Because of its versatile coordination modes and strong coordination ability, the mercaptoacetic acid substituted 1,2,4-triazole 2-{[5-(pyridin-2-yl)-4H-1,2,4-triazol-3-yl]sulfanyl}acetic acid (H2L) was synthesized and characterized. Treatment of H2L with cobalt and nickel acetate afforded the dinuclear complexes {μ-3-[(carboxylatomethyl)sulfanyl]-5-(pyridin-2-yl)-4H-1,2,4-triazol-4-ido-κ2N1,N5:N2,O}bis[aqua(methanol-κO)cobalt(II)] methanol disolvate, [Co2(C9H6N4O2S)2(CH3OH)2(H2O)2]·2CH3OH (1), and {μ-3-[(carboxylatomethyl)sulfanyl]-5-(pyridin-2-yl)-4H-1,2,4-triazol-4-ido-κ2N1,N5:N2,O}bis[diaquanickel(II)] methanol disolvate dihydrate, [Ni2(C9H6N4O2S)2(H2O)4]·2CH3OH·2H2O (2), respectively. Complex 1 crystallized in the monoclinic space group P21/c, while 2 crystallized in the tetragonal space group I41/a. Single-crystal X-ray diffraction studies revealed that H2L is doubly deprotonated and acts as a tetradentate bridging ligand in complexes 1 and 2. For both of the obtained complexes, extensive hydrogen-bond interactions contribute to the formation of their three-dimensional supermolecular structures. Hirshfeld surface analysis was used to illustrate the intermolecular interactions. Additionally, the urease inhibitory activities of 1, 2 and H2L were investigated against jack bean urease, where the two complexes revealed strong urease inhibition activities.
Supporting information
CCDC references: 1966374; 1966373
For both structures, data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015). Program(s) used to solve structure: SUPERFLIP (Palatinus & Chapuis, 2007) for (1); SHELXS97 (Sheldrick, 2008) for (2). For both structures, program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009).
{µ-3-[(Carboxylatomethyl)sulfanyl]-5-(pyridin-2-yl)-4
H-1,2,4-triazol-4-ido-
κ2N1,
N5:
N2,
O}bis[aqua(methanol-
κO)cobalt(II)] methanol disolvate (1)
top
Crystal data top
[Co2(C9H6N4O2S)2(CH4O)2(H2O)2]·2CH4O | F(000) = 772 |
Mr = 375.27 | Dx = 1.681 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 9.5941 (5) Å | Cell parameters from 3192 reflections |
b = 14.9735 (5) Å | θ = 3.5–27.9° |
c = 10.7212 (5) Å | µ = 1.33 mm−1 |
β = 105.719 (5)° | T = 293 K |
V = 1482.58 (11) Å3 | Block, clear light red |
Z = 4 | 0.13 × 0.1 × 0.06 mm |
Data collection top
Rigaku OD SuperNova Dual source diffractometer with an Eos detector | 2813 independent reflections |
Radiation source: micro-focus sealed X-ray tube, SuperNova (Mo) X-ray Source | 2198 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.040 |
Detector resolution: 16.0793 pixels mm-1 | θmax = 25.7°, θmin = 3.4° |
ω scans | h = −11→11 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | k = −18→18 |
Tmin = 0.697, Tmax = 1.000 | l = −13→13 |
9634 measured reflections | |
Refinement top
