Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807050040/cv2317sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807050040/cv2317Isup2.hkl |
CCDC reference: 667450
2-Amino-N-phenyl-benzenesulfonamide (10 mmol) was added dropwise to the solution of NaOH (25 mmol)in DMF(20 ml) and the mixture was heated under reflux for 2 h. Then the mixture was poured into water and extracted with CH2Cl2 (35 ml) and the organic layer was washed with 10% NaCl solution and water. The excess CH2Cl2 was removed on a water vacuum pump to obtain the final product (80% yield). Single crystals suitable for X-ray measurements were obtained by recrystallization from methanol at room temperature.
All H atoms were found on difference maps. C-bound H atoms were placed in idealized positions (C—H 0.95–0.98 Å) and refined as riding, with Uiso(H)= 1.2–1.5Ueq(C). Atom H1A was refined isotropically.
Sulfonimide is an important kind of group in organic chemistry. Many compounds containing sulfonimide groups possess a broad spectrum of biological activities and can be widely used as herbicides (Kamoshita et al., 1987). In addition, some compounds containing sulfonimide groups can be used as catalyst (Zhang et al., 2007). Here, we report the crystal structure of (I).
In (I) (Fig. 1), all bond lengths and angles are normal and in a good agreement with those reported previously (Henschel et al., 1996). The two rings - C4—C9 and C10—C15 - are oriented at angle of 75.80 (2)°. The intramolecular N1—H1A···N2 hydrogen bond influences the molecular conformation. In the crystal, the weak intermolecular C—H···O hydrogen bonds link the molecules into zigzag chains extended along the b axis.
For a related crystal structure, see: Henschel et al. (1996). For applications of sulfonimide derivatives, see: Kamoshita et al. (1987) and Zhang et al. (2007).
Data collection: RAPID-AUTO (Rigaku, 2004); cell refinement: RAPID-AUTO (Rigaku, 2004); data reduction: RAPID-AUTO (Rigaku, 2004); program(s) used to solve structure: SHELXTL (Sheldrick, 2001); program(s) used to refine structure: SHELXTL (Sheldrick, 2001); molecular graphics: SHELXTL (Sheldrick, 2001); software used to prepare material for publication: SHELXTL (Sheldrick, 2001).
Fig. 1. The molecular structure of (I), with the atom labels and 40% probability displacement ellipsoids. |
C15H17N3O2S | F(000) = 1280 |
Mr = 303.38 | Dx = 1.371 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 4407 reflections |
a = 16.297 (3) Å | θ = 2.9–26.4° |
b = 8.9962 (18) Å | µ = 0.23 mm−1 |
c = 20.314 (4) Å | T = 153 K |
β = 99.28 (3)° | Block, colourless |
V = 2939.3 (10) Å3 | 0.47 × 0.43 × 0.20 mm |
Z = 8 |
