In the molecule of the title compound, [Zn(C
2O
4)(C
10H
8N
2)]
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
CCDC reference: 621360
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (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
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 = 309.57 | Dx = 1.738 Mg m−3 |
Orthorhombic, Pna21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2c -2n | Cell parameters from 1405 reflections |
a = 9.1922 (5) Å | θ = 2.7–27.5° |
b = 9.1265 (5) Å | µ = 2.09 mm−1 |
c = 14.1060 (7) Å | T = 294 K |
V = 1183.39 (11) Å3 | Needle, brown |
Z = 4 | 0.41 × 0.06 × 0.03 mm |
Data collection top
Rigaku Weissenberg IP diffractometer | 1405 independent reflections |
Radiation source: fine-focus sealed tube | 766 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.059 |
ω scans | θmax = 27.5°, θmin = 2.7° |
Absorption correction: multi-scan (TEXSAN; Molecular Structure Corporation, 1998) | h = 0→11 |
Tmin = 0.819, Tmax = 0.939 | k = 0→11 |
11070 measured reflections | l = −18→0 |
Refinement top
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)] = 0.023 | H-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 reflections | Δρmax = 0.22 e Å−3 |
172 parameters | Δρmin = −0.22 e Å−3 |
1 restraint | Absolute structure: Flack (1983), with 544 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute 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 | x | y | z | Uiso*/Ueq | |
Zn1 | 0.38151 (5) | 0.58966 (5) | 0.25330 (13) | 0.03991 (11) | |
N1 | 0.4492 (5) | 0.4009 (5) | 0.3303 (3) | 0.0440 (12) | |
N2 | 0.3019 (5) | 0.4123 (6) | 0.1696 (3) | 0.0399 (11) | |
O1 | 0.4960 (5) | 0.7390 (4) | 0.3397 (3) | 0.0467 (14) | |
O2 | 0.5714 (3) | 0.6164 (4) | 0.1730 (2) | 0.0437 (9) | |
O3 | 0.7757 (5) | 0.7475 (4) | 0.1729 (3) | 0.0440 (13) | |
O4 | 0.6970 (3) | 0.8734 (3) | 0.3353 (2) | 0.0413 (9) | |
C1 | 0.5187 (6) | 0.4014 (7) | 0.4134 (4) | 0.0514 (15) | |
H1C | 0.5386 | 0.4909 | 0.4422 | 0.062* | |
C2 | 0.5616 (9) | 0.2762 (8) | 0.4576 (6) | 0.067 (2) | |
H2C | 0.6114 | 0.2812 | 0.5149 | 0.080* | |
C3 | 0.5316 (8) | 0.1435 (7) | 0.4181 (5) | 0.068 (2) | |
H3A | 0.5595 | 0.0567 | 0.4475 | 0.081* | |
