# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_Ide002
_database_code_depnum_ccdc_archive 'CCDC 2053635'
loop_
_audit_author_name
_audit_author_address
'Tomohito Ide'
;National Insitute of Technology, Tokyo College
Japan
;
_audit_update_record             
;
2021-01-04 deposited with the CCDC.	2021-06-08 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C10 H8 Br2 Cl2 Cu2 N2'
_chemical_formula_moiety         'C10 H8 Br2 Cl2 Cu2 N2'
_chemical_formula_weight         513.99
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   3.836(3)
_cell_length_b                   8.624(7)
_cell_length_c                   10.449(9)
_cell_angle_alpha                103.776(12)
_cell_angle_beta                 93.709(14)
_cell_angle_gamma                90.104(12)
_cell_volume                     335.0(5)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1132
_cell_measurement_theta_min      3.51
_cell_measurement_theta_max      27.46
_cell_measurement_temperature    113
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.147
_exptl_crystal_size_mid          0.049
_exptl_crystal_size_min          0.006
_exptl_crystal_density_diffrn    2.548
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             244.00
_exptl_absorpt_coefficient_mu    9.533
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.340
_exptl_absorpt_correction_T_max  0.944

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      113
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Saturn70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.314
_diffrn_reflns_number            2680
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_theta_max         27.489
_diffrn_reflns_theta_min         3.508
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             1464
_reflns_number_gt                1156
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0329
_refine_ls_wR_factor_ref         0.0895
_refine_ls_wR_factor_gt          0.0881
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         1464
_refine_ls_number_parameters     82
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0356P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         1.09
_refine_diff_density_min         -0.89
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
Br Br -0.2901 2.4595
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cu Cu 0.3201 1.2651
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.13442(13) 0.23459(6) 0.45101(5) 0.01281(16) Uani 1 1 d . . . . .
Cu1 Cu 0.71677(18) 0.01232(8) 0.89199(7) 0.0179(2) Uani 1 1 d . . . . .
Cl1 Cl 1.1957(3) -0.15000(14) 0.86497(12) 0.0115(3) Uani 1 1 d . . . . .
N1 N 0.6061(11) 0.1928(5) 0.8059(4) 0.0126(9) Uani 1 1 d . . . . .
C1 C 0.4365(13) 0.1639(6) 0.6870(5) 0.0119(11) Uani 1 1 d . . . . .
H1 H 0.3688 0.0574 0.6436 0.014 Uiso 1 1 calc R U . . .
C2 C 0.3570(13) 0.2869(6) 0.6255(5) 0.0103(10) Uani 1 1 d . . . . .
C3 C 0.4459(13) 0.4420(6) 0.6864(5) 0.0127(11) Uani 1 1 d . . . . .
H2 H 0.3913 0.5263 0.6446 0.015 Uiso 1 1 calc R U . . .
C4 C 0.6213(13) 0.4727(6) 0.8130(5) 0.0138(11) Uani 1 1 d . . . . .
H3 H 0.6873 0.5783 0.8594 0.017 Uiso 1 1 calc R U . . .
C5 C 0.6938(13) 0.3447(6) 0.8674(5) 0.0132(11) Uani 1 1 d . . . . .
H4 H 0.8118 0.3647 0.9527 0.016 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
Br1 0.0112(3) 0.0160(3) 0.0116(3) 0.0047(2) -0.0018(2) -0.0002(2)
Cu1 0.0197(4) 0.0149(4) 0.0205(4) 0.0081(3) -0.0024(3) 0.0013(3)
Cl1 0.0110(6) 0.0118(6) 0.0116(6) 0.0035(5) -0.0019(5) -0.0003(5)
N1 0.014(2) 0.010(2) 0.014(2) 0.0033(18) 0.0003(18) -0.0018(18)
C1 0.011(3) 0.010(3) 0.013(3) -0.001(2) 0.006(2) 0.001(2)
C2 0.007(3) 0.014(3) 0.010(2) 0.003(2) 0.000(2) -0.001(2)
C3 0.013(3) 0.014(3) 0.014(3) 0.008(2) 0.003(2) 0.001(2)
C4 0.017(3) 0.009(3) 0.014(3) -0.002(2) 0.001(2) 0.002(2)
C5 0.008(3) 0.016(3) 0.015(3) 0.003(2) 0.002(2) -0.001(2)

#==============================================================================
_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL Version 2014/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# 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 C2 1.914(5) . ?
Cu1 N1 2.008(4) . ?
Cu1 Cl1 2.3028(19) . ?
Cu1 Cl1 2.401(2) 1_455 ?
Cu1 Cl1 2.535(2) 2_757 ?
Cu1 Cu1 2.936(2) 2_657 ?
Cl1 Cu1 2.401(2) 1_655 ?
Cl1 Cu1 2.534(2) 2_757 ?
N1 C1 1.333(7) . ?
N1 C5 1.346(6) . ?
C1 C2 1.390(7) . ?
C1 H1 0.9500 . ?
C2 C3 1.369(7) . ?
C3 C4 1.411(7) . ?
C3 H2 0.9500 . ?
C4 C5 1.377(7) . ?
C4 H3 0.9500 . ?
C5 H4 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
N1 Cu1 Cl1 127.39(14) . . ?
N1 Cu1 Cl1 106.77(14) . 1_455 ?
Cl1 Cu1 Cl1 109.27(8) . 1_455 ?
N1 Cu1 Cl1 103.36(14) . 2_757 ?
Cl1 Cu1 Cl1 101.21(5) . 2_757 ?
Cl1 Cu1 Cl1 107.05(5) 1_455 2_757 ?
N1 Cu1 Cu1 115.81(13) . 2_657 ?
Cl1 Cu1 Cu1 115.96(6) . 2_657 ?
Cl1 Cu1 Cu1 55.62(5) 1_455 2_657 ?
Cl1 Cu1 Cu1 51.43(5) 2_757 2_657 ?
Cu1 Cl1 Cu1 109.27(8) . 1_655 ?
Cu1 Cl1 Cu1 78.79(5) . 2_757 ?
Cu1 Cl1 Cu1 72.95(5) 1_655 2_757 ?
C1 N1 C5 118.7(4) . . ?
C1 N1 Cu1 120.1(4) . . ?
C5 N1 Cu1 121.2(4) . . ?
N1 C1 C2 121.1(5) . . ?
N1 C1 H1 119.5 . . ?
C2 C1 H1 119.5 . . ?
C3 C2 C1 120.9(5) . . ?
C3 C2 Br1 120.4(4) . . ?
C1 C2 Br1 118.6(4) . . ?
C2 C3 C4 117.9(5) . . ?
C2 C3 H2 121.1 . . ?
C4 C3 H2 121.1 . . ?
C5 C4 C3 118.0(5) . . ?
C5 C4 H3 121.0 . . ?
C3 C4 H3 121.0 . . ?
N1 C5 C4 123.3(5) . . ?
N1 C5 H4 118.3 . . ?
C4 C5 H4 118.3 . . ?

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
C5 N1 C1 C2 1.4(7) . . . . ?
Cu1 N1 C1 C2 180.0(4) . . . . ?
N1 C1 C2 C3 -1.1(8) . . . . ?
N1 C1 C2 Br1 176.8(4) . . . . ?
C1 C2 C3 C4 0.2(8) . . . . ?
Br1 C2 C3 C4 -177.7(4) . . . . ?
C2 C3 C4 C5 0.3(7) . . . . ?
C1 N1 C5 C4 -0.9(8) . . . . ?
Cu1 N1 C5 C4 -179.5(4) . . . . ?
C3 C4 C5 N1 0.0(8) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

_shelxl_version_number           2014-3

_shelx_res_file                  
;
TITL Ide002
CELL  0.71075 3.83630 8.62420 10.44870 103.77610 93.70890 90.10430
ZERR  1 0.00290 0.00700 0.00860 0.01160 0.01350 0.01230
LATT 1
SFAC C H BR CU N CL
UNIT 50 40 10 10 10 10
L.S. 10
FMAP 2
PLAN 50
WPDB -2
HTAB
BOND $H
CONF
LIST 4
TEMP -159.8
ACTA
SIZE 0.200 0.200 0.200
WGHT    0.035600
FVAR       1.12928
BR1   3    0.134420    0.234589    0.451007    11.00000    0.01121    0.01599 =
         0.01158    0.00469   -0.00185   -0.00022
CU1   4    0.716771    0.012321    0.891989    11.00000    0.01967    0.01493 =
         0.02048    0.00809   -0.00239    0.00129
CL1   6    1.195658   -0.149997    0.864972    11.00000    0.01098    0.01181 =
         0.01165    0.00353   -0.00186   -0.00026
N1    5    0.606093    0.192844    0.805908    11.00000    0.01352    0.01012 =
         0.01422    0.00326    0.00029   -0.00181
C1    1    0.436499    0.163890    0.687023    11.00000    0.01088    0.01008 =
         0.01346   -0.00110    0.00640    0.00143
AFIX  43
H1    2    0.368787    0.057388    0.643571    11.00000   -1.20000
AFIX   0
C2    1    0.357037    0.286909    0.625547    11.00000    0.00698    0.01363 =
         0.01015    0.00261    0.00024   -0.00068
C3    1    0.445932    0.441995    0.686362    11.00000    0.01271    0.01416 =
         0.01413    0.00830    0.00283    0.00142
AFIX  43
H2    2    0.391314    0.526294    0.644614    11.00000   -1.20000
AFIX   0
C4    1    0.621263    0.472653    0.813027    11.00000    0.01666    0.00861 =
         0.01388   -0.00171    0.00063    0.00223
AFIX  43
H3    2    0.687253    0.578339    0.859385    11.00000   -1.20000
AFIX   0
C5    1    0.693808    0.344732    0.867399    11.00000    0.00771    0.01636 =
         0.01503    0.00264    0.00155   -0.00060
AFIX  43
H4    2    0.811777    0.364712    0.952655    11.00000   -1.20000
AFIX   0
HKLF 4

REM  Ide002
REM R1 =  0.0329 for    1156 Fo > 4sig(Fo)  and  0.0393 for all    1464 data
REM     82 parameters refined using      0 restraints

END

WGHT      0.0351      0.0000

REM Instructions for potential hydrogen bonds
EQIV $1 -x+1, -y+1, -z+1
HTAB C3 Br1_$1
EQIV $2 -x+2, -y, -z+2
HTAB C5 Cl1_$2

