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Acta Cryst. (2007). E63, m1935    [ doi:10.1107/S1600536807029327 ]

Diaquabis[4-methyl-2-(4-methylphenylsulfonamido)pentanoato-[kappa]O]calcium(II)

X.-S. Tai, J. Yin and M.-Y. Hao

Abstract top

In the title compound, [Ca(C13H18NO4S)2(H2O)2], a distorted CaO4 tetrahedron arises from the coordination of the two ligands and two water molecules. A network of hydrogen bonds helps to establish the crystal packing.

Comment top

As part of our ongoing studies of metal coordination complexes with multidentate ligands (Tai et al., 2005), the synthesis and structure of the title compound, (I), is reported.

Two O-monodentate ligands and two water molecules are attached to the calcium atom, resulting in a distorted CaO4 tetrahedron (Fig. 1). The identical S2=O8 [1.437 (3) Å], S2=O7 [1.430 (3) Å], C14=O6 [1.243 (5) Å] and S1=O3 [1.427 (3) Å], S1=O4 [1.423 (3) Å], C1=O2 [1.254 (5) Å] bonds lengths imply double bond character. The dihedral angle between the two benzene ring mean planes (C7—C12 and C20—C25) is 129.9 (3) °.

Two molecules of water complete the structure of (I) and a network of hydrogen bonds helps to establish the crystal packing.

Related literature top

For related literature, see: Tai et al. (2005).

Experimental top

1 mmol of calcium perchlorate was added to a solution of 4-toluenesulfonyl chloride-L-leucine (2 mmol) in 10 ml of CH3OH/H2O (v/v 1:1). The mixture was continuously stirred for 4 h at refluxing temperature, evaporating some methanol, then, upon cooling, the solid product was collected by filtration and dried in vacuo (yield 69%). Clear blocks of (I) were obtained by evaporation from a methanol solution after a week.

Refinement top

The water H atoms were located in a difference map and refined as riding in their as-found relative positions with Uiso(H) = 1.2Ueq(O). Other H atoms were placed geometrically (C—H = 0.93–0.97 Å, O—H = 0.82 Å, N—H = 0.86 Å) and refined as riding with Uiso(H) = 1.2Ueq(C,N) or 1.5Ueq(O).

