3,5-Bis(4-meth­oxy­phen­yl)-4,5-dihydro­isoxazole

Samshuddin, S.; Butcher, R.J.; Akkurt, M.; Narayana, B.; Yathirajan, H.S.

doi:10.1107/S1600536811026833

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Pages o1975-o1976

doi:10.1107/S1600536811026833

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3,5-Bis(4-methoxyphenyl)-4,5-dihydroisoxazole

S. Samshuddin,^a Ray J. Butcher,^b Mehmet Akkurt,^c ^* B. Narayana ^a and H. S. Yathirajan ^d

^aDepartment of Studies in Chemistry, Mangalore University, Mangalagangotri 574 199, India, ^bDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, ^cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and ^dDepartment of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore 570 006, India
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 22 June 2011; accepted 5 July 2011; online 9 July 2011)

In the title compound, C₁₇H₁₇NO₃, the five-membered isoxazoline ring adopts an envelope conformation with the chiral C atom at the flap position and 0.133 (2) Å out of the mean plane formed by the other four atoms. The two benzene rings form dihedral angles of 6.05 (5) and 81.52 (5)° with the C—C—N—O plane of the isoxazoline ring. The crystal structure is stabilized by weak C—H⋯O hydrogen bonds and C—H⋯π interactions.

Related literature

For medical uses of isoxazole derivatives, see: Sperry & Wright (2005 ). For their biological activity, see; Boyd (1991 ); Lang & Lin (1984 ). For related structures, see; Baktır et al. (2011a ,b ); Chopra et al. (2006 ); Dardouri et al. (2010 ); Fun et al. (2010a ,b ); Guo et al. (2006 ); Jasinski et al. (2010 ); Ko et al. (2011 ); Samshuddin et al. (2010 ). For ring puckering and asymmetry parameters, see: Cremer & Pople (1975 ); Nardelli (1983 ).

Experimental

Crystal data

C₁₇H₁₇NO₃
M_r = 283.32
Orthorhombic, P b c a
a = 10.5071 (7) Å
b = 8.4023 (5) Å
c = 32.6662 (19) Å
V = 2883.9 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 295 K
0.42 × 0.36 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ) T_min = 0.967, T_max = 1.000
13952 measured reflections
4821 independent reflections
2738 reflections with i > 2σ(i)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.075
wR(F²) = 0.156
S = 1.06
4821 reflections
192 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C1A–C6A and C1B–C6B benzene rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6A—H6AA⋯O1ⁱ	0.93	2.52	3.324 (2)	145
C1—H1A⋯Cg3ⁱⁱ	0.98	2.62	3.590 (2)	170
C6B—H6BA⋯Cg3ⁱⁱⁱ	0.93	3.00	3.724 (2)	136
C7B—H7BC⋯Cg2^iv	0.96	2.83	3.541 (3)	132
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) -x+1, -y+1, -z+1; (iii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, z]$ ; (iv) -x+1, -y+2, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2007 $[Oxford Diffraction (2007). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ); 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, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811026833/im2301sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811026833/im2301Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811026833/im2301Isup3.cml

checkCIF report

Comment top

Chalcones are convenient intermediates for the synthesis of various biodynamic cyclic derivatives such as isoxazoline, pyrazoline, benzodiazepine and cyclohexenone derivatives (Samshuddin et al., 2010; Fun et al., 2010a,b; Jasinski et al., 2010; Baktır et al., 2011a,b). Isoxazole derivatives represent a unique class of nitrogen- and oxygen-containing five-membered heterocycles. These are the components in a variety of natural products and medicinally useful compounds (Sperry et al., 2005). Isoxazole derivatives bearing different substituents are known to have various biological activities in pharmaceutical and agricultural areas (Lang & Lin, 1984; Boyd, 1991).