REM Highest difference peak  1.088,  deepest hole -0.891,  1-sigma level  0.195
Q1    1   0.7269  0.1346  0.9018  11.00000  0.05    1.09
Q2    1   0.7183  0.7161  0.8847  11.00000  0.05    0.96
Q3    1  -0.1405  0.3440  0.5378  11.00000  0.05    0.79
Q4    1   1.3680 -0.1386  0.9857  11.00000  0.05    0.68
Q5    1   1.1729  0.0439  0.9210  11.00000  0.05    0.66
Q6    1   1.0623  0.5998  0.7870  11.00000  0.05    0.65
Q7    1   0.5175  0.2676  0.4722  11.00000  0.05    0.65
Q8    1   0.2168  0.2640  0.8896  11.00000  0.05    0.64
Q9    1  -0.1316  0.1862  0.5517  11.00000  0.05    0.64
Q10   1   0.1086 -0.0819  0.6451  11.00000  0.05    0.61
Q11   1   0.1570  0.4766  0.8493  11.00000  0.05    0.60
Q12   1   1.1556 -0.1226  0.7160  11.00000  0.05    0.59
Q13   1   0.3839  0.0632  0.7016  11.00000  0.05    0.59
Q14   1   0.1706 -0.0439  0.6568  11.00000  0.05    0.58
Q15   1   0.2687  0.2399  0.6668  11.00000  0.05    0.57
Q16   1   0.5268  0.4302  0.5651  11.00000  0.05    0.55
Q17   1   0.4408  0.3457  0.6368  11.00000  0.05    0.53
Q18   1   0.3977 -0.0217  0.8664  11.00000  0.05    0.53
Q19   1   0.4837  0.1510  0.6579  11.00000  0.05    0.53
Q20   1   0.7684  0.2372  1.0131  11.00000  0.05    0.52
Q21   1   0.1467  0.1275  0.3929  11.00000  0.05    0.52
Q22   1   1.2688 -0.2717  0.7468  11.00000  0.05    0.50
Q23   1   0.3118  0.2502  0.5648  11.00000  0.05    0.49
Q24   1   0.3503  0.5960  0.5153  11.00000  0.05    0.48
Q25   1   0.9468  0.3666  0.9550  11.00000  0.05    0.48
Q26   1   0.9604 -0.0803  0.8717  11.00000  0.05    0.47
Q27   1   1.4335 -0.1624  0.7770  11.00000  0.05    0.47
Q28   1   0.1655  0.3206  0.5244  11.00000  0.05    0.47
Q29   1   0.3749  0.2329  0.9320  11.00000  0.05    0.46
Q30   1   0.7840  0.4209  0.9400  11.00000  0.05    0.46
Q31   1   0.0116  0.2791  0.5774  11.00000  0.05    0.46
Q32   1   0.7952  0.4600  1.0186  11.00000  0.05    0.46
Q33   1   0.3092  0.5029  0.5224  11.00000  0.05    0.45
Q34   1   0.8887  0.0283  0.9634  11.00000  0.05    0.44
Q35   1   0.6567  0.3597  0.9769  11.00000  0.05    0.43
Q36   1   0.5053  0.1777  0.5669  11.00000  0.05    0.43
Q37   1   0.2747  0.6453  0.7524  11.00000  0.05    0.43
Q38   1   0.1697  0.1275  0.6403  11.00000  0.05    0.42
Q39   1   0.8008  0.4964  0.7422  11.00000  0.05    0.42
Q40   1  -0.2311  0.1834  0.4134  11.00000  0.05    0.42
Q41   1   0.8859  0.5822  0.8975  11.00000  0.05    0.42
Q42   1   0.7162  0.0398  1.0218  11.00000  0.05    0.42
Q43   1   0.7446  0.1165  0.6658  11.00000  0.05    0.42
Q44   1   1.0639  0.3031  0.8443  11.00000  0.05    0.41
Q45   1   0.6162  0.5365  0.8416  11.00000  0.05    0.41
Q46   1   0.2230  0.1049  0.2906  11.00000  0.05    0.40
Q47   1   0.3426  0.1603  0.4361  11.00000  0.05    0.40
Q48   1   0.0999  0.0669  0.5328  11.00000  0.05    0.39
Q49   1   0.7227 -0.0756  0.8114  11.00000  0.05    0.39
Q50   1   1.1750 -0.0633  0.9304  11.00000  0.05    0.38
;

_shelx_res_checksum              79048
####################################################################### 
# 
# 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_hy322
_database_code_depnum_ccdc_archive 'CCDC 2053632'
loop_
_audit_author_name
_audit_author_address
'Tomohito ide'
;National Institute of Technology, Tokyo College
Japan
;
_audit_update_record             
;
2021-03-13 deposited with the CCDC.	2021-06-08 downloaded from the CCDC.
;
_audit_creation_date             2021-03-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H14 Cl2 Cu2 N2 O2'
_chemical_formula_sum            'C12 H14 Cl2 Cu2 N2 O2'
_chemical_formula_weight         416.23
_chemical_absolute_configuration ?
_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 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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      orthorhombic
_space_group_IT_number           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   17.2967(9)
_cell_length_b                   3.8127(2)
_cell_length_c                   21.4776(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1416.39(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2544
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      73.9340
_cell_measurement_theta_min      5.5290
_shelx_estimated_absorpt_T_max   0.693
_shelx_estimated_absorpt_T_min   0.198
_exptl_absorpt_coefficient_mu    7.191
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.73872
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.952
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.333
_exptl_crystal_size_mid          0.082
_exptl_crystal_size_min          0.055
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_av_unetI/netI     0.0380
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            4323
_diffrn_reflns_point_group_measured_fraction_full 0.763
_diffrn_reflns_point_group_measured_fraction_max 0.713
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.002
_diffrn_reflns_theta_min         4.117
_diffrn_ambient_temperature      90
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -110.00 -83.00   0.50    0.05    --  -46.57-136.00 -47.00   54
  2  ω    -23.00  61.00   0.50    0.05    --   46.57 -57.00  60.00  168
  3  ω     50.00  85.00   0.50    0.21    --  104.61-136.00 -47.00   70
  4  ω     90.00 116.00   0.50    0.21    --  104.61-136.00 -47.00   52
  5  ω     -5.00  26.00   0.50    0.05    --   46.57 -19.00  90.00   62
  6  ω    -42.00 -17.00   0.50    0.05    --  -46.57   4.00  -1.00   50
  7  ω    -63.00 -38.00   0.50    0.21    -- -102.00  61.00 -30.00   50
  8  ω    -61.00 -35.00   0.50    0.21    -- -102.00  61.00-120.00   52
  9  ω    -68.00 -32.00   0.50    0.21    -- -102.00  61.00-180.00   72
 10  ω   -170.00 -59.00   0.50    0.21    -- -102.00  -4.00-178.00  222
 11  ω    145.00 170.00   0.50    0.21    --  104.61 143.00 -77.00   50
 12  ω    104.00 130.00   0.50    0.21    --  104.61 143.00 -77.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0001732000
_diffrn_orient_matrix_UB_12      0.0857912000
_diffrn_orient_matrix_UB_13      0.0193280000
_diffrn_orient_matrix_UB_21      0.0235885000
_diffrn_orient_matrix_UB_22      -0.0239913000
_diffrn_orient_matrix_UB_23      0.0689574000
_diffrn_orient_matrix_UB_31      0.4032405000
_diffrn_orient_matrix_UB_32      0.0014171000
_diffrn_orient_matrix_UB_33      -0.0040551000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.457
_reflns_Friedel_fraction_full    0.511
_reflns_Friedel_fraction_max     0.460
_reflns_number_gt                1946
_reflns_number_total             2101
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.717
_refine_diff_density_rms         0.104
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.47(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     184
_refine_ls_number_reflns         2101
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0359
_refine_ls_R_factor_gt           0.0331
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0532P)²+0.2592P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0913
_refine_ls_wR_factor_ref         0.0942
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.53(4)
 0.47(4)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C4(H4), C7(H7), C9(H9), C5(H5), C1(H1), C11(H11), C10(H10), C3(H3)
3.b Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.56331(4) 1.00810(16) 0.53057(4) 0.0205(3) Uani 1 1 d . . . . .
Cu2 Cu 0.68917(4) 0.49233(16) 0.52148(5) 0.0206(3) Uani 1 1 d . . . . .
Cl2 Cl 0.68954(6) 0.9689(3) 0.58643(8) 0.0158(4) Uani 1 1 d . . . . .
Cl1 Cl 0.56156(6) 0.5245(2) 0.46600(9) 0.0157(4) Uani 1 1 d . . . . .
O2 O 0.7718(2) 0.4815(8) 0.2869(3) 0.0208(9) Uani 1 1 d . . . . .
O1 O 0.4780(2) 0.9469(9) 0.7645(3) 0.0209(9) Uani 1 1 d . . . . .
C12 C 0.8199(3) 0.3865(15) 0.2350(3) 0.0264(11) Uani 1 1 d . . . . .
H12A H 0.798766 0.488540 0.196782 0.040 Uiso 1 1 calc R U . . .
H12B H 0.821478 0.130551 0.231116 0.040 Uiso 1 1 calc R U . . .
H12C H 0.872402 0.475748 0.241839 0.040 Uiso 1 1 calc R U . . .
N1 N 0.4908(2) 1.1165(10) 0.6006(3) 0.0171(8) Uani 1 1 d . . . . .
N2 N 0.76094(19) 0.3662(9) 0.4521(3) 0.0155(7) Uani 1 1 d . . . . .
C8 C 0.7954(2) 0.3696(11) 0.3444(3) 0.0169(8) Uani 1 1 d . . . . .
C4 C 0.3713(2) 1.3650(12) 0.6365(3) 0.0192(9) Uani 1 1 d . . . . .
H4 H 0.325126 1.489166 0.627205 0.023 Uiso 1 1 calc R U . . .
C7 C 0.7461(4) 0.4510(11) 0.3931(4) 0.0175(11) Uani 1 1 d . . . . .
H7 H 0.699609 0.573020 0.383971 0.021 Uiso 1 1 calc R U . . .
C9 C 0.8644(2) 0.1936(11) 0.3566(3) 0.0194(9) Uani 1 1 d . . . . .
H9 H 0.899646 0.138190 0.324149 0.023 Uiso 1 1 calc R U . . .
C5 C 0.4243(2) 1.2944(11) 0.5900(3) 0.0173(8) Uani 1 1 d . . . . .
H5 H 0.413646 1.373735 0.548915 0.021 Uiso 1 1 calc R U . . .
C1 C 0.5056(3) 1.0129(10) 0.6584(3) 0.0148(11) Uani 1 1 d . . . . .
H1 H 0.552490 0.891183 0.666515 0.018 Uiso 1 1 calc R U . . .
C11 C 0.8268(2) 0.1898(11) 0.4644(3) 0.0178(8) Uani 1 1 d . . . . .
H11 H 0.837486 0.123453 0.506166 0.021 Uiso 1 1 calc R U . . .
C2 C 0.4545(3) 1.0768(13) 0.7081(3) 0.0158(9) Uani 1 1 d . . . . .
C10 C 0.8796(3) 0.1019(13) 0.4184(3) 0.0201(9) Uani 1 1 d . . . . .
H10 H 0.925741 -0.019822 0.428735 0.024 Uiso 1 1 calc R U . . .
C3 C 0.3860(3) 1.2532(11) 0.6969(3) 0.0199(9) Uani 1 1 d . . . . .
H3 H 0.350137 1.296583 0.729504 0.024 Uiso 1 1 calc R U . . .
C6 C 0.4286(3) 1.0148(12) 0.8163(3) 0.0250(13) Uani 1 1 d . . . . .
H6A H 0.377264 0.916911 0.808033 0.037 Uiso 1 1 calc R U . . .
H6B H 0.424411 1.268556 0.822646 0.037 Uiso 1 1 calc R U . . .
H6C H 0.450332 0.905575 0.853698 0.037 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
Cu1 0.0232(6) 0.0229(5) 0.0155(7) -0.0016(3) 0.0023(4) 0.0030(2)
Cu2 0.0233(6) 0.0220(4) 0.0163(8) -0.0017(3) 0.0010(4) 0.0034(2)
Cl2 0.0166(7) 0.0156(5) 0.0152(9) -0.0005(7) -0.0019(4) 0.0004(3)
Cl1 0.0167(7) 0.0155(5) 0.0149(9) -0.0009(6) -0.0008(4) 0.0008(3)
O2 0.0230(18) 0.0267(18) 0.013(2) 0.0006(13) 0.0009(16) 0.0045(12)
O1 0.0189(17) 0.0285(16) 0.015(2) 0.0040(16) 0.0018(16) -0.0003(13)
C12 0.037(3) 0.027(3) 0.015(3) -0.005(2) 0.009(2) 0.006(2)
N1 0.0183(18) 0.0149(17) 0.0183(19) 0.0009(16) -0.0001(15) -0.0024(14)
N2 0.0168(16) 0.0131(16) 0.0166(18) -0.0021(16) -0.0003(15) -0.0025(13)
C8 0.0178(18) 0.017(2) 0.015(2) -0.0029(19) 0.0005(17) -0.0048(18)
C4 0.0156(19) 0.018(2) 0.024(2) -0.0031(19) 0.0003(18) -0.0014(16)
C7 0.016(2) 0.0178(19) 0.019(3) -0.002(2) -0.003(2) 0.0019(18)
C9 0.0160(19) 0.020(2) 0.023(2) -0.0028(19) 0.0018(18) -0.0014(16)
C5 0.0171(18) 0.0163(17) 0.019(2) 0.0009(18) -0.0049(17) -0.0015(16)
C1 0.014(2) 0.017(2) 0.013(3) 0.0013(15) 0.001(2) -0.0011(14)
C11 0.0152(17) 0.0171(18) 0.021(2) 0.0007(18) -0.0005(17) -0.0007(15)
C2 0.0177(19) 0.0154(18) 0.014(2) 0.0013(18) -0.0020(17) -0.0041(17)
C10 0.016(2) 0.021(2) 0.023(3) 0.001(2) -0.0015(18) -0.0013(17)
C3 0.0147(19) 0.021(2) 0.024(2) -0.0042(18) 0.0037(17) -0.0038(16)
C6 0.030(3) 0.031(3) 0.014(3) 0.0035(19) 0.006(2) -0.0015(18)

