Chlorido(4-methylpyridin-2-amine-κN1)(2-{[(4-methylpyridin-2-yl)imino-κN]methyl}phenolato-κO)copper(II)

Bhagyaraju, B.; Sambasiva Rao, P.; Swu, T.

doi:10.1107/S1600536812047198

metal-organic compounds

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ISSN: 2056-9890

Volume 68| Part 12| December 2012| Page m1523

doi:10.1107/S1600536812047198

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Chlorido(4-methylpyridin-2-amine-κN¹)(2-{[(4-methylpyridin-2-yl)imino-κN]methyl}phenolato-κO)copper(II)

Bussa Bhagyaraju,^a P. Sambasiva Rao ^a ‡ and Toka Swu ^a ^*

^aDepartment of Chemistry, Pondicherry University, R.V. Nagar, Kalapet, Puducherry 605 014, India
^*Correspondence e-mail: tokaswu.che@pondiuni.edu.in

(Received 25 October 2012; accepted 16 November 2012; online 24 November 2012)

In the title complex, [Cu(C₁₃H₁₁N₂O)Cl(C₆H₈N₂)], the Cu^II atom adopts a distorted tetrahedral geometry being coordinated by the phenolic O atom and the azomethine N atom of the Schiff base ligand N-salicylidene 2-aminopyridine, and by the 2-aminopyridine N atom and a Cl atom. The pyridyl N atom of the Schiff base and the imino N atom of the 4-methyl-pyridine-2-ylimino ligand are not involved in the coordination. There is an intramolecular N—H⋯N hydrogen bond involving the pyridine N atom and the amino group of the 2-aminopyridine ligand. In the crystal, molecules are linked via N—H⋯Cl hydrogen bonds, forming chains propagating along [001].

Related literature

For the preparation of similar compounds, see: Miao et al. (2009 ); Parashar et al. (1988 ); Castineiras et al. (1989 ). For the crystal structures of related compounds, see: Castineiras et al. (1989); Miao et al. (2009).

Experimental

Crystal data

[Cu(C₁₃H₁₁N₂O)Cl(C₆H₈N₂)
M_r = 418.37
Monoclinic, P 2₁ /c
a = 17.443 (4) Å
b = 11.2197 (19) Å
c = 9.4435 (19) Å
β = 92.67 (2)°
V = 1846.1 (6) Å³
Z = 4
Mo Kα radiation
μ = 1.34 mm⁻¹
T = 300 K
0.40 × 0.40 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur, Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd., Yarnton, England.]$ ) T_min = 0.565, T_max = 1.000
7213 measured reflections
3339 independent reflections
2017 reflections with I > 2σ(I)
R_int = 0.063

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.114
S = 0.94
3339 reflections
243 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2NB⋯N3	0.85 (4)	2.27 (4)	3.039 (6)	150 (5)
N2—H2NA⋯Cl1ⁱ	0.86 (4)	2.44 (4)	3.305 (5)	179 (7)
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd., Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: OLEX2.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812047198/su2518sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812047198/su2518Isup2.hkl

checkCIF report

Comment top

The Schiff base, N-salicylidene 2-aminopyridine, has been widely studied as a potential tridentate ligand. For example, the complex Bis{2-[(2-pyridyl)iminomethyl]-phenolato}copper(II), has been prepared by (Miao et al., 2009), who reported that to a green solution of salicylaldehyde (0.19 mmol) and Cu(OAc)₂.H₂O (0.05 mmol) in ethanol they added slowly an enthanolic solution of 2-aminopyridine (0.22 mmol). The resulting mixture was allowed to stand and brown crystalline needles were obtained after 1 day. The same compound was prepared by an electrochemical method (Castineiras et al., 1989) and by a solution method (Parashar et al., 1988). We have used same procedure as (Miao et al., 2009), but using a 1:1:1 molar ratio that produced the yellow crystals of the title compound, whose crystal structure we report on herein.

In the title complex, Fig. 1, the copper atom has a slightly distorted tetahedral geometry. It coordinates to the phenolic atom O1 and the azomethine atom N4 of the Schiff base liagnd N-salicylidene 2-aminopyridine, and to the 2-aminopyridine atom N1 and a chlorine atom, Cl1. The Cu—O1 and Cu—N4 bond lengths are similar to those reported in related structures (Miao et al., 2009; Castineiras et al., 1989). The structure of the molecule is stablized by an intramolecular N-H..Cl hydrogen bond (Table 1).

