Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807054608/sg2196sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807054608/sg2196Isup2.hkl |
CCDC reference: 665043
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C) = 0.006 Å
- Disorder in solvent or counterion
- R factor = 0.042
- wR factor = 0.125
- Data-to-parameter ratio = 12.7
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT417_ALERT_2_B Short Inter D-H..H-D H6B .. H7D .. 2.07 Ang. PLAT417_ALERT_2_B Short Inter D-H..H-D H6B .. H7E .. 1.97 Ang.
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 ..................... 0.98 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O1 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for O3 PLAT302_ALERT_4_C Anion/Solvent Disorder ......................... 25.00 Perc. PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C1 - C2 ... 1.53 Ang. PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C12 - C13 ... 1.53 Ang. PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 1 N4 -ZN1 -N1 -C6 18.00 0.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 6 N4 -ZN1 -N1 -C2 -5.00 2.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 25 N1 -ZN1 -N4 -C17 -84.00 2.00 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 30 N1 -ZN1 -N4 -C13 88.00 2.00 1.555 1.555 1.555 1.555
0 ALERT level A = In general: serious problem 2 ALERT level B = Potentially serious problem 13 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 6 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 7 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinic acid, and ZnCl2. 6H2O were available commercially and were used without further purification. Equimolar 6-(3,5-dimethyl-1H-pyrazol-1-yl)picolinic acid (1 mmol, 217 mg) was dissolved in anhydrous alcohol (15 ml). The mixture was stirred to give a clear solution, To this solution was added ZnCl2.6H2O (0.5 mmol, 119 mg) in anhydrous alcohol (10 ml). After keeping the resulting solution in air to evaporate about half of the solvents, dark red prisms of the title compound were formed. The crystals were isolated, washed with alcohol three times and dried in a vacuum desiccator using silica gel (Yield 75%). Elemental analysis: found: C, 47.78; H, 4.85; N, 15.13; O, 20.39; calc. for C22H26ZnN6O7: C, 47.88; H, 4.75; N, 15.23; O, 20.29
All the H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with N—H and C—H distances of 0.90 Å and 0.96 Å, respectively. They were treated as riding atoms, with Uiso(H) = 1.2Ueq(C), Uiso(H) = 1.2Ueq(N) and Uiso(H) = 1.5Ueq(O).
Data collection: SMART (Siemens, 1996); cell refinement: SMART (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL (Sheldrick, 1997b).
