# 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_mht12pt10_sx
_audit_block_doi                 10.5517/ccdc.csd.cc25sryp
_database_code_depnum_ccdc_archive 'CCDC 2019803'
loop_
_citation_id
_citation_doi
_citation_year
1 10.26434/chemrxiv.12592418.v1 2020
loop_
_audit_author_name
_audit_author_address
'Peter Turner'
;University of Sydney
Australia
;
_audit_update_record             
;
2021-02-05 deposited with the CCDC.	2021-02-26 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         ?
_chemical_formula_sum            'C24 H40 Cl2 Cu N4 O10'
_chemical_formula_weight         679.04

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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14


_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.3223(9)
_cell_length_b                   16.8722(17)
_cell_length_c                   19.380(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.629(2)
_cell_angle_gamma                90
_cell_volume                     2996.0(5)
_cell_formula_units_Z            4

_cell_measurement_temperature    150.0(5)
_cell_measurement_reflns_used    9854
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      34.18

_exptl_crystal_description       prismatic
_exptl_crystal_colour            'dark violet'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_F_000             1420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.396
_exptl_crystal_size_mid          0.306
_exptl_crystal_size_min          0.242
_exptl_absorpt_coefficient_mu    0.967
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.921
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_process_details   
;
 SADABS (Sheldrick, 1996)
;

_diffrn_crystal_treatment        
;
attached with Exxon Paratone N, to a short length 
of fibre supported on a thin piece of copper wire 
inserted in a copper mounting pin.  The crystal was 
quenched in a cold nitrogen gas stream from an 
Oxford Cryosystems Cryostream. 
;

_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  APEXII-FR591
_diffrn_measurement_method       ω+φ
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            118853
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.138
_diffrn_reflns_theta_max         35.211
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             12932
_reflns_number_gt                10651
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'APEX (Bruker-AXS,2012)'
_computing_cell_refinement       'SAINT (Bruker-AXS,2012)'
_computing_data_reduction        'SAINT and XPREP (Bruker-AXS,2012)'
_computing_structure_solution    'SIR97 (Altomare, et. al. 1997)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
  OLEX2 (Dolomanov,O.V.et al., 2009)
  shelXle (Hübschle,C.B., et al., 2011) 
;

_computing_publication_material  
;    
  WinGX (Farrugia, 1999)
  PWT (Farrugia, 2013)
  PLATON (Spek, A.K., 2003) 
;

_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)+(0.07P)²+7.0P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         12932
_refine_ls_number_parameters     349
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0934
_refine_ls_R_factor_gt           0.0803
_refine_ls_wR_factor_ref         0.2107
_refine_ls_wR_factor_gt          0.2027
_refine_ls_goodness_of_fit_ref   1.172
_refine_ls_restrained_S_all      1.172
_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 0.58842(3) 0.24883(2) 0.35671(2) 0.02167(8) Uani 1 1 d . . . . .
O1 O 0.6723(2) 0.33509(15) 0.25984(11) 0.0337(4) Uani 1 1 d . . . . .
N1 N 0.7800(3) 0.30443(14) 0.40565(12) 0.0263(4) Uani 1 1 d . . . . .
N2 N 0.4535(3) 0.32521(13) 0.39639(12) 0.0253(4) Uani 1 1 d . . . . .
N3 N 0.3948(3) 0.19857(14) 0.30025(13) 0.0272(4) Uani 1 1 d . . . . .
N4 N 0.7155(3) 0.15006(14) 0.35193(12) 0.0269(4) Uani 1 1 d . . . . .
C1 C 0.7754(4) 0.3297(2) 0.47932(15) 0.0366(6) Uani 1 1 d . . . . .
H1A H 0.869132 0.355853 0.499016 0.044 Uiso 1 1 calc R U . . .
H1B H 0.767487 0.281766 0.507780 0.044 Uiso 1 1 calc R U . . .
C2 C 0.6520(4) 0.3857(2) 0.48724(15) 0.0348(6) Uani 1 1 d . . . . .
H2A H 0.669185 0.406289 0.535893 0.042 Uiso 1 1 calc R U . . .
H2B H 0.653471 0.431330 0.455300 0.042 Uiso 1 1 calc R U . . .
C3 C 0.5035(4) 0.34801(19) 0.47163(14) 0.0325(6) Uani 1 1 d . . . . .
H3A H 0.504559 0.300005 0.501086 0.039 Uiso 1 1 calc R U . . .
H3B H 0.431797 0.385382 0.485278 0.039 Uiso 1 1 calc R U . . .
C4 C 0.3191(3) 0.27692(19) 0.39371(18) 0.0344(6) Uani 1 1 d . . . . .
H4A H 0.240564 0.310132 0.406616 0.041 Uiso 1 1 calc R U . . .
H4B H 0.338719 0.232682 0.427699 0.041 Uiso 1 1 calc R U . . .
C5 C 0.2716(3) 0.24469(19) 0.32088(19) 0.0350(6) Uani 1 1 d . . . . .
H5A H 0.243422 0.288830 0.287465 0.042 Uiso 1 1 calc R U . . .
H5B H 0.185650 0.209808 0.319425 0.042 Uiso 1 1 calc R U . . .
C6 C 0.3784(4) 0.11437(17) 0.32153(18) 0.0343(6) Uani 1 1 d . . . . .
H6A H 0.286118 0.093296 0.294107 0.041 Uiso 1 1 calc R U . . .
H6B H 0.369572 0.113490 0.371655 0.041 Uiso 1 1 calc R U . . .
C7 C 0.5013(4) 0.05947(18) 0.31172(19) 0.0384(7) Uani 1 1 d . . . . .
H7A H 0.470032 0.004004 0.316613 0.046 Uiso 1 1 calc R U . . .
H7B H 0.520557 0.066050 0.263491 0.046 Uiso 1 1 calc R U . . .
C8 C 0.6405(4) 0.07391(18) 0.36316(18) 0.0365(6) Uani 1 1 d . . . . .
H8A H 0.618505 0.073899 0.411212 0.044 Uiso 1 1 calc R U . . .
H8B H 0.708398 0.029473 0.360064 0.044 Uiso 1 1 calc R U . . .
C9 C 0.8377(4) 0.1628(2) 0.41341(16) 0.0365(6) Uani 1 1 d . . . . .
H9A H 0.800516 0.157138 0.457808 0.044 Uiso 1 1 calc R U . . .
H9B H 0.914746 0.122498 0.412920 0.044 Uiso 1 1 calc R U . . .
C10 C 0.8998(3) 0.2438(2) 0.40910(17) 0.0348(6) Uani 1 1 d . . . . .
H10A H 0.944744 0.247891 0.366758 0.042 Uiso 1 1 calc R U . . .
H10B H 0.976523 0.253712 0.450827 0.042 Uiso 1 1 calc R U . . .
C11 C 0.8195(3) 0.37445(17) 0.36586(15) 0.0291(5) Uani 1 1 d . . . . .
H11A H 0.752452 0.418722 0.370889 0.035 Uiso 1 1 calc R U . . .
H11B H 0.919753 0.391582 0.386546 0.035 Uiso 1 1 calc R U . . .
C12 C 0.8118(3) 0.35747(16) 0.28980(15) 0.0273(5) Uani 1 1 d . . . . .
C13 C 0.9237(4) 0.3648(2) 0.25624(19) 0.0388(7) Uani 1 1 d D . . . .
H13A H 0.910472 0.354152 0.207336 0.047 Uiso 1 1 calc R U . . .
H13B H 1.016682 0.380633 0.281225 0.047 Uiso 1 1 calc R U . . .
C14 C 0.6438(5) 0.3347(3) 0.18435(18) 0.0570(12) Uani 1 1 d . . . . .
H14A H 0.679840 0.384041 0.167057 0.085 Uiso 1 1 calc R U . . .
H14B H 0.538447 0.330258 0.167076 0.085 Uiso 1 1 calc R U . . .
H14C H 0.693598 0.289490 0.167472 0.085 Uiso 1 1 calc R U . . .
C15 C 0.4248(3) 0.39733(16) 0.35079(15) 0.0278(5) Uani 1 1 d . . . . .
H15A H 0.512899 0.431273 0.358713 0.033 Uiso 1 1 calc R U . . .
H15B H 0.406305 0.380697 0.300949 0.033 Uiso 1 1 calc R U . . .
C16 C 0.3001(3) 0.44389(19) 0.36428(17) 0.0331(6) Uani 1 1 d . . . . .
C17 C 0.1989(4) 0.4805(2) 0.3766(2) 0.0406(7) Uani 1 1 d . . . . .
H17 H 0.117950 0.509819 0.386448 0.049 Uiso 1 1 calc R U . . .
C18 C 0.3788(3) 0.20476(19) 0.22207(16) 0.0309(5) Uani 1 1 d . . . . .
H18A H 0.393659 0.260540 0.209187 0.037 Uiso 1 1 calc R U . . .
H18B H 0.455173 0.172248 0.206385 0.037 Uiso 1 1 calc R U . . .
C19 C 0.2348(4) 0.1781(2) 0.18570(18) 0.0373(6) Uani 1 1 d . . . . .
C20 C 0.1149(4) 0.1581(3) 0.1613(2) 0.0477(9) Uani 1 1 d . . . . .
H20 H 0.018323 0.142035 0.141686 0.057 Uiso 1 1 calc R U . . .
C21 C 0.7748(3) 0.14518(17) 0.28524(14) 0.0287(5) Uani 1 1 d . . . . .
H21A H 0.693565 0.134159 0.245737 0.034 Uiso 1 1 calc R U . . .
H21B H 0.817514 0.197052 0.276317 0.034 Uiso 1 1 calc R U . . .
C22 C 0.8871(4) 0.0831(2) 0.28744(17) 0.0355(6) Uani 1 1 d . . . . .
C23 C 0.9785(5) 0.0340(2) 0.2909(2) 0.0489(9) Uani 1 1 d . . . . .
H23 H 1.052022 -0.005471 0.293702 0.059 Uiso 1 1 calc R U . . .
Cl1A Cl 0.6980(4) 0.10850(19) 0.08728(18) 0.0220(4) Uiso 0.3 1 d G . P A 1
O2A O 0.5882(8) 0.0818(5) 0.1236(4) 0.0360(9) Uiso 0.3 1 d G . P A 1
O3A O 0.8137(7) 0.0524(4) 0.0942(3) 0.0360(9) Uiso 0.3 1 d G . P A 1
O4A O 0.7507(7) 0.1833(3) 0.1155(4) 0.0360(9) Uiso 0.3 1 d G . P A 1
O5A O 0.6336(7) 0.1191(4) 0.0150(2) 0.0360(9) Uiso 0.3 1 d G . P A 1
Cl1B Cl 0.6775(6) 0.1735(3) 0.0471(3) 0.0220(4) Uiso 0.1 1 d G . P B 2
O2B O 0.7938(12) 0.1799(10) 0.0094(8) 0.0360(9) Uiso 0.1 1 d G . P B 2
O3B O 0.688(2) 0.1008(6) 0.0849(9) 0.0360(9) Uiso 0.1 1 d G . P B 2
O4B O 0.5428(10) 0.1778(11) -0.0015(7) 0.0360(9) Uiso 0.1 1 d G . P B 2
O5B O 0.6854(18) 0.2393(7) 0.0942(8) 0.0360(9) Uiso 0.1 1 d G . P B 2
Cl1C Cl 0.6621(2) 0.09452(12) 0.07551(10) 0.0155(4) Uiso 0.3 1 d G . P C 3
O2C O 0.8115(3) 0.0648(3) 0.1014(3) 0.0339(9) Uiso 0.3 1 d G . P C 3
O3C O 0.5876(6) 0.0408(3) 0.0261(2) 0.0339(9) Uiso 0.3 1 d G . P C 3
O4C O 0.6612(7) 0.1574(3) 0.0204(2) 0.0339(9) Uiso 0.3 1 d G . P C 3
O5C O 0.5776(6) 0.1086(4) 0.1288(2) 0.0339(9) Uiso 0.3 1 d G . P C 3
Cl1D Cl 0.6786(4) 0.1128(3) 0.0782(2) 0.0180(8) Uiso 0.2 1 d G . P D 4
O2D O 0.6240(10) 0.0764(5) 0.0126(3) 0.0417(15) Uiso 0.2 1 d G . P D 4
O3D O 0.7167(11) 0.1930(3) 0.0681(5) 0.0417(15) Uiso 0.2 1 d G . P D 4
O4D O 0.8028(8) 0.0693(5) 0.1123(5) 0.0417(15) Uiso 0.2 1 d G . P D 4
O5D O 0.5683(9) 0.1086(6) 0.1204(5) 0.0417(15) Uiso 0.2 1 d G . P D 4
Cl1E Cl 0.6992(10) 0.1192(5) 0.0899(4) 0.0220(4) Uiso 0.1 1 d G . P E 5
O2E O 0.7766(18) 0.1851(7) 0.1237(8) 0.026 Uiso 0.1 1 d G U P E 5
O3E O 0.6007(19) 0.0890(12) 0.1314(8) 0.026 Uiso 0.1 1 d G U P E 5
O4E O 0.8018(18) 0.0599(8) 0.0793(9) 0.026 Uiso 0.1 1 d G U P E 5
O5E O 0.6217(16) 0.1444(9) 0.0229(6) 0.026 Uiso 0.1 1 d G U P E 5
Cl2A Cl 0.7072(4) 0.1124(2) 0.6051(2) 0.0472(8) Uiso 0.4 1 d G . P F 1
O6A O 0.6978(8) 0.0374(2) 0.5715(4) 0.0560(10) Uiso 0.4 1 d G . P F 1
O7A O 0.8184(6) 0.1590(4) 0.5838(4) 0.0560(10) Uiso 0.4 1 d G . P F 1
O8A O 0.5692(5) 0.1510(4) 0.5873(4) 0.0560(10) Uiso 0.4 1 d G . P F 1
O9A O 0.7384(9) 0.0999(5) 0.6793(2) 0.0560(10) Uiso 0.4 1 d G . P F 1
Cl2B Cl 0.7428(6) 0.0951(3) 0.6009(3) 0.0472(8) Uiso 0.2 1 d G . P G 2
O6B O 0.8569(10) 0.0533(7) 0.5775(7) 0.059(2) Uiso 0.2 1 d DG . P G 2
O7B O 0.6069(9) 0.0565(7) 0.5775(7) 0.059(2) Uiso 0.2 1 d G . P G 2
O8B O 0.7747(15) 0.0990(9) 0.6756(3) 0.059(2) Uiso 0.2 1 d G . P G 2
O9B O 0.7390(14) 0.1740(4) 0.5737(7) 0.059(2) Uiso 0.2 1 d G . P G 2
Cl2C Cl 0.6920(5) 0.1040(2) 0.5885(2) 0.0310(7) Uiso 0.2 1 d G . P H 3
O6C O 0.8392(6) 0.1041(9) 0.5789(7) 0.072(3) Uiso 0.2 1 d G . P H 3
O7C O 0.6852(16) 0.1184(8) 0.6602(3) 0.072(3) Uiso 0.2 1 d G . P H 3
O8C O 0.6142(14) 0.1637(6) 0.5447(6) 0.072(3) Uiso 0.2 1 d G . P H 3
O9C O 0.6294(15) 0.0287(4) 0.5668(7) 0.072(3) Uiso 0.2 1 d G . P H 3
Cl2D Cl 0.7175(7) 0.1089(4) 0.6029(4) 0.0310(7) Uiso 0.2 1 d G . P I 4
O6D O 0.7799(13) 0.1817(5) 0.5865(9) 0.055(2) Uiso 0.2 1 d G . P I 4
O7D O 0.5636(6) 0.1103(8) 0.5796(7) 0.055(2) Uiso 0.2 1 d G . P I 4
O8D O 0.7817(13) 0.0461(6) 0.5700(7) 0.055(2) Uiso 0.2 1 d G . P I 4
O9D O 0.7521(17) 0.0978(10) 0.6773(4) 0.055(2) Uiso 0.2 1 d G . P I 4
O1M O 0.8162(4) -0.11560(18) 0.55056(15) 0.0504(7) Uani 1 1 d . . . . .
H1M H 0.824600 -0.067936 0.563188 0.076 Uiso 1 1 calc R U . . .
C1M C 0.8005(6) -0.1201(3) 0.4773(2) 0.0563(11) Uani 1 1 d . . . . .
H1M1 H 0.794391 -0.175773 0.462689 0.085 Uiso 1 1 calc R U . . .
H1M2 H 0.884821 -0.095178 0.462472 0.085 Uiso 1 1 calc R U . . .
H1M3 H 0.711137 -0.092391 0.455454 0.085 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
Cu1 N2 2.047(2) . ?
Cu1 N4 2.057(2) . ?
Cu1 N1 2.084(2) . ?
Cu1 N3 2.109(2) . ?
Cu1 O1 2.607(2) . ?
Cu1 O8C 3.883(10) . ?
O1 C12 1.376(3) . ?
O1 C14 1.438(4) . ?
N1 C11 1.493(4) . ?
N1 C1 1.498(4) . ?
N1 C10 1.508(4) . ?
N2 C4 1.487(4) . ?
N2 C3 1.497(4) . ?
N2 C15 1.499(4) . ?
N3 C6 1.495(4) . ?
N3 C18 1.498(4) . ?
N3 C5 1.502(4) . ?
N4 C8 1.498(4) . ?
N4 C21 1.499(3) . ?
N4 C9 1.504(4) . ?
C1 C2 1.518(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.502(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.501(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.513(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.503(5) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.492(5) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.490(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.333(4) . ?
C13 H13A 0.9500 . ?
C13 H13B 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.466(4) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.189(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.467(4) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.180(5) . ?
C20 H20 0.9500 . ?
C21 C22 1.476(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.181(5) . ?
C23 H23 0.9500 . ?
Cl1A O2A 1.4189 . ?
Cl1A O3A 1.4222 . ?
Cl1A O4A 1.4256 . ?
Cl1A O5A 1.4294 . ?
Cl1B O2B 1.4189 . ?
Cl1B O3B 1.4222 . ?
Cl1B O4B 1.4257 . ?
Cl1B O5B 1.4293 . ?
Cl1C O3C 1.4052 . ?
Cl1C O5C 1.4292 . ?
Cl1C O2C 1.4777 . ?
Cl1C O4C 1.5045 . ?
Cl1D O2D 1.4189 . ?
Cl1D O3D 1.4222 . ?
Cl1D O4D 1.4257 . ?
Cl1D O5D 1.4293 . ?
Cl1E O2E 1.4189 . ?
Cl1E O3E 1.4223 . ?
Cl1E O4E 1.4256 . ?
Cl1E O5E 1.4293 . ?
Cl2A O6A 1.4189 . ?
Cl2A O7A 1.4223 . ?
Cl2A O8A 1.4256 . ?
Cl2A O9A 1.4294 . ?
Cl2B O6B 1.4189 . ?
Cl2B O7B 1.4222 . ?
Cl2B O8B 1.4258 . ?
Cl2B O9B 1.4293 . ?
Cl2C O6C 1.4189 . ?
Cl2C O7C 1.4222 . ?
Cl2C O8C 1.4256 . ?
Cl2C O9C 1.4292 . ?
Cl2D O6D 1.4190 . ?
Cl2D O7D 1.4222 . ?
Cl2D O8D 1.4257 . ?
Cl2D O9D 1.4292 . ?
O1M C1M 1.403(5) . ?
O1M H1M 0.8400 . ?
C1M H1M1 0.9800 . ?
C1M H1M2 0.9800 . ?
C1M H1M3 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
N2 Cu1 N4 157.80(9) . . ?
N2 Cu1 N1 94.59(9) . . ?
N4 Cu1 N1 86.14(10) . . ?
N2 Cu1 N3 85.51(9) . . ?
N4 Cu1 N3 95.51(10) . . ?
N1 Cu1 N3 175.42(9) . . ?
N2 Cu1 O1 101.87(9) . . ?
N4 Cu1 O1 99.69(8) . . ?
N1 Cu1 O1 74.39(8) . . ?
N3 Cu1 O1 101.10(8) . . ?
N2 Cu1 O8C 79.41(18) . . ?
N4 Cu1 O8C 78.81(18) . . ?
N1 Cu1 O8C 80.8(2) . . ?
N3 Cu1 O8C 103.7(2) . . ?
O1 Cu1 O8C 155.2(2) . . ?
C12 O1 C14 114.4(2) . . ?
C12 O1 Cu1 103.59(16) . . ?
C14 O1 Cu1 134.9(2) . . ?
C11 N1 C1 108.6(2) . . ?
C11 N1 C10 108.0(2) . . ?
C1 N1 C10 107.6(2) . . ?
C11 N1 Cu1 113.15(17) . . ?
C1 N1 Cu1 112.91(19) . . ?
C10 N1 Cu1 106.28(18) . . ?
C4 N2 C3 106.5(2) . . ?
C4 N2 C15 111.5(2) . . ?
C3 N2 C15 110.8(2) . . ?
C4 N2 Cu1 102.36(16) . . ?
C3 N2 Cu1 115.16(19) . . ?
C15 N2 Cu1 110.18(15) . . ?
C6 N3 C18 110.4(2) . . ?
C6 N3 C5 107.3(2) . . ?
C18 N3 C5 107.1(2) . . ?
C6 N3 Cu1 111.1(2) . . ?
C18 N3 Cu1 114.38(16) . . ?
C5 N3 Cu1 106.10(16) . . ?
C8 N4 C21 109.5(2) . . ?
C8 N4 C9 108.3(2) . . ?
C21 N4 C9 110.2(2) . . ?
C8 N4 Cu1 113.60(19) . . ?
C21 N4 Cu1 112.98(17) . . ?
C9 N4 Cu1 101.95(17) . . ?
N1 C1 C2 115.4(3) . . ?
N1 C1 H1A 108.4 . . ?
C2 C1 H1A 108.4 . . ?
N1 C1 H1B 108.4 . . ?
C2 C1 H1B 108.4 . . ?
H1A C1 H1B 107.5 . . ?
C3 C2 C1 113.8(3) . . ?
C3 C2 H2A 108.8 . . ?
C1 C2 H2A 108.8 . . ?
C3 C2 H2B 108.8 . . ?
C1 C2 H2B 108.8 . . ?
H2A C2 H2B 107.7 . . ?
N2 C3 C2 114.5(2) . . ?
N2 C3 H3A 108.6 . . ?
C2 C3 H3A 108.6 . . ?
N2 C3 H3B 108.6 . . ?
C2 C3 H3B 108.6 . . ?
H3A C3 H3B 107.6 . . ?
N2 C4 C5 109.4(2) . . ?
N2 C4 H4A 109.8 . . ?
C5 C4 H4A 109.8 . . ?
N2 C4 H4B 109.8 . . ?
C5 C4 H4B 109.8 . . ?
H4A C4 H4B 108.2 . . ?
C4 C5 N3 109.3(3) . . ?
C4 C5 H5A 109.8 . . ?
N3 C5 H5A 109.8 . . ?
C4 C5 H5B 109.8 . . ?
N3 C5 H5B 109.8 . . ?
H5A C5 H5B 108.3 . . ?
N3 C6 C7 115.4(2) . . ?
N3 C6 H6A 108.4 . . ?
C7 C6 H6A 108.4 . . ?
N3 C6 H6B 108.4 . . ?
C7 C6 H6B 108.4 . . ?
H6A C6 H6B 107.5 . . ?
C8 C7 C6 113.5(3) . . ?
C8 C7 H7A 108.9 . . ?
C6 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
C6 C7 H7B 108.9 . . ?
H7A C7 H7B 107.7 . . ?
N4 C8 C7 114.3(3) . . ?
N4 C8 H8A 108.7 . . ?
C7 C8 H8A 108.7 . . ?
N4 C8 H8B 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C10 C9 N4 109.4(2) . . ?
C10 C9 H9A 109.8 . . ?
N4 C9 H9A 109.8 . . ?
C10 C9 H9B 109.8 . . ?
N4 C9 H9B 109.8 . . ?
H9A C9 H9B 108.3 . . ?
C9 C10 N1 109.4(3) . . ?
C9 C10 H10A 109.8 . . ?
N1 C10 H10A 109.8 . . ?
C9 C10 H10B 109.8 . . ?
N1 C10 H10B 109.8 . . ?
H10A C10 H10B 108.2 . . ?
C12 C11 N1 112.8(2) . . ?
C12 C11 H11A 109.0 . . ?
N1 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
N1 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 O1 125.7(3) . . ?
C13 C12 C11 124.4(3) . . ?
O1 C12 C11 109.9(2) . . ?
C12 C13 H13A 120.0 . . ?
C12 C13 H13B 120.0 . . ?
H13A C13 H13B 120.0 . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 N2 113.0(2) . . ?
C16 C15 H15A 109.0 . . ?
N2 C15 H15A 109.0 . . ?
C16 C15 H15B 109.0 . . ?
N2 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C17 C16 C15 178.4(4) . . ?
C16 C17 H17 180.0 . . ?
C19 C18 N3 112.1(2) . . ?
C19 C18 H18A 109.2 . . ?
N3 C18 H18A 109.2 . . ?
C19 C18 H18B 109.2 . . ?
N3 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C20 C19 C18 174.6(4) . . ?
C19 C20 H20 180.0 . . ?
C22 C21 N4 112.7(2) . . ?
C22 C21 H21A 109.0 . . ?
N4 C21 H21A 109.0 . . ?
C22 C21 H21B 109.0 . . ?
N4 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
C23 C22 C21 178.3(4) . . ?
C22 C23 H23 180.0 . . ?
O2A Cl1A O3A 110.3 . . ?
O2A Cl1A O4A 108.6 . . ?
O3A Cl1A O4A 110.6 . . ?
O2A Cl1A O5A 108.3 . . ?
O3A Cl1A O5A 110.5 . . ?
O4A Cl1A O5A 108.5 . . ?
O2B Cl1B O3B 110.3 . . ?
O2B Cl1B O4B 108.6 . . ?
O3B Cl1B O4B 110.6 . . ?
O2B Cl1B O5B 108.3 . . ?
O3B Cl1B O5B 110.5 . . ?
O4B Cl1B O5B 108.5 . . ?
O3C Cl1C O5C 109.3 . . ?
O3C Cl1C O2C 109.2 . . ?
O5C Cl1C O2C 115.0 . . ?
O3C Cl1C O4C 91.9 . . ?
O5C Cl1C O4C 117.6 . . ?
O2C Cl1C O4C 111.2 . . ?
O2D Cl1D O3D 110.3 . . ?
O2D Cl1D O4D 108.6 . . ?
O3D Cl1D O4D 110.6 . . ?
O2D Cl1D O5D 108.3 . . ?
O3D Cl1D O5D 110.5 . . ?
O4D Cl1D O5D 108.5 . . ?
O2E Cl1E O3E 110.3 . . ?
O2E Cl1E O4E 108.6 . . ?
O3E Cl1E O4E 110.6 . . ?
O2E Cl1E O5E 108.3 . . ?
O3E Cl1E O5E 110.5 . . ?
O4E Cl1E O5E 108.5 . . ?
O6A Cl2A O7A 110.3 . . ?
O6A Cl2A O8A 108.6 . . ?
O7A Cl2A O8A 110.6 . . ?
O6A Cl2A O9A 108.3 . . ?
O7A Cl2A O9A 110.5 . . ?
O8A Cl2A O9A 108.5 . . ?
O6B Cl2B O7B 110.3 . . ?
O6B Cl2B O8B 108.6 . . ?
O7B Cl2B O8B 110.6 . . ?
O6B Cl2B O9B 108.3 . . ?
O7B Cl2B O9B 110.5 . . ?
O8B Cl2B O9B 108.5 . . ?
O6C Cl2C O7C 110.3 . . ?
O6C Cl2C O8C 108.6 . . ?
O7C Cl2C O8C 110.6 . . ?
O6C Cl2C O9C 108.3 . . ?
O7C Cl2C O9C 110.5 . . ?
O8C Cl2C O9C 108.5 . . ?
Cl2C O8C Cu1 139.2(7) . . ?
O6D Cl2D O7D 110.3 . . ?
O6D Cl2D O8D 108.6 . . ?
O7D Cl2D O8D 110.5 . . ?
O6D Cl2D O9D 108.3 . . ?
O7D Cl2D O9D 110.5 . . ?
O8D Cl2D O9D 108.5 . . ?
C1M O1M H1M 109.5 . . ?
O1M C1M H1M1 109.5 . . ?
O1M C1M H1M2 109.5 . . ?
H1M1 C1M H1M2 109.5 . . ?
O1M C1M H1M3 109.5 . . ?
H1M1 C1M H1M3 109.5 . . ?
H1M2 C1M H1M3 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
C11 N1 C1 C2 68.5(3) . . . . ?
C10 N1 C1 C2 -174.8(3) . . . . ?
Cu1 N1 C1 C2 -57.8(3) . . . . ?
N1 C1 C2 C3 68.8(4) . . . . ?
C4 N2 C3 C2 170.3(3) . . . . ?
C15 N2 C3 C2 -68.3(3) . . . . ?
Cu1 N2 C3 C2 57.6(3) . . . . ?
C1 C2 C3 N2 -67.4(4) . . . . ?
C3 N2 C4 C5 -174.1(3) . . . . ?
C15 N2 C4 C5 65.0(3) . . . . ?
Cu1 N2 C4 C5 -52.8(3) . . . . ?
N2 C4 C5 N3 56.0(3) . . . . ?
C6 N3 C5 C4 90.9(3) . . . . ?
C18 N3 C5 C4 -150.5(2) . . . . ?
Cu1 N3 C5 C4 -27.9(3) . . . . ?
C18 N3 C6 C7 69.4(3) . . . . ?
C5 N3 C6 C7 -174.2(3) . . . . ?
Cu1 N3 C6 C7 -58.6(3) . . . . ?
N3 C6 C7 C8 71.6(4) . . . . ?
C21 N4 C8 C7 -69.0(3) . . . . ?
C9 N4 C8 C7 170.8(3) . . . . ?
Cu1 N4 C8 C7 58.4(3) . . . . ?
C6 C7 C8 N4 -70.0(3) . . . . ?
C8 N4 C9 C10 -171.5(3) . . . . ?
C21 N4 C9 C10 68.8(3) . . . . ?
Cu1 N4 C9 C10 -51.4(3) . . . . ?
N4 C9 C10 N1 56.2(3) . . . . ?
C11 N1 C10 C9 -151.1(2) . . . . ?
C1 N1 C10 C9 91.8(3) . . . . ?
Cu1 N1 C10 C9 -29.4(3) . . . . ?
C1 N1 C11 C12 -174.0(2) . . . . ?
C10 N1 C11 C12 69.6(3) . . . . ?
Cu1 N1 C11 C12 -47.8(3) . . . . ?
C14 O1 C12 C13 -12.1(5) . . . . ?
Cu1 O1 C12 C13 143.1(3) . . . . ?
C14 O1 C12 C11 166.6(3) . . . . ?
Cu1 O1 C12 C11 -38.2(2) . . . . ?
N1 C11 C12 C13 -121.4(3) . . . . ?
N1 C11 C12 O1 59.9(3) . . . . ?
C4 N2 C15 C16 51.4(3) . . . . ?
C3 N2 C15 C16 -67.0(3) . . . . ?
Cu1 N2 C15 C16 164.34(19) . . . . ?
C6 N3 C18 C19 61.0(3) . . . . ?
C5 N3 C18 C19 -55.5(3) . . . . ?
Cu1 N3 C18 C19 -172.8(2) . . . . ?
C8 N4 C21 C22 -63.0(3) . . . . ?
C9 N4 C21 C22 56.0(3) . . . . ?
Cu1 N4 C21 C22 169.3(2) . . . . ?
O6C Cl2C O8C Cu1 40.5(11) . . . . ?
O7C Cl2C O8C Cu1 161.6(11) . . . . ?
O9C Cl2C O8C Cu1 -77.1(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1A O5A^a 0.99 2.46 3.39(4) 156.4 4_666 yes
C1 H1A Cl1B^b 0.99 2.90 3.736(6) 143.2 4_666 yes
C1 H1A O4B^b 0.99 1.72 2.45(9) 128.1 4_666 yes
C1 H1A Cl1C^c 0.99 2.98 3.953(4) 168.6 4_666 yes
C1 H1A O2D^d 0.99 2.61 3.57(7) 163.2 4_666 yes
C1 H1B O7A^a 0.99 2.54 3.501(8) 165.1 . yes
C1 H1B O9B^b 0.99 2.27 3.255(8) 177.3 . yes
C1 H1B O8C^c 0.99 2.63 3.524(13) 150.7 . yes
C1 H1B O6D^d 0.99 2.26 3.245(12) 170.2 . yes
C2 H2B O3A^a 0.99 2.30 3.270(9) 165.9 2_655 yes
C2 H2B O2C^c 0.99 2.55 3.524(8) 166.7 2_655 yes
C3 H3A O8C^c 0.99 2.59 3.494(7) 151.0 . yes
C4 H4A Cl1B^b 0.99 2.90 3.568(6) 125.3 4_566 yes
C4 H4A O4C^c 0.99 2.51 3.28(3) 134.1 4_566 yes
C4 H4B O1M 0.99 2.53 3.267(4) 131.2 3_656 yes
C6 H6B O1M 0.99 2.50 3.331(4) 141.7 3_656 yes
C7 H7A O9A^a 0.99 2.63 3.52(3) 150.0 3_656 yes
C7 H7A O7B^b 0.99 2.51 3.20(4) 126.6 3_656 yes
C7 H7A O7C^c 0.99 2.61 3.56(5) 161.4 3_656 yes
C7 H7A O9C^c 0.99 2.65 3.21(4) 115.7 3_656 yes
C9 H9A O7A^a 0.99 2.42 3.341(8) 155.1 . yes
C9 H9A O9B^b 0.99 2.44 3.405(14) 166.0 . yes
C9 H9A O6C^c 0.99 2.48 3.354(14) 147.7 . yes
C9 H9A O8C^c 0.99 2.64 3.575(15) 158.4 . yes
C9 H9A O6D^d 0.99 2.57 3.509(17) 158.3 . yes
C9 H9B O1M 0.99 2.48 3.270(5) 136.6 3_756 yes
C10 H10B Cl1B^b 0.99 2.69 3.640(6) 162.1 4_666 yes
C10 H10B O4B^b 0.99 1.54 2.38(9) 140.2 4_666 yes
C10 H10B O4C^c 0.99 2.49 3.38(3) 150.4 4_666 yes
C11 H11A O3A^a 0.99 2.47 3.39(4) 155.7 2_655 yes
C11 H11A O2C^c 0.99 2.62 3.54(3) 154.6 2_655 yes
C11 H11A O4D^d 0.99 2.62 3.53(5) 152.2 2_655 yes
C11 H11B O4B^b 0.99 2.54 3.12(3) 117.0 4_666 yes
C14 H14B O7A^a 0.98 2.37 3.29(4) 155.9 4_565 yes
C14 H14B O6C^c 0.98 2.53 3.34(9) 139.5 4_565 yes
C14 H14B O6D^d 0.98 2.63 3.58(7) 163.9 4_565 yes
C14 H14C O4A^a 0.98 2.17 3.129(8) 165.9 . yes
C14 H14C O5B^b 0.98 1.64 2.459(9) 137.8 . yes
C14 H14C O3D^d 0.98 2.56 3.438(10) 148.9 . yes
C15 H15B O9A^a 0.99 2.60 3.45(2) 144.7 4_565 yes
C15 H15B O8B^b 0.99 2.53 3.43(5) 149.7 4_565 yes
C15 H15B O9D^d 0.99 2.58 3.45(5) 146.3 4_565 yes
C18 H18A O8B^b 0.99 2.65 3.52(9) 147.3 4_565 yes
C18 H18A O6D^d 0.99 2.61 3.25(9) 122.2 4_565 yes
C18 H18B O2A^a 0.99 2.68 3.623(7) 159.8 . yes
C18 H18B O5C^c 0.99 2.31 3.252(4) 157.8 . yes
C18 H18B O5D^d 0.99 2.39 3.304(7) 154.1 . yes
C21 H21A O2A^a 0.99 2.55 3.460(8) 153.2 . yes
C21 H21A O5C^c 0.99 2.36 3.301(7) 157.7 . yes
C21 H21A O5D^d 0.99 2.53 3.467(11) 157.8 . yes
O1M H1M O6A^a 0.84 2.16 2.866(5) 142.0 . yes
O1M H1M O6B^b 0.84 2.08 2.909(12) 169.8 . yes
O1M H1M O9C^c 0.84 2.45 3.043(13) 127.9 . yes
O1M H1M O8D^d 0.84 1.97 2.780(8) 160.6 . yes
C1M H1M1 Cl1B^b 0.98 2.57 3.526(7) 165.9 2_645 yes
C1M H1M1 O5B^b 0.98 1.84 2.76(3) 156.0 2_645 yes
C1M H1M1 O3D^d 0.98 2.29 3.27(3) 178.3 2_645 yes
C1M H1M3 O7D^d 0.98 2.54 3.37(4) 142.4 3_656 yes

