Asymmetric construction of dihydrobenzofuran-2,5-dione derivatives via desymmetrization of p-quinols with azlactones
Xie, Lihua; Dong, Shunxi; Zhang, Qian; Feng, Xiaoming; Liu, Xiaohua; Chemical Communications  (2018) –; doi:10.1039/C8CC08985J

data_7122697
_publ_section_title
;
 Asymmetric construction of dihydrobenzofuran-2,5-dione derivatives via
 desymmetrization of p-quinols with azlactones
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C8CC08985J
_journal_year                    2018
_chemical_absolute_configuration syn
_chemical_formula_sum            'C76 H99 B N8 O2'
_chemical_formula_weight         1167.44
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2018-11-08 deposited with the CCDC.
2018-11-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   20.6886(6)
_cell_length_b                   21.2747(5)
_cell_length_c                   21.4491(7)
_cell_measurement_reflns_used    9926
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      53.02
_cell_measurement_theta_min      2.98
_cell_volume                     9440.7(5)
_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-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      170(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'BRUKER D8 VENTURE PHOTON II'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            39183
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        54.383
_diffrn_reflns_theta_max         54.383
_diffrn_reflns_theta_min         2.968
_exptl_absorpt_coefficient_mu    0.378
_exptl_absorpt_correction_T_max  0.7507
_exptl_absorpt_correction_T_min  0.4674
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    0.820
_exptl_crystal_description       NEEDLE
_exptl_crystal_F_000             2520
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details
;
 Flack x determined using 2661 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.45(13)
_refine_ls_extinction_coef       0.00041(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   0.954
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     756
_refine_ls_number_reflns         11357
_refine_ls_number_restraints     1902
_refine_ls_restrained_S_all      0.987
_refine_ls_R_factor_all          0.1186
_refine_ls_R_factor_gt           0.0950
_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^)+(0.0700P)^2^+15.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2222
_refine_ls_wR_factor_ref         0.2388
_reflns_Friedel_coverage         0.807
_reflns_Friedel_fraction_full    0.969
_reflns_Friedel_fraction_max     0.969
_reflns_number_gt                7944
_reflns_number_total             11357
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8cc08985j2.cif
_cod_data_source_block           cu_20180530xlhbp_0ma_a_sq
_cod_database_code               7122697
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_min   0.805
_shelx_estimated_absorpt_t_max   0.985
_shelx_res_checksum              65994
_shelx_fab_checksum              76056