_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 Cu2 2.8610(9) 1_565 ?
Cu1 Cu2 2.9400(8) . ?
Cu1 Cl2 2.4958(17) . ?
Cu1 Cl1 2.4085(17) 1_565 ?
Cu1 Cl1 2.3073(16) . ?
Cu1 N1 2.002(5) . ?
Cu2 Cl2 2.4349(16) 1_545 ?
Cu2 Cl2 2.2908(17) . ?
Cu2 Cl1 2.5114(17) . ?
Cu2 N2 1.998(5) . ?
O2 C12 1.436(7) . ?
O2 C8 1.370(7) . ?
O1 C2 1.371(7) . ?
O1 C6 1.425(8) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
N1 C5 1.355(6) . ?
N1 C1 1.328(8) . ?
N2 C7 1.333(8) . ?
N2 C11 1.350(5) . ?
C8 C7 1.383(8) . ?
C8 C9 1.393(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.382(7) . ?
C4 C3 1.389(7) . ?
C7 H7 0.9500 . ?
C9 H9 0.9500 . ?
C9 C10 1.397(7) . ?
C5 H5 0.9500 . ?
C1 H1 0.9500 . ?
C1 C2 1.407(8) . ?
C11 H11 0.9500 . ?
C11 C10 1.387(7) . ?
C2 C3 1.384(7) . ?
C10 H10 0.9500 . ?
C3 H3 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?

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 Cu1 Cu2 82.17(2) 1_565 . ?
Cl2 Cu1 Cu2 49.01(4) . . ?
Cl2 Cu1 Cu2 53.55(4) . 1_565 ?
Cl1 Cu1 Cu2 55.62(4) . . ?
Cl1 Cu1 Cu2 118.99(4) . 1_565 ?
Cl1 Cu1 Cu2 121.19(4) 1_565 . ?
Cl1 Cu1 Cu2 56.13(4) 1_565 1_565 ?
Cl1 Cu1 Cl2 109.68(5) 1_565 . ?
Cl1 Cu1 Cl2 104.63(4) . . ?
Cl1 Cu1 Cl1 107.88(9) . 1_565 ?
N1 Cu1 Cu2 113.26(11) . 1_565 ?
N1 Cu1 Cu2 130.69(13) . . ?
N1 Cu1 Cl2 101.50(15) . . ?
N1 Cu1 Cl1 127.47(12) . . ?
N1 Cu1 Cl1 104.83(12) . 1_565 ?
Cu1 Cu2 Cu1 82.17(2) 1_545 . ?
Cl2 Cu2 Cu1 120.81(4) 1_545 . ?
Cl2 Cu2 Cu1 55.33(4) . . ?
Cl2 Cu2 Cu1 118.19(4) . 1_545 ?
Cl2 Cu2 Cu1 55.53(4) 1_545 1_545 ?
Cl2 Cu2 Cl2 107.53(9) . 1_545 ?
Cl2 Cu2 Cl1 104.64(5) . . ?
Cl2 Cu2 Cl1 108.31(5) 1_545 . ?
Cl1 Cu2 Cu1 52.78(4) . 1_545 ?
Cl1 Cu2 Cu1 49.31(3) . . ?
N2 Cu2 Cu1 111.61(10) . 1_545 ?
N2 Cu2 Cu1 132.10(13) . . ?
N2 Cu2 Cl2 130.04(11) . . ?
N2 Cu2 Cl2 103.20(12) . 1_545 ?
N2 Cu2 Cl1 101.77(15) . . ?
Cu2 Cl2 Cu1 75.66(6) . . ?
Cu2 Cl2 Cu1 70.92(5) 1_565 . ?
Cu2 Cl2 Cu2 107.53(9) . 1_565 ?
Cu1 Cl1 Cu1 107.88(9) . 1_545 ?
Cu1 Cl1 Cu2 75.07(5) . . ?
Cu1 Cl1 Cu2 71.08(5) 1_545 . ?
C8 O2 C12 116.6(4) . . ?
C2 O1 C6 116.5(4) . . ?
O2 C12 H12A 109.5 . . ?
O2 C12 H12B 109.5 . . ?
O2 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C5 N1 Cu1 120.6(3) . . ?
C1 N1 Cu1 121.3(3) . . ?
C1 N1 C5 118.1(4) . . ?
C7 N2 Cu2 122.1(3) . . ?
C7 N2 C11 118.0(4) . . ?
C11 N2 Cu2 119.9(3) . . ?
O2 C8 C7 115.4(5) . . ?
O2 C8 C9 125.0(4) . . ?
C7 C8 C9 119.6(5) . . ?
C5 C4 H4 120.2 . . ?
C5 C4 C3 119.6(4) . . ?
C3 C4 H4 120.2 . . ?
N2 C7 C8 123.1(5) . . ?
N2 C7 H7 118.5 . . ?
C8 C7 H7 118.5 . . ?
C8 C9 H9 121.3 . . ?
C8 C9 C10 117.4(4) . . ?
C10 C9 H9 121.3 . . ?
N1 C5 C4 122.5(4) . . ?
N1 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
N1 C1 H1 118.8 . . ?
N1 C1 C2 122.4(5) . . ?
C2 C1 H1 118.8 . . ?
N2 C11 H11 118.8 . . ?
N2 C11 C10 122.4(4) . . ?
C10 C11 H11 118.8 . . ?
O1 C2 C1 115.0(5) . . ?
O1 C2 C3 125.7(4) . . ?
C3 C2 C1 119.3(5) . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.5(4) . . ?
C11 C10 H10 120.2 . . ?
C4 C3 H3 121.0 . . ?
C2 C3 C4 117.9(4) . . ?
C2 C3 H3 121.0 . . ?
O1 C6 H6A 109.5 . . ?
O1 C6 H6B 109.5 . . ?
O1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?

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 N1 C5 C4 177.8(3) . . . . ?
Cu1 N1 C1 C2 -178.1(3) . . . . ?
Cu2 N2 C7 C8 179.3(3) . . . . ?
Cu2 N2 C11 C10 -178.6(3) . . . . ?
O2 C8 C7 N2 -179.0(4) . . . . ?
O2 C8 C9 C10 179.3(4) . . . . ?
O1 C2 C3 C4 -179.6(4) . . . . ?
C12 O2 C8 C7 -177.2(4) . . . . ?
C12 O2 C8 C9 4.6(7) . . . . ?
N1 C1 C2 O1 178.9(4) . . . . ?
N1 C1 C2 C3 0.1(7) . . . . ?
N2 C11 C10 C9 -0.8(7) . . . . ?
C8 C9 C10 C11 -0.5(6) . . . . ?
C7 N2 C11 C10 1.3(6) . . . . ?
C7 C8 C9 C10 1.1(6) . . . . ?
C9 C8 C7 N2 -0.6(7) . . . . ?
C5 N1 C1 C2 1.0(6) . . . . ?
C5 C4 C3 C2 0.7(7) . . . . ?
C1 N1 C5 C4 -1.3(6) . . . . ?
C1 C2 C3 C4 -1.0(7) . . . . ?
C11 N2 C7 C8 -0.6(6) . . . . ?
C3 C4 C5 N1 0.4(7) . . . . ?
C6 O1 C2 C1 178.4(4) . . . . ?
C6 O1 C2 C3 -3.0(7) . . . . ?

_shelx_res_file                  
;
TITL hy322_a.res in Pca2(1)
    hy322.res
    created by SHELXL-2018/3 at 20:18:10 on 13-Mar-2021
REM Old TITL hy322_a.res in Pca2(1)
REM SHELXT solution in Pca2(1): R1 0.105, Rweak 0.001, Alpha 0.006
REM <I/s> 0.461 for 286 systematic absences, Orientation as input
REM Flack x = 0.499 ( 0.018 ) from 579 Parsons' quotients
REM Formula found by SHELXT: C11 Cl3 Cu N3 O
CELL 1.54184 17.2967 3.8127 21.4776 90 90 90
ZERR 4 0.0009 0.0002 0.0011 0 0 0
LATT -1
SYMM -X,-Y,0.5+Z
SYMM 0.5+X,-Y,+Z
SYMM 0.5-X,+Y,0.5+Z
SFAC C H Cl Cu N O
UNIT 48 56 8 8 8 8

L.S. 10
PLAN  1
SIZE 0.055 0.082 0.333
TEMP -183.15
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2
acta
TWIN -1 0 0 0 -1 0 0 0 -1 2
REM <olex2.extras>
REM <HklSrc "%.\\hy322.hkl">
REM </olex2.extras>

WGHT    0.053200    0.259200
BASF   0.47226
FVAR       0.43371
CU1   4    0.563313    1.008096    0.530569    11.00000    0.02318    0.02287 =
         0.01551   -0.00160    0.00231    0.00303
CU2   4    0.689166    0.492327    0.521481    11.00000    0.02332    0.02203 =
         0.01631   -0.00167    0.00102    0.00344
CL2   3    0.689543    0.968901    0.586431    11.00000    0.01661    0.01563 =
         0.01524   -0.00047   -0.00186    0.00043
CL1   3    0.561555    0.524517    0.466000    11.00000    0.01670    0.01554 =
         0.01491   -0.00090   -0.00081    0.00084
O2    6    0.771841    0.481485    0.286869    11.00000    0.02302    0.02672 =
         0.01278    0.00064    0.00090    0.00446
O1    6    0.477981    0.946858    0.764536    11.00000    0.01892    0.02849 =
         0.01532    0.00400    0.00175   -0.00031
C12   1    0.819941    0.386542    0.235035    11.00000    0.03725    0.02698 =
         0.01495   -0.00499    0.00868    0.00551
AFIX 137
H12A  2    0.798766    0.488540    0.196782    11.00000   -1.50000
H12B  2    0.821478    0.130551    0.231116    11.00000   -1.50000
H12C  2    0.872402    0.475748    0.241839    11.00000   -1.50000
AFIX   0
N1    5    0.490772    1.116540    0.600618    11.00000    0.01827    0.01486 =
         0.01827    0.00089   -0.00013   -0.00244
N2    5    0.760937    0.366195    0.452092    11.00000    0.01684    0.01310 =
         0.01658   -0.00214   -0.00029   -0.00245
C8    1    0.795414    0.369573    0.344413    11.00000    0.01782    0.01742 =
         0.01534   -0.00291    0.00053   -0.00479
C4    1    0.371321    1.364955    0.636489    11.00000    0.01557    0.01759 =
         0.02431   -0.00306    0.00031   -0.00137
AFIX  43
H4    2    0.325126    1.489166    0.627205    11.00000   -1.20000
AFIX   0
C7    1    0.746147    0.450996    0.393057    11.00000    0.01599    0.01777 =
         0.01865   -0.00152   -0.00331    0.00188
AFIX  43
H7    2    0.699609    0.573020    0.383971    11.00000   -1.20000
AFIX   0
C9    1    0.864359    0.193634    0.356584    11.00000    0.01596    0.01970 =
         0.02255   -0.00280    0.00181   -0.00143
AFIX  43
H9    2    0.899646    0.138190    0.324149    11.00000   -1.20000
AFIX   0
C5    1    0.424284    1.294409    0.589961    11.00000    0.01708    0.01629 =
         0.01856    0.00092   -0.00488   -0.00153
AFIX  43
H5    2    0.413646    1.373735    0.548915    11.00000   -1.20000
AFIX   0
C1    1    0.505635    1.012925    0.658418    11.00000    0.01438    0.01662 =
         0.01339    0.00129    0.00091   -0.00111
AFIX  43
H1    2    0.552490    0.891183    0.666515    11.00000   -1.20000
AFIX   0
C11   1    0.826838    0.189829    0.464403    11.00000    0.01522    0.01714 =
         0.02117    0.00066   -0.00048   -0.00068
AFIX  43
H11   2    0.837486    0.123453    0.506166    11.00000   -1.20000
AFIX   0
C2    1    0.454525    1.076841    0.708120    11.00000    0.01773    0.01537 =
         0.01428    0.00129   -0.00197   -0.00408
C10   1    0.879584    0.101909    0.418353    11.00000    0.01643    0.02091 =
         0.02299    0.00071   -0.00152   -0.00133
AFIX  43
H10   2    0.925741   -0.019822    0.428735    11.00000   -1.20000
AFIX   0
C3    1    0.386010    1.253236    0.696906    11.00000    0.01471    0.02124 =
         0.02362   -0.00424    0.00374   -0.00380
AFIX  43
H3    2    0.350137    1.296583    0.729504    11.00000   -1.20000
AFIX   0
C6    1    0.428648    1.014774    0.816264    11.00000    0.02981    0.03117 =
         0.01401    0.00354    0.00558   -0.00151
AFIX 137
H6A   2    0.377264    0.916911    0.808033    11.00000   -1.50000
H6B   2    0.424411    1.268556    0.822646    11.00000   -1.50000
H6C   2    0.450332    0.905575    0.853698    11.00000   -1.50000
AFIX   0
HKLF 4




