N-[(2-Chloro­phen­yl)sulfon­yl]-2-meth­oxy­benzamide

Sreenivasa, S.; Palakshamurthy, B.S.; Suresha, E.; Tonannavar, J.; Jayashree, Y.; Suchetan, P.A.

doi:10.1107/S1600536813029012

organic compounds

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ISSN: 2056-9890

Volume 69| Part 11| November 2013| Page o1716

doi:10.1107/S1600536813029012

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N-[(2-Chlorophenyl)sulfonyl]-2-methoxybenzamide

S. Sreenivasa,^a B. S. Palakshamurthy,^b E Suresha,^c J. Tonannavar,^d Yenagi Jayashree ^d and P. A. Suchetan ^e ^*

^aDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India, ^bDepartment of Studies and Research in Physics, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India, ^cUniversity College of Science, Tumkur University, Tumkur 572 103, Karnataka, India, ^dDepartment of Physics, Karnatak University, Dharwad, Karnataka 580 003, India, and ^eDepartment of Studies and Research in Chemistry, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India
^*Correspondence e-mail: pasuchetan@yahoo.co.in

(Received 16 October 2013; accepted 22 October 2013; online 31 October 2013)

The title compound, C₁₄H₁₂ClNO₄S, crystallizes with two molecules in the asymmetric unit. The dihedral angles between the benzene rings are 89.68 (1) (molecule 1) and 82.9 (1)° (molecule 2). In each molecule, intramolecular N—H⋯O hydrogen bonds between the amide H atom and the methoxy O atom generate S(6) loops. In the crystal, molecule 2 is linked into inversion dimers through pairs of C—H⋯O interactions, forming an R₂²(8) ring motif. Molecules 1 and 2 are further linked along the b-axis direction through C—H⋯π interactions. The crystal structure is further stabilized by several π–π stacking interactions [centroid–centroid separations = 3.7793 (1), 3.6697 (1) and 3.6958 (1) Å], thus generating a three-dimensional architecture.

CCDC reference: 967734

Related literature

For similar structures, see: Gowda et al. (2010 ); Suchetan et al. (2010a ,b , 2013 ). For hydrogen-bond motifs see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₄H₁₂ClNO₄S
M_r = 325.76
Triclinic, $[P \overline 1]$
a = 8.0508 (3) Å
b = 12.9487 (4) Å
c = 14.1915 (5) Å
α = 83.897 (2)°
β = 89.368 (2)°
γ = 89.704 (2)°
V = 1470.94 (9) Å³
Z = 4
Mo Kα radiation
μ = 0.42 mm⁻¹
T = 293 K
0.36 × 0.29 × 0.23 mm

Data collection

Bruker APEXII CCD diffractometer
34023 measured reflections
9760 independent reflections
6518 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.163
S = 0.90
9760 reflections
389 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.68 e Å⁻³
Δρ_min = −0.59 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C22–C27 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—HN1⋯O4	0.84 (2)	1.97 (2)	2.625 (2)	135 (2)
N2—HN2⋯O8	0.83 (2)	1.99 (2)	2.629 (3)	133 (2)
C13—H13⋯O3ⁱ	0.93	2.50	3.292 (3)	143
C10—H10⋯Cg	0.93	2.85	3.729 (3)	157
Symmetry code: (i) -x+1, -y+2, -z+1.

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.

Supporting information

CCDC reference: 967734

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: 10.1107/S1600536813029012/sj5359sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813029012/sj5359Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813029012/sj5359Isup3.cml

checkCIF report

Comment top

As a part of our continued efforts to study the crystal structures of N-(aroyl)-arylsulfonamides (Suchetan et al., 2010a,b,2013), we report here the crystal structure of the title compound (I) (Fig 1).

