Dibromido{2,4-dichloro-6-[3-(dimethyl­ammonio)propyl­imino­meth­yl]phenolato}zinc(II)

Li, L.-Z.; Wang, L.-H.

doi:10.1107/S1600536807014201

Dibromido{2,4-dichloro-6-[3-(dimethylammonio)propyliminomethyl]phenolato}zinc(II)

The title compound, [ZnBr₂(C₁₂H₁₆Cl₂N₂O)], is a mononuclear Zn^II complex. The Zn^II ion is four-coordinated in a tetrahedral geometry by one Schiff base ligand and by two Br atoms. In the crystal structure, molecules are linked through N—H

Br, C—H

Br and C—H

O intermolecular hydrogen bonds, forming layers parallel to the ab plane.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807014201/bh2090sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807014201/bh2090Isup2.hkl Contains datablock I

CCDC reference: 646723

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.008 Å
R factor = 0.050
wR factor = 0.111
Data-to-parameter ratio = 21.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Br2    -   Zn1     ..       5.16 su
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
   2 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
   1 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
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Computing details top

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

Dibromido{2,4-dichloro-6-[3- (dimethylammonio)propyliminomethyl]phenolato}zinc(II) top

Crystal data top

[ZnBr₂(C₁₂H₁₆Cl₂N₂O)]	F(000) = 1952
M_r = 500.36	D_x = 1.903 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4408 reflections
a = 8.235 (1) Å	θ = 2.7–24.9°
b = 14.573 (2) Å	µ = 6.29 mm⁻¹
c = 29.099 (3) Å	T = 298 K
V = 3492.1 (7) Å³	Block, colourless
Z = 8	0.26 × 0.22 × 0.21 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	4017 independent reflections
Radiation source: fine-focus sealed tube	2737 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.069
ω scans	θ_max = 27.5°, θ_min = 1.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.222, T_max = 0.268	k = −18→18
27938 measured reflections	l = −37→37

Refinement top

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.111	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0315P)² + 13.4509P] where P = (F_o² + 2F_c²)/3
4017 reflections	(Δ/σ)_max < 0.001
186 parameters	Δρ_max = 1.64 e Å⁻³
1 restraint	Δρ_min = −1.61 e Å⁻³

