3-tert-Butyl 5-methyl (2R,4S,5R)-2-(4-methoxyphenyl)-4-(3-nitrophenyl)-1,3-oxazolidine-3,5-dicarboxylate

Montiel-Smith, S.; Bernès, S.; Sandoval-Ramírez, J.; Meza-Reyes, S.; Dubois, J.

doi:10.1107/S160053681204192X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Pages o3146-o3147

doi:10.1107/S160053681204192X

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3-tert-Butyl 5-methyl (2R,4S,5R)-2-(4-methoxyphenyl)-4-(3-nitrophenyl)-1,3-oxazolidine-3,5-dicarboxylate

Sara Montiel-Smith,^a Sylvain Bernès,^b ^* Jesús Sandoval-Ramírez,^a Socorro Meza-Reyes ^a and Joëlle Dubois ^c

^aBenemérita Universidad Autónoma de Puebla, Facultad de Ciencias Químicas, Ciudad Universitaria, Puebla, Pue. 72570, Mexico, ^bUniversidad Autónoma de Nuevo León, UANL, Facultad de Ciencias Químicas, Av. Universidad S/N, Ciudad Universitaria, San Nicolás de los Garza, Nuevo León CP 66451, Mexico, and ^cInstitut de Chimie des Substances Naturelles, CNRS, Avenue de la Terrasse, 91190 Gif-sur-Yvette, France
^*Correspondence e-mail: sylvain_bernes@hotmail.com

(Received 18 September 2012; accepted 6 October 2012; online 20 October 2012)

The title molecule, C₂₃H₂₆N₂O₈, was synthesized in three steps starting from m-nitrocinnamic acid. The central oxazolidine ring adopts an almost perfect envelope conformation with the O atom as the flap [puckering parameter φ = 0.3 (6)°]. The dihedral angle formed by the benzene rings is 61.81 (9)°. In the crystal, molecules are connected into double chains parallel to [010] by C—H⋯O hydrogen bonds. The absolute configuration was assigned from the synthetic procedure.

Related literature

For the Sharpless asymmetric aminohydroxylation, see: Rudolph et al. (1996 ). For the synthesis of the phenylisoserine precursor of the title molecule, see: Montiel-Smith et al. (2002 ). For the stereocontrolled formation of the oxazolidine in the title molecule, see: Denis et al. (1994 ). For the structure of a related chiral N-Boc-protected oxazolidine, see: Tinant et al. (1996 ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₃H₂₆N₂O₈
M_r = 458.46
Monoclinic, P 2₁
a = 10.383 (1) Å
b = 6.0303 (6) Å
c = 18.7366 (17) Å
β = 95.591 (4)°
V = 1167.57 (19) Å³
Z = 2
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 298 K
0.60 × 0.16 × 0.16 mm

Data collection

Siemens P4 diffractometer
3169 measured reflections
2275 independent reflections
1628 reflections with I > 2σ(I)
R_int = 0.024
3 standard reflections every 97 reflections intensity decay: 0.5%

Refinement

R[F² > 2σ(F²)] = 0.039
wR(F²) = 0.095
S = 1.02
2275 reflections
304 parameters
1 restraint
H-atom parameters constrained
Δρ_max = 0.12 e Å⁻³
Δρ_min = −0.13 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O15ⁱ	0.98	2.50	3.400 (4)	153
C5—H5A⋯O28ⁱⁱ	0.98	2.59	3.387 (4)	138
C26—H26A⋯O1ⁱⁱⁱ	0.93	2.59	3.252 (4)	128
Symmetry codes: (i) x, y+1, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z]$ ; (iii) x, y-1, z.

