Bis(4-fluoro-benzoato-κO,O')bis-(nicotinamide-κN)zinc(II) monohydrate.

The title compound, [Zn(C(7)H(4)FO(2))(2)(C(6)H(6)N(2)O)(2)]·H(2)O, is a monomeric complex. It contains two 4-fluoro-benzoate and two nicotinamide ligands and one uncoordinated water mol-ecule. The 4-fluoro-benzoates act as bidentate chelating ligands, while the nicotinamides are monodentate. The six-coordinate geometry around the Zn(II) atom may be described as highly distorted octa-hedral, with the two nicotinamide ligands arranged cis. Inter-molecular O-H⋯O and N-H⋯O hydrogen bonds link the mol-ecules into a supra-molecular structure.

Related literature

For general background, see: Adiwidjaja et al. (1978 ▶); Amiraslanov et al. (1979 ▶); Antsyshkina et al. (1980 ▶); Bigoli et al. (1972 ▶); Day & Selbin (1969 ▶); Krishnamachari (1974 ▶); Nadzhafov, Shnulin & Mamedov (1981 ▶); Shnulin et al. (1981 ▶). For related structures, see: Amiraslanov et al. (1980 ▶); Capilla & Aranda (1979 ▶); Clegg et al. (1986a ▶,b ▶, 1987 ▶); Guseinov et al. (1984 ▶); Hökelek et al. (2007 ▶); Hökelek & Necefoğlu (1996 ▶, 2001 ▶); Nadzhafov, Usubaliev et al. (1981 ▶); Necefoğlu et al. (2002 ▶); Niekerk et al. (1953 ▶); Usubaliev et al. (1992 ▶).

Experimental

Crystal data

[Zn(C7H4FO2)2(C6H6N2O)2]·H2O

M = 605.87

Triclinic,

a = 8.2363 (2) Å

b = 12.3711 (2) Å

c = 14.8971 (3) Å

α = 113.178 (14)°

β = 99.015 (17)°

γ = 99.465 (16)°

V = 1334.7 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.99 mm−1

T = 294 (2) K

0.30 × 0.25 × 0.20 mm

Data collection

Enraf–Nonius TurboCAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.735, T max = 0.816

5794 measured reflections

5401 independent reflections

4454 reflections with I > 2σ(I)

R int = 0.058

3 standard reflections frequency: 120 min intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.058

wR(F 2) = 0.152

S = 1.14

5401 reflections

368 parameters

4 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.70 e Å−3

Δρmin = −0.90 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ▶); 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 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808003747/hy2118sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808003747/hy2118Isup2.hkl

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

[Zn(C7H4FO2)2(C6H6N2O)2]·H2O	Z = 2
Mr = 605.87	F000 = 620
Triclinic, P1	Dx = 1.508 Mg m−3
Hall symbol: -P 1	Mo Kα radiation λ = 0.71073 Å
a = 8.2363 (2) Å	Cell parameters from 25 reflections
b = 12.3711 (2) Å	θ = 6.3–15.8º
c = 14.8971 (3) Å	µ = 0.99 mm−1
α = 113.178 (14)º	T = 294 (2) K
β = 99.015 (17)º	Block, colorless
γ = 99.465 (16)º	0.30 × 0.25 × 0.20 mm
V = 1334.7 (2) Å3

Enraf–Nonius TurboCAD-4 diffractometer	Rint = 0.058
Radiation source: fine-focus sealed tube	θmax = 26.3º
Monochromator: graphite	θmin = 2.6º
T = 294(2) K	h = 0→10
ω scans	k = −15→15
Absorption correction: ψ scan(North et al., 1968)	l = −18→18
Tmin = 0.735, Tmax = 0.816	3 standard reflections
5794 measured reflections	every 120 min
5401 independent reflections	intensity decay: 1%
4454 reflections with I > 2σ(I)