C4 | 0.4593 (8) | 0.1427 (8) | 0.3342 (5) | 0.0616 (19) | |
H4A | 0.4386 | 0.0533 | 0.3057 | 0.074* | |
C5 | 0.4153 (9) | 0.2713 (7) | 0.2895 (5) | 0.0391 (16) | |
C6 | 0.3354 (9) | 0.2790 (8) | 0.1981 (5) | 0.0437 (16) | |
C7 | 0.2962 (8) | 0.1529 (7) | 0.1498 (4) | 0.0592 (19) | |
H7A | 0.3204 | 0.0601 | 0.1720 | 0.071* | |
C8 | 0.2196 (8) | 0.1731 (8) | 0.0672 (5) | 0.073 (2) | |
H8A | 0.1922 | 0.0915 | 0.0320 | 0.087* | |
C9 | 0.1829 (8) | 0.3079 (8) | 0.0358 (5) | 0.0674 (19) | |
H9A | 0.1313 | 0.3205 | −0.0203 | 0.081* | |
C10 | 0.2257 (6) | 0.4277 (7) | 0.0910 (4) | 0.0569 (17) | |
H10A | 0.1996 | 0.5214 | 0.0715 | 0.068* | |
C11 | 0.6129 (7) | 0.7787 (6) | 0.3027 (4) | 0.0321 (13) | |
C12 | 0.6591 (7) | 0.7084 (6) | 0.2068 (4) | 0.0361 (14) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.0390 (2) | 0.0402 (2) | 0.0406 (2) | 0.0000 (4) | 0.0022 (4) | −0.0035 (6) |
N1 | 0.043 (3) | 0.049 (3) | 0.040 (3) | 0.008 (3) | −0.003 (2) | 0.000 (3) |
N2 | 0.047 (3) | 0.041 (3) | 0.032 (2) | −0.006 (3) | −0.007 (2) | −0.002 (3) |
O1 | 0.037 (3) | 0.056 (3) | 0.048 (3) | −0.0095 (19) | 0.012 (3) | −0.008 (2) |
O2 | 0.0410 (19) | 0.043 (2) | 0.0469 (19) | −0.0041 (19) | 0.0065 (16) | −0.011 (2) |
O3 | 0.043 (3) | 0.056 (3) | 0.033 (2) | −0.0096 (18) | 0.011 (2) | −0.0095 (19) |
O4 | 0.0405 (18) | 0.041 (2) | 0.0422 (19) | −0.0047 (18) | 0.0043 (16) | −0.0084 (18) |
C1 | 0.058 (3) | 0.056 (4) | 0.040 (3) | 0.009 (4) | −0.008 (3) | −0.011 (4) |
C2 | 0.073 (5) | 0.079 (5) | 0.047 (4) | 0.024 (4) | −0.016 (4) | 0.001 (4) |
C3 | 0.090 (5) | 0.063 (5) | 0.050 (4) | 0.031 (4) | −0.007 (4) | 0.008 (3) |
C4 | 0.072 (4) | 0.052 (4) | 0.061 (4) | 0.015 (4) | −0.002 (4) | −0.004 (4) |
C5 | 0.050 (4) | 0.032 (3) | 0.035 (3) | 0.005 (3) | 0.013 (3) | 0.000 (2) |
C6 | 0.040 (3) | 0.057 (4) | 0.035 (3) | −0.005 (4) | −0.001 (3) | −0.002 (3) |
C7 | 0.077 (5) | 0.040 (4) | 0.061 (4) | −0.015 (3) | 0.003 (4) | −0.015 (3) |
C8 | 0.083 (6) | 0.068 (5) | 0.067 (5) | −0.027 (4) | −0.006 (4) | −0.030 (5) |
C9 | 0.070 (4) | 0.088 (5) | 0.045 (4) | −0.009 (5) | −0.016 (4) | −0.012 (4) |
C10 | 0.059 (4) | 0.059 (4) | 0.052 (4) | −0.014 (4) | −0.008 (3) | −0.002 (4) |
C11 | 0.028 (3) | 0.031 (3) | 0.037 (3) | 0.006 (3) | −0.002 (3) | −0.005 (3) |
