Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680704384X/ng2321sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680704384X/ng2321Isup2.hkl |
CCDC reference: 663600
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.040
- wR factor = 0.063
- Data-to-parameter ratio = 12.7
checkCIF/PLATON results
No syntax errors found
Alert level C ABSTM02_ALERT_3_C The ratio of expected to reported Tmax/Tmin(RR') is < 0.90 Tmin and Tmax reported: 0.837 0.962 Tmin(prime) and Tmax expected: 0.914 0.932 RR(prime) = 0.887 Please check that your absorption correction is appropriate. PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low .... 42 Perc. PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT061_ALERT_3_C Tmax/Tmin Range Test RR' too Large ............. 0.88 PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.97 PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT230_ALERT_2_C Hirshfeld Test Diff for O1 - C1 .. 5.23 su PLAT230_ALERT_2_C Hirshfeld Test Diff for N2 - C18 .. 5.80 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C8 - C9 .. 5.42 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C13 - C14 .. 5.37 su PLAT230_ALERT_2_C Hirshfeld Test Diff for C16 - C17 .. 5.25 su PLAT417_ALERT_2_C Short Inter D-H..H-D H6A .. H8A .. 2.13 Ang. PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 26 O1 -NI1 -O4 -C11 -39.20 0.70 1.555 1.555 1.555 1.555 PLAT710_ALERT_4_C Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... # 34 O4 -NI1 -O1 -C1 42.80 0.70 1.555 1.555 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.83(3), Rep 0.829(10) ...... 3.00 su-Ra O3 -H3A 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.82(3), Rep 0.824(10) ...... 3.00 su-Ra O8 -H8A 1.555 1.555 PLAT731_ALERT_1_C Bond Calc 0.82(3), Rep 0.816(10) ...... 3.00 su-Ra O2 -H2A 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.83(3), Rep 0.829(10) ...... 3.00 su-Ra O3 -H3A 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.82(3), Rep 0.824(10) ...... 3.00 su-Ra O8 -H8A 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.82(3), Rep 0.816(10) ...... 3.00 su-Ra O2 -H2A 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 1.77(3), Rep 1.763(11) ...... 2.73 su-Ra H3A -O5 1.555 4.556 PLAT736_ALERT_1_C H...A Calc 1.80(3), Rep 1.795(11) ...... 2.73 su-Ra H8A -O1 1.555 6.657 PLAT736_ALERT_1_C H...A Calc 1.89(3), Rep 1.895(12) ...... 2.50 su-Ra H2A -O3 1.555 4.456 PLAT736_ALERT_1_C H...A Calc 1.94(3), Rep 1.936(12) ...... 2.50 su-Ra H6A -O8 1.555 6.557
Alert level G FORMU01_ALERT_1_G There is a discrepancy between the atom counts in the _chemical_formula_sum and _chemical_formula_moiety. This is usually due to the moiety formula being in the wrong format. Atom count from _chemical_formula_sum: C23 H32 N2 Ni1 O9 Atom count from _chemical_formula_moiety:C23 H32 N2 O9 PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature 293 K PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature . 293 K PLAT794_ALERT_5_G Check Predicted Bond Valency for Ni1 (2) 2.15 PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 7
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 24 ALERT level C = Check and explain 5 ALERT level G = General alerts; check 14 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 4 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion 1 ALERT type 5 Informative message, check
2-[tris(hydroxymethyl)methyliminomethyl]phenolate was synthesized using the salicylaldehyde and the 2-amino-2-(hydroxymethyl)propane-1,3-diol. A mixture of Nickel acetate dihydrate (0.11 g, 0.5 mmol), 2-[tris(hydroxymethyl)methyliminomethyl]phenolate (0.13 g, 0.5 mmol), and methanol (15 ml) was heated and stirring for 20 min. Suitable crystals were obtained by evaporation of the filtrate in air at room temperature.
All H atoms besides H atoms bonded to O—H were placed at calculated positions in the riding-model approximation (C—Haromatic = 0.93Å and C—Hmethyl = 0.96 Å), with their displacement parameters tied to those of the parent atoms by Uiso(H) = 1.2–1.5 times Ueq(C). H atoms bonded to O—H were located from different Fourier maps and were refined with restrained O—H distances with O—Hmethyl = 0.82 (1) Å.
Single-crystal X-ray diffraction analyses revealed that (I) is neutral, mononuclear molecule with the Ni(II) ion being octahedral coordination supplied by monoanionic and tridentate binding through the Ophen, Oalk and Nimi groups from two 2-[tris(hydroxymethyl)methyliminomethyl]phenolate ligands (Fig. 1). And The structure is isostructural with the zinc analog (Dey et al., 2002). Selected bond lengths and bond angels are listed in Table 1. Of the three –CH2OH groups, only one is bound to the nickel center, while the other two remain free. At the same time one methanol molecule is cocrystallized in this complex which makes abundant O—H···O hydrogen bonds (Table 2) between the molecules.
