Crystal structure of di-chlorido-bis-(methyl isonicotinate-κN)copper(II).

In the title compound, [CuCl2(C7H7NO2)2], the square-planar-coordinated Cu(II) ion lies on a centre of symmetry and is bonded to two monodentate methyl-isonicotinate ligands through their N atoms and by two chloride ligands. The mol-ecules pack in a herringbone pattern. Perpendicular to [100] there are weak inter-molecular C-H⋯Cl and C-H⋯O contacts. Along [100] there are infinite chains of edge-sharing octa-hedra linked through the chlorido ligands.

Related literature

For related structures, see: Vitorica-Yrezabal et al. (2011 ▸); Laing & Carr (1971 ▸); Chen & Mak (2006 ▸); Ge et al. (2006 ▸); Chen et al. (2011 ▸); Ma et al. (2010 ▸). For background to isonicotinate, see: Zhou et al. (2006 ▸); Bera et al. (2001 ▸); Cotton et al. (2007 ▸); Tella et al. (2014 ▸). For the synthesis of 4-(5-phenyl-1,3,4-oxa­diazol-2-yl)pyridine, used in the preparation, see: Kangani & Day (2009 ▸).

Experimental

Crystal data

[CuCl2(C7H7NO2)2]

M = 408.71

Monoclinic,

a = 3.7792 (4) Å

b = 29.891 (4) Å

c = 7.0139 (8) Å

β = 94.036 (10)°

V = 790.36 (16) Å3

Z = 2

Mo Kα radiation

μ = 1.74 mm−1

T = 173 K

0.50 × 0.05 × 0.04 mm

Data collection

Oxford Diffraction Xcalibur 3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2011 ▸) T min = 0.775, T max = 1.000

4265 measured reflections

1617 independent reflections

1404 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.091

S = 1.09

1617 reflections

107 parameters

H-atom parameters constrained

Δρmax = 0.53 e Å−3

Δρmin = −0.69 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2011 ▸); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▸); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2008 ▸, 2015 ▸); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ▸); software used to prepare material for publication: PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S205698901500729X/cq2014sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S205698901500729X/cq2014Isup2.hkl

Click here for additional data file.

x y z . DOI: 10.1107/S205698901500729X/cq2014fig1.tif

The mol­ecular structure of the title compound (ellipsoids drawn at the 30% probability level). Symmetry code: i = 1 − x, −y, 1 − z. Non-labelled non-hydrogen atoms have been generated by symmetry i.

Click here for additional data file.

. DOI: 10.1107/S205698901500729X/cq2014fig2.tif

The unit cell viewed along [100] (ellipsoids drawn at the 50% probability level). Inter­molecular C—H⋯Cl and C—H⋯O contacts are indicated by dashed lines.

Click here for additional data file.

. DOI: 10.1107/S205698901500729X/cq2014fig3.tif

Infinite strands along [100] formed by inter­molecular Cu—Cl bonds (thin bond diameter) (drawn at the 30% ellipsoid probability level).

CCDC reference: 1059032

Additional supporting information: crystallographic information; 3D view; checkCIF report

[CuCl2(C7H7NO2)2]	F(000) = 414
Mr = 408.71	Dx = 1.717 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
a = 3.7792 (4) Å	Cell parameters from 1293 reflections
b = 29.891 (4) Å	θ = 4.5–26.3°
c = 7.0139 (8) Å	µ = 1.74 mm−1
β = 94.036 (10)°	T = 173 K
V = 790.36 (16) Å3	Rod, green
Z = 2	0.50 × 0.05 × 0.04 mm

Oxford Diffraction Xcalibur 3 diffractometer	1617 independent reflections
Radiation source: fine-focus sealed tube	1404 reflections with I > 2σ(I)
Detector resolution: 15.9809 pixels mm-1	Rint = 0.034
ω scans	θmax = 26.4°, θmin = 4.5°
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2011)	h = −4→4
Tmin = 0.775, Tmax = 1.000	k = −33→37
4265 measured reflections	l = −8→6

