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_7128822
_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         'C30 H29 N3 O7'
_chemical_formula_sum            'C30 H29 N3 O7'
_chemical_formula_weight         543.56
_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     dual
_audit_creation_date             2021-05-25
_audit_creation_method
;
Olex2 1.3-alpha
(compiled 2020.09.11 svn.r3730fd0d for OlexSys, GUI svn.r6159)
;
_audit_update_record
;
2021-07-21 deposited with the CCDC.	2021-08-16 downloaded from the CCDC.
;
_cell_angle_alpha                109.475(4)
_cell_angle_beta                 94.551(4)
_cell_angle_gamma                90.087(4)
_cell_formula_units_Z            2
_cell_length_a                   8.9802(5)
_cell_length_b                   12.3650(6)
_cell_length_c                   12.6363(6)
_cell_measurement_reflns_used    4086
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      28.9390
_cell_measurement_theta_min      2.8060
_cell_volume                     1318.10(12)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_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     37.00  63.00   1.00    2.00    --  -11.27  77.00  90.00   26
  2  \w     -1.00  88.00   1.00    2.00    --   11.90  77.00 -60.00   89
  3  \w    -17.00  87.00   1.00    2.00    --   11.90  77.00  90.00  104
  4  \w    -44.00  62.00   1.00    2.00    --  -11.27  77.00-180.00  106
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0022973000
_diffrn_orient_matrix_UB_12      0.0583233000
_diffrn_orient_matrix_UB_13      0.0346413000
_diffrn_orient_matrix_UB_21      -0.0046225000
_diffrn_orient_matrix_UB_22      -0.0172483000
_diffrn_orient_matrix_UB_23      0.0478709000
_diffrn_orient_matrix_UB_31      0.0791014000
_diffrn_orient_matrix_UB_32      0.0025015000
_diffrn_orient_matrix_UB_33      0.0088756000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9912
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.998
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36377
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
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    1.370
_exptl_crystal_description       block
_exptl_crystal_F_000             572
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.0123(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     380
_refine_ls_number_reflns         4641
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0414
_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^)+(0.0439P)^2^+0.1911P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0938
_refine_ls_wR_factor_ref         0.1039
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3680
_reflns_number_total             4641
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1cc03478b2.cif
_cod_data_source_block           glj-57
_cod_depositor_comments
'Adding full bibliography for 7128819--7128822.cif.'
_cod_database_code               7128822
_shelx_shelxl_version_number     2018/3
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Sof(H29C)=Sof(H29D)=Sof(C30)=Sof(H30A)=Sof(H30B)=Sof(H30C)=1-FVAR(1)
 Sof(H29A)=Sof(H29B)=Sof(C30B)=Sof(H30D)=Sof(H30E)=Sof(H30F)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C10(H10), C22(H22)
3.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C20(H20A,H20B), C29(H29C,H29D), C29(H29A,H29B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C4(H4), C5(H5), C6(H6), C8(H8), C13(H13), C14(H14), C16(H16),
  C24(H24), C25(H25), C26(H26), C27(H27)
3.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C30(H30A,H30B,H30C), C30B(H30D,H30E,H30F)
3.e Idealised tetrahedral OH refined as rotating group:
 O7(H7)
;
_shelx_res_checksum              27368
_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 2.613
_oxdiff_exptl_absorpt_empirical_full_min 0.458