#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/30/7123021.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_7123021
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             2018-10-31T15:20:17-00:00
_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                102.795(2)
_cell_angle_beta                 93.323(2)
_cell_angle_gamma                94.316(2)
_cell_formula_units_Z            2
_cell_length_a                   3.9924(2)
_cell_length_b                   13.5015(6)
_cell_length_c                   17.3091(8)
_cell_measurement_reflns_used    4393
_cell_measurement_temperature    249(2)
_cell_measurement_theta_max      26.81
_cell_measurement_theta_min      2.42
_cell_volume                     904.59(7)
_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      249(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_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  0.0335
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_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            14191
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.561
_diffrn_reflns_theta_min         1.553
_exptl_absorpt_coefficient_mu    8.9
_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    2.114
_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         0.327
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4155
_refine_ls_number_restraints     244
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0275
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0179P)²+0.2285P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0523
_refine_ls_wR_factor_ref         0.0581
_reflns_Friedel_coverage         0
_reflns_number_gt                3022
_reflns_number_total             4155
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc00836e2.cif
_cod_data_source_block           TBrB_BPE_250K
_cod_database_code               7123021
_shelx_estimated_absorpt_t_min   0.103
_shelx_estimated_absorpt_t_max   0.302
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 -0.28281(7) 0.71177(2) -0.02545(2) 0.04445(9) Uani 1 1 d . . . . .
Br2 Br 0.03655(8) 0.69118(2) 0.15411(2) 0.04846(10) Uani 1 1 d . . . . .
Br3 Br 0.54142(8) 0.21533(2) 0.44410(2) 0.04852(10) Uani 1 1 d . . . . .
Br4 Br 0.88543(7) 0.19962(2) 0.62326(2) 0.04595(9) Uani 1 1 d . . . . .
N1 N 0.5899(7) 0.4698(2) 0.23503(15) 0.0498(7) Uani 1 1 d . . . . .
C1 C 0.5739(8) 0.5479(2) 0.29592(18) 0.0450(8) Uani 1 1 d . . . . .
H1 H 0.471391 0.60492 0.286271 0.054 Uiso 1 1 calc R U . . .
C2 C 0.6979(7) 0.5512(2) 0.37257(16) 0.0371(7) Uani 1 1 d . . . . .
H2 H 0.676887 0.608391 0.413672 0.045 Uiso 1 1 calc R U . . .
C3 C 0.8544(6) 0.4684(2) 0.38799(16) 0.0328(6) Uani 1 1 d . . . . .
C4 C 0.8686(8) 0.3869(2) 0.32497(17) 0.0444(7) Uani 1 1 d . . . . .
H4 H 0.968091 0.328459 0.332546 0.053 Uiso 1 1 calc R U . . .
C5 C 0.7365(8) 0.3913(3) 0.25085(19) 0.0524(9) Uani 1 1 d . . . . .
H5 H 0.751469 0.334796 0.208675 0.063 Uiso 1 1 calc R U . . .
C6 C 1.0020(7) 0.4648(2) 0.46714(16) 0.0365(7) Uani 1 1 d . . . . .
H6 H 1.109796 0.406322 0.470998 0.044 Uiso 1 1 calc R U . . .
C7 C 0.1344(6) 0.4916(2) 0.07370(16) 0.0330(6) Uani 1 1 d . . . . .
H7 H 0.226149 0.485946 0.123609 0.04 Uiso 1 1 calc R U . . .
C8 C 0.0142(6) 0.5818(2) 0.06427(15) 0.0318(6) Uani 1 1 d . . . . .
C9 C -0.1185(6) 0.5898(2) -0.00935(16) 0.0304(6) Uani 1 1 d . . . . .
