Azido­{2-bromo-4-chloro-6-[2-(diethyl­amino)ethyl­imino­meth­yl]phenolato-κ³N,N′,O}copper(II)

The title compound, [Cu(C₁₃H₁₇BrClN₂O)(N₃)], is isostructural with the nickel(II) complex reported by Tang [(2006), Acta Cryst. E62, m2629–m2630]. The Cu atom in the complex is coordinated by one O and two N atoms of the Schiff base ligand and by one N atom of the azide ligand in a slightly distorted square-planar configuration. The mol­ecules are linked by inter­molecular C—H...N hydrogen bonds, forming chains running along the c axis.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.036
• wR factor = 0.087
• Data-to-parameter ratio = 18.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.84
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N3     -   N4      ..       5.34 su
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         N3
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N4

Alert level G
ABSTM02_ALERT_3_G  When printed, the submitted absorption T values will be
            replaced by the scaled T values. Since the ratio of scaled T's
            is identical to the ratio of reported T values, the scaling
            does not imply a change to the absorption corrections used in
            the study.
            Ratio of Tmax expected/reported      0.836
            Tmax scaled      0.353 Tmin scaled      0.311

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

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 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
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); 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: SHELXL97.

Azido[2-bromo-4-chloro-6-[2-(diethylamino)ethyliminomethyl]phenolato- κ³N,N',O]copper(II)

Crystal data

[Cu(C13H17BrClN2O)(N3)]	F(000) = 876
Mr = 438.22	Dx = 1.736 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2543 reflections
a = 17.541 (1) Å	θ = 2.4–24.9°
b = 9.721 (1) Å	µ = 3.85 mm^−1
c = 9.843 (2) Å	T = 298 K
β = 92.465 (2)°	Block, blue
V = 1676.8 (4) Å^3	0.32 × 0.28 × 0.27 mm
Z = 4

Data collection

Bruker SMART CCD area-detector diffractometer	3637 independent reflections
Radiation source: fine-focus sealed tube	2432 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.047
ω scans	θmax = 27.0°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −22→22
Tmin = 0.372, Tmax = 0.423	k = −12→12
13720 measured reflections	l = −12→12

