[2,2'-Dihy-droxy-N,N-(3-hy-droxy-imino-pentane-2,4-di-yl)dibenzo-hydra-zid-ato]copper(II).

The Cu(II) atom in the title complex, [Cu(C(19)H(17)N(5)O(5))], is coordinated by two N atoms and two O atoms of one 2,2'-dihy-droxy-N(2),N(2)'-(3-hy-droxy-imino-pentane-2,4-di-yl)dibenzo-hydrazidate ligand, exhibiting a distorted square-planar geometry. The dihedral angle between the two benzene rings in the oxime hydrazone is 7.62 (15)°. The molecular configuration is stabilized by intramolecular O-H⋯N hydrogen bonds. Pairs of centrosymmetrically related molecules are linked into dimers by two inter-molecular C-H⋯O hydrogen bonds. Each dimer is further connected to four neighboring dimers via four O-H⋯O hydrogen bonds, forming an extended two-dimensional structure. The oxime O atom is disordered over two orientations in a 2:1 ratio.

Related literature

For the structural versatility and biological activity of oxime hydrazone compounds and their metal complexes, see: Marmion et al. (2004 ▶); Song et al. (2000 ▶); Xiao et al. (2004 ▶). For similar copper(II) complexes with Schiff bases, see: Suleiman Gwaram et al. (2010 ▶); Qin et al. (2010 ▶).

Experimental

Crystal data

[Cu(C19H17N5O5)]

M = 458.92

Monoclinic,

a = 8.7672 (5) Å

b = 19.0262 (11) Å

c = 11.6118 (6) Å

β = 91.437 (2)°

V = 1936.31 (19) Å3

Z = 4

Mo Kα radiation

μ = 1.17 mm−1

T = 293 K

0.52 × 0.22 × 0.15 mm

Data collection

Rigaku Weissenberg IP diffractometer

Absorption correction: multi-scan (TEXRAY; Molecular Structure Corporation, 1999 ▶) T min = 0.715, T max = 0.833

17167 measured reflections

4436 independent reflections

3065 reflections with I > 2σ(I)

R int = 0.037

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.079

S = 0.91

4436 reflections

282 parameters

H-atom parameters constrained

Δρmax = 0.39 e Å−3

Δρmin = −0.40 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: ORTEX (McArdle, 1995 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810040754/om2355sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810040754/om2355Isup2.hkl

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

[Cu(C19H17N5O5)]	F(000) = 940
Mr = 458.92	Dx = 1.574 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 4577 reflections
a = 8.7672 (5) Å	θ = 2.1–27.5°
b = 19.0262 (11) Å	µ = 1.17 mm−1
c = 11.6118 (6) Å	T = 293 K
β = 91.437 (2)°	Prism, blue
V = 1936.31 (19) Å3	0.52 × 0.22 × 0.15 mm
Z = 4

