(2RS,4′RS)-3′-(3-Chloro-4-meth­oxy­phen­yl)-4′-phenyl-4′H-spiro­[indene-2,5′-isoxazol]-1(3H)-one ethanol monosolvate

Boughaleb, A.; Zouihri, H.; Gmouh, S.; Kerbal, A.; El yazidi, M.

doi:10.1107/S1600536811032636

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2434

doi:10.1107/S1600536811032636

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(2RS,4′RS)-3′-(3-Chloro-4-methoxyphenyl)-4′-phenyl-4′H-spiro[indene-2,5′-isoxazol]-1(3H)-one ethanol monosolvate

Adil Boughaleb,^a Hafid Zouihri,^b Said Gmouh,^c Abdelali Kerbal ^a and Mohamed El yazidi ^a ^*

^aDépartement de Chimie, Faculté des Sciences, Dhar Mehraz, BP 1796 Atlas, 30000 Fés, Morocco, ^bLaboratoires de Diffraction des Rayons X, Centre Nationale pour la Recherche Scientifique et Technique, Rabat, Morocco, and ^cCentre Nationale pour la Recherche Scientifique et Technique, Rabat, Morocco
^*Correspondence e-mail: elyazidimohamed@hotmail.com

(Received 14 June 2011; accepted 11 August 2011; online 27 August 2011)

The title compound, C₂₃H₁₇ClN₂O₃·C₂H₆O, is the stoichiometric 1:1 ethanol solvate of a racemic reaction product, which forms a conglomerate. The refined Flack parameter of 0.36 (3) indicates racemic twinning. In the structure, molecules are linked into zigzag chains by a series of intermolecular N—H⋯O and O—H⋯O hydrogen bonds.

Related literature

For general background to dipolar 1,3-cycloaddition reactions, see: Al Houari et al. (2010 ); Toth et al. (1999 ); El yazidi et al. (1994 ).

Experimental

Crystal data

C₂₃H₁₇ClN₂O₃·C₂H₆O
M_r = 450.90
Orthorhombic, P 2₁ 2₁ 2₁
a = 8.7112 (2) Å
b = 11.3051 (2) Å
c = 22.5913 (5) Å
V = 2224.81 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.21 mm⁻¹
T = 296 K
0.24 × 0.17 × 0.16 mm

Data collection

Bruker APEXII CCD diffractometer
13160 measured reflections
4757 independent reflections
3815 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.096
S = 1.06
4757 reflections
297 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.32 e Å⁻³
Absolute structure: Flack (1983 ); 1986 Friedel pairs
Flack parameter: 0.36 (3)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O4	0.88 (3)	2.12 (3)	2.906 (2)	149 (2)
O4—H4A⋯O2ⁱ	0.82	2.02	2.813 (2)	164
Symmetry code: (i) x+1, y, 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, New_Global_Publ_Block. DOI: 10.1107/S1600536811032636/fy2017sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811032636/fy2017Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811032636/fy2017Isup3.cml

checkCIF report

Comment top

In general, the 1,3-dipolar cycloaddition of arylnitrile oxides with ethylenic dipolarophiles leads to the regioselective formation of isoxazolines so that the electron withdrawing substituent of the dipolarophile is connected to position 5 of the isoxazoline ring (Al Houari et al., 2010; Toth et al., 1999; El yazidi et al., 1994).

The crystal structure shows that the carbonyl group is bonded to position 5 of the isoxazoline ring, and that the hydrogen atom in position 4 is situated on the same side of the ring as the carbonyl group. The structural study by X-rays is in perfect agreement with the results of IR, ¹H and ¹³C NMR spectroscopic analysis.

The 1,3-dipolar cycloaddition gave the title compound as a racemic product. However, the crystallization process from ethanol resulted in the formation of a conglomerate in space group P2₁2₁2₁.

In the crystal molecules are linked into zigzag chains by a series of intermolecular N—H···O and O—H···O hydrogen-bonding interactions, where both the main and the solvent molecules take part (Table 1).

