Bis(2,6-diamino­pyridinium) bis­(pyridine-2,6-dicarboxyl­ato)zincate(II) monohydrate

Tabatabaee, M.; Tahriri, M.; Tahriri, M.; Dušek, M.; Fejfarová, K.

doi:10.1107/S1600536811018204

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 6| June 2011| Pages m769-m770

doi:10.1107/S1600536811018204

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Bis(2,6-diaminopyridinium) bis(pyridine-2,6-dicarboxylato)zincate(II) monohydrate

Masoumeh Tabatabaee,^a ^* Marjan Tahriri,^a Mozhgan Tahriri,^a Michal Dušek ^b and Karla Fejfarová ^b

^aDepartment of Chemistry,Yazd Branch, Islamic Azad University, Yazd, Iran, and ^bInstitute of Physics ASCR, v.v.i., Na Slovance 2, 182 21 Praha 8, Czech Republic
^*Correspondence e-mail: tabatabaee45m@yahoo.com

(Received 10 May 2011; accepted 13 May 2011; online 20 May 2011)

In the title hydrated molecular salt, (C₅H₈N₃)₂[Zn(C₇H₃NO₄)₂]·H₂O, the Zn^II atom is coordinated by two O,N,O′-tridentate pyridine-2,6-dicarboxylate dianions, generating a slightly distorted trans-ZnN₂O₄ octahedral coordination geometry for the metal ion. In the crystal, a network of O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds involving the cations, anions and water molecules results in a three-dimensional network.

Related literature

For isostructural molecular salts with Co and Ni, see: Moghimi et al. (2002a ,b ). For related sturctures, see: Tabatabaee et al. (2009 ); Ranjbar et al. (2002 ); Moghimi et al. (2005 ).

Experimental

Crystal data

(C₅H₈N₃)₂[Zn(C₇H₃NO₄)₂]·H₂O
M_r = 633.9
Monoclinic, P 2₁ /c
a = 8.2940 (3) Å
b = 13.2368 (4) Å
c = 23.8063 (7) Å
β = 104.995 (3)°
V = 2524.60 (14) Å³
Z = 4
Cu Kα radiation
μ = 1.99 mm⁻¹
T = 120 K
0.26 × 0.19 × 0.10 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Oxfordshire, England.]$ ) T_min = 0.142, T_max = 1
66673 measured reflections
4502 independent reflections
4175 reflections with I > 3σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.024
wR(F²) = 0.077
S = 1.61
4502 reflections
415 parameters
12 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Selected bond lengths (Å)

Zn1—O1	2.1725 (10)
Zn1—O3	2.1886 (11)
Zn1—O5	2.2595 (9)
Zn1—O7	2.2372 (8)
Zn1—N1	2.0107 (11)
Zn1—N2	2.0001 (11)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C10—H10⋯O3ⁱ	0.96	2.49	3.1769 (16)	129
C18—H18⋯O4	0.96	2.59	3.3556 (16)	137
C22—H22⋯O3ⁱⁱ	0.96	2.59	3.3789 (17)	139
N3—H3n⋯O8ⁱⁱ	0.854 (13)	1.948 (13)	2.7845 (13)	166.0 (16)
N4—H4n⋯O4ⁱⁱⁱ	0.845 (17)	2.096 (17)	2.9287 (16)	168.4 (14)
N4—H4m⋯O7ⁱⁱ	0.838 (14)	2.357 (14)	3.1874 (14)	171.0 (17)
N5—H5n⋯O4	0.878 (15)	2.206 (14)	3.0600 (14)	164.2 (15)
N5—H5m⋯O9^iv	0.872 (15)	2.066 (15)	2.9203 (15)	166.3 (17)
N6—H6n⋯O6^v	0.884 (14)	1.763 (14)	2.6381 (13)	169.9 (15)
N7—H7n⋯O2^vi	0.866 (15)	2.032 (15)	2.8818 (15)	166.8 (17)
N8—H8n⋯O2^vii	0.840 (18)	2.085 (18)	2.9206 (17)	172.4 (17)
O9—H9o⋯O1^v	0.83 (2)	2.06 (2)	2.8936 (14)	174 (2)
O9—H9p⋯O8^viii	0.866 (19)	1.928 (19)	2.7462 (14)	157.1 (18)
Symmetry codes: (i) -x+1, -y, -z+1; (ii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iv) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (v) -x+1, -y+1, -z+1; (vi) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (vii) -x+2, -y+1, -z+1; (viii) x-1, y+1, z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Oxfordshire, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR2002 (Burla et al., 2003 ); program(s) used to refine structure: JANA2006 (Petříček et al., 2007); molecular graphics: DIAMOND (Brandenburg & Putz, 2005 ); software used to prepare material for publication: JANA2006.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811018204/hb5879sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811018204/hb5879Isup2.hkl

