Ammonium tris­(3-amino­pyrazine-2-carboxyl­ato-κ2N1,O)nickelate(II) trihydrate

Cheng, X.-L.; Gao, S.; Ng, S.W.

doi:10.1107/S1600536809048363

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Pages m1631-m1632

doi:10.1107/S1600536809048363

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Ammonium tris(3-aminopyrazine-2-carboxylato-κ²N¹,O)nickelate(II) trihydrate

Xiao-Li Cheng,^a Shan Gao ^a and Seik Weng Ng ^b ^*

^aCollege of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 14 November 2009; accepted 14 November 2009; online 21 November 2009)

The Ni^II atom in the title hydrated salt, (NH₄)[Ni(C₅H₄N₃O₂)₃]·3H₂O, is N,O-chelated by the three 3-aminopyrazine-2-carboxylate ligands, resulting in a distorted octahedral mer-NiN₃O₃ geometry for the metal. In the crystal, the complex anion, ammonium cation and uncoordinated water molecules are linked by extensive N—H⋯N, N—H⋯O, O—H⋯N and O—H⋯O hydrogen bonds, forming a three-dimensional network.

Related literature

For the crystal structure of diaquabis(3-aminopyrazine-2-carboxylato)nickel(II), see: Ptasiewicz-Bak & Leciejewicz (1999 ).

Experimental

Crystal data

(NH₄)[Ni(C₅H₄N₃O₂)₃]·3H₂O
M_r = 545.14
Monoclinic, P 2₁ /n
a = 11.2092 (3) Å
b = 14.7061 (4) Å
c = 13.7540 (4) Å
β = 97.5214 (8)°
V = 2247.75 (11) Å³
Z = 4
Mo Kα radiation
μ = 0.93 mm⁻¹
T = 293 K
0.28 × 0.22 × 0.19 mm

Data collection

Rigaku R-AXIS RAPID IP diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.780, T_max = 0.843
21341 measured reflections
5114 independent reflections
4322 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.096
S = 1.02
5114 reflections
380 parameters
25 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.26 e Å⁻³

Table 1
Selected bond lengths (Å)

Ni1—O1	2.0476 (13)
Ni1—O3	2.0526 (13)
Ni1—O5	2.0567 (13)
Ni1—N7	2.0561 (14)
Ni1—N4	2.0805 (14)
Ni1—N1	2.0857 (15)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H31⋯O2	0.85 (1)	2.08 (2)	2.740 (3)	134 (2)
N6—H61⋯O4	0.85 (1)	2.01 (2)	2.701 (3)	138 (2)
N6—H62⋯N5ⁱ	0.85 (1)	2.15 (1)	2.992 (2)	175 (2)
N9—H91⋯O6	0.86 (1)	2.07 (2)	2.733 (2)	134 (2)
N9—H92⋯O3ⁱⁱ	0.85 (1)	2.10 (1)	2.924 (2)	164 (2)
N10—H101⋯O2	0.86 (1)	1.91 (1)	2.756 (3)	169 (3)
N10—H102⋯O1w	0.86 (1)	1.94 (1)	2.779 (3)	164 (3)
N10—H103⋯O2w	0.85 (1)	2.07 (1)	2.919 (3)	172 (3)
N10—H104⋯N8ⁱⁱⁱ	0.84 (1)	2.36 (2)	3.018 (3)	135 (2)
O1w—H1w1⋯O1	0.84 (1)	2.25 (2)	2.964 (3)	143 (4)
O1w—H1w2⋯N2^iv	0.85 (1)	2.00 (1)	2.842 (3)	171 (4)
O2w—H2w1⋯O5^v	0.85 (1)	2.03 (1)	2.869 (2)	168 (3)
O2w—H2w2⋯O6^vi	0.84 (1)	1.96 (1)	2.766 (2)	159 (3)
O3w—H3w1⋯O4	0.85 (1)	2.39 (5)	2.812 (3)	111 (4)
Symmetry codes: (i) -x, -y+2, -z+1; (ii) -x+1, -y+1, -z+1; (iii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (v) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (vi) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO data reduction: CrystalClear (Rigaku/MSC, 2002 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809048363/hb5228sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809048363/hb5228Isup2.hkl

checkCIF report

Related literature top

For the crystal structure of diaquabis(3-aminopyrazine-2-carboxylato)nickel(II), see: Ptasiewicz-Bak & Leciejewicz (1999).

