Para-Selective Cu-Catalyzed C-H Aryloxylation of Electron-Rich Arenes and Heteroarenes.
Sokolovs, Igors; Suna, Edgars; The Journal of organic chemistry 81 (2016) 371–379; doi:10.1021/acs.joc.5b02728

data_4031847
_publ_section_title
;
 Para-Selective Cu-Catalyzed C-H Aryloxylation of Electron-Rich Arenes and
 Heteroarenes.
;
_journal_issue                   2
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              371
_journal_page_last               379
_journal_paper_doi               10.1021/acs.joc.5b02728
_journal_volume                  81
_journal_year                    2016
_chemical_compound_source        'Local laboratory'
_chemical_formula_moiety         'C21 H22 Br I N O2, C6 H4 N O3, C6 H5 N O3'
_chemical_formula_sum            'C33 H31 Br I N3 O8'
_chemical_formula_weight         804.428
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           maXus
_cell_angle_alpha                75.2788(7)
_cell_angle_beta                 88.3395(7)
_cell_angle_gamma                83.2541(12)
_cell_formula_units_Z            2
_cell_length_a                   8.70520(10)
_cell_length_b                   12.2035(2)
_cell_length_c                   16.0777(4)
_cell_measurement_reflns_used    14338
_cell_measurement_temperature    183
_cell_measurement_theta_max      28.5
_cell_measurement_theta_min      0.9
_cell_volume                     1640.49(5)
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_collection       KappaCCD
_computing_data_reduction        'Denzo and Scalepak (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'Ortep (Johnson, 1976)'
_computing_publication_material  'maXus(Mackay et al., 1999)'
_computing_structure_refinement  'maXus(Mackay et al., 1999)'
_computing_structure_solution
'SIR97(Cascarano al.,Acta Cryst.,1996,A52,C-79)'
_diffrn_ambient_temperature      183(2)
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.98
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       '\f and \w scan'
_diffrn_orient_matrix_type       X=UH
_diffrn_orient_matrix_UB_11      0.00279
_diffrn_orient_matrix_UB_12      0.09043
_diffrn_orient_matrix_UB_13      -0.07207
_diffrn_orient_matrix_UB_21      0.06841
_diffrn_orient_matrix_UB_22      0.02204
_diffrn_orient_matrix_UB_23      0.04589
_diffrn_orient_matrix_UB_31      0.02318
_diffrn_orient_matrix_UB_32      -0.03778
_diffrn_orient_matrix_UB_33      -0.04660
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           ' MoK\a'
_diffrn_radiation_wavelength_id  all
_diffrn_reflns_av_R_equivalents  0.025
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11515
_diffrn_reflns_theta_full        29.0
_diffrn_reflns_theta_max         29.0
_diffrn_reflns_theta_min         3.3
_exptl_absorpt_coefficient_mu    2.25
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Prism
_exptl_crystal_F_000             804
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.85
_refine_diff_density_min         -1.35
_refine_diff_density_rms         0.10
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_all   1.037
_refine_ls_goodness_of_fit_gt    1.009
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    31
_refine_ls_number_parameters     415
_refine_ls_number_reflns         7257
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.043
_refine_ls_R_factor_gt           0.034
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef F^2^
_refine_ls_weighting_details     ' w = 1 / ( s^2^(Fo^2^) + 0.10000 * Fo^2^)'
_refine_ls_weighting_scheme      sigma
_refine_ls_wR_factor_all         0.068
_refine_ls_wR_factor_gt          0.066
_refine_ls_wR_factor_ref         0.066
_reflns_d_resolution_high        0.61
_reflns_d_resolution_low         1.73
_reflns_limit_h_max              11
_reflns_limit_h_min              0
_reflns_limit_k_max              16
_reflns_limit_k_min              -16
_reflns_limit_l_max              21
_reflns_limit_l_min              -21
_reflns_number_gt                7266
_reflns_number_total             8629
_reflns_threshold_expression     'I> 3.00 sigma(I)'
_cod_data_source_file            jo5b02728_si_002.cif
_cod_data_source_block           Dmitry
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas 

The following automatic conversions were performed:

'_atom_sites_solution_hydrogens' value 'geom, diff' was changed to
'mixed'.

Automatic conversion script
Id: cif_fix_values 6452 2018-10-05 10:23:21Z andrius 
;
_cod_original_sg_symbol_H-M      'P -1          '
_cod_original_formula_sum        'C33 H31 Br I N3 O8 '
_cod_database_code               4031847