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.058	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.152	w = 1/[σ2(Fo2) + (0.1013P)2 + 0.1012P] where P = (Fo2 + 2Fc2)/3
S = 1.14	(Δ/σ)max < 0.001
5401 reflections	Δρmax = 0.70 e Å−3
368 parameters	Δρmin = −0.90 e Å−3
4 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.052 (4)

	x	y	z	Uiso*/Ueq
Zn	0.39886 (4)	0.27400 (3)	0.12795 (2)	0.04482 (17)
F1	0.3683 (5)	−0.0772 (3)	−0.46673 (18)	0.1135 (10)
F2	1.3183 (4)	0.6557 (3)	0.5118 (2)	0.1174 (11)
O1	0.3504 (3)	0.14478 (19)	−0.01064 (16)	0.0548 (5)
O2	0.4950 (3)	0.30575 (19)	−0.01740 (17)	0.0551 (5)
O3	0.5801 (3)	0.4167 (3)	0.2340 (2)	0.0702 (7)
O4	0.6874 (4)	0.2602 (2)	0.1867 (2)	0.0769 (8)
O5	0.1224 (4)	0.1149 (2)	0.48350 (18)	0.0745 (8)
O6	−0.0625 (3)	0.71261 (19)	0.16243 (18)	0.0596 (6)
O7	0.2133 (11)	−0.0996 (5)	−0.0339 (6)	0.230 (4)
H71	0.295 (9)	−0.022 (4)	−0.005 (7)	0.237*
H72	0.260 (10)	−0.154 (6)	−0.078 (6)	0.237*
N1	0.3033 (3)	0.1816 (2)	0.20611 (18)	0.0459 (6)
N2	0.0163 (4)	−0.0739 (3)	0.3616 (2)	0.0637 (8)
H2A	−0.0266	−0.0998	0.4007	0.076*
H2B	0.0043	−0.1228	0.2996	0.076*
N3	0.2216 (3)	0.3771 (2)	0.12605 (18)	0.0447 (5)
N4	−0.2859 (4)	0.5519 (3)	0.0811 (2)	0.0590 (7)
H4A	−0.3543	0.5964	0.0773	0.071*
H4B	−0.3235	0.4743	0.0560	0.071*
C1	0.4207 (4)	0.1958 (3)	−0.0584 (2)	0.0456 (6)
C2	0.4091 (4)	0.1219 (3)	−0.1675 (2)	0.0468 (7)
C3	0.4631 (5)	0.1776 (3)	−0.2257 (3)	0.0686 (10)
H3	0.5087	0.2611	−0.1964	0.082*
C4	0.4501 (6)	0.1109 (4)	−0.3262 (3)	0.0845 (13)
H4	0.4858	0.1482	−0.3655	0.101*
C5	0.3844 (6)	−0.0099 (4)	−0.3665 (3)	0.0733 (10)
C6	0.3290 (6)	−0.0687 (3)	−0.3127 (3)	0.0720 (10)
H6	0.2827	−0.1522	−0.3432	0.086*
C7	0.3433 (5)	−0.0015 (3)	−0.2115 (3)	0.0616 (9)
H7	0.3081	−0.0400	−0.1729	0.074*
C8	0.7031 (4)	0.3684 (3)	0.2396 (2)	0.0561 (8)
C9	0.8671 (4)	0.4466 (3)	0.3131 (2)	0.0471 (7)
C10	0.8903 (5)	0.5711 (3)	0.3645 (3)	0.0576 (8)
H10	0.8025	0.6065	0.3537	0.069*
C11	1.0424 (5)	0.6425 (4)	0.4315 (3)	0.0723 (11)
H11	1.0592	0.7261	0.4657	0.087*
C12	1.1677 (5)	0.5872 (4)	0.4462 (3)	0.0720 (10)
C13	1.1497 (5)	0.4663 (4)	0.3980 (3)	0.0731 (11)
H13	1.2379	0.4319	0.4103	0.088*
C14	0.9975 (5)	0.3947 (3)	0.3299 (3)	0.0601 (8)
H14	0.9831	0.3114	0.2954	0.072*
C15	0.3619 (4)	0.2332 (3)	0.3051 (2)	0.0552 (8)
H15	0.4493	0.3037	0.3344	0.066*
C16	0.2988 (4)	0.1868 (3)	0.3668 (2)	0.0563 (8)
H16	0.3419	0.2268	0.4362	0.068*
C17	0.1730 (4)	0.0820 (3)	0.3253 (2)	0.0468 (7)
C18	0.1122 (5)	0.0265 (3)	0.2222 (3)	0.0710 (11)
H18	0.0274	−0.0455	0.1911	0.085*
C19	0.1796 (5)	0.0799 (4)	0.1658 (3)	0.0714 (11)
H19	0.1364	0.0430	0.0963	0.086*
C20	0.0998 (5)	0.0398 (3)	0.3964 (2)	0.0536 (8)
C21	0.0622 (4)	0.3283 (3)	0.0705 (2)	0.0474 (7)
H21	0.0288	0.2448	0.0311	0.057*
C22	−0.0549 (4)	0.3948 (3)	0.0684 (2)	0.0460 (6)
H22	−0.1649	0.3563	0.0288	0.055*
C23	−0.0092 (4)	0.5193 (2)	0.1254 (2)	0.0415 (6)
C24	0.1563 (4)	0.5696 (3)	0.1836 (2)	0.0535 (7)
H24	0.1932	0.6528	0.2237	0.064*
C25	0.2657 (4)	0.4967 (3)	0.1819 (3)	0.0539 (7)
H25	0.3760	0.5326	0.2217	0.065*
C26	−0.1227 (4)	0.6028 (3)	0.1256 (2)	0.0451 (6)

