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_1545212
_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_absolute_configuration syn
_chemical_formula_moiety         'C21 H27 Br O4'
_chemical_formula_sum            'C21 H27 Br O4'
_chemical_formula_weight         423.33
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2017-01-07
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.2720(5)
_cell_length_b                   7.7404(6)
_cell_length_c                   40.175(3)
_cell_measurement_reflns_used    1406
_cell_measurement_temperature    180.00(10)
_cell_measurement_theta_max      26.1460
_cell_measurement_theta_min      3.2600
_cell_volume                     1950.4(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_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      180.00(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details
;
  1 omega   13.00   58.00   0.7500    2.1800
omega____ theta____ kappa____ phi______ frames
    -      -11.7954    0.0000 -150.0000 60

  2 omega  -88.00  -25.75   0.7500    2.1800
omega____ theta____ kappa____ phi______ frames
    -      -11.7954    0.0000 -150.0000 83
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      0.0360010000
_diffrn_orient_matrix_UB_12      -0.0864248000
_diffrn_orient_matrix_UB_13      -0.0016469000
_diffrn_orient_matrix_UB_21      0.0763541000
_diffrn_orient_matrix_UB_22      0.0270564000
_diffrn_orient_matrix_UB_23      -0.0119455000
_diffrn_orient_matrix_UB_31      0.0752534000
_diffrn_orient_matrix_UB_32      0.0139327000
_diffrn_orient_matrix_UB_33      0.0128968000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_unetI/netI     0.0774
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_number            5027
_diffrn_reflns_point_group_measured_fraction_full 0.925
_diffrn_reflns_point_group_measured_fraction_max 0.917
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.008
_diffrn_reflns_theta_min         3.287
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    2.131
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59642
_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    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.067
_refine_ls_abs_structure_details
;
 Flack x determined using 929 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.002(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3532
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0434
_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^)+(0.0059P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0727
_refine_ls_wR_factor_ref         0.0783
_reflns_Friedel_coverage         0.566
_reflns_Friedel_fraction_full    0.830
_reflns_Friedel_fraction_max     0.810
_reflns_number_gt                2969
_reflns_number_total             3532
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b03778_si_002.cif
_cod_data_source_block           exp_6038
_cod_database_code               1545212
_shelxl_version_number           2014-3
_chemical_oxdiff_formula         'C21 H27 Br1 O4'
_shelx_estimated_absorpt_t_max   0.901
_shelx_estimated_absorpt_t_min   0.815
_reflns_odcompleteness_completeness 98.79
_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, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C8(H8), C9(H9), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C5(H5a,H5b), C6(H6a,H6b), C7(H7a,H7b), C10(H10a,H10b), C14(H14a,H14b)
2.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C20(H20), C21(H21)
2.d Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c), C13(H13a,H13b,H13c)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_olex2_submission_special_instructions 'No special instructions were received'