N-{4-[(3-Methyl­phen­yl)sulfamo­yl]phen­yl}benzamide

Lahtinen, M.; Damodara, J.; Upadhyaya, P.; Nonappa; Kolehmainen, E.

doi:10.1107/S1600536811040384

organic compounds

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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2866

doi:10.1107/S1600536811040384

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N-{4-[(3-Methylphenyl)sulfamoyl]phenyl}benzamide

Manu Lahtinen,^a Jyothi Damodara,^b ^* Poornima Upadhyaya,^b Nonappa ^a and Erkki Kolehmainen ^a

^aUniversity of Jyväskylä, Department of Chemistry, PO Box 35, FI-40014 JY, Finland, and ^bDepartment of Chemistry, St. Joseph Engineering College, Vamanjoor, Mangalore 575 028, India
^*Correspondence e-mail: jyothikudva@gmail.com

(Received 28 September 2011; accepted 30 September 2011; online 8 October 2011)

In the title compound, C₂₀H₁₈N₂O₃S, the dihedral angle between the central benzene ring and the amide group is 24.1 (3)° and that between this ring and the aromatic ring of the tolyl group is 68.2 (16)°. In the crystal, adjacent molecules are linked by N—H⋯O hydrogen bonds into a linear chain running along [100]. Weak C—H⋯O contacts also occur. Extensive weak π–π interactions exist from both face-to-face and face-to-edge interactions occur between the aromatic rings [centroid–centroid distances = 3.612 (2) and 4.843 (2) Å].

Related literature

For related structures, see: Aziz-ur-Rehman et al. (2010a ,b ,c ); Khan et al. (2010 ); Shad et al. (2008 , 2009 ); Yasmeen et al. (2010 ); Gowda et al. (2007 ).

Experimental

Crystal data

C₂₀H₁₈N₂O₃S
M_r = 366.42
Triclinic, $[P \overline 1]$
a = 8.5344 (2) Å
b = 8.8477 (3) Å
c = 12.4383 (4) Å
α = 77.924 (2)°
β = 75.382 (2)°
γ = 86.537 (2)°
V = 888.67 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 123 K
0.32 × 0.20 × 0.16 mm

Data collection

Nonius KappaCCD diffractometer with Bruker APEXII detector
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.675, T_max = 0.746
11971 measured reflections
3122 independent reflections
2591 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.088
S = 1.04
3122 reflections
242 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.41 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N7—H7⋯O27ⁱ	0.86 (2)	1.99 (2)	2.813 (2)	160 (2)
N25—H25⋯O17ⁱⁱ	0.84 (2)	2.38 (2)	3.062 (2)	140 (2)
C4—H4⋯O18	0.95	2.40	3.047 (3)	125
Symmetry codes: (i) -x, -y+2, -z+2; (ii) x-1, y, z.

Data collection: COLLECT (Nonius, 1999 ); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997 ; Otwinowski et al. 2003 ); data reduction: DENZO-SMN; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811040384/ng5238sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811040384/ng5238Isup4.hkl

Supporting information file. DOI: 10.1107/S1600536811040384/ng5238Isup3.cml

checkCIF report

Comment top

Sulfonamides are very important class of compounds because of their antibacterial and enzyme inhibitor properties as well as their extensive use in medicine. As a contribution to a structural study of sulfonamide derivatives (Khan et al., 2010; Aziz-ur-Rehman et al., 2010a,b,c; Yasmeen et al., 2010; Gowda et al. 2007), we report here the title compound, N-{4-[(3-methylphenyl)sulfamoyl]phenyl}benzamide (I).

