{2-Hydr­oxy-N′-[1-(2-oxidophenyl)ethyl­idene]benzohydrazidato}morpholinecopper(II)

Lin, S.-Z.; Jia, R.-K.; Yuan, Y.-L.; Zhan, P.

doi:10.1107/S1600536809042810

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 11| November 2009| Page m1422

https://doi.org/10.1107/S1600536809042810

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{2-Hydroxy-N′-[1-(2-oxidophenyl)ethylidene]benzohydrazidato}morpholinecopper(II)

Song-Zhu Lin,^a ^* Ruo-Kun Jia,^a Yan-Lin Yuan ^a and Peng Zhan ^a

^aChemical Engineering Institute, Northeast Dianli University, Jilin, Jilin 132012, People's Republic of China
^*Correspondence e-mail: songzhulin@163.com

(Received 16 October 2009; accepted 18 October 2009; online 23 October 2009)

The Cu^II ion in the title complex, [Cu(C₁₅H₁₂N₂O₃)(C₄H₉NO)], is coordinated by one carbonyl O atom, one hydrazine N atom and one phenolate O atom from the doubly deprotonated tridentate ligand and one N atom from a morpholine molecule, forming a distorted trans-CuN₂O₂ square-planar coordination geometry. An intramolecular O—H⋯N hydrogen bond occurs within the ligand, generating an S(6) ring.

Related literature

For background to aroylhydrazone derivatives, see: Singh (1992 ); Liu et al. (2003 ); Bai et al. (2005 ). For related structures, see: Gatto et al. (2004 ); Huo et al. (2004 ); Chen et al. (2009 ).

Experimental

Crystal data

[Cu(C₁₅H₁₂N₂O₃)(C₄H₉NO)]
M_r = 418.93
Monoclinic, P 2₁ /n
a = 9.220 (4) Å
b = 17.616 (9) Å
c = 12.023 (6) Å
β = 112.257 (14)°
V = 1807.4 (15) Å³
Z = 4
Mo Kα radiation
μ = 1.24 mm⁻¹
T = 293 K
0.26 × 0.17 × 0.14 mm

Data collection

Rigaku Weissenberg IP diffractometer
Absorption correction: multi-scan (TEXRAY; Molecular Structure Corporation, 1999 ) T_min = 0.769, T_max = 0.837
16528 measured reflections
4032 independent reflections
3273 reflections with I > 2σ(I)
R_int = 0.049

Refinement

R[F² > 2σ(F²)] = 0.034
wR(F²) = 0.089
S = 1.05
4032 reflections
246 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Selected bond lengths (Å)

Cu1—O3	1.8702 (17)
Cu1—O2	1.9208 (16)
Cu1—N2	1.9409 (18)
Cu1—N3	2.0308 (19)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1	0.82	1.87	2.588 (3)	146

Data collection: TEXRAY (Molecular Structure Corporation, 1999); cell refinement: TEXRAY; data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536809042810/hb5147sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536809042810/hb5147Isup2.hkl

checkCIF report

Comment top

In the past decade, much attention has been focused on the study of aroylhydrazones derivative with aryl, aroyl and heteroaroyl Schiff bases due to their coordination abilities to metal ions (Singh et al., 1992; Liu et al., 2003; Bai et al., 2005). Ongoing the study of aroylhydrazone complexes, we report here the synthesis and crystal structure of a new complex with 2-hydroxy-N'- (2-oxyphenyl-ethylidene)benzohydrazidate(2-) ligand (Fig. 1).

The title complex, (I), contains one copper(II) center having distorted quadrilateral coordination environment, one O,N,O'-tridentate ligand molecule and one coordinated morpholine molecule. There exists one intramolecular phenol-hydrazone O—H···N hydrogen bond in each ligand, forming a six-membered ring.

