Dearomatization Approach to 2-Trifluoromethylated Benzofuran and Dihydrobenzofuran Products.
Smith, David T.; Vitaku, Edon; Njardarson, Jon T.; Organic letters 19 (2017) 3508–3511; doi:10.1021/acs.orglett.7b01479

data_1546608
_publ_section_title
;
 Dearomatization Approach to 2-Trifluoromethylated Benzofuran and
 Dihydrobenzofuran Products.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              3508
_journal_page_last               3511
_journal_paper_doi               10.1021/acs.orglett.7b01479
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C12 H8 F6 O3'
_chemical_formula_sum            'C12 H8 F6 O3'
_chemical_formula_weight         314.18
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-05-10
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                75.537(5)
_cell_angle_beta                 83.093(5)
_cell_angle_gamma                78.250(5)
_cell_formula_units_Z            2
_cell_length_a                   4.9314(6)
_cell_length_b                   9.4371(11)
_cell_length_c                   13.4664(15)
_cell_measurement_reflns_used    4958
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.22
_cell_measurement_theta_min      2.27
_cell_volume                     592.53(12)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0233
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            10172
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.261
_diffrn_reflns_theta_min         1.566
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0773 before and 0.0467 after correction. The Ratio of minimum to maximum transmission is 0.8145. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.761
_exptl_crystal_description       block
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.416
_exptl_crystal_size_mid          0.148
_exptl_crystal_size_min          0.069
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2374
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.057
_refine_ls_R_factor_all          0.0374
_refine_ls_R_factor_gt           0.0316
_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^)+(0.0472P)^2^+0.1773P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0852
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2060
_reflns_number_total             2374
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol7b01479_si_003.cif
_cod_data_source_block           mo_dts_195_0m
_cod_depositor_comments
'Adding full bibliography for 1546607--1546608.cif.'
_cod_database_code               1546608
_shelxl_version_number           2012-9
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'