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A single-crystal X-ray diffraction study of the effect of cooling down to 100 K on the β-form of chlorpropamide, 4-chloro-N-(propylaminocarbonyl)benzenesulfonamide, has revealed reversible phase transitions at ∼ 257 K and between 150 and 125 K: β (Pbcn, Z′ = 1) [if and only if] βII (P2/c, Z′ = 2) [if and only if] βIII (P2/n, a′ = 2a, Z′ = 4); the sequence corresponds to cooling. Despite changes in the space group and number of symmetry-independent molecules, the volume per molecule changes continuously in the temperature range 100–300 K. The phase transition at ∼ 257 K is accompanied by non-merohedral twinning, which is preserved on further cooling and through the second phase transition, but the original single crystal does not crack. DSC (differential scanning calorimetry) and X-ray powder diffraction investigations confirm the phase transitions. Twinning disappears on heating as the reverse transformations take place. The second phase transition is related to a change in conformation of the alkyl tail from trans to gauche in 1/4 of the molecules, regularly distributed in the space. Possible reasons for the increase in Z′ upon cooling are discussed in comparison to other reported examples of processes (crystallization, phase transitions) in which organic crystals with Z′ > 1 have been formed. Implications for pharmaceutical applications are discussed.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768111004290/gp5041sup1.cif
Contains datablocks bIICPA200K, bIIICPA100K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768111004290/gp5041bIICPA200Ksup2.hkl
Contains datablock bIICPA200K

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108768111004290/gp5041bIIICPA100Ksup3.hkl
Contains datablock bIIICPA100K

txt

Text file https://doi.org/10.1107/S0108768111004290/gp5041sup4.txt
CIF of chlorpropamide before cooling cycle

CCDC references: 822666; 822667

Computing details top

For both compounds, data collection: CrysAlis CCD (Oxford Diffraction,2008a); cell refinement: CrysAlis RED (Oxford Diffraction,2008b); data reduction: CrysAlis RED (Oxford Diffraction,2008b); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1]
[Figure 2]
[Figure 3]
[Figure 4]
[Figure 5]
[Figure 6]
[Figure 7]
[Figure 8]
[Figure 9]
[Figure 10]
(bIICPA200K) 4-chloro-N-((propylaminocarbonyl)benzenesulfonamide top
Crystal data top
C10H13ClN2O3SF(000) = 1152
Mr = 276.73Dx = 1.423 Mg m3
Monoclinic, P2/cMelting point: phase transition K
Hall symbol: -P 2ycMo Kα radiation, λ = 0.71073 Å
a = 14.5882 (5) ÅCell parameters from 13850 reflections
b = 9.2584 (2) Åθ = 2.8–29.2°
c = 19.1532 (6) ŵ = 0.46 mm1
β = 93.260 (3)°T = 200 K
V = 2582.71 (13) Å3Block, colourless
Z = 80.32 × 0.20 × 0.08 mm
Data collection top
Oxford Diffraction KM4 CCD
diffractometer
7720 independent reflections
Radiation source: Enhance (Mo) X-ray Source2794 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.111
Detector resolution: 10.3457 pixels mm-1θmax = 25.4°, θmin = 2.8°
ω scansh = 1717
Absorption correction: multi-scan
CrysAlis RED (Oxford Diffraction, 2008)
k = 1111
Tmin = 0.899, Tmax = 0.965l = 2323
53248 measured reflections
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)] = 0.055Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.147H-atom parameters constrained
S = 0.75 w = 1/[σ2(Fo2) + (0.0498P)2]
where P = (Fo2 + 2Fc2)/3
7720 reflections(Δ/σ)max < 0.001
310 parametersΔρmax = 0.40 e Å3
0 restraintsΔρmin = 0.30 e Å3
Crystal data top
C10H13ClN2O3SV = 2582.71 (13) Å3
Mr = 276.73Z = 8
Monoclinic, P2/cMo Kα radiation
a = 14.5882 (5) ŵ = 0.46 mm1
b = 9.2584 (2) ÅT = 200 K
c = 19.1532 (6) Å0.32 × 0.20 × 0.08 mm
β = 93.260 (3)°
Data collection top
Oxford Diffraction KM4 CCD
diffractometer
7720 independent reflections
Absorption correction: multi-scan
CrysAlis RED (Oxford Diffraction, 2008)
2794 reflections with I > 2σ(I)
Tmin = 0.899, Tmax = 0.965Rint = 0.111
53248 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0550 restraints
wR(F2) = 0.147H-atom parameters constrained
S = 0.75Δρmax = 0.40 e Å3
7720 reflectionsΔρmin = 0.30 e Å3
310 parameters
Special details top

Experimental. The data were processed using CrysAlis RED (Oxford Diffraction, 2008). This program has determined the orientation matrices of the twin components, determined the overlapping degree, merged equivalents. There were 8202 isolated (Rint = 0.051) and 53248 overlapped reflections (Rint = 0.111) of component 1. Twin component ratio 0.73:0.27.

