Selective Metal-Controlled Synthesis of Trifluoromethylated (Indolin-2-ylidene)methyl- and Quinolin-3-ylphosphonates.
Mitrofanov, Alexander; Bychkova, Valentina A.; Nefedov, Sergey E.; Beletskaya, Irina P.; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00913

data_4038557
_publ_section_title
;
 Selective Metal-Controlled Synthesis of Trifluoromethylated
 (Indolin-2-ylidene)methyl- and Quinolin-3-ylphosphonates.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00913
_journal_year                    2020
_chemical_formula_sum            'C14 H16 Cl F3 N O4 P'
_chemical_formula_weight         385.70
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 105.5990(10)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.7704(4)
_cell_length_b                   15.6900(5)
_cell_length_c                   18.6268(6)
_cell_measurement_reflns_used    7054
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.50
_cell_measurement_theta_min      2.60
_cell_volume                     3313.25(19)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            19990
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_min         2.216
_exptl_absorpt_coefficient_mu    0.377
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_description       needls
_exptl_crystal_F_000             1584
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.612
_refine_diff_density_min         -0.558
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         4818
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.0895
_refine_ls_R_factor_gt           0.0714
_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/[\s^2^(Fo^2^)+(0.0992P)^2^+12.8473P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1991
_refine_ls_wR_factor_ref         0.2109
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3826
_reflns_number_total             4818
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00913_si_001.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'I 2/a'
_cod_database_code               4038557
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.912
_shelx_estimated_absorpt_t_max   0.970
_shelx_res_checksum              8162
_shelx_hkl_checksum              65400