Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805030734/sg6032sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805030734/sg6032Isup2.hkl |
CCDC reference: 287727
Key indicators
- Single-crystal X-ray study
- T = 283 K
- Mean (C-C) = 0.004 Å
- R factor = 0.037
- wR factor = 0.086
- Data-to-parameter ratio = 14.3
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings Differ .... ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............ 2.00 Ratio PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ?
Alert level G
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion
Compound (I) was prepared by hydrothermal methods. A mixture of Zn(NO3)2·6H2O (0.5 mmol), H4BTC (0.6 mmol), benzotriazole (1.0 mmol) and water (12 ml) was stirred for 20 min in air. The mixture was then transferred to a 23 ml Teflon reactor and kept at 433 K for 72 h under autogenous pressure. Colorless single crystals of (I) suitable for X-ray analysis were obtained from the reaction mixture.
H atoms were placed in calculated positions, with C—H = 0.93 Å and N—H = 0.86 Å, and treated as riding atoms in the final cycles of refinement, with Uiso(H) = 1.2Ueq(carrier).
Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (Bruker, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.
[Zn2(C10H2O8)(C6H5N3)4] | F(000) = 868 |
Mr = 857.38 | Dx = 1.797 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 15373 reflections |
a = 7.7961 (16) Å | θ = 3.1–27.5° |
b = 19.346 (4) Å | µ = 1.59 mm−1 |
c = 10.732 (2) Å | T = 283 K |
β = 101.78 (3)° | Block, colorless |
V = 1584.6 (6) Å3 | 0.26 × 0.22 × 0.17 mm |
Z = 2 |
Bruker SMART CCD area-detector diffractometer | 3628 independent reflections |
Radiation source: fine-focus sealed tube | 2924 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.049 |
Detector resolution: 0.01 pixels mm-1 | θmax = 27.5°, θmin = 3.1° |
ϕ and ω scans | h = −10→8 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996; Blessing, 1995) | k = −25→25 |
Tmin = 0.668, Tmax = 0.764 | l = −13→13 |
15373 measured reflections |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.086 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0405P)2 + 0.7439P] where P = (Fo2 + 2Fc2)/3 |
3628 reflections | (Δ/σ)max = 0.001 |
253 parameters | Δρmax = 0.43 e Å−3 |
0 restraints | Δρmin = −0.40 e Å−3 |
[Zn2(C10H2O8)(C6H5N3)4] | V = 1584.6 (6) Å3 |
Mr = 857.38 | Z = 2 |
Monoclinic, P21/n | Mo Kα radiation |
a = 7.7961 (16) Å | µ = 1.59 mm−1 |
b = 19.346 (4) Å | T = 283 K |
c = 10.732 (2) Å | 0.26 × 0.22 × 0.17 mm |
β = 101.78 (3)° |
Bruker SMART CCD area-detector diffractometer | 3628 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996; Blessing, 1995) | 2924 reflections with I > 2σ(I) |
