Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053681103128X/hb6336sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053681103128X/hb6336Isup2.hkl |
CCDC reference: 818241
Key indicators
- Single-crystal X-ray study
- T = 296 K
- Mean (C-C) = 0.004 Å
- R factor = 0.041
- wR factor = 0.104
- Data-to-parameter ratio = 15.9
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C26 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C29 PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of . 32 A 3 PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) ..... 4 PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 35 PLAT912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 6
Alert level G PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF .... ? PLAT154_ALERT_1_G The su's on the Cell Angles are Equal .......... 0.00100 Deg. PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 3 N4 -NI1 -N4 -C1 2.00 0.00 2.656 1.555 1.555 1.555 PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 8 N4 -NI1 -N4 -C2 15.00 0.00 2.656 1.555 1.555 1.555 PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 11 N1 -NI1 -N1 -C11 9.00 0.00 2.656 1.555 1.555 1.555 PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 16 N1 -NI1 -N1 -C12 10.00 0.00 2.656 1.555 1.555 1.555 PLAT793_ALERT_4_G The Model has Chirality at C25 (Verify) .... R PLAT793_ALERT_4_G The Model has Chirality at C28 (Verify) .... R
0 ALERT level A = Most likely a serious problem - resolve or explain 0 ALERT level B = A potentially serious problem, consider carefully 6 ALERT level C = Check. Ensure it is not caused by an omission or oversight 8 ALERT level G = General information/check it is not something unexpected 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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 7 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
NiCl2.6H2O (0.024 g, 0.1 mmol) was dissolved in ethanol (10 ml), and diniconazole(0.063 g, 0.2 mmol) was dissolved in ethanol (10 ml). The NiCl2 solution was added to the diniconazole solution slowly under stirring. The mixture were filtered after stirring for 1 h. Green blocks of (I) were obtained by slow concentration of an ethanol solution. Anal. Calcd. For C60H68Cl10NiN12O4 (%) (Mr = 1434.48): C, 50.24; H, 4.78; N, 11.72. Found (%): C, 55.21; H, 4.80; N, 11.70.
All H atoms were included in calculated positions and refined as riding atoms, with C—H = 0.93–0.96 Å, O—H = 0.82 Å, with Uiso(H) = 1.5 Ueq(C) for methyl H atoms and 1.2 Ueq(C) for all other H atoms.
Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
[NiCl2(C15H17Cl2N3O)4] | Z = 1 |
Mr = 1434.47 | F(000) = 742 |
Triclinic, P1 | Dx = 1.379 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 8.7598 (6) Å | Cell parameters from 3863 reflections |
b = 13.7800 (9) Å | θ = 2.5–26.1° |
c = 15.1344 (10) Å | µ = 0.72 mm−1 |
α = 90.672 (1)° | T = 296 K |
β = 98.521 (1)° | Block, green |
