Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807060357/ci2501sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807060357/ci2501Isup2.hkl |
CCDC reference: 672741
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.
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.
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).
[Zn2(C8H4O4)2(H2O)2]·2C4H9NO | Z = 2 |
Mr = 669.24 | F(000) = 688 |
Triclinic, P1 | Dx = 1.632 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.9291 (5) Å | Cell parameters from 3838 reflections |
b = 10.0551 (7) Å | θ = 2.2–26.0° |
c = 20.620 (2) Å | µ = 1.83 mm−1 |
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 |
Bruker APEXII area-detector diffractometer | 5269 independent reflections |
Radiation source: fine-focus sealed tube | 4503 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.016 |
ϕ and ω scans | θmax = 26.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −8→6 |
Tmin = 0.587, Tmax = 1.000 | k = −12→12 |
7748 measured reflections | l = −25→25 |
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)] = 0.035 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.099 | H 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 parameters | Δρmax = 1.24 e Å−3 |
4 restraints | Δρmin = −0.44 e Å−3 |
[Zn2(C8H4O4)2(H2O)2]·2C4H9NO | γ = 77.266 (1)° |
Mr = 669.24 | V = 1361.7 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 6.9291 (5) Å | Mo Kα radiation |
b = 10.0551 (7) Å | µ = 1.83 mm−1 |
c = 20.620 (2) Å | T = 295 K |
α = 78.030 (1)° | 0.33 × 0.31 × 0.29 mm |
β = 81.044 (1)° |
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 = 1.000 | Rint = 0.016 |
7748 measured reflections |
R[F2 > 2σ(F2)] = 0.035 | 4 restraints |
wR(F2) = 0.099 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.04 | Δρmax = 1.24 e Å−3 |
5269 reflections | Δρmin = −0.44 e Å−3 |
383 parameters |
x | y | z | Uiso*/Ueq | ||
Zn1 | 0.63480 (4) | 0.67635 (3) | 0.719133 (14) | 0.01316 (10) | |
Zn2 | 0.92767 (4) | 0.77920 (3) | 0.775812 (14) | 0.01324 (10) | |
O1 | 0.5123 (3) | 0.6234 (2) | 0.81850 (9) | 0.0236 (5) | |
O2 | 0.7888 (3) | 0.6531 (2) | 0.85183 (9) | 0.0245 (5) | |
O3 | 0.8096 (3) | 0.7535 (2) | 0.63769 (9) | 0.0250 (5) | |
O4 | 0.9806 (3) | 0.8735 (2) | 0.67983 (9) | 0.0246 (5) | |
