Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807019836/ci2367sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807019836/ci2367Isup2.hkl |
CCDC reference: 646660
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.037
- wR factor = 0.096
- Data-to-parameter ratio = 17.5
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Zn - O1 .. 11.78 su PLAT232_ALERT_2_B Hirshfeld Test Diff (M-X) Zn - O2 .. 23.00 su
Alert level C PLAT060_ALERT_3_C Ratio Tmax/Tmin (Exp-to-Rep) (too) Large ....... 1.11 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.90 PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size ....... 0.70 mm PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) . 300 Ang. PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O2
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 1.901 Tmax scaled 0.644 Tmin scaled 0.578 PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 3 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
A mixture of ZnCO3 (0.4180 g, 3.33 mmol) and 2-chlorobenzoic acid (1.0438 g, 3.33 mmol) in ethanol (50 ml) was stirred at room temperature for 1 h and then filtered. An ethanol solution (50 ml) of methyl-3-pyridylcarbamate (1.0143 g, 3.33 mmol) was added to the filtrate and the mixture was stirred for 3 h. The resulting clear solution was allowed to stand in air at room temperature for two weeks, yielding colourless crystals of (I). The crystals were separated and dried at ambient temperature.
H atoms were placed in calculated positions [N–H = 0.86 Å and C–H = 0.93 (aromatic) or 0.96 Å (methyl)] and refined using a riding model, with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).
Compound (I) is a mononuclear zinc(II) compound (Fig. 1). The ZnII atom exists in a pseudo-octahedral coordination environment, created by two pyridine N atoms from two methyl-3-pyridylcarbamate (mpc) ligands and four O atoms from two bidentate 2-chlorobenzoate anions. But a tetrahedral arrangement is found for the ZnII atoms in related structures, viz. [Zn(benzoato)2(mpc)2] (Zeleňák et al., 2004) and [Zn(cinnamato)2(mpc)] (Zeleňák et al., 2007). The mean Zn–N distances of 2.032 Å (in the former) and 2.021 Å (in the latter) are shorter than that in compound (I) (2.181 Å), as expected for a tetrahedral arrangement. The Zn—O distances are in the range 2.0484 (16)–2.380 (2) Å, and the Zn—N and Zn—Cl distances are 2.1012 (18) and 2.546 (2) Å, respectively.
In the crystal structure of (I), the molecules are linked by N2–H2···O2ii and C8–H8···Clii [symmetry code: (ii) x, 1/2 - y, 1/2 + z] hydrogen bonds (Table 1), forming a chain along the c axis (Fig. 2).
The ZnII atom adopts a tetrahedral geometry in related complexes with methyl N-(3-pyridyl)carbamate ligands (Zeleňák et al., 2004, 2007).
Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: enCIFer (Allen et al., 2004).
