Literature DB >> 25309293

Crystal structure of N-(3-chloro-1-methyl-1H-indazol-5-yl)-4-meth-oxy-benzene-sulfonamide.

Hakima Chicha¹, El Mostapha Rakib¹, Ahmed Gamouh¹, Mohamed Saadi², Lahcen El Ammari².

Abstract

In the title compound, C15H14ClN3O3S, the dihedral angle between the planes of the indazole ring system (r.m.s. deviation = 0.007 Å) and the benzene ring is 89.05 (7)°. The meth-oxy C atom deviates from its attached ring by 0.196 (3) Å. In the crystal, inversion dimers linked by pairs of N-H⋯O hydrogen bonds generate R 2 (2)(8) loops. The dimers are connected into [010] chains by C-H⋯O inter-actions.

Entities: CellLine Chemical Disease Gene

Keywords: benzenesulfonamides; crystal structure; hydrogen bonding

Year: 2014 PMID： 25309293 PMCID： PMC4186104 DOI： 10.1107/S1600536814017747

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

Related literature

For the biological activity of sulfonamides, see: El-Sayed et al. (2011 ▶); Mustafa et al. (2012 ▶); Scozzafava et al. (2003 ▶). For similar compounds, see: Abbassi et al. (2012 ▶, 2013 ▶); Chicha et al. (2014 ▶).

Experimental

Crystal data

C15H14ClN3O3S M = 351.80 Triclinic, a = 8.2023 (1) Å b = 10.6312 (2) Å c = 10.8957 (2) Å α = 117.523 (1)° β = 93.095 (1)° γ = 103.166 (1)° V = 806.36 (2) Å3 Z = 2 Mo Kα radiation μ = 0.38 mm−1 T = 296 K 0.40 × 0.36 × 0.31 mm

Data collection

Bruker X8 APEX CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.693, T max = 0.747 20115 measured reflections 4526 independent reflections 3707 reflections with I > 2σ(I) R int = 0.028

Refinement

R[F 2 > 2σ(F 2)] = 0.038 wR(F 2) = 0.116 S = 1.03 4526 reflections 209 parameters H-atom parameters constrained Δρmax = 0.32 e Å−3 Δρmin = −0.37 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶). Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814017747/hb7261sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814017747/hb7261Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S1600536814017747/hb7261Isup3.cml Click here for additional data file. . DOI: 10.1107/S1600536814017747/hb7261fig1.tif Molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. Click here for additional data file. N . DOI: 10.1107/S1600536814017747/hb7261fig2.tif Crystal structure of the title compound, showing molecules linked by N3–H3N⋯O2 hydrogen bond and forming dimers linked by C5–H5⋯O3 interaction. CCDC reference: 1017531 Additional supporting information: crystallographic information; 3D view; checkCIF report

C₁₅H₁₄ClN₃O₃S	Z = 2
M_r = 351.80	F(000) = 364
Triclinic, P1	D_x = 1.449 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.2023 (1) Å	Cell parameters from 4526 reflections
b = 10.6312 (2) Å	θ = 2.6–29.6°
c = 10.8957 (2) Å	µ = 0.38 mm⁻¹
α = 117.523 (1)°	T = 296 K
β = 93.095 (1)°	Block, colourless
γ = 103.166 (1)°	0.40 × 0.36 × 0.31 mm
V = 806.36 (2) Å³

Bruker X8 APEX CCD diffractometer	4526 independent reflections
Radiation source: fine-focus sealed tube	3707 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.028
φ and ω scans	θ_max = 29.6°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −11→11
T_min = 0.693, T_max = 0.747	k = −14→14
20115 measured reflections	l = −15→15

