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_4033313
_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         'C14 H13 F3 N2 O2'
_chemical_formula_sum            'C14 H13 F3 N2 O2'
_chemical_formula_weight         298.26
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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                90
_cell_angle_beta                 104.030(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.9089(8)
_cell_length_b                   24.6306(18)
_cell_length_c                   9.2995(8)
_cell_measurement_reflns_used    2013
_cell_measurement_temperature    289.53(10)
_cell_measurement_theta_max      22.3070
_cell_measurement_theta_min      3.6830
_cell_volume                     2868.6(4)
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      289.53(10)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -17.00   12.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000   60.0000 29

  2 omega -102.00  -68.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  178.0000  -90.0000 34

  3 omega   35.00   89.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  178.0000   60.0000 54

  4 omega  -25.00   98.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   19.0000  120.0000 123
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0142489000
_diffrn_orient_matrix_UB_12      -0.0258338000
_diffrn_orient_matrix_UB_13      0.0324295000
_diffrn_orient_matrix_UB_21      -0.0117958000
_diffrn_orient_matrix_UB_22      -0.0119546000
_diffrn_orient_matrix_UB_23      -0.0714903000
_diffrn_orient_matrix_UB_31      0.0535679000
_diffrn_orient_matrix_UB_32      0.0042412000
_diffrn_orient_matrix_UB_33      -0.0042135000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            11177
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.021
_diffrn_reflns_theta_min         3.355
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.89075
_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    1.381
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.381
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         5639
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.1125
_refine_ls_R_factor_gt           0.0655
_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^)+(0.0709P)^2^+1.2005P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1571
_refine_ls_wR_factor_ref         0.1925
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3267
_reflns_number_total             5639
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01361_si_002.cif
_cod_data_source_block           mahaich_ome
_cod_database_code               4033313
_shelx_shelxl_version_number     2014/7
_reflns_odcompleteness_completeness 99.70
_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), C25(H25A,H25B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C2(H2A), C3(H3), C4(H4), C5(H5), N4(H4A), C16(H16), C17(H17),
 C18(H18), C19(H19)
2.c Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C26(H26A,H26B,H26C), C27(H27A,H27B,
 H27C)
;
_olex2_date_sample_data_collection 2017-05-04
_olex2_submission_special_instructions 'No special instructions were received'