# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_liy026
_database_code_depnum_ccdc_archive 'CCDC 2084388'
loop_
_audit_author_name
_audit_author_address
'Yuqiao Zhou'
;College of Chemistry, Sichuan University, Chengdu, China
China
;
_audit_update_record             
;
2021-05-18 deposited with the CCDC.	2022-01-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C12 H14 Cl2 Cu N2 O), C H Cl3'
_chemical_formula_sum            'C25 H29 Cl7 Cu2 N4 O2'
_chemical_formula_weight         792.75

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   11.4615(5)
_cell_length_b                   9.9184(4)
_cell_length_c                   14.1599(7)
_cell_angle_alpha                90
_cell_angle_beta                 104.423(2)
_cell_angle_gamma                90
_cell_volume                     1558.96(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9746
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      28.13

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_F_000             800
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.336
_exptl_crystal_size_mid          0.087
_exptl_crystal_size_min          0.062
_exptl_absorpt_coefficient_mu    1.996
_shelx_estimated_absorpt_T_min   0.554
_shelx_estimated_absorpt_T_max   0.886
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.7311
_exptl_absorpt_correction_T_max  0.9573
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22832
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.534
_diffrn_reflns_theta_max         28.342
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             7585
_reflns_number_gt                6103
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.855
_reflns_Friedel_fraction_max     0.954
_reflns_Friedel_fraction_full    0.970

_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. 
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0244P)²+0.9223P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Flack x determined using 2249 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.001(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         7585
_refine_ls_number_parameters     389
_refine_ls_number_restraints     28
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0847
_refine_ls_wR_factor_gt          0.0668
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_restrained_S_all      1.125
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.73495(6) 0.52035(6) 0.37065(5) 0.02884(17) Uani 1 1 d . . . . .
Cu2 Cu 0.78363(6) 0.41605(6) 0.14393(5) 0.03359(19) Uani 1 1 d . . . . .
Cl1 Cl 0.60038(12) 0.45629(14) 0.23107(10) 0.0344(3) Uani 1 1 d . . . . .
Cl2 Cl 0.72226(13) 0.74022(14) 0.33247(10) 0.0368(3) Uani 1 1 d . . . . .
Cl3 Cl 0.92472(12) 0.45291(14) 0.28685(10) 0.0336(3) Uani 1 1 d . . . . .
Cl4 Cl 0.78788(15) 0.19137(16) 0.15385(12) 0.0490(4) Uani 1 1 d . . . . .
O1 O 0.9336(4) 0.4733(4) 0.6469(3) 0.0448(11) Uani 1 1 d . . . . .
O2 O 0.7033(4) 0.7635(5) -0.0064(3) 0.0587(13) Uani 1 1 d . . . . .
N1 N 0.7644(4) 0.3272(4) 0.4251(3) 0.0295(10) Uani 1 1 d . . . . .
N2 N 0.8223(4) 0.5600(4) 0.5085(3) 0.0322(11) Uani 1 1 d . . . . .
N3 N 0.6569(4) 0.4103(5) 0.0098(3) 0.0342(11) Uani 1 1 d . . . . .
N4 N 0.7938(4) 0.6058(5) 0.1000(4) 0.0349(11) Uani 1 1 d . . . . .
C1 C 0.7319(6) 0.2116(6) 0.3790(4) 0.0408(15) Uani 1 1 d . . . . .
H1 H 0.676499 0.212923 0.316710 0.049 Uiso 1 1 calc R U . . .
C2 C 0.7766(6) 0.0886(6) 0.4194(5) 0.0453(16) Uani 1 1 d . . . . .
H2 H 0.750154 0.007114 0.385559 0.054 Uiso 1 1 calc R U . . .
C3 C 0.8592(6) 0.0852(6) 0.5084(4) 0.0416(15) Uani 1 1 d . . . . .
H3 H 0.892739 0.002082 0.535616 0.050 Uiso 1 1 calc R U . . .
C4 C 0.8926(5) 0.2054(5) 0.5574(4) 0.0362(14) Uani 1 1 d . . . . .
H4 H 0.948237 0.206743 0.619611 0.043 Uiso 1 1 calc R U . . .
C5 C 0.8429(5) 0.3223(5) 0.5137(4) 0.0286(12) Uani 1 1 d . . . . .
C6 C 0.8667(5) 0.4565(6) 0.5567(4) 0.0301(12) Uani 1 1 d . . . . .
C11 C 0.8552(5) 0.6817(5) 0.5707(4) 0.0315(12) Uani 1 1 d . . . . .
H11 H 0.903488 0.744452 0.540138 0.038 Uiso 1 1 calc R U . . .
C12 C 0.9370(6) 0.6205(6) 0.6654(4) 0.0382(14) Uani 1 1 d . . . . .
H12 H 1.021328 0.653702 0.673289 0.046 Uiso 1 1 calc R U . . .
C13 C 0.8976(6) 0.6520(8) 0.7556(5) 0.0558(19) Uani 1 1 d . . . . .
H13A H 0.945535 0.597069 0.809970 0.067 Uiso 1 1 calc R U . . .
H13B H 0.914699 0.748043 0.772428 0.067 Uiso 1 1 calc R U . . .
C14 C 0.7686(7) 0.6261(10) 0.7465(6) 0.074(3) Uani 1 1 d D . . . .
H14A H 0.744850 0.670557 0.801476 0.089 Uiso 1 1 calc R U . . .
H14B H 0.756732 0.527865 0.752381 0.089 Uiso 1 1 calc R U . . .
C15 C 0.6848(6) 0.6753(9) 0.6508(5) 0.061(2) Uani 1 1 d D . . . .
H15A H 0.645378 0.596239 0.613416 0.073 Uiso 1 1 calc R U . . .
H15B H 0.620877 0.732105 0.666123 0.073 Uiso 1 1 calc R U . . .
C16 C 0.7481(6) 0.7546(6) 0.5884(4) 0.0427(14) Uani 1 1 d D . . . .
H16A H 0.690800 0.773874 0.524942 0.051 Uiso 1 1 calc R U . . .
H16B H 0.774680 0.841941 0.620439 0.051 Uiso 1 1 calc R U . . .
C31 C 0.5935(5) 0.3061(7) -0.0350(4) 0.0401(14) Uani 1 1 d . . . . .
H31 H 0.611296 0.218386 -0.008429 0.048 Uiso 1 1 calc R U . . .
C32 C 0.5021(5) 0.3215(7) -0.1194(4) 0.0433(15) Uani 1 1 d . . . . .
H32 H 0.458455 0.245199 -0.149937 0.052 Uiso 1 1 calc R U . . .
C33 C 0.4755(6) 0.4467(8) -0.1580(4) 0.0483(16) Uani 1 1 d . . . . .
H33 H 0.412623 0.458613 -0.215358 0.058 Uiso 1 1 calc R U . . .
C34 C 0.5410(5) 0.5569(7) -0.1129(4) 0.0450(16) Uani 1 1 d . . . . .
H34 H 0.524100 0.645226 -0.138661 0.054 Uiso 1 1 calc R U . . .
C35 C 0.6314(5) 0.5345(7) -0.0295(4) 0.0342(13) Uani 1 1 d . . . . .
C36 C 0.7123(5) 0.6365(6) 0.0244(4) 0.0349(14) Uani 1 1 d . . . . .
C41 C 0.8655(5) 0.7280(7) 0.1337(4) 0.0433(15) Uani 1 1 d . . . . .
H41X H 0.852491 0.748476 0.199502 0.052 Uiso 0.61(3) 1 calc R U P A 1
H41Y H 0.875397 0.747907 0.204524 0.052 Uiso 0.39(3) 1 calc R U P A 2
C42 C 0.7963(6) 0.8380(7) 0.0654(5) 0.0470(16) Uani 1 1 d . . . . .
H42 H 0.754769 0.896888 0.104152 0.056 Uiso 1 1 calc R U . . .
C43 C 0.8669(7) 0.9241(8) 0.0174(6) 0.066(2) Uani 1 1 d . . . . .
H43A H 0.883878 1.008673 0.055525 0.079 Uiso 0.61(3) 1 calc R U P A 1
H43B H 0.815003 0.948319 -0.047366 0.079 Uiso 0.61(3) 1 calc R U P A 1
H43C H 0.813601 0.985735 -0.029166 0.079 Uiso 0.39(3) 1 calc R U P A 2
H43D H 0.924743 0.978810 0.066000 0.079 Uiso 0.39(3) 1 calc R U P A 2
C44X C 0.9883(16) 0.8722(18) 0.0014(15) 0.062(5) Uani 0.61(3) 1 d D . P A 1
H44A H 0.972197 0.823076 -0.061389 0.075 Uiso 0.61(3) 1 calc R U P A 1
H44B H 1.039650 0.950802 -0.003803 0.075 Uiso 0.61(3) 1 calc R U P A 1
C45X C 1.0565(12) 0.7814(17) 0.0803(13) 0.061(4) Uani 0.61(3) 1 d D . P A 1
H45A H 1.084286 0.702074 0.049546 0.074 Uiso 0.61(3) 1 calc R U P A 1
H45B H 1.128951 0.829999 0.117301 0.074 Uiso 0.61(3) 1 calc R U P A 1
C46X C 0.9937(13) 0.736(2) 0.1452(15) 0.066(5) Uani 0.61(3) 1 d D . P A 1
H46A H 1.023887 0.791238 0.204629 0.080 Uiso 0.61(3) 1 calc R U P A 1
H46B H 1.023846 0.643760 0.162503 0.080 Uiso 0.61(3) 1 calc R U P A 1
C44Y C 0.924(4) 0.843(3) -0.0284(17) 0.084(10) Uani 0.39(3) 1 d D . P A 2
H44C H 0.972149 0.900213 -0.061951 0.100 Uiso 0.39(3) 1 calc R U P A 2
H44D H 0.862563 0.796989 -0.079694 0.100 Uiso 0.39(3) 1 calc R U P A 2
C45Y C 1.006(4) 0.738(3) 0.028(3) 0.099(14) Uani 0.39(3) 1 d D . P A 2
H45C H 1.010091 0.665620 -0.019753 0.119 Uiso 0.39(3) 1 calc R U P A 2
H45D H 1.087006 0.779028 0.046640 0.119 Uiso 0.39(3) 1 calc R U P A 2
C46Y C 0.9891(18) 0.676(3) 0.1075(19) 0.047(5) Uani 0.39(3) 1 d D . P A 2
H46C H 1.058748 0.694189 0.163302 0.056 Uiso 0.39(3) 1 calc R U P A 2
H46D H 0.984415 0.577203 0.096442 0.056 Uiso 0.39(3) 1 calc R U P A 2
C1S C 0.4201(6) 0.6531(7) 0.3354(5) 0.0511(17) Uani 1 1 d . . . . .
H1S H 0.486301 0.651982 0.300805 0.061 Uiso 1 1 calc R U . . .
Cl1S Cl 0.2881(2) 0.6013(4) 0.25493(19) 0.1094(10) Uani 1 1 d . . . . .
Cl2S Cl 0.45778(18) 0.5443(2) 0.43390(14) 0.0733(6) Uani 1 1 d . . . . .
Cl3S Cl 0.4056(3) 0.8180(3) 0.3769(3) 0.1120(10) Uani 1 1 d . . . . .