The title compound (I) crystallizes with two molecules in the asymmetric unit. This is in contrast to the single molecules observed in the asymmetric units of N-(benzoyl)-2-chloro-benzenesulfonamide (II) (Gowda et al., 2010), N-(2-chlorobenzoyl)-2-chloro-benzenesulfonamide (III) (Suchetan et al., 2010a), N-(2-methylbenzoyl)-2-chloro-benzenesulfonamide (IV) (Suchetan et al., 2010b) and N-(3-methoxybenzoyl)-2-chloro-benzenesulfonamide (V) (Suchetan et al., 2013). In the compound, the conformation of the N—H bond in the C—SO₂—NH—C(O) segment is anti to the C=O bond. The dihedral angles between the two benzene rings in (I) are 89.68 (1)° (molecule 1) and 82.9 (1)° (molecule 2). Compared to this, the dihedral angles are 73.3 (1)° in II (Gowda et al., 2010), 76.9 (1)° in III (Suchetan et al., 2010a), 78.7 (1)° in IV (Suchetan et al., 2010b) and 87.4 (1)° in V (Suchetan et al., 2013). The conformation of the N—H bond is syn to both the o-chloro and o-methoxy substituents in (I), similar to that observed in V (Suchetan et al., 2013). However, in III (Suchetan et al., 2010a) and IV (Suchetan et al., 2010b) the opposite effect is observed i.e., the N—H bond is anti to both the o-chloro and o-methoxy substituents. In both molecules, intramolecular N1—HN1···O4 and N2—HN2···O8 hydrogen bonds between the amide H atoms and the methoxy O atoms, generate S(6) loops (Bernstein et al., 1995)(Fig 2).

In the crystal, molecule 2 is linked into inversion dimers through intermolecular C13—H13···O3 (Fig 3) interactions forming an R₂²(8) ring motif (Bernstein et al., 1995). Molecule 1 and 2 are further linked through C10—H10···π interactions along the b axis (Fig 4). The crystal structure is further stabilized by several π -π interactions [centroid-centroid separation being 3.7793 (1) Å (for Cg1—Cg1), 3.6697 (1) Å (for Cg3—Cg3) and 3.6958 (1) Å (for Cg2—Cg2)] (Fig 5). Cg1 and Cg3 are the centroids of the C8···C13 and C22···C27 methoxy benzene rings and Cg2 is the centroid of the C1···C6 sulfonamide ring.

Related literature top

For similar structures, see: Gowda et al. (2010); Suchetan et al. (2010a,b, 2013). For hydrogen-bond motifs see: Bernstein et al. (1995).

Experimental top

The title compound was prepared by refluxing a mixture of 2-methoxybenzoic acid, 2-chlorobenzene sulfonamide and phosphorous oxychloride for 2 h on a water bath. The resulting mixture was cooled and poured into ice cold water. The Solid obtained was filtered and washed thoroughly with water and then dissolved in sodium bicarbonate solution. The compound was later reprecipitated by acidifying the filtered solution with dilute HCl. The filtered and dried solid was recrystallized to the constant melting point (429 K). Colorless prisms of (I) were obtained from a slow evaporation of an ethanolic solution at room temperature.

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

	Fig. 1. Molecular structure of the title compound, showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Formation of intramolecular N—H···O hydrogen bonds, dashed lines, generating S(6) loops.
	Fig. 3. Packing of molecules in I through intermolecular C—H···O interactions, dashed lines, generating R₂²(8) loops. H atoms not involved in H-bonding are ommitted for clarity.
	Fig. 4. Linking of molecules along b axis in (I) through C—H···Cg1 interactions. H atoms not involved in H-bonding are ommitted for clarity.
	Fig. 5. Stacking of molecules in I, through Cg···Cg interactions. Where Cg1 and Cg3 are the centroids of the C8—C13 and C22—C27 methoxy benzene rings and Cg2 is the centroid of the C1—C6 sulfonamide ring. H atoms are ommitted for clarity.

N-[(2-Chlorophenyl)sulfonyl]-2-methoxybenzamide top

Crystal data top

C₁₄H₁₂ClNO₄S	F(000) = 672
M_r = 325.76	Prism
Triclinic, P1	D_x = 1.471 Mg m⁻³
Hall symbol: -P 1	Melting point: 429 K
a = 8.0508 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.9487 (4) Å	Cell parameters from 1234 reflections
c = 14.1915 (5) Å	θ = 1.6–31.8°
α = 83.897 (2)°	µ = 0.42 mm⁻¹
β = 89.368 (2)°	T = 293 K
γ = 89.704 (2)°	Prism, colourless
V = 1470.94 (9) Å³	0.36 × 0.29 × 0.23 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	6518 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.028
Graphite monochromator	θ_max = 31.8°, θ_min = 1.6°
ϕ and ω scans	h = −11→11
34023 measured reflections	k = −17→19
9760 independent reflections	l = −20→20