Mononuclear Cu(II) complex coordinatd by one chelate 2-[tris(hydroxymethyl)methyliminomethyl]phenolate was reported in crystal structure (Ni et al., 2005). And the isostructural zinc complex was reported by Dey et al. (2002).
See Dey et al. (2002) for the isostructural zinc analog. For a related CuII complex, see Ni (2005).
Data collection: COLLECT (Nonius, 1998); cell refinement: HKL SCALEPACK (Otwinowski & Minor, 1997); data reduction: HKL DENZO (Otwinowski & Minor, 1997) and maXus (Mackay et al., 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Sheldrick, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
Fig. 1. View of the local coordination of Ni(II) with the coordinated atoms numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. |
[Ni(C11H14NO4)2]·CH4O | Dx = 1.516 Mg m−3 |
Mr = 539.22 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 15150 reflections |
a = 11.1900 (3) Å | θ = 3.4–27.5° |
b = 18.8378 (5) Å | µ = 0.88 mm−1 |
c = 22.4202 (8) Å | T = 293 K |
V = 4726.1 (2) Å3 | Block, green |
Z = 8 | 0.1 × 0.08 × 0.08 mm |
F(000) = 2272 |
Nonius KappaCCD diffractometer | 4329 independent reflections |
Radiation source: fine-focus sealed tube | 1833 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.093 |
Detector resolution: 0.76 pixels mm-1 | θmax = 25.4°, θmin = 3.5° |
CCD scans | h = −13→13 |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | k = −22→22 |
Tmin = 0.837, Tmax = 0.962 | l = −26→27 |
8161 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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.063 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.82 | w = 1/[σ2(Fo2) + (0.0165P)2] where P = (Fo2 + 2Fc2)/3 |
4329 reflections | (Δ/σ)max = 0.001 |
340 parameters | Δρmax = 0.38 e Å−3 |
7 restraints | Δρmin = −0.26 e Å−3 |
[Ni(C11H14NO4)2]·CH4O | V = 4726.1 (2) Å3 |
Mr = 539.22 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 11.1900 (3) Å | µ = 0.88 mm−1 |
b = 18.8378 (5) Å | T = 293 K |
c = 22.4202 (8) Å | 0.1 × 0.08 × 0.08 mm |
Nonius KappaCCD diffractometer | 4329 independent reflections |
Absorption correction: multi-scan (SORTAV; Blessing, 1995) | 1833 reflections with I > 2σ(I) |
Tmin = 0.837, Tmax = 0.962 | Rint = 0.093 |
8161 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 7 restraints |
wR(F2) = 0.063 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.82 | Δρmax = 0.38 e Å−3 |
4329 reflections | Δρmin = −0.26 e Å−3 |
340 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 | 0.49786 (4) | 0.214735 (17) | 0.619437 (17) | 0.02801 (13) | |
N1 | 0.5029 (3) | 0.22644 (12) | 0.53015 (10) | 0.0246 (6) | |
N2 | 0.5308 (2) | 0.20154 (12) | 0.70767 (11) | 0.0274 (8) | |
O7 | 0.6646 (2) | 0.15588 (12) | 0.61811 (12) | 0.0351 (6) | |
O4 | 0.5970 (2) | 0.31185 (12) | 0.61416 (12) | 0.0361 (6) | |
