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The title compound, C27H34N42+·2Br·H2O, was synthesized from 1,1′-propyl­endibenzimidazole and 1-bromo-3-methyl­but-2-ene in dimethyl­formamide solution. The compound crystallizes with one water mol­ecule and two Br ions in the asymmetric unit. The crystal structure is stabilized by inter- and intra­molecular O—H...Br and C—H...Br hydrogen-bonding inter­actions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806028297/hg2067sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806028297/hg2067Isup2.hkl
Contains datablock I

CCDC reference: 618221

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.006 Å
  • R factor = 0.038
  • wR factor = 0.093
  • Data-to-parameter ratio = 16.6

checkCIF/PLATON results

No syntax errors found



Alert level A PLAT220_ALERT_2_A Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.99 Ratio PLAT222_ALERT_3_A Large Non-Solvent H Ueq(max)/Ueq(min) ... 5.75 Ratio PLAT242_ALERT_2_A Check Low Ueq as Compared to Neighbors for C25
Alert level B PLAT230_ALERT_2_B Hirshfeld Test Diff for C23 - C24 .. 7.01 su PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C10
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.62 mm
3 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 3 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 4 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

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: SIR97 (Altomare et al., 1999); 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(3-methylbut-2-enyl)-1,1'-propylenedibenzimidazolium dibromide monohydrate top
Crystal data top
C27H34N42+·2Br·H2OZ = 2
Mr = 592.40F(000) = 608
Triclinic, P1Dx = 1.423 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.7777 (4) ÅCell parameters from 29997 reflections
b = 12.0851 (7) Åθ = 2.5–28.0°
c = 14.4078 (7) ŵ = 2.96 mm1
α = 106.966 (4)°T = 296 K
β = 96.868 (4)°Prism, colourless
γ = 104.747 (4)°0.62 × 0.49 × 0.32 mm
V = 1382.30 (13) Å3
Data collection top
Stoe IPDSII
diffractometer
5267 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long fine-focus4128 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.063
Detector resolution: 6.67 pixels mm-1θmax = 26.0°, θmin = 2.5°
ω scansh = 1010
Absorption correction: integration
(X-RED32; Stoe & Cie, 2002)
k = 1414
Tmin = 0.261, Tmax = 0.451l = 1717
25534 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)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0473P)2 + 0.3788P]
where P = (Fo2 + 2Fc2)/3
5267 reflections(Δ/σ)max = 0.001
317 parametersΔρmax = 0.54 e Å3
0 restraintsΔρmin = 0.33 e Å3
Special details top

Experimental. Spectroscopic analysis: 1H NMR (DMSO-d6, δ, p.p.m.): 1.79 (d, CH3, 6H), 1.88 (d, CH3, 6H), 2.71 (m, bridge methylene, 2H), 4.82 (t, bridge methylene, 4H), 5.11 (d, NCH2, 4H), 5.50 (t, CH, 2H), 7.71–8.32 (m, Ar—H, 8H), 10.01 (s, 2-CH, 2H); 13C NMR (DMSO-d6, δ, p.p.m.): 18.72, 22.48, 25.99, 28.90, 36.70, 44.44, 45.31, 114.30, 116.77, 127.02, 131.44, 131.77, 141.01, 142.48. Analysis calculated for C27H36N4Br2O: C 54.73, H 6.08, N 9.46%; found: C 54.84, H 6.09, N 9.60%.