Refinement on F2 | Primary atom site location: iterative |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.100 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | w = 1/[σ2(Fo2) + (0.0452P)2 + 0.6443P] where P = (Fo2 + 2Fc2)/3 |
2813 reflections | (Δ/σ)max = 0.002 |
205 parameters | Δρmax = 0.39 e Å−3 |
0 restraints | Δρmin = −0.38 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds 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 > 2sigma(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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
O5 | 0.0600 (3) | 0.74701 (16) | 0.0046 (3) | 0.0537 (7) | |
H5 | −0.0110 | 0.7161 | 0.0029 | 0.081* | |
Co1 | 0.43485 (5) | 0.58198 (2) | 0.12944 (4) | 0.03065 (15) | |
C1 | 0.1824 (4) | 0.6061 (2) | 0.2688 (3) | 0.0424 (8) | |
H1 | 0.2315 | 0.6572 | 0.3057 | 0.051* | |
C2 | 0.0517 (4) | 0.5871 (2) | 0.2921 (3) | 0.0498 (9) | |
H2 | 0.0128 | 0.6253 | 0.3422 | 0.060* | |
C3 | −0.0206 (4) | 0.5109 (2) | 0.2404 (4) | 0.0507 (9) | |
H3 | −0.1093 | 0.4968 | 0.2549 | 0.061* | |
C4 | 0.0402 (4) | 0.4552 (2) | 0.1663 (3) | 0.0411 (8) | |
H4 | −0.0056 | 0.4025 | 0.1318 | 0.049* | |
C5 | 0.1700 (3) | 0.47971 (18) | 0.1449 (3) | 0.0313 (7) | |
C6 | 0.2399 (3) | 0.42889 (18) | 0.0612 (3) | 0.0296 (7) | |
C7 | 0.2879 (3) | 0.33642 (19) | −0.0663 (3) | 0.0337 (7) | |
C8 | 0.4398 (4) | 0.1962 (2) | −0.1377 (4) | 0.0473 (9) | |
H8A | 0.4916 | 0.2105 | −0.0490 | 0.057* | |
H8B | 0.4290 | 0.1318 | −0.1435 | 0.057* | |
C9 | 0.5307 (4) | 0.22571 (19) | −0.2260 (3) | 0.0353 (7) | |
C10 | 0.6575 (5) | 0.5355 (3) | 0.4020 (4) | 0.0698 (12) | |
H10A | 0.7565 | 0.5221 | 0.4060 | 0.105* | |
H10B | 0.6311 | 0.5057 | 0.4714 | 0.105* | |
H10C | 0.6466 | 0.5988 | 0.4099 | 0.105* | |
C11 | 0.0690 (5) | 0.8148 (3) | 0.0918 (5) | 0.0807 (14) | |
H11A | 0.1567 | 0.8479 | 0.0994 | 0.121* | |
H11B | 0.0696 | 0.7904 | 0.1747 | 0.121* | |
H11C | −0.0127 | 0.8538 | 0.0625 | 0.121* | |
H3A | 0.589 (6) | 0.453 (4) | 0.271 (5) | 0.121* | |
N1 | 0.2425 (3) | 0.55455 (16) | 0.1956 (2) | 0.0340 (6) | |
N2 | 0.3592 (3) | 0.45912 (15) | 0.0357 (2) | 0.0307 (6) | |
N3 | 0.3906 (3) | 0.39900 (15) | −0.0502 (2) | 0.0316 (6) | |
N4 | 0.1911 (3) | 0.35183 (16) | 0.0016 (2) | 0.0359 (6) | |
O1 | 0.5363 (3) | 0.30680 (13) | −0.2522 (2) | 0.0415 (6) | |
O2 | 0.5970 (3) | 0.16538 (13) | −0.2667 (2) | 0.0474 (6) | |
O3 | 0.5676 (3) | 0.50635 (15) | 0.2832 (2) | 0.0520 (7) | |
O4 | 0.3017 (3) | 0.65918 (15) | −0.0206 (2) | 0.0486 (6) | |
H4A | 0.2302 | 0.6927 | −0.0197 | 0.073* | |
H4B | 0.3305 | 0.6545 | −0.0886 | 0.073* | |
S1 | 0.26298 (10) | 0.24579 (6) | −0.17317 (10) | 0.0563 (3) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
O5 | 0.0494 (17) | 0.0439 (14) | 0.0777 (18) | −0.0033 (11) | 0.0340 (15) | −0.0048 (13) |
Co1 | 0.0413 (3) | 0.0196 (2) | 0.0368 (3) | −0.00182 (17) | 0.0205 (2) | −0.00387 (16) |
