Palladium-Catalyzed Sequential Heteroarylation/Acylation Reactions of Iodobenzenes: Synthesis of Functionalized Benzo[ d]oxazoles.
Zhang, Pingshun; Pan, Shanfei; Chen, Wanzhi; Liu, Miaochang; Wu, Huayue; The Journal of organic chemistry 83 (2018) 3354–3360; doi:10.1021/acs.joc.7b03055

data_4033519
_publ_section_title
;
 Palladium-Catalyzed Sequential Heteroarylation/Acylation Reactions of
 Iodobenzenes: Synthesis of Functionalized Benzo[ d]oxazoles.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3354
_journal_page_last               3360
_journal_paper_doi               10.1021/acs.joc.7b03055
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C20 H16 F2 N2 O3'
_chemical_formula_weight         370.35
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 96.896(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.3289(5)
_cell_length_b                   14.3422(11)
_cell_length_c                   18.7478(15)
_cell_measurement_reflns_used    1910
_cell_measurement_temperature    169.9
_cell_measurement_theta_max      29.3696
_cell_measurement_theta_min      2.8347
_cell_volume                     1689.4(2)
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_collection       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_sigmaI/netI    0.0466
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            6531
_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.84
_exptl_absorpt_coefficient_mu    0.114
_exptl_absorpt_correction_T_max  0.9821
_exptl_absorpt_correction_T_min  0.9743
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             768
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.201
_refine_diff_density_min         -0.201
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2979
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0477
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0542P)^2^+0.2872P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1110
_refine_ls_wR_factor_ref         0.1283
_reflns_number_gt                2157
_reflns_number_total             2979
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b03055_si_002.cif
_cod_data_source_block           161228_zps_61227
_cod_depositor_comments          'Adding full bibliography for 4033519.cif.'
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4033519