Methyl 5-chloro-2-[N-(3-eth­oxy­carbonyl­prop­yl)-4-methyl­benzene­sulfonamido]­benzoate

Wang, B.; Jia, R.; Shi, Y.-B.; He, F.-F.; Wang, H.-B.

doi:10.1107/S1600536810023792

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 7| July 2010| Page o1819

doi:10.1107/S1600536810023792

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Methyl 5-chloro-2-[N-(3-ethoxycarbonylpropyl)-4-methylbenzenesulfonamido]benzoate

Bin Wang,^a,^b Ru Jia,^a Ya-Bin Shi,^a,^b Fei-Fei He ^a,^b and Hai-Bo Wang ^a ^*

^aCollege of Food Science and Light Industry, Nanjing University of Technology, Xinmofan Road No.5 Nanjing, Nanjing 210009, People's Republic of China, and ^bCollege of Science, Nanjing University of Technology, Xinmofan Road No.5 Nanjing, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: wanghaibo@njut.edu.cn

(Received 7 June 2010; accepted 19 June 2010; online 26 June 2010)

In the title compound, C₂₁H₂₄ClNO₆S, the benzene rings are oriented at a dihedral angles of 41.6 (2)°. In the crystal structure, weak intermolecular C—H⋯O interactions link the molecules.

Related literature

For the preparation of the title compound, see: Kondo et al. (1999 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₁H₂₄ClNO₆S
M_r = 453.92
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.1480 (18) Å
b = 10.742 (2) Å
c = 23.258 (5) Å
V = 2285.5 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 296 K
0.30 × 0.10 × 0.05 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.917, T_max = 0.985
4623 measured reflections
4130 independent reflections
2134 reflections with I > 2σ(I)
R_int = 0.072
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.114
S = 0.92
4130 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.21 e Å⁻³
Absolute structure: Flack (1983 ), 1748 Friedel pairs
Flack parameter: 0.03 (12)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11A⋯O3ⁱ	0.93	2.55	3.275 (6)	135
C14—H14A⋯O2ⁱⁱ	0.96	2.60	3.338 (7)	134
C17—H17A⋯O2ⁱⁱⁱ	0.93	2.59	3.414 (8)	148
Symmetry codes: (i) $[-x, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x, y+1, z; (iii) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989 ); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810023792/bq2221sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810023792/bq2221Isup2.hkl

checkCIF report

Comment top

Quinolines are a major class of alkaloids and play an important role in the fields of natural products and medicinal chemistry. The title compound, (I), is a useful intermediate. (Kondo et al., 1999). In the molecule of the title compound (Fig. 1), the bond lengths (Allen et al., 1987) and angles are within normal ranges. The intramolecular C-H···O hydrogen bond (Table 1) results in the formation of a five-membered ring C (C6/H6A/O4/S/N). Rings A(C7-C12) and B(C15-C20) are planar with maximum deviations of 0.011 (4) Å for C9 and -0.021 (5) Å for C16, respectively. The dihedral angle between these rings is 41.6 (2) °. In the crystal structure, intermolecular weak C-H..O interactions link the molecules to form a stable structure.

Related literature top

For the preparation of the title compound, see: Kondo et al. (1999). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound, (I) was prepared by the literature method (Kondo et al., 1999). Crystals suitable for X-ray analysis were obtained by slow evaporation of an methanol solution.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1989); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top

Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.

Methyl 5-chloro-2-[N-(3-ethoxycarbonylpropyl)- 4-methylbenzenesulfonamido]benzoate top

Crystal data top

C₂₁H₂₄ClNO₆S	D_x = 1.319 Mg m⁻³
M_r = 453.92	Melting point: 353 K
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 25 reflections
a = 9.1480 (18) Å	θ = 8–12°
b = 10.742 (2) Å	µ = 0.29 mm⁻¹
c = 23.258 (5) Å	T = 296 K
V = 2285.5 (8) Å³	Needle, colorless
Z = 4	0.30 × 0.10 × 0.05 mm
F(000) = 952