Data collection: XSCANS (Siemens, 1996 ); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681204192X/rz5008sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681204192X/rz5008Isup2.hkl

Supporting information file. DOI: 10.1107/S160053681204192X/rz5008Isup3.cml

checkCIF report

Comment top

The title compound is related to a project about new synthetic routes to obtain isoserines (α-hydroxy-β-amino acids). The stereocontrol of the synthesis is a key point, since chiral isoserines are found in bioactive substances, as in the side chain of the emblematic anti-cancer agent Paclitaxel, initially marketed under the brand name Taxol. We focused our efforts toward the synthesis of (2R,3S)-N-Boc-β-phenylisoserines (Montiel-Smith et al., 2002). Starting from commercially available m-nitrocinnamic acid, which was esterified in a first step, we probed various conditions for an asymmetric aminohydroxylation (Rudolph et al., 1996), and the best results were obtained by using tert-butyl-N-chlorocarbamate as the nitrogen source, (DHQ)₂PHAL (hydroquinine 1,4-phthalazinediyl diether) as chiral ligand, and K₂OsO₂(OH)₄ as catalyst. The desired phenylisoserine was eventually obtained with 81% ee (see compound 2c in Montiel-Smith et al., 2002). The title compound resulted from the protection of the amine and hydroxyl groups, via the formation of an oxazolidine (Fig. 1).

The molecular structure (Fig. 2) allowed to check for the configuration of chiral atoms C2 and C3 in the precursor isoserine 3, confirming that the chiral inductor (DHQ)₂PHAL affords the (2R,3S) isomer predominantly, as expected. The deduced configuration of the third stereocenter in the oxazolidine I, 2R, also agrees with literature data for related reactions (Denis et al., 1994). The substituents in the oxazolidine skeleton are arranged in such a way that steric hindrance is avoided. The oxazolidine exhibits a conformation very close to the ideal envelope conformation on O1, the puckering parameters (Cremer & Pople, 1975) being ϕ = 0.3 (6)° and q₂ = 0.331 (3) Å. The ring conformation is related to the substituents distribution. For instance, the X-ray structure for another N-Boc protected oxazolidine with a different absolute configuration, (2R,4R,5S), showed a twisted oxazolidine ring (Tinant et al., 1996).

The crystal structure (Fig. 3) is dominated by the stacking of bulky Boc groups, which are oriented along [100], with the molecules linked into double chains parallel to [010] by C—H···O hydrogen bonds (Table 1).

Related literature top

For the Sharpless asymmetric aminohydroxylation, see: Rudolph et al. (1996). For the synthesis of the phenylisoserine precursor of the title molecule, see: Montiel-Smith et al. (2002). For the stereocontrolled formation of the oxazolidine in the title molecule, see: Denis et al. (1994). For the structure of a related chiral N-Boc-protected oxazolidine, see: Tinant et al. (1996). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

The synthesis starting from commercially available m-nitrocinnamic acid 1 is depicted in Fig. 1. The two steps preparation of the phenylisoserine 3 has been published (Montiel-Smith et al., 2002; see compound 2c therein). The enantiospecific aminohydroxylation reaction was carried out using ^tBuOCONHCl as nitrogen source, reagent previously prepared in situ by reacting ^tBuOCONH₂ and ^tBuOCl in a NaOH solution. The last step to afford the title compound is a protection of the amine and hydroxyl groups of 3, via the formation of an oxazolidine, carried out by reacting 3 with 1-(dimethoxymethyl)-4-methoxybenzene in presence of pyridinium p-toluenesulfonate, in refluxing toluene. The isolated compound I was crystallized from AcOEt/heptane.

Computing details top

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS (Siemens, 1996); data reduction: XSCANS (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The 3-steps synthesis of the title molecule, (I). i) SOCl₂, MeOH, reflux; ii) (DHQ)₂PHAL, n-PrOH/^tBuOCONHCl; K₂OsO₂(OH)₄, 0 °C; iii) p-MeOC₆H₄CH(OMe)₂, PPTS, toluene, 80 °C.
	Fig. 2. ORTEP-like view of the title molecule, showing 30% displacement ellipsoids for non-H atoms.
	Fig. 3. Part of the crystal structure of the title compound, viewed along the b axis. In four molecules, the Boc substituents are shown using a spacefill representation, in order to emphasize the stacking for these groups in the crystal.

