#------------------------------------------------------------------------------
#$Date: 2019-02-22 01:06:46 +0200 (Fri, 22 Feb 2019) $
#$Revision: 213767 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/30/7123023.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_7123023
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             2018-10-31T14:43:56-00:00
_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                102.783(2)
_cell_angle_beta                 93.452(2)
_cell_angle_gamma                94.301(2)
_cell_formula_units_Z            2
_cell_length_a                   4.0022(2)
_cell_length_b                   13.5102(6)
_cell_length_c                   17.3261(8)
_cell_measurement_reflns_used    3186
_cell_measurement_temperature    269(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.45
_cell_volume                     908.19(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      269(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  0.0337
_diffrn_reflns_av_unetI/netI     0.036
_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            14247
_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         27.553
_diffrn_reflns_theta_min         1.552
_exptl_absorpt_coefficient_mu    8.865
_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    2.106
_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         0.305
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.072
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4168
_refine_ls_number_restraints     244
_refine_ls_restrained_S_all      1
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0276
_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)+(0.0199P)²+0.1391P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0531
_refine_ls_wR_factor_ref         0.0595
_reflns_Friedel_coverage         0
_reflns_number_gt                2900
_reflns_number_total             4168
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc00836e2.cif
_cod_data_source_block           TBrB_BPE_270K
_cod_database_code               7123023
_shelx_estimated_absorpt_t_min   0.104
_shelx_estimated_absorpt_t_max   0.303
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 -0.28241(8) 0.71159(2) -0.02548(2) 0.04900(10) Uani 1 1 d . . . . .
Br2 Br 0.03529(8) 0.69080(3) 0.15404(2) 0.05351(10) Uani 1 1 d . . . . .
Br3 Br 0.54044(8) 0.21517(2) 0.44417(2) 0.05338(10) Uani 1 1 d . . . . .
Br4 Br 0.88504(8) 0.19943(2) 0.62315(2) 0.05067(10) Uani 1 1 d . . . . .
N1 N 0.5891(7) 0.4695(2) 0.23492(15) 0.0549(7) Uani 1 1 d . . . . .
C1 C 0.5734(8) 0.5476(3) 0.29624(18) 0.0506(8) Uani 1 1 d . . . . .
H1 H 0.470613 0.603782 0.286854 0.061 Uiso 1 1 calc R U . . .
C2 C 0.6986(7) 0.5512(2) 0.37256(17) 0.0422(7) Uani 1 1 d . . . . .
H2 H 0.679735 0.60806 0.41305 0.051 Uiso 1 1 calc R U . . .
C3 C 0.8534(6) 0.4685(2) 0.38807(16) 0.0358(7) Uani 1 1 d . . . . .
C4 C 0.8675(8) 0.3871(2) 0.32538(17) 0.0482(8) Uani 1 1 d . . . . .
H4 H 0.96551 0.32943 0.33315 0.058 Uiso 1 1 calc R U . . .
C5 C 0.7363(8) 0.3910(3) 0.25096(18) 0.0547(9) Uani 1 1 d . . . . .
H5 H 0.751944 0.335085 0.209399 0.066 Uiso 1 1 calc R U . . .
C6 C 1.0013(7) 0.4647(2) 0.46732(16) 0.0402(7) Uani 1 1 d . . . . .
H6 H 1.106117 0.406657 0.471272 0.048 Uiso 1 1 calc R U . . .
C7 C 0.1331(6) 0.4917(2) 0.07344(16) 0.0361(7) Uani 1 1 d . . . . .
H7 H 0.223515 0.485962 0.122812 0.043 Uiso 1 1 calc R U . . .
C8 C 0.0132(6) 0.5817(2) 0.06437(16) 0.0350(6) Uani 1 1 d . . . . .
C9 C -0.1187(6) 0.5896(2) -0.00934(17) 0.0338(6) Uani 1 1 d . . . . .
