Propane-1,2-diaminium bis­(pyridine-2,6-dicarboxyl­ato-κ3O2,N,O6)cadmate dihydrate

Aghabozorg, H.; Khazaie, Z.; Agah, A.A.; Saemi, M.; Notash, B.

doi:10.1107/S160053681102438X

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page m982

doi:10.1107/S160053681102438X

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Propane-1,2-diaminium bis(pyridine-2,6-dicarboxylato-κ³O²,N,O⁶)cadmate dihydrate

Hossein Aghabozorg,^a Zeynab Khazaie,^a Ali Akbar Agah,^a ^* Maryam Saemi ^a and Behrouz Notash ^b

^aFaculty of Chemistry, Tarbiat Moallem University, 15614, Tehran, Iran, and ^bDepartment of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran, 1983963113, Iran
^*Correspondence e-mail: agah2006@yahoo.com

(Received 9 May 2011; accepted 21 June 2011; online 25 June 2011)

The reaction of cadmium nitrate dihydrate, propane-1,2-diamine and pyridine-2,6-dicarboxylic acid in a 1:1:2 molar ratio in an aqueous solution resulted in the formation of the title compound, (C₃H₁₂N₂)[Cd(C₇H₃NO₄)₂]·2H₂O or (p-1,2-daH₂)-[Cd(pydc)₂]·2H₂O (where p-1,2-da is propane-1,2-diamine and pydcH₂ is pyridine-2,6-dicarboxylic acid). The Cd^II ion is coordinated by four O and two N atoms of two pydc ligands in a distorted octahedral environment. The structure also contains two uncoordinated water molecules. In the crystal, there are several intermolecular N—H⋯O, O—H⋯O and weak C—H⋯O hydrogen bonds. There are also π–π stacking interactions between the pyridine rings of pydc units, with centroid–centroid distances of 3.4708 (16) Å.

Related literature

For related proton-transfer compounds reported by our group, see: Aghabozorg et al. (2008a ,b ,c ,d ); Pasdar et al. (2011 ).

Experimental

Crystal data

(C₃H₁₂N₂)[Cd(C₇H₃NO₄)₂]·2H₂O
M_r = 554.80
Triclinic, $[P \overline 1]$
a = 8.6227 (17) Å
b = 10.133 (2) Å
c = 13.448 (3) Å
α = 81.36 (3)°
β = 76.73 (3)°
γ = 65.38 (3)°
V = 1037.7 (5) Å³
Z = 2
Mo Kα radiation
μ = 1.12 mm⁻¹
T = 298 K
0.30 × 0.20 × 0.15 mm

Data collection

Stoe IPDS 2T diffractometer
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005 )T_min = 0.764, T_max = 0.842
11690 measured reflections
5554 independent reflections
4562 reflections with I > 2σ(I)
R_int = 0.035

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.063
S = 1.02
5554 reflections
330 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.50 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O10ⁱ	0.89 (3)	1.90 (3)	2.780 (3)	172 (3)
N3—H3B⋯O3ⁱⁱ	0.86 (3)	2.04 (3)	2.899 (3)	177 (3)
N3—H3C⋯O2ⁱ	0.92 (2)	1.89 (2)	2.790 (3)	164 (3)
N4—H4A⋯O8ⁱⁱ	0.91 (3)	1.96 (3)	2.870 (3)	176 (3)
N4—H4B⋯O5	0.83 (3)	2.06 (3)	2.889 (3)	172 (3)
N4—H4C⋯O9ⁱⁱ	0.91 (3)	1.90 (3)	2.803 (3)	170 (3)
O9—H9A⋯O4ⁱⁱⁱ	0.76 (4)	1.96 (4)	2.708 (3)	170 (4)
O9—H9B⋯O2^iv	0.84 (4)	2.00 (4)	2.827 (3)	165 (4)
O10—H10A⋯O6^v	0.88 (6)	2.04 (6)	2.848 (4)	151 (6)
O10—H10B⋯O8^vi	0.74 (4)	2.19 (4)	2.835 (3)	147 (4)
C10—H10⋯O3^vii	0.93	2.54	3.298 (3)	139
C12—H12⋯O1^vi	0.93	2.44	3.200 (3)	139
Symmetry codes: (i) x+1, y, z; (ii) x, y+1, z; (iii) x-1, y, z; (iv) x, y-1, z; (v) -x+1, -y+2, -z+1; (vi) -x+1, -y+1, -z+1; (vii) -x+2, -y+1, -z+1.

