Hydroxonium creatininium bis­(pyridine-2,6-dicarboxyl­ato-κ3O2,N,O6)nickel­ate(II) trihydrate

Attar Gharamaleki, J.; Aghabozorg, H.; Derikvand, Z.; Yousefi, M.

doi:10.1107/S1600536809022053

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Pages m824-m825

doi:10.1107/S1600536809022053

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Hydroxonium creatininium bis(pyridine-2,6-dicarboxylato-κ³O²,N,O⁶)nickelate(II) trihydrate

Jafar Attar Gharamaleki,^a Hossein Aghabozorg,^b ^* Zohreh Derikvand ^c and Mohammad Yousefi ^d

^aYoung Researchers Club, Islamic Azad University, North Tehran Branch, Tehran, Iran, ^bFaculty of Chemistry, Islamic Azad University, North Tehran Branch, Tehran, Iran, ^cDepartment of Chemistry, Faculty of Science, Islamic Azad University, Khorramabad Branch, Khorramabad, Iran, and ^dDepartment of Chemistry, Islamic Azad University, Shahr-e Rey Branch, Tehran, Iran
^*Correspondence e-mail: haghabozorg@yahoo.com

(Received 19 May 2009; accepted 10 June 2009; online 27 June 2009)

The title compound, (C₄H₈N₃O)(H₃O)[Ni(C₇H₃NO₄)₂]·3H₂O, exhibits isotypism with its Co^II analogue. All intramolecular distances and angles are similar for the two structures. This applies also for the intermolecular forces, consisting of O—H⋯O and N—H⋯O hydrogen bonds and π–π interactions [with centroid–centroid distances of 3.428 (2) and 3.579 (2) Å], that lead to a cohesion of the structure.

Related literature

For background to proton-transfer agents, see: Aghabozorg, Manteghi et al. (2008 ); Soleimannejad et al. (2005 ); Aghabozorg, Ramezanipour et al. (2008 ). For related structures, see: Moghimi et al. (2004 , 2005 ); Aghabozorg, Motyeian et al. (2008 ); Aghabozorg, Derikvand et al. (2008 ). For the isotypic Co compound, see: Aghabozorg et al. (2009 ).

Experimental

Crystal data

(C₄H₈N₃O)(H₃O)[Ni(C₇H₃NO₄)₂]·3H₂O
M_r = 576.12
Triclinic, $[P \overline 1]$
a = 8.1466 (9) Å
b = 10.7420 (12) Å
c = 13.5061 (15) Å
α = 74.890 (2)°
β = 89.944 (2)°
γ = 87.564 (3)°
V = 1140.0 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.93 mm⁻¹
T = 120 K
0.18 × 0.14 × 0.12 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 1998 ) T_min = 0.803, T_max = 0.896
11509 measured reflections
5404 independent reflections
3827 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.134
S = 1.00
5404 reflections
335 parameters
H-atom parameters constrained
Δρ_max = 0.84 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯O1W	0.85	1.89	2.726 (4)	166
N5—H5NB⋯O3ⁱ	0.93	1.96	2.861 (4)	162
N5—H5NA⋯O8ⁱⁱ	0.83	1.97	2.777 (4)	165
O1W—H1WA⋯O3W	0.85	1.84	2.662 (3)	162
O1W—H1WB⋯O7ⁱⁱ	0.85	1.97	2.804 (3)	166
O2W—H2WA⋯O6	0.85	1.71	2.529 (3)	161
O2W—H2WB⋯O4ⁱⁱⁱ	0.85	1.65	2.480 (3)	165
O2W—H2WC⋯O4W	0.85	1.73	2.521 (3)	155
O3W—H3WA⋯O9	0.85	2.17	2.926 (4)	148
O3W—H3WB⋯O2^iv	0.85	1.94	2.765 (4)	162
O4W—H4WA⋯O2^iv	0.85	1.85	2.682 (4)	165
O4W—H4WB⋯O5^v	0.85	1.91	2.722 (4)	159
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x+1, y+1, z; (iii) x+1, y, z; (iv) x, y+1, z; (v) -x+1, -y+1, -z.

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809022053/pv2161sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809022053/pv2161Isup2.hkl

checkCIF report

Comment top

Two proton transfer compounds have been prepared from creatinine as proton acceptor agent by using pyridine-2,6-dicarboxylic acid (pydcH₂) (Moghimi et al., 2004) and 1,10-phenanthroline-9,13-dicarboxylic acid (phendcH₂) (Soleimannejad et al., 2005) as proton donor agents. Also three complexes of Bi^III (Aghabozorg, Ramezanipour et al., 2008), Zn^II (Moghimi et al., 2005) and Cr^III (Aghabozorg, Derikvand et al., 2008) have been reported by our research group in which the (creatH)⁺ fragment was a part of the the crystal structure; more details can be found in our recently published review article (Aghabozorg, Manteghi et al., 2008). We have now synthesized a novel Ni^II complex, (I), and determined its crystal structure which is presented in this article.

