Dibromo­{4-chloro-2-[(2-diethyl­amino­ethyl­imino)meth­yl]phenolato}zinc(II)

The title compound, [ZnBr₂(C₁₃H₁₉ClN₂O)], is a mononuclear Schiff base zinc(II) complex. The Zn atom in the compound is four-coordinated by one imine N and one phenolate O atom of the Schiff base ligand and by two terminal bromide anions in a tetra­hedral geometry. In the crystal structure, mol­ecules are linked through inter­molecular N—H...O and C—H...Br hydrogen bonds, forming layers parallel to the bc plane.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.043
• wR factor = 0.113
• Data-to-parameter ratio = 21.4

checkCIF/PLATON results

No syntax errors found



Alert level C
CELLV02_ALERT_1_C  The supplied cell volume s.u. differs from that
            calculated from the cell parameter s.u.'s by > 2
            Calculated cell volume su =       2.92
            Cell volume su given      =       6.00
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.77
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Br2    -   Zn1     ..       8.98 su

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      0.769
            Tmax scaled      0.276 Tmin scaled      0.256

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

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 ALERT type 2 Indicator that the structure model may be wrong or deficient
   2 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, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); 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.

Dibromo{4-chloro-2-[(2-diethylaminoethylimino)methyl]phenolato}zinc(II)

Crystal data

[ZnBr2(C13H19ClN2O)]	F(000) = 944
Mr = 479.94	Dx = 1.823 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2913 reflections
a = 14.921 (1) Å	θ = 2.6–25.7°
b = 8.9624 (1) Å	µ = 6.12 mm^−1
c = 13.092 (2) Å	T = 298 K
β = 92.600 (1)°	Block, colourless
V = 1749.0 (6) Å^3	0.23 × 0.21 × 0.21 mm
Z = 4

Data collection

Bruker SMART APEX CCD area-detector diffractometer	4008 independent reflections
Radiation source: fine-focus sealed tube	2754 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
ω scans	θmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −17→19
Tmin = 0.333, Tmax = 0.360	k = −9→11
10219 measured reflections	l = −17→13

