# Supplementary Information (SI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2371849'
loop_
_audit_author_name
_audit_author_address
'Daniel Fortin'
;Universite de Sherbrooke
Canada
;
_audit_update_record             
;
2024-07-18 deposited with the CCDC.	2024-09-16 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_STRVA01_shelx               
;
PROBLEM: Flack test results are meaningless.
RESPONSE: No omission or oversight. The space group is non-centrosymmetric and with the Mo source the Flack test is meaningless. The missing reflections are near beam stop or really bad, or geometrically not observed.
;
_vrf_PLAT340_shelx               
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00433 Ang.
RESPONSE: No omission or oversight
;
# Added during the CSD deposition process: Thursday 18 July 2024 02:19 PM
# end Validation Reply Form


_audit_creation_date             2024-01-18T08:58:24-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_formula_moiety         'C16 H8 N2'
_chemical_formula_sum            'C16 H8 N2'
_chemical_formula_weight         228.24
_chemical_absolute_configuration unk

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   3.8662(5)
_cell_length_b                   9.2585(12)
_cell_length_c                   30.669(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1097.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5634
_cell_measurement_theta_min      2.3
_cell_measurement_theta_max      25.88
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       Needle
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.21
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472

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

_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
        SADABS-2016/2 - Bruker AXS area detector scaling and absorption correcti
;
_exptl_absorpt_correction_T_min  0.6
_exptl_absorpt_correction_T_max  0.745
_shelx_estimated_absorpt_T_min   0.944
_shelx_estimated_absorpt_T_max   0.983

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

_diffrn_source                   'sealed x-ray tube'
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector                 'APEX-II CCD'
_diffrn_orient_matrix_type       'x-axis to radiation source'
_diffrn_orient_matrix_ub_11      0.008946
_diffrn_orient_matrix_ub_12      0.10184
_diffrn_orient_matrix_ub_13      -0.010803
_diffrn_orient_matrix_ub_21      0.032624
_diffrn_orient_matrix_ub_22      -0.035965
_diffrn_orient_matrix_ub_23      -0.030469
_diffrn_orient_matrix_ub_31      -0.25643
_diffrn_orient_matrix_ub_32      -0.001023
_diffrn_orient_matrix_ub_33      -0.004253
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_number            5706
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.298
_diffrn_reflns_theta_max         25.88
_diffrn_reflns_theta_full        25
_diffrn_measured_fraction_theta_full 0.98
_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.98
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.951
_diffrn_reflns_point_group_measured_fraction_max 0.93
_reflns_Friedel_fraction_full    0.904
_reflns_Friedel_fraction_max     0.863
_reflns_Friedel_coverage         0.556
_reflns_number_total             1993
_reflns_number_gt                1816
_reflns_threshold_expression     'I > 2σ(I)'

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

_computing_data_collection       'Bruker APEX2 software'
_computing_cell_refinement       'SAINT V8.38A integration software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

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

_atom_sites_solution_hydrogens   geom

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

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0339P)²+0.6465P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1993
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1141
_refine_ls_wR_factor_gt          0.1122
_refine_ls_goodness_of_fit_ref   1.129
_refine_ls_restrained_S_all      1.129
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 590 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(10)
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.056

#----------------------------------------------------------------------------#
#                   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'

