Triprolidinium dichloranilate-chloranilic acid-methanol-water (2/1/2/2).

In the triprolidinium cation of the title compound {systematic name: 2-[1-(4-methyl-phen-yl)-3-(pyrrolidin-1-ium-1-yl)prop-1-en-1-yl]pyridin-1-ium bis-(2,5-dichloro-4-hy-droxy-3,6-dioxo-cyclo-hexa-1,4-dien-1-olate)-2,5-dichloro-3,6-dihy-droxy-cyclo-hexa-2,5-diene-1,4-dione-methanol-water (2/1/2/2)}, C(19)H(24)N(2) (2+)·2C(6)HCl(2)O(4) (-)·0.5C(6)H(2)Cl(2)O(4)·CH(3)OH·H(2)O, the N atoms on both the pyrrolidine and pyridine groups are protonated. The neutral chloranilic acid mol-ecule is on an inversion symmetry element and its hy-droxy H atoms are disordered over two positions with site-occupancy factors of 0.53 (6) and 0.47 (6). The methanol solvent mol-ecule is disordered over two positions in a 0.836 (4):0.164 (4) ratio. In the crystal, N-H⋯O, O-H⋯O and C-H⋯O inter-actions link the components. The crystal structure also features π-π inter-actions between the benzene rings [centroid-centroid distances = 3.5674 (15), 3.5225 (15) and 3.6347 (15) Å].

Related literature

For the synthesis and spectroscopic studies of charge-transfer complexes between chloranilic acid and some heterocyclic amines in ethanol, see: Al-Attas et al. (2009 ▶). For spectroscopic studies of the inter­action between triprolidine hydro­chloride and serum albumins, see: Sandhya et al. (2011 ▶). For related structures, see: Adam et al. (2010 ▶); Dayananda et al. (2011 ▶); Dutkiewicz et al. (2010 ▶); Gotoh et al. (2010 ▶); Hakim Al-arique et al. (2010 ▶); Jasinski et al. (2010 ▶); Parvez & Sabir (1997 ▶); Udachin et al. (2011 ▶). For ring puckering parameters, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C19H24N2 2+·2C6HCl2O4 −·0.5C6H2Cl2O4·CH4O·H2O

M = 850.88

Monoclinic,

a = 9.1633 (2) Å

b = 32.3720 (7) Å

c = 12.9834 (4) Å

β = 106.685 (3)°

V = 3689.17 (17) Å3

Z = 4

Cu Kα radiation

μ = 4.16 mm−1

T = 123 K

0.5 × 0.38 × 0.12 mm

Data collection

Agilent Xcalibur Ruby Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ▶) T min = 0.188, T max = 0.607

25133 measured reflections

7532 independent reflections

6721 reflections with I > 2σ(I)

R int = 0.036

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.137

S = 1.08

7532 reflections

510 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.08 e Å−3

Δρmin = −0.29 e Å−3

Data collection: CrysAlis PRO (Agilent, 2011 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Agilent, 2011 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812010136/bt5841sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812010136/bt5841Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812010136/bt5841Isup3.cml

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

C19H24N22+·2C6HCl2O4−·0.5C6H2Cl2O4·CH4O·H2O	F(000) = 1752
Mr = 850.88	Dx = 1.532 Mg m−3
Monoclinic, P21/n	Cu Kα radiation, λ = 1.54184 Å
Hall symbol: -P 2yn	Cell parameters from 10725 reflections
a = 9.1633 (2) Å	θ = 2.7–75.5°
b = 32.3720 (7) Å	µ = 4.16 mm−1
c = 12.9834 (4) Å	T = 123 K
β = 106.685 (3)°	Plate, dark brown
V = 3689.17 (17) Å3	0.5 × 0.38 × 0.12 mm
Z = 4

