N-Benzoyl-2-nitro­benzene­sulfonamide

Suchetan, P.A.; Foro, S.; Gowda, B.T.; Nirmala, B.

doi:10.1107/S1600536811055917

organic compounds

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ISSN: 2056-9890

Volume 68| Part 2| February 2012| Page o339

doi:10.1107/S1600536811055917

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N-Benzoyl-2-nitrobenzenesulfonamide

P. A. Suchetan,^a Sabine Foro,^b B. Thimme Gowda ^a ^* and B. Nirmala ^c

^aDepartment of Chemistry, Mangalore University, Mangalagangotri 574 199, Mangalore, India, ^bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287 Darmstadt, Germany, and ^cDepartment of Chemistry, University College of Science, Tumkur University, Tumkur 572 102, India
^*Correspondence e-mail: gowdabt@yahoo.com

(Received 19 December 2011; accepted 27 December 2011; online 11 January 2012)

In the title compound, C₁₃H₁₀N₂O₅S, the N—C bond in the C—SO₂—NH—C segment has gauche torsion angles with respect to the S=O bonds. The conformation between the N—H bond and the ortho-nitro group in the sulfonyl benzene ring is syn. The molecule is twisted at the S—N bond with a torsion angle of −63.4 (2)°. The sulfonyl benzene ring is tilted by 77.1 (1)° relative to the —SO₂—NH—C—O segment. The dihedral angle between the sulfonyl and the benzoyl benzene rings is 88.6 (1)°. In the crystal, pairs of N—H⋯O(S) hydrogen bonds link the molecules into inversion dimers, which are linked by weak C—H⋯O and C—H⋯π interactions along the b axis.

Related literature

For studies, including those by our group, on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bowes et al. (2003 ); Gowda et al. (2006 ), on N-(aryl)-methanesulfonamides, see: Jayalakshmi & Gowda (2004 ), on N-(aryl)-arylsulfonamides, see: Gowda et al. (2003 ), on N-(substitutedbenzoyl)-arylsulfonamides, see: Suchetan et al. (2010 ) and on N-chloroarylamides, see: Gowda & Mahadevappa (1983 ).

Experimental

Crystal data

C₁₃H₁₀N₂O₅S
M_r = 306.29
Orthorhombic, P b c a
a = 12.1127 (8) Å
b = 11.7625 (8) Å
c = 18.730 (1) Å
V = 2668.6 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.27 mm⁻¹
T = 293 K
0.48 × 0.44 × 0.40 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.883, T_max = 0.901
6396 measured reflections
2711 independent reflections
2010 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.110
S = 1.04
2711 reflections
193 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.36 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C8–C13 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2ⁱ	0.84 (2)	2.21 (2)	3.003 (3)	158 (2)
C11—H11⋯O3ⁱⁱ	0.93	2.51	3.267 (3)	139
C13—H13⋯O2ⁱ	0.93	2.53	3.313 (3)	142
C6—H6⋯Cg1ⁱⁱⁱ	0.93	2.82	3.678 (13)	153
Symmetry codes: (i) -x+2, -y, -z+1; (ii) $[-x+{\script{5\over 2}}, y-{\script{1\over 2}}, z]$ ; (iii) $[-x+2, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811055917/bq2330sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811055917/bq2330Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811055917/bq2330Isup3.cml

checkCIF report

Comment top

Diaryl acylsulfonamides are known as potent antitumor agents against a broad spectrum of human tumor xenografts in nude mice. As part of our studies on the substituent effects on the structures and other aspects of N-(aryl)-amides (Bowes et al., 2003; Gowda et al., 2006), N-(aryl)-methanesulfonamides (Jayalakshmi & Gowda, 2004), N-(aryl)-arylsulfonamides (Gowda et al., 2003); N-(substitutedbenzoyl)-arylsulfonamides (Suchetan et al., 2010) and N-chloro-arylsulfonamides (Gowda & Mahadevappa, 1983), in the present work, the crystal structure of N-(benzoyl)- 2-nitrobenzenesulfonamide (I) has been determined (Fig.1).

In (I), the conformation between the N—H and C=O bonds in the C—SO₂—NH—C(O) segment is anti (Fig.1), similar to that observed in N-(benzoyl)-2-methylbenzenesulfonamide (II) (Suchetan et al., 2010). Furthermore, the N—C bond in the segment has gauche torsion with respect to the S═O bonds, while, the conformation between the N—H bond and the ortho-nitro group in the sulfonyl benzene ring is syn.

