organic compounds
N-(2,3-Dihydro-1,4-benzodioxin-6-yl)-4-fluorobenzenesulfonamide
aMaterials Chemistry Laboratory, Department of Chemistry, GC University, Lahore 54000, Pakistan, bDepartment of Chemistry, University of Aberdeen, Meston Walk, Aberdeen AB24 3UE, Scotland, cQuestioned Documents Unit, Punjab Forensic Science Agency, Home Department, Lahore, Pakistan, and dThe Center of Excellence for Advanced Materials Research (CEAMR), Faculty of Science, King Abdulaziz University, PO Box 80203, Jeddah 21589, Saudi Arabia
*Correspondence e-mail: koolmuneeb@yahoo.com
In the title compound, C14H12FNO4S, the dihedral angle between the aromatic rings is 50.26 (9)° and the C—S—N—C bond adopts a gauche conformation [torsion angle = −68.12 (15)°]. The dihydrodioxine ring is disordered over two orientations, which both approximate to half-chairs, in a 0.880 (7):0.120 (7) ratio. In the crystal, N—H⋯O hydrogen bonds link the molecules into C(4) chains propagating in [100]. Weak C—H⋯O and C—H⋯F interactions consolidate the packing.
Experimental
Crystal data
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Data collection
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Refinement
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Data collection: APEX2 (Bruker, 2007); cell SAINT (Bruker, 2007); data reduction: SAINT; 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/S1600536812030863/bt5970sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812030863/bt5970Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812030863/bt5970Isup3.cml
0.2 g of 6-amino 1,4-benzodioxan was dissolved in 15 ml dichloromethane and 0.25 g of 4-fluorobenzene sulfonyl chloride was added to the mixture, which was stirred at room temperature overnight. The pH was maintained at 8–9 with triethyamine. On completion of reaction (after TLC) the pH was adjusted to 1–2 with 1 M HCl solution. The organic fraction was collected and the solvent was allowed to evaporate at room temperature. Colourless prisms of (I) were obtained in 95% yield.
The N-bond H atom was located in a difference map and its position was freely refined. The C-bound H atoms were placed in calculated positions (C—H = 0.93–0.97 Å) and refined as riding. The constraint Uiso(H) = 1.2Ueq(C,N) was applied.
The title compound, (I), (Fig. 1) was examined as part of our ongoing interest in the structural chemistry of
(Khan et al., 2011). A number of related structures have been reported by Gelbrich et al. (2007).The dihedral angle between the C1—C6 and C7—C12 benzene rings in (I) is 50.26 (9)°. The C1—S1—N1—C7 linkage adopts a
conformation [torsion angle = -68.12 (15)°] and the bond-angle sum about N1 (H atom coordinates freely refined) is 347.2°, possibly suggesting a state intermediate between sp2 and sp3. The largest bond angle at the distorted tetrahedral S atom is O1—S1—O2 [120.26 (9)°], which is typical for this class of compound (Khan et al., 2011).Atoms C13 and C14 and their attached H atoms of the dihydro-dioxin ring are disordered over two sets of sites in a 0.880 (7):0.120 (7) ratio. Both major and minor conformations approximate to a half-chair. In the major conformation, C13 and C14 are displaced from the plane defined by C7—C12/O3/O4 (r.m.s. deviation = 0.037 Å) by 0.212 (3) and -0.556 (3) Å, respectively. The equivalent atoms in the minor component are displaced by -0.44 (3) and 0.41 (2) Å, respectively.
In the crystal, the molecules are linked by N—H···O hydrogen bonds (Table 1) to generate C(4) chains propagating in [100] (Figure 2). Weak C—H···O and C—H···F interactions also occur but there is no aromatic π-π stacking in the structure of (I).
For related structures, see: Khan et al. (2011); Gelbrich et al. (2007).
