N-(2-Formyl-phen-yl)-4-methyl-N-[(4-methyl-phen-yl)sulfon-yl]benzene-sulfon-amide.

In the title compound, C21H19NO5S2, the dihedral angles between the formyl-phenyl ring and the two methyl-phenyl rings are 29.3 (3) and 28.9 (3)°, respectively; the dihedral angle between the methyl-phenyl rings is 48.4 (2)°. The C-N-S-C torsion angles are -74.1 (2) and -105.4 (2)°. In the crystal, molecules are linked by pairs of C-H⋯O hydrogen bonds, forming inversion dimers.

Related literature

Several sulfonamide derivatives have been used as chemotherapeutic agents for their anti­bacterial, anti­fungal, anti­tumor and hypoglycemic effects, see: Chohan et al. (2010 ▶); El-Sayed et al. (2011 ▶); Seri et al. (2000 ▶). Some sulfonamide derivatives have been shown to possess carbonic anhydrases inhibitory properties, see: Suparan et al. (2000 ▶). Disulfonamides containing two sulfone groups connected to the nitro­gen atom are used for their anti­tumor activity and carbonic anhydrases inhibitory properties, see: Boriack-Sjodin et al. (1998 ▶). For related structures, see: Elgemeie et al. (2013 ▶); Mughal et al. (2012 ▶).

Experimental

Crystal data

C21H19NO5S2

M = 429.49

Monoclinic,

a = 15.5505 (6) Å

b = 7.8816 (3) Å

c = 16.6876 (7) Å

β = 103.942 (1)°

V = 1985.03 (14) Å3

Z = 4

Mo Kα radiation

μ = 0.30 mm−1

T = 199 K

0.22 × 0.14 × 0.05 mm

Data collection

Bruker SMART 1000 CCD area-detector diffractometer

14091 measured reflections

4943 independent reflections

3099 reflections with I > 2σ(I)

R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.049

wR(F 2) = 0.173

S = 1.12

4943 reflections

264 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.64 e Å−3

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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814010666/xu5787sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814010666/xu5787Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814010666/xu5787Isup3.cml

CCDC reference: 1002056

Additional supporting information: crystallographic information; 3D view; checkCIF report

C21H19NO5S2	F(000) = 896
Mr = 429.49	Dx = 1.437 Mg m−3
Monoclinic, P21/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 5757 reflections
a = 15.5505 (6) Å	θ = 2.5–28.3°
b = 7.8816 (3) Å	µ = 0.30 mm−1
c = 16.6876 (7) Å	T = 199 K
β = 103.942 (1)°	Block, colorless
V = 1985.03 (14) Å3	0.22 × 0.14 × 0.05 mm
Z = 4

Bruker SMART 1000 CCD area-detector diffractometer	3099 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.045
Graphite monochromator	θmax = 28.3°, θmin = 1.6°
phi and ω scans	h = −19→20
14091 measured reflections	k = −10→6
4943 independent reflections	l = −22→22

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)] = 0.049	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.173	H-atom parameters constrained
S = 1.12	w = 1/[σ2(Fo2) + (0.0595P)2 + 2.1799P] where P = (Fo2 + 2Fc2)/3
4943 reflections	(Δ/σ)max < 0.001
264 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.64 e Å−3

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.

