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metal-organic compounds
In the centrosymmetric title compound, [Zn(C15H13N2O2)2(C5H5N)2], the Zn atom is chelated by the O and N atoms of two bidentate ligands. The coordination geometry of the central Zn atom is octahedral. The crystal packing is stabilized by intermolecular C—HO interactions.
Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804011936/cv6317sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804011936/cv6317Isup2.hkl |
CCDC reference: 242291
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.064
- wR factor = 0.145
- Data-to-parameter ratio = 16.6
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.25 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT220_ALERT_2_C Large Non-Solvent C Ueq(max)/Ueq(min) ... 3.31 Ratio PLAT241_ALERT_2_C Check High U(eq) as Compared to Neighbors .... C3 PLAT380_ALERT_4_C Incorrectly Oriented X(sp2)-Methyl Moiety ...... C8 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 1 O2 -ZN1 -O2 -C9 0.00 55.00 3.756 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 10 N1 -ZN1 -N1 -C7 101.00100.00 3.756 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 15 N1 -ZN1 -N1 -N2 -81.00100.00 3.756 1.555 1.555 3.756 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 18 N3 -ZN1 -N3 -C16 -113.00100.00 3.756 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 23 N3 -ZN1 -N3 -C20 72.00100.00 3.756 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 10 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 3 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 7 ALERT type 4 Improvement, methodology, query or suggestion
Computing details top
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
Crystal data top
[Zn(C15H13N2O2)2(C5H5N)2] | F(000) = 760 |
Mr = 730.12 | Dx = 1.340 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 10.3531 (11) Å | Cell parameters from 2851 reflections |
b = 15.0133 (16) Å | θ = 1.9–27.0° |
c = 11.6892 (12) Å | µ = 0.73 mm−1 |
β = 95.138 (2)° | T = 293 K |
V = 1809.6 (3) Å3 | Block, light yellow |
Z = 2 | 0.29 × 0.20 × 0.16 mm |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 3933 independent reflections |
Radiation source: fine-focus sealed tube | 3304 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.026 |
Detector resolution: 83.66 pixels mm-1 | θmax = 27.0°, θmin = 1.9° |
ω scans | h = −13→11 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −19→15 |
Tmin = 0.817, Tmax = 0.892 | l = −13→14 |
9919 measured reflections |
