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The title compound, C
21H
27N
32+·2Cl
−·H
2O, was synthesized from 1-benzylbenzimidazole and 2-chloroethylpiperidine hydrochloride in dimethylformamide. In the cation, the benzimidazole ring is connected to the piperidine ring by an ethylene group. The crystal structure is stabilized by O—H
Cl, N—H
Cl, C—H
O and C—H
Cl hydrogen-bonding interactions.
Supporting information
CCDC reference: 277797
Key indicators
- Single-crystal X-ray study
- T = 100 K
- Mean (C-C) = 0.002 Å
- R factor = 0.031
- wR factor = 0.078
- Data-to-parameter ratio = 17.4
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 ....... 0.78 mm
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.37
PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.55 Ratio
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
4 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
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-(1-piperidinio)ethyl]benzimidazolium dichloride monohydrate
top
Crystal data top
C21H27N32+·2Cl−·H2O | F(000) = 872 |
Mr = 410.37 | Dx = 1.307 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 32468 reflections |
a = 17.1422 (12) Å | θ = 1.9–27.2° |
b = 6.9643 (3) Å | µ = 0.33 mm−1 |
c = 18.2627 (13) Å | T = 100 K |
β = 106.961 (5)° | Plate, colourless |
V = 2085.4 (2) Å3 | 0.78 × 0.49 × 0.18 mm |
Z = 4 | |
Data collection top
STOE IPDS-II diffractometer | 4535 independent reflections |
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus | 3875 reflections with I > 2σ(I) |
Plane graphite monochromator | Rint = 0.032 |
Detector resolution: 6.67 pixels mm-1 | θmax = 27.0°, θmin = 1.9° |
ω scans | h = −21→21 |
Absorption correction: integration (X-RED32; Stoe & Cie, 2002) | k = −8→8 |
Tmin = 0.784, Tmax = 0.943 | l = −23→22 |
17638 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)] = 0.031 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.078 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0383P)2 + 0.7441P] where P = (Fo2 + 2Fc2)/3 |
4535 reflections | (Δ/σ)max = 0.001 |
260 parameters | Δρmax = 0.43 e Å−3 |
0 restraints | Δρmin = −0.18 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 | 0.60526 (6) | 0.60317 (15) | 0.72070 (6) | 0.0180 (3) | |
