(5R)-3-(2-Chloro­acet­yl)-4-methyl-5-phenyl-1,3,4-oxadiazinan-2-one

Caracelli, I.; Coelho, D.C.S.; Olivato, P.R.; Rodrigues, A.; Tiekink, E.R.T.

doi:10.1107/S1600536811020356

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 7| July 2011| Pages o1571-o1572

doi:10.1107/S1600536811020356

Open

access

(5R)-3-(2-Chloroacetyl)-4-methyl-5-phenyl-1,3,4-oxadiazinan-2-one

Ignez Caracelli,^a ^* Daniel C. S. Coelho,^b Paulo R. Olivato,^c Alessandro Rodrigues ^d and Edward R. T. Tiekink ^e

^aBioMat-Departamento de Física, Universidade Federal de São Carlos, CP 676, 13565-905 São Carlos, SP, Brazil, ^bLaboratório de Cristalografia, Estereodinâmica e Modelagem Molecular, Universidade Federal de São Carlos, Departamento de Quïmica, CP 676, 13565-905 São Carlos, SP, Brazil, ^cUniversidade de São Paulo, Conformational Analysis and Electronic Interactions Laboratory, Instituto de Química, São Paulo, SP, Brazil, ^dDepartamento de Ciências Exatas e da Terra, Universidade Federal de São Paulo, UNIFESP, Diadema, Brazil, and ^eDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: ignez@ufscar.br

(Received 25 May 2011; accepted 27 May 2011; online 4 June 2011)

The 1,3,4-oxadiazinan-2-one ring in the title compound, C₁₂H₁₃ClN₂O₃, is in a distorted half-chair conformation. The phenyl and chloroacetyl groups occupy axial and equatorial positions, respectively, and lie to the opposite side of the molecule to the N-bound methyl substituent. Molecules are consolidated in the crystal structure by C—H⋯O interactions.

Related literature

For background to 1,3,4-oxadiazin-2-ones, see: Trepanier et al. (1968 ); Roussi et al. (1998 , 1999 , 2000 ); Casper et al. (2002a ,b ); Bonin et al. (2006 ). For a related structure, see: Zukerman-Schpector et al. (2009 ). For the synthesis, see: Rodrigues et al. (2005 ). For conformational analysis, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₁₂H₁₃ClN₂O₃
M_r = 268.69
Orthorhombic, P 2₁ 2₁ 2₁
a = 9.4862 (2) Å
b = 9.6237 (2) Å
c = 13.2433 (3) Å
V = 1209.01 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.32 mm⁻¹
T = 100 K
0.35 × 0.30 × 0.25 mm

Data collection

Bruker APEXII CCD diffractometer
29813 measured reflections
2378 independent reflections
2334 reflections with I > 2σ(I)
R_int = 0.026

Refinement

R[F² > 2σ(F²)] = 0.020
wR(F²) = 0.054
S = 1.07
2378 reflections
164 parameters
H-atom parameters constrained
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.20 e Å⁻³
Absolute structure: Flack (1983 ), 993 Friedel pairs
Flack parameter: 0.01 (5)

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯O3ⁱ	1.00	2.60	3.5142 (15)	153
C8—H8⋯O2ⁱⁱ	0.95	2.60	3.2689 (16)	128
C11—H11b⋯O2ⁱⁱⁱ	0.99	2.54	3.3675 (16)	141
C12—H12a⋯O2ⁱⁱⁱ	0.98	2.57	3.5448 (16)	173
Symmetry codes: (i) $[-x+{\script{1\over 2}}, -y, z-{\script{1\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+2]$ ; (iii) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and DIAMOND (Brandenburg, 2006 ); software used to prepare material for publication: MarvinSketch (Chemaxon, 2010 ) and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811020356/hg5045sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811020356/hg5045Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811020356/hg5045Isup3.cml

checkCIF report

Comment top

About forty years ago Trepanier and collaborators reported the first synthesis of some 3,4,5,6-tetrahydro-2H-1,3,4-oxadiazin-2-ones as candidates for central nervous system stimulant activity (Trepanier et al., 1968). After three decades from the discovery of 1,3,4-oxadiazin-2-ones, Husson, Micouin and co-workers (Roussi et al., 1998) successfully employed this class of compound as chiral auxiliaries in diastereoselective alkylations and in dipolar cycloadditions (Roussi et al., 1999, 2000, Bonin et al., 2006). In a different approach, Hitchcock and collaborators have been successfully applying 1,3,4-oxadiazinan-2-one derivatives as chiral auxiliaries in asymmetric aldol addition reactions (Casper et al., 2002b). Besides their applications in asymmetric synthesis, this class of compounds show a very interesting conformational behaviour (Casper et al., 2002a). To explore the adopted conformation of the title compound, (I), in the solid-state, an X-ray study was performed.