[Zn(C7H4ClO2)2(C7H8N2O2)2] | F(000) = 1392 |
Mr = 680.78 | Dx = 1.574 Mg m−3 |
Orthorhombic, Pccn | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2ab 2ac | Cell parameters from 25 reflections |
a = 15.444 (3) Å | θ = 4.5–8.6° |
b = 13.650 (3) Å | µ = 1.10 mm−1 |
c = 13.627 (3) Å | T = 293 K |
V = 2872.7 (10) Å3 | Prism, colourless |
Z = 4 | 0.70 × 0.50 × 0.40 mm |
Siemens P4 diffractometer | 2566 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.021 |
Graphite monochromator | θmax = 28.0°, θmin = 2.5° |
2θ/ω scans | h = −1→20 |
Absorption correction: ψ scan (XEMP; Siemens, 1994) | k = −1→18 |
Tmin = 0.304, Tmax = 0.339 | l = −1→18 |
4275 measured reflections | 3 standard reflections every 97 reflections |
3429 independent reflections | intensity decay: 4.3% |
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) = 0.096 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0406P)2 + 0.9964P] where P = (Fo2 + 2Fc2)/3 |
3429 reflections | (Δ/σ)max = 0.001 |
196 parameters | Δρmax = 0.27 e Å−3 |
0 restraints | Δρmin = −0.36 e Å−3 |
[Zn(C7H4ClO2)2(C7H8N2O2)2] | V = 2872.7 (10) Å3 |
Mr = 680.78 | Z = 4 |
Orthorhombic, Pccn | Mo Kα radiation |
a = 15.444 (3) Å | µ = 1.10 mm−1 |
b = 13.650 (3) Å | T = 293 K |
c = 13.627 (3) Å | 0.70 × 0.50 × 0.40 mm |
Siemens P4 diffractometer | 2566 reflections with I > 2σ(I) |
Absorption correction: ψ scan (XEMP; Siemens, 1994) | Rint = 0.021 |
Tmin = 0.304, Tmax = 0.339 | 3 standard reflections every 97 reflections |
4275 measured reflections | intensity decay: 4.3% |
3429 independent reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.096 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.27 e Å−3 |
3429 reflections | Δρmin = −0.36 e Å−3 |
196 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 | ||
Zn | 0.2500 | 0.2500 | 0.00830 (3) | 0.04173 (11) | |
Cl | 0.02319 (4) | 0.17755 (6) | −0.27367 (6) | 0.0697 (2) | |
N1 | 0.30551 (11) | 0.34776 (13) | 0.10944 (13) | 0.0420 (4) | |
N2 | 0.22484 (13) | 0.47062 (13) | 0.32673 (15) | 0.0503 (5) | |
H2 | 0.1861 | 0.4281 | 0.3423 | 0.060* | |
O1 | 0.14614 (11) | 0.33727 (13) | −0.02481 (14) | 0.0577 (4) | |
O2 | 0.14705 (12) | 0.20595 (14) | −0.11392 (15) | 0.0677 (5) | |
O3 | 0.27541 (12) | 0.62242 (13) | 0.36654 (14) | 0.0632 (5) | |
O4 | 0.15579 (14) | 0.55887 (13) | 0.43625 (14) | 0.0683 (5) | |
C1 | 0.11059 (14) | 0.28121 (17) | −0.08633 (17) | 0.0458 (5) | |
