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In the title polymeric compound, {[Zn2(C8H4O4)2(H2O)2]·2C4H9NO}n, each of the terephthalate dianions uses both carboxyl­ate ends to bridge a pair of water-coordinated ZnII atoms [Zn...Zn = 2.9527 (4) Å] into a two-dimensional square-grid motif. One of the dianions lies on a special position of site symmetry \overline{1}, whereas the other lies on a general position. Each grid cavity contains two N,N-dimethyl­acetamide mol­ecules.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807060357/ci2501sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807060357/ci2501Isup2.hkl
Contains datablock I

CCDC reference: 672741

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.035
  • wR factor = 0.099
  • Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level B ABSTM02_ALERT_3_B The ratio of expected to reported Tmax/Tmin(RR') is < 0.75 Tmin and Tmax reported: 0.587 1.000 Tmin(prime) and Tmax expected: 0.537 0.589 RR(prime) = 0.643 Please check that your absorption correction is appropriate. PLAT061_ALERT_3_B Tmax/Tmin Range Test RR' too Large ............. 0.62
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.59 PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density .... 2.79 PLAT154_ALERT_1_C The su's on the Cell Angles are Equal (x 10000) 100 Deg. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 4 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.59 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.01 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 4 PLAT731_ALERT_1_C Bond Calc 0.84(3), Rep 0.842(10) ...... 3.00 su-Ra O1W -H1W2 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.84(3), Rep 0.841(10) ...... 3.00 su-Ra O2W -H2W2 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.84(3), Rep 0.840(10) ...... 3.00 su-Ra O1W -H2# 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.84(3), Rep 0.840(10) ...... 3.00 su-Ra O2W -H4# 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 1.90(3), Rep 1.900(10) ...... 3.00 su-Ra H2# -O8 1.555 1.545 PLAT736_ALERT_1_C H...A Calc 2.03(3), Rep 2.030(10) ...... 3.00 su-Ra H4# -O1 1.555 1.655 PLAT764_ALERT_4_C Overcomplete CIF Bond List Detected (Rep/Expd) . 1.11 Ratio
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.589 Tmax scaled 0.589 Tmin scaled 0.345 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 4
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 16 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 8 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 ALERT type 2 Indicator that the structure model may be wrong or deficient 6 ALERT type 3 Indicator that the structure quality may be low 3 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The Cambridge Structural Database (Version 5.28, November 2006; Allen, 2002) lists several examples of zinc terephthalate systems. Some crystallize with DMF-type of solvent molecules. In the present compound, the terephthalate dianion uses both carboxylate ends to bridge a pair of water-coordinated zinc(II) atoms [Zn···Zn = 2.9527 (4) Å] into a two-dimensional square-grid motif (Fig. 1). Each of the grid cavity (Fig. 2) contains two solvent molecules.

Related literature top

The Cambridge Structural Database (Version 5.28, November 2006; Allen, 2002) lists several examples of zinc terephthalate systems. Some crystallize with DMF-type solvent molecules. For the DMF solvate, see: Edgar et al. (2001). For the N,N-diethylformamide solvate, see: Grzesiak et al. (2006).

Experimental top

A mixture of zinc chloride dihydrate (0.5 mmol), terephthalic acid (0.5 mmol) and N,N-dimethylacetamide (12 ml) was heated at 443 K for 3 d. The cooled mixture yielded colourless crystals of the title compound.

Refinement top

H atoms were positioned geometrically (C—H = 0.93–0.96 Å) and refined as riding, with Uiso(H) = 1.2–1.5Ueq(C). The methyl groups were allowed to rotate but not to tip. The water H-atoms were located in a difference Fourier map, and were refined with a distance restraint of O—H = 0.85 (1) Å. The four highest peaks in the final difference Fourier map were observed in the vicinity of the DMA molecules. The positions of the peaks indicate that the DMA molecules are probably not disordered.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2006); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001) and OLEX (Dolomanov et al., 2003); software used to prepare material for publication: publCIF (Westrip, 2007).

