organic compounds
N-(Phenylsulfonyl)naphtho[2,1-b]furan-1-carboxamide
aCenter for Advanced Materials and Department of Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India, bDepartment of PG Studies and Research in Physics, Tumkur University, Tumkur, Karnataka 572 103, India, and cDepartment of Chemistry, Kuvempu University, Shankaraghatta, Shimoga, Karnataka, India
*Correspondence e-mail: spal12pm@gmail.com
In the title compound, C19H13NO4S, the molecule is twisted at the S atom with a C—S—N—C torsion angle of −65.2 (2)° between the benzene ring and the –SO2—NH—C=O segment. The dihedral angle between the benzene and the naphthofuran ring system is 83.3 (1)°. In the crystal, molecules are linked by N—H⋯O hydrogen bonds into chains running along the c axis. An intramolecular N—H⋯O(furan) interaction is also observed.
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker, 2004); cell 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.
Supporting information
https://doi.org/10.1107/S1600536811050495/ds2146sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811050495/ds2146Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536811050495/ds2146Isup3.cml
The title compound was prepared by refluxing a mixture of naphthofuran-2-carboxylic acid (10 mmol),benzenesulfonamide(10 mmol) and phosphorous oxychloride for 1 h on a water bath.The resultant mixture was cooled and poured into ice cold water. The solid, N-(Naphthofuroyl)benzenesulfonamide obtained was filtered, washed thoroughly with water and then dissolved in sodium bicarbonate solution. The compound was later reprecipitated by acidifying the filtered solution with dilute hydrochloric acid. The filtered and dried compound was recrystallized to constant melting point. The compound was characterized by its characteristic carbonyl C=O stretching (1698.2 cm-1), N—H stretching (3233.1 cm-1), symmetric SO2(1173.3 cm-1) and asymmetric SO2 (1326.2 cm-1) infrared absorption frequencies. Single crystals suitable for x-ray diffraction were grown from a slow evaporation of its ethanolic solution at room temperature.
The H atom of the NH group was located in a difference map and later restrained to N—H = 0.86 (1)%A. The other H atoms were positioned with idealized geometry using a riding model with C—H = 0.93 Å. All H atoms were refined with isotropic displacement parameters (set to 1.2 times of the Ueq of the parent atom).
Aryl Acyl
are known as a potent antitumor agent against a broad spectrum of human tumor xenografts in nude mice. Further,the title compound exhibits antibacterial and antifungal activities (our unpublished results). In order to study the effect of the ring substituents on the solid-state structures of N-naphthofuroyl-sulfonamides, in the present work the structure of N-(Naphthofuroyl)benzenesulfonamide has been determined. The title compound (I) crystallizes in Monoclinic P21/c compared to N-(benzoyl)benzenesulfonamide (II) (Gowda et al., 2009) and N-(Phenylsulfonyl)acetamide (III)(Gowda et al., 2010) which crystallizes in Triclinic P-1 and Tetragonal P43space groups respectively. In III, the packing of molecules is linked by N—H···.O(C) hydrogen bonds and in II by N—H···.O(S) bonds, whereas in I, the molecules are linked by intermolecular N—H···.O(S) hydrogen bonds. Intramolecular C—H···..O(S) and N—H···..O(furan) interactions are also observed.The molecules are twisted at S atoms with the C—S(O2)—NH—C(O) torsion angle of -65.2 (2)°, compared to the values of -66.9 (3)° in (II) and -58.8 (4)° in (III). The dihedral angle between the benzene ring and the naphthofuran ring in (I) is 83.3 (1)°, compared to 80.3 (1)° observed between the two benzene rings in (II) and 38.7 (0)° in (III) between the benzene ring and the mean plane of CH3 fragement respectively. The packing of the molecules via intermolecular N—H···.O(S) hydrogen bonds is shown in Fig. 2.For related structures, see: Gowda et al. (2009, 2010).