Experimental top

Nickel dichloride hexahydrate (0.48 g, 2 mmol), 3-aminopyrazine-2-carboxylic acid (0.56 g, 4 mmol) and sodium hydroxide (0.16 g 4 mmol) were dissolved in a water/DMF (v/v = 10 ml:1 ml) mixture. The solution was sealed in a 50 ml Teflon-lined stainless steel bomb and held at 443 K for 3 days. The bomb was gradually cooled to room temperature;, and green blocks of (I) were obtained after several days. The presence of the ammonium counterion is explained by the decomposition of DMF.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: CrystalClear (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2009).

Figures top

Fig. 1. The molecular structure of (I) at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius.

Ammonium tris(3-aminopyrazine-2-carboxylato-κ²N¹,O)nickelate(II) trihydrate top

Crystal data top

(NH₄)[Ni(C₅H₄N₃O₂)₃]·3H₂O	F(000) = 1128
M_r = 545.14	D_x = 1.611 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 17239 reflections
a = 11.2092 (3) Å	θ = 3.2–27.5°
b = 14.7061 (4) Å	µ = 0.93 mm⁻¹
c = 13.7540 (4) Å	T = 293 K
β = 97.5214 (8)°	Block, green
V = 2247.75 (11) Å³	0.28 × 0.22 × 0.19 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	5114 independent reflections
Radiation source: fine-focus sealed tube	4322 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
ω scan	θ_max = 27.4°, θ_min = 3.2°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −14→14
T_min = 0.780, T_max = 0.843	k = −19→19
21341 measured reflections	l = −17→17

Refinement top

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)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0582P)² + 0.5222P] where P = (F_o² + 2F_c²)/3
5114 reflections	(Δ/σ)_max = 0.001
380 parameters	Δρ_max = 0.47 e Å⁻³
25 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

(NH₄)[Ni(C₅H₄N₃O₂)₃]·3H₂O	V = 2247.75 (11) Å³
M_r = 545.14	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.2092 (3) Å	µ = 0.93 mm⁻¹
b = 14.7061 (4) Å	T = 293 K
c = 13.7540 (4) Å	0.28 × 0.22 × 0.19 mm
β = 97.5214 (8)°