Figures top
[Figure 1] Fig. 1. Part of a two-dimensional square-grid motif of the title compound. Displacement ellipsoids are drawn at the 70% probability level, and H atoms as spheres of arbitrary radius. Symmetry code: (i) x + 1, y - 1, z.
[Figure 2] Fig. 2. OLEX (Dolomanov et al., 2003) representation of the square-grid motif.
Poly[[diaquabis(µ2-terephthalato- κ4O:O':O'':O''')dizinc(II)] N,N-dimethylacetamide disolvate] top
Crystal data top
[Zn2(C8H4O4)2(H2O)2]·2C4H9NOZ = 2
Mr = 669.24F(000) = 688
Triclinic, P1Dx = 1.632 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.9291 (5) ÅCell parameters from 3838 reflections
b = 10.0551 (7) Åθ = 2.2–26.0°
c = 20.620 (2) ŵ = 1.83 mm1
α = 78.030 (1)°T = 295 K
β = 81.044 (1)°Block, colourless
γ = 77.266 (1)°0.33 × 0.31 × 0.29 mm
V = 1361.7 (2) Å3
Data collection top
Bruker APEXII area-detector
diffractometer
5269 independent reflections
Radiation source: fine-focus sealed tube4503 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
ϕ and ω scansθmax = 26.0°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 86
Tmin = 0.587, Tmax = 1.000k = 1212
7748 measured reflectionsl = 2525
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.099H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0604P)2 + 0.7539P]
where P = (Fo2 + 2Fc2)/3
5269 reflections(Δ/σ)max = 0.001
383 parametersΔρmax = 1.24 e Å3
4 restraintsΔρmin = 0.44 e Å3
Crystal data top
[Zn2(C8H4O4)2(H2O)2]·2C4H9NOγ = 77.266 (1)°
Mr = 669.24V = 1361.7 (2) Å3
Triclinic, P1Z = 2
a = 6.9291 (5) ÅMo Kα radiation
b = 10.0551 (7) ŵ = 1.83 mm1
c = 20.620 (2) ÅT = 295 K
α = 78.030 (1)°0.33 × 0.31 × 0.29 mm
β = 81.044 (1)°
Data collection top
Bruker APEXII area-detector
diffractometer
5269 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
4503 reflections with I > 2σ(I)
Tmin = 0.587, Tmax = 1.000Rint = 0.016
7748 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0354 restraints
wR(F2) = 0.099H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 1.24 e Å3
5269 reflectionsΔρmin = 0.44 e Å3
383 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Zn10.63480 (4)0.67635 (3)0.719133 (14)0.01316 (10)
Zn20.92767 (4)0.77920 (3)0.775812 (14)0.01324 (10)
O10.5123 (3)0.6234 (2)0.81850 (9)0.0236 (5)
O20.7888 (3)0.6531 (2)0.85183 (9)0.0245 (5)
O30.8096 (3)0.7535 (2)0.63769 (9)0.0250 (5)
O40.9806 (3)0.8735 (2)0.67983 (9)0.0246 (5)
O50.5119 (3)0.8748 (2)0.72861 (11)0.0299 (5)
O60.7024 (3)0.9401 (2)0.78959 (11)0.0309 (5)
O70.1614 (3)1.49770 (19)0.73505 (10)0.0219 (4)
O80.0874 (3)1.59581 (19)0.74699 (10)0.0206 (4)
O90.4592 (4)0.6915 (3)0.54349 (11)0.0450 (7)
O101.0286 (4)0.8186 (3)0.95154 (12)0.0467 (7)
O1W0.4426 (3)0.6272 (2)0.67268 (10)0.0236 (5)