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.087	H-atom parameters constrained
S = 0.94	w = 1/[σ^2(Fo^2) + (0.0464P)^2] where P = (Fo^2 + 2Fc^2)/3
3637 reflections	(Δ/σ)max < 0.001
201 parameters	Δρmax = 0.39 e Å^−3
0 restraints	Δρmin = −0.51 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	0.21133 (2)	0.29941 (4)	0.80571 (4)	0.04024 (13)
Br1	0.35047 (2)	−0.10717 (3)	0.94197 (4)	0.06227 (15)
Cl1	0.50886 (5)	0.20306 (10)	1.33027 (10)	0.0621 (3)
O1	0.27742 (12)	0.1633 (2)	0.8819 (2)	0.0414 (5)
N1	0.26605 (15)	0.4471 (2)	0.8984 (3)	0.0417 (6)
N2	0.13747 (15)	0.4536 (2)	0.7390 (2)	0.0384 (6)
N3	0.1566 (2)	0.1673 (3)	0.6910 (4)	0.0745 (11)
N4	0.17019 (17)	0.0465 (3)	0.6894 (3)	0.0520 (7)
N5	0.1801 (2)	−0.0699 (3)	0.6821 (3)	0.0723 (10)
C1	0.34856 (18)	0.3057 (3)	1.0428 (3)	0.0404 (7)
C2	0.32883 (18)	0.1793 (3)	0.9793 (3)	0.0371 (7)
C3	0.37076 (19)	0.0632 (3)	1.0281 (3)	0.0431 (8)
C4	0.4246 (2)	0.0699 (3)	1.1335 (3)	0.0489 (8)
H4	0.4503	−0.0089	1.1634	0.059*
C5	0.44021 (19)	0.1959 (4)	1.1946 (3)	0.0463 (8)
C6	0.40428 (19)	0.3111 (3)	1.1512 (3)	0.0465 (8)
H6	0.4161	0.3949	1.1927	0.056*
C7	0.31647 (19)	0.4336 (3)	0.9961 (3)	0.0448 (8)
H7	0.3335	0.5133	1.0401	0.054*
C8	0.2392 (2)	0.5841 (3)	0.8583 (4)	0.0502 (9)
H8A	0.2650	0.6150	0.7786	0.060*
H8B	0.2498	0.6492	0.9314	0.060*
C9	0.15442 (19)	0.5746 (3)	0.8274 (3)	0.0452 (8)
H9A	0.1279	0.5656	0.9114	0.054*
H9B	0.1366	0.6578	0.7818	0.054*
C10	0.0556 (2)	0.4175 (4)	0.7430 (4)	0.0534 (9)
H10A	0.0423	0.3566	0.6675	0.064*
H10B	0.0253	0.5005	0.7313	0.064*
C11	0.0354 (2)	0.3480 (5)	0.8745 (4)	0.0811 (13)
H11A	0.0588	0.2588	0.8798	0.122*
H11B	−0.0190	0.3384	0.8770	0.122*
H11C	0.0537	0.4029	0.9502	0.122*
C12	0.1589 (2)	0.4783 (4)	0.5953 (3)	0.0531 (9)
H12A	0.1486	0.3948	0.5439	0.064*
H12B	0.2135	0.4941	0.5957	0.064*
C13	0.1199 (3)	0.5959 (4)	0.5206 (4)	0.0691 (12)
H13A	0.0657	0.5831	0.5202	0.104*
H13B	0.1361	0.5984	0.4287	0.104*
H13C	0.1332	0.6809	0.5652	0.104*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cu1	0.0420 (2)	0.0292 (2)	0.0487 (2)	−0.00113 (17)	−0.00795 (18)	−0.00475 (16)
Br1	0.0645 (3)	0.0353 (2)	0.0849 (3)	0.00553 (17)	−0.0210 (2)	−0.01254 (18)
Cl1	0.0510 (6)	0.0735 (6)	0.0599 (6)	0.0081 (5)	−0.0202 (4)	−0.0167 (5)
O1	0.0428 (13)	0.0313 (11)	0.0491 (13)	−0.0022 (9)	−0.0087 (11)	−0.0063 (10)
N1	0.0390 (16)	0.0295 (13)	0.0561 (17)	−0.0023 (11)	−0.0026 (14)	−0.0046 (12)
N2	0.0440 (17)	0.0330 (13)	0.0379 (14)	0.0003 (12)	−0.0011 (12)	−0.0036 (11)
N3	0.083 (3)	0.0388 (18)	0.097 (3)	0.0080 (16)	−0.045 (2)	−0.0181 (17)
N4	0.061 (2)	0.0494 (19)	0.0445 (17)	−0.0113 (15)	−0.0108 (14)	−0.0051 (14)
N5	0.115 (3)	0.0395 (18)	0.062 (2)	−0.0098 (19)	−0.003 (2)	−0.0086 (15)
C1	0.0355 (18)	0.0399 (17)	0.0457 (19)	−0.0019 (14)	0.0003 (14)	−0.0096 (15)
C2	0.0317 (17)	0.0379 (18)	0.0419 (18)	−0.0015 (13)	0.0025 (14)	−0.0045 (14)
C3	0.0389 (19)	0.0323 (16)	0.058 (2)	0.0002 (14)	−0.0009 (16)	−0.0078 (15)
C4	0.043 (2)	0.0458 (19)	0.057 (2)	0.0024 (16)	−0.0085 (17)	−0.0031 (16)
C5	0.0369 (19)	0.058 (2)	0.0437 (19)	0.0034 (17)	−0.0055 (15)	−0.0080 (17)
C6	0.0374 (19)	0.048 (2)	0.053 (2)	−0.0005 (15)	−0.0057 (16)	−0.0167 (16)
C7	0.042 (2)	0.0336 (17)	0.058 (2)	−0.0037 (14)	−0.0032 (17)	−0.0119 (15)
C8	0.060 (2)	0.0255 (16)	0.064 (2)	−0.0025 (15)	−0.0076 (18)	−0.0018 (15)
C9	0.053 (2)	0.0349 (17)	0.047 (2)	0.0060 (15)	−0.0033 (16)	−0.0056 (14)
C10	0.043 (2)	0.053 (2)	0.063 (2)	−0.0007 (17)	−0.0072 (18)	0.0011 (18)
C11	0.059 (3)	0.096 (3)	0.089 (3)	−0.014 (2)	0.010 (2)	0.017 (3)
C12	0.070 (3)	0.046 (2)	0.043 (2)	0.0040 (18)	0.0064 (18)	−0.0044 (16)
C13	0.105 (3)	0.056 (2)	0.046 (2)	0.009 (2)	0.002 (2)	0.0079 (18)

Geometric parameters (Å, º)

