# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TBrB_BPE_300K
_database_code_depnum_ccdc_archive 'CCDC 1889834'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2019-01-09 deposited with the CCDC.	2019-02-21 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT250_TBrB_BPE_300K       
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        3.2 Note  
RESPONSE: Due to the disorder about the 1,2-bis(4-pyridyl)ethylene molecule. 
;
_vrf_PLAT905_TBrB_BPE_300K       
;
PROBLEM: Negative K value in the Analysis of Variance ...     -0.362 Report
RESPONSE: Due to a slight issue with the absorption correction.
;
# end Validation Reply Form

_audit_creation_date             2018-10-31T14:43:28-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C18 H12 Br4 N2'
_chemical_formula_weight         575.94

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.0143(2)
_cell_length_b                   13.5219(9)
_cell_length_c                   17.3448(11)
_cell_angle_alpha                102.786(3)
_cell_angle_beta                 93.568(3)
_cell_angle_gamma                94.296(3)
_cell_volume                     912.56(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    4218
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      27.21

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.468
_exptl_crystal_size_mid          0.202
_exptl_crystal_size_min          0.177
_exptl_crystal_density_diffrn    2.096
_exptl_crystal_F_000             548

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    8.822
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_correction_T_min  0.5748
_shelx_estimated_absorpt_T_min   0.104
_shelx_estimated_absorpt_T_max   0.304

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_R_equivalents  0.034
_diffrn_reflns_av_unetI/netI     0.0371
_diffrn_reflns_number            14436
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.551
_diffrn_reflns_theta_max         27.703
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_reflns_Friedel_coverage         0
_reflns_number_total             4243
_reflns_number_gt                2837
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0201P)²+0.1918P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4243
_refine_ls_number_parameters     271
_refine_ls_number_restraints     244
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0623
_refine_ls_wR_factor_gt          0.0553
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.43
_refine_diff_density_rms         0.072

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
The 1,2-bis(4-pyridyl)ethylene molecule was disordered about two positions, A 
and B.  The site occupancies of the two sites were allowed to free refine to 
a constrained total of 1.  The site occupancies for sites A and B refined to 
0.88 and 0.12, respectively.  To help restrain the disordered sites, SIMU, 
DLEU, and free variable DFIX commands for C-C and C-N bond distances were 
applied.  
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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_
_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 . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_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
_geom_angle_publ_flag
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_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

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TBrB_BPE_210K
_database_code_depnum_ccdc_archive 'CCDC 1889838'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2019-01-09 deposited with the CCDC.	2019-02-21 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT250_TBrB_BPE_210K       
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.3 Note  
RESPONSE: The 1,2-bis(4-pyridyl)ethylene molecule rotates very slightly about 
          C3 atom site.  Attempts to model split positions similar to the 
          structure at higher temperatures did not improve the model.
;
_vrf_PLAT911_TBrB_BPE_210K       
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          2 Report
RESPONSE: These reflections were not collected using only omega scans.
;
# end Validation Reply Form

_audit_creation_date             2018-10-31T15:21:15-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C18 H12 Br4 N2'
_chemical_formula_weight         575.94

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.9561(17)
_cell_length_b                   9.702(4)
_cell_length_c                   12.444(5)
_cell_angle_alpha                75.878(7)
_cell_angle_beta                 84.947(5)
_cell_angle_gamma                78.556(5)
_cell_volume                     453.6(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    210(2)
_cell_measurement_reflns_used    3255
_cell_measurement_theta_min      2.44
_cell_measurement_theta_max      27.22

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       chunk
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.33
_exptl_crystal_density_diffrn    2.108
_exptl_crystal_F_000             274

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    8.874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.2255
_shelx_estimated_absorpt_T_min   0.1
_shelx_estimated_absorpt_T_max   0.158

