#------------------------------------------------------------------------------
#$Date: 2025-08-19 00:15:59 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301787 $
#$URL: svn://www.crystallography.net/cod/cif/1/56/18/1561874.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_1561874
loop_
_publ_author_name
'John, Athira T.'
'Narayanasamy, Akshaya'
'George, Deepu'
'Hariharan, Mahesh'
_publ_section_title
;
 Atom-Efficient Halogen--Halogen Interactions Assist One-, Two-, and
 Three-Dimensional Molecular Zippers
;
_journal_name_full               'The Journal of Physical Chemistry C'
_journal_paper_doi               10.1021/acs.jpcc.1c01724
_journal_year                    2021
_chemical_formula_moiety         'C13 H9 Br2 N O S'
_chemical_formula_sum            'C13 H9 Br2 N O S'
_chemical_formula_weight         387.09
_chemical_name_systematic        NTB2
_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-2018/3
_cell_angle_alpha                104.639(13)
_cell_angle_beta                 91.864(13)
_cell_angle_gamma                95.118(14)
_cell_formula_units_Z            2
_cell_length_a                   4.0327(18)
_cell_length_b                   9.774(5)
_cell_length_c                   16.841(8)
_cell_measurement_reflns_used    1643
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      17.72
_cell_measurement_theta_min      2.20
_cell_volume                     638.6(5)
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_molecular_graphics    'ORTEP3- 2014.1(Farrugia, 1997) '
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker KAPPA APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1342
_diffrn_reflns_av_unetI/netI     0.0970
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16425
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.986
_diffrn_reflns_theta_max         24.986
_diffrn_reflns_theta_min         2.165
_diffrn_source                   'sealed tube'
_exptl_absorpt_coefficient_mu    6.495
_exptl_absorpt_correction_T_max  0.805
_exptl_absorpt_correction_T_min  0.463
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.013
_exptl_crystal_density_meas      2.014
_exptl_crystal_density_method    none
_exptl_crystal_description       needle
_exptl_crystal_F_000             376
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.045
_exptl_crystal_size_min          0.035
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.692
_refine_diff_density_rms         0.116
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2253
_refine_ls_number_restraints     74
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.1265
_refine_ls_R_factor_gt           0.0515
_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)+(0.0443P)²+1.9942P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1125
_refine_ls_wR_factor_ref         0.1477
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1222
_reflns_number_total             2253
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jp1c01724_si_002.cif
_cod_data_source_block           NTB2
_cod_database_code               1561874
_shelx_shelxl_version_number     2018/3
_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   0.463
_shelx_estimated_absorpt_t_max   0.805
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
C1 C 0.739(2) 0.2346(9) 0.6609(5) 0.046(2) Uani 1 1 d . U . . .
C2 C 0.760(2) 0.1464(10) 0.5819(5) 0.054(2) Uani 1 1 d . U . . .
H2 H 0.672033 0.051765 0.569261 0.065 Uiso 1 1 calc R U . . .
C3 C 0.911(2) 0.2001(11) 0.5238(6) 0.062(3) Uani 1 1 d . U . . .
H3 H 0.918304 0.141343 0.471148 0.074 Uiso 1 1 calc R U . . .
C4 C 1.053(2) 0.3393(11) 0.5402(6) 0.063(3) Uani 1 1 d . U . . .
H4 H 1.155697 0.372284 0.498973 0.076 Uiso 1 1 calc R U . . .
C5 C 1.042(2) 0.4283(11) 0.6170(5) 0.057(2) Uani 1 1 d . U . . .
H5 H 1.139074 0.521673 0.628646 0.068 Uiso 1 1 calc R U . . .
C6 C 0.883(2) 0.3770(10) 0.6778(5) 0.048(2) Uani 1 1 d . U . . .
C7 C 0.863(2) 0.4651(9) 0.7591(5) 0.044(2) Uani 1 1 d . U . . .
C8 C 0.707(2) 0.4097(9) 0.8175(5) 0.042(2) Uani 1 1 d . U . . .
C9 C 0.566(2) 0.2687(10) 0.8000(5) 0.045(2) Uani 1 1 d . U . . .
C10 C 0.580(2) 0.1806(10) 0.7230(5) 0.045(2) Uani 1 1 d . U . . .
C11 C 0.641(3) -0.0549(11) 0.7232(7) 0.083(4) Uani 1 1 d D U . . .
H11A H 0.868491 -0.033489 0.709404 0.099 Uiso 1 1 calc R U . . .
H11B H 0.642348 -0.045747 0.781947 0.099 Uiso 1 1 calc R U . . .
C12 C 0.523(5) -0.1966(16) 0.6801(11) 0.182(8) Uani 1 1 d D U . . .
H12A H 0.664681 -0.261317 0.694863 0.273 Uiso 1 1 calc R U . . .
H12B H 0.299498 -0.218232 0.694454 0.273 Uiso 1 1 calc R U . . .
H12C H 0.525279 -0.205994 0.622028 0.273 Uiso 1 1 calc R U . . .
C13 C 0.933(2) 0.6553(10) 0.8618(6) 0.052(2) Uani 1 1 d . . . . .
N1 N 0.9913(18) 0.6069(8) 0.7860(4) 0.0490(19) Uani 1 1 d . . . . .
O1 O 0.4348(15) 0.0441(6) 0.7025(4) 0.0563(17) Uani 1 1 d . . . . .
S1 S 0.7186(6) 0.5381(3) 0.90980(14) 0.0527(6) Uani 1 1 d . . . . .
Br1 Br 0.3569(3) 0.20359(11) 0.88424(6) 0.0614(4) Uani 1 1 d . . . . .
