#------------------------------------------------------------------------------
#$Date: 2025-08-18 17:33:07 +0200 (Mon 18 de Aug de 2025) $
#$Revision: 301779 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/53/1545396.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_1545396
loop_
_publ_author_name
'Song, Ping'
'Yu, Peng'
'Lin, Jin-Shun'
'Li, Yiqun'
'Yang, Ning-Yuan'
'Liu, Xin-Yuan'
_publ_section_title
;
 Transition-Metal-Free β-C-H Bond Carbonylation of Enamides or Amides
 with a Trifluoromethyl Group as CO Surrogate for the Synthesis of
 1,3-Oxazin-6-ones.
;
_journal_issue                   6
_journal_name_full               'Organic letters'
_journal_page_first              1330
_journal_page_last               1333
_journal_paper_doi               10.1021/acs.orglett.7b00178
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C16 H10 Cl N O2'
_chemical_formula_sum            'C16 H10 Cl N O2'
_chemical_formula_weight         283.70
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-03-06
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2016.02.24 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                78.039(2)
_cell_angle_beta                 87.320(2)
_cell_angle_gamma                63.031(2)
_cell_formula_units_Z            2
_cell_length_a                   7.4540(4)
_cell_length_b                   7.9852(4)
_cell_length_c                   12.3366(6)
_cell_measurement_reflns_used    2007
_cell_measurement_temperature    100
_cell_measurement_theta_max      65.87
_cell_measurement_theta_min      3.67
_cell_volume                     639.29(6)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0298
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9262
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        67.327
_diffrn_reflns_theta_max         67.327
_diffrn_reflns_theta_min         3.668
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.649
_exptl_absorpt_correction_T_max  0.7529
_exptl_absorpt_correction_T_min  0.5818
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0675 before and 0.0484 after correction. The Ratio of minimum to maximum transmission is 0.7727. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.474
_exptl_crystal_description       block
_exptl_crystal_F_000             292
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.296
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2238
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0303
_refine_ls_R_factor_gt           0.0301
_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)+(0.0349P)²+0.3323P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0764
_refine_ls_wR_factor_ref         0.0766
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2227
_reflns_number_total             2238
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ol7b00178_si_003.cif
_cod_data_source_block           cxy372_0m
_cod_depositor_comments
'Adding full bibliography for 1545396--1545397.cif.'
_cod_original_cell_volume        639.30(6)
_cod_database_code               1545396
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C12(H12), C13(H13), C14(H14),
 C15(H15), C16(H16)
;
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -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
Cl1 Cl 0.77166(5) 0.51548(4) 0.03573(2) 0.01981(13) Uani 1 1 d .
O1 O 0.69305(14) 0.37897(13) 0.26156(7) 0.0158(2) Uani 1 1 d .
O2 O 0.88463(16) 0.06833(13) 0.32910(8) 0.0223(2) Uani 1 1 d .
N1 N 0.62235(16) 0.61660(15) 0.36404(9) 0.0140(2) Uani 1 1 d .
C1 C 0.5421(2) 0.69249(19) 0.06623(11) 0.0154(3) Uani 1 1 d .
C2 C 0.4194(2) 0.8288(2) -0.02291(11) 0.0189(3) Uani 1 1 d .
H2 H 0.4577 0.8185 -0.0967 0.023 Uiso 1 1 calc R
C3 C 0.2410(2) 0.9799(2) -0.00375(12) 0.0205(3) Uani 1 1 d .
H3 H 0.1565 1.0733 -0.0646 0.025 Uiso 1 1 calc R
C4 C 0.1847(2) 0.99572(19) 0.10404(12) 0.0198(3) Uani 1 1 d .
H4 H 0.0620 1.0996 0.1169 0.024 Uiso 1 1 calc R
C5 C 0.3078(2) 0.85974(19) 0.19262(11) 0.0169(3) Uani 1 1 d .
H5 H 0.2694 0.8720 0.2662 0.020 Uiso 1 1 calc R
C6 C 0.4883(2) 0.70423(18) 0.17557(11) 0.0140(3) Uani 1 1 d .
C7 C 0.60816(19) 0.56352(18) 0.27506(11) 0.0132(3) Uani 1 1 d .
C8 C 0.8114(2) 0.22832(19) 0.34814(11) 0.0163(3) Uani 1 1 d .