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
Cl110.16683 (11)0.51394 (16)0.08137 (7)0.0822 (5)
S110.10693 (8)0.68692 (13)0.39003 (6)0.0501 (3)
O110.0449 (2)0.8069 (3)0.39041 (17)0.0619 (9)
O120.0868 (2)0.5584 (3)0.42699 (16)0.0599 (9)
O130.2854 (2)0.5437 (3)0.41974 (18)0.0617 (10)
N110.2031 (2)0.7548 (4)0.42096 (19)0.0426 (10)
H11N0.20390.84470.43590.051*
N120.3607 (3)0.7540 (4)0.4347 (2)0.0485 (10)
H12N0.35510.84850.43630.058*
C110.1514 (3)0.5624 (6)0.1668 (2)0.0613 (14)
C120.1423 (3)0.7065 (6)0.1842 (3)0.0676 (15)
H120.14580.77910.14940.081*
C130.1281 (3)0.7440 (5)0.2523 (3)0.0566 (14)
H130.12020.84270.26410.068*
C140.1253 (3)0.6391 (4)0.3036 (2)0.0444 (12)
C150.1353 (3)0.4973 (5)0.2844 (2)0.0541 (13)
H150.13360.42430.31920.065*
C160.1476 (3)0.4575 (5)0.2163 (3)0.0620 (14)
H160.15350.35860.20410.074*
C170.2859 (3)0.6754 (5)0.4248 (2)0.0471 (12)
C180.4529 (3)0.6912 (6)0.4433 (3)0.0619 (14)
H18A0.44880.59460.46500.074*
H18B0.49150.75280.47540.074*
C190.4978 (3)0.6773 (6)0.3752 (3)0.0706 (16)
H19A0.50310.77400.35380.085*
H19B0.45900.61670.34280.085*
C200.5937 (4)0.6094 (6)0.3851 (4)0.111 (3)
H20A0.63340.67210.41490.167*
H20B0.62000.59800.33950.167*
H20C0.58890.51450.40740.167*
Cl210.29708 (11)0.00088 (16)0.07013 (7)0.0840 (5)
S210.40918 (8)0.18721 (13)0.37561 (7)0.0515 (3)
O210.4698 (2)0.3092 (3)0.37311 (18)0.0654 (10)
O220.4384 (2)0.0617 (3)0.41412 (16)0.0596 (9)
O230.2360 (2)0.0437 (3)0.40534 (16)0.0513 (8)
N210.3183 (3)0.2551 (4)0.40755 (19)0.0490 (11)
H21N0.31910.34680.41960.059*
N220.1671 (3)0.2502 (4)0.43610 (19)0.0462 (10)
H22N0.17320.34400.44200.055*
C210.3274 (3)0.0540 (6)0.1543 (2)0.0541 (13)
C220.3401 (4)0.1972 (6)0.1706 (3)0.0737 (16)
H220.33250.26830.13500.088*
C230.3636 (3)0.2381 (5)0.2377 (3)0.0620 (15)
H230.37150.33760.24870.074*
C240.3761 (3)0.1348 (5)0.2900 (2)0.0507 (12)
C250.3645 (3)0.0089 (5)0.2732 (2)0.0564 (13)
H250.37380.08060.30840.068*
C260.3397 (3)0.0489 (5)0.2062 (3)0.0634 (14)
H260.33080.14810.19520.076*
C270.2387 (3)0.1749 (5)0.4169 (2)0.0434 (11)
C280.0792 (3)0.1840 (5)0.4479 (3)0.0602 (14)
H28A0.04910.23760.48500.072*
H28B0.08900.08330.46400.072*
C290.0167 (3)0.1846 (6)0.3806 (4)0.102 (3)
H29A0.00790.28520.36400.122*
H29B0.04650.12960.34370.122*
C300.0709 (4)0.1216 (6)0.3924 (4)0.135 (3)
H30A0.06210.02300.41020.202*
H30B0.10850.11910.34830.202*
H30C0.10200.17950.42670.202*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl110.1129 (12)0.0893 (11)0.0438 (8)0.0141 (9)0.0021 (8)0.0033 (7)
S110.0575 (8)0.0371 (6)0.0563 (8)0.0031 (7)0.0076 (6)0.0060 (7)
O110.058 (2)0.0480 (18)0.080 (3)0.0100 (19)0.0075 (18)0.0110 (19)
O120.087 (3)0.0418 (19)0.052 (2)0.0216 (18)0.0179 (18)0.0004 (16)
O130.070 (2)0.0264 (18)0.087 (3)0.0053 (17)0.0103 (19)0.0054 (17)
N110.046 (2)0.0283 (18)0.055 (3)0.0020 (18)0.010 (2)0.0101 (18)
N120.051 (3)0.033 (2)0.061 (3)0.001 (2)0.002 (2)0.0052 (19)
C110.080 (4)0.058 (3)0.044 (3)0.015 (3)0.014 (3)0.004 (3)
C120.090 (4)0.058 (4)0.055 (4)0.003 (3)0.009 (3)0.027 (3)
C130.072 (4)0.036 (3)0.062 (4)0.010 (2)0.009 (3)0.008 (3)
C140.045 (3)0.032 (3)0.055 (3)0.003 (2)0.003 (2)0.004 (2)
C150.089 (4)0.034 (3)0.039 (3)0.014 (2)0.002 (3)0.006 (2)
C160.092 (4)0.041 (3)0.051 (3)0.010 (3)0.008 (3)0.002 (3)
C170.061 (3)0.032 (3)0.048 (3)0.002 (3)0.004 (2)0.002 (2)
C180.066 (4)0.060 (3)0.057 (4)0.014 (3)0.018 (3)0.007 (3)
C190.056 (3)0.050 (3)0.107 (5)0.014 (3)0.015 (3)0.017 (3)
C200.078 (4)0.061 (4)0.197 (8)0.014 (4)0.027 (5)0.023 (5)
Cl210.1168 (13)0.0887 (11)0.0458 (8)0.0056 (9)0.0026 (8)0.0015 (8)
S210.0551 (8)0.0379 (6)0.0613 (9)0.0028 (7)0.0007 (7)0.0058 (7)
O210.065 (2)0.0487 (19)0.083 (3)0.0164 (19)0.0044 (18)0.0142 (19)
O220.074 (2)0.0419 (19)0.060 (2)0.0137 (17)0.0188 (18)0.0102 (16)
O230.062 (2)0.0283 (17)0.065 (2)0.0020 (16)0.0150 (17)0.0022 (16)
N210.060 (3)0.0314 (19)0.055 (3)0.003 (2)0.001 (2)0.0119 (19)
N220.057 (3)0.036 (2)0.046 (3)0.005 (2)0.007 (2)0.0003 (19)
C210.059 (3)0.063 (3)0.040 (3)0.007 (3)0.009 (2)0.003 (3)
C220.116 (5)0.050 (3)0.055 (4)0.006 (3)0.008 (3)0.008 (3)
C230.080 (4)0.033 (3)0.075 (4)0.011 (3)0.015 (3)0.002 (3)
C240.052 (3)0.041 (3)0.059 (3)0.003 (2)0.003 (2)0.005 (2)
C250.082 (4)0.034 (3)0.054 (3)0.009 (3)0.005 (3)0.003 (2)
C260.087 (4)0.046 (3)0.058 (4)0.002 (3)0.016 (3)0.004 (3)
C270.060 (3)0.032 (3)0.039 (3)0.006 (3)0.008 (2)0.006 (2)
C280.070 (4)0.043 (3)0.070 (4)0.010 (3)0.021 (3)0.004 (3)
C290.044 (3)0.063 (4)0.195 (8)0.017 (3)0.028 (4)0.078 (4)