	U11	U22	U33	U12	U13	U23
Zn	0.0522 (2)	0.0428 (2)	0.0383 (2)	0.00425 (15)	0.01085 (15)	0.01931 (16)
F1	0.165 (3)	0.109 (2)	0.0478 (13)	0.020 (2)	0.0416 (16)	0.0141 (14)
F2	0.0804 (17)	0.103 (2)	0.097 (2)	−0.0022 (15)	−0.0312 (15)	0.0000 (17)
O1	0.0764 (15)	0.0430 (11)	0.0404 (11)	0.0061 (10)	0.0155 (10)	0.0162 (9)
O2	0.0579 (13)	0.0396 (11)	0.0532 (13)	0.0014 (9)	0.0015 (10)	0.0138 (10)
O3	0.0574 (14)	0.0737 (17)	0.0754 (17)	0.0012 (12)	−0.0024 (12)	0.0409 (14)
O4	0.0813 (18)	0.0568 (15)	0.0639 (16)	−0.0109 (13)	0.0102 (14)	0.0110 (13)
O5	0.118 (2)	0.0515 (13)	0.0494 (14)	−0.0009 (14)	0.0378 (14)	0.0188 (11)
O6	0.0685 (14)	0.0359 (11)	0.0611 (14)	0.0063 (10)	0.0086 (11)	0.0128 (10)
O7	0.314 (9)	0.100 (4)	0.263 (8)	0.007 (5)	0.209 (7)	0.032 (4)
N1	0.0529 (14)	0.0467 (13)	0.0400 (12)	0.0058 (11)	0.0124 (11)	0.0229 (11)
N2	0.094 (2)	0.0480 (15)	0.0496 (16)	0.0031 (15)	0.0304 (15)	0.0221 (13)
N3	0.0516 (13)	0.0441 (13)	0.0379 (12)	0.0068 (11)	0.0113 (10)	0.0190 (10)
N4	0.0539 (15)	0.0421 (13)	0.078 (2)	0.0074 (12)	0.0060 (14)	0.0285 (14)
C1	0.0475 (15)	0.0436 (15)	0.0431 (15)	0.0108 (12)	0.0083 (12)	0.0172 (12)
C2	0.0505 (16)	0.0437 (15)	0.0422 (15)	0.0080 (12)	0.0104 (12)	0.0164 (12)
C3	0.087 (3)	0.055 (2)	0.059 (2)	−0.0021 (18)	0.0273 (19)	0.0243 (17)
C4	0.110 (3)	0.086 (3)	0.063 (2)	0.008 (3)	0.039 (2)	0.037 (2)
C5	0.088 (3)	0.082 (3)	0.0430 (18)	0.020 (2)	0.0239 (18)	0.0166 (18)
C6	0.103 (3)	0.0466 (18)	0.0481 (19)	0.0094 (19)	0.0173 (19)	0.0058 (15)
C7	0.086 (2)	0.0482 (17)	0.0474 (18)	0.0106 (17)	0.0178 (17)	0.0196 (14)
C8	0.0600 (19)	0.065 (2)	0.0458 (17)	−0.0015 (16)	0.0115 (14)	0.0338 (16)
C9	0.0522 (16)	0.0520 (16)	0.0373 (14)	0.0053 (13)	0.0119 (12)	0.0219 (13)
C10	0.0627 (19)	0.0558 (18)	0.0514 (18)	0.0169 (15)	0.0130 (15)	0.0196 (15)
C11	0.082 (3)	0.051 (2)	0.056 (2)	0.0103 (18)	0.0054 (19)	0.0022 (16)
C12	0.059 (2)	0.074 (2)	0.051 (2)	0.0022 (18)	−0.0064 (16)	0.0081 (18)
C13	0.062 (2)	0.077 (3)	0.071 (2)	0.0246 (19)	0.0039 (19)	0.024 (2)
C14	0.069 (2)	0.0504 (18)	0.0531 (19)	0.0128 (16)	0.0121 (16)	0.0161 (15)
C15	0.0567 (18)	0.0554 (18)	0.0450 (16)	−0.0059 (15)	0.0072 (14)	0.0228 (14)
C16	0.0651 (19)	0.0599 (19)	0.0378 (15)	−0.0006 (15)	0.0093 (14)	0.0225 (14)
C17	0.0584 (17)	0.0448 (15)	0.0439 (15)	0.0130 (13)	0.0184 (13)	0.0235 (13)
C18	0.092 (3)	0.058 (2)	0.0443 (18)	−0.0178 (19)	0.0138 (18)	0.0188 (16)
C19	0.088 (3)	0.072 (2)	0.0381 (16)	−0.016 (2)	0.0103 (17)	0.0226 (16)
C20	0.072 (2)	0.0472 (16)	0.0471 (17)	0.0085 (15)	0.0245 (15)	0.0242 (14)
C21	0.0565 (17)	0.0362 (14)	0.0408 (14)	0.0014 (12)	0.0078 (13)	0.0133 (12)
C22	0.0476 (15)	0.0407 (14)	0.0402 (14)	−0.0001 (12)	0.0045 (12)	0.0145 (12)
C23	0.0504 (15)	0.0396 (14)	0.0349 (13)	0.0036 (12)	0.0121 (11)	0.0188 (11)
C24	0.0565 (18)	0.0373 (14)	0.0522 (17)	−0.0011 (13)	0.0031 (14)	0.0134 (13)
C25	0.0503 (17)	0.0437 (16)	0.0545 (18)	0.0015 (13)	0.0016 (14)	0.0159 (14)
C26	0.0553 (17)	0.0424 (15)	0.0373 (14)	0.0059 (13)	0.0117 (12)	0.0191 (12)

