In the mononuclear title complex, [Zn(C10H9BrNO)2], the ZnII atom is four-coordinated by two imine N and two phenolate O atoms from two Schiff base ligands in a distorted tetrahedral geometry.
Supporting information
CCDC reference: 293866
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.007 Å
- R factor = 0.043
- wR factor = 0.102
- Data-to-parameter ratio = 18.9
checkCIF/PLATON results
No syntax errors found
Alert level A
PLAT220_ALERT_2_A Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.70 Ratio
| Author Response: This is probably caused by the tensile force of the cyclopropyl
ring.
|
Alert level B
PLAT222_ALERT_3_B Large Non-Solvent H Ueq(max)/Ueq(min) ... 4.29 Ratio
PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C19
PLAT241_ALERT_2_B Check High Ueq as Compared to Neighbors for C20
PLAT242_ALERT_2_B Check Low Ueq as Compared to Neighbors for C18
Alert level C
ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR) is > 1.10
Tmin and Tmax reported: 0.346 0.538
Tmin and Tmax expected: 0.302 0.538
RR = 1.147
Please check that your absorption correction is appropriate.
PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large ....... 1.15
PLAT213_ALERT_2_C Atom C19 has ADP max/min Ratio ............. 3.20 prolat
PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C9
PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C8
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 7
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
7 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
0 ALERT type 4 Improvement, methodology, query or suggestion
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.
Bis[4-bromo-2-(cyclopropyliminomethyl)phenolato]zinc(II)
top
Crystal data top
[Zn(C10H9BrNO)2] | F(000) = 2144 |
Mr = 543.55 | Dx = 1.779 Mg m−3 |
Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 4849 reflections |
a = 23.260 (2) Å | θ = 2.3–23.6° |
b = 13.305 (2) Å | µ = 5.16 mm−1 |
c = 13.119 (3) Å | T = 298 K |
V = 4060.0 (12) Å3 | Block, colourless |
Z = 8 | 0.24 × 0.20 × 0.12 mm |
Data collection top
Bruker SMART CCD area-detector diffractometer | 4619 independent reflections |
Radiation source: fine-focus sealed tube | 2693 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.065 |
ω scans | θmax = 27.5°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −29→28 |
Tmin = 0.346, Tmax = 0.538 | k = −16→17 |
21839 measured reflections | l = −16→16 |
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) = 0.102 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0401P)2 + 2.1967P] where P = (Fo2 + 2Fc2)/3 |
4619 reflections | (Δ/σ)max = 0.001 |
244 parameters | Δρmax = 0.55 e Å−3 |