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

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681102438X/bt5545sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681102438X/bt5545Isup2.hkl

checkCIF report

Comment top

Our group has previously reported some proton transfer systems, using pyridine-2,6-dicarboxylic acid(pydcH₂), propane-1,2-diamine(p-1,2-da) and propane-1,3-diamine (p-1,3-da) which formed the proton transfer compounds (pnH₂)(pydcH)₂.2H₂O(Aghabozorg, et al., 2008d), (p-1,3daH₂)[Cd(pydc)₂]. 3.5H₂O (Aghabozorg, et al., 2008b), (C₃H₁₂N₂)[Ni(C₇H₃NO₄)₂].4H₂O (Hossein Aghabozorg et al., 2008c), (pnH₂)[Hg(hypydc)Cl(H₂O)]₂.4H₂O (Aghabozorg, et al., 2008a) and (p-1,2-daH₂)[Zr(pydc)₃].3H₂O(Pasdar, et al., 2011).

The crystal structure of the title compound is shown in Fig. 1. The Cd(II) ion is six coordinated by two (pydc)^2- groups in a distorted octahedral environment. The torsion angles O(5)—Cd(1)—O(3)—C(7) and O(3)—Cd(1)—O(5)—C(8) are 67.86 (15)° and 108.19 (17)° respectively, and also the angles O(7)—Cd(1)—O(1) and O(3)—Cd(1)—O(5) are 103.92 (7)° and 105.44 (6)° respectively, indicate that the two (pydc)^2- units are not perpendicular to one another. In the crystal structure of the title compound, there are several intermolecular N—H···O, O—H···O and weak C—H···O hydrogen bonding (Table 1 & Fig. 2). There are also π–π stacking interactions between the pyridine rings of pydc moieties with a centroid to centroid distance of 3.4708 (16) Å (Fig. 3).

Related literature top

For related proton-transfer compounds reported by our group, see: Aghabozorg et al. (2008a,b,c,d); Pasdar et al. (2011).

Experimental top

An aqueous solution (30 ml) of propane-1,2-diamine(1 mmol), pyridine-2,6-dicarboxylic acid (2 mmol) and cadmium(II) nitrate dihydrate(1 mmol) were stirred at room temperature. Colorless crystals of the title compound were obtained after three weeks at room temperature.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at 30% probability level.
	Fig. 2. The packing diagram of the title compound viewed down the a-axis. The intermolecular N—H···O, O—H···O and weak C—H···O hydrogen bonds are shown as blue dashed lines.
	Fig. 3. The packing diagram of the title compound showing π-π interactions between pydc fragments.Only anionic parts are shown for clarity.

Propane-1,2-diaminium bis(pyridine-2,6-dicarboxylato- κ³O²,N,O⁶)cadmate dihydrate top

Crystal data top

(C₃H₁₂N₂)[Cd(C₇H₃NO₄)₂]·2H₂O	Z = 2
M_r = 554.80	F(000) = 560
Triclinic, P1	D_x = 1.776 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6227 (17) Å	Cell parameters from 5554 reflections
b = 10.133 (2) Å	θ = 2.2–29.2°
c = 13.448 (3) Å	µ = 1.12 mm⁻¹
α = 81.36 (3)°	T = 298 K
β = 76.73 (3)°	Plate, colorless
γ = 65.38 (3)°	0.3 × 0.2 × 0.15 mm
V = 1037.7 (5) Å³

Data collection top

Stoe IPDS 2T diffractometer	5554 independent reflections
Radiation source: fine-focus sealed tube	4562 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.035
Detector resolution: 0.15 mm pixels mm^-1	θ_max = 29.2°, θ_min = 2.2°
rotation method scans	h = −10→11
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005)	k = −13→13
T_min = 0.764, T_max = 0.842	l = −18→18
11690 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.063	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.030P)² + 0.1592P] where P = (F_o² + 2F_c²)/3
5554 reflections	(Δ/σ)_max = 0.002
330 parameters	Δρ_max = 0.50 e Å⁻³
1 restraint	Δρ_min = −0.37 e Å⁻³

