Dibromido{4-chloro-2-[3-(dimethyl­amino)propyl­imino­meth­yl]phenolato}zinc(II)

The title compound, [ZnBr₂(C₁₂H₁₇ClN₂O)], 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 Br anions, forming a tetra­hedral geometry. In the crystal structure, mol­ecules are linked through inter­molecular N—H...O hydrogen bonds, forming chains running along the c axis.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.011 Å
• R factor = 0.060
• wR factor = 0.179
• Data-to-parameter ratio = 19.6

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Br2    -   Zn1     ..      18.78 su

Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.92
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.88 Ratio
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.55 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for         N2
PLAT245_ALERT_2_C U(iso) H2      Smaller than U(eq) N2      by ...       0.01 AngSq
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         11

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      0.919
            Tmax scaled      0.499 Tmin scaled      0.349

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   6 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
   4 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 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, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 2002); software used to prepare material for publication: SHELXTL.

Dibromido{4-chloro-2-[3-(dimethylamino)propyliminomethyl]phenolato}zinc(II)

Crystal data

[ZnBr2(C12H17ClN2O)]	F(000) = 912
Mr = 465.92	Dx = 1.828 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1555 reflections
a = 7.103 (1) Å	θ = 2.5–24.9°
b = 14.851 (2) Å	µ = 6.32 mm^−1
c = 16.058 (2) Å	T = 298 K
β = 91.886 (2)°	Block, colourless
V = 1693.0 (4) Å^3	0.19 × 0.11 × 0.11 mm
Z = 4

Data collection

Bruker APEXII area-detector diffractometer	3481 independent reflections
Radiation source: fine-focus sealed tube	2178 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.065
ω scans	θmax = 26.5°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −8→8
Tmin = 0.380, Tmax = 0.543	k = −18→18
12802 measured reflections	l = −20→20

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.179	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0779P)^2 + 5.4115P] where P = (Fo^2 + 2Fc^2)/3
3481 reflections	(Δ/σ)max < 0.001
178 parameters	Δρmax = 0.66 e Å^−3
1 restraint	Δρmin = −1.21 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	0.73282 (12)	0.74314 (6)	0.89473 (5)	0.0419 (3)
Br1	0.89523 (14)	0.60775 (7)	0.91491 (6)	0.0627 (3)
Br2	0.86093 (16)	0.86927 (8)	0.96877 (7)	0.0754 (4)
Cl1	0.0431 (3)	0.99137 (17)	0.66569 (15)	0.0652 (7)
O1	0.6791 (7)	0.7639 (4)	0.7763 (3)	0.0488 (14)
N1	0.4592 (8)	0.7318 (4)	0.9220 (4)	0.0368 (14)
N2	0.3792 (11)	0.8561 (5)	1.1716 (4)	0.0510 (18)
C1	0.3667 (9)	0.8206 (5)	0.8017 (4)	0.0331 (16)
C2	0.5303 (10)	0.8131 (5)	0.7535 (4)	0.0379 (17)
C3	0.5270 (11)	0.8577 (6)	0.6772 (5)	0.048 (2)
H3	0.6294	0.8509	0.6432	0.058*
C4	0.3808 (12)	0.9111 (6)	0.6499 (5)	0.047 (2)
H4	0.3841	0.9395	0.5984	0.056*
C5	0.2291 (11)	0.9220 (5)	0.6996 (5)	0.0400 (18)
C6	0.2183 (10)	0.8745 (5)	0.7728 (5)	0.0417 (19)
H6	0.1099	0.8784	0.8036	0.050*
C7	0.3358 (11)	0.7707 (6)	0.8774 (5)	0.0413 (18)
H7	0.2124	0.7671	0.8947	0.050*
C8	0.4021 (11)	0.6822 (6)	0.9963 (5)	0.0439 (19)
H8A	0.4575	0.6225	0.9960	0.053*
H8B	0.2662	0.6754	0.9946	0.053*
C9	0.4632 (10)	0.7303 (5)	1.0761 (5)	0.0409 (18)
H9A	0.4377	0.6920	1.1234	0.049*
H9B	0.5979	0.7410	1.0759	0.049*
C10	0.3622 (12)	0.8188 (6)	1.0855 (5)	0.049 (2)
H10A	0.4131	0.8621	1.0470	0.059*
H10B	0.2299	0.8106	1.0705	0.059*
C11	0.2718 (18)	0.9395 (8)	1.1792 (7)	0.094 (4)
H11A	0.3074	0.9809	1.1366	0.142*
H11B	0.2978	0.9657	1.2330	0.142*
H11C	0.1397	0.9266	1.1730	0.142*
C12	0.5799 (16)	0.8701 (8)	1.2007 (6)	0.081 (3)
H12A	0.6440	0.9055	1.1603	0.121*
H12B	0.6412	0.8128	1.2071	0.121*
H12C	0.5829	0.9010	1.2532	0.121*
H2	0.308 (9)	0.821 (4)	1.203 (4)	0.04 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0327 (5)	0.0589 (6)	0.0344 (5)	0.0040 (4)	0.0042 (4)	−0.0012 (4)
Br1	0.0628 (6)	0.0655 (6)	0.0594 (6)	0.0162 (5)	−0.0044 (5)	−0.0043 (5)
Br2	0.0678 (7)	0.0785 (8)	0.0799 (8)	−0.0102 (5)	0.0023 (6)	−0.0036 (6)
Cl1	0.0664 (15)	0.0631 (15)	0.0661 (15)	0.0235 (12)	0.0007 (12)	0.0105 (12)
O1	0.039 (3)	0.075 (4)	0.032 (3)	0.016 (3)	0.008 (2)	0.003 (3)
N1	0.037 (3)	0.045 (4)	0.029 (3)	−0.005 (3)	0.009 (3)	−0.006 (3)
N2	0.064 (5)	0.056 (4)	0.034 (4)	0.004 (4)	0.014 (3)	0.005 (3)
C1	0.033 (4)	0.039 (4)	0.027 (4)	−0.002 (3)	0.004 (3)	−0.002 (3)
C2	0.042 (4)	0.044 (4)	0.028 (4)	0.001 (3)	0.001 (3)	−0.006 (3)
C3	0.039 (4)	0.069 (6)	0.037 (4)	0.006 (4)	0.009 (3)	0.002 (4)
C4	0.055 (5)	0.051 (5)	0.034 (4)	−0.012 (4)	0.005 (4)	0.001 (4)
C5	0.044 (5)	0.041 (4)	0.034 (4)	−0.004 (3)	−0.009 (3)	−0.003 (3)
C6	0.037 (4)	0.047 (5)	0.042 (4)	−0.002 (3)	0.015 (4)	−0.005 (4)
C7	0.033 (4)	0.060 (5)	0.032 (4)	0.001 (4)	0.006 (3)	−0.001 (4)
C8	0.041 (4)	0.054 (5)	0.037 (4)	0.001 (4)	0.007 (3)	0.006 (4)
C9	0.034 (4)	0.054 (5)	0.035 (4)	0.002 (3)	0.007 (3)	0.004 (4)
C10	0.050 (5)	0.062 (6)	0.034 (4)	0.014 (4)	0.004 (4)	0.012 (4)
C11	0.128 (11)	0.079 (8)	0.078 (8)	0.042 (7)	0.023 (7)	−0.010 (6)
C12	0.091 (8)	0.099 (9)	0.052 (6)	−0.030 (7)	−0.003 (6)	−0.008 (6)