Rigaku Weissenberg IP diffractometer	4436 independent reflections
Radiation source: fine-focus sealed tube	3065 reflections with I > 2σ(I)
graphite	Rint = 0.037
ω scans	θmax = 27.5°, θmin = 2.1°
Absorption correction: multi-scan (TEXRAY; Molecular Structure Corporation, 1999)	h = 0→11
Tmin = 0.715, Tmax = 0.833	k = −24→24
17167 measured reflections	l = −15→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) = 0.079	H-atom parameters constrained
S = 0.91	w = 1/[σ2(Fo2) + (0.040P)2] where P = (Fo2 + 2Fc2)/3
4436 reflections	(Δ/σ)max = 0.002
282 parameters	Δρmax = 0.39 e Å−3
0 restraints	Δρmin = −0.40 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	Occ. (<1)
Cu1	0.24832 (3)	0.508624 (12)	0.47601 (2)	0.03770 (9)
N1	0.46486 (19)	0.53298 (9)	0.64875 (15)	0.0428 (4)
N2	0.36561 (18)	0.48024 (9)	0.61023 (14)	0.0380 (4)
N3	0.2905 (3)	0.30306 (12)	0.6725 (2)	0.0735 (7)
N4	0.13118 (18)	0.42316 (8)	0.47217 (14)	0.0364 (4)
N5	0.01862 (18)	0.42494 (9)	0.38607 (15)	0.0401 (4)
O1	0.6627 (2)	0.59621 (11)	0.78120 (17)	0.0805 (6)
H1A	0.6074	0.5640	0.7587	0.097*
O2	0.34881 (15)	0.59685 (7)	0.50147 (13)	0.0414 (3)
O3A	0.2209 (4)	0.24814 (15)	0.6492 (3)	0.0749 (8)	0.67
O3B	0.3899 (6)	0.2757 (2)	0.7190 (5)	0.0635 (15)	0.33
O4	0.12933 (16)	0.53067 (7)	0.33856 (12)	0.0414 (3)
O5	−0.16592 (19)	0.36688 (8)	0.24617 (14)	0.0604 (5)
H5B	−0.1070	0.3703	0.3019	0.072*
C1	0.6346 (3)	0.65344 (14)	0.7173 (2)	0.0581 (7)
C2	0.5294 (2)	0.65449 (12)	0.6241 (2)	0.0461 (5)
C3	0.5081 (3)	0.71686 (12)	0.5633 (2)	0.0594 (7)
H3A	0.4376	0.7182	0.5022	0.071*
C4	0.5894 (3)	0.77687 (15)	0.5916 (3)	0.0784 (9)
H4A	0.5743	0.8181	0.5498	0.094*
C5	0.6921 (4)	0.77491 (18)	0.6816 (3)	0.0911 (11)
H5A	0.7467	0.8153	0.7011	0.109*
C6	0.7166 (3)	0.71460 (19)	0.7439 (3)	0.0849 (10)
H6A	0.7882	0.7144	0.8044	0.102*
C7	0.4416 (2)	0.59175 (11)	0.58840 (18)	0.0386 (5)
C8	0.3669 (2)	0.42120 (11)	0.66539 (18)	0.0409 (5)
C9	0.2605 (2)	0.36376 (11)	0.62829 (19)	0.0405 (5)
C10	0.1317 (2)	0.37065 (10)	0.54304 (19)	0.0394 (5)
C11	0.0336 (2)	0.48128 (10)	0.31893 (17)	0.0355 (4)
C12	−0.0688 (2)	0.48412 (11)	0.21619 (17)	0.0402 (5)
C13	−0.1615 (3)	0.42678 (13)	0.1830 (2)	0.0485 (5)
C14	−0.2529 (3)	0.43151 (16)	0.0835 (2)	0.0647 (7)
H14A	−0.3146	0.3939	0.0613	0.078*
C15	−0.2519 (3)	0.49149 (17)	0.0182 (2)	0.0718 (8)
H15A	−0.3126	0.4939	−0.0485	0.086*
C16	−0.1628 (3)	0.54807 (16)	0.0496 (2)	0.0679 (7)
H16A	−0.1637	0.5886	0.0047	0.082*
C17	−0.0720 (3)	0.54442 (13)	0.14814 (19)	0.0510 (6)
H17A	−0.0120	0.5828	0.1695	0.061*
C18	0.4736 (3)	0.41084 (14)	0.7671 (2)	0.0635 (7)
H18A	0.4647	0.4498	0.8190	0.095*
H18B	0.5765	0.4079	0.7412	0.095*
H18C	0.4478	0.3682	0.8062	0.095*
C19	0.0055 (3)	0.31770 (13)	0.5377 (3)	0.0628 (7)
H19A	−0.0886	0.3407	0.5167	0.094*
H19B	−0.0038	0.2958	0.6117	0.094*
H19C	0.0278	0.2826	0.4812	0.094*

