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The title compound, C
22H
20N
2+·Br
−·H
2O, was synthesized from 1-benzylbenzimidazole and 2-bromoethylbenzene in dimethylformamide. The dihedral angle between the two phenyl rings is 70.6 (1)°. These phenyl rings make dihedral angles of 52.99 (9) and 83.03 (8)° with the benzimidazole ring system. The crystal structure is stabilized by intermolecular C—H
Br and O—H
Br hydrogen-bond interactions.
Supporting information
CCDC reference: 282308
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.003 Å
- R factor = 0.037
- wR factor = 0.100
- Data-to-parameter ratio = 16.5
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 ....... 0.66 mm
PLAT320_ALERT_2_C Check Hybridisation of C7 in Main Residue . ?
0 ALERT level A = In general: serious problem
0 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
1 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
0 ALERT type 4 Improvement, methodology, query or suggestion
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).
1-Benzyl-3-(2-phenethyl)benzimidazolium bromide monohydrate
top
Crystal data top
C22H20N2+·Br−·H2O | Z = 2 |
Mr = 410.32 | F(000) = 422 |
Triclinic, P1 | Dx = 1.422 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.2334 (9) Å | Cell parameters from 10373 reflections |
b = 9.3684 (10) Å | θ = 2.2–26.8° |
c = 11.3028 (12) Å | µ = 2.16 mm−1 |
α = 99.895 (8)° | T = 100 K |
β = 90.607 (8)° | Prism, colourless |
γ = 95.637 (8)° | 0.66 × 0.47 × 0.26 mm |
V = 958.14 (17) Å3 | |
Data collection top
Stoe IPDS-II diffractometer | 4023 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 3811 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.053 |
Detector resolution: 6.67 pixels mm-1 | θmax = 26.7°, θmin = 2.2° |
ω scans | h = −11→11 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −11→11 |
Tmin = 0.330, Tmax = 0.604 | l = −13→14 |
10373 measured reflections | |
Refinement top
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.100 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0662P)2 + 0.4181P] where P = (Fo2 + 2Fc2)/3 |
4023 reflections | (Δ/σ)max = 0.001 |
244 parameters | Δρmax = 1.45 e Å−3 |
0 restraints | Δρmin = −1.06 e Å−3 |
Special details top
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 | x | y | z | Uiso*/Ueq | |
N1 | 0.32580 (19) | 0.5492 (2) | 0.84749 (15) | 0.0169 (5) | |
N2 | 0.49570 (19) | 0.73024 (19) | 0.85838 (15) | 0.0162 (5) | |
C1 | 0.4580 (2) | 0.4893 (2) | 0.84798 (17) | 0.0167 (5) | |
