Highly diastereoselective synthesis of tricyclic fused-pyrans by sequential hydride shift mediated double C(sp<sup>3</sup>)-H bond functionalization.
Mori, Keiji; Umehara, Nobuaki; Akiyama, Takahiko; Chemical science 9 (2018) 7327–7331; doi:10.1039/c8sc02103a

data_1549596
_publ_section_title
;
 Highly diastereoselective synthesis of tricyclic fused-pyrans by
 sequential hydride shift mediated double C(sp<sup>3</sup>)-H bond
 functionalization.
;
_journal_issue                   37
_journal_name_full               'Chemical science'
_journal_page_first              7327
_journal_page_last               7331
_journal_paper_doi               10.1039/c8sc02103a
_journal_volume                  9
_journal_year                    2018
_chemical_formula_sum            'C26 H28 N2 O4'
_chemical_formula_weight         432.50
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_audit_update_record
;
2018-04-19 deposited with the CCDC.
2018-06-25 downloaded from the CCDC.
;
_cell_angle_alpha                70.523(4)
_cell_angle_beta                 88.065(4)
_cell_angle_gamma                83.805(5)
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_cell_length_b                   10.546(3)
_cell_length_c                   14.045(4)
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_cell_measurement_temperature    123
_cell_measurement_theta_max      27.41
_cell_measurement_theta_min      2.95
_cell_volume                     1103.0(6)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHELL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
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_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.973
_diffrn_measured_fraction_theta_max 0.935
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'
_diffrn_radiation_source         'Bruker TXS fine-focus rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0559
_diffrn_reflns_Laue_measured_fraction_full 0.973
_diffrn_reflns_Laue_measured_fraction_max 0.935
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            6113
_diffrn_reflns_point_group_measured_fraction_full 0.973
_diffrn_reflns_point_group_measured_fraction_max 0.935
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.476
_diffrn_reflns_theta_min         1.538
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.787
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colorless
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_exptl_crystal_description       block
_exptl_crystal_F_000             460
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_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
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_refine_ls_number_reflns         4726
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0906
_refine_ls_R_factor_gt           0.0538
_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^)+(0.0593P)^2^+0.3285P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1188
_refine_ls_wR_factor_ref         0.1360
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3210
_reflns_number_total             4726
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc02103a2.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
'Adding full bibliography for 1549595--1549597.cif.'
_cod_database_code               1549596
_shelx_estimated_absorpt_t_min   0.991
_shelx_estimated_absorpt_t_max   0.991
_shelxl_version_number           2014/6
_shelx_res_checksum              61328