.0418 (17)	0.0479 (17)	0.0439 (17)	0.0182 (14)	0.0112 (14)	0.0156 (14)
C27	0.064 (2)	0.0518 (19)	0.056 (2)	0.0281 (17)	0.0163 (18)	0.0202 (16)
C28	0.070 (3)	0.050 (2)	0.067 (2)	0.0229 (18)	0.019 (2)	0.0119 (18)
C29	0.059 (2)	0.057 (2)	0.063 (2)	0.0140 (18)	0.0089 (19)	0.0058 (18)
C30	0.055 (2)	0.068 (2)	0.059 (2)	0.0223 (18)	0.0022 (18)	0.0196 (19)
C31	0.0502 (19)	0.0517 (19)	0.056 (2)	0.0237 (16)	0.0087 (16)	0.0172 (16)
O1	0.075 (2)	0.088 (3)	0.104 (3)	0.033 (2)	0.045 (2)	0.043 (2)
Br1	0.0603 (2)	0.0779 (3)	0.0715 (3)	0.0206 (2)	0.0283 (2)	0.0181 (2)
Br2	0.0622 (2)	0.0797 (3)	0.0644 (2)	0.0346 (2)	0.0226 (2)	0.0338 (2)

Geometric parameters (Å, º)

O1—H1A	0.82 (3)	C2—H2	0.9300
O1—H1B	0.82 (5)	C3—H3	0.9300
N1—C1	1.397 (4)	C4—H4	0.9300
N1—C14	1.323 (5)	C5—H5	0.9300
N1—C15	1.467 (4)	C7—H7B	0.9700
N2—C6	1.395 (5)	C7—H7A	0.9700
N2—C14	1.322 (4)	C8—H8	0.9800
N2—C7	1.513 (6)	C9—H9A	0.9700
N3—C18	1.331 (5)	C9—H9B	0.9700
N3—C24	1.395 (5)	C10—H10B	0.9700
N3—C17	1.479 (4)	C10—H10A	0.9700
N4—C25	1.482 (5)	C11—H11B	0.9700
N4—C18	1.327 (5)	C11—H11A	0.9700
N4—C19	1.387 (5)	C12—H12A	0.9700
C1—C6	1.387 (5)	C12—H12B	0.9700
C1—C2	1.383 (6)	C13—H13B	0.9700
C2—C3	1.378 (6)	C13—H13A	0.9700
C3—C4	1.385 (7)	C14—H14	0.9300
C4—C5	1.375 (7)	C15—H15B	0.9700
C5—C6	1.388 (4)	C15—H15A	0.9700
C7—C8	1.519 (7)	C16—H16B	0.9700
C8—C13	1.525 (6)	C16—H16A	0.9700
C8—C9	1.512 (7)	C17—H17B	0.9700
C9—C10	1.520 (8)	C17—H17A	0.9700
C10—C11	1.500 (8)	C18—H18	0.9300
C11—C12	1.489 (9)	C20—H20	0.9300
C12—C13	1.513 (9)	C21—H21	0.9300
C15—C16	1.517 (5)	C22—H22	0.9300
C16—C17	1.519 (5)	C23—H23	0.9300
C19—C24	1.393 (5)	C25—H25B	0.9700
C19—C20	1.386 (5)	C25—H25A	0.9700
C20—C21	1.367 (6)	C26—H26	0.9800
C21—C22	1.392 (6)	C27—H27A	0.9700
C22—C23	1.375 (5)	C27—H27B	0.9700
C23—C24	1.383 (6)	C28—H28A	0.9700
C25—C26	1.511 (4)	C28—H28B	0.9700
C26—C31	1.512 (6)	C29—H29B	0.9700
C26—C27	1.520 (5)	C29—H29A	0.9700
C27—C28	1.512 (6)	C30—H30A	0.9700
C28—C29	1.494 (7)	C30—H30B	0.9700
C29—C30	1.517 (6)	C31—H31B	0.9700
C30—C31	1.514 (6)	C31—H31A	0.9700
Br1···C13	3.682 (5)	H7A···H5	2.5500
Br1···C18	3.495 (4)	H7A···H9B	2.5000
Br1···O1	3.305 (5)	H7B···Br2	2.8400
Br2···O1	3.421 (4)	H7B···H13B	2.5400
Br1···H13A	3.2200	H8···H2^i	2.5500
Br1···H14	3.0200	H8···H10A	2.5400
Br1···H23^i	3.1400	H8···H12B	2.5900
