The two-dimensional network polymer of (ethanol)(μ₃-N-salicyclideneglycinato)nickel(II)

In the title complex, [Ni(C₉H₇NO₃)(C₂H₆O)]_n, each Ni atom is octa­hedrally coordinated by four O atoms and one N atom from three fully deprotonated N-salicylideneglycinate (salgly) anions and by one O atom from an ethanol mol­ecule. Two inversion-related Ni²⁺ ions are bridged by two O atoms from the phenolate groups of two salgly anions, forming a centrosymmetric dimeric unit which is further linked by carboxyl­ate O atoms to give a two-dimensional network coordination polymer in the bc plane.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.005 Å
• R factor = 0.034
• wR factor = 0.090
• Data-to-parameter ratio = 13.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT220_ALERT_2_B Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       4.21 Ratio

Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.13
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.90 Ratio
PLAT360_ALERT_2_C Short  C(sp3)-C(sp3) Bond  C10    -   C11    ...       1.40 Ang.

   0 ALERT level A = In general: serious problem
   1 ALERT level B = Potentially serious problem
   4 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
   3 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

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Computing details

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Sheldrick, 1997b); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(ethanol)(µ₃-N-salicyclideneglycinato)nickel(II)

Crystal data

[Ni(C9H7NO3)(C2H6O)]	F(000) = 584
Mr = 281.93	Dx = 1.656 Mg m^−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 29 reflections
a = 11.656 (3) Å	θ = 3.1–13.7°
b = 7.326 (2) Å	µ = 1.72 mm^−1
c = 14.012 (2) Å	T = 296 K
β = 109.09 (1)°	Block, green
V = 1130.7 (4) Å^3	0.40 × 0.32 × 0.18 mm
Z = 4

Data collection

Siemens P4 diffractometer	1659 reflections with I > 2σ(I)
Radiation source: normal-focus sealed tube	Rint = 0.019
Graphite monochromator	θmax = 25.5°, θmin = 1.9°
ω scans	h = 0→14
Absorption correction: ψ scan (North et al., 1968)	k = 0→8
Tmin = 0.538, Tmax = 0.734	l = −16→16
2476 measured reflections	3 standard reflections every 97 reflections
2102 independent reflections	intensity decay: 2.2%

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.090	w = 1/[σ^2(Fo^2) + (0.0531P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 1.00	(Δ/σ)max < 0.001
2102 reflections	Δρmax = 0.90 e Å^−3
160 parameters	Δρmin = −0.42 e Å^−3
1 restraint	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0068 (10)

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	0.52933 (3)	0.46211 (6)	0.40173 (3)	0.02223 (16)
O1	0.60914 (18)	0.5734 (3)	0.53924 (15)	0.0243 (5)
O2	0.4785 (2)	0.3196 (3)	0.26788 (15)	0.0307 (5)
O3	0.5565 (2)	0.2106 (3)	0.15334 (15)	0.0313 (5)
N1	0.6760 (2)	0.5053 (3)	0.36285 (19)	0.0258 (6)
C1	0.7264 (3)	0.6031 (4)	0.5819 (2)	0.0240 (7)
C2	0.7743 (3)	0.6305 (5)	0.6865 (2)	0.0351 (8)
H2	0.7234	0.6213	0.7254	0.042*
C3	0.8962 (3)	0.6710 (6)	0.7331 (3)	0.0495 (11)
H3	0.9261	0.6850	0.8029	0.059*
C4	0.9734 (3)	0.6906 (6)	0.6777 (3)	0.0494 (11)
H4A	1.0538	0.7246	0.7088	0.059*
C5	0.9299 (3)	0.6594 (5)	0.5763 (3)	0.0383 (9)
H5	0.9826	0.6696	0.5391	0.046*
C6	0.8080 (3)	0.6121 (4)	0.5259 (2)	0.0267 (7)
C7	0.7776 (3)	0.5664 (4)	0.4195 (2)	0.0262 (7)
H7	0.8378	0.5833	0.3902	0.031*
C8	0.6610 (3)	0.4487 (5)	0.2594 (2)	0.0300 (7)
H8A	0.7350	0.3915	0.2569	0.036*
H8B	0.6447	0.5545	0.2153	0.036*
C9	0.5561 (3)	0.3147 (4)	0.2243 (2)	0.0255 (7)
O4	0.5864 (3)	0.2007 (3)	0.47130 (19)	0.0437 (7)
H4	0.585 (3)	0.203 (5)	0.5292 (11)	0.037 (11)*
C10	0.6739 (4)	0.0709 (6)	0.4646 (4)	0.0627 (13)
H10A	0.6512	−0.0481	0.4828	0.075*
H10B	0.6722	0.0644	0.3950	0.075*
C11	0.7927 (5)	0.1097 (8)	0.5261 (5)	0.100 (2)
H11A	0.8036	0.2395	0.5327	0.121*
H11B	0.8490	0.0596	0.4961	0.121*
H11C	0.8070	0.0565	0.5915	0.121*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Ni1	0.0252 (2)	0.0262 (2)	0.0176 (2)	−0.00220 (18)	0.01019 (16)	−0.00197 (17)
O1	0.0235 (11)	0.0314 (13)	0.0190 (11)	−0.0044 (9)	0.0084 (9)	−0.0021 (9)
O2	0.0311 (13)	0.0393 (14)	0.0252 (12)	−0.0067 (11)	0.0140 (10)	−0.0098 (10)
O3	0.0426 (14)	0.0313 (13)	0.0256 (12)	−0.0047 (11)	0.0186 (11)	−0.0074 (10)
N1	0.0315 (15)	0.0257 (15)	0.0242 (13)	−0.0013 (11)	0.0144 (12)	−0.0038 (11)
C1	0.0251 (16)	0.0181 (15)	0.0289 (16)	0.0017 (13)	0.0088 (14)	−0.0010 (13)
C2	0.0295 (19)	0.044 (2)	0.0296 (18)	0.0061 (17)	0.0065 (15)	−0.0064 (16)
C3	0.033 (2)	0.071 (3)	0.035 (2)	0.010 (2)	−0.0023 (17)	−0.019 (2)
C4	0.0219 (19)	0.066 (3)	0.051 (2)	0.0036 (19)	−0.0013 (18)	−0.021 (2)
C5	0.0237 (17)	0.045 (2)	0.047 (2)	−0.0012 (16)	0.0119 (16)	−0.0114 (17)
C6	0.0251 (17)	0.0235 (16)	0.0301 (17)	−0.0008 (14)	0.0072 (14)	−0.0035 (14)
C7	0.0258 (17)	0.0266 (18)	0.0297 (17)	−0.0020 (14)	0.0137 (14)	−0.0012 (13)
C8	0.0356 (18)	0.0331 (18)	0.0278 (17)	−0.0044 (16)	0.0193 (15)	−0.0049 (14)
C9	0.0319 (18)	0.0247 (17)	0.0190 (15)	0.0008 (14)	0.0070 (14)	0.0013 (13)
O4	0.0673 (19)	0.0375 (15)	0.0369 (15)	0.0165 (13)	0.0314 (14)	0.0093 (12)
C10	0.064 (3)	0.048 (3)	0.078 (3)	0.015 (2)	0.024 (3)	0.003 (2)
C11	0.086 (4)	0.058 (3)	0.146 (6)	0.006 (3)	0.021 (4)	0.017 (4)

