Related literature
A pseudo-polymorph of the title compound containing a solvent water molecule exists in a P2/c modification, which features zinc in an unambiguous tetrahedral coordination geometry; see Deng et al. (2006
).
Experimental
Crystal data
[Zn(C8H5O3)2(H2O)2] Mr = 399.64 Monoclinic, C 2/c a = 27.537 (1) Å b = 5.0039 (2) Å c = 12.0930 (6) Å β = 110.039 (2)° V = 1565.4 (1) Å3 Z = 4 Mo Kα radiation μ = 1.61 mm−1 T = 295 (2) K 0.34 × 0.26 × 0.18 mm
|
Data collection
Rigaku R-AXIS RAPID diffractometer Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) Tmin = 0.532, Tmax = 0.760 7203 measured reflections 1785 independent reflections 1448 reflections with I > 2σ(I) Rint = 0.034
|
Zn1—O1W | 1.983 (2) | Zn1—O1 | 2.005 (2) | Zn1—O2 | 2.512 (2) | | |
D—H⋯A | D—H | H⋯A | D⋯A | D—H⋯A | O1W—H1W1⋯O1i | 0.84 (1) | 1.93 (1) | 2.761 (2) | 174 (3) | O1W—H1W2⋯O2ii | 0.84 (1) | 1.88 (1) | 2.720 (2) | 174 (3) | Symmetry codes: (i) ; (ii) -x+1, -y, -z+1. | |
Data collection: RAPID-AUTO (Rigaku, 1998
); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002
); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008
); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008
); molecular graphics: X-SEED (Barbour, 2001
); software used to prepare material for publication: publCIF (Westrip, 2008
).
Supporting information
Zinc diacetate dihydrate (2.2 g, 10 mmol) was added to anaqueous solution of 4-formylbenzoic acid (3.0 g, 20 mmol) that has earlier been treated with 1 ml pyridine to give a pH of 6. The solution was allowed to evaporate at room temperature; colorless prismatic crystals separated from the filtered solution after several days. C&N elemental analysis. Calc. C16H14O8Zn: C 48.08, H3.53%. Found: C 48.06, H 3.56%.
The formyl group is disordered over two sites; the ratio of the site occupation factors refined to a 0.508 (5):0.492 (5) ratio.
The carbon-bound H atoms were placed in calculated positions [C–H 0.93 Å and Uiso(H) 1.2Ueq(C)], and were included in the refinement in the riding-model approximation. The water H-atoms were located in a difference Fourier map, and were refined with distance restraints of O–H 0.85±0.01 Å and H···H 1.39±0.01 Å; their displacement parameters were freely refined.
Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2008).
Diaquabis(4-formylbenzoato-
κO)zinc(II)
top Crystal data top [Zn(C8H5O3)2(H2O)2] | F(000) = 816 |
Mr = 399.64 | Dx = 1.696 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 5776 reflections |
a = 27.537 (1) Å | θ = 3.2–27.5° |
b = 5.0039 (2) Å | µ = 1.61 mm−1 |
c = 12.0930 (6) Å | T = 295 K |
β = 110.039 (2)° | Block, colorless |
V = 1565.4 (1) Å3 | 0.34 × 0.26 × 0.18 mm |
Z = 4 | |
Data collection top Rigaku R-AXIS RAPID diffractometer | 1785 independent reflections |
