Literature DB >> 21583912

N-(5-Bromo-2-chloro-benz-yl)-N-cyclo-propyl-naphthalene-2-sulfonamide.

C Suneel Manohar Babu, Helen P Kavitha, R Arulmozhi, Jasmine P Vennila, V Manivannan.   

Abstract

In the title compound, C(20)H(17)BrClNO(2)S, the dihedral angle between the benzene ring and the naphthalene plane is 8.95 (8)°. The crystal packing is stabilized by weak inter-molecular C-H⋯O, C-H⋯Cl and π-π [centroid-centroid distance = 3.8782 (16) Å] inter-actions.

Entities:  

Year:  2009        PMID： 21583912      PMCID： PMC2977776          DOI： 10.1107/S1600536809014457

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For biological activity, see: Li et al. (1995 ▶); Maren (1976 ▶); Misra et al. (1982 ▶); Yoshino et al. (1992 ▶). For related structures, see: Ramachandran et al. (2008 ▶); Vennila et al. (2009 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C20H17BrClNO2S M = 450.77 Monoclinic, a = 12.1759 (5) Å b = 7.5881 (3) Å c = 20.5752 (8) Å β = 95.393 (1)° V = 1892.57 (13) Å3 Z = 4 Mo Kα radiation μ = 2.44 mm−1 T = 295 K 0.22 × 0.18 × 0.14 mm

Data collection

Bruker KappaAPEXII diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.616, T max = 0.727 23845 measured reflections 5240 independent reflections 3528 reflections with I > 2σ(I) R int = 0.029