_refine_diff_density_max         1.778
_refine_diff_density_min         -1.504
_refine_diff_density_rms         0.129

####################################################################### 
# 
# 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_pjr14ajc_s001
_database_code_depnum_ccdc_archive 'CCDC 2012631'
loop_
_audit_author_name
_audit_author_address
'Peter Turner'
;University of Sydney
Australia
;
_audit_update_record             
;
2020-06-28 deposited with the CCDC.	2021-02-26 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         'C22 H32 Cu N4, 2(Cl O4)'
_chemical_formula_sum            'C22 H32 Cl2 Cu N4 O8'
_chemical_formula_weight         614.95

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.7622(2)
_cell_length_b                   15.2121(2)
_cell_length_c                   9.2034(2)
_cell_angle_alpha                90
_cell_angle_beta                 112.388(2)
_cell_angle_gamma                90
_cell_volume                     1263.72(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10877
_cell_measurement_temperature    150.0(5)
_cell_measurement_theta_max      75.6970
_cell_measurement_theta_min      4.8960

_exptl_crystal_description       prism
_exptl_crystal_colour            'translucent red'
_exptl_crystal_size_max          0.2695
_exptl_crystal_size_mid          0.1648
_exptl_crystal_size_min          0.1004
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             638
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    3.652
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.704
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
 Version 1.171.37.33 (compiled Mar 27 2014,17:12:48)
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_crystal_treatment        
;
attached with Exxon Paratone N, to a short length 
of fibre supported on a thin piece of copper wire 
inserted in a copper mounting pin.  The crystal was 
quenched in a cold nitrogen gas stream from an 
Oxford Cryosystems Cryostream. 
;

_diffrn_ambient_temperature      150.0(5)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_device       'κ-geometry four circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.5861
_diffrn_reflns_number            21129
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.899
_diffrn_reflns_theta_max         75.868
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2600
_reflns_number_gt                2359
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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_cell_refinement       
;
 CrysAlisPro, Agilent Technologies, Version 1.171.37.33 
 (compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
 CrysAlisPro, Agilent Technologies, Version 1.171.37.33 
 (compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
 CrysAlisPro, Agilent Technologies, Version 1.171.37.33 
 (compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics    
;
  OLEX2 (Dolomanov,O.V.et al., 2009)
  shelXle (Hübschle,C.B., et al., 2011) 
;

_computing_publication_material  
;    
  WinGX (Farrugia, 1999)
;

_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)+(0.03P)²+0.8P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2600
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0844
_refine_ls_wR_factor_gt          0.0823
_refine_ls_goodness_of_fit_ref   1.358
_refine_ls_restrained_S_all      1.358
_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 0.500000 0.500000 0.500000 0.01462(12) Uani 1 2 d S . P . .
N1 N 0.35002(18) 0.42179(10) 0.55919(18) 0.0172(3) Uani 1 1 d . . . . .
N2 N 0.37463(18) 0.60998(10) 0.46949(18) 0.0170(3) Uani 1 1 d . . . . .
C1 C 0.1963(2) 0.43540(13) 0.4400(2) 0.0205(4) Uani 1 1 d . . . . .
H1A H 0.129953 0.394869 0.462083 0.025 Uiso 1 1 calc R U . . .
H1B H 0.195072 0.421136 0.336791 0.025 Uiso 1 1 calc R U . . .
C2 C 0.1378(2) 0.52815(14) 0.4361(2) 0.0221(4) Uani 1 1 d . . . . .
H2A H 0.032776 0.528289 0.371488 0.027 Uiso 1 1 calc R U . . .
H2B H 0.148646 0.544358 0.541887 0.027 Uiso 1 1 calc R U . . .
C3 C 0.2128(2) 0.59766(14) 0.3741(2) 0.0219(4) Uani 1 1 d . . . . .
H3A H 0.200545 0.582086 0.267707 0.026 Uiso 1 1 calc R U . . .
H3B H 0.162659 0.653293 0.369370 0.026 Uiso 1 1 calc R U . . .
C4 C 0.4344(2) 0.67311(13) 0.3839(2) 0.0207(4) Uani 1 1 d . . . . .
H4A H 0.400459 0.732142 0.392021 0.025 Uiso 1 1 calc R U . . .
H4B H 0.399312 0.657403 0.273523 0.025 Uiso 1 1 calc R U . . .
C5 C 0.6017(2) 0.66998(12) 0.4553(2) 0.0204(4) Uani 1 1 d . . . . .
H5A H 0.642342 0.710513 0.400812 0.024 Uiso 1 1 calc R U . . .
H5B H 0.637098 0.686978 0.565068 0.024 Uiso 1 1 calc R U . . .
C6 C 0.3522(2) 0.43277(13) 0.7229(2) 0.0202(4) Uani 1 1 d . . . . .
H6A H 0.451830 0.422275 0.798547 0.024 Uiso 1 1 calc R U . . .
H6B H 0.325746 0.492849 0.736207 0.024 Uiso 1 1 calc R U . . .
C7 C 0.2490(2) 0.37223(14) 0.7551(2) 0.0236(4) Uani 1 1 d . . . . .
C8 C 0.1644(3) 0.32387(16) 0.7778(3) 0.0317(5) Uani 1 1 d . . . . .
H8 H 0.097877 0.285833 0.795677 0.038 Uiso 1 1 calc R U . . .
C9 C 0.3994(2) 0.64722(13) 0.6294(2) 0.0218(4) Uani 1 1 d . . . . .
H9A H 0.406878 0.710723 0.626451 0.026 Uiso 1 1 calc R U . . .
H9B H 0.315272 0.633026 0.656702 0.026 Uiso 1 1 calc R U . . .
C10 C 0.5349(2) 0.61167(13) 0.7496(2) 0.0229(4) Uani 1 1 d . . . . .
C11 C 0.6430(3) 0.58075(15) 0.8458(2) 0.0286(5) Uani 1 1 d . . . . .
H11 H 0.727796 0.556509 0.921200 0.034 Uiso 1 1 calc R U . . .
Cl1 Cl 0.16173(6) 0.63159(3) 0.91362(5) 0.02303(13) Uani 1 1 d . . . . .
O1 O 0.0957(2) 0.54963(13) 0.9203(3) 0.0542(6) Uani 1 1 d . . . . .
O2 O 0.1277(3) 0.69574(14) 1.0069(2) 0.0615(6) Uani 1 1 d . . . . .
O3 O 0.1146(2) 0.66380(13) 0.75564(18) 0.0392(4) Uani 1 1 d . . . . .
O4 O 0.3210(2) 0.62163(14) 0.9770(2) 0.0516(5) 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 2.0283(15) . ?
Cu1 N2 2.0283(15) 3_666 ?
Cu1 N1 2.1127(16) . ?
Cu1 N1 2.1127(16) 3_666 ?
N1 C5 1.496(2) 3_666 ?
N1 C1 1.498(2) . ?
N1 C6 1.508(2) . ?
N2 C4 1.495(2) . ?
N2 C3 1.499(2) . ?
N2 C9 1.508(2) . ?
C1 C2 1.517(3) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.516(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.511(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.476(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.182(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.467(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.186(3) . ?
C11 H11 0.9300 . ?
Cl1 O1 1.4158(19) . ?
Cl1 O2 1.420(2) . ?
Cl1 O3 1.4339(16) . ?
Cl1 O4 1.446(2) . ?

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 N2 180.0 . 3_666 ?
N2 Cu1 N1 93.40(6) . . ?
N2 Cu1 N1 86.60(6) 3_666 . ?
N2 Cu1 N1 86.60(6) . 3_666 ?
N2 Cu1 N1 93.40(6) 3_666 3_666 ?
N1 Cu1 N1 180.0 . 3_666 ?
C5 N1 C1 109.01(15) 3_666 . ?
C5 N1 C6 107.92(15) 3_666 . ?
C1 N1 C6 110.19(15) . . ?
C5 N1 Cu1 103.27(11) 3_666 . ?
C1 N1 Cu1 109.43(11) . . ?
C6 N1 Cu1 116.61(11) . . ?
C4 N2 C3 107.95(15) . . ?
C4 N2 C9 108.88(15) . . ?
C3 N2 C9 111.08(15) . . ?
C4 N2 Cu1 105.47(12) . . ?
C3 N2 Cu1 115.09(12) . . ?
C9 N2 Cu1 108.10(11) . . ?
N1 C1 C2 114.11(16) . . ?
N1 C1 H1A 108.7 . . ?
C2 C1 H1A 108.7 . . ?
N1 C1 H1B 108.7 . . ?
C2 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
C3 C2 C1 115.25(17) . . ?
C3 C2 H2A 108.5 . . ?
C1 C2 H2A 108.5 . . ?
C3 C2 H2B 108.5 . . ?
C1 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
N2 C3 C2 114.79(16) . . ?
N2 C3 H3A 108.6 . . ?
C2 C3 H3A 108.6 . . ?
N2 C3 H3B 108.6 . . ?
C2 C3 H3B 108.6 . . ?
H3A C3 H3B 107.5 . . ?
N2 C4 C5 108.95(15) . . ?
N2 C4 H4A 109.9 . . ?
C5 C4 H4A 109.9 . . ?
N2 C4 H4B 109.9 . . ?
C5 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
N1 C5 C4 108.41(15) 3_666 . ?
N1 C5 H5A 110.0 3_666 . ?
C4 C5 H5A 110.0 . . ?
N1 C5 H5B 110.0 3_666 . ?
C4 C5 H5B 110.0 . . ?
H5A C5 H5B 108.4 . . ?
C7 C6 N1 112.38(16) . . ?
C7 C6 H6A 109.1 . . ?
N1 C6 H6A 109.1 . . ?
C7 C6 H6B 109.1 . . ?
N1 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
C8 C7 C6 178.7(2) . . ?
C7 C8 H8 180.0 . . ?
C10 C9 N2 111.13(16) . . ?
C10 C9 H9A 109.4 . . ?
N2 C9 H9A 109.4 . . ?
C10 C9 H9B 109.4 . . ?
N2 C9 H9B 109.4 . . ?
H9A C9 H9B 108.0 . . ?
C11 C10 C9 178.3(2) . . ?
C10 C11 H11 180.0 . . ?
O1 Cl1 O2 111.32(15) . . ?
O1 Cl1 O3 111.68(12) . . ?
O2 Cl1 O3 108.63(12) . . ?
O1 Cl1 O4 109.13(13) . . ?
O2 Cl1 O4 106.96(15) . . ?
O3 Cl1 O4 108.99(11) . . ?

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 -176.50(16) 3_666 . . . ?
C6 N1 C1 C2 65.3(2) . . . . ?
Cu1 N1 C1 C2 -64.22(18) . . . . ?
N1 C1 C2 C3 69.1(2) . . . . ?
C4 N2 C3 C2 174.02(16) . . . . ?
C9 N2 C3 C2 -66.7(2) . . . . ?
Cu1 N2 C3 C2 56.6(2) . . . . ?
C1 C2 C3 N2 -62.5(2) . . . . ?
C3 N2 C4 C5 -166.39(15) . . . . ?
C9 N2 C4 C5 72.93(19) . . . . ?
Cu1 N2 C4 C5 -42.88(16) . . . . ?
N2 C4 C5 N1 59.49(19) . . . 3_666 ?
C5 N1 C6 C7 -61.6(2) 3_666 . . . ?
C1 N1 C6 C7 57.4(2) . . . . ?
Cu1 N1 C6 C7 -177.14(13) . . . . ?
C4 N2 C9 C10 -96.26(19) . . . . ?
C3 N2 C9 C10 145.00(17) . . . . ?
Cu1 N2 C9 C10 17.8(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1A O3 0.97 2.62 3.250(3) 122.9 3_566 yes
C4 H4A O4 0.97 2.57 3.526(3) 167.2 4_575 yes
C4 H4B O4 0.97 2.60 3.564(3) 175.9 1_554 yes
C6 H6A O4 0.97 2.48 3.432(3) 167.7 3_667 yes
C9 H9B O3 0.97 2.50 3.406(3) 155.6 . yes

_refine_diff_density_max         0.822
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.063

####################################################################### 
# 
# 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_s013
_database_code_depnum_ccdc_archive 'CCDC 2012628'
loop_
_audit_author_name
_audit_author_address
'Peter Turner'
;University of Sydney
Australia
;
_audit_update_record             
;
2020-06-28 deposited with the CCDC.	2021-02-26 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         ?
_chemical_formula_sum            'C20 H35 Cl2 Cu N5 O8'
_chemical_formula_weight         607.97

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14


_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   17.9502(2)
_cell_length_b                   9.1454(2)
_cell_length_c                   16.40970(10)
_cell_angle_alpha                90
_cell_angle_beta                 106.329(2)
_cell_angle_gamma                90
_cell_volume                     2585.18(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150.0(5)
_cell_measurement_reflns_used    68830
_cell_measurement_theta_max      75.895
_cell_measurement_theta_min      5.135

_exptl_crystal_colour            blue
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1268
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_shelx_estimated_absorpt_T_max   0.900
_shelx_estimated_absorpt_T_min   0.674
_exptl_absorpt_coefficient_mu    3.569
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78912
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33 (release 27-03-2014 CrysAlis171 .NET)
(compiled Mar 27 2014,17:12:48)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_crystal_treatment        
;
attached with Exxon Paratone N, to a short length 
of fibre supported on a thin piece of copper wire 
inserted in a copper mounting pin.  The crystal was 
quenched in a cold nitrogen gas stream from an 
Oxford Cryosystems Cryostream. 
;

_diffrn_ambient_temperature      150.0(5)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_device       'κ-geometry four circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.5861
_diffrn_reflns_number            66254
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         5.135
_diffrn_reflns_theta_max         75.895
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5401
_reflns_number_gt                4927
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       
;
  CrysAlisPro, Agilent Technologies,
;
_computing_cell_refinement       
;
  CrysAlisPro, Agilent Technologies,
;
_computing_data_reduction        
;
  CrysAlisPro, Agilent Technologies,
;
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
  OLEX2 (Dolomanov,O.V.et al., 2009)
  shelXle (Hübschle,C.B., et al., 2011) 
;

_computing_publication_material  
;    
  WinGX (Farrugia, 1999)
;