Radiation source: fine-focus sealed tube | 1448 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
Detector resolution: 10.000 pixels mm-1 | θmax = 27.5°, θmin = 3.2° |
ω scans | h = −35→35 |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | k = −6→6 |
Tmin = 0.532, Tmax = 0.760 | l = −15→15 |
7203 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)] = 0.029 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.082 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | w = 1/[σ2(Fo2) + (0.0444P)2 + 0.5739P] where P = (Fo2 + 2Fc2)/3 |
1785 reflections | (Δ/σ)max = 0.001 |
132 parameters | Δρmax = 0.59 e Å−3 |
3 restraints | Δρmin = −0.38 e Å−3 |
Crystal data top [Zn(C8H5O3)2(H2O)2] | V = 1565.4 (1) Å3 |
Mr = 399.64 | Z = 4 |
Monoclinic, C2/c | Mo Kα radiation |
a = 27.537 (1) Å | µ = 1.61 mm−1 |
b = 5.0039 (2) Å | T = 295 K |
c = 12.0930 (6) Å | 0.34 × 0.26 × 0.18 mm |
β = 110.039 (2)° | |
Data collection top Rigaku R-AXIS RAPID diffractometer | 1785 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 1448 reflections with I > 2σ(I) |
Tmin = 0.532, Tmax = 0.760 | Rint = 0.034 |
7203 measured reflections | |
Refinement top R[F2 > 2σ(F2)] = 0.029 | 3 restraints |
wR(F2) = 0.082 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.09 | Δρmax = 0.59 e Å−3 |
1785 reflections | Δρmin = −0.38 e Å−3 |
132 parameters | |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | Occ. (<1) |
Zn1 | 0.5000 | 0.07300 (7) | 0.7500 | 0.03500 (15) | |
O1W | 0.52887 (7) | −0.2045 (3) | 0.67306 (15) | 0.0420 (4) | |
O1 | 0.44080 (6) | 0.3312 (3) | 0.69827 (13) | 0.0347 (4) | |
O2 | 0.46297 (6) | 0.2522 (3) | 0.54394 (14) | 0.0396 (4) | |
O3 | 0.28940 (13) | 1.2782 (7) | 0.2481 (3) | 0.0537 (13) | 0.508 (5) |
O3' | 0.25060 (16) | 1.2320 (10) | 0.3707 (4) | 0.0757 (18) | 0.492 (5) |
H1W1 | 0.5398 (10) | −0.346 (3) | 0.7104 (19) | 0.051 (8)* | |
H1W2 | 0.5313 (11) | −0.208 (5) | 0.6055 (12) | 0.062 (9)* | |
C1 | 0.43534 (8) | 0.3714 (4) | 0.59025 (19) | 0.0299 (5) | |
C2 | 0.39595 (8) | 0.5736 (4) | 0.52428 (18) | 0.0283 (4) | |
C3 | 0.35743 (9) | 0.6552 (5) | 0.5675 (2) | 0.0396 (5) | |
H3 | 0.3554 | 0.5809 | 0.6363 | 0.048* | |
C4 | 0.32199 (9) | 0.8489 (6) | 0.5070 (2) | 0.0444 (6) | |
H4 | 0.2963 | 0.9046 | 0.5357 | 0.053* | |
C5 | 0.32469 (8) | 0.9588 (4) | 0.4047 (2) | 0.0348 (5) | |
C6 | 0.36283 (9) | 0.8759 (5) | 0.3612 (2) | 0.0373 (5) | |
H6 | 0.3645 | 0.9485 | 0.2919 | 0.045* | |
C7 | 0.39830 (9) | 0.6846 (5) | 0.4219 (2) | 0.0358 (5) | |
H7 | 0.4240 | 0.6303 | 0.3932 | 0.043* | |
C8 | 0.28767 (9) | 1.1697 (5) | 0.3399 (2) | 0.0460 (6) | |
H8 | 0.2621 | 1.2233 | 0.3691 | 0.055* | 0.508 (5) |
H8' | 0.2924 | 1.2551 | 0.2760 | 0.055* | 0.492 (5) |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Zn1 | 0.0384 (2) | 0.02089 (19) | 0.0487 (3) | 0.000 | 0.01878 (17) | 0.000 |