Refinement

R[F 2 > 2σ(F 2)] = 0.039 wR(F 2) = 0.103 S = 1.01 5240 reflections 235 parameters H-atom parameters constrained Δρmax = 0.71 e Å−3 Δρmin = −0.81 e Å−3 Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809014457/gk2206sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809014457/gk2206Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C20H17BrClNO2SF(000) = 912
Mr = 450.77Dx = 1.582 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 6275 reflections
a = 12.1759 (5) Åθ = 2.5–29.7°
b = 7.5881 (3) ŵ = 2.44 mm−1
c = 20.5752 (8) ÅT = 295 K
β = 95.393 (1)°Block, colourless
V = 1892.57 (13) Å30.22 × 0.18 × 0.14 mm
Z = 4
Bruker KappaAPEXII diffractometer5240 independent reflections
Radiation source: fine-focus sealed tube3528 reflections with I > 2σ(I)
graphiteRint = 0.029
ω and φ scansθmax = 29.7°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −16→16
Tmin = 0.616, Tmax = 0.727k = −9→10
23845 measured reflectionsl = −28→26
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103H-atom parameters constrained
S = 1.01w = 1/[σ2(Fo2) + (0.0433P)2 + 1.1018P] where P = (Fo2 + 2Fc2)/3
5240 reflections(Δ/σ)max < 0.001
235 parametersΔρmax = 0.71 e Å−3
0 restraintsΔρmin = −0.81 e Å−3
xyzUiso*/Ueq
Br10.04003 (2)0.91779 (4)0.097687 (17)0.06646 (13)
Cl1−0.44538 (6)0.63579 (10)0.11975 (3)0.05481 (18)
S1−0.36612 (5)0.92504 (8)−0.10261 (2)0.03567 (13)
N1−0.31258 (15)0.7424 (3)−0.07080 (8)0.0388 (4)
O1−0.30118 (14)0.9756 (3)−0.15345 (8)0.0490 (4)
O2−0.37562 (15)1.0407 (3)−0.04900 (8)0.0528 (5)
C1−0.27720 (18)0.7338 (3)0.05050 (10)0.0360 (5)
C2−0.17142 (18)0.7960 (3)0.04688 (11)0.0411 (5)
H2−0.14490.81250.00640.049*
C3−0.1051 (2)0.8337 (4)0.10303 (13)0.0465 (6)
C4−0.1415 (2)0.8122 (4)0.16319 (13)0.0607 (8)
H4−0.09570.83880.20060.073*
C5−0.2464 (2)0.7508 (4)0.16785 (12)0.0583 (7)
H5−0.27220.73500.20860.070*
C6−0.31283 (19)0.7129 (3)0.11212 (11)0.0405 (5)
C7−0.3536 (2)0.6863 (4)−0.00886 (11)0.0484 (6)
H7A−0.36420.5596−0.00980.058*
H7B−0.42490.7406−0.00520.058*
C8−0.2972 (2)0.6020 (3)−0.11672 (13)0.0488 (6)
H8−0.36420.5537−0.14020.059*
C9−0.1969 (3)0.6016 (5)−0.15207 (18)0.0736 (10)
H9A−0.20330.5561−0.19630.088*
H9B−0.14540.6984−0.14410.088*
C10−0.2075 (3)0.4754 (5)−0.0985 (2)0.0897 (12)
H10A−0.16250.4949−0.05770.108*
H10B−0.22030.3526−0.10990.108*
C11−0.49910 (18)0.8701 (3)−0.13796 (10)0.0345 (5)
C20−0.5150 (2)0.8332 (4)−0.20527 (10)0.0441 (6)
H20−0.45730.8467−0.23140.053*
C19−0.6153 (2)0.7776 (4)−0.23142 (11)0.0472 (6)
H19−0.62630.7558−0.27600.057*
C18−0.70337 (19)0.7521 (3)−0.19266 (11)0.0421 (5)
C13−0.68651 (18)0.7903 (3)−0.12488 (11)0.0365 (5)
C12−0.58277 (18)0.8532 (3)−0.09876 (10)0.0352 (5)
H12−0.57140.8832−0.05480.042*
C17−0.8073 (2)0.6872 (4)−0.21798 (14)0.0573 (7)
H17−0.82050.6641−0.26240.069*
C16−0.8879 (2)0.6582 (4)−0.17825 (16)0.0655 (8)
H16−0.95580.6147−0.19570.079*
C15−0.8704 (2)0.6928 (4)−0.11131 (15)0.0590 (7)
H15−0.92630.6700−0.08460.071*
C14−0.7729 (2)0.7593 (4)−0.08508 (13)0.0476 (6)
H14−0.76280.7846−0.04070.057*
U11U22U33U12U13U23
Br10.03377 (15)0.0702 (2)0.0924 (2)−0.00308 (13)−0.00958 (14)0.00913 (17)
Cl10.0471 (4)0.0642 (4)0.0555 (3)−0.0071 (3)0.0171 (3)0.0071 (3)
S10.0333 (3)0.0404 (3)0.0328 (2)−0.0043 (2)0.0008 (2)0.0009 (2)
N10.0352 (10)0.0467 (12)0.0339 (8)−0.0017 (9)0.0002 (7)0.0075 (8)
O10.0417 (9)0.0582 (12)0.0474 (9)−0.0087 (8)0.0056 (7)0.0160 (8)
O20.0506 (11)0.0555 (12)0.0511 (9)−0.0067 (9)−0.0021 (8)−0.0184 (8)
C10.0338 (11)0.0356 (13)0.0379 (10)0.0029 (9)0.0001 (8)0.0086 (9)
C20.0325 (11)0.0468 (15)0.0434 (11)0.0000 (10)0.0009 (9)0.0110 (10)
C30.0341 (12)0.0456 (15)0.0578 (14)0.0034 (11)−0.0066 (10)0.0072 (12)
C40.0596 (17)0.074 (2)0.0452 (13)−0.0058 (15)−0.0117 (12)0.0014 (14)
C50.0649 (18)0.073 (2)0.0376 (12)−0.0087 (16)0.0059 (12)0.0004 (13)
C60.0394 (12)0.0396 (14)0.0432 (11)0.0007 (10)0.0065 (9)0.0068 (10)
C70.0396 (13)0.0652 (18)0.0394 (11)−0.0108 (12)−0.0004 (10)0.0158 (12)
C80.0416 (14)0.0456 (16)0.0587 (14)0.0003 (11)0.0016 (11)0.0001 (12)
C90.0554 (19)0.076 (2)0.093 (2)0.0054 (16)0.0246 (17)−0.0170 (19)
C100.090 (3)0.073 (3)0.103 (3)0.033 (2)−0.004 (2)−0.003 (2)
C110.0329 (11)0.0381 (13)0.0317 (9)0.0020 (9)−0.0007 (8)−0.0017 (9)
C200.0456 (13)0.0547 (16)0.0322 (10)−0.0004 (12)0.0045 (9)−0.0022 (10)
