#------------------------------------------------------------------------------
#$Date: 2025-08-21 23:04:39 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301851 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/05/64/7056447.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_7056447
loop_
_publ_author_name
'Wang, Jin-Wen'
'Chen, Chen'
'Li, Yao-Jia'
'Luo, Yang-Hui'
'Sun, Baiwang'
_publ_section_title
;
 Halogen-bonding contacts determining the crystal structure and
 fluorescence properties of organic salts
;
_journal_issue                   17
_journal_name_full               'New J. Chem.'
_journal_page_first              9444
_journal_page_last               9452
_journal_paper_doi               10.1039/C7NJ02034A
_journal_volume                  41
_journal_year                    2017
_chemical_formula_sum            'C9 H7 Br N4'
_chemical_formula_weight         251.10
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_audit_update_record
;
2017-06-29 deposited with the CCDC.
2017-07-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.49(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   4.2810(9)
_cell_length_b                   11.572(2)
_cell_length_c                   19.146(4)
_cell_measurement_temperature    293(2)
_cell_volume                     946.7(3)
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.0890
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.362
_diffrn_reflns_theta_min         2.057
_exptl_absorpt_coefficient_mu    4.304
_exptl_crystal_density_diffrn    1.762
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.622
_refine_diff_density_rms         0.098
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1733
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.1221
_refine_ls_R_factor_gt           0.0546
_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)+(0.0350P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0903
_refine_ls_wR_factor_ref         0.1055
_reflns_Friedel_coverage         0.000
_reflns_number_gt                953
_reflns_number_total             1733
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7nj02034a2.cif
_cod_data_source_block           X_CCDC1
_cod_database_code               7056447
#BEGIN Tags that were not found in dictionaries:
_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   0.480
_shelx_estimated_absorpt_t_max   0.673
_shelxl_version_number           2014-3
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
Br Br 0.16378(17) 0.62763(6) 0.59002(4) 0.0595(3) Uani 1 1 d . .
N1 N 1.4045(14) 1.0295(6) 0.2179(3) 0.0698(18) Uani 1 1 d . .
C1 C 1.2567(16) 0.9529(7) 0.2527(3) 0.060(2) Uani 1 1 d . .
H1B H 1.2480 0.8744 0.2421 0.072 Uiso 1 1 calc R U
N2 N 1.3637(13) 1.1356(6) 0.2498(3) 0.0660(16) Uani 1 1 d . .
C2 C 1.1957(16) 1.1159(6) 0.3028(3) 0.0620(19) Uani 1 1 d . .
H2B H 1.1379 1.1724 0.3341 0.074 Uiso 1 1 calc R U
C3 C 0.8748(14) 0.8545(6) 0.3591(3) 0.0483(17) Uani 1 1 d . .
H3A H 0.9427 0.8084 0.3232 0.058 Uiso 1 1 calc R U
N3 N 1.1153(11) 1.0033(4) 0.3070(3) 0.0463(14) Uani 1 1 d . .
N4 N 0.9424(12) 0.9614(4) 0.3606(2) 0.0487(14) Uani 1 1 d . .
C4 C 0.6922(14) 0.8033(5) 0.4128(3) 0.0445(16) Uani 1 1 d . .
C5 C 0.6354(13) 0.8639(5) 0.4740(3) 0.0479(16) Uani 1 1 d . .
H5A H 0.7115 0.9387 0.4803 0.057 Uiso 1 1 calc R U
C6 C 0.4696(14) 0.8143(6) 0.5244(3) 0.0494(17) Uani 1 1 d . .
H6A H 0.4276 0.8561 0.5643 0.059 Uiso 1 1 calc R U
C7 C 0.3624(15) 0.7013(5) 0.5167(3) 0.0472(17) Uani 1 1 d . .
C8 C 0.4176(14) 0.6401(6) 0.4564(3) 0.0532(17) Uani 1 1 d . .
H8A H 0.3442 0.5649 0.4507 0.064 Uiso 1 1 calc R U
C9 C 0.5817(15) 0.6916(6) 0.4053(3) 0.0529(18) Uani 1 1 d . .
H9A H 0.6190 0.6504 0.3650 0.063 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'
N N 0.0061 0.0033 '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
C1 N1 N2 107.5(6)
N1 C1 N3 110.6(6)
N1 C1 H1B 124.7
N3 C1 H1B 124.7
C2 N2 N1 106.2(6)
N2 C2 N3 111.8(7)
N2 C2 H2B 124.1
N3 C2 H2B 124.1
N4 C3 C4 120.8(5)
N4 C3 H3A 119.6
C4 C3 H3A 119.6
C2 N3 C1 103.9(5)
C2 N3 N4 122.0(5)
C1 N3 N4 133.9(6)
C3 N4 N3 117.1(5)
C9 C4 C5 118.7(6)
C9 C4 C3 120.2(6)
C5 C4 C3 121.1(6)
C6 C5 C4 120.5(6)
C6 C5 H5A 119.8
C4 C5 H5A 119.8
C5 C6 C7 120.3(6)
C5 C6 H6A 119.8
C7 C6 H6A 119.8
C8 C7 C6 119.8(6)
C8 C7 Br 119.7(5)
C6 C7 Br 120.4(5)
C9 C8 C7 119.4(6)
C9 C8 H8A 120.3
C7 C8 H8A 120.3
C8 C9 C4 121.2(6)
C8 C9 H9A 119.4
C4 C9 H9A 119.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br C7 1.889(6)
N1 C1 1.296(8)
N1 N2 1.387(8)
C1 N3 1.365(7)
C1 H1B 0.9300
N2 C2 1.299(8)
C2 N3 1.351(7)
C2 H2B 0.9300
C3 N4 1.270(7)
C3 C4 1.455(8)
C3 H3A 0.9300
N3 N4 1.389(6)
C4 C9 1.381(8)
C4 C5 1.400(8)
C5 C6 1.359(8)
C5 H5A 0.9300
C6 C7 1.390(8)
C6 H6A 0.9300
C7 C8 1.385(8)
C8 C9 1.375(8)
C8 H8A 0.9300
C9 H9A 0.9300
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
N2 N1 C1 N3 0.3(8)
C1 N1 N2 C2 0.8(8)
N1 N2 C2 N3 -1.7(8)
N2 C2 N3 C1 1.8(8)
N2 C2 N3 N4 178.3(5)
N1 C1 N3 C2 -1.2(8)
N1 C1 N3 N4 -177.1(6)
C4 C3 N4 N3 -179.5(5)
C2 N3 N4 C3 178.9(6)
C1 N3 N4 C3 -5.8(10)
N4 C3 C4 C9 170.6(6)
N4 C3 C4 C5 -11.9(10)
C9 C4 C5 C6 -1.2(9)
C3 C4 C5 C6 -178.7(6)
C4 C5 C6 C7 1.9(10)
C5 C6 C7 C8 -1.7(10)
C5 C6 C7 Br 174.5(5)
C6 C7 C8 C9 0.8(10)
Br C7 C8 C9 -175.4(5)
C7 C8 C9 C4 -0.1(10)
C5 C4 C9 C8 0.3(10)
C3 C4 C9 C8 177.8(6)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 6858416
