Poly[bis­(μ3-dodecyl sulfato)­calcium]

Sakane, G.; Tomohara, M.; Katayama, Y.; Hayashi, K.

doi:10.1107/S1600536810020659

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page m749

doi:10.1107/S1600536810020659

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Poly[bis(μ₃-dodecyl sulfato)calcium]

Genta Sakane,^a ^* Masahiro Tomohara,^a Yasuhiro Katayama ^a and Koya Hayashi ^a

^aDepartment of Chemistry, Okayama University of Science, Ridai-cho, Okayama 700-0005, Japan
^*Correspondence e-mail: gsakane@chem.ous.ac.jp

(Received 20 May 2010; accepted 31 May 2010; online 5 June 2010)

In the title compound [Ca(C₁₂H₂₅O₄S)₂]_n, the unique Ca^II ion lies on an inversion center and is coordinated in a slightly distorted octahedral environment by six O atoms from dodecyl sulfate anions. The crystal structure is based on hydrocarbon (dodecyl sulfate) layers which sandwich the Ca^II ions. Within the layers, the hydrocarbon zigzag chains are parallel to one another and interact via van der Waals forces.

Related literature

For studies of the title compound using atomic force microscopy, see: Rodriguez et al. (2002 ). For the Krafft point of the title compound, see: Hato & Shinoda (1973 ).

Experimental

Crystal data

[Ca(C₁₂H₂₅O₄S)₂]
M_r = 570.84
Triclinic, $[P \overline 1]$
a = 5.3888 (3) Å
b = 5.3834 (3) Å
c = 29.1922 (16) Å
α = 93.4321 (19)°
β = 90.099 (4)°
γ = 118.393 (5)°
V = 743.22 (7) Å³
Z = 1
Mo Kα radiation
μ = 0.39 mm⁻¹
T = 93 K
0.50 × 0.10 × 0.10 mm

Data collection

Rigaku R-AXIS IV diffractometer
4361 measured reflections
2500 independent reflections
2396 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.088
S = 1.08
2500 reflections
235 parameters
All H-atom parameters refined
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Data collection: PROCESS-AUTO (Rigaku, 1998 ); cell refinement: PROCESS-AUTO; data reduction: Yadokari-XG 2009 (Kabuto et al., 2009 ); program(s) used to solve structure: SIR2004 (Burla et al., 2005 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: Yadokari-XG 2009 and VESTA (Momma et al., 2008 ); software used to prepare material for publication: Yadokari-XG 2009.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810020659/lh5055sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810020659/lh5055Isup2.hkl

checkCIF report

Comment top

The crystal of the title compound, (I) (Fig. 1), is mechanically flexible because (I) is a two-dimensional layered compound which is characterized by strong covalent bonds and coordination bonds within the layers and weak van der Waals forces between the layers (Fig. 2).

Related literature top

For the atomic force microscopy of the title compound, see: Rodriguez et al. (2002). For the krafft point of the title compound, see: Hato et al. (1973).

Experimental top

The title compound was prepared by the addition of CaCl₂ to sodium dodecyl sulfate (SDS) in a water-ethanol mixed solvent. A crystal suitable for single-crystal X-ray diffraction was selected directly from the prepared sample.

Computing details top

Data collection: PROCESS-AUTO (Rigaku, 1998); cell refinement: PROCESS-AUTO (Rigaku, 1998); data reduction: Yadokari-XG 2009 (Kabuto et al., 2009); program(s) used to solve structure: SIR2004 (Burla et al., 2005); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Yadokari-XG 2009 (Kabuto et al., 2009) and VESTA (Momma et al., 2008); software used to prepare material for publication: Yadokari-XG 2009.

Figures top

	Fig. 1. The asymmetric unit of (I) with atom labels and 50% probability displacement ellipsoids for non-H atoms. H atoms are shown as spheres of arbitary radius.
	Fig. 2. The packing of (I), viewed along the b axis, showing hydrocarbon (dodecyl sulfate) layers which sandwich Ca atoms.

