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_4029555
_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         'C22 H F30 O2, C4 H12 N'
_chemical_formula_sum            'C26 H13 F30 N O2'
_chemical_formula_weight         941.37
_chemical_melting_point          236.0(10)
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                77.30(1)
_cell_angle_beta                 76.21(1)
_cell_angle_gamma                77.48(1)
_cell_formula_units_Z            2
_cell_length_a                   9.604(1)
_cell_length_b                   10.156(2)
_cell_length_c                   18.032(2)
_cell_measurement_reflns_used    22
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      13.59
_cell_measurement_theta_min      12.97
_cell_volume                     1641.1(4)
_computing_cell_refinement       SDP-plus
_computing_data_collection       SDP-plus
_computing_data_reduction        SDP-plus
_computing_molecular_graphics    XP
_computing_publication_material  CIFTAB
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'CAD4 Enraf-Nonius'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_av_sigmaI/netI    0.0265
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6253
_diffrn_reflns_theta_full        24.97
_diffrn_reflns_theta_max         24.97
_diffrn_reflns_theta_min         1.18
_diffrn_standards_decay_%        10
_diffrn_standards_interval_count 147
_diffrn_standards_interval_time  '4500 sec'
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.236
_exptl_absorpt_correction_T_max  0.9415
_exptl_absorpt_correction_T_min  0.9175
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details
'North A.C.T., Phillips D.C., Mathews F.S. (1968) Acta. Cryst. A24, 351-359.'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.905
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prizm
_exptl_crystal_F_000             924
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.28
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0080(12)
_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   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     537
_refine_ls_number_reflns         5760
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0784
_refine_ls_R_factor_gt           0.0461
_refine_ls_shift/su_max          0.045
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0695P)^2^+0.6709P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1202
_refine_ls_wR_factor_ref         0.1414
_reflns_number_gt                3767
_reflns_number_total             5760
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702513w-file006.cif
_cod_data_source_block           Compound_1a1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '235-237' was changed to '236.0(10)'
- the average value was taken and precision was
estimated.

'_symmetry_cell_setting' value 'Triclinic' changed to
'triclinic' 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.

'_exptl_absorpt_correction_type' value 'PSI-scan'
changed to 'psi-scan' 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 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_database_code               4029555