Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806035197/lh2159sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536806035197/lh2159Isup2.hkl |
CCDC reference: 626342
Key indicators
- Single-crystal X-ray study
- T = 294 K
- Mean (C-C) = 0.008 Å
- R factor = 0.055
- wR factor = 0.152
- Data-to-parameter ratio = 11.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8 PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C4 - C5 ... 1.53 Ang.
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 2 ALERT type 3 Indicator that the structure quality may be low 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
Data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Bruker, 2001); program(s) used to refine structure: SHELXTL; molecular graphics: PLATON (Spek, 2003) and DIAMOND (Brandenburg & Berndt, 1999); software used to prepare material for publication: SHELXTL.
[Zn(C9H4O6)(C2H4N4)(H2O)]·2H2O | Z = 2 |
Mr = 411.65 | F(000) = 420 |
Triclinic, P1 | Dx = 1.726 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 7.730 (4) Å | Cell parameters from 1200 reflections |
b = 10.000 (6) Å | θ = 2.8–21.8° |
c = 11.533 (6) Å | µ = 1.61 mm−1 |
α = 85.672 (7)° | T = 294 K |
β = 71.590 (7)° | Block, colourless |
γ = 69.562 (7)° | 0.20 × 0.19 × 0.15 mm |
V = 792.0 (8) Å3 |
Bruker APEXII diffractometer | 2712 independent reflections |
Radiation source: fine-focus sealed tube | 1917 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.035 |
φ and ω scans | θmax = 25.0°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1997) | h = −9→9 |
Tmin = 0.719, Tmax = 0.786 | k = −11→6 |
4222 measured reflections | l = −13→13 |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.055 | w = 1/[σ2(Fo2) + (0.075P)2 + 1.0815P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.152 | (Δ/σ)max < 0.001 |
S = 1.05 | Δρmax = 0.85 e Å−3 |
2712 reflections | Δρmin = −0.68 e Å−3 |
227 parameters |
Experimental. Spectroscopic analysis: IR (KBr pellet, cm-1): 3455 (w), 3318 (m), 3148 (w), 3106 (w), 1700 (versus), 1613 (m), 1555 (s), 1432 (m), 1324 (m), 1239 (versus), 938 (m), 905 (m), 796 (w), 750 (s), 691 (s), 535 (m). Analysis, calculated for C22H28N8O18Zn2: C 60.73, H 3.71, N 9.66%; found: C 60.50, H 3.65, N 9.76%. |
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 | 0.73323 (9) | −0.01806 (7) | 0.84971 (6) | 0.0369 (3) | |
O1 | 0.5659 (6) | 0.2495 (5) | 0.7854 (4) | 0.0494 (12) | |
O2 | 0.5557 (6) | 0.1479 (4) | 0.9633 (4) | 0.0409 (10) | |
O3 | 0.0376 (6) | 0.7129 (4) | 0.7740 (4) | 0.0447 (11) | |
O4 | −0.1136 (5) | 0.8501 (4) | 0.9442 (4) | 0.0405 (10) | |
O5 | 0.0246 (6) | 0.6921 (5) | 1.3297 (4) | 0.0527 (12) | |