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SMART; data reduction: SAINT (Bruker, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1997); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. The complex molecule in (I) with 50% probabiility ellipsoids (arbitrary spheres for the H atoms).
Diaquabis[4-methyl-2-(4-methylphenylsulfonamido)pentanoato-κO]calcium(II) top
Crystal data top
[Ca(C13H18NO4S)2(H2O)2]Dx = 1.356 Mg m−3
Mr = 644.80Mo Kα radiation
λ = 0.71073 Å
Orthorhombic, P212121Cell parameters from 4003 reflections
a = 5.1575 (11) Åθ = 2.3–23.3º
b = 17.430 (2) ŵ = 0.39 mm−1
c = 35.147 (4) ÅT = 298 (2) K
V = 3159.5 (8) Å3Colourless, block
Z = 40.58 × 0.40 × 0.38 mm
F000 = 1368
Data collection top
Bruker CCD area-detector
diffractometer		5549 independent reflections
Radiation source: fine-focus sealed tube4532 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.048
T = 298(2) Kθmax = 25.0º
φ and ω scansθmin = 1.3º
Absorption correction: multi-scan
(SADABS; Bruker, 1997)		h = −6→6
Tmin = 0.808, Tmax = 0.868k = −20→14
14074 measured reflectionsl = −39→41
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.051  w = 1/[σ2(Fo2) + (0.0424P)2 + 1.9751P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.112(Δ/σ)max < 0.001
S = 1.02Δρmax = 0.26 e Å−3
5549 reflectionsΔρmin = −0.28 e Å−3
370 parametersExtinction correction: none
90 restraintsAbsolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.04 (5)
Secondary atom site location: difference Fourier map
Crystal data top
[Ca(C13H18NO4S)2(H2O)2]V = 3159.5 (8) Å3
Mr = 644.80Z = 4
Orthorhombic, P212121Mo Kα
a = 5.1575 (11) ŵ = 0.39 mm−1
b = 17.430 (2) ÅT = 298 (2) K
c = 35.147 (4) Å0.58 × 0.40 × 0.38 mm
Data collection top
Bruker CCD area-detector
diffractometer		5549 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 1997)		4532 reflections with I > 2σ(I)
Tmin = 0.808, Tmax = 0.868Rint = 0.048
14074 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.051H-atom parameters constrained
wR(F2) = 0.112Δρmax = 0.26 e Å−3
S = 1.02Δρmin = −0.28 e Å−3
5549 reflectionsAbsolute structure: Flack (1983)
370 parametersFlack parameter: 0.04 (5)
90 restraints
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
Ca10.85026 (15)0.64157 (4)0.06135 (2)0.02487 (19)
N11.6802 (6)0.46340 (18)0.13168 (10)0.0321 (8)
H11.76780.49250.11490.039*
N20.0086 (6)0.84341 (17)0.11043 (9)0.0298 (8)
H2−0.08640.80620.09940.036*
