Poly[[bis­[μ-1-ethyl-6-fluoro-4-oxo-7-(1-piperazin­yl)-1,4-dihydro-1,8-naphthyridine-3-carboxyl­ato]cobalt(II)] dihydrate]

An, Z.; Wang, R.-S.

doi:10.1107/S1600536806052640

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Poly[[bis[μ-1-ethyl-6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydro-1,8-naphthyridine-3-carboxylato]cobalt(II)] dihydrate]

Z. An and R.-S. Wang

In the title compound, {[Co(C₁₅H₁₆FN₄O₃)₂]·2H₂O}_n, the Co^II atom (site symmetry $\overline{1}$ ) exists in a distorted trans-CoN₂O₄ octahedral geometry that is defined by two monodentate N-bonded and two bidentate O,O-bonded 1-ethyl-6-fluoro-4-oxo-7-(1-piperazine)-1,4-dihydro-1,8-naphthyridine-3-carboxylate (enox) monoanions. The extended two-dimensional structure is a square grid.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806052640/hb2230sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536806052640/hb2230Isup2.hkl Contains datablock I

CCDC reference: 633870

checkCIF report

Key indicators

Single-crystal X-ray study
T = 273 K
Mean (C-C) = 0.005 Å
Disorder in solvent or counterion
R factor = 0.049
wR factor = 0.140
Data-to-parameter ratio = 12.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT430_ALERT_2_B Short Inter D...A Contact  O2     ..  O2W     ..       2.79 Ang.

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.05
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.18 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.70 Ratio
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.18
PLAT302_ALERT_4_C Anion/Solvent Disorder .........................      50.00 Perc.
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) .....       >O1W
PLAT311_ALERT_2_C Isolated Disordered Oxygen Atom (No H's ?) .....       <O2W
PLAT430_ALERT_2_C Short Inter D...A Contact  O1W    ..  O2      ..       2.86 Ang.

Alert level G
FORMU01_ALERT_1_G  There is a discrepancy between the atom counts in the
            _chemical_formula_sum and _chemical_formula_moiety. This is
            usually due to the moiety formula being in the wrong format.
            Atom count from _chemical_formula_sum:   C30 H32 Co1 F2 N8 O8
            Atom count from _chemical_formula_moiety:C30 H36 Co1 F2 N8 O8

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   7 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
   0 ALERT type 5 Informative message, check

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.

Poly[[bis(µ-1-ethyl-6-fluoro-4-oxo-7-(1-piperazinyl)- 1,4-dihydro-1,8-naphtyridine-3-carboxylato)cobalt(II)] dihydrate] top

Crystal data top

[Co(C₁₅H₁₆FN₄O₃)₂]·2H₂O	F(000) = 754
M_r = 729.57	D_x = 1.470 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 7899 reflections
a = 5.9422 (4) Å	θ = 1.8–25.1°
b = 21.4433 (16) Å	µ = 0.59 mm⁻¹
c = 13.147 (1) Å	T = 273 K
β = 100.290 (2)°	Prism, pink
V = 1648.3 (2) Å³	0.32 × 0.26 × 0.18 mm
Z = 2

Data collection top

Bruker SMART CCD diffractometer	2921 independent reflections
Radiation source: fine-focus sealed tube	2204 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
ω scans	θ_max = 25.1°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→4
T_min = 0.833, T_max = 0.901	k = −25→25
8212 measured reflections	l = −13→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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0722P)² + 0.8753P] where P = (F_o² + 2F_c²)/3
2921 reflections	(Δ/σ)_max < 0.001
231 parameters	Δρ_max = 0.58 e Å⁻³
1 restraint	Δρ_min = −0.28 e Å⁻³