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      210(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_av_unetI/netI     0.0515
_diffrn_reflns_number            7547
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.689
_diffrn_reflns_theta_max         27.241
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_Friedel_coverage         0
_reflns_number_total             2017
_reflns_number_gt                1633
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0421P)²+0.2799P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2017
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.049
_refine_ls_R_factor_gt           0.0346
_refine_ls_wR_factor_ref         0.0922
_refine_ls_wR_factor_gt          0.0861
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.687
_refine_diff_density_min         -0.876
_refine_diff_density_rms         0.134

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
The reflection 0 1 0 was also omitted due to interference by the beamstop. 
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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_
_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 0.57492(11) 0.34117(4) 0.44164(3) 0.02968(15) Uani 1 1 d . . . . .
Br2 Br 0.34450(11) 0.18865(5) 0.24662(3) 0.02997(15) Uani 1 1 d . . . . .
N1 N 0.0886(10) 0.8082(4) 0.2336(3) 0.0330(9) Uani 1 1 d . . . . .
C1 C 0.1842(12) 0.8519(5) 0.1270(4) 0.0343(11) Uani 1 1 d . . . . .
H1 H 0.262751 0.940323 0.104926 0.041 Uiso 1 1 calc R U . . .
C2 C 0.1755(11) 0.7761(5) 0.0470(3) 0.0266(9) Uani 1 1 d . . . . .
H2 H 0.238377 0.814316 -0.027321 0.032 Uiso 1 1 calc R U . . .
C3 C 0.0723(10) 0.6420(4) 0.0779(3) 0.0198(8) Uani 1 1 d . . . . .
C4 C -0.0263(11) 0.5947(5) 0.1887(3) 0.0255(9) Uani 1 1 d . . . . .
H4 H -0.102707 0.5061 0.213563 0.031 Uiso 1 1 calc R U . . .
C5 C -0.0105(12) 0.6801(5) 0.2625(3) 0.0316(10) Uani 1 1 d . . . . .
H5 H -0.07377 0.645391 0.337375 0.038 Uiso 1 1 calc R U . . .
C6 C 0.0669(10) 0.5592(4) -0.0071(3) 0.0217(8) Uani 1 1 d . . . . .
H6 H 0.167271 0.59368 -0.077424 0.026 Uiso 1 1 calc R U . . .
C7 C 0.5963(9) 0.0623(4) 0.5796(3) 0.0205(8) Uani 1 1 d . . . . .
H7 H 0.663023 0.104225 0.633026 0.025 Uiso 1 1 calc R U . . .
C8 C 0.5307(10) 0.1438(4) 0.4734(3) 0.0192(8) Uani 1 1 d . . . . .
C9 C 0.4368(10) 0.0812(4) 0.3935(3) 0.0189(8) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C8 1.899(4) . ?
Br2 C9 1.896(4) . ?
N1 C5 1.333(6) . ?
N1 C1 1.336(6) . ?
C1 C2 1.381(5) . ?
C1 H1 0.94 . ?
C2 C3 1.395(6) . ?
C2 H2 0.94 . ?
C3 C4 1.390(6) . ?
C3 C6 1.479(5) . ?
C4 C5 1.391(5) . ?
C4 H4 0.94 . ?
C5 H5 0.94 . ?
C6 C6 1.326(8) 2_565 ?
C6 H6 0.94 . ?
C7 C9 1.380(5) 2_656 ?
C7 C8 1.380(5) . ?
C7 H7 0.94 . ?
C8 C9 1.395(5) . ?

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
_geom_angle_publ_flag
C5 N1 C1 116.0(4) . . ?
N1 C1 C2 124.4(4) . . ?
N1 C1 H1 117.8 . . ?
C2 C1 H1 117.8 . . ?
C1 C2 C3 119.2(4) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C4 C3 C2 117.0(3) . . ?
C4 C3 C6 123.6(4) . . ?
C2 C3 C6 119.5(4) . . ?
C3 C4 C5 119.3(4) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 124.1(4) . . ?
N1 C5 H5 118 . . ?
C4 C5 H5 118 . . ?
C6 C6 C3 125.8(5) 2_565 . ?
C6 C6 H6 117.1 2_565 . ?
C3 C6 H6 117.1 . . ?
C9 C7 C8 119.5(3) 2_656 . ?
C9 C7 H7 120.3 2_656 . ?
C8 C7 H7 120.3 . . ?
C7 C8 C9 120.4(4) . . ?
C7 C8 Br1 117.6(3) . . ?
C9 C8 Br1 122.0(3) . . ?
C7 C9 C8 120.1(3) 2_656 . ?
C7 C9 Br2 118.0(3) 2_656 . ?
C8 C9 Br2 121.9(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 2.4 3.331(5) 172 2_666

