{4-Bromo-2-[3-(dimethyl­amino)propyl­imino­meth­yl]phenolato}dichloro­zinc(II)

The title compound, [ZnCl₂(C₁₂H₁₇BrN₂O)], is a mononuclear Schiff base zinc(II) complex. The Zn atom is tetra­hedrally coordinated by one phenolate O atom and one imine N atom of the Schiff base, and by two chloride anions. In the crystal structure, mol­ecules are linked through inter­molecular N—H...O and C—H...Cl inter­actions, forming layers parallel to the bc plane.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.010 Å
• R factor = 0.050
• wR factor = 0.139
• Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT027_ALERT_3_A _diffrn_reflns_theta_full (too) Low ............      23.51 Deg.

Author Response: This is probably caused by the poor diffraction quality of the crystal.

Alert level B
THETM01_ALERT_3_B  The value of sine(theta_max)/wavelength is less than 0.575
            Calculated sin(theta_max)/wavelength =    0.5613
PLAT023_ALERT_3_B Resolution (too) Low [sin(th)/Lambda < 0.6].....      23.51 Deg.
PLAT222_ALERT_3_B Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       4.30 Ratio
PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X)  Zn1    -   Cl1     ..      17.33 su

Alert level C
PLAT062_ALERT_4_C Rescale T(min) & T(max) by .....................       0.95
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       3.11 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        Zn1
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 ...       0.02 AngSq
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...         10

   1 ALERT level A = In general: serious problem
   4 ALERT level B = Potentially serious problem
   6 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
   5 ALERT type 2 Indicator that the structure model may be wrong or deficient
   5 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: SAINT (Bruker, 1998); 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: SHELXTL.

{4-Bromo-2-[3-(dimethylamino)propyliminomethyl]phenolato}dichlorozinc(II)

Crystal data

[ZnCl2(C12H17BrN2O)]	F(000) = 840
Mr = 421.46	Dx = 1.673 Mg m^−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 3889 reflections
a = 6.938 (1) Å	θ = 2.5–27.4°
b = 15.202 (1) Å	µ = 4.17 mm^−1
c = 15.906 (1) Å	T = 298 K
β = 94.058 (1)°	Block, colourless
V = 1673.4 (3) Å^3	0.18 × 0.17 × 0.12 mm
Z = 4

Data collection

Buker SMART APEX 1000 CCD area-detector diffractometer	2457 independent reflections
Radiation source: fine-focus sealed tube	1682 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
ω scans	θmax = 23.5°, θmin = 2.7°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→7
Tmin = 0.521, Tmax = 0.635	k = −9→17
7159 measured reflections	l = −17→17

