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Acta Crystallogr Sect E Struct Rep Online. 2010 July 1; 66(Pt 7): o1819.
Published online 2010 June 26. doi:  10.1107/S1600536810023792
PMCID: PMC3006966

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

Abstract

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 [triangle]). For bond-length data, see: Allen et al. (1987 [triangle]).

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Object name is e-66-o1819-scheme1.jpg

Experimental

Crystal data

  • C21H24ClNO6S
  • M r = 453.92
  • Orthorhombic, An external file that holds a picture, illustration, etc.
Object name is e-66-o1819-efi1.jpg
  • 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 [triangle]) 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 [triangle]), 1748 Friedel pairs
  • Flack parameter: 0.03 (12)

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

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

supplementary crystallographic information

Comment

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.

Experimental

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.

Refinement

H atoms were positioned geometrically, with C-H =0.93, 0.98 and 0.96 Å for aromatic, methine and methyl H, respectively, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C,N), where x = 1.5 for methyl H and x = 1.2 for all other H atoms.

Figures

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

Crystal data

C21H24ClNO6SDx = 1.319 Mg m3
Mr = 453.92Melting point: 353 K
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 25 reflections
a = 9.1480 (18) Åθ = 8–12°
b = 10.742 (2) ŵ = 0.29 mm1
c = 23.258 (5) ÅT = 296 K
V = 2285.5 (8) Å3Needle, colorless
Z = 40.30 × 0.10 × 0.05 mm
F(000) = 952

Data collection

Enraf–Nonius CAD-4 diffractometer2134 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.072
graphiteθmax = 25.3°, θmin = 1.8°
ω/2θ scansh = −10→0
Absorption correction: ψ scan (North et al., 1968)k = −12→0
Tmin = 0.917, Tmax = 0.985l = −27→27
4623 measured reflections3 standard reflections every 200 reflections
4130 independent reflections intensity decay: 1%

Refinement

Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.063H-atom parameters constrained
wR(F2) = 0.114w = 1/[σ2(Fo2) + (0.025P)2] where P = (Fo2 + 2Fc2)/3
S = 0.92(Δ/σ)max < 0.001
4130 reflectionsΔρmax = 0.19 e Å3
271 parametersΔρmin = −0.21 e Å3
0 restraintsAbsolute structure: Flack (1983), 1748 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.03 (12)

Special details

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)

