N-(2-Formyl-phen-yl)-4-meth-oxy-N-(4-meth-oxy-phenyl-sulfon-yl)benzene-sulfonamide.

In the title compound, C(21)H(19)NO(7)S(2), the dihedral angles between the formyl-phenyl ring and the two meth-oxy-phenyl rings are 33.87 (9) and 41.00 (10)°. The S atoms have a distorted tetra-hedral geometry and the N atom shows a trigonally planar [r.m.s. deviation = 0.0437 (13) Å] coordination. The crystal structure is stabilized by inter-molecular C-H⋯O hydrogen bonds.

Related literature

For related structures, see: Abbassi et al. (2011a ▶,b ▶). For the biological activity of sulfonamides, see: Soledade et al. (2006 ▶); Lee & Lee (2002 ▶); Lopez et al. (2010 ▶); Zuercher et al. (2010 ▶). For the synthesis of 7-eth­oxy-n class="Chemical">N-alkyl­indazole derivatives, see: Abbassi et al. (2011c ▶).

Experimental

Crystal data

C21H19NO7S2

M = 461.49

Monoclinic,

a = 9.0559 (3) Å

b = 25.8904 (10) Å

c = 9.3844 (3) Å

β = 103.423 (2)°

V = 2140.17 (13) Å3

Z = 4

Mo Kα radiation

μ = 0.29 mm−1

T = 296 K

0.24 × 0.22 × 0.17 mm

Data collection

Bruker APEXII CCD detector diffractometer

37297 measured reflections

7971 independent reflections

4874 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.139

S = 1.01

7971 reflections

282 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.35 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAIn class="Chemical">NT (Bruker, 2005 ▶); 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: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536811047192/bt5702sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811047192/bt5702Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811047192/bt5702Isup3.cml

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

C21H19NO7S2	F(000) = 960
Mr = 461.49	Dx = 1.432 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 312 reflections
a = 9.0559 (3) Å	θ = 1.7–25.7°
b = 25.8904 (10) Å	µ = 0.29 mm−1
c = 9.3844 (3) Å	T = 296 K
β = 103.423 (2)°	Prism, colourless
V = 2140.17 (13) Å3	0.24 × 0.22 × 0.17 mm
Z = 4

Bruker APEXII CCD detector diffractometer	4874 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.034
graphite	θmax = 32.9°, θmin = 2.3°
ω and φ scans	h = −12→13
37297 measured reflections	k = −39→39
7971 independent reflections	l = −14→14