	U11	U22	U33	U12	U13	U23
Cu1	0.03850 (14)	0.03025 (14)	0.04393 (15)	−0.00304 (11)	−0.00734 (9)	0.00278 (11)
N1	0.0401 (9)	0.0385 (10)	0.0495 (11)	−0.0008 (8)	−0.0091 (8)	−0.0045 (8)
N2	0.0340 (8)	0.0354 (10)	0.0443 (10)	0.0032 (7)	−0.0031 (7)	−0.0007 (8)
N3	0.0906 (18)	0.0425 (13)	0.0885 (18)	0.0125 (12)	0.0220 (14)	0.0210 (12)
N4	0.0365 (9)	0.0305 (9)	0.0418 (10)	0.0005 (7)	−0.0045 (7)	−0.0002 (7)
N5	0.0402 (9)	0.0339 (9)	0.0459 (10)	−0.0028 (7)	−0.0059 (8)	−0.0011 (8)
O1	0.0776 (13)	0.0845 (15)	0.0776 (14)	−0.0080 (11)	−0.0329 (11)	−0.0108 (11)
O2	0.0395 (8)	0.0317 (8)	0.0527 (9)	−0.0020 (6)	−0.0074 (7)	0.0017 (6)
O3A	0.093 (2)	0.0467 (17)	0.084 (2)	0.0043 (15)	−0.0252 (17)	0.0092 (14)
O3B	0.072 (3)	0.037 (3)	0.079 (4)	0.012 (2)	−0.045 (3)	0.014 (2)
O4	0.0468 (8)	0.0340 (8)	0.0430 (8)	−0.0071 (7)	−0.0071 (6)	0.0029 (6)
O5	0.0683 (11)	0.0463 (10)	0.0655 (11)	−0.0133 (8)	−0.0179 (9)	−0.0114 (8)
C1	0.0483 (14)	0.0602 (17)	0.0656 (17)	−0.0051 (12)	−0.0011 (12)	−0.0208 (13)
C2	0.0377 (11)	0.0423 (13)	0.0586 (14)	−0.0036 (10)	0.0049 (10)	−0.0157 (11)
C3	0.0614 (16)	0.0400 (14)	0.0772 (18)	−0.0083 (12)	0.0089 (13)	−0.0106 (12)
C4	0.083 (2)	0.0457 (16)	0.107 (3)	−0.0180 (15)	0.0168 (19)	−0.0154 (16)
C5	0.083 (2)	0.068 (2)	0.123 (3)	−0.0347 (18)	0.013 (2)	−0.040 (2)
C6	0.0618 (19)	0.094 (3)	0.098 (2)	−0.0187 (18)	−0.0068 (17)	−0.044 (2)
C7	0.0328 (10)	0.0360 (11)	0.0471 (13)	0.0016 (8)	0.0023 (9)	−0.0067 (9)
C8	0.0383 (11)	0.0382 (11)	0.0461 (13)	0.0094 (9)	−0.0020 (9)	0.0026 (9)
C9	0.0414 (11)	0.0332 (11)	0.0468 (12)	0.0057 (9)	0.0012 (9)	0.0072 (9)
C10	0.0377 (11)	0.0288 (10)	0.0517 (13)	0.0036 (8)	0.0040 (9)	0.0010 (9)
C11	0.0362 (10)	0.0325 (10)	0.0377 (11)	0.0030 (8)	−0.0009 (8)	−0.0051 (8)
C12	0.0394 (11)	0.0439 (12)	0.0370 (11)	0.0012 (9)	−0.0011 (8)	−0.0068 (9)
C13	0.0475 (13)	0.0499 (14)	0.0479 (13)	−0.0009 (10)	−0.0040 (10)	−0.0118 (11)
C14	0.0592 (15)	0.076 (2)	0.0583 (16)	−0.0082 (14)	−0.0143 (12)	−0.0202 (15)
C15	0.0670 (17)	0.098 (2)	0.0495 (14)	−0.0008 (17)	−0.0213 (12)	−0.0039 (16)
C16	0.0711 (17)	0.082 (2)	0.0497 (15)	0.0027 (16)	−0.0104 (13)	0.0140 (14)
C17	0.0506 (13)	0.0555 (15)	0.0466 (13)	−0.0031 (11)	−0.0061 (10)	0.0035 (11)
C18	0.0716 (17)	0.0571 (16)	0.0605 (16)	0.0002 (13)	−0.0220 (13)	0.0119 (13)
C19	0.0526 (14)	0.0424 (14)	0.093 (2)	−0.0080 (11)	−0.0113 (14)	0.0233 (13)