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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.062P)² + 0.1878P] where P = (F_o² + 2F_c²)/3
4526 reflections	(Δ/σ)_max = 0.001
209 parameters	Δρ_max = 0.32 e Å⁻³
0 restraints	Δρ_min = −0.37 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
C1	0.5360 (3)	0.1820 (2)	−0.2354 (2)	0.0641 (5)
H1A	0.5166	0.1185	−0.3355	0.096*
H1B	0.4305	0.1986	−0.2072	0.096*
H1C	0.5801	0.1361	−0.1885	0.096*
C2	0.8383 (2)	0.47591 (16)	−0.23208 (15)	0.0391 (3)
C3	0.84060 (18)	0.54753 (16)	−0.08554 (14)	0.0352 (3)
C4	0.72093 (19)	0.44264 (17)	−0.06796 (16)	0.0397 (3)
C5	0.6874 (2)	0.4716 (2)	0.06598 (18)	0.0493 (4)
H5	0.6097	0.4017	0.0787	0.059*
C6	0.7734 (2)	0.60633 (19)	0.17665 (17)	0.0476 (4)
H6	0.7515	0.6289	0.2662	0.057*
C7	0.8951 (2)	0.71369 (17)	0.16058 (14)	0.0385 (3)
C8	0.93096 (19)	0.68456 (16)	0.02938 (14)	0.0375 (3)
H8	1.0120	0.7532	0.0177	0.045*
C9	0.88896 (18)	1.06974 (16)	0.26748 (13)	0.0364 (3)
C10	0.83288 (19)	1.04012 (17)	0.13088 (14)	0.0407 (3)
H10	0.8815	0.9839	0.0568	0.049*
C11	0.7053 (2)	1.09469 (18)	0.10689 (15)	0.0441 (3)
H11	0.6677	1.0754	0.0162	0.053*
C12	0.6321 (2)	1.17864 (17)	0.21742 (16)	0.0413 (3)
C13	0.6836 (2)	1.20357 (17)	0.35215 (16)	0.0435 (3)
H13	0.6319	1.2566	0.4254	0.052*
C14	0.8118 (2)	1.14935 (17)	0.37674 (14)	0.0413 (3)
H14	0.8469	1.1661	0.4670	0.050*
C15	0.4427 (3)	1.3276 (3)	0.2942 (3)	0.0797 (7)
H15A	0.3597	1.3573	0.2564	0.120*
H15B	0.5324	1.4136	0.3600	0.120*
H15C	0.3895	1.2767	0.3414	0.120*
N1	0.65760 (18)	0.32210 (15)	−0.19782 (15)	0.0478 (3)
N2	0.72912 (18)	0.34244 (15)	−0.29918 (14)	0.0456 (3)
N3	0.98123 (19)	0.84656 (15)	0.28741 (13)	0.0459 (3)
H3N	0.9455	0.8563	0.3661	0.057 (5)*
O1	1.16088 (15)	0.99481 (14)	0.19715 (12)	0.0520 (3)
O2	1.13503 (15)	1.10282 (14)	0.44851 (11)	0.0535 (3)
O3	0.51174 (17)	1.23162 (16)	0.18293 (14)	0.0575 (3)
S1	1.05777 (5)	1.00891 (4)	0.30176 (3)	0.04069 (12)
Cl1	0.95605 (6)	0.54559 (5)	−0.32303 (4)	0.05614 (14)