Special details top

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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1W	0.706 (3)	0.5030 (6)	0.0370 (8)	0.236 (6)	0.558 (8)
O2W	1.011 (4)	0.4486 (8)	0.0747 (10)	0.236 (6)	0.442 (8)
Co1	0.5000	0.5000	0.5000	0.0275 (2)
F1	−0.2027 (4)	0.24733 (11)	0.3505 (2)	0.0712 (8)
O1	0.7150 (4)	0.50170 (8)	0.39454 (17)	0.0321 (5)
O2	0.8575 (5)	0.48538 (13)	0.2537 (2)	0.0604 (8)
O3	0.3467 (4)	0.42306 (9)	0.42102 (17)	0.0353 (5)
N1	0.4900 (5)	0.32966 (12)	0.1679 (2)	0.0415 (7)
N2	0.2187 (5)	0.25384 (12)	0.1848 (2)	0.0380 (7)
N3	−0.0412 (5)	0.17533 (12)	0.1956 (2)	0.0383 (7)
N4	−0.2455 (4)	0.05952 (11)	0.1052 (2)	0.0333 (6)
H4	−0.149 (4)	0.0326 (12)	0.135 (2)	0.040*
C1	0.7238 (5)	0.47221 (14)	0.3124 (3)	0.0343 (7)
C2	0.5685 (5)	0.41691 (13)	0.2850 (2)	0.0328 (7)
C3	0.6023 (6)	0.38232 (15)	0.2021 (3)	0.0413 (8)
H3	0.7130	0.3964	0.1657	0.050*
C4	0.3197 (5)	0.30808 (14)	0.2186 (2)	0.0344 (7)
C5	0.0537 (5)	0.23036 (14)	0.2310 (2)	0.0346 (7)
C6	−0.0179 (5)	0.26604 (15)	0.3104 (3)	0.0402 (8)
C7	0.0868 (6)	0.31932 (15)	0.3452 (3)	0.0392 (8)
H7	0.0380	0.3412	0.3983	0.047*
C8	0.2695 (5)	0.34199 (13)	0.3018 (2)	0.0321 (7)
C9	0.3945 (5)	0.39759 (13)	0.3414 (2)	0.0311 (7)
C10	0.0489 (6)	0.14329 (17)	0.1137 (3)	0.0527 (10)
H10A	0.1731	0.1160	0.1439	0.063*
H10B	0.1092	0.1737	0.0709	0.063*
C11	−0.1364 (6)	0.10558 (16)	0.0480 (3)	0.0467 (9)
H11A	−0.2527	0.1339	0.0134	0.056*
H11B	−0.0711	0.0842	−0.0049	0.056*
C12	−0.3203 (6)	0.09116 (17)	0.1916 (3)	0.0476 (9)
H12A	−0.3773	0.0601	0.2344	0.057*
H12B	−0.4466	0.1186	0.1645	0.057*
C13	−0.1356 (7)	0.12932 (17)	0.2594 (3)	0.0519 (10)
H13A	−0.2002	0.1505	0.3127	0.062*
H13B	−0.0148	0.1019	0.2929	0.062*
C14	0.5407 (7)	0.29830 (19)	0.0741 (3)	0.0550 (10)
H14A	0.6999	0.3051	0.0695	0.066*
H14B	0.5174	0.2538	0.0798	0.066*
C15	0.3952 (10)	0.3215 (3)	−0.0206 (4)	0.0988 (18)
H15A	0.2373	0.3160	−0.0155	0.148*
H15B	0.4278	0.2987	−0.0791	0.148*
H15C	0.4255	0.3650	−0.0291	0.148*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1W	0.421 (19)	0.211 (11)	0.092 (6)	−0.124 (10)	0.093 (9)	0.011 (6)
O2W	0.421 (19)	0.211 (11)	0.092 (6)	−0.124 (10)	0.093 (9)	0.011 (6)
Co1	0.0323 (3)	0.0164 (3)	0.0328 (3)	0.0003 (2)	0.0035 (2)	−0.0026 (2)
F1	0.0666 (15)	0.0564 (14)	0.104 (2)	−0.0315 (12)	0.0525 (14)	−0.0349 (13)
O1	0.0342 (12)	0.0227 (11)	0.0388 (12)	−0.0041 (9)	0.0050 (9)	−0.0031 (9)
O2	0.0730 (18)	0.0590 (17)	0.0569 (17)	−0.0388 (14)	0.0322 (14)	−0.0223 (13)
O3	0.0401 (12)	0.0248 (11)	0.0423 (13)	−0.0050 (9)	0.0108 (10)	−0.0099 (10)
N1	0.0507 (17)	0.0333 (15)	0.0446 (17)	−0.0136 (13)	0.0194 (13)	−0.0142 (13)
N2	0.0449 (16)	0.0260 (13)	0.0441 (16)	−0.0097 (12)	0.0111 (13)	−0.0098 (12)
N3	0.0437 (16)	0.0285 (14)	0.0447 (17)	−0.0132 (12)	0.0133 (13)	−0.0127 (12)
N4	0.0366 (15)	0.0224 (13)	0.0397 (16)	−0.0032 (11)	0.0036 (12)	−0.0017 (11)
C1	0.0371 (17)	0.0257 (16)	0.0399 (19)	−0.0034 (14)	0.0066 (14)	−0.0038 (15)
C2	0.0411 (18)	0.0227 (15)	0.0339 (17)	−0.0072 (13)	0.0049 (13)	−0.0046 (13)
C3	0.0444 (19)	0.0357 (18)	0.046 (2)	−0.0141 (15)	0.0151 (15)	−0.0071 (16)
C4	0.0397 (18)	0.0264 (16)	0.0374 (18)	−0.0058 (14)	0.0078 (14)	−0.0055 (14)
C5	0.0356 (17)	0.0280 (16)	0.0394 (18)	−0.0049 (13)	0.0050 (14)	−0.0055 (14)
C6	0.0357 (18)	0.0345 (18)	0.054 (2)	−0.0091 (14)	0.0183 (15)	−0.0103 (16)
C7	0.0440 (19)	0.0299 (17)	0.047 (2)	−0.0053 (14)	0.0154 (16)	−0.0116 (15)
C8	0.0366 (17)	0.0220 (15)	0.0370 (17)	−0.0026 (13)	0.0052 (13)	−0.0056 (13)
C9	0.0344 (17)	0.0197 (14)	0.0383 (18)	−0.0003 (13)	0.0037 (13)	−0.0045 (13)
C10	0.056 (2)	0.042 (2)	0.064 (3)	−0.0203 (18)	0.0232 (19)	−0.0216 (19)
C11	0.063 (2)	0.0357 (19)	0.044 (2)	−0.0234 (17)	0.0179 (17)	−0.0130 (16)
C12	0.053 (2)	0.0408 (19)	0.052 (2)	−0.0186 (17)	0.0182 (17)	−0.0078 (17)
C13	0.073 (3)	0.039 (2)	0.045 (2)	−0.0166 (18)	0.0152 (19)	−0.0074 (17)
C14	0.063 (2)	0.052 (2)	0.057 (2)	−0.0185 (19)	0.0266 (19)	−0.0219 (19)
C15	0.099 (4)	0.138 (5)	0.059 (3)	0.002 (4)	0.010 (3)	−0.027 (3)