C2 | 0.02036 (13) | 0.30729 (14) | −0.11921 (16) | 0.0402 (4) | |
C3 | −0.02401 (14) | 0.26336 (16) | −0.19616 (17) | 0.0450 (5) | |
C4 | −0.10918 (16) | 0.2880 (2) | −0.21635 (19) | 0.0567 (6) | |
H4 | −0.1382 | 0.2570 | −0.2675 | 0.068* | |
C5 | −0.15084 (17) | 0.3575 (2) | −0.1616 (2) | 0.0647 (7) | |
H5 | −0.2082 | 0.3732 | −0.1752 | 0.078* | |
C6 | −0.10790 (17) | 0.4042 (2) | −0.0863 (2) | 0.0643 (7) | |
H6 | −0.1356 | 0.4525 | −0.0499 | 0.077* | |
C7 | −0.02320 (15) | 0.37853 (18) | −0.06538 (18) | 0.0519 (5) | |
H7 | 0.0053 | 0.4097 | −0.0140 | 0.062* | |
C8 | 0.25616 (14) | 0.37803 (15) | 0.18363 (16) | 0.0423 (4) | |
H8 | 0.2005 | 0.3525 | 0.1891 | 0.051* | |
C9 | 0.28322 (14) | 0.44532 (15) | 0.25299 (15) | 0.0411 (4) | |
C10 | 0.36653 (15) | 0.48203 (17) | 0.24529 (17) | 0.0494 (5) | |
H10 | 0.3877 | 0.5266 | 0.2910 | 0.059* | |
C11 | 0.41724 (15) | 0.45099 (18) | 0.16834 (19) | 0.0539 (6) | |
H11 | 0.4732 | 0.4751 | 0.1612 | 0.065* | |
C12 | 0.38551 (14) | 0.38477 (18) | 0.10245 (17) | 0.0502 (5) | |
H12 | 0.4207 | 0.3647 | 0.0509 | 0.060* | |
C13 | 0.22424 (16) | 0.55699 (17) | 0.37586 (17) | 0.0492 (5) | |
C14 | 0.1445 (2) | 0.6486 (2) | 0.4903 (2) | 0.0798 (9) | |
H14A | 0.1280 | 0.7000 | 0.4461 | 0.120* | |
H14B | 0.1979 | 0.6656 | 0.5220 | 0.120* | |
H14C | 0.1001 | 0.6398 | 0.5388 | 0.120* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn | 0.04048 (17) | 0.04280 (18) | 0.0419 (2) | 0.00580 (14) | 0.000 | 0.000 |
Cl | 0.0637 (4) | 0.0734 (4) | 0.0720 (4) | −0.0131 (3) | 0.0083 (3) | −0.0261 (4) |
N1 | 0.0427 (8) | 0.0407 (9) | 0.0427 (10) | 0.0003 (7) | −0.0003 (8) | −0.0004 (7) |
N2 | 0.0636 (11) | 0.0395 (9) | 0.0477 (11) | −0.0067 (8) | 0.0129 (9) | −0.0020 (8) |
O1 | 0.0516 (9) | 0.0575 (10) | 0.0642 (11) | 0.0012 (8) | −0.0142 (8) | 0.0015 (8) |
O2 | 0.0678 (11) | 0.0697 (12) | 0.0656 (12) | 0.0302 (10) | −0.0050 (9) | −0.0042 (10) |
O3 | 0.0788 (12) | 0.0477 (9) | 0.0632 (11) | −0.0113 (9) | 0.0033 (9) | −0.0093 (8) |
O4 | 0.0933 (13) | 0.0544 (10) | 0.0572 (11) | −0.0041 (10) | 0.0267 (10) | −0.0112 (9) |
C1 | 0.0470 (11) | 0.0482 (11) | 0.0422 (12) | 0.0033 (10) | 0.0020 (9) | 0.0115 (9) |
C2 | 0.0443 (10) | 0.0386 (10) | 0.0378 (11) | 0.0021 (8) | 0.0008 (8) | 0.0102 (8) |
C3 | 0.0458 (11) | 0.0465 (12) | 0.0428 (11) | −0.0061 (9) | 0.0028 (9) | 0.0082 (9) |
C4 | 0.0503 (12) | 0.0734 (16) | 0.0463 (13) | −0.0089 (12) | −0.0075 (11) | 0.0143 (12) |
