Literature DB >> 22589818

trans-Diaqua-bis-(l-phenyl-alaninato-κ(2)N,O)nickel(II).

Massomeh Ghorbanloo, Nahid Shahbakhsh, Duane Choquesillo-Lazarte.

Abstract

In the title compound, [Ni(C(9)H(10)NO(2))(2)(H(2)O)(2)], the coordination geometry around the Ni(II) ion can be described as distorted octa-hedral, with two N atoms and two O atoms from phenyl-alaninate ligands in the basal plane and two aqua O atoms at the axial sites. The crystal packing is stabilized by inter-molecular O-H⋯O and N-H⋯O hydrogen bonds.

Entities: CellLine Chemical Disease Gene

Year: 2012 PMID： 22589818 PMCID： PMC3343844 DOI： 10.1107/S160053681201080X

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For background to amino acid complexes, see: Thanavelan et al. (2011 ▶). For related structures, see: Rombach et al. (2002 ▶); Marandi & Shahbakhsh (2007 ▶). For similar hydrogen-bonded networks, see: Cao et al. (2011 ▶). For details of π–π stacking interactions, see: Janiak (2000) ▶.

Experimental

Crystal data

[Ni(C9H10NO2)2(H2O)2] M = 423.10 Monoclinic, a = 4.8272 (5) Å b = 32.617 (4) Å c = 6.0585 (7) Å β = 105.995 (1)° V = 916.97 (18) Å3 Z = 2 Mo Kα radiation μ = 1.10 mm−1 T = 100 K 0.46 × 0.15 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2008 ▶) T min = 0.633, T max = 0.853 8826 measured reflections 3214 independent reflections 3157 reflections with I > 2σ(I) R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.023 wR(F 2) = 0.058 S = 1.06 3214 reflections 256 parameters 5 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.43 e Å−3 Δρmin = −0.22 e Å−3 Absolute structure: Flack (1983 ▶), 1567 Friedel pairs Flack parameter: −0.003 (10) Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: SAINT (Bruker, 2010 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶). Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681201080X/br2191sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681201080X/br2191Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ni(C₉H₁₀NO₂)₂(H₂O)₂]	F(000) = 444
M_r = 423.10	D_x = 1.532 Mg m⁻³
Monoclinic, P2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 7357 reflections
a = 4.8272 (5) Å	θ = 2.5–27.8°
b = 32.617 (4) Å	µ = 1.10 mm⁻¹
c = 6.0585 (7) Å	T = 100 K
β = 105.995 (1)°	Block, pale blue
V = 916.97 (18) Å³	0.46 × 0.15 × 0.15 mm
Z = 2

Bruker SMART APEX diffractometer	3214 independent reflections
Radiation source: fine-focus sealed tube	3157 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
φ and ω scans	θ_max = 25.0°, θ_min = 1.3°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −5→5
T_min = 0.633, T_max = 0.853	k = −38→38
8826 measured reflections	l = −7→7

