Diaqua­bis[1-ethyl-6-fluoro-7-(4-methyl­piperazin-4-yl)-4-oxo-1,4-dihydro­quinoline-3-carboxyl­ato]cobalt(II) octa­hydrate

An, Z.; Huang, J.; Qi, W.

doi:10.1107/S1600536807030681

Diaquabis[1-ethyl-6-fluoro-7-(4-methylpiperazin-4-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylato]cobalt(II) octahydrate

In the title compound, [Co(C₁₇H₁₉FN₃O₃)₂(H₂O)₂]·8H₂O, the Co^II atom (site symmetry $\overline{1}$ ) exhibits a distorted octahedral geometry that is defined by two bidentate O,O-bonded 1-ethyl-6-fluoro-7-(4-methylpiperazin-4-yl)-4-oxo-1,4-dihydroquinoline-3-carboxylate (pef) monoanions and two water molecules. A network of O—H

O and O—H

N hydrogen bonds help to establish the crystal packing.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807030681/hb2455sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807030681/hb2455Isup2.hkl Contains datablock I

CCDC reference: 654833

checkCIF report

Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.003 Å
R factor = 0.034
wR factor = 0.103
Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT153_ALERT_1_C The su's on the Cell Axes   are Equal (x 100000)        500 Ang.
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)        500 Deg.
PLAT245_ALERT_2_C U(iso) H4W1    Smaller than U(eq) O4W     by ...       0.01 AngSq
PLAT245_ALERT_2_C U(iso) H4W2    Smaller than U(eq) O4W     by ...       0.01 AngSq
PLAT417_ALERT_2_C Short Inter D-H..H-D       H4W1   ..  H1W1    ..       2.13 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........         10
PLAT735_ALERT_1_C D-H     Calc   0.840(19), Rep    0.840(9) ......       2.11 su-Ra
              O2W  -H6#     1.555   1.555
PLAT735_ALERT_1_C D-H     Calc     0.84(2), Rep    0.840(9) ......       2.22 su-Ra
              O2W  -H7#     1.555   1.555

Alert level G
PLAT794_ALERT_5_G Check Predicted Bond Valency for Co1         (9)       1.60
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......         15

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   8 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   1 ALERT type 5 Informative message, check

Comment top

Pefloxacin (Hpef, 1-ethyl-6-fluoro-7-(4-methylpiperazin-1-yl)-4-oxoquinoline-3-carboxylic acid) is member of a class of quinolones used to treat infections (Mizuki et al., 1996). The silver(I) derivative of pefloxacin have been reported (Baenziger et al., 1986). The title cobalt(II) derivative, (I), is reported here.

The Co^II atom (site symmetry 1) in (I) exhibits a distorted octahedral geometry, defined by six oxygen atoms from two pefloxacin ligands and two water (Table 1, Fig. 1). The component species in (I) are linked by the O—H···O and O—H···N hydrogen bonds involving all the potential donors, generating a three-dimensional supramolecular network.

Related literature top

For a silver complex of the same ligand, see: Baenziger et al. (1986). For background on the medicial uses of the free ligand, see Mizuki et al. (1996).

Experimental top

A mixture of Co(CH₃COO)₂·4H₂O (0.062 g, 0.25 mmol), Hpef (0.17 g, 0.5 mmol) and water (12 ml) was stirred for 30 min in air. The mixture was then transferred to a 23 ml Teflon-lined hydrothermal bomb. The bomb was heated to 433 K for 72 h under autogenous pressure. Pink blocks of (I) suitable for X-ray analysis were obtained from the reaction mixture upon cooling.

Structure description top

For a silver complex of the same ligand, see: Baenziger et al. (1986). For background on the medicial uses of the free ligand, see Mizuki et al. (1996).

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

Figures top

Fig. 1. The molecular structure of (I), showing 50% displacement ellipsoids (arbitrary spheres for the H atoms). Symmetry code: (i) 1 - x, 1 - y, -z.

