Stepwise Preparation of All-cis 1,3,4-Trifluoro-2-phenylcyclohexane, Avoiding a Phenonium Intermediate.
Durie, Alastair J.; Fujiwara, Tomoya; Al-Maharik, Nawaf; Slawin, Alexandra M. Z.; O'Hagan, David; The Journal of organic chemistry 79 (2014) 8228–8233; doi:10.1021/jo501432x

data_4029882
_publ_section_title
;
 Stepwise Preparation of All-cis 1,3,4-Trifluoro-2-phenylcyclohexane,
 Avoiding a Phenonium Intermediate.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8228
_journal_page_last               8233
_journal_paper_doi               10.1021/jo501432x
_journal_volume                  79
_journal_year                    2014
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C12 H13 F3'
_chemical_formula_sum            'C12 H13 F3'
_chemical_formula_weight         214.23
_space_group_IT_number           33
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      33
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_formula_units_Z            4
_cell_length_a                   12.372(3)
_cell_length_b                   5.7322(13)
_cell_length_c                   14.470(4)
_cell_measurement_reflns_used    3148
_cell_measurement_temperature    173
_cell_measurement_theta_max      25.32
_cell_measurement_theta_min      3.26
_cell_volume                     1026.2(4)
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 rc13'
_computing_data_collection
'CrystalClear-SM Expert 2.0 rc13 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 rc13'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'Superflip (Palatinus, et al., 2007)'
_diffrn_ambient_temperature      173
_diffrn_detector_area_resol_mean 7.353
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Rigaku Mercury70'
_diffrn_measurement_method       \w
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            6307
_diffrn_reflns_point_group_measured_fraction_full 0.889
_diffrn_reflns_point_group_measured_fraction_max 0.880
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.331
_diffrn_reflns_theta_min         3.293
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.117
_exptl_absorpt_correction_T_max  0.993
_exptl_absorpt_correction_T_min  0.741
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.387
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             448.00
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.130
_refine_diff_density_min         -0.150
_refine_ls_abs_structure_details
'Parsons and Flack (2004), Acta Cryst. A60, s61. 513 quotients'
_refine_ls_abs_structure_Flack   -0.1(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_parameters     145
_refine_ls_number_reflns         1650
_refine_ls_number_restraints     1
_refine_ls_R_factor_gt           0.0394
_refine_ls_shift/su_max          0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[\s^2^(Fo^2^)+(0.0368P)^2^+0.1814P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0874
_reflns_number_gt                1395
_reflns_number_total             1650
_reflns_threshold_expression     F^2^>2.0\s(F^2^)
_cod_data_source_file            jo501432x_si_001.cif
_cod_data_source_block           4
_cod_depositor_comments          'Adding full bibliography for 4029882.cif.'
_cod_original_cell_volume        1026.1(4)
_cod_database_code               4029882