N2 | 0.66715 (6) | 0.56138 (16) | 0.63281 (6) | 0.0178 (3) | |
N3 | 0.75431 (7) | 0.67803 (17) | 0.47262 (6) | 0.0210 (3) | |
C1 | 0.68830 (7) | 0.58849 (17) | 0.75901 (7) | 0.0175 (3) | |
C2 | 0.73043 (8) | 0.59974 (18) | 0.83650 (7) | 0.0189 (3) | |
C3 | 0.81446 (8) | 0.58467 (18) | 0.85470 (7) | 0.0205 (3) | |
C4 | 0.85466 (8) | 0.56040 (18) | 0.79863 (8) | 0.0208 (4) | |
C5 | 0.81249 (8) | 0.55002 (18) | 0.72131 (7) | 0.0196 (3) | |
C6 | 0.72793 (7) | 0.56407 (18) | 0.70307 (7) | 0.0176 (3) | |
C7 | 0.53983 (8) | 0.63691 (19) | 0.75667 (8) | 0.0203 (3) | |
C8 | 0.51394 (7) | 0.45483 (19) | 0.78796 (7) | 0.0192 (3) | |
C9 | 0.51512 (9) | 0.4445 (2) | 0.86433 (8) | 0.0267 (4) | |
C10 | 0.48832 (10) | 0.2787 (3) | 0.89199 (9) | 0.0349 (5) | |
C11 | 0.46069 (9) | 0.1245 (2) | 0.84372 (10) | 0.0329 (5) | |
C12 | 0.45889 (8) | 0.1345 (2) | 0.76784 (9) | 0.0286 (4) | |
C13 | 0.48578 (8) | 0.2990 (2) | 0.74012 (8) | 0.0238 (4) | |
C14 | 0.59529 (8) | 0.58574 (18) | 0.64612 (7) | 0.0188 (3) | |
C15 | 0.67969 (8) | 0.53321 (19) | 0.55762 (7) | 0.0196 (3) | |
C16 | 0.71756 (8) | 0.71403 (19) | 0.53550 (7) | 0.0198 (3) | |
C17 | 0.69267 (9) | 0.6072 (2) | 0.40136 (8) | 0.0279 (4) | |
C18 | 0.73319 (11) | 0.5676 (3) | 0.33926 (9) | 0.0366 (5) | |
C19 | 0.77631 (12) | 0.7436 (3) | 0.32246 (10) | 0.0446 (6) | |
C20 | 0.83604 (11) | 0.8219 (3) | 0.39494 (11) | 0.0431 (6) | |
C21 | 0.79498 (10) | 0.8575 (2) | 0.45719 (10) | 0.0315 (5) | |
O1 | 0.49086 (7) | 0.26239 (16) | 0.54011 (6) | 0.0284 (3) | |
Cl1 | 0.41634 (2) | 0.86809 (5) | 0.57854 (2) | 0.0257 (1) | |
Cl2 | 0.86696 (2) | 0.34916 (5) | 0.53733 (2) | 0.0275 (1) | |
H2 | 0.70380 | 0.61640 | 0.87370 | 0.0230* | |
H3 | 0.84520 | 0.59090 | 0.90580 | 0.0250* | |
H3A | 0.7923 (10) | 0.583 (2) | 0.4890 (9) | 0.026 (4)* | |
H4 | 0.91120 | 0.55100 | 0.81370 | 0.0250* | |
H5 | 0.83910 | 0.53460 | 0.68400 | 0.0240* | |
H7A | 0.49310 | 0.69230 | 0.71910 | 0.0240* | |
H7B | 0.55870 | 0.72880 | 0.79800 | 0.0240* | |
H9 | 0.53380 | 0.54820 | 0.89680 | 0.0320* | |
H10 | 0.48900 | 0.27160 | 0.94300 | 0.0420* | |
H11 | 0.44320 | 0.01350 | 0.86250 | 0.0400* | |
H12 | 0.43970 | 0.03110 | 0.73540 | 0.0340* | |
H13 | 0.48500 | 0.30520 | 0.68900 | 0.0290* | |
H15A | 0.62790 | 0.50680 | 0.51980 | 0.0230* | |
