# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_bhy-170_auto
_database_code_depnum_ccdc_archive 'CCDC 2217909'
loop_
_audit_author_name
_audit_author_address
'hongyi Bian'
;fjirsm
China
;
_audit_update_record             
;
2022-11-12 deposited with the CCDC.	2023-08-06 downloaded from the CCDC.
;
_audit_creation_date             2022-10-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            '[Cu(VIM)2(DCA)2]n'
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H12 Cu N10'
_chemical_formula_sum            'C14 H12 Cu N10'
_chemical_formula_weight         383.88
_chemical_melting_point          ?
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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.5089(3)
_cell_length_b                   7.4005(4)
_cell_length_c                   8.7801(4)
_cell_angle_alpha                105.113(4)
_cell_angle_beta                 96.853(4)
_cell_angle_gamma                95.783(4)
_cell_volume                     401.53(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2619
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      28.9730
_cell_measurement_theta_min      2.4250
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.381
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.588
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             195
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.816
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            3858
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.816
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.019
_diffrn_reflns_theta_min         2.431
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.816
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1570
_reflns_number_total             1736
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.596
_refine_diff_density_rms         0.081
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     123
_refine_ls_number_reflns         1736
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0356
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0447P)²+0.1087P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0842
_refine_ls_wR_factor_ref         0.0868
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C3(H3), C5(H5), C6(H6)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
Cu1 Cu 1.000000 0.000000 0.500000 0.01484(15) Uani 1 2 d S . P . .
N4 N 0.8012(3) -0.1197(3) 0.2980(2) 0.0144(4) Uani 1 1 d . . . . .
N1 N 0.8305(3) 0.2135(3) 0.5508(2) 0.0174(4) Uani 1 1 d . . . . .
N2 N 0.6696(3) 0.4959(3) 0.6593(2) 0.0194(4) Uani 1 1 d . . . . .
N5 N 0.5207(3) -0.1833(3) 0.1164(2) 0.0146(4) Uani 1 1 d . . . . .
N3 N 0.7710(3) 0.8158(3) 0.6347(2) 0.0184(4) Uani 1 1 d . . . . .
C2 C 0.7299(3) 0.6629(3) 0.6403(2) 0.0140(5) Uani 1 1 d . . . . .
C4 C 0.8369(4) -0.2508(3) 0.1626(3) 0.0163(5) Uani 1 1 d . . . . .
H4 H 0.962333 -0.304967 0.150800 0.020 Uiso 1 1 calc R U . . .
C3 C 0.6097(4) -0.0819(3) 0.2659(2) 0.0154(5) Uani 1 1 d . . . . .
H3 H 0.543312 0.004410 0.337648 0.018 Uiso 1 1 calc R U . . .
C5 C 0.6660(4) -0.2896(3) 0.0501(3) 0.0165(5) Uani 1 1 d . . . . .
H5 H 0.649258 -0.373647 -0.054227 0.020 Uiso 1 1 calc R U . . .
C1 C 0.7609(4) 0.3511(3) 0.5977(2) 0.0144(5) Uani 1 1 d . . . . .
C6 C 0.3214(4) -0.1641(3) 0.0427(3) 0.0175(5) Uani 1 1 d . . . . .
H6 H 0.240280 -0.082440 0.104723 0.021 Uiso 1 1 calc R U . . .
C7 C 0.2413(4) -0.2525(4) -0.1065(3) 0.0227(5) Uani 1 1 d . . . . .
H7A H 0.097(5) -0.230(4) -0.149(3) 0.037(8) Uiso 1 1 d . . . . .
H7B H 0.316(5) -0.340(5) -0.181(3) 0.037(8) Uiso 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0154(2) 0.0116(2) 0.0142(2) -0.00099(15) -0.00142(15) 0.00307(15)
N4 0.0147(10) 0.0133(10) 0.0138(9) 0.0021(7) 0.0011(7) 0.0016(8)
N1 0.0180(11) 0.0137(10) 0.0178(10) 0.0013(8) -0.0018(8) 0.0029(8)
N2 0.0238(12) 0.0133(10) 0.0225(11) 0.0032(8) 0.0098(8) 0.0064(8)
N5 0.0136(10) 0.0147(10) 0.0133(9) 0.0023(7) -0.0006(7) -0.0005(8)
N3 0.0189(11) 0.0161(11) 0.0184(10) 0.0023(8) 0.0015(8) 0.0025(8)
C2 0.0126(12) 0.0178(12) 0.0096(10) -0.0004(8) 0.0006(8) 0.0054(9)
C4 0.0158(12) 0.0152(12) 0.0157(11) 0.0005(9) 0.0032(9) 0.0010(9)
C3 0.0171(12) 0.0139(11) 0.0128(11) 0.0008(9) 0.0016(9) -0.0005(9)
C5 0.0175(12) 0.0153(11) 0.0138(11) -0.0007(8) 0.0030(9) 0.0010(9)
C1 0.0150(12) 0.0159(12) 0.0101(10) 0.0034(8) -0.0028(8) -0.0017(9)
C6 0.0132(12) 0.0169(12) 0.0212(12) 0.0048(9) -0.0005(9) 0.0009(9)
C7 0.0211(14) 0.0214(13) 0.0229(13) 0.0065(10) -0.0044(10) -0.0022(11)

