2,6-Diamino­pyridinium bis­(4-hydroxy­pyridine-2,6-dicarboxyl­ato-κ3O2,N,O6)chromate(III) dihydrate

Aghabozorg, H.; Roshan, L.; Firoozi, N.; Ghadermazi, M.; Bagheri, S.

doi:10.1107/S1600536808027347

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 9| September 2008| Pages m1208-m1209

doi:10.1107/S1600536808027347

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2,6-Diaminopyridinium bis(4-hydroxypyridine-2,6-dicarboxylato-κ³O²,N,O⁶)chromate(III) dihydrate

Hossein Aghabozorg,^a ^* Leila Roshan,^a Najmeh Firoozi,^a Mohammad Ghadermazi ^b and Sara Bagheri ^c

^aFaculty of Chemistry, Tarbiat Moallem University, 49 Mofateh Avenue 15614, Tehran, Iran, ^bDepartment of Chemistry, Faculty of Science, University of Kurdistan, Sanandaj, Iran, and ^cFaculty of Chemistry, Islamic Azad University, North Tehran Branch, Tehran, Iran
^*Correspondence e-mail: haghabozorg@yahoo.com

(Received 6 August 2008; accepted 25 August 2008; online 30 August 2008)

The reaction of chromium(III) nitrate hexahydrate, pyridine-2,6-diamine and 4-hydroxypyridine-2,6-dicarboxylic acid in a 1:2:2 molar ratio in aqueous solution resulted in the formation of the title compound, (C₅H₈N₃)[Cr(C₇H₃NO₅)₂]·2H₂O or (pydaH)[Cr(hypydc)₂]·2H₂O (where pyda is pyridine-2,6-diamine and hypydcH₂ is 4-hydroxypyridine-2,6-dicarboxylic acid). Each Cr^IIIatom is hexacoordinated by four O and two N atoms from two (hypydc)²⁻ fragments, which act as tridentate ligands, in a distorted octahedral geometry. The O—Cr—O—C torsion angles between the two planes of the (hypydc)²⁻ fragments [−99.81 (17) and 97.77 (17)°] indicate that these two units are almost perpendicular to one another. In the crystal structure, extensive O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds with D⋯A distances ranging from 2.560 (2) to 3.279 (3) Å, ion pairing, C—O⋯π [O⋯π = 3.166 (2) Å] and π–π stacking interactions between (hypydc)²⁻ and (pydaH)⁺ rings [with a centroid–centroid distance of 3.3353 (14) Å] contribute to the formation of a three-dimensional supramolecular structure.

Related literature

For related literature, see: Aghabozorg et al., (2007 ); Aghabozorg, Manteghi et al. (2008 ); Aghabozorg, Saadaty et al. (2008 ); Ranjbar et al. (2001 ); Soleimannejad et al. (2008 ).

Experimental

Crystal data

(C₅H₈N₃)[Cr(C₇H₃NO₅)₂]·2H₂O
M_r = 560.38
Monoclinic, P 2₁ /n
a = 6.9590 (4) Å
b = 20.9904 (12) Å
c = 14.8951 (8) Å
β = 95.3030 (13)°
V = 2166.4 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.61 mm⁻¹
T = 100 (2) K
0.32 × 0.08 × 0.07 mm

Data collection

Bruker APEXII CCD area-detector' diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.829, T_max = 0.959
24511 measured reflections
5229 independent reflections
3694 reflections with I > 2σ(I)
R_int = 0.078

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.104
S = 1.02
5229 reflections
336 parameters
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.57 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3NA⋯O2ⁱ	0.87	2.03	2.840 (3)	154
N4—H4NB⋯O11ⁱ	0.87	2.09	2.958 (3)	173
N4—H4NA⋯O3ⁱⁱ	0.87	2.33	3.122 (3)	151
N5—H5NB⋯O8	0.87	1.99	2.831 (3)	162
N5—H5NA⋯O2ⁱ	0.87	2.01	2.812 (3)	152
O5—H5O⋯O12	0.80	1.77	2.560 (2)	169
O10—H10O⋯O11ⁱⁱⁱ	0.80	1.83	2.624 (3)	173
O11—H11C⋯O1	0.82	1.92	2.719 (2)	163
O11—H11D⋯O7^iv	0.82	1.90	2.709 (3)	169
O12—H12A⋯O9^v	0.82	2.01	2.809 (3)	165
O12—H12B⋯O4ⁱⁱ	0.82	2.05	2.872 (3)	177
C16—H16A⋯O3ⁱⁱ	0.95	2.49	3.265 (3)	139
C18—H18A⋯O12^vi	0.95	2.59	3.279 (3)	130
Symmetry codes: (i) -x, -y+2, -z; (ii) $[x-{\script{1\over 2}}, -y+{\script{5\over 2}}, z-{\script{1\over 2}}]$ ; (iii) -x+1, -y+2, -z+1; (iv) x-1, y, z; (v) $[x+{\script{1\over 2}}, -y+{\script{5\over 2}}, z-{\script{1\over 2}}]$ ; (vi) $[x-{\script{1\over 2}}, -y+{\script{5\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; 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/S1600536808027347/ym2072sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808027347/ym2072Isup2.hkl

