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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 12| December 2011| Pages m1736-m1737
https://doi.org/10.1107/S1600536811046940

Calcium acamprosate: a triclinic polymorph

Elisabetta Maccaroni,a Walter Panzerib and Luciana Malpezzia*

aDepartment of Chemistry, Materials and Chemical Engineering "G. Natta", Politecnico di Milano, Via Mancinelli 7, I-20131 Milano, Italy, and bIstituto di Chimica del Riconoscimento Molecolare sezione "A. Quilico", CNR, Via Mancinelli 7, I-20131 Milano, Italy
*Correspondence e-mail: luciana.malpezzi@polimi.it

(Received 3 October 2011; accepted 7 November 2011; online 9 November 2011)

The title compound, poly[bis­(μ3-4-acetamido­propane­sulfon­ato)­calcium], [Ca(C5H10NO4S)2]n, is a triclinic polymorph of the previously reported monoclinic structure [Toffoli et al. (1988[Toffoli, P., Rodier, N., Ceolin, R., Ladure, P. & Tran, G. (1988). Acta Cryst. C44, 1493-1494.]). Acta Cryst. C44, 1493–1494]. The triclinic modification was found to have an all-trans configuration of the acetamido­propane chain, in contrast with the monoclinic polymorph which shows an angle of 74.66 (8)° between the S—C—C—C chain plane and that of the amide group. The Ca2+ cation is situated on an inversion centre and is hexa­coordinated by six O atoms belonging to different anions in a distorted octa­hedral geometry. This arrangement leads to a layered structure parallel to (011). The layers are held together by N—H⋯O hydrogen bonds and by short C—H⋯O inter­actions, both involving the sulfonate O atoms not coordinated to the Ca2+ cations. The structure was determined from a crystal twinned by non-merohedry [twin law ([\overline{1}]00, 0[\overline{1}]0, −0.335 −0.85 1), with a fractional contribution of the minor twin domain of 46.7 (1)%].

Related literature

For the characterization of the monclinic polymorph and related structures, see: Toffoli et al. (1988[Toffoli, P., Rodier, N., Ceolin, R., Ladure, P. & Tran, G. (1988). Acta Cryst. C44, 1493-1494.]). The title compound is a drug used successfully in the treatment of alcoholism. For the synthesis, see: Laboratorio Chimico Inter­nazionale SpA (2010[Laboratorio Chimico Internazionale SpA (2010). Patent No. WO2010/035094.]). For its therapeutic effect and a tolerability study, see: Rösner et al. (2010[Rösner, S., Hackl-Herrwerth, A., Leucht, S., Lehert, P., Vecchi, S. & Soyka, M. (2010). Cochrane Database Syst. Rev. 9, 1-119.]). For proposed mechanisms of action, see: De Witte et al. (2005[De Witte, P., Littleton, J., Parot, P. & Koob, G. (2005). CNS Drugs, 19, 517-537.]). Programs used for identifying the twin system were PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]) and CELL_NOW (Bruker, 2008[Bruker (2008). CELL_NOW and TWINABS. Bruker AXS Inc., Madison, Wisconsin, USA.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]).

[Scheme 1]

Experimental

Crystal data

  • [Ca(C5H10NO4S)2]

  • Mr = 400.48

  • Triclinic, [P \overline 1]

  • a = 5.5372 (4) Å

  • b = 8.1487 (6) Å

  • c = 9.7578 (7) Å

  • α = 69.159 (1)°

  • β = 84.305 (2)°

  • γ = 89.329 (2)°

  • V = 409.31 (5) Å3

  • Z = 1

  • Mo Kα radiation

  • μ = 0.68 mm−1

  • T = 293 K

  • 0.29 × 0.23 × 0.08 mm
Data collection

  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (TWINABS; Bruker, 2008[Bruker (2008). CELL_NOW and TWINABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.827, Tmax = 0.948

  • 22542 measured reflections

  • 8721 independent reflections

  • 7647 reflections with I > 2σ(I)

  • Rint = 0.027
Refinement

  • R[F2 > 2σ(F2)] = 0.034

  • wR(F2) = 0.088

  • S = 1.02

  • 8721 reflections

  • 109 parameters

  • H-atom parameters constrained

  • Δρmax = 0.39 e Å−3

  • Δρmin = −0.33 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N—H1N⋯O1i 0.86 2.15 3.0025 (12) 169
C5—H5C⋯O1i 0.96 2.48 3.3569 (15) 152
C1—H1B⋯O1ii 0.97 2.53 3.3007 (14) 137
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y+1, -z+1.