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.163	H atoms treated by a mixture of independent and constrained refinement
S = 0.90	w = 1/[σ²(F_o²) + (0.0876P)² + 0.587P] where P = (F_o² + 2F_c²)/3
9760 reflections	(Δ/σ)_max = 0.002
389 parameters	Δρ_max = 0.68 e Å⁻³
0 restraints	Δρ_min = −0.59 e Å⁻³

Crystal data top

C₁₄H₁₂ClNO₄S	γ = 89.704 (2)°
M_r = 325.76	V = 1470.94 (9) Å³
Triclinic, P1	Z = 4
a = 8.0508 (3) Å	Mo Kα radiation
b = 12.9487 (4) Å	µ = 0.42 mm⁻¹
c = 14.1915 (5) Å	T = 293 K
α = 83.897 (2)°	0.36 × 0.29 × 0.23 mm
β = 89.368 (2)°

Data collection top

Bruker APEXII CCD diffractometer	6518 reflections with I > 2σ(I)
34023 measured reflections	R_int = 0.028
9760 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.163	H atoms treated by a mixture of independent and constrained refinement
S = 0.90	Δρ_max = 0.68 e Å⁻³
9760 reflections	Δρ_min = −0.59 e Å⁻³
389 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

	x	y	z	U_iso*/U_eq
C28	−0.6577 (5)	1.3256 (3)	0.3153 (3)	0.1291 (16)
H28A	−0.6248	1.2553	0.3352	0.194*
H28B	−0.6856	1.3319	0.2494	0.194*
H28C	−0.7526	1.3435	0.3519	0.194*
HN2	−0.408 (3)	1.5138 (18)	0.2590 (15)	0.057 (6)*
HN1	0.080 (3)	1.0299 (18)	0.2691 (15)	0.056 (6)*
C1	0.4099 (2)	1.01693 (13)	0.14113 (11)	0.0413 (3)
C2	0.3854 (3)	1.11730 (15)	0.09867 (13)	0.0526 (4)
C3	0.5167 (3)	1.17506 (18)	0.05849 (16)	0.0692 (6)
H3	0.4993	1.2427	0.0311	0.083*
C4	0.6705 (4)	1.1329 (2)	0.05921 (16)	0.0732 (7)
H4	0.7584	1.1720	0.0317	0.088*
C5	0.7001 (3)	1.0329 (2)	0.09992 (17)	0.0696 (7)
H5	0.8066	1.0047	0.0995	0.084*
C6	0.5675 (2)	0.97436 (17)	0.14195 (14)	0.0533 (4)
H6	0.5857	0.9072	0.1702	0.064*
C7	0.2633 (3)	1.02032 (16)	0.35657 (13)	0.0504 (4)
C8	0.1764 (2)	1.07678 (14)	0.42977 (12)	0.0476 (4)
C9	0.0234 (3)	1.12861 (14)	0.41869 (13)	0.0520 (4)
C10	−0.0391 (3)	1.18159 (17)	0.49168 (16)	0.0654 (6)
H10	−0.1393	1.2174	0.4840	0.078*
C11	0.0456 (3)	1.18137 (18)	0.57482 (17)	0.0701 (6)
H11	0.0022	1.2170	0.6231	0.084*
C12	0.1934 (3)	1.1294 (2)	0.58768 (16)	0.0699 (6)
H12	0.2495	1.1285	0.6447	0.084*
C13	0.2585 (3)	1.07799 (18)	0.51452 (14)	0.0593 (5)
H13	0.3598	1.0436	0.5228	0.071*
C14	−0.2212 (4)	1.1690 (3)	0.3257 (2)	0.0902 (9)
H14A	−0.2893	1.1400	0.3777	0.135*
H14B	−0.2682	1.1528	0.2671	0.135*
H14C	−0.2159	1.2430	0.3260	0.135*
C15	−0.0676 (2)	1.58600 (13)	0.15496 (11)	0.0407 (3)
C16	−0.0377 (3)	1.48635 (14)	0.13150 (13)	0.0529 (4)