Diaquabis[1-ethyl-6-fluoro-7-(4-methylpiperazin-4-yl)-4-oxo-1,4- dihydroquinoline-3-carboxylato]cobalt(II) octahydrate top

Crystal data top

[Co(C₁₇H₁₉FN₃O₃)₂(H₂O)₂]·8H₂O	Z = 1
M_r = 903.79	F(000) = 477
Triclinic, P1	D_x = 1.403 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 8.889 (5) Å	Cell parameters from 2882 reflections
b = 10.231 (5) Å	θ = 1.7–25.0°
c = 12.911 (5) Å	µ = 0.48 mm⁻¹
α = 73.287 (5)°	T = 295 K
β = 72.040 (5)°	Block, pink
γ = 85.603 (5)°	0.34 × 0.26 × 0.17 mm
V = 1069.7 (9) Å³

Data collection top

Bruker SMART CCD diffractometer	3756 independent reflections
Radiation source: fine-focus sealed tube	3380 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.015
ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→10
T_min = 0.853, T_max = 0.922	k = −12→11
5428 measured reflections	l = −15→15

Refinement top

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)] = 0.034	Hydrogen site location: difmap and geom
wR(F²) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.055P)² + 0.3439P] where P = (F_o² + 2F_c²)/3
3756 reflections	(Δ/σ)_max < 0.001
300 parameters	Δρ_max = 0.48 e Å⁻³
15 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

[Co(C₁₇H₁₉FN₃O₃)₂(H₂O)₂]·8H₂O	γ = 85.603 (5)°
M_r = 903.79	V = 1069.7 (9) Å³
Triclinic, P1	Z = 1
a = 8.889 (5) Å	Mo Kα radiation
b = 10.231 (5) Å	µ = 0.48 mm⁻¹
c = 12.911 (5) Å	T = 295 K
α = 73.287 (5)°	0.34 × 0.26 × 0.17 mm
β = 72.040 (5)°

