Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
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.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680602349X/lh2103sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680602349X/lh2103Isup2.hkl
Contains datablock I

CCDC reference: 618261

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 top

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 top
Crystal data top
C31H42N42+·2Br·H2OZ = 2
Mr = 648.50F(000) = 672
Triclinic, P1Dx = 1.434 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.2538 (5) ÅCell parameters from 42573 reflections
b = 12.5925 (8) Åθ = 1.9–28.0°
c = 15.4610 (9) ŵ = 2.73 mm1
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) Å3
Data collection top
STOE IPDS-II
diffractometer
5915 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus4567 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.049
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 1.9°
ω scansh = 1111
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 1515
Tmin = 0.258, Tmax = 0.440l = 1919
29924 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.110H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.047P)2 + 1.0857P]
where P = (Fo2 + 2Fc2)/3
5915 reflections(Δ/σ)max < 0.001
351 parametersΔρmax = 0.57 e Å3
3 restraintsΔρmin = 0.65 e Å3
Special details top

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 (Å2) top
xyzUiso*/Ueq
N10.1709 (3)0.1742 (2)0.18214 (19)0.0479 (8)
N20.3274 (3)0.1760 (2)0.0984 (2)0.0505 (9)
N30.1245 (3)0.2576 (2)0.46616 (18)0.0454 (8)
N40.2893 (3)0.2092 (3)0.56092 (18)0.0487 (8)
C10.0752 (4)0.1608 (3)0.0896 (2)0.0443 (9)
C20.0870 (4)0.1455 (3)0.0496 (3)0.0527 (11)
C30.1429 (5)0.1338 (3)0.0460 (3)0.0610 (12)
C40.0426 (5)0.1367 (3)0.0985 (3)0.0627 (13)
C50.1181 (5)0.1506 (3)0.0594 (2)0.0560 (11)
C60.1757 (4)0.1632 (3)0.0371 (2)0.0461 (10)
C70.4747 (5)0.1738 (4)0.0744 (3)0.0737 (17)
C80.6169 (5)0.3006 (4)0.1086 (3)0.0685 (14)
C90.5735 (6)0.3770 (4)0.0546 (3)0.0763 (17)
C100.7222 (6)0.5008 (5)0.0893 (4)0.0976 (19)
C110.7916 (7)0.5678 (5)0.1977 (4)0.107 (2)
C120.8348 (7)0.4949 (6)0.2533 (4)0.113 (2)
C130.6876 (6)0.3712 (5)0.2185 (3)0.0924 (19)
C140.3177 (4)0.1822 (3)0.1832 (2)0.0540 (11)
C150.1164 (4)0.1765 (3)0.2631 (2)0.0526 (11)
C160.1414 (4)0.3035 (3)0.3208 (2)0.0523 (11)
C170.0593 (5)0.3043 (3)0.3937 (2)0.0538 (11)
C180.2765 (4)0.2628 (3)0.4977 (2)0.0498 (10)
C190.1399 (4)0.1685 (3)0.5735 (2)0.0424 (9)