Data collection: APEX2 (Bruker, 2007); cell
SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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).C14H12FNO4S | F(000) = 640 |
Mr = 309.31 | Dx = 1.489 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 5.1542 (5) Å | Cell parameters from 1453 reflections |
b = 22.237 (3) Å | θ = 2.5–25.5° |
c = 12.0706 (13) Å | µ = 0.26 mm−1 |
β = 94.422 (3)° | T = 296 K |
V = 1379.3 (3) Å3 | Prism, colourless |
Z = 4 | 0.39 × 0.34 × 0.23 mm |
Bruker APEXII CCD diffractometer | 2336 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.024 |
Graphite monochromator | θmax = 27.5°, θmin = 1.8° |
ω scans | h = −6→5 |
11762 measured reflections | k = −28→28 |
3156 independent reflections | l = −15→14 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.101 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0451P)2 + 0.3224P] where P = (Fo2 + 2Fc2)/3 |
3156 reflections | (Δ/σ)max < 0.001 |
202 parameters | Δρmax = 0.24 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
C14H12FNO4S | V = 1379.3 (3) Å3 |
Mr = 309.31 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 5.1542 (5) Å | µ = 0.26 mm−1 |
b = 22.237 (3) Å | T = 296 K |
c = 12.0706 (13) Å | 0.39 × 0.34 × 0.23 mm |
β = 94.422 (3)° |
Bruker APEXII CCD diffractometer | 2336 reflections with I > 2σ(I) |
11762 measured reflections | Rint = 0.024 |
3156 independent reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.101 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.02 | Δρmax = 0.24 e Å−3 |
3156 reflections | Δρmin = −0.32 e Å−3 |
202 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 | Occ. (<1) | |
C1 | 0.5881 (3) | 0.25665 (7) | 0.60034 (14) | 0.0404 (4) | |
C2 | 0.7189 (4) | 0.23608 (9) | 0.51210 (17) | 0.0565 (5) | |
H2 | 0.8515 | 0.2590 | 0.4852 | 0.068* | |
C3 | 0.6514 (5) | 0.18133 (10) | 0.46402 (18) | 0.0664 (6) | |
H3 | 0.7375 | 0.1668 | 0.4046 | 0.080* | |
C4 | 0.4572 (4) | 0.14930 (9) | 0.50536 (17) | 0.0564 (5) | |
C5 | 0.3224 (4) | 0.16869 (8) | 0.59056 (17) | 0.0543 (5) | |
H5 | 0.1876 | 0.1458 | 0.6154 | 0.065* | |
C6 | 0.3891 (4) | 0.22311 (8) | 0.63959 (15) | 0.0482 (4) | |
H6 | 0.3006 | 0.2371 | 0.6987 | 0.058* | |
F1 | 0.3949 (3) | 0.09489 (6) | 0.45976 (12) | 0.0886 (4) | |
C7 | 0.4989 (3) | 0.39470 (7) | 0.48965 (15) | 0.0429 (4) | |
C8 | 0.6750 (3) | 0.43897 (7) | 0.46691 (15) | 0.0434 (4) | |
H8 | 0.7859 | 0.4549 | 0.5239 | 0.052* | |
C9 | 0.6860 (3) | 0.45950 (7) | 0.35926 (14) | 0.0415 (4) | |
C10 | 0.5168 (3) | 0.43651 (8) | 0.27495 (15) | 0.0457 (4) | |
C11 | 0.3469 (4) | 0.39124 (9) | 0.29867 (18) | 0.0613 (5) | |
H11 | 0.2378 | 0.3746 | 0.2417 | 0.074* | |