Data collection top

Rigaku R-AXIS RAPID IP diffractometer	5114 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	4322 reflections with I > 2σ(I)
T_min = 0.780, T_max = 0.843	R_int = 0.028
21341 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	25 restraints
wR(F²) = 0.096	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.47 e Å⁻³
5114 reflections	Δρ_min = −0.26 e Å⁻³
380 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Ni1	0.31748 (2)	0.668273 (15)	0.689311 (16)	0.03143 (9)
O1	0.42705 (12)	0.74401 (9)	0.78914 (10)	0.0399 (3)
O2	0.46912 (13)	0.77268 (10)	0.94948 (10)	0.0483 (3)
O3	0.37891 (13)	0.72843 (9)	0.57068 (10)	0.0446 (3)
O4	0.33775 (17)	0.83556 (12)	0.45711 (12)	0.0616 (5)
O5	0.21564 (11)	0.57245 (9)	0.60709 (9)	0.0391 (3)
O6	0.22619 (12)	0.43404 (11)	0.54208 (12)	0.0536 (4)
O1W	0.5686 (2)	0.8674 (2)	0.67787 (15)	0.0930 (8)
O2W	0.53958 (16)	1.06663 (15)	0.88906 (13)	0.0643 (5)
O3W	0.3437 (3)	0.8148 (3)	0.25454 (17)	0.0980 (8)
N1	0.25466 (14)	0.62854 (10)	0.81904 (11)	0.0341 (3)
N2	0.15754 (17)	0.62107 (13)	0.99403 (13)	0.0500 (4)
N3	0.2905 (2)	0.73064 (15)	1.06019 (13)	0.0525 (5)
N4	0.19233 (13)	0.77229 (10)	0.65903 (10)	0.0327 (3)
N5	0.03798 (15)	0.91375 (11)	0.59648 (12)	0.0410 (4)
N6	0.14458 (19)	0.94291 (14)	0.46855 (15)	0.0560 (5)
N7	0.44529 (13)	0.56953 (10)	0.67977 (10)	0.0307 (3)
N8	0.60635 (14)	0.44427 (11)	0.62184 (12)	0.0389 (4)
N9	0.45018 (16)	0.36067 (12)	0.54171 (13)	0.0418 (4)
N10	0.6367 (2)	0.88322 (17)	0.87878 (16)	0.0609 (5)
C1	0.40689 (16)	0.73693 (12)	0.87734 (13)	0.0352 (4)
C2	0.30163 (16)	0.67882 (12)	0.89515 (13)	0.0331 (4)
C3	0.25094 (18)	0.67630 (13)	0.98471 (14)	0.0389 (4)
C4	0.1158 (2)	0.56992 (16)	0.91715 (16)	0.0528 (5)
H4	0.0521	0.5307	0.9229	0.063*
C5	0.16254 (19)	0.57242 (14)	0.82959 (15)	0.0429 (4)
H5	0.1305	0.5354	0.7778	0.052*
C6	0.31612 (18)	0.79401 (13)	0.53101 (13)	0.0385 (4)
C7	0.21035 (17)	0.82128 (11)	0.58056 (13)	0.0321 (4)
C8	0.13109 (17)	0.89357 (12)	0.54759 (13)	0.0368 (4)
C9	0.02365 (18)	0.86309 (14)	0.67384 (14)	0.0413 (4)
H9	−0.0410	0.8758	0.7077	0.050*
C10	0.09911 (17)	0.79277 (14)	0.70670 (13)	0.0390 (4)
H10	0.0855	0.7596	0.7618	0.047*
C11	0.27182 (16)	0.50055 (13)	0.58777 (13)	0.0345 (4)
C12	0.40521 (15)	0.49993 (12)	0.62341 (12)	0.0294 (3)
C13	0.48649 (16)	0.43358 (12)	0.59462 (12)	0.0316 (4)
C14	0.64164 (17)	0.51541 (14)	0.67792 (15)	0.0418 (4)
H14	0.7237	0.5235	0.6970	0.050*
C15	0.56347 (16)	0.57786 (13)	0.70937 (14)	0.0379 (4)
H15	0.5924	0.6252	0.7507	0.045*
H1W1	0.518 (4)	0.826 (3)	0.681 (3)	0.16 (2)*
H1W2	0.587 (4)	0.871 (3)	0.6200 (14)	0.138 (16)*
H2W1	0.4664 (10)	1.071 (2)	0.8988 (19)	0.079 (10)*
H2W2	0.586 (2)	1.078 (3)	0.9408 (15)	0.123 (15)*
H3W1	0.366 (6)	0.861 (2)	0.290 (3)	0.20 (3)*
H3W2	0.325 (6)	0.772 (3)	0.292 (3)	0.21 (3)*
H31	0.3539 (16)	0.7617 (16)	1.056 (2)	0.064 (8)*
H32	0.259 (2)	0.724 (2)	1.1133 (13)	0.076 (9)*
H61	0.2078 (15)	0.9305 (16)	0.4426 (16)	0.054 (7)*
