{2-Hydr-oxy-N'-[1-(2-oxidophenyl)ethyl-idene]benzohydrazidato}morpholinecopper(II).

The Cu(II) ion in the title complex, [Cu(C(15)H(12)N(2)O(3))(C(4)H(9)NO)], 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 mol-ecule, forming a distorted trans-CuN(2)O(2) square-planar coordination geometry. An intra-molecular 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 = 418.93

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.089

S = 1.05

4032 reflections

246 parameters

H-atom parameters constrained

Δρmax = 0.35 e Å−3

Δρmin = −0.47 e Å−3

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.

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

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809042810/hb5147Isup2.hkl

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

[Cu(C15H12N2O3)(C4H9NO)]	F(000) = 868
Mr = 418.93	Dx = 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

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

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(Fo2) + (0.042P)2 + 0.6843P] where P = (Fo2 + 2Fc2)/3
4032 reflections	(Δ/σ)max = 0.001
246 parameters	Δρmax = 0.35 e Å−3
0 restraints	Δρmin = −0.47 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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