Related literature top

For background to aroylhydrazone derivatives, see: Singh et al. (1992); Liu et al. (2003); Bai et al. (2005). For related structures, see: Gatto et al. (2004); Huo et al. (2004); Chen et al. (2009).

Experimental top

The ligand was prepared by the reaction of 2-hydroxyacetophenone and salicylhydrazine in a molar ratio of 1:1 under reflux in ethanol for 2 h. The white precipitate was collected, washed several times with ethanol and dried in vacuo (yield 79%). Morpholine (3 ml) was dropped into the mixture of 2-hydroxy-N'-(2-oxyphenyl- ethylidene)benzohydrazide (27 mg, 0.1 mmol) and Cu(Ac)₂.2H₂O (21 mg, 0.1 mmol) in methanol (10 ml). After stirring for 5 h, the reaction mixture was filtered and left to stand at room temperature. Green prisms of (I) were obtained by slow evaporation after 10 d. Analysis calculated for C₁₉H₂₁N₃O₄Cu: C 54.47, H 5.05, N 10.03%; found: C 53.99, H 5.01, N 10.29%.

Structure description top

Computing details top

Data collection: TEXRAY (Molecular Structure Corporation, 1999); cell refinement: TEXRAY (Molecular Structure Corporation, 1999); data reduction: TEXSAN (Molecular Structure Corporation, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of (I), showing displacement ellipsoids at the 30% probability level for non-H atoms. Dashed lines indicate hydrogen bonding. Only H atoms involved in hydrogen bonds have been included.

{2-Hydroxy-N'-[1-(2- oxidophenyl)ethylidene]benzohydrazidato}morpholinecopper(II) top

Crystal data top

[Cu(C₁₅H₁₂N₂O₃)(C₄H₉NO)]	F(000) = 868
M_r = 418.93	D_x = 1.540 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4032 reflections
a = 9.220 (4) Å	θ = 3.3–27.5°
b = 17.616 (9) Å	µ = 1.24 mm⁻¹
c = 12.023 (6) Å	T = 293 K
β = 112.257 (14)°	Prism, green
V = 1807.4 (15) Å³	0.26 × 0.17 × 0.14 mm
Z = 4

Data collection top

Rigaku Weissenberg IP diffractometer	4032 independent reflections
Radiation source: fine-focus sealed tube	3273 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.049
ω scans	θ_max = 27.5°, θ_min = 3.3°
Absorption correction: multi-scan (TEXRAY; Molecular Structure Corporation, 1999)	h = −11→10
T_min = 0.769, T_max = 0.837	k = −22→22
16528 measured reflections	l = −14→15

Refinement top

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)] = 0.034	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.089	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.042P)² + 0.6843P] where P = (F_o² + 2F_c²)/3
4032 reflections	(Δ/σ)_max = 0.001
246 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

[Cu(C₁₅H₁₂N₂O₃)(C₄H₉NO)]	V = 1807.4 (15) Å³
M_r = 418.93	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.220 (4) Å	µ = 1.24 mm⁻¹
b = 17.616 (9) Å	T = 293 K
c = 12.023 (6) Å	0.26 × 0.17 × 0.14 mm
β = 112.257 (14)°