Tmin = 0.668, Tmax = 0.764 | Rint = 0.049 |
15373 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.086 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.43 e Å−3 |
3628 reflections | Δρmin = −0.40 e Å−3 |
253 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. R-factors basedon 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 | 0.55321 (3) | 0.171003 (14) | 0.69136 (3) | 0.02101 (10) | |
C1 | 0.6901 (3) | 0.15219 (12) | 0.9807 (2) | 0.0228 (5) | |
C2 | 0.7874 (4) | 0.09133 (14) | 0.9873 (3) | 0.0333 (6) | |
H2A | 0.7980 | 0.0668 | 0.9147 | 0.040* | |
C3 | 0.8664 (4) | 0.06966 (16) | 1.1067 (3) | 0.0421 (8) | |
H3A | 0.9315 | 0.0290 | 1.1150 | 0.051* | |
C4 | 0.8528 (4) | 0.10642 (17) | 1.2169 (3) | 0.0415 (7) | |
H4A | 0.9110 | 0.0898 | 1.2956 | 0.050* | |
C5 | 0.7573 (4) | 0.16556 (16) | 1.2124 (3) | 0.0367 (7) | |
H5A | 0.7470 | 0.1897 | 1.2855 | 0.044* | |
C6 | 0.6758 (3) | 0.18757 (13) | 1.0907 (2) | 0.0261 (5) | |
C7 | 0.7177 (3) | 0.31540 (13) | 0.6532 (2) | 0.0232 (5) | |
C8 | 0.7323 (3) | 0.35627 (13) | 0.5496 (2) | 0.0252 (5) | |
C9 | 0.8252 (4) | 0.41858 (14) | 0.5624 (3) | 0.0332 (6) | |
H9A | 0.8359 | 0.4453 | 0.4923 | 0.040* | |
C10 | 0.8993 (4) | 0.43799 (15) | 0.6840 (3) | 0.0358 (6) | |
H10A | 0.9611 | 0.4794 | 0.6973 | 0.043* | |
C11 | 0.8844 (4) | 0.39678 (15) | 0.7896 (3) | 0.0355 (6) | |
H11A | 0.9369 | 0.4119 | 0.8707 | 0.043* | |
C12 | 0.7956 (3) | 0.33538 (14) | 0.7771 (3) | 0.0285 (6) | |
H12A | 0.7875 | 0.3083 | 0.8473 | 0.034* | |
C13 | 0.1163 (3) | 0.04787 (12) | 0.5713 (2) | 0.0183 (5) | |
C14 | 0.1753 (3) | −0.00192 (12) | 0.4983 (2) | 0.0205 (5) | |
H14A | 0.2939 | −0.0032 | 0.4963 | 0.025* | |
C15 | 0.0636 (3) | −0.05046 (12) | 0.4271 (2) | 0.0188 (5) | |
C16 | 0.2529 (3) | 0.09310 (12) | 0.6542 (2) | 0.0207 (5) | |
C17 | 0.1404 (3) | −0.10511 (12) | 0.3564 (2) | 0.0206 (5) | |
N1 | 0.5948 (3) | 0.18824 (11) | 0.8794 (2) | 0.0241 (4) | |
N2 | 0.5242 (3) | 0.24233 (11) | 0.9224 (2) | 0.0281 (5) | |
N3 | 0.5714 (3) | 0.24229 (11) | 1.0477 (2) | 0.0281 (5) | |
H3B | 0.5400 | 0.2732 | 1.0961 | 0.034* | |
N4 | 0.6183 (3) | 0.25884 (11) | 0.6069 (2) | 0.0248 (4) | |
N5 | 0.5729 (3) | 0.26344 (12) | 0.4822 (2) | 0.0310 (5) | |
N6 | 0.6404 (3) | 0.32113 (11) | 0.4472 (2) | 0.0304 (5) | |
H6A | 0.6280 | 0.3348 | 0.3697 | 0.037* | |
O1 | 0.3295 (2) | 0.13703 (10) | 0.59607 (17) | 0.0284 (4) | |
O2 | 0.2901 (3) | 0.08211 (12) | 0.76823 (19) | 0.0499 (6) | |
O3 | 0.0518 (2) | −0.15673 (9) | 0.31397 (18) | 0.0276 (4) | |
O4 | 0.2980 (2) | −0.09541 (9) | 0.3456 (2) | 0.0327 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.01939 (14) | 0.02260 (15) | 0.02110 (15) | −0.00202 (11) | 0.00430 (10) | −0.00557 (11) |