Poly[bis(µ₃-dodecyl sulfato)calcium] top

Crystal data top

[Ca(C₁₂H₂₅O₄S)₂]	Z = 1
M_r = 570.84	F(000) = 310
Triclinic, P1	D_x = 1.275 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71069 Å
a = 5.3888 (3) Å	Cell parameters from 3581 reflections
b = 5.3834 (3) Å	θ = 1.4–25.5°
c = 29.1922 (16) Å	µ = 0.39 mm⁻¹
α = 93.4321 (19)°	T = 93 K
β = 90.099 (4)°	Needle, colourless
γ = 118.393 (5)°	0.50 × 0.10 × 0.10 mm
V = 743.22 (7) Å³

Data collection top

Rigaku R-AXIS IV diffractometer	2396 reflections with I > 2σ(I)
Radiation source: rotating-anode X-ray	R_int = 0.031
Graphite Monochromator monochromator	θ_max = 25.5°, θ_min = 1.4°
Detector resolution: 10.0 pixels mm^-1	h = −5→5
ω scans	k = −6→6
4361 measured reflections	l = −35→35
2500 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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.088	All H-atom parameters refined
S = 1.08	w = 1/[σ²(F_o²) + (0.0512P)² + 0.4436P] where P = (F_o² + 2F_c²)/3
2500 reflections	(Δ/σ)_max = 0.001
235 parameters	Δρ_max = 0.39 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

[Ca(C₁₂H₂₅O₄S)₂]	γ = 118.393 (5)°
M_r = 570.84	V = 743.22 (7) Å³
Triclinic, P1	Z = 1
a = 5.3888 (3) Å	Mo Kα radiation
b = 5.3834 (3) Å	µ = 0.39 mm⁻¹
c = 29.1922 (16) Å	T = 93 K
α = 93.4321 (19)°	0.50 × 0.10 × 0.10 mm
β = 90.099 (4)°