The crystal structure of the title complex, (I), (Fig. 1) contains [Ni(pydc)₂]^2–, creatininium (creatH)⁺ as counter-ion, hydroxonium cation, (H₃O)⁺ and three uncoordinated water molecules. The Ni^II atom is coordinated by two tridentate (pydc)^2– groups and the presence of (creatH)⁺ and (H₃O)⁺ ions balance the negative charge. In the structure of (I), the mean Ni—N and Ni—O bond distances are 1.973 (3) and 2.140 (2) Å, respectively, which are consistent with the corresponding distances reported for similar Ni^II complexes (Aghabozorg, Motyeian et al., 2008). The N-atoms (N1 and N2) of the two (pydc)^2– fragments occupy the axial positions, while O1, O3, O5 and O7 atoms form the equatorial plane. In the anionic complex, the N1—Ni1—N2 angle [174.74 (11)°] deviates slightly from linearity. Therefore, the coordination around the Ni^II atom is distorted octahedral. In addition, the O1—Ni1—O3 and O5—Ni1—O7 angles [155.14 (9) and 155.22 (9)°] indicate that the four carboxylate groups of the two dianions are oriented in a flattened tetrahedral arrangement around the Ni^II atom. The angles O1—Ni1—O5, O1—Ni1—O7, O3—Ni1—O5 and O3—Ni1—O7 are 96.01 (9), 89.16 (9), 89.63 (9) and 95.81 (9)°, respectively. On the other hand, the torsion angles O1—Ni1—O7—C14 and O5—Ni1—O3—C7 are 93.3 (2) and 93.6 (2)°, respectively, indicating that two (pydc)^2– units are almost perpendicular to each other. The angle between two planes passing aromatic rings of (pydc)^2– units is 81.13 (15)°.

A remarkable feature of the title compound is the presence of a large number of O—H···O, N—H···O and C—H···O hydrogen bonds, with D···A distances ranging from 2.480 (3) to 3.415 (4) Å between (creatH)⁺, (H₃O)⁺ and [Ni(pydc)₂]^2– fragments and uncoordinated water molecules. The O2W—O2WB···O4ⁱⁱⁱ hydrogen bond with D···A distance of 2.480 (3) Å, is the strongest (details of the hydrogen bonding geometry have been provided in Table 1). These interactions link the fragments to form a three-dimensional network as shown in Fig. 2. In the structure of (I), the space between two layers of [Ni(pydc)₂]^2– anions is filled with layers of (creatH)⁺, (H₃O)⁺ cations and uncoordinated water molecules (Fig. 2).

There is noticeable π-π stacking interaction between two aromatic rings of (pydc)^2– units, with distances 3.428 (2) Å (1 - x, -y, -z + 1) and 3.579 (2) Å (-x, -y, -z). Also a considerable centrosymmetric C═O···π stacking interactions between C═O groups of carboxylate fragments with aromatic rings of pyridine-2,6-dicarboxylate with distance of 3.488 (1) Å for C═O2···Cg1 (1 - x, -y, -z) [Cg1 is the centroid for N1/C1—C5 ring] are observed in (I) (Fig. 3).

Related literature top

For background to proton-transfer agents, see: Aghabozorg, Manteghi et al. (2008); Soleimannejad et al. (2005); Aghabozorg, Ramezanipour et al. (2008). For related structures, see: (Moghimi et al. (2004, 2005); Aghabozorg, Motyeian et al. (2008); Aghabozorg, Derikvand et al. (2008). For the isotypic Co compound, see: Aghabozorg et al. (2009).

Experimental top

The reaction of nickel(II) chloride hexahydrate (59 mg, 0.25 mmol), creatinine, creat, (57 mg, 0.5 mmol) and pyridine-2,6-dicarboxylic acid, pydcH₂, (83 mg, 0.5 mmol) in a 1:2:2 molar ratio in aqueous solution resulted in the formation of green, (H₃O)(creatH)[Ni(pydc)₂]. 3H₂O crystals.

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT-Plus (Bruker, 1998); data reduction: SAINT-Plus (Bruker, 1998); 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, thermal ellipsoids are shown at 50% probability level.
	Fig. 2. Unit cell packing diagram of the title compound, hydrogen bonds are shown as dashed lines and H-atoms not involved in H-bonds have been excluded.
	Fig. 3. π-π Stacking interaction between two aromatic rings of (pydc)^2– units.

