Solid-state transformations in the β-form of chlorpropamide on cooling to 100 K

Drebushchak, T.N.; Drebushchak, V.A.; Boldyreva, E.V.

doi:10.1107/S0108768111004290

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Solid-state transformations in the β-form of chlorpropamide on cooling to 100 K

T. N. Drebushchak, V. A. Drebushchak and E. V. Boldyreva

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]

β^II (P2/c, Z′ = 2) [if and only if]

β^III (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.

Keywords: polymorphism; chlorpropamide; molecular conformations; hydrogen bonds; twinning; phase transition.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S0108768111004290/gp5041sup1.cif Contains datablocks bIICPA200K, bIIICPA100K
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768111004290/gp5041bIICPA200Ksup2.hkl Contains datablock bIICPA200K
	Structure factor file (CIF format) https://doi.org/10.1107/S0108768111004290/gp5041bIIICPA100Ksup3.hkl Contains datablock bIIICPA100K
	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

(bIICPA200K) 4-chloro-N-((propylaminocarbonyl)benzenesulfonamide top

Crystal data top

C₁₀H₁₃ClN₂O₃S	F(000) = 1152
M_r = 276.73	D_x = 1.423 Mg m⁻³
Monoclinic, P2/c	Melting point: phase transition K
Hall symbol: -P 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 14.5882 (5) Å	Cell parameters from 13850 reflections
b = 9.2584 (2) Å	θ = 2.8–29.2°
c = 19.1532 (6) Å	µ = 0.46 mm⁻¹
β = 93.260 (3)°	T = 200 K
V = 2582.71 (13) Å³	Block, colourless
Z = 8	0.32 × 0.20 × 0.08 mm

Data collection top

Oxford Diffraction KM4 CCD diffractometer	7720 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2794 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.111
Detector resolution: 10.3457 pixels mm^-1	θ_max = 25.4°, θ_min = 2.8°
ω scans	h = −17→17
Absorption correction: multi-scan CrysAlis RED (Oxford Diffraction, 2008)	k = −11→11
T_min = 0.899, T_max = 0.965	l = −23→23
53248 measured 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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.147	H-atom parameters constrained
S = 0.75	w = 1/[σ²(F_o²) + (0.0498P)²] where P = (F_o² + 2F_c²)/3
7720 reflections	(Δ/σ)_max < 0.001
310 parameters	Δρ_max = 0.40 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

C₁₀H₁₃ClN₂O₃S	V = 2582.71 (13) Å³
M_r = 276.73	Z = 8
Monoclinic, P2/c	Mo Kα radiation
a = 14.5882 (5) Å	µ = 0.46 mm⁻¹
b = 9.2584 (2) Å	T = 200 K
c = 19.1532 (6) Å	0.32 × 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)
T_min = 0.899, T_max = 0.965	R_int = 0.111
53248 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.147	H-atom parameters constrained
S = 0.75	Δρ_max = 0.40 e Å⁻³
7720 reflections	Δρ_min = −0.30 e Å⁻³
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 (R_int = 0.051) and 53248 overlapped reflections (R_int = 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

	x	y	z	U_iso*/U_eq
Cl11	0.16683 (11)	0.51394 (16)	0.08137 (7)	0.0822 (5)
S11	0.10693 (8)	0.68692 (13)	0.39003 (6)	0.0501 (3)
O11	0.0449 (2)	0.8069 (3)	0.39041 (17)	0.0619 (9)
O12	0.0868 (2)	0.5584 (3)	0.42699 (16)	0.0599 (9)
O13	0.2854 (2)	0.5437 (3)	0.41974 (18)	0.0617 (10)
N11	0.2031 (2)	0.7548 (4)	0.42096 (19)	0.0426 (10)
H11N	0.2039	0.8447	0.4359	0.051*
N12	0.3607 (3)	0.7540 (4)	0.4347 (2)	0.0485 (10)
H12N	0.3551	0.8485	0.4363	0.058*
C11	0.1514 (3)	0.5624 (6)	0.1668 (2)	0.0613 (14)
C12	0.1423 (3)	0.7065 (6)	0.1842 (3)	0.0676 (15)
H12	0.1458	0.7791	0.1494	0.081*
C13	0.1281 (3)	0.7440 (5)	0.2523 (3)	0.0566 (14)
H13	0.1202	0.8427	0.2641	0.068*
C14	0.1253 (3)	0.6391 (4)	0.3036 (2)	0.0444 (12)
C15	0.1353 (3)	0.4973 (5)	0.2844 (2)	0.0541 (13)
H15	0.1336	0.4243	0.3192	0.065*
C16	0.1476 (3)	0.4575 (5)	0.2163 (3)	0.0620 (14)
H16	0.1535	0.3586	0.2041	0.074*
C17	0.2859 (3)	0.6754 (5)	0.4248 (2)	0.0471 (12)
C18	0.4529 (3)	0.6912 (6)	0.4433 (3)	0.0619 (14)
H18A	0.4488	0.5946	0.4650	0.074*
H18B	0.4915	0.7528	0.4754	0.074*
C19	0.4978 (3)	0.6773 (6)	0.3752 (3)	0.0706 (16)
H19A	0.5031	0.7740	0.3538	0.085*
H19B	0.4590	0.6167	0.3428	0.085*
C20	0.5937 (4)	0.6094 (6)	0.3851 (4)	0.111 (3)
H20A	0.6334	0.6721	0.4149	0.167*
H20B	0.6200	0.5980	0.3395	0.167*
H20C	0.5889	0.5145	0.4074	0.167*
Cl21	0.29708 (11)	0.00088 (16)	0.07013 (7)	0.0840 (5)
S21	0.40918 (8)	0.18721 (13)	0.37561 (7)	0.0515 (3)
O21	0.4698 (2)	0.3092 (3)	0.37311 (18)	0.0654 (10)
O22	0.4384 (2)	0.0617 (3)	0.41412 (16)	0.0596 (9)
O23	0.2360 (2)	0.0437 (3)	0.40534 (16)	0.0513 (8)
N21	0.3183 (3)	0.2551 (4)	0.40755 (19)	0.0490 (11)
H21N	0.3191	0.3468	0.4196	0.059*
N22	0.1671 (3)	0.2502 (4)	0.43610 (19)	0.0462 (10)
H22N	0.1732	0.3440	0.4420	0.055*
C21	0.3274 (3)	0.0540 (6)	0.1543 (2)	0.0541 (13)
C22	0.3401 (4)	0.1972 (6)	0.1706 (3)	0.0737 (16)
H22	0.3325	0.2683	0.1350	0.088*
C23	0.3636 (3)	0.2381 (5)	0.2377 (3)	0.0620 (15)
H23	0.3715	0.3376	0.2487	0.074*
C24	0.3761 (3)	0.1348 (5)	0.2900 (2)	0.0507 (12)
C25	0.3645 (3)	−0.0089 (5)	0.2732 (2)	0.0564 (13)
H25	0.3738	−0.0806	0.3084	0.068*
C26	0.3397 (3)	−0.0489 (5)	0.2062 (3)	0.0634 (14)
H26	0.3308	−0.1481	0.1952	0.076*
C27	0.2387 (3)	0.1749 (5)	0.4169 (2)	0.0434 (11)
C28	0.0792 (3)	0.1840 (5)	0.4479 (3)	0.0602 (14)
H28A	0.0491	0.2376	0.4850	0.072*
H28B	0.0890	0.0833	0.4640	0.072*
C29	0.0167 (3)	0.1846 (6)	0.3806 (4)	0.102 (3)
H29A	0.0079	0.2852	0.3640	0.122*
H29B	0.0465	0.1296	0.3437	0.122*
C30	−0.0709 (4)	0.1216 (6)	0.3924 (4)	0.135 (3)
H30A	−0.0621	0.0230	0.4102	0.202*
H30B	−0.1085	0.1191	0.3483	0.202*
H30C	−0.1020	0.1795	0.4267	0.202*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl11	0.1129 (12)	0.0893 (11)	0.0438 (8)	−0.0141 (9)	−0.0021 (8)	0.0033 (7)
S11	0.0575 (8)	0.0371 (6)	0.0563 (8)	−0.0031 (7)	0.0076 (6)	−0.0060 (7)
O11	0.058 (2)	0.0480 (18)	0.080 (3)	0.0100 (19)	0.0075 (18)	−0.0110 (19)
O12	0.087 (3)	0.0418 (19)	0.052 (2)	−0.0216 (18)	0.0179 (18)	0.0004 (16)
O13	0.070 (2)	0.0264 (18)	0.087 (3)	0.0053 (17)	−0.0103 (19)	−0.0054 (17)
N11	0.046 (2)	0.0283 (18)	0.055 (3)	−0.0020 (18)	0.010 (2)	−0.0101 (18)
N12	0.051 (3)	0.033 (2)	0.061 (3)	−0.001 (2)	0.002 (2)	−0.0052 (19)
C11	0.080 (4)	0.058 (3)	0.044 (3)	−0.015 (3)	−0.014 (3)	0.004 (3)
C12	0.090 (4)	0.058 (4)	0.055 (4)	−0.003 (3)	0.009 (3)	0.027 (3)
C13	0.072 (4)	0.036 (3)	0.062 (4)	0.010 (2)	0.009 (3)	0.008 (3)
C14	0.045 (3)	0.032 (3)	0.055 (3)	−0.003 (2)	−0.003 (2)	0.004 (2)
C15	0.089 (4)	0.034 (3)	0.039 (3)	−0.014 (2)	−0.002 (3)	0.006 (2)
C16	0.092 (4)	0.041 (3)	0.051 (3)	−0.010 (3)	−0.008 (3)	−0.002 (3)
C17	0.061 (3)	0.032 (3)	0.048 (3)	−0.002 (3)	0.004 (2)	−0.002 (2)
C18	0.066 (4)	0.060 (3)	0.057 (4)	−0.014 (3)	−0.018 (3)	−0.007 (3)
C19	0.056 (3)	0.050 (3)	0.107 (5)	0.014 (3)	0.015 (3)	0.017 (3)
C20	0.078 (4)	0.061 (4)	0.197 (8)	0.014 (4)	0.027 (5)	0.023 (5)
Cl21	0.1168 (13)	0.0887 (11)	0.0458 (8)	−0.0056 (9)	−0.0026 (8)	0.0015 (8)
S21	0.0551 (8)	0.0379 (6)	0.0613 (9)	−0.0028 (7)	0.0007 (7)	−0.0058 (7)
O21	0.065 (2)	0.0487 (19)	0.083 (3)	−0.0164 (19)	0.0044 (18)	−0.0142 (19)
O22	0.074 (2)	0.0419 (19)	0.060 (2)	0.0137 (17)	−0.0188 (18)	−0.0102 (16)
O23	0.062 (2)	0.0283 (17)	0.065 (2)	−0.0020 (16)	0.0150 (17)	−0.0022 (16)
N21	0.060 (3)	0.0314 (19)	0.055 (3)	0.003 (2)	−0.001 (2)	−0.0119 (19)
N22	0.057 (3)	0.036 (2)	0.046 (3)	0.005 (2)	0.007 (2)	0.0003 (19)
C21	0.059 (3)	0.063 (3)	0.040 (3)	−0.007 (3)	0.009 (2)	0.003 (3)
C22	0.116 (5)	0.050 (3)	0.055 (4)	−0.006 (3)	0.008 (3)	0.008 (3)
C23	0.080 (4)	0.033 (3)	0.075 (4)	−0.011 (3)	0.015 (3)	0.002 (3)
C24	0.052 (3)	0.041 (3)	0.059 (3)	0.003 (2)	0.003 (2)	0.005 (2)
C25	0.082 (4)	0.034 (3)	0.054 (3)	0.009 (3)	0.005 (3)	0.003 (2)
C26	0.087 (4)	0.046 (3)	0.058 (4)	0.002 (3)	0.016 (3)	−0.004 (3)
C27	0.060 (3)	0.032 (3)	0.039 (3)	0.006 (3)	0.008 (2)	0.006 (2)
C28	0.070 (4)	0.043 (3)	0.070 (4)	0.010 (3)	0.021 (3)	0.004 (3)
C29	0.044 (3)	0.063 (4)	0.195 (8)	−0.017 (3)	−0.028 (4)	0.078 (4)
C30	0.130 (6)	0.069 (5)	0.201 (9)	0.024 (5)	−0.011 (6)	0.032 (5)