The crystal structure analysis of (I) confirms the R configuration at atom C2, Fig. 1, in accord with expectation from the synthesis. The 1,3,4-oxadiazinan-2-one ring is in a distorted half-chair conformation, as shown by the ring-puckering parameters: q₂ = 0.364 (1) Å, q₃ = -0.333 (1) Å, Q = 493 (1) Å and ϕ₂ = 32.0 (2) ° (Cremer and Pople, 1975). The deviations of the O1, C1, N1, N2, C2 and C3 atoms from their least-squares plane are 0.0424 (10) -0.0497 (13), -0.1285 (11), 0.3139 (11), -0.3212 (13) and 0.1430 (13) Å, respectively. The observed conformation contrasts the twisted chair conformation found in the only other single-ring 1,3,4-oxadiazinan-2-one structure known (Zukerman-Schpector et al., 2009). The chloridoacetyl and phenyl groups lie to the same side of the molecule and opposite to that of the N-bound methyl group. The dihedral angles formed between the 1,3,4-oxadiazinan-2-one ring and the phenyl and chloridoacetyl (Cl,O3,C10,C11) groups are 87.69 (6) and 14.41 (3) °, respectively, consistent with axial and equatorial substitution. Molecules are consolidated in the crystal packing by C—H···O interactions operating in three-dimensions, Table 1 and Fig. 2.

Related literature top

For background to 1,3,4-oxadiazin-2-ones, see: Trepanier et al. (1968); Roussi et al. (1998, 1999, 2000); Casper et al. (2002a,b); Bonin et al. (2006). For a related structure, see: Zukerman-Schpector et al. (2009). For the synthesis, see: Rodrigues et al. (2005). For conformational analysis, see: Cremer & Pople (1975).

Experimental top

The starting (R)-4-methyl-5-phenyl-1,3,4-oxadiazinan-2-one was synthesized by using the same procedure as previously reported (Rodrigues et al. 2005). The chlorooacetyl-1,3,4-oxadiazinan-2-one (I) species was prepared by the acylation reaction of 1,3,4-oxadiazinan-2-one. A solution of BuLi (2.00 M in hexane, 1.45 ml, 2.86 mmol) was added drop wise to a solution of 1,3,4-oxadiazinan-2-one (500 mg, 2.60 mmol) in dry THF (10 ml) at 195 K and the reaction was stirred for an additional 15 min. A chloroacetyl chloride (230 µL, 2.86 mmol) solution in THF (1 ml) was added slowly to the reaction mixture. After 15 min, the light-yellow solution was warmed to RT for a further 30 min. The reaction was quenched with saturated aqueous ammonium chloride solution (5 ml). The mixture was concentrated under reduced pressure, taken up in water (5 ml) and extracted with DCM (3 times; 15 ml) then dried (MgSO₄). Evaporation of the solvent in vacuo gave the crude product which was purified by flash column chromatography on silica gel with 40% EtOAc in hexanes to give the pure product as a colourless solid (572 mg, 82%). Colourless crystals of (I) were obtained by vapour diffusion from hexane/acetone at 298 K. mp = 408 – 410 K; [α]_D²⁵ +52,5° (c 1,02, CHCl₃); ¹H NMR (500 MHz, CDCl₃/TMS), δ (p.p.m.): 7.40–7.35 (m, 5H), 4.88 (dd, ²J = 11.5 Hz, ³J = 5.3 Hz, 1H), 4.77 (dd, ²J = 11.5 Hz, ³J = 7.7 Hz, 1H), 4.43 (AB spin system, Dn = 36.0 Hz, ²J = 15.3 Hz, 2H), 4.40 (dd, ³J = 7.7 Hz, ³J = 5.3 Hz, 1H), 2.81 (s, 3H). ¹H NMR (125 MHz, CDCl₃/TMS), δ (p.p.m.): 166.07, 149.54, 134.69, 129.16, 128.90, 127.02, 67.65, 61.54, 44.75, 42.12. Anal. calcd for C₁₂H₁₃ClN₂O₃: C, 53.64%; H, 4.88%; N, 10.43%. Found: C, 53.46%; H, 4.92%; N, 10.49%.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006); software used to prepare material for publication: MarvinSketch (Chemaxon, 2010) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of (I) showing atom labelling scheme and displacement ellipsoids at the 50% probability level (arbitrary spheres for the H atoms).
	Fig. 2. A view of the unit-cell contents in (I) viewed in projection down the b axis showing the C—H···O interactions as orange dashed lines.