Agilent Xcalibur Ruby Gemini diffractometer	7532 independent reflections
Radiation source: Enhance (Cu) X-ray Source	6721 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.036
Detector resolution: 10.5081 pixels mm-1	θmax = 75.7°, θmin = 2.7°
ω scans	h = −9→11
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −39→40
Tmin = 0.188, Tmax = 0.607	l = −16→16
25133 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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.065P)2 + 4.4856P] where P = (Fo2 + 2Fc2)/3
7532 reflections	(Δ/σ)max = 0.001
510 parameters	Δρmax = 1.08 e Å−3
4 restraints	Δρmin = −0.29 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)
N1	0.6083 (3)	0.38941 (7)	−0.02161 (17)	0.0253 (6)
N2	0.5846 (2)	0.37690 (6)	0.42666 (17)	0.0219 (6)
C1	0.6360 (4)	0.36770 (10)	−0.1171 (2)	0.0396 (10)
C2	0.5318 (5)	0.38991 (13)	−0.2126 (3)	0.0566 (13)
C3	0.3923 (4)	0.39853 (14)	−0.1786 (3)	0.0562 (13)
C4	0.4523 (3)	0.40954 (9)	−0.0600 (2)	0.0329 (8)
C5	0.6297 (3)	0.36064 (8)	0.0717 (2)	0.0256 (7)
C6	0.5944 (3)	0.38106 (8)	0.1656 (2)	0.0262 (7)
C7	0.5387 (3)	0.36176 (8)	0.2373 (2)	0.0237 (7)
C8	0.5085 (3)	0.38700 (7)	0.3248 (2)	0.0229 (7)
C9	0.4040 (3)	0.41905 (8)	0.3069 (2)	0.0271 (7)
C10	0.3852 (3)	0.44096 (8)	0.3946 (2)	0.0300 (8)
C11	0.4688 (3)	0.43054 (8)	0.4977 (2)	0.0279 (8)
C12	0.5685 (3)	0.39775 (8)	0.5118 (2)	0.0243 (7)
C13	0.5056 (3)	0.31700 (8)	0.23996 (19)	0.0240 (7)
C14	0.3774 (3)	0.30343 (9)	0.2686 (2)	0.0302 (8)
C15	0.3474 (4)	0.26157 (10)	0.2725 (2)	0.0375 (9)
C16	0.4406 (4)	0.23209 (9)	0.2476 (2)	0.0376 (9)
C17	0.5687 (4)	0.24541 (9)	0.2205 (2)	0.0346 (8)
C18	0.6013 (3)	0.28713 (8)	0.2174 (2)	0.0292 (8)
C19	0.4090 (5)	0.18638 (10)	0.2523 (3)	0.0536 (13)
Cl1A	1.17727 (7)	0.54478 (2)	0.31560 (5)	0.0301 (2)
Cl2A	0.65597 (7)	0.50251 (2)	−0.11080 (5)	0.0304 (2)
O1A	1.0309 (3)	0.60103 (6)	0.13472 (17)	0.0373 (6)
O2A	0.8198 (2)	0.58421 (6)	−0.05149 (15)	0.0294 (5)
O3A	0.8213 (2)	0.44654 (6)	0.06840 (16)	0.0326 (6)
O4A	1.0396 (2)	0.46331 (6)	0.24478 (15)	0.0292 (5)
C1A	1.0377 (3)	0.53290 (8)	0.1979 (2)	0.0244 (7)
C2A	0.9846 (3)	0.56589 (8)	0.1210 (2)	0.0240 (7)
C3A	0.8602 (3)	0.55558 (8)	0.0146 (2)	0.0239 (7)
C4A	0.8028 (3)	0.51523 (8)	0.00329 (19)	0.0235 (7)
C5A	0.8605 (3)	0.48339 (8)	0.0769 (2)	0.0236 (7)
C6A	0.9862 (3)	0.49402 (8)	0.1777 (2)	0.0234 (7)
Cl1B	0.95280 (7)	0.24300 (2)	0.41301 (6)	0.0322 (2)
Cl2B	0.38936 (10)	0.23353 (2)	0.60046 (9)	0.0526 (3)
O1B	0.7894 (2)	0.16893 (6)	0.45954 (17)	0.0319 (6)
O2B	0.5596 (2)	0.16314 (6)	0.54515 (17)	0.0314 (6)
