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_4127460
_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 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2019-03-13
_audit_creation_method
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Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
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_cell_angle_alpha                90
_cell_angle_beta                 110.123(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.3161(12)
_cell_length_b                   13.3539(5)
_cell_length_c                   15.3167(10)
_cell_measurement_reflns_used    2991
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.6000
_cell_measurement_theta_min      3.4340
_cell_volume                     2557.4(3)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
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_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      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 0.999
_diffrn_measurement_details
;
  1 omega  -23.00   19.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106  -99.0000   90.0000 42

  2 omega  -42.00   49.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106   19.0000    0.0000 91

  3 omega  -36.00   57.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.8106   19.0000   90.0000 93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0503683000
_diffrn_orient_matrix_UB_12      0.0169177000
_diffrn_orient_matrix_UB_13      -0.0002812000
_diffrn_orient_matrix_UB_21      0.0260400000
_diffrn_orient_matrix_UB_22      -0.0318165000
_diffrn_orient_matrix_UB_23      0.0381322000
_diffrn_orient_matrix_UB_31      0.0005191000
_diffrn_orient_matrix_UB_32      -0.0390442000
_diffrn_orient_matrix_UB_33      -0.0312920000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0429
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11952
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.370
_diffrn_reflns_theta_min         3.051
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.171
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81177
_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    1.334
_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         0.260
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     329
_refine_ls_number_reflns         5243
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0903
_refine_ls_R_factor_gt           0.0571
_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^)+(0.0724P)^2^+0.2670P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1382
_refine_ls_wR_factor_ref         0.1617
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3437
_reflns_number_total             5243
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b04847_si_002.cif
_cod_data_source_block           190311_s2_gj
_cod_database_code               4127460
_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 99.76
_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:
 C17(H17), C18(H18), C21(H21), C22(H22), C24(H24), C25(H25)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C26(H26A,H26B,H26C), C27(H27A,H27B,H27C), C28(H28A,H28B,
 H28C)
;
_shelx_res_checksum              43877
_shelx_hkl_checksum              38115
_olex2_submission_special_instructions 'No special instructions were received'