_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)+(0.045P)²+7.0P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5401
_refine_ls_number_parameters     328
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0633
_refine_ls_R_factor_gt           0.0592
_refine_ls_wR_factor_ref         0.1397
_refine_ls_wR_factor_gt          0.1375
_refine_ls_goodness_of_fit_ref   1.195
_refine_ls_restrained_S_all      1.195
_refine_ls_shift/su_max          0.003
_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 0.23728(2) 0.64004(5) 0.21927(3) 0.01756(13) Uani 1 1 d . . . . .
N1 N 0.28232(17) 0.8018(3) 0.31330(18) 0.0303(6) Uani 1 1 d . . . . .
N2 N 0.15727(17) 0.7978(3) 0.16014(18) 0.0292(6) Uani 1 1 d . . . . .
N3 N 0.18517(16) 0.4751(3) 0.13182(18) 0.0279(6) Uani 1 1 d . . . . .
N4 N 0.27838(16) 0.4694(3) 0.30387(18) 0.0269(6) Uani 1 1 d . . . . .
C1 C 0.2375(3) 0.9402(5) 0.2764(3) 0.0650(15) Uani 1 1 d . . . . .
H1A H 0.237143 1.008226 0.323270 0.078 Uiso 1 1 calc R U . . .
H1B H 0.264203 0.989502 0.238821 0.078 Uiso 1 1 calc R U . . .
C2 C 0.1587(3) 0.9077(5) 0.2289(3) 0.0563(13) Uani 1 1 d . . . . .
H2A H 0.132419 0.998562 0.203131 0.068 Uiso 1 1 calc R U . . .
H2B H 0.130132 0.868117 0.267619 0.068 Uiso 1 1 calc R U . . .
C3 C 0.0757(2) 0.7450(5) 0.1357(3) 0.0415(9) Uani 1 1 d . . . . .
H3A H 0.041755 0.825448 0.106336 0.050 Uiso 1 1 calc R U . . .
H3B H 0.061078 0.722638 0.188216 0.050 Uiso 1 1 calc R U . . .
C4 C 0.0597(2) 0.6129(5) 0.0797(2) 0.0381(9) Uani 1 1 d . . . . .
H4A H 0.076183 0.633530 0.028165 0.046 Uiso 1 1 calc R U . . .
H4B H 0.002962 0.595556 0.061494 0.046 Uiso 1 1 calc R U . . .
C5 C 0.0997(2) 0.4743(4) 0.1205(2) 0.0347(8) Uani 1 1 d . . . . .
H5A H 0.090184 0.461629 0.176686 0.042 Uiso 1 1 calc R U . . .
H5B H 0.076435 0.389544 0.084836 0.042 Uiso 1 1 calc R U . . .
C6 C 0.2171(3) 0.3315(4) 0.1751(3) 0.0447(10) Uani 1 1 d . . . . .
H6A H 0.181222 0.250426 0.150761 0.054 Uiso 1 1 calc R U . . .
H6B H 0.268099 0.310096 0.165583 0.054 Uiso 1 1 calc R U . . .
C7 C 0.2260(3) 0.3445(4) 0.2693(3) 0.0462(10) Uani 1 1 d . . . . .
H7A H 0.174615 0.360833 0.278958 0.055 Uiso 1 1 calc R U . . .
H7B H 0.248055 0.252969 0.298460 0.055 Uiso 1 1 calc R U . . .
C8 C 0.2708(3) 0.4925(5) 0.3913(2) 0.0432(9) Uani 1 1 d . . . . .
H8A H 0.214862 0.493213 0.388151 0.052 Uiso 1 1 calc R U . . .
H8B H 0.294635 0.408142 0.426959 0.052 Uiso 1 1 calc R U . . .
C9 C 0.3067(3) 0.6294(5) 0.4344(3) 0.0470(10) Uani 1 1 d . . . . .
H9A H 0.361636 0.633524 0.433703 0.056 Uiso 1 1 calc R U . . .
H9B H 0.305932 0.626712 0.494476 0.056 Uiso 1 1 calc R U . . .
C10 C 0.2661(3) 0.7644(5) 0.3936(3) 0.0451(10) Uani 1 1 d . . . . .
H10A H 0.209433 0.750790 0.382849 0.054 Uiso 1 1 calc R U . . .
H10B H 0.281942 0.847341 0.433496 0.054 Uiso 1 1 calc R U . . .
C11 C 0.3640(3) 0.8470(5) 0.3267(3) 0.0439(10) Uani 1 1 d . . . . .
H11A H 0.398376 0.760968 0.343565 0.053 Uiso 1 1 calc R U . . .
H11B H 0.370815 0.885562 0.272843 0.053 Uiso 1 1 calc R U . . .
C12 C 0.3864(3) 0.9605(5) 0.3932(3) 0.0519(12) Uani 1 1 d . . . . .
C13 C 0.4013(3) 1.0495(6) 0.4474(3) 0.0578(13) Uani 1 1 d . . . . .
H13 H 0.413240 1.121170 0.491093 0.069 Uiso 1 1 calc R U . . .
C14 C 0.1742(2) 0.8690(5) 0.0863(3) 0.0442(10) Uani 1 1 d . . . . .
H14A H 0.170591 0.796543 0.041378 0.066 Uiso 1 1 calc R U . . .
H14B H 0.226712 0.910183 0.103683 0.066 Uiso 1 1 calc R U . . .
H14C H 0.136527 0.947368 0.065056 0.066 Uiso 1 1 calc R U . . .
C16 C 0.1675(3) 0.3602(5) -0.0086(3) 0.0490(11) Uani 1 1 d . . . . .
C15 C 0.2044(2) 0.4787(5) 0.0496(2) 0.0407(9) Uani 1 1 d . . . . .
H15A H 0.187855 0.573850 0.021691 0.049 Uiso 1 1 calc R U . . .
H15B H 0.261456 0.471465 0.060779 0.049 Uiso 1 1 calc R U . . .
C17 C 0.1360(3) 0.2666(7) -0.0551(3) 0.0683(17) Uani 1 1 d . . . . .
H17 H 0.110707 0.191163 -0.092570 0.082 Uiso 1 1 calc R U . . .
C18 C 0.3593(2) 0.4317(5) 0.3095(3) 0.0486(11) Uani 1 1 d . . . . .
H18A H 0.374835 0.345591 0.345889 0.073 Uiso 1 1 calc R U . . .
H18B H 0.393133 0.514180 0.333802 0.073 Uiso 1 1 calc R U . . .
H18C H 0.363914 0.410195 0.252624 0.073 Uiso 1 1 calc R U . . .
N1S N 0.33341(16) 0.6752(3) 0.16003(18) 0.0286(6) Uani 1 1 d . . . . .
C1S C 0.38927(19) 0.6979(4) 0.1434(2) 0.0294(7) Uani 1 1 d . . . . .
C2S C 0.4615(2) 0.7286(6) 0.1228(3) 0.0524(12) Uani 1 1 d . . . . .
H2SA H 0.459930 0.828253 0.100395 0.079 Uiso 1 1 calc R U . . .
H2SB H 0.467925 0.658830 0.079943 0.079 Uiso 1 1 calc R U . . .
H2SC H 0.505150 0.719413 0.174119 0.079 Uiso 1 1 calc R U . . .
Cl1 Cl 0.02675(4) 0.66081(9) 0.35262(5) 0.02818(19) Uani 1 1 d . . . . .
O1 O 0.0786(2) 0.5554(4) 0.3346(2) 0.0626(9) Uani 1 1 d . . . . .
O2 O -0.03525(16) 0.6895(4) 0.27772(18) 0.0451(7) Uani 1 1 d . . . . .
O3 O -0.00481(18) 0.6096(4) 0.41826(18) 0.0477(7) Uani 1 1 d . . . . .
O4 O 0.06846(17) 0.7950(3) 0.37986(18) 0.0436(7) Uani 1 1 d . . . . .
Cl2 Cl 0.41863(5) 0.14967(11) 0.12670(6) 0.0368(2) Uani 1 1 d . . . . .
O5 O 0.4732(4) 0.0927(9) 0.1980(3) 0.150(3) Uani 1 1 d . . . . .
O6 O 0.4458(3) 0.1169(5) 0.0551(2) 0.0732(11) Uani 1 1 d . . . . .
O7 O 0.3480(3) 0.0819(7) 0.1210(4) 0.115(2) Uani 1 1 d . . . . .
O8 O 0.4143(4) 0.3000(5) 0.1378(4) 0.125(3) 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 2.074(3) . ?
Cu1 N4 2.081(3) . ?
Cu1 N3 2.111(3) . ?
Cu1 N1 2.126(3) . ?
Cu1 N1S 2.229(3) . ?
Cu1 O1 3.914(4) . ?
N1 C10 1.467(5) . ?
N1 C11 1.480(5) . ?
N1 C1 1.530(5) . ?
N2 C14 1.480(5) . ?
N2 C3 1.486(5) . ?
N2 C2 1.506(5) . ?
N3 C15 1.484(4) . ?
N3 C5 1.493(4) . ?
N3 C6 1.526(5) . ?
N4 C18 1.470(5) . ?
N4 C7 1.487(5) . ?
N4 C8 1.494(5) . ?
C1 C2 1.442(7) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.496(6) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.516(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.513(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.493(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.494(7) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.478(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.180(6) . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C16 C17 1.180(7) . ?
C16 C15 1.474(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C17 H17 0.9500 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
N1S C1S 1.130(4) . ?
C1S C2S 1.456(5) . ?
C2S H2SA 0.9800 . ?
C2S H2SB 0.9800 . ?
C2S H2SC 0.9800 . ?
Cl1 O1 1.428(3) . ?
Cl1 O3 1.430(3) . ?
Cl1 O2 1.431(3) . ?
Cl1 O4 1.442(3) . ?
Cl2 O7 1.390(4) . ?
Cl2 O8 1.392(4) . ?
Cl2 O5 1.398(5) . ?
Cl2 O6 1.425(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 N4 154.50(12) . . ?
N2 Cu1 N3 93.61(11) . . ?
N4 Cu1 N3 85.63(12) . . ?
N2 Cu1 N1 85.84(12) . . ?
N4 Cu1 N1 92.67(12) . . ?
N3 Cu1 N1 174.86(12) . . ?
N2 Cu1 N1S 102.40(12) . . ?
N4 Cu1 N1S 103.09(11) . . ?
N3 Cu1 N1S 93.21(11) . . ?
N1 Cu1 N1S 91.90(11) . . ?
N2 Cu1 O1 82.04(10) . . ?
N4 Cu1 O1 72.47(9) . . ?
N3 Cu1 O1 86.77(9) . . ?
N1 Cu1 O1 88.09(10) . . ?
N1S Cu1 O1 175.55(9) . . ?
C10 N1 C11 111.8(3) . . ?
C10 N1 C1 109.4(4) . . ?
C11 N1 C1 102.5(4) . . ?
C10 N1 Cu1 111.0(2) . . ?
C11 N1 Cu1 117.4(2) . . ?
C1 N1 Cu1 103.8(2) . . ?
C14 N2 C3 109.6(3) . . ?
C14 N2 C2 110.8(3) . . ?
C3 N2 C2 103.1(3) . . ?
C14 N2 Cu1 114.5(2) . . ?
C3 N2 Cu1 113.6(2) . . ?
C2 N2 Cu1 104.5(2) . . ?
C15 N3 C5 112.4(3) . . ?
C15 N3 C6 106.8(3) . . ?
C5 N3 C6 107.0(3) . . ?
C15 N3 Cu1 115.5(2) . . ?
C5 N3 Cu1 109.4(2) . . ?
C6 N3 Cu1 105.2(2) . . ?
C18 N4 C7 110.6(3) . . ?
C18 N4 C8 109.2(3) . . ?
C7 N4 C8 104.9(3) . . ?
C18 N4 Cu1 112.1(2) . . ?
C7 N4 Cu1 104.7(2) . . ?
C8 N4 Cu1 115.0(2) . . ?
C2 C1 N1 111.7(4) . . ?
C2 C1 H1A 109.3 . . ?
N1 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
N1 C1 H1B 109.3 . . ?
H1A C1 H1B 107.9 . . ?
C1 C2 N2 110.5(4) . . ?
C1 C2 H2A 109.5 . . ?
N2 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
N2 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
N2 C3 C4 115.7(3) . . ?
N2 C3 H3A 108.4 . . ?
C4 C3 H3A 108.4 . . ?
N2 C3 H3B 108.4 . . ?
C4 C3 H3B 108.4 . . ?
H3A C3 H3B 107.4 . . ?
C3 C4 C5 114.7(3) . . ?
C3 C4 H4A 108.6 . . ?
C5 C4 H4A 108.6 . . ?
C3 C4 H4B 108.6 . . ?
C5 C4 H4B 108.6 . . ?
H4A C4 H4B 107.6 . . ?
N3 C5 C4 113.1(3) . . ?
N3 C5 H5A 109.0 . . ?
C4 C5 H5A 109.0 . . ?
N3 C5 H5B 109.0 . . ?
C4 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C7 C6 N3 109.0(3) . . ?
C7 C6 H6A 109.9 . . ?
N3 C6 H6A 109.9 . . ?
C7 C6 H6B 109.9 . . ?
N3 C6 H6B 109.9 . . ?
H6A C6 H6B 108.3 . . ?
N4 C7 C6 108.9(3) . . ?
N4 C7 H7A 109.9 . . ?
C6 C7 H7A 109.9 . . ?
N4 C7 H7B 109.9 . . ?
C6 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
C9 C8 N4 115.4(3) . . ?
C9 C8 H8A 108.4 . . ?
N4 C8 H8A 108.4 . . ?
C9 C8 H8B 108.4 . . ?
N4 C8 H8B 108.4 . . ?
H8A C8 H8B 107.5 . . ?
C8 C9 C10 112.9(4) . . ?
C8 C9 H9A 109.0 . . ?
C10 C9 H9A 109.0 . . ?
C8 C9 H9B 109.0 . . ?
C10 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?
N1 C10 C9 113.6(3) . . ?
N1 C10 H10A 108.8 . . ?
C9 C10 H10A 108.8 . . ?
N1 C10 H10B 108.8 . . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C12 C11 N1 111.0(4) . . ?
C12 C11 H11A 109.4 . . ?
N1 C11 H11A 109.4 . . ?
C12 C11 H11B 109.4 . . ?
N1 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C13 C12 C11 176.9(5) . . ?
C12 C13 H13 180.0 . . ?
N2 C14 H14A 109.5 . . ?
N2 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N2 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C17 C16 C15 178.2(5) . . ?
C16 C15 N3 113.4(3) . . ?
C16 C15 H15A 108.9 . . ?
N3 C15 H15A 108.9 . . ?
C16 C15 H15B 108.9 . . ?
N3 C15 H15B 108.9 . . ?
H15A C15 H15B 107.7 . . ?
C16 C17 H17 180.0 . . ?
N4 C18 H18A 109.5 . . ?
N4 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N4 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C1S N1S Cu1 168.6(3) . . ?
N1S C1S C2S 179.2(4) . . ?
C1S C2S H2SA 109.5 . . ?
C1S C2S H2SB 109.5 . . ?
H2SA C2S H2SB 109.5 . . ?
C1S C2S H2SC 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 109.5 . . ?
O1 Cl1 O3 110.8(2) . . ?
O1 Cl1 O2 109.9(2) . . ?
O3 Cl1 O2 109.26(18) . . ?
O1 Cl1 O4 109.1(2) . . ?
O3 Cl1 O4 109.06(17) . . ?
O2 Cl1 O4 108.70(19) . . ?
Cl1 O1 Cu1 124.9(2) . . ?
O7 Cl2 O8 111.5(4) . . ?
O7 Cl2 O5 107.6(5) . . ?
O8 Cl2 O5 108.1(4) . . ?
O7 Cl2 O6 111.5(3) . . ?
O8 Cl2 O6 111.1(3) . . ?
O5 Cl2 O6 106.8(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
C10 N1 C1 C2 -83.6(5) . . . . ?
C11 N1 C1 C2 157.7(4) . . . . ?
Cu1 N1 C1 C2 35.0(5) . . . . ?
N1 C1 C2 N2 -55.8(6) . . . . ?
C14 N2 C2 C1 -78.9(5) . . . . ?
C3 N2 C2 C1 163.9(4) . . . . ?
Cu1 N2 C2 C1 44.9(5) . . . . ?
C14 N2 C3 C4 73.3(4) . . . . ?
C2 N2 C3 C4 -168.7(3) . . . . ?
Cu1 N2 C3 C4 -56.2(4) . . . . ?
N2 C3 C4 C5 65.7(4) . . . . ?
C15 N3 C5 C4 -64.4(4) . . . . ?
C6 N3 C5 C4 178.7(3) . . . . ?
Cu1 N3 C5 C4 65.2(3) . . . . ?
C3 C4 C5 N3 -72.0(4) . . . . ?
C15 N3 C6 C7 159.5(3) . . . . ?
C5 N3 C6 C7 -79.9(4) . . . . ?
Cu1 N3 C6 C7 36.4(4) . . . . ?
C18 N4 C7 C6 -73.6(4) . . . . ?
C8 N4 C7 C6 168.8(3) . . . . ?
Cu1 N4 C7 C6 47.3(4) . . . . ?
N3 C6 C7 N4 -58.0(4) . . . . ?
C18 N4 C8 C9 72.1(4) . . . . ?
C7 N4 C8 C9 -169.4(4) . . . . ?
Cu1 N4 C8 C9 -54.9(4) . . . . ?
N4 C8 C9 C10 67.7(5) . . . . ?
C11 N1 C10 C9 -67.7(4) . . . . ?
C1 N1 C10 C9 179.4(4) . . . . ?
Cu1 N1 C10 C9 65.5(4) . . . . ?
C8 C9 C10 N1 -75.1(5) . . . . ?
C10 N1 C11 C12 -50.5(5) . . . . ?
C1 N1 C11 C12 66.5(4) . . . . ?
Cu1 N1 C11 C12 179.5(3) . . . . ?
C5 N3 C15 C16 -54.4(5) . . . . ?
C6 N3 C15 C16 62.7(4) . . . . ?
Cu1 N3 C15 C16 179.2(3) . . . . ?
O3 Cl1 O1 Cu1 -160.41(17) . . . . ?
O2 Cl1 O1 Cu1 78.7(2) . . . . ?
O4 Cl1 O1 Cu1 -40.4(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2 H2A O2 0.99 2.55 3.381(5) 141.5 2 yes
C2 H2B O4 0.99 2.49 3.475(6) 171.8 . yes
C2S H2SC O5 0.98 2.33 3.104(7) 135.0 2_655 yes
C3 H3B Cl1 0.99 2.99 3.974(4) 176.5 . yes
C3 H3B O2 0.99 2.58 3.502(5) 154.6 . yes
C4 H4A O4 0.99 2.49 3.432(5) 159.9 4_575 yes
C8 H8A O1 0.99 2.42 3.359(6) 157.7 . yes
C10 H10A O4 0.99 2.55 3.502(5) 161.4 . yes
C14 H14B O7 0.98 2.63 3.585(6) 163.5 1_565 yes
C15 H15B N1S 0.99 2.57 3.084(5) 112.2 . yes
C18 H18C O8 0.98 2.52 3.454(7) 159.6 . yes

_refine_diff_density_max         1.398
_refine_diff_density_min         -0.836
_refine_diff_density_rms         0.095

####################################################################### 
# 
# 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_140506b
_database_code_depnum_ccdc_archive 'CCDC 2012632'
loop_
_audit_author_name
_audit_author_address
'Peter Turner'
;University of Sydney
Australia
;
_audit_update_record             
;
2020-06-28 deposited with the CCDC.	2021-02-26 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         ?
_chemical_formula_sum            'C22 H33.33 Cl2 Cu N4 O8.67'
_chemical_formula_weight         626.96

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2

_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, -z'

_cell_length_a                   8.4532(2)
_cell_length_b                   16.0765(4)
_cell_length_c                   16.5437(4)
_cell_angle_alpha                62.155(3)
_cell_angle_beta                 85.199(2)
_cell_angle_gamma                82.390(2)
_cell_volume                     1969.82(10)
_cell_formula_units_Z            3
_cell_measurement_reflns_used    21323
_cell_measurement_temperature    150.0(5)
_cell_measurement_theta_max      75.5550
_cell_measurement_theta_min      3.0060

_exptl_crystal_description       block
_exptl_crystal_colour            violet
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_F_000             977
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    3.545
_shelx_estimated_absorpt_T_max   0.932
_shelx_estimated_absorpt_T_min   0.676
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50477
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
 Version 1.171.37.31d (compiled Feb 11 2014,18:09:27)
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_crystal_treatment        
;
attached with Exxon Paratone N, to a short length 
of fibre supported on a thin piece of copper wire 
inserted in a copper mounting pin.  The crystal was 
quenched in a cold nitrogen gas stream from an 
Oxford Cryosystems Cryostream. 
;

_diffrn_ambient_temperature      150.0(5)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_device       'κ-geometry four circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.5861
_diffrn_measurement_method       ω
_diffrn_reflns_number            70340
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_av_R_equivalents  0.0555
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.022
_diffrn_reflns_theta_max         72.118
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7779
_reflns_number_gt                7058
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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_cell_refinement       
;
 CrysAlisPro, Agilent Technologies, Version 1.171.37.33 
 (compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
 CrysAlisPro, Agilent Technologies, Version 1.171.37.33 
 (compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
 CrysAlisPro, Agilent Technologies, Version 1.171.37.33 
 (compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics    
;
  OLEX2 (Dolomanov,O.V.et al., 2009)
  shelXle (Hübschle,C.B., et al., 2011) 
;

_computing_publication_material  
;    
  WinGX (Farrugia, 1999)
;

