Dearomatization-Induced Cycloaddition and Aromatization-Triggered Rearrangement: Synthesis of Vertically Expanded Five-Ring Fused Benzofurans.
Han, Dandan; Chen, Jinjin; He, Qiuqin; Fan, Renhua; Organic letters 18 (2016) 4690–4693; doi:10.1021/acs.orglett.6b02329

data_1544036
_publ_section_title
;
 Dearomatization-Induced Cycloaddition and Aromatization-Triggered
 Rearrangement: Synthesis of Vertically Expanded Five-Ring Fused
 Benzofurans.
;
_journal_issue                   18
_journal_name_full               'Organic letters'
_journal_page_first              4690
_journal_page_last               4693
_journal_paper_doi               10.1021/acs.orglett.6b02329
_journal_volume                  18
_journal_year                    2016
_chemical_formula_sum            'C34 H29 N O4'
_chemical_formula_weight         515.58
_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-2013
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.6012(15)
_cell_length_b                   14.683(2)
_cell_length_c                   38.686(6)
_cell_measurement_reflns_used    6334
_cell_measurement_temperature    223(2)
_cell_measurement_theta_max      22.54
_cell_measurement_theta_min      2.53
_cell_volume                     5453.7(14)
_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      223(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_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  0.0584
_diffrn_reflns_av_unetI/netI     0.0684
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -49
_diffrn_reflns_number            38456
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_min         1.483
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.664
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_description       prism
_exptl_crystal_F_000             2176
_exptl_crystal_size_max          0.700
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
; 
 Flack x determined using 2661 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.6(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     731
_refine_ls_number_reflns         11892
_refine_ls_number_restraints     28
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_all          0.1020
_refine_ls_R_factor_gt           0.0558
_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^)+(0.0681P)^2^+0.6726P] 
 where P=(Fo^2^+2Fc^2^)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1271
_refine_ls_wR_factor_ref         0.1490
_reflns_Friedel_coverage         0.797
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.998
_reflns_number_gt                7598
_reflns_number_total             11892
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ol6b02329_si_001.cif
_cod_data_source_block           mo_50615e
_cod_depositor_comments
;
          Adding full bibliography for 1544036.cif.

2019-08-18
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_cell_volume        5453.8(15)
_cod_original_formula_sum        'C68 H58 N2 O8'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     1031.16
_cod_database_code               1544036
_shelx_estimated_absorpt_t_min   0.945
_shelx_estimated_absorpt_t_max   0.985
_shelxl_version_number           2013-2
_shelx_res_checksum              29620
_shelx_hkl_checksum              11697