_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 N2 1.999(4) . ?
Cu1 N1 2.062(4) . ?
Cu1 Cl2 2.2427(15) . ?
Cu1 Cl1 2.2739(14) . ?
Cu2 N4 1.995(5) . ?
Cu2 N3 2.084(4) . ?
Cu2 Cl4 2.2327(18) . ?
Cu2 Cl3 2.2834(13) . ?
Cu2 Cl1 2.7173(16) . ?
O1 C6 1.327(6) . ?
O1 C12 1.483(7) . ?
O2 C36 1.328(7) . ?
O2 C42 1.475(7) . ?
N1 C1 1.325(7) . ?
N1 C5 1.351(7) . ?
N2 C6 1.266(7) . ?
N2 C11 1.486(7) . ?
N3 C31 1.331(7) . ?
N3 C35 1.353(8) . ?
N4 C36 1.271(7) . ?
N4 C41 1.475(7) . ?
C1 C2 1.390(8) . ?
C1 H1 0.9500 . ?
C2 C3 1.375(9) . ?
C2 H2 0.9500 . ?
C3 C4 1.385(8) . ?
C3 H3 0.9500 . ?
C4 C5 1.370(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.460(7) . ?
C11 C16 1.499(8) . ?
C11 C12 1.555(8) . ?
C11 H11 1.0000 . ?
C12 C13 1.491(9) . ?
C12 H12 1.0000 . ?
C13 C14 1.474(10) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.532(10) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.500(9) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C31 C32 1.386(8) . ?
C31 H31 0.9500 . ?
C32 C33 1.361(9) . ?
C32 H32 0.9500 . ?
C33 C34 1.388(9) . ?
C33 H33 0.9500 . ?
C34 C35 1.381(8) . ?
C34 H34 0.9500 . ?
C35 C36 1.453(8) . ?
C41 C46X 1.439(15) . ?
C41 C42 1.541(9) . ?
C41 C46Y 1.64(2) . ?
C41 H41X 1.0000 . ?
C41 H41Y 1.0000 . ?
C42 C43 1.456(9) . ?
C42 H42 1.0000 . ?
C43 C44Y 1.30(3) . ?
C43 C44X 1.553(17) . ?
C43 H43A 0.9900 . ?
C43 H43B 0.9900 . ?
C43 H43C 0.9900 . ?
C43 H43D 0.9900 . ?
C44X C45X 1.495(15) . ?
C44X H44A 0.9900 . ?
C44X H44B 0.9900 . ?
C45X C46X 1.375(15) . ?
C45X H45A 0.9900 . ?
C45X H45B 0.9900 . ?
C46X H46A 0.9900 . ?
C46X H46B 0.9900 . ?
C44Y C45Y 1.50(2) . ?
C44Y H44C 0.9900 . ?
C44Y H44D 0.9900 . ?
C45Y C46Y 1.344(19) . ?
C45Y H45C 0.9900 . ?
C45Y H45D 0.9900 . ?
C46Y H46C 0.9900 . ?
C46Y H46D 0.9900 . ?
C1S Cl1S 1.729(7) . ?
C1S Cl2S 1.731(7) . ?
C1S Cl3S 1.760(7) . ?
C1S H1S 1.0000 . ?