O1 | 0.39482 (19) | 0.12901 (9) | 0.61149 (10) | 0.0325 (6) | |
O5 | 0.35296 (18) | 0.27329 (10) | 0.63661 (10) | 0.0338 (6) | |
O3 | 0.6982 (2) | 0.23657 (13) | 0.44870 (11) | 0.0442 (7) | |
H3A | 0.744 (3) | 0.2362 (17) | 0.4198 (11) | 0.066* | |
O8 | 0.7673 (3) | 0.10518 (13) | 0.79279 (10) | 0.0448 (7) | |
H8A | 0.804 (3) | 0.1107 (17) | 0.8242 (9) | 0.067* | |
O2 | 0.3458 (2) | 0.31959 (12) | 0.46821 (11) | 0.0396 (7) | |
H2A | 0.301 (3) | 0.2989 (16) | 0.4912 (13) | 0.059* | |
O6 | 0.4756 (2) | 0.06072 (12) | 0.76045 (12) | 0.0472 (7) | |
H6A | 0.4104 (17) | 0.0748 (18) | 0.7484 (17) | 0.071* | |
O9 | 0.5291 (3) | 0.45139 (14) | 0.64657 (12) | 0.0842 (10) | |
H9 | 0.518 (5) | 0.468 (2) | 0.6799 (9) | 0.126* | |
C23 | 0.5141 (4) | 0.50424 (18) | 0.60590 (17) | 0.0995 (18) | |
H23A | 0.5393 | 0.5485 | 0.6229 | 0.149* | |
H23B | 0.4314 | 0.5072 | 0.5949 | 0.149* | |
H23C | 0.5612 | 0.4942 | 0.5711 | 0.149* | |
C1 | 0.3786 (3) | 0.09038 (17) | 0.56388 (16) | 0.0277 (9) | |
C17 | 0.4001 (3) | 0.30043 (17) | 0.73773 (17) | 0.0341 (10) | |
C11 | 0.6375 (3) | 0.32327 (15) | 0.55423 (16) | 0.0355 (10) | |
H11A | 0.7138 | 0.2997 | 0.5488 | 0.043* | |
H11B | 0.6495 | 0.3737 | 0.5479 | 0.043* | |
C19 | 0.6216 (3) | 0.14735 (16) | 0.72315 (15) | 0.0258 (9) | |
C16 | 0.3750 (4) | 0.34180 (18) | 0.78839 (17) | 0.0491 (12) | |
H16A | 0.4181 | 0.3335 | 0.8232 | 0.059* | |
C10 | 0.6118 (3) | 0.29154 (16) | 0.44774 (15) | 0.0378 (10) | |
H10A | 0.5540 | 0.2825 | 0.4164 | 0.045* | |
H10B | 0.6504 | 0.3366 | 0.4395 | 0.045* | |
C22 | 0.6750 (3) | 0.15574 (16) | 0.78512 (14) | 0.0343 (10) | |
H22A | 0.7069 | 0.2033 | 0.7898 | 0.041* | |
H22B | 0.6136 | 0.1486 | 0.8151 | 0.041* | |
C8 | 0.5485 (3) | 0.29521 (17) | 0.50759 (15) | 0.0278 (9) | |
C18 | 0.4887 (3) | 0.24383 (16) | 0.74729 (15) | 0.0367 (9) | |
H18A | 0.5170 | 0.2381 | 0.7860 | 0.044* | |
C6 | 0.4161 (3) | 0.11161 (17) | 0.50603 (16) | 0.0265 (9) | |
C5 | 0.3961 (3) | 0.06634 (18) | 0.45729 (15) | 0.0384 (10) | |
H5A | 0.4206 | 0.0809 | 0.4196 | 0.046* | |
C7 | 0.4713 (3) | 0.17885 (17) | 0.49257 (15) | 0.0288 (10) | |
H7A | 0.4853 | 0.1887 | 0.4525 | 0.035* | |
C21 | 0.7194 (3) | 0.15597 (16) | 0.67598 (15) | 0.0347 (10) | |
H21A | 0.7619 | 0.2002 | 0.6823 | 0.042* | |
H21B | 0.7762 | 0.1172 | 0.6790 | 0.042* | |
C9 | 0.4411 (3) | 0.34640 (16) | 0.50372 (15) | 0.0356 (10) | |
H9A | 0.4116 | 0.3556 | 0.5437 | 0.043* | |
H9B | 0.4679 | 0.3912 | 0.4871 | 0.043* | |
C2 | 0.3211 (3) | 0.02409 (17) | 0.56840 (17) | 0.0428 (11) | |
H2B | 0.2943 | 0.0088 | 0.6055 | 0.051* | |
C12 | 0.3370 (3) | 0.31122 (17) | 0.68496 (18) | 0.0314 (10) | |
C20 | 0.5663 (3) | 0.07282 (15) | 0.71672 (15) | 0.0342 (10) | |
H20A | 0.5320 | 0.0679 | 0.6772 | 0.041* | |
H20B | 0.6284 | 0.0373 | 0.7210 | 0.041* | |
C15 | 0.2898 (4) | 0.39380 (18) | 0.78853 (19) | 0.0588 (14) | |