Zn—O1	1.978 (2)	C6—H6	0.9300
Zn—O2	2.564 (3)	C7—C6	1.379 (5)
Zn—O3	2.010 (3)	C7—H7	0.9300
Zn—O4	2.458 (3)	C9—C14	1.377 (5)
Zn—N1	2.079 (2)	C9—C10	1.386 (4)
Zn—N3	2.095 (3)	C9—C8	1.494 (4)
F1—C5	1.365 (4)	C10—H10	0.9300
F2—C12	1.354 (4)	C11—C10	1.376 (5)
O2—C1	1.246 (4)	C11—C12	1.364 (6)
O3—C8	1.264 (4)	C11—H11	0.9300
O4—C8	1.229 (4)	C12—C13	1.350 (6)
O5—C20	1.225 (4)	C13—H13	0.9300
O6—C26	1.224 (4)	C14—C13	1.384 (5)
O7—H71	0.97 (8)	C14—H14	0.9300
O7—H72	0.92 (8)	C15—C16	1.383 (4)
N1—C15	1.322 (4)	C15—H15	0.9300
N1—C19	1.332 (4)	C16—H16	0.9300
N2—C20	1.310 (4)	C17—C16	1.365 (4)
N2—H2A	0.8600	C17—C18	1.377 (4)
N2—H2B	0.8600	C17—C20	1.514 (4)
N3—C25	1.332 (4)	C18—H18	0.9300
N3—C21	1.333 (4)	C19—C18	1.382 (5)
N4—H4A	0.8600	C19—H19	0.9300
N4—H4B	0.8600	C21—H21	0.9300
C1—O1	1.266 (4)	C22—C21	1.372 (4)
C1—C2	1.497 (4)	C22—H22	0.9300
C2—C3	1.384 (4)	C23—C22	1.384 (4)
C2—C7	1.372 (4)	C23—C24	1.387 (4)
C3—C4	1.371 (6)	C23—C26	1.502 (4)
C3—H3	0.9300	C24—C25	1.371 (5)
C4—H4	0.9300	C24—H24	0.9300
C5—C4	1.346 (6)	C25—H25	0.9300
C5—C6	1.359 (6)	C26—N4	1.326 (4)
O1—Zn—O2	55.96 (12)	O4—C8—Zn	70.8 (2)
O1—Zn—O3	142.65 (12)	C9—C8—Zn	168.1 (3)
O1—Zn—O4	97.49 (10)	C10—C9—C8	120.9 (3)
O1—Zn—N1	102.97 (9)	C14—C9—C10	119.4 (3)
O1—Zn—N3	106.17 (10)	C14—C9—C8	119.7 (3)
O2—Zn—O3	93.35 (10)	C9—C10—H10	119.8
O2—Zn—O4	88.13 (10)	C11—C10—C9	120.4 (3)
O2—Zn—N1	158.51 (9)	C11—C10—H10	119.8
O2—Zn—N3	90.70 (9)	C10—C11—H11	120.9
O3—Zn—O4	57.04 (10)	C12—C11—C10	118.2 (3)
O3—Zn—N1	104.14 (10)	C12—C11—H11	120.9
O3—Zn—N3	93.66 (11)	F2—C12—C11	119.1 (4)
O4—Zn—N1	90.96 (10)	C13—C12—F2	117.7 (4)
O4—Zn—N3	150.53 (10)	C13—C12—C11	123.1 (3)
N1—Zn—N3	100.39 (10)	C12—C13—C14	118.7 (4)
C1—O1—Zn	104.58 (18)	C12—C13—H13	120.7
C8—O3—Zn	101.0 (2)	C14—C13—H13	120.7
C8—O4—Zn	81.0 (2)	C9—C14—C13	120.1 (3)
H72—O7—H71	107 (4)	C9—C14—H14	119.9
C15—N1—C19	117.5 (3)	C13—C14—H14	119.9
C15—N1—Zn	116.9 (2)	N1—C15—C16	122.8 (3)
