1,3-Bis(4-methyl­benz­yl)benzimidazolium chloride monohydrate

The cation in the title compound, C₂₃H₂₃N₂⁺·Cl⁻·H₂O, features a benzimidazole ring connected to two 4-methyl­benzyl rings via methyl­ene bridges. The crystal structure is stabilized by C—H...O, C—H...Cl and O—H...Cl hydrogen-bonding inter­actions, leading to a three-dimensional framework.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.059
• wR factor = 0.160
• Data-to-parameter ratio = 18.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.96
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C10    -   C11     ..       5.35 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C19    -   C20     ..       5.35 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C19
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         C9
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C12
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C17
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C20
PLAT355_ALERT_3_C Long    O-H Bond (0.82A)   O1     -   H101   ...       1.02 Ang.
PLAT790_ALERT_4_C Centre of Gravity not Within Unit Cell: Resd.  #          3
              Cl

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
  11 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
   7 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 ALERT type 3 Indicator that the structure quality may be low
   1 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).

1,3-Bis(4-methylbenzyl)benzimidazolium chloride monohydrate

Crystal data

C23H23N2^+·Cl^−·H2O	Z = 2
Mr = 380.90	F(000) = 404
Triclinic, P1	Dx = 1.214 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.3636 (8) Å	Cell parameters from 40476 reflections
b = 9.4834 (8) Å	θ = 2.3–28.1°
c = 12.6509 (12) Å	µ = 0.20 mm^−1
α = 75.558 (7)°	T = 296 K
β = 82.798 (7)°	Prism, colourless
γ = 73.581 (7)°	0.58 × 0.55 × 0.52 mm
V = 1041.70 (17) Å^3

Data collection

Stoe IPDS2 diffractometer	4724 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	3043 reflections with I > 2σ(I)
Plane graphite monochromator	Rint = 0.060
Detector resolution: 6.67 pixels mm^-1	θmax = 27.7°, θmin = 2.5°
ω scans	h = −12→12
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −12→12
Tmin = 0.894, Tmax = 0.904	l = −16→16
23747 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)] = 0.059	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.160	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0755P)^2 + 0.1339P] where P = (Fo^2 + 2Fc^2)/3
4724 reflections	(Δ/σ)max < 0.001
254 parameters	Δρmax = 0.35 e Å^−3
0 restraints	Δρmin = −0.17 e Å^−3

Special details

Experimental. ¹H NMR (DMSO-d₆, δ, p.p.m.): 2.20 (s, –CH₃, 6H), 5.67 (s, –CH₂–, 4H), 7.13–7.90 (m, Ar—H, 12H), 10.16 (s, 2CH, 1H); ¹³C NMR (DMSO-d₆, δ, p.p.m.): 21.19, 50.26, 114.53, 127.19, 128.85, 130.01, 131.45, 138.67, 143.03.