Data collection top

Rigaku Weissenberg IP diffractometer	4032 independent reflections
Absorption correction: multi-scan (TEXRAY; Molecular Structure Corporation, 1999)	3273 reflections with I > 2σ(I)
T_min = 0.769, T_max = 0.837	R_int = 0.049
16528 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.089	H-atom parameters constrained
S = 1.05	Δρ_max = 0.35 e Å⁻³
4032 reflections	Δρ_min = −0.47 e Å⁻³
246 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Cu1	0.35584 (3)	0.512750 (15)	0.55888 (2)	0.03343 (10)
O1	−0.2016 (2)	0.39749 (11)	0.30393 (17)	0.0635 (5)
H1A	−0.1404	0.4330	0.3147	0.064 (9)*
O2	0.24346 (16)	0.42406 (8)	0.57392 (13)	0.0392 (4)
O3	0.46114 (18)	0.59329 (10)	0.52104 (14)	0.0479 (4)
O4	0.7081 (2)	0.51533 (12)	0.97389 (16)	0.0626 (5)
N1	0.06587 (19)	0.46639 (10)	0.39142 (17)	0.0373 (4)
N2	0.17322 (19)	0.52585 (9)	0.41154 (16)	0.0334 (4)
N3	0.5322 (2)	0.49568 (9)	0.72070 (16)	0.0343 (4)
H3B	0.5980	0.4618	0.7068	0.042 (6)*
C1	−0.1317 (3)	0.34097 (13)	0.3828 (2)	0.0438 (5)
C2	0.0206 (2)	0.34834 (12)	0.4699 (2)	0.0369 (5)
C3	0.0825 (3)	0.28792 (13)	0.5489 (2)	0.0428 (5)
H3A	0.1829	0.2921	0.6075	0.051*
C4	−0.0011 (3)	0.22263 (14)	0.5418 (3)	0.0534 (6)
H4A	0.0428	0.1827	0.5946	0.064*
C5	−0.1511 (3)	0.21633 (16)	0.4560 (3)	0.0618 (7)
H5A	−0.2085	0.1722	0.4513	0.074*
C6	−0.2160 (3)	0.27518 (16)	0.3775 (3)	0.0583 (7)
H6A	−0.3174	0.2707	0.3205	0.070*
C7	0.1169 (2)	0.41671 (12)	0.4806 (2)	0.0356 (5)
C8	0.1354 (2)	0.58214 (12)	0.33475 (19)	0.0362 (5)
C9	0.2478 (2)	0.64281 (12)	0.34607 (19)	0.0361 (5)
C10	0.4016 (3)	0.64486 (12)	0.43607 (19)	0.0370 (5)
C11	0.5022 (3)	0.70507 (13)	0.4351 (2)	0.0482 (6)
H11A	0.6018	0.7072	0.4952	0.058*
C12	0.4580 (3)	0.76027 (14)	0.3488 (3)	0.0570 (7)
H12A	0.5275	0.7987	0.3494	0.068*
C13	0.3082 (4)	0.75849 (15)	0.2602 (3)	0.0619 (7)
H13A	0.2771	0.7958	0.2011	0.074*
C14	0.2067 (3)	0.70213 (14)	0.2596 (2)	0.0503 (6)
H14A	0.1065	0.7025	0.2002	0.060*
C15	−0.0237 (3)	0.58277 (16)	0.2353 (2)	0.0536 (6)
H15A	−0.0490	0.5326	0.2024	0.080*
H15B	−0.0235	0.6172	0.1735	0.080*
H15C	−0.1004	0.5989	0.2665	0.080*
C16	0.6283 (3)	0.56298 (15)	0.7719 (2)	0.0539 (7)
H16A	0.5626	0.6022	0.7849	0.065*
H16B	0.6706	0.5824	0.7149	0.065*
C17	0.7606 (3)	0.5460 (2)	0.8884 (2)	0.0656 (8)
H17A	0.8319	0.5104	0.8740	0.079*
H17B	0.8182	0.5924	0.9200	0.079*