	x	y	z	Uiso*/Ueq
N1	0.04365 (17)	0.3510 (3)	0.23535 (16)	0.0354 (6)
S1	−0.02134 (5)	0.27690 (10)	0.14551 (5)	0.0346 (2)
O1	−0.07076 (14)	0.1425 (3)	0.16970 (14)	0.0414 (6)
O2	−0.06558 (15)	0.4204 (3)	0.10297 (14)	0.0427 (6)
S2	0.07742 (5)	0.55504 (11)	0.25037 (5)	0.0365 (2)
O3	0.15148 (15)	0.5490 (3)	0.31970 (15)	0.0478 (6)
O4	0.08692 (16)	0.6204 (3)	0.17395 (15)	0.0483 (6)
C1	0.05293 (19)	0.1916 (4)	0.09291 (18)	0.0315 (6)
C2	0.0772 (2)	0.0219 (4)	0.1048 (2)	0.0404 (8)
H2	0.0502	−0.0489	0.1378	0.049*
C3	0.1409 (2)	−0.0426 (5)	0.0681 (2)	0.0440 (8)
H3	0.1583	−0.1580	0.0767	0.053*
C4	0.1797 (2)	0.0591 (5)	0.0188 (2)	0.0405 (8)
C5	0.1524 (2)	0.2261 (5)	0.00523 (19)	0.0398 (8)
H5	0.1773	0.2952	−0.0300	0.048*
C6	0.0891 (2)	0.2942 (4)	0.04216 (18)	0.0374 (7)
H6	0.0710	0.4091	0.0328	0.045*
C7	0.2519 (2)	−0.0112 (6)	−0.0184 (2)	0.0555 (10)
H7A	0.2885	−0.0908	0.0205	0.083*
H7B	0.2889	0.0820	−0.0297	0.083*
H7C	0.2250	−0.0705	−0.0700	0.083*
C8	−0.0103 (2)	0.6568 (4)	0.27908 (19)	0.0354 (7)
C9	−0.0739 (2)	0.7409 (4)	0.2199 (2)	0.0431 (8)
H9	−0.0693	0.7457	0.1642	0.052*
C10	−0.1442 (2)	0.8180 (5)	0.2433 (2)	0.0470 (9)
H10	−0.1882	0.8749	0.2028	0.056*
C11	−0.1520 (2)	0.8138 (4)	0.3245 (2)	0.0436 (8)
C12	−0.0872 (2)	0.7298 (5)	0.3823 (2)	0.0484 (9)
H12	−0.0918	0.7247	0.4380	0.058*
C13	−0.0163 (2)	0.6537 (5)	0.3610 (2)	0.0423 (8)
H13	0.0283	0.5994	0.4019	0.051*
C14	−0.2289 (3)	0.8997 (6)	0.3480 (3)	0.0650 (12)
H14A	−0.2802	0.8236	0.3364	0.098*
H14B	−0.2438	1.0043	0.3158	0.098*
H14C	−0.2128	0.9273	0.4070	0.098*
C15	0.0831 (2)	0.2258 (4)	0.29713 (19)	0.0337 (7)
C16	0.0375 (2)	0.1710 (4)	0.35489 (19)	0.0369 (7)
C17	0.0761 (2)	0.0474 (5)	0.4111 (2)	0.0442 (8)
H17	0.0463	0.0097	0.4513	0.053*
C18	0.1572 (2)	−0.0216 (5)	0.4098 (2)	0.0494 (9)
H18	0.1821	−0.1084	0.4478	0.059*
C19	0.2022 (2)	0.0359 (5)	0.3529 (2)	0.0493 (9)
H19	0.2586	−0.0100	0.3526	0.059*
C20	0.1653 (2)	0.1601 (5)	0.2965 (2)	0.0407 (8)
H20	0.1962	0.1999	0.2576	0.049*
C21	−0.0503 (2)	0.2395 (4)	0.3584 (2)	0.0414 (8)
H21	−0.0813	0.3076	0.3138	0.050*
O5	−0.08438 (19)	0.2136 (4)	0.41477 (18)	0.0640 (8)

