Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807023136/fj2029sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807023136/fj2029Isup2.hkl |
CCDC reference: 650696
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.005 Å
- R factor = 0.037
- wR factor = 0.086
- Data-to-parameter ratio = 18.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT431_ALERT_2_C Short Inter HL..A Contact Br2 .. O2 .. 3.32 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact Br4 .. O1 .. 3.24 Ang.
Alert level G PLAT794_ALERT_5_G Check Predicted Bond Valency for Zn1 (2) 2.04
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
3,5-Dibromo-2-hydroxybenzaldehyde (1.0 mmol, 280.0 mg), cyclopropylamine (1.0 mmol, 57.0 mg) and zinc dichloride (0.5 mmol, 68.1 mg) were dissolved in a methanol solution (50 ml). The mixture was stirred at room temperature for 30 min and filtered. After keeping the filtrate in air for 8 days, colorless block-shaped crystals were formed.
H atoms were placed in idealized positions and constrained to ride on their parent atoms, with C—H = 0.93–0.97 Å and Uiso(H) = 1.2 times Ueq(C). The maximum residual electron density peak is observed 1.91 Å from Br3. The minimum residual electron density peak is observed 0.86 Å from Br1.
Recently, we have reported the structure of a Schiff base copper(II) complex (Yuan & Zhang, 2005). As an extension of our investigations in this area, we report here the title compound, a new mononuclear Schiff base zinc(II) complex, (I).
In (I), the Zn atom is four-coordinated by two N and two O atoms from two Schiff base ligands, forming a tetrahedral coordination (Fig. 1). The bond lengths and angles are comparable to the values observed in the similar Schiff base zinc(II) complexes (You, 2005a,b).
For related literature, see: You (2005a, 2005b); Yuan & Zhang (2005).
Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); 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, 1997); software used to prepare material for publication: SHELXTL.
Fig. 1. The structure of (I). Displacement ellipsoids are drawn at the 30% probability level. |
[Zn(C10H8Br2NO)2] | Z = 2 |
Mr = 701.36 | F(000) = 672 |
Triclinic, P1 | Dx = 2.122 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.5490 (15) Å | Cell parameters from 3389 reflections |
b = 9.883 (2) Å | θ = 2.2–26.0° |
c = 15.814 (3) Å | µ = 8.42 mm−1 |
α = 78.34 (3)° | T = 298 K |
β = 82.49 (2)° | Block, colorless |
γ = 72.24 (3)° | 0.21 × 0.20 × 0.20 mm |
V = 1097.4 (4) Å3 |
Bruker SMART 1000 CCD area detector diffractometer | 4962 independent reflections |
Radiation source: fine-focus sealed tube | 3772 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
