Literature DB >> 21836974

N-[7-Eth-oxy-1-(prop-2-en-1-yl)-1H-indazol-4-yl]-4-methyl-benzene-sulfonamide.

Najat Abbassi, El Mostapha Rakib, Hafid Zouihri.

Abstract

In the title compound, C(19)H(21)N(3)O(3)S, the C-SO(2)-NH-C torsion angle is 103.72 (11)°. The almost planar indazole ring [r.m.s. deviation = 0.0202 (14) Å] is twisted away from the methyl-benzene ring by 76.87 (7)°. The vinyl group is disordered over two orientations with site occupancies of 0.622 (10) and 0.378 (10). The S atom has a distorted tetra-hedral geometry [maximum deviation: O-S-O = 119.18 (11)°]. An intra-molecular C-H⋯O hydrogen bond occurs. In the crystal, two mol-ecules are linked about a center of inversion by pairs of N-H⋯O hydrogen bonds, generating a dimer. C-H⋯π inter-actions are also observed.

Entities: Chemical Disease Gene Species

Year: 2011 PMID： 21836974 PMCID： PMC3151999 DOI： 10.1107/S1600536811019465

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For a related structure, see: Abbassi et al. (2011b ▶). For the biological activity of sulfonamides, see: Soledade et al. (2006 ▶); Lee & Lee (2002 ▶). For the synthesis of 7-ethoxy-N-alkylindazole derivatives, see: Abbassi et al. (2011a ▶).

Experimental

Crystal data

C19H21N3O3S M = 371.45 Triclinic, a = 8.2208 (3) Å b = 10.4985 (4) Å c = 11.9655 (5) Å α = 108.814 (2)° β = 92.346 (2)° γ = 107.500 (2)° V = 921.33 (6) Å3 Z = 2 Mo Kα radiation μ = 0.20 mm−1 T = 296 K 0.32 × 0.17 × 0.12 mm

Data collection

Bruker APEXII CCD detector diffractometer 23139 measured reflections 3629 independent reflections 3281 reflections with I > 2σ(I) R int = 0.023

Refinement

R[F 2 > 2σ(F 2)] = 0.042 wR(F 2) = 0.118 S = 1.08 3629 reflections 259 parameters 6 restraints H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.39 e Å−3 Δρmin = −0.32 e Å−3 Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (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/S1600536811019465/ng5164sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811019465/ng5164Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536811019465/ng5164Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₁₉H₂₁N₃O₃S	Z = 2
M_r = 371.45	F(000) = 392
Triclinic, P1	D_x = 1.339 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2208 (3) Å	Cell parameters from 341 reflections
b = 10.4985 (4) Å	θ = 2.5–27.9°
c = 11.9655 (5) Å	µ = 0.20 mm⁻¹
α = 108.814 (2)°	T = 296 K
β = 92.346 (2)°	Prism, colourless
γ = 107.500 (2)°	0.32 × 0.17 × 0.12 mm
V = 921.33 (6) Å³