O3B	0.5501 (2)	0.30750 (6)	0.55902 (17)	0.0323 (6)
O4B	0.7820 (2)	0.31432 (5)	0.47158 (15)	0.0257 (5)
C1B	0.7997 (3)	0.24176 (8)	0.46650 (19)	0.0229 (7)
C2B	0.7414 (3)	0.20213 (8)	0.48159 (19)	0.0236 (7)
C3B	0.6074 (3)	0.20037 (8)	0.5271 (2)	0.0252 (7)
C4B	0.5425 (3)	0.23515 (8)	0.5487 (2)	0.0275 (7)
C5B	0.6020 (3)	0.27584 (8)	0.5340 (2)	0.0244 (7)
C6B	0.7379 (3)	0.27837 (8)	0.48720 (19)	0.0227 (7)
Cl1C	0.18813 (8)	0.00452 (2)	0.81624 (6)	0.0405 (2)
O1C	0.3493 (3)	−0.07006 (7)	0.92826 (19)	0.0422 (7)
O2C	0.3816 (3)	0.07432 (6)	0.92023 (18)	0.0380 (6)
C1C	0.4153 (3)	−0.03683 (8)	0.9587 (2)	0.0279 (8)
C2C	0.3582 (3)	0.00227 (9)	0.9176 (2)	0.0287 (7)
C3C	0.4335 (3)	0.03859 (8)	0.9551 (2)	0.0275 (7)
O1S	0.5299 (3)	0.14776 (7)	0.9411 (2)	0.0366 (8)	0.836 (4)
C1S	0.6758 (5)	0.16296 (13)	1.0010 (4)	0.0446 (14)	0.836 (4)
O2S	0.4348 (14)	−0.1470 (4)	0.9421 (12)	0.0366 (8)	0.164 (4)
C2S	0.298 (2)	−0.1688 (7)	0.940 (2)	0.0446 (14)	0.164 (4)
O1W	0.4911 (3)	0.11809 (7)	0.7256 (2)	0.0500 (8)
H1A	0.60940	0.33800	−0.11770	0.0480*
H1B	0.74380	0.37030	−0.11670	0.0480*
H1C	0.68020	0.41040	−0.00100	0.0300*
H2A	0.57880	0.41590	−0.22770	0.0680*
H2B	0.50750	0.37220	−0.27750	0.0680*
H2C	0.64740	0.35570	0.43770	0.0260*
H3A	0.32570	0.37390	−0.18890	0.0670*
H3B	0.33380	0.42180	−0.22020	0.0670*
H4A	0.46070	0.43990	−0.05030	0.0390*
H4B	0.38390	0.39870	−0.01960	0.0390*
H5A	0.73630	0.35070	0.09410	0.0310*
H5B	0.56230	0.33640	0.04910	0.0310*
H6A	0.61320	0.40990	0.17490	0.0310*
H9A	0.34600	0.42600	0.23580	0.0330*
H10A	0.31460	0.46310	0.38340	0.0360*
H11A	0.45790	0.44570	0.55770	0.0330*
H12A	0.62610	0.38990	0.58230	0.0290*
H14A	0.31060	0.32300	0.28540	0.0360*
H15A	0.26040	0.25300	0.29280	0.0450*
H17A	0.63510	0.22560	0.20370	0.0410*
H18A	0.69050	0.29550	0.19960	0.0350*
H19A	0.33110	0.18210	0.28950	0.0800*
H19B	0.50290	0.17210	0.29140	0.0800*
H19C	0.37270	0.17530	0.17910	0.0800*
H4AA	0.99890	0.44110	0.21770	0.0350*
H2BA	0.60650	0.14510	0.52060	0.0380*
H2CA	0.44580	0.09250	0.94910	0.0460*	0.53 (6)
H1CA	0.40330	−0.08970	0.96060	0.0510*	0.47 (6)
H1S	0.46160	0.16340	0.95050	0.0550*	0.836 (4)
H1S1	0.75540	0.14480	0.98980	0.0670*	0.836 (4)
H1S2	0.68210	0.16350	1.07760	0.0670*	0.836 (4)
H1S3	0.68990	0.19100	0.97680	0.0670*	0.836 (4)
H2S	0.46300	−0.13290	0.99860	0.0550*	0.164 (4)
H2S1	0.21600	−0.14900	0.93630	0.0670*	0.164 (4)
H2S2	0.31540	−0.18550	1.00540	0.0670*	0.164 (4)
H2S3	0.26970	−0.18690	0.87690	0.0670*	0.164 (4)
H1W1	0.509 (6)	0.1352 (12)	0.782 (2)	0.0750*
H1W2	0.526 (6)	0.1329 (12)	0.687 (3)	0.0750*

