(Dimethyl-formamide-κO)[2-meth-oxy-6-(2-pyridylmethyl-imino-meth-yl)phenolato-κN,N',O](thio-cyanato-κN)copper(II).

In the title compound, [Cu(C(14)H(13)N(2)O(2))(NCS)(C(3)H(7)NO)], the Cu(2+) ion is coordinated by an N,N',O-tridentate 2-meth-oxy-6-(2-pyridylmethyl-imino-meth-yl)phenolate ligand, an N-bonded thio-cyanate ion and an O-bonded dimethyl-formamide (DMF) mol-ecule, resulting in a distorted CuN(3)O(2) square-based pyramidal geometry for the metal ion, with the DMF O atom in the apical site. The dihedral angle between the aromatic rings in the ligand is 8.70 (16)°. The S atom is disordered over two positions in a 0.901 (6):0.099 (6) ratio. In the crystal, mol-ecules inter-act by way of π-π stacking inter-actions [centroid-centroid separation = 3.720 (2) Å].

Related literature

For the synthesis, see: Pointeau et al. (1986 ▶). For related structures, see: Li & Zhang (2004 ▶); You & Zhu (2004 ▶).

Experimental

Crystal data

[Cu(C14H13N2O2)(NCS)(C3H7NO)]

M = 435.98

Triclinic,

a = 8.6768 (9) Å

b = 10.9310 (11) Å

c = 11.0689 (12) Å

α = 83.251 (2)°

β = 72.023 (1)°

γ = 79.530 (1)°

V = 979.84 (18) Å3

Z = 2

Mo Kα radiation

μ = 1.25 mm−1

T = 298 K

0.20 × 0.12 × 0.09 mm

Data collection

Rigaku SCXmini diffractometer

Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ▶) T min = 0.737, T max = 0.868

5129 measured reflections

3392 independent reflections

2679 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.090

S = 1.09

3392 reflections

251 parameters

H-atom parameters constrained

Δρmax = 0.33 e Å−3

Δρmin = −0.37 e Å−3

Data collection: CrystalClear (Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810014212/hb5406sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014212/hb5406Isup2.hkl

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

[Cu(C14H13N2O2)(NCS)(C3H7NO)]	Z = 2
Mr = 435.98	F(000) = 450
Triclinic, P1	Dx = 1.478 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6768 (9) Å	Cell parameters from 13380 reflections
b = 10.9310 (11) Å	θ = 3.0–27.6°
c = 11.0689 (12) Å	µ = 1.25 mm−1
α = 83.251 (2)°	T = 298 K
β = 72.023 (1)°	Prism, dark brown
γ = 79.530 (1)°	0.20 × 0.12 × 0.09 mm
V = 979.84 (18) Å3

