Poly[[μ-chlorido-μ-[2-(2,4-di-fluoro-phen-yl)-1,3-bis-(1,2,4-triazol-1-yl)propan-2-ol-κ(2) N (4):N (4')]-zinc] chloride dihydrate].

The title compound, {[ZnCl(C13H12F2N6O)2]Cl·2H2O} n , is a two-dimensional coordination polymer. The Zn(II) atom is six-coordinated by four N atoms from four 2-(2,4-di-fluoro-phen-yl)-1,3-bis-(1,2,4-triazol-1-yl)propan-2-ol (HFlu) ligands and by two Cl atoms in a distorted octa-hedral geometry. Two Cl atoms bridge two Zn(II) atoms, forming a centrosymmetric dinuclear unit. The HFlu ligands connect the dinuclear units into a 4(4) net parallel to (001) when the dinuclear unit is considered as a node. O-H⋯O and O-H⋯Cl hydrogen bonds link the cationic layer, free chloride anions and lattice water mol-ecules. Intra-layer π-π inter-actions between the triazole rings are observed [centroid-centroid distance = 3.716 (6) Å].

Related literature

For background to this class of compounds, see: Han et al. (2006a ▶,b ▶). For related structures, see: Gao et al. (2001 ▶); Zhang et al. (2007 ▶).

Experimental

Crystal data

[ZnCl(C13H12F2N6O)2]Cl·2H2O

M = 784.89

Triclinic,

a = 10.2310 (6) Å

b = 11.8118 (6) Å

c = 14.3588 (9) Å

α = 91.191 (7)°

β = 107.481 (5)°

γ = 106.074 (6)°

V = 1580.11 (18) Å3

Z = 2

Mo Kα radiation

μ = 1.03 mm−1

T = 296 K

0.25 × 0.25 × 0.21 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2001 ▶) T min = 0.784, T max = 0.813

8374 measured reflections

5465 independent reflections

3137 reflections with I > 2σ(I)

R int = 0.064

Refinement

R[F 2 > 2σ(F 2)] = 0.080

wR(F 2) = 0.306

S = 1.07

5465 reflections

444 parameters

H-atom parameters constrained

Δρmax = 0.92 e Å−3

Δρmin = −1.09 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 1999 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536813026524/hy2637sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813026524/hy2637Isup2.hkl

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

[ZnCl(C13H12F2N6O)2]Cl·2H2O	Z = 2
Mr = 784.89	F(000) = 800
Triclinic, P1	Dx = 1.650 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.2310 (6) Å	Cell parameters from 859 reflections
b = 11.8118 (6) Å	θ = 2.2–22.1°
c = 14.3588 (9) Å	µ = 1.03 mm−1
α = 91.191 (7)°	T = 296 K
β = 107.481 (5)°	Block, colorless
γ = 106.074 (6)°	0.25 × 0.25 × 0.21 mm
V = 1580.11 (18) Å3

