#------------------------------------------------------------------------------
#$Date: 2023-05-05 03:11:16 +0300 (Fri, 05 May 2023) $
#$Revision: 283043 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/12/7131296.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7131296
loop_
_publ_author_name
'Qiu, Dong'
'Liu, Huiyang'
'Sun, Shuai'
'Ni, Hongyan'
'Su, Yijin'
_publ_section_title
;
 Bromide-mediated, C2-selective, and oxygenative alkylation of pyridinium
 salts using alkenes and molecular oxygen.
;
_journal_issue                   19
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2807
_journal_page_last               2810
_journal_paper_doi               10.1039/d2cc06138d
_journal_volume                  59
_journal_year                    2023
_chemical_formula_sum            'C24 H21 N O6'
_chemical_formula_weight         419.42
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2023-01-14 deposited with the CCDC.	2023-02-15 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 110.2940(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.4202(7)
_cell_length_b                   18.5520(13)
_cell_length_c                   12.6365(9)
_cell_measurement_reflns_used    4335
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.90
_cell_measurement_theta_min      2.20
_cell_volume                     2071.3(3)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART APEX II'
_computing_data_reduction        'Bruker SMART'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            10414
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.04
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.9808
_exptl_absorpt_correction_T_min  0.9714
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             880
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.176
_refine_diff_density_min         -0.178
_refine_diff_density_rms         0.032
_refine_ls_extinction_coef       0.0239(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     283
_refine_ls_number_reflns         3642
_refine_ls_number_restraints     13
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0371
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0200P)²+0.8322P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0773
_refine_ls_wR_factor_ref         0.0822
_reflns_number_gt                2992
_reflns_number_total             3642
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d2cc06138d2.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

data item '_symmetry_cell_setting' value 'Monoclinic' was changed to
'monoclinic' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7131296--7131297.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               7131296
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.20089(18) 0.21597(9) -0.05617(14) 0.0467(4) Uani 1 1 d . . .
C2 C 0.1409(2) 0.21971(10) -0.17297(15) 0.0581(5) Uani 1 1 d . . .
H2 H 0.0601 0.1902 -0.2125 0.070 Uiso 1 1 calc R . .
C3 C 0.2007(3) 0.26695(12) -0.23067(18) 0.0729(6) Uani 1 1 d . . .
H3 H 0.1593 0.2695 -0.3089 0.087 Uiso 1 1 calc R . .
C4 C 0.3199(3) 0.30985(12) -0.1738(2) 0.0794(7) Uani 1 1 d . . .
H4 H 0.3610 0.3409 -0.2133 0.095 Uiso 1 1 calc R . .
C5 C 0.3793(3) 0.30734(12) -0.0586(2) 0.0810(7) Uani 1 1 d . . .
H5 H 0.4600 0.3371 -0.0200 0.097 Uiso 1 1 calc R . .
C6 C 0.3202(2) 0.26084(10) 0.00064(17) 0.0651(5) Uani 1 1 d . . .
H6 H 0.3607 0.2597 0.0790 0.078 Uiso 1 1 calc R . .
C7 C 0.13621(18) 0.16257(9) 0.00185(14) 0.0470(4) Uani 1 1 d . . .
C8 C 0.19977(18) 0.15520(9) 0.13001(14) 0.0465(4) Uani 1 1 d . . .
C9 C 0.20935(17) 0.08059(8) 0.17796(13) 0.0423(4) Uani 1 1 d . . .
H9A H 0.1777 0.0462 0.1164 0.051 Uiso 1 1 calc R . .
H9B H 0.1395 0.0769 0.2189 0.051 Uiso 1 1 calc R . .
C10 C 0.37030(16) 0.06029(8) 0.25828(12) 0.0365(3) Uani 1 1 d . . .
C11 C 0.47728(17) 0.05949(8) 0.19003(12) 0.0366(3) Uani 1 1 d . . .
C13 C 0.5113(2) 0.09682(9) 0.02613(14) 0.0520(4) Uani 1 1 d U . .
H13 H 0.4731 0.1211 -0.0423 0.062 Uiso 1 1 calc R . .
C14 C 0.6495(2) 0.06721(9) 0.05504(14) 0.0524(4) Uani 1 1 d U . .
H14 H 0.7038 0.0701 0.0062 0.063 Uiso 1 1 calc R . .
C15 C 0.71213(18) 0.03172(9) 0.15967(14) 0.0468(4) Uani 1 1 d . . .
C16 C 0.8582(2) 0.00105(10) 0.19688(19) 0.0623(5) Uani 1 1 d . . .
H16 H 0.9143 0.0011 0.1491 0.075 Uiso 1 1 calc R . .
C17 C 0.9179(2) -0.02840(11) 0.3005(2) 0.0703(6) Uani 1 1 d . . .
H17 H 1.0156 -0.0471 0.3243 0.084 Uiso 1 1 calc R . .
C18 C 0.8337(2) -0.03105(10) 0.37250(17) 0.0612(5) Uani 1 1 d . . .
H18 H 0.8760 -0.0512 0.4440 0.073 Uiso 1 1 calc R . .
