Dichlorido{2,4-dibromo-6-[2-(ethyl­ammonio)ethyl­imino­meth­yl]phenolato}zinc(II)

In the title mononuclear zinc(II) complex, [ZnCl₂(C₁₁H₁₄Br₂N₂O)], the Zn atom is four-coordinated by the imine N and the O atoms of the Schiff base ligand, and by two terminal chloride anions, forming a tetra­hedral geometry. In the crystal structure, mol­ecules are linked through inter­molecular N—H...Cl hydrogen bonds, forming a two-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.008 Å
• R factor = 0.043
• wR factor = 0.108
• Data-to-parameter ratio = 21.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.85
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          8
PLAT431_ALERT_2_C Short Inter HL..A Contact  Br1    ..  Br2     ..       3.55 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H2B    ..  CL2     ..       2.84 Ang.

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      0.847
            Tmax scaled      0.369 Tmin scaled      0.323

   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
   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
   2 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.

Dichlorido{2,4-dibromo-6-[2-(ethylammonio)ethyliminomethyl]phenolato}zinc(II)

Crystal data

[ZnCl2(C11H14Br2N2O)]	F(000) = 944
Mr = 486.33	Dx = 1.956 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2367 reflections
a = 11.300 (1) Å	θ = 2.4–24.5°
b = 13.654 (2) Å	µ = 6.64 mm^−1
c = 10.729 (1) Å	T = 298 K
β = 94.024 (2)°	Block, colourless
V = 1651.3 (3) Å^3	0.18 × 0.17 × 0.15 mm
Z = 4

Data collection

Bruker SMART APEX CCD area diffractometer	3788 independent reflections
Radiation source: fine-focus sealed tube	2531 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.040
ω scans	θmax = 27.5°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→14
Tmin = 0.381, Tmax = 0.436	k = −14→17
9746 measured reflections	l = −12→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) = 0.108	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0415P)^2 + 2.1007P] where P = (Fo^2 + 2Fc^2)/3
3788 reflections	(Δ/σ)max < 0.001
173 parameters	Δρmax = 1.65 e Å^−3
0 restraints	Δρmin = −0.93 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	0.56674 (5)	0.18189 (4)	0.75895 (4)	0.03656 (15)
Br1	0.83439 (5)	−0.00040 (4)	1.04197 (5)	0.06222 (19)
Br2	1.03556 (7)	0.35971 (7)	1.20512 (7)	0.1003 (3)
Cl1	0.39876 (12)	0.17011 (9)	0.85849 (13)	0.0558 (3)
Cl2	0.54632 (13)	0.10873 (9)	0.57447 (10)	0.0552 (4)
O1	0.6987 (3)	0.1288 (2)	0.8597 (3)	0.0481 (8)
N1	0.6241 (3)	0.3213 (3)	0.7589 (3)	0.0347 (8)
N2	0.3857 (3)	0.3989 (3)	0.8034 (3)	0.0410 (9)
H2A	0.4157	0.4529	0.8420	0.049*
H2B	0.4111	0.3466	0.8488	0.049*
C1	0.7855 (4)	0.2853 (4)	0.9170 (4)	0.0419 (11)
C2	0.7725 (4)	0.1822 (4)	0.9281 (4)	0.0396 (10)
C3	0.8487 (4)	0.1358 (4)	1.0221 (4)	0.0455 (12)
C4	0.9259 (4)	0.1870 (5)	1.1010 (5)	0.0568 (14)
H4	0.9725	0.1543	1.1627	0.068*
C5	0.9346 (5)	0.2874 (5)	1.0890 (5)	0.0598 (15)
C6	0.8682 (5)	0.3358 (4)	0.9984 (5)	0.0543 (13)
H6	0.8772	0.4032	0.9897	0.065*
C7	0.7137 (4)	0.3463 (3)	0.8308 (4)	0.0408 (11)
H7	0.7356	0.4119	0.8276	0.049*
C8	0.5650 (4)	0.3984 (3)	0.6818 (4)	0.0421 (11)
H8A	0.5900	0.3934	0.5974	0.050*
H8B	0.5901	0.4618	0.7147	0.050*
C9	0.4314 (4)	0.3922 (3)	0.6780 (4)	0.0404 (11)
H9A	0.3976	0.4448	0.6262	0.049*
H9B	0.4059	0.3306	0.6397	0.049*
C10	0.2528 (5)	0.4030 (5)	0.7995 (6)	0.0677 (16)
H10A	0.2257	0.4658	0.7662	0.081*
H10B	0.2197	0.3522	0.7443	0.081*
C11	0.2102 (6)	0.3894 (6)	0.9263 (7)	0.095 (2)
H11A	0.2289	0.3243	0.9552	0.142*
H11B	0.1258	0.3989	0.9229	0.142*
H11C	0.2483	0.4361	0.9826	0.142*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0457 (3)	0.0277 (3)	0.0350 (3)	−0.0017 (2)	−0.0070 (2)	−0.0011 (2)
Br1	0.0552 (3)	0.0620 (4)	0.0669 (4)	0.0065 (3)	−0.0141 (3)	0.0194 (3)
Br2	0.0892 (5)	0.1379 (7)	0.0692 (4)	−0.0478 (5)	−0.0263 (4)	−0.0194 (4)
Cl1	0.0670 (8)	0.0390 (7)	0.0636 (8)	−0.0065 (6)	0.0206 (7)	0.0049 (6)
Cl2	0.0905 (10)	0.0414 (7)	0.0326 (6)	−0.0035 (7)	−0.0053 (6)	−0.0040 (5)
O1	0.052 (2)	0.0355 (18)	0.0535 (19)	0.0004 (16)	−0.0175 (16)	−0.0006 (15)
N1	0.042 (2)	0.0268 (18)	0.0351 (19)	−0.0011 (17)	0.0047 (16)	0.0011 (15)
N2	0.048 (2)	0.035 (2)	0.041 (2)	0.0032 (18)	0.0040 (18)	0.0013 (16)
C1	0.038 (2)	0.048 (3)	0.039 (2)	−0.005 (2)	0.000 (2)	−0.008 (2)
C2	0.035 (2)	0.049 (3)	0.034 (2)	−0.003 (2)	−0.0022 (19)	−0.004 (2)
C3	0.035 (2)	0.059 (3)	0.043 (3)	−0.001 (2)	−0.002 (2)	0.006 (2)
C4	0.042 (3)	0.084 (4)	0.043 (3)	−0.004 (3)	−0.008 (2)	0.004 (3)
C5	0.047 (3)	0.084 (4)	0.047 (3)	−0.016 (3)	−0.008 (2)	−0.016 (3)
C6	0.050 (3)	0.057 (3)	0.055 (3)	−0.015 (3)	−0.003 (2)	−0.013 (3)
C7	0.049 (3)	0.031 (2)	0.043 (3)	−0.007 (2)	0.006 (2)	−0.0054 (19)
C8	0.053 (3)	0.031 (2)	0.043 (3)	0.005 (2)	0.009 (2)	0.0044 (19)
C9	0.056 (3)	0.035 (2)	0.030 (2)	0.005 (2)	0.000 (2)	0.0027 (18)
C10	0.048 (3)	0.077 (4)	0.080 (4)	−0.001 (3)	0.013 (3)	0.007 (3)
C11	0.086 (5)	0.094 (6)	0.111 (6)	0.001 (4)	0.048 (5)	−0.004 (4)

