1-[(4-Chloro-phen-yl)(phen-yl)meth-yl]piperazine-1,4-diium bis-(trichloro-acetate)-trichloro-acetic acid (1/1).

In the title salt adduct, C(17)H(21)ClN(2) (2+)·2C(2)Cl(3)O(2) (-)·C(2)HCl(3)O(2), the Cl atom of the dication is disordered over two positions in a 0.915 (3):0.085 (3) ratio. The Cl atoms in the trichloroacetate anions and trichloroacetic acid molecule are also disordered, with refined site-occupation factors of 0.59 (3):0.41 (3), 0.503 (12):0.417 (12) and 0.653 (12):0.347 (12). The piperazine ring adopts a chair conformation, with puckering parameters Q(T) = 0.587 (3) Å, θ = 2.6 (2) and Φ 334 (6)°. In the crystal, neighbouring mol-ecules are linked by N-H⋯O, O-H⋯O, N-H⋯Cl, C-H⋯O and C-H⋯Cl hydrogen bonds, forming a three-dimensional network.

Related literature

For the biological activity of piperazine derivatives, see: Dinsmore et al. (2002 ▶); Berkheij et al. (2005 ▶); Humle & Cherrier (1999 ▶); Campbell et al. (1973 ▶). For related structures, see: Jasinski et al. (2011 ▶); Song et al. (2012 ▶). For puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C17H21ClN2 2+·2C2Cl3O2 −·C2HCl3O2

M = 776.93

Triclinic,

a = 9.746 (2) Å

b = 13.096 (3) Å

c = 13.725 (3) Å

α = 88.317 (3)°

β = 73.127 (3)°

γ = 77.169 (3)°

V = 1633.3 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.89 mm−1

T = 293 K

0.27 × 0.22 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2004) ▶ T min = 0.790, T max = 0.875

10010 measured reflections

7039 independent reflections

5186 reflections with I > 2σ(I)

R int = 0.012

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.125

S = 1.04

7039 reflections

468 parameters

38 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.33 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812034794/fj2574sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812034794/fj2574Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812034794/fj2574Isup3.cml

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

C17H21ClN22+·2C2Cl3O2−·C2HCl3O2	Z = 2
Mr = 776.93	F(000) = 784
Triclinic, P1	Dx = 1.580 Mg m−3
Hall symbol: -P 1	Melting point = 409–411 K
a = 9.746 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 13.096 (3) Å	Cell parameters from 3555 reflections
c = 13.725 (3) Å	θ = 2.2–26.9°
α = 88.317 (3)°	µ = 0.89 mm−1
β = 73.127 (3)°	T = 293 K
γ = 77.169 (3)°	Plate, colourless
V = 1633.3 (6) Å3	0.27 × 0.22 × 0.15 mm

Bruker APEXII CCD diffractometer	7039 independent reflections
Radiation source: fine-focus sealed tube	5186 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.012
φ and ω scans	θmax = 27.2°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2004)	h = −11→12
Tmin = 0.790, Tmax = 0.875	k = −16→11
10010 measured reflections	l = −16→17