In the crystal, the intermolecular N-H···Cl hydrogen bond (Fig. 2 and Table 1) plays an important role in linking the molecules to form chains propagating along the c axis, as shown in Fig. 3.

Related literature top

For the preparation of similar compounds, see: Miao et al. (2009); Parashar et al. (1988); Castineiras et al. (1989). For the crystal structures of related compounds, see: Castineiras et al. (1989); Miao et al. (2009).

Experimental top

A methanolic solution of 2-(((4-methyl-pyridine-2-yl)imino)methyl)phenol (0.01 moles) and 4-methylpyridin-2-amine (0.01 moles) was added slowly to a methanolic solution of copper chloride (0.01 moles). The resulting mixture was allowed to stand and yellow plate-like crystals were obtained after ca. 7 days.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009) and PLATON (Spek, 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).

Figures top

	Fig. 1. The molecular structure of title compound, showing the atom numbering. The displacement ellipsoids are drawn at the 50% probability level. The intramolecular N-H···Cl bond is shown as a dashed line (see Table 1 for details).
	Fig. 2. A view along b axis of the crystal packing of the title compound.
	Fig. 3. A view of the N-H···Cl hydrogen bonded chain structure propagating along the c axis direction (dashed line; see Table 1 for details).

Chlorido(4-methylpyridin-2-amine-κN¹)(2-{[(4-methylpyridin-2- yl)imino-κN]methyl}phenolato-κO)copper(II) top

Crystal data top

[Cu(C₁₃H₁₁N₂O)Cl(C₆H₈N₂)]	F(000) = 860
M_r = 418.37	D_x = 1.505 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71070 Å
Hall symbol: -P 2ybc	Cell parameters from 2251 reflections
a = 17.443 (4) Å	θ = 2.8–29.4°
b = 11.2197 (19) Å	µ = 1.34 mm⁻¹
c = 9.4435 (19) Å	T = 300 K
β = 92.67 (2)°	Plate, yellow
V = 1846.1 (6) Å³	0.4 × 0.4 × 0.06 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur, Eos diffractometer	3339 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2017 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.063
ω scans	θ_max = 25.3°, θ_min = 2.8°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	h = −14→20
T_min = 0.565, T_max = 1.000	k = −13→10
7213 measured reflections	l = −11→11

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	w = 1/[σ²(F_o²) + (0.0352P)²] where P = (F_o² + 2F_c²)/3
3339 reflections	(Δ/σ)_max = 0.001
243 parameters	Δρ_max = 0.40 e Å⁻³
2 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

[Cu(C₁₃H₁₁N₂O)Cl(C₆H₈N₂)]	V = 1846.1 (6) Å³
M_r = 418.37	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.443 (4) Å	µ = 1.34 mm⁻¹
b = 11.2197 (19) Å	T = 300 K
c = 9.4435 (19) Å	0.4 × 0.4 × 0.06 mm
β = 92.67 (2)°

