1-Diphenyl-methyl-4-[3-(4-fluoro-benzo-yl)prop-yl]piperazine-1,4-diium dichloride monohydrate.

In the title compound, C(27)H(31)FN(2)O(2+)·2Cl(-)·H(2)O, the piperazine ring adopts a chair conformation and both N atoms are protonated. The Cl(-) anions form strong hydrogen bonds to these protons. O/N-H⋯Cl and C-H⋯O hydrogen bonds link the anions, cations and water of hydration into a three-dimensional network.

Related literature

For a related structure, see: Zhou & Jin (1986 ▶). For the synthesis of 1-diphenyl­methyl-4-[3-(4-fluoro­benzo­yl)prop­yl]piperazine, see: Wang et al. (2003 ▶).

Experimental

Crystal data

C27H31FN2O2+·2Cl−·H2O

M = 507.45

Monoclinic,

a = 39.2849 (14) Å

b = 7.3369 (3) Å

c = 19.5158 (7) Å

β = 107.773 (2)°

V = 5356.6 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.28 mm−1

T = 298 K

0.37 × 0.21 × 0.11 mm

Data collection

Siemens SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.933, T max = 0.970

19739 measured reflections

4566 independent reflections

3644 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.138

S = 1.03

4566 reflections

313 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.37 e Å−3

Data collection: SMART (Siemens, 1994 ▶); cell refinement: SAINT (Siemens, 1994 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablock(s) global. DOI: 10.1107/S1600536811037378/pv2438sup1.cif

Supplementary material file. DOI: 10.1107/S1600536811037378/pv2438globalsup2.cml

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

C27H31FN2O2+·2Cl−·H2O	F(000) = 2144
Mr = 507.45	Dx = 1.258 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -C 2yc	Cell parameters from 6877 reflections
a = 39.2849 (14) Å	θ = 4.6–65.2°
b = 7.3369 (3) Å	µ = 0.28 mm−1
c = 19.5158 (7) Å	T = 298 K
β = 107.773 (2)°	Prismatic, colorless
V = 5356.6 (3) Å3	0.37 × 0.21 × 0.11 mm
Z = 8

Siemens SMART CCD area-detector diffractometer	4566 independent reflections
Radiation source: fine-focus sealed tube	3644 reflections with I > 2σ(I)
graphite	Rint = 0.034
φ and ω scans	θmax = 24.9°, θmin = 1.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −46→44
Tmin = 0.933, Tmax = 0.970	k = −8→7
19739 measured reflections	l = −22→23

