#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/30/7123022.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_7123022
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             2018-10-31T15:21:59-00:00
_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                102.747(2)
_cell_angle_beta                 92.460(2)
_cell_angle_gamma                94.329(2)
_cell_formula_units_Z            2
_cell_length_a                   3.9431(6)
_cell_length_b                   13.4500(19)
_cell_length_c                   17.231(2)
_cell_measurement_reflns_used    3778
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.86
_cell_measurement_theta_min      2.43
_cell_volume                     887.1(2)
_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      100(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '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  0.0496
_diffrn_reflns_av_unetI/netI     0.0615
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            12565
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_min         1.558
_exptl_absorpt_coefficient_mu    9.075
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.3247
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    2.156
_exptl_crystal_description       chunk
_exptl_crystal_F_000             548
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.375
_exptl_crystal_size_min          0.21
_refine_diff_density_max         0.613
_refine_diff_density_min         -0.857
_refine_diff_density_rms         0.152
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         3590
_refine_ls_number_restraints     244
_refine_ls_restrained_S_all      0.999
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.036
_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)+(0.0341P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0796
_refine_ls_wR_factor_ref         0.0869
_reflns_Friedel_coverage         0
_reflns_number_gt                2714
_reflns_number_total             3590
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc00836e2.cif
_cod_data_source_block           TBrB_BPE_100K
_cod_database_code               7123022
_shelx_estimated_absorpt_t_min   0.097
_shelx_estimated_absorpt_t_max   0.252
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 -0.28690(11) 0.71360(3) -0.02493(2) 0.01828(13) Uani 1 1 d . . . . .
Br2 Br 0.03100(11) 0.69213(3) 0.15526(2) 0.01983(14) Uani 1 1 d . . . . .
Br3 Br 0.53962(11) 0.21602(3) 0.44218(3) 0.02026(14) Uani 1 1 d . . . . .
Br4 Br 0.88615(11) 0.20221(3) 0.62229(2) 0.01904(14) Uani 1 1 d . . . . .
N1 N 0.5920(9) 0.4698(3) 0.2334(2) 0.0203(9) Uani 1 1 d . . . . .
C1 C 0.5711(11) 0.5485(4) 0.2954(2) 0.0194(11) Uani 1 1 d . . . . .
H1 H 0.466653 0.606566 0.286152 0.023 Uiso 1 1 calc R U . . .
C2 C 0.6929(10) 0.5504(3) 0.3724(2) 0.0160(10) Uani 1 1 d . . . . .
H2 H 0.667273 0.607868 0.414344 0.019 Uiso 1 1 calc R U . . .
C3 C 0.8525(10) 0.4676(3) 0.3878(2) 0.0136(10) Uani 1 1 d . . . . .
C4 C 0.8713(11) 0.3854(3) 0.3242(2) 0.0170(10) Uani 1 1 d . . . . .
H4 H 0.973648 0.326285 0.331793 0.02 Uiso 1 1 calc R U . . .
C5 C 0.7396(11) 0.3900(3) 0.2492(3) 0.0209(11) Uani 1 1 d . . . . .
H5 H 0.755764 0.332633 0.206441 0.025 Uiso 1 1 calc R U . . .
C6 C 1.0023(11) 0.4639(3) 0.4672(2) 0.0160(10) Uani 1 1 d . . . . .
H6 H 1.111146 0.404406 0.471267 0.019 Uiso 1 1 calc R U . . .
C7 C 0.1331(10) 0.4913(3) 0.0739(2) 0.0148(10) Uani 1 1 d . . . . .
H7 H 0.225052 0.485309 0.124385 0.018 Uiso 1 1 calc R U . . .
C8 C 0.0118(10) 0.5819(3) 0.0650(2) 0.0133(10) Uani 1 1 d . . . . .
C9 C -0.1204(10) 0.5905(3) -0.0092(2) 0.0144(10) Uani 1 1 d . . . . .