Data collection: APEX2 (Bruker, 2004); cell
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 (Sheldrick, 2008).Fig. 1. Molecular structure of the title compound, showing the atom-labllling scheme. | |
Fig. 2. Molecular packing in the title compound. Hydrogen bonds are shown as dashed lines. |
C19H13NO4S | F(000) = 728 |
Mr = 351.36 | 1.447 Mg m-3 |
Monoclinic, P21/c | Dx = 1.447 Mg m−3 |
Hall symbol: -P 2ybc | Mo Kα radiation, λ = 0.71073 Å |
a = 13.8504 (10) Å | Cell parameters from 2986 reflections |
b = 12.2166 (8) Å | θ = 2.2° |
c = 9.7164 (6) Å | µ = 0.23 mm−1 |
β = 101.248 (2)° | T = 299 K |
V = 1612.48 (19) Å3 | Prism, colourless |
Z = 4 | 0.35 × 0.3 × 0.25 mm |
Bruker APEXII CCD area-detector diffractometer | 2986 independent reflections |
Radiation source: fine-focus sealed tube | 2394 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.027 |
phi and scans | θmax = 25.5°, θmin = 2.9° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −16→16 |
Tmin = 0.924, Tmax = 0.945 | k = −14→14 |
15289 measured reflections | l = −11→11 |
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)] = 0.041 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.133 | w = 1/[σ2(Fo2) + (0.0827P)2 + 1.1854P] where P = (Fo2 + 2Fc2)/3 |
S = 0.85 | (Δ/σ)max = 0.001 |
2986 reflections | Δρmax = 0.25 e Å−3 |
231 parameters | Δρmin = −0.38 e Å−3 |
1 restraint | Extinction correction: SHELXL |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0054 (12) |
C19H13NO4S | V = 1612.48 (19) Å3 |
Mr = 351.36 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.8504 (10) Å | µ = 0.23 mm−1 |
b = 12.2166 (8) Å | T = 299 K |
c = 9.7164 (6) Å | 0.35 × 0.3 × 0.25 mm |
β = 101.248 (2)° |
Bruker APEXII CCD area-detector diffractometer | 2986 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 2394 reflections with I > 2σ(I) |
Tmin = 0.924, Tmax = 0.945 | Rint = 0.027 |
15289 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 1 restraint |
wR(F2) = 0.133 | H atoms treated by a mixture of independent and constrained refinement |
S = 0.85 | Δρmax = 0.25 e Å−3 |
2986 reflections | Δρmin = −0.38 e Å−3 |
231 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
H1N | 0.8221 (19) | 0.1816 (19) | 0.346 (3) | 0.053 (8)* | |
S1 | 0.72588 (4) | 0.25754 (5) | 0.18450 (6) | 0.0566 (2) | |
N1 | 0.82025 (14) | 0.24177 (18) | 0.3158 (2) | 0.0527 (5) | |
O1 | 0.69636 (15) | 0.14945 (17) | 0.1467 (2) | 0.0910 (7) | |
O2 | 0.75502 (14) | 0.3299 (2) | 0.08507 (18) | 0.0853 (7) | |
O3 | 0.85990 (12) | 0.42070 (13) | 0.35980 (18) | 0.0626 (5) | |
O4 | 0.96215 (10) | 0.17651 (11) | 0.52390 (14) | 0.0448 (4) | |
C1 | 1.14610 (14) | 0.26862 (18) | 0.8155 (2) | 0.0430 (5) | |
