Tunable regiodivergent phosphine-catalyzed [3 + 2] cycloaddition of alkynones and trifluoroacetyl phenylamides
Sun, Yao-Liang; Wei, Yin; Shi, Min; Organic Chemistry Frontiers 4 (2017) 2392–; doi:10.1039/C7QO00512A

data_1553833
_publ_section_title
;
 Tunable regiodivergent phosphine-catalyzed [3 + 2] cycloaddition of
 alkynones and trifluoroacetyl phenylamides
;
_journal_issue                   12
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2392
_journal_paper_doi               10.1039/C7QO00512A
_journal_volume                  4
_journal_year                    2017
_chemical_formula_sum            'C23 H19 Cl F3 N O5'
_chemical_formula_weight         481.84
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2016-12-07 deposited with the CCDC.
2017-08-29 downloaded from the CCDC.
;
_cell_angle_alpha                88.853(3)
_cell_angle_beta                 83.694(3)
_cell_angle_gamma                77.708(3)
_cell_formula_units_Z            2
_cell_length_a                   7.3052(11)
_cell_length_b                   10.5757(16)
_cell_length_c                   14.449(2)
_cell_measurement_reflns_used    1798
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      46.217
_cell_measurement_theta_min      4.848
_cell_volume                     1084.1(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6268
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         1.971
_exptl_absorpt_coefficient_mu    0.238
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     304
_refine_ls_number_reflns         4012
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0465
_refine_ls_shift/su_max          0.022
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0595P)^2^+0.1782P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1114
_refine_ls_wR_factor_ref         0.1227
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3024
_reflns_number_total             4012
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00512a2.cif
_cod_data_source_block           cd16720
_cod_database_code               1553833
_shelx_estimated_absorpt_t_min   0.954
_shelx_estimated_absorpt_t_max   0.972
_shelxl_version_number           2013-4
_shelx_res_checksum              68687
_shelx_hkl_checksum              13257