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0617 (11)	0.0421 (9)	0.0786 (13)	0.0032 (8)	0.0160 (10)	0.0262 (9)
C2	0.0482 (8)	0.0355 (7)	0.0327 (6)	0.0140 (6)	0.0112 (6)	0.0147 (6)
C3	0.0424 (7)	0.0354 (7)	0.0325 (6)	0.0176 (6)	0.0115 (5)	0.0170 (5)
C4	0.0443 (7)	0.0386 (8)	0.0420 (7)	0.0166 (6)	0.0133 (6)	0.0215 (6)
C5	0.0585 (10)	0.0506 (9)	0.0507 (9)	0.0187 (8)	0.0230 (7)	0.0315 (8)
C6	0.0631 (10)	0.0545 (10)	0.0396 (7)	0.0273 (8)	0.0224 (7)	0.0285 (7)
C7	0.0492 (8)	0.0416 (8)	0.0314 (6)	0.0243 (6)	0.0126 (6)	0.0174 (6)
C8	0.0468 (7)	0.0363 (7)	0.0308 (6)	0.0157 (6)	0.0108 (5)	0.0154 (5)
C9	0.0443 (7)	0.0328 (7)	0.0264 (6)	0.0081 (5)	0.0090 (5)	0.0110 (5)
C10	0.0462 (8)	0.0430 (8)	0.0263 (6)	0.0092 (6)	0.0109 (5)	0.0128 (6)
C11	0.0498 (8)	0.0489 (9)	0.0311 (6)	0.0088 (7)	0.0072 (6)	0.0197 (6)
C12	0.0446 (8)	0.0372 (7)	0.0413 (7)	0.0073 (6)	0.0085 (6)	0.0203 (6)
C13	0.0540 (9)	0.0394 (8)	0.0344 (7)	0.0165 (7)	0.0153 (6)	0.0137 (6)
C14	0.0535 (8)	0.0406 (8)	0.0256 (6)	0.0146 (6)	0.0103 (6)	0.0120 (5)
C15	0.0883 (16)	0.0877 (17)	0.0909 (17)	0.0560 (14)	0.0333 (14)	0.0502 (14)
N1	0.0523 (8)	0.0374 (7)	0.0485 (7)	0.0079 (6)	0.0134 (6)	0.0187 (6)
N2	0.0536 (8)	0.0367 (7)	0.0393 (6)	0.0111 (6)	0.0103 (6)	0.0134 (5)
N3	0.0649 (8)	0.0476 (8)	0.0272 (5)	0.0231 (6)	0.0116 (5)	0.0165 (5)
O1	0.0485 (6)	0.0604 (8)	0.0370 (5)	0.0149 (5)	0.0163 (5)	0.0151 (5)
O2	0.0533 (7)	0.0610 (8)	0.0281 (5)	0.0122 (6)	0.0018 (4)	0.0097 (5)
O3	0.0610 (7)	0.0654 (8)	0.0594 (7)	0.0281 (6)	0.0141 (6)	0.0362 (7)
S1	0.0437 (2)	0.0454 (2)	0.02480 (16)	0.01330 (15)	0.00761 (13)	0.01019 (14)
Cl1	0.0743 (3)	0.0487 (2)	0.0361 (2)	0.0060 (2)	0.01902 (18)	0.01758 (17)

C1—N1	1.448 (2)	C9—S1	1.7465 (16)
C1—H1A	0.9600	C10—C11	1.374 (2)
C1—H1B	0.9600	C10—H10	0.9300
C1—H1C	0.9600	C11—C12	1.392 (2)
C2—N2	1.320 (2)	C11—H11	0.9300
C2—C3	1.4129 (18)	C12—O3	1.357 (2)
C2—Cl1	1.7085 (15)	C12—C13	1.388 (2)
C3—C8	1.401 (2)	C13—C14	1.378 (2)
C3—C4	1.401 (2)	C13—H13	0.9300
C4—N1	1.362 (2)	C14—H14	0.9300
C4—C5	1.403 (2)	C15—O3	1.423 (3)
C5—C6	1.362 (2)	C15—H15A	0.9600
C5—H5	0.9300	C15—H15B	0.9600
C6—C7	1.419 (2)	C15—H15C	0.9600
C6—H6	0.9300	N1—N2	1.3577 (19)
C7—C8	1.3796 (19)	N3—S1	1.6260 (15)
C7—N3	1.4283 (19)	N3—H3N	0.8897
C8—H8	0.9300	O1—S1	1.4286 (11)
C9—C14	1.3884 (19)	O2—S1	1.4429 (11)
C9—C10	1.3974 (18)

