4-Methyl-N-{2-[(E)-3-oxo-3-phenyl­prop-1-en-1-yl]phen­yl}benzene­sulfonamide

Kim, S.-G.

doi:10.1107/S1600536814015311

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 8| August 2014| Page o851

doi:10.1107/S1600536814015311

Open

access

4-Methyl-N-{2-[(E)-3-oxo-3-phenylprop-1-en-1-yl]phenyl}benzenesulfonamide

Sung-Gon Kim ^a ^*

^aDepartment of Chemistry, Kyonggi University, 154-42, Gwanggyosan-ro, Yeongtong-gu, Suwon 443-760, Republic of Korea
^*Correspondence e-mail: sgkim123@kyonggi.ac.kr

Edited by D.-J. Xu, Zhejiang University (Yuquan Campus), China (Received 12 June 2014; accepted 30 June 2014; online 5 July 2014)

In the title compound, C₂₂H₁₉NO₃S, the terminal phenyl and methylphenyl rings are twisted by 37.35 (12) and 49.08 (13)°, respectively, to the central benzene ring. In the crystal, molecules are linked by classical N—H⋯O hydrogen bonds and weak C—H⋯O hydrogen bonds into a three-dimensional supramolecular network.

Keywords: crystal structure.

CCDC reference: 1010977

Related literature

For applications of sulfonamides in the fields of chemistry, biology and pharmacology, see: Chohan et al. (2010 ); El-Sayed et al. (2011 ); Seri et al. (2000 ); Suparan et al. (2000 ). For related structures, see: Murugavel et al. (2012 ); Zhang et al. (2010 ); Mughal et al. (2012 ).

Experimental

Crystal data

C₂₂H₁₉NO₃S
M_r = 377.44
Monoclinic, P 2₁ /n
a = 8.9356 (7) Å
b = 10.8873 (8) Å
c = 19.3122 (14) Å
β = 99.472 (2)°
V = 1853.2 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.20 mm⁻¹
T = 200 K
0.19 × 0.12 × 0.06 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.964, T_max = 0.988
13392 measured reflections
4589 independent reflections
2366 reflections with I > 2σ(I)
R_int = 0.066

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.154
S = 1.01
4589 reflections
245 parameters
H-atom parameters constrained
Δρ_max = 0.46 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1ⁱ	0.88	2.24	2.839 (3)	125
C4—H4⋯O2ⁱ	0.95	2.51	3.272 (4)	137
C18—H18⋯O3ⁱⁱ	0.95	2.44	3.373 (3)	167
C22—H22B⋯O1ⁱⁱⁱ	0.98	2.58	3.466 (4)	150
Symmetry codes: (i) $[-x+{\script{5\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) x, y+1, z.

Data collection: SMART (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ); software used to prepare material for publication: SHELXTL and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 1010977

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536814015311/xu5798sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814015311/xu5798Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814015311/xu5798Isup3.cml

checkCIF report

Structural commentary top

For related structures, see: Murugavel et al. (2012); Zhang et al. (2010). Sulfonamides, which are already known as sulfa drugs, are an important class of compounds in the field of chemistry, biology and pharmacology. Several sulfonamide derivatives are used as chemotherapeutic agents for their antibacterial, antifungal, antitumor and hypoglycemic (Chohan et al., 2010; El-Sayed et al., 2011; Seri et al., 2000). In addition, some sulfonamide derivatives have been shown to inhibit on carbonic anhydrases (Suparan et al., 2000). In view of these potential applications and in continuation of our work, the structure of the title compound has been carried out and the results are presented here.

X-ray analysis confirms the molecular structure and atom connectivity as illustrated in Fig. 1. The geometry around atoms S and N are distorted tetrahedral and planar trigonal, respectively. The average S—O bond length is 1.427 (2) Å, while the S—N and S—C bond lengths are 1.638 (3) and 1.757 (3), respectively. The dihedral angle between the vinylphenyl ring (C1—C6) and the methylphenyl ring (C16—C21) is 49.08 (13)^o, and the dihedral angle between the vinylphenyl ring (C1—C6) and ketophenyl (C10—C15) ring is 37.35 (12)^o. The sulfonamide torsion angle 1s 64.0 (2)^o for C2—N1—S1—C16. The C==C double bond is in an E conformation and the vinylcarbonyl groups adopt extended conformations.

