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_1565149
_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 O5'
_chemical_formula_sum            'C26 H23 N3 O5'
_chemical_formula_weight         457.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2019-12-15
_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                 110.324(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.6642(4)
_cell_length_b                   18.5733(7)
_cell_length_c                   13.4479(6)
_cell_measurement_reflns_used    1769
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      58.1690
_cell_measurement_theta_min      4.2220
_cell_volume                     2263.57(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    '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    -47.00  31.00   0.50    8.50    --  -33.50  57.00   0.00  156
  2  \w    -32.00  64.00   0.50    8.50    --   36.47 -77.00 150.00  192
  3  \w    -14.00  18.00   0.50    8.50    --   36.47 -57.00   0.00   64
  4  \w     58.00  97.00   0.50    8.50    --   36.47 178.00 -90.00   78
  5  \w     14.00  72.00   0.50    8.50    --   36.47  37.00 -30.00  116
  6  \w     57.00 110.00   0.50    8.50    --   36.47 178.00   0.00  106
  7  \w     37.00  78.00   0.50    8.50    --   36.47  57.00-180.00   82
  8  \w    -32.00  27.00   0.50    8.50    --   36.47 -77.00-150.00  118
  9  \w     38.00  63.00   0.50    8.50    --   36.47 -77.00-150.00   50
 10  \w     40.00  78.00   0.50   35.00    --  108.00 -94.00 -90.00   76
 11  \w     82.00 176.00   0.50   35.00    --  108.00  30.00-150.00  188
 12  \w     50.00 112.00   0.50   35.00    --  108.00-111.00-150.00  124
 13  \w     48.00 129.00   0.50   35.00    --  108.00 -77.00 -90.00  162
 14  \w    101.00 130.00   0.50   35.00    --  108.00 111.00-120.00   58
 15  \w     63.00 131.00   0.50   35.00    --  108.00 -30.00 150.00  136
 16  \w    106.00 171.00   0.50   35.00    --  108.00  61.00 -60.00  130
 17  \w     79.00 144.00   0.50   35.00    --  108.00 178.00-150.00  130
;
_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      -0.0416056000
_diffrn_orient_matrix_UB_12      0.0756337000
_diffrn_orient_matrix_UB_13      0.0273016000
_diffrn_orient_matrix_UB_21      0.1399874000
_diffrn_orient_matrix_UB_22      0.0311090000
_diffrn_orient_matrix_UB_23      -0.0138731000
_diffrn_orient_matrix_UB_31      -0.0870440000
_diffrn_orient_matrix_UB_32      0.0138644000
_diffrn_orient_matrix_UB_33      -0.1182468000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0376
_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       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9067
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.073
_diffrn_reflns_theta_max         67.073
_diffrn_reflns_theta_min         4.238
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.776
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85403
_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    1.342
_exptl_crystal_description       prism
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.171
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     321
_refine_ls_number_reflns         4038
_refine_ls_number_restraints     45
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.1041
_refine_ls_R_factor_gt           0.0685
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1138P)^2^+0.3704P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1907
_refine_ls_wR_factor_ref         0.2181
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2516
_reflns_number_total             4038
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc05741c2.cif
_cod_data_source_block           zzy1062
_cod_database_code               1565149
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         C40H40O2N4
_shelx_estimated_absorpt_t_max   0.970
_shelx_estimated_absorpt_t_min   0.892
_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, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 N2A-C11A
 1.44 with sigma of 0.02
 C13A-N2A
 1.44 with sigma of 0.02
 C11A-C10
 1.39 with sigma of 0.02
 C14A-N2A
 2.5 with sigma of 0.02
 C13A-C15A
 2.5 with sigma of 0.02
 C13-C14
 1.53 with sigma of 0.02
 C14A-C13A
 1.53 with sigma of 0.02
 N2A-C12
 1.43 with sigma of 0.02
 N2-C11
 1.43 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C17) \\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C14)
\\sim Ueq, Uanis(C15) \\sim Ueq, Uanis(C16) \\sim Ueq: with sigma of 0.01 and
sigma for terminal atoms of 0.02
Uanis(C21) = Uanis(C21A)
Uanis(C20) = Uanis(C20A)
Uanis(C15) = Uanis(C15A)
Uanis(C16) = Uanis(C16A)
Uanis(C17) = Uanis(C17A)
Uanis(C18) = Uanis(C18A)
Uanis(C19) = Uanis(C19A)
Uanis(C14) = Uanis(C14A)
Uanis(C13) = Uanis(C13A)
Uanis(C11) = Uanis(C11A)
Uanis(N2) = Uanis(N2A)
4. Others
 Sof(H9B)=Sof(C20A)=Sof(H20A)=Sof(C21A)=Sof(H21A)=1-FVAR(1)
 Sof(H9A)=Sof(C20)=Sof(H20)=Sof(C21)=Sof(H21)=FVAR(1)
 Sof(H12A)=Sof(N2A)=Sof(C11A)=Sof(H11A)=Sof(C13A)=Sof(H13C)=Sof(H13D)=
 Sof(C19A)=Sof(H19A)=Sof(C18A)=Sof(H18A)=Sof(C17A)=Sof(H17A)=Sof(C16A)=
 Sof(H16A)=Sof(C15A)=Sof(C14A)=1-FVAR(2)
 Sof(H12)=Sof(N2)=Sof(C11)=Sof(H11)=Sof(C13)=Sof(H13A)=Sof(H13B)=Sof(C14)=
 Sof(C19)=Sof(H19)=Sof(C18)=Sof(H18)=Sof(C17)=Sof(H17)=Sof(C16)=Sof(H16)=
 Sof(C15)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C9(H9A), C9(H9B), C12(H12), C12(H12A)
5.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C13A(H13C,H13D)
5.c Aromatic/amide H refined with riding coordinates:
 N1(H1), C1(H1A), C2(H2), C3(H3), C4(H4A), C11(H11), C19(H19), C18(H18),
 C17(H17), C16(H16), C20(H20), C21(H21), C11A(H11A), C19A(H19A), C18A(H18A),
 C17A(H17A), C16A(H16A), C20A(H20A), C21A(H21A)
5.d Fitted hexagon refined as free rotating group:
 C14(C19,C18,C17,C16,C15), C19A(C18A,C17A,C16A,C15A,C14A)
5.e Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C26(H26A,H26B,H26C)
5.f Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_shelx_res_checksum              98219
_shelx_hkl_checksum              52170
_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 1.360
_oxdiff_exptl_absorpt_empirical_full_min 0.840