A conformational polymorphic transition in the high-temperature [epsilon]-form of chlorpropamide on cooling: a new [epsilon]′-form

Structural changes in the high-temperature [epsilon]-polymorph of chlorpropamide, 4-chloro-N-(propylaminocarbonyl)benzenesulfonamide, C₁₀H₁₃ClN₂O₃S, on cooling down to 100 K and on reverse heating were followed by single-crystal X-ray diffraction. At temperatures below 200 K the phase transition into a new polymorph (termed the [epsilon]′-form) has been observed for the first time. The polymorphic transition preserves the space group Pna2₁, is reversible and is accompanied by discontinuous changes in the cell volume and parameters, resulting from changes in molecular conformation. As shown by IR spectroscopy and X-ray powder diffraction, the phase transition in a powder sample is inhomogeneous throughout the bulk, and the two phases co-exist in a wide temperature range. The cell parameters and the molecular conformation in the new polymorph are close to those in the previously known α-polymorph, but the packing of the z-shaped molecular ribbons linked by hydrogen bonds inherits that of the [epsilon]-form and is different from the packing in the α-polymorph. A structural study of the α-polymorph in the same temperature range has revealed no phase transitions.

Computing details

Data collection: CrysAlis CCD (Oxford Diffraction,2008) for enewcpa100; CrysAlis CCD (Oxford Diffraction, 2008) for ecpa250, enewcpa200; STADI4 (STOE & Cie, 1997) for acpa105, acpa200, acpa295. Cell refinement: CrysAlis RED (Oxford Diffraction,2008) for enewcpa100; CrysAlis RED (Oxford Diffraction, 2008) for ecpa250, enewcpa200; STADI4 (STOE & Cie, 1997) for acpa105, acpa200, acpa295. Data reduction: CrysAlis RED (Oxford Diffraction,2008) for enewcpa100; CrysAlis RED for ecpa250, enewcpa200; X-RED (STOE & Cie, 1997) for acpa105, acpa200, acpa295. For all compounds, program(s) used to solve structure: SHELXS97 (Sheldrick, 2008). Program(s) used to refine structure: SHELXS97 (Sheldrick, 2008) for enewcpa100; SHELXL97 (Sheldrick, 2008) for ecpa250, enewcpa200, acpa105, acpa200, acpa295.

(enewcpa100) 4-chloro-N-((propylaminocarbonyl)benzenesulfonamide

Crystal data

C10H13ClN2O3S	Dx = 1.489 Mg m^−3
Mr = 276.73	Melting point: Kinetic phase transition K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 1973 reflections
a = 26.4353 (19) Å	θ = 3.1–29.1°
b = 5.1398 (4) Å	µ = 0.48 mm^−1
c = 9.0845 (6) Å	T = 100 K
V = 1234.33 (15) Å^3	Plate, colourless
Z = 4	0.40 × 0.15 × 0.03 mm
F(000) = 576

Data collection

Oxford Diffraction KM4 CCD diffractometer	1995 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1399 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.057
Detector resolution: 10.3457 pixels mm^-1	θmax = 25.0°, θmin = 3.1°
ω scans	h = −31→31
Absorption correction: multi-scan CrysAlis RED (Oxford Diffraction, 2008)	k = −6→4
Tmin = 0.800, Tmax = 0.986	l = −9→10
4372 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.047	H-atom parameters constrained
wR(F^2) = 0.088	w = 1/[σ^2(Fo^2) + (0.0357P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.97	(Δ/σ)max < 0.001
1995 reflections	Δρmax = 0.43 e Å^−3
155 parameters	Δρmin = −0.31 e Å^−3
1 restraint	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.17 (11)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.29277 (14)	1.2677 (9)	0.2638 (6)	0.0203 (11)
C2	0.29740 (17)	1.1116 (11)	0.1437 (5)	0.0264 (13)
H2	0.2736	1.1228	0.0656	0.032*
C3	0.33702 (16)	0.9363 (11)	0.1359 (5)	0.0253 (13)
H3	0.3405	0.8244	0.0533	0.030*
C4	0.37172 (13)	0.9263 (8)	0.2512 (6)	0.0173 (10)
C5	0.36672 (16)	1.0843 (10)	0.3723 (5)	0.0215 (12)
H5	0.3904	1.0734	0.4507	0.026*
C6	0.32703 (16)	1.2591 (11)	0.3797 (5)	0.0257 (12)
H6	0.3233	1.3709	0.4622	0.031*
C7	0.49785 (14)	1.0630 (8)	0.2535 (6)	0.0164 (10)
C8	0.55976 (14)	1.4167 (9)	0.2298 (5)	0.0223 (11)
H8A	0.5463	1.4680	0.3273	0.027*
H8B	0.5580	1.5708	0.1647	0.027*
C9	0.61446 (14)	1.3368 (9)	0.2468 (6)	0.0222 (10)
H9A	0.6169	1.1940	0.3195	0.027*
H9B	0.6273	1.2708	0.1514	0.027*
C10	0.64680 (15)	1.5611 (9)	0.2965 (5)	0.0234 (12)
H10A	0.6344	1.6254	0.3915	0.035*
H10B	0.6451	1.7012	0.2235	0.035*
H10C	0.6819	1.5029	0.3070	0.035*
O1	0.41212 (11)	0.5239 (7)	0.1230 (3)	0.0240 (8)
O2	0.43469 (11)	0.6199 (6)	0.3833 (3)	0.0225 (8)
O3	0.49476 (11)	1.0760 (6)	0.3889 (3)	0.0233 (8)
S1	0.42316 (4)	0.7072 (2)	0.23721 (13)	0.0205 (3)
Cl1	0.24323 (4)	1.4913 (3)	0.27008 (13)	0.0312 (3)
N1	0.46979 (12)	0.8809 (8)	0.1728 (4)	0.0191 (10)
H1N	0.4780	0.8584	0.0798	0.023*
N2	0.52773 (13)	1.2108 (8)	0.1687 (4)	0.0199 (10)
H2N	0.5281	1.1832	0.0731	0.024*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.014 (2)	0.018 (3)	0.028 (3)	−0.0003 (19)	0.006 (2)	0.002 (3)
C2	0.028 (3)	0.033 (4)	0.019 (3)	0.005 (3)	−0.002 (2)	−0.003 (3)
C3	0.023 (3)	0.030 (4)	0.022 (3)	0.001 (3)	0.004 (2)	−0.004 (3)
C4	0.014 (2)	0.019 (3)	0.019 (2)	−0.0041 (18)	0.006 (2)	−0.005 (3)
C5	0.023 (2)	0.025 (3)	0.017 (2)	0.001 (2)	−0.002 (2)	0.003 (3)
C6	0.026 (3)	0.030 (3)	0.021 (2)	−0.005 (3)	0.007 (2)	−0.009 (3)
C7	0.0120 (19)	0.009 (3)	0.028 (3)	−0.0011 (17)	0.002 (2)	0.000 (3)
C8	0.025 (2)	0.020 (3)	0.022 (3)	−0.006 (2)	−0.001 (2)	0.000 (3)
C9	0.024 (2)	0.020 (3)	0.023 (2)	−0.0016 (19)	0.000 (3)	−0.010 (3)
C10	0.026 (2)	0.021 (3)	0.023 (3)	−0.001 (2)	0.001 (2)	0.000 (2)
O1	0.0285 (17)	0.021 (2)	0.0226 (18)	−0.0006 (16)	0.0021 (14)	−0.0065 (18)
O2	0.0292 (17)	0.022 (2)	0.0159 (16)	−0.0019 (15)	−0.0031 (15)	0.0001 (15)
O3	0.0301 (18)	0.027 (2)	0.0123 (17)	−0.0017 (16)	−0.0028 (15)	−0.0007 (17)
S1	0.0212 (5)	0.0192 (7)	0.0212 (6)	−0.0026 (5)	−0.0016 (6)	0.0005 (7)
Cl1	0.0263 (6)	0.0353 (7)	0.0321 (6)	0.0091 (6)	0.0025 (6)	−0.0007 (7)
N1	0.023 (2)	0.022 (2)	0.0129 (19)	−0.001 (2)	0.0080 (17)	−0.0031 (17)
N2	0.022 (2)	0.024 (3)	0.0139 (19)	−0.003 (2)	0.0013 (17)	−0.002 (2)

Geometric parameters (Å, º)

