metal-organic compounds
Diaquadimethanolbis[4-(1H-tetrazol-1-yl)benzoato]zinc(II) dihydrate
aDepartment of Chemistry, Nankai University, Tianjin 300071, People's Republic of China, and School of Chemical Engineering and Technology, Hebei University of Technology, Tianjin 300130, People's Republic of China
*Correspondence e-mail: zsmchange@sina.com
In the title compound, [Zn(C8H5N4O2)2(CH3OH)2(H2O)2]·2H2O, the ZnII ion lies on an inversion centre and is coordinated by two O atoms from two 4-(tetrazol-1-yl)benzoate ligands, two O atoms from two methanol molecules and two O atoms from two water molecules in a slightly distorted octahedral geometry. In addition, there are two uncoordinated water molecules in the The is stabilized by intermolecular O—H⋯O hydrogen bonds.
Related literature
For related literature, see: Zou et al. (2005); Dinca et al. (2006); Li et al. (2007); Zhang & Du (2007).
Experimental
Crystal data
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Refinement
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Data collection: SMART (Bruker, 1998); cell SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536808008490/at2552sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536808008490/at2552Isup2.hkl
A solution of Zn(NO3)2.6H2O (0.1 mmol) in water (5 ml) was added to a solution of 4-(tetrazol-1-yl) benzoic acid (38 mg, 0.2 mmol) and sodium hydroxide (8 mg, 0.2 mmol) in methanol (5 mL). The reaction mixture was stirred for 30 min and then filtered. Colourless crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation after two weeks [yield: 46%].
H atoms of C were included in calculated positions and treated in the subsequent
as riding atoms, with C—H = 0.93 and 0.96 Å and Uiso(H) = 1.2 and 1.5 Ueq(C,N). The H atoms of water was located in Fourier difference map and refined without restraint.Data collection: SMART (Bruker, 1998); cell
SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).[Zn(C8H5N4O2)2(CH4O)2(H2O)2]·2H2O | F(000) = 600 |
Mr = 579.84 | Dx = 1.611 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 11248 reflections |
a = 13.220 (3) Å | θ = 3.1–27.6° |
b = 7.1551 (14) Å | µ = 1.10 mm−1 |
c = 12.636 (3) Å | T = 293 K |
β = 90.24 (3)° | Block, colourless |
V = 1195.3 (4) Å3 | 0.20 × 0.18 × 0.16 mm |
Z = 2 |
Bruker P4 diffractometer | 2746 independent reflections |
Radiation source: fine-focus sealed tube | 2359 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.045 |
ω scans | θmax = 27.5°, θmin = 3.1° |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | h = −17→17 |
Tmin = 0.810, Tmax = 0.844 | k = −9→9 |
12254 measured reflections | l = −16→16 |
