Tetra­kis(2,4,6-triamino-1,3,5-triazin-1-ium) tris­(pyridine-2,6-dicarboxyl­ato)calcate(II) hexa­hydrate

Aghabozorg, H.; Daneshvar, S.; Nemati, A.

doi:10.1107/S1600536808022873

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Pages m1063-m1064

doi:10.1107/S1600536808022873

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Tetrakis(2,4,6-triamino-1,3,5-triazin-1-ium) tris(pyridine-2,6-dicarboxylato)calcate(II) hexahydrate

Hossein Aghabozorg,^a ^* Shirin Daneshvar ^b and Andya Nemati ^a

^aFaculty of Chemistry, Tarbiat Moallem University, Tehran, Iran, and ^bDepartment of Chemistry, Islamic Azad University, Ardabil Branch, Ardabil, Iran
^*Correspondence e-mail: haghabozorg@yahoo.com

(Received 26 June 2008; accepted 21 July 2008; online 26 July 2008)

The title compound, (C₃H₇N₆)₄[Ca(C₇H₃NO₄)₃]·6H₂O or (tataH)₄[Ca(pydc)₃]·6H₂O (where tata is 2,4,6-triamino-1,3,5-triazine and pydcH₂ is pyridine-2,6-dicarboxylic acid), was obtained by reaction of Ca(NO₃)₂·4H₂O with the proton-transfer compound (tataH)₂(pydc) in aqueous solution. The [Ca(pydc)₃]⁴⁻ anion has twofold crystallographic symmetry. It is a nine-coordinate Ca^II complex with a distorted tricapped trigonal-prismatic coordination geometry. The structure also contains four tataH⁺ cations and six uncoordinated water molecules. There are extensive O—H⋯O, O—H⋯N, N—H⋯O, N—H⋯N and C—H⋯O hydrogen bonds in the crystal structure.

Related literature

For related literature, see: Aghabozorg et al. (2006 ); Aghabozorg, Attar Gharamaleki et al. (2008 ); Aghabozorg, Manteghi & Sheshmani (2008 ); Aghajani et al. (2006 ); Sharif et al. (2007 ).

Experimental

Crystal data

(C₃H₇N₆)₄[Ca(C₇H₃NO₄)₃]·6H₂O
M_r = 1152.07
Monoclinic, C 2/c
a = 17.9605 (15) Å
b = 10.1672 (9) Å
c = 25.922 (2) Å
β = 94.467 (2)°
V = 4719.1 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 100 (2) K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.928, T_max = 0.954
16983 measured reflections
6215 independent reflections
4412 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.051
wR(F²) = 0.127
S = 1.09
6215 reflections
365 parameters
H-atom parameters constrained
Δρ_max = 0.51 e Å⁻³
Δρ_min = −0.77 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1W—H1WB⋯O2ⁱ	0.84	1.91	2.710 (3)	160
O1W—H1WA⋯O6ⁱⁱ	0.84	1.92	2.751 (3)	170
O2W—H2WB⋯N4ⁱⁱⁱ	0.84	2.26	3.022 (3)	151
N3—H3N⋯O2	0.88	1.79	2.667 (2)	176
O2W—H2WA⋯O5	0.84	2.05	2.888 (3)	175
O3W—H3WB⋯O2W^iv	0.84	2.18	2.963 (3)	154
O3W—H3WA⋯N14^v	0.84	2.17	3.007 (3)	180
N6—H6NA⋯O1Wⁱ	0.88	2.45	3.294 (3)	162
N6—H6NB⋯O1W	0.88	1.90	2.740 (3)	160
N7—H7NA⋯N11^v	0.88	2.22	3.103 (3)	176
N7—H7NB⋯O2Wⁱⁱ	0.88	2.44	3.205 (3)	146
N7—H7NB⋯O4ⁱⁱ	0.88	2.53	3.111 (2)	124
N8—H8NA⋯O1	0.88	2.07	2.948 (2)	172
N12—H11A⋯N10^vi	0.88	2.23	3.109 (2)	178
N12—H11B⋯O5	0.88	2.32	3.196 (2)	175
N8—H8NB⋯O3W	0.88	2.15	2.832 (4)	134
N9—H9NA⋯O3	0.88	1.89	2.754 (2)	165
N13—H13A⋯O4^vii	0.88	2.08	2.925 (2)	160
N13—H13B⋯O6^vi	0.88	1.96	2.790 (2)	157
N14—H14A⋯O3	0.88	2.39	3.143 (2)	144
N14—H14B⋯N5^viii	0.88	2.10	2.978 (3)	178
C4—H4A⋯O2^ix	0.95	2.55	3.370 (3)	145
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ ; (ii) $[x, -y+1, z-{\script{1\over 2}}]$ ; (iii) $[x, -y+1, z+{\script{1\over 2}}]$ ; (iv) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) $[-x, y+1, -z+{\script{1\over 2}}]$ ; (vi) -x, -y+1, -z+1; (vii) -x, -y, -z+1; (viii) $[-x, y-1, -z+{\script{1\over 2}}]$ ; (ix) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808022873/om2249sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808022873/om2249Isup2.hkl