(5R)-3-(2-Chloroacetyl)-4-methyl-5-phenyl-1,3,4-oxadiazinan-2-one top

Crystal data top

C₁₂H₁₃ClN₂O₃	F(000) = 560
M_r = 268.69	D_x = 1.476 Mg m⁻³
Orthorhombic, P2₁2₁2₁	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 2003 reflections
a = 9.4862 (2) Å	θ = 2.8–16.3°
b = 9.6237 (2) Å	µ = 0.32 mm⁻¹
c = 13.2433 (3) Å	T = 100 K
V = 1209.01 (5) Å³	Block, colourless
Z = 4	0.35 × 0.30 × 0.25 mm

Data collection top

Bruker APEXII CCD diffractometer	2334 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.026
Graphite monochromator	θ_max = 26.0°, θ_min = 2.6°
ω scans	h = −11→11
29813 measured reflections	k = −11→11
2378 independent reflections	l = −16→16

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)] = 0.020	H-atom parameters constrained
wR(F²) = 0.054	w = 1/[σ²(F_o²) + (0.028P)² + 0.320P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max = 0.001
2378 reflections	Δρ_max = 0.19 e Å⁻³
164 parameters	Δρ_min = −0.20 e Å⁻³
0 restraints	Absolute structure: Flack (1983), 993 Friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.01 (5)

Crystal data top

C₁₂H₁₃ClN₂O₃	V = 1209.01 (5) Å³
M_r = 268.69	Z = 4
Orthorhombic, P2₁2₁2₁	Mo Kα radiation
a = 9.4862 (2) Å	µ = 0.32 mm⁻¹
b = 9.6237 (2) Å	T = 100 K
c = 13.2433 (3) Å	0.35 × 0.30 × 0.25 mm

Data collection top

Bruker APEXII CCD diffractometer	2334 reflections with I > 2σ(I)
29813 measured reflections	R_int = 0.026
2378 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.020	H-atom parameters constrained
wR(F²) = 0.054	Δρ_max = 0.19 e Å⁻³
S = 1.07	Δρ_min = −0.20 e Å⁻³
2378 reflections	Absolute structure: Flack (1983), 993 Friedel pairs
164 parameters	Absolute structure parameter: 0.01 (5)
0 restraints

