Benzene-1,3-diammonium bis­(pyridine-2,6-dicarboxyl­ato)nickelate(II) penta­hydrate

Pasdar, H.; Sadat Kashani, S.; Aghabozorg, H.; Notash, B.

doi:10.1107/S1600536810054371

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Pages m193-m194

doi:10.1107/S1600536810054371

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Benzene-1,3-diammonium bis(pyridine-2,6-dicarboxylato)nickelate(II) pentahydrate

Hoda Pasdar,^a Saghi Sadat Kashani,^a ^* Hossein Aghabozorg ^a and Behrouz Notash ^b

^aDepartment of Chemistry, Islamic Azad University, North Tehran Branch, Tehran, Iran, and ^bDepartment of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran 1983963113, Iran
^*Correspondence e-mail: s.sadatkashani@gmail.com

(Received 5 December 2010; accepted 26 December 2010; online 15 January 2011)

In the title compound, (C₆H₁₀N₂)[Ni(C₇H₃NO₄)₂]·5H₂O, the Ni^II ion is six-coordinated by two N and four O atoms from two pyridine-2,6-dicarboxylate ligands in a distorted octahedral fashion. The crystal packing is stabilized by intermolecular O—H⋯O and N—H⋯O and weak C—H⋯O hydrogen bonds and π–π interactions [centroid–centroid distances = 3.4669 (19) and 3.764 (2) Å].

Related literature

For background to proton-transfer compounds, see: Aghabozorg et al. (2008 ). For related structures, see: Aghabozorg et al. (2009 ); Beatty et al. (2002 ); Dobrzycki & Woźniak (2008 ); Attar Gharamaleki et al. (2009 ); Imaz et al. (2007 ); MacDonald et al. (2000 , 2004 ); Sharif et al. (2007 ).

Experimental

Crystal data

(C₆H₁₀N₂)[Ni(C₇H₃NO₄)₂]·5H₂O
M_r = 589.14
Monoclinic, P 2₁ /n
a = 7.5331 (15) Å
b = 18.085 (4) Å
c = 18.578 (4) Å
β = 100.90 (3)°
V = 2485.3 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.86 mm⁻¹
T = 298 K
0.20 × 0.15 × 0.10 mm

Data collection

Stoe IPDS II diffractometer
Absorption correction: numerical (X-RED and X-SHAPE; Stoe & Cie, 2005 ) T_min = 0.855, T_max = 0.920
18439 measured reflections
6687 independent reflections
3608 reflections with I > 2σ(I)
R_int = 0.090

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.086
S = 0.92
6687 reflections
407 parameters
4 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18⋯O2ⁱ	0.93	2.48	3.118 (4)	126
C3—H3⋯O7ⁱⁱ	0.93	2.56	3.284 (4)	135
O13—H13B⋯O9ⁱⁱⁱ	0.82 (5)	2.14 (5)	2.945 (6)	166 (5)
O13—H13A⋯O6^iv	0.76 (4)	2.05 (4)	2.776 (5)	158 (6)
O12—H12B⋯O13^v	0.79 (4)	2.02 (4)	2.808 (5)	176 (8)
O12—H12A⋯O3^vi	0.89 (6)	1.95 (6)	2.838 (4)	174 (5)
O11—H11B⋯O9	0.75 (3)	2.08 (3)	2.829 (4)	173 (5)
O11—H11A⋯O7	0.79 (4)	2.03 (4)	2.798 (4)	163 (4)
O10—H10B⋯O2	0.97 (5)	1.80 (5)	2.750 (4)	168 (5)
O10—H10A⋯O12^vii	0.79 (3)	2.20 (5)	2.880 (5)	146 (6)
O9—H9B⋯O4ⁱⁱ	0.85 (5)	2.07 (5)	2.918 (4)	172 (5)
O9—H9A⋯O10	0.86 (5)	1.91 (5)	2.772 (5)	176 (4)
N4—H4C⋯O6^viii	0.97 (4)	1.78 (4)	2.730 (4)	167 (3)
N4—H4B⋯O4^vi	0.82 (3)	2.05 (4)	2.854 (4)	168 (3)
N4—H4A⋯O11	0.91 (4)	1.94 (4)	2.842 (4)	173 (3)
N3—H3C⋯O1	0.91 (5)	1.82 (5)	2.702 (4)	164 (4)
N3—H3B⋯O8^vii	0.93 (5)	1.85 (5)	2.773 (4)	173 (4)
N3—H3A⋯O12^vii	0.91 (4)	2.07 (4)	2.899 (5)	152 (4)
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+1, -y+2, -z+2; (iii) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iv) -x+2, -y+2, -z+1; (v) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (vi) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (vii) x+1, y, z; (viii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA; data reduction: X-AREA; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810054371/bt5430sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810054371/bt5430Isup2.hkl

checkCIF report

Comment top

Pyridine-2,6-dicarboxylic acid (pydcH₂) was commonly used as an acid in proton transfer systems (Aghabozorg et al. 2008). It has been reported that several proton transfer systems containing the anionic [Ni(pydc)₂]^2- moiety and different cationic parts (Aghabozorg et al. 2009; Attar Gharamaleki et al. 2009; MacDonald et al. 2000; MacDonald et al. 2004; Sharif et al. 2007). In addition, the formation of mono (Beatty et al. 2002) and diprotonated benzene-1,3-diamine (Dobrzycki & Woźniak 2008; Imaz et al. 2007) have been observed previously.