O5 | 0.5119 (3) | 0.8748 (2) | 0.72861 (11) | 0.0299 (5) | |
O6 | 0.7024 (3) | 0.9401 (2) | 0.78959 (11) | 0.0309 (5) | |
O7 | −0.1614 (3) | 1.49770 (19) | 0.73505 (10) | 0.0219 (4) | |
O8 | 0.0874 (3) | 1.59581 (19) | 0.74699 (10) | 0.0206 (4) | |
O9 | 0.4592 (4) | 0.6915 (3) | 0.54349 (11) | 0.0450 (7) | |
O10 | 1.0286 (4) | 0.8186 (3) | 0.95154 (12) | 0.0467 (7) | |
O1W | 0.4426 (3) | 0.6272 (2) | 0.67268 (10) | 0.0236 (5) | |
O2W | 1.1323 (3) | 0.8078 (2) | 0.82510 (10) | 0.0217 (4) | |
N1 | 0.3480 (6) | 0.7018 (5) | 0.44740 (18) | 0.0657 (11) | |
N2 | 1.1224 (6) | 0.8029 (4) | 1.05090 (18) | 0.0602 (10) | |
C1 | 0.6258 (4) | 0.6158 (3) | 0.86252 (13) | 0.0178 (6) | |
C2 | 0.5584 (4) | 0.5557 (3) | 0.93373 (13) | 0.0181 (6) | |
C3 | 0.3839 (4) | 0.5026 (3) | 0.94995 (14) | 0.0226 (6) | |
H3 | 0.3063 | 0.5042 | 0.9167 | 0.027* | |
C4 | 0.3260 (4) | 0.4472 (3) | 1.01590 (14) | 0.0231 (6) | |
H4 | 0.2096 | 0.4118 | 1.0266 | 0.028* | |
C5 | 0.9142 (4) | 0.8430 (3) | 0.63250 (13) | 0.0192 (6) | |
C6 | 0.9616 (4) | 0.9236 (3) | 0.56353 (13) | 0.0201 (6) | |
C7 | 0.8558 (5) | 0.9188 (3) | 0.51209 (14) | 0.0257 (7) | |
H7 | 0.7594 | 0.8641 | 0.5203 | 0.031* | |
C8 | 0.8933 (5) | 0.9948 (3) | 0.44886 (14) | 0.0256 (7) | |
H8 | 0.8218 | 0.9915 | 0.4148 | 0.031* | |
C9 | 0.5516 (4) | 0.9592 (3) | 0.75905 (13) | 0.0199 (6) | |
C10 | 0.4100 (4) | 1.0962 (3) | 0.75689 (13) | 0.0180 (6) | |
C11 | 0.2208 (4) | 1.1129 (3) | 0.73742 (14) | 0.0206 (6) | |
H11 | 0.1796 | 1.0382 | 0.7274 | 0.025* | |
C12 | 0.0946 (4) | 1.2414 (3) | 0.73307 (14) | 0.0192 (6) | |
H12 | −0.0323 | 1.2522 | 0.7208 | 0.023* | |
C13 | 0.1558 (4) | 1.3544 (3) | 0.74688 (13) | 0.0158 (5) | |
C14 | 0.3456 (4) | 1.3378 (3) | 0.76604 (14) | 0.0198 (6) | |
H14 | 0.3878 | 1.4128 | 0.7753 | 0.024* | |
C15 | 0.4704 (4) | 1.2094 (3) | 0.77112 (14) | 0.0200 (6) | |
H15 | 0.5963 | 1.1982 | 0.7842 | 0.024* | |
C16 | 0.0166 (4) | 1.4929 (3) | 0.74250 (12) | 0.0157 (5) | |
C17 | 0.3473 (6) | 0.6572 (5) | 0.5108 (2) | 0.0507 (10) | |
C18 | 0.2010 (6) | 0.5604 (4) | 0.54366 (19) | 0.0452 (9) | |
H18A | 0.2192 | 0.5293 | 0.5900 | 0.068* | |
H18B | 0.2261 | 0.4819 | 0.5217 | 0.068* | |
H18C | 0.0668 | 0.6099 | 0.5398 | 0.068* | |
C19 | 0.4846 (7) | 0.7971 (5) | 0.41555 (19) | 0.0590 (12) | |