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	0.0847 (2)	0.22227 (19)	0.62537 (14)	0.0684 (6)
N2	0.2190 (2)	0.3738 (2)	0.63237 (13)	0.0690 (6)
C1	−0.0153 (2)	0.3589 (2)	0.63699 (15)	0.0643 (7)
C2	−0.1697 (3)	0.4034 (3)	0.64205 (19)	0.0777 (8)
C3	−0.2332 (3)	0.5492 (3)	0.6523 (2)	0.0883 (9)
C4	−0.1475 (3)	0.6458 (3)	0.6560 (2)	0.0871 (9)
C5	0.0052 (3)	0.6026 (3)	0.65065 (18)	0.0775 (8)
C6	0.0707 (2)	0.4551 (2)	0.64078 (15)	0.0648 (7)
C7	0.2215 (3)	0.2375 (3)	0.62300 (17)	0.0722 (7)
C8	0.3514 (3)	0.4229 (3)	0.64242 (19)	0.0819 (9)
C9	0.3868 (3)	0.3852 (3)	0.7614 (2)	0.0758 (8)
C10	0.3251 (4)	0.4858 (3)	0.8266 (3)	0.1038 (11)
C11	0.3480 (4)	0.4440 (4)	0.9371 (3)	0.1095 (14)
C12	0.4335 (3)	0.3052 (4)	0.9854 (2)	0.0946 (10)
C13	0.4992 (4)	0.2089 (4)	0.9184 (3)	0.1013 (11)
C14	0.4757 (3)	0.2478 (3)	0.8080 (2)	0.0947 (10)
C15	0.4534 (5)	0.2632 (6)	1.1064 (3)	0.1347 (18)
C16	0.0464 (3)	0.0819 (3)	0.6238 (2)	0.0789 (8)
C17	0.0268 (3)	−0.0101 (2)	0.73839 (19)	0.0710 (7)
C18	−0.1100 (3)	−0.0316 (4)	0.7819 (3)	0.0998 (11)
C19	−0.1244 (4)	−0.1128 (4)	0.8877 (3)	0.1144 (14)
C20	−0.0058 (3)	−0.1767 (3)	0.9532 (2)	0.0880 (10)
C21	0.1287 (3)	−0.1542 (3)	0.9085 (2)	0.0949 (10)
C22	0.1461 (3)	−0.0734 (3)	0.8030 (2)	0.0930 (10)
C23	−0.0227 (5)	−0.2640 (4)	1.0689 (3)	0.1264 (14)
O1	0.4969 (3)	0.0557 (3)	0.35220 (17)	0.1092 (9)
Cl1	0.33838 (7)	−0.18318 (7)	0.50116 (6)	0.0923 (3)
H2	−0.22670	0.33880	0.63870	0.0930*
H3	−0.33660	0.58430	0.65700	0.1060*
H4	−0.19580	0.74380	0.66240	0.1050*
H5	0.06160	0.66800	0.65340	0.0930*
H7	0.30810	0.16200	0.61570	0.0870*
H8A	0.33300	0.53080	0.61330	0.0980*
H8B	0.43580	0.37260	0.60050	0.0980*
H10	0.26790	0.58190	0.79640	0.1250*
H11	0.30360	0.51280	0.98030	0.1320*
H13	0.56110	0.11500	0.94780	0.1210*
H14	0.52120	0.17930	0.76480	0.1140*
H15A	0.46580	0.15660	1.13290	0.2020*
H15B	0.36700	0.31690	1.14320	0.2020*
H15C	0.54000	0.28930	1.12040	0.2020*
H16A	0.12490	0.02230	0.58310	0.0950*
H16B	−0.04520	0.10710	0.58680	0.0950*
H18	−0.19280	0.00880	0.73980	0.1200*
H19	−0.21790	−0.12480	0.91580	0.1370*
H21	0.21150	−0.19470	0.95070	0.1140*
H22	0.23980	−0.06160	0.77530	0.1120*
H23A	−0.01470	−0.36720	1.06900	0.1900*
H23B	−0.11850	−0.22070	1.10100	0.1900*