Hydroxonium creatininium bis(pyridine-2,6-dicarboxylato)nickelate(II) trihydrate top

Crystal data top

(C₄H₈N₃O)(H₃O)[Ni(C₇H₃NO₄)₂]·3H₂O	Z = 2
M_r = 576.12	F(000) = 596
Triclinic, P1	D_x = 1.678 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1466 (9) Å	Cell parameters from 1838 reflections
b = 10.7420 (12) Å	θ = 2.8–24.2°
c = 13.5061 (15) Å	µ = 0.93 mm⁻¹
α = 74.890 (2)°	T = 120 K
β = 89.944 (2)°	Prism, green
γ = 87.564 (3)°	0.18 × 0.14 × 0.12 mm
V = 1140.0 (2) Å³

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	5404 independent reflections
Radiation source: fine-focus sealed tube	3827 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
ω scans	θ_max = 28.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −10→10
T_min = 0.803, T_max = 0.896	k = −14→14
11509 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)] = 0.053	Hydrogen site location: mixed
wR(F²) = 0.134	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0405P)² + 2.37P] where P = (F_o² + 2F_c²)/3
5404 reflections	(Δ/σ)_max = 0.001
335 parameters	Δρ_max = 0.84 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

(C₄H₈N₃O)(H₃O)[Ni(C₇H₃NO₄)₂]·3H₂O	γ = 87.564 (3)°
M_r = 576.12	V = 1140.0 (2) Å³
Triclinic, P1	Z = 2
a = 8.1466 (9) Å	Mo Kα radiation
b = 10.7420 (12) Å	µ = 0.93 mm⁻¹
c = 13.5061 (15) Å	T = 120 K
α = 74.890 (2)°	0.18 × 0.14 × 0.12 mm
β = 89.944 (2)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	5404 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	3827 reflections with I > 2σ(I)
T_min = 0.803, T_max = 0.896	R_int = 0.046
11509 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.134	H-atom parameters constrained
S = 1.00	Δρ_max = 0.84 e Å⁻³
5404 reflections	Δρ_min = −0.37 e Å⁻³
335 parameters