Related literature top

For general background to dipolar 1,3-cycloaddition reactions, see: Al Houari et al. (2010); Toth et al. (1999); and El yazidi et al. (1994).

Experimental top

4 mmol of (2Z)-2-benzylidene-1,2-dihydro-3H-indol-3-one and 4 mmol of 3-chloro-N-hydroxy-4-methoxybenzenecarboximidoyl chloride were dissolved in 30 ml of THF in a 100 ml flask equipped with a condenser. The reaction mixture was refluxed until the complete dissolution of the reagents, and then 1 ml of N,N-diethylethanamine was added to the reaction. Monitoring the reaction by thin film chromatography revealed the formation of a single cycloaddition product. After filtration, the organic solution was evaporated under reduced pressure. The residue obtained was recrystallized from ethanol.

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 and O—H···O hydrogen bondings. H atoms not involved in hydrogen bonds have been omitted for clarity. Symmetry codes: (i) x+1, y, z.

(2RS,4'RS)-3'-(3-Chloro-4-methoxyphenyl)-4'-phenyl-4'H- spiro[indene-2,5'-isoxazol]-1(3H)-one ethanol monosolvate top

Crystal data top

C₂₃H₁₇ClN₂O₃·C₂H₆O	F(000) = 944
M_r = 450.90	D_x = 1.346 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 265 reflections
a = 8.7112 (2) Å	θ = 2.6–26.3°
b = 11.3051 (2) Å	µ = 0.21 mm⁻¹
c = 22.5913 (5) Å	T = 296 K
V = 2224.81 (8) Å³	Prism, colourless
Z = 4	0.24 × 0.17 × 0.16 mm

Data collection top

Bruker APEXII CCD diffractometer	3815 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.027
Graphite monochromator	θ_max = 27.0°, θ_min = 1.8°
ω and ϕ scans	h = −10→11
13160 measured reflections	k = −14→14
4757 independent reflections	l = −28→17

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.096	w = 1/[σ²(F_o²) + (0.0469P)² + 0.1284P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
4757 reflections	Δρ_max = 0.16 e Å⁻³
297 parameters	Δρ_min = −0.32 e Å⁻³
0 restraints	Absolute structure: Flack (1983); 1986 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.36 (3)

Crystal data top

C₂₃H₁₇ClN₂O₃·C₂H₆O	V = 2224.81 (8) Å³
M_r = 450.90	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 8.7112 (2) Å	µ = 0.21 mm⁻¹
b = 11.3051 (2) Å	T = 296 K
c = 22.5913 (5) Å	0.24 × 0.17 × 0.16 mm

Data collection top

Bruker APEXII CCD diffractometer	3815 reflections with I > 2σ(I)
13160 measured reflections	R_int = 0.027
4757 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.096	Δρ_max = 0.16 e Å⁻³
S = 1.06	Δρ_min = −0.32 e Å⁻³
4757 reflections	Absolute structure: Flack (1983); 1986 Friedel pairs
297 parameters	Absolute structure parameter: 0.36 (3)
0 restraints