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
N2 Cu1 N1 79.74(17) . . ?
N2 Cu1 Cl2 91.78(13) . . ?
N1 Cu1 Cl2 171.35(13) . . ?
N2 Cu1 Cl1 165.99(15) . . ?
N1 Cu1 Cl1 94.46(13) . . ?
Cl2 Cu1 Cl1 94.18(5) . . ?
N4 Cu2 N3 79.83(19) . . ?
N4 Cu2 Cl4 163.61(15) . . ?
N3 Cu2 Cl4 91.69(15) . . ?
N4 Cu2 Cl3 92.38(14) . . ?
N3 Cu2 Cl3 172.19(15) . . ?
Cl4 Cu2 Cl3 96.00(6) . . ?
N4 Cu2 Cl1 96.60(15) . . ?
N3 Cu2 Cl1 88.61(13) . . ?
Cl4 Cu2 Cl1 97.20(7) . . ?
Cl3 Cu2 Cl1 91.77(5) . . ?
Cu1 Cl1 Cu2 90.12(5) . . ?
C6 O1 C12 106.1(4) . . ?
C36 O2 C42 105.4(5) . . ?
C1 N1 C5 117.9(5) . . ?
C1 N1 Cu1 128.3(4) . . ?
C5 N1 Cu1 112.9(3) . . ?
C6 N2 C11 109.3(4) . . ?
C6 N2 Cu1 113.8(4) . . ?
C11 N2 Cu1 136.9(3) . . ?
C31 N3 C35 118.3(5) . . ?
C31 N3 Cu2 129.1(4) . . ?
C35 N3 Cu2 112.3(4) . . ?
C36 N4 C41 108.0(5) . . ?
C36 N4 Cu2 113.6(4) . . ?
C41 N4 Cu2 138.2(4) . . ?
N1 C1 C2 121.8(5) . . ?
N1 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C3 C2 C1 119.8(5) . . ?
C3 C2 H2 120.1 . . ?
C1 C2 H2 120.1 . . ?
C2 C3 C4 118.7(5) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
C5 C4 C3 118.1(5) . . ?
C5 C4 H4 121.0 . . ?
C3 C4 H4 121.0 . . ?
N1 C5 C4 123.8(5) . . ?
N1 C5 C6 111.5(4) . . ?
C4 C5 C6 124.8(5) . . ?
N2 C6 O1 118.4(5) . . ?
N2 C6 C5 120.4(4) . . ?
O1 C6 C5 121.2(5) . . ?
N2 C11 C16 113.1(5) . . ?
N2 C11 C12 101.7(4) . . ?
C16 C11 C12 112.8(5) . . ?
N2 C11 H11 109.6 . . ?
C16 C11 H11 109.6 . . ?
C12 C11 H11 109.6 . . ?
O1 C12 C13 110.9(5) . . ?
O1 C12 C11 104.4(4) . . ?
C13 C12 C11 114.3(5) . . ?
O1 C12 H12 109.0 . . ?
C13 C12 H12 109.0 . . ?
C11 C12 H12 109.0 . . ?
C14 C13 C12 113.6(6) . . ?
C14 C13 H13A 108.8 . . ?
C12 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C12 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 C15 114.6(6) . . ?
C13 C14 H14A 108.6 . . ?
C15 C14 H14A 108.6 . . ?
C13 C14 H14B 108.6 . . ?
C15 C14 H14B 108.6 . . ?
H14A C14 H14B 107.6 . . ?
C16 C15 C14 113.6(6) . . ?
C16 C15 H15A 108.8 . . ?
C14 C15 H15A 108.8 . . ?
C16 C15 H15B 108.8 . . ?
C14 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
C11 C16 C15 112.4(6) . . ?
C11 C16 H16A 109.1 . . ?
C15 C16 H16A 109.1 . . ?
C11 C16 H16B 109.1 . . ?
C15 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
N3 C31 C32 122.1(6) . . ?
N3 C31 H31 118.9 . . ?
C32 C31 H31 118.9 . . ?
C33 C32 C31 119.5(6) . . ?
C33 C32 H32 120.3 . . ?
C31 C32 H32 120.3 . . ?
C32 C33 C34 119.5(5) . . ?
C32 C33 H33 120.2 . . ?
C34 C33 H33 120.2 . . ?
C35 C34 C33 118.1(6) . . ?
C35 C34 H34 121.0 . . ?
C33 C34 H34 121.0 . . ?
N3 C35 C34 122.5(6) . . ?
N3 C35 C36 111.9(5) . . ?
C34 C35 C36 125.5(6) . . ?
N4 C36 O2 119.0(5) . . ?
N4 C36 C35 121.0(5) . . ?
O2 C36 C35 120.1(5) . . ?
C46X C41 N4 123.6(12) . . ?
C46X C41 C42 112.4(7) . . ?
N4 C41 C42 102.7(4) . . ?
N4 C41 C46Y 96.4(11) . . ?
C42 C41 C46Y 114.9(8) . . ?
C46X C41 H41X 105.6 . . ?
N4 C41 H41X 105.6 . . ?
C42 C41 H41X 105.6 . . ?
N4 C41 H41Y 113.7 . . ?
C42 C41 H41Y 113.7 . . ?
C46Y C41 H41Y 113.7 . . ?
C43 C42 O2 111.3(6) . . ?
C43 C42 C41 116.8(6) . . ?
O2 C42 C41 104.4(5) . . ?
C43 C42 H42 108.0 . . ?
O2 C42 H42 108.0 . . ?
C41 C42 H42 108.0 . . ?
C44Y C43 C42 106.1(16) . . ?
C42 C43 C44X 119.7(8) . . ?
C42 C43 H43A 107.4 . . ?
C44X C43 H43A 107.4 . . ?
C42 C43 H43B 107.4 . . ?
C44X C43 H43B 107.4 . . ?
H43A C43 H43B 106.9 . . ?
C44Y C43 H43C 110.5 . . ?
C42 C43 H43C 110.5 . . ?
C44Y C43 H43D 110.5 . . ?
C42 C43 H43D 110.5 . . ?
H43C C43 H43D 108.7 . . ?
C45X C44X C43 114.3(11) . . ?
C45X C44X H44A 108.7 . . ?
C43 C44X H44A 108.7 . . ?
C45X C44X H44B 108.7 . . ?
C43 C44X H44B 108.7 . . ?
H44A C44X H44B 107.6 . . ?
C46X C45X C44X 115.6(12) . . ?
C46X C45X H45A 108.4 . . ?
C44X C45X H45A 108.4 . . ?
C46X C45X H45B 108.4 . . ?
C44X C45X H45B 108.4 . . ?
H45A C45X H45B 107.4 . . ?
C45X C46X C41 129.2(12) . . ?
C45X C46X H46A 105.0 . . ?
C41 C46X H46A 105.0 . . ?
C45X C46X H46B 105.0 . . ?
C41 C46X H46B 105.0 . . ?
H46A C46X H46B 105.8 . . ?
C43 C44Y C45Y 119.6(19) . . ?
C43 C44Y H44C 107.4 . . ?
C45Y C44Y H44C 107.4 . . ?
C43 C44Y H44D 107.4 . . ?
C45Y C44Y H44D 107.4 . . ?
H44C C44Y H44D 107.0 . . ?
C46Y C45Y C44Y 124(2) . . ?
C46Y C45Y H45C 106.2 . . ?
C44Y C45Y H45C 106.2 . . ?
C46Y C45Y H45D 106.2 . . ?
C44Y C45Y H45D 106.2 . . ?
H45C C45Y H45D 106.4 . . ?
C45Y C46Y C41 111.1(19) . . ?
C45Y C46Y H46C 109.4 . . ?
C41 C46Y H46C 109.4 . . ?
C45Y C46Y H46D 109.4 . . ?
C41 C46Y H46D 109.4 . . ?
H46C C46Y H46D 108.0 . . ?
Cl1S C1S Cl2S 110.3(4) . . ?
Cl1S C1S Cl3S 110.9(4) . . ?
Cl2S C1S Cl3S 109.6(4) . . ?
Cl1S C1S H1S 108.7 . . ?
Cl2S C1S H1S 108.7 . . ?
Cl3S C1S H1S 108.7 . . ?

