Base-Mediated Tunable Synthesis of 2-Trifluoromethylated Furans and Dihydrofuranols: Extraordinary Stable in Sulfuric Acid.
Wang, Junwen; Chen, Shouxiong; Wu, Wei; Wen, Shunli; Weng, Zhiqiang; The Journal of organic chemistry  (2019) –; doi:10.1021/acs.joc.9b02326

data_4036062
_publ_section_title
;
 Base-Mediated Tunable Synthesis of 2-Trifluoromethylated Furans and
 Dihydrofuranols: Extraordinary Stable in Sulfuric Acid.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b02326
_journal_year                    2019
_chemical_formula_moiety         'C12 H8 F3 N O2'
_chemical_formula_sum            'C12 H8 F3 N O2'
_chemical_formula_weight         255.19
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     iterative
_audit_creation_date             2019-05-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 98.823(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.0213(16)
_cell_length_b                   8.5573(13)
_cell_length_c                   25.048(4)
_cell_measurement_reflns_used    3218
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.003
_cell_measurement_theta_min      2.518
_cell_volume                     2334.4(6)
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            13797
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.675
_diffrn_reflns_theta_min         1.870
_exptl_absorpt_coefficient_mu    0.131
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6919
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.95
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.065
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.120
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         5365
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.072
_refine_ls_R_factor_all          0.1159
_refine_ls_R_factor_gt           0.0623
_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^)+(0.0848P)^2^+0.2248P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1427
_refine_ls_wR_factor_ref         0.1754
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3108
_reflns_number_total             5365
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02326_si_002.cif
_cod_data_source_block           123
_cod_depositor_comments
;

2020-04-07
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C24 H16 F6 N2 O4'
_cod_original_formula_weight         510.39
_cod_original_formula_moiety         '2(C12 H8 F3 N O2)'
_cod_original_formula_units_Z            4
_cod_database_code               4036062
_shelxl_version_number           2013-2
_olex2_refinement_description
;
;
_shelx_res_checksum              86179
_shelx_hkl_checksum              18161
_olex2_submission_special_instructions 'No special instructions were received'