#------------------------------------------------------------------------------
#$Date: 2025-08-22 17:55:42 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301864 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/21/81/7218145.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_7218145
loop_
_publ_author_name
'Wang, Lei'
'Hu, Yanjing'
'Xu, Wenyan'
'pang, Yanyan'
'Liu, Faqian'
'Yang, Yu'
_publ_section_title
;
 Investigation of Hydrogen Bonding Patterns in A Series of Multi-component
 Molecular Solids Formed by Tetrabromoterephthalic Acid with Selected
 N-heterocycles
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C4RA08452G
_journal_year                    2014
_chemical_formula_moiety         '2(C8 H2 Br4 O4), Br4 C8 O4, 2(C5 H9 N2)'
_chemical_formula_sum            'C34 H22 Br12 N4 O12'
_chemical_formula_weight         1637.36
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2014-09-04
_audit_creation_method
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_cell_angle_alpha                106.546(3)
_cell_angle_beta                 106.524(4)
_cell_angle_gamma                100.289(4)
_cell_formula_units_Z            1
_cell_length_a                   9.0669(4)
_cell_length_b                   11.1569(4)
_cell_length_c                   12.8684(4)
_cell_measurement_reflns_used    3545
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.4580
_cell_measurement_theta_min      2.4250
_cell_volume                     1147.58(9)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0317
_diffrn_reflns_av_unetI/netI     0.0550
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8458
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.443
_exptl_absorpt_coefficient_mu    10.533
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5278
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
SADABS v.2.10 (Bruker,2003) was used for absorption correction.
R(int) for selected reflections was 0.1079 before and 0.0236 after
correction. The Ratio of minimum to maximum transmission is 0.42976.
The λ/2 correction factor is 0.0015
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.369
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             770
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.491
_refine_diff_density_min         -0.557
_refine_diff_density_rms         0.107
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         4508
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0543
_refine_ls_R_factor_gt           0.0347
_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/[σ²(Fo²)+(0.0164P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0564
_refine_ls_wR_factor_ref         0.0631
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3503
_reflns_number_total             4508
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4ra08452g2.cif
_cod_data_source_block           w1
_cod_original_cell_volume        1147.58(8)
_cod_database_code               7218145
#BEGIN Tags that were not found in dictionaries:
_shelxl_version_number           2013-2
_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.
;
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All O(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Riding coordinates:
 O6(H6), O3(H3), N1(H1), N2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C21(H21)
2.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C27(H27A,H27B,H27C)
;
_olex2_submission_special_instructions 'No special instructions were received'
#END Tags that were not found in dictionaries
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
Br3 Br 0.77649(6) 0.40714(5) 0.40692(4) 0.04242(14) Uani 1 1 d .
Br6 Br 0.40446(7) 0.21121(5) 0.30216(4) 0.04537(15) Uani 1 1 d .
O5 O 0.9240(4) 0.6499(4) 0.6784(2) 0.0566(10) Uani 1 1 d .
O6 O 0.8678(4) 0.7532(3) 0.5566(2) 0.0432(9) Uani 1 1 d .
H6 H 0.7928 0.7426 0.4982 0.052 Uiso 1 1 d R
C9 C 0.6571(5) 0.5809(4) 0.5462(3) 0.0266(10) Uani 1 1 d .
C14 C 0.4602(6) 0.3792(4) 0.4145(3) 0.0290(11) Uani 1 1 d .
C15 C 0.6167(5) 0.4596(4) 0.4597(3) 0.0276(10) Uani 1 1 d .
C26 C 0.8291(6) 0.6651(5) 0.6010(3) 0.0341(11) Uani 1 1 d .
Br4 Br 1.00544(7) 0.08616(5) -0.22175(3) 0.04382(15) Uani 1 1 d .
Br5 Br 1.26304(7) -0.06853(5) -0.11981(4) 0.04618(15) Uani 1 1 d .
O3 O 0.6485(4) 0.0655(3) -0.1637(2) 0.0411(9) Uani 1 1 d .
