4-[Bis(4-fluoro-phen-yl)meth-yl]piperazin-1-ium bis-(trichloro-acetate) 0.4-hydrate.

The title compound, C(17)H(20)F(2)N(2) (2+)·2C(2)Cl(3)O(2) (-)·0.4H(2)O, has twofold protonated N atoms. The trichloro-acetate anions each show one disordered Cl atom with site occupation factors of 0.945 (7):0.055 (7) 0.945 (8):0.055 (8). In the crystal, N-H⋯O, O(water)-H⋯O and O(water)-H⋯F inter-actions connect the components into a three-dimensional network.

Related literature

For the biological activity of piperazines, see: Bogatcheva et al. (2006 ▶); Brockunier et al. (2004 ▶). For a review pharmacological and toxicological information for piperazine derivatives, see: Elliott, (2011 ▶). For related structures, see: Betz et al. (2011 ▶, 2011a ▶); Perpétuo & Janczak (2006 ▶). For graph-set analysis of hydrogen bonds, see: Bernstein et al. (1995 ▶); Etter et al. (1990 ▶). For puckering analysis, see: Cremer & Pople (1975 ▶).

Experimental

Crystal data

C17H20F2N2 2+·2C2Cl3O2 −·0.4H2O

M = 622.30

Monoclinic,

a = 8.8101 (7) Å

b = 33.555 (3) Å

c = 9.4453 (7) Å

β = 108.723 (2)°

V = 2644.5 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.70 mm−1

T = 130 K

0.43 × 0.25 × 0.23 mm

Data collection

Bruker SMART APEX diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ▶) T min = 0.754, T max = 0.856

25025 measured reflections

6309 independent reflections

5475 reflections with I > 2σ(I)

R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.094

S = 1.12

6309 reflections

343 parameters

5 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.33 e Å−3

Data collection: SMART (Bruker, 2002 ▶); cell refinement: SAINT (Bruker, 2002 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and local programs.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812009282/zj2061sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812009282/zj2061Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812009282/zj2061Isup3.cml

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

C17H20F2N22+·2C2Cl3O2−·0.4H2O	F(000) = 1264
Mr = 622.30	Dx = 1.563 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6364 reflections
a = 8.8101 (7) Å	θ = 2.4–28.1°
b = 33.555 (3) Å	µ = 0.70 mm−1
c = 9.4453 (7) Å	T = 130 K
β = 108.723 (2)°	Block, colourless
V = 2644.5 (3) Å3	0.43 × 0.25 × 0.23 mm
Z = 4

Bruker SMART APEX diffractometer	6309 independent reflections
Radiation source: sealed tube	5475 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
φ and ω scans	θmax = 27.9°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −11→11
Tmin = 0.754, Tmax = 0.856	k = −44→35
25025 measured reflections	l = −12→12

