{2-[(2-Acetyl-hydrazin-1-yl-idene)methyl-κN,O]-6-methoxy-phenolato-κO}(nitrato-κO)copper(II) monohydrate.

In the title complex, [Cu(C(10)H(11)N(2)O(3))(NO(3))]·H(2)O, prepared from the Schiff base N'-(3-meth-oxy-2-oxidobenzyl-idene)-acetohydrazide, the Cu(II) atom is coordinated by two O atoms and one N atom from the ligand and one O atom from a nitrate group in a distorted square-planar geometry. The Cu(II) atom has a weak inter-action with another O atom of the nitrate group. The two O atoms of the tridentate Schiff base ligand are in a trans arrangement. O-H⋯O and N-H⋯O hydrogen bonds involving the uncoordinated water mol-ecule are observed.

Related literature

For related structures, see: Ainscough et al. (1998 ▶); Koh et al. (1998 ▶); Tamboura et al. (2009 ▶); You & Zhu (2004 ▶).

Experimental

Crystal data

[Cu(C10H11N2O3)(NO3)]·H2O

M = 350.77

Monoclinic,

a = 9.274 (2) Å

b = 10.455 (4) Å

c = 13.726 (4) Å

β = 95.16 (5)°

V = 1325.5 (7) Å3

Z = 4

Mo Kα radiation

μ = 1.69 mm−1

T = 293 K

0.40 × 0.28 × 0.20 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997 ▶) T min = 0.56, T max = 0.72

5500 measured reflections

3046 independent reflections

2493 reflections with I > 2σ(I)

R int = 0.021

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.090

S = 1.05

3046 reflections

192 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.44 e Å−3

Data collection: COLLECT (Nonius, 1998 ▶); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810000632/hy2267sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810000632/hy2267Isup2.hkl

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

[Cu(C10H11N2O3)(NO3)]·H2O	F(000) = 716
Mr = 350.77	Dx = 1.758 Mg m−3
Monoclinic, P21/c	Melting point: 469 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71070 Å
a = 9.274 (2) Å	Cell parameters from 12725 reflections
b = 10.455 (4) Å	θ = 1.0–27.5°
c = 13.726 (4) Å	µ = 1.69 mm−1
β = 95.16 (5)°	T = 293 K
V = 1325.5 (7) Å3	Prism, green
Z = 4	0.40 × 0.28 × 0.20 mm

Nonius KappaCCD diffractometer	3046 independent reflections
Radiation source: fine-focus sealed tube	2493 reflections with I > 2σ(I)
graphite	Rint = 0.021
φ and ω scans	θmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	h = −12→12
Tmin = 0.56, Tmax = 0.72	k = −13→12
5500 measured reflections	l = −17→17

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0515P)2 + 0.2512P] where P = (Fo2 + 2Fc2)/3
3046 reflections	(Δ/σ)max = 0.001
192 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.44 e Å−3