REM  hy322_a.res in Pca2(1)
REM wR2 = 0.0942, GooF = S = 1.081, Restrained GooF = 1.080 for all data
REM R1 = 0.0331 for 1946 Fo > 4sig(Fo) and 0.0359 for all 2101 data
REM 184 parameters refined using 1 restraints

END

WGHT      0.0532      0.2592

REM Highest difference peak  0.399,  deepest hole -0.717,  1-sigma level  0.104
Q1    1   0.6867  0.7423  0.5571  11.00000  0.05    0.40
;
_shelx_res_checksum              19391
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.250
_oxdiff_exptl_absorpt_empirical_full_min 0.586
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.53(4)
2 0.47(4)

####################################################################### 
# 
# 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_hy305
_database_code_depnum_ccdc_archive 'CCDC 2053630'
loop_
_audit_author_name
_audit_author_address
'Tomohito ide'
;National Institute of Technology, Tokyo College
Japan
;
_audit_update_record             
;
2021-03-13 deposited with the CCDC.	2021-06-08 downloaded from the CCDC.
;
_audit_creation_date             2021-03-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H4 Br Cu I N'
_chemical_formula_sum            'C5 H4 Br Cu I N'
_chemical_formula_weight         348.44
_chemical_absolute_configuration ?
_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 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_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                   4.0975(2)
_cell_length_b                   11.5751(6)
_cell_length_c                   16.3426(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     775.11(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2233
_cell_measurement_temperature    90
_cell_measurement_theta_max      74.5140
_cell_measurement_theta_min      2.7390
_shelx_estimated_absorpt_T_max   0.195
_shelx_estimated_absorpt_T_min   0.018
_exptl_absorpt_coefficient_mu    40.559
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.32650
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    2.986
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.518
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_unetI/netI     0.0405
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            2498
_diffrn_reflns_point_group_measured_fraction_full 0.885
_diffrn_reflns_point_group_measured_fraction_max 0.838
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.503
_diffrn_reflns_theta_min         4.681
_diffrn_ambient_temperature      90
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      0.00  29.00   0.50    0.05    --   46.57 -24.00 -68.00   58
  2  ω     39.00  72.00   0.50    0.05    --  104.61 -61.00-150.00   66
  3  ω     38.00  72.00   0.50    0.05    --  104.61 -61.00 -90.00   68
  4  ω     37.00  63.00   0.50    0.05    --  104.61 -61.00 -60.00   52
  5  ω    -24.00  26.00   0.50    0.05    --  -46.57  19.00 150.00  100
  6  ω    -57.00 -31.00   0.50    0.05    -- -102.00  61.00   0.00   52
  7  ω    -56.00 -29.00   0.50    0.05    -- -102.00 128.00 -47.00   54
  8  ω    -54.00 -29.00   0.50    0.05    -- -102.00 100.00-122.00   50
  9  ω    -95.00 -70.00   0.50    0.05    -- -102.00 100.00-122.00   50
 10  ω   -111.00 -67.00   0.50    0.05    -- -102.00 128.00 -47.00   88
 11  ω    -24.00  26.00   0.50    0.05    --  -46.57  19.00-150.00  100
 12  ω   -112.00 -75.00   0.50    0.05    --  -46.57-125.00-150.00   74
 13  ω   -158.00 -93.00   0.50    0.05    -- -102.00 -24.00 -68.00  130
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1140264000
_diffrn_orient_matrix_UB_12      0.0131988000
_diffrn_orient_matrix_UB_13      0.0893734000
_diffrn_orient_matrix_UB_21      -0.0288611000
_diffrn_orient_matrix_UB_22      -0.1322839000
_diffrn_orient_matrix_UB_23      0.0075079000
_diffrn_orient_matrix_UB_31      0.3570211000
_diffrn_orient_matrix_UB_32      -0.0063908000
_diffrn_orient_matrix_UB_33      0.0290828000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.427
_reflns_Friedel_fraction_full    0.704
_reflns_Friedel_fraction_max     0.646
_reflns_number_gt                1308
_reflns_number_total             1329
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.928
_refine_diff_density_min         -1.173
_refine_diff_density_rms         0.239
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.097(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     83
_refine_ls_number_reflns         1329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0315
_refine_ls_restrained_S_all      1.065
_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)+(0.0507P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0789
_refine_ls_wR_factor_ref         0.0792
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.903(11)
 0.097(11)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C1(H1), C4(H4)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
I1 I 0.90953(14) 0.62827(4) 0.58740(3) 0.00915(18) Uani 1 1 d . . . . .
Br1 Br 0.4607(3) 0.19314(8) 0.38807(6) 0.0204(3) Uani 1 1 d . . . . .
Cu1 Cu 0.4240(4) 0.67229(11) 0.48900(8) 0.0108(3) Uani 1 1 d . . . . .
N1 N 0.351(2) 0.5458(6) 0.4032(4) 0.0116(16) Uani 1 1 d . . . . .
C3 C 0.174(3) 0.3727(9) 0.2931(5) 0.016(2) Uani 1 1 d . . . . .
H3 H 0.116496 0.312989 0.255903 0.019 Uiso 1 1 calc R U . . .
C5 C 0.186(3) 0.5715(8) 0.3344(6) 0.016(2) Uani 1 1 d . . . . .
H5 H 0.131552 0.649972 0.324364 0.019 Uiso 1 1 calc R U . . .
C2 C 0.340(3) 0.3485(8) 0.3645(6) 0.014(2) Uani 1 1 d . . . . .
C1 C 0.428(2) 0.4358(8) 0.4179(5) 0.0120(18) Uani 1 1 d . . . . .
H1 H 0.546674 0.416940 0.466077 0.014 Uiso 1 1 calc R U . . .
C4 C 0.092(3) 0.4885(8) 0.2769(5) 0.017(2) Uani 1 1 d . . . . .
H4 H -0.022576 0.509616 0.228712 0.020 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
I1 0.0104(3) 0.0074(3) 0.0096(3) 0.0029(2) -0.0003(2) 0.0004(2)
Br1 0.0279(6) 0.0068(4) 0.0266(5) -0.0025(4) 0.0014(5) 0.0017(4)
Cu1 0.0142(7) 0.0073(6) 0.0108(6) -0.0011(4) -0.0019(6) 0.0009(6)
N1 0.015(4) 0.010(3) 0.010(3) 0.002(3) 0.001(3) 0.003(3)
C3 0.027(6) 0.013(4) 0.007(4) -0.004(3) 0.000(4) -0.008(4)
C5 0.022(6) 0.010(4) 0.015(4) 0.001(4) -0.005(4) 0.002(4)
C2 0.018(5) 0.011(4) 0.011(4) 0.000(3) 0.003(4) -0.003(4)
C1 0.016(5) 0.013(4) 0.008(3) 0.001(3) 0.005(4) -0.004(4)
C4 0.024(6) 0.015(4) 0.011(3) -0.003(3) -0.008(5) -0.003(5)

_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
I1 Cu1 2.6083(15) . ?
I1 Cu1 2.7001(16) 1_655 ?
I1 Cu1 2.6252(13) 4_566 ?
Br1 C2 1.904(10) . ?
Cu1 Cu1 2.7502(17) 4_566 ?
Cu1 Cu1 2.7502(16) 4_466 ?
Cu1 N1 2.049(8) . ?
N1 C5 1.345(12) . ?
N1 C1 1.334(11) . ?
C3 H3 0.9500 . ?
C3 C2 1.380(14) . ?
C3 C4 1.407(14) . ?
C5 H5 0.9500 . ?
C5 C4 1.398(13) . ?
C2 C1 1.383(12) . ?
C1 H1 0.9500 . ?
C4 H4 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
Cu1 I1 Cu1 63.40(3) . 4_566 ?
Cu1 I1 Cu1 101.03(5) . 1_655 ?
Cu1 I1 Cu1 62.17(4) 4_566 1_655 ?
I1 Cu1 I1 118.84(6) . 4_466 ?
I1 Cu1 I1 101.03(5) . 1_455 ?
I1 Cu1 I1 115.56(5) 4_466 1_455 ?
I1 Cu1 Cu1 127.97(7) . 4_466 ?
I1 Cu1 Cu1 128.84(7) 1_455 4_566 ?
I1 Cu1 Cu1 60.25(6) 4_466 4_566 ?
I1 Cu1 Cu1 57.58(3) 1_455 4_466 ?
I1 Cu1 Cu1 58.60(3) . 4_566 ?
I1 Cu1 Cu1 58.00(5) 4_466 4_466 ?
Cu1 Cu1 Cu1 96.31(8) 4_466 4_566 ?
N1 Cu1 I1 113.2(2) . . ?
N1 Cu1 I1 107.4(2) . 4_466 ?
N1 Cu1 I1 99.1(2) . 1_455 ?
N1 Cu1 Cu1 131.7(2) . 4_566 ?
N1 Cu1 Cu1 116.6(2) . 4_466 ?
C5 N1 Cu1 119.1(6) . . ?
C1 N1 Cu1 121.6(6) . . ?
C1 N1 C5 118.7(8) . . ?
C2 C3 H3 121.0 . . ?
C2 C3 C4 118.0(9) . . ?
C4 C3 H3 121.0 . . ?
N1 C5 H5 118.4 . . ?
N1 C5 C4 123.2(9) . . ?
C4 C5 H5 118.4 . . ?
C3 C2 Br1 119.4(7) . . ?
C3 C2 C1 120.9(9) . . ?
C1 C2 Br1 119.6(7) . . ?
N1 C1 C2 121.5(9) . . ?
N1 C1 H1 119.3 . . ?
C2 C1 H1 119.3 . . ?
C3 C4 H4 121.2 . . ?
C5 C4 C3 117.6(9) . . ?
C5 C4 H4 121.2 . . ?

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
Br1 C2 C1 N1 179.3(7) . . . . ?
Cu1 N1 C5 C4 -172.5(8) . . . . ?
Cu1 N1 C1 C2 171.3(7) . . . . ?
N1 C5 C4 C3 0.4(17) . . . . ?
C3 C2 C1 N1 1.4(16) . . . . ?
C5 N1 C1 C2 -0.7(15) . . . . ?
C2 C3 C4 C5 0.3(16) . . . . ?
C1 N1 C5 C4 -0.2(16) . . . . ?
C4 C3 C2 Br1 -179.1(8) . . . . ?
C4 C3 C2 C1 -1.2(16) . . . . ?