C17	0.1220 (3)	1.45853 (18)	0.10457 (17)	0.0687 (6)
H17	0.1427	1.3924	0.0872	0.082*
C18	0.2491 (3)	1.5294 (2)	0.10383 (17)	0.0691 (6)
H18	0.3555	1.5105	0.0859	0.083*
C19	0.2212 (3)	1.62651 (19)	0.12890 (15)	0.0601 (5)
H19	0.3083	1.6733	0.1291	0.072*
C20	0.0624 (2)	1.65527 (15)	0.15405 (13)	0.0485 (4)
H20	0.0429	1.7219	0.1705	0.058*
C21	−0.2474 (2)	1.53203 (16)	0.35569 (13)	0.0500 (4)
C22	−0.3193 (2)	1.45265 (15)	0.42864 (12)	0.0483 (4)
C23	−0.4520 (3)	1.38669 (16)	0.41651 (13)	0.0527 (4)
C24	−0.5045 (3)	1.31545 (18)	0.49100 (16)	0.0670 (6)
H24	−0.5931	1.2716	0.4825	0.080*
C25	−0.4266 (3)	1.3094 (2)	0.57675 (16)	0.0727 (7)
H25	−0.4626	1.2614	0.6260	0.087*
C26	−0.2968 (3)	1.3730 (2)	0.59061 (15)	0.0703 (7)
H26	−0.2450	1.3690	0.6492	0.084*
C27	−0.2425 (3)	1.44394 (18)	0.51671 (14)	0.0600 (5)
H27	−0.1529	1.4866	0.5261	0.072*
N1	0.1728 (2)	1.00103 (13)	0.27880 (11)	0.0495 (4)
N2	−0.3337 (2)	1.55288 (14)	0.27293 (11)	0.0526 (4)
O1	0.11150 (18)	0.93899 (12)	0.12765 (10)	0.0612 (4)
O2	0.3149 (2)	0.84221 (11)	0.22865 (11)	0.0659 (4)
O3	0.4060 (2)	0.99214 (16)	0.36392 (12)	0.0797 (5)
O4	−0.0573 (2)	1.12592 (13)	0.33491 (10)	0.0666 (4)
O5	−0.37606 (18)	1.61675 (14)	0.10764 (11)	0.0721 (5)
O6	−0.2480 (2)	1.73358 (11)	0.21074 (12)	0.0707 (4)
O7	−0.1198 (2)	1.57723 (14)	0.36765 (11)	0.0716 (4)
O8	−0.5245 (2)	1.39365 (13)	0.32949 (11)	0.0713 (5)
S1	0.24534 (6)	0.93882 (3)	0.19164 (3)	0.04506 (12)
S2	−0.26639 (6)	1.63258 (4)	0.18268 (3)	0.04893 (13)
Cl1	0.19015 (10)	1.17448 (5)	0.09374 (6)	0.0900 (2)
Cl2	−0.19141 (10)	1.39327 (5)	0.13476 (5)	0.0854 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C28	0.132 (3)	0.133 (3)	0.112 (2)	−0.091 (3)	−0.049 (2)	0.042 (2)
C1	0.0459 (9)	0.0403 (8)	0.0384 (8)	−0.0003 (7)	0.0031 (7)	−0.0087 (6)
C2	0.0644 (12)	0.0439 (9)	0.0494 (10)	−0.0006 (9)	0.0024 (9)	−0.0045 (7)
C3	0.0948 (18)	0.0555 (12)	0.0565 (12)	−0.0177 (12)	0.0091 (12)	−0.0021 (9)
C4	0.0816 (17)	0.0851 (17)	0.0549 (12)	−0.0299 (14)	0.0139 (11)	−0.0172 (11)
C5	0.0465 (11)	0.105 (2)	0.0630 (13)	−0.0006 (12)	0.0042 (10)	−0.0339 (13)
C6	0.0512 (11)	0.0604 (12)	0.0502 (10)	0.0086 (9)	−0.0004 (8)	−0.0147 (8)
C7	0.0534 (11)	0.0536 (10)	0.0443 (9)	−0.0040 (8)	0.0056 (8)	−0.0057 (7)
C8	0.0552 (11)	0.0433 (9)	0.0447 (9)	−0.0114 (8)	0.0098 (8)	−0.0071 (7)
C9	0.0661 (12)	0.0423 (9)	0.0476 (9)	−0.0038 (8)	0.0121 (9)	−0.0061 (7)