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)] = 0.064 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.145 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.22 | w = 1/[σ2(Fo2) + (0.0583P)2 + 0.6177P] where P = (Fo2 + 2Fc2)/3 |
3933 reflections | (Δ/σ)max < 0.001 |
237 parameters | Δρmax = 0.54 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
x | y | z | Uiso*/Ueq | ||
Zn1 | 1.0000 | 0.0000 | 0.5000 | 0.03982 (17) | |
O1 | 0.6597 (3) | 0.0240 (2) | 0.1600 (3) | 0.0745 (9) | |
O2 | 1.09075 (19) | 0.11709 (13) | 0.53913 (17) | 0.0431 (5) | |
N1 | 0.9181 (2) | 0.01801 (15) | 0.3191 (2) | 0.0394 (6) | |
N2 | 1.1629 (2) | 0.05382 (16) | 0.7123 (2) | 0.0378 (5) | |
N3 | 0.8164 (2) | 0.05780 (18) | 0.5519 (2) | 0.0464 (6) | |
C1 | 0.9485 (5) | 0.1064 (3) | 0.0358 (3) | 0.0711 (11) | |
H1B | 1.0345 | 0.1214 | 0.0567 | 0.085* | |
C2 | 0.9000 (7) | 0.1148 (3) | −0.0769 (4) | 0.1006 (18) | |
H2C | 0.9537 | 0.1330 | −0.1321 | 0.121* | |
C3 | 0.7728 (8) | 0.0963 (3) | −0.1072 (4) | 0.116 (2) | |
H3A | 0.7389 | 0.1044 | −0.1829 | 0.139* | |
C4 | 0.6946 (5) | 0.0659 (3) | −0.0280 (4) | 0.0914 (16) | |
H4A | 0.6082 | 0.0528 | −0.0503 | 0.110* | |
C5 | 0.7431 (4) | 0.0542 (2) | 0.0864 (3) | 0.0612 (10) | |
C6 | 0.8713 (3) | 0.0757 (2) | 0.1197 (3) | 0.0476 (7) | |
C7 | 0.9310 (3) | 0.0764 (2) | 0.2406 (3) | 0.0431 (7) | |
C8 | 1.0184 (4) | 0.1537 (3) | 0.2727 (3) | 0.0701 (11) | |
H8A | 1.0519 | 0.1483 | 0.3517 | 0.105* | |
H8B | 0.9703 | 0.2082 | 0.2622 | 0.105* | |
H8C | 1.0890 | 0.1541 | 0.2248 | 0.105* | |
C9 | 1.1602 (2) | 0.11658 (18) | 0.6340 (2) | 0.0351 (6) | |
C10 | 1.2486 (3) | 0.19371 (18) | 0.6594 (2) | 0.0355 (6) | |
C11 | 1.3164 (3) | 0.2050 (2) | 0.7658 (3) | 0.0520 (8) | |
H11A | 1.3058 | 0.1648 | 0.8246 | 0.062* | |
C12 | 1.3999 (4) | 0.2763 (3) | 0.7844 (3) | 0.0662 (10) | |
H12A | 1.4455 | 0.2835 | 0.8560 | 0.079* | |
C13 | 1.4163 (4) | 0.3361 (3) | 0.6993 (3) | 0.0686 (11) | |
H13A | 1.4736 | 0.3835 | 0.7125 | 0.082* | |
C14 | 1.3482 (4) | 0.3260 (2) | 0.5947 (3) | 0.0603 (9) | |
H14A | 1.3587 | 0.3670 | 0.5366 | 0.072* | |
C15 | 1.2646 (3) | 0.2560 (2) | 0.5744 (3) | 0.0446 (7) | |
H15A | 1.2182 | 0.2502 | 0.5029 | 0.054* | |
C16 | 0.7190 (3) | 0.0096 (2) | 0.5837 (3) | 0.0537 (8) | |
H16A | 0.7301 | −0.0517 | 0.5903 | 0.064* | |
C17 | 0.6031 (3) | 0.0451 (3) | 0.6074 (3) | 0.0637 (10) | |
H17A | 0.5377 | 0.0087 | 0.6307 | 0.076* | |
C18 | 0.5846 (4) | 0.1341 (3) | 0.5965 (4) | 0.0733 (11) | |
H18A | 0.5058 | 0.1596 | 0.6105 | 0.088* | |
C19 | 0.6836 (4) | 0.1854 (3) | 0.5647 (4) | 0.0799 (12) | |
H19A | 0.6740 | 0.2468 | 0.5577 | 0.096* | |
C20 | 0.7975 (4) | 0.1450 (3) | 0.5432 (3) | 0.0661 (10) | |
H20A | 0.8648 | 0.1804 | 0.5214 | 0.079* | |
