Stabilising fleeting intermediates of stilbene photocyclization with amino-borane functionalisation: the rare isolation of persistent dihydrophenanthrenes and their [1,5] H-shift isomers.
Shi, Yong-Gang; Mellerup, Soren K.; Yuan, Kang; Hu, Guo-Fei; Sauriol, Francoise; Peng, Tai; Wang, Nan; Chen, Pangkuan; Wang, Suning; Chemical science 9 (2018) 3844–3855; doi:10.1039/c8sc00560e

data_1549148
_publ_section_title
;
 Stabilising fleeting intermediates of stilbene photocyclization with
 amino-borane functionalisation: the rare isolation of persistent
 dihydrophenanthrenes and their [1,5] H-shift isomers.
;
_journal_issue                   15
_journal_name_full               'Chemical science'
_journal_page_first              3844
_journal_page_last               3855
_journal_paper_doi               10.1039/c8sc00560e
_journal_volume                  9
_journal_year                    2018
_chemical_formula_sum            'C32 H34 B N S'
_chemical_formula_weight         475.47
_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'
_symmetry_space_group_name_Hall  'P 2c -2n'
_symmetry_space_group_name_H-M   'P n a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-12-17 deposited with the CCDC.
2018-03-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   32.54(4)
_cell_length_b                   9.129(10)
_cell_length_c                   9.286(12)
_cell_measurement_reflns_used    3434
_cell_measurement_temperature    180(2)
_cell_measurement_theta_max      20.98
_cell_measurement_theta_min      2.34
_cell_volume                     2758(6)
_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-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      180(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.879
_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  0.2018
_diffrn_reflns_av_unetI/netI     0.2057
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.879
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            21468
_diffrn_reflns_point_group_measured_fraction_full 0.954
_diffrn_reflns_point_group_measured_fraction_max 0.828
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.695
_diffrn_reflns_theta_min         2.317
_exptl_absorpt_coefficient_mu    0.137
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_description       Block
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.110
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_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
; 
 Flack x determined using 790 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.03(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         5909
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.004
_refine_ls_R_factor_all          0.1957
_refine_ls_R_factor_gt           0.0801
_refine_ls_shift/su_max          0.032
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1818
_refine_ls_wR_factor_ref         0.2266
_reflns_Friedel_coverage         0.779
_reflns_Friedel_fraction_full    0.906
_reflns_Friedel_fraction_max     0.772
_reflns_number_gt                2927
_reflns_number_total             5909
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8sc00560e2.cif
_cod_data_source_block           sy6d
_cod_depositor_comments
'Adding full bibliography for 1549141--1549152.cif.'
_cod_original_cell_volume        2759(6)
_cod_database_code               1549148
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_min   0.973
_shelx_estimated_absorpt_t_max   0.985
_shelx_res_checksum              48327