(2-Amino-pyrimidine-κN)diaqua(pyridine-2,6-dicarboxyl-ato-κO,N,O)-nickel(II) monohydrate.

The reaction of Ni(NO(3))(2)·6H(2)O with pyridine-2,6-dicarboxylic acid, NaOH and 2-amino-pyrimidine in aqueous solution leads to the formation of the title complex, [Ni(C(7)H(3)NO(4))(C(4)H(5)N(3))(H(2)O)(2)]·H(2)O. The Ni(II) ion is coordinated by one N and two O atoms of the tridentate chelating pyridine-2,6-dicarboxyl-ate anion, one heterocyclic N atom of the 2-amino-pyrimidine ligand, and two water mol-ecules. The resulting geometry for the [NiN(2)O(4)] coordination environment can be described as distorted octa-hedral. One uncoord-inated water mol-ecule completes the asymmetric unit. Extensive O-H⋯O and N-H⋯O hydrogen-bonding inter-actions between the NH(2) group of 2-amino-pyrimidine, carboxyl-ate groups, and coordinated and uncoordinated water mol-ecules contribute to the formation of a three-dimensional supra-molecular structure.

Related literature

For transition metal complexes with 2-amino­pyrimidine, see: Ponticelli et al. (1999 ▶); Prince et al. (2003 ▶); Lee et al. (2003 ▶); Masaki et al. (2002 ▶). For related structures, see: Tabatabaee et al. (2008 ▶); Tabatabaee, Aghabozorg et al. (2009 ▶); Tabatabaee, Masoodpour et al. (2009 ▶); Tabatabaee, Sharif et al. (2009 ▶); Altin et al. (2004 ▶); Aghabozorg et al. (2007 ▶, 2008 ▶); Li et al. (2007 ▶).

Experimental

Crystal data

[Ni(C7H3NO4)(C4H5N3)(H2O)2]·H2O

M = 372.97

Monoclinic,

a = 9.6073 (8) Å

b = 10.2038 (10) Å

c = 14.6095 (15) Å

β = 102.677 (2)°

V = 1397.3 (2) Å3

Z = 4

Mo Kα radiation

μ = 1.44 mm−1

T = 120 K

0.24 × 0.22 × 0.15 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 1998 ▶) T min = 0.717, T max = 0.810

12010 measured reflections

2725 independent reflections

2396 reflections with I > 2σ(I)

R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.056

wR(F 2) = 0.163

S = 1.01

2725 reflections

208 parameters

H-atom parameters constrained

Δρmax = 0.65 e Å−3

Δρmin = −0.51 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT-Plus (Bruker, 1998 ▶); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810016843/bh2281sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810016843/bh2281Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ni(C7H3NO4)(C4H5N3)(H2O)2]·H2O	F(000) = 768
Mr = 372.97	Dx = 1.773 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 896 reflections
a = 9.6073 (8) Å	θ = 2.9–25.0°
b = 10.2038 (10) Å	µ = 1.44 mm−1
c = 14.6095 (15) Å	T = 120 K
β = 102.677 (2)°	Prism, blue
V = 1397.3 (2) Å3	0.24 × 0.22 × 0.15 mm
Z = 4

Bruker SMART 1000 CCD area-detector diffractometer	2725 independent reflections
Radiation source: fine-focus sealed tube	2396 reflections with I > 2σ(I)
graphite	Rint = 0.029
φ and ω scans	θmax = 26.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −11→11
Tmin = 0.717, Tmax = 0.810	k = −12→12
12010 measured reflections	l = −18→17

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)] = 0.056	Hydrogen site location: mixed
wR(F2) = 0.163	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.07P)2 + 9.P] where P = (Fo2 + 2Fc2)/3
2725 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.65 e Å−3
0 restraints	Δρmin = −0.51 e Å−3
0 constraints