xyzUiso*/Ueq
S0.32206 (15)0.97963 (12)0.21916 (6)0.0523 (4)
Cl−0.34814 (14)1.01035 (14)0.35104 (7)0.0753 (5)
O10.5372 (6)0.6826 (5)0.4389 (3)0.130 (2)
O20.3409 (6)0.5726 (4)0.4257 (2)0.1119 (19)
O30.2927 (4)1.1049 (3)0.23835 (15)0.0605 (11)
O40.4681 (4)0.9398 (3)0.21051 (16)0.0668 (12)
O50.1790 (4)1.2067 (3)0.35132 (15)0.0537 (9)
O60.3165 (4)1.0402 (3)0.37290 (16)0.0651 (11)
N0.2482 (4)0.8844 (3)0.26778 (18)0.0459 (12)
C10.6798 (12)0.6647 (8)0.5254 (4)0.165 (4)
H1A0.68200.62040.56130.247*
H1B0.67140.75240.53280.247*
H1C0.76840.64870.50450.247*
C20.5609 (11)0.6252 (9)0.4933 (4)0.145 (4)
H2A0.47370.63720.51630.174*
H2B0.57130.53630.48690.174*
C30.4202 (8)0.6527 (6)0.4104 (3)0.077 (2)
C40.4113 (6)0.7278 (5)0.3548 (3)0.0671 (17)
H4B0.39820.81520.36410.080*
H4C0.50230.71930.33380.080*
C50.2883 (6)0.6854 (5)0.3181 (2)0.0570 (16)
H5A0.19710.69940.33840.068*
H5B0.29780.59660.31160.068*
C60.2816 (6)0.7504 (4)0.2610 (2)0.0553 (16)
H6A0.37460.74110.24150.066*
H6B0.20690.71180.23740.066*
C70.1045 (6)0.9196 (4)0.2868 (2)0.0452 (13)
C80.0844 (5)1.0121 (4)0.3272 (2)0.0412 (12)
C9−0.0552 (5)1.0403 (5)0.3460 (2)0.0543 (15)
H9A−0.06781.10430.37250.065*
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−0.23600.83610.27340.073*
C12−0.0171 (6)0.8557 (5)0.2676 (3)0.0562 (16)
H12A−0.00450.79270.24050.067*
C130.2085 (6)1.0834 (4)0.3535 (2)0.0476 (13)
C140.2962 (6)1.2856 (5)0.3736 (3)0.080 (2)
H14A0.26761.37140.37090.120*
H14B0.38341.27240.35140.120*
H14C0.31471.26480.41310.120*
C150.2247 (6)0.9560 (5)0.1556 (2)0.0558 (15)
C160.0987 (6)1.0246 (6)0.1445 (3)0.0737 (18)
H16A0.06771.08420.17080.088*
C170.0199 (7)1.0052 (7)0.0952 (3)0.082 (2)
H17A−0.06071.05490.08700.098*
C180.0601 (7)0.9126 (7)0.0581 (3)0.074 (2)
C190.1794 (8)0.8414 (6)0.0698 (3)0.078 (2)
H19A0.20450.77680.04510.094*
C200.2628 (7)0.8637 (6)0.1175 (2)0.0659 (18)
H20A0.34600.81600.12420.079*
C21−0.0298 (8)0.8910 (8)0.0048 (3)0.132 (3)
H21A−0.10740.95110.00320.198*
H21B−0.07050.80870.00590.198*
H21C0.03110.8995−0.02850.198*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S0.0493 (8)0.0417 (7)0.0659 (10)−0.0006 (8)0.0099 (8)0.0019 (8)
Cl0.0481 (8)0.0653 (10)0.1124 (13)−0.0118 (8)0.0152 (9)−0.0006 (10)
O10.139 (5)0.116 (4)0.134 (5)−0.032 (4)−0.076 (4)0.041 (4)
O20.134 (5)0.089 (4)0.113 (4)−0.045 (4)−0.014 (4)0.026 (3)
O30.084 (3)0.0296 (18)0.068 (3)0.002 (2)0.012 (2)−0.0045 (17)
O40.054 (2)0.063 (3)0.083 (3)−0.006 (2)0.017 (2)−0.006 (2)
O50.046 (2)0.0352 (18)0.080 (3)−0.0061 (18)−0.001 (2)−0.0094 (19)
O60.056 (2)0.051 (2)0.088 (3)0.009 (2)−0.016 (2)−0.007 (2)
N0.055 (3)0.031 (2)0.051 (3)0.000 (2)0.014 (2)0.001 (2)
C10.192 (12)0.155 (9)0.148 (9)−0.042 (9)−0.011 (9)−0.002 (7)
C20.163 (10)0.136 (8)0.138 (9)−0.013 (8)−0.045 (8)0.033 (7)
C30.087 (6)0.056 (4)0.087 (5)−0.010 (4)−0.028 (5)−0.004 (4)
C40.070 (4)0.041 (3)0.090 (5)0.008 (3)−0.011 (4)0.007 (4)
C50.057 (4)0.039 (3)0.075 (4)0.002 (3)−0.005 (3)0.004 (3)
C60.068 (4)0.029 (3)0.070 (4)0.013 (3)0.007 (3)−0.001 (3)
C70.046 (3)0.033 (3)0.056 (4)0.000 (3)0.005 (3)0.007 (3)
C80.034 (3)0.030 (3)0.060 (3)−0.008 (3)0.003 (2)0.004 (3)
C90.046 (3)0.040 (3)0.077 (4)−0.004 (3)−0.006 (3)0.006 (3)
C100.050 (3)0.039 (3)0.076 (4)−0.007 (3)0.002 (3)0.003 (3)
C110.052 (4)0.051 (3)0.080 (4)0.000 (3)−0.011 (4)0.003 (3)
C120.057 (4)0.039 (3)0.072 (5)−0.005 (3)−0.004 (3)−0.002 (3)
C130.053 (4)0.040 (3)0.050 (3)0.001 (3)0.000 (3)−0.002 (3)
C140.068 (4)0.050 (3)0.122 (6)−0.032 (4)0.002 (4)−0.019 (4)
C150.059 (4)0.050 (3)0.058 (4)−0.004 (3)0.010 (3)0.000 (3)
C160.067 (4)0.082 (5)0.073 (5)0.036 (4)0.004 (4)−0.009 (4)
C170.063 (4)0.102 (6)0.081 (5)0.018 (5)0.001 (4)0.017 (5)
C180.051 (4)0.107 (6)0.065 (5)−0.003 (4)0.010 (4)−0.001 (5)
C190.084 (5)0.082 (5)0.069 (5)−0.010 (5)0.030 (4)−0.017 (4)
C200.081 (5)0.068 (4)0.049 (4)0.029 (4)0.013 (4)−0.005 (3)
C210.113 (7)0.215 (10)0.068 (5)−0.005 (7)−0.021 (5)−0.025 (6)