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.094	H atoms treated by a mixture of independent and constrained refinement
S = 1.12	w = 1/[σ2(Fo2) + (0.0376P)2 + 1.238P] where P = (Fo2 + 2Fc2)/3
6309 reflections	(Δ/σ)max < 0.001
343 parameters	Δρmax = 0.44 e Å−3
5 restraints	Δρmin = −0.33 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	0.42896 (7)	0.08738 (2)	0.57017 (6)	0.04709 (17)
Cl2	0.73291 (7)	0.122760 (16)	0.73174 (6)	0.03824 (14)
Cl31	0.7180 (2)	0.039699 (19)	0.66377 (16)	0.0288 (3)	0.945 (7)
Cl32	0.655 (3)	0.0375 (3)	0.625 (2)	0.030 (3)*	0.055 (7)
O1	0.57723 (16)	0.09907 (4)	0.94355 (15)	0.0257 (3)
O2	0.51880 (15)	0.03603 (4)	0.86531 (14)	0.0218 (3)
C1	0.6146 (2)	0.07955 (6)	0.71377 (19)	0.0210 (4)
C2	0.5687 (2)	0.07066 (5)	0.85888 (19)	0.0183 (3)
Cl4	1.04646 (6)	0.05481 (2)	0.43723 (6)	0.04426 (16)
Cl51	0.7926 (3)	0.11414 (3)	0.3445 (2)	0.0353 (4)	0.945 (9)
Cl52	0.852 (3)	0.1118 (3)	0.385 (2)	0.030 (4)*	0.055 (9)
Cl6	0.72048 (5)	0.031251 (14)	0.28437 (5)	0.02344 (11)
O3	0.97280 (16)	0.10468 (4)	0.13520 (15)	0.0243 (3)
O4	0.89212 (15)	0.04212 (4)	0.06973 (14)	0.0210 (3)
C3	0.8647 (2)	0.06867 (6)	0.29606 (19)	0.0209 (4)
C4	0.9108 (2)	0.07214 (5)	0.14910 (19)	0.0175 (3)
F1	0.47404 (19)	0.21857 (4)	0.64013 (15)	0.0531 (4)
F2	−0.14523 (17)	0.26032 (4)	−0.34231 (15)	0.0443 (3)
N1	0.22837 (17)	0.11350 (4)	0.04351 (15)	0.0163 (3)
H1B	0.1356	0.1125	0.0701	0.020*
N2	0.26897 (17)	0.03018 (4)	−0.02096 (16)	0.0176 (3)
H2A	0.2369	0.0040	−0.0286	0.021*
H2B	0.3617	0.0318	−0.0457	0.021*
C10	0.2875 (2)	0.15637 (5)	0.05572 (19)	0.0193 (4)
H1A	0.3867	0.1565	0.0260	0.023*
C11	0.3345 (2)	0.17165 (5)	0.2157 (2)	0.0224 (4)
C12	0.2363 (3)	0.16824 (6)	0.3048 (2)	0.0265 (4)
H12A	0.1357	0.1551	0.2669	0.032*
C13	0.2841 (3)	0.18384 (6)	0.4487 (2)	0.0328 (5)
H13A	0.2180	0.1812	0.5103	0.039*
C14	0.4278 (3)	0.20306 (6)	0.4998 (2)	0.0353 (5)
C15	0.5268 (3)	0.20753 (7)	0.4159 (2)	0.0399 (5)
H15A	0.6257	0.2213	0.4543	0.048*
C16	0.4798 (3)	0.19138 (6)	0.2723 (2)	0.0325 (5)
H16A	0.5480	0.1939	0.2127	0.039*
C21	0.1666 (2)	0.18308 (5)	−0.05342 (19)	0.0205 (4)
C22	0.0095 (2)	0.18688 (6)	−0.0532 (2)	0.0242 (4)
H22A	−0.0256	0.1716	0.0151	0.029*
C23	−0.0966 (2)	0.21262 (6)	−0.1512 (2)	0.0282 (4)
H23A	−0.2040	0.2152	−0.1513	0.034*
C24	−0.0419 (3)	0.23440 (6)	−0.2483 (2)	0.0294 (4)
C25	0.1114 (3)	0.23131 (6)	−0.2544 (2)	0.0321 (5)
H25A	0.1449	0.2466	−0.3237	0.039*
C26	0.2160 (2)	0.20519 (6)	−0.1560 (2)	0.0270 (4)
H26A	0.3223	0.2023	−0.1586	0.032*
C32	0.1905 (2)	0.09844 (5)	−0.11400 (18)	0.0185 (3)
H32A	0.2858	0.1017	−0.1468	0.022*
H32B	0.1023	0.1145	−0.1812	0.022*
C33	0.1419 (2)	0.05501 (5)	−0.12607 (19)	0.0192 (4)
H33A	0.0407	0.0520	−0.1028	0.023*
H33B	0.1230	0.0457	−0.2297	0.023*
C35	0.3000 (2)	0.04431 (5)	0.13512 (19)	0.0179 (3)
H35A	0.3842	0.0276	0.2045	0.022*
H35B	0.2012	0.0418	0.1628	0.022*
C36	0.3534 (2)	0.08726 (5)	0.14877 (18)	0.0175 (3)
H36A	0.3733	0.0964	0.2528	0.021*
H36B	0.4551	0.0895	0.1258	0.021*
O100	0.6383 (5)	0.17843 (13)	0.9984 (5)	0.0411 (15)	0.398 (5)
H101	0.636 (11)	0.1549 (10)	0.968 (10)	0.10 (3)*	0.398 (5)
H102	0.720 (7)	0.181 (3)	1.075 (6)	0.10 (3)*	0.398 (5)