Bruker APEXII CCD detector diffractometer	3281 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.023
graphite	θ_max = 26.0°, θ_min = 2.2°
ω and φ scans	h = −10→9
23139 measured reflections	k = −12→12
3629 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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	w = 1/[σ²(F_o²) + (0.053P)² + 0.4364P] where P = (F_o² + 2F_c²)/3
3629 reflections	(Δ/σ)_max < 0.001
259 parameters	Δρ_max = 0.39 e Å⁻³
6 restraints	Δρ_min = −0.32 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	U_iso*/U_eq	Occ. (<1)
C1	−0.1369 (3)	0.4744 (3)	0.2566 (2)	0.0518 (6)
C10	0.4698 (3)	0.9705 (2)	0.33160 (18)	0.0362 (4)
C11	0.5617 (2)	0.8894 (2)	0.36197 (17)	0.0345 (4)
C12	0.4804 (3)	0.7709 (2)	0.39361 (17)	0.0346 (4)
C13	0.6165 (3)	0.7239 (3)	0.4207 (2)	0.0444 (5)
C14	0.8737 (3)	1.0072 (3)	0.3443 (2)	0.0574 (7)
C15	0.4773 (4)	1.1700 (3)	0.2738 (3)	0.0595 (7)
C16	0.4069 (5)	1.1104 (4)	0.1447 (3)	0.0873 (10)
C17A	0.8898 (7)	0.9302 (9)	0.2134 (5)	0.0553 (16)	0.622 (10)
C17B	0.9147 (12)	1.0054 (12)	0.2270 (8)	0.057 (3)	0.378 (10)
C18A	0.8938 (10)	0.9902 (9)	0.1303 (6)	0.101 (3)	0.622 (10)
C18B	0.8493 (13)	0.8767 (12)	0.1399 (10)	0.079 (4)	0.378 (10)
C19	−0.3856 (5)	0.3527 (4)	−0.0543 (3)	0.0891 (11)
C2	−0.2614 (4)	0.4503 (3)	0.1640 (2)	0.0587 (7)
C3	−0.2476 (4)	0.3819 (3)	0.0462 (2)	0.0596 (7)
C4	−0.1046 (4)	0.3413 (3)	0.0237 (2)	0.0697 (8)
C5	0.0215 (4)	0.3650 (3)	0.1146 (2)	0.0595 (7)
C6	0.0038 (3)	0.4302 (2)	0.2315 (2)	0.0422 (5)
C7	0.3012 (3)	0.7306 (2)	0.39635 (17)	0.0348 (4)
C8	0.2116 (3)	0.8081 (2)	0.36507 (19)	0.0395 (5)
C9	0.2950 (3)	0.9261 (2)	0.3323 (2)	0.0408 (5)
H1	−0.1478	0.5201	0.3352	0.062*
H13	0.6020	0.6459	0.4448	0.053*
H14A	0.9800	1.0318	0.3969	0.069*
H14B	0.8479	1.0937	0.3523	0.069*
H15A	0.5564	1.2664	0.2933	0.071*
H15B	0.3835	1.1747	0.3199	0.071*
H16A	0.4981	1.0999	0.0987	0.131*
H16B	0.3571	1.1738	0.1251	0.131*
H16C	0.3198	1.0189	0.1266	0.131*
H17A	0.8970	0.8388	0.1918	0.066*	0.622 (10)
H17B	0.9807	1.0864	0.2132	0.069*	0.378 (10)
H18A	0.8868	1.0814	0.1503	0.121*	0.622 (10)
H18B	0.9036	0.9407	0.0523	0.121*	0.622 (10)
H18C	0.7840	0.7984	0.1577	0.095*	0.378 (10)
H18D	0.8694	0.8659	0.0620	0.095*	0.378 (10)
H19A	−0.3360	0.3474	−0.1263	0.134*
H19B	−0.4341	0.4283	−0.0346	0.134*
H19C	−0.4746	0.2638	−0.0662	0.134*
H2	−0.3559	0.4805	0.1810	0.070*
H3	0.146 (3)	0.630 (3)	0.484 (2)	0.049*
H4	−0.0927	0.2968	−0.0549	0.084*
H5	0.1176	0.3372	0.0973	0.071*
H8	0.0931	0.7822	0.3655	0.047*
H9	0.2298	0.9753	0.3105	0.049*
N1	0.7663 (2)	0.8046 (2)	0.40729 (19)	0.0497 (5)
N2	0.7338 (2)	0.9065 (2)	0.37229 (17)	0.0424 (4)
N3	0.2190 (2)	0.61730 (19)	0.43869 (17)	0.0405 (4)
O1	0.5640 (2)	1.08767 (18)	0.30610 (17)	0.0553 (4)
O2	0.3035 (2)	0.42371 (19)	0.29865 (18)	0.0590 (5)
O3	0.0727 (2)	0.37090 (18)	0.41924 (17)	0.0571 (5)
S1	0.15828 (7)	0.45175 (6)	0.34923 (5)	0.04300 (19)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0504 (13)	0.0580 (14)	0.0400 (12)	0.0181 (11)	0.0053 (10)	0.0081 (10)
C10	0.0355 (10)	0.0370 (10)	0.0364 (10)	0.0126 (8)	0.0059 (8)	0.0128 (8)
C11	0.0286 (9)	0.0394 (10)	0.0318 (9)	0.0119 (8)	0.0019 (7)	0.0076 (8)
C12	0.0331 (10)	0.0369 (10)	0.0316 (9)	0.0140 (8)	0.0005 (8)	0.0076 (8)
C13	0.0416 (12)	0.0485 (12)	0.0483 (12)	0.0224 (10)	0.0022 (9)	0.0177 (10)
C14	0.0285 (11)	0.0816 (18)	0.0628 (15)	0.0110 (11)	0.0078 (10)	0.0330 (14)
C15	0.0690 (17)	0.0516 (14)	0.0642 (16)	0.0189 (13)	0.0112 (13)	0.0293 (13)
C16	0.105 (3)	0.093 (3)	0.071 (2)	0.032 (2)	0.0053 (19)	0.0394 (19)
C17A	0.038 (2)	0.072 (4)	0.064 (4)	0.016 (3)	0.014 (2)	0.037 (4)
C17B	0.059 (5)	0.059 (5)	0.073 (6)	0.024 (5)	0.023 (4)	0.043 (5)
C18A	0.117 (6)	0.114 (6)	0.070 (4)	0.022 (4)	0.018 (3)	0.044 (4)
C18B	0.074 (6)	0.114 (9)	0.049 (5)	0.037 (6)	0.013 (5)	0.021 (6)
C19	0.099 (3)	0.098 (3)	0.0555 (17)	0.038 (2)	−0.0175 (17)	0.0068 (17)
C2	0.0527 (14)	0.0640 (16)	0.0520 (14)	0.0207 (12)	0.0015 (11)	0.0103 (12)
C3	0.0698 (17)	0.0534 (14)	0.0446 (13)	0.0157 (13)	−0.0038 (12)	0.0089 (11)
C4	0.088 (2)	0.0736 (19)	0.0408 (13)	0.0338 (17)	0.0084 (13)	0.0049 (13)
C5	0.0667 (17)	0.0604 (16)	0.0495 (14)	0.0285 (13)	0.0133 (12)	0.0093 (12)
C6	0.0446 (12)	0.0341 (10)	0.0426 (11)	0.0087 (9)	0.0063 (9)	0.0107 (9)
C7	0.0329 (10)	0.0345 (10)	0.0337 (10)	0.0099 (8)	0.0028 (8)	0.0090 (8)
C8	0.0285 (10)	0.0442 (11)	0.0453 (11)	0.0129 (8)	0.0052 (8)	0.0146 (9)
C9	0.0354 (11)	0.0448 (11)	0.0488 (12)	0.0200 (9)	0.0048 (9)	0.0190 (10)
N1	0.0374 (10)	0.0607 (12)	0.0561 (12)	0.0245 (9)	0.0037 (8)	0.0201 (10)
N2	0.0287 (9)	0.0521 (11)	0.0468 (10)	0.0156 (8)	0.0046 (7)	0.0160 (8)
N3	0.0408 (10)	0.0393 (10)	0.0401 (10)	0.0109 (8)	0.0068 (8)	0.0144 (8)
O1	0.0415 (9)	0.0510 (10)	0.0749 (12)	0.0130 (7)	0.0121 (8)	0.0259 (9)
O2	0.0538 (10)	0.0526 (10)	0.0732 (12)	0.0269 (8)	0.0122 (9)	0.0164 (9)
O3	0.0664 (11)	0.0446 (9)	0.0658 (11)	0.0143 (8)	0.0097 (9)	0.0303 (8)
S1	0.0451 (3)	0.0360 (3)	0.0494 (3)	0.0139 (2)	0.0067 (2)	0.0166 (2)