checkCIF report

Comment top

The title compound, (I), consists of a [Zn(pydc)₂]^2- dianion, two (pydaH)⁺ cations and one uncoordinated water molecule (Fig. 1) (pydcH₂ = pyridine-2,6-dicarboxylic acid; pyda = 2,6-diaminopyridine), and is isostructural with Co (Moghimi et al. 2002a) and Ni (Moghimi et al. 2002b) compounds. Zn^II atom in the title compound is six-coordinated by two (pydc)^2– anions and the geometry of the resulting ZnN2O4 coordination can be described as distorted octahedral. The N atoms occupy the axial positions. The N1—Zn1—N2 angle (175.74 (5)°) deviates from linearity. The dihedral angle between the mean planes of the pyridine rings (A1 and A2, defined in Fig. 1) is 75.24 (6)°. Zn—N distances of (2.0011 (16) and 2.0107 (11) Å and Zn—O distances (Zn1—O1: 2.1725 (10), Zn1—O3: 2.1886 (11), Zn1—O5: 2.2595 (9) and Zn1—O7: 2.2372 (8) Å) are consistent with those found in (acrH)[Zn(pydc)(pydcH)].5H₂O (Tabatabaee et al. 2009), (pydaH)[Zn(pydc)(pydcH)]. 3H₂O (Ranjbar et al.. 2002) and(creatH)[Zn(pydc)(pydcH)]. 4H₂O (Moghimi et al. 2005). There are some hydrogen bonding interactions such as O—H···O, N—H···O and C—H···O between cations, anions and uncoordinated water molecule (Fig 2, Table 1). As it is seen in Fig. 3, there are also π-π stacking interactions between the aromatic rings with centroid-centroiddistances of 3.5813 (8) Åfor Cg6···Cg6 (defined by atoms N2/C8 /C12, symmetry code: (2 - x,-y,1 - z) and 3.6421 (8) Å for Cg7···Cg8 (Cg7: N3/C15—C19 and Cg8:N6/ C20—C24, symmetry code: x, y, z).Ion pairing, hydrogen bonding, π–π stacking and van der Waals interactions are also effective for packingof the crystal structure. These interactions lead to formation of a three-dimensional supramolecular structure.

Related literature top

For isostructural molecular salts with Co and Ni, see: Moghimi et al. (2002a,b). For related sturctures, see: Tabatabaee et al. (2009); Ranjbar et al. (2002); Moghimi et al. (2005).

Experimental top

An aqueous solution of ZnSO₄.7H₂O, (0.288 g, 1 mmol) in water (10 ml) was added to a stirring solution of (20 ml)pyridine-2,6-dicarboxylic acid (0.167 g, 1 mmol) and 2,6-diaminopyridine (0.11 g, 1 mmol). The reaction mixture was stirred at 298 K for 3 h. Colorless blocks of (I) were obtained after few days at 277 K.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SIR2002 (Burla et al., 2003); program(s) used to refine structure: JANA2006 (Petříček et al., 2007); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: JANA2006 (Petříček et al., 2007).

Figures top

	Fig. 1. A view of (I), with displacement ellipsoids drawn at the 50% probability level.
	Fig. 2. fragment of crystal packing. The strongest N—H···O and O—H···O interactions(with H···A distance up to 2.1 Å) interconnect all molecules of the structureinto three-dimensional network.
	Fig. 3. Representation π-π stacking between aromatic rings.

Bis(2,6-diaminopyridinium) bis(pyridine-2,6-dicarboxylato)zincate(II) monohydrate top

Crystal data top

(C₅H₈N₃)₂[Zn(C₇H₃NO₄)₂]·H₂O	F(000) = 1304
M_r = 633.9	D_x = 1.667 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.5418 Å
Hall symbol: -P 2ybc	Cell parameters from 46751 reflections
a = 8.2940 (3) Å	θ = 3.3–67.0°
b = 13.2368 (4) Å	µ = 1.99 mm⁻¹
c = 23.8063 (7) Å	T = 120 K
β = 104.995 (3)°	Block, colourless
V = 2524.60 (14) Å³	0.26 × 0.19 × 0.10 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector	4502 independent reflections
Radiation source: Enhance Ultra (Cu) X-ray Source	4175 reflections with I > 3σ(I)
Mirror monochromator	R_int = 0.031
Detector resolution: 10.3784 pixels mm^-1	θ_max = 67.1°, θ_min = 3.8°
Rotation method data acquisition using ω scans	h = −9→9
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −15→15
T_min = 0.142, T_max = 1	l = −28→28
66673 measured reflections

Refinement top

Refinement on F²	60 constraints
R[F² > 2σ(F²)] = 0.024	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.077	Weighting scheme based on measured s.u.'s w = 1/[σ²(I) + 0.0016I²]
S = 1.61	(Δ/σ)_max = 0.002
4502 reflections	Δρ_max = 0.20 e Å⁻³
415 parameters	Δρ_min = −0.32 e Å⁻³
12 restraints

Crystal data top

(C₅H₈N₃)₂[Zn(C₇H₃NO₄)₂]·H₂O	V = 2524.60 (14) Å³
M_r = 633.9	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 8.2940 (3) Å	µ = 1.99 mm⁻¹
b = 13.2368 (4) Å	T = 120 K
c = 23.8063 (7) Å	0.26 × 0.19 × 0.10 mm
β = 104.995 (3)°

Data collection top

Oxford Diffraction Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector	4502 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	4175 reflections with I > 3σ(I)
T_min = 0.142, T_max = 1	R_int = 0.031
66673 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	12 restraints
wR(F²) = 0.077	H atoms treated by a mixture of independent and constrained refinement
S = 1.61	Δρ_max = 0.20 e Å⁻³
4502 reflections	Δρ_min = −0.32 e Å⁻³
415 parameters

Special details top

Experimental. CrysAlisPro, Oxford Diffraction (2009), Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

Refinement. The refinement was carried out against all reflections. The conventional R-factor is always based on F. The goodness of fit as well as the weighted R-factor are based on F and F² for refinement carried out on F and F², respectively. The threshold expression is used only for calculating R-factors etc. and it is not relevant to the choice of reflections for refinement.