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TBrB_BPE_250K
_database_code_depnum_ccdc_archive 'CCDC 1889836'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2019-01-09 deposited with the CCDC.	2019-02-21 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT250_TBrB_BPE_250K       
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.9 Note  
RESPONSE: Due to the disorder about the 1,2-bis(4-pyridyl)ethylene molecule.
;
# end Validation Reply Form

_audit_creation_date             2018-10-31T15:20:17-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C18 H12 Br4 N2'
_chemical_formula_weight         575.94

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.9924(2)
_cell_length_b                   13.5015(6)
_cell_length_c                   17.3091(8)
_cell_angle_alpha                102.795(2)
_cell_angle_beta                 93.323(2)
_cell_angle_gamma                94.316(2)
_cell_volume                     904.59(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    249(2)
_cell_measurement_reflns_used    4393
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      26.81

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.468
_exptl_crystal_size_mid          0.202
_exptl_crystal_size_min          0.177
_exptl_crystal_density_diffrn    2.114
_exptl_crystal_F_000             548

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    8.9
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_correction_T_min  0.5748
_shelx_estimated_absorpt_T_min   0.103
_shelx_estimated_absorpt_T_max   0.302

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      249(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_R_equivalents  0.0335
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_number            14191
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.553
_diffrn_reflns_theta_max         27.561
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_reflns_Friedel_coverage         0
_reflns_number_total             4155
_reflns_number_gt                3022
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0179P)²+0.2285P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4155
_refine_ls_number_parameters     271
_refine_ls_number_restraints     244
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0275
_refine_ls_wR_factor_ref         0.0581
_refine_ls_wR_factor_gt          0.0523
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.074

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
The 1,2-bis(4-pyridyl)ethylene molecule was disordered about two positions, A 
and B.  The site occupancies of the two sites were allowed to free refine to 
a constrained total of 1.  The site occupancies for sites A and B refined to 
0.93 and 0.07, respectively.  To help restrain the disordered sites, SIMU, 
DLEU, and free variable DFIX commands for C-C and C-N bond distances were 
applied. The reflection 0 0 1 was also omitted. 
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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_
_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 . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_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
_geom_angle_publ_flag
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_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

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TBrB_BPE_100K
_database_code_depnum_ccdc_archive 'CCDC 1889840'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2019-01-09 deposited with the CCDC.	2019-02-21 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT906_TBrB_BPE_100K       
;
PROBLEM: Large K Value in the Analysis of Variance ......      2.409 Check 
RESPONSE: Due to issues with an intermittently faulty quandrant on the detector.
;
_vrf_PLAT911_TBrB_BPE_100K       
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600         10 Report
RESPONSE: These reflections were not collected using only omega scans.
;
_vrf_PLAT977_TBrB_BPE_100K       
;
PROBLEM: Check Negative Difference Density on H14A             -0.38 eA-3  
RESPONSE: These positions were determined by geometric constraints.
;
_vrf_PLAT978_TBrB_BPE_100K       
;
PROBLEM: Number C-C Bonds with Positive Residual Density.          0 Info  
RESPONSE: The remaining electron density was centered mostly around the 
          bromine atoms.
;
# end Validation Reply Form

_audit_creation_date             2018-10-31T15:21:59-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C18 H12 Br4 N2'
_chemical_formula_weight         575.94