The molecule is twisted at the S—N bond with the torsional angle of -63.39 (22)°, compared to the value of 68.8 (4)° in (II).

The dihedral angle between the sulfonyl benzene ring and the —SO₂—NH—C—O segment is 77.1 (1)°, compared to the value of 84.8 (1)° in (II). Further, the dihedral angle between the sulfonyl and the benzoyl benzene rings is 88.6 (1)°, compared to the value of 73.9 (1)° in (II).

In the crystal, intermolecular N1–H1N···O2 and C13—H13···O2 hydrogen bonds link the molecules as dimers and these dimers are also linked by C11—H11···O3 hydrogen bonds and C—H···π interactions along b-axis (Table 1). [C6—H6···Cg1, cg1 is the centroid of C8—C13 ring] Parts of the crystal structure are shown in Fig. 2., Fig. 3. and Fig. 4.

Related literature top

For studies, including those by our group, on the effects of substituents on the structures and other aspects of N-(aryl)-amides, see: Bowes et al. (2003); Gowda et al. (2006), on N-(aryl)-methanesulfonamides, see: Jayalakshmi & Gowda (2004), on N-(aryl)-arylsulfonamides, see: Gowda et al. (2003), on N-(substitutedbenzoyl)-arylsulfonamides, see: Suchetan et al. (2010) and on N-chloroarylamides, see: Gowda & Mahadevappa (1983).

Experimental top

The title compound was prepared by refluxing a mixture of benzoic acid (0.02 mole), 2-nitrobenzenesulfonamide (0.02 mole) and excess phosphorous oxy chloride for 3 h on a water bath. The resultant mixture was cooled and poured into crushed ice. The solid, N-(benzoyl)-2-nitrobenzenesulfonamide, obtained was filtered, washed thoroughly with water and then dissolved in sodium bicarbonate solution. The compound was later reprecipitated by acidifying the filtered solution with dilute HCl. It was filtered, dried and recrystallized.

Prism like colourless single crystals of the title compound used in X-ray diffraction studies were obtained by slow evaporation of its toluene solution at room temperature.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound, showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Part of the crystal structure of the title compound, showing the dimers formed by N-H···O and C-H..O hydrogen bonds. [Symmetry code: (i) 2-x, -y, 1-z]
	Fig. 3. Part of the crystal structure of the title compound, showing the linking of the dimers by C-H···O hydrogen bonds along to the [010] direction. For the sake of clarity, H atoms not involved in the motif shown have been omitted. [Symmetry code: (ii) = 5/2-x, y-1/2, z]
	Fig. 4. Part of the crystal structure of the title compound, showing the formation of a chain along [010] generated by the C-H···π interactions. [Symmetry code: (iii) = 2-x, y+1/2, -z+1/2]

N-Benzoyl-2-nitrobenzenesulfonamide top

Crystal data top

C₁₃H₁₀N₂O₅S	F(000) = 1264
M_r = 306.29	D_x = 1.525 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2597 reflections
a = 12.1127 (8) Å	θ = 2.6–27.8°
b = 11.7625 (8) Å	µ = 0.27 mm⁻¹
c = 18.730 (1) Å	T = 293 K
V = 2668.6 (3) Å³	Prism, colorless
Z = 8	0.48 × 0.44 × 0.40 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2711 independent reflections
Radiation source: fine-focus sealed tube	2010 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
Rotation method data acquisition using ω scans	θ_max = 26.4°, θ_min = 2.7°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −13→15
T_min = 0.883, T_max = 0.901	k = −14→14
6396 measured reflections	l = −14→23

Refinement top

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0388P)² + 2.8009P] where P = (F_o² + 2F_c²)/3
2711 reflections	(Δ/σ)_max = 0.001
193 parameters	Δρ_max = 0.31 e Å⁻³
1 restraint	Δρ_min = −0.36 e Å⁻³

