Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536803014570/dn6082sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536803014570/dn6082Isup2.hkl |
CCDC reference: 221620
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.010 Å
- R factor = 0.031
- wR factor = 0.076
- Data-to-parameter ratio = 15.1
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
PLAT_420 Alert C D-H Without Acceptor N10 - H10 ... ? PLAT_712 Alert C ANGLE Unknown or Inconsistent Label .......... ZN1 C11 O11 ZN1 General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 29.98 From the CIF: _reflns_number_total 2335 Count of symmetry unique reflns 2338 Completeness (_total/calc) 99.87% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present yes WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
2 Alert Level C = Please check
Data collection: CAD-4 EXPRESS (Enraf-Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: WinGX (Version 1.63.02; Farrugia, 1999).
[ZnBr2(C10H18N2O2)] | Dx = 1.791 Mg m−3 Dm = 1.78 (2) Mg m−3 Dm measured by flotation in CCl4 and C2H4Br2 |
Mr = 423.45 | Mo Kα radiation, λ = 0.71073 Å |
Tetragonal, P43 | Cell parameters from 25 reflections |
Hall symbol: P 4cw | θ = 6.5–9.9° |
a = 7.496 (2) Å | µ = 6.65 mm−1 |
c = 27.941 (5) Å | T = 293 K |
V = 1570.0 (7) Å3 | Parallelepiped, colourless |
Z = 4 | 0.40 × 0.38 × 0.28 mm |
F(000) = 832 |
Enraf–Nonius CAD-4 diffractometer | 1330 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.062 |
Graphite monochromator | θmax = 30.0°, θmin = 2.7° |
ω–2θ scans | h = −10→10 |
Absorption correction: multi-scan (Blessing, 1995) | k = 0→10 |
Tmin = 0.086, Tmax = 0.159 | l = 0→39 |
4956 measured reflections | 3 standard reflections every 1 min |
2335 independent reflections | intensity decay: 1% |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.031 | H-atom parameters constrained |
wR(F2) = 0.076 | w = 1/[σ2(Fo2) + (0.0339P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.95 | (Δ/σ)max < 0.001 |
2335 reflections | Δρmax = 0.32 e Å−3 |
155 parameters | Δρmin = −0.62 e Å−3 |
1 restraint | Absolute structure: Flack (1983) |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.015 (15) |
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 | ||
Zn | 0.46447 (8) | 0.59027 (7) | 0.10001 (2) | 0.04035 (15) | |
Br1 | 0.76449 (8) | 0.67589 (10) | 0.10419 (3) | 0.0628 (2) | |
Br2 | 0.28072 (10) | 0.64166 (12) | 0.16672 (3) | 0.0732 (2) | |
O2 | 0.4092 (6) | 1.3516 (5) | 0.07407 (16) | 0.0531 (11) | |
C2 | 0.3939 (8) | 1.2039 (7) | 0.09339 (19) | 0.0415 (14) | |
N3 | 0.2741 (7) | 1.0892 (6) | 0.07562 (17) | 0.0430 (11) | |
H3 | 0.2697 | 0.9837 | 0.0876 | 0.087 (6)* | |