Synthesis and crystallization top

A solution of 4 M Na₂CO₃ in water (10 mL) was added to a solution of 2-aminobenzyl alcohol (5.0 mmol) and p-toluenesulfonyl chloride (5.5 mmol) in THF (10 mL). After stirring at room temperature for 24 h, the reaction mixture was poured into cold water and extracted with EtOAc. The resultant organic layer was washed with brine and dried over MgSO₄. The resulting residue was purified by silica gel chromatography to afford 2-(toluensulfonylamino)benzyl alcohol. Next, to solutionof 2-(toluensulfonylamino)benzyl alcohol (3.0 mmol) in CH₂Cl₂ (10 mL) was added excess MnO₂ (15 mmol). After stirring for at room temperature for 36 h, the reaction mixture was filtered under celite pad and purified by silica gel chromatography to afford 2-(toluensulfonylamino)benzaldehyde. To a solution of phenacyltriphenylphosphonium bromide (1.1 mmol) in toluene (5 mL) was added NaH (1.2 mmol) at 273 K. After stirring at 273 K for 1 h, to the reactin mixture, 2-(toluensulfonylamino)benzaldehyde (1.0 mmol) was added. After stirring at room temperature for 24 h, the reaction mixture was poured into water and extracted with EtOAc. The resultant organic layer was washed with brine and dried over MgSO₄. Theresulting residue was purified by silica gel chromatography to afford the title compound. Crystals suitable for X-ray analysis were obtained by recryatallization from an n-hexane/CH₂Cl₂ solution.

Refinement top

All H atoms were positioned geometrically, (C—H = 0.95–0.96 Å) and constrained to ride on their parent atoms, with U_iso(H) = xUeq(C), where x = 1.2 for all other H atoms.

Related literature top

For applications of sulfonamides in the fields of chemistry, biology and pharmacology, see: Chohan et al. (2010); El-Sayed et al. (2011); Seri et al. (2000); Suparan et al. (2000). For related structures, see: Murugavel et al. (2012); Zhang et al. (2010); Mughal et al. (2012).

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. A view of the molecular structure of the title compound, showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A partial view of the crystal packing of the title compound. Hydrogen atoms have been omitted for clarity.

4-Methyl-N-{2-[(E)-3-oxo-3-phenylprop-1-en-1-yl]phenyl}benzenesulfonamide top

Crystal data top

C₂₂H₁₉NO₃S	F(000) = 792
M_r = 377.44	D_x = 1.353 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 2689 reflections
a = 8.9356 (7) Å	θ = 2.4–26.1°
b = 10.8873 (8) Å	µ = 0.20 mm⁻¹
c = 19.3122 (14) Å	T = 200 K
β = 99.472 (2)°	Rod, colorless
V = 1853.2 (2) Å³	0.19 × 0.12 × 0.06 mm
Z = 4

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	4589 independent reflections
Radiation source: fine-focus sealed tube	2366 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.066
phi and ω scans	θ_max = 28.3°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −11→11
T_min = 0.964, T_max = 0.988	k = −14→13
13392 measured reflections	l = −25→24

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.154	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0583P)²] where P = (F_o² + 2F_c²)/3
4589 reflections	(Δ/σ)_max < 0.001
245 parameters	Δρ_max = 0.46 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

C₂₂H₁₉NO₃S	V = 1853.2 (2) Å³
M_r = 377.44	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.9356 (7) Å	µ = 0.20 mm⁻¹
b = 10.8873 (8) Å	T = 200 K
c = 19.3122 (14) Å	0.19 × 0.12 × 0.06 mm
β = 99.472 (2)°

Data collection top

Bruker SMART 1000 CCD area-detector diffractometer	4589 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	2366 reflections with I > 2σ(I)
T_min = 0.964, T_max = 0.988	R_int = 0.066
13392 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.154	H-atom parameters constrained
S = 1.01	Δρ_max = 0.46 e Å⁻³
4589 reflections	Δρ_min = −0.43 e Å⁻³
245 parameters

