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#$Date: 2024-07-05 20:37:31 +0300 (Fri, 05 Jul 2024) $
#$Revision: 293195 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/32/7063256.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_7063256
loop_
_publ_author_name
'Yang, Jing'
'Hu, Xing-Mei'
'Zhao, Ke-Hua'
'Huang, Kun'
'Yan, Sheng-Jiao'
_publ_section_title
;
 Cu(ii)-catalyzed annulation of α,β-unsaturated ketoxime acetates with
 3-formylchromones for the synthesis of functionalized 2,4-diarylpyridines
;
_journal_issue                   26
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              11682
_journal_page_last               11687
_journal_paper_doi               10.1039/D4NJ01648C
_journal_volume                  48
_journal_year                    2024
_chemical_formula_moiety         'C20 H15 Br2 N3 O2 S'
_chemical_formula_sum            'C20 H15 Br2 N3 O2 S'
_chemical_formula_weight         521.23
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2023-05-05
_audit_creation_method
;
FinalCif V88 by Daniel Kratzert, Freiburg 2023,
https://github.com/dkratzert/FinalCif
;
_audit_update_record
;
2023-12-24 deposited with the CCDC.	2024-06-05 downloaded from the CCDC.
;
_cell_angle_alpha                97.903(2)
_cell_angle_beta                 99.085(2)
_cell_angle_gamma                99.491(2)
_cell_formula_units_Z            2
_cell_length_a                   7.8970(5)
_cell_length_b                   10.6539(6)
_cell_length_c                   14.6586(8)
_cell_measurement_reflns_used    9964
_cell_measurement_temperature    100.00
_cell_measurement_theta_max      28.32
_cell_measurement_theta_min      2.23
_cell_volume                     1184.09(12)
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (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      100.00
_diffrn_detector                 CPAD
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE dual wavelength Mo/Cu'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_measurement_specimen_support 'MiTeGen micromount'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            34239
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.366
_diffrn_reflns_theta_min         2.661
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_type              'Incoatec I\ms'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.529
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.5731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1217 before and 0.0512 after correction.
The Ratio of minimum to maximum transmission is 0.7685.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_description       block
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.078
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         5933
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0372
_refine_ls_R_factor_gt           0.0288
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0328P)²+0.6548P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0682
_refine_ls_wR_factor_ref         0.0709
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4998
_reflns_number_total             5933
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4nj01648c2.cif
_cod_data_source_block           1_sq
_cod_depositor_comments          'Adding full bibliography for 7063256.cif.'
_cod_database_code               7063256
_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 N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), C2(H2), C3(H3A), C5(H5), C6(H6), C16(H16), C17(H17), C19(H19), C20(H20)
;
_olex2_submission_special_instructions 'No special instructions were received'
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_estimated_absorpt_t_min   0.438
_shelx_estimated_absorpt_t_max   0.539
_olex2_diffrn_ambient_temperature_device 'Oxford Cryostream 800'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 1.04144(3) 0.85109(2) 1.34748(2) 0.02434(6) Uani 1 1 d . . . . .
Br2 Br 0.76170(3) 0.07661(2) 0.40137(2) 0.02207(6) Uani 1 1 d . . . . .
S003 S 0.51277(7) 0.47397(5) 0.74555(4) 0.01838(11) Uani 1 1 d . . . . .
O1 O 0.7568(2) 0.52351(17) 0.89746(11) 0.0267(4) Uani 1 1 d . . . . .
O2 O 0.13353(18) 0.40483(15) 0.51982(10) 0.0191(3) Uani 1 1 d . . . . .
N1 N 0.5174(2) 0.61546(18) 0.91884(12) 0.0190(4) Uani 1 1 d . . . . .
N2 N 0.2793(2) 0.59282(18) 0.79889(12) 0.0169(4) Uani 1 1 d . . . . .
N3 N 0.0611(2) 0.56700(19) 0.66559(12) 0.0205(4) Uani 1 1 d . . . . .
H3 H 0.020062 0.532242 0.606570 0.025 Uiso 1 1 calc R U . . .
C1 C 0.9320(3) 0.7721(2) 1.22365(15) 0.0198(4) Uani 1 1 d . . . . .