	U11	U22	U33	U12	U13	U23
Cl1	0.0302 (3)	0.0767 (5)	0.0258 (3)	0.0066 (3)	−0.0029 (2)	0.0160 (3)
Cl2	0.0497 (3)	0.0321 (3)	0.0420 (3)	−0.0160 (2)	0.0275 (3)	−0.0024 (2)
Cl31	0.0361 (8)	0.0300 (3)	0.0275 (5)	0.0028 (3)	0.0201 (5)	0.0011 (2)
O1	0.0276 (7)	0.0258 (7)	0.0278 (7)	−0.0033 (6)	0.0146 (6)	−0.0041 (6)
O2	0.0204 (6)	0.0216 (7)	0.0260 (7)	−0.0008 (5)	0.0112 (5)	0.0021 (5)
C1	0.0198 (9)	0.0241 (9)	0.0185 (8)	−0.0009 (7)	0.0054 (7)	0.0033 (7)
C2	0.0113 (8)	0.0248 (9)	0.0187 (8)	0.0028 (7)	0.0046 (6)	0.0042 (7)
Cl4	0.0244 (3)	0.0773 (5)	0.0237 (3)	−0.0059 (3)	−0.0027 (2)	0.0090 (3)
Cl51	0.0431 (9)	0.0314 (3)	0.0402 (7)	−0.0065 (4)	0.0258 (7)	−0.0164 (3)
Cl6	0.0226 (2)	0.0282 (2)	0.0228 (2)	−0.00551 (18)	0.01187 (17)	−0.00174 (17)
O3	0.0247 (7)	0.0210 (7)	0.0316 (7)	−0.0053 (5)	0.0150 (6)	−0.0038 (5)
O4	0.0218 (6)	0.0214 (7)	0.0223 (6)	−0.0044 (5)	0.0105 (5)	−0.0046 (5)
C3	0.0182 (9)	0.0271 (10)	0.0181 (8)	−0.0036 (7)	0.0066 (7)	−0.0044 (7)
C4	0.0114 (8)	0.0224 (9)	0.0190 (8)	0.0009 (6)	0.0054 (6)	0.0009 (7)
F1	0.0701 (10)	0.0504 (9)	0.0271 (7)	−0.0105 (7)	−0.0008 (7)	−0.0165 (6)
F2	0.0456 (8)	0.0331 (7)	0.0419 (8)	0.0057 (6)	−0.0030 (6)	0.0182 (6)
N1	0.0174 (7)	0.0155 (7)	0.0165 (7)	−0.0002 (6)	0.0064 (6)	0.0003 (5)
N2	0.0179 (7)	0.0153 (7)	0.0208 (7)	−0.0008 (6)	0.0079 (6)	−0.0005 (6)
C10	0.0200 (9)	0.0169 (9)	0.0204 (8)	−0.0036 (7)	0.0056 (7)	0.0006 (7)
C11	0.0269 (10)	0.0155 (9)	0.0202 (9)	−0.0002 (7)	0.0010 (7)	0.0013 (7)
C12	0.0321 (11)	0.0215 (10)	0.0237 (9)	−0.0024 (8)	0.0056 (8)	−0.0034 (7)
C13	0.0456 (13)	0.0256 (11)	0.0258 (10)	0.0017 (9)	0.0093 (9)	−0.0031 (8)
C14	0.0500 (14)	0.0236 (10)	0.0224 (10)	−0.0005 (9)	−0.0022 (9)	−0.0050 (8)
C15	0.0400 (13)	0.0356 (13)	0.0322 (11)	−0.0140 (10)	−0.0048 (10)	−0.0046 (9)
C16	0.0317 (11)	0.0310 (11)	0.0302 (11)	−0.0079 (9)	0.0036 (9)	0.0012 (8)
C21	0.0254 (9)	0.0156 (9)	0.0185 (8)	−0.0034 (7)	0.0042 (7)	−0.0020 (7)
C22	0.0277 (10)	0.0205 (9)	0.0238 (9)	0.0005 (8)	0.0072 (8)	0.0033 (7)
C23	0.0282 (10)	0.0241 (10)	0.0288 (10)	0.0016 (8)	0.0042 (8)	0.0002 (8)
C24	0.0374 (12)	0.0177 (9)	0.0244 (9)	0.0003 (8)	−0.0023 (8)	0.0039 (7)
C25	0.0421 (12)	0.0237 (10)	0.0282 (10)	−0.0063 (9)	0.0082 (9)	0.0074 (8)
C26	0.0306 (11)	0.0232 (10)	0.0257 (10)	−0.0050 (8)	0.0068 (8)	0.0029 (8)
C32	0.0201 (9)	0.0208 (9)	0.0144 (8)	0.0016 (7)	0.0053 (7)	−0.0001 (6)
C33	0.0171 (8)	0.0212 (9)	0.0184 (8)	0.0002 (7)	0.0047 (7)	−0.0010 (7)
C35	0.0179 (8)	0.0189 (9)	0.0183 (8)	0.0011 (7)	0.0076 (7)	0.0006 (6)
C36	0.0176 (8)	0.0183 (9)	0.0158 (8)	0.0019 (7)	0.0041 (7)	0.0011 (6)
O100	0.045 (3)	0.034 (2)	0.051 (3)	−0.0121 (19)	0.025 (2)	−0.0149 (19)