O11.0994 (5)0.56081 (16)0.09914 (8)0.0379 (8)
O21.5023 (6)0.56391 (15)0.07629 (8)0.0369 (7)
O31.9911 (6)0.36387 (18)0.11820 (10)0.0559 (9)
O41.5574 (6)0.32834 (17)0.14181 (10)0.0549 (10)
O50.5959 (5)0.73580 (15)0.09304 (8)0.0341 (7)
O60.2036 (5)0.72545 (15)0.06731 (8)0.0369 (7)
O70.1982 (6)0.91204 (16)0.05345 (7)0.0386 (7)
O8−0.2625 (5)0.92264 (17)0.06999 (8)0.0451 (8)
O90.6424 (8)0.69671 (18)0.00867 (8)0.0613 (10)
H9A0.49810.71030.01820.074*
H9B0.61400.6662−0.00970.074*
O101.0908 (6)0.57833 (18)0.01260 (9)0.0545 (9)
H10A1.06540.5833−0.01120.065*
H10B1.24490.57790.02110.065*
S11.7171 (2)0.37528 (6)0.11838 (4)0.0408 (3)
S20.0025 (2)0.91630 (6)0.08220 (3)0.0324 (3)
C11.3381 (8)0.5440 (2)0.10069 (11)0.0292 (9)
C21.4202 (8)0.4970 (2)0.13530 (11)0.0312 (10)
H2A1.29500.45530.13890.037*
C31.4144 (10)0.5481 (3)0.17045 (13)0.0488 (13)
H3A1.55020.58630.16810.059*
H3B1.24990.57510.17100.059*
C41.4492 (10)0.5064 (3)0.20805 (13)0.0532 (13)
H41.60390.47400.20580.064*
C51.2227 (13)0.4545 (5)0.21638 (18)0.106 (2)
H5A1.07010.48490.22050.159*
H5B1.25860.42480.23880.159*
H5C1.19490.42070.19520.159*
C61.4963 (17)0.5625 (4)0.24014 (17)0.100 (2)
H6A1.34820.59540.24290.150*
H6B1.64670.59290.23450.150*
H6C1.52370.53480.26340.150*
C71.6044 (9)0.3669 (2)0.07123 (13)0.0397 (11)
C81.3987 (9)0.3197 (2)0.06278 (15)0.0471 (12)
H81.32250.28990.08170.057*
C91.3070 (11)0.3169 (3)0.02595 (15)0.0544 (14)
H91.16700.28520.02050.065*
C101.4153 (9)0.3596 (3)−0.00300 (14)0.0487 (12)
C111.6259 (11)0.4066 (3)0.00626 (15)0.0527 (13)
H111.70400.4360−0.01260.063*
C121.7187 (9)0.4097 (2)0.04283 (14)0.0459 (12)
H121.85970.44090.04850.055*
C131.3128 (12)0.3565 (3)−0.04291 (15)0.0747 (17)
H13A1.15320.3282−0.04330.112*
H13B1.43720.3316−0.05910.112*
H13C1.28230.4077−0.05190.112*
C140.3589 (8)0.7525 (2)0.09079 (11)0.0287 (9)
C150.2574 (8)0.8097 (2)0.12076 (11)0.0311 (10)
H150.38510.85070.12410.037*
C160.2253 (10)0.7668 (3)0.15842 (13)0.0485 (12)
H16A0.09990.72590.15470.058*
H16B0.38960.74300.16480.058*
C170.1382 (12)0.8154 (3)0.19202 (13)0.0525 (12)
H17−0.02590.84000.18500.063*
C180.3295 (13)0.8783 (4)0.20161 (17)0.090 (2)
H18A0.35980.90930.17950.135*
H18B0.48980.85580.20980.135*
H18C0.26010.90970.22160.135*
C190.0868 (19)0.7650 (4)0.22628 (16)0.110 (3)
H19A0.24380.73920.23350.166*
H19B−0.04350.72770.22000.166*
H19C0.02750.79610.24710.166*
C200.0724 (8)0.9945 (2)0.11172 (12)0.0324 (10)
C210.2778 (9)1.0421 (2)0.10399 (13)0.0413 (11)