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
C1 C 0.5449(8) 0.6260(3) 0.62174(9) 0.0209(7) Uani 1 1 d . . . . .
C2 C 0.4302(8) 0.5573(3) 0.66291(9) 0.0208(7) Uani 1 1 d . . . . .
C3 C 0.2723(8) 0.6151(4) 0.69970(9) 0.0250(7) Uani 1 1 d . . . . .
H3 H 0.21548 0.714849 0.701111 0.03 Uiso 1 1 calc R U . . .
C4 C 0.1997(9) 0.5231(4) 0.73447(10) 0.0296(8) Uani 1 1 d . . . . .
H4 H 0.091484 0.560577 0.759873 0.036 Uiso 1 1 calc R U . . .
C5 C 0.2821(9) 0.3792(4) 0.73251(10) 0.0306(8) Uani 1 1 d . . . . .
H5 H 0.232379 0.318922 0.756773 0.037 Uiso 1 1 calc R U . . .
C6 C 0.4372(8) 0.3197(4) 0.69570(9) 0.0253(7) Uani 1 1 d . . . . .
H6 H 0.489795 0.21957 0.694313 0.03 Uiso 1 1 calc R U . . .
C7 C 0.5124(8) 0.4107(3) 0.66121(9) 0.0206(7) Uani 1 1 d . . . . .
C8 C 0.6797(8) 0.3803(3) 0.61913(9) 0.0207(6) Uani 1 1 d . . . . .
C9 C 0.8068(9) 0.2533(4) 0.60257(10) 0.0273(7) Uani 1 1 d . . . . .
H9 H 0.79487 0.166437 0.618999 0.033 Uiso 1 1 calc R U . . .
C10 C 0.9540(9) 0.2546(4) 0.56106(10) 0.0298(8) Uani 1 1 d . . . . .
H10 H 1.043753 0.167786 0.549028 0.036 Uiso 1 1 calc R U . . .
C11 C 0.9702(9) 0.3813(4) 0.53727(9) 0.0297(8) Uani 1 1 d . . . . .
H11 H 1.070923 0.380024 0.509014 0.036 Uiso 1 1 calc R U . . .
C12 C 0.8430(9) 0.5096(4) 0.55375(9) 0.0263(8) Uani 1 1 d . . . . .
H12 H 0.853856 0.596059 0.537105 0.032 Uiso 1 1 calc R U . . .
C13 C 0.6986(8) 0.5092(3) 0.59532(9) 0.0199(7) Uani 1 1 d . . . . .
C14 C 0.5191(9) 0.7674(3) 0.61103(9) 0.0241(7) Uani 1 1 d . . . . .
C15 C 0.6570(10) 0.8270(4) 0.57133(10) 0.0305(8) Uani 1 1 d . . . . .
C16 C 0.3579(9) 0.8728(4) 0.63857(10) 0.0292(8) Uani 1 1 d . . . . .
N1 N 0.7715(10) 0.8797(4) 0.54100(10) 0.0477(9) Uani 1 1 d . . . . .
N2 N 0.2252(9) 0.9585(3) 0.65953(10) 0.0420(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
C1 C14 1.353(4) . ?
C1 C13 1.476(4) . ?
C1 C2 1.482(4) . ?
C2 C3 1.390(4) . ?
C2 C7 1.395(4) . ?
C3 C4 1.393(4) . ?
C4 C5 1.371(5) . ?
C5 C6 1.392(5) . ?
C6 C7 1.383(4) . ?
C7 C8 1.471(4) . ?
C8 C9 1.372(4) . ?
C8 C13 1.401(4) . ?
C9 C10 1.395(4) . ?
C10 C11 1.383(5) . ?
C11 C12 1.382(5) . ?
C12 C13 1.392(4) . ?
C14 C16 1.433(4) . ?
C14 C15 1.439(4) . ?
C15 N1 1.140(4) . ?
C16 N2 1.143(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
C14 C1 C13 127.2(3) . . ?
C14 C1 C2 126.9(3) . . ?
C13 C1 C2 105.9(2) . . ?
C3 C2 C7 120.3(3) . . ?
C3 C2 C1 131.1(3) . . ?
C7 C2 C1 108.5(2) . . ?
C2 C3 C4 118.3(3) . . ?
C5 C4 C3 120.9(3) . . ?
C4 C5 C6 121.4(3) . . ?
C7 C6 C5 118.0(3) . . ?
C6 C7 C2 121.1(3) . . ?
C6 C7 C8 130.3(3) . . ?
C2 C7 C8 108.6(2) . . ?
C9 C8 C13 121.2(3) . . ?
C9 C8 C7 130.3(3) . . ?
C13 C8 C7 108.5(3) . . ?
C8 C9 C10 118.5(3) . . ?
C11 C10 C9 120.5(3) . . ?
C12 C11 C10 121.4(3) . . ?
C11 C12 C13 118.4(3) . . ?
C12 C13 C8 120.0(3) . . ?
C12 C13 C1 131.5(3) . . ?
C8 C13 C1 108.5(2) . . ?
C1 C14 C16 123.2(3) . . ?
C1 C14 C15 123.3(3) . . ?
C16 C14 C15 113.5(3) . . ?
N1 C15 C14 176.8(4) . . ?
N2 C16 C14 178.1(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 C1 C2 C3 0.3(6) . . . . ?
C13 C1 C2 C3 179.2(3) . . . . ?
C14 C1 C2 C7 -178.5(3) . . . . ?
C13 C1 C2 C7 0.5(3) . . . . ?
C7 C2 C3 C4 0.0(4) . . . . ?
C1 C2 C3 C4 -178.6(3) . . . . ?
C2 C3 C4 C5 0.1(5) . . . . ?
C3 C4 C5 C6 -0.7(5) . . . . ?
C4 C5 C6 C7 1.2(5) . . . . ?
C5 C6 C7 C2 -1.1(5) . . . . ?
C5 C6 C7 C8 178.6(3) . . . . ?
C3 C2 C7 C6 0.5(4) . . . . ?
C1 C2 C7 C6 179.4(3) . . . . ?
C3 C2 C7 C8 -179.2(3) . . . . ?
C1 C2 C7 C8 -0.3(3) . . . . ?
C6 C7 C8 C9 0.0(6) . . . . ?
C2 C7 C8 C9 179.7(3) . . . . ?
C6 C7 C8 C13 -179.7(3) . . . . ?
C2 C7 C8 C13 0.0(3) . . . . ?
C13 C8 C9 C10 -0.5(5) . . . . ?
C7 C8 C9 C10 179.8(3) . . . . ?
C8 C9 C10 C11 -0.1(5) . . . . ?
C9 C10 C11 C12 0.1(6) . . . . ?
C10 C11 C12 C13 0.4(5) . . . . ?
C11 C12 C13 C8 -1.0(5) . . . . ?
C11 C12 C13 C1 179.7(3) . . . . ?
C9 C8 C13 C12 1.1(5) . . . . ?
C7 C8 C13 C12 -179.2(3) . . . . ?
C9 C8 C13 C1 -179.4(3) . . . . ?
C7 C8 C13 C1 0.3(3) . . . . ?
C14 C1 C13 C12 -2.2(6) . . . . ?
C2 C1 C13 C12 178.9(3) . . . . ?
C14 C1 C13 C8 178.5(3) . . . . ?
C2 C1 C13 C8 -0.5(3) . . . . ?
C13 C1 C14 C16 178.6(3) . . . . ?
C2 C1 C14 C16 -2.7(5) . . . . ?
C13 C1 C14 C15 -2.7(5) . . . . ?
C2 C1 C14 C15 176.0(3) . . . . ?



