#------------------------------------------------------------------------------
#$Date: 2016-03-26 22:36:24 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180512 $
#$URL: svn://www.crystallography.net/cod/cif/7/21/81/7218147.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_7218147
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         'C8 H2 Br4 O4, C20 H10 Br4 N4 O4'
_chemical_formula_sum            'C28 H10 Br8 N4 O8'
_chemical_formula_weight         1169.60
_chemical_name_systematic
;
 ?
;
_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                105.180(7)
_cell_angle_beta                 109.306(6)
_cell_angle_gamma                96.573(6)
_cell_formula_units_Z            1
_cell_length_a                   8.8990(5)
_cell_length_b                   9.0236(7)
_cell_length_c                   12.0472(8)
_cell_measurement_reflns_used    2200
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.2140
_cell_measurement_theta_min      2.5750
_cell_volume                     859.41(12)
_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 0.999
_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  0.0419
_diffrn_reflns_av_unetI/netI     0.0806
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6165
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.499
_diffrn_reflns_theta_min         2.486
_exptl_absorpt_coefficient_mu    9.386
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.5284
_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    2.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             550
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         2.085
_refine_diff_density_min         -1.939
_refine_diff_density_rms         0.280
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3556
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0868
_refine_ls_R_factor_gt           0.0580
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 w=1/[σ²(Fo²)+(0.0841P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1419
_refine_ls_wR_factor_ref         0.1581
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2594
_reflns_number_total             3556
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c4ra08452g2.cif
_cod_data_source_block           w1
_cod_original_cell_volume        859.41(11)
_cod_database_code               7218147
#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
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C21(H21), C30(H30), C31(H31), C32(H32)
2.b Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_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
Br2 Br 0.83775(10) 0.78289(10) -0.07903(7) 0.0331(3) Uani 1 1 d .
Br4 Br 0.66426(10) 0.40755(11) -0.24702(7) 0.0333(3) Uani 1 1 d .
O3 O 1.2426(8) 0.9103(7) 0.1330(6) 0.0451(17) Uani 1 1 d .
O4 O 1.0780(7) 0.8676(7) 0.2322(5) 0.0361(15) Uani 1 1 d .
H4 H 1.1236 0.9577 0.2782 0.054 Uiso 1 1 calc GR
C7 C 0.8579(8) 0.4631(9) -0.1046(6) 0.0200(16) Uani 1 1 d .
C9 C 0.9283(9) 0.6194(9) -0.0331(6) 0.0188(15) Uani 1 1 d .
C12 C 1.0690(9) 0.6548(10) 0.0711(6) 0.0247(18) Uani 1 1 d .
C24 C 1.1439(10) 0.8269(10) 0.1499(7) 0.0267(18) Uani 1 1 d .
Br1 Br 0.54928(10) 0.28414(10) 0.38520(8) 0.0328(3) Uani 1 1 d .
Br3 Br 0.80609(9) 0.04071(11) 0.41055(8) 0.0331(3) Uani 1 1 d .
O1 O 0.1442(6) 0.1503(7) 0.3717(5) 0.0282(13) Uani 1 1 d .
O2 O 0.3016(6) 0.3351(7) 0.5509(5) 0.0321(14) Uani 1 1 d .
C3 C 0.3920(8) 0.1019(8) 0.4888(6) 0.0161(15) Uani 1 1 d .
C5 C 0.6276(8) 0.0186(9) 0.4613(6) 0.0181(15) Uani 1 1 d .
C6 C 0.5214(8) 0.1180(8) 0.4485(6) 0.0150(14) Uani 1 1 d .
C8 C 0.2738(8) 0.2096(9) 0.4727(6) 0.0155(15) Uani 1 1 d .
N1 N 0.9632(8) 0.3347(9) 0.2972(6) 0.0312(16) Uani 1 1 d .
N2 N 0.6138(11) 0.7043(13) 0.1042(8) 0.063(3) Uani 1 1 d .
C13 C 0.7821(10) 0.5235(12) 0.2011(8) 0.033(2) Uani 1 1 d .
C21 C 1.0102(10) 0.4888(11) 0.3531(7) 0.0313(19) Uani 1 1 d .