C2 | 1.18623 (16) | 0.3662 (2) | 0.8774 (2) | 0.0545 (6) | |
H2 | 1.1644 | 0.4332 | 0.8376 | 0.065* | |
C3 | 1.25770 (18) | 0.3628 (3) | 0.9968 (2) | 0.0663 (7) | |
H3 | 1.2841 | 0.4278 | 1.0377 | 0.08* | |
C4 | 1.29114 (18) | 0.2631 (3) | 1.0575 (3) | 0.0703 (8) | |
H4 | 1.3395 | 0.2621 | 1.1387 | 0.084* | |
C5 | 1.25403 (17) | 0.1678 (3) | 0.9995 (2) | 0.0636 (7) | |
H5 | 1.2771 | 0.102 | 1.0416 | 0.076* | |
C6 | 1.18038 (15) | 0.16646 (19) | 0.8755 (2) | 0.0488 (5) | |
C7 | 1.14042 (17) | 0.0666 (2) | 0.8153 (2) | 0.0566 (6) | |
H7 | 1.1644 | 0.0011 | 0.8573 | 0.068* | |
C8 | 1.06823 (17) | 0.06330 (19) | 0.6984 (2) | 0.0550 (6) | |
H8 | 1.0426 | −0.0025 | 0.6593 | 0.066* | |
C9 | 1.03480 (14) | 0.16388 (17) | 0.6404 (2) | 0.0425 (5) | |
C10 | 1.06976 (14) | 0.26419 (16) | 0.6922 (2) | 0.0395 (4) | |
C11 | 1.01546 (14) | 0.34374 (17) | 0.6020 (2) | 0.0412 (4) | |
H11 | 1.0225 | 0.4194 | 0.609 | 0.049* | |
C12 | 0.95188 (13) | 0.28806 (17) | 0.5044 (2) | 0.0404 (4) | |
C13 | 0.87507 (14) | 0.32539 (18) | 0.3889 (2) | 0.0430 (5) | |
C14 | 0.63289 (15) | 0.3220 (2) | 0.2518 (2) | 0.0502 (5) | |
C16 | 0.4993 (2) | 0.3091 (5) | 0.3712 (4) | 0.1040 (13) | |
H16 | 0.4601 | 0.2673 | 0.4186 | 0.125* | |
C15 | 0.57551 (19) | 0.2612 (3) | 0.3241 (3) | 0.0725 (8) | |
H15 | 0.5888 | 0.1872 | 0.3409 | 0.087* | |
C19 | 0.6169 (2) | 0.4313 (3) | 0.2335 (4) | 0.0876 (9) | |
H19 | 0.6567 | 0.4741 | 0.1882 | 0.105* | |
C17 | 0.4807 (3) | 0.4141 (5) | 0.3499 (5) | 0.1213 (18) | |
H17 | 0.4271 | 0.445 | 0.3801 | 0.146* | |
C18 | 0.5377 (3) | 0.4776 (4) | 0.2854 (5) | 0.1210 (15) | |
H18 | 0.5249 | 0.5522 | 0.275 | 0.145* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0409 (3) | 0.0788 (5) | 0.0460 (3) | 0.0105 (3) | −0.0012 (2) | −0.0159 (3) |
N1 | 0.0427 (10) | 0.0551 (13) | 0.0552 (11) | 0.0046 (8) | −0.0028 (8) | −0.0053 (9) |
O1 | 0.0699 (12) | 0.0851 (14) | 0.1006 (15) | 0.0202 (10) | −0.0264 (11) | −0.0464 (12) |
O2 | 0.0582 (10) | 0.154 (2) | 0.0440 (9) | 0.0078 (12) | 0.0119 (8) | 0.0091 (11) |
O3 | 0.0571 (9) | 0.0564 (10) | 0.0672 (10) | −0.0011 (8) | −0.0051 (8) | 0.0136 (8) |
O4 | 0.0406 (7) | 0.0441 (8) | 0.0477 (8) | 0.0006 (6) | 0.0034 (6) | −0.0032 (6) |
C1 | 0.0329 (10) | 0.0591 (13) | 0.0383 (10) | −0.0002 (8) | 0.0104 (8) | 0.0039 (9) |
C2 | 0.0465 (12) | 0.0679 (15) | 0.0478 (12) | −0.0094 (10) | 0.0056 (9) | 0.0003 (10) |
C3 | 0.0515 (13) | 0.092 (2) | 0.0534 (13) | −0.0177 (13) | 0.0049 (11) | −0.0072 (13) |
C4 | 0.0443 (13) | 0.118 (2) | 0.0443 (13) | −0.0070 (14) | −0.0007 (10) | 0.0093 (14) |
C5 | 0.0421 (12) | 0.098 (2) | 0.0498 (13) | 0.0085 (13) | 0.0078 (10) | 0.0199 (13) |
C6 | 0.0367 (10) | 0.0675 (14) | 0.0442 (11) | 0.0060 (9) | 0.0127 (9) | 0.0108 (10) |
