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The title compound, C20H26Cl3N3O, was synthesized from 1-(4-chloro­benz­yl)benzimidazole and 1-(2-chloro­ethyl)pyrrol­id­ine hydro­chloride in dimethyl­formamide. The dihedral angle between the benzene ring and the benzimidazole ring system is 68.33 (8)°. The five-membered pyrrolidine ring has a slightly distorted envelope conformation. The crystal structure is stabilized by O—H...Cl, C—H...Cl, N—H...Cl and C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806054420/lh2272sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806054420/lh2272Isup2.hkl
Contains datablock I

CCDC reference: 633923

Key indicators

  • Single-crystal X-ray study
  • T = 296 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.038
  • wR factor = 0.105
  • Data-to-parameter ratio = 18.3

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C19
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 .... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.30 Ratio PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for N3 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 2
0 ALERT level A = In general: serious problem 1 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 3 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 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: 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-(4-Chlorobenzyl)-3-[2-(pyrrolidinium-1-yl)ethyl]benzimidazolium dichloride monohydrate top
Crystal data top
C20H24ClN32+·2Cl·H2OF(000) = 904
Mr = 430.79Dx = 1.341 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 31509 reflections
a = 15.3427 (8) Åθ = 1.4–27.2°
b = 6.8703 (2) ŵ = 0.45 mm1
c = 21.7329 (11) ÅT = 296 K
β = 111.355 (4)°Prism, colourless
V = 2133.56 (18) Å30.50 × 0.34 × 0.17 mm
Z = 4
Data collection top
Stoe IPDS-2
diffractometer
4634 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus3223 reflections with I > 2σ(I)
Plane graphite monochromatorRint = 0.061
Detector resolution: 6.67 pixels mm-1θmax = 27.2°, θmin = 1.4°
ω scansh = 1919
Absorption correction: integration
(XRED32; Stoe & Cie, 2002)
k = 88
Tmin = 0.808, Tmax = 0.928l = 2727
39631 measured reflections
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.105 w = 1/[σ2(Fo2) + (0.0666P)2]
where P = (Fo2 + 2Fc2)/3
S = 0.98(Δ/σ)max < 0.001
4634 reflectionsΔρmax = 0.24 e Å3
253 parametersΔρmin = 0.37 e Å3
0 restraintsExtinction correction: SHELXL97, FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0127 (13)
Special details top

Experimental. 13C-NMR (D2O): δ 22.68, 42.90, 50.34, 52.09, 54.68, 112.86, 114.00, 127.73, 129.25, 130.04, 131.11, 134.57, 141.74. Analysis calculated for C20H26N3OCl3: C 55.75, H 6.04, N 9.76%; found: C 55.63, H 5.58, N 9.80%. 1H-NMR (D2O): δ 1.5–2.1 (m, ring methylene, 4H), 3.0 (m, ring methylene, 2H), 3.4 (t, ring methylene, 2H), 4.0 (t, pyrrolidine-CH2CH2–,2H), 4.9 (t, pyrrolidine-CH2CH2–, 2H), 5.8 (s, PhCH2–, 2H), 6.8–7.8 (m, Ar—H, 8H), 9.7 (s, pyrrolidine-1H). 13C-NMR (D2O): δ 22.68, 42.90, 50.34, 52.09, 54.68, 112.86, 114.00, 127.73, 129.25, 130.04, 131.11, 134.57, 141.74. Analysis calculated for C20H26N3OCl3: C 55.75, H 6.04, N 9.76%; found: C 55.63, H 5.58, N 9.80%.

