Bis(2,4,6-triamino-1,3,5-triazin-1-ium) bis­(4-hydroxy­pyridine-2,6-carboxyl­ato)­cuprate(II) hexa­hydrate

Ramos Silva, M.; Motyeian, E.; Aghabozorg, H.; Ghadermazi, M.

doi:10.1107/S160053680802566X

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 9| September 2008| Pages m1173-m1174

doi:10.1107/S160053680802566X

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Bis(2,4,6-triamino-1,3,5-triazin-1-ium) bis(4-hydroxypyridine-2,6-carboxylato)cuprate(II) hexahydrate

Manuela Ramos Silva,^a ^* Elham Motyeian,^b Hossein Aghabozorg ^c and Mohammad Ghadermazi ^d

^aCEMDRX, Physics Department, University of Coimbra, P-3004-516 Coimbra, Portugal, ^bDepartment of Chemistry, Faculty of Science, Payame Noor University, Qom Center, Qom, Iran, ^cFaculty of Chemistry, Tarbiat Moallem University, 49 Mofateh Avenue, 15614 Tehran, Iran, and ^dDepartment of Chemistry, Faculty of Science, University of Kurdistan, Sanandaj, Iran
^*Correspondence e-mail: manuela@pollux.fis.uc.pt

(Received 5 August 2008; accepted 8 August 2008; online 16 August 2008)

In the title compound, (C₃H₇N₆)₂[Cu(C₇H₃NO₅)₂]·6H₂O, the coordination geometry of the Cu^II atom can be described as distorted octahedral. The equatorial plane is defined by four O atoms from two 4-hydroxypyridine-2,6-dicarboxylate ligands. The axial positions are occupied by the N atoms of the same ligands. There is an extensive three-dimensional hydrogen-bond network reinforcing crystal cohesion.

Related literature

For related literature, see: Aghabozorg, Motyeian, Attar Gharamaleki et al. (2008 ); Aghabozorg, Motyeian, Soleimannejad et al. (2008 ); Aghabozorg, Saadaty et al. (2008 ).

Experimental

Crystal data

(C₃H₇N₆)₂[Cu(C₇H₃NO₅)₂]·6H₂O
M_r = 788.14
Monoclinic, P 2₁ /c
a = 11.2894 (3) Å
b = 37.7699 (12) Å
c = 7.3414 (2) Å
β = 94.016 (2)°
V = 3122.68 (15) Å³
Z = 4
Mo Kα radiation
μ = 0.80 mm⁻¹
T = 293 (2) K
0.28 × 0.20 × 0.10 mm

Data collection

Bruker APEX CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2000 ) T_min = 0.714, T_max = 0.919
22082 measured reflections
7390 independent reflections
5112 reflections with I > 2σ(I)
R_int = 0.054

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.116
S = 1.02
7390 reflections
508 parameters
13 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1A—H1A⋯O7ⁱ	0.74 (3)	1.84 (3)	2.573 (3)	169 (4)
O1B—H1B⋯O6ⁱⁱ	0.76 (4)	1.83 (4)	2.579 (3)	173 (4)
N5A—H5A⋯O10ⁱⁱ	0.77 (2)	2.06 (3)	2.787 (3)	159 (3)
N6A—H7⋯O4Bⁱⁱⁱ	0.86	2.13	2.980 (3)	173
N6A—H8⋯O11	0.86	2.13	2.962 (4)	162
N7A—H11⋯O1Bⁱⁱⁱ	0.86	2.25	3.106 (3)	172
N7A—H12⋯O9^iv	0.86	2.11	2.910 (4)	155
N8A—H9⋯N3A^v	0.86	2.11	2.973 (4)	177
N8A—H10⋯O10ⁱⁱ	0.86	2.25	2.986 (4)	144
N8A—H10⋯O11^v	0.86	2.56	3.202 (4)	133
N5B—H5B⋯O2A^vi	0.78 (2)	1.96 (3)	2.698 (3)	157 (3)
N6B—H5⋯O1Aⁱ	0.86	2.28	3.131 (3)	170
N6B—H6⋯O9	0.86	2.38	2.905 (3)	120
N7B—H1⋯O5B^vii	0.86	2.24	3.021 (3)	151
N7B—H2⋯O2A^vi	0.86	2.11	2.852 (3)	144
N8B—H3⋯O4Aⁱ	0.86	2.10	2.930 (3)	163
N8B—H4⋯O8^vi	0.86	2.01	2.857 (3)	169
O6—H61⋯O5A	0.83 (2)	1.87 (2)	2.706 (3)	177 (4)
O6—H62⋯O2B^viii	0.81 (2)	1.97 (2)	2.756 (3)	163 (4)
O7—H71⋯O3B^viii	0.82 (2)	1.94 (2)	2.741 (3)	163 (4)
O7—H72⋯O5B	0.82 (2)	1.95 (2)	2.766 (3)	171 (4)
O8—H81⋯O4Bⁱⁱⁱ	0.86 (2)	1.86 (2)	2.714 (3)	173 (4)
O8—H82⋯O3A	0.83 (2)	1.90 (2)	2.701 (3)	162 (4)
O9—H91⋯O3B	0.88 (2)	1.97 (2)	2.839 (3)	172 (4)
O9—H92⋯O4Aⁱⁱⁱ	0.88 (2)	2.13 (2)	3.005 (3)	176 (4)
O10—H101⋯O8^ix	0.84 (4)	2.24 (3)	3.030 (4)	157 (5)
O10—H102⋯O4A	0.89 (4)	2.39 (5)	2.695 (3)	101 (4)
O11—H111⋯O10^x	0.85 (2)	2.44 (4)	3.196 (5)	149 (7)
O11—H112⋯N4B^x	0.83 (6)	2.53 (7)	2.996 (4)	116 (6)
O11—H112⋯O8	0.83 (6)	2.60 (8)	3.090 (5)	118 (7)
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+1, -y+2, -z+1; (iii) x, y, z-1; (iv) -x+1, -y+2, -z; (v) -x, -y+2, -z+1; (vi) $[x+1, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (vii) x+1, y, z; (viii) x, y, z+1; (ix) x+1, y, z+1; (x) x-1, y, z.

