Poly[aqua­(dimethyl sulfoxide)(μ4-pyridine-2,5-dicarboxyl­ato)calcium(II)]

Pasdar, H.; Safari, Z.; Aghabozorg, H.; Notash, B.; Mirzaei, M.

doi:10.1107/S1600536810054334

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page m221

doi:10.1107/S1600536810054334

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Poly[aqua(dimethyl sulfoxide)(μ₄-pyridine-2,5-dicarboxylato)calcium(II)]

Hoda Pasdar,^a Zahra Safari,^a ^* Hossein Aghabozorg,^a Behrouz Notash ^b and Masoud Mirzaei ^c

^aDepartment of Chemistry, Islamic Azad University, North Tehran Branch, Tehran, Iran, ^bDepartment of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran, 1983963113, Iran, and ^cDepartment of Chemistry, School of Sciences, Ferdowsi University of Mashhad, Mashhad, Iran
^*Correspondence e-mail: z.safari515@yahoo.com

(Received 19 December 2010; accepted 26 December 2010; online 15 January 2011)

In the polymeric title compound, [Ca(C₇H₃NO₄)(H₂O)(C₂H₆OS)]_n, the Ca^II ion is coordinated in a distorted pentagonal–bipyramidal CdNO₆ geometry. The crystal packing is stabilized by O—H⋯O hydrogen bonds and π–π stacking interactions between the aromatic rings of pyridine-2,5-dicarboxylate with centroid–centroid distances of 3.6166 (13) Å.

Related literature

For related coordination polymers involving pyridine-2,5-dicarboxylic acid, see: Aghabozorg, Derikvand et al. (2008 ); Aghabozorg, Manteghi & Sheshmani (2008 ); Xu et al. (2008 ); Sun et al. (2006 ); Çolak et al. (2010 ); Wang et al. (2009 ); Xie et al. (2009 ).

Experimental

Crystal data

[Ca(C₇H₃NO₄)(H₂O)(C₂H₆OS)]
M_r = 301.34
Monoclinic, P 2₁ /c
a = 10.449 (2) Å
b = 11.450 (2) Å
c = 10.325 (2) Å
β = 95.93 (3)°
V = 1228.7 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.70 mm⁻¹
T = 298 K
0.27 × 0.15 × 0.15 mm

Data collection

Stoe IPDS II diffractometer
8616 measured reflections
3302 independent reflections
2718 reflections with I > 2σ(I)
R_int = 0.041

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.097
S = 1.11
3302 reflections
173 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O6—H6B⋯O3ⁱ	0.84 (3)	2.00 (3)	2.782 (2)	155 (3)
O6—H6A⋯O1ⁱⁱ	0.82 (4)	1.96 (4)	2.739 (2)	158 (3)
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{5\over 2}}, z-{\script{1\over 2}}]$ .

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/S1600536810054334/bt5441sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810054334/bt5441Isup2.hkl

checkCIF report

Comment top

Extended frameworks of coordination polymers based on transition metal ions and multifunctional bridging ligands are currently of great interest because of their intriguing topologies and their potential applications (Sun et al., 2006; Wang et al., 2009; Xie, et al., 2009). Pyridine-2,5-dicarboxylic acid (py-2,5- dcH₂) has unique features because of the presence of two carboxylate groups (O donor atoms) and the pyridine ring (N donor atom), which aids to increase the dimensionality of the assembled covalent network. Therefore, it is most likely that py-2,5-dcH₂ will form low symmetric structures with metals (Aghabozorg, Derikvand, et al., 2008; Xu et al., 2008; Çolak et al., 2010). Our research group has recently focused on one-pot synthesis of water soluble self-assembly systems that can function as suitable ligands in the synthesis of metal complexes (Aghabozorg, Manteghi & Sheshmani, 2008).

The title compound consists of one deprotonated 2,5-pydc unit, one water molecule, and one dimethylsulfoxide molecule. The asymmetric unit of the title compound is shown in Fig. 1. In the the title compound, Ca^II ion is 7-coordinated in a NO₆ environment. Its geometry is distorted pentagonal bipyramidal. Pentagonal plane is constructed by one oxygen from water, one nitrogen and three oxygen atoms from the (py-2,5-dc)^2– and axial positions occupied by two oxygen atoms from (py-2,5-dc)^2– and dimethylsulfoxide moieties. A perspective view of the coordination environment around the Ca^II ion is shown in Fig. 2. The crystal structure of title compound shows that the compound is a two-dimensional polymer [Ca(C₇H₃NO₄)(H₂O)(C₂H₆SO)]_n. The polymeric structure of title compound is shown in Fig. 3. There are O—H···O hydrogen bonds between hydrogen atoms of water molecules and oxygen atoms of py-2,5-dc (Table 2). There is also π–π stacking interactions (Fig. 4) between two aromatic rings of (py-2,5-dc)^2– with centroid–centroid distances of 3.6166 (13) Å.