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
Cl10.92948 (4)0.58903 (9)0.25253 (3)0.0801 (2)
N10.60810 (9)0.12368 (18)0.19517 (6)0.0439 (4)
N20.45845 (9)0.09061 (19)0.13970 (6)0.0438 (4)
N30.20907 (10)0.1801 (2)0.03254 (7)0.0533 (4)
C10.54208 (11)0.1117 (2)0.13534 (8)0.0459 (5)
C20.47005 (11)0.0911 (2)0.20636 (7)0.0421 (4)
C30.40623 (11)0.0783 (2)0.23813 (8)0.0470 (5)
C40.44348 (13)0.0856 (2)0.30641 (8)0.0511 (5)
C50.53949 (12)0.1041 (2)0.34150 (8)0.0501 (5)
C60.60266 (12)0.1163 (2)0.31014 (8)0.0464 (5)
C70.56531 (10)0.1094 (2)0.24141 (7)0.0412 (4)
C80.70905 (11)0.1528 (2)0.21000 (9)0.0497 (5)
C90.76251 (11)0.0369 (2)0.22314 (8)0.0460 (5)
C100.83324 (12)0.0735 (3)0.28300 (9)0.0567 (5)
C110.88393 (13)0.2438 (3)0.29322 (9)0.0628 (6)
C120.86369 (12)0.3775 (3)0.24236 (9)0.0541 (5)
C130.79309 (13)0.3463 (3)0.18330 (9)0.0566 (6)
C140.74255 (12)0.1751 (3)0.17389 (8)0.0539 (5)
C150.37004 (11)0.0589 (2)0.08390 (8)0.0493 (5)
C160.30607 (12)0.2337 (3)0.07377 (8)0.0530 (5)
C170.19630 (15)0.1083 (4)0.03468 (9)0.0752 (7)
C180.09488 (19)0.1451 (6)0.07314 (14)0.1111 (12)
C190.0763 (2)0.3353 (6)0.0473 (2)0.1361 (15)
C200.13971 (16)0.3431 (4)0.02346 (13)0.0847 (9)
O10.55265 (15)0.2402 (3)0.03085 (9)0.0815 (6)
Cl20.66000 (4)0.64696 (8)0.03799 (3)0.0728 (2)
Cl30.17213 (4)0.15216 (8)0.10900 (3)0.0730 (2)
H10.552900.117200.096000.0550*
H30.342300.065700.214800.0560*
H3A0.191700.081900.053700.0640*
H40.403300.077800.329700.0610*
H50.561400.108300.387400.0600*
H60.666600.128400.333500.0560*
H8A0.717500.218100.173000.0600*
H8B0.734400.236400.248400.0600*
H100.846800.017900.316800.0680*
H110.931100.268500.333800.0750*
H130.779100.438700.149800.0680*
H140.694300.152800.133700.0650*
H15A0.383000.035800.044100.0590*
H15B0.339000.055400.092300.0590*
H16A0.327600.337200.052400.0640*
H16B0.307900.281300.116300.0640*
H17A0.235600.179600.053200.0900*
H17B0.210800.029300.033900.0900*
H18A0.056300.043000.065600.1330*
H18B0.082900.153000.120100.1330*
H19A0.089500.442100.071800.1630*
H19B0.011500.343600.051100.1630*
H20A0.171600.467600.033600.1020*
H20B0.104500.324900.052100.1020*
HW10.497 (2)0.261 (4)0.0138 (13)0.087 (9)*
HW20.582 (2)0.348 (5)0.0309 (15)0.103 (10)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0739 (3)0.0759 (3)0.0881 (4)0.0267 (3)0.0265 (3)0.0033 (3)