C1—C2	1.360 (7)	C8—N2	1.464 (6)
C1—C6	1.390 (6)	C8—C9	1.511 (5)
C1—Cl1	1.743 (4)	C8—H8A	0.9900
C2—C3	1.383 (6)	C8—H8B	0.9900
C2—H2	0.9500	C9—C10	1.505 (6)
C3—C4	1.393 (6)	C9—H9A	0.9900
C3—H3	0.9500	C9—H9B	0.9900
C4—C5	1.374 (7)	C10—H10A	0.9800
C4—S1	1.770 (4)	C10—H10B	0.9800
C5—C6	1.383 (6)	C10—H10C	0.9800
C5—H5	0.9500	O1—S1	1.432 (3)
C6—H6	0.9500	O2—S1	1.434 (3)
C7—O3	1.234 (6)	S1—N1	1.630 (4)
C7—N2	1.339 (5)	N1—H1N	0.8800
C7—N1	1.402 (6)	N2—H2N	0.8800
C2—C1—C6	122.1 (4)	H8A—C8—H8B	107.7
C2—C1—Cl1	118.9 (4)	C10—C9—C8	111.5 (4)
C6—C1—Cl1	119.0 (4)	C10—C9—H9A	109.3
C1—C2—C3	119.5 (5)	C8—C9—H9A	109.3
C1—C2—H2	120.2	C10—C9—H9B	109.3
C3—C2—H2	120.2	C8—C9—H9B	109.3
C2—C3—C4	119.0 (5)	H9A—C9—H9B	108.0
C2—C3—H3	120.5	C9—C10—H10A	109.5
C4—C3—H3	120.5	C9—C10—H10B	109.5
C5—C4—C3	121.1 (4)	H10A—C10—H10B	109.5
C5—C4—S1	120.5 (4)	C9—C10—H10C	109.5
C3—C4—S1	118.4 (4)	H10A—C10—H10C	109.5
C4—C5—C6	119.7 (4)	H10B—C10—H10C	109.5
C4—C5—H5	120.1	O1—S1—O2	120.5 (2)
C6—C5—H5	120.1	O1—S1—N1	104.72 (19)
C5—C6—C1	118.6 (4)	O2—S1—N1	110.06 (19)
C5—C6—H6	120.7	O1—S1—C4	108.3 (2)
C1—C6—H6	120.7	O2—S1—C4	107.2 (2)
O3—C7—N2	125.5 (4)	N1—S1—C4	105.0 (2)
O3—C7—N1	121.5 (4)	C7—N1—S1	125.3 (3)
N2—C7—N1	113.0 (4)	C7—N1—H1N	117.3
N2—C8—C9	113.3 (4)	S1—N1—H1N	117.3
N2—C8—H8A	108.9	C7—N2—C8	122.2 (4)
C9—C8—H8A	108.9	C7—N2—H2N	118.9
N2—C8—H8B	108.9	C8—N2—H2N	118.9
C9—C8—H8B	108.9
C6—C1—C2—C3	0.6 (7)	C5—C4—S1—O2	33.5 (4)
Cl1—C1—C2—C3	178.9 (4)	C3—C4—S1—O2	−147.2 (4)
C1—C2—C3—C4	−0.8 (7)	C5—C4—S1—N1	−83.5 (4)
C2—C3—C4—C5	1.0 (7)	C3—C4—S1—N1	95.8 (4)
C2—C3—C4—S1	−178.3 (4)	O3—C7—N1—S1	12.3 (6)
C3—C4—C5—C6	−0.9 (7)	N2—C7—N1—S1	−168.8 (3)
S1—C4—C5—C6	178.3 (4)	O1—S1—N1—C7	−171.1 (3)
C4—C5—C6—C1	0.7 (7)	O2—S1—N1—C7	−40.2 (4)
C2—C1—C6—C5	−0.5 (7)	C4—S1—N1—C7	74.9 (4)
Cl1—C1—C6—C5	−178.8 (4)	O3—C7—N2—C8	−2.2 (7)
N2—C8—C9—C10	174.8 (4)	N1—C7—N2—C8	179.0 (3)
C5—C4—S1—O1	165.0 (4)	C9—C8—N2—C7	100.4 (5)
C3—C4—S1—O1	−15.7 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3^i	0.88	1.91	2.753 (5)	161
N2—H2N···O2^i	0.88	2.23	2.910 (5)	134
N2—H2N···O3^i	0.88	2.22	2.998 (5)	147
C10—H10A···O1^ii	0.98	2.55	3.378 (5)	142
C2—H2···Cl1^iii	0.95	2.80	3.613 (5)	144

Symmetry codes: (i) −x+1, −y+2, z−1/2; (ii) −x+1, −y+2, z+1/2; (iii) −x+1/2, y−1/2, z−1/2.

(ecpa250) 4-chloro-N-((propylaminocarbonyl)benzenesulfonamide

Crystal data

C10H13ClN2O3S	Dx = 1.383 Mg m^−3
Mr = 276.73	Melting point: 401 K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 1587 reflections
a = 19.805 (2) Å	θ = 2.8–29.2°
b = 7.3500 (7) Å	µ = 0.44 mm^−1
c = 9.1295 (9) Å	T = 250 K
V = 1329.0 (2) Å^3	Plate, colourless
Z = 4	0.40 × 0.15 × 0.03 mm
F(000) = 576

Data collection

Oxford Diffraction KM4 CCD diffractometer	1247 independent reflections
Radiation source: Enhance (Mo) X-ray Source	714 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.075
Detector resolution: 10.3457 pixels mm^-1	θmax = 25.0°, θmin = 3.0°
ω scans	h = −22→23
Absorption correction: multi-scan CrysAlis RED (Oxford Diffraction, 2008)	k = −8→8
Tmin = 0.765, Tmax = 0.987	l = −10→10
5838 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.044	H-atom parameters constrained
wR(F^2) = 0.098	w = 1/[σ^2(Fo^2) + (0.0433P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.85	(Δ/σ)max < 0.001
1247 reflections	Δρmax = 0.30 e Å^−3
155 parameters	Δρmin = −0.26 e Å^−3
1 restraint	Absolute structure: Merged equivalents
Primary atom site location: structure-invariant direct methods