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.023	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.058	w = 1/[σ²(F_o²) + (0.0344P)² + 0.0026P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
3214 reflections	Δρ_max = 0.43 e Å⁻³
256 parameters	Δρ_min = −0.22 e Å⁻³
5 restraints	Absolute structure: Flack (1983), 1567 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: −0.003 (10)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	U_iso*/U_eq
Ni1	0.28611 (5)	0.648490 (11)	0.40794 (4)	0.01552 (8)
O1	0.4353 (3)	0.62803 (5)	0.1433 (3)	0.0176 (3)
C2	0.3680 (5)	0.59137 (6)	0.0787 (4)	0.0154 (5)
O3	0.4153 (4)	0.57545 (5)	−0.0940 (3)	0.0208 (4)
C4	0.2425 (5)	0.56442 (7)	0.2377 (4)	0.0187 (5)
H4	0.4108	0.5512	0.3495	0.022*
N5	0.1012 (4)	0.59095 (5)	0.3755 (3)	0.0166 (4)
H5A	0.1239	0.5796	0.5184	0.020*
H5B	−0.0929	0.5929	0.3038	0.020*
C6	0.0588 (5)	0.52992 (7)	0.1089 (4)	0.0213 (5)
H6A	0.1709	0.5153	0.0189	0.026*
H6B	−0.1116	0.5421	−0.0019	0.026*
C7	−0.0470 (5)	0.49844 (7)	0.2534 (4)	0.0212 (5)
C8	−0.2788 (5)	0.47360 (8)	0.1455 (4)	0.0245 (5)
H8	−0.3693	0.4773	−0.0136	0.029*
C9	−0.3811 (6)	0.44351 (9)	0.2643 (5)	0.0285 (6)
H9	−0.5387	0.4268	0.1864	0.034*
C10	−0.2533 (6)	0.43785 (8)	0.4970 (5)	0.0262 (6)
H10	−0.3241	0.4175	0.5794	0.031*
C11	−0.0218 (6)	0.46217 (7)	0.6083 (4)	0.0249 (5)
H11	0.0675	0.4584	0.7675	0.030*
C12	0.0812 (5)	0.49241 (7)	0.4865 (4)	0.0233 (5)
H12	0.2402	0.5089	0.5640	0.028*
O13	−0.0828 (4)	0.67531 (5)	0.1807 (3)	0.0190 (3)
H13A	−0.231 (4)	0.6608 (7)	0.133 (4)	0.023*
H13B	−0.042 (6)	0.6837 (8)	0.059 (3)	0.023*
O21	0.1315 (3)	0.66878 (5)	0.6664 (3)	0.0173 (3)
C22	0.2192 (5)	0.70390 (7)	0.7484 (4)	0.0170 (5)
O23	0.1545 (4)	0.72004 (5)	0.9143 (3)	0.0215 (4)
C24	0.4021 (5)	0.72964 (7)	0.6278 (4)	0.0177 (5)
H24	0.5846	0.7379	0.7437	0.021*
N25	0.4761 (4)	0.70600 (5)	0.4425 (3)	0.0169 (4)
H25A	0.6730	0.7032	0.4760	0.020*
H25B	0.4138	0.7200	0.3060	0.020*
C26	0.2290 (5)	0.76835 (7)	0.5355 (4)	0.0218 (5)
H26A	0.0524	0.7601	0.4164	0.026*
H26B	0.1680	0.7813	0.6623	0.026*
C27	0.3862 (5)	0.80002 (7)	0.4338 (4)	0.0198 (5)
C28	0.6211 (5)	0.82146 (7)	0.5734 (4)	0.0220 (5)
H28	0.6866	0.8153	0.7326	0.026*
C29	0.7596 (6)	0.85182 (8)	0.4812 (5)	0.0255 (6)
H29	0.9187	0.8662	0.5773	0.031*
C30	0.6654 (6)	0.86095 (8)	0.2499 (5)	0.0274 (7)
H30	0.7605	0.8815	0.1868	0.033*
C31	0.4317 (6)	0.84014 (8)	0.1094 (4)	0.0278 (6)
H31	0.3651	0.8467	−0.0492	0.033*
C32	0.2955 (5)	0.80967 (7)	0.2019 (4)	0.0239 (5)
H32	0.1377	0.7952	0.1046	0.029*
O33	0.6519 (4)	0.62138 (5)	0.6364 (3)	0.0187 (3)
H33A	0.592 (6)	0.6108 (8)	0.740 (4)	0.022*
H33B	0.792 (4)	0.6368 (6)	0.684 (4)	0.022*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.01495 (13)	0.01567 (13)	0.01611 (13)	−0.00181 (13)	0.00456 (9)	0.00010 (13)
O1	0.0157 (8)	0.0181 (8)	0.0192 (8)	−0.0020 (6)	0.0051 (6)	0.0016 (7)
C2	0.0127 (11)	0.0169 (12)	0.0149 (12)	0.0017 (9)	0.0011 (9)	0.0025 (9)
O3	0.0238 (9)	0.0194 (8)	0.0224 (9)	−0.0007 (7)	0.0120 (7)	0.0004 (7)
C4	0.0191 (12)	0.0182 (12)	0.0197 (12)	−0.0010 (9)	0.0067 (10)	−0.0008 (9)
N5	0.0181 (10)	0.0161 (10)	0.0156 (9)	−0.0020 (8)	0.0044 (8)	−0.0015 (7)
C6	0.0250 (13)	0.0195 (12)	0.0186 (12)	−0.0010 (10)	0.0048 (10)	−0.0007 (9)
C7	0.0235 (13)	0.0177 (12)	0.0253 (13)	0.0015 (10)	0.0118 (10)	−0.0026 (9)
C8	0.0250 (13)	0.0251 (13)	0.0228 (13)	0.0014 (10)	0.0054 (10)	−0.0018 (10)
C9	0.0239 (15)	0.0243 (14)	0.0378 (16)	−0.0079 (11)	0.0092 (12)	−0.0063 (12)
C10	0.0332 (16)	0.0180 (13)	0.0329 (15)	−0.0034 (11)	0.0184 (13)	−0.0009 (11)
C11	0.0310 (14)	0.0197 (12)	0.0251 (13)	0.0021 (11)	0.0098 (11)	0.0016 (10)
C12	0.0234 (13)	0.0182 (12)	0.0279 (13)	−0.0034 (10)	0.0065 (11)	−0.0037 (10)
O13	0.0169 (8)	0.0235 (9)	0.0168 (9)	−0.0037 (7)	0.0051 (7)	0.0035 (7)
O21	0.0198 (8)	0.0170 (8)	0.0162 (8)	−0.0034 (7)	0.0069 (7)	−0.0011 (6)
C22	0.0131 (11)	0.0197 (12)	0.0174 (12)	0.0010 (9)	0.0030 (9)	0.0026 (9)
O23	0.0298 (10)	0.0194 (9)	0.0180 (9)	−0.0024 (7)	0.0111 (7)	0.0001 (7)
C24	0.0178 (12)	0.0155 (11)	0.0207 (12)	−0.0008 (9)	0.0068 (10)	−0.0002 (9)
N25	0.0171 (10)	0.0159 (10)	0.0184 (10)	−0.0017 (8)	0.0064 (8)	−0.0004 (7)
C26	0.0200 (12)	0.0211 (12)	0.0260 (12)	0.0023 (10)	0.0093 (10)	0.0026 (10)
C27	0.0215 (12)	0.0148 (11)	0.0253 (13)	0.0037 (10)	0.0101 (10)	−0.0005 (9)
C28	0.0233 (12)	0.0212 (12)	0.0221 (12)	0.0036 (10)	0.0076 (10)	0.0026 (9)
C29	0.0227 (14)	0.0170 (13)	0.0383 (16)	0.0007 (11)	0.0108 (12)	0.0000 (12)
C30	0.0340 (16)	0.0176 (13)	0.0367 (17)	0.0022 (11)	0.0200 (13)	0.0041 (11)
C31	0.0401 (16)	0.0232 (13)	0.0238 (13)	0.0040 (11)	0.0153 (12)	0.0032 (10)
C32	0.0292 (13)	0.0198 (12)	0.0236 (13)	0.0010 (10)	0.0086 (11)	0.0000 (10)
O33	0.0164 (8)	0.0219 (9)	0.0175 (8)	−0.0040 (7)	0.0042 (7)	0.0027 (6)

