Enantioselective Total Synthesis of (-)-Arcutinine.
Nie, Wei; Gong, Jing; Chen, Zhihao; Liu, Jiazhen; Tian, Di; Song, Hao; Liu, Xiao-Yu; Qin, Yong; Journal of the American Chemical Society 141 (2019) 9712–9718; doi:10.1021/jacs.9b04847

data_4127459
_publ_section_title
;
 Enantioselective Total Synthesis of (-)-Arcutinine.
;
_journal_issue                   24
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              9712
_journal_page_last               9718
_journal_paper_doi               10.1021/jacs.9b04847
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C28 H35 N O6 S'
_chemical_formula_sum            'C28 H35 N O6 S'
_chemical_formula_weight         513.63
_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     iterative
_audit_creation_date             2018-07-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.793(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0004(4)
_cell_length_b                   19.6229(8)
_cell_length_c                   16.3447(7)
_cell_measurement_reflns_used    4623
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.4560
_cell_measurement_theta_min      3.3370
_cell_volume                     2565.7(2)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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_temperature      293.15
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0874
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -17.00   18.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -       16.8419  -57.0000  -30.0000 35

  2 omega  -25.00   24.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000    0.0000 49

  3 omega  -25.00    8.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000  -90.0000 33

  4 omega  -23.00    4.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669  -99.0000 -180.0000 27

  5 omega  -65.00  -35.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -      -14.9669 -178.0000 -150.0000 30

  6 omega  -55.00   40.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -       16.8419  -19.0000    0.0000 95

  7 omega   -1.00   84.00   1.0000   11.5000
omega____ theta____ kappa____ phi______ frames
    -       16.8419   38.0000 -180.0000 85
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0635643000
_diffrn_orient_matrix_UB_12      0.0124801000
_diffrn_orient_matrix_UB_13      0.0258742000
_diffrn_orient_matrix_UB_21      -0.0614727000
_diffrn_orient_matrix_UB_22      -0.0093781000
_diffrn_orient_matrix_UB_23      -0.0296003000
_diffrn_orient_matrix_UB_31      -0.0066530000
_diffrn_orient_matrix_UB_32      -0.0325854000
_diffrn_orient_matrix_UB_33      0.0184113000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0440
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17929
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.373
_diffrn_reflns_theta_min         3.005
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59233
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description
;
;
_exptl_crystal_F_000             1096
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         5236
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1113
_refine_ls_R_factor_gt           0.0739
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0471P)^2^+4.1515P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1542
_refine_ls_wR_factor_ref         0.1735
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3513
_reflns_number_total             5236
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b04847_si_004.cif
_cod_data_source_block           180718_s1_nw
_cod_original_cell_volume        2565.74(19)
_cod_database_code               4127459
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         c12h12n2o3s1
_shelx_estimated_absorpt_t_max   0.959
_shelx_estimated_absorpt_t_min   0.943
_reflns_odcompleteness_completeness 99.78
_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.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C7(H7A,H7B), C10(H10A,H10B), C15(H15A,
 H15B), C16(H16A,H16B)
2.c Aromatic/amide H refined with riding coordinates:
 C18(H18), C19(H19), C23(H23), C24(H24), C26(H26), C27(H27)
2.d Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C20(H20A,H20B,H20C), C21(H21A,H21B,H21C), C28(H28A,H28B,
 H28C)
;
_shelx_res_checksum              27580
_shelx_hkl_checksum              84845
_olex2_submission_special_instructions 'No special instructions were received'