(E)-N'-(5-Bromo-2-hydroxy-benzyl-idene)-p-toluene-sulfonohydrazide.

The title compound, C(14)H(13)BrN(2)O(3)S, features an intra-molecular O-H⋯N hydrogen bond which generates an S(6) ring motif. The dihedral angle between the two benzene rings is 86.47 (6)°. Inter-molecular N-H⋯O and C-H⋯O inter-actions link neighbouring mol-ecules via R(2) (2)(13) ring motifs, forming one-dimensional extended chains along the c axis.

Related literature

For background to sulfonamides, see: Kayser et al. (2004 ▶). For details of hydrogen-bond motifs, see: Bernstein et al. (1995 ▶). For related structures and applications see: Tabatabaee et al. (2007 ▶); Mehrabi et al. (2008 ▶); Ali et al. (2007 ▶); Tierney et al. (2006 ▶); Krygowski et al. (1998 ▶).

Experimental

Crystal data

C14H13BrN2O3S

M = 369.23

Monoclinic,

a = 15.8890 (3) Å

b = 9.8502 (2) Å

c = 9.8702 (2) Å

β = 105.475 (1)°

V = 1488.78 (5) Å3

Z = 4

Mo Kα radiation

μ = 2.91 mm−1

T = 100.0 (1) K

0.45 × 0.34 × 0.31 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (; Bruker, 2005 ▶) T min = 0.308, T max = 0.407

41486 measured reflections

7057 independent reflections

5961 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.079

S = 1.06

7057 reflections

199 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.28 e Å−3

Δρmin = −0.59 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: APEX2; data reduction: SAINT (Bruker, 2005 ▶); 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, 2003 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808037069/tk2325sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808037069/tk2325Isup2.hkl

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

C14H13BrN2O3S	F000 = 744
Mr = 369.23	Dx = 1.647 Mg m−3
Monoclinic, P21/c	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9995 reflections
a = 15.8890 (3) Å	θ = 2.5–37.4º
b = 9.8502 (2) Å	µ = 2.91 mm−1
c = 9.8702 (2) Å	T = 100 (1) K
β = 105.475 (1)º	Block, colourless
V = 1488.78 (5) Å3	0.45 × 0.34 × 0.31 mm
Z = 4

Bruker SMART APEXII CCD area-detector diffractometer	7057 independent reflections
Radiation source: fine-focus sealed tube	5961 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.035
T = 100(1) K	θmax = 36.0º
φ and ω scans	θmin = 1.3º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −26→25
Tmin = 0.308, Tmax = 0.407	k = −16→16
41486 measured reflections	l = −16→16

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)] = 0.028	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.079	w = 1/[σ2(Fo2) + (0.0378P)2 + 0.5647P] where P = (Fo2 + 2Fc2)/3
S = 1.06	(Δ/σ)max = 0.003
7057 reflections	Δρmax = 1.28 e Å−3
199 parameters	Δρmin = −0.59 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

Experimental. The low-temperature data was collected with the Oxford Cyrosystem Cobra low-temperature attachment.

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	1.191754 (8)	0.636650 (14)	1.149579 (15)	0.02941 (4)
S1	0.645085 (17)	0.74186 (3)	0.60027 (3)	0.01571 (5)
O1	0.91105 (6)	0.56509 (11)	0.60615 (10)	0.02610 (17)
O2	0.67053 (6)	0.78504 (9)	0.47792 (9)	0.02295 (16)
O3	0.57441 (5)	0.80755 (8)	0.63807 (9)	0.02088 (15)
N1	0.80775 (6)	0.71072 (9)	0.72484 (10)	0.01769 (15)
N2	0.73002 (6)	0.77064 (9)	0.73584 (10)	0.01728 (15)
C1	0.97310 (8)	0.58383 (12)	0.72937 (13)	0.02124 (19)
C2	1.05653 (9)	0.53277 (14)	0.74093 (15)	0.0272 (2)
H2A	1.0683	0.4878	0.6652	0.033*
C3	1.12225 (8)	0.54873 (14)	0.86523 (15)	0.0279 (2)
H3A	1.1778	0.5144	0.8729	0.033*
C4	1.10429 (8)	0.61625 (12)	0.97777 (14)	0.0237 (2)
C5	1.02200 (8)	0.66843 (12)	0.96797 (13)	0.02211 (19)
H5A	1.0110	0.7138	1.0441	0.027*
C6	0.95532 (7)	0.65296 (11)	0.84359 (12)	0.01914 (18)
C7	0.86985 (7)	0.70900 (11)	0.83885 (12)	0.01990 (18)
H7A	0.8600	0.7445	0.9206	0.024*
C8	0.62834 (7)	0.56588 (10)	0.59177 (11)	0.01615 (16)
C9	0.66712 (8)	0.48649 (11)	0.50865 (12)	0.02087 (19)
H9A	0.6983	0.5265	0.4518	0.025*
C10	0.65842 (8)	0.34621 (11)	0.51211 (13)	0.0223 (2)
H10A	0.6841	0.2924	0.4567	0.027*
C11	0.61190 (7)	0.28427 (11)	0.59702 (12)	0.01949 (18)
C12	0.57195 (8)	0.36678 (11)	0.67689 (13)	0.02032 (18)
H12A	0.5393	0.3271	0.7318	0.024*
C13	0.58016 (7)	0.50714 (11)	0.67562 (12)	0.01874 (17)
H13A	0.5539	0.5612	0.7300	0.022*
C14	0.60620 (9)	0.13240 (11)	0.60308 (15)	0.0257 (2)
H14A	0.6230	0.0935	0.5250	0.039*
H14B	0.5473	0.1063	0.5986	0.039*
H14C	0.6446	0.1003	0.6894	0.039*
H1N2	0.7171 (12)	0.7519 (19)	0.812 (2)	0.027 (4)*
H1O1	0.8634 (18)	0.596 (3)	0.615 (3)	0.057 (7)*