Compound (I) crystallizes in triclinic space group P-1 (No. 2) without any solvent molecules and having a single molecule in an asymmetric unit (Fig. 1). The sulfonyl and amide groups show characteristic geometries (tetrahedral and planar conformation, respectively) having typical bond distances and angles for these groups (see Tables). The dihedral angles between the central phenyl group [C(19)>C(24)] and amide group N(25)—C(26)—O(27) is about 24° and the tilting of terminal groups bonded to the sulfonamide is about 111°. The molecules are packed in infinite chains along tne a-axis enabling the hydrogen bond network to occur via a axis, whereas along c axis the packing is more columnar forming "box"-like shapes cornered by the sulfonyl groups (Fig. 2). The infinite hydrogen bond networks, along a axis, occur via N(7)—H(7)···O(27) and N(25)—H(25)···O(17) donor-acceptors with d(D···A) bond distances of 2.813 (2) and 3.062 (2) Å in angles of about 160° and 140°, respectively. Three weaker intramolecular hydrogen bonds exist between aromatic ring H atoms (H4, H20 H23) and O atoms O(27) and O(18) having d(D···A) distances of about 2.9–3.0 Å and having fairly unfavorable contact angles varying 105–125°. In addition extensive weak π-π interactions exist in the structure as both face-to-face and face-to-edge interactions occurs between the phenyl rings (Fig. 3).

Related literature top

For related structures, see: Aziz-ur-Rehman et al. (2010a,b,c); Khan et al. (2010); Shad et al. (2008, 2009); Yasmeen et al. (2010); Gowda et al. (2007).

Experimental top

4-Amino-N-(3-methylphenyl)benzenesulfonamide (0.5 g, 1.91 mmol) was taken in 20 ml dry EtOH and then benzoyl chloride (0.22 ml, 1.91 mmol) was added dropwise. The reaction medium was maintained at basic condition by adding pyridine to neutralize the produced HCl. The mixture was refluxed at 343 K for 2 h to complete the reaction. The progress of the reaction was monitored by TLC. A white precipitate obtained was filtered and purified in acetone to constant melting point. Few crystals suitable for a single-crystal structure determination were recrystallized from ethanol-acetone solution.

Computing details top

Data collection: COLLECT (Nonius, 1999); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997; Otwinowski et al. 2003); data reduction: DENZO-SMN (Otwinowski & Minor, 1997; Otwinowski et al. 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of title compound showing 50% propability displacement ellipsoids and the atomic numbering.
	Fig. 2. Molecular packing along a-, b- and c-axes from left to right, respectively.
	Fig. 3. Examples of extensive π-π interaction networks between neighbouring molecules.

N-{4-[(3-Methylphenyl)sulfamoyl]phenyl}benzamide top

Crystal data top

C₂₀H₁₈N₂O₃S	Z = 2
M_r = 366.42	F(000) = 384
Triclinic, P1	D_x = 1.369 Mg m⁻³
a = 8.5344 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.8477 (3) Å	Cell parameters from 4151 reflections
c = 12.4383 (4) Å	θ = 0.4–28.3°
α = 77.924 (2)°	µ = 0.21 mm⁻¹
β = 75.382 (2)°	T = 123 K
γ = 86.537 (2)°	Block, colourless
V = 888.67 (5) Å³	0.32 × 0.20 × 0.16 mm

Data collection top

Nonius KappaCCD diffractometer with Bruker APEXII detector	3122 independent reflections
Radiation source: fine-focus sealed tube	2591 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.675, T_max = 0.746	k = −10→10
11971 measured reflections	l = −14→14

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0225P)² + 0.7958P] where P = (F_o² + 2F_c²)/3
3122 reflections	(Δ/σ)_max = 0.001
242 parameters	Δρ_max = 0.22 e Å⁻³
2 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₂₀H₁₈N₂O₃S	γ = 86.537 (2)°
M_r = 366.42	V = 888.67 (5) Å³
Triclinic, P1	Z = 2
a = 8.5344 (2) Å	Mo Kα radiation
b = 8.8477 (3) Å	µ = 0.21 mm⁻¹
c = 12.4383 (4) Å	T = 123 K
α = 77.924 (2)°	0.32 × 0.20 × 0.16 mm
β = 75.382 (2)°