H15B | 0.71550 | 0.42440 | 0.55930 | 0.0230* | |
H16A | 0.67590 | 0.81230 | 0.51960 | 0.0240* | |
H16B | 0.75930 | 0.76180 | 0.57990 | 0.0240* | |
H17A | 0.65020 | 0.70280 | 0.38350 | 0.0330* | |
H17B | 0.66750 | 0.49050 | 0.41270 | 0.0330* | |
H18A | 0.77220 | 0.46390 | 0.35550 | 0.0440* | |
H18B | 0.69230 | 0.52700 | 0.29300 | 0.0440* | |
H19A | 0.73640 | 0.84170 | 0.29980 | 0.0540* | |
H19B | 0.80540 | 0.71130 | 0.28590 | 0.0540* | |
H20A | 0.85910 | 0.94120 | 0.38330 | 0.0520* | |
H20B | 0.88030 | 0.73100 | 0.41350 | 0.0520* | |
H21A | 0.83540 | 0.89890 | 0.50370 | 0.0380* | |
H21B | 0.75480 | 0.95890 | 0.44110 | 0.0380* | |
H24 | 0.5453 (10) | 0.591 (2) | 0.6091 (9) | 0.023 (4)* | |
H22 | 0.4721 (13) | 0.160 (3) | 0.5524 (12) | 0.048 (6)* | |
H23 | 0.5183 (13) | 0.229 (3) | 0.5104 (12) | 0.044 (6)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
N1 | 0.0178 (5) | 0.0179 (5) | 0.0186 (5) | 0.0005 (4) | 0.0058 (4) | 0.0013 (4) |
N2 | 0.0176 (5) | 0.0189 (5) | 0.0165 (5) | −0.0002 (4) | 0.0042 (4) | −0.0005 (4) |
N3 | 0.0221 (5) | 0.0205 (5) | 0.0222 (5) | 0.0024 (4) | 0.0091 (4) | 0.0010 (4) |
C1 | 0.0179 (6) | 0.0144 (6) | 0.0198 (6) | −0.0005 (4) | 0.0048 (5) | 0.0008 (5) |
C2 | 0.0238 (6) | 0.0154 (6) | 0.0182 (6) | −0.0013 (5) | 0.0071 (5) | 0.0003 (5) |
C3 | 0.0240 (6) | 0.0154 (6) | 0.0190 (6) | −0.0016 (5) | 0.0015 (5) | 0.0002 (5) |
C4 | 0.0186 (6) | 0.0159 (6) | 0.0258 (7) | −0.0009 (5) | 0.0031 (5) | 0.0009 (5) |
C5 | 0.0201 (6) | 0.0172 (6) | 0.0225 (6) | 0.0012 (5) | 0.0076 (5) | 0.0000 (5) |
C6 | 0.0203 (6) | 0.0145 (6) | 0.0170 (6) | −0.0002 (5) | 0.0039 (5) | 0.0001 (4) |
C7 | 0.0184 (6) | 0.0210 (6) | 0.0234 (6) | 0.0016 (5) | 0.0089 (5) | −0.0001 (5) |
C8 | 0.0144 (5) | 0.0211 (6) | 0.0229 (6) | 0.0017 (5) | 0.0066 (5) | 0.0010 (5) |
C9 | 0.0267 (7) | 0.0305 (7) | 0.0241 (7) | −0.0058 (6) | 0.0095 (6) | −0.0023 (6) |
C10 | 0.0361 (8) | 0.0435 (9) | 0.0277 (7) | −0.0081 (7) | 0.0136 (6) | 0.0064 (7) |
C11 | 0.0273 (7) | 0.0288 (8) | 0.0439 (9) | −0.0042 (6) | 0.0123 (6) | 0.0095 (7) |
C12 | 0.0226 (7) | 0.0228 (7) | 0.0395 (8) | −0.0018 (5) | 0.0076 (6) | −0.0035 (6) |
C13 | 0.0222 (6) | 0.0249 (7) | 0.0241 (7) | 0.0012 (5) | 0.0063 (5) | −0.0017 (5) |
C14 | 0.0178 (6) | 0.0180 (6) | 0.0195 (6) | −0.0001 (5) | 0.0039 (5) | 0.0012 (5) |
