#------------------------------------------------------------------------------
#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/14/7231470.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_7231470
loop_
_publ_author_name
'Hutchins, Kristin M.'
'Unruh, Daniel K.'
'Carpenter, Dontrell D.'
'Groeneman, Ryan H.'
_publ_section_title
;
 Thermal expansion along one-dimensional chains and two-dimensional sheets
 within co-crystals based on halogen or hydrogen bonds
;
_journal_issue                   45
_journal_name_full               CrystEngComm
_journal_page_first              7232
_journal_paper_doi               10.1039/C8CE01090K
_journal_volume                  20
_journal_year                    2018
_chemical_formula_sum            'C18 H10 Br4 N2'
_chemical_formula_weight         573.92
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-04-23T11:20:51-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2018-06-18 deposited with the CCDC.
2018-08-30 downloaded from the CCDC.
;
_cell_angle_alpha                72.838(2)
_cell_angle_beta                 85.776(2)
_cell_angle_gamma                83.982(2)
_cell_formula_units_Z            2
_cell_length_a                   3.9472(3)
_cell_length_b                   13.2528(10)
_cell_length_c                   18.2138(15)
_cell_measurement_reflns_used    4203
_cell_measurement_temperature    229(2)
_cell_measurement_theta_max      27.99
_cell_measurement_theta_min      2.25
_cell_volume                     904.43(12)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      229(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0890
_diffrn_reflns_av_unetI/netI     0.0787
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            10322
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.326
_diffrn_reflns_theta_min         1.614
_exptl_absorpt_coefficient_mu    8.901
_exptl_absorpt_correction_T_max  0.1256
_exptl_absorpt_correction_T_min  0.0679
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.107
_exptl_crystal_description       rod
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.498
_exptl_crystal_size_mid          0.221
_exptl_crystal_size_min          0.092
_refine_diff_density_max         1.309
_refine_diff_density_min         -2.168
_refine_diff_density_rms         0.222
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.966
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         4483
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.966
_refine_ls_R_factor_all          0.0701
_refine_ls_R_factor_gt           0.053
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0735P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1277
_refine_ls_wR_factor_ref         0.1329
_reflns_number_gt                3203
_reflns_number_total             4483
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce01090k2.cif
_cod_data_source_block           TBrB_BPA_230k
_cod_depositor_comments
'Adding full bibliography for 7231456--7231470.cif.'
_cod_database_code               7231470
_shelx_estimated_absorpt_t_min   0.095
_shelx_estimated_absorpt_t_max   0.495
loop_
_symmetry_equiv_pos_as_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_calc_flag
Br1 Br 0.84149(14) 0.80566(4) 0.13730(3) 0.04299(17) Uani 1 d
Br2 Br 0.70634(15) 0.77201(4) -0.03386(4) 0.04634(18) Uani 1 d
Br3 Br 0.27404(13) 0.27814(4) 0.48138(3) 0.04069(16) Uani 1 d
Br4 Br 0.28962(14) 0.31632(4) 0.65597(3) 0.04208(16) Uani 1 d
N1 N 0.1191(13) -0.0390(4) 0.7689(3) 0.0484(12) Uani 1 d
N2 N 0.2592(12) 0.4531(4) 0.2646(3) 0.0443(11) Uani 1 d
C1 C 0.2626(15) -0.1107(4) 0.7362(3) 0.0493(14) Uani 1 d
H1 H 0.389959 -0.169912 0.767023 0.059 Uiso 1 calc
C2 C 0.2372(13) -0.1040(4) 0.6594(3) 0.0421(12) Uani 1 d
H2 H 0.343324 -0.15769 0.639254 0.051 Uiso 1 calc
C3 C 0.0526(12) -0.0170(4) 0.6127(3) 0.0367(11) Uani 1 d
C4 C -0.0990(13) 0.0590(4) 0.6468(3) 0.0410(12) Uani 1 d
H4 H -0.226685 0.119431 0.617474 0.049 Uiso 1 calc
C5 C -0.0600(13) 0.0447(4) 0.7235(3) 0.0421(13) Uani 1 d
H5 H -0.165092 0.096564 0.745477 0.051 Uiso 1 calc
C6 C 0.0192(13) -0.0057(4) 0.5332(3) 0.0411(12) Uani 1 d
C7 C 0.5616(11) 1.0141(3) 0.0703(3) 0.0312(10) Uani 1 d
H7 H 0.604831 1.023866 0.117674 0.037 Uiso 1 calc
C8 C 0.6458(11) 0.9169(3) 0.0572(3) 0.0287(10) Uani 1 d
C9 C 0.5875(11) 0.9028(4) -0.0129(3) 0.0311(10) Uani 1 d
C10 C 0.1242(14) 0.3781(4) 0.2426(3) 0.0444(13) Uani 1 d
H10 H 0.078697 0.31515 0.28086 0.053 Uiso 1 calc
C11 C 0.0482(13) 0.3862(4) 0.1690(3) 0.0382(12) Uani 1 d
H11 H -0.049086 0.330787 0.157992 0.046 Uiso 1 calc
C12 C 0.1161(12) 0.4768(4) 0.1109(3) 0.0325(10) Uani 1 d
C13 C 0.2613(13) 0.5571(4) 0.1314(3) 0.0375(11) Uani 1 d
H13 H 0.312051 0.620292 0.093975 0.045 Uiso 1 calc
C14 C 0.3266(14) 0.5405(4) 0.2074(3) 0.0455(14) Uani 1 d
H14 H 0.4254 0.594215 0.220337 0.055 Uiso 1 calc
C15 C 0.0340(12) 0.4929(4) 0.0325(3) 0.0356(11) Uani 1 d
C16 C 0.4925(11) 0.4851(4) 0.4275(3) 0.0326(11) Uani 1 d
H16 H 0.485983 0.474771 0.378691 0.039 Uiso 1 calc
C17 C 0.4029(11) 0.4061(3) 0.4934(3) 0.0295(10) Uani 1 d
C18 C 0.4091(11) 0.4215(4) 0.5656(3) 0.0299(10) Uani 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 0 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 N1 C5 116.5(5) . .
