2-(Furan-2-yl)-1,3-bis(furan-2-ylmeth-yl)-1H-benzimidazol-3-ium chloride monohydrate.

The title hydrated salt, C(21)H(17)N(2)O(3) (+)·Cl(-)·H(2)O, exhibits disorder in one of the furan rings. The major and minor components have a refined occupancy ratio of 0.844 (19):0.156 (19). The structure displays intermolecular hydrogen bonding involving the water molecule and the chloride anion. Close intermolecular C-H⋯Cl and C-H⋯(furan ring) inter-actions complete the hydrogen bonding.

Related literature

For examples of the synthesis of substituted benzimidazolium salts, see: Wang & Chang (2006 ▶); Hoesl et al. (2004 ▶); Rivas et al. (2001 ▶, 2002 ▶). For examples of structures of other tris­ubstituted benzimidazolium salts, see: Ennajih et al. (2009 ▶, 2010 ▶); Akkurt et al. (2008 ▶, 2004 ▶); Smith & Luss (1975 ▶). For the structure of 1,3-bis(furan-2-ylmethyl)-1H-benzo[d]imidazol-3-ium chloride, see: Akkurt et al. (2009 ▶). For other related literature, see: Costache et al. (2007 ▶); Elmali et al. (2005 ▶); Hayakawa et al. (1996 ▶); Horton et al. (2003 ▶); Nahlé et al. (2012 ▶); Welton (1999 ▶).

Experimental

Crystal data

C21H17N2O3 +·Cl−·H2O

M = 398.83

Triclinic,

a = 9.4723 (12) Å

b = 9.9129 (14) Å

c = 11.2779 (16) Å

α = 97.980 (5)°

β = 110.359 (4)°

γ = 93.547 (4)°

V = 976.3 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.23 mm−1

T = 200 K

0.30 × 0.07 × 0.07 mm

Data collection

Bruker SMART X2S benchtop diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.91, T max = 0.98

9477 measured reflections

3419 independent reflections

2732 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.129

S = 1.05

3419 reflections

272 parameters

10 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.62 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: XSHELL (Bruker, 2004 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812040135/gg2097sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812040135/gg2097Isup3.hkl

Supplementary material file. DOI: 10.1107/S1600536812040135/gg2097Isup4.mol

Supplementary material file. DOI: 10.1107/S1600536812040135/gg2097Isup4.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H17N2O3+·Cl−·H2O	Z = 2
Mr = 398.83	F(000) = 416
Triclinic, P1	Dx = 1.357 Mg m−3
a = 9.4723 (12) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.9129 (14) Å	Cell parameters from 3551 reflections
c = 11.2779 (16) Å	θ = 2.4–24.8°
α = 97.980 (5)°	µ = 0.23 mm−1
β = 110.359 (4)°	T = 200 K
γ = 93.547 (4)°	Needle, clear colourless
V = 976.3 (2) Å3	0.30 × 0.07 × 0.07 mm

Bruker SMART X2S benchtop diffractometer	3419 independent reflections
Radiation source: XOS X-beam microfocus source, Bruker SMART X2S benchtop	2732 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromator	Rint = 0.036
Detector resolution: 8.3330 pixels mm-1	θmax = 25.2°, θmin = 2.0°
ω scans	h = −11→11
Absorption correction: multi-scan (SADABS; Bruker, 2009)	k = −11→11
Tmin = 0.91, Tmax = 0.98	l = −13→13
9477 measured reflections

