Poly[[bis­[μ₂-1-cyclo­propyl-6-fluoro-4-oxo-7-(1-piperazin­yl)-1,4-dihydro­quinoline-3-carboxyl­ato]copper(II)] dihydrate]

In the title compound, {[Cu(C₁₇H₁₇FN₃O₃)₂]·2H₂O}_n, the Cu^II atom exists in a distorted trans-CuN₂O₄ octa­hedral geometry that is defined by two monodentate N-bonded and two bidentate O,O-bonded 1-cyclo­propyl-6-fluoro-4-oxo-7-(1-piperazinyl)-1,4-dihydro­quinoline-3-carboxylate (cf) mono­anions. The extended two-dimensional structure is a rectangular grid. The Cu atom lies on a centre of inversion.

Key indicators

• Single-crystal X-ray study
• T = 295 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.038
• wR factor = 0.104
• Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D       H1W2   ..  H1W2    ..       1.53 Ang.

Alert level C
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.62 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for        C12
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.11
PLAT411_ALERT_2_C Short Inter H...H Contact  H5     ..  H15A    ..       2.14 Ang.
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          3
            N3  -CU1 -N3  -C15     9.00  0.00   3.565   1.555   1.555   1.555
PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          8
            N3  -CU1 -N3  -C16    15.00  0.00   3.565   1.555   1.555   1.555
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          2

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

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

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; 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[µ₂-1-cyclopropyl-6-fluoro-4-oxo-7-(1-piperazinyl)-1,4- dihydroquinoline-3-carboxylato]copper(II)] dihydrate]

Crystal data

[Cu(C17H17FN3O3)2]·2H2O	F(000) = 790
Mr = 760.24	Dx = 1.538 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 8399 reflections
a = 5.7108 (3) Å	θ = 1.8–25.5°
b = 21.8212 (11) Å	µ = 0.74 mm^−1
c = 13.4418 (7) Å	T = 295 K
β = 101.527 (1)°	Prism, blue
V = 1641.28 (15) Å^3	0.32 × 0.26 × 0.18 mm
Z = 2

Data collection

Bruker SMART CCD area-detector diffractometer	3045 independent reflections
Radiation source: fine-focus sealed tube	2409 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
ω scans	θmax = 25.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −6→6
Tmin = 0.798, Tmax = 0.878	k = −26→25
8429 measured reflections	l = −13→16