C9 C 0.8286(2) 0.28525(19) 0.44800(11) 0.0167(3) Uani 1 1 d .
H9 H 0.9043 0.1904 0.5108 0.020 Uiso 1 1 calc R
C10 C 0.73763(19) 0.47361(18) 0.45399(10) 0.0140(3) Uani 1 1 d .
C11 C 0.7549(2) 0.54198(19) 0.55390(11) 0.0142(3) Uani 1 1 d .
C12 C 0.8914(2) 0.41739(19) 0.64269(11) 0.0163(3) Uani 1 1 d .
H12 H 0.9749 0.2870 0.6391 0.020 Uiso 1 1 calc R
C13 C 0.9054(2) 0.4832(2) 0.73565(11) 0.0184(3) Uani 1 1 d .
H13 H 0.9976 0.3973 0.7958 0.022 Uiso 1 1 calc R
C14 C 0.7856(2) 0.6741(2) 0.74174(11) 0.0188(3) Uani 1 1 d .
H14 H 0.7966 0.7188 0.8055 0.023 Uiso 1 1 calc R
C15 C 0.6499(2) 0.7990(2) 0.65426(12) 0.0202(3) Uani 1 1 d .
H15 H 0.5675 0.9295 0.6582 0.024 Uiso 1 1 calc R
C16 C 0.6344(2) 0.73389(19) 0.56086(11) 0.0177(3) Uani 1 1 d .
H16 H 0.5412 0.8202 0.5012 0.021 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C7 O1 C8 120.26(10)
C7 N1 C10 117.41(11)
C2 C1 Cl1 116.91(10)
C2 C1 C6 121.18(12)
C6 C1 Cl1 121.81(10)
C1 C2 H2 120.2
C3 C2 C1 119.65(13)
C3 C2 H2 120.2
C2 C3 H3 119.8
C2 C3 C4 120.33(12)
C4 C3 H3 119.8
C3 C4 H4 120.1
C5 C4 C3 119.81(13)
C5 C4 H4 120.1
C4 C5 H5 119.5
C4 C5 C6 121.05(12)
C6 C5 H5 119.5
C1 C6 C5 117.97(12)
C1 C6 C7 124.67(12)
C5 C6 C7 117.36(12)
O1 C7 C6 113.16(11)
N1 C7 O1 125.40(12)
N1 C7 C6 121.42(11)
O1 C8 C9 114.99(11)
O2 C8 O1 116.34(12)
O2 C8 C9 128.67(13)
C8 C9 H9 119.7
C10 C9 C8 120.62(12)
C10 C9 H9 119.7
N1 C10 C11 115.56(11)
C9 C10 N1 121.30(12)
C9 C10 C11 123.14(12)
C12 C11 C10 120.99(12)
C12 C11 C16 118.79(12)
C16 C11 C10 120.22(12)
C11 C12 H12 119.8
C13 C12 C11 120.33(12)
C13 C12 H12 119.8
C12 C13 H13 119.7
C12 C13 C14 120.51(13)
C14 C13 H13 119.7
C13 C14 H14 120.1
C15 C14 C13 119.71(13)
C15 C14 H14 120.1
C14 C15 H15 119.9
C14 C15 C16 120.13(13)
C16 C15 H15 119.9
C11 C16 H16 119.7
C15 C16 C11 120.53(13)
C15 C16 H16 119.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C1 1.7418(13)
O1 C7 1.3586(16)
O1 C8 1.3999(16)
O2 C8 1.2104(17)
N1 C7 1.2807(17)
N1 C10 1.3956(17)
C1 C2 1.3879(19)
C1 C6 1.3989(19)
C2 H2 0.9500
C2 C3 1.383(2)
C3 H3 0.9500
C3 C4 1.389(2)
C4 H4 0.9500
C4 C5 1.3833(19)
C5 H5 0.9500
C5 C6 1.4009(19)
C6 C7 1.4791(18)
C8 C9 1.4283(19)
C9 H9 0.9500
C9 C10 1.3580(19)
C10 C11 1.4803(18)
C11 C12 1.3998(19)
C11 C16 1.4005(19)
C12 H12 0.9500
C12 C13 1.3830(19)
C13 H13 0.9500
C13 C14 1.391(2)
C14 H14 0.9500
C14 C15 1.387(2)
C15 H15 0.9500
C15 C16 1.388(2)
C16 H16 0.9500
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 132608137