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
N10.5147 (3)0.5094 (2)0.19051 (17)0.0439 (7)
N20.2696 (3)0.4121 (2)0.10640 (17)0.0465 (7)
N30.8561 (3)0.7182 (2)0.48086 (17)0.0447 (7)
N40.7582 (3)0.8499 (3)0.57274 (18)0.0550 (9)
C10.5273 (3)0.4326 (3)0.1007 (2)0.0450 (8)
C20.6607 (4)0.4136 (3)0.0623 (2)0.0537 (10)
C30.6285 (4)0.3297 (3)0.0310 (3)0.0646 (11)
C40.4708 (5)0.2665 (3)0.0845 (2)0.0669 (11)
C50.3388 (4)0.2859 (3)0.0476 (2)0.0581 (10)
C60.3706 (3)0.3699 (3)0.0476 (2)0.0464 (9)
C70.3596 (3)0.4947 (3)0.1903 (2)0.0472 (8)
C80.0905 (4)0.3725 (3)0.0805 (2)0.0563 (10)
C90.0204 (4)0.2460 (3)0.0776 (3)0.0677 (11)
C100.0267 (5)0.2126 (4)0.1527 (3)0.0823 (16)
C110.0923 (8)0.0812 (6)0.1421 (5)0.128 (3)
C120.0117 (10)0.2998 (7)0.2519 (4)0.149 (3)
C130.6499 (3)0.5937 (3)0.2704 (2)0.0470 (8)
C140.7111 (4)0.5303 (3)0.3372 (2)0.0497 (9)
C150.8681 (4)0.6067 (3)0.4104 (2)0.0514 (9)
C160.9840 (3)0.8235 (3)0.5294 (2)0.0431 (8)
C171.1470 (3)0.8504 (3)0.5273 (3)0.0551 (10)
C181.2414 (4)0.9662 (3)0.5853 (3)0.0651 (11)
C191.1787 (4)1.0497 (3)0.6411 (3)0.0646 (11)
C201.0192 (4)1.0244 (3)0.6438 (2)0.0601 (11)
C210.9222 (3)0.9078 (3)0.5871 (2)0.0472 (9)
C220.7243 (3)0.7377 (3)0.5100 (2)0.0523 (9)
C230.6374 (5)0.9079 (5)0.6137 (3)0.0763 (14)
C240.6703 (6)0.9618 (4)0.7220 (4)0.0850 (16)
C250.6083 (5)0.9017 (4)0.7841 (3)0.0736 (12)
C260.6463 (9)0.9612 (7)0.8888 (4)0.139 (3)
C270.5209 (14)0.7702 (8)0.7420 (6)0.215 (5)
O10.4199 (3)0.7949 (3)0.3473 (3)0.0804 (10)
Br10.31028 (4)0.57545 (3)0.44246 (2)0.0606 (1)
Br21.05482 (4)0.68991 (3)0.19576 (2)0.0577 (1)
H20.765600.455400.098000.0640*
H30.714000.314400.059500.0770*
H40.454700.209500.147100.0800*
H50.234200.245100.084100.0700*
H70.319800.536700.241900.0570*
H8A0.051000.426400.129000.0670*
H8B0.055600.378500.016100.0670*
H90.008000.184400.018200.0810*
H11A0.126000.033100.072900.1910*
H11B0.182800.070200.173500.1910*
H11C0.010200.056200.173000.1910*
H12A0.068600.291900.298800.2240*
H12B0.113300.283500.271800.2240*
H12C0.019400.381000.249600.2240*
H13A0.615800.659400.309800.0560*
H13B0.736800.628500.241900.0560*
H14A0.629500.507700.373800.0600*
H14B0.726000.456200.295900.0600*
H15A0.902000.558500.447200.0620*
H15B0.950300.628500.373900.0620*
H171.189600.794100.489200.0660*
H181.351400.988400.586600.0780*
H191.247801.126600.678500.0770*
H200.977701.081900.681500.0720*
H220.622500.680600.489300.0630*
H23A0.632000.970700.585300.0920*
H23B0.532400.847000.591900.0920*
H240.737101.041500.750900.1020*
H26A0.758400.975200.913700.2080*
H26B0.582200.911000.919500.2080*
H26C0.623801.037500.903700.2080*
H27A0.407000.758200.731000.3220*
H27B0.549400.730800.787500.3220*
