2-(4-Methyl­phen­yl)-1-phenyl­sulfonyl-3-nitro-1,2-dihydro­quinoline

Kanchanadevi, J.; Anbalagan, G.; Saravanan, V.; Mohanakrishnan, A.K.; Manivannan, V.

doi:10.1107/S1600536811030455

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2225

doi:10.1107/S1600536811030455

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2-(4-Methylphenyl)-1-phenylsulfonyl-3-nitro-1,2-dihydroquinoline

J. Kanchanadevi,^a G. Anbalagan,^b V. Saravanan,^c A. K. Mohanakrishnan ^c and V. Manivannan ^d ^*

^aDepartment of Physics, Velammal Institute of Technology, Panchetty, Chennai 601 204, India, ^bDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India, ^cDepartment of Organic Chemistry, University of Madras, Guindy campus, Chennai 600 025, India, and ^dDepartment of Research and Development, PRIST University, Vallam, Thanjavur - 613 403, Tamil Nadu, India
^*Correspondence e-mail: crystallography2010@gmail.com, phdguna@gmail.com

(Received 25 July 2011; accepted 28 July 2011; online 2 August 2011)

In the title compound, C₂₂H₁₈N₂O₄S, the dihedral angle between the phenylsulfonyl ring and the methylphenyl ring is 67.78 (7)°. In the crystal, molecules are linked by weak intermolecular C—H⋯O interactions into a zigzag chain along the [101] direction.

Related literature

For the biological activity of quinoline derivatives, see: Franck et al. (2004 ); Zouhiri et al. (2005 ); Paul et al. (1969 ). For a related structure, see: Xu et al. (2011 ).

Experimental

Crystal data

C₂₂H₁₈N₂O₄S
M_r = 406.44
Monoclinic, P 2₁ /n
a = 9.7349 (5) Å
b = 17.0241 (9) Å
c = 12.1068 (6) Å
β = 90.240 (2)°
V = 2006.42 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 295 K
0.35 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.945, T_max = 0.955
26473 measured reflections
5485 independent reflections
3224 reflections with I > 2σ(I)
R_int = 0.028

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.151
S = 1.03
5485 reflections
263 parameters
H-atom parameters constrained
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4⋯O4ⁱ	0.93	2.60	3.418 (4)	148
Symmetry code: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2003 ); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; 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 datablock global. DOI: 10.1107/S1600536811030455/is2758sup1.cif

Supporting information file. DOI: 10.1107/S1600536811030455/is2758globalsup2.cml

checkCIF report

Comment top

The quinoline and its derivatives have received much scientific attention during recent years, because of their wide spectrum of pharmacological activities (Franck et al., 2004; Zouhiri et al., 2005). In addition, the nitroquinoline derivatives possess a potent mutagenic, carcinogenic and carcinostatic agent (Paul et al., 1969).

The geometric parameters of the title molecule (Fig. 1) agree well with a reported similar structure (Xu et al., 2011). The phenylsulfonly ring and the methylphenyl ring are oriented at an angle of 67.78 (7)°. The sum of bond angles around N1 [352.34 (13)°] and N2 [359.95 (2)°] indicates the sp² hybridization state of atoms N1 and N2 in the molecule. The crystal packing is controlled by a weak intermolecular C—H···O interaction.

Related literature top

For the biological activity of quinoline derivatives, see: Franck et al. (2004); Zouhiri et al. (2005); Paul et al. (1969). For a related structure, see: Xu et al. (2011).

Experimental top

To a solution of N-(2-formylphenyl) benzenesulfonamide (0.50 g, 1.91 mmol) in dry benzene (20 ml), DABACO (0.10 g, 0.95 mmol) and 1-methyl-4-(2-nitrovinyl)benzene (0.41 g, 2.29 mmol) were added. The reaction mixture was stirred at reflux condition for 24 hrs under N₂ atmosphere. The reaction mass was quenched with ice water (50 ml), extracted with chloroform (3 × 10 ml) and dried (Na₂SO₄). The solvent was removed under reduced pressure. Then the column chromatographic purification of crude product afforded pure dihydro nitroquinoline 18 as pale yellow solid with a yield of 82% and a melting point of 451 K.