The program used for refinement, Jana2006, uses the weighting scheme based on the experimental expectations, see _refine_ls_weighting_details, that does not force S to be one. Therefore the values of S are usually larger than the ones from the SHELX program.

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

	x	y	z	U_iso*/U_eq
Zn1	0.73417 (2)	0.251250 (11)	0.490469 (7)	0.01551 (8)
O1	0.85536 (12)	0.30784 (7)	0.42606 (4)	0.0190 (3)
O2	0.90680 (12)	0.45264 (7)	0.38497 (4)	0.0203 (3)
O3	0.61404 (12)	0.27022 (7)	0.56153 (4)	0.0175 (3)
O4	0.56144 (12)	0.38883 (7)	0.62210 (4)	0.0185 (3)
O5	0.49822 (12)	0.22838 (7)	0.41879 (4)	0.0194 (3)
O6	0.38232 (13)	0.10376 (7)	0.35720 (4)	0.0266 (3)
O7	0.96377 (11)	0.19455 (7)	0.55438 (4)	0.0182 (3)
O8	1.05526 (12)	0.05147 (7)	0.60233 (4)	0.0213 (3)
N1	0.73813 (13)	0.40157 (8)	0.50291 (5)	0.0140 (3)
N2	0.71778 (13)	0.10107 (8)	0.48158 (4)	0.0141 (3)
N3	0.69954 (14)	0.60578 (8)	0.79837 (5)	0.0165 (3)
N4	0.67598 (16)	0.73531 (9)	0.86105 (5)	0.0197 (4)
N5	0.74582 (15)	0.47174 (9)	0.74142 (5)	0.0222 (4)
N6	0.84303 (14)	0.80163 (8)	0.72445 (5)	0.0165 (3)
N7	0.78444 (15)	0.93207 (9)	0.77987 (5)	0.0230 (4)
N8	0.87253 (16)	0.67785 (9)	0.66049 (5)	0.0229 (4)
C1	0.79561 (15)	0.46127 (9)	0.46716 (5)	0.0149 (4)
C2	0.79764 (16)	0.56544 (10)	0.47355 (5)	0.0174 (4)
C3	0.73738 (16)	0.60625 (10)	0.51793 (6)	0.0179 (4)
C4	0.67565 (15)	0.54303 (10)	0.55434 (5)	0.0165 (4)
C5	0.67867 (15)	0.44000 (9)	0.54554 (5)	0.0143 (4)
C6	0.85813 (15)	0.40324 (10)	0.42179 (5)	0.0163 (4)
C7	0.61279 (15)	0.35991 (9)	0.58001 (5)	0.0145 (4)
C8	0.59296 (16)	0.06081 (9)	0.44044 (5)	0.0151 (4)
C9	0.56638 (16)	−0.04242 (10)	0.43691 (5)	0.0170 (4)
C10	0.66832 (16)	−0.10379 (10)	0.47856 (6)	0.0180 (4)
C11	0.79717 (16)	−0.06116 (10)	0.52144 (6)	0.0169 (4)
C12	0.82002 (16)	0.04249 (10)	0.52096 (5)	0.0145 (4)
C13	0.48221 (16)	0.13793 (10)	0.40166 (5)	0.0173 (4)
C14	0.95791 (16)	0.10108 (10)	0.56312 (5)	0.0162 (4)
C15	0.62074 (16)	0.69111 (10)	0.80890 (5)	0.0169 (4)
C16	0.48878 (17)	0.72880 (11)	0.76506 (6)	0.0204 (4)
C17	0.44414 (17)	0.67788 (10)	0.71250 (6)	0.0222 (4)
C18	0.52517 (17)	0.59131 (10)	0.70276 (6)	0.0200 (4)
C19	0.65634 (16)	0.55427 (10)	0.74686 (5)	0.0170 (4)
C20	0.88001 (16)	0.85182 (10)	0.77596 (5)	0.0170 (4)
C21	1.01211 (17)	0.81712 (10)	0.82058 (6)	0.0197 (4)
C22	1.09920 (18)	0.73294 (11)	0.81063 (6)	0.0219 (4)
C23	1.05885 (17)	0.68247 (10)	0.75763 (6)	0.0214 (4)
C24	0.92679 (17)	0.71923 (11)	0.71358 (6)	0.0179 (4)
O9	0.13470 (16)	0.86262 (8)	0.64907 (5)	0.0345 (4)
H2	0.839584	0.608225	0.447989	0.0209*
H3	0.738256	0.678095	0.523516	0.0215*
H4	0.632137	0.570423	0.584768	0.0198*
H9	0.479364	−0.070943	0.406331	0.0204*
H10	0.65006	−0.175446	0.477824	0.0216*
H11	0.868503	−0.102603	0.550646	0.0203*
H16	0.430228	0.788661	0.771181	0.0245*
H17	0.354128	0.703644	0.681951	0.0266*
H18	0.491551	0.557035	0.666037	0.024*
H21	1.04204	0.850964	0.857491	0.0236*
H22	1.190356	0.708568	0.841236	0.0263*
H23	1.120325	0.623848	0.751528	0.0257*
H3n	0.7811 (18)	0.5828 (12)	0.8249 (6)	0.0199*
H4n	0.619 (2)	0.7832 (12)	0.8695 (7)	0.0237*
H4m	0.7661 (19)	0.7184 (14)	0.8843 (7)	0.0237*
H5n	0.711 (2)	0.4411 (13)	0.7078 (6)	0.0267*
H5m	0.798 (2)	0.4391 (13)	0.7727 (7)	0.0267*
H6n	0.7610 (18)	0.8265 (12)	0.6964 (6)	0.0198*