Data collection top

Enraf–Nonius CAD-4 diffractometer	2134 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.072
Graphite monochromator	θ_max = 25.3°, θ_min = 1.8°
ω/2θ scans	h = −10→0
Absorption correction: ψ scan (North et al., 1968)	k = −12→0
T_min = 0.917, T_max = 0.985	l = −27→27
4623 measured reflections	3 standard reflections every 200 reflections
4130 independent reflections	intensity decay: 1%

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.063	H-atom parameters constrained
wR(F²) = 0.114	w = 1/[σ²(F_o²) + (0.025P)²] where P = (F_o² + 2F_c²)/3
S = 0.92	(Δ/σ)_max < 0.001
4130 reflections	Δρ_max = 0.19 e Å⁻³
271 parameters	Δρ_min = −0.21 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 1748 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.03 (12)

Crystal data top

C₂₁H₂₄ClNO₆S	V = 2285.5 (8) Å³
M_r = 453.92	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.1480 (18) Å	µ = 0.29 mm⁻¹
b = 10.742 (2) Å	T = 296 K
c = 23.258 (5) Å	0.30 × 0.10 × 0.05 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	2134 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.072
T_min = 0.917, T_max = 0.985	3 standard reflections every 200 reflections
4623 measured reflections	intensity decay: 1%
4130 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	H-atom parameters constrained
wR(F²) = 0.114	Δρ_max = 0.19 e Å⁻³
S = 0.92	Δρ_min = −0.21 e Å⁻³
4130 reflections	Absolute structure: Flack (1983), 1748 Friedel pairs
271 parameters	Absolute structure parameter: 0.03 (12)
0 restraints