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.138	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.0742P)2 + 3.1528P] where P = (Fo2 + 2Fc2)/3
4566 reflections	(Δ/σ)max < 0.001
313 parameters	Δρmax = 0.31 e Å−3
3 restraints	Δρmin = −0.37 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
F1	0.40283 (5)	0.3181 (3)	0.13299 (11)	0.1153 (7)
Cl1	0.113600 (17)	0.81655 (8)	0.10513 (4)	0.0702 (2)
Cl2	0.231844 (18)	1.53814 (9)	0.16249 (4)	0.0760 (2)
N1	0.19895 (4)	1.1685 (2)	0.12880 (9)	0.0468 (4)
H1A	0.2087	1.2821	0.1339	0.056*
N2	0.12309 (4)	1.2321 (2)	0.10926 (8)	0.0441 (4)
H2B	0.1166	1.1127	0.1041	0.053*
O1	0.31404 (6)	1.0374 (3)	0.04357 (12)	0.0918 (7)
O1W	0.17734 (9)	1.6776 (4)	0.24451 (15)	0.1295 (9)
C1	0.37946 (8)	0.4599 (4)	0.11920 (14)	0.0765 (8)
C2	0.38710 (7)	0.6077 (5)	0.08508 (15)	0.0792 (8)
H2A	0.4078	0.6117	0.0714	0.095*
C3	0.36369 (7)	0.7509 (4)	0.07114 (13)	0.0674 (6)
H3A	0.3688	0.8540	0.0482	0.081*
C4	0.33248 (6)	0.7454 (3)	0.09058 (11)	0.0541 (5)
C5	0.32535 (7)	0.5884 (3)	0.12420 (12)	0.0643 (6)
H5A	0.3044	0.5807	0.1368	0.077*
C6	0.34905 (8)	0.4448 (4)	0.13884 (14)	0.0771 (8)
H6A	0.3445	0.3403	0.1615	0.092*
C7	0.30841 (6)	0.9070 (3)	0.07606 (12)	0.0572 (5)
C8	0.27859 (7)	0.9051 (4)	0.10829 (17)	0.0789 (8)
H8A	0.2890	0.9003	0.1602	0.095*
H8B	0.2652	0.7931	0.0936	0.095*
C9	0.25220 (6)	1.0625 (3)	0.09051 (14)	0.0641 (6)
H9A	0.2646	1.1783	0.1017	0.077*
H9B	0.2385	1.0613	0.0399	0.077*
C10	0.22818 (6)	1.0325 (3)	0.13699 (13)	0.0596 (6)
H10A	0.2175	0.9126	0.1263	0.072*
H10B	0.2429	1.0319	0.1869	0.072*
C11	0.18253 (5)	1.1380 (3)	0.18779 (11)	0.0537 (5)
H11A	0.2003	1.1619	0.2337	0.064*
H11B	0.1754	1.0113	0.1873	0.064*
C12	0.15059 (5)	1.2567 (3)	0.18091 (11)	0.0541 (5)
H12A	0.1402	1.2264	0.2187	0.065*
H12B	0.1580	1.3833	0.1868	0.065*
C13	0.14022 (5)	1.2799 (3)	0.05275 (11)	0.0502 (5)
H13A	0.1484	1.4053	0.0591	0.060*
H13B	0.1227	1.2691	0.0055	0.060*
C14	0.17127 (5)	1.1568 (3)	0.05701 (11)	0.0506 (5)
H14A	0.1629	1.0321	0.0482	0.061*
H14B	0.1818	1.1905	0.0199	0.061*
C15	0.08987 (5)	1.3469 (3)	0.10174 (11)	0.0491 (5)
H15A	0.0973	1.4748	0.1041	0.059*
C16	0.06201 (5)	1.3197 (3)	0.02871 (11)	0.0519 (5)
C17	0.04723 (6)	1.4723 (4)	−0.01065 (13)	0.0651 (6)
H17A	0.0555	1.5876	0.0063	0.078*
C18	0.02014 (7)	1.4545 (5)	−0.07510 (15)	0.0835 (9)
H18A	0.0100	1.5580	−0.1008	0.100*
C19	0.00813 (7)	1.2854 (5)	−0.10126 (14)	0.0836 (9)
H19A	−0.0099	1.2742	−0.1449	0.100*
C20	0.02270 (7)	1.1335 (4)	−0.06319 (14)	0.0786 (8)
H20A	0.0146	1.0187	−0.0810	0.094*
C21	0.04927 (6)	1.1494 (4)	0.00130 (13)	0.0667 (6)
H21A	0.0589	1.0450	0.0270	0.080*
C22	0.07512 (5)	1.3157 (3)	0.16414 (11)	0.0517 (5)
C23	0.06211 (7)	1.1488 (4)	0.17795 (13)	0.0659 (6)
H23A	0.0631	1.0490	0.1493	0.079*
C24	0.04770 (8)	1.1286 (5)	0.23378 (15)	0.0806 (8)
H24A	0.0392	1.0157	0.2427	0.097*
C25	0.04600 (8)	1.2757 (5)	0.27604 (15)	0.0833 (9)
H25A	0.0360	1.2629	0.3133	0.100*
C26	0.05902 (8)	1.4419 (5)	0.26328 (15)	0.0822 (8)
H26A	0.0579	1.5415	0.2920	0.099*
C27	0.07369 (6)	1.4609 (4)	0.20780 (13)	0.0645 (6)
H27A	0.0827	1.5733	0.1998	0.077*
H2	0.1952 (5)	1.647 (4)	0.2183 (13)	0.080*
H1	0.1574 (5)	1.726 (4)	0.2022 (12)	0.080*