Computing details top

Data collection: APEX2 (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); 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. The molecular structure of the title compound, with atom labels and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The packing of the title compound, viewed down the a axis. The C—H···O hydrogen bonds are shown as dashed lines.

2-(4-Methylphenyl)-1-phenylsulfonyl-3-nitro-1,2-dihydroquinoline top

Crystal data top

C₂₂H₁₈N₂O₄S	F(000) = 848
M_r = 406.44	D_x = 1.346 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5485 reflections
a = 9.7349 (5) Å	θ = 2.1–29.4°
b = 17.0241 (9) Å	µ = 0.19 mm⁻¹
c = 12.1068 (6) Å	T = 295 K
β = 90.240 (2)°	Block, pale yellow
V = 2006.42 (18) Å³	0.35 × 0.30 × 0.25 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	5485 independent reflections
Radiation source: fine-focus sealed tube	3224 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
Detector resolution: 0 pixels mm^-1	θ_max = 29.3°, θ_min = 2.1°
ω and ϕ scans	h = −13→7
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −23→23
T_min = 0.945, T_max = 0.955	l = −14→16
26473 measured reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.151	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.066P)² + 0.3469P] where P = (F_o² + 2F_c²)/3
5485 reflections	(Δ/σ)_max < 0.001
263 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₂H₁₈N₂O₄S	V = 2006.42 (18) Å³
M_r = 406.44	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.7349 (5) Å	µ = 0.19 mm⁻¹
b = 17.0241 (9) Å	T = 295 K
c = 12.1068 (6) Å	0.35 × 0.30 × 0.25 mm
β = 90.240 (2)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	5485 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3224 reflections with I > 2σ(I)
T_min = 0.945, T_max = 0.955	R_int = 0.028
26473 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.151	H-atom parameters constrained
S = 1.03	Δρ_max = 0.21 e Å⁻³
5485 reflections	Δρ_min = −0.23 e Å⁻³
263 parameters

