Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270105005160/sx1166sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270105005160/sx1166Isup2.hkl |
CCDC reference: 269047
A mixture of sodium saccharine (0.1 mol) and cinnamoyl chloride (0.1 mol) in tetrahydrofuran (100 ml) was stirred under reflux for 5 h. The precipitate of NaCl was filtered off. After filtration and evaporation of the solvent, the residual solid was recrystallized from tetrahydrofuran as colourless crystals of (I) (m.p. 497–501 K, 65% yield).
All H atoms were located in a difference Fourier map and their positional and isotropic displacement parameters were refined. The C—H bond lengths are in the range 0.91 (3)–1.00 (3) Å and the Uiso(H) values lie in the range 0.049 (6)–0.085 (9) Å2.
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1994); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN for Windows (Molecular Structure Corporation, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2000); software used to prepare material for publication: WinGX (Farrugia, 1999).
C16H11NO4S | F(000) = 1296 |
Mr = 313.32 | Dx = 1.425 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -C 2yc | Cell parameters from 3237 reflections |
a = 13.714 (3) Å | θ = 2.5–30.0° |
b = 10.456 (4) Å | µ = 0.24 mm−1 |
c = 20.781 (3) Å | T = 293 K |
β = 101.365 (5)° | Prism, colourless |
V = 2921.4 (14) Å3 | 0.75 × 0.65 × 0.50 mm |
Z = 8 |
Rigaku AFC-7S diffractometer | 2325 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.063 |
Graphite monochromator | θmax = 30.0°, θmin = 2.5° |
ω/2θ scans | h = −19→19 |
Absorption correction: for a sphere (Dwiggins, 1975) | k = −14→14 |
Tmin = 0.818, Tmax = 0.866 | l = −29→29 |
3054 measured reflections | 3 standard reflections every 150 reflections |
2939 independent reflections | intensity decay: −0.2% |
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)] = 0.045 | All H-atom parameters refined |
wR(F2) = 0.138 | w = 1/[σ2(Fo2) + (0.088P)2 + 1.695P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
2939 reflections | Δρmax = 0.42 e Å−3 |
244 parameters | Δρmin = −0.41 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0034 (7) |
C16H11NO4S | V = 2921.4 (14) Å3 |
Mr = 313.32 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 13.714 (3) Å | µ = 0.24 mm−1 |
b = 10.456 (4) Å | T = 293 K |
c = 20.781 (3) Å | 0.75 × 0.65 × 0.50 mm |