Data collection: SMART (Bruker, 2003 ); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680802566X/bt2763sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680802566X/bt2763Isup2.hkl

checkCIF report

Comment top

Following our research on the synthesis of proton transfer compounds that can function as suitable ligands in the synthesis of metal complexes (Aghabozorg, Motyeian, Attar Gharamaleki et al., 2008; Aghabozorg, Motyeian, Soleimannejad et al., 2008; Aghabozorg, Saadaty et al., 2008), we have obtained the title compound dimelaminium bis(4-hydroxypyridine-2,6-carboxylato)cuprate(II) hexahydrated. 4-hydroxypyridine-2,6-carboxylic acid (hypydcH2) was chosen as a proton donor and melamine (tata) as the proton acceptor.

The asymmetric unit of (I) consists of two melaminium (tataH) residues protonated at one ring N atom, two (hypydc) residues coordinating a Cu^II ion and six water molecules (Fig. 1). The melaminium cations are essentially planar with the weighted average absolute torsion angle equal to 0.67 (23) for ring A and 1.20 (33)° for ring B. Both rings exhibit a significant distortion from the ideal hexagonal form. The internal C—N—C angle of the protonated N atom (N5A, N5B) is significantly larger than the other two ring C—N—C angles (Table 1). The angle between the least-squares plane of the two independent cations is 87.97 (12)°. The anions also assemble perpendicularly to each other. The angle between the mean planes of the two independent pyridil rings is 89.51 (12)°. Thus the molecules form a square grid with channels along the b axis (Fig. 2). The Cu^II ion is coordinated octahedrally by two ligands of (hypydc). The N atoms of the two independent anions occupy the axial positions while four oxygen atoms form the equatorial plane. There is an extensive network of hydrogen bonds proportionated by the large amount of water molecules. All the water molecules share their hydrogen atoms with another strong acceptor (N,O). The (hypydc) anions have similar H-bonds, but the two independent melaminium cations have different roles in the web of H-bonds. While B molecules only establish H-bonds to neighbouring water or (hypydc) molecules, the A molecules are also joined in dimers (Fig.3, Table 2).

Related literature top

For related literature, see: Aghabozorg, Motyeian, Attar Gharamaleki et al. (2008); Aghabozorg, Motyeian, Soleimannejad et al. (2008); Aghabozorg, Saadaty et al. (2008).

Experimental top

The proton transfer compound, (tata)₂(hypydc), was prepared by the reaction of 4-hydroxypyridinee-2,6-dicarboxylic acid, hypydcH₂, with melamine, (tata). The reaction between Cu(NO₃)₂.6H₂O (143 mg, 0.5 mmol) in water (20 ml) and proton transfer compound, (phenH)₂(hypydc) (253 mg, 1.0 mmol) in water (20 ml), in a 1:2 molar ratio was carried out and a blue crystalline compound was obtained by the slow evaporation of the solvent at room temperature.

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. ORTEPII (Johnson, 1976) plot of the title compound. Displacement ellipsoids are drawn at the 50% level.
	Fig. 2. Packing diagram of the title compound. Water molecules were excluded for clarity.
	Fig. 3. A part of the extensive three-dimensional H-bond network. H-bonds are depicted as dashed lines.

Bis(2,4,6-triamino-1,3,5-triazin-1-ium) bis(4-hydroxypyridine-2,6-carboxylato)cuprate(II) hexahydrate top

Crystal data top

(C₃H₇N₆)₂[Cu(C₇H₃NO₅)₂]·6H₂O	F(000) = 1628
M_r = 788.14	D_x = 1.676 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.2894 (3) Å	Cell parameters from 4074 reflections
b = 37.7699 (12) Å	θ = 2.4–24.5°
c = 7.3414 (2) Å	µ = 0.80 mm⁻¹
β = 94.016 (2)°	T = 293 K
V = 3122.68 (15) Å³	Prism, green
Z = 4	0.28 × 0.20 × 0.10 mm

Data collection top

Bruker APEX CCD area-detector diffractometer	7390 independent reflections
Radiation source: fine-focus sealed tube	5112 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.054
ϕ and ω scans	θ_max = 28.3°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	h = −15→14
T_min = 0.714, T_max = 0.919	k = −50→50
22082 measured reflections	l = −7→9

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0572P)² + 0.0192P] where P = (F_o² + 2F_c²)/3
7390 reflections	(Δ/σ)_max = 0.014
508 parameters	Δρ_max = 0.44 e Å⁻³
13 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

(C₃H₇N₆)₂[Cu(C₇H₃NO₅)₂]·6H₂O	V = 3122.68 (15) Å³
M_r = 788.14	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.2894 (3) Å	µ = 0.80 mm⁻¹
b = 37.7699 (12) Å	T = 293 K
c = 7.3414 (2) Å	0.28 × 0.20 × 0.10 mm
β = 94.016 (2)°