H23C	0.05430	−0.25980	1.11060	0.1900*
H101	0.494 (4)	0.145 (5)	0.385 (3)	0.139 (13)*
H102	0.432 (5)	0.028 (5)	0.398 (4)	0.144 (16)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
N1	0.0768 (11)	0.0578 (9)	0.0633 (10)	−0.0041 (8)	−0.0054 (8)	−0.0153 (7)
N2	0.0721 (11)	0.0678 (10)	0.0578 (9)	−0.0096 (8)	0.0003 (8)	−0.0094 (8)
C1	0.0744 (13)	0.0590 (11)	0.0498 (10)	−0.0038 (9)	−0.0046 (8)	−0.0096 (8)
C2	0.0765 (14)	0.0781 (14)	0.0721 (13)	−0.0072 (11)	−0.0072 (11)	−0.0187 (11)
C3	0.0775 (15)	0.0870 (17)	0.0871 (16)	0.0075 (13)	−0.0076 (12)	−0.0275 (13)
C4	0.0988 (19)	0.0660 (13)	0.0833 (15)	0.0060 (13)	−0.0043 (13)	−0.0250 (12)
C5	0.0962 (17)	0.0619 (12)	0.0669 (13)	−0.0087 (11)	−0.0052 (11)	−0.0147 (10)
C6	0.0781 (13)	0.0594 (11)	0.0465 (10)	−0.0068 (9)	−0.0021 (8)	−0.0065 (8)
C7	0.0770 (14)	0.0664 (12)	0.0618 (12)	−0.0031 (10)	−0.0014 (10)	−0.0133 (9)
C8	0.0796 (15)	0.0874 (16)	0.0716 (14)	−0.0241 (12)	0.0088 (11)	−0.0089 (12)
C9	0.0683 (13)	0.0758 (14)	0.0821 (15)	−0.0227 (11)	0.0048 (10)	−0.0160 (11)
C10	0.109 (2)	0.0867 (18)	0.115 (2)	−0.0056 (15)	−0.0230 (17)	−0.0363 (16)
C11	0.107 (2)	0.131 (3)	0.095 (2)	−0.0113 (19)	−0.0132 (16)	−0.0525 (19)
C12	0.0859 (17)	0.127 (2)	0.0782 (16)	−0.0404 (17)	−0.0010 (13)	−0.0241 (16)
C13	0.108 (2)	0.0926 (19)	0.0906 (19)	−0.0141 (15)	−0.0144 (15)	−0.0073 (15)
C14	0.1008 (19)	0.0847 (17)	0.0822 (17)	0.0013 (14)	−0.0029 (14)	−0.0197 (13)
C15	0.127 (3)	0.208 (4)	0.0819 (19)	−0.074 (3)	−0.0032 (18)	−0.023 (2)
C16	0.0913 (16)	0.0649 (12)	0.0790 (14)	−0.0071 (11)	−0.0098 (11)	−0.0265 (11)
C17	0.0791 (14)	0.0557 (11)	0.0777 (13)	−0.0093 (10)	−0.0053 (11)	−0.0235 (10)
C18	0.0836 (17)	0.100 (2)	0.120 (2)	−0.0316 (15)	−0.0137 (15)	−0.0199 (17)
C19	0.095 (2)	0.119 (2)	0.127 (3)	−0.0489 (19)	0.0120 (19)	−0.009 (2)
C20	0.0978 (18)	0.0733 (15)	0.0907 (17)	−0.0245 (13)	0.0103 (14)	−0.0200 (13)
C21	0.0894 (18)	0.0917 (17)	0.0882 (17)	−0.0170 (14)	−0.0060 (13)	0.0001 (14)
C22	0.0734 (15)	0.0909 (17)	0.0947 (18)	−0.0133 (12)	0.0018 (13)	0.0025 (14)
C23	0.154 (3)	0.112 (2)	0.098 (2)	−0.042 (2)	0.027 (2)	−0.0050 (18)
O1	0.1191 (17)	0.1150 (17)	0.0761 (12)	−0.0124 (13)	−0.0001 (12)	−0.0134 (12)
Cl1	0.0806 (4)	0.0808 (4)	0.1266 (6)	−0.0275 (3)	0.0139 (3)	−0.0460 (4)

