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#$Date: 2022-05-03 11:15:20 +0300 (Tue, 03 May 2022) $
#$Revision: 274838 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/51/8105108.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_8105108
loop_
_publ_author_name
'Guo, You-Yuan'
'Wang, Huan'
'Ma, Xin'
'Fu, Ying'
_publ_section_title
;
 Crystal structure of 5,5-dimethyl-3-oxocyclohex-1-en-1-yl
 4-(2,2-dichloroacetyl)-3,4-dihydro-2
 H-benzo[b][1,4]oxazine-7-carboxylate, C19H19Cl2NO5
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              361
_journal_page_last               363
_journal_paper_doi               10.1515/ncrs-2019-0671
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C19 H19 Cl2 N O5'
_chemical_formula_sum            'C19 H19 Cl2 N O5'
_chemical_formula_weight         412.25
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   12.6750(18)
_cell_length_b                   11.0927(17)
_cell_length_c                   28.400(4)
_cell_measurement_reflns_used    9936
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.13
_cell_measurement_theta_min      2.83
_cell_volume                     3993.0(10)
_computing_cell_refinement       'Bruker D8 Venture'
_computing_data_collection       'Bruker D8 Venture'
_computing_data_reduction        'Bruker D8 Venture'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXT-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'D8 VENTURE PHOTON II'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_av_sigmaI/netI    0.0439
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            35421
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.397
_diffrn_reflns_theta_min         2.831
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.354
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_correction_T_min  0.949
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_description       block
_exptl_crystal_F_000             1712
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     246
_refine_ls_number_reflns         4974
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.1227
_refine_ls_R_factor_gt           0.0700
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
'w=1/[σ²(Fo²)+(0.0652P)²+4.1453P] where P=(Fo²+2Fc²)/3'
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1704
_refine_ls_wR_factor_ref         0.2011
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2812
_reflns_number_total             4974
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0671_suppl.cif
_cod_data_source_block           1
_cod_database_code               8105108
_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.
;
_shelx_estimated_absorpt_t_min   0.949
_shelx_estimated_absorpt_t_max   0.965
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7004(3) 1.1364(4) 0.09129(13) 0.0689(10) Uani 1 1 d . . . . .
H1 H 0.6566 1.1895 0.1108 0.083 Uiso 1 1 calc R U . . .
C2 C 0.7438(3) 1.0328(3) 0.12162(12) 0.0622(9) Uani 1 1 d . . . . .
C3 C 0.5632(3) 1.0163(3) 0.15892(13) 0.0626(9) Uani 1 1 d . . . . .
H3A H 0.5450 1.0812 0.1375 0.075 Uiso 1 1 calc R U . . .
H3B H 0.5486 1.0429 0.1908 0.075 Uiso 1 1 calc R U . . .
C4 C 0.4995(3) 0.9079(3) 0.14788(13) 0.0632(9) Uani 1 1 d . . . . .
H4A H 0.4252 0.9276 0.1502 0.076 Uiso 1 1 calc R U . . .
H4B H 0.5137 0.8827 0.1158 0.076 Uiso 1 1 calc R U . . .
C5 C 0.6247(2) 0.8044(3) 0.19542(11) 0.0488(7) Uani 1 1 d . . . . .
C6 C 0.7045(2) 0.8858(3) 0.18279(10) 0.0466(7) Uani 1 1 d . . . . .
C7 C 0.8047(2) 0.8701(3) 0.20146(12) 0.0552(8) Uani 1 1 d . . . . .
H7 H 0.8586 0.9226 0.1928 0.066 Uiso 1 1 calc R U . . .
C8 C 0.8253(2) 0.7782(3) 0.23246(11) 0.0529(8) Uani 1 1 d . . . . .
H8 H 0.8929 0.7688 0.2447 0.063 Uiso 1 1 calc R U . . .
C9 C 0.7457(2) 0.6995(3) 0.24560(10) 0.0482(7) Uani 1 1 d . . . . .
C10 C 0.6457(2) 0.7122(3) 0.22676(11) 0.0526(8) Uani 1 1 d . . . . .
H10 H 0.5925 0.6587 0.2352 0.063 Uiso 1 1 calc R U . . .