In the title compound, (bdaH₂)[Ni(pydc)₂].5H₂O, the anionic part is comprised of a Ni^II ion which is six-coordinated by two pyridyl nitrogen and four oxygen atoms from pydc ligands. The Ni(II) ion has a distorted octahedral geometry. (Fig. 1). Bond lengths for Ni—O and Ni—N and angles (Table 1) are in normal ranges (Aghabozorg et al. 2009; Attar Gharamaleki et al. 2009; Sharif et al. 2007). Crystal packing is stabilized by intermolecular O—H···O, N—H···O and weak C—H···O intermolecular hydrogen bonds which formed between [Ni(pydc)₂]^2-, (bdaH₂)²⁺ and water molecules (Fig. 2 & Table 2). There are also π-π interactions between pyridine rings of pydc and between benzene ring of (bdaH₂)²⁺ and pyridine ring of pydc molecule by distances Cg5···Cg5^ix and Cg6···Cg7 of 3.4669 (19) and 3.764 (2) Å, respectively. [Cg5, Cg6 and Cg7 are centroids of N1/C1—C6, N2/C8—C12 and C15—C20 rings, respectively. Symmetry code: (ix) 1 - x,2 - y,2 - z]. Intermolecular π-π interactions are shown in Fig. 3.

Related literature top

For background to proton-transfer compounds, see: Aghabozorg et al. (2008). For related structures, see: Aghabozorg et al. (2009); Beatty et al. (2002); Dobrzycki & Woźniak (2008); Attar Gharamaleki et al. (2009); Imaz et al. (2007); MacDonald et al. (2000, 2004); Sharif et al. (2007).

Experimental top

A solution of pyridine-2,6-dicarboxylic acid (pydcH₂) (162 mg, 0.9 mmol) in 15 ml water was added to a solution of benzene-1,3-diamine (bda) (108 mg, 0.6 mmol) in 12 ml water and stirred for half an hour. Then a solution of NiCl₂.6H₂O (7 mg, 0.7 mmol) in 5 ml water was added to the solution of pydcH₂ and bda. The resulted solution was stirred for 2 hrs and green crystals of the title compound were obtained after one week which were suitable for X-ray analysis (m.p 200°C).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-AREA (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at 30% probability level.
	Fig. 2. Packing diagram of the title compound viewed down the a-axis. The intermolecular O—H···O, N—H···O and C—H···O hydrogen bonds are shown as blue dashed lines.
	Fig. 3. Packing diagram of the title compound viewed down the a-axis showing intermolecular π-π interactions (dashed lines). Hydrogen atoms and water molecules have been omitted for clarity.

Benzene-1,3-diammonium bis(pyridine-2,6-dicarboxylato)nickelate(II) pentahydrate top

Crystal data top

(C₆H₁₀N₂)[Ni(C₇H₃NO₄)₂]·5H₂O	F(000) = 1224.0
M_r = 589.14	D_x = 1.574 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6687 reflections
a = 7.5331 (15) Å	θ = 2.2–29.2°
b = 18.085 (4) Å	µ = 0.86 mm⁻¹
c = 18.578 (4) Å	T = 298 K
β = 100.90 (3)°	Needle, green
V = 2485.3 (9) Å³	0.2 × 0.15 × 0.1 mm
Z = 4

Data collection top

Stoe IPDS II diffractometer	6687 independent reflections
Radiation source: fine-focus sealed tube	3608 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.090
Detector resolution: 0.15 mm pixels mm^-1	θ_max = 29.2°, θ_min = 2.2°
rotation method scans	h = −10→9
Absorption correction: numerical [shape of crystal determined optically (X-RED and X-SHAPE (Stoe & Cie, 2005)]	k = −24→24
T_min = 0.855, T_max = 0.920	l = −25→25
18439 measured reflections

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 0.92	w = 1/[σ²(F_o²) + (0.0238P)²] where P = (F_o² + 2F_c²)/3
6687 reflections	(Δ/σ)_max = 0.001
407 parameters	Δρ_max = 0.39 e Å⁻³
4 restraints	Δρ_min = −0.36 e Å⁻³

