Aqua-(3-fluoro-benzoato-κO)(3-fluoro-benzoato-κO,O')(1,10-phenanthroline-κN,N')cobalt(II).

In the title compound, [Co(C(7)H(4)FO(2))(2)(C(12)H(8)N(2))(H(2)O)], the Co(II) ion is coordinated by two O atoms from one 3-fluoro-benzoate (fb) ligand and one O atom from another fb ligand, two N atoms from the 1,10-phenanthroline ligand and a water mol-ecule in a distorted octa-hedral geometry. An intra-molecular O-H⋯O hydrogen bond occurs. Inter-molecular O-H⋯O hydrogen bonds link pairs of mol-ecules into centrosymmetric dimers. Weak inter-molecular C-H⋯O and C-H⋯F hydrogen bonds and π-π inter-actions between the aromatic rings [shortest centroid-centroid distance = 3.4962 (2) Å] further stabilize the crystal packing.

Related literature

For the crystal structures of related metal complexes with 3-fluoro­benzoic acid, see: Sevryugina et al. (2007 ▶); Motokawa et al. (2008 ▶); Wein et al. (2009 ▶); Yin (2011 ▶); Miyasaka et al. (2011 ▶).

Experimental

Crystal data

[Co(C7H4FO2)2(C12H8N2)(H2O)]

M = 535.35

Triclinic,

a = 8.6517 (7) Å

b = 12.1233 (10) Å

c = 12.6752 (10) Å

α = 64.045 (1)°

β = 88.879 (1)°

γ = 72.892 (1)°

V = 1133.22 (16) Å3

Z = 2

Mo Kα radiation

μ = 0.82 mm−1

T = 298 K

0.30 × 0.20 × 0.12 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.792, T max = 0.908

4724 measured reflections

3980 independent reflections

3119 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.105

S = 1.03

3980 reflections

333 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.73 e Å−3

Δρmin = −0.39 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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.

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811051804/cv5209sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811051804/cv5209Isup2.hkl

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

[Co(C7H4FO2)2(C12H8N2)(H2O)]	Z = 2
Mr = 535.35	F(000) = 546
Triclinic, P1	Dx = 1.569 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6517 (7) Å	Cell parameters from 2450 reflections
b = 12.1233 (10) Å	θ = 2.6–26.0°
c = 12.6752 (10) Å	µ = 0.82 mm−1
α = 64.045 (1)°	T = 298 K
β = 88.879 (1)°	Block, purple
γ = 72.892 (1)°	0.30 × 0.20 × 0.12 mm
V = 1133.22 (16) Å3

Bruker SMART APEXII CCD area-detector diffractometer	3980 independent reflections
Radiation source: fine-focus sealed tube	3119 reflections with I > 2σ(I)
graphite	Rint = 0.032
φ and ω scans	θmax = 25.0°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→10
Tmin = 0.792, Tmax = 0.908	k = −14→10
4724 measured reflections	l = −14→15

