Literature DB >> 22090834

Aqua-(4-carb-oxy-pyridine-2,6-dicarboxyl-ato-κO,N,O)(1,10-phenanthroline-κN,N')nickel(II).

Abstract

The title compound, [Ni(C(8)H(3)NO(6))(C(12)H(8)N(2))(H(2)O)], contains an Ni(II) ion, a 1,10-phenanthroline (phen) ligand, a 4-carb-oxy-pyridine-2,6-dicarboxyl-ate (Hptc(2-)) anion and a coordinated water mol-ecule. The Ni(II) atom exhibits a distorted octa-hedral N(3)O(3) environment. O-H⋯O hydrogen bonding between coordinated water and carboxyl-ate O atoms, as well as π-π stacking inter-actions [inter-planar distances between phen rings = 3.293 (2) Å] lead to a supermolecular assembly.

Entities: CellLine Chemical Disease Species

Year: 2011 PMID： 22090834 PMCID： PMC3212132 DOI： 10.1107/S1600536811026055

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

Related literature

For the synthesis of pyridine-2,4,6-tricarboxylic acid, see: Syper et al. (1980 ▶). For related structures, see: Ma et al. (2002 ▶); Ramadevi et al. (2006 ▶); Harrison et al. (2006 ▶).

Experimental

Crystal data

[Ni(C8H3NO6)(n class="CellLine">C12H8N2)(H2O)] M = 466.04 Monoclinic, a = 6.8387 (14) Å b = 13.421 (3) Å c = 19.676 (4) Å β = 91.87 (3)° V = 1805.0 (6) Å3 Z = 4 Mo Kα radiation μ = 1.13 mm−1 T = 293 K 0.24 × 0.22 × 0.10 mm

Data collection

Rigaku R-AXIS RAPID diffractometer Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.763, T max = 0.893 17250 measured reflections 4058 independent reflections 2573 reflections with I > 2σ(I) R int = 0.054

Refinement

R[F 2 > 2σ(F 2)] = 0.044 wR(F 2) = 0.142 S = 1.19 4058 reflections 280 parameters H-atom parameters constrained Δρmax = 1.34 e Å−3 Δρmin = −1.52 e Å−3 Data collection: RAPID-AUTO (Rigaku, 1998 ▶); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811026055/pv2419sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811026055/pv2419Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ni(C₈H₃NO₆)(C₁₂H₈N₂)(H₂O)]	F(000) = 952
M_r = 466.04	D_x = 1.715 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 10705 reflections
a = 6.8387 (14) Å	θ = 3.0–27.4°
b = 13.421 (3) Å	µ = 1.13 mm⁻¹
c = 19.676 (4) Å	T = 293 K
β = 91.87 (3)°	Chip, green
V = 1805.0 (6) Å³	0.24 × 0.22 × 0.10 mm
Z = 4

Rigaku R-AXIS RAPID diffractometer	4058 independent reflections
Radiation source: fine-focus sealed tube	2573 reflections with I > 2σ(I)
graphite	R_int = 0.054
Detector resolution: 0 pixels mm^-1	θ_max = 27.5°, θ_min = 3.0°
ω scan	h = −8→7
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	k = −17→17
T_min = 0.763, T_max = 0.893	l = −25→24
17250 measured reflections

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.142	H-atom parameters constrained
S = 1.19	w = 1/[σ²(F_o²) + (0.0123P)² + 8.1487P] where P = (F_o² + 2F_c²)/3
4058 reflections	(Δ/σ)_max < 0.001
280 parameters	Δρ_max = 1.34 e Å⁻³
0 restraints	Δρ_min = −1.52 e Å⁻³

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.