Bruker SMART 1000 CCD diffractometer	5465 independent reflections
Radiation source: fine-focus sealed tube	3137 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.064
φ and ω scans	θmax = 25.0°, θmin = 1.5°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −12→12
Tmin = 0.784, Tmax = 0.813	k = −14→12
8374 measured reflections	l = −14→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)] = 0.080	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.306	H-atom parameters constrained
S = 1.07	w = 1/[σ2(Fo2) + (0.1513P)2 + 4.0805P] where P = (Fo2 + 2Fc2)/3
5465 reflections	(Δ/σ)max < 0.001
444 parameters	Δρmax = 0.92 e Å−3
0 restraints	Δρmin = −1.09 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
Zn1	1.32995 (12)	0.41377 (10)	0.39336 (8)	0.0404 (4)
Cl1	1.4508 (3)	0.6199 (2)	0.45651 (17)	0.0448 (6)
Cl2	0.4395 (3)	0.9322 (2)	0.6822 (2)	0.0584 (8)
F1	0.7971 (10)	−0.0762 (7)	−0.0678 (5)	0.086 (2)
F2	0.6122 (9)	0.2436 (7)	−0.0664 (4)	0.083 (2)
F3	0.8098 (7)	0.2576 (6)	0.7540 (4)	0.0657 (18)
F4	1.2544 (8)	0.3386 (7)	0.9953 (4)	0.079 (2)
N1	0.5148 (8)	0.3554 (8)	0.1793 (5)	0.043 (2)
N2	0.5348 (9)	0.4724 (7)	0.1718 (6)	0.048 (2)
N3	0.4536 (8)	0.4152 (7)	0.2976 (5)	0.041 (2)
N4	1.1903 (9)	0.4025 (7)	0.4804 (5)	0.041 (2)
N5	1.0061 (8)	0.3403 (6)	0.5307 (5)	0.0335 (18)
N6	1.0891 (8)	0.4430 (6)	0.5911 (5)	0.0345 (18)
N7	1.1616 (8)	0.4340 (7)	0.2632 (5)	0.041 (2)
N8	1.0182 (9)	0.4016 (9)	0.1051 (6)	0.054 (2)
N9	0.9478 (8)	0.4220 (7)	0.1671 (5)	0.0388 (19)
N10	0.7509 (8)	−0.2201 (7)	0.6379 (5)	0.0393 (19)
N11	0.8367 (9)	−0.0419 (7)	0.7239 (6)	0.048 (2)
N12	0.7677 (8)	−0.0339 (7)	0.6293 (5)	0.0381 (19)
O1	0.7534 (7)	0.2765 (6)	0.2468 (4)	0.0446 (17)
H1	0.6956	0.2212	0.2602	0.067*
O2	0.9802 (7)	0.1089 (6)	0.5651 (4)	0.0417 (16)
H2	0.9323	0.0797	0.5087	0.063*
O3	0.5759 (12)	0.8041 (10)	0.3197 (8)	0.106 (4)
H3A	0.5660	0.8728	0.3247	0.127*
H3B	0.5394	0.7628	0.3585	0.127*
O4	0.1267 (8)	0.9438 (6)	0.6285 (5)	0.055 (2)
H4A	0.0960	0.9921	0.6543	0.065*
