# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_ydkr
_database_code_depnum_ccdc_archive 'CCDC 1521436'
#Added by publCIF



_audit_update_record             
;
2017-01-23 deposited with the CCDC.
2017-02-06 downloaded from the CCDC.
;
_publcif_datablock.id            {4e28e9f4-a5d0-414f-94ac-ba708aa1c453}
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         {(Hha)2[Cu(CA)2(EtOH)]}n
_chemical_formula_sum            'C26 H38 Cl4 Cu N2 O9'
_chemical_formula_weight         727.92

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cu Cu 0.3201 1.2651 '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'
O O 0.0106 0.0060 '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'
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'

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

_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                   9.9958(4)
_cell_length_b                   12.3264(5)
_cell_length_c                   14.0179(6)
_cell_angle_alpha                67.9707(16)
_cell_angle_beta                 89.4411(15)
_cell_angle_gamma                87.1956(13)
_cell_volume                     1599.09(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    13756
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      27.56

_exptl_crystal_description       block
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_F_000             754
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.069
_shelx_estimated_absorpt_T_min   0.674
_shelx_estimated_absorpt_T_max   0.856
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.774
_exptl_absorpt_correction_T_max  0.852
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            15881
_diffrn_reflns_av_unetI/netI     0.0254
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.136
_diffrn_reflns_theta_max         27.486
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             7289
_reflns_number_gt                6423
_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       'RAPID AUTO (Rigaku, 2011)'
_computing_cell_refinement       'RAPID AUTO (Rigaku, 2011)'
_computing_data_reduction        'RAPID AUTO (Rigaku, 2011)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_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)+(0.0460P)²+0.9296P] 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         7289
_refine_ls_number_parameters     419
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0357
_refine_ls_R_factor_gt           0.0310
_refine_ls_wR_factor_ref         0.0897
_refine_ls_wR_factor_gt          0.0843
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.097
_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 0.24071(2) 0.23189(2) 0.42243(2) 0.01409(7) Uani 1 1 d . . . . .
Cl1 Cl -0.00450(4) 0.37751(4) 0.66501(3) 0.01824(10) Uani 1 1 d . . . . .
Cl2 Cl -0.20372(4) 0.32093(4) 0.25721(3) 0.01784(10) Uani 1 1 d . . . . .
Cl3 Cl 0.48504(4) 0.07039(4) 0.19317(3) 0.01837(10) Uani 1 1 d . . . . .
Cl4 Cl 0.68171(4) 0.13833(4) 0.59564(3) 0.01422(9) Uani 1 1 d . . . . .
O1 O 0.06374(12) 0.25103(11) 0.36164(9) 0.0159(2) Uani 1 1 d . . . . .
O2 O 0.14910(12) 0.28423(11) 0.52345(9) 0.0166(3) Uani 1 1 d . . . . .
O3 O -0.27620(13) 0.44408(12) 0.56284(11) 0.0207(3) Uani 1 1 d . . . . .
O4 O -0.35448(13) 0.42943(12) 0.38934(10) 0.0216(3) Uani 1 1 d . . . . .
O5 O 0.40969(12) 0.19066(11) 0.49779(9) 0.0148(2) Uani 1 1 d . . . . .
O6 O 0.32625(12) 0.15952(11) 0.33455(9) 0.0150(2) Uani 1 1 d . . . . .
O7 O 0.75924(12) 0.01369(11) 0.29151(10) 0.0174(3) Uani 1 1 d . . . . .
O8 O 0.83494(12) 0.02539(11) 0.47122(9) 0.0172(3) Uani 1 1 d . . . . .
O9 O 0.29645(16) 0.41423(12) 0.32839(11) 0.0237(3) Uani 1 1 d . . . . .
N1 N 0.96835(16) -0.04740(14) 0.67898(12) 0.0159(3) Uani 1 1 d . . . . .
N2 N 0.45939(16) 0.35524(14) 0.59017(12) 0.0201(3) Uani 0.8 1 d . . P . .
H2A H 0.394343 0.413753 0.569260 0.030 Uiso 0.8 1 calc R U P . .
H2B H 0.438990 0.297692 0.567628 0.030 Uiso 0.8 1 calc R U P . .
H2C H 0.539399 0.384255 0.563672 0.030 Uiso 0.8 1 calc R U P . .
C1 C -0.02249(17) 0.30014(14) 0.40371(13) 0.0131(3) Uani 1 1 d . . . . .
C2 C 0.02752(17) 0.31654(14) 0.49927(13) 0.0134(3) Uani 1 1 d . . . . .
C3 C -0.05941(18) 0.36299(15) 0.55415(13) 0.0145(3) Uani 1 1 d . . . . .
C4 C -0.19110(17) 0.40086(15) 0.51936(13) 0.0150(3) Uani 1 1 d . . . . .
C5 C -0.23977(17) 0.39087(15) 0.41882(14) 0.0154(3) Uani 1 1 d . . . . .
C6 C -0.15014(17) 0.33748(15) 0.36752(13) 0.0141(3) Uani 1 1 d . . . . .
C7 C 0.49888(17) 0.14868(14) 0.45242(13) 0.0127(3) Uani 1 1 d . . . . .
C8 C 0.45036(17) 0.12989(14) 0.35785(13) 0.0128(3) Uani 1 1 d . . . . .
C9 C 0.53853(17) 0.08569(15) 0.30412(13) 0.0141(3) Uani 1 1 d . . . . .
C10 C 0.67487(17) 0.05179(15) 0.33687(13) 0.0134(3) Uani 1 1 d . . . . .
C11 C 0.72068(17) 0.06413(15) 0.43803(13) 0.0129(3) Uani 1 1 d . . . . .
C12 C 0.62901(17) 0.11803(15) 0.48644(13) 0.0129(3) Uani 1 1 d . . . . .
C13 C 0.2948(3) 0.4710(2) 0.21911(16) 0.0345(5) Uani 1 1 d . . . . .
H13A H 0.292922 0.557012 0.199925 0.041 Uiso 1 1 calc R U . . .
H13B H 0.213121 0.451627 0.190669 0.041 Uiso 1 1 calc R U . . .
C14 C 0.4174(3) 0.4323(2) 0.17416(19) 0.0418(6) Uani 1 1 d . . . . .
H14A H 0.416687 0.473820 0.099291 0.063 Uiso 1 1 calc R U . . .
H14B H 0.416875 0.347684 0.190521 0.063 Uiso 1 1 calc R U . . .
H14C H 0.498130 0.450078 0.203489 0.063 Uiso 1 1 calc R U . . .
C15 C 0.91050(18) -0.05845(16) 0.78005(13) 0.0164(3) Uani 1 1 d . . . . .
H15A H 0.959391 -0.122932 0.835450 0.020 Uiso 1 1 calc R U . . .
H15B H 0.815609 -0.078660 0.781892 0.020 Uiso 1 1 calc R U . . .
C16 C 0.91867(18) 0.05425(16) 0.79958(13) 0.0165(3) Uani 1 1 d . . . . .
H16A H 0.878897 0.120519 0.740383 0.020 Uiso 1 1 calc R U . . .
H16B H 1.013763 0.069629 0.806098 0.020 Uiso 1 1 calc R U . . .
C17 C 0.84477(19) 0.04601(17) 0.89733(14) 0.0202(4) Uani 1 1 d . . . . .
H17A H 0.751914 0.023976 0.892394 0.024 Uiso 1 1 calc R U . . .
H17B H 0.888871 -0.017329 0.956538 0.024 Uiso 1 1 calc R U . . .
C18 C 0.8400(2) 0.15850(17) 0.91809(14) 0.0215(4) Uani 1 1 d . . . . .