Crystal data top

C₁₃H₁₀N₂O₅S	V = 2668.6 (3) Å³
M_r = 306.29	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 12.1127 (8) Å	µ = 0.27 mm⁻¹
b = 11.7625 (8) Å	T = 293 K
c = 18.730 (1) Å	0.48 × 0.44 × 0.40 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2711 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	2010 reflections with I > 2σ(I)
T_min = 0.883, T_max = 0.901	R_int = 0.020
6396 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	1 restraint
wR(F²) = 0.110	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.31 e Å⁻³
2711 reflections	Δρ_min = −0.36 e Å⁻³
193 parameters

Special details top

Experimental. CrysAlis RED (Oxford Diffraction, 2009) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	1.01092 (19)	0.2867 (2)	0.42850 (12)	0.0320 (5)
C2	1.08964 (19)	0.3142 (2)	0.47986 (13)	0.0352 (5)
C3	1.1400 (2)	0.4186 (2)	0.48146 (15)	0.0458 (6)
H3	1.1912	0.4360	0.5168	0.055*
C4	1.1134 (2)	0.4975 (2)	0.42959 (15)	0.0503 (7)
H4	1.1473	0.5684	0.4298	0.060*
C5	1.0369 (2)	0.4717 (2)	0.37750 (15)	0.0496 (7)
H5	1.0201	0.5249	0.3424	0.060*
C6	0.9851 (2)	0.3670 (2)	0.37733 (14)	0.0413 (6)
H6	0.9326	0.3505	0.3426	0.050*
C7	1.0522 (2)	0.0708 (2)	0.31993 (13)	0.0344 (5)
C8	1.13311 (19)	−0.01632 (19)	0.29607 (12)	0.0332 (5)
C9	1.2011 (2)	0.0112 (2)	0.23910 (13)	0.0400 (6)
H9	1.1942	0.0816	0.2170	0.048*
C10	1.2786 (2)	−0.0652 (2)	0.21516 (14)	0.0436 (6)
H10	1.3247	−0.0458	0.1773	0.052*
C11	1.2882 (2)	−0.1697 (2)	0.24688 (14)	0.0482 (7)
H11	1.3412	−0.2209	0.2309	0.058*
C12	1.2194 (3)	−0.1986 (2)	0.30227 (16)	0.0589 (8)
H12	1.2252	−0.2701	0.3231	0.071*
C13	1.1419 (2)	−0.1227 (2)	0.32734 (14)	0.0482 (7)
H13	1.0959	−0.1428	0.3650	0.058*
N1	1.01881 (17)	0.06273 (17)	0.39120 (11)	0.0355 (5)
H1N	1.051 (2)	0.021 (2)	0.4206 (12)	0.043*
N2	1.12183 (18)	0.2319 (2)	0.53570 (13)	0.0467 (6)
O1	0.84056 (14)	0.17061 (15)	0.38774 (10)	0.0455 (5)
O2	0.92831 (15)	0.11935 (15)	0.50171 (9)	0.0418 (4)
O3	1.01759 (16)	0.14595 (15)	0.28213 (9)	0.0468 (5)
O4	1.09678 (19)	0.2545 (2)	0.59685 (11)	0.0660 (6)
O5	1.1726 (2)	0.14835 (19)	0.51681 (13)	0.0695 (6)
S1	0.93749 (5)	0.15669 (5)	0.42926 (3)	0.03293 (17)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0320 (11)	0.0317 (12)	0.0323 (12)	0.0037 (10)	0.0015 (10)	0.0001 (10)
C2	0.0327 (12)	0.0375 (13)	0.0355 (12)	0.0042 (10)	−0.0013 (10)	0.0035 (10)
C3	0.0393 (14)	0.0489 (16)	0.0492 (15)	−0.0016 (13)	−0.0060 (12)	−0.0019 (13)
C4	0.0541 (16)	0.0358 (14)	0.0612 (17)	−0.0060 (13)	0.0042 (15)	0.0024 (13)
C5	0.0635 (18)	0.0386 (15)	0.0468 (15)	0.0050 (14)	−0.0012 (14)	0.0098 (12)
C6	0.0469 (14)	0.0410 (14)	0.0360 (13)	0.0046 (12)	−0.0051 (12)	0.0010 (11)
C7	0.0372 (13)	0.0313 (12)	0.0347 (12)	−0.0031 (11)	0.0015 (11)	−0.0029 (10)
C8	0.0365 (12)	0.0312 (12)	0.0317 (12)	−0.0033 (11)	0.0017 (10)	−0.0058 (10)
C9	0.0483 (14)	0.0309 (12)	0.0408 (14)	−0.0057 (11)	0.0069 (12)	−0.0018 (11)
C10	0.0445 (15)	0.0418 (14)	0.0444 (14)	−0.0036 (12)	0.0145 (12)	−0.0040 (12)
C11	0.0536 (16)	0.0444 (15)	0.0465 (15)	0.0130 (13)	0.0086 (13)	−0.0081 (13)
C12	0.087 (2)	0.0385 (15)	0.0512 (16)	0.0179 (16)	0.0180 (16)	0.0066 (13)
C13	0.0654 (18)	0.0397 (14)	0.0395 (14)	0.0059 (14)	0.0193 (13)	0.0026 (12)
N1	0.0412 (12)	0.0330 (11)	0.0324 (11)	0.0076 (9)	0.0019 (9)	0.0004 (9)
N2	0.0417 (12)	0.0494 (14)	0.0490 (14)	0.0001 (11)	−0.0116 (11)	0.0062 (11)
O1	0.0335 (9)	0.0494 (11)	0.0535 (11)	0.0024 (8)	−0.0053 (8)	−0.0030 (9)
O2	0.0489 (10)	0.0402 (10)	0.0361 (9)	0.0012 (8)	0.0105 (8)	0.0004 (8)
O3	0.0561 (11)	0.0424 (10)	0.0420 (10)	0.0097 (9)	0.0068 (9)	0.0063 (9)
O4	0.0764 (15)	0.0815 (16)	0.0400 (12)	−0.0017 (13)	−0.0101 (11)	0.0097 (11)
O5	0.0756 (15)	0.0536 (13)	0.0794 (15)	0.0219 (12)	−0.0179 (13)	0.0069 (12)
S1	0.0321 (3)	0.0332 (3)	0.0335 (3)	0.0027 (3)	0.0028 (3)	−0.0015 (2)