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(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
S	0.32206 (15)	0.97963 (12)	0.21916 (6)	0.0523 (4)
Cl	−0.34814 (14)	1.01035 (14)	0.35104 (7)	0.0753 (5)
O1	0.5372 (6)	0.6826 (5)	0.4389 (3)	0.130 (2)
O2	0.3409 (6)	0.5726 (4)	0.4257 (2)	0.1119 (19)
O3	0.2927 (4)	1.1049 (3)	0.23835 (15)	0.0605 (11)
O4	0.4681 (4)	0.9398 (3)	0.21051 (16)	0.0668 (12)
O5	0.1790 (4)	1.2067 (3)	0.35132 (15)	0.0537 (9)
O6	0.3165 (4)	1.0402 (3)	0.37290 (16)	0.0651 (11)
N	0.2482 (4)	0.8844 (3)	0.26778 (18)	0.0459 (12)
C1	0.6798 (12)	0.6647 (8)	0.5254 (4)	0.165 (4)
H1A	0.6820	0.6204	0.5613	0.247*
H1B	0.6714	0.7524	0.5328	0.247*
H1C	0.7684	0.6487	0.5045	0.247*
C2	0.5609 (11)	0.6252 (9)	0.4933 (4)	0.145 (4)
H2A	0.4737	0.6372	0.5163	0.174*
H2B	0.5713	0.5363	0.4869	0.174*
C3	0.4202 (8)	0.6527 (6)	0.4104 (3)	0.077 (2)
C4	0.4113 (6)	0.7278 (5)	0.3548 (3)	0.0671 (17)
H4B	0.3982	0.8152	0.3641	0.080*
H4C	0.5023	0.7193	0.3338	0.080*
C5	0.2883 (6)	0.6854 (5)	0.3181 (2)	0.0570 (16)
H5A	0.1971	0.6994	0.3384	0.068*
H5B	0.2978	0.5966	0.3116	0.068*
C6	0.2816 (6)	0.7504 (4)	0.2610 (2)	0.0553 (16)
H6A	0.3746	0.7411	0.2415	0.066*
H6B	0.2069	0.7118	0.2374	0.066*
C7	0.1045 (6)	0.9196 (4)	0.2868 (2)	0.0452 (13)
C8	0.0844 (5)	1.0121 (4)	0.3272 (2)	0.0412 (12)
C9	−0.0552 (5)	1.0403 (5)	0.3460 (2)	0.0543 (15)
H9A	−0.0678	1.1043	0.3725	0.065*
C10	−0.1762 (6)	0.9764 (4)	0.3267 (2)	0.0549 (14)
C11	−0.1565 (6)	0.8815 (5)	0.2868 (3)	0.0610 (16)
H11A	−0.2360	0.8361	0.2734	0.073*
C12	−0.0171 (6)	0.8557 (5)	0.2676 (3)	0.0562 (16)
H12A	−0.0045	0.7927	0.2405	0.067*
C13	0.2085 (6)	1.0834 (4)	0.3535 (2)	0.0476 (13)
C14	0.2962 (6)	1.2856 (5)	0.3736 (3)	0.080 (2)
H14A	0.2676	1.3714	0.3709	0.120*
H14B	0.3834	1.2724	0.3514	0.120*
H14C	0.3147	1.2648	0.4131	0.120*
C15	0.2247 (6)	0.9560 (5)	0.1556 (2)	0.0558 (15)
C16	0.0987 (6)	1.0246 (6)	0.1445 (3)	0.0737 (18)
H16A	0.0677	1.0842	0.1708	0.088*
C17	0.0199 (7)	1.0052 (7)	0.0952 (3)	0.082 (2)
H17A	−0.0607	1.0549	0.0870	0.098*
C18	0.0601 (7)	0.9126 (7)	0.0581 (3)	0.074 (2)
C19	0.1794 (8)	0.8414 (6)	0.0698 (3)	0.078 (2)
H19A	0.2045	0.7768	0.0451	0.094*
C20	0.2628 (7)	0.8637 (6)	0.1175 (2)	0.0659 (18)
H20A	0.3460	0.8160	0.1242	0.079*
C21	−0.0298 (8)	0.8910 (8)	0.0048 (3)	0.132 (3)
H21A	−0.1074	0.9511	0.0032	0.198*
H21B	−0.0705	0.8087	0.0059	0.198*
H21C	0.0311	0.8995	−0.0285	0.198*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.0493 (8)	0.0417 (7)	0.0659 (10)	−0.0006 (8)	0.0099 (8)	0.0019 (8)
Cl	0.0481 (8)	0.0653 (10)	0.1124 (13)	−0.0118 (8)	0.0152 (9)	−0.0006 (10)
O1	0.139 (5)	0.116 (4)	0.134 (5)	−0.032 (4)	−0.076 (4)	0.041 (4)
O2	0.134 (5)	0.089 (4)	0.113 (4)	−0.045 (4)	−0.014 (4)	0.026 (3)
O3	0.084 (3)	0.0296 (18)	0.068 (3)	0.002 (2)	0.012 (2)	−0.0045 (17)
O4	0.054 (2)	0.063 (3)	0.083 (3)	−0.006 (2)	0.017 (2)	−0.006 (2)
O5	0.046 (2)	0.0352 (18)	0.080 (3)	−0.0061 (18)	−0.001 (2)	−0.0094 (19)
O6	0.056 (2)	0.051 (2)	0.088 (3)	0.009 (2)	−0.016 (2)	−0.007 (2)
N	0.055 (3)	0.031 (2)	0.051 (3)	0.000 (2)	0.014 (2)	0.001 (2)
C1	0.192 (12)	0.155 (9)	0.148 (9)	−0.042 (9)	−0.011 (9)	−0.002 (7)
C2	0.163 (10)	0.136 (8)	0.138 (9)	−0.013 (8)	−0.045 (8)	0.033 (7)
C3	0.087 (6)	0.056 (4)	0.087 (5)	−0.010 (4)	−0.028 (5)	−0.004 (4)
C4	0.070 (4)	0.041 (3)	0.090 (5)	0.008 (3)	−0.011 (4)	0.007 (4)
C5	0.057 (4)	0.039 (3)	0.075 (4)	0.002 (3)	−0.005 (3)	0.004 (3)
C6	0.068 (4)	0.029 (3)	0.070 (4)	0.013 (3)	0.007 (3)	−0.001 (3)
C7	0.046 (3)	0.033 (3)	0.056 (4)	0.000 (3)	0.005 (3)	0.007 (3)
C8	0.034 (3)	0.030 (3)	0.060 (3)	−0.008 (3)	0.003 (2)	0.004 (3)
C9	0.046 (3)	0.040 (3)	0.077 (4)	−0.004 (3)	−0.006 (3)	0.006 (3)
C10	0.050 (3)	0.039 (3)	0.076 (4)	−0.007 (3)	0.002 (3)	0.003 (3)
C11	0.052 (4)	0.051 (3)	0.080 (4)	0.000 (3)	−0.011 (4)	0.003 (3)
C12	0.057 (4)	0.039 (3)	0.072 (5)	−0.005 (3)	−0.004 (3)	−0.002 (3)
C13	0.053 (4)	0.040 (3)	0.050 (3)	0.001 (3)	0.000 (3)	−0.002 (3)
C14	0.068 (4)	0.050 (3)	0.122 (6)	−0.032 (4)	0.002 (4)	−0.019 (4)
C15	0.059 (4)	0.050 (3)	0.058 (4)	−0.004 (3)	0.010 (3)	0.000 (3)
C16	0.067 (4)	0.082 (5)	0.073 (5)	0.036 (4)	0.004 (4)	−0.009 (4)
C17	0.063 (4)	0.102 (6)	0.081 (5)	0.018 (5)	0.001 (4)	0.017 (5)
C18	0.051 (4)	0.107 (6)	0.065 (5)	−0.003 (4)	0.010 (4)	−0.001 (5)
C19	0.084 (5)	0.082 (5)	0.069 (5)	−0.010 (5)	0.030 (4)	−0.017 (4)
C20	0.081 (5)	0.068 (4)	0.049 (4)	0.029 (4)	0.013 (4)	−0.005 (3)
C21	0.113 (7)	0.215 (10)	0.068 (5)	−0.005 (7)	−0.021 (5)	−0.025 (6)

