#------------------------------------------------------------------------------
#$Date: 2025-08-22 10:56:18 +0200 (Fri 22 de Aug de 2025) $
#$Revision: 301860 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/30/7123019.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_7123019
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             2018-10-31T14:43:28-00:00
_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                102.786(3)
_cell_angle_beta                 93.568(3)
_cell_angle_gamma                94.296(3)
_cell_formula_units_Z            2
_cell_length_a                   4.0143(2)
_cell_length_b                   13.5219(9)
_cell_length_c                   17.3448(11)
_cell_measurement_reflns_used    4218
_cell_measurement_temperature    300(2)
_cell_measurement_theta_max      27.21
_cell_measurement_theta_min      2.43
_cell_volume                     912.56(10)
_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      300(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_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  0.034
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_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            14436
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.703
_diffrn_reflns_theta_min         1.551
_exptl_absorpt_coefficient_mu    8.822
_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    2.096
_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         0.343
_refine_diff_density_min         -0.43
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4243
_refine_ls_number_restraints     244
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0304
_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)+(0.0201P)²+0.1918P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0553
_refine_ls_wR_factor_ref         0.0623
_reflns_Friedel_coverage         0
_reflns_number_gt                2837
_reflns_number_total             4243
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc00836e2.cif
_cod_data_source_block           TBrB_BPE_300K
_cod_database_code               7123019
_shelx_estimated_absorpt_t_min   0.104
_shelx_estimated_absorpt_t_max   0.304
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 -0.28187(8) 0.71137(3) -0.02552(2) 0.05381(11) Uani 1 1 d . . . . .
Br2 Br 0.03403(9) 0.69045(3) 0.15401(2) 0.05892(11) Uani 1 1 d . . . . .
Br3 Br 0.53960(9) 0.21497(3) 0.44423(2) 0.05855(11) Uani 1 1 d . . . . .
Br4 Br 0.88463(8) 0.19927(3) 0.62308(2) 0.05572(11) Uani 1 1 d . . . . .
N1 N 0.5876(7) 0.4692(2) 0.23497(16) 0.0606(8) Uani 1 1 d . . . . .
C1 C 0.5735(8) 0.5473(3) 0.2960(2) 0.0550(9) Uani 1 1 d . . . . .
H1 H 0.472585 0.603583 0.286409 0.066 Uiso 1 1 calc R U . . .
C2 C 0.6978(7) 0.5509(2) 0.37238(18) 0.0462(8) Uani 1 1 d . . . . .
H2 H 0.677868 0.60774 0.412743 0.055 Uiso 1 1 calc R U . . .
C3 C 0.8533(7) 0.4685(2) 0.38836(17) 0.0398(7) Uani 1 1 d . . . . .
C4 C 0.8660(8) 0.3875(3) 0.32579(19) 0.0538(9) Uani 1 1 d . . . . .
H4 H 0.963702 0.329875 0.333463 0.065 Uiso 1 1 calc R U . . .
C5 C 0.7345(9) 0.3913(3) 0.2515(2) 0.0620(10) Uani 1 1 d . . . . .
H5 H 0.750139 0.335315 0.210154 0.074 Uiso 1 1 calc R U . . .
C6 C 1.0013(8) 0.4652(2) 0.46768(17) 0.0462(8) Uani 1 1 d . . . . .
H6 H 1.106918 0.407438 0.471685 0.055 Uiso 1 1 calc R U . . .
C7 C 0.1328(6) 0.4913(2) 0.07341(17) 0.0393(7) Uani 1 1 d . . . . .
H7 H 0.222194 0.485539 0.12284 0.047 Uiso 1 1 calc R U . . .
C8 C 0.0130(7) 0.5814(2) 0.06400(17) 0.0390(7) Uani 1 1 d . . . . .
C9 C -0.1190(6) 0.5897(2) -0.00936(17) 0.0365(7) Uani 1 1 d . . . . .