Refinement on F2	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036	H-atom parameters constrained
wR(F2) = 0.091	w = 1/[σ2(Fo2) + (0.0388P)2 + 0.6044P] where P = (Fo2 + 2Fc2)/3
S = 1.09	(Δ/σ)max < 0.001
1617 reflections	Δρmax = 0.53 e Å−3
107 parameters	Δρmin = −0.69 e Å−3

Experimental. Absorption correction: CrysAlisPro (Oxford Diffraction, 2011) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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.

	x	y	z	Uiso*/Ueq
Cu1	0.5000	0.0000	0.5000	0.01825 (17)
Cl1	0.91406 (17)	0.03090 (2)	0.71647 (9)	0.01768 (18)
O2	0.3701 (7)	0.17679 (8)	−0.1593 (3)	0.0414 (7)
O1	0.1672 (6)	0.20909 (6)	0.0994 (3)	0.0291 (5)
N1	0.4707 (6)	0.05771 (7)	0.3486 (3)	0.0168 (5)
C1	0.5365 (7)	0.05831 (9)	0.1633 (4)	0.0180 (6)
H1	0.6172	0.0316	0.1070	0.022*
C2	0.4918 (7)	0.09617 (9)	0.0505 (4)	0.0197 (6)
H2	0.5444	0.0955	−0.0800	0.024*
C3	0.3693 (7)	0.13491 (9)	0.1308 (4)	0.0174 (6)
C4	0.3076 (8)	0.13494 (9)	0.3240 (4)	0.0188 (6)
H4	0.2278	0.1613	0.3837	0.023*
C5	0.3647 (8)	0.09584 (9)	0.4276 (4)	0.0202 (6)
H5	0.3272	0.0961	0.5601	0.024*
C6	0.3063 (8)	0.17503 (10)	0.0051 (4)	0.0236 (7)
C7	0.0886 (11)	0.24908 (11)	−0.0132 (5)	0.0384 (9)
H7A	0.3090	0.2613	−0.0577	0.058*
H7B	−0.0224	0.2714	0.0657	0.058*
H7C	−0.0739	0.2416	−0.1236	0.058*

	U11	U22	U33	U12	U13	U23
Cu1	0.0235 (3)	0.0123 (3)	0.0184 (3)	−0.00169 (19)	−0.0021 (2)	0.00175 (18)
Cl1	0.0186 (3)	0.0170 (4)	0.0175 (3)	−0.0002 (3)	0.0016 (3)	−0.0023 (2)
O2	0.0712 (19)	0.0277 (13)	0.0274 (13)	0.0115 (12)	0.0191 (13)	0.0092 (10)
O1	0.0465 (14)	0.0169 (11)	0.0239 (12)	0.0100 (10)	0.0035 (10)	0.0022 (9)
N1	0.0175 (12)	0.0144 (12)	0.0185 (12)	0.0009 (9)	0.0002 (9)	−0.0003 (9)
C1	0.0201 (14)	0.0150 (14)	0.0192 (14)	0.0007 (11)	0.0038 (11)	−0.0031 (11)
C2	0.0220 (15)	0.0190 (15)	0.0185 (14)	−0.0010 (11)	0.0048 (11)	−0.0006 (11)
C3	0.0169 (14)	0.0141 (14)	0.0210 (14)	−0.0016 (10)	0.0003 (11)	0.0010 (11)
C4	0.0212 (14)	0.0146 (14)	0.0211 (15)	0.0005 (11)	0.0043 (11)	−0.0029 (11)
C5	0.0242 (15)	0.0186 (14)	0.0184 (14)	−0.0006 (12)	0.0049 (12)	−0.0007 (11)
C6	0.0254 (16)	0.0192 (16)	0.0264 (17)	0.0002 (12)	0.0023 (13)	0.0000 (12)
C7	0.056 (2)	0.0217 (17)	0.037 (2)	0.0133 (16)	0.0034 (17)	0.0075 (14)

