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_1546607
_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         'C10 H9 F3 O3'
_chemical_formula_sum            'C10 H9 F3 O3'
_chemical_formula_weight         234.18
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_date             2017-05-11
_audit_creation_method
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.6310(4)
_cell_length_b                   8.0161(4)
_cell_length_c                   16.2346(9)
_cell_measurement_reflns_used    5799
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.30
_cell_measurement_theta_min      2.51
_cell_volume                     993.08(9)
_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  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 0.9985
_diffrn_measured_fraction_theta_max 0.9985
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_unetI/netI     0.0164
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            10142
_diffrn_reflns_theta_full        26.3683
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         2.51
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6610
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.0559 before and 0.0406 after correction. The Ratio of minimum to maximum transmission is 0.8868. The \l/2 correction factor is 0.0015.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
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_exptl_crystal_description       block
_exptl_crystal_F_000             480.4437
_exptl_crystal_size_max          0.402
_exptl_crystal_size_mid          0.397
_exptl_crystal_size_min          0.207
_refine_diff_density_max         0.1824
_refine_diff_density_min         -0.2180
_refine_diff_density_rms         0.0396
_refine_ls_abs_structure_details
'Flack, H. D. (1983). Acta Cryst. A39, 876-881.'
_refine_ls_abs_structure_Flack   0.2(8)
_refine_ls_d_res_high            0.8001
_refine_ls_d_res_low             8.1173
_refine_ls_goodness_of_fit_ref   1.1017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    15
_refine_ls_number_parameters     146
_refine_ls_number_reflns         2033
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.1017
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0284
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0351P)^2^+0.2862P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0724
_refine_ls_wR_factor_ref         0.0744
_reflns_Friedel_coverage         0.998
_reflns_limit_h_max              9
_reflns_limit_h_min              -9
_reflns_limit_k_max              10
_reflns_limit_k_min              -9
_reflns_limit_l_max              20
_reflns_limit_l_min              -20
_reflns_number_gt                1979
_reflns_number_total             2033
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            ol7b01479_si_001.cif
_cod_data_source_block           mo_dts_193_chiral_1_0m
_cod_depositor_comments
'Adding full bibliography for 1546607--1546608.cif.'
_cod_original_sg_symbol_Hall     ' P 2ac 2ab'
_cod_database_code               1546607
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C5(H5)
2.c Idealised Me refined as rotating group:
 C10(H10a,H10b,H10c)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'