{2,4-Dibromo-6-[(2-dimethyl­amino­ethyl­imino)meth­yl]phenolato}(thio­cyanato)copper(II)

In the mononuclear copper(II) title compound, [Cu(C₁₁H₁₃Br₂N₂O)(NCS)], the Cu^II atom is four-coordinated by one imine N, one amine N, and one phenolate O atom of the Schiff base ligand, and by one N atom of a thio­cyanate anion in a square planar geometry. In the crystal structure, adjacent mol­ecules are linked through inter­molecular C—H...Br hydrogen bonds, forming centrosymmetric dimers.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.044
• wR factor = 0.105
• Data-to-parameter ratio = 17.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.99
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.67 Ratio
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         N3
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C9
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N2
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C12
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.

{2,4-Dibromo-6-[(2-dimethylaminoethylimino)methyl]phenolato}(thiocyanato) copper(II)

Crystal data

[Cu(C11H13Br2N2O)(NCS)]	F(000) = 916
Mr = 470.67	Dx = 2.028 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1683 reflections
a = 7.146 (1) Å	θ = 2.5–24.9°
b = 19.213 (3) Å	µ = 6.73 mm^−1
c = 11.229 (2) Å	T = 298 K
β = 91.026 (2)°	Needle, red
V = 1541.5 (4) Å^3	0.42 × 0.08 × 0.04 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer	3180 independent reflections
Radiation source: fine-focus sealed tube	2014 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.067
ω scans	θmax = 26.5°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.164, Tmax = 0.775	k = −24→23
12315 measured reflections	l = −14→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.105	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0345P)^2 + 0.8169P] where P = (Fo^2 + 2Fc^2)/3
3180 reflections	(Δ/σ)max < 0.001
183 parameters	Δρmax = 0.60 e Å^−3
0 restraints	Δρmin = −0.52 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cu1	0.81387 (9)	0.17688 (3)	0.15230 (6)	0.0392 (2)
Br1	0.84037 (11)	0.11739 (3)	−0.26990 (5)	0.0654 (2)
Br2	0.68442 (10)	−0.16013 (3)	−0.15619 (6)	0.0583 (2)
S1	0.8370 (3)	0.41037 (8)	0.03827 (16)	0.0627 (5)
O1	0.8142 (5)	0.13639 (18)	−0.0028 (3)	0.0438 (9)
N1	0.7943 (6)	0.0872 (2)	0.2289 (4)	0.0390 (11)
N2	0.8354 (7)	0.2145 (2)	0.3233 (4)	0.0457 (12)
N3	0.8088 (8)	0.2696 (3)	0.0867 (4)	0.0586 (14)
C1	0.7580 (7)	0.0168 (3)	0.0520 (4)	0.0345 (12)
C2	0.7868 (7)	0.0715 (3)	−0.0312 (4)	0.0335 (12)
C3	0.7853 (7)	0.0508 (3)	−0.1531 (4)	0.0367 (13)
C4	0.7516 (8)	−0.0159 (3)	−0.1891 (5)	0.0434 (14)
H4	0.7482	−0.0270	−0.2698	0.052*
C5	0.7223 (7)	−0.0670 (3)	−0.1039 (5)	0.0379 (13)
C6	0.7284 (7)	−0.0511 (3)	0.0134 (5)	0.0385 (13)
H6	0.7125	−0.0862	0.0693	0.046*
C7	0.7663 (8)	0.0288 (3)	0.1784 (5)	0.0416 (14)
H7	0.7498	−0.0096	0.2276	0.050*
C8	0.8018 (11)	0.0903 (3)	0.3598 (5)	0.0605 (18)
H8A	0.6761	0.0902	0.3910	0.073*
H8B	0.8681	0.0501	0.3915	0.073*
C9	0.8988 (12)	0.1539 (4)	0.3947 (6)	0.082 (2)
H9A	1.0323	0.1476	0.3849	0.099*
H9B	0.8770	0.1631	0.4783	0.099*
C10	0.9831 (9)	0.2676 (4)	0.3424 (6)	0.070 (2)
H10A	0.9534	0.3083	0.2962	0.105*
H10B	1.1013	0.2492	0.3180	0.105*
H10C	0.9903	0.2797	0.4253	0.105*
C11	0.6558 (9)	0.2434 (4)	0.3601 (6)	0.090 (3)
H11A	0.5584	0.2099	0.3456	0.135*
H11B	0.6293	0.2850	0.3154	0.135*
H11C	0.6620	0.2544	0.4435	0.135*
C12	0.8200 (8)	0.3284 (3)	0.0665 (5)	0.0430 (14)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0542 (5)	0.0340 (4)	0.0294 (4)	0.0032 (3)	0.0021 (3)	−0.0014 (3)
Br1	0.1060 (6)	0.0568 (4)	0.0339 (3)	−0.0027 (4)	0.0124 (3)	0.0077 (3)
Br2	0.0840 (5)	0.0438 (4)	0.0471 (4)	−0.0056 (3)	−0.0006 (3)	−0.0108 (3)
S1	0.0816 (13)	0.0378 (9)	0.0691 (12)	0.0009 (8)	0.0138 (10)	0.0055 (8)
O1	0.068 (3)	0.030 (2)	0.033 (2)	0.0007 (19)	0.0000 (19)	0.0004 (16)
N1	0.055 (3)	0.036 (3)	0.026 (2)	0.003 (2)	0.004 (2)	0.000 (2)
N2	0.063 (3)	0.040 (3)	0.034 (3)	−0.007 (2)	0.000 (2)	−0.008 (2)
N3	0.092 (4)	0.042 (3)	0.042 (3)	−0.002 (3)	−0.005 (3)	0.001 (2)
C1	0.037 (3)	0.041 (3)	0.026 (3)	0.007 (2)	0.003 (2)	0.000 (2)
C2	0.035 (3)	0.039 (3)	0.027 (3)	0.007 (2)	0.000 (2)	0.003 (2)
C3	0.037 (3)	0.046 (3)	0.027 (3)	0.008 (3)	0.007 (2)	0.007 (2)
C4	0.044 (3)	0.058 (4)	0.028 (3)	0.008 (3)	0.000 (3)	−0.010 (3)
C5	0.045 (3)	0.037 (3)	0.032 (3)	−0.001 (3)	0.000 (3)	−0.007 (2)
C6	0.044 (3)	0.039 (3)	0.033 (3)	0.006 (3)	0.002 (3)	0.003 (2)
C7	0.051 (4)	0.045 (3)	0.029 (3)	0.003 (3)	0.001 (3)	0.009 (3)
C8	0.107 (6)	0.048 (4)	0.027 (3)	−0.008 (4)	0.001 (3)	0.003 (3)
C9	0.145 (8)	0.068 (5)	0.034 (4)	−0.005 (5)	−0.002 (4)	0.003 (3)
C10	0.061 (5)	0.087 (5)	0.062 (5)	−0.011 (4)	−0.003 (4)	−0.022 (4)
C11	0.042 (4)	0.156 (8)	0.073 (5)	0.001 (4)	0.006 (4)	−0.060 (5)
C12	0.052 (4)	0.042 (4)	0.035 (3)	0.002 (3)	0.003 (3)	−0.004 (3)