C18	0.6243 (4)	0.44769 (19)	0.9289 (2)	0.0773 (10)
H18A	0.5881	0.4268	0.9885	0.093*
H18B	0.6941	0.4108	0.9153	0.093*
C19	0.4852 (3)	0.46037 (18)	0.8129 (2)	0.0630 (8)
H19A	0.4348	0.4121	0.7832	0.076*
H19B	0.4098	0.4928	0.8282	0.076*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.02910 (14)	0.03649 (15)	0.02903 (15)	−0.00266 (10)	0.00461 (11)	0.00205 (10)
O1	0.0410 (9)	0.0587 (11)	0.0667 (12)	−0.0113 (8)	−0.0069 (9)	0.0105 (9)
O2	0.0315 (8)	0.0406 (8)	0.0368 (8)	−0.0046 (6)	0.0032 (7)	0.0024 (6)
O3	0.0385 (8)	0.0521 (10)	0.0427 (9)	−0.0085 (7)	0.0035 (7)	0.0171 (7)
O4	0.0669 (12)	0.0777 (13)	0.0314 (9)	−0.0159 (10)	0.0053 (9)	−0.0069 (8)
N1	0.0294 (9)	0.0389 (10)	0.0378 (10)	−0.0020 (7)	0.0060 (8)	−0.0014 (8)
N2	0.0295 (8)	0.0347 (10)	0.0316 (9)	0.0004 (7)	0.0067 (7)	−0.0024 (7)
N3	0.0321 (9)	0.0344 (9)	0.0314 (9)	0.0001 (7)	0.0065 (8)	−0.0045 (7)
C1	0.0394 (12)	0.0444 (13)	0.0434 (13)	−0.0061 (9)	0.0111 (10)	−0.0073 (10)
C2	0.0326 (10)	0.0384 (11)	0.0383 (11)	−0.0029 (8)	0.0118 (9)	−0.0091 (9)
C3	0.0402 (12)	0.0424 (12)	0.0438 (13)	−0.0020 (9)	0.0138 (11)	−0.0039 (10)
C4	0.0618 (16)	0.0403 (13)	0.0558 (15)	−0.0078 (11)	0.0197 (13)	−0.0032 (11)
C5	0.0701 (18)	0.0481 (15)	0.0636 (17)	−0.0251 (13)	0.0212 (15)	−0.0121 (13)
C6	0.0494 (15)	0.0606 (16)	0.0532 (15)	−0.0206 (12)	0.0063 (13)	−0.0138 (13)
C7	0.0297 (10)	0.0382 (11)	0.0377 (11)	0.0000 (8)	0.0115 (9)	−0.0047 (9)
C8	0.0335 (11)	0.0416 (12)	0.0304 (10)	0.0084 (8)	0.0087 (9)	−0.0003 (8)
C9	0.0391 (11)	0.0350 (11)	0.0341 (11)	0.0086 (8)	0.0139 (9)	0.0012 (8)
C10	0.0416 (11)	0.0356 (11)	0.0345 (11)	0.0025 (8)	0.0151 (10)	0.0017 (9)
C11	0.0489 (13)	0.0413 (13)	0.0524 (14)	−0.0024 (10)	0.0170 (12)	0.0038 (10)
C12	0.0651 (17)	0.0374 (13)	0.0692 (17)	−0.0018 (11)	0.0262 (15)	0.0089 (12)
C13	0.0736 (18)	0.0452 (15)	0.0617 (17)	0.0103 (13)	0.0196 (15)	0.0198 (13)
C14	0.0526 (14)	0.0436 (14)	0.0478 (14)	0.0109 (11)	0.0112 (12)	0.0126 (11)
C15	0.0411 (13)	0.0613 (16)	0.0451 (14)	0.0045 (11)	0.0014 (11)	0.0107 (11)
C16	0.0597 (15)	0.0538 (15)	0.0383 (12)	−0.0212 (12)	0.0072 (12)	−0.0059 (10)
C17	0.0515 (15)	0.092 (2)	0.0416 (14)	−0.0220 (15)	0.0043 (13)	−0.0141 (14)
C18	0.100 (2)	0.068 (2)	0.0369 (14)	−0.0222 (17)	−0.0044 (16)	0.0128 (13)
C19	0.0653 (17)	0.0730 (18)	0.0367 (13)	−0.0284 (14)	0.0036 (13)	0.0081 (12)