H62	0.0924 (18)	0.9821 (13)	0.4466 (18)	0.058 (7)*
H91	0.3745 (10)	0.3567 (18)	0.5212 (19)	0.059 (7)*
H92	0.5008 (17)	0.3270 (13)	0.5183 (17)	0.048 (7)*
H101	0.592 (2)	0.8458 (15)	0.9058 (17)	0.079 (10)*
H102	0.627 (3)	0.871 (2)	0.8169 (8)	0.106 (13)*
H103	0.612 (3)	0.9371 (9)	0.887 (2)	0.16 (2)*
H104	0.7095 (10)	0.876 (2)	0.902 (2)	0.124 (15)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.03054 (14)	0.03344 (14)	0.03110 (13)	0.00615 (9)	0.00699 (9)	0.00153 (9)
O1	0.0392 (7)	0.0421 (7)	0.0402 (7)	−0.0052 (6)	0.0123 (6)	−0.0010 (6)
O2	0.0463 (8)	0.0536 (8)	0.0440 (7)	−0.0107 (7)	0.0029 (6)	−0.0063 (7)
O3	0.0452 (8)	0.0472 (7)	0.0454 (7)	0.0188 (6)	0.0214 (6)	0.0114 (6)
O4	0.0649 (11)	0.0760 (11)	0.0496 (9)	0.0243 (9)	0.0285 (8)	0.0262 (8)
O5	0.0292 (6)	0.0472 (7)	0.0400 (7)	0.0099 (6)	0.0012 (5)	−0.0059 (6)
O6	0.0326 (7)	0.0540 (9)	0.0713 (10)	0.0016 (6)	−0.0046 (7)	−0.0237 (8)
O1W	0.0979 (17)	0.131 (2)	0.0520 (11)	−0.0539 (16)	0.0174 (11)	−0.0013 (12)
O2W	0.0414 (9)	0.0925 (13)	0.0577 (10)	−0.0038 (9)	0.0021 (8)	−0.0103 (10)
O3W	0.0917 (18)	0.144 (2)	0.0590 (12)	−0.0021 (17)	0.0121 (12)	−0.0216 (15)
N1	0.0345 (8)	0.0350 (8)	0.0325 (7)	0.0019 (6)	0.0037 (6)	0.0027 (6)
N2	0.0528 (11)	0.0581 (11)	0.0419 (9)	−0.0058 (9)	0.0163 (8)	0.0059 (8)
N3	0.0585 (12)	0.0643 (12)	0.0360 (9)	−0.0039 (10)	0.0113 (9)	−0.0049 (9)
N4	0.0335 (8)	0.0342 (7)	0.0312 (7)	0.0067 (6)	0.0067 (6)	−0.0003 (6)
N5	0.0408 (9)	0.0391 (8)	0.0427 (8)	0.0131 (7)	0.0042 (7)	−0.0013 (7)
N6	0.0556 (12)	0.0564 (11)	0.0582 (11)	0.0224 (10)	0.0161 (10)	0.0245 (10)
N7	0.0276 (7)	0.0340 (7)	0.0303 (7)	0.0042 (6)	0.0032 (6)	0.0011 (6)
N8	0.0298 (8)	0.0432 (8)	0.0443 (8)	0.0071 (7)	0.0074 (7)	0.0015 (7)
N9	0.0349 (9)	0.0419 (9)	0.0498 (9)	0.0042 (7)	0.0107 (8)	−0.0092 (8)
N10	0.0507 (12)	0.0779 (16)	0.0551 (12)	−0.0199 (11)	0.0108 (10)	−0.0007 (11)
C1	0.0343 (9)	0.0340 (9)	0.0374 (9)	0.0032 (7)	0.0053 (7)	−0.0006 (8)
C2	0.0325 (9)	0.0349 (9)	0.0317 (8)	0.0058 (7)	0.0037 (7)	0.0029 (7)
C3	0.0408 (10)	0.0432 (10)	0.0329 (9)	0.0067 (8)	0.0054 (8)	0.0042 (8)
C4	0.0518 (13)	0.0584 (13)	0.0501 (12)	−0.0145 (11)	0.0138 (10)	0.0067 (11)
C5	0.0442 (11)	0.0436 (10)	0.0407 (10)	−0.0084 (9)	0.0046 (8)	0.0021 (8)
C6	0.0408 (10)	0.0426 (10)	0.0335 (9)	0.0070 (8)	0.0104 (8)	0.0023 (8)
C7	0.0338 (9)	0.0319 (8)	0.0306 (8)	0.0043 (7)	0.0039 (7)	−0.0011 (7)
C8	0.0387 (10)	0.0340 (9)	0.0368 (9)	0.0043 (8)	0.0014 (8)	0.0007 (7)
C9	0.0376 (10)	0.0478 (11)	0.0393 (9)	0.0113 (9)	0.0084 (8)	−0.0069 (9)
C10	0.0387 (10)	0.0461 (10)	0.0339 (9)	0.0089 (8)	0.0111 (8)	−0.0001 (8)
C11	0.0280 (8)	0.0433 (10)	0.0321 (8)	0.0044 (7)	0.0036 (7)	−0.0003 (8)
C12	0.0269 (8)	0.0330 (8)	0.0288 (8)	0.0038 (7)	0.0050 (6)	0.0027 (7)
C13	0.0315 (9)	0.0335 (8)	0.0306 (8)	0.0042 (7)	0.0076 (7)	0.0037 (7)
C14	0.0253 (9)	0.0500 (11)	0.0496 (11)	0.0033 (8)	0.0027 (8)	−0.0003 (9)
C15	0.0304 (9)	0.0412 (10)	0.0409 (9)	0.0008 (8)	0.0006 (7)	−0.0029 (8)