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ2(Fo2) + (0.055P)2 + 0.0202P] where P = (Fo2 + 2Fc2)/3
3980 reflections	(Δ/σ)max < 0.001
333 parameters	Δρmax = 0.73 e Å−3
0 restraints	Δρmin = −0.39 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
Co1	0.51799 (4)	0.24471 (3)	0.12214 (3)	0.03633 (15)
F2	1.0969 (3)	−0.26008 (18)	0.56566 (17)	0.0808 (7)
F1	0.1529 (3)	0.3143 (2)	0.60217 (19)	0.0947 (8)
O5	0.6418 (3)	0.32022 (19)	−0.02002 (18)	0.0433 (5)
O3	0.7374 (2)	0.12837 (18)	0.22283 (17)	0.0447 (5)
O1	0.4668 (2)	0.41857 (18)	0.16171 (17)	0.0471 (5)
O2	0.4068 (2)	0.24361 (19)	0.27285 (18)	0.0495 (5)
O4	0.9083 (2)	0.2289 (2)	0.12131 (18)	0.0584 (6)
N2	0.4584 (3)	0.0844 (2)	0.13322 (19)	0.0356 (5)
N1	0.3025 (3)	0.3333 (2)	−0.0037 (2)	0.0407 (6)
C8	0.8765 (3)	0.1430 (3)	0.2093 (2)	0.0376 (6)
C25	0.3329 (3)	0.1120 (3)	0.0540 (2)	0.0343 (6)
C1	0.4124 (3)	0.3528 (3)	0.2530 (2)	0.0380 (7)
C2	0.3542 (3)	0.4031 (3)	0.3406 (2)	0.0381 (7)
C9	1.0117 (3)	0.0474 (3)	0.3071 (2)	0.0364 (6)
C4	0.2237 (4)	0.3823 (3)	0.5107 (3)	0.0573 (8)
C21	0.2827 (3)	0.0175 (3)	0.0433 (3)	0.0414 (7)
C26	0.2505 (3)	0.2470 (3)	−0.0217 (2)	0.0354 (6)
C24	0.5326 (4)	−0.0398 (3)	0.2070 (3)	0.0442 (7)
H24	0.6190	−0.0609	0.2621	0.053*
C10	0.9929 (4)	−0.0668 (3)	0.3921 (3)	0.0443 (7)
H10	0.8981	−0.0870	0.3881	0.053*
C18	0.1238 (3)	0.2816 (3)	−0.1082 (3)	0.0435 (7)
C3	0.2792 (3)	0.3340 (3)	0.4326 (3)	0.0455 (7)
H3	0.2668	0.2570	0.4411	0.055*
C15	0.2255 (4)	0.4583 (3)	−0.0715 (3)	0.0526 (8)
H15	0.2583	0.5190	−0.0598	0.063*
C20	0.1565 (4)	0.0568 (3)	−0.0480 (3)	0.0523 (8)
H20	0.1251	−0.0058	−0.0575	0.063*
C22	0.3644 (4)	−0.1114 (3)	0.1232 (3)	0.0519 (8)
H22	0.3348	−0.1778	0.1201	0.062*
C14	1.1547 (3)	0.0739 (3)	0.3155 (3)	0.0468 (7)
H14	1.1689	0.1496	0.2581	0.056*
C11	1.1172 (4)	−0.1490 (3)	0.4818 (3)	0.0524 (8)
C7	0.3732 (4)	0.5164 (3)	0.3303 (3)	0.0509 (8)
H7	0.4254	0.5616	0.2692	0.061*
C13	1.2761 (4)	−0.0106 (3)	0.4081 (3)	0.0590 (9)
H13	1.3712	0.0086	0.4134	0.071*
C17	0.0479 (4)	0.4149 (3)	−0.1789 (3)	0.0569 (9)
H17	−0.0359	0.4434	−0.2387	0.068*
C23	0.4859 (4)	−0.1390 (3)	0.2047 (3)	0.0520 (8)
H23	0.5383	−0.2244	0.2593	0.062*
C19	0.0811 (4)	0.1834 (3)	−0.1213 (3)	0.0536 (9)
H19	0.0000	0.2064	−0.1812	0.064*
C5	0.2395 (4)	0.4944 (3)	0.5024 (3)	0.0651 (10)
H5A	0.2002	0.5240	0.5573	0.078*
C6	0.3151 (5)	0.5636 (4)	0.4105 (3)	0.0647 (9)
H6	0.3268	0.6405	0.4027	0.078*
C16	0.0966 (4)	0.5018 (3)	−0.1600 (3)	0.0644 (10)
H16	0.0449	0.5900	−0.2056	0.077*
C12	1.2573 (4)	−0.1229 (3)	0.4924 (3)	0.0601 (9)
H12	1.3384	−0.1802	0.5555	0.072*
H1	0.7360 (17)	0.299 (3)	0.016 (2)	0.071 (12)*
H2	0.613 (3)	0.4010 (6)	−0.066 (2)	0.067 (11)*