Crystal data top

(C₃H₁₂N₂)[Cd(C₇H₃NO₄)₂]·2H₂O	γ = 65.38 (3)°
M_r = 554.80	V = 1037.7 (5) Å³
Triclinic, P1	Z = 2
a = 8.6227 (17) Å	Mo Kα radiation
b = 10.133 (2) Å	µ = 1.12 mm⁻¹
c = 13.448 (3) Å	T = 298 K
α = 81.36 (3)°	0.3 × 0.2 × 0.15 mm
β = 76.73 (3)°

Data collection top

Stoe IPDS 2T diffractometer	5554 independent reflections
Absorption correction: numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005)	4562 reflections with I > 2σ(I)
T_min = 0.764, T_max = 0.842	R_int = 0.035
11690 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	1 restraint
wR(F²) = 0.063	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	Δρ_max = 0.50 e Å⁻³
5554 reflections	Δρ_min = −0.37 e Å⁻³
330 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
N3	1.0640 (3)	1.0203 (2)	0.73941 (18)	0.0427 (4)
Cd1	0.66437 (2)	0.504594 (16)	0.721726 (12)	0.03837 (6)
O2	0.2288 (2)	0.84128 (17)	0.89531 (14)	0.0470 (4)
O1	0.3826 (2)	0.68084 (17)	0.77635 (13)	0.0459 (4)
C2	0.5023 (3)	0.66583 (19)	0.92189 (15)	0.0292 (4)
N1	0.6429 (2)	0.55580 (16)	0.88029 (12)	0.0291 (3)
C6	0.7749 (3)	0.4828 (2)	0.92965 (15)	0.0296 (4)
O5	0.7653 (2)	0.69575 (17)	0.65361 (13)	0.0472 (4)
C1	0.3595 (3)	0.7347 (2)	0.85908 (16)	0.0345 (4)
O3	0.8962 (2)	0.31965 (15)	0.79612 (12)	0.0404 (3)
O7	0.6154 (2)	0.31945 (16)	0.67431 (12)	0.0443 (4)
N2	0.7307 (2)	0.50583 (17)	0.55184 (12)	0.0318 (3)
O4	1.0562 (2)	0.29857 (19)	0.91131 (16)	0.0581 (5)
O6	0.8533 (3)	0.80395 (19)	0.50805 (16)	0.0598 (5)
C5	0.7702 (3)	0.5199 (2)	1.02547 (16)	0.0363 (4)
H5	0.8626	0.4691	1.0595	0.044*
C9	0.7864 (3)	0.6038 (2)	0.49661 (16)	0.0352 (4)
C4	0.6252 (3)	0.6340 (2)	1.06974 (16)	0.0385 (5)
H4	0.6193	0.6606	1.1342	0.046*
C3	0.4892 (3)	0.7083 (2)	1.01798 (16)	0.0355 (4)
H3	0.3909	0.7851	1.0469	0.043*
C7	0.9229 (3)	0.3556 (2)	0.87480 (16)	0.0340 (4)
C14	0.6464 (3)	0.3028 (2)	0.58002 (17)	0.0382 (5)
C13	0.7083 (3)	0.4078 (2)	0.50696 (16)	0.0330 (4)
C8	0.8043 (3)	0.7107 (2)	0.55696 (19)	0.0408 (5)
O8	0.6343 (3)	0.20351 (18)	0.54186 (14)	0.0550 (5)
N4	0.6575 (3)	0.9894 (2)	0.71014 (17)	0.0395 (4)
C16	0.7838 (3)	0.9958 (2)	0.76668 (16)	0.0362 (4)
H16	0.7338	1.0911	0.7957	0.043*
C12	0.7429 (3)	0.4046 (3)	0.40160 (17)	0.0416 (5)
H12	0.7277	0.3358	0.3706	0.050*
C15	0.9497 (3)	0.9831 (2)	0.69164 (18)	0.0410 (5)
H15A	1.0104	0.8845	0.6697	0.049*
H15B	0.9212	1.0482	0.6317	0.049*
C11	0.8002 (3)	0.5050 (3)	0.34338 (18)	0.0505 (6)
H11	0.8236	0.5048	0.2724	0.061*
C10	0.8232 (3)	0.6062 (3)	0.39052 (18)	0.0450 (5)
H10	0.8623	0.6743	0.3520	0.054*
C17	0.8098 (4)	0.8803 (3)	0.8543 (2)	0.0649 (8)
H17A	0.7007	0.8971	0.8997	0.097*
H17B	0.8906	0.8847	0.8910	0.097*
H17C	0.8545	0.7861	0.8277	0.097*
O9	0.3551 (3)	0.0640 (3)	0.8606 (2)	0.0659 (6)
O10	0.3774 (3)	0.9659 (3)	0.60376 (17)	0.0623 (5)
H4C	0.553 (4)	1.013 (3)	0.754 (2)	0.050 (8)*
H4B	0.696 (4)	0.906 (3)	0.690 (2)	0.057 (8)*