Data collection top

Bruker APEX CCD area-detector diffractometer	7390 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2000)	5112 reflections with I > 2σ(I)
T_min = 0.714, T_max = 0.919	R_int = 0.054
22082 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	13 restraints
wR(F²) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.44 e Å⁻³
7390 reflections	Δρ_min = −0.46 e Å⁻³
508 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
Cu1	0.43767 (3)	0.864573 (8)	0.43487 (5)	0.02540 (10)
O1A	0.62393 (18)	0.71521 (5)	0.5449 (3)	0.0339 (5)
H1A	0.584 (3)	0.7012 (9)	0.503 (5)	0.051*
O1B	0.31432 (19)	1.01748 (5)	0.5212 (3)	0.0363 (5)
H1B	0.335 (3)	1.0291 (9)	0.446 (5)	0.054*
O2A	0.26377 (16)	0.77504 (5)	0.2033 (3)	0.0382 (5)
O2B	0.5124 (2)	0.93825 (6)	0.0457 (3)	0.0532 (7)
O3A	0.29856 (16)	0.83148 (5)	0.2762 (3)	0.0321 (4)
O3B	0.50694 (17)	0.88676 (5)	0.1949 (3)	0.0339 (5)
O4A	0.75786 (16)	0.83882 (5)	0.7359 (3)	0.0356 (5)
O4B	0.2249 (2)	0.89919 (5)	0.8309 (3)	0.0524 (7)
O5A	0.61471 (17)	0.87161 (5)	0.5943 (3)	0.0368 (5)
O5B	0.32894 (17)	0.86291 (5)	0.6639 (3)	0.0313 (4)
N1A	0.50099 (18)	0.81629 (5)	0.4577 (3)	0.0218 (4)
N1B	0.38376 (18)	0.91274 (5)	0.4434 (3)	0.0235 (5)
C1A	0.6033 (2)	0.80997 (6)	0.5575 (4)	0.0218 (5)
C1B	0.3243 (2)	0.92336 (7)	0.5850 (4)	0.0255 (6)
C2A	0.6461 (2)	0.77631 (6)	0.5867 (4)	0.0245 (6)
H2A	0.7177	0.7726	0.6548	0.029*
C2B	0.2994 (2)	0.95844 (7)	0.6138 (4)	0.0299 (6)
H2B	0.2580	0.9655	0.7129	0.036*
C3A	0.5813 (2)	0.74770 (6)	0.5132 (4)	0.0239 (5)
C3B	0.3381 (2)	0.98330 (6)	0.4897 (4)	0.0272 (6)
C4A	0.4744 (2)	0.75443 (7)	0.4131 (4)	0.0248 (6)
H4A	0.4283	0.7358	0.3646	0.030*
C4B	0.3979 (2)	0.97189 (7)	0.3412 (4)	0.0272 (6)
H4B	0.4226	0.9880	0.2558	0.033*
C5A	0.4376 (2)	0.78907 (6)	0.3866 (4)	0.0222 (5)
C5B	0.4196 (2)	0.93624 (7)	0.3236 (4)	0.0249 (6)
C6A	0.3237 (2)	0.79909 (7)	0.2795 (4)	0.0257 (6)
C6B	0.4848 (2)	0.91968 (7)	0.1720 (4)	0.0303 (6)
C7A	0.6650 (2)	0.84270 (6)	0.6363 (4)	0.0250 (6)
C7B	0.2893 (2)	0.89329 (7)	0.7058 (4)	0.0305 (6)
N3A	0.0763 (2)	0.99122 (6)	0.2789 (3)	0.0325 (5)
N4A	0.1682 (2)	0.99282 (6)	−0.0069 (3)	0.0342 (6)
N5A	0.1108 (2)	1.04478 (6)	0.1332 (4)	0.0341 (6)
H5A	0.099 (3)	1.0648 (7)	0.133 (5)	0.041*
N6A	0.1337 (2)	0.94103 (6)	0.1355 (4)	0.0390 (6)
H7	0.1647	0.9304	0.0467	0.047*
H8	0.1079	0.9289	0.2237	0.047*
N7A	0.1989 (2)	1.04682 (7)	−0.1378 (4)	0.0460 (7)
H11	0.2294	1.0367	−0.2284	0.055*
H12	0.1934	1.0695	−0.1344	0.055*
N8A	0.0229 (2)	1.04431 (7)	0.4041 (4)	0.0476 (7)
H9	−0.0045	1.0334	0.4949	0.057*
H10	0.0195	1.0670	0.3983	0.057*
C8A	0.1257 (2)	0.97605 (7)	0.1365 (4)	0.0306 (6)
C9A	0.1607 (2)	1.02764 (7)	−0.0048 (4)	0.0342 (7)
C10A	0.0699 (2)	1.02625 (7)	0.2739 (4)	0.0336 (7)
N3B	0.88638 (18)	0.76048 (6)	0.3504 (3)	0.0289 (5)
N4B	1.0116 (2)	0.80888 (6)	0.4584 (3)	0.0321 (5)
N5B	1.06806 (18)	0.75026 (6)	0.5151 (3)	0.0266 (5)
H5B	1.114 (2)	0.7379 (7)	0.567 (4)	0.032*
N6B	0.8337 (2)	0.81741 (6)	0.2915 (4)	0.0395 (6)
H5	0.7703	0.8094	0.2338	0.047*
H6	0.8458	0.8399	0.2990	0.047*
N7B	1.1849 (2)	0.79554 (6)	0.6287 (3)	0.0347 (6)
H1	1.2006	0.8177	0.6442	0.042*
H2	1.2329	0.7798	0.6758	0.042*
N8B	0.95084 (19)	0.70392 (6)	0.4094 (3)	0.0330 (6)
H3	0.8879	0.6957	0.3518	0.040*
H4	1.0036	0.6897	0.4577	0.040*
C8B	0.9664 (2)	0.73824 (7)	0.4237 (4)	0.0255 (6)
C9B	1.0871 (2)	0.78572 (7)	0.5325 (4)	0.0262 (6)
C10B	0.9134 (2)	0.79486 (7)	0.3697 (4)	0.0286 (6)
O6	0.6260 (2)	0.93858 (5)	0.7253 (3)	0.0433 (6)
H61	0.620 (3)	0.9180 (6)	0.684 (5)	0.065*
H62	0.580 (3)	0.9381 (10)	0.805 (4)	0.065*
O7	0.4746 (2)	0.83354 (6)	0.9426 (3)	0.0472 (6)
H71	0.469 (3)	0.8491 (8)	1.020 (4)	0.071*
H72	0.429 (3)	0.8401 (10)	0.857 (4)	0.071*
O8	0.1197 (2)	0.84896 (6)	0.0289 (4)	0.0508 (6)
H81	0.150 (3)	0.8641 (9)	−0.041 (5)	0.076*
H82	0.168 (3)	0.8391 (10)	0.104 (5)	0.076*
O9	0.7422 (2)	0.87866 (6)	0.0878 (4)	0.0527 (6)
H91	0.672 (2)	0.8828 (11)	0.127 (6)	0.079*
H92	0.750 (4)	0.8675 (10)	−0.015 (4)	0.079*
O10	0.9382 (2)	0.88564 (6)	0.7704 (5)	0.0662 (8)
H101	0.984 (4)	0.8704 (10)	0.821 (6)	0.099*
H102	0.894 (4)	0.8820 (13)	0.864 (5)	0.099*