checkCIF report

Comment top

Hydrogen bonding plays a key role in chemical, catalytic and biochemical processes, as well as in supramolecular chemistry and crystal engineering. Recently we have reported the reaction between the proton-transfer compound, (tataH)₂(pydc) with metal salts Co(NO₃)₂.6H₂O, Bi(NO₃)₃.5H₂O, Zn(NO₃)₂.4H₂O and Cd(NO₃)₂.2H₂O in a 2:1 molar ratio. These reactions lead to the formation of the (tataH)₂[Co(H₂O)₆][Co(pydc)₂]₂.4H₂O (Aghabozorg, Attar Gharamaleki et al., 2008), (tataH)_n [Bi(pydc)₂(H₂O)]_n(Sharif et al., 2007), (tataH)₂ [Zn(pydc)₂].10H₂O (Aghajani et al., 2006) and (tataH)₂ [Cd(pydc)₂] (Aghabozorg, Aghajani et al., 2006) compounds respectively. For more details and related literature see our recent review article (Aghabozorg, Manteghi et al., 2008).

The structure of the title compound is shown in Fig.1. The anion has crystallographic 2-fold symmetry. The compound contains [Ca(pydc)₃]^4– anion, four (tataH)⁺ cations and six uncoordinated water molecules. In the [Ca(pydc)₃]^4– anions, Ca^II atom is nine-coordinated by three N atoms (N1, N1a and N2) and six O atoms (O1, O1a, O3, O3a, O5 and O5a) with the range of 2.5031 (14)–2.5472 (15)Å from the carboxylate groups of three (pydc)^2– groups that act as tridentate ligands. The coordination geometry around the Ca^II atom is distorted tricapped trigonal prism (Fig.2). Three N atoms (N1, N1a and N2) occupying three cap positions and make a flat triangle with N1—Ca1—N1a: 119.78 (8)°, N1—Ca1—N2: 120.11 (4)° and N1a—Ca1—N2: 120.11 (4)° that the sum of these angles is 360.00° and six O atoms (O1, O1a, O3, O3a, O5 and O5a) forming the trigonal prism positions.

There are various hydrogen bonds such as O—H···O, O—H···N, N—H···O and N—H···N [in the range 2.667 (2)–3.294 (3) Å] in this structure (Fig.3) and C—H···O hydrogen bonds [with D···A 3.370 (3) Å] are also present (Table 1). These extensive hydrogen bonds between [Ca(pydc)₃]^4– anions, (tataH)⁺ cations and uncoordinated water molecules play an important role in stabilization of the crystal packing.

Related literature top

For related literature, see: Aghabozorg et al. (2006); Aghabozorg, Attar Gharamaleki et al. (2008); Aghabozorg, Manteghi & Sheshmani (2008); Aghajani et al. (2006); Sharif et al. (2007).

Experimental top

The proton-transfer compound, (tataH)₂(pydc), was prepared by the reaction of pyridine-2,6-dicarboxylic acid (pydcH₂) with 2,4,6-triamino-1,3,5-triazine (tata). The reaction between Ca(NO₃)₂.4H₂O (118 mg, 0.5 mmol) in water (20 ml) and (tataH)₂(pydc) (420 mg, 1.0 mmol) in water (20 ml), in 1:2 molar ratio gave a colorless compound after slow evaporation of the solvent at the room temperature.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 50% probability level. The anion is located on a 2-fold axis and thus, the asymmetric unit contains one half anion, two cations and three water molecules.
	Fig. 2. A view of the distorted tricapped trigonal prism around the Ca^II atom.
	Fig. 3. Crystal packing with hydrogen bonds shown as dashed lines.

Tetrakis(2,4,6-triamino-1,3,5-triazin-1-ium) tris(pyridine-2,6-dicarboxylato)calcate(II) hexahydrate top

Crystal data top

(C₃H₇N₆)₄[Ca(C₇H₃NO₄)₃]·6H₂O	F(000) = 2400
M_r = 1152.07	D_x = 1.622 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 935 reflections
a = 17.9605 (15) Å	θ = 3–29°
b = 10.1672 (9) Å	µ = 0.24 mm⁻¹
c = 25.922 (2) Å	T = 100 K
β = 94.467 (2)°	Prism, colourless
V = 4719.1 (7) Å³	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEXII diffractometer	6215 independent reflections
Radiation source: fine-focus sealed tube	4412 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
ω scans	θ_max = 29.0°, θ_min = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −19→24
T_min = 0.928, T_max = 0.954	k = −13→13
16983 measured reflections	l = −35→35

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.127	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0392P)² + 1P] where P = (F_o² + 2F_c²)/3
6215 reflections	(Δ/σ)_max < 0.001
365 parameters	Δρ_max = 0.51 e Å⁻³
0 restraints	Δρ_min = −0.77 e Å⁻³

Crystal data top

(C₃H₇N₆)₄[Ca(C₇H₃NO₄)₃]·6H₂O	V = 4719.1 (7) Å³
M_r = 1152.07	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 17.9605 (15) Å	µ = 0.24 mm⁻¹
b = 10.1672 (9) Å	T = 100 K
c = 25.922 (2) Å	0.30 × 0.20 × 0.20 mm
β = 94.467 (2)°