N10.0414 (6)0.0460 (7)0.0450 (7)0.0011 (5)0.0167 (5)0.0009 (5)
N20.0425 (6)0.0486 (7)0.0381 (6)0.0005 (5)0.0121 (5)0.0003 (5)
N30.0459 (7)0.0610 (8)0.0486 (7)0.0025 (6)0.0119 (6)0.0055 (6)
C10.0491 (8)0.0483 (8)0.0421 (8)0.0026 (6)0.0189 (7)0.0024 (6)
C20.0452 (8)0.0388 (7)0.0424 (7)0.0010 (6)0.0160 (6)0.0006 (6)
C30.0447 (8)0.0471 (8)0.0520 (9)0.0002 (6)0.0208 (7)0.0000 (7)
C40.0629 (10)0.0460 (8)0.0531 (9)0.0024 (7)0.0314 (8)0.0011 (7)
C50.0660 (10)0.0439 (8)0.0409 (8)0.0011 (7)0.0199 (7)0.0002 (6)
C60.0495 (8)0.0423 (8)0.0431 (8)0.0016 (6)0.0116 (7)0.0000 (6)
C70.0433 (7)0.0394 (7)0.0417 (7)0.0002 (6)0.0165 (6)0.0001 (6)
C80.0428 (8)0.0538 (9)0.0542 (9)0.0022 (7)0.0196 (7)0.0010 (7)
C90.0405 (8)0.0531 (9)0.0467 (8)0.0018 (6)0.0188 (6)0.0000 (7)
C100.0517 (9)0.0644 (10)0.0482 (9)0.0027 (8)0.0114 (7)0.0080 (8)
C110.0549 (10)0.0743 (12)0.0508 (9)0.0116 (9)0.0093 (8)0.0003 (9)
C120.0469 (8)0.0582 (10)0.0607 (10)0.0032 (7)0.0237 (8)0.0041 (8)
C130.0546 (9)0.0615 (10)0.0547 (10)0.0003 (8)0.0210 (8)0.0088 (8)
C140.0483 (9)0.0636 (10)0.0454 (8)0.0033 (7)0.0119 (7)0.0017 (7)
C150.0456 (8)0.0539 (9)0.0420 (8)0.0011 (7)0.0083 (7)0.0036 (7)
C160.0512 (9)0.0522 (9)0.0480 (8)0.0027 (7)0.0090 (7)0.0017 (7)
C170.0598 (11)0.1088 (17)0.0463 (9)0.0042 (11)0.0065 (8)0.0088 (10)
C180.0628 (14)0.176 (3)0.0695 (15)0.0141 (17)0.0055 (12)0.0042 (17)
C190.0754 (18)0.150 (3)0.135 (3)0.0316 (19)0.0189 (18)0.019 (2)
C200.0648 (13)0.0874 (16)0.0922 (16)0.0233 (11)0.0172 (12)0.0103 (12)
O10.0774 (11)0.0797 (12)0.0807 (10)0.0131 (10)0.0209 (9)0.0043 (8)
Cl20.0721 (3)0.0789 (3)0.0606 (3)0.0031 (2)0.0162 (2)0.0025 (2)
Cl30.0590 (3)0.0802 (3)0.0820 (3)0.0003 (2)0.0284 (2)0.0227 (3)
Geometric parameters (Å, º) top
Cl1—C121.737 (2)C17—C181.496 (4)
O1—HW10.81 (3)C18—C191.490 (6)
O1—HW20.87 (3)C19—C201.492 (5)
N1—C11.328 (2)C1—H10.9300
N1—C71.390 (2)C3—H30.9300
N1—C81.476 (2)C4—H40.9300
N2—C11.329 (2)C5—H50.9300
N2—C151.470 (2)C6—H60.9300
N2—C21.3938 (19)C8—H8A0.9700
N3—C171.486 (2)C8—H8B0.9700
N3—C201.508 (3)C10—H100.9300
N3—C161.477 (2)C11—H110.9300
N3—H3A0.9100C13—H130.9300
C2—C31.391 (2)C14—H140.9300
C2—C71.386 (2)C15—H15B0.9700
C3—C41.383 (2)C15—H15A0.9700