Special details top

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 (Å²) top

	x	y	z	U_iso*/U_eq
Ni1	0.26883 (5)	0.07342 (4)	0.22939 (3)	0.01905 (13)
O1	0.4241 (3)	−0.0881 (2)	0.23014 (17)	0.0225 (5)
O2	0.4819 (3)	−0.2302 (2)	0.13848 (18)	0.0245 (5)
O3	0.0829 (3)	0.2229 (2)	0.16633 (17)	0.0211 (5)
O4	−0.0572 (3)	0.3100 (2)	0.01983 (17)	0.0254 (5)
O5	0.4573 (3)	0.2152 (2)	0.18788 (17)	0.0220 (5)
O6	0.6101 (3)	0.3404 (2)	0.25748 (18)	0.0271 (5)
O7	0.1100 (3)	−0.0493 (2)	0.33115 (17)	0.0228 (5)
O8	0.0881 (3)	−0.1386 (2)	0.50037 (18)	0.0271 (5)
N1	0.2282 (3)	0.0494 (2)	0.0918 (2)	0.0165 (5)
N2	0.3261 (3)	0.1077 (2)	0.3616 (2)	0.0161 (5)
C1	0.3098 (4)	−0.0458 (3)	0.0640 (2)	0.0175 (6)
C2	0.2950 (4)	−0.0601 (3)	−0.0352 (2)	0.0201 (7)
H2A	0.3515	−0.1291	−0.0547	0.024*
C3	0.1952 (4)	0.0295 (3)	−0.1048 (3)	0.0221 (7)
H3A	0.1842	0.0227	−0.1732	0.027*
C4	0.1118 (4)	0.1285 (3)	−0.0749 (2)	0.0208 (7)
H4A	0.0440	0.1904	−0.1221	0.025*
C5	0.1297 (4)	0.1347 (3)	0.0252 (2)	0.0174 (6)
C6	0.4140 (4)	−0.1286 (3)	0.1508 (2)	0.0189 (7)
C7	0.0456 (4)	0.2315 (3)	0.0738 (2)	0.0203 (7)
C8	0.4375 (4)	0.1947 (3)	0.3651 (2)	0.0175 (6)
C9	0.4809 (4)	0.2192 (3)	0.4569 (2)	0.0207 (7)
H9A	0.5607	0.2803	0.4591	0.025*
C10	0.4039 (4)	0.1512 (3)	0.5470 (2)	0.0212 (7)
H10A	0.4291	0.1671	0.6112	0.025*
C11	0.2910 (4)	0.0610 (3)	0.5404 (2)	0.0220 (7)
H11A	0.2383	0.0134	0.6003	0.026*
C12	0.2554 (4)	0.0409 (3)	0.4455 (2)	0.0168 (6)
C13	0.5092 (4)	0.2559 (3)	0.2620 (2)	0.0202 (7)
C14	0.1407 (4)	−0.0569 (3)	0.4255 (2)	0.0193 (7)
O9	0.7005 (3)	0.4732 (2)	0.46109 (18)	0.0300 (6)
N3	0.8635 (3)	0.5880 (3)	0.5417 (2)	0.0186 (6)
H3N	0.9098	0.6328	0.4886	0.028*
N4	0.7837 (3)	0.5199 (3)	0.7029 (2)	0.0202 (6)
N5	0.9931 (3)	0.6668 (3)	0.6669 (2)	0.0213 (6)
H5NB	0.9862	0.6905	0.7286	0.032*
H5NA	1.0388	0.7217	0.6217	0.032*
C15	0.7458 (4)	0.5019 (3)	0.5378 (3)	0.0217 (7)
C16	0.8858 (4)	0.5953 (3)	0.6403 (2)	0.0185 (6)
C17	0.6828 (4)	0.4533 (3)	0.6458 (3)	0.0226 (7)
H17A	0.5647	0.4771	0.6499	0.027*
H17B	0.6996	0.3585	0.6710	0.027*
C18	0.7939 (5)	0.4855 (4)	0.8144 (3)	0.0288 (8)
H18A	0.8137	0.5627	0.8376	0.043*
H18B	0.8844	0.4214	0.8376	0.043*
H18C	0.6904	0.4491	0.8429	0.043*
O1W	0.9969 (3)	0.7014 (2)	0.35667 (18)	0.0257 (5)
H1WA	0.9086	0.6978	0.3243	0.038*
H1WB	1.0206	0.7804	0.3398	0.038*
O2W	0.7807 (3)	0.4512 (2)	0.10606 (19)	0.0310 (6)
H2WA	0.7267	0.3996	0.1517	0.046*
H2WB	0.8208	0.4006	0.0723	0.046*
H2WC	0.7360	0.5102	0.0580	0.046*
O3W	0.7459 (3)	0.6405 (3)	0.2550 (2)	0.0385 (7)
H3WA	0.7188	0.5734	0.3000	0.058*
H3WB	0.6564	0.6811	0.2316	0.058*
O4W	0.6023 (4)	0.6403 (3)	0.0074 (2)	0.0454 (8)
H4WA	0.5592	0.6919	0.0393	0.068*
H4WB	0.5964	0.6694	−0.0574	0.068*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0227 (2)	0.0187 (2)	0.0156 (2)	−0.00178 (16)	−0.00045 (16)	−0.00419 (16)
O1	0.0295 (13)	0.0209 (12)	0.0176 (11)	0.0012 (10)	0.0011 (10)	−0.0064 (9)
O2	0.0315 (13)	0.0208 (12)	0.0220 (12)	0.0086 (10)	−0.0026 (10)	−0.0087 (10)
O3	0.0254 (12)	0.0215 (12)	0.0168 (11)	0.0008 (10)	0.0001 (9)	−0.0062 (9)
O4	0.0287 (13)	0.0262 (13)	0.0193 (12)	0.0074 (10)	−0.0034 (10)	−0.0040 (10)
O5	0.0249 (12)	0.0263 (12)	0.0155 (11)	−0.0045 (10)	0.0021 (9)	−0.0060 (9)
O6	0.0306 (14)	0.0279 (13)	0.0220 (12)	−0.0110 (11)	0.0015 (10)	−0.0038 (10)
O7	0.0294 (13)	0.0204 (12)	0.0186 (12)	−0.0068 (10)	0.0023 (10)	−0.0042 (9)
O8	0.0349 (14)	0.0231 (12)	0.0222 (12)	−0.0078 (11)	0.0060 (10)	−0.0027 (10)
N1	0.0151 (13)	0.0140 (12)	0.0186 (13)	−0.0019 (10)	0.0003 (10)	−0.0009 (10)
N2	0.0170 (13)	0.0132 (12)	0.0167 (13)	0.0031 (10)	0.0000 (10)	−0.0023 (10)
C1	0.0153 (15)	0.0184 (15)	0.0193 (16)	−0.0025 (12)	0.0014 (12)	−0.0058 (12)
C2	0.0194 (16)	0.0195 (16)	0.0226 (17)	−0.0040 (13)	0.0014 (13)	−0.0071 (13)
C3	0.0268 (18)	0.0234 (17)	0.0170 (16)	−0.0025 (14)	−0.0039 (13)	−0.0065 (13)
C4	0.0216 (17)	0.0204 (16)	0.0178 (16)	−0.0010 (13)	−0.0030 (13)	−0.0002 (12)
C5	0.0180 (16)	0.0158 (15)	0.0178 (15)	−0.0031 (12)	0.0026 (12)	−0.0031 (12)
C6	0.0182 (16)	0.0195 (16)	0.0187 (16)	−0.0032 (13)	0.0012 (12)	−0.0039 (13)
C7	0.0229 (17)	0.0175 (15)	0.0188 (16)	0.0005 (13)	−0.0011 (13)	−0.0019 (12)
C8	0.0146 (15)	0.0129 (14)	0.0233 (16)	0.0017 (12)	0.0007 (12)	−0.0021 (12)
C9	0.0204 (16)	0.0193 (16)	0.0216 (16)	0.0027 (13)	−0.0028 (13)	−0.0046 (13)
C10	0.0263 (18)	0.0221 (16)	0.0157 (15)	0.0054 (14)	−0.0040 (13)	−0.0066 (13)
C11	0.0242 (17)	0.0226 (17)	0.0164 (16)	0.0071 (14)	0.0006 (13)	−0.0012 (13)
C12	0.0148 (15)	0.0151 (15)	0.0193 (16)	0.0040 (12)	0.0008 (12)	−0.0032 (12)
C13	0.0204 (16)	0.0196 (16)	0.0195 (16)	0.0003 (13)	0.0004 (13)	−0.0030 (13)
C14	0.0180 (16)	0.0168 (15)	0.0232 (17)	0.0015 (12)	0.0016 (13)	−0.0055 (13)
O9	0.0341 (14)	0.0351 (14)	0.0227 (13)	−0.0115 (12)	−0.0032 (11)	−0.0094 (11)
N3	0.0211 (14)	0.0209 (14)	0.0132 (13)	−0.0024 (11)	0.0022 (10)	−0.0035 (10)
N4	0.0246 (15)	0.0185 (13)	0.0165 (13)	−0.0040 (11)	0.0016 (11)	−0.0021 (11)
N5	0.0267 (15)	0.0225 (14)	0.0140 (13)	−0.0018 (12)	−0.0001 (11)	−0.0034 (11)
C15	0.0211 (16)	0.0188 (16)	0.0241 (17)	−0.0007 (13)	−0.0012 (13)	−0.0037 (13)
C16	0.0199 (16)	0.0165 (15)	0.0179 (16)	0.0050 (12)	0.0009 (12)	−0.0032 (12)
C17	0.0220 (17)	0.0231 (17)	0.0220 (17)	−0.0050 (14)	−0.0002 (13)	−0.0043 (13)
C18	0.040 (2)	0.0268 (18)	0.0181 (17)	−0.0089 (16)	0.0017 (15)	−0.0015 (14)
O1W	0.0261 (13)	0.0248 (13)	0.0248 (13)	−0.0066 (10)	−0.0014 (10)	−0.0034 (10)
O2W	0.0373 (15)	0.0255 (13)	0.0266 (13)	0.0023 (11)	0.0072 (11)	−0.0013 (11)
O3W	0.0363 (16)	0.0365 (15)	0.0345 (15)	−0.0107 (12)	−0.0101 (12)	0.0067 (12)
O4W	0.082 (2)	0.0346 (15)	0.0169 (13)	0.0270 (15)	−0.0012 (13)	−0.0065 (11)