Geometric parameters (Å, º) top

S—O4	1.417 (4)	C7—C8	1.380 (6)
S—O3	1.443 (3)	C7—C12	1.382 (7)
S—N	1.668 (4)	C8—C9	1.383 (6)
S—C15	1.745 (6)	C8—C13	1.500 (7)
Cl—C10	1.711 (5)	C9—C10	1.377 (6)
O1—C3	1.299 (7)	C9—H9A	0.9300
O1—C2	1.424 (9)	C10—C11	1.390 (7)
O2—C3	1.181 (7)	C11—C12	1.380 (7)
O5—C13	1.353 (5)	C11—H11A	0.9300
O5—C14	1.461 (6)	C12—H12A	0.9300
O6—C13	1.181 (6)	C14—H14A	0.9600
N—C7	1.437 (6)	C14—H14B	0.9600
N—C6	1.480 (5)	C14—H14C	0.9600
C1—C2	1.387 (10)	C15—C20	1.375 (7)
C1—H1A	0.9600	C15—C16	1.392 (7)
C1—H1B	0.9600	C16—C17	1.371 (8)
C1—H1C	0.9600	C16—H16A	0.9300
C2—H2A	0.9700	C17—C18	1.367 (8)
C2—H2B	0.9700	C17—H17A	0.9300
C3—C4	1.525 (8)	C18—C19	1.360 (8)
C4—C5	1.484 (7)	C18—C21	1.504 (8)
C4—H4B	0.9700	C19—C20	1.368 (8)
C4—H4C	0.9700	C19—H19A	0.9300
C5—C6	1.501 (7)	C20—H20A	0.9300
C5—H5A	0.9700	C21—H21A	0.9600
C5—H5B	0.9700	C21—H21B	0.9600
C6—H6A	0.9700	C21—H21C	0.9600
C6—H6B	0.9700