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.139	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.0614P)2 + 0.4769P] where P = (Fo2 + 2Fc2)/3
7971 reflections	(Δ/σ)max < 0.001
282 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.35 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
C1	0.23459 (18)	0.05482 (6)	0.69043 (16)	0.0410 (3)
C10	0.98208 (19)	0.20588 (7)	0.8526 (2)	0.0511 (4)
C11	0.9883 (2)	0.17237 (8)	0.9684 (2)	0.0542 (4)
C12	0.8887 (2)	0.13105 (7)	0.95227 (19)	0.0493 (4)
C13	0.49327 (18)	0.11558 (6)	0.97998 (16)	0.0399 (3)
C14	0.4509 (2)	0.07804 (8)	1.0687 (2)	0.0598 (5)
C15	0.4479 (3)	0.09089 (11)	1.2108 (3)	0.0805 (7)
C16	0.4896 (3)	0.13955 (11)	1.2651 (2)	0.0784 (7)
C17	0.5319 (2)	0.17627 (9)	1.1779 (2)	0.0619 (5)
C18	0.53257 (19)	0.16520 (6)	1.03307 (17)	0.0429 (3)
C19	0.0364 (4)	−0.12570 (9)	0.6201 (3)	0.0954 (9)
C2	0.1276 (2)	0.04938 (7)	0.7745 (2)	0.0504 (4)
C20	1.1943 (3)	0.25456 (10)	0.9822 (3)	0.0869 (8)
C21	0.5676 (2)	0.20678 (6)	0.9385 (2)	0.0495 (4)
C3	0.0517 (2)	0.00361 (8)	0.7722 (2)	0.0571 (4)
C4	0.0820 (2)	−0.03719 (7)	0.68792 (19)	0.0510 (4)
C5	0.1864 (2)	−0.03151 (7)	0.6021 (2)	0.0534 (4)
C6	0.2627 (2)	0.01458 (7)	0.60319 (19)	0.0493 (4)
C7	0.78442 (18)	0.12355 (6)	0.82118 (18)	0.0421 (3)
C8	0.7775 (2)	0.15749 (7)	0.7051 (2)	0.0523 (4)
C9	0.8763 (2)	0.19839 (8)	0.7211 (2)	0.0571 (4)
H11	1.0589	0.1775	1.0565	0.065*
H12	0.8922	0.1084	1.0298	0.059*
H14	0.4250	0.0449	1.0331	0.072*
H15	0.4173	0.0664	1.2706	0.097*
H16	0.4890	0.1474	1.3616	0.094*
H17	0.5605	0.2089	1.2157	0.074*
H19A	0.0129	−0.1187	0.5168	0.143*
H19B	−0.0235	−0.1543	0.6393	0.143*
H19C	0.1422	−0.1340	0.6525	0.143*
H2	0.1078	0.0767	0.8317	0.060*
H20A	1.1526	0.2629	1.0645	0.130*
H20B	1.2588	0.2822	0.9652	0.130*
H20C	1.2524	0.2233	1.0022	0.130*
H21	0.5620	0.1994	0.8405	0.059*
H3	−0.0205	−0.0001	0.8276	0.069*
H5	0.2050	−0.0587	0.5439	0.064*
H6	0.3328	0.0186	0.5456	0.059*
H8	0.7065	0.1525	0.6172	0.063*
H9	0.8723	0.2212	0.6438	0.068*
N1	0.49649 (15)	0.10284 (5)	0.83139 (14)	0.0396 (3)
O1	0.25834 (15)	0.15158 (5)	0.75974 (15)	0.0561 (3)
O2	0.38046 (18)	0.12125 (6)	0.56618 (14)	0.0652 (4)
O3	0.61869 (16)	0.05349 (6)	0.66024 (17)	0.0710 (4)
O4	0.70366 (16)	0.03916 (5)	0.92655 (19)	0.0692 (4)
O5	0.00311 (19)	−0.08133 (6)	0.69663 (17)	0.0741 (4)
O6	1.07395 (16)	0.24749 (5)	0.85529 (19)	0.0709 (4)
O7	0.6029 (2)	0.24957 (6)	0.98157 (19)	0.0891 (5)
S1	0.33626 (5)	0.112283 (15)	0.69957 (4)	0.04289 (11)
S2	0.65454 (5)	0.073091 (15)	0.80534 (5)	0.04803 (12)