Data collection top

Bruker SMART APEXII diffractometer	6215 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4412 reflections with I > 2σ(I)
T_min = 0.928, T_max = 0.954	R_int = 0.031
16983 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.127	H-atom parameters constrained
S = 1.09	Δρ_max = 0.51 e Å⁻³
6215 reflections	Δρ_min = −0.77 e Å⁻³
365 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
Ca1	0.0000	0.32225 (5)	0.2500	0.01468 (13)
C1	0.17008 (12)	0.2206 (2)	0.21823 (8)	0.0189 (4)
N1	0.12161 (10)	0.19798 (16)	0.25401 (6)	0.0167 (3)
O1	0.08882 (8)	0.38891 (14)	0.18496 (5)	0.0198 (3)
O1W	0.25538 (11)	0.3625 (2)	−0.08194 (7)	0.0511 (6)
H1WB	0.2800	0.3196	−0.1025	0.061*
H1WA	0.2150	0.3792	−0.0992	0.061*
O2W	0.20543 (11)	0.3177 (2)	0.38198 (7)	0.0464 (5)
H2WB	0.2093	0.3575	0.4105	0.056*
H2WA	0.1704	0.3502	0.3627	0.056*
O2	0.18167 (9)	0.32683 (15)	0.13789 (6)	0.0225 (3)
N2	0.0000	0.5723 (2)	0.2500	0.0160 (5)
C2	0.23993 (13)	0.1634 (3)	0.21999 (9)	0.0291 (5)
H2A	0.2733	0.1824	0.1943	0.035*
O3W	0.16530 (16)	0.8783 (3)	0.17830 (10)	0.0743 (8)
H3WB	0.2094	0.8677	0.1704	0.089*
H3WA	0.1367	0.9132	0.1550	0.089*
N3	0.16153 (10)	0.53273 (18)	0.07458 (7)	0.0222 (4)
H3N	0.1666	0.4663	0.0963	0.027*
O3	0.02261 (8)	0.15716 (14)	0.32346 (5)	0.0203 (3)
C3	0.26030 (14)	0.0777 (3)	0.26017 (9)	0.0345 (6)
H3A	0.3079	0.0366	0.2624	0.041*
O4	0.10324 (9)	0.02965 (15)	0.37134 (6)	0.0252 (3)
C4	0.21035 (14)	0.0525 (2)	0.29714 (9)	0.0292 (5)
H4A	0.2230	−0.0063	0.3249	0.035*
N4	0.18475 (10)	0.62366 (18)	−0.00573 (7)	0.0217 (4)
O5	0.08073 (9)	0.43271 (14)	0.32086 (6)	0.0220 (3)
C5	0.14127 (12)	0.1153 (2)	0.29278 (8)	0.0183 (4)
N5	0.12433 (10)	0.75024 (17)	0.05810 (7)	0.0207 (4)
N6	0.22996 (11)	0.41835 (19)	0.01860 (8)	0.0275 (4)
H6NA	0.2338	0.3554	0.0419	0.033*
H6NB	0.2477	0.4118	−0.0120	0.033*
O6	0.11801 (9)	0.61386 (15)	0.36402 (6)	0.0236 (3)
C6	0.14421 (12)	0.3194 (2)	0.17714 (7)	0.0174 (4)
N7	0.13887 (10)	0.83102 (18)	−0.02277 (7)	0.0224 (4)
H7NA	0.1188	0.9049	−0.0129	0.027*
H7NB	0.1526	0.8246	−0.0545	0.027*
C7	0.08494 (12)	0.09839 (19)	0.33279 (8)	0.0171 (4)
N8	0.09931 (11)	0.64715 (19)	0.13431 (7)	0.0257 (4)
H8NA	0.0972	0.5743	0.1525	0.031*
H8NB	0.0923	0.7219	0.1503	0.031*
C8	0.04098 (11)	0.6393 (2)	0.28661 (8)	0.0175 (4)
N9	−0.02526 (10)	0.21627 (17)	0.41916 (6)	0.0189 (4)
H9NA	−0.0085	0.2124	0.3882	0.023*
C9	0.04259 (14)	0.7762 (2)	0.28768 (9)	0.0250 (5)
H9A	0.0724	0.8215	0.3138	0.030*
C10	0.0000	0.8452 (3)	0.2500	0.0301 (8)
H10A	0.0000	0.9386	0.2500	0.036*
N10	−0.03939 (10)	0.32331 (17)	0.49808 (6)	0.0179 (4)
C11	0.08390 (11)	0.5555 (2)	0.32701 (8)	0.0170 (4)
N11	−0.07504 (10)	0.09514 (17)	0.48552 (7)	0.0187 (4)
N12	0.01468 (10)	0.42995 (18)	0.43181 (7)	0.0219 (4)
H11A	0.0226	0.4986	0.4522	0.041 (8)*
H11B	0.0304	0.4273	0.4005	0.033 (7)*
C12	0.15006 (12)	0.7326 (2)	0.01068 (8)	0.0199 (4)
N13	−0.08510 (11)	0.19908 (18)	0.56239 (7)	0.0230 (4)
H13A	−0.0983	0.1240	0.5759	0.039 (8)*
H13B	−0.0842	0.2683	0.5828	0.029 (7)*
C13	0.12875 (12)	0.6464 (2)	0.08866 (8)	0.0206 (4)
N14	−0.06375 (11)	0.00349 (19)	0.40544 (7)	0.0273 (4)
H14A	−0.0459	0.0126	0.3750	0.033 (7)*
H14B	−0.0830	−0.0706	0.4158	0.036 (8)*
