N-[7-Eth­oxy-1-(prop-2-en-1-yl)-1H-indazol-4-yl]-4-methyl­benzene­sulfonamide

Abbassi, N.; Rakib, E.M.; Zouihri, H.

doi:10.1107/S1600536811019465

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1561

doi:10.1107/S1600536811019465

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N-[7-Ethoxy-1-(prop-2-en-1-yl)-1H-indazol-4-yl]-4-methylbenzenesulfonamide

Najat Abbassi,^a El Mostapha Rakib ^a ^* and Hafid Zouihri ^b

^aLaboratoire de Chimie Organique et Analytique, Université Sultan Moulay Slimane, Faculté des Sciences et Techniques, Béni-Mellal, BP 523, Morocco, and ^bLaboratoires de Diffraction des Rayons X, Centre Nationale pour la Recherche Scientifique et Technique, Rabat, Morocco
^*Correspondence e-mail: elmostapha1@ymail.com

(Received 11 May 2011; accepted 23 May 2011; online 4 June 2011)

In the title compound, C₁₉H₂₁N₃O₃S, the C—SO₂—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 methylbenzene 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 tetrahedral geometry [maximum deviation: O—S—O = 119.18 (11)°]. An intramolecular C—H⋯O hydrogen bond occurs. In the crystal, two molecules are linked about a center of inversion by pairs of N—H⋯O hydrogen bonds, generating a dimer. C—H⋯π interactions are also observed.

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_r = 371.45
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.042
wR(F²) = 0.118
S = 1.08
3629 reflections
259 parameters
6 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.39 e Å⁻³
Δρ_min = −0.32 e Å⁻³

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) -x, -y+1, -z+1; (ii) -x, -y+1, -z.

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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811019465/ng5164sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811019465/ng5164Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811019465/ng5164Isup3.cml

checkCIF report

Comment top

Various sulfonamides are widely used as anti-hypertensive [Soledade et al., 2006; Lee & Lee, 2002]. In a former paper, we reported the crystal structure of N-(7-ethoxy-1H-indazol-4-yl)-4-methylbenzenesulfonamide [Abbassi et al., 2011b]. In this communication, the crystal structure of N-[7-ethoxy-1-(prop-2-en-1-yl)-1H-indazol-4-yl]-4-methylbenzenesulfonamide is reported.

The title heterocyclic compound, C₁₉H₂₁N₃O₃S, is a new synthetic molecule whish is bent at the S atom with an C—SO~2~—NH—C torsion angle of 103.72 (11)°. The indazol planar ring [r.m.s. deviation: 0.0202 (14) Å] is twisted away from the methylbenzene ring by 76.87 (7)°. The vinyl group is disordered over two positions with site occupancies of 0.622 (10) and 0.378 (10). The S atom has a distorted tetrahedral geometry [maximum deviation: O—S—O = 119.17 (10)°].

In the crystal structure, the molecules are linked by N—H···O hydrogen bonds together with weak C—H···O interactions. There also exist C—H···Cg contacts between the methyl groups of the methylbenzene and the indazol rings. The crystal structure is further stabilized by intermolecular π–π stacking interactions [centroid–centroid distances = 3.6673 (9)–3.8109 (10) A °].

Related literature top

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 top

A mixture of 1-allyl-4-nitro-1H-indazole [Abbassi et al., 2011a] (1.22 mmol) and anhydrous SnCl₂ (1.1 g, 6.1 mmol) in 25 mL of absolute ethanol was heated at 60 °C for 2 h. After reduction, the starting material disappeared, and the solution was allowed to cool down. The pH was made slightly basic (pH 7–8) by addition of 5% aqueous potassium bicarbonate before extraction with ethyl acetate. The organic phase was washed with brine and dried over magnesium sulfate. The solvent was removed to afford the amine, which was immediately dissolved in pyridine (5 ml) and then reacted with 4-methylbenzenesulfonyl chloride (0.26 g, 1.25 mmol) at room temperature for 24 h. After the reaction mixture was concentrated in vacuo, the resulting residue was purified by flash chromatography (eluted with Ethyl acetate: Hexane 1:9).

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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).

Figures top

	Fig. 1. Molecular view of the title compound showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Partial packing view showing the chain formed by N—H···O. H atoms not involved in hydrogen bonds have been omitted for clarity.

N-[7-Ethoxy-1-(prop-2-en-1-yl)-1H-indazol-4-yl]-4- methylbenzenesulfonamide top

Crystal data top

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

Data collection top

Bruker APEXII CCD detector diffractometer	3281 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.023
Graphite monochromator	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 top

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

Crystal data top

C₁₉H₂₁N₃O₃S	γ = 107.500 (2)°
M_r = 371.45	V = 921.33 (6) Å³
Triclinic, P1	Z = 2
a = 8.2208 (3) Å	Mo Kα radiation
b = 10.4985 (4) Å	µ = 0.20 mm⁻¹
c = 11.9655 (5) Å	T = 296 K
α = 108.814 (2)°	0.32 × 0.17 × 0.12 mm
β = 92.346 (2)°

Data collection top

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

Refinement top

R[F² > 2σ(F²)] = 0.042	6 restraints
wR(F²) = 0.118	H atoms treated by a mixture of independent and constrained refinement
S = 1.08	Δρ_max = 0.39 e Å⁻³
3629 reflections	Δρ_min = −0.32 e Å⁻³
259 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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

Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₁₉H₂₁N₃O₃S
M_r	371.45
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.2208 (3), 10.4985 (4), 11.9655 (5)
α, β, γ (°)	108.814 (2), 92.346 (2), 107.500 (2)
V (Å³)	921.33 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.20
Crystal size (mm)	0.32 × 0.17 × 0.12

Data collection
Diffractometer	Bruker APEXII CCD detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	23139, 3629, 3281
R_int	0.023
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.118, 1.08
No. of reflections	3629
No. of parameters	259
No. of restraints	6
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.32

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

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) −x, −y+1, −z+1; (ii) −x, −y+1, −z.

Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.

References

Abbassi, N., Rakib, E. M., Hannioui, A., Alaoui, M., Benchidmi, M., Essassi, E. M. & Geffken, D. (2011a). Heterocycles, 83, 891–900. CAS Google Scholar
Abbassi, N., Rakib, E. M. & Zouihri, H. (2011b). Acta Cryst. E67, o1354. Web of Science CSD CrossRef IUCr Journals Google Scholar
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Lee, J. S. & Lee, C. H. (2002). Bull. Korean Chem. Soc. 23, 167–169. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Soledade, M., Pedras, C. & Jha, M. (2006). Bioorg. Med. Chem. 14, 4958–4979. Web of Science PubMed Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 67| Part 7| July 2011| Page o1561

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