H19A | 0.5368 | 0.8269 | 0.4494 | 0.088* | |
H19B | 0.4133 | 0.8762 | 0.3883 | 0.088* | |
H19C | 0.5923 | 0.7499 | 0.3883 | 0.088* | |
C20 | 0.2240 (8) | 0.6634 (7) | 0.4052 (2) | 0.0832 (19) | |
H20A | 0.1502 | 0.5966 | 0.4315 | 0.125* | |
H20B | 0.3077 | 0.6242 | 0.3694 | 0.125* | |
H20C | 0.1330 | 0.7444 | 0.3870 | 0.125* | |
C21 | 1.3211 (6) | 0.9137 (4) | 0.9555 (2) | 0.0496 (10) | |
H21A | 1.3178 | 0.9395 | 0.9081 | 0.074* | |
H21B | 1.4445 | 0.8517 | 0.9646 | 0.074* | |
H21C | 1.3099 | 0.9952 | 0.9743 | 0.074* | |
C22 | 1.1458 (6) | 0.8407 (4) | 0.9868 (2) | 0.0478 (10) | |
C23 | 0.9614 (7) | 0.7308 (5) | 1.08110 (19) | 0.0524 (11) | |
H23A | 0.8818 | 0.7282 | 1.0474 | 0.079* | |
H23B | 0.8800 | 0.7787 | 1.1145 | 0.079* | |
H23C | 1.0160 | 0.6379 | 1.1014 | 0.079* | |
C24 | 1.2542 (9) | 0.8267 (6) | 1.0954 (2) | 0.0812 (17) | |
H24A | 1.3640 | 0.8633 | 1.0690 | 0.122* | |
H24B | 1.3037 | 0.7406 | 1.1233 | 0.122* | |
H24C | 1.1806 | 0.8916 | 1.1228 | 0.122* | |
H1W1 | 0.438 (6) | 0.652 (4) | 0.6313 (6) | 0.041 (11)* | |
H1W2 | 0.329 (3) | 0.620 (4) | 0.6927 (18) | 0.060 (14)* | |
H2W1 | 1.095 (6) | 0.811 (4) | 0.8661 (7) | 0.048 (12)* | |
H2W2 | 1.246 (3) | 0.757 (3) | 0.8228 (19) | 0.050 (12)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.01266 (17) | 0.01296 (17) | 0.01259 (16) | −0.00214 (12) | −0.00050 (12) | −0.00054 (12) |
Zn2 | 0.01314 (17) | 0.01313 (17) | 0.01196 (16) | −0.00188 (12) | −0.00091 (12) | −0.00006 (12) |
O1 | 0.0223 (11) | 0.0349 (12) | 0.0117 (9) | −0.0074 (9) | −0.0020 (8) | 0.0016 (8) |
O2 | 0.0229 (11) | 0.0334 (12) | 0.0158 (10) | −0.0130 (9) | 0.0005 (8) | 0.0049 (8) |
O3 | 0.0275 (11) | 0.0304 (12) | 0.0159 (10) | −0.0136 (9) | 0.0000 (8) | 0.0049 (8) |
O4 | 0.0368 (12) | 0.0277 (11) | 0.0107 (9) | −0.0144 (10) | −0.0016 (9) | 0.0015 (8) |
O5 | 0.0283 (12) | 0.0173 (11) | 0.0415 (13) | 0.0057 (9) | −0.0045 (10) | −0.0099 (9) |
O6 | 0.0290 (12) | 0.0245 (11) | 0.0347 (12) | 0.0101 (9) | −0.0097 (10) | −0.0070 (9) |
O7 | 0.0157 (10) | 0.0156 (10) | 0.0333 (11) | 0.0009 (8) | −0.0069 (9) | −0.0032 (8) |
O8 | 0.0164 (10) | 0.0132 (9) | 0.0313 (11) | −0.0012 (8) | −0.0006 (8) | −0.0051 (8) |
O9 | 0.0446 (15) | 0.0735 (19) | 0.0225 (12) | −0.0206 (14) | −0.0096 (11) | −0.0071 (12) |