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.9431(6)
_cell_length_b                   13.4500(19)
_cell_length_c                   17.231(2)
_cell_angle_alpha                102.747(2)
_cell_angle_beta                 92.460(2)
_cell_angle_gamma                94.329(2)
_cell_volume                     887.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3778
_cell_measurement_theta_min      2.43
_cell_measurement_theta_max      26.86

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       chunk
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.375
_exptl_crystal_size_min          0.21
_exptl_crystal_density_diffrn    2.156
_exptl_crystal_F_000             548

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    9.075
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.3247
_shelx_estimated_absorpt_T_min   0.097
_shelx_estimated_absorpt_T_max   0.252

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0496
_diffrn_reflns_av_unetI/netI     0.0615
_diffrn_reflns_number            12565
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.558
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_reflns_Friedel_coverage         0
_reflns_number_total             3590
_reflns_number_gt                2714
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0341P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3590
_refine_ls_number_parameters     271
_refine_ls_number_restraints     244
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.036
_refine_ls_wR_factor_ref         0.0869
_refine_ls_wR_factor_gt          0.0796
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      0.999
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.613
_refine_diff_density_min         -0.857
_refine_diff_density_rms         0.152

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
The 1,2-bis(4-pyridyl)ethylene molecule was disordered about two positions, A 
and B.  The site occupancies of the two sites were allowed to free refine to 
a constrained total of 1.  The site occupancies for sites A and B refined to 
0.88 and 0.12, respectively.  To help restrain the disordered sites, SIMU, 
DLEU, and free variable DFIX commands for C-C and C-N bond distances were 
applied. The reflection 0 0 1 was omitted due to interference by the beamstop. 
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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_
_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 . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_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
_geom_angle_publ_flag
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_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



# END of CIF
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TBrB_BPE_270K
_database_code_depnum_ccdc_archive 'CCDC 1889835'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2019-01-09 deposited with the CCDC.	2019-02-21 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT250_TBrB_BPE_270K       
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.5 Note  
RESPONSE: Due to the disorder about the 1,2-bis(4-pyridyl)ethylene molecule.
;
# end Validation Reply Form

_audit_creation_date             2018-10-31T14:43:56-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C18 H12 Br4 N2'
_chemical_formula_weight         575.94

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.0022(2)
_cell_length_b                   13.5102(6)
_cell_length_c                   17.3261(8)
_cell_angle_alpha                102.783(2)
_cell_angle_beta                 93.452(2)
_cell_angle_gamma                94.301(2)
_cell_volume                     908.19(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    269(2)
_cell_measurement_reflns_used    3186
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      27.45

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.468
_exptl_crystal_size_mid          0.202
_exptl_crystal_size_min          0.177
_exptl_crystal_density_diffrn    2.106
_exptl_crystal_F_000             548

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    8.865
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_correction_T_min  0.5748
_shelx_estimated_absorpt_T_min   0.104
_shelx_estimated_absorpt_T_max   0.303

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      269(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_R_equivalents  0.0337
_diffrn_reflns_av_unetI/netI     0.036
_diffrn_reflns_number            14247
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.552
_diffrn_reflns_theta_max         27.553
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_reflns_Friedel_coverage         0
_reflns_number_total             4168
_reflns_number_gt                2900
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0199P)²+0.1391P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4168
_refine_ls_number_parameters     271
_refine_ls_number_restraints     244
_refine_ls_R_factor_all          0.0528
_refine_ls_R_factor_gt           0.0276
_refine_ls_wR_factor_ref         0.0595
_refine_ls_wR_factor_gt          0.0531
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.305
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.072

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
The 1,2-bis(4-pyridyl)ethylene molecule was disordered about two positions, A 
and B. The site occupancies of the two sites were allowed to free refine to 
a constrained total of 1. The site occupancies for sites A and B refined to 
0.91 and 0.09, respectively. To help restrain the disordered sites, SIMU, 
DLEU, and free variable DFIX commands for C-C and C-N bond distances were 
applied. The reflection 0 0 1 was also omitted. 
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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_
_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 . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_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
_geom_angle_publ_flag
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_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