β = 101.365 (5)° |
Rigaku AFC-7S diffractometer | 2325 reflections with I > 2σ(I) |
Absorption correction: for a sphere (Dwiggins, 1975) | Rint = 0.063 |
Tmin = 0.818, Tmax = 0.866 | 3 standard reflections every 150 reflections |
3054 measured reflections | intensity decay: −0.2% |
2939 independent reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.138 | All H-atom parameters refined |
S = 1.02 | Δρmax = 0.42 e Å−3 |
2939 reflections | Δρmin = −0.41 e Å−3 |
244 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 | ||
C1 | 0.26617 (19) | 0.3923 (2) | 0.30413 (12) | 0.0546 (6) | |
C2 | 0.2226 (2) | 0.4370 (3) | 0.24296 (13) | 0.0658 (7) | |
C3 | 0.2689 (2) | 0.5320 (3) | 0.21345 (13) | 0.0682 (7) | |
C4 | 0.3572 (2) | 0.5819 (3) | 0.24543 (14) | 0.0693 (7) | |
C5 | 0.4015 (2) | 0.5378 (3) | 0.30733 (13) | 0.0603 (6) | |
C6 | 0.35743 (16) | 0.4406 (2) | 0.33671 (10) | 0.0466 (5) | |
C7 | 0.40657 (17) | 0.3943 (2) | 0.40144 (11) | 0.0507 (5) | |
C8 | 0.38053 (17) | 0.2928 (2) | 0.43204 (11) | 0.0484 (5) | |
C9 | 0.43674 (15) | 0.2573 (2) | 0.49674 (10) | 0.0475 (5) | |
C10 | 0.31568 (14) | 0.0741 (2) | 0.50998 (10) | 0.0431 (5) | |
C11 | 0.32167 (14) | −0.0350 (2) | 0.55608 (10) | 0.0445 (5) | |
C12 | 0.40780 (15) | −0.0377 (2) | 0.60323 (10) | 0.0449 (5) | |
C13 | 0.4284 (2) | −0.1325 (3) | 0.65031 (13) | 0.0609 (6) | |
C14 | 0.3570 (3) | −0.2261 (3) | 0.64872 (16) | 0.0751 (8) | |
C15 | 0.2690 (2) | −0.2235 (3) | 0.60270 (16) | 0.0721 (8) | |
C16 | 0.25029 (19) | −0.1287 (3) | 0.55589 (13) | 0.0577 (6) | |
N1 | 0.40356 (12) | 0.14856 (17) | 0.52802 (8) | 0.0431 (4) | |
O1 | 0.51134 (13) | 0.30976 (18) | 0.52541 (9) | 0.0681 (5) | |
O2 | 0.57451 (11) | 0.05719 (17) | 0.58034 (8) | 0.0556 (4) | |
O3 | 0.48326 (13) | 0.17949 (16) | 0.65004 (7) | 0.0591 (4) | |
O4 | 0.24855 (11) | 0.09728 (17) | 0.46506 (8) | 0.0560 (4) | |
S1 | 0.48233 (3) | 0.09468 (5) | 0.59656 (2) | 0.0420 (2) | |
H1 | 0.2345 (18) | 0.328 (3) | 0.3242 (12) | 0.056 (7)* | |
H2 | 0.161 (2) | 0.402 (3) | 0.2207 (14) | 0.079 (9)* | |
H3 | 0.231 (2) | 0.561 (3) | 0.1697 (16) | 0.082 (9)* | |
H4 | 0.391 (2) | 0.643 (3) | 0.2260 (15) | 0.085 (9)* | |
H5 | 0.464 (2) | 0.578 (3) | 0.3293 (13) | 0.065 (8)* | |
H7 | 0.466 (2) | 0.436 (3) | 0.4227 (13) | 0.065 (7)* | |
H8 | 0.324 (2) | 0.249 (3) | 0.4144 (13) | 0.070 (8)* | |