C2 | 0.4898 (2) | 0.3469 (2) | 0.84448 (18) | 0.0197 (6) | |
C3 | 0.6362 (3) | 0.3269 (2) | 0.85125 (19) | 0.0218 (6) | |
C4 | 0.7453 (2) | 0.4444 (3) | 0.86176 (19) | 0.0214 (6) | |
C5 | 0.7138 (2) | 0.5856 (3) | 0.86393 (18) | 0.0189 (6) | |
C6 | 0.5664 (2) | 0.6057 (2) | 0.85612 (17) | 0.0161 (5) | |
C7 | 0.3524 (2) | 0.6923 (2) | 0.85220 (17) | 0.0173 (5) | |
C8 | 0.5652 (2) | 0.8795 (2) | 0.86259 (19) | 0.0186 (6) | |
C9 | 0.6364 (2) | 0.8973 (2) | 0.74607 (19) | 0.0168 (5) | |
C10 | 0.7840 (2) | 0.9455 (2) | 0.7454 (2) | 0.0220 (6) | |
C11 | 0.8481 (3) | 0.9662 (3) | 0.6382 (2) | 0.0283 (7) | |
C12 | 0.7675 (3) | 0.9368 (2) | 0.5321 (2) | 0.0271 (7) | |
C13 | 0.6196 (3) | 0.8881 (2) | 0.5320 (2) | 0.0235 (6) | |
C14 | 0.5544 (2) | 0.8696 (2) | 0.6392 (2) | 0.0200 (6) | |
C15 | 0.1798 (2) | 0.4689 (2) | 0.83453 (19) | 0.0198 (6) | |
C16 | 0.1471 (2) | 0.3936 (2) | 0.70472 (19) | 0.0212 (6) | |
C17 | 0.1739 (2) | 0.4971 (2) | 0.61673 (19) | 0.0184 (5) | |
C18 | 0.2836 (2) | 0.4774 (2) | 0.5335 (2) | 0.0213 (6) | |
C19 | 0.3105 (2) | 0.5724 (3) | 0.4531 (2) | 0.0227 (6) | |
C20 | 0.2297 (3) | 0.6889 (2) | 0.45547 (19) | 0.0218 (6) | |
C21 | 0.1212 (3) | 0.7106 (2) | 0.5389 (2) | 0.0234 (6) | |
C22 | 0.0927 (2) | 0.6148 (2) | 0.6185 (2) | 0.0215 (6) | |
O1 | −0.0329 (2) | 0.2233 (2) | 1.0233 (2) | 0.0351 (6) | |
Br1 | 0.19898 (2) | 0.03845 (2) | 0.84225 (2) | 0.0221 (1) | |
H2 | 0.41720 | 0.26960 | 0.83800 | 0.0240* | |
H3 | 0.66290 | 0.23330 | 0.84880 | 0.0260* | |
H4 | 0.84210 | 0.42620 | 0.86750 | 0.0260* | |
H5 | 0.78640 | 0.66290 | 0.87020 | 0.0230* | |
H8A | 0.63790 | 0.90200 | 0.92750 | 0.0220* | |
H8B | 0.49250 | 0.94770 | 0.87910 | 0.0220* | |
H10 | 0.83940 | 0.96390 | 0.81660 | 0.0260* | |
H11 | 0.94620 | 1.00010 | 0.63800 | 0.0340* | |
H12 | 0.81160 | 0.94940 | 0.46050 | 0.0330* | |
H13 | 0.56500 | 0.86810 | 0.46040 | 0.0280* | |
H14 | 0.45560 | 0.83860 | 0.63950 | 0.0240* | |
H15A | 0.10760 | 0.53580 | 0.85900 | 0.0240* | |
H15B | 0.17350 | 0.39660 | 0.88670 | 0.0240* | |
H16A | 0.20780 | 0.31440 | 0.68530 | 0.0260* | |
H16B | 0.04620 | 0.35210 | 0.69680 | 0.0260* | |
H18 | 0.33940 | 0.39970 | 0.53200 | 0.0260* | |
H19 | 0.38320 | 0.55750 | 0.39740 | 0.0270* | |
H20 | 0.24780 | 0.75270 | 0.40150 | 0.0260* | |
H21 | 0.06730 | 0.78980 | 0.54130 | 0.0280* | |
H22 | 0.01890 | 0.62940 | 0.67330 | 0.0260* | |
H1W | 0.019 (4) | 0.180 (4) | 0.971 (4) | 0.043 (10)* | |
H2W | −0.059 (5) | 0.164 (5) | 1.059 (4) | 0.053 (12)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0128 (8) | 0.0241 (9) | 0.0134 (8) | 0.0001 (7) | 0.0007 (6) | 0.0032 (6) |