N1—C1—H1A	109.5	C10—C11—C12	120.42 (13)
N1—C1—H1B	109.5	C10—C11—H11	119.8
H1A—C1—H1B	109.5	C12—C11—H11	119.8
N1—C1—H1C	109.5	O3—C12—C13	124.39 (14)
H1A—C1—H1C	109.5	O3—C12—C11	115.54 (14)
H1B—C1—H1C	109.5	C13—C12—C11	120.08 (15)
N2—C2—C3	112.74 (13)	C14—C13—C12	119.65 (14)
N2—C2—Cl1	120.30 (11)	C14—C13—H13	120.2
C3—C2—Cl1	126.95 (12)	C12—C13—H13	120.2
C8—C3—C4	121.43 (13)	C13—C14—C9	120.33 (13)
C8—C3—C2	135.32 (14)	C13—C14—H14	119.8
C4—C3—C2	103.24 (13)	C9—C14—H14	119.8
N1—C4—C3	107.20 (13)	O3—C15—H15A	109.5
N1—C4—C5	131.85 (15)	O3—C15—H15B	109.5
C3—C4—C5	120.95 (14)	H15A—C15—H15B	109.5
C6—C5—C4	117.13 (15)	O3—C15—H15C	109.5
C6—C5—H5	121.4	H15A—C15—H15C	109.5
C4—C5—H5	121.4	H15B—C15—H15C	109.5
C5—C6—C7	122.58 (14)	N2—N1—C4	111.53 (13)
C5—C6—H6	118.7	N2—N1—C1	119.65 (15)
C7—C6—H6	118.7	C4—N1—C1	128.76 (15)
C8—C7—C6	120.47 (14)	C2—N2—N1	105.29 (12)
C8—C7—N3	123.47 (14)	C7—N3—S1	125.87 (10)
C6—C7—N3	115.98 (13)	C7—N3—H3N	116.4
C7—C8—C3	117.42 (14)	S1—N3—H3N	109.8
C7—C8—H8	121.3	C12—O3—C15	117.58 (15)
C3—C8—H8	121.3	O1—S1—O2	119.16 (7)
C14—C9—C10	120.00 (14)	O1—S1—N3	108.43 (7)
C14—C9—S1	119.80 (11)	O2—S1—N3	104.11 (7)
C10—C9—S1	120.20 (11)	O1—S1—C9	107.91 (7)
C11—C10—C9	119.45 (13)	O2—S1—C9	108.05 (7)
C11—C10—H10	120.3	N3—S1—C9	108.82 (7)
C9—C10—H10	120.3

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···O2ⁱ	0.89	2.04	2.9286 (17)	175
C5—H5···O3ⁱⁱ	0.93	2.56	3.426 (2)	156

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯O2ⁱ	0.89	2.04	2.9286 (17)	175
C5—H5⋯O3ⁱⁱ	0.93	2.56	3.426 (2)	156

Symmetry codes: (i) ; (ii) .

8 in total

1. A short history of SHELX.

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

Review 2. Anticancer and antiviral sulfonamides.

Authors: Andrea Scozzafava; Takashi Owa; Antonio Mastrolorenzo; Claudiu T Supuran
Journal: Curr Med Chem Date: 2003-06 Impact factor: 4.530

3. Synthesis of new sulfonamides as lipoxygenase inhibitors.

Authors: Ghulam Mustafa; Islam Ullah Khan; Muhammad Ashraf; Iftikhar Afzal; Sohail Anjum Shahzad; Muhammad Shafiq
Journal: Bioorg Med Chem Date: 2012-03-03 Impact factor: 3.641

4. Synthesis and antitumor activity of new sulfonamide derivatives of thiadiazolo[3,2-a]pyrimidines.

Authors: Nadia S El-Sayed; Eman R El-Bendary; Saadia M El-Ashry; Mohammed M El-Kerdawy
Journal: Eur J Med Chem Date: 2011-05-30 Impact factor: 6.514

5. Synthesis, antiproliferative and apoptotic activities of N-(6(4)-indazolyl)-benzenesulfonamide derivatives as potential anticancer agents.

Authors: Najat Abbassi; Hakima Chicha; El Mostapha Rakib; Abdellah Hannioui; Mdaghri Alaoui; Abdelouahed Hajjaji; Detlef Geffken; Cinzia Aiello; Rosaria Gangemi; Camillo Rosano; Maurizio Viale
Journal: Eur J Med Chem Date: 2012-09-17 Impact factor: 6.514