Diverse Trifluoromethyl Heterocycles from a Single Precursor
Mark A. Honey; Raffaele Pasceri; William Lewis; Christopher J. Moody; Journal of Organic Chemistry 77 (2012) 1396–1405; doi:10.1021/jo202201w

data_4026919
_publ_section_title
;
 Diverse Trifluoromethyl Heterocycles from a Single Precursor
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1396
_journal_page_last               1405
_journal_paper_doi               10.1021/jo202201w
_journal_volume                  77
_journal_year                    2012
_chemical_formula_moiety         'C13 H9 Br F3 N O3'
_chemical_formula_sum            'C13 H9 Br F3 N O3'
_chemical_formula_weight         364.12
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_method           'enCIFer editing of SHELXL-97 created file'
_cell_angle_alpha                90.00
_cell_angle_beta                 111.752(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.6332(4)
_cell_length_b                   7.9560(2)
_cell_length_c                   15.6028(4)
_cell_measurement_reflns_used    10828
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      74.40
_cell_measurement_theta_min      4.09
_cell_volume                     1341.27(8)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    ' ? '
_computing_publication_material  'enCIFer(Allen et al.,2004);PLATON(Spek,2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution
;
  Olex2 1.1
  (compiled 2011.09.07 svn.r1971, GUI svn.r3853)
;
_diffrn_ambient_temperature      90(2)
_diffrn_detector_area_resol_mean 10.3613
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'SuperNova (Cu) x-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0111
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            18843
_diffrn_reflns_theta_full        67.50
_diffrn_reflns_theta_max         74.57
_diffrn_reflns_theta_min         4.09
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.638
_exptl_absorpt_correction_T_max  1.188
_exptl_absorpt_correction_T_min  0.352
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.803
_exptl_crystal_description       plate
_exptl_crystal_F_000             720
_exptl_crystal_size_max          0.3699
_exptl_crystal_size_mid          0.2290
_exptl_crystal_size_min          0.0198
_refine_diff_density_max         0.751
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.155
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2713
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.155
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0326
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0216P)^2^+4.6276P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0863
_reflns_number_gt                2567
_reflns_number_total             2713
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            jo202201w_si_002_5b.cif
_cod_data_source_block           RPCJMB
_cod_original_cell_volume        1341.27(7)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4026919
_nottingham_internal_coll_name   RPCJMB
_nottingham_internal_coll_number 10484
_nottingham_internal_coll_client RP/CJM
_nottingham_internal_coll_type   custom
_nottingham_internal_coll_frame_time '12.0000 and 3.0000'
_nottingham_internal_coll_frame_width 1.0000
_nottingham_internal_coll_frame_method '\w scans'
_nottingham_internal_coll_user   WL
_nottingham_internal_coll_date   10/6/2011
_nottingham_internal_process_user WL
_nottingham_internal_process_date 13/06/2011
_nottingham_internal_solution_user WL
_nottingham_internal_solution_date 13/6/2011
_nottingham_internal_refinement_user WL
_nottingham_internal_refinement_date 11/10/2011
_nottingham_internal_validation_user WL
_nottingham_internal_validation_date 12/10/2011
_nottingham_internal_archive_date 12/10/2011