[Zn(C11H10N3O2)2]·3H2O | Z = 2 |
Mr = 551.86 | F(000) = 572 |
Triclinic, P1 | Dx = 1.490 Mg m−3 |
a = 9.8071 (9) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.8388 (12) Å | Cell parameters from 3006 reflections |
c = 12.6766 (16) Å | θ = 2.2–25.9° |
α = 71.334 (2)° | µ = 1.05 mm−1 |
β = 74.505 (2)° | T = 298 K |
γ = 84.772 (3)° | Block, colorless |
V = 1230.2 (2) Å3 | 0.50 × 0.48 × 0.34 mm |
Bruker SMART CCD area-detector diffractometer | 4251 independent reflections |
Radiation source: fine-focus sealed tube | 3192 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.021 |
phi and ω scans | θmax = 25.0°, θmin = 1.8° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −11→11 |
Tmin = 0.621, Tmax = 0.716 | k = −12→12 |
6315 measured reflections | l = −15→12 |
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)] = 0.042 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.125 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0638P)2 + 0.5328P] where P = (Fo2 + 2Fc2)/3 |
4251 reflections | (Δ/σ)max = 0.001 |
334 parameters | Δρmax = 0.50 e Å−3 |
0 restraints | Δρmin = −0.38 e Å−3 |
[Zn(C11H10N3O2)2]·3H2O | γ = 84.772 (3)° |
Mr = 551.86 | V = 1230.2 (2) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.8071 (9) Å | Mo Kα radiation |
b = 10.8388 (12) Å | µ = 1.05 mm−1 |
c = 12.6766 (16) Å | T = 298 K |
α = 71.334 (2)° | 0.50 × 0.48 × 0.34 mm |
β = 74.505 (2)° |
Bruker SMART CCD area-detector diffractometer | 4251 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3192 reflections with I > 2σ(I) |
Tmin = 0.621, Tmax = 0.716 | Rint = 0.021 |
6315 measured reflections |
R[F2 > 2σ(F2)] = 0.042 | 0 restraints |
wR(F2) = 0.125 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.50 e Å−3 |
4251 reflections | Δρmin = −0.38 e Å−3 |
334 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 | Occ. (<1) | |
Zn1 | 0.78562 (4) | 0.71982 (4) | 0.72699 (4) | 0.04776 (17) | |
N1 | 0.8809 (3) | 0.8979 (2) | 0.6879 (2) | 0.0383 (6) | |
N2 | 1.0937 (3) | 0.8039 (3) | 0.6297 (2) | 0.0415 (6) | |
N3 | 1.0155 (3) | 0.6935 (3) | 0.6573 (2) | 0.0432 (7) | |
N4 | 0.6810 (3) | 0.5449 (2) | 0.7692 (2) | 0.0382 (6) | |
N5 | 0.7234 (3) | 0.4926 (3) | 0.9470 (2) | 0.0445 (7) | |
N6 | 0.7831 (3) | 0.6137 (3) | 0.9073 (3) | 0.0500 (7) | |
O1 | 0.6140 (3) | 0.8407 (3) | 0.7764 (3) | 0.0775 (9) | |
O2 | 0.5565 (3) | 1.0410 (3) | 0.7860 (3) | 0.0882 (10) | |
O3 | 0.7335 (3) | 0.7301 (3) | 0.5734 (2) | 0.0631 (7) | |
O4 | 0.6151 (3) | 0.6316 (3) | 0.4964 (2) | 0.0604 (7) | |
O5 | 0.6801 (4) | 0.8398 (4) | 0.2929 (3) | 0.1290 (17) | |