Geometric parameters (Å, º) top

Cl11—C11	1.723 (5)	Cl21—C21	1.719 (5)
S11—O12	1.424 (3)	S21—O22	1.428 (3)
S11—O11	1.433 (3)	S21—O21	1.437 (3)
S11—N11	1.619 (4)	S21—N21	1.618 (4)
S11—C14	1.748 (5)	S21—C24	1.752 (5)
O13—C17	1.223 (5)	O23—C27	1.235 (5)
N11—C17	1.412 (5)	N21—C27	1.399 (5)
N11—H11N	0.8800	N21—H21N	0.8800
N12—C17	1.316 (5)	N22—C27	1.324 (5)
N12—C18	1.466 (5)	N22—C28	1.450 (5)
N12—H12N	0.8800	N22—H22N	0.8800
C11—C16	1.361 (6)	C21—C22	1.372 (7)
C11—C12	1.384 (7)	C21—C26	1.381 (6)
C12—C13	1.375 (7)	C22—C23	1.365 (6)
C12—H12	0.9500	C22—H22	0.9500
C13—C14	1.385 (6)	C23—C24	1.389 (6)
C13—H13	0.9500	C23—H23	0.9500
C14—C15	1.374 (6)	C24—C25	1.377 (6)
C15—C16	1.377 (6)	C25—C26	1.364 (6)
C15—H15	0.9500	C25—H25	0.9500
C16—H16	0.9500	C26—H26	0.9500
C18—C19	1.498 (7)	C28—C29	1.536 (7)
C18—H18A	0.9900	C28—H28A	0.9900
C18—H18B	0.9900	C28—H28B	0.9900
C19—C20	1.535 (6)	C29—C30	1.436 (7)
C19—H19A	0.9900	C29—H29A	0.9900
C19—H19B	0.9900	C29—H29B	0.9900
C20—H20A	0.9800	C30—H30A	0.9800
C20—H20B	0.9800	C30—H30B	0.9800
C20—H20C	0.9800	C30—H30C	0.9800