Rigaku R0AXIS RAPID IP area-detector diffractometer | 2583 independent reflections |
Radiation source: Rotating Anode | 2470 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.014 |
ω scans | θmax = 25.0°, θmin = 3.2° |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | h = −19→19 |
Tmin = 0.901, Tmax = 0.956 | k = −10→10 |
11196 measured reflections | l = −24→24 |
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)] = 0.032 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.082 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0399P)2 + 3.4264P] where P = (Fo2 + 2Fc2)/3 |
2583 reflections | (Δ/σ)max < 0.001 |
196 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.44 e Å−3 |
C15H17N3O2S | V = 2939.3 (10) Å3 |
Mr = 303.38 | Z = 8 |
Monoclinic, C2/c | Mo Kα radiation |
a = 16.297 (3) Å | µ = 0.23 mm−1 |
b = 8.9962 (18) Å | T = 153 K |
c = 20.314 (4) Å | 0.47 × 0.43 × 0.20 mm |
β = 99.28 (3)° |
Rigaku R0AXIS RAPID IP area-detector diffractometer | 2583 independent reflections |
Absorption correction: multi-scan (ABSCOR; Higashi, 1995) | 2470 reflections with I > 2σ(I) |
Tmin = 0.901, Tmax = 0.956 | Rint = 0.014 |
11196 measured reflections |
R[F2 > 2σ(F2)] = 0.032 | 0 restraints |
wR(F2) = 0.082 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.07 | Δρmax = 0.21 e Å−3 |
2583 reflections | Δρmin = −0.44 e Å−3 |
196 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 | ||
S1 | 0.15973 (2) | 0.20300 (4) | 0.133242 (16) | 0.02004 (12) | |
O1 | 0.12393 (7) | 0.31020 (12) | 0.17211 (5) | 0.0288 (3) | |
O2 | 0.15721 (7) | 0.22993 (12) | 0.06340 (5) | 0.0269 (3) | |
N1 | 0.25745 (8) | 0.18718 (14) | 0.16876 (6) | 0.0220 (3) | |
N2 | 0.16787 (7) | 0.03356 (13) | 0.26003 (6) | 0.0193 (3) | |
C3 | 0.14768 (9) | 0.01258 (16) | 0.31854 (7) | 0.0198 (3) | |
H3A | 0.0980 | −0.0405 | 0.3216 | 0.024* | |
C1 | 0.16694 (11) | 0.0447 (2) | 0.43857 (7) | 0.0313 (4) | |
H1C | 0.1143 | −0.0100 | 0.4331 | 0.047* | |
H1D | 0.1593 | 0.1429 | 0.4576 | 0.047* | |
H1E | 0.2094 | −0.0105 | 0.4686 | 0.047* | |
C11 | 0.35427 (9) | −0.02078 (17) | 0.18347 (7) | 0.0261 (3) | |
H11A | 0.3415 | −0.0350 | 0.2271 | 0.031* | |
C13 | 0.43044 (10) | −0.09194 (19) | 0.09645 (8) | 0.0319 (4) | |
H13A | 0.4703 | −0.1539 | 0.0807 | 0.038* | |
C2 | 0.27188 (10) | 0.13687 (19) | 0.37240 (8) | 0.0289 (4) | |
H2C | 0.3060 | 0.0764 | 0.3471 | 0.043* | |
H2D | 0.3013 | 0.1507 | 0.4180 | 0.043* | |
H2E | 0.2614 | 0.2340 | 0.3508 | 0.043* | |
C14 | 0.38898 (9) | 0.01647 (19) | 0.05553 (8) | 0.0274 (3) | |
H14A | 0.4000 | 0.0275 | 0.0113 | 0.033* | |
C6 | 0.04005 (9) | −0.24517 (18) | 0.15244 (8) | 0.0248 (3) | |
H6A | 0.0144 | −0.3389 | 0.1563 | 0.030* | |