Geometric parameters (Å, º) top

Ni1—N1	1.972 (3)	C10—C11	1.384 (5)
Ni1—N2	1.974 (3)	C10—H10A	0.9500
Ni1—O1	2.101 (2)	C11—C12	1.387 (4)
Ni1—O7	2.121 (2)	C11—H11A	0.9500
Ni1—O3	2.163 (2)	C12—C14	1.511 (4)
Ni1—O5	2.178 (2)	O9—C15	1.218 (4)
O1—C6	1.262 (4)	N3—C16	1.368 (4)
O2—C6	1.252 (4)	N3—C15	1.370 (4)
O3—C7	1.265 (4)	N3—H3N	0.8511
O4—C7	1.251 (4)	N4—C16	1.327 (4)
O5—C13	1.272 (4)	N4—C18	1.455 (4)
O6—C13	1.240 (4)	N4—C17	1.457 (4)
O7—C14	1.280 (4)	N5—C16	1.298 (4)
O8—C14	1.243 (4)	N5—H5NB	0.9334
N1—C1	1.330 (4)	N5—H5NA	0.8300
N1—C5	1.342 (4)	C15—C17	1.512 (5)
N2—C12	1.320 (4)	C17—H17A	0.9900
N2—C8	1.340 (4)	C17—H17B	0.9900
C1—C2	1.394 (4)	C18—H18A	0.9800
C1—C6	1.509 (4)	C18—H18B	0.9800
C2—C3	1.391 (5)	C18—H18C	0.9800
C2—H2A	0.9500	O1W—H1WA	0.8500
C3—C4	1.385 (5)	O1W—H1WB	0.8500
C3—H3A	0.9500	O2W—H2WA	0.8499
C4—C5	1.379 (4)	O2W—H2WB	0.8500
C4—H4A	0.9500	O2W—H2WC	0.8500
C5—C7	1.509 (4)	O3W—H3WA	0.8500
C8—C9	1.382 (5)	O3W—H3WB	0.8500
C8—C13	1.505 (4)	O4W—H4WA	0.8500
C9—C10	1.408 (5)	O4W—H4WB	0.8500
C9—H9A	0.9500