Cu1—O2	1.9153 (13)	C4—C5	1.362 (4)
Cu1—N2	1.9230 (16)	C4—H4A	0.9300
Cu1—N4	1.9231 (16)	C5—C6	1.371 (5)
Cu1—O4	1.9308 (14)	C5—H5A	0.9300
N1—C7	1.333 (3)	C6—H6A	0.9300
N1—N2	1.395 (2)	C8—C9	1.493 (3)
N2—C8	1.293 (3)	C8—C18	1.501 (3)
N3—O3B	1.140 (4)	C9—C10	1.489 (3)
N3—O3A	1.236 (3)	C10—C19	1.497 (3)
N3—C9	1.288 (3)	C11—C12	1.476 (3)
N4—C10	1.294 (3)	C12—C17	1.393 (3)
N4—N5	1.388 (2)	C12—C13	1.408 (3)
N5—C11	1.334 (3)	C13—C14	1.392 (3)
O1—C1	1.337 (3)	C14—C15	1.370 (4)
O1—H1A	0.8200	C14—H14A	0.9300
O2—C7	1.284 (2)	C15—C16	1.374 (4)
O3A—O3B	1.752 (5)	C15—H15A	0.9300
O4—C11	1.277 (2)	C16—C17	1.379 (3)
O5—C13	1.356 (3)	C16—H16A	0.9300
O5—H5B	0.8200	C17—H17A	0.9300
C1—C6	1.398 (4)	C18—H18A	0.9600
C1—C2	1.404 (3)	C18—H18B	0.9600
C2—C3	1.391 (3)	C18—H18C	0.9600
C2—C7	1.474 (3)	C19—H19A	0.9600
C3—C4	1.381 (3)	C19—H19B	0.9600
C3—H3A	0.9300	C19—H19C	0.9600
O2—Cu1—N2	83.48 (6)	N2—C8—C9	119.70 (18)
O2—Cu1—N4	171.09 (7)	N2—C8—C18	120.1 (2)
N2—Cu1—N4	93.19 (7)	C9—C8—C18	120.22 (19)
O2—Cu1—O4	100.02 (6)	N3—C9—C10	119.2 (2)
N2—Cu1—O4	176.23 (6)	N3—C9—C8	114.9 (2)
N4—Cu1—O4	83.54 (6)	C10—C9—C8	125.81 (18)
C7—N1—N2	110.44 (16)	N4—C10—C9	118.78 (18)
C8—N2—N1	117.96 (17)	N4—C10—C19	120.15 (19)
C8—N2—Cu1	130.03 (15)	C9—C10—C19	121.07 (19)
N1—N2—Cu1	111.99 (13)	O4—C11—N5	124.12 (18)
O3B—N3—O3A	94.9 (3)	O4—C11—C12	120.09 (18)
O3B—N3—C9	138.1 (4)	N5—C11—C12	115.79 (18)
O3A—N3—C9	125.1 (3)	C17—C12—C13	118.7 (2)
C10—N4—N5	117.91 (17)	C17—C12—C11	119.46 (19)
C10—N4—Cu1	130.13 (14)	C13—C12—C11	121.9 (2)
N5—N4—Cu1	111.46 (12)	O5—C13—C14	118.6 (2)
C11—N5—N4	111.23 (16)	O5—C13—C12	121.8 (2)
C1—O1—H1A	109.5	C14—C13—C12	119.5 (2)
C7—O2—Cu1	109.58 (13)	C15—C14—C13	120.1 (2)
C11—O4—Cu1	109.08 (13)	C15—C14—H14A	119.9
C13—O5—H5B	109.5	C13—C14—H14A	119.9
O1—C1—C6	117.9 (3)	C14—C15—C16	121.1 (2)
O1—C1—C2	123.2 (2)	C14—C15—H15A	119.4
C6—C1—C2	118.9 (3)	C16—C15—H15A	119.4
C3—C2—C1	118.7 (2)	C15—C16—C17	119.6 (3)
C3—C2—C7	119.0 (2)	C15—C16—H16A	120.2
C1—C2—C7	122.2 (2)	C17—C16—H16A	120.2
C4—C3—C2	121.5 (3)	C16—C17—C12	121.0 (2)
C4—C3—H3A	119.2	C16—C17—H17A	119.5
C2—C3—H3A	119.2	C12—C17—H17A	119.5
C5—C4—C3	119.1 (3)	C8—C18—H18A	109.5
C5—C4—H4A	120.4	C8—C18—H18B	109.5
C3—C4—H4A	120.4	H18A—C18—H18B	109.5
C4—C5—C6	121.3 (3)	C8—C18—H18C	109.5
C4—C5—H5A	119.3	H18A—C18—H18C	109.5
C6—C5—H5A	119.3	H18B—C18—H18C	109.5
C5—C6—C1	120.5 (3)	C10—C19—H19A	109.5