checkCIF report

Comment top

The molecular structure of the title compound is shown in Fig. 1. Hydrogen bond geometries are given in Table 1. According to the crystal structure, the title compound is composed of an anionic complex, [Cr(hypydc)₂]^-, protonated diamino-2,6-pyridinium as a counter ion, (pydaH)⁺, and two uncoordinated water molecules. This compound crystallizes in the monoclinic system, space group P2₁/n with four molecules in the unit cell.

The Cr^III atom is six-coordinated by two 4-hydroxypyridine-2,6-dicarboxylate, (hypydc)^2-, groups which act as tridentate ligand through one pyridine N atom and two carboxylate O atoms. N1 and N2 atoms of two (hypydc)^2- fragments occupy the axial position, while O1, O3, O6 and O8 atoms form the equatorial plane. The N1—Cr1—N2 angle [177.33 (9)°] deviates slightly from linearity. Therefore, the coordination geometry around Cr^IIIcan be described as distorted octahedral. The bond angles O6—Cr1—O1, O3—Cr1—O6, O3—Cr1—O8 and O1—Cr1—O8 (93.28 (7)°, 93.82 (7)°, 90.88 (7)° and 91.46 (7)°, respectively), and the O1—Cr1—O6—C13 and O8—Cr1—O1—C6 torsion angles (-99.81 (17)° and (97.77 (17)°, respectively) show that these two (hypydc)^2- groups are almost perpendicular. Furthermore, the bond angles O1—Cr1—O3 [156.06 (7)°] and O6—Cr1—O8 [156.99 (7)°] indicate that four carboxylate groups of the two dianions are in a flattened tetrahedral arrangement around the Cr^III atom.

In the crystal structure of (pydaH)[Cr(hypydc)₂].2H₂O, the spaces between to layers of [Cr(hypydc)₂]^- anions are filled with (pydaH)⁺cations and water molecules. There are also π-π stacking interactions between the aromatic ring of the coordinated (hypydc)^2–anion and the aromatic ring of the (pydaH)⁺ cation with distances of 3.3353 (14) Å for Cg1···Cg2. There are also C—O···π stacking interactions between C6–O2 and Cg1 with O···π distance of 3.166 (2) Å (1 - x, 2 - y, -z) [Cg1 and Cg2 are the centroid for (N1/C1—C5) and (N3/C15—C19) rings, respectively] (Fig. 2).

Intermolecular O—H···O, N—H···O and C—H···O hydrogen bonding with D···A ranging from 2.560 (2) to 3.279 (3) Å, ionpairing, π–π and C—O···π stacking interactions seem to be effective in the stabilization of the crystal structure, resulting in the formation of an interesting supramolecular structure (Fig. 3).

Related literature top

For related literature, see: Aghabozorg, Ghadermazi et al., (2007); Aghabozorg, Manteghi et al. (2008); Aghabozorg, Saadaty et al. (2008); Ranjbar et al. (2001); Soleimannejad et al. (2008).

Experimental top

An aqueous solution of CrCl₃(24 mg, 0.15 mmol), pyridine-2,6-diamine (32 mg, 0.3 mmol) and 4-Hydroxypyridine-2,6-dicarboxylic acid (54 mg, 0.3 mmol) was added to each other in a 1:2:2 molar ratio, and the reaction mixture was heated at about 50°C for 4 h. Violet crystals of the title compound were obtained from the solution after two weeks at room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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. Molecular structure of (pydaH)[Cr(hypydc)₂].2H₂O, hydrogen bonds are shown as dashed lines and thermal ellipsoids are at 50% probability level.
	Fig. 2. The π–πand C—O···π stacking interactions with the distances.
	Fig. 3. Crystal packing of the title compound showing the three dimensional H-bonded framework.

