3-(6-Benz­yloxy-2,2-dimethyl­perhydro­furo[2,3-d][1,3]dioxolan-5-yl)-5-(4-chloro­phen­yl)-4-nitro-2-phenyl-2,3,4,5-tetra­hydro­isoxazole

NizamMohideen, M.; Damodiran, M.; SubbiahPandi, A.; Perumal, P.T.

doi:10.1107/S1600536809034096

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Pages o2305-o2306

doi:10.1107/S1600536809034096

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3-(6-Benzyloxy-2,2-dimethylperhydrofuro[2,3-d][1,3]dioxolan-5-yl)-5-(4-chlorophenyl)-4-nitro-2-phenyl-2,3,4,5-tetrahydroisoxazole

M. NizamMohideen,^a M. Damodiran,^b A. SubbiahPandi ^c ^* and P. T. Perumal ^b

^aDepartment of Physics, The New College (Autonomous), Chennai 600 014, India, ^bOrganic Chemistry Division, Central Leather Research Institute, Chennai 600 020, India, and ^cDepartment of Physics, Presidency College (Autonomous), Chennai 600 005, India
^*Correspondence e-mail: a_spandian@yahoo.com

(Received 16 April 2009; accepted 25 August 2009; online 5 September 2009)

In the title compound, C₂₉H₂₉ClN₂O₇, the isoxazole and dioxolane rings adopt envelope conformations, and the furan ring adopts a twisted conformation. The crystal structure is stabilized by intermolecular C—H⋯π interactions between a benzyloxy methylene H atom and the 4-chlorophenyl ring of an adjacent molecule, and by weak non-classical intermolecular C—H⋯O hydrogen bonds. In addition, the crystal structure exhibits a Cl⋯O halogen bond of 3.111 (3) Å, with a nearly linear C—Cl⋯O angle of 160.7 (1)°.

Related literature

For general background to 1,3-dipolar cycloaddition reactions, see: Gothelf & Jorgensen (1998 ); Bernotas et al. (1996 ); Breuer (1982 ); Colombi et al. (1978 ); Hossain et al. (1993 ). For ring puckering parameters, see: Cremer & Pople (1975 ); Nardelli (1983 ). For halogen bonds, see: Politzer et al. (2007 ).

Experimental

Crystal data

C₂₉H₂₉ClN₂O₇
M_r = 552.99
Orthorhombic, P 2₁ 2₁ 2₁
a = 12.7862 (5) Å
b = 13.0160 (5) Å
c = 16.8232 (6) Å
V = 2799.80 (18) Å³
Z = 4
Mo Kα radiation
μ = 0.19 mm⁻¹
T = 293 K
0.3 × 0.2 × 0.2 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker 2004 ) T_min = 0.926, T_max = 0.964
17056 measured reflections
4764 independent reflections
3446 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.037
wR(F²) = 0.088
S = 1.02
4764 reflections
355 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.14 e Å⁻³
Absolute structure: Flack (1983 ), 1975 Friedel pairs
Flack parameter: −0.05 (8)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C13—H13⋯O2ⁱ	0.98	2.54	3.298 (3)	134
C17—H17B⋯O1ⁱⁱ	0.97	2.46	3.218 (3)	135
C21—H21⋯Cg1ⁱ	0.93	2.75	3.598 (1)	152
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ . Cg1 is the centroid of the C1–C6 ring.

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 1998 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809034096/lx2103sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809034096/lx2103Isup2.hkl

checkCIF report

Comment top

The 1,3-dipolar cycloaddition of nitrones with olefinic dipolarophiles proceeds through a concerted mechanism yielding highly substituted isoxazolidines (Gothelf & Jorgensen, 1998). The cornerstone for cycloaddition reactions, nitrones, are excellent spin traping (Bernotas et al., 1996) and highly versatile synthetic intermediates (Breuer, 1982). Highly substituted spiro-isoxazolidines result from the 1,3-dipolar cycloaddition of exocylic olefins with nitrones and these spiro-isoxazolidines have also been transformed into complex heterocycles (Colombi et al., 1978, Hossain et al., 1993). Here we report the crystal structure of the title compound (Fig. 1).