The crystal structures of some 4,5-dihydroisoxazole derivatives viz., 5-(4-fluoro-3-phenoxyphenyl)-3-(4-methylphenyl)-4,5-dihydroisoxazole (Chopra et al., 2006), 5-(1H-indol-3-yl)-3-(4-methylphenyl)-4,5-dihydroisoxazoline (Guo et al., 2006), 1,5-dimethyl-3-[(3-phenyl-4,5-dihydro-1,2-oxazol-5-yl)methyl]-1H-1,5- benzodiazepine-2,4(3H,5H)-dione (Dardouri et al., 2010) and (S)-[5-methyl-3-(3-methylthiophen-2-yl)-4,5-dihydroisoxazol-5-yl] methanol solvate (Ko et al., 2011) have been reported. In view of the importance of isoxazoles and in continuation of our work on synthesis of various derivatives of chalcones, the title compound (I) was prepared and its crystal structure is reported.

As shown in Fig. 1, the 4,5-dihydroisoxazole ring (O1/N1/C1–C3) of the title compound (I) has an envelope conformation with the chiral C1 atom at the flap position, displaced from the mean plane by -0.133 (2) Å; the puckering parameters (Cremer & Pople, 1975) are Q(2) = 0.2156 (17) Å, ϕ(2) = 319.7 (5)°. Furthermore, one (O1B/C1B–C7B) of the methoxyphenyl ring systems makes a dihedral angle of 6.05 (5)°, whereas the other one (O1A/C1A–C7A) is almost orthogonal to the plane formed by the four atoms O1, N1, C2 and C3 of the five-membered isoxazoline ring, the dihedral angle being 81.52 (5)° (Nardelli, 1983). The dihedral angle between the methoxyphenyl ring systems (O1A/C1A–C7A and O1B/C1B–C7B) is 76.56 (4)°.

In the crystal structure, molecules are linked by weak C6A—H6AA···O1 (Table 1, Fig. 2) hydrogen bonds, and are further consolidated by C–H···π interactions (Table 1, Cg2 and Cg3 are the centroids of the C1A–C6A and C1B–C6B benzene rings, respectively).

Related literature top

For medical uses of isoxazole derivatives, see: Sperry et al. (2005). For their biological activity, see; Boyd (1991); Lang & Lin (1984). For related structures, see; Baktır et al. (2011a,b); Chopra et al. (2006); Dardouri et al. (2010); Fun et al. (2010a,b); Guo et al. (2006); Jasinski et al. (2010); Ko et al. (2011); Samshuddin et al. (2010). For ring puckering and asymmetry parameters, see: Cremer & Pople (1975); Nardelli (1983).

Experimental top

A solution of (2E)-1,3-bis(4-methoxyphenyl)prop-2-en-1-one (2.68 g, 0.01 mol) and hydroxylamine hydrochloride (0.695 g, 0.01 mol) in 25 ml ethanol containing 3 ml of 10% sodium hydroxide solution was refluxed for 12 h. After cooling the mixture was poured into 50 ml ice-cold water. The resulting precipitate was collected by filtration and purified by recrystallization from ethanol. The single-crystal was grown from 2-propanol by slow evaporation of the solvent (yield: 59%; (m.p.: 407 K).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2007); cell refinement: CrysAlis PRO (Oxford Diffraction, 2007); data reduction: CrysAlis RED (Oxford Diffraction, 2007); 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, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. Molecular structure of the title compound with ellipsoids drawn at the 30% probability level and H atoms as spheres of arbitrary radius.
	Fig. 2. Packing diagram of the title molecule, showing C—H···O interactions, viewed down the b axis. Hydrogen atoms not involved in H-bonding have been omitted for clarity.

3,5-Bis(4-methoxyphenyl)-4,5-dihydroisoxazole top

Crystal data top

C₁₇H₁₇NO₃	F(000) = 1200
M_r = 283.32	D_x = 1.305 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 2593 reflections
a = 10.5071 (7) Å	θ = 5.2–32.6°
b = 8.4023 (5) Å	µ = 0.09 mm⁻¹
c = 32.6662 (19) Å	T = 295 K
V = 2883.9 (3) Å³	Triangular plate, colourless
Z = 8	0.42 × 0.36 × 0.16 mm

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	4821 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2738 reflections with i > 2σ(i)
Graphite monochromator	R_int = 0.046
Detector resolution: 10.5081 pixels mm^-1	θ_max = 32.7°, θ_min = 5.2°
ω scans	h = −12→15
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	k = −10→12
T_min = 0.967, T_max = 1.000	l = −29→46
13952 measured reflections