C7 | 0.0541 (13) | 0.0563 (14) | 0.0599 (13) | 0.0134 (11) | 0.0124 (11) | 0.0145 (11) |
C8 | 0.0574 (13) | 0.0458 (13) | 0.0615 (13) | 0.0057 (10) | 0.0104 (11) | 0.0033 (10) |
C9 | 0.0364 (10) | 0.0466 (11) | 0.0444 (10) | 0.0023 (8) | 0.0082 (8) | 0.0011 (9) |
C10 | 0.0319 (9) | 0.0480 (11) | 0.0392 (10) | 0.0002 (8) | 0.0084 (8) | 0.0028 (8) |
C11 | 0.0387 (10) | 0.0414 (11) | 0.0436 (10) | −0.0016 (8) | 0.0082 (8) | 0.0009 (8) |
C12 | 0.0350 (9) | 0.0430 (11) | 0.0441 (10) | 0.0011 (8) | 0.0096 (8) | 0.0012 (8) |
C13 | 0.0360 (10) | 0.0519 (13) | 0.0413 (10) | 0.0003 (9) | 0.0084 (8) | 0.0004 (9) |
C14 | 0.0348 (10) | 0.0639 (14) | 0.0491 (11) | 0.0011 (9) | 0.0009 (9) | −0.0112 (10) |
C16 | 0.0497 (17) | 0.190 (4) | 0.075 (2) | −0.017 (2) | 0.0200 (15) | −0.028 (3) |
C15 | 0.0501 (14) | 0.102 (2) | 0.0630 (15) | −0.0128 (13) | 0.0048 (12) | −0.0044 (14) |
C19 | 0.0656 (17) | 0.072 (2) | 0.124 (3) | 0.0113 (14) | 0.0167 (17) | −0.0006 (18) |
C17 | 0.0517 (18) | 0.186 (5) | 0.124 (3) | 0.007 (3) | 0.011 (2) | −0.077 (3) |
C18 | 0.091 (3) | 0.094 (3) | 0.170 (4) | 0.035 (2) | 0.007 (3) | −0.037 (3) |
S1—O1 | 1.410 (2) | C7—C8 | 1.360 (3) |
S1—O2 | 1.425 (2) | C7—H7 | 0.93 |
S1—N1 | 1.650 (2) | C8—C9 | 1.393 (3) |
S1—C14 | 1.742 (2) | C8—H8 | 0.93 |
N1—C13 | 1.383 (3) | C9—C10 | 1.376 (3) |
N1—H1N | 0.79 (2) | C10—C11 | 1.422 (3) |
O3—C13 | 1.207 (2) | C11—C12 | 1.346 (3) |
O4—C9 | 1.369 (2) | C11—H11 | 0.93 |
O4—C12 | 1.379 (2) | C12—C13 | 1.461 (3) |
C1—C2 | 1.400 (3) | C14—C19 | 1.360 (4) |
C1—C6 | 1.419 (3) | C14—C15 | 1.377 (3) |
C1—C10 | 1.436 (3) | C16—C17 | 1.316 (6) |
C2—C3 | 1.371 (3) | C16—C15 | 1.362 (5) |
C2—H2 | 0.93 | C16—H16 | 0.93 |
C3—C4 | 1.393 (4) | C15—H15 | 0.93 |
C3—H3 | 0.93 | C19—C18 | 1.412 (5) |
C4—C5 | 1.350 (4) | C19—H19 | 0.93 |
C4—H4 | 0.93 | C17—C18 | 1.346 (6) |
C5—C6 | 1.419 (3) | C17—H17 | 0.93 |
C5—H5 | 0.93 | C18—H18 | 0.93 |
C6—C7 | 1.418 (3) | ||
O1—S1—O2 | 120.71 (14) | O4—C9—C10 | 110.56 (17) |
O1—S1—N1 | 103.77 (12) | O4—C9—C8 | 124.53 (19) |
O2—S1—N1 | 108.08 (11) | C10—C9—C8 | 124.91 (19) |
O1—S1—C14 | 108.85 (12) | C9—C10—C11 | 106.10 (17) |
O2—S1—C14 | 107.57 (12) | C9—C10—C1 | 119.19 (18) |
N1—S1—C14 | 107.12 (10) | C11—C10—C1 | 134.70 (19) |
C13—N1—S1 | 125.68 (18) | C12—C11—C10 | 106.48 (18) |
C13—N1—H1N | 121.3 (19) | C12—C11—H11 | 126.8 |
S1—N1—H1N | 111.1 (19) | C10—C11—H11 | 126.8 |
C9—O4—C12 | 105.34 (15) | C11—C12—O4 | 111.50 (17) |
C2—C1—C6 | 119.94 (19) | C11—C12—C13 | 131.45 (19) |
C2—C1—C10 | 123.80 (19) | O4—C12—C13 | 117.01 (17) |
C6—C1—C10 | 116.25 (19) | O3—C13—N1 | 122.6 (2) |
C3—C2—C1 | 119.9 (2) | O3—C13—C12 | 123.26 (19) |