Geometric parameters (Å, º) top

Co1—O1	2.047 (2)	C2—C9	1.437 (4)
Co1—O1ⁱ	2.047 (2)	C3—H3	0.9300
Co1—O3ⁱ	2.0718 (19)	C4—C8	1.390 (4)
Co1—O3	2.0718 (19)	C5—C6	1.419 (5)
Co1—N4ⁱⁱ	2.254 (2)	C6—C7	1.342 (4)
Co1—N4ⁱⁱⁱ	2.254 (2)	C7—C8	1.400 (4)
F1—C6	1.361 (4)	C7—H7	0.9300
O1—C1	1.260 (4)	C8—C9	1.451 (4)
O2—C1	1.235 (4)	C10—C11	1.507 (5)
O3—C9	1.257 (4)	C10—H10A	0.9700
N1—C3	1.347 (4)	C10—H10B	0.9700
N1—C4	1.386 (4)	C11—H11A	0.9700
N1—C14	1.482 (4)	C11—H11B	0.9700
N2—C5	1.341 (4)	C12—C13	1.523 (5)
N2—C4	1.347 (4)	C12—H12A	0.9700
N3—C5	1.354 (4)	C12—H12B	0.9700
N3—C10	1.458 (4)	C13—H13A	0.9700
N3—C13	1.469 (4)	C13—H13B	0.9700
N4—C12	1.459 (4)	C14—C15	1.470 (7)
N4—C11	1.461 (4)	C14—H14A	0.9700
N4—Co1^iv	2.254 (2)	C14—H14B	0.9700
N4—H4	0.86 (3)	C15—H15A	0.9600
C1—C2	1.506 (4)	C15—H15B	0.9600
C2—C3	1.363 (4)	C15—H15C	0.9600

