A Facile Access to Primary Alkylamines and Anilines via Ir(III)-Catalyzed C–H Amidation Using Azidoformates
Kim, Hyunwoo; Park, Gyeongtae; Park, Juhyeon; Chang, Sukbok; ACS Catalysis  (2016) 5922–; doi:10.1021/acscatal.6b01869

data_4513931
_publ_section_title
;
 A Facile Access to Primary Alkylamines and Anilines via Ir(III)-Catalyzed
 C--H Amidation Using Azidoformates
;
_journal_name_full               'ACS Catalysis'
_journal_page_first              5922
_journal_paper_doi               10.1021/acscatal.6b01869
_journal_year                    2016
_chemical_formula_sum            'C13 H24 N2 O3'
_chemical_formula_weight         256.34
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90.010(1)
_cell_angle_gamma                90
_cell_formula_units_Z            12
_cell_length_a                   17.0431(6)
_cell_length_b                   25.6881(9)
_cell_length_c                   10.2924(3)
_cell_measurement_reflns_used    9098
_cell_measurement_temperature    128(2)
_cell_measurement_theta_max      24.795
_cell_measurement_theta_min      2.662
_cell_volume                     4506.1(3)
_computing_cell_refinement       'Bruker SMART APEXll'
_computing_data_collection       'Bruker SMART APEXll'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXL-2013 (Sheldrick, 2013)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    SHELXTL
_diffrn_ambient_temperature      128(2)
_diffrn_measured_fraction_theta_full 0.936
_diffrn_measured_fraction_theta_max 0.947
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega phi scan'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1778
_diffrn_reflns_av_unetI/netI     0.1000
_diffrn_reflns_Laue_measured_fraction_full 0.936
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            93017
_diffrn_reflns_point_group_measured_fraction_full 0.928
_diffrn_reflns_point_group_measured_fraction_max 0.939
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.566
_diffrn_reflns_theta_min         2.390
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.8247
_exptl_absorpt_correction_T_min  0.2806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.134
_exptl_crystal_description       Block
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.110
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.086
_refine_ls_abs_structure_details
;
 Flack x determined using 2534 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.2(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     508
_refine_ls_number_reflns         9762
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.013
_refine_ls_R_factor_all          0.1088
_refine_ls_R_factor_gt           0.0673
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0871P)^2^+0.2367P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1430
_refine_ls_wR_factor_ref         0.1630
_reflns_Friedel_coverage         0.979
_reflns_Friedel_fraction_full    0.919
_reflns_Friedel_fraction_max     0.930
_reflns_number_gt                6807
_reflns_number_total             9762
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            cs6b01869_si_002.cif
_cod_data_source_block           othcc
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'MULTI-SCAN' changed to
'multi-scan' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/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_database_code               4513931
_shelx_estimated_absorpt_t_min   0.981
_shelx_estimated_absorpt_t_max   0.991
_shelxl_version_number           2013-4
_shelx_res_checksum              29874
_shelx_hkl_checksum              25831