(E)-N'-(4-Bromo-benzyl-idene)-p-toluene-sulfonohydrazide.

In the title compound, C(14)H(13)BrN(2)O(2)S, a novel sulfonamide derivative, inter-molecular N-H⋯O and C-H⋯O hydrogen bonds link neighbouring mol-ecules into different dimers along the b axis, generating R(2) (2)(8) and R(2) (2)(16) ring motifs. The dihedral angle between the benzene rings is 82.39 (13)°. The crystal structure is further stabilized by inter-molecular π-π stacking inter-actions [centroid-centroid distances = 3.867 (2)-3.9548 (8) Å].

Related literature

For bond-length data, see: Allen et al. (1987 ▶). For hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures and applications, see, for example: Kia et al. (2008a ▶,b ▶); Tabatabaee et al. (2007 ▶); Ali et al. (2007 ▶); Tierney et al. 2006 ▶; Krygowski et al. (1998 ▶); Mehrabi et al. (2008 ▶); Kayser et al. (2004 ▶). For the stability of the temperature controller used for the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C14H13BrN2O2S

M = 353.23

Triclinic,

a = 5.9565 (3) Å

b = 9.4005 (3) Å

c = 12.8020 (6) Å

α = 97.153 (2)°

β = 96.350 (2)°

γ = 92.125 (1)°

V = 705.95 (5) Å3

Z = 2

Mo Kα radiation

μ = 3.06 mm−1

T = 100 K

0.57 × 0.15 × 0.07 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.276, T max = 0.819

18030 measured reflections

5040 independent reflections

4098 reflections with I > 2˘I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.106

S = 1.11

5040 reflections

187 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.63 e Å−3

Δρmin = −0.56 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809009751/rz2299sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809009751/rz2299Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H13BrN2O2S	Z = 2
Mr = 353.23	F(000) = 356
Triclinic, P1	Dx = 1.662 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.9565 (3) Å	Cell parameters from 7222 reflections
b = 9.4005 (3) Å	θ = 2.5–34.1°
c = 12.8020 (6) Å	µ = 3.06 mm−1
α = 97.153 (2)°	T = 100 K
β = 96.350 (2)°	Block, colourless
γ = 92.125 (1)°	0.57 × 0.14 × 0.07 mm
V = 705.95 (5) Å3

Bruker SMART APEXII CCD area-detector diffractometer	5040 independent reflections
Radiation source: fine-focus sealed tube	4098 reflections with I > 2˘I)
graphite	Rint = 0.034
φ and ω scans	θmax = 32.5°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −9→8
Tmin = 0.276, Tmax = 0.819	k = −14→14
18030 measured reflections	l = −18→19

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) = 0.106	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ2(Fo2) + (0.0387P)2 + 1.0631P] where P = (Fo2 + 2Fc2)/3
5040 reflections	(Δ/σ)max < 0.001
187 parameters	Δρmax = 0.63 e Å−3
0 restraints	Δρmin = −0.56 e Å−3

Experimental. The crystal was placed in the cold stream of an Oxford Cyrosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.

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
Br1	0.81285 (5)	0.24366 (3)	−0.11229 (2)	0.02400 (8)
S1	0.25512 (10)	0.69735 (6)	0.50609 (4)	0.01269 (11)
O1	0.1164 (3)	0.66003 (19)	0.58555 (14)	0.0166 (3)
O2	0.4777 (3)	0.76093 (19)	0.53840 (15)	0.0171 (3)
N1	0.2703 (4)	0.5426 (2)	0.43423 (17)	0.0147 (4)
N2	0.3865 (4)	0.5374 (2)	0.34562 (16)	0.0149 (4)
C1	−0.1178 (4)	0.7666 (3)	0.3846 (2)	0.0162 (4)
H1A	−0.1895	0.6830	0.4034	0.019*
C2	−0.2334 (4)	0.8507 (3)	0.3168 (2)	0.0187 (5)
H2A	−0.3851	0.8231	0.2884	0.022*
C3	−0.1313 (5)	0.9747 (3)	0.2894 (2)	0.0179 (5)
C4	0.0912 (5)	1.0145 (3)	0.3328 (2)	0.0194 (5)
H4A	0.1614	1.1000	0.3162	0.023*
C5	0.2112 (4)	0.9315 (3)	0.3994 (2)	0.0162 (4)
H5A	0.3632	0.9587	0.4275	0.019*
C6	0.1059 (4)	0.8075 (2)	0.42462 (19)	0.0139 (4)
C7	0.3238 (4)	0.4296 (3)	0.2753 (2)	0.0159 (4)
H7A	0.1980	0.3695	0.2850	0.019*
C8	0.4385 (4)	0.3958 (3)	0.18089 (19)	0.0156 (4)
C9	0.3420 (5)	0.2868 (3)	0.1030 (2)	0.0190 (5)
H9A	0.2005	0.2417	0.1106	0.023*
C10	0.4502 (5)	0.2435 (3)	0.0144 (2)	0.0208 (5)
H10A	0.3833	0.1699	−0.0387	0.025*
C11	0.6578 (4)	0.3098 (3)	0.0051 (2)	0.0176 (5)
C12	0.7559 (5)	0.4195 (3)	0.0805 (2)	0.0196 (5)
H12A	0.8971	0.4646	0.0722	0.023*
C13	0.6460 (5)	0.4627 (3)	0.1682 (2)	0.0180 (5)
H13A	0.7119	0.5381	0.2200	0.022*
C14	−0.2579 (5)	1.0639 (3)	0.2146 (2)	0.0255 (6)
H14A	−0.2504	1.1643	0.2471	0.038*
H14B	−0.4164	1.0282	0.2000	0.038*
H14C	−0.1893	1.0572	0.1481	0.038*
H1N1	0.160 (6)	0.483 (4)	0.436 (3)	0.020 (8)*

