The title compound, [ZnBr
2(C
13H
19ClN
2O)], 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 bromide anions in a tetrahedral geometry. In the crystal structure, molecules are linked through intermolecular N—H
O and C—H
Br hydrogen bonds, forming layers parallel to the
bc plane.
Supporting information
CCDC reference: 640357
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.006 Å
- R factor = 0.043
- wR factor = 0.113
- Data-to-parameter ratio = 21.4
checkCIF/PLATON results
No syntax errors found
Alert level C
CELLV02_ALERT_1_C The supplied cell volume s.u. differs from that
calculated from the cell parameter s.u.'s by > 2
Calculated cell volume su = 2.92
Cell volume su given = 6.00
PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.77
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ?
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X) Br2 - Zn1 .. 8.98 su
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 0.769
Tmax scaled 0.276 Tmin scaled 0.256
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
5 ALERT level C = Check and explain
1 ALERT level G = General alerts; check
2 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
1 ALERT type 4 Improvement, methodology, query or suggestion
0 ALERT type 5 Informative message, check
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.
Dibromo{4-chloro-2-[(2-diethylaminoethylimino)methyl]phenolato}zinc(II)
top
Crystal data top
[ZnBr2(C13H19ClN2O)] | F(000) = 944 |
Mr = 479.94 | Dx = 1.823 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 2913 reflections |
a = 14.921 (1) Å | θ = 2.6–25.7° |
b = 8.9624 (1) Å | µ = 6.12 mm−1 |
c = 13.092 (2) Å | T = 298 K |
β = 92.600 (1)° | Block, colourless |
V = 1749.0 (6) Å3 | 0.23 × 0.21 × 0.21 mm |
Z = 4 | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 4008 independent reflections |
Radiation source: fine-focus sealed tube | 2754 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.039 |
ω scans | θmax = 27.5°, θmin = 2.7° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −17→19 |
Tmin = 0.333, Tmax = 0.360 | k = −9→11 |
10219 measured reflections | l = −17→13 |
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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.113 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.00 | w = 1/[σ2(Fo2) + (0.0591P)2] where P = (Fo2 + 2Fc2)/3 |
4008 reflections | (Δ/σ)max < 0.001 |
187 parameters | Δρmax = 0.89 e Å−3 |
1 restraint | Δρmin = −0.67 e Å−3 |
Special details top
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 (Å2) top | x | y | z | Uiso*/Ueq | |
Zn1 | 0.22962 (3) | 0.23841 (5) | −0.08799 (3) | 0.03693 (15) | |
Br1 | 0.24699 (4) | 0.44459 (5) | −0.19705 (4) | 0.06443 (19) | |
Br2 | 0.07924 (4) | 0.18373 (6) | −0.05244 (4) | 0.06643 (19) | |
Cl1 | 0.51403 (10) | −0.33621 (13) | 0.13599 (10) | 0.0644 (4) | |
O1 | 0.28871 (19) | 0.0540 (3) | −0.12930 (19) | 0.0370 (7) | |
N1 | 0.3032 (2) | 0.2648 (3) | 0.0440 (2) | 0.0330 (7) | |
N2 | 0.1832 (2) | 0.5518 (3) | 0.1994 (2) | 0.0330 (7) | |
C1 | 0.3717 (3) | 0.0181 (4) | 0.0320 (3) | 0.0301 (8) | |