O6 | 0.2447 (7) | 0.4780 (5) | 1.3346 (4) | 0.0537 (12) | |
H6 | 0.2233 | 0.5069 | 1.4042 | 0.080* | |
O7 | 0.9452 (6) | 0.0281 (4) | 0.7172 (4) | 0.0483 (11) | |
H7A | 0.9082 | 0.1136 | 0.7045 | 0.072* | |
H7B | 1.0628 | −0.0162 | 0.7140 | 0.072* | |
N1 | 0.5848 (6) | −0.0683 (5) | 0.7573 (4) | 0.0365 (12) | |
N2 | 0.8312 (7) | −0.1671 (7) | 0.5710 (5) | 0.0574 (17) | |
H2A | 0.9207 | −0.1583 | 0.5958 | 0.069* | |
H2B | 0.8597 | −0.2029 | 0.4991 | 0.069* | |
N3 | 0.4970 (7) | −0.1281 (6) | 0.6126 (5) | 0.0442 (13) | |
H3' | 0.5036 | −0.1604 | 0.5437 | 0.053* | |
N4 | 0.3272 (7) | −0.0708 (6) | 0.7085 (5) | 0.0495 (14) | |
C1 | 0.5031 (8) | 0.2559 (6) | 0.8982 (5) | 0.0335 (13) | |
C2 | 0.3588 (7) | 0.3932 (6) | 0.9647 (5) | 0.0291 (12) | |
C3 | 0.2623 (7) | 0.5003 (6) | 0.8981 (5) | 0.0304 (12) | |
H3 | 0.2902 | 0.4855 | 0.8146 | 0.037* | |
C4 | 0.1267 (7) | 0.6271 (6) | 0.9549 (5) | 0.0314 (13) | |
C5 | 0.0121 (8) | 0.7369 (6) | 0.8828 (5) | 0.0331 (13) | |
C6 | 0.0909 (8) | 0.6505 (6) | 1.0780 (5) | 0.0350 (14) | |
H6A | 0.0006 | 0.7364 | 1.1164 | 0.042* | |
C7 | 0.1877 (8) | 0.5477 (6) | 1.1456 (5) | 0.0313 (13) | |
C8 | 0.1443 (8) | 0.5789 (6) | 1.2776 (5) | 0.0371 (14) | |
C9 | 0.3211 (8) | 0.4164 (6) | 1.0880 (5) | 0.0327 (13) | |
H9 | 0.3834 | 0.3456 | 1.1329 | 0.039* | |
C10 | 0.6495 (8) | −0.1255 (6) | 0.6436 (5) | 0.0374 (14) | |
C11 | 0.3888 (9) | −0.0374 (7) | 0.7901 (6) | 0.0470 (17) | |
H11 | 0.3056 | 0.0047 | 0.8658 | 0.056* | |
O8 | 0.5151 (8) | 0.2957 (6) | 0.5660 (5) | 0.0714 (15) | |
H8A | 0.5105 | 0.2733 | 0.6393 | 0.107* | |
H8B | 0.6183 | 0.3088 | 0.5203 | 0.107* | |
O9 | 0.2332 (7) | 0.5535 (5) | 0.5584 (4) | 0.0641 (15) | |
H9A | 0.1475 | 0.5976 | 0.6230 | 0.096* | |
H9B | 0.3203 | 0.4768 | 0.5674 | 0.096* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.0329 (4) | 0.0283 (4) | 0.0426 (4) | 0.0063 (3) | −0.0192 (3) | −0.0080 (3) |
O1 | 0.050 (3) | 0.038 (3) | 0.039 (3) | 0.011 (2) | −0.013 (2) | −0.006 (2) |
O2 | 0.046 (2) | 0.026 (2) | 0.041 (2) | 0.0065 (19) | −0.0208 (19) | −0.0031 (18) |
O3 | 0.049 (3) | 0.033 (2) | 0.042 (3) | 0.003 (2) | −0.020 (2) | −0.0036 (19) |
O4 | 0.036 (2) | 0.031 (2) | 0.044 (2) | 0.0069 (18) | −0.0163 (18) | −0.0069 (18) |
O5 | 0.058 (3) | 0.041 (3) | 0.039 (2) | 0.006 (2) | −0.012 (2) | −0.008 (2) |
O6 | 0.073 (3) | 0.041 (3) | 0.040 (3) | −0.003 (2) | −0.026 (2) | −0.001 (2) |
O7 | 0.038 (2) | 0.029 (2) | 0.070 (3) | 0.0022 (19) | −0.022 (2) | 0.004 (2) |
N1 | 0.028 (3) | 0.037 (3) | 0.035 (3) | 0.002 (2) | −0.009 (2) | −0.004 (2) |
N2 | 0.040 (3) | 0.083 (5) | 0.044 (3) | −0.015 (3) | −0.006 (3) | −0.024 (3) |
