{(E)-4-Hy-droxy-N'-[phen-yl(pyridin-2-yl-κN)methyl-idene]benzohydrazide-κN',O}bis-(nitrato-κO,O')copper(II).

In the title compound, [Cu(NO(3))(2)(C(19)H(15)N(3)O(2))], the coordination geometry around the Cu(II) ion can be described as distorted square-pyramidal, with two N atoms and one O atom from an (E)-4-hy-droxy-N'-[phen-yl(pyridin-2-yl)methyl-ene]benzohydrazide ligand and one nitrate O atom in the basal plane and one nitrate O atom at the apical site. The other two nitrate O atoms also bind to the Cu atom with long Cu-O distances [2.607 (4) and 2.853 (5) Å]. The crystal packing is stabilized by inter-molecular N-H⋯O and O-H⋯O hydrogen bonds.

Related literature

For background to aroylhydrazones, see: Craliz et al. (1955 ▶). For pharmacological and catalytic applications of aroylhydrazones, see: Hosseini Monfared et al. (2010 ▶). For related structures, see: Huo et al. (2004 ▶); Kong et al. (2009 ▶); Mohd Lair et al. (2010 ▶); Shit et al. (2009 ▶); Yin (2008 ▶). For van der Waals radii, see: Bondi (1964 ▶).

Experimental

Crystal data

[Cu(NO3)2(C19H15N3O2)]

M = 504.91

Triclinic,

a = 9.881 (2) Å

b = 10.373 (2) Å

c = 11.964 (2) Å

α = 102.51 (3)°

β = 105.07 (3)°

γ = 111.16 (3)°

V = 1036.6 (6) Å3

Z = 2

Mo Kα radiation

μ = 1.11 mm−1

T = 298 K

0.30 × 0.15 × 0.10 mm

Data collection

Stoe IPDS 2T diffractometer

Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005 ▶) T min = 0.731, T max = 0.897

11512 measured reflections

5533 independent reflections

4123 reflections with I > 2σ(I)

R int = 0.099

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.197

S = 1.13

5533 reflections

303 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.84 e Å−3

Δρmin = −0.64 e Å−3

Data collection: X-AREA (Stoe & Cie, 2005 ▶); cell refinement: X-AREA; data reduction: X-AREA; 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: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811055772/hy2498sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811055772/hy2498Isup2.hkl

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

[Cu(NO3)2(C19H15N3O2)]	Z = 2
Mr = 504.91	F(000) = 514
Triclinic, P1	Dx = 1.618 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.881 (2) Å	Cell parameters from 5533 reflections
b = 10.373 (2) Å	θ = 1.9–29.2°
c = 11.964 (2) Å	µ = 1.11 mm−1
α = 102.51 (3)°	T = 298 K
β = 105.07 (3)°	Needle, green
γ = 111.16 (3)°	0.30 × 0.15 × 0.10 mm
V = 1036.6 (6) Å3

Stoe IPDS 2T diffractometer	5533 independent reflections
Radiation source: fine-focus sealed tube	4123 reflections with I > 2σ(I)
graphite	Rint = 0.099
Detector resolution: 0.15 mm pixels mm-1	θmax = 29.2°, θmin = 1.9°
rotation method scans	h = −13→13
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005)	k = −13→14
Tmin = 0.731, Tmax = 0.897	l = −16→16
11512 measured reflections