C4—C51.396 (3)C16—H16A0.9700
C5—C61.376 (3)C16—H16B0.9700
C6—C71.392 (2)C17—H17A0.9700
C8—C91.511 (2)C17—H17B0.9700
C9—C101.380 (2)C18—H18B0.9700
C9—C141.379 (2)C18—H18A0.9700
C10—C111.377 (3)C19—H19A0.9700
C11—C121.383 (3)C19—H19B0.9700
C12—C131.362 (3)C20—H20B0.9700
C13—C141.382 (3)C20—H20A0.9700
C15—C161.516 (3)
Cl1···C8i3.6279 (19)C6···H8B2.9200
Cl1···C11ii3.520 (2)C6···H16Biv2.8500
Cl2···O13.219 (2)C8···H62.9900
Cl2···O1iii3.151 (2)C13···H18Bvi3.0300
Cl2···C1i3.6451 (18)C13···H17Avi2.9300
Cl3···C163.603 (2)C13···H4iv2.9700
Cl3···N32.9965 (16)C14···H17Avi2.7600
Cl3···C153.5814 (19)C14···H4iv2.7900
Cl3···C6iv3.6243 (19)C15···H17A3.0600
Cl1···H18Bv2.9400C15···H17B2.8900
Cl2···H17Biii3.0000C15···H33.0300
Cl2···HW1iii2.34 (3)C17···H15B3.0500
Cl2···H15Aiii3.1500C17···H15A2.8000
Cl2···H16Avi2.9500H1···O12.8300
Cl2···H1i2.9000H1···Cl2x2.9000
Cl2···H5vii3.0800H1···O1vi2.7700
Cl2···H8Ai2.8900H1···HW1vi2.4300
Cl2···H132.8400H1···H15A2.5000
Cl2···HW22.35 (3)H1···H8A2.5700
Cl3···H19Bviii2.9400HW1···H1vi2.4300
Cl3···H10iv2.8600HW1···Cl2iii2.34 (3)
Cl3···H15B2.7900HW2···Cl22.35 (3)
Cl3···H20Ai3.0800H3···H16B2.5000
Cl3···H3A2.0900H3···C153.0300
Cl3···H6iv2.7800H3A···Cl32.0900
Cl3···H8Biv3.0000H3A···H15B2.3100
O1···C13.361 (3)H4···C13ix2.9700
O1···Cl2iii3.151 (2)H4···C14ix2.7900
O1···C15vi3.366 (3)H5···Cl2xii3.0800
O1···Cl23.219 (2)H5···H16Aiv2.5400
O1···H15Avi2.6000H6···C82.9900
O1···H142.5600H6···H16Biv2.5900
O1···H1vi2.7700H6···H8B2.5400
O1···H12.8300H6···Cl3ix2.7800
N1···C4ix3.2679 (19)H8A···H12.5700
N2···C5iv3.3661 (19)H8A···Cl2x2.8900
N3···Cl32.9965 (16)H8B···H62.5400
N1···H142.9000H8B···H102.3600
C1···C4ix3.471 (2)H8B···C62.9200
C1···O13.361 (3)H8B···Cl3ix3.0000
C1···C143.488 (3)H10···Cl3ix2.8600
C1···Cl2x3.6451 (18)H10···H8B2.3600
C2···C6iv3.424 (2)H13···Cl22.8400
C2···C5iv3.491 (2)H14···N12.9000
C3···C7iv3.260 (2)H14···C12.9700
C3···C163.502 (2)H14···O12.5600
C3···C6iv3.330 (2)H14···H17Avi2.3700
C4···C14ix3.453 (3)H15A···H12.5000
C4···C1iv3.471 (2)H15A···C172.8000
C4···C7iv3.421 (2)H15A···O1vi2.6000
C4···N1iv3.2679 (19)H15A···Cl2iii3.1500
C5···N2ix3.3661 (19)H15B···H3A2.3100
C5···C16iv3.508 (3)H15B···C5iv3.0100
C5···C2ix3.491 (2)H15B···C173.0500
C5···C15ix3.561 (2)H15B···C33.0900