H13 | 0.491 (2) | −0.135 (3) | 0.6826 (14) | 0.072 (8)* | |
H14 | 0.368 (2) | −0.292 (3) | 0.6779 (14) | 0.080 (9)* | |
H15 | 0.223 (2) | −0.289 (3) | 0.6015 (13) | 0.073 (8)* | |
H16 | 0.1909 (19) | −0.123 (2) | 0.5242 (12) | 0.049 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0600 (13) | 0.0547 (13) | 0.0469 (13) | −0.0076 (11) | 0.0049 (10) | 0.0005 (11) |
C2 | 0.0740 (17) | 0.0631 (16) | 0.0536 (15) | 0.0006 (13) | −0.0038 (13) | −0.0013 (12) |
C3 | 0.0870 (19) | 0.0669 (16) | 0.0496 (14) | 0.0176 (15) | 0.0103 (13) | 0.0097 (12) |
C4 | 0.0805 (19) | 0.0644 (16) | 0.0679 (17) | 0.0078 (14) | 0.0266 (15) | 0.0212 (14) |
C5 | 0.0589 (14) | 0.0587 (15) | 0.0642 (15) | −0.0034 (11) | 0.0143 (11) | 0.0101 (12) |
C6 | 0.0515 (11) | 0.0457 (11) | 0.0435 (11) | 0.0003 (9) | 0.0113 (9) | −0.0013 (9) |
C7 | 0.0481 (11) | 0.0551 (13) | 0.0471 (12) | −0.0072 (10) | 0.0053 (9) | −0.0017 (10) |
C8 | 0.0483 (11) | 0.0541 (13) | 0.0411 (11) | −0.0070 (10) | 0.0045 (9) | −0.0029 (9) |
C9 | 0.0436 (10) | 0.0521 (12) | 0.0456 (12) | −0.0066 (9) | 0.0064 (9) | 0.0014 (10) |
C10 | 0.0341 (9) | 0.0535 (12) | 0.0429 (11) | −0.0055 (8) | 0.0102 (8) | −0.0094 (9) |
C11 | 0.0395 (9) | 0.0515 (12) | 0.0454 (11) | −0.0074 (9) | 0.0155 (8) | −0.0094 (9) |
C12 | 0.0438 (10) | 0.0503 (12) | 0.0429 (11) | −0.0079 (9) | 0.0142 (8) | −0.0046 (9) |
C13 | 0.0635 (15) | 0.0624 (15) | 0.0568 (15) | −0.0069 (11) | 0.0116 (12) | 0.0089 (12) |
C14 | 0.087 (2) | 0.0637 (17) | 0.079 (2) | −0.0139 (14) | 0.0254 (16) | 0.0179 (15) |
C15 | 0.0765 (18) | 0.0637 (17) | 0.0817 (19) | −0.0268 (14) | 0.0290 (15) | −0.0020 (14) |
C16 | 0.0480 (12) | 0.0640 (15) | 0.0638 (15) | −0.0176 (10) | 0.0173 (11) | −0.0128 (12) |
N1 | 0.0369 (8) | 0.0496 (10) | 0.0406 (9) | −0.0075 (7) | 0.0025 (6) | −0.0012 (7) |
O1 | 0.0573 (10) | 0.0748 (12) | 0.0632 (10) | −0.0269 (9) | −0.0097 (8) | 0.0155 (9) |
O2 | 0.0372 (7) | 0.0701 (10) | 0.0593 (9) | −0.0014 (7) | 0.0092 (6) | 0.0043 (8) |
O3 | 0.0679 (10) | 0.0627 (10) | 0.0446 (9) | −0.0119 (8) | 0.0056 (7) | −0.0133 (7) |
O4 | 0.0361 (7) | 0.0768 (11) | 0.0512 (9) | −0.0074 (7) | −0.0006 (6) | −0.0020 (8) |
S1 | 0.0370 (3) | 0.0496 (3) | 0.0380 (3) | −0.00695 (19) | 0.00377 (19) | −0.0023 (2) |
C1—C2 | 1.376 (4) | C10—O4 | 1.200 (2) |
C1—C6 | 1.395 (3) | C10—N1 | 1.422 (2) |
C1—H1 | 0.94 (3) | C10—C11 | 1.482 (3) |
C2—C3 | 1.385 (4) | C11—C12 | 1.378 (3) |