C200.0882 (4)0.1074 (3)0.6304 (2)0.0500 (10)
C210.0714 (5)0.0806 (3)0.6240 (2)0.0569 (11)
C220.1773 (5)0.1119 (3)0.5642 (3)0.0566 (12)
C230.1268 (4)0.1728 (3)0.5077 (2)0.0504 (11)
C240.0344 (4)0.2000 (3)0.5135 (2)0.0417 (9)
C250.4414 (4)0.1973 (3)0.6089 (2)0.0550 (11)
C260.5390 (4)0.2883 (3)0.7134 (2)0.0469 (10)
C270.5840 (5)0.4195 (3)0.7217 (3)0.0584 (11)
C280.6854 (5)0.5083 (3)0.8267 (3)0.0678 (14)
C290.8407 (5)0.4965 (3)0.8716 (3)0.0707 (12)
C300.8004 (5)0.3652 (4)0.8609 (3)0.0681 (12)
C310.6970 (4)0.2760 (3)0.7560 (3)0.0560 (11)
O10.4327 (4)0.0642 (4)0.3442 (3)0.0864 (16)
Br10.63098 (5)0.36704 (4)0.44457 (3)0.0749 (2)
Br20.64470 (5)0.00287 (4)0.20436 (3)0.0671 (1)
H20.154100.143400.085000.0640*
H30.251000.123600.076200.0730*
H40.085600.129000.162800.0750*
H50.184200.151400.095400.0670*
H7A0.436600.133300.004400.0880*
H7B0.516700.125800.104400.0880*
H80.707700.287800.094000.0820*
H9A0.480500.389400.064800.0920*
H9B0.538800.333500.014700.0920*
H10A0.809100.488600.070600.1170*
H10B0.687800.550300.057600.1170*
H11A0.891300.642800.216900.1280*
H11B0.710000.590600.214900.1280*
H12A0.867100.539400.322100.1350*
H12B0.929300.483300.244900.1350*
H13A0.599900.383100.236500.1110*
H13B0.722400.322700.251200.1110*
H140.403300.191100.236800.0650*
H15A0.179000.149600.306200.0630*
H15B0.001200.119500.237500.0630*
H16A0.095400.336100.275900.0630*
H16B0.260400.357100.355300.0630*
H17A0.078400.387500.427500.0650*
H17B0.060500.254200.359000.0650*
H180.361200.298700.478200.0600*
H200.157900.086000.670400.0600*
H210.110900.039800.661200.0680*
H220.285100.091100.562300.0680*
H230.196800.194400.468000.0600*
H25A0.512500.210100.572800.0660*
H25B0.409100.114800.607300.0660*
H260.470400.269300.750800.0560*
H27A0.648100.438500.682800.0700*
H27B0.482400.428100.696600.0700*
H28A0.715900.591400.829900.0810*
H28B0.616900.493700.864100.0810*
H29A0.896100.549900.940200.0850*
H29B0.916800.522300.840400.0850*
H30A0.903800.358400.884200.0820*
H30B0.739300.344000.900700.0820*
H31A0.763300.291000.717500.0670*
H31B0.667600.192900.752600.0670*
H1A0.478 (6)0.138 (2)0.377 (3)0.10 (2)*
H1B0.479 (5)0.041 (4)0.310 (3)0.091 (18)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0516 (16)0.0443 (14)0.0414 (14)0.0150 (12)0.0142 (12)0.0201 (12)
N20.0528 (16)0.0477 (15)0.0477 (15)0.0215 (13)0.0166 (13)0.0182 (12)
N30.0410 (14)0.0505 (15)0.0395 (14)0.0161 (12)0.0115 (11)0.0202 (12)