Crystal data top

(C₆H₁₀N₂)[Ni(C₇H₃NO₄)₂]·5H₂O	V = 2485.3 (9) Å³
M_r = 589.14	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.5331 (15) Å	µ = 0.86 mm⁻¹
b = 18.085 (4) Å	T = 298 K
c = 18.578 (4) Å	0.2 × 0.15 × 0.1 mm
β = 100.90 (3)°

Data collection top

Stoe IPDS II diffractometer	6687 independent reflections
Absorption correction: numerical [shape of crystal determined optically (X-RED and X-SHAPE (Stoe & Cie, 2005)]	3608 reflections with I > 2σ(I)
T_min = 0.855, T_max = 0.920	R_int = 0.090
18439 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	4 restraints
wR(F²) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 0.92	Δρ_max = 0.39 e Å⁻³
6687 reflections	Δρ_min = −0.36 e Å⁻³
407 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
O12	0.0352 (4)	0.65115 (16)	0.82305 (17)	0.0522 (8)
Ni1	0.64385 (6)	0.98344 (2)	0.81233 (2)	0.02316 (10)
N1	0.6858 (3)	1.00256 (12)	0.91843 (12)	0.0203 (5)
N2	0.6146 (3)	0.96578 (13)	0.70636 (12)	0.0225 (6)
O7	0.4041 (3)	0.91734 (12)	0.79023 (11)	0.0312 (5)
O3	0.4988 (3)	1.08346 (11)	0.81671 (11)	0.0305 (5)
O5	0.8722 (3)	1.03845 (12)	0.78742 (11)	0.0368 (6)
C11	0.7284 (5)	0.97699 (19)	0.59762 (16)	0.0354 (8)
H11	0.8166	0.9944	0.5730	0.042*
C12	0.7401 (4)	0.99113 (17)	0.67087 (15)	0.0262 (7)
O1	0.8002 (3)	0.89096 (11)	0.85564 (11)	0.0315 (5)
C1	0.7845 (4)	0.95527 (15)	0.96399 (15)	0.0200 (6)
C5	0.6176 (4)	1.06446 (15)	0.94246 (15)	0.0227 (7)
N3	0.9677 (4)	0.80203 (19)	0.77250 (17)	0.0290 (6)
C3	0.7580 (4)	1.03320 (17)	1.06483 (16)	0.0277 (7)
H3	0.7827	1.0437	1.1147	0.033*
C4	0.6531 (4)	1.08166 (17)	1.01596 (16)	0.0275 (7)
H4	0.6078	1.1249	1.0328	0.033*
C2	0.8252 (4)	0.96944 (16)	1.03883 (15)	0.0272 (7)
H2	0.8960	0.9368	1.0707	0.033*
C8	0.4727 (4)	0.92723 (16)	0.67186 (16)	0.0255 (7)
C15	0.8119 (4)	0.77521 (16)	0.71966 (16)	0.0241 (7)
C7	0.5013 (4)	1.10803 (16)	0.88110 (17)	0.0256 (7)
C20	0.6666 (4)	0.74641 (17)	0.74619 (17)	0.0261 (7)
H20	0.6665	0.7454	0.7962	0.031*
C16	0.8142 (4)	0.77784 (17)	0.64577 (17)	0.0289 (7)
H16	0.9119	0.7982	0.6287	0.035*
O4	0.4185 (3)	1.16332 (11)	0.89702 (12)	0.0322 (5)
O2	0.9292 (4)	0.83930 (13)	0.96180 (12)	0.0431 (6)
O8	0.2157 (3)	0.86339 (14)	0.69685 (13)	0.0467 (7)
O6	1.0038 (3)	1.06724 (13)	0.69308 (13)	0.0468 (7)
C19	0.5220 (4)	0.71920 (16)	0.69634 (16)	0.0238 (7)
N4	0.3701 (4)	0.68770 (17)	0.72430 (17)	0.0275 (6)
C18	0.5215 (4)	0.72028 (17)	0.62201 (17)	0.0303 (8)
H18	0.4235	0.7015	0.5890	0.036*
C6	0.8438 (4)	0.88880 (17)	0.92559 (16)	0.0266 (7)
C14	0.8847 (4)	1.03584 (17)	0.72077 (17)	0.0311 (8)
C17	0.6668 (5)	0.74933 (19)	0.59727 (17)	0.0369 (8)
H17	0.6669	0.7500	0.5472	0.044*
C9	0.4516 (5)	0.91218 (18)	0.59783 (17)	0.0334 (8)
H9	0.3513	0.8863	0.5734	0.040*
C10	0.5841 (5)	0.93673 (19)	0.56106 (18)	0.0394 (9)
H10	0.5756	0.9260	0.5116	0.047*
C13	0.3517 (4)	0.90100 (17)	0.72284 (16)	0.0271 (7)
O11	0.3389 (4)	0.77842 (17)	0.84618 (15)	0.0402 (7)
O9	0.5261 (5)	0.72860 (19)	0.98420 (18)	0.0583 (9)
O10	0.8429 (5)	0.6926 (2)	0.93695 (19)	0.0649 (9)
O13	0.8277 (5)	0.9051 (2)	0.4247 (2)	0.0646 (9)
H11A	0.360 (6)	0.820 (2)	0.839 (2)	0.057 (15)*
H11B	0.381 (6)	0.765 (2)	0.8838 (19)	0.062 (15)*
H12B	0.114 (8)	0.633 (4)	0.852 (3)	0.15 (3)*
H13A	0.879 (7)	0.923 (3)	0.398 (3)	0.11 (3)*
H12A	0.025 (7)	0.627 (3)	0.781 (3)	0.103 (19)*
H9B	0.552 (7)	0.761 (3)	1.018 (3)	0.09 (2)*
H9A	0.628 (7)	0.718 (2)	0.972 (2)	0.067 (17)*
