Chiral <i>gem</i>-difluoroalkyl reagents: <i>gem</i>-difluoroalkyl propargylic borons and <i>gem</i>-difluoroalkyl α-allenols.
Zou, Hui-Na; Huang, Meng-Lin; Huang, Ming-Yao; Su, Yu-Xuan; Zhang, Jing-Wei; Zhang, Xin-Yu; Zhu, Shou-Fei; Chemical science 14 (2023) 9186–9190; doi:10.1039/d3sc03266c

data_1569654
_publ_section_title
;
 Chiral <i>gem</i>-difluoroalkyl reagents: <i>gem</i>-difluoroalkyl
 propargylic borons and <i>gem</i>-difluoroalkyl &#x3b1;-allenols.
;
_journal_issue                   34
_journal_name_full               'Chemical science'
_journal_page_first              9186
_journal_page_last               9190
_journal_paper_doi               10.1039/d3sc03266c
_journal_volume                  14
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C19 H21 B Cl F2 N'
_chemical_formula_sum            'C19 H21 B Cl F2 N'
_chemical_formula_weight         347.63
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2022-07-03
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2023-03-04 deposited with the CCDC.	2023-08-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.909(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.2271(5)
_cell_length_b                   10.3968(7)
_cell_length_c                   21.4304(11)
_cell_measurement_reflns_used    7166
_cell_measurement_temperature    113.15
_cell_measurement_theta_max      29.9840
_cell_measurement_theta_min      1.9070
_cell_volume                     1819.75(19)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      113.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.912
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w   -115.00  65.00   1.00    1.00    --  -25.00  45.00   0.00  180
  2  \w   -115.00  35.00   1.00    1.00    --  -25.00  45.00  90.00  150
  3  \w   -115.00   5.00   1.00    1.00    --  -25.00  45.00 180.00  120
;
_diffrn_measurement_device       'abstract diffractometer'
_diffrn_measurement_device_type  'Rigaku mm007 Saturn70'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0775146000
_diffrn_orient_matrix_UB_12      -0.0003075000
_diffrn_orient_matrix_UB_13      0.0184964000
_diffrn_orient_matrix_UB_21      0.0390295000
_diffrn_orient_matrix_UB_22      -0.0048331000
_diffrn_orient_matrix_UB_23      -0.0276756000
_diffrn_orient_matrix_UB_31      0.0031714000
_diffrn_orient_matrix_UB_32      0.0680499000
_diffrn_orient_matrix_UB_33      -0.0018556000
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_av_unetI/netI     0.1339
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.912
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            22992
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.857
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.942
_diffrn_reflns_theta_min         1.914
_diffrn_source                   'rotating anode'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73732
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details
;
 Flack x determined using 1617 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(7)
_refine_ls_extinction_coef       0.0055(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     456
_refine_ls_number_reflns         11704
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1428
_refine_ls_R_factor_gt           0.0677
_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^)+(0.0491P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1228
_refine_ls_wR_factor_ref         0.1648
_reflns_Friedel_coverage         0.795
_reflns_Friedel_fraction_full    0.974
_reflns_Friedel_fraction_max     0.796
_reflns_number_gt                6269
_reflns_number_total             11704
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc03266c3.cif
_cod_data_source_block           r20220701b
_cod_depositor_comments          'Adding full bibliography for 1569654.cif.'
_cod_database_code               1569654
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C11 H10 N O'
_shelx_estimated_absorpt_t_max   0.962
_shelx_estimated_absorpt_t_min   0.949
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 B2-H2B = B2-H2A = B1-H1A = B1-H1B
 1 with sigma of 0.01
 H2B-H2A = H1A-H1B
 1.6 with sigma of 0.01
3.a Ternary CH refined with riding coordinates:
 C8(H8), C27(H27)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16), C21(H21), C22(H22), C24(H24), C25(H25), C31(H31), C32(H32), C33(H33),
  C34(H34), C35(H35)
3.c Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C36(H36A,H36B,
 H36C), C37(H37A,H37B,H37C), C38(H38A,H38B,H38C)
;
_shelx_res_checksum              9286
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.527
_oxdiff_exptl_absorpt_empirical_full_min 0.471