Data collection top

Oxford Diffraction Xcalibur, Eos diffractometer	3339 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	2017 reflections with I > 2σ(I)
T_min = 0.565, T_max = 1.000	R_int = 0.063
7213 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	2 restraints
wR(F²) = 0.114	H atoms treated by a mixture of independent and constrained refinement
S = 0.94	Δρ_max = 0.40 e Å⁻³
3339 reflections	Δρ_min = −0.45 e Å⁻³
243 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Cu1	0.23453 (3)	0.51797 (4)	0.79066 (6)	0.0389 (2)
Cl1	0.13907 (8)	0.44704 (11)	0.91654 (15)	0.0642 (5)
O1	0.30823 (19)	0.6041 (3)	0.9125 (3)	0.0528 (13)
N1	0.3004 (2)	0.3846 (3)	0.7218 (4)	0.0385 (12)
N2	0.2006 (3)	0.2818 (4)	0.6107 (6)	0.079 (2)
N3	0.1439 (2)	0.5299 (3)	0.5301 (5)	0.0526 (16)
N4	0.2022 (2)	0.6618 (3)	0.6805 (4)	0.0367 (12)
C1	0.2746 (3)	0.2872 (4)	0.6490 (5)	0.0436 (17)
C2	0.3246 (3)	0.1932 (4)	0.6186 (5)	0.0432 (17)
C3	0.3996 (3)	0.1993 (4)	0.6589 (5)	0.0420 (17)
C4	0.4263 (3)	0.3013 (4)	0.7295 (5)	0.0476 (17)
C5	0.3758 (3)	0.3887 (4)	0.7583 (5)	0.0433 (17)
C6	0.4539 (3)	0.0991 (4)	0.6281 (5)	0.061 (2)
C7	0.1478 (3)	0.6438 (4)	0.5666 (5)	0.0389 (17)
C8	0.1030 (3)	0.7309 (4)	0.5036 (5)	0.0424 (17)
C9	0.0524 (3)	0.7024 (4)	0.3933 (5)	0.0476 (17)
C10	0.0505 (3)	0.5841 (4)	0.3494 (6)	0.067 (2)
C11	0.0968 (4)	0.5026 (5)	0.4217 (7)	0.077 (3)
C12	0.0006 (3)	0.7932 (5)	0.3246 (6)	0.066 (2)
C13	0.3222 (3)	0.7167 (4)	0.9098 (5)	0.0421 (17)
C14	0.2837 (3)	0.7994 (4)	0.8159 (5)	0.0406 (17)
C15	0.3030 (3)	0.9213 (4)	0.8254 (5)	0.0577 (19)
C16	0.3574 (4)	0.9616 (5)	0.9200 (6)	0.072 (3)
C17	0.3958 (3)	0.8815 (5)	1.0102 (6)	0.066 (2)
C18	0.3778 (3)	0.7637 (4)	1.0062 (5)	0.053 (2)
C19	0.2287 (3)	0.7673 (4)	0.7090 (5)	0.0428 (17)
H2NA	0.184 (3)	0.223 (3)	0.559 (5)	0.0950*
H2	0.30570	0.12630	0.57040	0.0520*
H2NB	0.177 (3)	0.348 (3)	0.618 (6)	0.0950*
H4	0.47800	0.30930	0.75630	0.0570*
H5	0.39440	0.45580	0.80650	0.0520*
H6A	0.42650	0.03750	0.57640	0.0920*
H6B	0.47520	0.06720	0.71560	0.0920*
H6C	0.49450	0.12870	0.57260	0.0920*
H8	0.10680	0.80920	0.53560	0.0510*
H10	0.01860	0.56040	0.27290	0.0800*
H11	0.09480	0.42360	0.39210	0.0930*
H12A	−0.02900	0.83080	0.39510	0.0990*
H12B	−0.03320	0.75510	0.25550	0.0990*
H12C	0.03080	0.85210	0.27880	0.0990*
H15	0.27770	0.97530	0.76500	0.0700*
H16	0.36900	1.04250	0.92470	0.0850*
H17	0.43420	0.90870	1.07380	0.0780*
H18	0.40330	0.71230	1.06970	0.0640*
H19	0.20910	0.82900	0.65230	0.0520*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.0416 (4)	0.0315 (3)	0.0429 (4)	0.0040 (3)	−0.0052 (3)	−0.0010 (3)
Cl1	0.0576 (10)	0.0592 (8)	0.0768 (10)	0.0139 (7)	0.0154 (8)	0.0244 (8)
O1	0.067 (3)	0.0363 (18)	0.053 (2)	0.0006 (16)	−0.0208 (19)	−0.0021 (17)
N1	0.035 (2)	0.034 (2)	0.046 (2)	−0.0017 (18)	−0.004 (2)	−0.0007 (19)
N2	0.043 (3)	0.052 (3)	0.139 (5)	0.006 (2)	−0.026 (3)	−0.049 (3)
N3	0.053 (3)	0.041 (2)	0.062 (3)	−0.003 (2)	−0.016 (2)	−0.006 (2)
N4	0.034 (2)	0.040 (2)	0.036 (2)	−0.0026 (18)	0.0004 (19)	0.0008 (19)
C1	0.037 (3)	0.040 (3)	0.053 (3)	−0.001 (2)	−0.005 (3)	−0.003 (3)
C2	0.045 (3)	0.040 (3)	0.044 (3)	0.003 (2)	−0.003 (3)	−0.005 (2)
C3	0.046 (3)	0.039 (3)	0.041 (3)	0.008 (2)	0.003 (3)	−0.001 (2)
C4	0.033 (3)	0.060 (3)	0.049 (3)	0.008 (3)	−0.006 (3)	0.000 (3)
C5	0.042 (3)	0.041 (3)	0.046 (3)	−0.008 (2)	−0.009 (3)	−0.003 (2)
C6	0.060 (4)	0.061 (3)	0.063 (4)	0.021 (3)	0.008 (3)	0.001 (3)
C7	0.038 (3)	0.042 (3)	0.037 (3)	−0.004 (2)	0.006 (2)	−0.004 (2)
C8	0.045 (3)	0.037 (3)	0.045 (3)	0.001 (2)	−0.001 (3)	0.005 (2)
C9	0.037 (3)	0.055 (3)	0.051 (3)	−0.003 (3)	0.004 (3)	0.015 (3)
C10	0.062 (4)	0.059 (4)	0.077 (4)	−0.010 (3)	−0.026 (3)	−0.006 (3)
C11	0.084 (5)	0.053 (3)	0.092 (5)	−0.005 (3)	−0.027 (4)	−0.015 (3)
C12	0.053 (4)	0.086 (4)	0.058 (4)	0.008 (3)	−0.011 (3)	0.013 (3)
C13	0.038 (3)	0.051 (3)	0.038 (3)	−0.005 (2)	0.008 (3)	−0.009 (3)
C14	0.048 (3)	0.037 (3)	0.037 (3)	−0.006 (2)	0.004 (3)	−0.009 (2)
C15	0.069 (4)	0.051 (3)	0.053 (3)	−0.014 (3)	0.002 (3)	−0.003 (3)
C16	0.084 (5)	0.068 (4)	0.062 (4)	−0.030 (4)	−0.001 (4)	−0.011 (3)
C17	0.065 (4)	0.083 (4)	0.049 (4)	−0.019 (3)	0.001 (3)	−0.026 (3)
C18	0.049 (4)	0.067 (4)	0.043 (3)	0.002 (3)	−0.008 (3)	−0.014 (3)
C19	0.041 (3)	0.046 (3)	0.042 (3)	0.001 (2)	0.007 (3)	0.005 (3)