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.2807 (3)	0.3441 (10)	0.4088 (9)	0.059 (2)
C2	0.3166 (4)	0.3278 (9)	0.2762 (7)	0.060 (2)
H2	0.3166	0.4222	0.2067	0.072*
C3	0.3515 (4)	0.1705 (10)	0.2522 (8)	0.061 (2)
H3	0.3762	0.1574	0.1649	0.073*
C4	0.3515 (3)	0.0315 (8)	0.3517 (7)	0.0466 (18)
C5	0.3170 (3)	0.0495 (10)	0.4828 (8)	0.0571 (19)
H5	0.3180	−0.0439	0.5531	0.068*
C6	0.2807 (3)	0.2088 (11)	0.5086 (8)	0.065 (2)
H6	0.2561	0.2221	0.5960	0.078*
C7	0.5095 (3)	0.0281 (8)	0.3278 (8)	0.0429 (15)
C8	0.5944 (3)	0.2665 (8)	0.3079 (8)	0.0522 (16)
H8A	0.6354	0.2729	0.2478	0.063*
H8B	0.6080	0.2325	0.4075	0.063*
C9	0.5622 (4)	0.4507 (9)	0.3121 (11)	0.085 (3)
H9A	0.5213	0.4453	0.3723	0.102*
H9B	0.5489	0.4859	0.2127	0.102*
C10	0.6092 (5)	0.5923 (12)	0.3738 (12)	0.122 (4)
H10A	0.6153	0.5715	0.4779	0.183*
H10B	0.5901	0.7124	0.3584	0.183*
H10C	0.6526	0.5844	0.3247	0.183*
N1	0.4689 (2)	−0.0985 (7)	0.2532 (5)	0.0439 (13)
H1N	0.4828	−0.1405	0.1694	0.053*
N2	0.5501 (2)	0.1244 (7)	0.2489 (5)	0.0457 (13)
H2N	0.5513	0.1037	0.1551	0.055*
O1	0.3670 (2)	−0.2626 (6)	0.1953 (4)	0.0547 (12)
O2	0.4064 (2)	−0.2659 (6)	0.4539 (4)	0.0505 (11)
O3	0.5039 (2)	0.0383 (6)	0.4655 (4)	0.0560 (12)
S1	0.39703 (8)	−0.1694 (2)	0.31753 (16)	0.0440 (4)
Cl1	0.23578 (9)	0.5438 (3)	0.4358 (3)	0.0929 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.056 (4)	0.058 (5)	0.061 (6)	−0.009 (3)	0.010 (4)	0.005 (5)
C2	0.090 (5)	0.041 (5)	0.047 (6)	0.000 (4)	−0.002 (4)	0.016 (4)
C3	0.088 (5)	0.054 (5)	0.040 (4)	−0.003 (4)	0.015 (4)	0.003 (4)
C4	0.054 (4)	0.041 (4)	0.045 (5)	−0.011 (3)	−0.001 (3)	0.002 (3)
C5	0.061 (4)	0.063 (5)	0.047 (5)	0.007 (4)	0.021 (4)	0.013 (4)
C6	0.056 (4)	0.083 (6)	0.056 (5)	0.006 (4)	0.019 (3)	−0.004 (5)
C7	0.043 (3)	0.046 (4)	0.040 (4)	−0.001 (3)	−0.003 (4)	0.004 (4)
C8	0.068 (4)	0.058 (4)	0.031 (3)	−0.014 (3)	−0.007 (4)	−0.003 (5)
C9	0.108 (6)	0.060 (5)	0.088 (6)	−0.002 (4)	−0.049 (6)	−0.016 (6)
C10	0.159 (8)	0.069 (6)	0.138 (11)	−0.012 (6)	−0.073 (8)	−0.017 (6)
N1	0.047 (3)	0.057 (3)	0.027 (3)	−0.001 (3)	0.005 (2)	−0.008 (3)
N2	0.059 (3)	0.056 (4)	0.022 (3)	−0.010 (3)	0.005 (2)	−0.002 (3)
O1	0.071 (3)	0.057 (3)	0.035 (3)	−0.016 (2)	−0.007 (2)	−0.008 (2)
O2	0.072 (3)	0.054 (3)	0.025 (2)	−0.005 (2)	−0.002 (2)	0.011 (2)
O3	0.076 (3)	0.079 (3)	0.013 (2)	−0.021 (3)	−0.002 (2)	−0.003 (2)
S1	0.0580 (8)	0.0494 (9)	0.0246 (7)	−0.0059 (8)	−0.0011 (9)	0.0011 (10)
Cl1	0.0843 (13)	0.0636 (12)	0.131 (2)	0.0080 (10)	0.0331 (15)	−0.0050 (15)

Geometric parameters (Å, º)

C1—C6	1.349 (9)	C8—N2	1.467 (7)
C1—C2	1.409 (10)	C8—C9	1.497 (9)
C1—Cl1	1.734 (7)	C8—H8A	0.9800
C2—C3	1.365 (9)	C8—H8B	0.9800
C2—H2	0.9400	C9—C10	1.506 (10)
C3—C4	1.367 (9)	C9—H9A	0.9800
C3—H3	0.9400	C9—H9B	0.9800
C4—C5	1.385 (9)	C10—H10A	0.9700
C4—S1	1.758 (6)	C10—H10B	0.9700
C5—C6	1.394 (9)	C10—H10C	0.9700
C5—H5	0.9400	N1—S1	1.626 (5)
C6—H6	0.9400	N1—H1N	0.8700
C7—O3	1.264 (8)	N2—H2N	0.8700
C7—N2	1.291 (7)	O1—S1	1.439 (4)
C7—N1	1.406 (7)	O2—S1	1.445 (4)
C6—C1—C2	121.2 (6)	H8A—C8—H8B	107.7
C6—C1—Cl1	121.9 (6)	C8—C9—C10	111.8 (7)
C2—C1—Cl1	117.0 (6)	C8—C9—H9A	109.3
C3—C2—C1	117.8 (6)	C10—C9—H9A	109.3
C3—C2—H2	121.1	C8—C9—H9B	109.3
C1—C2—H2	121.1	C10—C9—H9B	109.3
C2—C3—C4	121.7 (6)	H9A—C9—H9B	107.9
C2—C3—H3	119.1	C9—C10—H10A	109.5
C4—C3—H3	119.1	C9—C10—H10B	109.5
C3—C4—C5	120.2 (6)	H10A—C10—H10B	109.5
C3—C4—S1	120.6 (5)	C9—C10—H10C	109.5
C5—C4—S1	119.1 (5)	H10A—C10—H10C	109.5
C4—C5—C6	118.7 (6)	H10B—C10—H10C	109.5
C4—C5—H5	120.6	C7—N1—S1	122.5 (4)
C6—C5—H5	120.6	C7—N1—H1N	118.7
C1—C6—C5	120.4 (7)	S1—N1—H1N	118.7
C1—C6—H6	119.8	C7—N2—C8	123.9 (5)
C5—C6—H6	119.8	C7—N2—H2N	118.0
O3—C7—N2	125.3 (6)	C8—N2—H2N	118.0
O3—C7—N1	118.1 (5)	O1—S1—O2	119.2 (2)
N2—C7—N1	116.6 (6)	O1—S1—N1	103.6 (3)
N2—C8—C9	113.5 (6)	O2—S1—N1	110.9 (3)
N2—C8—H8A	108.9	O1—S1—C4	109.0 (3)
C9—C8—H8A	108.9	O2—S1—C4	109.0 (3)
N2—C8—H8B	108.9	N1—S1—C4	104.1 (3)
C9—C8—H8B	108.9
C6—C1—C2—C3	0.0 (10)	O3—C7—N2—C8	−2.5 (9)
Cl1—C1—C2—C3	−179.2 (5)	N1—C7—N2—C8	178.0 (5)
C1—C2—C3—C4	0.7 (10)	C9—C8—N2—C7	−89.5 (8)
C2—C3—C4—C5	−1.8 (10)	C7—N1—S1—O1	168.0 (4)
C2—C3—C4—S1	−180.0 (6)	C7—N1—S1—O2	−63.0 (5)
C3—C4—C5—C6	2.1 (9)	C7—N1—S1—C4	54.0 (5)
S1—C4—C5—C6	−179.6 (5)	C3—C4—S1—O1	−66.4 (6)
C2—C1—C6—C5	0.4 (11)	C5—C4—S1—O1	115.3 (5)
Cl1—C1—C6—C5	179.6 (5)	C3—C4—S1—O2	162.0 (5)
C4—C5—C6—C1	−1.5 (10)	C5—C4—S1—O2	−16.2 (6)
N2—C8—C9—C10	179.8 (7)	C3—C4—S1—N1	43.6 (6)
O3—C7—N1—S1	25.7 (7)	C5—C4—S1—N1	−134.6 (5)
N2—C7—N1—S1	−154.8 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3^i	0.87	2.02	2.718 (6)	136
N2—H2N···O2^i	0.87	2.35	3.013 (6)	134
N2—H2N···O3^i	0.87	2.30	3.044 (6)	144
C2—H2···O1^ii	0.94	2.52	3.256 (8)	135

Symmetry codes: (i) −x+1, −y, z−1/2; (ii) x, y+1, z.

(enewcpa200) 4-chloro-N-((propylaminocarbonyl)benzenesulfonamide

Crystal data

C10H13ClN2O3S	Dx = 1.467 Mg m^−3
Mr = 276.73	Melting point: Kinetic phase transition K
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 1165 reflections
a = 26.455 (4) Å	θ = 3.1–29.1°
b = 5.1924 (9) Å	µ = 0.47 mm^−1
c = 9.1219 (11) Å	T = 200 K
V = 1253.0 (3) Å^3	Plate, colourless
Z = 4	0.40 × 0.15 × 0.03 mm
F(000) = 576

Data collection

Oxford Diffraction KM4 CCD diffractometer	1181 independent reflections
Radiation source: Enhance (Mo) X-ray Source	630 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.110
Detector resolution: 10.3457 pixels mm^-1	θmax = 25.0°, θmin = 3.1°
ω scans	h = −24→31
Absorption correction: multi-scan CrysAlis RED (Oxford Diffraction, 2008)	k = −6→6
Tmin = 0.808, Tmax = 0.986	l = −10→10
4998 measured reflections

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.054	H-atom parameters constrained
wR(F^2) = 0.127	w = 1/[σ^2(Fo^2) + (0.0641P)^2] where P = (Fo^2 + 2Fc^2)/3
S = 0.90	(Δ/σ)max < 0.001
1181 reflections	Δρmax = 0.44 e Å^−3
155 parameters	Δρmin = −0.25 e Å^−3
1 restraint	Absolute structure: Merged equivalents
Primary atom site location: structure-invariant direct methods

