Solvent-controlled halohydroxylation or C3-C2 coupling of pyridinium salts through an interrupted dearomative reduction.
Zhang, Congcong; Chen, Qinhao; Qin, Yunlong; Bu, Zhanwei; Wang, Qilin; Chemical communications (Cambridge, England) 60 (2024) 992–995; doi:10.1039/d3cc05212e

data_7132529
_publ_section_title
;
 Solvent-controlled halohydroxylation or C3-C2 coupling of pyridinium
 salts through an interrupted dearomative reduction.
;
_journal_issue                   8
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              992
_journal_page_last               995
_journal_paper_doi               10.1039/d3cc05212e
_journal_volume                  60
_journal_year                    2024
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C24 H24 N4 O4'
_chemical_formula_sum            'C24 H24 N4 O4'
_chemical_formula_weight         432.47
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2023-04-05
_audit_creation_method
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2023-10-04 deposited with the CCDC.	2023-12-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 112.031(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.7417(2)
_cell_length_b                   13.7590(2)
_cell_length_c                   9.4773(2)
_cell_measurement_reflns_used    3328
_cell_measurement_temperature    149.99(10)
_cell_measurement_theta_max      73.3830
_cell_measurement_theta_min      5.0210
_cell_volume                     1056.67(4)
_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 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.99(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 0.980
_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     53.00  80.00   1.00    1.00    --   40.92 -99.00   0.00   27
  2  \w     27.00  67.00   1.00    1.00    --  107.58 -94.00 120.00   40
  3  \w     75.00 101.00   1.00    1.00    --  107.58 -94.00 120.00   26
  4  \w     33.00  98.00   1.00    1.00    --  107.58 -94.00  90.00   65
  5  \w     71.00 125.00   1.00    1.00    --  107.58 -30.00 -60.00   54
  6  \w    103.00 129.00   1.00    1.00    --  107.58 -45.00-150.00   26
  7  \w     83.00 159.00   1.00    1.00    --  107.58  45.00 -30.00   76
  8  \w     79.00 175.00   1.00    1.00    --  107.58  61.00   0.00   96
  9  \w     35.00  89.00   1.00    1.00    --  107.58 -45.00-150.00   54
 10  \w    -99.00 -29.00   1.00    1.00    --  -40.92 -77.00-120.00   70
 11  \w   -113.00 -13.00   1.00    1.00    --  -40.92 -57.00 120.00  100
;
_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      0.0473043000
_diffrn_orient_matrix_UB_12      0.0127879000
_diffrn_orient_matrix_UB_13      -0.1400146000
_diffrn_orient_matrix_UB_21      -0.1764687000
_diffrn_orient_matrix_UB_22      0.0350789000
_diffrn_orient_matrix_UB_23      -0.0941810000
_diffrn_orient_matrix_UB_31      0.0528289000
_diffrn_orient_matrix_UB_32      0.1055006000
_diffrn_orient_matrix_UB_33      0.0478991000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            4080
_diffrn_reflns_point_group_measured_fraction_full 0.726
_diffrn_reflns_point_group_measured_fraction_max 0.701
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.520
_diffrn_reflns_theta_min         5.034
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.772
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68823
_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            'light yellow'
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.185
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 779 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.58(15)
_refine_ls_extinction_coef       0.0074(8)
_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   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         2982
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0320
_refine_ls_R_factor_gt           0.0315
_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^)+(0.0542P)^2^+0.0672P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0838
_reflns_Friedel_coverage         0.370
_reflns_Friedel_fraction_full    0.426
_reflns_Friedel_fraction_max     0.396
_reflns_number_gt                2926
_reflns_number_total             2982
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05212e2.cif
_cod_data_source_block           1522
_cod_depositor_comments
'Adding full bibliography for 7132526--7132530.cif.'
_cod_database_code               7132529
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C10(H10A,H10B), C11(H11A,H11B), C18(H18A,H18B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C14(H14), C17(H17), C20(H20),
 C21(H21), C22(H22), C23(H23), C24(H24), C25(H25)
;
_shelx_res_checksum              21619
_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 1.413
_oxdiff_exptl_absorpt_empirical_full_min 0.509