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#$Date: 2022-06-13 12:38:33 +0300 (Mon, 13 Jun 2022) $
#$Revision: 276000 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/54/8105405.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8105405
loop_
_publ_author_name
'Hoang, Minh-Tu'
'Guo, Ke-Liang'
'Ye, Fei'
_publ_section_title
;
 Crystal structure of
 2-(3,6-dimethyl-2,3-dihydro-4H-benzo[b][1,4]oxazin-4-yl)-2-oxoethyl
 acetate, C14H17NO4
;
_journal_issue                   5
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              1151
_journal_page_last               1153
_journal_paper_doi               10.1515/ncrs-2020-0215
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C14 H17 N O4'
_chemical_formula_sum            'C14 H17 N O4'
_chemical_formula_weight         263.29
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        '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                 112.31(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6719(19)
_cell_length_b                   13.529(3)
_cell_length_c                   11.094(2)
_cell_measurement_reflns_used    9876
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      37.47
_cell_measurement_theta_min      3.01
_cell_volume                     1343.0(5)
_computing_cell_refinement       'RAPID-AUTO (Rigaku 1998 RAPID-AUTO)'
_computing_data_collection       'RAPID-AUTO (Rigaku 1998 RAPID-AUTO)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC, 2002)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXL-97
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  "'Rigaku RAXIS-RAPID"
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_sigmaI/netI    0.0456
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            12727
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         3.01
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_T_max  0.9786
_exptl_absorpt_correction_T_min  0.9608
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Higashi, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.384
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.094
_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     175
_refine_ls_number_reflns         3076
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0480
_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)+(0.0915P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1327
_refine_ls_wR_factor_ref         0.1422
_reflns_number_gt                2280
_reflns_number_total             3076
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2020-0215_suppl.cif
_cod_data_source_block           54
_cod_original_cell_volume        1342.9(5)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               8105405
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
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_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.75381(14) 0.96869(9) 0.93020(11) 0.0307(3) Uani 1 1 d . . .
C2 C 0.69357(15) 0.87873(10) 0.87225(12) 0.0352(3) Uani 1 1 d . . .
H2 H 0.6277 0.8782 0.7856 0.042 Uiso 1 1 calc R . .
C3 C 0.72915(16) 0.78984(10) 0.94032(14) 0.0396(3) Uani 1 1 d . . .
C4 C 0.82288(17) 0.79365(11) 1.07181(14) 0.0435(4) Uani 1 1 d . . .
H4 H 0.8485 0.7352 1.1193 0.052 Uiso 1 1 calc R . .
C5 C 0.87836(16) 0.88196(12) 1.13293(13) 0.0420(4) Uani 1 1 d . . .
H5 H 0.9382 0.8827 1.2213 0.050 Uiso 1 1 calc R . .
C6 C 0.84522(15) 0.96999(10) 1.06313(12) 0.0347(3) Uani 1 1 d . . .
C7 C 0.6639(2) 0.69374(13) 0.87467(19) 0.0602(5) Uani 1 1 d . . .
H7A H 0.7416 0.6451 0.8942 0.090 Uiso 1 1 calc R . .
H7B H 0.6190 0.7036 0.7821 0.090 Uiso 1 1 calc R . .
H7C H 0.5893 0.6713 0.9059 0.090 Uiso 1 1 calc R . .
C8 C 0.86794(17) 1.14674(12) 1.06119(14) 0.0439(4) Uani 1 1 d . . .
H8A H 0.9434 1.1601 1.0256 0.053 Uiso 1 1 calc R . .
H8B H 0.8704 1.2001 1.1204 0.053 Uiso 1 1 calc R . .
C9 C 0.71531(16) 1.14368(10) 0.95122(13) 0.0380(3) Uani 1 1 d . . .
H9 H 0.7007 1.2056 0.9022 0.046 Uiso 1 1 calc R . .
C10 C 0.58818(18) 1.13239(12) 0.99894(16) 0.0465(4) Uani 1 1 d . . .
H10A H 0.4955 1.1250 0.9256 0.070 Uiso 1 1 calc R . .
H10B H 0.5834 1.1900 1.0478 0.070 Uiso 1 1 calc R . .
H10C H 0.6053 1.0750 1.0536 0.070 Uiso 1 1 calc R . .
C11 C 0.73669(14) 1.08503(10) 0.75063(12) 0.0327(3) Uani 1 1 d . . .
C12 C 0.75386(16) 1.00020(11) 0.66755(12) 0.0359(3) Uani 1 1 d . . .
H12A H 0.8128 0.9479 0.7234 0.043 Uiso 1 1 calc R . .
H12B H 0.6563 0.9735 0.6154 0.043 Uiso 1 1 calc R . .