O10 | 0.0457 (16) | 0.073 (2) | 0.0252 (12) | −0.0122 (14) | −0.0069 (11) | −0.0158 (12) |
O1W | 0.0185 (11) | 0.0388 (13) | 0.0160 (10) | −0.0122 (9) | −0.0023 (9) | −0.0029 (9) |
O2W | 0.0167 (10) | 0.0306 (12) | 0.0183 (10) | −0.0030 (9) | −0.0021 (8) | −0.0073 (9) |
N1 | 0.050 (2) | 0.104 (3) | 0.043 (2) | −0.001 (2) | −0.0125 (17) | −0.023 (2) |
N2 | 0.071 (3) | 0.069 (3) | 0.044 (2) | −0.006 (2) | −0.0204 (19) | −0.0154 (18) |
C1 | 0.0162 (13) | 0.0167 (13) | 0.0164 (13) | 0.0005 (11) | 0.0011 (11) | −0.0003 (11) |
C2 | 0.0203 (14) | 0.0187 (14) | 0.0131 (12) | −0.0052 (11) | 0.0017 (11) | 0.0009 (11) |
C3 | 0.0226 (15) | 0.0318 (16) | 0.0141 (13) | −0.0106 (13) | −0.0022 (11) | 0.0002 (12) |
C4 | 0.0196 (14) | 0.0309 (16) | 0.0185 (14) | −0.0119 (12) | −0.0002 (11) | 0.0018 (12) |
C5 | 0.0206 (14) | 0.0174 (14) | 0.0148 (13) | −0.0017 (11) | 0.0016 (11) | 0.0026 (11) |
C6 | 0.0244 (15) | 0.0210 (14) | 0.0131 (13) | −0.0075 (12) | 0.0018 (11) | 0.0014 (11) |
C7 | 0.0300 (16) | 0.0296 (16) | 0.0185 (14) | −0.0156 (13) | −0.0019 (12) | 0.0034 (12) |
C8 | 0.0318 (17) | 0.0323 (17) | 0.0150 (14) | −0.0162 (14) | −0.0038 (12) | 0.0022 (12) |
C9 | 0.0213 (15) | 0.0141 (13) | 0.0178 (13) | 0.0016 (11) | 0.0030 (11) | 0.0025 (11) |
C10 | 0.0208 (14) | 0.0150 (13) | 0.0154 (13) | 0.0010 (11) | 0.0002 (11) | −0.0026 (10) |
C11 | 0.0226 (15) | 0.0137 (13) | 0.0254 (15) | −0.0029 (11) | −0.0022 (12) | −0.0041 (11) |
C12 | 0.0156 (13) | 0.0188 (14) | 0.0229 (14) | −0.0012 (11) | −0.0050 (11) | −0.0032 (11) |
C13 | 0.0155 (13) | 0.0137 (13) | 0.0156 (13) | 0.0000 (11) | 0.0001 (10) | −0.0010 (10) |
C14 | 0.0222 (15) | 0.0149 (13) | 0.0222 (14) | −0.0034 (11) | −0.0032 (12) | −0.0032 (11) |
C15 | 0.0159 (13) | 0.0214 (14) | 0.0210 (14) | 0.0006 (11) | −0.0051 (11) | −0.0023 (11) |
C16 | 0.0181 (14) | 0.0133 (13) | 0.0124 (12) | −0.0006 (11) | −0.0001 (10) | 0.0009 (10) |
C17 | 0.043 (2) | 0.064 (3) | 0.040 (2) | 0.006 (2) | −0.0035 (18) | −0.017 (2) |
C18 | 0.041 (2) | 0.054 (2) | 0.042 (2) | −0.0116 (18) | 0.0001 (17) | −0.0124 (18) |
C19 | 0.059 (3) | 0.080 (3) | 0.029 (2) | −0.015 (2) | −0.0006 (19) | 0.009 (2) |
C20 | 0.061 (3) | 0.147 (6) | 0.051 (3) | 0.001 (3) | −0.024 (2) | −0.048 (3) |
C21 | 0.051 (2) | 0.048 (2) | 0.052 (2) | −0.013 (2) | −0.005 (2) | −0.0104 (19) |