C5 | 0.0470 (12) | 0.0817 (19) | 0.0653 (17) | 0.0114 (13) | −0.0039 (12) | 0.0221 (15) |
C6 | 0.0609 (15) | 0.0689 (16) | 0.0633 (16) | 0.0260 (13) | 0.0045 (13) | 0.0061 (13) |
C7 | 0.0551 (13) | 0.0530 (13) | 0.0477 (13) | 0.0085 (11) | −0.0024 (10) | 0.0003 (10) |
C8 | 0.0417 (10) | 0.0370 (9) | 0.0481 (11) | −0.0023 (8) | 0.0017 (10) | 0.0004 (9) |
C9 | 0.0497 (10) | 0.0329 (9) | 0.0406 (11) | 0.0005 (8) | 0.0009 (9) | 0.0072 (9) |
C10 | 0.0540 (12) | 0.0459 (12) | 0.0484 (13) | −0.0060 (10) | −0.0070 (10) | −0.0027 (10) |
C11 | 0.0428 (11) | 0.0586 (14) | 0.0601 (15) | −0.0090 (10) | −0.0009 (10) | −0.0018 (12) |
C12 | 0.0437 (11) | 0.0585 (13) | 0.0484 (13) | −0.0012 (10) | 0.0032 (10) | 0.0003 (11) |
C13 | 0.0665 (13) | 0.0432 (11) | 0.0379 (11) | 0.0005 (10) | 0.0013 (10) | 0.0025 (9) |
C14 | 0.104 (2) | 0.0697 (18) | 0.0658 (19) | 0.0088 (17) | 0.0153 (17) | −0.0246 (15) |
Zn—O1 | 2.0484 (16) | C2—C7 | 1.391 (3) |
Zn—O1i | 2.0484 (16) | C3—C4 | 1.385 (3) |
Zn—N1 | 2.1012 (18) | C4—C5 | 1.368 (4) |
Zn—N1i | 2.1012 (18) | C4—H4 | 0.93 |
Zn—O2 | 2.380 (2) | C5—C6 | 1.378 (4) |
Zn—O2i | 2.380 (2) | C5—H5 | 0.93 |
Zn—C1i | 2.546 (2) | C6—C7 | 1.384 (3) |
Cl—C3 | 1.737 (2) | C6—H6 | 0.93 |
N1—C8 | 1.332 (3) | C7—H7 | 0.93 |
N1—C12 | 1.338 (3) | C8—C9 | 1.383 (3) |
N2—C13 | 1.356 (3) | C8—H8 | 0.93 |
N2—C9 | 1.394 (3) | C9—C10 | 1.385 (3) |
N2—H2 | 0.86 | C10—C11 | 1.376 (3) |
O1—C1 | 1.261 (3) | C10—H10 | 0.93 |
O2—C1 | 1.230 (3) | C11—C12 | 1.365 (3) |
O3—C13 | 1.199 (3) | C11—H11 | 0.93 |
O4—C13 | 1.340 (3) | C12—H12 | 0.93 |
O4—C14 | 1.439 (3) | C14—H14A | 0.96 |
C1—C2 | 1.506 (3) | C14—H14B | 0.96 |
C2—C3 | 1.389 (3) | C14—H14C | 0.96 |
O1—Zn—O1i | 154.55 (11) | C2—C3—Cl | 122.89 (17) |
O1—Zn—N1 | 95.43 (7) | C5—C4—C3 | 120.4 (2) |
O1i—Zn—N1 | 101.20 (7) | C5—C4—H4 | 119.8 |
O1—Zn—N1i | 101.20 (7) | C3—C4—H4 | 119.8 |
O1i—Zn—N1i | 95.43 (7) | C4—C5—C6 | 120.0 (2) |
N1—Zn—N1i | 98.02 (10) | C4—C5—H5 | 120.0 |
O1—Zn—O2 | 57.97 (6) | C6—C5—H5 | 120.0 |
O1i—Zn—O2 | 102.83 (7) | C5—C6—C7 | 119.4 (3) |
N1—Zn—O2 | 153.14 (6) | C5—C6—H6 | 120.3 |
N1i—Zn—O2 | 91.49 (7) | C7—C6—H6 | 120.3 |
O1—Zn—O2i | 102.83 (7) | C6—C7—C2 | 121.7 (2) |
O1i—Zn—O2i | 57.97 (6) | C6—C7—H7 | 119.2 |
N1—Zn—O2i | 91.49 (7) | C2—C7—H7 | 119.2 |
N1i—Zn—O2i | 153.14 (6) | N1—C8—C9 | 123.51 (19) |
O2—Zn—O2i | 91.17 (10) | N1—C8—H8 | 118.2 |
O1—Zn—C1i | 130.40 (8) | C9—C8—H8 | 118.2 |
O1i—Zn—C1i | 29.39 (7) | C8—C9—C10 | 118.0 (2) |