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)] = 0.032 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.076 | w = 1/[σ2(Fo2) + (0.0297P)2 + 0.5826P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
2746 reflections | Δρmax = 0.29 e Å−3 |
188 parameters | Δρmin = −0.23 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0228 (12) |
[Zn(C8H5N4O2)2(CH4O)2(H2O)2]·2H2O | V = 1195.3 (4) Å3 |
Mr = 579.84 | Z = 2 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.220 (3) Å | µ = 1.10 mm−1 |
b = 7.1551 (14) Å | T = 293 K |
c = 12.636 (3) Å | 0.20 × 0.18 × 0.16 mm |
β = 90.24 (3)° |
Bruker P4 diffractometer | 2746 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 1998) | 2359 reflections with I > 2σ(I) |
Tmin = 0.810, Tmax = 0.844 | Rint = 0.045 |
12254 measured reflections |
R[F2 > 2σ(F2)] = 0.032 | 0 restraints |
wR(F2) = 0.076 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 0.29 e Å−3 |
2746 reflections | Δρmin = −0.23 e Å−3 |
188 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Zn1 | 0.5000 | 0.0000 | 1.0000 | 0.02298 (11) | |
O1 | 0.63696 (9) | 0.0452 (2) | 0.92928 (10) | 0.0313 (3) | |
O2 | 0.73211 (10) | 0.1468 (2) | 1.06367 (10) | 0.0399 (4) | |
C2 | 0.97854 (12) | 0.0991 (2) | 0.77039 (14) | 0.0231 (4) | |
N4 | 1.06694 (11) | 0.0940 (2) | 0.70586 (12) | 0.0243 (3) | |
C5 | 0.80990 (13) | 0.1028 (2) | 0.89760 (14) | 0.0228 (4) | |
N3 | 1.06465 (12) | 0.1453 (3) | 0.60316 (13) | 0.0339 (4) | |
C4 | 0.90418 (13) | 0.1480 (3) | 0.93867 (14) | 0.0259 (4) | |
H4 | 0.9104 | 0.1793 | 1.0098 | 0.031* | |
N1 | 1.21854 (12) | 0.0669 (3) | 0.64661 (14) | 0.0342 (4) | |
C7 | 0.88492 (14) | 0.0580 (3) | 0.72624 (15) | 0.0282 (4) | |
H7 | 0.8786 | 0.0294 | 0.6547 | 0.034* | |
C3 | 0.98863 (14) | 0.1470 (3) | 0.87560 (15) | 0.0274 (4) | |
H3 | 1.0516 | 0.1782 | 0.9035 | 0.033* | |
C8 | 0.71954 (13) | 0.0989 (3) | 0.96960 (14) | 0.0256 (4) | |
C1 | 1.16184 (14) | 0.0462 (3) | 0.72993 (16) | 0.0291 (4) | |
H1 | 1.1840 | 0.0047 | 0.7958 | 0.035* | |
C6 | 0.80137 (14) | 0.0608 (3) | 0.79125 (15) | 0.0279 (4) | |
H6 | 0.7380 | 0.0339 | 0.7629 | 0.033* | |
N2 | 1.15560 (13) | 0.1290 (3) | 0.56869 (14) | 0.0375 (4) | |
O3 | 0.54347 (11) | −0.2616 (2) | 1.06193 (13) | 0.0380 (4) | |
C9 | 0.63908 (16) | −0.3252 (3) | 1.0949 (2) | 0.0470 (6) | |
H9A | 0.6907 | −0.2579 | 1.0578 | 0.071* | |
H9B | 0.6451 | −0.4563 | 1.0799 | 0.071* | |
H9C | 0.6467 | −0.3050 | 1.1696 | 0.071* | |
O2W | 0.43377 (14) | 0.4734 (2) | 0.16558 (13) | 0.0340 (3) | |
O1W | 0.54904 (11) | 0.14327 (19) | 1.13919 (10) | 0.0289 (3) | |
H1WA | 0.5471 | 0.0718 | 1.1898 | 0.043* | |
H2WA | 0.378 (2) | 0.457 (4) | 0.156 (2) | 0.053 (9)* | |