N40.0384 (14)0.0581 (16)0.0387 (14)0.0179 (12)0.0057 (11)0.0171 (12)
C10.0527 (18)0.0323 (14)0.0399 (16)0.0152 (13)0.0118 (14)0.0139 (12)
C20.054 (2)0.0455 (18)0.054 (2)0.0216 (15)0.0158 (16)0.0187 (15)
C30.059 (2)0.055 (2)0.056 (2)0.0275 (17)0.0042 (18)0.0185 (17)
C40.080 (3)0.058 (2)0.0386 (18)0.0320 (19)0.0086 (18)0.0152 (16)
C50.076 (2)0.0466 (18)0.0450 (18)0.0278 (17)0.0226 (18)0.0175 (15)
C60.0574 (19)0.0345 (15)0.0420 (17)0.0193 (14)0.0148 (15)0.0147 (13)
C70.081 (3)0.071 (3)0.072 (3)0.042 (2)0.025 (2)0.026 (2)
C80.065 (2)0.080 (3)0.069 (2)0.040 (2)0.029 (2)0.028 (2)
C90.076 (3)0.081 (3)0.083 (3)0.042 (2)0.034 (2)0.036 (2)
C100.078 (3)0.092 (3)0.118 (4)0.029 (3)0.040 (3)0.044 (3)
C110.080 (3)0.089 (4)0.112 (4)0.012 (3)0.046 (3)0.004 (3)
C120.075 (3)0.131 (5)0.085 (4)0.012 (3)0.032 (3)0.017 (3)
C130.082 (3)0.112 (4)0.064 (3)0.031 (3)0.023 (2)0.028 (3)
C140.054 (2)0.0524 (19)0.0468 (19)0.0185 (16)0.0117 (16)0.0216 (15)
C150.059 (2)0.0484 (18)0.0449 (18)0.0148 (15)0.0187 (16)0.0239 (15)
C160.060 (2)0.0462 (18)0.0454 (18)0.0175 (15)0.0159 (16)0.0233 (15)
C170.055 (2)0.060 (2)0.0481 (19)0.0266 (17)0.0150 (16)0.0277 (16)
C180.0378 (16)0.061 (2)0.0415 (17)0.0141 (14)0.0104 (14)0.0227 (15)
C190.0391 (16)0.0421 (16)0.0348 (15)0.0131 (13)0.0099 (13)0.0101 (12)
C200.060 (2)0.0441 (17)0.0383 (16)0.0199 (15)0.0145 (15)0.0142 (13)
C210.071 (2)0.0529 (19)0.0455 (19)0.0203 (17)0.0302 (18)0.0194 (15)
C220.053 (2)0.056 (2)0.057 (2)0.0192 (16)0.0292 (17)0.0152 (17)
C230.0442 (18)0.0541 (19)0.0468 (18)0.0222 (15)0.0134 (15)0.0148 (15)
C240.0405 (16)0.0405 (15)0.0345 (15)0.0131 (13)0.0109 (13)0.0110 (12)
C250.0458 (18)0.059 (2)0.0480 (19)0.0246 (16)0.0072 (15)0.0126 (16)
C260.0418 (17)0.0479 (17)0.0439 (17)0.0182 (14)0.0112 (14)0.0156 (14)
C270.064 (2)0.0518 (19)0.056 (2)0.0281 (17)0.0163 (18)0.0202 (16)
C280.070 (3)0.050 (2)0.067 (2)0.0229 (18)0.019 (2)0.0119 (18)
C290.059 (2)0.057 (2)0.063 (2)0.0140 (18)0.0089 (19)0.0058 (18)
C300.055 (2)0.068 (2)0.059 (2)0.0223 (18)0.0022 (18)0.0196 (19)
C310.0502 (19)0.0517 (19)0.056 (2)0.0237 (16)0.0087 (16)0.0172 (16)
O10.075 (2)0.088 (3)0.104 (3)0.033 (2)0.045 (2)0.043 (2)
Br10.0603 (2)0.0779 (3)0.0715 (3)0.0206 (2)0.0283 (2)0.0181 (2)
Br20.0622 (2)0.0797 (3)0.0644 (2)0.0346 (2)0.0226 (2)0.0338 (2)
Geometric parameters (Å, º) top
O1—H1A0.82 (3)C2—H20.9300
O1—H1B0.82 (5)C3—H30.9300
N1—C11.397 (4)C4—H40.9300
N1—C141.323 (5)C5—H50.9300
N1—C151.467 (4)C7—H7B0.9700
N2—C61.395 (5)C7—H7A0.9700