C14	0.19208 (12)	0.5258 (2)	0.02825 (8)	0.0217 (4)
C15	−0.01687 (11)	0.3235 (2)	0.45053 (8)	0.0171 (4)
C16	−0.06599 (12)	0.2060 (2)	0.51433 (8)	0.0183 (4)
C17	−0.05485 (11)	0.1040 (2)	0.43758 (8)	0.0188 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ca1	0.0160 (3)	0.0136 (3)	0.0145 (3)	0.000	0.0015 (2)	0.000
C1	0.0193 (11)	0.0216 (10)	0.0160 (9)	0.0004 (8)	0.0023 (8)	0.0019 (8)
N1	0.0178 (9)	0.0173 (8)	0.0150 (8)	−0.0001 (7)	0.0020 (6)	−0.0004 (6)
O1	0.0198 (8)	0.0186 (7)	0.0215 (7)	0.0008 (6)	0.0044 (6)	0.0036 (6)
O1W	0.0303 (10)	0.0852 (16)	0.0357 (10)	0.0236 (10)	−0.0111 (8)	−0.0261 (10)
O2W	0.0510 (12)	0.0472 (12)	0.0378 (10)	0.0222 (10)	−0.0160 (9)	−0.0154 (9)
O2	0.0240 (8)	0.0243 (8)	0.0200 (7)	0.0016 (6)	0.0077 (6)	0.0054 (6)
N2	0.0160 (12)	0.0156 (11)	0.0168 (11)	0.000	0.0044 (9)	0.000
C2	0.0240 (12)	0.0416 (14)	0.0227 (11)	0.0080 (11)	0.0074 (9)	0.0077 (10)
O3W	0.089 (2)	0.0615 (16)	0.0691 (17)	0.0005 (15)	−0.0175 (14)	−0.0047 (13)
N3	0.0229 (10)	0.0190 (9)	0.0250 (9)	0.0023 (7)	0.0041 (8)	0.0065 (7)
O3	0.0202 (8)	0.0223 (8)	0.0187 (7)	0.0012 (6)	0.0037 (6)	0.0027 (6)
C3	0.0242 (13)	0.0500 (16)	0.0300 (13)	0.0167 (11)	0.0075 (10)	0.0120 (11)
O4	0.0322 (9)	0.0242 (8)	0.0197 (7)	0.0030 (7)	0.0047 (6)	0.0077 (6)
C4	0.0303 (13)	0.0347 (13)	0.0227 (11)	0.0120 (11)	0.0038 (9)	0.0097 (10)
N4	0.0190 (9)	0.0227 (9)	0.0230 (9)	0.0009 (7)	0.0003 (7)	0.0035 (7)
O5	0.0249 (8)	0.0161 (7)	0.0238 (8)	−0.0007 (6)	−0.0048 (6)	−0.0004 (6)
C5	0.0209 (11)	0.0182 (10)	0.0160 (9)	0.0029 (8)	0.0022 (8)	0.0008 (7)
N5	0.0205 (9)	0.0192 (9)	0.0220 (9)	−0.0017 (7)	0.0004 (7)	0.0015 (7)
N6	0.0297 (11)	0.0248 (10)	0.0290 (10)	0.0063 (8)	0.0080 (8)	0.0063 (8)
O6	0.0250 (8)	0.0246 (8)	0.0205 (7)	−0.0011 (7)	−0.0031 (6)	−0.0052 (6)
C6	0.0188 (10)	0.0183 (10)	0.0149 (9)	−0.0030 (8)	0.0006 (8)	0.0002 (7)
N7	0.0233 (10)	0.0222 (9)	0.0217 (9)	0.0012 (8)	0.0006 (7)	0.0037 (7)
C7	0.0231 (11)	0.0117 (9)	0.0167 (9)	−0.0021 (8)	0.0029 (8)	−0.0013 (7)
N8	0.0339 (11)	0.0198 (9)	0.0241 (9)	0.0005 (8)	0.0065 (8)	0.0028 (7)
C8	0.0183 (10)	0.0171 (9)	0.0178 (9)	−0.0006 (8)	0.0055 (8)	−0.0011 (7)
N9	0.0219 (9)	0.0207 (9)	0.0147 (8)	0.0016 (7)	0.0050 (7)	0.0009 (7)
C9	0.0322 (13)	0.0194 (10)	0.0228 (11)	−0.0025 (9)	−0.0019 (9)	−0.0030 (8)
C10	0.044 (2)	0.0179 (15)	0.0273 (17)	0.000	−0.0032 (15)	0.000
N10	0.0215 (9)	0.0158 (8)	0.0167 (8)	0.0008 (7)	0.0032 (7)	0.0012 (6)
C11	0.0146 (10)	0.0199 (10)	0.0168 (9)	−0.0012 (8)	0.0034 (7)	−0.0010 (7)
N11	0.0197 (9)	0.0173 (8)	0.0193 (8)	−0.0011 (7)	0.0038 (7)	−0.0011 (7)
N12	0.0249 (10)	0.0214 (9)	0.0200 (9)	−0.0006 (8)	0.0068 (7)	0.0025 (7)
C12	0.0144 (10)	0.0228 (10)	0.0217 (10)	−0.0031 (8)	−0.0035 (8)	0.0027 (8)
N13	0.0356 (11)	0.0160 (9)	0.0182 (8)	−0.0043 (8)	0.0071 (8)	−0.0012 (7)
C13	0.0185 (10)	0.0201 (10)	0.0227 (10)	−0.0027 (8)	−0.0004 (8)	0.0012 (8)
N14	0.0353 (11)	0.0258 (10)	0.0221 (9)	−0.0079 (9)	0.0106 (8)	−0.0068 (8)
C14	0.0152 (10)	0.0234 (11)	0.0265 (11)	−0.0008 (8)	0.0009 (8)	0.0033 (8)
C15	0.0150 (10)	0.0172 (9)	0.0189 (9)	0.0024 (8)	0.0004 (7)	0.0021 (8)
C16	0.0170 (10)	0.0183 (10)	0.0197 (10)	0.0016 (8)	0.0014 (8)	0.0009 (8)
C17	0.0155 (10)	0.0206 (10)	0.0204 (10)	0.0015 (8)	0.0020 (8)	−0.0013 (8)

