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In the mol­ecule of the title compound, [Zn(C2O4)(C10H8N2)]n, the coordination geometry around the zinc center can be described as slightly distorted octa­hedral. In the crystal structure, inter­molecular C—H...O hydrogen bonds link the mol­ecules, forming infinite chains. Hydrogen bonding and π–π stacking inter­actions stabilize the crystal structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806030893/hk2098sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806030893/hk2098Isup2.hkl
Contains datablock I

CCDC reference: 621360

Key indicators

  • Single-crystal X-ray study
  • T = 294 K
  • Mean [sigma](C-C) = 0.010 Å
  • R factor = 0.023
  • wR factor = 0.021
  • Data-to-parameter ratio = 8.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 10 PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C11 - C12 ... 1.56 Ang.
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 27.48 From the CIF: _reflns_number_total 1405 Count of symmetry unique reflns 1405 Completeness (_total/calc) 100.00% 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
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 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

Computing details top

Data collection: TEXSAN (Molecular Structure Corporation, 1998); cell refinement: TEXSAN; data reduction: TEXSAN; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1993); software used to prepare material for publication: SHELXL97.

catena-Poly[[(2,2'-bipyridine-κ2N,N')zinc(II)]-µ-oxalato] top
Crystal data top
[Zn(C2O4)(C10H8N2)]F(000) = 624
Mr = 309.57Dx = 1.738 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 1405 reflections
a = 9.1922 (5) Åθ = 2.7–27.5°
b = 9.1265 (5) ŵ = 2.09 mm1
c = 14.1060 (7) ÅT = 294 K
V = 1183.39 (11) Å3Needle, brown
Z = 40.41 × 0.06 × 0.03 mm
Data collection top
Rigaku Weissenberg IP
diffractometer
1405 independent reflections
Radiation source: fine-focus sealed tube766 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.059
ω scansθmax = 27.5°, θmin = 2.7°
Absorption correction: multi-scan
(TEXSAN; Molecular Structure Corporation, 1998)
h = 011
Tmin = 0.819, Tmax = 0.939k = 011
11070 measured reflectionsl = 180
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.023H-atom parameters constrained
wR(F2) = 0.021 w = 1/[σ2(Fo2) + (0.001P)2 + 0.0046P]
where P = (Fo2 + 2Fc2)/3
S = 0.97(Δ/σ)max < 0.001
1405 reflectionsΔρmax = 0.22 e Å3
172 parametersΔρmin = 0.22 e Å3
1 restraintAbsolute structure: Flack (1983), with 544 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.02 (4)
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
xyzUiso*/Ueq
Zn10.38151 (5)0.58966 (5)0.25330 (13)0.03991 (11)
N10.4492 (5)0.4009 (5)0.3303 (3)0.0440 (12)