# END of CIF
_chemical_name_systematic        '9-fluorenylidene malononitrile'
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_Harvey_LB3_115_c_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2371850'
loop_
_audit_author_name
_audit_author_address
'Daniel Fortin'
;Universite de Sherbrooke
Canada
;
_audit_update_record             
;
2024-07-18 deposited with the CCDC.	2024-09-16 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT341_Harvey_LB3_115_c_0m_a 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01094 Ang.
RESPONSE: No omission or oversight
;
_vrf_PLAT906_Harvey_LB3_115_c_0m_a 
;
PROBLEM: Large K Value in the Analysis of Variance ......      2.488 Check
RESPONSE: No omission or oversight
;
_vrf_PLAT911_Harvey_LB3_115_c_0m_a 
;
PROBLEM: Missing FCF Refl Between Thmin & STh/L=    0.600          6 Report
RESPONSE: No omission or oversight
;
_vrf_PLAT924_Harvey_LB3_115_c_0m_a 
;
PROBLEM: The Reported and Calculated Rho(min) Differ by .       1.05 eA-3
RESPONSE: No omission or oversight
;
_vrf_PLAT925_Harvey_LB3_115_c_0m_a 
;
PROBLEM: The Reported and Calculated Rho(max) Differ by .       1.20 eA-3
RESPONSE: No omission or oversight
;
# Added during the CSD deposition process: Thursday 18 July 2024 02:19 PM
# end Validation Reply Form