Data collection top

Nonius KappaCCD diffractometer with Bruker APEXII detector	3122 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2591 reflections with I > 2σ(I)
T_min = 0.675, T_max = 0.746	R_int = 0.040
11971 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	2 restraints
wR(F²) = 0.088	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.22 e Å⁻³
3122 reflections	Δρ_min = −0.41 e Å⁻³
242 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	−0.6233 (2)	0.8118 (2)	1.16798 (16)	0.0171 (4)
C29	−0.6766 (2)	0.6615 (2)	1.21654 (17)	0.0204 (4)
H29	−0.6033	0.5769	1.2093	0.024*
C30	−0.8372 (2)	0.6356 (3)	1.27566 (18)	0.0246 (5)
H30	−0.8736	0.5333	1.3098	0.030*
C31	−0.9443 (2)	0.7590 (3)	1.28473 (17)	0.0257 (5)
H31	−1.0549	0.7407	1.3229	0.031*
C32	−0.8910 (2)	0.9090 (3)	1.23850 (18)	0.0260 (5)
H32	−0.9646	0.9933	1.2458	0.031*
C33	−0.7305 (2)	0.9358 (2)	1.18166 (17)	0.0204 (4)
H33	−0.6932	1.0387	1.1519	0.025*
C26	−0.4514 (2)	0.8461 (2)	1.10486 (16)	0.0167 (4)
C22	−0.2076 (2)	0.7276 (2)	0.99572 (16)	0.0152 (4)
C23	−0.0888 (2)	0.7983 (2)	1.02747 (17)	0.0180 (4)
H23	−0.1190	0.8589	1.0843	0.022*
C24	0.0732 (2)	0.7796 (2)	0.97568 (17)	0.0176 (4)
H24	0.1545	0.8273	0.9968	0.021*
C19	0.1162 (2)	0.6904 (2)	0.89228 (16)	0.0155 (4)
C20	−0.0010 (2)	0.6204 (2)	0.86079 (17)	0.0176 (4)
H20	0.0293	0.5595	0.8042	0.021*
C21	−0.1630 (2)	0.6395 (2)	0.91227 (16)	0.0177 (4)
H21	−0.2439	0.5923	0.8904	0.021*
C5	0.3326 (2)	0.9120 (2)	0.65597 (16)	0.0192 (4)
C6	0.3642 (2)	1.0699 (2)	0.62394 (17)	0.0220 (4)
H6	0.4185	1.1168	0.6663	0.026*
C1	0.3176 (2)	1.1604 (3)	0.53119 (18)	0.0276 (5)
C1B	0.3540 (3)	1.3306 (3)	0.4984 (2)	0.0390 (6)
H1B1	0.4356	1.3519	0.4260	0.058*
H1B2	0.3955	1.3617	0.5571	0.058*
H1B3	0.2548	1.3890	0.4909	0.058*
C2	0.2371 (3)	1.0896 (3)	0.47118 (19)	0.0326 (6)
H2	0.2038	1.1492	0.4078	0.039*
C3	0.2051 (3)	0.9333 (3)	0.50290 (19)	0.0321 (5)
H3	0.1492	0.8870	0.4612	0.039*
C4	0.2530 (2)	0.8425 (3)	0.59478 (17)	0.0251 (5)
H4	0.2317	0.7347	0.6153	0.030*
N25	−0.37393 (19)	0.73597 (19)	1.04858 (14)	0.0174 (4)
N7	0.39203 (18)	0.82946 (19)	0.74938 (14)	0.0172 (4)
O27	−0.38543 (16)	0.96655 (15)	1.10373 (12)	0.0208 (3)
O17	0.41159 (15)	0.63241 (15)	0.91408 (11)	0.0196 (3)