O12—S11—O11	119.8 (2)	O22—S21—O21	119.38 (19)
O12—S11—N11	110.0 (2)	O22—S21—N21	110.3 (2)
O11—S11—N11	103.38 (19)	O21—S21—N21	103.1 (2)
O12—S11—C14	107.83 (19)	O22—S21—C24	108.5 (2)
O11—S11—C14	109.4 (2)	O21—S21—C24	108.9 (2)
N11—S11—C14	105.6 (2)	N21—S21—C24	105.9 (2)
C17—N11—S11	122.5 (3)	C27—N21—S21	123.1 (3)
C17—N11—H11N	118.7	C27—N21—H21N	118.4
S11—N11—H11N	118.7	S21—N21—H21N	118.4
C17—N12—C18	123.0 (4)	C27—N22—C28	122.6 (4)
C17—N12—H12N	118.5	C27—N22—H22N	118.7
C18—N12—H12N	118.5	C28—N22—H22N	118.7
C16—C11—C12	120.8 (5)	C22—C21—C26	119.5 (5)
C16—C11—Cl11	119.2 (4)	C22—C21—Cl21	120.9 (4)
C12—C11—Cl11	120.0 (4)	C26—C21—Cl21	119.6 (4)
C13—C12—C11	119.6 (4)	C23—C22—C21	120.4 (5)
C13—C12—H12	120.2	C23—C22—H22	119.8
C11—C12—H12	120.2	C21—C22—H22	119.8
C12—C13—C14	120.5 (4)	C22—C23—C24	120.2 (4)
C12—C13—H13	119.7	C22—C23—H23	119.9
C14—C13—H13	119.7	C24—C23—H23	119.9
C15—C14—C13	118.1 (4)	C25—C24—C23	119.2 (5)
C15—C14—S11	121.3 (3)	C25—C24—S21	120.6 (4)
C13—C14—S11	120.5 (3)	C23—C24—S21	120.1 (4)
C14—C15—C16	122.1 (4)	C26—C25—C24	120.2 (5)
C14—C15—H15	119.0	C26—C25—H25	119.9
C16—C15—H15	119.0	C24—C25—H25	119.9
C11—C16—C15	118.8 (5)	C25—C26—C21	120.5 (5)
C11—C16—H16	120.6	C25—C26—H26	119.8
C15—C16—H16	120.6	C21—C26—H26	119.8
O13—C17—N12	124.3 (5)	O23—C27—N22	123.4 (4)
O13—C17—N11	120.9 (4)	O23—C27—N21	121.1 (4)
N12—C17—N11	114.8 (4)	N22—C27—N21	115.5 (4)
N12—C18—C19	112.4 (4)	N22—C28—C29	110.9 (4)
N12—C18—H18A	109.1	N22—C28—H28A	109.5
C19—C18—H18A	109.1	C29—C28—H28A	109.5
N12—C18—H18B	109.1	N22—C28—H28B	109.5
C19—C18—H18B	109.1	C29—C28—H28B	109.5
H18A—C18—H18B	107.9	H28A—C28—H28B	108.1
C18—C19—C20	111.6 (5)	C30—C29—C28	111.0 (5)
C18—C19—H19A	109.3	C30—C29—H29A	109.4
C20—C19—H19A	109.3	C28—C29—H29A	109.4
C18—C19—H19B	109.3	C30—C29—H29B	109.4
C20—C19—H19B	109.3	C28—C29—H29B	109.4
H19A—C19—H19B	108.0	H29A—C29—H29B	108.0
C19—C20—H20A	109.5	C29—C30—H30A	109.5
C19—C20—H20B	109.5	C29—C30—H30B	109.5
H20A—C20—H20B	109.5	H30A—C30—H30B	109.5
C19—C20—H20C	109.5	C29—C30—H30C	109.5
H20A—C20—H20C	109.5	H30A—C30—H30C	109.5
H20B—C20—H20C	109.5	H30B—C30—H30C	109.5

O12—S11—N11—C17	55.8 (4)	O22—S21—N21—C27	−54.0 (4)
O11—S11—N11—C17	−175.1 (4)	O21—S21—N21—C27	177.5 (4)
C14—S11—N11—C17	−60.3 (4)	C24—S21—N21—C27	63.2 (4)
C16—C11—C12—C13	−0.9 (8)	C26—C21—C22—C23	−0.7 (8)
Cl11—C11—C12—C13	178.7 (4)	Cl21—C21—C22—C23	179.6 (4)
C11—C12—C13—C14	1.7 (8)	C21—C22—C23—C24	0.8 (8)
C12—C13—C14—C15	−1.2 (7)	C22—C23—C24—C25	0.1 (8)
C12—C13—C14—S11	−179.8 (4)	C22—C23—C24—S21	178.3 (4)
O12—S11—C14—C15	−11.5 (4)	O22—S21—C24—C25	12.1 (5)
O11—S11—C14—C15	−143.3 (4)	O21—S21—C24—C25	143.5 (4)
N11—S11—C14—C15	106.0 (4)	N21—S21—C24—C25	−106.3 (4)
O12—S11—C14—C13	167.0 (4)	O22—S21—C24—C23	−166.1 (4)
O11—S11—C14—C13	35.2 (4)	O21—S21—C24—C23	−34.7 (5)
N11—S11—C14—C13	−75.4 (4)	N21—S21—C24—C23	75.5 (4)
C13—C14—C15—C16	−0.1 (7)	C23—C24—C25—C26	−1.0 (8)
S11—C14—C15—C16	178.5 (4)	S21—C24—C25—C26	−179.3 (4)
C12—C11—C16—C15	−0.4 (8)	C24—C25—C26—C21	1.1 (8)
Cl11—C11—C16—C15	180.0 (4)	C22—C21—C26—C25	−0.2 (8)
C14—C15—C16—C11	0.9 (8)	Cl21—C21—C26—C25	179.5 (4)
C18—N12—C17—O13	−2.2 (8)	C28—N22—C27—O23	2.3 (7)
C18—N12—C17—N11	177.2 (4)	C28—N22—C27—N21	179.8 (4)
S11—N11—C17—O13	−16.5 (7)	S21—N21—C27—O23	5.0 (6)
S11—N11—C17—N12	164.1 (3)	S21—N21—C27—N22	−172.6 (3)
C17—N12—C18—C19	91.5 (6)	C27—N22—C28—C29	−91.2 (6)
N12—C18—C19—C20	−179.2 (4)	N22—C28—C29—C30	−179.0 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11N···O23ⁱ	0.88	2.00	2.737 (4)	141
N12—H12N···O22ⁱ	0.88	2.37	3.100 (5)	141
N12—H12N···O23ⁱ	0.88	2.55	3.271 (5)	140
N21—H21N···O13	0.88	1.89	2.728 (4)	159
N22—H22N···O12	0.88	2.36	3.086 (5)	140
N22—H22N···O13	0.88	2.52	3.244 (5)	140

Symmetry code: (i) x, y+1, z.

(bIIICPA100K) 4-chloro-N-((propylaminocarbonyl)benzenesulfonamide top

Crystal data top

C₁₀H₁₃ClN₂O₃S	F(000) = 2304
M_r = 276.73	D_x = 1.463 Mg m⁻³
Monoclinic, P2/n	Melting point: phase transition K
Hall symbol: -P 2yac	Mo Kα radiation, λ = 0.71073 Å
a = 28.4475 (12) Å	Cell parameters from 9693 reflections
b = 9.2322 (3) Å	θ = 3.1–29.3°
c = 19.2298 (7) Å	µ = 0.47 mm⁻¹
β = 95.562 (4)°	T = 100 K
V = 5026.6 (3) Å³	Block, colourless
Z = 16	0.22 × 0.15 × 0.06 mm

Data collection top

Oxford Diffraction KM4 CCD diffractometer	14436 independent reflections
Radiation source: Enhance (Mo) X-ray Source	6814 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.087
Detector resolution: 10.3457 pixels mm^-1	θ_max = 25.7°, θ_min = 3.1°
ω scans	h = −33→34
Absorption correction: multi-scan CrysAlis RED (Oxford Diffraction, 2008)	k = −11→11
T_min = 0.946, T_max = 0.973	l = −23→23
42040 measured 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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.139	H-atom parameters constrained
S = 0.81	w = 1/[σ²(F_o²) + (0.0519P)²] where P = (F_o² + 2F_c²)/3
14436 reflections	(Δ/σ)_max < 0.001
618 parameters	Δρ_max = 0.37 e Å⁻³
0 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

