Access to Perfluoroalkyl-Substituted Enones and Indolin-2-ones via Multicomponent Pd-Catalyzed Carbonylative Reactions.
Yin, Hongfei; Skrydstrup, Troels; The Journal of organic chemistry 82 (2017) 6474–6481; doi:10.1021/acs.joc.7b00942

data_4032564
_publ_section_title
;
 Access to Perfluoroalkyl-Substituted Enones and Indolin-2-ones via
 Multicomponent Pd-Catalyzed Carbonylative Reactions.
;
_journal_issue                   12
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              6474
_journal_page_last               6481
_journal_paper_doi               10.1021/acs.joc.7b00942
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C13 H6 F9 N O'
_chemical_formula_sum            'C13 H6 F9 N O'
_chemical_formula_weight         363.19
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-03-12
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.829(13)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   14.847(19)
_cell_length_b                   5.161(7)
_cell_length_c                   51.87(7)
_cell_measurement_reflns_used    901
_cell_measurement_temperature    100
_cell_measurement_theta_max      17.610
_cell_measurement_theta_min      2.280
_cell_volume                     3973(9)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker Apex2'
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56086
_diffrn_reflns_av_R_equivalents  0.1579
_diffrn_reflns_av_unetI/netI     0.2207
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       57
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_number            17788
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        18.154
_diffrn_reflns_theta_max         18.154
_diffrn_reflns_theta_min         1.117
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.6657
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.2026 before and 0.0720 after correction. The Ratio of minimum to maximum transmission is 0.6657. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.822
_exptl_crystal_description       irregular
_exptl_crystal_F_000             2160
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.100
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     649
_refine_ls_number_reflns         5699
_refine_ls_number_restraints     603
_refine_ls_restrained_S_all      0.957
_refine_ls_R_factor_all          0.1596
_refine_ls_R_factor_gt           0.0911
_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^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2177
_refine_ls_wR_factor_ref         0.2684
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3034
_reflns_number_total             5699
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00942_si_003.cif
_cod_data_source_block           2017_03_03_0m
_cod_depositor_comments          'Adding full bibliography for 4032564.cif.'
_cod_database_code               4032564
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3.a Aromatic/amide H refined with riding coordinates:
 N1B(H1B), N1A(H1A), N1(H1), C8B(H8B), C9A(H9A), C9B(H9B), C8(H8), C6(H6),
 C7(H7), C5A(H5A), C6A(H6A), C6B(H6B), C9(H9), C5B(H5B), C8A(H8A), C7B(H7B),
 C5(H5), C7A(H7A)
;
_olex2_submission_special_instructions 'No special instructions were received'