C2—H2 | 0.95 (3) | C11—C16 | 1.384 (3) |
C3—C4 | 1.366 (4) | C12—C13 | 1.383 (3) |
C3—H3 | 1.00 (3) | C12—S1 | 1.742 (2) |
C4—C5 | 1.388 (4) | C13—C14 | 1.381 (4) |
C4—H4 | 0.92 (3) | C13—H13 | 0.98 (3) |
C5—C6 | 1.384 (3) | C14—C15 | 1.385 (5) |
C5—H5 | 0.98 (3) | C14—H14 | 0.91 (3) |
C6—C7 | 1.463 (3) | C15—C16 | 1.377 (4) |
C7—C8 | 1.322 (3) | C15—H15 | 0.92 (3) |
C7—H7 | 0.95 (3) | C16—H16 | 0.94 (2) |
C8—C9 | 1.460 (3) | N1—S1 | 1.705 (2) |
C8—H8 | 0.91 (3) | O2—S1 | 1.426 (2) |
C9—O1 | 1.209 (3) | O3—S1 | 1.420 (2) |
C9—N1 | 1.428 (3) | ||
C2—C1—C6 | 120.6 (2) | N1—C10—C11 | 108.4 (2) |
C2—C1—H1 | 119.9 (15) | C12—C11—C16 | 119.6 (2) |
C6—C1—H1 | 119.5 (15) | C12—C11—C10 | 113.93 (17) |
C1—C2—C3 | 120.0 (3) | C16—C11—C10 | 126.4 (2) |
C1—C2—H2 | 120.1 (18) | C11—C12—C13 | 123.0 (2) |
C3—C2—H2 | 119.9 (18) | C11—C12—S1 | 111.2 (2) |
C4—C3—C2 | 119.9 (3) | C13—C12—S1 | 125.8 (2) |
C4—C3—H3 | 125.3 (19) | C14—C13—C12 | 116.5 (3) |
C2—C3—H3 | 114.8 (19) | C14—C13—H13 | 121.4 (18) |
C3—C4—C5 | 120.5 (3) | C12—C13—H13 | 122.1 (18) |
C3—C4—H4 | 121 (2) | C13—C14—C15 | 121.4 (3) |
C5—C4—H4 | 118 (2) | C13—C14—H14 | 120 (2) |
C6—C5—C4 | 120.2 (3) | C15—C14—H14 | 119 (2) |
C6—C5—H5 | 121.6 (16) | C16—C15—C14 | 121.2 (3) |
C4—C5—H5 | 118.2 (16) | C16—C15—H15 | 118.7 (18) |
C5—C6—C1 | 118.7 (2) | C14—C15—H15 | 120.0 (18) |
C5—C6—C7 | 119.1 (2) | C15—C16—C11 | 118.3 (2) |
C1—C6—C7 | 122.2 (2) | C15—C16—H16 | 123.4 (15) |
C8—C7—C6 | 126.1 (2) | C11—C16—H16 | 118.3 (15) |
C8—C7—H7 | 115.8 (16) | C10—N1—C9 | 130.2 (2) |
C6—C7—H7 | 117.9 (16) | C10—N1—S1 | 113.8 (1) |
C7—C8—C9 | 120.2 (2) | C9—N1—S1 | 115.9 (1) |
C7—C8—H8 | 120.0 (18) | O3—S1—O2 | 119.0 (1) |
C9—C8—H8 | 119.5 (18) | O3—S1—N1 | 110.7 (1) |
O1—C9—N1 | 116.8 (2) | O2—S1—N1 | 109.79 (9) |
O1—C9—C8 | 125.5 (2) | O3—S1—C12 | 110.4 (1) |
N1—C9—C8 | 117.6 (2) | O2—S1—C12 | 111.2 (1) |
O4—C10—N1 | 125.1 (2) | N1—S1—C12 | 92.51 (9) |
O4—C10—C11 | 126.5 (2) | ||
C6—C1—C2—C3 | −0.7 (4) | C13—C14—C15—C16 | 1.3 (5) |
C1—C2—C3—C4 | −0.6 (4) | C14—C15—C16—C11 | −0.4 (4) |
C2—C3—C4—C5 | 0.2 (4) | C12—C11—C16—C15 | −1.1 (4) |
C3—C4—C5—C6 | 1.4 (4) | C10—C11—C16—C15 | 179.8 (2) |
C4—C5—C6—C1 | −2.7 (4) | O4—C10—N1—C9 | −5.2 (4) |
C4—C5—C6—C7 | 178.8 (2) | C11—C10—N1—C9 | 175.1 (2) |
C2—C1—C6—C5 | 2.3 (4) | O4—C10—N1—S1 | 177.03 (17) |
C2—C1—C6—C7 | −179.2 (2) | C11—C10—N1—S1 | −2.7 (2) |
