Efficient synthesis of spirooxazine-pyrans via rhodium-catalyzed [3+3] cascade spiroannulation of benzoxazines with 1-diazonaphthalen-2(1H)-ones
Huang, Junwei; Yue, Xuelin; Gao, Yijie; Feng, Yadong; Cui, Xiuling; New Journal of Chemistry 47 (2023) 14430–14435; doi:10.1039/D3NJ01894F

data_7062518
_publ_section_title
;
 Efficient synthesis of spirooxazine-pyrans via rhodium-catalyzed [3+3]
 cascade spiroannulation of benzoxazines with 1-diazonaphthalen-2(1H)-ones
;
_journal_issue                   30
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              14430
_journal_page_last               14435
_journal_paper_doi               10.1039/D3NJ01894F
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety         'C24 H17 N O2'
_chemical_formula_sum            'C24 H17 N O2'
_chemical_formula_weight         351.38
_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             2022-06-22
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-07-01 deposited with the CCDC.	2023-06-26 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.955(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.2178(2)
_cell_length_b                   10.5693(4)
_cell_length_c                   18.1416(5)
_cell_measurement_reflns_used    1749
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6590
_cell_measurement_theta_min      4.8390
_cell_volume                     1760.85(9)
_computing_cell_refinement       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.2312
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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   -103.00  -5.00   1.00    1.00    --  -33.50 -77.00  60.00   98
  2  \w    -34.00  25.00   1.00    1.00    --   36.47   0.00  30.00   59
  3  \w     58.00  83.00   1.00    1.00    --   36.47 178.00 120.00   25
  4  \w    -19.00  52.00   1.00    1.00    --   36.47 -57.00-180.00   71
  5  \w     63.00 109.00   1.00    1.00    --   36.47 178.00  60.00   46
  6  \w     22.00  66.00   1.00    1.00    --   36.47 -99.00  60.00   44
  7  \w     69.00  95.00   1.00    1.00    --   36.47   0.00  30.00   26
  8  \w     56.00  82.00   1.00    4.50    --  108.00 -94.00-180.00   26
  9  \w     79.00 131.00   1.00    4.50    --  108.00 -30.00 150.00   52
 10  \w    109.00 153.00   1.00    4.50    --  108.00 111.00  30.00   44
 11  \w     38.00 118.00   1.00    4.50    --  108.00 -45.00  90.00   80
 12  \w     85.00 153.00   1.00    4.50    --  108.00  30.00-120.00   68
 13  \w     38.00 107.00   1.00    4.50    --  108.00 -94.00  30.00   69
 14  \w     41.00 106.00   1.00    4.50    --  108.00 -94.00 -60.00   65
 15  \w     39.00  83.00   1.00    4.50    --  108.00 -94.00-120.00   44
 16  \w    101.00 176.00   1.00    4.50    --  108.00 111.00-120.00   75
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0389394000
_diffrn_orient_matrix_UB_12      -0.1396005000
_diffrn_orient_matrix_UB_13      -0.0162284000
_diffrn_orient_matrix_UB_21      0.0557356000
_diffrn_orient_matrix_UB_22      -0.0355051000
_diffrn_orient_matrix_UB_23      0.0798075000
_diffrn_orient_matrix_UB_31      -0.1533569000
_diffrn_orient_matrix_UB_32      0.0224980000
_diffrn_orient_matrix_UB_33      0.0250914000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            6450
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.079
_diffrn_reflns_theta_max         67.079
_diffrn_reflns_theta_min         4.816
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.670
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91199
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_description       block
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.0022(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     249
_refine_ls_number_reflns         3137
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0640
_refine_ls_R_factor_gt           0.0479
_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^)+(0.0791P)^2^+0.1087P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1289
_refine_ls_wR_factor_ref         0.1473
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2402
_reflns_number_total             3137
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj01894f2.cif
_cod_data_source_block           202206110
_cod_depositor_comments          'Adding full bibliography for 7062518.cif.'
_cod_database_code               7062518
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C30H3O3N1
_chemical_oxdiff_usercomment     r
_shelx_estimated_absorpt_t_max   0.936
_shelx_estimated_absorpt_t_min   0.856
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C4(H4), C10(H10), C11(H11), C12(H12), C13(H13),
 C17(H17), C18(H18), C21(H21), C22(H22), C23(H23), C24(H24)
;
_shelx_res_checksum              12989
_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 1.128
_oxdiff_exptl_absorpt_empirical_full_min 0.885