H15A | 0.2742 | 0.4209 | 0.8223 | 0.071* | |
C4 | 0.3417 (3) | 0.00142 (19) | 0.4632 (2) | 0.0502 (12) | |
H4A | 0.3307 | −0.0282 | 0.4305 | 0.060* | |
C13 | 0.2489 (3) | 0.36394 (17) | 0.68445 (16) | 0.0445 (11) | |
H13A | 0.2049 | 0.3720 | 0.6499 | 0.053* | |
C14 | 0.2268 (4) | 0.40409 (19) | 0.73480 (19) | 0.0565 (14) | |
H14A | 0.1684 | 0.4391 | 0.7332 | 0.068* | |
C3 | 0.3036 (4) | −0.01862 (18) | 0.5195 (2) | 0.0521 (13) | |
H3B | 0.2652 | −0.0620 | 0.5243 | 0.063* | |
H4B | 0.569 (3) | 0.3489 (10) | 0.6263 (14) | 0.071 (16)* | |
H7B | 0.716 (2) | 0.1614 (16) | 0.5924 (11) | 0.045 (14)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ni1 | 0.0288 (3) | 0.0313 (2) | 0.0239 (2) | −0.0010 (2) | −0.0014 (3) | −0.0011 (2) |
N1 | 0.0221 (17) | 0.0259 (15) | 0.0259 (17) | 0.0003 (16) | 0.0001 (18) | −0.0009 (13) |
N2 | 0.031 (2) | 0.0269 (16) | 0.0246 (18) | 0.0002 (14) | −0.0028 (15) | −0.0053 (13) |
O7 | 0.0325 (18) | 0.0504 (15) | 0.0224 (17) | 0.0055 (13) | 0.0036 (18) | −0.0002 (15) |
O4 | 0.0416 (18) | 0.0339 (15) | 0.0328 (18) | −0.0023 (13) | 0.0017 (16) | −0.0025 (15) |
O1 | 0.0404 (17) | 0.0362 (13) | 0.0208 (15) | −0.0126 (12) | 0.0043 (14) | −0.0043 (12) |
O5 | 0.0295 (16) | 0.0443 (14) | 0.0276 (16) | 0.0064 (12) | −0.0036 (13) | −0.0039 (13) |
O3 | 0.036 (2) | 0.0597 (16) | 0.0369 (19) | 0.0100 (15) | 0.0150 (14) | 0.0038 (15) |
O8 | 0.043 (2) | 0.0577 (15) | 0.0336 (18) | 0.0132 (14) | −0.0168 (15) | −0.0025 (15) |
O2 | 0.033 (2) | 0.0495 (17) | 0.036 (2) | −0.0014 (14) | −0.0043 (15) | 0.0075 (13) |
O6 | 0.046 (2) | 0.0514 (15) | 0.0442 (18) | −0.0093 (15) | −0.0015 (18) | 0.0109 (13) |
O9 | 0.131 (3) | 0.0654 (19) | 0.056 (2) | 0.0266 (19) | 0.016 (3) | −0.0011 (16) |
C23 | 0.156 (5) | 0.073 (3) | 0.069 (4) | 0.020 (4) | −0.012 (4) | −0.004 (2) |
C1 | 0.017 (2) | 0.031 (2) | 0.035 (3) | 0.0017 (19) | 0.001 (2) | 0.002 (2) |
C17 | 0.034 (3) | 0.035 (2) | 0.033 (3) | 0.005 (2) | 0.000 (2) | −0.011 (2) |
C11 | 0.035 (3) | 0.033 (2) | 0.039 (3) | −0.0045 (19) | 0.005 (2) | 0.0059 (19) |
C19 | 0.025 (3) | 0.031 (2) | 0.021 (2) | −0.0009 (19) | −0.002 (2) | −0.0037 (18) |
C16 | 0.057 (3) | 0.043 (2) | 0.047 (3) | −0.001 (2) | −0.005 (2) | −0.006 (2) |
C10 | 0.036 (3) | 0.044 (2) | 0.033 (3) | −0.006 (2) | 0.003 (2) | 0.008 (2) |
C22 | 0.035 (3) | 0.039 (2) | 0.029 (3) | −0.001 (2) | −0.006 (2) | 0.0011 (19) |
C8 | 0.024 (2) | 0.033 (2) | 0.026 (2) | 0.0019 (19) | −0.0035 (19) | 0.0041 (19) |
C18 | 0.044 (3) | 0.039 (2) | 0.026 (2) | −0.004 (2) | −0.007 (3) | 0.0013 (18) |
C6 | 0.026 (3) | 0.029 (2) | 0.025 (2) | 0.0015 (18) | −0.005 (2) | −0.0056 (19) |
C5 | 0.039 (3) | 0.043 (2) | 0.034 (3) | 0.000 (2) | 0.000 (2) | −0.001 (2) |
C7 | 0.025 (3) | 0.040 (2) | 0.022 (2) | 0.0035 (18) | 0.0014 (19) | 0.0043 (18) |
C21 | 0.033 (3) | 0.045 (2) | 0.026 (3) | 0.000 (2) | −0.007 (2) | 0.001 (2) |