O1—Co1—O1ⁱ	180.0	F1—C6—C5	119.6 (3)
O1—Co1—O3ⁱ	93.07 (8)	C6—C7—C8	120.2 (3)
O1ⁱ—Co1—O3ⁱ	86.93 (8)	C6—C7—H7	119.9
O1—Co1—O3	86.93 (8)	C8—C7—H7	119.9
O1ⁱ—Co1—O3	93.07 (8)	C4—C8—C7	115.5 (3)
O3ⁱ—Co1—O3	180.0	C4—C8—C9	122.9 (3)
O1—Co1—N4ⁱⁱ	90.34 (9)	C7—C8—C9	121.6 (3)
O1ⁱ—Co1—N4ⁱⁱ	89.66 (9)	O3—C9—C2	126.5 (3)
O3ⁱ—Co1—N4ⁱⁱ	92.48 (9)	O3—C9—C8	118.6 (3)
O3—Co1—N4ⁱⁱ	87.52 (9)	C2—C9—C8	114.9 (3)
O1—Co1—N4ⁱⁱⁱ	89.66 (9)	N3—C10—C11	110.4 (3)
O1ⁱ—Co1—N4ⁱⁱⁱ	90.34 (9)	N3—C10—H10A	109.6
O3ⁱ—Co1—N4ⁱⁱⁱ	87.52 (9)	C11—C10—H10A	109.6
O3—Co1—N4ⁱⁱⁱ	92.48 (9)	N3—C10—H10B	109.6
N4ⁱⁱ—Co1—N4ⁱⁱⁱ	180.0	C11—C10—H10B	109.6
C1—O1—Co1	134.3 (2)	H10A—C10—H10B	108.1
C9—O3—Co1	128.22 (19)	N4—C11—C10	114.5 (3)
C3—N1—C4	118.7 (3)	N4—C11—H11A	108.6
C3—N1—C14	119.7 (3)	C10—C11—H11A	108.6
C4—N1—C14	121.5 (3)	N4—C11—H11B	108.6
C5—N2—C4	119.6 (3)	C10—C11—H11B	108.6
C5—N3—C10	118.6 (3)	H11A—C11—H11B	107.6
C5—N3—C13	124.6 (3)	N4—C12—C13	114.7 (3)
C10—N3—C13	109.5 (3)	N4—C12—H12A	108.6
C12—N4—C11	108.1 (3)	C13—C12—H12A	108.6
C12—N4—Co1^iv	118.5 (2)	N4—C12—H12B	108.6
C11—N4—Co1^iv	112.2 (2)	C13—C12—H12B	108.6
C12—N4—H4	103 (2)	H12A—C12—H12B	107.6
C11—N4—H4	111 (2)	N3—C13—C12	109.6 (3)
Co1^iv—N4—H4	103 (2)	N3—C13—H13A	109.7
O2—C1—O1	123.4 (3)	C12—C13—H13A	109.7
O2—C1—C2	117.7 (3)	N3—C13—H13B	109.7
O1—C1—C2	118.8 (3)	C12—C13—H13B	109.7
C3—C2—C9	118.6 (3)	H13A—C13—H13B	108.2
C3—C2—C1	116.6 (3)	C15—C14—N1	112.0 (4)
C9—C2—C1	124.8 (3)	C15—C14—H14A	109.2
N1—C3—C2	126.0 (3)	N1—C14—H14A	109.2
N1—C3—H3	117.0	C15—C14—H14B	109.2
C2—C3—H3	117.0	N1—C14—H14B	109.2
N2—C4—N1	116.7 (3)	H14A—C14—H14B	107.9
N2—C4—C8	124.4 (3)	C14—C15—H15A	109.5
N1—C4—C8	118.8 (3)	C14—C15—H15B	109.5
N2—C5—N3	117.7 (3)	H15A—C15—H15B	109.5
N2—C5—C6	118.0 (3)	C14—C15—H15C	109.5
N3—C5—C6	124.2 (3)	H15A—C15—H15C	109.5
C7—C6—F1	118.4 (3)	H15B—C15—H15C	109.5
C7—C6—C5	121.9 (3)