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

	x	y	z	U_iso*/U_eq
C1	0.19131 (16)	0.20602 (10)	0.83358 (16)	0.0572 (4)
C2	0.1021 (2)	0.14330 (13)	0.8465 (2)	0.0782 (6)
H2	0.0747	0.1278	0.9168	0.094*
C3	0.0545 (2)	0.10423 (15)	0.7552 (3)	0.0984 (9)
H3	−0.0059	0.0624	0.7640	0.118*
C4	0.0945 (3)	0.12577 (17)	0.6509 (3)	0.1007 (9)
H4	0.0622	0.0981	0.5898	0.121*
C5	0.1819 (2)	0.18787 (15)	0.6368 (2)	0.0822 (6)
H5	0.2078	0.2028	0.5660	0.099*
C6	0.23211 (18)	0.22870 (11)	0.72767 (15)	0.0580 (4)
C7	0.32475 (19)	0.29435 (10)	0.71606 (15)	0.0583 (5)
H7	0.3352	0.3188	0.6479	0.070*
C8	0.39412 (17)	0.31926 (10)	0.80240 (15)	0.0551 (4)
C9	0.38459 (17)	0.27927 (10)	0.91304 (14)	0.0534 (4)
H9	0.4006	0.3186	0.9707	0.064*
C10	0.48831 (16)	0.21338 (10)	0.92830 (13)	0.0483 (4)
C11	0.59619 (17)	0.20168 (11)	0.85758 (14)	0.0562 (4)
H11	0.6054	0.2337	0.7958	0.067*
C12	0.69139 (18)	0.14296 (12)	0.87689 (16)	0.0639 (5)
H12	0.7646	0.1368	0.8285	0.077*
C13	0.68006 (18)	0.09341 (11)	0.96638 (15)	0.0588 (4)
C14	0.5720 (2)	0.10586 (12)	1.03651 (17)	0.0709 (5)
H14	0.5621	0.0734	1.0977	0.085*
C15	0.4780 (2)	0.16477 (12)	1.01928 (16)	0.0671 (5)
H15	0.4068	0.1720	1.0693	0.080*
C16	0.06971 (19)	0.37453 (12)	0.92595 (15)	0.0646 (5)
C17	0.1392 (2)	0.44441 (15)	0.9176 (2)	0.0860 (7)
H17	0.2226	0.4515	0.9540	0.103*
C18	0.0829 (4)	0.50453 (16)	0.8536 (3)	0.1066 (9)
H18	0.1291	0.5521	0.8465	0.128*
C19	−0.0370 (4)	0.4936 (2)	0.8029 (3)	0.1156 (11)
H19	−0.0737	0.5344	0.7610	0.139*
C20	−0.1077 (3)	0.4253 (2)	0.8102 (2)	0.1116 (10)
H20	−0.1919	0.4195	0.7746	0.134*
C21	−0.0529 (2)	0.36413 (16)	0.8715 (2)	0.0861 (7)
H21	−0.0988	0.3163	0.8757	0.103*
C22	0.7804 (2)	0.02762 (14)	0.9861 (2)	0.0873 (7)
H22A	0.8684	0.0491	1.0056	0.131*
H22B	0.7889	−0.0032	0.9201	0.131*
H22C	0.7480	−0.0050	1.0451	0.131*
N1	0.24454 (14)	0.24821 (9)	0.92602 (12)	0.0584 (4)
N2	0.48784 (19)	0.38510 (10)	0.79296 (19)	0.0773 (5)
O1	0.02787 (19)	0.24655 (12)	1.03159 (17)	0.1265 (8)
O2	0.2199 (2)	0.33166 (15)	1.09148 (12)	0.1231 (8)
O3	0.5112 (2)	0.41204 (10)	0.70211 (16)	0.1096 (6)
O4	0.5403 (2)	0.41024 (12)	0.8764 (2)	0.1219 (7)
S1	0.13716 (6)	0.29822 (4)	1.00593 (4)	0.0809 (2)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0441 (8)	0.0530 (10)	0.0747 (12)	0.0120 (7)	0.0062 (8)	0.0164 (9)
C2	0.0526 (10)	0.0659 (13)	0.1161 (18)	0.0055 (9)	0.0055 (11)	0.0266 (13)
C3	0.0614 (13)	0.0625 (14)	0.171 (3)	0.0024 (11)	−0.0212 (17)	0.0103 (18)
C4	0.0879 (17)	0.0826 (18)	0.131 (3)	0.0143 (14)	−0.0380 (17)	−0.0154 (17)
C5	0.0858 (15)	0.0804 (16)	0.0801 (15)	0.0196 (13)	−0.0177 (12)	−0.0004 (12)
C6	0.0548 (9)	0.0569 (10)	0.0622 (11)	0.0153 (8)	0.0004 (8)	0.0097 (9)
C7	0.0646 (10)	0.0564 (10)	0.0541 (10)	0.0179 (8)	0.0164 (8)	0.0176 (8)
C8	0.0548 (9)	0.0469 (9)	0.0638 (11)	0.0081 (7)	0.0159 (8)	0.0115 (8)
C9	0.0556 (9)	0.0530 (10)	0.0517 (9)	0.0065 (7)	0.0101 (7)	0.0039 (7)
C10	0.0486 (8)	0.0493 (9)	0.0469 (9)	0.0009 (7)	0.0006 (7)	0.0010 (7)
C11	0.0541 (9)	0.0612 (11)	0.0534 (10)	0.0070 (8)	0.0056 (7)	0.0073 (8)
C12	0.0552 (9)	0.0707 (12)	0.0658 (11)	0.0123 (9)	0.0033 (8)	0.0006 (10)
C13	0.0575 (10)	0.0541 (10)	0.0645 (11)	0.0066 (8)	−0.0135 (8)	−0.0024 (9)
C14	0.0784 (12)	0.0683 (13)	0.0661 (12)	0.0075 (10)	−0.0006 (10)	0.0229 (10)
C15	0.0688 (11)	0.0702 (12)	0.0623 (11)	0.0096 (9)	0.0140 (9)	0.0164 (9)
C16	0.0582 (10)	0.0726 (13)	0.0632 (11)	0.0162 (9)	0.0233 (9)	−0.0002 (9)
C17	0.0782 (13)	0.0806 (16)	0.0993 (17)	0.0089 (12)	0.0215 (12)	−0.0109 (13)
C18	0.128 (2)	0.0684 (16)	0.124 (2)	0.0191 (17)	0.041 (2)	0.0056 (16)
C19	0.134 (3)	0.112 (3)	0.100 (2)	0.055 (2)	0.030 (2)	0.0151 (19)
C20	0.0854 (17)	0.151 (3)	0.099 (2)	0.042 (2)	−0.0056 (15)	0.000 (2)
C21	0.0668 (13)	0.0997 (18)	0.0919 (16)	0.0098 (12)	0.0120 (12)	−0.0023 (14)
C22	0.0885 (15)	0.0745 (15)	0.0986 (16)	0.0267 (12)	−0.0167 (13)	0.0054 (12)
N1	0.0523 (7)	0.0649 (10)	0.0581 (9)	0.0116 (7)	0.0170 (6)	0.0135 (7)
N2	0.0770 (11)	0.0546 (10)	0.1004 (14)	0.0011 (8)	0.0181 (10)	0.0176 (10)
O1	0.1073 (12)	0.1217 (14)	0.1512 (17)	0.0298 (11)	0.0902 (12)	0.0615 (13)
O2	0.1292 (15)	0.192 (2)	0.0477 (8)	0.0691 (15)	0.0026 (9)	−0.0158 (11)
O3	0.1342 (15)	0.0769 (11)	0.1182 (14)	−0.0176 (10)	0.0390 (11)	0.0365 (10)
O4	0.1345 (16)	0.1048 (15)	0.1263 (16)	−0.0521 (13)	−0.0165 (13)	0.0139 (13)
S1	0.0799 (3)	0.1018 (5)	0.0615 (3)	0.0312 (3)	0.0356 (3)	0.0208 (3)