Geometric parameters (Å, º)

Ni1—N1	1.982 (3)	C3—H3	0.93
Ni1—O1	2.017 (2)	C4—C5	1.363 (5)
Ni1—O1^i	2.057 (2)	C4—H4A	0.93
Ni1—O2	2.057 (2)	C5—C6	1.407 (4)
Ni1—O3^ii	2.099 (2)	C5—H5	0.93
Ni1—O4	2.153 (3)	C6—C7	1.455 (4)
O1—C1	1.319 (4)	C7—H7	0.93
O1—Ni1^i	2.057 (2)	C8—C9	1.520 (4)
O2—C9	1.247 (4)	C8—H8A	0.97
O3—C9	1.254 (3)	C8—H8B	0.97
O3—Ni1^iii	2.099 (2)	O4—C10	1.420 (5)
N1—C7	1.272 (4)	O4—H4	0.815 (10)
N1—C8	1.462 (4)	C10—C11	1.399 (6)
C1—C2	1.403 (4)	C10—H10A	0.97
C1—C6	1.418 (4)	C10—H10B	0.97
C2—C3	1.388 (5)	C11—H11A	0.96
C2—H2	0.93	C11—H11B	0.96
C3—C4	1.375 (5)	C11—H11C	0.96
N1—Ni1—O1	91.62 (9)	C3—C4—H4A	120.6
N1—Ni1—O1^i	172.55 (9)	C4—C5—C6	122.3 (3)
O1—Ni1—O1^i	81.05 (9)	C4—C5—H5	118.8
N1—Ni1—O2	81.23 (9)	C6—C5—H5	118.8
O1—Ni1—O2	168.87 (9)	C5—C6—C1	118.9 (3)
O1^i—Ni1—O2	105.82 (8)	C5—C6—C7	116.0 (3)
N1—Ni1—O3^ii	96.35 (10)	C1—C6—C7	125.0 (3)
O1—Ni1—O3^ii	90.92 (9)	N1—C7—C6	125.8 (3)
O1^i—Ni1—O3^ii	85.13 (8)	N1—C7—H7	117.1
O2—Ni1—O3^ii	98.30 (9)	C6—C7—H7	117.1
N1—Ni1—O4	95.75 (10)	N1—C8—C9	109.1 (2)
O1—Ni1—O4	87.10 (9)	N1—C8—H8A	109.9
O1^i—Ni1—O4	82.66 (9)	C9—C8—H8A	109.9
O2—Ni1—O4	85.16 (10)	N1—C8—H8B	109.9
O3^ii—Ni1—O4	167.79 (9)	C9—C8—H8B	109.9
C1—O1—Ni1	125.81 (18)	H8A—C8—H8B	108.3
C1—O1—Ni1^i	132.25 (18)	O2—C9—O3	126.7 (3)
Ni1—O1—Ni1^i	98.95 (9)	O2—C9—C8	117.3 (3)
C9—O2—Ni1	115.0 (2)	O3—C9—C8	116.0 (3)
C9—O3—Ni1^iii	134.0 (2)	C10—O4—Ni1	133.4 (3)
C7—N1—C8	120.2 (3)	C10—O4—H4	109 (3)
C7—N1—Ni1	126.5 (2)	Ni1—O4—H4	109 (3)
C8—N1—Ni1	113.18 (19)	C11—C10—O4	114.3 (4)
O1—C1—C2	119.8 (3)	C11—C10—H10A	108.7
O1—C1—C6	122.7 (3)	O4—C10—H10A	108.7
C2—C1—C6	117.5 (3)	C11—C10—H10B	108.7
C3—C2—C1	121.2 (3)	O4—C10—H10B	108.7
C3—C2—H2	119.4	H10A—C10—H10B	107.6
C1—C2—H2	119.4	C10—C11—H11A	109.5