The dihedral angle between the phenyl rings C1-C6 and C18-C23, C18-C23 and C24-C29, and, C1-C6 and C24-C29 are 8.4 (2), 83.9 (1) and 75.7 (1)°, respectively. The five membered tetrahydrofuran ring (C10-C13/O4) adopts a twisted conformation and the other five membered rings, isoxazole ring (C7-C9/O1/N1) and the dioxolan ring (C12-C14/O5/O6), adopt envelope conformations on C11 and C10, O1 and O5 with a pseudo-twofold axis passing through C12–C11, C9–C8 and C13–O6 bonds. The puckering parameters (Cremer & Pople, 1975) and the lowest displacement asymmetry parameters (Nardelli, 1983)as follows: for the tetrahydrofuran ring q₂ = 0.365 (1) Å, ϕ = 304.9 (1)°, Δ_S (C10) is 12.8 (1)° and Δ₂ (C13) is 1.8 (1)°, for the isoxazolidine ring q₂ = 0.377 (1) Å, ϕ = 359.7 (1)°, Δ_S (O1) is 1.0 (1)° and Δ₂(C8) is 19.6 (1)° and for the dioxolone ring q₂ = 0.248 (1) Å, ϕ = 181.2 (1)°, Δ_S (O5) is 0.3 (1)° and Δ₂ (C13) is 13.3 (1)°.

The molecular packing is stabilized by weak non-classical intermolecular C–H···O hydrogen bonds (Table 1 and Fig. 2; symmetry code as in Fig. 2). Additionally, the crystal structure exhibits a Cl···O halogen bond (Politzer et al., 2007) between the chlorine atom and the oxygen of a neighbouring NO₂ group, with a Cl1···O2^iv distance of 3.111 (3) Å (symmetry code as in Fig. 2). The molecular packing (Fig. 3) is further stabilized by an intermolecular C–H···π interactions between the methylene H atom of benzyloxy substituent and the 4-chlorophenyl ring of an adjacent molecule, with a C21–H21···Cg1ⁱⁱⁱ separation of 2.75 Å (Table 1, Cg1 is the centroid of C1-C6 benzene ring).

Related literature top

For general background to 1,3-dipolar cycloaddition reactions, see: Gothelf & Jorgensen (1998); Bernotas et al. (1996); Breuer (1982); Colombi et al. (1978); Hossain et al. (1993). For ring puckering parameters, see: Cremer & Pople (1975); Nardelli (1983). For halogen bonds, see: Politzer et al. (2007). Cg1 is the centroid of the C1–C6 ring.

Experimental top

A mixture of D-glucose derived nitrone (0.5 mmol) and β-nitrostyrene (0.5 mmol) was refluxed in dry toluene (10 ml) until completion of the reaction as evidenced by TLC analysis. The solvent was evaporated under reduced pressure. The crude was purified by column chromatography on silica gel (Merck, 100-200 mesh, ethylacetate-petroleum ether (10 : 90) to afford pure isoxazolidine. Single crystals of the title compound suitable for X-ray diffraction was recrystallized from ethanol.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of the title compound with the atom numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. The C–H···O interactions, and Cl1···O halogen bond (dashed lines) in the title compound. [Symmetry codes: (i) x - 1/2, -y + 1/2, -z + 1; (ii) - x + 1, y - 1/2, -z + 3/2; (iv) x - 1/2, - y + 3/2, -z + 1.]
	Fig. 3. C–H···π interactions (dashed lines) in the title compound. Cg denotes the ring centroid. [Symmetry codes: (iii) x + 1/2, - y + 1/2, - z + 1; (v) x - 1/2, - y + 1/2, - z + 1.]

3-(6-Benzyloxy-2,2-dimethylperhydrofuro[2,3-d][1,3]dioxolan-5-yl)- 5-(4-chlorophenyl)-4-nitro-2-phenyl-2,3,4,5-tetrahydroisoxazole top

Crystal data top

C₂₉H₂₉ClN₂O₇	F(000) = 1160
M_r = 552.99	D_x = 1.312 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 3652 reflections
a = 12.7862 (5) Å	θ = 2.5–25°
b = 13.0160 (5) Å	µ = 0.19 mm⁻¹
c = 16.8232 (6) Å	T = 293 K
V = 2799.80 (18) Å³	Needle, colourless
Z = 4	0.3 × 0.2 × 0.2 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	4764 independent reflections
Radiation source: fine-focus sealed tube	3446 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω and ϕ scans	θ_max = 25.0°, θ_min = 2.9°
Absorption correction: multi-scan (SADABS; Bruker 2004)	h = −15→15
T_min = 0.926, T_max = 0.964	k = −13→14
17056 measured reflections	l = −16→20

Refinement top

Refinement on F²	Hydrogen site location: difference Fourier map
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.037	w = 1/[σ²(F_o²) + (0.0403P)² + 0.2549P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.088	(Δ/σ)_max < 0.001
S = 1.02	Δρ_max = 0.15 e Å⁻³
4764 reflections	Δρ_min = −0.14 e Å⁻³
355 parameters	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
1 restraint	Extinction coefficient: 0.0045 (6)
Primary atom site location: structure-invariant direct methods	Absolute structure: Flack (1983), 1975 Friedel pairs
Secondary atom site location: difference Fourier map	Absolute structure parameter: −0.05 (8)