C₁₀H₁₃ClN₂O₃S	V = 5026.6 (3) Å³
M_r = 276.73	Z = 16
Monoclinic, P2/n	Mo Kα radiation
a = 28.4475 (12) Å	µ = 0.47 mm⁻¹
b = 9.2322 (3) Å	T = 100 K
c = 19.2298 (7) Å	0.22 × 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)
T_min = 0.946, T_max = 0.973	R_int = 0.087
42040 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.139	H-atom parameters constrained
S = 0.81	Δρ_max = 0.37 e Å⁻³
14436 reflections	Δρ_min = −0.45 e Å⁻³
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 (R_int = 0.065) and 42040 overlapped reflections (R_int = 0.087) of component 1. Twin component ratio 0.56:0.44.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
S11	0.21089 (5)	0.71308 (13)	0.37489 (8)	0.0205 (3)
Cl11	0.13654 (5)	0.52901 (15)	0.07238 (8)	0.0360 (4)
O11	0.24094 (12)	0.8357 (3)	0.3716 (2)	0.0278 (9)
O12	0.22796 (12)	0.5854 (3)	0.4118 (2)	0.0233 (9)
O13	0.12415 (11)	0.5664 (3)	0.40638 (19)	0.0197 (9)
N11	0.16538 (14)	0.7787 (4)	0.4097 (2)	0.0191 (10)
H11N	0.1662	0.8698	0.4231	0.023*
N12	0.08929 (15)	0.7716 (4)	0.4398 (2)	0.0203 (10)
H12N	0.0928	0.8653	0.4468	0.024*
C11	0.15720 (19)	0.5804 (5)	0.1573 (3)	0.0222 (13)
C12	0.1624 (2)	0.7259 (5)	0.1722 (3)	0.0321 (15)
H12	0.1547	0.7970	0.1372	0.039*
C13	0.17886 (19)	0.7655 (6)	0.2390 (3)	0.0259 (14)
H13	0.1830	0.8652	0.2502	0.031*
C14	0.18954 (18)	0.6611 (5)	0.2905 (3)	0.0219 (13)
C15	0.18325 (18)	0.5164 (5)	0.2737 (3)	0.0207 (13)
H15	0.1900	0.4444	0.3086	0.025*
C16	0.1671 (2)	0.4761 (5)	0.2060 (3)	0.0255 (13)
H16	0.1631	0.3767	0.1940	0.031*
C17	0.12480 (18)	0.6968 (5)	0.4193 (3)	0.0165 (12)
C18	0.04397 (19)	0.7037 (5)	0.4516 (3)	0.0263 (14)
H18A	0.0282	0.7626	0.4855	0.032*
H18B	0.0500	0.6064	0.4722	0.032*
C19	0.01092 (19)	0.6890 (5)	0.3837 (3)	0.0292 (15)
H19A	0.0046	0.7861	0.3632	0.035*
H19B	0.0266	0.6302	0.3497	0.035*
C20	−0.03458 (18)	0.6193 (6)	0.3969 (3)	0.0314 (14)
H20A	−0.0288	0.5185	0.4113	0.047*
H20B	−0.0563	0.6218	0.3541	0.047*
H20C	−0.0486	0.6717	0.4341	0.047*
S21	0.05747 (5)	0.20420 (13)	0.39707 (7)	0.0193 (3)
Cl21	0.07533 (5)	0.03885 (14)	0.08621 (7)	0.0272 (3)
O21	0.02457 (12)	0.3210 (3)	0.39749 (19)	0.0235 (9)
O22	0.04981 (13)	0.0740 (3)	0.43476 (18)	0.0232 (9)
O23	0.15094 (13)	0.0702 (3)	0.4252 (2)	0.0275 (10)
N21	0.10740 (14)	0.2770 (4)	0.4269 (2)	0.0187 (10)
H21N	0.1075	0.3669	0.4422	0.022*
N22	0.18848 (15)	0.2866 (4)	0.4349 (2)	0.0219 (11)
H22N	0.1849	0.3813	0.4344	0.026*
C21	0.07206 (17)	0.0859 (6)	0.1726 (3)	0.0213 (13)
C22	0.07025 (19)	0.2306 (5)	0.1914 (3)	0.0275 (14)
H22	0.0714	0.3042	0.1571	0.033*
C23	0.06678 (19)	0.2662 (5)	0.2593 (3)	0.0257 (14)
H23	0.0659	0.3652	0.2726	0.031*
C24	0.06450 (18)	0.1570 (5)	0.3101 (3)	0.0190 (12)
C25	0.06601 (19)	0.0134 (5)	0.2904 (3)	0.0251 (14)
H25	0.0641	−0.0609	0.3242	0.030*
C26	0.07030 (19)	−0.0222 (5)	0.2218 (3)	0.0239 (13)
H26	0.0720	−0.1209	0.2084	0.029*
C27	0.14990 (19)	0.2019 (5)	0.4291 (3)	0.0182 (12)
C28	0.23616 (19)	0.2271 (5)	0.4420 (3)	0.0275 (14)
H28A	0.2364	0.1367	0.4698	0.033*
H28B	0.2577	0.2969	0.4680	0.033*
C29	0.2547 (2)	0.1944 (5)	0.3719 (3)	0.0289 (14)
H29A	0.2551	0.2849	0.3444	0.035*
H29B	0.2330	0.1255	0.3455	0.035*
C30	0.30442 (19)	0.1297 (5)	0.3811 (3)	0.0338 (16)
H30A	0.3264	0.2006	0.4040	0.051*
H30B	0.3144	0.1048	0.3352	0.051*
H30C	0.3043	0.0421	0.4099	0.051*
S31	0.55663 (5)	0.15921 (12)	0.40022 (7)	0.0174 (3)
Cl31	0.57454 (5)	0.00535 (14)	0.08763 (7)	0.0278 (3)
O31	0.52418 (12)	0.2755 (3)	0.40220 (19)	0.0228 (9)
O32	0.54986 (12)	0.0270 (3)	0.43614 (18)	0.0195 (8)
O33	0.64992 (13)	0.0231 (3)	0.4279 (2)	0.0294 (10)
N31	0.60691 (14)	0.2305 (4)	0.4314 (2)	0.0161 (10)
H31N	0.6070	0.3193	0.4479	0.019*
N32	0.68793 (15)	0.2388 (4)	0.4386 (2)	0.0228 (11)
H32N	0.6842	0.3334	0.4394	0.027*
C31	0.57098 (18)	0.0495 (5)	0.1742 (3)	0.0200 (12)
C32	0.56652 (19)	0.1927 (5)	0.1936 (3)	0.0261 (14)
H32	0.5663	0.2673	0.1595	0.031*
C33	0.5624 (2)	0.2267 (5)	0.2626 (3)	0.0248 (13)
H33	0.5593	0.3250	0.2761	0.030*
C34	0.56294 (17)	0.1169 (5)	0.3128 (3)	0.0167 (12)
C35	0.56814 (18)	−0.0276 (5)	0.2926 (3)	0.0220 (13)
H35	0.5691	−0.1029	0.3264	0.026*
C36	0.57180 (19)	−0.0596 (5)	0.2233 (3)	0.0230 (13)
H36	0.5749	−0.1575	0.2093	0.028*
C37	0.6501 (2)	0.1558 (5)	0.4328 (3)	0.0195 (13)
C38	0.73638 (19)	0.1797 (6)	0.4439 (3)	0.0267 (14)
H38A	0.7374	0.0895	0.4718	0.032*
H38B	0.7582	0.2502	0.4687	0.032*
C39	0.75302 (19)	0.1477 (5)	0.3733 (3)	0.0279 (14)
H39A	0.7534	0.2385	0.3460	0.034*
H39B	0.7307	0.0800	0.3475	0.034*
C40	0.80181 (19)	0.0818 (6)	0.3804 (3)	0.0339 (15)
H40A	0.8238	0.1476	0.4069	0.051*
H40B	0.8122	0.0660	0.3338	0.051*
H40C	0.8011	−0.0110	0.4050	0.051*
S41	0.70684 (5)	0.66682 (13)	0.37669 (8)	0.0204 (3)
Cl41	0.64736 (5)	0.47530 (14)	0.07030 (7)	0.0308 (3)
O41	0.73630 (12)	0.7908 (3)	0.3747 (2)	0.0250 (9)
O42	0.72302 (12)	0.5403 (3)	0.41542 (18)	0.0227 (9)
O43	0.62015 (12)	0.5163 (3)	0.40394 (19)	0.0200 (8)
N41	0.65923 (15)	0.7324 (4)	0.4084 (2)	0.0209 (11)
H41N	0.6587	0.8249	0.4194	0.025*
N42	0.58415 (14)	0.7202 (4)	0.4404 (2)	0.0171 (10)
H42N	0.5868	0.8147	0.4457	0.021*
C41	0.66228 (18)	0.5311 (5)	0.1555 (3)	0.0239 (13)
C42	0.66840 (19)	0.6751 (5)	0.1707 (3)	0.0246 (14)
H42	0.6636	0.7458	0.1348	0.030*
C43	0.68154 (18)	0.7163 (6)	0.2385 (3)	0.0257 (14)
H43	0.6857	0.8160	0.2497	0.031*
C44	0.68874 (18)	0.6126 (5)	0.2907 (3)	0.0197 (13)