2,6-Diaminopyridinium bis(4-hydroxypyridine-2,6-dicarboxylato- κ³O²,N,O⁶)chromate(III) dihydrate top

Crystal data top

(C₅H₈N₃)[Cr(C₇H₃NO₅)₂]·2H₂O	F(000) = 1148
M_r = 560.38	D_x = 1.718 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 1320 reflections
a = 6.9590 (4) Å	θ = 3–28°
b = 20.9904 (12) Å	µ = 0.61 mm⁻¹
c = 14.8951 (8) Å	T = 100 K
β = 95.3030 (13)°	Needle, black
V = 2166.4 (2) Å³	0.32 × 0.08 × 0.07 mm
Z = 4

Data collection top

Bruker APEXII CCD area-detector' diffractometer	5229 independent reflections
Radiation source: fine-focus sealed tube	3694 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.078
ω scans	θ_max = 28.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→9
T_min = 0.829, T_max = 0.959	k = −27→27
24511 measured reflections	l = −19→19

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)] = 0.042	Hydrogen site location: mixed
wR(F²) = 0.104	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0468P)² + 0.9675P] where P = (F_o² + 2F_c²)/3
5229 reflections	(Δ/σ)_max = 0.002
336 parameters	Δρ_max = 0.47 e Å⁻³
0 restraints	Δρ_min = −0.57 e Å⁻³

Crystal data top

(C₅H₈N₃)[Cr(C₇H₃NO₅)₂]·2H₂O	V = 2166.4 (2) Å³
M_r = 560.38	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.9590 (4) Å	µ = 0.61 mm⁻¹
b = 20.9904 (12) Å	T = 100 K
c = 14.8951 (8) Å	0.32 × 0.08 × 0.07 mm
β = 95.3030 (13)°