C12 | 0.3366 (4) | 0.37037 (9) | 0.40506 (18) | 0.0583 (5) | |
H12 | 0.2208 | 0.3399 | 0.4202 | 0.070* | |
C13 | 0.8923 (7) | 0.51508 (15) | 0.2265 (2) | 0.0598 (8) | 0.880 (7) |
H13A | 1.0029 | 0.4842 | 0.1985 | 0.072* | 0.880 (7) |
H13B | 0.9770 | 0.5536 | 0.2185 | 0.072* | 0.880 (7) |
C13A | 0.794 (6) | 0.5341 (11) | 0.2265 (19) | 0.064 (7)* | 0.120 (7) |
H13C | 0.6299 | 0.5555 | 0.2269 | 0.076* | 0.120 (7) |
H13D | 0.9283 | 0.5628 | 0.2111 | 0.076* | 0.120 (7) |
C14 | 0.6350 (6) | 0.51509 (11) | 0.1600 (2) | 0.0578 (9) | 0.880 (7) |
H14A | 0.5239 | 0.5459 | 0.1879 | 0.069* | 0.880 (7) |
H14B | 0.6601 | 0.5241 | 0.0830 | 0.069* | 0.880 (7) |
C14A | 0.775 (4) | 0.4882 (9) | 0.1419 (15) | 0.058 (6)* | 0.120 (7) |
H14C | 0.9199 | 0.4603 | 0.1504 | 0.070* | 0.120 (7) |
H14D | 0.7654 | 0.5054 | 0.0679 | 0.070* | 0.120 (7) |
S1 | 0.66702 (8) | 0.32659 (2) | 0.66316 (4) | 0.04491 (14) | |
N1 | 0.4773 (3) | 0.37724 (7) | 0.60361 (14) | 0.0490 (4) | |
H1 | 0.330 (4) | 0.3731 (9) | 0.6218 (16) | 0.059* | |
O1 | 0.5996 (3) | 0.32377 (7) | 0.77539 (11) | 0.0620 (4) | |
O2 | 0.9274 (2) | 0.34095 (6) | 0.63905 (12) | 0.0603 (4) | |
O3 | 0.8603 (2) | 0.50425 (6) | 0.34055 (10) | 0.0564 (4) | |
O4 | 0.5128 (3) | 0.45743 (6) | 0.16736 (11) | 0.0586 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0334 (9) | 0.0456 (9) | 0.0420 (9) | 0.0026 (7) | 0.0025 (7) | 0.0036 (7) |
C2 | 0.0493 (12) | 0.0695 (12) | 0.0524 (11) | −0.0057 (9) | 0.0153 (9) | −0.0025 (9) |
C3 | 0.0714 (15) | 0.0770 (14) | 0.0526 (12) | 0.0018 (11) | 0.0160 (10) | −0.0162 (10) |
C4 | 0.0634 (14) | 0.0503 (10) | 0.0537 (12) | 0.0027 (9) | −0.0074 (10) | −0.0055 (9) |
C5 | 0.0500 (12) | 0.0474 (10) | 0.0659 (13) | −0.0054 (8) | 0.0062 (9) | 0.0070 (9) |
C6 | 0.0437 (11) | 0.0485 (9) | 0.0536 (11) | 0.0015 (8) | 0.0120 (8) | 0.0043 (8) |
F1 | 0.1154 (12) | 0.0617 (8) | 0.0870 (10) | −0.0070 (7) | −0.0023 (8) | −0.0230 (7) |
C7 | 0.0333 (9) | 0.0413 (8) | 0.0543 (11) | 0.0025 (7) | 0.0050 (7) | −0.0014 (7) |
C8 | 0.0368 (9) | 0.0424 (9) | 0.0500 (10) | −0.0032 (7) | −0.0025 (7) | −0.0069 (7) |
C9 | 0.0337 (9) | 0.0372 (8) | 0.0530 (10) | −0.0017 (6) | 0.0007 (7) | −0.0061 (7) |
C10 | 0.0435 (10) | 0.0427 (9) | 0.0500 (11) | 0.0015 (7) | −0.0034 (8) | −0.0053 (7) |
C11 | 0.0547 (13) | 0.0606 (12) | 0.0653 (13) | −0.0182 (9) | −0.0154 (10) | −0.0056 (10) |
C12 | 0.0457 (11) | 0.0553 (11) | 0.0725 (14) | −0.0174 (9) | −0.0049 (9) | 0.0033 (10) |
C13 | 0.0550 (18) | 0.0660 (17) | 0.0580 (16) | −0.0102 (14) | 0.0026 (12) | 0.0107 (12) |
C14 | 0.0650 (19) | 0.0518 (13) | 0.0555 (15) | −0.0002 (11) | −0.0029 (12) | 0.0041 (10) |
S1 | 0.0329 (2) | 0.0524 (3) | 0.0494 (3) | −0.00419 (18) | 0.00263 (17) | −0.00209 (19) |