Related literature top

For related coordination polymers involving pyridine-2,5-dicarboxylic acid, see: Aghabozorg, Derikvand et al. (2008); Aghabozorg, Manteghi & Sheshmani (2008); Xu et al. (2008); Sun et al. (2006); Çolak et al. (2010); Wang et al. (2009); Xie et al. (2009).

Experimental top

A mixture of CaCl₂ (0.627 g), pyridine-2,5-dicarboxylic acid (0.1519 g), 1,4-butanediammine (1 ml) in 6 ml DMSO was stirred at room temprature for 2 hrs.The solution was filtered, and the filtrate was stand at room temprature. After two days, colorless block shape crystals of the title compound were obtained (m.p 249°C).

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 asymetric unit of title compound with displacement ellipsoids drawn at 50% probability level.
	Fig. 2. The coordination environment around the Ca(II) ion in the title compound.
	Fig. 3. A view of the two-dimensional structure of the title compound down the a-axis. Hydrogen atoms have been ommited for clarity.
	Fig. 4. The packing diagram of title compound showing intermolecular π-π interaction (dashed lines) between pyridine rings of py-2,5-dc.

Poly[aqua(dimethyl sulfoxide)(µ₄-pyridine-2,5-dicarboxylato)calcium(II)] top

Crystal data top

[Ca(C₇H₃NO₄)(C₂H₆OS)(H₂O)]	F(000) = 624.0
M_r = 301.34	D_x = 1.629 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3302 reflections
a = 10.449 (2) Å	θ = 2.7–29.1°
b = 11.450 (2) Å	µ = 0.70 mm⁻¹
c = 10.325 (2) Å	T = 298 K
β = 95.93 (3)°	Block, colorless
V = 1228.7 (4) Å³	0.27 × 0.15 × 0.15 mm
Z = 4

Data collection top

Stoe IPDS II diffractometer	2718 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.041
Graphite monochromator	θ_max = 29.1°, θ_min = 2.7°
Detector resolution: 0.15 mm pixels mm^-1	h = −14→13
rotation method scans	k = −13→15
8616 measured reflections	l = −14→14
3302 independent 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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ²(F_o²) + (0.0423P)² + 0.5537P] where P = (F_o² + 2F_c²)/3
3302 reflections	(Δ/σ)_max = 0.001
173 parameters	Δρ_max = 0.44 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

[Ca(C₇H₃NO₄)(C₂H₆OS)(H₂O)]	V = 1228.7 (4) Å³
M_r = 301.34	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.449 (2) Å	µ = 0.70 mm⁻¹
b = 11.450 (2) Å	T = 298 K
c = 10.325 (2) Å	0.27 × 0.15 × 0.15 mm
β = 95.93 (3)°