H4B	0.2165	0.9582	0.6394	0.065*
C1	0.7769 (15)	0.0150 (10)	−0.0176 (9)	0.061 (3)
C2	0.7008 (14)	0.0812 (11)	−0.0685 (8)	0.061 (3)
H2A	0.6611	0.0669	−0.1366	0.073*
C3	0.6831 (12)	0.1716 (11)	−0.0163 (8)	0.055 (3)
C4	0.7305 (10)	0.1914 (8)	0.0866 (6)	0.037 (2)
C5	0.8047 (12)	0.1152 (9)	0.1326 (7)	0.048 (3)
H5	0.8379	0.1228	0.2009	0.058*
C6	0.8309 (14)	0.0295 (9)	0.0817 (8)	0.059 (3)
H6	0.8848	−0.0178	0.1146	0.071*
C7	0.7064 (10)	0.2849 (8)	0.1446 (6)	0.038 (2)
C8	0.5481 (11)	0.2778 (9)	0.1112 (7)	0.044 (2)
H8A	0.5219	0.3018	0.0456	0.053*
H8B	0.4911	0.1963	0.1083	0.053*
C9	0.4661 (10)	0.3227 (9)	0.2527 (7)	0.043 (2)
H9	0.4441	0.2460	0.2701	0.051*
C10	0.4963 (11)	0.5041 (9)	0.2440 (7)	0.045 (2)
H10	0.4978	0.5816	0.2584	0.054*
C11	1.1463 (11)	0.4096 (10)	0.1657 (7)	0.050 (3)
H11	1.2202	0.3997	0.1446	0.060*
C12	1.0311 (11)	0.4394 (8)	0.2601 (7)	0.042 (2)
H12	1.0035	0.4532	0.3144	0.051*
C13	0.7955 (10)	0.4106 (9)	0.1330 (7)	0.045 (3)
H13A	0.7669	0.4244	0.0644	0.054*
H13B	0.7766	0.4699	0.1706	0.054*
C14	0.9018 (10)	0.1666 (8)	0.6051 (6)	0.035 (2)
C15	0.9956 (10)	0.2149 (8)	0.7112 (6)	0.036 (2)
C16	0.9466 (11)	0.2552 (8)	0.7784 (7)	0.043 (2)
C17	1.0282 (12)	0.2959 (9)	0.8753 (6)	0.047 (3)
H17	0.9900	0.3211	0.9202	0.056*
C18	1.1686 (12)	0.2967 (10)	0.9008 (6)	0.050 (3)
C19	1.2280 (12)	0.2644 (9)	0.8356 (7)	0.052 (3)
H19	1.3248	0.2691	0.8550	0.062*
C20	1.1427 (10)	0.2248 (8)	0.7411 (7)	0.040 (2)
H20	1.1826	0.2039	0.6955	0.048*
C21	0.7561 (10)	0.0805 (8)	0.5970 (7)	0.043 (2)
H21A	0.7120	0.1149	0.6367	0.052*
H21B	0.6944	0.0683	0.5292	0.052*
C22	0.7170 (11)	−0.1387 (9)	0.5789 (7)	0.045 (3)
H22	0.6653	−0.1546	0.5122	0.054*
C23	0.8252 (11)	−0.1510 (9)	0.7257 (7)	0.046 (3)
H23	0.8644	−0.1822	0.7827	0.056*
C24	1.0684 (10)	0.3188 (8)	0.4666 (6)	0.038 (2)
H24	1.0314	0.2539	0.4187	0.046*
C25	1.1980 (11)	0.4760 (8)	0.5568 (6)	0.038 (2)
H25	1.2742	0.5445	0.5829	0.045*
C26	0.8744 (10)	0.2674 (8)	0.5427 (7)	0.038 (2)
H26A	0.8054	0.2338	0.4787	0.046*
H26B	0.8341	0.3160	0.5745	0.046*