Special details top

Experimental. Selected IR data (cm^-1): 3454 (b,w), 3025 (m), 2927 (m), 1613 (versus), 1545 (m), 1470 (m), 1180 (m), 775 (m).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Zn1	0.16743 (8)	1.11515 (4)	0.09309 (2)	0.03831 (17)
Br1	0.42794 (8)	1.15773 (5)	0.06616 (3)	0.0671 (2)
Br2	−0.03690 (7)	1.13273 (4)	0.03645 (2)	0.04781 (17)
Cl1	0.0340 (2)	1.31068 (10)	0.22081 (6)	0.0643 (5)
Cl2	0.2263 (3)	1.04558 (15)	0.33632 (6)	0.0826 (6)
O1	0.1042 (5)	1.1771 (2)	0.14946 (13)	0.0492 (10)
N1	0.1687 (5)	0.9885 (3)	0.12102 (15)	0.0358 (10)
N2	0.6156 (6)	0.8493 (4)	0.0728 (2)	0.0534 (14)
C1	0.1667 (7)	1.0502 (3)	0.19920 (19)	0.0386 (12)
C2	0.1254 (7)	1.1433 (4)	0.19005 (18)	0.0386 (12)
C3	0.1008 (7)	1.1986 (4)	0.22938 (19)	0.0414 (13)
C4	0.1296 (8)	1.1701 (4)	0.2733 (2)	0.0525 (16)
H4	0.1154	1.2098	0.2980	0.063*
C5	0.1805 (8)	1.0802 (4)	0.28035 (19)	0.0495 (15)
C6	0.1937 (7)	1.0215 (4)	0.2447 (2)	0.0485 (15)
H6	0.2213	0.9607	0.2504	0.058*
C7	0.1715 (6)	0.9788 (3)	0.16451 (19)	0.0379 (12)
H7	0.1772	0.9188	0.1753	0.045*
C8	0.1665 (6)	0.9059 (3)	0.0923 (2)	0.0401 (13)
H8A	0.0761	0.9096	0.0710	0.048*
H8B	0.1500	0.8525	0.1116	0.048*
C9	0.3235 (6)	0.8945 (4)	0.06537 (18)	0.0381 (12)
H9A	0.3120	0.8445	0.0436	0.046*
H9B	0.3461	0.9501	0.0482	0.046*
C10	0.4615 (6)	0.8747 (4)	0.09733 (18)	0.0355 (12)
H10A	0.4308	0.8248	0.1176	0.043*
H10B	0.4814	0.9284	0.1162	0.043*
C11	0.7339 (8)	0.8086 (5)	0.1053 (3)	0.080 (2)
H11A	0.8274	0.7876	0.0886	0.120*
H11B	0.6846	0.7577	0.1209	0.120*
H11C	0.7665	0.8540	0.1273	0.120*
C12	0.6874 (9)	0.9289 (6)	0.0478 (2)	0.077 (2)
H12A	0.7210	0.9747	0.0696	0.116*
H12B	0.6078	0.9546	0.0275	0.116*
H12C	0.7797	0.9088	0.0304	0.116*
H2	0.591 (8)	0.803 (3)	0.0533 (19)	0.080*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0459 (4)	0.0301 (3)	0.0390 (3)	0.0054 (3)	−0.0046 (3)	−0.0011 (3)
Br1	0.0467 (4)	0.0446 (4)	0.1100 (6)	−0.0110 (3)	−0.0004 (4)	−0.0054 (4)
Br2	0.0490 (3)	0.0480 (3)	0.0464 (3)	0.0074 (3)	−0.0128 (3)	−0.0077 (3)
Cl1	0.0966 (14)	0.0358 (8)	0.0603 (10)	0.0096 (8)	0.0072 (10)	−0.0094 (7)
Cl2	0.1192 (17)	0.0912 (14)	0.0375 (9)	−0.0053 (13)	0.0030 (10)	0.0185 (9)
O1	0.078 (3)	0.034 (2)	0.035 (2)	0.017 (2)	−0.006 (2)	−0.0012 (17)
N1	0.040 (2)	0.025 (2)	0.042 (3)	0.0051 (19)	−0.002 (2)	−0.0041 (18)
N2	0.035 (3)	0.050 (3)	0.075 (4)	0.000 (2)	−0.001 (3)	−0.030 (3)
C1	0.041 (3)	0.034 (3)	0.041 (3)	0.002 (2)	0.000 (3)	0.003 (2)
C2	0.042 (3)	0.034 (3)	0.040 (3)	0.001 (2)	−0.003 (3)	−0.003 (2)
C3	0.047 (3)	0.035 (3)	0.043 (3)	−0.003 (3)	0.002 (3)	−0.004 (2)
C4	0.068 (4)	0.050 (4)	0.039 (3)	−0.010 (3)	0.009 (3)	−0.010 (3)
C5	0.061 (4)	0.054 (4)	0.034 (3)	−0.009 (3)	0.007 (3)	0.007 (3)
C6	0.057 (4)	0.039 (3)	0.049 (3)	−0.002 (3)	0.007 (3)	0.007 (3)
C7	0.039 (3)	0.026 (3)	0.049 (3)	0.005 (2)	0.002 (3)	0.003 (2)
C8	0.035 (3)	0.033 (3)	0.053 (3)	0.000 (2)	−0.009 (3)	−0.008 (2)
C9	0.041 (3)	0.032 (3)	0.041 (3)	0.001 (2)	−0.003 (3)	−0.005 (2)
C10	0.029 (3)	0.034 (3)	0.044 (3)	0.001 (2)	0.004 (2)	0.000 (2)
C11	0.040 (4)	0.056 (4)	0.143 (7)	0.011 (3)	−0.014 (5)	−0.010 (5)
C12	0.062 (5)	0.115 (7)	0.054 (4)	−0.015 (5)	0.020 (4)	−0.004 (4)

