Recyclable Trifluoromethylation Reagents from Fluoroform
Geri, Jacob B.; Szymczak, Nathaniel K.; Journal of the American Chemical Society  (2017) –; doi:10.1021/jacs.7b05408

data_4126282
_publ_section_title
;
 Recyclable Trifluoromethylation Reagents from Fluoroform
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b05408
_journal_year                    2017
_chemical_formula_moiety         'C12 H24 K O6, C13 H25 B3 N3'
_chemical_formula_sum            'C25 H49 B3 K N3 O6'
_chemical_formula_weight         559.20
_chemical_name_systematic        K(18-crown-6)Me6B3N3(CH2C6H5)
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2016-03-04
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.135(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.7712(2)
_cell_length_b                   22.1274(4)
_cell_length_c                   15.9338(11)
_cell_measurement_reflns_used    25430
_cell_measurement_temperature    225
_cell_measurement_theta_max      68.30
_cell_measurement_theta_min      2.80
_cell_volume                     3092.5(2)
_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    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      225
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Rigaku Saturn70 CCD'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            47416
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         68.236
_diffrn_reflns_theta_min         3.418
_exptl_absorpt_coefficient_mu    1.830
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.813
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.201
_exptl_crystal_description       plate
_exptl_crystal_F_000             1208
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.231
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       0.0064(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     350
_refine_ls_number_reflns         5636
_refine_ls_number_restraints     27
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0679
_refine_ls_R_factor_gt           0.0668
_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^)+(0.1013P)^2^+2.6826P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1814
_refine_ls_wR_factor_ref         0.1829
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5447
_reflns_number_total             5665
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja7b05408_si_001.cif
_cod_data_source_block           5
_cod_database_code               4126282
_shelx_estimated_absorpt_t_max   1.000
_shelx_estimated_absorpt_t_min   0.668
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 C12, C34, C36, C37, C38, B32
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.005
 N8, N9, N10, C20, C30, B13, B22, B32
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3.a Secondary CH2 refined with riding coordinates:
 C34(H34A,H34B), C11(H11A,H11B), C14(H14A,H14B), C15(H15A,H15B), C17(H17A,
 H17B), C18(H18A,H18B), C19(H19A,H19B), C23(H23A,H23B), C24(H24A,H24B),
 C25(H25A,H25B), C29(H29A,H29B), C31(H31A,H31B), C33(H33A,H33B)
3.b Aromatic/amide H refined with riding coordinates:
 C28(H28), C35(H35), C36(H36), C37(H37), C38(H38)
3.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C26(H26A,H26B,
 H26C), C27(H27A,H27B,H27C), C30(H30A,H30B,H30C)
;
_shelx_res_checksum              23498
_shelx_hkl_checksum              78476
_shelx_shelxl_version_number     2014/7
_olex2_submission_original_sample_id K(18-crown-6)Me6B3N3(CH2C6H5)
_olex2_submission_special_instructions 'No special instructions were received'