	U11	U22	U33	U12	U13	U23
F1	0.1138 (14)	0.1047 (15)	0.1215 (14)	0.0581 (12)	0.0270 (12)	0.0098 (11)
Cl1	0.0742 (4)	0.0398 (4)	0.0921 (5)	−0.0111 (3)	0.0189 (3)	0.0043 (3)
Cl2	0.0754 (4)	0.0481 (4)	0.1010 (5)	−0.0194 (3)	0.0220 (3)	−0.0042 (3)
N1	0.0441 (9)	0.0382 (10)	0.0579 (9)	−0.0057 (7)	0.0152 (7)	0.0007 (7)
N2	0.0423 (8)	0.0386 (9)	0.0499 (9)	−0.0064 (7)	0.0121 (7)	0.0007 (7)
O1	0.1009 (14)	0.0751 (13)	0.1225 (16)	0.0187 (11)	0.0686 (13)	0.0393 (12)
O1W	0.144 (2)	0.123 (2)	0.125 (2)	0.0220 (19)	0.0457 (18)	0.0110 (17)
C1	0.0786 (17)	0.079 (2)	0.0646 (15)	0.0263 (15)	0.0118 (13)	−0.0046 (13)
C2	0.0598 (14)	0.098 (2)	0.0800 (17)	0.0155 (15)	0.0208 (13)	−0.0043 (16)
C3	0.0631 (14)	0.0712 (17)	0.0712 (15)	0.0020 (13)	0.0254 (12)	0.0036 (12)
C4	0.0599 (12)	0.0560 (14)	0.0480 (11)	0.0000 (10)	0.0188 (9)	−0.0041 (10)
C5	0.0777 (15)	0.0558 (15)	0.0665 (14)	0.0032 (12)	0.0326 (12)	−0.0030 (11)
C6	0.109 (2)	0.0569 (16)	0.0660 (15)	0.0144 (15)	0.0272 (15)	0.0042 (12)
C7	0.0627 (13)	0.0557 (14)	0.0581 (12)	−0.0010 (11)	0.0255 (10)	0.0012 (11)
C8	0.0805 (17)	0.0615 (17)	0.111 (2)	0.0126 (14)	0.0531 (16)	0.0169 (15)
C9	0.0617 (13)	0.0576 (15)	0.0790 (15)	0.0048 (11)	0.0304 (12)	0.0067 (12)
C10	0.0559 (12)	0.0500 (14)	0.0749 (14)	0.0084 (10)	0.0229 (11)	0.0085 (11)
C11	0.0470 (11)	0.0611 (14)	0.0518 (11)	−0.0029 (10)	0.0134 (9)	0.0033 (10)
C12	0.0461 (11)	0.0627 (14)	0.0508 (11)	−0.0054 (10)	0.0108 (9)	−0.0042 (10)
C13	0.0486 (11)	0.0508 (13)	0.0513 (11)	−0.0047 (9)	0.0155 (9)	0.0072 (9)
C14	0.0520 (11)	0.0502 (13)	0.0511 (11)	−0.0057 (9)	0.0179 (9)	0.0006 (9)
C15	0.0452 (11)	0.0420 (12)	0.0593 (12)	−0.0013 (9)	0.0150 (9)	0.0017 (9)
C16	0.0440 (11)	0.0548 (14)	0.0586 (12)	−0.0001 (9)	0.0182 (9)	0.0064 (10)
C17	0.0606 (13)	0.0635 (16)	0.0716 (15)	0.0045 (11)	0.0210 (11)	0.0164 (12)
C18	0.0712 (17)	0.103 (2)	0.0725 (17)	0.0185 (16)	0.0164 (14)	0.0345 (17)
C19	0.0618 (15)	0.116 (3)	0.0626 (15)	0.0045 (17)	0.0036 (12)	0.0000 (16)
C20	0.0600 (14)	0.087 (2)	0.0766 (16)	−0.0051 (14)	0.0030 (13)	−0.0089 (15)
C21	0.0544 (13)	0.0627 (16)	0.0728 (15)	−0.0016 (11)	0.0041 (11)	0.0014 (12)
C22	0.0399 (10)	0.0559 (14)	0.0568 (12)	0.0007 (9)	0.0109 (9)	0.0013 (10)
C23	0.0673 (14)	0.0645 (16)	0.0715 (15)	−0.0109 (12)	0.0296 (12)	−0.0033 (12)
C24	0.0774 (17)	0.090 (2)	0.0803 (17)	−0.0155 (15)	0.0334 (14)	0.0072 (16)
C25	0.0710 (17)	0.120 (3)	0.0631 (15)	−0.0051 (17)	0.0271 (13)	−0.0011 (16)
C26	0.0793 (18)	0.098 (2)	0.0704 (16)	0.0046 (17)	0.0243 (14)	−0.0194 (15)
C27	0.0610 (13)	0.0642 (16)	0.0665 (14)	−0.0005 (11)	0.0167 (11)	−0.0079 (12)

