Diastereoselective Intramolecular Heck Reaction Assisted by an Acetate Group: Synthesis of the Decahydrobenzofluorene Derivative Dasyscyphin E.
Jiménez, Fermín; Fernández, Antonio; Boulifa, Ettahir; Mansour, Ahmed Ibn; Alvarez-Manzaneda, Ramón; Chahboun, Rachid; Alvarez-Manzaneda, Enrique; The Journal of organic chemistry 82 (2017) 9550–9559; doi:10.1021/acs.joc.7b01551

data_4033072
_publ_section_title
;
 Diastereoselective Intramolecular Heck Reaction Assisted by an Acetate
 Group: Synthesis of the Decahydrobenzofluorene Derivative Dasyscyphin E.
;
_journal_issue                   18
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              9550
_journal_page_last               9559
_journal_paper_doi               10.1021/acs.joc.7b01551
_journal_volume                  82
_journal_year                    2017
_chemical_formula_sum            'C25 H35 O5.5'
_chemical_formula_weight         423.53
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 98.419(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   27.4647(17)
_cell_length_b                   9.7877(6)
_cell_length_c                   17.8406(11)
_cell_measurement_reflns_used    6827
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      42.16
_cell_measurement_theta_min      2.50
_cell_volume                     4744.2(5)
_computing_cell_refinement       'Bruker Apex II'
_computing_data_collection       'Bruker ApexII'
_computing_data_reduction        'Bruker Apex II'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'Phi and Omega Scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71069
_diffrn_reflns_av_R_equivalents  0.0241
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9274
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        18.033
_diffrn_reflns_theta_max         18.033
_diffrn_reflns_theta_min         1.154
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.895
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS (Bruker, 1999)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1832
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.268
_refine_diff_density_min         -0.109
_refine_diff_density_rms         0.027
_refine_ls_abs_structure_details
;
 Flack x determined using 1274 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.9(6)
_refine_ls_extinction_coef       0.0041(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     575
_refine_ls_number_reflns         3277
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0322
_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^)+(0.0447P)^2^+1.5884P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0721
_refine_ls_wR_factor_ref         0.0751
_reflns_Friedel_coverage         0.832
_reflns_Friedel_fraction_full    0.987
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                3046
_reflns_number_total             3277
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo7b01551_si_002.cif
_cod_data_source_block           shelx
_cod_depositor_comments
;

2020-08-12
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum        'C50 H70 O11'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     847.06
_cod_database_code               4033072
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_min   0.974
_shelx_estimated_absorpt_t_max   0.998
_shelx_res_checksum              55169
_shelx_hkl_checksum              42424