N2A N 0.8854(18) 0.0224(5) 0.2657(3) 0.0562(14) Uani 0.880(8) 1 d . U P A 1
C10A C 0.9845(17) 0.0986(5) 0.2346(3) 0.0561(15) Uani 0.880(8) 1 d . U P A 1
H10A H 1.121881 0.152267 0.266797 0.067 Uiso 0.880(8) 1 calc R U P A 1
C11A C 0.9004(15) 0.1050(4) 0.1580(3) 0.0510(13) Uani 0.880(8) 1 d . U P A 1
H11A H 0.980064 0.161439 0.139908 0.061 Uiso 0.880(8) 1 calc R U P A 1
C12A C 0.6966(14) 0.0271(4) 0.1079(3) 0.0427(12) Uani 0.880(8) 1 d D U P A 1
C13A C 0.5908(16) -0.0539(5) 0.1401(3) 0.0488(14) Uani 0.880(8) 1 d . U P A 1
H13A H 0.453059 -0.108797 0.109613 0.059 Uiso 0.880(8) 1 calc R U P A 1
C14A C 0.6926(18) -0.0519(5) 0.2178(3) 0.0540(13) Uani 0.880(8) 1 d . U P A 1
H14A H 0.619427 -0.107321 0.237916 0.065 Uiso 0.880(8) 1 calc R U P A 1
C15A C 0.6053(9) 0.0318(3) 0.0257(2) 0.0446(12) Uani 0.880(8) 1 d D U P A 1
H15A H 0.70853 0.085799 0.008196 0.053 Uiso 0.880(8) 1 calc R U P A 1
N2B N 0.928(13) 0.044(4) 0.2652(15) 0.051(5) Uani 0.120(8) 1 d G U P A 2
C10B C 1.019(11) 0.106(3) 0.215(2) 0.047(5) Uani 0.120(8) 1 d G U P A 2
H10B H 1.173447 0.16249 0.233077 0.057 Uiso 0.120(8) 1 calc R U P A 2
C11B C 0.881(12) 0.084(3) 0.137(2) 0.044(5) Uani 0.120(8) 1 d G U P A 2
H11B H 0.941671 0.125512 0.102908 0.053 Uiso 0.120(8) 1 calc R U P A 2
C12B C 0.650(11) -0.001(3) 0.1092(15) 0.042(4) Uani 0.120(8) 1 d DG U P A 2
C13B C 0.559(11) -0.063(3) 0.160(2) 0.040(4) Uani 0.120(8) 1 d G U P A 2
H13B H 0.405109 -0.119531 0.14129 0.048 Uiso 0.120(8) 1 calc R U P A 2
C14B C 0.698(14) -0.041(3) 0.238(2) 0.049(5) Uani 0.120(8) 1 d G U P A 2
H14B H 0.636881 -0.082555 0.27146 0.059 Uiso 0.120(8) 1 calc R U P A 2
C15B C 0.480(7) -0.025(2) 0.0274(13) 0.040(5) Uani 0.120(8) 1 d D U P A 2
H15B H 0.327307 -0.082531 0.014376 0.049 Uiso 0.120(8) 1 calc R U P A 2
C16 C 0.6453(6) -0.0069(2) 0.57271(16) 0.0379(7) Uani 1 1 d . . . . .
H16 H 0.744287 -0.011517 0.621576 0.046 Uiso 1 1 calc R U . . .
C17 C 0.6613(6) 0.0847(2) 0.55088(16) 0.0360(7) Uani 1 1 d . . . . .
C18 C 0.5175(6) 0.0920(2) 0.47794(16) 0.0349(7) 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 115.4(3) . .
N1 C1 C2 124.6(3) . .
N1 C1 H1 117.7 . .
C2 C1 H1 117.7 . .
C1 C2 C3 119.0(3) . .
C1 C2 H2 120.5 . .
C3 C2 H2 120.5 . .
C4 C3 C2 116.5(3) . .
C4 C3 C6 120.0(3) . .
C2 C3 C6 123.5(3) . .
C3 C4 C5 120.0(3) . .
C3 C4 H4 120 . .
C5 C4 H4 120 . .
N1 C5 C4 124.4(3) . .
N1 C5 H5 117.8 . .
C4 C5 H5 117.8 . .
