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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoIUCrDATA
ISSN: 2414-3146
Volume 1| Part 4| April 2016| x160631
doi:10.1107/S2414314616006313

4-Bromo-N-(4-bromo­phen­yl)benzene­sulfonamide

Vinola Z. Rodrigues,a S. Naveen,b N. K. Lokanathc and P. A. Suchetand*

aDepartment of PG Studies and Research in Chemistry, St. Aloysius College, Mangalore, India, bInstitution of Excellence, University of Mysore, Manasagangotri, Mysuru-6, India, cDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysuru-6, India, and dDepartment of Chemistry, University College of Science, Tumkur University, Tumkur 572 103, India
*Correspondence e-mail: pasuchetan@yahoo.co.in

Edited by O. Blacque, University of Zürich, Switzerland (Received 12 April 2016; accepted 14 April 2016; online 19 April 2016)

The mol­ecule of the title compound, C12H9Br2NO2S, is U shaped with the central C—S—N—C segment having a torsion angle of 63.2 (4)°. Further, the dihedral angle between the benzene rings is 38.5 (2)°. The crystal structure features strong N—H⋯O hydrogen bonds that form infinite [100] C(4) chains. Mol­ecules in adjacent chains are inter­linked via C—H⋯O inter­actions which run along the b axis, forming C(7) chains. This results in a two-dimensional network in the ab plane; adjacent networks are connected by short Br⋯Br contacts [3.5092 (8) Å] propagating along the diagonal of the ac plane, so that a three-dimensional supra­molecular architecture ensues.

CCDC reference: 1474176

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Sulfonamide drugs were the first chemotherapeutic agents to be used to cure and prevent bacterial infection in human beings (Shiva Prasad et al., 2011[Shiva Prasad, K., Shiva Kumara, L., Vinay, K. B., Chandra Shekar, S., Jayalakshmi, B. & Revanasiddappa, H. D. (2011). Int. J. Chem. Res. 2, 1-6.]). They play a vital role as key constituents in a number of biologically active mol­ecules being known to exhibit a wide variety of biological activities such as anti­bacterial (Subhakara Reddy et al., 2012[Subhakara Reddy, N., Srinivas Rao, A., Adharvana Chari, M., Ravi Kumar, V., Jyothy, V. & Himabindu, V. (2012). J. Chem. Sci. 124, 723-730.]), insecticidal (Himel et al., 1971[Himel, C. M., Aboul-Saad, W. G. & Uk, S. (1971). J. Agric. Food Chem. 19, 1175-1180.]), anti­fungal (Hanafy et al., 2007[Hanafy, A., Uno, J., Mitani, H., Kang, Y. & Mikami, Y. (2007). Jpn J. Med. Mycol. 48, 47-50.]), anti­hepatitis (Yan-Fang et al., 2010[Yan-Fang, Z., Run-Liang, F., Ya-Jing, L., Yi-Kun, Z. & Ping, G. (2010). Chem. Res. Chin. Univ. 26, 272-277.]), anti-inflamatory (Küçükgüzel et al., 2013[Küçükgüzel, Ş., Coşkun, I., İnci, , Aydın, S., Aktay, G., Gürsoy, , Şule, , Çevik, Ö., Özakpınar, Ö., Özsavcı, D., Şener, A., Kaushik-Basu, N., Basu, A. & Talele, T. (2013). Molecules, 18, 3595-3614.]), anti­tumor (Ghorab et al., 2011[Ghorab, M. M., Ragab, A. F., Heiba, I. H. & Agha, M. H. (2011). J. Basic Appl. Chem. 1(2), 8-14.]), anti­cancer (Al-Said et al., 2011[Al-Said, M. S., Ghorab, M. M., Al-Dosari, M. S. & Hamed, M. M. (2011). Eur. J. Med. Chem. 46, 201-207.]), anti-HIV (Sahu et al., 2007[Sahu, K. K., Ravichandran, V., Mourya, V. K. & Agrawal, R. K. (2007). Med. Chem. Res. 15, 418-430.]) and anti­tubercular activities (Vora et al., 2012[Vora, P. J. & Mehta, A. G. (2012). IOSR J. Appl. Chem. 1(4), 34-39.]). In recent years, extensive research has been carried out on the synthesis and evaluation of the pharmacological activities of mol­ecules containing the sulfonamide moiety, and they have been reported to be important pharmacophores (Mohan et al., 2013[Mohan, N. R., Sreenivasa, S., Manojkumar, K. E. & Chakrapani Rao, T. M. (2013). J. Appl. Chem. 2, 722-729.]). In this context and as part of our continued investigations of N-(4-substitutedphen­yl)-4-bromo­benzene­sulfonamides (Vinola et al., 2015[Vinola, Z. R., Snehala, Naveen, S., Lokanath, N. K. & Suchetan, P. A. (2015). Der Pharma Chem. 7, 299-307.]), we report herein the crystal structure of N-(4-bromo­phen­yl)-4-bromo­benzene­sulfonamide.