_shelx_res_file                  
;
TITL exp_849_a.res in P2(1)2(1)2(1)
    exp_849.res
    created by SHELXL-2018/3 at 20:22:59 on 13-Mar-2021
REM Old TITL exp_849_a.res in P2(1)2(1)2(1)
REM SHELXT solution in P2(1)2(1)2(1): R1 0.061, Rweak 0.026, Alpha 0.002
REM <I/s> 1.585 for 19 systematic absences, Orientation as input
REM Flack x = 0.093 ( 0.009 ) from 385 Parsons' quotients
REM Formula found by SHELXT: C5 I N Cu Br
CELL 1.54184 4.0975 11.5751 16.3426 90 90 90
ZERR 4 0.0002 0.0006 0.0008 0 0 0
LATT -1
SYMM 0.5-X,-Y,0.5+Z
SYMM -X,0.5+Y,0.5-Z
SYMM 0.5+X,0.5-Y,-Z
SFAC C H Br Cu I N
UNIT 20 16 4 4 4 4

L.S. 4
PLAN  2
SIZE 0.06 0.101 0.518
TEMP -183.15
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2
acta
TWIN -1 0 0 0 -1 0 0 0 -1 2
REM <olex2.extras>
REM <HklSrc "%.\\exp_849.hkl">
REM </olex2.extras>

WGHT    0.050700
BASF   0.09716
FVAR       0.34346
I1    5    0.909531    0.628274    0.587405    11.00000    0.01044    0.00738 =
         0.00962    0.00293   -0.00032    0.00037
BR1   3    0.460698    0.193136    0.388065    11.00000    0.02786    0.00684 =
         0.02655   -0.00252    0.00144    0.00166
CU1   4    0.424040    0.672286    0.488996    11.00000    0.01415    0.00731 =
         0.01079   -0.00113   -0.00189    0.00087
N1    6    0.350986    0.545771    0.403233    11.00000    0.01477    0.00974 =
         0.01026    0.00177    0.00111    0.00310
C3    1    0.173887    0.372722    0.293080    11.00000    0.02749    0.01275 =
         0.00745   -0.00433    0.00044   -0.00798
AFIX  43
H3    2    0.116496    0.312989    0.255903    11.00000   -1.20000
AFIX   0
C5    1    0.186495    0.571511    0.334416    11.00000    0.02172    0.00976 =
         0.01541    0.00078   -0.00517    0.00174
AFIX  43
H5    2    0.131552    0.649972    0.324364    11.00000   -1.20000
AFIX   0
C2    1    0.339757    0.348460    0.364539    11.00000    0.01822    0.01126 =
         0.01103    0.00001    0.00292   -0.00272
C1    1    0.428257    0.435751    0.417909    11.00000    0.01558    0.01274 =
         0.00767    0.00096    0.00483   -0.00379
AFIX  43
H1    2    0.546674    0.416940    0.466077    11.00000   -1.20000
AFIX   0
C4    1    0.092349    0.488545    0.276942    11.00000    0.02383    0.01530 =
         0.01069   -0.00328   -0.00801   -0.00325
AFIX  43
H4    2   -0.022576    0.509616    0.228712    11.00000   -1.20000
AFIX   0
HKLF 4




REM  exp_849_a.res in P2(1)2(1)2(1)
REM wR2 = 0.0792, GooF = S = 1.065, Restrained GooF = 1.065 for all data
REM R1 = 0.0315 for 1308 Fo > 4sig(Fo) and 0.0319 for all 1329 data
REM 83 parameters refined using 0 restraints

END

WGHT      0.0507      0.0000

REM Highest difference peak  0.928,  deepest hole -1.173,  1-sigma level  0.239
Q1    1   0.6642  0.6479  0.5857  11.00000  0.05    0.93
Q2    1   1.2764  0.6191  0.6442  11.00000  0.05    0.85
;
_shelx_res_checksum              51754
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.478
_oxdiff_exptl_absorpt_empirical_full_min 0.624
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.903(11)
2 0.097(11)

####################################################################### 
# 
# 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_hy324
_database_code_depnum_ccdc_archive 'CCDC 2053633'
loop_
_audit_author_name
_audit_author_address
'Tomohito ide'
;National Institute of Technology, Tokyo College
Japan
;
_audit_update_record             
;
2021-03-13 deposited with the CCDC.	2021-06-08 downloaded from the CCDC.
;
_audit_creation_date             2021-03-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H9 Cl Cu N'
_chemical_formula_sum            'C7 H9 Cl Cu N'
_chemical_formula_weight         206.14
_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 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   13.4029(5)
_cell_length_b                   14.8238(6)
_cell_length_c                   7.9397(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.657(4)
_cell_angle_gamma                90
_cell_volume                     1550.27(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4137
_cell_measurement_temperature    90(2)
_cell_measurement_theta_max      76.1310
_cell_measurement_theta_min      6.7250
_shelx_estimated_absorpt_T_max   0.646
_shelx_estimated_absorpt_T_min   0.122
_exptl_absorpt_coefficient_mu    6.460
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.766
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.561
_exptl_crystal_size_mid          0.142
_exptl_crystal_size_min          0.074
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0216
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4657
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.283
_diffrn_reflns_theta_min         5.970
_diffrn_ambient_temperature      90
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -108.00 -56.00   0.50    0.05    --  -46.45-152.00 -49.00  104
  2  ω   -141.00 -77.00   0.50    0.05    -- -102.00-121.00 109.00  128
  3  ω    -23.00  24.00   0.50    0.05    --  -46.45  19.00-150.00   94
  4  ω    -59.00 -29.00   0.50    0.05    -- -102.00  61.00-120.00   60
  5  ω    -64.00 -38.00   0.50    0.05    -- -102.00  61.00-150.00   52
  6  ω    -76.00 -51.00   0.50    0.05    --  -46.45 121.00-167.00   50
  7  ω   -102.00 -31.00   0.50    0.05    -- -102.00  77.00-150.00  142
  8  ω    -69.00 -37.00   0.50    0.05    -- -102.00  61.00  30.00   64
  9  ω    -60.00 -29.00   0.50    0.05    -- -102.00  61.00  60.00   62
 10  ω     62.00 102.00   0.50    0.05    --   46.45 152.00  -7.00   80
 11  ω    101.00 143.00   0.50    0.05    --  104.61 121.00-167.00   84
 12  ω     93.00 175.00   0.50    0.05    --  104.61  30.00-180.00  164
 13  ω     91.00 126.00   0.50    0.05    --  104.61-152.00 -49.00   70
 14  ω     52.00  77.00   0.50    0.05    --   46.45-121.00 109.00   50
 15  ω     71.00  96.00   0.50    0.05    --  104.61-121.00 109.00   50
 16  ω     54.00  99.00   0.50    0.05    --  104.61 -94.00 120.00   90
 17  ω     50.00 105.00   0.50    0.05    --  104.61 -94.00  30.00  110
 18  ω    102.00 165.00   0.50    0.05    --  104.61  30.00 120.00  126
 19  ω     26.00 118.00   0.50    0.05    --   46.45  77.00   0.00  184
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0544909000
_diffrn_orient_matrix_UB_12      -0.0904311000
_diffrn_orient_matrix_UB_13      -0.0137739000
_diffrn_orient_matrix_UB_21      0.1024937000
_diffrn_orient_matrix_UB_22      0.0497753000
_diffrn_orient_matrix_UB_23      0.0201096000
_diffrn_orient_matrix_UB_31      0.0151067000
_diffrn_orient_matrix_UB_32      -0.0114124000
_diffrn_orient_matrix_UB_33      0.1958932000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1500
_reflns_number_total             1549
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.712
_refine_diff_density_rms         0.097
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     93
_refine_ls_number_reflns         1549
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0325
_refine_ls_restrained_S_all      1.119
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0519P)²+2.7299P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0889
_refine_ls_wR_factor_ref         0.0894
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C1(H1), C3(H3)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.55762(3) 0.43603(2) 0.61996(4) 0.02274(16) Uani 1 1 d . . . . .
Cl1 Cl 0.37895(4) 0.46188(4) 0.58076(6) 0.01621(16) Uani 1 1 d . . . . .
N1 N 0.59736(14) 0.31385(12) 0.5461(2) 0.0150(4) Uani 1 1 d . . . . .
C5 C 0.60808(15) 0.24196(15) 0.6516(3) 0.0144(4) Uani 1 1 d . . . . .
H5 H 0.597620 0.250231 0.765705 0.017 Uiso 1 1 calc R U . . .
C1 C 0.61135(16) 0.30142(15) 0.3845(3) 0.0152(4) Uani 1 1 d . . . . .
H1 H 0.603692 0.351811 0.309313 0.018 Uiso 1 1 calc R U . . .
C2 C 0.63643(16) 0.21867(15) 0.3219(3) 0.0152(4) Uani 1 1 d . . . . .
C4 C 0.63352(16) 0.15669(15) 0.6026(3) 0.0169(4) Uani 1 1 d . . . . .
C3 C 0.64857(17) 0.14601(15) 0.4347(3) 0.0168(4) Uani 1 1 d . . . . .
H3 H 0.667249 0.088673 0.396944 0.020 Uiso 1 1 calc R U . . .
C6 C 0.64917(19) 0.20915(16) 0.1386(3) 0.0203(5) Uani 1 1 d . . . . .
H6A H 0.587605 0.182576 0.070966 0.030 Uiso 1 1 calc R U . . .
H6B H 0.707353 0.169966 0.132991 0.030 Uiso 1 1 calc R U . . .
H6C H 0.660845 0.268708 0.092273 0.030 Uiso 1 1 calc R U . . .
C7 C 0.6463(2) 0.07861(16) 0.7253(3) 0.0240(5) Uani 1 1 d . . . . .
H7A H 0.718389 0.071325 0.775259 0.036 Uiso 1 1 calc R U . . .
H7B H 0.621066 0.023417 0.663895 0.036 Uiso 1 1 calc R U . . .
H7C H 0.607857 0.090141 0.816702 0.036 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
Cu1 0.0314(3) 0.0175(2) 0.0210(2) -0.00327(12) 0.00908(16) 0.00587(13)
Cl1 0.0172(3) 0.0170(3) 0.0145(3) 0.00245(18) 0.00319(19) -0.00026(17)
N1 0.0165(9) 0.0148(9) 0.0142(8) -0.0025(7) 0.0040(7) 0.0003(7)
C5 0.0143(10) 0.0168(11) 0.0123(9) -0.0005(8) 0.0026(7) 0.0013(8)
C1 0.0180(10) 0.0139(10) 0.0134(9) 0.0003(8) 0.0018(8) -0.0016(8)
C2 0.0132(9) 0.0186(11) 0.0136(10) -0.0027(8) 0.0016(8) -0.0002(8)
C4 0.0146(10) 0.0178(11) 0.0173(10) 0.0010(8) 0.0007(8) 0.0012(8)
C3 0.0182(10) 0.0145(10) 0.0170(10) -0.0032(8) 0.0015(8) 0.0010(8)
C6 0.0253(12) 0.0215(12) 0.0146(10) -0.0029(9) 0.0047(8) 0.0026(9)
C7 0.0326(13) 0.0185(11) 0.0212(12) 0.0050(9) 0.0058(10) 0.0041(9)

_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 Cu1 2.9195(7) 5_666 ?
Cu1 Cu1 2.7982(7) 2_656 ?
Cu1 Cl1 2.4018(6) 2_656 ?
Cu1 Cl1 2.3880(6) . ?
Cu1 Cl1 2.4604(6) 5_666 ?
Cu1 N1 2.0058(19) . ?
N1 C5 1.347(3) . ?
N1 C1 1.343(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.384(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.388(3) . ?
C2 C3 1.391(3) . ?
C2 C6 1.503(3) . ?
C4 C3 1.394(3) . ?
C4 C7 1.502(3) . ?
C3 H3 0.9500 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?