H18A H 0.797994 0.222576 0.858320 0.026 Uiso 1 1 calc R U . . .
H18B H 0.932635 0.179430 0.925493 0.026 Uiso 1 1 calc R U . . .
C19 C 0.7621(2) 0.14838(19) 1.01453(16) 0.0287(5) Uani 1 1 d . . . . .
H19A H 0.670393 0.125026 1.007730 0.034 Uiso 1 1 calc R U . . .
H19B H 0.805622 0.085446 1.074320 0.034 Uiso 1 1 calc R U . . .
C20 C 0.7526(3) 0.2605(2) 1.03568(17) 0.0352(5) Uani 1 1 d . . . . .
H20A H 0.699453 0.248282 1.097684 0.053 Uiso 1 1 calc R U . . .
H20B H 0.709360 0.323464 0.976978 0.053 Uiso 1 1 calc R U . . .
H20C H 0.842690 0.282329 1.046027 0.053 Uiso 1 1 calc R U . . .
C21 C 0.4684(3) 0.3055(2) 0.70607(19) 0.0245(5) Uani 0.8 1 d D . P . .
H21A H 0.474556 0.369806 0.731762 0.029 Uiso 0.8 1 calc R U P . .
H21B H 0.549584 0.252919 0.728954 0.029 Uiso 0.8 1 calc R U P . .
C22 C 0.3451(3) 0.2382(2) 0.7485(2) 0.0291(5) Uani 0.8 1 d D . P . .
H22A H 0.338895 0.174914 0.721659 0.035 Uiso 0.8 1 calc R U P . .
H22B H 0.264359 0.291380 0.725195 0.035 Uiso 0.8 1 calc R U P . .
C23 C 0.3493(4) 0.1845(3) 0.8673(2) 0.0469(8) Uani 0.8 1 d D . P . .
H23A H 0.277072 0.128523 0.890764 0.056 Uiso 0.8 1 calc R U P . .
H23B H 0.435484 0.138815 0.888885 0.056 Uiso 0.8 1 calc R U P . .
C24 C 0.3351(4) 0.2667(3) 0.9226(2) 0.0464(8) Uani 0.8 1 d D . P . .
H24A H 0.341269 0.220757 0.997611 0.056 Uiso 0.8 1 calc R U P . .
H24B H 0.410957 0.319287 0.903904 0.056 Uiso 0.8 1 calc R U P . .
C25 C 0.2077(4) 0.3394(4) 0.9001(3) 0.0558(10) Uani 0.8 1 d D . P . .
H25A H 0.133028 0.288727 0.902118 0.067 Uiso 0.8 1 calc R U P . .
H25B H 0.211429 0.399169 0.829403 0.067 Uiso 0.8 1 calc R U P . .
C26 C 0.1767(6) 0.4031(4) 0.9768(3) 0.0685(13) Uani 0.8 1 d D . P . .
H26A H 0.185683 0.346308 1.047692 0.103 Uiso 0.8 1 calc R U P . .
H26B H 0.085102 0.437865 0.964877 0.103 Uiso 0.8 1 calc R U P . .
H26C H 0.239979 0.464923 0.965526 0.103 Uiso 0.8 1 calc R U P . .
N2A N 0.45939(16) 0.35524(14) 0.59017(12) 0.0201(3) Uani 0.2 1 d . . P A 1
H2AA H 0.489508 0.419275 0.599147 0.030 Uiso 0.2 1 calc R U P A 1
H2AB H 0.395017 0.378238 0.540132 0.030 Uiso 0.2 1 calc R U P A 1
H2AC H 0.528667 0.317170 0.571247 0.030 Uiso 0.2 1 calc R U P A 1
C27 C 0.4002(11) 0.2725(9) 0.6915(8) 0.0245(5) Uani 0.2 1 d D . P A 1
H27A H 0.302576 0.289526 0.693271 0.029 Uiso 0.2 1 calc R U P A 1
H27B H 0.415439 0.189909 0.698427 0.029 Uiso 0.2 1 calc R U P A 1
C28 C 0.4708(11) 0.2936(9) 0.7779(8) 0.0291(5) Uani 0.2 1 d D . P A 1
H28A H 0.567864 0.274919 0.774984 0.035 Uiso 0.2 1 calc R U P A 1
H28B H 0.459288 0.377758 0.766520 0.035 Uiso 0.2 1 calc R U P A 1
C29 C 0.4216(15) 0.2234(12) 0.8827(9) 0.0469(8) Uani 0.2 1 d D . P A 1
H29A H 0.476880 0.238975 0.933915 0.056 Uiso 0.2 1 calc R U P A 1
H29B H 0.435832 0.139249 0.894490 0.056 Uiso 0.2 1 calc R U P A 1
C30 C 0.2734(15) 0.2470(12) 0.9024(11) 0.0464(8) Uani 0.2 1 d D . P A 1
H30A H 0.215971 0.243118 0.846728 0.056 Uiso 0.2 1 calc R U P A 1
H30B H 0.244586 0.188648 0.968823 0.056 Uiso 0.2 1 calc R U P A 1
C31 C 0.2648(17) 0.3681(14) 0.9046(14) 0.0558(10) Uani 0.2 1 d D . P A 1
H31A H 0.282638 0.426629 0.835319 0.067 Uiso 0.2 1 calc R U P A 1
H31B H 0.332766 0.374273 0.953030 0.067 Uiso 0.2 1 calc R U P A 1
C32 C 0.1234(19) 0.3922(16) 0.9393(14) 0.0685(13) Uani 0.2 1 d D . P A 1
H32A H 0.113933 0.473681 0.934299 0.103 Uiso 0.2 1 calc R U P A 1
H32B H 0.110121 0.339514 1.010769 0.103 Uiso 0.2 1 calc R U P A 1
H32C H 0.056343 0.378749 0.894956 0.103 Uiso 0.2 1 calc R U P A 1
H1 H 0.274(3) 0.455(3) 0.351(2) 0.042(9) Uiso 1 1 d . . . . .
H2 H 1.053(3) -0.023(2) 0.6726(19) 0.030(6) Uiso 1 1 d . . . . .
H3 H 0.966(2) -0.115(2) 0.6716(17) 0.021(6) Uiso 1 1 d . . . . .
H4 H 0.917(2) -0.001(2) 0.6310(18) 0.019(5) 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 O1 1.9362(12) . ?
Cu1 O6 1.9425(12) . ?
Cu1 O5 1.9431(12) . ?
Cu1 O2 1.9653(12) . ?
Cu1 O9 2.2328(14) . ?
Cl1 C3 1.7272(17) . ?
Cl2 C6 1.7272(17) . ?
Cl3 C9 1.7281(17) . ?
Cl4 C12 1.7319(17) . ?
O1 C1 1.290(2) . ?
O2 C2 1.269(2) . ?
O3 C4 1.252(2) . ?
O4 C5 1.233(2) . ?
O5 C7 1.288(2) . ?
O6 C8 1.286(2) . ?
O7 C10 1.229(2) . ?
O8 C11 1.241(2) . ?
O9 C13 1.425(2) . ?
O9 H1 0.71(3) . ?
N1 C15 1.486(2) . ?
N1 H2 0.91(3) . ?
N1 H3 0.88(2) . ?
N1 H4 0.86(2) . ?
N2 C21 1.508(3) . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N2 H2C 0.9100 . ?
C1 C6 1.370(2) . ?
C1 C2 1.520(2) . ?
C2 C3 1.394(2) . ?
C3 C4 1.404(2) . ?
C4 C5 1.545(2) . ?
C5 C6 1.427(2) . ?
C7 C12 1.375(2) . ?
C7 C8 1.517(2) . ?
C8 C9 1.374(2) . ?
C9 C10 1.434(2) . ?
C10 C11 1.557(2) . ?
C11 C12 1.417(2) . ?
C13 C14 1.510(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.519(2) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.522(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.519(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.520(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.517(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C22 1.509(4) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.544(4) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.490(5) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.487(5) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.572(5) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C28 1.518(12) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.490(13) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.538(15) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.503(15) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.541(17) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 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
O1 Cu1 O6 96.04(5) . . ?
O1 Cu1 O5 171.52(5) . . ?
O6 Cu1 O5 84.36(5) . . ?
O1 Cu1 O2 83.95(5) . . ?
O6 Cu1 O2 172.51(5) . . ?
O5 Cu1 O2 94.55(5) . . ?
O1 Cu1 O9 94.47(6) . . ?
O6 Cu1 O9 95.96(5) . . ?
O5 Cu1 O9 93.91(5) . . ?
O2 Cu1 O9 91.51(5) . . ?
C1 O1 Cu1 112.56(10) . . ?
C2 O2 Cu1 112.38(11) . . ?
C7 O5 Cu1 112.24(10) . . ?
C8 O6 Cu1 112.66(11) . . ?
C13 O9 Cu1 127.92(13) . . ?
C13 O9 H1 109(2) . . ?
Cu1 O9 H1 112(2) . . ?
C15 N1 H2 111.7(15) . . ?
