4-{[4-(Di-methyl-amino)-benzyl-idene]amino}-benzene-sulfonamide.

The title Schiff base compound, C15H17N3O2S, is non-planar with a dihedral angle of 69.88 (4)° between the planes of the benzene rings. In the crystal, pairs of N-H⋯N hydrogen bonds, between the sulfonamide nitro-gen-H atom and the azomethine N atom, link the mol-ecules into inversion dimers, forming R 2 (2)(16) ring motifs. These dimers are linked by N-H⋯O hydrogen bonds, between the sulfonamide nitro-gen-H atom and one sulfonamide O atom, forming sheets lying parallel to (100). Within the sheets there are weak parallel slipped π-π inter-actions involving inversion-related benzene-sulfonamide rings [centroid-centroid distance = 3.8800 (9) Å; normal distance = 3.4796 (6) Å; slippage = 1.717 Å].

Related literature

For the biological and physical properties of sulfonamides and their derivatives and for their pharmacological applications, see: Chohan & Shad (2012 ▶); Domagk (1935 ▶); Khalil et al. (2009 ▶); Sharaby (2007 ▶); Lin et al. (2008 ▶); Maren (1967 ▶); Mohamed et al. (2013 ▶); Saluja et al. (2014 ▶); Supuran et al. (1996 ▶); Türkmen et al. (2005 ▶). For related structures, see: Idemudia et al. (2012 ▶); Loughrey et al. (2009 ▶). For bond-length data, see: Allen et al. (1987 ▶). For graph-set analysis, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C15H17N3O2S

M = 303.38

Monoclinic,

a = 16.8982 (5) Å

b = 9.0273 (3) Å

c = 9.8405 (3) Å

β = 101.552 (3)°

V = 1470.71 (8) Å3

Z = 4

Mo Kα radiation

μ = 0.23 mm−1

T = 296 K

0.35 × 0.22 × 0.15 mm

Data collection

Bruker SMART BREEZE CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2012 ▶) T min = 0.924, T max = 0.987

19398 measured reflections

3644 independent reflections

3133 reflections with I > 2σ(I)

R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.116

S = 1.08

3644 reflections

204 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.29 e Å−3

Data collection: APEX2 (Bruker, 2012 ▶); cell refinement: SAINT (Bruker, 2012 ▶); 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 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: WinGX (Farrugia, 2012 ▶) and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814012136/su2738sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814012136/su2738Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814012136/su2738Isup3.cml

CCDC reference: 1005250

Additional supporting information: crystallographic information; 3D view; checkCIF report

C15H17N3O2S	F(000) = 640
Mr = 303.38	Dx = 1.370 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9899 reflections
a = 16.8982 (5) Å	θ = 2.3–28.3°
b = 9.0273 (3) Å	µ = 0.23 mm−1
c = 9.8405 (3) Å	T = 296 K
β = 101.552 (3)°	Prism, yellow
V = 1470.71 (8) Å3	0.35 × 0.22 × 0.15 mm
Z = 4

Bruker SMART BREEZE CCD diffractometer	3644 independent reflections
Radiation source: fine-focus sealed tube	3133 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.025
φ and ω scans	θmax = 28.3°, θmin = 1.2°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −22→22
Tmin = 0.924, Tmax = 0.987	k = −7→12
19398 measured reflections	l = −11→13