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.197	H atoms treated by a mixture of independent and constrained refinement
S = 1.13	w = 1/[σ2(Fo2) + (0.1213P)2] where P = (Fo2 + 2Fc2)/3
5533 reflections	(Δ/σ)max < 0.001
303 parameters	Δρmax = 0.84 e Å−3
1 restraint	Δρmin = −0.64 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	0.70675 (5)	−0.09738 (4)	0.74518 (4)	0.03884 (16)
O1	0.7184 (4)	−0.2036 (3)	0.5904 (2)	0.0440 (6)
O2	0.6844 (5)	−0.4026 (4)	0.0445 (3)	0.0650 (9)
H2A	0.7540	−0.3520	0.0256	0.098*
O3	0.4467 (4)	−0.2228 (3)	0.6994 (3)	0.0566 (7)
O4	0.2388 (4)	−0.1955 (4)	0.6201 (4)	0.0750 (10)
O5	0.4417 (5)	−0.0900 (5)	0.5848 (4)	0.0811 (12)
O6	0.7259 (3)	−0.2248 (3)	0.8443 (3)	0.0461 (6)
O7	0.9656 (4)	−0.1034 (4)	0.8623 (3)	0.0595 (8)
O8	0.9127 (4)	−0.2510 (4)	0.9654 (3)	0.0644 (9)
N1	0.7192 (4)	0.0659 (3)	0.8753 (3)	0.0409 (6)
N2	0.7711 (3)	0.0601 (3)	0.6788 (2)	0.0356 (5)
N3	0.7779 (4)	0.0173 (3)	0.5644 (3)	0.0400 (6)
N4	0.3756 (4)	−0.1701 (3)	0.6356 (3)	0.0455 (7)
N5	0.8729 (4)	−0.1919 (4)	0.8921 (3)	0.0430 (6)
C1	0.6978 (5)	0.0614 (5)	0.9806 (4)	0.0528 (9)
H1	0.6719	−0.0267	0.9963	0.063*
C2	0.7131 (7)	0.1835 (6)	1.0667 (4)	0.0654 (12)
H2	0.6984	0.1783	1.1396	0.078*
C3	0.7503 (7)	0.3120 (6)	1.0427 (5)	0.0703 (14)
H3	0.7574	0.3945	1.0982	0.084*
C4	0.7777 (6)	0.3203 (5)	0.9357 (4)	0.0529 (9)
H4	0.8072	0.4085	0.9202	0.063*
C5	0.7601 (4)	0.1944 (4)	0.8529 (3)	0.0389 (7)
C6	0.7855 (4)	0.1873 (4)	0.7353 (3)	0.0365 (6)
C7	0.8239 (4)	0.3152 (3)	0.6936 (3)	0.0371 (6)
C8	0.7251 (5)	0.3824 (4)	0.6785 (4)	0.0507 (9)
H8	0.6321	0.3449	0.6917	0.061*
C9	0.7662 (6)	0.5059 (5)	0.6437 (5)	0.0605 (11)
H9	0.6987	0.5493	0.6313	0.073*
C10	0.9046 (6)	0.5646 (5)	0.6275 (4)	0.0602 (11)
H10	0.9319	0.6492	0.6066	0.072*
C11	1.0036 (6)	0.4994 (5)	0.6419 (4)	0.0571 (10)
H11	1.0977	0.5394	0.6308	0.068*
C12	0.9617 (5)	0.3721 (4)	0.6734 (4)	0.0480 (8)
H12	1.0267	0.3257	0.6809	0.058*
C13	0.7418 (4)	−0.1287 (4)	0.5217 (3)	0.0378 (7)
C14	0.7340 (4)	−0.1929 (4)	0.3982 (3)	0.0372 (6)
C15	0.7989 (5)	−0.1090 (4)	0.3319 (4)	0.0463 (8)
H15	0.8528	−0.0070	0.3681	0.056*
C16	0.7840 (5)	−0.1755 (4)	0.2136 (4)	0.0464 (8)
H16	0.8290	−0.1188	0.1708	0.056*
C17	0.7007 (5)	−0.3293 (4)	0.1578 (3)	0.0449 (8)
C18	0.6355 (5)	−0.4144 (4)	0.2234 (4)	0.0474 (8)
H18	0.5798	−0.5162	0.1867	0.057*
C19	0.6544 (4)	−0.3464 (4)	0.3427 (3)	0.0420 (7)
H19	0.6136	−0.4032	0.3869	0.050*
H3A	0.762 (5)	0.060 (4)	0.510 (3)	0.042 (11)*