C1 | 0.0233 (11) | 0.0222 (12) | 0.0230 (13) | −0.0044 (10) | 0.0050 (10) | −0.0012 (9) |
C2 | 0.0350 (14) | 0.0279 (14) | 0.0384 (16) | −0.0006 (12) | 0.0105 (12) | −0.0024 (12) |
C3 | 0.0341 (15) | 0.0355 (16) | 0.054 (2) | 0.0041 (13) | 0.0038 (14) | 0.0149 (14) |
C4 | 0.0369 (15) | 0.0481 (18) | 0.0353 (17) | −0.0087 (14) | −0.0023 (13) | 0.0141 (14) |
C5 | 0.0372 (15) | 0.0467 (17) | 0.0244 (14) | −0.0142 (14) | 0.0019 (11) | −0.0025 (12) |
C6 | 0.0262 (12) | 0.0261 (13) | 0.0258 (13) | −0.0074 (10) | 0.0048 (10) | −0.0027 (10) |
C7 | 0.0217 (11) | 0.0236 (12) | 0.0248 (13) | 0.0023 (10) | 0.0058 (9) | 0.0009 (10) |
C8 | 0.0290 (12) | 0.0247 (12) | 0.0225 (13) | 0.0076 (11) | 0.0064 (10) | 0.0003 (10) |
C9 | 0.0401 (15) | 0.0262 (13) | 0.0364 (16) | 0.0040 (12) | 0.0147 (12) | 0.0054 (11) |
C10 | 0.0375 (15) | 0.0254 (14) | 0.0456 (18) | −0.0049 (12) | 0.0112 (13) | −0.0016 (12) |
C11 | 0.0372 (15) | 0.0372 (16) | 0.0307 (15) | −0.0055 (13) | 0.0036 (12) | −0.0078 (12) |
C12 | 0.0285 (12) | 0.0345 (14) | 0.0219 (13) | −0.0030 (11) | 0.0039 (10) | 0.0011 (11) |
C13 | 0.0199 (10) | 0.0192 (11) | 0.0161 (11) | −0.0007 (9) | 0.0042 (9) | 0.0008 (9) |
C14 | 0.0160 (10) | 0.0247 (12) | 0.0213 (12) | −0.0029 (9) | 0.0050 (9) | −0.0027 (9) |
C15 | 0.0206 (10) | 0.0173 (11) | 0.0194 (11) | 0.0009 (9) | 0.0061 (9) | 0.0001 (9) |
C16 | 0.0186 (10) | 0.0205 (11) | 0.0221 (12) | 0.0013 (9) | 0.0019 (9) | −0.0039 (9) |
C17 | 0.0248 (11) | 0.0199 (11) | 0.0177 (11) | −0.0007 (10) | 0.0061 (9) | 0.0002 (9) |
N1 | 0.0253 (10) | 0.0237 (10) | 0.0231 (11) | −0.0027 (9) | 0.0049 (8) | −0.0037 (8) |
N2 | 0.0323 (11) | 0.0272 (11) | 0.0254 (11) | −0.0007 (9) | 0.0072 (9) | −0.0026 (9) |
N3 | 0.0339 (11) | 0.0273 (11) | 0.0244 (11) | −0.0040 (10) | 0.0088 (9) | −0.0071 (9) |
N4 | 0.0258 (10) | 0.0259 (11) | 0.0216 (11) | −0.0009 (9) | 0.0021 (8) | 0.0008 (8) |
N5 | 0.0341 (11) | 0.0327 (12) | 0.0246 (12) | 0.0001 (10) | 0.0021 (9) | −0.0014 (9) |
N6 | 0.0400 (12) | 0.0320 (12) | 0.0193 (11) | 0.0057 (10) | 0.0059 (9) | 0.0037 (9) |
O1 | 0.0241 (8) | 0.0327 (10) | 0.0269 (10) | −0.0108 (8) | 0.0015 (7) | −0.0018 (8) |
O2 | 0.0642 (14) | 0.0554 (14) | 0.0225 (11) | −0.0254 (12) | −0.0085 (10) | 0.0031 (10) |
O3 | 0.0344 (10) | 0.0217 (9) | 0.0286 (10) | −0.0053 (7) | 0.0109 (8) | −0.0080 (7) |
O4 | 0.0276 (9) | 0.0270 (10) | 0.0480 (12) | −0.0011 (8) | 0.0183 (8) | −0.0125 (9) |
Zn1—O1 | 1.9469 (17) | C10—C11 | 1.410 (4) |
Zn1—O4i | 1.9572 (18) | C10—H10A | 0.9300 |
Zn1—N1 | 2.006 (2) | C11—C12 | 1.368 (4) |
Zn1—N4 | 2.038 (2) | C11—H11A | 0.9300 |
C1—N1 | 1.375 (3) | C12—H12A | 0.9300 |