O4—S—O3	120.1 (2)	C7—C8—C13	123.0 (4)
O4—S—N	107.0 (2)	C9—C8—C13	117.3 (5)
O3—S—N	106.7 (2)	C10—C9—C8	122.0 (5)
O4—S—C15	108.5 (3)	C10—C9—H9A	119.0
O3—S—C15	107.6 (2)	C8—C9—H9A	119.0
N—S—C15	106.2 (2)	C9—C10—C11	118.6 (5)
C3—O1—C2	118.1 (7)	C9—C10—Cl	121.6 (4)
C13—O5—C14	114.1 (4)	C11—C10—Cl	119.7 (4)
C7—N—C6	118.5 (4)	C12—C11—C10	118.9 (5)
C7—N—S	114.7 (3)	C12—C11—H11A	120.5
C6—N—S	116.1 (3)	C10—C11—H11A	120.5
C2—C1—H1A	109.5	C11—C12—C7	122.6 (5)
C2—C1—H1B	109.5	C11—C12—H12A	118.7
H1A—C1—H1B	109.5	C7—C12—H12A	118.7
C2—C1—H1C	109.5	O6—C13—O5	124.5 (5)
H1A—C1—H1C	109.5	O6—C13—C8	126.0 (5)
H1B—C1—H1C	109.5	O5—C13—C8	109.5 (5)
C1—C2—O1	117.8 (9)	O5—C14—H14A	109.5
C1—C2—H2A	107.9	O5—C14—H14B	109.5
O1—C2—H2A	107.9	H14A—C14—H14B	109.5
C1—C2—H2B	107.9	O5—C14—H14C	109.5
O1—C2—H2B	107.9	H14A—C14—H14C	109.5
H2A—C2—H2B	107.2	H14B—C14—H14C	109.5
O2—C3—O1	122.2 (7)	C20—C15—C16	118.2 (6)
O2—C3—C4	127.4 (7)	C20—C15—S	121.4 (5)
O1—C3—C4	110.2 (6)	C16—C15—S	120.1 (5)
C5—C4—C3	111.5 (5)	C17—C16—C15	120.6 (6)
C5—C4—H4B	109.3	C17—C16—H16A	119.7
C3—C4—H4B	109.3	C15—C16—H16A	119.7
C5—C4—H4C	109.3	C18—C17—C16	119.8 (6)
C3—C4—H4C	109.3	C18—C17—H17A	120.1
H4B—C4—H4C	108.0	C16—C17—H17A	120.1
C4—C5—C6	113.4 (5)	C19—C18—C17	119.9 (7)
C4—C5—H5A	108.9	C19—C18—C21	121.1 (7)
C6—C5—H5A	108.9	C17—C18—C21	119.0 (7)
C4—C5—H5B	108.9	C18—C19—C20	120.8 (6)
C6—C5—H5B	108.9	C18—C19—H19A	119.6
H5A—C5—H5B	107.7	C20—C19—H19A	119.6
N—C6—C5	111.5 (4)	C19—C20—C15	120.5 (6)
N—C6—H6A	109.3	C19—C20—H20A	119.8
C5—C6—H6A	109.3	C15—C20—H20A	119.8
N—C6—H6B	109.3	C18—C21—H21A	109.5
C5—C6—H6B	109.3	C18—C21—H21B	109.5
H6A—C6—H6B	108.0	H21A—C21—H21B	109.5
C8—C7—C12	118.1 (5)	C18—C21—H21C	109.5
C8—C7—N	121.4 (4)	H21A—C21—H21C	109.5
C12—C7—N	120.4 (5)	H21B—C21—H21C	109.5
C7—C8—C9	119.7 (5)

