RhI/RhIIIcatalyst-controlled divergent aryl/heteroaryl C–H bond functionalization of picolinamides with alkynes
Martínez, Ángel Manu; Echavarren, Javier; Alonso, Inés; Rodríguez, Nuria; Gómez Arrayás, Ramón; Carretero, Juan C.; Chem. Sci. 6 (2015) 5802–; doi:10.1039/C5SC01885D

data_1520697
_publ_section_title
;
 RhI/RhIIIcatalyst-controlled divergent aryl/heteroaryl C--H bond
 functionalization of picolinamides with alkynes
;
_journal_issue                   10
_journal_name_full               'Chem. Sci.'
_journal_page_first              5802
_journal_paper_doi               10.1039/C5SC01885D
_journal_volume                  6
_journal_year                    2015
_chemical_formula_moiety         'C28 H19 F3 N2 O'
_chemical_formula_sum            'C28 H19 F3 N2 O'
_chemical_formula_weight         456.45
_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
_audit_update_record
;
2014-10-02 deposited with the CCDC.
2015-06-29 downloaded from the CCDC.
;
_cell_angle_alpha                103.037(2)
_cell_angle_beta                 100.267(2)
_cell_angle_gamma                97.7300(10)
_cell_formula_units_Z            2
_cell_length_a                   9.7447(3)
_cell_length_b                   10.0599(3)
_cell_length_c                   12.2374(4)
_cell_measurement_reflns_used    3225
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      65.38
_cell_measurement_theta_min      3.80
_cell_volume                     1130.75(6)
_computing_cell_refinement       'SAINT (Bruker 2006)'
_computing_data_collection       'APEX 2 (Bruker 2006)'
_computing_data_reduction        'SAINT (Bruker 2006)'
_computing_molecular_graphics    'Mercury 2.3 (Macrae et al, 2008)'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.856
_diffrn_measured_fraction_theta_max 0.856
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0194
_diffrn_reflns_av_sigmaI/netI    0.0271
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6730
_diffrn_reflns_theta_full        66.68
_diffrn_reflns_theta_max         66.68
_diffrn_reflns_theta_min         3.80
_exptl_absorpt_coefficient_mu    0.827
_exptl_absorpt_correction_T_max  0.883
_exptl_absorpt_correction_T_min  0.848
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2006)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.321
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0222(13)
_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   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         3427
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0549
_refine_ls_R_factor_gt           0.0489
_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^)+(0.0692P)^2^+0.4507P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1334
_refine_ls_wR_factor_ref         0.1394
_reflns_number_gt                2982
_reflns_number_total             3427
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c5sc01885d2.cif
_cod_data_source_block           2fin
_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/rss-feeds/RSC/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 3271 2015-04-21 07:52:19Z andrius 

 Adding full bibliography for 1520695--1520700.cif.
;
_cod_original_cell_volume        1130.74(6)
_cod_original_sg_symbol_Hall     -P1
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1520697