Rigaku SCXmini diffractometer	3392 independent reflections
Radiation source: fine-focus sealed tube	2679 reflections with I > 2σ(I)
graphite	Rint = 0.016
Detector resolution: 8.192 pixels mm-1	θmax = 25.0°, θmin = 1.9°
Thin–slice ω scans	h = −9→10
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −13→7
Tmin = 0.737, Tmax = 0.868	l = −12→13
5129 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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.090	H-atom parameters constrained
S = 1.09	w = 1/[σ2(Fo2) + (0.039P)2 + 0.2715P] where P = (Fo2 + 2Fc2)/3
3392 reflections	(Δ/σ)max = 0.001
251 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.37 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 > 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	Occ. (<1)
Cu1	0.63382 (4)	0.88140 (3)	0.58156 (3)	0.03823 (14)
S1	0.1914 (3)	0.73555 (19)	0.89276 (15)	0.0641 (6)	0.901 (6)
S1'	0.255 (2)	0.6960 (16)	0.9198 (14)	0.0641 (6)	0.099 (6)
N1	0.7507 (3)	0.9830 (2)	0.4385 (2)	0.0367 (5)
N2	0.6888 (3)	1.0010 (2)	0.6814 (2)	0.0386 (6)
N3	0.4812 (3)	0.8079 (2)	0.7321 (2)	0.0450 (6)
N4	0.9692 (3)	0.5684 (2)	0.7084 (3)	0.0512 (7)
O1	0.5788 (2)	0.78300 (18)	0.47433 (19)	0.0442 (5)
O2	0.4899 (3)	0.61550 (19)	0.3729 (2)	0.0514 (6)
O3	0.8691 (3)	0.73557 (19)	0.5981 (2)	0.0545 (6)
C1	0.7883 (3)	0.9606 (3)	0.3205 (3)	0.0405 (7)
H1	0.8535	1.0123	0.2618	0.049*
C2	0.7394 (3)	0.8639 (3)	0.2710 (3)	0.0385 (7)
C3	0.6353 (3)	0.7818 (3)	0.3508 (3)	0.0385 (7)
C4	0.5880 (4)	0.6919 (3)	0.2902 (3)	0.0430 (7)
C5	0.6418 (4)	0.6871 (3)	0.1600 (3)	0.0514 (8)
H5	0.6084	0.6291	0.1223	0.062*
C6	0.7457 (4)	0.7678 (3)	0.0834 (3)	0.0575 (9)
H6	0.7818	0.7628	−0.0044	0.069*
C7	0.7939 (4)	0.8537 (3)	0.1377 (3)	0.0507 (8)
H7	0.8639	0.9066	0.0863	0.061*
C8	0.4532 (5)	0.5136 (3)	0.3227 (4)	0.0697 (11)
H8A	0.3792	0.5445	0.2732	0.105*
H8B	0.4032	0.4579	0.3914	0.105*
H8C	0.5526	0.4698	0.2696	0.105*
C9	0.8024 (4)	1.0923 (3)	0.4699 (3)	0.0417 (7)
H9A	0.7397	1.1677	0.4433	0.050*
H9B	0.9175	1.0936	0.4252	0.050*
C10	0.7757 (3)	1.0878 (3)	0.6111 (3)	0.0388 (7)
C11	0.8352 (4)	1.1694 (3)	0.6660 (3)	0.0479 (8)
H11	0.8973	1.2277	0.6155	0.058*
C12	0.8012 (4)	1.1628 (3)	0.7959 (3)	0.0525 (8)
H12	0.8393	1.2173	0.8345	0.063*
C13	0.7099 (4)	1.0746 (3)	0.8691 (3)	0.0550 (9)
H13	0.6850	1.0692	0.9573	0.066*
C14	0.6569 (4)	0.9956 (3)	0.8089 (3)	0.0496 (8)
H14	0.5964	0.9356	0.8579	0.059*
C15	0.3643 (4)	0.7751 (3)	0.7999 (3)	0.0399 (7)
C16	0.8581 (4)	0.6634 (3)	0.6928 (3)	0.0490 (8)
H16	0.7623	0.6769	0.7599	0.059*
C17	0.9490 (5)	0.4915 (4)	0.8262 (4)	0.0790 (12)
H17A	1.0281	0.5039	0.8662	0.118*
H17B	0.9649	0.4055	0.8087	0.118*
H17C	0.8405	0.5142	0.8820	0.118*
C18	1.1236 (5)	0.5440 (4)	0.6098 (4)	0.0901 (14)
H18A	1.1135	0.5866	0.5310	0.135*
H18B	1.1522	0.4559	0.5996	0.135*
H18C	1.2077	0.5731	0.6333	0.135*

