Tetra­aqua(5-fluoro­uracil-1-acetato-O)copper(II) tetra­hydrate

In the title complex, [Cu(C₆H₄FN₂O₄)₂(H₂O)₄]·4H₂O, the Cu atom is located in the centre of a distorted octahedral geometry. The coordination atoms are six O atoms provided by two carboxyl­ate groups [coordinated in a monodentate mode, with Cu-O = 1.9551 (10) Å] and four water mol­ecules [Cu-O = 1.9241 (13) and 2.5771 (14) Å]. In addition, one intramolecular hydrogen bond and ten intermolecular hydrogen bonds make up a three-dimensional network.

Computing details

Data collection: CAD-4-PC (Enraf-Nonius, 1989); cell refinement: CAD-4-PC; data reduction: TEXSAN (Molecular Structure Corporation, 1989); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); software used to prepare material for publication: SHELXL97.

Tetraaqua(5-fluoro-uracil-1-acetato-O)-copper (II) tetrahydrate

Crystal data

[Cu(C6H4FN2O4)2(H2O)4]·4H2O	F(000) = 598
Mr = 581.89	Dx = 1.745 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 8.304 (1) Å	Cell parameters from 150 reflections
b = 12.044 (2) Å	θ = 16.1–16.9°
c = 11.082 (2) Å	µ = 1.09 mm^−1
β = 92.47 (1)°	T = 293 K
V = 1107.3 (3) Å^3	Prismatic, blue
Z = 2	0.30 × 0.15 × 0.10 mm

Data collection

Enraf-nonius CAD-4 diffractometer	1838 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.0
Graphite monochromator	θmax = 25.0°, θmin = 2.5°
ω/2θ scans	h = −9→9
Absorption correction: ψ scan (TEXSAN; Molecular Structure Corporation, 1989)	k = 0→14
Tmin = 0.851, Tmax = 0.897	l = 0→13
1941 measured reflections	3 standard reflections every 400 reflections
1941 independent reflections	intensity decay: none