Geometric parameters (Å, º) top

C1—C2	1.386 (3)	C13—C14	1.371 (3)
C1—C6	1.398 (2)	C13—C22	1.505 (3)
C1—N1	1.425 (2)	C14—C15	1.373 (3)
C2—C3	1.369 (4)	C14—H14	0.9300
C2—H2	0.9300	C15—H15	0.9300
C3—C4	1.373 (4)	C16—C17	1.373 (3)
C3—H3	0.9300	C16—C21	1.373 (3)
C4—C5	1.368 (4)	C16—S1	1.747 (2)
C4—H4	0.9300	C17—C18	1.394 (4)
C5—C6	1.389 (3)	C17—H17	0.9300
C5—H5	0.9300	C18—C19	1.330 (5)
C6—C7	1.443 (3)	C18—H18	0.9300
C7—C8	1.312 (3)	C19—C20	1.355 (5)
C7—H7	0.9300	C19—H19	0.9300
C8—N2	1.450 (3)	C20—C21	1.384 (4)
C8—C9	1.506 (2)	C20—H20	0.9300
C9—N1	1.471 (2)	C21—H21	0.9300
C9—C10	1.520 (2)	C22—H22A	0.9600
C9—H9	0.9800	C22—H22B	0.9600
C10—C11	1.372 (2)	C22—H22C	0.9600
C10—C15	1.382 (2)	N1—S1	1.6620 (14)
C11—C12	1.382 (2)	N2—O4	1.208 (2)
C11—H11	0.9300	N2—O3	1.214 (2)
C12—C13	1.378 (3)	O1—S1	1.4159 (19)
C12—H12	0.9300	O2—S1	1.428 (2)