H10A	0.857 (8)	0.670 (3)	0.902 (2)	0.10 (2)*
H13B	0.894 (7)	0.873 (3)	0.446 (3)	0.08 (2)*
H10B	0.882 (7)	0.744 (3)	0.940 (3)	0.095 (18)*
H3A	1.023 (6)	0.763 (2)	0.797 (2)	0.063 (14)*
H3B	1.051 (6)	0.826 (2)	0.750 (2)	0.056 (13)*
H3C	0.932 (6)	0.834 (2)	0.805 (2)	0.061 (13)*
H4C	0.398 (5)	0.641 (2)	0.750 (2)	0.054 (12)*
H4A	0.351 (5)	0.716 (2)	0.763 (2)	0.045 (11)*
H4B	0.279 (5)	0.6851 (18)	0.6925 (19)	0.034 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O12	0.064 (2)	0.0460 (17)	0.0440 (17)	0.0030 (15)	0.0021 (16)	−0.0136 (14)
Ni1	0.0261 (2)	0.02501 (18)	0.01821 (16)	−0.0019 (2)	0.00388 (14)	−0.00170 (18)
N1	0.0188 (12)	0.0206 (14)	0.0222 (12)	−0.0019 (9)	0.0056 (10)	−0.0015 (9)
N2	0.0244 (13)	0.0238 (14)	0.0202 (12)	−0.0022 (10)	0.0065 (10)	−0.0012 (10)
O7	0.0347 (13)	0.0370 (13)	0.0238 (11)	−0.0078 (10)	0.0100 (10)	−0.0045 (9)
O3	0.0346 (13)	0.0301 (12)	0.0247 (11)	0.0043 (10)	0.0004 (10)	0.0004 (9)
O5	0.0391 (14)	0.0434 (14)	0.0279 (11)	−0.0156 (11)	0.0059 (10)	−0.0076 (10)
C11	0.047 (2)	0.0370 (18)	0.0253 (15)	−0.0073 (18)	0.0145 (14)	−0.0003 (15)
C12	0.0315 (16)	0.0238 (16)	0.0247 (14)	−0.0044 (14)	0.0087 (12)	0.0014 (13)
O1	0.0398 (14)	0.0310 (12)	0.0236 (11)	0.0110 (10)	0.0055 (10)	−0.0036 (9)
C1	0.0137 (14)	0.0242 (15)	0.0232 (14)	−0.0027 (12)	0.0065 (12)	0.0009 (12)
C5	0.0205 (15)	0.0215 (15)	0.0259 (15)	−0.0013 (12)	0.0037 (13)	0.0000 (12)
N3	0.0201 (15)	0.0389 (18)	0.0281 (15)	−0.0029 (14)	0.0049 (13)	−0.0087 (14)
C3	0.0271 (16)	0.0371 (19)	0.0194 (14)	−0.0066 (14)	0.0055 (13)	−0.0057 (12)
C4	0.0247 (16)	0.0303 (17)	0.0298 (16)	−0.0002 (13)	0.0108 (13)	−0.0110 (13)
C2	0.0287 (16)	0.0288 (18)	0.0222 (14)	−0.0009 (13)	0.0003 (13)	0.0027 (12)
C8	0.0308 (18)	0.0221 (15)	0.0228 (15)	−0.0016 (13)	0.0033 (13)	0.0001 (12)
C15	0.0191 (15)	0.0245 (16)	0.0275 (16)	0.0021 (13)	0.0013 (13)	−0.0072 (13)
C7	0.0231 (16)	0.0222 (16)	0.0300 (17)	−0.0034 (13)	0.0012 (13)	−0.0005 (13)
C20	0.0230 (16)	0.0331 (17)	0.0223 (15)	−0.0011 (14)	0.0045 (13)	−0.0028 (13)
C16	0.0272 (17)	0.0323 (18)	0.0291 (17)	−0.0044 (14)	0.0102 (14)	−0.0026 (14)
O4	0.0273 (12)	0.0288 (12)	0.0397 (13)	0.0071 (10)	0.0046 (10)	−0.0025 (10)
O2	0.0580 (17)	0.0336 (13)	0.0354 (13)	0.0184 (12)	0.0028 (12)	0.0041 (10)
O8	0.0359 (15)	0.0651 (17)	0.0383 (14)	−0.0234 (13)	0.0050 (12)	−0.0055 (12)
O6	0.0472 (16)	0.0525 (16)	0.0451 (15)	−0.0244 (13)	0.0199 (12)	−0.0063 (12)
C19	0.0195 (15)	0.0224 (15)	0.0298 (16)	0.0021 (12)	0.0055 (13)	−0.0021 (13)
N4	0.0202 (15)	0.0293 (16)	0.0323 (16)	−0.0033 (12)	0.0029 (13)	−0.0012 (13)
C18	0.0294 (18)	0.0313 (18)	0.0282 (16)	−0.0047 (14)	0.0001 (14)	−0.0062 (13)
C6	0.0266 (17)	0.0269 (17)	0.0266 (16)	−0.0008 (14)	0.0056 (14)	−0.0010 (13)
C14	0.0299 (18)	0.0325 (19)	0.0337 (17)	−0.0066 (14)	0.0132 (14)	−0.0037 (14)
C17	0.042 (2)	0.047 (2)	0.0215 (16)	−0.0046 (17)	0.0054 (16)	−0.0021 (15)
C9	0.036 (2)	0.0371 (19)	0.0248 (16)	−0.0068 (15)	0.0012 (15)	−0.0032 (14)
C10	0.054 (2)	0.044 (2)	0.0226 (17)	−0.0075 (18)	0.0128 (16)	−0.0024 (15)
C13	0.0239 (17)	0.0287 (17)	0.0299 (17)	−0.0004 (14)	0.0082 (14)	0.0003 (13)
O11	0.0474 (17)	0.0362 (16)	0.0357 (16)	−0.0017 (13)	0.0051 (13)	0.0008 (13)
O9	0.059 (2)	0.068 (2)	0.0464 (19)	0.0053 (18)	0.0066 (17)	−0.0100 (16)
O10	0.077 (2)	0.058 (2)	0.063 (2)	0.0039 (18)	0.0247 (18)	−0.0084 (18)
O13	0.060 (2)	0.082 (3)	0.059 (2)	−0.001 (2)	0.0275 (19)	0.0045 (19)