	U11	U22	U33	U12	U13	U23
Zn1	0.0408 (7)	0.0385 (7)	0.0419 (7)	0.0027 (5)	0.0216 (5)	−0.0007 (5)
Cl1	0.0473 (14)	0.0335 (13)	0.0487 (13)	0.0027 (11)	0.0168 (11)	0.0009 (10)
Cl2	0.0528 (16)	0.0554 (17)	0.0658 (17)	0.0127 (14)	0.0199 (13)	0.0137 (13)
F1	0.126 (7)	0.067 (5)	0.085 (5)	0.039 (5)	0.054 (5)	−0.006 (4)
F2	0.127 (7)	0.099 (6)	0.043 (4)	0.071 (5)	0.020 (4)	0.013 (3)
F3	0.048 (4)	0.095 (5)	0.059 (4)	0.027 (4)	0.019 (3)	−0.005 (3)
F4	0.073 (5)	0.105 (6)	0.040 (3)	0.023 (4)	−0.002 (3)	−0.014 (3)
N1	0.037 (4)	0.057 (6)	0.040 (4)	0.018 (4)	0.017 (3)	0.006 (4)
N2	0.052 (5)	0.038 (5)	0.060 (5)	0.008 (4)	0.030 (4)	0.008 (4)
N3	0.031 (4)	0.048 (5)	0.045 (4)	0.010 (4)	0.014 (3)	0.009 (4)
N4	0.044 (5)	0.045 (5)	0.037 (4)	0.012 (4)	0.019 (3)	0.009 (4)
N5	0.035 (4)	0.034 (4)	0.031 (4)	0.007 (3)	0.012 (3)	0.002 (3)
N6	0.035 (4)	0.037 (4)	0.036 (4)	0.009 (4)	0.019 (3)	0.003 (3)
N7	0.033 (4)	0.053 (5)	0.039 (4)	0.012 (4)	0.013 (3)	0.005 (4)
N8	0.039 (5)	0.091 (7)	0.038 (4)	0.022 (5)	0.021 (4)	0.004 (4)
N9	0.031 (4)	0.051 (5)	0.037 (4)	0.010 (4)	0.015 (3)	0.007 (4)
N10	0.042 (5)	0.039 (5)	0.042 (4)	0.009 (4)	0.023 (4)	0.011 (4)
N11	0.058 (5)	0.025 (4)	0.045 (4)	−0.005 (4)	0.008 (4)	−0.001 (3)
N12	0.043 (5)	0.036 (5)	0.033 (4)	0.005 (4)	0.014 (3)	0.009 (3)
O1	0.048 (4)	0.046 (4)	0.036 (3)	0.002 (3)	0.018 (3)	−0.002 (3)
O2	0.054 (4)	0.043 (4)	0.034 (3)	0.023 (3)	0.015 (3)	0.005 (3)
O3	0.112 (9)	0.096 (8)	0.138 (9)	0.039 (7)	0.071 (7)	0.047 (7)
O4	0.060 (5)	0.052 (5)	0.051 (4)	0.025 (4)	0.010 (3)	−0.002 (3)
C1	0.083 (9)	0.036 (6)	0.061 (7)	0.006 (6)	0.031 (6)	−0.010 (5)
C2	0.080 (9)	0.064 (8)	0.036 (6)	0.018 (7)	0.020 (5)	−0.011 (5)
C3	0.057 (7)	0.067 (8)	0.045 (6)	0.023 (6)	0.017 (5)	0.011 (5)
C4	0.038 (5)	0.040 (5)	0.035 (5)	0.011 (4)	0.015 (4)	0.007 (4)
C5	0.061 (7)	0.040 (6)	0.040 (5)	0.007 (5)	0.020 (5)	−0.005 (4)
C6	0.076 (8)	0.035 (6)	0.067 (7)	0.019 (6)	0.024 (6)	0.002 (5)
C7	0.035 (5)	0.039 (5)	0.038 (5)	0.009 (4)	0.013 (4)	0.002 (4)
C8	0.046 (6)	0.047 (6)	0.039 (5)	0.007 (5)	0.020 (4)	−0.009 (4)
C9	0.035 (5)	0.043 (6)	0.053 (6)	0.014 (5)	0.014 (4)	0.005 (5)
C10	0.050 (6)	0.031 (5)	0.053 (6)	0.007 (5)	0.020 (5)	−0.002 (4)
C11	0.037 (6)	0.083 (8)	0.036 (5)	0.020 (6)	0.020 (4)	0.010 (5)
C12	0.051 (6)	0.036 (5)	0.040 (5)	0.009 (5)	0.017 (4)	0.001 (4)
C13	0.041 (6)	0.049 (6)	0.056 (6)	0.023 (5)	0.020 (5)	0.015 (5)
C14	0.042 (5)	0.036 (5)	0.037 (5)	0.015 (4)	0.023 (4)	0.008 (4)
C15	0.048 (6)	0.031 (5)	0.034 (5)	0.010 (4)	0.021 (4)	0.011 (4)
C16	0.047 (6)	0.032 (5)	0.050 (6)	0.006 (5)	0.022 (5)	0.008 (4)
C17	0.057 (7)	0.057 (7)	0.030 (5)	0.019 (5)	0.018 (4)	0.001 (4)
C18	0.063 (7)	0.058 (7)	0.023 (5)	0.019 (6)	0.005 (5)	0.006 (4)
C19	0.044 (6)	0.049 (6)	0.051 (6)	0.003 (5)	0.009 (5)	−0.001 (5)
C20	0.035 (5)	0.044 (6)	0.044 (5)	0.011 (5)	0.018 (4)	0.004 (4)
C21	0.039 (5)	0.047 (6)	0.040 (5)	0.006 (5)	0.014 (4)	0.010 (4)
C22	0.048 (6)	0.046 (6)	0.034 (5)	0.001 (5)	0.016 (4)	−0.004 (4)
C23	0.053 (6)	0.038 (6)	0.040 (5)	0.001 (5)	0.014 (5)	0.001 (4)
C24	0.041 (5)	0.037 (5)	0.037 (5)	0.002 (4)	0.021 (4)	0.006 (4)
C25	0.046 (6)	0.025 (5)	0.039 (5)	0.005 (4)	0.015 (4)	−0.002 (4)
C26	0.045 (6)	0.035 (5)	0.042 (5)	0.016 (5)	0.020 (4)	0.010 (4)