N3 | 0.045 (3) | 0.045 (3) | 0.043 (3) | −0.009 (3) | −0.021 (2) | −0.008 (2) |
N4 | 0.038 (3) | 0.058 (4) | 0.053 (3) | −0.011 (3) | −0.018 (3) | −0.009 (3) |
C1 | 0.029 (3) | 0.031 (3) | 0.040 (4) | −0.004 (3) | −0.016 (3) | −0.003 (3) |
C2 | 0.022 (3) | 0.020 (3) | 0.039 (3) | 0.000 (2) | −0.009 (2) | −0.003 (2) |
C3 | 0.031 (3) | 0.025 (3) | 0.032 (3) | −0.004 (2) | −0.012 (2) | −0.002 (2) |
C4 | 0.025 (3) | 0.026 (3) | 0.039 (3) | 0.000 (2) | −0.013 (2) | −0.002 (2) |
C5 | 0.026 (3) | 0.028 (3) | 0.041 (3) | −0.001 (2) | −0.013 (2) | −0.002 (3) |
C6 | 0.028 (3) | 0.022 (3) | 0.046 (4) | 0.003 (2) | −0.011 (2) | −0.002 (2) |
C7 | 0.032 (3) | 0.023 (3) | 0.036 (3) | −0.006 (2) | −0.012 (2) | −0.001 (2) |
C8 | 0.040 (3) | 0.025 (3) | 0.045 (3) | −0.005 (3) | −0.016 (3) | −0.002 (3) |
C9 | 0.032 (3) | 0.025 (3) | 0.039 (3) | −0.004 (2) | −0.016 (3) | 0.001 (2) |
C10 | 0.037 (3) | 0.034 (3) | 0.039 (3) | −0.007 (3) | −0.014 (3) | −0.005 (3) |
C11 | 0.037 (3) | 0.051 (4) | 0.042 (4) | −0.003 (3) | −0.010 (3) | −0.006 (3) |
O8 | 0.091 (4) | 0.064 (4) | 0.056 (3) | −0.007 (3) | −0.038 (3) | −0.009 (3) |
O9 | 0.064 (3) | 0.059 (3) | 0.052 (3) | 0.007 (3) | −0.023 (2) | −0.012 (2) |
Zn1—O4i | 1.959 (4) | N3—N4 | 1.389 (7) |
Zn1—O2 | 1.989 (4) | N3—H3' | 0.8600 |
Zn1—N1 | 1.990 (5) | N4—C11 | 1.291 (8) |
Zn1—O7 | 2.018 (4) | C1—C2 | 1.505 (7) |
O1—C1 | 1.235 (7) | C2—C9 | 1.380 (8) |
O2—C1 | 1.289 (7) | C2—C3 | 1.405 (7) |
O3—C5 | 1.236 (6) | C3—C4 | 1.378 (7) |
O4—C5 | 1.282 (6) | C3—H3 | 0.9300 |
O4—Zn1ii | 1.959 (4) | C4—C6 | 1.379 (8) |
O5—C8 | 1.232 (7) | C4—C5 | 1.527 (7) |
O6—C8 | 1.315 (7) | C6—C7 | 1.391 (8) |
O6—H6 | 0.8200 | C6—H6A | 0.9300 |
O7—H7A | 0.8200 | C7—C9 | 1.408 (7) |
O7—H7B | 0.8501 | C7—C8 | 1.485 (8) |
N1—C10 | 1.340 (7) | C9—H9 | 0.9300 |
N1—C11 | 1.366 (8) | C11—H11 | 0.9300 |
N2—C10 | 1.322 (7) | O8—H8A | 0.8506 |
N2—H2A | 0.8600 | O8—H8B | 0.8532 |
N2—H2B | 0.8600 | O9—H9A | 0.8498 |
N3—C10 | 1.345 (7) | O9—H9B | 0.8508 |
O4i—Zn1—O2 | 105.53 (16) | C4—C3—H3 | 119.6 |
O4i—Zn1—N1 | 125.53 (19) | C2—C3—H3 | 119.6 |
O2—Zn1—N1 | 108.81 (17) | C3—C4—C6 | 119.3 (5) |
O4i—Zn1—O7 | 100.41 (17) | C3—C4—C5 | 119.9 (5) |
O2—Zn1—O7 | 112.91 (18) | C6—C4—C5 | 120.8 (5) |
N1—Zn1—O7 | 103.43 (19) | O3—C5—O4 | 123.9 (5) |
C1—O2—Zn1 | 107.8 (3) | O3—C5—C4 | 120.8 (5) |
C5—O4—Zn1ii | 113.5 (3) | O4—C5—C4 | 115.3 (5) |
C8—O6—H6 | 109.5 | C4—C6—C7 | 121.1 (5) |
Zn1—O7—H7A | 109.5 | C4—C6—H6A | 119.5 |
Zn1—O7—H7B | 118.8 | C7—C6—H6A | 119.5 |
H7A—O7—H7B | 120.5 | C6—C7—C9 | 119.4 (5) |
C10—N1—C11 | 103.7 (5) | C6—C7—C8 | 118.8 (5) |
C10—N1—Zn1 | 128.4 (4) | C9—C7—C8 | 121.8 (5) |
C11—N1—Zn1 | 127.5 (4) | O5—C8—O6 | 122.4 (5) |