γ = 106.743 (1)° | 0.25 × 0.22 × 0.21 mm |
V = 1727.3 (2) Å3 |
Bruker APEXII CCD diffractometer | 6383 independent reflections |
Radiation source: fine-focus sealed tube | 4766 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
ϕ and ω scans | θmax = 25.5°, θmin = 2.5° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2007) | h = −10→10 |
Tmin = 0.840, Tmax = 0.863 | k = −16→16 |
13440 measured reflections | l = −18→18 |
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.104 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0497P)2 + 0.4285P] where P = (Fo2 + 2Fc2)/3 |
6383 reflections | (Δ/σ)max = 0.001 |
402 parameters | Δρmax = 0.35 e Å−3 |
0 restraints | Δρmin = −0.42 e Å−3 |
[NiCl2(C15H17Cl2N3O)4] | γ = 106.743 (1)° |
Mr = 1434.47 | V = 1727.3 (2) Å3 |
Triclinic, P1 | Z = 1 |
a = 8.7598 (6) Å | Mo Kα radiation |
b = 13.7800 (9) Å | µ = 0.72 mm−1 |
c = 15.1344 (10) Å | T = 296 K |
α = 90.672 (1)° | 0.25 × 0.22 × 0.21 mm |
β = 98.521 (1)° |
Bruker APEXII CCD diffractometer | 6383 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2007) | 4766 reflections with I > 2σ(I) |
Tmin = 0.840, Tmax = 0.863 | Rint = 0.025 |
13440 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.104 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.35 e Å−3 |
6383 reflections | Δρmin = −0.42 e Å−3 |
402 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 | ||
Ni1 | 0.5000 | 0.0000 | 0.5000 | 0.02802 (13) | |
Cl1 | 0.73567 (8) | −0.02454 (5) | 0.60068 (4) | 0.04154 (18) | |
Cl5 | 0.58239 (9) | −0.34451 (7) | 0.02533 (5) | 0.0630 (2) | |
Cl2 | 1.11706 (10) | 0.52902 (6) | 0.24982 (6) | 0.0638 (2) | |
Cl3 | 1.66829 (9) | 0.47117 (7) | 0.18141 (6) | 0.0634 (2) | |
Cl4 | 1.16064 (13) | −0.36651 (8) | −0.03016 (7) | 0.0854 (3) | |
N4 | 0.6518 (2) | 0.13360 (16) | 0.45770 (14) | 0.0341 (5) | |
N3 | 0.6487 (2) | −0.12645 (16) | 0.28494 (13) | 0.0332 (5) | |
N1 | 0.5419 (2) | −0.08273 (16) | 0.39414 (13) | 0.0347 (5) | |
N6 | 0.8613 (2) | 0.23450 (15) | 0.41014 (13) | 0.0316 (5) | |
C2 | 0.6135 (3) | 0.2041 (2) | 0.4058 (2) | 0.0512 (8) | |
H2 | 0.5084 | 0.2081 | 0.3926 | 0.061* | |
C12 | 0.4329 (3) | −0.1519 (2) | 0.33470 (19) | 0.0498 (8) | |
H12 | 0.3248 | −0.1765 | 0.3412 | 0.060* | |
C11 | 0.6754 (3) | −0.0703 (2) | 0.36072 (16) | 0.0351 (6) | |
H11 | 0.7757 | −0.0278 | 0.3866 | 0.042* | |
C20 | 0.7892 (3) | −0.3141 (2) | 0.06064 (17) | 0.0404 (7) | |
C16 | 1.0225 (3) | −0.2331 (2) | 0.16512 (18) | 0.0419 (7) | |
H16 | 1.0712 | −0.1945 | 0.2181 | 0.050* | |
N2 | 0.4896 (3) | −0.1819 (2) | 0.26754 (15) | 0.0504 (6) | |
C13 | 0.7614 (3) | −0.1355 (2) | 0.22698 (15) | 0.0317 (6) | |
C14 | 0.7522 (3) | −0.2281 (2) | 0.19829 (16) | 0.0374 (6) | |
H14 | 0.6722 | −0.2810 | 0.2164 | 0.045* | |
C15 | 0.8564 (3) | −0.25637 (19) | 0.14017 (16) | 0.0352 (6) | |
C19 | 0.8817 (4) | −0.3476 (2) | 0.00823 (19) | 0.0485 (7) | |
H19 | 0.8341 | −0.3863 | −0.0448 | 0.058* | |
