1-Benz­yl-3-[2-(1-piperidinio)eth­yl]benzimidazolium dichloride monohydrate

The title compound, C₂₁H₂₇N₃²⁺·2Cl⁻·H₂O, 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.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](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

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Computing details

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

Crystal data

C21H27N3^2+·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) Å^3	0.78 × 0.49 × 0.18 mm
Z = 4

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.078	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ^2(Fo^2) + (0.0383P)^2 + 0.7441P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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···O1^i	3.1722 (12)	C17···H13^i	3.0700
Cl1···O1^ii	3.1919 (12)	C17···H15A	2.7900
Cl2···N3	3.0066 (13)	C17···H15B	3.0700
Cl2···C16	3.6010 (14)	C19···H18B^ix	3.0500
Cl2···C9^iii	3.6243 (15)	H2···C7	3.0000
Cl2···C15	3.5749 (15)	H2···H7B	2.5900
Cl1···H21B^iv	3.0900	H2···Cl2^vii	2.8100
Cl1···H23^i	2.33 (2)	H3···H23^vii	2.5800
Cl1···H3^v	3.0500	H3···Cl1^x	3.0500
Cl1···H7A	2.8000	H3···H16A^iii	2.4600
Cl1···H12^ii	3.0000	H3A···H15B	2.3600
Cl1···H15A^i	3.1300	H3A···H20B	2.5400
Cl1···H24	2.864 (16)	H3A···H18A	2.5000
Cl1···H17B^i	2.9100	H3A···Cl2	2.100 (15)
Cl1···H22^ii	2.35 (2)	H4···H13^vii	2.5200
Cl1···H16A^iv	3.0000	H4···C12^vii	3.0700
Cl2···H5	3.1300	H4···C13^vii	2.8400
Cl2···H15B	2.7900	H5···C15	3.0200
Cl2···H2^iii	2.8100	H5···Cl2	3.1300
Cl2···H7B^iii	3.0200	H5···H16B	2.5400
Cl2···H3A	2.100 (15)	H7A···H12^ii	2.5800
Cl2···H9^iii	2.7500	H7A···Cl1	2.8000
O1···C14	3.1626 (17)	H7A···H24	2.5300
O1···Cl1^i	3.1722 (12)	H7B···H2	2.5900
O1···C15^i	3.2734 (18)	H7B···H9	2.3400
O1···Cl1^vi	3.1919 (12)	H7B···C2	2.9600
O1···H13	2.7700	H7B···Cl2^vii	3.0200
O1···H24^i	2.805 (16)	H9···H7B	2.3400
O1···H16A^i	2.8000	H9···Cl2^vii	2.7500
O1···H15A^i	2.5700	H11···H20B^xi	2.3500
O1···H24	2.648 (15)	H12···Cl1^vi	3.0000
N1···N2	2.1864 (15)	H12···H7A^vi	2.5800
N1···C4^vii	3.2982 (17)	H13···H4^iii	2.5200
N2···C3^iii	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···C17^i	3.0700
C1···C5^vii	3.2347 (17)	H13···H17A^i	2.3100
C1···C4^vii	3.4640 (18)	H15A···C17	2.7900
C1···C6^vii	3.5960 (17)	H15A···H17B	2.2500
C2···C16^iii	3.5013 (18)	H15A···O1^i	2.5700
C2···C6^vii	3.4336 (18)	H15A···H24	2.5200
C2···C5^vii	3.3221 (18)	H15A···Cl1^i	3.1300
C3···N2^vii	3.3364 (17)	H15B···C3^iii	2.9700
C3···C6^vii	3.5129 (18)	H15B···Cl2	2.7900
C3···C16^iii	3.4099 (18)	H15B···C17	3.0700
C3···C15^vii	3.4983 (18)	H15B···H3A	2.3600
C4···C13^vii	3.446 (2)	H15B···C2^iii	2.9300
C4···C14^iii	3.4895 (18)	H15B···C5	3.0700
C4···C1^iii	3.4640 (18)	H16A···H17A	2.5100
C4···N1^iii	3.2982 (17)	H16A···C3^vii	2.9500
C5···C16	3.4994 (18)	H16A···H3^vii	2.4600
C5···C2^iii	3.3221 (18)	H16A···H21B	2.4600
C5···C1^iii	3.2347 (17)	H16A···Cl1^iv	3.0000
C6···C3^iii	3.5129 (18)	H16A···O1^i	2.8000
C6···C2^iii	3.4336 (18)	H16A···H22^i	2.5000
C6···C1^iii	3.5960 (17)	H16B···C5	2.8800
C9···Cl2^vii	3.6243 (15)	H16B···C6	2.8200
C13···C17^i	3.442 (2)	H16B···C2^vii	2.7800
C13···C14	3.513 (2)	H16B···H21A	2.3700
C13···C4^iii	3.446 (2)	H16B···C3^vii	2.9900
C14···Cl1	3.5484 (14)	H16B···H5	2.5400
C14···O1	3.1626 (17)	H17A···H13^i	2.3100
C14···C4^vii	3.4895 (18)	H17A···C12^i	3.0700
C14···C13	3.513 (2)	H17A···C13^i	2.7300
C15···Cl2	3.5749 (15)	H17A···H21B	2.5300
C15···C3^iii	3.4983 (18)	H17A···H16A	2.5100
C15···O1^i	3.2734 (18)	H17B···C15	2.6100
C16···C5	3.4994 (18)	H17B···H15A	2.2500
C16···C3^vii	3.4099 (18)	H17B···Cl1^i	2.9100
C16···C2^vii	3.5013 (18)	H18A···H3A	2.5000
C16···Cl2	3.6010 (14)	H18B···C19^xii	3.0500
C17···C13^i	3.442 (2)	H20A···C9^xiii	2.9100
C2···H16B^iii	2.7800	H20A···C10^xiii	2.9200
C2···H15B^vii	2.9300	H20B···H3A	2.5400
C2···H7B	2.9600	H20B···H11^xiv	2.3500
C3···H16B^iii	2.9900	H21A···C9^vii	2.9800
C3···H15B^vii	2.9700	H21A···H16B	2.3700
C3···H16A^iii	2.9500	H21B···H17A	2.5300
C5···H16B	2.8800	H21B···Cl1^iv	3.0900
C5···H15B	3.0700	H21B···H16A	2.4600
C6···H16B	2.8200	H22···H16A^i	2.5000
C7···H2	3.0000	H22···Cl1^vi	2.35 (2)
C9···H20A^viii	2.9100	H23···H24^i	2.48 (3)
C9···H21A^iii	2.9800	H23···Cl1^i	2.33 (2)
C10···H20A^viii	2.9200	H23···H3^iii	2.5800
C12···H4^iii	3.0700	H24···H23^i	2.48 (3)
C12···H17A^i	3.0700	H24···Cl1	2.864 (16)
C13···H4^iii	2.8400	H24···O1	2.648 (15)
C13···H17A^i	2.7300	H24···H7A	2.5300
C14···H13	2.9800	H24···H15A	2.5200
C15···H5	3.0200	H24···O1^i	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)

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···Cl1^vi	0.84 (2)	2.35 (2)	3.1919 (12)	176 (2)
O1—H23···Cl1^i	0.85 (2)	2.33 (2)	3.1722 (12)	175 (2)
C2—H2···Cl2^vii	0.93	2.81	3.6549 (14)	152
C7—H7A···Cl1	0.97	2.80	3.6930 (15)	153
C9—H9···Cl2^vii	0.93	2.75	3.6243 (15)	158
C15—H15A···O1^i	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.