Bis­(pyridin-2-yl­methano­lato-κ²N,O)­bis­(tri­fluoro­acetato)­nickel(II)

The Ni^II atom in the title compound, [Ni(C₂F₃O₂)₂(C₆H₇NO)₂], is located on an inversion centre and is in an irregular coordination environment. Two tri­fluoro­acetate ions and two pyridin-2-yl­methanol mol­ecules coordinate to the Ni^II atom. The pyridin-2-yl­methanol ligand coordinates via its pyridyl N atom and its methanol O atom, resulting in a five-membered chelate ring. The ring is puckered in an envelope conformation, with the methanol O atom as flap. The tri­fluoro­acetate ions coordinate via one O atom only. The second O atom accepts a strong hydrogen bond from the methanol hydroxy group.

Key indicators

• Single-crystal X-ray study
• T = 110 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.036
• wR factor = 0.080
• Data-to-parameter ratio = 11.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low .......       0.98
PLAT164_ALERT_4_C Nr. of Refined C-H H-Atoms in Heavy-At Struct...          6
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.07 Ratio
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni     -   N1      ..       5.18 su

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   1 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
   1 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: X-SEED (Barbour, 2001) and SHELXTL (Bruker, 2000); software used to prepare material for publication: PLATON (Spek, 2003).

Bis(pyridin-2-ylmethanolato-κ²N,O)bis(trifluoroacetato)nickel(II)

Crystal data

[Ni(C2F3O2)2(C6H7NO)2]	F(000) = 1016
Mr = 503.00	Dx = 1.802 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 2173 reflections
a = 12.539 (3) Å	θ = 2.4–27.3°
b = 11.113 (2) Å	µ = 1.15 mm^−1
c = 13.315 (3) Å	T = 110 K
β = 92.23 (3)°	Prism, blue
V = 1854.0 (7) Å^3	0.29 × 0.26 × 0.13 mm
Z = 4

Data collection

Bruker SMART 1K CCD diffractometer	2012 independent reflections
Radiation source: fine-focus sealed tube	1769 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.024
ω scans	θmax = 27.2°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −16→14
Tmin = 0.733, Tmax = 0.865	k = −11→14
4350 measured reflections	l = −12→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.080	All H-atom parameters refined
S = 1.09	w = 1/[σ^2(Fo^2) + (0.022P)^2 + 5.385P] where P = (Fo^2 + 2Fc^2)/3
2012 reflections	(Δ/σ)max < 0.001
172 parameters	Δρmax = 0.35 e Å^−3
7 restraints	Δρmin = −0.38 e Å^−3

Special details

Experimental. The data collection covered approximately a hemisphere of reciprocal space, by a combination of three sets of exposures; each set having a different φ angle for the crystal and each exposure covering 0.3° in θ. Crystal decay was monitored by analyzing duplicate reflections, and found to be less than 1%, therefore no decay correction was applied.

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 (Ų)

	x	y	z	Uiso*/Ueq
Ni	0.2500	0.2500	0.5000	0.01265 (12)
C1	0.34235 (18)	0.3032 (2)	0.71040 (18)	0.0172 (5)
O1	0.29328 (13)	0.07126 (14)	0.48525 (12)	0.0168 (3)
H1	0.336 (2)	0.3867 (11)	0.6915 (19)	0.018 (7)*
N1	0.31343 (15)	0.21970 (17)	0.64123 (14)	0.0147 (4)
O2	0.10572 (13)	0.18645 (14)	0.55017 (12)	0.0175 (4)
O3	0.01950 (14)	0.36101 (15)	0.57662 (13)	0.0220 (4)
C2	0.3811 (2)	0.2721 (2)	0.80511 (18)	0.0208 (5)
H2	0.403 (2)	0.3328 (19)	0.8536 (17)	0.026 (7)*
C3	0.3905 (2)	0.1509 (2)	0.83010 (18)	0.0230 (5)
H3	0.417 (2)	0.129 (2)	0.8969 (11)	0.020 (7)*
C4	0.3623 (2)	0.0649 (2)	0.75832 (18)	0.0201 (5)
H4	0.371 (2)	−0.0200 (10)	0.7723 (19)	0.017 (7)*
C5	0.32437 (18)	0.1023 (2)	0.66449 (17)	0.0160 (5)
C6	0.2906 (2)	0.0153 (2)	0.58237 (17)	0.0180 (5)
H6B	0.2177 (10)	−0.010 (2)	0.5912 (18)	0.014 (6)*
H6A	0.3394 (18)	−0.0522 (17)	0.585 (2)	0.024 (7)*
C7	0.03009 (18)	0.2499 (2)	0.57750 (16)	0.0165 (4)
H7	0.3671 (11)	0.082 (3)	0.465 (2)	0.043 (9)*
C8	−0.0672 (2)	0.1794 (2)	0.61510 (18)	0.0207 (5)
F1	−0.14737 (13)	0.18349 (17)	0.54544 (12)	0.0377 (4)
F2	−0.10545 (12)	0.22762 (15)	0.69808 (11)	0.0295 (4)
F3	−0.04618 (14)	0.06529 (15)	0.63545 (16)	0.0455 (5)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni	0.0126 (2)	0.0130 (2)	0.0124 (2)	0.00082 (16)	0.00055 (14)	0.00089 (16)
C1	0.0137 (11)	0.0189 (11)	0.0193 (12)	0.0010 (9)	0.0025 (9)	−0.0004 (9)
O1	0.0178 (8)	0.0157 (8)	0.0167 (8)	−0.0002 (7)	−0.0002 (6)	0.0005 (6)
N1	0.0114 (9)	0.0160 (9)	0.0169 (9)	0.0001 (7)	0.0023 (7)	0.0015 (7)
O2	0.0154 (8)	0.0166 (8)	0.0207 (8)	0.0006 (6)	0.0031 (7)	0.0009 (6)
O3	0.0185 (9)	0.0182 (9)	0.0296 (9)	0.0015 (7)	0.0051 (7)	0.0003 (7)
C2	0.0189 (12)	0.0279 (14)	0.0155 (11)	−0.0020 (10)	0.0006 (9)	−0.0046 (9)
C3	0.0187 (12)	0.0342 (14)	0.0159 (11)	0.0004 (11)	−0.0017 (9)	0.0041 (10)
C4	0.0173 (12)	0.0234 (12)	0.0196 (12)	0.0004 (10)	0.0007 (9)	0.0066 (10)
C5	0.0113 (11)	0.0187 (11)	0.0182 (11)	−0.0008 (9)	0.0027 (9)	0.0016 (9)
C6	0.0200 (13)	0.0171 (11)	0.0169 (11)	0.0028 (9)	−0.0003 (9)	0.0030 (9)
C7	0.0132 (10)	0.0230 (11)	0.0132 (10)	−0.0002 (10)	−0.0002 (8)	−0.0013 (9)
C8	0.0166 (12)	0.0246 (13)	0.0211 (12)	−0.0017 (10)	0.0030 (9)	−0.0004 (10)
F1	0.0229 (8)	0.0663 (12)	0.0234 (8)	−0.0193 (8)	−0.0040 (7)	−0.0029 (8)
F2	0.0233 (8)	0.0454 (10)	0.0205 (7)	−0.0044 (7)	0.0082 (6)	−0.0013 (7)
F3	0.0351 (10)	0.0233 (9)	0.0798 (14)	−0.0005 (7)	0.0251 (9)	0.0134 (9)