_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)+(0.03P)²+5.0P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7779
_refine_ls_number_parameters     519
_refine_ls_number_restraints     63
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.0989
_refine_ls_wR_factor_gt          0.0958
_refine_ls_goodness_of_fit_ref   0.972
_refine_ls_restrained_S_all      0.974
_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
Cu1_1 Cu 0.25398(4) 0.15835(2) 0.68031(2) 0.02032(9) Uani 1 1 d . . . . .
N1_1 N 0.3654(3) 0.27024(15) 0.66798(14) 0.0230(4) Uani 1 1 d . . . . .
N2_1 N 0.0648(2) 0.24332(15) 0.60080(14) 0.0225(4) Uani 1 1 d . . . . .
N3_1 N 0.1674(3) 0.04822(15) 0.67263(15) 0.0244(4) Uani 1 1 d . . . . .
N4_1 N 0.4011(2) 0.07396(15) 0.78928(14) 0.0224(4) Uani 1 1 d . . . . .
C1_1 C 0.2554(3) 0.34620(19) 0.67772(19) 0.0277(6) Uani 1 1 d . . . . .
H1A_1 H 0.318916 0.397342 0.669234 0.033 Uiso 1 1 calc R U . . .
H1B_1 H 0.210373 0.319554 0.740927 0.033 Uiso 1 1 calc R U . . .
C2_1 C 0.1181(3) 0.38943(19) 0.61165(19) 0.0297(6) Uani 1 1 d . . . . .
H2A_1 H 0.060605 0.443084 0.619513 0.036 Uiso 1 1 calc R U . . .
H2B_1 H 0.162956 0.415277 0.548428 0.036 Uiso 1 1 calc R U . . .
C3_1 C -0.0017(3) 0.32188(19) 0.62276(18) 0.0264(5) Uani 1 1 d . . . . .
H3A_1 H -0.043547 0.293885 0.686653 0.032 Uiso 1 1 calc R U . . .
H3B_1 H -0.092669 0.358449 0.582512 0.032 Uiso 1 1 calc R U . . .
C4_1 C -0.0559(3) 0.17406(19) 0.62957(18) 0.0257(5) Uani 1 1 d . . . . .
H4A_1 H -0.151216 0.203730 0.591196 0.031 Uiso 1 1 calc R U . . .
H4B_1 H -0.089752 0.154845 0.694064 0.031 Uiso 1 1 calc R U . . .
C5_1 C 0.0164(3) 0.0883(2) 0.61930(19) 0.0285(6) Uani 1 1 d . . . . .
H5A_1 H -0.060075 0.040069 0.642397 0.034 Uiso 1 1 calc R U . . .
H5B_1 H 0.040459 0.106407 0.553940 0.034 Uiso 1 1 calc R U . . .
C6_1 C 0.1233(3) -0.02513(19) 0.76660(18) 0.0271(6) Uani 1 1 d . . . . .
H6A_1 H 0.076499 -0.075355 0.760834 0.033 Uiso 1 1 calc R U . . .
H6B_1 H 0.039490 0.004649 0.793246 0.033 Uiso 1 1 calc R U . . .
C7_1 C 0.2598(3) -0.07091(19) 0.83261(19) 0.0289(6) Uani 1 1 d . . . . .
H7A_1 H 0.349202 -0.093655 0.802841 0.035 Uiso 1 1 calc R U . . .
H7B_1 H 0.224018 -0.126842 0.886979 0.035 Uiso 1 1 calc R U . . .
C8_1 C 0.3217(3) -0.00649(19) 0.86438(17) 0.0261(5) Uani 1 1 d . . . . .
H8A_1 H 0.231345 0.019630 0.890730 0.031 Uiso 1 1 calc R U . . .
H8B_1 H 0.399070 -0.044607 0.913449 0.031 Uiso 1 1 calc R U . . .
C9_1 C 0.4269(3) 0.14289(19) 0.82270(18) 0.0258(5) Uani 1 1 d . . . . .
H9A_1 H 0.507119 0.114057 0.871241 0.031 Uiso 1 1 calc R U . . .
H9B_1 H 0.325764 0.160330 0.848588 0.031 Uiso 1 1 calc R U . . .
C10_1 C 0.4846(3) 0.22974(19) 0.74317(18) 0.0266(5) Uani 1 1 d . . . . .
H10A_1 H 0.497841 0.277485 0.763292 0.032 Uiso 1 1 calc R U . . .
H10B_1 H 0.589528 0.212837 0.720252 0.032 Uiso 1 1 calc R U . . .
C11_1 C 0.4534(3) 0.31084(19) 0.57731(18) 0.0264(5) Uani 1 1 d . . . . .
H11A_1 H 0.382795 0.361627 0.530477 0.032 Uiso 1 1 calc R U . . .
H11B_1 H 0.547613 0.338848 0.581857 0.032 Uiso 1 1 calc R U . . .
C12_1 C 0.5050(3) 0.2369(2) 0.54978(18) 0.0271(6) Uani 1 1 d . . . . .
C13_1 C 0.5446(3) 0.1772(2) 0.5275(2) 0.0336(6) Uani 1 1 d . . . . .
H13_1 H 0.576521 0.129224 0.509486 0.040 Uiso 1 1 calc R U . . .
C14_1 C 0.1001(3) 0.2833(2) 0.49955(17) 0.0274(6) Uani 1 1 d . . . . .
H14A_1 H 0.172520 0.333169 0.480492 0.033 Uiso 1 1 calc R U . . .
H14B_1 H 0.155080 0.232562 0.486188 0.033 Uiso 1 1 calc R U . . .
C15_1 C -0.0463(4) 0.3232(2) 0.44700(19) 0.0330(6) Uani 1 1 d . . . . .
C16_1 C -0.1711(4) 0.3520(2) 0.4116(2) 0.0454(8) Uani 1 1 d . . . . .
H16_1 H -0.271628 0.375243 0.383134 0.054 Uiso 1 1 calc R U . . .
C17_1 C 0.2820(3) 0.00612(19) 0.62386(19) 0.0271(5) Uani 1 1 d . . . . .
H17A_1 H 0.302569 0.055762 0.560990 0.032 Uiso 1 1 calc R U . . .
H17B_1 H 0.384611 -0.016414 0.655932 0.032 Uiso 1 1 calc R U . . .
C18_1 C 0.2212(3) -0.0733(2) 0.6193(2) 0.0312(6) Uani 1 1 d . . . . .
C19_1 C 0.1678(4) -0.1368(2) 0.6181(2) 0.0396(7) Uani 1 1 d . . . . .
H19_1 H 0.124869 -0.188060 0.617114 0.048 Uiso 1 1 calc R U . . .
C20_1 C 0.5579(3) 0.03433(19) 0.76430(18) 0.0266(5) Uani 1 1 d . . . . .
H20A_1 H 0.538772 -0.016997 0.750327 0.032 Uiso 1 1 calc R U . . .
H20B_1 H 0.602814 0.084688 0.708293 0.032 Uiso 1 1 calc R U . . .
C21_1 C 0.6751(3) -0.0030(2) 0.8371(2) 0.0309(6) Uani 1 1 d . . . . .
C22_1 C 0.7670(4) -0.0324(3) 0.8961(2) 0.0432(8) Uani 1 1 d . . . . .
H22_1 H 0.841374 -0.056173 0.943890 0.052 Uiso 1 1 calc R U . . .
Cu1_2 Cu 0.000000 0.500000 0.000000 0.01952(12) Uani 1 2 d S . P . .
N1_2 N 0.0828(3) 0.49241(16) 0.11506(15) 0.0264(5) Uani 1 1 d . . . . .
N2_2 N -0.2199(3) 0.57823(15) 0.00618(15) 0.0243(4) Uani 1 1 d . . . . .
C1_2 C -0.0357(4) 0.4662(2) 0.19339(18) 0.0337(6) Uani 1 1 d . . . . .
H1A_2 H 0.013474 0.467830 0.244827 0.040 Uiso 1 1 calc R U . . .
H1B_2 H -0.058287 0.400364 0.213920 0.040 Uiso 1 1 calc R U . . .
C2_2 C -0.1925(4) 0.5291(2) 0.17262(19) 0.0327(6) Uani 1 1 d . . . . .
H2A_2 H -0.257923 0.509331 0.229802 0.039 Uiso 1 1 calc R U . . .
H2B_2 H -0.170100 0.594941 0.152349 0.039 Uiso 1 1 calc R U . . .
C3_2 C -0.2891(3) 0.52763(19) 0.10048(19) 0.0296(6) Uani 1 1 d . . . . .
H3A_2 H -0.296165 0.461081 0.115019 0.035 Uiso 1 1 calc R U . . .
H3B_2 H -0.398835 0.557206 0.102355 0.035 Uiso 1 1 calc R U . . .
C4_2 C -0.3220(3) 0.5717(2) -0.0602(2) 0.0310(6) Uani 1 1 d . . . . .
H4A_2 H -0.412947 0.621834 -0.077728 0.037 Uiso 1 1 calc R U . . .
H4B_2 H -0.364950 0.509526 -0.031666 0.037 Uiso 1 1 calc R U . . .
C5_2 C 0.2211(4) 0.4166(2) 0.1436(2) 0.0327(6) Uani 1 1 d . . . . .
H5A_2 H 0.181475 0.353515 0.173314 0.039 Uiso 1 1 calc R U . . .
H5B_2 H 0.285773 0.421642 0.187987 0.039 Uiso 1 1 calc R U . . .
C6_2 C 0.1422(4) 0.5865(2) 0.0906(2) 0.0324(6) Uani 1 1 d . . . . .
H6A_2 H 0.062932 0.623314 0.112263 0.039 Uiso 1 1 calc R U . . .
H6B_2 H 0.243480 0.575214 0.121913 0.039 Uiso 1 1 calc R U . . .
C7_2 C 0.1682(3) 0.6412(2) -0.0082(2) 0.0329(6) Uani 1 1 d . . . . .
C8_2 C 0.1847(4) 0.6846(2) -0.0881(2) 0.0423(7) Uani 1 1 d . . . . .
H11C_2 H 0.198012 0.719588 -0.152554 0.051 Uiso 1 1 calc R U . . .
C9_2 C -0.2173(3) 0.68152(19) -0.02109(18) 0.0270(5) Uani 1 1 d . . . . .
H9A_2 H -0.130976 0.688672 0.011416 0.032 Uiso 1 1 calc R U . . .
H9B_2 H -0.193598 0.716178 -0.087556 0.032 Uiso 1 1 calc R U . . .
C10_2 C -0.3705(4) 0.7233(2) 0.0004(2) 0.0317(6) Uani 1 1 d . . . . .
C11_2 C -0.4943(4) 0.7514(2) 0.0231(2) 0.0380(7) Uani 1 1 d . . . . .
H11A_2 H -0.593393 0.773965 0.041363 0.046 Uiso 1 1 calc R U . . .
Cl1_3 Cl -0.04771(8) 0.18170(5) 0.88624(4) 0.02757(14) Uani 1 1 d D . . . .
O1_3 O 0.0270(3) 0.14609(15) 0.82519(14) 0.0378(5) Uani 1 1 d D . . . .
O2_3 O -0.1874(3) 0.2423(2) 0.84621(19) 0.0639(8) Uani 1 1 d D . . . .
O3_3 O -0.0824(4) 0.1052(2) 0.97167(16) 0.0623(8) Uani 1 1 d D . . . .
O4_3 O 0.0653(3) 0.23343(18) 0.89947(18) 0.0495(6) Uani 1 1 d D . . . .
Cl1_4 Cl 0.36204(8) 0.50702(4) 0.32842(4) 0.02702(14) Uani 1 1 d D . . . .
O1_4 O 0.1989(3) 0.5034(3) 0.3194(2) 0.0879(11) Uani 1 1 d D . . . .
O2_4 O 0.4288(3) 0.56664(17) 0.24244(16) 0.0506(6) Uani 1 1 d D . . . .
O3_4 O 0.3735(4) 0.5389(2) 0.39433(18) 0.0656(8) Uani 1 1 d D . . . .
O4_4 O 0.4376(5) 0.4132(2) 0.3612(2) 0.0953(13) Uani 1 1 d D . . . .
Cl1_5 Cl 0.27673(8) 0.14662(5) 0.31953(5) 0.03414(16) Uani 1 1 d D . . . .
O1_5 O 0.2468(5) 0.1947(2) 0.3717(2) 0.0842(11) Uani 1 1 d D . . . .
O2_5 O 0.2851(4) 0.04773(19) 0.3743(2) 0.0769(10) Uani 1 1 d D . . . .
O3_5 O 0.1475(4) 0.1747(3) 0.2581(2) 0.0861(11) Uani 1 1 d D . . . .
O4_5 O 0.4197(3) 0.17245(18) 0.26437(19) 0.0525(6) Uani 1 1 d D . . . .
O1W O 0.5846(3) 0.32779(19) 0.25226(19) 0.0510(6) Uani 1 1 d . . . . .
H1W H 0.533(5) 0.346(3) 0.289(3) 0.054(12) Uiso 1 1 d . . . . .
H2W H 0.541(6) 0.274(4) 0.268(3) 0.086(17) Uiso 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_1 N1_1 2.059(2) . ?
Cu1_1 N2_1 2.061(2) . ?
Cu1_1 N3_1 2.063(2) . ?
Cu1_1 N4_1 2.069(2) . ?
Cu1_1 C12_1 2.856(3) . ?
Cu1_1 O1_3 2.890(2) . ?
Cu1_1 C13_1 3.311(3) . ?
N1_1 C1_1 1.496(3) . ?
N1_1 C11_1 1.502(3) . ?
N1_1 C10_1 1.506(3) . ?
N2_1 C4_1 1.494(3) . ?
N2_1 C3_1 1.500(3) . ?
N2_1 C14_1 1.506(3) . ?
N3_1 C6_1 1.501(3) . ?
N3_1 C17_1 1.501(3) . ?
N3_1 C5_1 1.504(3) . ?
N4_1 C9_1 1.496(3) . ?
N4_1 C8_1 1.502(3) . ?
N4_1 C20_1 1.504(3) . ?
C1_1 C2_1 1.522(4) . ?
C1_1 H1A_1 0.9900 . ?
C1_1 H1B_1 0.9900 . ?
C2_1 C3_1 1.521(4) . ?
C2_1 H2A_1 0.9900 . ?
C2_1 H2B_1 0.9900 . ?
C3_1 H3A_1 0.9900 . ?
C3_1 H3B_1 0.9900 . ?
C4_1 C5_1 1.511(4) . ?
C4_1 H4A_1 0.9900 . ?
C4_1 H4B_1 0.9900 . ?
C5_1 H5A_1 0.9900 . ?
C5_1 H5B_1 0.9900 . ?
C6_1 C7_1 1.517(4) . ?
C6_1 H6A_1 0.9900 . ?
C6_1 H6B_1 0.9900 . ?
C7_1 C8_1 1.523(4) . ?
C7_1 H7A_1 0.9900 . ?
C7_1 H7B_1 0.9900 . ?
C8_1 H8A_1 0.9900 . ?
C8_1 H8B_1 0.9900 . ?
C9_1 C10_1 1.509(4) . ?
C9_1 H9A_1 0.9900 . ?
C9_1 H9B_1 0.9900 . ?
C10_1 H10A_1 0.9900 . ?
C10_1 H10B_1 0.9900 . ?
C11_1 C12_1 1.465(4) . ?
C11_1 H11A_1 0.9900 . ?
C11_1 H11B_1 0.9900 . ?
C12_1 C13_1 1.180(4) . ?
C13_1 H13_1 0.9500 . ?
C14_1 C15_1 1.465(4) . ?
C14_1 H14A_1 0.9900 . ?
C14_1 H14B_1 0.9900 . ?
C15_1 C16_1 1.179(5) . ?
C16_1 H16_1 0.9500 . ?
C17_1 C18_1 1.473(4) . ?
C17_1 H17A_1 0.9900 . ?
C17_1 H17B_1 0.9900 . ?
C18_1 C19_1 1.179(4) . ?
C19_1 H19_1 0.9500 . ?
C20_1 C21_1 1.469(4) . ?
C20_1 H20A_1 0.9900 . ?
C20_1 H20B_1 0.9900 . ?
C21_1 C22_1 1.175(4) . ?
C22_1 H22_1 0.9500 . ?
Cu1_2 N1_2 2.028(2) . ?
Cu1_2 N1_2 2.028(2) 2_565 ?
Cu1_2 N2_2 2.125(2) 2_565 ?
Cu1_2 N2_2 2.125(2) . ?
Cu1_2 C7_2 2.780(3) . ?
Cu1_2 C8_2 3.190(3) . ?
N1_2 C1_2 1.498(3) . ?
N1_2 C5_2 1.500(3) . ?
N1_2 C6_2 1.517(4) . ?
N2_2 C3_2 1.492(3) . ?
N2_2 C4_2 1.501(3) . ?
N2_2 C9_2 1.506(3) . ?
C1_2 C2_2 1.514(4) . ?
C1_2 H1A_2 0.9900 . ?
C1_2 H1B_2 0.9900 . ?
C2_2 C3_2 1.512(4) . ?
C2_2 H2A_2 0.9900 . ?
C2_2 H2B_2 0.9900 . ?
C3_2 H3A_2 0.9900 . ?
C3_2 H3B_2 0.9900 . ?
C4_2 C5_2 1.506(4) 2_565 ?
C4_2 H4A_2 0.9900 . ?
C4_2 H4B_2 0.9900 . ?
C5_2 H5A_2 0.9900 . ?
C5_2 H5B_2 0.9900 . ?
C6_2 C7_2 1.464(4) . ?
C6_2 H6A_2 0.9900 . ?
C6_2 H6B_2 0.9900 . ?
C7_2 C8_2 1.177(5) . ?
C8_2 H11C_2 0.9500 . ?
C9_2 C10_2 1.473(4) . ?
C9_2 H9A_2 0.9900 . ?
C9_2 H9B_2 0.9900 . ?
C10_2 C11_2 1.188(4) . ?
C11_2 H11A_2 0.9500 . ?
Cl1_3 O3_3 1.414(2) . ?
Cl1_3 O2_3 1.416(2) . ?
Cl1_3 O4_3 1.438(2) . ?
Cl1_3 O1_3 1.444(2) . ?
Cl1_4 O1_4 1.411(3) . ?
Cl1_4 O2_4 1.413(2) . ?
Cl1_4 O3_4 1.419(2) . ?
Cl1_4 O4_4 1.420(3) . ?
Cl1_5 O1_5 1.393(3) . ?
Cl1_5 O2_5 1.410(3) . ?
Cl1_5 O3_5 1.434(3) . ?
Cl1_5 O4_5 1.436(2) . ?
O1W H1W 0.86(4) . ?
O1W H2W 0.89(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1_1 Cu1_1 N2_1 94.09(9) . . ?
N1_1 Cu1_1 N3_1 169.76(8) . . ?
N2_1 Cu1_1 N3_1 86.41(9) . . ?
N1_1 Cu1_1 N4_1 86.57(9) . . ?
N2_1 Cu1_1 N4_1 163.81(8) . . ?
N3_1 Cu1_1 N4_1 95.81(9) . . ?
N1_1 Cu1_1 C12_1 56.66(8) . . ?
N2_1 Cu1_1 C12_1 97.91(8) . . ?
N3_1 Cu1_1 C12_1 113.12(8) . . ?
N4_1 Cu1_1 C12_1 95.95(8) . . ?
N1_1 Cu1_1 O1_3 98.48(7) . . ?
N2_1 Cu1_1 O1_3 81.49(7) . . ?
N3_1 Cu1_1 O1_3 91.72(7) . . ?
N4_1 Cu1_1 O1_3 82.41(7) . . ?
C12_1 Cu1_1 O1_3 155.11(7) . . ?
N1_1 Cu1_1 C13_1 76.39(8) . . ?
N2_1 Cu1_1 C13_1 103.04(8) . . ?
N3_1 Cu1_1 C13_1 93.52(8) . . ?
N4_1 Cu1_1 C13_1 92.85(8) . . ?
C12_1 Cu1_1 C13_1 20.39(8) . . ?
O1_3 Cu1_1 C13_1 173.28(7) . . ?
C1_1 N1_1 C11_1 110.2(2) . . ?
C1_1 N1_1 C10_1 108.4(2) . . ?
C11_1 N1_1 C10_1 108.9(2) . . ?
C1_1 N1_1 Cu1_1 114.29(16) . . ?
C11_1 N1_1 Cu1_1 108.58(15) . . ?
C10_1 N1_1 Cu1_1 106.33(15) . . ?
C4_1 N2_1 C3_1 108.44(19) . . ?
C4_1 N2_1 C14_1 110.2(2) . . ?
C3_1 N2_1 C14_1 109.5(2) . . ?
C4_1 N2_1 Cu1_1 100.72(15) . . ?
C3_1 N2_1 Cu1_1 113.78(16) . . ?
C14_1 N2_1 Cu1_1 113.73(16) . . ?
C6_1 N3_1 C17_1 111.6(2) . . ?
C6_1 N3_1 C5_1 107.4(2) . . ?
C17_1 N3_1 C5_1 108.4(2) . . ?
C6_1 N3_1 Cu1_1 109.98(15) . . ?
C17_1 N3_1 Cu1_1 112.33(15) . . ?
C5_1 N3_1 Cu1_1 106.89(15) . . ?
C9_1 N4_1 C8_1 108.90(19) . . ?
C9_1 N4_1 C20_1 110.7(2) . . ?
C8_1 N4_1 C20_1 108.3(2) . . ?
C9_1 N4_1 Cu1_1 100.82(15) . . ?
C8_1 N4_1 Cu1_1 113.10(16) . . ?
C20_1 N4_1 Cu1_1 114.82(15) . . ?
N1_1 C1_1 C2_1 115.4(2) . . ?
N1_1 C1_1 H1A_1 108.4 . . ?
C2_1 C1_1 H1A_1 108.4 . . ?
N1_1 C1_1 H1B_1 108.4 . . ?
C2_1 C1_1 H1B_1 108.4 . . ?
H1A_1 C1_1 H1B_1 107.5 . . ?
C3_1 C2_1 C1_1 115.1(2) . . ?
C3_1 C2_1 H2A_1 108.5 . . ?
C1_1 C2_1 H2A_1 108.5 . . ?
C3_1 C2_1 H2B_1 108.5 . . ?
C1_1 C2_1 H2B_1 108.5 . . ?
H2A_1 C2_1 H2B_1 107.5 . . ?
N2_1 C3_1 C2_1 114.3(2) . . ?
N2_1 C3_1 H3A_1 108.7 . . ?
C2_1 C3_1 H3A_1 108.7 . . ?
N2_1 C3_1 H3B_1 108.7 . . ?
C2_1 C3_1 H3B_1 108.7 . . ?
H3A_1 C3_1 H3B_1 107.6 . . ?
N2_1 C4_1 C5_1 109.3(2) . . ?
N2_1 C4_1 H4A_1 109.8 . . ?
C5_1 C4_1 H4A_1 109.8 . . ?
N2_1 C4_1 H4B_1 109.8 . . ?
C5_1 C4_1 H4B_1 109.8 . . ?
H4A_1 C4_1 H4B_1 108.3 . . ?
N3_1 C5_1 C4_1 109.1(2) . . ?
N3_1 C5_1 H5A_1 109.9 . . ?
C4_1 C5_1 H5A_1 109.9 . . ?
N3_1 C5_1 H5B_1 109.9 . . ?
C4_1 C5_1 H5B_1 109.9 . . ?
H5A_1 C5_1 H5B_1 108.3 . . ?
N3_1 C6_1 C7_1 115.3(2) . . ?
N3_1 C6_1 H6A_1 108.5 . . ?
C7_1 C6_1 H6A_1 108.5 . . ?
N3_1 C6_1 H6B_1 108.5 . . ?
C7_1 C6_1 H6B_1 108.5 . . ?
H6A_1 C6_1 H6B_1 107.5 . . ?
C6_1 C7_1 C8_1 114.8(2) . . ?
C6_1 C7_1 H7A_1 108.6 . . ?
C8_1 C7_1 H7A_1 108.6 . . ?
C6_1 C7_1 H7B_1 108.6 . . ?
C8_1 C7_1 H7B_1 108.6 . . ?
H7A_1 C7_1 H7B_1 107.5 . . ?
N4_1 C8_1 C7_1 113.5(2) . . ?
N4_1 C8_1 H8A_1 108.9 . . ?
C7_1 C8_1 H8A_1 108.9 . . ?
N4_1 C8_1 H8B_1 108.9 . . ?
C7_1 C8_1 H8B_1 108.9 . . ?
H8A_1 C8_1 H8B_1 107.7 . . ?
N4_1 C9_1 C10_1 108.5(2) . . ?
N4_1 C9_1 H9A_1 110.0 . . ?
C10_1 C9_1 H9A_1 110.0 . . ?
N4_1 C9_1 H9B_1 110.0 . . ?
C10_1 C9_1 H9B_1 110.0 . . ?
H9A_1 C9_1 H9B_1 108.4 . . ?
N1_1 C10_1 C9_1 109.5(2) . . ?
N1_1 C10_1 H10A_1 109.8 . . ?
C9_1 C10_1 H10A_1 109.8 . . ?
N1_1 C10_1 H10B_1 109.8 . . ?
C9_1 C10_1 H10B_1 109.8 . . ?
H10A_1 C10_1 H10B_1 108.2 . . ?
C12_1 C11_1 N1_1 110.3(2) . . ?
C12_1 C11_1 H11A_1 109.6 . . ?
N1_1 C11_1 H11A_1 109.6 . . ?
C12_1 C11_1 H11B_1 109.6 . . ?
N1_1 C11_1 H11B_1 109.6 . . ?
H11A_1 C11_1 H11B_1 108.1 . . ?
C13_1 C12_1 C11_1 179.2(3) . . ?
C13_1 C12_1 Cu1_1 102.1(2) . . ?
C11_1 C12_1 Cu1_1 77.31(14) . . ?
C12_1 C13_1 Cu1_1 57.49(17) . . ?
C12_1 C13_1 H13_1 180.0 . . ?
Cu1_1 C13_1 H13_1 122.5 . . ?
C15_1 C14_1 N2_1 111.5(2) . . ?
C15_1 C14_1 H14A_1 109.3 . . ?
N2_1 C14_1 H14A_1 109.3 . . ?
C15_1 C14_1 H14B_1 109.3 . . ?
N2_1 C14_1 H14B_1 109.3 . . ?
H14A_1 C14_1 H14B_1 108.0 . . ?
C16_1 C15_1 C14_1 174.4(3) . . ?
C15_1 C16_1 H16_1 180.0 . . ?
C18_1 C17_1 N3_1 112.4(2) . . ?
C18_1 C17_1 H17A_1 109.1 . . ?
N3_1 C17_1 H17A_1 109.1 . . ?
C18_1 C17_1 H17B_1 109.1 . . ?
N3_1 C17_1 H17B_1 109.1 . . ?
H17A_1 C17_1 H17B_1 107.9 . . ?
C19_1 C18_1 C17_1 177.4(3) . . ?
C18_1 C19_1 H19_1 180.0 . . ?
C21_1 C20_1 N4_1 113.0(2) . . ?
C21_1 C20_1 H20A_1 109.0 . . ?
N4_1 C20_1 H20A_1 109.0 . . ?
C21_1 C20_1 H20B_1 109.0 . . ?
N4_1 C20_1 H20B_1 109.0 . . ?
H20A_1 C20_1 H20B_1 107.8 . . ?
C22_1 C21_1 C20_1 178.9(3) . . ?
C21_1 C22_1 H22_1 180.0 . . ?
N1_2 Cu1_2 N1_2 180.0 . 2_565 ?
N1_2 Cu1_2 N2_2 86.13(9) . 2_565 ?
N1_2 Cu1_2 N2_2 93.87(9) 2_565 2_565 ?
N1_2 Cu1_2 N2_2 93.87(9) . . ?
N1_2 Cu1_2 N2_2 86.13(9) 2_565 . ?
N2_2 Cu1_2 N2_2 180.0 2_565 . ?
N1_2 Cu1_2 C7_2 59.15(9) . . ?
N1_2 Cu1_2 C7_2 120.85(9) 2_565 . ?
N2_2 Cu1_2 C7_2 89.41(8) 2_565 . ?
N2_2 Cu1_2 C7_2 90.59(8) . . ?
N1_2 Cu1_2 C8_2 80.29(9) . . ?
N1_2 Cu1_2 C8_2 99.71(9) 2_565 . ?
N2_2 Cu1_2 C8_2 87.77(8) 2_565 . ?
N2_2 Cu1_2 C8_2 92.23(8) . . ?
C7_2 Cu1_2 C8_2 21.35(9) . . ?
C1_2 N1_2 C5_2 108.0(2) . . ?
C1_2 N1_2 C6_2 110.9(2) . . ?
C5_2 N1_2 C6_2 109.2(2) . . ?
C1_2 N1_2 Cu1_2 114.56(17) . . ?
C5_2 N1_2 Cu1_2 105.96(15) . . ?
C6_2 N1_2 Cu1_2 108.04(16) . . ?
C3_2 N2_2 C4_2 109.3(2) . . ?
C3_2 N2_2 C9_2 110.6(2) . . ?
C4_2 N2_2 C9_2 107.7(2) . . ?
C3_2 N2_2 Cu1_2 107.56(16) . . ?
C4_2 N2_2 Cu1_2 103.69(15) . . ?
C9_2 N2_2 Cu1_2 117.55(16) . . ?
N1_2 C1_2 C2_2 115.1(2) . . ?
N1_2 C1_2 H1A_2 108.5 . . ?
C2_2 C1_2 H1A_2 108.5 . . ?
N1_2 C1_2 H1B_2 108.5 . . ?
C2_2 C1_2 H1B_2 108.5 . . ?
H1A_2 C1_2 H1B_2 107.5 . . ?
C3_2 C2_2 C1_2 114.8(2) . . ?
C3_2 C2_2 H2A_2 108.6 . . ?
C1_2 C2_2 H2A_2 108.6 . . ?
C3_2 C2_2 H2B_2 108.6 . . ?
C1_2 C2_2 H2B_2 108.6 . . ?
H2A_2 C2_2 H2B_2 107.5 . . ?
N2_2 C3_2 C2_2 113.2(2) . . ?
N2_2 C3_2 H3A_2 108.9 . . ?
C2_2 C3_2 H3A_2 108.9 . . ?
N2_2 C3_2 H3B_2 108.9 . . ?
C2_2 C3_2 H3B_2 108.9 . . ?
H3A_2 C3_2 H3B_2 107.8 . . ?
N2_2 C4_2 C5_2 108.5(2) . 2_565 ?
N2_2 C4_2 H4A_2 110.0 . . ?
C5_2 C4_2 H4A_2 110.0 2_565 . ?
N2_2 C4_2 H4B_2 110.0 . . ?
C5_2 C4_2 H4B_2 110.0 2_565 . ?
H4A_2 C4_2 H4B_2 108.4 . . ?
N1_2 C5_2 C4_2 109.0(2) . 2_565 ?
N1_2 C5_2 H5A_2 109.9 . . ?
C4_2 C5_2 H5A_2 109.9 2_565 . ?
N1_2 C5_2 H5B_2 109.9 . . ?
C4_2 C5_2 H5B_2 109.9 2_565 . ?
H5A_2 C5_2 H5B_2 108.3 . . ?
C7_2 C6_2 N1_2 111.3(2) . . ?
C7_2 C6_2 H6A_2 109.4 . . ?
N1_2 C6_2 H6A_2 109.4 . . ?
C7_2 C6_2 H6B_2 109.4 . . ?
N1_2 C6_2 H6B_2 109.4 . . ?
H6A_2 C6_2 H6B_2 108.0 . . ?
C8_2 C7_2 C6_2 178.0(3) . . ?
C8_2 C7_2 Cu1_2 99.3(2) . . ?
C6_2 C7_2 Cu1_2 78.99(15) . . ?
C7_2 C8_2 Cu1_2 59.33(19) . . ?
C7_2 C8_2 H11C_2 180.0 . . ?
Cu1_2 C8_2 H11C_2 120.7 . . ?
C10_2 C9_2 N2_2 111.9(2) . . ?
C10_2 C9_2 H9A_2 109.2 . . ?
N2_2 C9_2 H9A_2 109.2 . . ?
C10_2 C9_2 H9B_2 109.2 . . ?
N2_2 C9_2 H9B_2 109.2 . . ?
H9A_2 C9_2 H9B_2 107.9 . . ?
C11_2 C10_2 C9_2 175.5(3) . . ?
C10_2 C11_2 H11A_2 180.0 . . ?
O3_3 Cl1_3 O2_3 111.50(18) . . ?
O3_3 Cl1_3 O4_3 108.66(16) . . ?
O2_3 Cl1_3 O4_3 110.16(17) . . ?
O3_3 Cl1_3 O1_3 109.68(16) . . ?
O2_3 Cl1_3 O1_3 109.46(14) . . ?
O4_3 Cl1_3 O1_3 107.28(13) . . ?
Cl1_3 O1_3 Cu1_1 151.01(13) . . ?
O1_4 Cl1_4 O2_4 109.70(19) . . ?
O1_4 Cl1_4 O3_4 107.8(2) . . ?
O2_4 Cl1_4 O3_4 112.51(16) . . ?
O1_4 Cl1_4 O4_4 106.9(3) . . ?
O2_4 Cl1_4 O4_4 110.24(18) . . ?
O3_4 Cl1_4 O4_4 109.46(19) . . ?
O1_5 Cl1_5 O2_5 111.9(2) . . ?
O1_5 Cl1_5 O3_5 108.1(2) . . ?
O2_5 Cl1_5 O3_5 108.0(2) . . ?
O1_5 Cl1_5 O4_5 111.05(18) . . ?
O2_5 Cl1_5 O4_5 110.59(16) . . ?
O3_5 Cl1_5 O4_5 106.99(17) . . ?
H1W O1W H2W 101(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C11_1 N1_1 C1_1 C2_1 65.8(3) . . . . ?
C10_1 N1_1 C1_1 C2_1 -175.1(2) . . . . ?
Cu1_1 N1_1 C1_1 C2_1 -56.7(3) . . . . ?
N1_1 C1_1 C2_1 C3_1 64.4(3) . . . . ?
C4_1 N2_1 C3_1 C2_1 170.5(2) . . . . ?
C14_1 N2_1 C3_1 C2_1 -69.2(3) . . . . ?
Cu1_1 N2_1 C3_1 C2_1 59.3(3) . . . . ?
C1_1 C2_1 C3_1 N2_1 -65.6(3) . . . . ?
C3_1 N2_1 C4_1 C5_1 -172.8(2) . . . . ?
C14_1 N2_1 C4_1 C5_1 67.3(3) . . . . ?
Cu1_1 N2_1 C4_1 C5_1 -53.1(2) . . . . ?
C6_1 N3_1 C5_1 C4_1 91.7(2) . . . . ?
C17_1 N3_1 C5_1 C4_1 -147.5(2) . . . . ?
Cu1_1 N3_1 C5_1 C4_1 -26.2(2) . . . . ?
N2_1 C4_1 C5_1 N3_1 55.5(3) . . . . ?
C17_1 N3_1 C6_1 C7_1 64.0(3) . . . . ?
C5_1 N3_1 C6_1 C7_1 -177.3(2) . . . . ?
Cu1_1 N3_1 C6_1 C7_1 -61.4(2) . . . . ?
N3_1 C6_1 C7_1 C8_1 70.5(3) . . . . ?
C9_1 N4_1 C8_1 C7_1 168.6(2) . . . . ?
C20_1 N4_1 C8_1 C7_1 -71.1(3) . . . . ?
Cu1_1 N4_1 C8_1 C7_1 57.4(3) . . . . ?
C6_1 C7_1 C8_1 N4_1 -66.6(3) . . . . ?
C8_1 N4_1 C9_1 C10_1 -172.0(2) . . . . ?
C20_1 N4_1 C9_1 C10_1 69.1(3) . . . . ?
Cu1_1 N4_1 C9_1 C10_1 -52.8(2) . . . . ?
C1_1 N1_1 C10_1 C9_1 94.9(2) . . . . ?
C11_1 N1_1 C10_1 C9_1 -145.2(2) . . . . ?
Cu1_1 N1_1 C10_1 C9_1 -28.4(2) . . . . ?
N4_1 C9_1 C10_1 N1_1 56.9(3) . . . . ?
C1_1 N1_1 C11_1 C12_1 -155.7(2) . . . . ?
C10_1 N1_1 C11_1 C12_1 85.5(3) . . . . ?
Cu1_1 N1_1 C11_1 C12_1 -29.9(3) . . . . ?
N1_1 C11_1 C12_1 Cu1_1 20.42(18) . . . . ?
C4_1 N2_1 C14_1 C15_1 53.9(3) . . . . ?
C3_1 N2_1 C14_1 C15_1 -65.3(3) . . . . ?
Cu1_1 N2_1 C14_1 C15_1 166.13(18) . . . . ?
C6_1 N3_1 C17_1 C18_1 55.2(3) . . . . ?
C5_1 N3_1 C17_1 C18_1 -62.8(3) . . . . ?
Cu1_1 N3_1 C17_1 C18_1 179.31(19) . . . . ?
C9_1 N4_1 C20_1 C21_1 51.3(3) . . . . ?
C8_1 N4_1 C20_1 C21_1 -68.0(3) . . . . ?
Cu1_1 N4_1 C20_1 C21_1 164.56(18) . . . . ?
C5_2 N1_2 C1_2 C2_2 -173.0(2) . . . . ?
C6_2 N1_2 C1_2 C2_2 67.4(3) . . . . ?
Cu1_2 N1_2 C1_2 C2_2 -55.2(3) . . . . ?
N1_2 C1_2 C2_2 C3_2 63.2(3) . . . . ?
C4_2 N2_2 C3_2 C2_2 179.1(2) . . . . ?
C9_2 N2_2 C3_2 C2_2 -62.5(3) . . . . ?
Cu1_2 N2_2 C3_2 C2_2 67.2(2) . . . . ?
C1_2 C2_2 C3_2 N2_2 -72.6(3) . . . . ?
C3_2 N2_2 C4_2 C5_2 -155.8(2) . . . 2_565 ?
C9_2 N2_2 C4_2 C5_2 84.0(3) . . . 2_565 ?
Cu1_2 N2_2 C4_2 C5_2 -41.3(2) . . . 2_565 ?
C1_2 N1_2 C5_2 C4_2 166.5(2) . . . 2_565 ?
C6_2 N1_2 C5_2 C4_2 -72.8(3) . . . 2_565 ?
Cu1_2 N1_2 C5_2 C4_2 43.3(3) . . . 2_565 ?
C1_2 N1_2 C6_2 C7_2 -143.7(2) . . . . ?
C5_2 N1_2 C6_2 C7_2 97.4(3) . . . . ?
Cu1_2 N1_2 C6_2 C7_2 -17.4(3) . . . . ?
N1_2 C6_2 C7_2 Cu1_2 12.23(19) . . . . ?
C3_2 N2_2 C9_2 C10_2 -46.7(3) . . . . ?
C4_2 N2_2 C9_2 C10_2 72.7(3) . . . . ?
Cu1_2 N2_2 C9_2 C10_2 -170.75(18) . . . . ?
O3_3 Cl1_3 O1_3 Cu1_1 -144.4(3) . . . . ?
O2_3 Cl1_3 O1_3 Cu1_1 93.0(3) . . . . ?
O4_3 Cl1_3 O1_3 Cu1_1 -26.5(3) . . . . ?