Geometric parameters (Å, º) top

Ni1—O1	2.0476 (13)	N6—C8	1.332 (3)
Ni1—O3	2.0526 (13)	N6—H61	0.853 (10)
Ni1—O5	2.0567 (13)	N6—H62	0.849 (10)
Ni1—N7	2.0561 (14)	N7—C12	1.326 (2)
Ni1—N4	2.0805 (14)	N7—C15	1.340 (2)
Ni1—N1	2.0857 (15)	N8—C14	1.329 (3)
O1—C1	1.267 (2)	N8—C13	1.356 (2)
O2—C1	1.252 (2)	N9—C13	1.329 (2)
O3—C6	1.274 (2)	N9—H91	0.860 (10)
O4—C6	1.237 (2)	N9—H92	0.848 (10)
O5—C11	1.276 (2)	N10—H101	0.861 (9)
O6—C11	1.237 (2)	N10—H102	0.861 (9)
O1W—H1W1	0.84 (1)	N10—H103	0.853 (9)
O1W—H1W2	0.85 (1)	N10—H104	0.844 (9)
O2W—H2W1	0.85 (1)	C1—C2	1.503 (3)
O2W—H2W2	0.84 (1)	C2—C3	1.423 (3)
O3W—H3W1	0.85 (1)	C4—C5	1.375 (3)
O3W—H3W2	0.86 (1)	C4—H4	0.9300
N1—C2	1.332 (2)	C5—H5	0.9300
N1—C5	1.345 (3)	C6—C7	1.498 (3)
N2—C4	1.332 (3)	C7—C8	1.421 (2)
N2—C3	1.344 (3)	C9—C10	1.374 (3)
N3—C3	1.339 (3)	C9—H9	0.9300
N3—H31	0.854 (10)	C10—H10	0.9300
N3—H32	0.858 (10)	C11—C12	1.511 (2)
N4—C7	1.335 (2)	C12—C13	1.426 (2)
N4—C10	1.339 (2)	C14—C15	1.377 (3)
N5—C9	1.326 (3)	C14—H14	0.9300
N5—C8	1.347 (3)	C15—H15	0.9300

