Literature DB >> 22199963

N-(Phenyl-sulfon-yl)naphtho-[2,1-b]furan-1-carboxamide.

M Shetprakash, P A Suchetan, B S Palakshamurthy, K M Mahadevan, V P Vaidya.   

Abstract

In the title compound, C(19)H(13)NO(4)S, the mol-ecule is twisted at the S atom with a C-S-N-C torsion angle of -65.2 (2)° between the benzene ring and the -SO(2)-NH-C=O segment. The dihedral angle between the benzene and the naphtho-furan ring system is 83.3 (1)°. In the crystal, mol-ecules are linked by N-H⋯O hydrogen bonds into chains running along the c axis. An intra-molecular N-H⋯O(furan) inter-action is also observed.

Entities:  

Year:  2011        PMID： 22199963      PMCID： PMC3239115          DOI： 10.1107/S1600536811050495

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


Related literature

For related structures, see: Gowda et al. (2009 ▶, 2010 ▶).

Experimental

Crystal data

C19H13NO4S M = 351.36 Monoclinic, a = 13.8504 (10) Å b = 12.2166 (8) Å c = 9.7164 (6) Å β = 101.248 (2)° V = 1612.48 (19) Å3 Z = 4 Mo Kα radiation μ = 0.23 mm−1 T = 299 K 0.35 × 0.3 × 0.25 mm

Data collection

Bruker APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.924, T max = 0.945 15289 measured reflections 2986 independent reflections 2394 reflections with I > 2σ(I) R int = 0.027