Geometric parameters (Å, º) top

Ca1—O1	2.5031 (14)	O5—C11	1.259 (2)
Ca1—O1ⁱ	2.5032 (14)	C5—C7	1.514 (3)
Ca1—O5ⁱ	2.5145 (15)	N5—C13	1.319 (3)
Ca1—O5	2.5145 (15)	N5—C12	1.358 (3)
Ca1—N1ⁱ	2.5184 (18)	N6—C14	1.321 (3)
Ca1—N1	2.5184 (18)	N6—H6NA	0.8800
Ca1—N2	2.542 (2)	N6—H6NB	0.8798
Ca1—O3ⁱ	2.5472 (15)	O6—C11	1.248 (2)
Ca1—O3	2.5472 (15)	N7—C12	1.329 (3)
C1—N1	1.340 (3)	N7—H7NA	0.8800
C1—C2	1.380 (3)	N7—H7NB	0.8800
C1—C6	1.511 (3)	N8—C13	1.333 (3)
N1—C5	1.337 (3)	N8—H8NA	0.8800
O1—C6	1.250 (2)	N8—H8NB	0.8800
O1W—H1WB	0.8400	C8—C9	1.393 (3)
O1W—H1WA	0.8400	C8—C11	1.514 (3)
O2W—H2WB	0.8400	N9—C15	1.362 (3)
O2W—H2WA	0.8400	N9—C17	1.361 (3)
O2—C6	1.265 (2)	N9—H9NA	0.8800
N2—C8ⁱ	1.340 (2)	C9—C10	1.384 (3)
N2—C8	1.340 (2)	C9—H9A	0.9500
C2—C3	1.385 (3)	C10—C9ⁱ	1.384 (3)
C2—H2A	0.9500	C10—H10A	0.9500
O3W—H3WB	0.8400	N10—C15	1.327 (3)
O3W—H3WA	0.8401	N10—C16	1.363 (3)
N3—C13	1.360 (3)	N11—C17	1.324 (3)
N3—C14	1.360 (3)	N11—C16	1.355 (3)
N3—H3N	0.8800	N12—C15	1.330 (3)
O3—C7	1.275 (3)	N12—H11A	0.8801
C3—C4	1.386 (3)	N12—H11B	0.8799
C3—H3A	0.9500	N13—C16	1.319 (3)
O4—C7	1.243 (2)	N13—H13A	0.8800
C4—C5	1.392 (3)	N13—H13B	0.8799
C4—H4A	0.9500	N14—C17	1.320 (3)
N4—C14	1.329 (3)	N14—H14A	0.8800
N4—C12	1.356 (3)	N14—H14B	0.8800