H5A | 0.6557 | 0.7771 | 0.3548 | 0.155* | |
H5B | 0.6060 | 0.8730 | 0.2720 | 0.155* | |
O6 | 0.0977 (5) | 0.0193 (5) | 0.8593 (4) | 0.1492 (18) | |
H6A | 0.1701 | 0.0622 | 0.8137 | 0.179* | |
H6B | 0.1187 | −0.0245 | 0.9216 | 0.179* | |
O7 | 0.8467 (7) | 0.1337 (7) | 0.9299 (5) | 0.095 (2) | 0.50 |
H7D | 0.7748 | 0.0855 | 0.9498 | 0.113* | 0.50 |
H7E | 0.9202 | 0.0906 | 0.9094 | 0.113* | 0.50 |
O8 | 0.6242 (9) | 0.0134 (8) | 0.9945 (6) | 0.131 (3) | 0.50 |
H8A | 0.5892 | 0.0190 | 0.9386 | 0.157* | 0.50 |
H8B | 0.5582 | −0.0035 | 1.0561 | 0.157* | 0.50 |
C1 | 0.6401 (4) | 0.9559 (4) | 0.7605 (4) | 0.0607 (10) | |
C2 | 0.7947 (4) | 0.9962 (3) | 0.7060 (3) | 0.0471 (8) | |
C3 | 0.8450 (5) | 1.1204 (4) | 0.6748 (4) | 0.0624 (11) | |
H3 | 0.7846 | 1.1883 | 0.6876 | 0.075* | |
C4 | 0.9862 (5) | 1.1418 (4) | 0.6245 (4) | 0.0698 (12) | |
H4 | 1.0222 | 1.2254 | 0.6014 | 0.084* | |
C5 | 1.0746 (4) | 1.0412 (3) | 0.6078 (3) | 0.0586 (10) | |
H5 | 1.1709 | 1.0549 | 0.5745 | 0.070* | |
C6 | 1.0172 (3) | 0.9183 (3) | 0.6419 (3) | 0.0401 (7) | |
C7 | 1.3505 (4) | 0.8774 (4) | 0.5519 (4) | 0.0664 (11) | |
H7A | 1.4403 | 0.8362 | 0.5319 | 0.100* | |
H7B | 1.3475 | 0.9097 | 0.6147 | 0.100* | |
H7C | 1.3378 | 0.9484 | 0.4867 | 0.100* | |
C8 | 1.2346 (4) | 0.7804 (4) | 0.5869 (3) | 0.0479 (8) | |
C9 | 1.2439 (4) | 0.6538 (4) | 0.5886 (3) | 0.0542 (9) | |
H9 | 1.3260 | 0.6091 | 0.5650 | 0.065* | |
C10 | 1.1074 (4) | 0.6037 (3) | 0.6322 (3) | 0.0466 (8) | |
C11 | 1.0586 (5) | 0.4695 (4) | 0.6528 (4) | 0.0672 (11) | |
H11A | 1.0213 | 0.4290 | 0.7338 | 0.101* | |
H11B | 1.1370 | 0.4190 | 0.6243 | 0.101* | |
H11C | 0.9862 | 0.4742 | 0.6135 | 0.101* | |
C12 | 0.6603 (3) | 0.6400 (4) | 0.5754 (3) | 0.0475 (8) | |
C13 | 0.6244 (3) | 0.5298 (3) | 0.6900 (3) | 0.0409 (8) | |
C14 | 0.5401 (4) | 0.4242 (3) | 0.7133 (3) | 0.0506 (9) | |
H14 | 0.5027 | 0.4128 | 0.6570 | 0.061* | |
C15 | 0.5132 (4) | 0.3362 (3) | 0.8224 (4) | 0.0581 (10) | |
H15 | 0.4557 | 0.2649 | 0.8403 | 0.070* | |
C16 | 0.5703 (4) | 0.3526 (3) | 0.9051 (4) | 0.0562 (10) | |
H16 | 0.5516 | 0.2943 | 0.9792 | 0.067* | |
C17 | 0.6566 (3) | 0.4596 (3) | 0.8736 (3) | 0.0410 (8) | |
C18 | 0.6907 (5) | 0.2913 (5) | 1.1241 (4) | 0.0839 (15) | |
H18A | 0.5892 | 0.2888 | 1.1455 | 0.126* | |
H18B | 0.7252 | 0.2645 | 1.1922 | 0.126* | |
H18C | 0.7268 | 0.2334 | 1.0793 | 0.126* | |
C19 | 0.7389 (4) | 0.4274 (4) | 1.0543 (3) | 0.0550 (9) | |
C20 | 0.8090 (5) | 0.5092 (4) | 1.0815 (4) | 0.0683 (11) | |
H20 | 0.8359 | 0.4921 | 1.1499 | 0.082* | |
C21 | 0.8344 (4) | 0.6234 (4) | 0.9900 (3) | 0.0586 (10) | |
C22 | 0.9040 (6) | 0.7455 (5) | 0.9796 (4) | 0.0874 (15) | |