C17 | 1.1169 (4) | −0.2659 (2) | 0.1134 (2) | 0.0478 (7) | |
H17 | 1.2281 | −0.2494 | 0.1311 | 0.057* | |
C18 | 1.0450 (4) | −0.3230 (2) | 0.0357 (2) | 0.0493 (8) | |
C1 | 0.8086 (3) | 0.15564 (19) | 0.45978 (16) | 0.0336 (6) | |
H1 | 0.8741 | 0.1211 | 0.4914 | 0.040* | |
C27 | 1.0189 (3) | 0.27541 (18) | 0.38578 (16) | 0.0298 (5) | |
C8 | 1.4775 (3) | 0.4233 (2) | 0.21011 (17) | 0.0405 (7) | |
C9 | 1.3818 (3) | 0.4858 (2) | 0.21392 (17) | 0.0421 (7) | |
H9 | 1.4153 | 0.5525 | 0.1973 | 0.051* | |
C5 | 1.1815 (3) | 0.3492 (2) | 0.26917 (16) | 0.0342 (6) | |
C7 | 1.4256 (3) | 0.3228 (2) | 0.23023 (18) | 0.0463 (7) | |
H7 | 1.4885 | 0.2798 | 0.2243 | 0.056* | |
C4 | 1.0282 (3) | 0.31053 (19) | 0.30519 (17) | 0.0355 (6) | |
H4 | 0.9329 | 0.3110 | 0.2690 | 0.043* | |
C6 | 1.2785 (3) | 0.2874 (2) | 0.25922 (18) | 0.0426 (7) | |
H6 | 1.2432 | 0.2197 | 0.2726 | 0.051* | |
N5 | 0.7347 (3) | 0.26722 (19) | 0.37477 (18) | 0.0533 (7) | |
C10 | 1.2342 (3) | 0.4480 (2) | 0.24291 (17) | 0.0380 (6) | |
C28 | 1.1612 (3) | 0.2793 (2) | 0.45744 (17) | 0.0352 (6) | |
H28 | 1.2570 | 0.2937 | 0.4280 | 0.042* | |
C25 | 0.8684 (3) | −0.0378 (2) | 0.19969 (16) | 0.0358 (6) | |
H25 | 0.9532 | −0.0544 | 0.1725 | 0.043* | |
C29 | 1.1960 (3) | 0.3618 (2) | 0.53325 (18) | 0.0428 (7) | |
C26 | 0.7828 (4) | 0.0188 (2) | 0.13069 (19) | 0.0500 (8) | |
O2 | 1.1449 (2) | 0.18368 (14) | 0.49624 (13) | 0.0449 (5) | |
H2A | 1.1757 | 0.1469 | 0.4644 | 0.067* | |
O1 | 0.9460 (2) | 0.03079 (14) | 0.27532 (12) | 0.0452 (5) | |
H1A | 1.0243 | 0.0149 | 0.3002 | 0.068* | |
C30 | 0.6677 (4) | 0.0650 (3) | 0.1709 (3) | 0.0728 (11) | |
H30A | 0.6340 | 0.1104 | 0.1300 | 0.109* | |
H30B | 0.7220 | 0.1019 | 0.2264 | 0.109* | |
H30C | 0.5750 | 0.0119 | 0.1816 | 0.109* | |
C31 | 0.9151 (5) | 0.1044 (3) | 0.0990 (3) | 0.0811 (12) | |
H31A | 0.8668 | 0.1393 | 0.0535 | 0.122* | |
H31B | 0.9895 | 0.0762 | 0.0749 | 0.122* | |
H31C | 0.9716 | 0.1513 | 0.1486 | 0.122* | |
C32 | 1.0688 (4) | 0.3386 (3) | 0.5958 (2) | 0.0628 (9) | |
H32A | 1.0568 | 0.2719 | 0.6171 | 0.094* | |
H32B | 0.9674 | 0.3418 | 0.5637 | 0.094* | |
H32C | 1.1027 | 0.3877 | 0.6457 | 0.094* | |
C33 | 1.3603 (4) | 0.3659 (3) | 0.5870 (2) | 0.0716 (10) | |
H33A | 1.3912 | 0.4200 | 0.6325 | 0.107* | |
H33B | 1.4397 | 0.3775 | 0.5478 | 0.107* | |
H33C | 1.3532 | 0.3026 | 0.6145 | 0.107* | |
C34 | 1.2064 (5) | 0.4639 (2) | 0.4925 (2) | 0.0731 (11) | |
H34A | 1.2360 | 0.5165 | 0.5394 | 0.110* | |
H34B | 1.1034 | 0.4617 | 0.4589 | 0.110* | |
H34C | 1.2863 | 0.4777 | 0.4536 | 0.110* | |
C35 | 0.6923 (5) | −0.0543 (3) | 0.0510 (2) | 0.0822 (12) | |
H35A | 0.6015 | −0.1035 | 0.0687 | 0.123* | |
H35B | 0.7633 | −0.0882 | 0.0307 | 0.123* | |
H35C | 0.6552 | −0.0171 | 0.0035 | 0.123* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.0224 (2) | 0.0333 (3) | 0.0295 (2) | 0.00732 (19) | 0.00932 (17) | 0.00260 (19) |
Cl1 | 0.0324 (3) | 0.0500 (4) | 0.0446 (4) | 0.0167 (3) | 0.0042 (3) | 0.0057 (3) |