Geometric parameters (Å, º)

O1—H102	0.84 (5)	C20—C21	1.366 (4)
O1—H101	1.02 (5)	C20—C23	1.505 (4)
N1—C1	1.397 (3)	C21—C22	1.379 (4)
N1—C7	1.325 (4)	C2—H2	0.9300
N1—C16	1.479 (3)	C3—H3	0.9300
N2—C6	1.390 (3)	C4—H4	0.9300
N2—C7	1.321 (3)	C5—H5	0.9300
N2—C8	1.472 (4)	C7—H7	0.9300
C1—C2	1.385 (4)	C8—H8A	0.9700
C1—C6	1.389 (3)	C8—H8B	0.9700
C2—C3	1.374 (4)	C10—H10	0.9300
C3—C4	1.390 (4)	C11—H11	0.9300
C4—C5	1.369 (4)	C13—H13	0.9300
C5—C6	1.390 (3)	C14—H14	0.9300
C8—C9	1.514 (3)	C15—H15B	0.9600
C9—C14	1.366 (4)	C15—H15A	0.9600
C9—C10	1.373 (4)	C15—H15C	0.9600
C10—C11	1.381 (5)	C16—H16B	0.9700
C11—C12	1.369 (5)	C16—H16A	0.9700
C12—C13	1.367 (5)	C18—H18	0.9300
C12—C15	1.504 (4)	C19—H19	0.9300
C13—C14	1.382 (4)	C21—H21	0.9300
C16—C17	1.513 (3)	C22—H22	0.9300
C17—C18	1.379 (4)	C23—H23C	0.9600
C17—C22	1.372 (4)	C23—H23A	0.9600
C18—C19	1.379 (5)	C23—H23B	0.9600
C19—C20	1.374 (5)
Cl1···O1	3.155 (3)	H2···H16B	2.5400
Cl1···C16	3.633 (3)	H2···Cl1^iii	3.0100
Cl1···O1^i	3.189 (3)	H3···H101^v	2.5300
Cl1···H16A	2.6700	H4···O1^v	2.9200
Cl1···H102	2.43 (5)	H5···C8	3.0500
Cl1···H8A^ii	2.7400	H5···H8A	2.5600
Cl1···H2^iii	3.0100	H7···H8B	2.5600
Cl1···H8B^i	2.7700	H7···H16A	2.5700
Cl1···H16B^iii	2.9200	H7···O1^i	2.3200
Cl1···H101^i	2.41 (4)	H8A···H5	2.5600
O1···C7^i	3.227 (4)	H8A···C5	2.9500
O1···C15^iv	3.244 (5)	H8A···H10	2.4500
O1···Cl1	3.155 (3)	H8A···Cl1^xi	2.7400
O1···Cl1^i	3.189 (3)	H8B···H7	2.5600
O1···H22^i	2.7800	H8B···H14	2.4500
O1···H7^i	2.3200	H8B···Cl1^i	2.7700
O1···H15A^iv	2.7200	H10···H8A	2.4500
O1···H4^v	2.9200	H10···C21^xi	3.0700
N1···N2	2.183 (3)	H11···H15B	2.4100
N2···N1	2.183 (3)	H11···C21^xi	3.0800
C1···C6^v	3.546 (3)	H13···H15A	2.4800
C1···C5^v	3.557 (3)	H14···H8B	2.4500
C2···C6^v	3.597 (3)	H15A···H19^ix	2.5900
C3···C7^v	3.571 (3)	H15A···O1^vi	2.7200
C4···C7^v	3.521 (3)	H15A···H13	2.4800
C5···C1^v	3.557 (3)	H15B···H11	2.4100
C6···C2^v	3.597 (3)	H15B···C4^vii	3.0900
C6···C1^v	3.546 (3)	H15C···C10^viii	3.0100
C7···C22	3.435 (4)	H15C···C11^viii	2.9000
C7···C3^v	3.571 (3)	H15C···H21^x	2.3900
C7···C14	3.577 (4)	H15C···C21^x	3.0200
C7···O1^i	3.227 (4)	H16A···H7	2.5700
C7···C4^v	3.521 (3)	H16A···Cl1	2.6700