H22A | 0.9557 | 0.7839 | 0.9012 | 0.131* | |
H22B | 0.9678 | 0.7251 | 1.0286 | 0.131* | |
H22C | 0.8331 | 0.8057 | 1.0022 | 0.131* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Zn1 | 0.0398 (3) | 0.0390 (2) | 0.0616 (3) | −0.01119 (17) | −0.00741 (19) | −0.01302 (19) |
N1 | 0.0382 (15) | 0.0338 (14) | 0.0419 (15) | −0.0030 (11) | −0.0058 (12) | −0.0131 (12) |
N2 | 0.0337 (15) | 0.0418 (15) | 0.0484 (17) | −0.0082 (12) | −0.0060 (12) | −0.0147 (13) |
N3 | 0.0382 (15) | 0.0382 (15) | 0.0549 (17) | −0.0030 (12) | −0.0093 (13) | −0.0181 (13) |
N4 | 0.0299 (14) | 0.0380 (14) | 0.0459 (16) | −0.0034 (11) | −0.0060 (12) | −0.0139 (13) |
N5 | 0.0404 (16) | 0.0452 (16) | 0.0454 (17) | −0.0098 (13) | −0.0081 (13) | −0.0104 (13) |
N6 | 0.0505 (18) | 0.0460 (17) | 0.0533 (18) | −0.0136 (14) | −0.0101 (14) | −0.0139 (14) |
O1 | 0.0384 (15) | 0.0589 (18) | 0.116 (3) | −0.0053 (13) | 0.0062 (15) | −0.0210 (17) |
O2 | 0.072 (2) | 0.077 (2) | 0.099 (2) | 0.0321 (17) | −0.0020 (18) | −0.0289 (18) |
O3 | 0.0582 (16) | 0.0646 (17) | 0.0608 (17) | −0.0278 (13) | −0.0192 (13) | −0.0005 (13) |
O4 | 0.0574 (16) | 0.0719 (18) | 0.0553 (16) | −0.0067 (13) | −0.0205 (13) | −0.0173 (14) |
O5 | 0.080 (2) | 0.153 (4) | 0.115 (3) | −0.041 (2) | −0.044 (2) | 0.038 (3) |
O6 | 0.129 (4) | 0.166 (5) | 0.126 (4) | −0.039 (3) | −0.019 (3) | −0.010 (3) |
O7 | 0.091 (5) | 0.140 (6) | 0.073 (4) | 0.026 (4) | −0.025 (4) | −0.064 (4) |
O8 | 0.148 (7) | 0.145 (7) | 0.065 (5) | 0.030 (6) | 0.015 (5) | −0.028 (5) |
C1 | 0.053 (2) | 0.054 (2) | 0.063 (3) | 0.0125 (19) | −0.0038 (19) | −0.014 (2) |
C2 | 0.054 (2) | 0.0384 (19) | 0.047 (2) | 0.0061 (16) | −0.0117 (17) | −0.0136 (16) |
C3 | 0.083 (3) | 0.038 (2) | 0.070 (3) | 0.006 (2) | −0.020 (2) | −0.0228 (19) |
C4 | 0.086 (3) | 0.041 (2) | 0.083 (3) | −0.020 (2) | −0.014 (3) | −0.021 (2) |
C5 | 0.053 (2) | 0.050 (2) | 0.073 (3) | −0.0167 (18) | −0.006 (2) | −0.022 (2) |
C6 | 0.0387 (18) | 0.0407 (18) | 0.0419 (19) | −0.0071 (14) | −0.0069 (15) | −0.0147 (15) |
C7 | 0.036 (2) | 0.080 (3) | 0.070 (3) | −0.0162 (19) | −0.0033 (18) | −0.010 (2) |
C8 | 0.0353 (19) | 0.065 (2) | 0.040 (2) | −0.0056 (16) | −0.0071 (15) | −0.0127 (17) |
C9 | 0.041 (2) | 0.066 (3) | 0.054 (2) | 0.0098 (18) | −0.0102 (17) | −0.0214 (19) |
C10 | 0.046 (2) | 0.047 (2) | 0.051 (2) | 0.0061 (16) | −0.0133 (16) | −0.0218 (17) |
C11 | 0.067 (3) | 0.050 (2) | 0.091 (3) | 0.0059 (19) | −0.021 (2) | −0.032 (2) |
C12 | 0.0327 (18) | 0.057 (2) | 0.053 (2) | −0.0024 (16) | −0.0107 (16) | −0.0168 (17) |
C13 | 0.0324 (17) | 0.0436 (18) | 0.051 (2) | 0.0008 (14) | −0.0089 (15) | −0.0212 (16) |