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
Cu1 Cu1 Cu1 100.60(2) 2_656 5_666 ?
Cl1 Cu1 Cu1 54.484(17) . 2_656 ?
Cl1 Cu1 Cu1 126.13(2) 2_656 5_666 ?
Cl1 Cu1 Cu1 51.848(16) 5_666 5_666 ?
Cl1 Cu1 Cu1 54.024(16) 2_656 2_656 ?
Cl1 Cu1 Cu1 141.443(15) 5_666 2_656 ?
Cl1 Cu1 Cu1 54.122(17) . 5_666 ?
Cl1 Cu1 Cl1 105.44(2) . 2_656 ?
Cl1 Cu1 Cl1 105.97(2) . 5_666 ?
Cl1 Cu1 Cl1 116.18(2) 2_656 5_666 ?
N1 Cu1 Cu1 122.20(5) . 5_666 ?
N1 Cu1 Cu1 115.37(5) . 2_656 ?
N1 Cu1 Cl1 111.64(6) . 2_656 ?
N1 Cu1 Cl1 102.93(6) . 5_666 ?
N1 Cu1 Cl1 114.89(6) . . ?
Cu1 Cl1 Cu1 129.60(3) 2_656 5_666 ?
Cu1 Cl1 Cu1 71.49(2) . 2_656 ?
Cu1 Cl1 Cu1 74.03(2) . 5_666 ?
C5 N1 Cu1 122.43(14) . . ?
C1 N1 Cu1 119.64(15) . . ?
C1 N1 C5 117.90(19) . . ?
N1 C5 H5 118.3 . . ?
N1 C5 C4 123.47(19) . . ?
C4 C5 H5 118.3 . . ?
N1 C1 H1 118.3 . . ?
N1 C1 C2 123.3(2) . . ?
C2 C1 H1 118.3 . . ?
C1 C2 C3 117.5(2) . . ?
C1 C2 C6 120.5(2) . . ?
C3 C2 C6 122.0(2) . . ?
C5 C4 C3 117.4(2) . . ?
C5 C4 C7 121.7(2) . . ?
C3 C4 C7 120.9(2) . . ?
C2 C3 C4 120.5(2) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

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 N1 C5 C4 178.72(16) . . . . ?
Cu1 N1 C1 C2 -178.37(16) . . . . ?
N1 C5 C4 C3 0.0(3) . . . . ?
N1 C5 C4 C7 179.0(2) . . . . ?
N1 C1 C2 C3 -0.8(3) . . . . ?
N1 C1 C2 C6 178.9(2) . . . . ?
C5 N1 C1 C2 -0.2(3) . . . . ?
C5 C4 C3 C2 -1.1(3) . . . . ?
C1 N1 C5 C4 0.6(3) . . . . ?
C1 C2 C3 C4 1.4(3) . . . . ?
C6 C2 C3 C4 -178.3(2) . . . . ?
C7 C4 C3 C2 179.9(2) . . . . ?

_shelx_res_file                  
;
TITL hy324_a.res in C2/c
    hy324.res
    created by SHELXL-2018/3 at 20:06:05 on 13-Mar-2021
REM Old TITL hy324_a.res in C2/c
REM SHELXT solution in C2/c: R1 0.215, Rweak 0.128, Alpha 0.029
REM <I/s> 1.222 for 62 systematic absences, Orientation as input
REM Formula found by SHELXT: C6 Cl2 N
CELL 1.54184 13.4029 14.8238 7.9397 90 100.657 90
ZERR 8 0.0005 0.0006 0.0003 0 0.004 0
LATT 7
SYMM -X,+Y,0.5-Z
SFAC C H Cl Cu N
UNIT 56 72 8 8 8

L.S. 10
PLAN  1
SIZE 0.074 0.142 0.561
TEMP -183.15
CONF
BOND
list 4
MORE -1
BOND $H
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\hy324.hkl">
REM </olex2.extras>

WGHT    0.051900    2.729900
FVAR       0.45296
CU1   4    0.557623    0.436029    0.619959    11.00000    0.03138    0.01748 =
         0.02100   -0.00327    0.00908    0.00587
CL1   3    0.378954    0.461876    0.580765    11.00000    0.01723    0.01699 =
         0.01451    0.00245    0.00319   -0.00026
N1    5    0.597362    0.313849    0.546100    11.00000    0.01647    0.01482 =
         0.01418   -0.00247    0.00397    0.00028
C5    1    0.608080    0.241963    0.651594    11.00000    0.01431    0.01679 =
         0.01225   -0.00053    0.00261    0.00130
AFIX  43
H5    2    0.597620    0.250231    0.765705    11.00000   -1.20000
AFIX   0
C1    1    0.611349    0.301425    0.384541    11.00000    0.01802    0.01389 =
         0.01341    0.00032    0.00183   -0.00157
AFIX  43
H1    2    0.603692    0.351811    0.309313    11.00000   -1.20000
AFIX   0
C2    1    0.636431    0.218674    0.321924    11.00000    0.01320    0.01859 =
         0.01360   -0.00269    0.00160   -0.00021
C4    1    0.633523    0.156690    0.602586    11.00000    0.01462    0.01778 =
         0.01733    0.00104    0.00068    0.00120
C3    1    0.648568    0.146009    0.434662    11.00000    0.01824    0.01447 =
         0.01698   -0.00318    0.00148    0.00104
AFIX  43
H3    2    0.667249    0.088673    0.396944    11.00000   -1.20000
AFIX   0
C6    1    0.649167    0.209152    0.138583    11.00000    0.02532    0.02149 =
         0.01456   -0.00290    0.00468    0.00256
AFIX 137
H6A   2    0.587605    0.182576    0.070966    11.00000   -1.50000
H6B   2    0.707353    0.169966    0.132991    11.00000   -1.50000
H6C   2    0.660845    0.268708    0.092273    11.00000   -1.50000
AFIX   0
C7    1    0.646321    0.078609    0.725271    11.00000    0.03263    0.01849 =
         0.02121    0.00499    0.00582    0.00406
AFIX 137
H7A   2    0.718389    0.071325    0.775259    11.00000   -1.50000
H7B   2    0.621066    0.023417    0.663895    11.00000   -1.50000
H7C   2    0.607857    0.090141    0.816702    11.00000   -1.50000
AFIX   0
HKLF 4




REM  hy324_a.res in C2/c
REM wR2 = 0.0894, GooF = S = 1.119, Restrained GooF = 1.119 for all data
REM R1 = 0.0325 for 1500 Fo > 4sig(Fo) and 0.0331 for all 1549 data
REM 93 parameters refined using 0 restraints

END

WGHT      0.0519      2.7298

REM Highest difference peak  0.392,  deepest hole -0.712,  1-sigma level  0.097
Q1    1   0.5572  0.5607  0.6216  11.00000  0.05    0.39
;
_shelx_res_checksum              53250
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.642
_oxdiff_exptl_absorpt_empirical_full_min 0.569
####################################################################### 
# 
# 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_hy312
_database_code_depnum_ccdc_archive 'CCDC 2053631'
loop_
_audit_author_name
_audit_author_address
'Tomohito ide'
;National Institute of Technology, Tokyo College
Japan
;
_audit_update_record             
;
2021-03-13 deposited with the CCDC.	2021-06-08 downloaded from the CCDC.
;
_audit_creation_date             2021-03-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H4 Br2 Cu N'
_chemical_formula_sum            'C5 H4 Br2 Cu N'
_chemical_formula_weight         301.45
_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 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.7546(3)
_cell_length_b                   3.91060(10)
_cell_length_c                   21.0487(7)
_cell_angle_alpha                90
_cell_angle_beta                 100.957(4)
_cell_angle_gamma                90
_cell_volume                     707.48(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2954
_cell_measurement_temperature    90
_cell_measurement_theta_max      75.7910
_cell_measurement_theta_min      4.3150
_shelx_estimated_absorpt_T_max   0.546
_shelx_estimated_absorpt_T_min   0.034
_exptl_absorpt_coefficient_mu    16.789
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46129
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.830
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.616
_exptl_crystal_size_mid          0.081
_exptl_crystal_size_min          0.041
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            3394
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.917
_diffrn_reflns_theta_min         4.279
_diffrn_ambient_temperature      90
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -98.00 -54.00   0.50    0.05    --  -46.45 -36.00  62.00   88
  2  ω    -69.00 -44.00   0.50    0.05    -- -102.00  61.00   0.00   50
  3  ω    -63.00 -36.00   0.50    0.05    -- -102.00  61.00 -30.00   54
  4  ω    -68.00 -31.00   0.50    0.05    -- -102.00  61.00 -60.00   74
  5  ω    -30.00  -5.00   0.50    0.05    --  -46.45  36.00-141.00   50
  6  ω    -67.00 -36.00   0.50    0.05    -- -102.00  61.00-180.00   62
  7  ω    -67.00 -31.00   0.50    0.05    -- -102.00  61.00-150.00   72
  8  ω    -99.00 -29.00   0.50    0.05    -- -102.00  77.00-150.00  140
  9  ω    -69.00 -30.00   0.50    0.05    -- -102.00  61.00  60.00   78
 10  ω    -68.00 -43.00   0.50    0.05    -- -102.00  61.00 150.00   50
 11  ω   -156.00-131.00   0.50    0.05    -- -102.00 -36.00  62.00   50
 12  ω    -26.00  36.00   0.50    0.05    --   46.45 -36.00  62.00  124
 13  ω     94.00 119.00   0.50    0.05    --  104.61  15.00 -60.00   50
 14  ω    136.00 161.00   0.50    0.05    --  104.61  15.00 -60.00   50
 15  ω     96.00 171.00   0.50    0.05    --  104.61  36.00-141.00  150
 16  ω     62.00 104.00   0.50    0.05    --  104.61 -94.00-150.00   84
 17  ω     36.00 119.00   0.50    0.05    --   46.45  36.00-141.00  166
 18  ω     43.00  73.00   0.50    0.05    --  104.61 -61.00  60.00   60
 19  ω    -26.00  26.00   0.50    0.05    --   46.45 -19.00 -90.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0344990000
_diffrn_orient_matrix_UB_12      0.1406265000
_diffrn_orient_matrix_UB_13      -0.0641738000
_diffrn_orient_matrix_UB_21      -0.1622583000
_diffrn_orient_matrix_UB_22      -0.1162155000
_diffrn_orient_matrix_UB_23      -0.0351913000
_diffrn_orient_matrix_UB_31      -0.0677471000
_diffrn_orient_matrix_UB_32      0.3491970000
_diffrn_orient_matrix_UB_33      0.0142214000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1353
_reflns_number_total             1406
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.760
_refine_diff_density_min         -1.298
_refine_diff_density_rms         0.227
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.152
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1406
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0352
_refine_ls_restrained_S_all      1.152
_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)+(0.0483P)²+3.8749P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0933
_refine_ls_wR_factor_ref         0.0941
_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:
 C1(H1), C3(H3), C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
Br1 Br 0.16867(5) 1.11684(12) 0.32338(2) 0.01311(17) Uani 1 1 d . . . . .
Br2 Br 0.75118(6) 0.16087(14) 0.51887(2) 0.01748(17) Uani 1 1 d . . . . .
Cu1 Cu 0.31826(8) 0.6275(2) 0.29599(4) 0.0178(2) Uani 1 1 d . . . . .
N1 N 0.5395(4) 0.5528(12) 0.34313(19) 0.0152(8) Uani 1 1 d . . . . .
C1 C 0.5688(6) 0.4072(13) 0.4019(2) 0.0155(10) Uani 1 1 d . . . . .
H1 H 0.484167 0.340795 0.421427 0.019 Uiso 1 1 calc R U . . .
C3 C 0.8447(5) 0.4408(14) 0.4067(2) 0.0167(10) Uani 1 1 d . . . . .
H3 H 0.948451 0.399301 0.428447 0.020 Uiso 1 1 calc R U . . .
C2 C 0.7187(6) 0.3515(12) 0.4346(2) 0.0148(10) Uani 1 1 d . . . . .
C4 C 0.8140(6) 0.5922(14) 0.3462(2) 0.0188(10) Uani 1 1 d . . . . .
H4 H 0.896952 0.659492 0.325718 0.023 Uiso 1 1 calc R U . . .
C5 C 0.6610(6) 0.6445(13) 0.3159(2) 0.0154(10) Uani 1 1 d . . . . .
H5 H 0.640904 0.748862 0.274386 0.018 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
Br1 0.0121(3) 0.0163(3) 0.0113(3) 0.00050(17) 0.00325(18) -0.00016(17)
Br2 0.0185(3) 0.0207(3) 0.0120(3) 0.00160(19) -0.00022(19) 0.00017(19)
Cu1 0.0121(4) 0.0239(4) 0.0171(4) 0.0026(3) 0.0020(3) 0.0017(3)
N1 0.0086(18) 0.022(2) 0.0144(19) -0.0017(17) 0.0009(15) -0.0001(16)
C1 0.013(2) 0.023(3) 0.012(2) 0.0008(19) 0.0058(17) -0.0010(19)
C3 0.009(2) 0.022(3) 0.018(2) -0.001(2) 0.0008(17) 0.0014(19)
C2 0.019(2) 0.012(2) 0.012(2) 0.0028(18) 0.0006(18) -0.0013(18)
C4 0.011(2) 0.029(3) 0.017(2) -0.002(2) 0.0055(18) -0.003(2)
C5 0.013(2) 0.022(3) 0.011(2) -0.0019(18) 0.0033(18) -0.0013(18)

