#------------------------------------------------------------------------------
#$Date: 2025-08-19 15:18:28 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301805 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/70/2227036.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2227036
loop_
_publ_author_name
'Li, Si-Si'
'Zhang, Bei'
'Zhang, Hong-Lin'
_publ_section_title
;
 5,8-Dibromo-2,11-dithia[3,3](2,6)pyridinoparacyclophane
;
_journal_coeditor_code           PK2253
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2125
_journal_paper_doi               10.1107/S1600536810028850
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C15 H13 Br2 N S2'
_chemical_formula_moiety         'C15 H13 Br2 N S2'
_chemical_formula_sum            'C15 H13 Br2 N S2'
_chemical_formula_weight         431.20
_chemical_name_common
;
5,8-Dibromo-2,11-dithia[3,3](2,6)pyridinoparacyclophane
;
_chemical_name_systematic
;
1²,1⁵-dibromo-2,7-dithia-1(1,4)-benzena-5(2,6)-pyridinaoctaphane
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 103.878(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.9275(15)
_cell_length_b                   18.879(3)
_cell_length_c                   9.3213(15)
_cell_measurement_reflns_used    4039
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      27.81
_cell_measurement_theta_min      2.50
_cell_volume                     1525.2(4)
_computing_cell_refinement       'SAINT (Bruker, 1999)'
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and 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  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0301
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            11428
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         2.16
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    5.577
_exptl_absorpt_correction_T_max  0.573
_exptl_absorpt_correction_T_min  0.452
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.878
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.559
_refine_diff_density_min         -0.460
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         3775
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0313
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0414P)²+0.2049P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0737
_refine_ls_wR_factor_ref         0.0781
_reflns_number_gt                3018
_reflns_number_total             3775
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pk2253.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2227036
_cod_database_fobs_code          2227036
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_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1 0.63099(3) 0.048688(14) 0.87832(3) 0.04897(10) Uani d . 1 . .
Br Br2 0.22924(4) 0.139645(16) 0.22281(3) 0.05124(10) Uani d . 1 . .
C C1 0.3799(3) 0.03373(12) 0.6206(3) 0.0338(5) Uani d . 1 . .
C C2 0.5079(3) 0.07344(12) 0.6886(3) 0.0334(5) Uani d . 1 . .
C C3 0.5520(3) 0.13348(12) 0.6246(3) 0.0331(5) Uani d . 1 . .
H H3 0.6384 0.1587 0.6742 0.040 Uiso calc R 1 . .
C C4 0.4686(3) 0.15680(13) 0.4867(3) 0.0324(5) Uani d . 1 . .
C C5 0.3444(3) 0.11522(13) 0.4148(3) 0.0338(5) Uani d . 1 . .
C C6 0.3002(3) 0.05574(12) 0.4802(3) 0.0372(5) Uani d . 1 . .
H H6 0.2154 0.0298 0.4295 0.045 Uiso calc R 1 . .
C C7 0.5137(3) 0.22521(13) 0.4279(3) 0.0383(6) Uani d . 1 . .
H H7A 0.5180 0.2181 0.3259 0.046 Uiso calc R 1 . .
H H7B 0.6168 0.2376 0.4835 0.046 Uiso calc R 1 . .
C C8 0.3410(3) 0.28873(14) 0.6143(3) 0.0371(5) Uani d . 1 . .
H H8A 0.4332 0.2727 0.6849 0.045 Uiso calc R 1 . .
H H8B 0.3134 0.3346 0.6471 0.045 Uiso calc R 1 . .
C C9 0.2123(3) 0.23745(12) 0.6156(2) 0.0301(5) Uani d . 1 . .
C C10 0.0700(3) 0.24389(14) 0.5179(3) 0.0382(5) Uani d . 1 . .
H H10 0.0501 0.2810 0.4505 0.046 Uiso calc R 1 . .
C C11 -0.0417(3) 0.19455(15) 0.5220(3) 0.0414(6) Uani d . 1 . .
H H11 -0.1389 0.1982 0.4580 0.050 Uiso calc R 1 . .
