Skeletal remodeling of chalcone-based pyridinium salts to access isoindoline polycycles and their bridged derivatives
Wang, Lele; Han, Hua-Bin; Gu, Lijie; Zhang, Wenjing; Zhao, Junwei; Wang, Qi-Lin; Chemical Science  (2021) –; doi:10.1039/D1SC05741C

data_1565147
_publ_section_title
;
 Skeletal remodeling of chalcone-based pyridinium salts to access
 isoindoline polycycles and their bridged derivatives
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D1SC05741C
_journal_year                    2021
_chemical_formula_moiety         'C26 H23 N3 O4'
_chemical_formula_sum            'C26 H23 N3 O4'
_chemical_formula_weight         441.47
_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   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-12-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-03-18 deposited with the CCDC.	2021-11-08 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 115.198(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.0994(5)
_cell_length_b                   10.9354(3)
_cell_length_c                   16.3508(6)
_cell_measurement_reflns_used    2870
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.3790
_cell_measurement_theta_min      5.0380
_cell_volume                     2281.11(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 0.998
_diffrn_measured_fraction_theta_max 0.998
_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    -52.00  35.00   1.00    2.10    --  -33.50  57.00   0.00   87
  2  \w     -4.00  77.00   1.00    2.10    --   36.47 -99.00 150.00   81
  3  \w     58.00  92.00   1.00    2.10    --   36.47 178.00 -60.00   34
  4  \w     66.00  96.00   1.00    2.10    --   36.47 178.00-150.00   30
  5  \w     76.00 110.00   1.00    2.10    --   36.47 178.00  90.00   34
  6  \w     -1.00  77.00   1.00    2.10    --   36.47 -99.00 -60.00   78
  7  \w      9.00  38.00   1.00    2.10    --   36.47  77.00  90.00   29
  8  \w     63.00 104.00   1.00    2.10    --   36.47  77.00  90.00   41
  9  \w     47.00  73.00   1.00   14.50    --  108.00 -30.00-150.00   26
 10  \w     78.00 118.00   1.00   14.50    --  108.00 -45.00 150.00   40
 11  \w     46.00 103.00   1.00   14.50    --  108.00 -94.00-180.00   57
 12  \w     98.00 127.00   1.00   14.50    --  108.00 -30.00-150.00   29
 13  \w    113.00 172.00   1.00   14.50    --  108.00 111.00 150.00   59
 14  \w     96.00 173.00   1.00   14.50    --  108.00  61.00 -60.00   77
 15  \w     45.00 109.00   1.00   14.50    --  108.00 -45.00   0.00   64
 16  \w     63.00 178.00   1.00   14.50    --  108.00  15.00-120.00  115
;
_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      0.0864300000
_diffrn_orient_matrix_UB_12      -0.0927519000
_diffrn_orient_matrix_UB_13      0.0536231000
_diffrn_orient_matrix_UB_21      -0.0744726000
_diffrn_orient_matrix_UB_22      -0.0620072000
_diffrn_orient_matrix_UB_23      0.0341683000
_diffrn_orient_matrix_UB_31      -0.0395202000
_diffrn_orient_matrix_UB_32      -0.0860887000
_diffrn_orient_matrix_UB_33      -0.0824242000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0227
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            8092
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.066
_diffrn_reflns_theta_max         67.066
_diffrn_reflns_theta_min         5.029
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.717
_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            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.285
_exptl_crystal_description       prism
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.253
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.040
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4065
_refine_ls_number_restraints     30
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0445
_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^)+(0.0652P)^2^+0.2535P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1156
_refine_ls_wR_factor_ref         0.1275
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3204
_reflns_number_total             4065
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc05741c2.cif
_cod_data_source_block           wll148
_cod_original_cell_volume        2281.11(14)
_cod_database_code               1565147
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C40H40O2N4
_shelx_estimated_absorpt_t_max   0.938
_shelx_estimated_absorpt_t_min   0.894
_reflns_odcompleteness_completeness 99.72
_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. Restrained distances
 C24-N3A
 1.45 with sigma of 0.02
 O4A-N3A
 1.4 with sigma of 0.02
 N2A-C11
 1.45 with sigma of 0.02
 N2A-O2A
 1.2 with sigma of 0.02
3. Rigid bond restraints
 N3, O4
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 N2, O2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
Uanis(N2) \\sim Ueq, Uanis(O2) \\sim Ueq, Uanis(N3) \\sim Ueq, Uanis(O4) \\sim
Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(O4) = Uanis(O4A)
Uanis(N3) = Uanis(N3A)
Uanis(O2) = Uanis(O2A)
Uanis(O1) = Uanis(O1A)
Uanis(N2) = Uanis(N2A)
5. Others
 Sof(O4A)=Sof(N3A)=1-FVAR(1)
 Sof(O4)=Sof(N3)=FVAR(1)
 Sof(O2A)=Sof(O1A)=Sof(N2A)=1-FVAR(2)
 Sof(O1)=Sof(O2)=Sof(N2)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C10(H10)
6.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B)
6.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C12(H12), C15(H15), C16(H16), C17(H17),
 C18(H18), C19(H19), C20(H20), C21(H21)
6.d Idealised Me refined as rotating group:
 C25(H25A,H25B,H25C), C26(H26A,H26B,H26C)
;
_shelx_res_checksum              44121
_shelx_hkl_checksum              51936
_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 1.317
_oxdiff_exptl_absorpt_empirical_full_min 0.919