	U11	U22	U33	U12	U13	U23
Br1	0.02205 (14)	0.03319 (15)	0.01596 (12)	0.00426 (11)	0.00449 (10)	−0.00286 (10)
S1	0.0128 (3)	0.0121 (2)	0.0130 (2)	−0.00060 (19)	0.0009 (2)	0.00153 (18)
O1	0.0189 (9)	0.0168 (8)	0.0144 (8)	−0.0017 (7)	0.0046 (7)	0.0014 (6)
O2	0.0138 (8)	0.0154 (8)	0.0213 (9)	−0.0018 (6)	−0.0020 (7)	0.0039 (6)
N1	0.0160 (10)	0.0117 (8)	0.0167 (9)	−0.0009 (7)	0.0047 (8)	0.0009 (7)
N2	0.0151 (10)	0.0159 (9)	0.0141 (9)	0.0022 (7)	0.0030 (7)	0.0020 (7)
C1	0.0137 (11)	0.0157 (10)	0.0186 (11)	−0.0015 (8)	0.0005 (9)	0.0017 (8)
C2	0.0155 (11)	0.0206 (11)	0.0190 (11)	0.0027 (9)	−0.0012 (9)	0.0010 (9)
C3	0.0232 (13)	0.0135 (10)	0.0158 (10)	0.0046 (9)	−0.0007 (9)	−0.0011 (8)
C4	0.0237 (13)	0.0123 (10)	0.0219 (12)	0.0007 (9)	0.0014 (10)	0.0027 (9)
C5	0.0166 (11)	0.0138 (10)	0.0174 (11)	−0.0009 (8)	0.0007 (9)	0.0006 (8)
C6	0.0150 (10)	0.0131 (9)	0.0136 (10)	0.0004 (8)	0.0020 (8)	0.0017 (8)
C7	0.0154 (11)	0.0151 (10)	0.0178 (11)	0.0011 (8)	0.0029 (9)	0.0031 (8)
C8	0.0159 (11)	0.0159 (10)	0.0154 (10)	0.0034 (8)	0.0011 (9)	0.0036 (8)
C9	0.0168 (12)	0.0195 (11)	0.0202 (12)	0.0015 (9)	0.0013 (9)	0.0007 (9)
C10	0.0207 (13)	0.0228 (12)	0.0169 (11)	0.0010 (10)	0.0005 (10)	−0.0033 (9)
C11	0.0175 (11)	0.0214 (11)	0.0142 (10)	0.0045 (9)	0.0022 (9)	0.0023 (9)
C12	0.0188 (12)	0.0212 (11)	0.0197 (12)	0.0010 (9)	0.0055 (10)	0.0037 (9)
C13	0.0195 (12)	0.0170 (11)	0.0172 (11)	−0.0014 (9)	0.0028 (9)	0.0008 (9)
C14	0.0335 (16)	0.0178 (11)	0.0226 (13)	0.0073 (11)	−0.0081 (11)	0.0010 (9)

