Bis[1-(2-hydroxy­ethyl­imino­meth­yl)-2-naphtholato-κ²N,O]nickel(II)

The title nickel(II) complex, [Ni(C₁₃H₁₂NO₂)₂], has been synthesized by the reaction of a Schiff base ligand derived from 2-hydr­oxy-1-naphthaldehyde and 2-ethano­lamine with Ni(CH₃COO)₂·4H₂O. The asymmetric unit consists of half each of two independent mol­ecules which have similar geometries, with the Ni atom of each of the two neutral complex mol­ecules lying on an inversion centre. The coordination geometry around each Ni atom is square planar, with the two bidentate chelate Schiff base ligands coordinated through their imine N and phenol O atoms in a mutually trans configuration. The hydroxy O atoms do not coordinate to the Ni atom.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.007 Å
• R factor = 0.052
• wR factor = 0.124
• Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D       H2     ..  H4      ..       1.46 Ang.

Alert level C
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT341_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          7
PLAT480_ALERT_4_C Long H...A H-Bond Reported H22    ..  CG      ..       3.06 Ang.

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

   1 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
   1 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, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Bis[1-(2-hydroxyethyliminomethyl)-2-naphtholato-κ²N,O]nickel(II)

Crystal data

[Ni(C13H12NO2)2]	Z = 2
Mr = 487.18	F(000) = 508
Triclinic, P1	Dx = 1.501 Mg m^−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 10.227 (4) Å	Cell parameters from 1179 reflections
b = 10.288 (4) Å	θ = 2.3–22.9°
c = 12.119 (5) Å	µ = 0.94 mm^−1
α = 105.941 (6)°	T = 298 K
β = 109.636 (6)°	Plate, brown
γ = 103.438 (6)°	0.43 × 0.15 × 0.07 mm
V = 1077.9 (8) Å^3

Data collection

Bruker CCD area-detector diffractometer	3748 independent reflections
Radiation source: fine-focus sealed tube	2236 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.033
φ and ω scans	θmax = 25.0°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→12
Tmin = 0.689, Tmax = 0.937	k = −12→11
5658 measured reflections	l = −9→14

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.124	H-atom parameters constrained
S = 1.01	w = 1/[σ^2(Fo^2) + (0.0506P)^2] where P = (Fo^2 + 2Fc^2)/3
3748 reflections	(Δ/σ)max < 0.001
303 parameters	Δρmax = 0.50 e Å^−3
0 restraints	Δρmin = −0.30 e Å^−3