Zn1—N3i	2.127 (8)	O4—H4B	0.8500
Zn1—N4	2.144 (8)	C1—C2	1.331 (16)
Zn1—N10ii	2.192 (8)	C1—C6	1.353 (15)
Zn1—N7	2.197 (7)	C2—C3	1.374 (15)
Zn1—Cl1	2.418 (3)	C2—H2A	0.9300
Zn1—Cl1iii	2.732 (3)	C3—C4	1.402 (13)
F1—C1	1.380 (13)	C4—C5	1.387 (13)
F2—C3	1.349 (12)	C4—C7	1.487 (13)
F3—C16	1.345 (12)	C5—C6	1.367 (15)
F4—C18	1.368 (11)	C5—H5	0.9300
N1—C9	1.317 (12)	C6—H6	0.9300
N1—N2	1.351 (11)	C7—C8	1.521 (13)
N1—C8	1.500 (12)	C7—C13	1.554 (13)
N2—C10	1.297 (13)	C8—H8A	0.9700
N3—C9	1.312 (13)	C8—H8B	0.9700
N3—C10	1.366 (12)	C9—H9	0.9300
N4—C24	1.317 (12)	C10—H10	0.9300
N4—C25	1.354 (12)	C11—H11	0.9300
N5—C24	1.323 (12)	C12—H12	0.9300
N5—N6	1.375 (10)	C13—H13A	0.9700
N5—C26	1.446 (12)	C13—H13B	0.9700
N6—C25	1.317 (12)	C14—C21	1.524 (13)
N7—C12	1.342 (13)	C14—C15	1.533 (12)
N7—C11	1.376 (12)	C14—C26	1.542 (11)
N8—C11	1.314 (12)	C15—C16	1.346 (14)
N8—N9	1.356 (11)	C15—C20	1.406 (13)
N9—C12	1.327 (11)	C16—C17	1.384 (13)
N9—C13	1.452 (12)	C17—C18	1.369 (15)
N10—C22	1.343 (12)	C17—H17	0.9300
N10—C23	1.367 (12)	C18—C19	1.359 (16)
N11—C23	1.262 (12)	C19—C20	1.363 (13)
N11—N12	1.350 (10)	C19—H19	0.9300
N12—C22	1.306 (12)	C20—H20	0.9300
N12—C21	1.462 (11)	C21—H21A	0.9700
O1—C7	1.415 (10)	C21—H21B	0.9700
O1—H1	0.8200	C22—H22	0.9300
O2—C14	1.415 (11)	C23—H23	0.9300
O2—H2	0.8200	C24—H24	0.9300
O3—H3A	0.8499	C25—H25	0.9300
O3—H3B	0.8500	C26—H26A	0.9700
O4—H4A	0.8500	C26—H26B	0.9700
N3i—Zn1—N4	175.2 (3)	N1—C8—C7	111.8 (8)
N3i—Zn1—N10ii	88.7 (3)	N1—C8—H8A	109.3
N4—Zn1—N10ii	88.0 (3)	C7—C8—H8A	109.3
N3i—Zn1—N7	86.0 (3)	N1—C8—H8B	109.3
N4—Zn1—N7	90.5 (3)	C7—C8—H8B	109.3
N10ii—Zn1—N7	91.2 (3)	H8A—C8—H8B	107.9
N3i—Zn1—Cl1	93.0 (2)	N3—C9—N1	109.5 (9)
N4—Zn1—Cl1	90.9 (2)	N3—C9—H9	125.3
N10ii—Zn1—Cl1	168.89 (19)	N1—C9—H9	125.3
N7—Zn1—Cl1	99.8 (2)	N2—C10—N3	115.1 (9)
N3i—Zn1—Cl1iii	89.1 (2)	N2—C10—H10	122.5
N4—Zn1—Cl1iii	94.2 (2)	N3—C10—H10	122.5
N10ii—Zn1—Cl1iii	86.6 (2)	N8—C11—N7	114.2 (10)
N7—Zn1—Cl1iii	174.7 (2)	N8—C11—H11	122.9
Cl1—Zn1—Cl1iii	82.44 (8)	N7—C11—H11	122.9
Zn1—Cl1—Zn1iii	97.56 (8)	N9—C12—N7	108.9 (9)
C9—N1—N2	111.4 (9)	N9—C12—H12	125.6
C9—N1—C8	126.6 (9)	N7—C12—H12	125.6
N2—N1—C8	122.0 (8)	N9—C13—C7	110.6 (7)
C10—N2—N1	101.5 (8)	N9—C13—H13A	109.5
C9—N3—C10	102.6 (8)	C7—C13—H13A	109.5
C9—N3—Zn1iv	127.0 (7)	N9—C13—H13B	109.5
C10—N3—Zn1iv	127.3 (7)	C7—C13—H13B	109.5
C24—N4—C25	103.4 (8)	H13A—C13—H13B	108.1
C24—N4—Zn1	125.4 (7)	O2—C14—C21	109.9 (8)
C25—N4—Zn1	131.1 (7)	O2—C14—C15	106.4 (7)