3-tert-Butyl 5-methyl (2R,4S,5R)- 2-(4-methoxyphenyl)-4-(3-nitrophenyl)-1,3-oxazolidine-3,5-dicarboxylate top

Crystal data top

C₂₃H₂₆N₂O₈	F(000) = 484
M_r = 458.46	D_x = 1.304 Mg m⁻³
Monoclinic, P2₁	Melting point = 388–391 K
Hall symbol: P 2yb	Mo Kα radiation, λ = 0.71073 Å
a = 10.383 (1) Å	Cell parameters from 58 reflections
b = 6.0303 (6) Å	θ = 3.9–11.9°
c = 18.7366 (17) Å	µ = 0.10 mm⁻¹
β = 95.591 (4)°	T = 298 K
V = 1167.57 (19) Å³	Block, colourless
Z = 2	0.60 × 0.16 × 0.16 mm

Data collection top

Siemens P4 diffractometer	R_int = 0.024
Radiation source: fine-focus sealed tube	θ_max = 25.0°, θ_min = 2.0°
Graphite monochromator	h = −12→1
ω scans	k = −7→1
3169 measured reflections	l = −22→22
2275 independent reflections	3 standard reflections every 97 reflections
1628 reflections with I > 2σ(I)	intensity decay: 0.5%

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-atom parameters constrained
wR(F²) = 0.095	w = 1/[σ²(F_o²) + (0.0467P)²] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
2275 reflections	Δρ_max = 0.12 e Å⁻³
304 parameters	Δρ_min = −0.13 e Å⁻³
1 restraint	Extinction correction: SHELXL97, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 constraints	Extinction coefficient: 0.017 (3)
Primary atom site location: structure-invariant direct methods

Crystal data top

C₂₃H₂₆N₂O₈	V = 1167.57 (19) Å³
M_r = 458.46	Z = 2
Monoclinic, P2₁	Mo Kα radiation
a = 10.383 (1) Å	µ = 0.10 mm⁻¹
b = 6.0303 (6) Å	T = 298 K
c = 18.7366 (17) Å	0.60 × 0.16 × 0.16 mm
β = 95.591 (4)°

Data collection top

Siemens P4 diffractometer	R_int = 0.024
3169 measured reflections	3 standard reflections every 97 reflections
2275 independent reflections	intensity decay: 0.5%
1628 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.039	1 restraint
wR(F²) = 0.095	H-atom parameters constrained
S = 1.02	Δρ_max = 0.12 e Å⁻³
2275 reflections	Δρ_min = −0.13 e Å⁻³
304 parameters