	U11	U22	U33	U12	U13	U23
Cu1	0.0348 (2)	0.0348 (2)	0.0399 (2)	−0.00972 (15)	−0.00338 (15)	0.00433 (15)
S1	0.0534 (10)	0.0732 (10)	0.0568 (7)	−0.0317 (8)	0.0074 (7)	0.0010 (6)
S1'	0.0534 (10)	0.0732 (10)	0.0568 (7)	−0.0317 (8)	0.0074 (7)	0.0010 (6)
N1	0.0332 (13)	0.0317 (13)	0.0418 (15)	−0.0070 (10)	−0.0076 (11)	0.0055 (10)
N2	0.0333 (13)	0.0359 (14)	0.0412 (15)	−0.0073 (10)	−0.0041 (11)	0.0034 (11)
N3	0.0414 (14)	0.0411 (15)	0.0473 (16)	−0.0123 (12)	−0.0039 (13)	0.0023 (12)
N4	0.0492 (16)	0.0414 (16)	0.0636 (18)	−0.0062 (13)	−0.0228 (14)	0.0096 (13)
O1	0.0451 (12)	0.0429 (12)	0.0410 (13)	−0.0173 (9)	−0.0029 (10)	0.0004 (9)
O2	0.0515 (13)	0.0434 (13)	0.0574 (14)	−0.0159 (10)	−0.0072 (11)	−0.0065 (10)
O3	0.0445 (13)	0.0485 (14)	0.0601 (15)	0.0008 (10)	−0.0118 (11)	0.0156 (11)
C1	0.0311 (15)	0.0377 (17)	0.0450 (19)	−0.0043 (13)	−0.0058 (13)	0.0120 (13)
C2	0.0321 (15)	0.0351 (16)	0.0425 (18)	−0.0011 (12)	−0.0070 (13)	0.0034 (13)
C3	0.0310 (15)	0.0325 (16)	0.0461 (19)	0.0040 (12)	−0.0092 (13)	0.0006 (13)
C4	0.0359 (16)	0.0380 (17)	0.052 (2)	−0.0006 (13)	−0.0120 (14)	−0.0023 (14)
C5	0.052 (2)	0.050 (2)	0.054 (2)	−0.0060 (16)	−0.0167 (17)	−0.0080 (16)
C6	0.065 (2)	0.063 (2)	0.0405 (19)	−0.0064 (18)	−0.0121 (17)	−0.0028 (16)
C7	0.0478 (19)	0.054 (2)	0.0447 (19)	−0.0083 (15)	−0.0085 (15)	0.0073 (15)
C8	0.071 (2)	0.055 (2)	0.084 (3)	−0.0228 (19)	−0.012 (2)	−0.021 (2)
C9	0.0393 (16)	0.0373 (17)	0.0471 (19)	−0.0141 (13)	−0.0109 (14)	0.0100 (13)
C10	0.0282 (14)	0.0326 (16)	0.0502 (19)	−0.0010 (12)	−0.0074 (13)	0.0014 (13)
C11	0.0413 (17)	0.0449 (19)	0.056 (2)	−0.0119 (14)	−0.0129 (15)	0.0064 (15)
C12	0.052 (2)	0.050 (2)	0.060 (2)	−0.0109 (16)	−0.0202 (17)	−0.0063 (16)
C13	0.059 (2)	0.058 (2)	0.046 (2)	−0.0076 (17)	−0.0131 (17)	−0.0038 (16)
C14	0.0510 (19)	0.0473 (19)	0.047 (2)	−0.0154 (15)	−0.0074 (16)	0.0042 (15)
C15	0.0478 (18)	0.0331 (16)	0.0367 (17)	−0.0109 (14)	−0.0066 (15)	−0.0022 (13)
C16	0.0421 (18)	0.0425 (19)	0.059 (2)	−0.0060 (15)	−0.0104 (16)	−0.0016 (16)
C17	0.090 (3)	0.068 (3)	0.080 (3)	−0.016 (2)	−0.039 (2)	0.032 (2)
C18	0.061 (2)	0.090 (3)	0.092 (3)	0.024 (2)	−0.012 (2)	0.016 (2)