_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 Cu1 2.4487(9) . ?
Br1 Cu1 2.5370(9) 2 ?
Br1 Cu1 2.5146(9) 1_565 ?
Br2 C2 1.895(5) . ?
Cu1 Cu1 2.8495(11) 2_545 ?
Cu1 Cu1 2.8495(11) 2 ?
Cu1 N1 2.023(4) . ?
N1 C1 1.341(6) . ?
N1 C5 1.349(6) . ?
C1 H1 0.9500 . ?
C1 C2 1.379(7) . ?
C3 H3 0.9500 . ?
C3 C2 1.389(7) . ?
C3 C4 1.383(7) . ?
C4 H4 0.9500 . ?
C4 C5 1.385(7) . ?
C5 H5 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
Cu1 Br1 Cu1 103.97(3) . 1_565 ?
Cu1 Br1 Cu1 69.69(3) . 2 ?
Cu1 Br1 Cu1 68.67(2) 1_565 2 ?
Br1 Cu1 Br1 103.97(3) . 1_545 ?
Br1 Cu1 Br1 111.89(3) . 2_545 ?
Br1 Cu1 Br1 109.72(3) 1_545 2_545 ?
Br1 Cu1 Cu1 56.614(19) . 2 ?
Br1 Cu1 Cu1 53.70(3) 2_545 2_545 ?
Br1 Cu1 Cu1 56.034(18) 1_545 2_545 ?
Br1 Cu1 Cu1 122.09(4) 1_545 2 ?
Br1 Cu1 Cu1 121.47(4) . 2_545 ?
Br1 Cu1 Cu1 55.29(3) 2_545 2 ?
Cu1 Cu1 Cu1 86.66(4) 2 2_545 ?
N1 Cu1 Br1 105.35(13) . 1_545 ?
N1 Cu1 Br1 120.17(13) . . ?
N1 Cu1 Br1 105.32(12) . 2_545 ?
N1 Cu1 Cu1 118.23(13) . 2_545 ?
N1 Cu1 Cu1 132.17(13) . 2 ?
C1 N1 Cu1 120.8(3) . . ?
C1 N1 C5 118.5(4) . . ?
C5 N1 Cu1 120.8(3) . . ?
N1 C1 H1 119.2 . . ?
N1 C1 C2 121.7(4) . . ?
C2 C1 H1 119.2 . . ?
C2 C3 H3 121.1 . . ?
C4 C3 H3 121.1 . . ?
C4 C3 C2 117.7(4) . . ?
C1 C2 Br2 119.3(4) . . ?
C1 C2 C3 120.4(4) . . ?
C3 C2 Br2 120.3(4) . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.3(4) . . ?
C5 C4 H4 120.3 . . ?
N1 C5 C4 122.4(5) . . ?
N1 C5 H5 118.8 . . ?
C4 C5 H5 118.8 . . ?

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 N1 C1 C2 179.5(4) . . . . ?
Cu1 N1 C5 C4 -178.9(4) . . . . ?
N1 C1 C2 Br2 177.5(4) . . . . ?
N1 C1 C2 C3 -1.1(8) . . . . ?
C1 N1 C5 C4 0.3(8) . . . . ?
C3 C4 C5 N1 -0.1(8) . . . . ?
C2 C3 C4 C5 -0.7(8) . . . . ?
C4 C3 C2 Br2 -177.3(4) . . . . ?
C4 C3 C2 C1 1.3(8) . . . . ?
C5 N1 C1 C2 0.2(8) . . . . ?

_shelx_res_file                  
;
TITL hy312_a.res in P2(1)/n
    hy312.res
    created by SHELXL-2018/3 at 20:20:16 on 13-Mar-2021
REM Old TITL hy312_a.res in P2(1)
REM SHELXT solution in P2(1)/n: R1 0.059, Rweak 0.002, Alpha 0.021
REM <I/s> 1.822 for 217 systematic absences, Orientation as input
REM Formula found by SHELXT: C5 N Br2 Cu
CELL 1.54184 8.7546 3.9106 21.0487 90 100.957 90
ZERR 4 0.0003 0.0001 0.0007 0 0.004 0
LATT 1
SYMM 0.5-X,0.5+Y,0.5-Z
SFAC C H Br Cu N
UNIT 20 16 8 4 4

L.S. 10
PLAN  1
SIZE 0.041 0.081 0.616
TEMP -183.15
CONF
BOND
LIST 6
MORE -1
BOND $H
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\hy312.hkl">
REM </olex2.extras>

WGHT    0.048300    3.874900
FVAR       0.43939
BR1   3    0.168668    1.116843    0.323379    11.00000    0.01213    0.01631 =
         0.01128    0.00050    0.00325   -0.00016
BR2   3    0.751177    0.160869    0.518867    11.00000    0.01851    0.02073 =
         0.01198    0.00160   -0.00022    0.00017
CU1   4    0.318264    0.627547    0.295985    11.00000    0.01207    0.02387 =
         0.01707    0.00255    0.00200    0.00174
N1    5    0.539530    0.552800    0.343134    11.00000    0.00864    0.02197 =
         0.01439   -0.00172    0.00093   -0.00015
C1    1    0.568838    0.407229    0.401866    11.00000    0.01286    0.02321 =
         0.01188    0.00078    0.00575   -0.00105
AFIX  43
H1    2    0.484167    0.340795    0.421427    11.00000   -1.20000
AFIX   0
C3    1    0.844707    0.440781    0.406716    11.00000    0.00907    0.02226 =
         0.01799   -0.00061    0.00084    0.00141
AFIX  43
H3    2    0.948451    0.399301    0.428447    11.00000   -1.20000
AFIX   0
C2    1    0.718744    0.351521    0.434586    11.00000    0.01916    0.01219 =
         0.01203    0.00281    0.00061   -0.00133
C4    1    0.813991    0.592160    0.346232    11.00000    0.01106    0.02888 =
         0.01749   -0.00170    0.00549   -0.00304
AFIX  43
H4    2    0.896952    0.659492    0.325718    11.00000   -1.20000
AFIX   0
C5    1    0.661030    0.644522    0.315898    11.00000    0.01333    0.02170 =
         0.01140   -0.00193    0.00326   -0.00132
AFIX  43
H5    2    0.640904    0.748862    0.274386    11.00000   -1.20000
AFIX   0
HKLF 4




REM  hy312_a.res in P2(1)/n
REM wR2 = 0.0941, GooF = S = 1.152, Restrained GooF = 1.152 for all data
REM R1 = 0.0352 for 1353 Fo > 4sig(Fo) and 0.0363 for all 1406 data
REM 82 parameters refined using 0 restraints

END

WGHT      0.0483      3.8749

REM Highest difference peak  0.760,  deepest hole -1.298,  1-sigma level  0.227
Q1    1   0.7406 -0.2287  0.5172  11.00000  0.05    0.76
;
_shelx_res_checksum              23448
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.153
_oxdiff_exptl_absorpt_empirical_full_min 0.633
####################################################################### 
# 
# 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_hy327
_database_code_depnum_ccdc_archive 'CCDC 2053634'
loop_
_audit_author_name
_audit_author_address
'Tomohito ide'
;National Institute of Technology, Tokyo College
Japan
;
_audit_update_record             
;
2021-03-13 deposited with the CCDC.	2021-06-08 downloaded from the CCDC.
;
_audit_creation_date             2021-03-13
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '3(C21 H27 Cl1 Cu1 N3)'
_chemical_formula_sum            'C63 H81 Cl3 Cu3 N9'
_chemical_formula_weight         1261.33
_chemical_absolute_configuration ?
_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 0.0181 0.0091 '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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 '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      trigonal
_space_group_IT_number           160
_space_group_name_H-M_alt        'R 3 m'
_space_group_name_Hall           'R 3 -2"'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-y, -x, z'
'-x+y, y, z'
'x, x-y, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'-y+2/3, -x+1/3, z+1/3'
'-x+y+2/3, y+1/3, z+1/3'
'x+2/3, x-y+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-y+1/3, -x+2/3, z+2/3'
'-x+y+1/3, y+2/3, z+2/3'
'x+1/3, x-y+2/3, z+2/3'