H210.39071.03100.08410.050*
C220.3151 (11)1.1071 (2)0.12623 (13)0.0494 (13)
H220.45371.13950.12100.059*
C230.1494 (11)1.1245 (2)0.15617 (13)0.0506 (13)
C24−0.0499 (11)1.0745 (3)0.16340 (14)0.0567 (15)
H24−0.16181.08460.18350.068*
C25−0.0886 (10)1.0103 (3)0.14186 (13)0.0492 (13)
H25−0.22440.97720.14760.059*
C260.1876 (14)1.1967 (3)0.17961 (16)0.081 (2)
H26A0.13321.24050.16510.121*
H26B0.36751.20190.18610.121*
H26C0.08621.19330.20250.121*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Ca10.0183 (4)0.0281 (4)0.0282 (4)−0.0003 (4)−0.0001 (4)0.0012 (3)
N10.0190 (19)0.0360 (18)0.041 (2)0.0032 (16)−0.0011 (17)0.0109 (15)
N20.0227 (18)0.0241 (17)0.043 (2)0.0018 (15)−0.0004 (18)−0.0088 (14)
O10.0176 (16)0.0478 (18)0.0483 (19)0.0029 (14)−0.0024 (13)0.0210 (14)
O20.0287 (16)0.0385 (17)0.0434 (17)−0.0011 (14)0.0052 (15)0.0130 (13)
O30.0298 (17)0.0490 (19)0.089 (3)0.0144 (17)−0.0061 (19)0.0041 (19)
O40.049 (2)0.0426 (18)0.073 (2)−0.0043 (16)−0.0045 (19)0.0275 (17)
O50.0152 (16)0.0380 (16)0.0493 (18)0.0023 (13)−0.0013 (13)−0.0079 (13)
O60.0211 (16)0.0387 (16)0.0509 (19)0.0002 (13)−0.0084 (14)−0.0155 (14)
O70.0358 (18)0.0503 (17)0.0296 (15)−0.0021 (15)0.0089 (14)−0.0053 (13)
O80.0283 (17)0.0517 (18)0.055 (2)0.0098 (15)−0.0129 (15)−0.0051 (16)
O90.076 (3)0.075 (2)0.0337 (18)0.022 (2)−0.0120 (19)0.0049 (16)
O100.044 (2)0.077 (2)0.0420 (18)0.0081 (19)0.0030 (16)−0.0154 (17)
S10.0280 (6)0.0339 (6)0.0606 (8)0.0043 (5)−0.0029 (6)0.0105 (5)
S20.0246 (5)0.0365 (6)0.0362 (6)0.0038 (5)−0.0019 (5)−0.0051 (5)
C10.023 (2)0.027 (2)0.037 (2)−0.003 (2)−0.003 (2)0.0047 (17)
C20.022 (2)0.037 (2)0.035 (2)0.0023 (19)0.0007 (19)0.0125 (19)
C30.045 (3)0.054 (3)0.048 (3)0.017 (2)−0.002 (2)0.006 (2)
C40.045 (3)0.073 (3)0.041 (3)0.013 (3)−0.004 (2)0.008 (2)
C50.077 (5)0.171 (6)0.070 (4)−0.023 (5)−0.002 (4)0.050 (4)
C60.130 (6)0.111 (5)0.059 (4)0.029 (5)−0.010 (4)−0.013 (4)
C70.033 (2)0.030 (2)0.056 (3)0.004 (2)0.005 (2)0.003 (2)
C80.044 (3)0.040 (3)0.058 (3)0.001 (2)0.010 (3)0.002 (2)
C90.047 (4)0.044 (3)0.073 (4)−0.008 (3)0.000 (3)−0.007 (3)
C100.045 (3)0.044 (3)0.058 (3)0.003 (3)−0.007 (3)−0.002 (3)
C110.052 (3)0.045 (3)0.061 (3)−0.003 (3)0.008 (3)0.009 (2)
C120.037 (3)0.036 (2)0.065 (3)−0.007 (2)−0.002 (3)0.006 (2)
C130.079 (5)0.075 (4)0.069 (4)−0.007 (4)−0.010 (3)−0.004 (3)
C140.021 (2)0.026 (2)0.039 (2)−0.0007 (19)0.002 (2)0.0000 (18)
C150.030 (2)0.029 (2)0.034 (2)0.0027 (18)−0.002 (2)−0.0069 (18)
