Synthesis of o-Alkenylated 2-Arylbenzoxazoles via Rh-Catalyzed Oxidative Olefination of 2-Arylbenzoxazoles: Scope Investigation, Structural Features, and Mechanism Studies.
Zhou, Quan; Zhang, Jing-Fan; Cao, Hui; Zhong, Rui; Hou, Xiu-Feng; The Journal of organic chemistry 81 (2016) 12169–12180; doi:10.1021/acs.joc.6b01836

data_4037242
_publ_section_title
;
 Synthesis of o-Alkenylated 2-Arylbenzoxazoles via Rh-Catalyzed Oxidative
 Olefination of 2-Arylbenzoxazoles: Scope Investigation, Structural
 Features, and Mechanism Studies.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              12169
_journal_page_last               12180
_journal_paper_doi               10.1021/acs.joc.6b01836
_journal_volume                  81
_journal_year                    2016
_chemical_formula_sum            'C21 H20 F N O3'
_chemical_formula_weight         353.38
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                112.171(6)
_cell_angle_beta                 97.626(7)
_cell_angle_gamma                105.108(6)
_cell_formula_units_Z            2
_cell_length_a                   7.832(4)
_cell_length_b                   10.744(5)
_cell_length_c                   12.557(6)
_cell_measurement_reflns_used    590
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.502
_cell_measurement_theta_min      2.898
_cell_volume                     912.6(8)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0645
_diffrn_reflns_av_unetI/netI     0.0786
_diffrn_reflns_Laue_measured_fraction_full 0.957
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3817
_diffrn_reflns_point_group_measured_fraction_full 0.957
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.008
_diffrn_reflns_theta_min         1.813
_exptl_absorpt_coefficient_mu    0.093
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       0.018(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.902
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3160
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.902
_refine_ls_R_factor_all          0.1064
_refine_ls_R_factor_gt           0.0601
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; 

 w=1/[\s^2^(Fo^2^)+(0.0892P)^2^] 

 where P=(Fo^2^+2Fc^2^)/3 

;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1430
_refine_ls_wR_factor_ref         0.1586
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1615
_reflns_number_total             3160
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo6b01836_si_002.cif
_cod_data_source_block           a60226a
_cod_original_cell_volume        912.7(8)
_cod_database_code               4037242
_shelx_estimated_absorpt_t_min   0.964
_shelx_estimated_absorpt_t_max   0.995
_shelxl_version_number           2013-2
_shelx_res_checksum              64580
_shelx_hkl_checksum              13056