Br1···H17A^ii	2.9900	H9A···C6	3.0800
Br1···H18	2.5900	H9A···N2	2.8300
Br1···H1A	2.50 (3)	H9A···H10B^xi	2.5600
Br2···H7B	2.8400	H9A···H28B^ii	2.1900
Br2···H15B^i	2.9300	H9A···C28^ii	2.9100
Br2···H17B^i	3.1700	H9B···H30B^x	2.5300
Br2···H3^iii	3.2000	H9B···H7A	2.5000
Br2···H7A^iv	2.9600	H10A···H29A^x	2.5600
Br2···H20^v	2.9400	H10A···H8	2.5400
Br2···H1B	2.60 (5)	H10A···C29^viii	3.0500
O1···Br2	3.421 (4)	H10A···H30A^viii	2.4600
O1···C14	3.334 (6)	H10A···H30B^x	2.5400
O1···Br1	3.305 (5)	H10B···H9A^xi	2.5600
O1···H21^vi	2.7800	H11B···H27B^ii	2.5100
O1···H22^vi	2.9100	H12B···H8	2.5900
O1···H14	2.6100	H12B···H29B^viii	2.1900
O1···H15A	2.8900	H13A···Br1	3.2200
O1···H31B^v	2.8700	H13A···C14	2.6700
N1···N2	2.185 (4)	H13A···H14	2.4800
N1···C4^iii	3.431 (5)	H13A···N2	2.7300
N2···N1	2.185 (4)	H13B···H7B	2.5400
N2···C3^iii	3.441 (5)	H14···O1	2.6100
N1···H28A^ii	2.8500	H14···C13	2.9600
N2···H9A	2.8300	H14···Br1	3.0200
N2···H13A	2.7300	H14···H13A	2.4800
N3···H15A	2.7600	H14···H15A	2.5500
N4···H27B	2.6100	H14···H1A	2.4300
C1···C5^iii	3.548 (5)	H15A···H18	2.5000
C1···C6^iii	3.576 (5)	H15A···H21^vi	2.4700
C2···C6^iii	3.478 (5)	H15A···O1	2.8900
C3···N2^iii	3.441 (5)	H15A···N3	2.7600
C3···C14^iii	3.509 (5)	H15A···C18	2.6700
C4···C14^iii	3.577 (5)	H15A···H14	2.5500
C4···N1^iii	3.431 (5)	H15B···Br2^ix	2.9300
C5···C1^iii	3.548 (5)	H15B···C2	2.9300
C6···C2^iii	3.478 (5)	H15B···H2	2.5500
C6···C1^iii	3.576 (5)	H15B···H17B	2.5000
C13···C14	3.228 (7)	H16A···C1	3.0500
C13···Br1	3.682 (5)	H16B···C18	2.7500
C14···C13	3.228 (7)	H16B···H18	2.2900
C14···C3^iii	3.509 (5)	H17A···Br1^ii	2.9900
C14···O1	3.334 (6)	H17B···Br2^ix	3.1700
C14···C4^iii	3.577 (5)	H17B···C23	2.8700
C15···C18	3.239 (4)	H17B···H23	2.4800
C18···C15	3.239 (4)	H17B···H15B	2.5000
C18···C27	3.360 (5)	H18···C15	3.0800
C18···Br1	3.495 (4)	H18···C16	2.7500
C19···C20^vi	3.489 (4)	H18···Br1	2.5900
C19···C21^vi	3.491 (5)	H18···H15A	2.5000
C20···C19^vi	3.489 (4)	H18···H16B	2.2900
C20···C24^vi	3.519 (5)	H18···H25A	2.4800
C21···C19^vi	3.491 (5)	H20···Br2^v	2.9400
C22···C25^vi	3.584 (5)	H20···C25	3.0400
C24···C20^vi	3.519 (5)	H21···H4^xii	2.5700
C25···C22^vi	3.584 (5)	H21···O1^vi	2.7800
C27···C18	3.360 (5)	H21···H15A^vi	2.4700
C1···H16A	3.0500	H22···O1^vi	2.9100
C1···H28A^ii	2.7500	H23···Br1^ix	3.1400
C2···H15B	2.9300	H23···H17B	2.4800