Data collection top

Bruker APEXII CCD area-detector' diffractometer	5229 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	3694 reflections with I > 2σ(I)
T_min = 0.829, T_max = 0.959	R_int = 0.078
24511 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.104	H-atom parameters constrained
S = 1.02	Δρ_max = 0.47 e Å⁻³
5229 reflections	Δρ_min = −0.57 e Å⁻³
336 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
Cr1	0.46263 (6)	1.098248 (19)	0.20578 (3)	0.00992 (10)
O1	0.3226 (2)	1.01686 (8)	0.17083 (11)	0.0124 (4)
O2	0.1871 (3)	0.95887 (8)	0.05618 (11)	0.0141 (4)
O3	0.5836 (2)	1.18207 (8)	0.18501 (11)	0.0127 (4)
O4	0.6584 (3)	1.25241 (8)	0.08081 (12)	0.0154 (4)
O5	0.3766 (3)	1.11140 (8)	−0.20081 (11)	0.0166 (4)
H5O	0.4037	1.1423	−0.2284	0.020*
O6	0.7149 (2)	1.05418 (8)	0.23449 (11)	0.0138 (4)
O7	0.9177 (3)	1.01550 (9)	0.34882 (12)	0.0192 (4)
O8	0.2157 (2)	1.14101 (8)	0.23077 (11)	0.0135 (4)
O9	0.0389 (3)	1.17639 (9)	0.33928 (12)	0.0174 (4)
O10	0.5003 (3)	1.09070 (9)	0.61131 (11)	0.0190 (4)
H10O	0.6029	1.0846	0.6388	0.023*
O11	0.1788 (3)	0.93417 (8)	0.28815 (12)	0.0159 (4)
H11D	0.0901	0.9544	0.3071	0.019*
H11C	0.2300	0.9525	0.2480	0.046 (11)*
O12	0.4442 (3)	1.21870 (8)	−0.27326 (12)	0.0170 (4)
H12A	0.4497	1.2508	−0.2418	0.020*
H12B	0.3656	1.2273	−0.3160	0.020*
N1	0.4410 (3)	1.10250 (10)	0.07265 (13)	0.0106 (4)
N2	0.4719 (3)	1.09238 (9)	0.33828 (13)	0.0105 (4)
N3	−0.0320 (3)	1.16527 (10)	−0.07279 (13)	0.0117 (4)
H3NA	−0.0906	1.1294	−0.0859	0.014*
N4	−0.0433 (3)	1.19284 (11)	−0.22368 (14)	0.0178 (5)
H4NB	−0.0924	1.1563	−0.2413	0.021*
H4NA	−0.0025	1.2175	−0.2648	0.032 (9)*
N5	−0.0454 (3)	1.13054 (10)	0.07407 (14)	0.0135 (4)
H5NB	0.0119	1.1350	0.1281	0.016*
H5NA	−0.0986	1.0961	0.0506	0.016*
C1	0.3476 (3)	1.05598 (11)	0.02427 (16)	0.0101 (5)
C2	0.3233 (4)	1.05809 (12)	−0.06822 (16)	0.0117 (5)
H2A	0.2573	1.0250	−0.1019	0.014*
C3	0.3993 (3)	1.11092 (11)	−0.11176 (16)	0.0108 (5)
C4	0.4932 (3)	1.15980 (12)	−0.05965 (16)	0.0110 (5)
H4A	0.5443	1.1959	−0.0876	0.013*
C5	0.5088 (3)	1.15376 (11)	0.03232 (16)	0.0108 (5)
C6	0.2781 (3)	1.00555 (11)	0.08605 (16)	0.0105 (5)
C7	0.5931 (3)	1.20100 (12)	0.10225 (16)	0.0111 (5)
C8	0.6272 (4)	1.06604 (12)	0.38294 (16)	0.0123 (5)
C9	0.6455 (4)	1.06333 (12)	0.47589 (16)	0.0122 (5)
H9A	0.7555	1.0444	0.5078	0.015*
C10	0.4959 (4)	1.08960 (11)	0.52222 (16)	0.0137 (5)
C11	0.3335 (4)	1.11654 (12)	0.47336 (17)	0.0137 (5)
H11A	0.2305	1.1339	0.5032	0.016*
C12	0.3287 (4)	1.11698 (11)	0.38087 (16)	0.0117 (5)
C13	0.7689 (4)	1.04231 (12)	0.31917 (16)	0.0128 (5)
C14	0.1782 (4)	1.14746 (11)	0.31450 (16)	0.0118 (5)
C15	0.0192 (4)	1.20629 (12)	−0.13776 (17)	0.0132 (5)
C16	0.1308 (4)	1.25899 (12)	−0.11129 (17)	0.0149 (5)
H16A	0.1713	1.2879	−0.1549	0.018*
C17	0.1819 (4)	1.26871 (12)	−0.02048 (17)	0.0138 (5)
H17A	0.2600	1.3044	−0.0023	0.017*
C18	0.1230 (4)	1.22815 (12)	0.04490 (17)	0.0135 (5)
H18A	0.1551	1.2368	0.1071	0.016*
C19	0.0162 (4)	1.17463 (12)	0.01759 (16)	0.0122 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cr1	0.0125 (2)	0.0104 (2)	0.00680 (19)	0.00029 (16)	0.00056 (14)	−0.00067 (15)
O1	0.0170 (9)	0.0115 (9)	0.0083 (9)	−0.0017 (7)	0.0000 (7)	0.0004 (6)
O2	0.0167 (9)	0.0123 (9)	0.0131 (9)	−0.0027 (7)	0.0006 (7)	−0.0010 (7)
O3	0.0161 (9)	0.0135 (9)	0.0084 (9)	−0.0023 (7)	0.0003 (7)	−0.0013 (7)
O4	0.0189 (10)	0.0120 (9)	0.0149 (10)	−0.0027 (8)	−0.0011 (7)	0.0010 (7)
O5	0.0284 (11)	0.0143 (10)	0.0068 (9)	−0.0023 (8)	0.0011 (7)	0.0021 (7)
O6	0.0143 (9)	0.0156 (9)	0.0114 (9)	0.0019 (7)	0.0014 (7)	−0.0015 (7)
O7	0.0170 (10)	0.0241 (11)	0.0161 (10)	0.0082 (8)	−0.0007 (7)	−0.0006 (8)
O8	0.0135 (9)	0.0175 (9)	0.0092 (9)	0.0023 (7)	−0.0002 (7)	−0.0007 (7)
O9	0.0177 (10)	0.0214 (10)	0.0134 (10)	0.0071 (8)	0.0029 (7)	−0.0001 (7)
O10	0.0214 (10)	0.0279 (11)	0.0073 (9)	0.0029 (8)	−0.0010 (7)	−0.0002 (7)
O11	0.0169 (10)	0.0181 (10)	0.0136 (9)	0.0020 (8)	0.0052 (7)	0.0022 (7)
O12	0.0230 (10)	0.0145 (9)	0.0128 (9)	−0.0013 (8)	−0.0018 (7)	0.0020 (7)
N1	0.0102 (10)	0.0101 (10)	0.0117 (10)	0.0019 (8)	0.0014 (8)	−0.0019 (8)
N2	0.0125 (10)	0.0100 (10)	0.0088 (10)	0.0002 (8)	0.0003 (8)	−0.0009 (8)
N3	0.0133 (11)	0.0102 (10)	0.0118 (11)	−0.0008 (8)	0.0018 (8)	0.0010 (8)
N4	0.0215 (12)	0.0190 (12)	0.0125 (11)	−0.0055 (10)	−0.0010 (9)	0.0041 (9)
N5	0.0147 (11)	0.0158 (11)	0.0097 (10)	−0.0018 (9)	−0.0007 (8)	−0.0002 (8)
C1	0.0092 (12)	0.0094 (12)	0.0118 (12)	0.0024 (9)	0.0024 (9)	−0.0006 (9)
C2	0.0116 (12)	0.0098 (12)	0.0132 (13)	0.0025 (9)	−0.0008 (9)	−0.0012 (9)
C3	0.0117 (12)	0.0140 (13)	0.0066 (11)	0.0042 (10)	0.0001 (9)	−0.0002 (9)
C4	0.0102 (12)	0.0115 (12)	0.0114 (12)	0.0030 (9)	0.0018 (9)	0.0018 (9)
C5	0.0081 (12)	0.0110 (12)	0.0134 (13)	0.0015 (9)	0.0017 (9)	−0.0007 (9)
C6	0.0103 (12)	0.0116 (12)	0.0099 (12)	0.0025 (10)	0.0030 (9)	0.0002 (9)
C7	0.0088 (12)	0.0133 (12)	0.0113 (12)	0.0031 (10)	0.0011 (9)	−0.0018 (9)
C8	0.0129 (13)	0.0105 (12)	0.0134 (13)	−0.0018 (10)	−0.0002 (10)	−0.0004 (9)
C9	0.0140 (13)	0.0112 (12)	0.0110 (12)	0.0022 (10)	−0.0014 (9)	0.0005 (9)
C10	0.0201 (13)	0.0110 (12)	0.0098 (12)	−0.0014 (10)	0.0008 (10)	0.0015 (9)
C11	0.0160 (13)	0.0123 (12)	0.0132 (13)	−0.0016 (10)	0.0037 (10)	−0.0013 (9)
C12	0.0122 (12)	0.0100 (12)	0.0124 (12)	−0.0020 (9)	−0.0011 (9)	−0.0021 (9)
C13	0.0154 (13)	0.0117 (12)	0.0113 (12)	−0.0009 (10)	0.0011 (10)	−0.0017 (9)
C14	0.0145 (13)	0.0109 (12)	0.0098 (12)	−0.0008 (10)	0.0005 (9)	0.0003 (9)
C15	0.0130 (13)	0.0143 (13)	0.0123 (13)	0.0050 (10)	0.0016 (10)	0.0030 (9)
C16	0.0150 (13)	0.0125 (13)	0.0173 (14)	0.0019 (10)	0.0030 (10)	0.0039 (10)
C17	0.0111 (12)	0.0088 (12)	0.0214 (14)	0.0015 (10)	0.0010 (10)	−0.0017 (10)
C18	0.0120 (13)	0.0130 (13)	0.0154 (13)	0.0014 (10)	0.0000 (10)	−0.0025 (10)
C19	0.0090 (12)	0.0152 (13)	0.0123 (13)	0.0034 (10)	−0.0001 (9)	−0.0002 (9)