C9 | 0.037 (3) | 0.036 (2) | 0.034 (3) | −0.007 (2) | −0.002 (2) | 0.004 (2) |
C2 | 0.050 (3) | 0.036 (2) | 0.042 (3) | −0.008 (2) | 0.011 (2) | −0.003 (2) |
C12 | 0.028 (3) | 0.030 (2) | 0.036 (3) | −0.0008 (19) | −0.001 (2) | 0.002 (2) |
C20 | 0.031 (3) | 0.040 (2) | 0.032 (3) | 0.0047 (19) | 0.001 (2) | 0.0019 (19) |
C15 | 0.071 (4) | 0.049 (3) | 0.057 (4) | 0.010 (3) | 0.001 (3) | −0.021 (3) |
C4 | 0.052 (3) | 0.047 (3) | 0.052 (4) | 0.003 (2) | −0.007 (3) | −0.020 (2) |
C13 | 0.048 (3) | 0.041 (2) | 0.044 (3) | 0.008 (2) | −0.001 (2) | −0.006 (2) |
C14 | 0.054 (4) | 0.041 (2) | 0.074 (4) | 0.012 (2) | 0.008 (3) | 0.001 (3) |
C3 | 0.051 (3) | 0.035 (2) | 0.070 (4) | −0.013 (2) | 0.002 (3) | −0.011 (2) |
Ni1—O1 | 1.9922 (19) | C11—H11B | 0.9700 |
Ni1—O5 | 1.998 (2) | C19—C22 | 1.521 (4) |
Ni1—N1 | 2.015 (2) | C19—C21 | 1.531 (4) |
Ni1—N2 | 2.028 (3) | C19—C20 | 1.541 (4) |
Ni1—O4 | 2.143 (2) | C16—C15 | 1.367 (4) |
Ni1—O7 | 2.170 (2) | C16—H16A | 0.9300 |
N1—C7 | 1.280 (3) | C10—C8 | 1.519 (4) |
N1—C8 | 1.481 (3) | C10—H10A | 0.9700 |
N2—C18 | 1.283 (3) | C10—H10B | 0.9700 |
N2—C19 | 1.481 (3) | C22—H22A | 0.9700 |
O7—C21 | 1.435 (3) | C22—H22B | 0.9700 |
O7—H7B | 0.823 (10) | C8—C9 | 1.543 (4) |
O4—C11 | 1.434 (4) | C18—H18A | 0.9300 |
O4—H4B | 0.813 (10) | C6—C5 | 1.404 (4) |
O1—C1 | 1.305 (3) | C6—C7 | 1.441 (4) |
O5—C12 | 1.311 (4) | C5—C4 | 1.373 (4) |
O3—C10 | 1.417 (4) | C5—H5A | 0.9300 |
O3—H3A | 0.829 (10) | C7—H7A | 0.9300 |
O8—C22 | 1.416 (4) | C21—H21A | 0.9700 |
O8—H8A | 0.824 (10) | C21—H21B | 0.9700 |
O2—C9 | 1.424 (4) | C9—H9A | 0.9700 |
O2—H2A | 0.816 (10) | C9—H9B | 0.9700 |
O6—C20 | 1.429 (4) | C2—C3 | 1.374 (4) |
O6—H6A | 0.821 (10) | C2—H2B | 0.9300 |
O9—C23 | 1.361 (4) | C12—C13 | 1.399 (4) |
O9—H9 | 0.818 (10) | C20—H20A | 0.9700 |
C23—H23A | 0.9600 | C20—H20B | 0.9700 |
C23—H23B | 0.9600 | C15—C14 | 1.409 (5) |
C23—H23C | 0.9600 | C15—H15A | 0.9300 |
C1—C2 | 1.408 (4) | C4—C3 | 1.385 (4) |
C1—C6 | 1.421 (4) | C4—H4A | 0.9300 |
C17—C12 | 1.393 (4) | C13—C14 | 1.381 (4) |
C17—C16 | 1.406 (4) | C13—H13A | 0.9300 |
C17—C18 | 1.471 (4) | C14—H14A | 0.9300 |
C11—C8 | 1.537 (4) | C3—H3B | 0.9300 |
C11—H11A | 0.9700 | ||
O1—Ni1—O5 | 89.72 (9) | C8—C10—H10B | 109.7 |
O1—Ni1—N1 | 90.92 (10) | H10A—C10—H10B | 108.2 |
O5—Ni1—N1 | 98.84 (10) | O8—C22—C19 | 109.1 (3) |
O1—Ni1—N2 | 95.34 (9) | O8—C22—H22A | 109.9 |
O5—Ni1—N2 | 91.56 (10) | C19—C22—H22A | 109.9 |
N1—Ni1—N2 | 167.90 (12) | O8—C22—H22B | 109.9 |
O1—Ni1—O4 | 170.66 (9) | C19—C22—H22B | 109.9 |
O5—Ni1—O4 | 87.67 (9) | H22A—C22—H22B | 108.3 |
N1—Ni1—O4 | 80.64 (11) | N1—C8—C10 | 115.0 (3) |
N2—Ni1—O4 | 93.69 (10) | N1—C8—C11 | 106.9 (3) |
O1—Ni1—O7 | 94.71 (9) | C10—C8—C11 | 108.4 (3) |
O5—Ni1—O7 | 169.10 (10) | N1—C8—C9 | 107.3 (3) |
N1—Ni1—O7 | 91.05 (11) | C10—C8—C9 | 110.0 (3) |