0 restraints | Δρmin = −0.78 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 | 0.76037 (2) | 0.13990 (3) | 0.33956 (4) | 0.03721 (14) | |
Br1 | 0.51249 (2) | −0.10138 (4) | 0.10635 (5) | 0.0729 (2) | |
Br2 | 0.98190 (3) | 0.41105 (5) | 0.62473 (4) | 0.0797 (2) | |
O1 | 0.69883 (12) | 0.1778 (2) | 0.2504 (2) | 0.0451 (7) | |
O2 | 0.83049 (12) | 0.2094 (2) | 0.3144 (2) | 0.0455 (8) | |
N1 | 0.75946 (13) | −0.0070 (2) | 0.3064 (2) | 0.0366 (8) | |
N2 | 0.74880 (14) | 0.1859 (3) | 0.4843 (2) | 0.0406 (9) | |
C1 | 0.66665 (15) | 0.0079 (3) | 0.2194 (3) | 0.0315 (9) | |
C2 | 0.65917 (17) | 0.1142 (3) | 0.2201 (3) | 0.0363 (10) | |
C3 | 0.60622 (18) | 0.1511 (3) | 0.1862 (3) | 0.0439 (11) | |
H3 | 0.6000 | 0.2201 | 0.1866 | 0.053* | |
C4 | 0.56289 (18) | 0.0888 (4) | 0.1522 (3) | 0.0467 (11) | |
H4 | 0.5280 | 0.1156 | 0.1309 | 0.056* | |
C5 | 0.57194 (17) | −0.0138 (3) | 0.1503 (3) | 0.0421 (10) | |
C6 | 0.62259 (16) | −0.0534 (3) | 0.1827 (3) | 0.0381 (10) | |
H6 | 0.6280 | −0.1226 | 0.1804 | 0.046* | |
C7 | 0.71656 (16) | −0.0441 (3) | 0.2572 (3) | 0.0344 (9) | |
H7 | 0.7180 | −0.1128 | 0.2446 | 0.041* | |
C8 | 0.80398 (19) | −0.0748 (3) | 0.3382 (3) | 0.0506 (12) | |
H8 | 0.7965 | −0.1462 | 0.3256 | 0.061* | |
C9 | 0.8646 (2) | −0.0430 (5) | 0.3295 (5) | 0.087 (2) | |
H9A | 0.8927 | −0.0934 | 0.3101 | 0.105* | |
H9B | 0.8722 | 0.0240 | 0.3036 | 0.105* | |
C10 | 0.8380 (3) | −0.0517 (4) | 0.4305 (5) | 0.0842 (19) | |
H10A | 0.8292 | 0.0099 | 0.4668 | 0.101* | |
H10B | 0.8497 | −0.1075 | 0.4733 | 0.101* | |
C11 | 0.84267 (17) | 0.2690 (3) | 0.4872 (3) | 0.0345 (10) | |
C12 | 0.86212 (18) | 0.2509 (3) | 0.3863 (3) | 0.0384 (10) | |
C13 | 0.91874 (19) | 0.2805 (3) | 0.3622 (3) | 0.0447 (11) | |
H13 | 0.9331 | 0.2669 | 0.2975 | 0.054* | |
C14 | 0.95302 (19) | 0.3284 (3) | 0.4313 (4) | 0.0516 (12) | |
H14 | 0.9900 | 0.3480 | 0.4130 | 0.062* | |
C15 | 0.93305 (19) | 0.3477 (3) | 0.5280 (4) | 0.0477 (12) | |
C16 | 0.87939 (18) | 0.3185 (3) | 0.5561 (3) | 0.0423 (10) | |
H16 | 0.8667 | 0.3314 | 0.6221 | 0.051* | |
C17 | 0.78764 (18) | 0.2398 (3) | 0.5272 (3) | 0.0397 (10) | |
H17 | 0.7791 | 0.2629 | 0.5924 | 0.048* | |
C18 | 0.6980 (2) | 0.1634 (4) | 0.5433 (3) | 0.0584 (14) | |
H18 | 0.6954 | 0.1962 | 0.6101 | 0.070* | |
C19 | 0.6734 (4) | 0.0622 (6) | 0.5364 (7) | 0.147 (4) | |
H19A | 0.6921 | 0.0143 | 0.4915 | 0.176* | |
H19B | 0.6571 | 0.0333 | 0.5978 | 0.176* | |
C20 | 0.6431 (3) | 0.1469 (8) | 0.4895 (5) | 0.135 (4) | |
H20A | 0.6082 | 0.1704 | 0.5221 | 0.162* | |
H20B | 0.6432 | 0.1514 | 0.4157 | 0.162* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.0462 (3) | 0.0354 (3) | 0.0301 (3) | −0.0062 (2) | −0.0045 (2) | −0.0029 (2) |
Br1 | 0.0444 (3) | 0.0832 (4) | 0.0912 (5) | −0.0143 (3) | −0.0187 (3) | −0.0090 (3) |
