Diaqua-[N-(5-nitro-2-oxidobenzyl-idene)glycinato]copper(II) dihydrate.

In the title complex, [Cu(C(9)H(6)N(2)O(5))(H(2)O)(2)]·2H(2)O, the Cu(II) atom has a square-pyramidal coordination environment with a tridentate N-(5-nitro-2-oxidobenzyl-idene)glycinate Schiff base ligand and a water mol-ecule in the basal plane. The apical site is occupied by an O atom from another coordinated water mol-ecule. The crystal structure is stabilized by O-H⋯O hydrogen bonds, building a two-dimensional network parallel to (100).

Related literature

For general background to metabolic reactions requiring pyridoxal-5′-phosphate as a cofactor, see: Bkouche-Waksman et al. (1988 ▶); Wetmore et al. (2001 ▶); Zabinski & Toney (2001 ▶). For related Schiff base complexes, see: Ganguly et al. (2008 ▶); Jammi et al. (2008 ▶). For a related structure, see: Ueki et al. (1967 ▶).

Experimental

Crystal data

[Cu(C9H6N2O5)(H2O)2]·2H2O

M = 357.76

Monoclinic,

a = 17.306 (4) Å

b = 10.837 (2) Å

c = 7.185 (2) Å

β = 91.63 (1)°

V = 1347.0 (5) Å3

Z = 4

Mo Kα radiation

μ = 1.67 mm−1

T = 293 K

0.25 × 0.20 × 0.15 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.68, T max = 0.78

6554 measured reflections

2369 independent reflections

1107 reflections with I > 2σ(I)

R int = 0.122

Refinement

R[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.074

S = 0.62

2369 reflections

214 parameters

8 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.53 e Å−3

Δρmin = −0.41 e Å−3

Data collection: SMART (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and DIAMOND (Brandenburg, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810010652/hy2290sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810010652/hy2290Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Cu(C9H6N2O5)(H2O)2]·2H2O	F(000) = 732
Mr = 357.76	Dx = 1.764 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1107 reflections
a = 17.306 (4) Å	θ = 2.2–25.0°
b = 10.837 (2) Å	µ = 1.67 mm−1
c = 7.185 (2) Å	T = 293 K
β = 91.63 (1)°	Block, blue
V = 1347.0 (5) Å3	0.25 × 0.2 × 0.15 mm
Z = 4

Bruker SMART 1000 CCD diffractometer	2369 independent reflections
Radiation source: fine-focus sealed tube	1107 reflections with I > 2σ(I)
graphite	Rint = 0.122
φ and ω scans	θmax = 25.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→20
Tmin = 0.68, Tmax = 0.78	k = −8→12
6554 measured reflections	l = −8→8

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.074	H atoms treated by a mixture of independent and constrained refinement
S = 0.62	w = 1/[σ2(Fo2)] where P = (Fo2 + 2Fc2)/3
2369 reflections	(Δ/σ)max < 0.001
214 parameters	Δρmax = 0.53 e Å−3
8 restraints	Δρmin = −0.41 e Å−3

	x	y	z	Uiso*/Ueq
Cu1	0.68418 (3)	0.93382 (5)	1.05603 (9)	0.0332 (2)
N1	0.7825 (2)	0.9810 (4)	0.9699 (6)	0.0313 (11)
N2	0.9642 (3)	0.5241 (5)	0.7898 (7)	0.0533 (15)
C1	0.7707 (3)	0.7116 (5)	1.0012 (7)	0.0262 (13)
C2	0.7740 (3)	0.5812 (4)	0.9948 (7)	0.0342 (14)
H2	0.7324	0.5352	1.0357	0.041*
C3	0.8371 (3)	0.5222 (5)	0.9296 (7)	0.0384 (15)
H3	0.8381	0.4364	0.9284	0.046*
C4	0.8991 (3)	0.5861 (5)	0.8659 (7)	0.0362 (14)
C5	0.8984 (3)	0.7134 (5)	0.8696 (7)	0.0326 (14)
H5	0.9409	0.7572	0.8285	0.039*
C6	0.8343 (2)	0.7767 (4)	0.9347 (7)	0.0241 (12)
C7	0.8375 (2)	0.9109 (4)	0.9286 (6)	0.0319 (14)
H7	0.8832	0.9473	0.8917	0.038*
C8	0.7918 (3)	1.1165 (4)	0.9543 (8)	0.0452 (16)
H8A	0.8051	1.1380	0.8281	0.054*
H8B	0.8334	1.1440	1.0377	0.054*
C9	0.7174 (3)	1.1797 (5)	1.0040 (8)	0.0404 (15)
O1	0.70921 (17)	0.7616 (3)	1.0634 (5)	0.0314 (9)
O2	0.71569 (18)	1.2917 (3)	0.9976 (5)	0.0533 (12)
O3	0.66318 (17)	1.1087 (3)	1.0507 (5)	0.0405 (10)
O4	0.9629 (2)	0.4122 (3)	0.7780 (6)	0.0807 (16)
O5	1.0193 (2)	0.5843 (4)	0.7388 (6)	0.0828 (16)
O6	0.59324 (19)	0.9035 (4)	1.2066 (5)	0.0389 (10)
H6A	0.559 (3)	0.890 (5)	1.134 (5)	0.053*
H6B	0.583 (3)	0.942 (4)	1.297 (5)	0.047*
O7	0.48642 (17)	0.8064 (3)	0.9756 (6)	0.0466 (11)
H7A	0.4407 (11)	0.834 (3)	0.966 (7)	0.053*
H7B	0.481 (2)	0.729 (3)	0.982 (7)	0.053*
O8	0.6090 (2)	0.8942 (3)	0.7687 (6)	0.0403 (10)
H8E	0.5724 (19)	0.857 (3)	0.821 (6)	0.053*
H8D	0.631 (2)	0.844 (4)	0.703 (6)	0.048*
O9	0.58080 (19)	0.0716 (3)	0.4864 (5)	0.0438 (10)
H9D	0.621 (2)	0.105 (4)	0.486 (7)	0.053*
H9B	0.576 (2)	0.026 (4)	0.580 (4)	0.053*