C4 | 0.12052 (8) | −0.03763 (16) | 0.20566 (7) | 0.0183 (3) | |
C15 | 0.33173 (9) | 0.10892 (17) | 0.07828 (7) | 0.0226 (3) | |
H15A | 0.3050 | 0.1852 | 0.0504 | 0.027* | |
C10 | 0.31362 (9) | 0.08928 (16) | 0.14230 (7) | 0.0206 (3) | |
C12 | 0.41316 (10) | −0.10926 (18) | 0.16082 (8) | 0.0317 (4) | |
H12A | 0.4420 | −0.1823 | 0.1894 | 0.038* | |
C7 | 0.03399 (9) | −0.17763 (18) | 0.09029 (8) | 0.0265 (3) | |
H7A | 0.0043 | −0.2245 | 0.0518 | 0.032* | |
C8 | 0.07166 (9) | −0.04144 (18) | 0.08525 (7) | 0.0223 (3) | |
H8A | 0.0688 | 0.0049 | 0.0429 | 0.027* | |
N3 | 0.19335 (8) | 0.06204 (14) | 0.37424 (6) | 0.0217 (3) | |
C5 | 0.08311 (9) | −0.17730 (16) | 0.20879 (7) | 0.0212 (3) | |
H5A | 0.0874 | −0.2265 | 0.2506 | 0.025* | |
C9 | 0.11380 (8) | 0.02794 (16) | 0.14199 (7) | 0.0183 (3) | |
H1A | 0.2568 (12) | 0.168 (2) | 0.2103 (10) | 0.034 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0241 (2) | 0.0200 (2) | 0.0155 (2) | 0.00066 (14) | 0.00152 (14) | 0.00187 (13) |
O1 | 0.0367 (6) | 0.0235 (6) | 0.0263 (6) | 0.0051 (5) | 0.0050 (5) | −0.0020 (4) |
O2 | 0.0321 (6) | 0.0304 (6) | 0.0173 (5) | 0.0008 (5) | 0.0016 (4) | 0.0070 (4) |
N1 | 0.0236 (7) | 0.0263 (7) | 0.0153 (6) | −0.0056 (5) | 0.0012 (5) | 0.0005 (5) |
N2 | 0.0205 (6) | 0.0221 (6) | 0.0147 (6) | −0.0008 (5) | 0.0013 (5) | 0.0011 (5) |
C3 | 0.0193 (7) | 0.0201 (7) | 0.0198 (7) | −0.0008 (6) | 0.0028 (6) | 0.0024 (6) |
C1 | 0.0368 (9) | 0.0412 (10) | 0.0161 (7) | −0.0076 (7) | 0.0049 (6) | 0.0016 (7) |
C11 | 0.0286 (8) | 0.0257 (8) | 0.0223 (7) | −0.0077 (6) | −0.0013 (6) | 0.0060 (6) |
C13 | 0.0271 (8) | 0.0293 (9) | 0.0376 (9) | 0.0000 (7) | 0.0006 (7) | −0.0067 (7) |
C2 | 0.0265 (8) | 0.0352 (9) | 0.0242 (8) | −0.0098 (7) | 0.0016 (6) | −0.0012 (7) |
C14 | 0.0256 (8) | 0.0340 (9) | 0.0221 (7) | −0.0052 (7) | 0.0019 (6) | −0.0038 (6) |
C6 | 0.0192 (7) | 0.0247 (8) | 0.0316 (8) | −0.0031 (6) | 0.0070 (6) | −0.0048 (6) |
C4 | 0.0144 (6) | 0.0225 (7) | 0.0181 (7) | 0.0019 (6) | 0.0032 (5) | −0.0011 (6) |
C15 | 0.0223 (7) | 0.0249 (8) | 0.0192 (7) | −0.0048 (6) | −0.0007 (5) | 0.0031 (6) |
C10 | 0.0200 (7) | 0.0207 (7) | 0.0200 (7) | −0.0078 (6) | −0.0004 (5) | −0.0001 (6) |
C12 | 0.0316 (9) | 0.0237 (8) | 0.0362 (9) | −0.0020 (7) | −0.0051 (7) | 0.0051 (7) |
C7 | 0.0204 (7) | 0.0343 (9) | 0.0244 (8) | −0.0028 (6) | 0.0021 (6) | −0.0102 (7) |
C8 | 0.0181 (7) | 0.0315 (8) | 0.0171 (7) | 0.0018 (6) | 0.0020 (5) | −0.0024 (6) |
N3 | 0.0236 (6) | 0.0264 (7) | 0.0151 (6) | −0.0047 (5) | 0.0029 (5) | 0.0011 (5) |
C5 | 0.0180 (7) | 0.0238 (7) | 0.0227 (7) | 0.0012 (6) | 0.0059 (6) | 0.0013 (6) |
C9 | 0.0156 (6) | 0.0216 (7) | 0.0177 (7) | 0.0013 (5) | 0.0030 (5) | −0.0004 (5) |