H7n	0.805 (2)	0.9661 (13)	0.8120 (6)	0.0276*
H7m	0.701 (2)	0.9456 (14)	0.7516 (7)	0.0276*
H8n	0.933 (2)	0.6358 (12)	0.6492 (7)	0.0275*
H8m	0.787 (2)	0.7089 (14)	0.6359 (7)	0.0275*
H9o	0.130 (3)	0.8128 (14)	0.6273 (9)	0.0517*
H9p	0.100 (3)	0.9126 (14)	0.6256 (9)	0.0517*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.02022 (13)	0.00980 (13)	0.01659 (13)	−0.00032 (6)	0.00492 (9)	−0.00079 (5)
O1	0.0250 (5)	0.0150 (4)	0.0187 (4)	−0.0002 (4)	0.0087 (4)	−0.0008 (3)
O2	0.0226 (5)	0.0217 (5)	0.0178 (4)	0.0023 (4)	0.0075 (4)	0.0046 (4)
O3	0.0208 (5)	0.0134 (4)	0.0190 (5)	−0.0020 (4)	0.0066 (4)	−0.0013 (3)
O4	0.0212 (5)	0.0190 (5)	0.0163 (4)	−0.0019 (4)	0.0066 (4)	−0.0023 (3)
O5	0.0217 (5)	0.0151 (4)	0.0191 (5)	0.0023 (4)	0.0013 (4)	0.0006 (4)
O6	0.0279 (5)	0.0220 (5)	0.0223 (5)	0.0004 (4)	−0.0070 (4)	−0.0007 (4)
O7	0.0189 (5)	0.0142 (4)	0.0196 (4)	−0.0009 (3)	0.0018 (3)	−0.0017 (3)
O8	0.0203 (5)	0.0185 (5)	0.0204 (5)	0.0008 (4)	−0.0033 (4)	0.0003 (4)
N1	0.0143 (5)	0.0125 (6)	0.0141 (5)	−0.0004 (4)	0.0017 (4)	0.0007 (4)
N2	0.0156 (5)	0.0123 (5)	0.0146 (5)	0.0007 (4)	0.0044 (4)	0.0004 (4)
N3	0.0164 (6)	0.0170 (5)	0.0153 (5)	0.0016 (4)	0.0025 (4)	0.0005 (4)
N4	0.0209 (6)	0.0189 (5)	0.0190 (6)	0.0047 (5)	0.0044 (5)	−0.0023 (4)
N5	0.0288 (7)	0.0187 (6)	0.0184 (6)	0.0038 (5)	0.0045 (5)	−0.0021 (4)
N6	0.0173 (6)	0.0170 (5)	0.0142 (5)	−0.0004 (4)	0.0024 (4)	−0.0006 (4)
N7	0.0262 (7)	0.0201 (6)	0.0207 (6)	0.0027 (5)	0.0024 (5)	−0.0064 (5)
N8	0.0235 (7)	0.0246 (6)	0.0206 (6)	0.0001 (5)	0.0055 (5)	−0.0076 (5)
C1	0.0131 (6)	0.0156 (6)	0.0146 (6)	0.0002 (5)	0.0012 (5)	0.0022 (5)
C2	0.0165 (6)	0.0160 (6)	0.0179 (6)	−0.0003 (5)	0.0009 (5)	0.0037 (5)
C3	0.0180 (6)	0.0114 (6)	0.0210 (6)	0.0005 (5)	−0.0009 (5)	−0.0009 (5)
C4	0.0149 (6)	0.0166 (6)	0.0161 (6)	0.0006 (5)	0.0007 (5)	−0.0021 (5)
C5	0.0119 (6)	0.0162 (6)	0.0131 (6)	−0.0003 (5)	0.0000 (4)	−0.0015 (5)
C6	0.0146 (6)	0.0182 (6)	0.0147 (6)	0.0009 (5)	0.0015 (5)	0.0012 (5)
C7	0.0129 (6)	0.0155 (6)	0.0136 (6)	−0.0012 (5)	0.0004 (5)	−0.0014 (5)
C8	0.0151 (6)	0.0167 (6)	0.0135 (5)	0.0008 (5)	0.0037 (5)	−0.0014 (4)
C9	0.0167 (6)	0.0169 (6)	0.0169 (6)	−0.0023 (5)	0.0035 (5)	−0.0033 (5)
C10	0.0204 (7)	0.0118 (6)	0.0226 (6)	−0.0015 (5)	0.0071 (5)	−0.0006 (5)
C11	0.0171 (7)	0.0161 (6)	0.0174 (6)	0.0016 (5)	0.0041 (5)	0.0015 (5)
C12	0.0142 (6)	0.0156 (6)	0.0137 (6)	0.0014 (5)	0.0036 (5)	−0.0001 (5)
C13	0.0175 (7)	0.0174 (6)	0.0168 (6)	0.0005 (5)	0.0040 (5)	0.0006 (5)
C14	0.0164 (6)	0.0164 (6)	0.0162 (6)	0.0000 (5)	0.0050 (5)	−0.0012 (5)
C15	0.0168 (7)	0.0169 (6)	0.0189 (6)	−0.0015 (5)	0.0082 (5)	0.0010 (5)
C16	0.0182 (7)	0.0201 (6)	0.0231 (7)	0.0035 (6)	0.0058 (5)	0.0006 (5)
C17	0.0174 (7)	0.0270 (8)	0.0206 (6)	0.0006 (5)	0.0021 (5)	0.0029 (5)
C18	0.0202 (7)	0.0243 (7)	0.0155 (6)	−0.0022 (5)	0.0045 (5)	−0.0007 (5)
C19	0.0183 (6)	0.0171 (6)	0.0172 (6)	−0.0034 (5)	0.0073 (5)	−0.0010 (5)
C20	0.0184 (7)	0.0165 (6)	0.0174 (6)	−0.0035 (5)	0.0071 (5)	−0.0014 (5)
C21	0.0199 (7)	0.0232 (7)	0.0150 (6)	−0.0038 (5)	0.0028 (5)	−0.0018 (5)
C22	0.0172 (7)	0.0251 (7)	0.0219 (7)	−0.0007 (6)	0.0020 (5)	0.0037 (5)
C23	0.0185 (7)	0.0214 (7)	0.0245 (7)	0.0020 (5)	0.0061 (5)	−0.0004 (5)
C24	0.0173 (7)	0.0188 (6)	0.0194 (6)	−0.0038 (5)	0.0082 (5)	−0.0016 (5)
O9	0.0590 (8)	0.0185 (5)	0.0210 (5)	0.0045 (5)	0.0017 (5)	−0.0002 (4)