Data collection top

Rigaku R-AXIS IV diffractometer	2396 reflections with I > 2σ(I)
4361 measured reflections	R_int = 0.031
2500 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.088	All H-atom parameters refined
S = 1.08	Δρ_max = 0.39 e Å⁻³
2500 reflections	Δρ_min = −0.43 e Å⁻³
235 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	−1.0000	−0.5000	0.5000	0.00470 (14)
S1	−0.37678 (7)	−0.17886 (7)	0.442177 (11)	0.00452 (13)
O1	−0.2874 (2)	−0.2127 (2)	0.39188 (3)	0.0088 (3)
O2	−0.6786 (2)	−0.3652 (2)	0.44018 (3)	0.0082 (2)
O3	−0.3024 (2)	0.1177 (2)	0.45120 (3)	0.0086 (2)
O4	−0.2238 (2)	−0.2644 (2)	0.47274 (3)	0.0106 (3)
C1	0.0057 (3)	−0.0139 (3)	0.38163 (5)	0.0099 (3)
C2	0.0898 (3)	−0.1473 (3)	0.34179 (5)	0.0098 (3)
C3	0.3718 (4)	0.0621 (3)	0.32332 (5)	0.0106 (3)
C4	0.4633 (4)	−0.0705 (3)	0.28353 (5)	0.0110 (3)
C5	0.7364 (4)	0.1365 (3)	0.26211 (5)	0.0108 (3)
C6	0.8242 (4)	0.0010 (3)	0.22225 (5)	0.0113 (3)
C7	1.0951 (4)	0.2073 (3)	0.20023 (5)	0.0121 (3)
C8	1.1836 (4)	0.0689 (3)	0.16093 (5)	0.0121 (3)
C9	1.4510 (4)	0.2760 (4)	0.13817 (5)	0.0135 (4)
C10	1.5462 (4)	0.1376 (4)	0.09979 (5)	0.0141 (4)
C11	1.8122 (4)	0.3468 (4)	0.07713 (6)	0.0202 (4)
C12	1.9121 (5)	0.2066 (5)	0.03986 (6)	0.0248 (4)
H1	−0.004 (5)	0.149 (5)	0.3738 (8)	0.030*
H2	0.129 (5)	0.029 (5)	0.4080 (8)	0.030*
H3	−0.066 (5)	−0.220 (5)	0.3174 (8)	0.030*
H4	0.095 (5)	−0.318 (5)	0.3516 (8)	0.030*
H5	0.352 (5)	0.218 (5)	0.3138 (8)	0.030*
H6	0.512 (5)	0.139 (5)	0.3479 (8)	0.030*
H7	0.302 (5)	−0.159 (5)	0.2590 (8)	0.030*
H8	0.484 (5)	−0.230 (5)	0.2944 (8)	0.030*
H9	0.708 (5)	0.296 (5)	0.2513 (7)	0.030*
H10	0.886 (5)	0.224 (5)	0.2861 (8)	0.030*
H11	0.670 (5)	−0.078 (5)	0.1986 (8)	0.030*
H12	0.850 (5)	−0.157 (5)	0.2328 (8)	0.030*
H13	1.065 (5)	0.367 (5)	0.1885 (8)	0.030*
H14	1.251 (5)	0.302 (5)	0.2243 (8)	0.030*
H15	1.032 (5)	−0.013 (5)	0.1384 (8)	0.030*
H16	1.216 (5)	−0.082 (5)	0.1722 (8)	0.030*
H17	1.415 (5)	0.426 (5)	0.1260 (8)	0.030*
H18	1.606 (5)	0.369 (5)	0.1619 (8)	0.030*
H19	1.399 (5)	0.041 (5)	0.0767 (8)	0.030*
H20	1.580 (5)	−0.007 (5)	0.1123 (8)	0.030*
H21	1.773 (5)	0.488 (5)	0.0641 (8)	0.030*
H22	1.955 (5)	0.437 (5)	0.1011 (8)	0.030*
H23	1.771 (6)	0.110 (5)	0.0152 (9)	0.037*
H24	1.940 (6)	0.050 (5)	0.0518 (8)	0.037*
H25	2.097 (6)	0.344 (5)	0.0273 (8)	0.037*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ca1	0.0033 (2)	0.0043 (2)	0.0060 (2)	0.00128 (17)	0.00087 (15)	0.00124 (15)
S1	0.0037 (2)	0.0044 (2)	0.00495 (19)	0.00141 (16)	0.00119 (13)	0.00066 (13)
O1	0.0050 (6)	0.0096 (6)	0.0069 (5)	−0.0003 (4)	0.0035 (4)	−0.0005 (4)
O2	0.0053 (6)	0.0081 (5)	0.0079 (5)	0.0005 (4)	0.0019 (4)	0.0005 (4)
O3	0.0090 (6)	0.0064 (5)	0.0099 (5)	0.0034 (4)	0.0004 (4)	−0.0006 (4)
O4	0.0099 (6)	0.0116 (5)	0.0120 (5)	0.0061 (5)	−0.0008 (4)	0.0036 (4)
C1	0.0061 (8)	0.0096 (8)	0.0106 (7)	0.0008 (6)	0.0044 (6)	0.0015 (6)
C2	0.0083 (8)	0.0110 (8)	0.0091 (7)	0.0039 (6)	0.0033 (6)	0.0005 (6)
C3	0.0091 (9)	0.0122 (8)	0.0099 (7)	0.0045 (6)	0.0036 (6)	0.0023 (6)
C4	0.0096 (8)	0.0130 (8)	0.0107 (7)	0.0057 (6)	0.0037 (6)	0.0015 (6)
C5	0.0094 (9)	0.0127 (8)	0.0103 (7)	0.0051 (7)	0.0043 (6)	0.0026 (6)
C6	0.0096 (9)	0.0149 (8)	0.0106 (7)	0.0066 (7)	0.0033 (6)	0.0019 (6)
C7	0.0094 (8)	0.0145 (8)	0.0116 (7)	0.0050 (7)	0.0050 (6)	0.0016 (6)
C8	0.0110 (9)	0.0150 (8)	0.0110 (7)	0.0066 (7)	0.0038 (6)	0.0019 (6)
C9	0.0117 (9)	0.0168 (9)	0.0128 (7)	0.0075 (7)	0.0064 (6)	0.0024 (6)
C10	0.0130 (9)	0.0187 (9)	0.0119 (7)	0.0087 (7)	0.0042 (6)	0.0009 (6)
C11	0.0215 (10)	0.0244 (10)	0.0181 (8)	0.0131 (8)	0.0113 (7)	0.0060 (7)
C12	0.0256 (11)	0.0392 (12)	0.0179 (9)	0.0216 (9)	0.0116 (7)	0.0067 (8)

