#------------------------------------------------------------------------------
#$Date: 2016-02-20 22:30:07 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176789 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/24/2222474.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_2222474
loop_
_publ_author_name
'Zukerman-Schpector, Julio'
'Sousa Madureira, Lucas'
'Rodrigues, Alessandro'
'Vinhato, Elisângela'
'Olivato, Paulo R.'
_publ_section_title
;
 4-Methyl-3-(2-phenoxyacetyl)-5-phenyl-1,3,4-oxadiazinan-2-one
;
_journal_coeditor_code           TK2466
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1468
_journal_paper_doi               10.1107/S1600536809020285
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C18 H18 N2 O4'
_chemical_formula_moiety         'C18 H18 N2 O4'
_chemical_formula_sum            'C18 H18 N2 O4'
_chemical_formula_weight         326.34
_chemical_melting_point_gt       385
_chemical_melting_point_lt       387
_chemical_name_systematic
;
(5R)-4-Methyl-3-(2-phenoxyacetyl)-5-phenyl-1,3,4-oxadiazinan-2-one
;
_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
_cell_angle_beta                 114.206(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6024(9)
_cell_length_b                   9.4203(10)
_cell_length_c                   19.275(3)
_cell_measurement_reflns_used    24
_cell_measurement_temperature    290(2)
_cell_measurement_theta_max      15.1
_cell_measurement_theta_min      10.5
_cell_volume                     1590.3(4)
_computing_cell_refinement       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_collection       'CAD-4 EXPRESS (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material
;
WinGX (Farrugia, 1999), PARST (Nardelli, 1995) and
MarvinSketch (ChemAxon, 2008)
;
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_diffrn_ambient_temperature      290(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω-2θ
_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  0.030
_diffrn_reflns_av_sigmaI/netI    0.071
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            2971
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         2.3
_diffrn_standards_decay_%        <1
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.23
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.12
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2793
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.12
_refine_ls_R_factor_all          0.156
_refine_ls_R_factor_gt           0.064
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0852P)²+2.8996P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.208
_refine_ls_wR_factor_ref         0.246
_reflns_number_gt                1355
_reflns_number_total             2793
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2466.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2222474
_cod_database_fobs_code          2222474
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.6770(6) 0.3140(6) -0.0050(3) 0.0504(14) Uani d . 1 . .
H H1 0.6177 0.3840 -0.0433 0.060 Uiso calc R 1 . .
C C2 0.5715(6) 0.1861(6) -0.0126(4) 0.0676(18) Uani d . 1 . .
H H2A 0.5123 0.2040 0.0169 0.081 Uiso calc R 1 . .
H H2B 0.5008 0.1758 -0.0655 0.081 Uiso calc R 1 . .
C C3 0.8059(6) 0.0406(6) 0.0376(3) 0.0530(14) Uani d . 1 . .
C C4 1.0422(5) 0.1778(6) 0.0667(3) 0.0411(12) Uani d . 1 . .
C C5 1.0994(5) 0.3123(6) 0.0478(3) 0.0492(13) Uani d . 1 . .
H H5A 1.0756 0.3145 -0.0062 0.059 Uiso calc R 1 . .
H H5B 1.0487 0.3921 0.0593 0.059 Uiso calc R 1 . .
C C6 0.7359(5) 0.3870(6) 0.0714(3) 0.0419(12) Uani d . 1 . .
C C7 0.7468(6) 0.5357(6) 0.0737(3) 0.0550(14) Uani d . 1 . .
H H7 0.7155 0.5862 0.0284 0.066 Uiso calc R 1 . .
C C8 0.8025(8) 0.6080(7) 0.1415(4) 0.0690(18) Uani d . 1 . .
H H8 0.8055 0.7067 0.1416 0.083 Uiso calc R 1 . .
C C9 0.8541(7) 0.5350(9) 0.2091(4) 0.0735(19) Uani d . 1 . .
H H9 0.8956 0.5837 0.2551 0.088 Uiso calc R 1 . .
C C10 0.8439(7) 0.3903(8) 0.2083(3) 0.0643(17) Uani d . 1 . .
H H10 0.8769 0.3407 0.2539 0.077 Uiso calc R 1 . .
C C11 0.7850(6) 0.3167(7) 0.1400(3) 0.0596(16) Uani d . 1 . .
H H11 0.7784 0.2182 0.1405 0.071 Uiso calc R 1 . .
C C12 1.3081(6) 0.3918(6) 0.1593(3) 0.0452(12) Uani d . 1 . .
C C13 1.4569(5) 0.4434(6) 0.1878(3) 0.0498(14) Uani d . 1 . .
H H13 1.5174 0.4293 0.1612 0.060 Uiso calc R 1 . .
C C18 0.7580(7) 0.2267(6) -0.1031(3) 0.0593(16) Uani d . 1 . .
H H18A 0.8470 0.2022 -0.1114 0.089 Uiso calc R 1 . .
H H18B 0.7058 0.3041 -0.1358 0.089 Uiso calc R 1 . .