C15 | 0.0222 (6) | 0.0201 (6) | 0.0167 (6) | −0.0004 (5) | 0.0062 (5) | −0.0019 (5) |
C16 | 0.0216 (6) | 0.0203 (6) | 0.0182 (6) | 0.0003 (5) | 0.0071 (5) | −0.0013 (5) |
C17 | 0.0300 (7) | 0.0353 (8) | 0.0180 (6) | 0.0018 (6) | 0.0066 (5) | −0.0020 (6) |
C18 | 0.0441 (9) | 0.0457 (9) | 0.0233 (7) | 0.0096 (7) | 0.0152 (7) | −0.0010 (7) |
C19 | 0.0551 (11) | 0.0507 (11) | 0.0389 (9) | 0.0161 (9) | 0.0306 (8) | 0.0128 (8) |
C20 | 0.0463 (10) | 0.0369 (9) | 0.0603 (11) | 0.0038 (7) | 0.0378 (9) | 0.0084 (8) |
C21 | 0.0345 (8) | 0.0222 (7) | 0.0448 (9) | −0.0006 (6) | 0.0227 (7) | 0.0038 (6) |
O1 | 0.0287 (5) | 0.0245 (5) | 0.0316 (6) | 0.0005 (4) | 0.0084 (5) | −0.0021 (4) |
Cl1 | 0.0263 (2) | 0.0256 (2) | 0.0248 (2) | 0.0013 (1) | 0.0068 (1) | 0.0020 (1) |
Cl2 | 0.0261 (2) | 0.0262 (2) | 0.0324 (2) | 0.0062 (1) | 0.0119 (1) | 0.0060 (1) |
Geometric parameters (Å, º) top
O1—H22 | 0.84 (2) | C19—C20 | 1.519 (3) |
O1—H23 | 0.85 (2) | C20—C21 | 1.522 (3) |
N1—C1 | 1.3947 (16) | C2—H2 | 0.9300 |
N1—C14 | 1.3279 (16) | C3—H3 | 0.9300 |
N1—C7 | 1.4747 (18) | C4—H4 | 0.9300 |
N2—C14 | 1.3342 (18) | C5—H5 | 0.9300 |
N2—C6 | 1.3973 (16) | C7—H7B | 0.9700 |
N2—C15 | 1.4637 (16) | C7—H7A | 0.9700 |
N3—C17 | 1.5004 (18) | C9—H9 | 0.9300 |
N3—C16 | 1.4834 (17) | C10—H10 | 0.9300 |
N3—C21 | 1.4974 (19) | C11—H11 | 0.9300 |
N3—H3A | 0.915 (16) | C12—H12 | 0.9300 |
C1—C2 | 1.3907 (17) | C13—H13 | 0.9300 |
C1—C6 | 1.3925 (18) | C14—H24 | 0.925 (17) |
C2—C3 | 1.385 (2) | C15—H15A | 0.9700 |
C3—C4 | 1.4013 (19) | C15—H15B | 0.9700 |
C4—C5 | 1.3879 (19) | C16—H16B | 0.9700 |
C5—C6 | 1.3928 (19) | C16—H16A | 0.9700 |
C7—C8 | 1.5098 (19) | C17—H17A | 0.9700 |
C8—C13 | 1.3885 (19) | C17—H17B | 0.9700 |
C8—C9 | 1.3908 (19) | C18—H18A | 0.9700 |
C9—C10 | 1.391 (2) | C18—H18B | 0.9700 |
C10—C11 | 1.382 (2) | C19—H19B | 0.9700 |
C11—C12 | 1.379 (2) | C19—H19A | 0.9700 |
C12—C13 | 1.385 (2) | C20—H20A | 0.9700 |
C15—C16 | 1.5243 (19) | C20—H20B | 0.9700 |
C17—C18 | 1.518 (2) | C21—H21B | 0.9700 |
C18—C19 | 1.508 (3) | C21—H21A | 0.9700 |
| | | |
Cl1···C14 | 3.5484 (14) | C15···H17B | 2.6100 |
Cl1···O1i | 3.1722 (12) | C17···H13i | 3.0700 |
Cl1···O1ii | 3.1919 (12) | C17···H15A | 2.7900 |
Cl2···N3 | 3.0066 (13) | C17···H15B | 3.0700 |