C6···Cl3ix3.6243 (19)H15B···Cl32.7900
C6···C16iv3.559 (2)H15B···C6iv3.0000
C6···C3ix3.330 (2)H16A···H17A2.4600
C6···C2ix3.424 (2)H16A···H20A2.4500
C7···C4ix3.421 (2)H16A···Cl2vi2.9500
C7···C3ix3.260 (2)H16A···C5ix3.0700
C8···Cl1x3.6279 (19)H16A···H5ix2.5400
C11···Cl1xi3.520 (2)H16B···C22.8600
C14···C17vi3.509 (3)H16B···C32.8800
C14···C13.488 (3)H16B···H32.5000
C14···C4iv3.453 (3)H16B···H20A2.5500
C15···Cl33.5814 (19)H16B···H6ix2.5900
C15···O1vi3.366 (3)H16B···C6ix2.8500
C15···C5iv3.561 (2)H17A···C13vi2.9300
C16···C5ix3.508 (3)H17A···H16A2.4600
C16···C33.502 (2)H17A···C153.0600
C16···Cl33.603 (2)H17A···C14vi2.7600
C16···C6ix3.559 (2)H17A···H14vi2.3700
C17···C14vi3.509 (3)H17B···C152.8900
C1···H142.9700H17B···Cl2iii3.0000
C2···H16B2.8600H18B···Cl1xiii2.9400
C3···H15B3.0900H18B···C13vi3.0300
C3···H16B2.8800H19B···Cl3viii2.9400
C5···H16Aiv3.0700H20A···Cl3x3.0800
C5···H15Bix3.0100H20A···H16A2.4500
C6···H15Bix3.0000H20A···H16B2.5500
HW1—O1—HW2108 (3)C4—C5—H5119.00
C1—N1—C8125.99 (14)C6—C5—H5119.00
C7—N1—C8125.88 (13)C7—C6—H6122.00
C1—N1—C7108.11 (14)C5—C6—H6122.00
C1—N2—C2108.23 (13)N1—C8—H8A109.00
C1—N2—C15125.63 (13)N1—C8—H8B109.00
C2—N2—C15126.03 (14)C9—C8—H8B109.00
C16—N3—C17114.97 (16)H8A—C8—H8B108.00
C16—N3—C20113.67 (16)C9—C8—H8A109.00
C17—N3—C20106.49 (16)C11—C10—H10120.00
C17—N3—H3A107.00C9—C10—H10120.00
C20—N3—H3A107.00C10—C11—H11120.00
C16—N3—H3A107.00C12—C11—H11120.00
N1—C1—N2110.43 (14)C14—C13—H13121.00
N2—C2—C7106.35 (14)C12—C13—H13121.00
N2—C2—C3132.00 (15)C9—C14—H14119.00
C3—C2—C7121.66 (14)C13—C14—H14119.00
C2—C3—C4116.08 (16)N2—C15—H15B109.00
C3—C4—C5122.06 (18)C16—C15—H15A109.00
C4—C5—C6121.91 (15)C16—C15—H15B109.00
C5—C6—C7116.14 (16)H15A—C15—H15B108.00
N1—C7—C6130.93 (15)N2—C15—H15A109.00
C2—C7—C6122.17 (15)N3—C16—H16B110.00
N1—C7—C2106.87 (13)C15—C16—H16A110.00
N1—C8—C9112.25 (12)N3—C16—H16A110.00
C10—C9—C14118.83 (16)H16A—C16—H16B108.00
C8—C9—C10121.45 (15)C15—C16—H16B110.00
C8—C9—C14119.69 (15)N3—C17—H17A111.00
C9—C10—C11120.71 (17)N3—C17—H17B111.00
C10—C11—C12119.09 (18)C18—C17—H17B111.00
Cl1—C12—C11120.21 (15)H17A—C17—H17B109.00
Cl1—C12—C13118.53 (15)C18—C17—H17A111.00
C11—C12—C13121.26 (19)C17—C18—H18B111.00
C12—C13—C14118.96 (18)C19—C18—H18A111.00