O11	0.0445 (5)	0.88589 (8)	0.3782 (7)	0.1234 (17)
H111	0.030 (7)	0.878 (2)	0.481 (5)	0.185*
H112	0.088 (6)	0.8685 (13)	0.362 (12)	0.185*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cu1	0.02778 (17)	0.01879 (16)	0.0296 (2)	0.00051 (12)	0.00170 (13)	−0.00093 (13)
O1A	0.0396 (12)	0.0164 (9)	0.0439 (13)	0.0007 (8)	−0.0101 (9)	−0.0015 (8)
O1B	0.0498 (12)	0.0172 (10)	0.0435 (14)	0.0027 (8)	0.0149 (10)	0.0008 (8)
O2A	0.0343 (11)	0.0276 (10)	0.0501 (14)	−0.0027 (8)	−0.0156 (10)	−0.0076 (9)
O2B	0.0761 (16)	0.0373 (12)	0.0501 (16)	0.0082 (11)	0.0337 (13)	0.0108 (11)
O3A	0.0336 (10)	0.0225 (9)	0.0390 (13)	0.0026 (8)	−0.0065 (9)	0.0010 (8)
O3B	0.0428 (11)	0.0214 (10)	0.0382 (13)	0.0037 (8)	0.0069 (10)	−0.0046 (8)
O4A	0.0291 (10)	0.0250 (10)	0.0502 (14)	−0.0024 (8)	−0.0150 (9)	−0.0037 (9)
O4B	0.0794 (16)	0.0281 (11)	0.0549 (16)	0.0079 (10)	0.0410 (14)	0.0079 (10)
O5A	0.0377 (11)	0.0191 (9)	0.0518 (14)	0.0035 (8)	−0.0100 (10)	−0.0060 (9)
O5B	0.0417 (11)	0.0202 (9)	0.0323 (12)	0.0045 (8)	0.0037 (9)	0.0014 (8)
N1A	0.0245 (11)	0.0182 (10)	0.0227 (12)	0.0002 (8)	0.0017 (9)	−0.0011 (8)
N1B	0.0254 (11)	0.0198 (10)	0.0254 (13)	0.0028 (8)	0.0027 (9)	0.0027 (9)
C1A	0.0229 (12)	0.0201 (12)	0.0224 (15)	0.0000 (9)	0.0015 (10)	−0.0030 (10)
C1B	0.0246 (12)	0.0234 (13)	0.0287 (16)	0.0009 (10)	0.0038 (11)	0.0015 (11)
C2A	0.0220 (12)	0.0212 (12)	0.0302 (16)	0.0006 (9)	0.0000 (11)	−0.0023 (11)
C2B	0.0301 (14)	0.0250 (13)	0.0351 (17)	0.0031 (11)	0.0067 (12)	0.0001 (12)
C3A	0.0292 (13)	0.0183 (12)	0.0245 (15)	0.0009 (10)	0.0030 (11)	−0.0001 (10)
C3B	0.0262 (13)	0.0193 (12)	0.0360 (17)	0.0021 (10)	0.0019 (12)	0.0022 (11)
C4A	0.0262 (13)	0.0190 (12)	0.0289 (16)	−0.0027 (10)	−0.0002 (11)	−0.0036 (10)
C4B	0.0276 (13)	0.0224 (13)	0.0318 (17)	−0.0022 (10)	0.0037 (12)	0.0043 (11)
C5A	0.0229 (12)	0.0206 (12)	0.0232 (15)	−0.0019 (9)	0.0012 (11)	−0.0022 (10)
C5B	0.0245 (13)	0.0226 (13)	0.0275 (16)	0.0005 (10)	0.0017 (11)	0.0003 (11)
C6A	0.0271 (13)	0.0246 (13)	0.0253 (16)	−0.0013 (10)	0.0012 (11)	0.0010 (11)
C6B	0.0327 (14)	0.0274 (14)	0.0311 (17)	−0.0013 (11)	0.0051 (12)	−0.0003 (12)
C7A	0.0260 (13)	0.0176 (12)	0.0314 (16)	−0.0025 (10)	0.0029 (11)	−0.0035 (10)
C7B	0.0362 (15)	0.0222 (13)	0.0335 (18)	0.0020 (11)	0.0044 (13)	0.0031 (11)
N3A	0.0371 (13)	0.0240 (12)	0.0367 (15)	0.0024 (10)	0.0031 (11)	−0.0027 (10)
N4A	0.0379 (13)	0.0278 (12)	0.0371 (16)	0.0018 (10)	0.0047 (11)	−0.0040 (10)
N5A	0.0375 (13)	0.0211 (11)	0.0445 (16)	−0.0004 (10)	0.0073 (12)	−0.0027 (11)
N6A	0.0495 (15)	0.0254 (12)	0.0430 (17)	0.0028 (10)	0.0098 (13)	−0.0018 (11)
N7A	0.0574 (17)	0.0341 (14)	0.0485 (18)	−0.0038 (12)	0.0171 (14)	−0.0009 (13)
N8A	0.0653 (18)	0.0277 (13)	0.0522 (19)	0.0046 (12)	0.0208 (15)	−0.0060 (12)
C8A	0.0267 (14)	0.0267 (14)	0.0375 (18)	0.0016 (11)	−0.0036 (12)	−0.0017 (12)
C9A	0.0279 (14)	0.0334 (15)	0.0410 (19)	−0.0029 (11)	0.0008 (13)	−0.0005 (13)
C10A	0.0313 (14)	0.0299 (15)	0.0396 (19)	−0.0003 (11)	0.0022 (13)	−0.0051 (13)
N3B	0.0258 (11)	0.0269 (12)	0.0334 (14)	0.0040 (9)	−0.0026 (10)	0.0041 (10)
N4B	0.0325 (12)	0.0230 (11)	0.0409 (15)	0.0012 (9)	0.0030 (11)	0.0018 (10)
N5B	0.0228 (11)	0.0196 (11)	0.0364 (15)	0.0029 (8)	−0.0044 (10)	0.0044 (9)
N6B	0.0369 (13)	0.0314 (13)	0.0493 (17)	0.0109 (10)	−0.0036 (12)	0.0092 (12)
N7B	0.0344 (13)	0.0228 (12)	0.0458 (17)	−0.0043 (10)	−0.0054 (11)	−0.0004 (10)
N8B	0.0282 (12)	0.0222 (11)	0.0469 (17)	−0.0009 (9)	−0.0087 (11)	0.0000 (10)
C8B	0.0223 (12)	0.0265 (14)	0.0280 (16)	−0.0016 (10)	0.0032 (11)	0.0007 (11)
C9B	0.0260 (13)	0.0231 (13)	0.0296 (16)	−0.0020 (10)	0.0036 (11)	0.0012 (11)
C10B	0.0296 (14)	0.0273 (14)	0.0293 (16)	0.0039 (11)	0.0041 (12)	0.0043 (11)
O6	0.0679 (16)	0.0225 (10)	0.0415 (15)	−0.0086 (10)	0.0179 (11)	−0.0008 (10)
O7	0.0685 (16)	0.0315 (12)	0.0393 (15)	0.0207 (11)	−0.0129 (12)	−0.0065 (10)
O8	0.0402 (13)	0.0409 (13)	0.0688 (19)	−0.0105 (10)	−0.0137 (12)	0.0193 (12)
O9	0.0477 (14)	0.0393 (13)	0.071 (2)	0.0071 (11)	0.0057 (13)	0.0026 (12)
O10	0.0493 (16)	0.0298 (13)	0.119 (3)	−0.0038 (11)	−0.0005 (16)	0.0053 (14)
O11	0.201 (5)	0.0406 (18)	0.139 (4)	−0.011 (2)	0.086 (3)	0.004 (2)