H21 H 1.1045 0.5301 0.4244 0.038 Uiso 1 1 calc R
C27 C 0.6850(12) 0.6207(13) 0.1455(9) 0.045(2) Uani 1 1 d .
C30 C 0.9212(10) 0.5870(11) 0.3068(7) 0.033(2) Uani 1 1 d .
H30 H 0.9538 0.6953 0.3460 0.039 Uiso 1 1 calc R
C31 C 0.8279(11) 0.2743(12) 0.1955(8) 0.042(2) Uani 1 1 d .
H31 H 0.7982 0.1657 0.1579 0.050 Uiso 1 1 calc R
C32 C 0.7315(10) 0.3636(12) 0.1443(8) 0.041(2) Uani 1 1 d .
H32 H 0.6360 0.3190 0.0743 0.050 Uiso 1 1 calc R
H1 H 1.064(10) 0.272(11) 0.342(7) 0.04(2) Uiso 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 0.0030 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
C24 O4 H4 109.5 . .
C9 C7 Br4 121.2(6) . .
C12 C7 Br4 119.2(5) 2_765 .
C12 C7 C9 119.6(7) 2_765 .
C7 C9 Br2 120.9(5) . .
C12 C9 Br2 119.8(6) . .
C12 C9 C7 119.3(7) . .
C7 C12 C24 120.1(7) 2_765 .
C9 C12 C7 121.1(7) . 2_765
C9 C12 C24 118.8(7) . .
O3 C24 O4 126.6(8) . .
O3 C24 C12 123.7(7) . .
O4 C24 C12 109.6(7) . .
C5 C3 C6 118.3(6) 2_656 .
C5 C3 C8 121.8(6) 2_656 .
C6 C3 C8 119.8(6) . .
C3 C5 Br3 117.5(5) 2_656 .
C6 C5 Br3 120.7(6) . .
C6 C5 C3 121.8(6) . 2_656
C3 C6 Br1 117.7(5) . .
C5 C6 Br1 122.2(5) . .
C5 C6 C3 119.9(7) . .
O1 C8 C3 113.4(6) . .
O2 C8 O1 126.0(7) . .
O2 C8 C3 120.6(6) . .
C21 N1 C31 120.3(8) . .
C21 N1 H1 110(4) . .
C31 N1 H1 129(4) . .
C30 C13 C27 121.8(9) . .
C32 C13 C27 117.4(8) . .
C32 C13 C30 120.9(8) . .
N1 C21 H21 119.8 . .
N1 C21 C30 120.3(8) . .
C30 C21 H21 119.8 . .
N2 C27 C13 176.7(13) . .
C13 C30 H30 120.5 . .
C21 C30 C13 118.9(9) . .
C21 C30 H30 120.5 . .
N1 C31 H31 118.5 . .
N1 C31 C32 123.1(10) . .
C32 C31 H31 118.5 . .
C13 C32 H32 121.8 . .
C31 C32 C13 116.5(8) . .
C31 C32 H32 121.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br2 C9 1.880(7) .
Br4 C7 1.887(7) .
O3 C24 1.194(10) .
O4 H4 0.8200 .
O4 C24 1.306(9) .
C7 C9 1.389(10) .
C7 C12 1.389(11) 2_765
C9 C12 1.381(10) .
C12 C7 1.389(11) 2_765
C12 C24 1.526(11) .
Br1 C6 1.879(7) .
Br3 C5 1.890(7) .
O1 C8 1.299(8) .
O2 C8 1.206(8) .
C3 C5 1.393(10) 2_656
C3 C6 1.396(10) .
C3 C8 1.512(9) .
C5 C3 1.393(10) 2_656
C5 C6 1.375(10) .
N1 C21 1.323(11) .
N1 C31 1.331(11) .
N1 H1 1.17(9) .
N2 C27 1.147(12) .
C13 C27 1.437(13) .
C13 C30 1.377(12) .
C13 C32 1.372(14) .
C21 H21 0.9300 .
C21 C30 1.361(12) .
C30 H30 0.9300 .
C31 H31 0.9300 .
C31 C32 1.355(13) .
C32 H32 0.9300 .