C2 C 1.0255(3) 0.7087(2) 1.16641(15) 0.0220(5) Uani 1 1 d . . . . .
H2 H 1.144164 0.705120 1.188233 0.026 Uiso 1 1 calc R U . . .
C3 C 0.9419(3) 0.6500(2) 1.07596(15) 0.0203(4) Uani 1 1 d . . . . .
H3A H 1.004414 0.606090 1.035749 0.024 Uiso 1 1 calc R U . . .
C4 C 0.7678(3) 0.6551(2) 1.04380(14) 0.0180(4) Uani 1 1 d . . . . .
C5 C 0.6770(3) 0.7180(2) 1.10370(15) 0.0220(5) Uani 1 1 d . . . . .
H5 H 0.557676 0.720541 1.082664 0.026 Uiso 1 1 calc R U . . .
C6 C 0.7585(3) 0.7773(2) 1.19405(15) 0.0228(5) Uani 1 1 d . . . . .
H6 H 0.696068 0.820566 1.234704 0.027 Uiso 1 1 calc R U . . .
C7 C 0.6818(3) 0.5903(2) 0.94686(14) 0.0193(4) Uani 1 1 d . . . . .
C8 C 0.4400(3) 0.5669(2) 0.83243(14) 0.0176(4) Uani 1 1 d . . . . .
C9 C 0.1827(3) 0.6673(2) 0.85721(15) 0.0217(5) Uani 1 1 d . . . . .
H9A H 0.265467 0.728712 0.907964 0.026 Uiso 1 1 calc R U . . .
H9B H 0.104865 0.608390 0.886145 0.026 Uiso 1 1 calc R U . . .
C10 C 0.0758(3) 0.7402(2) 0.79589(16) 0.0254(5) Uani 1 1 d . . . . .
H10A H 0.154833 0.805042 0.772189 0.031 Uiso 1 1 calc R U . . .
H10B H 0.003864 0.786185 0.833266 0.031 Uiso 1 1 calc R U . . .
C11 C -0.0418(3) 0.6472(3) 0.71398(16) 0.0272(5) Uani 1 1 d . . . . .
H11A H -0.133575 0.591669 0.736985 0.033 Uiso 1 1 calc R U . . .
H11B H -0.099649 0.696371 0.669837 0.033 Uiso 1 1 calc R U . . .
C12 C 0.2134(3) 0.5436(2) 0.70585(14) 0.0171(4) Uani 1 1 d . . . . .
C13 C 0.3234(3) 0.4736(2) 0.66363(14) 0.0173(4) Uani 1 1 d . . . . .
C14 C 0.2765(3) 0.4035(2) 0.57030(14) 0.0166(4) Uani 1 1 d . . . . .
C15 C 0.3978(3) 0.3255(2) 0.53218(14) 0.0154(4) Uani 1 1 d . . . . .
C16 C 0.5776(3) 0.3723(2) 0.54428(14) 0.0165(4) Uani 1 1 d . . . . .
H16 H 0.626608 0.455145 0.580367 0.020 Uiso 1 1 calc R U . . .
C17 C 0.6851(3) 0.2992(2) 0.50416(14) 0.0172(4) Uani 1 1 d . . . . .
H17 H 0.806707 0.332043 0.511358 0.021 Uiso 1 1 calc R U . . .
C18 C 0.6131(3) 0.1785(2) 0.45389(15) 0.0180(4) Uani 1 1 d . . . . .
C19 C 0.4355(3) 0.1281(2) 0.44082(15) 0.0212(4) Uani 1 1 d . . . . .
H19 H 0.388689 0.043763 0.406696 0.025 Uiso 1 1 calc R U . . .
C20 C 0.3280(3) 0.2035(2) 0.47869(15) 0.0197(4) Uani 1 1 d . . . . .
H20 H 0.205653 0.171915 0.468137 0.024 Uiso 1 1 calc R U . . .
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'
Br Br -0.2901 2.4595 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 '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
C8 S003 C13 91.39(10) . . ?
C8 N1 C7 116.62(18) . . ?
C8 N2 C9 123.06(17) . . ?
C8 N2 C12 115.16(17) . . ?
C12 N2 C9 121.78(17) . . ?
C11 N3 H3 118.2 . . ?
C12 N3 H3 118.2 . . ?
C12 N3 C11 123.65(18) . . ?
C2 C1 Br1 119.52(16) . . ?
C2 C1 C6 121.9(2) . . ?
C6 C1 Br1 118.59(17) . . ?
C1 C2 H2 120.7 . . ?
C1 C2 C3 118.58(19) . . ?
C3 C2 H2 120.7 . . ?
C2 C3 H3A 119.6 . . ?
C4 C3 C2 120.8(2) . . ?
C4 C3 H3A 119.6 . . ?
C3 C4 C7 119.45(19) . . ?
C5 C4 C3 119.07(19) . . ?
C5 C4 C7 121.46(19) . . ?
C4 C5 H5 119.6 . . ?
C4 C5 C6 120.9(2) . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 118.8(2) . . ?
C1 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
O1 C7 N1 124.61(19) . . ?
O1 C7 C4 121.27(19) . . ?
N1 C7 C4 114.09(18) . . ?
N1 C8 S003 129.74(16) . . ?
N1 C8 N2 119.56(19) . . ?
N2 C8 S003 110.66(15) . . ?
N2 C9 H9A 110.0 . . ?
N2 C9 H9B 110.0 . . ?
N2 C9 C10 108.66(17) . . ?
H9A C9 H9B 108.3 . . ?
C10 C9 H9A 110.0 . . ?
C10 C9 H9B 110.0 . . ?
C9 C10 H10A 109.6 . . ?
C9 C10 H10B 109.6 . . ?
C9 C10 C11 110.1(2) . . ?
H10A C10 H10B 108.1 . . ?
C11 C10 H10A 109.6 . . ?
C11 C10 H10B 109.6 . . ?
N3 C11 C10 109.95(18) . . ?
N3 C11 H11A 109.7 . . ?
N3 C11 H11B 109.7 . . ?
C10 C11 H11A 109.7 . . ?
C10 C11 H11B 109.7 . . ?
H11A C11 H11B 108.2 . . ?
N2 C12 C13 112.81(17) . . ?
N3 C12 N2 119.94(19) . . ?
N3 C12 C13 127.24(19) . . ?
C12 C13 S003 109.98(15) . . ?
C12 C13 C14 123.19(18) . . ?
C14 C13 S003 126.58(16) . . ?
O2 C14 C13 121.08(19) . . ?
O2 C14 C15 119.10(18) . . ?
C13 C14 C15 119.82(18) . . ?
C16 C15 C14 122.42(19) . . ?
C20 C15 C14 118.69(18) . . ?
C20 C15 C16 118.82(19) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 C15 120.7(2) . . ?
C17 C16 H16 119.6 . . ?
C16 C17 H17 120.5 . . ?
C18 C17 C16 118.98(19) . . ?
C18 C17 H17 120.5 . . ?
C17 C18 Br2 118.93(16) . . ?
C17 C18 C19 122.1(2) . . ?
C19 C18 Br2 119.00(16) . . ?
C18 C19 H19 120.7 . . ?
C20 C19 C18 118.6(2) . . ?
C20 C19 H19 120.7 . . ?
C15 C20 H20 119.6 . . ?
C19 C20 C15 120.8(2) . . ?
C19 C20 H20 119.6 . . ?
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
Br1 C1 1.896(2) . ?
Br2 C18 1.904(2) . ?
S003 C8 1.733(2) . ?
S003 C13 1.763(2) . ?
O1 C7 1.230(3) . ?
O2 C14 1.252(2) . ?
N1 C7 1.379(3) . ?
N1 C8 1.310(3) . ?
N2 C8 1.372(3) . ?
N2 C9 1.470(3) . ?
N2 C12 1.377(3) . ?
N3 H3 0.8800 . ?
N3 C11 1.462(3) . ?
N3 C12 1.331(3) . ?
C1 C2 1.382(3) . ?
C1 C6 1.383(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.394(3) . ?
C3 H3A 0.9500 . ?
C3 C4 1.393(3) . ?
C4 C5 1.389(3) . ?
C4 C7 1.493(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.391(3) . ?
C6 H6 0.9500 . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.514(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C10 C11 1.517(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.397(3) . ?
C13 C14 1.426(3) . ?
C14 C15 1.491(3) . ?
C15 C16 1.400(3) . ?
C15 C20 1.398(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.387(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.373(3) . ?
C18 C19 1.390(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.388(3) . ?
C20 H20 0.9500 . ?
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
Br1 C1 C2 C3 179.30(17) . . . . ?
Br1 C1 C6 C5 -179.16(18) . . . . ?
Br2 C18 C19 C20 -179.46(16) . . . . ?
S003 C13 C14 O2 175.96(16) . . . . ?
S003 C13 C14 C15 -3.1(3) . . . . ?
O2 C14 C15 C16 136.2(2) . . . . ?
O2 C14 C15 C20 -40.7(3) . . . . ?
N2 C9 C10 C11 55.5(3) . . . . ?
N2 C12 C13 S003 -0.5(2) . . . . ?
N2 C12 C13 C14 174.08(19) . . . . ?
N3 C12 C13 S003 178.28(19) . . . . ?
N3 C12 C13 C14 -7.1(4) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C1 C6 C5 -0.7(4) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C2 C3 C4 C7 -179.5(2) . . . . ?
C3 C4 C5 C6 1.1(3) . . . . ?
C3 C4 C7 O1 6.1(3) . . . . ?
C3 C4 C7 N1 -172.2(2) . . . . ?
C4 C5 C6 C1 -0.3(4) . . . . ?
C5 C4 C7 O1 -172.4(2) . . . . ?
C5 C4 C7 N1 9.3(3) . . . . ?
C6 C1 C2 C3 0.9(4) . . . . ?
C7 N1 C8 S003 -0.1(3) . . . . ?
C7 N1 C8 N2 -177.27(19) . . . . ?
C7 C4 C5 C6 179.6(2) . . . . ?
C8 S003 C13 C12 -0.14(17) . . . . ?
C8 S003 C13 C14 -174.5(2) . . . . ?
C8 N1 C7 O1 -2.0(3) . . . . ?
C8 N1 C7 C4 176.27(19) . . . . ?
C8 N2 C9 C10 148.5(2) . . . . ?
C8 N2 C12 N3 -177.7(2) . . . . ?
C8 N2 C12 C13 1.2(3) . . . . ?
C9 N2 C8 S003 178.57(17) . . . . ?
C9 N2 C8 N1 -3.7(3) . . . . ?
C9 N2 C12 N3 2.4(3) . . . . ?
C9 N2 C12 C13 -178.65(19) . . . . ?
C9 C10 C11 N3 -52.0(3) . . . . ?
C11 N3 C12 N2 2.1(3) . . . . ?
C11 N3 C12 C13 -176.7(2) . . . . ?
C12 N2 C8 S003 -1.3(2) . . . . ?
C12 N2 C8 N1 176.43(19) . . . . ?
C12 N2 C9 C10 -31.7(3) . . . . ?
C12 N3 C11 C10 23.5(3) . . . . ?
C12 C13 C14 O2 2.3(3) . . . . ?
C12 C13 C14 C15 -176.8(2) . . . . ?
C13 S003 C8 N1 -176.6(2) . . . . ?
C13 S003 C8 N2 0.78(17) . . . . ?
C13 C14 C15 C16 -44.7(3) . . . . ?
C13 C14 C15 C20 138.4(2) . . . . ?
C14 C15 C16 C17 -177.04(19) . . . . ?
C14 C15 C20 C19 179.21(19) . . . . ?
C15 C16 C17 C18 -1.4(3) . . . . ?
C16 C15 C20 C19 2.2(3) . . . . ?
C16 C17 C18 Br2 -178.53(15) . . . . ?
C16 C17 C18 C19 0.9(3) . . . . ?
C17 C18 C19 C20 1.1(3) . . . . ?
C18 C19 C20 C15 -2.7(3) . . . . ?
C20 C15 C16 C17 -0.1(3) . . . . ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.296 0.000 0.000 310.0 88.0 ?