Geometric parameters (Å, º) top

Zn1—O1	1.943 (4)	C4—H4	0.9300
Zn1—N1	2.016 (4)	C5—C6	1.348 (8)
Zn1—Br1	2.3668 (10)	C6—H6	0.9300
Zn1—Br2	2.3694 (9)	C7—H7	0.9300
Cl1—C3	1.742 (6)	C8—C9	1.521 (7)
Cl2—C5	1.746 (6)	C8—H8A	0.9700
O1—C2	1.291 (6)	C8—H8B	0.9700
N1—C7	1.274 (6)	C9—C10	1.496 (7)
N1—C8	1.466 (6)	C9—H9A	0.9700
N2—C11	1.481 (9)	C9—H9B	0.9700
N2—C12	1.491 (9)	C10—H10A	0.9700
N2—C10	1.502 (7)	C10—H10B	0.9700
N2—H2	0.91 (5)	C11—H11A	0.9600
C1—C6	1.407 (8)	C11—H11B	0.9600
C1—C2	1.424 (7)	C11—H11C	0.9600
C1—C7	1.450 (7)	C12—H12A	0.9600
C2—C3	1.414 (7)	C12—H12B	0.9600
C3—C4	1.365 (8)	C12—H12C	0.9600
C4—C5	1.390 (9)

O1—Zn1—N1	94.94 (17)	N1—C7—C1	127.7 (5)
O1—Zn1—Br1	113.62 (14)	N1—C7—H7	116.2
N1—Zn1—Br1	111.64 (13)	C1—C7—H7	116.2
O1—Zn1—Br2	110.28 (12)	N1—C8—C9	111.9 (4)
N1—Zn1—Br2	112.53 (13)	N1—C8—H8A	109.2
Br1—Zn1—Br2	112.64 (4)	C9—C8—H8A	109.2
C2—O1—Zn1	124.0 (3)	N1—C8—H8B	109.2
C7—N1—C8	118.4 (4)	C9—C8—H8B	109.2
C7—N1—Zn1	120.2 (4)	H8A—C8—H8B	107.9
C8—N1—Zn1	121.4 (3)	C10—C9—C8	110.3 (4)
C11—N2—C12	111.2 (5)	C10—C9—H9A	109.6
C11—N2—C10	110.6 (5)	C8—C9—H9A	109.6
C12—N2—C10	112.0 (5)	C10—C9—H9B	109.6
C11—N2—H2	104 (5)	C8—C9—H9B	109.6
C12—N2—H2	111 (5)	H9A—C9—H9B	108.1
C10—N2—H2	107 (5)	C9—C10—N2	113.2 (4)
C6—C1—C2	119.8 (5)	C9—C10—H10A	108.9
C6—C1—C7	116.0 (5)	N2—C10—H10A	108.9
C2—C1—C7	124.1 (5)	C9—C10—H10B	108.9
O1—C2—C3	120.3 (5)	N2—C10—H10B	108.9
O1—C2—C1	124.5 (5)	H10A—C10—H10B	107.8
C3—C2—C1	115.2 (5)	N2—C11—H11A	109.5
C4—C3—C2	124.0 (5)	N2—C11—H11B	109.5
C4—C3—Cl1	118.3 (4)	H11A—C11—H11B	109.5
C2—C3—Cl1	117.6 (4)	N2—C11—H11C	109.5
C3—C4—C5	118.5 (5)	H11A—C11—H11C	109.5
C3—C4—H4	120.7	H11B—C11—H11C	109.5
C5—C4—H4	120.7	N2—C12—H12A	109.5
C6—C5—C4	120.6 (5)	N2—C12—H12B	109.5
C6—C5—Cl2	121.1 (5)	H12A—C12—H12B	109.5
C4—C5—Cl2	118.3 (5)	N2—C12—H12C	109.5
C5—C6—C1	121.5 (5)	H12A—C12—H12C	109.5
C5—C6—H6	119.2	H12B—C12—H12C	109.5
C1—C6—H6	119.2

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···Br2ⁱ	0.91 (5)	2.57 (4)	3.391 (5)	151 (6)
C10—H10A···O1ⁱ	0.97	2.36	3.300 (5)	163
C11—H11A···Br1ⁱⁱ	0.96	2.84	3.726 (5)	154

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

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Dibromido{2,4-dichloro-6-[3-(dimethyl­ammonio)propyl­imino­meth­yl]phenolato}zinc(II)

Supporting information

Key indicators

checkCIF/PLATON results

Dibromido{2,4-dichloro-6-[3-(dimethylammonio)propyliminomethyl]phenolato}zinc(II)