H27C0.549800.736200.680100.3220*
H1A0.396 (6)0.769 (5)0.390 (4)0.0870*
H1B0.333 (6)0.779 (4)0.310 (4)0.0870*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0405 (12)0.0429 (12)0.0404 (12)0.0054 (9)0.0087 (9)0.0089 (10)
N20.0415 (12)0.0485 (13)0.0431 (12)0.0097 (10)0.0082 (10)0.0096 (10)
N30.0377 (11)0.0508 (13)0.0408 (12)0.0093 (10)0.0075 (9)0.0125 (10)
N40.0440 (13)0.0729 (18)0.0441 (13)0.0181 (12)0.0116 (11)0.0127 (12)
C10.0473 (15)0.0443 (15)0.0404 (14)0.0107 (12)0.0102 (12)0.0123 (11)
C20.0480 (16)0.0590 (18)0.0514 (17)0.0131 (14)0.0144 (13)0.0157 (14)
C30.066 (2)0.071 (2)0.0579 (19)0.0267 (17)0.0260 (17)0.0131 (16)
C40.075 (2)0.071 (2)0.0439 (17)0.0244 (18)0.0125 (16)0.0018 (15)
C50.0603 (18)0.0594 (19)0.0396 (15)0.0121 (15)0.0018 (13)0.0034 (13)
C60.0468 (15)0.0454 (15)0.0432 (15)0.0132 (12)0.0073 (12)0.0111 (12)
C70.0473 (15)0.0474 (15)0.0417 (14)0.0104 (12)0.0114 (12)0.0102 (12)
C80.0417 (15)0.067 (2)0.0548 (18)0.0132 (14)0.0066 (13)0.0168 (15)
C90.0555 (18)0.065 (2)0.063 (2)0.0018 (16)0.0087 (16)0.0087 (17)
C100.065 (2)0.087 (3)0.082 (3)0.002 (2)0.0012 (19)0.037 (2)
C110.128 (5)0.113 (4)0.129 (5)0.007 (4)0.005 (4)0.067 (4)
C120.196 (7)0.140 (6)0.083 (4)0.005 (5)0.050 (4)0.036 (4)
C130.0466 (15)0.0415 (14)0.0412 (14)0.0023 (12)0.0062 (12)0.0076 (11)
C140.0501 (15)0.0406 (15)0.0488 (16)0.0054 (12)0.0047 (13)0.0106 (12)
C150.0458 (15)0.0514 (17)0.0506 (16)0.0140 (13)0.0055 (12)0.0101 (13)
C160.0392 (13)0.0466 (15)0.0408 (14)0.0105 (11)0.0034 (11)0.0148 (12)
C170.0383 (14)0.0587 (18)0.068 (2)0.0146 (13)0.0087 (14)0.0221 (15)
C180.0434 (16)0.064 (2)0.082 (2)0.0070 (15)0.0020 (16)0.0286 (18)
C190.0583 (19)0.0508 (18)0.070 (2)0.0030 (15)0.0087 (16)0.0193 (16)
C200.069 (2)0.0555 (18)0.0493 (17)0.0202 (16)0.0018 (15)0.0112 (14)
C210.0460 (15)0.0545 (17)0.0412 (14)0.0166 (13)0.0059 (12)0.0166 (12)
C220.0393 (14)0.0673 (19)0.0426 (15)0.0087 (13)0.0104 (12)0.0129 (14)
C230.064 (2)0.105 (3)0.063 (2)0.041 (2)0.0229 (18)0.016 (2)
C240.089 (3)0.065 (2)0.090 (3)0.013 (2)0.031 (2)0.014 (2)
C250.080 (2)0.061 (2)0.067 (2)0.0087 (18)0.0046 (19)0.0183 (18)
C260.148 (6)0.158 (6)0.087 (4)0.032 (5)0.033 (4)0.017 (4)
C270.308 (12)0.123 (6)0.123 (6)0.072 (7)0.035 (7)0.032 (5)
O10.0546 (14)0.0775 (18)0.098 (2)0.0044 (13)0.0064 (14)0.0305 (16)
Br10.0486 (2)0.0792 (2)0.0579 (2)0.0162 (2)0.0131 (1)0.0308 (2)
Br20.0486 (2)0.0633 (2)0.0529 (2)0.0133 (1)0.0123 (1)0.0100 (1)
Geometric parameters (Å, º) top
O1—H1B0.82 (5)C25—C261.424 (7)
O1—H1A0.79 (6)C2—H20.9300
N1—C71.327 (4)C3—H30.9300
N1—C11.391 (4)C4—H40.9300
N1—C131.464 (4)C5—H50.9300
N2—C71.322 (4)C7—H70.9300
N2—C61.386 (4)C8—H8A0.9700
N2—C81.487 (4)C8—H8B0.9700