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.104	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.046P)^2 + 1.495P] where P = (Fo^2 + 2Fc^2)/3
3045 reflections	(Δ/σ)max < 0.001
236 parameters	Δρmax = 0.62 e Å^−3
1 restraint	Δρmin = −0.34 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
O1W	1.2772 (14)	−0.01779 (19)	0.0391 (3)	0.202 (3)
H1W1	1.3009	−0.0147	0.1034	0.303*
H1W2	1.1325	−0.0084	0.0150	0.303*
Cu1	0.0000	0.5000	0.0000	0.01978 (15)
F1	0.2800 (3)	0.25267 (7)	0.31838 (14)	0.0402 (5)
O1	1.2072 (3)	−0.00596 (8)	0.39700 (14)	0.0247 (4)
O2	1.3233 (4)	−0.00601 (9)	0.25049 (16)	0.0420 (6)
O3	0.7916 (3)	0.07032 (8)	0.39401 (14)	0.0285 (4)
N1	0.9877 (4)	0.15130 (10)	0.14769 (17)	0.0255 (5)
N2	0.4153 (4)	0.31567 (10)	0.15909 (17)	0.0251 (5)
N3	0.2450 (4)	0.43606 (10)	0.08009 (17)	0.0231 (5)
C1	1.2000 (5)	0.01511 (11)	0.3085 (2)	0.0238 (6)
C2	1.0439 (5)	0.06976 (11)	0.27158 (19)	0.0221 (6)
C3	0.8572 (5)	0.09301 (11)	0.31890 (19)	0.0225 (6)
C4	0.7445 (5)	0.14950 (11)	0.27407 (19)	0.0216 (6)
C5	0.5651 (5)	0.17687 (11)	0.3155 (2)	0.0247 (6)
H5	0.5137	0.1579	0.3693	0.030*
C6	0.4646 (5)	0.23053 (12)	0.2787 (2)	0.0249 (6)
C7	0.5340 (5)	0.26263 (11)	0.19832 (19)	0.0228 (6)
C8	0.7097 (5)	0.23480 (12)	0.1561 (2)	0.0255 (6)
H8	0.7609	0.2541	0.1026	0.031*
C9	0.8124 (5)	0.17873 (11)	0.1913 (2)	0.0232 (6)
C10	1.0951 (5)	0.10011 (12)	0.1891 (2)	0.0247 (6)
H10	1.2148	0.0837	0.1593	0.030*
C11	1.0656 (5)	0.18174 (13)	0.0634 (2)	0.0314 (7)
H11	1.1443	0.2214	0.0799	0.038*
C12	1.1554 (7)	0.14560 (17)	−0.0137 (3)	0.0564 (10)
H12A	1.1562	0.1013	−0.0072	0.068*
H12B	1.2869	0.1624	−0.0408	0.068*
C13	0.9197 (7)	0.17684 (17)	−0.0406 (2)	0.0504 (9)
H13A	0.9079	0.2127	−0.0839	0.060*
H13B	0.7771	0.1516	−0.0503	0.060*
C14	0.4684 (6)	0.33860 (13)	0.0648 (2)	0.0379 (8)
H14A	0.4758	0.3047	0.0189	0.045*
H14B	0.6228	0.3588	0.0782	0.045*
C15	0.2774 (6)	0.38343 (13)	0.0159 (2)	0.0365 (7)
H15A	0.3180	0.3986	−0.0464	0.044*
H15B	0.1267	0.3617	−0.0023	0.044*
C16	0.2076 (5)	0.41273 (12)	0.1784 (2)	0.0298 (6)
H16A	0.0522	0.3931	0.1686	0.036*
H16B	0.2062	0.4471	0.2241	0.036*
C17	0.3972 (5)	0.36712 (12)	0.2281 (2)	0.0303 (7)