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.125	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0496P)2 + 0.7913P] where P = (Fo2 + 2Fc2)/3
7039 reflections	(Δ/σ)max = 0.001
468 parameters	Δρmax = 0.40 e Å−3
38 restraints	Δρmin = −0.33 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)
Cl1C	0.31840 (14)	0.07626 (8)	0.67451 (7)	0.1062 (4)	0.915 (3)
N1	0.66237 (18)	0.23191 (14)	0.21015 (13)	0.0366 (5)
N2	0.7247 (2)	0.14402 (17)	0.00697 (14)	0.0500 (6)
C1	0.3636 (3)	0.2436 (2)	0.42747 (18)	0.0496 (8)
C2	0.3041 (3)	0.1922 (2)	0.5133 (2)	0.0623 (10)
C3	0.3952 (4)	0.1382 (2)	0.5661 (2)	0.0614 (9)
C4	0.5441 (4)	0.1344 (2)	0.5345 (2)	0.0672 (10)
C5	0.6024 (3)	0.1857 (2)	0.4488 (2)	0.0545 (8)
C6	0.5126 (2)	0.24114 (17)	0.39409 (16)	0.0391 (6)
C7	0.5689 (2)	0.30362 (17)	0.30255 (16)	0.0386 (6)
C8	0.6491 (3)	0.38233 (17)	0.32521 (16)	0.0417 (7)
C9	0.7969 (3)	0.3582 (2)	0.3198 (2)	0.0544 (8)
C10	0.8610 (3)	0.4331 (2)	0.3469 (2)	0.0643 (10)
C11	0.7786 (4)	0.5318 (3)	0.3801 (2)	0.0690 (11)
C12	0.6326 (4)	0.5560 (2)	0.3859 (2)	0.0671 (10)
C13	0.5666 (3)	0.48247 (19)	0.35811 (19)	0.0532 (8)
C14	0.7043 (3)	0.2947 (2)	0.11745 (17)	0.0472 (8)
C15	0.8003 (3)	0.2238 (2)	0.02683 (18)	0.0555 (9)
C16	0.6808 (3)	0.08220 (19)	0.09830 (18)	0.0478 (8)
C17	0.5831 (2)	0.15348 (18)	0.18780 (17)	0.0416 (7)
Cl1D	0.8762 (17)	0.5906 (10)	0.4249 (12)	0.123 (6)	0.085 (3)
Cl1B	0.6717 (5)	0.2921 (6)	0.7725 (6)	0.0945 (12)	0.59 (3)
Cl2B	0.9718 (4)	0.2936 (7)	0.7561 (5)	0.0923 (13)	0.59 (3)
Cl3B	0.8561 (7)	0.3498 (10)	0.5860 (4)	0.129 (2)	0.59 (3)
O1	0.7348 (4)	0.46222 (19)	0.8666 (2)	0.0975 (10)
O2	0.7545 (3)	0.5423 (2)	0.7197 (2)	0.1045 (11)
C18	0.7641 (3)	0.4663 (3)	0.7690 (3)	0.0725 (11)
C19	0.8137 (3)	0.3552 (3)	0.7202 (2)	0.0700 (10)
Cl1A	0.6634 (9)	0.2930 (7)	0.7508 (14)	0.121 (3)	0.41 (3)
Cl2A	0.9600 (10)	0.2728 (12)	0.7519 (6)	0.116 (2)	0.41 (3)
Cl3A	0.8603 (7)	0.3771 (15)	0.5911 (6)	0.104 (3)	0.41 (3)
Cl4B	1.1554 (7)	0.1768 (5)	0.2833 (10)	0.163 (3)	0.503 (12)
Cl5B	1.0936 (7)	−0.0153 (9)	0.3672 (4)	0.146 (3)	0.503 (12)
Cl6B	1.3218 (4)	−0.0180 (4)	0.1815 (4)	0.0598 (10)	0.503 (12)
O3	0.90549 (18)	0.11171 (14)	0.24280 (14)	0.0588 (6)
O4	1.05566 (19)	−0.00573 (16)	0.12532 (14)	0.0631 (7)
C20	1.0244 (2)	0.05258 (18)	0.19980 (17)	0.0406 (7)
C21	1.1464 (3)	0.0551 (2)	0.25207 (19)	0.0537 (8)
Cl4A	1.1704 (3)	0.1899 (2)	0.2413 (3)	0.0618 (8)	0.497 (12)
Cl5A	1.0917 (8)	0.0294 (5)	0.3806 (3)	0.1017 (17)	0.497 (12)
Cl6A	1.3180 (5)	−0.0238 (5)	0.1946 (6)	0.0861 (16)	0.497 (12)
Cl7A	0.8144 (3)	0.8071 (2)	0.0564 (3)	0.0937 (8)	0.653 (12)
Cl8A	0.7410 (4)	0.6177 (5)	0.1419 (3)	0.1097 (12)	0.653 (12)
Cl9A	0.9218 (3)	0.6188 (3)	−0.0657 (2)	0.0773 (8)	0.653 (12)
O5	0.5411 (2)	0.79751 (16)	0.02795 (15)	0.0696 (7)
O6	0.6096 (3)	0.6471 (2)	−0.0567 (2)	0.1044 (13)
C22	0.6253 (3)	0.7137 (2)	−0.0029 (2)	0.0565 (9)
C23	0.7680 (3)	0.6882 (2)	0.0312 (2)	0.0588 (9)
Cl7B	0.7846 (14)	0.7855 (7)	0.1020 (12)	0.155 (4)	0.347 (12)
Cl8B	0.7349 (10)	0.5792 (8)	0.1111 (9)	0.134 (3)	0.347 (12)
Cl9B	0.9191 (8)	0.6431 (10)	−0.0692 (6)	0.141 (3)	0.347 (12)
H1	0.30230	0.28060	0.39140	0.0590*
H1A	0.74610	0.19660	0.22360	0.0440*
H1C	0.812 (7)	0.587 (4)	0.400 (5)	0.1680*	0.915 (3)
H2	0.20380	0.19420	0.53480	0.0750*
H2A	0.78510	0.10080	−0.04520	0.0600*
H2B	0.64430	0.17580	−0.01100	0.0600*
H4	0.60480	0.09750	0.57100	0.0810*
H5	0.70280	0.18320	0.42730	0.0650*
H7	0.48250	0.34370	0.28470	0.0460*
H9	0.85350	0.29140	0.29790	0.0650*
H10	0.96050	0.41640	0.34260	0.0770*
H12	0.57670	0.62280	0.40870	0.0810*
H13	0.46750	0.50020	0.36150	0.0640*
H14A	0.75700	0.34490	0.13060	0.0570*
H14B	0.61620	0.33320	0.10230	0.0570*
H15A	0.82360	0.26550	−0.03280	0.0670*
H15B	0.89180	0.18940	0.03990	0.0670*
H16A	0.76800	0.04370	0.11480	0.0570*
H16B	0.62870	0.03200	0.08420	0.0570*
H17A	0.49400	0.18980	0.17250	0.0500*
H17B	0.55550	0.11210	0.24720	0.0500*
H1D	0.35640	0.10400	0.62340	0.1680*	0.085 (3)
H1B	0.69470	0.52090	0.89260	0.1460*