C11 C 0.7598(3) 0.6060(3) 0.28245(11) 0.0550(8) Uani 1 1 d . . . . .
C12 C 0.8802(2) 0.5307(3) 0.33723(11) 0.0509(8) Uani 1 1 d . . . . .
C13 C 0.9125(3) 0.4178(4) 0.33704(13) 0.0691(10) Uani 1 1 d . . . . .
H13 H 0.9198 0.3769 0.3087 0.083 Uiso 1 1 calc R U . . .
C14 C 0.9366(4) 0.3570(4) 0.38123(16) 0.0835(13) Uani 1 1 d . . . . .
C15 C 0.9331(3) 0.4297(4) 0.42524(13) 0.0702(10) Uani 1 1 d . . . . .
H15A H 1.0018 0.4659 0.4303 0.084 Uiso 1 1 calc R U . . .
H15B H 0.9190 0.3764 0.4516 0.084 Uiso 1 1 calc R U . . .
C16 C 0.8505(3) 0.5285(3) 0.42455(12) 0.0580(8) Uani 1 1 d . . . . .
C17 C 0.8672(3) 0.6037(3) 0.38008(12) 0.0650(9) Uani 1 1 d . . . . .
H17A H 0.8072 0.6570 0.3760 0.078 Uiso 1 1 calc R U . . .
H17B H 0.9294 0.6535 0.3842 0.078 Uiso 1 1 calc R U . . .
C18 C 0.8626(5) 0.6085(5) 0.46788(16) 0.1056(17) Uani 1 1 d . . . . .
H18A H 0.9321 0.6428 0.4683 0.158 Uiso 1 1 calc R U . . .
H18B H 0.8521 0.5611 0.4958 0.158 Uiso 1 1 calc R U . . .
H18C H 0.8111 0.6719 0.4668 0.158 Uiso 1 1 calc R U . . .
C19 C 0.7407(3) 0.4741(5) 0.42446(15) 0.0827(13) Uani 1 1 d . . . . .
H19A H 0.6892 0.5374 0.4228 0.124 Uiso 1 1 calc R U . . .
H19B H 0.7303 0.4286 0.4528 0.124 Uiso 1 1 calc R U . . .
H19C H 0.7331 0.4219 0.3977 0.124 Uiso 1 1 calc R U . . .
Cl1 Cl 0.80420(11) 1.21969(12) 0.06655(5) 0.1024(5) Uani 1 1 d . . . . .
Cl2 Cl 0.62195(10) 1.07126(13) 0.04608(4) 0.0920(4) Uani 1 1 d . . . . .
N1 N 0.67630(19) 0.9859(3) 0.15407(9) 0.0524(7) Uani 1 1 d . . . . .
O1 O 0.8318(2) 0.9969(3) 0.11574(11) 0.0948(11) Uani 1 1 d . . . . .
O2 O 0.52355(16) 0.8104(2) 0.17957(9) 0.0680(7) Uani 1 1 d . . . . .
O3 O 0.6905(2) 0.5503(3) 0.30061(10) 0.0808(9) Uani 1 1 d . . . . .
O4 O 0.86288(17) 0.5906(2) 0.29452(8) 0.0621(7) Uani 1 1 d . . . . .
O5 O 0.9617(4) 0.2522(3) 0.38214(15) 0.1489(19) 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'
Cl Cl 0.1484 0.1585 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C1 Cl1 110.4(3) . .
C2 C1 Cl2 107.5(3) . .
Cl1 C1 Cl2 110.1(2) . .
C2 C1 H1 109.6 . .
Cl1 C1 H1 109.6 . .
Cl2 C1 H1 109.6 . .
O1 C2 N1 123.6(3) . .
O1 C2 C1 120.3(3) . .
N1 C2 C1 116.1(3) . .
N1 C3 C4 108.8(3) . .
N1 C3 H3A 109.9 . .
C4 C3 H3A 109.9 . .
N1 C3 H3B 109.9 . .
C4 C3 H3B 109.9 . .
H3A C3 H3B 108.3 . .
O2 C4 C3 111.3(3) . .
O2 C4 H4A 109.4 . .
C3 C4 H4A 109.4 . .
O2 C4 H4B 109.4 . .
C3 C4 H4B 109.4 . .