Data collection: SMART (Bruker, 2003[Bruker (2003). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2003[Bruker (2003). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999[Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115-119.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL/NT (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811046940/zl2412sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811046940/zl2412Isup2.hkl

checkCIF report


Comment top

Calcium acamprosate (Fig. 1), systematic name: calcium bis(3-acetylamino-propane)-1-sulphonate, also known as N-acetyl homotaurine, is a white crystalline synthetic compound which crystallizes as discrete acetylamino-propane-sulphonate anions, (C5H10N O4S)-, and Ca2+ cations, connected by Ca···O interactions. It is used in the treatment of alcoholism and it is specifically indicated for the maintenance of abstinence from alcohol in patients with alcohol dependence (Rösner et al., 2010). The mechanism of action of calcium acamprosate in prevention of relapses is not completely understood, but it is believed to restore the normal chemical balance between neuronal excitation and inhibition that would be disrupted by long-term or chronic alcohol abuse. In other words, it helps the brain begin working normally again (De Witte et al., 2005).

A monoclinic polymorph (A) of the title compound has been previously reported (Toffoli et al. 1988). The new polymorph form (B) crystallizes in the centrosymmetric P1 space group with the Ca2+ located on a crystallographic inversion centre, so there is only one single anion in the asymmetric unit of the elementary cell. The conformation of the acetylamino-propane chain shows the main geometric difference between polymorph A and polymorph B: in the triclinic modification (B) the conformation is all trans, while in the monoclinic form (A) an angle of 74.66 (8)° between the S—C—C—C chain plane and that of the amide group was found. Bond lengths and angles are within normal ranges (Allen et al., 1987) and are comparable with those of polymorph (A). Each Ca2+ cation is coordinated in a distorted octahedral geometry to six different anions via Ca···O interactions with four sulfonyl O atoms and two carbonyl O atoms with a Ca···O distance in the range 2.283 (1)–2.394 (1) Å. The coordination of the Ca2+ cations to two terminal sides of the anions leads to a polymeric bidimensional structure extended in layers parallel to the (011) plane. The layers are connected into a three-dimensional network by N—H···O hydrogen bonds and by short C—H···O interactions, both involving the sulfonyl O atoms not coordinated to the Ca2+ cations.

Related literature top

For the characterization of the monclinic polymorph and related structures, see: Toffoli et al. (1988). The title compound is a drug used successfully in the treatment of alcoholism. For the synthesis, see: Laboratorio Chimico Internazionale SpA (2010). For its therapeutic effect and a tolerability study, see: Rösner et al. (2010). For proposed mechanisms of action, see: De Witte et al. (2005). Programs used for identifying the twin system were PLATON (Spek, 2009) and CELL_NOW (Bruker, 2008). For standard bond lengths, see: Allen et al. (1987).

Experimental top

The title compound was prepared according to the procedure patented by Laboratorio Chimico Internazionale SpA (2010). Polymorph B precipitates by adding 500 ml of isopropyl alcohol to a water solution of calcium acamprosate kept at 348–353 K and stirred for 53 h. The white solid obtained was filtered hot (348–353 K) and purified by washing with 300 ml of a 75/25 solution (preheated to 343 K) of isopropyl alcohol and deionized water. The wet product was dried under reduced pressure for 6 h at 318 K. Some crystals were suitable for single-crystal XR analysis. The XRPD pattern, carried out on the crystalline powder of this product, is completely in agreement with the powder pattern calculated from the data obtained by single-crystal XR analysis, thus confirming the purity of the crystalline phase of the batch.

