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The title compound, [ZnBr
2(C
12H
16Cl
2N
2O)], 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.
Supporting information
CCDC reference: 646723
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
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 |
Mr = 500.36 | Dx = 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 | Rint = 0.069 |
ω scans | θmax = 27.5°, θmin = 1.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −10→10 |
Tmin = 0.222, Tmax = 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(Fo2) + (0.0315P)2 + 13.4509P] where P = (Fo2 + 2Fc2)/3 |
4017 reflections | (Δ/σ)max < 0.001 |
186 parameters | Δρmax = 1.64 e Å−3 |
1 restraint | Δρmin = −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 | Uiso*/Ueq | |
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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