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)] = 0.075	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.156	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0468P)² + 0.4739P] where P = (F_o² + 2F_c²)/3
4821 reflections	(Δ/σ)_max = 0.001
192 parameters	Δρ_max = 0.23 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₇H₁₇NO₃	V = 2883.9 (3) Å³
M_r = 283.32	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 10.5071 (7) Å	µ = 0.09 mm⁻¹
b = 8.4023 (5) Å	T = 295 K
c = 32.6662 (19) Å	0.42 × 0.36 × 0.16 mm

Data collection top

Oxford Diffraction Xcalibur Ruby Gemini diffractometer	4821 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)	2738 reflections with i > 2σ(i)
T_min = 0.967, T_max = 1.000	R_int = 0.046
13952 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.075	0 restraints
wR(F²) = 0.156	H-atom parameters constrained
S = 1.06	Δρ_max = 0.23 e Å⁻³
4821 reflections	Δρ_min = −0.17 e Å⁻³
192 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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
O1	0.70804 (13)	0.51832 (16)	0.43065 (4)	0.0604 (5)
O1A	0.63367 (15)	0.77980 (18)	0.25241 (4)	0.0702 (5)
O1B	0.62961 (12)	0.83077 (16)	0.65053 (4)	0.0603 (5)
N1	0.72185 (15)	0.54460 (19)	0.47317 (4)	0.0554 (5)
C1	0.58593 (17)	0.5848 (2)	0.41763 (5)	0.0480 (6)
C1A	0.59901 (16)	0.6424 (2)	0.37429 (5)	0.0424 (5)
C1B	0.63231 (14)	0.69607 (18)	0.52798 (5)	0.0381 (5)
C2	0.55553 (17)	0.7045 (2)	0.45099 (5)	0.0487 (6)
C2A	0.51887 (17)	0.5861 (2)	0.34384 (6)	0.0534 (6)
C2B	0.53722 (15)	0.7969 (2)	0.54218 (5)	0.0420 (5)
C3	0.63763 (14)	0.64427 (19)	0.48509 (5)	0.0392 (5)
C3A	0.53294 (18)	0.6342 (2)	0.30376 (6)	0.0588 (7)
C3B	0.53190 (15)	0.8445 (2)	0.58282 (5)	0.0440 (5)
C4A	0.62771 (17)	0.7403 (2)	0.29317 (5)	0.0476 (6)
C4B	0.62455 (15)	0.7929 (2)	0.60983 (5)	0.0435 (5)
C5A	0.70837 (17)	0.7983 (2)	0.32303 (5)	0.0485 (6)
C5B	0.71995 (16)	0.6916 (2)	0.59621 (5)	0.0502 (6)
C6A	0.69329 (16)	0.7490 (2)	0.36319 (5)	0.0472 (5)
C6B	0.72320 (15)	0.6433 (2)	0.55609 (5)	0.0459 (6)
C7A	0.7369 (2)	0.8744 (3)	0.23880 (6)	0.0751 (9)
C7B	0.53076 (19)	0.9273 (3)	0.66684 (6)	0.0651 (8)
H2AA	0.45450	0.51470	0.35060	0.0640*
H1A	0.52180	0.50020	0.41830	0.0580*
H3AA	0.47830	0.59510	0.28370	0.0710*
H2A	0.57900	0.81170	0.44300	0.0580*
H2B	0.46610	0.70220	0.45830	0.0580*
H5AA	0.77240	0.87000	0.31620	0.0580*
H6AA	0.74780	0.78840	0.38320	0.0570*
H7AA	0.73380	0.88390	0.20950	0.1130*
H7AB	0.81560	0.82520	0.24670	0.1130*
H7AC	0.73120	0.97830	0.25090	0.1130*
H2BA	0.47560	0.83330	0.52400	0.0500*
H3BA	0.46660	0.91050	0.59180	0.0530*
H5BA	0.78200	0.65630	0.61440	0.0600*
H6BA	0.78700	0.57420	0.54750	0.0550*
H7BA	0.54280	0.93930	0.69580	0.0980*
H7BB	0.45000	0.87780	0.66170	0.0980*
H7BC	0.53280	1.03010	0.65400	0.0980*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0765 (9)	0.0589 (8)	0.0457 (7)	0.0266 (7)	0.0012 (6)	−0.0037 (6)
O1A	0.0859 (10)	0.0801 (10)	0.0445 (8)	−0.0125 (8)	−0.0025 (7)	0.0053 (7)
O1B	0.0668 (8)	0.0680 (9)	0.0461 (7)	0.0106 (7)	−0.0018 (6)	−0.0049 (6)
N1	0.0640 (10)	0.0565 (10)	0.0458 (8)	0.0209 (8)	0.0000 (7)	0.0006 (7)
C1	0.0512 (10)	0.0445 (10)	0.0484 (10)	−0.0028 (8)	−0.0005 (8)	0.0025 (7)
C1A	0.0459 (9)	0.0381 (9)	0.0433 (9)	0.0013 (7)	0.0011 (7)	−0.0018 (7)
C1B	0.0353 (8)	0.0358 (8)	0.0431 (9)	−0.0013 (7)	0.0019 (7)	0.0057 (6)
C2	0.0467 (9)	0.0551 (11)	0.0442 (9)	0.0109 (8)	0.0026 (7)	0.0033 (8)
C2A	0.0503 (10)	0.0533 (11)	0.0565 (11)	−0.0148 (9)	−0.0028 (8)	0.0009 (8)
C2B	0.0387 (8)	0.0410 (9)	0.0463 (9)	0.0046 (7)	−0.0007 (7)	0.0084 (7)
C3	0.0371 (8)	0.0354 (8)	0.0452 (9)	−0.0005 (7)	0.0028 (7)	0.0051 (6)
C3A	0.0607 (12)	0.0630 (12)	0.0528 (11)	−0.0120 (10)	−0.0144 (9)	−0.0034 (9)
C3B	0.0428 (9)	0.0387 (9)	0.0504 (10)	0.0047 (7)	0.0067 (7)	0.0044 (7)
C4A	0.0534 (10)	0.0480 (10)	0.0413 (9)	0.0038 (9)	0.0011 (7)	−0.0012 (7)
C4B	0.0462 (9)	0.0427 (9)	0.0417 (9)	−0.0033 (8)	0.0020 (7)	0.0031 (7)
C5A	0.0493 (10)	0.0458 (10)	0.0505 (10)	−0.0062 (8)	0.0029 (8)	0.0004 (7)
C5B	0.0439 (10)	0.0568 (11)	0.0500 (10)	0.0083 (8)	−0.0081 (7)	0.0044 (8)
C6A	0.0482 (9)	0.0480 (10)	0.0454 (9)	−0.0055 (8)	−0.0050 (7)	−0.0055 (7)
C6B	0.0384 (9)	0.0483 (10)	0.0511 (10)	0.0087 (8)	0.0017 (7)	0.0024 (8)
C7A	0.0860 (16)	0.0809 (16)	0.0584 (13)	−0.0076 (13)	0.0103 (11)	0.0144 (11)
C7B	0.0696 (13)	0.0732 (14)	0.0524 (12)	0.0015 (11)	0.0105 (9)	−0.0100 (10)