N1 | 0.0342 (8) | 0.0510 (8) | 0.0630 (10) | 0.0015 (7) | 0.0122 (7) | 0.0001 (7) |
O1 | 0.0648 (9) | 0.0763 (9) | 0.0449 (8) | −0.0063 (7) | 0.0039 (6) | −0.0058 (6) |
O2 | 0.0297 (7) | 0.0679 (9) | 0.0833 (10) | −0.0074 (6) | 0.0038 (6) | −0.0003 (7) |
O3 | 0.0567 (9) | 0.0584 (8) | 0.0529 (8) | −0.0218 (6) | −0.0032 (6) | 0.0030 (6) |
O4 | 0.0665 (9) | 0.0568 (8) | 0.0505 (8) | −0.0093 (6) | −0.0090 (6) | −0.0024 (6) |
C1—C6 | 1.381 (2) | C11—C12 | 1.370 (3) |
C1—C2 | 1.381 (2) | C11—H11 | 0.9300 |
C1—S1 | 1.7640 (17) | C12—H12 | 0.9300 |
C2—C3 | 1.382 (3) | C13—O3 | 1.419 (3) |
C2—H2 | 0.9300 | C13—C14 | 1.496 (4) |
C3—C4 | 1.355 (3) | C13—H13A | 0.9700 |
C3—H3 | 0.9300 | C13—H13B | 0.9700 |
C4—C5 | 1.355 (3) | C13A—C14A | 1.44 (3) |
C4—F1 | 1.357 (2) | C13A—O3 | 1.54 (2) |
C5—C6 | 1.379 (3) | C13A—H13C | 0.9700 |
C5—H5 | 0.9300 | C13A—H13D | 0.9700 |
C6—H6 | 0.9300 | C14—O4 | 1.434 (3) |
C7—C12 | 1.379 (2) | C14—H14A | 0.9700 |
C7—C8 | 1.381 (2) | C14—H14B | 0.9700 |
C7—N1 | 1.442 (2) | C14A—O4 | 1.566 (18) |
C8—C9 | 1.383 (2) | C14A—H14C | 0.9700 |
C8—H8 | 0.9300 | C14A—H14D | 0.9700 |
C9—O3 | 1.371 (2) | S1—O1 | 1.4256 (14) |
C9—C10 | 1.386 (2) | S1—O2 | 1.4312 (13) |
C10—O4 | 1.378 (2) | S1—N1 | 1.6228 (16) |
C10—C11 | 1.379 (3) | N1—H1 | 0.81 (2) |
C6—C1—C2 | 120.33 (17) | O3—C13—H13A | 109.5 |
C6—C1—S1 | 118.77 (13) | C14—C13—H13A | 109.5 |
C2—C1—S1 | 120.88 (14) | O3—C13—H13B | 109.5 |
C1—C2—C3 | 119.58 (19) | C14—C13—H13B | 109.5 |
C1—C2—H2 | 120.2 | H13A—C13—H13B | 108.1 |
C3—C2—H2 | 120.2 | C14A—C13A—O3 | 109.0 (18) |
C4—C3—C2 | 118.54 (19) | C14A—C13A—H13C | 109.9 |
C4—C3—H3 | 120.7 | O3—C13A—H13C | 109.9 |
C2—C3—H3 | 120.7 | C14A—C13A—H13D | 109.9 |
C3—C4—C5 | 123.30 (19) | O3—C13A—H13D | 109.9 |
C3—C4—F1 | 118.53 (19) | H13C—C13A—H13D | 108.3 |
C5—C4—F1 | 118.17 (19) | O4—C14—C13 | 110.0 (2) |
C4—C5—C6 | 118.64 (18) | O4—C14—H14A | 109.7 |
C4—C5—H5 | 120.7 | C13—C14—H14A | 109.7 |
C6—C5—H5 | 120.7 | O4—C14—H14B | 109.7 |
C5—C6—C1 | 119.59 (17) | C13—C14—H14B | 109.7 |
C5—C6—H6 | 120.2 | H14A—C14—H14B | 108.2 |
C1—C6—H6 | 120.2 | C13A—C14A—O4 | 100.5 (18) |
C12—C7—C8 | 120.18 (17) | C13A—C14A—H14C | 111.7 |
C12—C7—N1 | 120.90 (16) | O4—C14A—H14C | 111.7 |
C8—C7—N1 | 118.81 (16) | C13A—C14A—H14D | 111.7 |
C7—C8—C9 | 119.83 (16) | O4—C14A—H14D | 111.7 |
C7—C8—H8 | 120.1 | H14C—C14A—H14D | 109.4 |
C9—C8—H8 | 120.1 | O1—S1—O2 | 120.26 (9) |
O3—C9—C8 | 117.99 (14) | O1—S1—N1 | 105.59 (9) |
O3—C9—C10 | 122.01 (16) | O2—S1—N1 | 107.32 (9) |
C8—C9—C10 | 119.95 (16) | O1—S1—C1 | 107.74 (8) |
O4—C10—C11 | 118.58 (16) | O2—S1—C1 | 107.34 (8) |
O4—C10—C9 | 122.02 (16) | N1—S1—C1 | 108.09 (8) |