Geometric parameters (Å, °)

S—O41.417 (4)C7—C81.380 (6)
S—O31.443 (3)C7—C121.382 (7)
S—N1.668 (4)C8—C91.383 (6)
S—C151.745 (6)C8—C131.500 (7)
Cl—C101.711 (5)C9—C101.377 (6)
O1—C31.299 (7)C9—H9A0.9300
O1—C21.424 (9)C10—C111.390 (7)
O2—C31.181 (7)C11—C121.380 (7)
O5—C131.353 (5)C11—H11A0.9300
O5—C141.461 (6)C12—H12A0.9300
O6—C131.181 (6)C14—H14A0.9600
N—C71.437 (6)C14—H14B0.9600
N—C61.480 (5)C14—H14C0.9600
C1—C21.387 (10)C15—C201.375 (7)
C1—H1A0.9600C15—C161.392 (7)
C1—H1B0.9600C16—C171.371 (8)
C1—H1C0.9600C16—H16A0.9300
C2—H2A0.9700C17—C181.367 (8)
C2—H2B0.9700C17—H17A0.9300
C3—C41.525 (8)C18—C191.360 (8)
C4—C51.484 (7)C18—C211.504 (8)
C4—H4B0.9700C19—C201.368 (8)
C4—H4C0.9700C19—H19A0.9300
C5—C61.501 (7)C20—H20A0.9300
C5—H5A0.9700C21—H21A0.9600
C5—H5B0.9700C21—H21B0.9600
C6—H6A0.9700C21—H21C0.9600
C6—H6B0.9700
O4—S—O3120.1 (2)C7—C8—C13123.0 (4)
O4—S—N107.0 (2)C9—C8—C13117.3 (5)
O3—S—N106.7 (2)C10—C9—C8122.0 (5)
O4—S—C15108.5 (3)C10—C9—H9A119.0
O3—S—C15107.6 (2)C8—C9—H9A119.0
N—S—C15106.2 (2)C9—C10—C11118.6 (5)
C3—O1—C2118.1 (7)C9—C10—Cl121.6 (4)
C13—O5—C14114.1 (4)C11—C10—Cl119.7 (4)
C7—N—C6118.5 (4)C12—C11—C10118.9 (5)
C7—N—S114.7 (3)C12—C11—H11A120.5
C6—N—S116.1 (3)C10—C11—H11A120.5
C2—C1—H1A109.5C11—C12—C7122.6 (5)
C2—C1—H1B109.5C11—C12—H12A118.7
H1A—C1—H1B109.5C7—C12—H12A118.7
C2—C1—H1C109.5O6—C13—O5124.5 (5)
H1A—C1—H1C109.5O6—C13—C8126.0 (5)
H1B—C1—H1C109.5O5—C13—C8109.5 (5)
C1—C2—O1117.8 (9)O5—C14—H14A109.5
C1—C2—H2A107.9O5—C14—H14B109.5
O1—C2—H2A107.9H14A—C14—H14B109.5
C1—C2—H2B107.9O5—C14—H14C109.5
O1—C2—H2B107.9H14A—C14—H14C109.5
H2A—C2—H2B107.2H14B—C14—H14C109.5
O2—C3—O1122.2 (7)C20—C15—C16118.2 (6)
O2—C3—C4127.4 (7)C20—C15—S121.4 (5)
O1—C3—C4110.2 (6)C16—C15—S120.1 (5)
C5—C4—C3111.5 (5)C17—C16—C15120.6 (6)
C5—C4—H4B109.3C17—C16—H16A119.7
C3—C4—H4B109.3C15—C16—H16A119.7
C5—C4—H4C109.3C18—C17—C16119.8 (6)
C3—C4—H4C109.3C18—C17—H17A120.1
H4B—C4—H4C108.0C16—C17—H17A120.1
C4—C5—C6113.4 (5)C19—C18—C17119.9 (7)
C4—C5—H5A108.9C19—C18—C21121.1 (7)
C6—C5—H5A108.9C17—C18—C21119.0 (7)
