#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/30/2213093.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2213093
loop_
_publ_author_name
'Le Dai'
'Fen-Er Chen'
'Min-Qin Chen'
_publ_section_title
;
 (5R,6R)-Methyl
 6-methyl-2-phenyl-5,6-dihydro-4H-1,3-oxazine-5-carboxylate
;
_journal_coeditor_code           AT2263
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2365
_journal_page_last               o2366
_journal_paper_doi               10.1107/S1600536807015991
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C13 H15 N O3'
_chemical_formula_moiety         'C13 H15 N O3'
_chemical_formula_sum            'C13 H15 N O3'
_chemical_formula_weight         233.26
_chemical_name_systematic
;
(5R,6R)-Methyl
6-methyl-2-phenyl-5,6-dihydro-4H-1,3-oxazine-5-carboxylate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.501(13)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.095(4)
_cell_length_b                   6.318(3)
_cell_length_c                   23.940(10)
_cell_measurement_reflns_used    824
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.890
_cell_measurement_theta_min      3.339
_cell_volume                     1199.8(10)
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_collection       'SMART (Bruker, 2000)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Bruker, 2000)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0260
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            5176
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         1.74
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.9909
_exptl_absorpt_correction_T_min  0.9774
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.168
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2337
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0457
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0738P)²+0.1037P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1246
_refine_ls_wR_factor_ref         0.1369
_reflns_number_gt                1714
_reflns_number_total             2337
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2263.cif
_cod_data_source_block           I
_cod_original_cell_volume        1199.9(9)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2213093
_cod_database_fobs_code          2213093
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 0.79653(15) -0.16077(16) -0.01554(4) 0.0470(3) Uani d . 1
C C2 0.7870(2) -0.3088(2) 0.02542(6) 0.0401(4) Uani d . 1
N N3 0.7540(2) -0.5032(2) 0.01796(6) 0.0521(4) Uani d . 1
C C4 0.7208(3) -0.5922(3) -0.03945(7) 0.0545(5) Uani d . 1
H H4A 0.6009 -0.6189 -0.0512 0.065 Uiso calc R 1
H H4B 0.7787 -0.7269 -0.0388 0.065 Uiso calc R 1
C C5 0.7773(2) -0.4479(2) -0.08325(6) 0.0444(4) Uani d . 1
H H5 0.9008 -0.4500 -0.0753 0.053 Uiso calc R 1
C C6 0.7238(2) -0.2205(2) -0.07377(6) 0.0417(4) Uani d . 1
H H6 0.7719 -0.1281 -0.0993 0.050 Uiso calc R 1
C C7 0.82312(19) -0.2165(2) 0.08373(6) 0.0407(4) Uani d . 1
C C8 0.8823(2) -0.0120(3) 0.09440(7) 0.0485(4) Uani d . 1
H H8 0.9008 0.0725 0.0644 0.058 Uiso calc R 1
C C9 0.9143(2) 0.0677(3) 0.14936(8) 0.0595(5) Uani d . 1
H H9 0.9564 0.2042 0.1562 0.071 Uiso calc R 1
C C10 0.8841(3) -0.0545(3) 0.19416(8) 0.0638(5) Uani d . 1
H H10 0.9053 -0.0005 0.2310 0.077 Uiso calc R 1
C C11 0.8223(3) -0.2569(3) 0.18379(8) 0.0645(5) Uani d . 1
H H11 0.8002 -0.3387 0.2138 0.077 Uiso calc R 1
C C12 0.7927(2) -0.3391(3) 0.12927(7) 0.0544(5) Uani d . 1
H H12 0.7525 -0.4766 0.1228 0.065 Uiso calc R 1
C C13 0.7197(2) -0.5174(3) -0.14427(7) 0.0507(4) Uani d . 1
O O2 0.7028(3) -0.4016(2) -0.18470(6) 0.0899(6) Uani d . 1
O O3 0.69404(18) -0.72404(19) -0.14857(5) 0.0634(4) Uani d . 1
C C14 0.6408(3) -0.8125(3) -0.20512(8) 0.0736(6) Uani d . 1
H H14A 0.5262 -0.7723 -0.2201 0.110 Uiso calc R 1
H H14B 0.6489 -0.9639 -0.2031 0.110 Uiso calc R 1
H H14C 0.7121 -0.7597 -0.2296 0.110 Uiso calc R 1
C C15 0.5358(2) -0.1832(3) -0.08496(8) 0.0571(5) Uani d . 1
H H15A 0.4854 -0.2747 -0.0610 0.086 Uiso calc R 1
H H15B 0.4886 -0.2128 -0.1242 0.086 Uiso calc R 1
H H15C 0.5139 -0.0384 -0.0767 0.086 Uiso calc R 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C2 O1 C6 116.14(12) y
N3 C2 O1 127.19(15) y
N3 C2 C7 120.73(14) y
O1 C2 C7 112.08(13) y
C2 N3 C4 120.16(13) y
N3 C4 C5 113.09(14) y
N3 C4 H4A 109.0 ?