N2A N 0.886(2) 0.0216(4) 0.2672(3) 0.0179(12) Uani 0.935(10) 1 d . U P A 1
C10A C 0.9927(19) 0.0972(5) 0.2353(3) 0.0203(13) Uani 0.935(10) 1 d . U P A 1
H10A H 1.137822 0.15158 0.267664 0.024 Uiso 0.935(10) 1 calc R U P A 1
C11A C 0.9085(17) 0.1034(4) 0.1580(3) 0.0165(12) Uani 0.935(10) 1 d . U P A 1
H11A H 0.995104 0.160512 0.138596 0.02 Uiso 0.935(10) 1 calc R U P A 1
C12A C 0.6952(16) 0.0251(4) 0.1086(3) 0.0147(12) Uani 0.935(10) 1 d D U P A 1
C13A C 0.5841(17) -0.0550(5) 0.1415(3) 0.0170(12) Uani 0.935(10) 1 d . U P A 1
H13A H 0.437991 -0.110469 0.110818 0.02 Uiso 0.935(10) 1 calc R U P A 1
C14A C 0.686(2) -0.0542(5) 0.2193(3) 0.0175(12) Uani 0.935(10) 1 d . U P A 1
H14A H 0.609789 -0.111118 0.240169 0.021 Uiso 0.935(10) 1 calc R U P A 1
C15A C 0.6088(11) 0.0320(4) 0.0253(3) 0.0162(13) Uani 0.935(10) 1 d D U P A 1
H15A H 0.719624 0.087035 0.007181 0.019 Uiso 0.935(10) 1 calc R U P A 1
N2B N 0.87(3) 0.042(7) 0.269(3) 0.017(3) Uani 0.065(10) 1 d G U P A 2
C10B C 0.97(3) 0.108(5) 0.222(5) 0.017(3) Uani 0.065(10) 1 d G U P A 2
H10B H 1.109458 0.169069 0.244335 0.02 Uiso 0.065(10) 1 calc R U P A 2
C11B C 0.87(2) 0.084(6) 0.141(4) 0.016(3) Uani 0.065(10) 1 d G U P A 2
H11B H 0.947102 0.129174 0.108049 0.019 Uiso 0.065(10) 1 calc R U P A 2
C12B C 0.67(2) -0.006(6) 0.107(3) 0.016(2) Uani 0.065(10) 1 d DG U P A 2
C13B C 0.57(2) -0.072(5) 0.155(4) 0.016(3) Uani 0.065(10) 1 d G U P A 2
H13B H 0.428696 -0.133118 0.132139 0.019 Uiso 0.065(10) 1 calc R U P A 2
C14B C 0.66(3) -0.048(6) 0.236(4) 0.017(3) Uani 0.065(10) 1 d G U P A 2
H14B H 0.591049 -0.093225 0.268426 0.02 Uiso 0.065(10) 1 calc R U P A 2
C15B C 0.477(16) -0.023(5) 0.029(3) 0.015(3) Uani 0.065(10) 1 d D U P A 2
H15B H 0.295106 -0.075762 0.020107 0.019 Uiso 0.065(10) 1 calc R U P A 2
C16 C 0.6493(10) -0.0060(3) 0.5738(2) 0.0147(10) Uani 1 1 d . . . . .
H16 H 0.752076 -0.010257 0.623696 0.018 Uiso 1 1 calc R U . . .
C17 C 0.6628(10) 0.0860(3) 0.5505(2) 0.0142(10) Uani 1 1 d . . . . .
C18 C 0.5164(10) 0.0918(3) 0.4768(2) 0.0123(10) 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
_geom_angle_site_symmetry_3
C5 N1 C1 116.0(4) . .
N1 C1 C2 123.9(4) . .
N1 C1 H1 118.1 . .
C2 C1 H1 118.1 . .
C1 C2 C3 119.6(4) . .
C1 C2 H2 120.2 . .
C3 C2 H2 120.2 . .
C4 C3 C2 116.9(4) . .
C4 C3 C6 119.4(4) . .
C2 C3 C6 123.7(4) . .
C3 C4 C5 119.5(4) . .
C3 C4 H4 120.2 . .
C5 C4 H4 120.2 . .
N1 C5 C4 124.1(4) . .
N1 C5 H5 118 . .
C4 C5 H5 118 . .