_audit_creation_date             2024-03-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         'C32 H16 Br2 Cu2 N4'
_chemical_formula_sum            'C32 H16 Br2 Cu2 N4'
_chemical_formula_weight         743.41
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Br -0.28346 2.55990 17.17890 5.23580 5.63770 3.98510 2.17230 16.57960 0.26090
41.43280 2.95569992065
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cu 0.34125 1.28947 13.33800 7.16760 5.61580 1.67350 3.58280 0.24700 11.39660
64.81260 1.19099998474
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   13.4481(17)
_cell_length_b                   14.4239(18)
_cell_length_c                   14.2542(18)
_cell_angle_alpha                90
_cell_angle_beta                 113.978(2)
_cell_angle_gamma                90
_cell_volume                     2526.3(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9843
_cell_measurement_temperature    173.21
_cell_measurement_theta_max      26.370
_cell_measurement_theta_min      2.178
_exptl_absorpt_coefficient_mu    4.879
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4659
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0985 before and 0.0628 after correction.
The Ratio of minimum to maximum transmission is 0.6250.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            'metallic black'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.9544
_exptl_crystal_description       needle
_exptl_crystal_F_000             1456.9826
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.085
_exptl_crystal_size_min          0.075
_diffrn_reflns_av_R_equivalents  0.0984
_diffrn_reflns_av_unetI/netI     0.0845
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            33196
_diffrn_reflns_theta_full        25.0000
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         1.76
_diffrn_ambient_temperature      173.21
_diffrn_measured_fraction_theta_full 0.9986
_diffrn_measured_fraction_theta_max 0.9965
_diffrn_measurement_device_type  'Bruker APEX-DUO'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              9
_reflns_limit_h_min              -16
_reflns_limit_k_max              18
_reflns_limit_k_min              0
_reflns_limit_l_max              17
_reflns_limit_l_min              -8
_reflns_number_gt                3132
_reflns_number_total             5155
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         1.8386
_refine_diff_density_min         -1.6859
_refine_diff_density_rms         0.3710
_refine_ls_d_res_high            0.7996
_refine_ls_d_res_low             11.5936
_refine_ls_goodness_of_fit_ref   1.0878
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    32
_refine_ls_number_parameters     361
_refine_ls_number_reflns         5155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1118
_refine_ls_R_factor_gt           0.0530
_refine_ls_restrained_S_all      1.0878
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0272P)²+17.4504P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1001
_refine_ls_wR_factor_ref         0.1219
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 c9(H9), c8(H8), c7(H7), c6(H6), c15(H15), c14(H14), c13(H13), c12(H12),
 c25(H25), c24(H24), c23(H23), c22(H22), c31(H31), c30(H30), c29(H29), c28(H28)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
Br1 Br -0.04942(6) 0.03758(5) 0.62316(6) 0.01854(19) Uani 1.000000 .
Br2 Br 0.44717(6) 0.64967(5) 0.60947(5) 0.01842(19) Uani 1.000000 .
