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#$Date: 2025-08-22 18:52:37 +0300 (Fri, 22 Aug 2025) $
#$Revision: 301865 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/49/7224964.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_7224964
loop_
_publ_author_name
'Mavračić, Juraj'
'Cinčić, Dominik'
'Kaitner, Branko'
_publ_section_title
;
 Halogen bonding of N-bromosuccinimide by grinding
;
_journal_issue                   19
_journal_name_full               CrystEngComm
_journal_page_first              3343
_journal_paper_doi               10.1039/C6CE00638H
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety         'C10 H8 N2, 2(C4 H4 Br N O2)'
_chemical_formula_sum            'C18 H16 Br2 N4 O4'
_chemical_formula_weight         512.17
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2016-04-13 deposited with the CCDC.
2016-04-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 110.975(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   24.0130(10)
_cell_length_b                   4.8573(2)
_cell_length_c                   18.3684(7)
_cell_measurement_reflns_used    4867
_cell_measurement_temperature    295
_cell_measurement_theta_max      36
_cell_measurement_theta_min      4
_cell_volume                     2000.49(15)
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      295
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_device_type
;
Oxford Diffraction Xcalibur CCD
diffractometer
;
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0659
_diffrn_reflns_av_unetI/netI     0.1306
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            16541
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_min         4.210
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    4.084
_exptl_absorpt_correction_T_max  0.70498
_exptl_absorpt_correction_T_min  0.19176
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   'N.W. Alcock (1970). Cryst. Computing, p271'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_description       needle
_exptl_crystal_F_000             1016
_exptl_crystal_size_max          0.69
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.850
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.705
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     253
_refine_ls_number_reflns         4177
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.705
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0328
_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)+(0.0197P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0482
_refine_ls_wR_factor_ref         0.0522
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1958
_reflns_number_total             4177
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6ce00638h2.cif
_cod_data_source_block           shelx
_cod_depositor_comments
'Adding full bibliography for 7224964--7224965.cif.'
_cod_database_code               7224964
_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.
;
_shelxl_version_number           2013-4
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
C1 C 0.26275(18) 0.0285(7) 0.1555(2) 0.0523(9) Uani 1 1 d . .
C2 C 0.24537(16) -0.1775(7) 0.20421(19) 0.0678(11) Uani 1 1 d . .
H2A H 0.2233 -0.3282 0.1721 0.081 Uiso 1 1 calc R U
H2B H 0.2207 -0.0920 0.2296 0.081 Uiso 1 1 calc R U
C3 C 0.30292(16) -0.2808(7) 0.26402(19) 0.0661(11) Uani 1 1 d . .
H3A H 0.3056 -0.2300 0.3162 0.079 Uiso 1 1 calc R U
H3B H 0.3056 -0.4796 0.2613 0.079 Uiso 1 1 calc R U
C4 C 0.35163(18) -0.1443(7) 0.24355(18) 0.0501(9) Uani 1 1 d . .
C5 C 0.1438(2) 0.5433(7) -0.10119(18) 0.0533(10) Uani 1 1 d . .
C6 C 0.18820(15) 0.7000(7) -0.03483(17) 0.0588(10) Uani 1 1 d . .
H6A H 0.1863 0.6411 0.0147 0.071 Uiso 1 1 calc R U
H6B H 0.1803 0.8962 -0.0407 0.071 Uiso 1 1 calc R U
C7 C 0.24862(16) 0.6353(7) -0.03879(18) 0.0608(10) Uani 1 1 d . .
H7A H 0.2660 0.7984 -0.0525 0.073 Uiso 1 1 calc R U
H7B H 0.2755 0.5670 0.0110 0.073 Uiso 1 1 calc R U
C8 C 0.23744(18) 0.4180(7) -0.10087(19) 0.0513(9) Uani 1 1 d . .
C9 C 0.40966(15) 0.5628(7) 0.0056(2) 0.0560(10) Uani 1 1 d . .
H9 H 0.3787 0.4548 -0.0267 0.067 Uiso 1 1 calc R U
C10 C 0.43796(14) 0.7410(7) -0.02903(17) 0.0515(9) Uani 1 1 d . .
H10 H 0.4259 0.7499 -0.0831 0.062 Uiso 1 1 calc R U
C11 C 0.48422(13) 0.9055(6) 0.01720(17) 0.0396(8) Uani 1 1 d . .
C12 C 0.49917(15) 0.8757(7) 0.09681(19) 0.0562(10) Uani 1 1 d . .
H12 H 0.5300 0.9801 0.1308 0.067 Uiso 1 1 calc R U
C13 C 0.46871(16) 0.6925(7) 0.12638(19) 0.0585(10) Uani 1 1 d . .
H13 H 0.4800 0.6772 0.1802 0.070 Uiso 1 1 calc R U
C14 C 0.04272(17) -0.3033(7) -0.33042(18) 0.0600(10) Uani 1 1 d . .