C190.0485 (14)0.0599 (17)0.0317 (10)0.0022 (12)−0.0042 (10)−0.0084 (11)
C180.0380 (12)0.0424 (14)0.0439 (12)0.0037 (10)−0.0070 (10)−0.0073 (10)
C130.0316 (11)0.0343 (13)0.0432 (11)0.0044 (9)0.0018 (9)−0.0033 (10)
C120.0339 (11)0.0393 (13)0.0320 (9)0.0051 (10)0.0008 (8)−0.0054 (9)
C170.0422 (14)0.0650 (19)0.0612 (15)0.0001 (13)−0.0141 (12)−0.0118 (14)
C160.0355 (14)0.070 (2)0.087 (2)−0.0029 (14)−0.0123 (14)−0.0122 (17)
C150.0324 (13)0.063 (2)0.082 (2)0.0015 (13)0.0083 (13)0.0011 (15)
C140.0373 (13)0.0525 (16)0.0534 (13)0.0046 (12)0.0059 (10)−0.0023 (12)
Br1—C31.891 (3)C9—C101.475 (5)
Cl1—C61.738 (2)C9—H9A0.9700
S1—O11.4220 (16)C9—H9B0.9700
S1—O21.4229 (17)C10—H10A0.9700
S1—N11.641 (2)C10—H10B0.9700
S1—C111.761 (2)C11—C121.363 (3)
N1—C81.448 (3)C11—C201.409 (3)
N1—C71.475 (3)C20—C191.356 (3)
C1—C21.380 (3)C20—H200.9300
C1—C61.387 (3)C19—C181.408 (3)
C1—C71.508 (3)C19—H190.9300
C2—C31.376 (3)C18—C171.411 (3)
C2—H20.9300C18—C131.420 (3)
C3—C41.363 (4)C13—C121.409 (3)
C4—C51.371 (4)C13—C141.412 (3)
C4—H40.9300C12—H120.9300
C5—C61.370 (4)C17—C161.353 (4)
C5—H50.9300C17—H170.9300
C7—H7A0.9700C16—C151.399 (4)
C7—H7B0.9700C16—H160.9300
C8—C101.475 (4)C15—C141.355 (4)
C8—C91.478 (4)C15—H150.9300
C8—H80.9800C14—H140.9300
O1—S1—O2119.67 (12)C8—C9—H9A117.8
O1—S1—N1107.09 (10)C10—C9—H9B117.8
O2—S1—N1105.66 (11)C8—C9—H9B117.8
O1—S1—C11108.25 (10)H9A—C9—H9B114.9
O2—S1—C11109.11 (11)C9—C10—C860.1 (2)
N1—S1—C11106.27 (11)C9—C10—H10A117.8
C8—N1—C7115.3 (2)C8—C10—H10A117.8
C8—N1—S1115.61 (15)C9—C10—H10B117.8
C7—N1—S1115.72 (17)C8—C10—H10B117.8
C2—C1—C6117.5 (2)H10A—C10—H10B114.9
C2—C1—C7123.1 (2)C12—C11—C20121.5 (2)
C6—C1—C7119.4 (2)C12—C11—S1119.14 (15)
C3—C2—C1120.2 (2)C20—C11—S1119.26 (17)
C3—C2—H2119.9C19—C20—C11119.2 (2)
C1—C2—H2119.9C19—C20—H20120.4
C4—C3—C2121.5 (2)C11—C20—H20120.4
C4—C3—Br1118.6 (2)C20—C19—C18121.6 (2)
C2—C3—Br1119.94 (19)C20—C19—H19119.2
C3—C4—C5119.3 (2)C18—C19—H19119.2
C3—C4—H4120.4C19—C18—C17122.9 (2)
C5—C4—H4120.4C19—C18—C13118.7 (2)
C6—C5—C4119.6 (2)C17—C18—C13118.4 (2)
C6—C5—H5120.2C12—C13—C14121.7 (2)
C4—C5—H5120.2C12—C13—C18119.0 (2)
C5—C6—C1122.0 (2)C14—C13—C18119.3 (2)
C5—C6—Cl1118.39 (19)C11—C12—C13119.95 (19)
C1—C6—Cl1119.60 (18)C11—C12—H12120.0
N1—C7—C1113.43 (19)C13—C12—H12120.0
N1—C7—H7A108.9C16—C17—C18120.7 (3)
C1—C7—H7A108.9C16—C17—H17119.7
N1—C7—H7B108.9C18—C17—H17119.7
C1—C7—H7B108.9C17—C16—C15120.9 (3)
H7A—C7—H7B107.7C17—C16—H16119.6
N1—C8—C10116.8 (3)C15—C16—H16119.6
N1—C8—C9119.1 (2)C14—C15—C16120.6 (3)
C10—C8—C959.9 (2)C14—C15—H15119.7
N1—C8—H8116.4C16—C15—H15119.7
C10—C8—H8116.4C15—C14—C13120.2 (2)
C9—C8—H8116.4C15—C14—H14119.9
C10—C9—C859.9 (2)C13—C14—H14119.9
C10—C9—H9A117.8
O1—S1—N1—C8−52.60 (19)N1—C8—C10—C9−109.7 (3)
O2—S1—N1—C8178.78 (17)O1—S1—C11—C12−166.32 (19)
C11—S1—N1—C862.93 (19)O2—S1—C11—C12−34.6 (2)
O1—S1—N1—C7168.24 (16)N1—S1—C11—C1278.9 (2)
O2—S1—N1—C739.62 (19)O1—S1—C11—C2017.9 (2)
C11—S1—N1—C7−76.22 (18)O2—S1—C11—C20149.7 (2)
C6—C1—C2—C30.4 (4)N1—S1—C11—C20−96.8 (2)
C7—C1—C2—C3−178.7 (2)C12—C11—C20—C19−0.8 (4)
C1—C2—C3—C4−0.4 (4)S1—C11—C20—C19174.9 (2)
C1—C2—C3—Br1179.70 (19)C11—C20—C19—C18−1.5 (4)
C2—C3—C4—C50.3 (5)C20—C19—C18—C17−177.2 (3)
Br1—C3—C4—C5−179.8 (2)C20—C19—C18—C131.6 (4)
C3—C4—C5—C6−0.3 (5)C19—C18—C13—C120.4 (4)
C4—C5—C6—C10.3 (5)C17—C18—C13—C12179.3 (2)
C4—C5—C6—Cl1−179.9 (2)C19—C18—C13—C14−177.7 (2)
C2—C1—C6—C5−0.4 (4)C17—C18—C13—C141.1 (4)
C7—C1—C6—C5178.8 (3)C20—C11—C12—C132.8 (4)
C2—C1—C6—Cl1179.79 (19)S1—C11—C12—C13−172.87 (18)
C7—C1—C6—Cl1−1.0 (3)C14—C13—C12—C11175.5 (2)
C8—N1—C7—C1120.9 (2)C18—C13—C12—C11−2.6 (3)
S1—N1—C7—C1−99.8 (2)C19—C18—C17—C16177.3 (3)
C2—C1—C7—N1−10.4 (4)C13—C18—C17—C16−1.5 (4)
C6—C1—C7—N1170.4 (2)C18—C17—C16—C150.4 (5)
C7—N1—C8—C10−68.4 (3)C17—C16—C15—C141.2 (5)
S1—N1—C8—C10152.3 (2)C16—C15—C14—C13−1.6 (4)
C7—N1—C8—C9−137.2 (3)C12—C13—C14—C15−177.7 (3)
S1—N1—C8—C983.5 (3)C18—C13—C14—C150.4 (4)
N1—C8—C9—C10105.9 (3)
D—H···AD—HH···AD···AD—H···A
C2—H2···N10.932.522.864 (3)102
C20—H20···O10.932.562.926 (3)104
C8—H8···Cl1i0.982.793.612 (3)142
C12—H12···O2ii0.932.363.231 (3)156
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C8—H8⋯Cl1i0.982.793.612 (3)142
C12—H12⋯O2ii0.932.363.231 (3)156