Geometric parameters (Å, º) top

Cr1—N2	1.973 (2)	N4—C15	1.343 (3)
Cr1—N1	1.977 (2)	N4—H4NB	0.8700
Cr1—O3	1.9872 (17)	N4—H4NA	0.8700
Cr1—O6	1.9957 (18)	N5—C19	1.347 (3)
Cr1—O8	2.0036 (17)	N5—H5NB	0.8700
Cr1—O1	2.0111 (17)	N5—H5NA	0.8701
O1—C6	1.294 (3)	C1—C2	1.373 (3)
O2—C6	1.227 (3)	C1—C6	1.511 (3)
O3—C7	1.303 (3)	C2—C3	1.412 (3)
O4—C7	1.225 (3)	C2—H2A	0.9500
O5—C3	1.321 (3)	C3—C4	1.410 (3)
O5—H5O	0.7999	C4—C5	1.370 (3)
O6—C13	1.306 (3)	C4—H4A	0.9500
O7—C13	1.225 (3)	C5—C7	1.516 (3)
O8—C14	1.305 (3)	C8—C9	1.380 (3)
O9—C14	1.229 (3)	C8—C13	1.515 (3)
O10—C10	1.325 (3)	C9—C10	1.413 (3)
O10—H10O	0.8000	C9—H9A	0.9500
O11—H11D	0.8199	C10—C11	1.405 (4)
O11—H11C	0.8201	C11—C12	1.375 (3)
O12—H12A	0.8198	C11—H11A	0.9500
O12—H12B	0.8201	C12—C14	1.514 (3)
N1—C5	1.339 (3)	C15—C16	1.388 (4)
N1—C1	1.345 (3)	C16—C17	1.382 (4)
N2—C12	1.334 (3)	C16—H16A	0.9500
N2—C8	1.335 (3)	C17—C18	1.384 (4)
N3—C15	1.367 (3)	C17—H17A	0.9500
N3—C19	1.371 (3)	C18—C19	1.387 (3)
N3—H3NA	0.8701	C18—H18A	0.9500