_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
Cu1 N4 2.0022(17) . ?
Cu1 N4 2.0022(17) 2_756 ?
Cu1 N1 2.004(2) . ?
Cu1 N1 2.004(2) 2_756 ?
N4 C4 1.385(3) . ?
N4 C3 1.318(3) . ?
N1 C1 1.153(3) . ?
N2 C2 1.316(3) . ?
N2 C1 1.303(3) . ?
N5 C3 1.356(3) . ?
N5 C5 1.377(3) . ?
N5 C6 1.417(3) . ?
N3 C2 1.152(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.350(3) . ?
C3 H3 0.9500 . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C6 C7 1.318(3) . ?
C7 H7A 1.01(3) . ?
C7 H7B 1.00(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
N4 Cu1 N4 180.0 . 2_756 ?
N4 Cu1 N1 90.19(7) . 2_756 ?
N4 Cu1 N1 89.81(7) 2_756 2_756 ?
N4 Cu1 N1 89.81(7) . . ?
N4 Cu1 N1 90.19(7) 2_756 . ?
N1 Cu1 N1 180.0 2_756 . ?
C4 N4 Cu1 127.90(16) . . ?
C3 N4 Cu1 125.86(15) . . ?
C3 N4 C4 106.19(18) . . ?
C1 N1 Cu1 168.92(18) . . ?
C1 N2 C2 120.4(2) . . ?
C3 N5 C5 107.37(19) . . ?
C3 N5 C6 124.2(2) . . ?
C5 N5 C6 128.20(19) . . ?
Cu1 N3 Cu1 0.0 2_766 1_565 ?
C2 N3 Cu1 139.57(17) . 1_565 ?
C2 N3 Cu1 139.57(17) . 2_766 ?
N3 C2 N2 173.4(2) . . ?
N4 C4 H4 125.3 . . ?
C5 C4 N4 109.5(2) . . ?
C5 C4 H4 125.3 . . ?
N4 C3 N5 110.6(2) . . ?
N4 C3 H3 124.7 . . ?
N5 C3 H3 124.7 . . ?
N5 C5 H5 126.8 . . ?
C4 C5 N5 106.35(19) . . ?
C4 C5 H5 126.8 . . ?
N1 C1 N2 173.5(2) . . ?
N5 C6 H6 117.9 . . ?
C7 C6 N5 124.2(2) . . ?
C7 C6 H6 117.9 . . ?
C6 C7 H7A 118.6(17) . . ?
C6 C7 H7B 123.6(17) . . ?
H7A C7 H7B 118(2) . . ?