N2—Ni1—O7 | 78.14 (11) | C11—C8—C9 | 109.1 (3) |
O4—Ni1—O7 | 89.45 (10) | N2—C18—C17 | 126.6 (3) |
C7—N1—C8 | 118.9 (3) | N2—C18—H18A | 116.7 |
C7—N1—Ni1 | 124.7 (2) | C17—C18—H18A | 116.7 |
C8—N1—Ni1 | 116.40 (19) | C5—C6—C1 | 119.5 (3) |
C18—N2—C19 | 121.2 (3) | C5—C6—C7 | 116.1 (3) |
C18—N2—Ni1 | 122.2 (2) | C1—C6—C7 | 124.4 (3) |
C19—N2—Ni1 | 116.0 (2) | C4—C5—C6 | 122.5 (4) |
C21—O7—Ni1 | 110.8 (2) | C4—C5—H5A | 118.8 |
C21—O7—H7B | 109 (2) | C6—C5—H5A | 118.8 |
Ni1—O7—H7B | 123 (2) | N1—C7—C6 | 126.6 (3) |
C11—O4—Ni1 | 110.07 (19) | N1—C7—H7A | 116.7 |
C11—O4—H4B | 108 (2) | C6—C7—H7A | 116.7 |
Ni1—O4—H4B | 121 (2) | O7—C21—C19 | 108.6 (3) |
C1—O1—Ni1 | 127.3 (2) | O7—C21—H21A | 110.0 |
C12—O5—Ni1 | 124.8 (2) | C19—C21—H21A | 110.0 |
C10—O3—H3A | 115 (3) | O7—C21—H21B | 110.0 |
C22—O8—H8A | 113 (3) | C19—C21—H21B | 110.0 |
C9—O2—H2A | 106 (3) | H21A—C21—H21B | 108.4 |
C20—O6—H6A | 111 (3) | O2—C9—C8 | 113.2 (3) |
C23—O9—H9 | 108 (3) | O2—C9—H9A | 108.9 |
O9—C23—H23A | 109.5 | C8—C9—H9A | 108.9 |
O9—C23—H23B | 109.5 | O2—C9—H9B | 108.9 |
H23A—C23—H23B | 109.5 | C8—C9—H9B | 108.9 |
O9—C23—H23C | 109.5 | H9A—C9—H9B | 107.8 |
H23A—C23—H23C | 109.5 | C3—C2—C1 | 121.8 (4) |
H23B—C23—H23C | 109.5 | C3—C2—H2B | 119.1 |
O1—C1—C2 | 119.9 (3) | C1—C2—H2B | 119.1 |
O1—C1—C6 | 123.3 (3) | O5—C12—C17 | 123.6 (3) |
C2—C1—C6 | 116.8 (3) | O5—C12—C13 | 118.4 (4) |
C12—C17—C16 | 120.3 (3) | C17—C12—C13 | 117.9 (3) |
C12—C17—C18 | 124.8 (3) | O6—C20—C19 | 111.5 (3) |
C16—C17—C18 | 114.7 (4) | O6—C20—H20A | 109.3 |
O4—C11—C8 | 112.4 (3) | C19—C20—H20A | 109.3 |
O4—C11—H11A | 109.1 | O6—C20—H20B | 109.3 |
C8—C11—H11A | 109.1 | C19—C20—H20B | 109.3 |
O4—C11—H11B | 109.1 | H20A—C20—H20B | 108.0 |
C8—C11—H11B | 109.1 | C16—C15—C14 | 116.5 (4) |
H11A—C11—H11B | 107.9 | C16—C15—H15A | 121.8 |
N2—C19—C22 | 114.3 (3) | C14—C15—H15A | 121.8 |
N2—C19—C21 | 104.8 (3) | C5—C4—C3 | 117.9 (4) |
C22—C19—C21 | 109.8 (3) | C5—C4—H4A | 121.1 |
N2—C19—C20 | 109.3 (3) | C3—C4—H4A | 121.1 |
C22—C19—C20 | 109.7 (3) | C14—C13—C12 | 120.5 (4) |
C21—C19—C20 | 108.6 (3) | C14—C13—H13A | 119.7 |
C15—C16—C17 | 122.6 (4) | C12—C13—H13A | 119.7 |
C15—C16—H16A | 118.7 | C13—C14—C15 | 122.3 (4) |
C17—C16—H16A | 118.7 | C13—C14—H14A | 118.9 |
O3—C10—C8 | 109.8 (3) | C15—C14—H14A | 118.9 |
O3—C10—H10A | 109.7 | C2—C3—C4 | 121.6 (4) |
C8—C10—H10A | 109.7 | C2—C3—H3B | 119.2 |
O3—C10—H10B | 109.7 | C4—C3—H3B | 119.2 |
O1—Ni1—N1—C7 | −14.5 (3) | C20—C19—C22—O8 | 61.9 (3) |
O5—Ni1—N1—C7 | −104.4 (3) | C7—N1—C8—C10 | −29.8 (4) |
N2—Ni1—N1—C7 | 106.7 (5) | Ni1—N1—C8—C10 | 149.3 (2) |
O4—Ni1—N1—C7 | 169.5 (3) | C7—N1—C8—C11 | −150.2 (3) |
O7—Ni1—N1—C7 | 80.2 (3) | Ni1—N1—C8—C11 | 28.9 (3) |
O1—Ni1—N1—C8 | 166.4 (2) | C7—N1—C8—C9 | 92.9 (3) |
O5—Ni1—N1—C8 | 76.6 (2) | Ni1—N1—C8—C9 | −88.0 (3) |