O18	0.33106 (15)	0.55489 (15)	0.75619 (12)	0.0204 (3)
S16	0.32251 (5)	0.66440 (5)	0.82764 (4)	0.01601 (14)
H7	0.415 (2)	0.887 (2)	0.7913 (17)	0.019*
H25	−0.430 (2)	0.668 (2)	1.0390 (18)	0.019*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C28	0.0168 (10)	0.0206 (10)	0.0157 (10)	0.0016 (8)	−0.0056 (8)	−0.0060 (8)
C29	0.0170 (10)	0.0216 (10)	0.0235 (11)	0.0017 (8)	−0.0045 (8)	−0.0075 (9)
C30	0.0206 (11)	0.0283 (12)	0.0251 (12)	−0.0053 (9)	−0.0024 (9)	−0.0081 (9)
C31	0.0157 (10)	0.0428 (13)	0.0197 (11)	−0.0004 (9)	−0.0019 (8)	−0.0114 (10)
C32	0.0205 (11)	0.0363 (13)	0.0235 (12)	0.0122 (9)	−0.0070 (9)	−0.0126 (10)
C33	0.0226 (10)	0.0221 (10)	0.0172 (10)	0.0051 (8)	−0.0064 (8)	−0.0051 (8)
C26	0.0179 (10)	0.0181 (10)	0.0147 (10)	0.0022 (8)	−0.0062 (8)	−0.0023 (8)
C22	0.0150 (9)	0.0134 (9)	0.0158 (10)	−0.0007 (7)	−0.0032 (7)	0.0000 (8)
C23	0.0201 (10)	0.0163 (10)	0.0192 (10)	0.0025 (8)	−0.0060 (8)	−0.0066 (8)
C24	0.0164 (10)	0.0160 (10)	0.0218 (11)	−0.0003 (8)	−0.0069 (8)	−0.0044 (8)
C19	0.0139 (9)	0.0161 (9)	0.0146 (10)	−0.0002 (7)	−0.0017 (7)	−0.0007 (8)
C20	0.0180 (10)	0.0172 (10)	0.0185 (10)	−0.0002 (8)	−0.0038 (8)	−0.0060 (8)
C21	0.0164 (10)	0.0169 (10)	0.0215 (11)	−0.0022 (8)	−0.0067 (8)	−0.0042 (8)
C5	0.0127 (9)	0.0245 (11)	0.0169 (10)	0.0040 (8)	−0.0001 (8)	−0.0022 (8)
C6	0.0177 (10)	0.0236 (11)	0.0201 (11)	0.0026 (8)	0.0021 (8)	−0.0033 (9)
C1	0.0200 (11)	0.0306 (12)	0.0227 (12)	0.0089 (9)	0.0048 (9)	0.0012 (9)
C1B	0.0414 (14)	0.0288 (13)	0.0329 (14)	0.0107 (11)	0.0030 (11)	0.0064 (11)
C2	0.0221 (11)	0.0484 (15)	0.0206 (12)	0.0082 (10)	−0.0036 (9)	0.0031 (10)
C3	0.0228 (11)	0.0491 (15)	0.0244 (12)	−0.0033 (10)	−0.0073 (9)	−0.0048 (11)
C4	0.0209 (11)	0.0307 (12)	0.0226 (12)	−0.0027 (9)	−0.0044 (9)	−0.0034 (9)
N25	0.0131 (8)	0.0159 (8)	0.0241 (9)	−0.0008 (7)	−0.0027 (7)	−0.0083 (7)
N7	0.0161 (8)	0.0172 (9)	0.0190 (9)	−0.0018 (7)	−0.0052 (7)	−0.0038 (7)
O27	0.0210 (7)	0.0163 (7)	0.0256 (8)	−0.0022 (6)	−0.0036 (6)	−0.0073 (6)
O17	0.0158 (7)	0.0213 (7)	0.0223 (8)	0.0018 (6)	−0.0071 (6)	−0.0032 (6)
O18	0.0183 (7)	0.0191 (7)	0.0249 (8)	0.0006 (6)	−0.0026 (6)	−0.0100 (6)
S16	0.0132 (2)	0.0155 (2)	0.0188 (3)	0.00087 (18)	−0.00303 (18)	−0.00364 (19)