Data collection top

Stoe IPDS II diffractometer	2718 reflections with I > 2σ(I)
8616 measured reflections	R_int = 0.041
3302 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.097	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	Δρ_max = 0.44 e Å⁻³
3302 reflections	Δρ_min = −0.30 e Å⁻³
173 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	0.67926 (4)	1.08747 (3)	0.15351 (3)	0.01937 (10)
S1	1.00299 (7)	0.95463 (8)	0.23803 (8)	0.0533 (2)
O5	0.89654 (19)	1.04175 (19)	0.2093 (2)	0.0525 (5)
C9	0.9931 (4)	0.8533 (4)	0.1082 (4)	0.0836 (13)
H9A	0.9068	0.8237	0.0933	0.125*
H9B	1.0515	0.7899	0.1298	0.125*
H9C	1.0155	0.8914	0.0308	0.125*
C8	0.9511 (5)	0.8595 (5)	0.3569 (5)	0.114 (2)
H8A	0.9386	0.9031	0.4340	0.171*
H8B	1.0151	0.8003	0.3777	0.171*
H8C	0.8715	0.8234	0.3237	0.171*
N1	0.63254 (17)	0.97721 (13)	0.36682 (15)	0.0212 (3)
C5	0.6057 (2)	0.86315 (16)	0.37822 (17)	0.0207 (4)
H5	0.5735	0.8228	0.3037	0.025*
C1	0.67172 (18)	1.03533 (15)	0.47695 (17)	0.0176 (3)
C3	0.6660 (2)	0.86337 (17)	0.60687 (18)	0.0245 (4)
H3	0.6803	0.8252	0.6866	0.029*
C2	0.6872 (2)	0.98248 (17)	0.59788 (18)	0.0237 (4)
H2	0.7114	1.0262	0.6723	0.028*
C4	0.62317 (19)	0.80212 (15)	0.49489 (17)	0.0191 (3)
C7	0.59970 (19)	0.67151 (16)	0.49754 (18)	0.0203 (4)
O3	0.53823 (15)	0.62711 (12)	0.39822 (14)	0.0265 (3)
O4	0.64566 (17)	0.61761 (13)	0.59638 (14)	0.0311 (4)
O2	0.72123 (17)	1.22148 (12)	0.56666 (14)	0.0307 (3)
O1	0.69341 (17)	1.20480 (12)	0.34958 (13)	0.0307 (3)
C6	0.6974 (2)	1.16520 (15)	0.46351 (18)	0.0209 (4)
O6	0.7022 (2)	1.06481 (15)	−0.07874 (15)	0.0350 (4)
H6A	0.685 (3)	1.127 (3)	−0.116 (3)	0.055 (9)*
H6B	0.643 (3)	1.019 (3)	−0.106 (3)	0.043 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ca1	0.0298 (2)	0.01175 (16)	0.01607 (16)	0.00106 (14)	−0.00007 (13)	0.00002 (13)
S1	0.0306 (3)	0.0622 (5)	0.0649 (5)	0.0089 (3)	−0.0054 (3)	−0.0029 (4)
O5	0.0371 (10)	0.0517 (12)	0.0662 (13)	0.0085 (9)	−0.0062 (9)	−0.0013 (10)
C9	0.077 (3)	0.074 (3)	0.103 (3)	0.005 (2)	0.025 (2)	−0.026 (2)
C8	0.109 (4)	0.128 (4)	0.109 (4)	0.062 (3)	0.038 (3)	0.066 (3)
N1	0.0341 (9)	0.0119 (7)	0.0173 (7)	−0.0012 (6)	0.0011 (6)	0.0000 (5)
C5	0.0321 (10)	0.0128 (8)	0.0169 (8)	−0.0009 (7)	0.0012 (7)	−0.0013 (6)
C1	0.0235 (9)	0.0118 (8)	0.0177 (8)	0.0012 (6)	0.0026 (7)	−0.0012 (6)
C3	0.0383 (11)	0.0187 (9)	0.0159 (8)	−0.0018 (8)	0.0000 (8)	0.0034 (7)
C2	0.0371 (11)	0.0170 (8)	0.0165 (8)	−0.0043 (8)	0.0000 (7)	−0.0022 (7)
C4	0.0252 (9)	0.0122 (8)	0.0200 (8)	0.0005 (7)	0.0034 (7)	0.0013 (6)
C7	0.0280 (10)	0.0133 (8)	0.0200 (8)	0.0001 (7)	0.0049 (7)	0.0014 (6)
O3	0.0342 (8)	0.0172 (6)	0.0272 (7)	−0.0041 (6)	−0.0019 (6)	−0.0016 (5)
O4	0.0573 (10)	0.0150 (6)	0.0203 (7)	0.0015 (6)	−0.0002 (7)	0.0039 (5)
O2	0.0549 (10)	0.0151 (6)	0.0212 (7)	−0.0016 (6)	0.0003 (6)	−0.0042 (5)
O1	0.0598 (10)	0.0131 (6)	0.0191 (6)	−0.0043 (6)	0.0029 (7)	0.0003 (5)
C6	0.0307 (10)	0.0116 (8)	0.0206 (8)	0.0003 (7)	0.0031 (7)	−0.0021 (6)
O6	0.0622 (12)	0.0181 (7)	0.0253 (7)	−0.0083 (8)	0.0076 (7)	−0.0010 (6)

Geometric parameters (Å, º) top

Ca1—O3ⁱ	2.3249 (16)	C5—C4	1.388 (2)
Ca1—O5	2.343 (2)	C5—H5	0.9300
Ca1—O1	2.4214 (15)	C1—C2	1.382 (3)
Ca1—O2ⁱⁱ	2.4215 (15)	C1—C6	1.520 (2)
Ca1—O4ⁱⁱⁱ	2.4377 (15)	C3—C2	1.386 (3)
Ca1—O6	2.4484 (17)	C3—C4	1.386 (3)
Ca1—N1	2.6278 (16)	C3—H3	0.9300
Ca1—H6B	2.78 (3)	C2—H2	0.9300
S1—O5	1.501 (2)	C4—C7	1.516 (2)
S1—C8	1.768 (5)	C7—O4	1.246 (2)
S1—C9	1.768 (4)	C7—O3	1.260 (2)
C9—H9A	0.9600	O3—Ca1^iv	2.3249 (16)
C9—H9B	0.9600	O4—Ca1^v	2.4377 (15)
C9—H9C	0.9600	O2—C6	1.248 (2)
C8—H8A	0.9600	O2—Ca1^vi	2.4215 (15)
C8—H8B	0.9600	O1—C6	1.257 (2)
C8—H8C	0.9600	O6—H6A	0.82 (4)
N1—C5	1.344 (2)	O6—H6B	0.84 (3)
N1—C1	1.344 (2)