	U11	U22	U33	U12	U13	U23
Cl1C	0.1343 (10)	0.0734 (6)	0.0679 (6)	−0.0027 (6)	0.0188 (6)	0.0294 (5)
N1	0.0324 (9)	0.0402 (10)	0.0346 (9)	−0.0041 (7)	−0.0085 (7)	−0.0037 (8)
N2	0.0382 (10)	0.0655 (13)	0.0387 (10)	0.0035 (9)	−0.0094 (8)	−0.0153 (10)
C1	0.0481 (13)	0.0562 (15)	0.0428 (13)	−0.0120 (11)	−0.0102 (11)	−0.0012 (11)
C2	0.0619 (17)	0.0661 (18)	0.0532 (16)	−0.0233 (14)	−0.0007 (13)	−0.0032 (14)
C3	0.082 (2)	0.0423 (14)	0.0446 (14)	−0.0083 (13)	0.0010 (13)	0.0017 (11)
C4	0.080 (2)	0.0580 (17)	0.0522 (16)	0.0059 (15)	−0.0186 (15)	0.0086 (13)
C5	0.0497 (14)	0.0539 (15)	0.0510 (14)	0.0012 (11)	−0.0103 (11)	0.0011 (12)
C6	0.0423 (11)	0.0369 (11)	0.0340 (11)	−0.0053 (9)	−0.0068 (9)	−0.0072 (9)
C7	0.0366 (11)	0.0367 (11)	0.0367 (11)	0.0004 (9)	−0.0075 (9)	−0.0056 (9)
C8	0.0485 (13)	0.0367 (12)	0.0354 (11)	−0.0076 (10)	−0.0065 (9)	−0.0036 (9)
C9	0.0510 (14)	0.0475 (14)	0.0624 (16)	−0.0082 (11)	−0.0136 (12)	−0.0141 (12)
C10	0.0616 (17)	0.0729 (19)	0.0616 (17)	−0.0269 (15)	−0.0128 (14)	−0.0095 (15)
C11	0.088 (2)	0.0628 (19)	0.0562 (17)	−0.0337 (17)	−0.0069 (15)	−0.0114 (14)
C12	0.092 (2)	0.0397 (14)	0.0586 (17)	−0.0133 (14)	−0.0047 (15)	−0.0111 (12)
C13	0.0621 (15)	0.0418 (13)	0.0460 (14)	−0.0038 (11)	−0.0060 (12)	−0.0042 (11)
C14	0.0481 (13)	0.0535 (14)	0.0389 (12)	−0.0147 (11)	−0.0083 (10)	0.0018 (11)
C15	0.0471 (14)	0.0763 (18)	0.0388 (13)	−0.0162 (13)	−0.0034 (11)	−0.0066 (12)
C16	0.0431 (12)	0.0468 (13)	0.0516 (14)	−0.0019 (10)	−0.0155 (11)	−0.0127 (11)
C17	0.0404 (11)	0.0413 (12)	0.0419 (12)	−0.0070 (9)	−0.0110 (9)	−0.0054 (10)
Cl1D	0.138 (13)	0.084 (8)	0.122 (11)	−0.057 (8)	0.028 (9)	−0.043 (8)
Cl1B	0.087 (2)	0.092 (2)	0.103 (2)	−0.0406 (17)	−0.0098 (14)	0.0010 (15)
Cl2B	0.0502 (18)	0.125 (3)	0.080 (2)	0.010 (2)	−0.0111 (14)	0.039 (2)
Cl3B	0.166 (5)	0.130 (4)	0.0581 (17)	0.026 (3)	−0.0279 (19)	0.0032 (17)
O1	0.128 (2)	0.0724 (16)	0.0876 (18)	−0.0050 (15)	−0.0374 (16)	0.0014 (13)