Crystal data top

C₂₉H₂₉ClN₂O₇	V = 2799.80 (18) Å³
M_r = 552.99	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 12.7862 (5) Å	µ = 0.19 mm⁻¹
b = 13.0160 (5) Å	T = 293 K
c = 16.8232 (6) Å	0.3 × 0.2 × 0.2 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	4764 independent reflections
Absorption correction: multi-scan (SADABS; Bruker 2004)	3446 reflections with I > 2σ(I)
T_min = 0.926, T_max = 0.964	R_int = 0.034
17056 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	H-atom parameters constrained
wR(F²) = 0.088	Δρ_max = 0.15 e Å⁻³
S = 1.02	Δρ_min = −0.14 e Å⁻³
4764 reflections	Absolute structure: Flack (1983), 1975 Friedel pairs
355 parameters	Absolute structure parameter: −0.05 (8)
1 restraint

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	0.33984 (19)	0.6866 (2)	0.65294 (16)	0.0602 (7)
H1	0.3415	0.6459	0.6983	0.072*
C2	0.2814 (2)	0.7761 (2)	0.65257 (18)	0.0692 (7)
H2	0.2457	0.7964	0.6981	0.083*
C3	0.2765 (2)	0.8340 (2)	0.5857 (2)	0.0673 (7)
C4	0.3326 (2)	0.8082 (2)	0.5200 (2)	0.0760 (9)
H4	0.3301	0.8493	0.4749	0.091*
C5	0.3933 (2)	0.7205 (2)	0.52082 (18)	0.0691 (8)
H5	0.4332	0.7039	0.4764	0.083*
C6	0.39575 (17)	0.65738 (18)	0.58632 (15)	0.0471 (6)
C7	0.45334 (17)	0.55719 (17)	0.58177 (14)	0.0455 (6)
H7	0.5181	0.5658	0.5513	0.055*
C8	0.38927 (17)	0.46762 (17)	0.54776 (13)	0.0427 (6)
H8	0.3143	0.4808	0.5544	0.051*
C9	0.42248 (17)	0.37460 (18)	0.59803 (14)	0.0434 (6)
H9	0.4536	0.3214	0.5643	0.052*
C10	0.33056 (15)	0.33112 (18)	0.64465 (14)	0.0434 (6)
H10	0.3092	0.3802	0.6857	0.052*
C11	0.34793 (16)	0.22621 (18)	0.68184 (14)	0.0448 (6)
H11	0.3831	0.2310	0.7335	0.054*
C12	0.23650 (18)	0.18767 (19)	0.68975 (14)	0.0474 (6)
H12	0.2314	0.1126	0.6886	0.057*
C13	0.17952 (16)	0.23875 (19)	0.62140 (14)	0.0460 (6)
H13	0.1606	0.1884	0.5805	0.055*
C14	0.08681 (19)	0.2635 (2)	0.73843 (15)	0.0582 (7)
C15	0.0626 (3)	0.3618 (3)	0.7812 (2)	0.1063 (12)
H15A	0.1132	0.4131	0.7668	0.159*
H15B	0.0653	0.3503	0.8375	0.159*
H15C	−0.0060	0.3849	0.7666	0.159*
C16	0.0104 (2)	0.1788 (3)	0.7552 (2)	0.0866 (10)
H16A	−0.0575	0.1981	0.7359	0.130*
H16B	0.0069	0.1669	0.8114	0.130*
H16C	0.0328	0.1171	0.7289	0.130*
C17	0.4468 (2)	0.0741 (2)	0.66159 (16)	0.0585 (7)
H17A	0.3903	0.0319	0.6819	0.070*
H17B	0.4917	0.0925	0.7058	0.070*
C18	0.50869 (17)	0.01390 (19)	0.60141 (15)	0.0493 (6)
C19	0.5602 (2)	−0.0733 (2)	0.62669 (19)	0.0713 (8)
H19	0.5570	−0.0928	0.6798	0.086*
C20	0.6160 (2)	−0.1312 (3)	0.5736 (2)	0.0875 (10)
H20	0.6507	−0.1899	0.5910	0.105*
C21	0.6215 (2)	−0.1038 (3)	0.4954 (2)	0.0811 (9)
H21	0.6591	−0.1439	0.4597	0.097*
C22	0.5717 (2)	−0.0176 (2)	0.46998 (17)	0.0713 (8)
H22	0.5757	0.0018	0.4169	0.086*
C23	0.5151 (2)	0.0412 (2)	0.52292 (16)	0.0608 (7)
H23	0.4809	0.1000	0.5052	0.073*
C24	0.60915 (17)	0.3964 (2)	0.63870 (14)	0.0489 (6)
C25	0.63995 (19)	0.2974 (2)	0.62056 (17)	0.0639 (8)
H25	0.5905	0.2457	0.6140	0.077*
C26	0.7453 (2)	0.2761 (3)	0.61224 (17)	0.0790 (9)
H26	0.7663	0.2100	0.5988	0.095*
C27	0.8194 (2)	0.3512 (3)	0.62345 (18)	0.0847 (11)
H27	0.8901	0.3359	0.6187	0.102*
C28	0.7876 (2)	0.4485 (3)	0.64162 (19)	0.0805 (10)
H28	0.8373	0.4999	0.6485	0.097*
C29	0.68311 (17)	0.4720 (2)	0.64995 (16)	0.0618 (7)
H29	0.6626	0.5384	0.6631	0.074*
N1	0.50029 (14)	0.41439 (15)	0.65469 (12)	0.0476 (5)
N2	0.4148 (2)	0.45251 (17)	0.46170 (13)	0.0574 (6)
O1	0.47679 (12)	0.52172 (12)	0.66073 (9)	0.0517 (4)