C14 | 0.048 (2) | 0.045 (2) | 0.069 (3) | −0.0004 (16) | −0.0194 (18) | −0.0272 (19) |
C15 | 0.059 (2) | 0.0376 (19) | 0.080 (3) | −0.0138 (17) | −0.023 (2) | −0.0139 (19) |
C16 | 0.058 (2) | 0.0375 (19) | 0.067 (3) | −0.0127 (17) | −0.0168 (19) | −0.0049 (18) |
C17 | 0.0358 (18) | 0.0367 (17) | 0.048 (2) | −0.0010 (14) | −0.0079 (15) | −0.0117 (15) |
C18 | 0.096 (4) | 0.083 (3) | 0.060 (3) | −0.036 (3) | −0.026 (3) | 0.011 (2) |
C19 | 0.051 (2) | 0.061 (2) | 0.047 (2) | −0.0128 (18) | −0.0057 (17) | −0.0093 (18) |
C20 | 0.072 (3) | 0.086 (3) | 0.049 (2) | −0.018 (2) | −0.019 (2) | −0.015 (2) |
C21 | 0.055 (2) | 0.068 (3) | 0.058 (2) | −0.0155 (19) | −0.0137 (19) | −0.023 (2) |
C22 | 0.105 (4) | 0.082 (3) | 0.088 (3) | −0.035 (3) | −0.036 (3) | −0.025 (3) |
Zn1—N1 | 2.077 (3) | C4—C5 | 1.364 (6) |
Zn1—N4 | 2.084 (3) | C4—H4 | 0.9300 |
Zn1—O3 | 2.109 (3) | C5—C6 | 1.385 (4) |
Zn1—O1 | 2.122 (3) | C5—H5 | 0.9300 |
Zn1—N6 | 2.200 (3) | C7—C8 | 1.498 (5) |
Zn1—N3 | 2.219 (3) | C7—H7A | 0.9600 |
N1—C6 | 1.315 (4) | C7—H7B | 0.9600 |
N1—C2 | 1.339 (4) | C7—H7C | 0.9600 |
N2—C8 | 1.376 (4) | C8—C9 | 1.361 (5) |
N2—N3 | 1.377 (3) | C9—C10 | 1.392 (5) |
N2—C6 | 1.420 (4) | C9—H9 | 0.9300 |
N3—C10 | 1.322 (4) | C10—C11 | 1.493 (5) |
N4—C17 | 1.323 (4) | C11—H11A | 0.9600 |
N4—C13 | 1.328 (4) | C11—H11B | 0.9600 |
N5—C19 | 1.359 (5) | C11—H11C | 0.9600 |
N5—N6 | 1.371 (4) | C12—C13 | 1.534 (5) |
N5—C17 | 1.416 (4) | C13—C14 | 1.380 (5) |
N6—C21 | 1.313 (5) | C14—C15 | 1.378 (5) |
O1—C1 | 1.239 (5) | C14—H14 | 0.9300 |
O2—C1 | 1.240 (5) | C15—C16 | 1.377 (5) |
O3—C12 | 1.253 (4) | C15—H15 | 0.9300 |
O4—C12 | 1.230 (4) | C16—C17 | 1.387 (5) |
O5—H5A | 0.8500 | C16—H16 | 0.9300 |
O5—H5B | 0.8500 | C18—C19 | 1.500 (5) |
O6—H6A | 0.8500 | C18—H18A | 0.9600 |
O6—H6B | 0.8499 | C18—H18B | 0.9600 |
O7—H7D | 0.8499 | C18—H18C | 0.9600 |
O7—H7E | 0.8499 | C19—C20 | 1.346 (6) |
O8—H8A | 0.8500 | C20—C21 | 1.387 (6) |
O8—H8B | 0.8500 | C20—H20 | 0.9300 |
C1—C2 | 1.528 (5) | C21—C22 | 1.496 (5) |
C2—C3 | 1.374 (5) | C22—H22A | 0.9600 |
C3—C4 | 1.367 (6) | C22—H22B | 0.9600 |
C3—H3 | 0.9300 | C22—H22C | 0.9600 |
N1—Zn1—N4 | 177.31 (10) | H7A—C7—H7B | 109.5 |
N1—Zn1—O3 | 103.44 (10) | C8—C7—H7C | 109.5 |
N4—Zn1—O3 | 76.71 (10) | H7A—C7—H7C | 109.5 |
N1—Zn1—O1 | 76.63 (10) | H7B—C7—H7C | 109.5 |
N4—Zn1—O1 | 100.68 (11) | C9—C8—N2 | 106.2 (3) |
O3—Zn1—O1 | 93.81 (12) | C9—C8—C7 | 129.0 (4) |
N1—Zn1—N6 | 106.66 (10) | N2—C8—C7 | 124.7 (3) |
N4—Zn1—N6 | 73.18 (10) | C8—C9—C10 | 107.1 (3) |
O3—Zn1—N6 | 149.89 (10) | C8—C9—H9 | 126.5 |
O1—Zn1—N6 | 92.03 (12) | C10—C9—H9 | 126.5 |