C45	0.68143 (19)	0.4673 (5)	0.2756 (3)	0.0241 (13)
H45	0.6853	0.3967	0.3116	0.029*
C46	0.66819 (19)	0.4259 (6)	0.2062 (3)	0.0251 (13)
H46	0.6634	0.3267	0.1945	0.030*
C47	0.62023 (19)	0.6481 (5)	0.4184 (3)	0.0182 (13)
C48	0.53991 (18)	0.6507 (5)	0.4565 (3)	0.0270 (14)
H48A	0.5319	0.6847	0.5027	0.032*
H48B	0.5448	0.5446	0.4595	0.032*
C49	0.49769 (19)	0.6831 (6)	0.4011 (3)	0.0270 (14)
H49A	0.4683	0.6447	0.4179	0.032*
H49B	0.4941	0.7893	0.3958	0.032*
C50	0.5041 (2)	0.6170 (6)	0.3305 (3)	0.0420 (17)
H50A	0.5357	0.6402	0.3175	0.063*
H50B	0.4803	0.6565	0.2953	0.063*
H50C	0.5005	0.5116	0.3330	0.063*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S11	0.0188 (8)	0.0172 (7)	0.0255 (9)	−0.0025 (6)	0.0024 (7)	−0.0019 (6)
Cl11	0.0467 (10)	0.0399 (8)	0.0204 (9)	−0.0005 (7)	−0.0019 (7)	0.0022 (6)
O11	0.019 (2)	0.023 (2)	0.041 (3)	−0.0066 (16)	0.0037 (19)	−0.0063 (17)
O12	0.020 (2)	0.0202 (19)	0.028 (2)	0.0028 (15)	−0.0061 (18)	−0.0012 (16)
O13	0.017 (2)	0.0110 (18)	0.032 (2)	−0.0047 (14)	0.0064 (17)	−0.0025 (15)
N11	0.019 (3)	0.009 (2)	0.030 (3)	−0.0004 (18)	0.007 (2)	0.0010 (18)
N12	0.023 (3)	0.011 (2)	0.027 (3)	−0.0008 (19)	0.005 (2)	−0.0015 (18)
C11	0.022 (3)	0.029 (3)	0.015 (3)	0.000 (2)	0.001 (2)	−0.001 (2)
C12	0.049 (4)	0.021 (3)	0.026 (4)	0.008 (3)	0.002 (3)	0.010 (3)
C13	0.038 (4)	0.018 (3)	0.022 (4)	−0.006 (2)	0.002 (3)	0.002 (2)
C14	0.015 (3)	0.024 (3)	0.026 (4)	−0.005 (2)	0.000 (2)	0.005 (2)
C15	0.026 (3)	0.014 (3)	0.022 (4)	0.003 (2)	0.004 (2)	−0.001 (2)
C16	0.038 (4)	0.010 (3)	0.027 (4)	0.004 (2)	−0.003 (3)	0.000 (2)
C17	0.011 (3)	0.020 (3)	0.019 (3)	0.000 (2)	0.002 (2)	0.006 (2)
C18	0.033 (4)	0.017 (3)	0.031 (4)	−0.003 (2)	0.015 (3)	−0.001 (2)
C19	0.037 (4)	0.014 (3)	0.035 (4)	−0.002 (2)	−0.004 (3)	0.008 (2)
C20	0.028 (3)	0.027 (3)	0.040 (4)	−0.004 (3)	0.007 (3)	0.016 (3)
S21	0.0207 (8)	0.0165 (7)	0.0211 (8)	0.0005 (6)	0.0048 (6)	−0.0010 (5)
Cl21	0.0282 (8)	0.0346 (7)	0.0190 (9)	−0.0037 (6)	0.0026 (6)	0.0005 (6)
O21	0.022 (2)	0.0231 (19)	0.025 (2)	0.0023 (16)	0.0016 (18)	0.0015 (16)
O22	0.034 (2)	0.0201 (19)	0.016 (2)	−0.0035 (16)	0.0063 (18)	0.0020 (15)
O23	0.031 (2)	0.0114 (19)	0.041 (3)	0.0053 (16)	0.005 (2)	0.0032 (16)
N21	0.019 (2)	0.014 (2)	0.024 (3)	−0.0010 (18)	0.008 (2)	−0.0095 (18)
N22	0.025 (3)	0.011 (2)	0.028 (3)	0.0015 (19)	−0.004 (2)	−0.0011 (18)
C21	0.010 (3)	0.035 (3)	0.017 (3)	−0.008 (2)	−0.004 (2)	0.000 (2)
C22	0.035 (4)	0.023 (3)	0.023 (4)	−0.004 (2)	−0.007 (3)	0.010 (2)
C23	0.036 (4)	0.012 (3)	0.028 (4)	−0.001 (2)	−0.002 (3)	0.003 (2)
C24	0.023 (3)	0.016 (3)	0.019 (3)	0.000 (2)	0.006 (2)	0.000 (2)
C25	0.032 (3)	0.019 (3)	0.024 (4)	−0.004 (2)	0.003 (3)	0.005 (2)
C26	0.032 (3)	0.018 (3)	0.021 (4)	−0.003 (2)	0.003 (3)	0.001 (2)
C27	0.026 (3)	0.017 (3)	0.013 (3)	0.004 (2)	0.004 (3)	−0.004 (2)
C28	0.030 (4)	0.020 (3)	0.031 (4)	0.002 (2)	−0.009 (3)	0.000 (2)
C29	0.036 (4)	0.018 (3)	0.033 (4)	0.002 (2)	0.002 (3)	0.000 (2)
C30	0.027 (4)	0.020 (3)	0.055 (5)	0.007 (2)	0.006 (3)	−0.005 (3)
S31	0.0208 (8)	0.0145 (7)	0.0174 (8)	−0.0003 (6)	0.0045 (6)	−0.0009 (5)
Cl31	0.0303 (8)	0.0346 (8)	0.0185 (9)	−0.0047 (6)	0.0015 (6)	−0.0011 (6)
O31	0.022 (2)	0.0186 (18)	0.029 (2)	0.0009 (15)	0.0092 (18)	−0.0006 (16)
O32	0.031 (2)	0.0142 (17)	0.013 (2)	−0.0047 (15)	0.0032 (17)	−0.0019 (14)
O33	0.029 (2)	0.0139 (19)	0.045 (3)	0.0059 (16)	0.004 (2)	−0.0055 (16)
N31	0.019 (2)	0.008 (2)	0.023 (3)	−0.0001 (17)	0.007 (2)	−0.0055 (17)
N32	0.024 (3)	0.013 (2)	0.031 (3)	−0.003 (2)	0.001 (2)	0.0028 (19)
C31	0.018 (3)	0.023 (3)	0.018 (3)	−0.003 (2)	0.000 (2)	−0.003 (2)
C32	0.030 (4)	0.024 (3)	0.025 (4)	−0.001 (2)	0.006 (3)	0.006 (2)
C33	0.033 (3)	0.018 (3)	0.024 (4)	0.002 (2)	0.003 (3)	−0.005 (2)
C34	0.010 (3)	0.018 (3)	0.023 (3)	0.000 (2)	0.005 (2)	−0.001 (2)
C35	0.027 (3)	0.018 (3)	0.021 (4)	−0.001 (2)	0.004 (3)	0.009 (2)
C36	0.031 (3)	0.019 (3)	0.018 (3)	−0.001 (2)	0.001 (3)	−0.007 (2)
C37	0.036 (4)	0.008 (3)	0.014 (3)	0.006 (2)	−0.004 (3)	0.004 (2)
C38	0.023 (3)	0.026 (3)	0.029 (4)	0.000 (2)	−0.006 (3)	−0.001 (2)
C39	0.029 (3)	0.018 (3)	0.035 (4)	−0.002 (2)	−0.006 (3)	−0.004 (2)
C40	0.031 (4)	0.021 (3)	0.050 (4)	0.003 (3)	0.002 (3)	−0.001 (3)
S41	0.0211 (8)	0.0150 (7)	0.0255 (9)	−0.0013 (6)	0.0035 (7)	−0.0021 (6)
Cl41	0.0344 (8)	0.0356 (8)	0.0216 (8)	0.0041 (6)	−0.0005 (7)	−0.0020 (6)
O41	0.016 (2)	0.0220 (19)	0.038 (3)	−0.0054 (15)	0.0053 (18)	−0.0016 (17)
O42	0.021 (2)	0.0264 (19)	0.019 (2)	0.0035 (16)	−0.0101 (17)	−0.0037 (15)
O43	0.025 (2)	0.0149 (19)	0.020 (2)	0.0005 (15)	0.0014 (17)	−0.0020 (15)
N41	0.031 (3)	0.009 (2)	0.025 (3)	−0.0031 (19)	0.012 (2)	−0.0061 (18)
N42	0.017 (2)	0.013 (2)	0.022 (3)	0.0042 (18)	0.001 (2)	−0.0008 (18)
C41	0.019 (3)	0.029 (3)	0.023 (3)	0.000 (2)	−0.003 (3)	0.000 (2)
C42	0.030 (3)	0.016 (3)	0.029 (4)	0.001 (2)	0.013 (3)	0.012 (2)
C43	0.032 (4)	0.017 (3)	0.029 (4)	−0.001 (2)	0.007 (3)	−0.001 (2)
C44	0.018 (3)	0.019 (3)	0.023 (4)	0.004 (2)	0.004 (2)	0.000 (2)
C45	0.035 (4)	0.015 (3)	0.024 (4)	0.002 (2)	0.008 (3)	0.005 (2)
C46	0.031 (3)	0.024 (3)	0.019 (3)	−0.001 (2)	0.000 (3)	−0.010 (2)
C47	0.028 (3)	0.011 (3)	0.016 (3)	−0.002 (2)	0.005 (3)	0.006 (2)
C48	0.025 (3)	0.026 (3)	0.032 (4)	0.001 (2)	0.012 (3)	−0.009 (2)
C49	0.022 (3)	0.031 (3)	0.025 (3)	0.006 (2)	−0.009 (3)	−0.002 (3)
C50	0.051 (4)	0.027 (3)	0.045 (4)	0.005 (3)	−0.007 (3)	−0.003 (3)