O1—Ca1—O1ⁱ	148.58 (7)	N1—C5—C4	122.08 (19)
O1—Ca1—O5ⁱ	75.43 (5)	N1—C5—C7	115.77 (18)
O1ⁱ—Ca1—O5ⁱ	90.55 (5)	C4—C5—C7	122.11 (19)
O1—Ca1—O5	90.55 (5)	C13—N5—C12	115.43 (19)
O1ⁱ—Ca1—O5	75.43 (5)	C14—N6—H6NA	119.0
O5ⁱ—Ca1—O5	126.94 (7)	C14—N6—H6NB	117.5
O1—Ca1—N1ⁱ	134.76 (5)	H6NA—N6—H6NB	123.4
O1ⁱ—Ca1—N1ⁱ	64.37 (5)	O1—C6—O2	125.19 (19)
O5ⁱ—Ca1—N1ⁱ	75.23 (5)	O1—C6—C1	117.84 (17)
O5—Ca1—N1ⁱ	134.68 (5)	O2—C6—C1	116.96 (18)
O1—Ca1—N1	64.37 (5)	C12—N7—H7NA	119.8
O1ⁱ—Ca1—N1	134.76 (5)	C12—N7—H7NB	121.1
O5ⁱ—Ca1—N1	134.68 (5)	H7NA—N7—H7NB	119.1
O5—Ca1—N1	75.23 (5)	O4—C7—O3	126.11 (19)
N1ⁱ—Ca1—N1	119.78 (8)	O4—C7—C5	117.75 (19)
O1—Ca1—N2	74.29 (4)	O3—C7—C5	116.14 (17)
O1ⁱ—Ca1—N2	74.29 (4)	C13—N8—H8NA	120.4
O5ⁱ—Ca1—N2	63.47 (4)	C13—N8—H8NB	120.4
O5—Ca1—N2	63.47 (4)	H8NA—N8—H8NB	117.4
N1ⁱ—Ca1—N2	120.11 (4)	N2—C8—C9	122.1 (2)
N1—Ca1—N2	120.11 (4)	N2—C8—C11	115.19 (18)
O1—Ca1—O3ⁱ	75.39 (5)	C9—C8—C11	122.70 (19)
O1ⁱ—Ca1—O3ⁱ	127.53 (5)	C15—N9—C17	119.35 (17)
O5ⁱ—Ca1—O3ⁱ	72.48 (5)	C15—N9—H9NA	123.4
O5—Ca1—O3ⁱ	152.84 (5)	C17—N9—H9NA	117.0
N1ⁱ—Ca1—O3ⁱ	63.34 (5)	C10—C9—C8	118.9 (2)
N1—Ca1—O3ⁱ	77.73 (5)	C10—C9—H9A	120.6
N2—Ca1—O3ⁱ	131.22 (3)	C8—C9—H9A	120.6
O1—Ca1—O3	127.53 (5)	C9ⁱ—C10—C9	119.1 (3)
O1ⁱ—Ca1—O3	75.39 (5)	C9ⁱ—C10—H10A	120.5
O5ⁱ—Ca1—O3	152.84 (5)	C9—C10—H10A	120.5
O5—Ca1—O3	72.48 (5)	C15—N10—C16	115.35 (18)
N1ⁱ—Ca1—O3	77.73 (5)	O6—C11—O5	125.73 (19)
N1—Ca1—O3	63.34 (5)	O6—C11—C8	117.19 (18)
N2—Ca1—O3	131.22 (3)	O5—C11—C8	117.06 (18)
O3ⁱ—Ca1—O3	97.56 (7)	C17—N11—C16	115.51 (18)
N1—C1—C2	122.86 (19)	C15—N12—H11A	118.7
N1—C1—C6	114.91 (18)	C15—N12—H11B	119.2
C2—C1—C6	122.16 (19)	H11A—N12—H11B	121.9
C5—N1—C1	118.70 (18)	N7—C12—N4	117.41 (19)
C5—N1—Ca1	121.61 (13)	N7—C12—N5	116.5 (2)
C1—N1—Ca1	119.56 (13)	N4—C12—N5	126.05 (19)
C6—O1—Ca1	120.86 (12)	C16—N13—H13A	121.4
H1WB—O1W—H1WA	104.1	C16—N13—H13B	122.1
H2WB—O2W—H2WA	109.9	H13A—N13—H13B	116.5
C8ⁱ—N2—C8	118.9 (2)	N5—C13—N8	121.3 (2)
C8ⁱ—N2—Ca1	120.53 (12)	N5—C13—N3	121.8 (2)
C8—N2—Ca1	120.53 (12)	N8—C13—N3	116.96 (19)
C3—C2—C1	118.4 (2)	C17—N14—H14A	116.7
C3—C2—H2A	120.8	C17—N14—H14B	120.1
C1—C2—H2A	120.8	H14A—N14—H14B	123.0
H3WB—O3W—H3WA	114.4	N6—C14—N4	121.3 (2)
C13—N3—C14	119.60 (18)	N6—C14—N3	117.3 (2)
C13—N3—H3N	120.4	N4—C14—N3	121.4 (2)
C14—N3—H3N	119.8	N10—C15—N12	120.64 (19)
C7—O3—Ca1	122.48 (12)	N10—C15—N9	121.73 (18)
C2—C3—C4	119.2 (2)	N12—C15—N9	117.63 (18)
C2—C3—H3A	120.4	N13—C16—N11	116.54 (19)
C4—C3—H3A	120.4	N13—C16—N10	117.51 (19)
C3—C4—C5	118.7 (2)	N11—C16—N10	125.96 (18)
C3—C4—H4A	120.7	N14—C17—N11	120.7 (2)
C5—C4—H4A	120.7	N14—C17—N9	117.33 (19)
C14—N4—C12	115.36 (18)	N11—C17—N9	121.95 (19)
C11—O5—Ca1	123.58 (13)

