2-(4-Methyl-phen-yl)-1-phenyl-sulfonyl-3-nitro-1,2-dihydro-quinoline.

In the title compound, C(22)H(18)N(2)O(4)S, the dihedral angle between the phenyl-sulfonyl ring and the methyl-phenyl ring is 67.78 (7)°. In the crystal, mol-ecules are linked by weak inter-molecular C-H⋯O inter-actions 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 = 406.44

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.048

wR(F 2) = 0.151

S = 1.03

5485 reflections

263 parameters

H-atom parameters constrained

Δρmax = 0.21 e Å−3

Δρmin = −0.23 e Å−3

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.

Crystal structure: contains datablock(s) global. DOI: 10.1107/S1600536811030455/is2758sup1.cif

Supplementary material file. DOI: 10.1107/S1600536811030455/is2758globalsup2.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C22H18N2O4S	F(000) = 848
Mr = 406.44	Dx = 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

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

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(Fo2) + (0.066P)2 + 0.3469P] where P = (Fo2 + 2Fc2)/3
5485 reflections	(Δ/σ)max < 0.001
263 parameters	Δρmax = 0.21 e Å−3
0 restraints	Δρmin = −0.23 e Å−3

	x	y	z	Uiso*/Ueq
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)

	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)

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)

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

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) .