Unified Synthesis of Multiply Arylated Alkanes by Catalytic Deoxygenative Transformation of Diarylketones
Kurosawa, Miki B.; Kato, Kenta; Muto, Kei; Yamaguchi, Junichiro; Chemical Science  (2022) –; doi:10.1039/D2SC03720C

data_1567513
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.

Sheldrick, G.M. (2015). Acta Cryst. C71, 3-8.
;
_publ_section_title
;
 Unified Synthesis of Multiply Arylated Alkanes by Catalytic Deoxygenative
 Transformation of Diarylketones
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC03720C
_journal_year                    2022
_chemical_formula_moiety         'C13 H11'
_chemical_formula_sum            'C13 H11'
_chemical_formula_weight         167.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-09
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-03-16 deposited with the CCDC.	2022-08-22 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.211(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.661(3)
_cell_length_b                   5.8999(12)
_cell_length_c                   17.598(3)
_cell_measurement_reflns_used    4763
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      136.38
_cell_measurement_theta_min      10.02
_cell_volume                     1833.3(6)
_computing_cell_refinement       'Rigaku RAPID-AUTO'
_computing_data_collection       'Rigaku RAPID-AUTO'
_computing_data_reduction        'Rigaku RAPID-AUTO'
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      173.15
_diffrn_detector_area_resol_mean 10
_diffrn_detector_type            'Rigaku IP'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku R-AXIS SPIDER IP'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            9136
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.680
_diffrn_reflns_theta_max         68.184
_diffrn_reflns_theta_min         5.009
_exptl_absorpt_coefficient_mu    0.513
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8221
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'JABSCOR (Rigaku, 1995)'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.166
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         1672
_refine_ls_number_restraints     31
_refine_ls_restrained_S_all      1.163
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0486
_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^)+(0.0522P)^2^+0.5525P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1138
_refine_ls_wR_factor_ref         0.1283
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1252
_reflns_number_total             1672
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc03720c2.cif
_cod_data_source_block           3A
_cod_original_cell_volume        1833.4(6)
_cod_database_code               1567513
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2. Restrained distances
 C4-C5 \\sim C26-C25
 with sigma of 0.02
 C4-C3 \\sim C26-C27
 with sigma of 0.02
 C8-C2 \\sim C16-C22
 with sigma of 0.04
 C5-C6 \\sim C25-C24
 with sigma of 0.02
 C3-C2 \\sim C27-C22
 with sigma of 0.02
 C14-C1 \\sim C17-C15
 with sigma of 0.04
 C13-C14 \\sim C18-C17
 with sigma of 0.02
 C13-C12 \\sim C18-C19
 with sigma of 0.02
 C14-C8 \\sim C17-C16
 with sigma of 0.02
 C8-C10 \\sim C16-C21
 with sigma of 0.02
 C8-C1 \\sim C16-C15
 with sigma of 0.02
 C14-C12 \\sim C17-C19
 with sigma of 0.04
 C12-C10 \\sim C19-C21
 with sigma of 0.04
 C12-C11 \\sim C19-C20
 with sigma of 0.02
 C2-C6 \\sim C22-C24
 with sigma of 0.04
 C2-C7 \\sim C22-C23
 with sigma of 0.02
 C2-C1 \\sim C22-C15
 with sigma of 0.02
 C6-C7 \\sim C24-C23
 with sigma of 0.02
 C11-C10 \\sim C20-C21
 with sigma of 0.02
 C14-C10 \\sim C17-C21
 with sigma of 0.04
 C8-C11 \\sim C16-C20
 with sigma of 0.04
 C4-C2 \\sim C26-C22
 with sigma of 0.04
 C4-C6 \\sim C26-C24
 with sigma of 0.04
 C5-C3 \\sim C25-C27
 with sigma of 0.04
 C7-C1 \\sim C23-C15
 with sigma of 0.04
 C5-C7 \\sim C25-C23
 with sigma of 0.04
 C10-C1 \\sim C21-C15
 with sigma of 0.04
 C3-C7 \\sim C27-C23
 with sigma of 0.04
 C3-C1 \\sim C27-C15
 with sigma of 0.04
 C13-C8 \\sim C18-C16
 with sigma of 0.04
 C13-C11 \\sim C18-C20
 with sigma of 0.04
3. Others
 Sof(C15)=Sof(H15)=Sof(C26)=Sof(H26)=Sof(C25)=Sof(H25)=Sof(C27)=Sof(H27)=
 Sof(C24)=Sof(H24)=Sof(C22)=Sof(C23)=Sof(H23)=Sof(C16)=Sof(C17)=Sof(H17)=
 Sof(C21)=Sof(H21)=Sof(C18)=Sof(H18)=Sof(C20)=Sof(H20)=Sof(C19)=Sof(H19)=1-
 FVAR(1)
 Sof(C4)=Sof(H4)=Sof(C5)=Sof(H5)=Sof(C3)=Sof(H3)=Sof(C13)=Sof(H13)=Sof(C14)=
 Sof(H14)=Sof(C8)=Sof(C12)=Sof(H12)=Sof(C2)=Sof(C6)=Sof(H6)=Sof(C11)=Sof(H11)=
 Sof(C7)=Sof(H7)=Sof(C10)=Sof(H10)=Sof(C1)=Sof(H1)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C1(H1), C15(H15)
4.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C3(H3), C13(H13), C14(H14), C12(H12), C6(H6), C11(H11),
 C7(H7), C10(H10), C26(H26), C25(H25), C27(H27), C24(H24), C23(H23), C17(H17),
 C21(H21), C18(H18), C20(H20), C19(H19)
;
_shelx_res_checksum              29650
_olex2_submission_special_instructions 'No special instructions were received'