S1—O1 | 1.4291 (12) | C2—N3 | 1.4519 (19) |
S1—O2 | 1.4332 (11) | C2—H2C | 0.9800 |
S1—N1 | 1.6451 (13) | C2—H2D | 0.9800 |
S1—C9 | 1.7650 (15) | C2—H2E | 0.9800 |
N1—C10 | 1.436 (2) | C14—C15 | 1.384 (2) |
N1—H1A | 0.86 (2) | C14—H14A | 0.9500 |
N2—C3 | 1.2972 (18) | C6—C5 | 1.384 (2) |
N2—C4 | 1.3965 (18) | C6—C7 | 1.390 (2) |
C3—N3 | 1.3270 (19) | C6—H6A | 0.9500 |
C3—H3A | 0.9500 | C4—C5 | 1.403 (2) |
C1—N3 | 1.4487 (18) | C4—C9 | 1.410 (2) |
C1—H1C | 0.9800 | C15—C10 | 1.390 (2) |
C1—H1D | 0.9800 | C15—H15A | 0.9500 |
C1—H1E | 0.9800 | C12—H12A | 0.9500 |
C11—C12 | 1.382 (2) | C7—C8 | 1.382 (2) |
C11—C10 | 1.393 (2) | C7—H7A | 0.9500 |
C11—H11A | 0.9500 | C8—C9 | 1.391 (2) |
C13—C14 | 1.385 (2) | C8—H8A | 0.9500 |
C13—C12 | 1.390 (2) | C5—H5A | 0.9500 |
C13—H13A | 0.9500 | ||
O1—S1—O2 | 118.93 (7) | C15—C14—H14A | 119.6 |
O1—S1—N1 | 105.58 (7) | C13—C14—H14A | 119.6 |
O2—S1—N1 | 108.65 (7) | C5—C6—C7 | 120.70 (14) |
O1—S1—C9 | 109.20 (7) | C5—C6—H6A | 119.7 |
O2—S1—C9 | 107.80 (7) | C7—C6—H6A | 119.7 |
N1—S1—C9 | 105.96 (6) | N2—C4—C5 | 124.31 (13) |
C10—N1—S1 | 121.29 (10) | N2—C4—C9 | 119.01 (13) |
C10—N1—H1A | 110.7 (13) | C5—C4—C9 | 116.52 (13) |
S1—N1—H1A | 106.4 (13) | C14—C15—C10 | 119.49 (14) |
C3—N2—C4 | 117.93 (12) | C14—C15—H15A | 120.3 |
N2—C3—N3 | 122.84 (13) | C10—C15—H15A | 120.3 |
N2—C3—H3A | 118.6 | C15—C10—C11 | 119.99 (14) |
N3—C3—H3A | 118.6 | C15—C10—N1 | 121.10 (13) |
N3—C1—H1C | 109.5 | C11—C10—N1 | 118.77 (13) |
N3—C1—H1D | 109.5 | C11—C12—C13 | 120.38 (15) |
H1C—C1—H1D | 109.5 | C11—C12—H12A | 119.8 |
N3—C1—H1E | 109.5 | C13—C12—H12A | 119.8 |
H1C—C1—H1E | 109.5 | C8—C7—C6 | 119.18 (14) |
H1D—C1—H1E | 109.5 | C8—C7—H7A | 120.4 |
C12—C11—C10 | 119.87 (14) | C6—C7—H7A | 120.4 |
C12—C11—H11A | 120.1 | C7—C8—C9 | 120.16 (14) |
C10—C11—H11A | 120.1 | C7—C8—H8A | 119.9 |
C14—C13—C12 | 119.37 (15) | C9—C8—H8A | 119.9 |
C14—C13—H13A | 120.3 | C3—N3—C1 | 121.72 (13) |
C12—C13—H13A | 120.3 | C3—N3—C2 | 120.60 (12) |
N3—C2—H2C | 109.5 | C1—N3—C2 | 117.68 (12) |
N3—C2—H2D | 109.5 | C6—C5—C4 | 121.58 (14) |
H2C—C2—H2D | 109.5 | C6—C5—H5A | 119.2 |
N3—C2—H2E | 109.5 | C4—C5—H5A | 119.2 |
H2C—C2—H2E | 109.5 | C8—C9—C4 | 121.84 (14) |
H2D—C2—H2E | 109.5 | C8—C9—S1 | 118.53 (11) |
C15—C14—C13 | 120.85 (15) | C4—C9—S1 | 119.63 (11) |
O1—S1—N1—C10 | −179.13 (11) | N2—C3—N3—C1 | 176.32 (14) |
O2—S1—N1—C10 | −50.50 (13) | N2—C3—N3—C2 | −3.2 (2) |
C9—S1—N1—C10 | 65.09 (12) | C7—C6—C5—C4 | 1.3 (2) |
C4—N2—C3—N3 | 172.83 (13) | N2—C4—C5—C6 | −176.99 (13) |
C12—C13—C14—C15 | 1.0 (2) | C9—C4—C5—C6 | −1.6 (2) |
C3—N2—C4—C5 | −32.9 (2) | C7—C8—C9—C4 | 0.8 (2) |
C3—N2—C4—C9 | 151.77 (13) | C7—C8—C9—S1 | −179.14 (11) |