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)] = 0.020	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.056	H-atom parameters constrained
S = 1.03	w = 1/[σ^2(Fo^2) + (0.020P)^2 + 0.444P] where P = (Fo^2 + 2Fc^2)/3
1941 reflections	(Δ/σ)max < 0.001
160 parameters	Δρmax = 0.29 e Å^−3
34 restraints	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
Cu	0.5000	0.0000	0.0000	0.02271 (10)
O1	0.38908 (15)	0.10354 (12)	0.18221 (11)	0.0403 (3)
H1A	0.310 (2)	0.122 (2)	0.158 (2)	0.060*
H1B	0.380 (3)	0.083 (2)	0.2383 (15)	0.060*
O2	0.39173 (16)	−0.13307 (11)	0.04805 (12)	0.0411 (3)
H2A	0.395 (3)	−0.1775 (17)	0.007 (2)	0.062*
H2B	0.3063 (19)	−0.122 (2)	0.051 (2)	0.062*
O3	0.67913 (12)	−0.03487 (9)	0.11398 (9)	0.0267 (2)
O4	0.85492 (13)	−0.10260 (10)	−0.01351 (9)	0.0349 (3)
O5	0.97799 (14)	0.11773 (9)	0.29680 (10)	0.0339 (3)
O6	0.67100 (17)	0.03682 (10)	0.61472 (11)	0.0439 (3)
N1	0.87716 (14)	−0.05803 (10)	0.30885 (10)	0.0230 (3)
N2	0.82678 (15)	0.07368 (10)	0.45618 (11)	0.0264 (3)
H2	0.8433	0.1392	0.4850	0.032*
F	0.62339 (16)	−0.17610 (10)	0.52978 (12)	0.0625 (4)
C1	0.81274 (16)	−0.07439 (11)	0.08810 (12)	0.0207 (3)
C2	0.93783 (17)	−0.08952 (13)	0.19217 (12)	0.0250 (3)
H2C	0.9712	−0.1667	0.1954	0.030*
H2D	1.0320	−0.0449	0.1766	0.030*
C3	0.89914 (17)	0.04936 (12)	0.34906 (12)	0.0227 (3)
C4	0.7316 (2)	0.00494 (12)	0.52158 (14)	0.0291 (3)
C5	0.7137 (2)	−0.10399 (13)	0.47033 (16)	0.0339 (4)
C6	0.78282 (19)	−0.13151 (13)	0.36918 (14)	0.0301 (3)
H6	0.7671	−0.2026	0.3380	0.036*
O7	0.87955 (14)	0.21563 (10)	0.06382 (10)	0.0304 (2)
H7A	0.867 (2)	0.2082 (18)	0.1282 (13)	0.046*
H7B	0.950 (2)	0.1856 (17)	0.0536 (19)	0.046*
O8	0.37913 (18)	−0.23677 (12)	0.25723 (12)	0.0450 (3)
H8A	0.343 (3)	−0.1991 (19)	0.298 (2)	0.068*
H8B	0.458 (2)	−0.249 (2)	0.287 (2)	0.068*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu	0.01960 (14)	0.02279 (15)	0.02554 (15)	0.00225 (9)	−0.00148 (10)	0.00515 (9)
O1	0.0378 (7)	0.0507 (8)	0.0322 (6)	−0.0040 (6)	0.0007 (5)	0.0129 (6)
O2	0.0419 (7)	0.0391 (7)	0.0413 (7)	−0.0105 (6)	−0.0092 (6)	0.0115 (5)
O3	0.0231 (5)	0.0343 (6)	0.0227 (5)	0.0086 (4)	0.0007 (4)	0.0001 (4)
O4	0.0342 (6)	0.0483 (7)	0.0221 (5)	0.0099 (5)	−0.0003 (4)	−0.0069 (5)
O5	0.0437 (6)	0.0303 (6)	0.0286 (5)	−0.0078 (5)	0.0111 (5)	0.0054 (5)
O6	0.0649 (8)	0.0339 (6)	0.0352 (7)	0.0055 (6)	0.0273 (6)	0.0032 (5)
N1	0.0259 (6)	0.0227 (6)	0.0202 (6)	0.0036 (5)	−0.0006 (5)	0.0002 (5)
N2	0.0384 (7)	0.0188 (6)	0.0226 (6)	−0.0014 (5)	0.0062 (5)	−0.0008 (5)
F	0.0824 (9)	0.0397 (6)	0.0686 (8)	−0.0246 (6)	0.0396 (7)	0.0015 (6)
C1	0.0256 (7)	0.0158 (6)	0.0207 (7)	−0.0007 (5)	0.0016 (5)	0.0009 (5)
C2	0.0251 (7)	0.0275 (8)	0.0227 (7)	0.0069 (6)	0.0024 (6)	−0.0036 (6)
C3	0.0261 (7)	0.0220 (7)	0.0197 (6)	0.0023 (6)	−0.0016 (5)	0.0018 (5)
C4	0.0333 (8)	0.0273 (8)	0.0270 (8)	0.0008 (6)	0.0047 (6)	0.0062 (6)
C5	0.0383 (9)	0.0233 (8)	0.0411 (9)	−0.0084 (6)	0.0128 (7)	0.0051 (7)
C6	0.0359 (8)	0.0208 (7)	0.0337 (8)	−0.0038 (6)	0.0016 (6)	−0.0008 (6)
O7	0.0341 (6)	0.0312 (6)	0.0262 (5)	0.0029 (5)	0.0058 (5)	0.0059 (5)
O8	0.0581 (8)	0.0416 (8)	0.0358 (7)	0.0087 (6)	0.0069 (6)	0.0045 (6)

Geometric parameters (Å, º)