Geometric parameters (Å, º) top

C28—C29	1.392 (3)	C20—C21	1.386 (3)
C28—C33	1.396 (3)	C20—H20	0.9500
C28—C26	1.495 (3)	C21—H21	0.9500
C29—C30	1.390 (3)	C5—C4	1.388 (3)
C29—H29	0.9500	C5—C6	1.394 (3)
C30—C31	1.385 (3)	C5—N7	1.428 (3)
C30—H30	0.9500	C6—C1	1.391 (3)
C31—C32	1.386 (3)	C6—H6	0.9500
C31—H31	0.9500	C1—C2	1.389 (3)
C32—C33	1.383 (3)	C1—C1B	1.506 (3)
C32—H32	0.9500	C1B—H1B1	0.9800
C33—H33	0.9500	C1B—H1B2	0.9800
C26—O27	1.231 (2)	C1B—H1B3	0.9800
C26—N25	1.360 (2)	C2—C3	1.380 (3)
C22—C21	1.390 (3)	C2—H2	0.9500
C22—C23	1.400 (3)	C3—C4	1.390 (3)
C22—N25	1.410 (2)	C3—H3	0.9500
C23—C24	1.386 (3)	C4—H4	0.9500
C23—H23	0.9500	N25—H25	0.835 (15)
C24—C19	1.396 (3)	N7—S16	1.6280 (16)
C24—H24	0.9500	N7—H7	0.861 (15)
C19—C20	1.383 (3)	O17—S16	1.4400 (14)
C19—S16	1.7642 (18)	O18—S16	1.4328 (14)

C29—C28—C33	119.77 (18)	C22—C21—H21	119.8
C29—C28—C26	121.93 (17)	C4—C5—C6	119.79 (19)
C33—C28—C26	118.25 (18)	C4—C5—N7	123.68 (18)
C30—C29—C28	119.81 (18)	C6—C5—N7	116.48 (18)
C30—C29—H29	120.1	C1—C6—C5	121.3 (2)
C28—C29—H29	120.1	C1—C6—H6	119.3
C31—C30—C29	120.0 (2)	C5—C6—H6	119.3
C31—C30—H30	120.0	C2—C1—C6	118.3 (2)
C29—C30—H30	120.0	C2—C1—C1B	121.6 (2)
C30—C31—C32	120.40 (19)	C6—C1—C1B	120.1 (2)
C30—C31—H31	119.8	C1—C1B—H1B1	109.5
C32—C31—H31	119.8	C1—C1B—H1B2	109.5
C33—C32—C31	119.89 (19)	H1B1—C1B—H1B2	109.5
C33—C32—H32	120.1	C1—C1B—H1B3	109.5
C31—C32—H32	120.1	H1B1—C1B—H1B3	109.5
C32—C33—C28	120.08 (19)	H1B2—C1B—H1B3	109.5
C32—C33—H33	120.0	C3—C2—C1	120.6 (2)
C28—C33—H33	120.0	C3—C2—H2	119.7
O27—C26—N25	122.61 (17)	C1—C2—H2	119.7
O27—C26—C28	121.90 (17)	C2—C3—C4	121.2 (2)
N25—C26—C28	115.48 (16)	C2—C3—H3	119.4
C21—C22—C23	119.99 (17)	C4—C3—H3	119.4
C21—C22—N25	117.37 (16)	C5—C4—C3	118.8 (2)
C23—C22—N25	122.59 (17)	C5—C4—H4	120.6
C24—C23—C22	119.69 (18)	C3—C4—H4	120.6
C24—C23—H23	120.2	C26—N25—C22	127.54 (16)
C22—C23—H23	120.2	C26—N25—H25	118.0 (15)
C23—C24—C19	119.67 (17)	C22—N25—H25	114.2 (15)
C23—C24—H24	120.2	C5—N7—S16	124.74 (13)
C19—C24—H24	120.2	C5—N7—H7	114.5 (14)
C20—C19—C24	120.72 (17)	S16—N7—H7	109.6 (14)
C20—C19—S16	119.57 (15)	O18—S16—O17	118.60 (8)
C24—C19—S16	119.70 (14)	O18—S16—N7	109.02 (8)
C19—C20—C21	119.61 (18)	O17—S16—N7	104.61 (8)
C19—C20—H20	120.2	O18—S16—C19	107.45 (8)
C21—C20—H20	120.2	O17—S16—C19	108.77 (8)
C20—C21—C22	120.32 (17)	N7—S16—C19	107.99 (8)
C20—C21—H21	119.8