C300.130 (6)0.069 (5)0.201 (9)0.024 (5)0.011 (6)0.032 (5)
Geometric parameters (Å, º) top
Cl11—C111.723 (5)Cl21—C211.719 (5)
S11—O121.424 (3)S21—O221.428 (3)
S11—O111.433 (3)S21—O211.437 (3)
S11—N111.619 (4)S21—N211.618 (4)
S11—C141.748 (5)S21—C241.752 (5)
O13—C171.223 (5)O23—C271.235 (5)
N11—C171.412 (5)N21—C271.399 (5)
N11—H11N0.8800N21—H21N0.8800
N12—C171.316 (5)N22—C271.324 (5)
N12—C181.466 (5)N22—C281.450 (5)
N12—H12N0.8800N22—H22N0.8800
C11—C161.361 (6)C21—C221.372 (7)
C11—C121.384 (7)C21—C261.381 (6)
C12—C131.375 (7)C22—C231.365 (6)
C12—H120.9500C22—H220.9500
C13—C141.385 (6)C23—C241.389 (6)
C13—H130.9500C23—H230.9500
C14—C151.374 (6)C24—C251.377 (6)
C15—C161.377 (6)C25—C261.364 (6)
C15—H150.9500C25—H250.9500
C16—H160.9500C26—H260.9500
C18—C191.498 (7)C28—C291.536 (7)
C18—H18A0.9900C28—H28A0.9900
C18—H18B0.9900C28—H28B0.9900
C19—C201.535 (6)C29—C301.436 (7)
C19—H19A0.9900C29—H29A0.9900
C19—H19B0.9900C29—H29B0.9900
C20—H20A0.9800C30—H30A0.9800
C20—H20B0.9800C30—H30B0.9800
C20—H20C0.9800C30—H30C0.9800
O12—S11—O11119.8 (2)O22—S21—O21119.38 (19)
O12—S11—N11110.0 (2)O22—S21—N21110.3 (2)
O11—S11—N11103.38 (19)O21—S21—N21103.1 (2)
O12—S11—C14107.83 (19)O22—S21—C24108.5 (2)
O11—S11—C14109.4 (2)O21—S21—C24108.9 (2)
N11—S11—C14105.6 (2)N21—S21—C24105.9 (2)
C17—N11—S11122.5 (3)C27—N21—S21123.1 (3)
C17—N11—H11N118.7C27—N21—H21N118.4
S11—N11—H11N118.7S21—N21—H21N118.4
C17—N12—C18123.0 (4)C27—N22—C28122.6 (4)
C17—N12—H12N118.5C27—N22—H22N118.7
C18—N12—H12N118.5C28—N22—H22N118.7
C16—C11—C12120.8 (5)C22—C21—C26119.5 (5)
C16—C11—Cl11119.2 (4)C22—C21—Cl21120.9 (4)
C12—C11—Cl11120.0 (4)C26—C21—Cl21119.6 (4)
C13—C12—C11119.6 (4)C23—C22—C21120.4 (5)
C13—C12—H12120.2C23—C22—H22119.8
C11—C12—H12120.2C21—C22—H22119.8
C12—C13—C14120.5 (4)C22—C23—C24120.2 (4)
C12—C13—H13119.7C22—C23—H23119.9
C14—C13—H13119.7C24—C23—H23119.9
C15—C14—C13118.1 (4)C25—C24—C23119.2 (5)
C15—C14—S11121.3 (3)C25—C24—S21120.6 (4)
C13—C14—S11120.5 (3)C23—C24—S21120.1 (4)
C14—C15—C16122.1 (4)C26—C25—C24120.2 (5)
C14—C15—H15119.0C26—C25—H25119.9
C16—C15—H15119.0C24—C25—H25119.9
C11—C16—C15118.8 (5)C25—C26—C21120.5 (5)
C11—C16—H16120.6C25—C26—H26119.8
C15—C16—H16120.6C21—C26—H26119.8
O13—C17—N12124.3 (5)O23—C27—N22123.4 (4)
O13—C17—N11120.9 (4)O23—C27—N21121.1 (4)
N12—C17—N11114.8 (4)N22—C27—N21115.5 (4)
N12—C18—C19112.4 (4)N22—C28—C29110.9 (4)
N12—C18—H18A109.1N22—C28—H28A109.5
C19—C18—H18A109.1C29—C28—H28A109.5
N12—C18—H18B109.1N22—C28—H28B109.5
C19—C18—H18B109.1C29—C28—H28B109.5
H18A—C18—H18B107.9H28A—C28—H28B108.1
C18—C19—C20111.6 (5)C30—C29—C28111.0 (5)
C18—C19—H19A109.3C30—C29—H29A109.4
C20—C19—H19A109.3C28—C29—H29A109.4
C18—C19—H19B109.3C30—C29—H29B109.4
C20—C19—H19B109.3C28—C29—H29B109.4
H19A—C19—H19B108.0H29A—C29—H29B108.0
C19—C20—H20A109.5C29—C30—H30A109.5
C19—C20—H20B109.5C29—C30—H30B109.5
H20A—C20—H20B109.5H30A—C30—H30B109.5
C19—C20—H20C109.5C29—C30—H30C109.5
H20A—C20—H20C109.5H30A—C30—H30C109.5
H20B—C20—H20C109.5H30B—C30—H30C109.5
O12—S11—N11—C1755.8 (4)O22—S21—N21—C2754.0 (4)
O11—S11—N11—C17175.1 (4)O21—S21—N21—C27177.5 (4)
C14—S11—N11—C1760.3 (4)C24—S21—N21—C2763.2 (4)
C16—C11—C12—C130.9 (8)C26—C21—C22—C230.7 (8)
Cl11—C11—C12—C13178.7 (4)Cl21—C21—C22—C23179.6 (4)
C11—C12—C13—C141.7 (8)C21—C22—C23—C240.8 (8)
C12—C13—C14—C151.2 (7)C22—C23—C24—C250.1 (8)
C12—C13—C14—S11179.8 (4)C22—C23—C24—S21178.3 (4)
O12—S11—C14—C1511.5 (4)O22—S21—C24—C2512.1 (5)
O11—S11—C14—C15143.3 (4)O21—S21—C24—C25143.5 (4)
N11—S11—C14—C15106.0 (4)N21—S21—C24—C25106.3 (4)
O12—S11—C14—C13167.0 (4)O22—S21—C24—C23166.1 (4)
O11—S11—C14—C1335.2 (4)O21—S21—C24—C2334.7 (5)
N11—S11—C14—C1375.4 (4)N21—S21—C24—C2375.5 (4)
C13—C14—C15—C160.1 (7)C23—C24—C25—C261.0 (8)
S11—C14—C15—C16178.5 (4)S21—C24—C25—C26179.3 (4)
C12—C11—C16—C150.4 (8)C24—C25—C26—C211.1 (8)
Cl11—C11—C16—C15180.0 (4)C22—C21—C26—C250.2 (8)
C14—C15—C16—C110.9 (8)Cl21—C21—C26—C25179.5 (4)
C18—N12—C17—O132.2 (8)C28—N22—C27—O232.3 (7)
C18—N12—C17—N11177.2 (4)C28—N22—C27—N21179.8 (4)
S11—N11—C17—O1316.5 (7)S21—N21—C27—O235.0 (6)
S11—N11—C17—N12164.1 (3)S21—N21—C27—N22172.6 (3)
C17—N12—C18—C1991.5 (6)C27—N22—C28—C2991.2 (6)
N12—C18—C19—C20179.2 (4)N22—C28—C29—C30179.0 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11N···O23i0.882.002.737 (4)141
N12—H12N···O22i0.882.373.100 (5)141
N12—H12N···O23i0.882.553.271 (5)140
N21—H21N···O130.881.892.728 (4)159
N22—H22N···O120.882.363.086 (5)140
N22—H22N···O130.882.523.244 (5)140
Symmetry code: (i) x, y+1, z.