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.2937 (3)	1.2672 (18)	0.2626 (10)	0.046 (2)
C2	0.2978 (4)	1.111 (2)	0.1444 (10)	0.052 (3)
H2	0.2733	1.1162	0.0684	0.063*
C3	0.3372 (3)	0.948 (2)	0.1366 (9)	0.045 (3)
H3	0.3416	0.8465	0.0509	0.055*
C4	0.3718 (3)	0.9248 (15)	0.2509 (11)	0.037 (2)
C5	0.3670 (3)	1.0872 (17)	0.3724 (10)	0.041 (2)
H5	0.3914	1.0846	0.4487	0.049*
C6	0.3272 (3)	1.2468 (19)	0.3789 (9)	0.049 (3)
H6	0.3218	1.3474	0.4645	0.058*
C7	0.4984 (3)	1.0641 (14)	0.2539 (12)	0.035 (2)
C8	0.5601 (3)	1.4116 (16)	0.2305 (11)	0.041 (2)
H8A	0.5468	1.4587	0.3283	0.049*
H8B	0.5574	1.5658	0.1672	0.049*
C9	0.6141 (3)	1.3446 (15)	0.2459 (12)	0.041 (2)
H9A	0.6268	1.2830	0.1501	0.049*
H9B	0.6172	1.2008	0.3166	0.049*
C10	0.6464 (3)	1.5612 (18)	0.2963 (12)	0.056 (3)
H10A	0.6350	1.6196	0.3929	0.085*
H10B	0.6441	1.7037	0.2262	0.085*
H10C	0.6816	1.5031	0.3030	0.085*
O1	0.4128 (2)	0.5334 (12)	0.1233 (6)	0.0484 (18)
O2	0.4348 (2)	0.6261 (12)	0.3815 (6)	0.0472 (17)
O3	0.4948 (2)	1.0803 (11)	0.3883 (6)	0.0437 (16)
S1	0.42358 (8)	0.7142 (4)	0.2372 (2)	0.0385 (6)
Cl1	0.24388 (9)	1.4871 (5)	0.2703 (3)	0.0635 (8)
N1	0.4700 (2)	0.8843 (15)	0.1740 (8)	0.0410 (19)
H1N	0.4782	0.8619	0.0814	0.049*
N2	0.5282 (3)	1.2106 (14)	0.1695 (8)	0.041 (2)
H2N	0.5285	1.1843	0.0742	0.049*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.030 (5)	0.071 (7)	0.036 (6)	0.000 (5)	0.012 (5)	−0.001 (7)
C2	0.045 (6)	0.076 (8)	0.036 (6)	0.006 (6)	0.000 (5)	−0.005 (6)
C3	0.039 (6)	0.071 (8)	0.026 (5)	−0.001 (6)	−0.001 (4)	−0.003 (5)
C4	0.023 (4)	0.049 (6)	0.039 (5)	−0.012 (4)	0.007 (5)	0.011 (6)
C5	0.045 (6)	0.040 (6)	0.037 (5)	0.004 (5)	−0.002 (5)	0.001 (5)
C6	0.050 (6)	0.069 (7)	0.027 (5)	0.002 (6)	0.009 (5)	−0.017 (6)
C7	0.022 (4)	0.027 (5)	0.056 (6)	0.004 (4)	−0.005 (5)	−0.002 (6)
C8	0.042 (5)	0.038 (5)	0.044 (6)	−0.009 (4)	0.003 (5)	0.001 (6)
C9	0.038 (5)	0.041 (5)	0.042 (5)	−0.001 (4)	−0.004 (5)	0.001 (6)
C10	0.049 (5)	0.063 (7)	0.056 (6)	−0.014 (5)	0.005 (5)	−0.014 (6)
O1	0.061 (4)	0.036 (4)	0.048 (4)	−0.001 (3)	0.001 (3)	−0.009 (4)
O2	0.065 (4)	0.042 (4)	0.035 (3)	−0.008 (3)	−0.005 (3)	0.000 (3)
O3	0.058 (4)	0.053 (4)	0.021 (3)	−0.008 (3)	−0.001 (3)	−0.006 (3)
S1	0.0420 (12)	0.0378 (13)	0.0357 (12)	−0.0038 (11)	−0.0033 (14)	−0.0033 (15)
Cl1	0.0522 (14)	0.0721 (16)	0.0662 (17)	0.0173 (14)	0.0041 (15)	0.0008 (17)
N1	0.029 (4)	0.064 (5)	0.030 (4)	−0.008 (4)	0.002 (3)	−0.010 (4)
N2	0.039 (4)	0.050 (5)	0.034 (4)	−0.006 (4)	0.006 (4)	−0.003 (4)

Geometric parameters (Å, º)

C1—C2	1.354 (14)	C8—N2	1.453 (10)
C1—C6	1.385 (12)	C8—C9	1.476 (10)
C1—Cl1	1.746 (9)	C8—H8A	0.9900
C2—C3	1.345 (12)	C8—H8B	0.9900
C2—H2	0.9500	C9—C10	1.486 (11)
C3—C4	1.392 (12)	C9—H9A	0.9900
C3—H3	0.9500	C9—H9B	0.9900
C4—C5	1.398 (13)	C10—H10A	0.9800
C4—S1	1.758 (8)	C10—H10B	0.9800
C5—C6	1.342 (11)	C10—H10C	0.9800
C5—H5	0.9500	O1—S1	1.430 (6)
C6—H6	0.9500	O2—S1	1.425 (6)
C7—O3	1.232 (12)	S1—N1	1.619 (7)
C7—N2	1.339 (10)	N1—H1N	0.8800
C7—N1	1.402 (10)	N2—H2N	0.8800
C2—C1—C6	120.9 (9)	H8A—C8—H8B	107.5
C2—C1—Cl1	119.0 (8)	C8—C9—C10	114.1 (7)
C6—C1—Cl1	120.1 (7)	C8—C9—H9A	108.7
C3—C2—C1	118.8 (9)	C10—C9—H9A	108.7
C3—C2—H2	120.6	C8—C9—H9B	108.7
C1—C2—H2	120.6	C10—C9—H9B	108.7
C2—C3—C4	121.6 (9)	H9A—C9—H9B	107.6
C2—C3—H3	119.2	C9—C10—H10A	109.5
C4—C3—H3	119.2	C9—C10—H10B	109.5
C3—C4—C5	118.8 (8)	H10A—C10—H10B	109.5
C3—C4—S1	120.8 (8)	C9—C10—H10C	109.5
C5—C4—S1	120.1 (7)	H10A—C10—H10C	109.5
C6—C5—C4	118.6 (9)	H10B—C10—H10C	109.5
C6—C5—H5	120.7	O2—S1—O1	120.2 (4)
C4—C5—H5	120.7	O2—S1—N1	110.2 (4)
C5—C6—C1	121.0 (9)	O1—S1—N1	104.5 (4)
C5—C6—H6	119.5	O2—S1—C4	107.3 (4)
C1—C6—H6	119.5	O1—S1—C4	107.7 (4)
O3—C7—N2	125.4 (8)	N1—S1—C4	106.1 (4)
O3—C7—N1	121.4 (8)	C7—N1—S1	125.7 (6)
N2—C7—N1	113.2 (9)	C7—N1—H1N	117.1
N2—C8—C9	115.4 (7)	S1—N1—H1N	117.1
N2—C8—H8A	108.4	C7—N2—C8	122.0 (8)
C9—C8—H8A	108.4	C7—N2—H2N	119.0
N2—C8—H8B	108.4	C8—N2—H2N	119.0
C9—C8—H8B	108.4
C6—C1—C2—C3	−5.0 (15)	C3—C4—S1—O1	−18.7 (8)
Cl1—C1—C2—C3	177.7 (7)	C5—C4—S1—O1	166.6 (6)
C1—C2—C3—C4	4.4 (14)	C3—C4—S1—N1	92.9 (7)
C2—C3—C4—C5	−4.2 (13)	C5—C4—S1—N1	−81.9 (7)
C2—C3—C4—S1	−179.0 (7)	O3—C7—N1—S1	11.0 (11)
C3—C4—C5—C6	4.7 (13)	N2—C7—N1—S1	−168.5 (5)
S1—C4—C5—C6	179.5 (7)	O2—S1—N1—C7	−40.4 (8)
C4—C5—C6—C1	−5.4 (13)	O1—S1—N1—C7	−170.9 (6)
C2—C1—C6—C5	5.7 (14)	C4—S1—N1—C7	75.4 (8)
Cl1—C1—C6—C5	−177.1 (7)	O3—C7—N2—C8	−0.5 (12)
N2—C8—C9—C10	175.0 (8)	N1—C7—N2—C8	179.1 (6)
C3—C4—S1—O2	−149.3 (7)	C9—C8—N2—C7	101.5 (10)
C5—C4—S1—O2	36.0 (8)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3^i	0.88	1.92	2.774 (9)	162
N2—H2N···O2^i	0.88	2.24	2.928 (10)	135
N2—H2N···O3^i	0.88	2.27	3.038 (9)	146
C10—H10A···O1^ii	0.98	2.58	3.404 (11)	142
C2—H2···Cl1^iii	0.95	2.84	3.643 (10)	143

Symmetry codes: (i) −x+1, −y+2, z−1/2; (ii) −x+1, −y+2, z+1/2; (iii) −x+1/2, y−1/2, z−1/2.