Cl2···C16 | 3.6010 (14) | C19···H18Bix | 3.0500 |
Cl2···C9iii | 3.6243 (15) | H2···C7 | 3.0000 |
Cl2···C15 | 3.5749 (15) | H2···H7B | 2.5900 |
Cl1···H21Biv | 3.0900 | H2···Cl2vii | 2.8100 |
Cl1···H23i | 2.33 (2) | H3···H23vii | 2.5800 |
Cl1···H3v | 3.0500 | H3···Cl1x | 3.0500 |
Cl1···H7A | 2.8000 | H3···H16Aiii | 2.4600 |
Cl1···H12ii | 3.0000 | H3A···H15B | 2.3600 |
Cl1···H15Ai | 3.1300 | H3A···H20B | 2.5400 |
Cl1···H24 | 2.864 (16) | H3A···H18A | 2.5000 |
Cl1···H17Bi | 2.9100 | H3A···Cl2 | 2.100 (15) |
Cl1···H22ii | 2.35 (2) | H4···H13vii | 2.5200 |
Cl1···H16Aiv | 3.0000 | H4···C12vii | 3.0700 |
Cl2···H5 | 3.1300 | H4···C13vii | 2.8400 |
Cl2···H15B | 2.7900 | H5···C15 | 3.0200 |
Cl2···H2iii | 2.8100 | H5···Cl2 | 3.1300 |
Cl2···H7Biii | 3.0200 | H5···H16B | 2.5400 |
Cl2···H3A | 2.100 (15) | H7A···H12ii | 2.5800 |
Cl2···H9iii | 2.7500 | H7A···Cl1 | 2.8000 |
O1···C14 | 3.1626 (17) | H7A···H24 | 2.5300 |
O1···Cl1i | 3.1722 (12) | H7B···H2 | 2.5900 |
O1···C15i | 3.2734 (18) | H7B···H9 | 2.3400 |
O1···Cl1vi | 3.1919 (12) | H7B···C2 | 2.9600 |
O1···H13 | 2.7700 | H7B···Cl2vii | 3.0200 |
O1···H24i | 2.805 (16) | H9···H7B | 2.3400 |
O1···H16Ai | 2.8000 | H9···Cl2vii | 2.7500 |
O1···H15Ai | 2.5700 | H11···H20Bxi | 2.3500 |
O1···H24 | 2.648 (15) | H12···Cl1vi | 3.0000 |
N1···N2 | 2.1864 (15) | H12···H7Avi | 2.5800 |
N1···C4vii | 3.2982 (17) | H13···H4iii | 2.5200 |
N2···C3iii | 3.3364 (17) | H13···C14 | 2.9800 |
N2···N1 | 2.1864 (15) | H13···N1 | 2.8600 |
N3···Cl2 | 3.0066 (13) | H13···O1 | 2.7700 |
N1···H13 | 2.8600 | H13···C17i | 3.0700 |
C1···C5vii | 3.2347 (17) | H13···H17Ai | 2.3100 |
C1···C4vii | 3.4640 (18) | H15A···C17 | 2.7900 |
C1···C6vii | 3.5960 (17) | H15A···H17B | 2.2500 |
C2···C16iii | 3.5013 (18) | H15A···O1i | 2.5700 |
C2···C6vii | 3.4336 (18) | H15A···H24 | 2.5200 |
C2···C5vii | 3.3221 (18) | H15A···Cl1i | 3.1300 |
C3···N2vii | 3.3364 (17) | H15B···C3iii | 2.9700 |
C3···C6vii | 3.5129 (18) | H15B···Cl2 | 2.7900 |
C3···C16iii | 3.4099 (18) | H15B···C17 | 3.0700 |
C3···C15vii | 3.4983 (18) | H15B···H3A | 2.3600 |
C4···C13vii | 3.446 (2) | H15B···C2iii | 2.9300 |
C4···C14iii | 3.4895 (18) | H15B···C5 | 3.0700 |
C4···C1iii | 3.4640 (18) | H16A···H17A | 2.5100 |
C4···N1iii | 3.2982 (17) | H16A···C3vii | 2.9500 |