Geometric parameters (Å, º) top

Ca1—O4ⁱ	2.2955 (11)	C4—H8	0.99 (2)
Ca1—O4ⁱⁱ	2.2956 (11)	C5—C6	1.529 (2)
Ca1—O3ⁱⁱⁱ	2.3177 (10)	C5—H9	1.01 (2)
Ca1—O3^iv	2.3178 (11)	C5—H10	0.98 (2)
Ca1—O2	2.3544 (10)	C6—C7	1.524 (2)
Ca1—O2^v	2.3544 (10)	C6—H11	0.99 (2)
Ca1—S1^v	3.4589 (4)	C6—H12	0.99 (2)
Ca1—S1	3.4589 (4)	C7—C8	1.528 (2)
S1—O4	1.4474 (11)	C7—H13	1.03 (2)
S1—O2	1.4476 (11)	C7—H14	1.00 (2)
S1—O3	1.4558 (11)	C8—C9	1.525 (2)
S1—O1	1.5732 (10)	C8—H15	0.96 (2)
O1—C1	1.4703 (18)	C8—H16	0.98 (2)
O3—Ca1^vi	2.3177 (10)	C9—C10	1.530 (2)
O4—Ca1^vii	2.2956 (11)	C9—H17	1.00 (2)
C1—C2	1.512 (2)	C9—H18	0.99 (2)
C1—H1	0.94 (2)	C10—C11	1.522 (2)
C1—H2	0.96 (2)	C10—H19	0.96 (2)
C2—C3	1.522 (2)	C10—H20	0.97 (2)
C2—H3	1.01 (2)	C11—C12	1.528 (2)
C2—H4	0.99 (2)	C11—H21	0.98 (2)
C3—C4	1.529 (2)	C11—H22	0.96 (2)
C3—H5	0.95 (2)	C12—H23	0.97 (3)
C3—H6	0.96 (2)	C12—H24	1.00 (3)
C4—C5	1.525 (2)	C12—H25	1.00 (3)
C4—H7	1.03 (2)