C4—C3—C2	121.0 (3)	C10—C11—H11B	109.5
C4—C3—H3	119.5	H11A—C11—H11B	109.5
C2—C3—H3	119.5	C10—C11—H11C	109.5
C5—C4—C3	118.9 (3)	H11A—C11—H11C	109.5
C5—C4—H4A	120.6	H11B—C11—H11C	109.5
N1—Ni1—O1—C1	−16.3 (2)	C1—C2—C3—C4	1.8 (6)
O1^i—Ni1—O1—C1	162.4 (3)	C2—C3—C4—C5	−3.7 (6)
O2—Ni1—O1—C1	33.4 (6)	C3—C4—C5—C6	1.6 (6)
O3^ii—Ni1—O1—C1	−112.7 (2)	C4—C5—C6—C1	2.3 (6)
O4—Ni1—O1—C1	79.4 (2)	C4—C5—C6—C7	−174.5 (3)
N1—Ni1—O1—Ni1^i	−178.69 (10)	O1—C1—C6—C5	174.8 (3)
O2—Ni1—O1—Ni1^i	−128.9 (4)	C2—C1—C6—C5	−4.1 (5)
O3^ii—Ni1—O1—Ni1^i	84.92 (9)	O1—C1—C6—C7	−8.8 (5)
O4—Ni1—O1—Ni1^i	−83.02 (10)	C2—C1—C6—C7	172.4 (3)
N1—Ni1—O2—C9	2.4 (2)	C8—N1—C7—C6	−174.3 (3)
O1—Ni1—O2—C9	−48.1 (5)	Ni1—N1—C7—C6	2.0 (5)
O1^i—Ni1—O2—C9	−175.1 (2)	C5—C6—C7—N1	173.6 (3)
O3^ii—Ni1—O2—C9	97.6 (2)	C1—C6—C7—N1	−3.0 (5)
O4—Ni1—O2—C9	−94.2 (2)	C7—N1—C8—C9	157.0 (3)
O1—Ni1—N1—C7	5.6 (3)	Ni1—N1—C8—C9	−19.7 (3)
O2—Ni1—N1—C7	−165.9 (3)	Ni1—O2—C9—O3	165.6 (3)
O3^ii—Ni1—N1—C7	96.7 (3)	Ni1—O2—C9—C8	−14.8 (3)
O4—Ni1—N1—C7	−81.7 (3)	Ni1^iii—O3—C9—O2	−19.4 (5)
O1—Ni1—N1—C8	−178.0 (2)	Ni1^iii—O3—C9—C8	161.0 (2)
O2—Ni1—N1—C8	10.6 (2)	N1—C8—C9—O2	22.9 (4)
O3^ii—Ni1—N1—C8	−86.9 (2)	N1—C8—C9—O3	−157.5 (3)
O4—Ni1—N1—C8	94.8 (2)	N1—Ni1—O4—C10	−19.0 (4)
Ni1—O1—C1—C2	−161.5 (2)	O1—Ni1—O4—C10	−110.3 (4)
Ni1^i—O1—C1—C2	−5.3 (5)	O1^i—Ni1—O4—C10	168.4 (4)
Ni1—O1—C1—C6	19.7 (4)	O2—Ni1—O4—C10	61.7 (4)
Ni1^i—O1—C1—C6	175.9 (2)	O3^ii—Ni1—O4—C10	168.8 (4)
O1—C1—C2—C3	−176.8 (3)	Ni1—O4—C10—C11	82.4 (5)
C6—C1—C2—C3	2.1 (5)

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, y+1/2, −z+1/2; (iii) −x+1, y−1/2, −z+1/2.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4···O3^iv	0.82 (1)	1.98 (2)	2.762 (3)	161 (4)

Symmetry code: (iv) x, −y+1/2, z+1/2.