H14 H 0.0363 -0.3289 -0.2839 0.072 Uiso 1 1 calc R U
C15 C 0.00945(14) -0.4561(7) -0.39441(18) 0.0535(10) Uani 1 1 d . .
H15 H -0.0183 -0.5829 -0.3903 0.064 Uiso 1 1 calc R U
C16 C 0.01741(14) -0.4204(6) -0.46423(15) 0.0384(8) Uani 1 1 d . .
C17 C 0.05865(14) -0.2270(7) -0.46601(17) 0.0530(9) Uani 1 1 d . .
H17 H 0.0649 -0.1920 -0.5123 0.064 Uiso 1 1 calc R U
C18 C 0.09068(15) -0.0853(7) -0.3993(2) 0.0578(10) Uani 1 1 d . .
H18 H 0.1188 0.0425 -0.4016 0.069 Uiso 1 1 calc R U
N1 N 0.32416(13) 0.0270(5) 0.17980(14) 0.0461(7) Uani 1 1 d . .
N2 N 0.17635(12) 0.3849(5) -0.13397(13) 0.0463(7) Uani 1 1 d . .
N3 N 0.42425(12) 0.5378(5) 0.08197(17) 0.0524(7) Uani 1 1 d . .
N4 N 0.08325(12) -0.1227(6) -0.33191(14) 0.0510(7) Uani 1 1 d . .
O1 O 0.23045(11) 0.1734(5) 0.10436(13) 0.0712(7) Uani 1 1 d . .
O2 O 0.40477(12) -0.1710(5) 0.27560(13) 0.0709(8) Uani 1 1 d . .
O3 O 0.08985(12) 0.5501(5) -0.12302(13) 0.0731(8) Uani 1 1 d . .
O4 O 0.27328(11) 0.2958(5) -0.12088(14) 0.0728(7) Uani 1 1 d . .
Br1 Br 0.36938(2) 0.25290(7) 0.13572(2) 0.05303(11) Uani 1 1 d . .
Br2 Br 0.13689(2) 0.14852(7) -0.22143(2) 0.05189(12) 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'
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_3
O1 C1 N1 124.7(3) .
O1 C1 C2 128.0(4) .
N1 C1 C2 107.3(3) .
C1 C2 C3 106.2(3) .
C4 C3 C2 105.2(3) .
O2 C4 N1 125.0(3) .
O2 C4 C3 127.7(3) .
N1 C4 C3 107.2(3) .
O3 C5 N2 125.2(3) .
O3 C5 C6 128.1(3) .
N2 C5 C6 106.7(3) .
C5 C6 C7 105.7(3) .
C8 C7 C6 105.6(3) .
O4 C8 N2 124.7(3) .
O4 C8 C7 128.5(3) .
N2 C8 C7 106.8(3) .
N3 C9 C10 123.7(3) .
C11 C10 C9 119.7(3) .
C12 C11 C10 115.8(3) .
C12 C11 C11 122.8(4) 3_675
C10 C11 C11 121.4(3) 3_675
C13 C12 C11 120.7(3) .
N3 C13 C12 123.3(3) .
N4 C14 C15 123.2(3) .
C16 C15 C14 119.8(3) .
C15 C16 C17 116.8(3) .
C15 C16 C16 122.3(4) 3_544
C17 C16 C16 120.9(4) 3_544
C16 C17 C18 119.9(3) .
N4 C18 C17 123.0(3) .
C1 N1 C4 113.8(3) .
C1 N1 Br1 124.2(2) .
C4 N1 Br1 121.8(2) .
C5 N2 C8 114.9(3) .
C5 N2 Br2 120.7(2) .
C8 N2 Br2 124.4(2) .
C13 N3 C9 116.8(3) .
C14 N4 C18 117.3(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 O1 1.208(4) .
C1 N1 1.379(4) .
C1 C2 1.497(4) .
C2 C3 1.511(4) .
C3 C4 1.505(4) .
C4 O2 1.206(4) .
C4 N1 1.395(4) .
C5 O3 1.211(4) .
C5 N2 1.380(4) .
C5 C6 1.508(4) .
C6 C7 1.511(4) .
C7 C8 1.506(4) .
C8 O4 1.206(4) .
C8 N2 1.382(4) .
C9 N3 1.324(4) .
C9 C10 1.387(4) .
C10 C11 1.385(4) .
C11 C12 1.383(4) .
C11 C11 1.470(5) 3_675
C12 C13 1.380(4) .
C13 N3 1.321(4) .
C14 N4 1.318(4) .
C14 C15 1.378(4) .
C15 C16 1.373(4) .
C16 C17 1.374(4) .
C16 C16 1.496(5) 3_544
C17 C18 1.376(4) .
C18 N4 1.324(4) .
N1 Br1 1.915(3) .
N2 Br2 1.925(2) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139201988