N2—C141.322 (4)C8—H80.9800
N2—C71.513 (6)C9—H9A0.9700
N3—C181.331 (5)C9—H9B0.9700
N3—C241.395 (5)C10—H10B0.9700
N3—C171.479 (4)C10—H10A0.9700
N4—C251.482 (5)C11—H11B0.9700
N4—C181.327 (5)C11—H11A0.9700
N4—C191.387 (5)C12—H12A0.9700
C1—C61.387 (5)C12—H12B0.9700
C1—C21.383 (6)C13—H13B0.9700
C2—C31.378 (6)C13—H13A0.9700
C3—C41.385 (7)C14—H140.9300
C4—C51.375 (7)C15—H15B0.9700
C5—C61.388 (4)C15—H15A0.9700
C7—C81.519 (7)C16—H16B0.9700
C8—C131.525 (6)C16—H16A0.9700
C8—C91.512 (7)C17—H17B0.9700
C9—C101.520 (8)C17—H17A0.9700
C10—C111.500 (8)C18—H180.9300
C11—C121.489 (9)C20—H200.9300
C12—C131.513 (9)C21—H210.9300
C15—C161.517 (5)C22—H220.9300
C16—C171.519 (5)C23—H230.9300
C19—C241.393 (5)C25—H25B0.9700
C19—C201.386 (5)C25—H25A0.9700
C20—C211.367 (6)C26—H260.9800
C21—C221.392 (6)C27—H27A0.9700
C22—C231.375 (5)C27—H27B0.9700
C23—C241.383 (6)C28—H28A0.9700
C25—C261.511 (4)C28—H28B0.9700
C26—C311.512 (6)C29—H29B0.9700
C26—C271.520 (5)C29—H29A0.9700
C27—C281.512 (6)C30—H30A0.9700
C28—C291.494 (7)C30—H30B0.9700
C29—C301.517 (6)C31—H31B0.9700
C30—C311.514 (6)C31—H31A0.9700
Br1···C133.682 (5)H7A···H52.5500
Br1···C183.495 (4)H7A···H9B2.5000
Br1···O13.305 (5)H7B···Br22.8400
Br2···O13.421 (4)H7B···H13B2.5400
Br1···H13A3.2200H8···H2i2.5500
Br1···H143.0200H8···H10A2.5400
Br1···H23i3.1400H8···H12B2.5900
Br1···H17Aii2.9900H9A···C63.0800
Br1···H182.5900H9A···N22.8300
Br1···H1A2.50 (3)H9A···H10Bxi2.5600
Br2···H7B2.8400H9A···H28Bii2.1900
Br2···H15Bi2.9300H9A···C28ii2.9100
Br2···H17Bi3.1700H9B···H30Bx2.5300
Br2···H3iii3.2000H9B···H7A2.5000
Br2···H7Aiv2.9600H10A···H29Ax2.5600
Br2···H20v2.9400H10A···H82.5400
Br2···H1B2.60 (5)H10A···C29viii3.0500
O1···Br23.421 (4)H10A···H30Aviii2.4600
O1···C143.334 (6)H10A···H30Bx2.5400
O1···Br13.305 (5)H10B···H9Axi2.5600
O1···H21vi2.7800H11B···H27Bii2.5100
O1···H22vi2.9100H12B···H82.5900
O1···H142.6100H12B···H29Bviii2.1900
O1···H15A2.8900H13A···Br13.2200
O1···H31Bv2.8700H13A···C142.6700
N1···N22.185 (4)H13A···H142.4800
N1···C4iii3.431 (5)H13A···N22.7300
N2···N12.185 (4)H13B···H7B2.5400
N2···C3iii3.441 (5)H14···O12.6100
N1···H28Aii2.8500H14···C132.9600
N2···H9A2.8300H14···Br13.0200
N2···H13A2.7300H14···H13A2.4800
N3···H15A2.7600H14···H15A2.5500
N4···H27B2.6100H14···H1A2.4300
C1···C5iii3.548 (5)H15A···H182.5000
C1···C6iii3.576 (5)H15A···H21vi2.4700
C2···C6iii3.478 (5)H15A···O12.8900
C3···N2iii3.441 (5)H15A···N32.7600
C3···C14iii3.509 (5)H15A···C182.6700