(acpa105) 4-chloro-N-((propylaminocarbonyl)benzenesulfonamide

Crystal data

C10H13ClN2O3S	Dx = 1.505 Mg m^−3
Mr = 276.73	Melting point: Kinetic phase transition K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 42 reflections
a = 26.657 (6) Å	θ = 10.2–12.5°
b = 5.0938 (16) Å	µ = 0.48 mm^−1
c = 8.9941 (18) Å	T = 105 K
V = 1221.3 (5) Å^3	Block, colourless
Z = 4	0.32 × 0.23 × 0.15 mm
F(000) = 576

Data collection

STOE STADI4 4-circle- diffractometer D094	2041 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.080
Planar graphite monochromator	θmax = 26.0°, θmin = 1.5°
ω/2θ scans	h = −32→32
Absorption correction: ψ scan X-RED (STOE & Cie, 1997)	k = −6→6
Tmin = 0.886, Tmax = 0.937	l = −11→11
2875 measured reflections	3 standard reflections every 240 min
2397 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.041	H-atom parameters constrained
wR(F^2) = 0.136	w = 1/[σ^2(Fo^2) + (0.044P)^2 + 4.5034P] where P = (Fo^2 + 2Fc^2)/3
S = 1.06	(Δ/σ)max < 0.001
2397 reflections	Δρmax = 0.30 e Å^−3
155 parameters	Δρmin = −0.45 e Å^−3
0 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.09 (15)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.04057 (17)	0.7650 (9)	0.4879 (5)	0.0205 (10)
C2	0.04432 (19)	0.6098 (10)	0.6137 (6)	0.0227 (10)
H2	0.0198	0.6207	0.6902	0.027*
C3	0.08455 (18)	0.4379 (9)	0.6261 (5)	0.0194 (10)
H3	0.0877	0.3269	0.7105	0.023*
C4	0.12016 (16)	0.4305 (8)	0.5130 (5)	0.0149 (9)
C5	0.11604 (18)	0.5885 (9)	0.3881 (5)	0.0189 (10)
H5	0.1405	0.5804	0.3115	0.023*
C6	0.07575 (18)	0.7582 (9)	0.3767 (5)	0.0212 (10)
H6	0.0725	0.8693	0.2925	0.025*
C7	0.24603 (16)	0.5712 (8)	0.5135 (5)	0.0154 (9)
C8	0.30770 (16)	0.9275 (8)	0.5357 (5)	0.0181 (9)
H8A	0.3059	1.0824	0.6020	0.022*
H8B	0.2944	0.9802	0.4373	0.022*
C9	0.36211 (17)	0.8460 (8)	0.5186 (6)	0.0207 (10)
H9A	0.3645	0.7016	0.4453	0.025*
H9B	0.3749	0.7803	0.6150	0.025*
C10	0.39415 (17)	1.0758 (9)	0.4672 (6)	0.0209 (10)
H10A	0.3828	1.1338	0.3688	0.031*
H10B	0.4293	1.0208	0.4615	0.031*
H10C	0.3909	1.2209	0.5381	0.031*
Cl2	−0.01067 (4)	0.9781 (3)	0.47166 (16)	0.0312 (3)
N1	0.21740 (14)	0.3908 (7)	0.5948 (4)	0.0153 (8)
H1N	0.2249	0.3714	0.6894	0.018*
N2	0.27601 (15)	0.7191 (8)	0.5966 (4)	0.0182 (8)
H2N	0.2769	0.6903	0.6930	0.022*
O1	0.16084 (12)	0.0305 (7)	0.6462 (3)	0.0199 (7)
O2	0.18368 (13)	0.1222 (6)	0.3841 (4)	0.0193 (7)
O3	0.24243 (12)	0.5862 (6)	0.3770 (4)	0.0184 (7)
S1	0.17148 (4)	0.2137 (2)	0.53002 (12)	0.0151 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.016 (2)	0.016 (2)	0.029 (3)	0.0010 (17)	−0.0059 (19)	−0.004 (2)
C2	0.017 (2)	0.029 (3)	0.022 (2)	−0.001 (2)	0.004 (2)	0.001 (2)
C3	0.019 (2)	0.023 (3)	0.017 (2)	−0.002 (2)	−0.0049 (19)	0.002 (2)
C4	0.014 (2)	0.014 (2)	0.017 (2)	−0.0009 (16)	−0.0048 (18)	−0.0053 (19)
C5	0.020 (2)	0.021 (2)	0.016 (2)	−0.003 (2)	0.0011 (19)	−0.001 (2)
C6	0.023 (3)	0.020 (3)	0.020 (2)	−0.002 (2)	−0.0040 (19)	0.002 (2)
C7	0.015 (2)	0.015 (2)	0.017 (2)	0.0028 (16)	−0.0005 (18)	−0.0023 (18)
C8	0.021 (2)	0.015 (2)	0.018 (2)	0.0001 (17)	−0.002 (2)	0.003 (2)
C9	0.022 (2)	0.017 (2)	0.023 (2)	0.0002 (18)	0.001 (2)	−0.001 (2)
C10	0.016 (2)	0.025 (2)	0.021 (2)	−0.0062 (18)	0.002 (2)	−0.001 (2)
Cl2	0.0229 (6)	0.0312 (6)	0.0395 (7)	0.0093 (5)	−0.0017 (6)	0.0010 (6)
N1	0.0145 (19)	0.0198 (18)	0.0117 (17)	−0.0031 (16)	0.0001 (15)	0.0028 (16)
N2	0.020 (2)	0.0216 (19)	0.0130 (17)	−0.0051 (17)	0.0009 (15)	−0.0004 (17)
O1	0.0244 (18)	0.0174 (16)	0.0178 (16)	−0.0044 (14)	0.0031 (13)	0.0040 (14)
O2	0.0248 (19)	0.0162 (15)	0.0169 (16)	−0.0056 (14)	0.0066 (14)	−0.0028 (13)
O3	0.0196 (18)	0.0197 (16)	0.0160 (16)	−0.0052 (14)	0.0007 (13)	0.0002 (14)
S1	0.0172 (5)	0.0136 (5)	0.0146 (5)	−0.0016 (4)	0.0023 (5)	0.0000 (5)

Geometric parameters (Å, º)

