Ir(III)-Catalyzed Aromatic C-H Bond Functionalization via Metal Carbene Migratory Insertion.
Xia, Ying; Liu, Zhen; Feng, Sheng; Zhang, Yan; Wang, Jianbo; The Journal of organic chemistry 80 (2014) 223–; doi:10.1021/jo5023102

data_4030329
_publ_section_title
;
 Ir(III)-Catalyzed Aromatic C-H Bond Functionalization via Metal Carbene
 Migratory Insertion.
;
_journal_issue                   1
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              223
_journal_paper_doi               10.1021/jo5023102
_journal_volume                  80
_journal_year                    2014
_chemical_formula_moiety         'C16 H21 N O5'
_chemical_formula_sum            'C16 H21 N O5'
_chemical_formula_weight         307.34
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2014-04-17
_audit_creation_method
;
  Olex2 1.2
  (compiled Apr 23 2013 17:54:37, GUI svn.r4466)
;
_cell_angle_alpha                90
_cell_angle_beta                 113.000(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   17.4149(12)
_cell_length_b                   9.7931(4)
_cell_length_c                   20.9100(11)
_cell_measurement_reflns_used    4132
_cell_measurement_temperature    180.01(10)
_cell_measurement_theta_max      28.4730
_cell_measurement_theta_min      3.5720
_cell_volume                     3282.6(4)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement
;
XL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790'
_diffrn_ambient_temperature      180.01(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.9869
_diffrn_measured_fraction_theta_max 0.8244
_diffrn_measurement_details
;
  1 omega  -66.00   43.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       10.8579  -77.0000  -30.0000 109

  2 omega   35.00   98.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       10.8579  178.0000  150.0000 63
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0022774000
_diffrn_orient_matrix_UB_12      -0.0102294000
_diffrn_orient_matrix_UB_13      -0.0327998000
_diffrn_orient_matrix_UB_21      0.0388938000
_diffrn_orient_matrix_UB_22      0.0345020000
_diffrn_orient_matrix_UB_23      0.0118903000
_diffrn_orient_matrix_UB_31      0.0209989000
_diffrn_orient_matrix_UB_32      -0.0628238000
_diffrn_orient_matrix_UB_33      0.0118669000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0566
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            13226
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         2.923
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.092
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67508
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.269
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     407
_refine_ls_number_reflns         6416
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0510
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0464P)^2^+1.1147P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1089
_refine_ls_wR_factor_ref         0.1265
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4343
_reflns_number_total             6416
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5023102_si_001.cif
_cod_data_source_block           exp_3344
_cod_depositor_comments
'Adding full bibliography for 4030327--4030329.cif.'
_cod_original_cell_volume        3282.6(3)
_cod_database_code               4030329
_chemical_oxdiff_formula         'C15 H21 O3 N1'
_reflns_odcompleteness_completeness 98.69
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_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 Ternary CH refined with riding coordinates:
 C7(H7), C23(H23)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C18(H18), C19(H19), C20(H20), C21(H21),
 N1(H1), N2(H2A)
2.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C11(H11A,H11B,H11C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C16(H16A,H16B,H16C), C25(H25A,H25B,H25C), C27(H27A,H27B,H27C), C30(H30A,
 H30B,H30C), C31(H31A,H31B,H31C), C32(H32A,H32B,H32C)
;
_shelx_estimated_absorpt_t_max   0.991
_shelx_estimated_absorpt_t_min   0.982
_shelxl_version_number           2013-3