C19—N1—Zn	125.4 (2)	N1—C15—H15	118.6
C20—N2—H2A	120.0	C16—C15—H15	118.6
C20—N2—H2B	120.0	C15—C16—H16	120.2
H2A—N2—H2B	120.0	C17—C16—C15	119.6 (3)
C21—N3—Zn	122.8 (2)	C17—C16—H16	120.2
C25—N3—C21	117.0 (3)	C16—C17—C18	118.1 (3)
C25—N3—Zn	120.2 (2)	C16—C17—C20	117.5 (3)
C26—N4—H4A	120.0	C18—C17—C20	124.2 (3)
C26—N4—H4B	120.0	C17—C18—C19	118.8 (3)
H4A—N4—H4B	120.0	C17—C18—H18	120.6
O1—C1—C2	118.5 (3)	C19—C18—H18	120.6
O2—C1—O1	121.6 (3)	N1—C19—C18	123.2 (3)
O2—C1—C2	119.8 (3)	N1—C19—H19	118.4
C3—C2—C1	120.2 (3)	C18—C19—H19	118.4
C7—C2—C3	119.1 (3)	O5—C20—N2	124.0 (3)
C7—C2—C1	120.7 (3)	O5—C20—C17	117.5 (3)
C2—C3—H3	119.7	N2—C20—C17	118.5 (3)
C4—C3—C2	120.7 (3)	N3—C21—C22	123.4 (3)
C4—C3—H3	119.7	N3—C21—H21	118.3
C3—C4—H4	120.8	C22—C21—H21	118.3
C5—C4—C3	118.4 (4)	C21—C22—C23	119.9 (3)
C5—C4—H4	120.8	C21—C22—H22	120.0
C4—C5—C6	123.2 (3)	C23—C22—H22	120.0
C4—C5—F1	119.1 (4)	C22—C23—C24	116.5 (3)
C6—C5—F1	117.8 (4)	C22—C23—C26	125.0 (3)
C5—C6—C7	118.3 (3)	C24—C23—C26	118.5 (3)
C5—C6—H6	120.9	C23—C24—H24	120.0
C7—C6—H6	120.9	C25—C24—C23	120.1 (3)
C2—C7—C6	120.4 (3)	C25—C24—H24	120.0
C2—C7—H7	119.8	N3—C25—C24	123.2 (3)
C6—C7—H7	119.8	N3—C25—H25	118.4
O3—C8—Zn	50.10 (17)	C24—C25—H25	118.4
O3—C8—C9	118.0 (3)	O6—C26—N4	122.7 (3)
O4—C8—O3	120.9 (3)	O6—C26—C23	120.1 (3)
O4—C8—C9	121.1 (3)	N4—C26—C23	117.2 (3)
O1—Zn—N1—C15	159.4 (2)	C3—C2—C7—C6	−0.9 (6)
O1—Zn—N1—C19	−25.8 (3)	C1—C2—C7—C6	178.4 (4)
O3—Zn—N1—C15	5.4 (3)	C7—C2—C3—C4	0.5 (6)
O3—Zn—N1—C19	−179.9 (3)	C1—C2—C3—C4	−178.8 (4)
O4—Zn—N1—C15	61.5 (3)	C6—C5—C4—C3	0.6 (8)
O4—Zn—N1—C19	−123.7 (3)	F1—C5—C4—C3	179.0 (4)
N3—Zn—N1—C15	−91.1 (3)	C2—C3—C4—C5	−0.3 (7)
N3—Zn—N1—C19	83.6 (3)	C4—C5—C6—C7	−1.0 (7)
O1—Zn—N3—C21	35.9 (2)	F1—C5—C6—C7	−179.4 (4)
O1—Zn—N3—C25	−144.1 (2)	C2—C7—C6—C5	1.1 (6)
O3—Zn—N3—C21	−176.1 (2)	C14—C9—C8—O4	−6.9 (4)
O3—Zn—N3—C25	3.9 (2)	C10—C9—C8—O4	172.9 (3)