Symmetry codes: (i) ; (ii) .

  7 in total

1.  Novel sulfonamides as potential, systemically active antitumor agents.

Authors:  H Yoshino; N Ueda; J Niijima; H Sugumi; Y Kotake; N Koyanagi; K Yoshimatsu; M Asada; T Watanabe; T Nagasu
Journal:  J Med Chem       Date:  1992-06-26       Impact factor: 7.446

2.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

Review 3.  Relatons between structure and biological activity of sulfonamides.

Authors:  T H Maren
Journal:  Annu Rev Pharmacol Toxicol       Date:  1976       Impact factor: 13.820

4.  1,2-Diarylcyclopentenes as selective cyclooxygenase-2 inhibitors and orally active anti-inflammatory agents.

Authors:  J J Li; G D Anderson; E G Burton; J N Cogburn; J T Collins; D J Garland; S A Gregory; H C Huang; P C Isakson; C M Koboldt
Journal:  J Med Chem       Date:  1995-10-27       Impact factor: 7.446

5.  3-Amino-phenyl naphthalene-1-sulfonate.

Authors:  Jasmine P Vennila; Helen P Kavitha; D John Thiruvadigal; B R Venkatraman; V Manivannan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-12-10

6.  2,4-Dinitro-1-naphthyl 4-toluene-sulfonate.

Authors:  G Ramachandran; Charles Christopher Kanakam; V Manivannan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2008-04-18

7.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  7 in total
  1 in total

1.  4-Bromo-3-{N-[2-(3,4-dimethoxy-phen-yl)eth-yl]-N-methyl-sulfamo-yl}-5-methyl-benzoic acid monohydrate.

Authors:  C Suneel Manohar Babu; Helen P Kavitha; Jasmine P Vennila; G Chakkaravarthi; V Manivannan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-06-13
  1 in total

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