Refinement

R[F 2 > 2σ(F 2)] = 0.041 wR(F 2) = 0.133 S = 0.85 2986 reflections 231 parameters 1 restraint H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.25 e Å−3 Δρmin = −0.38 e Å−3 Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: APEX2 and SAINT-Plus (Bruker, 2004 ▶); data reduction: SAINT-Plus and XPREP (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: SHELXL97. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811050495/ds2146sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811050495/ds2146Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811050495/ds2146Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C19H13NO4SF(000) = 728
Mr = 351.361.447 Mg m-3
Monoclinic, P21/cDx = 1.447 Mg m−3
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71073 Å
a = 13.8504 (10) ÅCell parameters from 2986 reflections
b = 12.2166 (8) Åθ = 2.2°
c = 9.7164 (6) ŵ = 0.23 mm−1
β = 101.248 (2)°T = 299 K
V = 1612.48 (19) Å3Prism, colourless
Z = 40.35 × 0.3 × 0.25 mm
Bruker APEXII CCD area-detector diffractometer2986 independent reflections
Radiation source: fine-focus sealed tube2394 reflections with I > 2σ(I)
graphiteRint = 0.027
phi and scansθmax = 25.5°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −16→16
Tmin = 0.924, Tmax = 0.945k = −14→14
15289 measured reflectionsl = −11→11
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.041H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.133w = 1/[σ2(Fo2) + (0.0827P)2 + 1.1854P] where P = (Fo2 + 2Fc2)/3
S = 0.85(Δ/σ)max = 0.001
2986 reflectionsΔρmax = 0.25 e Å−3
231 parametersΔρmin = −0.38 e Å−3
1 restraintExtinction correction: SHELXL
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0054 (12)
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.
xyzUiso*/Ueq
H1N0.8221 (19)0.1816 (19)0.346 (3)0.053 (8)*
S10.72588 (4)0.25754 (5)0.18450 (6)0.0566 (2)
N10.82025 (14)0.24177 (18)0.3158 (2)0.0527 (5)
O10.69636 (15)0.14945 (17)0.1467 (2)0.0910 (7)
O20.75502 (14)0.3299 (2)0.08507 (18)0.0853 (7)
O30.85990 (12)0.42070 (13)0.35980 (18)0.0626 (5)
O40.96215 (10)0.17651 (11)0.52390 (14)0.0448 (4)
C11.14610 (14)0.26862 (18)0.8155 (2)0.0430 (5)
C21.18623 (16)0.3662 (2)0.8774 (2)0.0545 (6)
H21.16440.43320.83760.065*
C31.25770 (18)0.3628 (3)0.9968 (2)0.0663 (7)
H31.28410.42781.03770.08*
C41.29114 (18)0.2631 (3)1.0575 (3)0.0703 (8)
H41.33950.26211.13870.084*
C51.25403 (17)0.1678 (3)0.9995 (2)0.0636 (7)
H51.27710.1021.04160.076*
C61.18038 (15)0.16646 (19)0.8755 (2)0.0488 (5)
C71.14042 (17)0.0666 (2)0.8153 (2)0.0566 (6)
H71.16440.00110.85730.068*
C81.06823 (17)0.06330 (19)0.6984 (2)0.0550 (6)
H81.0426−0.00250.65930.066*
C91.03480 (14)0.16388 (17)0.6404 (2)0.0425 (5)
C101.06976 (14)0.26419 (16)0.6922 (2)0.0395 (4)
C111.01546 (14)0.34374 (17)0.6020 (2)0.0412 (4)
H111.02250.41940.6090.049*
C120.95188 (13)0.28806 (17)0.5044 (2)0.0404 (4)
C130.87507 (14)0.32539 (18)0.3889 (2)0.0430 (5)
C140.63289 (15)0.3220 (2)0.2518 (2)0.0502 (5)