Geometric parameters (Å, º) top

Cu1—Cl1	2.2368 (16)	C13—C18	1.402 (7)
Cu1—O1	1.942 (3)	C13—C14	1.429 (7)
Cu1—N1	2.013 (4)	C14—C19	1.407 (7)
Cu1—N3	2.865 (5)	C14—C15	1.410 (6)
Cu1—N4	1.987 (4)	C15—C16	1.351 (8)
O1—C13	1.287 (6)	C16—C17	1.389 (8)
N1—C1	1.357 (6)	C17—C18	1.359 (7)
N1—C5	1.345 (6)	C2—H2	0.9300
N2—C1	1.326 (7)	C4—H4	0.9300
N3—C7	1.325 (6)	C5—H5	0.9300
N3—C11	1.319 (8)	C6—H6A	0.9600
N4—C7	1.415 (6)	C6—H6B	0.9600
N4—C19	1.295 (6)	C6—H6C	0.9600
N2—H2NB	0.85 (4)	C8—H8	0.9300
N2—H2NA	0.86 (4)	C10—H10	0.9300
C1—C2	1.407 (7)	C11—H11	0.9300
C2—C3	1.347 (7)	C12—H12A	0.9600
C3—C6	1.507 (7)	C12—H12B	0.9600
C3—C4	1.394 (7)	C12—H12C	0.9600
C4—C5	1.354 (7)	C15—H15	0.9300
C7—C8	1.370 (7)	C16—H16	0.9300
C8—C9	1.371 (7)	C17—H17	0.9300
C9—C10	1.391 (6)	C18—H18	0.9300
C9—C12	1.490 (7)	C19—H19	0.9300
C10—C11	1.380 (8)