C1 | 0.059 (2) | 0.0312 (16) | 0.045 (2) | −0.0015 (15) | 0.0283 (18) | −0.0091 (14) |
C2 | 0.063 (3) | 0.045 (2) | 0.051 (2) | 0.0070 (18) | 0.033 (2) | −0.0092 (16) |
C3 | 0.051 (2) | 0.054 (2) | 0.057 (2) | 0.0008 (18) | 0.0332 (19) | −0.0041 (18) |
C4 | 0.044 (2) | 0.0358 (17) | 0.0499 (19) | −0.0040 (15) | 0.0236 (17) | −0.0062 (15) |
C5 | 0.0378 (19) | 0.0261 (15) | 0.0346 (16) | 0.0011 (13) | 0.0174 (14) | 0.0009 (12) |
C6 | 0.0322 (18) | 0.0246 (14) | 0.0353 (16) | −0.0001 (12) | 0.0149 (14) | −0.0009 (12) |
C7 | 0.0339 (18) | 0.0262 (15) | 0.0460 (18) | −0.0019 (13) | 0.0195 (15) | −0.0080 (13) |
C8 | 0.073 (3) | 0.0228 (15) | 0.062 (2) | −0.0019 (15) | 0.045 (2) | −0.0035 (15) |
C9 | 0.052 (2) | 0.0238 (15) | 0.0368 (17) | −0.0052 (13) | 0.0228 (15) | −0.0057 (13) |
C10 | 0.083 (3) | 0.059 (3) | 0.061 (3) | 0.018 (2) | 0.009 (2) | −0.012 (2) |
C11 | 0.071 (3) | 0.076 (3) | 0.094 (4) | −0.019 (3) | 0.022 (3) | −0.006 (3) |
N1 | 0.0466 (17) | 0.0252 (12) | 0.0359 (14) | 0.0016 (11) | 0.0209 (13) | −0.0013 (11) |
N2 | 0.0373 (16) | 0.0227 (12) | 0.0366 (14) | 0.0004 (11) | 0.0177 (12) | −0.0051 (10) |
N3 | 0.0369 (16) | 0.0232 (12) | 0.0390 (14) | −0.0017 (10) | 0.0178 (12) | −0.0088 (10) |
N4 | 0.0412 (17) | 0.0273 (13) | 0.0454 (16) | −0.0024 (11) | 0.0225 (13) | −0.0053 (11) |
O1 | 0.0694 (16) | 0.0201 (10) | 0.0449 (13) | −0.0054 (10) | 0.0324 (12) | −0.0042 (9) |
O2 | 0.0729 (18) | 0.0242 (11) | 0.0614 (15) | 0.0004 (10) | 0.0460 (14) | −0.0041 (10) |
O3 | 0.0767 (19) | 0.0247 (11) | 0.0475 (15) | 0.0024 (12) | 0.0046 (13) | −0.0006 (10) |
O4 | 0.0547 (16) | 0.0550 (15) | 0.0461 (14) | 0.0216 (12) | 0.0308 (12) | 0.0130 (11) |
S1 | 0.0523 (6) | 0.0462 (5) | 0.0800 (7) | −0.0165 (4) | 0.0345 (6) | −0.0363 (5) |
Geometric parameters (Å, º) top
O5—H5 | 0.8200 | C7—N4 | 1.346 (4) |
O5—C11 | 1.367 (5) | C7—S1 | 1.750 (3) |
Co1—N1 | 2.187 (3) | C8—H8A | 0.9700 |
Co1—N2 | 2.127 (2) | C8—H8B | 0.9700 |
Co1—N3i | 2.093 (2) | C8—C9 | 1.517 (4) |
Co1—O1i | 2.094 (2) | C8—S1 | 1.796 (4) |
Co1—O3 | 2.118 (2) | C9—O1 | 1.251 (3) |
Co1—O4 | 2.108 (2) | C9—O2 | 1.249 (3) |
C1—H1 | 0.9300 | C10—H10A | 0.9600 |
C1—C2 | 1.373 (5) | C10—H10B | 0.9600 |
C1—N1 | 1.338 (4) | C10—H10C | 0.9600 |
C2—H2 | 0.9300 | C10—O3 | 1.400 (4) |
C2—C3 | 1.372 (5) | C11—H11A | 0.9600 |
C3—H3 | 0.9300 | C11—H11B | 0.9600 |
C3—C4 | 1.385 (4) | C11—H11C | 0.9600 |
C4—H4 | 0.9300 | N2—N3 | 1.379 (3) |
C4—C5 | 1.375 (4) | N3—Co1i | 2.093 (2) |
C5—C6 | 1.470 (4) | O1—Co1i | 2.094 (2) |
C5—N1 | 1.353 (4) | O3—H3A | 0.84 (6) |
C6—N2 | 1.326 (4) | O4—H4A | 0.8522 |
C6—N4 | 1.340 (4) | O4—H4B | 0.8499 |
C7—N3 | 1.336 (4) | | |
| | | |
C11—O5—H5 | 109.5 | C9—C8—H8A | 108.6 |
N2—Co1—N1 | 77.33 (9) | C9—C8—H8B | 108.6 |
N3i—Co1—N1 | 174.48 (9) | C9—C8—S1 | 114.6 (2) |
N3i—Co1—N2 | 97.73 (9) | S1—C8—H8A | 108.6 |