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.139	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ^2(Fo^2) + (0.0627P)^2 + 2.2538P] where P = (Fo^2 + 2Fc^2)/3
2457 reflections	(Δ/σ)max < 0.001
178 parameters	Δρmax = 0.96 e Å^−3
1 restraint	Δρmin = −0.80 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	0.24115 (11)	0.25674 (6)	0.61210 (5)	0.0441 (3)
Br1	0.97259 (12)	0.00326 (6)	0.85112 (5)	0.0583 (3)
Cl1	0.1097 (4)	0.1397 (2)	0.5454 (2)	0.1077 (10)
Cl2	0.0840 (3)	0.38193 (15)	0.59217 (14)	0.0631 (6)
O1	0.3032 (7)	0.2366 (3)	0.7331 (3)	0.0480 (13)
N1	0.5177 (8)	0.2628 (4)	0.5834 (3)	0.0370 (14)
N2	0.6089 (11)	0.1385 (5)	0.3324 (4)	0.0559 (18)
C1	0.6202 (9)	0.1775 (5)	0.7083 (4)	0.0370 (17)
C2	0.4551 (10)	0.1869 (5)	0.7570 (4)	0.0403 (17)
C3	0.4592 (10)	0.1429 (5)	0.8333 (4)	0.0470 (19)
H3	0.3563	0.1504	0.8671	0.056*
C4	0.6090 (10)	0.0884 (5)	0.8616 (5)	0.0466 (19)
H4	0.6056	0.0588	0.9126	0.056*
C5	0.7644 (10)	0.0789 (5)	0.8125 (4)	0.0451 (19)
C6	0.7708 (10)	0.1227 (5)	0.7393 (4)	0.0438 (18)
H6	0.8788	0.1165	0.7084	0.053*
C7	0.6471 (10)	0.2247 (5)	0.6306 (4)	0.0385 (17)
H7	0.7726	0.2273	0.6137	0.046*
C8	0.5764 (10)	0.3072 (5)	0.5076 (4)	0.0416 (18)
H8A	0.7159	0.3134	0.5114	0.050*
H8B	0.5208	0.3658	0.5048	0.050*
C9	0.5137 (9)	0.2579 (5)	0.4277 (4)	0.0411 (18)
H9A	0.3766	0.2451	0.4271	0.049*
H9B	0.5347	0.2945	0.3793	0.049*
C10	0.6232 (11)	0.1739 (5)	0.4212 (4)	0.050 (2)
H10A	0.5725	0.1305	0.4586	0.061*
H10B	0.7579	0.1838	0.4392	0.061*
C11	0.4049 (14)	0.1223 (7)	0.2997 (5)	0.080 (3)
H11A	0.4032	0.1001	0.2431	0.119*
H11B	0.3336	0.1764	0.3000	0.119*
H11C	0.3469	0.0800	0.3349	0.119*
C12	0.726 (2)	0.0565 (7)	0.3261 (7)	0.114 (5)
H12A	0.6771	0.0120	0.3618	0.172*
H12B	0.8583	0.0687	0.3437	0.172*
H12C	0.7170	0.0362	0.2688	0.172*
H2	0.653 (9)	0.182 (3)	0.300 (3)	0.04 (2)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Zn1	0.0371 (5)	0.0553 (6)	0.0404 (5)	0.0042 (4)	0.0050 (4)	−0.0010 (5)
Br1	0.0617 (5)	0.0530 (6)	0.0599 (5)	0.0136 (4)	0.0018 (4)	0.0083 (4)
Cl1	0.0822 (17)	0.103 (2)	0.135 (3)	−0.0236 (17)	−0.0135 (17)	0.009 (2)
Cl2	0.0617 (13)	0.0583 (14)	0.0684 (14)	0.0141 (11)	−0.0009 (10)	−0.0013 (12)
O1	0.044 (3)	0.062 (3)	0.039 (3)	0.014 (3)	0.010 (2)	0.006 (3)
N1	0.037 (3)	0.043 (4)	0.031 (3)	−0.001 (3)	0.004 (3)	0.001 (3)
N2	0.087 (5)	0.044 (4)	0.039 (4)	0.005 (4)	0.019 (4)	0.001 (3)
C1	0.034 (4)	0.041 (4)	0.037 (4)	−0.001 (3)	0.011 (3)	−0.005 (3)
C2	0.042 (4)	0.039 (4)	0.039 (4)	−0.001 (4)	0.000 (3)	0.001 (4)
C3	0.042 (4)	0.060 (5)	0.039 (4)	−0.002 (4)	0.011 (3)	0.000 (4)
C4	0.054 (5)	0.046 (5)	0.040 (4)	−0.006 (4)	0.006 (4)	0.004 (4)
C5	0.046 (4)	0.048 (5)	0.040 (4)	0.003 (4)	0.002 (4)	−0.005 (4)
C6	0.037 (4)	0.057 (5)	0.039 (4)	−0.002 (4)	0.012 (3)	0.001 (4)
C7	0.033 (4)	0.052 (5)	0.031 (4)	−0.005 (3)	0.009 (3)	−0.006 (4)
C8	0.047 (4)	0.049 (5)	0.030 (4)	−0.004 (4)	0.013 (3)	−0.005 (3)
C9	0.039 (4)	0.054 (5)	0.032 (4)	0.005 (4)	0.008 (3)	0.008 (4)
C10	0.058 (5)	0.058 (5)	0.035 (4)	0.009 (4)	0.006 (4)	0.000 (4)
C11	0.091 (7)	0.091 (8)	0.056 (6)	−0.031 (6)	−0.006 (5)	−0.007 (5)
C12	0.202 (14)	0.073 (7)	0.072 (7)	0.062 (8)	0.032 (8)	−0.012 (6)

