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_7132530
_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_formula_moiety         'C12 H10 N2 O3'
_chemical_formula_sum            'C12 H10 N2 O3'
_chemical_formula_weight         230.22
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-02-18
_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                 90.067(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   12.1802(2)
_cell_length_b                   11.8247(2)
_cell_length_c                   14.6931(3)
_cell_measurement_reflns_used    7357
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      71.3130
_cell_measurement_theta_min      3.6320
_cell_volume                     2116.20(7)
_computing_cell_refinement       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.33c (Rigaku OD, 2017)'
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.968
_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    -19.00  76.00   0.50    0.80    --   42.30 -82.00 -60.00  190
  2  \w    -46.00  64.00   0.50    0.80    --   42.30 -57.00 -30.00  220
  3  \w     87.00 113.00   0.50    0.80    --   42.30  77.00-120.00   52
  4  \w    104.00 131.00   0.50    0.80    --   42.30  77.00  30.00   54
  5  \w     44.00  90.00   0.50    1.00    --  101.60 -82.00-150.00   92
  6  \w     12.00 145.00   0.50    1.00    --  101.60 -82.00-120.00  266
  7  \w     15.00  41.00   0.50    1.00    --  101.60 -82.00 150.00   52
  8  \w     64.00 189.00   0.50    1.00    --  101.60  25.00-180.00  250
  9  \w     13.00 134.00   0.50    1.00    --  101.60 -63.00-120.00  242
 10  \w     77.00 106.00   0.50    1.00    --  101.60 -82.00-180.00   58
 11  \w     71.00 115.00   0.50    1.00    --  101.60 -82.00 150.00   88
 12  \w     95.00 191.00   0.50    1.00    --  101.60  25.00 -90.00  192
 13  \w     29.00  67.00   0.50    1.00    --  101.60  25.00 -90.00   76
 14  \w     -6.00  44.00   0.50    0.80    --   42.10 -82.00 120.00  100
 15  \w    -12.00  25.00   0.50    0.80    --   42.10 -57.00-150.00   74
 16  \w     93.00 131.00   0.50    0.80    --   42.10  77.00-150.00   76
 17  \w     47.00  74.00   0.50    0.80    --   42.10 -82.00 120.00   54
 18  \w     55.00 109.00   0.50    0.80    --   42.10  57.00  90.00  108
 19  \w    -47.00  68.00   0.50    0.80    --   42.10 -57.00 150.00  230
 20  \w    114.00 156.00   0.50    1.00    --  101.60  38.00-120.00   84
 21  \w     40.00 187.00   0.50    1.00    --  101.60 -12.00-150.00  294
 22  \w     88.00 141.00   0.50    1.00    --  101.60  77.00 -60.00  106
 23  \w     22.00  62.00   0.50    1.00    --  101.60 -77.00  90.00   80
 24  \w     13.00 132.00   0.50    1.00    --  101.60 -63.00  30.00  238
 25  \w     55.00  85.00   0.50    1.00    --  101.60  38.00-120.00   60
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0851359000
_diffrn_orient_matrix_UB_12      0.0962749000
_diffrn_orient_matrix_UB_13      0.0034927000
_diffrn_orient_matrix_UB_21      0.0934341000
_diffrn_orient_matrix_UB_22      0.0872826000
_diffrn_orient_matrix_UB_23      0.0071195000
_diffrn_orient_matrix_UB_31      0.0032495000
_diffrn_orient_matrix_UB_32      0.0091450000
_diffrn_orient_matrix_UB_33      -0.1045828000
_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  0.0535
_diffrn_reflns_av_unetI/netI     0.0464
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.968
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18367
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         71.906
_diffrn_reflns_theta_min         3.629
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.886
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79579
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.33c (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.250
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         4023
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0410
_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^)+(0.0508P)^2^+0.6069P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1063
_refine_ls_wR_factor_ref         0.1115
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3401
_reflns_number_total             4023
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05212e2.cif
_cod_data_source_block           zcc-15-2
_cod_depositor_comments
;
Adding full bibliography for 7132526--7132530.cif.

2024-06-28
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C24 H20 N4 O6'
_cod_original_formula_weight         460.44
_cod_original_formula_moiety         '2(C12 H10 N2 O3)'
_cod_original_formula_units_Z            4
_cod_original_cell_volume        2116.21(7)
_cod_database_code               7132530
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C H O N P'
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C18(H18A,H18B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C10(H10), C11(H11), C14(H14),
 C15(H15), C17(H17), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24)
;
_shelx_res_checksum              39944
_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 2.467
_oxdiff_exptl_absorpt_empirical_full_min 0.561