H17A	0.5505	0.3877	0.2458	0.036*
H17B	0.3564	0.3516	0.2901	0.036*
H3N	0.378 (3)	0.4564 (13)	0.091 (3)	0.049 (10)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1W	0.453 (10)	0.082 (3)	0.070 (3)	0.005 (4)	0.050 (4)	−0.002 (2)
Cu1	0.0278 (3)	0.0126 (2)	0.0188 (2)	0.00155 (18)	0.00446 (17)	−0.00132 (18)
F1	0.0487 (11)	0.0318 (9)	0.0486 (11)	0.0147 (8)	0.0300 (9)	0.0101 (8)
O1	0.0313 (10)	0.0196 (9)	0.0223 (9)	0.0014 (8)	0.0032 (8)	0.0044 (8)
O2	0.0574 (14)	0.0383 (12)	0.0356 (12)	0.0239 (11)	0.0216 (11)	0.0110 (10)
O3	0.0359 (11)	0.0227 (10)	0.0294 (10)	0.0023 (8)	0.0127 (9)	0.0102 (8)
N1	0.0307 (13)	0.0223 (12)	0.0264 (12)	0.0050 (9)	0.0127 (10)	0.0068 (9)
N2	0.0378 (13)	0.0176 (11)	0.0211 (11)	0.0076 (9)	0.0090 (10)	0.0028 (9)
N3	0.0288 (13)	0.0149 (11)	0.0253 (12)	0.0021 (9)	0.0050 (10)	0.0003 (9)
C1	0.0308 (15)	0.0179 (13)	0.0228 (14)	−0.0007 (10)	0.0058 (12)	0.0020 (10)
C2	0.0274 (14)	0.0165 (13)	0.0215 (13)	−0.0002 (10)	0.0027 (11)	0.0019 (10)
C3	0.0281 (14)	0.0156 (12)	0.0229 (13)	−0.0027 (10)	0.0028 (11)	0.0023 (10)
C4	0.0275 (14)	0.0179 (13)	0.0199 (13)	0.0006 (10)	0.0057 (11)	0.0022 (10)
C5	0.0315 (15)	0.0207 (13)	0.0241 (14)	−0.0014 (11)	0.0107 (12)	0.0037 (11)
C6	0.0273 (14)	0.0219 (13)	0.0284 (14)	0.0040 (11)	0.0124 (12)	0.0010 (11)
C7	0.0269 (14)	0.0190 (13)	0.0222 (14)	0.0017 (11)	0.0042 (11)	0.0019 (11)
C8	0.0339 (15)	0.0213 (13)	0.0231 (14)	0.0035 (11)	0.0097 (12)	0.0071 (11)
C9	0.0289 (15)	0.0206 (13)	0.0211 (13)	0.0023 (11)	0.0071 (11)	0.0023 (10)
C10	0.0282 (14)	0.0218 (13)	0.0250 (14)	0.0061 (11)	0.0073 (11)	0.0036 (11)
C11	0.0355 (16)	0.0325 (16)	0.0296 (15)	0.0038 (12)	0.0147 (13)	0.0115 (13)
C12	0.087 (3)	0.049 (2)	0.046 (2)	0.025 (2)	0.043 (2)	0.0183 (17)
C13	0.060 (2)	0.063 (2)	0.0283 (17)	0.0018 (19)	0.0090 (16)	0.0121 (16)
C14	0.058 (2)	0.0315 (16)	0.0297 (15)	0.0231 (15)	0.0222 (15)	0.0114 (13)
C15	0.064 (2)	0.0253 (15)	0.0218 (14)	0.0209 (14)	0.0125 (14)	0.0028 (12)
C16	0.0427 (17)	0.0225 (14)	0.0253 (14)	0.0087 (12)	0.0098 (13)	0.0005 (11)
C17	0.0468 (18)	0.0202 (14)	0.0232 (14)	0.0046 (12)	0.0054 (13)	−0.0007 (11)