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ2(Fo2) + (0.0633P)2 + 0.4042P] where P = (Fo2 + 2Fc2)/3
3419 reflections	(Δ/σ)max < 0.001
272 parameters	Δρmax = 0.62 e Å−3
10 restraints	Δρmin = −0.21 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) 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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
Cl1	0.44526 (6)	0.74517 (6)	0.50520 (6)	0.0460 (2)
OW	0.6147 (4)	0.9554 (2)	0.3947 (2)	0.0967 (9)
HO1	0.597 (5)	1.033 (2)	0.423 (4)	0.145*
HO2	0.575 (5)	0.902 (3)	0.429 (4)	0.145*
C1	0.1566 (2)	0.5684 (2)	0.68521 (18)	0.0318 (5)
C2	0.0112 (2)	0.5062 (2)	0.66052 (18)	0.0311 (5)
C3	−0.0290 (3)	0.3649 (2)	0.62089 (19)	0.0365 (5)
H3	−0.1283	0.3225	0.6042	0.044*
C4	0.0851 (3)	0.2905 (2)	0.6075 (2)	0.0435 (6)
H4	0.0638	0.1938	0.5817	0.052*
C5	0.2319 (3)	0.3538 (3)	0.6310 (2)	0.0449 (6)
H5	0.3062	0.2986	0.6197	0.054*
C6	0.2706 (3)	0.4929 (2)	0.6698 (2)	0.0398 (5)
H6	0.3695	0.5354	0.6853	0.048*
N1	−0.07374 (18)	0.61074 (18)	0.68249 (15)	0.0303 (4)
C7	0.0161 (2)	0.7312 (2)	0.72021 (18)	0.0312 (5)
N2	0.15618 (19)	0.70877 (18)	0.72206 (15)	0.0316 (4)
C8	−0.0297 (2)	0.8639 (2)	0.7526 (2)	0.0371 (5)
C9	0.0340 (8)	0.9713 (6)	0.8502 (5)	0.0481 (14)	0.844 (19)
H9	0.1283	0.9784	0.9192	0.058*	0.844 (19)
C10	−0.0713 (7)	1.0725 (7)	0.8273 (7)	0.0587 (14)	0.844 (19)
H10	−0.0589	1.16	0.8787	0.07*	0.844 (19)
C11	−0.1853 (5)	1.0220 (6)	0.7243 (8)	0.0689 (16)	0.844 (19)
H11	−0.2715	1.0677	0.6884	0.083*	0.844 (19)
O1	−0.1656 (4)	0.8939 (6)	0.6734 (6)	0.0664 (14)	0.844 (19)
C9'	0.059 (5)	0.970 (3)	0.843 (3)	0.0481 (14)	0.156 (19)
H9'	0.1661	0.9845	0.887	0.058*	0.156 (19)
C10'	−0.057 (4)	1.053 (5)	0.850 (4)	0.0587 (14)	0.156 (19)
H10'	−0.0414	1.1381	0.9055	0.07*	0.156 (19)
C11'	−0.187 (3)	0.992 (3)	0.770 (3)	0.0689 (16)	0.156 (19)
H11'	−0.2783	1.0324	0.7541	0.083*	0.156 (19)
O1'	−0.1809 (18)	0.862 (2)	0.708 (3)	0.0664 (14)	0.156 (19)
C12	−0.2298 (2)	0.5859 (2)	0.6823 (2)	0.0389 (5)
H12A	−0.29	0.5136	0.6089	0.047*
H12B	−0.2793	0.6709	0.6721	0.047*
C13	−0.2264 (2)	0.5425 (2)	0.8045 (2)	0.0378 (5)
C14	−0.2923 (3)	0.4323 (3)	0.8311 (2)	0.0524 (7)
H14	−0.3555	0.3564	0.7712	0.063*
C15	−0.2481 (4)	0.4523 (3)	0.9676 (3)	0.0634 (8)
H15	−0.278	0.393	1.0161	0.076*
C16	−0.1564 (3)	0.5706 (3)	1.0140 (2)	0.0570 (7)
H16	−0.1082	0.6076	1.1027	0.068*
O2	−0.14159 (19)	0.63101 (18)	0.91660 (15)	0.0492 (4)
C17	0.2888 (2)	0.8126 (2)	0.7527 (2)	0.0387 (5)
H17A	0.2543	0.9046	0.7483	0.046*
H17B	0.337	0.7931	0.6881	0.046*
C18	0.4023 (3)	0.8125 (2)	0.8827 (2)	0.0424 (6)
C19	0.5399 (3)	0.7716 (3)	0.9248 (3)	0.0663 (8)
H19	0.5931	0.7321	0.8738	0.08*
C20	0.5922 (4)	0.7991 (4)	1.0628 (3)	0.0774 (10)
H20	0.6864	0.7807	1.1206	0.093*
C21	0.4837 (4)	0.8549 (3)	1.0937 (3)	0.0652 (8)
H21	0.4882	0.884	1.1789	0.078*
O3	0.3639 (2)	0.86463 (18)	0.98518 (16)	0.0523 (5)