F1—C1	1.359 (3)	C11—H11B	0.9700
N1—C14	1.491 (3)	C12—H12A	0.9700
N1—C10	1.493 (3)	C12—H12B	0.9700
N1—C11	1.498 (3)	C13—C14	1.500 (3)
N1—H1A	0.9100	C13—H13A	0.9700
N2—C12	1.494 (3)	C13—H13B	0.9700
N2—C13	1.498 (2)	C14—H14A	0.9700
N2—C15	1.522 (3)	C14—H14B	0.9700
N2—H2B	0.9100	C15—C22	1.517 (3)
O1—C7	1.206 (3)	C15—C16	1.522 (3)
O1W—H2	1.012 (16)	C15—H15A	0.9800
O1W—H1	1.013 (16)	C16—C17	1.381 (3)
C1—C2	1.353 (4)	C16—C21	1.391 (3)
C1—C6	1.366 (4)	C17—C18	1.384 (4)
C2—C3	1.368 (4)	C17—H17A	0.9300
C2—H2A	0.9300	C18—C19	1.369 (4)
C3—C4	1.390 (3)	C18—H18A	0.9300
C3—H3A	0.9300	C19—C20	1.365 (4)
C4—C5	1.396 (3)	C19—H19A	0.9300
C4—C7	1.489 (3)	C20—C21	1.373 (3)
C5—C6	1.377 (4)	C20—H20A	0.9300
C5—H5A	0.9300	C21—H21A	0.9300
C6—H6A	0.9300	C22—C27	1.376 (3)
C7—C8	1.489 (3)	C22—C23	1.384 (3)
C8—C9	1.519 (4)	C23—C24	1.381 (4)
C8—H8A	0.9700	C23—H23A	0.9300
C8—H8B	0.9700	C24—C25	1.372 (4)
C9—C10	1.511 (3)	C24—H24A	0.9300
C9—H9A	0.9700	C25—C26	1.374 (4)
C9—H9B	0.9700	C25—H25A	0.9300
C10—H10A	0.9700	C26—C27	1.380 (4)
C10—H10B	0.9700	C26—H26A	0.9300
C11—C12	1.499 (3)	C27—H27A	0.9300
C11—H11A	0.9700
C14—N1—C10	112.26 (17)	N2—C12—H12A	109.4
C14—N1—C11	110.60 (15)	C11—C12—H12A	109.4
C10—N1—C11	108.40 (16)	N2—C12—H12B	109.4
C14—N1—H1A	108.5	C11—C12—H12B	109.4
C10—N1—H1A	108.5	H12A—C12—H12B	108.0
C11—N1—H1A	108.5	N2—C13—C14	111.04 (16)
C12—N2—C13	107.56 (15)	N2—C13—H13A	109.4
C12—N2—C15	112.16 (16)	C14—C13—H13A	109.4
C13—N2—C15	111.36 (15)	N2—C13—H13B	109.4
C12—N2—H2B	108.6	C14—C13—H13B	109.4
C13—N2—H2B	108.6	H13A—C13—H13B	108.0
C15—N2—H2B	108.6	N1—C14—C13	111.42 (17)
H2—O1W—H1	98.6 (16)	N1—C14—H14A	109.3
C2—C1—F1	118.2 (3)	C13—C14—H14A	109.3
C2—C1—C6	123.2 (3)	N1—C14—H14B	109.3
F1—C1—C6	118.6 (3)	C13—C14—H14B	109.3
C1—C2—C3	118.5 (3)	H14A—C14—H14B	108.0
C1—C2—H2A	120.8	C22—C15—C16	112.97 (16)
C3—C2—H2A	120.8	C22—C15—N2	111.43 (16)