C33—C28—C29—C30	1.8 (3)	C5—C6—C1—C2	0.6 (3)
C26—C28—C29—C30	179.18 (18)	C5—C6—C1—C1B	−179.75 (18)
C28—C29—C30—C31	0.9 (3)	C6—C1—C2—C3	−0.3 (3)
C29—C30—C31—C32	−2.2 (3)	C1B—C1—C2—C3	−180.0 (2)
C30—C31—C32—C33	0.8 (3)	C1—C2—C3—C4	−0.4 (3)
C31—C32—C33—C28	1.9 (3)	C6—C5—C4—C3	−0.6 (3)
C29—C28—C33—C32	−3.2 (3)	N7—C5—C4—C3	−177.87 (18)
C26—C28—C33—C32	179.34 (18)	C2—C3—C4—C5	0.9 (3)
C29—C28—C26—O27	−148.36 (19)	O27—C26—N25—C22	9.8 (3)
C33—C28—C26—O27	29.1 (3)	C28—C26—N25—C22	−170.63 (17)
C29—C28—C26—N25	32.1 (3)	C21—C22—N25—C26	−158.59 (19)
C33—C28—C26—N25	−150.49 (18)	C23—C22—N25—C26	24.1 (3)
C21—C22—C23—C24	−0.3 (3)	C4—C5—N7—S16	−24.1 (3)
N25—C22—C23—C24	177.01 (17)	C6—C5—N7—S16	158.56 (14)
C22—C23—C24—C19	0.0 (3)	C5—N7—S16—O18	55.80 (17)
C23—C24—C19—C20	0.0 (3)	C5—N7—S16—O17	−176.39 (15)
C23—C24—C19—S16	−179.17 (14)	C5—N7—S16—C19	−60.64 (17)
C24—C19—C20—C21	0.3 (3)	C20—C19—S16—O18	−5.69 (18)
S16—C19—C20—C21	179.41 (15)	C24—C19—S16—O18	173.47 (15)
C19—C20—C21—C22	−0.5 (3)	C20—C19—S16—O17	−135.24 (15)
C23—C22—C21—C20	0.5 (3)	C24—C19—S16—O17	43.92 (18)
N25—C22—C21—C20	−176.90 (17)	C20—C19—S16—N7	111.78 (16)
C4—C5—C6—C1	−0.1 (3)	C24—C19—S16—N7	−69.07 (17)
N7—C5—C6—C1	177.35 (17)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7···O27ⁱ	0.86 (2)	1.99 (2)	2.813 (2)	160 (2)
N25—H25···O17ⁱⁱ	0.84 (2)	2.38 (2)	3.062 (2)	140 (2)
C4—H4···O18	0.95	2.40	3.047 (3)	125
C20—H20···O18	0.95	2.49	2.884 (2)	105
C23—H23···O27	0.95	2.39	2.907 (2)	114

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

Experimental details

Crystal data
Chemical formula	C₂₀H₁₈N₂O₃S
M_r	366.42
Crystal system, space group	Triclinic, P1
Temperature (K)	123
a, b, c (Å)	8.5344 (2), 8.8477 (3), 12.4383 (4)
α, β, γ (°)	77.924 (2), 75.382 (2), 86.537 (2)
V (Å³)	888.67 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.32 × 0.20 × 0.16

Data collection
Diffractometer	Nonius KappaCCD diffractometer with Bruker APEXII detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.675, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	11971, 3122, 2591
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.088, 1.04
No. of reflections	3122
No. of parameters	242
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.41

Computer programs: COLLECT (Nonius, 1999), DENZO-SMN (Otwinowski & Minor, 1997; Otwinowski et al. 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7···O27ⁱ	0.863 (19)	1.987 (19)	2.813 (2)	159.9 (17)
N25—H25···O17ⁱⁱ	0.836 (18)	2.379 (19)	3.062 (2)	139.5 (17)
C4—H4···O18	0.95	2.40	3.047 (3)	125

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

References

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Volume 67| Part 11| November 2011| Page o2866

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