Two-dimensional halogen-bonded organic frameworks based on the tetrabromobenzene-1,4-dicarboxylic acid building molecule
Chongboriboon, Nucharee; Samakun, Kodchakorn; Inprasit, Thitirat; Kielar, Filip; Dungkaew, Winya; Wong, Lawrence W.-Y.; Sung, Herman H.-Y.; Ninković, Dragan B.; Zarić, Snežana D.; Chainok, Kittipong; CrystEngComm 22 (2020) 24–34; doi:10.1039/C9CE01140D

data_7234791
_publ_section_title
;
 Two-dimensional halogen-bonded organic frameworks based on the
 tetrabromobenzene-1,4-dicarboxylic acid building molecule
;
_journal_issue                   1
_journal_name_full               CrystEngComm
_journal_page_first              24
_journal_page_last               34
_journal_paper_doi               10.1039/C9CE01140D
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         'C8 H2 Br4 O4, 2(C3 H6 O)'
_chemical_formula_sum            'C14 H14 Br4 O6'
_chemical_formula_weight         597.89
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2019-07-18
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-07-18 deposited with the CCDC.    2019-10-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.248(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.9223(4)
_cell_length_b                   9.0196(2)
_cell_length_c                   8.88690(10)
_cell_measurement_reflns_used    3867
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      73.4930
_cell_measurement_theta_min      5.2040
_cell_volume                     1994.47(6)
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3577
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     82.00 134.00   1.00   15.00    --  106.99 -61.00 -30.00   52
  2  \w   -115.00 -22.00   1.00    5.00    --  -40.57 -57.00-180.00   93
  3  \w    -92.00 -11.00   1.00    5.00    --  -40.57 125.00 -60.00   81
  4  \w   -115.00 -15.00   1.00    5.00    --  -40.57 -37.00  60.00  100
  5  \w     -7.00  22.00   1.00    5.00    --   40.57 -84.00 -62.00   29
  6  \w     52.00 110.00   1.00   15.00    --  106.99 -94.00 120.00   58
  7  \w     36.00  79.00   1.00   15.00    --  106.99 -61.00 -30.00   43
  8  \w     98.00 175.00   1.00   15.00    --  106.99  84.00  57.00   77
  9  \w     41.00 110.00   1.00   15.00    --  106.99 -94.00 -30.00   69
 10  \w    107.00 178.00   1.00   15.00    --  106.99 125.00   0.00   71
 11  \w     32.00 122.00   1.00   15.00    --  106.99 -45.00  90.00   90
 12  \w     23.00  49.00   1.00   15.00    --  106.99 -94.00 120.00   26
 13  \w     24.00 165.00   1.00   15.00    --  106.99 -15.00-120.00  141
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0674271000
_diffrn_orient_matrix_UB_12      0.0326536000
_diffrn_orient_matrix_UB_13      -0.0544194000
_diffrn_orient_matrix_UB_21      -0.0580937000
_diffrn_orient_matrix_UB_22      0.1607382000
_diffrn_orient_matrix_UB_23      0.0023542000
_diffrn_orient_matrix_UB_31      0.1488815000
_diffrn_orient_matrix_UB_32      0.0479263000
_diffrn_orient_matrix_UB_33      0.0294883000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            5459
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.805
_diffrn_reflns_theta_min         3.553
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    10.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.79633
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.991
_exptl_crystal_description       block
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.370
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.000117(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     155
_refine_ls_number_reflns         1977
_refine_ls_number_restraints     44
_refine_ls_restrained_S_all      1.094
_refine_ls_R_factor_all          0.0182
_refine_ls_R_factor_gt           0.0166
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0243P)^2^+0.5237P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0428
_refine_ls_wR_factor_ref         0.0437
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1856
_reflns_number_total             1977
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ce01140d2.cif
_cod_data_source_block           1atn_lt
_cod_depositor_comments
;Adding full bibliography for 7234791--7234798.cif.

 Adding full bibliography for 7234791--7234798.cif.
;
_cod_database_code               7234791
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.196
_shelx_estimated_absorpt_t_min   0.179
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O1-H1
 0.84 with sigma of 0.02
 C7A-C5A \\sim C6A-C5A
 with sigma of 0.02
 C6B-C5B \\sim C7B-C5B
 with sigma of 0.02
 C6A-O3A \\sim O3A-C7A
 with sigma of 0.02
 O3B-C6B \\sim C6B-C7B
 with sigma of 0.02
 O3A-C5A \\sim O3B-C5B
 with sigma of 0.02
 C7A-C6A \\sim C6B-C7B
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 O3A, C5A, C6A, C7A
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
 O3B, C5B, C6B, C7B
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
4. Others
 Sof(O3B)=Sof(C5B)=Sof(C6B)=Sof(H6BA)=Sof(H6BB)=Sof(H6BC)=Sof(C7B)=Sof(H7BA)=
 Sof(H7BB)=Sof(H7BC)=1-FVAR(1)
 Sof(O3A)=Sof(C5A)=Sof(C6A)=Sof(H6AA)=Sof(H6AB)=Sof(H6AC)=Sof(C7A)=Sof(H7AA)=
 Sof(H7AB)=Sof(H7AC)=FVAR(1)
5.a Idealised Me refined as rotating group:
 C6A(H6AA,H6AB,H6AC), C6B(H6BA,H6BB,H6BC), C7A(H7AA,H7AB,H7AC), C7B(H7BA,H7BB,
 H7BC)
;
_shelx_res_checksum              65518
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.180
_oxdiff_exptl_absorpt_empirical_full_min 0.820