C2 | 0.3414 (3) | −0.0274 (4) | −0.0673 (3) | 0.0311 (8) | |
C3 | 0.3680 (3) | −0.1692 (4) | −0.0999 (3) | 0.0393 (10) | |
H3 | 0.3500 | −0.2009 | −0.1653 | 0.047* | |
C4 | 0.4196 (3) | −0.2627 (4) | −0.0387 (3) | 0.0420 (10) | |
H4 | 0.4361 | −0.3559 | −0.0628 | 0.050* | |
C5 | 0.4471 (3) | −0.2182 (4) | 0.0587 (3) | 0.0405 (10) | |
C6 | 0.4254 (3) | −0.0804 (4) | 0.0934 (3) | 0.0352 (9) | |
H6 | 0.4460 | −0.0505 | 0.1583 | 0.042* | |
C7 | 0.3547 (3) | 0.1612 (4) | 0.0789 (3) | 0.0325 (8) | |
H7 | 0.3848 | 0.1797 | 0.1414 | 0.039* | |
C8 | 0.2966 (3) | 0.4013 (4) | 0.1050 (3) | 0.0386 (9) | |
H8A | 0.3174 | 0.4863 | 0.0670 | 0.046* | |
H8B | 0.3333 | 0.3925 | 0.1678 | 0.046* | |
C9 | 0.1987 (3) | 0.4224 (4) | 0.1294 (3) | 0.0351 (9) | |
H9A | 0.1637 | 0.4374 | 0.0660 | 0.042* | |
H9B | 0.1773 | 0.3320 | 0.1609 | 0.042* | |
C10 | 0.2195 (3) | 0.6981 (4) | 0.1604 (3) | 0.0406 (10) | |
H10A | 0.2103 | 0.7752 | 0.2109 | 0.049* | |
H10B | 0.2836 | 0.6882 | 0.1530 | 0.049* | |
C11 | 0.1764 (4) | 0.7467 (5) | 0.0598 (4) | 0.0593 (13) | |
H11A | 0.1824 | 0.6689 | 0.0101 | 0.089* | |
H11B | 0.2054 | 0.8355 | 0.0369 | 0.089* | |
H11C | 0.1140 | 0.7668 | 0.0681 | 0.089* | |
C12 | 0.0857 (3) | 0.5592 (4) | 0.2221 (3) | 0.0429 (10) | |
H12A | 0.0669 | 0.4625 | 0.2466 | 0.051* | |
H12B | 0.0512 | 0.5802 | 0.1592 | 0.051* | |
C13 | 0.0647 (4) | 0.6762 (6) | 0.3005 (4) | 0.0689 (15) | |
H13A | 0.1026 | 0.6617 | 0.3609 | 0.103* | |
H13B | 0.0030 | 0.6676 | 0.3175 | 0.103* | |
H13C | 0.0751 | 0.7735 | 0.2729 | 0.103* | |
H2 | 0.216 (2) | 0.529 (4) | 0.2572 (19) | 0.035 (11)* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.0493 (3) | 0.0314 (2) | 0.0295 (2) | 0.00799 (19) | −0.0044 (2) | −0.00309 (18) |
Br1 | 0.1017 (5) | 0.0405 (3) | 0.0513 (3) | 0.0169 (2) | 0.0062 (3) | 0.0144 (2) |
Br2 | 0.0464 (3) | 0.0854 (4) | 0.0673 (3) | −0.0053 (3) | 0.0012 (2) | −0.0276 (3) |
Cl1 | 0.0789 (10) | 0.0502 (7) | 0.0624 (8) | 0.0257 (6) | −0.0168 (7) | 0.0073 (6) |
O1 | 0.0523 (19) | 0.0307 (13) | 0.0273 (13) | 0.0088 (12) | −0.0062 (12) | −0.0052 (10) |
N1 | 0.043 (2) | 0.0278 (16) | 0.0285 (15) | 0.0025 (13) | −0.0018 (14) | −0.0047 (12) |
N2 | 0.045 (2) | 0.0274 (15) | 0.0256 (15) | 0.0017 (13) | −0.0039 (14) | −0.0034 (12) |
C1 | 0.031 (2) | 0.0302 (18) | 0.0294 (18) | 0.0021 (15) | 0.0025 (15) | −0.0013 (14) |
C2 | 0.035 (2) | 0.0276 (19) | 0.0305 (19) | 0.0008 (15) | 0.0027 (16) | −0.0011 (15) |
C3 | 0.046 (3) | 0.037 (2) | 0.034 (2) | 0.0075 (18) | −0.0022 (18) | −0.0070 (17) |
C4 | 0.047 (3) | 0.029 (2) | 0.050 (2) | 0.0075 (17) | 0.000 (2) | −0.0067 (17) |
C5 | 0.043 (3) | 0.032 (2) | 0.046 (2) | 0.0071 (17) | −0.0035 (19) | 0.0094 (17) |
C6 | 0.036 (2) | 0.039 (2) | 0.0310 (19) | 0.0025 (16) | −0.0025 (16) | 0.0006 (16) |
C7 | 0.034 (2) | 0.037 (2) | 0.0263 (18) | −0.0048 (16) | 0.0000 (15) | −0.0037 (15) |
C8 | 0.052 (3) | 0.0297 (19) | 0.034 (2) | 0.0008 (17) | −0.0032 (18) | −0.0066 (16) |
C9 | 0.050 (3) | 0.0247 (18) | 0.0301 (19) | −0.0002 (16) | −0.0018 (17) | −0.0071 (14) |