Ni1—O21	2.0223 (16)	C12—H12	0.9500
Ni1—O1	2.0421 (16)	O13—H13A	0.839 (17)
Ni1—N5	2.0642 (18)	O13—H13B	0.861 (17)
Ni1—N25	2.0731 (18)	O21—C22	1.274 (3)
Ni1—O33	2.1139 (17)	C22—O23	1.249 (3)
Ni1—O13	2.1171 (17)	C22—C24	1.541 (3)
O1—C2	1.272 (3)	C24—N25	1.484 (3)
C2—O3	1.245 (3)	C24—C26	1.532 (3)
C2—C4	1.546 (3)	C24—H24	1.0000
C4—N5	1.492 (3)	N25—H25A	0.9200
C4—C6	1.510 (3)	N25—H25B	0.9200
C4—H4	1.0000	C26—C27	1.510 (3)
N5—H5A	0.9200	C26—H26A	0.9900
N5—H5B	0.9200	C26—H26B	0.9900
C6—C7	1.526 (3)	C27—C32	1.388 (3)
C6—H6A	0.9900	C27—C28	1.401 (3)
C6—H6B	0.9900	C28—C29	1.395 (4)
C7—C8	1.390 (3)	C28—H28	0.9500
C7—C12	1.391 (3)	C29—C30	1.381 (4)
C8—C9	1.386 (4)	C29—H29	0.9500
C8—H8	0.9500	C30—C31	1.389 (4)
C9—C10	1.386 (4)	C30—H30	0.9500
C9—H9	0.9500	C31—C32	1.392 (3)
C10—C11	1.385 (4)	C31—H31	0.9500
C10—H10	0.9500	C32—H32	0.9500
C11—C12	1.402 (3)	O33—H33A	0.833 (17)
C11—H11	0.9500	O33—H33B	0.829 (17)