C15 N1 H3 109.3(15) . . ?
H2 N1 H3 111(2) . . ?
C15 N1 H4 108.9(15) . . ?
H2 N1 H4 112(2) . . ?
H3 N1 H4 104(2) . . ?
C21 N2 H2A 109.5 . . ?
C21 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C21 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
O1 C1 C6 124.67(15) . . ?
O1 C1 C2 114.98(14) . . ?
C6 C1 C2 120.34(15) . . ?
O2 C2 C3 124.75(15) . . ?
O2 C2 C1 115.37(15) . . ?
C3 C2 C1 119.88(15) . . ?
C2 C3 C4 120.85(15) . . ?
C2 C3 Cl1 120.04(13) . . ?
C4 C3 Cl1 119.10(13) . . ?
O3 C4 C3 125.59(16) . . ?
O3 C4 C5 115.05(15) . . ?
C3 C4 C5 119.36(15) . . ?
O4 C5 C6 124.91(16) . . ?
O4 C5 C4 116.93(15) . . ?
C6 C5 C4 118.17(15) . . ?
C1 C6 C5 121.24(15) . . ?
C1 C6 Cl2 119.59(13) . . ?
C5 C6 Cl2 119.17(13) . . ?
O5 C7 C12 124.23(15) . . ?
O5 C7 C8 115.38(14) . . ?
C12 C7 C8 120.36(15) . . ?
O6 C8 C9 125.56(15) . . ?
O6 C8 C7 114.86(14) . . ?
C9 C8 C7 119.57(15) . . ?
C8 C9 C10 122.09(15) . . ?
C8 C9 Cl3 119.53(13) . . ?
C10 C9 Cl3 118.37(13) . . ?
O7 C10 C9 125.34(15) . . ?
O7 C10 C11 116.98(15) . . ?
C9 C10 C11 117.68(14) . . ?
O8 C11 C12 124.34(15) . . ?
O8 C11 C10 117.71(14) . . ?
C12 C11 C10 117.95(14) . . ?
C7 C12 C11 122.02(15) . . ?
C7 C12 Cl4 119.60(13) . . ?
C11 C12 Cl4 118.29(13) . . ?
O9 C13 C14 110.22(19) . . ?
O9 C13 H13A 109.6 . . ?
C14 C13 H13A 109.6 . . ?
O9 C13 H13B 109.6 . . ?
C14 C13 H13B 109.6 . . ?
H13A C13 H13B 108.1 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 C16 111.72(15) . . ?
N1 C15 H15A 109.3 . . ?
C16 C15 H15A 109.3 . . ?
N1 C15 H15B 109.3 . . ?
C16 C15 H15B 109.3 . . ?
H15A C15 H15B 107.9 . . ?
C15 C16 C17 110.92(15) . . ?
C15 C16 H16A 109.5 . . ?
C17 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C17 C16 H16B 109.5 . . ?
H16A C16 H16B 108.0 . . ?
C18 C17 C16 114.06(15) . . ?
C18 C17 H17A 108.7 . . ?
C16 C17 H17A 108.7 . . ?
C18 C17 H17B 108.7 . . ?
C16 C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?
C17 C18 C19 112.72(16) . . ?
C17 C18 H18A 109.0 . . ?
C19 C18 H18A 109.0 . . ?
C17 C18 H18B 109.0 . . ?
C19 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C20 C19 C18 113.88(18) . . ?
C20 C19 H19A 108.8 . . ?
C18 C19 H19A 108.8 . . ?
C20 C19 H19B 108.8 . . ?
C18 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N2 C21 C22 108.9(2) . . ?
N2 C21 H21A 109.9 . . ?
C22 C21 H21A 109.9 . . ?
N2 C21 H21B 109.9 . . ?
C22 C21 H21B 109.9 . . ?
H21A C21 H21B 108.3 . . ?
C21 C22 C23 111.1(2) . . ?
C21 C22 H22A 109.4 . . ?
C23 C22 H22A 109.4 . . ?
C21 C22 H22B 109.4 . . ?
C23 C22 H22B 109.4 . . ?
H22A C22 H22B 108.0 . . ?
C24 C23 C22 117.4(3) . . ?
C24 C23 H23A 107.9 . . ?
C22 C23 H23A 107.9 . . ?
C24 C23 H23B 107.9 . . ?
C22 C23 H23B 107.9 . . ?
H23A C23 H23B 107.2 . . ?
C25 C24 C23 114.1(3) . . ?
C25 C24 H24A 108.7 . . ?
C23 C24 H24A 108.7 . . ?
C25 C24 H24B 108.7 . . ?
C23 C24 H24B 108.7 . . ?
H24A C24 H24B 107.6 . . ?
C24 C25 C26 114.0(3) . . ?
C24 C25 H25A 108.7 . . ?
C26 C25 H25A 108.7 . . ?
C24 C25 H25B 108.7 . . ?
C26 C25 H25B 108.7 . . ?
H25A C25 H25B 107.6 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C28 C27 H27A 110.4 . . ?
C28 C27 H27B 110.4 . . ?
H27A C27 H27B 108.6 . . ?
C29 C28 C27 114.1(10) . . ?
C29 C28 H28A 108.7 . . ?
C27 C28 H28A 108.7 . . ?
C29 C28 H28B 108.7 . . ?
C27 C28 H28B 108.7 . . ?
H28A C28 H28B 107.6 . . ?
C28 C29 C30 115.5(11) . . ?
C28 C29 H29A 108.4 . . ?
C30 C29 H29A 108.4 . . ?
C28 C29 H29B 108.4 . . ?
C30 C29 H29B 108.4 . . ?
H29A C29 H29B 107.5 . . ?
C31 C30 C29 105.5(13) . . ?
C31 C30 H30A 110.6 . . ?
C29 C30 H30A 110.6 . . ?
C31 C30 H30B 110.6 . . ?
C29 C30 H30B 110.6 . . ?
H30A C30 H30B 108.8 . . ?
C30 C31 C32 108.9(13) . . ?
C30 C31 H31A 109.9 . . ?
C32 C31 H31A 109.9 . . ?
C30 C31 H31B 109.9 . . ?
C32 C31 H31B 109.9 . . ?
H31A C31 H31B 108.3 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 C1 C6 171.34(14) . . . . ?
Cu1 O1 C1 C2 -7.96(18) . . . . ?
Cu1 O2 C2 C3 -176.78(14) . . . . ?
Cu1 O2 C2 C1 4.03(18) . . . . ?
O1 C1 C2 O2 2.6(2) . . . . ?
C6 C1 C2 O2 -176.68(16) . . . . ?
O1 C1 C2 C3 -176.59(15) . . . . ?
C6 C1 C2 C3 4.1(3) . . . . ?
O2 C2 C3 C4 177.40(16) . . . . ?
C1 C2 C3 C4 -3.4(3) . . . . ?
O2 C2 C3 Cl1 -1.2(3) . . . . ?
C1 C2 C3 Cl1 177.97(12) . . . . ?
C2 C3 C4 O3 -179.69(17) . . . . ?
Cl1 C3 C4 O3 -1.1(3) . . . . ?
C2 C3 C4 C5 -0.1(3) . . . . ?
Cl1 C3 C4 C5 178.53(12) . . . . ?
O3 C4 C5 O4 2.4(2) . . . . ?
C3 C4 C5 O4 -177.28(16) . . . . ?
O3 C4 C5 C6 -177.19(16) . . . . ?
C3 C4 C5 C6 3.2(2) . . . . ?
O1 C1 C6 C5 179.83(16) . . . . ?
C2 C1 C6 C5 -0.9(3) . . . . ?
O1 C1 C6 Cl2 -0.7(3) . . . . ?
C2 C1 C6 Cl2 178.58(12) . . . . ?
O4 C5 C6 C1 177.92(17) . . . . ?
C4 C5 C6 C1 -2.6(3) . . . . ?
O4 C5 C6 Cl2 -1.6(3) . . . . ?
C4 C5 C6 Cl2 177.96(12) . . . . ?
Cu1 O5 C7 C12 176.58(14) . . . . ?
Cu1 O5 C7 C8 -5.54(18) . . . . ?
Cu1 O6 C8 C9 -174.50(14) . . . . ?
Cu1 O6 C8 C7 4.60(17) . . . . ?
O5 C7 C8 O6 0.7(2) . . . . ?
C12 C7 C8 O6 178.62(15) . . . . ?
O5 C7 C8 C9 179.81(15) . . . . ?
C12 C7 C8 C9 -2.2(2) . . . . ?
O6 C8 C9 C10 -178.31(16) . . . . ?
C7 C8 C9 C10 2.6(3) . . . . ?
O6 C8 C9 Cl3 1.9(3) . . . . ?
C7 C8 C9 Cl3 -177.15(12) . . . . ?
C8 C9 C10 O7 -178.66(17) . . . . ?
Cl3 C9 C10 O7 1.1(2) . . . . ?
C8 C9 C10 C11 1.3(2) . . . . ?
Cl3 C9 C10 C11 -178.96(12) . . . . ?
O7 C10 C11 O8 -6.2(2) . . . . ?
C9 C10 C11 O8 173.84(15) . . . . ?
O7 C10 C11 C12 174.19(16) . . . . ?
C9 C10 C11 C12 -5.7(2) . . . . ?
O5 C7 C12 C11 175.24(16) . . . . ?
C8 C7 C12 C11 -2.5(3) . . . . ?
O5 C7 C12 Cl4 -1.3(2) . . . . ?
C8 C7 C12 Cl4 -179.10(12) . . . . ?
O8 C11 C12 C7 -173.19(16) . . . . ?
C10 C11 C12 C7 6.4(2) . . . . ?
O8 C11 C12 Cl4 3.4(2) . . . . ?
C10 C11 C12 Cl4 -177.04(11) . . . . ?
Cu1 O9 C13 C14 -79.2(2) . . . . ?
N1 C15 C16 C17 173.44(14) . . . . ?
C15 C16 C17 C18 -175.89(15) . . . . ?
C16 C17 C18 C19 178.33(17) . . . . ?
C17 C18 C19 C20 -178.49(19) . . . . ?
N2 C21 C22 C23 179.6(2) . . . . ?
C21 C22 C23 C24 69.3(4) . . . . ?
C22 C23 C24 C25 59.4(5) . . . . ?
C23 C24 C25 C26 166.1(4) . . . . ?
C27 C28 C29 C30 -61.7(15) . . . . ?
C28 C29 C30 C31 -69.5(16) . . . . ?
C29 C30 C31 C32 -172.0(13) . . . . ?