Geometric parameters (Å, º) top

O12—H12B	0.79 (4)	C2—H2	0.9300
O12—H12A	0.89 (6)	C8—C9	1.381 (4)
Ni1—N2	1.965 (2)	C8—C13	1.510 (5)
Ni1—N1	1.967 (2)	C15—C16	1.377 (4)
Ni1—O5	2.113 (2)	C15—C20	1.384 (4)
Ni1—O1	2.115 (2)	C7—O4	1.244 (4)
Ni1—O3	2.123 (2)	C20—C19	1.380 (4)
Ni1—O7	2.140 (2)	C20—H20	0.9300
N1—C1	1.328 (3)	C16—C17	1.390 (4)
N1—C5	1.343 (4)	C16—H16	0.9300
N2—C12	1.332 (4)	O2—C6	1.226 (3)
N2—C8	1.334 (4)	O8—C13	1.248 (4)
O7—C13	1.274 (3)	O6—C14	1.251 (4)
O3—C7	1.273 (4)	C19—C18	1.381 (4)
O5—C14	1.260 (4)	C19—N4	1.459 (4)
C11—C12	1.371 (4)	N4—H4C	0.97 (4)
C11—C10	1.376 (5)	N4—H4A	0.91 (4)
C11—H11	0.9300	N4—H4B	0.82 (3)
C12—C14	1.522 (4)	C18—C17	1.370 (5)
O1—C6	1.279 (3)	C18—H18	0.9300
C1—C2	1.390 (4)	C17—H17	0.9300
C1—C6	1.508 (4)	C9—C10	1.385 (5)
C5—C4	1.376 (4)	C9—H9	0.9300
C5—C7	1.520 (4)	C10—H10	0.9300
N3—C15	1.463 (4)	O11—H11A	0.79 (4)
N3—H3A	0.91 (4)	O11—H11B	0.75 (3)
N3—H3B	0.93 (5)	O9—H9B	0.85 (5)
N3—H3C	0.91 (5)	O9—H9A	0.86 (5)
C3—C2	1.383 (4)	O10—H10A	0.79 (3)
C3—C4	1.395 (4)	O10—H10B	0.97 (5)
C3—H3	0.9300	O13—H13A	0.76 (4)
C4—H4	0.9300	O13—H13B	0.82 (5)