ω scans | θmax = 27.5°, θmin = 1.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −9→9 |
Tmin = 0.182, Tmax = 0.187 | k = −12→12 |
12652 measured reflections | l = −20→20 |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.086 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0384P)2 + 0.0662P] where P = (Fo2 + 2Fc2)/3 |
4962 reflections | (Δ/σ)max < 0.001 |
262 parameters | Δρmax = 0.65 e Å−3 |
0 restraints | Δρmin = −0.73 e Å−3 |
[Zn(C10H8Br2NO)2] | γ = 72.24 (3)° |
Mr = 701.36 | V = 1097.4 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 7.5490 (15) Å | Mo Kα radiation |
b = 9.883 (2) Å | µ = 8.42 mm−1 |
c = 15.814 (3) Å | T = 298 K |
α = 78.34 (3)° | 0.21 × 0.20 × 0.20 mm |
β = 82.49 (2)° |
Bruker SMART 1000 CCD area detector diffractometer | 4962 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3772 reflections with I > 2σ(I) |
Tmin = 0.182, Tmax = 0.187 | Rint = 0.031 |
12652 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.086 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.65 e Å−3 |
4962 reflections | Δρmin = −0.73 e Å−3 |
262 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Zn1 | 0.63891 (6) | 0.71541 (4) | 0.74530 (2) | 0.03400 (12) | |
Br1 | 0.26207 (8) | 0.94742 (6) | 0.97427 (3) | 0.07098 (18) | |
Br2 | 0.68209 (6) | 0.50762 (5) | 1.21708 (2) | 0.05179 (13) | |
Br3 | 0.27136 (7) | 0.65425 (6) | 0.53715 (3) | 0.05651 (14) | |
Br4 | 0.68691 (6) | 0.92573 (4) | 0.27077 (2) | 0.04488 (12) | |
O1 | 0.5050 (4) | 0.7705 (3) | 0.84927 (15) | 0.0408 (6) | |
O2 | 0.5105 (3) | 0.7210 (3) | 0.64830 (14) | 0.0390 (6) | |
N1 | 0.7902 (4) | 0.5186 (3) | 0.80191 (18) | 0.0315 (7) | |
N2 | 0.7973 (4) | 0.8430 (3) | 0.68016 (18) | 0.0346 (7) | |
C1 | 0.6930 (5) | 0.5771 (4) | 0.9477 (2) | 0.0305 (8) | |
C2 | 0.5521 (5) | 0.7084 (4) | 0.9267 (2) | 0.0313 (8) | |
C3 | 0.4576 (5) | 0.7739 (4) | 0.9983 (2) | 0.0383 (9) | |
C4 | 0.4982 (5) | 0.7182 (4) | 1.0822 (2) | 0.0395 (9) | |
H4 | 0.4330 | 0.7660 | 1.1268 | 0.047* | |
C5 | 0.6371 (5) | 0.5904 (4) | 1.1000 (2) | 0.0367 (9) | |
C6 | 0.7302 (5) | 0.5184 (4) | 1.0352 (2) | 0.0366 (9) | |
H6 | 0.8191 | 0.4298 | 1.0485 | 0.044* | |
C7 | 0.7958 (5) | 0.4884 (4) | 0.8844 (2) | 0.0354 (8) | |
H7 | 0.8751 | 0.3992 | 0.9063 | 0.042* | |
C8 | 0.9041 (5) | 0.4100 (4) | 0.7528 (2) | 0.0381 (9) | |
H8 | 0.9931 | 0.3281 | 0.7853 | 0.046* | |
C9 | 0.9640 (6) | 0.4547 (4) | 0.6611 (2) | 0.0478 (11) | |
H9A | 0.9240 | 0.5566 | 0.6368 | 0.057* | |
H9B | 1.0871 | 0.4028 | 0.6393 | 0.057* | |
C10 | 0.8206 (6) | 0.3770 (5) | 0.6822 (3) | 0.0512 (11) | |
H10A | 0.8559 | 0.2776 | 0.6735 | 0.061* | |
H10B | 0.6928 | 0.4314 | 0.6709 | 0.061* | |
