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_7132077
_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_formula_moiety         'C23 H16 Br N O3'
_chemical_formula_sum            'C23 H16 Br N O3'
_chemical_formula_weight         434.28
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2023-07-22
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-07-24 deposited with the CCDC.	2023-08-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.0778(14)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   14.11122(19)
_cell_length_b                   11.90270(16)
_cell_length_c                   26.9246(4)
_cell_measurement_reflns_used    19341
_cell_measurement_temperature    99.97(14)
_cell_measurement_theta_max      73.8230
_cell_measurement_theta_min      3.2340
_cell_volume                     4366.61(11)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL n/a (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.97(14)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -31.00  29.00   0.50    0.50    --    0.00 -82.00 120.00  120
  2  \w    -79.00 -30.00   0.50    0.50    --    0.00 -57.00-120.00   98
  3  \w      6.00 114.00   0.50    0.50    --   95.80 -45.00  90.00  216
  4  \w     87.00 127.00   0.50    0.50    --   95.80 -82.00-120.00   80
  5  \w     24.00 122.00   0.50    0.50    --   95.80 -82.00-180.00  196
  6  \w    104.00 129.00   0.50    0.50    --   95.80  82.00 120.00   50
  7  \w     20.00 100.00   0.50    0.50    --   95.80 -45.00   0.00  160
  8  \w    -44.00   8.00   0.50    0.50    --    0.00 -77.00-120.00  104
  9  \w     87.00 114.00   0.50    0.50    --   95.80 -82.00-150.00   54
 10  \w    110.00 136.00   0.50    0.50    --   95.80  30.00 -90.00   52
 11  \w     20.00  58.00   0.50    0.50    --   95.80 -82.00-150.00   76
 12  \w    -88.00 -61.00   0.50    0.50    --    0.00 -38.00 -60.00   54
 13  \w      5.00  31.00   0.50    0.50    --    0.00 -82.00  90.00   52
 14  \w    -24.00   2.00   0.50    0.50    --    0.00 -82.00-150.00   52
 15  \w    -42.00 -16.00   0.50    0.50    --    0.00 -38.00 -60.00   52
 16  \w    -31.00  -5.00   0.50    0.50    --    0.00 -82.00-180.00   52
 17  \w    -28.00  -3.00   0.50    0.50    --    0.00 -82.00  90.00   50
 18  \w    125.00 179.00   0.50    0.50    --   95.80  45.00-180.00  108
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0060943000
_diffrn_orient_matrix_UB_12      0.0306367000
_diffrn_orient_matrix_UB_13      -0.0563262000
_diffrn_orient_matrix_UB_21      -0.1128600000
_diffrn_orient_matrix_UB_22      -0.0069403000
_diffrn_orient_matrix_UB_23      -0.0129454000
_diffrn_orient_matrix_UB_31      -0.0047047000
_diffrn_orient_matrix_UB_32      0.1254986000
_diffrn_orient_matrix_UB_33      0.0130548000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            22661
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        66.601
_diffrn_reflns_theta_max         66.601
_diffrn_reflns_theta_min         3.244
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    2.741
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70774
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_description       block
_exptl_crystal_F_000             1760
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.938
_refine_diff_density_min         -0.825
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     509
_refine_ls_number_reflns         7498
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0420
_refine_ls_R_factor_gt           0.0364
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0375P)^2^+4.4237P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0922
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6477
_reflns_number_total             7498
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc03609j2.cif
_cod_data_source_block           124311
_cod_original_cell_volume        4366.61(10)
_cod_database_code               7132077
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N Br'
_shelx_estimated_absorpt_t_max   0.811
_shelx_estimated_absorpt_t_min   0.700
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Riding coordinates:
 N2(H2A)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C23(H23A,H23B), C30(H30A,H30B), C46(H46A,H46B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C10(H10), C11(H11), C13(H13), C17(H17),
 C18(H18), C21(H21), C22(H22), C25(H25), C26(H26), C27(H27), C28(H28), C33(H33),
  C34(H34), C36(H36), C40(H40), C41(H41), C44(H44), C45(H45)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              25805
_shelx_hkl_checksum              30596
_shelx_fab_checksum              59579
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.936
_oxdiff_exptl_absorpt_empirical_full_min 0.643