	U11	U22	U33	U12	U13	U23
Co1	0.0391 (2)	0.0317 (2)	0.0372 (2)	−0.01239 (17)	0.00096 (17)	−0.01383 (18)
F2	0.1046 (17)	0.0410 (11)	0.0648 (13)	−0.0093 (11)	−0.0002 (12)	−0.0042 (10)
F1	0.1097 (19)	0.1022 (18)	0.0730 (14)	−0.0412 (15)	0.0432 (13)	−0.0369 (13)
O5	0.0520 (14)	0.0336 (12)	0.0385 (12)	−0.0135 (10)	0.0016 (10)	−0.0112 (10)
O3	0.0381 (11)	0.0401 (11)	0.0451 (12)	−0.0147 (9)	−0.0004 (9)	−0.0082 (9)
O1	0.0589 (13)	0.0363 (10)	0.0421 (12)	−0.0120 (10)	0.0096 (10)	−0.0162 (9)
O2	0.0576 (13)	0.0451 (12)	0.0556 (13)	−0.0235 (11)	0.0142 (10)	−0.0269 (11)
O4	0.0484 (13)	0.0549 (14)	0.0503 (13)	−0.0234 (11)	0.0023 (10)	−0.0004 (11)
N2	0.0351 (13)	0.0318 (12)	0.0375 (13)	−0.0105 (10)	0.0061 (10)	−0.0138 (11)
N1	0.0438 (14)	0.0316 (13)	0.0421 (14)	−0.0111 (11)	0.0003 (11)	−0.0131 (11)
C8	0.0397 (17)	0.0350 (15)	0.0408 (16)	−0.0129 (13)	0.0036 (13)	−0.0188 (14)
C25	0.0331 (15)	0.0353 (15)	0.0389 (15)	−0.0129 (12)	0.0101 (12)	−0.0196 (13)
C1	0.0315 (15)	0.0375 (16)	0.0377 (16)	−0.0058 (13)	−0.0031 (13)	−0.0137 (13)
C2	0.0343 (15)	0.0349 (15)	0.0370 (16)	−0.0031 (13)	−0.0038 (12)	−0.0137 (13)
C9	0.0354 (15)	0.0351 (15)	0.0377 (16)	−0.0078 (13)	0.0048 (12)	−0.0177 (13)
C4	0.056 (2)	0.059 (2)	0.0445 (18)	−0.0064 (16)	0.0076 (14)	−0.0200 (16)
C21	0.0423 (17)	0.0457 (17)	0.0499 (18)	−0.0216 (14)	0.0171 (14)	−0.0290 (15)
C26	0.0329 (15)	0.0396 (15)	0.0377 (15)	−0.0136 (13)	0.0068 (12)	−0.0197 (13)
C24	0.0495 (18)	0.0344 (16)	0.0424 (17)	−0.0117 (14)	0.0068 (14)	−0.0130 (14)
C10	0.0444 (17)	0.0380 (17)	0.0479 (18)	−0.0106 (14)	0.0030 (14)	−0.0186 (14)
C18	0.0347 (16)	0.0515 (19)	0.0453 (17)	−0.0140 (14)	0.0047 (13)	−0.0225 (15)
C3	0.0464 (18)	0.0393 (16)	0.0444 (17)	−0.0081 (14)	0.0039 (14)	−0.0168 (14)
C15	0.056 (2)	0.0353 (17)	0.058 (2)	−0.0092 (15)	−0.0075 (16)	−0.0157 (15)
C20	0.0493 (19)	0.067 (2)	0.067 (2)	−0.0310 (18)	0.0162 (17)	−0.0461 (19)
C22	0.062 (2)	0.0423 (19)	0.068 (2)	−0.0268 (17)	0.0216 (18)	−0.0329 (17)
C14	0.0410 (17)	0.0512 (19)	0.0459 (18)	−0.0136 (15)	0.0075 (14)	−0.0205 (15)
C11	0.065 (2)	0.0330 (17)	0.0421 (18)	−0.0021 (16)	0.0036 (16)	−0.0106 (15)
C7	0.060 (2)	0.0481 (18)	0.0477 (18)	−0.0203 (17)	0.0085 (16)	−0.0227 (16)
C13	0.0378 (18)	0.075 (3)	0.056 (2)	−0.0111 (17)	0.0021 (16)	−0.027 (2)
C17	0.0423 (18)	0.062 (2)	0.058 (2)	−0.0108 (17)	−0.0092 (16)	−0.0229 (18)
C23	0.062 (2)	0.0299 (16)	0.057 (2)	−0.0140 (15)	0.0136 (17)	−0.0144 (15)
C19	0.0384 (18)	0.080 (3)	0.057 (2)	−0.0253 (18)	0.0046 (15)	−0.040 (2)
C5	0.072 (2)	0.067 (2)	0.060 (2)	−0.009 (2)	0.0108 (19)	−0.040 (2)
C6	0.079 (2)	0.059 (2)	0.065 (2)	−0.021 (2)	0.011 (2)	−0.0368 (19)
C16	0.060 (2)	0.047 (2)	0.061 (2)	−0.0019 (18)	−0.0139 (18)	−0.0116 (18)
C12	0.048 (2)	0.062 (2)	0.050 (2)	0.0102 (18)	−0.0089 (16)	−0.0242 (18)