N20.3019 (5)0.4123 (6)0.1696 (3)0.0399 (11)
O10.4960 (5)0.7390 (4)0.3397 (3)0.0467 (14)
O20.5714 (3)0.6164 (4)0.1730 (2)0.0437 (9)
O30.7757 (5)0.7475 (4)0.1729 (3)0.0440 (13)
O40.6970 (3)0.8734 (3)0.3353 (2)0.0413 (9)
C10.5187 (6)0.4014 (7)0.4134 (4)0.0514 (15)
H1C0.53860.49090.44220.062*
C20.5616 (9)0.2762 (8)0.4576 (6)0.067 (2)
H2C0.61140.28120.51490.080*
C30.5316 (8)0.1435 (7)0.4181 (5)0.068 (2)
H3A0.55950.05670.44750.081*
C40.4593 (8)0.1427 (8)0.3342 (5)0.0616 (19)
H4A0.43860.05330.30570.074*
C50.4153 (9)0.2713 (7)0.2895 (5)0.0391 (16)
C60.3354 (9)0.2790 (8)0.1981 (5)0.0437 (16)
C70.2962 (8)0.1529 (7)0.1498 (4)0.0592 (19)
H7A0.32040.06010.17200.071*
C80.2196 (8)0.1731 (8)0.0672 (5)0.073 (2)
H8A0.19220.09150.03200.087*
C90.1829 (8)0.3079 (8)0.0358 (5)0.0674 (19)
H9A0.13130.32050.02030.081*
C100.2257 (6)0.4277 (7)0.0910 (4)0.0569 (17)
H10A0.19960.52140.07150.068*
C110.6129 (7)0.7787 (6)0.3027 (4)0.0321 (13)
C120.6591 (7)0.7084 (6)0.2068 (4)0.0361 (14)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.0390 (2)0.0402 (2)0.0406 (2)0.0000 (4)0.0022 (4)0.0035 (6)
N10.043 (3)0.049 (3)0.040 (3)0.008 (3)0.003 (2)0.000 (3)
N20.047 (3)0.041 (3)0.032 (2)0.006 (3)0.007 (2)0.002 (3)
O10.037 (3)0.056 (3)0.048 (3)0.0095 (19)0.012 (3)0.008 (2)
O20.0410 (19)0.043 (2)0.0469 (19)0.0041 (19)0.0065 (16)0.011 (2)
O30.043 (3)0.056 (3)0.033 (2)0.0096 (18)0.011 (2)0.0095 (19)
O40.0405 (18)0.041 (2)0.0422 (19)0.0047 (18)0.0043 (16)0.0084 (18)
C10.058 (3)0.056 (4)0.040 (3)0.009 (4)0.008 (3)0.011 (4)
C20.073 (5)0.079 (5)0.047 (4)0.024 (4)0.016 (4)0.001 (4)
C30.090 (5)0.063 (5)0.050 (4)0.031 (4)0.007 (4)0.008 (3)
C40.072 (4)0.052 (4)0.061 (4)0.015 (4)0.002 (4)0.004 (4)
C50.050 (4)0.032 (3)0.035 (3)0.005 (3)0.013 (3)0.000 (2)
C60.040 (3)0.057 (4)0.035 (3)0.005 (4)0.001 (3)0.002 (3)
C70.077 (5)0.040 (4)0.061 (4)0.015 (3)0.003 (4)0.015 (3)
C80.083 (6)0.068 (5)0.067 (5)0.027 (4)0.006 (4)0.030 (5)
C90.070 (4)0.088 (5)0.045 (4)0.009 (5)0.016 (4)0.012 (4)
C100.059 (4)0.059 (4)0.052 (4)0.014 (4)0.008 (3)0.002 (4)
C110.028 (3)0.031 (3)0.037 (3)0.006 (3)0.002 (3)0.005 (3)
C120.043 (3)0.028 (3)0.037 (3)0.009 (3)0.001 (3)0.006 (3)
Geometric parameters (Å, º) top
Zn1—O4i2.080 (3)C1—H1C0.9300
Zn1—O22.094 (3)C2—C31.361 (9)
Zn1—O3i2.107 (4)C2—H2C0.9300
Zn1—O12.110 (5)C3—C41.357 (9)
Zn1—N12.129 (5)C3—H3A0.9300
Zn1—N22.133 (5)C4—C51.393 (9)
N1—C11.336 (7)C4—H4A0.9300
N1—C51.352 (8)C5—C61.485 (5)
N2—C61.317 (8)C7—C81.373 (9)
N2—C101.320 (7)C7—H7A0.9300
O1—C111.248 (7)C8—C91.351 (9)
O2—C121.258 (6)C8—H8A0.9300
O3—C121.227 (7)C9—C101.398 (8)
O3—Zn1ii2.107 (4)C9—H9A0.9300
O4—C111.247 (5)C10—H10A0.9300
O4—Zn1ii2.080 (3)C11—C121.556 (4)
C1—C21.360 (8)
O4i—Zn1—O2163.93 (9)C4—C3—C2117.4 (7)
O4i—Zn1—O3i78.96 (15)C4—C3—H3A121.3