C22 | 0.055 (3) | 0.045 (2) | 0.040 (2) | 0.0051 (19) | −0.0066 (19) | −0.0160 (18) |
C23 | 0.064 (3) | 0.061 (3) | 0.030 (2) | −0.019 (2) | 0.0014 (19) | −0.0039 (18) |
C24 | 0.102 (4) | 0.097 (4) | 0.058 (3) | −0.009 (3) | −0.046 (3) | −0.029 (3) |
Zn1—O1 | 2.100 (2) | C5—C6 | 1.510 (4) |
Zn1—O3 | 2.032 (2) | C6—C7 | 1.394 (4) |
Zn1—O5 | 2.026 (2) | C6—C8iv | 1.395 (4) |
Zn1—O7i | 2.027 (2) | C7—C8 | 1.386 (4) |
Zn1—O1W | 1.954 (2) | C7—H7 | 0.93 |
Zn1—Zn2 | 2.9527 (4) | C8—C6iv | 1.395 (4) |
Zn2—O2 | 2.058 (2) | C8—H8 | 0.93 |
Zn2—O4 | 2.025 (2) | C9—C10 | 1.501 (4) |
Zn2—O6 | 2.018 (2) | C10—C15 | 1.394 (4) |
Zn2—O8i | 2.080 (2) | C10—C11 | 1.395 (4) |
Zn2—O2W | 1.969 (2) | C11—C12 | 1.386 (4) |
O1—C1 | 1.271 (3) | C11—H11 | 0.93 |
O2—C1 | 1.241 (3) | C12—C13 | 1.392 (4) |
O3—C5 | 1.253 (3) | C12—H12 | 0.93 |
O4—C5 | 1.258 (3) | C13—C14 | 1.397 (4) |
O5—C9 | 1.252 (4) | C13—C16 | 1.503 (4) |
O6—C9 | 1.262 (4) | C14—C15 | 1.381 (4) |
O7—C16 | 1.255 (3) | C14—H14 | 0.93 |
O7—Zn1ii | 2.0274 (19) | C15—H15 | 0.93 |
O8—C16 | 1.264 (3) | C17—C18 | 1.543 (6) |
O8—Zn2ii | 2.0804 (19) | C18—H18A | 0.96 |
O9—C17 | 1.246 (5) | C18—H18B | 0.96 |
O10—C22 | 1.252 (5) | C18—H18C | 0.96 |
O1W—H1W1 | 0.842 (10) | C19—H19A | 0.96 |
O1W—H1W2 | 0.842 (10) | C19—H19B | 0.96 |
O2W—H2W1 | 0.849 (10) | C19—H19C | 0.96 |
O2W—H2W2 | 0.841 (10) | C20—H20A | 0.96 |
N1—C17 | 1.290 (5) | C20—H20B | 0.96 |
N1—C19 | 1.479 (6) | C20—H20C | 0.96 |
N1—C20 | 1.472 (6) | C21—C22 | 1.544 (6) |
N2—C22 | 1.292 (5) | C21—H21A | 0.96 |
N2—C23 | 1.453 (6) | C21—H21B | 0.96 |
N2—C24 | 1.477 (5) | C21—H21C | 0.96 |
C1—C2 | 1.511 (4) | C23—H23A | 0.96 |
C2—C3 | 1.394 (4) | C23—H23B | 0.96 |
C2—C4iii | 1.399 (4) | C23—H23C | 0.96 |
C3—C4 | 1.391 (4) | C24—H24A | 0.96 |
C3—H3 | 0.93 | C24—H24B | 0.96 |
C4—C2iii | 1.399 (4) | C24—H24C | 0.96 |
C4—H4 | 0.93 | ||
O1W—Zn1—O5 | 102.58 (9) | C6—C7—H7 | 119.7 |
O1W—Zn1—O7i | 102.98 (9) | C7—C8—C6iv | 119.8 (3) |
O5—Zn1—O7i | 154.30 (9) | C7—C8—H8 | 120.1 |
O1W—Zn1—O3 | 98.14 (8) | C6iv—C8—H8 | 120.1 |
O5—Zn1—O3 | 87.61 (9) | O5—C9—O6 | 125.5 (3) |
O7i—Zn1—O3 | 91.40 (8) | O5—C9—C10 | 116.7 (3) |
O1W—Zn1—O1 | 100.14 (8) | O6—C9—C10 | 117.8 (3) |
O5—Zn1—O1 | 85.75 (9) | C15—C10—C11 | 119.5 (3) |
O7i—Zn1—O1 | 87.20 (8) | C15—C10—C9 | 120.1 (3) |