Geometric parameters (Å, º) top

Cu1—O3	1.8702 (17)	C6—H6A	0.9300
Cu1—O2	1.9208 (16)	C8—C9	1.459 (3)
Cu1—N2	1.9409 (18)	C8—C15	1.501 (3)
Cu1—N3	2.0308 (19)	C9—C14	1.421 (3)
O1—C1	1.357 (3)	C9—C10	1.421 (3)
O1—H1A	0.8200	C10—C11	1.412 (3)
O2—C7	1.283 (3)	C11—C12	1.366 (3)
O3—C10	1.321 (3)	C11—H11A	0.9300
O4—C17	1.399 (4)	C12—C13	1.389 (4)
O4—C18	1.412 (4)	C12—H12A	0.9300
N1—C7	1.325 (3)	C13—C14	1.362 (4)
N1—N2	1.398 (2)	C13—H13A	0.9300
N2—C8	1.309 (3)	C14—H14A	0.9300
N3—C16	1.468 (3)	C15—H15A	0.9600
N3—C19	1.472 (3)	C15—H15B	0.9600
N3—H3B	0.9100	C15—H15C	0.9600
C1—C6	1.384 (3)	C16—C17	1.499 (4)
C1—C2	1.404 (3)	C16—H16A	0.9700
C2—C3	1.397 (3)	C16—H16B	0.9700
C2—C7	1.473 (3)	C17—H17A	0.9700
C3—C4	1.370 (3)	C17—H17B	0.9700
C3—H3A	0.9300	C18—C19	1.512 (4)
C4—C5	1.381 (4)	C18—H18A	0.9700
C4—H4A	0.9300	C18—H18B	0.9700
C5—C6	1.377 (4)	C19—H19A	0.9700
C5—H5A	0.9300	C19—H19B	0.9700

O3—Cu1—O2	171.23 (7)	C10—C9—C8	123.93 (19)
O3—Cu1—N2	92.21 (7)	O3—C10—C11	116.2 (2)
O2—Cu1—N2	82.54 (7)	O3—C10—C9	125.0 (2)
O3—Cu1—N3	92.53 (7)	C11—C10—C9	118.8 (2)
O2—Cu1—N3	93.11 (7)	C12—C11—C10	122.2 (2)
N2—Cu1—N3	174.38 (8)	C12—C11—H11A	118.9
C1—O1—H1A	109.5	C10—C11—H11A	118.9
C7—O2—Cu1	110.14 (14)	C11—C12—C13	119.4 (2)
C10—O3—Cu1	127.42 (14)	C11—C12—H12A	120.3
C17—O4—C18	109.6 (2)	C13—C12—H12A	120.3
C7—N1—N2	110.10 (17)	C14—C13—C12	120.1 (2)
C8—N2—N1	117.62 (17)	C14—C13—H13A	119.9
C8—N2—Cu1	129.87 (15)	C12—C13—H13A	119.9
N1—N2—Cu1	112.43 (13)	C13—C14—C9	122.7 (2)
C16—N3—C19	109.2 (2)	C13—C14—H14A	118.7
C16—N3—Cu1	114.77 (15)	C9—C14—H14A	118.7
C19—N3—Cu1	115.24 (15)	C8—C15—H15A	109.5
C16—N3—H3B	105.6	C8—C15—H15B	109.5
C19—N3—H3B	105.6	H15A—C15—H15B	109.5
Cu1—N3—H3B	105.6	C8—C15—H15C	109.5
O1—C1—C6	118.2 (2)	H15A—C15—H15C	109.5
O1—C1—C2	122.0 (2)	H15B—C15—H15C	109.5
C6—C1—C2	119.8 (2)	N3—C16—C17	112.2 (2)
C3—C2—C1	118.2 (2)	N3—C16—H16A	109.2
C3—C2—C7	119.06 (19)	C17—C16—H16A	109.2
C1—C2—C7	122.7 (2)	N3—C16—H16B	109.2
C4—C3—C2	121.5 (2)	C17—C16—H16B	109.2
C4—C3—H3A	119.3	H16A—C16—H16B	107.9
C2—C3—H3A	119.3	O4—C17—C16	112.2 (2)
C3—C4—C5	119.7 (3)	O4—C17—H17A	109.2
C3—C4—H4A	120.2	C16—C17—H17A	109.2
C5—C4—H4A	120.2	O4—C17—H17B	109.2
C6—C5—C4	120.2 (2)	C16—C17—H17B	109.2
C6—C5—H5A	119.9	H17A—C17—H17B	107.9
C4—C5—H5A	119.9	O4—C18—C19	112.3 (2)
C5—C6—C1	120.6 (2)	O4—C18—H18A	109.2
C5—C6—H6A	119.7	C19—C18—H18A	109.2
C1—C6—H6A	119.7	O4—C18—H18B	109.2
O2—C7—N1	124.6 (2)	C19—C18—H18B	109.2
O2—C7—C2	118.6 (2)	H18A—C18—H18B	107.9
N1—C7—C2	116.84 (19)	N3—C19—C18	111.6 (2)
N2—C8—C9	119.94 (18)	N3—C19—H19A	109.3
N2—C8—C15	119.1 (2)	C18—C19—H19A	109.3
C9—C8—C15	121.0 (2)	N3—C19—H19B	109.3
C14—C9—C10	116.8 (2)	C18—C19—H19B	109.3
C14—C9—C8	119.2 (2)	H19A—C19—H19B	108.0