H4A	0.651 (4)	1.054 (3)	0.655 (2)	0.059 (8)*
H9A	0.276 (6)	0.135 (5)	0.869 (3)	0.090 (13)*
H10B	0.404 (5)	0.899 (4)	0.577 (3)	0.076 (13)*
H10A	0.341 (8)	1.039 (7)	0.558 (5)	0.16 (2)*
H9B	0.317 (5)	−0.001 (4)	0.883 (3)	0.081 (12)*
H3C	1.100 (4)	0.957 (3)	0.7943 (18)	0.061 (9)*
H3A	1.159 (4)	1.011 (3)	0.693 (2)	0.057 (8)*
H3B	1.013 (4)	1.108 (4)	0.758 (2)	0.061 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N3	0.0314 (10)	0.0350 (10)	0.0587 (13)	−0.0071 (8)	−0.0084 (10)	−0.0124 (9)
Cd1	0.05293 (11)	0.03011 (8)	0.02906 (8)	−0.01047 (6)	−0.01066 (6)	−0.00649 (5)
O2	0.0355 (9)	0.0356 (8)	0.0624 (11)	−0.0006 (7)	−0.0148 (8)	−0.0127 (7)
O1	0.0479 (9)	0.0413 (8)	0.0447 (9)	−0.0050 (7)	−0.0223 (7)	−0.0084 (7)
C2	0.0304 (10)	0.0243 (8)	0.0341 (9)	−0.0113 (7)	−0.0054 (8)	−0.0048 (7)
N1	0.0313 (9)	0.0251 (7)	0.0312 (8)	−0.0094 (6)	−0.0077 (7)	−0.0048 (6)
C6	0.0282 (10)	0.0279 (8)	0.0342 (9)	−0.0127 (7)	−0.0053 (8)	−0.0022 (7)
O5	0.0632 (11)	0.0349 (8)	0.0474 (9)	−0.0195 (7)	−0.0135 (8)	−0.0092 (7)
C1	0.0345 (11)	0.0270 (9)	0.0423 (11)	−0.0099 (8)	−0.0119 (9)	−0.0027 (8)
O3	0.0421 (9)	0.0311 (7)	0.0386 (8)	−0.0030 (6)	−0.0073 (7)	−0.0093 (6)
O7	0.0632 (11)	0.0335 (7)	0.0388 (8)	−0.0203 (7)	−0.0113 (8)	−0.0035 (6)
N2	0.0331 (9)	0.0270 (7)	0.0313 (8)	−0.0056 (7)	−0.0093 (7)	−0.0040 (6)
O4	0.0351 (9)	0.0504 (10)	0.0833 (14)	0.0012 (8)	−0.0240 (9)	−0.0222 (9)
O6	0.0699 (13)	0.0428 (9)	0.0738 (13)	−0.0306 (9)	−0.0176 (11)	0.0068 (9)
C5	0.0360 (11)	0.0402 (10)	0.0379 (11)	−0.0172 (9)	−0.0134 (9)	−0.0018 (8)
C9	0.0294 (10)	0.0316 (9)	0.0384 (10)	−0.0051 (8)	−0.0084 (8)	−0.0022 (8)
C4	0.0453 (13)	0.0426 (11)	0.0329 (10)	−0.0197 (10)	−0.0074 (9)	−0.0111 (8)
C3	0.0352 (11)	0.0335 (9)	0.0371 (10)	−0.0121 (8)	−0.0028 (9)	−0.0108 (8)
C7	0.0301 (10)	0.0257 (9)	0.0429 (11)	−0.0085 (8)	−0.0045 (9)	−0.0036 (8)
C14	0.0404 (12)	0.0270 (9)	0.0453 (12)	−0.0053 (8)	−0.0168 (10)	−0.0070 (8)
C13	0.0308 (10)	0.0286 (9)	0.0352 (10)	−0.0026 (8)	−0.0111 (8)	−0.0089 (7)
C8	0.0362 (12)	0.0285 (9)	0.0538 (13)	−0.0067 (8)	−0.0123 (10)	−0.0037 (9)
O8	0.0795 (13)	0.0384 (8)	0.0578 (10)	−0.0255 (9)	−0.0245 (10)	−0.0093 (7)
N4	0.0381 (11)	0.0341 (10)	0.0483 (11)	−0.0121 (8)	−0.0127 (9)	−0.0080 (8)
C16	0.0352 (11)	0.0325 (10)	0.0414 (11)	−0.0106 (8)	−0.0103 (9)	−0.0072 (8)
C12	0.0379 (12)	0.0452 (12)	0.0369 (11)	−0.0055 (9)	−0.0115 (9)	−0.0147 (9)
C15	0.0353 (12)	0.0378 (11)	0.0477 (12)	−0.0093 (9)	−0.0085 (10)	−0.0110 (9)
C11	0.0472 (14)	0.0666 (16)	0.0287 (10)	−0.0145 (12)	−0.0042 (10)	−0.0058 (10)
C10	0.0390 (12)	0.0520 (13)	0.0385 (11)	−0.0160 (10)	−0.0037 (10)	0.0018 (10)
C17	0.0664 (19)	0.0728 (19)	0.0647 (18)	−0.0363 (16)	−0.0286 (15)	0.0201 (15)
O9	0.0449 (11)	0.0434 (10)	0.0973 (17)	−0.0131 (9)	0.0117 (11)	−0.0213 (11)
O10	0.0782 (15)	0.0666 (14)	0.0503 (11)	−0.0389 (12)	−0.0044 (10)	−0.0085 (11)