C1—C6	1.371 (7)	C8—N2	1.463 (6)
C1—C2	1.384 (7)	C8—C9	1.517 (6)
C1—Cl2	1.751 (5)	C8—H8A	0.9900
C2—C3	1.389 (7)	C8—H8B	0.9900
C2—H2	0.9500	C9—C10	1.521 (6)
C3—C4	1.392 (6)	C9—H9A	0.9900
C3—H3	0.9500	C9—H9B	0.9900
C4—C5	1.386 (6)	C10—H10A	0.9800
C4—S1	1.765 (4)	C10—H10B	0.9800
C5—C6	1.382 (7)	C10—H10C	0.9800
C5—H5	0.9500	N1—S1	1.628 (4)
C6—H6	0.9500	N1—H1N	0.8800
C7—O3	1.234 (6)	N2—H2N	0.8800
C7—N2	1.328 (6)	O1—S1	1.430 (3)
C7—N1	1.400 (6)	O2—S1	1.430 (3)
C6—C1—C2	122.2 (4)	H8A—C8—H8B	107.8
C6—C1—Cl2	119.2 (4)	C8—C9—C10	110.9 (4)
C2—C1—Cl2	118.6 (4)	C8—C9—H9A	109.5
C1—C2—C3	118.8 (4)	C10—C9—H9A	109.5
C1—C2—H2	120.6	C8—C9—H9B	109.5
C3—C2—H2	120.6	C10—C9—H9B	109.5
C2—C3—C4	119.0 (4)	H9A—C9—H9B	108.0
C2—C3—H3	120.5	C9—C10—H10A	109.5
C4—C3—H3	120.5	C9—C10—H10B	109.5
C5—C4—C3	121.5 (4)	H10A—C10—H10B	109.5
C5—C4—S1	119.7 (3)	C9—C10—H10C	109.5
C3—C4—S1	118.8 (3)	H10A—C10—H10C	109.5
C6—C5—C4	119.0 (4)	H10B—C10—H10C	109.5
C6—C5—H5	120.5	C7—N1—S1	125.9 (3)
C4—C5—H5	120.5	C7—N1—H1N	117.0
C1—C6—C5	119.6 (4)	S1—N1—H1N	117.0
C1—C6—H6	120.2	C7—N2—C8	123.3 (4)
C5—C6—H6	120.2	C7—N2—H2N	118.4
O3—C7—N2	124.8 (4)	C8—N2—H2N	118.4
O3—C7—N1	121.2 (4)	O1—S1—O2	120.2 (2)
N2—C7—N1	114.0 (4)	O1—S1—N1	104.4 (2)
N2—C8—C9	113.0 (4)	O2—S1—N1	109.8 (2)
N2—C8—H8A	109.0	O1—S1—C4	108.5 (2)
C9—C8—H8A	109.0	O2—S1—C4	107.5 (2)
N2—C8—H8B	109.0	N1—S1—C4	105.5 (2)
C9—C8—H8B	109.0
C6—C1—C2—C3	−1.3 (7)	O3—C7—N2—C8	2.2 (7)
Cl2—C1—C2—C3	179.1 (4)	N1—C7—N2—C8	−177.4 (4)
C1—C2—C3—C4	1.1 (7)	C9—C8—N2—C7	−101.1 (5)
C2—C3—C4—C5	−0.7 (7)	C7—N1—S1—O1	169.8 (4)
C2—C3—C4—S1	179.4 (4)	C7—N1—S1—O2	39.7 (4)
C3—C4—C5—C6	0.5 (7)	C7—N1—S1—C4	−75.9 (4)
S1—C4—C5—C6	−179.7 (4)	C5—C4—S1—O1	−165.7 (3)
C2—C1—C6—C5	1.1 (7)	C3—C4—S1—O1	14.2 (4)
Cl2—C1—C6—C5	−179.3 (4)	C5—C4—S1—O2	−34.3 (4)
C4—C5—C6—C1	−0.6 (7)	C3—C4—S1—O2	145.6 (3)
N2—C8—C9—C10	−175.3 (4)	C5—C4—S1—N1	82.8 (4)
O3—C7—N1—S1	−9.4 (6)	C3—C4—S1—N1	−97.3 (4)
N2—C7—N1—S1	170.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3^i	0.88	1.91	2.757 (5)	161
N2—H2N···O2^i	0.88	2.23	2.915 (5)	135
N2—H2N···O3^i	0.88	2.23	3.003 (5)	146
C10—H10A···O1^ii	0.98	2.46	3.282 (6)	141

Symmetry codes: (i) −x+1/2, −y+1, z+1/2; (ii) −x+1/2, −y+1, z−1/2.

(acpa200) 4-chloro-N-((propylaminocarbonyl)benzenesulfonamide

Crystal data

C10H13ClN2O3S	Dx = 1.482 Mg m^−3
Mr = 276.73	Melting point: Kinetic phase transition K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 42 reflections
a = 26.675 (5) Å	θ = 10.2–12.4°
b = 5.1438 (14) Å	µ = 0.47 mm^−1
c = 9.0370 (16) Å	T = 200 K
V = 1240.0 (5) Å^3	Block, colourless
Z = 4	0.32 × 0.23 × 0.15 mm
F(000) = 576

Data collection

STOE STADI4 4-circle- diffractometer D094	1794 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.029
Planar graphite monochromator	θmax = 25.0°, θmin = 1.5°
ω/2θ scans	h = −31→31
Absorption correction: ψ scan X-RED (STOE & Cie, 1997)	k = −6→6
Tmin = 0.886, Tmax = 0.937	l = −10→10
2631 measured reflections	3 standard reflections every 240 min
2181 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.039	H-atom parameters constrained
wR(F^2) = 0.092	w = 1/[σ^2(Fo^2) + (0.0185P)^2 + 1.3649P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max < 0.001
2181 reflections	Δρmax = 0.28 e Å^−3
155 parameters	Δρmin = −0.27 e Å^−3
0 restraints	Absolute structure: Flack (1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.00 (12)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.04098 (13)	0.7625 (8)	0.4873 (5)	0.0365 (10)
C2	0.04511 (15)	0.6097 (9)	0.6116 (5)	0.0400 (11)
H2	0.0206	0.6195	0.6877	0.048*
C3	0.08521 (14)	0.4423 (8)	0.6246 (4)	0.0349 (10)
H3	0.0887	0.3348	0.7095	0.042*
C4	0.12045 (12)	0.4333 (7)	0.5115 (4)	0.0266 (8)
C5	0.11629 (14)	0.5876 (8)	0.3880 (4)	0.0326 (9)
H5	0.1408	0.5782	0.3119	0.039*
C6	0.07612 (14)	0.7570 (8)	0.3752 (4)	0.0358 (10)
H6	0.0729	0.8668	0.2912	0.043*
C7	0.24662 (13)	0.5725 (7)	0.5115 (4)	0.0255 (8)
C8	0.30770 (12)	0.9249 (7)	0.5337 (4)	0.0299 (8)
H8A	0.3055	1.0791	0.5990	0.036*
H8B	0.2943	0.9750	0.4356	0.036*
C9	0.36215 (13)	0.8489 (7)	0.5170 (5)	0.0350 (10)
H9A	0.3650	0.7055	0.4444	0.042*
H9B	0.3750	0.7853	0.6131	0.042*
C10	0.39367 (14)	1.0772 (8)	0.4656 (5)	0.0399 (10)
H10A	0.3818	1.1358	0.3685	0.060*
H10B	0.4288	1.0235	0.4582	0.060*
H10C	0.3907	1.2198	0.5370	0.060*
Cl2	−0.00988 (4)	0.9747 (2)	0.47081 (16)	0.0594 (4)
N1	0.21786 (11)	0.3923 (6)	0.5928 (3)	0.0267 (7)
H1N	0.2255	0.3725	0.6869	0.032*
N2	0.27650 (11)	0.7181 (6)	0.5949 (3)	0.0309 (8)
H2N	0.2775	0.6887	0.6908	0.037*
O1	0.16118 (9)	0.0364 (5)	0.6441 (3)	0.0337 (6)
O2	0.18410 (10)	0.1257 (5)	0.3833 (3)	0.0323 (7)
O3	0.24284 (10)	0.5855 (5)	0.3758 (3)	0.0329 (7)
S1	0.17194 (3)	0.21785 (17)	0.52852 (10)	0.0262 (2)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.0237 (18)	0.038 (2)	0.048 (3)	0.0004 (18)	−0.0058 (18)	−0.005 (2)
C2	0.028 (2)	0.053 (3)	0.039 (2)	0.003 (2)	0.0058 (19)	0.000 (2)
C3	0.031 (2)	0.045 (3)	0.029 (2)	−0.001 (2)	−0.0013 (17)	0.006 (2)
C4	0.0228 (18)	0.032 (2)	0.025 (2)	−0.0041 (16)	−0.0036 (16)	−0.0020 (18)
C5	0.032 (2)	0.035 (2)	0.030 (2)	−0.0054 (19)	0.0014 (18)	−0.001 (2)
C6	0.034 (2)	0.037 (2)	0.037 (2)	−0.002 (2)	−0.0040 (18)	0.008 (2)
C7	0.0194 (17)	0.0267 (19)	0.031 (2)	0.0043 (15)	0.0010 (15)	−0.0009 (18)
C8	0.0290 (19)	0.029 (2)	0.031 (2)	−0.0083 (16)	−0.0016 (18)	0.000 (2)
C9	0.029 (2)	0.033 (2)	0.042 (2)	−0.0010 (16)	0.0045 (19)	0.000 (2)
C10	0.034 (2)	0.042 (2)	0.043 (2)	−0.0133 (18)	0.003 (2)	−0.001 (2)
Cl2	0.0395 (6)	0.0604 (8)	0.0784 (9)	0.0171 (6)	−0.0030 (6)	0.0026 (8)
N1	0.0240 (16)	0.0350 (18)	0.0212 (15)	−0.0050 (15)	−0.0017 (13)	0.0022 (14)
N2	0.0283 (17)	0.0400 (19)	0.0245 (15)	−0.0106 (16)	−0.0019 (13)	−0.0014 (16)
O1	0.0340 (15)	0.0321 (15)	0.0349 (15)	−0.0048 (13)	0.0028 (12)	0.0073 (13)
O2	0.0365 (16)	0.0312 (15)	0.0291 (14)	−0.0061 (13)	0.0058 (12)	−0.0065 (12)
O3	0.0386 (16)	0.0379 (16)	0.0221 (14)	−0.0084 (13)	0.0018 (12)	−0.0009 (13)
S1	0.0255 (4)	0.0263 (5)	0.0269 (4)	−0.0031 (4)	0.0015 (4)	0.0002 (4)