O2	0.1013 (19)	0.0807 (17)	0.136 (2)	−0.0134 (14)	−0.0510 (17)	0.0464 (17)
C18	0.0613 (18)	0.073 (2)	0.089 (2)	−0.0147 (15)	−0.0330 (17)	0.0250 (18)
C19	0.0590 (17)	0.078 (2)	0.0604 (17)	0.0002 (15)	−0.0106 (14)	0.0138 (15)
Cl1A	0.121 (4)	0.069 (3)	0.162 (8)	−0.018 (3)	−0.027 (4)	−0.015 (3)
Cl2A	0.114 (5)	0.116 (4)	0.061 (3)	0.062 (4)	−0.003 (3)	0.007 (3)
Cl3A	0.083 (3)	0.146 (7)	0.064 (3)	0.000 (3)	−0.0147 (18)	0.027 (3)
Cl4B	0.124 (3)	0.115 (3)	0.274 (7)	0.028 (2)	−0.125 (4)	−0.117 (3)
Cl5B	0.096 (3)	0.252 (8)	0.0563 (17)	0.034 (4)	−0.0272 (15)	0.028 (3)
Cl6B	0.0251 (13)	0.075 (2)	0.0773 (16)	−0.0025 (13)	−0.0156 (11)	−0.0275 (15)
O3	0.0395 (9)	0.0604 (11)	0.0696 (12)	0.0093 (8)	−0.0186 (8)	−0.0206 (9)
O4	0.0446 (9)	0.0845 (14)	0.0543 (11)	0.0062 (9)	−0.0178 (8)	−0.0291 (10)
C20	0.0333 (11)	0.0433 (12)	0.0435 (12)	−0.0024 (9)	−0.0130 (9)	−0.0005 (10)
C21	0.0441 (13)	0.0605 (16)	0.0550 (15)	0.0020 (11)	−0.0213 (11)	−0.0107 (12)
Cl4A	0.0429 (12)	0.0478 (11)	0.0974 (18)	−0.0109 (7)	−0.0229 (11)	−0.0082 (12)
Cl5A	0.102 (3)	0.165 (4)	0.0475 (15)	−0.038 (3)	−0.0323 (15)	0.0251 (18)
Cl6A	0.060 (2)	0.075 (2)	0.121 (4)	0.0152 (18)	−0.045 (2)	−0.003 (2)
Cl7A	0.0516 (10)	0.0767 (12)	0.146 (2)	−0.0045 (8)	−0.0225 (13)	−0.0295 (13)
Cl8A	0.0871 (13)	0.160 (3)	0.0825 (15)	−0.0239 (17)	−0.0334 (12)	0.0591 (18)
Cl9A	0.0466 (12)	0.0750 (12)	0.0865 (15)	0.0172 (9)	−0.0047 (9)	−0.0106 (9)
O5	0.0487 (10)	0.0748 (13)	0.0735 (13)	0.0149 (10)	−0.0203 (9)	−0.0066 (11)
O6	0.0810 (16)	0.0876 (17)	0.154 (3)	0.0089 (13)	−0.0651 (17)	−0.0407 (17)
C22	0.0419 (13)	0.0611 (17)	0.0591 (16)	0.0008 (12)	−0.0131 (12)	0.0056 (13)
C23	0.0454 (14)	0.0588 (16)	0.0644 (17)	0.0045 (12)	−0.0164 (12)	0.0032 (13)
Cl7B	0.156 (7)	0.118 (5)	0.214 (9)	0.051 (4)	−0.144 (6)	−0.083 (5)
Cl8B	0.139 (4)	0.125 (5)	0.112 (5)	0.020 (3)	−0.039 (3)	0.058 (4)
Cl9B	0.053 (3)	0.189 (7)	0.167 (6)	−0.035 (4)	0.000 (3)	−0.060 (5)