O2—Zn1—O3i90.66 (16)C2—C3—H3A121.3
O4i—Zn1—O188.90 (16)C3—C4—C5122.2 (7)
O2—Zn1—O179.72 (16)C3—C4—H4A118.9
O3i—Zn1—O194.92 (13)C5—C4—H4A118.9
O4i—Zn1—N194.92 (15)N1—C5—C4118.5 (7)
O2—Zn1—N197.26 (16)N1—C5—C6116.2 (7)
O3i—Zn1—N1168.48 (17)C4—C5—C6125.3 (7)
O1—Zn1—N194.71 (19)N2—C6—C7123.8 (7)
O4i—Zn1—N298.68 (15)N2—C6—C5115.1 (7)
O2—Zn1—N294.31 (15)C7—C6—C5121.1 (7)
O3i—Zn1—N294.55 (18)C8—C7—C6116.1 (6)
O1—Zn1—N2168.85 (18)C8—C7—H7A122.0
N1—Zn1—N276.59 (13)C6—C7—H7A122.0
C1—N1—C5119.1 (6)C9—C8—C7121.9 (7)
C1—N1—Zn1125.8 (5)C9—C8—H8A119.1
C5—N1—Zn1115.1 (4)C7—C8—H8A119.1
C6—N2—C10118.6 (6)C8—C9—C10117.3 (6)
C6—N2—Zn1116.9 (4)C8—C9—H9A121.3
C10—N2—Zn1124.5 (5)C10—C9—H9A121.3
C11—O1—Zn1112.0 (4)N2—C10—C9122.3 (6)
C12—O2—Zn1114.0 (4)N2—C10—H10A118.9
C12—O3—Zn1ii113.5 (4)C9—C10—H10A118.9
C11—O4—Zn1ii114.4 (4)O4—C11—O1125.5 (6)
N1—C1—C2122.5 (7)O4—C11—C12115.9 (4)
N1—C1—H1C118.7O1—C11—C12118.6 (4)
C2—C1—H1C118.7O3—C12—O2127.4 (6)
C1—C2—C3120.1 (8)O3—C12—C11117.2 (5)
C1—C2—H2C120.0O2—C12—C11115.4 (4)
C3—C2—H2C120.0
O4i—Zn1—N1—C179.4 (5)C2—C3—C4—C50.6 (11)
O2—Zn1—N1—C190.1 (4)C1—N1—C5—C42.4 (11)
O3i—Zn1—N1—C1136.8 (9)Zn1—N1—C5—C4178.3 (5)
O1—Zn1—N1—C19.9 (5)C1—N1—C5—C6178.8 (4)
N2—Zn1—N1—C1177.2 (4)Zn1—N1—C5—C60.5 (6)
O4i—Zn1—N1—C599.8 (5)C3—C4—C5—N11.7 (12)
O2—Zn1—N1—C590.7 (5)C3—C4—C5—C6179.7 (5)
O3i—Zn1—N1—C542.5 (12)C10—N2—C6—C70.5 (11)
O1—Zn1—N1—C5170.9 (5)Zn1—N2—C6—C7177.7 (5)
N2—Zn1—N1—C52.1 (5)C10—N2—C6—C5177.3 (4)
O4i—Zn1—N2—C696.7 (5)Zn1—N2—C6—C54.5 (6)
O2—Zn1—N2—C692.8 (5)N1—C5—C6—N22.6 (5)
O3i—Zn1—N2—C6176.2 (5)C4—C5—C6—N2178.7 (9)
O1—Zn1—N2—C635.7 (13)N1—C5—C6—C7179.5 (9)
N1—Zn1—N2—C63.6 (6)C4—C5—C6—C70.8 (7)
O4i—Zn1—N2—C1085.2 (4)N2—C6—C7—C80.8 (12)
O2—Zn1—N2—C1085.3 (4)C5—C6—C7—C8178.5 (5)
O3i—Zn1—N2—C105.7 (5)C6—C7—C8—C90.9 (10)
O1—Zn1—N2—C10142.4 (9)C7—C8—C9—C100.2 (11)
N1—Zn1—N2—C10178.2 (4)C6—N2—C10—C91.7 (9)
O4i—Zn1—O1—C11164.8 (4)Zn1—N2—C10—C9176.4 (5)
O2—Zn1—O1—C113.8 (4)C8—C9—C10—N21.6 (10)
O3i—Zn1—O1—C1186.0 (4)Zn1ii—O4—C11—O1179.9 (4)
N1—Zn1—O1—C11100.4 (4)Zn1ii—O4—C11—C121.2 (4)
N2—Zn1—O1—C1162.1 (12)Zn1—O1—C11—O4174.9 (4)
O4i—Zn1—O2—C1242.2 (8)Zn1—O1—C11—C123.7 (5)
O3i—Zn1—O2—C1291.5 (4)Zn1ii—O3—C12—O2178.1 (5)
O1—Zn1—O2—C123.4 (4)Zn1ii—O3—C12—C112.4 (5)
N1—Zn1—O2—C1296.9 (4)Zn1—O2—C12—O3177.9 (5)
N2—Zn1—O2—C12173.9 (4)Zn1—O2—C12—C112.5 (4)
C5—N1—C1—C22.3 (9)O4—C11—C12—O32.5 (5)
Zn1—N1—C1—C2178.5 (6)O1—C11—C12—O3178.7 (7)
N1—C1—C2—C31.2 (12)O4—C11—C12—O2177.9 (6)
C1—C2—C3—C40.4 (12)O1—C11—C12—O20.9 (5)
Symmetry codes: (i) x1/2, y+3/2, z; (ii) x+1/2, y+3/2, z.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9A···O1iii0.932.413.279 (8)155
C2—H2C···O3iv0.932.483.395 (9)170
Symmetry codes: (iii) x+1/2, y1/2, z1/2; (iv) x+3/2, y1/2, z+1/2.
 

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