C11 | 0.6953 (5) | 0.8382 (4) | 0.5393 (2) | 0.0306 (8) | |
C12 | 0.5560 (5) | 0.7659 (4) | 0.5682 (2) | 0.0313 (8) | |
C13 | 0.4627 (5) | 0.7448 (4) | 0.5020 (2) | 0.0353 (8) | |
C14 | 0.5031 (5) | 0.7891 (4) | 0.4152 (2) | 0.0355 (8) | |
H14 | 0.4384 | 0.7728 | 0.3739 | 0.043* | |
C15 | 0.6398 (5) | 0.8575 (4) | 0.3902 (2) | 0.0344 (8) | |
C16 | 0.7330 (5) | 0.8838 (4) | 0.4509 (2) | 0.0344 (8) | |
H16 | 0.8226 | 0.9328 | 0.4332 | 0.041* | |
C17 | 0.7993 (5) | 0.8760 (4) | 0.5980 (2) | 0.0361 (8) | |
H17 | 0.8776 | 0.9316 | 0.5719 | 0.043* | |
C18 | 0.9148 (6) | 0.8962 (4) | 0.7221 (2) | 0.0419 (9) | |
H18 | 1.0079 | 0.9340 | 0.6837 | 0.050* | |
C19 | 0.9688 (7) | 0.8296 (5) | 0.8106 (3) | 0.0531 (11) | |
H19A | 0.9238 | 0.7485 | 0.8390 | 0.064* | |
H19B | 1.0926 | 0.8241 | 0.8242 | 0.064* | |
C20 | 0.8322 (7) | 0.9723 (5) | 0.7968 (3) | 0.0592 (12) | |
H20A | 0.8720 | 1.0547 | 0.8017 | 0.071* | |
H20B | 0.7031 | 0.9790 | 0.8165 | 0.071* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.0398 (3) | 0.0374 (2) | 0.0239 (2) | −0.01177 (19) | −0.00172 (17) | −0.00263 (17) |
Br1 | 0.0755 (4) | 0.0668 (3) | 0.0449 (3) | 0.0230 (3) | −0.0076 (2) | −0.0167 (2) |
Br2 | 0.0531 (3) | 0.0735 (3) | 0.0269 (2) | −0.0183 (2) | −0.00901 (17) | −0.00014 (19) |
Br3 | 0.0553 (3) | 0.0854 (4) | 0.0435 (2) | −0.0439 (3) | −0.0016 (2) | −0.0088 (2) |
Br4 | 0.0519 (3) | 0.0523 (3) | 0.02541 (19) | −0.0129 (2) | −0.00125 (16) | 0.00065 (16) |
O1 | 0.0453 (16) | 0.0445 (16) | 0.0227 (12) | −0.0010 (13) | −0.0005 (11) | −0.0030 (11) |
O2 | 0.0416 (15) | 0.0552 (17) | 0.0236 (13) | −0.0246 (13) | −0.0013 (11) | 0.0014 (11) |
N1 | 0.0328 (17) | 0.0344 (16) | 0.0269 (15) | −0.0097 (13) | 0.0008 (12) | −0.0064 (12) |
N2 | 0.0398 (18) | 0.0368 (17) | 0.0291 (16) | −0.0136 (14) | −0.0036 (13) | −0.0052 (13) |
C1 | 0.0296 (19) | 0.0345 (19) | 0.0263 (17) | −0.0088 (15) | −0.0002 (14) | −0.0045 (14) |
C2 | 0.0309 (19) | 0.040 (2) | 0.0248 (17) | −0.0131 (16) | −0.0010 (14) | −0.0050 (15) |
C3 | 0.035 (2) | 0.040 (2) | 0.035 (2) | −0.0048 (17) | −0.0021 (16) | −0.0050 (16) |
C4 | 0.045 (2) | 0.053 (2) | 0.0255 (18) | −0.019 (2) | 0.0018 (16) | −0.0116 (17) |
C5 | 0.040 (2) | 0.050 (2) | 0.0258 (18) | −0.0207 (19) | −0.0097 (16) | −0.0008 (16) |
C6 | 0.038 (2) | 0.039 (2) | 0.033 (2) | −0.0118 (17) | −0.0072 (16) | −0.0022 (16) |
C7 | 0.035 (2) | 0.032 (2) | 0.037 (2) | −0.0090 (16) | −0.0040 (16) | −0.0038 (16) |
C8 | 0.038 (2) | 0.038 (2) | 0.037 (2) | −0.0055 (17) | −0.0017 (16) | −0.0115 (16) |
C9 | 0.054 (3) | 0.045 (2) | 0.041 (2) | −0.009 (2) | 0.0113 (19) | −0.0154 (18) |
C10 | 0.052 (3) | 0.056 (3) | 0.054 (3) | −0.015 (2) | −0.005 (2) | −0.027 (2) |