N1—Zn1—N3 | 73.01 (10) | N3—C10—C9 | 110.7 (3) |
N4—Zn1—N3 | 109.68 (10) | N3—C10—C11 | 120.3 (3) |
O3—Zn1—N3 | 94.08 (10) | C9—C10—C11 | 129.0 (3) |
O1—Zn1—N3 | 149.62 (11) | C10—C11—H11A | 109.5 |
N6—Zn1—N3 | 95.67 (11) | C10—C11—H11B | 109.5 |
C6—N1—C2 | 120.2 (3) | H11A—C11—H11B | 109.5 |
C6—N1—Zn1 | 123.3 (2) | C10—C11—H11C | 109.5 |
C2—N1—Zn1 | 116.4 (2) | H11A—C11—H11C | 109.5 |
C8—N2—N3 | 110.3 (3) | H11B—C11—H11C | 109.5 |
C8—N2—C6 | 132.7 (3) | O4—C12—O3 | 127.0 (3) |
N3—N2—C6 | 116.8 (2) | O4—C12—C13 | 117.7 (3) |
C10—N3—N2 | 105.8 (3) | O3—C12—C13 | 115.3 (3) |
C10—N3—Zn1 | 140.6 (2) | N4—C13—C14 | 121.2 (3) |
N2—N3—Zn1 | 113.60 (18) | N4—C13—C12 | 113.6 (3) |
C17—N4—C13 | 120.8 (3) | C14—C13—C12 | 125.2 (3) |
C17—N4—Zn1 | 122.4 (2) | C15—C14—C13 | 118.1 (3) |
C13—N4—Zn1 | 116.4 (2) | C15—C14—H14 | 120.9 |
C19—N5—N6 | 110.9 (3) | C13—C14—H14 | 120.9 |
C19—N5—C17 | 132.4 (3) | C16—C15—C14 | 120.8 (3) |
N6—N5—C17 | 116.7 (3) | C16—C15—H15 | 119.6 |
C21—N6—N5 | 105.8 (3) | C14—C15—H15 | 119.6 |
C21—N6—Zn1 | 139.6 (3) | C15—C16—C17 | 117.4 (3) |
N5—N6—Zn1 | 114.1 (2) | C15—C16—H16 | 121.3 |
C1—O1—Zn1 | 117.6 (2) | C17—C16—H16 | 121.3 |
C12—O3—Zn1 | 117.6 (2) | N4—C17—C16 | 121.8 (3) |
H5A—O5—H5B | 108.5 | N4—C17—N5 | 112.9 (3) |
H6A—O6—H6B | 108.5 | C16—C17—N5 | 125.3 (3) |
H7D—O7—H7E | 108.6 | C19—C18—H18A | 109.5 |
H8A—O8—H8B | 108.7 | C19—C18—H18B | 109.5 |
O1—C1—O2 | 127.8 (4) | H18A—C18—H18B | 109.5 |
O1—C1—C2 | 115.7 (3) | C19—C18—H18C | 109.5 |
O2—C1—C2 | 116.5 (4) | H18A—C18—H18C | 109.5 |
N1—C2—C3 | 121.2 (3) | H18B—C18—H18C | 109.5 |
N1—C2—C1 | 113.5 (3) | C20—C19—N5 | 105.4 (3) |
C3—C2—C1 | 125.3 (3) | C20—C19—C18 | 128.3 (4) |
C4—C3—C2 | 118.4 (4) | N5—C19—C18 | 126.3 (4) |
C4—C3—H3 | 120.8 | C19—C20—C21 | 108.2 (4) |
C2—C3—H3 | 120.8 | C19—C20—H20 | 125.9 |
C5—C4—C3 | 120.4 (4) | C21—C20—H20 | 125.9 |
C5—C4—H4 | 119.8 | N6—C21—C20 | 109.7 (3) |
C3—C4—H4 | 119.8 | N6—C21—C22 | 121.4 (4) |
C4—C5—C6 | 118.2 (4) | C20—C21—C22 | 128.9 (4) |
C4—C5—H5 | 120.9 | C21—C22—H22A | 109.5 |
C6—C5—H5 | 120.9 | C21—C22—H22B | 109.5 |
N1—C6—C5 | 121.5 (3) | H22A—C22—H22B | 109.5 |
N1—C6—N2 | 113.0 (3) | C21—C22—H22C | 109.5 |
C5—C6—N2 | 125.4 (3) | H22A—C22—H22C | 109.5 |
C8—C7—H7A | 109.5 | H22B—C22—H22C | 109.5 |
C8—C7—H7B | 109.5 | ||
N4—Zn1—N1—C6 | 179 (100) | O2—C1—C2—N1 | 175.7 (3) |
O3—Zn1—N1—C6 | −88.5 (3) | O1—C1—C2—C3 | 175.9 (4) |
O1—Zn1—N1—C6 | −179.2 (3) | O2—C1—C2—C3 | −5.6 (6) |
N6—Zn1—N1—C6 | 92.7 (3) | N1—C2—C3—C4 | 0.0 (6) |
N3—Zn1—N1—C6 | 1.7 (2) | C1—C2—C3—C4 | −178.6 (4) |
N4—Zn1—N1—C2 | −5 (2) | C2—C3—C4—C5 | −1.2 (6) |