C1—H1	0.9300	C18B—C17B	1.345 (12)
C1—C2	1.382 (4)	C19—H19C	0.9600
C10—O1	1.376 (3)	C19—H19B	0.9600
C10—C9	1.372 (3)	C19—H19A	0.9600
C11—C10	1.412 (3)	C2—H2	0.9300
C11—C12	1.401 (3)	C2—C3	1.388 (4)
C11—N2	1.366 (3)	C3—C19	1.506 (4)
C12—C13	1.417 (3)	C3—C4	1.374 (4)
C13—H13	0.9300	C4—H4	0.9300
C13—N1	1.317 (3)	C5—H5	0.9300
C14—H14B	0.9700	C5—C4	1.378 (4)
C14—H14A	0.9700	C6—C1	1.381 (3)
C14—C17A	1.546 (7)	C6—C5	1.380 (3)
C14—C17B	1.453 (8)	C7—N3	1.436 (3)
C15—H15B	0.9700	C7—C12	1.410 (3)
C15—H15A	0.9700	C7—C8	1.370 (3)
C15—C16	1.483 (4)	C8—H8	0.9300
C16—H16C	0.9600	C8—C9	1.408 (3)
C16—H16B	0.9600	C9—H9	0.9300
C16—H16A	0.9600	N2—C14	1.443 (3)
C17A—H17A	0.9300	N2—N1	1.358 (3)
C17A—C18A	1.335 (8)	N3—H3	0.84 (3)
C17B—H17B	0.9300	O1—C15	1.403 (3)
C18A—H18B	0.9300	S1—C6	1.767 (2)
C18A—H18A	0.9300	S1—N3	1.6280 (19)
C18B—H18D	0.9300	S1—O3	1.4369 (17)
C18B—H18C	0.9300	S1—O2	1.4260 (18)