Cl1—Cu1—O1	110.53 (10)	C14—C13—C18	116.7 (4)
Cl1—Cu1—N1	110.94 (11)	C13—C14—C15	119.1 (4)
Cl1—Cu1—N3	94.50 (9)	C13—C14—C19	124.3 (4)
Cl1—Cu1—N4	111.53 (11)	C15—C14—C19	116.5 (4)
O1—Cu1—N1	100.91 (14)	C14—C15—C16	121.7 (5)
O1—Cu1—N3	144.00 (12)	C15—C16—C17	119.5 (5)
O1—Cu1—N4	94.01 (14)	C16—C17—C18	120.6 (5)
N1—Cu1—N3	93.31 (13)	C13—C18—C17	122.4 (5)
N1—Cu1—N4	125.93 (15)	N4—C19—C14	127.5 (4)
N3—Cu1—N4	51.74 (13)	C1—C2—H2	120.00
Cu1—O1—C13	126.7 (3)	C3—C2—H2	120.00
Cu1—N1—C1	125.6 (3)	C3—C4—H4	121.00
Cu1—N1—C5	117.3 (3)	C5—C4—H4	120.00
C1—N1—C5	117.1 (4)	N1—C5—H5	118.00
Cu1—N3—C7	78.6 (3)	C4—C5—H5	118.00
Cu1—N3—C11	162.7 (3)	C3—C6—H6A	109.00
C7—N3—C11	116.7 (4)	C3—C6—H6B	109.00
Cu1—N4—C7	116.5 (3)	C3—C6—H6C	109.00
Cu1—N4—C19	122.9 (3)	H6A—C6—H6B	109.00
C7—N4—C19	120.6 (4)	H6A—C6—H6C	109.00
H2NA—N2—H2NB	124 (5)	H6B—C6—H6C	109.00
C1—N2—H2NB	114 (3)	C7—C8—H8	120.00
C1—N2—H2NA	119 (3)	C9—C8—H8	120.00
N2—C1—C2	121.0 (4)	C9—C10—H10	121.00
N1—C1—N2	118.1 (4)	C11—C10—H10	121.00
N1—C1—C2	120.9 (5)	N3—C11—H11	118.00
C1—C2—C3	120.5 (4)	C10—C11—H11	118.00
C2—C3—C4	118.4 (4)	C9—C12—H12A	109.00
C2—C3—C6	121.2 (4)	C9—C12—H12B	109.00
C4—C3—C6	120.4 (5)	C9—C12—H12C	109.00
C3—C4—C5	119.0 (5)	H12A—C12—H12B	110.00
N1—C5—C4	124.2 (4)	H12A—C12—H12C	110.00
N3—C7—C8	123.6 (5)	H12B—C12—H12C	109.00
N3—C7—N4	111.1 (4)	C14—C15—H15	119.00
N4—C7—C8	125.2 (4)	C16—C15—H15	119.00
C7—C8—C9	119.8 (4)	C15—C16—H16	120.00
C8—C9—C10	117.0 (4)	C17—C16—H16	120.00
C10—C9—C12	121.2 (5)	C16—C17—H17	120.00
C8—C9—C12	121.8 (4)	C18—C17—H17	120.00
C9—C10—C11	118.7 (5)	C13—C18—H18	119.00
N3—C11—C10	124.0 (5)	C17—C18—H18	119.00
O1—C13—C14	124.4 (4)	N4—C19—H19	116.00
O1—C13—C18	118.8 (4)	C14—C19—H19	116.00