C160.051 (3)0.047 (3)0.047 (3)0.012 (2)0.006 (2)0.004 (2)
C170.058 (3)0.058 (3)0.041 (3)0.010 (3)0.011 (3)0.002 (2)
C180.096 (5)0.104 (4)0.070 (4)0.007 (4)−0.001 (4)−0.037 (3)
C190.170 (7)0.101 (5)0.060 (4)0.024 (5)0.042 (4)0.023 (3)
C200.026 (2)0.032 (2)0.039 (2)0.0051 (19)−0.002 (2)0.0017 (19)
C210.039 (3)0.040 (2)0.044 (3)−0.004 (2)0.007 (2)−0.001 (2)
C220.057 (3)0.041 (3)0.050 (3)−0.015 (3)−0.001 (3)0.001 (2)
C230.066 (4)0.034 (2)0.052 (3)−0.008 (3)0.005 (3)−0.002 (2)
C240.069 (4)0.052 (3)0.049 (3)−0.010 (3)0.022 (3)−0.013 (3)
C250.051 (3)0.043 (3)0.054 (3)−0.010 (2)0.023 (3)−0.005 (2)
C260.125 (6)0.045 (3)0.072 (4)−0.007 (4)0.012 (4)−0.016 (3)
Geometric parameters (Å, °) top
Ca1—O2i2.308 (3)C6—H6C0.9600
Ca1—O12.323 (3)C7—C81.375 (6)
Ca1—O92.345 (3)C7—C121.378 (6)
Ca1—O6ii2.346 (3)C8—C91.379 (7)
Ca1—O52.379 (3)C8—H80.9300
Ca1—O102.385 (3)C9—C101.378 (7)
Ca1—H9A2.6516C9—H90.9300
Ca1—H10B2.7147C10—C111.399 (7)
N1—C21.469 (5)C10—C131.500 (7)
N1—S11.617 (3)C11—C121.372 (7)
N1—H10.9000C11—H110.9300
N2—C151.458 (5)C12—H120.9300
N2—S21.612 (3)C13—H13A0.9600
N2—H20.9000C13—H13B0.9600
O1—C11.267 (5)C13—H13C0.9600
O2—C11.254 (5)C14—C151.542 (5)
O2—Ca1ii2.308 (3)C15—C161.529 (6)
O3—S11.427 (3)C15—H150.9800
O4—S11.423 (3)C16—C171.521 (6)
O5—C141.259 (5)C16—H16A0.9700
O6—C141.243 (5)C16—H16B0.9700
O6—Ca1i2.346 (3)C17—C181.513 (8)
O7—S21.430 (3)C17—C191.514 (7)
O8—S21.437 (3)C17—H170.9800
O9—H9A0.8500C18—H18A0.9600
O9—H9B0.8499C18—H18B0.9600
O10—H10A0.8498C18—H18C0.9600
O10—H10B0.8498C19—H19A0.9600
S1—C71.762 (5)C19—H19B0.9600
S2—C201.750 (4)C19—H19C0.9600
C1—C21.526 (5)C20—C211.373 (6)
C2—C31.523 (6)C20—C251.374 (6)
C2—H2A0.9800C21—C221.389 (6)
C3—C41.519 (6)C21—H210.9300
C3—H3A0.9700C22—C231.389 (7)
C3—H3B0.9700C22—H220.9300
C4—C51.506 (8)C23—C241.371 (7)
C4—C61.512 (8)C23—C261.516 (6)
C4—H40.9800C24—C251.366 (6)
C5—H5A0.9600C24—H240.9300
C5—H5B0.9600C25—H250.9300
C5—H5C0.9600C26—H26A0.9600
C6—H6A0.9600C26—H26B0.9600
C6—H6B0.9600C26—H26C0.9600
O2i—Ca1—O186.82 (10)H6A—C6—H6B109.5
O2i—Ca1—O993.70 (12)C4—C6—H6C109.5
O1—Ca1—O9162.26 (12)H6A—C6—H6C109.5
O2i—Ca1—O6ii161.64 (11)H6B—C6—H6C109.5
O1—Ca1—O6ii84.08 (10)C8—C7—C12119.8 (4)
O9—Ca1—O6ii99.80 (12)C8—C7—S1120.5 (4)
O2i—Ca1—O582.51 (10)C12—C7—S1119.7 (4)
O1—Ca1—O5117.11 (11)C7—C8—C9119.2 (5)
O9—Ca1—O580.48 (11)C7—C8—H8120.4
O6ii—Ca1—O587.49 (9)C9—C8—H8120.4
O2i—Ca1—O10107.26 (11)C10—C9—C8122.4 (5)