C2—C1—N1—C5	−0.8 (3)	N1—Ca1—O5—C11	138.44 (17)
C6—C1—N1—C5	−177.72 (18)	N2—Ca1—O5—C11	3.08 (14)
C2—C1—N1—Ca1	175.25 (18)	O3ⁱ—Ca1—O5—C11	132.90 (16)
C6—C1—N1—Ca1	−1.6 (2)	O3—Ca1—O5—C11	−155.35 (17)
O1—Ca1—N1—C5	171.11 (17)	C1—N1—C5—C4	0.2 (3)
O1ⁱ—Ca1—N1—C5	22.09 (19)	Ca1—N1—C5—C4	−175.81 (17)
O5ⁱ—Ca1—N1—C5	−158.97 (14)	C1—N1—C5—C7	177.82 (18)
O5—Ca1—N1—C5	73.20 (15)	Ca1—N1—C5—C7	1.8 (2)
N1ⁱ—Ca1—N1—C5	−60.19 (14)	C3—C4—C5—N1	0.4 (4)
N2—Ca1—N1—C5	119.81 (14)	C3—C4—C5—C7	−177.1 (2)
O3ⁱ—Ca1—N1—C5	−109.38 (16)	Ca1—O1—C6—O2	162.52 (16)
O3—Ca1—N1—C5	−4.32 (14)	Ca1—O1—C6—C1	−19.1 (2)
O1—Ca1—N1—C1	−4.88 (14)	N1—C1—C6—O1	13.5 (3)
O1ⁱ—Ca1—N1—C1	−153.89 (14)	C2—C1—C6—O1	−163.4 (2)
O5ⁱ—Ca1—N1—C1	25.05 (18)	N1—C1—C6—O2	−167.97 (18)
O5—Ca1—N1—C1	−102.78 (15)	C2—C1—C6—O2	15.1 (3)
N1ⁱ—Ca1—N1—C1	123.83 (16)	Ca1—O3—C7—O4	170.52 (16)
N2—Ca1—N1—C1	−56.17 (16)	Ca1—O3—C7—C5	−9.4 (2)
O3ⁱ—Ca1—N1—C1	74.64 (15)	N1—C5—C7—O4	−175.02 (18)
O3—Ca1—N1—C1	179.70 (17)	C4—C5—C7—O4	2.6 (3)
O1ⁱ—Ca1—O1—C6	148.51 (15)	N1—C5—C7—O3	4.9 (3)
O5ⁱ—Ca1—O1—C6	−145.46 (15)	C4—C5—C7—O3	−177.5 (2)
O5—Ca1—O1—C6	86.33 (15)	C8ⁱ—N2—C8—C9	−0.29 (15)
N1ⁱ—Ca1—O1—C6	−94.42 (16)	Ca1—N2—C8—C9	179.71 (15)
N1—Ca1—O1—C6	13.04 (14)	C8ⁱ—N2—C8—C11	178.57 (19)
N2—Ca1—O1—C6	148.51 (15)	Ca1—N2—C8—C11	−1.43 (19)
O3ⁱ—Ca1—O1—C6	−70.16 (15)	N2—C8—C9—C10	0.6 (3)
O3—Ca1—O1—C6	18.19 (17)	C11—C8—C9—C10	−178.21 (17)
O1—Ca1—N2—C8ⁱ	80.76 (10)	C8—C9—C10—C9ⁱ	−0.27 (14)
O1ⁱ—Ca1—N2—C8ⁱ	−99.24 (10)	Ca1—O5—C11—O6	173.48 (15)
O5ⁱ—Ca1—N2—C8ⁱ	−0.53 (11)	Ca1—O5—C11—C8	−5.0 (2)
O5—Ca1—N2—C8ⁱ	179.47 (11)	N2—C8—C11—O6	−174.49 (16)
N1ⁱ—Ca1—N2—C8ⁱ	−52.29 (11)	C9—C8—C11—O6	4.4 (3)
N1—Ca1—N2—C8ⁱ	127.71 (11)	N2—C8—C11—O5	4.1 (3)
O3ⁱ—Ca1—N2—C8ⁱ	27.26 (11)	C9—C8—C11—O5	−177.1 (2)
O3—Ca1—N2—C8ⁱ	−152.74 (11)	C14—N4—C12—N7	−177.40 (19)
O1—Ca1—N2—C8	−99.24 (10)	C14—N4—C12—N5	1.4 (3)
O1ⁱ—Ca1—N2—C8	80.76 (10)	C13—N5—C12—N7	172.95 (19)
O5ⁱ—Ca1—N2—C8	179.47 (11)	C13—N5—C12—N4	−5.9 (3)
O5—Ca1—N2—C8	−0.53 (11)	C12—N5—C13—N8	−173.9 (2)
N1ⁱ—Ca1—N2—C8	127.71 (11)	C12—N5—C13—N3	4.3 (3)
N1—Ca1—N2—C8	−52.29 (11)	C14—N3—C13—N5	1.3 (3)
O3ⁱ—Ca1—N2—C8	−152.74 (11)	C14—N3—C13—N8	179.6 (2)
O3—Ca1—N2—C8	27.26 (11)	C12—N4—C14—N6	−174.6 (2)
N1—C1—C2—C3	0.8 (4)	C12—N4—C14—N3	4.7 (3)
C6—C1—C2—C3	177.5 (2)	C13—N3—C14—N6	173.2 (2)
O1—Ca1—O3—C7	2.23 (17)	C13—N3—C14—N4	−6.2 (3)
O1ⁱ—Ca1—O3—C7	−153.52 (15)	C16—N10—C15—N12	−175.54 (19)
O5ⁱ—Ca1—O3—C7	145.59 (14)	C16—N10—C15—N9	4.7 (3)
O5—Ca1—O3—C7	−74.48 (15)	C17—N9—C15—N10	−2.6 (3)
N1ⁱ—Ca1—O3—C7	140.11 (15)	C17—N9—C15—N12	177.67 (18)
N1—Ca1—O3—C7	7.43 (14)	C17—N11—C16—N13	−179.39 (19)
N2—Ca1—O3—C7	−100.42 (14)	C17—N11—C16—N10	0.9 (3)
O3ⁱ—Ca1—O3—C7	79.58 (14)	C15—N10—C16—N13	176.27 (19)
C1—C2—C3—C4	−0.2 (4)	C15—N10—C16—N11	−4.0 (3)
C2—C3—C4—C5	−0.4 (4)	C16—N11—C17—N14	−177.5 (2)
O1—Ca1—O5—C11	75.17 (16)	C16—N11—C17—N9	1.6 (3)
O1ⁱ—Ca1—O5—C11	−76.38 (16)	C15—N9—C17—N14	178.31 (19)
O5ⁱ—Ca1—O5—C11	3.08 (14)	C15—N9—C17—N11	−0.8 (3)
N1ⁱ—Ca1—O5—C11	−104.08 (16)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WB···O2ⁱⁱ	0.84	1.91	2.710 (3)	160
O1W—H1WA···O6ⁱⁱⁱ	0.84	1.92	2.751 (3)	170
O2W—H2WB···N4^iv	0.84	2.26	3.022 (3)	151
N3—H3N···O2	0.88	1.79	2.667 (2)	176
O2W—H2WA···O5	0.84	2.05	2.888 (3)	175
O3W—H3WB···O2W^v	0.84	2.18	2.963 (3)	154
O3W—H3WA···N14^vi	0.84	2.17	3.007 (3)	180
N6—H6NA···O1Wⁱⁱ	0.88	2.45	3.294 (3)	162
N6—H6NB···O1W	0.88	1.90	2.740 (3)	160
N7—H7NA···N11^vi	0.88	2.22	3.103 (3)	176
N7—H7NB···O2Wⁱⁱⁱ	0.88	2.44	3.205 (3)	146
N7—H7NB···O4ⁱⁱⁱ	0.88	2.53	3.111 (2)	124
N8—H8NA···O1	0.88	2.07	2.948 (2)	172
N12—H11A···N10^vii	0.88	2.23	3.109 (2)	178
N12—H11B···O5	0.88	2.32	3.196 (2)	175
N8—H8NB···O3W	0.88	2.15	2.832 (4)	134
N9—H9NA···O3	0.88	1.89	2.754 (2)	165
N13—H13A···O4^viii	0.88	2.08	2.925 (2)	160
N13—H13B···O6^vii	0.88	1.96	2.790 (2)	157
N14—H14A···O3	0.88	2.39	3.143 (2)	144
N14—H14B···N5^ix	0.88	2.10	2.978 (3)	178
C4—H4A···O2^x	0.95	2.55	3.370 (3)	145

