Synthesis of Spiropyrans and Arylquinones via Ru(II)-Catalyzed Conditions-Controlled Coupling of 3-Aryl-2H-benzoxazinones with Benzoquinones
Zhang, Mengying; He, Yuhao; Li, Song; Geng, Yuehua; Liu, Xiangyang; Yang, Xifa; Chemical Communications  (2023) –; doi:10.1039/D3CC03395C

data_7132082
_publ_section_title
;
 Synthesis of Spiropyrans and Arylquinones via Ru(II)-Catalyzed
 Conditions-Controlled Coupling of 3-Aryl-2H-benzoxazinones with
 Benzoquinones
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D3CC03395C
_journal_year                    2023
_chemical_formula_moiety         'C24 H21 N O4'
_chemical_formula_sum            'C24 H21 N O4'
_chemical_formula_weight         387.42
_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_block_doi                 10.5517/ccdc.csd.cc2fqvkl
_audit_creation_date             2022-07-07
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-04-14 deposited with the CCDC.	2023-08-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 104.869(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.5790(3)
_cell_length_b                   13.6219(3)
_cell_length_c                   11.7844(2)
_cell_measurement_reflns_used    4265
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.8560
_cell_measurement_theta_min      3.6210
_cell_volume                     1951.64(7)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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   -105.00  -4.00   1.00    1.50    --  -33.50   0.00  30.00  101
  2  \w    -94.00 -36.00   1.00    1.50    --  -33.50 -57.00-150.00   58
  3  \w    -50.00 -24.00   1.00    1.50    --  -33.50  57.00-150.00   26
  4  \w     -1.00  25.00   1.00    1.50    --  -33.50  57.00-150.00   26
  5  \w     44.00  69.00   1.00    1.50    --   36.47 -99.00-120.00   25
  6  \w     68.00 109.00   1.00    1.50    --   36.47 178.00  30.00   41
  7  \w      3.00 106.00   1.00    1.50    --   36.47  19.00 -30.00  103
  8  \w     34.00  59.00   1.00    1.50    --   36.47 -37.00 150.00   25
  9  \w      1.00  28.00   1.00    1.50    --   36.47 -99.00-120.00   27
 10  \w    -33.00   1.00   1.00    1.50    --   36.47 -37.00 150.00   34
 11  \w     23.00  72.00   1.00    1.50    --   36.47 -99.00  30.00   49
 12  \w     -2.00  76.00   1.00    1.50    --   36.47 -99.00-180.00   78
 13  \w     58.00 103.00   1.00    1.50    --   36.47 178.00-180.00   45
 14  \w     17.00 105.00   1.00    1.50    --   36.47  77.00-180.00   88
 15  \w    147.00 175.00   1.00    7.00    --  108.00  77.00-180.00   28
 16  \w     80.00 116.00   1.00    7.00    --  108.00  77.00-180.00   36
 17  \w     72.00  98.00   1.00    7.00    --  108.00 -94.00  90.00   26
 18  \w     38.00 108.00   1.00    7.00    --  108.00 -45.00 150.00   70
 19  \w     56.00 110.00   1.00    7.00    --  108.00 -94.00-150.00   54
 20  \w    101.00 176.00   1.00    7.00    --  108.00 111.00 150.00   75
 21  \w     38.00 106.00   1.00    7.00    --  108.00 -94.00 150.00   68
 22  \w     41.00 126.00   1.00    7.00    --  108.00 -61.00-120.00   85
 23  \w    106.00 134.00   1.00    7.00    --  108.00 111.00 -60.00   28
 24  \w     93.00 127.00   1.00    7.00    --  108.00 -45.00  60.00   34
 25  \w     85.00 142.00   1.00    7.00    --  108.00  77.00  90.00   57
 26  \w     71.00 108.00   1.00    7.00    --  108.00 -94.00 -60.00   37
 27  \w     43.00 126.00   1.00    7.00    --  108.00 -30.00-150.00   83
 28  \w    115.00 175.00   1.00    7.00    --  108.00  45.00-150.00   60
 29  \w    100.00 157.00   1.00    7.00    --  108.00 111.00-120.00   57
 30  \w     65.00 138.00   1.00    7.00    --  108.00-157.00 162.00   73
 31  \w     90.00 178.00   1.00    7.00    --  108.00  45.00  30.00   88
;
_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      0.0065344000
_diffrn_orient_matrix_UB_12      0.1121169000
_diffrn_orient_matrix_UB_13      0.0175998000
_diffrn_orient_matrix_UB_21      -0.1171274000
_diffrn_orient_matrix_UB_22      0.0001882000
_diffrn_orient_matrix_UB_23      0.0177915000
_diffrn_orient_matrix_UB_31      0.0479685000
_diffrn_orient_matrix_UB_32      -0.0148538000
_diffrn_orient_matrix_UB_33      0.1329119000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0365
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13721
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.075
_diffrn_reflns_theta_max         67.075
_diffrn_reflns_theta_min         3.636
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.730
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94327
_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    1.319
_exptl_crystal_description       prism
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.267
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         3476
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0485
_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^)+(0.0742P)^2^+0.3085P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1338
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2821
_reflns_number_total             3476
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc03395c2.cif
_cod_data_source_block           202207127
_cod_database_code               7132082
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C30H3O3N1
_chemical_oxdiff_usercomment     r
_shelx_estimated_absorpt_t_max   0.931
_shelx_estimated_absorpt_t_min   0.911
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 H4-O4
 0.9 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C4(H4A), C10(H10), C11(H11), C12(H12), C13(H13),
 C18(H18), C20(H20)
3.b Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_shelx_res_checksum              94429
_shelx_hkl_checksum              70722
_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 1.078
_oxdiff_exptl_absorpt_empirical_full_min 0.933