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_1565150
_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         'C21 H18 N2 O4, C H4 O'
_chemical_formula_sum            'C22 H22 N2 O5'
_chemical_formula_weight         394.41
_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             2021-01-26
_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                64.2362(13)
_cell_angle_beta                 78.0893(13)
_cell_angle_gamma                87.4663(15)
_cell_formula_units_Z            2
_cell_length_a                   7.5481(2)
_cell_length_b                   11.4787(3)
_cell_length_c                   12.3488(4)
_cell_measurement_reflns_used    7405
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      68.25
_cell_measurement_theta_min      4.06
_cell_volume                     941.57(5)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_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      150.0
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0632
_diffrn_reflns_av_unetI/netI     0.0561
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11740
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.437
_diffrn_reflns_theta_min         4.064
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.820
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5493
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1259 before and 0.0793 after correction. The Ratio of minimum to maximum transmission is 0.7294. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_description       block
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.397
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     278
_refine_ls_number_reflns         3432
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0606
_refine_ls_R_factor_gt           0.0543
_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^)+(0.0955P)^2^+0.2495P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1490
_refine_ls_wR_factor_ref         0.1564
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3000
_reflns_number_total             3432
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1sc05741c2.cif
_cod_data_source_block           a_CCDC1
_cod_database_code               1565150
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.923
_shelx_estimated_absorpt_t_min   0.779
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, H2 of C2, H3 of C3, H1A of C1, H9 of C9, H4 of C4, H12
  of C12, H13 of C13, H10 of C10, H18 of C18, H17 of C17, H21 of C21, H19 of
  C19, H20 of C20
 At 1.5 times of:
  All C(H,H,H) groups, H5 of C21, All C(H,H,H,H) groups, All O(H) groups
2. Restrained distances
 O5A-C22A
 1.43 with sigma of 0.02
 H1-O1
 0.9 with sigma of 0.02
 O5-C22
 1.4 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O5) = Uanis(O5A)
Uanis(C22) = Uanis(C22A)
4. Others
 Sof(O5A)=Sof(H5A)=Sof(C22A)=Sof(H22D)=Sof(H22E)=Sof(H22F)=1-FVAR(1)
 Sof(H5)=Sof(O5)=Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(H22C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10), C13(H13)
5.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C14(H14A,H14B)
5.c Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2), C3(H3), C4(H4), C12(H12), C17(H17), C18(H18), C19(H19),
 C20(H20), C21(H21)
5.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C22A(H22D,H22E,H22F)
5.e Idealised tetrahedral OH refined as rotating group:
 O5A(H5A)
;
_shelx_res_checksum              75834
_shelx_hkl_checksum              58966
_olex2_submission_special_instructions 'No special instructions were received'