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

	x	y	z	U_iso*/U_eq
O1	0.7821 (2)	0.5989 (4)	0.18897 (11)	0.0582 (7)
C2	0.8184 (3)	0.5427 (6)	0.26275 (16)	0.0467 (8)
H2A	0.7769	0.6446	0.2942	0.056*
N3	0.7630 (3)	0.3207 (5)	0.26723 (13)	0.0474 (7)
C4	0.7412 (3)	0.2150 (6)	0.19661 (14)	0.0457 (8)
H4A	0.7970	0.0844	0.1947	0.055*
C5	0.7866 (3)	0.3983 (7)	0.14856 (17)	0.0543 (9)
H5A	0.7241	0.4104	0.1061	0.065*
C6	0.9643 (3)	0.5490 (5)	0.28030 (15)	0.0440 (8)
C7	1.0343 (3)	0.3772 (6)	0.31379 (17)	0.0508 (9)
H7A	0.9914	0.2492	0.3258	0.061*
C8	1.1675 (3)	0.3915 (7)	0.32989 (17)	0.0549 (9)
H8A	1.2129	0.2732	0.3520	0.066*
C9	1.2322 (3)	0.5807 (7)	0.31311 (16)	0.0519 (9)
C10	1.1655 (4)	0.7536 (7)	0.27930 (19)	0.0628 (10)
H10A	1.2090	0.8805	0.2668	0.075*
C11	1.0321 (4)	0.7370 (6)	0.26391 (19)	0.0603 (10)
H11A	0.9870	0.8558	0.2419	0.072*
O12	1.3643 (2)	0.5782 (5)	0.33188 (12)	0.0708 (8)
C13	1.4373 (4)	0.7685 (8)	0.3159 (2)	0.0840 (14)
H13A	1.5271	0.7437	0.3311	0.126*
H13B	1.4071	0.8949	0.3406	0.126*
H13C	1.4269	0.7953	0.2651	0.126*
C14	0.7368 (3)	0.2149 (6)	0.32801 (17)	0.0446 (8)
O15	0.7056 (2)	0.0214 (4)	0.32967 (12)	0.0564 (6)
O16	0.7505 (2)	0.3553 (4)	0.38389 (10)	0.0502 (6)
C17	0.7426 (3)	0.2749 (6)	0.45810 (16)	0.0556 (10)
C18	0.7608 (4)	0.4849 (8)	0.5014 (2)	0.0852 (14)
H18A	0.6974	0.5923	0.4834	0.128*
H18B	0.8460	0.5428	0.4975	0.128*
H18C	0.7506	0.4536	0.5507	0.128*
C19	0.6121 (4)	0.1736 (10)	0.4654 (2)	0.0896 (16)
H19A	0.5457	0.2681	0.4428	0.134*
H19B	0.6000	0.1575	0.5152	0.134*
H19C	0.6072	0.0307	0.4427	0.134*
C20	0.8534 (4)	0.1162 (10)	0.4763 (2)	0.0901 (14)
H20A	0.8410	−0.0143	0.4471	0.135*
H20B	0.8566	0.0757	0.5260	0.135*
H20C	0.9333	0.1864	0.4674	0.135*
C21	0.6011 (3)	0.1515 (6)	0.17565 (15)	0.0439 (8)
C22	0.4983 (3)	0.2716 (7)	0.19742 (18)	0.0613 (10)
H22A	0.5140	0.3881	0.2296	0.074*
C23	0.3719 (3)	0.2199 (8)	0.17162 (19)	0.0719 (12)
H23A	0.3036	0.3021	0.1866	0.086*
C24	0.3470 (3)	0.0468 (8)	0.12382 (18)	0.0637 (11)
H24A	0.2627	0.0117	0.1060	0.076*
C25	0.4499 (3)	−0.0711 (7)	0.10355 (15)	0.0494 (9)
C26	0.5756 (3)	−0.0233 (6)	0.12914 (15)	0.0465 (9)
H26A	0.6432	−0.1089	0.1150	0.056*
N27	0.4263 (3)	−0.2579 (6)	0.05319 (14)	0.0626 (9)
O28	0.3196 (3)	−0.2710 (6)	0.01928 (13)	0.0901 (11)
O29	0.5151 (3)	−0.3873 (6)	0.04674 (14)	0.0893 (9)
C30	0.9204 (4)	0.3588 (8)	0.12370 (18)	0.0605 (11)
O31	0.9865 (3)	0.1999 (6)	0.13651 (16)	0.0899 (10)
O32	0.9520 (3)	0.5284 (7)	0.08509 (16)	0.1015 (11)
C33	1.0810 (4)	0.5279 (14)	0.0607 (3)	0.137 (3)