C4···C14iii3.577 (5)H15A···H142.5500
C4···N1iii3.431 (5)H15B···Br2ix2.9300
C5···C1iii3.548 (5)H15B···C22.9300
C6···C2iii3.478 (5)H15B···H22.5500
C6···C1iii3.576 (5)H15B···H17B2.5000
C13···C143.228 (7)H16A···C13.0500
C13···Br13.682 (5)H16B···C182.7500
C14···C133.228 (7)H16B···H182.2900
C14···C3iii3.509 (5)H17A···Br1ii2.9900
C14···O13.334 (6)H17B···Br2ix3.1700
C14···C4iii3.577 (5)H17B···C232.8700
C15···C183.239 (4)H17B···H232.4800
C18···C153.239 (4)H17B···H15B2.5000
C18···C273.360 (5)H18···C153.0800
C18···Br13.495 (4)H18···C162.7500
C19···C20vi3.489 (4)H18···Br12.5900
C19···C21vi3.491 (5)H18···H15A2.5000
C20···C19vi3.489 (4)H18···H16B2.2900
C20···C24vi3.519 (5)H18···H25A2.4800
C21···C19vi3.491 (5)H20···Br2v2.9400
C22···C25vi3.584 (5)H20···C253.0400
C24···C20vi3.519 (5)H21···H4xii2.5700
C25···C22vi3.584 (5)H21···O1vi2.7800
C27···C183.360 (5)H21···H15Avi2.4700
C1···H16A3.0500H22···O1vi2.9100
C1···H28Aii2.7500H23···Br1ix3.1400
C2···H15B2.9300H23···H17B2.4800
C4···H30Avii3.0600H23···C172.9800
C5···H7A2.9500H25A···H27A2.5600
C6···H28Aii2.8700H25A···H182.4800
C6···H9A3.0800H25A···H31A2.4200
C7···H53.0800H25B···H31B2.4700
C9···H28Bii3.0700H25B···C203.0600
C12···H29Bviii3.0700H25B···C22vi2.9300
C13···H142.9600H26···C193.0800
C14···H13A2.6700H26···H28B2.5300
C14···H28Aii3.0200H26···H30B2.5700
C15···H23.0000H27A···H31A2.5400
C15···H183.0800H27A···H25A2.5600
C16···H182.7500H27B···N42.6100
C17···H232.9800H27B···H11Bii2.5100
C18···H16B2.7500H27B···C182.8700
C18···H15A2.6700H28A···N1ii2.8500
C18···H27B2.8700H28A···C14ii3.0200
C19···H263.0800H28A···C1ii2.7500
C20···H25B3.0600H28A···C6ii2.8700
C22···H25Bvi2.9300H28B···C9ii3.0700
C23···H17B2.8700H28B···H262.5300
C25···H203.0400H28B···H9Aii2.1900
C28···H9Aii2.9100H29A···H10Axii2.5600
C29···H10Aviii3.0500H29A···H30Axiii2.5200
H1A···H142.4300H29B···H12Bviii2.1900
H1A···Br12.50 (3)H29B···C12viii3.0700
H1B···H31Bv2.5600H30A···H10Aviii2.4600
H1B···Br22.60 (5)H30A···C4xiv3.0600
H2···H15B2.5500H30A···H29Axiii2.5200
H2···C153.0000H30B···H9Bxii2.5300
H2···H8ix2.5500H30B···H10Axii2.5400
H3···Br2iii3.2000H30B···H262.5700
H4···H21x2.5700H31A···H27A2.5400
H5···C73.0800H31A···H25A2.4200
H5···H7A2.5500H31B···H1Bv2.5600
H7A···Br2iv2.9600H31B···O1v2.8700
H7A···C52.9500H31B···H25B2.4700
H1A—O1—H1B115 (5)C11—C10—H10B109.00
C1—N1—C15125.8 (3)H10A—C10—H10B108.00
C14—N1—C15126.2 (3)C11—C10—H10A109.00
C1—N1—C14108.0 (3)C10—C11—H11A109.00
C6—N2—C7128.4 (3)C10—C11—H11B109.00