(bIIICPA100K) 4-chloro-N-((propylaminocarbonyl)benzenesulfonamide top
Crystal data top
C10H13ClN2O3SF(000) = 2304
Mr = 276.73Dx = 1.463 Mg m3
Monoclinic, P2/nMelting point: phase transition K
Hall symbol: -P 2yacMo Kα radiation, λ = 0.71073 Å
a = 28.4475 (12) ÅCell parameters from 9693 reflections
b = 9.2322 (3) Åθ = 3.1–29.3°
c = 19.2298 (7) ŵ = 0.47 mm1
β = 95.562 (4)°T = 100 K
V = 5026.6 (3) Å3Block, colourless
Z = 160.22 × 0.15 × 0.06 mm
Data collection top
Oxford Diffraction KM4 CCD
diffractometer
14436 independent reflections
Radiation source: Enhance (Mo) X-ray Source6814 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.087
Detector resolution: 10.3457 pixels mm-1θmax = 25.7°, θmin = 3.1°
ω scansh = 3334
Absorption correction: multi-scan
CrysAlis RED (Oxford Diffraction, 2008)
k = 1111
Tmin = 0.946, Tmax = 0.973l = 2323
42040 measured reflections
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139H-atom parameters constrained
S = 0.81 w = 1/[σ2(Fo2) + (0.0519P)2]
where P = (Fo2 + 2Fc2)/3
14436 reflections(Δ/σ)max < 0.001
618 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.45 e Å3
Crystal data top
C10H13ClN2O3SV = 5026.6 (3) Å3
Mr = 276.73Z = 16
Monoclinic, P2/nMo Kα radiation
a = 28.4475 (12) ŵ = 0.47 mm1
b = 9.2322 (3) ÅT = 100 K
c = 19.2298 (7) Å0.22 × 0.15 × 0.06 mm
β = 95.562 (4)°
Data collection top
Oxford Diffraction KM4 CCD
diffractometer
14436 independent reflections
Absorption correction: multi-scan
CrysAlis RED (Oxford Diffraction, 2008)
6814 reflections with I > 2σ(I)
Tmin = 0.946, Tmax = 0.973Rint = 0.087
42040 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.139H-atom parameters constrained
S = 0.81Δρmax = 0.37 e Å3
14436 reflectionsΔρmin = 0.45 e Å3
618 parameters
Special details top

Experimental. The data were processed using CrysAlis RED (Oxford Diffraction, 2008). This program has determined the orientation matrices of the twin components, determined the overlapping degree, merged equivalents. There were 9590 isolated (Rint = 0.065) and 42040 overlapped reflections (Rint = 0.087) of component 1. Twin component ratio 0.56:0.44.

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
S110.21089 (5)0.71308 (13)0.37489 (8)0.0205 (3)
Cl110.13654 (5)0.52901 (15)0.07238 (8)0.0360 (4)
O110.24094 (12)0.8357 (3)0.3716 (2)0.0278 (9)
O120.22796 (12)0.5854 (3)0.4118 (2)0.0233 (9)
O130.12415 (11)0.5664 (3)0.40638 (19)0.0197 (9)
N110.16538 (14)0.7787 (4)0.4097 (2)0.0191 (10)
H11N0.16620.86980.42310.023*
N120.08929 (15)0.7716 (4)0.4398 (2)0.0203 (10)
H12N0.09280.86530.44680.024*
C110.15720 (19)0.5804 (5)0.1573 (3)0.0222 (13)
C120.1624 (2)0.7259 (5)0.1722 (3)0.0321 (15)
H120.15470.79700.13720.039*
C130.17886 (19)0.7655 (6)0.2390 (3)0.0259 (14)
H130.18300.86520.25020.031*
C140.18954 (18)0.6611 (5)0.2905 (3)0.0219 (13)
C150.18325 (18)0.5164 (5)0.2737 (3)0.0207 (13)
H150.19000.44440.30860.025*
C160.1671 (2)0.4761 (5)0.2060 (3)0.0255 (13)
H160.16310.37670.19400.031*
C170.12480 (18)0.6968 (5)0.4193 (3)0.0165 (12)
C180.04397 (19)0.7037 (5)0.4516 (3)0.0263 (14)
H18A0.02820.76260.48550.032*
H18B0.05000.60640.47220.032*
C190.01092 (19)0.6890 (5)0.3837 (3)0.0292 (15)
H19A0.00460.78610.36320.035*
H19B0.02660.63020.34970.035*
C200.03458 (18)0.6193 (6)0.3969 (3)0.0314 (14)
H20A0.02880.51850.41130.047*
H20B0.05630.62180.35410.047*
H20C0.04860.67170.43410.047*
S210.05747 (5)0.20420 (13)0.39707 (7)0.0193 (3)
Cl210.07533 (5)0.03885 (14)0.08621 (7)0.0272 (3)
O210.02457 (12)0.3210 (3)0.39749 (19)0.0235 (9)
O220.04981 (13)0.0740 (3)0.43476 (18)0.0232 (9)
O230.15094 (13)0.0702 (3)0.4252 (2)0.0275 (10)
N210.10740 (14)0.2770 (4)0.4269 (2)0.0187 (10)
H21N0.10750.36690.44220.022*
N220.18848 (15)0.2866 (4)0.4349 (2)0.0219 (11)
H22N0.18490.38130.43440.026*
C210.07206 (17)0.0859 (6)0.1726 (3)0.0213 (13)
C220.07025 (19)0.2306 (5)0.1914 (3)0.0275 (14)
H220.07140.30420.15710.033*
C230.06678 (19)0.2662 (5)0.2593 (3)0.0257 (14)
H230.06590.36520.27260.031*
C240.06450 (18)0.1570 (5)0.3101 (3)0.0190 (12)
C250.06601 (19)0.0134 (5)0.2904 (3)0.0251 (14)
H250.06410.06090.32420.030*
C260.07030 (19)0.0222 (5)0.2218 (3)0.0239 (13)
H260.07200.12090.20840.029*
C270.14990 (19)0.2019 (5)0.4291 (3)0.0182 (12)
C280.23616 (19)0.2271 (5)0.4420 (3)0.0275 (14)
H28A0.23640.13670.46980.033*
H28B0.25770.29690.46800.033*
C290.2547 (2)0.1944 (5)0.3719 (3)0.0289 (14)
H29A0.25510.28490.34440.035*