O2	0.4993 (2)	0.4215 (2)	0.44423 (13)	0.0993 (8)
O3	0.3483 (2)	0.4733 (2)	0.41370 (13)	0.1086 (8)
O4	0.24623 (11)	0.31531 (12)	0.59000 (9)	0.0503 (4)
O5	0.19043 (12)	0.23172 (14)	0.75864 (9)	0.0588 (5)
O6	0.08979 (12)	0.28308 (14)	0.65527 (10)	0.0613 (5)
O7	0.40491 (11)	0.16447 (12)	0.62710 (9)	0.0478 (4)
Cl1	0.19572 (8)	0.94167 (6)	0.58228 (7)	0.1059 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0647 (16)	0.0588 (18)	0.0572 (16)	0.0114 (14)	−0.0014 (14)	−0.0080 (14)
C2	0.0688 (17)	0.070 (2)	0.0692 (16)	0.0167 (16)	−0.0049 (15)	−0.0232 (13)
C3	0.0706 (18)	0.0432 (17)	0.0883 (19)	0.0018 (14)	−0.0139 (17)	−0.0167 (13)
C4	0.099 (2)	0.0429 (18)	0.086 (2)	−0.0020 (17)	−0.0028 (19)	0.0106 (16)
C5	0.088 (2)	0.0506 (18)	0.0687 (19)	−0.0036 (16)	0.0181 (16)	−0.0007 (15)
C6	0.0449 (13)	0.0404 (15)	0.0559 (15)	−0.0077 (11)	0.0023 (12)	−0.0126 (13)
C7	0.0447 (13)	0.0421 (15)	0.0497 (15)	−0.0055 (11)	0.0041 (11)	−0.0071 (12)
C8	0.0416 (12)	0.0425 (14)	0.0439 (14)	−0.0004 (11)	0.0024 (10)	−0.0035 (11)
C9	0.0385 (12)	0.0433 (15)	0.0485 (14)	0.0025 (10)	−0.0014 (11)	−0.0027 (12)
C10	0.0388 (12)	0.0432 (15)	0.0482 (14)	0.0006 (11)	−0.0034 (10)	−0.0004 (11)
C11	0.0452 (13)	0.0443 (15)	0.0450 (13)	0.0031 (11)	−0.0028 (11)	0.0019 (12)
C12	0.0530 (14)	0.0414 (15)	0.0479 (14)	0.0007 (12)	0.0052 (11)	0.0001 (12)
C13	0.0439 (12)	0.0471 (15)	0.0471 (13)	−0.0059 (12)	0.0000 (10)	−0.0003 (12)
C14	0.0540 (15)	0.0662 (19)	0.0544 (16)	0.0074 (14)	0.0049 (13)	−0.0018 (14)
C15	0.120 (3)	0.101 (3)	0.099 (3)	0.031 (2)	0.007 (2)	−0.033 (2)
C16	0.0640 (18)	0.104 (3)	0.091 (2)	−0.0119 (19)	0.0126 (16)	0.026 (2)
C17	0.0702 (17)	0.0496 (17)	0.0556 (16)	0.0215 (14)	−0.0020 (13)	0.0105 (13)
C18	0.0447 (13)	0.0441 (16)	0.0592 (17)	0.0053 (12)	0.0004 (11)	0.0064 (13)
C19	0.0730 (18)	0.065 (2)	0.076 (2)	0.0201 (17)	0.0068 (15)	0.0156 (16)
C20	0.078 (2)	0.069 (2)	0.115 (3)	0.0330 (17)	0.018 (2)	0.013 (2)
C21	0.0659 (19)	0.065 (2)	0.112 (3)	0.0099 (17)	0.0286 (18)	−0.014 (2)
C22	0.0799 (19)	0.069 (2)	0.0653 (19)	−0.0030 (18)	0.0187 (16)	−0.0046 (16)
C23	0.0703 (17)	0.0506 (17)	0.0615 (18)	0.0124 (14)	0.0001 (14)	0.0040 (14)
C24	0.0386 (13)	0.0631 (19)	0.0451 (15)	0.0009 (13)	−0.0026 (11)	0.0005 (12)
C25	0.0474 (14)	0.070 (2)	0.0742 (18)	0.0103 (14)	−0.0031 (13)	−0.0081 (15)
C26	0.0579 (17)	0.100 (3)	0.080 (2)	0.0289 (19)	0.0031 (15)	−0.0037 (19)
C27	0.0411 (16)	0.138 (3)	0.075 (2)	0.015 (2)	0.0063 (14)	0.023 (2)
C28	0.0423 (15)	0.117 (3)	0.082 (2)	−0.0142 (18)	−0.0024 (14)	0.024 (2)
C29	0.0479 (14)	0.0722 (19)	0.0652 (17)	−0.0065 (14)	−0.0031 (12)	0.0012 (15)
N1	0.0396 (11)	0.0478 (13)	0.0553 (12)	0.0014 (9)	−0.0010 (9)	−0.0058 (10)
N2	0.0776 (15)	0.0449 (13)	0.0497 (14)	−0.0107 (12)	−0.0008 (13)	−0.0059 (11)
O1	0.0526 (9)	0.0512 (11)	0.0513 (11)	0.0034 (8)	−0.0048 (7)	−0.0116 (9)
O2	0.1055 (18)	0.123 (2)	0.0690 (14)	0.0167 (16)	0.0285 (13)	−0.0203 (13)
O3	0.136 (2)	0.125 (2)	0.0645 (14)	0.0038 (17)	−0.0251 (14)	0.0137 (14)
O4	0.0404 (8)	0.0540 (11)	0.0565 (10)	−0.0071 (8)	−0.0082 (7)	0.0133 (8)
O5	0.0541 (10)	0.0757 (13)	0.0465 (10)	0.0024 (9)	0.0008 (8)	0.0010 (9)
O6	0.0485 (10)	0.0762 (13)	0.0591 (11)	0.0070 (9)	0.0053 (8)	0.0097 (10)
O7	0.0547 (9)	0.0422 (10)	0.0467 (9)	0.0116 (8)	−0.0005 (7)	0.0056 (8)
Cl1	0.1104 (7)	0.0618 (5)	0.1454 (9)	0.0290 (5)	−0.0323 (6)	−0.0224 (6)