C10—N2—H2A | 120.0 | O5—C8—C7 | 122.4 (5) |
C10—N2—H2B | 120.0 | O6—C8—C7 | 115.2 (5) |
H2A—N2—H2B | 120.0 | C2—C9—C7 | 119.6 (5) |
C10—N3—N4 | 109.7 (5) | C2—C9—H9 | 120.2 |
C10—N3—H3' | 125.1 | C7—C9—H9 | 120.2 |
N4—N3—H3' | 125.1 | N2—C10—N1 | 126.3 (5) |
C11—N4—N3 | 102.7 (5) | N2—C10—N3 | 125.0 (5) |
O1—C1—O2 | 122.4 (5) | N1—C10—N3 | 108.7 (5) |
O1—C1—C2 | 120.1 (5) | N4—C11—N1 | 115.1 (5) |
O2—C1—C2 | 117.5 (5) | N4—C11—H11 | 122.4 |
C9—C2—C3 | 119.6 (5) | N1—C11—H11 | 122.4 |
C9—C2—C1 | 121.8 (5) | H8A—O8—H8B | 117.1 |
C3—C2—C1 | 118.6 (5) | H9A—O9—H9B | 117.0 |
C4—C3—C2 | 120.9 (5) | ||
O4i—Zn1—O2—C1 | 157.7 (4) | C3—C4—C5—O4 | 178.5 (5) |
N1—Zn1—O2—C1 | −65.3 (4) | C6—C4—C5—O4 | 1.1 (8) |
O7—Zn1—O2—C1 | 48.9 (4) | C3—C4—C6—C7 | −0.7 (9) |
O4i—Zn1—N1—C10 | −84.4 (6) | C5—C4—C6—C7 | 176.7 (5) |
O2—Zn1—N1—C10 | 149.4 (5) | C4—C6—C7—C9 | −1.5 (9) |
O7—Zn1—N1—C10 | 29.1 (5) | C4—C6—C7—C8 | 179.7 (5) |
O4i—Zn1—N1—C11 | 103.7 (5) | C6—C7—C8—O5 | 0.6 (9) |
O2—Zn1—N1—C11 | −22.5 (6) | C9—C7—C8—O5 | −178.3 (6) |
O7—Zn1—N1—C11 | −142.8 (5) | C6—C7—C8—O6 | −178.5 (6) |
C10—N3—N4—C11 | 0.2 (7) | C9—C7—C8—O6 | 2.6 (8) |
Zn1—O2—C1—O1 | −2.8 (7) | C3—C2—C9—C7 | −0.6 (8) |
Zn1—O2—C1—C2 | 176.8 (4) | C1—C2—C9—C7 | 178.7 (5) |
O1—C1—C2—C9 | −163.9 (5) | C6—C7—C9—C2 | 2.1 (8) |
O2—C1—C2—C9 | 16.5 (8) | C8—C7—C9—C2 | −179.0 (5) |
O1—C1—C2—C3 | 15.5 (8) | C11—N1—C10—N2 | 176.9 (7) |
O2—C1—C2—C3 | −164.1 (5) | Zn1—N1—C10—N2 | 3.5 (10) |
C9—C2—C3—C4 | −1.6 (9) | C11—N1—C10—N3 | −0.3 (7) |
C1—C2—C3—C4 | 179.0 (5) | Zn1—N1—C10—N3 | −173.7 (4) |
C2—C3—C4—C6 | 2.3 (9) | N4—N3—C10—N2 | −177.2 (6) |
C2—C3—C4—C5 | −175.1 (5) | N4—N3—C10—N1 | 0.1 (7) |
Zn1ii—O4—C5—O3 | 0.9 (8) | N3—N4—C11—N1 | −0.4 (8) |
Zn1ii—O4—C5—C4 | −176.6 (4) | C10—N1—C11—N4 | 0.5 (8) |
C3—C4—C5—O3 | 0.9 (9) | Zn1—N1—C11—N4 | 174.0 (5) |
C6—C4—C5—O3 | −176.4 (6) |
Symmetry codes: (i) x+1, y−1, z; (ii) x−1, y+1, z. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O3i | 0.86 | 2.58 | 3.173 (8) | 127 |
N2—H2A···O7 | 0.86 | 2.51 | 3.173 (8) | 135 |
N2—H2B···O5iii | 0.86 | 2.08 | 2.908 (7) | 160 |
N3—H3′···O8iv | 0.86 | 1.99 | 2.795 (8) | 155 |
O6—H6···O9v | 0.82 | 1.90 | 2.710 (7) | 167 |
O7—H7A···O1 | 0.82 | 2.42 | 2.897 (7) | 118 |
O7—H7A···O5vi | 0.82 | 2.16 | 2.885 (6) | 148 |
O7—H7B···N4vii | 0.85 | 1.90 | 2.738 (8) | 166 |
O8—H8A···O1 | 0.85 | 1.84 | 2.664 (7) | 161 |
O8—H8B···O9viii | 0.85 | 2.07 | 2.842 (8) | 150 |
O9—H9A···O3 | 0.85 | 1.94 | 2.748 (6) | 158 |
O9—H9B···O8 | 0.85 | 1.91 | 2.751 (8) | 172 |
Symmetry codes: (i) x+1, y−1, z; (iii) x+1, y−1, z−1; (iv) −x+1, −y, −z+1; (v) x, y, z+1; (vi) −x+1, −y+1, −z+2; (vii) x+1, y, z; (viii) −x+1, −y+1, −z+1. |