Cl5 | 0.0451 (4) | 0.0772 (6) | 0.0583 (5) | 0.0079 (4) | 0.0038 (4) | −0.0208 (4) |
Cl2 | 0.0602 (5) | 0.0569 (5) | 0.0886 (6) | 0.0290 (4) | 0.0312 (4) | 0.0276 (4) |
Cl3 | 0.0354 (4) | 0.0843 (6) | 0.0651 (5) | 0.0013 (4) | 0.0242 (4) | −0.0009 (4) |
Cl4 | 0.0851 (7) | 0.0949 (8) | 0.0974 (7) | 0.0448 (6) | 0.0457 (6) | −0.0131 (6) |
N4 | 0.0270 (11) | 0.0379 (13) | 0.0384 (12) | 0.0075 (10) | 0.0125 (9) | 0.0064 (10) |
N3 | 0.0280 (11) | 0.0401 (13) | 0.0317 (11) | 0.0084 (10) | 0.0082 (9) | −0.0035 (9) |
N1 | 0.0302 (12) | 0.0422 (14) | 0.0333 (11) | 0.0115 (10) | 0.0088 (9) | 0.0007 (10) |
N6 | 0.0273 (11) | 0.0302 (12) | 0.0371 (11) | 0.0058 (9) | 0.0098 (9) | 0.0066 (9) |
C2 | 0.0283 (15) | 0.055 (2) | 0.075 (2) | 0.0145 (14) | 0.0176 (14) | 0.0283 (16) |
C12 | 0.0275 (15) | 0.066 (2) | 0.0526 (18) | 0.0065 (14) | 0.0116 (13) | −0.0127 (15) |
C11 | 0.0291 (14) | 0.0413 (16) | 0.0339 (14) | 0.0077 (12) | 0.0069 (11) | −0.0045 (11) |
C20 | 0.0421 (16) | 0.0396 (17) | 0.0404 (15) | 0.0102 (13) | 0.0129 (12) | −0.0014 (12) |
C16 | 0.0440 (16) | 0.0460 (17) | 0.0378 (15) | 0.0177 (14) | 0.0044 (12) | −0.0013 (12) |
N2 | 0.0315 (13) | 0.0666 (18) | 0.0470 (14) | 0.0047 (12) | 0.0079 (11) | −0.0173 (12) |
C13 | 0.0296 (13) | 0.0413 (16) | 0.0248 (12) | 0.0118 (12) | 0.0038 (10) | −0.0022 (11) |
C14 | 0.0404 (15) | 0.0387 (16) | 0.0324 (14) | 0.0074 (12) | 0.0123 (11) | −0.0006 (12) |
C15 | 0.0451 (16) | 0.0315 (15) | 0.0326 (13) | 0.0129 (12) | 0.0142 (12) | 0.0010 (11) |
C19 | 0.061 (2) | 0.0440 (18) | 0.0421 (16) | 0.0139 (15) | 0.0161 (14) | −0.0082 (13) |
C17 | 0.0461 (17) | 0.0509 (19) | 0.0548 (18) | 0.0239 (15) | 0.0148 (14) | 0.0080 (15) |
C18 | 0.059 (2) | 0.0460 (19) | 0.0553 (19) | 0.0262 (16) | 0.0273 (16) | 0.0052 (15) |
C1 | 0.0273 (13) | 0.0353 (15) | 0.0366 (14) | 0.0048 (11) | 0.0084 (11) | 0.0070 (11) |
C27 | 0.0269 (13) | 0.0253 (14) | 0.0364 (13) | 0.0043 (10) | 0.0099 (10) | 0.0022 (10) |
C8 | 0.0294 (14) | 0.0551 (19) | 0.0337 (14) | 0.0043 (13) | 0.0105 (11) | 0.0009 (13) |
C9 | 0.0400 (16) | 0.0408 (17) | 0.0393 (15) | −0.0006 (13) | 0.0113 (12) | 0.0054 (12) |
C5 | 0.0304 (14) | 0.0399 (16) | 0.0308 (13) | 0.0060 (12) | 0.0089 (11) | 0.0051 (11) |
C7 | 0.0430 (17) | 0.058 (2) | 0.0441 (16) | 0.0196 (15) | 0.0153 (13) | 0.0031 (14) |
C4 | 0.0272 (13) | 0.0376 (16) | 0.0386 (14) | 0.0034 (11) | 0.0076 (11) | 0.0067 (12) |
C6 | 0.0459 (17) | 0.0371 (16) | 0.0450 (16) | 0.0088 (13) | 0.0146 (13) | 0.0082 (12) |
N5 | 0.0329 (13) | 0.0535 (16) | 0.0797 (18) | 0.0164 (12) | 0.0186 (12) | 0.0329 (14) |
C10 | 0.0364 (15) | 0.0428 (17) | 0.0353 (14) | 0.0111 (12) | 0.0085 (11) | 0.0072 (12) |
C28 | 0.0295 (13) | 0.0389 (16) | 0.0396 (14) | 0.0098 (12) | 0.0128 (11) | 0.0078 (12) |
C25 | 0.0342 (14) | 0.0384 (16) | 0.0368 (14) | 0.0118 (12) | 0.0097 (11) | −0.0013 (11) |