Geometric parameters (Å, º) top

Zn1—O1	2.1725 (10)	N8—H8m	0.895 (15)
Zn1—O3	2.1886 (11)	C1—C2	1.3868 (18)
Zn1—O5	2.2595 (9)	C1—C6	1.5216 (19)
Zn1—O7	2.2372 (8)	C2—C3	1.390 (2)
Zn1—N1	2.0107 (11)	C2—H2	0.96
Zn1—N2	2.0001 (11)	C3—C4	1.394 (2)
O1—C6	1.2676 (16)	C3—H3	0.96
O2—C6	1.2418 (17)	C4—C5	1.3810 (18)
O3—C7	1.2671 (16)	C4—H4	0.96
O4—C7	1.2460 (16)	C5—C7	1.5256 (18)
O5—C13	1.2607 (16)	C8—C9	1.3832 (18)
O6—C13	1.2481 (15)	C8—C13	1.5163 (17)
O7—C14	1.2577 (15)	C9—C10	1.3871 (17)
O8—C14	1.2508 (14)	C9—H9	0.96
N1—C1	1.3364 (18)	C10—C11	1.3920 (17)
N1—C5	1.3383 (18)	C10—H10	0.96
N2—C8	1.3380 (15)	C11—C12	1.3855 (18)
N2—C12	1.3370 (15)	C11—H11	0.96
N3—C15	1.3604 (18)	C12—C14	1.5240 (16)
N3—C19	1.3672 (16)	C15—C16	1.3945 (17)
N3—H3n	0.854 (13)	C16—C17	1.3846 (19)
N4—C15	1.3413 (17)	C16—H16	0.96
N4—H4n	0.845 (17)	C17—C18	1.378 (2)
N4—H4m	0.838 (14)	C17—H17	0.96
N5—C19	1.3457 (18)	C18—C19	1.3912 (17)
N5—H5n	0.878 (15)	C18—H18	0.96
N5—H5m	0.872 (15)	C20—C21	1.3920 (17)
N6—C20	1.3581 (16)	C21—C22	1.381 (2)
N6—C24	1.3536 (18)	C21—H21	0.96
N6—H6n	0.884 (14)	C22—C23	1.390 (2)
N7—C20	1.3429 (18)	C22—H22	0.96
N7—H7n	0.866 (15)	C23—C24	1.3934 (17)
N7—H7m	0.850 (14)	C23—H23	0.96
N8—C24	1.3437 (17)	O9—H9o	0.83 (2)
N8—H8n	0.840 (18)	O9—H9p	0.866 (19)

