#------------------------------------------------------------------------------
#$Date: 2019-02-22 00:06:46 +0100 (vie 22 de feb de 2019) $
#$Revision: 213767 $
#$URL: svn://www.crystallography.net/cod/cif/7/12/30/7123025.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_7123025
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             2018-10-31T15:21:35-00:00
_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                75.801(10)
_cell_angle_beta                 84.980(11)
_cell_angle_gamma                78.541(11)
_cell_formula_units_Z            1
_cell_length_a                   3.9240(8)
_cell_length_b                   9.667(2)
_cell_length_c                   12.375(3)
_cell_measurement_reflns_used    3186
_cell_measurement_temperature    189(2)
_cell_measurement_theta_max      27.45
_cell_measurement_theta_min      2.45
_cell_volume                     445.64(17)
_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      189(2)
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.96
_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  0.0879
_diffrn_reflns_av_unetI/netI     0.0585
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.96
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6392
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.96
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.552
_diffrn_reflns_theta_min         1.699
_exptl_absorpt_coefficient_mu    9.033
_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    2.146
_exptl_crystal_description       rod
_exptl_crystal_F_000             274
_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         2.024
_refine_diff_density_min         -1.164
_refine_diff_density_rms         0.191
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     109
_refine_ls_number_reflns         1972
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.001
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0451
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0728P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1148
_refine_ls_wR_factor_ref         0.1181
_reflns_Friedel_coverage         0
_reflns_number_gt                1587
_reflns_number_total             1972
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9cc00836e2.cif
_cod_data_source_block           TBrB_BPE_190K
_cod_original_cell_volume        445.65(17)
_cod_database_code               7123025
_shelx_estimated_absorpt_t_min   0.101
_shelx_estimated_absorpt_t_max   0.298
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
Br1 Br 0.57426(13) 0.34147(4) 0.44163(4) 0.03122(18) Uani 1 1 d . .
Br2 Br 0.34208(13) 0.18909(5) 0.24656(3) 0.03165(18) Uani 1 1 d . .
N1 N 0.0858(12) 0.8088(4) 0.2335(3) 0.0341(9) Uani 1 1 d . .
C1 C 0.1816(14) 0.8538(5) 0.1269(4) 0.0356(12) Uani 1 1 d . .
H1 H 0.257603 0.944396 0.104308 0.043 Uiso 1 1 calc R U
C2 C 0.1768(13) 0.7763(5) 0.0470(4) 0.0300(10) Uani 1 1 d . .
H2 H 0.244454 0.814318 -0.028387 0.036 Uiso 1 1 calc R U
C3 C 0.0723(11) 0.6424(4) 0.0777(3) 0.0222(9) Uani 1 1 d . .
C4 C -0.0281(13) 0.5950(5) 0.1893(4) 0.0289(10) Uani 1 1 d . .
H4 H -0.105482 0.505 0.214925 0.035 Uiso 1 1 calc R U
C5 C -0.0132(13) 0.6812(5) 0.2622(4) 0.0334(11) Uani 1 1 d . .
H5 H -0.078597 0.646317 0.338277 0.04 Uiso 1 1 calc R U
C6 C 0.0685(12) 0.5589(4) -0.0068(4) 0.0249(9) Uani 1 1 d . .
H6 H 0.174576 0.592946 -0.07785 0.03 Uiso 1 1 calc R U
C7 C 0.5981(11) 0.0625(4) 0.5801(3) 0.0220(9) Uani 1 1 d . .
H7 H 0.666595 0.105078 0.634264 0.026 Uiso 1 1 calc R U
C8 C 0.5294(11) 0.1442(4) 0.4731(3) 0.0224(9) Uani 1 1 d . .
C9 C 0.4341(11) 0.0821(4) 0.3928(3) 0.0201(8) 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'
N N 0.0061 0.0033 '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'
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 116.4(4) .
N1 C1 C2 123.7(4) .
N1 C1 H1 118.2 .
C2 C1 H1 118.2 .
C1 C2 C3 119.6(4) .
C1 C2 H2 120.2 .
C3 C2 H2 120.2 .
C2 C3 C4 116.8(4) .
C2 C3 C6 119.8(4) .
C4 C3 C6 123.3(4) .
C5 C4 C3 118.8(4) .
C5 C4 H4 120.6 .
C3 C4 H4 120.6 .
N1 C5 C4 124.6(4) .
N1 C5 H5 117.7 .
C4 C5 H5 117.7 .
C6 C6 C3 126.2(5) 2_565
C6 C6 H6 116.9 2_565
C3 C6 H6 116.9 .
C9 C7 C8 119.2(4) 2_656
C9 C7 H7 120.4 2_656
C8 C7 H7 120.4 .
C7 C8 C9 120.7(4) .
C7 C8 Br1 117.2(3) .
C9 C8 Br1 122.1(3) .
C7 C9 C8 120.0(4) 2_656
C7 C9 Br2 118.0(3) 2_656
C8 C9 Br2 122.0(3) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Br1 C8 1.891(4) .
Br2 C9 1.877(4) .
N1 C5 1.323(6) .
N1 C1 1.330(6) .
C1 C2 1.383(6) .
C1 H1 0.95 .
C2 C3 1.390(6) .
C2 H2 0.95 .
C3 C4 1.393(6) .
C3 C6 1.471(5) .
C4 C5 1.381(6) .
C4 H4 0.95 .
C5 H5 0.95 .
C6 C6 1.323(8) 2_565
C6 H6 0.95 .
C7 C9 1.383(5) 2_656
C7 C8 1.384(6) .
C7 H7 0.95 .
C8 C9 1.391(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 2.36 3.306(5) 172 2_666