N3i—Co1—O1i | 99.37 (9) | S1—C8—H8B | 108.6 |
N3i—Co1—O3 | 90.55 (11) | O1—C9—C8 | 119.4 (3) |
N3i—Co1—O4 | 90.11 (9) | O2—C9—C8 | 116.1 (3) |
O1i—Co1—N1 | 85.71 (9) | O2—C9—O1 | 124.5 (3) |
O1i—Co1—N2 | 162.68 (9) | H10A—C10—H10B | 109.5 |
O1i—Co1—O3 | 89.24 (9) | H10A—C10—H10C | 109.5 |
O1i—Co1—O4 | 89.61 (9) | H10B—C10—H10C | 109.5 |
O3—Co1—N1 | 91.71 (10) | O3—C10—H10A | 109.5 |
O3—Co1—N2 | 87.80 (9) | O3—C10—H10B | 109.5 |
O4—Co1—N1 | 87.72 (9) | O3—C10—H10C | 109.5 |
O4—Co1—N2 | 93.16 (9) | O5—C11—H11A | 109.5 |
O4—Co1—O3 | 178.75 (9) | O5—C11—H11B | 109.5 |
C2—C1—H1 | 118.4 | O5—C11—H11C | 109.5 |
N1—C1—H1 | 118.4 | H11A—C11—H11B | 109.5 |
N1—C1—C2 | 123.2 (3) | H11A—C11—H11C | 109.5 |
C1—C2—H2 | 120.5 | H11B—C11—H11C | 109.5 |
C3—C2—C1 | 119.1 (3) | C1—N1—Co1 | 128.2 (2) |
C3—C2—H2 | 120.5 | C1—N1—C5 | 117.1 (3) |
C2—C3—H3 | 120.4 | C5—N1—Co1 | 114.39 (19) |
C2—C3—C4 | 119.1 (3) | C6—N2—Co1 | 113.67 (18) |
C4—C3—H3 | 120.4 | C6—N2—N3 | 105.8 (2) |
C3—C4—H4 | 120.8 | N3—N2—Co1 | 140.52 (19) |
C5—C4—C3 | 118.4 (3) | C7—N3—Co1i | 133.35 (19) |
C5—C4—H4 | 120.8 | C7—N3—N2 | 104.9 (2) |
C4—C5—C6 | 123.2 (3) | N2—N3—Co1i | 121.75 (18) |
N1—C5—C4 | 123.0 (3) | C6—N4—C7 | 101.7 (2) |
N1—C5—C6 | 113.8 (3) | C9—O1—Co1i | 129.6 (2) |
N2—C6—C5 | 120.7 (2) | Co1—O3—H3A | 120 (4) |
N2—C6—N4 | 113.9 (2) | C10—O3—Co1 | 129.3 (2) |
N4—C6—C5 | 125.4 (3) | C10—O3—H3A | 109 (4) |
N3—C7—N4 | 113.8 (3) | Co1—O4—H4A | 129.6 |
N3—C7—S1 | 126.4 (2) | Co1—O4—H4B | 109.8 |
N4—C7—S1 | 119.7 (2) | H4A—O4—H4B | 120.6 |
H8A—C8—H8B | 107.6 | C7—S1—C8 | 103.21 (16) |
| | | |
Co1—N2—N3—Co1i | 0.4 (4) | N3i—Co1—N1—C5 | 24.6 (11) |
Co1—N2—N3—C7 | −178.2 (2) | N3i—Co1—N2—C6 | −177.0 (2) |
C1—C2—C3—C4 | 0.1 (6) | N3i—Co1—N2—N3 | −0.3 (3) |
C2—C1—N1—Co1 | 172.1 (3) | N3i—Co1—O3—C10 | 86.8 (3) |
C2—C1—N1—C5 | −1.1 (5) | N3—C7—N4—C6 | 0.3 (4) |
C2—C3—C4—C5 | −1.4 (5) | N3—C7—S1—C8 | 51.0 (3) |
C3—C4—C5—C6 | −176.0 (3) | N4—C6—N2—Co1 | 179.5 (2) |
C3—C4—C5—N1 | 1.6 (5) | N4—C6—N2—N3 | 1.7 (3) |
C4—C5—C6—N2 | 174.7 (3) | N4—C7—N3—Co1i | −177.7 (2) |
C4—C5—C6—N4 | −3.4 (5) | N4—C7—N3—N2 | 0.7 (4) |
C4—C5—N1—Co1 | −174.5 (2) | N4—C7—S1—C8 | −134.6 (3) |
C4—C5—N1—C1 | −0.4 (5) | O1i—Co1—N1—C1 | 8.0 (3) |
C5—C6—N2—Co1 | 1.2 (4) | O1i—Co1—N1—C5 | −178.7 (2) |
C5—C6—N2—N3 | −176.6 (3) | O1i—Co1—N2—C6 | 12.4 (4) |
C5—C6—N4—C7 | 177.0 (3) | O1i—Co1—N2—N3 | −170.9 (3) |
C6—C5—N1—Co1 | 3.4 (3) | O1i—Co1—O3—C10 | −12.5 (3) |
C6—C5—N1—C1 | 177.5 (3) | O2—C9—O1—Co1i | −133.9 (3) |
C6—N2—N3—Co1i | 177.22 (19) | O3—Co1—N1—C1 | 97.1 (3) |
C6—N2—N3—C7 | −1.4 (3) | O3—Co1—N1—C5 | −89.5 (2) |
C8—C9—O1—Co1i | 45.3 (4) | O3—Co1—N2—C6 | 92.7 (2) |
C9—C8—S1—C7 | −95.7 (3) | O3—Co1—N2—N3 | −90.6 (3) |
N1—Co1—N2—C6 | 0.5 (2) | O4—Co1—N1—C1 | −81.8 (3) |
N1—Co1—N2—N3 | 177.1 (3) | O4—Co1—N1—C5 | 91.6 (2) |
N1—Co1—O3—C10 | −98.2 (3) | O4—Co1—N2—C6 | −86.5 (2) |