	U11	U22	U33	U12	U13	U23
N1	0.0281 (11)	0.0271 (10)	0.0237 (10)	−0.0086 (8)	0.0121 (9)	−0.0049 (8)
N2	0.0219 (10)	0.0215 (9)	0.0227 (10)	0.0015 (7)	0.0073 (8)	0.0007 (8)
C1	0.0541 (19)	0.0407 (16)	0.0315 (15)	−0.0100 (14)	0.0243 (14)	−0.0120 (12)
C2	0.078 (3)	0.066 (2)	0.0261 (16)	−0.031 (2)	0.0154 (16)	−0.0012 (15)
C3	0.050 (2)	0.077 (3)	0.0341 (18)	−0.0118 (18)	−0.0001 (15)	0.0200 (17)
C4	0.0323 (14)	0.0280 (13)	0.0394 (15)	−0.0021 (11)	0.0121 (12)	0.0073 (11)
C5	0.0275 (12)	0.0261 (12)	0.0244 (12)	−0.0015 (9)	0.0096 (10)	−0.0012 (9)
C6	0.0305 (13)	0.0247 (12)	0.0245 (12)	−0.0020 (10)	0.0096 (10)	−0.0016 (9)
C7	0.0236 (12)	0.0261 (12)	0.0203 (11)	0.0005 (9)	0.0044 (9)	−0.0019 (9)
C8	0.0239 (12)	0.0241 (11)	0.0215 (12)	−0.0028 (9)	0.0079 (9)	−0.0002 (9)
C9	0.0294 (13)	0.0285 (12)	0.0215 (12)	0.0024 (10)	0.0043 (10)	0.0027 (9)
C10	0.0307 (13)	0.0274 (13)	0.0319 (14)	0.0058 (10)	0.0088 (11)	−0.0001 (10)
C11	0.0284 (13)	0.0302 (13)	0.0265 (13)	−0.0008 (10)	0.0102 (10)	−0.0052 (10)
C12	0.0265 (12)	0.0269 (12)	0.0182 (11)	−0.0021 (9)	0.0043 (9)	−0.0017 (9)
C13	0.0279 (12)	0.0268 (12)	0.0147 (11)	−0.0028 (9)	0.0021 (9)	−0.0002 (9)
C14	0.0309 (13)	0.0359 (14)	0.0217 (12)	−0.0048 (11)	0.0041 (10)	−0.0003 (10)
C15	0.0396 (16)	0.0459 (17)	0.0222 (13)	−0.0172 (13)	0.0013 (11)	0.0051 (11)
C16	0.0557 (19)	0.0297 (14)	0.0180 (12)	−0.0095 (12)	−0.0043 (12)	0.0039 (10)
C17	0.0477 (17)	0.0276 (13)	0.0224 (13)	0.0048 (12)	0.0004 (12)	0.0006 (10)
C18	0.0348 (14)	0.0299 (13)	0.0221 (12)	0.0011 (10)	0.0069 (10)	0.0001 (10)
C19	0.077 (3)	0.0346 (17)	0.0345 (17)	−0.0173 (16)	−0.0076 (16)	0.0073 (13)
Cl1A	0.0304 (3)	0.0339 (3)	0.0225 (3)	−0.0066 (2)	0.0019 (2)	−0.0053 (2)
Cl2A	0.0264 (3)	0.0360 (3)	0.0240 (3)	−0.0046 (2)	−0.0004 (2)	0.0010 (2)
O1A	0.0485 (12)	0.0256 (10)	0.0335 (11)	−0.0067 (8)	0.0051 (9)	−0.0019 (8)
O2A	0.0291 (9)	0.0286 (9)	0.0290 (9)	0.0004 (7)	0.0062 (8)	0.0045 (7)
O3A	0.0330 (10)	0.0255 (9)	0.0342 (10)	−0.0055 (7)	0.0013 (8)	−0.0004 (8)
O4A	0.0310 (10)	0.0265 (9)	0.0253 (9)	−0.0024 (7)	0.0006 (7)	0.0017 (7)
C1A	0.0224 (11)	0.0307 (13)	0.0183 (11)	−0.0014 (9)	0.0031 (9)	−0.0041 (9)
C2A	0.0250 (12)	0.0250 (12)	0.0231 (12)	−0.0016 (9)	0.0088 (10)	−0.0040 (9)
C3A	0.0216 (11)	0.0280 (12)	0.0239 (12)	0.0025 (9)	0.0092 (9)	0.0014 (9)
C4A	0.0190 (11)	0.0301 (12)	0.0198 (11)	−0.0011 (9)	0.0028 (9)	−0.0026 (9)
C5A	0.0218 (11)	0.0265 (12)	0.0230 (12)	−0.0026 (9)	0.0072 (9)	−0.0036 (9)
C6A	0.0219 (11)	0.0284 (12)	0.0199 (11)	0.0007 (9)	0.0062 (9)	0.0003 (9)
Cl1B	0.0295 (3)	0.0312 (3)	0.0419 (4)	0.0047 (2)	0.0199 (3)	0.0024 (3)
Cl2B	0.0561 (5)	0.0320 (4)	0.0915 (7)	0.0010 (3)	0.0562 (5)	0.0018 (4)
O1B	0.0337 (10)	0.0257 (9)	0.0384 (11)	0.0038 (7)	0.0135 (8)	−0.0029 (8)
O2B	0.0343 (10)	0.0238 (9)	0.0406 (11)	−0.0008 (7)	0.0181 (9)	−0.0023 (8)
O3B	0.0374 (10)	0.0271 (9)	0.0386 (11)	0.0042 (8)	0.0209 (9)	0.0011 (8)
O4B	0.0252 (9)	0.0242 (9)	0.0280 (9)	0.0027 (7)	0.0083 (7)	0.0028 (7)
C1B	0.0190 (11)	0.0303 (13)	0.0198 (11)	0.0030 (9)	0.0060 (9)	0.0008 (9)
C2B	0.0217 (11)	0.0278 (12)	0.0191 (11)	0.0050 (9)	0.0025 (9)	−0.0003 (9)
C3B	0.0274 (12)	0.0262 (12)	0.0203 (12)	0.0001 (9)	0.0043 (10)	0.0013 (9)
C4B	0.0256 (12)	0.0321 (13)	0.0278 (13)	0.0007 (10)	0.0125 (10)	0.0010 (10)
C5B	0.0260 (12)	0.0267 (12)	0.0201 (11)	0.0043 (9)	0.0061 (10)	0.0022 (9)
C6B	0.0209 (11)	0.0274 (12)	0.0178 (11)	0.0018 (9)	0.0025 (9)	0.0021 (9)
Cl1C	0.0273 (3)	0.0485 (4)	0.0392 (4)	−0.0011 (3)	−0.0006 (3)	0.0051 (3)
O1C	0.0395 (12)	0.0353 (11)	0.0474 (13)	−0.0103 (9)	0.0055 (10)	0.0020 (9)
O2C	0.0399 (11)	0.0314 (10)	0.0379 (11)	0.0089 (8)	0.0037 (9)	0.0012 (8)
C1C	0.0278 (13)	0.0277 (13)	0.0304 (13)	−0.0035 (10)	0.0118 (11)	−0.0012 (10)
C2C	0.0196 (11)	0.0412 (15)	0.0248 (12)	0.0004 (10)	0.0057 (10)	0.0015 (10)
C3C	0.0291 (13)	0.0266 (12)	0.0296 (13)	0.0037 (10)	0.0131 (11)	0.0040 (10)
O1S	0.0376 (13)	0.0251 (11)	0.0524 (15)	−0.0004 (9)	0.0216 (11)	−0.0056 (10)
C1S	0.037 (2)	0.041 (2)	0.051 (3)	0.0043 (15)	0.0052 (19)	−0.0026 (19)
O2S	0.0376 (13)	0.0251 (11)	0.0524 (15)	−0.0004 (9)	0.0216 (11)	−0.0056 (10)
C2S	0.037 (2)	0.041 (2)	0.051 (3)	0.0043 (15)	0.0052 (19)	−0.0026 (19)
O1W	0.0708 (17)	0.0330 (11)	0.0515 (15)	−0.0025 (11)	0.0260 (13)	0.0042 (10)

