N-C Axially Chiral Compounds with an ortho-Fluoro Substituent and Steric Discrimination between Hydrogen and Fluorine Atoms Based on a Diastereoselective Model Reaction.
Iida, Asumi; Matsuoka, Mizuki; Hasegawa, Hiroshi; Vanthuyne, Nicolas; Farran, Daniel; Roussel, Christian; Kitagawa, Osamu; The Journal of organic chemistry 84 (2019) 3169–3175; doi:10.1021/acs.joc.8b03043

data_4033898
_publ_section_title
;
 N-C Axially Chiral Compounds with an ortho-Fluoro Substituent and Steric
 Discrimination between Hydrogen and Fluorine Atoms Based on a
 Diastereoselective Model Reaction.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3169
_journal_page_last               3175
_journal_paper_doi               10.1021/acs.joc.8b03043
_journal_volume                  84
_journal_year                    2019
_chemical_formula_sum            'C19 H19 F N2 O'
_chemical_formula_weight         310.36
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                90
_cell_angle_beta                 105.803(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.0214(8)
_cell_length_b                   17.6814(12)
_cell_length_c                   8.6332(5)
_cell_measurement_reflns_used    256
_cell_measurement_temperature    170.(2)
_cell_measurement_theta_max      24.9465
_cell_measurement_theta_min      3.8460
_cell_volume                     1618.80(19)
_computing_cell_refinement       'APEX3 v2017.3-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 833)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      170.(2)
_diffrn_detector_area_resol_mean 7.3910
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_radiation_monochromator  'multilayered confocal mirror'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0542
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            18059
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         2.71
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.89
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.402
_exptl_crystal_size_mid          0.126
_exptl_crystal_size_min          0.109
_refine_diff_density_max         0.266
_refine_diff_density_min         -0.219
_refine_ls_extinction_coef       0.021(4)
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     339
_refine_ls_number_reflns         2855
_refine_ls_number_restraints     1134
_refine_ls_restrained_S_all      1.106
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0530
_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^)+(0.0808P)^2^+0.6958P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1524
_refine_ls_wR_factor_ref         0.1657
_reflns_number_gt                2276
_reflns_number_total             2855
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b03043_si_001.cif
_cod_data_source_block           ssss
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4033898
_shelx_res_checksum              65552
_shelx_hkl_checksum              54163