Geometric parameters (Å, º) top

Cu1—N1B	1.921 (2)	N4A—C8A	1.346 (4)
Cu1—N1A	1.962 (2)	N5A—C10A	1.355 (4)
Cu1—O3B	2.147 (2)	N5A—C9A	1.357 (4)
Cu1—O5B	2.1508 (19)	N5A—H5A	0.77 (2)
Cu1—O5A	2.260 (2)	N6A—C8A	1.326 (3)
Cu1—O3A	2.2648 (19)	N6A—H7	0.8600
O1A—C3A	1.333 (3)	N6A—H8	0.8600
O1A—H1A	0.74 (3)	N7A—C9A	1.313 (4)
O1B—C3B	1.342 (3)	N7A—H11	0.8600
O1B—H1B	0.76 (4)	N7A—H12	0.8600
O2A—C6A	1.242 (3)	N8A—C10A	1.316 (4)
O2B—C6B	1.221 (3)	N8A—H9	0.8600
O3A—C6A	1.256 (3)	N8A—H10	0.8600
O3B—C6B	1.277 (3)	N3B—C8B	1.321 (3)
O4A—C7A	1.244 (3)	N3B—C10B	1.339 (3)
O4B—C7B	1.231 (3)	N4B—C9B	1.312 (3)
O5A—C7A	1.259 (3)	N4B—C10B	1.353 (4)
O5B—C7B	1.277 (3)	N5B—C9B	1.361 (3)
N1A—C5A	1.338 (3)	N5B—C8B	1.365 (3)
N1A—C1A	1.345 (3)	N5B—H5B	0.78 (2)
N1B—C5B	1.332 (3)	N6B—C10B	1.339 (3)
N1B—C1B	1.338 (3)	N6B—H5	0.8600
C1A—C2A	1.372 (3)	N6B—H6	0.8600
C1A—C7A	1.514 (3)	N7B—C9B	1.322 (3)
C1B—C2B	1.374 (4)	N7B—H1	0.8600
C1B—C7B	1.510 (4)	N7B—H2	0.8600
C2A—C3A	1.393 (3)	N8B—C8B	1.311 (3)
C2A—H2A	0.9300	N8B—H3	0.8600
C2B—C3B	1.400 (4)	N8B—H4	0.8600
C2B—H2B	0.9300	O6—H61	0.834 (18)
C3A—C4A	1.391 (4)	O6—H62	0.808 (18)
C3B—C4B	1.390 (4)	O7—H71	0.821 (18)
C4A—C5A	1.382 (3)	O7—H72	0.821 (19)
C4A—H4A	0.9300	O8—H81	0.86 (4)
C4B—C5B	1.377 (3)	O8—H82	0.84 (4)
C4B—H4B	0.9300	O9—H91	0.877 (18)
C5A—C6A	1.507 (4)	O9—H92	0.876 (19)
C5B—C6B	1.512 (4)	O10—H101	0.84 (4)
N3A—C10A	1.325 (3)	O10—H102	0.89 (4)
N3A—C8A	1.347 (4)	O11—H111	0.85 (2)
N4A—C9A	1.318 (3)	O11—H112	0.83 (6)