O3—Zn1—N1—C2 | 87.9 (2) | C3—C4—C5—C6 | 0.8 (6) |
O1—Zn1—N1—C2 | −2.8 (2) | C2—N1—C6—C5 | −2.0 (5) |
N6—Zn1—N1—C2 | −90.9 (2) | Zn1—N1—C6—C5 | 174.2 (3) |
N3—Zn1—N1—C2 | 178.1 (3) | C2—N1—C6—N2 | 179.4 (3) |
C8—N2—N3—C10 | 0.2 (3) | Zn1—N1—C6—N2 | −4.4 (4) |
C6—N2—N3—C10 | 176.0 (3) | C4—C5—C6—N1 | 0.8 (6) |
C8—N2—N3—Zn1 | −179.8 (2) | C4—C5—C6—N2 | 179.2 (3) |
C6—N2—N3—Zn1 | −4.1 (3) | C8—N2—C6—N1 | 180.0 (3) |
N1—Zn1—N3—C10 | −178.7 (4) | N3—N2—C6—N1 | 5.4 (4) |
N4—Zn1—N3—C10 | 1.5 (4) | C8—N2—C6—C5 | 1.5 (6) |
O3—Zn1—N3—C10 | −75.9 (4) | N3—N2—C6—C5 | −173.1 (3) |
O1—Zn1—N3—C10 | 179.5 (3) | N3—N2—C8—C9 | −0.3 (4) |
N6—Zn1—N3—C10 | 75.6 (4) | C6—N2—C8—C9 | −175.1 (3) |
N1—Zn1—N3—N2 | 1.4 (2) | N3—N2—C8—C7 | −177.8 (3) |
N4—Zn1—N3—N2 | −178.5 (2) | C6—N2—C8—C7 | 7.3 (6) |
O3—Zn1—N3—N2 | 104.2 (2) | N2—C8—C9—C10 | 0.2 (4) |
O1—Zn1—N3—N2 | −0.5 (4) | C7—C8—C9—C10 | 177.6 (4) |
N6—Zn1—N3—N2 | −104.3 (2) | N2—N3—C10—C9 | −0.1 (4) |
N1—Zn1—N4—C17 | −84 (2) | Zn1—N3—C10—C9 | −180.0 (3) |
O3—Zn1—N4—C17 | −177.9 (3) | N2—N3—C10—C11 | 179.4 (3) |
O1—Zn1—N4—C17 | −86.4 (3) | Zn1—N3—C10—C11 | −0.6 (6) |
N6—Zn1—N4—C17 | 2.4 (2) | C8—C9—C10—N3 | −0.1 (4) |
N3—Zn1—N4—C17 | 92.5 (3) | C8—C9—C10—C11 | −179.5 (4) |
N1—Zn1—N4—C13 | 88 (2) | Zn1—O3—C12—O4 | 177.0 (3) |
O3—Zn1—N4—C13 | −5.7 (2) | Zn1—O3—C12—C13 | −2.9 (4) |
O1—Zn1—N4—C13 | 85.7 (2) | C17—N4—C13—C14 | −0.8 (5) |
N6—Zn1—N4—C13 | 174.6 (2) | Zn1—N4—C13—C14 | −173.1 (2) |
N3—Zn1—N4—C13 | −95.3 (2) | C17—N4—C13—C12 | 178.3 (3) |
C19—N5—N6—C21 | −0.4 (4) | Zn1—N4—C13—C12 | 6.0 (3) |
C17—N5—N6—C21 | 178.3 (3) | O4—C12—C13—N4 | 178.1 (3) |
C19—N5—N6—Zn1 | 173.5 (2) | O3—C12—C13—N4 | −2.1 (4) |
C17—N5—N6—Zn1 | −7.7 (3) | O4—C12—C13—C14 | −2.9 (5) |
N1—Zn1—N6—C21 | −8.9 (4) | O3—C12—C13—C14 | 177.0 (3) |
N4—Zn1—N6—C21 | 173.9 (4) | N4—C13—C14—C15 | 1.6 (5) |
O3—Zn1—N6—C21 | 173.4 (4) | C12—C13—C14—C15 | −177.3 (3) |
O1—Zn1—N6—C21 | −85.5 (4) | C13—C14—C15—C16 | −0.8 (6) |
N3—Zn1—N6—C21 | 65.1 (4) | C14—C15—C16—C17 | −0.8 (6) |
N1—Zn1—N6—N5 | −179.8 (2) | C13—N4—C17—C16 | −0.9 (5) |
N4—Zn1—N6—N5 | 3.0 (2) | Zn1—N4—C17—C16 | 170.9 (3) |
O3—Zn1—N6—N5 | 2.4 (4) | C13—N4—C17—N5 | −179.0 (3) |
O1—Zn1—N6—N5 | 103.5 (2) | Zn1—N4—C17—N5 | −7.2 (4) |
N3—Zn1—N6—N5 | −105.9 (2) | C15—C16—C17—N4 | 1.7 (5) |
N1—Zn1—O1—C1 | 1.3 (3) | C15—C16—C17—N5 | 179.5 (3) |
N4—Zn1—O1—C1 | −178.8 (3) | C19—N5—C17—N4 | −172.0 (3) |
O3—Zn1—O1—C1 | −101.6 (3) | N6—N5—C17—N4 | 9.6 (4) |
N6—Zn1—O1—C1 | 107.9 (3) | C19—N5—C17—C16 | 10.0 (6) |
N3—Zn1—O1—C1 | 3.1 (5) | N6—N5—C17—C16 | −168.4 (3) |
N1—Zn1—O3—C12 | −172.6 (3) | N6—N5—C19—C20 | 0.1 (4) |
N4—Zn1—O3—C12 | 4.6 (3) | C17—N5—C19—C20 | −178.4 (4) |
