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_7132527
_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         'C13 H13 Br N2 O3'
_chemical_formula_sum            'C13 H13 Br N2 O3'
_chemical_formula_weight         325.16
_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             2023-04-06
_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                 111.417(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.5757(3)
_cell_length_b                   12.8565(3)
_cell_length_c                   10.0965(3)
_cell_measurement_reflns_used    3966
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.3930
_cell_measurement_theta_min      4.4810
_cell_volume                     1277.99(7)
_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    '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 0.996
_diffrn_measured_fraction_theta_max 0.966
_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    -91.00 -19.00   1.00    1.00    --  -40.92 -37.00-150.00   72
  2  \w    -91.00  -9.00   1.00    1.00    --  -40.92 -77.00 -30.00   82
  3  \w     59.00  97.00   1.00    1.00    --   40.92-125.00-180.00   38
  4  \w     32.00 102.00   1.00    1.00    --  107.58 -94.00-180.00   70
  5  \w     32.00 118.00   1.00    1.00    --  107.58 -30.00-180.00   86
  6  \w     32.00 136.00   1.00    1.00    --  107.58 -30.00 -90.00  104
  7  \w     34.00  64.00   1.00    1.00    --  107.58 -77.00 120.00   30
  8  \w     30.00 105.00   1.00    1.00    --  107.58 -94.00  90.00   75
  9  \w    106.00 135.00   1.00    1.00    --  107.58 -77.00 120.00   29
 10  \w    123.00 148.00   1.00    1.00    --  107.58 125.00  30.00   25
 11  \w   -112.00 -74.00   1.00    1.00    --  -40.92-151.00 -61.00   38
;
_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      0.0593370000
_diffrn_orient_matrix_UB_12      0.0923629000
_diffrn_orient_matrix_UB_13      0.1006372000
_diffrn_orient_matrix_UB_21      0.0915422000
_diffrn_orient_matrix_UB_22      -0.0752483000
_diffrn_orient_matrix_UB_23      0.1133883000
_diffrn_orient_matrix_UB_31      0.1122635000
_diffrn_orient_matrix_UB_32      0.0125640000
_diffrn_orient_matrix_UB_33      -0.0622182000
_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  0.0497
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4547
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.571
_diffrn_reflns_theta_min         4.491
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    4.455
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.17358
_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 colourless'
_exptl_crystal_density_diffrn    1.690
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         1.339
_refine_diff_density_min         -1.956
_refine_diff_density_rms         0.304
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     172
_refine_ls_number_reflns         2498
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.038
_refine_ls_R_factor_all          0.0706
_refine_ls_R_factor_gt           0.0681
_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^)+(0.1738P)^2^+1.2875P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2046
_refine_ls_wR_factor_ref         0.2098
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2399
_reflns_number_total             2498
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05212e2.cif
_cod_data_source_block           37-1
_cod_depositor_comments
'Adding full bibliography for 7132526--7132530.cif.'
_cod_database_code               7132527
_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:
 C9(H9), C10(H10)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C13(H13)
;
_shelx_res_checksum              65027
_olex2_date_sample_data_collection 2023-04-04
_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 15.524
_oxdiff_exptl_absorpt_empirical_full_min 0.487