Enantioselective and collective total synthesis of pentacyclic 19-<i>nor</i>-clerodanes.
Zhang, Zhi-Mao; Zhang, Junliang; Cai, Quan; Chemical science 14 (2023) 12598–12605; doi:10.1039/d3sc04335e

data_1570171
_publ_section_title
;
 Enantioselective and collective total synthesis of pentacyclic
 19-<i>nor</i>-clerodanes.
;
_journal_issue                   44
_journal_name_full               'Chemical science'
_journal_page_first              12598
_journal_page_last               12605
_journal_paper_doi               10.1039/d3sc04335e
_journal_volume                  14
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_sum            'C19 H19 Br O5'
_chemical_formula_weight         407.25
_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
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2023-06-26 deposited with the CCDC.	2023-10-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.872(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.7480(7)
_cell_length_b                   13.0022(13)
_cell_length_c                   10.0405(11)
_cell_measurement_reflns_used    8652
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      54.104
_cell_measurement_theta_min      5.149
_cell_volume                     874.61(16)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      213(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0553
_diffrn_reflns_av_unetI/netI     0.0511
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            15392
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.575
_exptl_absorpt_coefficient_mu    2.377
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4722
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.505
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
; 
 Flack x determined using 1359 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.076(6)
_refine_ls_extinction_coef       0.015(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     228
_refine_ls_number_reflns         3412
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0314
_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^)+(0.0420P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0816
_reflns_Friedel_coverage         0.899
_reflns_Friedel_fraction_full    0.989
_reflns_Friedel_fraction_max     0.987
_reflns_number_gt                3114
_reflns_number_total             3412
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc04335e2.cif
_cod_data_source_block           mo_d8v23026_0m
_cod_depositor_comments
'Adding full bibliography for 1570171--1570173.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1570171
_shelx_estimated_absorpt_t_min   0.648
_shelx_estimated_absorpt_t_max   0.797
_shelxl_version_number           2013-4
_shelx_res_checksum              73904