N1B—Cu1—N1A	172.83 (10)	O2B—C6B—C5B	119.0 (2)
N1B—Cu1—O3B	77.96 (8)	O3B—C6B—C5B	114.0 (2)
N1A—Cu1—O3B	106.34 (8)	O4A—C7A—O5A	126.4 (2)
N1B—Cu1—O5B	78.63 (8)	O4A—C7A—C1A	118.3 (2)
N1A—Cu1—O5B	97.51 (8)	O5A—C7A—C1A	115.3 (2)
O3B—Cu1—O5B	155.97 (7)	O4B—C7B—O5B	125.3 (3)
N1B—Cu1—O5A	98.19 (8)	O4B—C7B—C1B	119.6 (2)
N1A—Cu1—O5A	76.19 (8)	O5B—C7B—C1B	115.1 (2)
O3B—Cu1—O5A	91.11 (8)	C10A—N3A—C8A	115.3 (2)
O5B—Cu1—O5A	97.53 (8)	C9A—N4A—C8A	115.7 (2)
N1B—Cu1—O3A	109.24 (8)	C10A—N5A—C9A	120.3 (2)
N1A—Cu1—O3A	76.48 (8)	C10A—N5A—H5A	116 (2)
O3B—Cu1—O3A	94.16 (7)	C9A—N5A—H5A	123 (2)
O5B—Cu1—O3A	88.44 (7)	C8A—N6A—H7	120.0
O5A—Cu1—O3A	152.56 (6)	C8A—N6A—H8	120.0
C3A—O1A—H1A	112 (3)	H7—N6A—H8	120.0
C3B—O1B—H1B	111 (3)	C9A—N7A—H11	120.0
C6A—O3A—Cu1	112.32 (16)	C9A—N7A—H12	120.0
C6B—O3B—Cu1	114.11 (17)	H11—N7A—H12	120.0
C7A—O5A—Cu1	113.08 (16)	C10A—N8A—H9	120.0
C7B—O5B—Cu1	113.01 (17)	C10A—N8A—H10	120.0
C5A—N1A—C1A	119.4 (2)	H9—N8A—H10	120.0
C5A—N1A—Cu1	119.96 (17)	N6A—C8A—N4A	115.9 (3)
C1A—N1A—Cu1	120.37 (16)	N6A—C8A—N3A	117.4 (3)
C5B—N1B—C1B	120.4 (2)	N4A—C8A—N3A	126.7 (2)
C5B—N1B—Cu1	119.86 (17)	N7A—C9A—N4A	121.1 (3)
C1B—N1B—Cu1	119.10 (17)	N7A—C9A—N5A	117.8 (3)
N1A—C1A—C2A	122.0 (2)	N4A—C9A—N5A	121.0 (3)
N1A—C1A—C7A	114.7 (2)	N8A—C10A—N3A	121.4 (3)
C2A—C1A—C7A	123.3 (2)	N8A—C10A—N5A	117.5 (3)
N1B—C1B—C2B	121.9 (2)	N3A—C10A—N5A	121.0 (3)
N1B—C1B—C7B	113.4 (2)	C8B—N3B—C10B	115.4 (2)
C2B—C1B—C7B	124.7 (2)	C9B—N4B—C10B	115.2 (2)
C1A—C2A—C3A	119.2 (2)	C9B—N5B—C8B	119.7 (2)
C1A—C2A—H2A	120.4	C9B—N5B—H5B	117 (2)
C3A—C2A—H2A	120.4	C8B—N5B—H5B	123 (2)
C1B—C2B—C3B	118.0 (2)	C10B—N6B—H5	120.0
C1B—C2B—H2B	121.0	C10B—N6B—H6	120.0
C3B—C2B—H2B	121.0	H5—N6B—H6	120.0
O1A—C3A—C4A	123.4 (2)	C9B—N7B—H1	120.0
O1A—C3A—C2A	118.2 (2)	C9B—N7B—H2	120.0
C4A—C3A—C2A	118.4 (2)	H1—N7B—H2	120.0
O1B—C3B—C4B	123.2 (2)	C8B—N8B—H3	120.0
O1B—C3B—C2B	117.2 (2)	C8B—N8B—H4	120.0
C4B—C3B—C2B	119.6 (2)	H3—N8B—H4	120.0
C5A—C4A—C3A	119.2 (2)	N8B—C8B—N3B	120.8 (2)
C5A—C4A—H4A	120.4	N8B—C8B—N5B	118.1 (2)
C3A—C4A—H4A	120.4	N3B—C8B—N5B	121.1 (2)
C5B—C4B—C3B	118.5 (2)	N4B—C9B—N7B	121.9 (2)
C5B—C4B—H4B	120.8	N4B—C9B—N5B	121.5 (2)
C3B—C4B—H4B	120.8	N7B—C9B—N5B	116.5 (2)
N1A—C5A—C4A	121.7 (2)	N3B—C10B—N6B	115.5 (3)
N1A—C5A—C6A	115.1 (2)	N3B—C10B—N4B	127.1 (2)
C4A—C5A—C6A	123.2 (2)	N6B—C10B—N4B	117.4 (2)
N1B—C5B—C4B	121.7 (2)	H61—O6—H62	101 (3)
N1B—C5B—C6B	113.4 (2)	H71—O7—H72	104 (4)
C4B—C5B—C6B	125.0 (2)	H81—O8—H82	116 (4)
O2A—C6A—O3A	126.0 (3)	H91—O9—H92	121 (4)
O2A—C6A—C5A	118.0 (2)	H101—O10—H102	85 (4)
O3A—C6A—C5A	116.0 (2)	H111—O11—H112	89 (6)
O2B—C6B—O3B	126.9 (3)