C5 C4 H4A 109.0 ?
N3 C4 H4B 109.0 ?
C5 C4 H4B 109.0 ?
H4A C4 H4B 107.8 ?
C13 C5 C4 114.47(14) y
C13 C5 C6 112.02(13) y
C4 C5 C6 109.05(14) y
C13 C5 H5 107.0 ?
C4 C5 H5 107.0 ?
C6 C5 H5 107.0 ?
O1 C6 C15 109.34(13) y
O1 C6 C5 108.31(12) y
C15 C6 C5 115.17(14) y
O1 C6 H6 107.9 ?
C15 C6 H6 107.9 ?
C5 C6 H6 107.9 ?
C8 C7 C12 118.80(15) ?
C8 C7 C2 122.37(14) ?
C12 C7 C2 118.82(15) ?
C9 C8 C7 120.47(16) ?
C9 C8 H8 119.8 ?
C7 C8 H8 119.8 ?
C10 C9 C8 120.39(18) ?
C10 C9 H9 119.8 ?
C8 C9 H9 119.8 ?
C11 C10 C9 119.52(17) ?
C11 C10 H10 120.2 ?
C9 C10 H10 120.2 ?
C10 C11 C12 120.53(17) ?
C10 C11 H11 119.7 ?
C12 C11 H11 119.7 ?
C11 C12 C7 120.26(17) ?
C11 C12 H12 119.9 ?
C7 C12 H12 119.9 ?
O2 C13 O3 123.26(16) ?
O2 C13 C5 124.61(17) ?
O3 C13 C5 112.10(14) ?
C13 O3 C14 117.79(14) ?
O3 C14 H14A 109.5 ?
O3 C14 H14B 109.5 ?
H14A C14 H14B 109.5 ?
O3 C14 H14C 109.5 ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
C6 C15 H15A 109.5 ?
C6 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
C6 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C2 1.3682(18) y
O1 C6 1.4511(18) y
C2 N3 1.262(2) y
C2 C7 1.487(2) y
N3 C4 1.460(2) y
C4 C5 1.527(2) y
C4 H4A 0.9700 ?
C4 H4B 0.9700 ?
C5 C13 1.507(2) y
C5 C6 1.530(2) y
C5 H5 0.9800 ?
C6 C15 1.510(2) y
C6 H6 0.9800 ?
C7 C8 1.384(2) ?
C7 C12 1.399(2) ?
C8 C9 1.384(2) ?
C8 H8 0.9300 ?
C9 C10 1.382(3) ?
C9 H9 0.9300 ?
C10 C11 1.377(3) ?
C10 H10 0.9300 ?
C11 C12 1.381(3) ?
C11 H11 0.9300 ?
C12 H12 0.9300 ?
C13 O2 1.199(2) ?
C13 O3 1.323(2) ?
O3 C14 1.448(2) ?
C14 H14A 0.9599 ?
C14 H14B 0.9599 ?
C14 H14C 0.9599 ?
C15 H15A 0.9599 ?
C15 H15B 0.9599 ?
C15 H15C 0.9599 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C15 H15B O2 . 0.96 2.74 3.274(3) 115.6
C6 H6 O3 1_565 0.98 2.83 3.596(2) 135.6
C10 H10 O2 4_556 0.93 2.91 3.513(3) 123.9
C14 H14A O2 2_644 0.96 2.76 3.477(3) 132.2
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_publ_flag
C6 O1 C2 N3 15.4(2) ?
C6 O1 C2 C7 -165.24(12) ?
O1 C2 N3 C4 0.0(3) ?
C7 C2 N3 C4 -179.27(15) ?
C2 N3 C4 C5 15.8(3) ?
N3 C4 C5 C13 -170.40(15) ?
N3 C4 C5 C6 -44.0(2) ?
C2 O1 C6 C15 82.49(16) ?
C2 O1 C6 C5 -43.73(17) ?
C13 C5 C6 O1 -175.12(13) ?
C4 C5 C6 O1 57.12(17) ?
C13 C5 C6 C15 62.14(18) y
C4 C5 C6 C15 -65.62(18) ?
N3 C2 C7 C8 170.87(16) y
O1 C2 C7 C8 -8.5(2) y
N3 C2 C7 C12 -10.5(2) ?
O1 C2 C7 C12 170.09(14) ?
C12 C7 C8 C9 1.4(2) ?
C2 C7 C8 C9 -179.98(15) ?
C7 C8 C9 C10 -1.4(3) ?
C8 C9 C10 C11 0.2(3) ?
C9 C10 C11 C12 0.9(3) ?
C10 C11 C12 C7 -0.9(3) ?
C8 C7 C12 C11 -0.3(3) ?
C2 C7 C12 C11 -178.94(16) ?
C4 C5 C13 O2 155.5(2) ?
C6 C5 C13 O2 30.7(3) ?
C4 C5 C13 O3 -26.4(2) ?
C6 C5 C13 O3 -151.16(15) ?
O2 C13 O3 C14 -0.9(3) ?
C5 C13 O3 C14 -179.00(16) ?
