Synthesis of Concave and Vaulted 2<i>H</i>-Pyran-Fused BINOLs and Corresponding [5] and [7]-Oxa-helicenoids: Regioselective Cascade-Concerted Route and DFT Studies.
Kamble, Siddharth B.; Maliekal, Parimal J.; Dharpure, Pankaj D.; Badani, Purav M.; Karnik, Anil V.; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c00363

data_4038463
_publ_section_title
;
 Synthesis of Concave and Vaulted 2<i>H</i>-Pyran-Fused BINOLs and
 Corresponding [5] and [7]-Oxa-helicenoids: Regioselective
 Cascade-Concerted Route and DFT Studies.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c00363
_journal_year                    2020
_chemical_formula_sum            'C27 H18 N O4'
_chemical_formula_weight         420.42
_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'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.490(2)
_cell_length_b                   13.833(4)
_cell_length_c                   18.496(5)
_cell_measurement_reflns_used    3043
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      24.27
_cell_measurement_theta_min      2.20
_cell_volume                     1916.4(9)
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0756
_diffrn_reflns_av_unetI/netI     0.0763
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            21698
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.266
_diffrn_reflns_theta_min         1.838
_exptl_absorpt_coefficient_mu    0.098
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_description       'Rod Shape'
_exptl_crystal_F_000             876
_refine_diff_density_max         0.226
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.055
_refine_ls_abs_structure_details
;
 Flack x determined using 1249 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.8(9)
_refine_ls_extinction_coef       0.0095(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     281
_refine_ls_number_reflns         4728
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0752
_refine_ls_R_factor_gt           0.0480
_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^)+(0.0496P)^2^+0.1127P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1031
_refine_ls_wR_factor_ref         0.1174
_reflns_Friedel_coverage         0.752
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                3607
_reflns_number_total             4728
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c00363_si_003.cif
_cod_data_source_block           TRY_a
_cod_database_code               4038463
_shelx_shelxl_version_number     2014/7
_shelx_res_checksum              83948
_shelx_hkl_checksum              9243