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.113	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ^2(Fo^2) + (0.0591P)^2] where P = (Fo^2 + 2Fc^2)/3
4008 reflections	(Δ/σ)max < 0.001
187 parameters	Δρmax = 0.89 e Å^−3
1 restraint	Δρmin = −0.67 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
Zn1	0.22962 (3)	0.23841 (5)	−0.08799 (3)	0.03693 (15)
Br1	0.24699 (4)	0.44459 (5)	−0.19705 (4)	0.06443 (19)
Br2	0.07924 (4)	0.18373 (6)	−0.05244 (4)	0.06643 (19)
Cl1	0.51403 (10)	−0.33621 (13)	0.13599 (10)	0.0644 (4)
O1	0.28871 (19)	0.0540 (3)	−0.12930 (19)	0.0370 (7)
N1	0.3032 (2)	0.2648 (3)	0.0440 (2)	0.0330 (7)
N2	0.1832 (2)	0.5518 (3)	0.1994 (2)	0.0330 (7)
C1	0.3717 (3)	0.0181 (4)	0.0320 (3)	0.0301 (8)
C2	0.3414 (3)	−0.0274 (4)	−0.0673 (3)	0.0311 (8)
C3	0.3680 (3)	−0.1692 (4)	−0.0999 (3)	0.0393 (10)
H3	0.3500	−0.2009	−0.1653	0.047*
C4	0.4196 (3)	−0.2627 (4)	−0.0387 (3)	0.0420 (10)
H4	0.4361	−0.3559	−0.0628	0.050*
C5	0.4471 (3)	−0.2182 (4)	0.0587 (3)	0.0405 (10)
C6	0.4254 (3)	−0.0804 (4)	0.0934 (3)	0.0352 (9)
H6	0.4460	−0.0505	0.1583	0.042*
C7	0.3547 (3)	0.1612 (4)	0.0789 (3)	0.0325 (8)
H7	0.3848	0.1797	0.1414	0.039*
C8	0.2966 (3)	0.4013 (4)	0.1050 (3)	0.0386 (9)
H8A	0.3174	0.4863	0.0670	0.046*
H8B	0.3333	0.3925	0.1678	0.046*
C9	0.1987 (3)	0.4224 (4)	0.1294 (3)	0.0351 (9)
H9A	0.1637	0.4374	0.0660	0.042*
H9B	0.1773	0.3320	0.1609	0.042*
C10	0.2195 (3)	0.6981 (4)	0.1604 (3)	0.0406 (10)
H10A	0.2103	0.7752	0.2109	0.049*
H10B	0.2836	0.6882	0.1530	0.049*
C11	0.1764 (4)	0.7467 (5)	0.0598 (4)	0.0593 (13)
H11A	0.1824	0.6689	0.0101	0.089*
H11B	0.2054	0.8355	0.0369	0.089*
H11C	0.1140	0.7668	0.0681	0.089*
C12	0.0857 (3)	0.5592 (4)	0.2221 (3)	0.0429 (10)
H12A	0.0669	0.4625	0.2466	0.051*
H12B	0.0512	0.5802	0.1592	0.051*
C13	0.0647 (4)	0.6762 (6)	0.3005 (4)	0.0689 (15)
H13A	0.1026	0.6617	0.3609	0.103*
H13B	0.0030	0.6676	0.3175	0.103*
H13C	0.0751	0.7735	0.2729	0.103*
H2	0.216 (2)	0.529 (4)	0.2572 (19)	0.035 (11)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0493 (3)	0.0314 (2)	0.0295 (2)	0.00799 (19)	−0.0044 (2)	−0.00309 (18)
Br1	0.1017 (5)	0.0405 (3)	0.0513 (3)	0.0169 (2)	0.0062 (3)	0.0144 (2)
Br2	0.0464 (3)	0.0854 (4)	0.0673 (3)	−0.0053 (3)	0.0012 (2)	−0.0276 (3)
Cl1	0.0789 (10)	0.0502 (7)	0.0624 (8)	0.0257 (6)	−0.0168 (7)	0.0073 (6)
O1	0.0523 (19)	0.0307 (13)	0.0273 (13)	0.0088 (12)	−0.0062 (12)	−0.0052 (10)
N1	0.043 (2)	0.0278 (16)	0.0285 (15)	0.0025 (13)	−0.0018 (14)	−0.0047 (12)
N2	0.045 (2)	0.0274 (15)	0.0256 (15)	0.0017 (13)	−0.0039 (14)	−0.0034 (12)
C1	0.031 (2)	0.0302 (18)	0.0294 (18)	0.0021 (15)	0.0025 (15)	−0.0013 (14)
C2	0.035 (2)	0.0276 (19)	0.0305 (19)	0.0008 (15)	0.0027 (16)	−0.0011 (15)
C3	0.046 (3)	0.037 (2)	0.034 (2)	0.0075 (18)	−0.0022 (18)	−0.0070 (17)
C4	0.047 (3)	0.029 (2)	0.050 (2)	0.0075 (17)	0.000 (2)	−0.0067 (17)
C5	0.043 (3)	0.032 (2)	0.046 (2)	0.0071 (17)	−0.0035 (19)	0.0094 (17)
C6	0.036 (2)	0.039 (2)	0.0310 (19)	0.0025 (16)	−0.0025 (16)	0.0006 (16)
C7	0.034 (2)	0.037 (2)	0.0263 (18)	−0.0048 (16)	0.0000 (15)	−0.0037 (15)
C8	0.052 (3)	0.0297 (19)	0.034 (2)	0.0008 (17)	−0.0032 (18)	−0.0066 (16)
C9	0.050 (3)	0.0247 (18)	0.0301 (19)	−0.0002 (16)	−0.0018 (17)	−0.0071 (14)
C10	0.049 (3)	0.0239 (18)	0.049 (2)	−0.0031 (16)	0.002 (2)	−0.0028 (16)
C11	0.059 (4)	0.053 (3)	0.066 (3)	−0.002 (2)	0.004 (3)	0.028 (2)
C12	0.052 (3)	0.041 (2)	0.036 (2)	−0.0006 (19)	0.0072 (19)	0.0003 (17)
C13	0.086 (4)	0.064 (3)	0.059 (3)	0.014 (3)	0.026 (3)	−0.010 (3)

Geometric parameters (Å, º)