Br2 | 0.0779 (4) | 0.0970 (5) | 0.0641 (4) | −0.0389 (3) | −0.0266 (3) | −0.0034 (3) |
O1 | 0.0579 (18) | 0.0338 (16) | 0.0435 (19) | −0.0032 (14) | −0.0127 (15) | 0.0019 (14) |
O2 | 0.0556 (18) | 0.0536 (19) | 0.0274 (17) | −0.0166 (15) | 0.0024 (14) | −0.0075 (14) |
N1 | 0.0393 (18) | 0.0364 (19) | 0.034 (2) | 0.0025 (16) | −0.0068 (16) | −0.0019 (15) |
N2 | 0.048 (2) | 0.042 (2) | 0.033 (2) | −0.0089 (17) | 0.0003 (16) | −0.0025 (16) |
C1 | 0.039 (2) | 0.030 (2) | 0.025 (2) | −0.0019 (18) | −0.0018 (17) | −0.0034 (18) |
C2 | 0.046 (2) | 0.042 (3) | 0.021 (2) | 0.000 (2) | −0.0016 (18) | −0.0042 (19) |
C3 | 0.051 (3) | 0.040 (3) | 0.041 (3) | 0.012 (2) | −0.003 (2) | −0.001 (2) |
C4 | 0.039 (2) | 0.067 (3) | 0.035 (3) | 0.013 (2) | −0.0021 (19) | −0.001 (2) |
C5 | 0.036 (2) | 0.053 (3) | 0.037 (3) | −0.006 (2) | 0.0007 (19) | −0.005 (2) |
C6 | 0.039 (2) | 0.042 (3) | 0.032 (2) | −0.001 (2) | 0.0012 (19) | −0.0030 (19) |
C7 | 0.043 (2) | 0.028 (2) | 0.033 (2) | 0.0005 (18) | −0.0018 (19) | −0.0045 (18) |
C8 | 0.054 (3) | 0.039 (3) | 0.059 (3) | 0.007 (2) | −0.018 (2) | −0.002 (2) |
C9 | 0.048 (3) | 0.094 (5) | 0.120 (6) | 0.010 (3) | −0.036 (4) | −0.005 (4) |
C10 | 0.101 (5) | 0.080 (4) | 0.072 (4) | 0.029 (4) | −0.055 (4) | −0.014 (3) |
C11 | 0.045 (2) | 0.028 (2) | 0.030 (2) | −0.0035 (19) | −0.0070 (19) | 0.0010 (18) |
C12 | 0.047 (2) | 0.040 (2) | 0.029 (3) | −0.004 (2) | −0.0061 (19) | 0.005 (2) |
C13 | 0.050 (3) | 0.050 (3) | 0.034 (3) | −0.004 (2) | 0.001 (2) | 0.007 (2) |
C14 | 0.044 (3) | 0.054 (3) | 0.057 (3) | −0.013 (2) | −0.008 (2) | 0.004 (3) |
C15 | 0.052 (3) | 0.044 (3) | 0.047 (3) | −0.012 (2) | −0.017 (2) | 0.002 (2) |
C16 | 0.054 (3) | 0.038 (3) | 0.035 (3) | −0.004 (2) | −0.008 (2) | −0.001 (2) |
C17 | 0.050 (3) | 0.040 (3) | 0.029 (2) | −0.004 (2) | 0.001 (2) | −0.004 (2) |
C18 | 0.065 (3) | 0.075 (4) | 0.035 (3) | −0.026 (3) | 0.018 (2) | −0.026 (2) |
C19 | 0.182 (10) | 0.116 (6) | 0.143 (8) | −0.110 (6) | 0.105 (7) | −0.072 (6) |
C20 | 0.062 (4) | 0.281 (12) | 0.063 (5) | −0.077 (6) | 0.020 (3) | −0.061 (6) |
Geometric parameters (Å, º) top
Zn1—O2 | 1.904 (3) | C8—H8 | 0.98 |
Zn1—O1 | 1.916 (3) | C9—C10 | 1.467 (8) |
Zn1—N1 | 2.002 (3) | C9—H9A | 0.97 |
Zn1—N2 | 2.013 (3) | C9—H9B | 0.97 |
Br1—C5 | 1.898 (4) | C10—H10A | 0.97 |
Br2—C15 | 1.900 (4) | C10—H10B | 0.97 |
O1—C2 | 1.313 (4) | C11—C16 | 1.408 (5) |
O2—C12 | 1.317 (4) | C11—C12 | 1.419 (5) |
N1—C7 | 1.286 (4) | C11—C17 | 1.437 (5) |
N1—C8 | 1.435 (5) | C12—C13 | 1.410 (6) |
N2—C17 | 1.284 (5) | C13—C14 | 1.365 (6) |
N2—C18 | 1.443 (5) | C13—H13 | 0.93 |
C1—C6 | 1.396 (5) | C14—C15 | 1.375 (6) |
C1—C2 | 1.425 (5) | C14—H14 | 0.93 |
C1—C7 | 1.439 (5) | C15—C16 | 1.358 (6) |
C2—C3 | 1.398 (5) | C16—H16 | 0.93 |