C5···C16 | 3.4994 (18) | H16A···H3vii | 2.4600 |
C5···C2iii | 3.3221 (18) | H16A···H21B | 2.4600 |
C5···C1iii | 3.2347 (17) | H16A···Cl1iv | 3.0000 |
C6···C3iii | 3.5129 (18) | H16A···O1i | 2.8000 |
C6···C2iii | 3.4336 (18) | H16A···H22i | 2.5000 |
C6···C1iii | 3.5960 (17) | H16B···C5 | 2.8800 |
C9···Cl2vii | 3.6243 (15) | H16B···C6 | 2.8200 |
C13···C17i | 3.442 (2) | H16B···C2vii | 2.7800 |
C13···C14 | 3.513 (2) | H16B···H21A | 2.3700 |
C13···C4iii | 3.446 (2) | H16B···C3vii | 2.9900 |
C14···Cl1 | 3.5484 (14) | H16B···H5 | 2.5400 |
C14···O1 | 3.1626 (17) | H17A···H13i | 2.3100 |
C14···C4vii | 3.4895 (18) | H17A···C12i | 3.0700 |
C14···C13 | 3.513 (2) | H17A···C13i | 2.7300 |
C15···Cl2 | 3.5749 (15) | H17A···H21B | 2.5300 |
C15···C3iii | 3.4983 (18) | H17A···H16A | 2.5100 |
C15···O1i | 3.2734 (18) | H17B···C15 | 2.6100 |
C16···C5 | 3.4994 (18) | H17B···H15A | 2.2500 |
C16···C3vii | 3.4099 (18) | H17B···Cl1i | 2.9100 |
C16···C2vii | 3.5013 (18) | H18A···H3A | 2.5000 |
C16···Cl2 | 3.6010 (14) | H18B···C19xii | 3.0500 |
C17···C13i | 3.442 (2) | H20A···C9xiii | 2.9100 |
C2···H16Biii | 2.7800 | H20A···C10xiii | 2.9200 |
C2···H15Bvii | 2.9300 | H20B···H3A | 2.5400 |
C2···H7B | 2.9600 | H20B···H11xiv | 2.3500 |
C3···H16Biii | 2.9900 | H21A···C9vii | 2.9800 |
C3···H15Bvii | 2.9700 | H21A···H16B | 2.3700 |
C3···H16Aiii | 2.9500 | H21B···H17A | 2.5300 |
C5···H16B | 2.8800 | H21B···Cl1iv | 3.0900 |
C5···H15B | 3.0700 | H21B···H16A | 2.4600 |
C6···H16B | 2.8200 | H22···H16Ai | 2.5000 |
C7···H2 | 3.0000 | H22···Cl1vi | 2.35 (2) |
C9···H20Aviii | 2.9100 | H23···H24i | 2.48 (3) |
C9···H21Aiii | 2.9800 | H23···Cl1i | 2.33 (2) |
C10···H20Aviii | 2.9200 | H23···H3iii | 2.5800 |
C12···H4iii | 3.0700 | H24···H23i | 2.48 (3) |
C12···H17Ai | 3.0700 | H24···Cl1 | 2.864 (16) |
C13···H4iii | 2.8400 | H24···O1 | 2.648 (15) |
C13···H17Ai | 2.7300 | H24···H7A | 2.5300 |
C14···H13 | 2.9800 | H24···H15A | 2.5200 |
C15···H5 | 3.0200 | H24···O1i | 2.805 (16) |
| | | |
H22—O1—H23 | 105 (2) | N1—C7—H7A | 109.00 |
C1—N1—C7 | 125.86 (11) | H7A—C7—H7B | 108.00 |
C1—N1—C14 | 108.36 (11) | C8—C7—H7B | 109.00 |
C7—N1—C14 | 125.76 (11) | C8—C9—H9 | 120.00 |
C6—N2—C14 | 108.17 (10) | C10—C9—H9 | 120.00 |
C6—N2—C15 | 126.09 (11) | C11—C10—H10 | 120.00 |