C2—C3—C4	121.2 (3)	C16—C15—N2	111.58 (16)
C2—C3—H3A	119.4	C22—C15—H15A	106.8
C4—C3—H3A	119.4	C16—C15—H15A	106.8
C3—C4—C5	118.2 (2)	N2—C15—H15A	106.8
C3—C4—C7	119.1 (2)	C17—C16—C21	118.3 (2)
C5—C4—C7	122.6 (2)	C17—C16—C15	118.3 (2)
C6—C5—C4	120.6 (2)	C21—C16—C15	123.32 (19)
C6—C5—H5A	119.7	C16—C17—C18	120.3 (3)
C4—C5—H5A	119.7	C16—C17—H17A	119.8
C1—C6—C5	118.3 (3)	C18—C17—H17A	119.8
C1—C6—H6A	120.9	C19—C18—C17	120.4 (3)
C5—C6—H6A	120.9	C19—C18—H18A	119.8
O1—C7—C4	121.6 (2)	C17—C18—H18A	119.8
O1—C7—C8	121.6 (2)	C20—C19—C18	119.8 (2)
C4—C7—C8	116.6 (2)	C20—C19—H19A	120.1
C7—C8—C9	117.8 (2)	C18—C19—H19A	120.1
C7—C8—H8A	107.9	C19—C20—C21	120.3 (3)
C9—C8—H8A	107.9	C19—C20—H20A	119.8
C7—C8—H8B	107.9	C21—C20—H20A	119.8
C9—C8—H8B	107.9	C20—C21—C16	120.8 (2)
H8A—C8—H8B	107.2	C20—C21—H21A	119.6
C10—C9—C8	105.03 (19)	C16—C21—H21A	119.6
C10—C9—H9A	110.7	C27—C22—C23	118.5 (2)
C8—C9—H9A	110.7	C27—C22—C15	118.5 (2)
C10—C9—H9B	110.7	C23—C22—C15	123.0 (2)
C8—C9—H9B	110.7	C24—C23—C22	120.9 (3)
H9A—C9—H9B	108.8	C24—C23—H23A	119.6
N1—C10—C9	116.04 (19)	C22—C23—H23A	119.6
N1—C10—H10A	108.3	C25—C24—C23	119.8 (3)
C9—C10—H10A	108.3	C25—C24—H24A	120.1
N1—C10—H10B	108.3	C23—C24—H24A	120.1
C9—C10—H10B	108.3	C24—C25—C26	120.0 (3)
H10A—C10—H10B	107.4	C24—C25—H25A	120.0
N1—C11—C12	112.92 (17)	C26—C25—H25A	120.0
N1—C11—H11A	109.0	C25—C26—C27	120.0 (3)
C12—C11—H11A	109.0	C25—C26—H26A	120.0
N1—C11—H11B	109.0	C27—C26—H26A	120.0
C12—C11—H11B	109.0	C22—C27—C26	120.9 (3)
H11A—C11—H11B	107.8	C22—C27—H27A	119.6
N2—C12—C11	111.11 (17)	C26—C27—H27A	119.6
F1—C1—C2—C3	−179.9 (2)	N2—C13—C14—N1	−59.1 (2)
C6—C1—C2—C3	1.7 (4)	C12—N2—C15—C22	−52.4 (2)
C1—C2—C3—C4	−0.8 (4)	C13—N2—C15—C22	−172.96 (17)
C2—C3—C4—C5	−0.7 (4)	C12—N2—C15—C16	−179.67 (17)
C2—C3—C4—C7	178.3 (2)	C13—N2—C15—C16	59.7 (2)
C3—C4—C5—C6	1.3 (3)	C22—C15—C16—C17	103.2 (2)
C7—C4—C5—C6	−177.7 (2)	N2—C15—C16—C17	−130.3 (2)
