2-[(E)-(Dimethyl­amino)methyl­eneamino]-N-phenyl­benzene­sulfonamide

In the title compound, C₁₅H₁₇N₃O₂S, all bond lengths and angles are normal. Intra­molecular N—H...N hydrogen bonding influences the mol­ecular conformation. The benzene and phenyl rings make a dihedral angle of 75.80 (2)°. In the crystal structure, weak inter­molecular C—H...O hydrogen bonds link the mol­ecules into zigzag chains extended along the b axis.

Key indicators

• Single-crystal X-ray study
• T = 153 K
• Mean [sigma](C-C)= 0.002 Å
• R factor = 0.032
• wR factor = 0.082
• Data-to-parameter ratio = 13.2

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S1. Comment

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.

Related literature

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).

S2. Experimental

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.

S3. Refinement

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 U_iso(H)= 1.2–1.5Ueq(C). Atom H1A was refined isotropically.

Computing details

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).

Figures

Fig. 1. The molecular structure of (I), with the atom labels and 40% probability displacement ellipsoids.

2-[(E)-(Dimethylamino)methyleneamino]-N-phenylbenzenesulfonamide

Crystal data

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) Å^3	0.47 × 0.43 × 0.20 mm
Z = 8

Data collection

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

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.082	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0399P)^2 + 3.4264P] where P = (Fo^2 + 2Fc^2)/3
2583 reflections	(Δ/σ)max < 0.001
196 parameters	Δρmax = 0.21 e Å^−3
0 restraints	Δρmin = −0.44 e Å^−3

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	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)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

Geometric parameters (Å, º)

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)

Hydrogen-bond geometry (Å, º)

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···O1^i	0.95	2.47	3.2724 (19)	143

Symmetry code: (i) −x+1/2, y−1/2, −z+1/2.