catena-Poly[[(2,2′-bipyridine-κ²N,N′)zinc(II)]-μ-oxalato]

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.

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

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Computing details

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]

Crystal data

[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) Å^3	Needle, brown
Z = 4	0.41 × 0.06 × 0.03 mm

Data collection

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

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.023	H-atom parameters constrained
wR(F^2) = 0.021	w = 1/[σ^2(Fo^2) + (0.001P)^2 + 0.0046P] where P = (Fo^2 + 2Fc^2)/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

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 (Ų)

	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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Zn1—O4^i	2.080 (3)	C1—H1C	0.9300
Zn1—O2	2.094 (3)	C2—C3	1.361 (9)
Zn1—O3^i	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—Zn1^ii	2.107 (4)	C9—H9A	0.9300
O4—C11	1.247 (5)	C10—H10A	0.9300
O4—Zn1^ii	2.080 (3)	C11—C12	1.556 (4)
C1—C2	1.360 (8)
O4^i—Zn1—O2	163.93 (9)	C4—C3—C2	117.4 (7)
O4^i—Zn1—O3^i	78.96 (15)	C4—C3—H3A	121.3
O2—Zn1—O3^i	90.66 (16)	C2—C3—H3A	121.3
O4^i—Zn1—O1	88.90 (16)	C3—C4—C5	122.2 (7)
O2—Zn1—O1	79.72 (16)	C3—C4—H4A	118.9
O3^i—Zn1—O1	94.92 (13)	C5—C4—H4A	118.9
O4^i—Zn1—N1	94.92 (15)	N1—C5—C4	118.5 (7)
O2—Zn1—N1	97.26 (16)	N1—C5—C6	116.2 (7)
O3^i—Zn1—N1	168.48 (17)	C4—C5—C6	125.3 (7)
O1—Zn1—N1	94.71 (19)	N2—C6—C7	123.8 (7)
O4^i—Zn1—N2	98.68 (15)	N2—C6—C5	115.1 (7)
O2—Zn1—N2	94.31 (15)	C7—C6—C5	121.1 (7)
O3^i—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—Zn1^ii	113.5 (4)	C9—C10—H10A	118.9
C11—O4—Zn1^ii	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
O4^i—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)
O3^i—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)
O4^i—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)
O3^i—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)
O4^i—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)
O3^i—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)
O4^i—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)
O3^i—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)
O4^i—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)
O3^i—Zn1—O1—C11	−86.0 (4)	Zn1^ii—O4—C11—O1	−179.9 (4)
N1—Zn1—O1—C11	100.4 (4)	Zn1^ii—O4—C11—C12	−1.2 (4)
N2—Zn1—O1—C11	62.1 (12)	Zn1—O1—C11—O4	174.9 (4)
O4^i—Zn1—O2—C12	42.2 (8)	Zn1—O1—C11—C12	−3.7 (5)
O3^i—Zn1—O2—C12	91.5 (4)	Zn1^ii—O3—C12—O2	178.1 (5)
O1—Zn1—O2—C12	−3.4 (4)	Zn1^ii—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)

D—H···A	D—H	H···A	D···A	D—H···A
C9—H9A···O1^iii	0.93	2.41	3.279 (8)	155
C2—H2C···O3^iv	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.