C29 | 0.0407 (16) | 0.0423 (17) | 0.0405 (15) | 0.0065 (13) | 0.0030 (12) | −0.0013 (13) |
C26 | 0.062 (2) | 0.0432 (18) | 0.0439 (16) | 0.0164 (15) | 0.0028 (14) | 0.0049 (13) |
O2 | 0.0480 (12) | 0.0463 (12) | 0.0510 (12) | 0.0247 (10) | 0.0186 (9) | 0.0152 (9) |
O1 | 0.0369 (11) | 0.0462 (12) | 0.0479 (11) | 0.0091 (9) | −0.0006 (9) | −0.0080 (9) |
C30 | 0.077 (3) | 0.068 (3) | 0.082 (3) | 0.041 (2) | 0.002 (2) | 0.014 (2) |
C31 | 0.102 (3) | 0.064 (2) | 0.078 (3) | 0.017 (2) | 0.026 (2) | 0.028 (2) |
C32 | 0.065 (2) | 0.074 (2) | 0.0489 (18) | 0.0181 (18) | 0.0136 (16) | −0.0163 (16) |
C33 | 0.049 (2) | 0.095 (3) | 0.056 (2) | 0.0064 (19) | −0.0071 (16) | −0.0044 (19) |
C34 | 0.095 (3) | 0.040 (2) | 0.072 (2) | 0.0069 (18) | 0.002 (2) | −0.0093 (17) |
C35 | 0.116 (3) | 0.071 (3) | 0.050 (2) | 0.029 (2) | −0.020 (2) | 0.0037 (18) |
Ni1—N1i | 2.091 (2) | C8—C7 | 1.380 (4) |
Ni1—N1 | 2.091 (2) | C9—C10 | 1.386 (4) |
Ni1—N4 | 2.106 (2) | C9—H9 | 0.9300 |
Ni1—N4i | 2.106 (2) | C5—C6 | 1.386 (4) |
Ni1—Cl1i | 2.4860 (6) | C5—C10 | 1.389 (4) |
Ni1—Cl1 | 2.4860 (6) | C5—C4 | 1.481 (3) |
Cl5—C20 | 1.736 (3) | C7—C6 | 1.378 (4) |
Cl2—C10 | 1.732 (3) | C7—H7 | 0.9300 |
Cl3—C8 | 1.733 (3) | C4—H4 | 0.9300 |
Cl4—C18 | 1.737 (3) | C6—H6 | 0.9300 |
N4—C1 | 1.314 (3) | C28—O2 | 1.426 (3) |
N4—C2 | 1.343 (3) | C28—C29 | 1.539 (4) |
N3—C11 | 1.328 (3) | C28—H28 | 0.9800 |
N3—N2 | 1.367 (3) | C25—O1 | 1.428 (3) |
N3—C13 | 1.444 (3) | C25—C26 | 1.545 (4) |
N1—C11 | 1.310 (3) | C25—H25 | 0.9800 |
N1—C12 | 1.353 (3) | C29—C34 | 1.527 (4) |
N6—C1 | 1.338 (3) | C29—C33 | 1.531 (4) |
N6—N5 | 1.355 (3) | C29—C32 | 1.534 (4) |
N6—C27 | 1.438 (3) | C26—C35 | 1.525 (4) |
C2—N5 | 1.315 (3) | C26—C30 | 1.528 (5) |
C2—H2 | 0.9300 | C26—C31 | 1.535 (4) |
C12—N2 | 1.307 (3) | O2—H2A | 0.8200 |
C12—H12 | 0.9300 | O1—H1A | 0.8200 |
C11—H11 | 0.9300 | C30—H30A | 0.9600 |
C20—C19 | 1.377 (4) | C30—H30B | 0.9600 |
C20—C15 | 1.387 (4) | C30—H30C | 0.9600 |
C16—C17 | 1.378 (4) | C31—H31A | 0.9600 |
C16—C15 | 1.389 (4) | C31—H31B | 0.9600 |
C16—H16 | 0.9300 | C31—H31C | 0.9600 |
C13—C14 | 1.319 (4) | C32—H32A | 0.9600 |
C13—C25 | 1.504 (4) | C32—H32B | 0.9600 |
C14—C15 | 1.481 (3) | C32—H32C | 0.9600 |
C14—H14 | 0.9300 | C33—H33A | 0.9600 |
C19—C18 | 1.370 (4) | C33—H33B | 0.9600 |
C19—H19 | 0.9300 | C33—H33C | 0.9600 |
C17—C18 | 1.368 (4) | C34—H34A | 0.9600 |
C17—H17 | 0.9300 | C34—H34B | 0.9600 |
C1—H1 | 0.9300 | C34—H34C | 0.9600 |
C27—C4 | 1.323 (3) | C35—H35A | 0.9600 |
C27—C28 | 1.514 (3) | C35—H35B | 0.9600 |
C8—C9 | 1.371 (4) | C35—H35C | 0.9600 |
N1i—Ni1—N1 | 180.0 | C6—C7—C8 | 118.7 (3) |
N1i—Ni1—N4 | 90.43 (8) | C6—C7—H7 | 120.7 |
N1—Ni1—N4 | 89.57 (8) | C8—C7—H7 | 120.7 |
N1i—Ni1—N4i | 89.57 (8) | C27—C4—C5 | 123.9 (2) |
N1—Ni1—N4i | 90.43 (8) | C27—C4—H4 | 118.1 |
N4—Ni1—N4i | 180.00 (9) | C5—C4—H4 | 118.1 |
N1i—Ni1—Cl1i | 91.80 (6) | C7—C6—C5 | 122.4 (3) |
N1—Ni1—Cl1i | 88.20 (6) | C7—C6—H6 | 118.8 |
N4—Ni1—Cl1i | 90.45 (6) | C5—C6—H6 | 118.8 |
