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_4128146
_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         'C18 H19 Cl N2 O'
_chemical_formula_sum            'C18 H19 Cl N2 O'
_chemical_formula_weight         314.80
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2017-05-17
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 99.527(7)
_cell_angle_gamma                90.00
_cell_formula_units_Z            12
_cell_length_a                   33.295(3)
_cell_length_b                   11.0183(7)
_cell_length_c                   12.8497(8)
_cell_measurement_reflns_used    1858
_cell_measurement_temperature    294.1(7)
_cell_measurement_theta_max      21.5340
_cell_measurement_theta_min      3.6080
_cell_volume                     4649.0(6)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_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_temperature      294.1(7)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -61.00   -7.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3492  -57.0000 -150.0000 54

  2 omega -101.00  -57.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.3492  178.0000   60.0000 44

  3 omega  -33.00    6.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305  -57.0000  -60.0000 39

  4 omega   22.00   98.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305   19.0000  120.0000 76

  5 omega  -44.00    7.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.6305   19.0000  120.0000 51
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0200523000
_diffrn_orient_matrix_UB_12      0.0193243000
_diffrn_orient_matrix_UB_13      0.0035125000
_diffrn_orient_matrix_UB_21      0.0080086000
_diffrn_orient_matrix_UB_22      0.0476313000
_diffrn_orient_matrix_UB_23      0.0343986000
_diffrn_orient_matrix_UB_31      0.0001331000
_diffrn_orient_matrix_UB_32      0.0387941000
_diffrn_orient_matrix_UB_33      -0.0440084000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_av_unetI/netI     0.1337
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_h_min       -40
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            19254
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.29
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86054
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1992
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.443
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     610
_refine_ls_number_reflns         9142
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.1704
_refine_ls_R_factor_gt           0.0792
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0668P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1619
_refine_ls_wR_factor_ref         0.2178
_reflns_number_gt                4105
_reflns_number_total             9142
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            22.cif
_cod_data_source_block           zhangzh_0517_3
_cod_original_cell_volume        4648.9(6)
_cod_database_code               4128146
_chemical_oxdiff_formula         'C H O N'
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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
2. Uiso/Uaniso restraints and constraints
Uanis(C54) \\sim Ueq, Uanis(C54') \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3. Others
 Fixed Sof: H53(0.75) H53A(0.25) C54(0.7) H54A(0.7) H54B(0.7) C54'(0.3)
 H54C(0.3) H54D(0.3)
4.a Ternary CH refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C29(H29), C31(H31), C32(H32), C47(H47),
 C48(H48), C53(H53), C53(H53A)
4.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C15(H15A,H15B), C18(H18A,H18B), C28(H28A,H28B), C33(H33A,
 H33B), C36(H36A,H36B), C49(H49A,H49B), C50(H50A,H50B), C54(H54A,H54B),
 C54'(H54C,H54D)
4.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C20(H20), C21(H21), C22(H22), C23(H23),
 C38(H38), C39(H39), C40(H40), C41(H41)
4.d Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C34(H34A,H34B,H34C), C35(H35A,H35B,
 H35C), C51(H51A,H51B,H51C), C52(H52A,H52B,H52C)
;
_olex2_date_sample_data_collection 2017-05-17
_olex2_submission_special_instructions 'No special instructions were received'