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TBrB_BPE_230K
_database_code_depnum_ccdc_archive 'CCDC 1889837'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2019-01-09 deposited with the CCDC.	2019-02-21 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT250_TBrB_BPE_230K       
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.1 Note  
RESPONSE: Due to the disorder about the 1,2-bis(4-pyridyl)ethylene molecule.
;
# end Validation Reply Form

_audit_creation_date             2018-10-31T15:20:46-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C18 H12 Br4 N2'
_chemical_formula_weight         575.94

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.9826(2)
_cell_length_b                   13.4966(7)
_cell_length_c                   17.2973(8)
_cell_angle_alpha                102.810(2)
_cell_angle_beta                 93.204(2)
_cell_angle_gamma                94.321(2)
_cell_volume                     901.51(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    229(2)
_cell_measurement_reflns_used    4641
_cell_measurement_theta_min      2.42
_cell_measurement_theta_max      27.32

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.468
_exptl_crystal_size_mid          0.202
_exptl_crystal_size_min          0.177
_exptl_crystal_density_diffrn    2.122
_exptl_crystal_F_000             548

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    8.93
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_correction_T_min  0.5748
_shelx_estimated_absorpt_T_min   0.103
_shelx_estimated_absorpt_T_max   0.301

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      229(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_R_equivalents  0.0837
_diffrn_reflns_av_unetI/netI     0.0646
_diffrn_reflns_number            14172
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.554
_diffrn_reflns_theta_max         27.575
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.99
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.99
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.99
_reflns_Friedel_coverage         0
_reflns_number_total             4140
_reflns_number_gt                2762
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0461P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4140
_refine_ls_number_parameters     271
_refine_ls_number_restraints     244
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.0994
_refine_ls_wR_factor_gt          0.0943
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_restrained_S_all      0.908
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.225
_refine_diff_density_min         -1.13
_refine_diff_density_rms         0.146

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#

_refine_special_details          
;
The 1,2-bis(4-pyridyl)ethylene molecule was disordered about two positions, A 
and B.  The site occupancies of the two sites were allowed to free refine to 
a constrained total of 1.  The site occupancies for sites A and B refined to 
0.95 and 0.05, respectively.  To help restrain the disordered sites, SIMU, 
DLEU, and free variable DFIX commands for C-C and C-N bond distances were 
applied. The reflection 0 0 1 was also omitted. 
;