N4i—Ni1—Cl1i | 89.55 (6) | C2—N5—N6 | 102.3 (2) |
N1i—Ni1—Cl1 | 88.20 (6) | C9—C10—C5 | 122.0 (3) |
N1—Ni1—Cl1 | 91.80 (6) | C9—C10—Cl2 | 118.2 (2) |
N4—Ni1—Cl1 | 89.55 (6) | C5—C10—Cl2 | 119.8 (2) |
N4i—Ni1—Cl1 | 90.45 (6) | O2—C28—C27 | 111.6 (2) |
Cl1i—Ni1—Cl1 | 180.000 (1) | O2—C28—C29 | 108.5 (2) |
C1—N4—C2 | 102.5 (2) | C27—C28—C29 | 115.3 (2) |
C1—N4—Ni1 | 126.49 (17) | O2—C28—H28 | 107.0 |
C2—N4—Ni1 | 129.53 (17) | C27—C28—H28 | 107.0 |
C11—N3—N2 | 109.2 (2) | C29—C28—H28 | 107.0 |
C11—N3—C13 | 129.2 (2) | O1—C25—C13 | 111.5 (2) |
N2—N3—C13 | 121.6 (2) | O1—C25—C26 | 108.0 (2) |
C11—N1—C12 | 102.3 (2) | C13—C25—C26 | 114.9 (2) |
C11—N1—Ni1 | 128.67 (17) | O1—C25—H25 | 107.4 |
C12—N1—Ni1 | 128.40 (17) | C13—C25—H25 | 107.4 |
C1—N6—N5 | 109.0 (2) | C26—C25—H25 | 107.4 |
C1—N6—C27 | 128.9 (2) | C34—C29—C33 | 109.3 (3) |
N5—N6—C27 | 121.71 (19) | C34—C29—C32 | 110.2 (3) |
N5—C2—N4 | 115.4 (2) | C33—C29—C32 | 109.0 (2) |
N5—C2—H2 | 122.3 | C34—C29—C28 | 109.1 (2) |
N4—C2—H2 | 122.3 | C33—C29—C28 | 106.4 (2) |
N2—C12—N1 | 115.6 (2) | C32—C29—C28 | 112.7 (2) |
N2—C12—H12 | 122.2 | C35—C26—C30 | 110.5 (3) |
N1—C12—H12 | 122.2 | C35—C26—C31 | 109.0 (3) |
N1—C11—N3 | 111.1 (2) | C30—C26—C31 | 108.9 (3) |
N1—C11—H11 | 124.5 | C35—C26—C25 | 109.1 (2) |
N3—C11—H11 | 124.5 | C30—C26—C25 | 112.3 (2) |
C19—C20—C15 | 122.1 (3) | C31—C26—C25 | 107.0 (3) |
C19—C20—Cl5 | 118.7 (2) | C28—O2—H2A | 109.5 |
C15—C20—Cl5 | 119.2 (2) | C25—O1—H1A | 109.5 |
C17—C16—C15 | 121.6 (3) | C26—C30—H30A | 109.5 |
C17—C16—H16 | 119.2 | C26—C30—H30B | 109.5 |
C15—C16—H16 | 119.2 | H30A—C30—H30B | 109.5 |
C12—N2—N3 | 101.9 (2) | C26—C30—H30C | 109.5 |
C14—C13—N3 | 116.9 (2) | H30A—C30—H30C | 109.5 |
C14—C13—C25 | 126.6 (2) | H30B—C30—H30C | 109.5 |
N3—C13—C25 | 116.4 (2) | C26—C31—H31A | 109.5 |
C13—C14—C15 | 126.6 (2) | C26—C31—H31B | 109.5 |
C13—C14—H14 | 116.7 | H31A—C31—H31B | 109.5 |
C15—C14—H14 | 116.7 | C26—C31—H31C | 109.5 |
C20—C15—C16 | 117.1 (2) | H31A—C31—H31C | 109.5 |
C20—C15—C14 | 120.6 (2) | H31B—C31—H31C | 109.5 |
C16—C15—C14 | 122.1 (2) | C29—C32—H32A | 109.5 |
C18—C19—C20 | 118.7 (3) | C29—C32—H32B | 109.5 |
C18—C19—H19 | 120.6 | H32A—C32—H32B | 109.5 |
C20—C19—H19 | 120.6 | C29—C32—H32C | 109.5 |
C18—C17—C16 | 119.1 (3) | H32A—C32—H32C | 109.5 |
C18—C17—H17 | 120.4 | H32B—C32—H32C | 109.5 |
C16—C17—H17 | 120.4 | C29—C33—H33A | 109.5 |
C17—C18—C19 | 121.4 (3) | C29—C33—H33B | 109.5 |
C17—C18—Cl4 | 120.1 (2) | H33A—C33—H33B | 109.5 |
C19—C18—Cl4 | 118.5 (2) | C29—C33—H33C | 109.5 |
N4—C1—N6 | 110.7 (2) | H33A—C33—H33C | 109.5 |
N4—C1—H1 | 124.6 | H33B—C33—H33C | 109.5 |
N6—C1—H1 | 124.6 | C29—C34—H34A | 109.5 |
C4—C27—N6 | 118.0 (2) | C29—C34—H34B | 109.5 |
C4—C27—C28 | 125.5 (2) | H34A—C34—H34B | 109.5 |
N6—C27—C28 | 116.37 (19) | C29—C34—H34C | 109.5 |
C9—C8—C7 | 121.1 (3) | H34A—C34—H34C | 109.5 |
C9—C8—Cl3 | 119.7 (2) | H34B—C34—H34C | 109.5 |