Geometric parameters (Å, º)

Cu1—O1	1.908 (3)	C3—C4	1.364 (7)
Cu1—N3	1.927 (5)	C4—C5	1.390 (7)
Cu1—N1	1.932 (4)	C4—H4	0.9300
Cu1—N2	2.055 (4)	C5—C6	1.353 (7)
Br1—C3	1.880 (5)	C6—H6	0.9300
Br2—C5	1.901 (5)	C7—H7	0.9300
S1—C12	1.612 (6)	C8—C9	1.456 (9)
O1—C2	1.301 (6)	C8—H8A	0.9700
N1—C7	1.272 (6)	C8—H8B	0.9700
N1—C8	1.471 (6)	C9—H9A	0.9700
N2—C11	1.465 (7)	C9—H9B	0.9700
N2—C9	1.480 (8)	C10—H10A	0.9600
N2—C10	1.481 (7)	C10—H10B	0.9600
N3—C12	1.156 (6)	C10—H10C	0.9600
C1—C6	1.389 (7)	C11—H11A	0.9600
C1—C2	1.424 (7)	C11—H11B	0.9600
C1—C7	1.438 (7)	C11—H11C	0.9600
C2—C3	1.425 (7)
O1—Cu1—N3	91.61 (18)	C5—C6—C1	121.2 (5)
O1—Cu1—N1	92.55 (16)	C5—C6—H6	119.4
N3—Cu1—N1	173.3 (2)	C1—C6—H6	119.4
O1—Cu1—N2	174.47 (18)	N1—C7—C1	125.9 (5)
N3—Cu1—N2	91.87 (19)	N1—C7—H7	117.1
N1—Cu1—N2	84.39 (18)	C1—C7—H7	117.1
C2—O1—Cu1	127.7 (3)	C9—C8—N1	108.1 (5)
C7—N1—C8	118.9 (5)	C9—C8—H8A	110.1
C7—N1—Cu1	126.9 (4)	N1—C8—H8A	110.1
C8—N1—Cu1	114.1 (3)	C9—C8—H8B	110.1
C11—N2—C9	114.0 (6)	N1—C8—H8B	110.1
C11—N2—C10	108.9 (5)	H8A—C8—H8B	108.4
C9—N2—C10	104.6 (5)	C8—C9—N2	112.1 (6)
C11—N2—Cu1	110.3 (4)	C8—C9—H9A	109.2
C9—N2—Cu1	104.3 (3)	N2—C9—H9A	109.2
C10—N2—Cu1	114.8 (4)	C8—C9—H9B	109.2
C12—N3—Cu1	167.9 (5)	N2—C9—H9B	109.2
C6—C1—C2	120.8 (5)	H9A—C9—H9B	107.9
C6—C1—C7	117.5 (5)	N2—C10—H10A	109.5
C2—C1—C7	121.7 (5)	N2—C10—H10B	109.5
O1—C2—C1	124.7 (4)	H10A—C10—H10B	109.5
O1—C2—C3	120.1 (4)	N2—C10—H10C	109.5
C1—C2—C3	115.2 (5)	H10A—C10—H10C	109.5
C4—C3—C2	123.1 (5)	H10B—C10—H10C	109.5
C4—C3—Br1	118.1 (4)	N2—C11—H11A	109.5
C2—C3—Br1	118.8 (4)	N2—C11—H11B	109.5
C3—C4—C5	119.2 (5)	H11A—C11—H11B	109.5
C3—C4—H4	120.4	N2—C11—H11C	109.5
C5—C4—H4	120.4	H11A—C11—H11C	109.5
C6—C5—C4	120.6 (5)	H11B—C11—H11C	109.5
C6—C5—Br2	121.0 (4)	N3—C12—S1	179.6 (6)
C4—C5—Br2	118.3 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···Br2^i	0.96	2.88	3.676 (5)	141

Symmetry code: (i) −x+1, −y, −z.