N2 | 0.0142 (8) | 0.0206 (9) | 0.0135 (7) | 0.0005 (6) | 0.0009 (6) | 0.0027 (6) |
C1 | 0.0150 (9) | 0.0244 (10) | 0.0108 (8) | 0.0016 (8) | 0.0012 (7) | 0.0038 (7) |
C2 | 0.0220 (10) | 0.0220 (10) | 0.0149 (9) | 0.0010 (8) | 0.0025 (8) | 0.0035 (8) |
C3 | 0.0248 (11) | 0.0240 (10) | 0.0178 (10) | 0.0071 (9) | 0.0036 (8) | 0.0043 (8) |
C4 | 0.0164 (10) | 0.0321 (12) | 0.0170 (9) | 0.0067 (8) | 0.0031 (8) | 0.0051 (8) |
C5 | 0.0154 (10) | 0.0271 (11) | 0.0136 (9) | 0.0009 (8) | 0.0011 (7) | 0.0029 (8) |
C6 | 0.0158 (9) | 0.0219 (10) | 0.0105 (8) | 0.0021 (8) | 0.0020 (7) | 0.0023 (7) |
C7 | 0.0162 (9) | 0.0234 (10) | 0.0125 (9) | 0.0020 (8) | 0.0006 (7) | 0.0033 (8) |
C8 | 0.0174 (10) | 0.0185 (10) | 0.0188 (10) | −0.0007 (8) | −0.0006 (8) | 0.0016 (8) |
C9 | 0.0154 (9) | 0.0153 (9) | 0.0202 (10) | 0.0021 (7) | 0.0027 (7) | 0.0038 (7) |
C10 | 0.0152 (10) | 0.0200 (10) | 0.0301 (11) | 0.0014 (8) | 0.0002 (8) | 0.0026 (9) |
C11 | 0.0178 (11) | 0.0236 (11) | 0.0423 (14) | 0.0005 (8) | 0.0121 (10) | 0.0029 (10) |
C12 | 0.0330 (13) | 0.0203 (10) | 0.0294 (12) | 0.0050 (9) | 0.0167 (10) | 0.0057 (9) |
C13 | 0.0297 (12) | 0.0237 (10) | 0.0190 (10) | 0.0084 (9) | 0.0044 (9) | 0.0060 (8) |
C14 | 0.0152 (9) | 0.0243 (10) | 0.0207 (10) | 0.0029 (8) | 0.0015 (8) | 0.0043 (8) |
C15 | 0.0131 (9) | 0.0264 (11) | 0.0188 (10) | −0.0040 (8) | 0.0004 (7) | 0.0044 (8) |
C16 | 0.0185 (10) | 0.0241 (10) | 0.0200 (10) | −0.0012 (8) | −0.0030 (8) | 0.0028 (8) |
C17 | 0.0157 (9) | 0.0219 (10) | 0.0160 (9) | 0.0007 (8) | −0.0043 (7) | 0.0000 (8) |
C18 | 0.0205 (10) | 0.0234 (10) | 0.0195 (10) | 0.0059 (8) | −0.0012 (8) | 0.0006 (8) |
C19 | 0.0208 (10) | 0.0281 (11) | 0.0183 (10) | 0.0039 (9) | 0.0022 (8) | 0.0004 (8) |
C20 | 0.0242 (11) | 0.0236 (10) | 0.0171 (9) | 0.0013 (8) | −0.0026 (8) | 0.0034 (8) |
C21 | 0.0216 (11) | 0.0235 (10) | 0.0254 (11) | 0.0079 (8) | −0.0018 (8) | 0.0018 (9) |
C22 | 0.0172 (10) | 0.0266 (11) | 0.0200 (10) | 0.0055 (8) | 0.0014 (8) | 0.0003 (8) |
O1 | 0.0303 (10) | 0.0256 (9) | 0.0496 (12) | 0.0036 (8) | 0.0149 (9) | 0.0057 (9) |
Br1 | 0.0159 (1) | 0.0250 (1) | 0.0253 (1) | 0.0011 (1) | 0.0010 (1) | 0.0048 (1) |
Geometric parameters (Å, º) top
O1—H1W | 0.84 (4) | C18—C19 | 1.385 (3) |
O1—H2W | 0.76 (5) | C19—C20 | 1.378 (3) |
N1—C1 | 1.393 (3) | C20—C21 | 1.389 (4) |
N1—C15 | 1.471 (3) | C21—C22 | 1.386 (3) |
N1—C7 | 1.331 (3) | C2—H2 | 0.9300 |
N2—C7 | 1.334 (3) | C3—H3 | 0.9300 |
N2—C8 | 1.473 (3) | C4—H4 | 0.9300 |