Cl1—Cu1—O1—C13	−113.3 (4)	C11—N3—C7—C8	3.8 (8)
N1—Cu1—O1—C13	129.3 (4)	C7—N3—C11—C10	−2.4 (9)
N3—Cu1—O1—C13	17.9 (5)	Cu1—N4—C7—N3	−17.2 (5)
N4—Cu1—O1—C13	1.5 (4)	Cu1—N4—C7—C8	161.1 (4)
Cl1—Cu1—N1—C1	52.5 (4)	C19—N4—C7—N3	162.7 (4)
Cl1—Cu1—N1—C5	−123.3 (3)	C19—N4—C7—C8	−19.0 (7)
O1—Cu1—N1—C1	169.6 (4)	Cu1—N4—C19—C14	1.3 (7)
O1—Cu1—N1—C5	−6.1 (3)	C7—N4—C19—C14	−178.6 (5)
N3—Cu1—N1—C1	−43.6 (4)	N1—C1—C2—C3	−1.3 (7)
N3—Cu1—N1—C5	140.6 (3)	N2—C1—C2—C3	−179.5 (5)
N4—Cu1—N1—C1	−87.2 (4)	C1—C2—C3—C4	−0.8 (7)
N4—Cu1—N1—C5	97.0 (4)	C1—C2—C3—C6	179.6 (4)
Cl1—Cu1—N3—C7	104.9 (3)	C2—C3—C4—C5	1.8 (7)
O1—Cu1—N3—C7	−30.1 (4)	C6—C3—C4—C5	−178.6 (4)
N1—Cu1—N3—C7	−143.8 (3)	C3—C4—C5—N1	−0.7 (7)
N4—Cu1—N3—C7	−9.1 (3)	N3—C7—C8—C9	−2.2 (8)
Cl1—Cu1—N4—C7	−68.9 (3)	N4—C7—C8—C9	179.8 (5)
Cl1—Cu1—N4—C19	111.2 (4)	C7—C8—C9—C10	−1.1 (7)
O1—Cu1—N4—C7	177.2 (3)	C7—C8—C9—C12	177.9 (5)
O1—Cu1—N4—C19	−2.7 (4)	C8—C9—C10—C11	2.4 (8)
N1—Cu1—N4—C7	70.6 (4)	C12—C9—C10—C11	−176.6 (5)
N1—Cu1—N4—C19	−109.3 (4)	C9—C10—C11—N3	−0.7 (9)
N3—Cu1—N4—C7	9.4 (3)	O1—C13—C14—C15	178.6 (5)
N3—Cu1—N4—C19	−170.5 (4)	O1—C13—C14—C19	−3.8 (8)
Cu1—O1—C13—C14	1.3 (7)	C18—C13—C14—C15	−0.3 (7)
Cu1—O1—C13—C18	−179.9 (3)	C18—C13—C14—C19	177.3 (5)
Cu1—N1—C1—N2	4.9 (6)	O1—C13—C18—C17	−179.9 (5)
Cu1—N1—C1—C2	−173.4 (3)	C14—C13—C18—C17	−1.0 (8)
C5—N1—C1—N2	−179.4 (5)	C13—C14—C15—C16	0.6 (8)
C5—N1—C1—C2	2.4 (6)	C19—C14—C15—C16	−177.2 (5)
Cu1—N1—C5—C4	174.7 (4)	C13—C14—C19—N4	2.4 (9)
C1—N1—C5—C4	−1.4 (7)	C15—C14—C19—N4	−179.9 (5)
Cu1—N3—C7—N4	10.8 (3)	C14—C15—C16—C17	0.3 (9)
Cu1—N3—C7—C8	−167.5 (5)	C15—C16—C17—C18	−1.6 (9)
C11—N3—C7—N4	−177.9 (5)	C16—C17—C18—C13	2.0 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2NB···N3	0.85 (4)	2.27 (4)	3.039 (6)	150 (5)
N2—H2NA···Cl1ⁱ	0.86 (4)	2.44 (4)	3.305 (5)	179 (7)

Symmetry code: (i) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	[Cu(C₁₃H₁₁N₂O)Cl(C₆H₈N₂)]
M_r	418.37
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	300
a, b, c (Å)	17.443 (4), 11.2197 (19), 9.4435 (19)
β (°)	92.67 (2)
V (Å³)	1846.1 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.34
Crystal size (mm)	0.4 × 0.4 × 0.06

Data collection
Diffractometer	Oxford Diffraction Xcalibur, Eos diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.565, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7213, 3339, 2017
R_int	0.063
(sin θ/λ)_max (Å⁻¹)	0.600

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.114, 0.94
No. of reflections	3339
No. of parameters	243
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.45

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009) and PLATON (Spek, 2009), OLEX2 (Dolomanov et al., 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2NB···N3	0.85 (4)	2.27 (4)	3.039 (6)	150 (5)
N2—H2NA···Cl1ⁱ	0.86 (4)	2.44 (4)	3.305 (5)	179 (7)

Symmetry code: (i) x, −y+1/2, z−1/2.

Footnotes

‡Deceased.

Acknowledgements

BB thanks the Department of Science and Technolgy, New Delhi, India, for financial support and for providing the single-crystal X-ray diffractometer facility at the Department of Chemistry, Pondicherry University, under the DST–FIST program.

References

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