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_4038862
_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            'C15 H16 O3'
_chemical_formula_weight         244.28
_space_group_crystal_system      hexagonal
_space_group_IT_number           170
_space_group_name_Hall           'P 65'
_space_group_name_H-M_alt        'P 65'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            30
_cell_length_a                   24.0111(15)
_cell_length_b                   24.0111(15)
_cell_length_c                   22.650(2)
_cell_measurement_reflns_used    9754
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      77.28
_cell_measurement_theta_min      3.68
_cell_volume                     11309.0(14)
_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-2018/3 (Sheldrick, 2018)'
_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           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.1135
_diffrn_reflns_av_unetI/netI     0.0729
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            87282
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         74.491
_diffrn_reflns_theta_min         2.125
_diffrn_source
'I\mS micro-focus sealed tube, multilayer optics'
_exptl_absorpt_coefficient_mu    0.602
_exptl_absorpt_correction_T_max  0.7541
_exptl_absorpt_correction_T_min  0.3687
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2016/2(Sheldrick, 2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.076
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             3900
_exptl_crystal_size_max          0.944
_exptl_crystal_size_mid          0.088
_exptl_crystal_size_min          0.086
_refine_diff_density_max         1.001
_refine_diff_density_min         -1.114
_refine_diff_density_rms         0.059
_refine_ls_abs_structure_details
; 
 Flack x determined using 4902 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.12(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1220
_refine_ls_number_reflns         15339
_refine_ls_number_restraints     4677
_refine_ls_restrained_S_all      0.935
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0696
_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^)+(0.1250P)^2^+2.6714P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1835
_refine_ls_wR_factor_ref         0.1986
_reflns_Friedel_coverage         0.940
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.991
_reflns_number_gt                12566
_reflns_number_total             15339
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo0c01792_si_002.cif
_cod_data_source_block           D19459_sq
_cod_original_cell_volume        11308.7(18)
_cod_database_code               4038862
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.600
_shelx_estimated_absorpt_t_max   0.950
_shelx_res_checksum              28071
_shelx_hkl_checksum              70329
_shelx_fab_checksum              34543