(2-Fluoroallyl)boration of ketones with (2-fluoroallyl)boronates.
Novikov, Maxim A.; Bobrova, Angelina; Mezentsev, Igor; Medvedev, Michael G.; Tomilov, Yury V.; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.9b03445

data_4038327
_publ_section_title
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 (2-Fluoroallyl)boration of ketones with (2-fluoroallyl)boronates.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03445
_journal_year                    2020
_chemical_formula_moiety         'C24 H20 F N O4'
_chemical_formula_sum            'C24 H20 F N O4'
_chemical_formula_weight         405.41
_chemical_name_systematic
'4-fluoro-2,3-diphenylpent-4-en-2-yl 4-nitrobenzoate'
_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
_audit_creation_date             2020-03-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.0732(13)
_cell_length_b                   11.111(2)
_cell_length_c                   29.291(6)
_cell_measurement_reflns_used    630
_cell_measurement_temperature    120
_cell_measurement_theta_max      20.51
_cell_measurement_theta_min      2.30
_cell_volume                     1976.5(7)
_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    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      120
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.1180
_diffrn_reflns_av_unetI/netI     0.1318
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            10861
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.016
_diffrn_reflns_theta_max         25.016
_diffrn_reflns_theta_min         1.960
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0819 before and 0.0728 after correction. The Ratio of minimum to maximum transmission is 0.8217. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_description       needle
_exptl_crystal_F_000             848
_exptl_crystal_recrystallization_method 'from cyclohexane'
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -1(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.979
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3486
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.979
_refine_ls_R_factor_all          0.1135
_refine_ls_R_factor_gt           0.0554
_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^)+(0.0284P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1233
_reflns_Friedel_coverage         0.702
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2165
_reflns_number_total             3486
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo9b03445_si_003.cif
_cod_data_source_block           data
_cod_database_code               4038327
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.980
_shelx_estimated_absorpt_t_min   0.971
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 2(2)
 -1(2)
2. 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
3.a Ternary CH refined with riding coordinates:
 C4(H4)
3.b Aromatic/amide H refined with riding coordinates:
 C24(H24), C20(H20), C11(H11), C22(H22), C23(H23), C21(H21), C12(H12),
 C14(H14), C15(H15), C30(H30), C26(H26), C27(H27), C29(H29), C28(H28)
3.c X=CH2 refined with riding coordinates:
 C1(H1A,H1B)
3.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C)
;
_olex2_submission_original_sample_id n2203b
_olex2_submission_special_instructions 'No special instructions were received'