H H18C 0.6912 0.1461 -0.1141 0.089 Uiso calc R 1 . .
C C14 1.5132(6) 0.5148(6) 0.2553(3) 0.0573(15) Uani d . 1 . .
H H14 1.6120 0.5508 0.2739 0.069 Uiso calc R 1 . .
C C15 1.4279(7) 0.5343(7) 0.2958(3) 0.0640(17) Uani d . 1 . .
H H15 1.4668 0.5849 0.3412 0.077 Uiso calc R 1 . .
C C16 1.2833(7) 0.4782(7) 0.2689(3) 0.0650(16) Uani d . 1 . .
H H16 1.2256 0.4878 0.2973 0.078 Uiso calc R 1 . .
C C17 1.2231(6) 0.4082(6) 0.2007(3) 0.0544(14) Uani d . 1 . .
H H17 1.1244 0.3719 0.1826 0.065 Uiso calc R 1 . .
N N1 0.8837(4) 0.1580(4) 0.0262(2) 0.0420(10) Uani d . 1 . .
N N2 0.8042(4) 0.2689(4) -0.0233(2) 0.0383(10) Uani d . 1 . .
O O1 0.6553(4) 0.0565(4) 0.0129(3) 0.0744(13) Uani d . 1 . .
O O2 0.8648(5) -0.0680(4) 0.0671(3) 0.0712(12) Uani d . 1 . .
O O3 1.1208(4) 0.0946(4) 0.1131(2) 0.0611(11) Uani d . 1 . .
O O4 1.2593(4) 0.3245(4) 0.0898(2) 0.0569(11) Uani d . 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 C1 C6 . . 110.6(4) ?
N2 C1 C2 . . 109.3(4) ?
C6 C1 C2 . . 114.7(5) ?
N2 C1 H1 . . 107.3 ?
C6 C1 H1 . . 107.3 ?
C2 C1 H1 . . 107.3 ?
O1 C2 C1 . . 112.2(4) ?
O1 C2 H2A . . 109.2 ?
C1 C2 H2A . . 109.2 ?
O1 C2 H2B . . 109.2 ?
C1 C2 H2B . . 109.2 ?
H2A C2 H2B . . 107.9 ?
O2 C3 O1 . . 119.9(5) ?
O2 C3 N1 . . 124.9(5) ?
O1 C3 N1 . . 115.2(5) ?
O3 C4 N1 . . 122.3(5) ?
O3 C4 C5 . . 124.0(5) ?
N1 C4 C5 . . 113.6(4) ?
O4 C5 C4 . . 110.6(4) ?
O4 C5 H5A . . 109.5 ?
C4 C5 H5A . . 109.5 ?
O4 C5 H5B . . 109.5 ?
C4 C5 H5B . . 109.5 ?
H5A C5 H5B . . 108.1 ?
C11 C6 C7 . . 117.3(5) ?
C11 C6 C1 . . 124.1(5) ?
C7 C6 C1 . . 118.6(5) ?
C8 C7 C6 . . 121.4(6) ?
C8 C7 H7 . . 119.3 ?
C6 C7 H7 . . 119.3 ?
C7 C8 C9 . . 120.2(6) ?
C7 C8 H8 . . 119.9 ?
C9 C8 H8 . . 119.9 ?
C10 C9 C8 . . 119.5(6) ?
C10 C9 H9 . . 120.3 ?
C8 C9 H9 . . 120.3 ?
C9 C10 C11 . . 120.6(6) ?
C9 C10 H10 . . 119.7 ?
C11 C10 H10 . . 119.7 ?
C6 C11 C10 . . 121.1(6) ?
C6 C11 H11 . . 119.5 ?
C10 C11 H11 . . 119.5 ?
C17 C12 O4 . . 125.0(5) ?
C17 C12 C13 . . 119.5(5) ?
O4 C12 C13 . . 115.5(5) ?
C14 C13 C12 . . 119.4(5) ?
C14 C13 H13 . . 120.3 ?
C12 C13 H13 . . 120.3 ?
N2 C18 H18A . . 109.5 ?
N2 C18 H18B . . 109.5 ?
H18A C18 H18B . . 109.5 ?
N2 C18 H18C . . 109.5 ?
H18A C18 H18C . . 109.5 ?
H18B C18 H18C . . 109.5 ?
C15 C14 C13 . . 121.3(5) ?
C15 C14 H14 . . 119.4 ?
C13 C14 H14 . . 119.4 ?
C14 C15 C16 . . 119.1(5) ?
C14 C15 H15 . . 120.5 ?
C16 C15 H15 . . 120.5 ?
C17 C16 C15 . . 120.8(6) ?
C17 C16 H16 . . 119.6 ?
C15 C16 H16 . . 119.6 ?
C12 C17 C16 . . 119.8(5) ?
C12 C17 H17 . . 120.1 ?
C16 C17 H17 . . 120.1 ?
C3 N1 N2 . . 121.0(4) ?
C3 N1 C4 . . 122.8(4) ?
N2 N1 C4 . . 116.0(4) ?
