Photoredox-Catalyzed Cascade Radical Cyclization of Ester Arylpropiolates with CF<sub>3</sub>SO<sub>2</sub>Cl To Construct 3-Trifluoromethyl Coumarin Derivatives.
Chen, Long; Wu, Lianlian; Duan, Weijie; Wang, Tao; Li, Letian; Zhang, Keke; Zhu, Jingmei; Peng, Zhi; Xiong, Fei; The Journal of organic chemistry 83 (2018) 8607–8614; doi:10.1021/acs.joc.8b00581

data_4035549
_publ_section_title
;
 Photoredox-Catalyzed Cascade Radical Cyclization of Ester Arylpropiolates
 with CF<sub>3</sub>SO<sub>2</sub>Cl To Construct 3-Trifluoromethyl
 Coumarin Derivatives.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8607
_journal_page_last               8614
_journal_paper_doi               10.1021/acs.joc.8b00581
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C17 H11 F3 O2'
_chemical_formula_sum            'C17 H11 F3 O2'
_chemical_formula_weight         304.26
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2017-03-14
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.308(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.4148(5)
_cell_length_b                   7.9614(4)
_cell_length_c                   14.3307(6)
_cell_measurement_reflns_used    5482
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.3840
_cell_measurement_theta_min      4.1000
_cell_volume                     1414.07(11)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0353
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.898
_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    -35.00  53.00   1.00    3.95    --  -15.92  37.00 150.00   88
  2  \w    -88.00 -35.00   1.00    3.95    --  -15.92-178.00 120.00   53
  3  \w    -45.00  55.00   1.00    3.95    --  -15.92  19.00  90.00  100
  4  \w    -52.00  36.00   1.00    3.95    --   16.85 -37.00-120.00   88
  5  \w      0.00  84.00   1.00    3.95    --   16.85  57.00-180.00   84
  6  \w    -20.00   5.00   1.00    3.95    --   16.85 -99.00  30.00   25
  7  \w    -10.00  84.00   1.00    3.95    --   16.85  77.00  30.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0247802000
_diffrn_orient_matrix_UB_12      -0.0532202000
_diffrn_orient_matrix_UB_13      -0.0321656000
_diffrn_orient_matrix_UB_21      0.0373823000
_diffrn_orient_matrix_UB_22      -0.0274290000
_diffrn_orient_matrix_UB_23      0.0360919000
_diffrn_orient_matrix_UB_31      -0.0355541000
_diffrn_orient_matrix_UB_32      -0.0659918000
_diffrn_orient_matrix_UB_33      0.0109375000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.898
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            16163
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.898
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.397
_diffrn_reflns_theta_min         3.318
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70016
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (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    1.429
_exptl_crystal_description       needle
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         3502
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0522
_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^)+(0.0520P)^2^+0.4100P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1237
_refine_ls_wR_factor_ref         0.1353
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2541
_reflns_number_total             3502
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b00581_si_002.cif
_cod_data_source_block           cl20170310
_cod_original_cell_volume        1414.08(11)
_cod_database_code               4035549
_shelxl_version_number           2014-1
_reflns_odcompleteness_completeness 99.68
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C8(H8), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_shelx_res_checksum              61347
_shelx_hkl_checksum              35327
_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 1.535
_oxdiff_exptl_absorpt_empirical_full_min 0.542