Cl1—C1	1.7777 (19)	C12—C13	1.390 (3)
Cl2—C1	1.7616 (19)	C12—H12A	0.9500
Cl31—Cl32	0.56 (3)	C13—C14	1.364 (3)
Cl31—C1	1.766 (2)	C13—H13A	0.9500
Cl32—C1	1.733 (11)	C14—C15	1.362 (3)
O1—C2	1.231 (2)	C15—C16	1.394 (3)
O2—C2	1.251 (2)	C15—H15A	0.9500
C1—C2	1.577 (2)	C16—H16A	0.9500
Cl4—C3	1.7852 (19)	C21—C22	1.391 (3)
Cl51—Cl52	0.55 (3)	C21—C26	1.396 (3)
Cl51—C3	1.768 (2)	C22—C23	1.386 (3)
Cl52—C3	1.696 (11)	C22—H22A	0.9500
Cl6—C3	1.7646 (19)	C23—C24	1.375 (3)
O3—C4	1.246 (2)	C23—H23A	0.9500
O4—C4	1.235 (2)	C24—C25	1.373 (3)
C3—C4	1.571 (2)	C25—C26	1.389 (3)
F1—C14	1.359 (2)	C25—H25A	0.9500
F2—C24	1.362 (2)	C26—H26A	0.9500
N1—C32	1.504 (2)	C32—C33	1.513 (2)
N1—C36	1.508 (2)	C32—H32A	0.9900
N1—C10	1.522 (2)	C32—H32B	0.9900
N1—H1B	0.9300	C33—H33A	0.9900
N2—C35	1.488 (2)	C33—H33B	0.9900
N2—C33	1.490 (2)	C35—C36	1.508 (2)
N2—H2A	0.9200	C35—H35A	0.9900
N2—H2B	0.9200	C35—H35B	0.9900
C10—C21	1.515 (2)	C36—H36A	0.9900
C10—C11	1.522 (2)	C36—H36B	0.9900
C10—H1A	1.0000	O100—H101	0.840 (10)
C11—C16	1.387 (3)	O100—H102	0.839 (10)
C11—C12	1.392 (3)
Cl32—Cl31—C1	77.4 (11)	C14—C13—H13A	120.7
Cl31—Cl32—C1	84.0 (13)	C12—C13—H13A	120.7
C2—C1—Cl32	114.5 (4)	F1—C14—C15	118.6 (2)
C2—C1—Cl2	112.39 (12)	F1—C14—C13	118.6 (2)
Cl32—C1—Cl2	120.7 (7)	C15—C14—C13	122.8 (2)
C2—C1—Cl31	112.80 (12)	C14—C15—C16	118.5 (2)
Cl32—C1—Cl31	18.5 (9)	C14—C15—H15A	120.7
Cl2—C1—Cl31	108.00 (11)	C16—C15—H15A	120.7
C2—C1—Cl1	105.13 (12)	C11—C16—C15	120.7 (2)
Cl32—C1—Cl1	91.9 (10)	C11—C16—H16A	119.7
Cl2—C1—Cl1	108.84 (10)	C15—C16—H16A	119.7
Cl31—C1—Cl1	109.59 (12)	C22—C21—C26	118.96 (17)
O1—C2—O2	129.59 (16)	C22—C21—C10	122.39 (16)
O1—C2—C1	116.02 (16)	C26—C21—C10	118.64 (17)
O2—C2—C1	114.21 (15)	C23—C22—C21	120.93 (18)
Cl52—Cl51—C3	73.5 (12)	C23—C22—H22A	119.5
Cl51—Cl52—C3	88.5 (16)	C21—C22—H22A	119.5
C4—C3—Cl52	116.9 (5)	C24—C23—C22	118.10 (19)
C4—C3—Cl6	112.51 (12)	C24—C23—H23A	120.9
Cl52—C3—Cl6	118.4 (7)	C22—C23—H23A	120.9