The mol­ecule of the title compound (I) (Fig. 1[link]) is U shaped, the central segment having a C1—S1—N1—C7 torsion angle of 63.2 (4)°. Further, the dihedral angle between the benzene rings is 38.5 (2)°.

[Figure 1]
Figure 1
A view of the mol­ecular structure of the compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.

The crystal structure features strong N1—H1⋯O2 hydrogen bonds (Table 1[link]) that result in infinite [100] C(4) chains (Fig. 2[link]). Mol­ecules in adjacent chains are inter­linked via C9—H9⋯O1 inter­actions which run along the b axis, forming C(7) chains. This results in a two-dimensional network in the ab plane (Fig. 3[link]); adjacent networks are connected by short Br1⋯Br2 contacts [3.5092 (8) Å] propagating along the diagonal of the ac plane, so that a three-dimensional supra­molecular architecture ensues (Fig. 4[link]).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1⋯O2i 0.90 (3) 2.06 (2) 2.945 (5) 170 (5)
C9—H9⋯O1ii 0.93 2.48 3.238 (6) 138
Symmetry codes: (i) x-1, y, z; (ii) [-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}].
[Figure 2]
Figure 2
Crystal packing of the title compound, displaying the N—H⋯O chains running along [100].
[Figure 3]
Figure 3
Formation of a two-dimensional network in the ab plane via N—H⋯O hydrogen bonds and C—H⋯O inter­actions.
[Figure 4]
Figure 4
The three-dimensional architecture in the crystal structure.

The dihedral angle between the benzene rings in 4-bromo-N-(4-nitro­phen­yl)-benzene­sulfonamide (II) (Vinola et al., 2015[Vinola, Z. R., Snehala, Naveen, S., Lokanath, N. K. & Suchetan, P. A. (2015). Der Pharma Chem. 7, 299-307.]) is slightly less than that in (I), being 32.6 (6)°. The central segment C1—S1—N1—C7 has a torsion angle of −64.2 (3)° in (II), compared to 63.2 (4)° in (I). Similar to (I), the crystal structure of (II) displays a three-dimensional architecture. A structure-directing N—H⋯O hydrogen bond and three different structure-directing C—H⋯O inter­actions along with weak C—Br⋯O inter­actions, consolidate the crystal structure of (II) into a three dimensional architecture.

Synthesis and crystallization

Compound (I) was prepared according to the literature method (Vinola et al., 2015[Vinola, Z. R., Snehala, Naveen, S., Lokanath, N. K. & Suchetan, P. A. (2015). Der Pharma Chem. 7, 299-307.]). The purity of the compound was checked by determining its melting point. Prismatic single crystals of (I) suitable for X-ray diffraction study were obtained by slow evaporation of an ethano­lic solution of (I) at room temperature.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link]. To improve considerably the values of R1, wR2, and GOOF, the bad (132), (105) and (024) reflections were omitted from the final refinement.

Table 2
Experimental details

Crystal data
Chemical formula C12H9Br2NO2S
Mr 391.08
Crystal system, space group Monoclinic, P21/n
Temperature (K) 296
a, b, c (Å) 5.0643 (3), 12.8006 (7), 20.5540 (11)
β (°) 91.076 (2)
V (Å3) 1332.20 (13)
Z 4
Radiation type Cu Kα
μ (mm−1) 9.14
Crystal size (mm) 0.28 × 0.27 × 0.22
 
Data collection
Diffractometer Bruker APEXII
Absorption correction Multi-scan (SADABS; Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.])
Tmin, Tmax 0.184, 0.238
No. of measured, independent and observed [I > 2σ(I)] reflections 9589, 2142, 2092
Rint 0.050
(sin θ/λ)max (Å−1) 0.585
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.061, 0.181, 1.16
No. of reflections 2142
No. of parameters 167
No. of restraints 1
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 1.15, −1.26
Computer programs: APEX2, SAINT-Plus and XPREP (Bruker, 2009[Bruker (2009). APEX2, SADABS, SAINT-Plus and XPREP. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97 and SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]).

