Rhodium(III)-Catalyzed Intermolecular [3+3] Annulation of Benzoxazines with Quinone Compounds: Access to Spiro-Heterocyclic Scaffolds
Wei, Qing-Yi; Zhou, Ze; Yao, Meng-Lian; Liu, Jikai; Wu, Bin; Yang, Jin-Ming; Chemical Communications  (2023) –; doi:10.1039/D3CC03609J

data_7132076
_publ_section_title
;
 Rhodium(III)-Catalyzed Intermolecular [3+3] Annulation of Benzoxazines
 with Quinone Compounds: Access to Spiro-Heterocyclic Scaffolds
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC03609J
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C20 H14 Br N O3'
_chemical_formula_sum            'C20 H14 Br N O3'
_chemical_formula_weight         396.23
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-02-16
_audit_creation_method
; 
Olex2 1.3 
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408) 
;
_audit_update_record
;
2023-05-10 deposited with the CCDC.	2023-08-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.1673(15)
_cell_length_b                   15.976(4)
_cell_length_c                   16.479(4)
_cell_measurement_reflns_used    8979
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      70.20
_cell_measurement_theta_min      3.35
_cell_volume                     1623.7(7)
_computing_cell_refinement
'SAINT V8.40B Bruker-AXS, Madison WI for PHOTON III'
_computing_data_collection       'Bruker APEX3 Bruker-AXS, Madison WI'
_computing_data_reduction
'SAINT V8.40B Bruker-AXS, Madison WI for PHOTON III'
_computing_molecular_graphics
'Bruker SHELXTL Bruker-AXS, Madison WI and local programs'
_computing_publication_material  'Bruker SHELXTL Bruker-AXS, Madison WI'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker Photon III 28 detector'
_diffrn_detector_area_resol_mean ' 7.39 for PHOTON III'
_diffrn_detector_type            'Bruker Photon III 28'
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device       'Bruker D8 Venture'
_diffrn_measurement_device_type  'Bruker Photon III'
_diffrn_measurement_method       'Profile data from \q/2\q scans'
_diffrn_radiation_monochromator  'Metaljet Helios MX'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           Synchrotron
_diffrn_radiation_wavelength     1.34139
_diffrn_radiation_xray_symbol    'Ga K\a'
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_av_unetI/netI     0.0554
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            24321
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         70.461
_diffrn_reflns_theta_min         3.352
_diffrn_source                   'METALJET liquid metal X-ray source'
_diffrn_source_current           3.57
_diffrn_source_power             0.2497215
_diffrn_source_target            Ga
_diffrn_source_type              'Sealed X-ray tube'
_diffrn_source_voltage           69.95
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.385
_exptl_absorpt_correction_T_max  0.7534
_exptl_absorpt_correction_T_min  0.5418
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 - Bruker AXS, Madison WI for PHOTON III'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.543
_refine_diff_density_min         -0.879
_refine_diff_density_rms         0.091
_refine_ls_abs_structure_details
; 
 Flack x determined using 1714 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   -0.013(11)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         4582
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0403
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0461P)^2^+0.7207P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0978
_refine_ls_wR_factor_ref         0.0988
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_full    0.980
_reflns_Friedel_fraction_max     0.949
_reflns_number_gt                4390
_reflns_number_total             4582
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc03609j2.cif
_cod_data_source_block           221220e_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_original_cell_volume        1623.6(7)
_cod_database_code               7132076
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.796
_shelx_estimated_absorpt_t_min   0.763
_olex2_refinement_description
; 
1. Fixed Uiso 
 At 1.2 times of: 
  All C(H) groups, All C(H,H) groups, All N(H) groups 
 At 1.5 times of: 
  All O(H) groups 
2.a Secondary CH2 refined with riding coordinates: 
 C7(H7A,H7B) 
2.b Aromatic/amide H refined with riding coordinates: 
 C2(H2), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13), C17(H17), 
 C18(H18), C20(H20), N1(H1) 
2.c Idealised tetrahedral OH refined as rotating group: 
 O3(H3) 
;
_shelx_res_checksum              59265
_shelx_hkl_checksum              58080
_olex2_submission_special_instructions 'No special instructions were received'