N2—Cr1—N1	177.33 (9)	C5—C4—H4A	120.9
N2—Cr1—O3	103.64 (8)	C3—C4—H4A	120.9
N1—Cr1—O3	78.35 (8)	N1—C5—C4	121.6 (2)
N2—Cr1—O6	79.04 (8)	N1—C5—C7	110.3 (2)
N1—Cr1—O6	102.70 (8)	C4—C5—C7	128.0 (2)
O3—Cr1—O6	93.82 (7)	O2—C6—O1	124.7 (2)
N2—Cr1—O8	77.96 (8)	O2—C6—C1	121.4 (2)
N1—Cr1—O8	100.31 (8)	O1—C6—C1	113.9 (2)
O3—Cr1—O8	90.88 (7)	O4—C7—O3	124.6 (2)
O6—Cr1—O8	156.99 (7)	O4—C7—C5	121.8 (2)
N2—Cr1—O1	100.15 (8)	O3—C7—C5	113.6 (2)
N1—Cr1—O1	77.79 (8)	N2—C8—C9	120.8 (2)
O3—Cr1—O1	156.06 (7)	N2—C8—C13	111.6 (2)
O6—Cr1—O1	93.28 (7)	C9—C8—C13	127.6 (2)
O8—Cr1—O1	91.46 (7)	C8—C9—C10	118.0 (2)
C6—O1—Cr1	118.37 (15)	C8—C9—H9A	121.0
C7—O3—Cr1	118.46 (15)	C10—C9—H9A	121.0
C3—O5—H5O	120.7	O10—C10—C11	117.1 (2)
C13—O6—Cr1	117.65 (15)	O10—C10—C9	123.1 (2)
C14—O8—Cr1	118.36 (15)	C11—C10—C9	119.8 (2)
C10—O10—H10O	116.5	C12—C11—C10	117.7 (2)
H11D—O11—H11C	113.6	C12—C11—H11A	121.1
H12A—O12—H12B	104.7	C10—C11—H11A	121.1
C5—N1—C1	121.1 (2)	N2—C12—C11	121.6 (2)
C5—N1—Cr1	119.27 (16)	N2—C12—C14	110.8 (2)
C1—N1—Cr1	119.54 (16)	C11—C12—C14	127.5 (2)
C12—N2—C8	121.9 (2)	O7—C13—O6	126.4 (2)
C12—N2—Cr1	119.67 (17)	O7—C13—C8	120.2 (2)
C8—N2—Cr1	118.33 (16)	O6—C13—C8	113.4 (2)
C15—N3—C19	123.3 (2)	O9—C14—O8	124.9 (2)
C15—N3—H3NA	122.3	O9—C14—C12	122.0 (2)
C19—N3—H3NA	114.3	O8—C14—C12	113.1 (2)
C15—N4—H4NB	123.8	N4—C15—N3	117.4 (2)
C15—N4—H4NA	116.6	N4—C15—C16	124.2 (2)
H4NB—N4—H4NA	117.1	N3—C15—C16	118.5 (2)
C19—N5—H5NB	111.0	C17—C16—C15	118.9 (2)
C19—N5—H5NA	117.8	C17—C16—H16A	120.6
H5NB—N5—H5NA	127.1	C15—C16—H16A	120.6
N1—C1—C2	121.5 (2)	C16—C17—C18	122.1 (2)
N1—C1—C6	110.4 (2)	C16—C17—H17A	118.9
C2—C1—C6	128.1 (2)	C18—C17—H17A	118.9
C1—C2—C3	118.0 (2)	C17—C18—C19	118.5 (2)
C1—C2—H2A	121.0	C17—C18—H18A	120.7
C3—C2—H2A	121.0	C19—C18—H18A	120.7
O5—C3—C4	123.6 (2)	N5—C19—N3	116.8 (2)
O5—C3—C2	116.9 (2)	N5—C19—C18	124.5 (2)
C4—C3—C2	119.5 (2)	N3—C19—C18	118.7 (2)
C5—C4—C3	118.2 (2)