N2A N 0.8872(18) 0.0222(4) 0.2655(3) 0.0518(13) Uani 0.908(8) 1 d . U P A 1
C10A C 0.9879(18) 0.0979(5) 0.2341(3) 0.0535(15) Uani 0.908(8) 1 d . U P A 1
H10A H 1.128049 0.151247 0.26599 0.064 Uiso 0.908(8) 1 calc R U P A 1
C11A C 0.9016(18) 0.1044(4) 0.1575(3) 0.0481(13) Uani 0.908(8) 1 d . U P A 1
H11A H 0.980649 0.160785 0.139157 0.058 Uiso 0.908(8) 1 calc R U P A 1
C12A C 0.6972(16) 0.0265(4) 0.1082(2) 0.0405(13) Uani 0.908(8) 1 d D U P A 1
C13A C 0.5896(17) -0.0543(5) 0.1402(3) 0.0458(13) Uani 0.908(8) 1 d . U P A 1
H13A H 0.450461 -0.109093 0.109852 0.055 Uiso 0.908(8) 1 calc R U P A 1
C14A C 0.6929(19) -0.0520(4) 0.2181(3) 0.0506(13) Uani 0.908(8) 1 d . U P A 1
H14A H 0.619454 -0.107217 0.238594 0.061 Uiso 0.908(8) 1 calc R U P A 1
C15A C 0.6058(8) 0.0316(3) 0.0251(2) 0.0418(11) Uani 0.908(8) 1 d D U P A 1
H15A H 0.71016 0.08531 0.007264 0.05 Uiso 0.908(8) 1 calc R U P A 1
N2B N 0.91(2) 0.047(5) 0.268(2) 0.048(5) Uani 0.092(8) 1 d G U P A 2
C10B C 1.007(17) 0.112(4) 0.220(3) 0.045(5) Uani 0.092(8) 1 d G U P A 2
H10B H 1.154944 0.169002 0.240818 0.055 Uiso 0.092(8) 1 calc R U P A 2
C11B C 0.888(19) 0.090(4) 0.140(3) 0.041(5) Uani 0.092(8) 1 d G U P A 2
H11B H 0.955431 0.133537 0.108186 0.049 Uiso 0.092(8) 1 calc R U P A 2
C12B C 0.667(18) 0.004(5) 0.109(2) 0.041(4) Uani 0.092(8) 1 d DG U P A 2
C13B C 0.566(16) -0.060(4) 0.157(3) 0.042(5) Uani 0.092(8) 1 d G U P A 2
H13B H 0.418347 -0.117835 0.13615 0.051 Uiso 0.092(8) 1 calc R U P A 2
C14B C 0.69(2) -0.039(4) 0.237(3) 0.044(5) Uani 0.092(8) 1 d G U P A 2
H14B H 0.617858 -0.082373 0.268782 0.053 Uiso 0.092(8) 1 calc R U P A 2
C15B C 0.492(9) -0.025(3) 0.0276(16) 0.040(5) Uani 0.092(8) 1 d D U P A 2
H15B H 0.357165 -0.086346 0.015319 0.048 Uiso 0.092(8) 1 calc R U P A 2
C16 C 0.6457(6) -0.0071(2) 0.57291(15) 0.0337(6) Uani 1 1 d . . . . .
H16 H 0.743474 -0.011768 0.621892 0.04 Uiso 1 1 calc R U . . .
C17 C 0.6630(6) 0.0850(2) 0.55070(15) 0.0318(6) Uani 1 1 d . . . . .
C18 C 0.5175(6) 0.0919(2) 0.47803(15) 0.0316(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 115.7(3) .
N1 C1 C2 124.6(3) .
N1 C1 H1 117.7 .
C2 C1 H1 117.7 .
C1 C2 C3 118.8(3) .
C1 C2 H2 120.6 .
C3 C2 H2 120.6 .
C4 C3 C2 117.1(2) .
C4 C3 C6 119.5(3) .
C2 C3 C6 123.5(3) .
C3 C4 C5 119.8(3) .
C3 C4 H4 120.1 .
C5 C4 H4 120.1 .
N1 C5 C4 124.0(3) .
N1 C5 H5 118 .