C13—C14—C15—C10 | −2.2 (2) | N2—C4—C9—C8 | 176.20 (13) |
C14—C15—C10—C11 | 1.3 (2) | C5—C4—C9—C8 | 0.5 (2) |
C14—C15—C10—N1 | 177.14 (13) | N2—C4—C9—S1 | −3.85 (18) |
C12—C11—C10—C15 | 0.7 (2) | C5—C4—C9—S1 | −179.51 (10) |
C12—C11—C10—N1 | −175.25 (13) | O1—S1—C9—C8 | 119.83 (12) |
S1—N1—C10—C15 | 61.15 (17) | O2—S1—C9—C8 | −10.70 (13) |
S1—N1—C10—C11 | −122.99 (13) | N1—S1—C9—C8 | −126.88 (12) |
C10—C11—C12—C13 | −1.8 (2) | O1—S1—C9—C4 | −60.12 (13) |
C14—C13—C12—C11 | 1.0 (2) | O2—S1—C9—C4 | 169.35 (11) |
C5—C6—C7—C8 | 0.1 (2) | N1—S1—C9—C4 | 53.17 (13) |
C6—C7—C8—C9 | −1.1 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···N2 | 0.86 (2) | 2.249 (19) | 2.8899 (18) | 131.1 (17) |
C11—H11A···O1i | 0.95 | 2.47 | 3.2724 (19) | 143 |
Symmetry code: (i) −x+1/2, y−1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C15H17N3O2S |
Mr | 303.38 |
Crystal system, space group | Monoclinic, C2/c |
Temperature (K) | 153 |
a, b, c (Å) | 16.297 (3), 8.9962 (18), 20.314 (4) |
β (°) | 99.28 (3) |
V (Å3) | 2939.3 (10) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.23 |
Crystal size (mm) | 0.47 × 0.43 × 0.20 |
Data collection | |
Diffractometer | Rigaku R0AXIS RAPID IP area-detector |
Absorption correction | Multi-scan (ABSCOR; Higashi, 1995) |
Tmin, Tmax | 0.901, 0.956 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11196, 2583, 2470 |
Rint | 0.014 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.032, 0.082, 1.07 |
No. of reflections | 2583 |
No. of parameters | 196 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.21, −0.44 |
Computer programs: RAPID-AUTO (Rigaku, 2004), SHELXTL (Sheldrick, 2001).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1A···N2 | 0.86 (2) | 2.249 (19) | 2.8899 (18) | 131.1 (17) |
C11—H11A···O1i | 0.95 | 2.47 | 3.2724 (19) | 142.7 |
Symmetry code: (i) −x+1/2, y−1/2, −z+1/2. |
Sulfonimide is an important kind of group in organic chemistry. Many compounds containing sulfonimide groups possess a broad spectrum of biological activities and can be widely used as herbicides (Kamoshita et al., 1987). In addition, some compounds containing sulfonimide groups can be used as catalyst (Zhang et al., 2007). Here, we report the crystal structure of (I).
In (I) (Fig. 1), all bond lengths and angles are normal and in a good agreement with those reported previously (Henschel et al., 1996). The two rings - C4—C9 and C10—C15 - are oriented at angle of 75.80 (2)°. The intramolecular N1—H1A···N2 hydrogen bond influences the molecular conformation. In the crystal, the weak intermolecular C—H···O hydrogen bonds link the molecules into zigzag chains extended along the b axis.