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)] = 0.040	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ2(Fo2) + (0.0572P)2 + 0.485P] where P = (Fo2 + 2Fc2)/3
3644 reflections	(Δ/σ)max = 0.001
204 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.29 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.329465 (19)	0.28756 (4)	0.08578 (4)	0.03754 (13)
O1	0.30989 (7)	0.13297 (14)	0.08516 (15)	0.0608 (4)
O2	0.31107 (7)	0.37779 (18)	0.19404 (13)	0.0613 (4)
N1	1.05511 (8)	0.16049 (17)	0.10070 (15)	0.0479 (3)
N2	0.68218 (7)	0.32679 (14)	0.09636 (13)	0.0364 (3)
N3	0.28201 (7)	0.35422 (17)	−0.05859 (14)	0.0385 (3)
H31	0.2899 (12)	0.441 (3)	−0.069 (2)	0.058 (6)*
H32	0.2864 (13)	0.300 (2)	−0.125 (2)	0.059 (6)*
C1	1.10626 (9)	0.0462 (2)	0.17517 (18)	0.0516 (4)
H1A	1.1559	0.0414	0.1419	0.077*
H1B	1.0791	−0.0476	0.1606	0.077*
H1C	1.1178	0.0690	0.2724	0.077*
C2	1.09209 (11)	0.2638 (2)	0.0203 (2)	0.0611 (5)
H2A	1.1451	0.2294	0.0148	0.092*
H2B	1.0961	0.3593	0.0640	0.092*
H2C	1.0597	0.2714	−0.0715	0.092*
C3	0.97582 (8)	0.17399 (17)	0.10927 (15)	0.0350 (3)
C4	0.92808 (9)	0.29053 (16)	0.04153 (18)	0.0410 (3)
H4	0.9514	0.3603	−0.0079	0.049*
C5	0.84765 (9)	0.30314 (16)	0.04715 (17)	0.0394 (3)
H5	0.8178	0.3817	0.0021	0.047*
C6	0.81000 (8)	0.20063 (16)	0.11890 (15)	0.0347 (3)
C7	0.85645 (9)	0.08345 (18)	0.18336 (16)	0.0405 (3)
H7	0.8321	0.0119	0.2292	0.049*
C8	0.93761 (9)	0.07021 (18)	0.18125 (15)	0.0405 (3)
H8	0.9672	−0.0079	0.2277	0.049*
C9	0.72524 (8)	0.21083 (16)	0.12705 (16)	0.0363 (3)
H9	0.7038 (10)	0.128 (2)	0.1561 (17)	0.041 (4)*
C10	0.59860 (8)	0.31581 (15)	0.09662 (14)	0.0321 (3)
C11	0.55164 (9)	0.20677 (16)	0.01965 (17)	0.0408 (3)
H11	0.5755	0.1385	−0.0305	0.049*
C12	0.46948 (9)	0.19932 (17)	0.01722 (18)	0.0416 (3)
H12	0.4382	0.1260	−0.0340	0.050*
C13	0.43431 (8)	0.30106 (15)	0.09101 (14)	0.0321 (3)
C14	0.47978 (8)	0.41333 (17)	0.16501 (15)	0.0363 (3)
H14	0.4554	0.4829	0.2129	0.044*
C15	0.56207 (8)	0.42089 (17)	0.16691 (15)	0.0372 (3)
H15	0.5928	0.4965	0.2154	0.045*