C10	0.0828 (16)	0.0524 (12)	0.0623 (12)	0.0013 (11)	0.0169 (11)	−0.0141 (9)
C11	0.0926 (18)	0.0607 (13)	0.0605 (12)	−0.0164 (13)	0.0222 (12)	−0.0239 (10)
C12	0.0870 (17)	0.0763 (15)	0.0491 (11)	−0.0278 (13)	0.0061 (11)	−0.0179 (10)
C13	0.0635 (13)	0.0647 (13)	0.0506 (10)	−0.0142 (10)	0.0051 (9)	−0.0105 (9)
C14	0.0921 (19)	0.103 (2)	0.0768 (16)	0.0482 (17)	−0.0087 (14)	−0.0173 (15)
C15	0.0437 (9)	0.0381 (8)	0.0395 (8)	−0.0020 (7)	0.0014 (6)	−0.0001 (6)
C16	0.0707 (13)	0.0398 (9)	0.0477 (9)	−0.0062 (9)	−0.0028 (9)	−0.0021 (7)
C17	0.0887 (17)	0.0498 (12)	0.0686 (13)	0.0219 (12)	−0.0008 (12)	−0.0119 (10)
C18	0.0566 (13)	0.0793 (16)	0.0706 (14)	0.0147 (12)	0.0058 (11)	−0.0057 (12)
C19	0.0480 (11)	0.0692 (14)	0.0620 (12)	−0.0037 (10)	0.0064 (9)	−0.0027 (10)
C20	0.0475 (10)	0.0454 (9)	0.0525 (10)	−0.0065 (8)	0.0059 (8)	−0.0049 (7)
C21	0.0490 (10)	0.0550 (11)	0.0457 (9)	−0.0053 (8)	0.0039 (8)	−0.0046 (8)
C22	0.0474 (10)	0.0529 (10)	0.0431 (9)	0.0055 (8)	0.0058 (7)	0.0007 (7)
C23	0.0539 (11)	0.0528 (10)	0.0489 (10)	0.0000 (9)	0.0040 (8)	0.0058 (8)
C24	0.0699 (14)	0.0591 (12)	0.0669 (13)	−0.0036 (10)	0.0124 (11)	0.0152 (10)
C25	0.0782 (16)	0.0750 (15)	0.0577 (12)	0.0167 (13)	0.0154 (11)	0.0230 (11)
C26	0.0752 (15)	0.0866 (17)	0.0457 (10)	0.0259 (13)	0.0012 (10)	0.0070 (10)
C27	0.0569 (12)	0.0752 (14)	0.0471 (10)	0.0115 (10)	−0.0006 (9)	−0.0029 (9)
N1	0.0474 (9)	0.0572 (10)	0.0453 (8)	0.0030 (8)	0.0056 (7)	−0.0122 (7)
N2	0.0454 (9)	0.0626 (10)	0.0471 (8)	−0.0139 (8)	0.0024 (7)	0.0072 (7)
O1	0.0529 (8)	0.0724 (10)	0.0619 (8)	−0.0076 (7)	0.0000 (7)	−0.0233 (7)
O2	0.0877 (11)	0.0367 (7)	0.0720 (9)	0.0038 (7)	0.0076 (8)	0.0002 (6)
O3	0.0606 (10)	0.1193 (15)	0.0633 (9)	0.0189 (10)	−0.0076 (8)	−0.0295 (9)
O4	0.0737 (10)	0.0727 (10)	0.0544 (8)	0.0239 (8)	0.0005 (7)	−0.0131 (7)
O5	0.0499 (8)	0.0969 (12)	0.0621 (9)	−0.0079 (8)	−0.0072 (7)	0.0262 (8)
O6	0.0714 (10)	0.0454 (8)	0.0932 (11)	0.0081 (7)	0.0246 (9)	−0.0007 (7)
O7	0.0663 (10)	0.0863 (11)	0.0612 (9)	−0.0286 (9)	−0.0060 (7)	−0.0011 (8)
O8	0.0776 (11)	0.0732 (10)	0.0592 (8)	−0.0338 (8)	−0.0117 (7)	0.0142 (7)
S1	0.0499 (3)	0.0389 (2)	0.0469 (2)	−0.00208 (18)	0.00520 (18)	−0.00783 (16)
S2	0.0410 (2)	0.0494 (3)	0.0531 (2)	−0.00109 (18)	0.00462 (18)	0.00939 (18)
Cl1	0.0898 (5)	0.0554 (3)	0.1200 (6)	0.0259 (3)	−0.0007 (4)	0.0116 (3)
Cl2	0.1187 (6)	0.0528 (3)	0.0861 (4)	−0.0362 (3)	0.0009 (4)	−0.0118 (3)