Geometric parameters (Å, º) top

N3—C15	1.483 (3)	C9—C8	1.522 (3)
N3—H3C	0.924 (18)	C4—C3	1.381 (3)
N3—H3A	0.89 (3)	C4—H4	0.9300
N3—H3B	0.86 (3)	C3—H3	0.9300
Cd1—N1	2.2185 (16)	C14—O8	1.246 (3)
Cd1—N2	2.2236 (17)	C14—C13	1.517 (3)
Cd1—O7	2.2906 (16)	C13—C12	1.382 (3)
Cd1—O1	2.364 (2)	N4—C16	1.490 (3)
Cd1—O3	2.3965 (18)	N4—H4C	0.91 (3)
Cd1—O5	2.4197 (18)	N4—H4B	0.83 (3)
O2—C1	1.252 (3)	N4—H4A	0.91 (3)
O1—C1	1.251 (3)	C16—C17	1.515 (3)
C2—N1	1.333 (3)	C16—C15	1.518 (3)
C2—C3	1.388 (3)	C16—H16	0.9800
C2—C1	1.517 (3)	C12—C11	1.376 (4)
N1—C6	1.334 (3)	C12—H12	0.9300
C6—C5	1.383 (3)	C15—H15A	0.9700
C6—C7	1.522 (3)	C15—H15B	0.9700
O5—C8	1.268 (3)	C11—C10	1.384 (4)
O3—C7	1.266 (3)	C11—H11	0.9300
O7—C14	1.257 (3)	C10—H10	0.9300
N2—C9	1.334 (3)	C17—H17A	0.9600
N2—C13	1.335 (3)	C17—H17B	0.9600
O4—C7	1.231 (3)	C17—H17C	0.9600
O6—C8	1.234 (3)	O9—H9A	0.76 (4)
C5—C4	1.384 (3)	O9—H9B	0.84 (4)
C5—H5	0.9300	O10—H10B	0.74 (4)
C9—C10	1.387 (3)	O10—H10A	0.88 (6)