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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
Cl	0.24739 (4)	−0.34782 (3)	0.91280 (2)	0.02998 (10)
O1	0.05085 (9)	0.22385 (9)	0.73203 (7)	0.0182 (2)
O2	−0.07381 (9)	0.09934 (10)	0.83862 (7)	0.0196 (2)
O3	0.09385 (10)	−0.08909 (10)	0.93619 (7)	0.0200 (2)
N1	0.13328 (11)	0.00514 (11)	0.77991 (8)	0.0146 (2)
N2	0.22794 (11)	0.00168 (11)	0.69603 (7)	0.0156 (2)
C1	0.02961 (13)	0.10834 (13)	0.78683 (9)	0.0153 (2)
C2	0.28807 (12)	0.14314 (13)	0.68462 (9)	0.0165 (2)
H2	0.3517	0.1421	0.6244	0.020*
C3	0.16885 (13)	0.24374 (14)	0.66273 (9)	0.0184 (3)
H3A	0.2041	0.3402	0.6689	0.022*
H3B	0.1359	0.2301	0.5925	0.022*
C4	0.37768 (13)	0.17604 (13)	0.77675 (9)	0.0163 (2)
C5	0.49224 (13)	0.08997 (14)	0.79745 (10)	0.0200 (3)
H5	0.5116	0.0132	0.7545	0.024*
C6	0.57847 (14)	0.11524 (15)	0.88025 (11)	0.0228 (3)
H6	0.6556	0.0553	0.8942	0.027*
C7	0.55191 (14)	0.22803 (15)	0.94258 (10)	0.0221 (3)
H7	0.6113	0.2458	0.9988	0.027*
C8	0.43859 (15)	0.31474 (13)	0.92274 (10)	0.0212 (3)
H8	0.4203	0.3921	0.9654	0.025*
C9	0.35165 (14)	0.28841 (13)	0.84028 (10)	0.0185 (3)
H9	0.2737	0.3477	0.8272	0.022*
C10	0.15311 (13)	−0.09421 (13)	0.85593 (9)	0.0157 (2)
C11	0.25837 (14)	−0.20626 (13)	0.82638 (9)	0.0194 (3)
H11A	0.3550	−0.1674	0.8271	0.023*
H11B	0.2378	−0.2394	0.7571	0.023*
C12	0.15380 (14)	−0.04923 (14)	0.60530 (9)	0.0195 (3)
H12A	0.1286	−0.1472	0.6146	0.029*
H12B	0.2155	−0.0399	0.5464	0.029*
H12C	0.0680	0.0056	0.5947	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl	0.0483 (2)	0.01763 (15)	0.02398 (16)	0.00875 (16)	−0.00658 (16)	0.00243 (12)
O1	0.0178 (4)	0.0164 (4)	0.0205 (4)	0.0022 (4)	0.0018 (4)	0.0041 (4)
O2	0.0179 (4)	0.0206 (5)	0.0202 (4)	0.0031 (4)	0.0031 (4)	0.0011 (4)
O3	0.0249 (5)	0.0204 (4)	0.0148 (4)	0.0010 (4)	−0.0004 (4)	−0.0004 (4)
N1	0.0149 (5)	0.0139 (5)	0.0150 (5)	−0.0001 (4)	0.0019 (4)	−0.0008 (4)
N2	0.0170 (5)	0.0159 (5)	0.0138 (5)	−0.0026 (4)	0.0035 (4)	−0.0031 (4)
C1	0.0170 (6)	0.0150 (6)	0.0137 (5)	0.0002 (5)	−0.0030 (5)	−0.0017 (5)
C2	0.0177 (6)	0.0157 (6)	0.0162 (5)	−0.0024 (5)	0.0035 (4)	0.0002 (5)
C3	0.0196 (6)	0.0191 (6)	0.0164 (6)	−0.0026 (5)	0.0014 (5)	0.0025 (5)
C4	0.0157 (6)	0.0163 (6)	0.0170 (5)	−0.0050 (5)	0.0035 (5)	0.0016 (5)
C5	0.0160 (6)	0.0195 (6)	0.0245 (7)	−0.0014 (5)	0.0050 (5)	−0.0024 (5)
C6	0.0142 (6)	0.0263 (7)	0.0280 (7)	−0.0014 (5)	0.0016 (5)	0.0039 (6)
C7	0.0200 (6)	0.0271 (7)	0.0193 (6)	−0.0099 (5)	−0.0015 (5)	0.0034 (5)
C8	0.0270 (7)	0.0181 (6)	0.0186 (6)	−0.0052 (5)	0.0019 (5)	−0.0011 (5)
C9	0.0210 (6)	0.0153 (6)	0.0192 (6)	−0.0001 (5)	0.0029 (5)	0.0012 (5)
C10	0.0169 (6)	0.0141 (6)	0.0160 (6)	−0.0031 (5)	−0.0046 (5)	−0.0024 (5)
C11	0.0210 (6)	0.0156 (6)	0.0218 (6)	0.0012 (5)	−0.0027 (5)	0.0017 (5)
C12	0.0233 (7)	0.0199 (6)	0.0154 (6)	−0.0024 (5)	−0.0006 (5)	−0.0034 (5)

