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_7132528
_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         'C10 H15 Br N2 O3 S'
_chemical_formula_sum            'C10 H15 Br N2 O3 S'
_chemical_formula_weight         323.21
_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             2023-03-31
_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                 111.647(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.8851(8)
_cell_length_b                   16.802(2)
_cell_length_c                   10.6416(9)
_cell_measurement_reflns_used    2696
_cell_measurement_temperature    200.00(10)
_cell_measurement_theta_max      28.4770
_cell_measurement_theta_min      3.0030
_cell_volume                     1310.4(3)
_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      200.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_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    -44.00  -7.00   1.00    8.80    --  -11.27  77.00   0.00   37
  2  \w      7.00  65.00   1.00    8.80    --  -11.27  77.00   0.00   58
  3  \w     11.00  47.00   1.00    8.80    --   11.90  77.00 -90.00   36
  4  \w    -77.00  -5.00   1.00    6.00    --  -11.43 -57.00-120.00   72
  5  \w    -16.00  34.00   1.00    6.00    --   11.90  77.00 150.00   50
;
_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      -0.0335188000
_diffrn_orient_matrix_UB_12      -0.0396183000
_diffrn_orient_matrix_UB_13      -0.0066344000
_diffrn_orient_matrix_UB_21      -0.0465190000
_diffrn_orient_matrix_UB_22      0.0089024000
_diffrn_orient_matrix_UB_23      0.0439878000
_diffrn_orient_matrix_UB_31      -0.0779661000
_diffrn_orient_matrix_UB_32      0.0115884000
_diffrn_orient_matrix_UB_33      -0.0561770000
_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  0.0297
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6558
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.977
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.389
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.295
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57581
_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    1.638
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.555
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2256
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0342
_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^)+(0.0282P)^2^+1.2278P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0705
_refine_ls_wR_factor_ref         0.0762
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1784
_reflns_number_total             2256
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3cc05212e2.cif
_cod_data_source_block           zcc-34-2
_cod_depositor_comments
'Adding full bibliography for 7132526--7132530.cif.'
_cod_database_code               7132528
_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, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C9-C11
 1.54 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C11) \\sim Ueq: with sigma of 0.0005 and sigma for terminal atoms of 0.001
4. Rigid body (RIGU) restrains
 C7, C11, C9, S1
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.003
5. Others
 Sof(H7B)=Sof(C8)=Sof(H8)=Sof(H9BC)=Sof(H9BD)=1-FVAR(1)
 Sof(H7A)=Sof(H9AA)=Sof(H9AB)=Sof(C11)=Sof(H11)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C5(H5), C4(H4)
6.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C6(H6A,H6B), C9(H9BC,H9BD), C9(H9AA,H9AB)
6.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C7(H7B), C7(H7A), C8(H8), C11(H11)
6.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
6.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
_shelx_res_checksum              96692
_olex2_date_sample_data_collection 2023-03-31
_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 1.503
_oxdiff_exptl_absorpt_empirical_full_min 0.700