O4—S—N—C7	173.3 (4)	C9—C10—C11—C12	−0.8 (8)
O3—S—N—C7	43.6 (4)	Cl—C10—C11—C12	179.9 (4)
C15—S—N—C7	−71.0 (4)	C10—C11—C12—C7	0.8 (9)
O4—S—N—C6	−42.5 (4)	C8—C7—C12—C11	0.5 (8)
O3—S—N—C6	−172.2 (4)	N—C7—C12—C11	176.5 (5)
C15—S—N—C6	73.2 (4)	C14—O5—C13—O6	2.0 (8)
C3—O1—C2—C1	−175.0 (9)	C14—O5—C13—C8	−177.4 (4)
C2—O1—C3—O2	−6.6 (12)	C7—C8—C13—O6	−47.9 (8)
C2—O1—C3—C4	177.6 (7)	C9—C8—C13—O6	130.6 (6)
O2—C3—C4—C5	−2.1 (10)	C7—C8—C13—O5	131.6 (5)
O1—C3—C4—C5	173.4 (6)	C9—C8—C13—O5	−49.9 (6)
C3—C4—C5—C6	−175.8 (5)	O4—S—C15—C20	28.1 (5)
C7—N—C6—C5	−69.4 (6)	O3—S—C15—C20	159.4 (4)
S—N—C6—C5	147.8 (4)	N—S—C15—C20	−86.6 (5)
C4—C5—C6—N	−65.9 (6)	O4—S—C15—C16	−157.0 (4)
C6—N—C7—C8	137.4 (5)	O3—S—C15—C16	−25.7 (5)
S—N—C7—C8	−79.3 (5)	N—S—C15—C16	88.2 (5)
C6—N—C7—C12	−38.6 (7)	C20—C15—C16—C17	−3.8 (9)
S—N—C7—C12	104.8 (5)	S—C15—C16—C17	−178.8 (5)
C12—C7—C8—C9	−1.6 (7)	C15—C16—C17—C18	4.0 (10)
N—C7—C8—C9	−177.7 (5)	C16—C17—C18—C19	−1.0 (10)
C12—C7—C8—C13	176.8 (5)	C16—C17—C18—C21	178.6 (6)
N—C7—C8—C13	0.8 (7)	C17—C18—C19—C20	−2.1 (10)
C7—C8—C9—C10	1.7 (8)	C21—C18—C19—C20	178.3 (6)
C13—C8—C9—C10	−176.9 (5)	C18—C19—C20—C15	2.2 (9)
C8—C9—C10—C11	−0.4 (8)	C16—C15—C20—C19	0.7 (8)
C8—C9—C10—Cl	178.9 (4)	S—C15—C20—C19	175.7 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6A···O4	0.97	2.41	2.903 (6)	111
C11—H11A···O3ⁱ	0.93	2.55	3.275 (6)	135
C14—H14A···O2ⁱⁱ	0.96	2.60	3.338 (7)	134
C17—H17A···O2ⁱⁱⁱ	0.93	2.59	3.414 (8)	148

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₄ClNO₆S
M_r	453.92
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	9.1480 (18), 10.742 (2), 23.258 (5)
V (Å³)	2285.5 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.29
Crystal size (mm)	0.30 × 0.10 × 0.05

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.917, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	4623, 4130, 2134
R_int	0.072
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.114, 0.92
No. of reflections	4130
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.21
Absolute structure	Flack (1983), 1748 Friedel pairs
Absolute structure parameter	0.03 (12)

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11A···O3ⁱ	0.9300	2.5500	3.275 (6)	135
C14—H14A···O2ⁱⁱ	0.9600	2.6000	3.338 (7)	134
C17—H17A···O2ⁱⁱⁱ	0.9300	2.5900	3.414 (8)	148

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

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Enraf–Nonius (1989). CAD-4 EXPRESS. Enraf–Nonius, Delft. The Netherlands. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Kondo, K., Ogawa, H., Yamashita, H. & Miyamoto, H. (1999). Bioorg. Med. Chem. 7, 1743–1754. Web of Science CrossRef PubMed CAS Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 66| Part 7| July 2010| Page o1819

doi:10.1107/S1600536810023792

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Methyl 5-chloro-2-[N-(3-eth­­oxy­carbonyl­prop­yl)-4-methyl­benzene­sulfonamido]­benzoate

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organic compounds

Methyl 5-chloro-2-[N-(3-ethoxycarbonylpropyl)-4-methylbenzenesulfonamido]benzoate