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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_
_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 -0.28331(11) 0.71197(3) -0.02543(3) 0.04047(14) Uani 1 1 d . . . . .
Br2 Br 0.03756(12) 0.69158(4) 0.15419(3) 0.04394(15) Uani 1 1 d . . . . .
Br3 Br 0.54248(12) 0.21551(3) 0.44405(3) 0.04431(15) Uani 1 1 d . . . . .
Br4 Br 0.88595(11) 0.19968(3) 0.62334(3) 0.04198(14) Uani 1 1 d . . . . .
N1 N 0.5901(10) 0.4700(3) 0.2345(2) 0.0456(10) Uani 1 1 d . . . . .
C1 C 0.5738(11) 0.5481(4) 0.2961(3) 0.0411(11) Uani 1 1 d . . . . .
H1 H 0.470902 0.605336 0.286965 0.049 Uiso 1 1 calc R U . . .
C2 C 0.6982(10) 0.5505(3) 0.3726(2) 0.0348(10) Uani 1 1 d . . . . .
H2 H 0.676473 0.607351 0.414076 0.042 Uiso 1 1 calc R U . . .
C3 C 0.8550(10) 0.4681(3) 0.3874(2) 0.0301(9) Uani 1 1 d . . . . .
C4 C 0.8700(11) 0.3868(3) 0.3253(3) 0.0408(11) Uani 1 1 d . . . . .
H4 H 0.968481 0.328336 0.333117 0.049 Uiso 1 1 calc R U . . .
C5 C 0.7383(12) 0.3914(4) 0.2503(3) 0.0472(12) Uani 1 1 d . . . . .
H5 H 0.755218 0.335053 0.208044 0.057 Uiso 1 1 calc R U . . .
C6 C 1.0025(10) 0.4651(3) 0.4674(2) 0.0323(10) Uani 1 1 d . . . . .
H6 H 1.110608 0.4067 0.471493 0.039 Uiso 1 1 calc R U . . .
C7 C 0.1354(9) 0.4913(3) 0.0733(2) 0.0299(9) Uani 1 1 d . . . . .
H7 H 0.228161 0.485561 0.123142 0.036 Uiso 1 1 calc R U . . .
C8 C 0.0153(9) 0.5819(3) 0.0644(2) 0.0301(9) Uani 1 1 d . . . . .
C9 C -0.1190(9) 0.5895(3) -0.0098(2) 0.0285(9) Uani 1 1 d . . . . .
N2A N 0.8851(15) 0.0237(5) 0.2666(3) 0.0423(14) Uani 0.948(10) 1 d . U P A 1
C10A C 0.9915(19) 0.0985(5) 0.2344(4) 0.0452(16) Uani 0.948(10) 1 d . U P A 1
H10A H 1.134906 0.152428 0.266239 0.054 Uiso 0.948(10) 1 calc R U P A 1
C11A C 0.9073(17) 0.1034(5) 0.1569(4) 0.0397(15) Uani 0.948(10) 1 d . U P A 1
H11A H 0.9918 0.159321 0.137351 0.048 Uiso 0.948(10) 1 calc R U P A 1
C12A C 0.699(2) 0.0259(6) 0.1086(3) 0.0343(11) Uani 0.948(10) 1 d D U P A 1
C13A C 0.5841(15) -0.0542(5) 0.1416(4) 0.0374(15) Uani 0.948(10) 1 d . U P A 1
H13A H 0.439163 -0.108975 0.111388 0.045 Uiso 0.948(10) 1 calc R U P A 1
C14A C 0.6870(14) -0.0515(5) 0.2194(4) 0.0393(14) Uani 0.948(10) 1 d . U P A 1
H14A H 0.611436 -0.106879 0.24059 0.047 Uiso 0.948(10) 1 calc R U P A 1
C15A C 0.6061(11) 0.0316(4) 0.0253(3) 0.0339(14) Uani 0.948(10) 1 d D U P A 1
H15A H 0.711034 0.086419 0.007611 0.041 Uiso 0.948(10) 1 calc R U P A 1
N2B N 0.94(3) 0.030(10) 0.256(5) 0.038(5) Uani 0.052(10) 1 d G U P A 2
C10B C 0.97(3) 0.116(8) 0.224(6) 0.039(5) Uani 0.052(10) 1 d G U P A 2
H10B H 1.080336 0.178009 0.255019 0.046 Uiso 0.052(10) 1 calc R U P A 2
C11B C 0.84(4) 0.111(9) 0.147(7) 0.037(5) Uani 0.052(10) 1 d G U P A 2
H11B H 0.861928 0.169177 0.125621 0.044 Uiso 0.052(10) 1 calc R U P A 2
C12B C 0.68(3) 0.020(10) 0.102(5) 0.035(4) Uani 0.052(10) 1 d DG U P A 2
C13B C 0.65(3) -0.066(8) 0.134(7) 0.035(5) Uani 0.052(10) 1 d G U P A 2
H13B H 0.545242 -0.127696 0.103023 0.042 Uiso 0.052(10) 1 calc R U P A 2
C14B C 0.78(3) -0.061(8) 0.211(7) 0.037(5) Uani 0.052(10) 1 d G U P A 2
H14B H 0.763648 -0.118866 0.232421 0.045 Uiso 0.052(10) 1 calc R U P A 2
C15B C 0.50(2) -0.031(5) 0.024(4) 0.034(6) Uani 0.052(10) 1 d D U P A 2
H15B H 0.401297 -0.098395 0.01077 0.04 Uiso 0.052(10) 1 calc R U P A 2
C16 C 0.6459(9) -0.0074(3) 0.5725(2) 0.0285(9) Uani 1 1 d . . . . .
H16 H 0.745785 -0.012265 0.621947 0.034 Uiso 1 1 calc R U . . .
C17 C 0.6631(9) 0.0855(3) 0.5510(2) 0.0275(9) Uani 1 1 d . . . . .
C18 C 0.5164(9) 0.0922(3) 0.4779(2) 0.0276(9) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C9 1.891(4) . ?
Br2 C8 1.886(4) . ?
Br3 C18 1.880(4) . ?
Br4 C17 1.883(4) . ?
N1 C5 1.325(6) . ?
N1 C1 1.331(6) . ?
C1 C2 1.379(6) . ?
C1 H1 0.94 . ?
C2 C3 1.380(6) . ?
C2 H2 0.94 . ?
C3 C4 1.363(6) . ?
C3 C6 1.483(5) . ?
C4 C5 1.387(6) . ?
C4 H4 0.94 . ?
C5 H5 0.94 . ?
C6 C6 1.301(8) 2_766 ?
C6 H6 0.94 . ?
C7 C9 1.360(5) 2_565 ?
C7 C8 1.383(5) . ?
C7 H7 0.94 . ?
C8 C9 1.390(5) . ?
N2A C10A 1.312(7) . ?
N2A C14A 1.326(6) . ?
C10A C11A 1.381(6) . ?
C10A H10A 0.94 . ?
C11A C12A 1.372(6) . ?
C11A H11A 0.94 . ?
C12A C13A 1.390(6) . ?
C12A C15A 1.487(7) . ?
C13A C14A 1.377(6) . ?
C13A H13A 0.94 . ?
C14A H14A 0.94 . ?
C15A C15A 1.299(8) 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 1.368(5) 2_656 ?
C16 C17 1.383(5) . ?
C16 H16 0.94 . ?
C17 C18 1.387(5) . ?