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

Experimental details

Crystal data
Chemical formula	(C₃H₇N₆)₄[Ca(C₇H₃NO₄)₃]·6H₂O
M_r	1152.07
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	17.9605 (15), 10.1672 (9), 25.922 (2)
β (°)	94.467 (2)
V (Å³)	4719.1 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.928, 0.954
No. of measured, independent and observed [I > 2σ(I)] reflections	16983, 6215, 4412
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.682

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.127, 1.09
No. of reflections	6215
No. of parameters	365
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.51, −0.77

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1W—H1WB···O2ⁱ	0.84	1.91	2.710 (3)	160
O1W—H1WA···O6ⁱⁱ	0.84	1.92	2.751 (3)	170
O2W—H2WB···N4ⁱⁱⁱ	0.84	2.26	3.022 (3)	151
N3—H3N···O2	0.88	1.79	2.667 (2)	176
O2W—H2WA···O5	0.84	2.05	2.888 (3)	175
O3W—H3WB···O2W^iv	0.84	2.18	2.963 (3)	154
O3W—H3WA···N14^v	0.84	2.17	3.007 (3)	180
N6—H6NA···O1Wⁱ	0.88	2.45	3.294 (3)	162
N6—H6NB···O1W	0.88	1.90	2.740 (3)	160
N7—H7NA···N11^v	0.88	2.22	3.103 (3)	176
N7—H7NB···O2Wⁱⁱ	0.88	2.44	3.205 (3)	146
N7—H7NB···O4ⁱⁱ	0.88	2.53	3.111 (2)	124
N8—H8NA···O1	0.88	2.07	2.948 (2)	172
N12—H11A···N10^vi	0.88	2.23	3.109 (2)	178
N12—H11B···O5	0.88	2.32	3.196 (2)	175
N8—H8NB···O3W	0.88	2.15	2.832 (4)	134
N9—H9NA···O3	0.88	1.89	2.754 (2)	165
N13—H13A···O4^vii	0.88	2.08	2.925 (2)	160
N13—H13B···O6^vi	0.88	1.96	2.790 (2)	157
N14—H14A···O3	0.88	2.39	3.143 (2)	144
N14—H14B···N5^viii	0.88	2.10	2.978 (3)	178
C4—H4A···O2^ix	0.95	2.55	3.370 (3)	145

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

References

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Volume 64| Part 8| August 2008| Pages m1063-m1064

doi:10.1107/S1600536808022873

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

Tetra­kis(2,4,6-tri­amino-1,3,5-triazin-1-ium) tris­­(pyridine-2,6-di­carboxyl­ato)calcate(II) hexa­hydrate

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metal-organic compounds

Tetrakis(2,4,6-triamino-1,3,5-triazin-1-ium) tris(pyridine-2,6-dicarboxylato)calcate(II) hexahydrate