N2—Ni1—N1—C8 | −72.3 (5) | O3—C10—C8—N1 | −49.7 (4) |
O4—Ni1—N1—C8 | −9.6 (2) | O3—C10—C8—C11 | 69.9 (3) |
O7—Ni1—N1—C8 | −98.8 (2) | O3—C10—C8—C9 | −170.9 (2) |
O1—Ni1—N2—C18 | −111.1 (3) | O4—C11—C8—N1 | −40.6 (4) |
O5—Ni1—N2—C18 | −21.2 (3) | O4—C11—C8—C10 | −165.2 (3) |
N1—Ni1—N2—C18 | 128.1 (5) | O4—C11—C8—C9 | 75.1 (3) |
O4—Ni1—N2—C18 | 66.5 (3) | C19—N2—C18—C17 | 179.0 (3) |
O7—Ni1—N2—C18 | 155.2 (3) | Ni1—N2—C18—C17 | 8.9 (5) |
O1—Ni1—N2—C19 | 78.3 (2) | C12—C17—C18—N2 | 8.3 (6) |
O5—Ni1—N2—C19 | 168.17 (19) | C16—C17—C18—N2 | −176.3 (3) |
N1—Ni1—N2—C19 | −42.5 (5) | O1—C1—C6—C5 | 179.3 (3) |
O4—Ni1—N2—C19 | −104.1 (2) | C2—C1—C6—C5 | −0.8 (5) |
O7—Ni1—N2—C19 | −15.40 (19) | O1—C1—C6—C7 | −2.8 (5) |
O1—Ni1—O7—C21 | −108.8 (2) | C2—C1—C6—C7 | 177.1 (3) |
O5—Ni1—O7—C21 | 4.9 (6) | C1—C6—C5—C4 | −0.3 (5) |
N1—Ni1—O7—C21 | 160.2 (2) | C7—C6—C5—C4 | −178.4 (3) |
N2—Ni1—O7—C21 | −14.3 (2) | C8—N1—C7—C6 | −174.6 (3) |
O4—Ni1—O7—C21 | 79.6 (2) | Ni1—N1—C7—C6 | 6.4 (5) |
O1—Ni1—O4—C11 | −39.2 (7) | C5—C6—C7—N1 | −176.3 (3) |
O5—Ni1—O4—C11 | −113.1 (2) | C1—C6—C7—N1 | 5.7 (5) |
N1—Ni1—O4—C11 | −13.7 (2) | Ni1—O7—C21—C19 | 39.6 (3) |
N2—Ni1—O4—C11 | 155.5 (2) | N2—C19—C21—O7 | −50.3 (3) |
O7—Ni1—O4—C11 | 77.4 (2) | C22—C19—C21—O7 | −173.5 (2) |
O5—Ni1—O1—C1 | 116.5 (3) | C20—C19—C21—O7 | 66.4 (3) |
N1—Ni1—O1—C1 | 17.7 (3) | N1—C8—C9—O2 | −55.7 (3) |
N2—Ni1—O1—C1 | −151.9 (3) | C10—C8—C9—O2 | 70.0 (3) |
O4—Ni1—O1—C1 | 42.8 (7) | C11—C8—C9—O2 | −171.3 (3) |
O7—Ni1—O1—C1 | −73.4 (3) | O1—C1—C2—C3 | −179.2 (3) |
O1—Ni1—O5—C12 | 122.4 (2) | C6—C1—C2—C3 | 1.0 (5) |
N1—Ni1—O5—C12 | −146.7 (2) | Ni1—O5—C12—C17 | −19.4 (4) |
N2—Ni1—O5—C12 | 27.1 (2) | Ni1—O5—C12—C13 | 162.8 (2) |
O4—Ni1—O5—C12 | −66.6 (2) | C16—C17—C12—O5 | −177.8 (3) |
O7—Ni1—O5—C12 | 8.2 (6) | C18—C17—C12—O5 | −2.7 (5) |
Ni1—O1—C1—C2 | 168.0 (2) | C16—C17—C12—C13 | −0.1 (5) |
Ni1—O1—C1—C6 | −12.2 (5) | C18—C17—C12—C13 | 175.0 (3) |
Ni1—O4—C11—C8 | 33.7 (3) | N2—C19—C20—O6 | −67.4 (3) |
C18—N2—C19—C22 | −10.7 (4) | C22—C19—C20—O6 | 58.7 (3) |
Ni1—N2—C19—C22 | 160.0 (2) | C21—C19—C20—O6 | 178.8 (3) |
C18—N2—C19—C21 | −131.0 (3) | C17—C16—C15—C14 | 0.2 (6) |
Ni1—N2—C19—C21 | 39.7 (3) | C6—C5—C4—C3 | 1.3 (5) |
C18—N2—C19—C20 | 112.7 (3) | O5—C12—C13—C14 | 178.4 (3) |
Ni1—N2—C19—C20 | −76.6 (3) | C17—C12—C13—C14 | 0.6 (5) |
C12—C17—C16—C15 | −0.3 (6) | C12—C13—C14—C15 | −0.7 (6) |
C18—C17—C16—C15 | −175.9 (3) | C16—C15—C14—C13 | 0.3 (6) |
N2—C19—C22—O8 | −174.9 (3) | C1—C2—C3—C4 | 0.0 (6) |
C21—C19—C22—O8 | −57.5 (3) | C5—C4—C3—C2 | −1.2 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3A···O5i | 0.83 (1) | 1.76 (1) | 2.587 (3) | 173 (4) |
O7—H7B···O2i | 0.82 (1) | 2.02 (1) | 2.841 (4) | 177 (3) |
O8—H8A···O1ii | 0.82 (1) | 1.80 (1) | 2.616 (3) | 174 (4) |
O2—H2A···O3iii | 0.82 (1) | 1.90 (1) | 2.705 (3) | 172 (4) |