C1—C6 | 1.389 (4) | C13—C14 | 1.378 (3) |
C1—C2 | 1.394 (4) | C13—C15ii | 1.407 (3) |
C2—C3 | 1.369 (4) | C13—C16 | 1.518 (3) |
C2—H2A | 0.9300 | C14—C15 | 1.397 (3) |
C3—C4 | 1.402 (5) | C14—H14A | 0.9300 |
C3—H3A | 0.9300 | C15—C13ii | 1.407 (3) |
C4—C5 | 1.361 (4) | C15—C17 | 1.496 (3) |
C4—H4A | 0.9300 | C16—O2 | 1.217 (3) |
C5—C6 | 1.398 (4) | C16—O1 | 1.273 (3) |
C5—H5A | 0.9300 | C17—O3 | 1.247 (3) |
C6—N3 | 1.357 (3) | C17—O4 | 1.271 (3) |
C7—N4 | 1.374 (3) | N1—N2 | 1.310 (3) |
C7—C8 | 1.388 (4) | N2—N3 | 1.319 (3) |
C7—C12 | 1.399 (4) | N3—H3B | 0.8600 |
C8—N6 | 1.364 (3) | N4—N5 | 1.316 (3) |
C8—C9 | 1.398 (4) | N5—N6 | 1.320 (3) |
C9—C10 | 1.367 (4) | N6—H6A | 0.8600 |
C9—H9A | 0.9300 | O4—Zn1i | 1.9572 (18) |
O1—Zn1—O4i | 98.38 (8) | C12—C11—H11A | 118.8 |
O1—Zn1—N1 | 121.89 (9) | C10—C11—H11A | 118.8 |
O4i—Zn1—N1 | 110.33 (9) | C11—C12—C7 | 116.5 (2) |
O1—Zn1—N4 | 108.98 (8) | C11—C12—H12A | 121.8 |
O4i—Zn1—N4 | 108.73 (9) | C7—C12—H12A | 121.8 |
N1—Zn1—N4 | 107.77 (8) | C14—C13—C15ii | 118.7 (2) |
N1—C1—C6 | 107.3 (2) | C14—C13—C16 | 117.4 (2) |
N1—C1—C2 | 132.0 (2) | C15ii—C13—C16 | 123.7 (2) |
C6—C1—C2 | 120.7 (2) | C13—C14—C15 | 122.5 (2) |
C3—C2—C1 | 116.3 (3) | C13—C14—H14A | 118.7 |
C3—C2—H2A | 121.9 | C15—C14—H14A | 118.7 |
C1—C2—H2A | 121.9 | C14—C15—C13ii | 118.7 (2) |
C2—C3—C4 | 122.5 (3) | C14—C15—C17 | 118.9 (2) |
C2—C3—H3A | 118.8 | C13ii—C15—C17 | 122.3 (2) |
C4—C3—H3A | 118.8 | O2—C16—O1 | 124.8 (2) |
C5—C4—C3 | 122.1 (3) | O2—C16—C13 | 118.9 (2) |
C5—C4—H4A | 118.9 | O1—C16—C13 | 116.2 (2) |
C3—C4—H4A | 118.9 | O3—C17—O4 | 124.0 (2) |
C4—C5—C6 | 115.5 (3) | O3—C17—C15 | 120.2 (2) |
C4—C5—H5A | 122.3 | O4—C17—C15 | 115.9 (2) |
C6—C5—H5A | 122.3 | N2—N1—C1 | 109.0 (2) |
N3—C6—C1 | 104.0 (2) | N2—N1—Zn1 | 119.61 (16) |
N3—C6—C5 | 133.0 (3) | C1—N1—Zn1 | 131.41 (17) |
C1—C6—C5 | 123.0 (3) | N1—N2—N3 | 108.0 (2) |
N4—C7—C8 | 107.2 (2) | N2—N3—C6 | 111.8 (2) |
N4—C7—C12 | 131.9 (2) | N2—N3—H3B | 124.1 |
C8—C7—C12 | 120.9 (2) | C6—N3—H3B | 124.1 |
N6—C8—C7 | 104.2 (2) | N5—N4—C7 | 109.2 (2) |
N6—C8—C9 | 133.2 (2) | N5—N4—Zn1 | 117.99 (16) |
C7—C8—C9 | 122.5 (2) | C7—N4—Zn1 | 132.52 (17) |
C10—C9—C8 | 116.1 (3) | N4—N5—N6 | 107.8 (2) |
C10—C9—H9A | 122.0 | N5—N6—C8 | 111.5 (2) |
C8—C9—H9A | 122.0 | N5—N6—H6A | 124.2 |
C9—C10—C11 | 121.6 (3) | C8—N6—H6A | 124.2 |
C9—C10—H10A | 119.2 | C16—O1—Zn1 | 115.31 (15) |
C11—C10—H10A | 119.2 | C17—O4—Zn1i | 122.15 (16) |
C12—C11—C10 | 122.4 (3) |
Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [Zn2(C10H2O8)(C6H5N3)4] |
Mr | 857.38 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 283 |
a, b, c (Å) | 7.7961 (16), 19.346 (4), 10.732 (2) |
β (°) | 101.78 (3) |
