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In the title mononuclear Schiff base zinc(II) complex, [ZnBr2(C12H17BrN2O)], the ZnII ion is four-coordinated by one O atom and one imine N atom of a Schiff base ligand, and by two Br atoms, giving a tetra­hedral geometry. The crystal structure is stabilized by inter­molecular C—H...O hydrogen bonds.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806019738/ac2025sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806019738/ac2025Isup2.hkl
Contains datablock I

CCDC reference: 610681

Key indicators

  • Single-crystal X-ray study
  • T = 298 K
  • Mean [sigma](C-C) = 0.013 Å
  • R factor = 0.072
  • wR factor = 0.215
  • Data-to-parameter ratio = 19.9

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Br3 - Zn1 .. 34.66 su PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C10 PLAT432_ALERT_2_B Short Inter X...Y Contact O1 .. C10 .. 2.88 Ang.
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.90 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 2.89 Ratio PLAT222_ALERT_3_C Large Non-Solvent H Ueq(max)/Ueq(min) ... 3.28 Ratio PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for N2 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for Zn1 PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 13 PLAT420_ALERT_2_C D-H Without Acceptor N2 - H2A ... ? PLAT420_ALERT_2_C D-H Without Acceptor N2 - H2B ... ?
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 0.905 Tmax scaled 0.469 Tmin scaled 0.390
0 ALERT level A = In general: serious problem 3 ALERT level B = Potentially serious problem 10 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 8 ALERT type 2 Indicator that the structure model may be wrong or deficient 4 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); 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.