Geometric parameters (Å, º)

C1—C2	1.376 (6)	C8—N2	1.460 (5)
C1—C6	1.380 (5)	C8—C9	1.512 (5)
C1—Cl2	1.747 (4)	C8—H8A	0.9900
C2—C3	1.378 (5)	C8—H8B	0.9900
C2—H2	0.9500	C9—C10	1.517 (5)
C3—C4	1.390 (5)	C9—H9A	0.9900
C3—H3	0.9500	C9—H9B	0.9900
C4—C5	1.373 (5)	C10—H10A	0.9800
C4—S1	1.772 (4)	C10—H10B	0.9800
C5—C6	1.386 (5)	C10—H10C	0.9800
C5—H5	0.9500	N1—S1	1.626 (3)
C6—H6	0.9500	N1—H1N	0.8800
C7—O3	1.232 (4)	N2—H2N	0.8800
C7—N2	1.329 (5)	O1—S1	1.430 (3)
C7—N1	1.410 (4)	O2—S1	1.433 (3)
C2—C1—C6	122.2 (4)	H8A—C8—H8B	107.7
C2—C1—Cl2	119.2 (3)	C8—C9—C10	111.3 (3)
C6—C1—Cl2	118.5 (3)	C8—C9—H9A	109.4
C1—C2—C3	119.3 (4)	C10—C9—H9A	109.4
C1—C2—H2	120.4	C8—C9—H9B	109.4
C3—C2—H2	120.4	C10—C9—H9B	109.4
C2—C3—C4	118.9 (4)	H9A—C9—H9B	108.0
C2—C3—H3	120.6	C9—C10—H10A	109.5
C4—C3—H3	120.6	C9—C10—H10B	109.5
C5—C4—C3	121.6 (4)	H10A—C10—H10B	109.5
C5—C4—S1	119.6 (3)	C9—C10—H10C	109.5
C3—C4—S1	118.7 (3)	H10A—C10—H10C	109.5
C4—C5—C6	119.6 (4)	H10B—C10—H10C	109.5
C4—C5—H5	120.2	C7—N1—S1	125.9 (3)
C6—C5—H5	120.2	C7—N1—H1N	117.0
C1—C6—C5	118.5 (4)	S1—N1—H1N	117.0
C1—C6—H6	120.8	C7—N2—C8	122.5 (3)
C5—C6—H6	120.8	C7—N2—H2N	118.7
O3—C7—N2	125.7 (4)	C8—N2—H2N	118.7
O3—C7—N1	120.7 (4)	O1—S1—O2	119.90 (16)
N2—C7—N1	113.6 (3)	O1—S1—N1	104.51 (16)
N2—C8—C9	113.4 (3)	O2—S1—N1	109.84 (16)
N2—C8—H8A	108.9	O1—S1—C4	108.44 (16)
C9—C8—H8A	108.9	O2—S1—C4	107.63 (16)
N2—C8—H8B	108.9	N1—S1—C4	105.65 (16)
C9—C8—H8B	108.9
C6—C1—C2—C3	−0.9 (6)	O3—C7—N2—C8	2.8 (6)
Cl2—C1—C2—C3	180.0 (3)	N1—C7—N2—C8	−177.1 (3)
C1—C2—C3—C4	0.2 (6)	C9—C8—N2—C7	−102.0 (4)
C2—C3—C4—C5	0.3 (6)	C7—N1—S1—O1	170.0 (3)
C2—C3—C4—S1	−180.0 (3)	C7—N1—S1—O2	40.1 (3)
C3—C4—C5—C6	0.1 (6)	C7—N1—S1—C4	−75.7 (3)
S1—C4—C5—C6	−179.7 (3)	C5—C4—S1—O1	−165.4 (3)
C2—C1—C6—C5	1.3 (6)	C3—C4—S1—O1	14.9 (3)
Cl2—C1—C6—C5	−179.6 (3)	C5—C4—S1—O2	−34.3 (3)
C4—C5—C6—C1	−0.8 (6)	C3—C4—S1—O2	146.0 (3)
N2—C8—C9—C10	−175.1 (3)	C5—C4—S1—N1	83.0 (3)
O3—C7—N1—S1	−9.8 (5)	C3—C4—S1—N1	−96.7 (3)
N2—C7—N1—S1	170.1 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3^i	0.88	1.92	2.767 (4)	162
N2—H2N···O2^i	0.88	2.23	2.923 (4)	135
N2—H2N···O3^i	0.88	2.25	3.025 (4)	146
C10—H10A···O1^ii	0.98	2.49	3.305 (5)	140

Symmetry codes: (i) −x+1/2, −y+1, z+1/2; (ii) −x+1/2, −y+1, z−1/2.

(acpa295) 4-chloro-N-((propylaminocarbonyl)benzenesulfonamide

Crystal data

C10H13ClN2O3S	Dx = 1.450 Mg m^−3
Mr = 276.73	Melting point: Kinetic phase transition K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 42 reflections
a = 26.673 (6) Å	θ = 10.1–12.4°
b = 5.2296 (19) Å	µ = 0.46 mm^−1
c = 9.088 (2) Å	T = 295 K
V = 1267.6 (6) Å^3	Block, colourless
Z = 4	0.32 × 0.23 × 0.15 mm
F(000) = 576

Data collection

STOE STADI4 4-circle- diffractometer D094	1828 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.024
Planar graphite monochromator	θmax = 26.0°, θmin = 1.5°
ω/2θ scans	h = −32→32
Absorption correction: ψ scan X-RED (STOE & Cie, 1997)	k = −6→6
Tmin = 0.888, Tmax = 0.937	l = −11→11
2974 measured reflections	3 standard reflections every 240 min
2485 independent reflections	intensity decay: none

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.051	H-atom parameters constrained
wR(F^2) = 0.116	w = 1/[σ^2(Fo^2) + (0.026P)^2 + 1.143P] where P = (Fo^2 + 2Fc^2)/3
S = 1.13	(Δ/σ)max < 0.001
2485 reflections	Δρmax = 0.22 e Å^−3
155 parameters	Δρmin = −0.25 e Å^−3
0 restraints	Absolute structure: Flack(1983)
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.01 (14)