O1—Ni1—O3	93.69 (6)	H103—N10—H104	111.9 (14)
O1—Ni1—O5	169.25 (5)	O2—C1—O1	125.01 (18)
O3—Ni1—O5	94.48 (6)	O2—C1—C2	118.53 (16)
O1—Ni1—N7	93.74 (6)	O1—C1—C2	116.43 (16)
O3—Ni1—N7	86.83 (5)	N1—C2—C3	120.28 (17)
O5—Ni1—N7	79.76 (5)	N1—C2—C1	115.18 (16)
O1—Ni1—N4	93.66 (6)	C3—C2—C1	124.54 (17)
O3—Ni1—N4	79.14 (5)	N3—C3—N2	118.03 (19)
O5—Ni1—N4	94.73 (6)	N3—C3—C2	121.75 (19)
N7—Ni1—N4	164.51 (6)	N2—C3—C2	120.16 (18)
O1—Ni1—N1	79.56 (6)	N2—C4—C5	123.1 (2)
O3—Ni1—N1	170.67 (6)	N2—C4—H4	118.5
O5—Ni1—N1	93.05 (6)	C5—C4—H4	118.5
N7—Ni1—N1	99.95 (6)	N1—C5—C4	119.79 (19)
N4—Ni1—N1	94.76 (6)	N1—C5—H5	120.1
C1—O1—Ni1	115.52 (12)	C4—C5—H5	120.1
C6—O3—Ni1	116.28 (12)	O4—C6—O3	124.70 (18)
C11—O5—Ni1	115.38 (11)	O4—C6—C7	119.59 (17)
H1W1—O1W—H1W2	111 (2)	O3—C6—C7	115.71 (16)
H2W1—O2W—H2W2	111 (2)	N4—C7—C8	120.49 (17)
H3W1—O3W—H3W2	108 (2)	N4—C7—C6	115.85 (15)
C2—N1—C5	119.07 (16)	C8—C7—C6	123.65 (17)
C2—N1—Ni1	111.95 (12)	N6—C8—N5	117.76 (17)
C5—N1—Ni1	127.91 (13)	N6—C8—C7	122.34 (18)
C4—N2—C3	117.56 (18)	N5—C8—C7	119.90 (17)
C3—N3—H31	117.1 (19)	N5—C9—C10	123.55 (18)
C3—N3—H32	118 (2)	N5—C9—H9	118.2
H31—N3—H32	124 (3)	C10—C9—H9	118.2
C7—N4—C10	119.01 (15)	N4—C10—C9	119.64 (18)
C7—N4—Ni1	112.91 (12)	N4—C10—H10	120.2
C10—N4—Ni1	128.06 (13)	C9—C10—H10	120.2
C9—N5—C8	117.40 (16)	O6—C11—O5	125.35 (17)
C8—N6—H61	114.4 (17)	O6—C11—C12	119.08 (16)
C8—N6—H62	120.9 (18)	O5—C11—C12	115.57 (16)
H61—N6—H62	125 (2)	N7—C12—C13	120.69 (15)
C12—N7—C15	119.61 (15)	N7—C12—C11	115.47 (15)
C12—N7—Ni1	113.37 (11)	C13—C12—C11	123.71 (16)
C15—N7—Ni1	125.84 (12)	N9—C13—N8	117.77 (16)
C14—N8—C13	117.41 (16)	N9—C13—C12	122.88 (16)
C13—N9—H91	116.9 (18)	N8—C13—C12	119.35 (16)
C13—N9—H92	120.5 (17)	N8—C14—C15	123.63 (17)
H91—N9—H92	121 (2)	N8—C14—H14	118.2
H101—N10—H102	107.1 (13)	C15—C14—H14	118.2
H101—N10—H103	108.6 (14)	N7—C15—C14	119.21 (17)
H102—N10—H103	108.8 (13)	N7—C15—H15	120.4
H101—N10—H104	110.0 (13)	C14—C15—H15	120.4
H102—N10—H104	110.3 (14)