O1—Ca1—O1080.97 (11)C10—C9—H9118.8
O9—Ca1—O1081.95 (12)C8—C9—H9118.8
O6ii—Ca1—O1087.03 (11)C9—C10—C11117.3 (5)
O5—Ca1—O10160.42 (11)C9—C10—C13121.9 (5)
O2i—Ca1—H9A82.1C11—C10—C13120.8 (5)
O1—Ca1—H9A168.4C12—C11—C10120.8 (5)
O9—Ca1—H9A18.3C12—C11—H11119.6
O6ii—Ca1—H9A107.6C10—C11—H11119.6
O5—Ca1—H9A65.0C11—C12—C7120.5 (4)
O10—Ca1—H9A98.9C11—C12—H12119.7
O2i—Ca1—H10B117.5C7—C12—H12119.7
O1—Ca1—H10B68.6C10—C13—H13A109.5
O9—Ca1—H10B95.7C10—C13—H13B109.5
O6ii—Ca1—H10B73.7H13A—C13—H13B109.5
O5—Ca1—H10B159.9C10—C13—H13C109.5
O10—Ca1—H10B17.7H13A—C13—H13C109.5
H9A—Ca1—H10B113.6H13B—C13—H13C109.5
C2—N1—S1120.7 (3)O6—C14—O5125.4 (4)
C2—N1—H1106.9O6—C14—C15118.7 (4)
S1—N1—H1106.7O5—C14—C15115.8 (4)
C15—N2—S2119.2 (3)N2—C15—C16108.5 (3)
C15—N2—H2107.2N2—C15—C14112.9 (3)
S2—N2—H2107.1C16—C15—C14108.2 (3)
C1—O1—Ca1134.6 (3)N2—C15—H15109.1
C1—O2—Ca1ii147.5 (3)C16—C15—H15109.1
C14—O5—Ca1131.7 (3)C14—C15—H15109.1
C14—O6—Ca1i142.8 (3)C17—C16—C15115.6 (4)
Ca1—O9—H9A101.7C17—C16—H16A108.4
Ca1—O9—H9B115.1C15—C16—H16A108.4
H9A—O9—H9B108.9C17—C16—H16B108.4
Ca1—O10—H10A125.3C15—C16—H16B108.4
Ca1—O10—H10B103.7H16A—C16—H16B107.5
H10A—O10—H10B119.5C18—C17—C19110.9 (5)
O4—S1—O3119.7 (2)C18—C17—C16112.6 (4)
O4—S1—N1108.1 (2)C19—C17—C16110.2 (4)
O3—S1—N1104.49 (19)C18—C17—H17107.6
O4—S1—C7107.8 (2)C19—C17—H17107.6
O3—S1—C7108.1 (2)C16—C17—H17107.6
N1—S1—C7108.15 (18)C17—C18—H18A109.5
O7—S2—O8117.66 (18)C17—C18—H18B109.5
O7—S2—N2112.35 (18)H18A—C18—H18B109.5
O8—S2—N2105.22 (19)C17—C18—H18C109.5
O7—S2—C20108.30 (19)H18A—C18—H18C109.5
O8—S2—C20108.24 (19)H18B—C18—H18C109.5
N2—S2—C20104.17 (18)C17—C19—H19A109.5
O2—C1—O1124.2 (4)C17—C19—H19B109.5
O2—C1—C2120.4 (4)H19A—C19—H19B109.5
O1—C1—C2115.3 (4)C17—C19—H19C109.5
N1—C2—C3108.7 (3)H19A—C19—H19C109.5
N1—C2—C1113.5 (3)H19B—C19—H19C109.5
C3—C2—C1109.1 (3)C21—C20—C25119.8 (4)
N1—C2—H2A108.5C21—C20—S2120.8 (3)
C3—C2—H2A108.5C25—C20—S2119.3 (3)
C1—C2—H2A108.5C20—C21—C22119.2 (4)
C4—C3—C2115.0 (4)C20—C21—H21120.4
C4—C3—H3A108.5C22—C21—H21120.4
C2—C3—H3A108.5C21—C22—C23121.3 (5)
C4—C3—H3B108.5C21—C22—H22119.3
C2—C3—H3B108.5C23—C22—H22119.3
H3A—C3—H3B107.5C24—C23—C22117.5 (4)
C5—C4—C6111.6 (5)C24—C23—C26121.6 (5)
C5—C4—C3111.4 (4)C22—C23—C26120.9 (5)
C6—C4—C3111.0 (5)C25—C24—C23121.8 (5)
C5—C4—H4107.6C25—C24—H24119.1
C6—C4—H4107.6C23—C24—H24119.1
C3—C4—H4107.6C24—C25—C20120.2 (4)
C4—C5—H5A109.5C24—C25—H25119.9
C4—C5—H5B109.5C20—C25—H25119.9
H5A—C5—H5B109.5C23—C26—H26A109.5