C3—C2—H2 | 120.1 | N1—C13—C12 | 114.10 (19) |
C1—C2—H2 | 120.1 | C19—C14—C15 | 120.1 (2) |
C2—C3—C4 | 120.7 (2) | C19—C14—S1 | 120.5 (2) |
C2—C3—H3 | 119.7 | C15—C14—S1 | 119.4 (2) |
C4—C3—H3 | 119.7 | C17—C16—C15 | 120.4 (4) |
C5—C4—C3 | 120.6 (2) | C17—C16—H16 | 119.8 |
C5—C4—H4 | 119.7 | C15—C16—H16 | 119.8 |
C3—C4—H4 | 119.7 | C16—C15—C14 | 120.1 (4) |
C4—C5—C6 | 121.1 (2) | C16—C15—H15 | 119.9 |
C4—C5—H5 | 119.4 | C14—C15—H15 | 119.9 |
C6—C5—H5 | 119.4 | C14—C19—C18 | 117.7 (3) |
C1—C6—C5 | 117.8 (2) | C14—C19—H19 | 121.2 |
C1—C6—C7 | 120.97 (19) | C18—C19—H19 | 121.2 |
C5—C6—C7 | 121.2 (2) | C16—C17—C18 | 121.4 (4) |
C8—C7—C6 | 122.3 (2) | C16—C17—H17 | 119.3 |
C8—C7—H7 | 118.8 | C18—C17—H17 | 119.3 |
C6—C7—H7 | 118.8 | C17—C18—C19 | 120.2 (4) |
C7—C8—C9 | 116.4 (2) | C17—C18—H18 | 119.9 |
C7—C8—H8 | 121.8 | C19—C18—H18 | 119.9 |
C9—C8—H8 | 121.8 | ||
O1—S1—N1—C13 | 179.8 (2) | C6—C1—C10—C11 | 179.5 (2) |
O2—S1—N1—C13 | 50.5 (2) | C9—C10—C11—C12 | 0.6 (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—C3 | 178.7 (2) | C10—C11—C12—C13 | 177.01 (19) |
C1—C2—C3—C4 | 0.1 (4) | C9—O4—C12—C11 | 0.8 (2) |
C2—C3—C4—C5 | 0.2 (4) | C9—O4—C12—C13 | −177.41 (15) |
C3—C4—C5—C6 | 0.2 (4) | S1—N1—C13—O3 | −2.0 (3) |
C2—C1—C6—C5 | 1.1 (3) | S1—N1—C13—C12 | 177.46 (15) |
C10—C1—C6—C5 | −178.44 (17) | C11—C12—C13—O3 | 3.4 (3) |
C2—C1—C6—C7 | 179.6 (2) | O4—C12—C13—O3 | −178.81 (18) |
C10—C1—C6—C7 | 0.0 (3) | C11—C12—C13—N1 | −176.1 (2) |
C4—C5—C6—C1 | −0.8 (3) | O4—C12—C13—N1 | 1.7 (2) |
C4—C5—C6—C7 | −179.3 (2) | O1—S1—C14—C19 | −147.8 (2) |
C1—C6—C7—C8 | 0.1 (3) | O2—S1—C14—C19 | −15.4 (2) |
C5—C6—C7—C8 | 178.5 (2) | N1—S1—C14—C19 | 100.6 (2) |
C6—C7—C8—C9 | −0.3 (3) | O1—S1—C14—C15 | 32.2 (2) |
C12—O4—C9—C10 | −0.4 (2) | O2—S1—C14—C15 | 164.60 (19) |
C12—O4—C9—C8 | 179.38 (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—C10 | 0.4 (3) | C19—C14—C15—C16 | 3.4 (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—C1 | 179.47 (15) | S1—C14—C19—C18 | 177.3 (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—C19 | 2.7 (7) |
C6—C1—C10—C9 | 0.1 (3) | C14—C19—C18—C17 | −0.3 (6) |
C2—C1—C10—C11 | 0.0 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O4 | 0.79 (3) | 2.33 (3) | 2.653 (2) | 106 (2) |
C19—H19···O2 | 0.93 | 2.55 | 2.890 (4) | 102 |
N1—H1N···O2i | 0.79 (3) | 2.66 (1) | 3.057 (2) | 113 (2) |
Symmetry code: (i) x, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C19H13NO4S |
Mr | 351.36 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 299 |
a, b, c (Å) | 13.8504 (10), 12.2166 (8), 9.7164 (6) |
β (°) | 101.248 (2) |
V (Å3) | 1612.48 (19) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.23 |