H29B0.23300.12550.34550.035*
C300.30442 (19)0.1297 (5)0.3811 (3)0.0338 (16)
H30A0.32640.20060.40400.051*
H30B0.31440.10480.33520.051*
H30C0.30430.04210.40990.051*
S310.55663 (5)0.15921 (12)0.40022 (7)0.0174 (3)
Cl310.57454 (5)0.00535 (14)0.08763 (7)0.0278 (3)
O310.52418 (12)0.2755 (3)0.40220 (19)0.0228 (9)
O320.54986 (12)0.0270 (3)0.43614 (18)0.0195 (8)
O330.64992 (13)0.0231 (3)0.4279 (2)0.0294 (10)
N310.60691 (14)0.2305 (4)0.4314 (2)0.0161 (10)
H31N0.60700.31930.44790.019*
N320.68793 (15)0.2388 (4)0.4386 (2)0.0228 (11)
H32N0.68420.33340.43940.027*
C310.57098 (18)0.0495 (5)0.1742 (3)0.0200 (12)
C320.56652 (19)0.1927 (5)0.1936 (3)0.0261 (14)
H320.56630.26730.15950.031*
C330.5624 (2)0.2267 (5)0.2626 (3)0.0248 (13)
H330.55930.32500.27610.030*
C340.56294 (17)0.1169 (5)0.3128 (3)0.0167 (12)
C350.56814 (18)0.0276 (5)0.2926 (3)0.0220 (13)
H350.56910.10290.32640.026*
C360.57180 (19)0.0596 (5)0.2233 (3)0.0230 (13)
H360.57490.15750.20930.028*
C370.6501 (2)0.1558 (5)0.4328 (3)0.0195 (13)
C380.73638 (19)0.1797 (6)0.4439 (3)0.0267 (14)
H38A0.73740.08950.47180.032*
H38B0.75820.25020.46870.032*
C390.75302 (19)0.1477 (5)0.3733 (3)0.0279 (14)
H39A0.75340.23850.34600.034*
H39B0.73070.08000.34750.034*
C400.80181 (19)0.0818 (6)0.3804 (3)0.0339 (15)
H40A0.82380.14760.40690.051*
H40B0.81220.06600.33380.051*
H40C0.80110.01100.40500.051*
S410.70684 (5)0.66682 (13)0.37669 (8)0.0204 (3)
Cl410.64736 (5)0.47530 (14)0.07030 (7)0.0308 (3)
O410.73630 (12)0.7908 (3)0.3747 (2)0.0250 (9)
O420.72302 (12)0.5403 (3)0.41542 (18)0.0227 (9)
O430.62015 (12)0.5163 (3)0.40394 (19)0.0200 (8)
N410.65923 (15)0.7324 (4)0.4084 (2)0.0209 (11)
H41N0.65870.82490.41940.025*
N420.58415 (14)0.7202 (4)0.4404 (2)0.0171 (10)
H42N0.58680.81470.44570.021*
C410.66228 (18)0.5311 (5)0.1555 (3)0.0239 (13)
C420.66840 (19)0.6751 (5)0.1707 (3)0.0246 (14)
H420.66360.74580.13480.030*
C430.68154 (18)0.7163 (6)0.2385 (3)0.0257 (14)
H430.68570.81600.24970.031*
C440.68874 (18)0.6126 (5)0.2907 (3)0.0197 (13)
C450.68143 (19)0.4673 (5)0.2756 (3)0.0241 (13)
H450.68530.39670.31160.029*
C460.66819 (19)0.4259 (6)0.2062 (3)0.0251 (13)
H460.66340.32670.19450.030*
C470.62023 (19)0.6481 (5)0.4184 (3)0.0182 (13)
C480.53991 (18)0.6507 (5)0.4565 (3)0.0270 (14)
H48A0.53190.68470.50270.032*
H48B0.54480.54460.45950.032*
C490.49769 (19)0.6831 (6)0.4011 (3)0.0270 (14)
H49A0.46830.64470.41790.032*
H49B0.49410.78930.39580.032*
C500.5041 (2)0.6170 (6)0.3305 (3)0.0420 (17)
H50A0.53570.64020.31750.063*
H50B0.48030.65650.29530.063*
H50C0.50050.51160.33300.063*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S110.0188 (8)0.0172 (7)0.0255 (9)0.0025 (6)0.0024 (7)0.0019 (6)
Cl110.0467 (10)0.0399 (8)0.0204 (9)0.0005 (7)0.0019 (7)0.0022 (6)
O110.019 (2)0.023 (2)0.041 (3)0.0066 (16)0.0037 (19)0.0063 (17)
O120.020 (2)0.0202 (19)0.028 (2)0.0028 (15)0.0061 (18)0.0012 (16)
O130.017 (2)0.0110 (18)0.032 (2)0.0047 (14)0.0064 (17)0.0025 (15)
N110.019 (3)0.009 (2)0.030 (3)0.0004 (18)0.007 (2)0.0010 (18)
N120.023 (3)0.011 (2)0.027 (3)0.0008 (19)0.005 (2)0.0015 (18)
C110.022 (3)0.029 (3)0.015 (3)0.000 (2)0.001 (2)0.001 (2)
C120.049 (4)0.021 (3)0.026 (4)0.008 (3)0.002 (3)0.010 (3)
C130.038 (4)0.018 (3)0.022 (4)0.006 (2)0.002 (3)0.002 (2)
C140.015 (3)0.024 (3)0.026 (4)0.005 (2)0.000 (2)0.005 (2)
C150.026 (3)0.014 (3)0.022 (4)0.003 (2)0.004 (2)0.001 (2)
C160.038 (4)0.010 (3)0.027 (4)0.004 (2)0.003 (3)0.000 (2)
C170.011 (3)0.020 (3)0.019 (3)0.000 (2)0.002 (2)0.006 (2)
C180.033 (4)0.017 (3)0.031 (4)0.003 (2)0.015 (3)0.001 (2)
C190.037 (4)0.014 (3)0.035 (4)0.002 (2)0.004 (3)0.008 (2)
C200.028 (3)0.027 (3)0.040 (4)0.004 (3)0.007 (3)0.016 (3)
S210.0207 (8)0.0165 (7)0.0211 (8)0.0005 (6)0.0048 (6)0.0010 (5)
Cl210.0282 (8)0.0346 (7)0.0190 (9)0.0037 (6)0.0026 (6)0.0005 (6)
O210.022 (2)0.0231 (19)0.025 (2)0.0023 (16)0.0016 (18)0.0015 (16)
O220.034 (2)0.0201 (19)0.016 (2)0.0035 (16)0.0063 (18)0.0020 (15)
O230.031 (2)0.0114 (19)0.041 (3)0.0053 (16)0.005 (2)0.0032 (16)
N210.019 (2)0.014 (2)0.024 (3)0.0010 (18)0.008 (2)0.0095 (18)
N220.025 (3)0.011 (2)0.028 (3)0.0015 (19)0.004 (2)0.0011 (18)
C210.010 (3)0.035 (3)0.017 (3)0.008 (2)0.004 (2)0.000 (2)
C220.035 (4)0.023 (3)0.023 (4)0.004 (2)0.007 (3)0.010 (2)
C230.036 (4)0.012 (3)0.028 (4)0.001 (2)0.002 (3)0.003 (2)
C240.023 (3)0.016 (3)0.019 (3)0.000 (2)0.006 (2)0.000 (2)
C250.032 (3)0.019 (3)0.024 (4)0.004 (2)0.003 (3)0.005 (2)
C260.032 (3)0.018 (3)0.021 (4)0.003 (2)0.003 (3)0.001 (2)