Br2 Br 1.0669(3) 0.83966(11) 0.92116(6) 0.0695(4) Uani 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 0.0033 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'
S S 0.1246 0.1234 '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
_geom_angle_publ_flag
C2 C1 C6 118.2(9) . . ?
C2 C1 C10 120.6(9) . . ?
C6 C1 C10 121.2(8) . . ?
C3 C2 C1 119.6(9) . . ?
C2 C3 C4 122.3(9) . . ?
C5 C4 C3 119.9(9) . . ?
C4 C5 C6 119.1(10) . . ?
C5 C6 C1 120.8(8) . . ?
C5 C6 C7 121.6(9) . . ?
C1 C6 C7 117.6(8) . . ?
C8 C7 N1 115.2(7) . . ?
C8 C7 C6 119.7(8) . . ?
N1 C7 C6 125.1(8) . . ?
C7 C8 C9 122.0(8) . . ?
C7 C8 S1 110.2(6) . . ?
C9 C8 S1 127.8(7) . . ?
C10 C9 C8 120.1(8) . . ?
C10 C9 Br1 121.2(7) . . ?
C8 C9 Br1 118.7(6) . . ?
O1 C10 C9 121.9(8) . . ?
O1 C10 C1 118.6(8) . . ?
C9 C10 C1 119.4(8) . . ?
C12 C11 O1 110.7(11) . . ?
N1 C13 S1 117.1(7) . . ?
N1 C13 Br2 123.3(7) . . ?
S1 C13 Br2 119.6(5) . . ?
C13 N1 C7 109.7(8) . . ?
C10 O1 C11 113.5(7) . . ?
C8 S1 C13 87.8(4) . . ?
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
C1 C2 1.401(11) . ?
C1 C6 1.416(12) . ?
C1 C10 1.428(12) . ?
C2 C3 1.356(13) . ?
C3 C4 1.384(13) . ?
C4 C5 1.370(12) . ?
C5 C6 1.397(12) . ?
C6 C7 1.430(11) . ?
C7 C8 1.381(11) . ?
C7 N1 1.390(10) . ?
C8 C9 1.398(11) . ?
C8 S1 1.729(8) . ?
C9 C10 1.370(11) . ?
C9 Br1 1.889(8) . ?
C10 O1 1.364(10) . ?
C11 C12 1.423(13) . ?
C11 O1 1.431(11) . ?
C13 N1 1.282(10) . ?
C13 S1 1.746(10) . ?
C13 Br2 1.849(9) . ?
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
_geom_hbond_publ_flag
C11 H11B Br1 0.97 2.96 3.508(11) 117.3 . yes
C12 H12A N1 0.96 2.63 3.55(2) 160.0 1_545 yes
C11 H11B Br1 0.97 2.96 3.508(11) 117.3 . yes
C12 H12A N1 0.96 2.63 3.55(2) 160.0 1_545 yes
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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -1.4(13) . . . . ?
C10 C1 C2 C3 179.7(9) . . . . ?
C1 C2 C3 C4 1.6(15) . . . . ?
C2 C3 C4 C5 -0.6(15) . . . . ?
C3 C4 C5 C6 -0.6(15) . . . . ?
C4 C5 C6 C1 0.8(14) . . . . ?
C4 C5 C6 C7 -179.8(8) . . . . ?
C2 C1 C6 C5 0.3(13) . . . . ?
C10 C1 C6 C5 179.1(8) . . . . ?
C2 C1 C6 C7 -179.2(8) . . . . ?
C10 C1 C6 C7 -0.4(12) . . . . ?
C5 C6 C7 C8 -179.4(8) . . . . ?
C1 C6 C7 C8 0.0(12) . . . . ?
C5 C6 C7 N1 0.6(14) . . . . ?
C1 C6 C7 N1 -179.9(8) . . . . ?
N1 C7 C8 C9 -179.8(8) . . . . ?
C6 C7 C8 C9 0.2(13) . . . . ?
N1 C7 C8 S1 -0.1(10) . . . . ?
C6 C7 C8 S1 179.9(6) . . . . ?
C7 C8 C9 C10 -0.1(13) . . . . ?
S1 C8 C9 C10 -179.7(7) . . . . ?
C7 C8 C9 Br1 -179.9(6) . . . . ?
S1 C8 C9 Br1 0.4(11) . . . . ?
C8 C9 C10 O1 -177.3(8) . . . . ?
Br1 C9 C10 O1 2.5(12) . . . . ?
C8 C9 C10 C1 -0.3(13) . . . . ?
Br1 C9 C10 C1 179.5(6) . . . . ?
C2 C1 C10 O1 -3.5(13) . . . . ?
C6 C1 C10 O1 177.7(7) . . . . ?
C2 C1 C10 C9 179.3(8) . . . . ?
C6 C1 C10 C9 0.5(13) . . . . ?
S1 C13 N1 C7 -0.1(10) . . . . ?
Br2 C13 N1 C7 179.3(6) . . . . ?
C8 C7 N1 C13 0.1(11) . . . . ?
C6 C7 N1 C13 -179.9(8) . . . . ?
C9 C10 O1 C11 -85.3(11) . . . . ?
C1 C10 O1 C11 97.6(10) . . . . ?
C12 C11 O1 C10 -163.0(12) . . . . ?
C7 C8 S1 C13 0.1(7) . . . . ?
C9 C8 S1 C13 179.8(8) . . . . ?
N1 C13 S1 C8 0.0(8) . . . . ?
Br2 C13 S1 C8 -179.4(6) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 168307408