O1—Zn1—O3	153.16 (4)	O1—C6—O2	126.67 (13)
O1—Zn1—O5	88.95 (4)	O1—C6—C1	115.43 (12)
O1—Zn1—O7	97.34 (4)	O2—C6—C1	117.90 (11)
O1—Zn1—N1	76.69 (4)	O3—C7—O4	127.03 (12)
O1—Zn1—N2	107.41 (4)	O3—C7—C5	115.34 (11)
O3—Zn1—O5	96.92 (4)	O4—C7—C5	117.62 (11)
O3—Zn1—O7	89.46 (3)	N2—C8—C9	121.25 (11)
O3—Zn1—N1	76.46 (4)	N2—C8—C13	114.18 (11)
O3—Zn1—N2	99.43 (4)	C9—C8—C13	124.49 (10)
O5—Zn1—O7	152.52 (3)	C8—C9—C10	118.50 (11)
O5—Zn1—N1	102.81 (4)	C8—C9—H9	120.7524
O5—Zn1—N2	76.41 (4)	C10—C9—H9	120.7525
O7—Zn1—N1	104.67 (3)	C9—C10—C11	119.81 (12)
O7—Zn1—N2	76.18 (3)	C9—C10—H10	120.0969
N1—Zn1—N2	175.74 (5)	C11—C10—H10	120.0967
Zn1—O1—C6	114.92 (9)	C10—C11—C12	118.43 (11)
Zn1—O3—C7	114.97 (9)	C10—C11—H11	120.7863
Zn1—O5—C13	111.69 (7)	C12—C11—H11	120.7859
Zn1—O7—C14	112.33 (7)	N2—C12—C11	121.11 (10)
Zn1—N1—C1	119.10 (9)	N2—C12—C14	113.48 (11)
Zn1—N1—C5	119.51 (9)	C11—C12—C14	125.41 (10)
C1—N1—C5	121.36 (11)	O5—C13—O6	127.57 (11)
Zn1—N2—C8	119.46 (8)	O5—C13—C8	116.49 (10)
Zn1—N2—C12	119.26 (8)	O6—C13—C8	115.91 (11)
C8—N2—C12	120.83 (11)	O7—C14—O8	126.50 (11)
C15—N3—C19	123.53 (10)	O7—C14—C12	116.50 (10)
C15—N3—H3n	119.1 (11)	O8—C14—C12	116.99 (11)
C19—N3—H3n	117.4 (11)	N3—C15—N4	117.86 (11)
C15—N4—H4n	118.0 (10)	N3—C15—C16	118.72 (12)
C15—N4—H4m	121.9 (12)	N4—C15—C16	123.41 (13)
H4n—N4—H4m	120.0 (16)	C15—C16—C17	118.47 (13)
C19—N5—H5n	113.8 (11)	C15—C16—H16	120.7643
C19—N5—H5m	118.9 (12)	C17—C16—H16	120.7632
H5n—N5—H5m	121.5 (15)	C16—C17—C18	121.93 (12)
C20—N6—C24	124.03 (10)	C16—C17—H17	119.0364
C20—N6—H6n	116.7 (10)	C18—C17—H17	119.0372
C24—N6—H6n	119.3 (10)	C17—C18—C19	119.09 (12)
C20—N7—H7n	119.2 (11)	C17—C18—H18	120.4552
C20—N7—H7m	119.1 (12)	C19—C18—H18	120.4557
H7n—N7—H7m	121.5 (16)	N3—C19—N5	117.91 (10)
C24—N8—H8n	119.2 (10)	N3—C19—C18	118.26 (12)
C24—N8—H8m	116.3 (11)	N5—C19—C18	123.81 (12)
H8n—N8—H8m	122.5 (16)	N6—C20—N7	116.75 (11)
N1—C1—C2	120.95 (12)	N6—C20—C21	118.49 (12)
N1—C1—C6	113.37 (11)	N7—C20—C21	124.76 (12)
C2—C1—C6	125.67 (12)	C20—C21—C22	118.59 (12)
C1—C2—C3	118.25 (13)	C20—C21—H21	120.7048
C1—C2—H2	120.8742	C22—C21—H21	120.7055
C3—C2—H2	120.873	C21—C22—C23	121.98 (12)
C2—C3—C4	120.10 (12)	C21—C22—H22	119.0091
C2—C3—H3	119.9475	C23—C22—H22	119.0085
C4—C3—H3	119.949	C22—C23—C24	118.24 (13)
C3—C4—C5	118.32 (13)	C22—C23—H23	120.8827
C3—C4—H4	120.8394	C24—C23—H23	120.881
C5—C4—H4	120.8387	N6—C24—N8	116.41 (11)
N1—C5—C4	121.00 (12)	N6—C24—C23	118.68 (12)
N1—C5—C7	113.41 (11)	N8—C24—C23	124.90 (13)
C4—C5—C7	125.55 (12)	H9o—O9—H9p	104.4 (19)