Dibromo{4-bromo-2-[2-(isopropylamino)ethyliminomethyl]phenolato}zinc(II) top
Crystal data top
[ZnBr2(C12H17BrN2O)]F(000) = 984
Mr = 510.38Dx = 1.978 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
a = 7.044 (1) ÅCell parameters from 3471 reflections
b = 15.048 (3) Åθ = 2.5–24.1°
c = 16.179 (3) ŵ = 8.42 mm1
β = 92.007 (3)°T = 298 K
V = 1713.9 (5) Å3Block, colourless
Z = 40.12 × 0.10 × 0.09 mm
Data collection top
Bruker SMART CCD area-detector
diffractometer
3471 independent reflections
Radiation source: fine-focus sealed tube2078 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.075
ω scansθmax = 26.5°, θmin = 2.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 88
Tmin = 0.431, Tmax = 0.518k = 1818
13301 measured reflectionsl = 1920
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.072Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.215H-atom parameters constrained
S = 1.05 w = 1/[σ2(Fo2) + (0.1122P)2 + 0.0647P]
where P = (Fo2 + 2Fc2)/3
3471 reflections(Δ/σ)max < 0.001
174 parametersΔρmax = 0.96 e Å3
0 restraintsΔρmin = 1.86 e Å3
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
xyzUiso*/Ueq
Zn10.25285 (15)0.75608 (7)0.11034 (6)0.0423 (3)
Br10.96561 (16)0.50596 (7)0.34194 (7)0.0591 (4)
Br20.08996 (16)0.88974 (8)0.08763 (7)0.0605 (4)
Br30.1238 (2)0.63055 (12)0.03592 (12)0.1021 (6)
O10.3113 (9)0.7391 (5)0.2276 (4)0.0503 (17)
N10.5261 (11)0.7639 (5)0.0798 (4)0.0373 (17)
N20.6233 (14)0.6740 (7)0.0823 (5)0.065 (3)
H2A0.74720.68070.06820.078*
H2B0.57390.63370.04800.078*
C10.6198 (12)0.6794 (6)0.2021 (5)0.0354 (19)
C20.4594 (12)0.6908 (6)0.2513 (5)0.0362 (19)
C30.4646 (14)0.6473 (7)0.3284 (6)0.049 (2)
H30.36210.65460.36240.059*
C40.6095 (14)0.5958 (6)0.3553 (6)0.043 (2)
H40.60770.56940.40730.052*
C50.7633 (13)0.5822 (6)0.3044 (5)0.041 (2)
C60.7725 (13)0.6244 (6)0.2311 (5)0.040 (2)
H60.87900.61760.19930.048*
C70.6530 (13)0.7261 (6)0.1256 (5)0.038 (2)
H70.77750.72860.10840.046*
C80.5845 (13)0.8099 (6)0.0040 (5)0.042 (2)
H8A0.72180.81510.00530.050*
H8B0.53180.86940.00320.050*
C90.5210 (13)0.7625 (6)0.0732 (5)0.040 (2)
H9A0.54550.79970.12060.049*
H9B0.38520.75210.07230.049*
C100.6029 (14)0.6412 (6)0.1701 (5)0.041 (2)
H100.65990.68480.20680.049*
C110.3994 (18)0.6275 (8)0.1970 (7)0.066 (3)
H11A0.39180.61460.25520.099*
H11B0.32820.68030.18620.099*
H11C0.34800.57860.16700.099*
C120.711 (3)0.5550 (9)0.1752 (9)0.101 (5)
H12A0.70310.52360.12380.151*
H12B0.84150.56730.18580.151*
H12C0.65660.51940.21920.151*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0337 (6)0.0534 (7)0.0401 (6)0.0027 (5)0.0062 (4)0.0014 (5)
Br10.0615 (7)0.0521 (7)0.0636 (7)0.0165 (5)0.0017 (5)0.0092 (5)
Br20.0612 (7)0.0585 (7)0.0617 (7)0.0133 (5)0.0014 (5)0.0009 (5)
Br30.0864 (11)0.1016 (13)0.1182 (14)0.0129 (9)0.0040 (9)0.0023 (10)
O10.044 (4)0.068 (5)0.040 (3)0.014 (3)0.014 (3)0.002 (3)
N10.047 (4)0.037 (4)0.029 (4)0.001 (3)0.008 (3)0.001 (3)
N20.071 (6)0.077 (7)0.046 (5)0.019 (5)0.001 (4)0.002 (5)
C10.038 (5)0.038 (5)0.030 (4)0.003 (4)0.008 (4)0.005 (4)
C20.030 (4)0.045 (5)0.034 (4)0.005 (4)0.009 (3)0.000 (4)
C30.044 (5)0.063 (7)0.041 (5)0.011 (5)0.016 (4)0.011 (5)
C40.053 (6)0.043 (5)0.035 (5)0.007 (4)0.004 (4)0.004 (4)
C50.042 (5)0.039 (5)0.043 (5)0.001 (4)0.001 (4)0.000 (4)
C60.040 (5)0.044 (5)0.036 (5)0.001 (4)0.011 (4)0.001 (4)
C70.032 (5)0.046 (5)0.037 (5)0.001 (4)0.010 (4)0.007 (4)
C80.046 (5)0.043 (5)0.037 (5)0.000 (4)0.008 (4)0.004 (4)
C90.033 (5)0.051 (6)0.037 (5)0.004 (4)0.002 (4)0.006 (4)
C100.059 (6)0.038 (5)0.026 (4)0.002 (4)0.011 (4)0.002 (4)
C110.072 (8)0.075 (8)0.050 (6)0.014 (6)0.001 (6)0.003 (5)
C120.165 (16)0.068 (9)0.071 (9)0.052 (10)0.021 (9)0.005 (7)
Geometric parameters (Å, º) top
Zn1—O11.944 (7)C4—H40.9300
Zn1—N12.007 (8)C5—C61.349 (12)
Zn1—Br22.3382 (16)C6—H60.9300
Zn1—Br32.402 (2)C7—H70.9300
Br1—C51.912 (9)C8—C91.493 (12)
O1—C21.317 (10)C8—H8A0.9700
N1—C71.275 (12)C8—H8B0.9700
N1—C81.479 (11)C9—H9A0.9700
N2—C101.506 (12)C9—H9B0.9700
N2—C91.524 (13)C10—C111.498 (16)
N2—H2A0.9000C10—C121.507 (15)
N2—H2B0.9000C10—H100.9800
C1—C21.415 (11)C11—H11A0.9600
C1—C61.424 (13)C11—H11B0.9600
C1—C71.449 (12)C11—H11C0.9600
C2—C31.407 (12)C12—H12A0.9600
C3—C41.342 (14)C12—H12B0.9600
C3—H30.9300C12—H12C0.9600
C4—C51.399 (13)
O1—Zn1—N194.3 (3)N1—C7—C1125.5 (8)
O1—Zn1—Br2110.6 (2)N1—C7—H7117.2
N1—Zn1—Br2112.4 (2)C1—C7—H7117.2
O1—Zn1—Br3116.7 (2)N1—C8—C9112.8 (8)
N1—Zn1—Br3105.8 (2)N1—C8—H8A109.0
Br2—Zn1—Br3115.01 (7)C9—C8—H8A109.0
C2—O1—Zn1119.7 (5)N1—C8—H8B109.0
C7—N1—C8118.7 (7)C9—C8—H8B109.0
C7—N1—Zn1119.3 (6)H8A—C8—H8B107.8
C8—N1—Zn1121.9 (6)C8—C9—N2111.7 (8)
C10—N2—C9110.3 (7)C8—C9—H9A109.3
C10—N2—H2A109.6N2—C9—H9A109.3
C9—N2—H2A109.6C8—C9—H9B109.3
C10—N2—H2B109.6N2—C9—H9B109.3
C9—N2—H2B109.6H9A—C9—H9B107.9
H2A—N2—H2B108.1C11—C10—N2112.2 (8)
C2—C1—C6119.6 (8)C11—C10—C12110.1 (11)
C2—C1—C7125.3 (8)N2—C10—C12107.6 (9)
C6—C1—C7114.8 (7)C11—C10—H10109.0
O1—C2—C3120.7 (7)N2—C10—H10109.0
O1—C2—C1122.8 (8)C12—C10—H10109.0
C3—C2—C1116.5 (8)C10—C11—H11A109.5
C4—C3—C2123.5 (8)C10—C11—H11B109.5
C4—C3—H3118.2H11A—C11—H11B109.5
C2—C3—H3118.2C10—C11—H11C109.5
C3—C4—C5119.2 (8)H11A—C11—H11C109.5
C3—C4—H4120.4H11B—C11—H11C109.5
C5—C4—H4120.4C10—C12—H12A109.5
C6—C5—C4120.7 (9)C10—C12—H12B109.5
C6—C5—Br1120.3 (7)H12A—C12—H12B109.5
C4—C5—Br1118.9 (7)C10—C12—H12C109.5
C5—C6—C1120.3 (8)H12A—C12—H12C109.5
C5—C6—H6119.8H12B—C12—H12C109.5
C1—C6—H6119.8
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10···O1i0.981.912.882 (11)170
Symmetry code: (i) x+1/2, y+3/2, z1/2.
 

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