#------------------------------------------------------------------------------
#$Date: 2020-09-30 03:27:55 +0200 (Wed 30 de Sep de 2020) $
#$Revision: 256843 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/13/7241324.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_7241324
loop_
_publ_author_name
'Singha, Soumen'
'Goswami, Somen'
'Dey, Sanjoy Kumar'
'Jana, Rajkumar'
'Ray, Partha Pratim'
'Saha, Indrajit'
'Rizzoli, Corrado'
'Bag, Partha Pratim'
'Kumar, Sanjay'
'SAHA, RAJAT'
_publ_section_title
;
 Synergistic Effect of Various Intermolecular Interactions on
 Self-assembly and Optoelectronic Behaviour in Co-crystals/Salts of
 Tetrabromoterephthalic Acid: A Report on Their Structure, Theoretical
 Study and Hirshfeld Surface Analysis
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D0CE01102A
_journal_year                    2020
_chemical_formula_moiety         'C8 H2 Br4 O4, C5 H4 Br N'
_chemical_formula_sum            'C13 H6 Br5 N O4'
_chemical_formula_weight         639.74
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2018-05-06 deposited with the CCDC.	2020-09-29 downloaded from the CCDC.
;
_cell_angle_alpha                70.384(3)
_cell_angle_beta                 71.053(3)
_cell_angle_gamma                77.807(4)
_cell_formula_units_Z            2
_cell_length_a                   8.8412(19)
_cell_length_b                   9.012(2)
_cell_length_c                   12.227(3)
_cell_measurement_reflns_used    665
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      22.75
_cell_measurement_theta_min      7.40
_cell_volume                     862.2(3)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scan'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_av_unetI/netI     0.0609
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9209
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.496
_diffrn_reflns_theta_min         1.839
_exptl_absorpt_coefficient_mu    11.668
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.176
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.464
_exptl_crystal_description       block
_exptl_crystal_F_000             596
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.706
_refine_diff_density_min         -0.926
_refine_diff_density_rms         0.141
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.095
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3189
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0407
_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)+(0.0574P)²+0.3159P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1179
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2649
_reflns_number_total             3189
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ce01102a2.cif
_cod_data_source_block           SK14
_cod_database_code               7241324
_shelx_shelxl_version_number     2014/7
_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.
;
_shelx_estimated_absorpt_t_min   0.174
_shelx_estimated_absorpt_t_max   0.292
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
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.58513(7) 0.27146(6) 0.58763(4) 0.04496(19) Uani 1 1 d . . . . .
Br2 Br 0.41866(7) 0.10398(6) 0.23856(4) 0.0493(2) Uani 1 1 d . . . . .
Br3 Br 0.32602(7) 0.79236(7) 0.11632(6) 0.0531(2) Uani 1 1 d . . . . .
Br4 Br 0.10631(6) 0.55985(8) 0.08081(6) 0.0602(2) Uani 1 1 d . . . . .
Br5 Br 0.95756(10) 0.72948(14) 0.53736(8) 0.0967(3) Uani 1 1 d . . . . .
O1 O 0.4056(5) 0.4267(5) 0.3532(4) 0.0568(10) Uani 1 1 d . . . . .
O2 O 0.6629(5) 0.3461(4) 0.2759(3) 0.0533(10) Uani 1 1 d . . . . .
H2 H 0.6667 0.4392 0.2355 0.080 Uiso 1 1 calc R U . . .
O3 O 0.7186(4) 0.6294(4) 0.1496(3) 0.0415(8) Uani 1 1 d . . . . .
H3 H 0.7346 0.6994 0.1721 0.062 Uiso 1 1 calc R U . . .
O4 O 0.7372(5) 0.8122(4) -0.0290(3) 0.0499(10) Uani 1 1 d . . . . .
N1 N 0.8240(5) 0.8068(6) 0.2319(4) 0.0482(11) Uani 1 1 d . . . . .
C1 C 0.5086(6) 0.1557(6) 0.4254(4) 0.0345(10) Uani 1 1 d . . . . .
C2 C 0.5392(6) 0.1134(6) 0.5377(4) 0.0346(10) Uani 1 1 d . . . . .
C3 C 0.4687(6) 0.0430(6) 0.3884(4) 0.0350(11) Uani 1 1 d . . . . .
C4 C 0.5187(7) 0.3270(6) 0.3458(4) 0.0396(12) Uani 1 1 d . . . . .
C5 C 0.5917(6) 0.5930(6) 0.0202(4) 0.0327(10) Uani 1 1 d . . . . .
C6 C 0.4242(6) 0.6200(5) 0.0527(4) 0.0314(10) Uani 1 1 d . . . . .