Geometric parameters (Å, º)

O1W—H1W1	0.8500	C4—C5	1.394 (4)
O1W—H1W2	0.8500	C4—C9	1.403 (3)
Cu1—O1^i	1.9971 (18)	C5—C6	1.353 (4)
Cu1—O1^ii	1.9971 (18)	C5—H5	0.9300
Cu1—N3^iii	2.112 (2)	C6—C7	1.410 (4)
Cu1—N3	2.112 (2)	C7—C8	1.388 (4)
Cu1—O3^ii	2.2635 (18)	C8—C9	1.398 (3)
Cu1—O3^i	2.2635 (18)	C8—H8	0.9300
F1—C6	1.362 (3)	C10—H10	0.9300
O1—C1	1.269 (3)	C11—C12	1.473 (4)
O1—Cu1^iv	1.9971 (18)	C11—C13	1.481 (4)
O2—C1	1.239 (3)	C11—H11	0.9800
O3—C3	1.247 (3)	C12—C13	1.488 (5)
O3—Cu1^iv	2.2635 (18)	C12—H12A	0.9700
N1—C10	1.341 (3)	C12—H12B	0.9700
N1—C9	1.392 (3)	C13—H13A	0.9700
N1—C11	1.458 (3)	C13—H13B	0.9700
N2—C7	1.391 (3)	C14—C15	1.514 (4)
N2—C14	1.450 (3)	C14—H14A	0.9700
N2—C17	1.473 (3)	C14—H14B	0.9700
N3—C15	1.471 (3)	C15—H15A	0.9700
N3—C16	1.472 (3)	C15—H15B	0.9700
N3—H3N	0.865 (10)	C16—C17	1.523 (4)
C1—C2	1.512 (3)	C16—H16A	0.9700
C2—C10	1.372 (4)	C16—H16B	0.9700
C2—C3	1.439 (4)	C17—H17A	0.9700
C3—C4	1.464 (3)	C17—H17B	0.9700
H1W1—O1W—H1W2	108.3	C7—C8—C9	122.3 (2)
O1^i—Cu1—O1^ii	180.0	C7—C8—H8	118.9
O1^i—Cu1—N3^iii	91.58 (8)	C9—C8—H8	118.9
O1^ii—Cu1—N3^iii	88.42 (8)	N1—C9—C8	121.5 (2)
O1^i—Cu1—N3	88.42 (8)	N1—C9—C4	118.3 (2)
O1^ii—Cu1—N3	91.58 (8)	C8—C9—C4	120.2 (2)
N3^iii—Cu1—N3	180.00 (8)	N1—C10—C2	125.8 (2)
O1^i—Cu1—O3^ii	94.73 (7)	N1—C10—H10	117.1
O1^ii—Cu1—O3^ii	85.27 (7)	C2—C10—H10	117.1
N3^iii—Cu1—O3^ii	94.84 (8)	N1—C11—C12	120.4 (3)
N3—Cu1—O3^ii	85.16 (8)	N1—C11—C13	119.9 (3)
O1^i—Cu1—O3^i	85.27 (7)	C12—C11—C13	60.5 (2)
O1^ii—Cu1—O3^i	94.73 (7)	N1—C11—H11	115.1
N3^iii—Cu1—O3^i	85.16 (8)	C12—C11—H11	115.1
N3—Cu1—O3^i	94.84 (8)	C13—C11—H11	115.1
O3^ii—Cu1—O3^i	180.0	C11—C12—C13	60.0 (2)
C1—O1—Cu1^iv	135.57 (17)	C11—C12—H12A	117.8
C3—O3—Cu1^iv	124.97 (17)	C13—C12—H12A	117.8
C10—N1—C9	119.4 (2)	C11—C12—H12B	117.8
C10—N1—C11	121.1 (2)	C13—C12—H12B	117.8
C9—N1—C11	119.2 (2)	H12A—C12—H12B	114.9
C7—N2—C14	116.6 (2)	C11—C13—C12	59.5 (2)
C7—N2—C17	119.1 (2)	C11—C13—H13A	117.8
C14—N2—C17	109.9 (2)	C12—C13—H13A	117.8
C15—N3—C16	108.4 (2)	C11—C13—H13B	117.8
C15—N3—Cu1	111.39 (17)	C12—C13—H13B	117.8
C16—N3—Cu1	119.09 (17)	H13A—C13—H13B	115.0
C15—N3—H3N	107 (2)	N2—C14—C15	110.2 (2)
C16—N3—H3N	108 (2)	N2—C14—H14A	109.6
Cu1—N3—H3N	102 (2)	C15—C14—H14A	109.6
O2—C1—O1	122.6 (2)	N2—C14—H14B	109.6
O2—C1—C2	117.3 (2)	C15—C14—H14B	109.6
O1—C1—C2	120.0 (2)	H14A—C14—H14B	108.1
C10—C2—C3	118.9 (2)	N3—C15—C14	114.4 (2)
C10—C2—C1	116.0 (2)	N3—C15—H15A	108.7
C3—C2—C1	125.0 (2)	C14—C15—H15A	108.7
O3—C3—C2	125.9 (2)	N3—C15—H15B	108.7
O3—C3—C4	119.3 (2)	C14—C15—H15B	108.7
