Total Synthesis of (-)-Chanoclavine I and an Oxygen-Substituted Ergoline Derivative.
Lu, Jia-Tian; Shi, Zi-Fa; Cao, Xiao-Ping; The Journal of organic chemistry 82 (2017) 7774–7782; doi:10.1021/acs.joc.7b00573

data_4032747
_publ_section_title
;
 Total Synthesis of (-)-Chanoclavine I and an Oxygen-Substituted Ergoline
 Derivative.
;
_journal_issue                   15
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              7774
_journal_page_last               7782
_journal_paper_doi               10.1021/acs.joc.7b00573
_journal_volume                  82
_journal_year                    2017
_chemical_formula_moiety         'C31 H32 N2 O6 S2'
_chemical_formula_sum            'C31 H32 N2 O6 S2'
_chemical_formula_weight         592.71
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2016-12-06
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_cell_angle_alpha                90.00
_cell_angle_beta                 111.139(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   20.918(2)
_cell_length_b                   6.0208(6)
_cell_length_c                   25.025(2)
_cell_measurement_reflns_used    1672
_cell_measurement_temperature    290.0(4)
_cell_measurement_theta_max      22.3680
_cell_measurement_theta_min      3.7260
_cell_volume                     2939.6(5)
_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      290.0(4)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.9968
_diffrn_measured_fraction_theta_max 0.8839
_diffrn_measurement_details
;
  1 omega   -6.00   20.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -19.5055  -99.0000   30.0000 26

  2 omega  -46.00   46.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867  -57.0000 -120.0000 92

  3 omega   38.00   81.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   38.0000   90.0000 43

  4 omega    5.00   96.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       22.7867   38.0000   30.0000 91
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0074743000
_diffrn_orient_matrix_UB_12      0.1129769000
_diffrn_orient_matrix_UB_13      0.0077486000
_diffrn_orient_matrix_UB_21      0.0059769000
_diffrn_orient_matrix_UB_22      -0.0270383000
_diffrn_orient_matrix_UB_23      0.0289629000
_diffrn_orient_matrix_UB_31      0.0351162000
_diffrn_orient_matrix_UB_32      -0.0192636000
_diffrn_orient_matrix_UB_33      0.0047226000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_av_unetI/netI     0.0873
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            11607
_diffrn_reflns_theta_full        26.02
_diffrn_reflns_theta_max         26.02
_diffrn_reflns_theta_min         3.36
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.87206
_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    1.339
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1248
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.247
_refine_diff_density_min         -0.283
_refine_diff_density_rms         0.049
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     375
_refine_ls_number_reflns         5795
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.1187
_refine_ls_R_factor_gt           0.0598
_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^)+(0.0383P)^2^+0.0750P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1127
_refine_ls_wR_factor_ref         0.1476
_reflns_number_gt                3205
_reflns_number_total             5795
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo7b00573_si_003.cif
_cod_data_source_block           lujt_1206
_cod_database_code               4032747
_chemical_oxdiff_formula         'C H N O'
_reflns_odcompleteness_completeness 99.68
_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:
 C4(H4), C5(H5)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C7(H7), C8(H8), C9(H9), C12(H12), C18(H18), C19(H19), C21(H21),
 C22(H22), C26(H26), C27(H27), C29(H29), C30(H30)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C16(H16A,H16B,H16C), C23(H23A,H23B,H23C), C24(H24A,H24B,
 H24C), C31(H31A,H31B,H31C)
;
_olex2_date_sample_data_collection 2016-12-06
_olex2_submission_special_instructions 'No special instructions were received'