O4ⁱ—Ca1—O4ⁱⁱ	179.997 (1)	C2—C3—H6	109.6 (14)
O4ⁱ—Ca1—O3ⁱⁱⁱ	86.81 (4)	C4—C3—H6	111.4 (15)
O4ⁱⁱ—Ca1—O3ⁱⁱⁱ	93.19 (4)	H5—C3—H6	105.4 (19)
O4ⁱ—Ca1—O3^iv	93.19 (4)	C5—C4—C3	114.00 (13)
O4ⁱⁱ—Ca1—O3^iv	86.81 (4)	C5—C4—H7	110.0 (13)
O3ⁱⁱⁱ—Ca1—O3^iv	179.997 (1)	C3—C4—H7	108.4 (14)
O4ⁱ—Ca1—O2	92.58 (4)	C5—C4—H8	109.4 (14)
O4ⁱⁱ—Ca1—O2	87.43 (4)	C3—C4—H8	109.1 (13)
O3ⁱⁱⁱ—Ca1—O2	87.11 (4)	H7—C4—H8	105.6 (19)
O3^iv—Ca1—O2	92.90 (4)	C4—C5—C6	113.36 (13)
O4ⁱ—Ca1—O2^v	87.43 (4)	C4—C5—H9	107.5 (14)
O4ⁱⁱ—Ca1—O2^v	92.57 (4)	C6—C5—H9	110.2 (13)
O3ⁱⁱⁱ—Ca1—O2^v	92.89 (4)	C4—C5—H10	109.0 (14)
O3^iv—Ca1—O2^v	87.10 (4)	C6—C5—H10	111.1 (15)
O2—Ca1—O2^v	179.998 (2)	H9—C5—H10	105.3 (19)
O4ⁱ—Ca1—S1^v	80.30 (3)	C7—C6—C5	113.72 (13)
O4ⁱⁱ—Ca1—S1^v	99.70 (3)	C7—C6—H11	108.4 (13)
O3ⁱⁱⁱ—Ca1—S1^v	75.13 (3)	C5—C6—H11	107.9 (14)
O3^iv—Ca1—S1^v	104.86 (3)	C7—C6—H12	108.5 (14)
O2—Ca1—S1^v	161.13 (3)	C5—C6—H12	110.0 (13)
O2^v—Ca1—S1^v	18.87 (3)	H11—C6—H12	108.1 (19)
O4ⁱ—Ca1—S1	99.70 (3)	C6—C7—C8	113.32 (13)
O4ⁱⁱ—Ca1—S1	80.30 (3)	C6—C7—H13	108.1 (14)
O3ⁱⁱⁱ—Ca1—S1	104.86 (3)	C8—C7—H13	109.9 (13)
O3^iv—Ca1—S1	75.14 (3)	C6—C7—H14	109.6 (13)
O2—Ca1—S1	18.87 (3)	C8—C7—H14	110.4 (14)
O2^v—Ca1—S1	161.13 (3)	H13—C7—H14	105.1 (18)
S1^v—Ca1—S1	180.0	C9—C8—C7	113.44 (13)
O4—S1—O2	113.59 (6)	C9—C8—H15	108.9 (14)
O4—S1—O3	111.92 (6)	C7—C8—H15	107.6 (15)
O2—S1—O3	112.94 (6)	C9—C8—H16	108.1 (15)
O4—S1—O1	107.44 (6)	C7—C8—H16	110.0 (13)
O2—S1—O1	103.17 (6)	H15—C8—H16	108.7 (19)
O3—S1—O1	107.04 (6)	C8—C9—C10	113.78 (14)
O4—S1—Ca1	94.37 (5)	C8—C9—H17	107.8 (14)
O2—S1—Ca1	31.74 (4)	C10—C9—H17	110.3 (13)
O3—S1—Ca1	100.49 (5)	C8—C9—H18	108.8 (13)
O1—S1—Ca1	134.58 (4)	C10—C9—H18	108.4 (14)
C1—O1—S1	115.39 (9)	H17—C9—H18	107.7 (18)
S1—O2—Ca1	129.39 (6)	C11—C10—C9	113.27 (14)
S1—O3—Ca1^vi	138.18 (7)	C11—C10—H19	108.9 (14)
S1—O4—Ca1^vii	160.70 (7)	C9—C10—H19	110.8 (15)
O1—C1—C2	107.53 (12)	C11—C10—H20	109.1 (15)
O1—C1—H1	103.4 (15)	C9—C10—H20	108.9 (14)
C2—C1—H1	112.3 (14)	H19—C10—H20	105.6 (19)
O1—C1—H2	111.0 (14)	C10—C11—C12	113.14 (16)
C2—C1—H2	111.6 (15)	C10—C11—H21	107.9 (15)
H1—C1—H2	111 (2)	C12—C11—H21	110.1 (13)
C1—C2—C3	111.44 (13)	C10—C11—H22	106.5 (14)
C1—C2—H3	107.7 (14)	C12—C11—H22	109.9 (15)
C3—C2—H3	111.5 (13)	H21—C11—H22	109.1 (19)
C1—C2—H4	109.4 (13)	C11—C12—H23	112.2 (16)
C3—C2—H4	111.2 (14)	C11—C12—H24	111.7 (14)
H3—C2—H4	105.3 (19)	H23—C12—H24	103 (2)
C2—C3—C4	112.23 (13)	C11—C12—H25	112.3 (14)
C2—C3—H5	107.4 (15)	H23—C12—H25	111 (2)
C4—C3—H5	110.6 (14)	H24—C12—H25	107 (2)