	U11	U22	U33	U12	U13	U23
Cu1	0.0537 (3)	0.0329 (2)	0.0368 (2)	0.02255 (18)	0.01981 (19)	0.01504 (16)
O1	0.0690 (16)	0.0362 (11)	0.0377 (12)	0.0304 (12)	0.0234 (12)	0.0157 (10)
O2	0.089 (2)	0.0500 (16)	0.0504 (16)	0.0209 (16)	0.0403 (17)	0.0075 (13)
O3	0.0596 (17)	0.0522 (16)	0.0630 (18)	0.0276 (14)	0.0200 (14)	0.0273 (14)
O4	0.0497 (18)	0.068 (2)	0.096 (3)	0.0300 (16)	0.0149 (18)	0.015 (2)
O5	0.069 (2)	0.079 (2)	0.095 (3)	0.0210 (19)	0.022 (2)	0.058 (2)
O6	0.0507 (14)	0.0443 (13)	0.0531 (15)	0.0243 (11)	0.0212 (12)	0.0265 (12)
O7	0.0511 (16)	0.0687 (19)	0.0625 (19)	0.0213 (14)	0.0227 (14)	0.0366 (16)
O8	0.073 (2)	0.082 (2)	0.066 (2)	0.0469 (19)	0.0297 (17)	0.0495 (19)
N1	0.0471 (16)	0.0399 (14)	0.0382 (14)	0.0211 (12)	0.0179 (12)	0.0125 (12)
N2	0.0459 (15)	0.0335 (12)	0.0286 (12)	0.0212 (11)	0.0110 (11)	0.0098 (10)
N3	0.0608 (18)	0.0340 (13)	0.0350 (14)	0.0275 (13)	0.0211 (13)	0.0146 (11)
N4	0.0447 (16)	0.0369 (14)	0.0431 (16)	0.0158 (12)	0.0061 (13)	0.0085 (12)
N5	0.0487 (16)	0.0496 (16)	0.0352 (14)	0.0258 (14)	0.0135 (12)	0.0182 (13)
C1	0.065 (3)	0.059 (2)	0.043 (2)	0.030 (2)	0.0250 (19)	0.0219 (18)
C2	0.090 (3)	0.078 (3)	0.047 (2)	0.048 (3)	0.038 (2)	0.023 (2)
C3	0.105 (4)	0.061 (3)	0.055 (3)	0.046 (3)	0.039 (3)	0.009 (2)
C4	0.070 (3)	0.046 (2)	0.0421 (19)	0.0315 (19)	0.0173 (18)	0.0065 (15)
C5	0.0451 (17)	0.0410 (16)	0.0310 (15)	0.0231 (14)	0.0115 (13)	0.0093 (12)
C6	0.0421 (17)	0.0336 (14)	0.0368 (15)	0.0208 (13)	0.0139 (13)	0.0114 (12)
C7	0.0438 (17)	0.0306 (14)	0.0346 (15)	0.0192 (13)	0.0098 (13)	0.0079 (11)
C8	0.055 (2)	0.0444 (19)	0.064 (2)	0.0316 (17)	0.0240 (19)	0.0214 (18)
C9	0.082 (3)	0.049 (2)	0.067 (3)	0.043 (2)	0.026 (2)	0.026 (2)
C10	0.087 (3)	0.0409 (19)	0.053 (2)	0.026 (2)	0.025 (2)	0.0228 (17)
C11	0.061 (2)	0.053 (2)	0.054 (2)	0.0182 (19)	0.024 (2)	0.0221 (19)
C12	0.054 (2)	0.0459 (18)	0.052 (2)	0.0259 (16)	0.0228 (17)	0.0208 (16)
C13	0.0446 (17)	0.0338 (15)	0.0416 (17)	0.0217 (13)	0.0195 (14)	0.0132 (13)
C14	0.0446 (17)	0.0371 (15)	0.0349 (15)	0.0229 (13)	0.0159 (13)	0.0121 (12)
C15	0.064 (2)	0.0337 (15)	0.0471 (19)	0.0236 (15)	0.0256 (17)	0.0154 (14)
C16	0.060 (2)	0.0460 (18)	0.0426 (18)	0.0264 (17)	0.0242 (17)	0.0205 (15)
C17	0.053 (2)	0.0437 (18)	0.0387 (17)	0.0232 (16)	0.0193 (15)	0.0099 (14)
C18	0.055 (2)	0.0349 (16)	0.050 (2)	0.0165 (15)	0.0273 (17)	0.0083 (14)
C19	0.0496 (19)	0.0387 (16)	0.0449 (18)	0.0213 (15)	0.0246 (16)	0.0159 (14)