H2WB | 0.463 (2) | 0.382 (4) | 0.156 (2) | 0.061 (10)* | |
H1WB | 0.612 (2) | 0.155 (4) | 1.121 (2) | 0.058 (8)* | |
H3M | 0.5060 (19) | −0.325 (4) | 1.088 (2) | 0.047 (8)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.01705 (16) | 0.02848 (18) | 0.02340 (17) | 0.00002 (12) | −0.00056 (11) | 0.00133 (13) |
O1 | 0.0173 (6) | 0.0487 (9) | 0.0279 (7) | −0.0049 (6) | 0.0003 (5) | 0.0000 (6) |
O2 | 0.0265 (7) | 0.0670 (11) | 0.0261 (7) | −0.0095 (7) | 0.0019 (6) | −0.0061 (7) |
C2 | 0.0174 (9) | 0.0241 (9) | 0.0279 (9) | −0.0001 (7) | 0.0021 (7) | 0.0030 (7) |
N4 | 0.0191 (7) | 0.0275 (8) | 0.0261 (8) | 0.0008 (6) | −0.0003 (6) | 0.0027 (7) |
C5 | 0.0184 (8) | 0.0231 (9) | 0.0270 (9) | −0.0014 (7) | 0.0000 (7) | 0.0016 (7) |
N3 | 0.0277 (9) | 0.0455 (10) | 0.0284 (9) | 0.0043 (7) | 0.0021 (7) | 0.0072 (8) |
C4 | 0.0240 (9) | 0.0310 (10) | 0.0227 (9) | −0.0040 (7) | −0.0023 (7) | 0.0004 (8) |
N1 | 0.0239 (9) | 0.0384 (9) | 0.0403 (10) | 0.0029 (7) | 0.0040 (7) | 0.0031 (8) |
C7 | 0.0244 (9) | 0.0352 (10) | 0.0249 (9) | −0.0018 (8) | −0.0025 (8) | −0.0039 (8) |
C3 | 0.0190 (9) | 0.0330 (10) | 0.0301 (10) | −0.0040 (7) | −0.0053 (7) | 0.0009 (8) |
C8 | 0.0199 (9) | 0.0283 (10) | 0.0287 (10) | −0.0013 (7) | −0.0004 (7) | 0.0038 (8) |
C1 | 0.0214 (9) | 0.0331 (11) | 0.0328 (10) | 0.0023 (7) | −0.0020 (8) | 0.0010 (8) |
C6 | 0.0179 (9) | 0.0362 (10) | 0.0294 (10) | −0.0033 (7) | −0.0039 (7) | −0.0030 (8) |
N2 | 0.0290 (9) | 0.0478 (11) | 0.0358 (10) | 0.0035 (8) | 0.0080 (7) | 0.0093 (8) |
O3 | 0.0261 (7) | 0.0373 (9) | 0.0505 (9) | 0.0028 (7) | −0.0007 (7) | 0.0194 (7) |
C9 | 0.0323 (12) | 0.0468 (14) | 0.0620 (15) | 0.0093 (10) | −0.0041 (11) | 0.0120 (12) |
O2W | 0.0277 (8) | 0.0361 (9) | 0.0382 (8) | −0.0020 (7) | 0.0031 (7) | −0.0057 (7) |
O1W | 0.0251 (7) | 0.0359 (8) | 0.0257 (7) | 0.0002 (6) | 0.0004 (6) | 0.0029 (6) |
Zn1—O1 | 2.0483 (14) | C4—H4 | 0.9300 |
Zn1—O1i | 2.0483 (14) | N1—C1 | 1.304 (3) |
Zn1—O3 | 2.1078 (15) | N1—N2 | 1.361 (2) |
Zn1—O3i | 2.1078 (15) | C7—C6 | 1.379 (3) |
Zn1—O1Wi | 2.1342 (14) | C7—H7 | 0.9300 |
Zn1—O1W | 2.1342 (14) | C3—H3 | 0.9300 |
O1—C8 | 1.263 (2) | C1—H1 | 0.9300 |
O2—C8 | 1.247 (2) | C6—H6 | 0.9300 |
C2—C3 | 1.379 (3) | O3—C9 | 1.405 (2) |
C2—C7 | 1.387 (2) | O3—H3M | 0.75 (3) |
C2—N4 | 1.428 (2) | C9—H9A | 0.9600 |
N4—C1 | 1.334 (2) | C9—H9B | 0.9600 |
N4—N3 | 1.349 (2) | C9—H9C | 0.9600 |
C5—C6 | 1.381 (3) | O2W—H2WA | 0.75 (3) |
C5—C4 | 1.386 (2) | O2W—H2WB | 0.77 (3) |
C5—C8 | 1.505 (2) | O1W—H1WA | 0.8200 |
N3—N2 | 1.286 (2) | O1W—H1WB | 0.87 (3) |
C4—C3 | 1.375 (3) | ||
O1—Zn1—O1i | 180.00 (3) | C6—C7—C2 | 118.22 (17) |
O1—Zn1—O3 | 93.56 (6) | C6—C7—H7 | 120.9 |