O3ⁱ—Ca1—O5	178.05 (7)	S1—C8—H8A	109.5
O3ⁱ—Ca1—O1	93.30 (6)	S1—C8—H8B	109.5
O5—Ca1—O1	86.82 (7)	H8A—C8—H8B	109.5
O3ⁱ—Ca1—O2ⁱⁱ	87.06 (6)	S1—C8—H8C	109.5
O5—Ca1—O2ⁱⁱ	94.87 (7)	H8A—C8—H8C	109.5
O1—Ca1—O2ⁱⁱ	79.09 (5)	H8B—C8—H8C	109.5
O3ⁱ—Ca1—O4ⁱⁱⁱ	91.12 (6)	C5—N1—C1	117.08 (16)
O5—Ca1—O4ⁱⁱⁱ	87.47 (7)	C5—N1—Ca1	126.80 (12)
O1—Ca1—O4ⁱⁱⁱ	137.02 (5)	C1—N1—Ca1	113.85 (11)
O2ⁱⁱ—Ca1—O4ⁱⁱⁱ	143.87 (5)	N1—C5—C4	123.73 (17)
O3ⁱ—Ca1—O6	89.31 (7)	N1—C5—H5	118.1
O5—Ca1—O6	91.53 (8)	C4—C5—H5	118.1
O1—Ca1—O6	150.93 (5)	N1—C1—C2	122.99 (16)
O2ⁱⁱ—Ca1—O6	72.13 (5)	N1—C1—C6	116.64 (16)
O4ⁱⁱⁱ—Ca1—O6	71.77 (5)	C2—C1—C6	120.37 (16)
O3ⁱ—Ca1—N1	91.41 (6)	C2—C3—C4	118.80 (17)
O5—Ca1—N1	86.89 (7)	C2—C3—H3	120.6
O1—Ca1—N1	64.30 (5)	C4—C3—H3	120.6
O2ⁱⁱ—Ca1—N1	143.22 (5)	C1—C2—C3	119.12 (18)
O4ⁱⁱⁱ—Ca1—N1	72.87 (5)	C1—C2—H2	120.4
O6—Ca1—N1	144.64 (5)	C3—C2—H2	120.4
O3ⁱ—Ca1—H6B	78.5 (6)	C3—C4—C5	118.12 (17)
O5—Ca1—H6B	102.0 (6)	C3—C4—C7	121.52 (16)
O1—Ca1—H6B	162.4 (7)	C5—C4—C7	120.34 (17)
O2ⁱⁱ—Ca1—H6B	84.9 (7)	O4—C7—O3	126.02 (18)
O4ⁱⁱⁱ—Ca1—H6B	59.5 (7)	O4—C7—C4	117.00 (18)
O6—Ca1—H6B	17.1 (7)	O3—C7—C4	116.95 (17)
N1—Ca1—H6B	130.7 (7)	C7—O3—Ca1^iv	132.07 (13)
O5—S1—C8	105.83 (18)	C7—O4—Ca1^v	135.17 (13)
O5—S1—C9	107.57 (19)	C6—O2—Ca1^vi	139.02 (14)
C8—S1—C9	97.1 (3)	C6—O1—Ca1	125.13 (12)
S1—O5—Ca1	151.24 (14)	O2—C6—O1	126.64 (17)
S1—C9—H9A	109.5	O2—C6—C1	116.68 (16)
S1—C9—H9B	109.5	O1—C6—C1	116.68 (16)
H9A—C9—H9B	109.5	Ca1—O6—H6A	110 (2)
S1—C9—H9C	109.5	Ca1—O6—H6B	105 (2)
H9A—C9—H9C	109.5	H6A—O6—H6B	106 (3)
H9B—C9—H9C	109.5

