Pentakis(trifluoromethyl)phenyl, a sterically crowded and electron-withdrawing group: synthesis and acidity of pentakis(trifluoromethyl)benzene, -toluene, -phenol, and -aniline.
Kütt, Agnes; Movchun, Valeria; Rodima, Toomas; Dansauer, Timo; Rusanov, Eduard B.; Leito, Ivo; Kaljurand, Ivari; Koppel, Juta; Pihl, Viljar; Koppel, Ivar; Ovsjannikov, Gea; Toom, Lauri; Mishima, Masaaki; Medebielle, Maurice; Lork, Enno; Röschenthaler, Gerd-Volker; Koppel, Ilmar A.; Kolomeitsev, Alexander A.; The Journal of organic chemistry 73 (2008) 2607–2620; doi:10.1021/jo702513w

data_4029556
_publ_section_title
;
 Pentakis(trifluoromethyl)phenyl, a sterically crowded and
 electron-withdrawing group: synthesis and acidity of
 pentakis(trifluoromethyl)benzene, -toluene, -phenol, and -aniline.
;
_journal_issue                   7
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              2607
_journal_page_last               2620
_journal_paper_doi               10.1021/jo702513w
_journal_volume                  73
_journal_year                    2008
_chemical_formula_moiety         'C14 F15 N2, C8 H20 N'
_chemical_formula_sum            'C22 H20 F15 N3'
_chemical_formula_weight         611.41
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 111.180(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   25.148(4)
_cell_length_b                   11.8370(10)
_cell_length_c                   18.256(2)
_cell_measurement_reflns_used    44
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      12.509
_cell_measurement_theta_min      3.787
_cell_volume                     5067.3(11)
_computing_cell_refinement       'Siemens XSCANS'
_computing_data_collection       'Siemens XSCANS'
_computing_data_reduction        'Siemens XSCANS'
_computing_molecular_graphics    'Diamond, Crystal Impact'
_computing_publication_material  'Siemens SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       '2\q/\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'normal-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_sigmaI/netI    0.0344
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12484
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.82
_diffrn_standards_decay_%        'random variation +/-2.0'
_diffrn_standards_interval_count 197
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2464
_exptl_crystal_size_max          1.0
_exptl_crystal_size_mid          0.9
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.00091(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    refU
_refine_ls_matrix_type           full
_refine_ls_number_parameters     424
_refine_ls_number_reflns         5742
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0372
_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^)+(0.0407P)^2^+3.3119P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0939
_refine_ls_wR_factor_ref         0.1015
_reflns_number_gt                4592
_reflns_number_total             5742
_reflns_threshold_expression     >2\s(I)
_cod_data_source_file            jo702513w-file007.cif
_cod_data_source_block           Compound_7a
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4029556