C5—C6—C7—C8 | −171.2 (2) | O1—C9—N1—C10 | 174.1 (2) |
C1—C6—C7—C8 | 10.4 (4) | C8—C9—N1—C10 | −8.3 (3) |
C6—C7—C8—C9 | 179.9 (2) | O1—C9—N1—S1 | −8.2 (3) |
C7—C8—C9—O1 | −4.1 (4) | C8—C9—N1—S1 | 169.44 (16) |
C7—C8—C9—N1 | 178.5 (2) | C10—N1—S1—O3 | −109.24 (16) |
O4—C10—C11—C12 | −179.9 (2) | C9—N1—S1—O3 | 72.67 (18) |
N1—C10—C11—C12 | −0.2 (2) | C10—N1—S1—O2 | 117.33 (15) |
O4—C10—C11—C16 | −0.8 (4) | C9—N1—S1—O2 | −60.75 (18) |
N1—C10—C11—C16 | 178.9 (2) | C10—N1—S1—C12 | 3.72 (16) |
C16—C11—C12—C13 | 1.7 (3) | C9—N1—S1—C12 | −174.37 (16) |
C10—C11—C12—C13 | −179.1 (2) | C11—C12—S1—O3 | 109.52 (16) |
C16—C11—C12—S1 | −176.33 (17) | C13—C12—S1—O3 | −68.5 (2) |
C10—C11—C12—S1 | 2.8 (2) | C11—C12—S1—O2 | −116.08 (16) |
C11—C12—C13—C14 | −0.8 (4) | C13—C12—S1—O2 | 65.9 (2) |
S1—C12—C13—C14 | 177.0 (2) | C11—C12—S1—N1 | −3.72 (16) |
C12—C13—C14—C15 | −0.8 (4) | C13—C12—S1—N1 | 178.3 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···O1 | 0.95 (3) | 2.49 (3) | 2.832 (3) | 101.4 (18) |
C8—H8···O4 | 0.91 (3) | 2.26 (3) | 2.901 (3) | 127 (2) |
C15—H15···O2i | 0.92 (3) | 2.57 (3) | 3.478 (3) | 169 (2) |
C16—H16···O1i | 0.94 (2) | 2.56 (3) | 3.277 (3) | 132.6 (18) |
C14—H14···CgAii | 0.91 (3) | 3.07 (3) | 3.916 (4) | 156 (2) |
Symmetry codes: (i) x−1/2, y−1/2, z; (ii) x, −y, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C16H11NO4S |
Mr | 313.32 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 293 |
a, b, c (Å) | 13.714 (3), 10.456 (4), 20.781 (3) |
β (°) | 101.365 (5) |
V (Å3) | 2921.4 (14) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.24 |
Crystal size (mm) | 0.75 × 0.65 × 0.50 |
Data collection | |
Diffractometer | Rigaku AFC-7S diffractometer |
Absorption correction | For a sphere (Dwiggins, 1975) |
Tmin, Tmax | 0.818, 0.866 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3054, 2939, 2325 |
Rint | 0.063 |
(sin θ/λ)max (Å−1) | 0.704 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.138, 1.02 |
No. of reflections | 2939 |
No. of parameters | 244 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.42, −0.41 |
Computer programs: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1994), MSC/AFC Diffractometer Control Software, TEXSAN for Windows (Molecular Structure Corporation, 1997), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2000), WinGX (Farrugia, 1999).