C4—C3—Cl51	112.38 (13)	F2—C24—C25	118.79 (18)
Cl52—C3—Cl51	18.0 (9)	F2—C24—C23	118.0 (2)
Cl6—C3—Cl51	108.59 (11)	C25—C24—C23	123.19 (18)
C4—C3—Cl4	104.78 (12)	C24—C25—C26	117.99 (19)
Cl52—C3—Cl4	92.2 (10)	C24—C25—H25A	121.0
Cl6—C3—Cl4	108.46 (10)	C26—C25—H25A	121.0
Cl51—C3—Cl4	110.00 (13)	C25—C26—C21	120.81 (19)
O4—C4—O3	128.92 (16)	C25—C26—H26A	119.6
O4—C4—C3	117.01 (15)	C21—C26—H26A	119.6
O3—C4—C3	113.85 (15)	N1—C32—C33	111.45 (14)
C32—N1—C36	109.84 (13)	N1—C32—H32A	109.3
C32—N1—C10	110.76 (13)	C33—C32—H32A	109.3
C36—N1—C10	110.02 (13)	N1—C32—H32B	109.3
C32—N1—H1B	108.7	C33—C32—H32B	109.3
C36—N1—H1B	108.7	H32A—C32—H32B	108.0
C10—N1—H1B	108.7	N2—C33—C32	110.77 (14)
C35—N2—C33	110.00 (13)	N2—C33—H33A	109.5
C35—N2—H2A	109.7	C32—C33—H33A	109.5
C33—N2—H2A	109.7	N2—C33—H33B	109.5
C35—N2—H2B	109.7	C32—C33—H33B	109.5
C33—N2—H2B	109.7	H33A—C33—H33B	108.1
H2A—N2—H2B	108.2	N2—C35—C36	110.01 (13)
C21—C10—N1	111.04 (14)	N2—C35—H35A	109.7
C21—C10—C11	112.61 (15)	C36—C35—H35A	109.7
N1—C10—C11	111.79 (14)	N2—C35—H35B	109.7
C21—C10—H1A	107.0	C36—C35—H35B	109.7
N1—C10—H1A	107.0	H35A—C35—H35B	108.2
C11—C10—H1A	107.0	N1—C36—C35	111.11 (14)
C16—C11—C12	118.84 (18)	N1—C36—H36A	109.4
C16—C11—C10	117.85 (18)	C35—C36—H36A	109.4
C12—C11—C10	123.26 (17)	N1—C36—H36B	109.4
C13—C12—C11	120.55 (19)	C35—C36—H36B	109.4
C13—C12—H12A	119.7	H36A—C36—H36B	108.0
C11—C12—H12A	119.7	H101—O100—H102	107 (7)
C14—C13—C12	118.6 (2)
Cl31—Cl32—C1—C2	−88.9 (13)	C21—C10—C11—C12	75.9 (2)
Cl31—Cl32—C1—Cl2	50.3 (14)	N1—C10—C11—C12	−50.0 (2)
Cl31—Cl32—C1—Cl1	163.5 (12)	C16—C11—C12—C13	−0.9 (3)
Cl32—Cl31—C1—C2	99.2 (13)	C10—C11—C12—C13	−178.09 (18)
Cl32—Cl31—C1—Cl2	−135.9 (13)	C11—C12—C13—C14	1.0 (3)
Cl32—Cl31—C1—Cl1	−17.5 (13)	C12—C13—C14—F1	179.54 (19)
Cl32—C1—C2—O1	163.1 (11)	C12—C13—C14—C15	−0.2 (3)
Cl2—C1—C2—O1	20.5 (2)	F1—C14—C15—C16	179.6 (2)
Cl31—C1—C2—O1	142.94 (16)	C13—C14—C15—C16	−0.7 (4)