Geometric parameters (Å, º) top

C28—O8	1.421 (3)	C15—C20	1.381 (2)
C28—H28A	0.9600	C15—C16	1.386 (3)
C28—H28B	0.9600	C15—S2	1.7626 (18)
C28—H28C	0.9600	C16—C17	1.394 (3)
C1—C6	1.381 (3)	C16—Cl2	1.729 (2)
C1—C2	1.387 (3)	C17—C18	1.377 (4)
C1—S1	1.7692 (18)	C17—H17	0.9300
C2—C3	1.381 (3)	C18—C19	1.360 (3)
C2—Cl1	1.733 (2)	C18—H18	0.9300
C3—C4	1.350 (4)	C19—C20	1.383 (3)
C3—H3	0.9300	C19—H19	0.9300
C4—C5	1.381 (4)	C20—H20	0.9300
C4—H4	0.9300	C21—O7	1.208 (2)
C5—C6	1.403 (3)	C21—N2	1.372 (2)
C5—H5	0.9300	C21—C22	1.493 (3)
C6—H6	0.9300	C22—C27	1.394 (3)
C7—O3	1.206 (2)	C22—C23	1.394 (3)
C7—N1	1.375 (3)	C23—O8	1.366 (2)
C7—C8	1.498 (3)	C23—C24	1.391 (3)
C8—C13	1.380 (3)	C24—C25	1.370 (3)
C8—C9	1.402 (3)	C24—H24	0.9300
C9—O4	1.365 (2)	C25—C26	1.363 (4)
C9—C10	1.390 (3)	C25—H25	0.9300
C10—C11	1.369 (3)	C26—C27	1.387 (3)
C10—H10	0.9300	C26—H26	0.9300
C11—C12	1.368 (4)	C27—H27	0.9300
C11—H11	0.9300	N1—S1	1.6464 (16)
C12—C13	1.388 (3)	N1—HN1	0.84 (2)
C12—H12	0.9300	N2—S2	1.6456 (16)
C13—H13	0.9300	N2—HN2	0.83 (2)
C14—O4	1.431 (3)	O1—S1	1.4167 (15)
C14—H14A	0.9600	O2—S1	1.4193 (15)
C14—H14B	0.9600	O5—S2	1.4229 (16)
C14—H14C	0.9600	O6—S2	1.4159 (17)