C2—C1—C6	119.8 (2)	C13—C14—C15	122.10 (18)
C2—C1—N1	121.69 (19)	C13—C14—H14	119.0
C6—C1—N1	118.49 (16)	C15—C14—H14	119.0
C3—C2—C1	119.5 (2)	C14—C15—C10	120.53 (17)
C3—C2—H2	120.2	C14—C15—H15	119.7
C1—C2—H2	120.2	C10—C15—H15	119.7
C2—C3—C4	121.1 (2)	C17—C16—C21	120.3 (2)
C2—C3—H3	119.4	C17—C16—S1	120.10 (18)
C4—C3—H3	119.4	C21—C16—S1	119.64 (18)
C5—C4—C3	120.0 (3)	C16—C17—C18	119.0 (3)
C5—C4—H4	120.0	C16—C17—H17	120.5
C3—C4—H4	120.0	C18—C17—H17	120.5
C4—C5—C6	120.3 (3)	C19—C18—C17	119.8 (3)
C4—C5—H5	119.8	C19—C18—H18	120.1
C6—C5—H5	119.8	C17—C18—H18	120.1
C5—C6—C1	119.2 (2)	C18—C19—C20	122.3 (3)
C5—C6—C7	121.89 (19)	C18—C19—H19	118.8
C1—C6—C7	118.89 (18)	C20—C19—H19	118.8
C8—C7—C6	119.48 (16)	C19—C20—C21	119.1 (3)
C8—C7—H7	120.3	C19—C20—H20	120.5
C6—C7—H7	120.3	C21—C20—H20	120.5
C7—C8—N2	120.58 (17)	C16—C21—C20	119.5 (3)
C7—C8—C9	121.95 (16)	C16—C21—H21	120.2
N2—C8—C9	117.43 (18)	C20—C21—H21	120.2
N1—C9—C8	108.54 (14)	C13—C22—H22A	109.5
N1—C9—C10	109.71 (13)	C13—C22—H22B	109.5
C8—C9—C10	113.48 (13)	H22A—C22—H22B	109.5
N1—C9—H9	108.3	C13—C22—H22C	109.5
C8—C9—H9	108.3	H22A—C22—H22C	109.5
C10—C9—H9	108.3	H22B—C22—H22C	109.5
C11—C10—C15	117.95 (16)	C1—N1—C9	115.55 (13)
C11—C10—C9	122.75 (15)	C1—N1—S1	119.18 (11)
C15—C10—C9	119.24 (15)	C9—N1—S1	117.61 (13)
C10—C11—C12	120.91 (17)	O4—N2—O3	122.9 (2)
C10—C11—H11	119.5	O4—N2—C8	118.15 (19)
C12—C11—H11	119.5	O3—N2—C8	118.9 (2)
C13—C12—C11	121.32 (17)	O1—S1—O2	120.72 (13)
C13—C12—H12	119.3	O1—S1—N1	106.53 (10)
C11—C12—H12	119.3	O2—S1—N1	105.78 (9)
C14—C13—C12	117.16 (17)	O1—S1—C16	107.62 (11)
C14—C13—C22	121.08 (19)	O2—S1—C16	108.37 (12)
C12—C13—C22	121.75 (19)	N1—S1—C16	107.11 (8)

