Methyl 5-chloro-2-[N-(3-eth-oxy-carbonyl-prop-yl)-4-methyl-benzene-sulfonamido]-benzoate.

In the title compound, C(21)H(24)ClNO(6)S, the benzene rings are oriented at a dihedral angles of 41.6 (2)°. In the crystal structure, weak inter-molecular C-H⋯O inter-actions link the mol-ecules.

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 = 453.92

Orthorhombic,

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[F 2 > 2σ(F 2)] = 0.063

wR(F 2) = 0.114

S = 0.92

4130 reflections

271 parameters

H-atom parameters constrained

Δρmax = 0.19 e Å−3

Δρmin = −0.21 e Å−3

Absolute structure: Flack (1983 ▶), 1748 Friedel pairs

Flack parameter: 0.03 (12)

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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H24ClNO6S	Dx = 1.319 Mg m−3
Mr = 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

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

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(Fo2) + (0.025P)2] where P = (Fo2 + 2Fc2)/3
S = 0.92	(Δ/σ)max < 0.001
4130 reflections	Δρmax = 0.19 e Å−3
271 parameters	Δρmin = −0.21 e Å−3
0 restraints	Absolute structure: Flack (1983), 1748 Friedel pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.03 (12)

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) ; (iii) .