N1—Zn—C1i | 95.36 (7) | C8—C9—N2 | 117.5 (2) |
N1i—Zn—C1i | 124.83 (7) | C10—C9—N2 | 124.5 (2) |
O2—Zn—C1i | 99.69 (7) | C11—C10—C9 | 118.4 (2) |
O2i—Zn—C1i | 28.68 (7) | C11—C10—H10 | 120.8 |
C8—N1—C12 | 117.73 (19) | C9—C10—H10 | 120.8 |
C8—N1—Zn | 117.48 (14) | C12—C11—C10 | 120.1 (2) |
C12—N1—Zn | 124.73 (15) | C12—C11—H11 | 120.0 |
C13—N2—C9 | 125.2 (2) | C10—C11—H11 | 120.0 |
C13—N2—H2 | 117.4 | N1—C12—C11 | 122.3 (2) |
C9—N2—H2 | 117.4 | N1—C12—H12 | 118.8 |
C1—O1—Zn | 97.73 (14) | C11—C12—H12 | 118.8 |
C1—O2—Zn | 83.16 (15) | O3—C13—O4 | 124.8 (2) |
C13—O4—C14 | 115.2 (2) | O3—C13—N2 | 126.2 (2) |
O2—C1—O1 | 120.7 (2) | O4—C13—N2 | 109.0 (2) |
O2—C1—C2 | 122.0 (2) | O4—C14—H14A | 109.5 |
O1—C1—C2 | 117.2 (2) | O4—C14—H14B | 109.5 |
C3—C2—C7 | 117.46 (19) | H14A—C14—H14B | 109.5 |
C3—C2—C1 | 125.4 (2) | O4—C14—H14C | 109.5 |
C7—C2—C1 | 117.1 (2) | H14A—C14—H14C | 109.5 |
C4—C3—C2 | 120.9 (2) | H14B—C14—H14C | 109.5 |
C4—C3—Cl | 116.18 (19) | ||
O1—Zn—N1—C8 | 55.12 (16) | O2—C1—C2—C7 | 163.7 (2) |
O1i—Zn—N1—C8 | −144.24 (15) | O1—C1—C2—C7 | −12.7 (3) |
N1i—Zn—N1—C8 | −47.03 (13) | C7—C2—C3—C4 | −1.8 (3) |
O2—Zn—N1—C8 | 62.6 (2) | C1—C2—C3—C4 | 175.5 (2) |
O2i—Zn—N1—C8 | 158.16 (15) | C7—C2—C3—Cl | 176.85 (17) |
C1i—Zn—N1—C8 | −173.37 (15) | C1—C2—C3—Cl | −5.9 (3) |
O1—Zn—N1—C12 | −122.03 (18) | C2—C3—C4—C5 | 1.1 (3) |
O1i—Zn—N1—C12 | 38.62 (19) | Cl—C3—C4—C5 | −177.63 (19) |
N1i—Zn—N1—C12 | 135.8 (2) | C3—C4—C5—C6 | 0.6 (4) |
O2—Zn—N1—C12 | −114.5 (2) | C4—C5—C6—C7 | −1.5 (4) |
O2i—Zn—N1—C12 | −18.99 (18) | C5—C6—C7—C2 | 0.7 (4) |
C1i—Zn—N1—C12 | 9.49 (19) | C3—C2—C7—C6 | 0.9 (3) |
O1i—Zn—O1—C1 | 48.91 (13) | C1—C2—C7—C6 | −176.6 (2) |
N1—Zn—O1—C1 | 179.75 (14) | C12—N1—C8—C9 | 0.1 (3) |
N1i—Zn—O1—C1 | −80.94 (15) | Zn—N1—C8—C9 | −177.22 (16) |
O2—Zn—O1—C1 | 3.74 (13) | N1—C8—C9—C10 | −0.9 (3) |
O2i—Zn—O1—C1 | 86.97 (15) | N1—C8—C9—N2 | 179.92 (19) |
C1i—Zn—O1—C1 | 77.97 (19) | C13—N2—C9—C8 | −153.2 (2) |
O1—Zn—O2—C1 | −3.83 (13) | C13—N2—C9—C10 | 27.6 (4) |
O1i—Zn—O2—C1 | −165.62 (14) | C8—C9—C10—C11 | 1.1 (3) |
N1—Zn—O2—C1 | −12.6 (2) | N2—C9—C10—C11 | −179.7 (2) |
N1i—Zn—O2—C1 | 98.47 (15) | C9—C10—C11—C12 | −0.7 (4) |
O2i—Zn—O2—C1 | −108.26 (15) | C8—N1—C12—C11 | 0.3 (3) |
C1i—Zn—O2—C1 | −135.80 (13) | Zn—N1—C12—C11 | 177.46 (18) |
Zn—O2—C1—O1 | 6.1 (2) | C10—C11—C12—N1 | 0.0 (4) |
Zn—O2—C1—C2 | −170.09 (19) | C14—O4—C13—O3 | 1.7 (4) |