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
Cu1 N4 C4 C5 -177.24(15) . . . . ?
Cu1 N4 C3 N5 177.83(14) . . . . ?
N4 C4 C5 N5 -0.7(3) . . . . ?
C4 N4 C3 N5 0.2(3) . . . . ?
C3 N4 C4 C5 0.3(3) . . . . ?
C3 N5 C5 C4 0.8(3) . . . . ?
C3 N5 C6 C7 174.9(2) . . . . ?
C5 N5 C3 N4 -0.7(3) . . . . ?
C5 N5 C6 C7 1.3(4) . . . . ?
C6 N5 C3 N4 -175.3(2) . . . . ?
C6 N5 C5 C4 175.2(2) . . . . ?

_shelx_res_file                  
;
TITL bhy-170_auto_a.res in P-1
    bhy-170_auto.res
    created by SHELXL-2016/6 at 11:26:39 on 02-Oct-2022
REM Old TITL bhy-170_auto_a.res in P-1
REM SHELXT solution in P-1: R1 0.088, Rweak 0.020, Alpha 0.022
REM <I/s> 0.000 for 0 systematic absences, Orientation as input
REM Formula found by SHELXT: C16 Cu N8
CELL 0.71073 6.5089 7.4005 8.7801 105.113 96.853 95.783
ZERR 1 0.0003 0.0004 0.0004 0.004 0.004 0.004
LATT 1
SFAC C H Cu N
UNIT 14 12 1 10
EQIV $1 +X,1+Y,+Z
EQIV $2 2-X,1-Y,1-Z

L.S. 20
PLAN  5
TEMP -173
CONF
BIND N3 Cu1_$1
BIND N3 Cu1_$2
BOND
list 4
MORE -1
BOND $H
fmap 2 53
acta
REM <olex2.extras>
REM <HklSrc "%.\\bhy-170_auto.hkl">
REM </olex2.extras>

WGHT    0.044700    0.108700
FVAR       1.13669
CU1   3    1.000000    0.000000    0.500000    10.50000    0.01536    0.01163 =
         0.01424   -0.00099   -0.00142    0.00307
N4    4    0.801150   -0.119739    0.297953    11.00000    0.01472    0.01330 =
         0.01381    0.00214    0.00105    0.00156
N1    4    0.830482    0.213527    0.550797    11.00000    0.01798    0.01367 =
         0.01777    0.00130   -0.00185    0.00293
N2    4    0.669595    0.495940    0.659271    11.00000    0.02385    0.01329 =
         0.02252    0.00322    0.00984    0.00642
N5    4    0.520724   -0.183266    0.116387    11.00000    0.01360    0.01469 =
         0.01333    0.00229   -0.00059   -0.00055
N3    4    0.770984    0.815815    0.634731    11.00000    0.01886    0.01610 =
         0.01839    0.00232    0.00148    0.00247
C2    1    0.729922    0.662879    0.640324    11.00000    0.01264    0.01776 =
         0.00959   -0.00035    0.00059    0.00542
C4    1    0.836911   -0.250780    0.162611    11.00000    0.01584    0.01523 =
         0.01571    0.00047    0.00316    0.00100
AFIX  43
H4    2    0.962333   -0.304967    0.150800    11.00000   -1.20000
AFIX   0
C3    1    0.609733   -0.081911    0.265916    11.00000    0.01706    0.01386 =
         0.01283    0.00083    0.00161   -0.00048
AFIX  43
H3    2    0.543312    0.004410    0.337648    11.00000   -1.20000
AFIX   0
C5    1    0.665983   -0.289617    0.050050    11.00000    0.01754    0.01528 =
         0.01377   -0.00067    0.00296    0.00099
AFIX  43
H5    2    0.649258   -0.373647   -0.054227    11.00000   -1.20000
AFIX   0
C1    1    0.760907    0.351090    0.597720    11.00000    0.01502    0.01593 =
         0.01009    0.00342   -0.00275   -0.00169
C6    1    0.321397   -0.164148    0.042664    11.00000    0.01318    0.01690 =
         0.02123    0.00475   -0.00048    0.00094
AFIX  43
H6    2    0.240280   -0.082440    0.104723    11.00000   -1.20000
AFIX   0
C7    1    0.241311   -0.252477   -0.106518    11.00000    0.02108    0.02135 =
         0.02292    0.00646   -0.00437   -0.00223
H7A   2    0.096981   -0.230285   -0.148998    11.00000    0.03744
H7B   2    0.315562   -0.339547   -0.181167    11.00000    0.03688
HKLF 4