C160.4993 (2)0.3091 (5)0.3712 (4)0.1040 (13)
H160.46010.26730.41860.125*
C150.57551 (19)0.2612 (3)0.3241 (3)0.0725 (8)
H150.58880.18720.34090.087*
C190.6169 (2)0.4313 (3)0.2335 (4)0.0876 (9)
H190.65670.47410.18820.105*
C170.4807 (3)0.4141 (5)0.3499 (5)0.1213 (18)
H170.42710.4450.38010.146*
C180.5377 (3)0.4776 (4)0.2854 (5)0.1210 (15)
H180.52490.55220.2750.145*
U11U22U33U12U13U23
S10.0409 (3)0.0788 (5)0.0460 (3)0.0105 (3)−0.0012 (2)−0.0159 (3)
N10.0427 (10)0.0551 (13)0.0552 (11)0.0046 (8)−0.0028 (8)−0.0053 (9)
O10.0699 (12)0.0851 (14)0.1006 (15)0.0202 (10)−0.0264 (11)−0.0464 (12)
O20.0582 (10)0.154 (2)0.0440 (9)0.0078 (12)0.0119 (8)0.0091 (11)
O30.0571 (9)0.0564 (10)0.0672 (10)−0.0011 (8)−0.0051 (8)0.0136 (8)
O40.0406 (7)0.0441 (8)0.0477 (8)0.0006 (6)0.0034 (6)−0.0032 (6)
C10.0329 (10)0.0591 (13)0.0383 (10)−0.0002 (8)0.0104 (8)0.0039 (9)
C20.0465 (12)0.0679 (15)0.0478 (12)−0.0094 (10)0.0056 (9)0.0003 (10)
C30.0515 (13)0.092 (2)0.0534 (13)−0.0177 (13)0.0049 (11)−0.0072 (13)
C40.0443 (13)0.118 (2)0.0443 (13)−0.0070 (14)−0.0007 (10)0.0093 (14)
C50.0421 (12)0.098 (2)0.0498 (13)0.0085 (13)0.0078 (10)0.0199 (13)
C60.0367 (10)0.0675 (14)0.0442 (11)0.0060 (9)0.0127 (9)0.0108 (10)
C70.0541 (13)0.0563 (14)0.0599 (13)0.0134 (11)0.0124 (11)0.0145 (11)
C80.0574 (13)0.0458 (13)0.0615 (13)0.0057 (10)0.0104 (11)0.0033 (10)
C90.0364 (10)0.0466 (11)0.0444 (10)0.0023 (8)0.0082 (8)0.0011 (9)
C100.0319 (9)0.0480 (11)0.0392 (10)0.0002 (8)0.0084 (8)0.0028 (8)
C110.0387 (10)0.0414 (11)0.0436 (10)−0.0016 (8)0.0082 (8)0.0009 (8)
C120.0350 (9)0.0430 (11)0.0441 (10)0.0011 (8)0.0096 (8)0.0012 (8)
C130.0360 (10)0.0519 (13)0.0413 (10)0.0003 (9)0.0084 (8)0.0004 (9)
C140.0348 (10)0.0639 (14)0.0491 (11)0.0011 (9)0.0009 (9)−0.0112 (10)
C160.0497 (17)0.190 (4)0.075 (2)−0.017 (2)0.0200 (15)−0.028 (3)
C150.0501 (14)0.102 (2)0.0630 (15)−0.0128 (13)0.0048 (12)−0.0044 (14)
C190.0656 (17)0.072 (2)0.124 (3)0.0113 (14)0.0167 (17)−0.0006 (18)
C170.0517 (18)0.186 (5)0.124 (3)0.007 (3)0.011 (2)−0.077 (3)
C180.091 (3)0.094 (3)0.170 (4)0.035 (2)0.007 (3)−0.037 (3)
S1—O11.410 (2)C7—C81.360 (3)
S1—O21.425 (2)C7—H70.93
S1—N11.650 (2)C8—C91.393 (3)
S1—C141.742 (2)C8—H80.93
N1—C131.383 (3)C9—C101.376 (3)
N1—H1N0.79 (2)C10—C111.422 (3)
O3—C131.207 (2)C11—C121.346 (3)
O4—C91.369 (2)C11—H110.93
O4—C121.379 (2)C12—C131.461 (3)
C1—C21.400 (3)C14—C191.360 (4)
C1—C61.419 (3)C14—C151.377 (3)
C1—C101.436 (3)C16—C171.316 (6)
C2—C31.371 (3)C16—C151.362 (5)
C2—H20.93C16—H160.93
C3—C41.393 (4)C15—H150.93
C3—H30.93C19—C181.412 (5)
C4—C51.350 (4)C19—H190.93
C4—H40.93C17—C181.346 (6)
C5—C61.419 (3)C17—H170.93
C5—H50.93C18—H180.93
C6—C71.418 (3)
O1—S1—O2120.71 (14)O4—C9—C10110.56 (17)
O1—S1—N1103.77 (12)O4—C9—C8124.53 (19)
O2—S1—N1108.08 (11)C10—C9—C8124.91 (19)
O1—S1—C14108.85 (12)C9—C10—C11106.10 (17)
O2—S1—C14107.57 (12)C9—C10—C1119.19 (18)
N1—S1—C14107.12 (10)C11—C10—C1134.70 (19)
C13—N1—S1125.68 (18)C12—C11—C10106.48 (18)
C13—N1—H1N121.3 (19)C12—C11—H11126.8