C12 | 0.043 (3) | 0.028 (3) | 0.037 (3) | 0.009 (3) | −0.001 (3) | 0.006 (3) |
Geometric parameters (Å, º) top
Zn1—O4i | 2.080 (3) | C1—H1C | 0.9300 |
Zn1—O2 | 2.094 (3) | C2—C3 | 1.361 (9) |
Zn1—O3i | 2.107 (4) | C2—H2C | 0.9300 |
Zn1—O1 | 2.110 (5) | C3—C4 | 1.357 (9) |
Zn1—N1 | 2.129 (5) | C3—H3A | 0.9300 |
Zn1—N2 | 2.133 (5) | C4—C5 | 1.393 (9) |
N1—C1 | 1.336 (7) | C4—H4A | 0.9300 |
N1—C5 | 1.352 (8) | C5—C6 | 1.485 (5) |
N2—C6 | 1.317 (8) | C7—C8 | 1.373 (9) |
N2—C10 | 1.320 (7) | C7—H7A | 0.9300 |
O1—C11 | 1.248 (7) | C8—C9 | 1.351 (9) |
O2—C12 | 1.258 (6) | C8—H8A | 0.9300 |
O3—C12 | 1.227 (7) | C9—C10 | 1.398 (8) |
O3—Zn1ii | 2.107 (4) | C9—H9A | 0.9300 |
O4—C11 | 1.247 (5) | C10—H10A | 0.9300 |
O4—Zn1ii | 2.080 (3) | C11—C12 | 1.556 (4) |
C1—C2 | 1.360 (8) | | |
| | | |
O4i—Zn1—O2 | 163.93 (9) | C4—C3—C2 | 117.4 (7) |
O4i—Zn1—O3i | 78.96 (15) | C4—C3—H3A | 121.3 |
O2—Zn1—O3i | 90.66 (16) | C2—C3—H3A | 121.3 |
O4i—Zn1—O1 | 88.90 (16) | C3—C4—C5 | 122.2 (7) |
O2—Zn1—O1 | 79.72 (16) | C3—C4—H4A | 118.9 |
O3i—Zn1—O1 | 94.92 (13) | C5—C4—H4A | 118.9 |
O4i—Zn1—N1 | 94.92 (15) | N1—C5—C4 | 118.5 (7) |
O2—Zn1—N1 | 97.26 (16) | N1—C5—C6 | 116.2 (7) |
O3i—Zn1—N1 | 168.48 (17) | C4—C5—C6 | 125.3 (7) |
O1—Zn1—N1 | 94.71 (19) | N2—C6—C7 | 123.8 (7) |
O4i—Zn1—N2 | 98.68 (15) | N2—C6—C5 | 115.1 (7) |
O2—Zn1—N2 | 94.31 (15) | C7—C6—C5 | 121.1 (7) |
O3i—Zn1—N2 | 94.55 (18) | C8—C7—C6 | 116.1 (6) |
O1—Zn1—N2 | 168.85 (18) | C8—C7—H7A | 122.0 |
N1—Zn1—N2 | 76.59 (13) | C6—C7—H7A | 122.0 |
C1—N1—C5 | 119.1 (6) | C9—C8—C7 | 121.9 (7) |
C1—N1—Zn1 | 125.8 (5) | C9—C8—H8A | 119.1 |
C5—N1—Zn1 | 115.1 (4) | C7—C8—H8A | 119.1 |
C6—N2—C10 | 118.6 (6) | C8—C9—C10 | 117.3 (6) |
C6—N2—Zn1 | 116.9 (4) | C8—C9—H9A | 121.3 |
C10—N2—Zn1 | 124.5 (5) | C10—C9—H9A | 121.3 |
C11—O1—Zn1 | 112.0 (4) | N2—C10—C9 | 122.3 (6) |
C12—O2—Zn1 | 114.0 (4) | N2—C10—H10A | 118.9 |
C12—O3—Zn1ii | 113.5 (4) | C9—C10—H10A | 118.9 |
C11—O4—Zn1ii | 114.4 (4) | O4—C11—O1 | 125.5 (6) |
N1—C1—C2 | 122.5 (7) | O4—C11—C12 | 115.9 (4) |
N1—C1—H1C | 118.7 | O1—C11—C12 | 118.6 (4) |
C2—C1—H1C | 118.7 | O3—C12—O2 | 127.4 (6) |
C1—C2—C3 | 120.1 (8) | O3—C12—C11 | 117.2 (5) |