O3—Zn1—O1 | 161.51 (8) | C11—C10—C9 | 120.3 (3) |
O1W—Zn1—Zn2 | 173.06 (6) | C12—C11—C10 | 119.6 (3) |
O5—Zn1—Zn2 | 73.54 (6) | C12—C11—H11 | 120.2 |
O7i—Zn1—Zn2 | 81.29 (6) | C10—C11—H11 | 120.2 |
O3—Zn1—Zn2 | 76.13 (6) | C11—C12—C13 | 120.7 (3) |
O1—Zn1—Zn2 | 85.44 (6) | C11—C12—H12 | 119.6 |
O2W—Zn2—O6 | 102.78 (9) | C13—C12—H12 | 119.6 |
O2W—Zn2—O4 | 107.47 (9) | C12—C13—C14 | 119.6 (2) |
O6—Zn2—O4 | 88.71 (9) | C12—C13—C16 | 120.1 (2) |
O2W—Zn2—O2 | 98.12 (8) | C14—C13—C16 | 120.3 (2) |
O6—Zn2—O2 | 89.76 (9) | C15—C14—C13 | 119.6 (3) |
O4—Zn2—O2 | 154.05 (8) | C15—C14—H14 | 120.2 |
O2W—Zn2—O8i | 96.33 (8) | C13—C14—H14 | 120.2 |
O6—Zn2—O8i | 160.78 (9) | C14—C15—C10 | 120.9 (3) |
O4—Zn2—O8i | 87.53 (8) | C14—C15—H15 | 119.6 |
O2—Zn2—O8i | 85.46 (8) | C10—C15—H15 | 119.6 |
O2W—Zn2—Zn1 | 167.77 (6) | O7—C16—O8 | 124.9 (2) |
O6—Zn2—Zn1 | 84.84 (7) | O7—C16—C13 | 117.7 (2) |
O4—Zn2—Zn1 | 81.98 (6) | O8—C16—C13 | 117.5 (2) |
O2—Zn2—Zn1 | 72.09 (6) | O9—C17—N1 | 121.2 (4) |
O8i—Zn2—Zn1 | 75.97 (6) | O9—C17—C18 | 122.0 (4) |
C1—O1—Zn1 | 115.60 (17) | N1—C17—C18 | 116.7 (4) |
C1—O2—Zn2 | 135.28 (18) | C17—C18—H18A | 109.5 |
C5—O3—Zn1 | 128.33 (19) | C17—C18—H18B | 109.5 |
C5—O4—Zn2 | 122.57 (18) | H18A—C18—H18B | 109.5 |
C9—O5—Zn1 | 134.0 (2) | C17—C18—H18C | 109.5 |
C9—O6—Zn2 | 118.93 (19) | H18A—C18—H18C | 109.5 |
C16—O7—Zn1ii | 123.68 (17) | H18B—C18—H18C | 109.5 |
C16—O8—Zn2ii | 126.38 (17) | N1—C19—H19A | 109.5 |
Zn1—O1W—H1W1 | 123 (3) | N1—C19—H19B | 109.5 |
Zn1—O1W—H1W2 | 119 (3) | H19A—C19—H19B | 109.5 |
H1W1—O1W—H1W2 | 111 (4) | N1—C19—H19C | 109.5 |
Zn2—O2W—H2W1 | 114 (3) | H19A—C19—H19C | 109.5 |
Zn2—O2W—H2W2 | 120 (3) | H19B—C19—H19C | 109.5 |
H2W1—O2W—H2W2 | 107 (4) | N1—C20—H20A | 109.5 |
C17—N1—C19 | 117.3 (4) | N1—C20—H20B | 109.5 |
C17—N1—C20 | 124.4 (5) | H20A—C20—H20B | 109.5 |
C19—N1—C20 | 118.4 (4) | N1—C20—H20C | 109.5 |
C22—N2—C23 | 118.8 (4) | H20A—C20—H20C | 109.5 |
C22—N2—C24 | 123.3 (5) | H20B—C20—H20C | 109.5 |
C23—N2—C24 | 117.9 (4) | C22—C21—H21A | 109.5 |
O2—C1—O1 | 125.4 (3) | C22—C21—H21B | 109.5 |
O2—C1—C2 | 117.0 (2) | H21A—C21—H21B | 109.5 |
O1—C1—C2 | 117.6 (2) | C22—C21—H21C | 109.5 |
C3—C2—C4iii | 119.6 (3) | H21A—C21—H21C | 109.5 |
C3—C2—C1 | 121.2 (2) | H21B—C21—H21C | 109.5 |