Refinement top

The crystal under investigation was found to be non-merohedrally twinned. All reflections for both domains (10284 total) were integrated using Saint, obtaining a number of 4143 reflections (1692 unique ones) for component 1 only (mean I/σ = 12.3), 4146 reflections (1702 unique ones) for component 2 only (mean I/σ = 12.1) and 1974 reflections (929 unique ones) involving both components (mean I/σ = 16.7). The twin law (-1 0 0 0 - 1 0 - 0.335 - 0.85 1) was obtained by the TwinRotMat routine of the PLATON software (Spek, 2009). The orientation matrices for the two components were identified using the program CELL_NOW (Bruker, 2008), with the two twin components resulting related by a 180° rotation around the reciprocal c axis. The reflection data were corrected for absorption using TWINABS (Bruker, 2008), obtaining the HKLF-5 type list of reflections (Sheldrick, 2008) with twin-contributor indicators. The structure was solved using direct methods with only the non-overlapping reflections of component 1 and refined with all reflections of component 1, including the overlapping ones. The fractional contribution of the minor twin component refined to 46.7 (1). H atoms were placed in calculated positions and refined in a riding model with C—H distances of 0.96–0.97 Å and and N—H distance of 0.86 Å. All H atoms were refined with Uiso(H) values equal to 1.5 Ueq of the carrier atom for the methyl group and 1.2 Ueq for all remaining atoms.

Structure description top

Calcium acamprosate (Fig. 1), systematic name: calcium bis(3-acetylamino-propane)-1-sulphonate, also known as N-acetyl homotaurine, is a white crystalline synthetic compound which crystallizes as discrete acetylamino-propane-sulphonate anions, (C5H10N O4S)-, and Ca2+ cations, connected by Ca···O interactions. It is used in the treatment of alcoholism and it is specifically indicated for the maintenance of abstinence from alcohol in patients with alcohol dependence (Rösner et al., 2010). The mechanism of action of calcium acamprosate in prevention of relapses is not completely understood, but it is believed to restore the normal chemical balance between neuronal excitation and inhibition that would be disrupted by long-term or chronic alcohol abuse. In other words, it helps the brain begin working normally again (De Witte et al., 2005).

A monoclinic polymorph (A) of the title compound has been previously reported (Toffoli et al. 1988). The new polymorph form (B) crystallizes in the centrosymmetric P1 space group with the Ca2+ located on a crystallographic inversion centre, so there is only one single anion in the asymmetric unit of the elementary cell. The conformation of the acetylamino-propane chain shows the main geometric difference between polymorph A and polymorph B: in the triclinic modification (B) the conformation is all trans, while in the monoclinic form (A) an angle of 74.66 (8)° between the S—C—C—C chain plane and that of the amide group was found. Bond lengths and angles are within normal ranges (Allen et al., 1987) and are comparable with those of polymorph (A). Each Ca2+ cation is coordinated in a distorted octahedral geometry to six different anions via Ca···O interactions with four sulfonyl O atoms and two carbonyl O atoms with a Ca···O distance in the range 2.283 (1)–2.394 (1) Å. The coordination of the Ca2+ cations to two terminal sides of the anions leads to a polymeric bidimensional structure extended in layers parallel to the (011) plane. The layers are connected into a three-dimensional network by N—H···O hydrogen bonds and by short C—H···O interactions, both involving the sulfonyl O atoms not coordinated to the Ca2+ cations.

For the characterization of the monclinic polymorph and related structures, see: Toffoli et al. (1988). The title compound is a drug used successfully in the treatment of alcoholism. For the synthesis, see: Laboratorio Chimico Internazionale SpA (2010). For its therapeutic effect and a tolerability study, see: Rösner et al. (2010). For proposed mechanisms of action, see: De Witte et al. (2005). Programs used for identifying the twin system were PLATON (Spek, 2009) and CELL_NOW (Bruker, 2008). For standard bond lengths, see: Allen et al. (1987).