	U11	U22	U33	U12	U13	U23
Cl1	0.0399 (4)	0.0385 (3)	0.0571 (4)	0.0009 (2)	0.0175 (3)	0.0011 (3)
OW	0.197 (3)	0.0528 (13)	0.0828 (16)	0.0360 (17)	0.0950 (18)	0.0222 (12)
C1	0.0345 (12)	0.0383 (12)	0.0231 (10)	0.0040 (9)	0.0104 (9)	0.0074 (8)
C2	0.0344 (12)	0.0379 (12)	0.0215 (9)	0.0063 (9)	0.0091 (8)	0.0084 (8)
C3	0.0400 (13)	0.0381 (12)	0.0290 (11)	0.0011 (10)	0.0095 (9)	0.0075 (9)
C4	0.0601 (16)	0.0352 (12)	0.0345 (12)	0.0095 (11)	0.0155 (11)	0.0055 (10)
C5	0.0477 (15)	0.0508 (15)	0.0397 (13)	0.0198 (12)	0.0173 (11)	0.0086 (11)
C6	0.0360 (12)	0.0494 (14)	0.0363 (12)	0.0098 (11)	0.0145 (10)	0.0086 (10)
N1	0.0274 (9)	0.0353 (10)	0.0271 (9)	0.0025 (8)	0.0082 (7)	0.0067 (7)
C7	0.0326 (11)	0.0373 (12)	0.0233 (10)	0.0021 (9)	0.0091 (8)	0.0075 (8)
N2	0.0295 (10)	0.0366 (10)	0.0290 (9)	0.0019 (8)	0.0110 (7)	0.0067 (7)
C8	0.0356 (12)	0.0401 (13)	0.0367 (12)	0.0067 (10)	0.0136 (10)	0.0080 (10)
C9	0.041 (3)	0.0451 (15)	0.0502 (16)	−0.0033 (18)	0.0118 (16)	−0.0023 (12)
C10	0.075 (3)	0.033 (3)	0.071 (3)	0.0086 (18)	0.032 (2)	0.002 (2)
C11	0.072 (2)	0.055 (2)	0.078 (4)	0.037 (2)	0.020 (2)	0.012 (2)
O1	0.0532 (14)	0.059 (2)	0.067 (2)	0.0210 (14)	−0.0006 (13)	−0.0014 (16)
C9'	0.041 (3)	0.0451 (15)	0.0502 (16)	−0.0033 (18)	0.0118 (16)	−0.0023 (12)
C10'	0.075 (3)	0.033 (3)	0.071 (3)	0.0086 (18)	0.032 (2)	0.002 (2)
C11'	0.072 (2)	0.055 (2)	0.078 (4)	0.037 (2)	0.020 (2)	0.012 (2)
O1'	0.0532 (14)	0.059 (2)	0.067 (2)	0.0210 (14)	−0.0006 (13)	−0.0014 (16)
C12	0.0333 (12)	0.0452 (13)	0.0379 (12)	0.0045 (10)	0.0119 (10)	0.0084 (10)
C13	0.0338 (12)	0.0430 (13)	0.0342 (12)	0.0038 (10)	0.0101 (9)	0.0043 (10)
C14	0.0618 (17)	0.0512 (16)	0.0424 (14)	−0.0091 (13)	0.0191 (12)	0.0079 (12)
C15	0.083 (2)	0.0618 (18)	0.0477 (15)	−0.0101 (16)	0.0261 (15)	0.0175 (14)
C16	0.0727 (19)	0.0634 (18)	0.0328 (13)	0.0045 (15)	0.0153 (12)	0.0126 (12)
O2	0.0529 (11)	0.0516 (10)	0.0393 (9)	−0.0029 (8)	0.0134 (8)	0.0083 (8)
C17	0.0362 (13)	0.0388 (13)	0.0432 (12)	−0.0026 (10)	0.0176 (10)	0.0089 (10)
C18	0.0373 (13)	0.0388 (13)	0.0461 (13)	−0.0051 (10)	0.0116 (11)	0.0044 (10)
C19	0.0443 (16)	0.072 (2)	0.071 (2)	0.0068 (14)	0.0087 (14)	0.0062 (16)
C20	0.0531 (19)	0.074 (2)	0.075 (2)	−0.0040 (17)	−0.0146 (16)	0.0171 (17)
C21	0.070 (2)	0.0564 (18)	0.0466 (16)	−0.0170 (16)	−0.0038 (14)	0.0111 (13)
O3	0.0532 (11)	0.0541 (11)	0.0432 (10)	−0.0020 (9)	0.0109 (8)	0.0085 (8)