H33A	1.0921	0.6582	0.0326	0.206*
H33B	1.0913	0.3983	0.0321	0.206*
H33C	1.1446	0.5267	0.1015	0.206*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0616 (14)	0.0538 (16)	0.0564 (13)	−0.0020 (14)	−0.0088 (11)	0.0128 (14)
C2	0.0548 (19)	0.042 (2)	0.0421 (17)	−0.0031 (18)	−0.0010 (14)	0.0022 (17)
N3	0.0571 (17)	0.0470 (17)	0.0376 (14)	−0.0109 (15)	0.0019 (12)	0.0019 (14)
C4	0.0458 (18)	0.052 (2)	0.0385 (16)	−0.0010 (18)	−0.0007 (13)	−0.0027 (17)
C5	0.054 (2)	0.063 (3)	0.0437 (17)	−0.008 (2)	−0.0041 (15)	0.005 (2)
C6	0.0543 (18)	0.036 (2)	0.0411 (16)	−0.0041 (18)	0.0005 (15)	0.0003 (16)
C7	0.053 (2)	0.046 (2)	0.0542 (19)	−0.0040 (19)	0.0073 (16)	0.0064 (18)
C8	0.057 (2)	0.054 (2)	0.054 (2)	0.004 (2)	0.0032 (16)	0.0095 (19)
C9	0.051 (2)	0.066 (3)	0.0385 (16)	−0.007 (2)	0.0045 (15)	−0.0062 (19)
C10	0.067 (2)	0.051 (2)	0.069 (2)	−0.016 (2)	0.0007 (18)	0.006 (2)
C11	0.063 (2)	0.042 (2)	0.073 (2)	−0.004 (2)	−0.0075 (18)	0.005 (2)
O12	0.0519 (15)	0.085 (2)	0.0746 (15)	−0.0143 (17)	0.0006 (12)	0.0006 (17)
C13	0.062 (2)	0.091 (4)	0.100 (3)	−0.033 (3)	0.014 (2)	−0.018 (3)
C14	0.0409 (18)	0.047 (2)	0.045 (2)	−0.0020 (19)	0.0015 (14)	−0.0019 (19)
O15	0.0693 (15)	0.0461 (16)	0.0547 (14)	−0.0124 (14)	0.0099 (11)	−0.0018 (12)
O16	0.0613 (14)	0.0495 (14)	0.0393 (11)	−0.0080 (13)	0.0026 (10)	−0.0022 (11)
C17	0.065 (2)	0.064 (3)	0.0383 (17)	−0.011 (2)	0.0088 (16)	0.0024 (19)
C18	0.108 (3)	0.092 (4)	0.055 (2)	−0.026 (3)	0.006 (2)	−0.017 (2)
C19	0.091 (3)	0.113 (4)	0.071 (2)	−0.035 (3)	0.038 (2)	−0.016 (3)
C20	0.104 (3)	0.103 (4)	0.061 (2)	0.011 (3)	−0.006 (2)	0.022 (3)
C21	0.0427 (18)	0.049 (2)	0.0398 (15)	−0.0022 (17)	0.0029 (14)	0.0001 (17)
C22	0.055 (2)	0.070 (3)	0.059 (2)	0.005 (2)	0.0047 (17)	−0.012 (2)
C23	0.049 (2)	0.096 (3)	0.072 (2)	0.014 (2)	0.0076 (18)	−0.011 (3)
C24	0.045 (2)	0.096 (3)	0.0491 (18)	−0.007 (2)	0.0001 (16)	−0.004 (2)
C25	0.052 (2)	0.063 (2)	0.0326 (15)	−0.0074 (19)	0.0009 (14)	−0.0010 (17)
C26	0.047 (2)	0.054 (2)	0.0382 (16)	−0.0030 (17)	0.0044 (14)	0.0000 (17)
N27	0.068 (2)	0.080 (3)	0.0386 (15)	−0.023 (2)	−0.0005 (15)	−0.0020 (18)
O28	0.0673 (17)	0.139 (3)	0.0621 (15)	−0.040 (2)	−0.0047 (13)	−0.0214 (19)
O29	0.105 (2)	0.087 (2)	0.0720 (17)	0.006 (2)	−0.0127 (16)	−0.0255 (19)
C30	0.061 (3)	0.077 (3)	0.0432 (19)	−0.016 (3)	0.0004 (17)	0.007 (2)
O31	0.079 (2)	0.099 (3)	0.098 (2)	0.005 (2)	0.0398 (16)	0.007 (2)
O32	0.0703 (18)	0.138 (3)	0.0973 (19)	−0.023 (2)	0.0104 (15)	0.049 (2)
C33	0.066 (3)	0.223 (8)	0.127 (4)	−0.030 (4)	0.031 (3)	0.062 (5)