N2—C6 | 1.389 (3) | C5—H5 | 0.9300 |
C1—C2 | 1.388 (3) | C8—H8A | 0.9700 |
C1—C6 | 1.396 (3) | C8—H8B | 0.9700 |
C2—C3 | 1.386 (3) | C10—H10 | 0.9300 |
C3—C4 | 1.406 (3) | C11—H11 | 0.9300 |
C4—C5 | 1.378 (4) | C12—H12 | 0.9300 |
C5—C6 | 1.396 (3) | C13—H13 | 0.9300 |
C8—C9 | 1.506 (3) | C14—H14 | 0.9300 |
C9—C10 | 1.394 (3) | C15—H15B | 0.9700 |
C9—C14 | 1.391 (3) | C15—H15A | 0.9700 |
C10—C11 | 1.389 (3) | C16—H16B | 0.9700 |
C11—C12 | 1.377 (3) | C16—H16A | 0.9700 |
C12—C13 | 1.397 (4) | C18—H18 | 0.9300 |
C13—C14 | 1.388 (3) | C19—H19 | 0.9300 |
C15—C16 | 1.528 (3) | C20—H20 | 0.9300 |
C16—C17 | 1.510 (3) | C21—H21 | 0.9300 |
C17—C18 | 1.394 (3) | C22—H22 | 0.9300 |
C17—C22 | 1.391 (3) | | |
| | | |
Br1···C2 | 3.7431 (19) | C5···H15Biv | 2.9700 |
Br1···C7i | 3.6824 (19) | C6···H19vi | 3.0700 |
Br1···O1 | 3.373 (2) | C7···H14 | 3.0800 |
Br1···O1ii | 3.356 (2) | C8···H5 | 3.0300 |
Br1···H1W | 2.54 (4) | C10···H3vii | 3.0700 |
Br1···H11iii | 3.2200 | C11···H20viii | 2.9600 |
Br1···H2 | 2.8200 | C11···H21x | 2.8500 |
Br1···H8Bi | 2.9700 | C12···H20viii | 2.8900 |
Br1···H2Wii | 2.61 (5) | C12···H21viii | 3.0900 |
Br1···H8Aiv | 2.9300 | C13···H13viii | 2.9700 |
O1···C5iv | 3.408 (3) | C13···H18vi | 2.7300 |
O1···C7v | 3.387 (3) | C15···H22 | 3.0200 |
O1···Br1 | 3.373 (2) | C15···H2 | 3.0200 |
O1···Br1ii | 3.356 (2) | C20···H16Bix | 3.0100 |
O1···H5iv | 2.6100 | C20···H14 | 3.0000 |
O1···H15Av | 2.5800 | C21···H16Bix | 3.0000 |
N1···C4iv | 3.350 (3) | C22···H15A | 2.9400 |
N1···N2 | 2.180 (3) | H1W···Br1 | 2.54 (4) |
N1···C3iv | 3.406 (3) | H2···C15 | 3.0200 |
N2···N1 | 2.180 (3) | H2···Br1 | 2.8200 |
N2···H14 | 2.8600 | H2W···Br1ii | 2.61 (5) |
C1···C1iv | 3.483 (3) | H3···C10i | 3.0700 |
C1···C2iv | 3.558 (3) | H4···H15Ax | 2.5700 |
C2···C6iv | 3.389 (3) | H5···C8 | 3.0300 |
C2···Br1 | 3.7431 (19) | H5···O1iv | 2.6100 |
C2···C1iv | 3.558 (3) | H8A···Br1iv | 2.9300 |
C3···N1iv | 3.406 (3) | H8A···C5 | 3.0800 |
C3···C7iv | 3.389 (3) | H8A···H10 | 2.3400 |
C4···N1iv | 3.350 (3) | H8B···Br1vii | 2.9700 |
C4···C15iv | 3.436 (3) | H10···H8A | 2.3400 |
C4···C19vi | 3.565 (3) | H11···Br1xi | 3.2200 |
C5···C9 | 3.541 (3) | H11···H12xii | 2.5500 |
C5···O1iv | 3.408 (3) | H11···H21x | 2.4600 |
C6···C2iv | 3.389 (3) | H12···H21viii | 2.5900 |
C7···Br1vii | 3.6824 (19) | H12···H11xii | 2.5500 |
C7···O1v | 3.387 (3) | H13···C13viii | 2.9700 |
C7···C17 | 3.284 (3) | H14···C20 | 3.0000 |
C7···C14 | 3.591 (3) | H14···N2 | 2.8600 |
C7···C3iv | 3.389 (3) | H14···C7 | 3.0800 |