	x	y	z	Uiso*/Ueq
Cu1	0.09934 (3)	0.23847 (2)	0.104081 (19)	0.03448 (11)
O1	0.20916 (16)	0.08774 (13)	0.10007 (12)	0.0391 (3)
O2	0.39441 (16)	−0.09065 (15)	0.07532 (13)	0.0489 (4)
O3	−0.02563 (16)	0.38826 (14)	0.12039 (12)	0.0417 (4)
O4	0.25659 (17)	0.34556 (16)	0.06197 (12)	0.0464 (4)
O5	0.40681 (19)	0.48337 (19)	0.13003 (19)	0.0784 (7)
O6	0.2791 (2)	0.3648 (2)	0.21931 (14)	0.0662 (5)
O7	−0.45344 (19)	0.13264 (18)	0.18452 (13)	0.0589 (5)
H1O	−0.5371	0.1148	0.1455	0.071*
H2O	−0.4318	0.0772	0.2358	0.071*
N1	−0.07247 (18)	0.14998 (17)	0.13266 (12)	0.0321 (4)
N2	−0.1848 (2)	0.23436 (17)	0.14647 (14)	0.0362 (4)
H2N	−0.2694	0.2092	0.1591	0.043*
N3	0.31622 (19)	0.39954 (18)	0.13960 (18)	0.0477 (5)
C1	0.1588 (2)	−0.02931 (19)	0.10347 (14)	0.0323 (4)
C2	0.0145 (2)	−0.0638 (2)	0.11923 (14)	0.0336 (4)
C3	−0.0258 (3)	−0.1947 (2)	0.11989 (16)	0.0404 (5)
H3	−0.1210	−0.2163	0.1288	0.048*
C4	0.0720 (3)	−0.2894 (2)	0.10779 (16)	0.0435 (5)
H4	0.0438	−0.3747	0.1087	0.052*
C5	0.2160 (3)	−0.2570 (2)	0.09391 (17)	0.0405 (5)
H5	0.2833	−0.3214	0.0865	0.049*
C6	0.2581 (2)	−0.1313 (2)	0.09123 (15)	0.0351 (4)
C7	−0.0955 (2)	0.0287 (2)	0.13384 (15)	0.0360 (5)
H7	−0.1876	−0.0002	0.1447	0.043*
C8	0.5026 (3)	−0.1853 (3)	0.0650 (2)	0.0549 (6)
H8A	0.5203	−0.2318	0.1251	0.082*
H8B	0.5904	−0.1446	0.0494	0.082*
H8C	0.4699	−0.2432	0.0134	0.082*
C9	−0.1505 (2)	0.3575 (2)	0.13847 (15)	0.0371 (5)
C10	−0.2645 (3)	0.4550 (2)	0.14953 (19)	0.0504 (6)
H10A	−0.2274	0.5200	0.1944	0.076*
H10B	−0.3470	0.4149	0.1742	0.076*
H10C	−0.2929	0.4931	0.0871	0.076*

	U11	U22	U33	U12	U13	U23
Cu1	0.03077 (17)	0.02852 (15)	0.04481 (18)	−0.00120 (9)	0.00701 (11)	−0.00130 (10)
O1	0.0317 (8)	0.0291 (7)	0.0572 (9)	−0.0018 (6)	0.0082 (7)	−0.0017 (6)
O2	0.0358 (9)	0.0386 (9)	0.0730 (11)	0.0047 (7)	0.0088 (8)	−0.0013 (8)
O3	0.0378 (8)	0.0344 (8)	0.0534 (9)	0.0008 (6)	0.0068 (7)	−0.0025 (7)
O4	0.0435 (9)	0.0413 (9)	0.0556 (10)	−0.0083 (7)	0.0114 (7)	−0.0026 (7)
O5	0.0368 (10)	0.0432 (11)	0.154 (2)	−0.0105 (8)	0.0007 (12)	−0.0053 (12)
O6	0.0606 (12)	0.0783 (14)	0.0591 (12)	0.0034 (10)	0.0021 (10)	−0.0132 (10)
O7	0.0467 (10)	0.0621 (12)	0.0672 (12)	−0.0145 (8)	0.0010 (9)	0.0066 (9)
N1	0.0288 (8)	0.0329 (9)	0.0349 (9)	0.0014 (7)	0.0042 (7)	−0.0006 (7)
N2	0.0283 (9)	0.0406 (10)	0.0404 (10)	0.0032 (7)	0.0065 (8)	−0.0008 (7)
N3	0.0280 (9)	0.0326 (10)	0.0819 (16)	0.0059 (8)	0.0016 (10)	−0.0071 (10)
C1	0.0359 (11)	0.0303 (10)	0.0300 (10)	−0.0017 (8)	−0.0009 (8)	0.0011 (8)
C2	0.0366 (11)	0.0336 (10)	0.0304 (10)	−0.0023 (8)	0.0030 (8)	0.0009 (8)
C3	0.0422 (13)	0.0352 (12)	0.0439 (12)	−0.0087 (9)	0.0051 (10)	0.0011 (10)
C4	0.0575 (15)	0.0283 (10)	0.0442 (12)	−0.0059 (10)	0.0011 (11)	0.0021 (9)
C5	0.0499 (14)	0.0320 (11)	0.0386 (12)	0.0059 (9)	−0.0008 (10)	0.0000 (8)
C6	0.0358 (11)	0.0354 (11)	0.0335 (10)	0.0018 (9)	0.0011 (8)	−0.0005 (8)
C7	0.0315 (11)	0.0403 (12)	0.0364 (11)	−0.0064 (8)	0.0033 (9)	0.0012 (9)
C8	0.0411 (13)	0.0506 (15)	0.0730 (17)	0.0135 (11)	0.0048 (12)	−0.0068 (13)
C9	0.0374 (12)	0.0396 (11)	0.0337 (11)	0.0045 (9)	−0.0007 (8)	−0.0009 (9)
C10	0.0473 (14)	0.0481 (14)	0.0555 (14)	0.0140 (11)	0.0023 (11)	0.0005 (11)