REM  bhy-170_auto_a.res in P-1
REM R1 =  0.0356 for    1570 Fo > 4sig(Fo)  and  0.0414 for all    1736 data
REM    123 parameters refined using      0 restraints

END

WGHT      0.0447      0.1087

REM Highest difference peak  0.392,  deepest hole -0.596,  1-sigma level  0.081
Q1    1   1.0379 -0.0195  0.6323  11.00000  0.05    0.39
Q2    1   0.8489 -0.1447  0.4032  11.00000  0.05    0.35
Q3    1   0.9544  0.1563  0.5265  11.00000  0.05    0.34
Q4    1   0.8261 -0.1840  0.2233  11.00000  0.05    0.32
Q5    1   0.8455  0.2120  0.4626  11.00000  0.05    0.30
;
_shelx_res_checksum              30573
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_bhy-cd-2_auto
_database_code_depnum_ccdc_archive 'CCDC 2219269'
loop_
_audit_author_name
_audit_author_address
'hongyi Bian'
;fjirsm
China
;
_audit_update_record             
;
2022-11-12 deposited with the CCDC.	2023-08-06 downloaded from the CCDC.
;
_audit_creation_date             2022-10-02
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            '[Cd(VIM)2(DCA)2]n'
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H6 Cd0.5 N5'
_chemical_formula_sum            'C7 H6 Cd0.50 N5'
_chemical_formula_weight         216.37
_chemical_melting_point          ?
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 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -0.8075 1.2024 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.5492(2)
_cell_length_b                   7.5459(3)
_cell_length_c                   8.8473(4)
_cell_angle_alpha                101.719(3)
_cell_angle_beta                 95.002(3)
_cell_angle_gamma                94.124(3)
_cell_volume                     424.68(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2979
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      28.2640
_cell_measurement_theta_min      2.3390
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.306
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.692
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             214
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_unetI/netI     0.0729
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.812
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4104
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.812
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.928
_diffrn_reflns_theta_min         2.364
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.812
_diffrn_measurement_device_type  'ROD, Synergy Custom DW system, HyPix'
_diffrn_measurement_method       ?
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1765
_reflns_number_total             1823
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         1.021
_refine_diff_density_min         -1.313
_refine_diff_density_rms         0.142
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     115
_refine_ls_number_reflns         1823
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0410