Special details

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
Ni1	0.0000	0.0000	0.0000	0.0314 (3)
Ni2	0.0000	0.5000	0.0000	0.0330 (3)
N1	−0.0851 (4)	−0.0351 (4)	0.1114 (3)	0.0353 (10)
N2	0.1562 (4)	0.6843 (4)	0.0976 (3)	0.0335 (9)
O1	0.1856 (3)	0.0917 (3)	0.1310 (3)	0.0444 (9)
O2	−0.3824 (4)	−0.3974 (4)	−0.0462 (4)	0.0641 (11)
H2	−0.3786	−0.4741	−0.0403	0.096*
O3	0.0423 (3)	0.4496 (3)	0.1370 (3)	0.0423 (9)
O4	0.4286 (4)	0.6830 (4)	0.0602 (4)	0.0575 (10)
H4	0.4010	0.6274	0.0918	0.086*
C1	−0.0208 (5)	0.0252 (5)	0.2335 (4)	0.0367 (12)
H1	−0.0769	0.0009	0.2763	0.044*
C2	0.1265 (5)	0.1245 (5)	0.3091 (4)	0.0336 (11)
C3	0.2240 (5)	0.1502 (5)	0.2530 (4)	0.0374 (12)
C4	0.3746 (5)	0.2429 (5)	0.3299 (5)	0.0483 (14)
H4A	0.4402	0.2578	0.2930	0.058*
C5	0.4234 (5)	0.3104 (5)	0.4582 (5)	0.0487 (14)
H5	0.5228	0.3697	0.5072	0.058*
C6	0.3294 (5)	0.2934 (5)	0.5177 (5)	0.0404 (12)
C7	0.3816 (6)	0.3715 (5)	0.6492 (5)	0.0515 (15)
H7	0.4804	0.4331	0.6967	0.062*
C8	0.2886 (6)	0.3573 (6)	0.7071 (5)	0.0502 (14)
H8	0.3237	0.4095	0.7937	0.060*
C9	0.1416 (6)	0.2648 (6)	0.6366 (4)	0.0505 (14)
H9	0.0790	0.2552	0.6768	0.061*
C10	0.0866 (6)	0.1872 (5)	0.5086 (4)	0.0425 (13)
H10	−0.0125	0.1260	0.4636	0.051*
C11	0.1791 (5)	0.1991 (5)	0.4441 (4)	0.0361 (12)
C12	−0.2377 (5)	−0.1449 (5)	0.0568 (4)	0.0455 (13)
H12A	−0.3039	−0.1275	−0.0118	0.055*
H12B	−0.2744	−0.1351	0.1216	0.055*
C13	−0.2380 (5)	−0.2961 (5)	0.0072 (5)	0.0455 (13)
H13A	−0.1994	−0.3056	−0.0564	0.055*
H13B	−0.1740	−0.3147	0.0761	0.055*
C14	0.2134 (5)	0.7447 (5)	0.2200 (4)	0.0354 (12)
H14	0.2815	0.8391	0.2570	0.043*
C15	0.1833 (5)	0.6820 (5)	0.3049 (4)	0.0336 (11)
C16	0.1049 (5)	0.5329 (5)	0.2570 (4)	0.0334 (11)
C17	0.0928 (5)	0.4656 (5)	0.3429 (4)	0.0411 (12)
H17	0.0428	0.3662	0.3119	0.049*
C18	0.1525 (5)	0.5435 (5)	0.4680 (5)	0.0438 (13)
H18	0.1459	0.4959	0.5222	0.053*
C19	0.2254 (5)	0.6960 (5)	0.5206 (4)	0.0374 (12)
C20	0.2812 (5)	0.7759 (6)	0.6517 (5)	0.0492 (14)
H20	0.2696	0.7282	0.7047	0.059*
C21	0.3517 (6)	0.9220 (7)	0.7019 (5)	0.0583 (16)
H21	0.3894	0.9736	0.7888	0.070*
C22	0.3670 (5)	0.9934 (6)	0.6227 (5)	0.0532 (15)
H22	0.4136	1.0936	0.6569	0.064*
C23	0.3143 (5)	0.9184 (5)	0.4946 (4)	0.0434 (13)
H23	0.3264	0.9686	0.4434	0.052*
C24	0.2427 (5)	0.7673 (5)	0.4394 (4)	0.0350 (11)
C25	0.2215 (5)	0.7673 (5)	0.0351 (4)	0.0407 (12)
H25A	0.2897	0.8626	0.0977	0.049*
H25B	0.1429	0.7801	−0.0282	0.049*
