Asymmetric total synthesis of (−)-δ-lycorane
Wang, Junliang; Li, Jianneng; Shen, Xianwang; Dong, Cong; Lin, Jun; Wei, Kun; Organic Chemistry Frontiers 4 (2017) 1149–; doi:10.1039/C7QO00021A

data_1553726
_publ_section_title
;
 Asymmetric total synthesis of (&#x2212;)-\d-lycorane
;
_journal_issue                   6
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              1149
_journal_paper_doi               10.1039/C7QO00021A
_journal_volume                  4
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C16 H15 N O7'
_chemical_formula_sum            'C16 H15 N O7'
_chemical_formula_weight         333.29
_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
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-01-06 deposited with the CCDC.
2017-03-02 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   11.4884(5)
_cell_length_b                   11.9792(5)
_cell_length_c                   20.8251(8)
_cell_measurement_reflns_used    9888
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      70.16
_cell_measurement_theta_min      3.69
_cell_volume                     2866.0(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            21586
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         70.404
_diffrn_reflns_theta_min         4.246
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    1.047
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_description       plate
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.900
_exptl_crystal_size_mid          0.830
_exptl_crystal_size_min          0.070
_exptl_transmission_factor_max   0.7533
_exptl_transmission_factor_min   0.4443
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.125
_refine_ls_abs_structure_details
;
 Flack x determined using 2128 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         5304
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0527
_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^)+(0.1235P)^2^+0.6406P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1534
_refine_ls_wR_factor_ref         0.1545
_reflns_Friedel_coverage         0.740
_reflns_Friedel_fraction_full    0.972
_reflns_Friedel_fraction_max     0.944
_reflns_number_gt                5186
_reflns_number_total             5304
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7qo00021a2.cif
_cod_data_source_block           cu_yd_lj4a_0m
_cod_database_code               1553726
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.453
_shelx_estimated_absorpt_t_max   0.930
_shelx_res_checksum              28499
_shelx_hkl_checksum              92558