C7—C8—Cl3 | 119.2 (2) | C26—C35—H35A | 109.5 |
C8—C9—C10 | 118.9 (3) | C26—C35—H35B | 109.5 |
C8—C9—H9 | 120.6 | H35A—C35—H35B | 109.5 |
C10—C9—H9 | 120.6 | C26—C35—H35C | 109.5 |
C6—C5—C10 | 116.8 (2) | H35A—C35—H35C | 109.5 |
C6—C5—C4 | 121.2 (2) | H35B—C35—H35C | 109.5 |
C10—C5—C4 | 122.0 (2) | ||
N1i—Ni1—N4—C1 | 112.5 (2) | C20—C19—C18—C17 | −0.3 (5) |
N1—Ni1—N4—C1 | −67.5 (2) | C20—C19—C18—Cl4 | 179.4 (2) |
N4i—Ni1—N4—C1 | −17 (64) | C2—N4—C1—N6 | −1.0 (3) |
Cl1i—Ni1—N4—C1 | −155.7 (2) | Ni1—N4—C1—N6 | 166.02 (16) |
Cl1—Ni1—N4—C1 | 24.3 (2) | N5—N6—C1—N4 | 1.0 (3) |
N1i—Ni1—N4—C2 | −84.0 (3) | C27—N6—C1—N4 | −172.0 (2) |
N1—Ni1—N4—C2 | 96.0 (3) | C1—N6—C27—C4 | 143.7 (3) |
N4i—Ni1—N4—C2 | 146 (65) | N5—N6—C27—C4 | −28.5 (4) |
Cl1i—Ni1—N4—C2 | 7.8 (2) | C1—N6—C27—C28 | −39.4 (3) |
Cl1—Ni1—N4—C2 | −172.2 (2) | N5—N6—C27—C28 | 148.4 (2) |
N1i—Ni1—N1—C11 | −88 (100) | C7—C8—C9—C10 | 3.3 (4) |
N4—Ni1—N1—C11 | 37.1 (2) | Cl3—C8—C9—C10 | −175.63 (19) |
N4i—Ni1—N1—C11 | −142.9 (2) | C9—C8—C7—C6 | −3.6 (4) |
Cl1i—Ni1—N1—C11 | 127.5 (2) | Cl3—C8—C7—C6 | 175.4 (2) |
Cl1—Ni1—N1—C11 | −52.5 (2) | N6—C27—C4—C5 | −176.3 (2) |
N1i—Ni1—N1—C12 | 103 (100) | C28—C27—C4—C5 | 7.1 (4) |
N4—Ni1—N1—C12 | −131.9 (2) | C6—C5—C4—C27 | 60.4 (4) |
N4i—Ni1—N1—C12 | 48.1 (2) | C10—C5—C4—C27 | −120.3 (3) |
Cl1i—Ni1—N1—C12 | −41.4 (2) | C8—C7—C6—C5 | −0.2 (4) |
Cl1—Ni1—N1—C12 | 138.6 (2) | C10—C5—C6—C7 | 4.1 (4) |
C1—N4—C2—N5 | 0.8 (4) | C4—C5—C6—C7 | −176.6 (2) |
Ni1—N4—C2—N5 | −165.7 (2) | N4—C2—N5—N6 | −0.2 (4) |
C11—N1—C12—N2 | −0.5 (3) | C1—N6—N5—C2 | −0.4 (3) |
Ni1—N1—C12—N2 | 170.7 (2) | C27—N6—N5—C2 | 173.1 (2) |
C12—N1—C11—N3 | 1.3 (3) | C8—C9—C10—C5 | 0.8 (4) |
Ni1—N1—C11—N3 | −169.85 (16) | C8—C9—C10—Cl2 | 178.5 (2) |
N2—N3—C11—N1 | −1.7 (3) | C6—C5—C10—C9 | −4.4 (4) |
C13—N3—C11—N1 | −179.9 (2) | C4—C5—C10—C9 | 176.3 (2) |
N1—C12—N2—N3 | −0.5 (3) | C6—C5—C10—Cl2 | 178.0 (2) |
C11—N3—N2—C12 | 1.3 (3) | C4—C5—C10—Cl2 | −1.3 (3) |
C13—N3—N2—C12 | 179.6 (2) | C4—C27—C28—O2 | −132.6 (3) |
C11—N3—C13—C14 | 134.6 (3) | N6—C27—C28—O2 | 50.7 (3) |
N2—N3—C13—C14 | −43.4 (3) | C4—C27—C28—C29 | 103.0 (3) |
C11—N3—C13—C25 | −50.1 (3) | N6—C27—C28—C29 | −73.7 (3) |
N2—N3—C13—C25 | 131.9 (2) | C14—C13—C25—O1 | −135.0 (3) |
N3—C13—C14—C15 | −178.7 (2) | N3—C13—C25—O1 | 50.2 (3) |
C25—C13—C14—C15 | 6.6 (4) | C14—C13—C25—C26 | 101.7 (3) |
C19—C20—C15—C16 | 0.2 (4) | N3—C13—C25—C26 | −73.1 (3) |
Cl5—C20—C15—C16 | −179.4 (2) | O2—C28—C29—C34 | −177.5 (2) |
C19—C20—C15—C14 | −175.3 (3) | C27—C28—C29—C34 | −51.5 (3) |
Cl5—C20—C15—C14 | 5.1 (4) | O2—C28—C29—C33 | 64.7 (3) |
C17—C16—C15—C20 | −0.1 (4) | C27—C28—C29—C33 | −169.3 (2) |
C17—C16—C15—C14 | 175.4 (2) | O2—C28—C29—C32 | −54.8 (3) |
C13—C14—C15—C20 | −124.7 (3) | C27—C28—C29—C32 | 71.2 (3) |
C13—C14—C15—C16 | 60.0 (4) | O1—C25—C26—C35 | −177.4 (3) |
C15—C20—C19—C18 | −0.1 (4) | C13—C25—C26—C35 | −52.2 (3) |
Cl5—C20—C19—C18 | 179.5 (2) | O1—C25—C26—C30 | −54.5 (3) |