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0369P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.0826
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C4(H4), C6(H6)
2.b X=CH2 refined with riding coordinates:
 C7(H7A,H7B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
Cd1 Cd 0.500000 0.000000 0.000000 0.01920(14) Uani 1 2 d S . P . .
N5 N 0.9866(4) 0.1844(4) 0.3862(3) 0.0185(6) Uani 1 1 d . . . . .
N4 N 0.7137(4) 0.1308(4) 0.2145(3) 0.0193(6) Uani 1 1 d . . . . .
N2 N 0.1607(5) 0.5222(4) 0.1689(4) 0.0300(8) Uani 1 1 d . . . . .
N1 N 0.2793(5) 0.2311(4) 0.0506(4) 0.0252(7) Uani 1 1 d . . . . .
N3 N 0.2997(4) 0.8230(4) 0.1389(3) 0.0226(7) Uani 1 1 d . . . . .
C3 C 0.9019(5) 0.0886(5) 0.2459(4) 0.0195(7) Uani 1 1 d . . . . .
H3 H 0.969369 0.002234 0.178867 0.023 Uiso 1 1 calc R U . . .
C2 C 0.2397(5) 0.6781(5) 0.1467(4) 0.0188(7) Uani 1 1 d . . . . .
C1 C 0.2309(5) 0.3721(5) 0.1021(4) 0.0199(7) Uani 1 1 d . . . . .
C5 C 0.8430(5) 0.2934(5) 0.4485(4) 0.0226(8) Uani 1 1 d . . . . .
H5 H 0.857015 0.375534 0.546364 0.027 Uiso 1 1 calc R U . . .
C4 C 0.6763(6) 0.2591(5) 0.3403(4) 0.0223(8) Uani 1 1 d . . . . .
H4 H 0.551958 0.315905 0.350411 0.027 Uiso 1 1 calc R U . . .
C6 C 1.1853(5) 0.1625(5) 0.4550(4) 0.0221(8) Uani 1 1 d . . . . .
H6 H 1.269417 0.084366 0.395052 0.027 Uiso 1 1 calc R U . . .
C7 C 1.2588(6) 0.2443(5) 0.5967(4) 0.0282(9) Uani 1 1 d . . . . .
H7A H 1.178088 0.323227 0.659276 0.034 Uiso 1 1 calc R U . . .
H7B H 1.392734 0.224700 0.636787 0.034 Uiso 1 1 calc R U . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cd1 0.0231(2) 0.0109(2) 0.0226(2) 0.00089(14) 0.00089(14) 0.00398(14)
N5 0.0208(16) 0.0137(15) 0.0208(15) 0.0035(12) 0.0018(12) 0.0005(12)
N4 0.0238(16) 0.0135(15) 0.0203(14) 0.0017(12) 0.0030(12) 0.0042(12)
N2 0.044(2) 0.0117(15) 0.0359(18) 0.0008(14) 0.0222(15) 0.0044(14)
N1 0.0266(17) 0.0131(16) 0.0359(18) 0.0019(13) 0.0070(13) 0.0065(13)
N3 0.0277(17) 0.0153(16) 0.0254(16) 0.0037(13) 0.0049(13) 0.0040(13)
C3 0.0242(19) 0.0135(17) 0.0200(17) 0.0011(14) 0.0041(14) 0.0017(14)
C2 0.0203(18) 0.0179(19) 0.0182(17) -0.0002(14) 0.0054(14) 0.0085(14)
C1 0.0206(19) 0.0185(19) 0.0210(17) 0.0066(15) 0.0012(14) -0.0005(14)
C5 0.025(2) 0.0179(19) 0.0237(18) -0.0002(15) 0.0065(15) 0.0021(15)
C4 0.0250(19) 0.0171(18) 0.0243(18) 0.0010(15) 0.0057(15) 0.0047(14)
C6 0.0198(19) 0.0174(18) 0.0298(19) 0.0073(15) 0.0010(15) 0.0008(14)
C7 0.027(2) 0.025(2) 0.031(2) 0.0070(17) -0.0024(16) 0.0001(16)

_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
Cd1 N4 2.261(3) . ?
Cd1 N4 2.261(3) 2_655 ?
Cd1 N1 2.343(3) 2_655 ?
Cd1 N1 2.343(3) . ?
Cd1 N3 2.390(3) 2_665 ?
Cd1 N3 2.390(3) 1_545 ?
N5 C3 1.352(4) . ?
N5 C5 1.372(4) . ?
N5 C6 1.423(4) . ?
N4 C3 1.315(4) . ?
N4 C4 1.371(4) . ?
N2 C2 1.310(4) . ?
N2 C1 1.301(5) . ?
N1 C1 1.148(4) . ?
N3 C2 1.152(4) . ?
C3 H3 0.9500 . ?
C5 H5 0.9500 . ?
C5 C4 1.361(5) . ?
C4 H4 0.9500 . ?
C6 H6 0.9500 . ?
C6 C7 1.313(5) . ?
C7 H7A 0.9500 . ?
C7 H7B 0.9500 . ?