Geometric parameters (Å, º) top

Cl—C11	1.7823 (13)	C4—C5	1.3937 (18)
O1—C1	1.3428 (15)	C5—C6	1.3895 (19)
O1—C3	1.4601 (15)	C5—H5	0.9500
O2—C1	1.2001 (15)	C6—C7	1.387 (2)
O3—C10	1.2034 (16)	C6—H6	0.9500
N1—C1	1.4006 (16)	C7—C8	1.386 (2)
N1—C10	1.4012 (16)	C7—H7	0.9500
N1—N2	1.4287 (14)	C8—C9	1.3917 (19)
N2—C12	1.4760 (15)	C8—H8	0.9500
N2—C2	1.4838 (16)	C9—H9	0.9500
C2—C3	1.5167 (18)	C10—C11	1.5209 (17)
C2—C4	1.5203 (17)	C11—H11A	0.9900
C2—H2	1.0000	C11—H11B	0.9900
C3—H3A	0.9900	C12—H12A	0.9800
C3—H3B	0.9900	C12—H12B	0.9800
C4—C9	1.3923 (18)	C12—H12C	0.9800

C1—O1—C3	124.28 (10)	C7—C6—C5	119.99 (12)
C1—N1—C10	122.08 (11)	C7—C6—H6	120.0
C1—N1—N2	120.58 (10)	C5—C6—H6	120.0
C10—N1—N2	117.28 (10)	C8—C7—C6	119.96 (12)
N1—N2—C12	109.95 (9)	C8—C7—H7	120.0
N1—N2—C2	107.42 (9)	C6—C7—H7	120.0
C12—N2—C2	113.88 (10)	C7—C8—C9	119.92 (13)
O2—C1—O1	119.42 (11)	C7—C8—H8	120.0
O2—C1—N1	124.07 (12)	C9—C8—H8	120.0
O1—C1—N1	116.50 (10)	C8—C9—C4	120.70 (12)
N2—C2—C3	108.57 (10)	C8—C9—H9	119.7
N2—C2—C4	108.92 (10)	C4—C9—H9	119.7
C3—C2—C4	115.94 (11)	O3—C10—N1	122.96 (12)
N2—C2—H2	107.7	O3—C10—C11	124.27 (12)
C3—C2—H2	107.7	N1—C10—C11	112.77 (11)
C4—C2—H2	107.7	C10—C11—Cl	109.77 (9)
O1—C3—C2	111.58 (10)	C10—C11—H11A	109.7
O1—C3—H3A	109.3	Cl—C11—H11A	109.7
C2—C3—H3A	109.3	C10—C11—H11B	109.7
O1—C3—H3B	109.3	Cl—C11—H11B	109.7
C2—C3—H3B	109.3	H11A—C11—H11B	108.2
H3A—C3—H3B	108.0	N2—C12—H12A	109.5
C9—C4—C5	118.75 (12)	N2—C12—H12B	109.5
C9—C4—C2	123.20 (12)	H12A—C12—H12B	109.5
C5—C4—C2	118.04 (12)	N2—C12—H12C	109.5
C6—C5—C4	120.68 (12)	H12A—C12—H12C	109.5
C6—C5—H5	119.7	H12B—C12—H12C	109.5
C4—C5—H5	119.7

C1—N1—N2—C12	−74.26 (13)	C3—C2—C4—C9	1.96 (17)
C10—N1—N2—C12	108.57 (12)	N2—C2—C4—C5	59.96 (14)
C1—N1—N2—C2	50.16 (13)	C3—C2—C4—C5	−177.28 (11)
C10—N1—N2—C2	−127.01 (11)	C9—C4—C5—C6	0.36 (19)
C3—O1—C1—O2	−176.89 (11)	C2—C4—C5—C6	179.64 (11)
C3—O1—C1—N1	3.76 (17)	C4—C5—C6—C7	−0.77 (19)
C10—N1—C1—O2	−22.68 (18)	C5—C6—C7—C8	0.57 (19)
N2—N1—C1—O2	160.29 (11)	C6—C7—C8—C9	0.02 (19)
C10—N1—C1—O1	156.64 (11)	C7—C8—C9—C4	−0.42 (19)
N2—N1—C1—O1	−20.39 (16)	C5—C4—C9—C8	0.23 (19)
N1—N2—C2—C3	−61.59 (12)	C2—C4—C9—C8	−179.00 (11)
C12—N2—C2—C3	60.42 (12)	C1—N1—C10—O3	−8.18 (18)
N1—N2—C2—C4	65.49 (12)	N2—N1—C10—O3	168.94 (11)
C12—N2—C2—C4	−172.50 (10)	C1—N1—C10—C11	172.73 (11)
C1—O1—C3—C2	−18.86 (16)	N2—N1—C10—C11	−10.15 (15)
N2—C2—C3—O1	47.44 (13)	O3—C10—C11—Cl	14.29 (16)
C4—C2—C3—O1	−75.51 (14)	N1—C10—C11—Cl	−166.64 (8)
N2—C2—C4—C9	−120.81 (13)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3ⁱ	1.00	2.60	3.5142 (15)	153
C8—H8···O2ⁱⁱ	0.95	2.60	3.2689 (16)	128
C11—H11b···O2ⁱⁱⁱ	0.99	2.54	3.3675 (16)	141
C12—H12a···O2ⁱⁱⁱ	0.98	2.57	3.5448 (16)	173