Data collection top

Bruker SMART CCD diffractometer	3756 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3380 reflections with I > 2σ(I)
T_min = 0.853, T_max = 0.922	R_int = 0.015
5428 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	15 restraints
wR(F²) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.48 e Å⁻³
3756 reflections	Δρ_min = −0.37 e Å⁻³
300 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Co1	0.5000	0.5000	0.0000	0.02908 (14)
C1	0.5131 (2)	0.2447 (2)	0.19334 (17)	0.0301 (4)
C2	0.4572 (2)	0.3295 (2)	0.27595 (16)	0.0283 (4)
C3	0.4449 (2)	0.2636 (2)	0.38738 (17)	0.0307 (4)
H3	0.4774	0.1733	0.4036	0.037*
C4	0.3317 (2)	0.45088 (19)	0.45597 (16)	0.0273 (4)
C5	0.2592 (2)	0.5077 (2)	0.54588 (16)	0.0296 (4)
H5	0.2524	0.4571	0.6197	0.036*
C6	0.1977 (2)	0.6377 (2)	0.52631 (16)	0.0296 (4)
C7	0.2172 (3)	0.7112 (2)	0.41160 (18)	0.0347 (5)
C8	0.2845 (2)	0.6589 (2)	0.32356 (17)	0.0328 (4)
H8	0.2920	0.7108	0.2500	0.039*
C9	0.3434 (2)	0.52531 (19)	0.34378 (16)	0.0273 (4)
C10	0.4125 (2)	0.4693 (2)	0.24821 (16)	0.0274 (4)
C11	0.3830 (3)	0.2310 (2)	0.58984 (17)	0.0361 (5)
H11A	0.4012	0.2874	0.6338	0.043*
H11B	0.4663	0.1640	0.5843	0.043*
C12	0.2252 (4)	0.1581 (3)	0.6505 (2)	0.0605 (7)
H12A	0.1427	0.2241	0.6585	0.091*
H12B	0.2258	0.1022	0.7242	0.091*
H12C	0.2069	0.1018	0.6075	0.091*
C13	0.1324 (2)	0.6346 (2)	0.72586 (17)	0.0333 (4)
H13A	0.2394	0.6045	0.7229	0.040*
H13B	0.0627	0.5552	0.7595	0.040*
C14	0.0828 (3)	0.7342 (2)	0.79736 (18)	0.0399 (5)
H14A	0.0900	0.6906	0.8730	0.048*
H14B	0.1540	0.8127	0.7642	0.048*
C15	−0.0391 (3)	0.7464 (2)	0.61697 (19)	0.0386 (5)
H15A	−0.1096	0.6675	0.6488	0.046*
H15B	−0.0455	0.7914	0.5413	0.046*
C16	−0.0896 (3)	0.8433 (2)	0.68983 (19)	0.0393 (5)
H16A	−0.0223	0.9242	0.6556	0.047*
H16B	−0.1975	0.8713	0.6937	0.047*
C17	−0.1262 (4)	0.8792 (3)	0.8708 (2)	0.0576 (7)
H17A	−0.0605	0.9595	0.8328	0.086*
H17B	−0.1137	0.8398	0.9446	0.086*
H17C	−0.2348	0.9033	0.8782	0.086*
F1	0.16971 (19)	0.84283 (13)	0.38897 (11)	0.0547 (4)
N1	0.3904 (2)	0.31782 (16)	0.47450 (13)	0.0301 (4)
N2	0.12440 (19)	0.70204 (17)	0.61093 (14)	0.0304 (4)
N3	−0.0797 (2)	0.77955 (18)	0.80430 (15)	0.0380 (4)
O1	0.53493 (18)	0.30345 (14)	0.08824 (12)	0.0374 (3)
O2	0.5324 (2)	0.12126 (15)	0.23227 (13)	0.0464 (4)
O3	0.42376 (18)	0.54564 (14)	0.14985 (11)	0.0358 (3)
O1W	0.6676 (2)	0.14217 (17)	0.94617 (14)	0.0480 (4)
O2W	0.7499 (2)	0.66234 (18)	0.16054 (15)	0.0491 (4)
O3W	0.5779 (2)	0.90613 (18)	0.13899 (16)	0.0523 (4)
O4W	0.9208 (2)	0.3290 (2)	0.9021 (2)	0.0768 (7)
O5W	0.74297 (18)	0.55369 (16)	−0.02246 (13)	0.0414 (4)
H4W1	0.867 (2)	0.263 (2)	0.904 (2)	0.062*
H3W1	0.493 (2)	0.889 (3)	0.128 (2)	0.062*