C6 C6 C3 126.5(4) 2_766 .
C6 C6 H6 116.7 2_766 .
C3 C6 H6 116.7 . .
C9 C7 C8 119.5(3) 2_565 .
C9 C7 H7 120.2 2_565 .
C8 C7 H7 120.2 . .
C9 C8 C7 120.1(3) . .
C9 C8 Br2 121.8(2) . .
C7 C8 Br2 118.1(2) . .
C7 C9 C8 120.3(3) 2_565 .
C7 C9 Br1 117.9(2) 2_565 .
C8 C9 Br1 121.8(2) . .
C10A N2A C14A 115.3(4) . .
N2A C10A C11A 124.9(4) . .
N2A C10A H10A 117.6 . .
C11A C10A H10A 117.6 . .
C10A C11A C12A 119.7(4) . .
C10A C11A H11A 120.2 . .
C12A C11A H11A 120.2 . .
C11A C12A C13A 116.0(3) . .
C11A C12A C15A 120.7(4) . .
C13A C12A C15A 123.3(4) . .
C14A C13A C12A 119.1(4) . .
C14A C13A H13A 120.5 . .
C12A C13A H13A 120.5 . .
N2A C14A C13A 125.0(4) . .
N2A C14A H14A 117.5 . .
C13A C14A H14A 117.5 . .
C15A C15A C12A 127.0(6) 2_655 .
C15A C15A H15A 116.5 2_655 .
C12A C15A H15A 116.5 . .
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 118(3) . .
C11B C12B C15B 122(3) . .
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 127(4) 2_655 .
C15B C15B H15B 116.3 2_655 .
C12B C15B H15B 116.3 . .
C17 C16 C18 119.7(2) . 2_656
C17 C16 H16 120.1 . .
C18 C16 H16 120.1 2_656 .
C16 C17 C18 120.5(2) . .
C16 C17 Br4 118.0(2) . .
C18 C17 Br4 121.5(2) . .
C16 C18 C17 119.7(3) 2_656 .
C16 C18 Br3 118.0(2) 2_656 .
C17 C18 Br3 122.3(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C9 1.885(3) .
Br2 C8 1.888(3) .
Br3 C18 1.879(3) .
Br4 C17 1.889(3) .
N1 C5 1.321(4) .
N1 C1 1.327(4) .
C1 C2 1.376(4) .
C1 H1 0.93 .
C2 C3 1.389(4) .
C2 H2 0.93 .
C3 C4 1.366(4) .
C3 C6 1.475(4) .
C4 C5 1.374(4) .
C4 H4 0.93 .
C5 H5 0.93 .
C6 C6 1.295(6) 2_766
C6 H6 0.93 .
C7 C9 1.371(4) 2_565
C7 C8 1.382(4) .
C7 H7 0.93 .
C8 C9 1.379(4) .
N2A C10A 1.313(6) .
N2A C14A 1.317(5) .
C10A C11A 1.373(6) .
C10A H10A 0.93 .
C11A C12A 1.382(5) .
C11A H11A 0.93 .
C12A C13A 1.386(5) .
C12A C15A 1.467(5) .
C13A C14A 1.378(5) .
C13A H13A 0.93 .
C14A H14A 0.93 .
C15A C15A 1.306(7) 2_655
C15A H15A 0.93 .
N2B C10B 1.39 .
N2B C14B 1.39 .
C10B C11B 1.39 .
C10B H10B 0.93 .
C11B C12B 1.39 .
C11B H11B 0.93 .
C12B C13B 1.39 .
C12B C15B 1.49(2) .
C13B C14B 1.39 .
C13B H13B 0.93 .
C14B H14B 0.93 .
C15B C15B 1.29(3) 2_655
C15B H15B 0.93 .
C16 C17 1.371(4) .
C16 C18 1.375(4) 2_656
C16 H16 0.93 .
C17 C18 1.384(4) .
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 0.93 2.42 3.330(4) 165.3 .
C16 H16 N2A 0.93 2.42 3.332(6) 167.4 2_756
C16 H16 N2B 0.93 2.43 3.35(3) 169.4 2_756
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139189548