	x	y	z	U_iso*/U_eq
Ni1	0.26648 (9)	0.77711 (4)	0.53877 (3)	0.02863 (18)
N1	0.2227 (6)	0.8906 (3)	0.60244 (19)	0.0268 (9)
C1	0.3686 (7)	0.9196 (3)	0.6443 (2)	0.0309 (11)
C2	0.3585 (7)	1.0087 (3)	0.6793 (2)	0.0304 (11)
H2A	0.4603	1.0289	0.7086	0.036*
C3	0.1919 (7)	1.0673 (3)	0.6695 (2)	0.0286 (10)
C4	0.0397 (7)	1.0350 (3)	0.6258 (2)	0.0297 (10)
H4A	−0.0730	1.0730	0.6191	0.036*
C5	0.0617 (7)	0.9450 (3)	0.5930 (2)	0.0260 (10)
C6	0.5378 (7)	0.8459 (3)	0.6473 (2)	0.0291 (10)
O1	0.5323 (5)	0.7781 (3)	0.60344 (17)	0.0341 (8)
O2	0.6618 (5)	0.8555 (3)	0.69549 (19)	0.0418 (9)
C7	0.1719 (8)	1.1668 (4)	0.7044 (2)	0.0343 (11)
O3	0.3151 (6)	1.1847 (3)	0.7480 (2)	0.0595 (13)
H3A	0.3243	1.2410	0.7678	0.071*
O4	0.0343 (6)	1.2209 (3)	0.6934 (2)	0.0495 (10)
C8	−0.0789 (7)	0.9010 (3)	0.5395 (2)	0.0275 (10)
O5	−0.2403 (5)	0.9434 (2)	0.52867 (18)	0.0337 (8)
O6	−0.0182 (5)	0.8251 (2)	0.50894 (17)	0.0339 (8)
N2	0.2834 (6)	0.6679 (3)	0.4662 (2)	0.0322 (9)
C9	0.3157 (8)	0.6781 (4)	0.4005 (3)	0.0422 (13)
H9A	0.3303	0.7417	0.3828	0.051*
C10	0.3286 (9)	0.5957 (5)	0.3570 (3)	0.0497 (15)
H10A	0.3494	0.6053	0.3109	0.060*
C11	0.3106 (8)	0.5023 (5)	0.3821 (3)	0.0498 (16)
H11A	0.3230	0.4474	0.3537	0.060*
C12	0.2735 (7)	0.4888 (4)	0.4508 (3)	0.0404 (13)
C13	0.2495 (8)	0.3931 (4)	0.4819 (4)	0.0489 (16)
H13A	0.2571	0.3358	0.4556	0.059*
C14	0.2159 (8)	0.3851 (4)	0.5490 (4)	0.0494 (16)
H14A	0.2020	0.3223	0.5681	0.059*
C15	0.2011 (7)	0.4721 (4)	0.5916 (3)	0.0375 (12)
C16	0.1738 (8)	0.4681 (4)	0.6613 (3)	0.0463 (15)
H16A	0.1622	0.4071	0.6832	0.056*
C17	0.1642 (9)	0.5552 (5)	0.6972 (3)	0.0507 (15)
H17A	0.1518	0.5538	0.7441	0.061*
C18	0.1734 (8)	0.6465 (4)	0.6628 (3)	0.0422 (13)
H18A	0.1594	0.7050	0.6875	0.051*
C19	0.2191 (7)	0.5668 (4)	0.5611 (3)	0.0317 (11)
C20	0.2586 (7)	0.5750 (4)	0.4907 (3)	0.0324 (11)
N3	0.2010 (6)	0.6526 (3)	0.5969 (2)	0.0324 (9)
O7	0.4073 (5)	0.8742 (2)	0.47182 (17)	0.0345 (8)
H7A	0.3512	0.9298	0.4780	0.041*
H7B	0.5130	0.8761	0.4958	0.041*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0348 (3)	0.0194 (3)	0.0314 (3)	0.0007 (3)	−0.0033 (2)	−0.0022 (3)
N1	0.034 (2)	0.0173 (18)	0.028 (2)	0.0010 (16)	−0.0053 (17)	−0.0006 (15)
C1	0.040 (3)	0.020 (2)	0.033 (3)	0.001 (2)	−0.005 (2)	0.0031 (19)
C2	0.034 (3)	0.023 (2)	0.034 (3)	0.000 (2)	−0.008 (2)	−0.001 (2)
C3	0.036 (3)	0.021 (2)	0.028 (2)	−0.002 (2)	−0.002 (2)	−0.0005 (19)
C4	0.038 (3)	0.022 (2)	0.028 (2)	0.002 (2)	−0.005 (2)	0.0019 (19)
C5	0.030 (2)	0.020 (2)	0.028 (2)	0.0004 (18)	−0.0018 (19)	0.0029 (18)
C6	0.037 (3)	0.019 (2)	0.031 (3)	−0.0007 (19)	−0.007 (2)	0.0048 (19)
O1	0.0378 (19)	0.0238 (17)	0.040 (2)	0.0042 (15)	−0.0057 (15)	−0.0025 (15)
O2	0.049 (2)	0.0286 (19)	0.046 (2)	0.0032 (17)	−0.0203 (18)	0.0017 (16)
C7	0.047 (3)	0.025 (2)	0.030 (3)	−0.002 (2)	−0.005 (2)	−0.003 (2)
O3	0.068 (3)	0.039 (2)	0.069 (3)	0.011 (2)	−0.035 (2)	−0.028 (2)
O4	0.057 (3)	0.031 (2)	0.059 (3)	0.0141 (19)	−0.021 (2)	−0.0126 (19)
C8	0.036 (3)	0.021 (2)	0.025 (2)	−0.003 (2)	−0.003 (2)	0.0037 (18)
O5	0.0275 (18)	0.0263 (18)	0.047 (2)	0.0016 (15)	−0.0073 (15)	−0.0007 (15)
O6	0.038 (2)	0.0237 (17)	0.039 (2)	0.0017 (15)	−0.0099 (15)	−0.0071 (15)
N2	0.033 (2)	0.028 (2)	0.036 (2)	0.0024 (17)	−0.0039 (18)	−0.0058 (18)
C9	0.043 (3)	0.042 (3)	0.041 (3)	0.003 (3)	−0.001 (2)	−0.008 (3)
C10	0.052 (4)	0.058 (4)	0.038 (3)	0.008 (3)	−0.009 (3)	−0.014 (3)
C11	0.043 (3)	0.046 (4)	0.060 (4)	0.008 (3)	−0.008 (3)	−0.029 (3)
C12	0.028 (3)	0.033 (3)	0.060 (4)	0.005 (2)	−0.011 (2)	−0.015 (3)
C13	0.034 (3)	0.028 (3)	0.083 (5)	0.005 (2)	−0.011 (3)	−0.015 (3)
C14	0.038 (3)	0.020 (3)	0.090 (5)	0.000 (2)	−0.004 (3)	0.000 (3)
C15	0.026 (3)	0.030 (3)	0.057 (3)	0.001 (2)	−0.003 (2)	0.006 (2)
C16	0.033 (3)	0.035 (3)	0.070 (4)	−0.001 (2)	0.004 (3)	0.019 (3)
C17	0.050 (4)	0.052 (4)	0.050 (4)	0.001 (3)	0.005 (3)	0.018 (3)
C18	0.048 (3)	0.040 (3)	0.039 (3)	0.001 (3)	0.007 (2)	0.001 (2)
C19	0.026 (2)	0.025 (2)	0.044 (3)	−0.0004 (19)	−0.008 (2)	−0.003 (2)
C20	0.029 (3)	0.024 (2)	0.043 (3)	0.003 (2)	−0.010 (2)	−0.006 (2)
N3	0.040 (2)	0.024 (2)	0.034 (2)	−0.0017 (18)	−0.0001 (18)	0.0019 (17)
O7	0.039 (2)	0.0264 (18)	0.0378 (19)	0.0009 (15)	−0.0046 (15)	−0.0006 (15)

