RuHCl(CO)(PPh<sub>3</sub>)<sub>3</sub>-Catalyzed Direct Amidation of Arene C-H Bond with Azides.
Xiao, Xinsheng; Jia, Guokai; Liu, Fang; Ou, Guangchuan; Xie, Ying; The Journal of organic chemistry 83 (2018) 13811–13820; doi:10.1021/acs.joc.8b02123

data_4034850
_publ_section_title
;
 RuHCl(CO)(PPh<sub>3</sub>)<sub>3</sub>-Catalyzed Direct Amidation of
 Arene C-H Bond with Azides.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              13811
_journal_page_last               13820
_journal_paper_doi               10.1021/acs.joc.8b02123
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C20 H16 N2 O2 S'
_chemical_formula_sum            'C20 H16 N2 O2 S'
_chemical_formula_weight         348.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-10-14
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 91.360(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.312(3)
_cell_length_b                   8.177(3)
_cell_length_c                   27.472(11)
_cell_measurement_reflns_used    8030
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.30
_cell_measurement_theta_min      2.49
_cell_volume                     1642.1(11)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_unetI/netI     0.0140
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            16869
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.499
_diffrn_reflns_theta_min         1.483
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.213
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0712 before and 0.0305 after correction.
The Ratio of minimum to maximum transmission is 0.9183.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.23
_refine_diff_density_max         0.467
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3375
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0479
_refine_ls_R_factor_gt           0.0424
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0758P)^2^+0.3719P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1204
_refine_ls_wR_factor_ref         0.1255
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2940
_reflns_number_total             3375
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02123_si_002.cif
_cod_data_source_block           1
_cod_database_code               4034850
_shelx_shelxl_version_number     2016/6
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 N005(H005)
2.b Aromatic/amide H refined with riding coordinates:
 C00B(H00B), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H),
 C00I(H00I), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O)
2.c Idealised Me refined as rotating group:
 C00P(H00A,H00C,H00J)
;
_shelx_res_checksum              124
_shelx_hkl_checksum              29919
_olex2_submission_special_instructions 'No special instructions were received'