H12B—O12—H12A	109 (6)	C3—C2—H2	120.7
N2—Ni1—N1	177.13 (11)	C1—C2—H2	120.7
N2—Ni1—O5	78.39 (10)	N2—C8—C9	120.8 (3)
N1—Ni1—O5	98.84 (9)	N2—C8—C13	112.7 (3)
N2—Ni1—O1	101.62 (9)	C9—C8—C13	126.4 (3)
N1—Ni1—O1	77.61 (9)	C16—C15—C20	121.9 (3)
O5—Ni1—O1	92.17 (9)	C16—C15—N3	119.8 (3)
N2—Ni1—O3	102.47 (9)	C20—C15—N3	118.3 (3)
N1—Ni1—O3	78.34 (9)	O4—C7—O3	125.8 (3)
O5—Ni1—O3	93.06 (9)	O4—C7—C5	118.9 (3)
O1—Ni1—O3	155.91 (8)	O3—C7—C5	115.3 (3)
N2—Ni1—O7	77.66 (10)	C19—C20—C15	118.2 (3)
N1—Ni1—O7	105.08 (9)	C19—C20—H20	120.9
O5—Ni1—O7	156.01 (8)	C15—C20—H20	120.9
O1—Ni1—O7	91.16 (9)	C15—C16—C17	118.3 (3)
O3—Ni1—O7	93.54 (9)	C15—C16—H16	120.8
C1—N1—C5	121.9 (2)	C17—C16—H16	120.8
C1—N1—Ni1	119.34 (19)	C20—C19—C18	121.2 (3)
C5—N1—Ni1	118.74 (18)	C20—C19—N4	118.2 (3)
C12—N2—C8	121.4 (3)	C18—C19—N4	120.5 (3)
C12—N2—Ni1	118.97 (19)	C19—N4—H4C	114 (2)
C8—N2—Ni1	119.6 (2)	C19—N4—H4A	108 (2)
C13—O7—Ni1	114.3 (2)	H4C—N4—H4A	99 (3)
C7—O3—Ni1	114.67 (18)	C19—N4—H4B	112 (3)
C14—O5—Ni1	114.38 (19)	H4C—N4—H4B	112 (3)
C12—C11—C10	119.0 (3)	H4A—N4—H4B	111 (3)
C12—C11—H11	120.5	C17—C18—C19	119.3 (3)
C10—C11—H11	120.5	C17—C18—H18	120.3
N2—C12—C11	120.6 (3)	C19—C18—H18	120.3
N2—C12—C14	112.0 (2)	O2—C6—O1	125.9 (3)
C11—C12—C14	127.4 (3)	O2—C6—C1	119.6 (3)
C6—O1—Ni1	115.35 (19)	O1—C6—C1	114.5 (3)
N1—C1—C2	120.7 (3)	O6—C14—O5	125.4 (3)
N1—C1—C6	113.1 (2)	O6—C14—C12	118.5 (3)
C2—C1—C6	126.2 (3)	O5—C14—C12	116.1 (3)
N1—C5—C4	120.3 (3)	C18—C17—C16	121.1 (3)
N1—C5—C7	112.7 (2)	C18—C17—H17	119.5
C4—C5—C7	127.1 (3)	C16—C17—H17	119.5
C15—N3—H3A	108 (3)	C8—C9—C10	118.0 (3)
C15—N3—H3B	112 (2)	C8—C9—H9	121.0
H3A—N3—H3B	108 (4)	C10—C9—H9	121.0
C15—N3—H3C	111 (3)	C11—C10—C9	120.1 (3)
H3A—N3—H3C	109 (4)	C11—C10—H10	119.9
H3B—N3—H3C	109 (4)	C9—C10—H10	119.9
C2—C3—C4	119.8 (3)	O8—C13—O7	125.8 (3)
C2—C3—H3	120.1	O8—C13—C8	118.5 (3)
C4—C3—H3	120.1	O7—C13—C8	115.6 (3)
C5—C4—C3	118.9 (3)	H11A—O11—H11B	113 (4)
C5—C4—H4	120.6	H9B—O9—H9A	105 (5)
C3—C4—H4	120.6	H10A—O10—H10B	117 (6)
C3—C2—C1	118.5 (3)	H13A—O13—H13B	106 (6)