Cl1C—C3	1.728 (3)	C2—C3	1.370 (4)
Cl1D—C11	1.603 (17)	C3—C4	1.379 (6)
Cl1A—C19	1.772 (11)	C4—C5	1.376 (4)
Cl1B—C19	1.735 (7)	C5—C6	1.387 (4)
Cl2A—C19	1.742 (13)	C6—C7	1.513 (3)
Cl2B—C19	1.770 (7)	C7—C8	1.513 (3)
Cl3A—C19	1.729 (9)	C8—C9	1.385 (4)
Cl3B—C19	1.767 (6)	C8—C13	1.388 (3)
Cl4A—C21	1.828 (4)	C9—C10	1.385 (4)
Cl4B—C21	1.690 (8)	C10—C11	1.373 (5)
Cl5A—C21	1.735 (5)	C11—C12	1.366 (6)
Cl5B—C21	1.807 (8)	C12—C13	1.388 (4)
Cl6A—C21	1.732 (7)	C14—C15	1.514 (3)
Cl6B—C21	1.773 (6)	C16—C17	1.510 (3)
Cl7A—C23	1.784 (4)	C1—H1	0.9300
Cl7B—C23	1.688 (13)	C2—H2	0.9300
Cl8A—C23	1.739 (5)	C3—H1D	0.9200
Cl8B—C23	1.803 (11)	C4—H4	0.9300
Cl9A—C23	1.775 (4)	C5—H5	0.9300
Cl9B—C23	1.703 (9)	C7—H7	0.9800
O1—C18	1.288 (5)	C9—H9	0.9300
O2—C18	1.189 (5)	C10—H10	0.9300
O1—H1B	0.8200	C11—H1C	0.93 (6)
O3—C20	1.234 (3)	C12—H12	0.9300
O4—C20	1.218 (3)	C13—H13	0.9300
O5—C22	1.218 (3)	C14—H14B	0.9700
O6—C22	1.222 (4)	C14—H14A	0.9700
N1—C17	1.502 (3)	C15—H15B	0.9700
N1—C14	1.499 (3)	C15—H15A	0.9700
N1—C7	1.530 (3)	C16—H16A	0.9700
N2—C16	1.481 (3)	C16—H16B	0.9700
N2—C15	1.478 (4)	C17—H17B	0.9700
N1—H1A	0.9100	C17—H17A	0.9700
N2—H2B	0.9000	C18—C19	1.535 (5)
N2—H2A	0.9000	C20—C21	1.563 (4)
C1—C2	1.381 (4)	C22—C23	1.558 (4)
C1—C6	1.383 (4)
C18—O1—H1B	110.00	C15—C14—H14A	109.00
C7—N1—C17	111.81 (16)	C15—C14—H14B	110.00
C14—N1—C17	108.77 (17)	N1—C14—H14B	110.00
C7—N1—C14	110.75 (17)	H14A—C14—H14B	108.00
C15—N2—C16	111.02 (19)	N2—C15—H15B	110.00
C17—N1—H1A	109.00	C14—C15—H15A	109.00
C7—N1—H1A	108.00	C14—C15—H15B	110.00
C14—N1—H1A	108.00	H15A—C15—H15B	108.00
C16—N2—H2A	109.00	N2—C15—H15A	110.00
C16—N2—H2B	109.00	N2—C16—H16B	110.00
H2A—N2—H2B	108.00	C17—C16—H16A	110.00
C15—N2—H2B	109.00	N2—C16—H16A	110.00
C15—N2—H2A	109.00	H16A—C16—H16B	108.00
C2—C1—C6	121.3 (3)	C17—C16—H16B	110.00
C1—C2—C3	119.0 (3)	N1—C17—H17A	110.00
C2—C3—C4	121.0 (3)	N1—C17—H17B	110.00
Cl1C—C3—C4	120.7 (2)	C16—C17—H17B	110.00
Cl1C—C3—C2	118.3 (3)	H17A—C17—H17B	108.00
C3—C4—C5	119.6 (3)	C16—C17—H17A	110.00
C4—C5—C6	120.5 (3)	O1—C18—C19	110.2 (3)