O2W1.1323 (3)0.8078 (2)0.82510 (10)0.0217 (4)
N10.3480 (6)0.7018 (5)0.44740 (18)0.0657 (11)
N21.1224 (6)0.8029 (4)1.05090 (18)0.0602 (10)
C10.6258 (4)0.6158 (3)0.86252 (13)0.0178 (6)
C20.5584 (4)0.5557 (3)0.93373 (13)0.0181 (6)
C30.3839 (4)0.5026 (3)0.94995 (14)0.0226 (6)
H30.30630.50420.91670.027*
C40.3260 (4)0.4472 (3)1.01590 (14)0.0231 (6)
H40.20960.41181.02660.028*
C50.9142 (4)0.8430 (3)0.63250 (13)0.0192 (6)
C60.9616 (4)0.9236 (3)0.56353 (13)0.0201 (6)
C70.8558 (5)0.9188 (3)0.51209 (14)0.0257 (7)
H70.75940.86410.52030.031*
C80.8933 (5)0.9948 (3)0.44886 (14)0.0256 (7)
H80.82180.99150.41480.031*
C90.5516 (4)0.9592 (3)0.75905 (13)0.0199 (6)
C100.4100 (4)1.0962 (3)0.75689 (13)0.0180 (6)
C110.2208 (4)1.1129 (3)0.73742 (14)0.0206 (6)
H110.17961.03820.72740.025*
C120.0946 (4)1.2414 (3)0.73307 (14)0.0192 (6)
H120.03231.25220.72080.023*
C130.1558 (4)1.3544 (3)0.74688 (13)0.0158 (5)
C140.3456 (4)1.3378 (3)0.76604 (14)0.0198 (6)
H140.38781.41280.77530.024*
C150.4704 (4)1.2094 (3)0.77112 (14)0.0200 (6)
H150.59631.19820.78420.024*
C160.0166 (4)1.4929 (3)0.74250 (12)0.0157 (5)
C170.3473 (6)0.6572 (5)0.5108 (2)0.0507 (10)
C180.2010 (6)0.5604 (4)0.54366 (19)0.0452 (9)
H18A0.21920.52930.59000.068*
H18B0.22610.48190.52170.068*
H18C0.06680.60990.53980.068*
C190.4846 (7)0.7971 (5)0.41555 (19)0.0590 (12)
H19A0.53680.82690.44940.088*
H19B0.41330.87620.38830.088*
H19C0.59230.74990.38830.088*
C200.2240 (8)0.6634 (7)0.4052 (2)0.0832 (19)
H20A0.15020.59660.43150.125*
H20B0.30770.62420.36940.125*
H20C0.13300.74440.38700.125*
C211.3211 (6)0.9137 (4)0.9555 (2)0.0496 (10)
H21A1.31780.93950.90810.074*
H21B1.44450.85170.96460.074*
H21C1.30990.99520.97430.074*
C221.1458 (6)0.8407 (4)0.9868 (2)0.0478 (10)
C230.9614 (7)0.7308 (5)1.08110 (19)0.0524 (11)
H23A0.88180.72821.04740.079*
H23B0.88000.77871.11450.079*
H23C1.01600.63791.10140.079*
C241.2542 (9)0.8267 (6)1.0954 (2)0.0812 (17)
H24A1.36400.86331.06900.122*
H24B1.30370.74061.12330.122*
H24C1.18060.89161.12280.122*
H1W10.438 (6)0.652 (4)0.6313 (6)0.041 (11)*
H1W20.329 (3)0.620 (4)0.6927 (18)0.060 (14)*
H2W11.095 (6)0.811 (4)0.8661 (7)0.048 (12)*
H2W21.246 (3)0.757 (3)0.8228 (19)0.050 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Zn10.01266 (17)0.01296 (17)0.01259 (16)0.00214 (12)0.00050 (12)0.00054 (12)
Zn20.01314 (17)0.01313 (17)0.01196 (16)0.00188 (12)0.00091 (12)0.00006 (12)
O10.0223 (11)0.0349 (12)0.0117 (9)0.0074 (9)0.0020 (8)0.0016 (8)
O20.0229 (11)0.0334 (12)0.0158 (10)0.0130 (9)0.0005 (8)0.0049 (8)
O30.0275 (11)0.0304 (12)0.0159 (10)0.0136 (9)0.0000 (8)0.0049 (8)
O40.0368 (12)0.0277 (11)0.0107 (9)0.0144 (10)0.0016 (9)0.0015 (8)
O50.0283 (12)0.0173 (11)0.0415 (13)0.0057 (9)0.0045 (10)0.0099 (9)
O60.0290 (12)0.0245 (11)0.0347 (12)0.0101 (9)0.0097 (10)0.0070 (9)