C2—C1—H1	120.3	C17A—C18A—H18B	120.0
C6—C1—H1	120.3	C17A—C18A—H18A	120.0
C6—C1—C2	119.5 (2)	H18C—C18B—H18D	120.0
O1—C10—C11	117.06 (18)	C17B—C18B—H18D	120.0
C9—C10—C11	116.67 (19)	C17B—C18B—H18C	120.0
C9—C10—O1	126.26 (19)	C3—C2—H2	119.5
C12—C11—C10	122.13 (18)	C1—C2—H2	119.5
N2—C11—C10	131.2 (2)	C1—C2—C3	121.1 (3)
N2—C11—C12	106.64 (18)	C2—C3—C19	120.9 (3)
C7—C12—C13	136.1 (2)	C4—C3—C19	120.9 (3)
C11—C12—C13	104.30 (18)	C4—C3—C2	118.2 (3)
C11—C12—C7	119.59 (18)	C5—C4—H4	119.1
C12—C13—H13	124.3	C3—C4—H4	119.1
N1—C13—H13	124.3	C3—C4—C5	121.7 (3)
N1—C13—C12	111.4 (2)	C6—C5—H5	120.3
H14A—C14—H14B	108.8	C4—C5—H5	120.3
C17A—C14—H14B	110.7	C4—C5—C6	119.4 (3)
C17B—C14—H14B	86.7	C1—C6—S1	120.01 (17)
N2—C14—H14B	110.7	C5—C6—S1	119.80 (19)
C17A—C14—H14A	110.7	C5—C6—C1	120.2 (2)
C17B—C14—H14A	108.8	C12—C7—N3	120.09 (18)
N2—C14—H14A	110.7	C8—C7—N3	121.55 (18)
C17B—C14—C17A	27.3 (3)	C8—C7—C12	118.23 (19)
N2—C14—C17A	105.1 (3)	C9—C8—H8	119.3
N2—C14—C17B	127.8 (5)	C7—C8—H8	119.3
H15A—C15—H15B	107.9	C7—C8—C9	121.47 (19)
C16—C15—H15B	109.2	C8—C9—H9	119.1
O1—C15—H15B	109.2	C10—C9—H9	119.1
C16—C15—H15A	109.2	C10—C9—C8	121.89 (19)
O1—C15—H15A	109.2	C13—N1—N2	106.45 (17)
O1—C15—C16	112.1 (3)	C11—N2—C14	129.6 (2)
H16B—C16—H16C	109.5	N1—N2—C14	119.12 (19)
H16A—C16—H16C	109.5	N1—N2—C11	111.18 (18)
C15—C16—H16C	109.5	S1—N3—H3	110.4 (19)
H16A—C16—H16B	109.5	C7—N3—H3	116.7 (18)
C15—C16—H16B	109.5	C7—N3—S1	120.46 (15)
C15—C16—H16A	109.5	C10—O1—C15	118.87 (19)
C14—C17A—H17A	118.9	N3—S1—C6	107.93 (10)
C18A—C17A—H17A	118.9	O3—S1—C6	108.09 (11)
C18A—C17A—C14	122.3 (7)	O2—S1—C6	107.73 (11)
C14—C17B—H17B	122.8	O3—S1—N3	104.80 (10)
C18B—C17B—H17B	122.8	O2—S1—N3	108.66 (11)
C18B—C17B—C14	114.3 (9)	O2—S1—O3	119.18 (11)
H18A—C18A—H18B	120.0

Cg1 is the centroid of the C7–C12 ring.

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3···O3ⁱ	0.86 (2)	2.15 (2)	3.002 (2)	171 (2)
C5—H5···O2	0.93	2.53	2.908 (3)	104
C14—H14B···O1	0.97	2.35	2.974 (2)	121
C19—H19C···Cg1ⁱⁱ	0.96	2.87	3.622 (2)	136

Table 1

Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C7–C12 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3⋯O3ⁱ	0.86 (2)	2.15 (2)	3.002 (2)	171 (2)
C14—H14B⋯O1	0.97	2.35	2.974 (2)	121
C19—H19C⋯Cg1ⁱⁱ	0.96	2.87	3.622 (2)	136

Symmetry codes: (i) ; (ii) .

4 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. Toward the control of Leptosphaeria maculans: design, syntheses, biological activity, and metabolism of potential detoxification inhibitors of the crucifer phytoalexin brassinin.

Authors: M Soledade C Pedras; Mukund Jha
Journal: Bioorg Med Chem Date: 2006-04-17 Impact factor: 3.641

3. N-(7-Eth-oxy-1H-indazol-4-yl)-4-methyl-benzene-sulfonamide.

Authors: Najat Abbassi; El Mostapha Rakib; Hafid Zouihri
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2011-05-07

4. Structure validation in chemical crystallography.

Authors: Anthony L Spek
Journal: Acta Crystallogr D Biol Crystallogr Date: 2009-01-20