C11 | 0.031 (2) | 0.0312 (19) | 0.0289 (18) | −0.0081 (15) | −0.0053 (15) | −0.0036 (14) |
C12 | 0.032 (2) | 0.033 (2) | 0.0257 (17) | −0.0060 (16) | −0.0009 (14) | −0.0047 (15) |
C13 | 0.034 (2) | 0.037 (2) | 0.036 (2) | −0.0121 (17) | 0.0001 (16) | −0.0066 (16) |
C14 | 0.039 (2) | 0.039 (2) | 0.0295 (19) | −0.0097 (17) | −0.0057 (16) | −0.0087 (16) |
C15 | 0.035 (2) | 0.036 (2) | 0.0261 (18) | −0.0037 (16) | 0.0023 (15) | −0.0046 (15) |
C16 | 0.037 (2) | 0.034 (2) | 0.034 (2) | −0.0146 (17) | 0.0007 (16) | −0.0047 (16) |
C17 | 0.037 (2) | 0.040 (2) | 0.035 (2) | −0.0172 (17) | −0.0014 (16) | −0.0058 (16) |
C18 | 0.047 (2) | 0.051 (2) | 0.035 (2) | −0.024 (2) | −0.0004 (17) | −0.0103 (17) |
C19 | 0.064 (3) | 0.058 (3) | 0.047 (2) | −0.030 (2) | −0.021 (2) | −0.001 (2) |
C20 | 0.062 (3) | 0.065 (3) | 0.059 (3) | −0.018 (3) | −0.011 (2) | −0.028 (2) |
Zn1—O1 | 1.901 (2) | C8—C10 | 1.486 (5) |
Zn1—O2 | 1.902 (2) | C8—H8 | 0.9800 |
Zn1—N1 | 2.024 (3) | C9—C10 | 1.477 (6) |
Zn1—N2 | 2.038 (3) | C9—H9A | 0.9700 |
Br1—C3 | 1.898 (4) | C9—H9B | 0.9700 |
Br2—C5 | 1.897 (3) | C10—H10A | 0.9700 |
Br3—C13 | 1.890 (4) | C10—H10B | 0.9700 |
Br4—C15 | 1.898 (3) | C11—C16 | 1.399 (5) |
O1—C2 | 1.296 (4) | C11—C12 | 1.423 (5) |
O2—C12 | 1.293 (4) | C11—C17 | 1.459 (5) |
N1—C7 | 1.281 (4) | C12—C13 | 1.416 (5) |
N1—C8 | 1.447 (4) | C13—C14 | 1.378 (5) |
N2—C17 | 1.274 (4) | C14—C15 | 1.375 (5) |
N2—C18 | 1.443 (5) | C14—H14 | 0.9300 |
C1—C2 | 1.415 (5) | C15—C16 | 1.369 (5) |
C1—C6 | 1.416 (5) | C16—H16 | 0.9300 |
C1—C7 | 1.453 (5) | C17—H17 | 0.9300 |
C2—C3 | 1.419 (5) | C18—C19 | 1.473 (5) |
C3—C4 | 1.366 (5) | C18—C20 | 1.493 (5) |
C4—C5 | 1.378 (5) | C18—H18 | 0.9800 |
C4—H4 | 0.9300 | C19—C20 | 1.465 (6) |
C5—C6 | 1.360 (5) | C19—H19A | 0.9700 |
C6—H6 | 0.9300 | C19—H19B | 0.9700 |
C7—H7 | 0.9300 | C20—H20A | 0.9700 |
C8—C9 | 1.483 (5) | C20—H20B | 0.9700 |
O1—Zn1—O2 | 120.70 (11) | H9A—C9—H9B | 114.9 |
O1—Zn1—N1 | 95.56 (11) | C9—C10—C8 | 60.0 (3) |
O2—Zn1—N1 | 116.58 (12) | C9—C10—H10A | 117.8 |
O1—Zn1—N2 | 116.16 (12) | C8—C10—H10A | 117.8 |
O2—Zn1—N2 | 95.52 (11) | C9—C10—H10B | 117.8 |
N1—Zn1—N2 | 113.73 (12) | C8—C10—H10B | 117.8 |
C2—O1—Zn1 | 125.0 (2) | H10A—C10—H10B | 114.9 |
C12—O2—Zn1 | 126.1 (2) | C16—C11—C12 | 120.7 (3) |
C7—N1—C8 | 117.0 (3) | C16—C11—C17 | 116.0 (3) |
C7—N1—Zn1 | 120.1 (2) | C12—C11—C17 | 123.3 (3) |
C8—N1—Zn1 | 122.8 (2) | O2—C12—C13 | 119.5 (3) |
C17—N2—C18 | 116.9 (3) | O2—C12—C11 | 125.0 (3) |
C17—N2—Zn1 | 119.8 (3) | C13—C12—C11 | 115.4 (3) |
C18—N2—Zn1 | 123.3 (2) | C14—C13—C12 | 123.2 (3) |
C2—C1—C6 | 120.4 (3) | C14—C13—Br3 | 119.7 (3) |