	U11	U22	U33	U12	U13	U23
Br1	0.01916 (6)	0.02972 (7)	0.03454 (8)	−0.00490 (4)	−0.00119 (5)	0.00973 (5)
S1	0.01756 (10)	0.01561 (10)	0.01476 (10)	0.00098 (7)	0.00568 (8)	0.00033 (7)
O1	0.0248 (4)	0.0345 (5)	0.0198 (4)	0.0064 (3)	0.0074 (3)	0.0009 (3)
O2	0.0322 (4)	0.0216 (3)	0.0178 (4)	0.0002 (3)	0.0114 (3)	0.0031 (3)
O3	0.0191 (3)	0.0196 (3)	0.0246 (4)	0.0042 (3)	0.0069 (3)	−0.0005 (3)
N1	0.0164 (4)	0.0173 (3)	0.0206 (4)	0.0000 (3)	0.0071 (3)	0.0001 (3)
N2	0.0165 (4)	0.0191 (4)	0.0171 (4)	−0.0003 (3)	0.0059 (3)	−0.0025 (3)
C1	0.0217 (5)	0.0216 (4)	0.0217 (5)	0.0026 (4)	0.0081 (4)	0.0037 (4)
C2	0.0245 (5)	0.0295 (5)	0.0305 (6)	0.0072 (4)	0.0122 (5)	0.0035 (5)
C3	0.0208 (5)	0.0282 (5)	0.0359 (7)	0.0051 (4)	0.0095 (5)	0.0075 (5)
C4	0.0172 (4)	0.0233 (5)	0.0290 (6)	−0.0010 (4)	0.0035 (4)	0.0069 (4)
C5	0.0189 (5)	0.0213 (4)	0.0251 (5)	−0.0017 (4)	0.0042 (4)	0.0007 (4)
C6	0.0178 (4)	0.0181 (4)	0.0218 (5)	0.0002 (3)	0.0057 (4)	0.0017 (3)
C7	0.0181 (4)	0.0199 (4)	0.0219 (5)	−0.0005 (3)	0.0057 (4)	−0.0023 (4)
C8	0.0168 (4)	0.0161 (4)	0.0154 (4)	−0.0003 (3)	0.0040 (3)	−0.0008 (3)
C9	0.0253 (5)	0.0193 (4)	0.0211 (5)	−0.0006 (4)	0.0114 (4)	−0.0023 (4)
C10	0.0263 (5)	0.0184 (4)	0.0238 (5)	0.0005 (4)	0.0094 (4)	−0.0037 (4)
C11	0.0181 (4)	0.0174 (4)	0.0209 (5)	−0.0002 (3)	0.0015 (4)	0.0004 (3)
C12	0.0187 (4)	0.0201 (4)	0.0228 (5)	−0.0018 (3)	0.0067 (4)	0.0016 (4)
C13	0.0175 (4)	0.0197 (4)	0.0205 (4)	−0.0001 (3)	0.0075 (3)	−0.0002 (3)
C14	0.0291 (6)	0.0171 (4)	0.0286 (6)	−0.0001 (4)	0.0035 (5)	0.0009 (4)