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
N2 H2A O3 0.91 2.30 3.119(2) 149.1 2_566
N2 H2A O4 0.91 2.23 2.919(2) 131.6 2_566
N2 H2B O5 0.91 1.95 2.850(2) 170.3 .
N2 H2C O3 0.91 2.02 2.878(2) 157.2 1_655
N2 H2C O4 0.91 2.53 3.218(2) 132.9 1_655
C16 H16A Cl4 0.99 2.78 3.5393(18) 133.5 .
N2A H2C O3 0.91 2.02 2.878(2) 157.2 1_655
N2A H2A O4 0.91 2.23 2.919(2) 131.6 2_566
N2A H2A O3 0.91 2.30 3.119(2) 149.1 2_566
N2A H2AC Cl4 0.91 2.54 3.3706(16) 152.7 .
O9 H1 O3 0.71(3) 2.04(3) 2.7154(19) 159(3) 2_566
N1 H2 O7 0.91(3) 1.97(3) 2.832(2) 160(2) 2_756
N1 H2 O8 0.91(3) 2.30(3) 2.814(2) 115.4(19) 2_756
N1 H3 O1 0.88(2) 1.93(2) 2.807(2) 170(2) 2_656
N1 H4 Cl4 0.86(2) 2.78(2) 3.4975(16) 142.7(19) .
N1 H4 O8 0.86(2) 2.29(2) 3.011(2) 142(2) .