N2—Cr1—O1—C6	175.80 (17)	C3—C4—C5—C7	−176.5 (2)
N1—Cr1—O1—C6	−2.46 (16)	Cr1—O1—C6—O2	−177.36 (19)
O3—Cr1—O1—C6	2.3 (3)	Cr1—O1—C6—C1	2.3 (3)
O6—Cr1—O1—C6	−104.75 (17)	N1—C1—C6—O2	179.2 (2)
O8—Cr1—O1—C6	97.77 (17)	C2—C1—C6—O2	−0.1 (4)
N2—Cr1—O3—C7	−177.73 (16)	N1—C1—C6—O1	−0.5 (3)
N1—Cr1—O3—C7	0.44 (17)	C2—C1—C6—O1	−179.8 (2)
O6—Cr1—O3—C7	102.64 (17)	Cr1—O3—C7—O4	177.52 (19)
O8—Cr1—O3—C7	−99.91 (17)	Cr1—O3—C7—C5	−0.6 (3)
O1—Cr1—O3—C7	−4.3 (3)	N1—C5—C7—O4	−177.7 (2)
N2—Cr1—O6—C13	−0.10 (17)	C4—C5—C7—O4	0.4 (4)
N1—Cr1—O6—C13	−178.02 (17)	N1—C5—C7—O3	0.5 (3)
O3—Cr1—O6—C13	103.07 (17)	C4—C5—C7—O3	178.6 (2)
O8—Cr1—O6—C13	1.7 (3)	C12—N2—C8—C9	−0.1 (4)
O1—Cr1—O6—C13	−99.81 (17)	Cr1—N2—C8—C9	176.98 (18)
N2—Cr1—O8—C14	2.31 (17)	C12—N2—C8—C13	−179.5 (2)
N1—Cr1—O8—C14	−179.77 (17)	Cr1—N2—C8—C13	−2.4 (3)
O3—Cr1—O8—C14	−101.46 (17)	N2—C8—C9—C10	−0.4 (4)
O6—Cr1—O8—C14	0.5 (3)	C13—C8—C9—C10	178.9 (2)
O1—Cr1—O8—C14	102.37 (17)	C8—C9—C10—O10	−178.7 (2)
O3—Cr1—N1—C5	−0.11 (17)	C8—C9—C10—C11	0.9 (4)
O6—Cr1—N1—C5	−91.45 (18)	O10—C10—C11—C12	178.6 (2)
O8—Cr1—N1—C5	88.65 (18)	C9—C10—C11—C12	−1.0 (4)
O1—Cr1—N1—C5	177.91 (19)	C8—N2—C12—C11	0.0 (4)
O3—Cr1—N1—C1	−175.84 (19)	Cr1—N2—C12—C11	−176.99 (18)
O6—Cr1—N1—C1	92.83 (18)	C8—N2—C12—C14	176.2 (2)
O8—Cr1—N1—C1	−87.08 (18)	Cr1—N2—C12—C14	−0.8 (3)
O1—Cr1—N1—C1	2.18 (17)	C10—C11—C12—N2	0.5 (4)
O3—Cr1—N2—C12	87.31 (19)	C10—C11—C12—C14	−175.0 (2)
O6—Cr1—N2—C12	178.62 (19)	Cr1—O6—C13—O7	179.5 (2)
O8—Cr1—N2—C12	−0.64 (18)	Cr1—O6—C13—C8	−1.1 (3)
O1—Cr1—N2—C12	−89.97 (19)	N2—C8—C13—O7	−178.4 (2)
O3—Cr1—N2—C8	−89.81 (18)	C9—C8—C13—O7	2.3 (4)
O6—Cr1—N2—C8	1.50 (18)	N2—C8—C13—O6	2.2 (3)
O8—Cr1—N2—C8	−177.77 (19)	C9—C8—C13—O6	−177.1 (2)
O1—Cr1—N2—C8	92.91 (18)	Cr1—O8—C14—O9	174.9 (2)
C5—N1—C1—C2	2.1 (3)	Cr1—O8—C14—C12	−3.3 (3)
Cr1—N1—C1—C2	177.73 (18)	N2—C12—C14—O9	−175.7 (2)
C5—N1—C1—C6	−177.3 (2)	C11—C12—C14—O9	0.2 (4)
Cr1—N1—C1—C6	−1.6 (3)	N2—C12—C14—O8	2.6 (3)
N1—C1—C2—C3	−0.1 (3)	C11—C12—C14—O8	178.5 (2)
C6—C1—C2—C3	179.1 (2)	C19—N3—C15—N4	−177.6 (2)
C1—C2—C3—O5	179.0 (2)	C19—N3—C15—C16	2.1 (4)
C1—C2—C3—C4	−1.2 (3)	N4—C15—C16—C17	178.2 (2)
O5—C3—C4—C5	−179.6 (2)	N3—C15—C16—C17	−1.5 (4)
C2—C3—C4—C5	0.6 (3)	C15—C16—C17—C18	−1.0 (4)
C1—N1—C5—C4	−2.7 (3)	C16—C17—C18—C19	2.8 (4)
Cr1—N1—C5—C4	−178.40 (18)	C15—N3—C19—N5	179.4 (2)
C1—N1—C5—C7	175.5 (2)	C15—N3—C19—C18	−0.3 (4)
Cr1—N1—C5—C7	−0.2 (3)	C17—C18—C19—N5	178.2 (2)
C3—C4—C5—N1	1.4 (4)	C17—C18—C19—N3	−2.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3NA···O2ⁱ	0.87	2.03	2.840 (3)	154
N4—H4NB···O11ⁱ	0.87	2.09	2.958 (3)	173
N4—H4NA···O3ⁱⁱ	0.87	2.33	3.122 (3)	151
N5—H5NB···O8	0.87	1.99	2.831 (3)	162
N5—H5NA···O2ⁱ	0.87	2.01	2.812 (3)	152
O5—H5O···O12	0.80	1.77	2.560 (2)	169
O10—H10O···O11ⁱⁱⁱ	0.80	1.83	2.624 (3)	173
O11—H11C···O1	0.82	1.92	2.719 (2)	163
O11—H11D···O7^iv	0.82	1.90	2.709 (3)	169
O12—H12A···O9^v	0.82	2.01	2.809 (3)	165
O12—H12B···O4ⁱⁱ	0.82	2.05	2.872 (3)	177
C16—H16A···O3ⁱⁱ	0.95	2.49	3.265 (3)	139
C18—H18A···O12^vi	0.95	2.59	3.279 (3)	130