N1—C1—C2—C3 | 1.3 (6) | O4—Co1—N2—N3 | 90.2 (3) |
N1—C5—C6—N2 | −3.1 (4) | O4—Co1—O3—C10 | −35 (5) |
N1—C5—C6—N4 | 178.7 (3) | S1—C7—N3—Co1i | −3.0 (5) |
N2—Co1—N1—C1 | −175.5 (3) | S1—C7—N3—N2 | 175.5 (2) |
N2—Co1—N1—C5 | −2.2 (2) | S1—C7—N4—C6 | −174.8 (2) |
N2—Co1—O3—C10 | −175.5 (3) | S1—C8—C9—O1 | 45.2 (4) |
N2—C6—N4—C7 | −1.3 (3) | S1—C8—C9—O2 | −135.5 (3) |
N3i—Co1—N1—C1 | −148.8 (9) | | |
Symmetry code: (i) −x+1, −y+1, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O5—H5···N4ii | 0.82 | 1.99 | 2.813 (3) | 176 |
O3—H3A···O2iii | 0.84 (6) | 1.83 (6) | 2.657 (3) | 169 (5) |
O4—H4A···O5 | 0.85 | 1.90 | 2.742 (3) | 167 |
O4—H4B···O2iv | 0.85 | 1.87 | 2.711 (3) | 170 |
Symmetry codes: (ii) −x, −y+1, −z; (iii) x, −y+1/2, z+1/2; (iv) −x+1, y+1/2, −z−1/2. |
{µ-3-[(Carboxylatomethyl)sulfanyl]-5-(pyridin-2-yl)-4
H-1,2,4-triazol-4-ido-
κ2N1,
N5:
N2,
O}bis[diaquanickel(II)]
methanol disolvate dihydrate (2)
top
Crystal data top
[Ni2(C9H6N4O2S)2(H2O)4]·2CH4O·2H2O | Dx = 1.592 Mg m−3 |
Mr = 379.04 | Cu Kα radiation, λ = 1.54184 Å |
Tetragonal, I41/a | Cell parameters from 2774 reflections |
a = 25.9178 (6) Å | θ = 5.0–71.1° |
c = 9.4186 (3) Å | µ = 3.33 mm−1 |
V = 6326.8 (3) Å3 | T = 293 K |
Z = 16 | Needle, clear light blue |
F(000) = 3136 | 0.35 × 0.06 × 0.02 mm |
Data collection top
Rigaku OD SuperNova Dual source diffractometer with an Eos detector | 2998 independent reflections |
Radiation source: micro-focus sealed X-ray tube, SuperNova (Cu) X-ray Source | 2584 reflections with I > 2σ(I) |
Mirror monochromator | Rint = 0.017 |
Detector resolution: 16.0793 pixels mm-1 | θmax = 70.9°, θmin = 4.8° |
ω scans | h = −31→20 |
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015) | k = −31→19 |
Tmin = 0.708, Tmax = 1.000 | l = −5→11 |
6205 measured reflections | |
Refinement top
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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.086 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.034P)2 + 11.3278P] where P = (Fo2 + 2Fc2)/3 |
2998 reflections | (Δ/σ)max = 0.002 |
202 parameters | Δρmax = 0.50 e Å−3 |
0 restraints | Δρmin = −0.56 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds 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 > 2sigma(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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
C1 | 0.62621 (10) | 0.54575 (10) | 0.3750 (3) | 0.0452 (6) | |
H1 | 0.6450 | 0.5714 | 0.3293 | 0.054* | |
C2 | 0.63899 (11) | 0.53296 (12) | 0.5129 (3) | 0.0554 (7) | |
H2 | 0.6660 | 0.5498 | 0.5587 | 0.067* | |
C3 | 0.61159 (12) | 0.49538 (12) | 0.5815 (3) | 0.0562 (8) | |
H3 | 0.6197 | 0.4863 | 0.6744 | 0.067* | |
C4 | 0.57149 (10) | 0.47095 (10) | 0.5103 (3) | 0.0448 (6) | |
H4 | 0.5520 | 0.4455 | 0.5546 | 0.054* | |
