Total Syntheses of (-)-Hibiscone C and Lysergine: A Cyclization/Fragmentation Strategy.
Lu, Yandong; Yuan, Haosen; Zhou, Shijie; Luo, Tuoping; Organic letters 19 (2017) 620–623; doi:10.1021/acs.orglett.6b03778

data_1545110
_publ_section_title
;
 Total Syntheses of (-)-Hibiscone C and Lysergine: A
 Cyclization/Fragmentation Strategy.
;
_journal_issue                   3
_journal_name_full               'Organic letters'
_journal_page_first              620
_journal_page_last               623
_journal_paper_doi               10.1021/acs.orglett.6b03778
_journal_volume                  19
_journal_year                    2017
_chemical_formula_moiety         'C27 H29 N2 O4 S'
_chemical_formula_sum            'C27 H29 N2 O4 S'
_chemical_formula_weight         477.58
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2015-04-22
_audit_creation_method
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Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
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_cell_angle_alpha                106.645(6)
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_cell_angle_gamma                109.141(6)
_cell_formula_units_Z            2
_cell_length_a                   9.7966(6)
_cell_length_b                   10.1428(7)
_cell_length_c                   13.7518(10)
_cell_measurement_reflns_used    2109
_cell_measurement_temperature    180.01(10)
_cell_measurement_theta_max      26.0490
_cell_measurement_theta_min      3.9230
_cell_volume                     1184.44(17)
_computing_cell_refinement
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_data_collection
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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_computing_data_reduction
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CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
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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, 2008)'
_computing_structure_solution
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Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_temperature      180.01(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
  1 omega  -58.00   37.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       10.5454  -57.0000  -60.0000 95

  2 omega  -20.00   53.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       10.5454  -99.0000 -150.0000 73

  3 omega  -16.00   81.00   1.0000    7.0000
omega____ theta____ kappa____ phi______ frames
    -       10.5454   57.0000   90.0000 97
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0526827000
_diffrn_orient_matrix_UB_12      0.0444505000
_diffrn_orient_matrix_UB_13      -0.0194060000
_diffrn_orient_matrix_UB_21      -0.0165800000
_diffrn_orient_matrix_UB_22      -0.0642176000
_diffrn_orient_matrix_UB_23      -0.0452969000
_diffrn_orient_matrix_UB_31      -0.0579155000
_diffrn_orient_matrix_UB_32      0.0151099000
_diffrn_orient_matrix_UB_33      -0.0270505000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0804
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7485
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.016
_diffrn_reflns_theta_min         3.082
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.174
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71383
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour
;
;
_exptl_crystal_density_diffrn    1.339
_exptl_crystal_description
;
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_exptl_crystal_F_000             506
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.660
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         4616
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.1056
_refine_ls_R_factor_gt           0.0686
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1094P)^2^+0.2646P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1773
_refine_ls_wR_factor_ref         0.2132
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3112
_reflns_number_total             4616
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b03778_si_003.cif
_cod_data_source_block           exp_5139
_cod_depositor_comments          'Adding full bibliography for 1545110.cif.'
_cod_original_cell_volume        1184.44(15)
_cod_database_code               1545110
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C1 H1 O1 N1 S1'
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.966
_reflns_odcompleteness_completeness 99.23
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_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:
 C1(H1), C11(H11), C13(H13)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C14(H14A,H14B), C15(H15A,H15B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C8(H8), C12(H12), C17(H17), C19(H19), C20(H20)
2.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C25(H25A,H25B,H25C), C26(H26A,H26B,H26C), C27(H27A,H27B,
 H27C)
;
_olex2_submission_special_instructions 'No special instructions were received'