C2—C1—C6—C5	−1.1 (4)	C22—C15—C16—C21	−73.2 (3)
F1—C1—C6—C5	−179.5 (2)	N2—C15—C16—C21	53.3 (3)
C4—C5—C6—C1	−0.4 (4)	C21—C16—C17—C18	0.9 (3)
C3—C4—C7—O1	5.1 (4)	C15—C16—C17—C18	−175.7 (2)
C5—C4—C7—O1	−176.0 (2)	C16—C17—C18—C19	−1.2 (4)
C3—C4—C7—C8	−170.5 (2)	C17—C18—C19—C20	0.7 (5)
C5—C4—C7—C8	8.4 (3)	C18—C19—C20—C21	0.2 (5)
O1—C7—C8—C9	8.1 (4)	C19—C20—C21—C16	−0.5 (4)
C4—C7—C8—C9	−176.2 (2)	C17—C16—C21—C20	0.0 (4)
C7—C8—C9—C10	−173.9 (2)	C15—C16—C21—C20	176.4 (2)
C14—N1—C10—C9	68.0 (3)	C16—C15—C22—C27	−115.0 (2)
C11—N1—C10—C9	−169.6 (2)	N2—C15—C22—C27	118.5 (2)
C8—C9—C10—N1	−178.9 (2)	C16—C15—C22—C23	63.2 (3)
C14—N1—C11—C12	−51.4 (2)	N2—C15—C22—C23	−63.4 (3)
C10—N1—C11—C12	−174.83 (18)	C27—C22—C23—C24	0.6 (4)
C13—N2—C12—C11	−59.0 (2)	C15—C22—C23—C24	−177.5 (2)
C15—N2—C12—C11	178.27 (17)	C22—C23—C24—C25	0.4 (4)
N1—C11—C12—N2	55.8 (2)	C23—C24—C25—C26	−0.8 (4)
C12—N2—C13—C14	61.0 (2)	C24—C25—C26—C27	0.2 (4)
C15—N2—C13—C14	−175.72 (16)	C23—C22—C27—C26	−1.2 (4)
C10—N1—C14—C13	173.75 (17)	C15—C22—C27—C26	177.0 (2)
C11—N1—C14—C13	52.5 (2)	C25—C26—C27—C22	0.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1···Cl1i	1.01 (2)	2.24 (2)	3.248 (3)	176 (2)
C15—H15A···Cl1i	0.98	2.59	3.565 (2)	177
C6—H6A···O1Wii	0.93	2.55	3.397 (4)	152
C10—H10B···Cl2iii	0.97	2.80	3.746 (3)	165
C14—H14B···O1iv	0.97	2.38	3.148 (3)	136
N1—H1A···Cl2	0.91	2.09	2.990 (2)	171
O1W—H2···Cl2	1.01 (2)	2.20 (2)	3.207 (3)	172 (2)
N2—H2B···Cl1	0.91	2.18	3.070 (2)	167
C12—H12B···O1W	0.97	2.45	3.374 (4)	160
C21—H21A···Cl1	0.93	2.78	3.651 (3)	155

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1⋯Cl1i	1.01 (2)	2.24 (2)	3.248 (3)	176 (2)
C6—H6A⋯O1Wii	0.93	2.55	3.397 (4)	152
C14—H14B⋯O1iii	0.97	2.38	3.148 (3)	136
N1—H1A⋯Cl2	0.91	2.09	2.990 (2)	171
O1W—H2⋯Cl2	1.01 (2)	2.20 (2)	3.207 (3)	172 (2)
N2—H2B⋯Cl1	0.91	2.18	3.070 (2)	167

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