V (Å3) | 1584.6 (6) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.59 |
Crystal size (mm) | 0.26 × 0.22 × 0.17 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996; Blessing, 1995) |
Tmin, Tmax | 0.668, 0.764 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15373, 3628, 2924 |
Rint | 0.049 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.086, 1.05 |
No. of reflections | 3628 |
No. of parameters | 253 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.43, −0.40 |
Computer programs: SMART (Bruker, 1998), SMART, SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), SHELXTL.
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The rational design and synthesis of supramolecular complexes is of current interest in the field of supramolecular chemistry and crystal engineering. Benzotriazole (BTAH) is an attractive choice for multifunctional linking groups and has been inverstigated in the construction of metal-organic frameworks. Some structures of metal-organic polymers containing BTAH have been reported previously (Yuan & Zhou, 2004; Hu et al., 2005; Jones, Brechin, Collison, Raftery & Teat, 2002; Jones, Brecin, Collison, Harrison et al., 2002; Low et al., 2003; Meng et al., 2004). We present here the X-ray structure of the title compound, (I), which is a new example with a one-dimensional polymeric structure.
As shown in Fig. 1, the asymmetric unit of (I) contains one ZnII atom, two benzotriazole (BTAH) ligands and one-half of a benzene-1,2,4,5-tetracarboxylate (BTC) ligand. The ZnII atom is coordinated by two O atoms from two BTC ligands and two N atoms from two BTAH ligands, showing a distorted tetrahedral geometry. The Zn—O bond distances are 1.9469 (17) and 1.9572 (18) Å, while the Zn—N bond distances are 2.006 (2) and 2.038 (2) Å. Each BTC ligand is coordinated to four ZnII atoms and each BTAH ligand is coordinated to one ZnII atom. The dihedral angle between the planes of the two BTAH ligands is 61.739 (3)°.
The adjacent [Zn(BTAH)2] units are linked by the BTC ligands to form one-dimensional double chains running along the (100) direction like a molecular ladder (Fig. 2). The two BTAH ligands coordinated to one ZnII atom point out of the double chains. This orientation plays an important role in packing into a three-dimensional network through π–π stacking interactions between BTAH ligands. Firstly, the adjacent double chains are extended into a two-dimensional layer parallel to the [001] plane, and then a three-dimensional supramolecrlar network is formed by π–π stacking interactions. The face-to-face distances between neighboring parallel BTAH planes are 3.436 (3) and 3.571 (3) Å (Fig. 3).