O6—H6A···O8iv | 0.82 (1) | 1.94 (1) | 2.749 (4) | 171 (4) |
O4—H4B···O9 | 0.81 (1) | 2.03 (1) | 2.831 (3) | 167 (3) |
O9—H9···O6v | 0.82 (1) | 2.20 (2) | 2.931 (3) | 148 (4) |
Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) x+1/2, y, −z+3/2; (iii) x−1/2, −y+1/2, −z+1; (iv) x−1/2, y, −z+3/2; (v) −x+1, y+1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | [Ni(C11H14NO4)2]·CH4O |
Mr | 539.22 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 293 |
a, b, c (Å) | 11.1900 (3), 18.8378 (5), 22.4202 (8) |
V (Å3) | 4726.1 (2) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.88 |
Crystal size (mm) | 0.1 × 0.08 × 0.08 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan (SORTAV; Blessing, 1995) |
Tmin, Tmax | 0.837, 0.962 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 8161, 4329, 1833 |
Rint | 0.093 |
(sin θ/λ)max (Å−1) | 0.602 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.063, 0.82 |
No. of reflections | 4329 |
No. of parameters | 340 |
No. of restraints | 7 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.38, −0.26 |
Computer programs: COLLECT (Nonius, 1998), HKL SCALEPACK (Otwinowski & Minor, 1997), HKL DENZO (Otwinowski & Minor, 1997) and maXus (Mackay et al., 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Sheldrick, 1998).
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3A···O5i | 0.829 (10) | 1.763 (11) | 2.587 (3) | 173 (4) |
O7—H7B···O2i | 0.823 (10) | 2.019 (11) | 2.841 (4) | 177 (3) |
O8—H8A···O1ii | 0.824 (10) | 1.795 (11) | 2.616 (3) | 174 (4) |
O2—H2A···O3iii | 0.816 (10) | 1.895 (12) | 2.705 (3) | 172 (4) |
O6—H6A···O8iv | 0.821 (10) | 1.936 (12) | 2.749 (4) | 171 (4) |
O4—H4B···O9 | 0.813 (10) | 2.032 (12) | 2.831 (3) | 167 (3) |
O9—H9···O6v | 0.818 (10) | 2.20 (2) | 2.931 (3) | 148 (4) |
Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) x+1/2, y, −z+3/2; (iii) x−1/2, −y+1/2, −z+1; (iv) x−1/2, y, −z+3/2; (v) −x+1, y+1/2, −z+3/2. |
Single-crystal X-ray diffraction analyses revealed that (I) is neutral, mononuclear molecule with the Ni(II) ion being octahedral coordination supplied by monoanionic and tridentate binding through the Ophen, Oalk and Nimi groups from two 2-[tris(hydroxymethyl)methyliminomethyl]phenolate ligands (Fig. 1). And The structure is isostructural with the zinc analog (Dey et al., 2002). Selected bond lengths and bond angels are listed in Table 1. Of the three –CH2OH groups, only one is bound to the nickel center, while the other two remain free. At the same time one methanol molecule is cocrystallized in this complex which makes abundant O—H···O hydrogen bonds (Table 2) between the molecules.
Mononuclear Cu(II) complex coordinatd by one chelate 2-[tris(hydroxymethyl)methyliminomethyl]phenolate was reported in crystal structure (Ni et al., 2005). And the isostructural zinc complex was reported by Dey et al. (2002).