Cl1A—C1A	1.731 (3)	C16—C17	1.387 (5)
Cl2A—C4A	1.741 (3)	C16—C19	1.512 (4)
Cl1B—C1B	1.735 (3)	C17—C18	1.386 (4)
Cl2B—C4B	1.722 (3)	C1—H1A	0.9900
Cl1C—C2C	1.729 (3)	C1—H1B	0.9900
O1A—C2A	1.209 (3)	C2—H2A	0.9900
O2A—C3A	1.245 (3)	C2—H2B	0.9900
O3A—C5A	1.242 (3)	C3—H3A	0.9900
O4A—C6A	1.320 (3)	C3—H3B	0.9900
O4A—H4AA	0.8400	C4—H4A	0.9900
O1B—C2B	1.226 (3)	C4—H4B	0.9900
O2B—C3B	1.326 (3)	C5—H5A	0.9900
O3B—C5B	1.213 (3)	C5—H5B	0.9900
O4B—C6B	1.267 (3)	C6—H6A	0.9500
O2B—H2BA	0.8400	C9—H9A	0.9500
O1C—C1C	1.242 (4)	C10—H10A	0.9500
O2C—C3C	1.283 (3)	C11—H11A	0.9500
O1C—H1CA	0.8400	C12—H12A	0.9500
O2C—H2CA	0.8400	C14—H14A	0.9500
O1S—C1S	1.427 (6)	C15—H15A	0.9500
O1S—H1S	0.8400	C17—H17A	0.9500
N1—C5	1.496 (3)	C18—H18A	0.9500
N1—C4	1.519 (4)	C19—H19A	0.9800
N1—C1	1.509 (4)	C19—H19C	0.9800
N2—C8	1.346 (3)	C19—H19B	0.9800
N2—C12	1.339 (3)	C1A—C6A	1.343 (4)
O2S—C2S	1.43 (2)	C1A—C2A	1.448 (4)
N1—H1C	0.9300	C2A—C3A	1.554 (4)
N2—H2C	0.8800	C3A—C4A	1.400 (4)
O2S—H2S	0.8400	C4A—C5A	1.402 (4)
O1W—H1W2	0.82 (5)	C5A—C6A	1.514 (4)
O1W—H1W1	0.90 (3)	C1B—C6B	1.373 (4)
C1—C2	1.512 (5)	C1B—C2B	1.425 (4)
C2—C3	1.494 (6)	C2B—C3B	1.509 (4)
C3—C4	1.521 (5)	C3B—C4B	1.340 (4)
C5—C6	1.501 (4)	C4B—C5B	1.459 (4)
C6—C7	1.338 (4)	C5B—C6B	1.537 (4)
C7—C13	1.483 (4)	C1C—C3Ci	1.512 (4)
C7—C8	1.488 (4)	C1C—C2C	1.414 (4)
C8—C9	1.386 (4)	C2C—C3C	1.379 (4)
C9—C10	1.394 (4)	C1S—H1S1	0.9800
C10—C11	1.380 (4)	C1S—H1S2	0.9800
C11—C12	1.378 (4)	C1S—H1S3	0.9800
C13—C18	1.392 (4)	C2S—H2S3	0.9800
C13—C14	1.401 (4)	C2S—H2S1	0.9800
C14—C15	1.387 (4)	C2S—H2S2	0.9800
C15—C16	1.380 (5)
C6A—O4A—H4AA	109.00	C10—C11—H11A	121.00
C3B—O2B—H2BA	109.00	C11—C12—H12A	120.00
C1C—O1C—H1CA	109.00	N2—C12—H12A	120.00
C3C—O2C—H2CA	109.00	C13—C14—H14A	120.00
C1S—O1S—H1S	109.00	C15—C14—H14A	120.00
C4—N1—C5	115.2 (2)	C16—C15—H15A	119.00
C1—N1—C4	107.1 (2)	C14—C15—H15A	119.00
C1—N1—C5	111.2 (2)	C18—C17—H17A	120.00
C8—N2—C12	122.7 (2)	C16—C17—H17A	119.00
C5—N1—H1C	108.00	C17—C18—H18A	119.00
C4—N1—H1C	108.00	C13—C18—H18A	119.00
C1—N1—H1C	108.00	H19A—C19—H19C	109.00
C12—N2—H2C	119.00	C16—C19—H19B	109.00
C8—N2—H2C	119.00	C16—C19—H19C	110.00
C2S—O2S—H2S	109.00	H19A—C19—H19B	109.00
H1W1—O1W—H1W2	97 (4)	H19B—C19—H19C	109.00
N1—C1—C2	103.7 (3)	C16—C19—H19A	109.00
C1—C2—C3	103.8 (3)	Cl1A—C1A—C2A	117.51 (19)
C2—C3—C4	104.6 (3)	C2A—C1A—C6A	121.8 (2)
N1—C4—C3	105.3 (2)	Cl1A—C1A—C6A	120.6 (2)
N1—C5—C6	112.0 (2)	C1A—C2A—C3A	118.1 (2)
C5—C6—C7	125.0 (2)	O1A—C2A—C3A	118.0 (2)
C6—C7—C13	126.4 (2)	O1A—C2A—C1A	123.9 (2)
C8—C7—C13	115.8 (2)	O2A—C3A—C4A	126.4 (2)
C6—C7—C8	117.8 (2)	C2A—C3A—C4A	116.8 (2)
N2—C8—C9	119.0 (2)	O2A—C3A—C2A	116.7 (2)
C7—C8—C9	123.7 (2)	Cl2A—C4A—C3A	119.03 (19)