H3W2	0.561 (3)	0.969 (2)	0.172 (2)	0.062*
H1W1	0.628 (3)	0.1962 (19)	0.9860 (18)	0.062*
H1W2	0.680 (3)	0.0644 (14)	0.9890 (18)	0.062*
H2W1	0.708 (3)	0.7396 (15)	0.151 (2)	0.062*
H2W2	0.752 (3)	0.627 (2)	0.1088 (18)	0.062*
H5W1	0.781 (3)	0.6243 (15)	−0.0782 (16)	0.062*
H5W2	0.792 (3)	0.4842 (15)	−0.041 (2)	0.062*
H4W2	1.0178 (12)	0.314 (2)	0.884 (2)	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0346 (2)	0.0295 (2)	0.0213 (2)	0.00173 (15)	−0.00322 (15)	−0.01031 (15)
C1	0.0304 (10)	0.0307 (11)	0.0299 (11)	0.0019 (8)	−0.0058 (8)	−0.0135 (9)
C2	0.0277 (10)	0.0298 (10)	0.0279 (10)	0.0008 (8)	−0.0054 (8)	−0.0119 (8)
C3	0.0336 (11)	0.0263 (10)	0.0323 (11)	0.0036 (8)	−0.0083 (9)	−0.0110 (8)
C4	0.0281 (10)	0.0274 (10)	0.0265 (10)	−0.0013 (8)	−0.0063 (8)	−0.0093 (8)
C5	0.0332 (11)	0.0311 (10)	0.0228 (9)	−0.0004 (8)	−0.0051 (8)	−0.0083 (8)
C6	0.0300 (10)	0.0328 (10)	0.0257 (10)	−0.0007 (8)	−0.0041 (8)	−0.0119 (8)
C7	0.0434 (12)	0.0265 (10)	0.0310 (11)	0.0065 (9)	−0.0073 (9)	−0.0091 (8)
C8	0.0412 (12)	0.0307 (11)	0.0226 (10)	0.0004 (9)	−0.0057 (8)	−0.0058 (8)
C9	0.0291 (10)	0.0272 (10)	0.0245 (10)	−0.0018 (8)	−0.0039 (8)	−0.0093 (8)
C10	0.0263 (10)	0.0306 (10)	0.0248 (10)	−0.0028 (8)	−0.0044 (8)	−0.0095 (8)
C11	0.0495 (13)	0.0325 (11)	0.0284 (11)	0.0055 (9)	−0.0165 (9)	−0.0078 (9)
C12	0.0781 (19)	0.0554 (16)	0.0415 (14)	−0.0244 (14)	−0.0235 (14)	0.0088 (12)
C13	0.0349 (11)	0.0365 (11)	0.0264 (10)	0.0047 (9)	−0.0061 (8)	−0.0103 (8)
C14	0.0455 (13)	0.0460 (13)	0.0294 (11)	−0.0001 (10)	−0.0080 (10)	−0.0158 (10)
C15	0.0357 (11)	0.0454 (13)	0.0379 (12)	0.0105 (10)	−0.0116 (9)	−0.0185 (10)
C16	0.0369 (12)	0.0361 (12)	0.0402 (12)	0.0077 (9)	−0.0033 (9)	−0.0139 (10)
C17	0.0745 (18)	0.0459 (14)	0.0454 (14)	0.0048 (13)	0.0045 (13)	−0.0272 (12)
F1	0.0874 (11)	0.0312 (7)	0.0354 (7)	0.0207 (7)	−0.0088 (7)	−0.0094 (6)
N1	0.0369 (9)	0.0278 (8)	0.0248 (8)	0.0038 (7)	−0.0082 (7)	−0.0082 (7)
N2	0.0307 (9)	0.0346 (9)	0.0254 (8)	0.0057 (7)	−0.0046 (7)	−0.0129 (7)
N3	0.0420 (10)	0.0338 (9)	0.0326 (9)	0.0018 (8)	0.0026 (8)	−0.0157 (8)
O1	0.0512 (9)	0.0331 (8)	0.0268 (8)	0.0062 (7)	−0.0065 (6)	−0.0137 (6)
O2	0.0740 (11)	0.0291 (8)	0.0368 (8)	0.0121 (7)	−0.0158 (8)	−0.0143 (7)
O3	0.0518 (9)	0.0302 (7)	0.0214 (7)	0.0047 (6)	−0.0051 (6)	−0.0086 (6)
O1W	0.0664 (11)	0.0362 (9)	0.0383 (9)	0.0063 (8)	−0.0065 (8)	−0.0170 (7)
O2W	0.0560 (11)	0.0459 (10)	0.0481 (10)	0.0083 (8)	−0.0200 (8)	−0.0141 (8)
O3W	0.0652 (12)	0.0428 (10)	0.0590 (11)	0.0121 (8)	−0.0257 (9)	−0.0248 (8)
O4W	0.0406 (10)	0.0666 (14)	0.1171 (19)	−0.0018 (9)	−0.0131 (12)	−0.0269 (13)
O5W	0.0394 (9)	0.0383 (8)	0.0421 (9)	−0.0033 (7)	−0.0068 (7)	−0.0096 (7)