C14···C7	3.577 (4)	H16B···H2	2.5400
C15···O1^vi	3.244 (5)	H16B···C2	2.9400
C16···Cl1	3.633 (3)	H16B···Cl1^iii	2.9200
C22···C7	3.435 (4)	H16B···H18	2.3800
C2···H16B	2.9400	H18···H16B	2.3800
C4···H15B^vii	3.0900	H19···H15A^ix	2.5900
C5···H8A	2.9500	H19···C15^ix	2.9400
C7···H22	2.9800	H19···C12^ix	2.9700
C8···H5	3.0500	H19···H23B	2.4900
C10···H15C^viii	3.0100	H21···C15^x	3.0500
C11···H15C^viii	2.9000	H21···H15C^x	2.3900
C12···H19^ix	2.9700	H21···H23C	2.4100
C15···H19^ix	2.9400	H22···C7	2.9800
C15···H21^x	3.0500	H22···O1^i	2.7800
C16···H2	3.0200	H23B···H19	2.4900
C21···H10^ii	3.0700	H23C···H21	2.4100
C21···H11^ii	3.0800	H101···Cl1^i	2.41 (4)
C21···H15C^x	3.0200	H101···H3^v	2.5300
H2···C16	3.0200	H102···Cl1	2.43 (5)
H101—O1—H102	93 (4)	C5—C4—H4	119.00
C1—N1—C7	107.71 (19)	C3—C4—H4	119.00
C1—N1—C16	126.6 (2)	C4—C5—H5	122.00
C7—N1—C16	125.6 (2)	C6—C5—H5	122.00
C6—N2—C8	126.97 (19)	N1—C7—H7	124.00
C6—N2—C7	107.9 (2)	N2—C7—H7	124.00
C7—N2—C8	124.9 (2)	N2—C8—H8B	110.00
N1—C1—C6	106.36 (17)	C9—C8—H8A	110.00
C2—C1—C6	122.57 (19)	C9—C8—H8B	110.00
N1—C1—C2	131.1 (2)	H8A—C8—H8B	108.00
C1—C2—C3	115.6 (2)	N2—C8—H8A	110.00
C2—C3—C4	122.0 (3)	C9—C10—H10	120.00
C3—C4—C5	122.7 (3)	C11—C10—H10	120.00
C4—C5—C6	115.9 (2)	C12—C11—H11	119.00
N2—C6—C1	106.75 (17)	C10—C11—H11	119.00
C1—C6—C5	121.3 (2)	C14—C13—H13	119.00
N2—C6—C5	132.0 (2)	C12—C13—H13	119.00
N1—C7—N2	111.2 (2)	C9—C14—H14	120.00
N2—C8—C9	109.9 (2)	C13—C14—H14	119.00
C8—C9—C14	120.9 (2)	C12—C15—H15B	109.00
C10—C9—C14	118.2 (3)	C12—C15—H15C	110.00
C8—C9—C10	120.9 (3)	C12—C15—H15A	109.00
C9—C10—C11	119.9 (3)	H15A—C15—H15C	109.00
C10—C11—C12	122.5 (3)	H15B—C15—H15C	109.00
C11—C12—C13	116.8 (3)	H15A—C15—H15B	109.00
C13—C12—C15	122.4 (4)	N1—C16—H16A	109.00
C11—C12—C15	120.8 (3)	C17—C16—H16A	109.00
C12—C13—C14	121.6 (3)	C17—C16—H16B	109.00
C9—C14—C13	121.1 (3)	N1—C16—H16B	109.00
N1—C16—C17	111.35 (19)	H16A—C16—H16B	108.00
C16—C17—C18	121.8 (3)	C19—C18—H18	120.00
C16—C17—C22	120.4 (2)	C17—C18—H18	120.00
C18—C17—C22	117.9 (2)	C18—C19—H19	119.00
C17—C18—C19	120.2 (3)	C20—C19—H19	119.00
C18—C19—C20	122.5 (3)	C22—C21—H21	119.00