Special details top

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	1.1405 (3)	0.4390 (2)	0.37034 (13)	0.0321 (6)
C2	1.1969 (3)	0.5180 (3)	0.32288 (13)	0.0340 (6)
C3	1.2509 (3)	0.6334 (3)	0.34430 (14)	0.0407 (7)
H3	1.2877	0.6861	0.3117	0.049*
C4	1.2520 (3)	0.6731 (3)	0.41228 (15)	0.0459 (8)
H4	1.2912	0.7518	0.4267	0.055*
C5	1.1952 (3)	0.5965 (3)	0.45938 (15)	0.0439 (8)
H5	1.1947	0.6233	0.5062	0.053*
C6	1.1398 (3)	0.4822 (3)	0.43849 (13)	0.0372 (7)
H6	1.1001	0.4314	0.4711	0.045*
C7	1.0964 (3)	0.3133 (2)	0.35017 (13)	0.0336 (6)
H7	1.1236	0.2853	0.3073	0.040*
C8	1.0229 (3)	0.2331 (2)	0.38424 (13)	0.0335 (6)
H8	0.9856	0.2581	0.4253	0.040*
C9	0.9987 (3)	0.1067 (2)	0.35913 (14)	0.0326 (6)
O1	1.0479 (2)	0.07285 (18)	0.30617 (10)	0.0461 (5)
C10	0.9149 (3)	0.0178 (2)	0.39676 (13)	0.0300 (6)
C11	0.8184 (3)	0.0538 (3)	0.44267 (13)	0.0355 (7)
H11	0.8081	0.1386	0.4526	0.043*
C12	0.7373 (3)	−0.0321 (3)	0.47403 (14)	0.0426 (7)
H12	0.6711	−0.0066	0.5050	0.051*
C13	0.7536 (4)	−0.1553 (3)	0.45992 (14)	0.0470 (8)
H13	0.6968	−0.2146	0.4807	0.056*
C14	0.8511 (4)	−0.1927 (3)	0.41609 (15)	0.0493 (8)
H14	0.8632	−0.2778	0.4076	0.059*
C15	0.9315 (3)	−0.1073 (3)	0.38437 (14)	0.0400 (7)
H15	0.9986	−0.1337	0.3540	0.048*
N1	1.2050 (2)	0.4787 (2)	0.25294 (10)	0.0350 (6)
H1	1.2927	0.4543	0.2427	0.042*
S1	1.05508 (8)	0.47777 (7)	0.19146 (4)	0.0388 (2)
O2	1.1089 (2)	0.43544 (17)	0.13014 (9)	0.0465 (5)
O3	0.9384 (2)	0.41316 (19)	0.21857 (10)	0.0520 (6)
C16	0.9960 (3)	0.6311 (3)	0.17777 (13)	0.0359 (7)
C17	0.8957 (3)	0.6821 (3)	0.21770 (14)	0.0464 (8)
H17	0.8601	0.6346	0.2529	0.056*
C18	0.8480 (3)	0.8018 (3)	0.20592 (16)	0.0533 (9)
H18	0.7802	0.8365	0.2336	0.064*
C19	0.8975 (3)	0.8729 (3)	0.15412 (16)	0.0455 (8)
C20	0.9965 (3)	0.8202 (3)	0.11462 (15)	0.0423 (7)
H20	1.0310	0.8672	0.0789	0.051*
C21	1.0464 (3)	0.7003 (3)	0.12619 (14)	0.0360 (7)
H21	1.1150	0.6658	0.0988	0.043*
C22	0.8426 (4)	1.0035 (3)	0.14254 (18)	0.0638 (10)
H22A	0.8766	1.0368	0.1006	0.096*
H22B	0.8840	1.0535	0.1834	0.096*
H22C	0.7315	1.0051	0.1361	0.096*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0322 (15)	0.0345 (16)	0.0305 (14)	0.0012 (12)	0.0077 (12)	0.0040 (12)
C2	0.0333 (16)	0.0384 (17)	0.0312 (14)	0.0015 (13)	0.0079 (12)	0.0065 (13)
C3	0.0464 (18)	0.0390 (18)	0.0379 (16)	−0.0060 (14)	0.0108 (14)	0.0105 (14)
C4	0.054 (2)	0.0364 (18)	0.0481 (18)	−0.0060 (15)	0.0094 (15)	0.0004 (15)
C5	0.054 (2)	0.0407 (18)	0.0376 (16)	−0.0011 (15)	0.0102 (14)	−0.0026 (14)
C6	0.0447 (18)	0.0358 (16)	0.0336 (15)	−0.0023 (14)	0.0144 (13)	0.0054 (13)
C7	0.0361 (16)	0.0382 (17)	0.0275 (14)	0.0048 (13)	0.0078 (12)	0.0029 (12)
C8	0.0359 (16)	0.0367 (16)	0.0296 (14)	0.0006 (12)	0.0103 (12)	0.0025 (12)
C9	0.0310 (15)	0.0357 (16)	0.0321 (14)	0.0045 (12)	0.0081 (12)	−0.0012 (13)
O1	0.0521 (13)	0.0464 (13)	0.0453 (12)	0.0009 (10)	0.0245 (10)	−0.0084 (10)
C10	0.0316 (15)	0.0308 (15)	0.0268 (13)	−0.0004 (12)	0.0024 (11)	0.0014 (12)
C11	0.0415 (17)	0.0350 (17)	0.0310 (14)	−0.0024 (13)	0.0085 (13)	0.0031 (12)
C12	0.0448 (18)	0.050 (2)	0.0348 (15)	−0.0050 (15)	0.0106 (13)	0.0025 (15)
C13	0.061 (2)	0.044 (2)	0.0353 (16)	−0.0149 (16)	0.0037 (15)	0.0074 (15)
C14	0.069 (2)	0.0337 (18)	0.0433 (18)	−0.0035 (16)	0.0036 (16)	0.0000 (14)
C15	0.0487 (19)	0.0356 (17)	0.0356 (15)	0.0025 (14)	0.0065 (14)	−0.0013 (13)
N1	0.0308 (13)	0.0458 (14)	0.0300 (11)	0.0047 (11)	0.0092 (10)	0.0054 (11)
S1	0.0408 (4)	0.0434 (5)	0.0324 (4)	−0.0028 (3)	0.0070 (3)	0.0039 (3)
O2	0.0667 (15)	0.0398 (12)	0.0338 (10)	0.0078 (10)	0.0112 (10)	−0.0038 (9)
O3	0.0428 (13)	0.0633 (15)	0.0489 (12)	−0.0159 (11)	0.0043 (10)	0.0154 (11)
C16	0.0346 (16)	0.0450 (18)	0.0279 (14)	−0.0004 (13)	0.0047 (12)	−0.0019 (13)
C17	0.0419 (18)	0.069 (2)	0.0302 (15)	0.0050 (16)	0.0111 (13)	−0.0014 (15)
C18	0.0402 (19)	0.072 (3)	0.0471 (19)	0.0184 (17)	0.0051 (15)	−0.0167 (18)
C19	0.0378 (18)	0.050 (2)	0.0449 (18)	0.0093 (15)	−0.0058 (14)	−0.0130 (16)
C20	0.0419 (18)	0.0417 (18)	0.0423 (17)	0.0013 (14)	0.0039 (14)	0.0037 (14)
C21	0.0328 (16)	0.0405 (17)	0.0355 (15)	0.0025 (13)	0.0078 (12)	−0.0018 (13)
C22	0.062 (2)	0.056 (2)	0.068 (2)	0.0236 (18)	−0.0084 (18)	−0.0161 (19)