C C12 -0.0085(3) 0.13961(13) 0.6216(3) 0.0387(6) Uani d . 1 . .
H H12 -0.0819 0.1050 0.6243 0.046 Uiso calc R 1 . .
C C13 0.1362(3) 0.13660(11) 0.7180(3) 0.0308(5) Uani d . 1 . .
C C14 0.1781(3) 0.07834(13) 0.8309(3) 0.0384(6) Uani d . 1 . .
H H14A 0.1171 0.0840 0.9034 0.046 Uiso calc R 1 . .
H H14B 0.2858 0.0835 0.8820 0.046 Uiso calc R 1 . .
C C15 0.3230(3) -0.02833(13) 0.6927(3) 0.0426(6) Uani d . 1 . .
H H15A 0.4036 -0.0430 0.7770 0.051 Uiso calc R 1 . .
H H15B 0.3036 -0.0674 0.6232 0.051 Uiso calc R 1 . .
N N1 0.2443(2) 0.18540(10) 0.7172(2) 0.0302(4) Uani d . 1 . .
S S1 0.14839(8) -0.01069(3) 0.75438(8) 0.04531(17) Uani d . 1 . .
S S2 0.38563(7) 0.29931(3) 0.43559(7) 0.03722(15) Uani d . 1 . .
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'
N N 0.0061 0.0033 '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'
Br Br -0.2901 2.4595 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 116.5(2) ?
C2 C1 C15 . . 123.3(2) ?
C6 C1 C15 . . 120.2(2) ?
C3 C2 C1 . . 122.4(2) ?
C3 C2 Br1 . . 116.22(18) ?
C1 C2 Br1 . . 121.40(18) ?
C2 C3 C4 . . 120.9(2) ?
C2 C3 H3 . . 119.6 ?
C4 C3 H3 . . 119.6 ?
C5 C4 C3 . . 117.0(2) ?
C5 C4 C7 . . 124.3(2) ?
C3 C4 C7 . . 118.6(2) ?
C6 C5 C4 . . 121.7(2) ?
C6 C5 Br2 . . 117.85(18) ?
C4 C5 Br2 . . 120.44(19) ?
C5 C6 C1 . . 121.4(2) ?
C5 C6 H6 . . 119.3 ?
C1 C6 H6 . . 119.3 ?
C4 C7 S2 . . 115.00(17) ?
C4 C7 H7A . . 108.5 ?
S2 C7 H7A . . 108.5 ?
C4 C7 H7B . . 108.5 ?
S2 C7 H7B . . 108.5 ?
H7A C7 H7B . . 107.5 ?
C9 C8 S2 . . 114.50(16) ?
C9 C8 H8A . . 108.6 ?
S2 C8 H8A . . 108.6 ?
C9 C8 H8B . . 108.6 ?
S2 C8 H8B . . 108.6 ?
H8A C8 H8B . . 107.6 ?
N1 C9 C10 . . 122.3(2) ?
N1 C9 C8 . . 116.2(2) ?
C10 C9 C8 . . 121.5(2) ?
C11 C10 C9 . . 118.9(2) ?
C11 C10 H10 . . 120.6 ?
C9 C10 H10 . . 120.6 ?
C10 C11 C12 . . 119.3(2) ?
C10 C11 H11 . . 120.3 ?
C12 C11 H11 . . 120.3 ?
C11 C12 C13 . . 119.0(2) ?
C11 C12 H12 . . 120.5 ?
C13 C12 H12 . . 120.5 ?
N1 C13 C12 . . 122.0(2) ?
N1 C13 C14 . . 116.7(2) ?
C12 C13 C14 . . 121.3(2) ?
C13 C14 S1 . . 114.34(18) ?
C13 C14 H14A . . 108.7 ?
S1 C14 H14A . . 108.7 ?
C13 C14 H14B . . 108.7 ?
S1 C14 H14B . . 108.7 ?
H14A C14 H14B . . 107.6 ?
C1 C15 S1 . . 114.02(17) ?
C1 C15 H15A . . 108.7 ?
S1 C15 H15A . . 108.7 ?
C1 C15 H15B . . 108.7 ?
S1 C15 H15B . . 108.7 ?
H15A C15 H15B . . 107.6 ?
C13 N1 C9 . . 118.4(2) ?
C15 S1 C14 . . 103.75(12) ?
C8 S2 C7 . . 103.29(12) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1 C2 . 1.903(2) ?
Br2 C5 . 1.895(2) ?
C1 C2 . 1.386(3) ?
C1 C6 . 1.395(3) ?
C1 C15 . 1.498(4) ?
C2 C3 . 1.381(3) ?
C3 C4 . 1.393(3) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.392(3) ?
C4 C7 . 1.496(3) ?
C5 C6 . 1.380(3) ?
C6 H6 . 0.9300 ?
C7 S2 . 1.819(3) ?
C7 H7A . 0.9700 ?
C7 H7B . 0.9700 ?
C8 C9 . 1.505(3) ?
C8 S2 . 1.814(2) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 N1 . 1.347(3) ?
C9 C10 . 1.379(3) ?
C10 C11 . 1.371(4) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.377(4) ?
C11 H11 . 0.9300 ?
C12 C13 . 1.386(3) ?
C12 H12 . 0.9300 ?
C13 N1 . 1.335(3) ?
C13 C14 . 1.506(3) ?
C14 S1 . 1.820(3) ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C15 S1 . 1.817(3) ?
C15 H15A . 0.9700 ?
C15 H15B . 0.9700 ?
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . 2.6(3) ?
C15 C1 C2 C3 . . . . -175.3(2) ?
C6 C1 C2 Br1 . . . . -178.55(17) ?
C15 C1 C2 Br1 . . . . 3.6(3) ?
C1 C2 C3 C4 . . . . -0.2(4) ?
Br1 C2 C3 C4 . . . . -179.17(17) ?
C2 C3 C4 C5 . . . . -2.8(3) ?
C2 C3 C4 C7 . . . . 175.2(2) ?
C3 C4 C5 C6 . . . . 3.5(3) ?
C7 C4 C5 C6 . . . . -174.3(2) ?
C3 C4 C5 Br2 . . . . -177.02(16) ?
C7 C4 C5 Br2 . . . . 5.1(3) ?
C4 C5 C6 C1 . . . . -1.2(4) ?
Br2 C5 C6 C1 . . . . 179.31(18) ?
C2 C1 C6 C5 . . . . -1.8(3) ?
C15 C1 C6 C5 . . . . 176.1(2) ?
C5 C4 C7 S2 . . . . 72.8(3) ?
C3 C4 C7 S2 . . . . -105.0(2) ?
S2 C8 C9 N1 . . . . 126.56(19) ?
S2 C8 C9 C10 . . . . -53.5(3) ?
N1 C9 C10 C11 . . . . -1.6(4) ?
C8 C9 C10 C11 . . . . 178.4(2) ?
C9 C10 C11 C12 . . . . -0.8(4) ?
C10 C11 C12 C13 . . . . 1.5(4) ?
C11 C12 C13 N1 . . . . 0.1(4) ?
C11 C12 C13 C14 . . . . 179.1(2) ?
N1 C13 C14 S1 . . . . -126.8(2) ?
C12 C13 C14 S1 . . . . 54.2(3) ?
C2 C1 C15 S1 . . . . 105.8(2) ?
C6 C1 C15 S1 . . . . -71.9(3) ?
C12 C13 N1 C9 . . . . -2.4(3) ?
C14 C13 N1 C9 . . . . 178.6(2) ?
C10 C9 N1 C13 . . . . 3.2(3) ?
C8 C9 N1 C13 . . . . -176.80(19) ?
C1 C15 S1 C14 . . . . -40.3(2) ?
C13 C14 S1 C15 . . . . 83.7(2) ?
C9 C8 S2 C7 . . . . -83.4(2) ?
C4 C7 S2 C8 . . . . 40.9(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745614
2 PubChem 139079398
