Atropo- and Diastereoselective Construction of Tetracyclic Biphenylazepinium Salts Derived from Aminoalcohols: Use as Catalysts in Enantioselective Asymmetric Epoxidation.
Bulman Page, Philip C.; Pearce, Christopher A.; Chan, Yohan; Parker, Phillip; Buckley, Benjamin R.; Rassias, Gerasimos A.; Elsegood, Mark R. J.; The Journal of organic chemistry 80 (2015) 8036–8045; doi:10.1021/acs.joc.5b01157

data_4031334
_publ_section_title
;
 Atropo- and Diastereoselective Construction of Tetracyclic
 Biphenylazepinium Salts Derived from Aminoalcohols: Use as Catalysts in
 Enantioselective Asymmetric Epoxidation.
;
_journal_issue                   16
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              8036
_journal_page_last               8045
_journal_paper_doi               10.1021/acs.joc.5b01157
_journal_volume                  80
_journal_year                    2015
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C24 H23 N O'
_chemical_formula_sum            'C24 H23 N O'
_chemical_formula_weight         341.43
_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   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 98.4207(7)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.5648(4)
_cell_length_b                   9.8551(5)
_cell_length_c                   11.1777(5)
_cell_measurement_reflns_used    4517
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      30.51
_cell_measurement_theta_min      2.40
_cell_volume                     933.30(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX 2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL and local programs'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX 2 CCD diffractometer'
_diffrn_measurement_method       '\w rotation with narrow frames'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11151
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.561
_diffrn_reflns_theta_min         1.842
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_correction_T_min  0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2007/2, Sheldrick, G.M., (2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             364
_exptl_crystal_size_max          0.520
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.360
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
; 
 Flack x determined using 2051 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.7(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         5541
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0490
_refine_ls_R_factor_gt           0.0442
_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^)+(0.0692P)^2^+0.0431P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1144
_refine_ls_wR_factor_ref         0.1185
_reflns_Friedel_coverage         0.841
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.932
_reflns_number_gt                4987
_reflns_number_total             5541
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo5b01157_si_002.cif
_cod_data_source_block           27
_cod_depositor_comments
'Adding full bibliography for 4031333--4031334.cif.'
_cod_database_code               4031334
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.963
_shelx_estimated_absorpt_t_max   0.974
_shelx_res_checksum              50289
_shelx_hkl_checksum              57367