O70.0157 (10)0.0156 (10)0.0333 (11)0.0009 (8)0.0069 (9)0.0032 (8)
O80.0164 (10)0.0132 (9)0.0313 (11)0.0012 (8)0.0006 (8)0.0051 (8)
O90.0446 (15)0.0735 (19)0.0225 (12)0.0206 (14)0.0096 (11)0.0071 (12)
O100.0457 (16)0.073 (2)0.0252 (12)0.0122 (14)0.0069 (11)0.0158 (12)
O1W0.0185 (11)0.0388 (13)0.0160 (10)0.0122 (9)0.0023 (9)0.0029 (9)
O2W0.0167 (10)0.0306 (12)0.0183 (10)0.0030 (9)0.0021 (8)0.0073 (9)
N10.050 (2)0.104 (3)0.043 (2)0.001 (2)0.0125 (17)0.023 (2)
N20.071 (3)0.069 (3)0.044 (2)0.006 (2)0.0204 (19)0.0154 (18)
C10.0162 (13)0.0167 (13)0.0164 (13)0.0005 (11)0.0011 (11)0.0003 (11)
C20.0203 (14)0.0187 (14)0.0131 (12)0.0052 (11)0.0017 (11)0.0009 (11)
C30.0226 (15)0.0318 (16)0.0141 (13)0.0106 (13)0.0022 (11)0.0002 (12)
C40.0196 (14)0.0309 (16)0.0185 (14)0.0119 (12)0.0002 (11)0.0018 (12)
C50.0206 (14)0.0174 (14)0.0148 (13)0.0017 (11)0.0016 (11)0.0026 (11)
C60.0244 (15)0.0210 (14)0.0131 (13)0.0075 (12)0.0018 (11)0.0014 (11)
C70.0300 (16)0.0296 (16)0.0185 (14)0.0156 (13)0.0019 (12)0.0034 (12)
C80.0318 (17)0.0323 (17)0.0150 (14)0.0162 (14)0.0038 (12)0.0022 (12)
C90.0213 (15)0.0141 (13)0.0178 (13)0.0016 (11)0.0030 (11)0.0025 (11)
C100.0208 (14)0.0150 (13)0.0154 (13)0.0010 (11)0.0002 (11)0.0026 (10)
C110.0226 (15)0.0137 (13)0.0254 (15)0.0029 (11)0.0022 (12)0.0041 (11)
C120.0156 (13)0.0188 (14)0.0229 (14)0.0012 (11)0.0050 (11)0.0032 (11)
C130.0155 (13)0.0137 (13)0.0156 (13)0.0000 (11)0.0001 (10)0.0010 (10)
C140.0222 (15)0.0149 (13)0.0222 (14)0.0034 (11)0.0032 (12)0.0032 (11)
C150.0159 (13)0.0214 (14)0.0210 (14)0.0006 (11)0.0051 (11)0.0023 (11)
C160.0181 (14)0.0133 (13)0.0124 (12)0.0006 (11)0.0001 (10)0.0009 (10)
C170.043 (2)0.064 (3)0.040 (2)0.006 (2)0.0035 (18)0.017 (2)
C180.041 (2)0.054 (2)0.042 (2)0.0116 (18)0.0001 (17)0.0124 (18)
C190.059 (3)0.080 (3)0.029 (2)0.015 (2)0.0006 (19)0.009 (2)
C200.061 (3)0.147 (6)0.051 (3)0.001 (3)0.024 (2)0.048 (3)
C210.051 (2)0.048 (2)0.052 (2)0.013 (2)0.005 (2)0.0104 (19)
C220.055 (3)0.045 (2)0.040 (2)0.0051 (19)0.0066 (19)0.0160 (18)
C230.064 (3)0.061 (3)0.030 (2)0.019 (2)0.0014 (19)0.0039 (18)
C240.102 (4)0.097 (4)0.058 (3)0.009 (3)0.046 (3)0.029 (3)
Geometric parameters (Å, º) top
Zn1—O12.100 (2)C5—C61.510 (4)
Zn1—O32.032 (2)C6—C71.394 (4)
Zn1—O52.026 (2)C6—C8iv1.395 (4)
Zn1—O7i2.027 (2)C7—C81.386 (4)
Zn1—O1W1.954 (2)C7—H70.93
Zn1—Zn22.9527 (4)C8—C6iv1.395 (4)
Zn2—O22.058 (2)C8—H80.93
Zn2—O42.025 (2)C9—C101.501 (4)
Zn2—O62.018 (2)C10—C151.394 (4)
Zn2—O8i2.080 (2)C10—C111.395 (4)
Zn2—O2W1.969 (2)C11—C121.386 (4)
O1—C11.271 (3)C11—H110.93
O2—C11.241 (3)C12—C131.392 (4)
O3—C51.253 (3)C12—H120.93
O4—C51.258 (3)C13—C141.397 (4)
O5—C91.252 (4)C13—C161.503 (4)
O6—C91.262 (4)C14—C151.381 (4)
O7—C161.255 (3)C14—H140.93