O3ⁱ—Co1—O1—C1	−172.9 (3)	N2—C5—C6—F1	172.3 (3)
O3—Co1—O1—C1	7.1 (3)	N3—C5—C6—F1	−4.6 (5)
N4ⁱⁱ—Co1—O1—C1	−80.4 (3)	F1—C6—C7—C8	−176.4 (3)
N4ⁱⁱⁱ—Co1—O1—C1	99.6 (3)	C5—C6—C7—C8	1.3 (5)
O1—Co1—O3—C9	−1.3 (2)	N2—C4—C8—C7	−5.8 (5)
O1ⁱ—Co1—O3—C9	178.7 (2)	N1—C4—C8—C7	176.4 (3)
N4ⁱⁱ—Co1—O3—C9	89.2 (3)	N2—C4—C8—C9	174.8 (3)
N4ⁱⁱⁱ—Co1—O3—C9	−90.8 (3)	N1—C4—C8—C9	−2.9 (5)
Co1—O1—C1—O2	172.1 (2)	C6—C7—C8—C4	4.0 (5)
Co1—O1—C1—C2	−9.6 (4)	C6—C7—C8—C9	−176.6 (3)
O2—C1—C2—C3	5.7 (5)	Co1—O3—C9—C2	−0.8 (4)
O1—C1—C2—C3	−172.8 (3)	Co1—O3—C9—C8	177.30 (19)
O2—C1—C2—C9	−176.1 (3)	C3—C2—C9—O3	177.7 (3)
O1—C1—C2—C9	5.4 (5)	C1—C2—C9—O3	−0.5 (5)
C4—N1—C3—C2	1.6 (5)	C3—C2—C9—C8	−0.5 (4)
C14—N1—C3—C2	178.0 (3)	C1—C2—C9—C8	−178.6 (3)
C9—C2—C3—N1	−1.7 (5)	C4—C8—C9—O3	−175.6 (3)
C1—C2—C3—N1	176.6 (3)	C7—C8—C9—O3	5.1 (4)
C5—N2—C4—N1	179.7 (3)	C4—C8—C9—C2	2.7 (4)
C5—N2—C4—C8	1.8 (5)	C7—C8—C9—C2	−176.6 (3)
C3—N1—C4—N2	−177.2 (3)	C5—N3—C10—C11	−150.2 (3)
C14—N1—C4—N2	6.5 (5)	C13—N3—C10—C11	58.3 (4)
C3—N1—C4—C8	0.8 (5)	C12—N4—C11—C10	52.1 (4)
C14—N1—C4—C8	−175.5 (3)	Co1^iv—N4—C11—C10	−175.4 (2)
C4—N2—C5—N3	−179.1 (3)	N3—C10—C11—N4	−57.3 (4)
C4—N2—C5—C6	3.8 (5)	C11—N4—C12—C13	−52.0 (4)
C10—N3—C5—N2	3.2 (5)	Co1^iv—N4—C12—C13	179.0 (2)
C13—N3—C5—N2	150.0 (3)	C5—N3—C13—C12	153.0 (3)
C10—N3—C5—C6	−179.9 (3)	C10—N3—C13—C12	−57.6 (4)
C13—N3—C5—C6	−33.0 (5)	N4—C12—C13—N3	56.5 (4)
N2—C5—C6—C7	−5.4 (5)	C3—N1—C14—C15	−89.6 (4)
N3—C5—C6—C7	177.7 (3)	C4—N1—C14—C15	86.7 (5)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x, y+1/2, −z+1/2; (iii) x+1, −y+1/2, z+1/2; (iv) −x, y−1/2, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4···O2^v	0.86 (3)	2.29 (3)	3.124 (4)	163 (2)

Symmetry code: (v) −x+1, y−1/2, −z+1/2.

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