N2A N 0.8856(14) 0.0228(3) 0.2656(2) 0.0474(12) Uani 0.928(8) 1 d . U P A 1
C10A C 0.9904(14) 0.0984(4) 0.2341(3) 0.0483(13) Uani 0.928(8) 1 d . U P A 1
H10A H 1.132884 0.152224 0.26628 0.058 Uiso 0.928(8) 1 calc R U P A 1
C11A C 0.9054(13) 0.1040(4) 0.1571(2) 0.0435(11) Uani 0.928(8) 1 d . U P A 1
H11A H 0.988596 0.160366 0.138089 0.052 Uiso 0.928(8) 1 calc R U P A 1
C12A C 0.6983(11) 0.0267(3) 0.1082(2) 0.0353(10) Uani 0.928(8) 1 d D U P A 1
C13A C 0.5868(12) -0.0540(3) 0.1406(2) 0.0408(11) Uani 0.928(8) 1 d . U P A 1
H13A H 0.444683 -0.109086 0.109917 0.049 Uiso 0.928(8) 1 calc R U P A 1
C14A C 0.6876(13) -0.0521(4) 0.2183(2) 0.0458(11) Uani 0.928(8) 1 d . U P A 1
H14A H 0.610942 -0.107508 0.239185 0.055 Uiso 0.928(8) 1 calc R U P A 1
C15A C 0.6070(7) 0.0319(3) 0.02522(19) 0.0372(10) Uani 0.928(8) 1 d D U P A 1
H15A H 0.712996 0.086101 0.007154 0.045 Uiso 0.928(8) 1 calc R U P A 1
N2B N 0.932(18) 0.046(5) 0.267(2) 0.042(5) Uani 0.072(8) 1 d G U P A 2
C10B C 0.988(17) 0.114(4) 0.219(4) 0.039(5) Uani 0.072(8) 1 d G U P A 2
H10B H 1.122516 0.175934 0.238641 0.047 Uiso 0.072(8) 1 calc R U P A 2
C11B C 0.846(17) 0.091(5) 0.141(4) 0.035(5) Uani 0.072(8) 1 d G U P A 2
H11B H 0.884027 0.137573 0.108232 0.042 Uiso 0.072(8) 1 calc R U P A 2
C12B C 0.648(15) 0.000(5) 0.111(2) 0.034(4) Uani 0.072(8) 1 d DG U P A 2
C13B C 0.592(14) -0.068(4) 0.160(3) 0.035(5) Uani 0.072(8) 1 d G U P A 2
H13B H 0.457654 -0.129859 0.139729 0.042 Uiso 0.072(8) 1 calc R U P A 2
C14B C 0.734(17) -0.045(5) 0.237(3) 0.040(5) Uani 0.072(8) 1 d G U P A 2
H14B H 0.696141 -0.0915 0.270139 0.049 Uiso 0.072(8) 1 calc R U P A 2
C15B C 0.497(10) -0.025(3) 0.0277(18) 0.032(6) Uani 0.072(8) 1 d D U P A 2
H15B H 0.372824 -0.088976 0.012649 0.038 Uiso 0.072(8) 1 calc R U P A 2
C16 C 0.6449(6) -0.0072(2) 0.57295(15) 0.0307(6) Uani 1 1 d . . . . .
H16 H 0.743532 -0.011837 0.622536 0.037 Uiso 1 1 calc R U . . .
C17 C 0.6630(6) 0.0847(2) 0.55075(15) 0.0301(6) Uani 1 1 d . . . . .
C18 C 0.5181(6) 0.0922(2) 0.47780(15) 0.0288(6) 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 116.1(3) .
N1 C1 C2 124.2(3) .
N1 C1 H1 117.9 .
C2 C1 H1 117.9 .
C1 C2 C3 118.9(3) .
C1 C2 H2 120.6 .
C3 C2 H2 120.6 .
C4 C3 C2 117.0(2) .
C4 C3 C6 119.7(3) .
C2 C3 C6 123.4(3) .
C5 C4 C3 119.6(3) .
C5 C4 H4 120.2 .
C3 C4 H4 120.2 .