C24—N5—N6	110.1 (7)	C21—C14—C15	113.6 (7)
C24—N5—C26	127.4 (8)	O2—C14—C26	107.9 (7)
N6—N5—C26	122.4 (8)	C21—C14—C26	107.4 (7)
C25—N6—N5	101.7 (7)	C15—C14—C26	111.5 (8)
C12—N7—C11	102.9 (8)	C16—C15—C20	116.5 (9)
C12—N7—Zn1	126.3 (6)	C16—C15—C14	123.5 (9)
C11—N7—Zn1	128.3 (7)	C20—C15—C14	119.9 (9)
C11—N8—N9	102.4 (8)	C15—C16—F3	120.6 (9)
C12—N9—N8	111.5 (8)	C15—C16—C17	124.4 (10)
C12—N9—C13	126.0 (9)	F3—C16—C17	115.0 (10)
N8—N9—C13	122.1 (7)	C18—C17—C16	115.8 (10)
C22—N10—C23	101.2 (8)	C18—C17—H17	122.1
C22—N10—Zn1ii	128.2 (7)	C16—C17—H17	122.1
C23—N10—Zn1ii	129.6 (6)	C19—C18—C17	123.1 (9)
C23—N11—N12	103.6 (7)	C19—C18—F4	118.8 (10)
C22—N12—N11	110.1 (7)	C17—C18—F4	118.0 (10)
C22—N12—C21	129.4 (8)	C18—C19—C20	118.6 (10)
N11—N12—C21	120.5 (8)	C18—C19—H19	120.7
C7—O1—H1	109.5	C20—C19—H19	120.7
C14—O2—H2	109.5	C19—C20—C15	121.3 (10)
H3A—O3—H3B	108.7	C19—C20—H20	119.4
H4A—O4—H4B	119.4	C15—C20—H20	119.4
C2—C1—C6	123.2 (12)	N12—C21—C14	112.1 (8)
C2—C1—F1	118.7 (10)	N12—C21—H21A	109.2
C6—C1—F1	118.0 (11)	C14—C21—H21A	109.2
C1—C2—C3	117.2 (10)	N12—C21—H21B	109.2
C1—C2—H2A	121.4	C14—C21—H21B	109.2
C3—C2—H2A	121.4	H21A—C21—H21B	107.9
F2—C3—C2	118.5 (9)	N12—C22—N10	109.7 (8)
F2—C3—C4	117.7 (10)	N12—C22—H22	125.1
C2—C3—C4	123.8 (9)	N10—C22—H22	125.1
C5—C4—C3	114.2 (10)	N11—C23—N10	115.4 (8)
C5—C4—C7	121.1 (8)	N11—C23—H23	122.3
C3—C4—C7	124.7 (8)	N10—C23—H23	122.3
C6—C5—C4	122.7 (9)	N4—C24—N5	110.2 (9)
C6—C5—H5	118.6	N4—C24—H24	124.9
C4—C5—H5	118.6	N5—C24—H24	124.9
C1—C6—C5	118.6 (10)	N6—C25—N4	114.7 (8)
C1—C6—H6	120.7	N6—C25—H25	122.6
C5—C6—H6	120.7	N4—C25—H25	122.6
O1—C7—C4	112.2 (7)	N5—C26—C14	110.9 (7)
O1—C7—C8	109.6 (8)	N5—C26—H26A	109.5
C4—C7—C8	110.1 (8)	C14—C26—H26A	109.5
O1—C7—C13	104.5 (7)	N5—C26—H26B	109.5
C4—C7—C13	111.2 (8)	C14—C26—H26B	109.5
C8—C7—C13	109.0 (7)	H26A—C26—H26B	108.1

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···Cl2v	0.82	2.29	3.103 (7)	172
O2—H2···O4v	0.82	1.87	2.653 (9)	160
O3—H3A···Cl2vi	0.85	2.32	3.163 (11)	170
O3—H3B···Cl1iv	0.85	2.38	3.221 (10)	170
O4—H4A···O2vii	0.85	2.24	2.784 (9)	122
O4—H4B···Cl2	0.85	2.29	3.101 (8)	160

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯Cl2i	0.82	2.29	3.103 (7)	172
O2—H2⋯O4i	0.82	1.87	2.653 (9)	160
O3—H3A⋯Cl2ii	0.85	2.32	3.163 (11)	170
O3—H3B⋯Cl1iii	0.85	2.38	3.221 (10)	170
O4—H4A⋯O2iv	0.85	2.24	2.784 (9)	122
O4—H4B⋯Cl2	0.85	2.29	3.101 (8)	160

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