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
N4 Cd1 N4 180.0 . 2_655 ?
N4 Cd1 N1 91.10(11) 2_655 2_655 ?
N4 Cd1 N1 88.90(11) 2_655 . ?
N4 Cd1 N1 88.90(11) . 2_655 ?
N4 Cd1 N1 91.10(11) . . ?
N4 Cd1 N3 92.74(10) 2_655 2_665 ?
N4 Cd1 N3 87.26(10) 2_655 1_545 ?
N4 Cd1 N3 92.74(10) . 1_545 ?
N4 Cd1 N3 87.26(10) . 2_665 ?
N1 Cd1 N1 180.0 2_655 . ?
N1 Cd1 N3 89.65(10) 2_655 2_665 ?
N1 Cd1 N3 89.65(10) . 1_545 ?
N1 Cd1 N3 90.35(10) 2_655 1_545 ?
N1 Cd1 N3 90.35(10) . 2_665 ?
N3 Cd1 N3 180.00(13) 2_665 1_545 ?
C3 N5 C5 107.5(3) . . ?
C3 N5 C6 124.1(3) . . ?
C5 N5 C6 128.2(3) . . ?
C3 N4 Cd1 125.2(2) . . ?
C3 N4 C4 105.7(3) . . ?
C4 N4 Cd1 129.1(2) . . ?
C1 N2 C2 119.7(3) . . ?
C1 N1 Cd1 157.3(3) . . ?
C2 N3 Cd1 145.2(3) . 1_565 ?
N5 C3 H3 124.4 . . ?
N4 C3 N5 111.1(3) . . ?
N4 C3 H3 124.4 . . ?
N3 C2 N2 173.5(4) . . ?
N1 C1 N2 173.2(4) . . ?
N5 C5 H5 127.3 . . ?
C4 C5 N5 105.4(3) . . ?
C4 C5 H5 127.3 . . ?
N4 C4 H4 124.9 . . ?
C5 C4 N4 110.2(3) . . ?
C5 C4 H4 124.9 . . ?
N5 C6 H6 118.2 . . ?
C7 C6 N5 123.6(4) . . ?
C7 C6 H6 118.2 . . ?
C6 C7 H7A 120.0 . . ?
C6 C7 H7B 120.0 . . ?
H7A C7 H7B 120.0 . . ?

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
Cd1 N4 C3 N5 -177.0(2) . . . . ?
Cd1 N4 C4 C5 176.4(2) . . . . ?
N5 C5 C4 N4 0.6(4) . . . . ?
C3 N5 C5 C4 -0.6(4) . . . . ?
C3 N5 C6 C7 -173.7(3) . . . . ?
C3 N4 C4 C5 -0.4(4) . . . . ?
C5 N5 C3 N4 0.4(4) . . . . ?
C5 N5 C6 C7 2.2(5) . . . . ?
C4 N4 C3 N5 0.0(4) . . . . ?
C6 N5 C3 N4 177.1(3) . . . . ?
C6 N5 C5 C4 -177.1(3) . . . . ?

_shelx_res_file                  
;
TITL bhy-cd-2_auto_a.res in P-1
    bhy-cd-2_auto.res
    created by SHELXL-2016/6 at 12:27:04 on 02-Oct-2022
REM Old TITL bhy-Cd-2_auto in P1
REM SHELXT solution in P-1
REM R1 0.103, Rweak 0.097, Alpha 0.083, Orientation as input
REM Formula found by SHELXT: C18 N6 Br
CELL 0.71073 6.5492 7.5459 8.8473 101.719 95.002 94.124
ZERR 2 0.0002 0.0003 0.0004 0.003 0.003 0.003
LATT 1
SFAC C H Cd N
UNIT 14 12 1 10