Geometric parameters (Å, º) top

C1—C6	1.383 (3)	C15—H15A	0.9600
C1—C2	1.383 (4)	C15—H15B	0.9600
C1—H1	0.9300	C15—H15C	0.9600
C2—C3	1.355 (4)	C16—H16A	0.9600
C2—H2	0.9300	C16—H16B	0.9600
C3—C4	1.360 (4)	C16—H16C	0.9600
C3—Cl1	1.742 (3)	C17—O7	1.417 (3)
C4—C5	1.380 (4)	C17—C18	1.505 (3)
C4—H4	0.9300	C17—H17A	0.9700
C5—C6	1.375 (4)	C17—H17B	0.9700
C5—H5	0.9300	C18—C23	1.370 (3)
C6—C7	1.500 (3)	C18—C19	1.380 (3)
C7—O1	1.438 (3)	C19—C20	1.369 (4)
C7—C8	1.535 (3)	C19—H19	0.9300
C7—H7	0.9800	C20—C21	1.364 (5)
C8—N2	1.497 (3)	C20—H20	0.9300
C8—C9	1.537 (3)	C21—C22	1.360 (4)
C8—H8	0.9800	C21—H21	0.9300
C9—N1	1.472 (3)	C22—C23	1.380 (4)
C9—C10	1.522 (3)	C22—H22	0.9300
C9—H9	0.9800	C23—H23	0.9300
C10—O4	1.432 (3)	C24—C29	1.378 (3)
C10—C11	1.518 (3)	C24—C25	1.382 (4)
C10—H10	0.9800	C24—N1	1.437 (3)
C11—O7	1.423 (3)	C25—C26	1.382 (4)
C11—C12	1.516 (3)	C25—H25	0.9300
C11—H11	0.9800	C26—C27	1.374 (4)
C12—O5	1.421 (3)	C26—H26	0.9300
C12—C13	1.515 (3)	C27—C28	1.366 (5)
C12—H12	0.9800	C27—H27	0.9300
C13—O6	1.405 (3)	C28—C29	1.377 (4)
C13—O4	1.414 (3)	C28—H28	0.9300
C13—H13	0.9800	C29—H29	0.9300
C14—O6	1.423 (3)	N1—O1	1.433 (2)
C14—O5	1.429 (3)	N2—O2	1.191 (3)
C14—C15	1.500 (4)	N2—O3	1.203 (3)
C14—C16	1.500 (4)	Cl1—O2ⁱ	3.111 (3)