Zn—O1—C1—O2 | −7.2 (2) | C14—O4—C13—N2 | −177.3 (2) |
Zn—O1—C1—C2 | 169.25 (16) | C9—N2—C13—O3 | −3.4 (4) |
O2—C1—C2—C3 | −13.6 (3) | C9—N2—C13—O4 | 175.6 (2) |
O1—C1—C2—C3 | 170.0 (2) |
Symmetry code: (i) −x+1/2, −y+1/2, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O2ii | 0.86 | 2.02 | 2.812 (3) | 153 |
C8—H8···Clii | 0.93 | 2.82 | 3.723 (2) | 165 |
Symmetry code: (ii) x, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | [Zn(C7H4ClO2)2(C7H8N2O2)2] |
Mr | 680.78 |
Crystal system, space group | Orthorhombic, Pccn |
Temperature (K) | 293 |
a, b, c (Å) | 15.444 (3), 13.650 (3), 13.627 (3) |
V (Å3) | 2872.7 (10) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.10 |
Crystal size (mm) | 0.70 × 0.50 × 0.40 |
Data collection | |
Diffractometer | Siemens P4 |
Absorption correction | ψ scan (XEMP; Siemens, 1994) |
Tmin, Tmax | 0.304, 0.339 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4275, 3429, 2566 |
Rint | 0.021 |
(sin θ/λ)max (Å−1) | 0.661 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.096, 1.02 |
No. of reflections | 3429 |
No. of parameters | 196 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.27, −0.36 |
Computer programs: XSCANS (Siemens, 1994), XSCANS, SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997), enCIFer (Allen et al., 2004).
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2···O2i | 0.86 | 2.02 | 2.812 (3) | 153 |
C8—H8···Cli | 0.93 | 2.82 | 3.723 (2) | 165 |
Symmetry code: (i) x, −y+1/2, z+1/2. |
Compound (I) is a mononuclear zinc(II) compound (Fig. 1). The ZnII atom exists in a pseudo-octahedral coordination environment, created by two pyridine N atoms from two methyl-3-pyridylcarbamate (mpc) ligands and four O atoms from two bidentate 2-chlorobenzoate anions. But a tetrahedral arrangement is found for the ZnII atoms in related structures, viz. [Zn(benzoato)2(mpc)2] (Zeleňák et al., 2004) and [Zn(cinnamato)2(mpc)] (Zeleňák et al., 2007). The mean Zn–N distances of 2.032 Å (in the former) and 2.021 Å (in the latter) are shorter than that in compound (I) (2.181 Å), as expected for a tetrahedral arrangement. The Zn—O distances are in the range 2.0484 (16)–2.380 (2) Å, and the Zn—N and Zn—Cl distances are 2.1012 (18) and 2.546 (2) Å, respectively.
In the crystal structure of (I), the molecules are linked by N2–H2···O2ii and C8–H8···Clii [symmetry code: (ii) x, 1/2 - y, 1/2 + z] hydrogen bonds (Table 1), forming a chain along the c axis (Fig. 2).