Geometric parameters (Å, º) top

C1—C6	1.399 (3)	C13—C14	1.373 (4)
C1—C2	1.409 (3)	C13—H13	0.9500
C1—C7	1.459 (4)	C14—C15	1.379 (4)
C2—C3	1.384 (4)	C14—H14	0.9500
C2—N1	1.430 (3)	C15—H15	0.9500
C3—C4	1.380 (4)	N1—S1	1.638 (2)
C3—H3	0.9500	N1—H1	0.8800
C4—C5	1.390 (4)	S1—O2	1.4259 (19)
C4—H4	0.9500	S1—O3	1.427 (2)
C5—C6	1.375 (4)	S1—C16	1.757 (3)
C5—H5	0.9500	C16—C21	1.382 (4)
C6—H6	0.9500	C16—C17	1.391 (4)
C7—C8	1.330 (3)	C17—C18	1.379 (4)
C7—H7	0.9500	C17—H17	0.9500
C8—C9	1.463 (4)	C18—C19	1.393 (4)
C8—H8	0.9500	C18—H18	0.9500
C9—O1	1.234 (3)	C19—C20	1.384 (4)
C9—C10	1.484 (4)	C19—C22	1.509 (4)
C10—C11	1.391 (4)	C20—C21	1.386 (4)
C10—C15	1.395 (4)	C20—H20	0.9500
C11—C12	1.383 (4)	C21—H21	0.9500
C11—H11	0.9500	C22—H22A	0.9800
C12—C13	1.381 (4)	C22—H22B	0.9800
C12—H12	0.9500	C22—H22C	0.9800