Geometric parameters (Å, º) top

O1—N1	1.4139 (19)	C4B—C5B	1.388 (2)
O1—C1	1.463 (2)	C5A—C6A	1.385 (2)
O1A—C4A	1.374 (2)	C5B—C6B	1.372 (2)
O1A—C7A	1.416 (3)	C1—H1A	0.9800
O1B—C4B	1.368 (2)	C2—H2A	0.9700
O1B—C7B	1.421 (3)	C2—H2B	0.9700
N1—C3	1.279 (2)	C2A—H2AA	0.9300
C1—C1A	1.503 (2)	C2B—H2BA	0.9300
C1—C2	1.517 (2)	C3A—H3AA	0.9300
C1A—C2A	1.386 (2)	C3B—H3BA	0.9300
C1A—C6A	1.384 (2)	C5A—H5AA	0.9300
C1B—C2B	1.390 (2)	C5B—H5BA	0.9300
C1B—C3	1.468 (2)	C6A—H6AA	0.9300
C1B—C6B	1.397 (2)	C6B—H6BA	0.9300
C2—C3	1.497 (2)	C7A—H7AA	0.9600
C2A—C3A	1.378 (3)	C7A—H7AB	0.9600
C2B—C3B	1.388 (2)	C7A—H7AC	0.9600
C3A—C4A	1.381 (3)	C7B—H7BA	0.9600
C3B—C4B	1.384 (2)	C7B—H7BB	0.9600
C4A—C5A	1.381 (2)	C7B—H7BC	0.9600