H3 H 0.5912 0.1103 -0.1831 0.049 Uiso 1 1 d R
O4 O 0.8197(4) 0.2591(3) -0.0431(2) 0.0401(8) Uani 1 1 d .
C6 C 0.8953(5) 0.0666(4) -0.0414(3) 0.0263(10) Uani 1 1 d .
C7 C 1.1113(5) -0.0288(4) -0.0518(3) 0.0286(10) Uani 1 1 d .
C10 C 0.7833(6) 0.1406(4) -0.0833(3) 0.0300(11) Uani 1 1 d .
C11 C 1.0039(5) 0.0360(4) -0.0941(3) 0.0284(11) Uani 1 1 d .
Br1 Br 0.83561(6) 0.07621(5) 0.45535(4) 0.04020(13) Uani 1 1 d .
Br2 Br 0.74781(6) 0.29038(4) 0.64981(3) 0.03799(13) Uani 1 1 d .
O1 O 0.5295(4) -0.1966(3) 0.22823(19) 0.0355(8) Uani 1 1 d .
O2 O 0.6466(4) -0.2674(3) 0.36465(19) 0.0352(8) Uani 1 1 d .
C2 C 0.6047(5) 0.1222(4) 0.5624(3) 0.0210(9) Uani 1 1 d .
C4 C 0.6432(5) 0.0320(4) 0.4826(3) 0.0213(9) Uani 1 1 d .
C8 C 0.5764(5) -0.1923(4) 0.3316(3) 0.0270(10) Uani 1 1 d .
C13 C 0.5370(5) -0.0908(4) 0.4194(3) 0.0199(9) Uani 1 1 d .
N1 N 0.5544(5) 0.4996(3) 0.1716(3) 0.0353(10) Uani 1 1 d .
H1 H 0.5704 0.5652 0.2324 0.042 Uiso 1 1 d R
N2 N 0.5972(5) 0.3625(4) 0.0404(3) 0.0421(11) Uani 1 1 d .
H2 H 0.6452 0.3217 -0.0006 0.050 Uiso 1 1 d R
C18 C 0.6686(6) 0.4675(4) 0.1346(3) 0.0365(12) Uani 1 1 d .
C20 C 0.4053(6) 0.4139(4) 0.0995(3) 0.0374(12) Uani 1 1 d .
C21 C 0.4355(7) 0.3278(4) 0.0175(4) 0.0431(13) Uani 1 1 d .
H21 H 0.3599 0.2569 -0.0442 0.052 Uiso 1 1 calc R
C24 C 0.8398(7) 0.5364(5) 0.1875(4) 0.0535(15) Uani 1 1 d .
H24A H 0.8597 0.6051 0.2591 0.080 Uiso 1 1 calc GR
H24B H 0.8724 0.5728 0.1357 0.080 Uiso 1 1 calc GR
H24C H 0.8996 0.4765 0.2026 0.080 Uiso 1 1 calc GR
C27 C 0.2528(7) 0.4259(5) 0.1162(4) 0.0575(16) Uani 1 1 d .
H27A H 0.2338 0.5051 0.1078 0.086 Uiso 1 1 calc GR
H27B H 0.2595 0.4274 0.1924 0.086 Uiso 1 1 calc GR
H27C H 0.1662 0.3529 0.0591 0.086 Uiso 1 1 calc GR
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 -0.2900 2.4600 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 '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
C26 O6 H6 109.4 . .
C14 C9 C15 119.5(4) 2_666 .
C14 C9 C26 120.4(4) 2_666 .
C15 C9 C26 120.0(4) . .
C9 C14 Br6 118.6(3) 2_666 .
C9 C14 C15 120.7(4) 2_666 .
C15 C14 Br6 120.6(3) . .
C9 C15 Br3 119.0(3) . .
C14 C15 Br3 121.2(3) . .
C14 C15 C9 119.8(4) . .
O5 C26 O6 122.4(4) . .
O5 C26 C9 121.4(4) . .
