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_4128870
_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 rmad
_chemical_formula_moiety         'C25 H35 N O3'
_chemical_formula_sum            'C25 H35 N O3'
_chemical_formula_weight         397.54
_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     dual
_audit_creation_date             2019-07-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.2979(2)
_cell_length_b                   12.0524(4)
_cell_length_c                   23.9963(8)
_cell_measurement_reflns_used    9976
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      55.06
_cell_measurement_theta_min      3.19
_cell_volume                     2110.65(11)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      169.94
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0715
_diffrn_reflns_av_unetI/netI     0.0559
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            18279
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.043
_diffrn_reflns_theta_min         3.204
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.409
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1535 before and 0.0890 after correction. The Ratio of minimum to maximum transmission is 0.7709. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.251
_exptl_crystal_description       block
_exptl_crystal_F_000             864
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 1269 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(18)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     266
_refine_ls_number_reflns         4012
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0532
_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^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1465
_refine_ls_wR_factor_ref         0.1535
_reflns_Friedel_coverage         0.734
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                3495
_reflns_number_total             4012
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b05818_si_007.cif
_cod_data_source_block           mj19441_0m
_cod_database_code               4128870
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.968
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7), C9(H9), C12(H12), C16(H16), C22(H22)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C11(H11A,H11B), C13(H13A,H13B),
 C14(H14A,H14B), C15(H15A,H15B), C19(H19A,H19B), C23(H23A,H23B)
2.c X=CH2 refined with riding coordinates:
 C18(H18A,H18B)
2.d Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C24(H24A,H24B,H24C), C25(H25A,H25B,H25C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_shelx_res_checksum              75479
_shelx_hkl_checksum              61346
_olex2_submission_special_instructions 'No special instructions were received'