N1B—Cu1—O3A—C6A	−174.06 (18)	C1A—N1A—C5A—C4A	0.1 (4)
N1A—Cu1—O3A—C6A	1.43 (18)	Cu1—N1A—C5A—C4A	−174.41 (19)
O3B—Cu1—O3A—C6A	107.24 (18)	C1A—N1A—C5A—C6A	179.2 (2)
O5B—Cu1—O3A—C6A	−96.68 (18)	Cu1—N1A—C5A—C6A	4.7 (3)
O5A—Cu1—O3A—C6A	6.7 (3)	C3A—C4A—C5A—N1A	−1.3 (4)
N1B—Cu1—O3B—C6B	1.61 (19)	C3A—C4A—C5A—C6A	179.7 (2)
N1A—Cu1—O3B—C6B	−172.46 (19)	C1B—N1B—C5B—C4B	0.4 (4)
O5B—Cu1—O3B—C6B	14.9 (3)	Cu1—N1B—C5B—C4B	−170.2 (2)
O5A—Cu1—O3B—C6B	−96.53 (19)	C1B—N1B—C5B—C6B	−179.7 (2)
O3A—Cu1—O3B—C6B	110.41 (19)	Cu1—N1B—C5B—C6B	9.8 (3)
N1B—Cu1—O5A—C7A	169.77 (19)	C3B—C4B—C5B—N1B	0.8 (4)
N1A—Cu1—O5A—C7A	−5.67 (19)	C3B—C4B—C5B—C6B	−179.2 (3)
O3B—Cu1—O5A—C7A	−112.23 (19)	Cu1—O3A—C6A—O2A	−179.5 (2)
O5B—Cu1—O5A—C7A	90.25 (19)	Cu1—O3A—C6A—C5A	0.5 (3)
O3A—Cu1—O5A—C7A	−11.0 (3)	N1A—C5A—C6A—O2A	176.8 (2)
N1B—Cu1—O5B—C7B	−5.00 (19)	C4A—C5A—C6A—O2A	−4.1 (4)
N1A—Cu1—O5B—C7B	168.87 (19)	N1A—C5A—C6A—O3A	−3.2 (3)
O3B—Cu1—O5B—C7B	−18.3 (3)	C4A—C5A—C6A—O3A	175.9 (2)
O5A—Cu1—O5B—C7B	91.90 (19)	Cu1—O3B—C6B—O2B	−178.7 (3)
O3A—Cu1—O5B—C7B	−114.98 (19)	Cu1—O3B—C6B—C5B	2.8 (3)
N1B—Cu1—N1A—C5A	140.1 (6)	N1B—C5B—C6B—O2B	173.5 (3)
O3B—Cu1—N1A—C5A	−93.80 (19)	C4B—C5B—C6B—O2B	−6.5 (4)
O5B—Cu1—N1A—C5A	83.18 (19)	N1B—C5B—C6B—O3B	−7.8 (3)
O5A—Cu1—N1A—C5A	179.1 (2)	C4B—C5B—C6B—O3B	172.1 (3)
O3A—Cu1—N1A—C5A	−3.38 (18)	Cu1—O5A—C7A—O4A	−173.7 (2)
N1B—Cu1—N1A—C1A	−34.3 (8)	Cu1—O5A—C7A—C1A	5.5 (3)
O3B—Cu1—N1A—C1A	91.79 (19)	N1A—C1A—C7A—O4A	177.3 (2)
O5B—Cu1—N1A—C1A	−91.23 (19)	C2A—C1A—C7A—O4A	−1.6 (4)
O5A—Cu1—N1A—C1A	4.72 (18)	N1A—C1A—C7A—O5A	−2.0 (3)
O3A—Cu1—N1A—C1A	−177.8 (2)	C2A—C1A—C7A—O5A	179.1 (2)
N1A—Cu1—N1B—C5B	121.0 (6)	Cu1—O5B—C7B—O4B	179.7 (3)
O3B—Cu1—N1B—C5B	−6.50 (19)	Cu1—O5B—C7B—C1B	1.3 (3)
O5B—Cu1—N1B—C5B	179.0 (2)	N1B—C1B—C7B—O4B	−173.3 (3)
O5A—Cu1—N1B—C5B	82.9 (2)	C2B—C1B—C7B—O4B	6.8 (5)
O3A—Cu1—N1B—C5B	−96.7 (2)	N1B—C1B—C7B—O5B	5.2 (4)
N1A—Cu1—N1B—C1B	−49.6 (7)	C2B—C1B—C7B—O5B	−174.7 (3)
O3B—Cu1—N1B—C1B	−177.1 (2)	C9A—N4A—C8A—N6A	−179.6 (3)
O5B—Cu1—N1B—C1B	8.34 (19)	C9A—N4A—C8A—N3A	0.4 (4)
O5A—Cu1—N1B—C1B	−87.8 (2)	C10A—N3A—C8A—N6A	−179.8 (3)
O3A—Cu1—N1B—C1B	92.6 (2)	C10A—N3A—C8A—N4A	0.1 (4)
C5A—N1A—C1A—C2A	1.1 (4)	C8A—N4A—C9A—N7A	−179.7 (3)
Cu1—N1A—C1A—C2A	175.49 (19)	C8A—N4A—C9A—N5A	−1.2 (4)
C5A—N1A—C1A—C7A	−177.9 (2)	C10A—N5A—C9A—N7A	180.0 (3)
Cu1—N1A—C1A—C7A	−3.5 (3)	C10A—N5A—C9A—N4A	1.4 (4)
C5B—N1B—C1B—C2B	−0.7 (4)	C8A—N3A—C10A—N8A	179.5 (3)
Cu1—N1B—C1B—C2B	169.8 (2)	C8A—N3A—C10A—N5A	0.0 (4)
C5B—N1B—C1B—C7B	179.4 (2)	C9A—N5A—C10A—N8A	179.7 (3)
Cu1—N1B—C1B—C7B	−10.0 (3)	C9A—N5A—C10A—N3A	−0.8 (4)
N1A—C1A—C2A—C3A	−0.9 (4)	C10B—N3B—C8B—N8B	−178.3 (2)
C7A—C1A—C2A—C3A	178.0 (2)	C10B—N3B—C8B—N5B	1.1 (4)
N1B—C1B—C2B—C3B	0.0 (4)	C9B—N5B—C8B—N8B	−180.0 (2)
C7B—C1B—C2B—C3B	179.9 (3)	C9B—N5B—C8B—N3B	0.5 (4)
C1A—C2A—C3A—O1A	−179.3 (2)	C10B—N4B—C9B—N7B	−177.6 (2)
C1A—C2A—C3A—C4A	−0.3 (4)	C10B—N4B—C9B—N5B	1.9 (4)
C1B—C2B—C3B—O1B	−179.1 (2)	C8B—N5B—C9B—N4B	−2.2 (4)
C1B—C2B—C3B—C4B	1.2 (4)	C8B—N5B—C9B—N7B	177.4 (2)
O1A—C3A—C4A—C5A	−179.7 (2)	C8B—N3B—C10B—N6B	178.4 (2)
C2A—C3A—C4A—C5A	1.4 (4)	C8B—N3B—C10B—N4B	−1.5 (4)
O1B—C3B—C4B—C5B	178.8 (3)	C9B—N4B—C10B—N3B	0.0 (4)
C2B—C3B—C4B—C5B	−1.5 (4)	C9B—N4B—C10B—N6B	−179.9 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O7ⁱ	0.74 (3)	1.84 (3)	2.573 (3)	169 (4)
O1B—H1B···O6ⁱⁱ	0.76 (4)	1.83 (4)	2.579 (3)	173 (4)
N5A—H5A···O10ⁱⁱ	0.77 (2)	2.06 (3)	2.787 (3)	159 (3)
N6A—H7···O4Bⁱⁱⁱ	0.86	2.13	2.980 (3)	173
N6A—H8···O11	0.86	2.13	2.962 (4)	162
N7A—H11···O1Bⁱⁱⁱ	0.86	2.25	3.106 (3)	172
N7A—H12···O9^iv	0.86	2.11	2.910 (4)	155
N8A—H9···N3A^v	0.86	2.11	2.973 (4)	177
N8A—H10···O10ⁱⁱ	0.86	2.25	2.986 (4)	144
N8A—H10···O11^v	0.86	2.56	3.202 (4)	133
N5B—H5B···O2A^vi	0.78 (2)	1.96 (3)	2.698 (3)	157 (3)
N6B—H5···O1Aⁱ	0.86	2.28	3.131 (3)	170
N6B—H6···O9	0.86	2.38	2.905 (3)	120
N7B—H1···O5B^vii	0.86	2.24	3.021 (3)	151
N7B—H2···O2A^vi	0.86	2.11	2.852 (3)	144
N8B—H3···O4Aⁱ	0.86	2.10	2.930 (3)	163
N8B—H4···O8^vi	0.86	2.01	2.857 (3)	169
O6—H61···O5A	0.83 (2)	1.87 (2)	2.706 (3)	177 (4)
O6—H62···O2B^viii	0.81 (2)	1.97 (2)	2.756 (3)	163 (4)
O7—H71···O3B^viii	0.82 (2)	1.94 (2)	2.741 (3)	163 (4)
O7—H72···O5B	0.82 (2)	1.95 (2)	2.766 (3)	171 (4)
O8—H81···O4Bⁱⁱⁱ	0.86 (2)	1.86 (2)	2.714 (3)	173 (4)
O8—H82···O3A	0.83 (2)	1.90 (2)	2.701 (3)	162 (4)
O9—H91···O3B	0.88 (2)	1.97 (2)	2.839 (3)	172 (4)
O9—H92···O4Aⁱⁱⁱ	0.88 (2)	2.13 (2)	3.005 (3)	176 (4)
O10—H101···O8^ix	0.84 (4)	2.24 (3)	3.030 (4)	157 (5)
O10—H102···O4A	0.89 (4)	2.39 (5)	2.695 (3)	101 (4)
O11—H111···O10^x	0.85 (2)	2.44 (4)	3.196 (5)	149 (7)
O11—H112···N4B^x	0.83 (6)	2.53 (7)	2.996 (4)	116 (6)
O11—H112···O8	0.83 (6)	2.60 (8)	3.090 (5)	118 (7)