O1—Zn1—O3—C12 | −95.5 (3) | N6—N5—C19—C18 | −178.3 (4) |
N6—Zn1—O3—C12 | 5.2 (4) | C17—N5—C19—C18 | 3.2 (7) |
N3—Zn1—O3—C12 | 113.9 (3) | N5—C19—C20—C21 | 0.3 (5) |
Zn1—O1—C1—O2 | −177.9 (4) | C18—C19—C20—C21 | 178.6 (4) |
Zn1—O1—C1—C2 | 0.3 (5) | N5—N6—C21—C20 | 0.6 (4) |
C6—N1—C2—C3 | 1.6 (5) | Zn1—N6—C21—C20 | −170.8 (3) |
Zn1—N1—C2—C3 | −174.9 (3) | N5—N6—C21—C22 | −177.8 (4) |
C6—N1—C2—C1 | −179.7 (3) | Zn1—N6—C21—C22 | 10.8 (7) |
Zn1—N1—C2—C1 | 3.8 (4) | C19—C20—C21—N6 | −0.6 (5) |
O1—C1—C2—N1 | −2.7 (5) | C19—C20—C21—C22 | 177.7 (4) |
Experimental details
Crystal data | |
Chemical formula | [Zn(C11H10N3O2)2]·3H2O |
Mr | 551.86 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 298 |
a, b, c (Å) | 9.8071 (9), 10.8388 (12), 12.6766 (16) |
α, β, γ (°) | 71.334 (2), 74.505 (2), 84.772 (3) |
V (Å3) | 1230.2 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.05 |
Crystal size (mm) | 0.50 × 0.48 × 0.34 |
Data collection | |
Diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.621, 0.716 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 6315, 4251, 3192 |
Rint | 0.021 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.042, 0.125, 1.04 |
No. of reflections | 4251 |
No. of parameters | 334 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.50, −0.38 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 1997a), SHELXL97 (Sheldrick, 1997a), SHELXTL (Sheldrick, 1997b).
Zn1—N1 | 2.077 (3) | Zn1—O1 | 2.122 (3) |
Zn1—N4 | 2.084 (3) | Zn1—N6 | 2.200 (3) |
Zn1—O3 | 2.109 (3) | Zn1—N3 | 2.219 (3) |
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In recent years, there has been an increasing interest in the coordination chemistry due to the increased recognition of it's role in catalysis enzymatic reactions, magnetism and molecular architectures (Costamagna et al., 1992; Bhatia et al., 1981). We report here the crystal structure of a new zinc(II) complex with the ligand 6- (3,5-dimethyl-1H-pyrazol-1-yl) picolinic acid(DPPA).(I) (Fig.1).
The title compound, (I), consists of a zinc(II) complex cation and three uncoordinated water molecules. In the cation(Fig. 1), the Co atom is six-coordinated by four N atoms and two O atoms from two DPPA ligands. The Zn(II) atom is a slightly distorted octahedral environment. The Zn—O bond length is 2.109 (3) and 2.122 (3) Å,The Zn—N distances range from 2.077 (3) to 2.219 (3) Å, i.e. normal values. The C1—C2 bond length is 1.528 (5) Å, being in the normal C—C ranges in cobaltcarboxylate complexes.The angles around Zn(II) atom are from 73.01 (10) to 177.31 (10)°. The DPPA molecule acts as a bidentate ligand.