_refine_diff_density_max         0.949
_refine_diff_density_min         -0.605
_refine_diff_density_rms         0.072

####################################################################### 
# 
# 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_mht10rm3m_face
_database_code_depnum_ccdc_archive 'CCDC 2012634'
loop_
_audit_author_name
_audit_author_address
'Peter Turner'
;University of Sydney
Australia
;
_audit_update_record             
;
2020-06-28 deposited with the CCDC.	2021-02-26 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         ?
_chemical_formula_sum            'C13.25 H27 Cl2 Cu N4 O8.25'
_chemical_formula_weight         508.83

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'
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'
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'
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15

_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, -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                   31.689(5)
_cell_length_b                   8.5129(12)
_cell_length_c                   16.517(2)
_cell_angle_alpha                90
_cell_angle_beta                 112.422(2)
_cell_angle_gamma                90
_cell_volume                     4118.9(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    150.0(5)
_cell_measurement_reflns_used    7362
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      28.3

_exptl_crystal_description       plate
_exptl_crystal_colour            purple
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_F_000             2108
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    1.370
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_max  0.928
_exptl_absorpt_correction_T_min  0.729
_exptl_absorpt_correction_type   Gaussian
_exptl_absorpt_process_details   
;
 SADABS (Bruker,2008) was used to apply a Gaussian absorption correction
 using indexed crystal faces, followed by a multiscan absorption correction.
 A Lambda/2 correction factor = 0.0015 was applied to the data.
;


_exptl_crystal_preparation       
;
 Attached with Exxon Paratone N oil to a short length of fibre 
 supported on a thin piece of copper wire inserted in a copper 
 mounting pin. The crystal was quenched in a cold nitrogen gas 
 stream from an Oxford Cryosystems Cryostream.
;


_diffrn_ambient_temperature      150.0(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           'Mo K\a'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19982
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.492
_diffrn_reflns_theta_max         28.895
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.931
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.931
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5064
_reflns_number_gt                4234
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'SMART (Bruker,1995)'
_computing_cell_refinement       'SAINT (Bruker,1995)'
_computing_data_reduction        'SAINT and XPREP (Bruker 1995)'
_computing_structure_solution    
"Charge Flipping (Oszlányi & Sütiő, 2008)"
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
  OLEX2 (Dolomanov,O.V.et al., 2009)
  shelXle (Hübschle,C.B., et al., 2011) 
;
_computing_publication_material  'WinGX (Farrugia, 1999)'


_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)+(0.03P)²+4.0P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5064
_refine_ls_number_parameters     266
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0907
_refine_ls_wR_factor_gt          0.0873
_refine_ls_goodness_of_fit_ref   1.362
_refine_ls_restrained_S_all      1.365
_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 0.12713(2) 0.32043(3) 0.04103(2) 0.01991(8) Uani 1 1 d . . . . .
N1 N 0.19485(6) 0.3519(2) 0.12489(12) 0.0224(4) Uani 1 1 d . . . . .
N2 N 0.13839(7) 0.4907(2) -0.03313(13) 0.0277(4) Uani 1 1 d . . . . .
H2N H 0.124986 0.589227 -0.020141 0.033 Uiso 1 1 calc R U . . .
N3 N 0.06128(7) 0.2904(2) -0.04175(13) 0.0286(4) Uani 1 1 d . . . . .
H3N H 0.043311 0.376364 -0.028651 0.034 Uiso 1 1 calc R U . . .
N4 N 0.11352(7) 0.1594(2) 0.11657(13) 0.0263(4) Uani 1 1 d . . . . .
H4N H 0.126816 0.057724 0.107301 0.032 Uiso 1 1 calc R U . . .
C1 C 0.20734(8) 0.5068(3) 0.09739(17) 0.0285(5) Uani 1 1 d . . . . .
H1A H 0.240961 0.518227 0.120718 0.034 Uiso 1 1 calc R U . . .
H1B H 0.194626 0.593170 0.121296 0.034 Uiso 1 1 calc R U . . .
C2 C 0.18859(8) 0.5160(3) -0.00086(17) 0.0317(5) Uani 1 1 d . . . . .
H2B H 0.195239 0.620279 -0.019792 0.038 Uiso 1 1 calc R U . . .
H2A H 0.202860 0.434573 -0.024916 0.038 Uiso 1 1 calc R U . . .
C3 C 0.11798(10) 0.4695(3) -0.12940(16) 0.0369(6) Uani 1 1 d . . . . .
H3A H 0.131165 0.374797 -0.145484 0.044 Uiso 1 1 calc R U . . .
H3B H 0.125649 0.561232 -0.158038 0.044 Uiso 1 1 calc R U . . .
C4 C 0.06637(10) 0.4522(3) -0.16252(17) 0.0391(6) Uani 1 1 d . . . . .
H4A H 0.053564 0.461623 -0.227149 0.047 Uiso 1 1 calc R U . . .
H4B H 0.053880 0.539567 -0.138864 0.047 Uiso 1 1 calc R U . . .
C5 C 0.05076(9) 0.2971(3) -0.13730(16) 0.0367(6) Uani 1 1 d . . . . .
H5B H 0.017457 0.285019 -0.169762 0.044 Uiso 1 1 calc R U . . .
H5A H 0.066236 0.209166 -0.153971 0.044 Uiso 1 1 calc R U . . .
C6 C 0.04586(9) 0.1417(3) -0.01593(18) 0.0354(6) Uani 1 1 d . . . . .
H6A H 0.058240 0.051066 -0.037359 0.042 Uiso 1 1 calc R U . . .
H6B H 0.012117 0.135483 -0.041478 0.042 Uiso 1 1 calc R U . . .
C7 C 0.06285(9) 0.1388(3) 0.08181(18) 0.0332(6) Uani 1 1 d . . . . .
H7A H 0.054972 0.037578 0.102000 0.040 Uiso 1 1 calc R U . . .
H7B H 0.048627 0.224716 0.102987 0.040 Uiso 1 1 calc R U . . .
C8 C 0.13174(9) 0.1887(3) 0.21179(16) 0.0330(6) Uani 1 1 d . . . . .
H8A H 0.124126 0.098389 0.241452 0.040 Uiso 1 1 calc R U . . .
H8B H 0.116739 0.283040 0.223670 0.040 Uiso 1 1 calc R U . . .
C9 C 0.18278(9) 0.2131(3) 0.24972(16) 0.0338(6) Uani 1 1 d . . . . .
H9A H 0.197359 0.120171 0.235255 0.041 Uiso 1 1 calc R U . . .
H9B H 0.193129 0.217863 0.314300 0.041 Uiso 1 1 calc R U . . .
C10 C 0.19973(8) 0.3592(3) 0.21871(15) 0.0286(5) Uani 1 1 d . . . . .
H10B H 0.182565 0.451231 0.226510 0.034 Uiso 1 1 calc R U . . .
H10A H 0.232317 0.375252 0.256082 0.034 Uiso 1 1 calc R U . . .
C11 C 0.22569(8) 0.2276(3) 0.11382(16) 0.0260(5) Uani 1 1 d . . . . .
H11A H 0.215601 0.123819 0.126701 0.031 Uiso 1 1 calc R U . . .
H11B H 0.222871 0.226695 0.052027 0.031 Uiso 1 1 calc R U . . .
C12 C 0.27406(8) 0.2510(3) 0.17105(17) 0.0293(5) Uani 1 1 d . . . . .
C13 C 0.31263(9) 0.2712(3) 0.21802(18) 0.0355(6) Uani 1 1 d . . . . .
H13A H 0.343574 0.287328 0.255711 0.043 Uiso 1 1 calc R U . . .
O1MA O -0.0037(7) 0.1738(16) 0.2294(10) 0.039(3) Uiso 0.125 1 d D . P A -1
H1MA H -0.015006 0.147981 0.176327 0.059 Uiso 0.125 1 d R U P A -1
C1MA C 0.0297(8) 0.062(3) 0.2789(16) 0.039(3) Uiso 0.125 1 d D . P A -1
H1M1 H 0.059625 0.099398 0.282592 0.059 Uiso 0.125 1 d R U P A -1
H1M2 H 0.023025 -0.039503 0.248763 0.059 Uiso 0.125 1 d R U P A -1
H1M3 H 0.029942 0.050028 0.338133 0.059 Uiso 0.125 1 d R U P A -1
O1MB O 0.0083(5) 0.1249(18) 0.2451(16) 0.039(3) Uiso 0.125 1 d D . P B -2
H1MB H 0.021936 0.190086 0.284580 0.059 Uiso 0.125 1 d R U P B -2
C1MB C -0.0375(6) 0.097(3) 0.2378(17) 0.039(3) Uiso 0.125 1 d D . P B -2
H1M4 H -0.036206 0.043577 0.291269 0.059 Uiso 0.125 1 d R U P B -2
H1M5 H -0.054770 0.032582 0.186737 0.059 Uiso 0.125 1 d R U P B -2
H1M6 H -0.052539 0.199060 0.233201 0.059 Uiso 0.125 1 d R U P B -2
Cl1 Cl 0.15896(2) -0.05783(7) -0.03025(4) 0.02875(14) Uani 1 1 d . . . C -2
O1 O 0.14477(7) 0.1052(2) -0.04576(12) 0.0360(4) Uani 1 1 d . . . C -2
O2 O 0.16109(7) -0.1040(2) 0.05504(12) 0.0389(4) Uani 1 1 d . . . C -2
O3 O 0.20307(7) -0.0742(2) -0.03435(15) 0.0460(5) Uani 1 1 d . . . C -2
O4 O 0.12648(8) -0.1559(2) -0.09497(14) 0.0480(5) Uani 1 1 d . . . C -2
Cl2 Cl 0.06950(2) 0.64137(7) 0.09836(4) 0.02635(13) Uani 1 1 d . . . D -2
O5 O 0.11047(6) 0.5463(2) 0.12490(13) 0.0400(5) Uani 1 1 d . . . D -2
O6 O 0.07669(7) 0.7673(2) 0.15959(13) 0.0414(5) Uani 1 1 d . . . D -2
O7 O 0.05948(8) 0.7004(3) 0.01222(14) 0.0545(6) Uani 1 1 d . . . D -2
O8 O 0.03270(6) 0.5450(2) 0.09866(14) 0.0434(5) Uani 1 1 d . . . D -2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N4 2.008(2) . ?
Cu1 N2 2.015(2) . ?
Cu1 N3 2.0281(19) . ?
Cu1 N1 2.0802(19) . ?
N1 C1 1.496(3) . ?
N1 C11 1.498(3) . ?
N1 C10 1.499(3) . ?
N2 C3 1.481(3) . ?
N2 C2 1.488(3) . ?
N2 H2N 1.0000 . ?
N3 C6 1.477(3) . ?
N3 C5 1.485(3) . ?
N3 H3N 1.0000 . ?
N4 C8 1.475(3) . ?
N4 C7 1.495(3) . ?
N4 H4N 1.0000 . ?
C1 C2 1.502(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2B 0.9900 . ?
C2 H2A 0.9900 . ?
C3 C4 1.521(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.523(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5B 0.9900 . ?
C5 H5A 0.9900 . ?
C6 C7 1.495(4) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.509(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.519(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10B 0.9900 . ?
C10 H10A 0.9900 . ?
C11 C12 1.476(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.184(4) . ?
C13 H13A 0.9500 . ?
O1MA C1MA 1.426(17) . ?
O1MA H1MA 0.8400 . ?
C1MA H1M1 0.9800 . ?
C1MA H1M2 0.9800 . ?
C1MA H1M3 0.9800 . ?
O1MB C1MB 1.428(18) . ?
O1MB H1MB 0.8400 . ?
C1MB H1M4 0.9800 . ?
C1MB H1M5 0.9800 . ?
C1MB H1M6 0.9800 . ?
Cl1 O3 1.432(2) . ?
Cl1 O4 1.435(2) . ?
Cl1 O2 1.4391(19) . ?
Cl1 O1 1.4514(18) . ?
Cl2 O7 1.426(2) . ?
Cl2 O8 1.4274(19) . ?
Cl2 O6 1.4310(19) . ?
Cl2 O5 1.4487(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 Cu1 N2 176.69(8) . . ?
N4 Cu1 N3 85.60(8) . . ?
N2 Cu1 N3 93.21(8) . . ?
N4 Cu1 N1 94.92(8) . . ?
N2 Cu1 N1 86.29(8) . . ?
N3 Cu1 N1 179.43(8) . . ?
C1 N1 C11 108.96(18) . . ?
C1 N1 C10 110.04(18) . . ?
C11 N1 C10 109.91(18) . . ?
C1 N1 Cu1 103.68(14) . . ?
C11 N1 Cu1 112.53(14) . . ?
C10 N1 Cu1 111.54(14) . . ?
C3 N2 C2 111.8(2) . . ?
C3 N2 Cu1 117.33(16) . . ?
C2 N2 Cu1 107.43(14) . . ?
C3 N2 H2N 106.6 . . ?
C2 N2 H2N 106.6 . . ?
Cu1 N2 H2N 106.6 . . ?
C6 N3 C5 112.0(2) . . ?
C6 N3 Cu1 106.37(15) . . ?
C5 N3 Cu1 117.90(16) . . ?
C6 N3 H3N 106.6 . . ?
C5 N3 H3N 106.6 . . ?
Cu1 N3 H3N 106.6 . . ?
C8 N4 C7 110.82(19) . . ?
C8 N4 Cu1 117.23(15) . . ?
C7 N4 Cu1 107.18(15) . . ?
C8 N4 H4N 107.0 . . ?
C7 N4 H4N 107.0 . . ?
Cu1 N4 H4N 107.0 . . ?
N1 C1 C2 109.43(19) . . ?
N1 C1 H1A 109.8 . . ?
C2 C1 H1A 109.8 . . ?
N1 C1 H1B 109.8 . . ?
C2 C1 H1B 109.8 . . ?
H1A C1 H1B 108.2 . . ?
N2 C2 C1 107.90(19) . . ?
N2 C2 H2B 110.1 . . ?
C1 C2 H2B 110.1 . . ?
N2 C2 H2A 110.1 . . ?
C1 C2 H2A 110.1 . . ?
H2B C2 H2A 108.4 . . ?
N2 C3 C4 111.5(2) . . ?
N2 C3 H3A 109.3 . . ?
C4 C3 H3A 109.3 . . ?
N2 C3 H3B 109.3 . . ?
C4 C3 H3B 109.3 . . ?
H3A C3 H3B 108.0 . . ?
C3 C4 C5 113.7(2) . . ?
C3 C4 H4A 108.8 . . ?
C5 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
C5 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
N3 C5 C4 111.1(2) . . ?
N3 C5 H5B 109.4 . . ?
C4 C5 H5B 109.4 . . ?
N3 C5 H5A 109.4 . . ?
C4 C5 H5A 109.4 . . ?
H5B C5 H5A 108.0 . . ?
N3 C6 C7 107.6(2) . . ?
N3 C6 H6A 110.2 . . ?
C7 C6 H6A 110.2 . . ?
N3 C6 H6B 110.2 . . ?
C7 C6 H6B 110.2 . . ?
H6A C6 H6B 108.5 . . ?
C6 C7 N4 107.7(2) . . ?
C6 C7 H7A 110.2 . . ?
N4 C7 H7A 110.2 . . ?
C6 C7 H7B 110.2 . . ?
N4 C7 H7B 110.2 . . ?
H7A C7 H7B 108.5 . . ?
N4 C8 C9 112.8(2) . . ?
N4 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
N4 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C8 C9 C10 115.7(2) . . ?
C8 C9 H9A 108.4 . . ?
C10 C9 H9A 108.4 . . ?
C8 C9 H9B 108.4 . . ?
C10 C9 H9B 108.4 . . ?
H9A C9 H9B 107.4 . . ?
N1 C10 C9 113.87(19) . . ?
N1 C10 H10B 108.8 . . ?
C9 C10 H10B 108.8 . . ?
N1 C10 H10A 108.8 . . ?
C9 C10 H10A 108.8 . . ?
H10B C10 H10A 107.7 . . ?
C12 C11 N1 113.14(19) . . ?
C12 C11 H11A 109.0 . . ?
N1 C11 H11A 109.0 . . ?
C12 C11 H11B 109.0 . . ?
N1 C11 H11B 109.0 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 C11 178.8(3) . . ?
C12 C13 H13A 180.0 . . ?
C1MA O1MA H1MA 110.6 . . ?
O1MA C1MA H1M1 107.9 . . ?
O1MA C1MA H1M2 109.1 . . ?
H1M1 C1MA H1M2 109.5 . . ?
O1MA C1MA H1M3 111.3 . . ?
H1M1 C1MA H1M3 109.5 . . ?
H1M2 C1MA H1M3 109.5 . . ?
C1MB O1MB H1MB 112.4 . . ?
O1MB C1MB H1M4 108.1 . . ?
O1MB C1MB H1M5 112.4 . . ?
H1M4 C1MB H1M5 109.5 . . ?
O1MB C1MB H1M6 107.9 . . ?
H1M4 C1MB H1M6 109.5 . . ?
H1M5 C1MB H1M6 109.5 . . ?
O3 Cl1 O4 110.11(13) . . ?
O3 Cl1 O2 109.73(13) . . ?
O4 Cl1 O2 108.84(13) . . ?
O3 Cl1 O1 109.09(12) . . ?
O4 Cl1 O1 109.82(12) . . ?
O2 Cl1 O1 109.24(11) . . ?
O7 Cl2 O8 109.57(14) . . ?
O7 Cl2 O6 110.85(14) . . ?
O8 Cl2 O6 109.78(12) . . ?
O7 Cl2 O5 109.35(13) . . ?
O8 Cl2 O5 108.48(12) . . ?
O6 Cl2 O5 108.77(11) . . ?