C3—C4 | 1.379 (6) | C17—H17 | 0.93 |
C3—H3 | 0.93 | C18—C19 | 1.467 (7) |
C4—C5 | 1.381 (6) | C18—C20 | 1.477 (8) |
C4—H4 | 0.93 | C18—H18 | 0.98 |
C5—C6 | 1.359 (5) | C19—C20 | 1.465 (11) |
C6—H6 | 0.93 | C19—H19A | 0.97 |
C7—H7 | 0.93 | C19—H19B | 0.97 |
C8—C9 | 1.476 (7) | C20—H20A | 0.97 |
C8—C10 | 1.479 (6) | C20—H20B | 0.97 |
| | | |
O2—Zn1—O1 | 113.95 (12) | H9A—C9—H9B | 114.9 |
O2—Zn1—N1 | 116.46 (13) | C9—C10—C8 | 60.1 (3) |
O1—Zn1—N1 | 96.69 (12) | C9—C10—H10A | 117.8 |
O2—Zn1—N2 | 97.50 (12) | C8—C10—H10A | 117.8 |
O1—Zn1—N2 | 113.33 (13) | C9—C10—H10B | 117.8 |
N1—Zn1—N2 | 120.01 (14) | C8—C10—H10B | 117.8 |
C2—O1—Zn1 | 122.7 (3) | H10A—C10—H10B | 114.9 |
C12—O2—Zn1 | 123.9 (2) | C16—C11—C12 | 119.0 (4) |
C7—N1—C8 | 117.7 (3) | C16—C11—C17 | 115.6 (4) |
C7—N1—Zn1 | 119.4 (3) | C12—C11—C17 | 125.4 (4) |
C8—N1—Zn1 | 122.9 (3) | O2—C12—C13 | 118.6 (4) |
C17—N2—C18 | 117.1 (4) | O2—C12—C11 | 124.1 (4) |
C17—N2—Zn1 | 119.3 (3) | C13—C12—C11 | 117.3 (4) |
C18—N2—Zn1 | 123.5 (3) | C14—C13—C12 | 121.8 (4) |
C6—C1—C2 | 119.5 (4) | C14—C13—H13 | 119.1 |
C6—C1—C7 | 115.5 (3) | C12—C13—H13 | 119.1 |
C2—C1—C7 | 125.0 (3) | C13—C14—C15 | 120.2 (4) |
O1—C2—C3 | 119.3 (4) | C13—C14—H14 | 119.9 |
O1—C2—C1 | 123.7 (4) | C15—C14—H14 | 119.9 |
C3—C2—C1 | 117.0 (4) | C16—C15—C14 | 120.5 (4) |
C4—C3—C2 | 122.4 (4) | C16—C15—Br2 | 119.6 (4) |
C4—C3—H3 | 118.8 | C14—C15—Br2 | 119.8 (3) |
C2—C3—H3 | 118.8 | C15—C16—C11 | 121.1 (4) |
C3—C4—C5 | 119.2 (4) | C15—C16—H16 | 119.4 |
C3—C4—H4 | 120.4 | C11—C16—H16 | 119.4 |
C5—C4—H4 | 120.4 | N2—C17—C11 | 128.1 (4) |
C6—C5—C4 | 120.7 (4) | N2—C17—H17 | 115.9 |
C6—C5—Br1 | 119.2 (3) | C11—C17—H17 | 115.9 |
C4—C5—Br1 | 120.1 (3) | N2—C18—C19 | 118.5 (5) |
C5—C6—C1 | 121.2 (4) | N2—C18—C20 | 118.8 (4) |
C5—C6—H6 | 119.4 | C19—C18—C20 | 59.7 (5) |
C1—C6—H6 | 119.4 | N2—C18—H18 | 116.0 |
N1—C7—C1 | 127.9 (4) | C19—C18—H18 | 116.0 |
N1—C7—H7 | 116.1 | C20—C18—H18 | 116.0 |
C1—C7—H7 | 116.1 | C20—C19—C18 | 60.5 (4) |
N1—C8—C9 | 119.1 (4) | C20—C19—H19A | 117.7 |
N1—C8—C10 | 119.6 (4) | C18—C19—H19A | 117.7 |
C9—C8—C10 | 59.5 (3) | C20—C19—H19B | 117.7 |
N1—C8—H8 | 115.7 | C18—C19—H19B | 117.7 |
C9—C8—H8 | 115.7 | H19A—C19—H19B | 114.8 |
C10—C8—H8 | 115.7 | C19—C20—C18 | 59.8 (5) |
C10—C9—C8 | 60.3 (3) | C19—C20—H20A | 117.8 |
C10—C9—H9A | 117.7 | C18—C20—H20A | 117.8 |
C8—C9—H9A | 117.7 | C19—C20—H20B | 117.8 |
C10—C9—H9B | 117.7 | C18—C20—H20B | 117.8 |
C8—C9—H9B | 117.7 | H20A—C20—H20B | 114.9 |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C8—H8···O1i | 0.98 | 2.54 | 3.488 (5) | 162 |
C18—H18···O1ii | 0.98 | 2.49 | 3.442 (5) | 163 |
C20—H20B···O1 | 0.97 | 2.55 | 3.419 (7) | 149 |
Symmetry codes: (i) −x+3/2, y−1/2, z; (ii) x, −y+1/2, z+1/2. |