O7—Zn1ii2.0274 (19)C15—H150.93
O8—C161.264 (3)C17—C181.543 (6)
O8—Zn2ii2.0804 (19)C18—H18A0.96
O9—C171.246 (5)C18—H18B0.96
O10—C221.252 (5)C18—H18C0.96
O1W—H1W10.842 (10)C19—H19A0.96
O1W—H1W20.842 (10)C19—H19B0.96
O2W—H2W10.849 (10)C19—H19C0.96
O2W—H2W20.841 (10)C20—H20A0.96
N1—C171.290 (5)C20—H20B0.96
N1—C191.479 (6)C20—H20C0.96
N1—C201.472 (6)C21—C221.544 (6)
N2—C221.292 (5)C21—H21A0.96
N2—C231.453 (6)C21—H21B0.96
N2—C241.477 (5)C21—H21C0.96
C1—C21.511 (4)C23—H23A0.96
C2—C31.394 (4)C23—H23B0.96
C2—C4iii1.399 (4)C23—H23C0.96
C3—C41.391 (4)C24—H24A0.96
C3—H30.93C24—H24B0.96
C4—C2iii1.399 (4)C24—H24C0.96
C4—H40.93
O1W—Zn1—O5102.58 (9)C6—C7—H7119.7
O1W—Zn1—O7i102.98 (9)C7—C8—C6iv119.8 (3)
O5—Zn1—O7i154.30 (9)C7—C8—H8120.1
O1W—Zn1—O398.14 (8)C6iv—C8—H8120.1
O5—Zn1—O387.61 (9)O5—C9—O6125.5 (3)
O7i—Zn1—O391.40 (8)O5—C9—C10116.7 (3)
O1W—Zn1—O1100.14 (8)O6—C9—C10117.8 (3)
O5—Zn1—O185.75 (9)C15—C10—C11119.5 (3)
O7i—Zn1—O187.20 (8)C15—C10—C9120.1 (3)
O3—Zn1—O1161.51 (8)C11—C10—C9120.3 (3)
O1W—Zn1—Zn2173.06 (6)C12—C11—C10119.6 (3)
O5—Zn1—Zn273.54 (6)C12—C11—H11120.2
O7i—Zn1—Zn281.29 (6)C10—C11—H11120.2
O3—Zn1—Zn276.13 (6)C11—C12—C13120.7 (3)
O1—Zn1—Zn285.44 (6)C11—C12—H12119.6
O2W—Zn2—O6102.78 (9)C13—C12—H12119.6
O2W—Zn2—O4107.47 (9)C12—C13—C14119.6 (2)
O6—Zn2—O488.71 (9)C12—C13—C16120.1 (2)
O2W—Zn2—O298.12 (8)C14—C13—C16120.3 (2)
O6—Zn2—O289.76 (9)C15—C14—C13119.6 (3)
O4—Zn2—O2154.05 (8)C15—C14—H14120.2
O2W—Zn2—O8i96.33 (8)C13—C14—H14120.2
O6—Zn2—O8i160.78 (9)C14—C15—C10120.9 (3)
O4—Zn2—O8i87.53 (8)C14—C15—H15119.6
O2—Zn2—O8i85.46 (8)C10—C15—H15119.6
O2W—Zn2—Zn1167.77 (6)O7—C16—O8124.9 (2)
O6—Zn2—Zn184.84 (7)O7—C16—C13117.7 (2)
O4—Zn2—Zn181.98 (6)O8—C16—C13117.5 (2)
O2—Zn2—Zn172.09 (6)O9—C17—N1121.2 (4)
O8i—Zn2—Zn175.97 (6)O9—C17—C18122.0 (4)
C1—O1—Zn1115.60 (17)N1—C17—C18116.7 (4)
C1—O2—Zn2135.28 (18)C17—C18—H18A109.5
C5—O3—Zn1128.33 (19)C17—C18—H18B109.5
C5—O4—Zn2122.57 (18)H18A—C18—H18B109.5
C9—O5—Zn1134.0 (2)C17—C18—H18C109.5
C9—O6—Zn2118.93 (19)H18A—C18—H18C109.5
C16—O7—Zn1ii123.68 (17)H18B—C18—H18C109.5
C16—O8—Zn2ii126.38 (17)N1—C19—H19A109.5
Zn1—O1W—H1W1123 (3)N1—C19—H19B109.5
Zn1—O1W—H1W2119 (3)H19A—C19—H19B109.5
H1W1—O1W—H1W2111 (4)N1—C19—H19C109.5
Zn2—O2W—H2W1114 (3)H19A—C19—H19C109.5
Zn2—O2W—H2W2120 (3)H19B—C19—H19C109.5
H2W1—O2W—H2W2107 (4)N1—C20—H20A109.5
C17—N1—C19117.3 (4)N1—C20—H20B109.5
C17—N1—C20124.4 (5)H20A—C20—H20B109.5
C19—N1—C20118.4 (4)N1—C20—H20C109.5
C22—N2—C23118.8 (4)H20A—C20—H20C109.5
C22—N2—C24123.3 (5)H20B—C20—H20C109.5
C23—N2—C24117.9 (4)C22—C21—H21A109.5
O2—C1—O1125.4 (3)C22—C21—H21B109.5
O2—C1—C2117.0 (2)H21A—C21—H21B109.5
O1—C1—C2117.6 (2)C22—C21—H21C109.5
C3—C2—C4iii119.6 (3)H21A—C21—H21C109.5
C3—C2—C1121.2 (2)H21B—C21—H21C109.5