Cu1 Cu -0.03980(7) 0.18999(6) 0.70260(7) 0.0203(2) Uani 1.000000 .
Cu2 Cu 0.45485(7) 0.49682(6) 0.69212(7) 0.0199(2) Uani 1.000000 .
n1 N 0.0349(5) 0.2938(4) 0.6696(5) 0.0178(14) Uani 1.000000 .
N2 N 0.3021(5) 0.4588(4) 0.6663(4) 0.0171(13) Uani 1.000000 .
n3 N 0.5313(5) 0.3932(4) 0.6608(5) 0.0181(14) Uani 1.000000 .
n4 N 0.8062(5) 0.2277(4) 0.6685(5) 0.0246(15) Uani 1.000000 .
c1 C 0.0644(5) 0.3644(5) 0.6565(5) 0.0122(15) Uani 1.000000 .
c2 C 0.1020(6) 0.4544(5) 0.6407(5) 0.0140(15) Uani 1.000000 .
c3 C 0.2146(6) 0.4559(5) 0.6554(5) 0.0156(16) Uani 1.000000 .
c4 C 0.0387(6) 0.5324(5) 0.6208(5) 0.0127(15) Uani 1.000000 .
c5 C 0.0729(6) 0.6280(5) 0.6118(5) 0.0134(15) Uani 1.000000 .
c6 C 0.1695(6) 0.6631(5) 0.6129(5) 0.0168(16) Uani 1.000000 .
c7 C 0.1800(6) 0.7598(5) 0.6072(6) 0.0196(17) Uani 1.000000 .
c8 C 0.0954(6) 0.8184(5) 0.5999(5) 0.0205(17) Uani 1.000000 .
c9 C -0.0019(6) 0.7833(5) 0.5992(5) 0.0182(16) Uani 1.000000 .
c10 C -0.0126(6) 0.6888(5) 0.6032(5) 0.0154(16) Uani 1.000000 .
c11 C -0.1054(6) 0.6319(5) 0.6006(5) 0.0129(15) Uani 1.000000 .
c12 C -0.2083(6) 0.6582(6) 0.5915(5) 0.0225(18) Uani 1.000000 .
c13 C -0.2825(6) 0.5911(5) 0.5884(5) 0.0209(17) Uani 1.000000 .
c14 C -0.2529(6) 0.4977(6) 0.5959(6) 0.0238(18) Uani 1.000000 .
c15 C -0.1506(6) 0.4692(5) 0.6065(5) 0.0172(16) Uani 1.000000 .
c16 C -0.0759(5) 0.5379(5) 0.6094(5) 0.0128(15) Uani 1.000000 .
c17 C 0.5649(6) 0.3224(5) 0.6550(5) 0.0143(15) Uani 1.000000 .
c18 C 0.6067(5) 0.2316(5) 0.6495(5) 0.0135(15) Uani 1.000000 .
c19 C 0.7162(6) 0.2301(5) 0.6582(5) 0.0131(15) Uani 1.000000 .
c20 C 0.5483(5) 0.1515(5) 0.6423(5) 0.0112(14) Uani 1.000000 .
c21 C 0.4348(5) 0.1464(5) 0.6337(5) 0.0123(15) Uani 1.000000 .
c22 C 0.3613(6) 0.2131(5) 0.6346(5) 0.0168(16) Uani 1.000000 .
c23 C 0.2576(6) 0.1837(5) 0.6226(5) 0.0185(16) Uani 1.000000 .
c24 C 0.2279(6) 0.0924(6) 0.6103(6) 0.0239(18) Uani 1.000000 .
c25 C 0.3012(6) 0.0251(5) 0.6102(5) 0.0167(16) Uani 1.000000 .
c26 C 0.4048(5) 0.0509(5) 0.6233(5) 0.0122(15) Uani 1.000000 .
c27 C 0.4969(6) -0.0047(5) 0.6257(5) 0.0119(15) Uani 1.000000 .
c28 C 0.5082(6) -0.0996(5) 0.6193(5) 0.0188(17) Uani 1.000000 .
c29 C 0.6068(6) -0.1344(5) 0.6242(5) 0.0182(17) Uani 1.000000 .
c30 C 0.6914(6) -0.0749(5) 0.6344(5) 0.0176(16) Uani 1.000000 .
c31 C 0.6828(5) 0.0199(5) 0.6430(5) 0.0136(15) Uani 1.000000 .
c32 C 0.5845(5) 0.0558(5) 0.6378(5) 0.0129(15) Uani 1.000000 .
H9 H -0.0590(6) 0.8237(5) 0.5962(5) 0.022(2) Uiso 1.000000 R
H8 H 0.1036(6) 0.8834(5) 0.5951(5) 0.025(2) Uiso 1.000000 R
H7 H 0.2457(6) 0.7852(5) 0.6084(6) 0.024(2) Uiso 1.000000 R
H6 H 0.2271(6) 0.6228(5) 0.6175(5) 0.0202(19) Uiso 1.000000 R
H15 H -0.1318(6) 0.4054(5) 0.6116(5) 0.0206(19) Uiso 1.000000 R
H14 H -0.3048(6) 0.4521(6) 0.5936(6) 0.029(2) Uiso 1.000000 R
H13 H -0.3534(6) 0.6083(5) 0.5812(5) 0.025(2) Uiso 1.000000 R
H12 H -0.2274(6) 0.7219(6) 0.5875(5) 0.027(2) Uiso 1.000000 R
H25 H 0.2803(6) -0.0383(5) 0.6013(5) 0.0201(19) Uiso 1.000000 R
H24 H 0.1566(6) 0.0751(6) 0.6018(6) 0.029(2) Uiso 1.000000 R
H23 H 0.2062(6) 0.2287(5) 0.6229(5) 0.022(2) Uiso 1.000000 R
H22 H 0.3807(6) 0.2768(5) 0.6432(5) 0.0202(19) Uiso 1.000000 R
H31 H 0.7424(5) 0.0596(5) 0.6523(5) 0.0164(18) Uiso 1.000000 R
H30 H 0.7572(6) -0.0999(5) 0.6355(5) 0.021(2) Uiso 1.000000 R
H29 H 0.6161(6) -0.1994(5) 0.6204(5) 0.022(2) Uiso 1.000000 R
H28 H 0.4498(6) -0.1402(5) 0.6118(5) 0.023(2) Uiso 1.000000 R