O6 C26 C9 116.1(4) . .
C10 O3 H3 109.4 . .
C7 C6 C10 119.0(4) 2_755 .
C11 C6 C7 120.3(4) . 2_755
C11 C6 C10 120.8(4) . .
C6 C7 Br5 119.4(3) 2_755 .
C6 C7 C11 119.4(4) 2_755 .
C11 C7 Br5 121.2(3) . .
O3 C10 C6 113.1(4) . .
O4 C10 O3 125.5(4) . .
O4 C10 C6 121.4(4) . .
C6 C11 Br4 118.7(3) . .
C6 C11 C7 120.3(4) . .
C7 C11 Br4 121.0(3) . .
C4 C2 Br2 120.6(3) . .
C13 C2 Br2 118.5(3) 2_656 .
C13 C2 C4 120.9(4) 2_656 .
C2 C4 Br1 120.9(3) . .
C13 C4 Br1 119.3(3) . .
C13 C4 C2 119.8(4) . .
O1 C8 C13 117.1(3) . .
O2 C8 O1 124.1(3) . .
O2 C8 C13 118.7(3) . .
C2 C13 C4 119.3(3) 2_656 .
C2 C13 C8 119.7(4) 2_656 .
C4 C13 C8 121.0(4) . .
C18 N1 H1 124.4 . .
C18 N1 C20 111.1(3) . .
C20 N1 H1 124.4 . .
C18 N2 H2 125.0 . .
C18 N2 C21 110.0(4) . .
C21 N2 H2 125.0 . .
N1 C18 C24 126.5(4) . .
N2 C18 N1 106.3(4) . .
N2 C18 C24 127.2(5) . .
N1 C20 C27 124.1(4) . .
C21 C20 N1 104.6(5) . .
C21 C20 C27 131.3(5) . .
N2 C21 H21 126.0 . .
C20 C21 N2 107.9(4) . .
C20 C21 H21 126.0 . .
C18 C24 H24A 109.5 . .
C18 C24 H24B 109.5 . .
C18 C24 H24C 109.5 . .
H24A C24 H24B 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
C20 C27 H27A 109.5 . .
C20 C27 H27B 109.5 . .
C20 C27 H27C 109.5 . .
H27A C27 H27B 109.5 . .
H27A C27 H27C 109.5 . .
H27B C27 H27C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br3 C15 1.881(4) .
Br6 C14 1.887(4) .
O5 C26 1.193(5) .
O6 H6 0.8199 .
O6 C26 1.313(5) .
C9 C14 1.391(6) 2_666
C9 C15 1.392(5) .
C9 C26 1.512(6) .
C14 C9 1.391(6) 2_666
C14 C15 1.391(6) .
Br4 C11 1.884(4) .
Br5 C7 1.880(4) .
O3 H3 0.8201 .
O3 C10 1.299(5) .
O4 C10 1.217(5) .
C6 C7 1.392(5) 2_755
C6 C10 1.499(5) .
C6 C11 1.384(6) .
C7 C6 1.392(5) 2_755
C7 C11 1.393(6) .
Br1 C4 1.884(4) .
Br2 C2 1.889(4) .
O1 C8 1.260(4) .
O2 C8 1.236(4) .
C2 C4 1.390(5) .
C2 C13 1.373(6) 2_656
C4 C13 1.383(5) .
C8 C13 1.527(5) .
C13 C2 1.373(6) 2_656
N1 H1 0.8600 .
N1 C18 1.320(6) .
N1 C20 1.387(6) .
N2 H2 0.8600 .
N2 C18 1.317(5) .
N2 C21 1.369(6) .
C18 C24 1.462(7) .
C20 C21 1.339(6) .
C20 C27 1.481(7) .
C21 H21 0.9300 .
C24 H24A 0.9600 .
C24 H24B 0.9600 .
C24 H24C 0.9600 .
C27 H27A 0.9600 .
C27 H27B 0.9600 .
C27 H27C 0.9600 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139199202