Cu1—N1	1.9134 (18)	C1—C2	1.422 (3)
Cu1—O1	1.8798 (15)	C1—C6	1.428 (3)
Cu1—O3	1.9730 (16)	C2—C3	1.419 (3)
Cu1—O4	1.9663 (16)	C2—C7	1.433 (3)
Cu1—O6	2.559 (2)	C3—C4	1.363 (4)
O1—C1	1.312 (2)	C3—H3	0.9300
O2—C6	1.370 (3)	C4—C5	1.407 (3)
O2—C8	1.425 (3)	C4—H4	0.9300
O3—C9	1.248 (3)	C5—C6	1.373 (3)
O4—N3	1.286 (3)	C5—H5	0.9300
O5—N3	1.229 (3)	C7—H7	0.9300
O6—N3	1.231 (3)	C8—H8A	0.9600
O7—H1O	0.92	C8—H8B	0.9600
O7—H2O	0.92	C8—H8C	0.9600
N1—C7	1.286 (3)	C9—C10	1.486 (3)
N1—N2	1.391 (2)	C10—H10A	0.9600
N2—C9	1.333 (3)	C10—H10B	0.9600
N2—H2N	0.8600	C10—H10C	0.9600
O1—Cu1—N1	93.67 (7)	C4—C3—C2	121.4 (2)
O1—Cu1—O4	92.90 (7)	C4—C3—H3	119.3
N1—Cu1—O4	171.47 (7)	C2—C3—H3	119.3
O1—Cu1—O3	173.76 (6)	C3—C4—C5	119.5 (2)
N1—Cu1—O3	81.49 (7)	C3—C4—H4	120.3
O4—Cu1—O3	92.30 (7)	C5—C4—H4	120.3
O1—Cu1—O6	97.25 (7)	C6—C5—C4	120.7 (2)
O3—Cu1—O6	82.93 (7)	C6—C5—H5	119.7
O4—Cu1—O6	55.16 (7)	C4—C5—H5	119.7
N1—Cu1—O6	129.12 (7)	O2—C6—C5	124.8 (2)
C1—O1—Cu1	125.84 (13)	O2—C6—C1	113.64 (18)
C6—O2—C8	117.93 (18)	C5—C6—C1	121.6 (2)
C9—O3—Cu1	112.53 (14)	N1—C7—C2	122.85 (19)
N3—O4—Cu1	106.34 (13)	N1—C7—H7	118.6
H1O—O7—H2O	115.6	C2—C7—H7	118.6
C7—N1—N2	119.75 (18)	O2—C8—H8A	109.5
C7—N1—Cu1	128.43 (15)	O2—C8—H8B	109.5
N2—N1—Cu1	111.66 (13)	H8A—C8—H8B	109.5
C9—N2—N1	114.45 (17)	O2—C8—H8C	109.5
C9—N2—H2N	122.8	H8A—C8—H8C	109.5
N1—N2—H2N	122.8	H8B—C8—H8C	109.5
O5—N3—O6	123.6 (2)	O3—C9—N2	119.85 (19)
O5—N3—O4	118.1 (2)	O3—C9—C10	121.7 (2)
O6—N3—O4	118.24 (19)	N2—C9—C10	118.4 (2)
O1—C1—C2	125.80 (19)	C9—C10—H10A	109.5
O1—C1—C6	117.19 (18)	C9—C10—H10B	109.5
C2—C1—C6	117.01 (18)	H10A—C10—H10B	109.5