Geometric parameters (Å, º) top

Co1—O3ⁱ	2.0206 (15)	C12—H12B	0.9600
Co1—O3	2.0206 (15)	C12—H12C	0.9600
Co1—O1	2.0598 (16)	C13—N2	1.467 (3)
Co1—O1ⁱ	2.0598 (16)	C13—C14	1.519 (3)
Co1—O5W	2.180 (2)	C13—H13A	0.9700
Co1—O5Wⁱ	2.180 (2)	C13—H13B	0.9700
C1—O2	1.237 (3)	C14—N3	1.467 (3)
C1—O1	1.275 (2)	C14—H14A	0.9700
C1—C2	1.509 (3)	C14—H14B	0.9700
C2—C3	1.376 (3)	C15—N2	1.475 (3)
C2—C10	1.428 (3)	C15—C16	1.509 (3)
C3—N1	1.338 (3)	C15—H15A	0.9700
C3—H3	0.9300	C15—H15B	0.9700
C4—N1	1.401 (3)	C16—N3	1.461 (3)
C4—C5	1.403 (3)	C16—H16A	0.9700
C4—C9	1.405 (3)	C16—H16B	0.9700
C5—C6	1.383 (3)	C17—N3	1.472 (3)
C5—H5	0.9300	C17—H17A	0.9600
C6—N2	1.400 (2)	C17—H17B	0.9600
C6—C7	1.418 (3)	C17—H17C	0.9600
C7—C8	1.348 (3)	O1W—H1W1	0.846 (10)
C7—F1	1.356 (2)	O1W—H1W2	0.849 (10)
C8—C9	1.407 (3)	O2W—H2W1	0.840 (19)
C8—H8	0.9300	O2W—H2W2	0.84 (2)
C9—C10	1.454 (3)	O3W—H3W1	0.848 (10)
C10—O3	1.263 (2)	O3W—H3W2	0.851 (10)
C11—N1	1.483 (3)	O4W—H4W1	0.844 (10)
C11—C12	1.511 (3)	O4W—H4W2	0.835 (10)
C11—H11A	0.9700	O5W—H5W1	0.862 (10)
C11—H11B	0.9700	O5W—H5W2	0.856 (10)
C12—H12A	0.9600