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
C1	0.0305 (2)	0.33701 (16)	0.41709 (9)	0.0378 (4)
C10	0.1211 (2)	0.35087 (15)	0.26128 (8)	0.0333 (4)
C11	0.2714 (2)	0.39793 (16)	0.23651 (8)	0.0340 (4)
C12	0.3965 (2)	0.32367 (18)	0.22940 (10)	0.0470 (5)
C13	0.5324 (3)	0.3680 (2)	0.20606 (11)	0.0590 (6)
C14	0.5434 (3)	0.4828 (2)	0.18859 (11)	0.0629 (7)
C15	0.4190 (3)	0.5564 (2)	0.19482 (11)	0.0585 (6)
C16	0.2839 (2)	0.51488 (18)	0.21932 (10)	0.0471 (5)
C17	−0.0022 (2)	0.26234 (16)	0.16411 (8)	0.0359 (4)
C18	−0.0316 (3)	0.16313 (18)	0.12947 (10)	0.0533 (6)
C19	−0.0905 (3)	0.17326 (19)	0.07365 (11)	0.0613 (7)
C2	−0.0518 (3)	0.36087 (19)	0.46878 (10)	0.0495 (5)
C20	−0.1223 (3)	0.28381 (19)	0.04958 (10)	0.0526 (5)
C21	−0.0928 (2)	0.38300 (17)	0.08457 (9)	0.0423 (5)
C22	−0.0338 (2)	0.37289 (17)	0.14030 (9)	0.0379 (4)
C23	−0.2016 (4)	0.2016 (3)	−0.04206 (13)	0.0908 (10)
C24	0.6087 (4)	0.5038 (3)	0.36539 (16)	0.0920 (9)
C25	0.4781 (4)	0.5779 (3)	0.37505 (16)	0.1008 (11)
C3	0.0272 (3)	0.3874 (2)	0.51910 (10)	0.0587 (6)
C4	0.1875 (3)	0.3900 (2)	0.51872 (10)	0.0569 (6)
C5	0.2713 (3)	0.36897 (19)	0.46834 (9)	0.0466 (5)
C6	0.1917 (2)	0.34114 (16)	0.41674 (9)	0.0378 (4)
C7	0.1305 (2)	0.28684 (16)	0.32140 (8)	0.0362 (4)
C8	−0.0172 (2)	0.30244 (18)	0.35872 (9)	0.0389 (5)
C9	0.0618 (2)	0.24995 (15)	0.22427 (8)	0.0330 (4)
Cl1	−0.12367 (8)	0.52300 (5)	0.05494 (3)	0.06402 (19)
H1	0.346 (3)	0.324 (2)	0.3510 (10)	0.060 (7)*
H10	0.0447	0.4144	0.2630	0.040*
H12	0.3895	0.2445	0.2402	0.056*
H13	0.6170	0.3184	0.2023	0.071*
H14	0.6345	0.5113	0.1726	0.075*
H15	0.4257	0.6348	0.1825	0.070*
H16	0.2011	0.5659	0.2243	0.056*
H18	−0.0107	0.0884	0.1446	0.064*
H19	−0.1096	0.1055	0.0515	0.074*
H2	−0.1585	0.3587	0.4688	0.059*
H22	−0.0145	0.4406	0.1625	0.045*
H23A	−0.1057	0.1606	−0.0465	0.136*
H23B	−0.2379	0.2263	−0.0802	0.136*
H23C	−0.2756	0.1497	−0.0242	0.136*
H24A	0.6892	0.5250	0.3931	0.110*
H24B	0.6475	0.5166	0.3257	0.110*
H25A	0.3977	0.5561	0.3481	0.151*
H25B	0.5062	0.6590	0.3685	0.151*
H25C	0.4427	0.5684	0.4150	0.151*
H3	−0.0258	0.4038	0.5539	0.070*
H4	0.2392	0.4066	0.5538	0.068*
H4A	0.6442	0.3400	0.3634	0.105*
H5	0.3779	0.3732	0.4687	0.056*
N1	0.2497 (2)	0.31383 (17)	0.36182 (8)	0.0444 (4)
N2	0.07647 (17)	0.14773 (13)	0.24799 (7)	0.0391 (4)
O1	0.13828 (17)	0.16082 (11)	0.30525 (6)	0.0426 (3)
O2	−0.14510 (17)	0.28485 (15)	0.33873 (7)	0.0583 (4)
O3	−0.1799 (2)	0.30291 (14)	−0.00516 (8)	0.0716 (5)