N2—Ni1—N1—C1	−74 (2)	Ni1—N1—C5—C4	−176.3 (2)
O5—Ni1—N1—C1	−89.1 (2)	C1—N1—C5—C7	−177.0 (3)
O1—Ni1—N1—C1	1.2 (2)	Ni1—N1—C5—C7	4.9 (3)
O3—Ni1—N1—C1	179.6 (2)	N1—C5—C4—C3	−1.0 (5)
O7—Ni1—N1—C1	89.0 (2)	C7—C5—C4—C3	177.5 (3)
N2—Ni1—N1—C5	104 (2)	C2—C3—C4—C5	0.4 (5)
O5—Ni1—N1—C5	89.0 (2)	C4—C3—C2—C1	−0.4 (5)
O1—Ni1—N1—C5	179.3 (2)	N1—C1—C2—C3	1.1 (4)
O3—Ni1—N1—C5	−2.3 (2)	C6—C1—C2—C3	−179.5 (3)
O7—Ni1—N1—C5	−92.9 (2)	C12—N2—C8—C9	0.2 (4)
N1—Ni1—N2—C12	−14 (2)	Ni1—N2—C8—C9	−178.1 (2)
O5—Ni1—N2—C12	2.1 (2)	C12—N2—C8—C13	177.5 (3)
O1—Ni1—N2—C12	−87.8 (2)	Ni1—N2—C8—C13	−0.8 (3)
O3—Ni1—N2—C12	92.7 (2)	Ni1—O3—C7—O4	−176.1 (3)
O7—Ni1—N2—C12	−176.4 (2)	Ni1—O3—C7—C5	4.0 (3)
N1—Ni1—N2—C8	164.8 (19)	N1—C5—C7—O4	174.2 (3)
O5—Ni1—N2—C8	−179.6 (2)	C4—C5—C7—O4	−4.4 (5)
O1—Ni1—N2—C8	90.5 (2)	N1—C5—C7—O3	−5.9 (4)
O3—Ni1—N2—C8	−89.0 (2)	C4—C5—C7—O3	175.5 (3)
O7—Ni1—N2—C8	1.9 (2)	C16—C15—C20—C19	0.6 (5)
N2—Ni1—O7—C13	−2.9 (2)	N3—C15—C20—C19	−178.2 (3)
N1—Ni1—O7—C13	178.0 (2)	C20—C15—C16—C17	−1.2 (5)
O5—Ni1—O7—C13	−6.6 (3)	N3—C15—C16—C17	177.6 (3)
O1—Ni1—O7—C13	−104.5 (2)	C15—C20—C19—C18	0.2 (4)
O3—Ni1—O7—C13	99.1 (2)	C15—C20—C19—N4	179.0 (3)
N2—Ni1—O3—C7	−178.4 (2)	C20—C19—C18—C17	−0.4 (5)
N1—Ni1—O3—C7	−1.2 (2)	N4—C19—C18—C17	−179.2 (3)
O5—Ni1—O3—C7	−99.6 (2)	Ni1—O1—C6—O2	177.8 (3)
O1—Ni1—O3—C7	2.7 (4)	Ni1—O1—C6—C1	−3.4 (3)
O7—Ni1—O3—C7	103.5 (2)	N1—C1—C6—O2	−176.8 (3)
N2—Ni1—O5—C14	0.6 (2)	C2—C1—C6—O2	3.7 (5)
N1—Ni1—O5—C14	179.8 (2)	N1—C1—C6—O1	4.4 (4)
O1—Ni1—O5—C14	102.0 (2)	C2—C1—C6—O1	−175.1 (3)
O3—Ni1—O5—C14	−101.6 (2)	Ni1—O5—C14—O6	176.6 (3)
O7—Ni1—O5—C14	4.2 (4)	Ni1—O5—C14—C12	−2.7 (3)
C8—N2—C12—C11	−1.2 (4)	N2—C12—C14—O6	−175.0 (3)
Ni1—N2—C12—C11	177.1 (2)	C11—C12—C14—O6	3.9 (5)
C8—N2—C12—C14	177.8 (3)	N2—C12—C14—O5	4.3 (4)
Ni1—N2—C12—C14	−3.9 (3)	C11—C12—C14—O5	−176.7 (3)
C10—C11—C12—N2	0.6 (5)	C19—C18—C17—C16	−0.2 (5)
C10—C11—C12—C14	−178.3 (3)	C15—C16—C17—C18	0.9 (5)
N2—Ni1—O1—C6	178.6 (2)	N2—C8—C9—C10	1.5 (5)
N1—Ni1—O1—C6	1.5 (2)	C13—C8—C9—C10	−175.4 (3)
O5—Ni1—O1—C6	100.0 (2)	C12—C11—C10—C9	1.1 (5)
O3—Ni1—O1—C6	−2.4 (4)	C8—C9—C10—C11	−2.1 (5)
O7—Ni1—O1—C6	−103.7 (2)	Ni1—O7—C13—O8	−179.7 (3)
C5—N1—C1—C2	−1.8 (4)	Ni1—O7—C13—C8	3.3 (3)
Ni1—N1—C1—C2	176.3 (2)	N2—C8—C13—O8	−179.0 (3)
C5—N1—C1—C6	178.8 (3)	C9—C8—C13—O8	−1.9 (5)
Ni1—N1—C1—C6	−3.2 (3)	N2—C8—C13—O7	−1.8 (4)
C1—N1—C5—C4	1.7 (4)	C9—C8—C13—O7	175.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O2ⁱ	0.93	2.48	3.118 (4)	126
C3—H3···O7ⁱⁱ	0.93	2.56	3.284 (4)	135
O13—H13B···O9ⁱⁱⁱ	0.82 (5)	2.14 (5)	2.945 (6)	166 (5)
O13—H13A···O6^iv	0.76 (4)	2.05 (4)	2.776 (5)	158 (6)
O12—H12B···O13^v	0.79 (4)	2.02 (4)	2.808 (5)	176 (8)
O12—H12A···O3^vi	0.89 (6)	1.95 (6)	2.838 (4)	174 (5)
O11—H11B···O9	0.75 (3)	2.08 (3)	2.829 (4)	173 (5)
O11—H11A···O7	0.79 (4)	2.03 (4)	2.798 (4)	163 (4)
O10—H10B···O2	0.97 (5)	1.80 (5)	2.750 (4)	168 (5)
O10—H10A···O12^vii	0.79 (3)	2.20 (5)	2.880 (5)	146 (6)
O9—H9B···O4ⁱⁱ	0.85 (5)	2.07 (5)	2.918 (4)	172 (5)
O9—H9A···O10	0.86 (5)	1.91 (5)	2.772 (5)	176 (4)
N4—H4C···O6^viii	0.97 (4)	1.78 (4)	2.730 (4)	167 (3)
N4—H4B···O4^vi	0.82 (3)	2.05 (4)	2.854 (4)	168 (3)
N4—H4A···O11	0.91 (4)	1.94 (4)	2.842 (4)	173 (3)
N3—H3C···O1	0.91 (5)	1.82 (5)	2.702 (4)	164 (4)
N3—H3B···O8^vii	0.93 (5)	1.85 (5)	2.773 (4)	173 (4)
N3—H3A···O12^vii	0.91 (4)	2.07 (4)	2.899 (5)	152 (4)

