Palladium-Catalyzed Sequential Acylation/Cyanation of Aryl Iodides: A Regiospecific Synthesis of 2-Cyanoaryl Ketones.
Pan, Shanfei; Wu, Feifei; Yu, Ruicheng; Chen, Wanzhi; The Journal of organic chemistry 81 (2016) 1558–1564; doi:10.1021/acs.joc.5b02710

data_4031869
_publ_section_title
;
 Palladium-Catalyzed Sequential Acylation/Cyanation of Aryl Iodides: A
 Regiospecific Synthesis of 2-Cyanoaryl Ketones.
;
_journal_issue                   4
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              1558
_journal_page_last               1564
_journal_paper_doi               10.1021/acs.joc.5b02710
_journal_volume                  81
_journal_year                    2016
_chemical_formula_sum            'C16 H13 N O2'
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_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                76.314(6)
_cell_angle_beta                 85.795(6)
_cell_angle_gamma                62.838(6)
_cell_formula_units_Z            2
_cell_length_a                   7.9139(5)
_cell_length_b                   8.2369(5)
_cell_length_c                   11.5044(8)
_cell_measurement_temperature    293(2)
_cell_volume                     647.76(8)
_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      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
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_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
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_diffrn_reflns_theta_full        25.01
_diffrn_reflns_theta_max         25.01
_diffrn_reflns_theta_min         2.90
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9806
_exptl_absorpt_correction_T_min  0.9699
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             264
_exptl_crystal_size_max          0.36
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_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.146
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_refine_ls_extinction_method     none
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_refine_ls_number_parameters     174
_refine_ls_number_reflns         2275
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0648
_refine_ls_R_factor_gt           0.0448
_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^)+(0.0509P)^2^+0.1627P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1239
_reflns_number_gt                1699
_reflns_number_total             2275
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo5b02710_si_001.cif
_cod_data_source_block           151022_50928_1_2
_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 
;
_cod_original_cell_volume        647.76(7)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4031869