	U11	U22	U33	U12	U13	U23
N1	0.0402 (14)	0.0320 (14)	0.0352 (14)	0.0043 (12)	0.0114 (11)	0.0042 (11)
S1	0.0333 (4)	0.0341 (4)	0.0357 (4)	0.0005 (3)	0.0072 (3)	0.0069 (3)
O1	0.0383 (12)	0.0377 (13)	0.0486 (13)	−0.0074 (10)	0.0113 (10)	0.0068 (11)
O2	0.0415 (12)	0.0433 (14)	0.0422 (13)	0.0095 (11)	0.0075 (10)	0.0120 (11)
S2	0.0344 (4)	0.0342 (4)	0.0414 (5)	−0.0026 (3)	0.0103 (3)	0.0029 (3)
O3	0.0388 (13)	0.0427 (14)	0.0571 (15)	−0.0027 (11)	0.0020 (11)	−0.0049 (12)
O4	0.0556 (15)	0.0426 (14)	0.0538 (15)	−0.0018 (12)	0.0270 (12)	0.0103 (12)
C1	0.0266 (14)	0.0334 (16)	0.0325 (15)	−0.0025 (13)	0.0034 (12)	0.0049 (13)
C2	0.0460 (19)	0.0364 (18)	0.0383 (17)	−0.0005 (15)	0.0089 (15)	0.0067 (14)
C3	0.051 (2)	0.0367 (19)	0.0428 (19)	0.0053 (16)	0.0086 (16)	−0.0017 (15)
C4	0.0357 (16)	0.051 (2)	0.0325 (16)	−0.0022 (16)	0.0042 (13)	−0.0082 (15)
C5	0.0375 (17)	0.050 (2)	0.0300 (16)	−0.0093 (16)	0.0050 (13)	−0.0003 (15)
C6	0.0398 (17)	0.0386 (18)	0.0321 (16)	−0.0044 (15)	0.0054 (13)	0.0042 (14)
C7	0.048 (2)	0.072 (3)	0.049 (2)	0.000 (2)	0.0151 (17)	−0.013 (2)
C8	0.0385 (17)	0.0307 (16)	0.0381 (17)	−0.0076 (14)	0.0113 (13)	0.0012 (13)
C9	0.0480 (19)	0.0396 (19)	0.0425 (19)	−0.0022 (16)	0.0121 (16)	0.0070 (15)
C10	0.0388 (18)	0.0388 (19)	0.062 (2)	0.0080 (16)	0.0084 (17)	0.0078 (17)
C11	0.0380 (18)	0.0352 (18)	0.061 (2)	−0.0084 (15)	0.0192 (16)	−0.0015 (16)
C12	0.052 (2)	0.050 (2)	0.048 (2)	−0.0018 (18)	0.0218 (17)	−0.0031 (17)
C13	0.0465 (19)	0.0402 (19)	0.0387 (18)	0.0026 (16)	0.0074 (15)	−0.0009 (15)
C14	0.051 (2)	0.059 (3)	0.094 (3)	0.007 (2)	0.034 (2)	0.000 (2)
C15	0.0343 (15)	0.0332 (17)	0.0322 (15)	0.0021 (13)	0.0052 (12)	0.0026 (13)
C16	0.0391 (17)	0.0383 (18)	0.0340 (16)	−0.0036 (14)	0.0105 (13)	0.0015 (14)
C17	0.053 (2)	0.046 (2)	0.0355 (17)	−0.0029 (17)	0.0144 (16)	0.0072 (15)
C18	0.053 (2)	0.045 (2)	0.046 (2)	0.0087 (18)	0.0053 (17)	0.0113 (17)
C19	0.0405 (18)	0.051 (2)	0.055 (2)	0.0133 (17)	0.0096 (16)	0.0113 (18)
C20	0.0330 (16)	0.045 (2)	0.0456 (19)	0.0006 (15)	0.0122 (14)	0.0056 (15)
C21	0.0400 (17)	0.0384 (19)	0.049 (2)	−0.0024 (15)	0.0170 (16)	0.0027 (15)
O5	0.0688 (18)	0.0678 (19)	0.0707 (18)	0.0055 (15)	0.0466 (16)	0.0109 (15)

