#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/30/7123024.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_7123024
loop_
_publ_author_name
'Crawford, Adam W.'
'Groeneman , Ryan'
'Unruh, Daniel K.'
'Hutchins, Kristin M.'
_publ_section_title
;
 Cooling-rate dependent single-crystal-to-single-crystal phase transition
 in an organic co-crystal
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/C9CC00836E
_journal_year                    2019
_chemical_formula_sum            'C18 H12 Br4 N2'
_chemical_formula_weight         575.94
_space_group_IT_number           2
_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             2018-10-31T15:20:46-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2019-01-09 deposited with the CCDC.    2019-02-21 downloaded from the CCDC.
;
_cell_angle_alpha                102.810(2)
_cell_angle_beta                 93.204(2)
_cell_angle_gamma                94.321(2)
_cell_formula_units_Z            2
_cell_length_a                   3.9826(2)
_cell_length_b                   13.4966(7)
_cell_length_c                   17.2973(8)
_cell_measurement_reflns_used    4641
_cell_measurement_temperature    229(2)
_cell_measurement_theta_max      27.32
_cell_measurement_theta_min      2.42
_cell_volume                     901.52(8)
_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 0.999
_diffrn_measured_fraction_theta_max 0.99
_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  0.0837
_diffrn_reflns_av_unetI/netI     0.0646
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.99
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            14172
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.99
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.575
_diffrn_reflns_theta_min         1.554
_exptl_absorpt_coefficient_mu    8.93
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_correction_T_min  0.5748
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.122
_exptl_crystal_description       rod
_exptl_crystal_F_000             548
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.468
_exptl_crystal_size_mid          0.202
_exptl_crystal_size_min          0.177
_refine_diff_density_max         1.225
_refine_diff_density_min         -1.13
_refine_diff_density_rms         0.146
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4140
_refine_ls_number_restraints     244
_refine_ls_restrained_S_all      0.908
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0411
_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)+(0.0461P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.0994
_reflns_Friedel_coverage         0
_reflns_number_gt                2762
_reflns_number_total             4140
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc00836e2.cif
_cod_data_source_block           TBrB_BPE_230K
_cod_original_cell_volume        901.51(8)
_cod_database_code               7123024
_shelx_estimated_absorpt_t_min   0.103
_shelx_estimated_absorpt_t_max   0.301
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.28331(11) 0.71197(3) -0.02543(3) 0.04047(14) Uani 1 1 d . . . . .
Br2 Br 0.03756(12) 0.69158(4) 0.15419(3) 0.04394(15) Uani 1 1 d . . . . .
Br3 Br 0.54248(12) 0.21551(3) 0.44405(3) 0.04431(15) Uani 1 1 d . . . . .
Br4 Br 0.88595(11) 0.19968(3) 0.62334(3) 0.04198(14) Uani 1 1 d . . . . .
N1 N 0.5901(10) 0.4700(3) 0.2345(2) 0.0456(10) Uani 1 1 d . . . . .
C1 C 0.5738(11) 0.5481(4) 0.2961(3) 0.0411(11) Uani 1 1 d . . . . .
H1 H 0.470902 0.605336 0.286965 0.049 Uiso 1 1 calc R U . . .
C2 C 0.6982(10) 0.5505(3) 0.3726(2) 0.0348(10) Uani 1 1 d . . . . .
H2 H 0.676473 0.607351 0.414076 0.042 Uiso 1 1 calc R U . . .
C3 C 0.8550(10) 0.4681(3) 0.3874(2) 0.0301(9) Uani 1 1 d . . . . .
C4 C 0.8700(11) 0.3868(3) 0.3253(3) 0.0408(11) Uani 1 1 d . . . . .
H4 H 0.968481 0.328336 0.333117 0.049 Uiso 1 1 calc R U . . .
C5 C 0.7383(12) 0.3914(4) 0.2503(3) 0.0472(12) Uani 1 1 d . . . . .
H5 H 0.755218 0.335053 0.208044 0.057 Uiso 1 1 calc R U . . .
C6 C 1.0025(10) 0.4651(3) 0.4674(2) 0.0323(10) Uani 1 1 d . . . . .
H6 H 1.110608 0.4067 0.471493 0.039 Uiso 1 1 calc R U . . .
C7 C 0.1354(9) 0.4913(3) 0.0733(2) 0.0299(9) Uani 1 1 d . . . . .
H7 H 0.228161 0.485561 0.123142 0.036 Uiso 1 1 calc R U . . .