O8—C28—H28A	109.5	C15—C16—Cl2	122.57 (17)
O8—C28—H28B	109.5	C17—C16—Cl2	117.90 (16)
H28A—C28—H28B	109.5	C18—C17—C16	119.7 (2)
O8—C28—H28C	109.5	C18—C17—H17	120.1
H28A—C28—H28C	109.5	C16—C17—H17	120.1
H28B—C28—H28C	109.5	C19—C18—C17	121.0 (2)
C6—C1—C2	119.26 (18)	C19—C18—H18	119.5
C6—C1—S1	118.13 (14)	C17—C18—H18	119.5
C2—C1—S1	122.58 (14)	C18—C19—C20	119.6 (2)
C3—C2—C1	120.8 (2)	C18—C19—H19	120.2
C3—C2—Cl1	117.68 (17)	C20—C19—H19	120.2
C1—C2—Cl1	121.52 (15)	C15—C20—C19	120.67 (19)
C4—C3—C2	119.7 (2)	C15—C20—H20	119.7
C4—C3—H3	120.2	C19—C20—H20	119.7
C2—C3—H3	120.2	O7—C21—N2	120.38 (18)
C3—C4—C5	121.4 (2)	O7—C21—C22	122.59 (18)
C3—C4—H4	119.3	N2—C21—C22	117.03 (17)
C5—C4—H4	119.3	C27—C22—C23	117.87 (18)
C4—C5—C6	119.1 (2)	C27—C22—C21	115.59 (18)
C4—C5—H5	120.4	C23—C22—C21	126.54 (17)
C6—C5—H5	120.4	O8—C23—C24	122.1 (2)
C1—C6—C5	119.7 (2)	O8—C23—C22	117.77 (16)
C1—C6—H6	120.1	C24—C23—C22	120.1 (2)
C5—C6—H6	120.1	C25—C24—C23	120.4 (2)
O3—C7—N1	120.28 (18)	C25—C24—H24	119.8
O3—C7—C8	122.73 (18)	C23—C24—H24	119.8
N1—C7—C8	116.99 (17)	C26—C25—C24	120.7 (2)
C13—C8—C9	118.47 (18)	C26—C25—H25	119.7
C13—C8—C7	115.62 (18)	C24—C25—H25	119.7
C9—C8—C7	125.90 (17)	C25—C26—C27	119.5 (2)
O4—C9—C10	122.6 (2)	C25—C26—H26	120.3
O4—C9—C8	117.88 (16)	C27—C26—H26	120.3
C10—C9—C8	119.5 (2)	C26—C27—C22	121.4 (2)
C11—C10—C9	120.5 (2)	C26—C27—H27	119.3
C11—C10—H10	119.8	C22—C27—H27	119.3
C9—C10—H10	119.8	C7—N1—S1	124.23 (14)
C12—C11—C10	120.8 (2)	C7—N1—HN1	119.7 (15)
C12—C11—H11	119.6	S1—N1—HN1	115.3 (15)
C10—C11—H11	119.6	C21—N2—S2	123.34 (14)
C11—C12—C13	119.1 (2)	C21—N2—HN2	120.8 (15)
C11—C12—H12	120.4	S2—N2—HN2	113.6 (15)
C13—C12—H12	120.4	C9—O4—C14	118.77 (17)
C8—C13—C12	121.5 (2)	C23—O8—C28	118.52 (18)
C8—C13—H13	119.2	O1—S1—O2	118.75 (10)
C12—C13—H13	119.2	O1—S1—N1	104.48 (9)
O4—C14—H14A	109.5	O2—S1—N1	109.88 (9)
O4—C14—H14B	109.5	O1—S1—C1	110.61 (9)
H14A—C14—H14B	109.5	O2—S1—C1	107.38 (9)
O4—C14—H14C	109.5	N1—S1—C1	104.90 (8)
H14A—C14—H14C	109.5	O6—S2—O5	119.47 (11)
H14B—C14—H14C	109.5	O6—S2—N2	109.83 (10)
C20—C15—C16	119.46 (17)	O5—S2—N2	104.50 (9)
C20—C15—S2	116.91 (14)	O6—S2—C15	108.02 (9)
C16—C15—S2	123.60 (14)	O5—S2—C15	108.78 (9)
C15—C16—C17	119.53 (19)	N2—S2—C15	105.37 (8)