H1O | 0.695 (4) | −0.003 (2) | 0.209 (3) | 0.050 (11)* |
Atomic displacement parameters (Å2) top
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.0386 (3) | 0.0384 (3) | 0.0419 (3) | −0.0086 (2) | 0.00053 (19) | 0.0007 (2) |
O1 | 0.0497 (16) | 0.0660 (18) | 0.103 (2) | 0.0087 (13) | −0.0186 (16) | 0.0156 (17) |
O2 | 0.0464 (11) | 0.0396 (11) | 0.0419 (11) | −0.0096 (9) | −0.0028 (9) | 0.0049 (9) |
N1 | 0.0411 (13) | 0.0351 (13) | 0.0419 (13) | −0.0070 (10) | 0.0031 (10) | 0.0018 (10) |
N2 | 0.0409 (13) | 0.0352 (13) | 0.0373 (13) | −0.0062 (10) | 0.0034 (10) | 0.0034 (10) |
N3 | 0.0426 (14) | 0.0476 (16) | 0.0492 (15) | −0.0007 (11) | 0.0050 (11) | 0.0021 (12) |
C1 | 0.109 (3) | 0.056 (2) | 0.049 (2) | −0.005 (2) | 0.013 (2) | 0.0079 (17) |
C2 | 0.187 (6) | 0.070 (3) | 0.047 (2) | −0.009 (3) | 0.020 (3) | 0.007 (2) |
C3 | 0.221 (7) | 0.062 (3) | 0.055 (3) | −0.007 (4) | −0.046 (4) | 0.007 (2) |
C4 | 0.131 (4) | 0.047 (2) | 0.084 (3) | 0.000 (2) | −0.053 (3) | 0.001 (2) |
C5 | 0.080 (3) | 0.0322 (18) | 0.067 (2) | 0.0053 (16) | −0.018 (2) | 0.0017 (16) |
C6 | 0.069 (2) | 0.0324 (16) | 0.0409 (16) | 0.0022 (14) | 0.0004 (15) | 0.0012 (13) |
C7 | 0.0459 (17) | 0.0418 (17) | 0.0415 (16) | −0.0038 (13) | 0.0032 (13) | 0.0037 (13) |
C8 | 0.090 (3) | 0.061 (2) | 0.057 (2) | −0.034 (2) | −0.009 (2) | 0.0169 (18) |
C9 | 0.0333 (14) | 0.0351 (15) | 0.0378 (14) | −0.0003 (11) | 0.0087 (11) | −0.0046 (12) |
C10 | 0.0342 (14) | 0.0344 (15) | 0.0392 (15) | −0.0016 (11) | 0.0098 (11) | −0.0074 (12) |
C11 | 0.063 (2) | 0.052 (2) | 0.0409 (17) | −0.0147 (16) | 0.0069 (15) | −0.0052 (15) |
C12 | 0.074 (2) | 0.069 (3) | 0.054 (2) | −0.025 (2) | 0.0009 (18) | −0.0192 (19) |
C13 | 0.078 (3) | 0.053 (2) | 0.077 (3) | −0.0292 (19) | 0.020 (2) | −0.021 (2) |
C14 | 0.077 (2) | 0.0441 (19) | 0.062 (2) | −0.0160 (17) | 0.0206 (19) | −0.0023 (17) |
C15 | 0.0489 (17) | 0.0389 (16) | 0.0470 (17) | −0.0015 (13) | 0.0090 (13) | −0.0023 (14) |
C16 | 0.0522 (19) | 0.052 (2) | 0.058 (2) | −0.0044 (15) | 0.0077 (16) | −0.0042 (16) |
C17 | 0.048 (2) | 0.078 (3) | 0.066 (2) | −0.0047 (18) | 0.0119 (17) | −0.003 (2) |
C18 | 0.048 (2) | 0.091 (3) | 0.082 (3) | 0.020 (2) | 0.0090 (19) | −0.001 (2) |
C19 | 0.070 (3) | 0.061 (3) | 0.110 (3) | 0.021 (2) | 0.012 (2) | 0.010 (2) |
C20 | 0.058 (2) | 0.049 (2) | 0.092 (3) | 0.0042 (17) | 0.013 (2) | 0.013 (2) |
Geometric parameters (Å, º) top
Zn1—O2i | 2.0261 (19) | C7—C8 | 1.498 (4) |
Zn1—O2 | 2.0261 (19) | C8—H8A | 0.9600 |
Zn1—N3i | 2.222 (3) | C8—H8B | 0.9600 |
Zn1—N3 | 2.222 (3) | C8—H8C | 0.9600 |
Zn1—N1 | 2.223 (2) | C9—C10 | 1.489 (4) |