C19—C20—C23	122.2 (3)	C20—C21—H21	119.00
C21—C20—C23	121.4 (3)	C17—C22—H22	120.00
C19—C20—C21	116.4 (3)	C21—C22—H22	120.00
C20—C21—C22	122.3 (3)	C20—C23—H23B	109.00
C17—C22—C21	120.8 (3)	C20—C23—H23C	109.00
C1—C2—H2	122.00	C20—C23—H23A	110.00
C3—C2—H2	122.00	H23A—C23—H23C	109.00
C4—C3—H3	119.00	H23B—C23—H23C	109.00
C2—C3—H3	119.00	H23A—C23—H23B	109.00
C7—N1—C1—C2	178.9 (2)	C4—C5—C6—C1	−0.2 (3)
C16—N1—C1—C2	−5.1 (3)	N2—C8—C9—C14	87.7 (3)
C7—N1—C1—C6	0.3 (2)	N2—C8—C9—C10	−89.4 (3)
C16—N1—C1—C6	176.30 (19)	C8—C9—C14—C13	−175.1 (3)
C1—N1—C7—N2	0.1 (2)	C8—C9—C10—C11	174.1 (3)
C16—N1—C7—N2	−175.98 (19)	C14—C9—C10—C11	−3.1 (5)
C1—N1—C16—C17	−84.9 (3)	C10—C9—C14—C13	2.1 (5)
C7—N1—C16—C17	90.4 (3)	C9—C10—C11—C12	1.4 (6)
C6—N2—C8—C9	86.8 (3)	C10—C11—C12—C15	−178.9 (4)
C7—N2—C8—C9	−87.0 (3)	C10—C11—C12—C13	1.4 (5)
C7—N2—C6—C5	−179.0 (2)	C11—C12—C13—C14	−2.4 (5)
C8—N2—C6—C5	6.4 (3)	C15—C12—C13—C14	177.9 (4)
C7—N2—C6—C1	0.6 (2)	C12—C13—C14—C9	0.7 (5)
C8—N2—C6—C1	−174.04 (18)	N1—C16—C17—C18	112.9 (3)
C6—N2—C7—N1	−0.4 (2)	N1—C16—C17—C22	−66.2 (3)
C8—N2—C7—N1	174.33 (18)	C16—C17—C18—C19	−178.3 (3)
N1—C1—C2—C3	−179.1 (2)	C22—C17—C18—C19	0.9 (5)
C2—C1—C6—C5	0.4 (3)	C16—C17—C22—C21	178.3 (2)
N1—C1—C6—C5	179.15 (18)	C18—C17—C22—C21	−0.8 (4)
C6—C1—C2—C3	−0.7 (3)	C17—C18—C19—C20	−0.9 (5)
C2—C1—C6—N2	−179.25 (18)	C18—C19—C20—C21	0.8 (5)
N1—C1—C6—N2	−0.5 (2)	C18—C19—C20—C23	179.5 (3)
C1—C2—C3—C4	0.7 (3)	C19—C20—C21—C22	−0.7 (4)
C2—C3—C4—C5	−0.6 (4)	C23—C20—C21—C22	−179.4 (3)
C3—C4—C5—C6	0.2 (3)	C20—C21—C22—C17	0.8 (4)
C4—C5—C6—N2	179.4 (2)

Symmetry codes: (i) −x+1, −y, −z+1; (ii) x, y−1, z; (iii) −x, −y, −z+1; (iv) x, y, z−1; (v) −x, −y+1, −z+1; (vi) x, y, z+1; (vii) −x, −y+1, −z+2; (viii) −x+1, −y+1, −z+2; (ix) −x, −y, −z+2; (x) −x+1, −y, −z+2; (xi) x, y+1, z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H101···Cl1^i	1.02 (5)	2.41 (4)	3.189 (3)	132 (3)
O1—H102···Cl1	0.84 (5)	2.43 (5)	3.155 (3)	146 (4)
C7—H7···O1^i	0.93	2.32	3.227 (4)	164
C8—H8a···Cl1^xi	0.97	2.74	3.692 (3)	167
C8—H8b···Cl1^i	0.97	2.77	3.730 (3)	170
C16—H16a···Cl1	0.97	2.67	3.633 (3)	170

Symmetry codes: (i) −x+1, −y, −z+1; (xi) x, y+1, z.