C14—N2—C15 | 125.74 (11) | C9—C10—H10 | 120.00 |
C16—N3—C21 | 109.32 (11) | C10—C11—H11 | 120.00 |
C17—N3—C21 | 111.10 (11) | C12—C11—H11 | 120.00 |
C16—N3—C17 | 112.11 (11) | C13—C12—H12 | 120.00 |
C21—N3—H3A | 109.8 (10) | C11—C12—H12 | 120.00 |
C16—N3—H3A | 107.0 (10) | C8—C13—H13 | 120.00 |
C17—N3—H3A | 107.4 (10) | C12—C13—H13 | 120.00 |
N1—C1—C2 | 131.10 (12) | N2—C14—H24 | 125.4 (11) |
C2—C1—C6 | 122.26 (12) | N1—C14—H24 | 124.1 (11) |
N1—C1—C6 | 106.61 (10) | N2—C15—H15A | 110.00 |
C1—C2—C3 | 115.79 (12) | C16—C15—H15A | 110.00 |
C2—C3—C4 | 122.19 (12) | C16—C15—H15B | 110.00 |
C3—C4—C5 | 121.91 (13) | N2—C15—H15B | 110.00 |
C4—C5—C6 | 115.88 (12) | H15A—C15—H15B | 108.00 |
N2—C6—C1 | 106.42 (11) | N3—C16—H16B | 109.00 |
C1—C6—C5 | 121.97 (11) | C15—C16—H16A | 109.00 |
N2—C6—C5 | 131.60 (11) | C15—C16—H16B | 109.00 |
N1—C7—C8 | 112.37 (11) | H16A—C16—H16B | 108.00 |
C7—C8—C9 | 120.21 (12) | N3—C16—H16A | 109.00 |
C7—C8—C13 | 120.33 (11) | N3—C17—H17B | 110.00 |
C9—C8—C13 | 119.42 (12) | C18—C17—H17A | 110.00 |
C8—C9—C10 | 119.83 (13) | N3—C17—H17A | 110.00 |
C9—C10—C11 | 120.09 (14) | H17A—C17—H17B | 108.00 |
C10—C11—C12 | 120.31 (14) | C18—C17—H17B | 110.00 |
C11—C12—C13 | 119.80 (13) | C17—C18—H18A | 109.00 |
C8—C13—C12 | 120.55 (13) | C17—C18—H18B | 109.00 |
N1—C14—N2 | 110.43 (11) | C19—C18—H18B | 109.00 |
N2—C15—C16 | 109.17 (10) | H18A—C18—H18B | 108.00 |
N3—C16—C15 | 112.05 (11) | C19—C18—H18A | 109.00 |
N3—C17—C18 | 110.35 (13) | C18—C19—H19B | 109.00 |
C17—C18—C19 | 111.26 (15) | C20—C19—H19A | 109.00 |
C18—C19—C20 | 111.11 (15) | C20—C19—H19B | 109.00 |
C19—C20—C21 | 111.62 (16) | H19A—C19—H19B | 108.00 |
N3—C21—C20 | 110.29 (13) | C18—C19—H19A | 109.00 |
C3—C2—H2 | 122.00 | C19—C20—H20B | 109.00 |
C1—C2—H2 | 122.00 | C21—C20—H20A | 109.00 |
C2—C3—H3 | 119.00 | C19—C20—H20A | 109.00 |
C4—C3—H3 | 119.00 | H20A—C20—H20B | 108.00 |
C5—C4—H4 | 119.00 | C21—C20—H20B | 109.00 |
C3—C4—H4 | 119.00 | N3—C21—H21A | 110.00 |
C4—C5—H5 | 122.00 | N3—C21—H21B | 110.00 |
C6—C5—H5 | 122.00 | C20—C21—H21B | 110.00 |
N1—C7—H7B | 109.00 | H21A—C21—H21B | 108.00 |
C8—C7—H7A | 109.00 | C20—C21—H21A | 110.00 |
| | | |
C7—N1—C1—C2 | 0.3 (2) | C2—C1—C6—C5 | −0.22 (19) |
C14—N1—C1—C2 | 178.95 (13) | C2—C1—C6—N2 | −179.33 (11) |