C4···H30A^vii	3.0600	H23···C17	2.9800
C5···H7A	2.9500	H25A···H27A	2.5600
C6···H28A^ii	2.8700	H25A···H18	2.4800
C6···H9A	3.0800	H25A···H31A	2.4200
C7···H5	3.0800	H25B···H31B	2.4700
C9···H28B^ii	3.0700	H25B···C20	3.0600
C12···H29B^viii	3.0700	H25B···C22^vi	2.9300
C13···H14	2.9600	H26···C19	3.0800
C14···H13A	2.6700	H26···H28B	2.5300
C14···H28A^ii	3.0200	H26···H30B	2.5700
C15···H2	3.0000	H27A···H31A	2.5400
C15···H18	3.0800	H27A···H25A	2.5600
C16···H18	2.7500	H27B···N4	2.6100
C17···H23	2.9800	H27B···H11B^ii	2.5100
C18···H16B	2.7500	H27B···C18	2.8700
C18···H15A	2.6700	H28A···N1^ii	2.8500
C18···H27B	2.8700	H28A···C14^ii	3.0200
C19···H26	3.0800	H28A···C1^ii	2.7500
C20···H25B	3.0600	H28A···C6^ii	2.8700
C22···H25B^vi	2.9300	H28B···C9^ii	3.0700
C23···H17B	2.8700	H28B···H26	2.5300
C25···H20	3.0400	H28B···H9A^ii	2.1900
C28···H9A^ii	2.9100	H29A···H10A^xii	2.5600
C29···H10A^viii	3.0500	H29A···H30A^xiii	2.5200
H1A···H14	2.4300	H29B···H12B^viii	2.1900
H1A···Br1	2.50 (3)	H29B···C12^viii	3.0700
H1B···H31B^v	2.5600	H30A···H10A^viii	2.4600
H1B···Br2	2.60 (5)	H30A···C4^xiv	3.0600
H2···H15B	2.5500	H30A···H29A^xiii	2.5200
H2···C15	3.0000	H30B···H9B^xii	2.5300
H2···H8^ix	2.5500	H30B···H10A^xii	2.5400
H3···Br2^iii	3.2000	H30B···H26	2.5700
H4···H21^x	2.5700	H31A···H27A	2.5400
H5···C7	3.0800	H31A···H25A	2.4200
H5···H7A	2.5500	H31B···H1B^v	2.5600
H7A···Br2^iv	2.9600	H31B···O1^v	2.8700
H7A···C5	2.9500	H31B···H25B	2.4700
H1A—O1—H1B	115 (5)	C11—C10—H10B	109.00
C1—N1—C15	125.8 (3)	H10A—C10—H10B	108.00
C14—N1—C15	126.2 (3)	C11—C10—H10A	109.00
C1—N1—C14	108.0 (3)	C10—C11—H11A	109.00
C6—N2—C7	128.4 (3)	C10—C11—H11B	109.00
C7—N2—C14	124.1 (3)	C12—C11—H11B	109.00
C6—N2—C14	107.4 (3)	H11A—C11—H11B	108.00
C17—N3—C18	126.8 (3)	C12—C11—H11A	109.00
C18—N3—C24	108.3 (3)	C11—C12—H12B	109.00
C17—N3—C24	124.9 (3)	C13—C12—H12A	110.00
C18—N4—C19	108.9 (3)	C13—C12—H12B	109.00
C18—N4—C25	124.0 (3)	H12A—C12—H12B	108.00
C19—N4—C25	127.1 (3)	C11—C12—H12A	109.00
N1—C1—C2	131.4 (3)	C8—C13—H13A	109.00
N1—C1—C6	106.1 (3)	C8—C13—H13B	109.00
C2—C1—C6	122.5 (3)	C12—C13—H13B	109.00
C1—C2—C3	115.8 (4)	H13A—C13—H13B	108.00
C2—C3—C4	121.8 (4)	C12—C13—H13A	109.00
C3—C4—C5	122.6 (4)	N2—C14—H14	124.00
C4—C5—C6	115.9 (4)	N1—C14—H14	124.00
N2—C6—C5	131.5 (4)	N1—C15—H15A	109.00
C1—C6—C5	121.3 (4)	N1—C15—H15B	109.00