O3—Zn1—O1—C6	−6.33 (14)	Zn1—N1—C1—C2	178.80 (9)
O5—Zn1—O1—C6	97.02 (9)	Zn1—N1—C1—C6	−2.24 (14)
O7—Zn1—O1—C6	−109.82 (9)	C5—N1—C1—C2	0.87 (19)
N1—Zn1—O1—C6	−6.41 (9)	C5—N1—C1—C6	179.83 (11)
N2—Zn1—O1—C6	172.42 (9)	Zn1—N1—C5—C4	−178.36 (9)
O1—Zn1—O3—C7	−4.88 (14)	Zn1—N1—C5—C7	−0.20 (14)
O5—Zn1—O3—C7	−106.37 (9)	C1—N1—C5—C4	−0.43 (19)
O7—Zn1—O3—C7	100.44 (9)	C1—N1—C5—C7	177.72 (11)
N1—Zn1—O3—C7	−4.80 (9)	Zn1—N2—C8—C9	−172.85 (10)
N2—Zn1—O3—C7	176.33 (9)	Zn1—N2—C8—C13	4.06 (14)
O1—Zn1—O5—C13	98.37 (9)	C12—N2—C8—C9	−0.59 (19)
O3—Zn1—O5—C13	−107.90 (9)	C12—N2—C8—C13	176.32 (11)
O7—Zn1—O5—C13	−5.62 (13)	Zn1—N2—C12—C11	170.43 (10)
N1—Zn1—O5—C13	174.47 (9)	Zn1—N2—C12—C14	−9.58 (14)
N2—Zn1—O5—C13	−9.83 (9)	C8—N2—C12—C11	−1.85 (19)
O1—Zn1—O7—C14	−119.53 (9)	C8—N2—C12—C14	178.14 (11)
O3—Zn1—O7—C14	86.52 (9)	N1—C1—C2—C3	−0.37 (19)
O5—Zn1—O7—C14	−17.54 (13)	C6—C1—C2—C3	−179.19 (12)
N1—Zn1—O7—C14	162.37 (9)	N1—C1—C6—O1	−3.56 (16)
N2—Zn1—O7—C14	−13.33 (8)	N1—C1—C6—O2	176.76 (11)
O1—Zn1—N1—C1	4.42 (9)	C2—C1—C6—O1	175.34 (12)
O1—Zn1—N1—C5	−177.61 (10)	C2—C1—C6—O2	−4.34 (19)
O3—Zn1—N1—C1	−175.54 (10)	C1—C2—C3—C4	−0.54 (19)
O3—Zn1—N1—C5	2.43 (9)	C2—C3—C4—C5	0.96 (19)
O5—Zn1—N1—C1	−81.39 (10)	C3—C4—C5—N1	−0.48 (19)
O5—Zn1—N1—C5	96.58 (10)	C3—C4—C5—C7	−178.40 (12)
O7—Zn1—N1—C1	98.66 (10)	N1—C5—C7—O3	−4.10 (16)
O7—Zn1—N1—C5	−83.38 (10)	N1—C5—C7—O4	177.08 (11)
O1—Zn1—N2—C8	−82.06 (10)	C4—C5—C7—O3	173.95 (12)
O1—Zn1—N2—C12	105.56 (10)	C4—C5—C7—O4	−4.86 (19)
O3—Zn1—N2—C8	97.37 (10)	N2—C8—C9—C10	2.52 (19)
O3—Zn1—N2—C12	−75.02 (10)	C13—C8—C9—C10	−174.06 (12)
O5—Zn1—N2—C8	2.46 (9)	N2—C8—C13—O5	−13.36 (17)
O5—Zn1—N2—C12	−169.93 (10)	N2—C8—C13—O6	168.57 (12)
O7—Zn1—N2—C8	−175.54 (10)	C9—C8—C13—O5	163.43 (13)
O7—Zn1—N2—C12	12.07 (9)	C9—C8—C13—O6	−14.64 (19)
Zn1—O1—C6—O2	−173.25 (11)	C8—C9—C10—C11	−2.1 (2)
Zn1—O1—C6—C1	7.10 (14)	C9—C10—C11—C12	−0.2 (2)
Zn1—O3—C7—O4	−175.28 (11)	C10—C11—C12—N2	2.2 (2)
Zn1—O3—C7—C5	6.04 (14)	C10—C11—C12—C14	−177.76 (12)
Zn1—O5—C13—O6	−167.46 (12)	N2—C12—C14—O7	−3.18 (17)
Zn1—O5—C13—C8	14.74 (14)	N2—C12—C14—O8	177.85 (11)
Zn1—O7—C14—O8	−168.70 (11)	C11—C12—C14—O7	176.81 (13)
Zn1—O7—C14—C12	12.44 (14)	C11—C12—C14—O8	−2.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O3ⁱ	0.96	2.49	3.1769 (16)	129
C18—H18···O4	0.96	2.59	3.3556 (16)	137
C22—H22···O3ⁱⁱ	0.96	2.59	3.3789 (17)	139
N3—H3n···O8ⁱⁱ	0.854 (13)	1.948 (13)	2.7845 (13)	166.0 (16)
N4—H4n···O4ⁱⁱⁱ	0.845 (17)	2.096 (17)	2.9287 (16)	168.4 (14)
N4—H4m···O7ⁱⁱ	0.838 (14)	2.357 (14)	3.1874 (14)	171.0 (17)
N5—H5n···O4	0.878 (15)	2.206 (14)	3.0600 (14)	164.2 (15)
N5—H5m···O9^iv	0.872 (15)	2.066 (15)	2.9203 (15)	166.3 (17)
N6—H6n···O6^v	0.884 (14)	1.763 (14)	2.6381 (13)	169.9 (15)
N7—H7n···O2^vi	0.866 (15)	2.032 (15)	2.8818 (15)	166.8 (17)
N8—H8n···O2^vii	0.840 (18)	2.085 (18)	2.9206 (17)	172.4 (17)
O9—H9o···O1^v	0.83 (2)	2.06 (2)	2.8936 (14)	174 (2)
O9—H9p···O8^viii	0.866 (19)	1.928 (19)	2.7462 (14)	157.1 (18)