C7—N2—C14124.1 (3)C12—C11—H11B109.00
C6—N2—C14107.4 (3)H11A—C11—H11B108.00
C17—N3—C18126.8 (3)C12—C11—H11A109.00
C18—N3—C24108.3 (3)C11—C12—H12B109.00
C17—N3—C24124.9 (3)C13—C12—H12A110.00
C18—N4—C19108.9 (3)C13—C12—H12B109.00
C18—N4—C25124.0 (3)H12A—C12—H12B108.00
C19—N4—C25127.1 (3)C11—C12—H12A109.00
N1—C1—C2131.4 (3)C8—C13—H13A109.00
N1—C1—C6106.1 (3)C8—C13—H13B109.00
C2—C1—C6122.5 (3)C12—C13—H13B109.00
C1—C2—C3115.8 (4)H13A—C13—H13B108.00
C2—C3—C4121.8 (4)C12—C13—H13A109.00
C3—C4—C5122.6 (4)N2—C14—H14124.00
C4—C5—C6115.9 (4)N1—C14—H14124.00
N2—C6—C5131.5 (4)N1—C15—H15A109.00
C1—C6—C5121.3 (4)N1—C15—H15B109.00
N2—C6—C1107.2 (3)C16—C15—H15B109.00
N2—C7—C8113.5 (4)H15A—C15—H15B108.00
C7—C8—C13112.9 (4)C16—C15—H15A109.00
C9—C8—C13110.9 (4)C15—C16—H16B109.00
C7—C8—C9113.6 (4)C17—C16—H16A109.00
C8—C9—C10111.2 (4)C17—C16—H16B109.00
C9—C10—C11111.9 (5)H16A—C16—H16B108.00
C10—C11—C12113.5 (5)C15—C16—H16A109.00
C11—C12—C13110.8 (5)N3—C17—H17A109.00
C8—C13—C12112.9 (4)N3—C17—H17B109.00
N1—C14—N2111.4 (3)C16—C17—H17B109.00
N1—C15—C16112.1 (3)H17A—C17—H17B108.00
C15—C16—C17113.1 (3)C16—C17—H17A109.00
N3—C17—C16112.5 (4)N3—C18—H18125.00
N3—C18—N4110.1 (3)N4—C18—H18125.00
N4—C19—C20132.0 (3)C21—C20—H20122.00
C20—C19—C24121.6 (4)C19—C20—H20122.00
N4—C19—C24106.4 (3)C20—C21—H21119.00
C19—C20—C21115.9 (3)C22—C21—H21119.00
C20—C21—C22122.7 (4)C23—C22—H22119.00
C21—C22—C23121.7 (4)C21—C22—H22119.00
C22—C23—C24116.0 (4)C22—C23—H23122.00
N3—C24—C19106.4 (3)C24—C23—H23122.00
C19—C24—C23122.1 (3)N4—C25—H25A109.00
N3—C24—C23131.6 (3)N4—C25—H25B109.00
N4—C25—C26112.1 (3)C26—C25—H25B109.00
C25—C26—C31109.3 (3)H25A—C25—H25B108.00
C27—C26—C31109.6 (3)C26—C25—H25A109.00
C25—C26—C27112.0 (3)C27—C26—H26109.00
C26—C27—C28110.6 (3)C31—C26—H26109.00
C27—C28—C29112.5 (4)C25—C26—H26109.00
C28—C29—C30111.1 (4)C26—C27—H27B110.00
C29—C30—C31111.7 (4)C28—C27—H27A110.00
C26—C31—C30111.7 (3)C26—C27—H27A110.00
C3—C2—H2122.00H27A—C27—H27B108.00
C1—C2—H2122.00C28—C27—H27B110.00
C2—C3—H3119.00C27—C28—H28A109.00
C4—C3—H3119.00C27—C28—H28B109.00
C5—C4—H4119.00C29—C28—H28B109.00
C3—C4—H4119.00H28A—C28—H28B108.00
C4—C5—H5122.00C29—C28—H28A109.00
C6—C5—H5122.00C28—C29—H29B109.00
N2—C7—H7B109.00C30—C29—H29A109.00
C8—C7—H7A109.00C30—C29—H29B109.00
C8—C7—H7B109.00H29A—C29—H29B108.00
H7A—C7—H7B108.00C28—C29—H29A109.00
N2—C7—H7A109.00C29—C30—H30B109.00
C9—C8—H8106.00C31—C30—H30A109.00
C13—C8—H8106.00C29—C30—H30A109.00
C7—C8—H8106.00H30A—C30—H30B108.00