C1—C6—C5	118.6 (2)	O2—C18—C19	122.1 (3)
C1—C6—C7	118.4 (2)	O1—C18—O2	127.6 (4)
C5—C6—C7	123.0 (2)	Cl1B—C19—Cl2B	110.1 (4)
N1—C7—C6	111.45 (17)	Cl1B—C19—Cl3B	109.5 (4)
C6—C7—C8	112.71 (17)	Cl2B—C19—Cl3B	109.3 (4)
N1—C7—C8	111.75 (17)	Cl2B—C19—C18	106.4 (3)
C7—C8—C9	123.6 (2)	Cl1B—C19—C18	106.7 (3)
C9—C8—C13	119.0 (2)	Cl1A—C19—C18	109.9 (5)
C7—C8—C13	117.3 (3)	Cl2A—C19—C18	116.1 (5)
C8—C9—C10	120.3 (2)	Cl3A—C19—C18	103.2 (7)
C9—C10—C11	120.4 (3)	Cl1A—C19—Cl2A	108.3 (6)
Cl1D—C11—C12	131.9 (6)	Cl1A—C19—Cl3A	108.3 (7)
Cl1D—C11—C10	107.6 (6)	Cl2A—C19—Cl3A	110.7 (5)
C10—C11—C12	119.5 (3)	Cl3B—C19—C18	114.8 (5)
C11—C12—C13	121.0 (3)	O3—C20—O4	128.7 (2)
C8—C13—C12	119.8 (3)	O3—C20—C21	113.0 (2)
N1—C14—C15	110.6 (2)	O4—C20—C21	118.3 (2)
N2—C15—C14	110.7 (2)	Cl4B—C21—Cl5B	109.1 (5)
N2—C16—C17	110.42 (19)	Cl4B—C21—Cl6B	111.0 (4)
N1—C17—C16	110.10 (19)	Cl4B—C21—C20	114.3 (3)
C2—C1—H1	119.00	Cl5B—C21—Cl6B	105.5 (4)
C6—C1—H1	119.00	Cl5B—C21—C20	103.6 (3)
C3—C2—H2	121.00	Cl6B—C21—C20	112.6 (2)
C1—C2—H2	120.00	Cl4A—C21—C20	104.9 (2)
C2—C3—H1D	119.00	Cl5A—C21—C20	112.1 (3)
C4—C3—H1D	120.00	Cl6A—C21—C20	115.9 (3)
C5—C4—H4	120.00	Cl4A—C21—Cl5A	107.8 (3)
C3—C4—H4	120.00	Cl4A—C21—Cl6A	106.1 (3)
C4—C5—H5	120.00	Cl5A—C21—Cl6A	109.6 (4)
C6—C5—H5	120.00	O5—C22—O6	127.3 (3)
N1—C7—H7	107.00	O5—C22—C23	116.3 (2)
C6—C7—H7	107.00	O6—C22—C23	116.5 (3)
C8—C7—H7	107.00	Cl7A—C23—Cl8A	108.5 (3)
C10—C9—H9	120.00	Cl7A—C23—Cl9A	105.8 (2)
C8—C9—H9	120.00	Cl7A—C23—C22	109.7 (2)
C9—C10—H10	120.00	Cl8A—C23—Cl9A	110.3 (3)
C11—C10—H10	120.00	Cl8A—C23—C22	110.3 (2)
C12—C11—H1C	114 (4)	Cl9A—C23—C22	112.1 (2)
C10—C11—H1C	127 (4)	Cl7B—C23—C22	113.7 (5)
C11—C12—H12	119.00	Cl8B—C23—C22	100.1 (4)
C13—C12—H12	120.00	Cl9B—C23—C22	111.2 (3)
C12—C13—H13	120.00	Cl7B—C23—Cl8B	108.9 (6)
C8—C13—H13	120.00	Cl7B—C23—Cl9B	114.1 (6)
N1—C14—H14A	110.00	Cl8B—C23—Cl9B	107.7 (6)
C17—N1—C14—C15	−58.3 (3)	C9—C8—C13—C12	−0.7 (4)
C14—N1—C7—C8	−58.7 (2)	C7—C8—C13—C12	176.1 (2)
C17—N1—C7—C8	179.79 (17)	C13—C8—C9—C10	0.0 (4)