N1—Ni1—N2	174.74 (11)	C8—C9—H9A	120.8
N1—Ni1—O1	78.05 (10)	C10—C9—H9A	120.8
N2—Ni1—O1	101.80 (10)	C11—C10—C9	118.8 (3)
N1—Ni1—O7	106.74 (10)	C11—C10—H10A	120.6
N2—Ni1—O7	78.49 (10)	C9—C10—H10A	120.6
O1—Ni1—O7	89.16 (9)	C10—C11—C12	119.3 (3)
N1—Ni1—O3	77.19 (9)	C10—C11—H11A	120.3
N2—Ni1—O3	103.06 (9)	C12—C11—H11A	120.3
O1—Ni1—O3	155.14 (9)	N2—C12—C11	121.0 (3)
O7—Ni1—O3	95.81 (9)	N2—C12—C14	112.9 (3)
N1—Ni1—O5	98.03 (9)	C11—C12—C14	126.1 (3)
N2—Ni1—O5	76.74 (10)	O6—C13—O5	126.9 (3)
O1—Ni1—O5	96.01 (9)	O6—C13—C8	117.6 (3)
O7—Ni1—O5	155.22 (9)	O5—C13—C8	115.5 (3)
O3—Ni1—O5	89.63 (9)	O8—C14—O7	125.9 (3)
C6—O1—Ni1	114.6 (2)	O8—C14—C12	118.2 (3)
C7—O3—Ni1	113.8 (2)	O7—C14—C12	115.9 (3)
C13—O5—Ni1	114.4 (2)	C16—N3—C15	110.3 (3)
C14—O7—Ni1	112.9 (2)	C16—N3—H3N	126.5
C1—N1—C5	121.1 (3)	C15—N3—H3N	123.1
C1—N1—Ni1	118.9 (2)	C16—N4—C18	125.2 (3)
C5—N1—Ni1	119.8 (2)	C16—N4—C17	110.3 (3)
C12—N2—C8	121.4 (3)	C18—N4—C17	123.3 (3)
C12—N2—Ni1	118.5 (2)	C16—N5—H5NB	122.1
C8—N2—Ni1	120.1 (2)	C16—N5—H5NA	119.2
N1—C1—C2	120.9 (3)	H5NB—N5—H5NA	111.9
N1—C1—C6	111.8 (3)	O9—C15—N3	125.8 (3)
C2—C1—C6	127.3 (3)	O9—C15—C17	127.5 (3)
C3—C2—C1	118.1 (3)	N3—C15—C17	106.7 (3)
C3—C2—H2A	120.9	N5—C16—N4	125.9 (3)
C1—C2—H2A	120.9	N5—C16—N3	123.6 (3)
C4—C3—C2	120.3 (3)	N4—C16—N3	110.6 (3)
C4—C3—H3A	119.8	N4—C17—C15	102.1 (3)
C2—C3—H3A	119.8	N4—C17—H17A	111.3
C5—C4—C3	118.3 (3)	C15—C17—H17A	111.3
C5—C4—H4A	120.9	N4—C17—H17B	111.3
C3—C4—H4A	120.9	C15—C17—H17B	111.3
N1—C5—C4	121.3 (3)	H17A—C17—H17B	109.2
N1—C5—C7	112.1 (3)	N4—C18—H18A	109.5
C4—C5—C7	126.6 (3)	N4—C18—H18B	109.5
O2—C6—O1	125.8 (3)	H18A—C18—H18B	109.5
O2—C6—C1	118.1 (3)	N4—C18—H18C	109.5
O1—C6—C1	116.1 (3)	H18A—C18—H18C	109.5
O4—C7—O3	126.4 (3)	H18B—C18—H18C	109.5
O4—C7—C5	117.0 (3)	H1WA—O1W—H1WB	105.5
O3—C7—C5	116.6 (3)	H2WA—O2W—H2WB	101.4
N2—C8—C9	121.1 (3)	H2WA—O2W—H2WC	123.5
N2—C8—C13	113.2 (3)	H2WB—O2W—H2WC	100.7
C9—C8—C13	125.7 (3)	H3WA—O3W—H3WB	106.0
C8—C9—C10	118.4 (3)	H4WA—O4W—H4WB	113.1