Geometric parameters (Å, º) top

O1—C5	1.430 (4)	C17—C18	1.506 (5)
O1—C2	1.437 (4)	C17—C20	1.510 (6)
C2—N3	1.462 (5)	C18—H18A	0.9600
C2—C6	1.519 (4)	C18—H18B	0.9600
C2—H2A	0.9800	C18—H18C	0.9600
N3—C14	1.356 (4)	C19—H19A	0.9600
N3—C4	1.466 (4)	C19—H19B	0.9600
C4—C21	1.518 (4)	C19—H19C	0.9600
C4—C5	1.529 (5)	C20—H20A	0.9600
C4—H4A	0.9800	C20—H20B	0.9600
C5—C30	1.526 (5)	C20—H20C	0.9600
C5—H5A	0.9800	C21—C26	1.377 (4)
C6—C7	1.381 (4)	C21—C22	1.384 (5)
C6—C11	1.385 (5)	C22—C23	1.390 (5)
C7—C8	1.389 (5)	C22—H22A	0.9300
C7—H7A	0.9300	C23—C24	1.383 (6)
C8—C9	1.376 (5)	C23—H23A	0.9300
C8—H8A	0.9300	C24—C25	1.368 (5)
C9—C10	1.372 (5)	C24—H24A	0.9300
C9—O12	1.383 (4)	C25—C26	1.376 (4)
C10—C11	1.391 (5)	C25—N27	1.474 (5)
C10—H10A	0.9300	C26—H26A	0.9300
C11—H11A	0.9300	N27—O29	1.223 (4)
O12—C13	1.423 (5)	N27—O28	1.224 (4)
C13—H13A	0.9600	C30—O31	1.189 (5)
C13—H13B	0.9600	C30—O32	1.313 (5)
C13—H13C	0.9600	O32—C33	1.456 (5)
C14—O15	1.212 (4)	C33—H33A	0.9600
C14—O16	1.343 (4)	C33—H33B	0.9600
O16—C17	1.483 (4)	C33—H33C	0.9600
C17—C19	1.504 (5)

C5—O1—C2	106.9 (2)	C19—C17—C18	111.1 (3)
O1—C2—N3	101.7 (2)	O16—C17—C20	107.9 (3)
O1—C2—C6	111.4 (2)	C19—C17—C20	113.3 (4)
N3—C2—C6	113.6 (3)	C18—C17—C20	111.0 (3)
O1—C2—H2A	110.0	C17—C18—H18A	109.5
N3—C2—H2A	110.0	C17—C18—H18B	109.5
C6—C2—H2A	110.0	H18A—C18—H18B	109.5
C14—N3—C2	126.3 (3)	C17—C18—H18C	109.5
C14—N3—C4	121.8 (3)	H18A—C18—H18C	109.5
C2—N3—C4	111.9 (3)	H18B—C18—H18C	109.5
N3—C4—C21	113.8 (2)	C17—C19—H19A	109.5
N3—C4—C5	100.8 (3)	C17—C19—H19B	109.5
C21—C4—C5	111.9 (2)	H19A—C19—H19B	109.5
N3—C4—H4A	110.0	C17—C19—H19C	109.5
C21—C4—H4A	110.0	H19A—C19—H19C	109.5
C5—C4—H4A	110.0	H19B—C19—H19C	109.5
O1—C5—C30	111.8 (3)	C17—C20—H20A	109.5
O1—C5—C4	105.8 (2)	C17—C20—H20B	109.5
C30—C5—C4	114.1 (3)	H20A—C20—H20B	109.5
O1—C5—H5A	108.3	C17—C20—H20C	109.5
C30—C5—H5A	108.3	H20A—C20—H20C	109.5
C4—C5—H5A	108.3	H20B—C20—H20C	109.5
C7—C6—C11	117.3 (3)	C26—C21—C22	118.7 (3)
C7—C6—C2	123.3 (3)	C26—C21—C4	118.5 (3)
C11—C6—C2	119.4 (3)	C22—C21—C4	122.6 (3)
C6—C7—C8	121.4 (3)	C21—C22—C23	120.6 (4)
C6—C7—H7A	119.3	C21—C22—H22A	119.7
C8—C7—H7A	119.3	C23—C22—H22A	119.7
C9—C8—C7	120.0 (3)	C24—C23—C22	120.4 (4)
C9—C8—H8A	120.0	C24—C23—H23A	119.8
C7—C8—H8A	120.0	C22—C23—H23A	119.8
C10—C9—C8	120.0 (3)	C25—C24—C23	118.0 (3)
C10—C9—O12	124.7 (4)	C25—C24—H24A	121.0
C8—C9—O12	115.3 (4)	C23—C24—H24A	121.0
C9—C10—C11	119.2 (4)	C24—C25—C26	122.3 (3)
C9—C10—H10A	120.4	C24—C25—N27	119.2 (3)
C11—C10—H10A	120.4	C26—C25—N27	118.5 (3)
C6—C11—C10	122.0 (4)	C25—C26—C21	119.9 (3)
C6—C11—H11A	119.0	C25—C26—H26A	120.0
C10—C11—H11A	119.0	C21—C26—H26A	120.0
C9—O12—C13	118.2 (3)	O29—N27—O28	124.0 (4)
O12—C13—H13A	109.5	O29—N27—C25	118.1 (3)
O12—C13—H13B	109.5	O28—N27—C25	117.9 (4)
H13A—C13—H13B	109.5	O31—C30—O32	124.7 (4)
O12—C13—H13C	109.5	O31—C30—C5	126.1 (4)
H13A—C13—H13C	109.5	O32—C30—C5	109.3 (4)
H13B—C13—H13C	109.5	C30—O32—C33	117.2 (5)
O15—C14—O16	126.5 (3)	O32—C33—H33A	109.5
O15—C14—N3	123.4 (3)	O32—C33—H33B	109.5
O16—C14—N3	110.0 (3)	H33A—C33—H33B	109.5
C14—O16—C17	120.9 (3)	O32—C33—H33C	109.5
O16—C17—C19	110.5 (3)	H33A—C33—H33C	109.5
O16—C17—C18	102.4 (3)	H33B—C33—H33C	109.5