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 -0.2(9) . . . . ?
Cu1 N1 C1 C2 167.9(5) . . . . ?
N1 C1 C2 C3 -1.7(11) . . . . ?
C1 C2 C3 C4 2.4(10) . . . . ?
C2 C3 C4 C5 -1.2(9) . . . . ?
C1 N1 C5 C4 1.5(8) . . . . ?
Cu1 N1 C5 C4 -168.5(5) . . . . ?
C1 N1 C5 C6 -178.0(5) . . . . ?
Cu1 N1 C5 C6 12.1(6) . . . . ?
C3 C4 C5 N1 -0.7(9) . . . . ?
C3 C4 C5 C6 178.6(6) . . . . ?
C11 N2 C6 O1 -2.0(8) . . . . ?
Cu1 N2 C6 O1 175.4(4) . . . . ?
C11 N2 C6 C5 177.2(5) . . . . ?
Cu1 N2 C6 C5 -5.5(7) . . . . ?
C12 O1 C6 N2 -0.4(7) . . . . ?
C12 O1 C6 C5 -179.6(5) . . . . ?
N1 C5 C6 N2 -4.7(8) . . . . ?
C4 C5 C6 N2 175.8(6) . . . . ?
N1 C5 C6 O1 174.4(5) . . . . ?
C4 C5 C6 O1 -5.0(9) . . . . ?
C6 N2 C11 C16 -118.0(5) . . . . ?
Cu1 N2 C11 C16 65.5(7) . . . . ?
C6 N2 C11 C12 3.3(6) . . . . ?
Cu1 N2 C11 C12 -173.2(4) . . . . ?
C6 O1 C12 C13 125.9(5) . . . . ?
C6 O1 C12 C11 2.5(6) . . . . ?
N2 C11 C12 O1 -3.3(6) . . . . ?
C16 C11 C12 O1 118.2(5) . . . . ?
N2 C11 C12 C13 -124.6(5) . . . . ?
C16 C11 C12 C13 -3.1(7) . . . . ?
O1 C12 C13 C14 -68.6(8) . . . . ?
C11 C12 C13 C14 49.0(8) . . . . ?
C12 C13 C14 C15 -43.9(10) . . . . ?
C13 C14 C15 C16 -6.4(11) . . . . ?
N2 C11 C16 C15 68.2(7) . . . . ?
C12 C11 C16 C15 -46.6(7) . . . . ?
C14 C15 C16 C11 52.3(9) . . . . ?
C35 N3 C31 C32 -0.7(9) . . . . ?
Cu2 N3 C31 C32 172.4(4) . . . . ?
N3 C31 C32 C33 -0.2(9) . . . . ?
C31 C32 C33 C34 0.6(10) . . . . ?
C32 C33 C34 C35 -0.1(10) . . . . ?
C31 N3 C35 C34 1.2(8) . . . . ?
Cu2 N3 C35 C34 -173.0(5) . . . . ?
C31 N3 C35 C36 -176.8(5) . . . . ?
Cu2 N3 C35 C36 9.0(6) . . . . ?
C33 C34 C35 N3 -0.8(9) . . . . ?
C33 C34 C35 C36 176.9(6) . . . . ?
C41 N4 C36 O2 -2.5(8) . . . . ?
Cu2 N4 C36 O2 173.9(5) . . . . ?
C41 N4 C36 C35 176.1(5) . . . . ?
Cu2 N4 C36 C35 -7.5(8) . . . . ?
C42 O2 C36 N4 -2.3(8) . . . . ?
C42 O2 C36 C35 179.1(5) . . . . ?
N3 C35 C36 N4 -1.3(8) . . . . ?
C34 C35 C36 N4 -179.2(6) . . . . ?
N3 C35 C36 O2 177.3(6) . . . . ?
C34 C35 C36 O2 -0.7(10) . . . . ?
C36 N4 C41 C46X -122.5(10) . . . . ?
Cu2 N4 C41 C46X 62.5(11) . . . . ?
C36 N4 C41 C42 5.8(7) . . . . ?
Cu2 N4 C41 C42 -169.2(5) . . . . ?
C36 N4 C41 C46Y -111.5(9) . . . . ?
Cu2 N4 C41 C46Y 73.4(10) . . . . ?
C36 O2 C42 C43 132.5(6) . . . . ?
C36 O2 C42 C41 5.7(7) . . . . ?
C46X C41 C42 C43 4.9(14) . . . . ?
N4 C41 C42 C43 -130.1(6) . . . . ?
C46Y C41 C42 C43 -26.8(14) . . . . ?
C46X C41 C42 O2 128.2(13) . . . . ?
N4 C41 C42 O2 -6.8(6) . . . . ?
C46Y C41 C42 O2 96.5(12) . . . . ?
O2 C42 C43 C44Y -64.5(19) . . . . ?
C41 C42 C43 C44Y 55.1(19) . . . . ?
O2 C42 C43 C44X -95.2(13) . . . . ?
C41 C42 C43 C44X 24.4(14) . . . . ?
C42 C43 C44X C45X -33.7(19) . . . . ?
C43 C44X C45X C46X 12(2) . . . . ?
C44X C45X C46X C41 21(3) . . . . ?
N4 C41 C46X C45X 94(2) . . . . ?
C42 C41 C46X C45X -30(3) . . . . ?
C42 C43 C44Y C45Y -58(3) . . . . ?
C43 C44Y C45Y C46Y 32(4) . . . . ?
C44Y C45Y C46Y C41 2(4) . . . . ?
N4 C41 C46Y C45Y 106(2) . . . . ?
C42 C41 C46Y C45Y -2(2) . . . . ?