	x	y	z	Uiso*/Ueq
Ni1	0.71391 (7)	0.20931 (6)	0.07096 (4)	0.0268 (2)
N1	0.7944 (4)	0.0931 (3)	0.1775 (2)	0.0212 (8)
N2	0.6262 (5)	0.3303 (4)	−0.0398 (3)	0.0364 (11)
N3	0.5712 (6)	0.5362 (6)	−0.1177 (3)	0.0574 (17)
N4	0.7236 (6)	0.5244 (4)	0.0275 (3)	0.0451 (13)
H4B	0.7678	0.4812	0.0758	0.054*
H4C	0.7332	0.6080	0.0254	0.054*
O1	0.7779 (4)	0.3446 (3)	0.1821 (2)	0.0328 (8)
O2	0.8528 (5)	0.3529 (3)	0.3379 (2)	0.0395 (9)
O3	0.6800 (4)	0.0198 (4)	0.0080 (2)	0.0328 (8)
O4	0.7485 (7)	−0.1853 (4)	0.0367 (3)	0.0740 (18)
C1	0.8233 (6)	0.2929 (4)	0.2627 (3)	0.0289 (11)
C2	0.8404 (5)	0.1458 (4)	0.2621 (3)	0.0229 (9)
C3	0.8944 (5)	0.0683 (5)	0.3388 (3)	0.0290 (10)
H3A	0.9272	0.1048	0.3979	0.035*
C4	0.8982 (6)	−0.0660 (5)	0.3249 (4)	0.0376 (12)
H4A	0.9347	−0.1210	0.3753	0.045*
C5	0.8481 (7)	−0.1188 (5)	0.2367 (4)	0.0394 (13)
H5A	0.8490	−0.2088	0.2272	0.047*
C6	0.7967 (5)	−0.0346 (4)	0.1630 (3)	0.0271 (10)
C7	0.7374 (5)	−0.0716 (5)	0.0620 (3)	0.0307 (11)
C8	0.6402 (7)	0.4615 (6)	−0.0441 (3)	0.0416 (15)
C9	0.5438 (7)	0.2718 (7)	−0.1134 (4)	0.0497 (17)
H9A	0.5343	0.1812	−0.1121	0.060*
C10	0.4716 (7)	0.3385 (8)	−0.1914 (4)	0.060 (2)
H10A	0.4143	0.2962	−0.2424	0.072*
C11	0.4907 (8)	0.4728 (8)	−0.1885 (4)	0.068 (3)
H11A	0.4436	0.5216	−0.2397	0.082*
O1W	0.5159 (4)	0.2003 (4)	0.1048 (2)	0.0419 (10)
H1	0.4722	0.1549	0.0585	0.063*
H2	0.4721	0.2693	0.1148	0.063*
O2W	0.9039 (4)	0.2190 (3)	0.0257 (2)	0.0266 (7)
H3	0.8894	0.1987	−0.0320	0.040*
H4	0.9753	0.1835	0.0619	0.040*
O3W	0.1432 (4)	0.1177 (3)	0.1323 (2)	0.0320 (8)
H5	0.1465	0.0351	0.1402	0.048*
H6	0.1922	0.1248	0.0907	0.048*

	U11	U22	U33	U12	U13	U23
Ni1	0.0394 (4)	0.0241 (3)	0.0137 (3)	0.0101 (3)	−0.0012 (2)	−0.0018 (2)
N1	0.0236 (19)	0.0191 (18)	0.0180 (17)	0.0013 (14)	−0.0016 (14)	−0.0012 (14)
N2	0.057 (3)	0.038 (2)	0.0124 (18)	0.029 (2)	0.0047 (18)	−0.0002 (16)
N3	0.080 (4)	0.071 (4)	0.028 (3)	0.056 (3)	0.028 (3)	0.027 (3)
N4	0.087 (4)	0.024 (2)	0.029 (2)	0.020 (2)	0.023 (2)	0.0073 (18)
O1	0.062 (2)	0.0211 (16)	0.0139 (15)	0.0066 (16)	0.0060 (15)	0.0004 (13)
O2	0.081 (3)	0.0207 (17)	0.0148 (16)	−0.0061 (17)	0.0053 (16)	−0.0018 (13)
O3	0.0317 (18)	0.041 (2)	0.0225 (16)	0.0007 (15)	0.0000 (14)	−0.0072 (15)
O4	0.174 (6)	0.021 (2)	0.031 (2)	−0.021 (3)	0.029 (3)	−0.0078 (17)
C1	0.048 (3)	0.017 (2)	0.019 (2)	−0.004 (2)	0.001 (2)	0.0006 (17)
C2	0.028 (2)	0.019 (2)	0.020 (2)	−0.0006 (17)	0.0011 (17)	−0.0022 (17)
C3	0.040 (3)	0.027 (2)	0.017 (2)	0.003 (2)	0.0000 (19)	0.0004 (18)
C4	0.060 (4)	0.024 (2)	0.028 (3)	0.013 (2)	0.009 (2)	0.010 (2)
C5	0.071 (4)	0.020 (2)	0.031 (3)	0.003 (2)	0.018 (3)	0.000 (2)
C6	0.036 (3)	0.019 (2)	0.027 (2)	−0.0036 (19)	0.0095 (19)	−0.0023 (18)
C7	0.038 (3)	0.028 (2)	0.029 (2)	−0.013 (2)	0.014 (2)	−0.007 (2)
C8	0.067 (4)	0.043 (3)	0.020 (2)	0.038 (3)	0.020 (2)	0.012 (2)
C9	0.059 (4)	0.066 (4)	0.019 (2)	0.039 (3)	−0.002 (2)	−0.007 (2)
C10	0.052 (4)	0.111 (6)	0.017 (2)	0.056 (4)	0.005 (2)	−0.002 (3)
C11	0.082 (5)	0.107 (6)	0.021 (3)	0.077 (5)	0.023 (3)	0.025 (3)
O1W	0.041 (2)	0.067 (3)	0.0181 (16)	0.0300 (19)	0.0075 (15)	0.0021 (16)
O2W	0.043 (2)	0.0210 (16)	0.0131 (14)	0.0062 (14)	−0.0003 (13)	−0.0016 (12)
O3W	0.047 (2)	0.0229 (17)	0.0244 (16)	0.0005 (15)	0.0040 (15)	0.0003 (13)