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 Cu1 2.4520(12) . ?
Br1 Cu2 2.4848(12) 2_546 ?
Br2 Cu1 2.5206(12) 2_556 ?
Br2 Cu2 2.4819(12) . ?
Cu1 n1 1.964(6) . ?
Cu1 n4 2.002(6) 1_455 ?
Cu2 N2 2.010(6) . ?
Cu2 n3 1.965(6) . ?
n1 c1 1.135(8) . ?
N2 c3 1.123(9) . ?
n3 c17 1.134(9) . ?
n4 c19 1.158(8) . ?
c1 c2 1.444(9) . ?
c2 c3 1.443(10) . ?
c2 c4 1.369(10) . ?
c4 c5 1.475(9) . ?
c4 c16 1.485(9) . ?
c5 c6 1.388(9) . ?
c5 c10 1.412(9) . ?
c6 c7 1.408(9) . ?
c7 c8 1.387(10) . ?
c8 c9 1.399(10) . ?
c9 c10 1.374(10) . ?
c10 c11 1.482(10) . ?
c11 c12 1.389(10) . ?
c11 c16 1.405(9) . ?
c12 c13 1.378(10) . ?
c13 c14 1.397(11) . ?
c14 c15 1.384(10) . ?
c15 c16 1.399(9) . ?
c17 c18 1.439(10) . ?
c18 c19 1.427(9) . ?
c18 c20 1.378(9) . ?
c20 c21 1.483(9) . ?
c20 c32 1.474(9) . ?
c21 c22 1.382(9) . ?
c21 c26 1.425(9) . ?
c22 c23 1.400(9) . ?
c23 c24 1.366(10) . ?
c24 c25 1.384(10) . ?
c25 c26 1.380(9) . ?
c26 c27 1.464(9) . ?
c27 c28 1.384(10) . ?
c27 c32 1.419(9) . ?
c28 c29 1.393(10) . ?
c29 c30 1.384(10) . ?
c30 c31 1.382(10) . ?
c31 c32 1.392(9) . ?