N1—Ni1—O1—C6	−3.8 (2)	Ni1—O1—C6—O2	−172.4 (3)
N2—Ni1—O1—C6	−178.4 (2)	Ni1—O1—C6—C1	7.4 (3)
O7—Ni1—O1—C6	103.5 (2)	N1—C1—C6—O2	171.8 (3)
O3—Ni1—O1—C6	1.4 (4)	C2—C1—C6—O2	−8.7 (5)
O5—Ni1—O1—C6	−100.8 (2)	N1—C1—C6—O1	−8.1 (4)
N1—Ni1—O3—C7	−4.7 (2)	C2—C1—C6—O1	171.5 (3)
N2—Ni1—O3—C7	169.9 (2)	Ni1—O3—C7—O4	−179.7 (3)
O1—Ni1—O3—C7	−10.0 (4)	Ni1—O3—C7—C5	2.4 (3)
O7—Ni1—O3—C7	−110.6 (2)	N1—C5—C7—O4	−175.4 (3)
O5—Ni1—O3—C7	93.6 (2)	C4—C5—C7—O4	4.0 (5)
N1—Ni1—O5—C13	178.0 (2)	N1—C5—C7—O3	2.7 (4)
N2—Ni1—O5—C13	−2.5 (2)	C4—C5—C7—O3	−177.9 (3)
O1—Ni1—O5—C13	−103.3 (2)	C12—N2—C8—C9	−1.0 (4)
O7—Ni1—O5—C13	−2.2 (4)	Ni1—N2—C8—C9	−179.2 (2)
O3—Ni1—O5—C13	101.0 (2)	C12—N2—C8—C13	177.3 (3)
N1—Ni1—O7—C14	170.5 (2)	Ni1—N2—C8—C13	−1.0 (3)
N2—Ni1—O7—C14	−8.9 (2)	N2—C8—C9—C10	−0.6 (5)
O1—Ni1—O7—C14	93.3 (2)	C13—C8—C9—C10	−178.7 (3)
O3—Ni1—O7—C14	−111.1 (2)	C8—C9—C10—C11	1.4 (5)
O5—Ni1—O7—C14	−9.3 (4)	C9—C10—C11—C12	−0.7 (5)
O1—Ni1—N1—C1	−1.0 (2)	C8—N2—C12—C11	1.8 (4)
O7—Ni1—N1—C1	−86.4 (2)	Ni1—N2—C12—C11	−179.9 (2)
O3—Ni1—N1—C1	−178.7 (2)	C8—N2—C12—C14	−176.9 (3)
O5—Ni1—N1—C1	93.5 (2)	Ni1—N2—C12—C14	1.4 (3)
O1—Ni1—N1—C5	−175.6 (2)	C10—C11—C12—N2	−0.9 (5)
O7—Ni1—N1—C5	98.9 (2)	C10—C11—C12—C14	177.5 (3)
O3—Ni1—N1—C5	6.6 (2)	Ni1—O5—C13—O6	−176.5 (3)
O5—Ni1—N1—C5	−81.1 (2)	Ni1—O5—C13—C8	2.8 (3)
O1—Ni1—N2—C12	−83.0 (2)	N2—C8—C13—O6	178.0 (3)
O7—Ni1—N2—C12	3.6 (2)	C9—C8—C13—O6	−3.9 (5)
O3—Ni1—N2—C12	97.0 (2)	N2—C8—C13—O5	−1.3 (4)
O5—Ni1—N2—C12	−176.5 (2)	C9—C8—C13—O5	176.8 (3)
O1—Ni1—N2—C8	95.3 (2)	Ni1—O7—C14—O8	−165.9 (3)
O7—Ni1—N2—C8	−178.0 (2)	Ni1—O7—C14—C12	12.2 (3)
O3—Ni1—N2—C8	−84.7 (2)	N2—C12—C14—O8	168.8 (3)
O5—Ni1—N2—C8	1.8 (2)	C11—C12—C14—O8	−9.8 (5)
C5—N1—C1—C2	−0.3 (4)	N2—C12—C14—O7	−9.5 (4)
Ni1—N1—C1—C2	−174.8 (2)	C11—C12—C14—O7	171.9 (3)
C5—N1—C1—C6	179.3 (3)	C16—N3—C15—O9	−178.9 (3)
Ni1—N1—C1—C6	4.8 (3)	C16—N3—C15—C17	2.2 (4)
N1—C1—C2—C3	1.3 (5)	C18—N4—C16—N5	−11.9 (5)
C6—C1—C2—C3	−178.2 (3)	C17—N4—C16—N5	−179.3 (3)
C1—C2—C3—C4	−0.9 (5)	C18—N4—C16—N3	167.9 (3)
C2—C3—C4—C5	−0.5 (5)	C17—N4—C16—N3	0.5 (4)
C1—N1—C5—C4	−1.2 (5)	C15—N3—C16—N5	178.1 (3)
Ni1—N1—C5—C4	173.3 (2)	C15—N3—C16—N4	−1.8 (4)
C1—N1—C5—C7	178.2 (3)	C16—N4—C17—C15	0.8 (3)
Ni1—N1—C5—C7	−7.3 (3)	C18—N4—C17—C15	−166.9 (3)
C3—C4—C5—N1	1.6 (5)	O9—C15—C17—N4	179.4 (3)
C3—C4—C5—C7	−177.8 (3)	N3—C15—C17—N4	−1.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O1W	0.85	1.89	2.726 (4)	166
N5—H5NB···O3ⁱ	0.93	1.96	2.861 (4)	162
N5—H5NA···O8ⁱⁱ	0.83	1.97	2.777 (4)	165
O1W—H1WA···O3W	0.85	1.84	2.662 (3)	162
O1W—H1WB···O7ⁱⁱ	0.85	1.97	2.804 (3)	166
O2W—H2WA···O6	0.85	1.71	2.529 (3)	161
O2W—H2WB···O4ⁱⁱⁱ	0.85	1.65	2.480 (3)	165
O2W—H2WC···O4W	0.85	1.73	2.521 (3)	155
O3W—H3WA···O9	0.85	2.17	2.926 (4)	148
O3W—H3WB···O2^iv	0.85	1.94	2.765 (4)	162
O4W—H4WA···O2^iv	0.85	1.85	2.682 (4)	165
O4W—H4WB···O5^v	0.85	1.91	2.722 (4)	159