C15—N3—H3C	112.1 (19)	C4—C3—H3	120.7
C15—N3—H3A	107.1 (19)	C2—C3—H3	120.7
H3C—N3—H3A	107 (3)	O4—C7—O3	126.7 (2)
C15—N3—H3B	111 (2)	O4—C7—C6	116.74 (19)
H3C—N3—H3B	110 (3)	O3—C7—C6	116.52 (18)
H3A—N3—H3B	110 (3)	O8—C14—O7	124.7 (2)
N1—Cd1—N2	160.33 (6)	O8—C14—C13	117.2 (2)
N1—Cd1—O7	126.63 (6)	O7—C14—C13	118.04 (18)
N2—Cd1—O7	72.61 (6)	N2—C13—C12	120.8 (2)
N1—Cd1—O1	71.23 (7)	N2—C13—C14	114.95 (17)
N2—Cd1—O1	110.88 (7)	C12—C13—C14	124.22 (19)
O7—Cd1—O1	103.92 (7)	O6—C8—O5	126.1 (2)
N1—Cd1—O3	70.42 (6)	O6—C8—C9	117.6 (2)
N2—Cd1—O3	110.59 (7)	O5—C8—C9	116.27 (19)
O7—Cd1—O3	86.77 (6)	C16—N4—H4C	107.8 (18)
O1—Cd1—O3	138.50 (6)	C16—N4—H4B	108 (2)
N1—Cd1—O5	90.60 (6)	H4C—N4—H4B	113 (3)
N2—Cd1—O5	70.02 (6)	C16—N4—H4A	108.2 (19)
O7—Cd1—O5	142.62 (6)	H4C—N4—H4A	111 (3)
O1—Cd1—O5	90.16 (7)	H4B—N4—H4A	109 (3)
O3—Cd1—O5	105.44 (6)	N4—C16—C17	109.4 (2)
C1—O1—Cd1	115.64 (14)	N4—C16—C15	108.95 (18)
N1—C2—C3	120.81 (19)	C17—C16—C15	114.1 (2)
N1—C2—C1	115.44 (17)	N4—C16—H16	108.1
C3—C2—C1	123.71 (18)	C17—C16—H16	108.1
C2—N1—C6	121.19 (17)	C15—C16—H16	108.1
C2—N1—Cd1	118.94 (13)	C11—C12—C13	118.8 (2)
C6—N1—Cd1	119.73 (13)	C11—C12—H12	120.6
N1—C6—C5	120.86 (19)	C13—C12—H12	120.6
N1—C6—C7	115.26 (17)	N3—C15—C16	110.77 (19)
C5—C6—C7	123.83 (19)	N3—C15—H15A	109.5
C8—O5—Cd1	116.58 (14)	C16—C15—H15A	109.5
O1—C1—O2	126.0 (2)	N3—C15—H15B	109.5
O1—C1—C2	117.64 (18)	C16—C15—H15B	109.5
O2—C1—C2	116.35 (18)	H15A—C15—H15B	108.1
C7—O3—Cd1	114.43 (12)	C12—C11—C10	120.0 (2)
C14—O7—Cd1	116.65 (14)	C12—C11—H11	120.0
C9—N2—C13	121.17 (18)	C10—C11—H11	120.0
C9—N2—Cd1	121.10 (14)	C11—C10—C9	118.5 (2)
C13—N2—Cd1	117.70 (14)	C11—C10—H10	120.8
C6—C5—C4	118.7 (2)	C9—C10—H10	120.8
C6—C5—H5	120.6	C16—C17—H17A	109.5
C4—C5—H5	120.6	C16—C17—H17B	109.5
N2—C9—C10	120.7 (2)	H17A—C17—H17B	109.5
N2—C9—C8	116.00 (18)	C16—C17—H17C	109.5
C10—C9—C8	123.3 (2)	H17A—C17—H17C	109.5
C3—C4—C5	119.84 (19)	H17B—C17—H17C	109.5
C3—C4—H4	120.1	H9A—O9—H9B	104 (4)
C5—C4—H4	120.1	H10B—O10—H10A	106 (4)
C4—C3—C2	118.59 (19)