Geometric parameters (Å, º) top

C1—C6	1.381 (3)	C8—C13	1.386 (3)
C1—C2	1.392 (3)	C9—C10	1.375 (3)
C1—S1	1.769 (2)	C9—H9	0.9300
C2—C3	1.372 (4)	C10—C11	1.370 (4)
C2—N2	1.477 (3)	C10—H10	0.9300
C3—C4	1.382 (4)	C11—C12	1.374 (4)
C3—H3	0.9300	C11—H11	0.9300
C4—C5	1.379 (4)	C12—C13	1.377 (4)
C4—H4	0.9300	C12—H12	0.9300
C5—C6	1.382 (4)	C13—H13	0.9300
C5—H5	0.9300	N1—S1	1.643 (2)
C6—H6	0.9300	N1—H1N	0.835 (17)
C7—O3	1.207 (3)	N2—O5	1.211 (3)
C7—N1	1.398 (3)	N2—O4	1.214 (3)
C7—C8	1.487 (3)	O1—S1	1.4177 (18)
C8—C9	1.386 (3)	O2—S1	1.4308 (17)

C6—C1—C2	118.4 (2)	C8—C9—H9	119.8
C6—C1—S1	118.86 (19)	C11—C10—C9	120.2 (2)
C2—C1—S1	122.61 (18)	C11—C10—H10	119.9
C3—C2—C1	121.8 (2)	C9—C10—H10	119.9
C3—C2—N2	117.0 (2)	C10—C11—C12	119.9 (2)
C1—C2—N2	121.2 (2)	C10—C11—H11	120.1
C2—C3—C4	118.8 (3)	C12—C11—H11	120.1
C2—C3—H3	120.6	C11—C12—C13	120.7 (3)
C4—C3—H3	120.6	C11—C12—H12	119.7
C5—C4—C3	120.4 (3)	C13—C12—H12	119.7
C5—C4—H4	119.8	C12—C13—C8	119.6 (2)
C3—C4—H4	119.8	C12—C13—H13	120.2
C4—C5—C6	120.2 (3)	C8—C13—H13	120.2
C4—C5—H5	119.9	C7—N1—S1	122.79 (17)
C6—C5—H5	119.9	C7—N1—H1N	122.4 (18)
C1—C6—C5	120.3 (2)	S1—N1—H1N	112.9 (18)
C1—C6—H6	119.8	O5—N2—O4	125.5 (2)
C5—C6—H6	119.8	O5—N2—C2	117.3 (2)
O3—C7—N1	120.7 (2)	O4—N2—C2	117.3 (2)
O3—C7—C8	123.8 (2)	O1—S1—O2	119.43 (11)
N1—C7—C8	115.5 (2)	O1—S1—N1	109.64 (11)
C9—C8—C13	119.4 (2)	O2—S1—N1	104.57 (10)
C9—C8—C7	117.5 (2)	O1—S1—C1	108.18 (11)
C13—C8—C7	123.1 (2)	O2—S1—C1	108.18 (11)
C10—C9—C8	120.3 (2)	N1—S1—C1	106.06 (11)
C10—C9—H9	119.8