C8—C9—H9B109.00C31—C30—H30B109.00
C10—C9—H9A109.00C26—C31—H31A109.00
C10—C9—H9B109.00C26—C31—H31B109.00
H9A—C9—H9B108.00C30—C31—H31B109.00
C8—C9—H9A109.00H31A—C31—H31B108.00
C9—C10—H10A109.00C30—C31—H31A109.00
C9—C10—H10B109.00
C14—N1—C1—C2178.1 (4)C1—C2—C3—C40.3 (6)
C15—N1—C1—C20.8 (6)C2—C3—C4—C50.4 (6)
C14—N1—C1—C60.8 (4)C3—C4—C5—C60.8 (6)
C15—N1—C1—C6179.7 (3)C4—C5—C6—C10.5 (5)
C1—N1—C15—C1684.7 (4)C4—C5—C6—N2178.4 (4)
C14—N1—C15—C1696.7 (4)N2—C7—C8—C967.7 (5)
C1—N1—C14—N20.5 (4)N2—C7—C8—C1359.5 (5)
C15—N1—C14—N2179.3 (3)C7—C8—C13—C12177.1 (5)
C7—N2—C6—C1174.9 (4)C7—C8—C9—C10177.9 (4)
C14—N2—C7—C884.1 (5)C13—C8—C9—C1053.8 (6)
C7—N2—C14—N1175.7 (3)C9—C8—C13—C1254.2 (6)
C14—N2—C6—C5178.8 (4)C8—C9—C10—C1153.9 (6)
C6—N2—C7—C8101.0 (4)C9—C10—C11—C1254.0 (7)
C6—N2—C14—N10.1 (4)C10—C11—C12—C1352.9 (7)
C14—N2—C6—C10.6 (4)C11—C12—C13—C853.0 (7)
C7—N2—C6—C53.2 (6)N1—C15—C16—C17170.1 (3)
C17—N3—C24—C19178.8 (3)C15—C16—C17—N359.6 (4)
C18—N3—C24—C23179.5 (3)N4—C19—C24—N30.6 (4)
C18—N3—C17—C1628.4 (4)N4—C19—C24—C23179.9 (3)
C24—N3—C17—C16151.7 (3)N4—C19—C20—C21179.6 (3)
C18—N3—C24—C191.3 (4)C24—C19—C20—C210.1 (5)
C17—N3—C18—N4178.5 (3)C20—C19—C24—N3179.0 (3)
C24—N3—C18—N41.6 (4)C20—C19—C24—C230.3 (5)
C17—N3—C24—C230.4 (5)C19—C20—C21—C220.1 (5)
C18—N4—C25—C26103.4 (4)C20—C21—C22—C230.3 (6)
C18—N4—C19—C20179.8 (4)C21—C22—C23—C240.5 (5)
C19—N4—C25—C2676.3 (4)C22—C23—C24—C190.5 (5)
C25—N4—C18—N3179.1 (3)C22—C23—C24—N3178.6 (3)
C25—N4—C19—C24179.9 (3)N4—C25—C26—C2755.2 (4)
C25—N4—C19—C200.4 (6)N4—C25—C26—C31176.8 (3)
C19—N4—C18—N31.2 (4)C25—C26—C27—C28178.5 (4)
C18—N4—C19—C240.3 (4)C31—C26—C27—C2857.0 (5)
N1—C1—C2—C3179.3 (4)C25—C26—C31—C30180.0 (3)
C2—C1—C6—C50.2 (6)C27—C26—C31—C3056.9 (4)
C2—C1—C6—N2178.2 (3)C26—C27—C28—C2956.8 (5)
N1—C1—C6—C5179.2 (3)C27—C28—C29—C3054.1 (5)
C6—C1—C2—C30.6 (6)C28—C29—C30—C3152.9 (5)
N1—C1—C6—N20.9 (4)C29—C30—C31—C2655.2 (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) x1, y, z1; (viii) x+2, y+1, z+1; (ix) x1, y, z; (x) x, y, z1; (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) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···Br10.82 (3)2.50 (3)3.305 (5)167 (3)
O1—H1B···Br20.82 (5)2.60 (5)3.421 (4)173 (5)
C7—H7B···Br20.972.843.805 (5)176
C18—H18···Br10.932.593.495 (4)165
C27—H27B···N40.972.612.936 (5)100
 

Subscribe to Acta Crystallographica Section E: Crystallographic Communications

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds