1-(2-Hy-droxy-eth-yl)-4-[3-(2-trifluoro-methyl-9H-thioxanthen-9-yl-idene)prop-yl]piperazine-1,4-diium dichloride: the dihydro-chloride salt of flupentixol.

In the title compound, C(23)H(27)F(3)N(2)OS(+)·2Cl(-), the piperazinediium ring adopts a chair conformation. The dihedral angle between the two outer aromatic rings of the 9H-thioxanthene unit is 40.35 (18)°. The F atoms in the trifluoro-methyl group are disordered over two sets of sites with occupancies of 0.803 (6) and 0.197 (6). In the crystal, mol-ecules are connected by N-H⋯Cl, O-H⋯Cl C-H⋯O and C-H⋯Cl hydrogen bonds, forming chains propagating along [001]. There are also C-H⋯π inter-actions present in the crystal structure.

Related literature

For the anti­depressant action of flupentixol, see: Robertson & Trimble (1981 ▶). For related structures, see: Post et al. (1975a ▶,b ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C23H27F3N2OS2+·2Cl−

M = 507.44

Monoclinic,

a = 34.1750 (17) Å

b = 7.1613 (3) Å

c = 22.6351 (11) Å

β = 115.307 (6)°

V = 5008.0 (5) Å3

Z = 8

Cu Kα radiation

μ = 3.46 mm−1

T = 295 K

0.43 × 0.34 × 0.21 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007 ▶) T min = 0.430, T max = 1.000

9840 measured reflections

5032 independent reflections

3792 reflections with I > 2σ(I)

R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.230

S = 1.05

5032 reflections

289 parameters

48 restraints

H-atom parameters constrained

Δρmax = 1.02 e Å−3

Δρmin = −0.43 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2007 ▶); 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: PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811028182/su2290sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811028182/su2290Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811028182/su2290Isup3.cml

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

C23H27F3N2OS2+·2Cl−	F(000) = 2112
Mr = 507.44	Dx = 1.346 Mg m−3
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -C 2yc	Cell parameters from 3191 reflections
a = 34.1750 (17) Å	θ = 5.2–75.3°
b = 7.1613 (3) Å	µ = 3.46 mm−1
c = 22.6351 (11) Å	T = 295 K
β = 115.307 (6)°	Prism, colourless
V = 5008.0 (5) Å3	0.43 × 0.34 × 0.21 mm
Z = 8

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	5032 independent reflections
Radiation source: Enhance (Cu) X-ray Source	3792 reflections with I > 2σ(I)
graphite	Rint = 0.028
Detector resolution: 10.5081 pixels mm-1	θmax = 75.4°, θmin = 5.5°
ω scans	h = −42→41
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	k = −8→8
Tmin = 0.430, Tmax = 1.000	l = −28→17
9840 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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.230	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.1341P)2 + 2.8648P] where P = (Fo2 + 2Fc2)/3
5032 reflections	(Δ/σ)max < 0.001
289 parameters	Δρmax = 1.02 e Å−3
48 restraints	Δρmin = −0.43 e Å−3

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.

	x	y	z	Uiso*/Ueq	Occ. (<1)
S	0.57461 (4)	1.14222 (16)	0.35221 (7)	0.0884 (4)
F1B	0.57123 (16)	0.4027 (6)	0.17114 (19)	0.1148 (16)	0.803 (6)
F2B	0.5404 (2)	0.6060 (7)	0.0960 (2)	0.153 (2)	0.803 (6)
F3B	0.50494 (14)	0.4598 (8)	0.1387 (3)	0.156 (2)	0.803 (6)
O1	0.81039 (14)	0.4005 (6)	0.22005 (15)	0.1096 (15)
N1	0.74387 (7)	0.4815 (4)	0.39823 (12)	0.0526 (7)
N2	0.81206 (8)	0.4717 (4)	0.35317 (11)	0.0554 (8)
C1	0.60586 (9)	0.7385 (5)	0.38628 (16)	0.0576 (9)
C2	0.58158 (6)	0.7828 (3)	0.31479 (8)	0.0575 (9)
C3	0.57390 (7)	0.6452 (2)	0.26781 (10)	0.0638 (10)
C4	0.55139 (7)	0.6884 (3)	0.20190 (9)	0.0691 (11)
C5	0.53658 (8)	0.8693 (4)	0.18297 (8)	0.0803 (14)
C6	0.54426 (8)	1.0069 (3)	0.22994 (12)	0.0813 (16)
C7	0.56677 (7)	0.9636 (3)	0.29585 (11)	0.0675 (11)
C8	0.57315 (10)	1.0114 (6)	0.41747 (19)	0.0704 (11)
C9	0.55696 (12)	1.0993 (8)	0.4577 (2)	0.0892 (18)
C10	0.55546 (13)	1.0009 (10)	0.5087 (2)	0.098 (2)
C11	0.56923 (16)	0.8215 (10)	0.5202 (2)	0.098 (2)
C12	0.58549 (13)	0.7320 (7)	0.48050 (19)	0.0804 (14)
C13	0.58772 (10)	0.8272 (6)	0.42855 (17)	0.0639 (10)
C14	0.54294 (13)	0.5409 (7)	0.15137 (18)	0.0959 (18)
C15	0.64145 (11)	0.6333 (5)	0.41210 (17)	0.0631 (10)
C16	0.66663 (10)	0.5476 (5)	0.37845 (17)	0.0623 (10)
C17	0.71416 (10)	0.5881 (5)	0.41901 (15)	0.0574 (9)
C18	0.78999 (10)	0.5299 (6)	0.44121 (14)	0.0654 (12)
C19	0.82119 (10)	0.4273 (6)	0.42243 (15)	0.0669 (12)
C20	0.76719 (10)	0.4095 (5)	0.31076 (15)	0.0609 (10)
C21	0.73502 (9)	0.5109 (5)	0.32828 (14)	0.0585 (9)
C22	0.84554 (11)	0.3868 (6)	0.33492 (18)	0.0703 (13)
C23	0.84521 (12)	0.4698 (7)	0.27293 (19)	0.0754 (14)
F3A	0.5493 (6)	0.3669 (14)	0.1704 (10)	0.156 (2)	0.197 (6)
F1A	0.5709 (4)	0.581 (2)	0.1264 (8)	0.1148 (16)	0.197 (6)
F2A	0.5040 (3)	0.556 (3)	0.1030 (6)	0.153 (2)	0.197 (6)
Cl1	0.78205 (5)	0.58962 (13)	0.08841 (5)	0.0878 (4)
Cl2	0.81966 (4)	0.89329 (16)	0.34901 (7)	0.0992 (4)
H1B	0.80170	0.47920	0.19100	0.1640*
H5A	0.52150	0.89820	0.13890	0.0960*
H2A	0.81320	0.59790	0.34950	0.0670*
H3A	0.58380	0.52420	0.28050	0.0770*
H1A	0.74020	0.35790	0.40370	0.0630*
H11A	0.56790	0.75720	0.55500	0.1180*
H12A	0.59480	0.60870	0.48890	0.0960*
H15A	0.65200	0.61010	0.45670	0.0760*
H16A	0.65730	0.60030	0.33510	0.0750*
H6A	0.53430	1.12790	0.21730	0.0980*
H9A	0.54740	1.22240	0.45000	0.1070*
H10A	0.54480	1.05820	0.53570	0.1170*
H18A	0.79620	0.50020	0.48620	0.0790*
H18B	0.79410	0.66320	0.43860	0.0790*
H19A	0.85060	0.46350	0.45110	0.0800*
H19B	0.81840	0.29390	0.42710	0.0800*
H20A	0.76480	0.27620	0.31590	0.0730*
H20B	0.76080	0.43360	0.26540	0.0730*
H21A	0.73620	0.64340	0.32030	0.0700*
H21B	0.70610	0.46690	0.30050	0.0700*
H22A	0.84050	0.25350	0.32890	0.0840*
H22B	0.87390	0.40520	0.37060	0.0840*
H23A	0.84330	0.60480	0.27400	0.0900*
H23B	0.87180	0.43780	0.26970	0.0900*
H16B	0.66180	0.41380	0.37420	0.0750*
H17A	0.71910	0.72070	0.41650	0.0690*
H17B	0.72140	0.55860	0.46430	0.0690*

	U11	U22	U33	U12	U13	U23
S	0.0929 (7)	0.0654 (6)	0.1139 (8)	0.0122 (5)	0.0508 (6)	0.0065 (5)
F1B	0.132 (3)	0.112 (3)	0.093 (2)	0.009 (2)	0.041 (2)	−0.020 (2)
F2B	0.246 (6)	0.139 (3)	0.070 (2)	−0.015 (4)	0.064 (3)	0.007 (2)
F3B	0.129 (3)	0.150 (4)	0.156 (4)	−0.058 (3)	0.030 (3)	−0.033 (3)
O1	0.124 (3)	0.129 (3)	0.0652 (16)	−0.048 (2)	0.0302 (17)	−0.0017 (17)
N1	0.0480 (12)	0.0530 (13)	0.0522 (13)	0.0016 (10)	0.0169 (10)	0.0101 (10)
N2	0.0478 (12)	0.0677 (15)	0.0464 (12)	−0.0014 (11)	0.0159 (9)	0.0046 (11)
C1	0.0474 (14)	0.0607 (17)	0.0644 (16)	−0.0007 (13)	0.0237 (12)	0.0043 (14)
C2	0.0438 (13)	0.0623 (17)	0.0693 (18)	0.0024 (12)	0.0269 (12)	0.0100 (15)
C3	0.0514 (15)	0.0686 (19)	0.0668 (18)	−0.0023 (14)	0.0208 (13)	0.0109 (16)
C4	0.0506 (16)	0.085 (2)	0.0688 (19)	−0.0043 (16)	0.0227 (14)	0.0097 (18)
C5	0.0608 (19)	0.106 (3)	0.075 (2)	0.014 (2)	0.0298 (17)	0.032 (2)
C6	0.077 (2)	0.085 (3)	0.094 (3)	0.027 (2)	0.048 (2)	0.037 (2)
C7	0.0565 (17)	0.072 (2)	0.083 (2)	0.0091 (15)	0.0385 (16)	0.0152 (18)
C8	0.0448 (14)	0.084 (2)	0.079 (2)	0.0041 (15)	0.0231 (14)	−0.0116 (19)
C9	0.0517 (18)	0.114 (4)	0.091 (3)	0.011 (2)	0.0202 (17)	−0.025 (3)
C10	0.0555 (19)	0.153 (5)	0.083 (3)	0.001 (3)	0.0279 (18)	−0.033 (3)
C11	0.078 (3)	0.149 (5)	0.073 (2)	−0.024 (3)	0.037 (2)	−0.011 (3)
C12	0.072 (2)	0.102 (3)	0.068 (2)	−0.010 (2)	0.0307 (17)	−0.002 (2)
C13	0.0429 (13)	0.081 (2)	0.0644 (18)	−0.0036 (14)	0.0198 (12)	−0.0025 (16)
C14	0.096 (3)	0.108 (4)	0.067 (2)	−0.014 (3)	0.019 (2)	−0.004 (2)
C15	0.0567 (16)	0.0662 (19)	0.0625 (17)	0.0038 (14)	0.0217 (14)	0.0051 (15)
C16	0.0529 (16)	0.0620 (18)	0.0651 (18)	0.0104 (14)	0.0185 (13)	0.0022 (15)
C17	0.0579 (16)	0.0559 (17)	0.0552 (15)	0.0031 (13)	0.0212 (13)	0.0033 (13)
C18	0.0523 (15)	0.095 (3)	0.0416 (14)	−0.0110 (16)	0.0130 (11)	0.0023 (15)
C19	0.0426 (14)	0.102 (3)	0.0483 (15)	−0.0018 (15)	0.0119 (11)	0.0122 (16)
C20	0.0485 (15)	0.075 (2)	0.0498 (15)	0.0028 (14)	0.0119 (12)	−0.0014 (14)
C21	0.0493 (14)	0.0712 (19)	0.0456 (14)	0.0073 (14)	0.0112 (11)	0.0058 (13)
C22	0.0511 (16)	0.091 (3)	0.0645 (18)	0.0055 (16)	0.0207 (14)	−0.0011 (17)
C23	0.0643 (19)	0.097 (3)	0.072 (2)	−0.0101 (19)	0.0360 (16)	−0.010 (2)
F3A	0.129 (3)	0.150 (4)	0.156 (4)	−0.058 (3)	0.030 (3)	−0.033 (3)
F1A	0.132 (3)	0.112 (3)	0.093 (2)	0.009 (2)	0.041 (2)	−0.020 (2)
F2A	0.246 (6)	0.139 (3)	0.070 (2)	−0.015 (4)	0.064 (3)	0.007 (2)
Cl1	0.1424 (10)	0.0536 (5)	0.0658 (5)	0.0110 (5)	0.0430 (6)	−0.0025 (4)
Cl2	0.0772 (6)	0.0709 (6)	0.1183 (9)	−0.0076 (5)	0.0121 (6)	0.0168 (6)

S—C7	1.745 (3)	C11—C12	1.398 (7)
S—C8	1.768 (4)	C12—C13	1.389 (6)
F1A—C14	1.333 (16)	C15—C16	1.503 (5)
F1B—C14	1.321 (7)	C16—C17	1.513 (5)
F2A—C14	1.318 (13)	C18—C19	1.498 (5)
F2B—C14	1.305 (6)	C20—C21	1.505 (5)
F3A—C14	1.306 (12)	C22—C23	1.520 (6)
F3B—C14	1.337 (7)	C3—H3A	0.9300
O1—C23	1.370 (6)	C5—H5A	0.9300
O1—H1B	0.8200	C6—H6A	0.9300
N1—C18	1.497 (4)	C9—H9A	0.9300
N1—C21	1.494 (4)	C10—H10A	0.9300
N1—C17	1.498 (5)	C11—H11A	0.9300
N2—C19	1.496 (4)	C12—H12A	0.9300
N2—C20	1.488 (4)	C15—H15A	0.9300
N2—C22	1.501 (5)	C16—H16A	0.9700
N1—H1A	0.9100	C16—H16B	0.9700
N2—H2A	0.9100	C17—H17A	0.9700
C1—C13	1.487 (5)	C17—H17B	0.9700
C1—C2	1.503 (4)	C18—H18A	0.9700
C1—C15	1.335 (5)	C18—H18B	0.9700
C2—C7	1.390 (3)	C19—H19A	0.9700
C2—C3	1.390 (3)	C19—H19B	0.9700
C3—C4	1.390 (3)	C20—H20A	0.9700
C4—C14	1.492 (5)	C20—H20B	0.9700
C4—C5	1.390 (4)	C21—H21A	0.9700
C5—C6	1.390 (3)	C21—H21B	0.9700
C6—C7	1.390 (3)	C22—H22A	0.9700
C8—C13	1.394 (6)	C22—H22B	0.9700
C8—C9	1.401 (6)	C23—H23A	0.9700
C9—C10	1.372 (7)	C23—H23B	0.9700
C10—C11	1.355 (10)
C7—S—C8	99.91 (17)	N2—C22—C23	113.0 (3)
C23—O1—H1B	109.00	O1—C23—C22	109.0 (4)
C17—N1—C21	113.8 (2)	C2—C3—H3A	120.00
C18—N1—C21	109.6 (2)	C4—C3—H3A	120.00
C17—N1—C18	110.2 (3)	C4—C5—H5A	120.00
C19—N2—C22	111.1 (3)	C6—C5—H5A	120.00
C20—N2—C22	113.4 (3)	C5—C6—H6A	120.00
C19—N2—C20	108.0 (3)	C7—C6—H6A	120.00
C17—N1—H1A	108.00	C8—C9—H9A	121.00
C18—N1—H1A	108.00	C10—C9—H9A	121.00
C21—N1—H1A	108.00	C9—C10—H10A	119.00
C19—N2—H2A	108.00	C11—C10—H10A	120.00
C20—N2—H2A	108.00	C10—C11—H11A	120.00
C22—N2—H2A	108.00	C12—C11—H11A	120.00
C13—C1—C15	120.8 (3)	C11—C12—H12A	120.00
C2—C1—C13	114.4 (3)	C13—C12—H12A	120.00
C2—C1—C15	124.8 (3)	C1—C15—H15A	116.00
C3—C2—C7	119.99 (17)	C16—C15—H15A	116.00
C1—C2—C3	120.7 (2)	C15—C16—H16A	110.00
C1—C2—C7	119.3 (2)	C15—C16—H16B	110.00
C2—C3—C4	120.01 (16)	C17—C16—H16A	110.00
C3—C4—C5	119.98 (17)	C17—C16—H16B	110.00
C3—C4—C14	120.2 (2)	H16A—C16—H16B	108.00
C5—C4—C14	119.9 (2)	N1—C17—H17A	109.00
C4—C5—C6	120.01 (17)	N1—C17—H17B	109.00
C5—C6—C7	120.0 (2)	C16—C17—H17A	109.00
S—C7—C2	122.40 (17)	C16—C17—H17B	109.00
S—C7—C6	117.57 (17)	H17A—C17—H17B	108.00
C2—C7—C6	120.0 (2)	N1—C18—H18A	109.00
S—C8—C13	121.1 (3)	N1—C18—H18B	109.00
C9—C8—C13	121.2 (4)	C19—C18—H18A	109.00
S—C8—C9	117.7 (3)	C19—C18—H18B	109.00
C8—C9—C10	118.9 (5)	H18A—C18—H18B	108.00
C9—C10—C11	120.9 (5)	N2—C19—H19A	110.00
C10—C11—C12	120.8 (5)	N2—C19—H19B	110.00
C11—C12—C13	120.0 (5)	C18—C19—H19A	110.00
C1—C13—C12	121.6 (4)	C18—C19—H19B	110.00
C1—C13—C8	120.2 (3)	H19A—C19—H19B	108.00
C8—C13—C12	118.2 (4)	N2—C20—H20A	110.00
F1B—C14—F2B	109.4 (5)	N2—C20—H20B	109.00
F1B—C14—F3B	104.5 (5)	C21—C20—H20A	110.00
F1B—C14—C4	113.4 (3)	C21—C20—H20B	110.00
F2B—C14—F3B	106.8 (5)	H20A—C20—H20B	108.00
F2B—C14—C4	113.3 (4)	N1—C21—H21A	109.00
F3B—C14—C4	108.9 (4)	N1—C21—H21B	109.00
F3A—C14—C4	118.2 (9)	C20—C21—H21A	109.00
F1A—C14—C4	103.5 (7)	C20—C21—H21B	109.00
F2A—C14—C4	112.0 (9)	H21A—C21—H21B	108.00
F2A—C14—F3A	108.6 (13)	N2—C22—H22A	109.00
F1A—C14—F2A	106.4 (9)	N2—C22—H22B	109.00
F1A—C14—F3A	107.3 (12)	C23—C22—H22A	109.00
C1—C15—C16	128.4 (3)	C23—C22—H22B	109.00
C15—C16—C17	108.2 (3)	H22A—C22—H22B	108.00
N1—C17—C16	114.1 (3)	O1—C23—H23A	110.00
N1—C18—C19	112.4 (3)	O1—C23—H23B	110.00
N2—C19—C18	109.8 (3)	C22—C23—H23A	110.00
N2—C20—C21	110.7 (3)	C22—C23—H23B	110.00
N1—C21—C20	111.8 (3)	H23A—C23—H23B	108.00
C8—S—C7—C2	−31.8 (3)	C3—C2—C7—C6	0.0 (4)
C8—S—C7—C6	147.3 (2)	C2—C3—C4—C5	0.0 (4)
C7—S—C8—C9	−148.7 (3)	C2—C3—C4—C14	−179.8 (3)
C7—S—C8—C13	31.5 (4)	C3—C4—C5—C6	0.0 (4)
C18—N1—C17—C16	−179.7 (3)	C14—C4—C5—C6	179.8 (3)
C21—N1—C17—C16	56.7 (4)	C3—C4—C14—F1B	−25.0 (5)
C17—N1—C18—C19	−179.9 (3)	C3—C4—C14—F2B	−150.5 (4)
C21—N1—C18—C19	−53.9 (4)	C3—C4—C14—F3B	90.8 (4)
C17—N1—C21—C20	176.9 (3)	C5—C4—C14—F1B	155.2 (4)
C18—N1—C21—C20	53.0 (4)	C5—C4—C14—F2B	29.8 (6)
C20—N2—C19—C18	−60.8 (4)	C5—C4—C14—F3B	−89.0 (4)
C22—N2—C19—C18	174.2 (3)	C4—C5—C6—C7	0.0 (4)
C19—N2—C20—C21	60.8 (4)	C5—C6—C7—S	−179.1 (2)
C22—N2—C20—C21	−175.6 (3)	C5—C6—C7—C2	0.0 (4)
C19—N2—C22—C23	−164.1 (3)	S—C8—C9—C10	180.0 (4)
C20—N2—C22—C23	74.0 (4)	C13—C8—C9—C10	−0.2 (6)
C13—C1—C2—C3	−138.9 (3)	S—C8—C13—C1	1.5 (5)
C13—C1—C2—C7	41.1 (4)	S—C8—C13—C12	−179.7 (3)
C15—C1—C2—C3	42.8 (5)	C9—C8—C13—C1	−178.4 (4)
C15—C1—C2—C7	−137.2 (3)	C9—C8—C13—C12	0.5 (6)
C2—C1—C13—C8	−41.3 (5)	C8—C9—C10—C11	−0.2 (7)
C2—C1—C13—C12	139.9 (4)	C9—C10—C11—C12	0.2 (8)
C15—C1—C13—C8	137.1 (4)	C10—C11—C12—C13	0.1 (7)
C15—C1—C13—C12	−41.7 (6)	C11—C12—C13—C1	178.4 (4)
C2—C1—C15—C16	4.3 (6)	C11—C12—C13—C8	−0.4 (6)
C13—C1—C15—C16	−173.9 (4)	C1—C15—C16—C17	132.6 (4)
C1—C2—C3—C4	180.0 (2)	C15—C16—C17—N1	169.2 (3)
C7—C2—C3—C4	0.0 (4)	N1—C18—C19—N2	58.8 (4)
C1—C2—C7—S	−0.9 (3)	N2—C20—C21—N1	−58.1 (4)
C1—C2—C7—C6	−180.0 (3)	N2—C22—C23—O1	−75.4 (5)
C3—C2—C7—S	179.1 (2)