Ni1—N1	2.001 (4)	N2—C20	1.349 (6)
Ni1—N2	2.053 (4)	C9—C10	1.403 (8)
Ni1—N3	2.081 (4)	C9—H9A	0.9300
Ni1—O7	2.108 (4)	C10—C11	1.355 (9)
Ni1—O6	2.115 (3)	C10—H10A	0.9300
Ni1—O1	2.184 (3)	C11—C12	1.395 (8)
N1—C5	1.329 (6)	C11—H11A	0.9300
N1—C1	1.331 (6)	C12—C20	1.402 (7)
C1—C2	1.381 (6)	C12—C13	1.435 (8)
C1—C6	1.522 (7)	C13—C14	1.352 (9)
C2—C3	1.393 (7)	C13—H13A	0.9300
C2—H2A	0.9300	C14—C15	1.442 (8)
C3—C4	1.398 (6)	C14—H14A	0.9300
C3—C7	1.510 (7)	C15—C16	1.391 (8)
C4—C5	1.380 (6)	C15—C19	1.413 (7)
C4—H4A	0.9300	C16—C17	1.368 (9)
C5—C8	1.522 (6)	C16—H16A	0.9300
C6—O1	1.254 (6)	C17—C18	1.401 (8)
C6—O2	1.258 (6)	C17—H17A	0.9300
C7—O4	1.203 (6)	C18—N3	1.320 (6)
C7—O3	1.302 (6)	C18—H18A	0.9300
O3—H3A	0.8512	C19—N3	1.358 (6)
C8—O5	1.253 (6)	C19—C20	1.425 (7)
C8—O6	1.261 (6)	O7—H7A	0.8502
N2—C9	1.325 (7)	O7—H7B	0.8498

