Transition-Metal-Free Synthesis of β-Trifluoromethylated Enamines with Trifluoromethanesulfinate
Jiang, Huanfeng; Huang, Wei; Yu, Yue; Yi, Songjian; Li, Jiawei; Wu, Wanqing; Chem. Commun.  (2017) –; doi:10.1039/C7CC03125D

data_7120263
_publ_section_title
;
 Transition-Metal-Free Synthesis of \b-Trifluoromethylated Enamines with
 Trifluoromethanesulfinate
;
_journal_name_full               'Chem. Commun.'
_journal_paper_doi               10.1039/C7CC03125D
_journal_year                    2017
_chemical_formula_moiety         'C11 H9 F4 N O2'
_chemical_formula_sum            'C11 H9 F4 N O2'
_chemical_formula_weight         263.19
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-12-09
_audit_creation_method
;
Olex2 1.2
(compiled 2014.09.19 svn.r3010 for OlexSys, GUI svn.r4874)
;
_audit_update_record
;
2017-04-06 deposited with the CCDC.
2017-06-12 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 98.8820(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.57475(17)
_cell_length_b                   13.6182(2)
_cell_length_c                   8.60542(16)
_cell_measurement_reflns_used    2631
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      74.1590
_cell_measurement_theta_min      4.6550
_cell_volume                     1108.61(3)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 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    'olex2.solve (Bourhis et al., 2013)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2913
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.966
_diffrn_measured_fraction_theta_max 0.966
_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    -42.00  -3.00   1.00    1.00    --  -41.89 125.00-180.00   39
  2  \w   -110.00 -18.00   1.00    1.00    --  -41.89 -37.00 -60.00   92
  3  \w     95.00 151.00   1.00    1.01    --  108.44 125.00  30.00   56
  4  \w     82.00 172.00   1.00    1.01    --  108.44  61.00 150.00   90
  5  \w     80.00 138.00   1.00    1.01    --  108.44  30.00 120.00   58
  6  \w     89.00 131.00   1.00    1.01    --  108.44 -45.00 -60.00   42
  7  \w     48.00  74.00   1.00    1.01    --  108.44 -45.00 -60.00   26
  8  \w     48.00 140.00   1.00    1.01    --  108.44 -77.00   0.00   92
  9  \w     35.00  70.00   1.00    1.00    --   41.89-125.00   0.00   35
 10  \w     37.00  72.00   1.00    1.01    --  108.44-125.00 -30.00   35
 11  \w     24.00  98.00   1.00    1.00    --   41.89-125.00-150.00   74
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1491133000
_diffrn_orient_matrix_UB_12      -0.0455049000
_diffrn_orient_matrix_UB_13      0.0277780000
_diffrn_orient_matrix_UB_21      -0.0598975000
_diffrn_orient_matrix_UB_22      -0.0960862000
_diffrn_orient_matrix_UB_23      -0.0779317000
_diffrn_orient_matrix_UB_31      0.0263700000
_diffrn_orient_matrix_UB_32      0.0386411000
_diffrn_orient_matrix_UB_33      -0.1612247000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_av_unetI/netI     0.0287
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4161
_diffrn_reflns_theta_full        74.38
_diffrn_reflns_theta_max         74.38
_diffrn_reflns_theta_min         4.67
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.359
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.577
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.264
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2186
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.061
_refine_ls_R_factor_all          0.0404
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0592P)^2^+0.2326P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1036
_refine_ls_wR_factor_ref         0.1065
_reflns_number_gt                2026
_reflns_number_total             2186
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c7cc03125d2.cif
_cod_data_source_block           16112908
_cod_database_code               7120263
_chemical_oxdiff_formula         'C H O N F'
_chemical_oxdiff_usercomment     HW0823-1
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     67.29
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N7(H7), C8(H8), C14(H14), C15(H15), C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_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 2.165
_oxdiff_exptl_absorpt_empirical_full_min 0.587