C7···C22 | 3.481 (3) | H15A···H22 | 2.5700 |
C9···C5 | 3.541 (3) | H15A···O1v | 2.5800 |
C12···C20viii | 3.483 (3) | H15A···C22 | 2.9400 |
C12···C21viii | 3.588 (3) | H15A···H4xiii | 2.5700 |
C13···C18vi | 3.580 (3) | H15B···C5iv | 2.9700 |
C13···C13viii | 3.346 (3) | H15B···C2 | 3.0300 |
C14···C7 | 3.591 (3) | H15B···C4iv | 3.0200 |
C15···C4iv | 3.436 (3) | H16A···H18 | 2.3300 |
C17···C22ix | 3.553 (3) | H16A···C1 | 3.0900 |
C17···C21ix | 3.462 (3) | H16B···C20ix | 3.0100 |
C17···C7 | 3.284 (3) | H16B···C21ix | 3.0000 |
C18···C13vi | 3.580 (3) | H18···C13vi | 2.7300 |
C19···C4vi | 3.565 (3) | H18···H16A | 2.3300 |
C20···C12viii | 3.483 (3) | H19···C6vi | 3.0700 |
C21···C12viii | 3.588 (3) | H20···C3vi | 3.0600 |
C21···C17ix | 3.462 (3) | H20···C11viii | 2.9600 |
C22···C17ix | 3.553 (3) | H20···C12viii | 2.8900 |
C22···C22ix | 3.454 (3) | H21···C12viii | 3.0900 |
C22···C7 | 3.481 (3) | H21···C11xiii | 2.8500 |
C1···H16A | 3.0900 | H21···H11xiii | 2.4600 |
C2···H15B | 3.0300 | H21···H12viii | 2.5900 |
C3···H20vi | 3.0600 | H22···C15 | 3.0200 |
C4···H15Biv | 3.0200 | H22···H15A | 2.5700 |
C5···H8A | 3.0800 | | |
| | | |
H1W—O1—H2W | 103 (4) | C2—C3—H3 | 119.00 |
C1—N1—C7 | 108.76 (17) | C3—C4—H4 | 119.00 |
C7—N1—C15 | 124.55 (17) | C5—C4—H4 | 119.00 |
C1—N1—C15 | 126.54 (17) | C6—C5—H5 | 122.00 |
C6—N2—C8 | 126.43 (16) | C4—C5—H5 | 122.00 |
C7—N2—C8 | 124.91 (17) | N2—C8—H8A | 109.00 |
C6—N2—C7 | 108.63 (17) | C9—C8—H8A | 109.00 |
N1—C1—C6 | 106.16 (17) | C9—C8—H8B | 109.00 |
C2—C1—C6 | 122.33 (17) | N2—C8—H8B | 109.00 |
N1—C1—C2 | 131.49 (18) | H8A—C8—H8B | 108.00 |
C1—C2—C3 | 115.99 (17) | C11—C10—H10 | 120.00 |
C2—C3—C4 | 121.71 (19) | C9—C10—H10 | 120.00 |
C3—C4—C5 | 122.30 (19) | C12—C11—H11 | 120.00 |
C4—C5—C6 | 116.0 (2) | C10—C11—H11 | 120.00 |
N2—C6—C5 | 131.7 (2) | C11—C12—H12 | 120.00 |
C1—C6—C5 | 121.63 (19) | C13—C12—H12 | 120.00 |
N2—C6—C1 | 106.60 (16) | C12—C13—H13 | 120.00 |
N1—C7—N2 | 109.83 (17) | C14—C13—H13 | 120.00 |
N2—C8—C9 | 111.57 (16) | C13—C14—H14 | 120.00 |
C8—C9—C14 | 120.18 (17) | C9—C14—H14 | 120.00 |
C10—C9—C14 | 119.72 (19) | N1—C15—H15A | 109.00 |
C8—C9—C10 | 120.07 (18) | N1—C15—H15B | 109.00 |
C9—C10—C11 | 119.8 (2) | C16—C15—H15B | 109.00 |
C10—C11—C12 | 120.5 (2) | H15A—C15—H15B | 108.00 |
C11—C12—C13 | 120.0 (2) | C16—C15—H15A | 109.00 |
C12—C13—C14 | 119.8 (2) | C15—C16—H16B | 109.00 |
C9—C14—C13 | 120.19 (19) | C17—C16—H16A | 109.00 |
N1—C15—C16 | 111.07 (16) | C17—C16—H16B | 109.00 |
C15—C16—C17 | 112.18 (16) | H16A—C16—H16B | 108.00 |