O1i—Zn1—O3 | 86.44 (6) | C2—C7—H7 | 120.9 |
O1—Zn1—O3i | 86.44 (6) | C4—C3—C2 | 119.00 (17) |
O1i—Zn1—O3i | 93.56 (6) | C4—C3—H3 | 120.5 |
O3—Zn1—O3i | 180.0 | C2—C3—H3 | 120.5 |
O1—Zn1—O1Wi | 88.98 (6) | O2—C8—O1 | 125.41 (17) |
O1i—Zn1—O1Wi | 91.02 (6) | O2—C8—C5 | 117.92 (16) |
O3—Zn1—O1Wi | 87.75 (6) | O1—C8—C5 | 116.66 (16) |
O3i—Zn1—O1Wi | 92.25 (6) | N1—C1—N4 | 109.28 (17) |
O1—Zn1—O1W | 91.02 (6) | N1—C1—H1 | 125.4 |
O1i—Zn1—O1W | 88.98 (6) | N4—C1—H1 | 125.4 |
O3—Zn1—O1W | 92.25 (6) | C7—C6—C5 | 121.35 (17) |
O3i—Zn1—O1W | 87.75 (6) | C7—C6—H6 | 119.3 |
O1Wi—Zn1—O1W | 180.0 | C5—C6—H6 | 119.3 |
C8—O1—Zn1 | 129.52 (12) | N3—N2—N1 | 110.75 (16) |
C3—C2—C7 | 121.54 (17) | C9—O3—Zn1 | 129.90 (14) |
C3—C2—N4 | 118.74 (16) | C9—O3—H3M | 105 (2) |
C7—C2—N4 | 119.72 (16) | Zn1—O3—H3M | 122 (2) |
C1—N4—N3 | 107.84 (15) | O3—C9—H9A | 109.5 |
C1—N4—C2 | 130.34 (16) | O3—C9—H9B | 109.5 |
N3—N4—C2 | 121.81 (15) | H9A—C9—H9B | 109.5 |
C6—C5—C4 | 118.98 (17) | O3—C9—H9C | 109.5 |
C6—C5—C8 | 121.50 (16) | H9A—C9—H9C | 109.5 |
C4—C5—C8 | 119.52 (16) | H9B—C9—H9C | 109.5 |
N2—N3—N4 | 106.50 (15) | H2WA—O2W—H2WB | 109 (3) |
C3—C4—C5 | 120.86 (17) | Zn1—O1W—H1WA | 109.5 |
C3—C4—H4 | 119.6 | Zn1—O1W—H1WB | 96.5 (17) |
C5—C4—H4 | 119.6 | H1WA—O1W—H1WB | 107.7 |
C1—N1—N2 | 105.63 (15) | ||
O1i—Zn1—O1—C8 | 73 (100) | Zn1—O1—C8—C5 | 174.81 (12) |
O3—Zn1—O1—C8 | −78.56 (17) | C6—C5—C8—O2 | −176.77 (19) |
O3i—Zn1—O1—C8 | 101.44 (17) | C4—C5—C8—O2 | 3.7 (3) |
O1Wi—Zn1—O1—C8 | −166.24 (17) | C6—C5—C8—O1 | 3.9 (3) |
O1W—Zn1—O1—C8 | 13.76 (17) | C4—C5—C8—O1 | −175.56 (17) |
C3—C2—N4—C1 | 33.9 (3) | N2—N1—C1—N4 | −0.2 (2) |
C7—C2—N4—C1 | −146.7 (2) | N3—N4—C1—N1 | 0.4 (2) |
C3—C2—N4—N3 | −144.73 (19) | C2—N4—C1—N1 | −178.39 (18) |
C7—C2—N4—N3 | 34.7 (3) | C2—C7—C6—C5 | −0.2 (3) |
C1—N4—N3—N2 | −0.4 (2) | C4—C5—C6—C7 | 1.8 (3) |
C2—N4—N3—N2 | 178.53 (17) | C8—C5—C6—C7 | −177.68 (18) |
C6—C5—C4—C3 | −1.5 (3) | N4—N3—N2—N1 | 0.2 (2) |
C8—C5—C4—C3 | 177.97 (17) | C1—N1—N2—N3 | 0.0 (2) |
C3—C2—C7—C6 | −1.8 (3) | O1—Zn1—O3—C9 | 31.19 (19) |
N4—C2—C7—C6 | 178.77 (17) | O1i—Zn1—O3—C9 | −148.81 (19) |
C5—C4—C3—C2 | −0.4 (3) | O3i—Zn1—O3—C9 | −165 (73) |
C7—C2—C3—C4 | 2.1 (3) | O1Wi—Zn1—O3—C9 | 120.04 (19) |
N4—C2—C3—C4 | −178.49 (17) | O1W—Zn1—O3—C9 | −59.96 (19) |
Zn1—O1—C8—O2 | −4.4 (3) |
Symmetry code: (i) −x+1, −y, −z+2. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1WA···O2Wii | 0.82 | 1.97 | 2.759 (2) | 160 |
O2W—H2WB···O1Wiii | 0.77 (3) | 2.07 (3) | 2.831 (2) | 175 (3) |
O3—H3M···O2Wiv | 0.75 (3) | 1.99 (3) | 2.726 (2) | 167 (3) |
Symmetry codes: (ii) −x+1, y−1/2, −z+3/2; (iii) x, y, z−1; (iv) x, y−1, z+1. |
Experimental details
Crystal data | |