C6—C1—C2—C3	−0.1 (3)	C21—C16—C17—C18	0.4 (3)
N1—C1—C2—C3	−179.51 (17)	S1—C16—C17—C18	−179.70 (17)
C1—C2—C3—C4	0.5 (3)	C16—C17—C18—C19	0.6 (4)
C2—C3—C4—C5	−0.9 (4)	C17—C18—C19—C20	−0.4 (4)
C3—C4—C5—C6	0.9 (3)	C18—C19—C20—C21	−0.8 (5)
C4—C5—C6—C1	−0.6 (3)	C17—C16—C21—C20	−1.6 (3)
C4—C5—C6—C7	179.81 (19)	S1—C16—C21—C20	178.51 (18)
C2—C1—C6—C5	0.2 (3)	C19—C20—C21—C16	1.8 (4)
N1—C1—C6—C5	179.58 (15)	C2—C1—N1—C9	147.01 (16)
C2—C1—C6—C7	179.81 (15)	C6—C1—N1—C9	−32.4 (2)
N1—C1—C6—C7	−0.8 (2)	C2—C1—N1—S1	−64.2 (2)
C5—C6—C7—C8	−164.16 (17)	C6—C1—N1—S1	116.43 (15)
C1—C6—C7—C8	16.2 (2)	C8—C9—N1—C1	46.92 (18)
C6—C7—C8—N2	−179.99 (15)	C10—C9—N1—C1	−77.58 (17)
C6—C7—C8—C9	2.5 (2)	C8—C9—N1—S1	−102.38 (15)
C7—C8—C9—N1	−33.2 (2)	C10—C9—N1—S1	133.12 (12)
N2—C8—C9—N1	149.26 (15)	C7—C8—N2—O4	173.7 (2)
C7—C8—C9—C10	89.0 (2)	C9—C8—N2—O4	−8.7 (3)
N2—C8—C9—C10	−88.50 (19)	C7—C8—N2—O3	−7.0 (3)
N1—C9—C10—C11	133.39 (17)	C9—C8—N2—O3	170.59 (17)
C8—C9—C10—C11	11.8 (2)	C1—N1—S1—O1	48.87 (16)
N1—C9—C10—C15	−49.3 (2)	C9—N1—S1—O1	−162.97 (14)
C8—C9—C10—C15	−170.91 (17)	C1—N1—S1—O2	178.48 (15)
C15—C10—C11—C12	0.1 (3)	C9—N1—S1—O2	−33.35 (16)
C9—C10—C11—C12	177.40 (17)	C1—N1—S1—C16	−66.07 (15)
C10—C11—C12—C13	1.2 (3)	C9—N1—S1—C16	82.10 (14)
C11—C12—C13—C14	−1.3 (3)	C17—C16—S1—O1	159.82 (17)
C11—C12—C13—C22	177.92 (18)	C21—C16—S1—O1	−20.30 (19)
C12—C13—C14—C15	0.2 (3)	C17—C16—S1—O2	27.73 (18)
C22—C13—C14—C15	−179.0 (2)	C21—C16—S1—O2	−152.39 (16)
C13—C14—C15—C10	1.0 (3)	C17—C16—S1—N1	−85.98 (17)
C11—C10—C15—C14	−1.1 (3)	C21—C16—S1—N1	93.90 (16)
C9—C10—C15—C14	−178.56 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O4ⁱ	0.93	2.60	3.418 (4)	148

Symmetry code: (i) x−1/2, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₂H₁₈N₂O₄S
M_r	406.44
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	295
a, b, c (Å)	9.7349 (5), 17.0241 (9), 12.1068 (6)
β (°)	90.240 (2)
V (Å³)	2006.42 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.35 × 0.30 × 0.25

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.945, 0.955
No. of measured, independent and observed [I > 2σ(I)] reflections	26473, 5485, 3224
R_int	0.028
(sin θ/λ)_max (Å⁻¹)	0.689

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.151, 1.03
No. of reflections	5485
No. of parameters	263
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.23

Computer programs: APEX2 (Bruker, 2003), SAINT (Bruker, 2003), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O4ⁱ	0.93	2.60	3.418 (4)	148

Symmetry code: (i) x−1/2, −y+1/2, z−1/2.

References

Bruker (2003). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Franck, X., Fournet, A., Prina, E., Mahieux, R., Hocquemiller, R. & Figadere, B. (2004). Bioorg. Med. Chem. Lett. 14, 3635–3638. Web of Science CrossRef PubMed CAS Google Scholar
Paul, J. S., Reynolds, R. C. & Montgomery, P. O'B. (1969). Cancer Res. 29, 558–570. CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Xu, L., Xu, B.-L., Lu, S.-J., Wang, B. & Kang, T.-G. (2011). Acta Cryst. E67, o957. CrossRef IUCr Journals Google Scholar
Zouhiri, F., Danet, M., Benard, C., Normand-Bayle, M., Mouscadet, J. F., Leh, H., Thomas, C. M., Mbemba, G., D'Angelo, J. & Desmaele, D. (2005). Tetrahedron Lett. 46, 2201–2205. Web of Science CrossRef CAS Google Scholar

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Volume 67| Part 9| September 2011| Page o2225

doi:10.1107/S1600536811030455

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