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

Experimental details

Crystal data
Chemical formula	(C₄H₈N₃O)(H₃O)[Ni(C₇H₃NO₄)₂]·3H₂O
M_r	576.12
Crystal system, space group	Triclinic, P1
Temperature (K)	120
a, b, c (Å)	8.1466 (9), 10.7420 (12), 13.5061 (15)
α, β, γ (°)	74.890 (2), 89.944 (2), 87.564 (3)
V (Å³)	1140.0 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.93
Crystal size (mm)	0.18 × 0.14 × 0.12

Data collection
Diffractometer	Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.803, 0.896
No. of measured, independent and observed [I > 2σ(I)] reflections	11509, 5404, 3827
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.134, 1.00
No. of reflections	5404
No. of parameters	335
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.84, −0.37

Computer programs: SMART (Bruker, 1998), SAINT-Plus (Bruker, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O1W	0.85	1.891	2.726 (4)	166
N5—H5NB···O3ⁱ	0.93	1.959	2.861 (4)	162
N5—H5NA···O8ⁱⁱ	0.83	1.967	2.777 (4)	165
O1W—H1WA···O3W	0.85	1.840	2.662 (3)	162
O1W—H1WB···O7ⁱⁱ	0.85	1.972	2.804 (3)	166
O2W—H2WA···O6	0.85	1.709	2.529 (3)	161
O2W—H2WB···O4ⁱⁱⁱ	0.85	1.648	2.480 (3)	165
O2W—H2WC···O4W	0.85	1.726	2.521 (3)	155
O3W—H3WA···O9	0.85	2.169	2.926 (4)	148
O3W—H3WB···O2^iv	0.85	1.943	2.765 (4)	162
O4W—H4WA···O2^iv	0.85	1.852	2.682 (4)	165
O4W—H4WB···O5^v	0.85	1.911	2.722 (4)	159

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

References

Aghabozorg, H., Derikvand, Z., Attar Gharamaleki, J. & Yousefi, M. (2009). Acta Cryst. E65, m826–m827. Web of Science CSD CrossRef IUCr Journals Google Scholar
Aghabozorg, H., Derikvand, Z., Olmstead, M. M. & Attar Gharamaleki, J. (2008). Acta Cryst. E64, m1234–m1235. Web of Science CSD CrossRef IUCr Journals Google Scholar
Aghabozorg, H., Manteghi, F. & Sheshmani, S. (2008). J. Iran. Chem. Soc. 5, 184–227. CrossRef CAS Google Scholar
Aghabozorg, H., Motyeian, E., Attar Gharamaleki, J., Soleimannejad, J., Ghadermazi, M. & Spey Sharon, E. (2008). Acta Cryst. E64, m144–m145. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Bruker (1998). SMART, SAINT-Plus and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
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Moghimi, A., Sharif, M. A., Shokrollahi, A., Shamsipur, M. & Aghabozorg, H. (2005). Z. Anorg. Allg. Chem. 631, 902-908. Web of Science CSD CrossRef CAS Google Scholar
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Volume 65| Part 7| July 2009| Pages m824-m825

doi:10.1107/S1600536809022053

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