Cu—O2	1.9241 (13)	N1—C2	1.4580 (18)
Cu—O2^i	1.9241 (13)	N2—C4	1.373 (2)
Cu—O3^i	1.9551 (10)	N2—C3	1.3847 (19)
Cu—O3	1.9551 (10)	N2—H2	0.8600
Cu—O1	2.5771 (14)	F—C5	1.3391 (18)
O1—H1A	0.734 (14)	C1—C2	1.5295 (19)
O1—H1B	0.675 (14)	C2—H2C	0.9700
O2—H2A	0.705 (14)	C2—H2D	0.9700
O2—H2B	0.725 (14)	C4—C5	1.435 (2)
O3—C1	1.2519 (17)	C5—C6	1.323 (2)
O4—C1	1.2409 (17)	C6—H6	0.9300
O5—C3	1.2144 (18)	O7—H7A	0.732 (14)
O6—C4	1.229 (2)	O7—H7B	0.698 (14)
N1—C6	1.374 (2)	O8—H8A	0.718 (14)
N1—C3	1.378 (2)	O8—H8B	0.738 (14)
O2—Cu—O2^i	180.00 (4)	O4—C1—O3	126.84 (13)
O2—Cu—O3^i	90.35 (5)	O4—C1—C2	116.26 (12)
O2^i—Cu—O3^i	89.65 (5)	O3—C1—C2	116.90 (12)
O2—Cu—O3	89.65 (5)	N1—C2—C1	112.85 (11)
O2^i—Cu—O3	90.35 (5)	N1—C2—H2C	109.0
O3^i—Cu—O3	180.00 (8)	C1—C2—H2C	109.0
O2—Cu—O1	89.95 (5)	N1—C2—H2D	109.0
O2^i—Cu—O1	90.05 (5)	C1—C2—H2D	109.0
O3^i—Cu—O1	96.58 (4)	H2C—C2—H2D	107.8
O3—Cu—O1	83.42 (4)	O5—C3—N1	123.29 (13)
Cu—O1—H1A	101.8 (19)	O5—C3—N2	121.89 (13)
Cu—O1—H1B	127 (2)	N1—C3—N2	114.81 (12)
H1A—O1—H1B	109 (2)	O6—C4—N2	121.38 (14)
Cu—O2—H2A	115 (2)	O6—C4—C5	125.38 (15)
Cu—O2—H2B	109 (2)	N2—C4—C5	113.23 (14)
H2A—O2—H2B	104 (2)	C6—C5—F	121.79 (15)
C1—O3—Cu	126.21 (9)	C6—C5—C4	121.54 (14)
C6—N1—C3	121.16 (12)	F—C5—C4	116.67 (14)
C6—N1—C2	119.33 (12)	C5—C6—N1	121.87 (14)
C3—N1—C2	119.02 (12)	C5—C6—H6	119.1
C4—N2—C3	127.30 (13)	N1—C6—H6	119.1
C4—N2—H2	116.3	H7A—O7—H7B	104 (2)
C3—N2—H2	116.3	H8A—O8—H8B	103 (2)
O2—Cu—O3—C1	102.87 (13)	C2—N1—C3—N2	175.26 (11)
O2^i—Cu—O3—C1	−77.13 (13)	C4—N2—C3—O5	178.02 (15)
O3^i—Cu—O3—C1	−116.00 (10)	C4—N2—C3—N1	−3.3 (2)
O1—Cu—O3—C1	−167.14 (12)	C3—N2—C4—O6	−178.49 (15)
Cu—O3—C1—O4	−2.8 (2)	C3—N2—C4—C5	2.0 (2)
Cu—O3—C1—C2	177.08 (9)	O6—C4—C5—C6	179.79 (17)
C6—N1—C2—C1	80.72 (16)	N2—C4—C5—C6	−0.7 (2)
C3—N1—C2—C1	−91.41 (15)	O6—C4—C5—F	−0.1 (3)
O4—C1—C2—N1	−178.05 (13)	N2—C4—C5—F	179.47 (15)
O3—C1—C2—N1	2.05 (18)	F—C5—C6—N1	−179.18 (15)
C6—N1—C3—O5	−178.02 (14)	C4—C5—C6—N1	1.0 (3)
C2—N1—C3—O5	−6.0 (2)	C3—N1—C6—C5	−2.4 (2)
C6—N1—C3—N2	3.28 (19)	C2—N1—C6—C5	−174.35 (15)

Symmetry code: (i) −x+1, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O7—H7A···O5	0.73 (1)	2.32 (2)	2.9228 (16)	141 (2)
O1—H1A···O4^i	0.73 (1)	2.08 (2)	2.6971 (17)	143 (3)
O1—H1B···O6^ii	0.68 (1)	2.23 (2)	2.8753 (17)	160 (3)
O2—H2A···F^iii	0.71 (1)	2.59 (2)	3.0096 (19)	120 (2)
O2—H2B···O7^i	0.73 (1)	2.26 (2)	2.7128 (17)	121 (2)
N2—H2···O7^iv	0.86	1.97	2.8300 (17)	176
O7—H7A···O8^v	0.73 (1)	2.54 (2)	3.0402 (18)	127 (2)
O7—H7B···O4^vi	0.70 (1)	1.97 (1)	2.6706 (16)	176 (2)
O8—H8A···O6^ii	0.72 (1)	2.18 (2)	2.8350 (19)	151 (3)
O8—H8A···O7^vii	0.72 (1)	2.65 (2)	3.0402 (18)	116 (2)
O8—H8B···O1^vii	0.74 (1)	2.20 (2)	2.783 (2)	137 (3)

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