_refine_diff_density_max         0.767
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.082


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHCl3, Et2O'
####################################################################### 
# 
# 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_lii009
_database_code_depnum_ccdc_archive 'CCDC 2094394'
loop_
_audit_author_name
_audit_author_address
'Yuqiao Zhou'
;College of Chemistry, Sichuan University, Chengdu, China
China
;
_audit_update_record             
;
2021-07-05 deposited with the CCDC.	2022-01-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C11 H14 Cl2 Cu N2 O), 2(C H Cl3)'
_chemical_formula_sum            'C24 H30 Cl10 Cu2 N4 O2'
_chemical_formula_weight         888.10

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'
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'
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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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. 
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   13.8291(4)
_cell_length_b                   9.7078(3)
_cell_length_c                   14.4138(4)
_cell_angle_alpha                90
_cell_angle_beta                 116.0830(10)
_cell_angle_gamma                90
_cell_volume                     1737.98(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9798
_cell_measurement_theta_min      3.41
_cell_measurement_theta_max      74.49

_exptl_crystal_description       flake
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.697
_exptl_crystal_F_000             892
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.538
_exptl_crystal_size_mid          0.307
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    8.840
_shelx_estimated_absorpt_T_min   0.087
_shelx_estimated_absorpt_T_max   0.443
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.0799
_exptl_absorpt_correction_T_max  0.5810
_exptl_absorpt_process_details   'SADABS (Krause et al., 2015)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 Venture Photon II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28083
_diffrn_reflns_av_unetI/netI     0.0427
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.414
_diffrn_reflns_theta_max         74.533
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.971
_reflns_number_total             6833
_reflns_number_gt                6661
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.841
_reflns_Friedel_fraction_max     0.935
_reflns_Friedel_fraction_full    0.956