	U11	U22	U33	U12	U13	U23
S1	0.02420 (17)	0.0491 (2)	0.0407 (2)	0.00001 (13)	0.00964 (14)	0.00972 (15)
O1	0.0358 (6)	0.0526 (7)	0.0930 (10)	−0.0060 (5)	0.0103 (6)	0.0303 (7)
O2	0.0387 (6)	0.1018 (11)	0.0477 (7)	0.0046 (7)	0.0191 (5)	−0.0089 (7)
N1	0.0281 (6)	0.0592 (8)	0.0583 (8)	0.0037 (6)	0.0131 (6)	0.0048 (7)
N2	0.0254 (5)	0.0400 (6)	0.0449 (7)	−0.0016 (5)	0.0095 (5)	0.0025 (5)
N3	0.0281 (6)	0.0441 (7)	0.0425 (7)	0.0011 (5)	0.0055 (5)	0.0067 (6)
C1	0.0308 (7)	0.0734 (12)	0.0487 (9)	0.0107 (7)	0.0030 (6)	−0.0042 (8)
C2	0.0372 (8)	0.0600 (11)	0.0927 (15)	−0.0065 (8)	0.0292 (9)	0.0010 (10)
C3	0.0274 (6)	0.0421 (7)	0.0356 (7)	−0.0013 (5)	0.0069 (5)	−0.0062 (6)
C4	0.0335 (7)	0.0382 (8)	0.0544 (9)	−0.0018 (6)	0.0164 (6)	0.0037 (6)
C5	0.0324 (7)	0.0362 (7)	0.0508 (9)	0.0038 (5)	0.0116 (6)	0.0060 (6)
C6	0.0259 (6)	0.0396 (7)	0.0390 (7)	−0.0001 (5)	0.0073 (5)	−0.0001 (6)
C7	0.0330 (7)	0.0456 (8)	0.0444 (8)	0.0016 (6)	0.0116 (6)	0.0103 (6)
C8	0.0322 (7)	0.0481 (8)	0.0410 (8)	0.0073 (6)	0.0068 (6)	0.0073 (6)
C9	0.0281 (6)	0.0391 (8)	0.0426 (8)	−0.0020 (5)	0.0092 (6)	0.0047 (6)
C10	0.0245 (6)	0.0363 (7)	0.0357 (7)	−0.0003 (5)	0.0066 (5)	0.0051 (5)
C11	0.0306 (7)	0.0387 (8)	0.0541 (9)	0.0017 (5)	0.0110 (6)	−0.0104 (6)
C12	0.0307 (7)	0.0386 (8)	0.0543 (9)	−0.0042 (5)	0.0055 (6)	−0.0099 (6)
C13	0.0241 (6)	0.0385 (7)	0.0340 (7)	0.0007 (5)	0.0067 (5)	0.0051 (5)
C14	0.0319 (7)	0.0419 (7)	0.0368 (7)	0.0011 (6)	0.0111 (5)	−0.0053 (6)
C15	0.0309 (6)	0.0419 (8)	0.0385 (7)	−0.0056 (6)	0.0068 (5)	−0.0073 (6)