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
_geom_angle_publ_flag
C5 N1 C1 115.8(4) . . ?
N1 C1 C2 124.1(4) . . ?
N1 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
C1 C2 C3 119.0(4) . . ?
C1 C2 H2 120.5 . . ?
C3 C2 H2 120.5 . . ?
C4 C3 C2 117.6(4) . . ?
C4 C3 C6 119.7(4) . . ?
C2 C3 C6 122.7(4) . . ?
C3 C4 C5 119.3(4) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
N1 C5 C4 124.1(4) . . ?
N1 C5 H5 117.9 . . ?
C4 C5 H5 117.9 . . ?
C6 C6 C3 126.7(5) 2_766 . ?
C6 C6 H6 116.7 2_766 . ?
C3 C6 H6 116.7 . . ?
C9 C7 C8 119.8(4) 2_565 . ?
C9 C7 H7 120.1 2_565 . ?
C8 C7 H7 120.1 . . ?
C7 C8 C9 119.4(4) . . ?
C7 C8 Br2 118.5(3) . . ?
C9 C8 Br2 122.1(3) . . ?
C7 C9 C8 120.8(4) 2_565 . ?
C7 C9 Br1 118.1(3) 2_565 . ?
C8 C9 Br1 121.1(3) . . ?
C10A N2A C14A 115.9(4) . . ?
N2A C10A C11A 124.5(5) . . ?
N2A C10A H10A 117.8 . . ?
C11A C10A H10A 117.8 . . ?
C12A C11A C10A 119.4(5) . . ?
C12A C11A H11A 120.3 . . ?
C10A C11A H11A 120.3 . . ?
C11A C12A C13A 117.1(4) . . ?
C11A C12A C15A 119.4(6) . . ?
C13A C12A C15A 123.5(6) . . ?
C14A C13A C12A 118.5(4) . . ?
C14A C13A H13A 120.7 . . ?
C12A C13A H13A 120.7 . . ?
N2A C14A C13A 124.6(5) . . ?
N2A C14A H14A 117.7 . . ?
C13A C14A H14A 117.7 . . ?
C15A C15A C12A 126.4(7) 2_655 . ?
C15A C15A H15A 116.8 2_655 . ?
C12A C15A H15A 116.8 . . ?
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 95(8) . . ?
C11B C12B C15B 145(8) . . ?
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 111(8) 2_655 . ?
C15B C15B H15B 124.7 2_655 . ?
C12B C15B H15B 124.7 . . ?
C18 C16 C17 120.1(4) 2_656 . ?
C18 C16 H16 120 2_656 . ?
C17 C16 H16 120 . . ?
C16 C17 C18 119.8(3) . . ?
C16 C17 Br4 118.1(3) . . ?
C18 C17 Br4 122.1(3) . . ?
C16 C18 C17 120.1(4) 2_656 . ?
C16 C18 Br3 118.1(3) 2_656 . ?
C17 C18 Br3 121.7(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 2.4 3.318(5) 166.1 .
C16 H16 N2A 0.94 2.4 3.321(6) 167.2 2_756
C16 H16 N2B 0.94 2.45 3.39(8) 174.2 2_756