_refine_diff_density_max         1.156
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.091


loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?
####################################################################### 
# 
# 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_ydkr
_database_code_depnum_ccdc_archive 'CCDC 1521424'
#Added by publCIF



_audit_update_record             
;
2017-01-23 deposited with the CCDC.
2017-02-06 downloaded from the CCDC.
;


_diffrn_radiation_monochromator  ?
#Added by publCIF




_diffrn_radiation_source         ?
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         {(Hha)2[Cu(CA)2(EtOH)2]}n
_chemical_formula_sum            'C28 H44 Cl4 Cu N2 O10'
_chemical_formula_weight         773.99

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           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

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

_cell_length_a                   9.8642(19)
_cell_length_b                   16.051(3)
_cell_length_c                   11.379(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.283(5)
_cell_angle_gamma                90
_cell_volume                     1801.3(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8077
_cell_measurement_theta_min      3.04
_cell_measurement_theta_max      27.92

_exptl_crystal_description       platelet
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_F_000             806
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.956
_shelx_estimated_absorpt_T_min   0.832
_shelx_estimated_absorpt_T_max   0.832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_T_max  0.953
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Rigaku Saturn70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.143
_diffrn_reflns_number            14394
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_av_R_equivalents  0.0738
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.582
_diffrn_reflns_theta_max         27.482
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2137
_reflns_number_gt                1200
_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       PROCESS-AUTO
_computing_cell_refinement       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_structure_solution    'Superflip (Palatinus, et al., 2007)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_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)+(0.1214P)²+1.7609P] 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         2137
_refine_ls_number_parameters     153
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.1271
_refine_ls_R_factor_gt           0.0750
_refine_ls_wR_factor_ref         0.2428
_refine_ls_wR_factor_gt          0.2032
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_restrained_S_all      1.095
_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 1.000000 0.500000 0.500000 0.0871(6) Uani 1 4 d S T P . .
Cl1 Cl 0.76223(12) 0.73692(11) 0.30773(11) 0.0935(6) Uani 1 1 d . . . . .
O1 O 0.8984(3) 0.5901(3) 0.4241(3) 0.0888(12) Uani 1 1 d . . . . .
O2 O 0.9014(4) 0.8831(3) 0.4194(3) 0.1001(13) Uani 1 1 d . . . . .
O3 O 0.8420(7) 0.4734(6) 0.6539(6) 0.100(4) Uani 0.5 1 d D . P A -1
H19 H 0.769268 0.457861 0.625286 0.150 Uiso 0.5 1 calc R U P A -1
N1 N 0.6320(6) 0.5184(3) 0.3761(5) 0.049(2) Uani 0.5 1 d . . P B -1
H1A H 0.702151 0.553218 0.381451 0.074 Uiso 0.5 1 calc R U P B -1
H1B H 0.636043 0.482467 0.435577 0.074 Uiso 0.5 1 calc R U P B -1
H1C H 0.555095 0.547284 0.378944 0.074 Uiso 0.5 1 calc R U P B -1
C1 C 0.9417(4) 0.6630(5) 0.4544(4) 0.0802(16) Uani 1 1 d . . . . .
C2 C 0.8921(4) 0.7366(4) 0.4117(4) 0.0822(17) Uani 1 1 d . . . . .
C3 C 0.9426(4) 0.8138(5) 0.4527(4) 0.0842(17) Uani 1 1 d . . . . .
C4 C 0.8346(19) 0.4747(10) 0.7691(11) 0.132(8) Uani 0.5 1 d D . P A -1
H1 H 0.859505 0.419680 0.797465 0.159 Uiso 0.5 1 calc R U P A -1
H2 H 0.740106 0.483082 0.787903 0.159 Uiso 0.5 1 calc R U P A -1
C5 C 0.914(3) 0.5351(17) 0.8374(17) 0.22(2) Uani 0.5 1 d D . P A -1
H3 H 0.981165 0.559719 0.788355 0.332 Uiso 0.5 1 calc R U P A -1
H4 H 0.958190 0.507450 0.902568 0.332 Uiso 0.5 1 calc R U P A -1
H5 H 0.855290 0.577770 0.866103 0.332 Uiso 0.5 1 calc R U P A -1
C6 C 0.6368(12) 0.4701(7) 0.2577(9) 0.092(4) Uani 0.5 1 d D . P B -1
H6 H 0.707698 0.428258 0.261860 0.111 Uiso 0.5 1 calc R U P B -1
H7 H 0.550989 0.442088 0.242832 0.111 Uiso 0.5 1 calc R U P B -1
C7 C 0.6640(10) 0.5297(7) 0.1602(10) 0.093(5) Uani 0.5 1 d D . P B -1
H8 H 0.743132 0.562532 0.182237 0.111 Uiso 0.5 1 calc R U P B -1
H9 H 0.686662 0.497744 0.090985 0.111 Uiso 0.5 1 calc R U P B -1
C8 C 0.5514(12) 0.5879(9) 0.1278(10) 0.110(5) Uani 0.5 1 d D . P B -1
H10 H 0.528314 0.619414 0.197224 0.132 Uiso 0.5 1 calc R U P B -1
H11 H 0.472600 0.554972 0.105199 0.132 Uiso 0.5 1 calc R U P B -1
C9 C 0.5784(16) 0.6483(12) 0.0307(13) 0.138(7) Uani 0.5 1 d D . P B -1
H12 H 0.590520 0.618161 -0.042198 0.166 Uiso 0.5 1 calc R U P B -1
H13 H 0.661289 0.678754 0.048501 0.166 Uiso 0.5 1 calc R U P B -1
C10 C 0.462(3) 0.7089(14) 0.0159(19) 0.156(9) Uani 0.5 1 d D . P B -1
H14 H 0.382506 0.678660 -0.012209 0.187 Uiso 0.5 1 calc R U P B -1
H15 H 0.441265 0.731988 0.092269 0.187 Uiso 0.5 1 calc R U P B -1
C11 C 0.488(2) 0.7769(11) -0.0643(15) 0.156(7) Uani 0.5 1 d D . P B -1
H16 H 0.579245 0.795912 -0.053007 0.234 Uiso 0.5 1 calc R U P B -1
H17 H 0.426152 0.821782 -0.049297 0.234 Uiso 0.5 1 calc R U P B -1
H18 H 0.474539 0.757890 -0.143745 0.234 Uiso 0.5 1 calc R U P B -1