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

Experimental details

Crystal data
Chemical formula	(C₃H₇N₆)₂[Cu(C₇H₃NO₅)₂]·6H₂O
M_r	788.14
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.2894 (3), 37.7699 (12), 7.3414 (2)
β (°)	94.016 (2)
V (Å³)	3122.68 (15)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.80
Crystal size (mm)	0.28 × 0.20 × 0.10

Data collection
Diffractometer	Bruker APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2000)
T_min, T_max	0.714, 0.919
No. of measured, independent and observed [I > 2σ(I)] reflections	22082, 7390, 5112
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.116, 1.03
No. of reflections	7390
No. of parameters	508
No. of restraints	13
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.46

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPII (Johnson, 1976).

Selected bond angles (º) top

C10A—N3A—C8A	115.3 (2)	C8B—N3B—C10B	115.4 (2)
C9A—N4A—C8A	115.7 (2)	C9B—N4B—C10B	115.2 (2)
C10A—N5A—C9A	120.3 (2)	C9B—N5B—C8B	119.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1A—H1A···O7ⁱ	0.74 (3)	1.84 (3)	2.573 (3)	169 (4)
O1B—H1B···O6ⁱⁱ	0.76 (4)	1.83 (4)	2.579 (3)	173 (4)
N5A—H5A···O10ⁱⁱ	0.77 (2)	2.06 (3)	2.787 (3)	159 (3)
N6A—H7···O4Bⁱⁱⁱ	0.86	2.13	2.980 (3)	172.8
N6A—H8···O11	0.86	2.13	2.962 (4)	161.6
N7A—H11···O1Bⁱⁱⁱ	0.86	2.25	3.106 (3)	172.4
N7A—H12···O9^iv	0.86	2.11	2.910 (4)	154.9
N8A—H9···N3A^v	0.86	2.11	2.973 (4)	177.2
N8A—H10···O10ⁱⁱ	0.86	2.25	2.986 (4)	144.2
N8A—H10···O11^v	0.86	2.56	3.202 (4)	132.5
N5B—H5B···O2A^vi	0.78 (2)	1.96 (3)	2.698 (3)	157 (3)
N6B—H5···O1Aⁱ	0.86	2.28	3.131 (3)	170.0
N6B—H6···O9	0.86	2.38	2.905 (3)	119.8
N7B—H1···O5B^vii	0.86	2.24	3.021 (3)	151.2
N7B—H2···O2A^vi	0.86	2.11	2.852 (3)	144.4
N8B—H3···O4Aⁱ	0.86	2.10	2.930 (3)	162.9
N8B—H4···O8^vi	0.86	2.01	2.857 (3)	169.4
O6—H61···O5A	0.83 (2)	1.87 (2)	2.706 (3)	177 (4)
O6—H62···O2B^viii	0.81 (2)	1.97 (2)	2.756 (3)	163 (4)
O7—H71···O3B^viii	0.82 (2)	1.94 (2)	2.741 (3)	163 (4)
O7—H72···O5B	0.82 (2)	1.95 (2)	2.766 (3)	171 (4)
O8—H81···O4Bⁱⁱⁱ	0.86 (2)	1.86 (2)	2.714 (3)	173 (4)
O8—H82···O3A	0.83 (2)	1.90 (2)	2.701 (3)	162 (4)
O9—H91···O3B	0.88 (2)	1.97 (2)	2.839 (3)	172 (4)
O9—H92···O4Aⁱⁱⁱ	0.88 (2)	2.13 (2)	3.005 (3)	176 (4)
O10—H101···O8^ix	0.84 (4)	2.24 (3)	3.030 (4)	157 (5)
O10—H102···O4A	0.89 (4)	2.39 (5)	2.695 (3)	101 (4)
O11—H111···O10^x	0.85 (2)	2.44 (4)	3.196 (5)	149 (7)
O11—H112···N4B^x	0.83 (6)	2.53 (7)	2.996 (4)	116 (6)
O11—H112···O8	0.83 (6)	2.60 (8)	3.090 (5)	118 (7)

References

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
Aghabozorg, H., Motyeian, E., Soleimannejad, J., Ghadermazi, M. & Attar Gharamaleki, J. (2008). Acta Cryst. E64, m252–m253. Web of Science CSD CrossRef IUCr Journals 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 (2003). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Johnson, C. K. (1976). ORTEPII. Report ORNL-5138. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 64| Part 9| September 2008| Pages m1173-m1174

doi:10.1107/S160053680802566X

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

Bis(2,4,6-tri­amino-1,3,5-triazin-1-ium) bis­­(4-hy­droxy­pyridine-2,6-carboxyl­ato)­cuprate(II) hexa­hydrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

References

metal-organic compounds

Bis(2,4,6-triamino-1,3,5-triazin-1-ium) bis(4-hydroxypyridine-2,6-carboxylato)cuprate(II) hexahydrate