Geometric parameters (Å, º) top

S11—O11	1.424 (3)	S31—O31	1.419 (3)
S11—O12	1.436 (4)	S31—O32	1.425 (3)
S11—N11	1.630 (4)	S31—N31	1.634 (4)
S11—C14	1.743 (6)	S31—C34	1.753 (5)
Cl11—C11	1.746 (5)	Cl31—C31	1.727 (5)
O13—C17	1.229 (5)	O33—C37	1.229 (5)
N11—C17	1.407 (6)	N31—C37	1.406 (6)
N11—H11N	0.8800	N31—H31N	0.8800
N12—C17	1.315 (6)	N32—C37	1.317 (6)
N12—C18	1.470 (6)	N32—C38	1.477 (6)
N12—H12N	0.8800	N32—H32N	0.8800
C11—C16	1.355 (7)	C31—C36	1.379 (7)
C11—C12	1.379 (7)	C31—C32	1.382 (7)
C12—C13	1.373 (8)	C32—C33	1.380 (8)
C12—H12	0.9500	C32—H32	0.9500
C13—C14	1.395 (7)	C33—C34	1.399 (7)
C13—H13	0.9500	C33—H33	0.9500
C14—C15	1.382 (7)	C34—C35	1.401 (7)
C15—C16	1.389 (8)	C35—C36	1.378 (7)
C15—H15	0.9500	C35—H35	0.9500
C16—H16	0.9500	C36—H36	0.9500
C18—C19	1.538 (7)	C38—C39	1.509 (8)
C18—H18A	0.9900	C38—H38A	0.9900
C18—H18B	0.9900	C38—H38B	0.9900
C19—C20	1.489 (7)	C39—C40	1.509 (7)
C19—H19A	0.9900	C39—H39A	0.9900
C19—H19B	0.9900	C39—H39B	0.9900
C20—H20A	0.9800	C40—H40A	0.9800
C20—H20B	0.9800	C40—H40B	0.9800
C20—H20C	0.9800	C40—H40C	0.9800
S21—O21	1.428 (3)	S41—O41	1.421 (3)
S21—O22	1.431 (3)	S41—O42	1.437 (4)
S21—N21	1.625 (4)	S41—N41	1.653 (4)
S21—C24	1.759 (5)	S41—C44	1.756 (6)
Cl21—C21	1.728 (5)	Cl41—C41	1.730 (6)
O23—C27	1.219 (5)	O43—C47	1.248 (5)
N21—C27	1.391 (6)	N41—C47	1.384 (6)
N21—H21N	0.8800	N41—H41N	0.8800
N22—C27	1.343 (6)	N42—C47	1.327 (6)
N22—C28	1.458 (6)	N42—C48	1.472 (6)
N22—H22N	0.8800	N42—H42N	0.8800
C21—C26	1.380 (7)	C41—C42	1.370 (7)
C21—C22	1.386 (7)	C41—C46	1.375 (7)
C22—C23	1.359 (8)	C42—C43	1.375 (8)
C22—H22	0.9500	C42—H42	0.9500
C23—C24	1.410 (7)	C43—C44	1.388 (8)
C23—H23	0.9500	C43—H43	0.9500
C24—C25	1.381 (6)	C44—C45	1.384 (7)
C25—C26	1.376 (7)	C45—C46	1.403 (7)
C25—H25	0.9500	C45—H45	0.9500
C26—H26	0.9500	C46—H46	0.9500
C28—C29	1.524 (8)	C48—C49	1.555 (7)
C28—H28A	0.9900	C48—H48A	0.9900
C28—H28B	0.9900	C48—H48B	0.9900
C29—C30	1.531 (7)	C49—C50	1.515 (8)
C29—H29A	0.9900	C49—H49A	0.9900
C29—H29B	0.9900	C49—H49B	0.9900
C30—H30A	0.9800	C50—H50A	0.9800
C30—H30B	0.9800	C50—H50B	0.9800
C30—H30C	0.9800	C50—H50C	0.9800