_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 O1 1.950(4) 2_756 ?
Cu1 O1 1.950(4) 5_766 ?
Cu1 O1 1.950(4) 6_565 ?
Cu1 O1 1.950(4) . ?
Cl1 C2 1.724(4) . ?
O1 C1 1.290(7) . ?
O2 C3 1.240(7) . ?
O3 C4 1.314(12) . ?
O3 H19 0.8200 . ?
N1 C6 1.557(12) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
C1 C2 1.363(8) . ?
C1 C1 1.532(7) 2_756 ?
C2 C3 1.411(9) . ?
C3 C3 1.545(8) 2_756 ?
C4 C5 1.460(16) . ?
C4 H1 0.9700 . ?
C4 H2 0.9700 . ?
C5 H3 0.9600 . ?
C5 H4 0.9600 . ?
C5 H5 0.9600 . ?
C6 C7 1.493(12) . ?
C6 H6 0.9700 . ?
C6 H7 0.9700 . ?
C7 C8 1.492(12) . ?
C7 H8 0.9700 . ?
C7 H9 0.9700 . ?
C8 C9 1.498(14) . ?
C8 H10 0.9700 . ?
C8 H11 0.9700 . ?
C9 C10 1.512(16) . ?
C9 H12 0.9700 . ?
C9 H13 0.9700 . ?
C10 C11 1.448(15) . ?
C10 H14 0.9700 . ?
C10 H15 0.9700 . ?
C11 H16 0.9600 . ?
C11 H17 0.9600 . ?
C11 H18 0.9600 . ?

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
O1 Cu1 O1 95.7(2) 2_756 5_766 ?
O1 Cu1 O1 180.00(15) 2_756 6_565 ?
O1 Cu1 O1 84.3(2) 5_766 6_565 ?
O1 Cu1 O1 84.3(2) 2_756 . ?
O1 Cu1 O1 180.0 5_766 . ?
O1 Cu1 O1 95.7(2) 6_565 . ?
C1 O1 Cu1 113.0(3) . . ?
C4 O3 H19 109.5 . . ?
C6 N1 H1A 109.5 . . ?
C6 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C6 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
O1 C1 C2 125.2(4) . . ?
O1 C1 C1 114.8(2) . 2_756 ?
C2 C1 C1 120.0(3) . 2_756 ?
C1 C2 C3 121.4(5) . . ?
C1 C2 Cl1 120.2(5) . . ?
C3 C2 Cl1 118.4(4) . . ?
O2 C3 C2 125.1(4) . . ?
O2 C3 C3 116.3(3) . 2_756 ?
C2 C3 C3 118.6(3) . 2_756 ?
O3 C4 C5 120.0(14) . . ?
O3 C4 H1 107.3 . . ?
C5 C4 H1 107.3 . . ?
O3 C4 H2 107.3 . . ?
C5 C4 H2 107.3 . . ?
H1 C4 H2 106.9 . . ?
C4 C5 H3 109.5 . . ?
C4 C5 H4 109.5 . . ?
H3 C5 H4 109.5 . . ?
C4 C5 H5 109.5 . . ?
H3 C5 H5 109.5 . . ?
H4 C5 H5 109.5 . . ?
C7 C6 N1 109.5(8) . . ?
C7 C6 H6 109.8 . . ?
N1 C6 H6 109.8 . . ?
C7 C6 H7 109.8 . . ?
N1 C6 H7 109.8 . . ?
H6 C6 H7 108.2 . . ?
C8 C7 C6 116.1(9) . . ?
C8 C7 H8 108.3 . . ?
C6 C7 H8 108.3 . . ?
C8 C7 H9 108.3 . . ?
C6 C7 H9 108.3 . . ?
H8 C7 H9 107.4 . . ?
C7 C8 C9 116.4(11) . . ?
C7 C8 H10 108.2 . . ?
C9 C8 H10 108.2 . . ?
C7 C8 H11 108.2 . . ?
C9 C8 H11 108.2 . . ?
H10 C8 H11 107.3 . . ?
C8 C9 C10 110.6(12) . . ?
C8 C9 H12 109.5 . . ?
C10 C9 H12 109.5 . . ?
C8 C9 H13 109.5 . . ?
C10 C9 H13 109.5 . . ?
H12 C9 H13 108.1 . . ?
C11 C10 C9 114.3(14) . . ?
C11 C10 H14 108.7 . . ?
C9 C10 H14 108.7 . . ?
C11 C10 H15 108.7 . . ?
C9 C10 H15 108.7 . . ?
H14 C10 H15 107.6 . . ?
C10 C11 H16 109.5 . . ?
C10 C11 H17 109.5 . . ?
H16 C11 H17 109.5 . . ?
C10 C11 H18 109.5 . . ?
H16 C11 H18 109.5 . . ?
H17 C11 H18 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 C1 C2 177.7(4) . . . . ?
Cu1 O1 C1 C1 -2.2(6) . . . 2_756 ?
O1 C1 C2 C3 177.9(4) . . . . ?
C1 C1 C2 C3 -2.2(8) 2_756 . . . ?
O1 C1 C2 Cl1 -0.7(7) . . . . ?
C1 C1 C2 Cl1 179.2(4) 2_756 . . . ?
C1 C2 C3 O2 -178.9(5) . . . . ?
Cl1 C2 C3 O2 -0.3(7) . . . . ?
C1 C2 C3 C3 0.4(8) . . . 2_756 ?
Cl1 C2 C3 C3 179.0(4) . . . 2_756 ?
N1 C6 C7 C8 -70.6(12) . . . . ?
C6 C7 C8 C9 179.5(12) . . . . ?
C7 C8 C9 C10 -174.1(16) . . . . ?
C8 C9 C10 C11 171.6(19) . . . . ?

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
N1 H1A O1 0.89 2.07 2.909(7) 156.4 .
N1 H1B O2 0.89 2.33 3.206(8) 167.8 4_646
N1 H1C O2 0.89 1.95 2.822(7) 167.5 8_465
C6 H6 Cl1 0.97 2.75 3.587(11) 144.5 6_565
C6 H6 O1 0.97 2.62 3.311(11) 128.1 6_565

_refine_diff_density_max         0.400
_refine_diff_density_min         -0.968
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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_ydkr
_database_code_depnum_ccdc_archive 'CCDC 1521426'
#Added by publCIF



_audit_update_record             
;
2017-01-23 deposited with the CCDC.
2017-02-06 downloaded from the CCDC.
;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         {(Hha)2[Cu(CA)2(EtOH)]}n
_chemical_formula_sum            'C26 H38 Cl4 Cu N2 O9'
_chemical_formula_weight         727.92

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
Cl Cl 0.1484 0.1585 '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'
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'

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

_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                   9.9963(3)
_cell_length_b                   12.4259(4)
_cell_length_c                   14.1763(5)
_cell_angle_alpha                68.7310(14)
_cell_angle_beta                 88.9340(12)
_cell_angle_gamma                86.7180(10)
_cell_volume                     1638.25(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    12647
_cell_measurement_theta_min      3.09
_cell_measurement_theta_max      27.53