Structural data

CCDC reference: 1474176

Crystal structure: contains datablock I. DOI: 10.1107/S2414314616006313/zq4006sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616006313/zq4006Isup2.hkl

Supporting information file. DOI: 10.1107/S2414314616006313/zq4006Isup3.cml

checkCIF report


Introduction top

Sulfonamide drugs were the first among the chemotherapeutic agents to be used for curing and prevention of bacterial infection in human beings (Shiva Prasad et al., 2011). They play a vital role as a key constituent in a number of biologically active molecules. Till date, sulfonamides have been known to exhibit a wide variety of biological activities such as anti­bacterial (Subhakara Reddy et al., 2012), insecticidal (Chester Himel et al., 1971), anti­fungal (Hanafy et al., 2007), anti­hepatitis (Yan-Fang et al., 2010), anti­inflamatory (Kuçukguzel et al., 2013), anti­tumor (Ghorab et al., 2011), anti­cancer (Al Said et al., 2011), anti-HIV (Sahu et al., 2007) and anti­tubercular activities (Vora et al., 2012). In recent years, extensive research studies have been carried out on the synthesis and evaluation of pharmacological activities of molecules containing sulfonamide moiety for different activities, and have been reported to be as important pharmacophores (Mohan et al., 2013). Keeping the above things in mind and in our continued efforts for understanding the structures of N-(4-substitutedphenyl)-4-bromo­benzene­sulfonamides (Vinola et al., 2015), we report herein the crystal structure of N-(4-bromo­phenyl)-4-bromo­benzene­sulfonamide (I).

Experimental top

Synthesis and crystallization top

Compound (I) was prepared according to the literature method (Vinola et al., 2015). The purity of the compound was checked by determining its melting point. Prism like single crystals of (I) used for X-ray diffraction study were obtained by slow evaporation of the ethano­lic solution of (I) at room temperature.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 1. The H atom of the NH group was located in a difference map and and later restained to N—H = 0.90 (1) Å. Positions of hydrogen atoms bonded to carbon atoms were generated in idealized geometries using a riding model with C—H = 0.93 Å and their displacement parameters were set to Uiso(H) = 1.2 Ueq(C). To improve considerably the values of R1, wR2, and GOOF, the bad (132), (105) & (024) reflection was omitted from the final refinement of (I).

Results and discussion top

Experimental top

Compound (I) was prepared according to the literature method (Vinola et al., 2015). The purity of the compound was checked by determining its melting point. Prismatic single crystals of (I) suitable for X-ray diffraction study were obtained by slow evaporation of an ethanolic solution of (I) at room temperature.

Refinement top

Crystal data, data collection and structure refinement details are summarized in Table 2. To improve considerably the values of R1, wR2, and GOOF, the bad (132), (105) and (024) reflections were omitted from the final refinement .

Structure description top

Sulfonamide drugs were the first chemotherapeutic agents to be used to cure and prevent bacterial infection in human beings (Shiva Prasad et al., 2011). They play a vital role as a key constituent in a number of biologically active molecules being known to exhibit a wide variety of biological activities such as antibacterial (Subhakara Reddy et al., 2012), insecticidal (Himel et al., 1971), antifungal (Hanafy et al., 2007), antihepatitis (Yan-Fang et al., 2010), anti-inflamatory (Küçükgüzel et al., 2013), antitumor (Ghorab et al., 2011), anticancer (Al-Said et al., 2011), anti-HIV (Sahu et al., 2007) and antitubercular activities (Vora et al., 2012). In recent years, extensive research has been carried out on the synthesis and evaluation of the pharmacological activities of molecules containing the sulfonamide moiety, and they have been reported to be as important pharmacophores (Mohan et al., 2013). In this context and as part of our continued investigations of N-(4-substitutedphenyl)-4-bromobenzenesulfonamides (Vinola et al., 2015), we report herein the crystal structure of N-(4-bromophenyl)-4-bromobenzenesulfonamide.

The molecule of the title compound (I) (Fig. 1) is U shaped, the central segment having a C1—S1—N1—C7 torsion angle of 63.2 (4)°. Further, the dihedral angle between the benzene rings is 38.5 (2)°.

The crystal structure features strong N1—H1···O2 hydrogen bonds that result in infinite [100] C(4) chains (Fig. 2). Molecules in adjacent chains are interlinked via C9—H9···O1 interactions which run along b axis, forming C(7) chains. This results in a two-dimensional network in the ab plane (Fig. 3); adjacent networks are connected by short Br1···Br2 contact [3.5092 (8) Å] propagating along the diagonal of the ac plane, so that a three-dimensional supramolecular architecture ensues (Fig. 4).