O4	0.57042 (17)	0.38095 (16)	0.37275 (9)	0.0703 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0382 (11)	0.0361 (10)	0.0391 (11)	−0.0006 (8)	0.0064 (9)	0.0047 (8)
C10	0.0287 (9)	0.0337 (9)	0.0374 (10)	0.0030 (8)	0.0024 (8)	0.0008 (7)
C11	0.0332 (11)	0.0352 (9)	0.0336 (10)	−0.0031 (8)	0.0001 (8)	−0.0006 (8)
C12	0.0396 (12)	0.0441 (11)	0.0571 (13)	−0.0002 (9)	0.0087 (10)	−0.0001 (9)
C13	0.0373 (12)	0.0655 (15)	0.0741 (17)	−0.0016 (11)	0.0164 (12)	−0.0106 (13)
C14	0.0480 (14)	0.0782 (18)	0.0625 (16)	−0.0275 (13)	0.0121 (12)	0.0003 (13)
C15	0.0599 (16)	0.0500 (13)	0.0657 (16)	−0.0216 (11)	0.0001 (13)	0.0119 (11)
C16	0.0464 (12)	0.0387 (10)	0.0561 (13)	−0.0035 (9)	−0.0030 (11)	0.0045 (10)
C17	0.0311 (10)	0.0377 (10)	0.0390 (11)	−0.0025 (8)	−0.0014 (8)	−0.0013 (8)
C18	0.0685 (15)	0.0365 (11)	0.0549 (14)	−0.0078 (10)	−0.0150 (12)	0.0033 (10)
C19	0.0843 (19)	0.0429 (12)	0.0566 (15)	−0.0146 (11)	−0.0225 (13)	−0.0047 (10)
C2	0.0509 (13)	0.0523 (13)	0.0454 (12)	−0.0015 (10)	0.0150 (11)	0.0028 (10)
C20	0.0555 (13)	0.0545 (13)	0.0476 (13)	−0.0071 (11)	−0.0158 (12)	0.0031 (10)
C21	0.0380 (12)	0.0417 (10)	0.0472 (12)	0.0030 (8)	−0.0033 (10)	0.0048 (9)
C22	0.0344 (10)	0.0375 (10)	0.0417 (11)	0.0010 (8)	−0.0001 (9)	−0.0022 (8)
C23	0.129 (3)	0.0773 (18)	0.0661 (19)	−0.0205 (18)	−0.0483 (19)	−0.0026 (15)
C24	0.078 (2)	0.090 (2)	0.108 (3)	−0.0139 (19)	0.0090 (19)	−0.0018 (18)
C25	0.106 (3)	0.074 (2)	0.122 (3)	−0.0016 (19)	−0.005 (2)	0.0111 (19)
C3	0.0709 (18)	0.0657 (15)	0.0396 (13)	0.0004 (13)	0.0141 (12)	0.0017 (11)
C4	0.0744 (18)	0.0605 (14)	0.0357 (12)	0.0038 (12)	−0.0051 (11)	0.0001 (10)
C5	0.0484 (13)	0.0502 (12)	0.0413 (12)	0.0023 (10)	−0.0078 (10)	0.0075 (9)
C6	0.0410 (11)	0.0333 (9)	0.0392 (11)	0.0020 (8)	0.0030 (9)	0.0054 (8)
C7	0.0304 (10)	0.0396 (10)	0.0387 (10)	0.0008 (8)	0.0041 (9)	−0.0017 (8)
C8	0.0334 (12)	0.0391 (10)	0.0442 (12)	−0.0022 (8)	0.0066 (9)	0.0003 (9)
C9	0.0265 (9)	0.0351 (9)	0.0374 (10)	−0.0009 (7)	0.0052 (8)	0.0013 (8)
Cl1	0.0852 (4)	0.0498 (3)	0.0571 (3)	0.0136 (3)	−0.0127 (4)	0.0081 (3)
N1	0.0296 (10)	0.0642 (11)	0.0393 (10)	−0.0021 (8)	0.0047 (8)	−0.0020 (8)
N2	0.0414 (10)	0.0371 (9)	0.0389 (9)	−0.0005 (7)	0.0019 (7)	0.0001 (7)
O1	0.0502 (8)	0.0370 (7)	0.0405 (8)	0.0051 (6)	0.0008 (7)	0.0041 (6)
O2	0.0312 (9)	0.0843 (11)	0.0595 (10)	−0.0069 (7)	0.0045 (7)	−0.0158 (8)
O3	0.0952 (14)	0.0641 (10)	0.0555 (10)	−0.0077 (9)	−0.0353 (10)	−0.0004 (8)
O4	0.0398 (9)	0.0696 (12)	0.1014 (14)	−0.0027 (8)	0.0102 (9)	−0.0073 (10)