C3—C2—C1	119.86 (19)	C9—C10—H10C	109.5
C3—C2—C7	117.3 (2)	H10A—C10—H10C	109.5
C1—C2—C7	122.82 (19)	H10B—C10—H10C	109.5
N1—Cu1—O1—C1	7.99 (17)	C1—C2—C3—C4	1.5 (3)
O4—Cu1—O1—C1	−166.57 (17)	C7—C2—C3—C4	−179.2 (2)
N1—Cu1—O3—C9	−1.29 (15)	C2—C3—C4—C5	−0.3 (3)
O4—Cu1—O3—C9	172.83 (15)	C3—C4—C5—C6	−0.8 (4)
O1—Cu1—O4—N3	−101.08 (13)	C8—O2—C6—C5	−2.9 (3)
O3—Cu1—O4—N3	75.48 (14)	C8—O2—C6—C1	178.26 (19)
O1—Cu1—N1—C7	−7.63 (19)	C4—C5—C6—O2	−178.0 (2)
O3—Cu1—N1—C7	176.33 (18)	C4—C5—C6—C1	0.7 (3)
O1—Cu1—N1—N2	177.15 (13)	O1—C1—C6—O2	−1.3 (3)
O3—Cu1—N1—N2	1.11 (13)	C2—C1—C6—O2	179.32 (18)
C7—N1—N2—C9	−176.51 (19)	O1—C1—C6—C5	179.8 (2)
Cu1—N1—N2—C9	−0.8 (2)	C2—C1—C6—C5	0.4 (3)
Cu1—O4—N3—O5	−171.45 (16)	N2—N1—C7—C2	179.38 (18)
Cu1—O4—N3—O6	8.3 (2)	Cu1—N1—C7—C2	4.5 (3)
Cu1—O1—C1—C2	−5.8 (3)	C3—C2—C7—N1	−178.50 (19)
Cu1—O1—C1—C6	174.91 (14)	C1—C2—C7—N1	0.8 (3)
O1—C1—C2—C3	179.18 (19)	Cu1—O3—C9—N2	1.2 (3)
C6—C1—C2—C3	−1.5 (3)	Cu1—O3—C9—C10	−177.50 (16)
O1—C1—C2—C7	−0.1 (3)	N1—N2—C9—O3	−0.3 (3)
C6—C1—C2—C7	179.19 (18)	N1—N2—C9—C10	178.48 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O7	0.86	1.95	2.801 (3)	174
O7—H1O···O1i	0.92	2.40	3.271 (3)	159
O7—H1O···O2i	0.92	2.42	3.050 (3)	126
O7—H2O···O5ii	0.92	2.08	2.984 (3)	167

Table 1

Selected bond lengths (Å)

Cu1—N1	1.9134 (18)
Cu1—O1	1.8798 (15)
Cu1—O3	1.9730 (16)
Cu1—O4	1.9663 (16)
Cu1—O6	2.559 (2)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O7	0.86	1.95	2.801 (3)	174
O7—H1O⋯O1i	0.92	2.40	3.271 (3)	159
O7—H1O⋯O2i	0.92	2.42	3.050 (3)	126
O7—H2O⋯O5ii	0.92	2.08	2.984 (3)	167

Symmetry codes: (i) ; (ii) .