N1—C15	1.452 (4)	C9—C10	1.387 (5)
N1—S2	1.691 (3)	C9—H9	0.9500
N1—S1	1.697 (3)	C10—C11	1.390 (5)
S1—O2	1.422 (2)	C10—H10	0.9500
S1—O1	1.423 (2)	C11—C12	1.384 (5)
S1—C1	1.745 (3)	C11—C14	1.507 (5)
S2—O4	1.416 (2)	C12—C13	1.375 (5)
S2—O3	1.423 (2)	C12—H12	0.9500
S2—C8	1.746 (3)	C13—H13	0.9500
C1—C6	1.385 (4)	C14—H14A	0.9800
C1—C2	1.391 (5)	C14—H14B	0.9800
C2—C3	1.380 (5)	C14—H14C	0.9800
C2—H2	0.9500	C15—C20	1.381 (4)
C3—C4	1.387 (5)	C15—C16	1.396 (4)
C3—H3	0.9500	C16—C17	1.385 (5)
C4—C5	1.385 (5)	C16—C21	1.483 (5)
C4—C7	1.512 (5)	C17—C18	1.378 (5)
C5—C6	1.388 (5)	C17—H17	0.9500
C5—H5	0.9500	C18—C19	1.384 (5)
C6—H6	0.9500	C18—H18	0.9500
C7—H7A	0.9800	C19—C20	1.382 (5)
C7—H7B	0.9800	C19—H19	0.9500
C7—H7C	0.9800	C20—H20	0.9500
C8—C9	1.386 (5)	C21—O5	1.203 (4)
C8—C13	1.393 (4)	C21—H21	0.9500
C15—N1—S2	118.6 (2)	C8—C9—C10	119.0 (3)
C15—N1—S1	116.9 (2)	C8—C9—H9	120.5
S2—N1—S1	123.77 (16)	C10—C9—H9	120.5
O2—S1—O1	120.28 (14)	C9—C10—C11	121.5 (3)
O2—S1—N1	106.30 (14)	C9—C10—H10	119.2
O1—S1—N1	104.66 (13)	C11—C10—H10	119.2
O2—S1—C1	110.77 (14)	C12—C11—C10	118.2 (3)
O1—S1—C1	108.91 (15)	C12—C11—C14	121.6 (4)
N1—S1—C1	104.58 (13)	C10—C11—C14	120.2 (4)
O4—S2—O3	120.32 (16)	C13—C12—C11	121.5 (3)
O4—S2—N1	107.97 (15)	C13—C12—H12	119.3
O3—S2—N1	104.50 (14)	C11—C12—H12	119.3
O4—S2—C8	109.75 (15)	C12—C13—C8	119.6 (3)
O3—S2—C8	108.96 (15)	C12—C13—H13	120.2
N1—S2—C8	104.02 (14)	C8—C13—H13	120.2
C6—C1—C2	120.8 (3)	C11—C14—H14A	109.5
C6—C1—S1	119.9 (3)	C11—C14—H14B	109.5
C2—C1—S1	119.3 (2)	H14A—C14—H14B	109.5
C3—C2—C1	119.4 (3)	C11—C14—H14C	109.5
C3—C2—H2	120.3	H14A—C14—H14C	109.5
C1—C2—H2	120.3	H14B—C14—H14C	109.5
C2—C3—C4	120.7 (3)	C20—C15—C16	120.9 (3)
C2—C3—H3	119.6	C20—C15—N1	118.9 (3)
C4—C3—H3	119.6	C16—C15—N1	120.2 (3)
C5—C4—C3	119.1 (3)	C17—C16—C15	118.4 (3)
C5—C4—C7	120.7 (3)	C17—C16—C21	118.9 (3)
C3—C4—C7	120.2 (3)	C15—C16—C21	122.7 (3)
C4—C5—C6	121.2 (3)	C18—C17—C16	121.0 (3)
C4—C5—H5	119.4	C18—C17—H17	119.5
C6—C5—H5	119.4	C16—C17—H17	119.5
C1—C6—C5	118.8 (3)	C17—C18—C19	119.9 (3)