O11—S11—O12	119.9 (2)	O31—S31—O32	121.1 (2)
O11—S11—N11	103.1 (2)	O31—S31—N31	103.6 (2)
O12—S11—N11	110.2 (2)	O32—S31—N31	108.8 (2)
O11—S11—C14	109.5 (2)	O31—S31—C34	108.8 (2)
O12—S11—C14	107.7 (2)	O32—S31—C34	107.8 (2)
N11—S11—C14	105.4 (2)	N31—S31—C34	105.9 (2)
C17—N11—S11	123.3 (3)	C37—N31—S31	122.8 (3)
C17—N11—H11N	118.3	C37—N31—H31N	118.6
S11—N11—H11N	118.3	S31—N31—H31N	118.6
C17—N12—C18	122.2 (4)	C37—N32—C38	122.7 (4)
C17—N12—H12N	118.9	C37—N32—H32N	118.6
C18—N12—H12N	118.9	C38—N32—H32N	118.6
C16—C11—C12	122.5 (5)	C36—C31—C32	120.7 (5)
C16—C11—Cl11	118.8 (4)	C36—C31—Cl31	119.3 (4)
C12—C11—Cl11	118.7 (4)	C32—C31—Cl31	120.0 (4)
C13—C12—C11	118.3 (5)	C33—C32—C31	119.7 (5)
C13—C12—H12	120.8	C33—C32—H32	120.2
C11—C12—H12	120.8	C31—C32—H32	120.2
C12—C13—C14	120.8 (5)	C32—C33—C34	120.1 (5)
C12—C13—H13	119.6	C32—C33—H33	119.9
C14—C13—H13	119.6	C34—C33—H33	119.9
C15—C14—C13	119.2 (5)	C33—C34—C35	119.6 (5)
C15—C14—S11	120.6 (4)	C33—C34—S31	120.3 (4)
C13—C14—S11	120.2 (4)	C35—C34—S31	120.1 (4)
C14—C15—C16	120.1 (5)	C36—C35—C34	119.5 (5)
C14—C15—H15	119.9	C36—C35—H35	120.3
C16—C15—H15	119.9	C34—C35—H35	120.3
C11—C16—C15	119.1 (5)	C35—C36—C31	120.5 (5)
C11—C16—H16	120.5	C35—C36—H36	119.8
C15—C16—H16	120.5	C31—C36—H36	119.8
O13—C17—N12	125.3 (5)	O33—C37—N32	125.7 (5)
O13—C17—N11	119.7 (5)	O33—C37—N31	119.3 (5)
N12—C17—N11	115.0 (4)	N32—C37—N31	115.0 (4)
N12—C18—C19	112.4 (4)	N32—C38—C39	112.5 (4)
N12—C18—H18A	109.1	N32—C38—H38A	109.1
C19—C18—H18A	109.1	C39—C38—H38A	109.1
N12—C18—H18B	109.1	N32—C38—H38B	109.1
C19—C18—H18B	109.1	C39—C38—H38B	109.1
H18A—C18—H18B	107.9	H38A—C38—H38B	107.8
C20—C19—C18	111.3 (5)	C38—C39—C40	111.3 (5)
C20—C19—H19A	109.4	C38—C39—H39A	109.4
C18—C19—H19A	109.4	C40—C39—H39A	109.4
C20—C19—H19B	109.4	C38—C39—H39B	109.4
C18—C19—H19B	109.4	C40—C39—H39B	109.4
H19A—C19—H19B	108.0	H39A—C39—H39B	108.0
C19—C20—H20A	109.5	C39—C40—H40A	109.5
C19—C20—H20B	109.5	C39—C40—H40B	109.5
H20A—C20—H20B	109.5	H40A—C40—H40B	109.5
C19—C20—H20C	109.5	C39—C40—H40C	109.5
H20A—C20—H20C	109.5	H40A—C40—H40C	109.5
H20B—C20—H20C	109.5	H40B—C40—H40C	109.5
O21—S21—O22	120.0 (2)	O41—S41—O42	120.6 (2)
O21—S21—N21	103.7 (2)	O41—S41—N41	102.8 (2)
O22—S21—N21	109.8 (2)	O42—S41—N41	109.9 (2)
O21—S21—C24	109.1 (2)	O41—S41—C44	108.9 (2)
O22—S21—C24	108.1 (2)	O42—S41—C44	107.8 (2)
N21—S21—C24	105.2 (2)	N41—S41—C44	106.0 (2)
C27—N21—S21	122.2 (3)	C47—N41—S41	122.8 (3)
C27—N21—H21N	118.9	C47—N41—H41N	118.6
S21—N21—H21N	118.9	S41—N41—H41N	118.6
C27—N22—C28	122.3 (4)	C47—N42—C48	123.5 (4)
C27—N22—H22N	118.9	C47—N42—H42N	118.3
C28—N22—H22N	118.9	C48—N42—H42N	118.3
C26—C21—C22	120.9 (5)	C42—C41—C46	121.9 (5)
C26—C21—Cl21	119.1 (4)	C42—C41—Cl41	120.4 (4)
C22—C21—Cl21	120.0 (4)	C46—C41—Cl41	117.6 (4)
C23—C22—C21	119.5 (5)	C41—C42—C43	119.3 (5)
C23—C22—H22	120.3	C41—C42—H42	120.4
C21—C22—H22	120.3	C43—C42—H42	120.4
C22—C23—C24	120.3 (5)	C42—C43—C44	120.2 (5)
C22—C23—H23	119.8	C42—C43—H43	119.9
C24—C23—H23	119.8	C44—C43—H43	119.9
C25—C24—C23	119.5 (5)	C45—C44—C43	120.5 (5)
C25—C24—S21	120.5 (4)	C45—C44—S41	119.9 (4)
C23—C24—S21	120.0 (4)	C43—C44—S41	119.6 (4)
C26—C25—C24	120.0 (5)	C44—C45—C46	119.0 (5)
C26—C25—H25	120.0	C44—C45—H45	120.5
C24—C25—H25	120.0	C46—C45—H45	120.5
C25—C26—C21	119.8 (5)	C41—C46—C45	119.0 (5)
C25—C26—H26	120.1	C41—C46—H46	120.5
C21—C26—H26	120.1	C45—C46—H46	120.5
O23—C27—N22	124.1 (5)	O43—C47—N42	125.2 (5)
O23—C27—N21	121.4 (5)	O43—C47—N41	120.1 (5)
N22—C27—N21	114.4 (4)	N42—C47—N41	114.6 (4)
N22—C28—C29	112.9 (4)	N42—C48—C49	113.0 (4)
N22—C28—H28A	109.0	N42—C48—H48A	109.0
C29—C28—H28A	109.0	C49—C48—H48A	109.0
N22—C28—H28B	109.0	N42—C48—H48B	109.0
C29—C28—H28B	109.0	C49—C48—H48B	109.0
H28A—C28—H28B	107.8	H48A—C48—H48B	107.8
C28—C29—C30	111.7 (5)	C50—C49—C48	112.6 (4)
C28—C29—H29A	109.3	C50—C49—H49A	109.1
C30—C29—H29A	109.3	C48—C49—H49A	109.1
C28—C29—H29B	109.3	C50—C49—H49B	109.1
C30—C29—H29B	109.3	C48—C49—H49B	109.1
H29A—C29—H29B	107.9	H49A—C49—H49B	107.8
C29—C30—H30A	109.5	C49—C50—H50A	109.5
C29—C30—H30B	109.5	C49—C50—H50B	109.5
H30A—C30—H30B	109.5	H50A—C50—H50B	109.5
C29—C30—H30C	109.5	C49—C50—H50C	109.5
H30A—C30—H30C	109.5	H50A—C50—H50C	109.5
H30B—C30—H30C	109.5	H50B—C50—H50C	109.5