The dihedral angle between the benzene rings in 4-bromo-N-(4-nitrophenyl)-benzenesulfonamide (II) (Vinola et al., 2015) is slightly less than that in (I), being 32.6 (6)°. The central segment C1—S1—N1—C7 has a torsion angle of -64.2 (3)° in (II), compared to 63.2 (4)° in (I). Similar to (I), the crystal structure of (II) display a three-dimensional architecture. A structure-directing N—H···O hydrogen bond and three different structure-directing C—H···O interactions along with weak C—Br···O interactions consolidate the crystal structure of (II) into a three dimensional architechture.

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: APEX2 and SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus and XPREP (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. A view of the molecular structure of the compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. Crystal packing of the title compound, displaying the N—H···O chains running along [100].
[Figure 3] Fig. 3. Formation of a two-dimensional network in the ab plane via N—H···O hydrogen bonds and C—H···O interactions.
[Figure 4] Fig. 4. The three-dimensional architecture in the crystal structure .
4-Bromo-N-(4-bromophenyl)benzenesulfonamide top
Crystal data top
C12H9Br2NO2SPrism
Mr = 391.08Dx = 1.950 Mg m−3
Monoclinic, P21/nMelting point: 413 K
Hall symbol: -P 2ynCu Kα radiation, λ = 1.54178 Å
a = 5.0643 (3) ÅCell parameters from 167 reflections
b = 12.8006 (7) Åθ = 4.1–64.5°
c = 20.5540 (11) ŵ = 9.14 mm−1
β = 91.076 (2)°T = 296 K
V = 1332.20 (13) Å3Prism, colourless
Z = 40.28 × 0.27 × 0.22 mm
F(000) = 760
Data collection top
Bruker APEXII
diffractometer		2142 independent reflections
Radiation source: fine-focus sealed tube2092 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.050
Detector resolution: 1 pixels mm-1θmax = 64.5°, θmin = 4.1°
phi and φ scansh = −5→5
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		k = −14→14
Tmin = 0.184, Tmax = 0.238l = −23→23
9589 measured reflections
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.181H atoms treated by a mixture of independent and constrained refinement
S = 1.16 w = 1/[σ2(Fo2) + (0.1331P)2 + 1.7178P]
where P = (Fo2 + 2Fc2)/3
2142 reflections(Δ/σ)max < 0.001
167 parametersΔρmax = 1.15 e Å−3
1 restraintΔρmin = −1.26 e Å−3
Crystal data top
C12H9Br2NO2SV = 1332.20 (13) Å3
Mr = 391.08Z = 4
Monoclinic, P21/nCu Kα radiation
a = 5.0643 (3) ŵ = 9.14 mm−1
b = 12.8006 (7) ÅT = 296 K
c = 20.5540 (11) Å0.28 × 0.27 × 0.22 mm
β = 91.076 (2)°
Data collection top
Bruker APEXII
diffractometer		2142 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2009)		2092 reflections with I > 2σ(I)
Tmin = 0.184, Tmax = 0.238Rint = 0.050
9589 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0611 restraint
wR(F2) = 0.181H atoms treated by a mixture of independent and constrained refinement
S = 1.16Δρmax = 1.15 e Å−3
2142 reflectionsΔρmin = −1.26 e Å−3
167 parameters
Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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 (Å2) top
xyzUiso*/Ueq
C10.5612 (9)0.6558 (3)0.1853 (2)0.0144 (9)
C20.6912 (9)0.5603 (4)0.1886 (2)0.0212 (10)
H20.83160.55060.21780.025*
C30.6100 (11)0.4798 (4)0.1481 (3)0.0246 (11)
H30.69590.41570.14970.030*
C40.3999 (10)0.4956 (3)0.1053 (2)0.0195 (10)
C50.2722 (10)0.5905 (4)0.1016 (2)0.0225 (10)
H50.13300.59990.07200.027*
C60.3507 (10)0.6715 (4)0.1418 (2)0.0174 (10)
H60.26460.73560.13980.021*
C70.5220 (8)0.6491 (3)0.3422 (2)0.0122 (9)
C80.3527 (9)0.5641 (4)0.3350 (3)0.0227 (10)
H80.20890.56840.30630.027*
C90.3960 (10)0.4734 (4)0.3701 (3)0.0218 (10)
H90.28100.41720.36550.026*
C100.6108 (9)0.4672 (3)0.4119 (2)0.0187 (10)
C110.7797 (10)0.5524 (4)0.4209 (2)0.0230 (10)
H110.92240.54830.45000.028*
C120.7313 (10)0.6431 (4)0.3860 (2)0.0201 (10)
H120.84120.70060.39210.024*
N10.4784 (7)0.7427 (3)0.30503 (18)0.0142 (8)
O10.5684 (6)0.8555 (2)0.21164 (16)0.0192 (7)
O20.9253 (6)0.7423 (2)0.25806 (16)0.0189 (7)
S10.65243 (19)0.75847 (8)0.23895 (5)0.0125 (4)
Br10.28679 (13)0.38445 (4)0.05096 (3)0.0339 (3)
Br20.68273 (11)0.34108 (4)0.45686 (2)0.0271 (3)
H10.312 (4)0.751 (4)0.290 (2)0.010 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.015 (2)0.013 (2)0.016 (2)−0.0018 (16)0.0027 (17)0.0005 (16)
C20.023 (2)0.021 (2)0.019 (2)0.0029 (19)−0.0061 (18)−0.0004 (19)
C30.035 (3)0.017 (2)0.022 (3)0.0076 (19)−0.002 (2)−0.0035 (19)
C40.033 (3)0.015 (2)0.011 (2)−0.0025 (19)−0.0005 (18)−0.0009 (17)
C50.031 (3)0.019 (2)0.018 (3)0.0024 (19)−0.0083 (19)0.0000 (19)
C60.024 (2)0.016 (2)0.012 (2)0.0034 (17)−0.0042 (18)−0.0014 (16)
C70.010 (2)0.014 (2)0.013 (2)0.0003 (16)0.0024 (17)−0.0034 (16)
C80.019 (2)0.017 (2)0.032 (3)−0.0026 (18)−0.0089 (19)0.0001 (19)
C90.026 (2)0.013 (2)0.026 (3)−0.0046 (18)−0.0082 (19)−0.0004 (18)
C100.023 (2)0.014 (2)0.019 (2)0.0010 (17)0.0021 (18)−0.0022 (17)
C110.026 (2)0.025 (2)0.018 (2)−0.0054 (19)−0.0073 (19)0.0050 (19)
C120.028 (3)0.020 (2)0.012 (2)−0.0113 (19)−0.0055 (19)0.0026 (18)
N10.0108 (18)0.0145 (17)0.017 (2)0.0023 (13)−0.0016 (15)−0.0013 (15)
O10.0214 (17)0.0144 (15)0.0215 (18)−0.0005 (12)−0.0043 (13)0.0010 (13)
O20.0117 (15)0.0205 (15)0.0245 (18)−0.0008 (11)−0.0030 (12)−0.0001 (13)
S10.0116 (6)0.0123 (6)0.0135 (6)−0.0008 (3)−0.0022 (4)0.0006 (4)
Br10.0600 (5)0.0180 (5)0.0234 (5)0.0004 (2)−0.0122 (3)−0.00819 (19)
Br20.0410 (5)0.0172 (5)0.0228 (4)0.00183 (18)−0.0048 (3)0.00593 (18)
Geometric parameters (Å, º) top
C1—C21.389 (7)C7—N11.435 (6)
C1—C61.393 (7)C8—C91.382 (7)
C1—S11.772 (4)C8—H80.9300
C2—C31.381 (7)C9—C101.375 (7)
C2—H20.9300C9—H90.9300
C3—C41.382 (7)C10—C111.396 (7)
C3—H30.9300C10—Br21.892 (5)
C4—C51.377 (7)C11—C121.385 (7)
C4—Br11.892 (5)C11—H110.9300
C5—C61.380 (7)C12—H120.9300
C5—H50.9300N1—S11.646 (4)
C6—H60.9300N1—H10.895 (10)
C7—C121.380 (7)O1—S11.425 (3)
C7—C81.391 (6)O2—S11.445 (3)
C2—C1—C6121.0 (4)C7—C8—H8119.7
C2—C1—S1120.3 (4)C10—C9—C8119.4 (4)
C6—C1—S1118.7 (3)C10—C9—H9120.3
C3—C2—C1119.4 (4)C8—C9—H9120.3