C1—C6—H6	120.6	C17—C18—H18	120.1
C5—C6—H6	120.6	C19—C18—H18	120.1
C4—C7—H7A	109.5	C20—C19—C18	120.2 (3)
C4—C7—H7B	109.5	C20—C19—H19	119.9
H7A—C7—H7B	109.5	C18—C19—H19	119.9
C4—C7—H7C	109.5	C15—C20—C19	119.6 (3)
H7A—C7—H7C	109.5	C15—C20—H20	120.2
H7B—C7—H7C	109.5	C19—C20—H20	120.2
C9—C8—C13	120.1 (3)	O5—C21—C16	123.5 (3)
C9—C8—S2	119.7 (2)	O5—C21—H21	118.2
C13—C8—S2	120.2 (3)	C16—C21—H21	118.2
C15—N1—S1—O2	168.6 (2)	O4—S2—C8—C13	−160.5 (3)
S2—N1—S1—O2	−21.4 (2)	O3—S2—C8—C13	−26.8 (3)
C15—N1—S1—O1	40.3 (2)	N1—S2—C8—C13	84.2 (3)
S2—N1—S1—O1	−149.72 (18)	C13—C8—C9—C10	−1.5 (5)
C15—N1—S1—C1	−74.1 (2)	S2—C8—C9—C10	178.6 (3)
S2—N1—S1—C1	95.8 (2)	C8—C9—C10—C11	0.5 (5)
C15—N1—S2—O4	138.1 (2)	C9—C10—C11—C12	−0.1 (5)
S1—N1—S2—O4	−31.7 (2)	C9—C10—C11—C14	179.6 (4)
C15—N1—S2—O3	8.9 (3)	C10—C11—C12—C13	0.7 (5)
S1—N1—S2—O3	−160.91 (18)	C14—C11—C12—C13	−179.0 (4)
C15—N1—S2—C8	−105.4 (2)	C11—C12—C13—C8	−1.7 (6)
S1—N1—S2—C8	84.9 (2)	C9—C8—C13—C12	2.1 (5)
O2—S1—C1—C6	26.1 (3)	S2—C8—C13—C12	−178.0 (3)
O1—S1—C1—C6	160.6 (2)	S2—N1—C15—C20	−80.4 (3)
N1—S1—C1—C6	−88.0 (3)	S1—N1—C15—C20	90.1 (3)
O2—S1—C1—C2	−155.9 (2)	S2—N1—C15—C16	100.8 (3)
O1—S1—C1—C2	−21.5 (3)	S1—N1—C15—C16	−88.7 (3)
N1—S1—C1—C2	89.9 (3)	C20—C15—C16—C17	−0.7 (5)
C6—C1—C2—C3	2.7 (5)	N1—C15—C16—C17	178.0 (3)
S1—C1—C2—C3	−175.2 (3)	C20—C15—C16—C21	179.2 (3)
C1—C2—C3—C4	−1.0 (5)	N1—C15—C16—C21	−2.0 (5)
C2—C3—C4—C5	−1.4 (5)	C15—C16—C17—C18	−0.8 (5)
C2—C3—C4—C7	177.6 (3)	C21—C16—C17—C18	179.3 (3)
C3—C4—C5—C6	2.1 (5)	C16—C17—C18—C19	1.7 (6)
C7—C4—C5—C6	−177.0 (3)	C17—C18—C19—C20	−1.2 (6)
C2—C1—C6—C5	−2.0 (5)	C16—C15—C20—C19	1.2 (5)
S1—C1—C6—C5	175.9 (2)	N1—C15—C20—C19	−177.5 (3)
C4—C5—C6—C1	−0.4 (5)	C18—C19—C20—C15	−0.3 (6)
O4—S2—C8—C9	19.4 (3)	C17—C16—C21—O5	11.7 (5)
O3—S2—C8—C9	153.1 (3)	C15—C16—C21—O5	−168.3 (4)
N1—S2—C8—C9	−95.9 (3)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O2i	0.95	2.62	3.261 (4)	125

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O2i	0.95	2.62	3.261 (4)	125

Symmetry code: (i) .