N2—C8—C7	117.3 (2)	C3A—C4A—C5A	123.9 (2)
C8—C9—C10	119.1 (2)	Cl2A—C4A—C5A	117.0 (2)
C9—C10—C11	120.3 (2)	O3A—C5A—C6A	115.1 (2)
C10—C11—C12	118.7 (2)	C4A—C5A—C6A	117.8 (2)
N2—C12—C11	120.3 (2)	O3A—C5A—C4A	127.1 (2)
C7—C13—C14	120.4 (2)	O4A—C6A—C5A	116.4 (2)
C7—C13—C18	121.9 (2)	C1A—C6A—C5A	121.3 (2)
C14—C13—C18	117.7 (2)	O4A—C6A—C1A	122.3 (2)
C13—C14—C15	120.4 (3)	C2B—C1B—C6B	123.9 (3)
C14—C15—C16	121.7 (3)	Cl1B—C1B—C6B	119.0 (2)
C15—C16—C19	121.9 (3)	Cl1B—C1B—C2B	117.0 (2)
C17—C16—C19	120.0 (3)	O1B—C2B—C3B	116.4 (2)
C15—C16—C17	118.1 (3)	C1B—C2B—C3B	117.9 (2)
C16—C17—C18	121.0 (3)	O1B—C2B—C1B	125.7 (3)
C13—C18—C17	121.1 (3)	C2B—C3B—C4B	120.7 (2)
N1—C1—H1A	111.00	O2B—C3B—C4B	122.5 (3)
C2—C1—H1A	111.00	O2B—C3B—C2B	116.8 (2)
H1A—C1—H1B	109.00	Cl2B—C4B—C3B	121.1 (2)
N1—C1—H1B	111.00	Cl2B—C4B—C5B	117.1 (2)
C2—C1—H1B	111.00	C3B—C4B—C5B	121.8 (3)
C3—C2—H2A	111.00	C4B—C5B—C6B	118.4 (2)
C1—C2—H2B	111.00	O3B—C5B—C6B	119.1 (2)
C1—C2—H2A	111.00	O3B—C5B—C4B	122.5 (3)
H2A—C2—H2B	109.00	C1B—C6B—C5B	117.3 (2)
C3—C2—H2B	111.00	O4B—C6B—C5B	116.4 (2)
C4—C3—H3B	111.00	O4B—C6B—C1B	126.4 (3)
H3A—C3—H3B	109.00	O1C—C1C—C2C	124.2 (3)
C2—C3—H3A	111.00	C2C—C1C—C3Ci	118.3 (2)
C4—C3—H3A	111.00	O1C—C1C—C3Ci	117.5 (2)
C2—C3—H3B	111.00	C1C—C2C—C3C	122.4 (2)
C3—C4—H4B	111.00	Cl1C—C2C—C3C	118.9 (2)
C3—C4—H4A	111.00	Cl1C—C2C—C1C	118.7 (2)
N1—C4—H4A	111.00	C1Ci—C3C—C2C	119.2 (2)
H4A—C4—H4B	109.00	O2C—C3C—C2C	123.2 (3)
N1—C4—H4B	111.00	O2C—C3C—C1Ci	117.6 (2)
H5A—C5—H5B	108.00	O1S—C1S—H1S3	109.00
C6—C5—H5A	109.00	O1S—C1S—H1S1	109.00
N1—C5—H5B	109.00	O1S—C1S—H1S2	109.00
C6—C5—H5B	109.00	H1S2—C1S—H1S3	109.00
N1—C5—H5A	109.00	H1S1—C1S—H1S2	109.00
C7—C6—H6A	117.00	H1S1—C1S—H1S3	110.00
C5—C6—H6A	118.00	O2S—C2S—H2S2	109.00
C10—C9—H9A	120.00	O2S—C2S—H2S3	109.00
C8—C9—H9A	120.00	O2S—C2S—H2S1	110.00
C11—C10—H10A	120.00	H2S1—C2S—H2S3	110.00
C9—C10—H10A	120.00	H2S2—C2S—H2S3	109.00
C12—C11—H11A	121.00	H2S1—C2S—H2S2	110.00
C4—N1—C1—C2	22.8 (3)	C1A—C2A—C3A—C4A	3.1 (4)
C5—N1—C1—C2	149.4 (3)	O2A—C3A—C4A—Cl2A	−2.3 (4)
C1—N1—C4—C3	0.4 (3)	O2A—C3A—C4A—C5A	175.1 (3)
C5—N1—C4—C3	−123.9 (3)	C2A—C3A—C4A—Cl2A	176.54 (19)
C1—N1—C5—C6	−176.9 (2)	C2A—C3A—C4A—C5A	−6.1 (4)
C4—N1—C5—C6	−54.8 (3)	Cl2A—C4A—C5A—O3A	2.2 (4)
C8—N2—C12—C11	1.3 (4)	Cl2A—C4A—C5A—C6A	−178.9 (2)
C12—N2—C8—C7	179.0 (2)	C3A—C4A—C5A—O3A	−175.2 (3)
C12—N2—C8—C9	−3.0 (4)	C3A—C4A—C5A—C6A	3.7 (4)
N1—C1—C2—C3	−37.7 (4)	O3A—C5A—C6A—O4A	−0.1 (4)
C1—C2—C3—C4	38.2 (4)	O3A—C5A—C6A—C1A	−178.9 (3)
C2—C3—C4—N1	−23.8 (4)	C4A—C5A—C6A—O4A	−179.1 (2)
N1—C5—C6—C7	149.1 (3)	C4A—C5A—C6A—C1A	2.1 (4)
C5—C6—C7—C8	−179.2 (2)	Cl1B—C1B—C2B—O1B	−0.4 (4)
C5—C6—C7—C13	1.9 (5)	Cl1B—C1B—C2B—C3B	−179.48 (18)