Geometric parameters (Å, º)

Zn1—O1	1.967 (5)	C4—H4	0.9300
Zn1—N1	2.006 (5)	C5—C6	1.344 (9)
Zn1—Cl2	2.205 (2)	C6—H6	0.9300
Zn1—Cl1	2.233 (3)	C7—H7	0.9300
Br1—C5	1.914 (7)	C8—C9	1.513 (9)
O1—C2	1.330 (8)	C8—H8A	0.9700
N1—C7	1.270 (8)	C8—H8B	0.9700
N1—C8	1.464 (8)	C9—C10	1.493 (10)
N2—C11	1.493 (11)	C9—H9A	0.9700
N2—C12	1.494 (11)	C9—H9B	0.9700
N2—C10	1.508 (9)	C10—H10A	0.9700
N2—H2	0.91 (5)	C10—H10B	0.9700
C1—C6	1.398 (10)	C11—H11A	0.9600
C1—C2	1.434 (9)	C11—H11B	0.9600
C1—C7	1.452 (9)	C11—H11C	0.9600
C2—C3	1.385 (10)	C12—H12A	0.9600
C3—C4	1.379 (10)	C12—H12B	0.9600
C3—H3	0.9300	C12—H12C	0.9600
C4—C5	1.384 (10)
O1—Zn1—N1	94.8 (2)	N1—C7—C1	126.9 (6)
O1—Zn1—Cl2	110.32 (16)	N1—C7—H7	116.5
N1—Zn1—Cl2	113.49 (18)	C1—C7—H7	116.5
O1—Zn1—Cl1	113.23 (18)	N1—C8—C9	112.5 (6)
N1—Zn1—Cl1	107.09 (18)	N1—C8—H8A	109.1
Cl2—Zn1—Cl1	115.99 (10)	C9—C8—H8A	109.1
C2—O1—Zn1	118.8 (4)	N1—C8—H8B	109.1
C7—N1—C8	118.1 (6)	C9—C8—H8B	109.1
C7—N1—Zn1	119.5 (5)	H8A—C8—H8B	107.8
C8—N1—Zn1	122.4 (4)	C10—C9—C8	111.4 (6)
C11—N2—C12	110.1 (8)	C10—C9—H9A	109.3
C11—N2—C10	112.5 (6)	C8—C9—H9A	109.3
C12—N2—C10	111.1 (7)	C10—C9—H9B	109.3
C11—N2—H2	106 (4)	C8—C9—H9B	109.3
C12—N2—H2	111 (4)	H9A—C9—H9B	108.0
C10—N2—H2	106 (4)	C9—C10—N2	111.7 (6)
C6—C1—C2	118.3 (6)	C9—C10—H10A	109.3
C6—C1—C7	117.2 (6)	N2—C10—H10A	109.3
C2—C1—C7	124.5 (6)	C9—C10—H10B	109.3
O1—C2—C3	119.4 (6)	N2—C10—H10B	109.3
O1—C2—C1	123.3 (6)	H10A—C10—H10B	107.9
C3—C2—C1	117.2 (7)	N2—C11—H11A	109.5
C4—C3—C2	123.0 (7)	N2—C11—H11B	109.5
C4—C3—H3	118.5	H11A—C11—H11B	109.5
C2—C3—H3	118.5	N2—C11—H11C	109.5
C3—C4—C5	118.5 (7)	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	120.8 (7)	N2—C12—H12B	109.5
C6—C5—Br1	120.4 (5)	H12A—C12—H12B	109.5
C4—C5—Br1	118.8 (6)	N2—C12—H12C	109.5
C5—C6—C1	122.1 (6)	H12A—C12—H12C	109.5
C5—C6—H6	119.0	H12B—C12—H12C	109.5
C1—C6—H6	119.0

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1^i	0.91 (5)	1.98 (5)	2.867 (8)	168 (6)
C11—H11A···Cl2^i	0.96	2.80	3.609 (8)	142 (6)

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