Developing organoboranes as phase transfer catalysts for nucleophilic fluorination using CsF
Kirschner, Sven; Peters, Matthew; Yuan, Kang; Uzelac, Marina; Ingleson, Michael J.; Chemical Science  (2022) –; doi:10.1039/D2SC00303A

data_1566365
_publ_section_title
;
 Developing organoboranes as phase transfer catalysts for nucleophilic
 fluorination using CsF
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D2SC00303A
_journal_year                    2022
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C42 H71 B2 Cs2 F2 N3'
_chemical_formula_sum            'C42 H71 B2 Cs2 F2 N3'
_chemical_formula_weight         943.45
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-10-19
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6403)
;
_audit_update_record
;
2021-10-19 deposited with the CCDC.	2022-02-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5055(10)
_cell_length_b                   17.6861(18)
_cell_length_c                   24.528(2)
_cell_measurement_reflns_used    9284
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      25.36
_cell_measurement_theta_min      2.30
_cell_volume                     4557.3(7)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0913
_diffrn_reflns_av_unetI/netI     0.0225
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            269071
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.411
_diffrn_reflns_theta_min         2.255
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.638
_exptl_absorpt_correction_T_max  0.4288
_exptl_absorpt_correction_T_min  0.3645
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1084 before and 0.0956 after correction. The Ratio of minimum to maximum transmission is 0.8500. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_description       plate
_exptl_crystal_F_000             1928
_exptl_crystal_size_max          0.168
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.064
_refine_diff_density_max         1.026
_refine_diff_density_min         -0.620
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 3476 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.015(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     469
_refine_ls_number_reflns         8401
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0235
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0226P)^2^+4.9956P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0552
_refine_ls_wR_factor_ref         0.0560
_reflns_Friedel_coverage         0.793
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                8038
_reflns_number_total             8401
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2sc00303a2.cif
_cod_data_source_block           mi20004
_cod_original_cell_volume        4557.4(8)
_cod_database_code               1566365
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.902
_shelx_estimated_absorpt_t_min   0.770
_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.a Ternary CH refined with riding coordinates:
 C10(H10), C9(H9), C11(H11), C27(H27), C32(H32), C13(H13), C29(H29), C31(H31),
 C1(H1), C5(H5), C23(H23), C19(H19)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C14(H14A,H14B), C30(H30A,H30B), C28(H28A,H28B), C8(H8A,H8B),
 C26(H26A,H26B), C7(H7A,H7B), C24(H24A,H24B), C6(H6A,H6B), C3(H3A,H3B), C2(H2A,
 H2B), C4(H4A,H4B), C22(H22A,H22B), C25(H25A,H25B), C21(H21A,H21B), C20(H20A,
 H20B)
2.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C16(H16A,H16B,H16C), C33(H33A,H33B,
 H33C), C42(H42A,H42B,H42C), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C), C38(H38A,
 H38B,H38C), C40(H40A,H40B,H40C)
;
_shelx_res_checksum              59723
_olex2_submission_special_instructions 'No special instructions were received'