Crystal size (mm) | 0.35 × 0.3 × 0.25 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.924, 0.945 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 15289, 2986, 2394 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.606 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.133, 0.85 |
No. of reflections | 2986 |
No. of parameters | 231 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.25, −0.38 |
Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT-Plus (Bruker, 2004), SAINT-Plus and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O4 | 0.79 (3) | 2.33 (3) | 2.653 (2) | 106 (2) |
N1—H1N···O2i | 0.79 (3) | 2.656 (3) | 3.057 (2) | 113 (2) |
Symmetry code: (i) x, −y+1/2, z+1/2. |
Acknowledgements
The authors acknowledge Dr K. Gunasekaran and Jagadeesan CAS in Crystallography and Biophysics, University of Madras, and Dr H. C. Devarajegowda, Yuvaraja's College, Mysore, for useful discusions. The Department of Chemistry, IIT Madras, is acknowledged for the data collection.
References
Bruker (2004). APEX2 and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Nirmala, P. G. & Fuess, H. (2010). Acta Cryst. E66, o1284. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Aryl Acyl sulfonamides are known as a potent antitumor agent against a broad spectrum of human tumor xenografts in nude mice. Further,the title compound exhibits antibacterial and antifungal activities (our unpublished results). In order to study the effect of the ring substituents on the solid-state structures of N-naphthofuroyl-sulfonamides, in the present work the structure of N-(Naphthofuroyl)benzenesulfonamide has been determined. The title compound (I) crystallizes in Monoclinic P21/c space group compared to N-(benzoyl)benzenesulfonamide (II) (Gowda et al., 2009) and N-(Phenylsulfonyl)acetamide (III)(Gowda et al., 2010) which crystallizes in Triclinic P-1 and Tetragonal P43space groups respectively. In III, the packing of molecules is linked by N—H···.O(C) hydrogen bonds and in II by N—H···.O(S) bonds, whereas in I, the molecules are linked by intermolecular N—H···.O(S) hydrogen bonds. Intramolecular C—H···..O(S) and N—H···..O(furan) interactions are also observed.The molecules are twisted at S atoms with the C—S(O2)—NH—C(O) torsion angle of -65.2 (2)°, compared to the values of -66.9 (3)° in (II) and -58.8 (4)° in (III). The dihedral angle between the benzene ring and the naphthofuran ring in (I) is 83.3 (1)°, compared to 80.3 (1)° observed between the two benzene rings in (II) and 38.7 (0)° in (III) between the benzene ring and the mean plane of CH3 fragement respectively. The packing of the molecules via intermolecular N—H···.O(S) hydrogen bonds is shown in Fig. 2.