Cu1—N1	2.025 (2)	C1—H1	0.9500
Cu1—N1i	2.025 (2)	C2—C3	1.382 (4)
Cu1—Cl1	2.2962 (7)	C2—H2	0.9500
Cu1—Cl1i	2.2962 (7)	C3—C4	1.391 (4)
Cu1—Cl1ii	2.9215 (7)	C3—C6	1.498 (4)
Cu1—Cl1iii	2.9215 (7)	C4—C5	1.385 (4)
O2—C6	1.196 (4)	C4—H4	0.9500
O1—C6	1.341 (3)	C5—H5	0.9500
O1—C7	1.452 (4)	C7—H7A	0.9800
N1—C1	1.340 (4)	C7—H7B	0.9800
N1—C5	1.341 (3)	C7—H7C	0.9800
C1—C2	1.385 (4)
N1—Cu1—N1i	180.00 (6)	C3—C2—C1	118.9 (3)
N1—Cu1—Cl1	90.79 (7)	C3—C2—H2	120.6
N1i—Cu1—Cl1	89.21 (7)	C1—C2—H2	120.6
N1—Cu1—Cl1i	89.21 (7)	C2—C3—C4	118.8 (3)
N1i—Cu1—Cl1i	90.79 (7)	C2—C3—C6	118.4 (3)
Cl1—Cu1—Cl1i	180.0	C4—C3—C6	122.8 (3)
N1—Cu1—Cl1ii	90.70 (7)	C5—C4—C3	118.7 (3)
N1i—Cu1—Cl1ii	89.29 (7)	C5—C4—H4	120.7
Cl1—Cu1—Cl1ii	87.97 (2)	C3—C4—H4	120.7
Cl1i—Cu1—Cl1ii	92.03 (2)	N1—C5—C4	122.7 (3)
N1—Cu1—Cl1iii	89.30 (7)	N1—C5—H5	118.6
N1i—Cu1—Cl1iii	90.71 (7)	C4—C5—H5	118.6
Cl1—Cu1—Cl1iii	92.03 (2)	O2—C6—O1	123.7 (3)
Cl1i—Cu1—Cl1iii	87.97 (2)	O2—C6—C3	124.6 (3)
Cl1ii—Cu1—Cl1iii	180.0	O1—C6—C3	111.7 (2)
C6—O1—C7	115.4 (2)	O1—C7—H7A	109.5
C1—N1—C5	118.1 (2)	O1—C7—H7B	109.5
C1—N1—Cu1	120.86 (18)	H7A—C7—H7B	109.5
C5—N1—Cu1	120.97 (19)	O1—C7—H7C	109.5
N1—C1—C2	122.8 (3)	H7A—C7—H7C	109.5
N1—C1—H1	118.6	H7B—C7—H7C	109.5
C2—C1—H1	118.6
C5—N1—C1—C2	−1.5 (4)	Cu1—N1—C5—C4	−173.5 (2)
Cu1—N1—C1—C2	174.6 (2)	C3—C4—C5—N1	−1.3 (4)
N1—C1—C2—C3	−1.0 (4)	C7—O1—C6—O2	1.3 (5)
C1—C2—C3—C4	2.3 (4)	C7—O1—C6—C3	−178.5 (3)
C1—C2—C3—C6	−177.2 (3)	C2—C3—C6—O2	−3.7 (5)
C2—C3—C4—C5	−1.2 (4)	C4—C3—C6—O2	176.8 (3)
C6—C3—C4—C5	178.3 (3)	C2—C3—C6—O1	176.1 (3)
C1—N1—C5—C4	2.7 (4)	C4—C3—C6—O1	−3.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···Cl1iv	0.95	2.83	3.517 (3)	130
C7—H7B···O2v	0.98	2.53	3.470 (4)	161
C7—H7C···O1vi	0.98	2.58	3.298 (4)	130

Table 1

Hydrogen-bond geometry (, )

DHA	DH	HA	D A	DHA
C2H2Cl1i	0.95	2.83	3.517(3)	130
C7H7BO2ii	0.98	2.53	3.470(4)	161
C7H7CO1iii	0.98	2.58	3.298(4)	130

Symmetry codes: (i) ; (ii) ; (iii) .