C4iii—C2—C1 | 119.3 (2) | O10—C22—N2 | 120.5 (4) |
C4—C3—C2 | 119.9 (3) | O10—C22—C21 | 121.4 (4) |
C4—C3—H3 | 120.0 | N2—C22—C21 | 118.1 (4) |
C2—C3—H3 | 120.0 | N2—C23—H23A | 109.5 |
C3—C4—C2iii | 120.5 (3) | N2—C23—H23B | 109.5 |
C3—C4—H4 | 119.7 | H23A—C23—H23B | 109.5 |
C2iii—C4—H4 | 119.7 | N2—C23—H23C | 109.5 |
O3—C5—O4 | 125.8 (2) | H23A—C23—H23C | 109.5 |
O3—C5—C6 | 117.2 (2) | H23B—C23—H23C | 109.5 |
O4—C5—C6 | 117.0 (2) | N2—C24—H24A | 109.5 |
C7—C6—C8iv | 119.7 (3) | N2—C24—H24B | 109.5 |
C7—C6—C5 | 119.6 (3) | H24A—C24—H24B | 109.5 |
C8iv—C6—C5 | 120.7 (3) | N2—C24—H24C | 109.5 |
C8—C7—C6 | 120.5 (3) | H24A—C24—H24C | 109.5 |
C8—C7—H7 | 119.7 | H24B—C24—H24C | 109.5 |
O1W—Zn1—O1—C1 | 165.7 (2) | O3—C5—C6—C7 | 13.9 (4) |
O5—Zn1—O1—C1 | −92.2 (2) | O4—C5—C6—C7 | −165.0 (3) |
O7i—Zn1—O1—C1 | 63.1 (2) | O3—C5—C6—C8iv | −167.6 (3) |
O3—Zn1—O1—C1 | −23.0 (4) | O4—C5—C6—C8iv | 13.6 (4) |
O2W—Zn2—O2—C1 | 162.7 (3) | C8iv—C6—C7—C8 | −0.3 (5) |
O6—Zn2—O2—C1 | 59.8 (3) | C5—C6—C7—C8 | 178.3 (3) |
O4—Zn2—O2—C1 | −26.7 (4) | C6—C7—C8—C6iv | 0.3 (5) |
O8i—Zn2—O2—C1 | −101.5 (3) | Zn1—O5—C9—O6 | 6.5 (5) |
O1W—Zn1—O3—C5 | 152.7 (2) | Zn1—O5—C9—C10 | −175.55 (19) |
O5—Zn1—O3—C5 | 50.3 (2) | Zn2—O6—C9—O5 | 12.3 (4) |
O7i—Zn1—O3—C5 | −104.0 (2) | Zn2—O6—C9—C10 | −165.71 (18) |
O1—Zn1—O3—C5 | −18.7 (4) | O5—C9—C10—C15 | −160.6 (3) |
Zn2—Zn1—O3—C5 | −23.3 (2) | O6—C9—C10—C15 | 17.5 (4) |
O2W—Zn2—O4—C5 | 159.7 (2) | O5—C9—C10—C11 | 16.2 (4) |
O6—Zn2—O4—C5 | −97.3 (2) | O6—C9—C10—C11 | −165.7 (3) |
O2—Zn2—O4—C5 | −10.5 (4) | C15—C10—C11—C12 | −0.6 (4) |
O8i—Zn2—O4—C5 | 63.8 (2) | C9—C10—C11—C12 | −177.4 (3) |
Zn1—Zn2—O4—C5 | −12.3 (2) | C10—C11—C12—C13 | 1.0 (4) |
O1W—Zn1—O5—C9 | 171.8 (3) | C11—C12—C13—C14 | −0.7 (4) |
O7i—Zn1—O5—C9 | −2.1 (4) | C11—C12—C13—C16 | −179.5 (2) |
O3—Zn1—O5—C9 | −90.4 (3) | C12—C13—C14—C15 | −0.1 (4) |
O1—Zn1—O5—C9 | 72.4 (3) | C16—C13—C14—C15 | 178.7 (2) |
O2W—Zn2—O6—C9 | 173.9 (2) | C13—C14—C15—C10 | 0.5 (4) |
O4—Zn2—O6—C9 | 66.3 (2) | C11—C10—C15—C14 | −0.2 (4) |
O2—Zn2—O6—C9 | −87.8 (2) | C9—C10—C15—C14 | 176.7 (3) |
O8i—Zn2—O6—C9 | −12.4 (4) | Zn1ii—O7—C16—O8 | 6.6 (4) |
Zn2—O2—C1—O1 | 18.1 (5) | Zn1ii—O7—C16—C13 | −173.87 (16) |
Zn2—O2—C1—C2 | −162.33 (19) | Zn2ii—O8—C16—O7 | 22.5 (4) |
Zn1—O1—C1—O2 | 9.3 (4) | Zn2ii—O8—C16—C13 | −157.04 (17) |