_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. 
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELT (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
; 
 Refined as a 2-component inversion twin. 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0644P)²+0.9629P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
; 
 Refined as an inversion twin. 
;
_refine_ls_abs_structure_Flack   0.091(19)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         6833
_refine_ls_number_parameters     423
_refine_ls_number_restraints     32
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0402
_refine_ls_wR_factor_ref         0.1037
_refine_ls_wR_factor_gt          0.1009
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.148
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
Cu1A Cu 0.79203(5) 0.29951(7) 0.34592(5) 0.02423(16) Uani 1 1 d . . . . .
Cl1A Cl 0.80272(9) 0.51675(11) 0.30406(8) 0.0279(2) Uani 1 1 d . . . . .
Cl2A Cl 0.64904(8) 0.22752(13) 0.20396(8) 0.0294(2) Uani 1 1 d . . . . .
O1A O 0.9220(3) 0.2374(4) 0.6542(3) 0.0313(7) Uani 1 1 d . . . . .
N1A N 0.8450(3) 0.3335(4) 0.4975(3) 0.0260(8) Uani 1 1 d . . . . .
N2A N 0.8388(3) 0.1041(4) 0.3999(3) 0.0236(7) Uani 1 1 d . . . . .
C1A C 0.8331(4) -0.0073(5) 0.3450(4) 0.0270(9) Uani 1 1 d . . . . .
H1A H 0.804027 0.000035 0.271940 0.032 Uiso 1 1 calc R U . . .
C2A C 0.8683(4) -0.1336(6) 0.3908(4) 0.0308(10) Uani 1 1 d . . . . .
H2A H 0.862781 -0.212262 0.349597 0.037 Uiso 1 1 calc R U . . .
C3A C 0.9119(4) -0.1457(6) 0.4975(4) 0.0318(10) Uani 1 1 d . . . . .
H3A H 0.936159 -0.232429 0.530024 0.038 Uiso 1 1 calc R U . . .
C4A C 0.9195(3) -0.0290(5) 0.5558(4) 0.0262(9) Uani 1 1 d . . . . .
H4A H 0.949713 -0.033366 0.629006 0.031 Uiso 1 1 calc R U . . .
C5A C 0.8818(3) 0.0931(5) 0.5043(3) 0.0220(8) Uani 1 1 d . . . . .
C6A C 0.8820(3) 0.2259(5) 0.5525(3) 0.0236(9) Uani 1 1 d . . . . .
C7A C 0.9062(4) 0.3819(6) 0.6736(4) 0.0338(11) Uani 1 1 d . . . . .
H7AA H 0.976002 0.426352 0.717410 0.041 Uiso 1 1 calc R U . . .
H7AB H 0.858753 0.389332 0.708531 0.041 Uiso 1 1 calc R U . . .
C8A C 0.8535(4) 0.4496(5) 0.5663(3) 0.0284(10) Uani 1 1 d . . . . .
H8A H 0.903937 0.519814 0.561360 0.034 Uiso 1 1 calc R U . . .
C9A C 0.7465(6) 0.5168(9) 0.5403(6) 0.069(3) Uani 1 1 d D . . . .
H9AX H 0.733131 0.567808 0.475467 0.083 Uiso 0.54(2) 1 calc R U P A 1
H9AY H 0.715692 0.446007 0.570120 0.083 Uiso 0.46(2) 1 calc R U P A 2
C10A C 0.7603(5) 0.6339(7) 0.6150(5) 0.0425(13) Uani 1 1 d . . . . .
H10A H 0.690335 0.677428 0.596996 0.064 Uiso 1 1 calc R U . . .
H10B H 0.810301 0.702234 0.610707 0.064 Uiso 1 1 calc R U . . .
H10C H 0.789039 0.597575 0.685540 0.064 Uiso 1 1 calc R U . . .
C11X C 0.6588(8) 0.4336(17) 0.5081(11) 0.058(5) Uani 0.54(2) 1 d D . P A 1
H11A H 0.655197 0.376017 0.450876 0.087 Uiso 0.54(2) 1 calc R U P A 1
H11B H 0.593609 0.490133 0.484925 0.087 Uiso 0.54(2) 1 calc R U P A 1
H11C H 0.664277 0.374679 0.565454 0.087 Uiso 0.54(2) 1 calc R U P A 1
C11Y C 0.6564(9) 0.5323(17) 0.4412(10) 0.045(4) Uani 0.46(2) 1 d D . P A 2
H11D H 0.638316 0.442868 0.406240 0.067 Uiso 0.46(2) 1 calc R U P A 2
H11E H 0.674793 0.597537 0.399543 0.067 Uiso 0.46(2) 1 calc R U P A 2
H11F H 0.594546 0.567244 0.450126 0.067 Uiso 0.46(2) 1 calc R U P A 2
Cu1B Cu 0.79564(5) 0.20115(7) 0.09243(5) 0.02619(17) Uani 1 1 d . . . . .
Cl1B Cl 0.94368(9) 0.23456(13) 0.24061(9) 0.0357(3) Uani 1 1 d . . . . .
Cl2B Cl 0.82160(10) -0.02315(13) 0.08222(9) 0.0369(3) Uani 1 1 d . . . . .
O1B O 0.6543(3) 0.5604(4) -0.0283(3) 0.0352(8) Uani 1 1 d . . . . .
N1B N 0.6388(3) 0.1956(5) -0.0193(3) 0.0260(8) Uani 1 1 d . . . . .
N2B N 0.7775(3) 0.3978(4) 0.0509(3) 0.0255(8) Uani 1 1 d . . . . .
C1B C 0.5735(4) 0.0881(6) -0.0544(4) 0.0309(10) Uani 1 1 d . . . . .
H1B H 0.601531 -0.001712 -0.032346 0.037 Uiso 1 1 calc R U . . .
C2B C 0.4644(4) 0.1032(7) -0.1230(4) 0.0389(12) Uani 1 1 d . . . . .
H2B H 0.419532 0.024520 -0.148719 0.047 Uiso 1 1 calc R U . . .
C3B C 0.4236(4) 0.2318(7) -0.1522(5) 0.0424(13) Uani 1 1 d . . . . .
H3B H 0.349681 0.243736 -0.198248 0.051 Uiso 1 1 calc R U . . .
C4B C 0.4904(4) 0.3460(6) -0.1145(4) 0.0352(11) Uani 1 1 d . . . . .
H4B H 0.462980 0.436804 -0.132991 0.042 Uiso 1 1 calc R U . . .
C5B C 0.5975(4) 0.3233(5) -0.0497(4) 0.0274(9) Uani 1 1 d . . . . .
C6B C 0.6797(4) 0.4300(5) -0.0067(4) 0.0259(9) Uani 1 1 d . . . . .
C7B C 0.7549(4) 0.6362(6) 0.0317(5) 0.0360(11) Uani 1 1 d . . . . .
H7BA H 0.749948 0.689319 0.088061 0.043 Uiso 1 1 calc R U . . .
H7BB H 0.770618 0.700567 -0.013238 0.043 Uiso 1 1 calc R U . . .
C8B C 0.8420(4) 0.5253(5) 0.0754(3) 0.0267(9) Uani 1 1 d . . . . .
H8B H 0.881575 0.536020 0.152123 0.032 Uiso 1 1 calc R U . . .
C9B C 0.9233(4) 0.5226(5) 0.0293(4) 0.0275(9) Uani 1 1 d . . . . .
H9BA H 0.972421 0.442332 0.059905 0.033 Uiso 1 1 calc R U . . .
C10B C 0.9920(4) 0.6542(6) 0.0607(4) 0.0364(11) Uani 1 1 d . . . . .
H10D H 1.040461 0.655454 0.027524 0.055 Uiso 1 1 calc R U . . .
H10E H 1.034455 0.656089 0.135897 0.055 Uiso 1 1 calc R U . . .
H10F H 0.944788 0.735078 0.038686 0.055 Uiso 1 1 calc R U . . .
C11B C 0.8695(4) 0.5050(7) -0.0880(4) 0.0382(12) Uani 1 1 d . . . . .
H11G H 0.924836 0.500691 -0.113063 0.057 Uiso 1 1 calc R U . . .
H11H H 0.821772 0.583432 -0.120016 0.057 Uiso 1 1 calc R U . . .
H11I H 0.827434 0.419620 -0.106182 0.057 Uiso 1 1 calc R U . . .
Cl1X Cl 0.5734(7) 0.1500(17) 0.4641(5) 0.120(4) Uani 0.66(2) 1 d D . P B 1
Cl2X Cl 0.6158(6) -0.1265(14) 0.4108(11) 0.137(4) Uani 0.66(2) 1 d D . P B 1
Cl3X Cl 0.4188(3) 0.0075(9) 0.2843(4) 0.0500(14) Uani 0.66(2) 1 d D . P B 1
Cl1Y Cl 0.6028(10) 0.0631(16) 0.4899(8) 0.086(4) Uani 0.34(2) 1 d D . P B 2
Cl2Y Cl 0.5987(14) -0.1687(17) 0.3777(8) 0.114(6) Uani 0.34(2) 1 d D . P B 2
Cl3Y Cl 0.4261(12) 0.026(3) 0.2861(14) 0.092(6) Uani 0.34(2) 1 d D . P B 2
Cl4S Cl 0.81448(17) 0.9228(3) 0.7633(2) 0.0871(8) Uani 1 1 d . . . . .
Cl5S Cl 0.6812(2) 1.1580(2) 0.75492(17) 0.0727(6) Uani 1 1 d . . . . .
Cl6S Cl 0.61171(19) 0.8817(3) 0.7677(2) 0.0797(6) Uani 1 1 d . . . . .
C1S C 0.5576(6) 0.0207(11) 0.3640(6) 0.084(3) Uani 1 1 d D . . . .
H1SX H 0.591701 0.059188 0.321158 0.101 Uiso 0.66(2) 1 calc R U P B 1
H1SY H 0.598027 0.073616 0.332828 0.101 Uiso 0.34(2) 1 calc R U P B 2
C2S C 0.7219(5) 0.9918(8) 0.8033(5) 0.0494(15) Uani 1 1 d . . . . .
H2S H 0.758022 0.997657 0.880420 0.059 Uiso 1 1 calc R U . . .


