Synthesis of Unsymmetrical Diaryl Acetamides, Benzofurans, Benzophenones, and Xanthenes by Transition-Metal-Free Oxidative Cross-Coupling of sp<sup>3</sup> and sp<sup>2</sup> C-H Bonds.
Rathore, Vandana; Sattar, Moh; Kumar, Raushan; Kumar, Sangit; The Journal of organic chemistry 81 (2016) 9206–9218; doi:10.1021/acs.joc.6b01771

data_4037224
_publ_section_title
;
 Synthesis of Unsymmetrical Diaryl Acetamides, Benzofurans, Benzophenones,
 and Xanthenes by Transition-Metal-Free Oxidative Cross-Coupling of
 sp<sup>3</sup> and sp<sup>2</sup> C-H Bonds.
;
_journal_issue                   19
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9206
_journal_page_last               9218
_journal_paper_doi               10.1021/acs.joc.6b01771
_journal_volume                  81
_journal_year                    2016
_chemical_formula_moiety         'C20 H22 Cl N2 O2'
_chemical_formula_sum            'C20 H22 Cl N2 O2'
_chemical_formula_weight         357.85
_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_Int_Tables_number      14
_audit_creation_date             2016-02-02
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.684(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.5362(7)
_cell_length_b                   16.2261(12)
_cell_length_c                   14.2507(12)
_cell_measurement_reflns_used    3431
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      20.30
_cell_measurement_theta_min      2.51
_cell_volume                     1973.7(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.9976
_diffrn_measured_fraction_theta_max 0.9976
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0756
_diffrn_reflns_av_unetI/netI     0.0951
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            22894
_diffrn_reflns_theta_full        30.0899
_diffrn_reflns_theta_max         30.09
_diffrn_reflns_theta_min         2.51
_exptl_absorpt_coefficient_mu    0.208
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             756.0
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.5446
_refine_diff_density_min         -0.5811
_refine_diff_density_rms         0.1244
_refine_ls_d_res_high            0.7088
_refine_ls_d_res_low             8.1130
_refine_ls_goodness_of_fit_ref   1.0964
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    38
_refine_ls_number_parameters     256
_refine_ls_number_reflns         5790
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0964
_refine_ls_R_factor_all          0.1895
_refine_ls_R_factor_gt           0.0767
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0435P)^2^+1.3487P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1595
_refine_ls_wR_factor_ref         0.1948
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -11
_reflns_limit_k_max              22
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                2637
_reflns_number_total             5804
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo6b01771_si_002.cif
_cod_data_source_block           VR142_c
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4037224
_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. Others
 Fixed Sof: O2(0.5) O3(0.5) Cl2(0.5) Cl1(0.5) N2b(0.5) N2a(0.5) H6(0.5)
 H2(0.5) H3a(0.5) H2a(0.5)
3.a Ternary CH refined with riding coordinates:
 C10(H10), C12(H12)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C20(H20), C19(H19), C18(H18), C17(H17), C16(H16), C6(H6),
 C2(H2)
3.c Idealised Me refined as rotating group:
 C13(H13a,H13b,H13c), C11(H11a,H11b,H11c), C9(H9a,H9b,H9c), C14(H14a,H14b,H14c)
;
_olex2_submission_special_instructions 'No special instructions were received'