A new approach to access difluoroalkylated diarylmethanes via visible-light photocatalytic cross-coupling reactions.
Zhao, Yin-Na; Luo, Yong-Chun; Wang, Zhu-Yin; Xu, Peng-Fei; Chemical communications (Cambridge, England) 54 (2018) 3993–3996; doi:10.1039/c8cc01486h

data_7121437
_publ_section_title
;
 A new approach to access difluoroalkylated diarylmethanes via
 visible-light photocatalytic cross-coupling reactions.
;
_journal_issue                   32
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              3993
_journal_page_last               3996
_journal_paper_doi               10.1039/c8cc01486h
_journal_volume                  54
_journal_year                    2018
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C28 H37 F2 N O2'
_chemical_formula_sum            'C28 H37 F2 N O2'
_chemical_formula_weight         457.59
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_Hall           'P -2yac'
_space_group_name_H-M_alt        'P 1 n 1'
_symmetry_space_group_name_Hall  'P -2yac'
_symmetry_space_group_name_H-M   'P 1 n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-10-13
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-10-17 deposited with the CCDC.
2018-03-22 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 91.516(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.6409(9)
_cell_length_b                   9.1391(7)
_cell_length_c                   12.7748(10)
_cell_measurement_reflns_used    1632
_cell_measurement_temperature    294.47(10)
_cell_measurement_theta_max      26.5150
_cell_measurement_theta_min      3.9050
_cell_volume                     1241.89(17)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.47(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
  1 omega  -17.00   17.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055   57.0000 -120.0000 17

  2 omega    4.00   92.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000   90.0000 44

  3 omega  -47.00   47.00   2.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000  -60.0000 47
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0194929000
_diffrn_orient_matrix_UB_12      -0.0401340000
_diffrn_orient_matrix_UB_13      0.0450542000
_diffrn_orient_matrix_UB_21      0.0238561000
_diffrn_orient_matrix_UB_22      -0.0559536000
_diffrn_orient_matrix_UB_23      -0.0323995000
_diffrn_orient_matrix_UB_31      0.0592193000
_diffrn_orient_matrix_UB_32      0.0357704000
_diffrn_orient_matrix_UB_33      -0.0001284000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0641
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            4327
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.37
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81137
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.5(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.969
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         3189
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      0.968
_refine_ls_R_factor_all          0.0625
_refine_ls_R_factor_gt           0.0494
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1330
_refine_ls_wR_factor_ref         0.1499
_reflns_number_gt                2694
_reflns_number_total             3189
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c8cc01486h2.cif
_cod_data_source_block           zhaoyn_0919
_cod_depositor_comments          'Adding full bibliography for 7121437.cif.'
_cod_database_code               7121437
_reflns_odcompleteness_completeness 99.37
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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
2. Restrained distances
 H1-H9B
 2 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C21(H21)
3.b Secondary CH2 refined with riding coordinates:
 C25(H25A,H25B), C28(H28A,H28B), C24(H24A,H24B), C26(H26A,H26B), C27(H27A,H27B)
3.c Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C15(H15), C19(H19), C17(H17), C18(H18), C16(H16)
3.d Idealised Me refined as rotating group:
 C8(H8A,H8B,H8C), C10(H10A,H10B,H10C), C9(H9A,H9B,H9C), C13(H13A,H13B,H13C),
 C14(H14A,H14B,H14C), C12(H12A,H12B,H12C)
;
_olex2_date_sample_data_collection 2017-09-19
_olex2_submission_special_instructions 'No special instructions were received'