C14 N2 C10 115.0(5) . .
N1 C1 C2 124.2(5) . .
N1 C1 H1 117.9 . .
C2 C1 H1 117.9 . .
C3 C2 C1 118.8(5) . .
C3 C2 H2 120.6 . .
C1 C2 H2 120.6 . .
C2 C3 C4 117.2(5) . .
C2 C3 C6 121.3(5) . .
C4 C3 C6 121.5(5) . .
C5 C4 C3 119.4(5) . .
C5 C4 H4 120.3 . .
C3 C4 H4 120.3 . .
N1 C5 C4 123.8(5) . .
N1 C5 H5 118.1 . .
C4 C5 H5 118.1 . .
C6 C6 C3 177.8(8) 2_556 .
C8 C7 C9 119.5(4) . 2_675
C8 C7 H7 120.3 . .
C9 C7 H7 120.3 2_675 .
C7 C8 C9 120.3(4) . .
C7 C8 Br1 118.0(3) . .
C9 C8 Br1 121.7(3) . .
C8 C9 C7 120.2(4) . 2_675
C8 C9 Br2 121.7(4) . .
C7 C9 Br2 118.1(3) 2_675 .
N2 C10 C11 125.2(5) . .
N2 C10 H10 117.4 . .
C11 C10 H10 117.4 . .
C10 C11 C12 119.2(5) . .
C10 C11 H11 120.4 . .
C12 C11 H11 120.4 . .
C11 C12 C13 117.6(5) . .
C11 C12 C15 122.6(4) . .
C13 C12 C15 119.8(5) . .
C14 C13 C12 118.3(5) . .
C14 C13 H13 120.8 . .
C12 C13 H13 120.8 . .
N2 C14 C13 124.7(5) . .
N2 C14 H14 117.6 . .
C13 C14 H14 117.6 . .
C15 C15 C12 179.4(7) 2_565 .
C18 C16 C17 119.3(4) 2_666 .
C18 C16 H16 120.3 2_666 .
C17 C16 H16 120.3 . .
C16 C17 C18 120.5(4) . .
C16 C17 Br3 117.9(3) . .
C18 C17 Br3 121.5(4) . .
C16 C18 C17 120.2(4) 2_666 .
C16 C18 Br4 118.2(4) 2_666 .
C17 C18 Br4 121.6(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C8 1.886(4) .
Br2 C9 1.888(4) .
Br3 C17 1.898(4) .
Br4 C18 1.882(5) .
N1 C1 1.323(7) .
N1 C5 1.339(7) .
N2 C14 1.345(7) .
N2 C10 1.346(7) .
C1 C2 1.386(8) .
C1 H1 0.94 .
C2 C3 1.386(7) .
C2 H2 0.94 .
C3 C4 1.394(7) .
C3 C6 1.426(7) .
C4 C5 1.371(7) .
C4 H4 0.94 .
C5 H5 0.94 .
C6 C6 1.193(10) 2_556
C7 C8 1.381(6) .
C7 C9 1.389(6) 2_675
C7 H7 0.94 .
C8 C9 1.382(6) .
C10 C11 1.366(7) .
C10 H10 0.94 .
C11 C12 1.381(7) .
C11 H11 0.94 .
C12 C13 1.412(6) .
C12 C15 1.438(7) .
C13 C14 1.377(7) .
C13 H13 0.94 .
C14 H14 0.94 .
C15 C15 1.188(10) 2_565
C16 C18 1.379(6) 2_666
C16 C17 1.391(7) .
C16 H16 0.94 .
C17 C18 1.391(6) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139205048