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL/NT (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the calcium acamprosate salt (B), showing the anion and cation of the asymmetric unit and the second anion, labeled with a prime symbol, generated by the symmetry operation [1 - x, 2 - y, 1 - z], to complete the unit formula.
[Figure 2] Fig. 2. A view of the crystal packing of calcium acamprosate (B), showing a layer of the two dimensional structure running parallel to the (011) plane.
[Figure 3] Fig. 3. Crystal packing of calcium acamprosate (B), viewed along a axis. N—H···O1 hydrogen bonds and C—H···O1 short interactions are shown as dashed lines.
poly[bis(µ3-4-acetamidopropanesulfonato)calcium] top
Crystal data top
[Ca(C5H10NO4S)2]Z = 1
Mr = 400.48F(000) = 210
Triclinic, P1Dx = 1.625 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71069 Å
a = 5.5372 (4) ÅCell parameters from 4793 reflections
b = 8.1487 (6) Åθ = 2.3–27.1°
c = 9.7578 (7) ŵ = 0.68 mm−1
α = 69.159 (1)°T = 293 K
β = 84.305 (2)°Plate, colourless
γ = 89.329 (2)°0.29 × 0.23 × 0.08 mm
V = 409.31 (5) Å3
Data collection top
Bruker SMART APEX CCD
diffractometer		8721 independent reflections
Radiation source: fine-focus sealed tube7647 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.027
ω scansθmax = 27.5°, θmin = 2.2°
Absorption correction: multi-scan
(TWINABS; Bruker, 2008)		h = −7→7
Tmin = 0.827, Tmax = 0.948k = −10→10
22542 measured reflectionsl = −12→12
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.034Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.088H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0478P)2]
where P = (Fo2 + 2Fc2)/3
8721 reflections(Δ/σ)max = 0.006
109 parametersΔρmax = 0.39 e Å−3
0 restraintsΔρmin = −0.33 e Å−3
Crystal data top
[Ca(C5H10NO4S)2]γ = 89.329 (2)°
Mr = 400.48V = 409.31 (5) Å3
Triclinic, P1Z = 1
a = 5.5372 (4) ÅMo Kα radiation
b = 8.1487 (6) ŵ = 0.68 mm−1
c = 9.7578 (7) ÅT = 293 K
α = 69.159 (1)°0.29 × 0.23 × 0.08 mm
β = 84.305 (2)°
Data collection top
Bruker SMART APEX CCD
diffractometer		8721 independent reflections
Absorption correction: multi-scan
(TWINABS; Bruker, 2008)		7647 reflections with I > 2σ(I)
Tmin = 0.827, Tmax = 0.948Rint = 0.027
22542 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.088H-atom parameters constrained
S = 1.02Δρmax = 0.39 e Å−3
8721 reflectionsΔρmin = −0.33 e Å−3
109 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
xyzUiso*/Ueq
Ca1.00000.50000.00000.02008 (8)
S0.46696 (4)0.53055 (3)0.23925 (3)0.02053 (7)
O10.39518 (14)0.65813 (9)0.30610 (8)0.03333 (19)
O20.71997 (12)0.55429 (9)0.17559 (8)0.02862 (18)
O30.30448 (15)0.52304 (11)0.13414 (8)0.0383 (2)