N2—C6—C1	107.2 (3)	C16—C15—H15B	109.00
N2—C7—C8	113.5 (4)	H15A—C15—H15B	108.00
C7—C8—C13	112.9 (4)	C16—C15—H15A	109.00
C9—C8—C13	110.9 (4)	C15—C16—H16B	109.00
C7—C8—C9	113.6 (4)	C17—C16—H16A	109.00
C8—C9—C10	111.2 (4)	C17—C16—H16B	109.00
C9—C10—C11	111.9 (5)	H16A—C16—H16B	108.00
C10—C11—C12	113.5 (5)	C15—C16—H16A	109.00
C11—C12—C13	110.8 (5)	N3—C17—H17A	109.00
C8—C13—C12	112.9 (4)	N3—C17—H17B	109.00
N1—C14—N2	111.4 (3)	C16—C17—H17B	109.00
N1—C15—C16	112.1 (3)	H17A—C17—H17B	108.00
C15—C16—C17	113.1 (3)	C16—C17—H17A	109.00
N3—C17—C16	112.5 (4)	N3—C18—H18	125.00
N3—C18—N4	110.1 (3)	N4—C18—H18	125.00
N4—C19—C20	132.0 (3)	C21—C20—H20	122.00
C20—C19—C24	121.6 (4)	C19—C20—H20	122.00
N4—C19—C24	106.4 (3)	C20—C21—H21	119.00
C19—C20—C21	115.9 (3)	C22—C21—H21	119.00
C20—C21—C22	122.7 (4)	C23—C22—H22	119.00
C21—C22—C23	121.7 (4)	C21—C22—H22	119.00
C22—C23—C24	116.0 (4)	C22—C23—H23	122.00
N3—C24—C19	106.4 (3)	C24—C23—H23	122.00
C19—C24—C23	122.1 (3)	N4—C25—H25A	109.00
N3—C24—C23	131.6 (3)	N4—C25—H25B	109.00
N4—C25—C26	112.1 (3)	C26—C25—H25B	109.00
C25—C26—C31	109.3 (3)	H25A—C25—H25B	108.00
C27—C26—C31	109.6 (3)	C26—C25—H25A	109.00
C25—C26—C27	112.0 (3)	C27—C26—H26	109.00
C26—C27—C28	110.6 (3)	C31—C26—H26	109.00
C27—C28—C29	112.5 (4)	C25—C26—H26	109.00
C28—C29—C30	111.1 (4)	C26—C27—H27B	110.00
C29—C30—C31	111.7 (4)	C28—C27—H27A	110.00
C26—C31—C30	111.7 (3)	C26—C27—H27A	110.00
C3—C2—H2	122.00	H27A—C27—H27B	108.00
C1—C2—H2	122.00	C28—C27—H27B	110.00
C2—C3—H3	119.00	C27—C28—H28A	109.00
C4—C3—H3	119.00	C27—C28—H28B	109.00
C5—C4—H4	119.00	C29—C28—H28B	109.00
C3—C4—H4	119.00	H28A—C28—H28B	108.00
C4—C5—H5	122.00	C29—C28—H28A	109.00
C6—C5—H5	122.00	C28—C29—H29B	109.00
N2—C7—H7B	109.00	C30—C29—H29A	109.00
C8—C7—H7A	109.00	C30—C29—H29B	109.00
C8—C7—H7B	109.00	H29A—C29—H29B	108.00
H7A—C7—H7B	108.00	C28—C29—H29A	109.00
N2—C7—H7A	109.00	C29—C30—H30B	109.00
C9—C8—H8	106.00	C31—C30—H30A	109.00
C13—C8—H8	106.00	C29—C30—H30A	109.00
C7—C8—H8	106.00	H30A—C30—H30B	108.00
C8—C9—H9B	109.00	C31—C30—H30B	109.00
C10—C9—H9A	109.00	C26—C31—H31A	109.00
C10—C9—H9B	109.00	C26—C31—H31B	109.00
H9A—C9—H9B	108.00	C30—C31—H31B	109.00
C8—C9—H9A	109.00	H31A—C31—H31B	108.00
C9—C10—H10A	109.00	C30—C31—H31A	109.00
C9—C10—H10B	109.00
C14—N1—C1—C2	178.1 (4)	C1—C2—C3—C4	0.3 (6)
C15—N1—C1—C2	−0.8 (6)	C2—C3—C4—C5	0.4 (6)