Chemical formula | [Zn(C8H5N4O2)2(CH4O)2(H2O)2]·2H2O |
Mr | 579.84 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 13.220 (3), 7.1551 (14), 12.636 (3) |
β (°) | 90.24 (3) |
V (Å3) | 1195.3 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.10 |
Crystal size (mm) | 0.20 × 0.18 × 0.16 |
Data collection | |
Diffractometer | Bruker P4 diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 1998) |
Tmin, Tmax | 0.810, 0.844 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12254, 2746, 2359 |
Rint | 0.045 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.076, 1.04 |
No. of reflections | 2746 |
No. of parameters | 188 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.29, −0.23 |
Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
Zn1—O1 | 2.0483 (14) | Zn1—O1W | 2.1342 (14) |
Zn1—O3 | 2.1078 (15) | ||
O1—Zn1—O3 | 93.56 (6) | O3—Zn1—O1W | 92.25 (6) |
O1—Zn1—O1W | 91.02 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1W—H1WA···O2Wi | 0.82 | 1.97 | 2.759 (2) | 160.3 |
O2W—H2WB···O1Wii | 0.77 (3) | 2.07 (3) | 2.831 (2) | 175 (3) |
O3—H3M···O2Wiii | 0.75 (3) | 1.99 (3) | 2.726 (2) | 167 (3) |
Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x, y, z−1; (iii) x, y−1, z+1. |
Acknowledgements
The authors thank the Natural Science Foundation of Tianjin, China (No. 07JCZDJC00500) for financial support.
References
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Coordination architectures formed from 1H-tetrazol and its derivatives have attracted wide attentions in recent years, due to not only their fascinating structures and topologies, but also their potential applications in luminescence, magnetism and gas storage (Dinca, et al., 2006; Li, et al., 2007). However, there are rare reports (Zou, et al., 2005) of the coordination systems using the benzoic acids with N-heterocycle as ligands. So we synthesized several coordination compounds by such ligands. And here we report the structure of title compound (I).
The structure of (I) consists of discrete neutral unit [Zn(C8H5N4O2)2(CH3OH)2(H2O)2], and two lattice water molecules (Fig. 1), atom Zn1 lies on an inversion centre and is coordinated by two O atoms from two 4-(tetrazol-1-yl) benzoate ligands, two O atoms from two methanol molecules and two O atoms from two water molecules in a distorted octahedral geometry.The metal ion of (I) is bonded to the carboxyl group of 4-(tetrazol-1-yl) benzoate, which is remarkably different from our previous reported compound that using the same ligand with N donor coordinating to metal ion (Zhang et al., 2007). The crystal stacking of (I) (Fig. 2) is stabilized by the intermolecular O—H···O hydrogen bonds (Table 2).