C(sp<sup>3</sup>)-H Bond Functionalization of Benzo[ c]oxepines via C-O bond Cleavage: Formal [3+3] Synthesis of Multisubstituted Chromans.
Wang, Miao; Tang, Bo-Cheng; Xiang, Jia-Chen; Cheng, Yan; Wang, Zi-Xuan; Ma, Jin-Tian; Wu, Yan-Dong; Wu, An-Xin; The Journal of organic chemistry 83 (2018) 3409–3416; doi:10.1021/acs.joc.8b00126

data_4033527
_publ_section_title
;
 C(sp<sup>3</sup>)-H Bond Functionalization of Benzo[ c]oxepines via C-O
 bond Cleavage: Formal [3+3] Synthesis of Multisubstituted Chromans.
;
_journal_issue                   6
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              3409
_journal_page_last               3416
_journal_paper_doi               10.1021/acs.joc.8b00126
_journal_volume                  83
_journal_year                    2018
_chemical_formula_sum            'C29 H25 Br O4 S'
_chemical_formula_weight         549.46
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 101.596(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.508(4)
_cell_length_b                   9.580(4)
_cell_length_c                   23.335(9)
_cell_measurement_reflns_used    5047
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.04
_cell_measurement_theta_min      2.31
_cell_volume                     2520.1(17)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_av_sigmaI/netI    0.0556
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14890
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.78
_exptl_absorpt_coefficient_mu    1.748
_exptl_absorpt_correction_T_max  0.7438
_exptl_absorpt_correction_T_min  0.6998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.448
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1128
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.779
_refine_diff_density_min         -0.959
_refine_diff_density_rms         0.094
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.825
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         4448
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.825
_refine_ls_R_factor_all          0.0899
_refine_ls_R_factor_gt           0.0609
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1075P)^2^+13.9261P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1625
_refine_ls_wR_factor_ref         0.1951
_reflns_number_gt                3209
_reflns_number_total             4448
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo8b00126_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 

 Adding full bibliography for 4033527--4033528.cif.
;
_cod_original_cell_volume        2520.3(17)
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4033527