N3—C221.330 (4)C9—H90.9300
N3—C151.469 (4)C11—H11A0.9600
N3—C161.391 (4)C11—H11B0.9600
N4—C221.326 (5)C11—H11C0.9600
N4—C231.500 (6)C12—H12A0.9600
N4—C211.392 (4)C12—H12C0.9600
C1—C21.396 (5)C12—H12B0.9600
C1—C61.390 (4)C13—H13B0.9700
C2—C31.372 (5)C13—H13A0.9700
C3—C41.399 (6)C14—H14A0.9700
C4—C51.376 (6)C14—H14B0.9700
C5—C61.393 (4)C15—H15A0.9700
C8—C91.482 (5)C15—H15B0.9700
C9—C101.335 (6)C17—H170.9300
C10—C121.475 (7)C18—H180.9300
C10—C111.500 (9)C19—H190.9300
C13—C141.523 (5)C20—H200.9300
C14—C151.517 (5)C22—H220.9300
C16—C211.385 (4)C23—H23B0.9700
C16—C171.390 (4)C23—H23A0.9700
C17—C181.380 (5)C24—H240.9300
C18—C191.372 (5)C26—H26B0.9600
C19—C201.363 (5)C26—H26C0.9600
C20—C211.389 (5)C26—H26A0.9600
C23—C241.465 (7)C27—H27C0.9600
C24—C251.385 (7)C27—H27A0.9600
C25—C271.479 (11)C27—H27B0.9600
Br1···C223.523 (3)H2···Br23.1000
Br1···O13.313 (4)H2···C133.0100
Br1···C15i3.682 (3)H2···H13B2.5700
Br1···C73.586 (3)H3···Br2vi2.9900
Br2···O1ii3.360 (3)H5···C83.0300
Br1···H222.6200H5···Br2v3.2300
Br1···H17iii3.0200H7···Br12.8000
Br1···H1A2.62 (6)H7···O12.8900
Br1···H72.8000H7···H8A2.4900
Br1···H14Ai3.1300H7···H13A2.5500
Br1···H15Ai3.0500H8A···Br2iii3.0400
Br2···H15B3.0500H8A···C122.6800
Br2···H13B2.9100H8A···H72.4900
Br2···H1Bii2.55 (5)H8A···H12C2.0000
Br2···H23.1000H8B···Br2v2.8900
Br2···H8Aii3.0400H9···H11A2.3100
Br2···H24iv3.1100H11A···C26ix2.8800
Br2···H5v3.2300H11A···H92.3100
Br2···H8Bv2.8900H11A···H26Aix2.2200
Br2···H3vi2.9900H11B···H12B2.4300
Br2···H20iv2.9100H11C···C20i3.0700
O1···Br2iii3.360 (3)H12B···H11B2.4300
O1···C18iv3.380 (5)H12B···H27Ax2.4900
O1···Br13.313 (4)H12C···C82.5700
O1···H72.8900H12C···H8A2.0000
O1···H18iv2.6800H13A···H19iv2.5000
O1···H13A2.6600H13A···O12.6600
O1···H23Avii2.8900H13A···N32.8300
N1···N22.176 (4)H13A···C222.7200
N2···N12.176 (4)H13A···H72.5500
N3···N42.182 (4)H13A···H222.5200
N4···N32.182 (4)H13B···H22.5700
N1···H27Bi2.9300H13B···Br22.9100
N3···H13A2.8300H13B···C22.9400
N4···H27C2.8700H13B···H15B2.5100
C2···C6v3.480 (5)H14A···Br1i3.1300
C3···C7v3.545 (5)H14A···C222.7400
C5···C93.511 (5)H14A···H222.2800
C6···C2v3.480 (5)H14B···C13.0200
C7···Br13.586 (3)H14B···C27i2.8800
C7···C3v3.545 (5)H14B···H27Ai2.4500
C9···C53.511 (5)H15A···Br1i3.0500
C13···C223.278 (4)H15B···H172.5000
C14···C27i3.449 (11)H15B···Br23.0500
C15···Br1i3.682 (3)H15B···C172.8900
C16···C20iv3.506 (5)H15B···H13B2.5100
C16···C19iv3.591 (5)H17···H1Aii2.4600
C17···C20iv3.597 (5)H17···Br1ii3.0200
C18···O1iv3.380 (5)H17···C152.9800
C19···C21iv3.518 (5)H17···H15B2.5000
C19···C16iv3.591 (5)H18···O1iv2.6800
C20···C16iv3.506 (5)H18···C23ii2.9400
C20···C17iv3.597 (5)H18···H23Aii2.5300
C20···C243.371 (6)H19···H13Aiv2.5000