C4iii—C2—C1119.3 (2)O10—C22—N2120.5 (4)
C4—C3—C2119.9 (3)O10—C22—C21121.4 (4)
C4—C3—H3120.0N2—C22—C21118.1 (4)
C2—C3—H3120.0N2—C23—H23A109.5
C3—C4—C2iii120.5 (3)N2—C23—H23B109.5
C3—C4—H4119.7H23A—C23—H23B109.5
C2iii—C4—H4119.7N2—C23—H23C109.5
O3—C5—O4125.8 (2)H23A—C23—H23C109.5
O3—C5—C6117.2 (2)H23B—C23—H23C109.5
O4—C5—C6117.0 (2)N2—C24—H24A109.5
C7—C6—C8iv119.7 (3)N2—C24—H24B109.5
C7—C6—C5119.6 (3)H24A—C24—H24B109.5
C8iv—C6—C5120.7 (3)N2—C24—H24C109.5
C8—C7—C6120.5 (3)H24A—C24—H24C109.5
C8—C7—H7119.7H24B—C24—H24C109.5
O1W—Zn1—O1—C1165.7 (2)O3—C5—C6—C713.9 (4)
O5—Zn1—O1—C192.2 (2)O4—C5—C6—C7165.0 (3)
O7i—Zn1—O1—C163.1 (2)O3—C5—C6—C8iv167.6 (3)
O3—Zn1—O1—C123.0 (4)O4—C5—C6—C8iv13.6 (4)
O2W—Zn2—O2—C1162.7 (3)C8iv—C6—C7—C80.3 (5)
O6—Zn2—O2—C159.8 (3)C5—C6—C7—C8178.3 (3)
O4—Zn2—O2—C126.7 (4)C6—C7—C8—C6iv0.3 (5)
O8i—Zn2—O2—C1101.5 (3)Zn1—O5—C9—O66.5 (5)
O1W—Zn1—O3—C5152.7 (2)Zn1—O5—C9—C10175.55 (19)
O5—Zn1—O3—C550.3 (2)Zn2—O6—C9—O512.3 (4)
O7i—Zn1—O3—C5104.0 (2)Zn2—O6—C9—C10165.71 (18)
O1—Zn1—O3—C518.7 (4)O5—C9—C10—C15160.6 (3)
Zn2—Zn1—O3—C523.3 (2)O6—C9—C10—C1517.5 (4)
O2W—Zn2—O4—C5159.7 (2)O5—C9—C10—C1116.2 (4)
O6—Zn2—O4—C597.3 (2)O6—C9—C10—C11165.7 (3)
O2—Zn2—O4—C510.5 (4)C15—C10—C11—C120.6 (4)
O8i—Zn2—O4—C563.8 (2)C9—C10—C11—C12177.4 (3)
Zn1—Zn2—O4—C512.3 (2)C10—C11—C12—C131.0 (4)
O1W—Zn1—O5—C9171.8 (3)C11—C12—C13—C140.7 (4)
O7i—Zn1—O5—C92.1 (4)C11—C12—C13—C16179.5 (2)
O3—Zn1—O5—C990.4 (3)C12—C13—C14—C150.1 (4)
O1—Zn1—O5—C972.4 (3)C16—C13—C14—C15178.7 (2)
O2W—Zn2—O6—C9173.9 (2)C13—C14—C15—C100.5 (4)
O4—Zn2—O6—C966.3 (2)C11—C10—C15—C140.2 (4)
O2—Zn2—O6—C987.8 (2)C9—C10—C15—C14176.7 (3)
O8i—Zn2—O6—C912.4 (4)Zn1ii—O7—C16—O86.6 (4)
Zn2—O2—C1—O118.1 (5)Zn1ii—O7—C16—C13173.87 (16)
Zn2—O2—C1—C2162.33 (19)Zn2ii—O8—C16—O722.5 (4)
Zn1—O1—C1—O29.3 (4)Zn2ii—O8—C16—C13157.04 (17)
Zn1—O1—C1—C2170.23 (18)C12—C13—C16—O79.4 (4)
O2—C1—C2—C3175.7 (3)C14—C13—C16—O7169.4 (2)
O1—C1—C2—C33.9 (4)C12—C13—C16—O8171.0 (2)
O2—C1—C2—C4iii3.9 (4)C14—C13—C16—O810.1 (4)
O1—C1—C2—C4iii176.5 (3)C19—N1—C17—O90.9 (6)
C4iii—C2—C3—C40.0 (5)C20—N1—C17—O9178.5 (4)
C1—C2—C3—C4179.6 (3)C19—N1—C17—C18178.7 (4)
C2—C3—C4—C2iii0.0 (5)C20—N1—C17—C181.8 (7)
Zn1—O3—C5—O423.0 (4)C23—N2—C22—O101.8 (6)
Zn1—O3—C5—C6155.74 (19)C24—N2—C22—O10179.5 (4)
Zn2—O4—C5—O30.0 (4)C23—N2—C22—C21178.4 (4)
Zn2—O4—C5—C6178.80 (18)C24—N2—C22—C210.3 (6)
Symmetry codes: (i) x+1, y1, z; (ii) x1, y+1, z; (iii) x+1, y+1, z+2; (iv) x+2, y+2, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1w—H1w1···O90.84 (1)1.76 (1)2.598 (3)173 (4)
O1w—H1w2···O8v0.84 (1)1.90 (1)2.734 (3)173 (4)
O2w—H2w1···O100.85 (1)1.76 (1)2.613 (3)177 (4)
O2w—H2w2···O1vi0.84 (1)2.03 (1)2.869 (3)176 (4)
Symmetry codes: (v) x, y1, z; (vi) x+1, y, z.