Cu1—N2	1.944 (3)	C4—C5	1.379 (5)
Cu1—N1	1.978 (3)	C4—H4	0.9300
Cu1—O6	1.983 (3)	C5—C6	1.483 (5)
Cu1—O1	1.993 (2)	C6—C7	1.475 (4)
Cu1—O3	2.268 (3)	C7—C12	1.383 (5)
O1—C13	1.256 (4)	C7—C8	1.388 (5)
O2—C17	1.339 (5)	C8—C9	1.386 (6)
O2—H2A	0.8200	C8—H8	0.9300
O3—N4	1.247 (4)	C9—C10	1.367 (7)
O4—N4	1.233 (5)	C9—H9	0.9300
O5—N4	1.232 (5)	C10—C11	1.373 (7)
O6—N5	1.295 (4)	C10—H10	0.9300
O7—N5	1.230 (4)	C11—C12	1.399 (6)
O8—N5	1.237 (4)	C11—H11	0.9300
N1—C1	1.339 (5)	C12—H12	0.9300
N1—C5	1.354 (5)	C13—C14	1.454 (5)
N2—C6	1.282 (4)	C14—C19	1.400 (5)
N2—N3	1.373 (4)	C14—C15	1.400 (5)
N3—C13	1.364 (4)	C15—C16	1.377 (5)
N3—H3A	0.88 (4)	C15—H15	0.9300
C1—C2	1.380 (6)	C16—C17	1.405 (5)
C1—H1	0.9300	C16—H16	0.9300
C2—C3	1.365 (7)	C17—C18	1.401 (5)
C2—H2	0.9300	C18—C19	1.378 (5)
C3—C4	1.389 (6)	C18—H18	0.9300
C3—H3	0.9300	C19—H19	0.9300
N2—Cu1—N1	80.16 (12)	C4—C5—C6	124.1 (3)
N2—Cu1—O6	158.77 (13)	N2—C6—C7	126.2 (3)
N1—Cu1—O6	97.76 (12)	N2—C6—C5	111.8 (3)
N2—Cu1—O1	79.23 (11)	C7—C6—C5	121.9 (3)
N1—Cu1—O1	159.40 (12)	C12—C7—C8	119.5 (3)
O6—Cu1—O1	101.39 (11)	C12—C7—C6	120.1 (3)
N2—Cu1—O3	116.69 (12)	C8—C7—C6	120.4 (3)
N1—Cu1—O3	90.60 (13)	C9—C8—C7	119.5 (4)
O6—Cu1—O3	84.35 (11)	C9—C8—H8	120.3
O1—Cu1—O3	98.75 (13)	C7—C8—H8	120.3
C13—O1—Cu1	113.6 (2)	C10—C9—C8	120.9 (4)
C17—O2—H2A	109.5	C10—C9—H9	119.6
N4—O3—Cu1	109.2 (2)	C8—C9—H9	119.6
N5—O6—Cu1	107.5 (2)	C9—C10—C11	120.3 (4)
C1—N1—C5	119.4 (3)	C9—C10—H10	119.8
C1—N1—Cu1	126.8 (3)	C11—C10—H10	119.8
C5—N1—Cu1	113.7 (2)	C10—C11—C12	119.5 (4)
C6—N2—N3	125.3 (3)	C10—C11—H11	120.3
C6—N2—Cu1	119.5 (2)	C12—C11—H11	120.3
N3—N2—Cu1	114.7 (2)	C7—C12—C11	120.2 (4)
C13—N3—N2	112.3 (3)	C7—C12—H12	119.9
C13—N3—H3A	118 (3)	C11—C12—H12	119.9
N2—N3—H3A	124 (3)	O1—C13—N3	119.5 (3)
O5—N4—O4	117.7 (4)	O1—C13—C14	121.7 (3)
O5—N4—O3	120.0 (4)	N3—C13—C14	118.9 (3)
O4—N4—O3	122.3 (4)	C19—C14—C15	118.9 (3)
O7—N5—O8	123.4 (4)	C19—C14—C13	117.8 (3)
O7—N5—O6	118.4 (3)	C15—C14—C13	123.3 (3)
O8—N5—O6	118.2 (3)	C16—C15—C14	120.8 (3)
N1—C1—C2	122.0 (4)	C16—C15—H15	119.6
N1—C1—H1	119.0	C14—C15—H15	119.6
C2—C1—H1	119.0	C15—C16—C17	119.8 (3)
C3—C2—C1	118.6 (4)	C15—C16—H16	120.1
C3—C2—H2	120.7	C17—C16—H16	120.1
C1—C2—H2	120.7	O2—C17—C18	116.6 (3)
C2—C3—C4	120.3 (4)	O2—C17—C16	123.4 (3)
C2—C3—H3	119.8	C18—C17—C16	119.9 (3)
C4—C3—H3	119.8	C19—C18—C17	119.6 (3)
C5—C4—C3	118.3 (4)	C19—C18—H18	120.2
C5—C4—H4	120.8	C17—C18—H18	120.2