C270.026 (3)0.017 (3)0.013 (3)0.004 (2)0.004 (3)0.004 (2)
C280.030 (4)0.020 (3)0.031 (4)0.002 (2)0.009 (3)0.000 (2)
C290.036 (4)0.018 (3)0.033 (4)0.002 (2)0.002 (3)0.000 (2)
C300.027 (4)0.020 (3)0.055 (5)0.007 (2)0.006 (3)0.005 (3)
S310.0208 (8)0.0145 (7)0.0174 (8)0.0003 (6)0.0045 (6)0.0009 (5)
Cl310.0303 (8)0.0346 (8)0.0185 (9)0.0047 (6)0.0015 (6)0.0011 (6)
O310.022 (2)0.0186 (18)0.029 (2)0.0009 (15)0.0092 (18)0.0006 (16)
O320.031 (2)0.0142 (17)0.013 (2)0.0047 (15)0.0032 (17)0.0019 (14)
O330.029 (2)0.0139 (19)0.045 (3)0.0059 (16)0.004 (2)0.0055 (16)
N310.019 (2)0.008 (2)0.023 (3)0.0001 (17)0.007 (2)0.0055 (17)
N320.024 (3)0.013 (2)0.031 (3)0.003 (2)0.001 (2)0.0028 (19)
C310.018 (3)0.023 (3)0.018 (3)0.003 (2)0.000 (2)0.003 (2)
C320.030 (4)0.024 (3)0.025 (4)0.001 (2)0.006 (3)0.006 (2)
C330.033 (3)0.018 (3)0.024 (4)0.002 (2)0.003 (3)0.005 (2)
C340.010 (3)0.018 (3)0.023 (3)0.000 (2)0.005 (2)0.001 (2)
C350.027 (3)0.018 (3)0.021 (4)0.001 (2)0.004 (3)0.009 (2)
C360.031 (3)0.019 (3)0.018 (3)0.001 (2)0.001 (3)0.007 (2)
C370.036 (4)0.008 (3)0.014 (3)0.006 (2)0.004 (3)0.004 (2)
C380.023 (3)0.026 (3)0.029 (4)0.000 (2)0.006 (3)0.001 (2)
C390.029 (3)0.018 (3)0.035 (4)0.002 (2)0.006 (3)0.004 (2)
C400.031 (4)0.021 (3)0.050 (4)0.003 (3)0.002 (3)0.001 (3)
S410.0211 (8)0.0150 (7)0.0255 (9)0.0013 (6)0.0035 (7)0.0021 (6)
Cl410.0344 (8)0.0356 (8)0.0216 (8)0.0041 (6)0.0005 (7)0.0020 (6)
O410.016 (2)0.0220 (19)0.038 (3)0.0054 (15)0.0053 (18)0.0016 (17)
O420.021 (2)0.0264 (19)0.019 (2)0.0035 (16)0.0101 (17)0.0037 (15)
O430.025 (2)0.0149 (19)0.020 (2)0.0005 (15)0.0014 (17)0.0020 (15)
N410.031 (3)0.009 (2)0.025 (3)0.0031 (19)0.012 (2)0.0061 (18)
N420.017 (2)0.013 (2)0.022 (3)0.0042 (18)0.001 (2)0.0008 (18)
C410.019 (3)0.029 (3)0.023 (3)0.000 (2)0.003 (3)0.000 (2)
C420.030 (3)0.016 (3)0.029 (4)0.001 (2)0.013 (3)0.012 (2)
C430.032 (4)0.017 (3)0.029 (4)0.001 (2)0.007 (3)0.001 (2)
C440.018 (3)0.019 (3)0.023 (4)0.004 (2)0.004 (2)0.000 (2)
C450.035 (4)0.015 (3)0.024 (4)0.002 (2)0.008 (3)0.005 (2)
C460.031 (3)0.024 (3)0.019 (3)0.001 (2)0.000 (3)0.010 (2)
C470.028 (3)0.011 (3)0.016 (3)0.002 (2)0.005 (3)0.006 (2)
C480.025 (3)0.026 (3)0.032 (4)0.001 (2)0.012 (3)0.009 (2)
C490.022 (3)0.031 (3)0.025 (3)0.006 (2)0.009 (3)0.002 (3)
C500.051 (4)0.027 (3)0.045 (4)0.005 (3)0.007 (3)0.003 (3)
Geometric parameters (Å, º) top
S11—O111.424 (3)S31—O311.419 (3)
S11—O121.436 (4)S31—O321.425 (3)
S11—N111.630 (4)S31—N311.634 (4)
S11—C141.743 (6)S31—C341.753 (5)
Cl11—C111.746 (5)Cl31—C311.727 (5)
O13—C171.229 (5)O33—C371.229 (5)
N11—C171.407 (6)N31—C371.406 (6)
N11—H11N0.8800N31—H31N0.8800
N12—C171.315 (6)N32—C371.317 (6)
N12—C181.470 (6)N32—C381.477 (6)
N12—H12N0.8800N32—H32N0.8800
C11—C161.355 (7)C31—C361.379 (7)
C11—C121.379 (7)C31—C321.382 (7)
C12—C131.373 (8)C32—C331.380 (8)
C12—H120.9500C32—H320.9500
C13—C141.395 (7)C33—C341.399 (7)
C13—H130.9500C33—H330.9500
C14—C151.382 (7)C34—C351.401 (7)
C15—C161.389 (8)C35—C361.378 (7)
C15—H150.9500C35—H350.9500
C16—H160.9500C36—H360.9500
C18—C191.538 (7)C38—C391.509 (8)
C18—H18A0.9900C38—H38A0.9900
C18—H18B0.9900C38—H38B0.9900
C19—C201.489 (7)C39—C401.509 (7)
C19—H19A0.9900C39—H39A0.9900
C19—H19B0.9900C39—H39B0.9900
C20—H20A0.9800C40—H40A0.9800
C20—H20B0.9800C40—H40B0.9800
C20—H20C0.9800C40—H40C0.9800
S21—O211.428 (3)S41—O411.421 (3)
S21—O221.431 (3)S41—O421.437 (4)
S21—N211.625 (4)S41—N411.653 (4)
S21—C241.759 (5)S41—C441.756 (6)
Cl21—C211.728 (5)Cl41—C411.730 (6)
O23—C271.219 (5)O43—C471.248 (5)
N21—C271.391 (6)N41—C471.384 (6)
N21—H21N0.8800N41—H41N0.8800
N22—C271.343 (6)N42—C471.327 (6)
N22—C281.458 (6)N42—C481.472 (6)
N22—H22N0.8800N42—H42N0.8800
C21—C261.380 (7)C41—C421.370 (7)
C21—C221.386 (7)C41—C461.375 (7)
C22—C231.359 (8)C42—C431.375 (8)
C22—H220.9500C42—H420.9500
C23—C241.410 (7)C43—C441.388 (8)
C23—H230.9500C43—H430.9500
C24—C251.381 (6)C44—C451.384 (7)
C25—C261.376 (7)C45—C461.403 (7)
C25—H250.9500C45—H450.9500
C26—H260.9500C46—H460.9500
C28—C291.524 (8)C48—C491.555 (7)
C28—H28A0.9900C48—H48A0.9900
C28—H28B0.9900C48—H48B0.9900
C29—C301.531 (7)C49—C501.515 (8)
C29—H29A0.9900C49—H49A0.9900
C29—H29B0.9900C49—H49B0.9900
C30—H30A0.9800C50—H50A0.9800
C30—H30B0.9800C50—H50B0.9800
C30—H30C0.9800C50—H50C0.9800
O11—S11—O12119.9 (2)O31—S31—O32121.1 (2)
O11—S11—N11103.1 (2)O31—S31—N31103.6 (2)
O12—S11—N11110.2 (2)O32—S31—N31108.8 (2)
O11—S11—C14109.5 (2)O31—S31—C34108.8 (2)