	U11	U22	U33	U12	U13	U23
Cu1	0.0270 (3)	0.0226 (3)	0.0505 (4)	0.0012 (3)	0.0084 (3)	0.0002 (4)
N1	0.028 (2)	0.023 (3)	0.044 (3)	0.006 (2)	0.005 (2)	0.004 (2)
N2	0.039 (3)	0.058 (4)	0.064 (4)	0.024 (3)	0.009 (3)	0.000 (3)
C1	0.022 (3)	0.029 (3)	0.028 (3)	−0.001 (3)	0.003 (3)	0.006 (3)
C2	0.027 (3)	0.027 (3)	0.049 (4)	−0.001 (3)	0.011 (3)	0.007 (3)
C3	0.045 (4)	0.035 (3)	0.036 (4)	0.004 (3)	0.008 (3)	0.003 (3)
C4	0.038 (3)	0.033 (4)	0.038 (4)	0.015 (3)	0.005 (3)	0.000 (3)
C5	0.021 (3)	0.038 (4)	0.039 (4)	−0.004 (3)	0.004 (3)	0.001 (3)
C6	0.023 (3)	0.022 (3)	0.027 (3)	0.001 (2)	0.000 (3)	−0.002 (3)
C7	0.025 (3)	0.029 (3)	0.041 (4)	−0.005 (3)	0.005 (3)	0.001 (3)
C8	0.043 (4)	0.026 (3)	0.067 (5)	−0.003 (3)	0.011 (3)	0.005 (3)
C9	0.038 (4)	0.033 (4)	0.051 (4)	0.000 (3)	0.005 (3)	−0.010 (3)
O1	0.026 (2)	0.020 (2)	0.048 (3)	−0.0014 (15)	0.0092 (19)	0.0026 (17)
O2	0.049 (3)	0.016 (2)	0.096 (3)	−0.0022 (19)	0.011 (2)	−0.005 (2)
O3	0.031 (2)	0.018 (2)	0.073 (3)	−0.0009 (16)	0.010 (2)	−0.0023 (19)
O4	0.077 (3)	0.037 (3)	0.130 (4)	0.025 (2)	0.026 (3)	−0.013 (3)
O5	0.048 (3)	0.068 (3)	0.135 (4)	0.022 (3)	0.047 (3)	−0.003 (3)
O6	0.037 (2)	0.036 (3)	0.044 (3)	0.0001 (19)	0.007 (2)	−0.008 (2)
O7	0.027 (2)	0.035 (2)	0.079 (3)	−0.0045 (19)	0.008 (2)	−0.001 (2)
O8	0.039 (2)	0.029 (2)	0.053 (3)	0.0002 (17)	0.008 (2)	0.000 (2)
O9	0.045 (2)	0.032 (2)	0.056 (3)	−0.004 (2)	0.010 (2)	0.001 (2)