Cl1—C1—C2—O1	−97.70 (16)	C12—C11—C16—C15	0.0 (3)
Cl32—C1—C2—O2	−21.3 (11)	C10—C11—C16—C15	177.33 (19)
Cl2—C1—C2—O2	−163.85 (13)	C14—C15—C16—C11	0.8 (3)
Cl31—C1—C2—O2	−41.5 (2)	N1—C10—C21—C22	57.6 (2)
Cl1—C1—C2—O2	77.91 (16)	C11—C10—C21—C22	−68.6 (2)
Cl51—Cl52—C3—C4	79.5 (17)	N1—C10—C21—C26	−123.58 (17)
Cl51—Cl52—C3—Cl6	−60.3 (15)	C11—C10—C21—C26	110.19 (19)
Cl51—Cl52—C3—Cl4	−172.7 (14)	C26—C21—C22—C23	−1.0 (3)
Cl52—Cl51—C3—C4	−108.6 (16)	C10—C21—C22—C23	177.77 (17)
Cl52—Cl51—C3—Cl6	126.3 (15)	C21—C22—C23—C24	−0.2 (3)
Cl52—Cl51—C3—Cl4	7.8 (15)	C22—C23—C24—F2	−178.57 (17)
Cl52—C3—C4—O4	−167.2 (11)	C22—C23—C24—C25	1.2 (3)
Cl6—C3—C4—O4	−25.1 (2)	F2—C24—C25—C26	178.97 (18)
Cl51—C3—C4—O4	−148.05 (16)	C23—C24—C25—C26	−0.8 (3)
Cl4—C3—C4—O4	92.53 (16)	C24—C25—C26—C21	−0.6 (3)
Cl52—C3—C4—O3	17.7 (12)	C22—C21—C26—C25	1.4 (3)
Cl6—C3—C4—O3	159.81 (13)	C10—C21—C26—C25	−177.41 (17)
Cl51—C3—C4—O3	36.9 (2)	C36—N1—C32—C33	54.54 (18)
Cl4—C3—C4—O3	−82.56 (16)	C10—N1—C32—C33	176.28 (14)
C32—N1—C10—C21	56.15 (18)	C35—N2—C33—C32	58.39 (18)
C36—N1—C10—C21	177.78 (14)	N1—C32—C33—N2	−56.38 (18)
C32—N1—C10—C11	−177.16 (14)	C33—N2—C35—C36	−59.54 (17)
C36—N1—C10—C11	−55.53 (18)	C32—N1—C36—C35	−55.92 (17)
C21—C10—C11—C16	−101.3 (2)	C10—N1—C36—C35	−178.09 (13)
N1—C10—C11—C16	132.84 (18)	N2—C35—C36—N1	58.83 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O3i	0.93	1.75	2.6756 (19)	172
N2—H2A···O4ii	0.92	1.88	2.7735 (19)	162
N2—H2B···O2iii	0.92	1.84	2.7487 (19)	168
O100—H102···F2iv	0.84 (1)	2.32 (8)	2.878 (4)	125 (8)
O100—H101···O1	0.84 (1)	1.94 (4)	2.733 (4)	158 (9)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O3i	0.93	1.75	2.6756 (19)	172
N2—H2A⋯O4ii	0.92	1.88	2.7735 (19)	162
N2—H2B⋯O2iii	0.92	1.84	2.7487 (19)	168
O100—H102⋯F2iv	0.84 (1)	2.32 (8)	2.878 (4)	125 (8)
O100—H101⋯O1	0.84 (1)	1.94 (4)	2.733 (4)	158 (9)

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