Br1—C11	1.901 (2)	C5—C6	1.393 (3)
S1—O2	1.4297 (19)	C5—H5A	0.9500
S1—O1	1.4469 (18)	C7—C8	1.460 (3)
S1—N1	1.633 (2)	C7—H7A	0.9500
S1—C6	1.756 (2)	C8—C9	1.396 (4)
N1—N2	1.389 (3)	C8—C13	1.400 (4)
N1—H1N1	0.85 (3)	C9—C10	1.390 (4)
N2—C7	1.283 (3)	C9—H9A	0.9500
C1—C2	1.390 (3)	C10—C11	1.388 (4)
C1—C6	1.395 (3)	C10—H10A	0.9500
C1—H1A	0.9500	C11—C12	1.385 (4)
C2—C3	1.396 (4)	C12—C13	1.387 (4)
C2—H2A	0.9500	C12—H12A	0.9500
C3—C4	1.398 (4)	C13—H13A	0.9500
C3—C14	1.509 (4)	C14—H14A	0.9800
C4—C5	1.386 (4)	C14—H14B	0.9800
C4—H4A	0.9500	C14—H14C	0.9800
O2—S1—O1	119.47 (11)	N2—C7—C8	122.5 (2)
O2—S1—N1	109.68 (11)	N2—C7—H7A	118.8
O1—S1—N1	102.07 (11)	C8—C7—H7A	118.8
O2—S1—C6	108.68 (11)	C9—C8—C13	119.0 (2)
O1—S1—C6	109.36 (11)	C9—C8—C7	118.2 (2)
N1—S1—C6	106.81 (11)	C13—C8—C7	122.7 (2)
N2—N1—S1	118.59 (16)	C10—C9—C8	120.9 (2)
N2—N1—H1N1	120 (2)	C10—C9—H9A	119.5
S1—N1—H1N1	114 (2)	C8—C9—H9A	119.5
C7—N2—N1	113.5 (2)	C11—C10—C9	118.7 (2)
C2—C1—C6	118.6 (2)	C11—C10—H10A	120.6
C2—C1—H1A	120.7	C9—C10—H10A	120.6
C6—C1—H1A	120.7	C12—C11—C10	121.6 (2)
C1—C2—C3	121.4 (2)	C12—C11—Br1	119.75 (19)
C1—C2—H2A	119.3	C10—C11—Br1	118.67 (19)
C3—C2—H2A	119.3	C11—C12—C13	119.3 (2)
C2—C3—C4	118.5 (2)	C11—C12—H12A	120.4
C2—C3—C14	120.8 (2)	C13—C12—H12A	120.4
C4—C3—C14	120.6 (2)	C12—C13—C8	120.5 (2)
C5—C4—C3	121.2 (2)	C12—C13—H13A	119.8
C5—C4—H4A	119.4	C8—C13—H13A	119.8
C3—C4—H4A	119.4	C3—C14—H14A	109.5
C4—C5—C6	119.1 (2)	C3—C14—H14B	109.5
C4—C5—H5A	120.5	H14A—C14—H14B	109.5
C6—C5—H5A	120.5	C3—C14—H14C	109.5
C5—C6—C1	121.2 (2)	H14A—C14—H14C	109.5
C5—C6—S1	120.30 (19)	H14B—C14—H14C	109.5
C1—C6—S1	118.52 (18)
O2—S1—N1—N2	−54.7 (2)	O2—S1—C6—C1	−179.30 (19)
O1—S1—N1—N2	177.61 (18)	O1—S1—C6—C1	−47.3 (2)
C6—S1—N1—N2	62.9 (2)	N1—S1—C6—C1	62.4 (2)
S1—N1—N2—C7	−156.20 (19)	N1—N2—C7—C8	−173.9 (2)
C6—C1—C2—C3	−0.8 (4)	N2—C7—C8—C9	−172.5 (2)
C1—C2—C3—C4	−0.6 (4)	N2—C7—C8—C13	10.9 (4)
C1—C2—C3—C14	179.2 (2)	C13—C8—C9—C10	0.7 (4)
C2—C3—C4—C5	1.6 (4)	C7—C8—C9—C10	−176.0 (2)
C14—C3—C4—C5	−178.3 (2)	C8—C9—C10—C11	0.6 (4)
C3—C4—C5—C6	−1.0 (4)	C9—C10—C11—C12	−1.5 (4)
C4—C5—C6—C1	−0.5 (4)	C9—C10—C11—Br1	176.8 (2)
C4—C5—C6—S1	178.40 (19)	C10—C11—C12—C13	1.0 (4)
C2—C1—C6—C5	1.4 (4)	Br1—C11—C12—C13	−177.21 (19)
C2—C1—C6—S1	−177.52 (19)	C11—C12—C13—C8	0.3 (4)
O2—S1—C6—C5	1.8 (2)	C9—C8—C13—C12	−1.2 (4)
O1—S1—C6—C5	133.8 (2)	C7—C8—C13—C12	175.4 (2)
N1—S1—C6—C5	−116.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···O1i	0.85 (4)	2.06 (4)	2.902 (3)	171 (4)
C14—H14A···O1ii	0.98	2.57	3.420 (3)	145

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯O1i	0.85 (4)	2.06 (4)	2.902 (3)	171 (4)
C14—H14A⋯O1ii	0.98	2.57	3.420 (3)	145

Symmetry codes: (i) ; (ii) .