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
Cu2 Br1 Cu1 79.31(4) 2_546 . ?
Cu2 Br2 Cu1 78.07(4) . 2_556 ?
Br2 Cu1 Br1 101.21(4) 2_546 . ?
n1 Cu1 Br1 120.60(17) . . ?
n1 Cu1 Br2 110.53(18) . 2_546 ?
n4 Cu1 Br1 106.06(19) 1_455 . ?
n4 Cu1 Br2 109.67(19) 1_455 2_546 ?
n4 Cu1 n1 108.3(2) 1_455 . ?
Br2 Cu2 Br1 101.39(4) . 2_556 ?
N2 Cu2 Br1 107.64(17) . 2_556 ?
N2 Cu2 Br2 108.24(17) . . ?
n3 Cu2 Br1 109.31(18) . 2_556 ?
n3 Cu2 Br2 119.51(17) . . ?
n3 Cu2 N2 109.9(2) . . ?
c1 n1 Cu1 165.9(6) . . ?
c3 N2 Cu2 166.1(6) . . ?
c17 n3 Cu2 164.4(6) . . ?
c19 n4 Cu1 164.4(6) . 1_655 ?
c2 c1 n1 179.5(7) . . ?
c3 c2 c1 113.9(6) . . ?
c4 c2 c1 123.0(6) . . ?
c4 c2 c3 123.0(6) . . ?
c2 c3 N2 178.7(8) . . ?
c5 c4 c2 126.6(6) . . ?
c16 c4 c2 126.6(6) . . ?
c16 c4 c5 106.7(6) . . ?
c6 c5 c4 131.6(6) . . ?
c10 c5 c4 108.5(6) . . ?
c10 c5 c6 119.9(6) . . ?
c7 c6 c5 118.5(7) . . ?
c8 c7 c6 120.6(7) . . ?
c9 c8 c7 121.1(7) . . ?
c10 c9 c8 118.1(7) . . ?
c9 c10 c5 121.7(7) . . ?
c11 c10 c5 107.8(6) . . ?
c11 c10 c9 130.5(6) . . ?
c12 c11 c10 130.4(7) . . ?
c16 c11 c10 109.2(6) . . ?
c16 c11 c12 120.4(7) . . ?
c13 c12 c11 119.5(7) . . ?
c14 c13 c12 119.7(7) . . ?
c15 c14 c13 122.3(7) . . ?
c16 c15 c14 117.6(7) . . ?
c11 c16 c4 107.7(6) . . ?
c15 c16 c4 131.8(6) . . ?
c15 c16 c11 120.5(6) . . ?
c18 c17 n3 178.5(7) . . ?
c19 c18 c17 114.9(6) . . ?
c20 c18 c17 123.0(6) . . ?
c20 c18 c19 122.0(6) . . ?
c18 c19 n4 177.7(7) . . ?
c21 c20 c18 125.8(6) . . ?
c32 c20 c18 126.9(6) . . ?
c32 c20 c21 107.3(6) . . ?
c22 c21 c20 132.8(6) . . ?
c26 c21 c20 107.1(6) . . ?
c26 c21 c22 120.0(6) . . ?
c23 c22 c21 117.9(7) . . ?
c24 c23 c22 122.1(7) . . ?
c25 c24 c23 120.4(7) . . ?
c26 c25 c24 119.4(7) . . ?
c25 c26 c21 120.1(6) . . ?
c27 c26 c21 109.1(6) . . ?
c27 c26 c25 130.8(7) . . ?
c28 c27 c26 130.9(6) . . ?
c32 c27 c26 108.6(6) . . ?
c32 c27 c28 120.5(6) . . ?
c29 c28 c27 118.8(7) . . ?
c30 c29 c28 120.4(7) . . ?
c31 c30 c29 121.8(7) . . ?
c32 c31 c30 118.4(6) . . ?
c27 c32 c20 107.9(6) . . ?
c31 c32 c20 132.0(6) . . ?
c31 c32 c27 120.1(6) . . ?


_olex2_submission_original_sample_id Harvey_LB3_115_c_0m_a
_olex2_submission_special_instructions 'No special instructions were received'
_chemical_name_systematic        UDS-6
_exptl_crystal_recrystallization_method 
'Reaction in a room temperature unstirred solution of ligand and CuBr in acetonitrile'
