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_1565151
_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         '1(C26 H22 N2 O5)'
_chemical_formula_sum            'C26 H22 N2 O5'
_chemical_formula_weight         442.45
_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   geom
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-06-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-03-27 deposited with the CCDC.	2021-11-08 downloaded from the CCDC.
;
_cell_angle_alpha                82.000(3)
_cell_angle_beta                 89.792(3)
_cell_angle_gamma                61.583(4)
_cell_formula_units_Z            4
_cell_length_a                   11.5554(4)
_cell_length_b                   11.9041(4)
_cell_length_c                   20.6216(6)
_cell_measurement_reflns_used    6025
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      70.6170
_cell_measurement_theta_min      4.2670
_cell_volume                     2464.17(17)
_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    'olex2.solve (Bourhis et al., 2015)'
_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 -18.00   0.50    1.50    --  -33.50 -57.00-180.00  168
  2  \w    -55.00 -29.00   0.50    1.50    --  -33.50  77.00  30.00   52
  3  \w     -7.00  25.00   0.50    1.50    --  -33.50  77.00  30.00   64
  4  \w    -59.00 -33.00   0.50    1.50    --  -33.50 -57.00 -90.00   52
  5  \w    -58.00 -32.00   0.50    1.50    --  -33.50 178.00 120.00   52
  6  \w     82.00 107.00   0.50    1.50    --   36.47  37.00 -30.00   50
  7  \w      2.00  33.00   0.50    1.50    --   36.47 -99.00-120.00   62
  8  \w      9.00  98.00   0.50    1.50    --   36.47  77.00 120.00  178
  9  \w     14.00  78.00   0.50    1.50    --   36.47  37.00 -30.00  128
 10  \w     45.00  75.00   0.50    1.50    --   36.47 -99.00-120.00   60
 11  \w     15.00  41.00   0.50    1.50    --   36.47  37.00  90.00   52
 12  \w     19.00  47.00   0.50    1.50    --   36.47  57.00 150.00   56
 13  \w     49.00  75.00   0.50    1.50    --   36.47  37.00  90.00   52
 14  \w    -27.00  63.00   0.50    1.50    --   36.47 -77.00   0.00  180
 15  \w     50.00  77.00   0.50    1.50    --   36.47 -99.00 -90.00   54
 16  \w     10.00  42.00   0.50    1.50    --   36.47 -99.00 -90.00   64
 17  \w     72.00 109.00   0.50    1.50    --   36.47 178.00-120.00   74
 18  \w    -35.00  21.00   0.50    1.50    --   36.47 -19.00-150.00  112
 19  \w     75.00 101.00   0.50    1.50    --   36.47  57.00 150.00   52
 20  \w     80.00 105.00   0.50    7.50    --  108.00 -94.00 -60.00   50
 21  \w     89.00 168.00   0.50    7.50    --  108.00  61.00 150.00  158
 22  \w     89.00 115.00   0.50    7.50    --  108.00  77.00 -30.00   52
 23  \w     85.00 130.00   0.50    7.50    --  108.00 -77.00  60.00   90
 24  \w     43.00 111.00   0.50    7.50    --  108.00-111.00-120.00  136
 25  \w    133.00 175.00   0.50    7.50    --  108.00  30.00-180.00   84
 26  \w     41.00 128.00   0.50    7.50    --  108.00 -45.00   0.00  174
 27  \w     82.00 108.00   0.50    7.50    --  108.00  30.00-180.00   52
 28  \w     39.00 127.00   0.50    7.50    --  108.00 -45.00-180.00  176
 29  \w     55.00 109.00   0.50    7.50    --  108.00 -94.00  90.00  108
 30  \w    105.00 131.00   0.50    7.50    --  108.00 111.00-150.00   52
 31  \w     64.00 119.00   0.50    7.50    --  108.00 178.00  60.00  110
 32  \w     73.00 123.00   0.50    7.50    --  108.00 -45.00  90.00  100
 33  \w     38.00 112.00   0.50    7.50    --  108.00-111.00  60.00  148
 34  \w     64.00 178.00   0.50    7.50    --  108.00   0.00 120.00  228
 35  \w     63.00 137.00   0.50    7.50    --  108.00 -77.00-120.00  148
;
_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      0.0659802000
_diffrn_orient_matrix_UB_12      0.0556547000
_diffrn_orient_matrix_UB_13      0.0409196000
_diffrn_orient_matrix_UB_21      -0.1329452000
_diffrn_orient_matrix_UB_22      0.1242534000
_diffrn_orient_matrix_UB_23      -0.0015494000
_diffrn_orient_matrix_UB_31      -0.0327024000
_diffrn_orient_matrix_UB_32      -0.0604757000
_diffrn_orient_matrix_UB_33      0.0635926000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            17983
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.069
_diffrn_reflns_theta_max         67.069
_diffrn_reflns_theta_min         4.275
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.685
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.59573
_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    1.193
_exptl_crystal_description       prism
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.315
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     606
_refine_ls_number_reflns         8791
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0650
_refine_ls_R_factor_gt           0.0505
_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^)+(0.0852P)^2^+0.3079P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1427
_refine_ls_wR_factor_ref         0.1574
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6803
_reflns_number_total             8791
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc05741c2.cif
_cod_data_source_block           wll149_sq
_cod_original_cell_volume        2464.17(16)
_cod_database_code               1565151
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C14H15N2O4
_shelx_estimated_absorpt_t_max   0.941
_shelx_estimated_absorpt_t_min   0.898
_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. Uiso/Uaniso restraints and constraints
Uanis(C22) = Uanis(C22A)
Uanis(C23) = Uanis(C23A)
Uanis(C24) = Uanis(C24A)
Uanis(C25) = Uanis(C25A)
Uanis(C26) = Uanis(C26A)
Uanis(C21) = Uanis(C21A)
3. Others
 Sof(C21A)=Sof(C26A)=Sof(H26A)=Sof(C25A)=Sof(H25A)=Sof(C24A)=Sof(H24A)=
 Sof(C23A)=Sof(H23A)=Sof(C22A)=Sof(H22A)=1-FVAR(1)
 Sof(C21)=Sof(C22)=Sof(H22)=Sof(C23)=Sof(H23)=Sof(C24)=Sof(H24)=Sof(C25)=
 Sof(H25)=Sof(C26)=Sof(H26)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C8'(H8'), C9'(H9'), C10'(H10')
4.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C7'(H7'A,H7'B)
4.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C12(H12), C14(H14), C26A(H26A), C25A(H25A),
 C24A(H24A), C23A(H23A), C22A(H22A), C22(H22), C23(H23), C24(H24), C25(H25),
 C26(H26), C1'(H1'), C2'(H2'), C3'(H3'), C4'(H4'), C12'(H12'), C14'(H14'),
 C22'(H22'), C23'(H23'), C24'(H24'), C25'(H25'), C26'(H26')
4.d Fitted hexagon refined as free rotating group:
 C21A(C26A,C25A,C24A,C23A,C22A)
4.e Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C19(H19A,H19B,H19C), C17'(H17D,H17E,H17F), C19'(H19D,
 H19E,H19F)
;
_shelx_res_checksum              74223
_shelx_hkl_checksum              96526
_shelx_fab_checksum              46070
_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 2.086
_oxdiff_exptl_absorpt_empirical_full_min 0.766