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
C11 N1 C1 C2 77.3(2) . . . . ?
C10 N1 C1 C2 -162.09(19) . . . . ?
Cu1 N1 C1 C2 -42.7(2) . . . . ?
C3 N2 C2 C1 -169.9(2) . . . . ?
Cu1 N2 C2 C1 -39.8(2) . . . . ?
N1 C1 C2 N2 56.8(2) . . . . ?
C2 N2 C3 C4 -177.0(2) . . . . ?
Cu1 N2 C3 C4 58.2(3) . . . . ?
N2 C3 C4 C5 -70.7(3) . . . . ?
C6 N3 C5 C4 179.2(2) . . . . ?
Cu1 N3 C5 C4 -56.8(3) . . . . ?
C3 C4 C5 N3 69.6(3) . . . . ?
C5 N3 C6 C7 173.4(2) . . . . ?
Cu1 N3 C6 C7 43.3(2) . . . . ?
N3 C6 C7 N4 -56.1(3) . . . . ?
C8 N4 C7 C6 169.0(2) . . . . ?
Cu1 N4 C7 C6 39.9(2) . . . . ?
C7 N4 C8 C9 -179.0(2) . . . . ?
Cu1 N4 C8 C9 -55.6(3) . . . . ?
N4 C8 C9 C10 65.6(3) . . . . ?
C1 N1 C10 C9 173.58(19) . . . . ?
C11 N1 C10 C9 -66.4(2) . . . . ?
Cu1 N1 C10 C9 59.1(2) . . . . ?
C8 C9 C10 N1 -70.0(3) . . . . ?
C1 N1 C11 C12 63.9(2) . . . . ?
C10 N1 C11 C12 -56.8(3) . . . . ?
Cu1 N1 C11 C12 178.29(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2N O4^b 1.00 2.51 3.154(3) 122.1 1_565 yes
N2 H2N O7^b 1.00 2.52 3.381(3) 144.4 . yes
N3 H3N Cl2^b 1.00 2.98 3.727(2) 132.7 . yes
N3 H3N O8^b 1.00 2.34 3.095(3) 131.8 5_565 yes
N4 H4N Cl1^b 1.00 2.99 3.747(2) 133.4 . yes
N4 H4N O2^b 1.00 2.13 3.083(3) 158.7 . yes
C2 H2B Cl1^b 0.99 2.95 3.732(3) 136.5 1_565 yes
C2 H2B O3^b 0.99 2.63 3.589(3) 162.4 1_565 yes
C3 H3B O4^b 0.99 2.62 3.232(3) 120.1 1_565 yes
C5 H5A O1^b 0.99 2.60 3.224(3) 120.8 . yes
C7 H7A O6^b 0.99 2.48 3.379(3) 150.1 1_545 yes
C10 H10B O5^b 0.99 2.40 3.098(3) 126.8 . yes
C11 H11A Cl1^b 0.99 2.96 3.493(2) 114.5 . yes
C11 H11A O2^b 0.99 2.57 3.404(3) 142.3 . yes

_refine_diff_density_max         1.168
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.087

####################################################################### 
# 
# 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_pjr14ajc_s003d
_database_code_depnum_ccdc_archive 'CCDC 2012630'
loop_
_audit_author_name
_audit_author_address
'Peter Turner'
;University of Sydney
Australia
;
_audit_update_record             
;
2020-06-28 deposited with the CCDC.	2021-02-26 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         'C22 H32 Cl Cu N4 O4, Cl O4'
_chemical_formula_sum            'C22 H32 Cl2 Cu N4 O8'
_chemical_formula_weight         614.95

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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.83120(10)
_cell_length_b                   20.1287(2)
_cell_length_c                   14.5408(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.2560(10)
_cell_angle_gamma                90
_cell_volume                     2577.65(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    28012
_cell_measurement_temperature    150.0(5)
_cell_measurement_theta_max      75.6750
_cell_measurement_theta_min      4.3720

_exptl_crystal_colour            'translucent light blue'
_exptl_crystal_density_diffrn    1.585
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1276
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_exptl_absorpt_coefficient_mu    3.580
_shelx_estimated_absorpt_T_min   0.565
_shelx_estimated_absorpt_T_max   0.763
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 CrysAlisPro, Agilent Technologies,
 Version 1.171.37.33 (compiled Mar 27 2014,17:12:48)
 Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_crystal_treatment        
;
attached with Exxon Paratone N, to a short length 
of fibre supported on a thin piece of copper wire 
inserted in a copper mounting pin.  The crystal was 
quenched in a cold nitrogen gas stream from an 
Oxford Cryosystems Cryostream. 
;

_diffrn_ambient_temperature      150.0(5)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_device       'κ-geometry four circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.5861
_diffrn_reflns_number            73682
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_av_R_equivalents  0.0535
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.757
_diffrn_reflns_theta_max         75.972
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000

_reflns_number_total             5374
_reflns_number_gt                4781
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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_cell_refinement       
;
 CrysAlisPro, Agilent Technologies, Version 1.171.37.33 
 (compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
 CrysAlisPro, Agilent Technologies, Version 1.171.37.33 
 (compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
 CrysAlisPro, Agilent Technologies, Version 1.171.37.33 
 (compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics    
;
  OLEX2 (Dolomanov,O.V.et al., 2009)
  shelXle (Hübschle,C.B., et al., 2011) 
;

_computing_publication_material  
;    
  WinGX (Farrugia, 1999)
;

_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)+(0.03P)²+3.0P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5374
_refine_ls_number_parameters     359
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0409
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0893
_refine_ls_wR_factor_gt          0.0860
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_restrained_S_all      1.161
_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 0.45302(3) 0.25040(2) 0.46260(2) 0.01502(9) Uani 1 1 d . . . . .
N1 N 0.63690(19) 0.31012(9) 0.43852(12) 0.0197(4) Uani 1 1 d . . . . .
N2 N 0.3409(2) 0.32523(9) 0.53125(13) 0.0226(4) Uani 1 1 d . . . . .
N3 N 0.2912(2) 0.18668(9) 0.51424(12) 0.0212(4) Uani 1 1 d . . . . .
N4 N 0.58862(19) 0.17143(9) 0.41667(12) 0.0195(4) Uani 1 1 d . . . . .
C1 C 0.6746(3) 0.36606(12) 0.50463(15) 0.0259(5) Uani 1 1 d . . . . .
H1A H 0.758528 0.392410 0.481579 0.031 Uiso 1 1 calc R U . . .
H1B H 0.711300 0.347081 0.565023 0.031 Uiso 1 1 calc R U . . .
C2 C 0.5437(3) 0.41175(12) 0.51861(17) 0.0301(5) Uani 1 1 d . . . . .
H2A H 0.491688 0.423205 0.458034 0.036 Uiso 1 1 calc R U . . .
H2B H 0.582324 0.453390 0.548042 0.036 Uiso 1 1 calc R U . . .
C3 C 0.4324(3) 0.37971(12) 0.57823(16) 0.0288(5) Uani 1 1 d . . . . .
H3A H 0.488730 0.361380 0.633951 0.035 Uiso 1 1 calc R U . . .
H3B H 0.362352 0.414200 0.598615 0.035 Uiso 1 1 calc R U . . .
C4 C 0.2736(3) 0.28772(13) 0.60708(16) 0.0289(5) Uani 1 1 d . . . . .
H4A H 0.355271 0.273135 0.652954 0.035 Uiso 1 1 calc R U . . .
H4B H 0.203706 0.316965 0.638633 0.035 Uiso 1 1 calc R U . . .
C5 C 0.1897(3) 0.22910(13) 0.56870(17) 0.0293(5) Uani 1 1 d . . . . .
H5A H 0.101027 0.243965 0.528271 0.035 Uiso 1 1 calc R U . . .
H5B H 0.151894 0.202610 0.619589 0.035 Uiso 1 1 calc R U . . .
C6 C 0.3790(3) 0.14049(12) 0.57913(15) 0.0250(5) Uani 1 1 d . . . . .
H6A H 0.306056 0.113752 0.612054 0.030 Uiso 1 1 calc R U . . .
H6B H 0.438932 0.167426 0.625754 0.030 Uiso 1 1 calc R U . . .
C7 C 0.4857(3) 0.09364(11) 0.53460(17) 0.0270(5) Uani 1 1 d . . . . .
H7A H 0.428033 0.070297 0.483306 0.032 Uiso 1 1 calc R U . . .
H7B H 0.521089 0.059706 0.580584 0.032 Uiso 1 1 calc R U . . .
C8 C 0.6236(2) 0.12601(11) 0.49731(15) 0.0237(4) Uani 1 1 d . . . . .
H8A H 0.677984 0.151705 0.547568 0.028 Uiso 1 1 calc R U . . .
H8B H 0.692974 0.090664 0.478626 0.028 Uiso 1 1 calc R U . . .
C9 C 0.7346(2) 0.20234(12) 0.39179(16) 0.0259(5) Uani 1 1 d . . . . .
H9A H 0.818588 0.170018 0.402533 0.031 Uiso 1 1 calc R U . . .
H9B H 0.726785 0.214364 0.325590 0.031 Uiso 1 1 calc R U . . .
C10 C 0.7680(2) 0.26326(12) 0.44899(16) 0.0246(5) Uani 1 1 d . . . . .
H10A H 0.787051 0.250589 0.514612 0.029 Uiso 1 1 calc R U . . .
H10B H 0.860295 0.285290 0.429109 0.029 Uiso 1 1 calc R U . . .
C11 C 0.6188(3) 0.33768(12) 0.34193(15) 0.0240(4) Uani 1 1 d . . . . .
H11A H 0.591632 0.301194 0.298137 0.029 Uiso 1 1 calc R U . . .
H11B H 0.534890 0.370390 0.337659 0.029 Uiso 1 1 calc R U . . .
C12 C 0.7587(3) 0.36990(13) 0.31589(16) 0.0308(5) Uani 1 1 d . . . . .
C13 C 0.8749(3) 0.39566(15) 0.30086(17) 0.0400(7) Uani 1 1 d . . . . .
H13 H 0.968099 0.416323 0.288808 0.048 Uiso 1 1 calc R U . . .
C14 C 0.2202(3) 0.35575(12) 0.46538(16) 0.0258(5) Uani 1 1 d . . . . .
H14A H 0.269398 0.383144 0.419519 0.031 Uiso 1 1 calc R U . . .
H14B H 0.162587 0.319962 0.431771 0.031 Uiso 1 1 calc R U . . .
C15 C 0.1146(3) 0.39745(13) 0.51386(18) 0.0310(5) Uani 1 1 d . . . . .
C16 C 0.0349(3) 0.42956(15) 0.5578(2) 0.0395(6) Uani 1 1 d . . . . .
H16 H -0.029354 0.455436 0.593304 0.047 Uiso 1 1 calc R U . . .
C17 C 0.1874(2) 0.14757(11) 0.44791(16) 0.0245(4) Uani 1 1 d . . . . .
H17A H 0.129692 0.178428 0.405469 0.029 Uiso 1 1 calc R U . . .
H17B H 0.248693 0.118220 0.410555 0.029 Uiso 1 1 calc R U . . .
C18 C 0.0810(3) 0.10718(12) 0.49720(18) 0.0301(5) Uani 1 1 d . . . . .
C19 C 0.0010(3) 0.07633(14) 0.5431(2) 0.0393(6) Uani 1 1 d . . . . .
H19 H -0.063293 0.051559 0.579886 0.047 Uiso 1 1 calc R U . . .
C20 C 0.5287(2) 0.13171(12) 0.33382(15) 0.0242(4) Uani 1 1 d . . . . .
H20A H 0.435692 0.107750 0.348670 0.029 Uiso 1 1 calc R U . . .
H20B H 0.501226 0.162267 0.281883 0.029 Uiso 1 1 calc R U . . .
C21 C 0.6421(3) 0.08354(13) 0.30586(17) 0.0290(5) Uani 1 1 d . . . . .
C22 C 0.7388(3) 0.04717(14) 0.28592(19) 0.0379(6) Uani 1 1 d . . . . .
H22 H 0.816778 0.017820 0.269825 0.045 Uiso 1 1 calc R U . . .
Cl1A Cl 0.27399(19) 0.27407(12) 0.22883(15) 0.0131(5) Uani 0.6 1 d . . P A 1
O1A O 0.2987(11) 0.2475(5) 0.3231(6) 0.0209(13) Uani 0.6 1 d . . P A 1
O2A O 0.1401(8) 0.2465(4) 0.1843(5) 0.0313(13) Uani 0.6 1 d . . P A 1
O3A O 0.3952(6) 0.2447(3) 0.1776(3) 0.0305(10) Uani 0.6 1 d . . P A 1
O4A O 0.2742(6) 0.3440(2) 0.2239(3) 0.0321(9) Uani 0.6 1 d . . P A 1
Cl1B Cl 0.2614(5) 0.2730(2) 0.2307(3) 0.0496(16) Uani 0.4 1 d . . P A 2
O1B O 0.3095(18) 0.2577(7) 0.3243(12) 0.021(3) Uiso 0.4 1 d . . P A 2
O2B O 0.1256(15) 0.2414(6) 0.2002(8) 0.029(2) Uiso 0.4 1 d . . P A 2
O3B O 0.3957(11) 0.2632(4) 0.1749(7) 0.031(2) Uiso 0.4 1 d . . P A 2
O4B O 0.2311(8) 0.3441(5) 0.2342(6) 0.032(2) Uiso 0.4 1 d . . P A 2
Cl2 Cl 0.20814(5) 0.01194(2) 0.24407(3) 0.02157(12) Uani 1 1 d . . . . .
O5 O 0.3120(2) -0.01641(10) 0.18334(14) 0.0396(4) Uani 1 1 d . . . . .
O6 O 0.2025(2) 0.08281(9) 0.23067(13) 0.0391(5) Uani 1 1 d . . . . .
O7 O 0.2584(2) -0.00167(9) 0.33865(12) 0.0350(4) Uani 1 1 d . . . . .
O8 O 0.06030(18) -0.01646(9) 0.22309(13) 0.0344(4) 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 N1 2.0711(17) . ?
Cu1 N2 2.0959(18) . ?
Cu1 N3 2.0999(18) . ?
Cu1 N4 2.1274(17) . ?
Cu1 O1B 2.301(17) . ?
Cu1 O1A 2.359(9) . ?
N1 C10 1.492(3) . ?
N1 C1 1.502(3) . ?
N1 C11 1.507(3) . ?
N2 C4 1.495(3) . ?
N2 C3 1.497(3) . ?
N2 C14 1.509(3) . ?
N3 C6 1.499(3) . ?
N3 C17 1.503(3) . ?
N3 C5 1.505(3) . ?
N4 C9 1.500(3) . ?
N4 C8 1.501(3) . ?
N4 C20 1.509(3) . ?
C1 C2 1.503(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.503(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.480(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.512(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.516(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.499(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.469(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.185(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.473(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.178(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.469(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.183(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.473(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.177(4) . ?
C22 H22 0.9500 . ?
Cl1A O4A 1.409(5) . ?
Cl1A O2A 1.419(7) . ?
Cl1A O1A 1.472(9) . ?
Cl1A O3A 1.473(5) . ?
Cl1B O2B 1.400(14) . ?
Cl1B O1B 1.429(18) . ?
Cl1B O4B 1.457(10) . ?
Cl1B O3B 1.499(11) . ?
Cl2 O8 1.4371(17) . ?
Cl2 O5 1.4379(18) . ?
Cl2 O7 1.4397(17) . ?
Cl2 O6 1.4402(18) . ?

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 N2 93.87(7) . . ?
N1 Cu1 N3 167.92(7) . . ?
N2 Cu1 N3 84.87(7) . . ?
N1 Cu1 N4 85.06(7) . . ?
N2 Cu1 N4 169.55(7) . . ?
N3 Cu1 N4 94.00(7) . . ?
N1 Cu1 O1B 101.7(4) . . ?
N2 Cu1 O1B 97.0(4) . . ?
N3 Cu1 O1B 90.3(4) . . ?
N4 Cu1 O1B 93.4(4) . . ?
N1 Cu1 O1A 106.2(2) . . ?
N2 Cu1 O1A 99.4(2) . . ?
N3 Cu1 O1A 85.8(2) . . ?
N4 Cu1 O1A 90.8(2) . . ?
C10 N1 C1 105.99(16) . . ?
C10 N1 C11 110.81(17) . . ?
C1 N1 C11 108.88(17) . . ?
C10 N1 Cu1 103.17(13) . . ?
C1 N1 Cu1 117.80(13) . . ?
C11 N1 Cu1 109.94(12) . . ?
C4 N2 C3 105.32(18) . . ?
C4 N2 C14 111.90(18) . . ?
C3 N2 C14 108.86(17) . . ?
C4 N2 Cu1 102.47(13) . . ?
C3 N2 Cu1 119.05(14) . . ?
C14 N2 Cu1 109.06(13) . . ?
C6 N3 C17 109.96(17) . . ?
C6 N3 C5 108.73(17) . . ?
C17 N3 C5 106.04(17) . . ?
C6 N3 Cu1 105.65(13) . . ?
C17 N3 Cu1 119.28(13) . . ?
C5 N3 Cu1 106.82(14) . . ?
C9 N4 C8 108.08(16) . . ?
C9 N4 C20 106.51(16) . . ?
C8 N4 C20 109.93(17) . . ?
C9 N4 Cu1 106.25(13) . . ?
C8 N4 Cu1 107.33(13) . . ?
C20 N4 Cu1 118.31(12) . . ?
N1 C1 C2 114.17(18) . . ?
N1 C1 H1A 108.7 . . ?
C2 C1 H1A 108.7 . . ?
N1 C1 H1B 108.7 . . ?
C2 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
C1 C2 C3 111.0(2) . . ?
C1 C2 H2A 109.4 . . ?
C3 C2 H2A 109.4 . . ?
C1 C2 H2B 109.4 . . ?
C3 C2 H2B 109.4 . . ?
H2A C2 H2B 108.0 . . ?
N2 C3 C2 113.91(19) . . ?
N2 C3 H3A 108.8 . . ?
C2 C3 H3A 108.8 . . ?
N2 C3 H3B 108.8 . . ?
C2 C3 H3B 108.8 . . ?
H3A C3 H3B 107.7 . . ?
C5 C4 N2 109.86(19) . . ?
C5 C4 H4A 109.7 . . ?
N2 C4 H4A 109.7 . . ?
C5 C4 H4B 109.7 . . ?
N2 C4 H4B 109.7 . . ?
H4A C4 H4B 108.2 . . ?
C4 C5 N3 110.47(18) . . ?
C4 C5 H5A 109.6 . . ?
N3 C5 H5A 109.6 . . ?
C4 C5 H5B 109.6 . . ?
N3 C5 H5B 109.6 . . ?
H5A C5 H5B 108.1 . . ?
N3 C6 C7 115.27(18) . . ?
N3 C6 H6A 108.5 . . ?
C7 C6 H6A 108.5 . . ?
N3 C6 H6B 108.5 . . ?
C7 C6 H6B 108.5 . . ?
H6A C6 H6B 107.5 . . ?
C6 C7 C8 115.30(19) . . ?
C6 C7 H7A 108.4 . . ?
C8 C7 H7A 108.4 . . ?
C6 C7 H7B 108.4 . . ?
C8 C7 H7B 108.4 . . ?
H7A C7 H7B 107.5 . . ?
N4 C8 C7 114.65(17) . . ?
N4 C8 H8A 108.6 . . ?
C7 C8 H8A 108.6 . . ?
N4 C8 H8B 108.6 . . ?
C7 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
C10 C9 N4 110.03(17) . . ?
C10 C9 H9A 109.7 . . ?
N4 C9 H9A 109.7 . . ?
C10 C9 H9B 109.7 . . ?
N4 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
N1 C10 C9 109.99(17) . . ?
N1 C10 H10A 109.7 . . ?
C9 C10 H10A 109.7 . . ?
N1 C10 H10B 109.7 . . ?
C9 C10 H10B 109.7 . . ?
H10A C10 H10B 108.2 . . ?
C12 C11 N1 111.70(18) . . ?
C12 C11 H11A 109.3 . . ?
N1 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
N1 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C13 C12 C11 175.6(2) . . ?
C12 C13 H13 180.0 . . ?
C15 C14 N2 111.76(19) . . ?
C15 C14 H14A 109.3 . . ?
N2 C14 H14A 109.3 . . ?
C15 C14 H14B 109.3 . . ?
N2 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
C16 C15 C14 175.7(3) . . ?
C15 C16 H16 180.0 . . ?
C18 C17 N3 111.01(19) . . ?
C18 C17 H17A 109.4 . . ?
N3 C17 H17A 109.4 . . ?
C18 C17 H17B 109.4 . . ?
N3 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C19 C18 C17 174.9(3) . . ?
C18 C19 H19 180.0 . . ?
C21 C20 N4 111.33(18) . . ?
C21 C20 H20A 109.4 . . ?
N4 C20 H20A 109.4 . . ?
C21 C20 H20B 109.4 . . ?
N4 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
C22 C21 C20 176.4(3) . . ?
C21 C22 H22 180.0 . . ?
O4A Cl1A O2A 111.8(4) . . ?
O4A Cl1A O1A 114.2(4) . . ?
O2A Cl1A O1A 110.1(5) . . ?
O4A Cl1A O3A 111.8(3) . . ?
O2A Cl1A O3A 102.9(4) . . ?
O1A Cl1A O3A 105.2(5) . . ?
Cl1A O1A Cu1 145.9(6) . . ?
O2B Cl1B O1B 113.0(8) . . ?
O2B Cl1B O4B 107.5(7) . . ?
O1B Cl1B O4B 102.8(8) . . ?
O2B Cl1B O3B 117.5(7) . . ?
O1B Cl1B O3B 107.2(8) . . ?
O4B Cl1B O3B 107.6(5) . . ?
Cl1B O1B Cu1 162.1(10) . . ?
O8 Cl2 O5 108.83(11) . . ?
O8 Cl2 O7 109.75(11) . . ?
O5 Cl2 O7 110.22(12) . . ?
O8 Cl2 O6 110.09(11) . . ?
O5 Cl2 O6 109.09(12) . . ?
O7 Cl2 O6 108.83(11) . . ?