Cu1—O1	1.893 (2)	C5—C6	1.345 (4)
Cu1—N1	1.934 (3)	C6—H6	0.9300
Cu1—N3	1.937 (3)	C7—H7	0.9300
Cu1—N2	2.070 (3)	C8—C9	1.508 (5)
Br1—C3	1.888 (3)	C8—H8A	0.9700
Cl1—C5	1.761 (3)	C8—H8B	0.9700
O1—C2	1.297 (3)	C9—H9A	0.9700
N1—C7	1.285 (4)	C9—H9B	0.9700
N1—C8	1.462 (4)	C10—C11	1.516 (5)
N2—C10	1.481 (4)	C10—H10A	0.9700
N2—C9	1.485 (4)	C10—H10B	0.9700
N2—C12	1.499 (4)	C11—H11A	0.9600
N3—N4	1.198 (4)	C11—H11B	0.9600
N4—N5	1.148 (4)	C11—H11C	0.9600
C1—C2	1.415 (4)	C12—C13	1.507 (5)
C1—C6	1.417 (4)	C12—H12A	0.9700
C1—C7	1.433 (4)	C12—H12B	0.9700
C2—C3	1.419 (4)	C13—H13A	0.9600
C3—C4	1.375 (5)	C13—H13B	0.9600
C4—C5	1.386 (4)	C13—H13C	0.9600
C4—H4	0.9300
O1—Cu1—N1	92.80 (10)	C1—C7—H7	117.4
O1—Cu1—N3	92.70 (11)	N1—C8—C9	107.6 (3)
N1—Cu1—N3	172.17 (13)	N1—C8—H8A	110.2
O1—Cu1—N2	175.14 (9)	C9—C8—H8A	110.2
N1—Cu1—N2	84.44 (10)	N1—C8—H8B	110.2
N3—Cu1—N2	90.45 (12)	C9—C8—H8B	110.2
C2—O1—Cu1	127.15 (19)	H8A—C8—H8B	108.5
C7—N1—C8	119.9 (3)	N2—C9—C8	109.7 (3)
C7—N1—Cu1	126.1 (2)	N2—C9—H9A	109.7
C8—N1—Cu1	113.7 (2)	C8—C9—H9A	109.7
C10—N2—C9	110.0 (3)	N2—C9—H9B	109.7
C10—N2—C12	110.2 (3)	C8—C9—H9B	109.7
C9—N2—C12	112.0 (2)	H9A—C9—H9B	108.2
C10—N2—Cu1	114.48 (19)	N2—C10—C11	113.0 (3)
C9—N2—Cu1	106.32 (18)	N2—C10—H10A	109.0
C12—N2—Cu1	103.66 (19)	C11—C10—H10A	109.0
N4—N3—Cu1	124.3 (3)	N2—C10—H10B	109.0
N5—N4—N3	176.2 (4)	C11—C10—H10B	109.0
C2—C1—C6	120.9 (3)	H10A—C10—H10B	107.8
C2—C1—C7	121.8 (3)	C10—C11—H11A	109.5
C6—C1—C7	117.2 (3)	C10—C11—H11B	109.5
O1—C2—C1	125.4 (3)	H11A—C11—H11B	109.5
O1—C2—C3	119.3 (3)	C10—C11—H11C	109.5
C1—C2—C3	115.3 (3)	H11A—C11—H11C	109.5
C4—C3—C2	123.2 (3)	H11B—C11—H11C	109.5
C4—C3—Br1	119.4 (2)	N2—C12—C13	117.1 (3)
C2—C3—Br1	117.4 (2)	N2—C12—H12A	108.0
C3—C4—C5	119.0 (3)	C13—C12—H12A	108.0
C3—C4—H4	120.5	N2—C12—H12B	108.0
C5—C4—H4	120.5	C13—C12—H12B	108.0
C6—C5—C4	121.1 (3)	H12A—C12—H12B	107.3
C6—C5—Cl1	120.2 (3)	C12—C13—H13A	109.5
C4—C5—Cl1	118.6 (3)	C12—C13—H13B	109.5
C5—C6—C1	120.4 (3)	H13A—C13—H13B	109.5
C5—C6—H6	119.8	C12—C13—H13C	109.5
C1—C6—H6	119.8	H13A—C13—H13C	109.5
N1—C7—C1	125.2 (3)	H13B—C13—H13C	109.5
N1—C7—H7	117.4

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13B···N5^i	0.96	2.59	3.547 (5)	172

Symmetry code: (i) x, −y+1/2, z−1/2.