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_4032753
_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         'C17 H9 F9 O S'
_chemical_formula_sum            'C17 H9 F9 O S'
_chemical_formula_weight         432.30
_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
_atom_sites_solution_primary     dual
_audit_creation_date             2017-03-11
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_cell_angle_alpha                90
_cell_angle_beta                 92.372(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.0387(6)
_cell_length_b                   5.8212(3)
_cell_length_c                   22.0905(12)
_cell_measurement_reflns_used    5876
_cell_measurement_temperature    100
_cell_measurement_theta_max      23.607
_cell_measurement_theta_min      2.464
_cell_volume                     1675.25(15)
_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  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           AgK\a
_diffrn_radiation_wavelength     0.56086
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            18125
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        19.665
_diffrn_reflns_theta_max         23.688
_diffrn_reflns_theta_min         1.456
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9502
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1036 before and 0.0416 after correction. The Ratio of minimum to maximum transmission is 0.9502. 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    1.714
_exptl_crystal_description       irregular
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         5116
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0382
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0352P)^2^+1.0755P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0881
_refine_ls_wR_factor_ref         0.0960
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4076
_reflns_number_total             5116
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00942_si_002.cif
_cod_data_source_block           2017_03_11_0m
_cod_database_code               4032753
_shelx_shelxl_version_number     2014/7
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00E(H00E), C00F(H00F), C00H(H00H), C00I(H00I), C00K(H00K), C00L(H00L),
 C00N(H00N), C00O(H00O), C00Q(H00Q)
;
_olex2_submission_special_instructions 'No special instructions were received'