C11—C10—C9 | 119.39 (17) | C7—N1—S1 | 121.42 (12) |
C12—C11—C10 | 120.85 (17) | C7—N1—H1 | 115.5 (14) |
C12—C11—H11 | 119.6 | S1—N1—H1 | 110.2 (15) |
C10—C11—H11 | 119.6 | C9—O3—C13 | 114.18 (15) |
C11—C12—C7 | 119.74 (17) | C9—O3—C13A | 110.9 (10) |
C11—C12—H12 | 120.1 | C10—O4—C14 | 112.66 (14) |
C7—C12—H12 | 120.1 | C10—O4—C14A | 112.4 (7) |
O3—C13—C14 | 110.8 (2) | ||
C6—C1—C2—C3 | −0.8 (3) | C2—C1—S1—O1 | −153.38 (16) |
S1—C1—C2—C3 | −179.50 (16) | C6—C1—S1—O2 | 158.72 (14) |
C1—C2—C3—C4 | 0.0 (3) | C2—C1—S1—O2 | −22.52 (18) |
C2—C3—C4—C5 | 1.1 (3) | C6—C1—S1—N1 | −85.80 (15) |
C2—C3—C4—F1 | −178.54 (19) | C2—C1—S1—N1 | 92.95 (16) |
C3—C4—C5—C6 | −1.5 (3) | C12—C7—N1—S1 | 97.69 (19) |
F1—C4—C5—C6 | 178.17 (17) | C8—C7—N1—S1 | −86.06 (19) |
C4—C5—C6—C1 | 0.7 (3) | O1—S1—N1—C7 | 176.79 (14) |
C2—C1—C6—C5 | 0.4 (3) | O2—S1—N1—C7 | 47.37 (16) |
S1—C1—C6—C5 | 179.15 (14) | C1—S1—N1—C7 | −68.12 (15) |
C12—C7—C8—C9 | 0.9 (3) | C8—C9—O3—C13 | 169.3 (2) |
N1—C7—C8—C9 | −175.37 (15) | C10—C9—O3—C13 | −13.3 (3) |
C7—C8—C9—O3 | 178.83 (15) | C8—C9—O3—C13A | −163.5 (11) |
C7—C8—C9—C10 | 1.3 (3) | C10—C9—O3—C13A | 13.9 (11) |
O3—C9—C10—O4 | −0.3 (3) | C14—C13—O3—C9 | 43.1 (3) |
C8—C9—C10—O4 | 177.12 (15) | C14—C13—O3—C13A | −45 (2) |
O3—C9—C10—C11 | 179.60 (17) | C14A—C13A—O3—C9 | −54 (2) |
C8—C9—C10—C11 | −3.0 (3) | C14A—C13A—O3—C13 | 48.9 (19) |
O4—C10—C11—C12 | −177.64 (18) | C11—C10—O4—C14 | 161.9 (2) |
C9—C10—C11—C12 | 2.5 (3) | C9—C10—O4—C14 | −18.2 (3) |
C10—C11—C12—C7 | −0.3 (3) | C11—C10—O4—C14A | −157.3 (9) |
C8—C7—C12—C11 | −1.5 (3) | C9—C10—O4—C14A | 22.6 (9) |
N1—C7—C12—C11 | 174.74 (18) | C13—C14—O4—C10 | 47.5 (3) |
O3—C13—C14—O4 | −61.6 (4) | C13—C14—O4—C14A | −50.3 (11) |
O3—C13A—C14A—O4 | 72 (2) | C13A—C14A—O4—C10 | −57.2 (18) |
C6—C1—S1—O1 | 27.86 (16) | C13A—C14A—O4—C14 | 41.3 (14) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.81 (2) | 2.22 (2) | 3.009 (2) | 164 (2) |
C3—H3···O1ii | 0.93 | 2.53 | 3.368 (3) | 150 |
C5—H5···O4iii | 0.93 | 2.56 | 3.391 (2) | 149 |
C8—H8···O3iv | 0.93 | 2.52 | 3.446 (2) | 172 |
C13—H13B···F1v | 0.97 | 2.48 | 3.129 (3) | 125 |
Symmetry codes: (i) x−1, y, z; (ii) x+1/2, −y+1/2, z−1/2; (iii) x−1/2, −y+1/2, z+1/2; (iv) −x+2, −y+1, −z+1; (v) −x+3/2, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C14H12FNO4S |
Mr | 309.31 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 296 |
a, b, c (Å) | 5.1542 (5), 22.237 (3), 12.0706 (13) |
β (°) | 94.422 (3) |
V (Å3) | 1379.3 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.26 |
Crystal size (mm) | 0.39 × 0.34 × 0.23 |
Data collection | |
Diffractometer | Bruker APEXII CCD |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11762, 3156, 2336 |
Rint | 0.024 |
