#------------------------------------------------------------------------------
#$Date: 2025-08-22 23:12:46 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301866 $
#$URL: svn://www.crystallography.net/cod/cif/7/23/14/7231458.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_7231458
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             2018-01-23T12:23:47-00:00
_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                 111.344(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.1069(5)
_cell_length_b                   5.2772(2)
_cell_length_c                   11.2674(4)
_cell_measurement_reflns_used    3110
_cell_measurement_temperature    249(2)
_cell_measurement_theta_max      27.14
_cell_measurement_theta_min      3.62
_cell_volume                     836.65(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      249(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  0.0410
_diffrn_reflns_av_unetI/netI     0.0386
_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            11205
_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         31.557
_diffrn_reflns_theta_min         2.895
_exptl_absorpt_coefficient_mu    4.89
_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    1.937
_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         0.331
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.083
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     118
_refine_ls_number_reflns         2797
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0294
_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)+(0.0269P)²+0.0789P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0584
_refine_ls_wR_factor_ref         0.0641
_reflns_number_gt                2121
_reflns_number_total             2797
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c8ce01090k2.cif
_cod_data_source_block           diBrBPA_250k
_cod_depositor_comments
'Adding full bibliography for 7231456--7231470.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7231458
_shelx_estimated_absorpt_t_min   0.312
_shelx_estimated_absorpt_t_max   0.49
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 0.34239(2) 0.43268(4) 0.85433(2) 0.03059(7) Uani 1 d
F2 F 0.33872(9) 0.0401(3) 1.05015(13) 0.0448(3) Uani 1 d
F1 F 0.53271(9) 0.3103(3) 0.82933(12) 0.0439(3) Uani 1 d
C9 C 0.02589(14) 0.4176(4) 0.52849(19) 0.0303(4) Uani 1 d
C4 C 0.21623(16) -0.0676(4) 0.6252(2) 0.0397(5) Uani 1 d
H4 H 0.2633 -0.1298 0.5966 0.048 Uiso 1 calc
C1 C 0.43255(13) 0.1835(4) 0.93652(16) 0.0248(4) Uani 1 d
N1 N 0.21017(13) -0.1697(4) 0.73002(18) 0.0378(4) Uani 1 d
C8 C 0.14384(16) -0.0754(4) 0.7687(2) 0.0374(5) Uani 1 d
H8 H 0.1386 -0.1434 0.8429 0.045 Uiso 1 calc
C2 C 0.51529(14) 0.1561(4) 0.91261(17) 0.0275(4) Uani 1 d
C6 C 0.08857(13) 0.2185(4) 0.59688(17) 0.0271(4) Uani 1 d
C3 C 0.41876(14) 0.0240(4) 1.02511(18) 0.0276(4) Uani 1 d
C5 C 0.15806(15) 0.1231(4) 0.5562(2) 0.0338(5) Uani 1 d
H5 H 0.1654 0.1875 0.4825 0.041 Uiso 1 calc
C7 C 0.08219(15) 0.1158(4) 0.7070(2) 0.0331(5) Uani 1 d
H7 H 0.0366 0.1756 0.7388 0.04 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(3) 3_566 .
N1 C4 C5 124.2(2) . .
N1 C4 H4 117.9 . .
C5 C4 H4 117.9 . .
C3 C1 C2 117.66(18) . .
C3 C1 Br1 120.76(15) . .
C2 C1 Br1 121.58(15) . .
C8 N1 C4 116.34(18) . .
N1 C8 C7 124.2(2) . .
N1 C8 H8 117.9 . .
C7 C8 H8 117.9 . .
F1 C2 C3 119.25(18) . 3_657
F1 C2 C1 119.79(18) . .
C3 C2 C1 120.95(18) 3_657 .
C5 C6 C7 117.46(18) . .
C5 C6 C9 121.32(18) . .
C7 C6 C9 121.22(18) . .
F2 C3 C2 118.65(17) . 3_657
F2 C3 C1 119.95(18) . .
C2 C3 C1 121.39(18) 3_657 .
C4 C5 C6 119.0(2) . .
C4 C5 H5 120.5 . .
C6 C5 H5 120.5 . .
C8 C7 C6 118.87(19) . .
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 1.8771(18) .
F2 C3 1.341(2) .
F1 C2 1.338(2) .
C9 C9 1.190(4) 3_566
C9 C6 1.436(3) .
C4 N1 1.331(3) .
C4 C5 1.376(3) .
C4 H4 0.94 .
C1 C3 1.378(3) .
C1 C2 1.379(3) .
N1 C8 1.326(3) .
C8 C7 1.377(3) .
C8 H8 0.94 .
C2 C3 1.371(3) 3_657
C6 C5 1.384(3) .
C6 C7 1.389(3) .
C3 C2 1.371(3) 3_657
C5 H5 0.94 .
C7 H7 0.94 .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139205046