O21—Ni1—O1	179.03 (7)	C12—C11—H11	119.9
O21—Ni1—N5	97.42 (7)	C7—C12—C11	120.7 (2)
O1—Ni1—N5	82.24 (7)	C7—C12—H12	119.6
O21—Ni1—N25	82.71 (7)	C11—C12—H12	119.6
O1—Ni1—N25	97.64 (7)	Ni1—O13—H13A	118.2 (18)
N5—Ni1—N25	179.38 (8)	Ni1—O13—H13B	109.7 (18)
O21—Ni1—O33	92.85 (6)	H13A—O13—H13B	105 (2)
O1—Ni1—O33	88.04 (7)	C22—O21—Ni1	116.26 (14)
N5—Ni1—O33	86.75 (7)	O23—C22—O21	124.3 (2)
N25—Ni1—O33	92.64 (7)	O23—C22—C24	117.1 (2)
O21—Ni1—O13	86.82 (6)	O21—C22—C24	118.5 (2)
O1—Ni1—O13	92.29 (6)	N25—C24—C26	111.88 (18)
N5—Ni1—O13	92.84 (7)	N25—C24—C22	111.37 (18)
N25—Ni1—O13	87.77 (7)	C26—C24—C22	107.21 (18)
O33—Ni1—O13	179.43 (7)	N25—C24—H24	108.8
C2—O1—Ni1	115.66 (14)	C26—C24—H24	108.8
O3—C2—O1	124.1 (2)	C22—C24—H24	108.8
O3—C2—C4	118.74 (19)	C24—N25—Ni1	110.76 (14)
O1—C2—C4	116.99 (19)	C24—N25—H25A	109.5
N5—C4—C6	115.3 (2)	Ni1—N25—H25A	109.5
N5—C4—C2	109.68 (17)	C24—N25—H25B	109.5
C6—C4—C2	112.15 (19)	Ni1—N25—H25B	109.5
N5—C4—H4	106.4	H25A—N25—H25B	108.1
C6—C4—H4	106.4	C27—C26—C24	115.33 (19)
C2—C4—H4	106.4	C27—C26—H26A	108.4
C4—N5—Ni1	109.17 (14)	C24—C26—H26A	108.4
C4—N5—H5A	109.8	C27—C26—H26B	108.4
Ni1—N5—H5A	109.8	C24—C26—H26B	108.4
C4—N5—H5B	109.8	H26A—C26—H26B	107.5
Ni1—N5—H5B	109.8	C32—C27—C28	118.4 (2)
H5A—N5—H5B	108.3	C32—C27—C26	121.0 (2)
C4—C6—C7	116.5 (2)	C28—C27—C26	120.6 (2)
C4—C6—H6A	108.2	C29—C28—C27	120.7 (2)
C7—C6—H6A	108.2	C29—C28—H28	119.7
C4—C6—H6B	108.2	C27—C28—H28	119.7
C7—C6—H6B	108.2	C30—C29—C28	119.9 (3)
H6A—C6—H6B	107.3	C30—C29—H29	120.0
C8—C7—C12	118.1 (2)	C28—C29—H29	120.0
C8—C7—C6	118.4 (2)	C29—C30—C31	120.1 (2)
C12—C7—C6	123.5 (2)	C29—C30—H30	120.0
C9—C8—C7	121.6 (2)	C31—C30—H30	120.0
C9—C8—H8	119.2	C30—C31—C32	119.8 (2)
C7—C8—H8	119.2	C30—C31—H31	120.1
C8—C9—C10	120.0 (3)	C32—C31—H31	120.1
C8—C9—H9	120.0	C27—C32—C31	121.2 (2)
C10—C9—H9	120.0	C27—C32—H32	119.4
C11—C10—C9	119.5 (2)	C31—C32—H32	119.4
C11—C10—H10	120.3	Ni1—O33—H33A	105.4 (19)
C9—C10—H10	120.3	Ni1—O33—H33B	115.5 (17)
C10—C11—C12	120.1 (2)	H33A—O33—H33B	114 (3)
C10—C11—H11	119.9