(sin θ/λ)max (Å−1) | 0.649 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.101, 1.02 |
No. of reflections | 3156 |
No. of parameters | 202 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.24, −0.32 |
Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.81 (2) | 2.22 (2) | 3.009 (2) | 164 (2) |
C3—H3···O1ii | 0.93 | 2.53 | 3.368 (3) | 150 |
C5—H5···O4iii | 0.93 | 2.56 | 3.391 (2) | 149 |
C8—H8···O3iv | 0.93 | 2.52 | 3.446 (2) | 172 |
C13—H13B···F1v | 0.97 | 2.48 | 3.129 (3) | 125 |
Symmetry codes: (i) x−1, y, z; (ii) x+1/2, −y+1/2, z−1/2; (iii) x−1/2, −y+1/2, z+1/2; (iv) −x+2, −y+1, −z+1; (v) −x+3/2, y+1/2, −z+1/2. |
Acknowledgements
The authors are thankful to the Higher Education Commission of Pakistan for providing a grant under the project strengthening the Materials Chemistry Laboratory at GC University, Lahore.
References
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Gelbrich, T., Hursthouse, M. B. & Threlfall, T. L. (2007). Acta Cryst. B63, 621–632. Web of Science CSD CrossRef IUCr Journals Google Scholar
Khan, M. H., Khan, I. U., Arshad, M. N., Mughal, S. Y. & Akkurt, M. (2011). Acta Cryst. E67, o885–o886. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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The title compound, (I), (Fig. 1) was examined as part of our ongoing interest in the structural chemistry of sulfonamides (Khan et al., 2011). A number of related structures have been reported by Gelbrich et al. (2007).
The dihedral angle between the C1—C6 and C7—C12 benzene rings in (I) is 50.26 (9)°. The C1—S1—N1—C7 linkage adopts a gauche conformation [torsion angle = -68.12 (15)°] and the bond-angle sum about N1 (H atom coordinates freely refined) is 347.2°, possibly suggesting a hybridization state intermediate between sp2 and sp3. The largest bond angle at the distorted tetrahedral S atom is O1—S1—O2 [120.26 (9)°], which is typical for this class of compound (Khan et al., 2011).
Atoms C13 and C14 and their attached H atoms of the dihydro-dioxin ring are disordered over two sets of sites in a 0.880 (7):0.120 (7) ratio. Both major and minor conformations approximate to a half-chair. In the major conformation, C13 and C14 are displaced from the plane defined by C7—C12/O3/O4 (r.m.s. deviation = 0.037 Å) by 0.212 (3) and -0.556 (3) Å, respectively. The equivalent atoms in the minor component are displaced by -0.44 (3) and 0.41 (2) Å, respectively.
In the crystal, the molecules are linked by N—H···O hydrogen bonds (Table 1) to generate C(4) chains propagating in [100] (Figure 2). Weak C—H···O and C—H···F interactions also occur but there is no aromatic π-π stacking in the structure of (I).