_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
Cu1A N1A 2.003(4) . ?
Cu1A N2A 2.045(4) . ?
Cu1A Cl1A 2.2163(13) . ?
Cu1A Cl2A 2.2422(12) . ?
O1A C6A 1.325(5) . ?
O1A C7A 1.465(7) . ?
N1A C6A 1.275(6) . ?
N1A C8A 1.471(6) . ?
N2A C1A 1.322(6) . ?
N2A C5A 1.356(6) . ?
C1A C2A 1.376(7) . ?
C1A H1A 0.9500 . ?
C2A C3A 1.388(8) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.387(8) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.374(7) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.464(7) . ?
C7A C8A 1.537(7) . ?
C7A H7AA 0.9900 . ?
C7A H7AB 0.9900 . ?
C8A C9A 1.506(8) . ?
C8A H8A 1.0000 . ?
C9A C11X 1.358(15) . ?
C9A C11Y 1.431(12) . ?
C9A C10A 1.520(8) . ?
C9A H9AX 1.0000 . ?
C9A H9AY 1.0000 . ?
C10A H10A 0.9800 . ?
C10A H10B 0.9800 . ?
C10A H10C 0.9800 . ?
C11X H11A 0.9800 . ?
C11X H11B 0.9800 . ?
C11X H11C 0.9800 . ?
C11Y H11D 0.9800 . ?
C11Y H11E 0.9800 . ?
C11Y H11F 0.9800 . ?
Cu1B N2B 1.984(4) . ?
Cu1B N1B 2.057(4) . ?
Cu1B Cl2B 2.2222(14) . ?
Cu1B Cl1B 2.2390(12) . ?
O1B C6B 1.315(6) . ?
O1B C7B 1.472(6) . ?
N1B C1B 1.326(6) . ?
N1B C5B 1.354(7) . ?
N2B C6B 1.277(6) . ?
N2B C8B 1.475(6) . ?
C1B C2B 1.402(7) . ?
C1B H1B 0.9500 . ?
C2B C3B 1.359(10) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.391(8) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.378(7) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.459(7) . ?
C7B C8B 1.530(8) . ?
C7B H7BA 0.9900 . ?
C7B H7BB 0.9900 . ?
C8B C9B 1.537(6) . ?
C8B H8B 1.0000 . ?
C9B C11B 1.529(7) . ?
C9B C10B 1.536(7) . ?
C9B H9BA 1.0000 . ?
C10B H10D 0.9800 . ?
C10B H10E 0.9800 . ?
C10B H10F 0.9800 . ?
C11B H11G 0.9800 . ?
C11B H11H 0.9800 . ?
C11B H11I 0.9800 . ?
Cl1X C1S 1.851(12) . ?
Cl2X C1S 1.633(12) . ?
Cl3X C1S 1.755(8) . ?
Cl1Y C1S 1.690(11) . ?
Cl2Y C1S 1.909(15) . ?
Cl3Y C1S 1.666(14) . ?
Cl4S C2S 1.752(7) . ?
Cl5S C2S 1.749(8) . ?
Cl6S C2S 1.744(8) . ?
C1S H1SX 1.0000 . ?
C1S H1SY 1.0000 . ?
C2S H2S 1.0000 . ?

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
N1A Cu1A N2A 80.49(16) . . ?
N1A Cu1A Cl1A 95.97(12) . . ?
N2A Cu1A Cl1A 159.85(11) . . ?
N1A Cu1A Cl2A 143.09(13) . . ?
N2A Cu1A Cl2A 93.59(11) . . ?
Cl1A Cu1A Cl2A 100.70(5) . . ?
C6A O1A C7A 105.5(4) . . ?
C6A N1A C8A 108.5(4) . . ?
C6A N1A Cu1A 113.4(3) . . ?
C8A N1A Cu1A 138.1(3) . . ?
C1A N2A C5A 118.8(4) . . ?
C1A N2A Cu1A 127.2(3) . . ?
C5A N2A Cu1A 113.9(3) . . ?
N2A C1A C2A 121.7(4) . . ?
N2A C1A H1A 119.2 . . ?
C2A C1A H1A 119.2 . . ?
C1A C2A C3A 119.8(5) . . ?
C1A C2A H2A 120.1 . . ?
C3A C2A H2A 120.1 . . ?
C4A C3A C2A 118.8(5) . . ?
C4A C3A H3A 120.6 . . ?
C2A C3A H3A 120.6 . . ?
C5A C4A C3A 117.9(4) . . ?
C5A C4A H4A 121.0 . . ?
C3A C4A H4A 121.0 . . ?
N2A C5A C4A 122.9(4) . . ?
N2A C5A C6A 111.5(4) . . ?
C4A C5A C6A 125.6(4) . . ?
N1A C6A O1A 118.5(4) . . ?
N1A C6A C5A 120.6(4) . . ?
O1A C6A C5A 120.9(4) . . ?
O1A C7A C8A 105.2(4) . . ?
O1A C7A H7AA 110.7 . . ?
C8A C7A H7AA 110.7 . . ?
O1A C7A H7AB 110.7 . . ?
C8A C7A H7AB 110.7 . . ?
H7AA C7A H7AB 108.8 . . ?
N1A C8A C9A 112.6(4) . . ?
N1A C8A C7A 102.3(4) . . ?
C9A C8A C7A 114.5(5) . . ?
N1A C8A H8A 109.0 . . ?
C9A C8A H8A 109.0 . . ?
C7A C8A H8A 109.0 . . ?
C11X C9A C8A 117.4(8) . . ?
C11Y C9A C8A 128.6(8) . . ?
C11X C9A C10A 120.1(9) . . ?
C11Y C9A C10A 114.3(8) . . ?
C8A C9A C10A 110.1(5) . . ?
C11X C9A H9AX 101.9 . . ?
C8A C9A H9AX 101.9 . . ?
C10A C9A H9AX 101.9 . . ?
C11Y C9A H9AY 98.8 . . ?
C8A C9A H9AY 98.8 . . ?
C10A C9A H9AY 98.8 . . ?
C9A C10A H10A 109.5 . . ?
C9A C10A H10B 109.5 . . ?
H10A C10A H10B 109.5 . . ?
C9A C10A H10C 109.5 . . ?
H10A C10A H10C 109.5 . . ?
H10B C10A H10C 109.5 . . ?
C9A C11X H11A 109.5 . . ?
C9A C11X H11B 109.5 . . ?
H11A C11X H11B 109.5 . . ?
C9A C11X H11C 109.5 . . ?
H11A C11X H11C 109.5 . . ?
H11B C11X H11C 109.5 . . ?
C9A C11Y H11D 109.5 . . ?
C9A C11Y H11E 109.5 . . ?
H11D C11Y H11E 109.5 . . ?
C9A C11Y H11F 109.5 . . ?
H11D C11Y H11F 109.5 . . ?
H11E C11Y H11F 109.5 . . ?
N2B Cu1B N1B 80.73(17) . . ?
N2B Cu1B Cl2B 157.79(12) . . ?
N1B Cu1B Cl2B 93.91(13) . . ?
N2B Cu1B Cl1B 95.14(12) . . ?
N1B Cu1B Cl1B 163.32(12) . . ?
Cl2B Cu1B Cl1B 95.66(5) . . ?
C6B O1B C7B 104.9(4) . . ?
C1B N1B C5B 118.5(4) . . ?
C1B N1B Cu1B 128.7(4) . . ?
C5B N1B Cu1B 112.3(3) . . ?
C6B N2B C8B 107.9(4) . . ?
C6B N2B Cu1B 112.9(3) . . ?
C8B N2B Cu1B 138.8(3) . . ?
N1B C1B C2B 121.9(5) . . ?
N1B C1B H1B 119.1 . . ?
C2B C1B H1B 119.1 . . ?
C3B C2B C1B 119.1(5) . . ?
C3B C2B H2B 120.5 . . ?
C1B C2B H2B 120.5 . . ?
C2B C3B C4B 119.9(5) . . ?
C2B C3B H3B 120.1 . . ?
C4B C3B H3B 120.1 . . ?
C5B C4B C3B 117.9(5) . . ?
C5B C4B H4B 121.0 . . ?
C3B C4B H4B 121.0 . . ?
N1B C5B C4B 122.7(5) . . ?
N1B C5B C6B 111.9(4) . . ?
C4B C5B C6B 125.4(5) . . ?
N2B C6B O1B 119.1(5) . . ?
N2B C6B C5B 120.5(5) . . ?
O1B C6B C5B 120.4(4) . . ?
O1B C7B C8B 105.1(4) . . ?
O1B C7B H7BA 110.7 . . ?
C8B C7B H7BA 110.7 . . ?
O1B C7B H7BB 110.7 . . ?
C8B C7B H7BB 110.7 . . ?
H7BA C7B H7BB 108.8 . . ?
N2B C8B C7B 102.0(4) . . ?
N2B C8B C9B 111.2(4) . . ?
C7B C8B C9B 115.3(4) . . ?
N2B C8B H8B 109.4 . . ?
C7B C8B H8B 109.4 . . ?
C9B C8B H8B 109.4 . . ?
C11B C9B C10B 110.9(4) . . ?
C11B C9B C8B 112.8(4) . . ?
C10B C9B C8B 109.5(4) . . ?
C11B C9B H9BA 107.8 . . ?
C10B C9B H9BA 107.8 . . ?
C8B C9B H9BA 107.8 . . ?
C9B C10B H10D 109.5 . . ?
C9B C10B H10E 109.5 . . ?
H10D C10B H10E 109.5 . . ?
C9B C10B H10F 109.5 . . ?
H10D C10B H10F 109.5 . . ?
H10E C10B H10F 109.5 . . ?
C9B C11B H11G 109.5 . . ?
C9B C11B H11H 109.5 . . ?
H11G C11B H11H 109.5 . . ?
C9B C11B H11I 109.5 . . ?
H11G C11B H11I 109.5 . . ?
H11H C11B H11I 109.5 . . ?
Cl3Y C1S Cl1Y 119.7(9) . . ?
Cl2X C1S Cl3X 113.9(7) . . ?
Cl2X C1S Cl1X 113.8(6) . . ?
Cl3X C1S Cl1X 106.3(5) . . ?
Cl3Y C1S Cl2Y 106.8(10) . . ?
Cl1Y C1S Cl2Y 99.8(7) . . ?
Cl2X C1S H1SX 107.5 . . ?
Cl3X C1S H1SX 107.5 . . ?
Cl1X C1S H1SX 107.5 . . ?
Cl3Y C1S H1SY 110.0 . . ?
Cl1Y C1S H1SY 110.0 . . ?
Cl2Y C1S H1SY 110.0 . . ?
Cl6S C2S Cl5S 111.2(4) . . ?
Cl6S C2S Cl4S 109.8(4) . . ?
Cl5S C2S Cl4S 112.0(4) . . ?
Cl6S C2S H2S 107.9 . . ?
Cl5S C2S H2S 107.9 . . ?
Cl4S C2S H2S 107.9 . . ?