O12—S11—C14107.7 (2)O32—S31—C34107.8 (2)
N11—S11—C14105.4 (2)N31—S31—C34105.9 (2)
C17—N11—S11123.3 (3)C37—N31—S31122.8 (3)
C17—N11—H11N118.3C37—N31—H31N118.6
S11—N11—H11N118.3S31—N31—H31N118.6
C17—N12—C18122.2 (4)C37—N32—C38122.7 (4)
C17—N12—H12N118.9C37—N32—H32N118.6
C18—N12—H12N118.9C38—N32—H32N118.6
C16—C11—C12122.5 (5)C36—C31—C32120.7 (5)
C16—C11—Cl11118.8 (4)C36—C31—Cl31119.3 (4)
C12—C11—Cl11118.7 (4)C32—C31—Cl31120.0 (4)
C13—C12—C11118.3 (5)C33—C32—C31119.7 (5)
C13—C12—H12120.8C33—C32—H32120.2
C11—C12—H12120.8C31—C32—H32120.2
C12—C13—C14120.8 (5)C32—C33—C34120.1 (5)
C12—C13—H13119.6C32—C33—H33119.9
C14—C13—H13119.6C34—C33—H33119.9
C15—C14—C13119.2 (5)C33—C34—C35119.6 (5)
C15—C14—S11120.6 (4)C33—C34—S31120.3 (4)
C13—C14—S11120.2 (4)C35—C34—S31120.1 (4)
C14—C15—C16120.1 (5)C36—C35—C34119.5 (5)
C14—C15—H15119.9C36—C35—H35120.3
C16—C15—H15119.9C34—C35—H35120.3
C11—C16—C15119.1 (5)C35—C36—C31120.5 (5)
C11—C16—H16120.5C35—C36—H36119.8
C15—C16—H16120.5C31—C36—H36119.8
O13—C17—N12125.3 (5)O33—C37—N32125.7 (5)
O13—C17—N11119.7 (5)O33—C37—N31119.3 (5)
N12—C17—N11115.0 (4)N32—C37—N31115.0 (4)
N12—C18—C19112.4 (4)N32—C38—C39112.5 (4)
N12—C18—H18A109.1N32—C38—H38A109.1
C19—C18—H18A109.1C39—C38—H38A109.1
N12—C18—H18B109.1N32—C38—H38B109.1
C19—C18—H18B109.1C39—C38—H38B109.1
H18A—C18—H18B107.9H38A—C38—H38B107.8
C20—C19—C18111.3 (5)C38—C39—C40111.3 (5)
C20—C19—H19A109.4C38—C39—H39A109.4
C18—C19—H19A109.4C40—C39—H39A109.4
C20—C19—H19B109.4C38—C39—H39B109.4
C18—C19—H19B109.4C40—C39—H39B109.4
H19A—C19—H19B108.0H39A—C39—H39B108.0
C19—C20—H20A109.5C39—C40—H40A109.5
C19—C20—H20B109.5C39—C40—H40B109.5
H20A—C20—H20B109.5H40A—C40—H40B109.5
C19—C20—H20C109.5C39—C40—H40C109.5
H20A—C20—H20C109.5H40A—C40—H40C109.5
H20B—C20—H20C109.5H40B—C40—H40C109.5
O21—S21—O22120.0 (2)O41—S41—O42120.6 (2)
O21—S21—N21103.7 (2)O41—S41—N41102.8 (2)
O22—S21—N21109.8 (2)O42—S41—N41109.9 (2)
O21—S21—C24109.1 (2)O41—S41—C44108.9 (2)
O22—S21—C24108.1 (2)O42—S41—C44107.8 (2)
N21—S21—C24105.2 (2)N41—S41—C44106.0 (2)
C27—N21—S21122.2 (3)C47—N41—S41122.8 (3)
C27—N21—H21N118.9C47—N41—H41N118.6
S21—N21—H21N118.9S41—N41—H41N118.6
C27—N22—C28122.3 (4)C47—N42—C48123.5 (4)
C27—N22—H22N118.9C47—N42—H42N118.3
C28—N22—H22N118.9C48—N42—H42N118.3
C26—C21—C22120.9 (5)C42—C41—C46121.9 (5)
C26—C21—Cl21119.1 (4)C42—C41—Cl41120.4 (4)
C22—C21—Cl21120.0 (4)C46—C41—Cl41117.6 (4)
C23—C22—C21119.5 (5)C41—C42—C43119.3 (5)
C23—C22—H22120.3C41—C42—H42120.4
C21—C22—H22120.3C43—C42—H42120.4
C22—C23—C24120.3 (5)C42—C43—C44120.2 (5)
C22—C23—H23119.8C42—C43—H43119.9
C24—C23—H23119.8C44—C43—H43119.9
C25—C24—C23119.5 (5)C45—C44—C43120.5 (5)
C25—C24—S21120.5 (4)C45—C44—S41119.9 (4)
C23—C24—S21120.0 (4)C43—C44—S41119.6 (4)
C26—C25—C24120.0 (5)C44—C45—C46119.0 (5)
C26—C25—H25120.0C44—C45—H45120.5
C24—C25—H25120.0C46—C45—H45120.5
C25—C26—C21119.8 (5)C41—C46—C45119.0 (5)
C25—C26—H26120.1C41—C46—H46120.5
C21—C26—H26120.1C45—C46—H46120.5
O23—C27—N22124.1 (5)O43—C47—N42125.2 (5)
O23—C27—N21121.4 (5)O43—C47—N41120.1 (5)
N22—C27—N21114.4 (4)N42—C47—N41114.6 (4)
N22—C28—C29112.9 (4)N42—C48—C49113.0 (4)
N22—C28—H28A109.0N42—C48—H48A109.0
C29—C28—H28A109.0C49—C48—H48A109.0
N22—C28—H28B109.0N42—C48—H48B109.0
C29—C28—H28B109.0C49—C48—H48B109.0
H28A—C28—H28B107.8H48A—C48—H48B107.8
C28—C29—C30111.7 (5)C50—C49—C48112.6 (4)
C28—C29—H29A109.3C50—C49—H49A109.1
C30—C29—H29A109.3C48—C49—H49A109.1
C28—C29—H29B109.3C50—C49—H49B109.1
C30—C29—H29B109.3C48—C49—H49B109.1
H29A—C29—H29B107.9H49A—C49—H49B107.8
C29—C30—H30A109.5C49—C50—H50A109.5
C29—C30—H30B109.5C49—C50—H50B109.5
H30A—C30—H30B109.5H50A—C50—H50B109.5
C29—C30—H30C109.5C49—C50—H50C109.5
H30A—C30—H30C109.5H50A—C50—H50C109.5
H30B—C30—H30C109.5H50B—C50—H50C109.5
O11—S11—N11—C17176.1 (4)O31—S31—N31—C37174.0 (4)
O12—S11—N11—C1754.7 (5)O32—S31—N31—C3756.0 (5)
C14—S11—N11—C1761.3 (5)C34—S31—N31—C3759.6 (4)
C16—C11—C12—C130.9 (9)C36—C31—C32—C330.5 (8)
Cl11—C11—C12—C13179.7 (4)Cl31—C31—C32—C33178.3 (4)
C11—C12—C13—C140.8 (8)C31—C32—C33—C340.1 (9)
C12—C13—C14—C150.1 (8)C32—C33—C34—C350.7 (8)
C12—C13—C14—S11179.5 (4)C32—C33—C34—S31178.8 (4)
O11—S11—C14—C15143.6 (4)O31—S31—C34—C3336.7 (5)
O12—S11—C14—C1511.6 (5)O32—S31—C34—C33169.6 (4)
N11—S11—C14—C15106.1 (4)N31—S31—C34—C3374.1 (5)
O11—S11—C14—C1336.0 (5)O31—S31—C34—C35142.8 (4)
O12—S11—C14—C13168.0 (4)O32—S31—C34—C359.9 (5)
N11—S11—C14—C1374.3 (5)N31—S31—C34—C35106.4 (4)
