A Domino Azidation/C-H Amination Approach toward Trifluoromethyl Substituted Imidazoles.
Ma, Haichao; Zhang, Xiaoyan; Chen, Liangliang; Yu, Wei; The Journal of organic chemistry 82 (2017) 11841–11847; doi:10.1021/acs.joc.7b01361

data_4033312
_publ_section_title
;
 A Domino Azidation/C-H Amination Approach toward Trifluoromethyl
 Substituted Imidazoles.
;
_journal_issue                   22
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              11841
_journal_page_last               11847
_journal_paper_doi               10.1021/acs.joc.7b01361
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C13 H10 Br F3 N2 O2'
_chemical_formula_sum            'C13 H10 Br F3 N2 O2'
_chemical_formula_weight         363.14
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-05-24
_audit_creation_method
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Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
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_cell_angle_alpha                85.354(7)
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_cell_angle_gamma                64.817(9)
_cell_formula_units_Z            2
_cell_length_a                   8.0597(7)
_cell_length_b                   8.0602(7)
_cell_length_c                   12.2760(10)
_cell_measurement_reflns_used    1089
_cell_measurement_temperature    291.9(3)
_cell_measurement_theta_max      24.9610
_cell_measurement_theta_min      4.1250
_cell_volume                     702.40(12)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      291.9(3)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega   -2.00   24.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000   90.0000 26

  2 omega    5.00   57.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000  -60.0000 52

  3 omega  -48.00   38.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000 -180.0000 86

  4 omega  -49.00   47.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -77.0000   90.0000 96

  5 omega   -1.00   25.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   57.0000   90.0000 26

  6 omega  -40.00   46.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000  -60.0000 86
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0320421000
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_diffrn_orient_matrix_UB_13      -0.0580732000
_diffrn_orient_matrix_UB_21      0.0473089000
_diffrn_orient_matrix_UB_22      -0.0938741000
_diffrn_orient_matrix_UB_23      0.0123206000
_diffrn_orient_matrix_UB_31      -0.0815693000
_diffrn_orient_matrix_UB_32      -0.0131827000
_diffrn_orient_matrix_UB_33      -0.0000416000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0445
_diffrn_reflns_av_unetI/netI     0.0832
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4386
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.018
_diffrn_reflns_theta_min         3.633
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.965
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55390
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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    1.717
_exptl_crystal_description
;
;
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.427
_refine_diff_density_min         -0.670
_refine_diff_density_rms         0.125
_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     191
_refine_ls_number_reflns         2742
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.1011
_refine_ls_R_factor_gt           0.0647
_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^)+(0.0762P)^2^+0.1683P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1434
_refine_ls_wR_factor_ref         0.1777
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1767
_reflns_number_total             2742
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01361_si_003.cif
_cod_data_source_block           mahch_pbr
_cod_original_cell_volume        702.40(11)
_cod_database_code               4033312
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.69
_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 C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C5(H5), C6(H6)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C)
;
_olex2_date_sample_data_collection 2017-05-03
_olex2_submission_special_instructions 'No special instructions were received'