Synthesis of Furan-Annelated BINOL Derivatives: Acid-Catalyzed Cyclization Induces Partial Racemization.
Octa-Smolin, Frescilia; van der Vight, Felix; Yadav, Rohan; Bhangu, Jasmine; Soloviova, Kateryna; Wölper, Christoph; Daniliuc, Constantin G.; Strassert, Cristian A.; Somnitz, Holger; Jansen, Georg; Niemeyer, Jochen; The Journal of organic chemistry 83 (2018) 14568–14587; doi:10.1021/acs.joc.8b02353

data_4035696
_publ_section_title
;
 Synthesis of Furan-Annelated BINOL Derivatives: Acid-Catalyzed
 Cyclization Induces Partial Racemization.
;
_journal_issue                   23
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              14568
_journal_page_last               14587
_journal_paper_doi               10.1021/acs.joc.8b02353
_journal_volume                  83
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_sum            'C84 H69 O15 P3'
_chemical_formula_weight         1411.30
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_cell_angle_alpha                115.368(2)
_cell_angle_beta                 105.172(2)
_cell_angle_gamma                95.372(2)
_cell_formula_units_Z            2
_cell_length_a                   16.2255(5)
_cell_length_b                   16.4626(5)
_cell_length_c                   17.2473(5)
_cell_measurement_reflns_used    9801
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      66.9006
_cell_measurement_theta_min      2.9038
_cell_volume                     3904.2(2)
_computing_cell_refinement       'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_data_collection
;

APEX3 v2016.1-0 (Bruker AXS Inc., 2016)
;
_computing_data_reduction        'SAINT V8.37A (Bruker AXS Inc., 2015)'
_computing_molecular_graphics    'XP (Sheldrick, 2014)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'MX mirror'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0771
_diffrn_reflns_av_unetI/netI     0.1085
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            51338
_diffrn_reflns_theta_full        67.14
_diffrn_reflns_theta_max         67.14
_diffrn_reflns_theta_min         2.90
_diffrn_source                   'Cu ImS'
_diffrn_source_type              'micro focus tube'
_exptl_absorpt_coefficient_mu    1.219
_exptl_absorpt_correction_T_max  0.92
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Bruker AXS (2014). SADABS, Version 2014/5, Bruker AXS Inc., Madison, Wisconsin,
USA.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1476
_exptl_crystal_size_max          0.172
_exptl_crystal_size_mid          0.158
_exptl_crystal_size_min          0.071
_refine_diff_density_max         0.878
_refine_diff_density_min         -0.610
_refine_ls_abs_structure_details
;

Flack x determined using 5079 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1993
_refine_ls_number_reflns         24296
_refine_ls_number_restraints     1255
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.1363
_refine_ls_R_factor_gt           0.1032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0653P)^2^+17.3999P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2197
_refine_ls_wR_factor_ref         0.2423
_reflns_number_gt                17822
_reflns_number_total             24296
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02353_si_003.cif
_cod_data_source_block           dan8947
_cod_database_code               4035696
_shelx_res_checksum              84136
_shelx_hkl_checksum              26112
_shelx_fab_checksum              13372