C15—C16—C17—C18 | −0.3 (4) | C13—C25—C26—C30 | 70.7 (3) |
C16—C17—C18—C19 | 0.4 (4) | O1—C25—C26—C31 | 64.9 (3) |
C16—C17—C18—Cl4 | −179.3 (2) | C13—C25—C26—C31 | −169.9 (3) |
Symmetry code: (i) −x+1, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···Cl1ii | 0.82 | 2.36 | 3.1460 (19) | 160 |
O2—H2A···Cl1ii | 0.82 | 2.32 | 3.123 (2) | 169 |
Symmetry code: (ii) −x+2, −y, −z+1. |
Experimental details
Crystal data | |
Chemical formula | [NiCl2(C15H17Cl2N3O)4] |
Mr | 1434.47 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 8.7598 (6), 13.7800 (9), 15.1344 (10) |
α, β, γ (°) | 90.672 (1), 98.521 (1), 106.743 (1) |
V (Å3) | 1727.3 (2) |
Z | 1 |
Radiation type | Mo Kα |
µ (mm−1) | 0.72 |
Crystal size (mm) | 0.25 × 0.22 × 0.21 |
Data collection | |
Diffractometer | Bruker APEXII CCD diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2007) |
Tmin, Tmax | 0.840, 0.863 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 13440, 6383, 4766 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.104, 1.02 |
No. of reflections | 6383 |
No. of parameters | 402 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.35, −0.42 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1A···Cl1i | 0.82 | 2.36 | 3.1460 (19) | 160 |
O2—H2A···Cl1i | 0.82 | 2.32 | 3.123 (2) | 169 |
Symmetry code: (i) −x+2, −y, −z+1. |
Diniconazole [(E)-(RS)-1-(2,4-dichlorophenyl)-4,4-dimethyl-2- (1H-1,2,4-triazol-1-yl)-pent-1-en-3-ol] is a highly active triazole fungicide (Sumitomo Chemical, 1984). It is widely used for control of a broad range of fungal diseases in many crops, such as corn, wheat, peanut, grape and apple (Huang et al., 2003; Zhou et al., 2008). Because of its strong antimicrobial activities and its wide applications, the synthesis of diniconazole (Fu et al., 2002; Xia et al., 2001) and its salts (Gao et al., 2001) have attracted much attention. Recently, our group have reported the crystal structure of diniconazole (Xiong et al., 2010). In this paper, we report the synthesis and crystal structure of a new nickel(II) complex, (I), incorporating diniconazole.
The asymmetric unit of the title compound, [Ni(C15H17Cl2N3O) 4Cl2], consists of one nickel(II) ion, two diniconazole ligands and one coordinated chloride ion. The Ni atom lies on an inversion center and has a slightly distorted octahedral geometry. The equatorial positions are occupied by four N atoms from four (E)-(RS)-1-(2,4- dichlorophenyl)-4,4-dimethyl-2-(1H-1,2,4-triazol-1-yl)-pent-1-en-3-ol ligands. The axial sites are occupied by two Cl atoms(Fig. 1). The Ni—N distance are 2.123 (3) and 2.147 (3) Å and Ni—Cl is 2.5222 (9) Å. In the crystal packing, intermolecular O—H···Cl hydrogen bonds (Table 1) link the molecules into chains along the a axis(Fig. 2). The structure of the title compound is isostructural to previously reported zinc (II) complexe constructed by Zn2+ and diniconazole (Gao et al., 2001).