Cu1—O1	1.905 (2)	C5—H5	0.9300
Cu1—N1	1.942 (2)	C6—C7	1.358 (5)
Cu1—N3	1.971 (3)	C6—H6	0.9300
Cu1—N2	2.012 (2)	C7—H7	0.9300
Cu1—O3	2.392 (2)	C8—H8A	0.9600
S1—C15	1.635 (3)	C8—H8B	0.9600
S1'—C15	1.633 (13)	C8—H8C	0.9600
N1—C1	1.287 (4)	C9—C10	1.504 (4)
N1—C9	1.463 (3)	C9—H9A	0.9700
N2—C10	1.342 (4)	C9—H9B	0.9700
N2—C14	1.347 (4)	C10—C11	1.385 (4)
N3—C15	1.149 (4)	C11—C12	1.372 (4)
N4—C16	1.317 (4)	C11—H11	0.9300
N4—C18	1.447 (5)	C12—C13	1.383 (4)
N4—C17	1.447 (4)	C12—H12	0.9300
O1—C3	1.304 (3)	C13—C14	1.368 (4)
O2—C4	1.364 (4)	C13—H13	0.9300
O2—C8	1.426 (4)	C14—H14	0.9300
O3—C16	1.225 (4)	C16—H16	0.9300
C1—C2	1.427 (4)	C17—H17A	0.9600
C1—H1	0.9300	C17—H17B	0.9600
C2—C7	1.416 (4)	C17—H17C	0.9600
C2—C3	1.420 (4)	C18—H18A	0.9600
C3—C4	1.433 (4)	C18—H18B	0.9600
C4—C5	1.375 (4)	C18—H18C	0.9600
C5—C6	1.397 (5)
O1—Cu1—N1	92.88 (9)	O2—C8—H8B	109.5
O1—Cu1—N3	90.19 (9)	H8A—C8—H8B	109.5
N1—Cu1—N3	168.56 (9)	O2—C8—H8C	109.5
O1—Cu1—N2	173.84 (9)	H8A—C8—H8C	109.5
N1—Cu1—N2	82.13 (10)	H8B—C8—H8C	109.5
N3—Cu1—N2	94.01 (10)	N1—C9—C10	109.5 (2)
O1—Cu1—O3	93.96 (8)	N1—C9—H9A	109.8
N1—Cu1—O3	96.07 (8)	C10—C9—H9A	109.8
N3—Cu1—O3	94.71 (9)	N1—C9—H9B	109.8
N2—Cu1—O3	90.18 (8)	C10—C9—H9B	109.8
C1—N1—C9	118.2 (2)	H9A—C9—H9B	108.2
C1—N1—Cu1	125.6 (2)	N2—C10—C11	121.8 (3)
C9—N1—Cu1	116.20 (18)	N2—C10—C9	116.1 (3)
C10—N2—C14	118.4 (3)	C11—C10—C9	122.2 (3)
C10—N2—Cu1	115.2 (2)	C12—C11—C10	119.0 (3)
C14—N2—Cu1	126.2 (2)	C12—C11—H11	120.5
C15—N3—Cu1	161.4 (3)	C10—C11—H11	120.5
C16—N4—C18	120.1 (3)	C11—C12—C13	119.5 (3)
C16—N4—C17	122.3 (3)	C11—C12—H12	120.2
C18—N4—C17	117.5 (3)	C13—C12—H12	120.2
C3—O1—Cu1	127.30 (19)	C14—C13—C12	118.5 (3)
C4—O2—C8	117.7 (3)	C14—C13—H13	120.7
C16—O3—Cu1	119.2 (2)	C12—C13—H13	120.7
N1—C1—C2	126.2 (3)	N2—C14—C13	122.7 (3)
N1—C1—H1	116.9	N2—C14—H14	118.6
C2—C1—H1	116.9	C13—C14—H14	118.6
C7—C2—C3	119.9 (3)	N3—C15—S1'	156.9 (9)
C7—C2—C1	118.0 (3)	N3—C15—S1	176.5 (3)
C3—C2—C1	122.1 (3)	S1'—C15—S1	26.5 (8)
O1—C3—C2	124.9 (3)	O3—C16—N4	126.1 (3)
O1—C3—C4	117.8 (3)	O3—C16—H16	116.9
C2—C3—C4	117.3 (3)	N4—C16—H16	116.9
O2—C4—C5	125.5 (3)	N4—C17—H17A	109.5
O2—C4—C3	113.9 (3)	N4—C17—H17B	109.5
C5—C4—C3	120.6 (3)	H17A—C17—H17B	109.5
C4—C5—C6	121.2 (3)	N4—C17—H17C	109.5
C4—C5—H5	119.4	H17A—C17—H17C	109.5
C6—C5—H5	119.4	H17B—C17—H17C	109.5
C7—C6—C5	119.8 (3)	N4—C18—H18A	109.5
C7—C6—H6	120.1	N4—C18—H18B	109.5
C5—C6—H6	120.1	H18A—C18—H18B	109.5
C6—C7—C2	121.2 (3)	N4—C18—H18C	109.5
C6—C7—H7	119.4	H18A—C18—H18C	109.5
C2—C7—H7	119.4	H18B—C18—H18C	109.5
O2—C8—H8A	109.5

Cu1—O1	1.905 (2)
Cu1—N1	1.942 (2)
Cu1—N3	1.971 (3)
Cu1—N2	2.012 (2)
Cu1—O3	2.392 (2)

O1—Cu1—N1	92.88 (9)
O1—Cu1—N3	90.19 (9)
N1—Cu1—N3	168.56 (9)
O1—Cu1—N2	173.84 (9)
N1—Cu1—N2	82.13 (10)
N3—Cu1—N2	94.01 (10)
O1—Cu1—O3	93.96 (8)
N1—Cu1—O3	96.07 (8)
N3—Cu1—O3	94.71 (9)
N2—Cu1—O3	90.18 (8)