#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/36/2213610.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_2213610
loop_
_publ_author_name
'Hong-Gang Li'
'Jian-Min Dou'
'Da-Cheng Li'
'Da-Qi Wang'
_publ_section_title
;
 Isopropyl 2-oxo-3,4-dihydro-1,4-benzoxazine-4-acetate
;
_journal_coeditor_code           XU2224
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2542
_journal_page_last               o2543
_journal_paper_doi               10.1107/S1600536807016935
_journal_volume                  63
_journal_year                    2007
_chemical_formula_iupac          'C13 H15 N O4'
_chemical_formula_moiety         'C13 H15 N O4'
_chemical_formula_sum            'C13 H15 N O4'
_chemical_formula_weight         249.26
_chemical_name_systematic
;
Isopropyl 2-oxo-3,4-dihydro-1,4-benzoxazine-4-acetate
;
_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                 108.349(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.632(6)
_cell_length_b                   9.587(4)
_cell_length_c                   10.240(5)
_cell_measurement_reflns_used    1010
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.6
_cell_measurement_theta_min      2.6
_cell_volume                     1270.2(10)
_computing_cell_refinement       'SAINT (Siemens, 1996)'
_computing_data_collection       'SMART (Siemens, 1996)'
_computing_data_reduction        SAINT
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1997b)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997a)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997a)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 1.00
_diffrn_measured_fraction_theta_max 1.00
_diffrn_measurement_device_type  'Bruker 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  0.052
_diffrn_reflns_av_sigmaI/netI    0.166
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6376
_diffrn_reflns_theta_full        25.0
_diffrn_reflns_theta_max         25.0
_diffrn_reflns_theta_min         1.5
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rectangle
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.39
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.17
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2234
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.000
_refine_ls_R_factor_all          0.125
_refine_ls_R_factor_gt           0.057
_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)+(0.116P)²+0.2459P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.171
_refine_ls_wR_factor_ref         0.274
_reflns_number_gt                1134
_reflns_number_total             2234
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            xu2224.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2213610
_cod_database_fobs_code          2213610
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
N N1 0.3795(2) 0.4579(3) 0.4064(3) 0.0504(9) Uani d . 1
O O2 0.5507(2) 0.5936(3) 0.2382(3) 0.0730(10) Uani d . 1
O O3 0.17099(19) 0.2136(3) 0.3604(3) 0.0645(9) Uani d . 1
O O4 0.1893(2) 0.3773(3) 0.2144(4) 0.0898(12) Uani d . 1
C C8 0.4229(3) 0.4595(4) 0.2946(5) 0.0578(11) Uani d . 1
H H8A 0.3673 0.4491 0.2086 0.069 Uiso calc R 1
H H8B 0.4684 0.3797 0.3041 0.069 Uiso calc R 1
C C7 0.4820(3) 0.5881(4) 0.2873(5) 0.0549(11) Uani d . 1