N1—Ni1—N2	172.90 (16)	C9—N2—C20	118.0 (4)
N1—Ni1—N3	103.18 (16)	C9—N2—Ni1	128.3 (4)
N2—Ni1—N3	80.03 (17)	C20—N2—Ni1	113.7 (3)
N1—Ni1—O7	90.09 (15)	N2—C9—C10	122.0 (6)
N2—Ni1—O7	88.24 (15)	N2—C9—H9A	119.0
N3—Ni1—O7	161.85 (15)	C10—C9—H9A	119.0
N1—Ni1—O6	77.69 (14)	C11—C10—C9	119.8 (6)
N2—Ni1—O6	95.55 (14)	C11—C10—H10A	120.1
N3—Ni1—O6	100.60 (16)	C9—C10—H10A	120.1
O7—Ni1—O6	94.23 (14)	C10—C11—C12	119.7 (5)
N1—Ni1—O1	76.68 (14)	C10—C11—H11A	120.2
N2—Ni1—O1	110.16 (15)	C12—C11—H11A	120.2
N3—Ni1—O1	82.81 (15)	C11—C12—C20	117.0 (5)
O7—Ni1—O1	88.39 (13)	C11—C12—C13	123.8 (5)
O6—Ni1—O1	154.24 (13)	C20—C12—C13	119.2 (5)
C5—N1—C1	121.8 (4)	C14—C13—C12	120.8 (5)
C5—N1—Ni1	118.1 (3)	C14—C13—H13A	119.6
C1—N1—Ni1	119.1 (3)	C12—C13—H13A	119.6
N1—C1—C2	120.8 (4)	C13—C14—C15	121.4 (5)
N1—C1—C6	112.8 (4)	C13—C14—H14A	119.3
C2—C1—C6	126.4 (4)	C15—C14—H14A	119.3
C1—C2—C3	118.3 (4)	C16—C15—C19	118.0 (5)
C1—C2—H2A	120.8	C16—C15—C14	123.8 (5)
C3—C2—H2A	120.8	C19—C15—C14	118.2 (5)
C2—C3—C4	119.9 (4)	C17—C16—C15	119.1 (5)
C2—C3—C7	121.6 (4)	C17—C16—H16A	120.5
C4—C3—C7	118.5 (4)	C15—C16—H16A	120.5
C5—C4—C3	118.0 (4)	C16—C17—C18	119.6 (6)
C5—C4—H4A	121.0	C16—C17—H17A	120.2
C3—C4—H4A	121.0	C18—C17—H17A	120.2
N1—C5—C4	121.2 (4)	N3—C18—C17	122.6 (5)
N1—C5—C8	112.7 (4)	N3—C18—H18A	118.7
C4—C5—C8	126.0 (4)	C17—C18—H18A	118.7
O1—C6—O2	126.7 (5)	N3—C19—C15	122.2 (5)
O1—C6—C1	116.1 (4)	N3—C19—C20	117.5 (4)
O2—C6—C1	117.1 (4)	C15—C19—C20	120.3 (5)
C6—O1—Ni1	114.3 (3)	N2—C20—C12	123.4 (5)
O4—C7—O3	125.1 (5)	N2—C20—C19	116.6 (4)
O4—C7—C3	122.3 (5)	C12—C20—C19	120.0 (5)
O3—C7—C3	112.6 (4)	C18—N3—C19	118.4 (5)
C7—O3—H3A	120.5	C18—N3—Ni1	129.1 (4)
O5—C8—O6	126.0 (4)	C19—N3—Ni1	111.8 (3)
O5—C8—C5	118.3 (4)	Ni1—O7—H7A	103.6
O6—C8—C5	115.7 (4)	Ni1—O7—H7B	94.0
C8—O6—Ni1	115.4 (3)	H7A—O7—H7B	105.9

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···O2ⁱ	0.85	1.70	2.550 (5)	178
O7—H7A···O5ⁱⁱ	0.85	1.87	2.702 (5)	167
O7—H7B···O5ⁱⁱⁱ	0.85	2.00	2.783 (5)	152

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯O2ⁱ	0.85	1.70	2.550 (5)	178
O7—H7A⋯O5ⁱⁱ	0.85	1.87	2.702 (5)	167
O7—H7B⋯O5ⁱⁱⁱ	0.85	2.00	2.783 (5)	152

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

2 in total

1. A short history of SHELX.

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

2. Aqua(dipicolinato-kappa 3 O2,N,O6)(1,10-phenanthroline-kappa 2N,N')manganese(II) monohydrate.

Authors: Chengbing Ma; Cheng Fan; Changneng Chen; Qiutian Liu
Journal: Acta Crystallogr C Date: 2002-10-31 Impact factor: 1.172

2 in total