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_4123410
_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         'C14 H20 N, Cl'
_chemical_formula_sum            'C14 H20 Cl N'
_chemical_formula_weight         237.76
_chemical_name_systematic
;
 1-(1,2,3,4-tetrahydronaphthalen-1-yl)pyrrolidinium chloride
;
_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'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 102.354(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.3141(3)
_cell_length_b                   7.0195(4)
_cell_length_c                   11.3118(5)
_cell_measurement_reflns_used    88
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      2.5
_cell_volume                     644.88(5)
_computing_cell_refinement       EVALCCD
_computing_data_collection       Collect
_computing_data_reduction        EVALCCD
_computing_molecular_graphics    Shelxtl-Plus
_computing_publication_material  publCIF
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    SHELXS-97
_diffrn_ambient_temperature      123(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker-Nonius KappaCCD'
_diffrn_measurement_method       'rotation in \f and \w, 2\%'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0227
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10823
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_min         2.508
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.270
_exptl_absorpt_correction_T_max  0.9925
_exptl_absorpt_correction_T_min  0.8722
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_description       rods
_exptl_crystal_F_000             256
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.060
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 1289 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).

 Determination of absolute structure using Bayesian statistics 
 on Bijvoet differences (Hooft, Straver and Spek, 2008): 
 Hooft's y = -0.013(15) (Platon: Spek, 2009).
;
_refine_ls_abs_structure_Flack   -0.017(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     148
_refine_ls_number_reflns         2950
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0254
_refine_ls_R_factor_gt           0.0240
_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^)+(0.0311P)^2^+0.1159P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0589
_refine_ls_wR_factor_ref         0.0597
_reflns_Friedel_coverage         0.851
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2869
_reflns_number_total             2950
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja512658m_si_002.cif
_cod_data_source_block           les119_compound_17HCl
_cod_depositor_comments
'Adding full bibliography for 4123408--4123410.cif.'
_cod_database_code               4123410
_shelx_estimated_absorpt_t_min   0.919
_shelx_estimated_absorpt_t_max   0.984