	U11	U22	U33	U12	U13	U23
C1	0.0403 (8)	0.0443 (8)	0.0376 (7)	0.0003 (6)	0.0078 (6)	−0.0025 (6)
C10	0.0407 (9)	0.0420 (8)	0.0727 (12)	0.0003 (7)	0.0179 (8)	−0.0061 (8)
C11	0.0462 (9)	0.0587 (10)	0.0539 (10)	0.0005 (8)	0.0040 (8)	−0.0094 (8)
C12	0.0489 (9)	0.0522 (9)	0.0473 (9)	0.0040 (7)	0.0123 (7)	0.0042 (7)
C13	0.0432 (8)	0.0401 (7)	0.0380 (7)	0.0025 (6)	0.0125 (6)	0.0025 (6)
C14	0.0700 (13)	0.0521 (10)	0.0626 (12)	−0.0008 (9)	0.0264 (10)	0.0140 (8)
C15	0.0957 (18)	0.0942 (18)	0.0599 (13)	0.0078 (14)	0.0347 (12)	0.0329 (12)
C16	0.0986 (18)	0.1002 (18)	0.0400 (10)	0.0142 (15)	0.0232 (11)	0.0050 (11)
C17	0.0735 (13)	0.0689 (12)	0.0412 (9)	0.0103 (10)	0.0093 (9)	−0.0091 (8)
C18	0.0461 (9)	0.0443 (8)	0.0377 (8)	0.0041 (6)	0.0082 (6)	−0.0023 (6)
C19	0.121 (2)	0.0553 (13)	0.0980 (19)	−0.0222 (14)	0.0004 (17)	−0.0040 (13)
C2	0.0469 (9)	0.0545 (10)	0.0524 (9)	0.0013 (7)	0.0170 (7)	−0.0080 (7)
C20	0.0526 (13)	0.0722 (15)	0.131 (2)	−0.0136 (11)	0.0115 (13)	−0.0302 (14)
C21	0.0553 (10)	0.0393 (8)	0.0530 (9)	−0.0014 (7)	0.0106 (8)	−0.0028 (7)
C3	0.0516 (10)	0.0657 (11)	0.0570 (11)	−0.0075 (8)	0.0184 (8)	0.0001 (8)
C4	0.0508 (10)	0.0497 (9)	0.0463 (9)	−0.0068 (7)	−0.0017 (7)	0.0048 (7)
C5	0.0579 (11)	0.0492 (9)	0.0503 (10)	−0.0008 (8)	0.0069 (8)	−0.0101 (7)
C6	0.0511 (9)	0.0533 (9)	0.0451 (9)	−0.0009 (7)	0.0145 (7)	−0.0077 (7)
C7	0.0396 (8)	0.0424 (8)	0.0465 (8)	0.0006 (6)	0.0145 (6)	−0.0027 (6)
C8	0.0448 (9)	0.0634 (11)	0.0466 (9)	−0.0049 (8)	0.0063 (7)	0.0064 (8)
C9	0.0496 (10)	0.0588 (11)	0.0630 (11)	−0.0042 (8)	0.0134 (8)	0.0159 (9)
N1	0.0400 (7)	0.0402 (6)	0.0407 (7)	−0.0009 (5)	0.0135 (5)	−0.0059 (5)
O1	0.0575 (7)	0.0436 (6)	0.0652 (8)	0.0136 (5)	0.0105 (6)	−0.0017 (5)
O2	0.0867 (10)	0.0678 (9)	0.0444 (7)	−0.0073 (7)	0.0221 (7)	0.0097 (6)
O3	0.0611 (8)	0.0730 (9)	0.0863 (10)	−0.0102 (7)	0.0317 (7)	−0.0431 (8)
O4	0.0605 (8)	0.0425 (7)	0.1075 (12)	0.0113 (6)	0.0258 (8)	0.0203 (7)
O5	0.0837 (11)	0.0611 (9)	0.0737 (9)	−0.0243 (8)	0.0108 (8)	0.0015 (7)
O6	0.0547 (8)	0.0496 (7)	0.1075 (12)	−0.0100 (6)	0.0172 (8)	−0.0060 (7)
O7	0.1287 (15)	0.0457 (8)	0.0824 (11)	−0.0226 (9)	0.0034 (10)	−0.0064 (7)
S1	0.0497 (2)	0.0397 (2)	0.0399 (2)	0.00237 (16)	0.01165 (16)	0.00260 (14)
S2	0.0449 (2)	0.0373 (2)	0.0661 (3)	0.00037 (16)	0.02144 (19)	−0.00810 (17)

