trans-Di­aqua­bis(N-acetyl­anthranilato-O,O')copper(II)

The title monomeric copper(II) complex, [Cu(C₉H₈NO₃)₂(H₂O)₂], (I), shows a square-planar coordination and has an inversion centre at the Cu atom. The carboxyl­ate group of the N-acetyl­anthranilate ion acts as a monodentate donor ligand to copper and as an acceptor of an intramolecular O-H...O hydrogen bond from the coordinated water mol­ecule, with an O...O distance of 2.581 (2) Å.

S1. Experimental

N-Acetylanthranilic acid (358 mg, 2.0 mmol) and CuCO₃·Cu(OH)₂·H₂O (120 mg, 0.5 mmol) were suspended in an aqueous ethanol (1:1, 60 ml) and stirred for 3 h at 348 K. After filtration, the solution was evaporated to dryness. The green residue was dissolved in ethanol (10 ml), from which light-green crystals of (I) were grown.

S2. Refinement

The water H atoms were located in difference syntheses and the positions of the other H atoms were calculated geometrically and constrained (the C—H, N—H and O—H distances are 0.96 Å and U_iso(H) = 0.1 Ų).

Computing details

Data collection: AFC/MSC Diffractometer Control System (Rigaku Corporation, 1993); cell refinement: AFC/MSC Diffractometer Control System (Rigaku Corporation, 1993); data reduction: local programs; program(s) used to solve structure: CRYSTAN-GM (Edwards et al., 1996); program(s) used to refine structure: CRYSTAN-GM; software used to prepare material for publication: CRYSTAN-GM.

trans-diaqua-bis(N-acetylanthranilato-O,O')copper(II)

Crystal data

[Cu(C9H8NO3)2(H2O)2]	F(000) = 470
Mr = 455.91	Dx = 1.663 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 5.245 (2) Å	Cell parameters from 25 reflections
b = 16.915 (2) Å	θ = 14.6–14.9°
c = 10.461 (2) Å	µ = 1.25 mm^−1
β = 101.21 (2)°	T = 296 K
V = 910.4 (4) Å^3	Prism, light green
Z = 2	0.6 × 0.4 × 0.4 mm

Data collection

Rigaku AFC-5 diffractometer	Rint = 0.02
θ–2θ scans	θmax = 30°
Absorption correction: integration (Coppens et al., 1965)	h = 0→7
Tmin = 0.479, Tmax = 0.703	k = 0→23
2918 measured reflections	l = −14→14
2660 independent reflections	3 standard reflections every 100 reflections
2176 reflections with |Fo| > 3σ(|Fo|)	intensity decay: none

Refinement

Refinement on F	H-atom parameters constrained
R[F^2 > 2σ(F^2)] = 0.052	w = 1/[σ^2(F) + 0.000225F^2]
wR(F^2) = 0.058	(Δ/σ)max = 0.008
S = 1.40	Δρmax = 1.13 e Å^−3
2176 reflections	Δρmin = −1.06 e Å^−3
133 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0	0	0	0.0237 (1)
O2	−0.2580 (3)	−0.41578 (8)	0.3185 (2)	0.0427 (5)
O3	−0.1777 (3)	−0.06314 (7)	0.1147 (1)	0.0283 (4)
O4	0.0382 (3)	−0.17706 (7)	0.1255 (1)	0.0326 (4)
O5	−0.2801 (2)	0.07672 (7)	−0.0063 (1)	0.0287 (4)
N6	−0.1553 (3)	−0.29721 (9)	0.2368 (2)	0.0326 (5)
C7	0.0335 (5)	−0.4144 (1)	0.1691 (3)	0.0484 (8)
C8	−0.1418 (4)	−0.3768 (1)	0.2497 (2)	0.0310 (6)
C9	−0.2970 (4)	−0.2414 (1)	0.2931 (2)	0.0265 (5)
C10	−0.4534 (4)	−0.2626 (1)	0.3812 (2)	0.0343 (6)
C11	−0.5853 (4)	−0.2056 (1)	0.4365 (2)	0.0403 (7)
C12	−0.5689 (4)	−0.1270 (1)	0.4047 (2)	0.0406 (7)
C13	−0.4208 (4)	−0.1053 (1)	0.3142 (2)	0.0316 (6)
C14	−0.2837 (3)	−0.1611 (1)	0.2573 (2)	0.0238 (5)
C15	−0.1263 (3)	−0.1333 (1)	0.1596 (2)	0.0238 (5)
H5A	−0.46287	0.06572	−0.02839	0.10*
H5B	−0.21157	0.11812	−0.05249	0.10*
H6	−0.05155	−0.27541	0.17931	0.10*
H7A	0.12491	−0.38401	0.11486	0.10*
H7B	−0.07259	−0.45131	0.11256	0.10*
H7C	0.16331	−0.44301	0.22876	0.10*
H10	−0.46885	−0.31733	0.40339	0.10*
H11	−0.68945	−0.22103	0.49820	0.10*
H12	−0.65860	−0.08775	0.44534	0.10*
H13	−0.41351	−0.05081	0.28957	0.10*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0232 (2)	0.0202 (1)	0.0283 (2)	0.0037 (1)	0.0123 (1)	0.0066 (2)
O2	0.0487 (9)	0.0300 (8)	0.0508 (10)	−0.0002 (7)	0.0196 (8)	0.0129 (7)
O3	0.0304 (7)	0.0229 (6)	0.0315 (8)	0.0018 (5)	0.0137 (6)	0.0061 (5)
O4	0.0320 (7)	0.0267 (7)	0.0404 (8)	0.0043 (6)	0.0174 (6)	0.0098 (6)
O5	0.0252 (6)	0.0250 (6)	0.0366 (8)	0.0043 (5)	0.0126 (6)	0.0075 (6)
N6	0.0372 (9)	0.0273 (8)	0.0342 (9)	0.0023 (7)	0.0159 (8)	0.0095 (7)
C7	0.059 (1)	0.037 (1)	0.048 (1)	0.011 (1)	0.022 (1)	0.007 (1)
C8	0.033 (1)	0.028 (1)	0.032 (1)	0.001 (1)	0.003 (1)	0.006 (1)
C9	0.0273 (9)	0.0284 (9)	0.0239 (9)	−0.0009 (7)	0.0045 (7)	0.0051 (7)
C10	0.037 (1)	0.035 (1)	0.033 (1)	−0.002 (1)	0.013 (1)	0.011 (1)
C11	0.043 (1)	0.048 (1)	0.031 (1)	0.000 (1)	0.018 (1)	0.011 (1)
C12	0.044 (1)	0.041 (1)	0.033 (1)	0.001 (1)	0.018 (1)	0.000 (1)
C13	0.034 (1)	0.030 (1)	0.028 (1)	−0.002 (1)	0.009 (1)	0.001 (1)
C14	0.0240 (8)	0.0258 (9)	0.0211 (9)	−0.0033 (7)	0.0043 (7)	0.0033 (7)
C15	0.0233 (8)	0.0246 (8)	0.0221 (9)	−0.0047 (7)	0.0036 (7)	0.0012 (7)