N1—Cd1—O1—C1	9.37 (15)	O3—Cd1—N2—C9	−100.88 (15)
N2—Cd1—O1—C1	−149.82 (15)	O5—Cd1—N2—C9	−1.33 (15)
O7—Cd1—O1—C1	133.77 (16)	N1—Cd1—N2—C13	170.20 (16)
O3—Cd1—O1—C1	32.7 (2)	O7—Cd1—N2—C13	1.35 (14)
O5—Cd1—O1—C1	−81.21 (16)	O1—Cd1—N2—C13	−97.29 (15)
C3—C2—N1—C6	0.3 (3)	O3—Cd1—N2—C13	80.95 (15)
C1—C2—N1—C6	−177.55 (17)	O5—Cd1—N2—C13	−179.50 (16)
C3—C2—N1—Cd1	−175.32 (14)	N1—C6—C5—C4	0.3 (3)
C1—C2—N1—Cd1	6.9 (2)	C7—C6—C5—C4	−177.21 (19)
N2—Cd1—N1—C2	91.3 (2)	C13—N2—C9—C10	−0.2 (3)
O7—Cd1—N1—C2	−101.95 (15)	Cd1—N2—C9—C10	−178.30 (16)
O1—Cd1—N1—C2	−8.29 (14)	C13—N2—C9—C8	179.24 (18)
O3—Cd1—N1—C2	−172.14 (16)	Cd1—N2—C9—C8	1.1 (2)
O5—Cd1—N1—C2	81.67 (15)	C6—C5—C4—C3	−0.1 (3)
N2—Cd1—N1—C6	−84.3 (2)	C5—C4—C3—C2	−0.1 (3)
O7—Cd1—N1—C6	82.38 (16)	N1—C2—C3—C4	0.0 (3)
O1—Cd1—N1—C6	176.04 (16)	C1—C2—C3—C4	177.62 (19)
O3—Cd1—N1—C6	12.20 (13)	Cd1—O3—C7—O4	−160.3 (2)
O5—Cd1—N1—C6	−93.99 (15)	Cd1—O3—C7—C6	19.5 (2)
C2—N1—C6—C5	−0.4 (3)	N1—C6—C7—O4	170.5 (2)
Cd1—N1—C6—C5	175.12 (15)	C5—C6—C7—O4	−11.9 (3)
C2—N1—C6—C7	177.30 (17)	N1—C6—C7—O3	−9.4 (3)
Cd1—N1—C6—C7	−7.1 (2)	C5—C6—C7—O3	168.28 (19)
N1—Cd1—O5—C8	178.02 (17)	Cd1—O7—C14—O8	176.57 (18)
N2—Cd1—O5—C8	1.47 (16)	Cd1—O7—C14—C13	−1.5 (3)
O7—Cd1—O5—C8	2.8 (2)	C9—N2—C13—C12	0.2 (3)
O1—Cd1—O5—C8	−110.75 (17)	Cd1—N2—C13—C12	178.42 (15)
O3—Cd1—O5—C8	108.19 (17)	C9—N2—C13—C14	179.35 (18)
Cd1—O1—C1—O2	170.55 (18)	Cd1—N2—C13—C14	−2.5 (2)
Cd1—O1—C1—C2	−9.2 (2)	O8—C14—C13—N2	−175.54 (19)
N1—C2—C1—O1	2.1 (3)	O7—C14—C13—N2	2.6 (3)
C3—C2—C1—O1	−175.7 (2)	O8—C14—C13—C12	3.5 (3)
N1—C2—C1—O2	−177.69 (19)	O7—C14—C13—C12	−178.3 (2)
C3—C2—C1—O2	4.6 (3)	Cd1—O5—C8—O6	177.91 (19)
N1—Cd1—O3—C7	−17.16 (14)	Cd1—O5—C8—C9	−1.4 (2)
N2—Cd1—O3—C7	141.91 (15)	N2—C9—C8—O6	−179.1 (2)
O7—Cd1—O3—C7	−148.03 (15)	C10—C9—C8—O6	0.3 (3)
O1—Cd1—O3—C7	−40.58 (19)	N2—C9—C8—O5	0.3 (3)
O5—Cd1—O3—C7	67.86 (15)	C10—C9—C8—O5	179.7 (2)
N1—Cd1—O7—C14	−175.19 (15)	N2—C13—C12—C11	−0.3 (3)
N2—Cd1—O7—C14	0.15 (15)	C14—C13—C12—C11	−179.3 (2)
O1—Cd1—O7—C14	108.04 (17)	N4—C16—C15—N3	167.86 (18)
O3—Cd1—O7—C14	−112.60 (17)	C17—C16—C15—N3	−69.6 (3)
O5—Cd1—O7—C14	−1.2 (2)	C13—C12—C11—C10	0.3 (4)
N1—Cd1—N2—C9	−11.6 (3)	C12—C11—C10—C9	−0.3 (4)
O7—Cd1—N2—C9	179.53 (17)	N2—C9—C10—C11	0.2 (3)
O1—Cd1—N2—C9	80.88 (16)	C8—C9—C10—C11	−179.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O10ⁱ	0.89 (3)	1.90 (3)	2.780 (3)	172 (3)
N3—H3B···O3ⁱⁱ	0.86 (3)	2.04 (3)	2.899 (3)	177 (3)
N3—H3C···O2ⁱ	0.92 (2)	1.89 (2)	2.790 (3)	164 (3)
N4—H4A···O8ⁱⁱ	0.91 (3)	1.96 (3)	2.870 (3)	176 (3)
N4—H4B···O5	0.83 (3)	2.06 (3)	2.889 (3)	172 (3)
N4—H4C···O9ⁱⁱ	0.91 (3)	1.90 (3)	2.803 (3)	170 (3)
O9—H9A···O4ⁱⁱⁱ	0.76 (4)	1.96 (4)	2.708 (3)	170 (4)
O9—H9B···O2^iv	0.84 (4)	2.00 (4)	2.827 (3)	165 (4)
O10—H10A···O6^v	0.88 (6)	2.04 (6)	2.848 (4)	151 (6)
O10—H10B···O8^vi	0.74 (4)	2.19 (4)	2.835 (3)	147 (4)
C10—H10···O3^vii	0.93	2.54	3.298 (3)	139
C12—H12···O1^vi	0.93	2.44	3.200 (3)	139