N1 N2 C1 . . 109.0(4) ?
N1 N2 C18 . . 110.8(4) ?
C1 N2 C18 . . 114.0(4) ?
C3 O1 C2 . . 126.3(4) ?
C12 O4 C5 . . 116.7(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 N2 . 1.466(6) ?
C1 C6 . 1.511(7) ?
C1 C2 . 1.542(8) ?
C1 H1 . 0.9800 ?
C2 O1 . 1.433(7) ?
C2 H2A . 0.9700 ?
C2 H2B . 0.9700 ?
C3 O2 . 1.194(6) ?
C3 O1 . 1.332(6) ?
C3 N1 . 1.402(7) ?
C4 O3 . 1.195(6) ?
C4 N1 . 1.410(6) ?
C4 C5 . 1.484(7) ?
C5 O4 . 1.417(6) ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C6 C11 . 1.378(7) ?
C6 C7 . 1.404(8) ?
C7 C8 . 1.372(8) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.374(9) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.366(9) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.386(8) ?
C10 H10 . 0.9300 ?
C11 H11 . 0.9300 ?
C12 C17 . 1.365(7) ?
C12 O4 . 1.378(6) ?
C12 C13 . 1.391(7) ?
C13 C14 . 1.364(8) ?
C13 H13 . 0.9300 ?
C18 N2 . 1.469(6) ?
C18 H18A . 0.9600 ?
C18 H18B . 0.9600 ?
C18 H18C . 0.9600 ?
C14 C15 . 1.355(9) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.373(8) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.369(7) ?
C16 H16 . 0.9300 ?
C17 H17 . 0.9300 ?
N1 N2 . 1.410(5) ?
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
_geom_hbond_publ_flag
C7 H7 O4 3_765 0.93 2.53 3.394(7) 154 y
C9 H9 O3 2_755 0.93 2.61 3.383(8) 141 y
C13 H13 Cg2 1_655 0.93 2.86 3.715(6) 153 y
C18 H18B Cg3 3_765 0.96 2.74 3.672(6) 165 y
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N2 C1 C2 O1 . . . . 37.4(7) ?
C6 C1 C2 O1 . . . . -87.4(6) ?
O3 C4 C5 O4 . . . . 2.4(7) ?
N1 C4 C5 O4 . . . . -179.3(4) ?
N2 C1 C6 C11 . . . . -82.9(6) ?
C2 C1 C6 C11 . . . . 41.2(7) ?
N2 C1 C6 C7 . . . . 94.9(6) ?
C2 C1 C6 C7 . . . . -141.0(5) ?
C11 C6 C7 C8 . . . . -0.6(8) ?
C1 C6 C7 C8 . . . . -178.5(5) ?
C6 C7 C8 C9 . . . . 2.2(9) ?
C7 C8 C9 C10 . . . . -2.5(10) ?
C8 C9 C10 C11 . . . . 1.2(10) ?
C7 C6 C11 C10 . . . . -0.6(8) ?
C1 C6 C11 C10 . . . . 177.1(5) ?
C9 C10 C11 C6 . . . . 0.3(9) ?
C17 C12 C13 C14 . . . . -2.7(8) ?
O4 C12 C13 C14 . . . . 178.3(5) ?
C12 C13 C14 C15 . . . . 1.2(9) ?
C13 C14 C15 C16 . . . . 1.4(9) ?
C14 C15 C16 C17 . . . . -2.5(10) ?
O4 C12 C17 C16 . . . . -179.5(5) ?
C13 C12 C17 C16 . . . . 1.6(9) ?
C15 C16 C17 C12 . . . . 1.0(10) ?
O2 C3 N1 N2 . . . . 165.9(5) ?
O1 C3 N1 N2 . . . . -14.2(7) ?
O2 C3 N1 C4 . . . . -18.8(9) ?
O1 C3 N1 C4 . . . . 161.1(5) ?
O3 C4 N1 C3 . . . . 0.8(8) ?
C5 C4 N1 C3 . . . . -177.6(5) ?
O3 C4 N1 N2 . . . . 176.3(4) ?
C5 C4 N1 N2 . . . . -2.0(6) ?
C3 N1 N2 C1 . . . . 49.4(6) ?
C4 N1 N2 C1 . . . . -126.2(4) ?
C3 N1 N2 C18 . . . . -76.8(6) ?
C4 N1 N2 C18 . . . . 107.6(5) ?
C6 C1 N2 N1 . . . . 68.9(5) ?
C2 C1 N2 N1 . . . . -58.2(5) ?
C6 C1 N2 C18 . . . . -166.8(4) ?
C2 C1 N2 C18 . . . . 66.1(6) ?
O2 C3 O1 C2 . . . . 169.7(6) ?
N1 C3 O1 C2 . . . . -10.2(9) ?
C1 C2 O1 C3 . . . . -3.0(9) ?
C17 C12 O4 C5 . . . . 21.0(8) ?
C13 C12 O4 C5 . . . . -160.0(5) ?
C4 C5 O4 C12 . . . . -90.5(6) ?