O40.06178 (14)−0.20198 (9)0.83520 (8)0.0340 (2)
N−0.01015 (17)0.07771 (11)0.69942 (10)0.0334 (2)
H1N−0.10870.16300.68660.040*
C10.44992 (19)0.32245 (13)0.38187 (11)0.0257 (2)
H1A0.47960.23270.33880.031*
H1B0.57690.31650.44500.031*
C20.20568 (19)0.28297 (13)0.47557 (12)0.0282 (2)
H2A0.17420.37190.51930.034*
H2B0.07760.28600.41380.034*
C30.20577 (19)0.10418 (14)0.59580 (12)0.0305 (3)
H3A0.21080.01380.55240.037*
H3B0.34930.09460.64740.037*
C4−0.0642 (2)−0.07020 (14)0.81257 (12)0.0294 (3)
C5−0.2877 (2)−0.07026 (17)0.91136 (14)0.0541 (4)
H5A−0.2469−0.09981.01050.081*
H5B−0.4034−0.15530.90800.081*
H5C−0.35660.04420.87910.081*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ca0.01787 (15)0.02063 (15)0.01751 (15)−0.00083 (11)0.00031 (11)−0.00214 (12)
S0.01931 (13)0.02153 (13)0.01727 (13)−0.00037 (10)0.00084 (10)−0.00333 (10)
O10.0406 (5)0.0242 (4)0.0332 (4)0.0049 (3)0.0042 (4)−0.0100 (3)
O20.0207 (4)0.0316 (4)0.0274 (4)−0.0034 (3)0.0064 (3)−0.0052 (3)
O30.0328 (4)0.0520 (5)0.0267 (4)−0.0053 (4)−0.0088 (4)−0.0081 (4)
O40.0360 (5)0.0221 (4)0.0337 (5)0.0035 (3)0.0052 (4)0.0001 (3)
N0.0362 (6)0.0223 (5)0.0295 (5)0.0062 (4)0.0106 (4)0.0018 (4)
C10.0271 (6)0.0208 (5)0.0229 (5)0.0011 (4)0.0026 (5)−0.0016 (4)
C20.0254 (6)0.0244 (6)0.0265 (6)−0.0001 (4)0.0047 (5)−0.0006 (5)
C30.0309 (6)0.0235 (6)0.0284 (6)−0.0001 (4)0.0065 (5)−0.0011 (5)
C40.0339 (6)0.0225 (6)0.0247 (6)−0.0003 (5)0.0047 (5)−0.0019 (5)
C50.0578 (9)0.0355 (7)0.0443 (8)0.0108 (6)0.0261 (7)0.0076 (6)
Geometric parameters (Å, º) top
Ca—O3i2.2828 (8)N—C31.4523 (13)
Ca—O3ii2.2828 (8)N—H1N0.8600
Ca—O2iii2.3519 (7)C1—C21.5245 (13)
Ca—O22.3519 (7)C1—H1A0.9700
Ca—O4iv2.3941 (7)C1—H1B0.9700
Ca—O4v2.3941 (7)C2—C31.5109 (14)
S—O11.4442 (7)C2—H2A0.9700
S—O31.4471 (8)C2—H2B0.9700
S—O21.4609 (7)C3—H3A0.9700
S—C11.7662 (10)C3—H3B0.9700
O3—Cavi2.2828 (8)C4—C51.4910 (16)
O4—C41.2382 (12)C5—H5A0.9600
O4—Cavii2.3941 (7)C5—H5B0.9600
N—C41.3256 (13)C5—H5C0.9600
O3i—Ca—O3ii180.00 (4)C2—C1—S113.33 (7)
O3i—Ca—O2iii88.69 (3)C2—C1—H1A108.9
O3ii—Ca—O2iii91.31 (3)S—C1—H1A108.9
O3i—Ca—O291.31 (3)C2—C1—H1B108.9
O3ii—Ca—O288.69 (3)S—C1—H1B108.9
O2iii—Ca—O2180.000 (1)H1A—C1—H1B107.7
O3i—Ca—O4iv92.36 (3)C3—C2—C1110.28 (8)
O3ii—Ca—O4iv87.64 (3)C3—C2—H2A109.6
O2iii—Ca—O4iv97.35 (3)C1—C2—H2A109.6
O2—Ca—O4iv82.65 (3)C3—C2—H2B109.6
O3i—Ca—O4v87.64 (3)C1—C2—H2B109.6
O3ii—Ca—O4v92.36 (3)H2A—C2—H2B108.1
O2iii—Ca—O4v82.65 (3)N—C3—C2110.46 (8)
O2—Ca—O4v97.35 (3)N—C3—H3A109.6
O4iv—Ca—O4v180.00 (2)C2—C3—H3A109.6
O1—S—O3112.42 (5)N—C3—H3B109.6
O1—S—O2112.71 (5)C2—C3—H3B109.6
O3—S—O2111.72 (5)H3A—C3—H3B108.1
O1—S—C1107.12 (5)O4—C4—N122.27 (10)
O3—S—C1106.99 (5)O4—C4—C5121.44 (10)
O2—S—C1105.35 (5)N—C4—C5116.28 (9)
S—O2—Ca144.39 (5)C4—C5—H5A109.5