Zn1—N1i | 2.223 (2) | C10—C11 | 1.383 (4) |
O1—C5 | 1.351 (5) | C10—C15 | 1.385 (4) |
O1—H1O | 0.77 (4) | C11—C12 | 1.380 (5) |
O2—C9 | 1.267 (3) | C11—H11A | 0.9300 |
N1—C7 | 1.284 (4) | C12—C13 | 1.362 (5) |
N1—N2i | 1.395 (3) | C12—H12A | 0.9300 |
N2—C9 | 1.312 (4) | C13—C14 | 1.364 (5) |
N2—N1i | 1.395 (3) | C13—H13A | 0.9300 |
N3—C16 | 1.322 (4) | C14—C15 | 1.369 (4) |
N3—C20 | 1.327 (4) | C14—H14A | 0.9300 |
C1—C2 | 1.372 (6) | C15—H15A | 0.9300 |
C1—C6 | 1.398 (5) | C16—C17 | 1.363 (5) |
C1—H1B | 0.9300 | C16—H16A | 0.9300 |
C2—C3 | 1.362 (8) | C17—C18 | 1.354 (6) |
C2—H2C | 0.9300 | C17—H17A | 0.9300 |
C3—C4 | 1.362 (8) | C18—C19 | 1.360 (6) |
C3—H3A | 0.9300 | C18—H18A | 0.9300 |
C4—C5 | 1.397 (5) | C19—C20 | 1.369 (5) |
C4—H4A | 0.9300 | C19—H19A | 0.9300 |
C5—C6 | 1.387 (5) | C20—H20A | 0.9300 |
C6—C7 | 1.491 (4) | ||
O2i—Zn1—O2 | 180.00 (6) | C6—C7—C8 | 115.6 (3) |
O2i—Zn1—N3i | 89.44 (9) | C7—C8—H8A | 109.5 |
O2—Zn1—N3i | 90.56 (9) | C7—C8—H8B | 109.5 |
O2i—Zn1—N3 | 90.56 (9) | H8A—C8—H8B | 109.5 |
O2—Zn1—N3 | 89.44 (9) | C7—C8—H8C | 109.5 |
N3i—Zn1—N3 | 180.0 | H8A—C8—H8C | 109.5 |
O2i—Zn1—N1 | 76.19 (8) | H8B—C8—H8C | 109.5 |
O2—Zn1—N1 | 103.81 (8) | O2—C9—N2 | 126.2 (3) |
N3i—Zn1—N1 | 92.88 (9) | O2—C9—C10 | 117.4 (2) |
N3—Zn1—N1 | 87.12 (9) | N2—C9—C10 | 116.4 (2) |
O2i—Zn1—N1i | 103.81 (8) | C11—C10—C15 | 118.6 (3) |
O2—Zn1—N1i | 76.19 (8) | C11—C10—C9 | 121.9 (3) |
N3i—Zn1—N1i | 87.12 (9) | C15—C10—C9 | 119.6 (3) |
N3—Zn1—N1i | 92.88 (9) | C12—C11—C10 | 119.9 (3) |
N1—Zn1—N1i | 180.0 | C12—C11—H11A | 120.1 |
C5—O1—H1O | 111 (3) | C10—C11—H11A | 120.1 |
C9—O2—Zn1 | 114.07 (17) | C13—C12—C11 | 120.8 (3) |
C7—N1—N2i | 116.0 (2) | C13—C12—H12A | 119.6 |
C7—N1—Zn1 | 135.0 (2) | C11—C12—H12A | 119.6 |
N2i—N1—Zn1 | 108.97 (16) | C12—C13—C14 | 119.6 (3) |
C9—N2—N1i | 113.4 (2) | C12—C13—H13A | 120.2 |
C16—N3—C20 | 116.8 (3) | C14—C13—H13A | 120.2 |
C16—N3—Zn1 | 123.8 (2) | C13—C14—C15 | 120.5 (3) |
C20—N3—Zn1 | 119.3 (2) | C13—C14—H14A | 119.7 |
C2—C1—C6 | 121.4 (4) | C15—C14—H14A | 119.7 |
C2—C1—H1B | 119.3 | C14—C15—C10 | 120.6 (3) |
C6—C1—H1B | 119.3 | C14—C15—H15A | 119.7 |
C3—C2—C1 | 119.6 (5) | C10—C15—H15A | 119.7 |
C3—C2—H2C | 120.2 | N3—C16—C17 | 123.4 (3) |
C1—C2—H2C | 120.2 | N3—C16—H16A | 118.3 |
C2—C3—C4 | 120.7 (4) | C17—C16—H16A | 118.3 |
C2—C3—H3A | 119.6 | C18—C17—C16 | 119.1 (4) |
C4—C3—H3A | 119.6 | C18—C17—H17A | 120.5 |
C3—C4—C5 | 120.6 (5) | C16—C17—H17A | 120.5 |
C3—C4—H4A | 119.7 | C17—C18—C19 | 118.7 (4) |
C5—C4—H4A | 119.7 | C17—C18—H18A | 120.6 |
O1—C5—C6 | 123.3 (3) | C19—C18—H18A | 120.6 |
O1—C5—C4 | 117.1 (4) | C18—C19—C20 | 118.8 (4) |
