Diastereoselective trifunctionalization of pyridinium salts to access structurally crowded azaheteropolycycles.
Cui, Zhaohui; Zhang, Kuan; Gu, Lijie; Bu, Zhanwei; Zhao, Junwei; Wang, Qilin; Chemical communications (Cambridge, England) 57 (2021) 9402–9405; doi:10.1039/d1cc03478b

data_7128819
_publ_section_title
;
 Diastereoselective trifunctionalization of pyridinium salts to access
 structurally crowded azaheteropolycycles.
;
_journal_issue                   74
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              9402
_journal_page_last               9405
_journal_paper_doi               10.1039/d1cc03478b
_journal_volume                  57
_journal_year                    2021
_chemical_formula_moiety         'C26 H26 Br N3 O7'
_chemical_formula_sum            'C26 H26 Br N3 O7'
_chemical_formula_weight         572.41
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-09-15
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-06-19 deposited with the CCDC.	2021-08-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.088(14)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.194(5)
_cell_length_b                   12.288(3)
_cell_length_c                   18.063(6)
_cell_measurement_reflns_used    9978
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      28.140
_cell_measurement_theta_min      2.813
_cell_volume                     2474.8(15)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      149.99
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker AXS area detector'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0294
_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       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            30412
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_min         2.233
_exptl_absorpt_coefficient_mu    1.714
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0866 before and 0.0600 after correction. The Ratio of minimum to maximum transmission is 0.8978. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_description       block
_exptl_crystal_F_000             1176
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         5059
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0263
_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^)+(0.0222P)^2^+1.3889P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0566
_refine_ls_wR_factor_ref         0.0603
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4318
_reflns_number_total             5059
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc03478b2.cif
_cod_data_source_block           m4278_0m
_cod_depositor_comments
'Adding full bibliography for 7128819--7128822.cif.'
_cod_original_cell_volume        2474.7(16)
_cod_database_code               7128819
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.821
_shelx_estimated_absorpt_t_min   0.715
_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.a Ternary CH refined with riding coordinates:
 C7(H7), C15(H15), C16(H16), C17(H17)
2.b Secondary CH2 refined with riding coordinates:
 C10(H10A,H10B), C13(H13A,H13B), C20(H20A,H20B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C19(H19), C22(H22), C23(H23), C24(H24), C25(H25),
 C26(H26)
2.d Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C14(H14A,H14B,H14C)
;
_shelx_res_checksum              653
_olex2_submission_special_instructions 'No special instructions were received'