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

Experimental details

Crystal data
Chemical formula	C₁₂H₁₃ClN₂O₃
M_r	268.69
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	100
a, b, c (Å)	9.4862 (2), 9.6237 (2), 13.2433 (3)
V (Å³)	1209.01 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.32
Crystal size (mm)	0.35 × 0.30 × 0.25

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	29813, 2378, 2334
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.020, 0.054, 1.07
No. of reflections	2378
No. of parameters	164
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.20
Absolute structure	Flack (1983), 993 Friedel pairs
Absolute structure parameter	0.01 (5)

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), MarvinSketch (Chemaxon, 2010) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···O3ⁱ	1.00	2.60	3.5142 (15)	153
C8—H8···O2ⁱⁱ	0.95	2.60	3.2689 (16)	128
C11—H11b···O2ⁱⁱⁱ	0.99	2.54	3.3675 (16)	141
C12—H12a···O2ⁱⁱⁱ	0.98	2.57	3.5448 (16)	173

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

Acknowledgements

We thank the Brazilian agencies FAPESP, CNPq (fellowships 308116/2010–0 to IC and 303544/2009–0 to PRO) and CAPES (808/2009 to IC) for financial support. We also thank Dr Charles H. Lake from Indiana University of Pennsylvania for the data collection during the American Crystallographic Association Summer Course in small molecule crystallography.

References

Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bonin, M., Chauveau, A. & Micouin, L. (2006). Synlett, pp. 2349–2363. CrossRef Google Scholar
Brandenburg, K. (2006). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2007). SAINT and APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Casper, D. M., Blackburn, J. R., Maroules, C. D., Brady, T., Esken, J. M., Ferrence, G. M., Standard, J. M. & Hitchcock, S. R. (2002a). J. Org. Chem. 67, 8871–8876. Web of Science CSD CrossRef PubMed CAS Google Scholar
Casper, D. M., Burgeson, J. R., Esken, J. M., Ferrence, G. M. & Hitchcock, S. R. (2002b). Org. Lett. 4, 3739–3742. Web of Science CSD CrossRef PubMed CAS Google Scholar
Chemaxon (2010). Marvinsketch. http://www.chemaxon.com. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Flack, H. D. (1983). Acta Cryst. A39, 876–881. CrossRef CAS Web of Science IUCr Journals Google Scholar
Rodrigues, A., Olivato, P. R. & Rittner, R. (2005). Synthesis, pp. 2578–2582. Web of Science CrossRef Google Scholar
Roussi, F., Bonin, M., Chiaroni, A., Micouin, L., Riche, C. & Husson, H.-P. (1998). Tetrahedron Lett. 39, 8081–8084. Web of Science CSD CrossRef CAS Google Scholar
Roussi, F., Bonin, M., Chiaroni, A., Micouin, L., Riche, C. & Husson, H.-P. (1999). Tetrahedron Lett. 40, 3727–3730. CrossRef CAS Google Scholar
Roussi, F., Chauveau, A., Bonin, M., Micouin, L. & Husson, H.-P. (2000). Synthesis, pp. 1170–1179. CrossRef Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Trepanier, D. L., Elbe, J. N. & Harris, G. H. (1968). J. Med. Chem. 11, 357–360. CrossRef CAS PubMed Web of Science Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zukerman-Schpector, J., Sousa Madureira, L., Rodrigues, A., Vinhato, E. & Olivato, P. R. (2009). Acta Cryst. E65, o1468. Web of Science CSD CrossRef IUCr Journals Google Scholar