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

Experimental details

Crystal data
Chemical formula	(C₆H₁₀N₂)[Ni(C₇H₃NO₄)₂]·5H₂O
M_r	589.14
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	7.5331 (15), 18.085 (4), 18.578 (4)
β (°)	100.90 (3)
V (Å³)	2485.3 (9)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.86
Crystal size (mm)	0.2 × 0.15 × 0.1

Data collection
Diffractometer	Stoe IPDS II diffractometer
Absorption correction	Numerical [shape of crystal determined optically (X-RED and X-SHAPE (Stoe & Cie, 2005)]
T_min, T_max	0.855, 0.920
No. of measured, independent and observed [I > 2σ(I)] reflections	18439, 6687, 3608
R_int	0.090
(sin θ/λ)_max (Å⁻¹)	0.687

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.086, 0.92
No. of reflections	6687
No. of parameters	407
No. of restraints	4
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.36

Computer programs: X-AREA (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18···O2ⁱ	0.93	2.48	3.118 (4)	125.5
C3—H3···O7ⁱⁱ	0.93	2.56	3.284 (4)	135.4
O13—H13B···O9ⁱⁱⁱ	0.82 (5)	2.14 (5)	2.945 (6)	166 (5)
O13—H13A···O6^iv	0.76 (4)	2.05 (4)	2.776 (5)	158 (6)
O12—H12B···O13^v	0.79 (4)	2.02 (4)	2.808 (5)	176 (8)
O12—H12A···O3^vi	0.89 (6)	1.95 (6)	2.838 (4)	174 (5)
O11—H11B···O9	0.75 (3)	2.08 (3)	2.829 (4)	173 (5)
O11—H11A···O7	0.79 (4)	2.03 (4)	2.798 (4)	163 (4)
O10—H10B···O2	0.97 (5)	1.80 (5)	2.750 (4)	168 (5)
O10—H10A···O12^vii	0.79 (3)	2.20 (5)	2.880 (5)	146 (6)
O9—H9B···O4ⁱⁱ	0.85 (5)	2.07 (5)	2.918 (4)	172 (5)
O9—H9A···O10	0.86 (5)	1.91 (5)	2.772 (5)	176 (4)
N4—H4C···O6^viii	0.97 (4)	1.78 (4)	2.730 (4)	167 (3)
N4—H4B···O4^vi	0.82 (3)	2.05 (4)	2.854 (4)	168 (3)
N4—H4A···O11	0.91 (4)	1.94 (4)	2.842 (4)	173 (3)
N3—H3C···O1	0.91 (5)	1.82 (5)	2.702 (4)	164 (4)
N3—H3B···O8^vii	0.93 (5)	1.85 (5)	2.773 (4)	173 (4)
N3—H3A···O12^vii	0.91 (4)	2.07 (4)	2.899 (5)	152 (4)

Acknowledgements

The authors are grateful to the Islamic Azad University, North Branch, for financial support of this work.

References

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Volume 67| Part 2| February 2011| Pages m193-m194

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metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Benzene-1,3-di­ammonium bis­­(pyridine-2,6-di­carboxyl­ato)nickelate(II) penta­hydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Benzene-1,3-diammonium bis(pyridine-2,6-dicarboxylato)nickelate(II) pentahydrate