C1 | 0.5041 (11) | 1.1457 (9) | 0.1345 (3) | 0.0646 (19) | |
H11 | 0.5029 | 1.0179 | 0.1365 | 0.087 (6)* | |
H12 | 0.4563 | 1.1951 | 0.1635 | 0.087 (6)* | |
H13 | 0.6244 | 1.1865 | 0.1302 | 0.087 (6)* | |
C4 | 0.1507 (7) | 1.1333 (7) | 0.0370 (2) | 0.0429 (12) | |
H4 | 0.2092 | 1.2174 | 0.0152 | 0.087 (6)* | |
C5 | −0.0163 (10) | 1.2213 (10) | 0.0575 (3) | 0.0691 (19) | |
H51 | −0.0715 | 1.1421 | 0.0806 | 0.087 (6)* | |
H52 | 0.0162 | 1.3307 | 0.0738 | 0.087 (6)* | |
C6 | −0.1470 (11) | 1.2622 (12) | 0.0179 (3) | 0.084 (3) | |
H61 | −0.2531 | 1.3164 | 0.0314 | 0.087 (6)* | |
H62 | −0.0938 | 1.3470 | −0.0041 | 0.087 (6)* | |
C7 | −0.1980 (11) | 1.0963 (12) | −0.0088 (3) | 0.081 (2) | |
H71 | −0.2791 | 1.1270 | −0.0346 | 0.087 (6)* | |
H72 | −0.2595 | 1.0153 | 0.0127 | 0.087 (6)* | |
C8 | −0.0331 (9) | 1.0034 (11) | −0.0295 (3) | 0.0604 (18) | |
H81 | −0.0687 | 0.8925 | −0.0447 | 0.087 (6)* | |
H82 | 0.0203 | 1.0790 | −0.0538 | 0.087 (6)* | |
C9 | 0.1040 (8) | 0.9645 (7) | 0.0093 (2) | 0.0416 (13) | |
H9 | 0.0533 | 0.8773 | 0.0316 | 0.087 (6)* | |
N10 | 0.2617 (6) | 0.8851 (6) | −0.01365 (18) | 0.0449 (11) | |
H10 | 0.2864 | 0.9164 | −0.0425 | 0.087 (6)* | |
C12 | 0.5190 (9) | 0.6932 (10) | −0.0194 (3) | 0.0638 (18) | |
H121 | 0.5204 | 0.7424 | −0.0511 | 0.087 (6)* | |
H122 | 0.5066 | 0.5659 | −0.0212 | 0.087 (6)* | |
H123 | 0.6286 | 0.7222 | −0.0034 | 0.087 (6)* | |
C11 | 0.3679 (7) | 0.7683 (7) | 0.0076 (2) | 0.0402 (13) | |
O11 | 0.3348 (6) | 0.7240 (5) | 0.05029 (16) | 0.0509 (10) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn | 0.0461 (3) | 0.0310 (3) | 0.0440 (3) | 0.0021 (3) | −0.0011 (3) | 0.0009 (3) |
Br1 | 0.0494 (3) | 0.0751 (4) | 0.0640 (4) | −0.0129 (3) | −0.0024 (3) | −0.0017 (4) |
Br2 | 0.0617 (4) | 0.1008 (6) | 0.0572 (4) | 0.0182 (4) | 0.0131 (4) | −0.0070 (4) |
O2 | 0.072 (3) | 0.034 (2) | 0.054 (3) | −0.0114 (19) | 0.001 (2) | −0.0018 (18) |
C2 | 0.053 (3) | 0.028 (2) | 0.043 (4) | 0.001 (2) | 0.006 (3) | −0.008 (2) |
N3 | 0.061 (3) | 0.024 (2) | 0.044 (3) | 0.001 (2) | −0.001 (2) | −0.0004 (19) |
C1 | 0.089 (5) | 0.048 (4) | 0.056 (4) | 0.004 (4) | −0.020 (4) | −0.008 (3) |
C4 | 0.047 (3) | 0.034 (3) | 0.048 (3) | 0.004 (2) | 0.000 (3) | 0.001 (2) |
C5 | 0.064 (4) | 0.071 (5) | 0.073 (5) | 0.026 (4) | 0.010 (4) | 0.000 (4) |
C6 | 0.062 (4) | 0.080 (6) | 0.109 (7) | 0.024 (4) | −0.003 (5) | 0.009 (5) |
C7 | 0.060 (5) | 0.093 (6) | 0.090 (7) | 0.002 (4) | −0.016 (4) | 0.014 (5) |
C8 | 0.050 (4) | 0.063 (4) | 0.069 (5) | 0.005 (3) | −0.018 (3) | 0.002 (3) |
C9 | 0.046 (3) | 0.037 (3) | 0.042 (3) | −0.002 (2) | 0.001 (2) | 0.005 (2) |
N10 | 0.053 (3) | 0.044 (2) | 0.038 (3) | 0.005 (2) | −0.003 (2) | 0.004 (2) |