C3—C4—H4	120.8	C18—C19—C14	120.9 (3)
N1—C5—C4	121.3 (3)	C18—C19—H19	119.5
N1—C5—C6	114.6 (3)	C14—C19—H19	119.5
N2—Cu1—O1—C13	−7.4 (3)	Cu1—N1—C5—C6	0.7 (4)
N1—Cu1—O1—C13	−7.8 (5)	C3—C4—C5—N1	−0.9 (7)
O6—Cu1—O1—C13	−165.8 (3)	C3—C4—C5—C6	−180.0 (4)
O3—Cu1—O1—C13	108.2 (3)	N3—N2—C6—C7	−5.0 (6)
N2—Cu1—O3—N4	−0.9 (3)	Cu1—N2—C6—C7	−176.1 (3)
N1—Cu1—O3—N4	78.4 (3)	N3—N2—C6—C5	175.6 (3)
O6—Cu1—O3—N4	176.1 (3)	Cu1—N2—C6—C5	4.4 (4)
O1—Cu1—O3—N4	−83.2 (3)	N1—C5—C6—N2	−3.2 (5)
N2—Cu1—O6—N5	−9.2 (4)	C4—C5—C6—N2	176.0 (4)
N1—Cu1—O6—N5	−92.0 (2)	N1—C5—C6—C7	177.3 (3)
O1—Cu1—O6—N5	80.4 (2)	C4—C5—C6—C7	−3.5 (6)
O3—Cu1—O6—N5	178.2 (2)	N2—C6—C7—C12	−58.8 (5)
N2—Cu1—N1—C1	−176.0 (4)	C5—C6—C7—C12	120.6 (4)
O6—Cu1—N1—C1	−17.4 (4)	N2—C6—C7—C8	123.5 (4)
O1—Cu1—N1—C1	−175.6 (4)	C5—C6—C7—C8	−57.1 (5)
O3—Cu1—N1—C1	67.0 (4)	C12—C7—C8—C9	−0.1 (6)
N2—Cu1—N1—C5	1.2 (3)	C6—C7—C8—C9	177.6 (4)
O6—Cu1—N1—C5	159.8 (3)	C7—C8—C9—C10	−1.9 (7)
O1—Cu1—N1—C5	1.6 (5)	C8—C9—C10—C11	1.9 (7)
O3—Cu1—N1—C5	−115.9 (3)	C9—C10—C11—C12	0.0 (7)
N1—Cu1—N2—C6	−3.3 (3)	C8—C7—C12—C11	2.0 (6)
O6—Cu1—N2—C6	−89.4 (4)	C6—C7—C12—C11	−175.7 (4)
O1—Cu1—N2—C6	176.9 (3)	C10—C11—C12—C7	−2.0 (7)
O3—Cu1—N2—C6	82.4 (3)	Cu1—O1—C13—N3	9.0 (4)
N1—Cu1—N2—N3	−175.4 (3)	Cu1—O1—C13—C14	−172.0 (3)
O6—Cu1—N2—N3	98.5 (4)	N2—N3—C13—O1	−5.0 (5)
O1—Cu1—N2—N3	4.8 (2)	N2—N3—C13—C14	176.1 (3)
O3—Cu1—N2—N3	−89.7 (3)	O1—C13—C14—C19	19.3 (5)
C6—N2—N3—C13	−173.3 (3)	N3—C13—C14—C19	−161.8 (3)
Cu1—N2—N3—C13	−1.7 (4)	O1—C13—C14—C15	−162.1 (4)
Cu1—O3—N4—O5	16.3 (5)	N3—C13—C14—C15	16.8 (5)
Cu1—O3—N4—O4	−164.1 (3)	C19—C14—C15—C16	0.5 (6)
Cu1—O6—N5—O7	−5.3 (4)	C13—C14—C15—C16	−178.0 (4)
Cu1—O6—N5—O8	174.7 (3)	C14—C15—C16—C17	1.0 (6)
C5—N1—C1—C2	1.3 (6)	C15—C16—C17—O2	−178.2 (4)
Cu1—N1—C1—C2	178.4 (4)	C15—C16—C17—C18	−1.1 (6)
N1—C1—C2—C3	0.4 (8)	O2—C17—C18—C19	177.0 (4)
C1—C2—C3—C4	−2.4 (9)	C16—C17—C18—C19	−0.3 (6)
C2—C3—C4—C5	2.6 (8)	C17—C18—C19—C14	1.8 (6)
C1—N1—C5—C4	−1.1 (6)	C15—C14—C19—C18	−1.9 (6)
Cu1—N1—C5—C4	−178.5 (3)	C13—C14—C19—C18	176.7 (4)
C1—N1—C5—C6	178.1 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O5i	0.88 (4)	2.20 (5)	2.866 (6)	132 (4)
N3—H3A···O4i	0.88 (4)	2.31 (4)	3.180 (5)	171 (3)
O2—H2A···O8ii	0.82	1.95	2.766 (5)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O5i	0.88 (4)	2.20 (5)	2.866 (6)	132 (4)
N3—H3A⋯O4i	0.88 (4)	2.31 (4)	3.180 (5)	171 (3)
O2—H2A⋯O8ii	0.82	1.95	2.766 (5)	174

Symmetry codes: (i) ; (ii) .