H4A C4 H4B 108.0 . .
O2 C5 C10 115.5(3) . .
O2 C5 C6 124.3(3) . .
C10 C5 C6 120.2(3) . .
C7 C6 C5 118.8(3) . .
C7 C6 N1 123.1(3) . .
C5 C6 N1 117.9(3) . .
C8 C7 C6 120.9(3) . .
C8 C7 H7 119.6 . .
C6 C7 H7 119.6 . .
C7 C8 C9 120.1(3) . .
C7 C8 H8 119.9 . .
C9 C8 H8 119.9 . .
C10 C9 C8 119.9(3) . .
C10 C9 C11 117.0(3) . .
C8 C9 C11 122.9(3) . .
C5 C10 C9 120.1(3) . .
C5 C10 H10 120.0 . .
C9 C10 H10 120.0 . .
O3 C11 O4 122.2(3) . .
O3 C11 C9 125.4(3) . .
O4 C11 C9 112.4(3) . .
C13 C12 O4 119.7(3) . .
C13 C12 C17 124.1(3) . .
O4 C12 C17 116.0(3) . .
C12 C13 C14 120.1(4) . .
C12 C13 H13 120.0 . .
C14 C13 H13 120.0 . .
O5 C14 C13 121.3(4) . .
O5 C14 C15 120.8(4) . .
C13 C14 C15 117.8(3) . .
C14 C15 C16 113.7(3) . .
C14 C15 H15A 108.8 . .
C16 C15 H15A 108.8 . .
C14 C15 H15B 108.8 . .
C16 C15 H15B 108.8 . .
H15A C15 H15B 107.7 . .
C15 C16 C18 109.9(3) . .
C15 C16 C19 110.3(3) . .
C18 C16 C19 109.0(4) . .
C15 C16 C17 108.0(3) . .
C18 C16 C17 109.6(3) . .
C19 C16 C17 110.1(3) . .
C12 C17 C16 113.5(3) . .
C12 C17 H17A 108.9 . .
C16 C17 H17A 108.9 . .
C12 C17 H17B 108.9 . .
C16 C17 H17B 108.9 . .
H17A C17 H17B 107.7 . .
C16 C18 H18A 109.5 . .
C16 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
C16 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C16 C19 H19A 109.5 . .
C16 C19 H19B 109.5 . .
H19A C19 H19B 109.5 . .
C16 C19 H19C 109.5 . .
H19A C19 H19C 109.5 . .
H19B C19 H19C 109.5 . .
C2 N1 C6 121.9(3) . .
C2 N1 C3 125.8(3) . .
C6 N1 C3 111.6(3) . .
C5 O2 C4 116.3(3) . .
C11 O4 C12 115.3(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.539(5) .
C1 Cl1 1.755(4) .
C1 Cl2 1.777(4) .
C1 H1 0.9800 .
C2 O1 1.195(4) .
C2 N1 1.361(4) .
C3 N1 1.479(4) .
C3 C4 1.482(5) .
C3 H3A 0.9700 .
C3 H3B 0.9700 .
C4 O2 1.439(4) .
C4 H4A 0.9700 .
C4 H4B 0.9700 .
C5 O2 1.361(3) .
C5 C10 1.382(4) .
C5 C6 1.402(4) .
C6 C7 1.387(4) .
C6 N1 1.424(4) .
C7 C8 1.372(5) .
C7 H7 0.9300 .
C8 C9 1.386(4) .
C8 H8 0.9300 .
C9 C10 1.383(4) .
C9 C11 1.483(4) .
C10 H10 0.9300 .
C11 O3 1.192(4) .
C11 O4 1.362(4) .
C12 C13 1.318(5) .
C12 O4 1.400(4) .
C12 C17 1.471(5) .
C13 C14 1.457(6) .
C13 H13 0.9300 .
C14 O5 1.206(5) .
C14 C15 1.488(6) .
C15 C16 1.516(5) .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C16 C18 1.525(6) .
C16 C19 1.516(5) .
C16 C17 1.528(5) .
C17 H17A 0.9700 .
C17 H17B 0.9700 .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
C19 H19A 0.9600 .
C19 H19B 0.9600 .
C19 H19C 0.9600 .