C8 C 0.0153(9) 0.5819(3) 0.0644(2) 0.0301(9) Uani 1 1 d . . . . .
C9 C -0.1190(9) 0.5895(3) -0.0098(2) 0.0285(9) Uani 1 1 d . . . . .
N2A N 0.8851(15) 0.0237(5) 0.2666(3) 0.0423(14) Uani 0.948(10) 1 d . U P A 1
C10A C 0.9915(19) 0.0985(5) 0.2344(4) 0.0452(16) Uani 0.948(10) 1 d . U P A 1
H10A H 1.134906 0.152428 0.266239 0.054 Uiso 0.948(10) 1 calc R U P A 1
C11A C 0.9073(17) 0.1034(5) 0.1569(4) 0.0397(15) Uani 0.948(10) 1 d . U P A 1
H11A H 0.9918 0.159321 0.137351 0.048 Uiso 0.948(10) 1 calc R U P A 1
C12A C 0.699(2) 0.0259(6) 0.1086(3) 0.0343(11) Uani 0.948(10) 1 d D U P A 1
C13A C 0.5841(15) -0.0542(5) 0.1416(4) 0.0374(15) Uani 0.948(10) 1 d . U P A 1
H13A H 0.439163 -0.108975 0.111388 0.045 Uiso 0.948(10) 1 calc R U P A 1
C14A C 0.6870(14) -0.0515(5) 0.2194(4) 0.0393(14) Uani 0.948(10) 1 d . U P A 1
H14A H 0.611436 -0.106879 0.24059 0.047 Uiso 0.948(10) 1 calc R U P A 1
C15A C 0.6061(11) 0.0316(4) 0.0253(3) 0.0339(14) Uani 0.948(10) 1 d D U P A 1
H15A H 0.711034 0.086419 0.007611 0.041 Uiso 0.948(10) 1 calc R U P A 1
N2B N 0.94(3) 0.030(10) 0.256(5) 0.038(5) Uani 0.052(10) 1 d G U P A 2
C10B C 0.97(3) 0.116(8) 0.224(6) 0.039(5) Uani 0.052(10) 1 d G U P A 2
H10B H 1.080336 0.178009 0.255019 0.046 Uiso 0.052(10) 1 calc R U P A 2
C11B C 0.84(4) 0.111(9) 0.147(7) 0.037(5) Uani 0.052(10) 1 d G U P A 2
H11B H 0.861928 0.169177 0.125621 0.044 Uiso 0.052(10) 1 calc R U P A 2
C12B C 0.68(3) 0.020(10) 0.102(5) 0.035(4) Uani 0.052(10) 1 d DG U P A 2
C13B C 0.65(3) -0.066(8) 0.134(7) 0.035(5) Uani 0.052(10) 1 d G U P A 2
H13B H 0.545242 -0.127696 0.103023 0.042 Uiso 0.052(10) 1 calc R U P A 2
C14B C 0.78(3) -0.061(8) 0.211(7) 0.037(5) Uani 0.052(10) 1 d G U P A 2
H14B H 0.763648 -0.118866 0.232421 0.045 Uiso 0.052(10) 1 calc R U P A 2
C15B C 0.50(2) -0.031(5) 0.024(4) 0.034(6) Uani 0.052(10) 1 d D U P A 2
H15B H 0.401297 -0.098395 0.01077 0.04 Uiso 0.052(10) 1 calc R U P A 2
C16 C 0.6459(9) -0.0074(3) 0.5725(2) 0.0285(9) Uani 1 1 d . . . . .
H16 H 0.745785 -0.012265 0.621947 0.034 Uiso 1 1 calc R U . . .
C17 C 0.6631(9) 0.0855(3) 0.5510(2) 0.0275(9) Uani 1 1 d . . . . .
C18 C 0.5164(9) 0.0922(3) 0.4779(2) 0.0276(9) 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 0 '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'
N N 0.0061 0.0033 '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
C5 N1 C1 115.8(4) .
N1 C1 C2 124.1(4) .
N1 C1 H1 117.9 .
C2 C1 H1 117.9 .
C1 C2 C3 119.0(4) .
C1 C2 H2 120.5 .
C3 C2 H2 120.5 .
C4 C3 C2 117.6(4) .
C4 C3 C6 119.7(4) .
C2 C3 C6 122.7(4) .
C3 C4 C5 119.3(4) .
C3 C4 H4 120.4 .
C5 C4 H4 120.4 .
N1 C5 C4 124.1(4) .
N1 C5 H5 117.9 .
C4 C5 H5 117.9 .