C5—O1—C2—N3	−34.8 (3)	C4—N3—C14—O15	7.2 (5)
C5—O1—C2—C6	86.6 (3)	C2—N3—C14—O16	9.3 (4)
O1—C2—N3—C14	−160.3 (3)	C4—N3—C14—O16	−172.8 (3)
C6—C2—N3—C14	80.0 (4)	O15—C14—O16—C17	7.2 (5)
O1—C2—N3—C4	21.7 (3)	N3—C14—O16—C17	−172.8 (2)
C6—C2—N3—C4	−98.1 (3)	C14—O16—C17—C19	−60.6 (4)
C14—N3—C4—C21	60.8 (4)	C14—O16—C17—C18	−179.0 (3)
C2—N3—C4—C21	−121.0 (3)	C14—O16—C17—C20	63.8 (4)
C14—N3—C4—C5	−179.3 (3)	N3—C4—C21—C26	−152.8 (3)
C2—N3—C4—C5	−1.1 (3)	C5—C4—C21—C26	93.8 (4)
C2—O1—C5—C30	−89.2 (3)	N3—C4—C21—C22	31.9 (4)
C2—O1—C5—C4	35.6 (3)	C5—C4—C21—C22	−81.6 (4)
N3—C4—C5—O1	−20.3 (3)	C26—C21—C22—C23	−1.4 (5)
C21—C4—C5—O1	100.9 (3)	C4—C21—C22—C23	174.0 (3)
N3—C4—C5—C30	103.0 (3)	C21—C22—C23—C24	0.1 (6)
C21—C4—C5—C30	−135.8 (3)	C22—C23—C24—C25	0.5 (6)
O1—C2—C6—C7	−129.1 (3)	C23—C24—C25—C26	0.1 (5)
N3—C2—C6—C7	−15.0 (4)	C23—C24—C25—N27	179.4 (3)
O1—C2—C6—C11	52.5 (4)	C24—C25—C26—C21	−1.4 (5)
N3—C2—C6—C11	166.7 (3)	N27—C25—C26—C21	179.3 (3)
C11—C6—C7—C8	−0.5 (5)	C22—C21—C26—C25	2.0 (4)
C2—C6—C7—C8	−178.9 (3)	C4—C21—C26—C25	−173.6 (3)
C6—C7—C8—C9	0.7 (5)	C24—C25—N27—O29	−165.8 (3)
C7—C8—C9—C10	−1.2 (5)	C26—C25—N27—O29	13.5 (5)
C7—C8—C9—O12	179.6 (3)	C24—C25—N27—O28	15.7 (5)
C8—C9—C10—C11	1.5 (5)	C26—C25—N27—O28	−164.9 (3)
O12—C9—C10—C11	−179.3 (3)	O1—C5—C30—O31	122.5 (4)
C7—C6—C11—C10	0.9 (5)	C4—C5—C30—O31	2.5 (5)
C2—C6—C11—C10	179.3 (3)	O1—C5—C30—O32	−57.8 (4)
C9—C10—C11—C6	−1.4 (5)	C4—C5—C30—O32	−177.8 (3)
C10—C9—O12—C13	0.6 (5)	O31—C30—O32—C33	−4.6 (6)
C8—C9—O12—C13	179.8 (3)	C5—C30—O32—C33	175.7 (4)
C2—N3—C14—O15	−170.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O15ⁱ	0.98	2.50	3.400 (4)	153
C5—H5A···O28ⁱⁱ	0.98	2.59	3.387 (4)	138
C26—H26A···O1ⁱⁱⁱ	0.93	2.59	3.252 (4)	128