C14—N1—C17—C16	59.2 (2)	C7—C8—C9—C10	−176.6 (2)
C14—N1—C7—C6	174.17 (19)	C8—C9—C10—C11	0.5 (4)
C7—N1—C17—C16	−178.22 (18)	C9—C10—C11—C12	−0.3 (4)
C7—N1—C14—C15	178.4 (2)	C10—C11—C12—C13	−0.4 (4)
C17—N1—C7—C6	52.7 (2)	C11—C12—C13—C8	0.9 (4)
C16—N2—C15—C14	−56.4 (3)	N1—C14—C15—N2	57.3 (3)
C15—N2—C16—C17	57.4 (3)	N2—C16—C17—N1	−59.0 (3)
C2—C1—C6—C7	−177.0 (2)	O1—C18—C19—Cl1B	58.1 (4)
C6—C1—C2—C3	0.2 (4)	O1—C18—C19—Cl2B	−59.4 (4)
C2—C1—C6—C5	−0.1 (4)	O1—C18—C19—Cl3B	179.6 (4)
C1—C2—C3—Cl1C	178.9 (2)	O2—C18—C19—Cl1B	−121.0 (4)
C1—C2—C3—C4	−0.2 (4)	O2—C18—C19—Cl2B	121.5 (4)
Cl1C—C3—C4—C5	−179.0 (2)	O2—C18—C19—Cl3B	0.4 (5)
C2—C3—C4—C5	0.1 (4)	O3—C20—C21—Cl4B	−45.2 (5)
C3—C4—C5—C6	0.0 (4)	O3—C20—C21—Cl5B	73.4 (4)
C4—C5—C6—C1	−0.1 (4)	O3—C20—C21—Cl6B	−173.0 (2)
C4—C5—C6—C7	176.8 (2)	O4—C20—C21—Cl4B	135.6 (5)
C5—C6—C7—C8	−54.2 (3)	O4—C20—C21—Cl5B	−105.8 (4)
C1—C6—C7—C8	122.6 (2)	O4—C20—C21—Cl6B	7.7 (3)
C5—C6—C7—N1	72.4 (3)	O5—C22—C23—Cl7A	−26.7 (3)
C1—C6—C7—N1	−110.8 (2)	O5—C22—C23—Cl8A	92.7 (3)
C6—C7—C8—C9	85.5 (3)	O5—C22—C23—Cl9A	−144.0 (2)
N1—C7—C8—C9	−40.9 (3)	O6—C22—C23—Cl7A	154.0 (3)
N1—C7—C8—C13	142.5 (2)	O6—C22—C23—Cl8A	−86.7 (3)
C6—C7—C8—C13	−91.1 (2)	O6—C22—C23—Cl9A	36.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3	0.91	1.78	2.685 (3)	172
O1—H1B···O6i	0.82	1.74	2.560 (4)	178
N2—H2A···Cl6Bii	0.90	2.74	3.299 (5)	121
N2—H2A···O4ii	0.90	1.84	2.716 (3)	162
N2—H2B···O5iii	0.90	1.84	2.710 (3)	161
C7—H7···O2iv	0.98	2.47	3.435 (4)	167
C9—H9···O3	0.93	2.39	3.270 (3)	157
C14—H14B···O6iii	0.97	2.42	3.323 (4)	156
C15—H15B···Cl7Av	0.97	2.79	3.526 (5)	133

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O3	0.91	1.78	2.685 (3)	172
O1—H1B⋯O6i	0.82	1.74	2.560 (4)	178
N2—H2A⋯Cl6B ii	0.90	2.74	3.299 (5)	121
N2—H2A⋯O4ii	0.90	1.84	2.716 (3)	162
N2—H2B⋯O5iii	0.90	1.84	2.710 (3)	161
C7—H7⋯O2iv	0.98	2.47	3.435 (4)	167
C9—H9⋯O3	0.93	2.39	3.270 (3)	157
C14—H14B⋯O6iii	0.97	2.42	3.323 (4)	156
C15—H15B⋯Cl7A v	0.97	2.79	3.526 (5)	133

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