C5 | 0.56117 (9) | 0.48542 (9) | 0.3718 (2) | 0.0327 (5) | |
C6 | 0.51970 (8) | 0.46248 (8) | 0.2875 (2) | 0.0309 (5) | |
C7 | 0.45898 (10) | 0.41799 (10) | 0.2127 (3) | 0.0426 (6) | |
C8 | 0.41489 (11) | 0.34246 (10) | 0.0452 (3) | 0.0521 (8) | |
H8A | 0.4492 | 0.3482 | 0.0070 | 0.063* | |
H8B | 0.4095 | 0.3055 | 0.0528 | 0.063* | |
C9 | 0.37550 (9) | 0.36507 (8) | −0.0535 (3) | 0.0332 (5) | |
C10 | 0.5565 (2) | 0.68384 (18) | 0.4412 (5) | 0.122 (2) | |
H10A | 0.5415 | 0.7041 | 0.5160 | 0.184* | |
H10B | 0.5546 | 0.7026 | 0.3535 | 0.184* | |
H10C | 0.5919 | 0.6766 | 0.4633 | 0.184* | |
N1 | 0.58785 (7) | 0.52255 (7) | 0.3046 (2) | 0.0335 (4) | |
N2 | 0.51009 (7) | 0.47989 (7) | 0.15716 (19) | 0.0284 (4) | |
N3 | 0.46936 (7) | 0.45106 (7) | 0.1073 (2) | 0.0324 (4) | |
N4 | 0.48905 (8) | 0.42343 (8) | 0.3277 (2) | 0.0413 (5) | |
Ni1 | 0.561554 (13) | 0.536693 (13) | 0.09288 (4) | 0.02623 (12) | |
O1 | 0.37598 (6) | 0.41291 (6) | −0.07627 (18) | 0.0345 (4) | |
O2 | 0.34293 (8) | 0.33542 (7) | −0.1045 (3) | 0.0664 (7) | |
O3 | 0.61271 (7) | 0.48027 (7) | 0.0287 (2) | 0.0536 (5) | |
H3A | 0.6057 | 0.4543 | −0.0231 | 0.080* | |
H3B | 0.6446 | 0.4859 | 0.0423 | 0.080* | |
O5 | 0.71385 (8) | 0.52417 (8) | 0.0399 (2) | 0.0603 (5) | |
H5A | 0.7372 | 0.5280 | 0.1026 | 0.090* | |
H5B | 0.6952 | 0.5510 | 0.0494 | 0.090* | |
O4 | 0.51684 (6) | 0.59610 (6) | 0.17180 (18) | 0.0397 (4) | |
H4A | 0.5221 | 0.6001 | 0.2602 | 0.059* | |
H4B | 0.4850 | 0.5895 | 0.1594 | 0.059* | |
O6 | 0.52968 (10) | 0.63812 (9) | 0.4282 (2) | 0.0635 (6) | |
H6 | 0.5263 | 0.6249 | 0.5067 | 0.095* | |
S1 | 0.41022 (4) | 0.37137 (4) | 0.21818 (8) | 0.0851 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
C1 | 0.0396 (13) | 0.0461 (14) | 0.0500 (15) | −0.0127 (11) | −0.0153 (12) | 0.0019 (12) |
C2 | 0.0498 (16) | 0.0610 (18) | 0.0555 (17) | −0.0166 (14) | −0.0255 (14) | 0.0003 (14) |
C3 | 0.0628 (18) | 0.0608 (18) | 0.0449 (15) | −0.0084 (15) | −0.0269 (14) | 0.0072 (13) |
C4 | 0.0498 (15) | 0.0415 (14) | 0.0430 (13) | −0.0062 (12) | −0.0147 (12) | 0.0074 (11) |
C5 | 0.0315 (11) | 0.0301 (11) | 0.0365 (12) | −0.0013 (9) | −0.0086 (9) | −0.0008 (9) |
C6 | 0.0309 (11) | 0.0295 (11) | 0.0324 (11) | −0.0036 (9) | −0.0043 (9) | −0.0003 (9) |
C7 | 0.0455 (14) | 0.0477 (14) | 0.0345 (12) | −0.0225 (12) | −0.0083 (11) | 0.0063 (11) |
C8 | 0.0553 (16) | 0.0328 (13) | 0.0683 (18) | −0.0147 (12) | −0.0342 (15) | 0.0124 (12) |
C9 | 0.0323 (11) | 0.0280 (11) | 0.0391 (12) | −0.0059 (9) | −0.0077 (10) | 0.0014 (9) |
C10 | 0.209 (6) | 0.084 (3) | 0.073 (3) | −0.056 (4) | −0.035 (3) | 0.011 (2) |
N1 | 0.0297 (9) | 0.0351 (10) | 0.0357 (10) | −0.0038 (8) | −0.0093 (8) | −0.0009 (8) |
N2 | 0.0261 (9) | 0.0292 (9) | 0.0299 (9) | −0.0061 (7) | −0.0049 (7) | −0.0015 (7) |
N3 | 0.0302 (9) | 0.0355 (10) | 0.0316 (9) | −0.0120 (8) | −0.0057 (8) | 0.0009 (8) |