N1—O1—C1	108.43 (13)	C1—C2—H2A	112.00
C4A—O1A—C7A	118.35 (15)	C1—C2—H2B	112.00
C4B—O1B—C7B	117.94 (14)	C3—C2—H2A	112.00
O1—N1—C3	109.29 (14)	C3—C2—H2B	112.00
O1—C1—C1A	108.47 (14)	H2A—C2—H2B	109.00
O1—C1—C2	103.24 (13)	C1A—C2A—H2AA	119.00
C1A—C1—C2	118.86 (14)	C3A—C2A—H2AA	119.00
C1—C1A—C2A	120.70 (15)	C1B—C2B—H2BA	119.00
C1—C1A—C6A	121.39 (15)	C3B—C2B—H2BA	119.00
C2A—C1A—C6A	117.88 (15)	C2A—C3A—H3AA	120.00
C2B—C1B—C3	121.78 (14)	C4A—C3A—H3AA	120.00
C2B—C1B—C6B	117.75 (15)	C2B—C3B—H3BA	120.00
C3—C1B—C6B	120.47 (14)	C4B—C3B—H3BA	120.00
C1—C2—C3	100.90 (13)	C4A—C5A—H5AA	120.00
C1A—C2A—C3A	121.09 (16)	C6A—C5A—H5AA	120.00
C1B—C2B—C3B	121.60 (15)	C4B—C5B—H5BA	120.00
N1—C3—C1B	120.73 (14)	C6B—C5B—H5BA	120.00
N1—C3—C2	113.17 (14)	C1A—C6A—H6AA	119.00
C1B—C3—C2	126.01 (14)	C5A—C6A—H6AA	119.00
C2A—C3A—C4A	120.32 (17)	C1B—C6B—H6BA	120.00
C2B—C3B—C4B	119.44 (15)	C5B—C6B—H6BA	119.00
O1A—C4A—C3A	115.58 (16)	O1A—C7A—H7AA	109.00
O1A—C4A—C5A	124.85 (16)	O1A—C7A—H7AB	109.00
C3A—C4A—C5A	119.57 (16)	O1A—C7A—H7AC	109.00
O1B—C4B—C3B	125.04 (15)	H7AA—C7A—H7AB	109.00
O1B—C4B—C5B	115.21 (14)	H7AA—C7A—H7AC	109.00
C3B—C4B—C5B	119.72 (15)	H7AB—C7A—H7AC	110.00
C4A—C5A—C6A	119.56 (16)	O1B—C7B—H7BA	109.00
C4B—C5B—C6B	120.35 (15)	O1B—C7B—H7BB	109.00
C1A—C6A—C5A	121.58 (16)	O1B—C7B—H7BC	109.00
C1B—C6B—C5B	121.12 (15)	H7BA—C7B—H7BB	110.00
O1—C1—H1A	109.00	H7BA—C7B—H7BC	109.00
C1A—C1—H1A	109.00	H7BB—C7B—H7BC	109.00
C2—C1—H1A	109.00

