Enantioselective Total Synthesis of (+)-Arboridinine.
Zhang, Zhen; Xie, Sujun; Cheng, Bin; Zhai, Hongbin; Li, Yun; Journal of the American Chemical Society 141 (2019) 7147–7154; doi:10.1021/jacs.9b02362

data_4128148
_publ_section_title
;
 Enantioselective Total Synthesis of (+)-Arboridinine.
;
_journal_issue                   17
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              7147
_journal_page_last               7154
_journal_paper_doi               10.1021/jacs.9b02362
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C19 H22 N2 O'
_chemical_formula_sum            'C19 H23 N2 O'
_chemical_formula_weight         295.39
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-02-14
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                85.937(5)
_cell_angle_beta                 89.698(4)
_cell_angle_gamma                85.953(4)
_cell_formula_units_Z            4
_cell_length_a                   8.1557(4)
_cell_length_b                   11.7870(7)
_cell_length_c                   16.3493(9)
_cell_measurement_reflns_used    3041
_cell_measurement_temperature    291.59(10)
_cell_measurement_theta_max      69.5480
_cell_measurement_theta_min      5.4100
_cell_volume                     1563.82(15)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      291.59(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w     -9.00  70.00   1.00    2.00    --    0.00  38.00 -60.00   79
  2  \w     62.00 120.00   1.00    4.00    --   54.00  57.00 -60.00   58
  3  \w     75.00 103.00   1.00    4.00    --   54.00  57.00-150.00   28
  4  \w    101.00 127.00   1.00    6.00    --  108.00 111.00-180.00   26
  5  \w     47.00 175.00   1.00    6.00    --  108.00  12.00 -90.00  128
  6  \w     89.00 115.00   1.00    6.00    --  108.00-111.00 -90.00   26
  7  \w     55.00 116.00   1.00    6.00    --  108.00 -77.00-150.00   61
  8  \w     58.00 101.00   1.00    6.00    --  108.00-111.00-150.00   43
  9  \w     37.00 133.00   1.00    6.00    --  108.00 -38.00-150.00   96
 10  \w     43.00 104.00   1.00    6.00    --  108.00-111.00  30.00   61
 11  \w     82.00 107.00   1.00    6.00    --  108.00-107.00  87.00   25
 12  \w     52.00 125.00   1.00    6.00    --  108.00 -50.00 120.00   73
 13  \w     48.00 120.00   1.00    4.00    --   54.00  57.00  60.00   72
 14  \w     93.00 167.00   1.00    6.00    --  108.00  63.00 150.00   74
 15  \w    152.00 178.00   1.00    6.00    --  108.00 111.00  90.00   26
 16  \w    100.00 129.00   1.00    6.00    --  108.00 111.00  90.00   29
 17  \w     75.00 103.00   1.00    6.00    --  108.00 178.00 120.00   28
 18  \w     34.00 103.00   1.00    4.00    --   54.00  57.00   0.00   69
 19  \w     38.00 133.00   1.00    6.00    --  108.00 -38.00   0.00   95
 20  \w     47.00 136.00   1.00    6.00    --  108.00 -77.00  30.00   89
 21  \w     27.00 107.00   1.00    4.00    --   54.00-125.00  90.00   80
 22  \w     20.00  56.00   1.00    4.00    --   54.00 -57.00  60.00   36
 23  \w    -15.00  51.00   1.00    4.00    --   54.00 -57.00 150.00   66
 24  \w    -23.00  20.00   1.00    2.00    --    0.00 -57.00 150.00   43
 25  \w      6.00  71.00   1.00    4.00    --   54.00 -99.00 -90.00   65
 26  \w    -61.00 -25.00   1.00    2.00    --    0.00 -57.00 150.00   36
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0518093000
_diffrn_orient_matrix_UB_12      -0.0821606000
_diffrn_orient_matrix_UB_13      -0.0661883000
_diffrn_orient_matrix_UB_21      -0.0089524000
_diffrn_orient_matrix_UB_22      -0.1021134000
_diffrn_orient_matrix_UB_23      0.0637233000
_diffrn_orient_matrix_UB_31      -0.1819218000
_diffrn_orient_matrix_UB_32      -0.0087505000
_diffrn_orient_matrix_UB_33      -0.0219590000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10237
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         69.714
_diffrn_reflns_theta_min         3.769
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.607
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84028
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.255
_exptl_crystal_description       block
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.307
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.0017(5)
_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   1.108
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     420
_refine_ls_number_reflns         5769
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.108
_refine_ls_R_factor_all          0.0834
_refine_ls_R_factor_gt           0.0680
_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^)+(0.0831P)^2^+1.1700P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1983
_refine_ls_wR_factor_ref         0.2099
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4441
_reflns_number_total             5769
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            Arboridinine(1).cif
_cod_data_source_block           zhangzh_0128
_cod_original_cell_volume        1563.81(15)
_cod_database_code               4128148
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.970
_shelx_estimated_absorpt_t_min   0.936
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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:
 C10(H10), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C19(H19A,H19B), C24(H24A,H24B), C25(H25A,H25B), C27(H27A,
 H27B), C29(H29A,H29B), C30(H30A,H30B), C34(H34A,H34B)
2.c Aromatic/amide H refined with riding coordinates:
 C32(H32), C37(H37), C39(H39), C40(H40), C41(H41), C42(H42), C43(H43), C44(H44)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C31(H31A,H31B,H31C), C33(H33A,H33B,H33C), C36(H36A,H36B,
 H36C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_shelx_res_checksum              91598
_shelx_hkl_checksum              94990
_olex2_date_sample_data_collection 2019-01-28
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.382
_oxdiff_exptl_absorpt_empirical_full_min 0.676