C14—N1—C1—C6	−0.8 (4)	C3—C4—C5—C6	−0.8 (6)
C15—N1—C1—C6	−179.7 (3)	C4—C5—C6—C1	0.5 (5)
C1—N1—C15—C16	−84.7 (4)	C4—C5—C6—N2	178.4 (4)
C14—N1—C15—C16	96.7 (4)	N2—C7—C8—C9	−67.7 (5)
C1—N1—C14—N2	0.5 (4)	N2—C7—C8—C13	59.5 (5)
C15—N1—C14—N2	179.3 (3)	C7—C8—C13—C12	177.1 (5)
C7—N2—C6—C1	174.9 (4)	C7—C8—C9—C10	−177.9 (4)
C14—N2—C7—C8	−84.1 (5)	C13—C8—C9—C10	53.8 (6)
C7—N2—C14—N1	−175.7 (3)	C9—C8—C13—C12	−54.2 (6)
C14—N2—C6—C5	−178.8 (4)	C8—C9—C10—C11	−53.9 (6)
C6—N2—C7—C8	101.0 (4)	C9—C10—C11—C12	54.0 (7)
C6—N2—C14—N1	0.1 (4)	C10—C11—C12—C13	−52.9 (7)
C14—N2—C6—C1	−0.6 (4)	C11—C12—C13—C8	53.0 (7)
C7—N2—C6—C5	−3.2 (6)	N1—C15—C16—C17	170.1 (3)
C17—N3—C24—C19	178.8 (3)	C15—C16—C17—N3	59.6 (4)
C18—N3—C24—C23	179.5 (3)	N4—C19—C24—N3	0.6 (4)
C18—N3—C17—C16	28.4 (4)	N4—C19—C24—C23	179.9 (3)
C24—N3—C17—C16	−151.7 (3)	N4—C19—C20—C21	−179.6 (3)
C18—N3—C24—C19	−1.3 (4)	C24—C19—C20—C21	−0.1 (5)
C17—N3—C18—N4	−178.5 (3)	C20—C19—C24—N3	−179.0 (3)
C24—N3—C18—N4	1.6 (4)	C20—C19—C24—C23	0.3 (5)
C17—N3—C24—C23	−0.4 (5)	C19—C20—C21—C22	0.1 (5)
C18—N4—C25—C26	103.4 (4)	C20—C21—C22—C23	−0.3 (6)
C18—N4—C19—C20	179.8 (4)	C21—C22—C23—C24	0.5 (5)
C19—N4—C25—C26	−76.3 (4)	C22—C23—C24—C19	−0.5 (5)
C25—N4—C18—N3	179.1 (3)	C22—C23—C24—N3	178.6 (3)
C25—N4—C19—C24	−179.9 (3)	N4—C25—C26—C27	−55.2 (4)
C25—N4—C19—C20	−0.4 (6)	N4—C25—C26—C31	−176.8 (3)
C19—N4—C18—N3	−1.2 (4)	C25—C26—C27—C28	−178.5 (4)
C18—N4—C19—C24	0.3 (4)	C31—C26—C27—C28	−57.0 (5)
N1—C1—C2—C3	−179.3 (4)	C25—C26—C31—C30	180.0 (3)
C2—C1—C6—C5	0.2 (6)	C27—C26—C31—C30	56.9 (4)
C2—C1—C6—N2	−178.2 (3)	C26—C27—C28—C29	56.8 (5)
N1—C1—C6—C5	179.2 (3)	C27—C28—C29—C30	−54.1 (5)
C6—C1—C2—C3	−0.6 (6)	C28—C29—C30—C31	52.9 (5)
N1—C1—C6—N2	0.9 (4)	C29—C30—C31—C26	−55.2 (5)

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y+1, −z+1; (iii) −x, −y, −z; (iv) −x+1, −y, −z; (v) −x+1, −y, −z+1; (vi) −x, −y, −z+1; (vii) x−1, y, z−1; (viii) −x+2, −y+1, −z+1; (ix) x−1, y, z; (x) x, y, z−1; (xi) −x+1, −y+1, −z; (xii) x, y, z+1; (xiii) −x+2, −y+1, −z+2; (xiv) x+1, y, z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···Br1	0.82 (3)	2.50 (3)	3.305 (5)	167 (3)
O1—H1B···Br2	0.82 (5)	2.60 (5)	3.421 (4)	173 (5)
C7—H7B···Br2	0.97	2.84	3.805 (5)	176
C18—H18···Br1	0.93	2.59	3.495 (4)	165
C27—H27B···N4	0.97	2.61	2.936 (5)	100