C21···C19iv3.518 (5)H20···C242.9300
C22···C133.278 (4)H20···C233.0300
C22···Br13.523 (3)H20···H242.4400
C24···C203.371 (6)H20···Br2iv2.9100
C27···C14i3.449 (11)H22···Br12.6200
C1···H14B3.0200H22···C133.0800
C1···H27Bi2.9000H22···C142.7400
C2···H13B2.9400H22···H13A2.5200
C6···H27Bi3.0600H22···H14A2.2800
C8···H53.0300H22···H23B2.4900
C8···H12C2.5700H23A···H18iii2.5300
C12···H8A2.6800H23A···O1vii2.8900
C13···H23.0100H23A···C18iv3.0300
C13···H223.0800H23B···C272.5900
C14···H222.7400H23B···H222.4900
C15···H172.9800H23B···H27C2.1200
C17···H15B2.8900H24···C203.0900
C18···H23Aiv3.0300H24···H202.4400
C20···H11Ci3.0700H24···H26C2.5300
C20···H243.0900H24···Br2iv3.1100
C22···H14A2.7400H26A···H11Aviii2.2200
C22···H27C3.0400H26B···H27B2.3600
C22···H13A2.7200H26C···H242.5300
C23···H27C2.5200H27A···H12Bx2.4900
C23···H18iii2.9400H27A···H14Bi2.4500
C23···H203.0300H27B···H26B2.3600
C24···H202.9300H27B···N1i2.9300
C26···H11Aviii2.8800H27B···C1i2.9000
C27···H14Bi2.8800H27B···C6i3.0600
C27···H23B2.5900H27C···N42.8700
H1A···Br12.62 (6)H27C···C223.0400
H1A···H17iii2.4600H27C···C232.5200
H1B···Br2iii2.55 (5)H27C···H23B2.1200
H1A—O1—H1B104 (5)H8A—C8—H8B108.00
C1—N1—C7108.2 (2)N2—C8—H8A109.00
C7—N1—C13126.1 (2)C8—C9—H9117.00
C1—N1—C13125.7 (3)C10—C9—H9117.00
C6—N2—C7108.4 (3)C10—C11—H11B109.00
C7—N2—C8125.3 (2)C10—C11—H11C110.00
C6—N2—C8126.4 (2)C10—C11—H11A109.00
C15—N3—C16125.2 (3)H11A—C11—H11C110.00
C15—N3—C22127.2 (3)H11B—C11—H11C109.00
C16—N3—C22107.7 (2)H11A—C11—H11B109.00
C21—N4—C22108.5 (3)C10—C12—H12A110.00
C21—N4—C23125.8 (3)C10—C12—H12C109.00
C22—N4—C23125.5 (3)H12A—C12—H12B110.00
N1—C1—C6106.3 (2)C10—C12—H12B109.00
C2—C1—C6121.9 (3)H12B—C12—H12C109.00
N1—C1—C2131.8 (3)H12A—C12—H12C109.00
C1—C2—C3116.3 (3)N1—C13—H13B109.00
C2—C3—C4121.9 (3)C14—C13—H13A109.00
C3—C4—C5122.2 (3)N1—C13—H13A109.00
C4—C5—C6116.2 (3)H13A—C13—H13B108.00
N2—C6—C5131.8 (3)C14—C13—H13B109.00
C1—C6—C5121.5 (3)C13—C14—H14A109.00
N2—C6—C1106.7 (2)C15—C14—H14A109.00
N1—C7—N2110.5 (3)C15—C14—H14B109.00
N2—C8—C9111.9 (3)H14A—C14—H14B108.00
C8—C9—C10125.8 (4)C13—C14—H14B109.00
C9—C10—C11121.2 (4)N3—C15—H15B109.00
C11—C10—C12115.4 (5)C14—C15—H15A109.00
C9—C10—C12123.3 (5)N3—C15—H15A109.00
N1—C13—C14111.5 (3)H15A—C15—H15B108.00
C13—C14—C15114.0 (3)C14—C15—H15B109.00
N3—C15—C14113.3 (3)C18—C17—H17122.00
N3—C16—C17131.1 (3)C16—C17—H17122.00
C17—C16—C21121.7 (3)C17—C18—H18119.00
N3—C16—C21107.2 (3)C19—C18—H18119.00
C16—C17—C18115.6 (3)C20—C19—H19119.00
C17—C18—C19122.3 (3)C18—C19—H19119.00
C18—C19—C20122.6 (4)C19—C20—H20122.00
C19—C20—C21116.1 (3)C21—C20—H20122.00
N4—C21—C16106.1 (3)N4—C22—H22125.00
C16—C21—C20121.7 (3)N3—C22—H22125.00