C16—C17—C18 | 120.05 (17) | C15—C16—H16A | 109.00 |
C16—C17—C22 | 121.13 (18) | C19—C18—H18 | 120.00 |
C18—C17—C22 | 118.81 (18) | C17—C18—H18 | 120.00 |
C17—C18—C19 | 120.69 (18) | C18—C19—H19 | 120.00 |
C18—C19—C20 | 120.17 (19) | C20—C19—H19 | 120.00 |
C19—C20—C21 | 119.66 (19) | C21—C20—H20 | 120.00 |
C20—C21—C22 | 120.4 (2) | C19—C20—H20 | 120.00 |
C17—C22—C21 | 120.3 (2) | C20—C21—H21 | 120.00 |
C1—C2—H2 | 122.00 | C22—C21—H21 | 120.00 |
C3—C2—H2 | 122.00 | C17—C22—H22 | 120.00 |
C4—C3—H3 | 119.00 | C21—C22—H22 | 120.00 |
| | | |
C7—N1—C1—C2 | 179.9 (2) | C3—C4—C5—C6 | 0.6 (3) |
C15—N1—C1—C2 | −4.5 (3) | C4—C5—C6—N2 | 178.3 (2) |
C7—N1—C1—C6 | 1.4 (2) | C4—C5—C6—C1 | 0.7 (3) |
C15—N1—C1—C6 | 176.97 (18) | N2—C8—C9—C10 | −123.40 (19) |
C1—N1—C15—C16 | −74.7 (2) | N2—C8—C9—C14 | 58.4 (2) |
C7—N1—C15—C16 | 100.3 (2) | C14—C9—C10—C11 | 0.3 (3) |
C15—N1—C7—N2 | −177.05 (17) | C8—C9—C14—C13 | 179.04 (18) |
C1—N1—C7—N2 | −1.3 (2) | C10—C9—C14—C13 | 0.8 (3) |
C8—N2—C7—N1 | 178.83 (17) | C8—C9—C10—C11 | −177.9 (2) |
C6—N2—C8—C9 | 70.0 (2) | C9—C10—C11—C12 | −1.2 (4) |
C7—N2—C6—C5 | −177.8 (2) | C10—C11—C12—C13 | 1.1 (4) |
C8—N2—C6—C5 | 4.2 (3) | C11—C12—C13—C14 | 0.0 (3) |
C7—N2—C8—C9 | −107.7 (2) | C12—C13—C14—C9 | −1.0 (3) |
C6—N2—C7—N1 | 0.8 (2) | N1—C15—C16—C17 | −51.7 (2) |
C7—N2—C6—C1 | 0.1 (2) | C15—C16—C17—C18 | 114.9 (2) |
C8—N2—C6—C1 | −177.93 (18) | C15—C16—C17—C22 | −63.7 (2) |
N1—C1—C6—N2 | −0.9 (2) | C16—C17—C22—C21 | 178.46 (19) |
N1—C1—C2—C3 | −177.5 (2) | C18—C17—C22—C21 | −0.2 (3) |
C6—C1—C2—C3 | 0.9 (3) | C22—C17—C18—C19 | −0.6 (3) |
C2—C1—C6—N2 | −179.57 (18) | C16—C17—C18—C19 | −179.29 (19) |
N1—C1—C6—C5 | 177.25 (18) | C17—C18—C19—C20 | 0.7 (3) |
C2—C1—C6—C5 | −1.5 (3) | C18—C19—C20—C21 | 0.0 (3) |
C1—C2—C3—C4 | 0.4 (3) | C19—C20—C21—C22 | −0.8 (4) |
C2—C3—C4—C5 | −1.1 (3) | C20—C21—C22—C17 | 0.9 (3) |
Symmetry codes: (i) x, y−1, z; (ii) −x, −y, −z+2; (iii) x−1, y−1, z; (iv) −x+1, −y+1, −z+2; (v) −x, −y+1, −z+2; (vi) −x+1, −y+1, −z+1; (vii) x, y+1, z; (viii) −x+1, −y+2, −z+1; (ix) −x, −y+1, −z+1; (x) x+1, y, z; (xi) x+1, y+1, z; (xii) −x+2, −y+2, −z+1; (xiii) x−1, y, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1W···Br1 | 0.84 (4) | 2.54 (4) | 3.373 (2) | 170 (4) |
O1—H2W···Br1ii | 0.76 (5) | 2.61 (5) | 3.356 (2) | 168 (5) |
C2—H2···Br1 | 0.93 | 2.82 | 3.7431 (19) | 175 |
C15—H15A···O1v | 0.97 | 2.58 | 3.458 (3) | 151 |
Symmetry codes: (ii) −x, −y, −z+2; (v) −x, −y+1, −z+2. |
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