Experimental details

Crystal data
Chemical formula[Zn2(C8H4O4)2(H2O)2]·2C4H9NO
Mr669.24
Crystal system, space groupTriclinic, P1
Temperature (K)295
a, b, c (Å)6.9291 (5), 10.0551 (7), 20.620 (2)
α, β, γ (°)78.030 (1), 81.044 (1), 77.266 (1)
V3)1361.7 (2)
Z2
Radiation typeMo Kα
µ (mm1)1.83
Crystal size (mm)0.33 × 0.31 × 0.29
Data collection
DiffractometerBruker APEXII area-detector
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 1996)
Tmin, Tmax0.587, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
7748, 5269, 4503
Rint0.016
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.035, 0.099, 1.04
No. of reflections5269
No. of parameters383
No. of restraints4
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)1.24, 0.44

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2006), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), X-SEED (Barbour, 2001) and OLEX (Dolomanov et al., 2003), publCIF (Westrip, 2007).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1w—H1w1···O90.84 (1)1.76 (1)2.598 (3)173 (4)
O1w—H1w2···O8i0.84 (1)1.90 (1)2.734 (3)173 (4)
O2w—H2w1···O100.85 (1)1.76 (1)2.613 (3)177 (4)
O2w—H2w2···O1ii0.84 (1)2.03 (1)2.869 (3)176 (4)
Symmetry codes: (i) x, y1, z; (ii) x+1, y, z.
 

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