Geometric parameters (Å, º) top

C1—C2	1.397 (3)	C23—H23C	0.9600
C10—H10	0.9800	C23—H23B	0.9600
C10—C7	1.541 (3)	C23—H23A	0.9600
C10—C11	1.520 (2)	C24—H24B	0.9700
C10—C9	1.506 (2)	C24—H24A	0.9700
C11—C12	1.385 (3)	C24—C25	1.429 (5)
C11—C16	1.382 (3)	C25—H25C	0.9600
C12—H12	0.9300	C25—H25B	0.9600
C12—C13	1.389 (3)	C25—H25A	0.9600
C13—H13	0.9300	C3—H3	0.9300
C13—C14	1.361 (4)	C4—H4	0.9300
C14—H14	0.9300	C4—C3	1.396 (4)
C15—H15	0.9300	C4—C5	1.373 (3)
C15—C14	1.373 (4)	C5—H5	0.9300
C16—H16	0.9300	C6—C1	1.405 (3)
C16—C15	1.383 (3)	C6—C5	1.392 (3)
C17—C9	1.476 (3)	C8—C7	1.549 (3)
C17—C18	1.391 (3)	C8—C1	1.437 (3)
C18—H18	0.9300	N1—H1	0.88 (3)
C18—C19	1.366 (3)	N1—C7	1.416 (3)
C19—H19	0.9300	N1—C6	1.375 (3)
C2—H2	0.9300	N2—O1	1.409 (2)
C2—C3	1.362 (3)	N2—C9	1.280 (2)
C20—C19	1.391 (3)	O1—C7	1.472 (2)
C21—Cl1	1.739 (2)	O2—C8	1.218 (2)
C21—C20	1.396 (3)	O3—C23	1.429 (3)
C22—H22	0.9300	O3—C20	1.352 (3)
C22—C17	1.388 (3)	O4—H4A	0.8200
C22—C21	1.365 (3)	O4—C24	1.438 (4)