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
C5A N2A C1A C2A 0.9(7) . . . . ?
Cu1A N2A C1A C2A 179.4(3) . . . . ?
N2A C1A C2A C3A -0.6(7) . . . . ?
C1A C2A C3A C4A -0.3(7) . . . . ?
C2A C3A C4A C5A 0.8(7) . . . . ?
C1A N2A C5A C4A -0.4(6) . . . . ?
Cu1A N2A C5A C4A -179.1(3) . . . . ?
C1A N2A C5A C6A 179.8(4) . . . . ?
Cu1A N2A C5A C6A 1.1(4) . . . . ?
C3A C4A C5A N2A -0.5(7) . . . . ?
C3A C4A C5A C6A 179.3(4) . . . . ?
C8A N1A C6A O1A -2.1(6) . . . . ?
Cu1A N1A C6A O1A 178.2(3) . . . . ?
C8A N1A C6A C5A 178.8(4) . . . . ?
Cu1A N1A C6A C5A -1.0(5) . . . . ?
C7A O1A C6A N1A 2.2(6) . . . . ?
C7A O1A C6A C5A -178.6(4) . . . . ?
N2A C5A C6A N1A -0.1(6) . . . . ?
C4A C5A C6A N1A -179.9(4) . . . . ?
N2A C5A C6A O1A -179.2(4) . . . . ?
C4A C5A C6A O1A 0.9(7) . . . . ?
C6A O1A C7A C8A -1.3(5) . . . . ?
C6A N1A C8A C9A -122.5(6) . . . . ?
Cu1A N1A C8A C9A 57.1(8) . . . . ?
C6A N1A C8A C7A 1.0(5) . . . . ?
Cu1A N1A C8A C7A -179.4(4) . . . . ?
O1A C7A C8A N1A 0.2(5) . . . . ?
O1A C7A C8A C9A 122.4(5) . . . . ?
N1A C8A C9A C11X 36.7(11) . . . . ?
C7A C8A C9A C11X -79.7(10) . . . . ?
N1A C8A C9A C11Y -32.6(14) . . . . ?
C7A C8A C9A C11Y -149.0(11) . . . . ?
N1A C8A C9A C10A 179.0(6) . . . . ?
C7A C8A C9A C10A 62.6(9) . . . . ?
C5B N1B C1B C2B 1.3(7) . . . . ?
Cu1B N1B C1B C2B 172.7(4) . . . . ?
N1B C1B C2B C3B -1.8(8) . . . . ?
C1B C2B C3B C4B 0.5(8) . . . . ?
C2B C3B C4B C5B 1.3(8) . . . . ?
C1B N1B C5B C4B 0.7(7) . . . . ?
Cu1B N1B C5B C4B -172.2(4) . . . . ?
C1B N1B C5B C6B -178.6(4) . . . . ?
Cu1B N1B C5B C6B 8.6(4) . . . . ?
C3B C4B C5B N1B -2.0(7) . . . . ?
C3B C4B C5B C6B 177.2(5) . . . . ?
C8B N2B C6B O1B -3.1(6) . . . . ?
Cu1B N2B C6B O1B 170.9(3) . . . . ?
C8B N2B C6B C5B 175.7(4) . . . . ?
Cu1B N2B C6B C5B -10.3(6) . . . . ?
C7B O1B C6B N2B -3.8(6) . . . . ?
C7B O1B C6B C5B 177.4(4) . . . . ?
N1B C5B C6B N2B 0.9(6) . . . . ?
C4B C5B C6B N2B -178.3(5) . . . . ?
N1B C5B C6B O1B 179.7(4) . . . . ?
C4B C5B C6B O1B 0.5(7) . . . . ?
C6B O1B C7B C8B 8.6(5) . . . . ?
C6B N2B C8B C7B 8.1(5) . . . . ?
Cu1B N2B C8B C7B -163.4(4) . . . . ?
C6B N2B C8B C9B -115.3(4) . . . . ?
Cu1B N2B C8B C9B 73.2(6) . . . . ?
O1B C7B C8B N2B -10.0(5) . . . . ?
O1B C7B C8B C9B 110.7(4) . . . . ?
N2B C8B C9B C11B 58.5(6) . . . . ?
C7B C8B C9B C11B -56.9(6) . . . . ?
N2B C8B C9B C10B -177.5(4) . . . . ?
C7B C8B C9B C10B 67.0(5) . . . . ?

_refine_diff_density_max         0.628
_refine_diff_density_min         -1.038
_refine_diff_density_rms         0.095


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: CHCL3, Et2O'