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
C10 N1 C1 C2 -168.34(19) . . . . ?
C11 N1 C1 C2 72.4(2) . . . . ?
Cu1 N1 C1 C2 -53.6(2) . . . . ?
N1 C1 C2 C3 74.9(2) . . . . ?
C4 N2 C3 C2 163.95(19) . . . . ?
C14 N2 C3 C2 -75.9(2) . . . . ?
Cu1 N2 C3 C2 49.9(2) . . . . ?
C1 C2 C3 N2 -72.2(2) . . . . ?
C3 N2 C4 C5 -175.63(18) . . . . ?
C14 N2 C4 C5 66.3(2) . . . . ?
Cu1 N2 C4 C5 -50.4(2) . . . . ?
N2 C4 C5 N3 55.0(2) . . . . ?
C6 N3 C5 C4 85.1(2) . . . . ?
C17 N3 C5 C4 -156.73(19) . . . . ?
Cu1 N3 C5 C4 -28.5(2) . . . . ?
C17 N3 C6 C7 63.6(2) . . . . ?
C5 N3 C6 C7 179.31(19) . . . . ?
Cu1 N3 C6 C7 -66.3(2) . . . . ?
N3 C6 C7 C8 69.8(2) . . . . ?
C9 N4 C8 C7 176.68(18) . . . . ?
C20 N4 C8 C7 -67.4(2) . . . . ?
Cu1 N4 C8 C7 62.5(2) . . . . ?
C6 C7 C8 N4 -66.9(3) . . . . ?
C8 N4 C9 C10 -86.0(2) . . . . ?
C20 N4 C9 C10 155.90(18) . . . . ?
Cu1 N4 C9 C10 28.9(2) . . . . ?
C1 N1 C10 C9 174.82(18) . . . . ?
C11 N1 C10 C9 -67.2(2) . . . . ?
Cu1 N1 C10 C9 50.41(19) . . . . ?
N4 C9 C10 N1 -55.2(2) . . . . ?
C10 N1 C11 C12 -55.9(2) . . . . ?
C1 N1 C11 C12 60.3(2) . . . . ?
Cu1 N1 C11 C12 -169.33(17) . . . . ?
C4 N2 C14 C15 54.2(3) . . . . ?
C3 N2 C14 C15 -61.8(2) . . . . ?
Cu1 N2 C14 C15 166.87(17) . . . . ?
C6 N3 C17 C18 58.9(2) . . . . ?
C5 N3 C17 C18 -58.5(2) . . . . ?
Cu1 N3 C17 C18 -178.88(15) . . . . ?
C9 N4 C20 C21 55.1(2) . . . . ?
C8 N4 C20 C21 -61.8(2) . . . . ?
Cu1 N4 C20 C21 174.50(16) . . . . ?
O4A Cl1A O1A Cu1 -50.9(11) . . . . ?
O2A Cl1A O1A Cu1 -177.7(9) . . . . ?
O3A Cl1A O1A Cu1 72.0(11) . . . . ?
O2B Cl1B O1B Cu1 171(3) . . . . ?
O4B Cl1B O1B Cu1 -73(3) . . . . ?
O3B Cl1B O1B Cu1 40(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C3 H3A O2A^a 0.99 2.63 3.431(7) 138.7 4_666 yes
C3 H3A O2B^b 0.99 2.55 3.399(13) 143.8 4_666 yes
C3 H3A O6 0.99 2.53 3.223(3) 126.7 4_666 yes
C4 H4A O2A^a 0.99 2.55 3.416(7) 145.6 4_666 yes
C4 H4A O2B^b 0.99 2.45 3.349(14) 150.4 4_666 yes
C5 H5B O3B^b 0.99 2.55 3.121(10) 116.5 4_566 yes
C6 H6B O2A^a 0.99 2.58 3.508(7) 156.0 4_666 yes
C6 H6B O2B^b 0.99 2.64 3.595(13) 161.0 4_666 yes
C7 H7B O7 0.99 2.49 3.363(3) 147.0 3_656 yes
C8 H8A O4A^a 0.99 2.64 3.512(5) 146.8 4_666 yes
C10 H10A O3A^a 0.99 2.49 3.433(5) 158.9 4_666 yes
C10 H10A O3B^b 0.99 2.47 3.434(10) 164.8 4_666 yes
C11 H11A Cl1A^a 0.99 2.96 3.588(3) 122.3 . yes
C11 H11A O3A^a 0.99 2.63 3.524(6) 150.0 . yes
C11 H11A O3B^b 0.99 2.52 3.365(10) 143.6 . yes
C11 H11B O8 0.99 2.56 3.434(3) 146.9 2 yes
C14 H14A O5 0.99 2.58 3.360(3) 135.1 2 yes
C14 H14B O1A^a 0.99 2.52 3.118(10) 118.6 . yes
C14 H14B O1B^b 0.99 2.45 2.995(16) 114.2 . yes
C17 H17A O1A^a 0.99 2.42 2.927(10) 111.1 . yes
C17 H17A O1B^b 0.99 2.60 3.097(15) 111.4 . yes
C17 H17B O7 0.99 2.63 3.477(3) 143.1 . yes
C20 H20A O6 0.99 2.63 3.298(3) 125.0 . yes
C20 H20B O1A^a 0.99 2.58 3.088(10) 111.8 . yes
C20 H20B O3A^a 0.99 2.39 3.365(6) 167.7 . yes

_refine_diff_density_max         0.707
_refine_diff_density_min         -0.396
_refine_diff_density_rms         0.072

####################################################################### 
# 
# 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_pjr13pt2_2_sx
_database_code_depnum_ccdc_archive 'CCDC 2012633'
loop_
_audit_author_name
_audit_author_address
'Peter Turner'
;University of Sydney
Australia
;
_audit_update_record             
;
2020-06-28 deposited with the CCDC.	2021-02-26 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         ?
_chemical_formula_sum            'C23 H38 Cl2 Cu N4 O10'
_chemical_formula_weight         665.01

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.4967(7)
_cell_length_b                   14.8226(11)
_cell_length_c                   21.4254(15)
_cell_angle_alpha                90
_cell_angle_beta                 100.8900(10)
_cell_angle_gamma                90
_cell_volume                     2961.7(4)
_cell_formula_units_Z            4

_cell_measurement_temperature    150.0(5)
_cell_measurement_reflns_used    9990
_cell_measurement_theta_min      2.58
_cell_measurement_theta_max      28.27

_exptl_crystal_description       blade
_exptl_crystal_colour            'dark blue'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_F_000             1388
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.219
_exptl_crystal_size_mid          0.182
_exptl_crystal_size_min          0.073
_exptl_absorpt_coefficient_mu    0.976
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6958
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
 SADABS (Sheldrick, 1996)
;

_diffrn_crystal_treatment        
;
attached with Exxon Paratone N, to a short length 
of fibre supported on a thin piece of copper wire 
inserted in a copper mounting pin.  The crystal was 
quenched in a cold nitrogen gas stream from an 
Oxford Cryosystems Cryostream. 
;

_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.0(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  APEXII-FR591
_diffrn_measurement_method       ω+φ
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            51703
_diffrn_reflns_av_unetI/netI     0.0213
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.936
_diffrn_reflns_theta_max         30.511
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.974
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             8828
_reflns_number_gt                6207
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'APEX (Bruker-AXS,2012)'
_computing_cell_refinement       'SAINT (Bruker-AXS,2012)'
_computing_data_reduction        'SAINT and XPREP (Bruker-AXS,2012)'
_computing_structure_solution    'SIR2011 (Burla, et. al. 2012)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
;
  OLEX2 (Dolomanov,O.V.et al., 2009)
  shelXle (Hübschle,C.B., et al., 2011) 
;

_computing_publication_material  
;    
  WinGX (Farrugia, 1999)
;

_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)+(0.04P)²+8.0P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8828
_refine_ls_number_parameters     368
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0961
_refine_ls_R_factor_gt           0.0715
_refine_ls_wR_factor_ref         0.1724
_refine_ls_wR_factor_gt          0.1594
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
Cu1 Cu 0.29295(4) 0.25078(3) 0.12074(2) 0.04371(13) Uani 1 1 d . . . . .
O1 O 0.0473(3) 0.18798(18) 0.13352(13) 0.0497(6) Uani 1 1 d . . . . .
N1 N 0.1763(4) 0.2358(2) 0.02900(15) 0.0514(7) Uani 1 1 d . . . . .
N2 N 0.2517(3) 0.3858(2) 0.12674(14) 0.0463(7) Uani 1 1 d . . . . .
N3 N 0.3967(4) 0.2605(3) 0.21556(16) 0.0589(9) Uani 1 1 d . . . . .
N4 N 0.3917(4) 0.1295(2) 0.10401(16) 0.0555(8) Uani 1 1 d . . . . .
C1 C 0.2016(5) 0.3109(3) -0.01389(19) 0.0575(10) Uani 1 1 d . . . . .
H1A H 0.143839 0.299695 -0.056714 0.069 Uiso 1 1 calc R U . . .
H1B H 0.303861 0.310429 -0.017718 0.069 Uiso 1 1 calc R U . . .
C2 C 0.1645(4) 0.4042(3) 0.00821(19) 0.0538(9) Uani 1 1 d . . . . .
H2A H 0.167468 0.447854 -0.026470 0.065 Uiso 1 1 calc R U . . .
H2B H 0.065031 0.402911 0.015987 0.065 Uiso 1 1 calc R U . . .
C3 C 0.2612(4) 0.4370(3) 0.06689(18) 0.0525(9) Uani 1 1 d . . . . .
H3A H 0.238774 0.501155 0.073328 0.063 Uiso 1 1 calc R U . . .
H3B H 0.361307 0.434043 0.060071 0.063 Uiso 1 1 calc R U . . .
C4 C 0.3730(5) 0.4184(3) 0.1766(2) 0.0615(11) Uani 1 1 d . . . . .
H4A H 0.355420 0.481481 0.188138 0.074 Uiso 1 1 calc R U . . .
H4B H 0.463589 0.416545 0.160102 0.074 Uiso 1 1 calc R U . . .
C5 C 0.3851(6) 0.3585(4) 0.2345(2) 0.0709(13) Uani 1 1 d . . . . .
H5A H 0.299706 0.366584 0.254172 0.085 Uiso 1 1 calc R U . . .
H5B H 0.470980 0.375601 0.266143 0.085 Uiso 1 1 calc R U . . .
C6 C 0.5512(5) 0.2395(4) 0.2221(2) 0.0818(17) Uani 1 1 d . . . . .
H6A H 0.599206 0.250345 0.266640 0.098 Uiso 1 1 calc R U . . .
H6B H 0.594102 0.280972 0.194669 0.098 Uiso 1 1 calc R U . . .
C7 C 0.5793(5) 0.1429(4) 0.2043(2) 0.0837(17) Uani 1 1 d . . . . .
H7A H 0.681218 0.128221 0.220910 0.100 Uiso 1 1 calc R U . . .
H7B H 0.520022 0.101912 0.225119 0.100 Uiso 1 1 calc R U . . .
C8 C 0.5470(5) 0.1254(4) 0.1333(2) 0.0752(15) Uani 1 1 d . . . . .
H8A H 0.599123 0.170327 0.112143 0.090 Uiso 1 1 calc R U . . .
H8B H 0.584121 0.064948 0.125168 0.090 Uiso 1 1 calc R U . . .
C9 C 0.3801(5) 0.1310(3) 0.0334(2) 0.0667(12) Uani 1 1 d . . . . .
H9A H 0.443318 0.178516 0.021443 0.080 Uiso 1 1 calc R U . . .
H9B H 0.410903 0.072190 0.018652 0.080 Uiso 1 1 calc R U . . .
C10 C 0.2279(6) 0.1494(3) 0.0027(2) 0.0663(12) Uani 1 1 d . . . . .
H10A H 0.166504 0.098433 0.010931 0.080 Uiso 1 1 calc R U . . .
H10B H 0.220590 0.155051 -0.043800 0.080 Uiso 1 1 calc R U . . .
C11 C 0.0191(4) 0.2261(3) 0.0255(2) 0.0528(9) Uani 1 1 d . . . . .
H11A H -0.022164 0.285837 0.032175 0.063 Uiso 1 1 calc R U . . .
H11B H -0.025556 0.204973 -0.017568 0.063 Uiso 1 1 calc R U . . .
C12 C -0.0164(4) 0.1616(3) 0.0734(2) 0.0555(9) Uani 1 1 d . . . . .
C13 C -0.0998(6) 0.0899(3) 0.0591(3) 0.0818(15) Uani 1 1 d . . . . .
H13A H -0.119757 0.051709 0.091986 0.098 Uiso 1 1 calc R U . . .
H13B H -0.139639 0.076631 0.015985 0.098 Uiso 1 1 calc R U . . .
C14 C -0.0104(5) 0.1474(3) 0.1844(2) 0.0686(12) Uani 1 1 d . . . . .
H14A H -0.115380 0.147295 0.173361 0.103 Uiso 1 1 calc R U . . .
H14B H 0.020510 0.181975 0.223534 0.103 Uiso 1 1 calc R U . . .
H14C H 0.024352 0.085176 0.190816 0.103 Uiso 1 1 calc R U . . .
C15 C 0.1097(4) 0.4021(3) 0.1457(2) 0.0532(9) Uani 1 1 d . . . . .
H15A H 0.032458 0.378018 0.112269 0.064 Uiso 1 1 calc R U . . .
H15B H 0.106672 0.368823 0.185510 0.064 Uiso 1 1 calc R U . . .
C16 C 0.0824(5) 0.4985(3) 0.15549(19) 0.0564(10) Uani 1 1 d . . . . .
C17 C 0.0599(7) 0.5748(4) 0.1621(2) 0.0816(16) Uani 1 1 d . . . . .
H17 H 0.041594 0.637051 0.167432 0.098 Uiso 1 1 calc R U . . .
C18 C 0.3264(5) 0.2038(3) 0.25851(19) 0.0599(10) Uani 1 1 d . . . . .
H18A H 0.302498 0.144554 0.237950 0.072 Uiso 1 1 calc R U . . .
H18B H 0.235199 0.233033 0.263129 0.072 Uiso 1 1 calc R U . . .
C19 C 0.4138(6) 0.1883(4) 0.3233(2) 0.0721(13) Uani 1 1 d . . . . .
C20 C 0.4789(7) 0.1671(4) 0.3727(3) 0.0911(18) Uani 1 1 d . . . . .
H20 H 0.532007 0.149742 0.413002 0.109 Uiso 1 1 calc R U . . .
C21 C 0.3148(5) 0.0487(3) 0.1240(2) 0.0639(12) Uani 1 1 d . . . . .
H21A H 0.328337 0.047939 0.170935 0.077 Uiso 1 1 calc R U . . .
H21B H 0.210833 0.055300 0.107035 0.077 Uiso 1 1 calc R U . . .
C22 C 0.3637(7) -0.0386(4) 0.1022(3) 0.0848(18) Uani 1 1 d . . . . .
C23 C 0.3961(11) -0.1085(5) 0.0861(4) 0.156(4) Uani 1 1 d . . . . .
H23 H 0.422814 -0.166143 0.072764 0.187 Uiso 1 1 calc R U . . .
Cl1 Cl 0.67971(10) 0.36757(8) 0.06499(5) 0.0572(3) Uani 1 1 d . . . . .
O2 O 0.5493(4) 0.3184(3) 0.0546(2) 0.1033(14) Uani 1 1 d . . . . .
O3 O 0.7416(5) 0.3684(3) 0.01054(18) 0.1012(14) Uani 1 1 d . . . . .
O4 O 0.7768(3) 0.3259(3) 0.11613(16) 0.0796(10) Uani 1 1 d . . . . .
O5 O 0.6537(4) 0.4575(3) 0.08252(19) 0.0860(11) Uani 1 1 d . . . . .
Cl2 Cl 0.0058(2) 0.35834(9) 0.32530(5) 0.0873(5) Uani 1 1 d . . . . .
O6 O 0.1314(9) 0.4192(5) 0.3239(4) 0.197(4) Uani 1 1 d . . . . .
O7 O 0.0840(8) 0.2794(4) 0.3406(3) 0.157(3) Uani 1 1 d . . . . .
O8 O -0.0480(6) 0.3970(4) 0.3715(3) 0.138(2) Uani 1 1 d . . . . .
O9 O -0.0634(8) 0.3519(6) 0.2656(2) 0.185(3) Uani 1 1 d . . . . .
O1W O -0.2980(4) 0.4860(3) 0.22757(18) 0.0838(11) Uani 1 1 d D . . . .
H1WA H -0.229(6) 0.454(4) 0.251(3) 0.126 Uiso 1 1 d D U . . .
H1WB H -0.300(8) 0.503(5) 0.1885(15) 0.126 Uiso 1 1 d D 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
Cu1 N2 2.048(3) . ?
Cu1 N1 2.078(3) . ?
Cu1 N3 2.089(3) . ?
Cu1 N4 2.089(3) . ?
Cu1 O1 2.574(2) . ?
Cu1 O2 3.200(4) . ?
O1 C12 1.373(5) . ?
O1 C14 1.441(5) . ?
N1 C1 1.492(5) . ?
N1 C11 1.488(5) . ?
N1 C10 1.517(5) . ?
N2 C4 1.495(5) . ?
N2 C15 1.501(5) . ?
N2 C3 1.507(5) . ?
N3 C6 1.480(6) . ?
N3 C18 1.493(5) . ?
N3 C5 1.517(6) . ?
N4 C8 1.491(5) . ?
N4 C9 1.496(5) . ?
N4 C21 1.506(5) . ?
C1 C2 1.524(6) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.491(5) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.512(6) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.519(8) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.516(7) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.495(7) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.487(6) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.327(6) . ?
C13 H13A 0.9500 . ?
C13 H13B 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.474(6) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.164(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.494(6) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.163(7) . ?
C20 H20 0.9500 . ?
C21 C22 1.479(6) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.153(9) . ?
C23 H23 0.9500 . ?
Cl1 O3 1.402(4) . ?
Cl1 O5 1.419(4) . ?
Cl1 O2 1.418(4) . ?
Cl1 O4 1.432(3) . ?
Cl2 O9 1.327(6) . ?
Cl2 O8 1.328(4) . ?
Cl2 O7 1.391(5) . ?
Cl2 O6 1.500(7) . ?
O1W H1WA 0.88(2) . ?
O1W H1WB 0.87(2) . ?

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 95.16(13) . . ?
N2 Cu1 N3 86.09(14) . . ?
N1 Cu1 N3 175.37(13) . . ?
N2 Cu1 N4 161.59(12) . . ?
N1 Cu1 N4 85.52(13) . . ?
N3 Cu1 N4 94.70(15) . . ?
N2 Cu1 O1 99.14(10) . . ?
N1 Cu1 O1 74.34(11) . . ?
N3 Cu1 O1 101.07(11) . . ?
N4 Cu1 O1 98.75(11) . . ?
N2 Cu1 O2 83.82(12) . . ?
N1 Cu1 O2 85.92(12) . . ?
N3 Cu1 O2 98.65(12) . . ?
N4 Cu1 O2 77.88(12) . . ?
O1 Cu1 O2 160.21(10) . . ?
C12 O1 C14 115.3(3) . . ?
C12 O1 Cu1 104.5(2) . . ?
C14 O1 Cu1 135.5(3) . . ?
C1 N1 C11 108.5(3) . . ?
C1 N1 C10 107.5(3) . . ?
C11 N1 C10 106.9(3) . . ?
C1 N1 Cu1 112.6(3) . . ?
C11 N1 Cu1 114.1(2) . . ?
C10 N1 Cu1 106.8(3) . . ?
C4 N2 C15 111.4(3) . . ?
C4 N2 C3 106.5(3) . . ?
C15 N2 C3 110.5(3) . . ?
C4 N2 Cu1 103.3(3) . . ?
C15 N2 Cu1 111.5(2) . . ?
C3 N2 Cu1 113.3(2) . . ?
C6 N3 C18 111.9(3) . . ?
C6 N3 C5 107.3(4) . . ?
C18 N3 C5 108.1(4) . . ?
C6 N3 Cu1 110.8(3) . . ?
C18 N3 Cu1 112.1(3) . . ?
C5 N3 Cu1 106.4(3) . . ?
C8 N4 C9 107.7(3) . . ?
C8 N4 C21 110.0(3) . . ?
C9 N4 C21 110.6(4) . . ?
C8 N4 Cu1 113.8(3) . . ?
C9 N4 Cu1 102.2(2) . . ?
C21 N4 Cu1 112.2(2) . . ?
N1 C1 C2 114.3(3) . . ?
N1 C1 H1A 108.7 . . ?
C2 C1 H1A 108.7 . . ?
N1 C1 H1B 108.7 . . ?
C2 C1 H1B 108.7 . . ?
H1A C1 H1B 107.6 . . ?
C3 C2 C1 114.6(3) . . ?
C3 C2 H2A 108.6 . . ?
C1 C2 H2A 108.6 . . ?
C3 C2 H2B 108.6 . . ?
C1 C2 H2B 108.6 . . ?
H2A C2 H2B 107.6 . . ?
C2 C3 N2 115.3(3) . . ?
C2 C3 H3A 108.5 . . ?
N2 C3 H3A 108.5 . . ?
C2 C3 H3B 108.5 . . ?
N2 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
N2 C4 C5 109.0(3) . . ?
N2 C4 H4A 109.9 . . ?
C5 C4 H4A 109.9 . . ?
N2 C4 H4B 109.9 . . ?
C5 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
C4 C5 N3 109.9(4) . . ?
C4 C5 H5A 109.7 . . ?
N3 C5 H5A 109.7 . . ?
C4 C5 H5B 109.7 . . ?
N3 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
N3 C6 C7 113.2(4) . . ?
N3 C6 H6A 108.9 . . ?
C7 C6 H6A 108.9 . . ?
N3 C6 H6B 108.9 . . ?
C7 C6 H6B 108.9 . . ?
H6A C6 H6B 107.8 . . ?
C8 C7 C6 113.7(4) . . ?
C8 C7 H7A 108.8 . . ?
C6 C7 H7A 108.8 . . ?
C8 C7 H7B 108.8 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
N4 C8 C7 114.4(4) . . ?
N4 C8 H8A 108.7 . . ?
C7 C8 H8A 108.7 . . ?
N4 C8 H8B 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C10 C9 N4 109.1(3) . . ?
C10 C9 H9A 109.9 . . ?
N4 C9 H9A 109.9 . . ?
C10 C9 H9B 109.9 . . ?
N4 C9 H9B 109.9 . . ?
H9A C9 H9B 108.3 . . ?
C9 C10 N1 110.1(4) . . ?
C9 C10 H10A 109.6 . . ?
N1 C10 H10A 109.6 . . ?
C9 C10 H10B 109.6 . . ?
N1 C10 H10B 109.6 . . ?
H10A C10 H10B 108.1 . . ?
C12 C11 N1 112.5(3) . . ?
C12 C11 H11A 109.1 . . ?
N1 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
N1 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C13 C12 O1 125.6(5) . . ?
C13 C12 C11 124.0(5) . . ?
O1 C12 C11 110.4(3) . . ?
C12 C13 H13A 120.0 . . ?
C12 C13 H13B 120.0 . . ?
H13A C13 H13B 120.0 . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 N2 112.7(3) . . ?
C16 C15 H15A 109.0 . . ?
N2 C15 H15A 109.0 . . ?
C16 C15 H15B 109.0 . . ?
N2 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C17 C16 C15 178.8(5) . . ?
C16 C17 H17 180.0 . . ?
N3 C18 C19 115.1(4) . . ?
N3 C18 H18A 108.5 . . ?
C19 C18 H18A 108.5 . . ?
N3 C18 H18B 108.5 . . ?
C19 C18 H18B 108.5 . . ?
H18A C18 H18B 107.5 . . ?
C20 C19 C18 173.1(6) . . ?
C19 C20 H20 180.0 . . ?
C22 C21 N4 114.1(3) . . ?
C22 C21 H21A 108.7 . . ?
N4 C21 H21A 108.7 . . ?
C22 C21 H21B 108.7 . . ?
N4 C21 H21B 108.7 . . ?
H21A C21 H21B 107.6 . . ?
C23 C22 C21 176.7(7) . . ?
C22 C23 H23 180.0 . . ?
O3 Cl1 O5 109.4(2) . . ?
O3 Cl1 O2 111.4(3) . . ?
O5 Cl1 O2 109.5(2) . . ?
O3 Cl1 O4 109.3(2) . . ?
O5 Cl1 O4 108.8(2) . . ?
O2 Cl1 O4 108.4(2) . . ?
Cl1 O2 Cu1 143.8(3) . . ?
O9 Cl2 O8 124.1(4) . . ?
O9 Cl2 O7 108.1(4) . . ?
O8 Cl2 O7 116.8(4) . . ?
O9 Cl2 O6 106.0(5) . . ?
O8 Cl2 O6 100.1(4) . . ?
O7 Cl2 O6 96.8(5) . . ?
H1WA O1W H1WB 125(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
C11 N1 C1 C2 68.5(4) . . . . ?
C10 N1 C1 C2 -176.2(4) . . . . ?
Cu1 N1 C1 C2 -58.8(4) . . . . ?
N1 C1 C2 C3 68.6(5) . . . . ?
C1 C2 C3 N2 -67.4(5) . . . . ?
C4 N2 C3 C2 170.4(4) . . . . ?
C15 N2 C3 C2 -68.5(4) . . . . ?
Cu1 N2 C3 C2 57.5(4) . . . . ?
C15 N2 C4 C5 69.2(5) . . . . ?
C3 N2 C4 C5 -170.3(4) . . . . ?
Cu1 N2 C4 C5 -50.7(4) . . . . ?
N2 C4 C5 N3 53.7(5) . . . . ?
C6 N3 C5 C4 91.3(4) . . . . ?
C18 N3 C5 C4 -147.8(4) . . . . ?
Cu1 N3 C5 C4 -27.2(4) . . . . ?
C18 N3 C6 C7 61.9(5) . . . . ?
C5 N3 C6 C7 -179.7(4) . . . . ?
Cu1 N3 C6 C7 -64.1(4) . . . . ?
N3 C6 C7 C8 74.4(5) . . . . ?
C9 N4 C8 C7 167.9(4) . . . . ?
C21 N4 C8 C7 -71.4(6) . . . . ?
Cu1 N4 C8 C7 55.4(5) . . . . ?
C6 C7 C8 N4 -68.5(6) . . . . ?
C8 N4 C9 C10 -171.4(4) . . . . ?
C21 N4 C9 C10 68.4(4) . . . . ?
Cu1 N4 C9 C10 -51.2(4) . . . . ?
N4 C9 C10 N1 55.1(5) . . . . ?
C1 N1 C10 C9 93.1(4) . . . . ?
C11 N1 C10 C9 -150.5(4) . . . . ?
Cu1 N1 C10 C9 -28.0(4) . . . . ?
C1 N1 C11 C12 -171.9(3) . . . . ?
C10 N1 C11 C12 72.5(4) . . . . ?
Cu1 N1 C11 C12 -45.4(4) . . . . ?
C14 O1 C12 C13 -16.2(6) . . . . ?
Cu1 O1 C12 C13 143.5(4) . . . . ?
C14 O1 C12 C11 162.9(3) . . . . ?
Cu1 O1 C12 C11 -37.4(3) . . . . ?
N1 C11 C12 C13 -123.7(5) . . . . ?
N1 C11 C12 O1 57.2(4) . . . . ?
C4 N2 C15 C16 60.5(5) . . . . ?
C3 N2 C15 C16 -57.6(4) . . . . ?
Cu1 N2 C15 C16 175.3(3) . . . . ?
C6 N3 C18 C19 39.8(6) . . . . ?
C5 N3 C18 C19 -78.1(5) . . . . ?
Cu1 N3 C18 C19 165.0(3) . . . . ?
C8 N4 C21 C22 -63.2(5) . . . . ?
C9 N4 C21 C22 55.7(5) . . . . ?
Cu1 N4 C21 C22 169.1(4) . . . . ?
O3 Cl1 O2 Cu1 178.6(3) . . . . ?
O5 Cl1 O2 Cu1 -60.2(4) . . . . ?
O4 Cl1 O2 Cu1 58.4(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1A O7 0.99 2.46 3.384(7) 154.4 4_565 yes
C1 H1B O2 0.99 2.55 3.352(6) 138.5 . yes
C2 H2A O5 0.99 2.66 3.498(5) 142.7 3_665 yes
C3 H3B O2 0.99 2.49 3.304(6) 138.9 . yes
C4 H4B O1W 0.99 2.65 3.266(6) 120.3 1_655 yes
C5 H5A O6 0.99 2.51 3.469(8) 163.1 . yes
C8 H8A O2 0.99 2.52 3.323(7) 138.3 . yes
C9 H9A O2 0.99 2.35 3.198(7) 142.5 . yes
C11 H11A O3 0.99 2.52 3.344(6) 140.4 1_455 yes
C15 H15A O4 0.99 2.56 3.304(5) 131.4 1_455 yes
C15 H15B O9 0.99 2.58 3.383(8) 138.1 . yes
C18 H18A O1W 0.99 2.47 3.259(7) 136.7 2_545 yes
C18 H18B O7 0.99 2.49 3.343(8) 144.5 . yes
C21 H21A O1W 0.99 2.43 3.347(6) 154.2 2_545 yes
C21 H21B O1 0.99 2.63 3.309(5) 125.6 . yes
O1W H1WA Cl2 0.88(2) 2.86(2) 3.743(4) 176(6) . yes
O1W H1WA O9 0.88(2) 2.16(4) 2.982(8) 154(6) . yes
O1W H1WB O5 0.87(2) 2.33(5) 3.084(5) 145(6) 1_455 yes