O3ⁱ—Co1—O3	180.0	H12A—C12—H12B	109.5
O3ⁱ—Co1—O1	92.09 (6)	C11—C12—H12C	109.5
O3—Co1—O1	87.91 (6)	H12A—C12—H12C	109.5
O3ⁱ—Co1—O1ⁱ	87.91 (6)	H12B—C12—H12C	109.5
O3—Co1—O1ⁱ	92.09 (6)	N2—C13—C14	109.25 (17)
O1—Co1—O1ⁱ	180.0	N2—C13—H13A	109.8
O3ⁱ—Co1—O5W	88.65 (6)	C14—C13—H13A	109.8
O3—Co1—O5W	91.35 (6)	N2—C13—H13B	109.8
O1—Co1—O5W	90.07 (6)	C14—C13—H13B	109.8
O1ⁱ—Co1—O5W	89.93 (6)	H13A—C13—H13B	108.3
O3ⁱ—Co1—O5Wⁱ	91.35 (6)	N3—C14—C13	110.74 (17)
O3—Co1—O5Wⁱ	88.65 (6)	N3—C14—H14A	109.5
O1—Co1—O5Wⁱ	89.93 (6)	C13—C14—H14A	109.5
O1ⁱ—Co1—O5Wⁱ	90.07 (6)	N3—C14—H14B	109.5
O5W—Co1—O5Wⁱ	180.0	C13—C14—H14B	109.5
O2—C1—O1	123.93 (18)	H14A—C14—H14B	108.1
O2—C1—C2	117.69 (18)	N2—C15—C16	110.02 (18)
O1—C1—C2	118.37 (17)	N2—C15—H15A	109.7
C3—C2—C10	118.28 (17)	C16—C15—H15A	109.7
C3—C2—C1	116.25 (17)	N2—C15—H15B	109.7
C10—C2—C1	125.44 (17)	C16—C15—H15B	109.7
N1—C3—C2	125.78 (18)	H15A—C15—H15B	108.2
N1—C3—H3	117.1	N3—C16—C15	111.24 (18)
C2—C3—H3	117.1	N3—C16—H16A	109.4
N1—C4—C5	121.73 (17)	C15—C16—H16A	109.4
N1—C4—C9	117.70 (17)	N3—C16—H16B	109.4
C5—C4—C9	120.55 (18)	C15—C16—H16B	109.4
C6—C5—C4	120.95 (18)	H16A—C16—H16B	108.0
C6—C5—H5	119.5	N3—C17—H17A	109.5
C4—C5—H5	119.5	N3—C17—H17B	109.5
C5—C6—N2	124.57 (18)	H17A—C17—H17B	109.5
C5—C6—C7	116.71 (17)	N3—C17—H17C	109.5
N2—C6—C7	118.67 (18)	H17A—C17—H17C	109.5
C8—C7—F1	118.16 (18)	H17B—C17—H17C	109.5
C8—C7—C6	123.67 (18)	C3—N1—C4	119.52 (16)
F1—C7—C6	118.13 (17)	C3—N1—C11	118.58 (16)
C7—C8—C9	119.53 (18)	C4—N1—C11	121.75 (16)
C7—C8—H8	120.2	C6—N2—C13	117.51 (16)
C9—C8—H8	120.2	C6—N2—C15	115.44 (16)
C4—C9—C8	118.51 (17)	C13—N2—C15	109.06 (16)
C4—C9—C10	122.62 (17)	C16—N3—C14	109.00 (16)
C8—C9—C10	118.87 (17)	C16—N3—C17	109.03 (18)
O3—C10—C2	126.05 (18)	C14—N3—C17	110.79 (19)
O3—C10—C9	118.16 (18)	C1—O1—Co1	132.96 (12)
C2—C10—C9	115.76 (17)	C10—O3—Co1	129.04 (13)
N1—C11—C12	112.06 (18)	H1W1—O1W—H1W2	109.4 (15)
N1—C11—H11A	109.2	H2W1—O2W—H2W2	112.1 (16)
C12—C11—H11A	109.2	H3W1—O3W—H3W2	109.2 (15)
N1—C11—H11B	109.2	H4W1—O4W—H4W2	112.0 (16)
C12—C11—H11B	109.2	Co1—O5W—H5W1	114.6 (19)
H11A—C11—H11B	107.9	Co1—O5W—H5W2	100.6 (18)
C11—C12—H12A	109.5	H5W1—O5W—H5W2	107.0 (15)
C11—C12—H12B	109.5

O2—C1—C2—C3	5.2 (3)	C2—C3—N1—C4	3.5 (3)
O1—C1—C2—C3	−176.05 (18)	C2—C3—N1—C11	179.04 (19)
O2—C1—C2—C10	−172.9 (2)	C5—C4—N1—C3	173.72 (18)
O1—C1—C2—C10	5.9 (3)	C9—C4—N1—C3	−4.4 (3)
C10—C2—C3—N1	1.8 (3)	C5—C4—N1—C11	−1.7 (3)
C1—C2—C3—N1	−176.44 (18)	C9—C4—N1—C11	−179.82 (17)
N1—C4—C5—C6	−178.05 (18)	C12—C11—N1—C3	−91.1 (2)
C9—C4—C5—C6	0.1 (3)	C12—C11—N1—C4	84.3 (2)
C4—C5—C6—N2	−179.66 (18)	C5—C6—N2—C13	8.6 (3)
C4—C5—C6—C7	−2.3 (3)	C7—C6—N2—C13	−168.65 (18)
C5—C6—C7—C8	3.2 (3)	C5—C6—N2—C15	−122.3 (2)
N2—C6—C7—C8	−179.29 (19)	C7—C6—N2—C15	60.4 (2)
C5—C6—C7—F1	−174.77 (18)	C14—C13—N2—C6	166.40 (17)
N2—C6—C7—F1	2.7 (3)	C14—C13—N2—C15	−59.8 (2)
F1—C7—C8—C9	176.32 (19)	C16—C15—N2—C6	−165.98 (18)
C6—C7—C8—C9	−1.7 (3)	C16—C15—N2—C13	59.2 (2)
N1—C4—C9—C8	179.74 (17)	C15—C16—N3—C14	57.5 (2)
C5—C4—C9—C8	1.6 (3)	C15—C16—N3—C17	178.60 (19)
N1—C4—C9—C10	0.4 (3)	C13—C14—N3—C16	−58.4 (2)
C5—C4—C9—C10	−177.81 (17)	C13—C14—N3—C17	−178.33 (19)
C7—C8—C9—C4	−0.8 (3)	O2—C1—O1—Co1	175.48 (15)
C7—C8—C9—C10	178.62 (19)	C2—C1—O1—Co1	−3.2 (3)
C3—C2—C10—O3	176.41 (18)	O3ⁱ—Co1—O1—C1	−179.59 (18)
C1—C2—C10—O3	−5.5 (3)	O3—Co1—O1—C1	0.41 (18)
C3—C2—C10—C9	−5.5 (3)	O5W—Co1—O1—C1	91.75 (19)
C1—C2—C10—C9	172.50 (17)	O5Wⁱ—Co1—O1—C1	−88.25 (19)
C4—C9—C10—O3	−177.22 (18)	C2—C10—O3—Co1	2.1 (3)
C8—C9—C10—O3	3.4 (3)	C9—C10—O3—Co1	−175.93 (13)
C4—C9—C10—C2	4.6 (3)	O1—Co1—O3—C10	0.37 (17)
C8—C9—C10—C2	−174.79 (18)	O1ⁱ—Co1—O3—C10	−179.63 (17)
N2—C13—C14—N3	60.3 (2)	O5W—Co1—O3—C10	−89.65 (17)
N2—C15—C16—N3	−58.6 (2)	O5Wⁱ—Co1—O3—C10	90.35 (17)