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

Experimental details

Crystal data
Chemical formula	(C₅H₈N₃)₂[Zn(C₇H₃NO₄)₂]·H₂O
M_r	633.9
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	8.2940 (3), 13.2368 (4), 23.8063 (7)
β (°)	104.995 (3)
V (Å³)	2524.60 (14)
Z	4
Radiation type	Cu Kα
µ (mm⁻¹)	1.99
Crystal size (mm)	0.26 × 0.19 × 0.10

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with an Atlas (Gemini ultra Cu) detector
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.142, 1
No. of measured, independent and observed [I > 3σ(I)] reflections	66673, 4502, 4175
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.597

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.077, 1.61
No. of reflections	4502
No. of parameters	415
No. of restraints	12
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.32

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SIR2002 (Burla et al., 2003), JANA2006 (Petříček et al., 2007), DIAMOND (Brandenburg & Putz, 2005).

Selected bond lengths (Å) top

Zn1—O1	2.1725 (10)	Zn1—O7	2.2372 (8)
Zn1—O3	2.1886 (11)	Zn1—N1	2.0107 (11)
Zn1—O5	2.2595 (9)	Zn1—N2	2.0001 (11)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C10—H10···O3ⁱ	0.96	2.49	3.1769 (16)	129
C18—H18···O4	0.96	2.59	3.3556 (16)	137
C22—H22···O3ⁱⁱ	0.96	2.59	3.3789 (17)	139
N3—H3n···O8ⁱⁱ	0.854 (13)	1.948 (13)	2.7845 (13)	166.0 (16)
N4—H4n···O4ⁱⁱⁱ	0.845 (17)	2.096 (17)	2.9287 (16)	168.4 (14)
N4—H4m···O7ⁱⁱ	0.838 (14)	2.357 (14)	3.1874 (14)	171.0 (17)
N5—H5n···O4	0.878 (15)	2.206 (14)	3.0600 (14)	164.2 (15)
N5—H5m···O9^iv	0.872 (15)	2.066 (15)	2.9203 (15)	166.3 (17)
N6—H6n···O6^v	0.884 (14)	1.763 (14)	2.6381 (13)	169.9 (15)
N7—H7n···O2^vi	0.866 (15)	2.032 (15)	2.8818 (15)	166.8 (17)
N8—H8n···O2^vii	0.840 (18)	2.085 (18)	2.9206 (17)	172.4 (17)
O9—H9o···O1^v	0.83 (2)	2.06 (2)	2.8936 (14)	174 (2)
O9—H9p···O8^viii	0.866 (19)	1.928 (19)	2.7462 (14)	157.1 (18)

Acknowledgements

This research was supported by the Islamic Azad University, Yazd Branch (grant title: Synthesis and characterization of new complexes of zinc, nickel and cadmium with polynitrogen-containing ligands) and the project Praemium Academiae of the Academy of Sciences of the Czech Republic.

References

Brandenburg, K. & Putz, H. (2005). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Burla, M. C., Camalli, M., Carrozzini, B., Cascarano, G. L., Giacovazzo, C., Polidori, G. & Spagna, R. (2003). J. Appl. Cryst. 36, 1103. CrossRef IUCr Journals Google Scholar
Moghimi, A., Ranjbar, M., Aghabozorg, H., Jalali, F., Shamsipur, M. & Chadha, K. K. (2002a). J. Chem. Res. pp. 477–479. CrossRef Google Scholar
Moghimi, A., Ranjbar, M., Aghabozorg, H., Jalali, F., Shamsipur, M. & Chadha, K. K. (2002b). Can. J. Chem. 80, 1687–1696. CrossRef CAS Google Scholar
Moghimi, A., Sharif, M. A., Shokrollahic, A., Shamsipurc, M. & Aghabozorg, H. (2005). Z. Anorg. Allg. Chem. 631, 902–908. Web of Science CSD CrossRef CAS Google Scholar
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Oxfordshire, England. Google Scholar
Petříček, V., Dušek, M. & Palatinus, L. (2007). JANA2006. Institute of Physics, Praha, Czech Republic. Google Scholar
Ranjbar, M., Moghimi, A., Aghabozorg, H. & Yap, G. P. A. (2002). Anal. Sci. (Jpn), 18, 219–220. CrossRef CAS Google Scholar
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Volume 67| Part 6| June 2011| Pages m769-m770

doi:10.1107/S1600536811018204

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

Bis(2,6-di­amino­pyridinium) bis­­(pyridine-2,6-di­carboxyl­ato)zincate(II) monohydrate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

metal-organic compounds

Bis(2,6-diaminopyridinium) bis(pyridine-2,6-dicarboxylato)zincate(II) monohydrate