C6—C5—C4 | 119.5 (4) | C18—C19—H19A | 120.6 |
C5—C6—C1 | 118.2 (3) | C20—C19—H19A | 120.6 |
C5—C6—C7 | 124.9 (3) | N3—C20—C19 | 123.2 (4) |
C1—C6—C7 | 116.6 (3) | N3—C20—H20A | 118.4 |
N1—C7—C6 | 127.7 (3) | C19—C20—H20A | 118.4 |
N1—C7—C8 | 116.7 (3) | ||
O2i—Zn1—O2—C9 | 0 (55) | C2—C1—C6—C5 | −0.4 (6) |
N3i—Zn1—O2—C9 | −77.37 (19) | C2—C1—C6—C7 | −175.1 (4) |
N3—Zn1—O2—C9 | 102.63 (19) | N2i—N1—C7—C6 | −1.0 (5) |
N1—Zn1—O2—C9 | −170.48 (18) | Zn1—N1—C7—C6 | 177.2 (2) |
N1i—Zn1—O2—C9 | 9.52 (18) | N2i—N1—C7—C8 | −179.6 (3) |
O2i—Zn1—N1—C7 | −169.7 (3) | Zn1—N1—C7—C8 | −1.5 (5) |
O2—Zn1—N1—C7 | 10.3 (3) | C5—C6—C7—N1 | 44.0 (5) |
N3i—Zn1—N1—C7 | −81.0 (3) | C1—C6—C7—N1 | −141.6 (4) |
N3—Zn1—N1—C7 | 99.0 (3) | C5—C6—C7—C8 | −137.4 (4) |
N1i—Zn1—N1—C7 | 101 (100) | C1—C6—C7—C8 | 37.0 (4) |
O2i—Zn1—N1—N2i | 8.53 (16) | Zn1—O2—C9—N2 | −10.1 (3) |
O2—Zn1—N1—N2i | −171.47 (16) | Zn1—O2—C9—C10 | 169.17 (17) |
N3i—Zn1—N1—N2i | 97.24 (18) | N1i—N2—C9—O2 | 1.8 (4) |
N3—Zn1—N1—N2i | −82.76 (18) | N1i—N2—C9—C10 | −177.5 (2) |
N1i—Zn1—N1—N2i | −81 (100) | O2—C9—C10—C11 | 171.9 (3) |
O2i—Zn1—N3—C16 | 22.6 (3) | N2—C9—C10—C11 | −8.7 (4) |
O2—Zn1—N3—C16 | −157.4 (3) | O2—C9—C10—C15 | −8.5 (4) |
N3i—Zn1—N3—C16 | −113 (100) | N2—C9—C10—C15 | 170.9 (3) |
N1—Zn1—N3—C16 | 98.8 (3) | C15—C10—C11—C12 | −1.3 (5) |
N1i—Zn1—N3—C16 | −81.2 (3) | C9—C10—C11—C12 | 178.3 (3) |
O2i—Zn1—N3—C20 | −152.2 (3) | C10—C11—C12—C13 | 0.2 (6) |
O2—Zn1—N3—C20 | 27.8 (3) | C11—C12—C13—C14 | 0.7 (6) |
N3i—Zn1—N3—C20 | 72 (100) | C12—C13—C14—C15 | −0.6 (6) |
N1—Zn1—N3—C20 | −76.1 (3) | C13—C14—C15—C10 | −0.6 (5) |
N1i—Zn1—N3—C20 | 103.9 (3) | C11—C10—C15—C14 | 1.5 (5) |
C6—C1—C2—C3 | 2.6 (7) | C9—C10—C15—C14 | −178.1 (3) |
C1—C2—C3—C4 | −2.8 (8) | C20—N3—C16—C17 | −0.1 (5) |
C2—C3—C4—C5 | 0.8 (8) | Zn1—N3—C16—C17 | −175.0 (3) |
C3—C4—C5—O1 | 179.9 (4) | N3—C16—C17—C18 | 1.0 (6) |
C3—C4—C5—C6 | 1.4 (6) | C16—C17—C18—C19 | −1.4 (6) |
O1—C5—C6—C1 | 180.0 (3) | C17—C18—C19—C20 | 1.0 (7) |
C4—C5—C6—C1 | −1.6 (5) | C16—N3—C20—C19 | −0.4 (6) |
O1—C5—C6—C7 | −5.7 (5) | Zn1—N3—C20—C19 | 174.8 (3) |
C4—C5—C6—C7 | 172.7 (3) | C18—C19—C20—N3 | 0.0 (7) |
Symmetry code: (i) −x+2, −y, −z+1. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1O···N1 | 0.77 (4) | 2.56 (4) | 3.120 (4) | 131 (3) |
O1—H1O···N2i | 0.77 (4) | 1.83 (4) | 2.545 (4) | 155 (3) |
C8—H8A···O2 | 0.96 | 2.24 | 3.185 (4) | 167 |
C20—H20A···O2 | 0.93 | 2.52 | 3.069 (5) | 118 |
C13—H13A···O1ii | 0.93 | 2.50 | 3.344 (5) | 152 |
Symmetry codes: (i) −x+2, −y, −z+1; (ii) x+1, −y+1/2, z+1/2. |
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