O3—Ni1—O1—C1	170.89 (13)	O1—C1—C2—C3	−167.48 (17)
O5—Ni1—O1—C1	−49.7 (3)	C4—N2—C3—N3	177.4 (2)
N7—Ni1—O1—C1	−102.05 (13)	C4—N2—C3—C2	0.1 (3)
N4—Ni1—O1—C1	91.56 (13)	N1—C2—C3—N3	−175.23 (18)
N1—Ni1—O1—C1	−2.61 (13)	C1—C2—C3—N3	3.6 (3)
O1—Ni1—O3—C6	−96.17 (15)	N1—C2—C3—N2	2.0 (3)
O5—Ni1—O3—C6	90.82 (15)	C1—C2—C3—N2	−179.12 (17)
N7—Ni1—O3—C6	170.28 (15)	C3—N2—C4—C5	−1.0 (3)
N4—Ni1—O3—C6	−3.15 (14)	C2—N1—C5—C4	2.1 (3)
O1—Ni1—O5—C11	−53.7 (3)	Ni1—N1—C5—C4	−164.99 (16)
O3—Ni1—O5—C11	85.68 (13)	N2—C4—C5—N1	0.0 (4)
N7—Ni1—O5—C11	−0.27 (13)	Ni1—O3—C6—O4	−177.33 (18)
N4—Ni1—O5—C11	165.13 (13)	Ni1—O3—C6—C7	3.5 (2)
N1—Ni1—O5—C11	−99.84 (13)	C10—N4—C7—C8	−0.6 (3)
O1—Ni1—N1—C2	8.76 (12)	Ni1—N4—C7—C8	178.20 (13)
O5—Ni1—N1—C2	−179.11 (12)	C10—N4—C7—C6	−179.78 (17)
N7—Ni1—N1—C2	100.76 (12)	Ni1—N4—C7—C6	−1.0 (2)
N4—Ni1—N1—C2	−84.10 (13)	O4—C6—C7—N4	179.16 (19)
O1—Ni1—N1—C5	176.63 (17)	O3—C6—C7—N4	−1.6 (3)
O5—Ni1—N1—C5	−11.24 (17)	O4—C6—C7—C8	0.0 (3)
N7—Ni1—N1—C5	−91.37 (17)	O3—C6—C7—C8	179.19 (17)
N4—Ni1—N1—C5	83.77 (17)	C9—N5—C8—N6	178.60 (19)
O1—Ni1—N4—C7	95.17 (13)	C9—N5—C8—C7	−1.0 (3)
O3—Ni1—N4—C7	2.10 (12)	N4—C7—C8—N6	−178.67 (19)
O5—Ni1—N4—C7	−91.56 (13)	C6—C7—C8—N6	0.5 (3)
N7—Ni1—N4—C7	−23.2 (3)	N4—C7—C8—N5	0.9 (3)
N1—Ni1—N4—C7	174.97 (12)	C6—C7—C8—N5	−179.97 (17)
O1—Ni1—N4—C10	−86.20 (16)	C8—N5—C9—C10	0.8 (3)
O3—Ni1—N4—C10	−179.26 (17)	C7—N4—C10—C9	0.4 (3)
O5—Ni1—N4—C10	87.08 (16)	Ni1—N4—C10—C9	−178.17 (14)
N7—Ni1—N4—C10	155.4 (2)	N5—C9—C10—N4	−0.5 (3)
N1—Ni1—N4—C10	−6.39 (17)	Ni1—O5—C11—O6	177.70 (16)
O1—Ni1—N7—C12	175.68 (12)	Ni1—O5—C11—C12	−3.4 (2)
O3—Ni1—N7—C12	−90.82 (12)	C15—N7—C12—C13	0.5 (2)
O5—Ni1—N7—C12	4.31 (12)	Ni1—N7—C12—C13	168.81 (12)
N4—Ni1—N7—C12	−65.9 (3)	C15—N7—C12—C11	−175.57 (16)
N1—Ni1—N7—C12	95.64 (12)	Ni1—N7—C12—C11	−7.23 (18)
O1—Ni1—N7—C15	−16.83 (15)	O6—C11—C12—N7	−173.77 (17)
O3—Ni1—N7—C15	76.67 (15)	O5—C11—C12—N7	7.2 (2)
O5—Ni1—N7—C15	171.80 (16)	O6—C11—C12—C13	10.3 (3)
N4—Ni1—N7—C15	101.6 (2)	O5—C11—C12—C13	−168.66 (16)
N1—Ni1—N7—C15	−96.87 (15)	C14—N8—C13—N9	−177.44 (18)
Ni1—O1—C1—O2	174.82 (15)	C14—N8—C13—C12	2.5 (3)
Ni1—O1—C1—C2	−3.5 (2)	N7—C12—C13—N9	177.08 (17)
C5—N1—C2—C3	−3.1 (3)	C11—C12—C13—N9	−7.2 (3)
Ni1—N1—C2—C3	166.01 (13)	N7—C12—C13—N8	−2.9 (2)
C5—N1—C2—C1	177.96 (16)	C11—C12—C13—N8	172.81 (16)
Ni1—N1—C2—C1	−12.97 (18)	C13—N8—C14—C15	0.1 (3)
O2—C1—C2—N1	−166.99 (16)	C12—N7—C15—C14	2.1 (3)
O1—C1—C2—N1	11.5 (2)	Ni1—N7—C15—C14	−164.65 (14)
O2—C1—C2—C3	14.1 (3)	N8—C14—C15—N7	−2.5 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H31···O2	0.85 (1)	2.08 (2)	2.740 (3)	134 (2)
N6—H61···O4	0.85 (1)	2.01 (2)	2.701 (3)	138 (2)
N6—H62···N5ⁱ	0.85 (1)	2.15 (1)	2.992 (2)	175 (2)
N9—H91···O6	0.86 (1)	2.07 (2)	2.733 (2)	134 (2)
N9—H92···O3ⁱⁱ	0.85 (1)	2.10 (1)	2.924 (2)	164 (2)
N10—H101···O2	0.86 (1)	1.91 (1)	2.756 (3)	169 (3)
N10—H102···O1w	0.86 (1)	1.94 (1)	2.779 (3)	164 (3)
N10—H103···O2w	0.85 (1)	2.07 (1)	2.919 (3)	172 (3)
N10—H104···N8ⁱⁱⁱ	0.84 (1)	2.36 (2)	3.018 (3)	135 (2)
O1w—H1w1···O1	0.84 (1)	2.25 (2)	2.964 (3)	143 (4)
O1w—H1w2···N2^iv	0.85 (1)	2.00 (1)	2.842 (3)	171 (4)
O2w—H2w1···O5^v	0.85 (1)	2.03 (1)	2.869 (2)	168 (3)
O2w—H2w2···O6^vi	0.84 (1)	1.96 (1)	2.766 (2)	159 (3)
O3w—H3w1···O4	0.85 (1)	2.39 (5)	2.812 (3)	111 (4)

Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x+3/2, y+1/2, −z+3/2; (iv) x+1/2, −y+3/2, z−1/2; (v) −x+1/2, y+1/2, −z+3/2; (vi) x+1/2, −y+3/2, z+1/2.

Experimental details

Crystal data
Chemical formula	(NH₄)[Ni(C₅H₄N₃O₂)₃]·3H₂O
M_r	545.14
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	11.2092 (3), 14.7061 (4), 13.7540 (4)
β (°)	97.5214 (8)
V (Å³)	2247.75 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.93
Crystal size (mm)	0.28 × 0.22 × 0.19

Data collection
Diffractometer	Rigaku R-AXIS RAPID IP diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.780, 0.843
No. of measured, independent and observed [I > 2σ(I)] reflections	21341, 5114, 4322
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.096, 1.02
No. of reflections	5114
No. of parameters	380
No. of restraints	25
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.26

Computer programs: RAPID-AUTO (Rigaku, 1998), CrystalClear (Rigaku/MSC, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2009).

Selected bond lengths (Å) top

Ni1—O1	2.0476 (13)	Ni1—N7	2.0561 (14)
Ni1—O3	2.0526 (13)	Ni1—N4	2.0805 (14)
Ni1—O5	2.0567 (13)	Ni1—N1	2.0857 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H31···O2	0.85 (1)	2.08 (2)	2.740 (3)	134 (2)
N6—H61···O4	0.85 (1)	2.01 (2)	2.701 (3)	138 (2)
N6—H62···N5ⁱ	0.85 (1)	2.15 (1)	2.992 (2)	175 (2)
N9—H91···O6	0.86 (1)	2.07 (2)	2.733 (2)	134 (2)
N9—H92···O3ⁱⁱ	0.85 (1)	2.10 (1)	2.924 (2)	164 (2)
N10—H101···O2	0.86 (1)	1.91 (1)	2.756 (3)	169 (3)
N10—H102···O1w	0.86 (1)	1.94 (1)	2.779 (3)	164 (3)
N10—H103···O2w	0.85 (1)	2.07 (1)	2.919 (3)	172 (3)
N10—H104···N8ⁱⁱⁱ	0.84 (1)	2.36 (2)	3.018 (3)	135 (2)
O1w—H1w1···O1	0.84 (1)	2.25 (2)	2.964 (3)	143 (4)
O1w—H1w2···N2^iv	0.85 (1)	2.00 (1)	2.842 (3)	171 (4)
O2w—H2w1···O5^v	0.85 (1)	2.03 (1)	2.869 (2)	168 (3)
O2w—H2w2···O6^vi	0.84 (1)	1.96 (1)	2.766 (2)	159 (3)
O3w—H3w1···O4	0.85 (1)	2.39 (5)	2.812 (3)	111 (4)

Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x+1, −y+1, −z+1; (iii) −x+3/2, y+1/2, −z+3/2; (iv) x+1/2, −y+3/2, z−1/2; (v) −x+1/2, y+1/2, −z+3/2; (vi) x+1/2, −y+3/2, z+1/2.

Acknowledgements

We thank the Key Project of the Natural Science Foundation of Heilongjiang Province (No. ZD200903), the Scientific Fund of Remarkable Teachers of Heilongjiang Province (No. 1054 G036), Heilongjiang University and the University of Malaya for supporting this study.

References

Barbour, L. J. (2001). J. Supramol. Chem. 1, 189–191. CrossRef CAS Google Scholar
Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Ptasiewicz-Bak, H. & Leciejewicz, B. (1999). Pol. J. Chem. 73, 717–725. CAS Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Rigaku/MSC (2002). CrystalClear. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2009). publCIF. In preparation. Google Scholar