S—O3—Cavi170.63 (5)C4—C5—H5B109.5
C4—O4—Cavii132.62 (7)H5A—C5—H5B109.5
C4—N—C3123.86 (9)C4—C5—H5C109.5
C4—N—H1N118.1H5A—C5—H5C109.5
C3—N—H1N118.1H5B—C5—H5C109.5
O1—S—O2—Ca−156.68 (7)O2—S—C1—C2172.54 (8)
O3—S—O2—Ca−28.97 (9)S—C1—C2—C3−179.41 (8)
C1—S—O2—Ca86.85 (8)C4—N—C3—C2176.87 (11)
O3i—Ca—O2—S23.48 (8)C1—C2—C3—N170.74 (9)
O3ii—Ca—O2—S−156.52 (8)Cavii—O4—C4—N−169.56 (8)
O4iv—Ca—O2—S−68.73 (8)Cavii—O4—C4—C59.90 (18)
O4v—Ca—O2—S111.27 (8)C3—N—C4—O4−3.33 (19)
O1—S—C1—C252.32 (9)C3—N—C4—C5177.18 (11)
O3—S—C1—C2−68.44 (9)
Symmetry codes: (i) −x+1, −y+1, −z; (ii) x+1, y, z; (iii) −x+2, −y+1, −z; (iv) −x+1, −y, −z+1; (v) x+1, y+1, z−1; (vi) x−1, y, z; (vii) x−1, y−1, z+1.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N—H1N···O1viii0.862.153.0025 (12)169
C5—H5C···O1viii0.962.483.3569 (15)152
C1—H1B···O1ix0.972.533.3007 (14)137
Symmetry codes: (viii) −x, −y+1, −z+1; (ix) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula[Ca(C5H10NO4S)2]
Mr400.48
Crystal system, space groupTriclinic, P1
Temperature (K)293
a, b, c (Å)5.5372 (4), 8.1487 (6), 9.7578 (7)
α, β, γ (°)69.159 (1), 84.305 (2), 89.329 (2)
V (Å3)409.31 (5)
Z1
Radiation typeMo Kα
µ (mm−1)0.68
Crystal size (mm)0.29 × 0.23 × 0.08
Data collection
DiffractometerBruker SMART APEX CCD
Absorption correctionMulti-scan
(TWINABS; Bruker, 2008)
Tmin, Tmax0.827, 0.948
No. of measured, independent and
observed [I > 2σ(I)] reflections		22542, 8721, 7647
Rint0.027
(sin θ/λ)max (Å−1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.088, 1.02
No. of reflections8721
No. of parameters109
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.39, −0.33

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), SHELXTL/NT (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N—H1N···O1i0.862.153.0025 (12)168.6
C5—H5C···O1i0.962.483.3569 (15)152.2
C1—H1B···O1ii0.972.533.3007 (14)136.5
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1.
 

Acknowledgements

Samples of the title compound were kindly provided by Laboratorio Chimico Inter­nazionale SpA (Via T. Salvini 10, I-20122 Milan, Italy).

References

First citationAllen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19.  CSD CrossRef Web of Science Google Scholar
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 First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationToffoli, P., Rodier, N., Ceolin, R., Ladure, P. & Tran, G. (1988). Acta Cryst. C44, 1493–1494.  CSD CrossRef CAS Web of Science IUCr Journals Google Scholar

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ISSN: 2056-9890
Volume 67| Part 12| December 2011| Pages m1736-m1737
https://doi.org/10.1107/S1600536811046940
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