Total Synthesis and Structure Revision of (-)-Avicennone C.
Kleiner, Yolanda; Hammann, Peter; Becker, Jonathan; Bauer, Armin; Pöverlein, Christoph; Schuler, Sören M M; The Journal of organic chemistry  (2020) –; doi:10.1021/acs.joc.0c01792

data_4038861
_publ_section_title
;
 Total Synthesis and Structure Revision of (-)-Avicennone C.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.0c01792
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_sum            'C26 H41 Br O4 Si'
_chemical_formula_weight         525.59
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 114.516(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.756(3)
_cell_length_b                   43.788(14)
_cell_length_c                   9.040(3)
_cell_measurement_reflns_used    9975
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.99
_cell_measurement_theta_min      2.48
_cell_volume                     2793.4(17)
_computing_cell_refinement       'SAINT 8.40A (Bruker-AXS, 2017)'
_computing_data_collection       'APEX3 v2019.1-0 (Bruker-AXS, 2017)'
_computing_data_reduction        'SAINT 8.40A (Bruker-AXS, 2017)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT-2015 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.4167
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker PHOTON100'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0843
_diffrn_reflns_av_unetI/netI     0.0684
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       54
_diffrn_reflns_limit_k_min       -54
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            69631
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_min         1.860
_diffrn_source
'I\mS micro-focus sealed tube, multilayer optics'
_exptl_absorpt_coefficient_mu    1.541
_exptl_absorpt_correction_T_max  0.7343
_exptl_absorpt_correction_T_min  0.6321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2016/2(Sheldrick, 2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.250
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1112
_exptl_crystal_size_max          0.109
_exptl_crystal_size_mid          0.073
_exptl_crystal_size_min          0.052
_refine_diff_density_max         0.674
_refine_diff_density_min         -0.662
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details
; 
 Classical Flack x used. 
;
_refine_ls_abs_structure_Flack   0.042(11)
_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     669
_refine_ls_number_reflns         11024
_refine_ls_number_restraints     1633
_refine_ls_restrained_S_all      0.995
_refine_ls_R_factor_all          0.0811
_refine_ls_R_factor_gt           0.0527
_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^)+6.2478P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1105
_reflns_Friedel_coverage         0.971
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                8558
_reflns_number_total             11024
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01792_si_003.cif
_cod_data_source_block           D20042
_cod_original_cell_volume        2793.4(15)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4038861
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_min   0.850
_shelx_estimated_absorpt_t_max   0.924
_shelx_res_checksum              11012
_shelx_hkl_checksum              9585