S1—O1	1.4340 (13)	C4—H4	0.9300
S1—O2	1.4239 (13)	C5—H5	0.9300
S1—N3	1.6023 (13)	C6—C5	1.393 (2)
S1—C13	1.7664 (13)	C6—C7	1.392 (2)
N1—C1	1.447 (2)	C6—C9	1.4534 (18)
N1—C2	1.444 (2)	C7—C8	1.3809 (19)
N2—C9	1.2762 (19)	C7—H7	0.9300
N2—C10	1.4163 (16)	C8—H8	0.9300
N3—H31	0.81 (2)	C9—H9	0.904 (18)
N3—H32	0.83 (2)	C10—C15	1.389 (2)
C1—H1A	0.9600	C10—C11	1.390 (2)
C1—H1B	0.9600	C11—H11	0.9300
C1—H1C	0.9600	C12—C11	1.385 (2)
C2—H2A	0.9600	C12—H12	0.9300
C2—H2B	0.9600	C13—C12	1.377 (2)
C2—H2C	0.9600	C13—C14	1.3869 (19)
C3—N1	1.3647 (18)	C14—C15	1.3887 (18)
C3—C4	1.409 (2)	C14—H14	0.9300
C3—C8	1.407 (2)	C15—H15	0.9300
C4—C5	1.376 (2)
O2—S1—O1	118.37 (9)	C4—C5—H5	119.3
O1—S1—N3	106.72 (8)	C6—C5—H5	119.3
O1—S1—C13	107.24 (7)	C5—C6—C9	122.76 (13)
O2—S1—N3	107.64 (8)	C7—C6—C5	117.57 (13)
O2—S1—C13	107.86 (7)	C7—C6—C9	119.67 (13)
N3—S1—C13	108.72 (7)	C6—C7—H7	119.0
C2—N1—C1	117.24 (14)	C8—C7—C6	122.00 (14)
C3—N1—C1	121.77 (14)	C8—C7—H7	119.0
C3—N1—C2	120.95 (14)	C3—C8—H8	119.8
C9—N2—C10	117.63 (12)	C7—C8—C3	120.48 (14)
S1—N3—H31	114.2 (14)	C7—C8—H8	119.8
S1—N3—H32	111.8 (14)	N2—C9—C6	124.09 (13)
H32—N3—H31	116 (2)	N2—C9—H9	120.7 (11)
N1—C1—H1A	109.5	C6—C9—H9	115.2 (11)
N1—C1—H1B	109.5	C11—C10—N2	120.62 (13)
N1—C1—H1C	109.5	C15—C10—N2	119.72 (12)
H1A—C1—H1B	109.5	C15—C10—C11	119.52 (12)
H1A—C1—H1C	109.5	C10—C11—H11	119.8
H1B—C1—H1C	109.5	C12—C11—C10	120.31 (13)
N1—C2—H2A	109.5	C12—C11—H11	119.8
N1—C2—H2B	109.5	C11—C12—H12	120.2
N1—C2—H2C	109.5	C13—C12—C11	119.69 (13)
H2A—C2—H2B	109.5	C13—C12—H12	120.2
H2A—C2—H2C	109.5	C12—C13—S1	118.35 (11)
H2B—C2—H2C	109.5	C12—C13—C14	120.80 (12)
N1—C3—C4	120.90 (14)	C14—C13—S1	120.84 (11)
N1—C3—C8	121.80 (14)	C13—C14—C15	119.40 (13)
C8—C3—C4	117.27 (12)	C13—C14—H14	120.3
C3—C4—H4	119.4	C15—C14—H14	120.3
C5—C4—C3	121.27 (13)	C10—C15—H15	119.9
C5—C4—H4	119.4	C14—C15—C10	120.22 (13)
C4—C5—C6	121.37 (14)	C14—C15—H15	119.9
O1—S1—C13—C12	37.32 (14)	C7—C6—C5—C4	−0.9 (2)
O1—S1—C13—C14	−144.13 (13)	C9—C6—C5—C4	179.91 (14)
O2—S1—C13—C12	165.83 (13)	C5—C6—C7—C8	2.1 (2)
O2—S1—C13—C14	−15.62 (14)	C9—C6—C7—C8	−178.63 (14)
N3—S1—C13—C12	−77.72 (14)	C5—C6—C9—N2	−15.4 (2)
N3—S1—C13—C14	100.83 (13)	C7—C6—C9—N2	165.43 (16)
C10—N2—C9—C6	174.08 (13)	C6—C7—C8—C3	−1.9 (2)
C9—N2—C10—C11	−53.6 (2)	N2—C10—C11—C12	−178.14 (14)
C9—N2—C10—C15	130.68 (15)	C15—C10—C11—C12	−2.5 (2)
C4—C3—N1—C1	176.79 (15)	N2—C10—C15—C14	178.40 (13)
C4—C3—N1—C2	−1.0 (2)	C11—C10—C15—C14	2.7 (2)
C8—C3—N1—C1	−5.5 (2)	C13—C12—C11—C10	0.3 (2)
C8—C3—N1—C2	176.71 (16)	S1—C13—C12—C11	−179.80 (12)
N1—C3—C4—C5	178.58 (15)	C14—C13—C12—C11	1.7 (2)
C8—C3—C4—C5	0.8 (2)	S1—C13—C14—C15	−179.94 (11)
N1—C3—C8—C7	−177.33 (15)	C12—C13—C14—C15	−1.4 (2)
C4—C3—C8—C7	0.4 (2)	C13—C14—C15—C10	−0.8 (2)
C3—C4—C5—C6	−0.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N3—H31···N2i	0.80 (3)	2.18 (3)	2.981 (2)	177 (2)
N3—H32···O2ii	0.832 (19)	2.494 (19)	3.321 (2)	174 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H31⋯N2i	0.80 (3)	2.18 (3)	2.981 (2)	177 (2)
N3—H32⋯O2ii	0.832 (19)	2.494 (19)	3.321 (2)	174 (2)

Symmetry codes: (i) ; (ii) .