Synthesis of spiropyrans <i>via</i> Ru(II)-catalyzed coupling of 3-aryl-2<i>H</i>-benzo[<i>b</i>][1,4]oxazines with benzoquinones.
Wen, Mengke; Zhang, Mengying; Gu, Fan; Geng, Yuehua; Liu, Xiangyang; Wu, Qingnan; Yang, Xifa; Organic & biomolecular chemistry 22 (2024) 998–1009; doi:10.1039/d3ob01971c

data_7159737
_publ_section_title
;
 Synthesis of spiropyrans <i>via</i> Ru(II)-catalyzed coupling of
 3-aryl-2<i>H</i>-benzo[<i>b</i>][1,4]oxazines with benzoquinones.
;
_journal_issue                   5
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              998
_journal_page_last               1009
_journal_paper_doi               10.1039/d3ob01971c
_journal_volume                  22
_journal_year                    2024
_chemical_formula_moiety         'C22 H20 N2 O4 S'
_chemical_formula_sum            'C22 H20 N2 O4 S'
_chemical_formula_weight         408.46
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_block_doi                 10.5517/ccdc.csd.cc2h8ml0
_audit_creation_date             2022-08-29
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2023-10-19 deposited with the CCDC.	2023-12-26 downloaded from the CCDC.
;
_cell_angle_alpha                87.571(6)
_cell_angle_beta                 71.911(7)
_cell_angle_gamma                80.248(5)
_cell_formula_units_Z            2
_cell_length_a                   9.6568(6)
_cell_length_b                   10.2090(6)
_cell_length_c                   13.0889(11)
_cell_measurement_reflns_used    1836
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      64.7880
_cell_measurement_theta_min      4.3790
_cell_volume                     1208.81(15)
_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   -102.00 -15.60   0.80    2.00    --  -33.50 -57.00-150.00  108
  2  \w    -56.00  36.00   0.80    2.00    --  -33.50  37.00 120.00  115
  3  \w   -104.00 -12.00   0.80    2.00    --  -33.50 -37.00 -60.00  115
  4  \w      8.00 105.60   0.80    2.00    --   36.47  77.00 120.00  122
  5  \w     -4.00  76.00   0.80    2.00    --   36.47 -99.00-180.00  100
  6  \w     59.00  87.80   0.80    2.00    --   36.47 178.00   0.00   36
  7  \w     25.00  61.00   0.80    2.00    --   36.47 -77.00-120.00   45
  8  \w      9.00  42.60   0.80    2.00    --   36.47  77.00   0.00   42
  9  \w     36.00  76.00   0.80    2.00    --   36.47 -99.00  90.00   50
 10  \w     15.00  51.00   0.80    2.00    --   36.47  37.00  30.00   45
 11  \w     21.00  48.20   0.80    2.00    --   36.47  57.00 120.00   34
 12  \w     72.00  98.40   0.80    2.00    --   36.47  37.00  30.00   33
 13  \w     77.00 109.00   0.80    2.00    --   36.47 178.00 -60.00   40
 14  \w    -28.00  18.40   0.80    2.00    --   36.47 -77.00-120.00   58
 15  \w     74.00 101.20   0.80    2.00    --   36.47 178.00  60.00   34
 16  \w     76.00 130.40   0.80   13.00    --  108.00 -77.00-180.00   68
 17  \w    116.00 176.00   0.80   13.00    --  108.00  30.00 -60.00   75
 18  \w     37.00 123.40   0.80   13.00    --  108.00 -30.00 -90.00  108
 19  \w    101.00 174.60   0.80   13.00    --  108.00  61.00-150.00   92
 20  \w     52.00 108.00   0.80   13.00    --  108.00-111.00  90.00   70
 21  \w     92.00 133.60   0.80   13.00    --  108.00 -77.00 120.00   52
 22  \w     39.00 109.40   0.80   13.00    --  108.00 -94.00 120.00   88
 23  \w     44.00 121.60   0.80   13.00    --  108.00 -45.00  90.00   97
 24  \w     86.00 110.80   0.80   13.00    --  108.00-111.00 -60.00   31
 25  \w    121.00 174.60   0.80   13.00    --  108.00  45.00  90.00   67
 26  \w     38.00 106.00   0.80   13.00    --  108.00 -94.00 -30.00   85
 27  \w     41.00  68.20   0.80   13.00    --  108.00-111.00 -60.00   34
 28  \w     83.00 107.80   0.80   13.00    --  108.00 -92.00-130.00   31
 29  \w     67.00 127.00   0.80   13.00    --  108.00 -61.00 -60.00   75
 30  \w     79.00 176.60   0.80   13.00    --  108.00  77.00-120.00  122
 31  \w    113.00 158.60   0.80   13.00    --  108.00  30.00-180.00   57
;
_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      0.0863968000
_diffrn_orient_matrix_UB_12      -0.1413688000
_diffrn_orient_matrix_UB_13      -0.0306667000
_diffrn_orient_matrix_UB_21      0.0290535000
_diffrn_orient_matrix_UB_22      -0.0119790000
_diffrn_orient_matrix_UB_23      0.1095568000
_diffrn_orient_matrix_UB_31      -0.1436671000
_diffrn_orient_matrix_UB_32      -0.0576057000
_diffrn_orient_matrix_UB_33      0.0488863000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0529
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8624
_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         3.553
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    1.410
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.92369
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.122
_exptl_crystal_description       block
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.194
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.056
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4320
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.992
_refine_ls_R_factor_all          0.0795
_refine_ls_R_factor_gt           0.0587
_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^)+(0.1085P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1734
_refine_ls_wR_factor_ref         0.1920
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2985
_reflns_number_total             4320
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ob01971c2.cif
_cod_data_source_block           202208152
_cod_depositor_comments
'Adding full bibliography for 7159736--7159738.cif.'
_cod_original_cell_volume        1208.82(16)
_cod_database_code               7159737
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C30H3O3N2S1
_chemical_oxdiff_usercomment     r
_shelx_estimated_absorpt_t_max   0.872
_shelx_estimated_absorpt_t_min   0.796
_reflns_odcompleteness_completeness 99.95
_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
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2A), C3(H3), C4(H4), C10(H10), C11(H11), C12(H12), C13(H13),
 C17(H17), C18(H18), C20(H20)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C)
;
_shelx_res_checksum              97519
_shelx_fab_checksum              47561
_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 1.248
_oxdiff_exptl_absorpt_empirical_full_min 0.863