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_1565153
_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 H26 N4 O3'
_chemical_formula_sum            'C26 H26 N4 O3'
_chemical_formula_weight         442.51
_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_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
;
2021-05-28 deposited with the CCDC.	2021-11-08 downloaded from the CCDC.
;
_cell_angle_alpha                106.178(4)
_cell_angle_beta                 93.800(3)
_cell_angle_gamma                114.614(3)
_cell_formula_units_Z            2
_cell_length_a                   9.5216(3)
_cell_length_b                   10.7823(4)
_cell_length_c                   12.6332(5)
_cell_measurement_reflns_used    2433
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      67.7780
_cell_measurement_theta_min      4.7750
_cell_volume                     1107.48(8)
_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    -52.00  35.00   0.50    1.50    --  -33.50  57.00 -60.00  174
  2  \w   -108.00 -32.00   0.50    1.50    --  -33.50 178.00 120.00  152
  3  \w   -102.00 -15.00   0.50    1.50    --  -33.50 -57.00 150.00  174
  4  \w    -34.00  59.00   0.50    1.50    --   36.47 -37.00-120.00  186
  5  \w     57.00 110.00   0.50    1.50    --   36.47 178.00-180.00  106
  6  \w     57.00 110.00   0.50    1.50    --   36.47 178.00 150.00  106
  7  \w     14.00 107.00   0.50    1.50    --   36.47  37.00  60.00  186
  8  \w     -4.00  53.00   0.50    1.50    --   36.47 -99.00  30.00  114
  9  \w     11.00  40.00   0.50    1.50    --   36.47  77.00  60.00   58
 10  \w    -32.00  19.00   0.50    1.50    --   36.47 -77.00 120.00  102
 11  \w     40.00  65.00   0.50    1.50    --   36.47 -77.00 120.00   50
 12  \w     31.00 105.00   0.50    1.50    --   36.47  57.00 -30.00  148
 13  \w     19.00  72.00   0.50    1.50    --   36.47 -99.00 120.00  106
 14  \w      5.00  75.00   0.50    1.50    --   36.47 -99.00 -90.00  140
 15  \w     61.00 105.00   0.50    1.50    --   36.47  77.00  60.00   88
 16  \w    152.00 178.00   0.50    6.50    --  108.00 111.00 150.00   52
 17  \w     44.00  99.00   0.50    6.50    --  108.00-111.00 150.00  110
 18  \w     38.00 127.00   0.50    6.50    --  108.00 -45.00   0.00  178
 19  \w     80.00 132.00   0.50    6.50    --  108.00 -77.00  90.00  104
 20  \w     76.00 108.00   0.50    6.50    --  108.00 -94.00 -60.00   64
 21  \w     45.00 123.00   0.50    6.50    --  108.00 -45.00-180.00  156
 22  \w     97.00 149.00   0.50    6.50    --  108.00  30.00  30.00  104
 23  \w     37.00 122.00   0.50    6.50    --  108.00 -30.00  90.00  170
 24  \w     76.00 109.00   0.50    6.50    --  108.00 -94.00-180.00   66
 25  \w     68.00 109.00   0.50    6.50    --  108.00-111.00  90.00   82
 26  \w     40.00 127.00   0.50    6.50    --  108.00 -45.00 -90.00  174
 27  \w     60.00 101.00   0.50    6.50    --  108.00 -94.00 -90.00   82
 28  \w     38.00 178.00   0.50    6.50    --  108.00   0.00 150.00  280
;
_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      -0.0063998000
_diffrn_orient_matrix_UB_12      0.0251273000
_diffrn_orient_matrix_UB_13      0.1253772000
_diffrn_orient_matrix_UB_21      -0.1810276000
_diffrn_orient_matrix_UB_22      -0.0903974000
_diffrn_orient_matrix_UB_23      -0.0325428000
_diffrn_orient_matrix_UB_31      0.0174674000
_diffrn_orient_matrix_UB_32      -0.1381035000
_diffrn_orient_matrix_UB_33      -0.0088731000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7986
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.068
_diffrn_reflns_theta_max         67.068
_diffrn_reflns_theta_min         3.725
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.715
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86956
_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    1.327
_exptl_crystal_description       prism
_exptl_crystal_F_000             468
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.334
_refine_diff_density_min         -0.206
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     326
_refine_ls_number_reflns         3949
_refine_ls_number_restraints     40
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0570
_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^)+(0.1040P)^2^+0.0918P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1642
_refine_ls_wR_factor_ref         0.1847
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2883
_reflns_number_total             3949
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc05741c2.cif
_cod_data_source_block           zzy119
_cod_original_cell_volume        1107.47(8)
_cod_database_code               1565153
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C14H15N2O4
_shelx_estimated_absorpt_t_max   0.938
_shelx_estimated_absorpt_t_min   0.859
_reflns_odcompleteness_completeness 99.92
_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, All N(H) groups
2. Restrained distances
 C21A-N4
 1.45 with sigma of 0.02
 C25A-C24A
 1.52 with sigma of 0.02
 C24A-C23A
 1.52 with sigma of 0.02
 C26A-C25A
 1.52 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(N4) \\sim Ueq, Uanis(C22) \\sim Ueq, Uanis(C26) \\sim Ueq, Uanis(C25)
\\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C23) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C20) = Uanis(C20A)
Uanis(C21) = Uanis(C21A)
Uanis(N4) = Uanis(N4A)
Uanis(C22) = Uanis(C22A)
Uanis(C23) = Uanis(C23A)
Uanis(C24) = Uanis(C24A)
Uanis(C25) = Uanis(C25A)
Uanis(C26) = Uanis(C26A)
4. Others
 Sof(N4A)=Sof(C20A)=Sof(H20A)=Sof(C21A)=Sof(H21A)=Sof(C22A)=Sof(H22C)=
 Sof(H22D)=Sof(C23A)=Sof(H23C)=Sof(H23D)=Sof(C24A)=Sof(H24C)=Sof(H24D)=
 Sof(C25A)=Sof(H25C)=Sof(H25D)=Sof(C26A)=Sof(H26C)=Sof(H26D)=1-FVAR(1)
 Sof(N4)=Sof(C20)=Sof(H20)=Sof(C21)=Sof(H21)=Sof(C22)=Sof(H22A)=Sof(H22B)=
 Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(C25)=Sof(H25A)=
 Sof(H25B)=Sof(C26)=Sof(H26A)=Sof(H26B)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C9(H9)
5.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C22(H22A,H22B), C22A(H22C,H22D), C23(H23A,H23B), C23A(H23C,
 H23D), C24(H24A,H24B), C24A(H24C,H24D), C25(H25A,H25B), C25A(H25C,H25D),
 C26(H26A,H26B), C26A(H26C,H26D)
5.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C5(H5), C6(H6), C7(H7), C8(H8), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17), C20(H20), C20A(H20A), C21(H21), C21A(H21A)
;
_shelx_res_checksum              36264
_shelx_hkl_checksum              63701
_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 1.244
_oxdiff_exptl_absorpt_empirical_full_min 0.883