Geometric parameters (Å, º)

Ni—N1	2.041 (2)	C2—C3	1.391 (4)
Ni—N1^i	2.041 (2)	C2—H2	0.967 (10)
Ni—O1	2.070 (2)	C3—C4	1.388 (4)
Ni—O1^i	2.0705 (16)	C3—H3	0.969 (10)
Ni—O2^i	2.077 (2)	C4—C5	1.383 (3)
Ni—O2	2.077 (2)	C4—H4	0.967 (10)
C1—N1	1.347 (3)	C5—C6	1.508 (3)
C1—C2	1.377 (3)	C6—H6B	0.967 (10)
C1—H1	0.964 (10)	C6—H6A	0.968 (10)
O1—C6	1.437 (3)	C7—C8	1.549 (3)
O1—H7	0.981 (10)	C8—F3	1.322 (3)
N1—C5	1.346 (3)	C8—F2	1.333 (3)
O2—C7	1.247 (3)	C8—F1	1.342 (3)
O3—C7	1.242 (3)
N1—Ni—N1^i	180.0	C4—C3—C2	119.0 (2)
N1—Ni—O1	80.50 (7)	C4—C3—H3	121.9 (16)
N1^i—Ni—O1	99.50 (7)	C2—C3—H3	119.1 (16)
N1^i—Ni—O1^i	80.50 (7)	C5—C4—C3	119.0 (2)
O1—Ni—O1^i	180.00 (9)	C5—C4—H4	119.8 (16)
N1—Ni—O2^i	92.26 (7)	C3—C4—H4	121.2 (15)
N1^i—Ni—O2^i	87.74 (7)	N1—C5—C4	121.8 (2)
O1—Ni—O2^i	93.50 (6)	N1—C5—C6	115.6 (2)
O1^i—Ni—O2^i	86.51 (6)	C4—C5—C6	122.6 (2)
N1—Ni—O2	87.74 (7)	O1—C6—C5	111.0 (2)
N1^i—Ni—O2	92.26 (7)	O1—C6—H6B	106.9 (15)
O1—Ni—O2	86.51 (6)	C5—C6—H6B	109.7 (15)
O2^i—Ni—O2	180.00 (4)	O1—C6—H6A	109.5 (17)
N1—C1—C2	122.0 (2)	C5—C6—H6A	108.0 (16)
N1—C1—H1	117.9 (16)	H6B—C6—H6A	112 (2)
C2—C1—H1	120.2 (16)	O3—C7—O2	129.9 (2)
C6—O1—Ni	108.34 (13)	O3—C7—C8	114.8 (2)
Ni—O1—H7	99 (2)	O2—C7—C8	115.2 (2)
C5—N1—C1	119.2 (2)	F3—C8—F2	106.9 (2)
C5—N1—Ni	113.8 (2)	F3—C8—F1	108.2 (2)
C1—N1—Ni	127.0 (2)	F2—C8—F1	106.0 (2)
C7—O2—Ni	125.70 (15)	F3—C8—C7	113.4 (2)
C1—C2—C3	119.0 (2)	F2—C8—C7	112.2 (2)
C1—C2—H2	121.2 (17)	F1—C8—C7	109.8 (2)
C3—C2—H2	119.8 (17)

Symmetry code: (i) −x+1/2, −y+1/2, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H7···O3^i	0.98 (1)	1.67 (1)	2.628 (2)	164 (3)

Symmetry code: (i) −x+1/2, −y+1/2, −z+1.