O3—Cu1—O2—C7	−49.8 (5)	N2—N1—C7—C2	−176.95 (18)
N2—Cu1—O2—C7	3.75 (14)	C3—C2—C7—O2	−11.5 (3)
N3—Cu1—O2—C7	−179.83 (14)	C1—C2—C7—O2	168.8 (2)
O2—Cu1—O3—C10	65.8 (5)	C3—C2—C7—N1	168.0 (2)
N2—Cu1—O3—C10	12.8 (2)	C1—C2—C7—N1	−11.7 (3)
N3—Cu1—O3—C10	−164.2 (2)	N1—N2—C8—C9	−175.30 (18)
C7—N1—N2—C8	−176.03 (19)	Cu1—N2—C8—C9	8.3 (3)
C7—N1—N2—Cu1	1.0 (2)	N1—N2—C8—C15	4.2 (3)
O3—Cu1—N2—C8	−13.1 (2)	Cu1—N2—C8—C15	−172.20 (17)
O2—Cu1—N2—C8	173.9 (2)	N2—C8—C9—C14	177.9 (2)
N3—Cu1—N2—C8	134.4 (7)	C15—C8—C9—C14	−1.6 (3)
O3—Cu1—N2—N1	170.31 (14)	N2—C8—C9—C10	1.1 (3)
O2—Cu1—N2—N1	−2.64 (14)	C15—C8—C9—C10	−178.4 (2)
N3—Cu1—N2—N1	−42.2 (8)	Cu1—O3—C10—C11	172.81 (17)
O3—Cu1—N3—C16	25.97 (19)	Cu1—O3—C10—C9	−8.7 (3)
O2—Cu1—N3—C16	−160.75 (18)	C14—C9—C10—O3	−177.8 (2)
N2—Cu1—N3—C16	−121.6 (7)	C8—C9—C10—O3	−0.9 (4)
O3—Cu1—N3—C19	154.11 (19)	C14—C9—C10—C11	0.6 (3)
O2—Cu1—N3—C19	−32.60 (19)	C8—C9—C10—C11	177.5 (2)
N2—Cu1—N3—C19	6.6 (8)	O3—C10—C11—C12	176.9 (2)
O1—C1—C2—C3	178.8 (2)	C9—C10—C11—C12	−1.7 (4)
C6—C1—C2—C3	0.3 (4)	C10—C11—C12—C13	1.4 (4)
O1—C1—C2—C7	−1.4 (4)	C11—C12—C13—C14	0.0 (4)
C6—C1—C2—C7	−180.0 (2)	C12—C13—C14—C9	−1.0 (4)
C1—C2—C3—C4	0.6 (4)	C10—C9—C14—C13	0.7 (4)
C7—C2—C3—C4	−179.1 (2)	C8—C9—C14—C13	−176.3 (3)
C2—C3—C4—C5	−0.9 (4)	C19—N3—C16—C17	51.4 (3)
C3—C4—C5—C6	0.3 (4)	Cu1—N3—C16—C17	−177.45 (19)
C4—C5—C6—C1	0.6 (5)	C18—O4—C17—C16	59.0 (4)
O1—C1—C6—C5	−179.5 (3)	N3—C16—C17—O4	−56.9 (3)
C2—C1—C6—C5	−0.9 (4)	C17—O4—C18—C19	−58.7 (4)
Cu1—O2—C7—N1	−4.7 (3)	C16—N3—C19—C18	−50.8 (3)
Cu1—O2—C7—C2	174.76 (15)	Cu1—N3—C19—C18	178.3 (2)
N2—N1—C7—O2	2.6 (3)	O4—C18—C19—N3	55.9 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.82	1.87	2.588 (3)	146