C6—C1—C2	117.7 (2)	C13—C14—C15	120.3 (3)
C6—C1—C7	121.6 (2)	C13—C14—H14	119.9
C2—C1—C7	120.6 (2)	C15—C14—H14	119.9
C3—C2—C1	120.3 (2)	C14—C15—C10	120.3 (3)
C3—C2—N1	119.0 (2)	C14—C15—H15	119.9
C1—C2—N1	120.7 (2)	C10—C15—H15	119.9
C4—C3—C2	121.1 (3)	C2—N1—S1	121.59 (18)
C4—C3—H3	119.5	C2—N1—H1	119.2
C2—C3—H3	119.5	S1—N1—H1	119.2
C3—C4—C5	119.2 (3)	O2—S1—O3	120.81 (13)
C3—C4—H4	120.4	O2—S1—N1	104.87 (12)
C5—C4—H4	120.4	O3—S1—N1	107.27 (12)
C6—C5—C4	120.2 (3)	O2—S1—C16	108.42 (12)
C6—C5—H5	119.9	O3—S1—C16	107.69 (13)
C4—C5—H5	119.9	N1—S1—C16	107.05 (12)
C5—C6—C1	121.5 (3)	C21—C16—C17	119.9 (3)
C5—C6—H6	119.2	C21—C16—S1	120.1 (2)
C1—C6—H6	119.2	C17—C16—S1	120.1 (2)
C8—C7—C1	128.1 (2)	C18—C17—C16	119.7 (3)
C8—C7—H7	115.9	C18—C17—H17	120.1
C1—C7—H7	115.9	C16—C17—H17	120.1
C7—C8—C9	120.8 (2)	C17—C18—C19	121.2 (3)
C7—C8—H8	119.6	C17—C18—H18	119.4
C9—C8—H8	119.6	C19—C18—H18	119.4
O1—C9—C8	120.1 (2)	C20—C19—C18	118.2 (3)
O1—C9—C10	119.2 (2)	C20—C19—C22	122.0 (3)
C8—C9—C10	120.6 (2)	C18—C19—C22	119.7 (3)
C11—C10—C15	118.6 (2)	C19—C20—C21	121.3 (3)
C11—C10—C9	123.0 (2)	C19—C20—H20	119.4
C15—C10—C9	118.4 (2)	C21—C20—H20	119.4
C12—C11—C10	120.9 (3)	C16—C21—C20	119.7 (3)
C12—C11—H11	119.6	C16—C21—H21	120.1
C10—C11—H11	119.6	C20—C21—H21	120.1
C13—C12—C11	119.4 (3)	C19—C22—H22A	109.5
C13—C12—H12	120.3	C19—C22—H22B	109.5
C11—C12—H12	120.3	H22A—C22—H22B	109.5
C14—C13—C12	120.5 (3)	C19—C22—H22C	109.5
C14—C13—H13	119.8	H22A—C22—H22C	109.5
C12—C13—H13	119.8	H22B—C22—H22C	109.5