C4—C5—H5B108.9C18—C19—C20120.8 (6)
C6—C5—H5B108.9C18—C19—H19A119.6
H5A—C5—H5B107.7C20—C19—H19A119.6
N—C6—C5111.5 (4)C19—C20—C15120.5 (6)
N—C6—H6A109.3C19—C20—H20A119.8
C5—C6—H6A109.3C15—C20—H20A119.8
N—C6—H6B109.3C18—C21—H21A109.5
C5—C6—H6B109.3C18—C21—H21B109.5
H6A—C6—H6B108.0H21A—C21—H21B109.5
C8—C7—C12118.1 (5)C18—C21—H21C109.5
C8—C7—N121.4 (4)H21A—C21—H21C109.5
C12—C7—N120.4 (5)H21B—C21—H21C109.5
C7—C8—C9119.7 (5)
O4—S—N—C7173.3 (4)C9—C10—C11—C12−0.8 (8)
O3—S—N—C743.6 (4)Cl—C10—C11—C12179.9 (4)
C15—S—N—C7−71.0 (4)C10—C11—C12—C70.8 (9)
O4—S—N—C6−42.5 (4)C8—C7—C12—C110.5 (8)
O3—S—N—C6−172.2 (4)N—C7—C12—C11176.5 (5)
C15—S—N—C673.2 (4)C14—O5—C13—O62.0 (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—C4177.6 (7)C9—C8—C13—O6130.6 (6)
O2—C3—C4—C5−2.1 (10)C7—C8—C13—O5131.6 (5)
O1—C3—C4—C5173.4 (6)C9—C8—C13—O5−49.9 (6)
C3—C4—C5—C6−175.8 (5)O4—S—C15—C2028.1 (5)
C7—N—C6—C5−69.4 (6)O3—S—C15—C20159.4 (4)
S—N—C6—C5147.8 (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—C8137.4 (5)O3—S—C15—C16−25.7 (5)
S—N—C7—C8−79.3 (5)N—S—C15—C1688.2 (5)
C6—N—C7—C12−38.6 (7)C20—C15—C16—C17−3.8 (9)
S—N—C7—C12104.8 (5)S—C15—C16—C17−178.8 (5)
C12—C7—C8—C9−1.6 (7)C15—C16—C17—C184.0 (10)
N—C7—C8—C9−177.7 (5)C16—C17—C18—C19−1.0 (10)
C12—C7—C8—C13176.8 (5)C16—C17—C18—C21178.6 (6)
N—C7—C8—C130.8 (7)C17—C18—C19—C20−2.1 (10)
C7—C8—C9—C101.7 (8)C21—C18—C19—C20178.3 (6)
C13—C8—C9—C10−176.9 (5)C18—C19—C20—C152.2 (9)
C8—C9—C10—C11−0.4 (8)C16—C15—C20—C190.7 (8)
C8—C9—C10—Cl178.9 (4)S—C15—C20—C19175.7 (5)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C6—H6A···O40.972.412.903 (6)111
C11—H11A···O3i0.932.553.275 (6)135
C14—H14A···O2ii0.962.603.338 (7)134
C17—H17A···O2iii0.932.593.414 (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.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BQ2221).

References

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  • Kondo, K., Ogawa, H., Yamashita, H. & Miyamoto, H. (1999). Bioorg. Med. Chem.7, 1743–1754. [PubMed]
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