C5—C6—H6A	119.8	C10—C19—H19B	109.5
C1—C6—H6A	119.8	H19A—C19—H19B	109.5
O2—C7—N1	124.22 (19)	C10—C19—H19C	109.5
O2—C7—C2	118.43 (19)	H19A—C19—H19C	109.5
N1—C7—C2	117.36 (19)	H19B—C19—H19C	109.5
C7—N1—N2—C8	−175.43 (18)	Cu1—N2—C8—C9	−2.6 (3)
C7—N1—N2—Cu1	5.9 (2)	N1—N2—C8—C18	−0.3 (3)
O2—Cu1—N2—C8	177.17 (19)	Cu1—N2—C8—C18	178.08 (16)
N4—Cu1—N2—C8	5.46 (19)	O3B—N3—C9—C10	160.8 (5)
O2—Cu1—N2—N1	−4.33 (12)	O3A—N3—C9—C10	0.8 (4)
N4—Cu1—N2—N1	−176.04 (13)	O3B—N3—C9—C8	−16.5 (6)
N2—Cu1—N4—C10	4.20 (19)	O3A—N3—C9—C8	−176.5 (3)
O4—Cu1—N4—C10	−177.69 (19)	N2—C8—C9—N3	166.7 (2)
N2—Cu1—N4—N5	175.78 (13)	C18—C8—C9—N3	−14.0 (3)
O4—Cu1—N4—N5	−6.10 (12)	N2—C8—C9—C10	−10.4 (3)
C10—N4—N5—C11	−179.12 (18)	C18—C8—C9—C10	168.9 (2)
Cu1—N4—N5—C11	8.1 (2)	N5—N4—C10—C9	173.72 (17)
N2—Cu1—O2—C7	1.81 (13)	Cu1—N4—C10—C9	−15.1 (3)
O4—Cu1—O2—C7	−176.79 (13)	N5—N4—C10—C19	−5.6 (3)
C9—N3—O3A—O3B	166.8 (5)	Cu1—N4—C10—C19	165.55 (17)
C9—N3—O3B—O3A	−163.7 (6)	N3—C9—C10—N4	−157.7 (2)
O2—Cu1—O4—C11	−169.01 (12)	C8—C9—C10—N4	19.3 (3)
N4—Cu1—O4—C11	2.74 (13)	N3—C9—C10—C19	21.6 (3)
O1—C1—C2—C3	179.8 (2)	C8—C9—C10—C19	−161.4 (2)
C6—C1—C2—C3	−1.4 (4)	Cu1—O4—C11—N5	1.5 (2)
O1—C1—C2—C7	−0.6 (4)	Cu1—O4—C11—C12	−178.11 (14)
C6—C1—C2—C7	178.3 (2)	N4—N5—C11—O4	−6.6 (3)
C1—C2—C3—C4	0.9 (4)	N4—N5—C11—C12	172.98 (16)
C7—C2—C3—C4	−178.7 (2)	O4—C11—C12—C17	−7.1 (3)
C2—C3—C4—C5	−0.4 (4)	N5—C11—C12—C17	173.30 (19)
C3—C4—C5—C6	0.3 (5)	O4—C11—C12—C13	171.42 (19)
C4—C5—C6—C1	−0.8 (5)	N5—C11—C12—C13	−8.2 (3)
O1—C1—C6—C5	−179.8 (3)	C17—C12—C13—O5	−178.9 (2)
C2—C1—C6—C5	1.3 (4)	C11—C12—C13—O5	2.6 (3)
Cu1—O2—C7—N1	1.3 (2)	C17—C12—C13—C14	0.3 (3)
Cu1—O2—C7—C2	−179.02 (15)	C11—C12—C13—C14	−178.2 (2)
N2—N1—C7—O2	−4.9 (3)	O5—C13—C14—C15	179.5 (2)
N2—N1—C7—C2	175.42 (17)	C12—C13—C14—C15	0.3 (4)
C3—C2—C7—O2	0.4 (3)	C13—C14—C15—C16	−0.6 (4)
C1—C2—C7—O2	−179.2 (2)	C14—C15—C16—C17	0.4 (4)
C3—C2—C7—N1	−179.9 (2)	C15—C16—C17—C12	0.2 (4)
C1—C2—C7—N1	0.4 (3)	C13—C12—C17—C16	−0.5 (3)
N1—N2—C8—C9	178.94 (17)	C11—C12—C17—C16	178.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···N1	0.82	1.86	2.586 (2)	147
O5—H5B···N5	0.82	1.79	2.519 (2)	148
C19—H19A···O2i	0.96	2.58	3.525 (3)	170
O3A—H···O5ii	.	.	2.643 (3)	.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯N1	0.82	1.86	2.586 (2)	147
O5—H5B⋯N5	0.82	1.79	2.519 (2)	148
C19—H19A⋯O2i	0.96	2.58	3.525 (3)	170
O3A⋯O5ii			2.643 (3)

Symmetry codes: (i) ; (ii) .