_exptl_crystal_description       block
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_F_000             754
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.043
_shelx_estimated_absorpt_T_min   0.680
_shelx_estimated_absorpt_T_max   0.859
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.779
_exptl_absorpt_correction_T_max  0.855
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_diffrn_ambient_temperature      250(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            16265
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.084
_diffrn_reflns_theta_max         27.483
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             7470
_reflns_number_gt                6073
_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       'RAPID AUTO (Rigaku, 2011)'
_computing_cell_refinement       'RAPID AUTO (Rigaku, 2011)'
_computing_data_reduction        'RAPID AUTO (Rigaku, 2011)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_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)+(0.0800P)²+0.2924P] 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         7470
_refine_ls_number_parameters     425
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0390
_refine_ls_wR_factor_ref         0.1280
_refine_ls_wR_factor_gt          0.1185
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.091
_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 0.24023(2) 0.23098(2) 0.42191(2) 0.03131(10) Uani 1 1 d . . . . .
Cl1 Cl -0.00584(6) 0.37887(5) 0.66157(4) 0.03941(15) Uani 1 1 d . . . . .
Cl2 Cl -0.20338(6) 0.31849(5) 0.26082(4) 0.03895(14) Uani 1 1 d . . . . .
Cl3 Cl 0.48788(6) 0.06757(6) 0.19563(4) 0.04062(15) Uani 1 1 d . . . . .
Cl4 Cl 0.67903(5) 0.13869(4) 0.59250(4) 0.03090(13) Uani 1 1 d . . . . .
O1 O 0.06326(14) 0.24879(14) 0.36344(12) 0.0325(3) Uani 1 1 d . . . . .
O2 O 0.14798(15) 0.28417(15) 0.52189(12) 0.0358(4) Uani 1 1 d . . . . .
O3 O -0.27749(15) 0.44234(15) 0.56401(14) 0.0429(4) Uani 1 1 d . . . . .
O4 O -0.35541(16) 0.42570(16) 0.39310(14) 0.0468(4) Uani 1 1 d . . . . .
O5 O 0.40872(14) 0.19169(13) 0.49517(11) 0.0313(3) Uani 1 1 d . . . . .
O6 O 0.32754(14) 0.15862(13) 0.33469(11) 0.0313(3) Uani 1 1 d . . . . .
O7 O 0.76039(15) 0.01093(15) 0.29284(13) 0.0383(4) Uani 1 1 d . . . . .
O8 O 0.83326(15) 0.02338(15) 0.47042(12) 0.0367(4) Uani 1 1 d . . . . .
O9 O 0.2918(2) 0.41320(17) 0.32828(15) 0.0527(5) Uani 1 1 d . . . . .
N1 N 0.9658(2) -0.0440(2) 0.67631(15) 0.0342(4) Uani 1 1 d . . . . .
C1 C -0.02330(19) 0.29868(17) 0.40456(16) 0.0269(4) Uani 1 1 d . . . . .
C2 C 0.0258(2) 0.31608(17) 0.49867(16) 0.0280(4) Uani 1 1 d . . . . .
C3 C -0.0606(2) 0.36279(18) 0.55253(16) 0.0288(4) Uani 1 1 d . . . . .
C4 C -0.1929(2) 0.39941(18) 0.52004(17) 0.0309(4) Uani 1 1 d . . . . .
C5 C -0.2406(2) 0.38813(18) 0.42097(17) 0.0312(4) Uani 1 1 d . . . . .
C6 C -0.1502(2) 0.33527(18) 0.36955(16) 0.0292(4) Uani 1 1 d . . . . .
C7 C 0.49836(19) 0.14806(17) 0.45108(15) 0.0254(4) Uani 1 1 d . . . . .
C8 C 0.45162(19) 0.12870(17) 0.35810(15) 0.0259(4) Uani 1 1 d . . . . .
C9 C 0.5405(2) 0.08395(19) 0.30509(15) 0.0287(4) Uani 1 1 d . . . . .
C10 C 0.6753(2) 0.04937(18) 0.33757(16) 0.0292(4) Uani 1 1 d . . . . .
C11 C 0.72013(19) 0.06228(18) 0.43749(16) 0.0275(4) Uani 1 1 d . . . . .
C12 C 0.62807(19) 0.11746(18) 0.48473(15) 0.0264(4) Uani 1 1 d . . . . .
C13 C 0.2925(4) 0.4668(3) 0.2219(3) 0.0774(10) Uani 1 1 d . . . . .
H13A H 0.289396 0.550888 0.203689 0.093 Uiso 1 1 calc R U . . .
H13B H 0.211908 0.447477 0.194418 0.093 Uiso 1 1 calc R U . . .
C14 C 0.4110(5) 0.4313(4) 0.1758(3) 0.1030(15) Uani 1 1 d . . . . .
H14A H 0.408843 0.473033 0.103203 0.154 Uiso 1 1 calc R U . . .
H14B H 0.411393 0.348868 0.189715 0.154 Uiso 1 1 calc R U . . .
H14C H 0.491208 0.448471 0.203936 0.154 Uiso 1 1 calc R U . . .
C15 C 0.9090(2) -0.0538(2) 0.77611(17) 0.0364(5) Uani 1 1 d . . . . .
H15A H 0.958904 -0.115900 0.829306 0.044 Uiso 1 1 calc R U . . .
H15B H 0.815616 -0.074772 0.779082 0.044 Uiso 1 1 calc R U . . .
C16 C 0.9146(2) 0.0571(2) 0.79606(18) 0.0393(5) Uani 1 1 d . . . . .
H16A H 0.873251 0.121031 0.739289 0.047 Uiso 1 1 calc R U . . .
H16B H 1.008398 0.073672 0.800877 0.047 Uiso 1 1 calc R U . . .
C17 C 0.8425(3) 0.0493(3) 0.8932(2) 0.0511(6) Uani 1 1 d . . . . .
H17A H 0.750627 0.027439 0.889423 0.061 Uiso 1 1 calc R U . . .
H17B H 0.887219 -0.012494 0.949780 0.061 Uiso 1 1 calc R U . . .
C18 C 0.8369(3) 0.1593(3) 0.9156(2) 0.0533(7) Uani 1 1 d . . . . .
H18A H 0.928592 0.180467 0.921055 0.064 Uiso 1 1 calc R U . . .
H18B H 0.793475 0.221645 0.858674 0.064 Uiso 1 1 calc R U . . .
C19 C 0.7623(4) 0.1498(3) 1.0115(2) 0.0673(9) Uani 1 1 d . . . . .
H19A H 0.671707 0.125931 1.006624 0.081 Uiso 1 1 calc R U . . .
H19B H 0.807433 0.088663 1.068371 0.081 Uiso 1 1 calc R U . . .
C20 C 0.7515(5) 0.2584(3) 1.0343(3) 0.0822(11) Uani 1 1 d . . . . .
H20A H 0.711206 0.242581 1.100425 0.123 Uiso 1 1 calc R U . . .
H20B H 0.696142 0.316539 0.983340 0.123 Uiso 1 1 calc R U . . .
H20C H 0.840150 0.286436 1.033951 0.123 Uiso 1 1 calc R U . . .
N2 N 0.4532(2) 0.35508(18) 0.58864(17) 0.0441(5) Uani 0.5 1 d . . P . .
H2A H 0.436649 0.298029 0.566192 0.066 Uiso 0.5 1 calc R U P . .
H2B H 0.530498 0.386504 0.561910 0.066 Uiso 0.5 1 calc R U P . .
H2C H 0.385735 0.409771 0.569852 0.066 Uiso 0.5 1 calc R U P . .
C21 C 0.4641(6) 0.3070(5) 0.7011(5) 0.0497(10) Uani 0.5 1 d D . P . .
H21A H 0.477859 0.369638 0.725812 0.060 Uiso 0.5 1 calc R U P . .
H21B H 0.541636 0.251654 0.721412 0.060 Uiso 0.5 1 calc R U P . .
C22 C 0.3391(8) 0.2475(8) 0.7474(6) 0.0810(15) Uani 0.5 1 d D . P . .
H22A H 0.331265 0.183092 0.723859 0.097 Uiso 0.5 1 calc R U P . .
H22B H 0.262901 0.302385 0.718732 0.097 Uiso 0.5 1 calc R U P . .
C23 C 0.3212(13) 0.1999(15) 0.8613(10) 0.108(4) Uani 0.5 1 d D . P . .
H23A H 0.238129 0.158847 0.878978 0.129 Uiso 0.5 1 calc R U P . .
H23B H 0.396301 0.145461 0.893426 0.129 Uiso 0.5 1 calc R U P . .
C24 C 0.316(3) 0.2966(16) 0.8968(17) 0.195(6) Uani 0.5 1 d D . P . .
H24A H 0.406021 0.301871 0.919989 0.234 Uiso 0.5 1 calc R U P . .
H24B H 0.296446 0.367109 0.837777 0.234 Uiso 0.5 1 calc R U P . .
C25 C 0.225(2) 0.2998(13) 0.9744(12) 0.178(5) Uani 0.5 1 d D . P . .
H25A H 0.277465 0.303012 1.031102 0.214 Uiso 0.5 1 calc R U P . .
H25B H 0.179047 0.227350 0.998820 0.214 Uiso 0.5 1 calc R U P . .
C26 C 0.1258(18) 0.3947(18) 0.9459(19) 0.220(14) Uani 0.5 1 d D . P . .
H26A H 0.037100 0.364673 0.956519 0.330 Uiso 0.5 1 calc R U P . .
H26B H 0.136703 0.441928 0.875049 0.330 Uiso 0.5 1 calc R U P . .
H26C H 0.136772 0.441312 0.986979 0.330 Uiso 0.5 1 calc R U P . .
N2A N 0.4532(2) 0.35508(18) 0.58864(17) 0.0441(5) Uani 0.5 1 d . . P A 1
H2AA H 0.542782 0.354015 0.594397 0.066 Uiso 0.5 1 calc R U P A 1
H2AB H 0.418310 0.427625 0.574577 0.066 Uiso 0.5 1 calc R U P A 1
H2AC H 0.432761 0.330724 0.538365 0.066 Uiso 0.5 1 calc R U P A 1
C27 C 0.3933(6) 0.2730(5) 0.6907(4) 0.0497(10) Uani 0.5 1 d D . P A 1
H27A H 0.296347 0.289138 0.692393 0.060 Uiso 0.5 1 calc R U P A 1
H27B H 0.409668 0.192026 0.697318 0.060 Uiso 0.5 1 calc R U P A 1
C28 C 0.4561(9) 0.2931(8) 0.7698(6) 0.0810(15) Uani 0.5 1 d D . P A 1
H28A H 0.442939 0.374667 0.762069 0.097 Uiso 0.5 1 calc R U P A 1
H28B H 0.552494 0.273339 0.770527 0.097 Uiso 0.5 1 calc R U P A 1
C29 C 0.3894(12) 0.2144(16) 0.8690(11) 0.108(4) Uani 0.5 1 d D . P A 1
H29A H 0.350817 0.152067 0.853309 0.129 Uiso 0.5 1 calc R U P A 1
H29B H 0.462474 0.178200 0.917220 0.129 Uiso 0.5 1 calc R U P A 1
C30 C 0.292(3) 0.2537(14) 0.9211(16) 0.195(6) Uani 0.5 1 d D . P A 1
H30A H 0.329551 0.233458 0.989124 0.234 Uiso 0.5 1 calc R U P A 1
H30B H 0.218314 0.202355 0.928920 0.234 Uiso 0.5 1 calc R U P A 1
C31 C 0.229(3) 0.3625(13) 0.9002(12) 0.178(5) Uani 0.5 1 d D . P A 1
H31A H 0.155308 0.370727 0.852842 0.214 Uiso 0.5 1 calc R U P A 1
H31B H 0.293225 0.420080 0.864597 0.214 Uiso 0.5 1 calc R U P A 1
C32 C 0.170(2) 0.3948(15) 0.9896(12) 0.171(9) Uani 0.5 1 d D . P A 1
H32A H 0.079887 0.428498 0.973072 0.256 Uiso 0.5 1 calc R U P A 1
H32B H 0.225903 0.450265 1.001288 0.256 Uiso 0.5 1 calc R U P A 1
H32C H 0.168757 0.325757 1.050251 0.256 Uiso 0.5 1 calc R U P A 1
H1 H 0.277(3) 0.458(3) 0.354(2) 0.054(9) Uiso 1 1 d . . . . .
H2 H 1.045(3) -0.027(2) 0.675(2) 0.042(8) Uiso 1 1 d . . . . .
H3 H 0.965(3) -0.107(3) 0.665(2) 0.059(9) Uiso 1 1 d . . . . .
H4 H 0.910(3) 0.002(3) 0.629(2) 0.058(9) 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 O1 1.9345(14) . ?
Cu1 O5 1.9382(14) . ?
Cu1 O6 1.9431(14) . ?
Cu1 O2 1.9640(15) . ?
Cu1 O9 2.254(2) . ?
Cl1 C3 1.731(2) . ?
Cl2 C6 1.726(2) . ?
Cl3 C9 1.731(2) . ?
Cl4 C12 1.732(2) . ?
O1 C1 1.286(2) . ?
O2 C2 1.274(2) . ?
O3 C4 1.248(3) . ?
O4 C5 1.230(3) . ?
O5 C7 1.287(2) . ?
O6 C8 1.288(2) . ?
O7 C10 1.228(2) . ?
O8 C11 1.234(3) . ?
O9 C13 1.410(4) . ?
O9 H1 0.78(3) . ?
N1 C15 1.480(3) . ?
N1 H2 0.83(3) . ?
N1 H3 0.86(3) . ?
N1 H4 0.89(3) . ?
C1 C6 1.362(3) . ?
C1 C2 1.521(3) . ?
C2 C3 1.380(3) . ?
C3 C4 1.403(3) . ?
C4 C5 1.547(3) . ?
C5 C6 1.426(3) . ?
C7 C12 1.374(3) . ?
C7 C8 1.510(3) . ?
C8 C9 1.373(3) . ?
C9 C10 1.424(3) . ?
C10 C11 1.559(3) . ?
C11 C12 1.415(3) . ?
C13 C14 1.465(6) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 H14C 0.9700 . ?
C15 C16 1.508(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C16 C17 1.517(3) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C17 C18 1.509(4) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C18 C19 1.508(4) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C19 C20 1.495(4) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 H20C 0.9700 . ?
N2 C21 1.489(6) . ?
N2 H2A 0.9000 . ?
N2 H2B 0.9000 . ?
N2 H2C 0.9000 . ?
C21 C22 1.504(9) . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C22 C23 1.516(13) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C23 C24 1.459(17) . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C24 C25 1.421(15) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C25 C26 1.441(16) . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 H26C 0.9700 . ?
C27 C28 1.401(8) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C28 C29 1.556(13) . ?
C28 H28A 0.9800 . ?
C28 H28B 0.9800 . ?
C29 C30 1.384(15) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C30 C31 1.390(16) . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C31 C32 1.557(16) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C32 H32C 0.9700 . ?