OW—HO1	0.844 (10)	C9'—C10'	1.432 (18)
OW—HO2	0.847 (10)	C9'—H9'	0.95
C1—C2	1.391 (3)	C10'—C11'	1.297 (19)
C1—N2	1.397 (3)	C10'—H10'	0.95
C1—C6	1.397 (3)	C11'—O1'	1.388 (17)
C2—C3	1.395 (3)	C11'—H11'	0.95
C2—N1	1.398 (3)	C12—C13	1.489 (3)
C3—C4	1.384 (3)	C12—H12A	0.99
C3—H3	0.95	C12—H12B	0.99
C4—C5	1.410 (4)	C13—C14	1.345 (3)
C4—H4	0.95	C13—O2	1.383 (3)
C5—C6	1.373 (3)	C14—C15	1.429 (4)
C5—H5	0.95	C14—H14	0.95
C6—H6	0.95	C15—C16	1.338 (4)
N1—C7	1.347 (3)	C15—H15	0.95
N1—C12	1.483 (3)	C16—O2	1.365 (3)
C7—N2	1.352 (3)	C16—H16	0.95
C7—C8	1.449 (3)	C17—C18	1.486 (3)
N2—C17	1.482 (3)	C17—H17A	0.99
C8—O1'	1.341 (15)	C17—H17B	0.99
C8—C9	1.357 (4)	C18—C19	1.333 (4)
C8—C9'	1.358 (18)	C18—O3	1.373 (3)
C8—O1	1.366 (4)	C19—C20	1.439 (5)
C9—C10	1.444 (5)	C19—H19	0.95
C9—H9	0.95	C20—C21	1.322 (5)
C10—C11	1.290 (5)	C20—H20	0.95
C10—H10	0.95	C21—O3	1.369 (3)
C11—O1	1.371 (4)	C21—H21	0.95
C11—H11	0.95
HO1—OW—HO2	103 (2)	C8—C9'—H9'	130.8
C2—C1—N2	106.81 (18)	C10'—C9'—H9'	130.8
C2—C1—C6	121.7 (2)	C11'—C10'—C9'	109 (4)
N2—C1—C6	131.4 (2)	C11'—C10'—H10'	125.5
C1—C2—C3	122.2 (2)	C9'—C10'—H10'	125.5
C1—C2—N1	106.73 (18)	C10'—C11'—O1'	114 (3)
C3—C2—N1	131.0 (2)	C10'—C11'—H11'	122.8
C4—C3—C2	115.7 (2)	O1'—C11'—H11'	122.8
C4—C3—H3	122.1	C8—O1'—C11'	97.6 (17)
C2—C3—H3	122.1	N1—C12—C13	110.44 (17)
C3—C4—C5	122.0 (2)	N1—C12—H12A	109.6
C3—C4—H4	119.0	C13—C12—H12A	109.6
C5—C4—H4	119.0	N1—C12—H12B	109.6
C6—C5—C4	122.0 (2)	C13—C12—H12B	109.6
C6—C5—H5	119.0	H12A—C12—H12B	108.1
C4—C5—H5	119.0	C14—C13—O2	110.3 (2)
C5—C6—C1	116.3 (2)	C14—C13—C12	133.2 (2)
C5—C6—H6	121.8	O2—C13—C12	116.5 (2)
C1—C6—H6	121.8	C13—C14—C15	106.2 (2)
C7—N1—C2	108.79 (17)	C13—C14—H14	126.9
C7—N1—C12	126.83 (18)	C15—C14—H14	126.9
C2—N1—C12	123.78 (18)	C16—C15—C14	106.9 (2)
N1—C7—N2	109.02 (18)	C16—C15—H15	126.6
N1—C7—C8	125.66 (19)	C14—C15—H15	126.6