_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_TBrB_BPE_190K
_database_code_depnum_ccdc_archive 'CCDC 1889839'
loop_
_audit_author_name
_audit_author_address
'Daniel Unruh'
;Texas Tech University
United States of America
;
_audit_update_record             
;
2019-01-09 deposited with the CCDC.	2019-02-21 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT250_TBrB_BPE_190K       
;
PROBLEM: Large U3/U1 Ratio for Average U(i,j) Tensor ....        2.2 Note  
RESPONSE: The 1,2-bis(4-pyridyl)ethylene molecule rotates very slightly about 
          C3 atom site.  Attempts to model split positions similar to the 
          structure at higher temperatures did not improve the model.
;
_vrf_PLAT911_TBrB_BPE_190K       
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600         46 Report
RESPONSE: These reflections were not collected.
;
_vrf_PLAT971_TBrB_BPE_190K       
;
PROBLEM: Check Calcd Resid. Dens.  0.97A   From Br2             2.06 eA-3  
RESPONSE: There were some issues with the absorption correction.
;
# end Validation Reply Form

_audit_creation_date             2018-10-31T15:21:35-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C18 H12 Br4 N2'
_chemical_formula_weight         575.94

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   3.9240(8)
_cell_length_b                   9.667(2)
_cell_length_c                   12.375(3)
_cell_angle_alpha                75.801(10)
_cell_angle_beta                 84.980(11)
_cell_angle_gamma                78.541(11)
_cell_volume                     445.65(17)
_cell_formula_units_Z            1
_cell_measurement_temperature    189(2)
_cell_measurement_reflns_used    3186
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      27.45

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.468
_exptl_crystal_size_mid          0.202
_exptl_crystal_size_min          0.177
_exptl_crystal_density_diffrn    2.146
_exptl_crystal_F_000             274

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    9.033
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_correction_T_max  0.8621
_exptl_absorpt_correction_T_min  0.5748
_shelx_estimated_absorpt_T_min   0.101
_shelx_estimated_absorpt_T_max   0.298

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      189(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_av_R_equivalents  0.0879
_diffrn_reflns_av_unetI/netI     0.0585
_diffrn_reflns_number            6392
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.699
_diffrn_reflns_theta_max         27.552
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.99
_diffrn_measured_fraction_theta_max 0.96
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.96
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.96
_reflns_Friedel_coverage         0
_reflns_number_total             1972
_reflns_number_gt                1587
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0728P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1972
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0535
_refine_ls_R_factor_gt           0.0451
_refine_ls_wR_factor_ref         0.1181
_refine_ls_wR_factor_gt          0.1148
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         2.024
_refine_diff_density_min         -1.164
_refine_diff_density_rms         0.191

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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_
_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 0.57426(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 . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
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_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
_geom_angle_publ_flag
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_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


# END of CIF



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