O1W | 0.0676 (11) | 0.0278 (8) | 0.0359 (10) | 0.0119 (8) | 0.0247 (8) | 0.0052 (7) |
O1 | 0.0445 (9) | 0.0313 (8) | 0.0266 (8) | −0.0005 (7) | 0.0101 (6) | 0.0054 (6) |
O2 | 0.0460 (9) | 0.0351 (8) | 0.0355 (9) | 0.0121 (7) | 0.0111 (7) | −0.0003 (7) |
O3 | 0.051 (2) | 0.055 (2) | 0.052 (2) | 0.0156 (17) | 0.0141 (17) | 0.0215 (19) |
O3' | 0.058 (3) | 0.086 (4) | 0.079 (3) | 0.036 (2) | 0.019 (2) | 0.008 (3) |
C1 | 0.0335 (11) | 0.0244 (10) | 0.0276 (11) | −0.0051 (8) | 0.0051 (8) | −0.0011 (8) |
C2 | 0.0318 (10) | 0.0251 (10) | 0.0264 (10) | −0.0022 (8) | 0.0078 (8) | −0.0022 (9) |
C3 | 0.0413 (12) | 0.0478 (13) | 0.0338 (13) | 0.0033 (11) | 0.0180 (10) | 0.0055 (10) |
C4 | 0.0356 (12) | 0.0557 (15) | 0.0458 (15) | 0.0093 (11) | 0.0190 (10) | −0.0025 (12) |
C5 | 0.0314 (11) | 0.0341 (12) | 0.0337 (12) | 0.0016 (9) | 0.0044 (9) | −0.0032 (10) |
C6 | 0.0418 (12) | 0.0386 (12) | 0.0322 (12) | 0.0061 (10) | 0.0135 (9) | 0.0093 (10) |
C7 | 0.0417 (12) | 0.0366 (11) | 0.0342 (12) | 0.0106 (10) | 0.0196 (10) | 0.0037 (10) |
C8 | 0.0368 (13) | 0.0432 (13) | 0.0497 (16) | 0.0091 (11) | 0.0043 (11) | −0.0036 (12) |
Geometric parameters (Å, º) top Zn1—O1w | 1.983 (2) | C2—C3 | 1.395 (3) |
Zn1—O1wi | 1.983 (2) | C3—C4 | 1.392 (4) |
Zn1—O1i | 2.005 (2) | C3—H3 | 0.9300 |
Zn1—O1 | 2.005 (2) | C4—C5 | 1.379 (4) |
Zn1—O2 | 2.512 (2) | C4—H4 | 0.9300 |
O1W—H1W1 | 0.84 (1) | C5—C6 | 1.389 (3) |
O1W—H1W2 | 0.84 (1) | C5—C8 | 1.490 (3) |
O1—C1 | 1.279 (3) | C6—C7 | 1.385 (3) |
O2—C1 | 1.241 (3) | C6—H6 | 0.9300 |
O3—C8 | 1.251 (4) | C7—H7 | 0.9300 |
O3'—C8 | 1.240 (5) | C8—H8 | 0.9300 |
C1—C2 | 1.498 (3) | C8—H8' | 0.9300 |
C2—C7 | 1.379 (3) | | |
| | | |
O1W—Zn1—O1Wi | 91.11 (10) | C5—C4—H4 | 119.8 |
O1W—Zn1—O1i | 100.59 (7) | C3—C4—H4 | 119.8 |
O1Wi—Zn1—O1i | 135.95 (7) | C4—C5—C6 | 120.0 (2) |
O1W—Zn1—O1 | 135.95 (7) | C4—C5—C8 | 121.1 (2) |
O1Wi—Zn1—O1 | 100.59 (7) | C6—C5—C8 | 118.9 (2) |
O1i—Zn1—O1 | 99.75 (9) | C7—C6—C5 | 119.6 (2) |
Zn1—O1W—H1W1 | 117.8 (17) | C7—C6—H6 | 120.2 |
Zn1—O1W—H1W2 | 130.4 (17) | C5—C6—H6 | 120.2 |
H1W1—O1W—H1W2 | 111.8 (16) | C2—C7—C6 | 120.8 (2) |
C1—O1—Zn1 | 102.62 (13) | C2—C7—H7 | 119.6 |
O2—C1—O1 | 120.65 (19) | C6—C7—H7 | 119.6 |
O2—C1—C2 | 121.9 (2) | O3—C8—O3' | 116.3 (3) |
O1—C1—C2 | 117.42 (19) | O3—C8—C5 | 123.1 (3) |
C7—C2—C3 | 119.6 (2) | O3'—C8—C5 | 120.4 (3) |
C7—C2—C1 | 120.14 (19) | O3—C8—H8 | 118.4 |
C3—C2—C1 | 120.2 (2) | C5—C8—H8 | 118.4 |
C4—C3—C2 | 119.5 (2) | O3'—C8—H8' | 119.8 |
C4—C3—H3 | 120.2 | C5—C8—H8' | 119.8 |
C2—C3—H3 | 120.2 | H8—C8—H8' | 121.5 |
C5—C4—C3 | 120.4 (2) | | |
| | | |
O1W—Zn1—O1—C1 | −27.75 (17) | C3—C4—C5—C6 | 0.1 (4) |
O1Wi—Zn1—O1—C1 | −130.56 (13) | C3—C4—C5—C8 | −178.9 (2) |
O1i—Zn1—O1—C1 | 88.73 (13) | C4—C5—C6—C7 | −0.6 (4) |
Zn1—O1—C1—O2 | 2.0 (2) | C8—C5—C6—C7 | 178.5 (2) |
Zn1—O1—C1—C2 | −175.83 (14) | C3—C2—C7—C6 | −0.1 (3) |