C13 C 0.73790(18) 1.07214(11) 0.46722(13) 0.0422(4) Uani 1 1 d . . .
C14 C 0.8295(3) 1.10051(16) 0.39087(18) 0.0692(6) Uani 1 1 d . . .
H14A H 0.7702 1.1397 0.3173 0.104 Uiso 1 1 calc R . .
H14B H 0.8628 1.0420 0.3610 0.104 Uiso 1 1 calc R . .
H14C H 0.9145 1.1381 0.4451 0.104 Uiso 1 1 calc R . .
N1 N 0.71857(13) 1.06167(8) 0.86435(10) 0.0339(3) Uani 1 1 d . . .
O1 O 0.90217(12) 1.05515(8) 1.13190(9) 0.0447(3) Uani 1 1 d . . .
O2 O 0.73652(13) 1.16995(8) 0.71547(10) 0.0477(3) Uani 1 1 d . . .
O3 O 0.82596(11) 1.03446(8) 0.58399(9) 0.0402(3) Uani 1 1 d . . .
O4 O 0.60512(15) 1.07898(11) 0.43190(11) 0.0673(4) Uani 1 1 d . . .
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.'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 C6 118.77(12) . .
C2 C1 N1 123.71(11) . .
C6 C1 N1 117.33(12) . .
C3 C2 C1 121.96(12) . .
C3 C2 H2 119.0 . .
C1 C2 H2 119.0 . .
C2 C3 C4 117.63(13) . .
C2 C3 C7 120.75(14) . .
C4 C3 C7 121.58(14) . .
C5 C4 C3 121.55(13) . .
C5 C4 H4 119.2 . .
C3 C4 H4 119.2 . .
C4 C5 C6 120.29(13) . .
C4 C5 H5 119.9 . .
C6 C5 H5 119.9 . .
O1 C6 C5 116.70(12) . .
O1 C6 C1 123.60(12) . .
C5 C6 C1 119.67(13) . .
C3 C7 H7A 109.5 . .
C3 C7 H7B 109.5 . .
H7A C7 H7B 109.5 . .
C3 C7 H7C 109.5 . .
H7A C7 H7C 109.5 . .
H7B C7 H7C 109.5 . .
O1 C8 C9 111.58(12) . .
O1 C8 H8A 109.3 . .
C9 C8 H8A 109.3 . .
O1 C8 H8B 109.3 . .
C9 C8 H8B 109.3 . .
H8A C8 H8B 108.0 . .
N1 C9 C8 106.84(11) . .
N1 C9 C10 111.85(12) . .
C8 C9 C10 113.05(12) . .
N1 C9 H9 108.3 . .
C8 C9 H9 108.3 . .
C10 C9 H9 108.3 . .
C9 C10 H10A 109.5 . .
C9 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C9 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
O2 C11 N1 121.85(12) . .
O2 C11 C12 120.49(11) . .
N1 C11 C12 117.65(11) . .
O3 C12 C11 109.88(11) . .
O3 C12 H12A 109.7 . .
C11 C12 H12A 109.7 . .
O3 C12 H12B 109.7 . .
C11 C12 H12B 109.7 . .
H12A C12 H12B 108.2 . .
O4 C13 O3 123.45(13) . .
O4 C13 C14 126.18(15) . .
O3 C13 C14 110.35(14) . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C11 N1 C1 125.63(11) . .
C11 N1 C9 117.87(11) . .
C1 N1 C9 112.80(10) . .
C6 O1 C8 117.30(11) . .
C13 O3 C12 117.26(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.3962(19) .
C1 C6 1.4024(18) .
C1 N1 1.4294(16) .
C2 C3 1.3919(19) .
C2 H2 0.9300 .
C3 C4 1.396(2) .
C3 C7 1.507(2) .
C4 C5 1.378(2) .
C4 H4 0.9300 .
C5 C6 1.390(2) .
C5 H5 0.9300 .
C6 O1 1.3762(17) .
C7 H7A 0.9600 .
C7 H7B 0.9600 .
C7 H7C 0.9600 .
C8 O1 1.4364(19) .
C8 C9 1.517(2) .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C9 N1 1.4779(17) .
C9 C10 1.520(2) .
C9 H9 0.9800 .
C10 H10A 0.9600 .
C10 H10B 0.9600 .
C10 H10C 0.9600 .
C11 O2 1.2131(17) .
C11 N1 1.3748(16) .
C11 C12 1.5200(19) .
C12 O3 1.4323(16) .
C12 H12A 0.9700 .
C12 H12B 0.9700 .
C13 O4 1.196(2) .
C13 O3 1.3511(17) .
C13 C14 1.490(2) .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