Co1—O3	2.0412 (19)	C26—C18	1.397 (4)
Co1—O5	2.071 (2)	C24—C23	1.388 (4)
Co1—N2	2.101 (2)	C24—H24	0.9300
Co1—O2	2.118 (2)	C10—C11	1.367 (4)
Co1—N1	2.147 (2)	C10—H10	0.9300
Co1—O1	2.2930 (19)	C18—C17	1.406 (4)
F2—C11	1.361 (4)	C18—C19	1.420 (4)
F1—C4	1.354 (4)	C3—H3	0.9300
O5—H1	0.8500 (11)	C15—C16	1.403 (4)
O5—H2	0.8499 (11)	C15—H15	0.9300
O3—C8	1.265 (3)	C20—C19	1.353 (4)
O1—C1	1.261 (3)	C20—H20	0.9300
O2—C1	1.250 (3)	C22—C23	1.348 (4)
O4—C8	1.243 (3)	C22—H22	0.9300
N2—C24	1.333 (3)	C14—C13	1.375 (4)
N2—C25	1.354 (3)	C14—H14	0.9300
N1—C15	1.330 (3)	C11—C12	1.362 (5)
N1—C26	1.356 (3)	C7—C6	1.390 (4)
C8—C9	1.500 (4)	C7—H7	0.9300
C25—C21	1.397 (4)	C13—C12	1.367 (5)
C25—C26	1.440 (4)	C13—H13	0.9300
C1—C2	1.498 (4)	C17—C16	1.352 (5)
C2—C7	1.382 (4)	C17—H17	0.9300
C2—C3	1.385 (4)	C23—H23	0.9300
C9—C14	1.384 (4)	C19—H19	0.9300
C9—C10	1.387 (4)	C5—C6	1.387 (5)
C4—C5	1.364 (5)	C5—H5A	0.9300
C4—C3	1.370 (4)	C6—H6	0.9300
C21—C22	1.400 (4)	C16—H16	0.9300
C21—C20	1.421 (4)	C12—H12	0.9300
O3—Co1—O5	88.75 (8)	C23—C24—H24	118.7
O3—Co1—N2	91.47 (8)	C11—C10—C9	118.3 (3)
O5—Co1—N2	113.37 (8)	C11—C10—H10	120.9
O3—Co1—O2	91.55 (8)	C9—C10—H10	120.9
O5—Co1—O2	152.67 (8)	C26—C18—C17	116.3 (3)
N2—Co1—O2	93.94 (8)	C26—C18—C19	119.6 (3)
O3—Co1—N1	165.19 (8)	C17—C18—C19	124.1 (3)
O5—Co1—N1	86.87 (9)	C4—C3—C2	118.1 (3)
N2—Co1—N1	77.36 (8)	C4—C3—H3	121.0
O2—Co1—N1	98.81 (8)	C2—C3—H3	121.0
O3—Co1—O1	101.55 (8)	N1—C15—C16	122.3 (3)
O5—Co1—O1	94.09 (8)	N1—C15—H15	118.9
N2—Co1—O1	149.92 (8)	C16—C15—H15	118.9
O2—Co1—O1	59.10 (7)	C19—C20—C21	121.3 (3)
N1—Co1—O1	92.87 (8)	C19—C20—H20	119.4
Co1—O5—H1	101 (2)	C21—C20—H20	119.4
Co1—O5—H2	121 (2)	C23—C22—C21	119.9 (3)
H1—O5—H2	107.6 (19)	C23—C22—H22	120.1
C8—O3—Co1	129.55 (18)	C21—C22—H22	120.1
C1—O1—Co1	86.01 (16)	C13—C14—C9	120.6 (3)
C1—O2—Co1	94.26 (17)	C13—C14—H14	119.7
C24—N2—C25	117.4 (2)	C9—C14—H14	119.7
C24—N2—Co1	127.2 (2)	F2—C11—C12	119.1 (3)
C25—N2—Co1	115.39 (17)	F2—C11—C10	117.9 (3)
C15—N1—C26	117.5 (2)	C12—C11—C10	123.0 (3)
C15—N1—Co1	128.8 (2)	C2—C7—C6	120.6 (3)