_cell_length_a                   14.7196(5)
_cell_length_b                   14.7196(5)
_cell_length_c                   8.3670(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1569.97(13)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    1527
_cell_measurement_temperature    90
_cell_measurement_theta_max      76.2530
_cell_measurement_theta_min      8.7270
_shelx_estimated_absorpt_T_max   0.484
_shelx_estimated_absorpt_T_min   0.355
_exptl_absorpt_coefficient_mu    2.701
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.75470
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.334
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             660
_exptl_crystal_size_max          0.484
_exptl_crystal_size_mid          0.403
_exptl_crystal_size_min          0.314
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0119
_diffrn_reflns_av_unetI/netI     0.0115
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            1562
_diffrn_reflns_point_group_measured_fraction_full 0.860
_diffrn_reflns_point_group_measured_fraction_max 0.817
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.408
_diffrn_reflns_theta_min         8.746
_diffrn_ambient_temperature      90
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -14.00  55.00   0.50    0.05    --   46.45-100.00  21.00  138
  2  ω     34.00  70.00   0.50    0.05    --  104.61 -61.00 -30.00   72
  3  ω     35.00  61.00   0.50    0.05    --  104.61 -61.00 -60.00   52
  4  ω     92.00 117.00   0.50    0.05    --  104.61  24.00 -22.00   50
  5  ω    140.00 178.00   0.50    0.05    --  104.61  24.00 -22.00   76
  6  ω     -3.00  29.00   0.50    0.05    --  -46.45  19.00 120.00   64
  7  ω    -64.00 -33.00   0.50    0.05    -- -102.00  61.00 120.00   62
  8  ω    -69.00 -44.00   0.50    0.05    -- -102.00  61.00  60.00   50
  9  ω    -68.00 -42.00   0.50    0.05    -- -102.00  61.00 -60.00   52
 10  ω    -63.00 -38.00   0.50    0.05    -- -102.00  58.00-105.00   50
 11  ω   -169.00 -90.00   0.50    0.05    -- -102.00 -34.00 127.00  158
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1053457000
_diffrn_orient_matrix_UB_12      0.0094583000
_diffrn_orient_matrix_UB_13      -0.0486249000
_diffrn_orient_matrix_UB_21      -0.0104233000
_diffrn_orient_matrix_UB_22      0.0364408000
_diffrn_orient_matrix_UB_23      -0.1681094000
_diffrn_orient_matrix_UB_31      0.0583871000
_diffrn_orient_matrix_UB_32      0.1148640000
_diffrn_orient_matrix_UB_33      0.0573544000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_reflns_Friedel_coverage         0.693
_reflns_Friedel_fraction_full    0.734
_reflns_Friedel_fraction_max     0.676
_reflns_number_gt                679
_reflns_number_total             679
_reflns_odcompleteness_completeness 98.60
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.038
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.11(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     58
_refine_ls_number_reflns         679
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0170
_refine_ls_R_factor_gt           0.0170
_refine_ls_restrained_S_all      1.124
_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)+(0.0221P)²+1.5759P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0456
_refine_ls_wR_factor_ref         0.0456
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.89(3)
 0.11(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Others
 Fixed Sof: H6A(0.5) H6B(0.5) H6C(0.5) H7A(0.5) H7B(0.5) H7C(0.5)
4.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C1(H1), C3(H3)
4.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
N1 N 0.25632(9) 0.51264(18) 0.4823(3) 0.0136(5) Uani 1 2 d S T P . .
C5 C 0.23963(13) 0.4793(3) 0.6341(4) 0.0170(6) Uani 1 2 d S T P . .
H5 H 0.264637 0.529273 0.715050 0.020 Uiso 1 2 calc R U P . .
C4 C 0.18680(14) 0.3736(3) 0.6775(5) 0.0194(7) Uani 1 2 d S T P . .
C2 C 0.16617(13) 0.3323(3) 0.3960(4) 0.0168(7) Uani 1 2 d S T P . .
C1 C 0.21988(11) 0.4398(2) 0.3663(3) 0.0155(6) Uani 1 2 d S T P . .
H1 H 0.231141 0.462282 0.260564 0.019 Uiso 1 2 calc R U P . .
C3 C 0.15002(14) 0.3000(3) 0.5537(4) 0.0193(7) Uani 1 2 d S T P . .
H3 H 0.114395 0.228790 0.577532 0.023 Uiso 1 2 calc R U P . .
C6 C 0.12825(13) 0.2565(3) 0.2569(4) 0.0292(8) Uani 1 2 d S T P . .
H6A H 0.102478 0.186456 0.295772 0.044 Uiso 0.5 1 calc R U P A -1
H6B H 0.185308 0.274576 0.184288 0.044 Uiso 0.5 1 calc R U P A -1
H6C H 0.072901 0.260343 0.202294 0.044 Uiso 0.5 1 calc R U P A -1
C7 C 0.17086(15) 0.3417(3) 0.8500(4) 0.0330(10) Uani 1 2 d S T P . .
H7A H 0.101221 0.323778 0.882039 0.049 Uiso 0.5 1 calc R U P B -1
H7B H 0.221096 0.398872 0.914263 0.049 Uiso 0.5 1 calc R U P B -1
H7C H 0.180048 0.282080 0.864146 0.049 Uiso 0.5 1 calc R U P B -1
Cu1 Cu 0.333333 0.666667 0.42238(7) 0.0121(2) Uani 1 6 d S T P . .
Cl1 Cl 0.333333 0.666667 0.13335(13) 0.0136(3) Uani 1 6 d S T P . .

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
N1 0.0138(8) 0.0127(11) 0.0139(11) 0.0023(9) 0.0011(5) 0.0063(6)
C5 0.0201(10) 0.0148(15) 0.0144(14) -0.0003(12) -0.0002(6) 0.0074(7)
C4 0.0232(12) 0.0161(17) 0.0166(17) 0.0022(14) 0.0011(7) 0.0081(8)
C2 0.0203(11) 0.0136(13) 0.0143(18) 0.0005(14) 0.0003(7) 0.0068(7)
C1 0.0179(10) 0.0139(14) 0.0135(14) 0.0022(11) 0.0011(6) 0.0070(7)
C3 0.0208(12) 0.0120(16) 0.0222(19) 0.0047(13) 0.0023(7) 0.0060(8)
C6 0.0432(17) 0.0118(16) 0.0223(19) 0.0006(14) 0.0003(7) 0.0059(8)
C7 0.052(2) 0.0235(18) 0.014(2) 0.0052(15) 0.0026(7) 0.0118(9)
Cu1 0.0116(2) 0.0116(2) 0.0130(4) 0.000 0.000 0.00580(12)
Cl1 0.0144(4) 0.0144(4) 0.0119(6) 0.000 0.000 0.00721(18)

_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
N1 C5 1.340(4) . ?
N1 C1 1.343(4) . ?
N1 Cu1 2.026(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.395(5) . ?
C4 C3 1.398(5) . ?
C4 C7 1.500(5) . ?
C2 C1 1.392(4) . ?
C2 C3 1.382(5) . ?
C2 C6 1.513(4) . ?
C1 H1 0.9300 . ?
C3 H3 0.9300 . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
Cu1 Cl1 2.4183(12) . ?

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 117.7(3) . . ?
C5 N1 Cu1 122.8(2) . . ?
C1 N1 Cu1 119.43(19) . . ?
N1 C5 H5 118.2 . . ?
N1 C5 C4 123.6(3) . . ?
C4 C5 H5 118.2 . . ?
C5 C4 C3 117.1(3) . . ?
C5 C4 C7 120.8(3) . . ?
C3 C4 C7 122.1(3) . . ?
C1 C2 C6 119.4(3) . . ?
C3 C2 C1 117.6(3) . . ?
C3 C2 C6 123.0(3) . . ?
N1 C1 C2 123.4(3) . . ?
N1 C1 H1 118.3 . . ?
C2 C1 H1 118.3 . . ?
C4 C3 H3 119.7 . . ?
C2 C3 C4 120.5(3) . . ?
C2 C3 H3 119.7 . . ?
C2 C6 H6A 109.5 . . ?
C2 C6 H6B 109.5 . . ?
C2 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 Cu1 N1 114.10(6) 2_665 . ?
N1 Cu1 N1 114.10(6) 3_565 . ?
N1 Cu1 N1 114.09(6) 3_565 2_665 ?
N1 Cu1 Cl1 104.32(7) 3_565 . ?
N1 Cu1 Cl1 104.32(7) . . ?
N1 Cu1 Cl1 104.32(7) 2_665 . ?

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
N1 C5 C4 C3 0.000(2) . . . . ?
N1 C5 C4 C7 180.000(1) . . . . ?
C5 N1 C1 C2 0.000(1) . . . . ?
C5 C4 C3 C2 0.000(1) . . . . ?
C1 N1 C5 C4 0.000(2) . . . . ?
C1 C2 C3 C4 0.000(1) . . . . ?
C3 C2 C1 N1 0.000(1) . . . . ?
C6 C2 C1 N1 180.000(1) . . . . ?
C6 C2 C3 C4 180.000(1) . . . . ?
C7 C4 C3 C2 180.000(2) . . . . ?
Cu1 N1 C5 C4 180.000(1) . . . . ?
Cu1 N1 C1 C2 180.000(1) . . . . ?

_shelx_res_file                  
;
TITL hy327_a.res in R3m
    hy327.res
    created by SHELXL-2018/3 at 20:14:04 on 13-Mar-2021
REM Old TITL hy327_c.res in R32
REM SHELXT solution in R3m: R1 0.047, Rweak 0.065, Alpha 0.065
REM <I/s> 0.000 for 0 systematic absences, Orientation as input
REM Flack x = 0.118 ( 0.014 ) from 278 Parsons' quotients
REM Formula found by SHELXT: C18 Cl Cu N6
CELL 1.54184 14.7196 14.7196 8.367 90 90 120
ZERR 1 0.0005 0.0005 0.0004 0 0 0
LATT -3
SYMM -Y,+X-Y,+Z
SYMM +Y-X,-X,+Z
SYMM -Y,-X,+Z
SYMM +Y-X,+Y,+Z
SYMM +X,+X-Y,+Z
SFAC C H Cl Cu N
UNIT 63 81 3 3 9

L.S. 10
PLAN  9
SIZE 0.314 0.403 0.484
CONF
BOND
LIST 6
MORE -1
BOND $H
fmap 2
acta
TWIN -1 0 0 0 -1 0 0 0 -1 2
REM <olex2.extras>
REM <HklSrc "%.\\hy327.hkl">
REM </olex2.extras>

WGHT    0.022100    1.575900
BASF   0.11449
FVAR       0.56823
N1    5    0.256320    0.512641    0.482275    10.50000    0.01384    0.01266 =
         0.01394    0.00226    0.00113    0.00633
C5    1    0.239629    0.479257    0.634132    10.50000    0.02011    0.01480 =
         0.01439   -0.00033   -0.00017    0.00740
AFIX  43
H5    2    0.264637    0.529273    0.715050    10.50000   -1.20000
AFIX   0
C4    1    0.186803    0.373606    0.677498    10.50000    0.02321    0.01611 =
         0.01655    0.00218    0.00109    0.00805
C2    1    0.166171    0.332341    0.396033    10.50000    0.02033    0.01363 =
         0.01433    0.00054    0.00027    0.00681
C1    1    0.219884    0.439767    0.366290    10.50000    0.01790    0.01391 =
         0.01348    0.00218    0.00109    0.00695
AFIX  43
H1    2    0.231141    0.462282    0.260564    10.50000   -1.20000
AFIX   0
C3    1    0.150021    0.300043    0.553657    10.50000    0.02077    0.01195 =
         0.02221    0.00468    0.00234    0.00598
AFIX  43
H3    2    0.114395    0.228790    0.577532    10.50000   -1.20000
AFIX   0
C6    1    0.128248    0.256495    0.256875    10.50000    0.04318    0.01178 =
         0.02229    0.00060    0.00030    0.00589
PART -1
AFIX 137
H6A   2    0.102478    0.186456    0.295772    10.50000   -1.50000
H6B   2    0.185308    0.274576    0.184288    10.50000   -1.50000
H6C   2    0.072901    0.260343    0.202294    10.50000   -1.50000
AFIX   0
PART 0
C7    1    0.170858    0.341716    0.850003    10.50000    0.05228    0.02354 =
         0.01359    0.00519    0.00260    0.01177
PART -1
AFIX 137
H7A   2    0.101221    0.323778    0.882039    10.50000   -1.50000
H7B   2    0.221096    0.398872    0.914263    10.50000   -1.50000
H7C   2    0.180048    0.282080    0.864146    10.50000   -1.50000
AFIX   0
PART 0
CU1   4    0.333333    0.666667    0.422381    10.16667    0.01160    0.01160 =
         0.01296    0.00000    0.00000    0.00580
CL1   3    0.333333    0.666667    0.133347    10.16667    0.01442    0.01442 =
         0.01190    0.00000    0.00000    0.00721
HKLF 4




REM  hy327_a.res in R3m
REM wR2 = 0.0456, GooF = S = 1.124, Restrained GooF = 1.124 for all data
REM R1 = 0.0170 for 679 Fo > 4sig(Fo) and 0.0170 for all 679 data
REM 58 parameters refined using 1 restraints

END

WGHT      0.0221      1.5759

REM Highest difference peak  0.241,  deepest hole -0.244,  1-sigma level  0.038
Q1    1   0.3333  0.6667  0.5969  10.16667  0.05    0.24
Q2    1   0.3333  0.6667  0.2729  10.16667  0.05    0.23
Q3    1   0.3848  0.6152  0.1400  10.50000  0.05    0.15
Q4    1   0.3890  0.6657  0.2736  11.00000  0.05    0.15
Q5    1   0.1362  0.2723  0.1241  10.50000  0.05    0.13
Q6    1   0.3333  0.6667 -0.0521  10.16667  0.05    0.13
Q7    1   0.2844  0.5688  0.1091  10.50000  0.05    0.13
Q8    1   0.0835  0.1670  0.7427  10.50000  0.05    0.12
Q9    1   0.2399  0.6200  0.3761  10.50000  0.05    0.12
;
_shelx_res_checksum              49754
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.201
_oxdiff_exptl_absorpt_empirical_full_min 0.873
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.89(3)
2 0.11(3)

