4-[(E)-(5-Bromo-2-hydroxy-phen-yl)methyl-ideneamino]benzene-sulfonamide.

In the title compound, C(13)H(11)ClN(2)O(3)S, the dihedral angle between the benzene rings is 12.26 (33)° and an intra-molecular O-H⋯N hydrogen bond helps to establish the conformation. In the crystal, N-H⋯O and C-H⋯O inter-actions link the mol-ecules.

Related literature

For a related structure and background discussion, see: Chohan et al. (2009 ▶). For graph-set theory, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C13H11BrN2O3S

M = 355.21

Monoclinic,

a = 6.1224 (15) Å

b = 4.5263 (13) Å

c = 23.445 (9) Å

β = 94.44 (2)°

V = 647.8 (3) Å3

Z = 2

Mo Kα radiation

μ = 3.34 mm−1

T = 100 K

0.22 × 0.20 × 0.16 mm

Data collection

Bruker Kappa APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.482, T max = 0.587

3181 measured reflections

1653 independent reflections

1458 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.087

S = 1.00

1653 reflections

188 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.71 e Å−3

Δρmin = −1.13 e Å−3

Absolute structure: Flack (1983 ▶), 279 Friedal pairs

Flack parameter: 0.025 (16)

Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); 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, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶) and PLATON.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809036010/hb5090sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809036010/hb5090Isup2.hkl

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

C13H11BrN2O3S	F(000) = 356
Mr = 355.21	Dx = 1.821 Mg m−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 1653 reflections
a = 6.1224 (15) Å	θ = 3.3–25.5°
b = 4.5263 (13) Å	µ = 3.34 mm−1
c = 23.445 (9) Å	T = 100 K
β = 94.44 (2)°	Prismatic, yellow
V = 647.8 (3) Å3	0.22 × 0.20 × 0.16 mm
Z = 2

Bruker Kappa APEXII CCD diffractometer	1653 independent reflections
Radiation source: fine-focus sealed tube	1458 reflections with I > 2σ(I)
graphite	Rint = 0.042
Detector resolution: 7.80 pixels mm-1	θmax = 25.5°, θmin = 3.3°
ω scans	h = −6→7
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −2→5
Tmin = 0.482, Tmax = 0.587	l = −28→28
3181 measured reflections

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)] = 0.037	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.087	w = 1/[σ2(Fo2) + (0.0554P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max = 0.001
1653 reflections	Δρmax = 0.71 e Å−3
188 parameters	Δρmin = −1.13 e Å−3
1 restraint	Absolute structure: Flack (1983), 279 Friedal pairs
Primary atom site location: structure-invariant direct methods	Flack parameter: 0.025 (16)

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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	0.22142 (8)	1.43584 (16)	0.03133 (2)	0.0184 (2)
S1	0.2382 (2)	−0.1521 (3)	0.42877 (6)	0.0131 (4)
O1	0.8682 (5)	0.9320 (15)	0.21201 (14)	0.0184 (11)
O2	0.0460 (7)	−0.3040 (10)	0.40583 (17)	0.0175 (12)
O3	0.4146 (6)	−0.3217 (10)	0.45633 (17)	0.0148 (12)
N1	0.5538 (8)	0.6166 (11)	0.2472 (2)	0.0141 (16)
N2	0.1639 (9)	0.0737 (13)	0.4770 (2)	0.0166 (17)
C1	0.5019 (8)	0.947 (2)	0.16824 (19)	0.0124 (14)
C2	0.7192 (9)	1.0429 (15)	0.1723 (2)	0.0134 (16)
C3	0.7829 (9)	1.2590 (14)	0.1347 (2)	0.0148 (17)
C4	0.6381 (9)	1.3763 (12)	0.0932 (2)	0.0143 (19)
C5	0.4222 (9)	1.2702 (14)	0.0883 (2)	0.0120 (17)
C6	0.3552 (10)	1.0646 (14)	0.1257 (2)	0.0149 (17)
C7	0.4239 (9)	0.7346 (14)	0.2085 (2)	0.0134 (17)
C8	0.4747 (8)	0.4182 (18)	0.2878 (2)	0.0114 (14)
C9	0.6126 (9)	0.3535 (13)	0.3358 (2)	0.0147 (19)
C10	0.5457 (10)	0.1737 (14)	0.3780 (3)	0.0155 (17)
C11	0.3363 (9)	0.0532 (14)	0.3724 (2)	0.0135 (17)
C12	0.1995 (9)	0.1113 (13)	0.3242 (2)	0.0134 (17)
C13	0.2664 (9)	0.2936 (14)	0.2818 (2)	0.0145 (17)
H1	0.81278	0.79686	0.22919	0.0218*
H3	0.92711	1.32519	0.13772	0.0176*
H4	0.68212	1.52308	0.06879	0.0172*
H6	0.21007	1.00207	0.12277	0.0178*
H7	0.27623	0.68391	0.20607	0.0155*
H9	0.75293	0.43345	0.33940	0.0177*
H10	0.63936	0.13250	0.41016	0.0182*
H12	0.06076	0.02660	0.32024	0.0159*
H13	0.17312	0.33314	0.24953	0.0172*
H21	0.258 (12)	0.139 (18)	0.493 (3)	0.0197*
H22	0.062 (11)	0.200 (17)	0.460 (3)	0.0197*