C26	0.3029 (6)	0.6942 (6)	−0.0275 (5)	0.0489 (14)
H26A	0.2354	0.5979	−0.0883	0.059*
H26B	0.3351	0.7481	−0.0738	0.059*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0309 (5)	0.0280 (5)	0.0311 (5)	0.0066 (4)	0.0148 (4)	0.0069 (4)
Ni2	0.0401 (5)	0.0261 (5)	0.0344 (5)	0.0110 (4)	0.0181 (4)	0.0118 (4)
N1	0.034 (2)	0.030 (2)	0.037 (2)	0.0081 (18)	0.0156 (19)	0.0077 (19)
N2	0.040 (2)	0.030 (2)	0.036 (2)	0.0119 (18)	0.0208 (19)	0.0134 (19)
O1	0.0331 (19)	0.054 (2)	0.036 (2)	0.0088 (16)	0.0135 (15)	0.0106 (17)
O2	0.057 (2)	0.038 (2)	0.071 (3)	−0.0042 (19)	0.019 (2)	0.012 (2)
O3	0.054 (2)	0.0319 (19)	0.036 (2)	0.0123 (17)	0.0177 (17)	0.0100 (16)
O4	0.048 (2)	0.059 (3)	0.070 (3)	0.0151 (19)	0.028 (2)	0.031 (2)
C1	0.037 (3)	0.033 (3)	0.037 (3)	0.011 (2)	0.016 (2)	0.012 (2)
C2	0.039 (3)	0.025 (3)	0.037 (3)	0.010 (2)	0.016 (2)	0.013 (2)
C3	0.029 (3)	0.031 (3)	0.034 (3)	0.006 (2)	0.002 (2)	0.003 (2)
C4	0.037 (3)	0.052 (3)	0.045 (3)	0.007 (3)	0.016 (2)	0.012 (3)
C5	0.034 (3)	0.045 (3)	0.049 (3)	0.007 (2)	0.006 (3)	0.013 (3)
C6	0.044 (3)	0.040 (3)	0.041 (3)	0.020 (3)	0.018 (3)	0.017 (3)
C7	0.051 (3)	0.046 (3)	0.039 (3)	0.016 (3)	0.003 (3)	0.010 (3)
C8	0.057 (4)	0.057 (4)	0.033 (3)	0.023 (3)	0.017 (3)	0.012 (3)
C9	0.058 (4)	0.060 (4)	0.037 (3)	0.027 (3)	0.021 (3)	0.018 (3)
C10	0.054 (3)	0.042 (3)	0.038 (3)	0.023 (3)	0.022 (3)	0.017 (3)
C11	0.039 (3)	0.030 (3)	0.035 (3)	0.014 (2)	0.009 (2)	0.013 (2)
C12	0.042 (3)	0.040 (3)	0.046 (3)	0.000 (3)	0.026 (2)	0.007 (3)
C13	0.041 (3)	0.033 (3)	0.049 (3)	−0.003 (2)	0.020 (3)	0.009 (2)
C14	0.035 (3)	0.021 (3)	0.047 (3)	0.008 (2)	0.019 (2)	0.009 (2)
C15	0.033 (3)	0.035 (3)	0.041 (3)	0.016 (2)	0.019 (2)	0.018 (2)
C16	0.035 (3)	0.032 (3)	0.040 (3)	0.015 (2)	0.019 (2)	0.019 (2)
C17	0.049 (3)	0.037 (3)	0.044 (3)	0.018 (3)	0.021 (3)	0.022 (3)
C18	0.047 (3)	0.053 (4)	0.043 (3)	0.024 (3)	0.021 (3)	0.028 (3)
C19	0.039 (3)	0.045 (3)	0.032 (3)	0.020 (3)	0.016 (2)	0.015 (2)
C20	0.058 (4)	0.060 (4)	0.034 (3)	0.026 (3)	0.021 (3)	0.021 (3)
C21	0.061 (4)	0.070 (4)	0.033 (3)	0.028 (3)	0.012 (3)	0.009 (3)
C22	0.056 (4)	0.043 (3)	0.048 (4)	0.017 (3)	0.015 (3)	0.009 (3)
C23	0.048 (3)	0.042 (3)	0.036 (3)	0.016 (3)	0.016 (2)	0.013 (3)
C24	0.035 (3)	0.038 (3)	0.034 (3)	0.015 (2)	0.016 (2)	0.013 (2)
C25	0.050 (3)	0.027 (3)	0.044 (3)	0.010 (2)	0.019 (3)	0.015 (2)
C26	0.061 (4)	0.049 (3)	0.047 (3)	0.014 (3)	0.034 (3)	0.024 (3)