Geometric parameters (Å, º)

Cu1—O3	1.970 (2)	C12—C13	1.386 (3)
Cu1—O3^i	1.970 (2)	C13—C14	1.389 (3)
Cu1—O5	1.952 (2)	C14—C15	1.508 (3)
Cu1—O5^i	1.952 (2)	O5—H5A	0.960
O2—C8	1.223 (3)	O5—H5B	0.959
O3—C15	1.285 (3)	N6—H6	0.960
O4—C15	1.241 (3)	C7—H7A	0.960
N6—C8	1.354 (3)	C7—H7B	0.960
N6—C9	1.400 (3)	C7—H7C	0.960
C7—C8	1.504 (4)	C10—H10	0.961
C9—C10	1.394 (3)	C11—H11	0.959
C9—C14	1.415 (3)	C12—H12	0.960
C10—C11	1.378 (3)	C13—H13	0.960
C11—C12	1.377 (4)
O3—Cu1—O3^i	180.0	O3—C15—C14	115.6 (2)
O3—Cu1—O5	86.5 (1)	O4—C15—C14	120.7 (2)
O3—Cu1—O5^i	93.5 (1)	Cu1—O5—H5A	126.1
O3^i—Cu1—O5	93.5 (1)	Cu1—O5—H5B	98.6
O3^i—Cu1—O5^i	86.5 (1)	Cu1^i—O5—H5A	126.1
O5—Cu1—O5^i	180.0	Cu1^i—O5—H5B	98.6
Cu1—O3—C15	129.2 (2)	H5A—O5—H5B	118.3
Cu1^i—O3—C15	129.2 (2)	C8—N6—H6	114.8
C8—N6—C9	130.6 (2)	C9—N6—H6	114.6
O2—C8—N6	124.9 (2)	C8—C7—H7A	122.3
O2—C8—C7	122.1 (2)	C8—C7—H7B	106.0
N6—C8—C7	113.0 (2)	C8—C7—H7C	106.4
N6—C9—C10	122.2 (2)	H7A—C7—H7B	106.3
N6—C9—C14	118.6 (2)	H7A—C7—H7C	106.4
C10—C9—C14	119.2 (2)	H7B—C7—H7C	109.0
C9—C10—C11	120.4 (2)	C9—C10—H10	119.7
C10—C11—C12	120.9 (3)	C11—C10—H10	119.9
C11—C12—C13	119.4 (2)	C10—C11—H11	119.4
C12—C13—C14	121.2 (2)	C12—C11—H11	119.7
C9—C14—C13	118.8 (2)	C11—C12—H12	120.2
C9—C14—C15	122.8 (2)	C13—C12—H12	120.4
C13—C14—C15	118.4 (2)	C12—C13—H13	119.7
O3—C15—O4	123.6 (2)	C14—C13—H13	119.1

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5B···O4^i	0.96	1.64	2.581 (2)	167
N6—H6···O4	0.96	1.85	2.641 (2)	138

Symmetry code: (i) −x, −y, −z.