	U11	U22	U33	U12	U13	U23
Br1	0.0216 (3)	0.0200 (3)	0.0131 (3)	0.0009 (4)	−0.0012 (2)	0.0024 (3)
S1	0.0143 (7)	0.0109 (8)	0.0142 (7)	−0.0014 (6)	0.0010 (5)	0.0006 (5)
O1	0.0173 (18)	0.019 (2)	0.0186 (18)	−0.009 (3)	0.0003 (14)	0.010 (3)
O2	0.017 (2)	0.017 (2)	0.018 (2)	−0.006 (2)	−0.0015 (17)	0.0027 (19)
O3	0.014 (2)	0.013 (2)	0.017 (2)	0.0027 (18)	−0.0014 (17)	0.0053 (17)
N1	0.013 (2)	0.013 (3)	0.017 (3)	−0.002 (2)	0.005 (2)	−0.001 (2)
N2	0.018 (3)	0.010 (3)	0.022 (3)	−0.001 (3)	0.003 (2)	−0.001 (2)
C1	0.015 (2)	0.010 (3)	0.013 (2)	0.005 (4)	0.0056 (19)	−0.006 (4)
C2	0.017 (3)	0.018 (3)	0.005 (2)	−0.001 (3)	0.000 (2)	−0.003 (2)
C3	0.011 (3)	0.011 (3)	0.023 (3)	−0.002 (3)	0.006 (2)	0.004 (3)
C4	0.020 (3)	0.008 (4)	0.016 (3)	−0.005 (3)	0.009 (2)	0.001 (2)
C5	0.016 (3)	0.010 (3)	0.010 (3)	0.005 (3)	0.002 (2)	−0.006 (2)
C6	0.015 (3)	0.015 (3)	0.015 (3)	−0.001 (3)	0.003 (2)	−0.004 (3)
C7	0.013 (3)	0.008 (3)	0.020 (3)	−0.004 (3)	0.007 (2)	−0.002 (3)
C8	0.017 (2)	0.004 (3)	0.014 (2)	0.002 (3)	0.006 (2)	0.001 (3)
C9	0.009 (3)	0.010 (4)	0.025 (3)	−0.002 (2)	0.001 (2)	−0.002 (2)
C10	0.017 (3)	0.016 (3)	0.013 (3)	0.001 (3)	−0.002 (2)	0.003 (3)
C11	0.017 (3)	0.008 (3)	0.016 (3)	0.001 (3)	0.005 (2)	0.001 (2)
C12	0.012 (3)	0.014 (3)	0.014 (3)	−0.004 (3)	0.000 (2)	−0.001 (3)
C13	0.016 (3)	0.013 (3)	0.014 (3)	0.002 (3)	−0.002 (2)	−0.002 (3)