Cg1 and Cg2 are the centroids of the C2–C7 and C8–C13 benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···Cl1i	0.91	2.10	2.997 (3)	168
O1—H1B···Cl1	0.82	2.27	3.030 (4)	155
N2—H2A···Cl2	0.91	2.13	3.035 (3)	175
C17—H17A···Cl1ii	0.97	2.64	3.600 (4)	169
C18—H18A···Cl1iii	0.97	2.64	3.561 (3)	159
C20—H20B···O1	0.97	2.34	2.999 (6)	125
C21—H21A···O1ii	0.97	2.35	3.153 (6)	140
C22—H22A···Cl2iv	0.97	2.77	3.690 (4)	160
C19—H19A···Cg2v	0.97	2.65	3.618 (4)	176
C23—H23B···Cg1i	0.97	2.69	3.658 (5)	174

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C2–C7 and C8–C13 benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯Cl1i	0.91	2.10	2.997 (3)	168
O1—H1B⋯Cl1	0.82	2.27	3.030 (4)	155
N2—H2A⋯Cl2	0.91	2.13	3.035 (3)	175
C17—H17A⋯Cl1ii	0.97	2.64	3.600 (4)	169
C18—H18A⋯Cl1iii	0.97	2.64	3.561 (3)	159
C20—H20B⋯O1	0.97	2.34	2.999 (6)	125
C21—H21A⋯O1ii	0.97	2.35	3.153 (6)	140
C22—H22A⋯Cl2iv	0.97	2.77	3.690 (4)	160
C19—H19A⋯Cg2v	0.97	2.65	3.618 (4)	176
C23—H23B⋯Cg1i	0.97	2.69	3.658 (5)	174

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