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.04134 (16)	0.7577 (10)	0.4852 (6)	0.0599 (12)
C2	0.04595 (18)	0.6082 (12)	0.6068 (6)	0.0715 (16)
H2	0.0221	0.6172	0.6813	0.086*
C3	0.08588 (17)	0.4440 (11)	0.6195 (5)	0.0621 (14)
H3	0.0893	0.3409	0.7023	0.075*
C4	0.12092 (14)	0.4337 (8)	0.5080 (5)	0.0425 (10)
C5	0.11670 (18)	0.5867 (9)	0.3863 (5)	0.0553 (13)
H5	0.1408	0.5797	0.3123	0.066*
C6	0.07630 (17)	0.7521 (11)	0.3741 (6)	0.0628 (13)
H6	0.0729	0.8575	0.2923	0.075*
C7	0.24719 (15)	0.5709 (8)	0.5064 (5)	0.0435 (10)
C8	0.30763 (15)	0.9228 (9)	0.5286 (6)	0.0552 (12)
H8A	0.3044	1.0713	0.5918	0.066*
H8B	0.2948	0.9686	0.4323	0.066*
C9	0.36164 (16)	0.8561 (9)	0.5148 (6)	0.0637 (14)
H9A	0.3654	0.7160	0.4457	0.076*
H9B	0.3743	0.7999	0.6095	0.076*
C10	0.39204 (18)	1.0838 (10)	0.4620 (6)	0.0728 (15)
H10A	0.3829	1.1239	0.3624	0.109*
H10B	0.4271	1.0430	0.4662	0.109*
H10C	0.3853	1.2285	0.5239	0.109*
Cl1	−0.00955 (5)	0.9650 (3)	0.4699 (2)	0.1027 (6)
N1	0.21862 (12)	0.3964 (7)	0.5877 (4)	0.0451 (9)
H1N	0.2260	0.3789	0.6792	0.054*
N2	0.27721 (13)	0.7150 (8)	0.5888 (4)	0.0535 (10)
H2N	0.2788	0.6845	0.6817	0.064*
O1	0.16186 (11)	0.0467 (6)	0.6399 (3)	0.0569 (8)
O2	0.18440 (12)	0.1334 (6)	0.3805 (3)	0.0541 (8)
O3	0.24322 (11)	0.5857 (6)	0.3723 (3)	0.0546 (9)
S1	0.17258 (4)	0.2238 (2)	0.52455 (11)	0.0443 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.042 (2)	0.063 (3)	0.075 (3)	0.003 (2)	−0.005 (2)	−0.008 (3)
C2	0.047 (3)	0.103 (5)	0.065 (3)	0.007 (3)	0.012 (3)	0.004 (3)
C3	0.050 (3)	0.086 (4)	0.050 (3)	0.005 (3)	0.006 (2)	0.012 (3)
C4	0.038 (2)	0.047 (2)	0.042 (2)	−0.0069 (18)	−0.0036 (18)	0.000 (2)
C5	0.056 (3)	0.060 (3)	0.050 (3)	−0.004 (3)	0.004 (2)	0.002 (3)
C6	0.059 (3)	0.066 (3)	0.063 (3)	0.006 (3)	−0.008 (2)	0.008 (3)
C7	0.038 (2)	0.047 (2)	0.046 (3)	0.0018 (19)	0.0040 (19)	0.001 (2)
C8	0.053 (3)	0.057 (3)	0.055 (3)	−0.006 (2)	−0.005 (2)	0.004 (3)
C9	0.051 (3)	0.067 (3)	0.073 (3)	−0.005 (2)	0.010 (3)	0.001 (3)
C10	0.063 (3)	0.083 (4)	0.073 (3)	−0.031 (3)	0.005 (3)	−0.004 (3)
Cl1	0.0672 (9)	0.1038 (13)	0.1372 (15)	0.0295 (9)	−0.0049 (10)	0.0063 (13)
N1	0.0406 (19)	0.058 (2)	0.0372 (19)	−0.0097 (18)	−0.0017 (15)	0.0028 (17)
N2	0.050 (2)	0.066 (3)	0.044 (2)	−0.020 (2)	−0.0026 (17)	0.003 (2)
O1	0.061 (2)	0.0532 (18)	0.0564 (19)	−0.0133 (17)	0.0046 (16)	0.0114 (16)
O2	0.061 (2)	0.0540 (19)	0.0474 (17)	−0.0066 (16)	0.0067 (15)	−0.0120 (15)
O3	0.062 (2)	0.062 (2)	0.0398 (17)	−0.0138 (17)	0.0025 (15)	0.0000 (17)
S1	0.0439 (5)	0.0462 (6)	0.0427 (5)	−0.0066 (5)	0.0023 (5)	0.0005 (5)

Geometric parameters (Å, º)

C1—C2	1.360 (7)	C8—N2	1.462 (5)
C1—C6	1.374 (6)	C8—C9	1.488 (6)
C1—Cl1	1.743 (5)	C8—H8A	0.9700
C2—C3	1.373 (7)	C8—H8B	0.9700
C2—H2	0.9300	C9—C10	1.519 (6)
C3—C4	1.380 (6)	C9—H9A	0.9700
C3—H3	0.9300	C9—H9B	0.9700
C4—C5	1.370 (6)	C10—H10A	0.9600
C4—S1	1.768 (4)	C10—H10B	0.9600
C5—C6	1.386 (6)	C10—H10C	0.9600
C5—H5	0.9300	N1—S1	1.629 (3)
C6—H6	0.9300	N1—H1N	0.8600
C7—O3	1.225 (5)	N2—H2N	0.8600
C7—N2	1.330 (5)	O1—S1	1.428 (3)
C7—N1	1.400 (5)	O2—S1	1.427 (3)
C2—C1—C6	121.6 (4)	H8A—C8—H8B	107.7
C2—C1—Cl1	119.5 (4)	C8—C9—C10	111.1 (4)
C6—C1—Cl1	118.9 (4)	C8—C9—H9A	109.4
C1—C2—C3	119.9 (5)	C10—C9—H9A	109.4
C1—C2—H2	120.1	C8—C9—H9B	109.4
C3—C2—H2	120.1	C10—C9—H9B	109.4
C2—C3—C4	119.2 (5)	H9A—C9—H9B	108.0
C2—C3—H3	120.4	C9—C10—H10A	109.5
C4—C3—H3	120.4	C9—C10—H10B	109.5
C5—C4—C3	121.0 (4)	H10A—C10—H10B	109.5
C5—C4—S1	119.7 (3)	C9—C10—H10C	109.5
C3—C4—S1	119.3 (3)	H10A—C10—H10C	109.5
C4—C5—C6	119.5 (4)	H10B—C10—H10C	109.5
C4—C5—H5	120.2	C7—N1—S1	125.9 (3)
C6—C5—H5	120.2	C7—N1—H1N	117.1
C1—C6—C5	118.8 (5)	S1—N1—H1N	117.1
C1—C6—H6	120.6	C7—N2—C8	123.0 (4)
C5—C6—H6	120.6	C7—N2—H2N	118.5
O3—C7—N2	125.2 (4)	C8—N2—H2N	118.5
O3—C7—N1	121.3 (4)	O2—S1—O1	120.2 (2)
N2—C7—N1	113.6 (4)	O2—S1—N1	109.89 (18)
N2—C8—C9	113.3 (4)	O1—S1—N1	104.59 (18)
N2—C8—H8A	108.9	O2—S1—C4	107.44 (19)
C9—C8—H8A	108.9	O1—S1—C4	108.0 (2)
N2—C8—H8B	108.9	N1—S1—C4	105.86 (18)
C9—C8—H8B	108.9
C6—C1—C2—C3	−1.0 (8)	O3—C7—N2—C8	3.7 (7)
Cl1—C1—C2—C3	179.9 (4)	N1—C7—N2—C8	−175.3 (4)
C1—C2—C3—C4	0.1 (8)	C9—C8—N2—C7	−104.1 (5)
C2—C3—C4—C5	0.8 (8)	C7—N1—S1—O2	39.5 (4)
C2—C3—C4—S1	179.6 (4)	C7—N1—S1—O1	169.8 (3)
C3—C4—C5—C6	−0.8 (7)	C7—N1—S1—C4	−76.2 (4)
S1—C4—C5—C6	−179.6 (4)	C5—C4—S1—O2	−35.1 (4)
C2—C1—C6—C5	1.0 (8)	C3—C4—S1—O2	146.0 (4)
Cl1—C1—C6—C5	−179.9 (4)	C5—C4—S1—O1	−166.2 (3)
C4—C5—C6—C1	−0.1 (7)	C3—C4—S1—O1	15.0 (4)
N2—C8—C9—C10	−176.1 (4)	C5—C4—S1—N1	82.2 (4)
O3—C7—N1—S1	−8.8 (6)	C3—C4—S1—N1	−96.6 (4)
N2—C7—N1—S1	170.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O3^i	0.86	1.95	2.781 (5)	164
N2—H2N···O2^i	0.86	2.27	2.950 (5)	137
N2—H2N···O3^i	0.86	2.31	3.067 (5)	147
C10—H10A···O1^ii	0.96	2.51	3.332 (6)	143

Symmetry codes: (i) −x+1/2, −y+1, z+1/2; (ii) −x+1/2, −y+1, z−1/2.