#------------------------------------------------------------------------------
#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/14/7231460.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_7231460
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 H8 Br2 F4 N2'
_chemical_formula_weight         488.08
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2018-01-23T12:36:54-00:00
_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                90
_cell_angle_beta                 111.348(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.1283(5)
_cell_length_b                   5.27450(10)
_cell_length_c                   11.2948(4)
_cell_measurement_reflns_used    3012
_cell_measurement_temperature    269(2)
_cell_measurement_theta_max      26.85
_cell_measurement_theta_min      3.61
_cell_volume                     839.42(5)
_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 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      269(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_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  0.0407
_diffrn_reflns_av_unetI/netI     0.0370
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11249
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.555
_diffrn_reflns_theta_min         2.891
_exptl_absorpt_coefficient_mu    4.874
_exptl_absorpt_correction_T_max  0.3782
_exptl_absorpt_correction_T_min  0.2660
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.931
_exptl_crystal_description       rod
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.418
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.082
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.02
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         2808
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.02
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0303
_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)+(0.0270P)²+0.2006P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0596
_refine_ls_wR_factor_ref         0.0664
_reflns_number_gt                2098
_reflns_number_total             2808
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce01090k2.cif
_cod_data_source_block           diBrBPA_270k
_cod_depositor_comments
'Adding full bibliography for 7231456--7231470.cif.'
_cod_original_cell_volume        839.42(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7231460
_shelx_estimated_absorpt_t_min   0.313
_shelx_estimated_absorpt_t_max   0.491
loop_
_symmetry_equiv_pos_as_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_calc_flag
Br1 Br 0.34259(2) 0.43240(4) 0.85417(2) 0.03354(8) Uani 1 d
F2 F 0.33902(10) 0.0412(3) 1.05004(14) 0.0486(4) Uani 1 d
F1 F 0.53282(10) 0.3093(3) 0.82938(12) 0.0478(4) Uani 1 d
C9 C 0.02601(15) 0.4177(4) 0.5284(2) 0.0329(4) Uani 1 d
C4 C 0.21602(17) -0.0678(4) 0.6251(2) 0.0430(6) Uani 1 d
H4 H 0.2624 -0.1298 0.5968 0.052 Uiso 1 calc
C1 C 0.43252(14) 0.1840(4) 0.93641(17) 0.0277(4) Uani 1 d
C8 C 0.14395(17) -0.0750(4) 0.7684(2) 0.0406(5) Uani 1 d
H8 H 0.1389 -0.1421 0.8419 0.049 Uiso 1 calc
N1 N 0.21008(14) -0.1689(4) 0.72957(19) 0.0415(5) Uani 1 d
C2 C 0.51499(15) 0.1557(4) 0.91250(18) 0.0297(4) Uani 1 d
C6 C 0.08863(14) 0.2188(4) 0.59652(18) 0.0296(4) Uani 1 d
C3 C 0.41895(15) 0.0240(4) 1.02509(19) 0.0304(4) Uani 1 d
C5 C 0.15786(16) 0.1230(4) 0.5560(2) 0.0371(5) Uani 1 d
H5 H 0.1651 0.1864 0.4832 0.045 Uiso 1 calc
C7 C 0.08212(16) 0.1160(4) 0.7065(2) 0.0363(5) Uani 1 d
H7 H 0.0369 0.1751 0.7377 0.044 Uiso 1 calc
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'
F F 0.0171 0.0103 '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
C9 C9 C6 179.8(4) 3_566 .
N1 C4 C5 124.2(2) . .
N1 C4 H4 117.9 . .
C5 C4 H4 117.9 . .
C2 C1 C3 117.41(18) . .
C2 C1 Br1 121.66(15) . .
C3 C1 Br1 120.93(15) . .
N1 C8 C7 124.0(2) . .
N1 C8 H8 118 . .
C7 C8 H8 118 . .
C8 N1 C4 116.60(19) . .
F1 C2 C3 118.89(19) . 3_657
F1 C2 C1 119.97(19) . .
C3 C2 C1 121.12(19) 3_657 .
C5 C6 C7 117.51(19) . .
C5 C6 C9 121.4(2) . .
C7 C6 C9 121.07(19) . .
F2 C3 C2 118.87(18) . 3_657
F2 C3 C1 119.65(19) . .
C2 C3 C1 121.47(19) 3_657 .
C4 C5 C6 118.9(2) . .
C4 C5 H5 120.5 . .
C6 C5 H5 120.5 . .
C8 C7 C6 118.8(2) . .
C8 C7 H7 120.6 . .
C6 C7 H7 120.6 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C1 1.873(2) .
F2 C3 1.341(2) .
F1 C2 1.340(2) .
C9 C9 1.190(4) 3_566
C9 C6 1.435(3) .
C4 N1 1.327(3) .
C4 C5 1.377(3) .
C4 H4 0.93 .
C1 C2 1.377(3) .
C1 C3 1.381(3) .
C8 N1 1.326(3) .
C8 C7 1.380(3) .
C8 H8 0.93 .
C2 C3 1.371(3) 3_657
C6 C5 1.382(3) .
C6 C7 1.391(3) .
C3 C2 1.371(3) 3_657
C5 H5 0.93 .
C7 H7 0.93 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139205046