Symmetry codes: (i) −x, −y+2, −z; (ii) x−1/2, −y+5/2, z−1/2; (iii) −x+1, −y+2, −z+1; (iv) x−1, y, z; (v) x+1/2, −y+5/2, z−1/2; (vi) x−1/2, −y+5/2, z+1/2.

Experimental details

Crystal data
Chemical formula	(C₅H₈N₃)[Cr(C₇H₃NO₅)₂]·2H₂O
M_r	560.38
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	6.9590 (4), 20.9904 (12), 14.8951 (8)
β (°)	95.3030 (13)
V (Å³)	2166.4 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.61
Crystal size (mm)	0.32 × 0.08 × 0.07

Data collection
Diffractometer	Bruker APEXII CCD area-detector' diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.829, 0.959
No. of measured, independent and observed [I > 2σ(I)] reflections	24511, 5229, 3694
R_int	0.078
(sin θ/λ)_max (Å⁻¹)	0.661

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.104, 1.02
No. of reflections	5229
No. of parameters	336
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.57

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), 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—H3NA···O2ⁱ	0.87	2.03	2.840 (3)	154
N4—H4NB···O11ⁱ	0.87	2.09	2.958 (3)	173
N4—H4NA···O3ⁱⁱ	0.87	2.33	3.122 (3)	151
N5—H5NB···O8	0.87	1.99	2.831 (3)	162
N5—H5NA···O2ⁱ	0.87	2.01	2.812 (3)	152
O5—H5O···O12	0.80	1.77	2.560 (2)	169
O10—H10O···O11ⁱⁱⁱ	0.80	1.83	2.624 (3)	173
O11—H11C···O1	0.82	1.92	2.719 (2)	163
O11—H11D···O7^iv	0.82	1.90	2.709 (3)	169
O12—H12A···O9^v	0.82	2.01	2.809 (3)	165
O12—H12B···O4ⁱⁱ	0.82	2.05	2.872 (3)	177
C16—H16A···O3ⁱⁱ	0.95	2.49	3.265 (3)	139
C18—H18A···O12^vi	0.95	2.59	3.279 (3)	130

Symmetry codes: (i) −x, −y+2, −z; (ii) x−1/2, −y+5/2, z−1/2; (iii) −x+1, −y+2, −z+1; (iv) x−1, y, z; (v) x+1/2, −y+5/2, z−1/2; (vi) x−1/2, −y+5/2, z+1/2.

References

Aghabozorg, H., Ghadermazi, M., Soleimannejad, J. & Sheshmani, S. (2007). Acta Cryst. E63, m1917–m1918. 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., Saadaty, S., Motyeian, E., Ghadermazi, M. & Manteghi, F. (2008). Acta Cryst. E64, m466–m467. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Ranjbar, M., Aghabozorg, H., Moghimi, A. & Yanovsky, A. (2001). Z. Kristallogr. New Cryst. Struct. 216, 626–628. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Soleimannejad, J., Aghabozorg, H. & Hooshmand, S. (2008). Acta Cryst. E64, m564–m565. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 64| Part 9| September 2008| Pages m1208-m1209

doi:10.1107/S1600536808027347

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