C26—N1—Co1	113.42 (17)	C2—C7—H7	119.7
O4—C8—O3	124.8 (3)	C6—C7—H7	119.7
O4—C8—C9	118.6 (2)	C12—C13—C14	120.2 (3)
O3—C8—C9	116.6 (2)	C12—C13—H13	119.9
N2—C25—C21	123.4 (3)	C14—C13—H13	119.9
N2—C25—C26	116.4 (2)	C16—C17—C18	120.1 (3)
C21—C25—C26	120.1 (2)	C16—C17—H17	119.9
O2—C1—O1	120.6 (3)	C18—C17—H17	119.9
O2—C1—C2	118.6 (3)	C22—C23—C24	119.9 (3)
O1—C1—C2	120.9 (3)	C22—C23—H23	120.1
C7—C2—C3	120.0 (3)	C24—C23—H23	120.1
C7—C2—C1	121.2 (3)	C20—C19—C18	120.9 (3)
C3—C2—C1	118.7 (3)	C20—C19—H19	119.5
C14—C9—C10	119.3 (3)	C18—C19—H19	119.5
C14—C9—C8	120.3 (2)	C4—C5—C6	118.7 (3)
C10—C9—C8	120.4 (2)	C4—C5—H5A	120.6
F1—C4—C5	118.2 (3)	C6—C5—H5A	120.6
F1—C4—C3	118.5 (3)	C5—C6—C7	119.2 (3)
C5—C4—C3	123.3 (3)	C5—C6—H6	120.4
C25—C21—C22	116.8 (3)	C7—C6—H6	120.4
C25—C21—C20	118.9 (3)	C17—C16—C15	119.7 (3)
C22—C21—C20	124.3 (3)	C17—C16—H16	120.2
N1—C26—C18	124.1 (3)	C15—C16—H16	120.2
N1—C26—C25	116.8 (2)	C11—C12—C13	118.6 (3)
C18—C26—C25	119.1 (3)	C11—C12—H12	120.7
N2—C24—C23	122.6 (3)	C13—C12—H12	120.7
N2—C24—H24	118.7
O5—Co1—O3—C8	23.8 (2)	N2—C25—C21—C22	2.8 (4)
N2—Co1—O3—C8	137.1 (2)	C26—C25—C21—C22	−177.4 (3)
O2—Co1—O3—C8	−128.9 (2)	N2—C25—C21—C20	−175.9 (3)
N1—Co1—O3—C8	96.5 (4)	C26—C25—C21—C20	3.9 (4)
O1—Co1—O3—C8	−70.2 (2)	C15—N1—C26—C18	1.3 (4)
O3—Co1—O1—C1	−83.30 (16)	Co1—N1—C26—C18	−172.9 (2)
O5—Co1—O1—C1	−172.86 (16)	C15—N1—C26—C25	−178.8 (3)
N2—Co1—O1—C1	30.6 (2)	Co1—N1—C26—C25	7.0 (3)
O2—Co1—O1—C1	1.53 (15)	N2—C25—C26—N1	−2.2 (4)
N1—Co1—O1—C1	100.08 (16)	C21—C25—C26—N1	177.9 (2)
O3—Co1—O2—C1	101.01 (17)	N2—C25—C26—C18	177.7 (2)
O5—Co1—O2—C1	10.7 (3)	C21—C25—C26—C18	−2.1 (4)
N2—Co1—O2—C1	−167.41 (16)	C25—N2—C24—C23	0.0 (4)
N1—Co1—O2—C1	−89.61 (17)	Co1—N2—C24—C23	−178.2 (2)
O1—Co1—O2—C1	−1.54 (15)	C14—C9—C10—C11	0.4 (4)
O3—Co1—N2—C24	13.8 (2)	C8—C9—C10—C11	−177.7 (2)
O5—Co1—N2—C24	103.0 (2)	N1—C26—C18—C17	−0.3 (4)
O2—Co1—N2—C24	−77.9 (2)	C25—C26—C18—C17	179.7 (3)
N1—Co1—N2—C24	−176.0 (2)	N1—C26—C18—C19	178.7 (3)
O1—Co1—N2—C24	−102.6 (3)	C25—C26—C18—C19	−1.2 (4)
O3—Co1—N2—C25	−164.44 (18)	F1—C4—C3—C2	−178.8 (3)