C6 C6 C3 126.7(5) 2_766
C6 C6 H6 116.7 2_766
C3 C6 H6 116.7 .
C9 C7 C8 119.8(4) 2_565
C9 C7 H7 120.1 2_565
C8 C7 H7 120.1 .
C7 C8 C9 119.4(4) .
C7 C8 Br2 118.5(3) .
C9 C8 Br2 122.1(3) .
C7 C9 C8 120.8(4) 2_565
C7 C9 Br1 118.1(3) 2_565
C8 C9 Br1 121.1(3) .
C10A N2A C14A 115.9(4) .
N2A C10A C11A 124.5(5) .
N2A C10A H10A 117.8 .
C11A C10A H10A 117.8 .
C12A C11A C10A 119.4(5) .
C12A C11A H11A 120.3 .
C10A C11A H11A 120.3 .
C11A C12A C13A 117.1(4) .
C11A C12A C15A 119.4(6) .
C13A C12A C15A 123.5(6) .
C14A C13A C12A 118.5(4) .
C14A C13A H13A 120.7 .
C12A C13A H13A 120.7 .
N2A C14A C13A 124.6(5) .
N2A C14A H14A 117.7 .
C13A C14A H14A 117.7 .
C15A C15A C12A 126.4(7) 2_655
C15A C15A H15A 116.8 2_655
C12A C15A H15A 116.8 .
C10B N2B C14B 120 .
C11B C10B N2B 120.00(7) .
C11B C10B H10B 120 .
N2B C10B H10B 120 .
C10B C11B C12B 120 .
C10B C11B H11B 120 .
C12B C11B H11B 120 .
C13B C12B C11B 120 .
C13B C12B C15B 95(8) .
C11B C12B C15B 145(8) .
C12B C13B C14B 120 .
C12B C13B H13B 120 .
C14B C13B H13B 120 .
C13B C14B N2B 120 .
C13B C14B H14B 120 .
N2B C14B H14B 120 .
C15B C15B C12B 111(8) 2_655
C15B C15B H15B 124.7 2_655
C12B C15B H15B 124.7 .
C18 C16 C17 120.1(4) 2_656
C18 C16 H16 120 2_656
C17 C16 H16 120 .
C16 C17 C18 119.8(3) .
C16 C17 Br4 118.1(3) .
C18 C17 Br4 122.1(3) .
C16 C18 C17 120.1(4) 2_656
C16 C18 Br3 118.1(3) 2_656
C17 C18 Br3 121.7(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C9 1.891(4) .
Br2 C8 1.886(4) .
Br3 C18 1.880(4) .
Br4 C17 1.883(4) .
N1 C5 1.325(6) .
N1 C1 1.331(6) .
C1 C2 1.379(6) .
C1 H1 0.94 .
C2 C3 1.380(6) .
C2 H2 0.94 .
C3 C4 1.363(6) .
C3 C6 1.483(5) .
C4 C5 1.387(6) .
C4 H4 0.94 .
C5 H5 0.94 .
C6 C6 1.301(8) 2_766
C6 H6 0.94 .
C7 C9 1.360(5) 2_565
C7 C8 1.383(5) .
C7 H7 0.94 .
C8 C9 1.390(5) .
N2A C10A 1.312(7) .
N2A C14A 1.326(6) .
C10A C11A 1.381(6) .
C10A H10A 0.94 .
C11A C12A 1.372(6) .
C11A H11A 0.94 .
C12A C13A 1.390(6) .
C12A C15A 1.487(7) .
C13A C14A 1.377(6) .
C13A H13A 0.94 .
C14A H14A 0.94 .
C15A C15A 1.299(8) 2_655
C15A H15A 0.94 .
N2B C10B 1.39 .
N2B C14B 1.39 .
C10B C11B 1.39 .
C10B H10B 0.94 .
C11B C12B 1.39 .
C11B H11B 0.94 .
C12B C13B 1.39 .
C12B C15B 1.49(3) .
C13B C14B 1.39 .
C13B H13B 0.94 .
C14B H14B 0.94 .
C15B C15B 1.29(3) 2_655
C15B H15B 0.94 .
C16 C18 1.368(5) 2_656
C16 C17 1.383(5) .
C16 H16 0.94 .
C17 C18 1.387(5) .
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H7 N1 0.94 2.4 3.318(5) 166.1 .
C16 H16 N2A 0.94 2.4 3.321(6) 167.2 2_756
C16 H16 N2B 0.94 2.45 3.39(8) 174.2 2_756
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139189548
