Bis{2-[tris­(hydroxy­meth­yl)methyl­imino­meth­yl]phenolato-κ3N,O,O′}nickel(II) methanol solvate

Wang, Q.; Li, X.; Wang, X.; Zhang, Y.

doi:10.1107/S160053680704384X

Bis{2-[tris(hydroxymethyl)methyliminomethyl]phenolato-κ³N,O,O′}nickel(II) methanol solvate

In the crystal structure of [Ni(C₁₁H₁₄NO₄)₂]·CH₄O, the 2-[tris(hydroxymethyl)methyliminomethyl]phenolate monoanions bind in a tridentate mode through the phenolate, alcohol and imine donor atoms to confer an octahedral geometry on nickel. Adjacent molecules are linked by O—H

O hydrogen bonds into a three-dimensional supramolecular network structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680704384X/ng2321sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680704384X/ng2321Isup2.hkl Contains datablock I

CCDC reference: 663600

checkCIF report

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

Comment top

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 O_phen, O_alk and N_imi 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).

Related literature top

See Dey et al. (2002) for the isostructural zinc analog. For a related Cu^II complex, see Ni (2005).

Experimental top

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.

Structure description top

See Dey et al. (2002) for the isostructural zinc analog. For a related Cu^II complex, see Ni (2005).

Computing details top

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).

Figures top

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.

Bis{2-[tris(hydroxymethyl)methyliminomethyl]phenolato-κ3 N,O,O'}nickel(II) methanol solvate top

Crystal data top

[Ni(C₁₁H₁₄NO₄)₂]·CH₄O	D_x = 1.516 Mg m⁻³
M_r = 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

Data collection top

Nonius KappaCCD diffractometer	4329 independent reflections
Radiation source: fine-focus sealed tube	1833 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.093
Detector resolution: 0.76 pixels mm^-1	θ_max = 25.4°, θ_min = 3.5°
CCD scans	h = −13→13
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	k = −22→22
T_min = 0.837, T_max = 0.962	l = −26→27
8161 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)] = 0.040	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(F_o²) + (0.0165P)²] where P = (F_o² + 2F_c²)/3
4329 reflections	(Δ/σ)_max = 0.001
340 parameters	Δρ_max = 0.38 e Å⁻³
7 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

[Ni(C₁₁H₁₄NO₄)₂]·CH₄O	V = 4726.1 (2) Å³
M_r = 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

Data collection top

Nonius KappaCCD diffractometer	4329 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1995)	1833 reflections with I > 2σ(I)
T_min = 0.837, T_max = 0.962	R_int = 0.093
8161 measured reflections

Refinement top

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	Δρ_max = 0.38 e Å⁻³
4329 reflections	Δρ_min = −0.26 e Å⁻³
340 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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···O8^iv	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···O6^v	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
M_r	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)
T_min, T_max	0.837, 0.962
No. of measured, independent and observed [I > 2σ(I)] reflections	8161, 4329, 1833
R_int	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
Δρ_max, Δρ_min (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).