O5—Co1—N2—C25	−75.2 (2)	C5—C4—C3—C2	−0.3 (5)
O2—Co1—N2—C25	103.90 (18)	C7—C2—C3—C4	0.8 (4)
N1—Co1—N2—C25	5.74 (18)	C1—C2—C3—C4	−178.8 (3)
O1—Co1—N2—C25	79.2 (2)	C26—N1—C15—C16	−0.9 (5)
O3—Co1—N1—C15	−138.4 (3)	Co1—N1—C15—C16	172.2 (2)
O5—Co1—N1—C15	−65.4 (3)	C25—C21—C20—C19	−2.3 (4)
N2—Co1—N1—C15	179.8 (3)	C22—C21—C20—C19	179.1 (3)
O2—Co1—N1—C15	87.7 (3)	C25—C21—C22—C23	−0.5 (4)
O1—Co1—N1—C15	28.6 (3)	C20—C21—C22—C23	178.1 (3)
O3—Co1—N1—C26	35.0 (4)	C10—C9—C14—C13	−1.2 (4)
O5—Co1—N1—C26	107.98 (19)	C8—C9—C14—C13	176.9 (3)
N2—Co1—N1—C26	−6.82 (18)	C9—C10—C11—F2	179.2 (3)
O2—Co1—N1—C26	−98.91 (19)	C9—C10—C11—C12	0.9 (5)
O1—Co1—N1—C26	−158.07 (19)	C3—C2—C7—C6	−1.1 (5)
Co1—O3—C8—O4	−7.9 (4)	C1—C2—C7—C6	178.4 (3)
Co1—O3—C8—C9	173.02 (16)	C9—C14—C13—C12	0.8 (5)
C24—N2—C25—C21	−2.5 (4)	C26—C18—C17—C16	−1.1 (5)
Co1—N2—C25—C21	175.9 (2)	C19—C18—C17—C16	180.0 (3)
C24—N2—C25—C26	177.7 (2)	C21—C22—C23—C24	−1.8 (5)
Co1—N2—C25—C26	−3.9 (3)	N2—C24—C23—C22	2.1 (5)
Co1—O2—C1—O1	2.8 (3)	C21—C20—C19—C18	−1.1 (5)
Co1—O2—C1—C2	−176.7 (2)	C26—C18—C19—C20	2.8 (4)
Co1—O1—C1—O2	−2.6 (2)	C17—C18—C19—C20	−178.2 (3)
Co1—O1—C1—C2	176.9 (2)	F1—C4—C5—C6	178.6 (3)
O2—C1—C2—C7	173.0 (3)	C3—C4—C5—C6	0.1 (5)
O1—C1—C2—C7	−6.5 (4)	C4—C5—C6—C7	−0.4 (5)
O2—C1—C2—C3	−7.4 (4)	C2—C7—C6—C5	0.9 (5)
O1—C1—C2—C3	173.1 (2)	C18—C17—C16—C15	1.4 (5)
O4—C8—C9—C14	17.7 (4)	N1—C15—C16—C17	−0.4 (5)
O3—C8—C9—C14	−163.2 (3)	F2—C11—C12—C13	−179.6 (3)
O4—C8—C9—C10	−164.2 (3)	C10—C11—C12—C13	−1.3 (5)
O3—C8—C9—C10	14.9 (4)	C14—C13—C12—C11	0.5 (5)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H1···O4	0.85 (1)	1.76 (1)	2.584 (3)	165 (3)
O5—H2···O1i	0.85 (1)	1.89 (1)	2.734 (3)	176 (3)
C22—H22···O5ii	0.93	2.52	3.332 (4)	147.
C5—H5A···F2iii	0.93	2.55	3.303 (4)	138.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H1⋯O4	0.85 (1)	1.76 (1)	2.584 (3)	165 (3)
O5—H2⋯O1i	0.85 (1)	1.89 (1)	2.734 (3)	176 (3)
C22—H22⋯O5ii	0.93	2.52	3.332 (4)	147
C5—H5A⋯F2iii	0.93	2.55	3.303 (4)	138

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