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_4037221
_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         'C18 H18 N2 O3'
_chemical_formula_sum            'C18 H18 N2 O3'
_chemical_formula_weight         310.34
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_Int_Tables_number      2
_atom_sites_solution_primary     direct
_audit_creation_date             2016-04-02
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                115.006(4)
_cell_angle_beta                 90.240(4)
_cell_angle_gamma                100.357(4)
_cell_formula_units_Z            4
_cell_length_a                   7.2107(7)
_cell_length_b                   14.9108(14)
_cell_length_c                   16.2218(15)
_cell_measurement_reflns_used    9807
_cell_measurement_temperature    159(2)
_cell_measurement_theta_max      25.08
_cell_measurement_theta_min      2.88
_cell_volume                     1548.6(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_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)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      159.14
_diffrn_measured_fraction_theta_full 0.9837
_diffrn_measured_fraction_theta_max 0.9837
_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  0.0804
_diffrn_reflns_av_unetI/netI     0.0496
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            31519
_diffrn_reflns_theta_full        26.0000
_diffrn_reflns_theta_max         25.17
_diffrn_reflns_theta_min         2.48
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6468
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1589 before and 0.0728 after correction.
The Ratio of minimum to maximum transmission is 0.8680.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.3311
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             656.0
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.7646
_refine_diff_density_min         -0.4632
_refine_diff_density_rms         0.1095
_refine_ls_d_res_high            0.8355
_refine_ls_d_res_low             8.2168
_refine_ls_goodness_of_fit_ref   1.0717
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    60
_refine_ls_number_parameters     418
_refine_ls_number_reflns         5480
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0717
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0776
_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^)+(0.1277P)^2^+1.6890P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2056
_refine_ls_wR_factor_ref         0.2206
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              8
_reflns_limit_h_min              -8
_reflns_limit_k_max              15
_reflns_limit_k_min              -17
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                4254
_reflns_number_total             5468
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            jo6b01771_si_006.cif
_cod_data_source_block           VR_213_L
_cod_database_code               4037221
_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.a Secondary CH2 refined with riding coordinates:
 C00S(H00e,H00f), C00W(H00a,H00b), C00Z(H00c,H00d), C011(H01g,H01h)
2.b Aromatic/amide H refined with riding coordinates:
 C00I(H00I), C00L(H00L), C00M(H00M), C00P(H00P), C00Q(H00Q), C00R(H00R),
 C00T(H00T), C00V(H00V), C00X(H00X), C00Y(H00Y), C010(H010), C012(H012),
 C013(H013), C014(H014), C019(H019), C01A(H01o)
2.c Idealised Me refined as rotating group:
 C015(H01i,H01j,H01k), C016(H01a,H01b,H01c), C017(H01d,H01e,H01f), C018(H01l,
 H01m,H01n)
;
_olex2_submission_special_instructions 'No special instructions were received'