C6—C1—C2—C3	0.8 (4)	C13—C14—C15—C10	0.2 (4)
C7—C1—C2—C3	−174.3 (3)	C11—C10—C15—C14	1.3 (4)
C6—C1—C2—N1	178.2 (2)	C9—C10—C15—C14	−177.4 (3)
C7—C1—C2—N1	3.1 (4)	C3—C2—N1—S1	−103.3 (3)
C1—C2—C3—C4	0.6 (4)	C1—C2—N1—S1	79.2 (3)
N1—C2—C3—C4	−176.9 (3)	C2—N1—S1—O2	179.0 (2)
C2—C3—C4—C5	−1.2 (4)	C2—N1—S1—O3	−51.4 (2)
C3—C4—C5—C6	0.5 (5)	C2—N1—S1—C16	64.0 (2)
C4—C5—C6—C1	0.8 (5)	O2—S1—C16—C21	−19.3 (3)
C2—C1—C6—C5	−1.5 (4)	O3—S1—C16—C21	−151.6 (2)
C7—C1—C6—C5	173.6 (3)	N1—S1—C16—C21	93.3 (2)
C6—C1—C7—C8	15.1 (4)	O2—S1—C16—C17	159.2 (2)
C2—C1—C7—C8	−170.0 (3)	O3—S1—C16—C17	26.9 (3)
C1—C7—C8—C9	−174.9 (2)	N1—S1—C16—C17	−88.2 (2)
C7—C8—C9—O1	0.7 (4)	C21—C16—C17—C18	−0.5 (4)
C7—C8—C9—C10	−179.2 (2)	S1—C16—C17—C18	−179.0 (2)
O1—C9—C10—C11	−160.3 (2)	C16—C17—C18—C19	0.6 (5)
C8—C9—C10—C11	19.6 (4)	C17—C18—C19—C20	−0.2 (4)
O1—C9—C10—C15	18.4 (4)	C17—C18—C19—C22	179.8 (3)
C8—C9—C10—C15	−161.7 (2)	C18—C19—C20—C21	−0.3 (4)
C15—C10—C11—C12	−1.7 (4)	C22—C19—C20—C21	179.7 (3)
C9—C10—C11—C12	177.0 (2)	C17—C16—C21—C20	0.0 (4)
C10—C11—C12—C13	0.5 (4)	S1—C16—C21—C20	178.5 (2)
C11—C12—C13—C14	1.1 (4)	C19—C20—C21—C16	0.4 (4)
C12—C13—C14—C15	−1.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.88	2.24	2.839 (3)	125
C4—H4···O2ⁱ	0.95	2.51	3.272 (4)	137
C18—H18···O3ⁱⁱ	0.95	2.44	3.373 (3)	167
C22—H22B···O1ⁱⁱⁱ	0.98	2.58	3.466 (4)	150

Symmetry codes: (i) −x+5/2, y+1/2, −z+1/2; (ii) −x+3/2, y+1/2, −z+1/2; (iii) x, y+1, z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.88	2.24	2.839 (3)	125
C4—H4···O2ⁱ	0.95	2.51	3.272 (4)	137
C18—H18···O3ⁱⁱ	0.95	2.44	3.373 (3)	167
C22—H22B···O1ⁱⁱⁱ	0.98	2.58	3.466 (4)	150

Symmetry codes: (i) −x+5/2, y+1/2, −z+1/2; (ii) −x+3/2, y+1/2, −z+1/2; (iii) x, y+1, z.

Acknowledgements

This work was supported by Kyonggi University Research Grant 2014.

References

Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Chohan, Z. H., Moulay, H., Youssoufi, M. H., Jarrahpour, A. & Hadda, T. B. (2010). Eur. J. Med. Chem. 45, 1189–1199. Web of Science CrossRef CAS PubMed Google Scholar
El-Sayed, N. S., El-Bendary, E. R., El-Ashry, S. M. & El-Kerdawy, M. M. (2011). Eur. J. Med. Chem. 46, 3714–3720. Web of Science CAS PubMed Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Mughal, S. Y., Khan, I. U., Harrison, W. T. A., Khan, M. H. & Tahir, M. N. (2012). Acta Cryst. E68, o3013. CSD CrossRef IUCr Journals Google Scholar
Murugavel, S., Manikandan, N., Kannan, D. & Bakthadoss, M. (2012). Acta Cryst. E68, o1009–o1010. CSD CrossRef CAS IUCr Journals Google Scholar
Seri, K., Sanai, K., Kurashima, K., Imamura, Y. & Akita, H. (2000). Eur. J. Pharmacol. 389, 253–256. Web of Science CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Suparan, C. T., Briganti, F., Tilli, S., Chegwidden, W. R. & Scozzafava, A. (2000). Bioorg. Med. Chem. 9, 703–714. Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, G.-Y., Chen, D.-J., Guo, X.-Y., Wang, S.-H. & Chang, J.-G. (2010). Acta Cryst. E66, o346. Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 70| Part 8| August 2014| Page o851

doi:10.1107/S1600536814015311

Open

access