Ni1—N1	1.975 (4)	C2—C3	1.377 (6)
Ni1—N2	2.062 (4)	C3—C4	1.388 (7)
Ni1—O1W	2.070 (4)	C3—H3A	0.9300
Ni1—O2W	2.076 (4)	C4—C5	1.382 (7)
Ni1—O1	2.117 (3)	C4—H4A	0.9300
Ni1—O3	2.136 (4)	C5—C6	1.381 (7)
N1—C6	1.321 (6)	C5—H5A	0.9300
N1—C2	1.330 (5)	C6—C7	1.509 (6)
N2—C9	1.329 (7)	C9—C10	1.377 (8)
N2—C8	1.348 (8)	C9—H9A	0.9300
N3—C11	1.317 (10)	C10—C11	1.382 (12)
N3—C8	1.365 (6)	C10—H10A	0.9300
N4—C8	1.334 (8)	C11—H11A	0.9300
N4—H4B	0.8600	O1W—H1	0.8500
N4—H4C	0.8600	O1W—H2	0.8499
O1—C1	1.278 (5)	O2W—H3	0.8500
O2—C1	1.235 (6)	O2W—H4	0.8500
O3—C7	1.267 (6)	O3W—H5	0.8500
O4—C7	1.230 (6)	O3W—H6	0.8500
C1—C2	1.510 (6)
N1—Ni1—N2	178.94 (18)	C2—C3—H3A	121.1
N1—Ni1—O1W	90.35 (15)	C4—C3—H3A	121.1
N2—Ni1—O1W	88.59 (17)	C5—C4—C3	120.4 (5)
N1—Ni1—O2W	93.46 (14)	C5—C4—H4A	119.8
N2—Ni1—O2W	87.59 (16)	C3—C4—H4A	119.8
O1W—Ni1—O2W	175.37 (12)	C6—C5—C4	118.5 (5)
N1—Ni1—O1	77.84 (13)	C6—C5—H5A	120.8
N2—Ni1—O1	102.19 (15)	C4—C5—H5A	120.8
O1W—Ni1—O1	88.48 (15)	N1—C6—C5	120.2 (4)
O2W—Ni1—O1	94.88 (13)	N1—C6—C7	112.9 (4)
N1—Ni1—O3	78.02 (13)	C5—C6—C7	126.9 (4)
N2—Ni1—O3	101.92 (15)	O4—C7—O3	124.2 (5)
O1W—Ni1—O3	90.07 (15)	O4—C7—C6	119.4 (5)
O2W—Ni1—O3	88.15 (13)	O3—C7—C6	116.4 (4)
O1—Ni1—O3	155.80 (13)	N4—C8—N2	119.3 (4)
C6—N1—C2	122.3 (4)	N4—C8—N3	117.0 (6)
C6—N1—Ni1	118.9 (3)	N2—C8—N3	123.7 (6)
C2—N1—Ni1	118.8 (3)	N2—C9—C10	123.4 (7)
C9—N2—C8	117.1 (5)	N2—C9—H9A	118.3
C9—N2—Ni1	115.7 (4)	C10—C9—H9A	118.3
C8—N2—Ni1	127.1 (4)	C9—C10—C11	115.1 (6)
C11—N3—C8	116.4 (6)	C9—C10—H10A	122.4
C8—N4—H4B	120.0	C11—C10—H10A	122.4
C8—N4—H4C	120.0	N3—C11—C10	124.2 (5)
H4B—N4—H4C	120.0	N3—C11—H11A	117.9
C1—O1—Ni1	114.9 (3)	C10—C11—H11A	117.9
C7—O3—Ni1	113.2 (3)	Ni1—O1W—H1	98.9
O2—C1—O1	125.5 (4)	Ni1—O1W—H2	121.3
O2—C1—C2	119.6 (4)	H1—O1W—H2	114.3
O1—C1—C2	114.8 (4)	Ni1—O2W—H3	109.9
N1—C2—C3	120.9 (4)	Ni1—O2W—H4	115.4
N1—C2—C1	113.2 (4)	H3—O2W—H4	116.5
C3—C2—C1	126.0 (4)	H5—O3W—H6	99.9
C2—C3—C4	117.7 (4)
O1W—Ni1—N1—C6	92.7 (4)	O2—C1—C2—N1	175.1 (5)
O2W—Ni1—N1—C6	−84.7 (4)	O1—C1—C2—N1	−5.0 (6)
O1—Ni1—N1—C6	−179.0 (4)	O2—C1—C2—C3	−3.6 (8)
O3—Ni1—N1—C6	2.7 (3)	O1—C1—C2—C3	176.3 (5)