Br1—C4	1.8947 (13)	C5—H5A	0.9300
S1—O3	1.4292 (8)	C6—C7	1.4551 (16)
S1—O2	1.4363 (9)	C7—H7A	0.9300
S1—N2	1.6518 (10)	C8—C9	1.3907 (15)
S1—C8	1.7524 (10)	C8—C13	1.3943 (15)
O1—C1	1.3585 (16)	C9—C10	1.3900 (16)
O1—H1O1	0.84 (3)	C9—H9A	0.9300
N1—C7	1.2837 (15)	C10—C11	1.3971 (17)
N1—N2	1.3989 (13)	C10—H10A	0.9300
N2—H1N2	0.852 (19)	C11—C12	1.3972 (16)
C1—C2	1.3937 (17)	C11—C14	1.5008 (16)
C1—C6	1.4087 (16)	C12—C13	1.3891 (15)
C2—C3	1.392 (2)	C12—H12A	0.9300
C2—H2A	0.9300	C13—H13A	0.9300
C3—C4	1.388 (2)	C14—H14A	0.9600
C3—H3A	0.9300	C14—H14B	0.9600
C4—C5	1.3840 (17)	C14—H14C	0.9600
C5—C6	1.3995 (17)
O3—S1—O2	120.16 (5)	C1—C6—C7	122.85 (11)
O3—S1—N2	103.88 (5)	N1—C7—C6	121.72 (10)
O2—S1—N2	106.13 (5)	N1—C7—H7A	119.1
O3—S1—C8	109.91 (5)	C6—C7—H7A	119.1
O2—S1—C8	109.02 (5)	C9—C8—C13	121.11 (10)
N2—S1—C8	106.82 (5)	C9—C8—S1	119.93 (8)
C1—O1—H1O1	108.2 (18)	C13—C8—S1	118.85 (8)
C7—N1—N2	115.19 (9)	C10—C9—C8	118.81 (10)
N1—N2—S1	114.34 (7)	C10—C9—H9A	120.6
N1—N2—H1N2	113.8 (13)	C8—C9—H9A	120.6
S1—N2—H1N2	110.0 (13)	C9—C10—C11	121.39 (10)
O1—C1—C2	118.13 (11)	C9—C10—H10A	119.3
O1—C1—C6	121.98 (10)	C11—C10—H10A	119.3
C2—C1—C6	119.89 (12)	C10—C11—C12	118.51 (10)
C3—C2—C1	120.33 (12)	C10—C11—C14	120.42 (11)
C3—C2—H2A	119.8	C12—C11—C14	121.07 (11)
C1—C2—H2A	119.8	C13—C12—C11	121.06 (10)
C4—C3—C2	119.57 (11)	C13—C12—H12A	119.5
C4—C3—H3A	120.2	C11—C12—H12A	119.5
C2—C3—H3A	120.2	C12—C13—C8	119.09 (10)
C5—C4—C3	120.94 (12)	C12—C13—H13A	120.5
C5—C4—Br1	118.48 (10)	C8—C13—H13A	120.5
C3—C4—Br1	120.58 (9)	C11—C14—H14A	109.5
C4—C5—C6	120.05 (12)	C11—C14—H14B	109.5
C4—C5—H5A	120.0	H14A—C14—H14B	109.5
C6—C5—H5A	120.0	C11—C14—H14C	109.5
C5—C6—C1	119.22 (11)	H14A—C14—H14C	109.5
C5—C6—C7	117.93 (10)	H14B—C14—H14C	109.5
C7—N1—N2—S1	−166.98 (8)	C5—C6—C7—N1	173.17 (11)
O3—S1—N2—N1	177.80 (7)	C1—C6—C7—N1	−7.24 (17)
O2—S1—N2—N1	−54.59 (9)	O3—S1—C8—C9	155.48 (9)
C8—S1—N2—N1	61.63 (8)	O2—S1—C8—C9	21.84 (11)
O1—C1—C2—C3	−179.66 (12)	N2—S1—C8—C9	−92.44 (10)
C6—C1—C2—C3	0.54 (19)	O3—S1—C8—C13	−28.24 (10)
C1—C2—C3—C4	−0.2 (2)	O2—S1—C8—C13	−161.87 (9)
C2—C3—C4—C5	−0.25 (19)	N2—S1—C8—C13	83.85 (9)
C2—C3—C4—Br1	178.81 (10)	C13—C8—C9—C10	−1.12 (18)
C3—C4—C5—C6	0.31 (18)	S1—C8—C9—C10	175.08 (9)
Br1—C4—C5—C6	−178.78 (9)	C8—C9—C10—C11	−0.07 (19)
C4—C5—C6—C1	0.06 (17)	C9—C10—C11—C12	1.54 (18)
C4—C5—C6—C7	179.67 (11)	C9—C10—C11—C14	−177.72 (12)
O1—C1—C6—C5	179.73 (11)	C10—C11—C12—C13	−1.87 (18)
C2—C1—C6—C5	−0.48 (17)	C14—C11—C12—C13	177.39 (11)
O1—C1—C6—C7	0.14 (17)	C11—C12—C13—C8	0.73 (18)
C2—C1—C6—C7	179.92 (11)	C9—C8—C13—C12	0.80 (17)
N2—N1—C7—C6	−178.58 (10)	S1—C8—C13—C12	−175.44 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H1N2···O2i	0.851 (19)	2.002 (19)	2.8476 (13)	172.4 (19)
O1—H1O1···N1	0.84 (3)	1.94 (3)	2.6740 (14)	146 (3)
C7—H7A···O1i	0.93	2.60	3.3793 (15)	142
C10—H10A···Br1ii	0.93	2.91	3.8082 (12)	164
C12—H12A···O3iii	0.93	2.49	3.3691 (15)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H1N2⋯O2i	0.851 (19)	2.002 (19)	2.8476 (13)	172.4 (19)
O1—H1O1⋯N1	0.84 (3)	1.94 (3)	2.6740 (14)	146 (3)
C7—H7A⋯O1i	0.93	2.60	3.3793 (15)	142
C10—H10A⋯Br1ii	0.93	2.91	3.8082 (12)	164
C12—H12A⋯O3iii	0.93	2.49	3.3691 (15)	158

Symmetry codes: (i) ; (ii) ; (iii) .