C6—C1—C8	107.05 (17)	H23A—C23—H23C	109.5
C2—C1—C8	132.17 (19)	O3—C23—H23C	109.5
C2—C1—C6	120.7 (2)	H23A—C23—H23B	109.5
C7—C10—H10	110.1	O3—C23—H23B	109.5
C11—C10—H10	110.1	O3—C23—H23A	109.5
C9—C10—H10	110.1	H24A—C24—H24B	108.0
C11—C10—C7	116.32 (16)	O4—C24—H24B	109.4
C9—C10—C7	98.72 (13)	C25—C24—H24B	109.4
C9—C10—C11	110.86 (15)	O4—C24—H24A	109.4
C12—C11—C10	120.54 (16)	C25—C24—H24A	109.4
C16—C11—C10	120.42 (17)	C25—C24—O4	111.3 (3)
C16—C11—C12	119.01 (17)	H25B—C25—H25C	109.5
C13—C12—H12	120.1	H25A—C25—H25C	109.5
C11—C12—H12	120.1	C24—C25—H25C	109.5
C11—C12—C13	119.73 (19)	H25A—C25—H25B	109.5
C12—C13—H13	119.5	C24—C25—H25B	109.5
C14—C13—H13	119.5	C24—C25—H25A	109.5
C14—C13—C12	120.9 (2)	C4—C3—H3	119.8
C15—C14—H14	120.2	C2—C3—H3	119.8
C13—C14—H14	120.2	C2—C3—C4	120.3 (2)
C13—C14—C15	119.5 (2)	C3—C4—H4	118.9
C16—C15—H15	119.8	C5—C4—H4	118.9
C14—C15—H15	119.8	C5—C4—C3	122.2 (2)
C14—C15—C16	120.4 (2)	C6—C5—H5	121.0
C15—C16—H16	119.8	C4—C5—H5	121.0
C11—C16—H16	119.8	C4—C5—C6	117.9 (2)
C11—C16—C15	120.3 (2)	C5—C6—C1	120.04 (19)
C18—C17—C9	120.73 (16)	N1—C6—C1	111.39 (18)
C22—C17—C9	121.14 (16)	N1—C6—C5	128.57 (18)
C22—C17—C18	118.13 (17)	C10—C7—C8	112.47 (16)
C17—C18—H18	119.3	O1—C7—C8	106.46 (14)
C19—C18—H18	119.3	N1—C7—C8	103.50 (15)
C19—C18—C17	121.38 (19)	O1—C7—C10	103.80 (14)
C20—C19—H19	119.6	N1—C7—C10	120.40 (16)
C18—C19—H19	119.6	N1—C7—O1	109.55 (15)
C18—C19—C20	120.74 (19)	C1—C8—C7	106.86 (16)
C1—C2—H2	120.6	O2—C8—C7	122.64 (18)
C3—C2—H2	120.6	O2—C8—C1	130.48 (19)
C3—C2—C1	118.7 (2)	C17—C9—C10	124.70 (15)
C19—C20—C21	117.63 (19)	N2—C9—C10	114.66 (16)
O3—C20—C21	117.26 (19)	N2—C9—C17	120.58 (16)
O3—C20—C19	125.11 (19)	C7—N1—H1	123.1 (15)
C20—C21—Cl1	118.99 (16)	C6—N1—H1	124.9 (15)
C22—C21—Cl1	119.30 (15)	C6—N1—C7	111.18 (17)
C22—C21—C20	121.64 (18)	C9—N2—O1	109.12 (14)
C17—C22—H22	119.8	N2—O1—C7	108.16 (12)
C21—C22—H22	119.8	C20—O3—C23	117.03 (19)
C21—C22—C17	120.49 (18)	C24—O4—H4A	109.5
H23B—C23—H23C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4	0.88 (3)	2.12 (3)	2.906 (2)	149 (2)
O4—H4A···O2ⁱ	0.82	2.02	2.813 (2)	164

Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₃H₁₇ClN₂O₃·C₂H₆O
M_r	450.90
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	8.7112 (2), 11.3051 (2), 22.5913 (5)
V (Å³)	2224.81 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.21
Crystal size (mm)	0.24 × 0.17 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	13160, 4757, 3815
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.096, 1.06
No. of reflections	4757
No. of parameters	297
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.32
Absolute structure	Flack (1983); 1986 Friedel pairs
Absolute structure parameter	0.36 (3)

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

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O4	0.88 (3)	2.12 (3)	2.906 (2)	149 (2)
O4—H4A···O2ⁱ	0.8200	2.0200	2.813 (2)	164.00

Symmetry code: (i) x+1, y, z.

Acknowledgements

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

References

Al Houari, G., Bennani, A. K., Bennani, B., Daoudi, M., Benlarbi, N., El Yazidi, M., Garrigues, B. & Kerbal, A. (2010). J. Maroc. Chim. Heterocycl. 9, 36–43. CAS Google Scholar
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
El yazidi, M., Daou, B., Bougrin, K. & Soufiaoui, M. (1994). J. Soc. Maroc. Chim. 3, 54–51. Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Toth, G., Balazs, B., Levai, A., Fisera, L. & Jedlovska, E. (1999). J. Mol. Struct. 508, 29–36. Web of Science CrossRef CAS 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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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

(2RS,4′RS)-3′-(3-Chloro-4-meth­­oxy­phen­yl)-4′-phenyl-4′H-spiro­[indene-2,5′-isoxazol]-1(3H)-one ethanol monosolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

(2RS,4′RS)-3′-(3-Chloro-4-methoxyphenyl)-4′-phenyl-4′H-spiro[indene-2,5′-isoxazol]-1(3H)-one ethanol monosolvate