L.S. 4 0 0
PLAN  5
TEMP -173
CONF
BOND $H
list 4
MORE -1
fmap 2 53
acta
REM <olex2.extras>
REM <HklSrc "%.\\bhy-cd-2_auto.hkl">
REM </olex2.extras>

WGHT    0.036900
FVAR       0.98462
CD1   3    0.500000    0.000000    0.000000    10.50000    0.02311    0.01087 =
         0.02259    0.00089    0.00089    0.00398
N5    4    0.986616    0.184413    0.386192    11.00000    0.02077    0.01375 =
         0.02078    0.00355    0.00181    0.00052
N4    4    0.713665    0.130767    0.214503    11.00000    0.02384    0.01354 =
         0.02031    0.00167    0.00296    0.00419
N2    4    0.160682    0.522160    0.168886    11.00000    0.04407    0.01167 =
         0.03593    0.00081    0.02223    0.00439
N1    4    0.279345    0.231092    0.050630    11.00000    0.02656    0.01312 =
         0.03592    0.00189    0.00698    0.00647
N3    4    0.299720    0.822957    0.138913    11.00000    0.02766    0.01533 =
         0.02538    0.00368    0.00490    0.00398
C3    1    0.901856    0.088625    0.245919    11.00000    0.02418    0.01353 =
         0.01998    0.00107    0.00406    0.00174
AFIX  43
H3    2    0.969369    0.002234    0.178867    11.00000   -1.20000
AFIX   0
C2    1    0.239703    0.678136    0.146716    11.00000    0.02026    0.01794 =
         0.01817   -0.00021    0.00535    0.00854
C1    1    0.230896    0.372148    0.102074    11.00000    0.02061    0.01854 =
         0.02100    0.00663    0.00124   -0.00054
C5    1    0.843026    0.293446    0.448453    11.00000    0.02480    0.01792 =
         0.02373   -0.00017    0.00648    0.00209
AFIX  43
H5    2    0.857015    0.375534    0.546364    11.00000   -1.20000
AFIX   0
C4    1    0.676326    0.259109    0.340260    11.00000    0.02500    0.01705 =
         0.02435    0.00102    0.00575    0.00471
AFIX  43
H4    2    0.551958    0.315905    0.350411    11.00000   -1.20000
AFIX   0
C6    1    1.185348    0.162495    0.454986    11.00000    0.01976    0.01743 =
         0.02978    0.00734    0.00095    0.00080
AFIX  43
H6    2    1.269417    0.084366    0.395052    11.00000   -1.20000
AFIX   0
C7    1    1.258824    0.244346    0.596739    11.00000    0.02728    0.02510 =
         0.03147    0.00700   -0.00236    0.00010
AFIX  93
H7A   2    1.178088    0.323227    0.659276    11.00000   -1.20000
H7B   2    1.392734    0.224700    0.636787    11.00000   -1.20000
AFIX   0
HKLF 4




REM  bhy-cd-2_auto_a.res in P-1
REM R1 =  0.0410 for    1765 Fo > 4sig(Fo)  and  0.0430 for all    1823 data
REM    115 parameters refined using      0 restraints

END

WGHT      0.0369      0.0000

REM Highest difference peak  1.021,  deepest hole -1.313,  1-sigma level  0.142
Q1    1   0.3946 -0.0005  0.0671  11.00000  0.05    0.95
Q2    1   0.4643  0.0363 -0.0949  11.00000  0.05    0.93
Q3    1   0.4578 -0.0788  0.0630  11.00000  0.05    0.85
Q4    1   0.5274  0.2466  0.0464  11.00000  0.05    0.59
Q5    1   0.2808 -0.0480  0.0205  11.00000  0.05    0.58
;
_shelx_res_checksum              67699
_olex2_submission_special_instructions 'No special instructions were received'