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

Experimental details

Crystal data
Chemical formula	C₂₃H₂₆N₂O₈
M_r	458.46
Crystal system, space group	Monoclinic, P2₁
Temperature (K)	298
a, b, c (Å)	10.383 (1), 6.0303 (6), 18.7366 (17)
β (°)	95.591 (4)
V (Å³)	1167.57 (19)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.60 × 0.16 × 0.16

Data collection
Diffractometer	Siemens P4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3169, 2275, 1628
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.594

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.095, 1.02
No. of reflections	2275
No. of parameters	304
No. of restraints	1
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.12, −0.13

Computer programs: XSCANS (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O15ⁱ	0.98	2.50	3.400 (4)	153
C5—H5A···O28ⁱⁱ	0.98	2.59	3.387 (4)	138
C26—H26A···O1ⁱⁱⁱ	0.93	2.59	3.252 (4)	128

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

Acknowledgements

This work was supported by the France–Mexico ECOS-ANUIES (M97–E02) agreement.

References

Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Denis, J.-N., Kanazawa, A. M. & Green, A. E. (1994). Tetrahedron Lett. 35, 105–108. CrossRef CAS Web of Science Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Montiel-Smith, S., Cervantes-Mejía, V., Dubois, J., Guénard, D., Guéritte, F. & Sandoval-Ramírez, J. (2002). Eur. J. Org. Chem. pp. 2260–2264. Google Scholar
Rudolph, J., Sennhenn, P. C., Vlaar, C. P. & Sharpless, K. B. (1996). Angew. Chem. Int. Ed. 35, 2810–2813. CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Siemens (1996). XSCANS. Siemens Analytical X-ray Instruments Inc., Madison, Wisconsin, USA. Google Scholar
Tinant, B., Declercq, J. P. & Cagnon, J. R. (1996). Bull. Soc. Chim. Belg. 105, 325–328. CAS Google Scholar

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Volume 68| Part 11| November 2012| Pages o3146-o3147

doi:10.1107/S160053681204192X

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

3-tert-Butyl 5-methyl (2R,4S,5R)-2-(4-methoxyphenyl)-4-(3-nitro­phenyl)-1,3-oxazolidine-3,5-di­carboxylate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

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References

organic compounds

3-tert-Butyl 5-methyl (2R,4S,5R)-2-(4-methoxyphenyl)-4-(3-nitrophenyl)-1,3-oxazolidine-3,5-dicarboxylate