O11—S11—N11—C17	176.1 (4)	O31—S31—N31—C37	−174.0 (4)
O12—S11—N11—C17	−54.7 (5)	O32—S31—N31—C37	56.0 (5)
C14—S11—N11—C17	61.3 (5)	C34—S31—N31—C37	−59.6 (4)
C16—C11—C12—C13	0.9 (9)	C36—C31—C32—C33	−0.5 (8)
Cl11—C11—C12—C13	−179.7 (4)	Cl31—C31—C32—C33	178.3 (4)
C11—C12—C13—C14	−0.8 (8)	C31—C32—C33—C34	0.1 (9)
C12—C13—C14—C15	−0.1 (8)	C32—C33—C34—C35	0.7 (8)
C12—C13—C14—S11	179.5 (4)	C32—C33—C34—S31	−178.8 (4)
O11—S11—C14—C15	143.6 (4)	O31—S31—C34—C33	36.7 (5)
O12—S11—C14—C15	11.6 (5)	O32—S31—C34—C33	169.6 (4)
N11—S11—C14—C15	−106.1 (4)	N31—S31—C34—C33	−74.1 (5)
O11—S11—C14—C13	−36.0 (5)	O31—S31—C34—C35	−142.8 (4)
O12—S11—C14—C13	−168.0 (4)	O32—S31—C34—C35	−9.9 (5)
N11—S11—C14—C13	74.3 (5)	N31—S31—C34—C35	106.4 (4)
C13—C14—C15—C16	0.9 (8)	C33—C34—C35—C36	−1.2 (8)
S11—C14—C15—C16	−178.7 (4)	S31—C34—C35—C36	178.3 (4)
C12—C11—C16—C15	−0.2 (9)	C34—C35—C36—C31	0.8 (8)
Cl11—C11—C16—C15	−179.6 (4)	C32—C31—C36—C35	0.0 (8)
C14—C15—C16—C11	−0.7 (8)	Cl31—C31—C36—C35	−178.8 (4)
C18—N12—C17—O13	1.6 (8)	C38—N32—C37—O33	−3.5 (9)
C18—N12—C17—N11	179.2 (4)	C38—N32—C37—N31	177.5 (5)
S11—N11—C17—O13	5.9 (7)	S31—N31—C37—O33	−19.2 (7)
S11—N11—C17—N12	−171.8 (4)	S31—N31—C37—N32	159.9 (4)
C17—N12—C18—C19	−84.2 (6)	C37—N32—C38—C39	84.7 (6)
N12—C18—C19—C20	179.7 (4)	N32—C38—C39—C40	−177.7 (4)
O21—S21—N21—C27	−174.2 (4)	O41—S41—N41—C47	179.0 (4)
O22—S21—N21—C27	56.4 (5)	O42—S41—N41—C47	−51.5 (5)
C24—S21—N21—C27	−59.7 (4)	C44—S41—N41—C47	64.8 (5)
C26—C21—C22—C23	0.1 (8)	C46—C41—C42—C43	1.0 (8)
Cl21—C21—C22—C23	178.8 (4)	Cl41—C41—C42—C43	−178.2 (4)
C21—C22—C23—C24	−0.7 (9)	C41—C42—C43—C44	0.3 (8)
C22—C23—C24—C25	0.3 (8)	C42—C43—C44—C45	−1.9 (8)
C22—C23—C24—S21	−177.3 (4)	C42—C43—C44—S41	178.5 (4)
O21—S21—C24—C25	−137.3 (4)	O41—S41—C44—C45	147.3 (4)
O22—S21—C24—C25	−5.3 (5)	O42—S41—C44—C45	14.9 (5)
N21—S21—C24—C25	112.0 (5)	N41—S41—C44—C45	−102.7 (4)
O21—S21—C24—C23	40.2 (5)	O41—S41—C44—C43	−33.2 (5)
O22—S21—C24—C23	172.2 (4)	O42—S41—C44—C43	−165.6 (4)
N21—S21—C24—C23	−70.5 (5)	N41—S41—C44—C43	76.8 (4)
C23—C24—C25—C26	0.8 (8)	C43—C44—C45—C46	2.1 (8)
S21—C24—C25—C26	178.3 (4)	S41—C44—C45—C46	−178.3 (4)
C24—C25—C26—C21	−1.4 (9)	C42—C41—C46—C45	−0.8 (9)
C22—C21—C26—C25	0.9 (8)	Cl41—C41—C46—C45	178.5 (4)
Cl21—C21—C26—C25	−177.7 (4)	C44—C45—C46—C41	−0.8 (8)
C28—N22—C27—O23	−4.5 (8)	C48—N42—C47—O43	5.3 (8)
C28—N22—C27—N21	176.4 (5)	C48—N42—C47—N41	−177.9 (5)
S21—N21—C27—O23	−18.1 (7)	S41—N41—C47—O43	0.7 (7)
S21—N21—C27—N22	161.1 (4)	S41—N41—C47—N42	−176.3 (4)
C27—N22—C28—C29	86.6 (6)	C47—N42—C48—C49	−107.6 (5)
N22—C28—C29—C30	−179.0 (4)	N42—C48—C49—C50	66.3 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11N···O23ⁱ	0.88	1.90	2.744 (5)	160
N12—H12N···O22ⁱ	0.88	2.28	3.008 (5)	140
N12—H12N···O23ⁱ	0.88	2.57	3.295 (5)	140
N21—H21N···O13	0.88	2.04	2.750 (5)	137
N22—H22N···O12	0.88	2.31	3.027 (5)	138
N22—H22N···O13	0.88	2.45	3.183 (5)	141
N31—H31N···O43	0.88	2.06	2.725 (5)	132
N32—H32N···O42	0.88	2.28	3.005 (5)	140
N32—H32N···O43	0.88	2.53	3.237 (5)	138
N41—H41N···O33ⁱ	0.88	1.86	2.726 (5)	170
N42—H42N···O32ⁱ	0.88	2.22	2.994 (5)	146
N42—H42N···O33ⁱ	0.88	2.68	3.386 (5)	139

Symmetry code: (i) x, y+1, z.

Experimental details

	(bIICPA200K)	(bIIICPA100K)
Crystal data
Chemical formula	C₁₀H₁₃ClN₂O₃S	C₁₀H₁₃ClN₂O₃S
M_r	276.73	276.73
Crystal system, space group	Monoclinic, P2/c	Monoclinic, P2/n
Temperature (K)	200	100
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)
V (Å³)	2582.71 (13)	5026.6 (3)
Z	8	16
Radiation type	Mo Kα	Mo Kα
µ (mm⁻¹)	0.46	0.47
Crystal size (mm)	0.32 × 0.20 × 0.08	0.22 × 0.15 × 0.06

Data collection
Diffractometer	Oxford Diffraction KM4 CCD diffractometer	Oxford Diffraction KM4 CCD diffractometer
Absorption correction	Multi-scan CrysAlis RED (Oxford Diffraction, 2008)	Multi-scan CrysAlis RED (Oxford Diffraction, 2008)
T_min, T_max	0.899, 0.965	0.946, 0.973
No. of measured, independent and observed [I > 2σ(I)] reflections	53248, 7720, 2794	42040, 14436, 6814
R_int	0.111	0.087
(sin θ/λ)_max (Å⁻¹)	0.602	0.610

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.147, 0.75	0.053, 0.139, 0.81
No. of reflections	7720	14436
No. of parameters	310	618
H-atom treatment	H-atom parameters constrained	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.30	0.37, −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···A	D—H	H···A	D···A	D—H···A
N11—H11N···O23ⁱ	0.88	2.00	2.737 (4)	140.8
N12—H12N···O22ⁱ	0.88	2.37	3.100 (5)	140.7
N12—H12N···O23ⁱ	0.88	2.55	3.271 (5)	139.5
N21—H21N···O13	0.88	1.89	2.728 (4)	158.9
N22—H22N···O12	0.88	2.36	3.086 (5)	140.0
N22—H22N···O13	0.88	2.52	3.244 (5)	139.8

Symmetry code: (i) x, y+1, z.

Hydrogen-bond geometry (Å, º) for (bIIICPA100K) top

D—H···A	D—H	H···A	D···A	D—H···A
N11—H11N···O23ⁱ	0.88	1.90	2.744 (5)	159.5
N12—H12N···O22ⁱ	0.88	2.28	3.008 (5)	139.8
N12—H12N···O23ⁱ	0.88	2.57	3.295 (5)	139.7
N21—H21N···O13	0.88	2.04	2.750 (5)	137.2
N22—H22N···O12	0.88	2.31	3.027 (5)	138.4
N22—H22N···O13	0.88	2.45	3.183 (5)	140.7
N31—H31N···O43	0.88	2.06	2.725 (5)	132.0
N32—H32N···O42	0.88	2.28	3.005 (5)	140.1
N32—H32N···O43	0.88	2.53	3.237 (5)	138.0
N41—H41N···O33ⁱ	0.88	1.86	2.726 (5)	169.6
N42—H42N···O32ⁱ	0.88	2.22	2.994 (5)	146.0
N42—H42N···O33ⁱ	0.88	2.68	3.386 (5)	138.5

Symmetry code: (i) x, y+1, z.

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