O4—Zn—N3—C21	178.0 (2)	C14—C9—C8—O3	172.5 (3)
O4—Zn—N3—C25	−2.0 (3)	C10—C9—C8—O3	−7.7 (4)
N1—Zn—N3—C21	−71.0 (2)	C14—C9—C8—Zn	170.6 (8)
N1—Zn—N3—C25	109.0 (2)	C10—C9—C8—Zn	−9.6 (12)
O3—Zn—O1—C1	−38.7 (3)	C14—C9—C10—C11	0.3 (5)
O4—Zn—O1—C1	−81.6 (2)	C8—C9—C10—C11	−179.5 (3)
N1—Zn—O1—C1	−174.32 (19)	C10—C9—C14—C13	0.4 (5)
N3—Zn—O1—C1	80.6 (2)	C8—C9—C14—C13	−179.8 (3)
O1—Zn—O3—C8	−53.5 (3)	C12—C11—C10—C9	−0.7 (6)
N1—Zn—O3—C8	81.8 (2)	C10—C11—C12—C13	0.4 (7)
N3—Zn—O3—C8	−176.5 (2)	C10—C11—C12—F2	180.0 (4)
O4—Zn—O3—C8	0.04 (18)	F2—C12—C13—C14	−179.3 (4)
O1—Zn—O4—C8	150.46 (19)	C11—C12—C13—C14	0.3 (7)
O3—Zn—O4—C8	−0.04 (19)	C9—C14—C13—C12	−0.7 (6)
N1—Zn—O4—C8	−106.3 (2)	N1—C15—C16—C17	1.3 (6)
N3—Zn—O4—C8	7.0 (3)	C18—C17—C16—C15	−0.5 (5)
Zn—O3—C8—O4	−0.1 (4)	C20—C17—C16—C15	−175.8 (3)
Zn—O3—C8—C9	−179.5 (2)	C16—C17—C18—C19	−0.7 (6)
Zn—O4—C8—O3	0.1 (3)	C20—C17—C18—C19	174.2 (4)
Zn—O4—C8—C9	179.5 (3)	C16—C17—C20—O5	19.1 (5)
C19—N1—C15—C16	−0.8 (6)	C18—C17—C20—O5	−155.9 (4)
Zn—N1—C15—C16	174.4 (3)	C16—C17—C20—N2	−161.1 (3)
C15—N1—C19—C18	−0.5 (6)	C18—C17—C20—N2	23.9 (5)
Zn—N1—C19—C18	−175.2 (3)	N1—C19—C18—C17	1.3 (7)
C25—N3—C21—C22	0.2 (4)	C23—C22—C21—N3	0.6 (5)
Zn—N3—C21—C22	−179.8 (2)	C24—C23—C22—C21	−0.9 (4)
C21—N3—C25—C24	−0.5 (5)	C26—C23—C22—C21	176.7 (3)
Zn—N3—C25—C24	179.5 (3)	C22—C23—C24—C25	0.6 (5)
O2—C1—O1—Zn	−2.1 (3)	C26—C23—C24—C25	−177.2 (3)
C2—C1—O1—Zn	179.6 (2)	C23—C24—C25—N3	0.1 (5)
O2—C1—C2—C7	173.3 (3)	C22—C23—C26—O6	−165.7 (3)
O1—C1—C2—C7	−8.3 (5)	C24—C23—C26—O6	11.9 (4)
O2—C1—C2—C3	−7.4 (5)	C22—C23—C26—N4	11.7 (4)
O1—C1—C2—C3	171.0 (3)	C24—C23—C26—N4	−170.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
O7—H71···O1	0.97 (7)	2.08 (7)	2.910 (8)	144 (6)
O7—H72···O4i	0.92 (8)	1.81 (8)	2.713 (10)	167 (8)
N2—H2A···O5ii	0.86	2.07	2.905 (4)	165
N2—H2B···O6iii	0.86	2.15	2.977 (4)	161
N4—H4A···O2iv	0.86	2.14	2.961 (4)	159
N4—H4B···O2v	0.86	2.11	2.920 (4)	157