O2—C1—C2—C7 | −17.2 (3) | C1—C2—C7—C6 | −178.6 (2) |
O1—C1—C2—C7 | 160.7 (2) | C5—C6—C7—C2 | 0.6 (4) |
O2—C1—C2—C3 | 164.4 (2) | C4—C5—C8—O3 | 178.6 (3) |
O1—C1—C2—C3 | −17.8 (3) | C6—C5—C8—O3 | −0.5 (4) |
C7—C2—C3—C4 | −0.3 (4) | C4—C5—C8—O3' | −7.0 (5) |
C1—C2—C3—C4 | 178.2 (2) | C6—C5—C8—O3' | 173.9 (3) |
C2—C3—C4—C5 | 0.3 (4) | | |
Symmetry code: (i) −x+1, y, −z+3/2. |
Hydrogen-bond geometry (Å, º) top D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···O1ii | 0.84 (1) | 1.93 (1) | 2.761 (2) | 174 (3) |
O1W—H1W2···O2iii | 0.84 (1) | 1.88 (1) | 2.720 (2) | 174 (3) |
Symmetry codes: (ii) −x+1, y−1, −z+3/2; (iii) −x+1, −y, −z+1. |
Experimental details
Crystal data |
Chemical formula | [Zn(C8H5O3)2(H2O)2] |
Mr | 399.64 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 295 |
a, b, c (Å) | 27.537 (1), 5.0039 (2), 12.0930 (6) |
β (°) | 110.039 (2) |
V (Å3) | 1565.4 (1) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 1.61 |
Crystal size (mm) | 0.34 × 0.26 × 0.18 |
|
Data collection |
Diffractometer | Rigaku R-AXIS RAPID diffractometer |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.532, 0.760 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7203, 1785, 1448 |
Rint | 0.034 |
(sin θ/λ)max (Å−1) | 0.649 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.029, 0.082, 1.09 |
No. of reflections | 1785 |
No. of parameters | 132 |
No. of restraints | 3 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.59, −0.38 |
Selected bond lengths (Å) topZn1—O1w | 1.983 (2) | Zn1—O2 | 2.512 (2) |
Zn1—O1 | 2.005 (2) | | |
Hydrogen-bond geometry (Å, º) top D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1W1···O1i | 0.84 (1) | 1.93 (1) | 2.761 (2) | 174 (3) |
O1W—H1W2···O2ii | 0.84 (1) | 1.88 (1) | 2.720 (2) | 174 (3) |
Symmetry codes: (i) −x+1, y−1, −z+3/2; (ii) −x+1, −y, −z+1. |
Acknowledgements
We thank the Heilongjiang Province Natural Science Foundation (No. B200501), the Scientific Fund for Remarkable Teachers of Heilongjiang Province (No. 1054G036), Heilongjiang University and the University of Malaya for supporting this work.
References
Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Deng, Z.-P., Gao, S., Huo, L.-H. & Zhao, H. (2006). Acta Cryst. E62, m3524–m3526. Web of Science CSD CrossRef IUCr Journals Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalStructure. Rigaku/MSC, The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2008). publCIF. In preparation. Google Scholar
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A pseuodpolymorph of the title compound containing a solvent water molecule was isolated from the reaction of zinc acetate and 4-formylbenzoic acid in the presence of sodium hydroxide (Deng et al., 2006). The reaction with pyridine in place of sodium hydroxide yielded the title polymorph.