N2—C7—C8	125.32 (19)	C15—C16—O2	110.8 (2)
C7—N2—C1	108.65 (17)	C15—C16—H16	124.6
C7—N2—C17	127.40 (18)	O2—C16—H16	124.6
C1—N2—C17	123.92 (18)	C16—O2—C13	105.8 (2)
O1'—C8—C9	109.7 (10)	N2—C17—C18	111.56 (18)
O1'—C8—C9'	120 (2)	N2—C17—H17A	109.3
C9—C8—O1	109.0 (4)	C18—C17—H17A	109.3
C9'—C8—O1	116 (2)	N2—C17—H17B	109.3
O1'—C8—C7	112.0 (9)	C18—C17—H17B	109.3
C9—C8—C7	133.6 (4)	H17A—C17—H17B	108.0
C9'—C8—C7	126 (2)	C19—C18—O3	109.8 (2)
O1—C8—C7	117.5 (2)	C19—C18—C17	133.6 (3)
C8—C9—C10	105.8 (5)	O3—C18—C17	116.7 (2)
C8—C9—H9	127.1	C18—C19—C20	106.6 (3)
C10—C9—H9	127.1	C18—C19—H19	126.7
C11—C10—C9	107.3 (6)	C20—C19—H19	126.7
C11—C10—H10	126.3	C21—C20—C19	106.7 (3)
C9—C10—H10	126.3	C21—C20—H20	126.6
C10—C11—O1	111.1 (5)	C19—C20—H20	126.6
C10—C11—H11	124.5	C20—C21—O3	110.3 (3)
O1—C11—H11	124.4	C20—C21—H21	124.9
C8—O1—C11	106.8 (3)	O3—C21—H21	124.9
C8—C9'—C10'	98 (3)	C21—O3—C18	106.7 (2)
N2—C1—C2—C3	179.89 (18)	C9—C10—C11—O1	−0.7 (6)
C6—C1—C2—C3	1.0 (3)	O1'—C8—O1—C11	96 (2)
N2—C1—C2—N1	0.3 (2)	C9—C8—O1—C11	−0.3 (4)
C6—C1—C2—N1	−178.61 (18)	C9'—C8—O1—C11	−11 (2)
C1—C2—C3—C4	−0.1 (3)	C7—C8—O1—C11	178.9 (3)
N1—C2—C3—C4	179.42 (19)	C10—C11—O1—C8	0.6 (5)
C2—C3—C4—C5	−0.7 (3)	O1'—C8—C9'—C10'	−4 (2)
C3—C4—C5—C6	0.7 (3)	C9—C8—C9'—C10'	−33 (9)
C4—C5—C6—C1	0.2 (3)	O1—C8—C9'—C10'	24 (2)
C2—C1—C6—C5	−1.0 (3)	C7—C8—C9'—C10'	−166.6 (15)
N2—C1—C6—C5	−179.6 (2)	C8—C9'—C10'—C11'	−1 (2)
C1—C2—N1—C7	−0.6 (2)	C9'—C10'—C11'—O1'	5 (3)
C3—C2—N1—C7	179.8 (2)	C9—C8—O1'—C11'	12.4 (16)
C1—C2—N1—C12	−172.23 (17)	C9'—C8—O1'—C11'	6 (2)
C3—C2—N1—C12	8.2 (3)	O1—C8—O1'—C11'	−80 (2)
C2—N1—C7—N2	0.7 (2)	C7—C8—O1'—C11'	171.4 (13)
C12—N1—C7—N2	172.00 (17)	C10'—C11'—O1'—C8	−7 (3)
C2—N1—C7—C8	−179.78 (18)	C7—N1—C12—C13	−92.9 (2)
C12—N1—C7—C8	−8.5 (3)	C2—N1—C12—C13	77.2 (2)
N1—C7—N2—C1	−0.5 (2)	N1—C12—C13—C14	−124.4 (3)
C8—C7—N2—C1	179.96 (18)	N1—C12—C13—O2	57.0 (3)