Zn1—O1	1.961 (2)	C5—C6	1.360 (5)
Zn1—N1	2.018 (3)	C6—H6	0.9300
Zn1—Br1	2.3567 (7)	C7—H7	0.9300
Zn1—Br2	2.3636 (9)	C8—C9	1.520 (6)
Cl1—C5	1.746 (4)	C8—H8A	0.9700
O1—C2	1.323 (4)	C8—H8B	0.9700
N1—C7	1.277 (5)	C9—H9A	0.9700
N1—C8	1.466 (4)	C9—H9B	0.9700
N2—C12	1.500 (6)	C10—C11	1.504 (6)
N2—C9	1.503 (4)	C10—H10A	0.9700
N2—C10	1.516 (5)	C10—H10B	0.9700
N2—H2	0.91 (3)	C11—H11A	0.9600
C1—C2	1.417 (5)	C11—H11B	0.9600
C1—C6	1.417 (5)	C11—H11C	0.9600
C1—C7	1.449 (5)	C12—C13	1.510 (6)
C2—C3	1.404 (5)	C12—H12A	0.9700
C3—C4	1.372 (5)	C12—H12B	0.9700
C3—H3	0.9300	C13—H13A	0.9600
C4—C5	1.380 (6)	C13—H13B	0.9600
C4—H4	0.9300	C13—H13C	0.9600
O1—Zn1—N1	95.81 (11)	N1—C8—C9	107.9 (3)
O1—Zn1—Br1	115.51 (9)	N1—C8—H8A	110.1
N1—Zn1—Br1	110.86 (9)	C9—C8—H8A	110.1
O1—Zn1—Br2	108.80 (9)	N1—C8—H8B	110.1
N1—Zn1—Br2	109.88 (10)	C9—C8—H8B	110.1
Br1—Zn1—Br2	114.41 (3)	H8A—C8—H8B	108.4
C2—O1—Zn1	123.9 (2)	N2—C9—C8	113.6 (3)
C7—N1—C8	117.8 (3)	N2—C9—H9A	108.9
C7—N1—Zn1	121.1 (2)	C8—C9—H9A	108.9
C8—N1—Zn1	121.1 (2)	N2—C9—H9B	108.9
C12—N2—C9	109.4 (3)	C8—C9—H9B	108.9
C12—N2—C10	113.1 (3)	H9A—C9—H9B	107.7
C9—N2—C10	113.3 (3)	C11—C10—N2	113.7 (3)
C12—N2—H2	110 (3)	C11—C10—H10A	108.8
C9—N2—H2	104 (2)	N2—C10—H10A	108.8
C10—N2—H2	107 (2)	C11—C10—H10B	108.8
C2—C1—C6	119.3 (3)	N2—C10—H10B	108.8
C2—C1—C7	126.0 (3)	H10A—C10—H10B	107.7
C6—C1—C7	114.6 (3)	C10—C11—H11A	109.5
O1—C2—C3	118.7 (3)	C10—C11—H11B	109.5
O1—C2—C1	124.1 (3)	H11A—C11—H11B	109.5
C3—C2—C1	117.2 (3)	C10—C11—H11C	109.5
C4—C3—C2	122.3 (4)	H11A—C11—H11C	109.5
C4—C3—H3	118.8	H11B—C11—H11C	109.5
C2—C3—H3	118.8	N2—C12—C13	113.5 (4)
C3—C4—C5	119.9 (3)	N2—C12—H12A	108.9
C3—C4—H4	120.0	C13—C12—H12A	108.9
C5—C4—H4	120.0	N2—C12—H12B	108.9
C6—C5—C4	120.4 (3)	C13—C12—H12B	108.9
C6—C5—Cl1	119.7 (3)	H12A—C12—H12B	107.7
C4—C5—Cl1	119.9 (3)	C12—C13—H13A	109.5
C5—C6—C1	120.9 (3)	C12—C13—H13B	109.5
C5—C6—H6	119.6	H13A—C13—H13B	109.5
C1—C6—H6	119.6	C12—C13—H13C	109.5
N1—C7—C1	127.3 (3)	H13A—C13—H13C	109.5
N1—C7—H7	116.3	H13B—C13—H13C	109.5
C1—C7—H7	116.3

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1^i	0.91 (3)	1.95 (3)	2.843 (4)	170 (3)
C10—H10A···Br1^ii	0.97	2.83	3.719 (4)	153
C11—H11C···Br2^iii	0.96	2.91	3.862 (4)	169

Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+3/2, z+1/2; (iii) −x, −y+1, −z.