Transition metal catalysed C7 and ortho-selective halogenation of 2-arylbenzo[d]oxazoles
Hong, Xi; Zhou, Quan; Huang, Shuang; Cui, He-Zhen; Li, Zhi-Ming; Hou, Xiu-Feng; Organic Chemistry Frontiers 6 (2019) 2226–; doi:10.1039/C9QO00429G

data_1554911
_publ_section_title
;
 Transition metal catalysed C7 and ortho-selective halogenation of
 2-arylbenzo[d]oxazoles
;
_journal_issue                   13
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2226
_journal_paper_doi               10.1039/C9QO00429G
_journal_volume                  6
_journal_year                    2019
_chemical_formula_sum            'C27 H29 F6 N2 O P Ru'
_chemical_formula_weight         643.56
_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-2014/7
_audit_update_record
;
2019-03-19 deposited with the CCDC.	2019-04-30 downloaded from the CCDC.
;
_cell_angle_alpha                92.7480(10)
_cell_angle_beta                 96.7020(10)
_cell_angle_gamma                90.4760(10)
_cell_formula_units_Z            2
_cell_length_a                   10.7138(3)
_cell_length_b                   10.8978(3)
_cell_length_c                   12.0990(3)
_cell_measurement_reflns_used    9990
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      58.14
_cell_measurement_theta_min      3.53
_cell_volume                     1401.24(7)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34138
_diffrn_reflns_av_R_equivalents  0.0368
_diffrn_reflns_av_unetI/netI     0.0234
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            40468
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         58.144
_diffrn_reflns_theta_min         3.204
_exptl_absorpt_coefficient_mu    3.783
_exptl_absorpt_correction_T_max  0.772
_exptl_absorpt_correction_T_min  0.634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_description       rod
_exptl_crystal_F_000             652
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     404
_refine_ls_number_reflns         5953
_refine_ls_number_restraints     72
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0258
_refine_ls_R_factor_gt           0.0242
_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^)+(0.0382P)^2^+0.3742P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0648
_refine_ls_wR_factor_ref         0.0659
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5638
_reflns_number_total             5953
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9qo00429g2.cif
_cod_data_source_block           ga_81008a_a
_cod_database_code               1554911
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.253
_shelx_estimated_absorpt_t_max   0.863
_shelx_res_checksum              78100
_shelx_hkl_checksum              36018