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

Experimental details

Crystal data
Chemical formula	(C₃H₁₂N₂)[Cd(C₇H₃NO₄)₂]·2H₂O
M_r	554.80
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.6227 (17), 10.133 (2), 13.448 (3)
α, β, γ (°)	81.36 (3), 76.73 (3), 65.38 (3)
V (Å³)	1037.7 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	1.12
Crystal size (mm)	0.3 × 0.2 × 0.15

Data collection
Diffractometer	Stoe IPDS 2T diffractometer
Absorption correction	Numerical (X-SHAPE and X-RED32; Stoe & Cie, 2005)
T_min, T_max	0.764, 0.842
No. of measured, independent and observed [I > 2σ(I)] reflections	11690, 5554, 4562
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.686

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.063, 1.02
No. of reflections	5554
No. of parameters	330
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.50, −0.37

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O10ⁱ	0.89 (3)	1.90 (3)	2.780 (3)	172 (3)
N3—H3B···O3ⁱⁱ	0.86 (3)	2.04 (3)	2.899 (3)	177 (3)
N3—H3C···O2ⁱ	0.924 (18)	1.891 (19)	2.790 (3)	164 (3)
N4—H4A···O8ⁱⁱ	0.91 (3)	1.96 (3)	2.870 (3)	176 (3)
N4—H4B···O5	0.83 (3)	2.06 (3)	2.889 (3)	172 (3)
N4—H4C···O9ⁱⁱ	0.91 (3)	1.90 (3)	2.803 (3)	170 (3)
O9—H9A···O4ⁱⁱⁱ	0.76 (4)	1.96 (4)	2.708 (3)	170 (4)
O9—H9B···O2^iv	0.84 (4)	2.00 (4)	2.827 (3)	165 (4)
O10—H10A···O6^v	0.88 (6)	2.04 (6)	2.848 (4)	151 (6)
O10—H10B···O8^vi	0.74 (4)	2.19 (4)	2.835 (3)	147 (4)
C10—H10···O3^vii	0.93	2.54	3.298 (3)	139
C12—H12···O1^vi	0.93	2.44	3.200 (3)	139

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

Acknowledgements

We are grateful to Tarbiat Moallem University for financial support.

References

Aghabozorg, H., Bagheri, S., Heidari, M., Ghadermazi, M. & Attar Gharamaleki, J. (2008a). Acta Cryst. E64, m1065–m1066. Web of Science CSD CrossRef IUCr Journals Google Scholar
Aghabozorg, H., Ghadermazi, M., Nakhjavan, B. & Manteghi, F. (2008b). J. Chem. Crystallogr. 38, 135–145. CrossRef CAS Google Scholar
Aghabozorg, H., Heidari, M., Bagheri, S., Attar Gharamaleki, J. & Ghadermazi, M. (2008c). Acta Cryst. E64, m874–m875. Web of Science CSD CrossRef IUCr Journals Google Scholar
Aghabozorg, H., Heidari, M., Ghadermazi, M. & Attar Gharamaleki, J. (2008d). Acta Cryst. E64, o1045–o1046. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Pasdar, H., Shakiba, S., Aghabozorg, H. & Notash, B. (2011). Acta Cryst. E67, m587. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2005). X-AREA, X-RED32 and X-SHAPE. Stoe & Cie, Darmstadt, Germany. Google Scholar

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