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_4128150
_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_absolute_configuration ad
_chemical_formula_moiety         'C25 H26 N2 O3'
_chemical_formula_sum            'C25 H26 N2 O3'
_chemical_formula_weight         376.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2019-01-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 95.1628(16)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   10.91514(18)
_cell_length_b                   12.1031(2)
_cell_length_c                   32.0994(6)
_cell_measurement_reflns_used    14767
_cell_measurement_temperature    173.00(10)
_cell_measurement_theta_max      69.9500
_cell_measurement_theta_min      4.1360
_cell_volume                     4223.35(13)
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      173.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0733
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_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     81.00 114.00   1.00    2.00    --  108.00-111.00 120.00   33
  2  \w    119.00 150.00   1.00    2.00    --  108.00-175.00  51.00   31
  3  \w     59.00 110.00   1.00    2.00    --  108.00-111.00   0.00   51
  4  \w     53.00  90.00   1.00    2.00    --  108.00-175.00  51.00   37
  5  \w     43.00 109.00   1.00    2.00    --   54.00-125.00 120.00   66
  6  \w     58.00 130.00   1.00    2.00    --  108.00 -63.00 150.00   72
  7  \w     77.00 172.00   1.00    2.00    --  108.00  25.00   0.00   95
  8  \w     86.00 173.00   1.00    2.00    --  108.00  63.00  60.00   87
  9  \w     75.00 110.00   1.00    2.00    --   54.00  57.00  30.00   35
 10  \w     39.00 103.00   1.00    2.00    --  108.00 -25.00  60.00   64
 11  \w     44.00 135.00   1.00    2.00    --  108.00 -91.00 150.00   91
 12  \w     45.00 134.00   1.00    2.00    --  108.00 -38.00 120.00   89
 13  \w     38.00  67.00   1.00    2.00    --  108.00-111.00 120.00   29
 14  \w     23.00  71.00   1.00    2.00    --   54.00-125.00  30.00   48
 15  \w     38.00 130.00   1.00    2.00    --  108.00 -50.00 -60.00   92
 16  \w     40.00 137.00   1.00    2.00    --  108.00 -77.00   0.00   97
 17  \w     39.00  75.00   1.00    2.00    --  108.00-111.00 -30.00   36
 18  \w     18.00  51.00   1.00    2.00    --   54.00-114.00-170.00   33
 19  \w     -5.00  74.00   1.00    2.00    --   54.00 -57.00-180.00   79
 20  \w     23.00  52.00   1.00    1.00    --    0.00  57.00 -60.00   29
 21  \w     22.00  49.00   1.00    1.00    --    0.00  57.00 -90.00   27
 22  \w     34.00 112.00   1.00    2.00    --   54.00  57.00   0.00   78
 23  \w     33.00  68.00   1.00    1.00    --    0.00  57.00 120.00   35
 24  \w    -21.00  31.00   1.00    1.00    --    0.00  57.00 120.00   52
 25  \w     35.00 116.00   1.00    2.00    --  108.00 -12.00   0.00   81
 26  \w    153.00 178.00   1.00    2.00    --  108.00 111.00-180.00   25
 27  \w    -14.00  11.00   1.00    1.00    --    0.00 -86.00  80.00   25
 28  \w    -19.00 125.00   1.00    2.00    --   54.00   0.00 -90.00  144
 29  \w    -46.00 -16.00   1.00    1.00    --    0.00 114.00 -79.00   30
;
_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      0.0571041000
_diffrn_orient_matrix_UB_12      -0.0713804000
_diffrn_orient_matrix_UB_13      -0.0329983000
_diffrn_orient_matrix_UB_21      -0.0120370000
_diffrn_orient_matrix_UB_22      -0.1030496000
_diffrn_orient_matrix_UB_23      0.0274899000
_diffrn_orient_matrix_UB_31      -0.1291354000
_diffrn_orient_matrix_UB_32      -0.0219402000
_diffrn_orient_matrix_UB_33      -0.0218693000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            30875
_diffrn_reflns_theta_full        69.94
_diffrn_reflns_theta_max         69.94
_diffrn_reflns_theta_min         3.91
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.664
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73902
_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    1.184
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1505
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.447
_refine_diff_density_min         -0.256
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.02(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1093
_refine_ls_number_reflns         15609
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0378
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0618P)^2^+0.3647P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0993
_refine_ls_wR_factor_ref         0.1013
_reflns_number_gt                15039
_reflns_number_total             15609
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            37.cif
_cod_data_source_block           zhangzh_0118
_cod_original_cell_volume        4223.37(12)
_cod_database_code               4128150
_reflns_odcompleteness_completeness 99.92
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12), C37(H37), C62(H62), C87(H87)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13a,H13b), C14(H14a,H14b), C19(H19a,H19b), C38(H38a,H38b), C39(H39a,
 H39b), C44(H44a,H44b), C63(H63a,H63b), C64(H64a,H64b), C69(H69a,H69b),
 C88(H88a,H88b), C89(H89a,H89b), C94(H94a,H94b)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5a), C21(H21), C22(H22), C23(H23),
 C24(H24), C25(H25), N3(H3a), C27(H27), C28(H28), C29(H29), C30(H30), C46(H46),
 C47(H47), C48(H48), C49(H49), C50(H50), N5(H5), C52(H52), C53(H53), C54(H54),
 C55(H55), C71(H71), C72(H72), C73(H73), C74(H74), C75(H75), N7(H7), C77(H77),
 C78(H78), C79(H79), C80(H80), C96(H96), C97(H97), C98(H98), C99(H99),
 C100(H100)
2.d Idealised Me refined as rotating group:
 C15(H15a,H15b,H15c), C17(H17a,H17b,H17c), C18(H18a,H18b,H18c), C41(H41a,H41b,
 H41c), C42(H42a,H42b,H42c), C43(H43a,H43b,H43c), C65(H65a,H65b,H65c), C67(H67a,
 H67b,H67c), C68(H68a,H68b,H68c), C90(H90a,H90b,H90c), C92(H92a,H92b,H92c),
 C93(H93a,H93b,H93c)
;
_olex2_date_sample_data_collection 2019-01-18
_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 1.472
_oxdiff_exptl_absorpt_empirical_full_min 0.518