N4 | 0.0462 (12) | 0.0433 (11) | 0.0344 (10) | −0.0170 (10) | −0.0099 (9) | 0.0058 (9) |
Ni1 | 0.02296 (19) | 0.02468 (19) | 0.0311 (2) | −0.00232 (14) | −0.00332 (15) | −0.00239 (14) |
O1 | 0.0269 (7) | 0.0258 (8) | 0.0507 (10) | −0.0037 (6) | −0.0054 (7) | 0.0020 (7) |
O2 | 0.0732 (14) | 0.0314 (9) | 0.0946 (16) | −0.0170 (9) | −0.0568 (13) | 0.0124 (10) |
O3 | 0.0312 (9) | 0.0390 (10) | 0.0906 (15) | 0.0013 (7) | −0.0007 (9) | −0.0284 (10) |
O5 | 0.0527 (12) | 0.0571 (12) | 0.0710 (14) | 0.0073 (10) | −0.0096 (10) | −0.0174 (11) |
O4 | 0.0311 (8) | 0.0423 (9) | 0.0456 (10) | 0.0054 (7) | −0.0064 (7) | −0.0137 (8) |
O6 | 0.0906 (16) | 0.0632 (13) | 0.0367 (10) | −0.0081 (12) | −0.0119 (11) | −0.0004 (9) |
S1 | 0.0997 (7) | 0.1112 (7) | 0.0445 (4) | −0.0825 (6) | −0.0237 (4) | 0.0248 (4) |
Geometric parameters (Å, º) top
C1—H1 | 0.9300 | C9—O2 | 1.238 (3) |
C1—C2 | 1.381 (4) | C10—H10A | 0.9600 |
C1—N1 | 1.338 (3) | C10—H10B | 0.9600 |
C2—H2 | 0.9300 | C10—H10C | 0.9600 |
C2—C3 | 1.368 (4) | C10—O6 | 1.379 (4) |
C3—H3 | 0.9300 | N1—Ni1 | 2.1386 (19) |
C3—C4 | 1.389 (4) | N2—N3 | 1.376 (2) |
C4—H4 | 0.9300 | N2—Ni1 | 2.0767 (17) |
C4—C5 | 1.383 (3) | N3—Ni1i | 2.0731 (18) |
C5—C6 | 1.463 (3) | Ni1—N3i | 2.0731 (18) |
C5—N1 | 1.344 (3) | Ni1—O1i | 2.0861 (15) |
C6—N2 | 1.331 (3) | Ni1—O3 | 2.0644 (17) |
C6—N4 | 1.341 (3) | Ni1—O4 | 2.0654 (16) |
C7—N3 | 1.339 (3) | O1—Ni1i | 2.0861 (15) |
C7—N4 | 1.342 (3) | O3—H3A | 0.8516 |
C7—S1 | 1.749 (2) | O3—H3B | 0.8492 |
C8—H8A | 0.9700 | O5—H5A | 0.8520 |
C8—H8B | 0.9700 | O5—H5B | 0.8508 |
C8—C9 | 1.500 (3) | O4—H4A | 0.8500 |
C8—S1 | 1.798 (3) | O4—H4B | 0.8505 |
C9—O1 | 1.258 (3) | O6—H6 | 0.8200 |
| | | |
C2—C1—H1 | 118.8 | C1—N1—C5 | 118.1 (2) |
N1—C1—H1 | 118.8 | C1—N1—Ni1 | 128.46 (17) |
N1—C1—C2 | 122.5 (3) | C5—N1—Ni1 | 113.47 (14) |
C1—C2—H2 | 120.3 | C6—N2—N3 | 105.91 (17) |
C3—C2—C1 | 119.4 (2) | C6—N2—Ni1 | 112.89 (14) |
C3—C2—H2 | 120.3 | N3—N2—Ni1 | 141.10 (14) |
C2—C3—H3 | 120.5 | C7—N3—N2 | 104.41 (17) |
C2—C3—C4 | 119.0 (3) | C7—N3—Ni1i | 134.00 (15) |
C4—C3—H3 | 120.5 | N2—N3—Ni1i | 121.59 (13) |
C3—C4—H4 | 120.8 | C6—N4—C7 | 101.27 (19) |
C5—C4—C3 | 118.4 (2) | N2—Ni1—N1 | 79.13 (7) |
C5—C4—H4 | 120.8 | N2—Ni1—O1i | 164.62 (7) |
C4—C5—C6 | 123.0 (2) | N3i—Ni1—N1 | 175.77 (7) |
N1—C5—C4 | 122.6 (2) | N3i—Ni1—N2 | 97.21 (7) |
N1—C5—C6 | 114.4 (2) | N3i—Ni1—O1i | 97.81 (7) |
N2—C6—C5 | 120.0 (2) | O1i—Ni1—N1 | 85.98 (7) |
N2—C6—N4 | 113.91 (19) | O3—Ni1—N1 | 86.97 (8) |
N4—C6—C5 | 126.1 (2) | O3—Ni1—N2 | 89.76 (7) |
N3—C7—N4 | 114.5 (2) | O3—Ni1—N3i | 95.17 (8) |
N3—C7—S1 | 127.55 (18) | O3—Ni1—O1i | 85.60 (7) |
N4—C7—S1 | 117.92 (18) | O3—Ni1—O4 | 173.61 (7) |
H8A—C8—H8B | 108.1 | O4—Ni1—N1 | 88.34 (7) |
C9—C8—H8A | 109.5 | O4—Ni1—N2 | 93.62 (7) |
C9—C8—H8B | 109.5 | O4—Ni1—N3i | 89.80 (7) |
C9—C8—S1 | 110.7 (2) | O4—Ni1—O1i | 89.75 (6) |
