Chiral molecular tweezers: synthesis and reactivity in asymmetric hydrogenation.
Lindqvist, Markus; Borre, Katja; Axenov, Kirill; Kótai, Bianka; Nieger, Martin; Leskelä, Markku; Pápai, Imre; Repo, Timo; Journal of the American Chemical Society 137 (2015) 4038–4041; doi:10.1021/ja512658m

data_4123408
_publ_section_title
;
 Chiral molecular tweezers: synthesis and reactivity in asymmetric
 hydrogenation.
;
_journal_issue                   12
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              4038
_journal_page_last               4041
_journal_paper_doi               10.1021/ja512658m
_journal_volume                  137
_journal_year                    2015
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C36 H24 B F10 N, C7 H8'
_chemical_formula_sum            'C43 H32 B F10 N'
_chemical_formula_weight         763.50
_chemical_name_systematic
;
 (S)-N-isopropyl-N-methyl-2-ammonium-2'-bis(pentafluorophenyl)-
hydroborate-1,1'-binaphthalen
;
_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'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.7066(1)
_cell_length_b                   18.4257(2)
_cell_length_c                   20.1642(2)
_cell_measurement_reflns_used    13175
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      76.8
_cell_measurement_theta_min      4.3
_cell_volume                     3606.39(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    Shelxtl.Plus
_computing_publication_material  publCIF
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    SHELXS-97
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 10.3953
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Agilent, SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'rotation in \w, 1\%'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            20757
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         76.829
_diffrn_reflns_theta_min         3.249
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.007
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70362
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_description       plates
_exptl_crystal_F_000             1568
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details
;
 Flack x determined using 3122 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
 Hooft's y parameter 0.03(3) (Hooft et al., J. Appl. Cryst. 2008).
;
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_extinction_coef       0.00075(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     505
_refine_ls_number_reflns         7561
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0342
_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^)+(0.0505P)^2^+0.4192P]
 where P=(Fo^2^+2Fc^2^)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0883
_refine_ls_wR_factor_ref         0.0899
_reflns_Friedel_coverage         0.781
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.986
_reflns_number_gt                7307
_reflns_number_total             7561
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja512658m_si_002.cif
_cod_data_source_block           les113_compound_S9
_cod_depositor_comments
'Adding full bibliography for 4123408--4123410.cif.'
_cod_original_cell_volume        3606.38(6)
_cod_database_code               4123408
_shelx_estimated_absorpt_t_min   0.689
_shelx_estimated_absorpt_t_max   0.970