C2—C3—C4	114.8 (2)	H15A—C15—H15B	107.6
C5—C4—C9	117.6 (2)	N3—C16—C17	113.7 (2)
C5—C4—C3	119.6 (2)	N3—C16—H16A	108.8
C9—C4—C3	122.7 (2)	C17—C16—H16A	108.8
C6—C5—C4	121.1 (2)	N3—C16—H16B	108.8
C6—C5—H5	119.4	C17—C16—H16B	108.8
C4—C5—H5	119.4	H16A—C16—H16B	107.7
C5—C6—F1	118.0 (2)	N2—C17—C16	110.8 (2)
C5—C6—C7	123.1 (2)	N2—C17—H17A	109.5
F1—C6—C7	118.8 (2)	C16—C17—H17A	109.5
C8—C7—N2	123.1 (2)	N2—C17—H17B	109.5
C8—C7—C6	115.7 (2)	C16—C17—H17B	109.5
N2—C7—C6	120.9 (2)	H17A—C17—H17B	108.1
O1^i—Cu1—N3—C15	−56.95 (19)	F1—C6—C7—C8	−174.8 (2)
O1^ii—Cu1—N3—C15	123.05 (19)	C5—C6—C7—N2	176.0 (2)
N3^iii—Cu1—N3—C15	−87 (100)	F1—C6—C7—N2	−0.6 (4)
O3^ii—Cu1—N3—C15	−151.8 (2)	N2—C7—C8—C9	−174.4 (2)
O3^i—Cu1—N3—C15	28.2 (2)	C6—C7—C8—C9	−0.3 (4)
O1^i—Cu1—N3—C16	175.80 (19)	C10—N1—C9—C8	174.6 (2)
O1^ii—Cu1—N3—C16	−4.20 (19)	C11—N1—C9—C8	−0.1 (4)
N3^iii—Cu1—N3—C16	146 (100)	C10—N1—C9—C4	−3.7 (4)
O3^ii—Cu1—N3—C16	80.92 (19)	C11—N1—C9—C4	−178.3 (2)
O3^i—Cu1—N3—C16	−99.08 (19)	C7—C8—C9—N1	179.7 (2)
Cu1^iv—O1—C1—O2	−163.5 (2)	C7—C8—C9—C4	−2.1 (4)
Cu1^iv—O1—C1—C2	19.1 (4)	C5—C4—C9—N1	−178.7 (2)
O2—C1—C2—C10	−15.3 (4)	C3—C4—C9—N1	2.7 (4)
O1—C1—C2—C10	162.3 (2)	C5—C4—C9—C8	3.1 (4)
O2—C1—C2—C3	167.5 (3)	C3—C4—C9—C8	−175.6 (2)
O1—C1—C2—C3	−14.9 (4)	C9—N1—C10—C2	1.9 (4)
Cu1^iv—O3—C3—C2	15.2 (4)	C11—N1—C10—C2	176.5 (3)
Cu1^iv—O3—C3—C4	−162.75 (17)	C3—C2—C10—N1	1.0 (4)
C10—C2—C3—O3	−180.0 (3)	C1—C2—C10—N1	−176.3 (2)
C1—C2—C3—O3	−2.9 (4)	C10—N1—C11—C12	34.2 (4)
C10—C2—C3—C4	−1.9 (3)	C9—N1—C11—C12	−151.2 (3)
C1—C2—C3—C4	175.1 (2)	C10—N1—C11—C13	105.5 (3)
O3—C3—C4—C5	−0.3 (4)	C9—N1—C11—C13	−80.0 (3)
C2—C3—C4—C5	−178.5 (2)	N1—C11—C12—C13	109.4 (3)
O3—C3—C4—C9	178.3 (2)	N1—C11—C13—C12	−110.2 (3)
C2—C3—C4—C9	0.1 (4)	C7—N2—C14—C15	162.9 (2)
C9—C4—C5—C6	−1.7 (4)	C17—N2—C14—C15	−57.7 (3)
C3—C4—C5—C6	177.0 (2)	C16—N3—C15—C14	−52.8 (3)
C4—C5—C6—F1	175.9 (2)	Cu1—N3—C15—C14	174.4 (2)
C4—C5—C6—C7	−0.8 (4)	N2—C14—C15—N3	57.5 (4)
C14—N2—C7—C8	5.3 (4)	C15—N3—C16—C17	51.5 (3)
C17—N2—C7—C8	−130.3 (3)	Cu1—N3—C16—C17	−179.89 (17)
C14—N2—C7—C6	−168.5 (3)	C7—N2—C17—C16	−164.5 (2)
C17—N2—C7—C6	56.0 (4)	C14—N2—C17—C16	57.3 (3)
C5—C6—C7—C8	1.8 (4)	N3—C16—C17—N2	−55.4 (3)

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

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1W1···O2	0.85	1.97	2.812 (5)	175
O1W—H1W2···O1W^v	0.85	2.38	3.225 (15)	176
N3—H3N···O1^vi	0.87 (1)	2.48 (1)	3.331 (3)	167 (3)
N3—H3N···O2^vi	0.87 (1)	2.58 (3)	3.258 (3)	136 (3)

Symmetry codes: (v) −x+2, −y, −z; (vi) −x+2, y+1/2, −z+1/2.