C3—C2—H2120.3C9—C10—C11120.9 (4)
C1—C2—H2120.3C9—C10—Br2119.8 (3)
C2—C3—C4119.4 (4)C11—C10—Br2119.3 (4)
C2—C3—H3120.3C12—C11—C10118.9 (5)
C4—C3—H3120.3C12—C11—H11120.5
C5—C4—C3121.3 (4)C10—C11—H11120.5
C5—C4—Br1119.6 (4)C7—C12—C11120.8 (4)
C3—C4—Br1119.2 (4)C7—C12—H12119.6
C4—C5—C6120.0 (5)C11—C12—H12119.6
C4—C5—H5120.0C7—N1—S1117.5 (3)
C6—C5—H5120.0C7—N1—H1114 (3)
C5—C6—C1118.9 (4)S1—N1—H1103 (3)
C5—C6—H6120.5O1—S1—O2120.63 (19)
C1—C6—H6120.5O1—S1—N1105.77 (19)
C12—C7—C8119.3 (4)O2—S1—N1106.41 (19)
C12—C7—N1120.2 (4)O1—S1—C1109.2 (2)
C8—C7—N1120.5 (4)O2—S1—C1107.4 (2)
C9—C8—C7120.7 (4)N1—S1—C1106.58 (19)
C9—C8—H8119.7
C6—C1—C2—C3−0.1 (7)Br2—C10—C11—C12177.6 (4)
S1—C1—C2—C3177.3 (4)C8—C7—C12—C112.3 (7)
C1—C2—C3—C4−0.4 (7)N1—C7—C12—C11−178.4 (4)
C2—C3—C4—C50.9 (8)C10—C11—C12—C7−0.9 (7)
C2—C3—C4—Br1−179.1 (4)C12—C7—N1—S182.2 (5)
C3—C4—C5—C6−1.0 (8)C8—C7—N1—S1−98.5 (4)
Br1—C4—C5—C6179.0 (4)C7—N1—S1—O1179.3 (3)
C4—C5—C6—C10.5 (7)C7—N1—S1—O2−51.3 (4)
C2—C1—C6—C50.0 (7)C7—N1—S1—C163.2 (4)
S1—C1—C6—C5−177.5 (4)C2—C1—S1—O1158.4 (4)
C12—C7—C8—C9−1.5 (7)C6—C1—S1—O1−24.1 (4)
N1—C7—C8—C9179.2 (4)C2—C1—S1—O225.9 (4)
C7—C8—C9—C10−0.8 (8)C6—C1—S1—O2−156.6 (4)
C8—C9—C10—C112.3 (8)C2—C1—S1—N1−87.8 (4)
C8—C9—C10—Br2−176.8 (4)C6—C1—S1—N189.7 (4)
C9—C10—C11—C12−1.4 (7)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.90 (3)2.06 (2)2.945 (5)170 (5)
C9—H9···O1ii0.932.483.238 (6)138
Symmetry codes: (i) x−1, y, z; (ii) −x+1/2, y−1/2, −z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.90 (3)2.06 (2)2.945 (5)170 (5)
C9—H9···O1ii0.932.483.238 (6)138
Symmetry codes: (i) x−1, y, z; (ii) −x+1/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formulaC12H9Br2NO2S
Mr391.08
Crystal system, space groupMonoclinic, P21/n
Temperature (K)296
a, b, c (Å)5.0643 (3), 12.8006 (7), 20.5540 (11)
β (°) 91.076 (2)
V (Å3)1332.20 (13)
Z4
Radiation typeCu Kα
µ (mm−1)9.14
Crystal size (mm)0.28 × 0.27 × 0.22
Data collection
DiffractometerBruker APEXII
Absorption correctionMulti-scan
(SADABS; Bruker, 2009)
Tmin, Tmax0.184, 0.238
No. of measured, independent and
observed [I > 2σ(I)] reflections		9589, 2142, 2092
Rint0.050
(sin θ/λ)max (Å−1)0.585
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.061, 0.181, 1.16
No. of reflections2142
No. of parameters167
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)1.15, −1.26

Computer programs: APEX2 (Bruker, 2009), APEX2 and SAINT-Plus (Bruker, 2009), SAINT-Plus and XPREP (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008).

 

Acknowledgements

The authors are thankful to the Institution of Excellence, Vijnana Bhavana, University of Mysore, Mysore, for providing the single-crystal X-ray diffraction data. VZR is thankful to the University Grants Commission, Delhi, for financial assistance under its MRP scheme.

References

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ISSN: 2414-3146
Volume 1| Part 4| April 2016| x160631
doi:10.1107/S2414314616006313
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