Symmetry code: (i) −x+1, −y+1, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4W—H4W1···O1W	0.84 (1)	2.08 (1)	2.879 (3)	157 (2)
O3W—H3W1···O1Wⁱⁱ	0.85 (1)	2.04 (1)	2.859 (3)	164 (3)
O3W—H3W2···O2ⁱⁱⁱ	0.85 (1)	1.90 (1)	2.747 (2)	174 (3)
O1W—H1W1···O1^iv	0.85 (1)	1.91 (1)	2.754 (2)	175 (2)
O1W—H1W2···O3W^v	0.85 (1)	2.13 (2)	2.877 (3)	147 (2)
O2W—H2W1···O3W	0.84 (1)	1.98 (1)	2.813 (3)	171 (3)
O2W—H2W2···O5W	0.84 (1)	2.07 (1)	2.904 (3)	175 (2)
O5W—H5W1···N3^vi	0.86 (1)	2.03 (1)	2.870 (3)	165 (3)
O5W—H5W2···O4W^vii	0.86 (1)	2.06 (1)	2.918 (3)	175 (2)
O4W—H4W2···O2W^viii	0.84 (1)	1.98 (1)	2.787 (3)	162 (2)

Symmetry codes: (ii) −x+1, −y+1, −z+1; (iii) x, y+1, z; (iv) x, y, z+1; (v) x, y−1, z+1; (vi) x+1, y, z−1; (vii) x, y, z−1; (viii) −x+2, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	[Co(C₁₇H₁₉FN₃O₃)₂(H₂O)₂]·8H₂O
M_r	903.79
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	8.889 (5), 10.231 (5), 12.911 (5)
α, β, γ (°)	73.287 (5), 72.040 (5), 85.603 (5)
V (Å³)	1069.7 (9)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.48
Crystal size (mm)	0.34 × 0.26 × 0.17

Data collection
Diffractometer	Bruker SMART CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.853, 0.922
No. of measured, independent and observed [I > 2σ(I)] reflections	5428, 3756, 3380
R_int	0.015
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.103, 1.10
No. of reflections	3756
No. of parameters	300
No. of restraints	15
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.48, −0.37

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), SHELXTL.

Selected bond lengths (Å) top

Co1—O3	2.0206 (15)	Co1—O5W	2.180 (2)
Co1—O1	2.0598 (16)