C13—C7—C8—C9	−118.6 (3)	C6B—C1B—C2B—O1B	176.6 (3)
C6—C7—C13—C14	−142.1 (3)	C6B—C1B—C2B—C3B	−2.5 (4)
C6—C7—C13—C18	39.7 (4)	Cl1B—C1B—C6B—O4B	−0.4 (4)
C8—C7—C13—C14	39.0 (3)	Cl1B—C1B—C6B—C5B	179.70 (18)
C8—C7—C13—C18	−139.2 (3)	C2B—C1B—C6B—O4B	−177.3 (2)
C6—C7—C8—C9	62.4 (4)	C2B—C1B—C6B—C5B	2.7 (4)
C13—C7—C8—N2	59.3 (3)	O1B—C2B—C3B—O2B	3.9 (3)
C6—C7—C8—N2	−119.7 (3)	O1B—C2B—C3B—C4B	−176.7 (2)
N2—C8—C9—C10	2.6 (4)	C1B—C2B—C3B—O2B	−176.9 (2)
C7—C8—C9—C10	−179.5 (3)	C1B—C2B—C3B—C4B	2.4 (4)
C8—C9—C10—C11	−0.5 (4)	O2B—C3B—C4B—Cl2B	−0.8 (4)
C9—C10—C11—C12	−1.1 (4)	O2B—C3B—C4B—C5B	176.5 (2)
C10—C11—C12—N2	0.8 (4)	C2B—C3B—C4B—Cl2B	179.9 (2)
C7—C13—C14—C15	−179.2 (2)	C2B—C3B—C4B—C5B	−2.8 (4)
C18—C13—C14—C15	−0.9 (4)	Cl2B—C4B—C5B—O3B	1.8 (4)
C7—C13—C18—C17	179.9 (2)	Cl2B—C4B—C5B—C6B	−179.56 (18)
C14—C13—C18—C17	1.6 (4)	C3B—C4B—C5B—O3B	−175.6 (3)
C13—C14—C15—C16	−0.7 (4)	C3B—C4B—C5B—C6B	3.0 (4)
C14—C15—C16—C17	1.4 (4)	O3B—C5B—C6B—O4B	−4.1 (4)
C14—C15—C16—C19	179.7 (3)	O3B—C5B—C6B—C1B	175.8 (2)
C15—C16—C17—C18	−0.7 (4)	C4B—C5B—C6B—O4B	177.2 (2)
C19—C16—C17—C18	−178.9 (3)	C4B—C5B—C6B—C1B	−2.9 (3)
C16—C17—C18—C13	−0.9 (4)	O1C—C1C—C2C—Cl1C	−1.6 (4)
Cl1A—C1A—C2A—O1A	−0.7 (4)	O1C—C1C—C2C—C3C	178.6 (3)
Cl1A—C1A—C2A—C3A	179.5 (2)	C3Ci—C1C—C2C—Cl1C	178.13 (19)
C6A—C1A—C2A—O1A	−177.9 (3)	C3Ci—C1C—C2C—C3C	−1.6 (4)
C6A—C1A—C2A—C3A	2.3 (4)	O1C—C1C—C3Ci—O2Ci	1.2 (4)
Cl1A—C1A—C6A—O4A	−0.8 (4)	O1C—C1C—C3Ci—C2Ci	−178.7 (3)
Cl1A—C1A—C6A—C5A	177.9 (2)	C2C—C1C—C3Ci—O2Ci	−178.6 (3)
C2A—C1A—C6A—O4A	176.4 (3)	C2C—C1C—C3Ci—C2Ci	1.5 (4)
C2A—C1A—C6A—C5A	−4.9 (4)	Cl1C—C2C—C3C—O2C	1.8 (4)
O1A—C2A—C3A—O2A	2.3 (4)	Cl1C—C2C—C3C—C1Ci	−178.1 (2)
O1A—C2A—C3A—C4A	−176.7 (3)	C1C—C2C—C3C—O2C	−178.5 (3)
C1A—C2A—C3A—O2A	−178.0 (2)	C1C—C2C—C3C—C1Ci	1.6 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O4A—H4AA···O3A	0.84	2.15	2.629 (3)	116
O4A—H4AA···O1Wii	0.84	1.92	2.672 (3)	148
N1—H1C···O3A	0.93	1.78	2.699 (3)	167
O2B—H2BA···O1B	0.84	2.19	2.655 (3)	115
O2B—H2BA···O1Aiii	0.84	2.50	3.012 (3)	121
O2B—H2BA···O2Aiii	0.84	2.08	2.776 (3)	139
N2—H2C···O3B	0.88	2.55	2.900 (3)	104
N2—H2C···O4B	0.88	1.79	2.667 (3)	175
O2C—H2CA···O1Ci	0.84	2.21	2.680 (4)	116
O1W—H1W1···O1S	0.90 (3)	2.06 (3)	2.882 (3)	152 (4)
O1W—H1W2···O2B	0.82 (5)	2.18 (4)	2.976 (3)	162 (4)
C1—H1B···O1Aiv	0.99	2.34	3.286 (5)	160
C3—H3A···O1Bv	0.99	2.47	3.138 (5)	124
C4—H4B···O2Avi	0.99	2.37	3.229 (3)	144
C4—H4B···O1Bv	0.99	2.34	2.994 (3)	123
C5—H5B···O1Bv	0.99	2.44	3.186 (3)	132
C9—H9A···Cl2Avi	0.95	2.82	3.525 (3)	131
C9—H9A···O2Avi	0.95	2.46	3.363 (3)	158
C18—H18A···Cl2Bii	0.95	2.68	3.467 (3)	140
C19—H19B···O1Aiii	0.98	2.55	3.102 (4)	116