D—H···A	D—H	H···A	D···A	D—H···A
O13—H13A···O1ⁱ	0.84 (2)	1.95 (2)	2.747 (2)	159 (2)
O13—H13B···O23ⁱⁱ	0.86 (2)	1.88 (2)	2.658 (2)	150 (3)
O33—H33A···O3ⁱⁱⁱ	0.83 (2)	1.88 (2)	2.691 (2)	163 (3)
O33—H33B···O21^iv	0.83 (2)	1.97 (2)	2.748 (2)	156 (2)
N5—H5B···O1ⁱ	0.92	2.49	3.359 (2)	157
N5—H5A···O3ⁱⁱⁱ	0.92	2.39	3.193 (3)	147
N25—H25A···O13^iv	0.92	2.57	3.148 (2)	122
N25—H25A···O21^iv	0.92	2.47	3.310 (2)	153
N25—H25B···O23ⁱⁱ	0.92	2.36	3.181 (3)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O13—H13A⋯O1ⁱ	0.84 (2)	1.95 (2)	2.747 (2)	159 (2)
O13—H13B⋯O23ⁱⁱ	0.86 (2)	1.88 (2)	2.658 (2)	150 (3)
O33—H33A⋯O3ⁱⁱⁱ	0.83 (2)	1.88 (2)	2.691 (2)	163 (3)
O33—H33B⋯O21^iv	0.83 (2)	1.97 (2)	2.748 (2)	156 (2)
N5—H5B⋯O1ⁱ	0.92	2.49	3.359 (2)	157
N5—H5A⋯O3ⁱⁱⁱ	0.92	2.39	3.193 (3)	147
N25—H25A⋯O13^iv	0.92	2.57	3.148 (2)	122
N25—H25A⋯O21^iv	0.92	2.47	3.310 (2)	153
N25—H25B⋯O23ⁱⁱ	0.92	2.36	3.181 (3)	149

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .

1 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

1 in total

1. Synthesis and characterisation of κ²-N,O-oxazoline-enolate complexes of nickel(ii): explorations in coordination chemistry and metal-mediated polymerisation.

Authors: Jeanette A Adjei; Alan J Lough; Robert A Gossage
Journal: RSC Adv Date: 2019-01-29 Impact factor: 4.036

1 in total

trans-Diaqua-bis-(l-phenyl-alaninato-κ(2)N,O)nickel(II).

Related literature

Experimental

Crystal data

Data collection

Refinement

1. A short history of SHELX.

1. Synthesis and characterisation of κ2-N,O-oxazoline-enolate complexes of nickel(ii): explorations in coordination chemistry and metal-mediated polymerisation.

1. Synthesis and characterisation of κ²-N,O-oxazoline-enolate complexes of nickel(ii): explorations in coordination chemistry and metal-mediated polymerisation.