Iridium-Catalyzed ortho-C(sp<sup>2</sup>)-H Amidation of Benzaldehydes with Organic Azides.
Mu, Delong; Wang, Xinmou; Chen, Gong; He, Gang; The Journal of organic chemistry 82 (2017) 4497–4503; doi:10.1021/acs.joc.7b00531

data_4037487
_publ_section_title
;
 Iridium-Catalyzed ortho-C(sp<sup>2</sup>)-H Amidation of Benzaldehydes
 with Organic Azides.
;
_journal_issue                   8
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              4497
_journal_page_last               4503
_journal_paper_doi               10.1021/acs.joc.7b00531
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C16 H15 N O5 S'
_chemical_formula_sum            'C16 H15 N O5 S'
_chemical_formula_weight         333.35
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-01-16
_audit_creation_method
;
Olex2 1.2
(compiled 2017.01.04 svn.r3372 for OlexSys, GUI svn.r5292)
;
_cell_angle_alpha                77.869(6)
_cell_angle_beta                 87.177(7)
_cell_angle_gamma                64.169(9)
_cell_formula_units_Z            2
_cell_length_a                   8.7800(9)
_cell_length_b                   8.8815(7)
_cell_length_c                   11.5174(8)
_cell_measurement_reflns_used    2041
_cell_measurement_temperature    297.4(3)
_cell_measurement_theta_max      27.8970
_cell_measurement_theta_min      3.6150
_cell_volume                     789.42(13)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.4(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2116
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -43.00  53.00   1.00    3.00    --  -19.25  37.00  30.00   96
  2  \w     -8.00  18.00   1.00    3.00    --   18.94  77.00   0.00   26
  3  \w    -39.00   4.00   1.00    3.00    --  -19.25 -77.00  30.00   43
  4  \w    -83.00   2.00   1.00    3.00    --  -19.25 -64.00 114.00   85
  5  \w    -46.00  51.00   1.00    3.00    --  -19.25  77.00-120.00   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0224858000
_diffrn_orient_matrix_UB_12      0.0449931000
_diffrn_orient_matrix_UB_13      0.0469846000
_diffrn_orient_matrix_UB_21      -0.0797574000
_diffrn_orient_matrix_UB_22      -0.0024669000
_diffrn_orient_matrix_UB_23      0.0016513000
_diffrn_orient_matrix_UB_31      0.0347490000
_diffrn_orient_matrix_UB_32      -0.0787714000
_diffrn_orient_matrix_UB_33      0.0420343000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0177
_diffrn_reflns_av_unetI/netI     0.0355
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4699
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.007
_diffrn_reflns_theta_max         25.007
_diffrn_reflns_theta_min         3.056
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.230
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59071
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.329
_refine_diff_density_min         -0.334
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         2776
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0432
_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^)+(0.0561P)^2^+0.1597P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1067
_refine_ls_wR_factor_ref         0.1169
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2229
_reflns_number_total             2776
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b00531_si_002.cif
_cod_data_source_block           65A
_cod_database_code               4037487
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C N O S H'
_chemical_oxdiff_usercomment     MDL-06-65A3
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 Aromatic/amide H refined with riding coordinates:
 C3(H3), C14(H14), C6(H6), C11(H11), C4(H4), C7(H7), N1(H1), C9(H9), C10(H10)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C1(H1A,H1B,H1C)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.679
_oxdiff_exptl_absorpt_empirical_full_min 0.570