C12 | 0.061 (4) | 0.068 (4) | 0.063 (4) | 0.018 (3) | −0.010 (3) | −0.020 (4) |
C11 | 0.042 (3) | 0.035 (3) | 0.044 (3) | 0.002 (2) | −0.007 (2) | −0.008 (2) |
O11 | 0.059 (3) | 0.042 (2) | 0.051 (3) | 0.0040 (19) | −0.007 (2) | 0.0152 (19) |
Zn—O11 | 1.970 (4) | C6—C7 | 1.500 (12) |
Zn—O2i | 1.974 (4) | C6—H61 | 0.9700 |
Zn—Br1 | 2.3416 (11) | C6—H62 | 0.9700 |
Zn—Br2 | 2.3495 (10) | C7—C8 | 1.532 (11) |
Zn—Znii | 7.496 (2) | C7—H71 | 0.9700 |
O2—C2 | 1.237 (7) | C7—H72 | 0.9700 |
C2—N3 | 1.339 (7) | C8—C9 | 1.522 (8) |
C2—C1 | 1.480 (9) | C8—H81 | 0.9700 |
N3—C4 | 1.460 (7) | C8—H82 | 0.9700 |
N3—H3 | 0.8600 | C9—N10 | 1.470 (8) |
C1—H11 | 0.9600 | C9—H9 | 0.9800 |
C1—H12 | 0.9600 | N10—C11 | 1.324 (7) |
C1—H13 | 0.9600 | N10—H10 | 0.8600 |
C4—C5 | 1.527 (8) | C12—C11 | 1.472 (8) |
C4—C9 | 1.524 (8) | C12—H121 | 0.9600 |
C4—H4 | 0.9800 | C12—H122 | 0.9600 |
C5—C6 | 1.509 (11) | C12—H123 | 0.9600 |
C5—H51 | 0.9700 | C11—O11 | 1.264 (7) |
C5—H52 | 0.9700 | ||
O11—Zn—O2i | 95.67 (18) | C7—C6—H61 | 109.4 |
O11—Zn—Br1 | 111.69 (13) | C5—C6—H61 | 109.4 |
O2i—Zn—Br1 | 117.92 (14) | C7—C6—H62 | 109.4 |
O11—Zn—Br2 | 100.76 (14) | C5—C6—H62 | 109.4 |
O2i—Zn—Br2 | 108.47 (14) | H61—C6—H62 | 108.0 |
Br1—Zn—Br2 | 118.59 (4) | C6—C7—C8 | 111.0 (7) |
O11—Zn—Znii | 59.41 (13) | C6—C7—H71 | 109.4 |
O2i—Zn—Znii | 154.99 (13) | C8—C7—H71 | 109.4 |
Br1—Zn—Znii | 74.09 (2) | C6—C7—H72 | 109.4 |
Br2—Zn—Znii | 80.56 (3) | C8—C7—H72 | 109.4 |
C2—O2—Znii | 132.1 (4) | H71—C7—H72 | 108.0 |
O2—C2—N3 | 118.4 (5) | C9—C8—C7 | 111.3 (6) |
O2—C2—C1 | 123.4 (5) | C9—C8—H81 | 109.4 |
N3—C2—C1 | 118.2 (5) | C7—C8—H81 | 109.4 |
C2—N3—C4 | 123.6 (4) | C9—C8—H82 | 109.4 |
C2—N3—H3 | 118.2 | C7—C8—H82 | 109.4 |
C4—N3—H3 | 118.2 | H81—C8—H82 | 108.0 |
C2—C1—H11 | 109.5 | N10—C9—C8 | 108.1 (5) |
C2—C1—H12 | 109.5 | N10—C9—C4 | 111.9 (5) |
H11—C1—H12 | 109.5 | C8—C9—C4 | 111.0 (5) |
C2—C1—H13 | 109.5 | N10—C9—H9 | 108.6 |
H11—C1—H13 | 109.5 | C8—C9—H9 | 108.6 |
H12—C1—H13 | 109.5 | C4—C9—H9 | 108.6 |
N3—C4—C5 | 109.8 (5) | C11—N10—C9 | 123.8 (5) |
N3—C4—C9 | 109.5 (4) | C11—N10—H10 | 118.1 |
C5—C4—C9 | 111.2 (5) | C9—N10—H10 | 118.1 |
N3—C4—H4 | 108.8 | C11—C12—H121 | 109.5 |
C5—C4—H4 | 108.8 | C11—C12—H122 | 109.5 |
C9—C4—H4 | 108.8 | H121—C12—H122 | 109.5 |
C6—C5—C4 | 110.1 (6) | C11—C12—H123 | 109.5 |
C6—C5—H51 | 109.6 | H121—C12—H123 | 109.5 |
C4—C5—H51 | 109.6 | H122—C12—H123 | 109.5 |
C6—C5—H52 | 109.6 | O11—C11—N10 | 118.6 (5) |
C4—C5—H52 | 109.6 | O11—C11—C12 | 122.3 (6) |
H51—C5—H52 | 108.1 | N10—C11—C12 | 119.1 (6) |
C7—C6—C5 | 111.2 (6) | C11—O11—Zn1 | 134.7 (4) |
Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z. |