Cu1—N1	1.897 (4)	C5—C6	1.396 (6)
Cu1—O1	1.916 (3)	C5—H5	0.9300
Cu1—O3	1.930 (3)	C6—C7	1.456 (6)
Cu1—O6	1.963 (4)	C7—H7	0.9300
Cu1—O8	2.447 (4)	C8—C9	1.511 (6)
N1—C7	1.260 (5)	C8—H8A	0.9700
N1—C8	1.481 (5)	C8—H8B	0.9700
N2—O4	1.215 (5)	C9—O2	1.215 (5)
N2—O5	1.221 (5)	C9—O3	1.266 (5)
N2—C4	1.433 (6)	O6—H6B	0.80 (3)
C1—O1	1.286 (5)	O6—H6A	0.80 (4)
C1—C6	1.404 (6)	O7—H7A	0.85 (3)
C1—C2	1.415 (6)	O7—H7B	0.85 (3)
C2—C3	1.360 (6)	O8—H8D	0.82 (3)
C2—H2	0.9300	O8—H8E	0.85 (4)
C3—C4	1.367 (6)	O9—H9D	0.78 (3)
C3—H3	0.9300	O9—H9B	0.84 (3)
C4—C5	1.380 (6)
N1—Cu1—O1	93.87 (15)	C5—C4—N2	118.9 (5)
N1—Cu1—O3	84.20 (15)	C4—C5—C6	120.3 (5)
O1—Cu1—O3	177.76 (14)	C4—C5—H5	119.8
N1—Cu1—O6	164.91 (16)	C6—C5—H5	119.8
O1—Cu1—O6	90.32 (15)	C5—C6—C1	120.4 (5)
O3—Cu1—O6	91.26 (15)	C5—C6—C7	116.8 (4)
N1—Cu1—O8	103.44 (14)	C1—C6—C7	122.9 (4)
O1—Cu1—O8	88.09 (13)	N1—C7—C6	124.5 (4)
O3—Cu1—O8	93.45 (13)	N1—C7—H7	117.7
O6—Cu1—O8	91.16 (14)	C6—C7—H7	117.7
C7—N1—C8	119.7 (4)	N1—C8—C9	109.6 (4)
C7—N1—Cu1	127.2 (3)	N1—C8—H8A	109.7
C8—N1—Cu1	113.1 (3)	C9—C8—H8A	109.7
O4—N2—O5	121.6 (5)	N1—C8—H8B	109.7
O4—N2—C4	118.8 (5)	C9—C8—H8B	109.7
O5—N2—C4	119.5 (5)	H8A—C8—H8B	108.2
O1—C1—C6	124.8 (5)	O2—C9—O3	126.9 (5)
O1—C1—C2	117.9 (4)	O2—C9—C8	117.6 (5)
C6—C1—C2	117.3 (5)	O3—C9—C8	115.5 (5)
C3—C2—C1	120.9 (5)	C1—O1—Cu1	126.1 (3)
C3—C2—H2	119.5	C9—O3—Cu1	117.5 (3)
C1—C2—H2	119.5	Cu1—O6—H6B	125 (4)
C2—C3—C4	121.5 (5)	Cu1—O6—H6A	106 (3)
C2—C3—H3	119.2	H6B—O6—H6A	116 (4)
C4—C3—H3	119.2	H7A—O7—H7B	105 (3)
C3—C4—C5	119.5 (5)	H8D—O8—H8E	108 (3)
C3—C4—N2	121.5 (5)	H9D—O9—H9B	112 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6A···O7	0.80 (4)	1.90 (4)	2.666 (5)	162 (5)
O6—H6B···O9i	0.80 (3)	1.96 (3)	2.726 (5)	162 (5)
O7—H7A···O3ii	0.85 (3)	1.90 (3)	2.749 (4)	178 (4)
O7—H7B···O9iii	0.85 (3)	2.03 (4)	2.814 (5)	154 (4)
O8—H8D···O1iv	0.82 (3)	2.05 (3)	2.860 (4)	167 (5)
O8—H8E···O7	0.85 (4)	1.96 (4)	2.792 (5)	166 (4)
O9—H9B···O8v	0.84 (3)	2.04 (2)	2.827 (5)	156 (5)
O9—H9D···O2iv	0.78 (3)	1.99 (3)	2.764 (5)	173 (5)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6A⋯O7	0.80 (4)	1.90 (4)	2.666 (5)	162 (5)
O6—H6B⋯O9i	0.80 (3)	1.96 (3)	2.726 (5)	162 (5)
O7—H7A⋯O3ii	0.85 (3)	1.90 (3)	2.749 (4)	178 (4)
O7—H7B⋯O9iii	0.85 (3)	2.03 (4)	2.814 (5)	154 (4)
O8—H8D⋯O1iv	0.82 (3)	2.05 (3)	2.860 (4)	167 (5)
O8—H8E⋯O7	0.85 (4)	1.96 (4)	2.792 (5)	166 (4)
O9—H9B⋯O8v	0.84 (3)	2.04 (2)	2.827 (5)	156 (5)
O9—H9D⋯O2iv	0.78 (3)	1.99 (3)	2.764 (5)	173 (5)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) .