C6 C6 C3 125.5(5) 2_766 .
C6 C6 H6 117.2 2_766 .
C3 C6 H6 117.2 . .
C8 C7 C9 119.7(4) . 2_565
C8 C7 H7 120.2 . .
C9 C7 H7 120.2 2_565 .
C7 C8 C9 119.9(4) . .
C7 C8 Br2 118.5(3) . .
C9 C8 Br2 121.6(3) . .
C7 C9 C8 120.4(4) 2_565 .
C7 C9 Br1 117.9(3) 2_565 .
C8 C9 Br1 121.6(3) . .
C10A N2A C14A 115.9(4) . .
N2A C10A C11A 124.5(5) . .
N2A C10A H10A 117.7 . .
C11A C10A H10A 117.7 . .
C10A C11A C12A 119.5(5) . .
C10A C11A H11A 120.2 . .
C12A C11A H11A 120.2 . .
C13A C12A C11A 116.3(4) . .
C13A C12A C15A 124.6(5) . .
C11A C12A C15A 119.2(4) . .
C12A C13A C14A 119.6(5) . .
C12A C13A H13A 120.2 . .
C14A C13A H13A 120.2 . .
N2A C14A C13A 124.2(5) . .
N2A C14A H14A 117.9 . .
C13A C14A H14A 117.9 . .
C15A C15A C12A 125.3(6) 2_655 .
C15A C15A H15A 117.3 2_655 .
C12A C15A H15A 117.3 . .
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 114(5) . .
C11B C12B C15B 123(5) . .
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 129(7) 2_655 .
C15B C15B H15B 115.6 2_655 .
C12B C15B H15B 115.6 . .
C17 C16 C18 118.8(4) . 2_656
C17 C16 H16 120.6 . .
C18 C16 H16 120.6 2_656 .
C16 C17 C18 120.5(4) . .
C16 C17 Br4 117.5(3) . .
C18 C17 Br4 122.0(3) . .
C16 C18 C17 120.7(4) 2_656 .
C16 C18 Br3 117.8(3) 2_656 .
C17 C18 Br3 121.5(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C9 1.895(4) .
Br2 C8 1.891(4) .
Br3 C18 1.892(4) .
Br4 C17 1.896(4) .
N1 C5 1.333(5) .
N1 C1 1.338(5) .
C1 C2 1.385(5) .
C1 H1 0.95 .
C2 C3 1.388(6) .
C2 H2 0.95 .
C3 C4 1.384(6) .
C3 C6 1.478(5) .
C4 C5 1.388(5) .
C4 H4 0.95 .
C5 H5 0.95 .
C6 C6 1.321(8) 2_766
C6 H6 0.95 .
C7 C8 1.379(5) .
C7 C9 1.380(5) 2_565
C7 H7 0.95 .
C8 C9 1.392(5) .
N2A C10A 1.308(6) .
N2A C14A 1.340(6) .
C10A C11A 1.381(6) .
C10A H10A 0.95 .
C11A C12A 1.397(6) .
C11A H11A 0.95 .
C12A C13A 1.376(6) .
C12A C15A 1.484(6) .
C13A C14A 1.381(6) .
C13A H13A 0.95 .
C14A H14A 0.95 .
C15A C15A 1.316(9) 2_655
C15A H15A 0.95 .
N2B C10B 1.39 .
N2B C14B 1.41(13) .
C10B C11B 1.39 .
C10B H10B 0.95 .
C11B C12B 1.39 .
C11B H11B 0.95 .
C12B C13B 1.39 .
C12B C15B 1.49(3) .
C13B C14B 1.39 .
C13B H13B 0.95 .
C14B H14B 0.95 .
C15B C15B 1.31(3) 2_655
C15B H15B 0.95 .
C16 C17 1.380(5) .
C16 C18 1.383(5) 2_656
C16 H16 0.95 .
C17 C18 1.392(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 0.95 2.38 3.303(5) 164.8 .
C16 H16 N2A 0.95 2.35 3.285(6) 167.8 2_756
C16 H16 N2B 0.95 2.46 3.39(7) 164.9 2_756
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139189548