C7 C 0.3344(6) 0.5277(6) 0.0339(4) 0.0341(10) Uani 1 1 d . . . . .
C8 C 0.6918(6) 0.6909(6) 0.0443(4) 0.0346(11) Uani 1 1 d . . . . .
C9 C 0.8523(7) 0.7416(8) 0.3400(6) 0.0531(14) Uani 1 1 d . . . . .
H9 H 0.8254 0.6402 0.3854 0.064 Uiso 1 1 calc R U . . .
C10 C 0.9209(7) 0.8241(9) 0.3840(6) 0.0619(17) Uani 1 1 d . . . . .
C11 C 0.9601(8) 0.9714(10) 0.3175(7) 0.082(2) Uani 1 1 d . . . . .
H11 H 1.0073 1.0279 0.3464 0.098 Uiso 1 1 calc R U . . .
C12 C 0.9291(9) 1.0376(9) 0.2054(7) 0.078(2) Uani 1 1 d . . . . .
H12 H 0.9558 1.1386 0.1585 0.094 Uiso 1 1 calc R U . . .
C13 C 0.8582(7) 0.9515(8) 0.1645(6) 0.0617(17) Uani 1 1 d . . . . .
H13 H 0.8348 0.9948 0.0905 0.074 Uiso 1 1 calc R U . . .
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'
Br Br -0.2901 2.4595 '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'
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
_geom_angle_publ_flag
C4 O2 H2 109.5 . . ?
C8 O3 H3 109.5 . . ?
C13 N1 C9 122.3(5) . . ?
C3 C1 C2 119.9(4) . . ?
C3 C1 C4 121.2(4) . . ?
C2 C1 C4 118.9(4) . . ?
C1 C2 C3 119.7(4) . 2_656 ?
C1 C2 Br1 118.7(4) . . ?
C3 C2 Br1 121.5(3) 2_656 . ?
C1 C3 C2 120.3(4) . 2_656 ?
C1 C3 Br2 119.5(3) . . ?
C2 C3 Br2 120.1(3) 2_656 . ?
O1 C4 O2 126.9(5) . . ?
O1 C4 C1 122.2(5) . . ?
O2 C4 C1 110.9(5) . . ?
C6 C5 C7 118.2(4) . 2_665 ?
C6 C5 C8 121.0(4) . . ?
C7 C5 C8 120.7(4) 2_665 . ?
C7 C6 C5 120.6(4) . . ?
C7 C6 Br3 121.5(4) . . ?
C5 C6 Br3 117.8(3) . . ?
C6 C7 C5 121.1(4) . 2_665 ?
C6 C7 Br4 121.2(4) . . ?
C5 C7 Br4 117.7(3) 2_665 . ?
O4 C8 O3 126.0(4) . . ?
O4 C8 C5 121.4(4) . . ?
O3 C8 C5 112.6(4) . . ?
N1 C9 C10 120.0(6) . . ?
N1 C9 H9 120.0 . . ?
C10 C9 H9 120.0 . . ?
C11 C10 C9 119.8(6) . . ?
C11 C10 Br5 121.2(5) . . ?
C9 C10 Br5 119.0(5) . . ?
C10 C11 C12 119.4(6) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C13 C12 C11 119.2(7) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
N1 C13 C12 119.3(7) . . ?
N1 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C2 1.886(5) . ?
Br2 C3 1.897(4) . ?
Br3 C6 1.890(5) . ?
Br4 C7 1.895(5) . ?
Br5 C10 1.885(6) . ?
O1 C4 1.197(7) . ?
O2 C4 1.293(6) . ?
O2 H2 0.8200 . ?
O3 C8 1.298(5) . ?
O3 H3 0.8200 . ?
O4 C8 1.206(6) . ?
N1 C13 1.324(8) . ?
N1 C9 1.336(7) . ?
C1 C3 1.388(6) . ?
C1 C2 1.397(6) . ?
C1 C4 1.526(7) . ?
C2 C3 1.398(6) 2_656 ?
C3 C2 1.398(6) 2_656 ?
C5 C6 1.393(7) . ?
C5 C7 1.396(7) 2_665 ?
C5 C8 1.525(6) . ?
C6 C7 1.380(6) . ?
C7 C5 1.396(7) 2_665 ?
C9 C10 1.372(8) . ?
C9 H9 0.9300 . ?
C10 C11 1.354(10) . ?
C11 C12 1.391(10) . ?
C11 H11 0.9300 . ?
C12 C13 1.384(9) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
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
_geom_hbond_site_symmetry_A
O2 H2 O3 0.82 1.75 2.557(5) 168 1_555
O3 H3 N1 0.82 1.81 2.598(4) 161 1_555