C6—C1—C2	120.5 (3)	C14—C15—H15A	109.5
C6—C1—H1	119.8	C14—C15—H15B	109.5
C2—C1—H1	119.8	H15A—C15—H15B	109.5
C3—C2—C1	119.8 (3)	C14—C15—H15C	109.5
C3—C2—H2	120.1	H15A—C15—H15C	109.5
C1—C2—H2	120.1	H15B—C15—H15C	109.5
C2—C3—C4	120.8 (3)	C14—C16—H16A	109.5
C2—C3—Cl1	120.2 (2)	C14—C16—H16B	109.5
C4—C3—Cl1	119.0 (3)	H16A—C16—H16B	109.5
C3—C4—C5	119.6 (3)	C14—C16—H16C	109.5
C3—C4—H4	120.2	H16A—C16—H16C	109.5
C5—C4—H4	120.2	H16B—C16—H16C	109.5
C6—C5—C4	121.0 (3)	O7—C17—C18	110.8 (2)
C6—C5—H5	119.5	O7—C17—H17A	109.5
C4—C5—H5	119.5	C18—C17—H17A	109.5
C5—C6—C1	118.3 (2)	O7—C17—H17B	109.5
C5—C6—C7	119.3 (2)	C18—C17—H17B	109.5
C1—C6—C7	122.3 (2)	H17A—C17—H17B	108.1
O1—C7—C6	109.53 (18)	C23—C18—C19	118.9 (2)
O1—C7—C8	102.22 (18)	C23—C18—C17	123.0 (2)
C6—C7—C8	114.67 (18)	C19—C18—C17	118.2 (2)
O1—C7—H7	110.0	C20—C19—C18	120.0 (3)
C6—C7—H7	110.0	C20—C19—H19	120.0
C8—C7—H7	110.0	C18—C19—H19	120.0
N2—C8—C7	110.11 (18)	C21—C20—C19	120.8 (3)
N2—C8—C9	111.63 (19)	C21—C20—H20	119.6
C7—C8—C9	104.23 (17)	C19—C20—H20	119.6
N2—C8—H8	110.2	C22—C21—C20	119.7 (3)
C7—C8—H8	110.2	C22—C21—H21	120.2
C9—C8—H8	110.2	C20—C21—H21	120.2
N1—C9—C10	108.61 (18)	C21—C22—C23	120.0 (3)
N1—C9—C8	105.42 (17)	C21—C22—H22	120.0
C10—C9—C8	111.29 (18)	C23—C22—H22	120.0
N1—C9—H9	110.5	C18—C23—C22	120.6 (3)
C10—C9—H9	110.5	C18—C23—H23	119.7
C8—C9—H9	110.5	C22—C23—H23	119.7
O4—C10—C11	104.21 (17)	C29—C24—C25	120.1 (2)
O4—C10—C9	107.70 (18)	C29—C24—N1	121.5 (2)
C11—C10—C9	115.70 (18)	C25—C24—N1	118.0 (2)
O4—C10—H10	109.7	C24—C25—C26	119.1 (3)
C11—C10—H10	109.7	C24—C25—H25	120.4
C9—C10—H10	109.7	C26—C25—H25	120.4
O7—C11—C12	110.55 (18)	C27—C26—C25	121.1 (3)
O7—C11—C10	108.43 (18)	C27—C26—H26	119.5
C12—C11—C10	101.32 (17)	C25—C26—H26	119.5
O7—C11—H11	112.0	C28—C27—C26	119.0 (3)
C12—C11—H11	112.0	C28—C27—H27	120.5
C10—C11—H11	112.0	C26—C27—H27	120.5
O5—C12—C13	104.04 (18)	C27—C28—C29	121.2 (3)
O5—C12—C11	109.12 (19)	C27—C28—H28	119.4
C13—C12—C11	103.89 (18)	C29—C28—H28	119.4
O5—C12—H12	113.0	C28—C29—C24	119.5 (3)
C13—C12—H12	113.0	C28—C29—H29	120.2
C11—C12—H12	113.0	C24—C29—H29	120.2
O6—C13—O4	110.77 (19)	O1—N1—C24	112.06 (18)
O6—C13—C12	105.37 (18)	O1—N1—C9	104.32 (16)
O4—C13—C12	107.62 (17)	C24—N1—C9	118.42 (18)
O6—C13—H13	111.0	O2—N2—O3	123.5 (3)
O4—C13—H13	111.0	O2—N2—C8	118.8 (2)
C12—C13—H13	111.0	O3—N2—C8	117.8 (2)
O6—C14—O5	105.13 (18)	N1—O1—C7	106.94 (16)
O6—C14—C15	108.9 (2)	C13—O4—C10	108.40 (16)
O5—C14—C15	108.9 (2)	C12—O5—C14	107.88 (17)
O6—C14—C16	109.5 (2)	C13—O6—C14	110.31 (18)
O5—C14—C16	110.3 (2)	C17—O7—C11	113.41 (18)
C15—C14—C16	113.8 (3)	C3—Cl1—O2ⁱ	160.74 (11)