Geometric parameters (Å, º)

Ni1—O1^i	1.826 (3)	C9—C10	1.372 (6)
Ni1—O1	1.826 (3)	C9—H9	0.9300
Ni1—N1^i	1.904 (4)	C10—C11	1.420 (6)
Ni1—N1	1.904 (4)	C10—H10	0.9300
Ni2—O3^ii	1.818 (3)	C12—C13	1.505 (6)
Ni2—O3	1.818 (3)	C12—H12A	0.9700
Ni2—N2	1.907 (4)	C12—H12B	0.9700
Ni2—N2^ii	1.907 (4)	C13—H13A	0.9700
N1—C1	1.288 (5)	C13—H13B	0.9700
N1—C12	1.491 (5)	C14—C15	1.432 (6)
N2—C14	1.292 (5)	C14—H14	0.9300
N2—C25	1.477 (6)	C15—C16	1.400 (6)
O1—C3	1.309 (5)	C15—C24	1.448 (6)
O2—C13	1.398 (5)	C16—C17	1.422 (6)
O2—H2	0.8200	C17—C18	1.341 (6)
O3—C16	1.301 (5)	C17—H17	0.9300
O4—C26	1.419 (5)	C18—C19	1.419 (6)
O4—H4	0.8200	C18—H18	0.9300
C1—C2	1.413 (6)	C19—C20	1.407 (6)
C1—H1	0.9300	C19—C24	1.411 (6)
C2—C3	1.399 (6)	C20—C21	1.359 (7)
C2—C11	1.442 (6)	C20—H20	0.9300
C3—C4	1.419 (6)	C21—C22	1.386 (7)
C4—C5	1.368 (6)	C21—H21	0.9300
C4—H4A	0.9300	C22—C23	1.372 (6)
C5—C6	1.390 (7)	C22—H22	0.9300
C5—H5	0.9300	C23—C24	1.404 (6)
C6—C7	1.413 (6)	C23—H23	0.9300
C6—C11	1.417 (6)	C25—C26	1.495 (6)
C7—C8	1.364 (7)	C25—H25A	0.9700
C7—H7	0.9300	C25—H25B	0.9700
C8—C9	1.386 (7)	C26—H26A	0.9700
C8—H8	0.9300	C26—H26B	0.9700
O1^i—Ni1—O1	180.0 (3)	N1—C12—H12A	109.4
O1^i—Ni1—N1^i	91.48 (15)	C13—C12—H12A	109.4
O1—Ni1—N1^i	88.53 (15)	N1—C12—H12B	109.4
O1^i—Ni1—N1	88.52 (15)	C13—C12—H12B	109.4
O1—Ni1—N1	91.47 (15)	H12A—C12—H12B	108.0
N1^i—Ni1—N1	180.0 (3)	O2—C13—C12	110.4 (4)
O3^ii—Ni2—O3	180.00 (17)	O2—C13—H13A	109.6
O3^ii—Ni2—N2	88.60 (15)	C12—C13—H13A	109.6
O3—Ni2—N2	91.40 (15)	O2—C13—H13B	109.6
O3^ii—Ni2—N2^ii	91.40 (15)	C12—C13—H13B	109.6
O3—Ni2—N2^ii	88.60 (15)	H13A—C13—H13B	108.1
N2—Ni2—N2^ii	180.0	N2—C14—C15	127.0 (4)
C1—N1—C12	115.1 (4)	N2—C14—H14	116.5
C1—N1—Ni1	125.7 (3)	C15—C14—H14	116.5
C12—N1—Ni1	119.1 (3)	C16—C15—C14	118.5 (4)
C14—N2—C25	115.4 (4)	C16—C15—C24	120.0 (4)
C14—N2—Ni2	124.0 (3)	C14—C15—C24	121.3 (4)
C25—N2—Ni2	120.7 (3)	O3—C16—C15	124.0 (4)
C3—O1—Ni1	129.2 (3)	O3—C16—C17	116.9 (4)
C13—O2—H2	109.5	C15—C16—C17	119.1 (4)
C16—O3—Ni2	128.9 (3)	C18—C17—C16	120.9 (5)
C26—O4—H4	109.5	C18—C17—H17	119.6
N1—C1—C2	126.6 (4)	C16—C17—H17	119.6
N1—C1—H1	116.7	C17—C18—C19	122.2 (5)
C2—C1—H1	116.7	C17—C18—H18	118.9
C3—C2—C1	119.7 (4)	C19—C18—H18	118.9
C3—C2—C11	119.2 (4)	C20—C19—C24	120.1 (5)
C1—C2—C11	121.0 (4)	C20—C19—C18	121.0 (5)
O1—C3—C2	123.8 (4)	C24—C19—C18	118.9 (4)
O1—C3—C4	116.4 (5)	C21—C20—C19	120.9 (5)
C2—C3—C4	119.8 (4)	C21—C20—H20	119.6
C5—C4—C3	120.1 (5)	C19—C20—H20	119.6
C5—C4—H4A	119.9	C20—C21—C22	119.6 (5)
C3—C4—H4A	119.9	C20—C21—H21	120.2
C4—C5—C6	122.2 (5)	C22—C21—H21	120.2
C4—C5—H5	118.9	C23—C22—C21	120.9 (5)
C6—C5—H5	118.9	C23—C22—H22	119.6
C5—C6—C7	120.6 (5)	C21—C22—H22	119.6
C5—C6—C11	119.1 (5)	C22—C23—C24	121.3 (5)
C7—C6—C11	120.3 (5)	C22—C23—H23	119.4
C8—C7—C6	120.6 (5)	C24—C23—H23	119.4
C8—C7—H7	119.7	C23—C24—C19	117.3 (4)
C6—C7—H7	119.7	C23—C24—C15	123.9 (4)
C7—C8—C9	119.7 (5)	C19—C24—C15	118.7 (4)
C7—C8—H8	120.1	N2—C25—C26	112.5 (4)
C9—C8—H8	120.1	N2—C25—H25A	109.1
C10—C9—C8	121.4 (5)	C26—C25—H25A	109.1
C10—C9—H9	119.3	N2—C25—H25B	109.1
C8—C9—H9	119.3	C26—C25—H25B	109.1
C9—C10—C11	120.9 (5)	H25A—C25—H25B	107.8
C9—C10—H10	119.6	O4—C26—C25	112.9 (4)
C11—C10—H10	119.6	O4—C26—H26A	109.0
C6—C11—C10	117.1 (4)	C25—C26—H26A	109.0
C6—C11—C2	119.4 (5)	O4—C26—H26B	109.0
C10—C11—C2	123.5 (4)	C25—C26—H26B	109.0
N1—C12—C13	111.2 (4)	H26A—C26—H26B	107.8

Symmetry codes: (i) −x, −y, −z; (ii) −x, −y+1, −z.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2···O4^i	0.82	2.01	2.813 (5)	164
O4—H4···O2^i	0.82	2.22	2.813 (5)	129
C18—H18···Cg	0.93	2.76 (1)	3.4914 (11)	136
C22—H22···Cg^iii	0.93	3.06 (1)	3.6071 (12)	119

Symmetry codes: (i) −x, −y, −z; (iii) x, y+1, z.