C1—C2—H2C | 120.0 | O2—C12—C11 | 115.4 (4) |
C3—C2—H2C | 120.0 | | |
| | | |
O4i—Zn1—N1—C1 | −79.4 (5) | C2—C3—C4—C5 | −0.6 (11) |
O2—Zn1—N1—C1 | 90.1 (4) | C1—N1—C5—C4 | −2.4 (11) |
O3i—Zn1—N1—C1 | −136.8 (9) | Zn1—N1—C5—C4 | 178.3 (5) |
O1—Zn1—N1—C1 | 9.9 (5) | C1—N1—C5—C6 | 178.8 (4) |
N2—Zn1—N1—C1 | −177.2 (4) | Zn1—N1—C5—C6 | −0.5 (6) |
O4i—Zn1—N1—C5 | 99.8 (5) | C3—C4—C5—N1 | 1.7 (12) |
O2—Zn1—N1—C5 | −90.7 (5) | C3—C4—C5—C6 | −179.7 (5) |
O3i—Zn1—N1—C5 | 42.5 (12) | C10—N2—C6—C7 | 0.5 (11) |
O1—Zn1—N1—C5 | −170.9 (5) | Zn1—N2—C6—C7 | −177.7 (5) |
N2—Zn1—N1—C5 | 2.1 (5) | C10—N2—C6—C5 | −177.3 (4) |
O4i—Zn1—N2—C6 | −96.7 (5) | Zn1—N2—C6—C5 | 4.5 (6) |
O2—Zn1—N2—C6 | 92.8 (5) | N1—C5—C6—N2 | −2.6 (5) |
O3i—Zn1—N2—C6 | −176.2 (5) | C4—C5—C6—N2 | 178.7 (9) |
O1—Zn1—N2—C6 | 35.7 (13) | N1—C5—C6—C7 | 179.5 (9) |
N1—Zn1—N2—C6 | −3.6 (6) | C4—C5—C6—C7 | 0.8 (7) |
O4i—Zn1—N2—C10 | 85.2 (4) | N2—C6—C7—C8 | 0.8 (12) |
O2—Zn1—N2—C10 | −85.3 (4) | C5—C6—C7—C8 | 178.5 (5) |
O3i—Zn1—N2—C10 | 5.7 (5) | C6—C7—C8—C9 | −0.9 (10) |
O1—Zn1—N2—C10 | −142.4 (9) | C7—C8—C9—C10 | −0.2 (11) |
N1—Zn1—N2—C10 | 178.2 (4) | C6—N2—C10—C9 | −1.7 (9) |
O4i—Zn1—O1—C11 | −164.8 (4) | Zn1—N2—C10—C9 | 176.4 (5) |
O2—Zn1—O1—C11 | 3.8 (4) | C8—C9—C10—N2 | 1.6 (10) |
O3i—Zn1—O1—C11 | −86.0 (4) | Zn1ii—O4—C11—O1 | −179.9 (4) |
N1—Zn1—O1—C11 | 100.4 (4) | Zn1ii—O4—C11—C12 | −1.2 (4) |
N2—Zn1—O1—C11 | 62.1 (12) | Zn1—O1—C11—O4 | 174.9 (4) |
O4i—Zn1—O2—C12 | 42.2 (8) | Zn1—O1—C11—C12 | −3.7 (5) |
O3i—Zn1—O2—C12 | 91.5 (4) | Zn1ii—O3—C12—O2 | 178.1 (5) |
O1—Zn1—O2—C12 | −3.4 (4) | Zn1ii—O3—C12—C11 | −2.4 (5) |
N1—Zn1—O2—C12 | −96.9 (4) | Zn1—O2—C12—O3 | −177.9 (5) |
N2—Zn1—O2—C12 | −173.9 (4) | Zn1—O2—C12—C11 | 2.5 (4) |
C5—N1—C1—C2 | 2.3 (9) | O4—C11—C12—O3 | 2.5 (5) |
Zn1—N1—C1—C2 | −178.5 (6) | O1—C11—C12—O3 | −178.7 (7) |
N1—C1—C2—C3 | −1.2 (12) | O4—C11—C12—O2 | −177.9 (6) |
C1—C2—C3—C4 | 0.4 (12) | O1—C11—C12—O2 | 0.9 (5) |
Symmetry codes: (i) x−1/2, −y+3/2, z; (ii) x+1/2, −y+3/2, z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
C9—H9A···O1iii | 0.93 | 2.41 | 3.279 (8) | 155 |
C2—H2C···O3iv | 0.93 | 2.48 | 3.395 (9) | 170 |
Symmetry codes: (iii) −x+1/2, y−1/2, z−1/2; (iv) −x+3/2, y−1/2, z+1/2. |