_refine_diff_density_max         1.209
_refine_diff_density_min         -0.693
_refine_diff_density_rms         0.093

####################################################################### 
# 
# 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_pjr14ajc_s004
_database_code_depnum_ccdc_archive 'CCDC 2012629'
loop_
_audit_author_name
_audit_author_address
'Peter Turner'
;University of Sydney
Australia
;
_audit_update_record             
;
2020-06-28 deposited with the CCDC.	2021-02-26 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         ?
_chemical_formula_sum            'C22 H34 Cl2 Cu N4 O10'
_chemical_formula_weight         648.97

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.15300(10)
_cell_length_b                   17.56480(10)
_cell_length_c                   19.34900(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.9230(10)
_cell_angle_gamma                90
_cell_volume                     2750.69(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150.0(5)
_cell_measurement_reflns_used    60200
_cell_measurement_theta_max      75.8300
_cell_measurement_theta_min      3.3900

_exptl_crystal_description       prism
_exptl_crystal_colour            'translucent dark blue'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_F_000             1348
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.427
_exptl_crystal_size_mid          0.302
_exptl_crystal_size_min          0.225
_exptl_absorpt_coefficient_mu    3.444
_shelx_estimated_absorpt_T_min   0.321
_shelx_estimated_absorpt_T_max   0.511
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55033
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 CrysAlisPro, Agilent Technologies, Version 1.171.37.33 
 (compiled Mar 27 2014,17:12:48) 
 Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_crystal_treatment        
;
attached with Exxon Paratone N, to a short length 
of fibre supported on a thin piece of copper wire 
inserted in a copper mounting pin.  The crystal was 
quenched in a cold nitrogen gas stream from an 
Oxford Cryosystems Cryostream. 
;

_diffrn_ambient_temperature      150.0(5)
_diffrn_ambient_environment      N~2~
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_device       'κ-geometry four circle diffractometer'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.5861
_diffrn_measurement_method       ω

_diffrn_reflns_number            97600
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_av_R_equivalents  0.0687
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.410
_diffrn_reflns_theta_max         76.011
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5732
_reflns_number_gt                5412
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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_cell_refinement       
;
 CrysAlisPro, Agilent Technologies, Version 1.171.37.33 
 (compiled Mar 27 2014,17:12:48)
;
_computing_data_collection       
;
 CrysAlisPro, Agilent Technologies, Version 1.171.37.33 
 (compiled Mar 27 2014,17:12:48)
;
_computing_data_reduction        
;
 CrysAlisPro, Agilent Technologies, Version 1.171.37.33 
 (compiled Mar 27 2014,17:12:48)
;
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_molecular_graphics    
;
  OLEX2 (Dolomanov,O.V.et al., 2009)
  shelXle (Hübschle,C.B., et al., 2011) 
;

_computing_publication_material  
;    
  WinGX (Farrugia, 1999)
;


_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)+(0.04P)²+2.0P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5732
_refine_ls_number_parameters     397
_refine_ls_number_restraints     346
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1076
_refine_ls_wR_factor_gt          0.1064
_refine_ls_goodness_of_fit_ref   1.365
_refine_ls_restrained_S_all      1.332
_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 0.27917(3) 0.25509(2) 0.39436(2) 0.01815(10) Uani 1 1 d . . . . .
O1 O 0.4053(2) 0.28434(9) 0.30074(8) 0.0272(3) Uani 1 1 d . . . . .
O2 O 0.4476(2) 0.38505(10) 0.23383(8) 0.0350(4) Uani 1 1 d . . . . .
N1 N 0.1686(3) 0.36012(11) 0.36367(10) 0.0304(4) Uani 1 1 d . . . . .
N2 N 0.0630(2) 0.20498(11) 0.35019(10) 0.0256(4) Uani 1 1 d . . . . .
N3 N 0.4016(2) 0.15284(10) 0.41972(9) 0.0234(4) Uani 1 1 d . . . . .
N4 N 0.4354(2) 0.30215(10) 0.47414(9) 0.0210(3) Uani 1 1 d . . . . .
C1 C 0.0057(3) 0.33834(16) 0.32260(15) 0.0428(6) Uani 1 1 d . . . . .
H1A H -0.074793 0.380367 0.323972 0.051 Uiso 1 1 calc R U . . .
H1B H 0.021416 0.328885 0.273395 0.051 Uiso 1 1 calc R U . . .
C2 C -0.0592(3) 0.26726(17) 0.35401(15) 0.0400(6) Uani 1 1 d . . . . .
H2A H -0.075756 0.276765 0.403117 0.048 Uiso 1 1 calc R U . . .
H2B H -0.166688 0.252661 0.328082 0.048 Uiso 1 1 calc R U . . .
C3 C 0.0141(3) 0.14012(16) 0.39348(13) 0.0359(5) Uani 1 1 d . . . . .
H3A H -0.092739 0.119612 0.371520 0.043 Uiso 1 1 calc R U . . .
H3B H -0.003609 0.160020 0.439872 0.043 Uiso 1 1 calc R U . . .
C4 C 0.1366(3) 0.07564(15) 0.40341(14) 0.0383(6) Uani 1 1 d . . . . .
H4A H 0.164991 0.059607 0.357262 0.046 Uiso 1 1 calc R U . . .
H4B H 0.083745 0.031798 0.424077 0.046 Uiso 1 1 calc R U . . .
C5 C 0.2944(3) 0.09554(13) 0.44947(12) 0.0312(5) Uani 1 1 d . . . . .
H5A H 0.264860 0.115243 0.494288 0.037 Uiso 1 1 calc R U . . .
H5B H 0.359132 0.048309 0.459525 0.037 Uiso 1 1 calc R U . . .
C6 C 0.5399(3) 0.17214(13) 0.47570(12) 0.0284(5) Uani 1 1 d . . . . .
H6A H 0.638894 0.187739 0.454210 0.034 Uiso 1 1 calc R U . . .
H6B H 0.568959 0.126798 0.505035 0.034 Uiso 1 1 calc R U . . .
C7 C 0.4864(3) 0.23639(13) 0.52027(12) 0.0262(4) Uani 1 1 d . . . . .
H7A H 0.392816 0.219644 0.544767 0.031 Uiso 1 1 calc R U . . .
H7B H 0.578868 0.251347 0.555577 0.031 Uiso 1 1 calc R U . . .
C8 C 0.3530(3) 0.35911(13) 0.51603(12) 0.0281(5) Uani 1 1 d . . . . .
H8A H 0.435026 0.377521 0.554294 0.034 Uiso 1 1 calc R U . . .
H8B H 0.264091 0.333035 0.537462 0.034 Uiso 1 1 calc R U . . .
C9 C 0.2793(3) 0.42738(14) 0.47570(13) 0.0333(5) Uani 1 1 d . . . . .
H9A H 0.365949 0.451144 0.451118 0.040 Uiso 1 1 calc R U . . .
H9B H 0.245447 0.465234 0.509135 0.040 Uiso 1 1 calc R U . . .
C10 C 0.1314(3) 0.40923(15) 0.42285(14) 0.0367(6) Uani 1 1 d . . . . .
H10A H 0.046767 0.383518 0.447166 0.044 Uiso 1 1 calc R U . . .
H10B H 0.083224 0.457680 0.403750 0.044 Uiso 1 1 calc R U . . .
C11 C 0.2667(3) 0.40253(14) 0.31700(12) 0.0332(5) Uani 1 1 d . . . . .
H11A H 0.334046 0.441639 0.344186 0.040 Uiso 1 1 calc R U . . .
H11B H 0.191199 0.428905 0.280817 0.040 Uiso 1 1 calc R U . . .
C12 C 0.3788(3) 0.35017(13) 0.28256(11) 0.0271(4) Uani 1 1 d . . . . .
C13 C 0.5652(4) 0.34190(18) 0.19901(14) 0.0444(6) Uani 1 1 d . . . . .
H13A H 0.607957 0.373962 0.163792 0.067 Uiso 1 1 calc R U . . .
H13B H 0.656757 0.325406 0.233212 0.067 Uiso 1 1 calc R U . . .
H13C H 0.510258 0.297176 0.176488 0.067 Uiso 1 1 calc R U . . .
C14 C 0.0633(3) 0.17918(15) 0.27610(12) 0.0292(5) Uani 1 1 d . . . . .
H14A H 0.097787 0.222050 0.247942 0.035 Uiso 1 1 calc R U . . .
H14B H 0.144841 0.137655 0.274573 0.035 Uiso 1 1 calc R U . . .
C15 C -0.0999(3) 0.15210(16) 0.24554(12) 0.0342(5) Uani 1 1 d . . . . .
C16 C -0.2322(3) 0.13018(19) 0.22295(14) 0.0454(7) Uani 1 1 d . . . . .
H16 H -0.338834 0.112503 0.204733 0.054 Uiso 1 1 calc R U . . .
C17 C 0.4746(3) 0.12182(13) 0.35831(11) 0.0263(4) Uani 1 1 d . . . . .
H17A H 0.383889 0.107150 0.322084 0.032 Uiso 1 1 calc R U . . .
H17B H 0.539227 0.162526 0.338730 0.032 Uiso 1 1 calc R U . . .
C18 C 0.5821(3) 0.05576(13) 0.37457(11) 0.0260(4) Uani 1 1 d . . . . .
C19 C 0.6722(3) 0.00341(14) 0.38489(13) 0.0340(5) Uani 1 1 d . . . . .
H19 H 0.744865 -0.038764 0.393201 0.041 Uiso 1 1 calc R U . . .
C20 C 0.5812(3) 0.33749(14) 0.44692(12) 0.0270(4) Uani 1 1 d . . . . .
H20A H 0.626302 0.301175 0.414925 0.032 Uiso 1 1 calc R U . . .
H20B H 0.544551 0.383470 0.419749 0.032 Uiso 1 1 calc R U . . .
C21 C 0.7136(3) 0.35900(13) 0.50217(12) 0.0289(5) Uani 1 1 d . . . . .
C22 C 0.8195(3) 0.37434(15) 0.54670(14) 0.0360(5) Uani 1 1 d . . . . .
H22 H 0.905086 0.386742 0.582703 0.043 Uiso 1 1 calc R U . . .
Cl1 Cl 0.01330(7) 0.17684(3) 0.59739(3) 0.03166(14) Uani 1 1 d . . . . .
O3 O 0.0625(3) 0.23074(12) 0.54728(13) 0.0532(6) Uani 1 1 d . . . . .
O4 O 0.1468(4) 0.1691(2) 0.65098(17) 0.1052(12) Uani 1 1 d . . . . .
O5 O -0.1261(4) 0.20314(18) 0.62509(18) 0.0871(11) Uani 1 1 d . . . . .
O6 O -0.0115(4) 0.10521(14) 0.56381(14) 0.0753(8) Uani 1 1 d . . . . .
Cl2A Cl 0.2831(8) 0.0357(6) 0.1772(5) 0.0288(11) Uani 0.5 1 d . . P A 1
O7A O 0.3681(7) 0.1066(3) 0.1917(3) 0.0493(13) Uani 0.5 1 d . . P A 1
O8A O 0.1438(17) 0.0515(9) 0.1269(8) 0.063(4) Uani 0.5 1 d . . P A 1
O9A O 0.245(2) 0.0045(9) 0.2336(8) 0.065(4) Uani 0.5 1 d . . P A 1
O10A O 0.3994(10) -0.0066(5) 0.1395(3) 0.083(2) Uani 0.5 1 d . . P A 1
Cl2B Cl 0.2772(10) 0.0240(6) 0.1732(5) 0.0335(15) Uani 0.5 1 d . . P B 2
O7B O 0.4229(9) 0.0637(5) 0.1884(4) 0.095(3) Uani 0.5 1 d . . P B 2
O8B O 0.1500(15) 0.0686(8) 0.1367(6) 0.048(3) Uani 0.5 1 d . . P B 2
O9B O 0.2244(17) 0.0008(5) 0.2439(6) 0.0355(16) Uani 0.5 1 d . . P B 2
O10B O 0.3019(8) -0.0427(4) 0.1401(3) 0.0627(15) Uani 0.5 1 d . . P B 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N4 2.0529(17) . ?
Cu1 N2 2.0615(18) . ?
Cu1 N3 2.0844(18) . ?
Cu1 N1 2.1071(19) . ?
Cu1 O1 2.2477(15) . ?
Cu1 O3 3.649(2) . ?
O1 C12 1.220(3) . ?
O2 C12 1.306(3) . ?
O2 C13 1.450(3) . ?
N1 C11 1.478(3) . ?
N1 C10 1.494(3) . ?
N1 C1 1.512(3) . ?
N2 C2 1.487(3) . ?
N2 C3 1.496(3) . ?
N2 C14 1.504(3) . ?
N3 C5 1.493(3) . ?
N3 C17 1.495(3) . ?
N3 C6 1.505(3) . ?
N4 C7 1.488(3) . ?
N4 C20 1.492(3) . ?
N4 C8 1.497(3) . ?
C1 C2 1.511(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.507(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.515(4) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.516(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.515(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.518(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.507(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.468(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.179(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.465(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.179(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.474(3) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 C22 1.175(4) . ?
C22 H22 0.9500 . ?
Cl1 O5 1.393(2) . ?
Cl1 O4 1.416(3) . ?
Cl1 O6 1.419(2) . ?
Cl1 O3 1.446(2) . ?
Cl2A O9A 1.290(16) . ?
Cl2A O8A 1.432(16) . ?
Cl2A O7A 1.437(12) . ?
Cl2A O10A 1.467(9) . ?
Cl2B O10B 1.362(11) . ?
Cl2B O7B 1.378(11) . ?
Cl2B O8B 1.418(14) . ?
Cl2B O9B 1.537(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N4 Cu1 N2 154.93(7) . . ?
N4 Cu1 N3 86.21(7) . . ?
N2 Cu1 N3 95.21(8) . . ?
N4 Cu1 N1 93.73(7) . . ?
N2 Cu1 N1 86.65(8) . . ?
N3 Cu1 N1 175.74(8) . . ?
N4 Cu1 O1 102.19(6) . . ?
N2 Cu1 O1 102.41(7) . . ?
N3 Cu1 O1 97.70(6) . . ?
N1 Cu1 O1 78.14(7) . . ?
N4 Cu1 O3 75.80(6) . . ?
N2 Cu1 O3 79.21(7) . . ?
N3 Cu1 O3 88.45(6) . . ?
N1 Cu1 O3 95.66(7) . . ?
O1 Cu1 O3 173.42(5) . . ?
C12 O1 Cu1 111.52(15) . . ?
C12 O2 C13 117.1(2) . . ?
C11 N1 C10 110.6(2) . . ?
C11 N1 C1 108.2(2) . . ?
C10 N1 C1 107.60(19) . . ?
C11 N1 Cu1 111.63(14) . . ?
C10 N1 Cu1 114.14(15) . . ?
C1 N1 Cu1 104.21(15) . . ?
C2 N2 C3 107.91(19) . . ?
C2 N2 C14 110.31(19) . . ?
C3 N2 C14 109.60(18) . . ?
C2 N2 Cu1 102.09(14) . . ?
C3 N2 Cu1 111.41(14) . . ?
C14 N2 Cu1 115.11(13) . . ?
C5 N3 C17 111.63(17) . . ?
C5 N3 C6 107.29(17) . . ?
C17 N3 C6 108.57(17) . . ?
C5 N3 Cu1 112.68(14) . . ?
C17 N3 Cu1 110.63(13) . . ?
C6 N3 Cu1 105.74(13) . . ?
C7 N4 C20 110.97(17) . . ?
C7 N4 C8 107.76(16) . . ?
C20 N4 C8 109.98(17) . . ?
C7 N4 Cu1 103.98(13) . . ?
C20 N4 Cu1 110.53(13) . . ?
C8 N4 Cu1 113.46(13) . . ?
C2 C1 N1 109.0(2) . . ?
C2 C1 H1A 109.9 . . ?
N1 C1 H1A 109.9 . . ?
C2 C1 H1B 109.9 . . ?
N1 C1 H1B 109.9 . . ?
H1A C1 H1B 108.3 . . ?
N2 C2 C1 108.6(2) . . ?
N2 C2 H2A 110.0 . . ?
C1 C2 H2A 110.0 . . ?
N2 C2 H2B 110.0 . . ?
C1 C2 H2B 110.0 . . ?
H2A C2 H2B 108.3 . . ?
N2 C3 C4 115.3(2) . . ?
N2 C3 H3A 108.5 . . ?
C4 C3 H3A 108.5 . . ?
N2 C3 H3B 108.5 . . ?
C4 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
C3 C4 C5 113.8(2) . . ?
C3 C4 H4A 108.8 . . ?
C5 C4 H4A 108.8 . . ?
C3 C4 H4B 108.8 . . ?
C5 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
N3 C5 C4 115.08(19) . . ?
N3 C5 H5A 108.5 . . ?
C4 C5 H5A 108.5 . . ?
N3 C5 H5B 108.5 . . ?
C4 C5 H5B 108.5 . . ?
H5A C5 H5B 107.5 . . ?
N3 C6 C7 109.57(18) . . ?
N3 C6 H6A 109.8 . . ?
C7 C6 H6A 109.8 . . ?
N3 C6 H6B 109.8 . . ?
C7 C6 H6B 109.8 . . ?
H6A C6 H6B 108.2 . . ?
N4 C7 C6 108.38(17) . . ?
N4 C7 H7A 110.0 . . ?
C6 C7 H7A 110.0 . . ?
N4 C7 H7B 110.0 . . ?
C6 C7 H7B 110.0 . . ?
H7A C7 H7B 108.4 . . ?
N4 C8 C9 115.22(19) . . ?
N4 C8 H8A 108.5 . . ?
C9 C8 H8A 108.5 . . ?
N4 C8 H8B 108.5 . . ?
C9 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
C8 C9 C10 114.5(2) . . ?
C8 C9 H9A 108.6 . . ?
C10 C9 H9A 108.6 . . ?
C8 C9 H9B 108.6 . . ?
C10 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
N1 C10 C9 114.8(2) . . ?
N1 C10 H10A 108.6 . . ?
C9 C10 H10A 108.6 . . ?
N1 C10 H10B 108.6 . . ?
C9 C10 H10B 108.6 . . ?
H10A C10 H10B 107.5 . . ?
N1 C11 C12 111.37(19) . . ?
N1 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
N1 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
O1 C12 O2 125.2(2) . . ?
O1 C12 C11 123.1(2) . . ?
O2 C12 C11 111.6(2) . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 N2 112.09(18) . . ?
C15 C14 H14A 109.2 . . ?
N2 C14 H14A 109.2 . . ?
C15 C14 H14B 109.2 . . ?
N2 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C16 C15 C14 178.0(3) . . ?
C15 C16 H16 180.0 . . ?
C18 C17 N3 113.78(18) . . ?
C18 C17 H17A 108.8 . . ?
N3 C17 H17A 108.8 . . ?
C18 C17 H17B 108.8 . . ?
N3 C17 H17B 108.8 . . ?
H17A C17 H17B 107.7 . . ?
C19 C18 C17 176.8(2) . . ?
C18 C19 H19 180.0 . . ?
C21 C20 N4 113.30(18) . . ?
C21 C20 H20A 108.9 . . ?
N4 C20 H20A 108.9 . . ?
C21 C20 H20B 108.9 . . ?
N4 C20 H20B 108.9 . . ?
H20A C20 H20B 107.7 . . ?
C22 C21 C20 178.4(3) . . ?
C21 C22 H22 180.0 . . ?
O5 Cl1 O4 109.9(2) . . ?
O5 Cl1 O6 113.1(2) . . ?
O4 Cl1 O6 107.7(2) . . ?
O5 Cl1 O3 110.25(15) . . ?
O4 Cl1 O3 107.6(2) . . ?
O6 Cl1 O3 108.00(14) . . ?
Cl1 O3 Cu1 145.17(12) . . ?
O9A Cl2A O8A 114.1(12) . . ?
O9A Cl2A O7A 111.2(10) . . ?
O8A Cl2A O7A 106.8(9) . . ?
O9A Cl2A O10A 116.2(10) . . ?
O8A Cl2A O10A 105.5(9) . . ?
O7A Cl2A O10A 102.1(7) . . ?
O10B Cl2B O7B 111.3(7) . . ?
O10B Cl2B O8B 112.4(9) . . ?
O7B Cl2B O8B 112.7(10) . . ?
O10B Cl2B O9B 105.3(7) . . ?
O7B Cl2B O9B 105.7(8) . . ?
O8B Cl2B O9B 108.8(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
C11 N1 C1 C2 153.2(2) . . . . ?
C10 N1 C1 C2 -87.3(2) . . . . ?
Cu1 N1 C1 C2 34.2(2) . . . . ?
C3 N2 C2 C1 169.1(2) . . . . ?
C14 N2 C2 C1 -71.2(2) . . . . ?
Cu1 N2 C2 C1 51.6(2) . . . . ?
N1 C1 C2 N2 -60.4(3) . . . . ?
C2 N2 C3 C4 -172.3(2) . . . . ?
C14 N2 C3 C4 67.6(2) . . . . ?
Cu1 N2 C3 C4 -61.0(2) . . . . ?
N2 C3 C4 C5 70.0(3) . . . . ?
C17 N3 C5 C4 -67.9(3) . . . . ?
C6 N3 C5 C4 173.3(2) . . . . ?
Cu1 N3 C5 C4 57.3(2) . . . . ?
C3 C4 C5 N3 -67.5(3) . . . . ?
C5 N3 C6 C7 -87.5(2) . . . . ?
C17 N3 C6 C7 151.71(18) . . . . ?
Cu1 N3 C6 C7 32.97(19) . . . . ?
C20 N4 C7 C6 -70.2(2) . . . . ?
C8 N4 C7 C6 169.34(18) . . . . ?
Cu1 N4 C7 C6 48.64(19) . . . . ?
N3 C6 C7 N4 -56.5(2) . . . . ?
C7 N4 C8 C9 -174.95(19) . . . . ?
C20 N4 C8 C9 64.0(2) . . . . ?
Cu1 N4 C8 C9 -60.4(2) . . . . ?
N4 C8 C9 C10 67.9(3) . . . . ?
C11 N1 C10 C9 -70.3(3) . . . . ?
C1 N1 C10 C9 171.7(2) . . . . ?
Cu1 N1 C10 C9 56.6(3) . . . . ?
C8 C9 C10 N1 -65.6(3) . . . . ?
C10 N1 C11 C12 149.7(2) . . . . ?
C1 N1 C11 C12 -92.6(2) . . . . ?
Cu1 N1 C11 C12 21.5(2) . . . . ?
Cu1 O1 C12 O2 173.55(18) . . . . ?
Cu1 O1 C12 C11 -3.4(3) . . . . ?
C13 O2 C12 O1 -0.3(3) . . . . ?
C13 O2 C12 C11 176.9(2) . . . . ?
N1 C11 C12 O1 -12.1(3) . . . . ?
N1 C11 C12 O2 170.63(19) . . . . ?
C2 N2 C14 C15 -58.7(3) . . . . ?
C3 N2 C14 C15 60.0(3) . . . . ?
Cu1 N2 C14 C15 -173.52(17) . . . . ?
C5 N3 C17 C18 -61.8(3) . . . . ?
C6 N3 C17 C18 56.3(2) . . . . ?
Cu1 N3 C17 C18 171.91(15) . . . . ?
C7 N4 C20 C21 -53.9(2) . . . . ?
C8 N4 C20 C21 65.2(2) . . . . ?
Cu1 N4 C20 C21 -168.75(16) . . . . ?
O5 Cl1 O3 Cu1 -155.2(3) . . . . ?
O4 Cl1 O3 Cu1 84.9(3) . . . . ?
O6 Cl1 O3 Cu1 -31.1(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1A Cl2B^b 0.99 3.02 4.001(11) 171.5 2 yes
C1 H1A O9B^b 0.99 2.70 3.569(10) 146.4 2 yes
C1 H1A O10B^b 0.99 2.46 3.408(7) 160.2 2 yes
C3 H3B O3 0.99 2.43 3.356(3) 156.4 . yes
C3 H3B O6 0.99 2.59 3.383(4) 136.9 . yes
C4 H4A O9A^a 0.99 2.73 3.721(14) 175.7 . yes
C4 H4A O9B^b 0.99 2.52 3.508(11) 172.2 . yes
C4 H4B O6 0.99 2.50 3.419(3) 155.1 3_556 yes
C8 H8B O3 0.99 2.46 3.377(3) 154.3 . yes
C9 H9B O8A^a 0.99 2.53 3.270(16) 131.1 4_566 yes
C10 H10B O8A^a 0.99 2.50 3.419(14) 154.9 2 yes
C11 H11A O10A^a 0.99 2.34 3.180(6) 141.9 2_655 yes
C14 H14B Cl2A^a 0.99 2.92 3.749(9) 141.6 . yes
C14 H14B O7A^a 0.99 2.62 3.383(6) 133.6 . yes
C14 H14B O9A^a 0.99 2.63 3.548(16) 154.0 . yes
C14 H14B O9B^b 0.99 2.58 3.483(11) 152.0 . yes
C17 H17A O7A^a 0.99 2.51 3.246(5) 131.0 . yes
C17 H17A O9A^a 0.99 2.64 3.532(16) 149.3 . yes
C17 H17B O1 0.99 2.47 3.092(3) 120.2 . yes
C20 H20B O10A^a 0.99 2.32 3.222(7) 151.3 2_655 yes
C20 H20B O10B^b 0.99 2.22 2.925(5) 126.8 2_655 yes

_refine_diff_density_max         0.744
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.071