O1W—Ni1—N1—C2	−85.3 (3)	N1—C2—C3—C4	−0.4 (7)
O2W—Ni1—N1—C2	97.3 (3)	C1—C2—C3—C4	178.2 (5)
O1—Ni1—N1—C2	3.0 (3)	C2—C3—C4—C5	−0.5 (8)
O3—Ni1—N1—C2	−175.3 (4)	C3—C4—C5—C6	1.1 (9)
O1W—Ni1—N2—C9	−75.1 (4)	C2—N1—C6—C5	0.0 (7)
O2W—Ni1—N2—C9	102.3 (4)	Ni1—N1—C6—C5	−177.9 (4)
O1—Ni1—N2—C9	−163.2 (4)	C2—N1—C6—C7	179.2 (4)
O3—Ni1—N2—C9	14.7 (4)	Ni1—N1—C6—C7	1.3 (5)
O1W—Ni1—N2—C8	102.8 (5)	C4—C5—C6—N1	−0.8 (8)
O2W—Ni1—N2—C8	−79.8 (5)	C4—C5—C6—C7	−179.9 (5)
O1—Ni1—N2—C8	14.7 (5)	Ni1—O3—C7—O4	−169.6 (5)
O3—Ni1—N2—C8	−167.4 (4)	Ni1—O3—C7—C6	9.5 (5)
N1—Ni1—O1—C1	−5.9 (4)	N1—C6—C7—O4	171.6 (5)
N2—Ni1—O1—C1	173.0 (4)	C5—C6—C7—O4	−9.3 (8)
O1W—Ni1—O1—C1	84.8 (4)	N1—C6—C7—O3	−7.5 (6)
O2W—Ni1—O1—C1	−98.4 (4)	C5—C6—C7—O3	171.6 (5)
O3—Ni1—O1—C1	−2.0 (6)	C9—N2—C8—N4	−179.0 (5)
N1—Ni1—O3—C7	−6.9 (3)	Ni1—N2—C8—N4	3.2 (7)
N2—Ni1—O3—C7	174.2 (3)	C9—N2—C8—N3	2.3 (8)
O1W—Ni1—O3—C7	−97.2 (3)	Ni1—N2—C8—N3	−175.6 (4)
O2W—Ni1—O3—C7	87.1 (3)	C11—N3—C8—N4	179.1 (5)
O1—Ni1—O3—C7	−10.7 (6)	C11—N3—C8—N2	−2.1 (8)
Ni1—O1—C1—O2	−172.6 (5)	C8—N2—C9—C10	−1.2 (9)
Ni1—O1—C1—C2	7.4 (6)	Ni1—N2—C9—C10	176.9 (5)
C6—N1—C2—C3	0.6 (7)	N2—C9—C10—C11	0.0 (9)
Ni1—N1—C2—C3	178.6 (4)	C8—N3—C11—C10	0.8 (9)
C6—N1—C2—C1	−178.1 (4)	C9—C10—C11—N3	0.2 (9)
Ni1—N1—C2—C1	−0.2 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N4—H4B···O1	0.86	2.07	2.867 (5)	153
N4—H4C···O4i	0.86	2.12	2.973 (6)	173
O1W—H1···O4ii	0.85	2.29	2.906 (7)	130
O1W—H1···O3ii	0.85	2.37	3.152 (5)	152
O1W—H2···N3iii	0.85	2.03	2.835 (7)	158
O2W—H3···O2iv	0.85	1.93	2.777 (4)	178
O2W—H4···O3Wv	0.85	1.84	2.685 (5)	173
O3W—H5···O2vi	0.85	1.89	2.736 (4)	177
O3W—H6···O4ii	0.85	2.15	2.964 (6)	159
O3W—H6···O3ii	0.85	2.56	3.253 (5)	140

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4—H4B⋯O1	0.86	2.07	2.867 (5)	153
N4—H4C⋯O4i	0.86	2.12	2.973 (6)	173
O1W—H1⋯O4ii	0.85	2.29	2.906 (7)	130
O1W—H1⋯O3ii	0.85	2.37	3.152 (5)	152
O2W—H3⋯O2iii	0.85	1.93	2.777 (4)	178
O2W—H4⋯O3Wiv	0.85	1.84	2.685 (5)	173
O3W—H5⋯O2v	0.85	1.89	2.736 (4)	177
O3W—H6⋯O4ii	0.85	2.15	2.964 (6)	159
O3W—H6⋯O3ii	0.85	2.56	3.253 (5)	140

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