C2—C1—C7 | 123.5 (3) | C12—C13—Br3 | 117.1 (3) |
C6—C1—C7 | 115.8 (3) | C15—C14—C13 | 119.5 (3) |
O1—C2—C1 | 125.5 (3) | C15—C14—H14 | 120.3 |
O1—C2—C3 | 119.2 (3) | C13—C14—H14 | 120.3 |
C1—C2—C3 | 115.2 (3) | C16—C15—C14 | 120.4 (3) |
C4—C3—C2 | 123.8 (3) | C16—C15—Br4 | 120.3 (3) |
C4—C3—Br1 | 119.1 (3) | C14—C15—Br4 | 119.2 (3) |
C2—C3—Br1 | 117.1 (3) | C15—C16—C11 | 120.9 (3) |
C3—C4—C5 | 119.2 (3) | C15—C16—H16 | 119.5 |
C3—C4—H4 | 120.4 | C11—C16—H16 | 119.5 |
C5—C4—H4 | 120.4 | N2—C17—C11 | 128.7 (3) |
C6—C5—C4 | 120.7 (3) | N2—C17—H17 | 115.7 |
C6—C5—Br2 | 120.2 (3) | C11—C17—H17 | 115.7 |
C4—C5—Br2 | 118.9 (3) | N2—C18—C19 | 120.8 (3) |
C5—C6—C1 | 120.6 (3) | N2—C18—C20 | 118.8 (4) |
C5—C6—H6 | 119.7 | C19—C18—C20 | 59.2 (3) |
C1—C6—H6 | 119.7 | N2—C18—H18 | 115.5 |
N1—C7—C1 | 127.7 (3) | C19—C18—H18 | 115.5 |
N1—C7—H7 | 116.1 | C20—C18—H18 | 115.5 |
C1—C7—H7 | 116.1 | C20—C19—C18 | 61.1 (3) |
N1—C8—C9 | 119.1 (3) | C20—C19—H19A | 117.7 |
N1—C8—C10 | 118.5 (3) | C18—C19—H19A | 117.7 |
C9—C8—C10 | 59.7 (3) | C20—C19—H19B | 117.7 |
N1—C8—H8 | 115.9 | C18—C19—H19B | 117.7 |
C9—C8—H8 | 115.9 | H19A—C19—H19B | 114.8 |
C10—C8—H8 | 115.9 | C19—C20—C18 | 59.7 (3) |
C10—C9—C8 | 60.2 (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 |
Experimental details
Crystal data | |
Chemical formula | [Zn(C10H8Br2NO)2] |
Mr | 701.36 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 7.5490 (15), 9.883 (2), 15.814 (3) |
α, β, γ (°) | 78.34 (3), 82.49 (2), 72.24 (3) |
V (Å3) | 1097.4 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 8.42 |
Crystal size (mm) | 0.21 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Bruker SMART 1000 CCD area detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.182, 0.187 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12652, 4962, 3772 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.650 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.086, 1.04 |
No. of reflections | 4962 |
No. of parameters | 262 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.65, −0.73 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1997), SHELXTL.
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
Recently, we have reported the structure of a Schiff base copper(II) complex (Yuan & Zhang, 2005). As an extension of our investigations in this area, we report here the title compound, a new mononuclear Schiff base zinc(II) complex, (I).
In (I), the Zn atom is four-coordinated by two N and two O atoms from two Schiff base ligands, forming a tetrahedral coordination (Fig. 1). The bond lengths and angles are comparable to the values observed in the similar Schiff base zinc(II) complexes (You, 2005a,b).