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4A—H4AA⋯O3A	0.84	2.15	2.629 (3)	116
O4A—H4AA⋯O1Wi	0.84	1.92	2.672 (3)	148
N1—H1C⋯O3A	0.93	1.78	2.699 (3)	167
O2B—H2BA⋯O1B	0.84	2.19	2.655 (3)	115
O2B—H2BA⋯O1Aii	0.84	2.50	3.012 (3)	121
O2B—H2BA⋯O2Aii	0.84	2.08	2.776 (3)	139
N2—H2C⋯O3B	0.88	2.55	2.900 (3)	104
N2—H2C⋯O4B	0.88	1.79	2.667 (3)	175
O2C—H2CA⋯O1Ciii	0.84	2.21	2.680 (4)	116
O1W—H1W1⋯O1S	0.90 (3)	2.06 (3)	2.882 (3)	152 (4)
O1W—H1W2⋯O2B	0.82 (5)	2.18 (4)	2.976 (3)	162 (4)
C1—H1B⋯O1Aiv	0.99	2.34	3.286 (5)	160
C3—H3A⋯O1Bv	0.99	2.47	3.138 (5)	124
C4—H4B⋯O2Avi	0.99	2.37	3.229 (3)	144
C4—H4B⋯O1Bv	0.99	2.34	2.994 (3)	123
C5—H5B⋯O1Bv	0.99	2.44	3.186 (3)	132
C9—H9A⋯Cl2Avi	0.95	2.82	3.525 (3)	131
C9—H9A⋯O2Avi	0.95	2.46	3.363 (3)	158
C18—H18A⋯Cl2Bi	0.95	2.68	3.467 (3)	140
C19—H19B⋯O1Aii	0.98	2.55	3.102 (4)	116

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