Poly[aqua-(dimethyl sulfoxide)(μ(4)-pyridine-2,5-dicarboxyl-ato)calcium(II)].

In the polymeric title compound, [Ca(C(7)H(3)NO(4))(H(2)O)(C(2)H(6)OS)](n), the Ca(II) ion is coordinated in a distorted penta-gonal-bipyramidal CdNO(6) geometry. The crystal packing is stabilized by O-H⋯O hydrogen bonds and π-π stacking inter-actions between the aromatic rings of pyridine-2,5-dicarb-oxy-late 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 = 301.34

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.097

S = 1.11

3302 reflections

173 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.44 e Å−3

Δρmin = −0.30 e Å−3

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 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810054334/bt5441sup1.cif

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Ca(C7H3NO4)(C2H6OS)(H2O)]	F(000) = 624.0
Mr = 301.34	Dx = 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

Stoe IPDS II diffractometer	2718 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.041
graphite	θmax = 29.1°, θmin = 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 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(Fo2) + (0.0423P)2 + 0.5537P] where P = (Fo2 + 2Fc2)/3
3302 reflections	(Δ/σ)max = 0.001
173 parameters	Δρmax = 0.44 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

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.

	x	y	z	Uiso*/Ueq
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)*

	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)

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—Ca1iv	2.3249 (16)
C9—H9B	0.9600	O4—Ca1v	2.4377 (15)
C9—H9C	0.9600	O2—C6	1.248 (2)
C8—H8A	0.9600	O2—Ca1vi	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—Ca1iv	132.07 (13)
O5—S1—C8	105.83 (18)	C7—O4—Ca1v	135.17 (13)
O5—S1—C9	107.57 (19)	C6—O2—Ca1vi	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—Ca1iv	88.3 (2)
O2ii—Ca1—N1—C5	176.05 (15)	C4—C7—O3—Ca1iv	−93.54 (19)
O4iii—Ca1—N1—C5	−1.66 (16)	O3—C7—O4—Ca1v	10.8 (3)
O6—Ca1—N1—C5	−1.7 (2)	C4—C7—O4—Ca1v	−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)	Ca1vi—O2—C6—O1	37.1 (4)
Ca1—N1—C5—C4	157.96 (15)	Ca1vi—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)

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)

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) ; (ii) .