Geometric parameters (Å, º)

Zn1—O1	1.952 (5)	C4—H4	0.9300
Zn1—N1	2.014 (6)	C5—C6	1.376 (11)
Zn1—Br1	2.3354 (14)	C6—H6	0.9300
Zn1—Br2	2.3830 (15)	C7—H7	0.9300
Cl1—C5	1.748 (8)	C8—C9	1.517 (11)
O1—C2	1.327 (9)	C8—H8A	0.9700
N1—C7	1.254 (10)	C8—H8B	0.9700
N1—C8	1.471 (9)	C9—C10	1.509 (11)
N2—C11	1.462 (12)	C9—H9A	0.9700
N2—C10	1.491 (10)	C9—H9B	0.9700
N2—C12	1.499 (12)	C10—H10A	0.9700
N2—H2	0.89 (6)	C10—H10B	0.9700
C1—C6	1.391 (10)	C11—H11A	0.9600
C1—C2	1.421 (9)	C11—H11B	0.9600
C1—C7	1.447 (10)	C11—H11C	0.9600
C2—C3	1.392 (10)	C12—H12A	0.9600
C3—C4	1.367 (12)	C12—H12B	0.9600
C3—H3	0.9300	C12—H12C	0.9600
C4—C5	1.372 (11)
O1—Zn1—N1	93.8 (2)	N1—C7—C1	126.4 (7)
O1—Zn1—Br1	110.53 (17)	N1—C7—H7	116.8
N1—Zn1—Br1	111.95 (18)	C1—C7—H7	116.8
O1—Zn1—Br2	114.92 (19)	N1—C8—C9	111.8 (6)
N1—Zn1—Br2	108.23 (17)	N1—C8—H8A	109.3
Br1—Zn1—Br2	115.39 (5)	C9—C8—H8A	109.3
C2—O1—Zn1	118.9 (4)	N1—C8—H8B	109.3
C7—N1—C8	119.2 (6)	C9—C8—H8B	109.3
C7—N1—Zn1	119.9 (5)	H8A—C8—H8B	107.9
C8—N1—Zn1	120.8 (5)	C10—C9—C8	111.8 (7)
C11—N2—C10	111.4 (7)	C10—C9—H9A	109.3
C11—N2—C12	110.5 (9)	C8—C9—H9A	109.3
C10—N2—C12	112.8 (7)	C10—C9—H9B	109.3
C11—N2—H2	98 (5)	C8—C9—H9B	109.3
C10—N2—H2	106 (5)	H9A—C9—H9B	107.9
C12—N2—H2	117 (5)	N2—C10—C9	113.1 (6)
C6—C1—C2	119.3 (6)	N2—C10—H10A	109.0
C6—C1—C7	116.1 (6)	C9—C10—H10A	109.0
C2—C1—C7	124.5 (7)	N2—C10—H10B	109.0
O1—C2—C3	119.6 (6)	C9—C10—H10B	109.0
O1—C2—C1	123.5 (6)	H10A—C10—H10B	107.8
C3—C2—C1	116.8 (7)	N2—C11—H11A	109.5
C4—C3—C2	123.3 (7)	N2—C11—H11B	109.5
C4—C3—H3	118.4	H11A—C11—H11B	109.5
C2—C3—H3	118.4	N2—C11—H11C	109.5
C3—C4—C5	119.0 (7)	H11A—C11—H11C	109.5
C3—C4—H4	120.5	H11B—C11—H11C	109.5
C5—C4—H4	120.5	N2—C12—H12A	109.5
C4—C5—C6	120.2 (7)	N2—C12—H12B	109.5
C4—C5—Cl1	119.2 (6)	H12A—C12—H12B	109.5
C6—C5—Cl1	120.4 (6)	N2—C12—H12C	109.5
C5—C6—C1	121.1 (7)	H12A—C12—H12C	109.5
C5—C6—H6	119.5	H12B—C12—H12C	109.5
C1—C6—H6	119.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1^i	0.89 (6)	1.97 (6)	2.859 (9)	174 (7)

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