Catalytic Enantioselective Total Synthesis of Hypocrolide A.
Qiao, Chuang; Zhang, Wen; Han, Jing-Chun; Li, Chuang-Chuang; Organic letters 18 (2016) 4932–4935; doi:10.1021/acs.orglett.6b02414

data_1555763
_publ_section_title
;
 Catalytic Enantioselective Total Synthesis of Hypocrolide A.
;
_journal_issue                   19
_journal_name_full               'Organic letters'
_journal_page_first              4932
_journal_page_last               4935
_journal_paper_doi               10.1021/acs.orglett.6b02414
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C25 H26 O6'
_chemical_formula_weight         422.46
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.6433(2)
_cell_length_b                   8.77370(10)
_cell_length_c                   31.105(2)
_cell_measurement_reflns_used    45247
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      69.20
_cell_measurement_theta_min      6.60
_cell_volume                     4269.1(3)
_computing_cell_refinement       'CrystalClear-SM Auto 2.0 r4'
_computing_data_collection       'CrystalClear-SM 2.0 r4 (Rigaku, 2009)'
_computing_data_reduction        'CrystalClear-SM Auto 2.0 r4'
_computing_molecular_graphics    'CrystalStructure 4.0'
_computing_publication_material  'CrystalStructure 4.0 (Rigaku, 2009)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Rigaku Saturn944+ CCD'
_diffrn_measurement_method       \w
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0605
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            55870
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.687
_diffrn_reflns_theta_max         69.315
_diffrn_reflns_theta_min         6.610
_exptl_absorpt_coefficient_mu    0.766
_exptl_absorpt_correction_T_max  0.861
_exptl_absorpt_correction_T_min  0.694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_description       prism
_exptl_crystal_F_000             1792
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 2675 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.14(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     559
_refine_ls_number_reflns         7712
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0449
_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^)+(0.0816P)^2^+0.0662P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1202
_refine_ls_wR_factor_ref         0.1277
_reflns_Friedel_coverage         0.909
_reflns_Friedel_fraction_full    0.954
_reflns_Friedel_fraction_max     0.935
_reflns_number_gt                6515
_reflns_number_total             7712
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02414_si_006.cif
_cod_data_source_block           shelx
_cod_database_code               1555763
_shelx_estimated_absorpt_t_min   0.862
_shelx_estimated_absorpt_t_max   0.862
_shelxl_version_number           2014-3
_shelx_res_checksum              16056
_shelx_hkl_checksum              24963