C19 C 0.69043(18) -0.00433(9) 0.33864(14) 0.0480(4) Uani 1 1 d . . .
H19 H 0.6348 -0.0075 0.3866 0.058 Uiso 1 1 calc R . .
C20 C 0.62479(17) 0.02832(8) 0.23137(13) 0.0398(4) Uani 1 1 d . . .
C21 C 0.35321(16) -0.01477(9) 0.30213(13) 0.0414(4) Uani 1 1 d . . .
C22 C 0.3125(2) -0.13751(10) 0.25136(18) 0.0733(6) Uani 1 1 d . . .
H22A H 0.3958 -0.1509 0.3175 0.110 Uiso 1 1 calc R . .
H22B H 0.3091 -0.1689 0.1901 0.110 Uiso 1 1 calc R . .
H22C H 0.2197 -0.1416 0.2663 0.110 Uiso 1 1 calc R . .
C23 C 0.43517(17) 0.11335(9) 0.35732(13) 0.0417(4) Uani 1 1 d . . .
H23A H 0.5196 0.0898 0.4140 0.050 Uiso 1 1 calc R . .
H23B H 0.4757 0.1544 0.3298 0.050 Uiso 1 1 calc R . .
C24 C 0.33140(19) 0.14139(9) 0.41455(13) 0.0464(4) Uani 1 1 d . . .
C25 C 0.3160(3) 0.22855(15) 0.5449(2) 0.1000(9) Uani 1 1 d . . .
H25A H 0.2221 0.2477 0.4947 0.150 Uiso 1 1 calc R . .
H25B H 0.3749 0.2667 0.5908 0.150 Uiso 1 1 calc R . .
H25C H 0.2959 0.1925 0.5923 0.150 Uiso 1 1 calc R . .
N1 N 0.42427(15) 0.09284(7) 0.09261(10) 0.0437(3) Uani 1 1 d . . .
O1 O 0.02931(14) 0.12463(7) -0.04810(11) 0.0673(4) Uani 1 1 d . . .
O2 O 0.22520(17) 0.20881(7) 0.18827(11) 0.0702(4) Uani 1 1 d . . .
O3 O 0.33204(14) -0.06387(6) 0.22135(10) 0.0571(3) Uani 1 1 d . . .
O4 O 0.35354(15) -0.02796(7) 0.39464(10) 0.0625(4) Uani 1 1 d . . .
O5 O 0.20906(14) 0.11973(7) 0.40758(11) 0.0656(4) Uani 1 1 d . . .
O6 O 0.39901(15) 0.19666(8) 0.47996(12) 0.0722(4) Uani 1 1 d . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 118.68(17) . . ?
C6 C1 C7 123.01(16) . . ?
C2 C1 C7 118.29(16) . . ?
C3 C2 C1 120.3(2) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C4 C3 C2 120.4(2) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 120.1(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 C6 120.4(2) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 120.2(2) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
O1 C7 C1 122.71(15) . . ?
O1 C7 C8 116.76(16) . . ?
C1 C7 C8 120.49(14) . . ?
O2 C8 C9 122.71(15) . . ?
O2 C8 C7 119.59(15) . . ?
C9 C8 C7 117.24(14) . . ?
C8 C9 C10 113.35(13) . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9B 108.9 . . ?
C10 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C21 C10 C11 111.51(12) . . ?
C21 C10 C23 110.45(12) . . ?
C11 C10 C23 108.01(11) . . ?
C21 C10 C9 104.87(12) . . ?
C11 C10 C9 108.52(12) . . ?
C23 C10 C9 113.49(12) . . ?
N1 C11 C20 122.70(13) . . ?
N1 C11 C10 114.31(13) . . ?
C20 C11 C10 122.92(13) . . ?
C14 C13 N1 122.94(16) . . ?
C14 C13 H13 118.5 . . ?
N1 C13 H13 118.5 . . ?
C13 C14 C15 119.84(15) . . ?
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C16 122.92(16) . . ?
C14 C15 C20 118.17(15) . . ?
C16 C15 C20 118.90(17) . . ?
C17 C16 C15 121.15(17) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C18 120.37(18) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C19 C18 C17 120.46(19) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C20 120.88(16) . . ?
C18 C19 H19 119.6 . . ?
C20 C19 H19 119.6 . . ?
C19 C20 C15 118.18(14) . . ?
C19 C20 C11 124.78(14) . . ?
C15 C20 C11 117.03(14) . . ?
O4 C21 O3 124.05(15) . . ?
O4 C21 C10 125.27(15) . . ?
O3 C21 C10 110.64(12) . . ?
O3 C22 H22A 109.5 . . ?
O3 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O3 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 C10 118.21(13) . . ?
C24 C23 H23A 107.8 . . ?
C10 C23 H23A 107.8 . . ?
C24 C23 H23B 107.8 . . ?
C10 C23 H23B 107.8 . . ?
H23A C23 H23B 107.1 . . ?
O5 C24 O6 123.10(15) . . ?
O5 C24 C23 128.51(16) . . ?
O6 C24 C23 108.39(14) . . ?
O6 C25 H25A 109.5 . . ?
O6 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O6 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C11 N1 C13 119.26(14) . . ?
C21 O3 C22 116.38(14) . . ?
C24 O6 C25 115.59(15) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.383(2) . ?
C1 C2 1.387(2) . ?
C1 C7 1.483(2) . ?
C2 C3 1.379(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.361(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.367(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 O1 1.2112(19) . ?
C7 C8 1.526(2) . ?
C8 O2 1.2110(19) . ?
C8 C9 1.501(2) . ?
C9 C10 1.550(2) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C21 1.528(2) . ?
C10 C11 1.537(2) . ?
C10 C23 1.542(2) . ?
C11 N1 1.3119(19) . ?
C11 C20 1.426(2) . ?
C13 C14 1.342(2) . ?
C13 N1 1.364(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.410(2) . ?
C14 H14 0.9300 . ?
C15 C16 1.411(2) . ?
C15 C20 1.421(2) . ?
C16 C17 1.349(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.400(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.360(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.416(2) . ?
C19 H19 0.9300 . ?
C21 O4 1.1933(18) . ?
C21 O3 1.3306(19) . ?
C22 O3 1.446(2) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.497(2) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 O5 1.1945(19) . ?
C24 O6 1.332(2) . ?
C25 O6 1.442(2) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.6(3) . . . . ?
C7 C1 C2 C3 -177.95(16) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
C2 C3 C4 C5 -1.3(3) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
C4 C5 C6 C1 0.5(3) . . . . ?
C2 C1 C6 C5 -1.1(3) . . . . ?
C7 C1 C6 C5 177.34(18) . . . . ?
C6 C1 C7 O1 178.15(18) . . . . ?
C2 C1 C7 O1 -3.4(2) . . . . ?
C6 C1 C7 C8 0.4(2) . . . . ?
C2 C1 C7 C8 178.88(15) . . . . ?
O1 C7 C8 O2 -132.56(19) . . . . ?
C1 C7 C8 O2 45.3(2) . . . . ?
O1 C7 C8 C9 39.9(2) . . . . ?
C1 C7 C8 C9 -142.24(15) . . . . ?
O2 C8 C9 C10 -62.6(2) . . . . ?
C7 C8 C9 C10 125.15(15) . . . . ?
C8 C9 C10 C21 176.91(13) . . . . ?
C8 C9 C10 C11 -63.81(16) . . . . ?
C8 C9 C10 C23 56.27(17) . . . . ?
C21 C10 C11 N1 131.84(13) . . . . ?
C23 C10 C11 N1 -106.62(14) . . . . ?
C9 C10 C11 N1 16.81(17) . . . . ?
C21 C10 C11 C20 -51.15(18) . . . . ?
C23 C10 C11 C20 70.39(17) . . . . ?
C9 C10 C11 C20 -166.18(13) . . . . ?
N1 C13 C14 C15 -1.8(3) . . . . ?
C13 C14 C15 C16 -178.27(16) . . . . ?
C13 C14 C15 C20 0.3(2) . . . . ?
C14 C15 C16 C17 175.72(17) . . . . ?
C20 C15 C16 C17 -2.9(3) . . . . ?
C15 C16 C17 C18 1.9(3) . . . . ?
C16 C17 C18 C19 0.3(3) . . . . ?
C17 C18 C19 C20 -1.6(3) . . . . ?
C18 C19 C20 C15 0.6(2) . . . . ?
C18 C19 C20 C11 -178.21(16) . . . . ?
C14 C15 C20 C19 -177.09(14) . . . . ?
C16 C15 C20 C19 1.6(2) . . . . ?
C14 C15 C20 C11 1.8(2) . . . . ?
C16 C15 C20 C11 -179.51(14) . . . . ?
N1 C11 C20 C19 176.00(15) . . . . ?
C10 C11 C20 C19 -0.8(2) . . . . ?
N1 C11 C20 C15 -2.9(2) . . . . ?
C10 C11 C20 C15 -179.62(13) . . . . ?
C11 C10 C21 O4 137.11(16) . . . . ?
C23 C10 C21 O4 17.0(2) . . . . ?
C9 C10 C21 O4 -105.63(18) . . . . ?
C11 C10 C21 O3 -45.21(17) . . . . ?
C23 C10 C21 O3 -165.32(12) . . . . ?
C9 C10 C21 O3 72.05(15) . . . . ?
C21 C10 C23 C24 -76.53(17) . . . . ?
C11 C10 C23 C24 161.27(13) . . . . ?
C9 C10 C23 C24 40.90(19) . . . . ?
C10 C23 C24 O5 13.9(3) . . . . ?
C10 C23 C24 O6 -167.13(14) . . . . ?
C20 C11 N1 C13 1.6(2) . . . . ?
C10 C11 N1 C13 178.57(13) . . . . ?
C14 C13 N1 C11 0.8(2) . . . . ?
O4 C21 O3 C22 -1.7(2) . . . . ?
C10 C21 O3 C22 -179.38(14) . . . . ?
O5 C24 O6 C25 1.2(3) . . . . ?
C23 C24 O6 C25 -177.83(18) . . . . ?