Zn1—O1—C1—C2 | −170.23 (18) | C12—C13—C16—O7 | 9.4 (4) |
O2—C1—C2—C3 | −175.7 (3) | C14—C13—C16—O7 | −169.4 (2) |
O1—C1—C2—C3 | 3.9 (4) | C12—C13—C16—O8 | −171.0 (2) |
O2—C1—C2—C4iii | 3.9 (4) | C14—C13—C16—O8 | 10.1 (4) |
O1—C1—C2—C4iii | −176.5 (3) | C19—N1—C17—O9 | −0.9 (6) |
C4iii—C2—C3—C4 | 0.0 (5) | C20—N1—C17—O9 | 178.5 (4) |
C1—C2—C3—C4 | 179.6 (3) | C19—N1—C17—C18 | 178.7 (4) |
C2—C3—C4—C2iii | 0.0 (5) | C20—N1—C17—C18 | −1.8 (7) |
Zn1—O3—C5—O4 | 23.0 (4) | C23—N2—C22—O10 | 1.8 (6) |
Zn1—O3—C5—C6 | −155.74 (19) | C24—N2—C22—O10 | −179.5 (4) |
Zn2—O4—C5—O3 | 0.0 (4) | C23—N2—C22—C21 | −178.4 (4) |
Zn2—O4—C5—C6 | 178.80 (18) | C24—N2—C22—C21 | 0.3 (6) |
Symmetry codes: (i) x+1, y−1, z; (ii) x−1, y+1, z; (iii) −x+1, −y+1, −z+2; (iv) −x+2, −y+2, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1w—H1w1···O9 | 0.84 (1) | 1.76 (1) | 2.598 (3) | 173 (4) |
O1w—H1w2···O8v | 0.84 (1) | 1.90 (1) | 2.734 (3) | 173 (4) |
O2w—H2w1···O10 | 0.85 (1) | 1.76 (1) | 2.613 (3) | 177 (4) |
O2w—H2w2···O1vi | 0.84 (1) | 2.03 (1) | 2.869 (3) | 176 (4) |
Symmetry codes: (v) x, y−1, z; (vi) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | [Zn2(C8H4O4)2(H2O)2]·2C4H9NO |
Mr | 669.24 |
Crystal system, space group | Triclinic, 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) |
V (Å3) | 1361.7 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.83 |
Crystal size (mm) | 0.33 × 0.31 × 0.29 |
Data collection | |
Diffractometer | Bruker APEXII area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.587, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7748, 5269, 4503 |
Rint | 0.016 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.035, 0.099, 1.04 |
No. of reflections | 5269 |
No. of parameters | 383 |
No. of restraints | 4 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 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).
D—H···A | D—H | H···A | D···A | D—H···A |
O1w—H1w1···O9 | 0.84 (1) | 1.76 (1) | 2.598 (3) | 173 (4) |
O1w—H1w2···O8i | 0.84 (1) | 1.90 (1) | 2.734 (3) | 173 (4) |
O2w—H2w1···O10 | 0.85 (1) | 1.76 (1) | 2.613 (3) | 177 (4) |
O2w—H2w2···O1ii | 0.84 (1) | 2.03 (1) | 2.869 (3) | 176 (4) |
Symmetry codes: (i) x, y−1, z; (ii) x+1, y, z. |
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.