Chemoselective Mono- and Difluorination of 1,3-Dicarbonyl Compounds.
Tang, Lin; Yang, Zhen; Jiao, Jingchao; Cui, Ying; Zou, Guodong; Zhou, Qiuju; Zhou, Yuqiang; Rao, Weihao; Ma, Xiantao; The Journal of organic chemistry 84 (2019) 10449–10458; doi:10.1021/acs.joc.9b01808

data_4034036
_publ_section_title
;
 Chemoselective Mono- and Difluorination of 1,3-Dicarbonyl Compounds.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10449
_journal_page_last               10458
_journal_paper_doi               10.1021/acs.joc.9b01808
_journal_volume                  84
_journal_year                    2019
_chemical_formula_moiety         'C10 H8 Cl F2 N O2'
_chemical_formula_sum            'C10 H8 Cl F2 N O2'
_chemical_formula_weight         247.62
_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
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 98.818(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.454(2)
_cell_length_b                   9.9349(19)
_cell_length_c                   9.8667(17)
_cell_measurement_reflns_used    6390
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      26.27
_cell_measurement_theta_min      2.73
_cell_volume                     1109.5(3)
_computing_cell_refinement       'APEX3 (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'APEX3 (Bruker, 2016)'
_computing_molecular_graphics    'DIAMOND. Version 3.2k. Crystal Impact'
_computing_publication_material  'Windows Word 2010'
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_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 QUEST ECO'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11953
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_min         2.728
_exptl_absorpt_coefficient_mu    0.355
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2168
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0544
_refine_ls_R_factor_gt           0.0468
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0787P)^2^+0.4432P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1357
_refine_ls_wR_factor_ref         0.1452
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1836
_reflns_number_total             2168
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b01808_si_003.cif
_cod_data_source_block           3h
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4034036
_shelx_shelxl_version_number     2016/6
_shelx_res_checksum              64133
_shelx_hkl_checksum              53104