O O1 0.4533(2) 0.7072(2) 0.3347(3) 0.0577(8) Uani d . 1
C C1 0.3738(3) 0.7076(4) 0.3932(4) 0.0497(10) Uani d . 1
C C2 0.3360(3) 0.5839(4) 0.4300(4) 0.0490(10) Uani d . 1
C C3 0.2629(3) 0.5947(4) 0.4971(5) 0.0647(12) Uani d . 1
H H3 0.2373 0.5142 0.5252 0.078 Uiso calc R 1
C C4 0.2274(4) 0.7233(5) 0.5229(5) 0.0769(14) Uani d . 1
H H4 0.1784 0.7286 0.5687 0.092 Uiso calc R 1
C C5 0.2638(4) 0.8436(5) 0.4814(5) 0.0759(14) Uani d . 1
H H5 0.2385 0.9299 0.4972 0.091 Uiso calc R 1
C C6 0.3375(3) 0.8357(4) 0.4165(5) 0.0645(12) Uani d . 1
H H6 0.3627 0.9166 0.3885 0.077 Uiso calc R 1
C C9 0.2224(3) 0.3115(4) 0.3186(4) 0.0545(10) Uani d . 1
C C10 0.3292(3) 0.3288(4) 0.4217(4) 0.0538(11) Uani d . 1
H H10A 0.3237 0.3249 0.5138 0.065 Uiso calc R 1
H H10B 0.3721 0.2513 0.4119 0.065 Uiso calc R 1
C C11 0.0660(3) 0.1809(4) 0.2702(5) 0.0643(12) Uani d . 1
H H11 0.0339 0.2647 0.2199 0.077 Uiso calc R 1
C C12 0.0082(4) 0.1356(7) 0.3651(7) 0.111(2) Uani d . 1
H H12A 0.0389 0.0521 0.4123 0.166 Uiso calc R 1
H H12B -0.0626 0.1177 0.3129 0.166 Uiso calc R 1
H H12C 0.0111 0.2080 0.4310 0.166 Uiso calc R 1
C C13 0.0729(4) 0.0712(6) 0.1723(6) 0.1020(19) Uani d . 1
H H13A 0.1116 0.1056 0.1153 0.153 Uiso calc R 1
H H13B 0.0046 0.0460 0.1157 0.153 Uiso calc R 1
H H13C 0.1069 -0.0092 0.2223 0.153 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'
N N 0.0061 0.0033 '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
C2 N1 C8 115.4(3)
C2 N1 C10 118.6(3)
C8 N1 C10 114.9(3)
C9 O3 C11 117.3(3)
N1 C8 C7 114.3(3)
N1 C8 H8A 108.7
C7 C8 H8A 108.7
N1 C8 H8B 108.7
C7 C8 H8B 108.7
H8A C8 H8B 107.6
O2 C7 O1 118.0(3)
O2 C7 C8 124.5(4)
O1 C7 C8 117.5(3)
C7 O1 C1 120.7(3)
C6 C1 C2 122.0(4)
C6 C1 O1 116.7(3)
C2 C1 O1 121.3(3)
C3 C2 C1 117.3(3)
C3 C2 N1 124.2(3)
C1 C2 N1 118.4(3)
C2 C3 C4 120.9(4)
C2 C3 H3 119.5
C4 C3 H3 119.5
C5 C4 C3 120.5(4)
C5 C4 H4 119.8
C3 C4 H4 119.8
C6 C5 C4 119.7(4)
C6 C5 H5 120.2
C4 C5 H5 120.2
C5 C6 C1 119.6(4)
C5 C6 H6 120.2
C1 C6 H6 120.2
O4 C9 O3 125.0(4)
O4 C9 C10 125.0(4)
O3 C9 C10 110.1(3)
N1 C10 C9 113.7(3)
N1 C10 H10A 108.8
C9 C10 H10A 108.8
N1 C10 H10B 108.8
C9 C10 H10B 108.8
H10A C10 H10B 107.7
O3 C11 C13 108.7(4)
O3 C11 C12 105.2(4)
C13 C11 C12 113.2(4)
O3 C11 H11 109.9
C13 C11 H11 109.9
C12 C11 H11 109.9
C11 C12 H12A 109.5
C11 C12 H12B 109.5
H12A C12 H12B 109.5
C11 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C11 C13 H13A 109.5
C11 C13 H13B 109.5
H13A C13 H13B 109.5
C11 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C2 1.400(4)
N1 C8 1.445(5)
N1 C10 1.447(4)
O2 C7 1.196(4)
O3 C9 1.321(4)
O3 C11 1.472(5)
O4 C9 1.198(5)
C8 C7 1.487(5)
C8 H8A 0.9700
C8 H8B 0.9700
C7 O1 1.346(4)
O1 C1 1.393(4)
C1 C6 1.373(5)
C1 C2 1.392(5)
C2 C3 1.380(5)
C3 C4 1.380(5)
C3 H3 0.9300
C4 C5 1.375(6)
C4 H4 0.9300
C5 C6 1.370(6)
C5 H5 0.9300
C6 H6 0.9300
C9 C10 1.515(5)
C10 H10A 0.9700
C10 H10B 0.9700
C11 C13 1.476(6)
C11 C12 1.495(7)
C11 H11 0.9800
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
C13 H13A 0.9600
C13 H13B 0.9600
C13 H13C 0.9600
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
C6 H6 O2 2_655 0.93 2.63 3.531(5) 163
C8 H8B O1 2_645 0.97 2.62 3.443(5) 143
C10 H10B O2 2_645 0.97 2.60 3.483(5) 151
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21124561
