Asymmetric Total Synthesis of Arcutinidine, Arcutinine, and Arcutine.
Zhou, Shupeng; Xia, Kaifu; Leng, Xuebing; Li, Ang; Journal of the American Chemical Society 141 (2019) 13718–13723; doi:10.1021/jacs.9b05818

data_4128875
_publ_section_title
;
 Asymmetric Total Synthesis of Arcutinidine, Arcutinine, and Arcutine.
;
_journal_issue                   35
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              13718
_journal_page_last               13723
_journal_paper_doi               10.1021/jacs.9b05818
_journal_volume                  141
_journal_year                    2019
_chemical_absolute_configuration ad
_chemical_formula_sum            'C20 H28 N O2.5'
_chemical_formula_weight         322.43
_space_group_crystal_system      orthorhombic
_space_group_IT_number           20
_space_group_name_Hall           'C 2c 2'
_space_group_name_H-M_alt        'C 2 2 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.1921(3)
_cell_length_b                   15.8104(4)
_cell_length_c                   17.6415(4)
_cell_measurement_reflns_used    7957
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      140.319
_cell_measurement_theta_min      9.160
_cell_volume                     3400.61(14)
_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-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.997
_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  0.0765
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            20543
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         67.499
_diffrn_reflns_theta_min         4.580
_exptl_absorpt_coefficient_mu    0.647
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1400
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.030
_refine_ls_abs_structure_details
; 
 Flack x determined using 1137 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.08(15)
_refine_ls_extinction_coef       0.0017(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3055
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0449
_refine_ls_R_factor_gt           0.0398
_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^)+(0.0445P)^2^+0.9076P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1024
_reflns_Friedel_coverage         0.780
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.996
_reflns_number_gt                2796
_reflns_number_total             3055
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b05818_si_004.cif
_cod_data_source_block           d8v19373
_cod_original_formula_sum        'C20 H28 N O2.50'
_cod_database_code               4128875
_shelx_estimated_absorpt_t_min   0.892
_shelx_estimated_absorpt_t_max   0.938
_shelxl_version_number           2013-4
_shelx_res_checksum              64830
_shelx_hkl_checksum              36821