Br1—C5	1.898 (5)	C4—C5	1.403 (8)
S1—O2	1.431 (5)	C5—C6	1.363 (8)
S1—O3	1.437 (4)	C8—C13	1.392 (8)
S1—N2	1.616 (5)	C8—C9	1.385 (7)
S1—C11	1.759 (6)	C9—C10	1.368 (9)
O1—C2	1.349 (7)	C10—C11	1.390 (8)
O1—H1	0.8200	C11—C12	1.379 (7)
N1—C8	1.421 (8)	C12—C13	1.378 (8)
N1—C7	1.276 (7)	C3—H3	0.9300
N2—H21	0.73 (8)	C4—H4	0.9300
N2—H22	0.92 (7)	C6—H6	0.9300
C1—C7	1.454 (9)	C7—H7	0.9300
C1—C6	1.395 (8)	C9—H9	0.9300
C1—C2	1.396 (8)	C10—H10	0.9300
C2—C3	1.393 (8)	C12—H12	0.9300
C3—C4	1.372 (7)	C13—H13	0.9300
O2—S1—O3	118.7 (3)	C9—C8—C13	119.5 (5)
O2—S1—N2	107.4 (3)	N1—C8—C9	117.4 (5)
O2—S1—C11	106.9 (3)	C8—C9—C10	121.0 (5)
O3—S1—N2	105.4 (3)	C9—C10—C11	119.4 (6)
O3—S1—C11	109.4 (3)	S1—C11—C10	120.2 (4)
N2—S1—C11	108.8 (3)	C10—C11—C12	120.0 (5)
C2—O1—H1	109.00	S1—C11—C12	119.7 (4)
C7—N1—C8	121.0 (5)	C11—C12—C13	120.6 (5)
S1—N2—H22	108 (5)	C8—C13—C12	119.4 (5)
S1—N2—H21	111 (6)	C2—C3—H3	119.00
H21—N2—H22	117 (8)	C4—C3—H3	119.00
C2—C1—C6	119.2 (6)	C3—C4—H4	121.00
C2—C1—C7	121.4 (5)	C5—C4—H4	121.00
C6—C1—C7	119.4 (5)	C1—C6—H6	120.00
O1—C2—C1	121.4 (5)	C5—C6—H6	120.00
C1—C2—C3	119.2 (5)	N1—C7—H7	119.00
O1—C2—C3	119.4 (5)	C1—C7—H7	119.00
C2—C3—C4	121.6 (5)	C8—C9—H9	119.00
C3—C4—C5	118.6 (5)	C10—C9—H9	119.00
C4—C5—C6	120.6 (5)	C9—C10—H10	120.00
Br1—C5—C4	118.5 (4)	C11—C10—H10	120.00
Br1—C5—C6	120.8 (4)	C11—C12—H12	120.00
C1—C6—C5	120.7 (6)	C13—C12—H12	120.00
N1—C7—C1	121.4 (5)	C8—C13—H13	120.00
N1—C8—C13	123.1 (5)	C12—C13—H13	120.00
O2—S1—C11—C10	−166.2 (5)	O1—C2—C3—C4	179.3 (5)
O2—S1—C11—C12	18.2 (6)	C1—C2—C3—C4	−1.1 (9)
O3—S1—C11—C10	−36.6 (6)	C2—C3—C4—C5	−1.2 (8)
O3—S1—C11—C12	147.9 (5)	C3—C4—C5—Br1	179.4 (4)
N2—S1—C11—C10	78.1 (6)	C3—C4—C5—C6	3.0 (8)
N2—S1—C11—C12	−97.5 (5)	Br1—C5—C6—C1	−178.8 (5)
C8—N1—C7—C1	177.5 (6)	C4—C5—C6—C1	−2.5 (9)
C7—N1—C8—C9	−165.3 (6)	N1—C8—C9—C10	177.4 (6)
C7—N1—C8—C13	13.4 (10)	C13—C8—C9—C10	−1.3 (10)
C6—C1—C2—O1	−178.8 (6)	N1—C8—C13—C12	−177.7 (6)
C6—C1—C2—C3	1.6 (10)	C9—C8—C13—C12	1.0 (9)
C7—C1—C2—O1	3.2 (10)	C8—C9—C10—C11	0.3 (9)
C7—C1—C2—C3	−176.4 (6)	C9—C10—C11—S1	−174.5 (5)
C2—C1—C6—C5	0.2 (10)	C9—C10—C11—C12	1.1 (9)
C7—C1—C6—C5	178.2 (6)	S1—C11—C12—C13	174.2 (5)
C2—C1—C7—N1	−3.7 (10)	C10—C11—C12—C13	−1.4 (9)
C6—C1—C7—N1	178.3 (6)	C11—C12—C13—C8	0.4 (9)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1	0.82	1.86	2.583 (7)	146
N2—H21···O3i	0.73 (8)	2.26 (7)	2.950 (7)	160 (8)
N2—H22···O2ii	0.92 (7)	2.58 (8)	3.325 (7)	139 (6)
C9—H9···O2iii	0.93	2.57	3.386 (7)	146

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1	0.82	1.86	2.583 (7)	146
N2—H21⋯O3i	0.73 (8)	2.26 (7)	2.950 (7)	160 (8)
N2—H22⋯O2ii	0.92 (7)	2.58 (8)	3.325 (7)	139 (6)
C9—H9⋯O2iii	0.93	2.57	3.386 (7)	146

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