N1 C5 C4 124.2(3) .
N1 C5 H5 117.9 .
C4 C5 H5 117.9 .
C6 C6 C3 126.4(3) 2_766
C6 C6 H6 116.8 2_766
C3 C6 H6 116.8 .
C9 C7 C8 119.4(2) 2_565
C9 C7 H7 120.3 2_565
C8 C7 H7 120.3 .
C7 C8 C9 120.0(2) .
C7 C8 Br2 118.1(2) .
C9 C8 Br2 122.0(2) .
C7 C9 C8 120.6(2) 2_565
C7 C9 Br1 117.78(19) 2_565
C8 C9 Br1 121.6(2) .
C10A N2A C14A 116.1(3) .
N2A C10A C11A 124.3(3) .
N2A C10A H10A 117.9 .
C11A C10A H10A 117.9 .
C12A C11A C10A 119.6(4) .
C12A C11A H11A 120.2 .
C10A C11A H11A 120.2 .
C11A C12A C13A 116.7(3) .
C11A C12A C15A 120.0(3) .
C13A C12A C15A 123.3(3) .
C14A C13A C12A 118.9(3) .
C14A C13A H13A 120.5 .
C12A C13A H13A 120.5 .
N2A C14A C13A 124.3(4) .
N2A C14A H14A 117.8 .
C13A C14A H14A 117.8 .
C15A C15A C12A 126.1(5) 2_655
C15A C15A H15A 117 2_655
C12A C15A H15A 117 .
C10B N2B C14B 120 .
N2B C10B C11B 120 .
N2B C10B H10B 120 .
C11B C10B H10B 120 .
C12B C11B C10B 120 .
C12B C11B H11B 120 .
C10B C11B H11B 120 .
C13B C12B C11B 120 .
C13B C12B C15B 120(4) .
C11B C12B C15B 120(4) .
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 132(5) 2_655
C15B C15B H15B 113.9 2_655
C12B C15B H15B 113.9 .
C18 C16 C17 119.6(2) 2_656
C18 C16 H16 120.2 2_656
C17 C16 H16 120.2 .
C16 C17 C18 120.6(2) .
C16 C17 Br4 117.91(19) .
C18 C17 Br4 121.5(2) .
C16 C18 C17 119.9(2) 2_656
C16 C18 Br3 117.91(19) 2_656
C17 C18 Br3 122.2(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C9 1.888(3) .
Br2 C8 1.885(3) .
Br3 C18 1.878(3) .
Br4 C17 1.890(2) .
N1 C5 1.320(4) .
N1 C1 1.324(4) .
C1 C2 1.379(4) .
C1 H1 0.94 .
C2 C3 1.388(4) .
C2 H2 0.94 .
C3 C4 1.375(4) .
C3 C6 1.472(4) .
C4 C5 1.374(4) .
C4 H4 0.94 .
C5 H5 0.94 .
C6 C6 1.313(5) 2_766
C6 H6 0.94 .
C7 C9 1.376(4) 2_565
C7 C8 1.381(4) .
C7 H7 0.94 .
C8 C9 1.381(3) .
N2A C10A 1.312(5) .
N2A C14A 1.325(5) .
C10A C11A 1.376(5) .
C10A H10A 0.94 .
C11A C12A 1.374(5) .
C11A H11A 0.94 .
C12A C13A 1.388(5) .
C12A C15A 1.479(4) .
C13A C14A 1.375(5) .
C13A H13A 0.94 .
C14A H14A 0.94 .
C15A C15A 1.305(6) 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 1.373(3) 2_656
C16 C17 1.376(4) .
C16 H16 0.94 .
C17 C18 1.385(3) .
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 2.41 3.324(3) 165.7 .
C16 H16 N2A 0.94 2.41 3.328(4) 166.8 2_756
C16 H16 N2B 0.94 2.39 3.32(4) 168.3 2_756
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139189548