C6—C1—C2—C3	1.2 (4)	C10—C11—C12—C13	−1.2 (5)
S1—C1—C2—C3	−175.2 (2)	C11—C12—C13—C8	0.3 (5)
C6—C1—C2—N2	−179.4 (2)	C9—C8—C13—C12	1.2 (4)
S1—C1—C2—N2	4.2 (3)	C7—C8—C13—C12	−179.8 (3)
C1—C2—C3—C4	−1.5 (4)	O3—C7—N1—S1	−3.5 (3)
N2—C2—C3—C4	179.1 (2)	C8—C7—N1—S1	175.16 (16)
C2—C3—C4—C5	0.4 (4)	C3—C2—N2—O5	−112.1 (3)
C3—C4—C5—C6	0.8 (4)	C1—C2—N2—O5	68.4 (3)
C2—C1—C6—C5	0.1 (4)	C3—C2—N2—O4	66.7 (3)
S1—C1—C6—C5	176.7 (2)	C1—C2—N2—O4	−112.7 (3)
C4—C5—C6—C1	−1.1 (4)	C7—N1—S1—O1	53.2 (2)
O3—C7—C8—C9	23.9 (4)	C7—N1—S1—O2	−177.62 (19)
N1—C7—C8—C9	−154.7 (2)	C7—N1—S1—C1	−63.4 (2)
O3—C7—C8—C13	−155.1 (3)	C6—C1—S1—O1	−16.5 (2)
N1—C7—C8—C13	26.2 (3)	C2—C1—S1—O1	159.83 (19)
C13—C8—C9—C10	−1.8 (4)	C6—C1—S1—O2	−147.3 (2)
C7—C8—C9—C10	179.1 (2)	C2—C1—S1—O2	29.1 (2)
C8—C9—C10—C11	0.9 (4)	C6—C1—S1—N1	101.0 (2)
C9—C10—C11—C12	0.7 (4)	C2—C1—S1—N1	−82.6 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C8–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.84 (2)	2.21 (2)	3.003 (3)	158 (2)
C11—H11···O3ⁱⁱ	0.93	2.51	3.267 (3)	139
C13—H13···O2ⁱ	0.93	2.53	3.313 (3)	142
C6—H6···Cg1ⁱⁱⁱ	0.93	2.82	3.678 (13)	153

Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+5/2, y−1/2, z; (iii) −x+2, y+1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₃H₁₀N₂O₅S
M_r	306.29
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	12.1127 (8), 11.7625 (8), 18.730 (1)
V (Å³)	2668.6 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.48 × 0.44 × 0.40

Data collection
Diffractometer	Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.883, 0.901
No. of measured, independent and observed [I > 2σ(I)] reflections	6396, 2711, 2010
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.043, 0.110, 1.04
No. of reflections	2711
No. of parameters	193
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.36

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C8–C13 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2ⁱ	0.835 (17)	2.214 (19)	3.003 (3)	158 (2)
C11—H11···O3ⁱⁱ	0.93	2.51	3.267 (3)	138.8
C13—H13···O2ⁱ	0.93	2.53	3.313 (3)	142.3
C6—H6···Cg1ⁱⁱⁱ	0.93	2.82	3.678 (13)	153.3

Symmetry codes: (i) −x+2, −y, −z+1; (ii) −x+5/2, y−1/2, z; (iii) −x+2, y+1/2, −z+1/2.

Acknowledgements

BTG thanks the University Grants Commission, Government of India, New Delhi, for a special grant under the UGC–BSR one-time grant to faculty.

References

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Volume 68| Part 2| February 2012| Page o339

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