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_4036060
_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 H9 F3 N2 O'
_chemical_formula_weight         254.21
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-06-17
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 100.496(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.7852(8)
_cell_length_b                   7.4546(5)
_cell_length_c                   13.3425(8)
_cell_measurement_reflns_used    1661
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.7590
_cell_measurement_theta_min      3.3620
_cell_volume                     1152.58(13)
_computing_cell_refinement       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.35c (Rigaku OD, 2017)'
_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    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.1281
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -88.00 -50.00   1.00    1.00    --  -33.50 -37.00-180.00   38
  2  \w     -3.00  25.00   1.00    1.00    --   35.87 -99.00 -90.00   28
  3  \w     -1.00  31.00   1.00    1.00    --   35.87 -37.00 -30.00   32
  4  \w     20.00  52.00   1.00    1.00    --   35.87  19.00   0.00   32
  5  \w     71.00  99.00   1.00    1.00    --   35.87 178.00 -60.00   28
  6  \w     40.00  74.00   1.00    1.00    --   35.87 -99.00 -90.00   34
  7  \w     74.00 107.00   1.00    1.00    --   35.87  19.00   0.00   33
  8  \w     63.00  91.00   1.00    1.00    --   35.87 178.00 120.00   28
  9  \w     61.00 108.00   1.00    1.00    --   35.87-178.00 -90.00   47
 10  \w     68.00 102.00   1.00    1.00    --   35.87 178.00-180.00   34
 11  \w     64.00 107.00   1.00    1.00    --   35.87-178.00  60.00   43
 12  \w     90.00 153.00   1.00    1.00    --  108.00  61.00 150.00   63
 13  \w     42.00  71.00   1.00    1.00    --  108.00 -77.00-120.00   29
 14  \w     75.00 118.00   1.00    1.00    --  108.00 -61.00  30.00   43
 15  \w     44.00  75.00   1.00    1.00    --  108.00 -94.00 -60.00   31
 16  \w     96.00 162.00   1.00    1.00    --  108.00  45.00 120.00   66
 17  \w     42.00 109.00   1.00    1.00    --  108.00 -94.00   0.00   67
 18  \w     81.00 175.00   1.00    1.00    --  108.00  77.00   0.00   94
 19  \w     44.00  91.00   1.00    1.00    --  108.00 -30.00   0.00   47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0777691000
_diffrn_orient_matrix_UB_12      0.0269450000
_diffrn_orient_matrix_UB_13      0.1049174000
_diffrn_orient_matrix_UB_21      -0.0614262000
_diffrn_orient_matrix_UB_22      0.1789759000
_diffrn_orient_matrix_UB_23      0.0127365000
_diffrn_orient_matrix_UB_31      -0.0885447000
_diffrn_orient_matrix_UB_32      -0.1002670000
_diffrn_orient_matrix_UB_33      0.0510120000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3727
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         67.240
_diffrn_reflns_theta_min         4.608
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.121
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.35c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.139
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0062(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2054
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0387
_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^)+(0.0468P)^2^+0.1198P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0966
_refine_ls_wR_factor_ref         0.1066
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1609
_reflns_number_total             2054
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b02326_si_003.cif
_cod_data_source_block           exp_10434
_cod_database_code               4036060
_shelxl_version_number           2013-2
_shelx_estimated_absorpt_t_max   0.887
_shelx_estimated_absorpt_t_min   0.877
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C10(H10), C11(H11)
2.c Idealised tetrahedral OH refined as rotating group:
 O0AA(H0AA)
;
_shelx_res_checksum              40027
_shelx_hkl_checksum              39479
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.219
_oxdiff_exptl_absorpt_empirical_full_min 0.854