C1—O1—N1—C3	−12.91 (18)	C2B—C1B—C3—N1	−176.15 (16)
N1—O1—C1—C1A	148.33 (13)	C2B—C1B—C3—C2	7.6 (2)
N1—O1—C1—C2	21.37 (16)	C6B—C1B—C3—N1	3.2 (2)
C7A—O1A—C4A—C3A	−173.31 (17)	C6B—C1B—C3—C2	−173.08 (15)
C7A—O1A—C4A—C5A	6.5 (3)	C2B—C1B—C6B—C5B	−1.1 (2)
C7B—O1B—C4B—C3B	1.7 (3)	C3—C1B—C6B—C5B	179.54 (15)
C7B—O1B—C4B—C5B	−176.75 (16)	C1—C2—C3—N1	14.78 (19)
O1—N1—C3—C1B	−178.53 (14)	C1—C2—C3—C1B	−168.71 (15)
O1—N1—C3—C2	−1.81 (19)	C1A—C2A—C3A—C4A	−0.1 (3)
O1—C1—C1A—C2A	123.44 (17)	C1B—C2B—C3B—C4B	1.2 (2)
O1—C1—C1A—C6A	−54.6 (2)	C2A—C3A—C4A—O1A	179.75 (16)
C2—C1—C1A—C2A	−119.19 (18)	C2A—C3A—C4A—C5A	−0.1 (3)
C2—C1—C1A—C6A	62.8 (2)	C2B—C3B—C4B—O1B	−179.72 (15)
O1—C1—C2—C3	−20.68 (16)	C2B—C3B—C4B—C5B	−1.4 (2)
C1A—C1—C2—C3	−140.76 (15)	O1A—C4A—C5A—C6A	−179.71 (16)
C1—C1A—C2A—C3A	−177.79 (16)	C3A—C4A—C5A—C6A	0.1 (3)
C6A—C1A—C2A—C3A	0.3 (3)	O1B—C4B—C5B—C6B	178.89 (15)
C1—C1A—C6A—C5A	177.80 (16)	C3B—C4B—C5B—C6B	0.4 (3)
C2A—C1A—C6A—C5A	−0.2 (3)	C4A—C5A—C6A—C1A	0.0 (3)
C3—C1B—C2B—C3B	179.44 (15)	C4B—C5B—C6B—C1B	0.9 (3)
C6B—C1B—C2B—C3B	0.1 (2)

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C1A–C6A and C1B–C6B benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C6A—H6AA···O1ⁱ	0.93	2.52	3.324 (2)	145
C1—H1A···Cg3ⁱⁱ	0.98	2.62	3.590 (2)	170
C6B—H6BA···Cg3ⁱⁱⁱ	0.93	3.00	3.724 (2)	136
C7B—H7BC···Cg2^iv	0.96	2.83	3.541 (3)	132

Symmetry codes: (i) −x+3/2, y+1/2, z; (ii) −x+1, −y+1, −z+1; (iii) −x+3/2, y−1/2, z; (iv) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₇NO₃
M_r	283.32
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	295
a, b, c (Å)	10.5071 (7), 8.4023 (5), 32.6662 (19)
V (Å³)	2883.9 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.42 × 0.36 × 0.16

Data collection
Diffractometer	Oxford Diffraction Xcalibur Ruby Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2007)
T_min, T_max	0.967, 1.000
No. of measured, independent and observed [i > 2σ(i)] reflections	13952, 4821, 2738
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.760

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.075, 0.156, 1.06
No. of reflections	4821
No. of parameters	192
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.17

Computer programs: CrysAlis PRO (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

Cg2 and Cg3 are the centroids of the C1A–C6A and C1B–C6B benzene rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C6A—H6AA···O1ⁱ	0.93	2.52	3.324 (2)	145
C1—H1A···Cg3ⁱⁱ	0.98	2.62	3.590 (2)	170
C6B—H6BA···Cg3ⁱⁱⁱ	0.93	3.00	3.724 (2)	136
C7B—H7BC···Cg2^iv	0.96	2.83	3.541 (3)	132

Symmetry codes: (i) −x+3/2, y+1/2, z; (ii) −x+1, −y+1, −z+1; (iii) −x+3/2, y−1/2, z; (iv) −x+1, −y+2, −z+1.

Acknowledgements

SS and BN thank Mangalore University for the research facilities and the UGC SAP for financial assistance for the purchase of chemicals. RJB wishes to acknowledge the NSF–MRI program (grant CHE-0619278) for funds to purchase the diffractometer.

References

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Volume 67| Part 8| August 2011| Pages o1975-o1976

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