S1—C8—H8A | 109.5 | C9—O1—Ni1i | 129.61 (15) |
S1—C8—H8B | 109.5 | Ni1—O3—H3A | 126.3 |
O1—C9—C8 | 118.9 (2) | Ni1—O3—H3B | 117.3 |
O2—C9—C8 | 117.5 (2) | H3A—O3—H3B | 115.5 |
O2—C9—O1 | 123.5 (2) | H5A—O5—H5B | 103.6 |
H10A—C10—H10B | 109.5 | Ni1—O4—H4A | 110.8 |
H10A—C10—H10C | 109.5 | Ni1—O4—H4B | 110.3 |
H10B—C10—H10C | 109.5 | H4A—O4—H4B | 108.2 |
O6—C10—H10A | 109.5 | C10—O6—H6 | 109.5 |
O6—C10—H10B | 109.5 | C7—S1—C8 | 102.27 (13) |
O6—C10—H10C | 109.5 | | |
| | | |
C1—C2—C3—C4 | 0.0 (5) | C6—N2—Ni1—O1i | 12.2 (3) |
C1—N1—Ni1—N2 | −178.3 (2) | C6—N2—Ni1—O3 | 84.49 (16) |
C1—N1—Ni1—N3i | −148.2 (10) | C6—N2—Ni1—O4 | −90.08 (16) |
C1—N1—Ni1—O1i | 5.6 (2) | C8—C9—O1—Ni1i | 36.0 (3) |
C1—N1—Ni1—O3 | 91.4 (2) | C9—C8—S1—C7 | −98.1 (2) |
C1—N1—Ni1—O4 | −84.2 (2) | N1—C1—C2—C3 | −0.3 (5) |
C2—C1—N1—C5 | −0.1 (4) | N1—C5—C6—N2 | −2.1 (3) |
C2—C1—N1—Ni1 | 179.5 (2) | N1—C5—C6—N4 | 177.0 (2) |
C2—C3—C4—C5 | 0.6 (5) | N2—C6—N4—C7 | −0.6 (3) |
C3—C4—C5—C6 | −179.6 (2) | N3—C7—N4—C6 | −0.3 (3) |
C3—C4—C5—N1 | −1.0 (4) | N3—C7—S1—C8 | 45.0 (3) |
C4—C5—C6—N2 | 176.7 (2) | N3—N2—Ni1—N1 | −178.0 (2) |
C4—C5—C6—N4 | −4.3 (4) | N3—N2—Ni1—N3i | 4.1 (3) |
C4—C5—N1—C1 | 0.8 (4) | N3—N2—Ni1—O1i | −163.3 (2) |
C4—C5—N1—Ni1 | −179.0 (2) | N3—N2—Ni1—O3 | −91.0 (2) |
C5—C6—N2—N3 | −179.6 (2) | N3—N2—Ni1—O4 | 94.4 (2) |
C5—C6—N2—Ni1 | 3.3 (3) | N4—C6—N2—N3 | 1.2 (3) |
C5—C6—N4—C7 | −179.7 (2) | N4—C6—N2—Ni1 | −175.88 (16) |
C5—N1—Ni1—N2 | 1.43 (16) | N4—C7—N3—N2 | 1.0 (3) |
C5—N1—Ni1—N3i | 31.5 (11) | N4—C7—N3—Ni1i | −179.86 (18) |
C5—N1—Ni1—O1i | −174.69 (16) | N4—C7—S1—C8 | −137.5 (2) |
C5—N1—Ni1—O3 | −88.90 (16) | Ni1—N2—N3—C7 | 174.5 (2) |
C5—N1—Ni1—O4 | 95.44 (16) | Ni1—N2—N3—Ni1i | −4.8 (3) |
C6—C5—N1—C1 | 179.5 (2) | O2—C9—O1—Ni1i | −146.6 (2) |
C6—C5—N1—Ni1 | −0.2 (2) | S1—C7—N3—N2 | 178.5 (2) |
C6—N2—N3—C7 | −1.2 (2) | S1—C7—N3—Ni1i | −2.3 (4) |
C6—N2—N3—Ni1i | 179.46 (15) | S1—C7—N4—C6 | −178.08 (19) |
C6—N2—Ni1—N1 | −2.47 (15) | S1—C8—C9—O1 | 58.6 (3) |
C6—N2—Ni1—N3i | 179.67 (15) | S1—C8—C9—O2 | −118.9 (2) |
Symmetry code: (i) −x+1, −y+1, −z. |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3A···O2ii | 0.85 | 1.76 | 2.606 (3) | 171 |
O3—H3B···O5 | 0.85 | 2.05 | 2.860 (3) | 159 |
O5—H5A···O5iii | 0.85 | 2.02 | 2.8434 (16) | 163 |
O5—H5B···O1i | 0.85 | 2.08 | 2.863 (3) | 152 |
O4—H4A···O6 | 0.85 | 1.87 | 2.670 (3) | 155 |
O4—H4B···O2iv | 0.85 | 1.83 | 2.663 (2) | 165 |
O6—H6···N4v | 0.82 | 2.04 | 2.840 (3) | 165 |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) y+1/4, −x+3/4, −z−1/4; (iii) y+1/4, −x+5/4, z+1/4; (iv) −y+3/4, x+1/4, z+1/4; (v) −x+1, −y+1, −z+1. |
Inhibition of jack bean urease by H2L, 1 and 2. topCompound | IC50 (µM) | Compound | IC50 (µM) |
1 | 3.5±0.9 | H2L | 14.7±1.4 |
2 | 1.3±0.7 | AHA | 7.8±1.6 |
Each data represents mean±SD (n = 3) |