Geometric parameters (Å, º)

Zn1—O1	1.921 (3)	C3—C4	1.364 (7)
Zn1—N1	2.011 (4)	C4—C5	1.382 (8)
Zn1—Cl2	2.2147 (12)	C4—H4	0.9300
Zn1—Cl1	2.2481 (14)	C5—C6	1.358 (8)
Br1—C3	1.881 (5)	C6—H6	0.9300
Br2—C5	1.905 (5)	C7—H7	0.9300
O1—C2	1.297 (5)	C8—C9	1.510 (7)
N1—C7	1.276 (6)	C8—H8A	0.9700
N1—C8	1.469 (5)	C8—H8B	0.9700
N2—C9	1.477 (5)	C9—H9A	0.9700
N2—C10	1.500 (6)	C9—H9B	0.9700
N2—H2A	0.9000	C10—C11	1.487 (8)
N2—H2B	0.9000	C10—H10A	0.9700
C1—C6	1.413 (6)	C10—H10B	0.9700
C1—C2	1.422 (7)	C11—H11A	0.9600
C1—C7	1.450 (7)	C11—H11B	0.9600
C2—C3	1.427 (6)	C11—H11C	0.9600
O1—Zn1—N1	96.91 (14)	C5—C6—C1	120.9 (5)
O1—Zn1—Cl2	111.13 (11)	C5—C6—H6	119.6
N1—Zn1—Cl2	116.12 (10)	C1—C6—H6	119.6
O1—Zn1—Cl1	110.71 (11)	N1—C7—C1	128.1 (4)
N1—Zn1—Cl1	110.52 (11)	N1—C7—H7	116.0
Cl2—Zn1—Cl1	110.72 (6)	C1—C7—H7	116.0
C2—O1—Zn1	123.3 (3)	N1—C8—C9	112.9 (4)
C7—N1—C8	117.3 (4)	N1—C8—H8A	109.0
C7—N1—Zn1	119.7 (3)	C9—C8—H8A	109.0
C8—N1—Zn1	123.0 (3)	N1—C8—H8B	109.0
C9—N2—C10	113.0 (4)	C9—C8—H8B	109.0
C9—N2—H2A	109.0	H8A—C8—H8B	107.8
C10—N2—H2A	109.0	N2—C9—C8	112.6 (4)
C9—N2—H2B	109.0	N2—C9—H9A	109.1
C10—N2—H2B	109.0	C8—C9—H9A	109.1
H2A—N2—H2B	107.8	N2—C9—H9B	109.1
C6—C1—C2	120.0 (5)	C8—C9—H9B	109.1
C6—C1—C7	115.5 (5)	H9A—C9—H9B	107.8
C2—C1—C7	124.5 (4)	C11—C10—N2	111.0 (5)
O1—C2—C1	125.2 (4)	C11—C10—H10A	109.4
O1—C2—C3	118.9 (4)	N2—C10—H10A	109.4
C1—C2—C3	116.0 (4)	C11—C10—H10B	109.4
C4—C3—C2	122.6 (5)	N2—C10—H10B	109.4
C4—C3—Br1	119.5 (4)	H10A—C10—H10B	108.0
C2—C3—Br1	117.8 (4)	C10—C11—H11A	109.5
C3—C4—C5	119.8 (5)	C10—C11—H11B	109.5
C3—C4—H4	120.1	H11A—C11—H11B	109.5
C5—C4—H4	120.1	C10—C11—H11C	109.5
C6—C5—C4	120.7 (5)	H11A—C11—H11C	109.5
C6—C5—Br2	119.4 (5)	H11B—C11—H11C	109.5
C4—C5—Br2	119.8 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···Cl2^i	0.90	2.34	3.221 (4)	167
N2—H2B···Cl1	0.90	2.42	3.181 (4)	143
N2—H2B···Cl2^ii	0.90	2.84	3.320 (4)	115

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