C4 C5 H5 118 .
C6 C6 C3 126.1(4) 2_766
C6 C6 H6 116.9 2_766
C3 C6 H6 116.9 .
C9 C7 C8 119.8(2) 2_565
C9 C7 H7 120.1 2_565
C8 C7 H7 120.1 .
C7 C8 C9 119.6(2) .
C7 C8 Br2 118.3(2) .
C9 C8 Br2 122.1(2) .
C7 C9 C8 120.6(2) 2_565
C7 C9 Br1 118.0(2) 2_565
C8 C9 Br1 121.5(2) .
C10A N2A C14A 115.6(3) .
N2A C10A C11A 124.8(4) .
N2A C10A H10A 117.6 .
C11A C10A H10A 117.6 .
C10A C11A C12A 119.3(4) .
C10A C11A H11A 120.3 .
C12A C11A H11A 120.3 .
C11A C12A C13A 116.7(3) .
C11A C12A C15A 120.0(4) .
C13A C12A C15A 123.3(4) .
C14A C13A C12A 118.6(3) .
C14A C13A H13A 120.7 .
C12A C13A H13A 120.7 .
N2A C14A C13A 124.9(4) .
N2A C14A H14A 117.5 .
C13A C14A H14A 117.5 .
C15A C15A C12A 126.1(5) 2_655
C15A C15A H15A 116.9 2_655
C12A C15A H15A 116.9 .
C10B N2B C14B 120 .
C11B C10B N2B 120 .
C11B C10B H10B 120 .
N2B C10B H10B 120 .
C10B C11B C12B 120 .
C10B C11B H11B 120 .
C12B C11B H11B 120 .
C11B C12B C13B 120 .
C11B C12B C15B 127(4) .
C13B C12B C15B 113(4) .
C14B C13B C12B 120 .
C14B C13B H13B 120 .
C12B C13B H13B 120 .
C13B C14B N2B 120 .
C13B C14B H14B 120 .
N2B C14B H14B 120 .
C15B C15B C12B 127(5) 2_655
C15B C15B H15B 116.3 2_655
C12B C15B H15B 116.3 .
C18 C16 C17 119.4(2) 2_656
C18 C16 H16 120.3 2_656
C17 C16 H16 120.3 .
C16 C17 C18 120.3(2) .
C16 C17 Br4 117.79(19) .
C18 C17 Br4 121.9(2) .
C16 C18 C17 120.3(2) 2_656
C16 C18 Br3 117.70(19) 2_656
C17 C18 Br3 122.0(2) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C9 1.889(3) .
Br2 C8 1.882(3) .
Br3 C18 1.882(3) .
Br4 C17 1.886(2) .
N1 C5 1.325(4) .
N1 C1 1.330(4) .
C1 C2 1.375(4) .
C1 H1 0.93 .
C2 C3 1.385(4) .
C2 H2 0.93 .
C3 C4 1.372(4) .
C3 C6 1.475(4) .
C4 C5 1.376(4) .
C4 H4 0.93 .
C5 H5 0.93 .
C6 C6 1.311(6) 2_766
C6 H6 0.93 .
C7 C9 1.373(4) 2_565
C7 C8 1.378(4) .
C7 H7 0.93 .
C8 C9 1.381(3) .
N2A C10A 1.310(5) .
N2A C14A 1.313(5) .
C10A C11A 1.374(5) .
C10A H10A 0.93 .
C11A C12A 1.376(5) .
C11A H11A 0.93 .
C12A C13A 1.383(5) .
C12A C15A 1.483(5) .
C13A C14A 1.381(5) .
C13A H13A 0.93 .
C14A H14A 0.93 .
C15A C15A 1.295(6) 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 C18 1.374(3) 2_656
C16 C17 1.380(4) .
C16 H16 0.93 .
C17 C18 1.380(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 0.93 2.42 3.329(3) 165.6 .
C16 H16 N2A 0.93 2.41 3.325(5) 167.1 2_756
C16 H16 N2B 0.93 2.45 3.36(4) 166.6 2_756