C13—C14—C15—C160.9 (8)C33—C34—C35—C361.2 (8)
S11—C14—C15—C16178.7 (4)S31—C34—C35—C36178.3 (4)
C12—C11—C16—C150.2 (9)C34—C35—C36—C310.8 (8)
Cl11—C11—C16—C15179.6 (4)C32—C31—C36—C350.0 (8)
C14—C15—C16—C110.7 (8)Cl31—C31—C36—C35178.8 (4)
C18—N12—C17—O131.6 (8)C38—N32—C37—O333.5 (9)
C18—N12—C17—N11179.2 (4)C38—N32—C37—N31177.5 (5)
S11—N11—C17—O135.9 (7)S31—N31—C37—O3319.2 (7)
S11—N11—C17—N12171.8 (4)S31—N31—C37—N32159.9 (4)
C17—N12—C18—C1984.2 (6)C37—N32—C38—C3984.7 (6)
N12—C18—C19—C20179.7 (4)N32—C38—C39—C40177.7 (4)
O21—S21—N21—C27174.2 (4)O41—S41—N41—C47179.0 (4)
O22—S21—N21—C2756.4 (5)O42—S41—N41—C4751.5 (5)
C24—S21—N21—C2759.7 (4)C44—S41—N41—C4764.8 (5)
C26—C21—C22—C230.1 (8)C46—C41—C42—C431.0 (8)
Cl21—C21—C22—C23178.8 (4)Cl41—C41—C42—C43178.2 (4)
C21—C22—C23—C240.7 (9)C41—C42—C43—C440.3 (8)
C22—C23—C24—C250.3 (8)C42—C43—C44—C451.9 (8)
C22—C23—C24—S21177.3 (4)C42—C43—C44—S41178.5 (4)
O21—S21—C24—C25137.3 (4)O41—S41—C44—C45147.3 (4)
O22—S21—C24—C255.3 (5)O42—S41—C44—C4514.9 (5)
N21—S21—C24—C25112.0 (5)N41—S41—C44—C45102.7 (4)
O21—S21—C24—C2340.2 (5)O41—S41—C44—C4333.2 (5)
O22—S21—C24—C23172.2 (4)O42—S41—C44—C43165.6 (4)
N21—S21—C24—C2370.5 (5)N41—S41—C44—C4376.8 (4)
C23—C24—C25—C260.8 (8)C43—C44—C45—C462.1 (8)
S21—C24—C25—C26178.3 (4)S41—C44—C45—C46178.3 (4)
C24—C25—C26—C211.4 (9)C42—C41—C46—C450.8 (9)
C22—C21—C26—C250.9 (8)Cl41—C41—C46—C45178.5 (4)
Cl21—C21—C26—C25177.7 (4)C44—C45—C46—C410.8 (8)
C28—N22—C27—O234.5 (8)C48—N42—C47—O435.3 (8)
C28—N22—C27—N21176.4 (5)C48—N42—C47—N41177.9 (5)
S21—N21—C27—O2318.1 (7)S41—N41—C47—O430.7 (7)
S21—N21—C27—N22161.1 (4)S41—N41—C47—N42176.3 (4)
C27—N22—C28—C2986.6 (6)C47—N42—C48—C49107.6 (5)
N22—C28—C29—C30179.0 (4)N42—C48—C49—C5066.3 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N11—H11N···O23i0.881.902.744 (5)160
N12—H12N···O22i0.882.283.008 (5)140
N12—H12N···O23i0.882.573.295 (5)140
N21—H21N···O130.882.042.750 (5)137
N22—H22N···O120.882.313.027 (5)138
N22—H22N···O130.882.453.183 (5)141
N31—H31N···O430.882.062.725 (5)132
N32—H32N···O420.882.283.005 (5)140
N32—H32N···O430.882.533.237 (5)138
N41—H41N···O33i0.881.862.726 (5)170
N42—H42N···O32i0.882.222.994 (5)146
N42—H42N···O33i0.882.683.386 (5)139
Symmetry code: (i) x, y+1, z.

Experimental details

(bIICPA200K)(bIIICPA100K)
Crystal data
Chemical formulaC10H13ClN2O3SC10H13ClN2O3S
Mr276.73276.73
Crystal system, space groupMonoclinic, P2/cMonoclinic, P2/n
Temperature (K)200100
a, b, c (Å)14.5882 (5), 9.2584 (2), 19.1532 (6)28.4475 (12), 9.2322 (3), 19.2298 (7)
β (°) 93.260 (3) 95.562 (4)
V3)2582.71 (13)5026.6 (3)
Z816
Radiation typeMo KαMo Kα
µ (mm1)0.460.47
Crystal size (mm)0.32 × 0.20 × 0.080.22 × 0.15 × 0.06
Data collection
DiffractometerOxford Diffraction KM4 CCD
diffractometer
Oxford Diffraction KM4 CCD
diffractometer
Absorption correctionMulti-scan
CrysAlis RED (Oxford Diffraction, 2008)
Multi-scan
CrysAlis RED (Oxford Diffraction, 2008)
Tmin, Tmax0.899, 0.9650.946, 0.973
No. of measured, independent and
observed [I > 2σ(I)] reflections
53248, 7720, 2794 42040, 14436, 6814
Rint0.1110.087
(sin θ/λ)max1)0.6020.610
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.147, 0.75 0.053, 0.139, 0.81
No. of reflections772014436
No. of parameters310618
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.40, 0.300.37, 0.45

Computer programs: CrysAlis CCD (Oxford Diffraction,2008a), CrysAlis RED (Oxford Diffraction,2008b), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) for (bIICPA200K) top
D—H···AD—HH···AD···AD—H···A
N11—H11N···O23i0.882.002.737 (4)140.8
N12—H12N···O22i0.882.373.100 (5)140.7
N12—H12N···O23i0.882.553.271 (5)139.5
N21—H21N···O130.881.892.728 (4)158.9
N22—H22N···O120.882.363.086 (5)140.0
N22—H22N···O130.882.523.244 (5)139.8
Symmetry code: (i) x, y+1, z.
Hydrogen-bond geometry (Å, º) for (bIIICPA100K) top
D—H···AD—HH···AD···AD—H···A
N11—H11N···O23i0.881.902.744 (5)159.5
N12—H12N···O22i0.882.283.008 (5)139.8
N12—H12N···O23i0.882.573.295 (5)139.7
N21—H21N···O130.882.042.750 (5)137.2
N22—H22N···O120.882.313.027 (5)138.4
N22—H22N···O130.882.453.183 (5)140.7
N31—H31N···O430.882.062.725 (5)132.0
N32—H32N···O420.882.283.005 (5)140.1
N32—H32N···O430.882.533.237 (5)138.0
N41—H41N···O33i0.881.862.726 (5)169.6
N42—H42N···O32i0.882.222.994 (5)146.0
N42—H42N···O33i0.882.683.386 (5)138.5
Symmetry code: (i) x, y+1, z.
 

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