O4ⁱ—Ca1—S1—O4	161.30 (7)	Ca1—S1—O1—C1	176.64 (8)
O4ⁱⁱ—Ca1—S1—O4	−18.69 (7)	O4—S1—O2—Ca1	56.79 (10)
O3ⁱⁱⁱ—Ca1—S1—O4	−109.44 (5)	O3—S1—O2—Ca1	−72.04 (9)
O3^iv—Ca1—S1—O4	70.56 (5)	O1—S1—O2—Ca1	172.76 (7)
O2—Ca1—S1—O4	−129.73 (10)	O4ⁱ—Ca1—O2—S1	112.94 (8)
O2^v—Ca1—S1—O4	50.26 (10)	O4ⁱⁱ—Ca1—O2—S1	−67.06 (8)
S1^v—Ca1—S1—O4	−136 (16)	O3ⁱⁱⁱ—Ca1—O2—S1	−160.39 (9)
O4ⁱ—Ca1—S1—O2	−68.96 (9)	O3^iv—Ca1—O2—S1	19.61 (9)
O4ⁱⁱ—Ca1—S1—O2	111.04 (9)	O2^v—Ca1—O2—S1	−17 (11)
O3ⁱⁱⁱ—Ca1—S1—O2	20.30 (9)	S1^v—Ca1—O2—S1	180.0
O3^iv—Ca1—S1—O2	−159.71 (9)	O4—S1—O3—Ca1^vi	1.53 (12)
O2^v—Ca1—S1—O2	179.998 (2)	O2—S1—O3—Ca1^vi	131.22 (9)
S1^v—Ca1—S1—O2	−6 (16)	O1—S1—O3—Ca1^vi	−115.93 (9)
O4ⁱ—Ca1—S1—O3	48.05 (5)	Ca1—S1—O3—Ca1^vi	100.63 (9)
O4ⁱⁱ—Ca1—S1—O3	−131.95 (5)	O2—S1—O4—Ca1^vii	80.8 (2)
O3ⁱⁱⁱ—Ca1—S1—O3	137.31 (7)	O3—S1—O4—Ca1^vii	−149.8 (2)
O3^iv—Ca1—S1—O3	−42.70 (7)	O1—S1—O4—Ca1^vii	−32.6 (2)
O2—Ca1—S1—O3	117.01 (9)	Ca1—S1—O4—Ca1^vii	107.0 (2)
O2^v—Ca1—S1—O3	−62.99 (9)	S1—O1—C1—C2	156.54 (11)
S1^v—Ca1—S1—O3	111 (16)	O1—C1—C2—C3	170.34 (13)
O4ⁱ—Ca1—S1—O1	−78.87 (7)	C1—C2—C3—C4	178.97 (14)
O4ⁱⁱ—Ca1—S1—O1	101.13 (7)	C2—C3—C4—C5	176.61 (13)
O3ⁱⁱⁱ—Ca1—S1—O1	10.38 (7)	C3—C4—C5—C6	−179.75 (13)
O3^iv—Ca1—S1—O1	−169.62 (7)	C4—C5—C6—C7	179.24 (13)
O2—Ca1—S1—O1	−9.91 (10)	C5—C6—C7—C8	179.09 (13)
O2^v—Ca1—S1—O1	170.08 (10)	C6—C7—C8—C9	178.78 (14)
S1^v—Ca1—S1—O1	−16 (16)	C7—C8—C9—C10	178.20 (14)
O4—S1—O1—C1	−68.41 (11)	C8—C9—C10—C11	179.60 (15)
O2—S1—O1—C1	171.31 (11)	C9—C10—C11—C12	178.15 (15)
O3—S1—O1—C1	51.95 (12)

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

Experimental details

Crystal data
Chemical formula	[Ca(C₁₂H₂₅O₄S)₂]
M_r	570.84
Crystal system, space group	Triclinic, P1
Temperature (K)	93
a, b, c (Å)	5.3888 (3), 5.3834 (3), 29.1922 (16)
α, β, γ (°)	93.4321 (19), 90.099 (4), 118.393 (5)
V (Å³)	743.22 (7)
Z	1
Radiation type	Mo Kα
µ (mm⁻¹)	0.39
Crystal size (mm)	0.50 × 0.10 × 0.10

Data collection
Diffractometer	Rigaku R-AXIS IV diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	4361, 2500, 2396
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.088, 1.08
No. of reflections	2500
No. of parameters	235
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.43

Computer programs: PROCESS-AUTO (Rigaku, 1998), SIR2004 (Burla et al., 2005), SHELXL97 (Sheldrick, 2008), Yadokari-XG 2009 (Kabuto et al., 2009) and VESTA (Momma et al., 2008), Yadokari-XG 2009.

Acknowledgements

This work was supported by matching fund subsidy for private universities from MEXT (Ministry of Education, Culture, Sports, Science and Technology, Japan).

References

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