S1—N1—H1N111.1 (19)C10—C11—H11126.8
C9—O4—C12105.34 (15)C11—C12—O4111.50 (17)
C2—C1—C6119.94 (19)C11—C12—C13131.45 (19)
C2—C1—C10123.80 (19)O4—C12—C13117.01 (17)
C6—C1—C10116.25 (19)O3—C13—N1122.6 (2)
C3—C2—C1119.9 (2)O3—C13—C12123.26 (19)
C3—C2—H2120.1N1—C13—C12114.10 (19)
C1—C2—H2120.1C19—C14—C15120.1 (2)
C2—C3—C4120.7 (2)C19—C14—S1120.5 (2)
C2—C3—H3119.7C15—C14—S1119.4 (2)
C4—C3—H3119.7C17—C16—C15120.4 (4)
C5—C4—C3120.6 (2)C17—C16—H16119.8
C5—C4—H4119.7C15—C16—H16119.8
C3—C4—H4119.7C16—C15—C14120.1 (4)
C4—C5—C6121.1 (2)C16—C15—H15119.9
C4—C5—H5119.4C14—C15—H15119.9
C6—C5—H5119.4C14—C19—C18117.7 (3)
C1—C6—C5117.8 (2)C14—C19—H19121.2
C1—C6—C7120.97 (19)C18—C19—H19121.2
C5—C6—C7121.2 (2)C16—C17—C18121.4 (4)
C8—C7—C6122.3 (2)C16—C17—H17119.3
C8—C7—H7118.8C18—C17—H17119.3
C6—C7—H7118.8C17—C18—C19120.2 (4)
C7—C8—C9116.4 (2)C17—C18—H18119.9
C7—C8—H8121.8C19—C18—H18119.9
C9—C8—H8121.8
O1—S1—N1—C13179.8 (2)C6—C1—C10—C11179.5 (2)
O2—S1—N1—C1350.5 (2)C9—C10—C11—C120.6 (2)
C14—S1—N1—C13−65.2 (2)C1—C10—C11—C12−178.9 (2)
C6—C1—C2—C3−0.8 (3)C10—C11—C12—O4−0.9 (2)
C10—C1—C2—C3178.7 (2)C10—C11—C12—C13177.01 (19)
C1—C2—C3—C40.1 (4)C9—O4—C12—C110.8 (2)
C2—C3—C4—C50.2 (4)C9—O4—C12—C13−177.41 (15)
C3—C4—C5—C60.2 (4)S1—N1—C13—O3−2.0 (3)
C2—C1—C6—C51.1 (3)S1—N1—C13—C12177.46 (15)
C10—C1—C6—C5−178.44 (17)C11—C12—C13—O33.4 (3)
C2—C1—C6—C7179.6 (2)O4—C12—C13—O3−178.81 (18)
C10—C1—C6—C70.0 (3)C11—C12—C13—N1−176.1 (2)
C4—C5—C6—C1−0.8 (3)O4—C12—C13—N11.7 (2)
C4—C5—C6—C7−179.3 (2)O1—S1—C14—C19−147.8 (2)
C1—C6—C7—C80.1 (3)O2—S1—C14—C19−15.4 (2)
C5—C6—C7—C8178.5 (2)N1—S1—C14—C19100.6 (2)
C6—C7—C8—C9−0.3 (3)O1—S1—C14—C1532.2 (2)
C12—O4—C9—C10−0.4 (2)O2—S1—C14—C15164.60 (19)
C12—O4—C9—C8179.38 (19)N1—S1—C14—C15−79.4 (2)
C7—C8—C9—O4−179.39 (19)C17—C16—C15—C14−1.1 (5)
C7—C8—C9—C100.4 (3)C19—C14—C15—C163.4 (4)
O4—C9—C10—C11−0.1 (2)S1—C14—C15—C16−176.6 (2)
C8—C9—C10—C11−179.9 (2)C15—C14—C19—C18−2.7 (4)
O4—C9—C10—C1179.47 (15)S1—C14—C19—C18177.3 (3)
C8—C9—C10—C1−0.3 (3)C15—C16—C17—C18−2.0 (6)
C2—C1—C10—C9−179.43 (19)C16—C17—C18—C192.7 (7)
C6—C1—C10—C90.1 (3)C14—C19—C18—C17−0.3 (6)
C2—C1—C10—C110.0 (3)
D—H···AD—HH···AD···AD—H···A
N1—H1N···O40.79 (3)2.33 (3)2.653 (2)106 (2)
C19—H19···O20.932.552.890 (4)102.
N1—H1N···O2i0.79 (3)2.66 (1)3.057 (2)113 (2)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N1—H1N⋯O40.79 (3)2.33 (3)2.653 (2)106 (2)
N1—H1N⋯O2i0.79 (3)2.66 (1)3.057 (2)113 (2)

Symmetry code: (i) .

  3 in total

1.  A short history of SHELX.

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

2.  N-(Phenyl-sulfon-yl)acetamide.

Authors:  B Thimme Gowda; Sabine Foro; P G Nirmala; Hartmut Fuess
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-05-08

3.  N-Benzo-ylbenzene-sulfonamide.

Authors:  B Thimme Gowda; Sabine Foro; P A Suchetan; Hartmut Fuess
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2009-09-26
  3 in total

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