Visible-light-initiated external photocatalyst-free synthesis of α,α-difluoro-β-ketoamides from 4-aminocoumarins.
Li, Ningbo; Wang, Yuxin; Gu, Shuo; Hu, Chuqian; Yang, Qian; Jin, Zhaohui; Ouyang, Wen-Tao; Qiao, Jie; He, Wei-Min; Organic & biomolecular chemistry 21 (2023) 370–374; doi:10.1039/d2ob01914k

data_7159027
_publ_section_title
;
 Visible-light-initiated external photocatalyst-free synthesis of
 &#x3b1;,&#x3b1;-difluoro-&#x3b2;-ketoamides from 4-aminocoumarins.
;
_journal_issue                   2
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              370
_journal_page_last               374
_journal_paper_doi               10.1039/d2ob01914k
_journal_volume                  21
_journal_year                    2023
_chemical_formula_moiety         'C16 H13 F2 N O3'
_chemical_formula_sum            'C16 H13 F2 N O3'
_chemical_formula_weight         305.27
_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     iterative
_audit_creation_date             2021-07-27
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-05-31 deposited with the CCDC.	2022-12-01 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.944(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.0257(15)
_cell_length_b                   17.525(5)
_cell_length_c                   16.304(5)
_cell_measurement_reflns_used    4992
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      21.514
_cell_measurement_theta_min      3.416
_cell_volume                     1434.1(7)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1184
_diffrn_reflns_av_unetI/netI     0.0923
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            30190
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.813
_diffrn_reflns_theta_min         3.416
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7017
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1358 before and 0.0641 after correction.
The Ratio of minimum to maximum transmission is 0.9411.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.177
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3368
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.1844
_refine_ls_R_factor_gt           0.0630
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0647P)^2^+0.2026P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1172
_refine_ls_wR_factor_ref         0.1520
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1549
_reflns_number_total             3368
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob01914k2.cif
_cod_data_source_block           111
_cod_depositor_comments          'Adding full bibliography for 7159027.cif.'
_cod_database_code               7159027
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.960
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C6(H6), C7(H7), C3(H3), C16(H16), C14(H14), C12(H12), C13(H13),
 C15(H15)
2.b Idealised Me refined as rotating group:
 C1(H1B,H1C,H1D)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1A)
;
_shelx_res_checksum              49215
_olex2_submission_special_instructions 'No special instructions were received'