N4—C21—C20132.2 (3)N4—C23—H23A108.00
N3—C22—N4110.5 (3)C24—C23—H23A108.00
N4—C23—C24115.4 (4)C24—C23—H23B109.00
C23—C24—C25124.2 (5)N4—C23—H23B108.00
C24—C25—C27119.1 (5)H23A—C23—H23B107.00
C26—C25—C27119.9 (6)C25—C24—H24118.00
C24—C25—C26120.5 (5)C23—C24—H24118.00
C3—C2—H2122.00C25—C26—H26A109.00
C1—C2—H2122.00C25—C26—H26B109.00
C2—C3—H3119.00H26A—C26—H26B109.00
C4—C3—H3119.00H26A—C26—H26C109.00
C5—C4—H4119.00C25—C26—H26C109.00
C3—C4—H4119.00H26B—C26—H26C109.00
C4—C5—H5122.00C25—C27—H27B109.00
C6—C5—H5122.00C25—C27—H27C109.00
N1—C7—H7125.00C25—C27—H27A110.00
N2—C7—H7125.00H27A—C27—H27C109.00
N2—C8—H8B109.00H27B—C27—H27C109.00
C9—C8—H8A109.00H27A—C27—H27B110.00
C9—C8—H8B109.00
C7—N1—C1—C2178.9 (4)C22—N4—C21—C160.1 (4)
C13—N1—C1—C20.1 (6)N1—C1—C6—C5178.9 (3)
C7—N1—C1—C60.9 (4)C2—C1—C6—N2179.0 (3)
C13—N1—C1—C6179.7 (3)N1—C1—C2—C3179.6 (4)
C1—N1—C7—N20.7 (4)C6—C1—C2—C30.2 (5)
C13—N1—C7—N2179.5 (3)C2—C1—C6—C51.0 (5)
C1—N1—C13—C1484.0 (4)N1—C1—C6—N20.8 (4)
C7—N1—C13—C1497.4 (4)C1—C2—C3—C40.2 (5)
C6—N2—C8—C969.2 (4)C2—C3—C4—C51.0 (6)
C7—N2—C8—C9111.1 (4)C3—C4—C5—C61.7 (5)
C7—N2—C6—C5178.2 (4)C4—C5—C6—N2179.2 (3)
C8—N2—C6—C51.6 (6)C4—C5—C6—C11.7 (5)
C7—N2—C6—C10.4 (4)N2—C8—C9—C1093.3 (4)
C6—N2—C7—N10.2 (4)C8—C9—C10—C121.3 (8)
C8—N2—C7—N1180.0 (3)C8—C9—C10—C11178.4 (5)
C8—N2—C6—C1179.4 (3)N1—C13—C14—C15170.1 (2)
C22—N3—C16—C17178.3 (4)C13—C14—C15—N362.0 (3)
C16—N3—C22—N41.3 (3)N3—C16—C21—N40.9 (3)
C16—N3—C15—C14154.7 (3)N3—C16—C17—C18179.7 (3)
C22—N3—C15—C1425.3 (4)C21—C16—C17—C180.7 (5)
C15—N3—C16—C21178.7 (3)C17—C16—C21—C201.7 (5)
C22—N3—C16—C211.4 (3)N3—C16—C21—C20178.6 (3)
C15—N3—C22—N4178.7 (3)C17—C16—C21—N4178.8 (3)
C15—N3—C16—C171.7 (5)C16—C17—C18—C190.3 (6)
C23—N4—C21—C204.5 (6)C17—C18—C19—C200.3 (6)
C21—N4—C23—C2458.5 (6)C18—C19—C20—C210.6 (5)
C22—N4—C23—C24127.6 (4)C19—C20—C21—N4179.1 (3)
C23—N4—C22—N3174.1 (3)C19—C20—C21—C161.5 (5)
C23—N4—C21—C16174.9 (3)N4—C23—C24—C2593.3 (6)
C22—N4—C21—C20179.4 (3)C23—C24—C25—C26179.9 (6)
C21—N4—C22—N30.8 (4)C23—C24—C25—C278.5 (9)
Symmetry codes: (i) x+1, y+1, z+1; (ii) x+1, y, z; (iii) x1, y, z; (iv) x+2, y+2, z+1; (v) x+1, y+1, z; (vi) x+2, y+1, z; (vii) x+1, y+2, z+1; (viii) x+1, y+1, z+1; (ix) x1, y1, z1; (x) x, y+1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1A···Br10.79 (6)2.62 (6)3.313 (4)146 (5)
O1—H1B···Br2iii0.82 (5)2.55 (5)3.360 (3)169 (5)
C7—H7···Br10.932.803.586 (3)142
C8—H8B···Br2v0.972.893.819 (3)160
C13—H13B···Br20.972.913.832 (3)159
C20—H20···Br2iv0.932.913.812 (3)163
C22—H22···Br10.932.623.523 (3)164
Symmetry codes: (iii) x1, y, z; (iv) x+2, y+2, z+1; (v) x+1, y+1, z.
 

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