C7—N1—C1—C6 | −177.80 (11) | N1—C1—C6—C5 | 178.07 (11) |
C14—N1—C1—C6 | 0.87 (14) | N1—C1—C2—C3 | −177.97 (12) |
C1—N1—C7—C8 | −81.97 (15) | C1—C2—C3—C4 | 0.25 (18) |
C14—N1—C7—C8 | 99.59 (14) | C2—C3—C4—C5 | 0.0 (2) |
C1—N1—C14—N2 | −0.34 (14) | C3—C4—C5—C6 | −0.36 (18) |
C7—N1—C14—N2 | 178.33 (11) | C4—C5—C6—C1 | 0.47 (18) |
C14—N2—C6—C1 | 0.86 (14) | C4—C5—C6—N2 | 179.33 (13) |
C14—N2—C15—C16 | 108.14 (14) | N1—C7—C8—C9 | 124.84 (14) |
C15—N2—C14—N1 | 178.64 (11) | N1—C7—C8—C13 | −57.66 (16) |
C15—N2—C6—C5 | 2.9 (2) | C13—C8—C9—C10 | 0.1 (2) |
C6—N2—C15—C16 | −73.07 (16) | C7—C8—C13—C12 | −177.40 (13) |
C6—N2—C14—N1 | −0.33 (15) | C7—C8—C9—C10 | 177.63 (14) |
C15—N2—C6—C1 | −178.11 (11) | C9—C8—C13—C12 | 0.1 (2) |
C14—N2—C6—C5 | −178.13 (13) | C8—C9—C10—C11 | 0.1 (3) |
C17—N3—C16—C15 | 59.98 (14) | C9—C10—C11—C12 | −0.5 (3) |
C17—N3—C21—C20 | −57.97 (17) | C10—C11—C12—C13 | 0.8 (2) |
C21—N3—C16—C15 | −176.38 (11) | C11—C12—C13—C8 | −0.6 (2) |
C16—N3—C17—C18 | −178.61 (12) | N2—C15—C16—N3 | 163.04 (10) |
C21—N3—C17—C18 | 58.75 (16) | N3—C17—C18—C19 | −56.70 (17) |
C16—N3—C21—C20 | 177.79 (13) | C17—C18—C19—C20 | 54.3 (2) |
N1—C1—C6—N2 | −1.04 (13) | C18—C19—C20—C21 | −53.7 (2) |
C6—C1—C2—C3 | −0.15 (18) | C19—C20—C21—N3 | 55.3 (2) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) x, y+1, z; (iii) −x+3/2, y−1/2, −z+3/2; (iv) −x+1, −y+2, −z+1; (v) x−1/2, −y+3/2, z−1/2; (vi) x, y−1, z; (vii) −x+3/2, y+1/2, −z+3/2; (viii) x−1/2, −y+3/2, z+1/2; (ix) −x+3/2, y+1/2, −z+1/2; (x) x+1/2, −y+3/2, z+1/2; (xi) x−1/2, −y+1/2, z+1/2; (xii) −x+3/2, y−1/2, −z+1/2; (xiii) x+1/2, −y+3/2, z−1/2; (xiv) x+1/2, −y+1/2, z−1/2. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3A···Cl2 | 0.915 (16) | 2.100 (15) | 3.0066 (13) | 170.5 (15) |
O1—H22···Cl1vi | 0.84 (2) | 2.35 (2) | 3.1919 (12) | 176 (2) |
O1—H23···Cl1i | 0.85 (2) | 2.33 (2) | 3.1722 (12) | 175 (2) |
C2—H2···Cl2vii | 0.93 | 2.81 | 3.6549 (14) | 152 |
C7—H7A···Cl1 | 0.97 | 2.80 | 3.6930 (15) | 153 |
C9—H9···Cl2vii | 0.93 | 2.75 | 3.6243 (15) | 158 |
C15—H15A···O1i | 0.97 | 2.57 | 3.2734 (18) | 129 |
C15—H15B···Cl2 | 0.97 | 2.79 | 3.5749 (15) | 139 |
Symmetry codes: (i) −x+1, −y+1, −z+1; (vi) x, y−1, z; (vii) −x+3/2, y+1/2, −z+3/2. |
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