Zn—O1	1.978 (2)
Zn—O2	2.564 (3)
Zn—O3	2.010 (3)
Zn—O4	2.458 (3)
Zn—N1	2.079 (2)
Zn—N3	2.095 (3)

O1—Zn—O2	55.96 (12)
O1—Zn—O3	142.65 (12)
O1—Zn—O4	97.49 (10)
O1—Zn—N1	102.97 (9)
O1—Zn—N3	106.17 (10)
O2—Zn—O3	93.35 (10)
O2—Zn—O4	88.13 (10)
O2—Zn—N1	158.51 (9)
O2—Zn—N3	90.70 (9)
O3—Zn—O4	57.04 (10)
O3—Zn—N1	104.14 (10)
O3—Zn—N3	93.66 (11)
O4—Zn—N1	90.96 (10)
O4—Zn—N3	150.53 (10)
N1—Zn—N3	100.39 (10)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7—H71⋯O1	0.97 (7)	2.08 (7)	2.910 (8)	144 (6)
O7—H72⋯O4i	0.92 (8)	1.81 (8)	2.713 (10)	167 (8)
N2—H2A⋯O5ii	0.86	2.07	2.905 (4)	165
N2—H2B⋯O6iii	0.86	2.15	2.977 (4)	161
N4—H4A⋯O2iv	0.86	2.14	2.961 (4)	159
N4—H4B⋯O2v	0.86	2.11	2.920 (4)	157

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