C9—O1 | 1.209 (3) | C12—S1 | 1.742 (2) |
C9—N1 | 1.428 (3) | N1—S1 | 1.705 (2) |
C10—O4 | 1.200 (2) | O2—S1 | 1.426 (2) |
C10—N1 | 1.422 (2) | O3—S1 | 1.420 (2) |
C8—C7—C6 | 126.1 (2) | C10—N1—C9 | 130.2 (2) |
C7—C8—C9 | 120.2 (2) | C10—N1—S1 | 113.8 (1) |
O1—C9—N1 | 116.8 (2) | C9—N1—S1 | 115.9 (1) |
O1—C9—C8 | 125.5 (2) | O3—S1—O2 | 119.0 (1) |
N1—C9—C8 | 117.6 (2) | O3—S1—N1 | 110.7 (1) |
O4—C10—N1 | 125.1 (2) | O2—S1—N1 | 109.79 (9) |
O4—C10—C11 | 126.5 (2) | O3—S1—C12 | 110.4 (1) |
N1—C10—C11 | 108.4 (2) | O2—S1—C12 | 111.2 (1) |
C11—C12—S1 | 111.2 (2) | N1—S1—C12 | 92.51 (9) |
C13—C12—S1 | 125.8 (2) | ||
C5—C6—C7—C8 | −171.2 (2) | O4—C10—N1—C9 | −5.2 (4) |
C6—C7—C8—C9 | 179.9 (2) | C8—C9—N1—C10 | −8.3 (3) |
C7—C8—C9—N1 | 178.5 (2) | O1—C9—N1—S1 | −8.2 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
C7—H7···O1 | 0.95 (3) | 2.49 (3) | 2.832 (3) | 101.4 (18) |
C8—H8···O4 | 0.91 (3) | 2.26 (3) | 2.901 (3) | 127 (2) |
C15—H15···O2i | 0.92 (3) | 2.57 (3) | 3.478 (3) | 169 (2) |
C16—H16···O1i | 0.94 (2) | 2.56 (3) | 3.277 (3) | 132.6 (18) |
C14—H14···CgAii | 0.91 (3) | 3.07 (3) | 3.916 (4) | 156 (2) |
Symmetry codes: (i) x−1/2, y−1/2, z; (ii) x, −y, z+1/2. |
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Derivatives of saccharin are known for their biological activity (Strupczewski et al., 1995). The saccharyl system has also been used as a cheap and effective leaving group in important chemical transformations, such as the derivatization of phenols prior to their conversion into arenes by transfer hydrogenolysis (Brigas & Johnstone, 1990). Cinnamic acid derivatives show antibacterial, antifungal (Takeichi, 1962) and antioxidant activities (Natella et al., 1999). Cinnamic acids with substitutions on the phenyl ring showing antibacterial and antimicrobial activities have also been reported (Ramanan & Rao, 1987). Taking into account these important features of the saccharin and cinnamoyl groups, we have undertaken the X-ray diffraction study of the title compound, (I), in order to understand the molecular features which stabilize its observed conformation.
A view of (I) with the atom-labelling scheme is shown in Fig. 1. The saccharin group (C10/C11–C16/N1/S1/O4) is planar to within 0.0526 (2) Å, and the two sulfone O atoms (O2 and O3) lie approximately 1.23 Å above and below this plane. The crystal structure of (I) can be described as being built from essentially planar fragments, viz. a three-atom bridge (C7/C8/C9) linking the aromatic ring (C1–C6) with the saccharin group. The dihedral angle between the saccharin group and the aromatic ring (C1–C6) is 13.3 (2)°. Two intramolecular C—H···O hydrogen-bond-like contacts (Fig. 1 and Table 2) may contribute to the stability of this conformation. The small C12—S1—N1 angle of 92.51 (9)° in the five-membered ring, similar to the value of 92.7 (1)° found in saccharin itself (Bart, 1968), results from a compromise with ring strain, and makes it possible for the whole saccharin group to become quite planar.
There are two intermolecular C—H···O contacts in the structure of (I) (Table 2). The supramolecular aggregation is determined by two almost equal C—H···O hydrogen bonds. In these two interactions, aromatic atom C16 in the molecule at (x, y, z) acts as a hydrogen-bond donor to carbonyl atom O1 in the molecule at (x + 1/2, y − 1/2, z) and aromatic atom C15 in the molecule at (x, y, z) acts as a hydrogen-bond donor to sulfoxide atom O2 in the molecule at (x + 1/2, y − 1/2, z). Because of these interactions, molecules of (I) are arranged so that C—H···O hydrogen bonds form an S(5)S(6)[R22(9)]S(5)S(6) motif (Bernstein et al., 1995) (Fig 2).
In the extended structure of (I), there is a weak C—H···π intermolecular interaction involving C14—H14 with the centroid [CgA] of ring A (C1–C6) of the molecule at (x,-y,1/2 + z); see Table 2 for details. This varied set of hydrogen-bonding and π···ring interactions contributes to the stabilization of the crystal structure (Fig. 3).