C1—C2	1.391 (2)	C20—H20C	0.9600
C1—C6	1.385 (2)	C20—H20B	0.9600
C10—C9	1.389 (3)	C20—H20A	0.9600
C10—C11	1.381 (3)	C20—O6	1.427 (3)
C10—O6	1.358 (2)	C21—H21	0.9300
C11—H11	0.9300	C21—O7	1.197 (2)
C12—H12	0.9300	C3—H3	0.9300
C12—C11	1.385 (3)	C4—C5	1.385 (3)
C13—N1	1.4398 (19)	C4—C3	1.385 (3)
C13—C18	1.394 (2)	C4—O5	1.360 (2)
C13—C14	1.391 (2)	C5—H5	0.9300
C14—H14	0.9300	C6—H6	0.9300
C14—C15	1.380 (3)	C6—C5	1.378 (3)
C15—H15	0.9300	C7—C8	1.389 (2)
C15—C16	1.378 (4)	C7—C12	1.380 (2)
C16—H16	0.9300	C8—H8	0.9300
C17—H17	0.9300	C8—C9	1.371 (3)
C17—C16	1.366 (3)	C9—H9	0.9300
C18—C21	1.476 (2)	S1—C1	1.7412 (16)
C18—C17	1.390 (2)	S1—N1	1.6919 (14)
C19—H19C	0.9600	S1—O1	1.4272 (12)
C19—H19B	0.9600	S1—O2	1.4190 (13)
C19—H19A	0.9600	S2—C7	1.7411 (16)
C19—O5	1.424 (3)	S2—N1	1.6923 (13)
C2—H2	0.9300	S2—O4	1.4242 (15)
C2—C3	1.368 (3)	S2—O3	1.4184 (14)
C2—C1—S1	119.24 (13)	O6—C20—H20B	109.5
C6—C1—S1	120.27 (12)	O6—C20—H20A	109.5
C6—C1—C2	120.47 (16)	C18—C21—H21	118.3
C11—C10—C9	120.32 (16)	O7—C21—H21	118.3
O6—C10—C9	114.88 (17)	O7—C21—C18	123.38 (17)
O6—C10—C11	124.80 (18)	C4—C3—H3	119.8
C12—C11—H11	120.2	C2—C3—H3	119.8
C10—C11—H11	120.2	C2—C3—C4	120.30 (16)
C10—C11—C12	119.51 (17)	C3—C4—C5	120.25 (16)
C11—C12—H12	120.0	O5—C4—C5	124.27 (18)
C7—C12—H12	120.0	O5—C4—C3	115.49 (17)
C7—C12—C11	119.99 (16)	C4—C5—H5	120.1
C18—C13—N1	119.76 (13)	C6—C5—H5	120.1
C14—C13—N1	119.37 (15)	C6—C5—C4	119.77 (16)
C14—C13—C18	120.87 (16)	C1—C6—H6	120.2
C13—C14—H14	120.7	C5—C6—H6	120.2
C15—C14—H14	120.7	C5—C6—C1	119.69 (16)
C15—C14—C13	118.7 (2)	C8—C7—S2	120.07 (13)
C14—C15—H15	119.6	C12—C7—S2	119.40 (13)
C16—C15—H15	119.6	C12—C7—C8	120.44 (16)
C16—C15—C14	120.81 (19)	C7—C8—H8	120.2
C15—C16—H16	119.8	C9—C8—H8	120.2
C17—C16—H16	119.8	C9—C8—C7	119.53 (17)
C17—C16—C15	120.36 (19)	C10—C9—H9	119.9
C18—C17—H17	119.7	C8—C9—H9	119.9
C16—C17—H17	119.7	C8—C9—C10	120.20 (17)
C16—C17—C18	120.5 (2)	S1—N1—S2	124.80 (8)
C13—C18—C21	122.02 (14)	C13—N1—S2	116.88 (10)
C17—C18—C21	119.19 (16)	C13—N1—S1	117.92 (10)
C17—C18—C13	118.73 (16)	C4—O5—C19	118.16 (19)
H19B—C19—H19C	109.5	C10—O6—C20	117.59 (19)
H19A—C19—H19C	109.5	N1—S1—C1	105.45 (7)
O5—C19—H19C	109.5	O1—S1—C1	108.92 (8)
H19A—C19—H19B	109.5	O2—S1—C1	110.53 (8)
O5—C19—H19B	109.5	O1—S1—N1	103.45 (7)
O5—C19—H19A	109.5	O2—S1—N1	107.39 (8)
C1—C2—H2	120.3	O2—S1—O1	119.93 (8)
C3—C2—H2	120.3	N1—S2—C7	102.91 (7)
C3—C2—C1	119.50 (16)	O4—S2—C7	108.37 (9)
H20B—C20—H20C	109.5	O3—S2—C7	110.48 (9)
H20A—C20—H20C	109.5	O4—S2—N1	106.45 (8)
O6—C20—H20C	109.5	O3—S2—N1	106.78 (8)
H20A—C20—H20B	109.5	O3—S2—O4	120.37 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O4i	0.93	2.54	3.346 (2)	145.
C16—H16···O2ii	0.93	2.45	3.237 (3)	143.
C19—H19B···O6iii	0.96	2.59	3.455 (3)	151.

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O4i	0.93	2.54	3.346 (2)	145
C16—H16⋯O2ii	0.93	2.45	3.237 (3)	143
C19—H19B⋯O6iii	0.96	2.59	3.455 (3)	151

Symmetry codes: (i) ; (ii) ; (iii) .