C6—C1—C2—C3	1.9 (4)	C17—C18—C23—C22	−179.1 (3)
C1—C2—C3—C4	−3.4 (4)	C21—C22—C23—C18	0.3 (4)
C1—C2—C3—Cl1	175.3 (2)	C29—C24—C25—C26	−1.4 (4)
C2—C3—C4—C5	1.6 (4)	N1—C24—C25—C26	−174.0 (2)
Cl1—C3—C4—C5	−177.2 (2)	C24—C25—C26—C27	1.5 (4)
C3—C4—C5—C6	1.8 (4)	C25—C26—C27—C28	−1.2 (5)
C4—C5—C6—C1	−3.2 (4)	C26—C27—C28—C29	1.0 (5)
C4—C5—C6—C7	173.4 (2)	C27—C28—C29—C24	−0.9 (4)
C2—C1—C6—C5	1.4 (4)	C25—C24—C29—C28	1.1 (4)
C2—C1—C6—C7	−175.1 (2)	N1—C24—C29—C28	173.5 (2)
C5—C6—C7—O1	160.2 (2)	C29—C24—N1—O1	16.3 (3)
C1—C6—C7—O1	−23.3 (3)	C25—C24—N1—O1	−171.2 (2)
C5—C6—C7—C8	−85.6 (3)	C29—C24—N1—C9	137.8 (2)
C1—C6—C7—C8	90.9 (3)	C25—C24—N1—C9	−49.7 (3)
O1—C7—C8—N2	−143.01 (19)	C10—C9—N1—O1	−95.32 (19)
C6—C7—C8—N2	98.6 (2)	C8—C9—N1—O1	24.0 (2)
O1—C7—C8—C9	−23.2 (2)	C10—C9—N1—C24	139.3 (2)
C6—C7—C8—C9	−141.6 (2)	C8—C9—N1—C24	−101.3 (2)
N2—C8—C9—N1	118.5 (2)	C7—C8—N2—O2	68.6 (3)
C7—C8—C9—N1	−0.3 (2)	C9—C8—N2—O2	−46.6 (3)
N2—C8—C9—C10	−124.0 (2)	C7—C8—N2—O3	−110.8 (2)
C7—C8—C9—C10	117.22 (19)	C9—C8—N2—O3	133.9 (2)
N1—C9—C10—O4	166.62 (17)	C24—N1—O1—C7	88.2 (2)
C8—C9—C10—O4	51.0 (2)	C9—N1—O1—C7	−41.12 (19)
N1—C9—C10—C11	−77.3 (2)	C6—C7—O1—N1	161.96 (16)
C8—C9—C10—C11	167.08 (18)	C8—C7—O1—N1	39.96 (19)
O4—C10—C11—O7	78.2 (2)	O6—C13—O4—C10	101.9 (2)
C9—C10—C11—O7	−39.9 (2)	C12—C13—O4—C10	−12.8 (2)
O4—C10—C11—C12	−38.2 (2)	C11—C10—O4—C13	32.4 (2)
C9—C10—C11—C12	−156.24 (19)	C9—C10—O4—C13	155.77 (18)
O7—C11—C12—O5	164.63 (18)	C13—C12—O5—C14	26.3 (2)
C10—C11—C12—O5	−80.6 (2)	C11—C12—O5—C14	136.67 (19)
O7—C11—C12—C13	−84.9 (2)	O6—C14—O5—C12	−26.7 (3)
C10—C11—C12—C13	29.9 (2)	C15—C14—O5—C12	−143.2 (2)
O5—C12—C13—O6	−15.9 (2)	C16—C14—O5—C12	91.3 (2)
C11—C12—C13—O6	−130.13 (19)	O4—C13—O6—C14	−116.2 (2)
O5—C12—C13—O4	102.3 (2)	C12—C13—O6—C14	−0.1 (3)
C11—C12—C13—O4	−11.9 (2)	O5—C14—O6—C13	16.1 (3)
O7—C17—C18—C23	−4.6 (3)	C15—C14—O6—C13	132.6 (2)
O7—C17—C18—C19	176.1 (2)	C16—C14—O6—C13	−102.4 (2)
C23—C18—C19—C20	−0.3 (4)	C18—C17—O7—C11	−178.33 (18)
C17—C18—C19—C20	179.0 (3)	C12—C11—O7—C17	−83.7 (2)
C18—C19—C20—C21	−0.1 (5)	C10—C11—O7—C17	166.09 (18)
C19—C20—C21—C22	0.6 (5)	C2—C3—Cl1—O2ⁱ	−90.1 (5)
C20—C21—C22—C23	−0.7 (5)	C4—C3—Cl1—O2ⁱ	88.7 (5)
C19—C18—C23—C22	0.2 (4)