C4—C5—H5C109.5C23—C26—H26B109.5
H5A—C5—H5C109.5H26A—C26—H26B109.5
H5B—C5—H5C109.5C23—C26—H26C109.5
C4—C6—H6A109.5H26A—C26—H26C109.5
C4—C6—H6B109.5H26B—C26—H26C109.5
O2i—Ca1—O1—C1155.9 (4)C7—C8—C9—C100.5 (7)
O9—Ca1—O1—C163.7 (6)C8—C9—C10—C110.2 (7)
O6ii—Ca1—O1—C1−40.1 (4)C8—C9—C10—C13−179.6 (5)
O5—Ca1—O1—C1−124.2 (4)C9—C10—C11—C12−0.2 (7)
O10—Ca1—O1—C147.9 (4)C13—C10—C11—C12179.6 (5)
O2i—Ca1—O5—C14−45.5 (4)C10—C11—C12—C7−0.5 (7)
O1—Ca1—O5—C14−128.1 (3)C8—C7—C12—C111.2 (7)
O9—Ca1—O5—C1449.5 (4)S1—C7—C12—C11−177.0 (4)
O6ii—Ca1—O5—C14149.9 (4)Ca1i—O6—C14—O5108.2 (5)
O10—Ca1—O5—C1476.0 (5)Ca1i—O6—C14—C15−69.9 (5)
C2—N1—S1—O4−51.5 (4)Ca1—O5—C14—O6−7.3 (6)
C2—N1—S1—O3179.9 (3)Ca1—O5—C14—C15170.9 (2)
C2—N1—S1—C764.9 (4)S2—N2—C15—C16156.8 (3)
C15—N2—S2—O736.1 (3)S2—N2—C15—C14−83.2 (4)
C15—N2—S2—O8165.3 (3)O6—C14—C15—N2−18.4 (5)
C15—N2—S2—C20−80.9 (3)O5—C14—C15—N2163.3 (3)
Ca1ii—O2—C1—O1107.7 (5)O6—C14—C15—C16101.7 (4)
Ca1ii—O2—C1—C2−71.6 (6)O5—C14—C15—C16−76.6 (5)
Ca1—O1—C1—O2−9.3 (7)N2—C15—C16—C17−60.0 (5)
Ca1—O1—C1—C2170.0 (3)C14—C15—C16—C17177.2 (4)
S1—N1—C2—C3140.5 (3)C15—C16—C17—C18−61.5 (6)
S1—N1—C2—C1−97.9 (4)C15—C16—C17—C19174.1 (5)
O2—C1—C2—N1−14.3 (5)O7—S2—C20—C213.6 (4)
O1—C1—C2—N1166.3 (3)O8—S2—C20—C21−125.0 (4)
O2—C1—C2—C3107.1 (4)N2—S2—C20—C21123.4 (4)
O1—C1—C2—C3−72.3 (5)O7—S2—C20—C25−179.7 (3)
N1—C2—C3—C4−65.2 (5)O8—S2—C20—C2551.7 (4)
C1—C2—C3—C4170.6 (4)N2—S2—C20—C25−59.9 (4)
C2—C3—C4—C5−66.8 (6)C25—C20—C21—C22−1.9 (7)
C2—C3—C4—C6168.2 (5)S2—C20—C21—C22174.9 (3)
O4—S1—C7—C8−1.2 (4)C20—C21—C22—C230.3 (7)
O3—S1—C7—C8129.5 (4)C21—C22—C23—C241.1 (7)
N1—S1—C7—C8−117.9 (4)C21—C22—C23—C26−178.4 (5)
O4—S1—C7—C12177.0 (3)C22—C23—C24—C25−0.9 (8)
O3—S1—C7—C12−52.3 (4)C26—C23—C24—C25178.6 (5)
N1—S1—C7—C1260.3 (4)C23—C24—C25—C20−0.7 (8)
C12—C7—C8—C9−1.2 (7)C21—C20—C25—C242.1 (7)
S1—C7—C8—C9177.0 (4)S2—C20—C25—C24−174.7 (4)
Symmetry codes: (i) x−1, y, z; (ii) x+1, y, z.
Acknowledgements top

The authors thank the National Natural Science Foundation of China (No. 20671073), NingXia Natural Gas Transferring Key Laboratory (No. 2004007), the Science and Technology Foundation of Weifang, and Weifang University for research grants.

references
References top

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Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of Göttingen, Germany.

Tai, X.-S., Liu, W.-Y., Liu, Y.-Z. & Li, Y.-Z. (2005). Acta Cryst. E61, o389–o390.