C9—C14—C13121.12 (16)C19—C18—H18B111.00
N2—C15—C16110.90 (13)H18A—C18—H18B109.00
N3—C16—C15110.29 (15)C17—C18—H18A111.00
N3—C17—C18103.4 (2)C18—C19—H19B111.00
C17—C18—C19103.9 (3)C20—C19—H19A111.00
C18—C19—C20106.1 (3)C18—C19—H19A110.00
N3—C20—C19105.8 (2)H19A—C19—H19B109.00
N2—C1—H1125.00C20—C19—H19B110.00
N1—C1—H1125.00N3—C20—H20A111.00
C2—C3—H3122.00N3—C20—H20B111.00
C4—C3—H3122.00C19—C20—H20B111.00
C5—C4—H4119.00H20A—C20—H20B109.00
C3—C4—H4119.00C19—C20—H20A111.00
C7—N1—C1—N20.07 (17)N2—C2—C7—N11.28 (15)
C8—N1—C1—N2178.32 (13)C3—C2—C7—N1178.39 (13)
C7—N1—C8—C985.98 (18)N2—C2—C7—C6179.58 (13)
C1—N1—C7—C6178.96 (15)C2—C3—C4—C50.2 (2)
C1—N1—C7—C20.86 (16)C3—C4—C5—C60.1 (2)
C8—N1—C7—C2177.53 (13)C4—C5—C6—C70.1 (2)
C8—N1—C7—C60.6 (2)C5—C6—C7—C20.1 (2)
C1—N1—C8—C995.91 (18)C5—C6—C7—N1177.79 (14)
C15—N2—C1—N1175.45 (13)N1—C8—C9—C1462.7 (2)
C2—N2—C1—N10.75 (16)N1—C8—C9—C10119.25 (18)
C15—N2—C2—C35.5 (2)C8—C9—C14—C13176.98 (18)
C1—N2—C2—C71.26 (16)C8—C9—C10—C11177.25 (18)
C1—N2—C2—C3178.36 (15)C14—C9—C10—C110.8 (3)
C2—N2—C15—C1672.28 (19)C10—C9—C14—C131.2 (3)
C1—N2—C15—C16112.18 (17)C9—C10—C11—C120.7 (3)
C15—N2—C2—C7174.92 (13)C10—C11—C12—C131.9 (3)
C20—N3—C16—C15176.51 (16)C10—C11—C12—Cl1177.35 (16)
C16—N3—C17—C18157.1 (2)C11—C12—C13—C141.6 (3)
C17—N3—C16—C1560.4 (2)Cl1—C12—C13—C14177.66 (16)
C20—N3—C17—C1830.3 (3)C12—C13—C14—C90.1 (3)
C17—N3—C20—C1910.9 (3)N2—C15—C16—N3162.79 (13)
C16—N3—C20—C19138.5 (2)N3—C17—C18—C1938.2 (3)
N2—C2—C3—C4179.36 (14)C17—C18—C19—C2031.8 (3)
C3—C2—C7—C60.1 (2)C18—C19—C20—N313.0 (3)
C7—C2—C3—C40.2 (2)
Symmetry codes: (i) x, y+1, z; (ii) x+2, y+1/2, z+1/2; (iii) x+1, y+1, z; (iv) x+1, y+1/2, z+1/2; (v) x+1, y+1/2, z+1/2; (vi) x+1, y, z; (vii) x, y+1/2, z1/2; (viii) x, y, z; (ix) x+1, y1/2, z+1/2; (x) x, y1, z; (xi) x+2, y1/2, z+1/2; (xii) x, y+1/2, z+1/2; (xiii) x1, y+1/2, z1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—HW1···Cl2iii0.81 (3)2.34 (3)3.151 (2)174 (3)
O1—HW2···Cl20.87 (3)2.35 (3)3.219 (2)176 (3)
N3—H3A···Cl30.912.092.9965 (16)172
C6—H6···Cl3ix0.932.783.6243 (19)152
C14—H14···O10.932.563.429 (3)156
C15—H15B···Cl30.972.793.5814 (19)139
Symmetry codes: (iii) x+1, y+1, z; (ix) x+1, y1/2, z+1/2.
 

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