Experimental details

Crystal data
Chemical formula	[Cu(C₁₅H₁₂N₂O₃)(C₄H₉NO)]
M_r	418.93
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	9.220 (4), 17.616 (9), 12.023 (6)
β (°)	112.257 (14)
V (Å³)	1807.4 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.24
Crystal size (mm)	0.26 × 0.17 × 0.14

Data collection
Diffractometer	Rigaku Weissenberg IP
Absorption correction	Multi-scan (TEXRAY; Molecular Structure Corporation, 1999)
T_min, T_max	0.769, 0.837
No. of measured, independent and observed [I > 2σ(I)] reflections	16528, 4032, 3273
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.089, 1.05
No. of reflections	4032
No. of parameters	246
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.47

Computer programs: TEXRAY (Molecular Structure Corporation, 1999), TEXSAN (Molecular Structure Corporation, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).

Selected bond lengths (Å) top

Cu1—O3	1.8702 (17)	Cu1—N2	1.9409 (18)
Cu1—O2	1.9208 (16)	Cu1—N3	2.0308 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.82	1.87	2.588 (3)	146

Acknowledgements

We thank the Northeast Dianli University for supporting this study.

References

Bai, Y., Dang, D. B., Duan, C. Y., Song, Y. & Meng, Q. J. (2005). Inorg. Chem. 44, 5972–5974. Web of Science CSD CrossRef PubMed CAS Google Scholar
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Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Gatto, C. C., Schulz-Lang, E., Kupfer, A., Hagenbach, A. & Abram, U. (2004). Z. Anorg. Allg. Chem. 630, 1286–1295. Web of Science CSD CrossRef CAS Google Scholar
Huo, L.-H., Lu, Z.-Z., Gao, S., Zhao, H. & Zhao, J.-G. (2004). Acta Cryst. E60, m1636–m1638. Web of Science CSD CrossRef IUCr Journals Google Scholar
Liu, L., Ji, Y.-L., Jia, D.-Z. & Yu, K.-B. (2003). Chin. J. Struct. Chem. 22, 568–572. CAS Google Scholar
Molecular Structure Corporation (1999). TEXRAY and TEXSAN. MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Singh, G. (1992). Synth. React. Inorg. Met.-Org. Chem. 22, 1605–1618. CrossRef CAS Web of Science Google Scholar

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

{2-Hydr­­oxy-N′-[1-(2-oxido­phenyl)ethyl­­idene]benzohydrazidato}morpholinecopper(II)

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

{2-Hydroxy-N′-[1-(2-oxidophenyl)ethylidene]benzohydrazidato}morpholinecopper(II)