C10 | 0.049 (3) | 0.0239 (18) | 0.049 (2) | −0.0031 (16) | 0.002 (2) | −0.0028 (16) |
C11 | 0.059 (4) | 0.053 (3) | 0.066 (3) | −0.002 (2) | 0.004 (3) | 0.028 (2) |
C12 | 0.052 (3) | 0.041 (2) | 0.036 (2) | −0.0006 (19) | 0.0072 (19) | 0.0003 (17) |
C13 | 0.086 (4) | 0.064 (3) | 0.059 (3) | 0.014 (3) | 0.026 (3) | −0.010 (3) |
Geometric parameters (Å, º) top
Zn1—O1 | 1.961 (2) | C5—C6 | 1.360 (5) |
Zn1—N1 | 2.018 (3) | C6—H6 | 0.9300 |
Zn1—Br1 | 2.3567 (7) | C7—H7 | 0.9300 |
Zn1—Br2 | 2.3636 (9) | C8—C9 | 1.520 (6) |
Cl1—C5 | 1.746 (4) | C8—H8A | 0.9700 |
O1—C2 | 1.323 (4) | C8—H8B | 0.9700 |
N1—C7 | 1.277 (5) | C9—H9A | 0.9700 |
N1—C8 | 1.466 (4) | C9—H9B | 0.9700 |
N2—C12 | 1.500 (6) | C10—C11 | 1.504 (6) |
N2—C9 | 1.503 (4) | C10—H10A | 0.9700 |
N2—C10 | 1.516 (5) | C10—H10B | 0.9700 |
N2—H2 | 0.91 (3) | C11—H11A | 0.9600 |
C1—C2 | 1.417 (5) | C11—H11B | 0.9600 |
C1—C6 | 1.417 (5) | C11—H11C | 0.9600 |
C1—C7 | 1.449 (5) | C12—C13 | 1.510 (6) |
C2—C3 | 1.404 (5) | C12—H12A | 0.9700 |
C3—C4 | 1.372 (5) | C12—H12B | 0.9700 |
C3—H3 | 0.9300 | C13—H13A | 0.9600 |
C4—C5 | 1.380 (6) | C13—H13B | 0.9600 |
C4—H4 | 0.9300 | C13—H13C | 0.9600 |
| | | |
O1—Zn1—N1 | 95.81 (11) | N1—C8—C9 | 107.9 (3) |
O1—Zn1—Br1 | 115.51 (9) | N1—C8—H8A | 110.1 |
N1—Zn1—Br1 | 110.86 (9) | C9—C8—H8A | 110.1 |
O1—Zn1—Br2 | 108.80 (9) | N1—C8—H8B | 110.1 |
N1—Zn1—Br2 | 109.88 (10) | C9—C8—H8B | 110.1 |
Br1—Zn1—Br2 | 114.41 (3) | H8A—C8—H8B | 108.4 |
C2—O1—Zn1 | 123.9 (2) | N2—C9—C8 | 113.6 (3) |
C7—N1—C8 | 117.8 (3) | N2—C9—H9A | 108.9 |
C7—N1—Zn1 | 121.1 (2) | C8—C9—H9A | 108.9 |
C8—N1—Zn1 | 121.1 (2) | N2—C9—H9B | 108.9 |
C12—N2—C9 | 109.4 (3) | C8—C9—H9B | 108.9 |
C12—N2—C10 | 113.1 (3) | H9A—C9—H9B | 107.7 |
C9—N2—C10 | 113.3 (3) | C11—C10—N2 | 113.7 (3) |
C12—N2—H2 | 110 (3) | C11—C10—H10A | 108.8 |
C9—N2—H2 | 104 (2) | N2—C10—H10A | 108.8 |
C10—N2—H2 | 107 (2) | C11—C10—H10B | 108.8 |
C2—C1—C6 | 119.3 (3) | N2—C10—H10B | 108.8 |
C2—C1—C7 | 126.0 (3) | H10A—C10—H10B | 107.7 |
C6—C1—C7 | 114.6 (3) | C10—C11—H11A | 109.5 |
O1—C2—C3 | 118.7 (3) | C10—C11—H11B | 109.5 |
O1—C2—C1 | 124.1 (3) | H11A—C11—H11B | 109.5 |
C3—C2—C1 | 117.2 (3) | C10—C11—H11C | 109.5 |
C4—C3—C2 | 122.3 (4) | H11A—C11—H11C | 109.5 |
C4—C3—H3 | 118.8 | H11B—C11—H11C | 109.5 |
C2—C3—H3 | 118.8 | N2—C12—C13 | 113.5 (4) |
C3—C4—C5 | 119.9 (3) | N2—C12—H12A | 108.9 |
C3—C4—H4 | 120.0 | C13—C12—H12A | 108.9 |
C5—C4—H4 | 120.0 | N2—C12—H12B | 108.9 |
C6—C5—C4 | 120.4 (3) | C13—C12—H12B | 108.9 |
C6—C5—Cl1 | 119.7 (3) | H12A—C12—H12B | 107.7 |
C4—C5—Cl1 | 119.9 (3) | C12—C13—H13A | 109.5 |
C5—C6—C1 | 120.9 (3) | C12—C13—H13B | 109.5 |
C5—C6—H6 | 119.6 | H13A—C13—H13B | 109.5 |
C1—C6—H6 | 119.6 | C12—C13—H13C | 109.5 |
N1—C7—C1 | 127.3 (3) | H13A—C13—H13C | 109.5 |
N1—C7—H7 | 116.3 | H13B—C13—H13C | 109.5 |
C1—C7—H7 | 116.3 | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O1i | 0.91 (3) | 1.95 (3) | 2.843 (4) | 170 (3) |
C10—H10A···Br1ii | 0.97 | 2.83 | 3.719 (4) | 153 |
C11—H11C···Br2iii | 0.96 | 2.91 | 3.862 (4) | 169 |
Symmetry codes: (i) x, −y+1/2, z+1/2; (ii) x, −y+3/2, z+1/2; (iii) −x, −y+1, −z. |