N1—C7—N2—C17	177.42 (17)	O2—C13—C14—C15	0.5 (3)
C8—C7—N2—C17	−2.1 (3)	C12—C13—C14—C15	−178.2 (3)
C2—C1—N2—C7	0.1 (2)	C13—C14—C15—C16	−1.4 (3)
C6—C1—N2—C7	178.9 (2)	C14—C15—C16—O2	1.8 (4)
C2—C1—N2—C17	−177.90 (17)	C15—C16—O2—C13	−1.5 (3)
C6—C1—N2—C17	0.9 (3)	C14—C13—O2—C16	0.6 (3)
N1—C7—C8—O1'	−17.5 (16)	C12—C13—O2—C16	179.5 (2)
N2—C7—C8—O1'	161.9 (15)	C7—N2—C17—C18	105.0 (2)
N1—C7—C8—C9	134.8 (4)	C1—N2—C17—C18	−77.4 (2)
N2—C7—C8—C9	−45.8 (5)	N2—C17—C18—C19	108.4 (3)
N1—C7—C8—C9'	147 (2)	N2—C17—C18—O3	−71.7 (3)
N2—C7—C8—C9'	−34 (2)	O3—C18—C19—C20	0.2 (3)
N1—C7—C8—O1	−44.2 (5)	C17—C18—C19—C20	−180.0 (3)
N2—C7—C8—O1	135.2 (5)	C18—C19—C20—C21	−0.4 (4)
O1'—C8—C9—C10	−26.4 (14)	C19—C20—C21—O3	0.4 (4)
C9'—C8—C9—C10	127 (10)	C20—C21—O3—C18	−0.3 (3)
O1—C8—C9—C10	−0.1 (4)	C19—C18—O3—C21	0.1 (3)
C7—C8—C9—C10	−179.1 (4)	C17—C18—O3—C21	−179.8 (2)
C8—C9—C10—C11	0.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
OW—HO2···Cl1	0.85 (1)	2.35 (1)	3.189 (2)	174 (5)
OW—HO1···Cl1i	0.84 (1)	2.34 (1)	3.183 (2)	176 (4)
C9—H9···O3	0.95	2.49	3.278 (7)	141
C12—H12A···Cl1ii	0.99	2.77	3.694 (2)	155
C12—H12B···O1	0.99	2.39	3.098 (6)	127
C17—H17B···Cl1	0.99	2.61	3.594 (2)	176
C21—H21···OWiii	0.95	2.29	3.168 (4)	153
C15—H15···O3iv	0.95	2.62	3.436 (3)	143
C15—H15···C18iv	0.95	2.85	3.788 (4)	170
C15—H15···C21iv	0.95	2.87	3.498 (4)	124

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
OW—HO2⋯Cl1	0.85 (1)	2.35 (1)	3.189 (2)	174 (5)
OW—HO1⋯Cl1i	0.84 (1)	2.34 (1)	3.183 (2)	176 (4)
C9—H9⋯O3	0.95	2.49	3.278 (7)	141
C12—H12A⋯Cl1ii	0.99	2.77	3.694 (2)	155
C12—H12B⋯O1	0.99	2.39	3.098 (6)	127
C17—H17B⋯Cl1	0.99	2.61	3.594 (2)	176
C21—H21⋯OW iii	0.95	2.29	3.168 (4)	153
C15—H15⋯O3iv	0.95	2.62	3.436 (3)	143
C15—H15⋯C18iv	0.95	2.85	3.788 (4)	170
C15—H15⋯C21iv	0.95	2.87	3.498 (4)	124

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .