#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:06:14 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301780 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/67/1556795.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_1556795
loop_
_publ_author_name
'Aakeröy, Christer B'
'Spartz, Christine L.'
'Dembowski, Sean'
'Dwyre, Savannah'
'Desper, John'
_publ_section_title
;
 A systematic structural study of halogen bonding versus hydrogen bonding
 within competitive supramolecular systems.
;
_journal_issue                   'Pt 5'
_journal_name_full               IUCrJ
_journal_page_first              498
_journal_page_last               510
_journal_paper_doi               10.1107/S2052252515010854
_journal_volume                  2
_journal_year                    2015
_chemical_formula_moiety
;
(C12 H12 N2) (C7 H5 Br O2)2
;
_chemical_formula_sum            'C26 H22 Br2 N2 O4'
_chemical_formula_weight         586.28
_chemical_name_systematic
;
SD-1--27-6--5 1,2-bis(4-pyridyl)ethane, (4-Br-PhCOOH)2
;
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                93.434(2)
_cell_angle_beta                 94.022(2)
_cell_angle_gamma                103.373(2)
_cell_formula_units_Z            1
_cell_length_a                   7.1108(4)
_cell_length_b                   7.4624(4)
_cell_length_c                   11.2299(6)
_cell_measurement_reflns_used    6775
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      32.94
_cell_measurement_theta_min      2.81
_cell_volume                     576.53(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.942
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_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  0.0349
_diffrn_reflns_av_sigmaI/netI    0.0387
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13290
_diffrn_reflns_theta_full        32.50
_diffrn_reflns_theta_max         33.16
_diffrn_reflns_theta_min         1.82
_exptl_absorpt_coefficient_mu    3.553
_exptl_absorpt_correction_T_max  0.8151
_exptl_absorpt_correction_T_min  0.3780
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             294
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.771
_refine_diff_density_min         -1.014
_refine_diff_density_rms         0.112
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     157
_refine_ls_number_reflns         4144
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0529
_refine_ls_R_factor_gt           0.0388
_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)+(0.0650P)²+0.2000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0986
_refine_ls_wR_factor_ref         0.1065
_reflns_number_gt                3417
_reflns_number_total             4144
_reflns_threshold_expression     >2sigma(I)
_publcif_datablock.id            {ea6a6c31-9d2a-4fe2-8628-1fdb90ffe50b}
_cod_data_source_file            lc5065.cif
_cod_data_source_block           BrCO11
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_symmetry_cell_setting' value 'Triclinic' was changed to
'triclinic' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/IUCr/depositions/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 
;
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1556795
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N11 N 0.2019(3) 0.9603(2) 0.36740(17) 0.0222(3) Uani 1 1 d .
C12 C 0.3794(3) 0.9729(3) 0.3303(2) 0.0229(4) Uani 1 1 d .
H12 H 0.4292 1.0683 0.2806 0.027 Uiso 1 1 calc R
C13 C 0.4924(3) 0.8527(3) 0.36146(19) 0.0207(4) Uani 1 1 d .
H13 H 0.6174 0.8661 0.3332 0.025 Uiso 1 1 calc R
C14 C 0.4231(3) 0.7114(3) 0.43455(18) 0.0192(3) Uani 1 1 d .
C15 C 0.2396(3) 0.6999(3) 0.47291(19) 0.0220(4) Uani 1 1 d .
H15 H 0.1863 0.6067 0.5233 0.026 Uiso 1 1 calc R
C16 C 0.1345(3) 0.8254(3) 0.4371(2) 0.0234(4) Uani 1 1 d .
H16 H 0.0087 0.8149 0.4636 0.028 Uiso 1 1 calc R
C17 C 0.5495(3) 0.5830(3) 0.46874(19) 0.0209(4) Uani 1 1 d .
H17A H 0.6624 0.6542 0.5219 0.025 Uiso 1 1 calc R
H17B H 0.5996 0.5385 0.3953 0.025 Uiso 1 1 calc R
Br1 Br -0.34658(3) 1.87116(3) 0.04548(2) 0.02855(9) Uani 1 1 d .
C21 C -0.0148(3) 1.4482(3) 0.18747(17) 0.0179(3) Uani 1 1 d .
C27 C 0.0972(3) 1.3182(3) 0.23586(18) 0.0189(3) Uani 1 1 d .
O21 O -0.0107(2) 1.1762(2) 0.28247(16) 0.0276(3) Uani 1 1 d .
H21 H 0.053(5) 1.102(5) 0.306(3) 0.033 Uiso 1 1 d .
O22 O 0.2719(2) 1.3448(2) 0.23445(16) 0.0282(3) Uani 1 1 d .
C22 C 0.0858(3) 1.6105(3) 0.14412(19) 0.0208(4) Uani 1 1 d .
H22 H 0.2230 1.6349 0.1440 0.025 Uiso 1 1 calc R
C23 C -0.0119(3) 1.7364(3) 0.10132(19) 0.0222(4) Uani 1 1 d .
H23 H 0.0567 1.8477 0.0721 0.027 Uiso 1 1 calc R
C24 C -0.2122(3) 1.6972(3) 0.10176(19) 0.0205(4) Uani 1 1 d .
C25 C -0.3165(3) 1.5356(3) 0.1423(2) 0.0232(4) Uani 1 1 d .
H25 H -0.4539 1.5106 0.1408 0.028 Uiso 1 1 calc R
C26 C -0.2160(3) 1.4107(3) 0.1853(2) 0.0218(4) Uani 1 1 d .
H26 H -0.2851 1.2988 0.2135 0.026 Uiso 1 1 calc R
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'
O O 0.0106 0.0060 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C16 N11 C12 117.79(18) . .
N11 C12 C13 122.58(19) . .
N11 C12 H12 118.7 . .
C13 C12 H12 118.7 . .
C12 C13 C14 119.98(18) . .
C12 C13 H13 120.0 . .
C14 C13 H13 120.0 . .
C15 C14 C13 117.03(17) . .
C15 C14 C17 123.78(18) . .
C13 C14 C17 119.18(17) . .
C16 C15 C14 119.52(19) . .
C16 C15 H15 120.2 . .
C14 C15 H15 120.2 . .
N11 C16 C15 123.10(19) . .
N11 C16 H16 118.5 . .
C15 C16 H16 118.5 . .
C14 C17 C17 115.1(2) . 2_666
C14 C17 H17A 108.5 . .
C17 C17 H17A 108.5 2_666 .
C14 C17 H17B 108.5 . .
C17 C17 H17B 108.5 2_666 .
H17A C17 H17B 107.5 . .
C26 C21 C22 119.69(18) . .
C26 C21 C27 121.56(17) . .
C22 C21 C27 118.75(17) . .
O22 C27 O21 123.69(18) . .
O22 C27 C21 122.62(18) . .
O21 C27 C21 113.68(16) . .
C27 O21 H21 112(2) . .
C23 C22 C21 120.55(18) . .
C23 C22 H22 119.7 . .
C21 C22 H22 119.7 . .
C22 C23 C24 118.67(18) . .
C22 C23 H23 120.7 . .
C24 C23 H23 120.7 . .
C25 C24 C23 122.08(18) . .
C25 C24 Br1 119.08(14) . .
C23 C24 Br1 118.83(15) . .
C24 C25 C26 118.53(18) . .
C24 C25 H25 120.7 . .
C26 C25 H25 120.7 . .
C25 C26 C21 120.45(18) . .
C25 C26 H26 119.8 . .
C21 C26 H26 119.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N11 C16 1.334(3) .
N11 C12 1.341(3) .
C12 C13 1.380(3) .
C12 H12 0.9500 .
C13 C14 1.396(3) .
C13 H13 0.9500 .
C14 C15 1.388(3) .
C14 C17 1.506(3) .
C15 C16 1.387(3) .
C15 H15 0.9500 .
C16 H16 0.9500 .
C17 C17 1.515(4) 2_666
C17 H17A 0.9900 .
C17 H17B 0.9900 .
Br1 C24 1.8934(19) .
C21 C26 1.391(3) .
C21 C22 1.391(3) .
C21 C27 1.493(3) .
C27 O22 1.213(2) .
C27 O21 1.316(2) .
O21 H21 0.83(4) .
C22 C23 1.381(3) .
C22 H22 0.9500 .
C23 C24 1.387(3) .
C23 H23 0.9500 .
C24 C25 1.382(3) .
C25 C26 1.388(3) .
C25 H25 0.9500 .
C26 H26 0.9500 .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O21 H21 N11 0.83(4) 1.80(4) 2.626(2) 174(3)
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_4
C16 N11 C12 C13 0.0(3) .
N11 C12 C13 C14 -0.1(3) .
C12 C13 C14 C15 -0.1(3) .
C12 C13 C14 C17 -179.29(19) .
C13 C14 C15 C16 0.5(3) .
C17 C14 C15 C16 179.58(19) .
C12 N11 C16 C15 0.3(3) .
C14 C15 C16 N11 -0.6(3) .
C15 C14 C17 C17 10.2(3) 2_666
C13 C14 C17 C17 -170.7(2) 2_666
C26 C21 C27 O22 177.2(2) .
C22 C21 C27 O22 -3.1(3) .
C26 C21 C27 O21 -4.5(3) .
C22 C21 C27 O21 175.25(19) .
C26 C21 C22 C23 1.4(3) .
C27 C21 C22 C23 -178.41(19) .
C21 C22 C23 C24 -0.4(3) .
C22 C23 C24 C25 -0.7(3) .
C22 C23 C24 Br1 179.03(16) .
C23 C24 C25 C26 0.9(3) .
Br1 C24 C25 C26 -178.87(16) .
C24 C25 C26 C21 0.1(3) .
C22 C21 C26 C25 -1.2(3) .
C27 C21 C26 C25 178.57(19) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168305954