C6—C1—C2—C3	−0.8 (3)	O7—C21—C22—C23	−170.5 (2)
S1—C1—C2—C3	−178.80 (16)	N2—C21—C22—C23	9.9 (3)
C6—C1—C2—Cl1	179.04 (14)	C27—C22—C23—O8	−178.48 (18)
S1—C1—C2—Cl1	1.0 (2)	C21—C22—C23—O8	0.5 (3)
C1—C2—C3—C4	1.0 (3)	C27—C22—C23—C24	0.3 (3)
Cl1—C2—C3—C4	−178.82 (18)	C21—C22—C23—C24	179.3 (2)
C2—C3—C4—C5	−0.4 (4)	O8—C23—C24—C25	178.7 (2)
C3—C4—C5—C6	−0.5 (3)	C22—C23—C24—C25	0.0 (3)
C2—C1—C6—C5	−0.1 (3)	C23—C24—C25—C26	0.1 (4)
S1—C1—C6—C5	178.03 (15)	C24—C25—C26—C27	−0.5 (4)
C4—C5—C6—C1	0.7 (3)	C25—C26—C27—C22	0.9 (3)
O3—C7—C8—C13	−11.6 (3)	C23—C22—C27—C26	−0.8 (3)
N1—C7—C8—C13	168.32 (17)	C21—C22—C27—C26	−179.84 (19)
O3—C7—C8—C9	167.3 (2)	O3—C7—N1—S1	0.8 (3)
N1—C7—C8—C9	−12.8 (3)	C8—C7—N1—S1	−179.16 (13)
C13—C8—C9—O4	−179.34 (17)	O7—C21—N2—S2	4.3 (3)
C7—C8—C9—O4	1.8 (3)	C22—C21—N2—S2	−176.06 (14)
C13—C8—C9—C10	1.6 (3)	C10—C9—O4—C14	−7.3 (3)
C7—C8—C9—C10	−177.29 (18)	C8—C9—O4—C14	173.6 (2)
O4—C9—C10—C11	179.4 (2)	C24—C23—O8—C28	0.0 (4)
C8—C9—C10—C11	−1.5 (3)	C22—C23—O8—C28	178.8 (3)
C9—C10—C11—C12	0.2 (3)	C7—N1—S1—O1	−179.03 (16)
C10—C11—C12—C13	1.1 (4)	C7—N1—S1—O2	52.54 (18)
C9—C8—C13—C12	−0.3 (3)	C7—N1—S1—C1	−62.61 (17)
C7—C8—C13—C12	178.66 (19)	C6—C1—S1—O1	−128.77 (15)
C11—C12—C13—C8	−1.0 (3)	C2—C1—S1—O1	49.27 (17)
C20—C15—C16—C17	−1.9 (3)	C6—C1—S1—O2	2.24 (17)
S2—C15—C16—C17	175.80 (15)	C2—C1—S1—O2	−179.72 (15)
C20—C15—C16—Cl2	177.69 (14)	C6—C1—S1—N1	119.12 (15)
S2—C15—C16—Cl2	−4.6 (2)	C2—C1—S1—N1	−62.85 (17)
C15—C16—C17—C18	1.6 (3)	C21—N2—S2—O6	−61.0 (2)
Cl2—C16—C17—C18	−178.03 (18)	C21—N2—S2—O5	169.72 (18)
C16—C17—C18—C19	−0.1 (4)	C21—N2—S2—C15	55.13 (19)
C17—C18—C19—C20	−1.1 (3)	C20—C15—S2—O6	−7.14 (17)
C16—C15—C20—C19	0.8 (3)	C16—C15—S2—O6	175.07 (15)
S2—C15—C20—C19	−177.10 (15)	C20—C15—S2—O5	123.94 (15)
C18—C19—C20—C15	0.7 (3)	C16—C15—S2—O5	−53.85 (17)
O7—C21—C22—C27	8.5 (3)	C20—C15—S2—N2	−124.48 (15)
N2—C21—C22—C27	−171.13 (18)	C16—C15—S2—N2	57.73 (17)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C22–C27 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O4	0.84 (2)	1.97 (2)	2.625 (2)	135 (2)
N2—HN2···O8	0.83 (2)	1.99 (2)	2.629 (3)	133 (2)
C13—H13···O3ⁱ	0.93	2.50	3.292 (3)	143
C10—H10···Cg	0.93	2.85	3.729 (3)	157

Symmetry code: (i) −x+1, −y+2, −z+1.

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the C22–C27 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N1—HN1···O4	0.84 (2)	1.97 (2)	2.625 (2)	135 (2)
N2—HN2···O8	0.83 (2)	1.99 (2)	2.629 (3)	133 (2)
C13—H13···O3ⁱ	0.93	2.50	3.292 (3)	143
C10—H10···Cg	0.93	2.85	3.729 (3)	157

Symmetry code: (i) −x+1, −y+2, −z+1.

Acknowledgements

PAS thanks the University Grants Commission (UGC), India, for financial support under its Minor Research Project scheme. JT thanks the Department of Science and Technology (DST), New Delhi, for the SCXRD facility under the PURSE Grant (SR/S9/Z-23/2008/11, 2009) at USIC, Karnatak University.

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Volume 69| Part 11| November 2013| Page o1716

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