C8—S1—O5—Ca1	−51.3 (4)	C4—C3—C2—C1	−3.5 (3)
C9—S1—O5—Ca1	51.7 (3)	C2—C3—C4—C5	1.1 (3)
O1—Ca1—O5—S1	124.5 (3)	C2—C3—C4—C7	179.23 (19)
O2ⁱⁱ—Ca1—O5—S1	−156.7 (3)	N1—C5—C4—C3	2.6 (3)
O4ⁱⁱⁱ—Ca1—O5—S1	−12.9 (3)	N1—C5—C4—C7	−175.50 (18)
O6—Ca1—O5—S1	−84.5 (3)	C3—C4—C7—O4	−14.9 (3)
N1—Ca1—O5—S1	60.1 (3)	C5—C4—C7—O4	163.15 (18)
O3ⁱ—Ca1—N1—C5	89.08 (17)	C3—C4—C7—O3	166.78 (19)
O5—Ca1—N1—C5	−89.97 (18)	C5—C4—C7—O3	−15.2 (3)
O1—Ca1—N1—C5	−177.93 (18)	O4—C7—O3—Ca1^iv	88.3 (2)
O2ⁱⁱ—Ca1—N1—C5	176.05 (15)	C4—C7—O3—Ca1^iv	−93.54 (19)
O4ⁱⁱⁱ—Ca1—N1—C5	−1.66 (16)	O3—C7—O4—Ca1^v	10.8 (3)
O6—Ca1—N1—C5	−1.7 (2)	C4—C7—O4—Ca1^v	−167.38 (13)
O3ⁱ—Ca1—N1—C1	−108.68 (14)	O3ⁱ—Ca1—O1—C6	103.41 (18)
O5—Ca1—N1—C1	72.27 (14)	O5—Ca1—O1—C6	−74.64 (18)
O1—Ca1—N1—C1	−15.69 (13)	O2ⁱⁱ—Ca1—O1—C6	−170.23 (18)
O2ⁱⁱ—Ca1—N1—C1	−21.71 (19)	O4ⁱⁱⁱ—Ca1—O1—C6	8.2 (2)
O4ⁱⁱⁱ—Ca1—N1—C1	160.58 (14)	O6—Ca1—O1—C6	−162.06 (16)
O6—Ca1—N1—C1	160.53 (13)	N1—Ca1—O1—C6	13.44 (16)
C1—N1—C5—C4	−3.8 (3)	Ca1^vi—O2—C6—O1	37.1 (4)
Ca1—N1—C5—C4	157.96 (15)	Ca1^vi—O2—C6—C1	−143.44 (16)
C5—N1—C1—C2	1.2 (3)	Ca1—O1—C6—O2	170.04 (17)
Ca1—N1—C1—C2	−162.86 (15)	Ca1—O1—C6—C1	−9.4 (3)
C5—N1—C1—C6	−177.95 (17)	N1—C1—C6—O2	173.06 (18)
Ca1—N1—C1—C6	18.0 (2)	C2—C1—C6—O2	−6.1 (3)
N1—C1—C2—C3	2.4 (3)	N1—C1—C6—O1	−7.5 (3)
C6—C1—C2—C3	−178.49 (18)	C2—C1—C6—O1	173.34 (19)

Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x, −y+5/2, z−1/2; (iii) x, −y+3/2, z−1/2; (iv) −x+1, y−1/2, −z+1/2; (v) x, −y+3/2, z+1/2; (vi) x, −y+5/2, z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O6—H6B···O3ⁱⁱⁱ	0.84 (3)	2.00 (3)	2.782 (2)	155 (3)
O6—H6A···O1ⁱⁱ	0.82 (4)	1.96 (4)	2.739 (2)	158 (3)

Symmetry codes: (ii) x, −y+5/2, z−1/2; (iii) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	[Ca(C₇H₃NO₄)(C₂H₆OS)(H₂O)]
M_r	301.34
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	10.449 (2), 11.450 (2), 10.325 (2)
β (°)	95.93 (3)
V (Å³)	1228.7 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.70
Crystal size (mm)	0.27 × 0.15 × 0.15

Data collection
Diffractometer	Stoe IPDS II diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	8616, 3302, 2718
R_int	0.041
(sin θ/λ)_max (Å⁻¹)	0.685

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.097, 1.11
No. of reflections	3302
No. of parameters	173
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.44, −0.30

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
O6—H6B···O3ⁱ	0.84 (3)	2.00 (3)	2.782 (2)	155 (3)
O6—H6A···O1ⁱⁱ	0.82 (4)	1.96 (4)	2.739 (2)	158 (3)

Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x, −y+5/2, z−1/2.

Acknowledgements

The authors gratefully acknowledge the Islamic Azad University, North Tehran Branch, for financial support and Shahid Beheshti University for the provision of X-ray facilities.

References

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