Symmetry code: (i) x−1/2, −y+3/2, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O2ⁱⁱ	0.98	2.54	3.298 (3)	134
C17—H17B···O1ⁱⁱⁱ	0.97	2.46	3.218 (3)	135
C21—H21···Cg1ⁱⁱ	0.93	2.75	3.598 (1)	152

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

Experimental details

Crystal data
Chemical formula	C₂₉H₂₉ClN₂O₇
M_r	552.99
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	293
a, b, c (Å)	12.7862 (5), 13.0160 (5), 16.8232 (6)
V (Å³)	2799.80 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.19
Crystal size (mm)	0.3 × 0.2 × 0.2

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker 2004)
T_min, T_max	0.926, 0.964
No. of measured, independent and observed [I > 2σ(I)] reflections	17056, 4764, 3446
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.088, 1.02
No. of reflections	4764
No. of parameters	355
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.14
Absolute structure	Flack (1983), 1975 Friedel pairs
Absolute structure parameter	−0.05 (8)

Computer programs: APEX2 (Bruker, 2004), APEX2 and SAINT (Bruker, 2004), SAINT and XPREP (Bruker, 2004), SHELXS97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13···O2ⁱ	0.98	2.54	3.298 (3)	133.7
C17—H17B···O1ⁱⁱ	0.97	2.46	3.218 (3)	134.8
C21—H21···Cg1ⁱ	0.93	2.75	3.598 (1)	152.0

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

Acknowledgements

MNM and ASP thank Dr J. Jothi Kumar, Principal of Presidency College (Autonomous), Chennai, India, for providing the computer and internet facilities. The authors thank Dr Babu Vargheese, SAIF, IIT, Madras, India, for his help with the X-ray data collection.

References

Bernotas, R. C., Adams, G. & Albert, C. A. (1996). Tetrahedron, 52, 6519–6526. CrossRef CAS Web of Science Google Scholar
Brandenburg, K. (1998). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Breuer, E. (1982). The Chemistry of Amino, Nitroso and Nitro Compounds and their Derivatives, Part I, edited by S. Patai, ch. 13. New York: Wiley Interscience. Google Scholar
Bruker (2004). APEX2, SAINT, XPREP and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Colombi, S., Vecchio, G., Gottarelli, G., Samori, B., Lanfredi, A. M. M. & Tiripicchio, A. (1978). Tetrahedron, 34, 2967–2976. CSD CrossRef CAS Web of Science Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
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Hossain, N., Papchikhin, A., Plavec, J. & Chattopadhyaya, J. (1993). Tetrahedron, 49, 10133–10156. CrossRef CAS Web of Science Google Scholar
Nardelli, M. (1983). Acta Cryst. C39, 1141–1142. CrossRef CAS Web of Science IUCr Journals Google Scholar
Politzer, P., Lane, P., Concha, M. C., Ma, Y. & Murray, J. S. (2007). J. Mol. Model. 13, 305–311. Web of Science CrossRef PubMed CAS Google Scholar
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Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 65| Part 10| October 2009| Pages o2305-o2306

doi:10.1107/S1600536809034096

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3-(6-Benz­yl­oxy-2,2-di­methyl­perhydro­furo[2,3-d][1,3]dioxolan-5-yl)-5-(4-chloro­phen­yl)-4-nitro-2-phenyl-2,3,4,5-tetra­hydro­isoxazole

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

3-(6-Benzyloxy-2,2-dimethylperhydrofuro[2,3-d][1,3]dioxolan-5-yl)-5-(4-chlorophenyl)-4-nitro-2-phenyl-2,3,4,5-tetrahydroisoxazole