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
O1 Cu1 O5 171.44(7) . . ?
O1 Cu1 O6 96.38(6) . . ?
O5 Cu1 O6 84.33(6) . . ?
O1 Cu1 O2 83.85(6) . . ?
O5 Cu1 O2 94.37(6) . . ?
O6 Cu1 O2 172.74(7) . . ?
O1 Cu1 O9 93.75(8) . . ?
O5 Cu1 O9 94.66(7) . . ?
O6 Cu1 O9 96.21(7) . . ?
O2 Cu1 O9 91.01(7) . . ?
C1 O1 Cu1 112.83(12) . . ?
C2 O2 Cu1 112.40(13) . . ?
C7 O5 Cu1 112.42(12) . . ?
C8 O6 Cu1 112.54(12) . . ?
C13 O9 Cu1 128.0(2) . . ?
C13 O9 H1 111(2) . . ?
Cu1 O9 H1 115(2) . . ?
C15 N1 H2 108.1(19) . . ?
C15 N1 H3 113(2) . . ?
H2 N1 H3 108(3) . . ?
C15 N1 H4 108(2) . . ?
H2 N1 H4 119(3) . . ?
H3 N1 H4 101(3) . . ?
O1 C1 C6 124.85(18) . . ?
O1 C1 C2 114.89(17) . . ?
C6 C1 C2 120.25(18) . . ?
O2 C2 C3 124.75(18) . . ?
O2 C2 C1 115.17(17) . . ?
C3 C2 C1 120.08(17) . . ?
C2 C3 C4 121.28(19) . . ?
C2 C3 Cl1 120.00(16) . . ?
C4 C3 Cl1 118.71(16) . . ?
O3 C4 C3 125.5(2) . . ?
O3 C4 C5 115.85(18) . . ?
C3 C4 C5 118.65(18) . . ?
O4 C5 C6 125.1(2) . . ?
O4 C5 C4 116.46(19) . . ?
C6 C5 C4 118.44(17) . . ?
C1 C6 C5 121.14(19) . . ?
C1 C6 Cl2 119.85(16) . . ?
C5 C6 Cl2 119.01(15) . . ?
O5 C7 C12 124.25(18) . . ?
O5 C7 C8 115.45(16) . . ?
C12 C7 C8 120.29(17) . . ?
O6 C8 C9 125.34(18) . . ?
O6 C8 C7 114.91(17) . . ?
C9 C8 C7 119.75(17) . . ?
C8 C9 C10 122.09(18) . . ?
C8 C9 Cl3 119.47(15) . . ?
C10 C9 Cl3 118.44(15) . . ?
O7 C10 C9 125.41(19) . . ?
O7 C10 C11 116.81(18) . . ?
C9 C10 C11 117.78(17) . . ?
O8 C11 C12 124.32(19) . . ?
O8 C11 C10 117.92(18) . . ?
C12 C11 C10 117.76(17) . . ?
C7 C12 C11 121.96(18) . . ?
C7 C12 Cl4 119.54(15) . . ?
C11 C12 Cl4 118.39(15) . . ?
O9 C13 C14 112.6(3) . . ?
O9 C13 H13A 109.1 . . ?
C14 C13 H13A 109.1 . . ?
O9 C13 H13B 109.1 . . ?
C14 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 C16 112.3(2) . . ?
N1 C15 H15A 109.1 . . ?
C16 C15 H15A 109.1 . . ?
N1 C15 H15B 109.1 . . ?
C16 C15 H15B 109.1 . . ?
H15A C15 H15B 107.9 . . ?
C15 C16 C17 111.4(2) . . ?
C15 C16 H16A 109.3 . . ?
C17 C16 H16A 109.3 . . ?
C15 C16 H16B 109.3 . . ?
C17 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
C18 C17 C16 114.6(2) . . ?
C18 C17 H17A 108.6 . . ?
C16 C17 H17A 108.6 . . ?
C18 C17 H17B 108.6 . . ?
C16 C17 H17B 108.6 . . ?
H17A C17 H17B 107.6 . . ?
C19 C18 C17 113.5(3) . . ?
C19 C18 H18A 108.9 . . ?
C17 C18 H18A 108.9 . . ?
C19 C18 H18B 108.9 . . ?
C17 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
C20 C19 C18 114.9(3) . . ?
C20 C19 H19A 108.6 . . ?
C18 C19 H19A 108.6 . . ?
C20 C19 H19B 108.6 . . ?
C18 C19 H19B 108.6 . . ?
H19A C19 H19B 107.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C21 N2 H2A 109.5 . . ?
C21 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C21 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
N2 C21 C22 110.5(5) . . ?
N2 C21 H21A 109.5 . . ?
C22 C21 H21A 109.5 . . ?
N2 C21 H21B 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 108.1 . . ?
C21 C22 C23 120.5(8) . . ?
C21 C22 H22A 107.2 . . ?
C23 C22 H22A 107.2 . . ?
C21 C22 H22B 107.2 . . ?
C23 C22 H22B 107.2 . . ?
H21A C22 H22B 106.8 . . ?
C24 C23 C22 108.3(14) . . ?
C24 C23 H23A 110.0 . . ?
C22 C23 H23A 110.0 . . ?
C24 C23 H23B 110.0 . . ?
C22 C23 H23B 110.0 . . ?
H23A C23 H23B 108.4 . . ?
C25 C24 C23 120.9(14) . . ?
C25 C24 H24A 107.1 . . ?
C23 C24 H24A 107.1 . . ?
C25 C24 H24B 107.1 . . ?
C23 C24 H24B 107.1 . . ?
H24A C24 H24B 106.8 . . ?
C24 C25 C26 115.7(19) . . ?
C24 C25 H25A 108.3 . . ?
C26 C25 H25A 108.3 . . ?
C24 C25 H25B 108.3 . . ?
C26 C25 H25B 108.3 . . ?
H25A C25 H25B 107.4 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C28 C27 H27A 110.2 . . ?
C28 C27 H27B 110.2 . . ?
H27A C27 H27B 108.5 . . ?
C27 C28 C29 106.0(8) . . ?
C27 C28 H28A 110.5 . . ?
C29 C28 H28A 110.5 . . ?
C27 C28 H28B 110.5 . . ?
C29 C28 H28B 110.5 . . ?
H28A C28 H28B 108.7 . . ?
C30 C29 C28 123.8(14) . . ?
C30 C29 H29A 106.4 . . ?
C28 C29 H29A 106.4 . . ?
C30 C29 H29B 106.4 . . ?
C28 C29 H29B 106.4 . . ?
H29A C29 H29B 106.4 . . ?
C29 C30 C31 131.3(15) . . ?
C29 C30 H30A 104.4 . . ?
C31 C30 H30A 104.4 . . ?
C29 C30 H30B 104.4 . . ?
C31 C30 H30B 104.4 . . ?
H30A C30 H30B 105.6 . . ?
C30 C31 C32 118.8(14) . . ?
C30 C31 H31A 107.6 . . ?
C32 C31 H31A 107.6 . . ?
C30 C31 H31B 107.6 . . ?
C32 C31 H31B 107.6 . . ?
H31A C31 H31B 107.1 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 C1 C6 171.05(17) . . . . ?
Cu1 O1 C1 C2 -8.7(2) . . . . ?
Cu1 O2 C2 C3 -176.54(17) . . . . ?
Cu1 O2 C2 C1 3.9(2) . . . . ?
O1 C1 C2 O2 3.2(3) . . . . ?
C6 C1 C2 O2 -176.54(19) . . . . ?
O1 C1 C2 C3 -176.36(19) . . . . ?
C6 C1 C2 C3 3.9(3) . . . . ?
O2 C2 C3 C4 177.9(2) . . . . ?
C1 C2 C3 C4 -2.6(3) . . . . ?
O2 C2 C3 Cl1 -1.3(3) . . . . ?
C1 C2 C3 Cl1 178.24(15) . . . . ?
C2 C3 C4 O3 179.9(2) . . . . ?
Cl1 C3 C4 O3 -0.9(3) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
Cl1 C3 C4 C5 178.32(15) . . . . ?
O3 C4 C5 O4 2.2(3) . . . . ?
C3 C4 C5 O4 -177.1(2) . . . . ?
O3 C4 C5 C6 -177.4(2) . . . . ?
C3 C4 C5 C6 3.3(3) . . . . ?
O1 C1 C6 C5 178.9(2) . . . . ?
C2 C1 C6 C5 -1.4(3) . . . . ?
O1 C1 C6 Cl2 -1.4(3) . . . . ?
C2 C1 C6 Cl2 178.31(15) . . . . ?
O4 C5 C6 C1 178.3(2) . . . . ?
C4 C5 C6 C1 -2.1(3) . . . . ?
O4 C5 C6 Cl2 -1.4(3) . . . . ?
C4 C5 C6 Cl2 178.26(15) . . . . ?
Cu1 O5 C7 C12 177.06(16) . . . . ?
Cu1 O5 C7 C8 -4.3(2) . . . . ?
Cu1 O6 C8 C9 -174.77(17) . . . . ?
Cu1 O6 C8 C7 4.2(2) . . . . ?
O5 C7 C8 O6 0.1(3) . . . . ?
C12 C7 C8 O6 178.75(18) . . . . ?
O5 C7 C8 C9 179.12(19) . . . . ?
C12 C7 C8 C9 -2.2(3) . . . . ?
O6 C8 C9 C10 -177.9(2) . . . . ?
C7 C8 C9 C10 3.1(3) . . . . ?
O6 C8 C9 Cl3 1.6(3) . . . . ?
C7 C8 C9 Cl3 -177.35(15) . . . . ?
C8 C9 C10 O7 -178.5(2) . . . . ?
Cl3 C9 C10 O7 2.0(3) . . . . ?
C8 C9 C10 C11 0.8(3) . . . . ?
Cl3 C9 C10 C11 -178.74(15) . . . . ?
O7 C10 C11 O8 -6.7(3) . . . . ?
C9 C10 C11 O8 174.0(2) . . . . ?
O7 C10 C11 C12 173.6(2) . . . . ?
C9 C10 C11 C12 -5.8(3) . . . . ?
O5 C7 C12 C11 175.46(19) . . . . ?
C8 C7 C12 C11 -3.1(3) . . . . ?
O5 C7 C12 Cl4 -0.6(3) . . . . ?
C8 C7 C12 Cl4 -179.17(15) . . . . ?
O8 C11 C12 C7 -172.8(2) . . . . ?
C10 C11 C12 C7 6.9(3) . . . . ?
O8 C11 C12 Cl4 3.3(3) . . . . ?
C10 C11 C12 Cl4 -176.99(14) . . . . ?
Cu1 O9 C13 C14 -77.4(4) . . . . ?
N1 C15 C16 C17 173.8(2) . . . . ?
C15 C16 C17 C18 -176.8(2) . . . . ?
C16 C17 C18 C19 178.9(3) . . . . ?
C17 C18 C19 C20 -178.3(3) . . . . ?
N2 C21 C22 C23 -175.0(10) . . . . ?
C21 C22 C23 C24 64.1(19) . . . . ?
C22 C23 C24 C25 140(2) . . . . ?
C23 C24 C25 C26 -118(3) . . . . ?
C27 C28 C29 C30 -101(2) . . . . ?
C28 C29 C30 C31 2(4) . . . . ?
C29 C30 C31 C32 -154(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
C16 H16A Cl4 0.98 2.81 3.572(2) 134.7 .
N2 H2A O5 0.90 1.96 2.855(2) 170.5 .
N2 H2B O3 0.90 2.08 2.928(3) 156.1 1_655
N2 H2B O4 0.90 2.53 3.216(3) 133.9 1_655
N2 H2C O3 0.90 2.34 3.128(3) 146.5 2_566
N2 H2AB O4 0.90 2.10 2.939(3) 155.7 2_566
C22 H22B Cl1 0.98 2.83 3.755(9) 157.8 .
N2A H2C O3 0.90 2.34 3.128(3) 146.5 2_566
N2A H2AB O4 0.90 2.10 2.939(3) 155.7 2_566
N2A H2A O5 0.90 1.96 2.855(2) 170.5 .
N2A H2B O3 0.90 2.08 2.928(3) 156.1 1_655
O9 H1 O3 0.78(3) 1.98(3) 2.743(2) 167(3) 2_566
N1 H2 O7 0.83(3) 2.05(3) 2.856(3) 166(3) 2_756
N1 H2 O8 0.83(3) 2.36(3) 2.819(2) 115(2) 2_756
N1 H3 O1 0.86(3) 1.98(3) 2.830(3) 172(3) 2_656
N1 H4 Cl4 0.89(3) 2.73(3) 3.494(2) 146(3) .
N1 H4 O8 0.89(3) 2.31(3) 3.036(3) 140(3) .

_refine_diff_density_max         0.864
_refine_diff_density_min         -0.752
_refine_diff_density_rms         0.083

####################################################################### 
# 
# 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_ydkr
_database_code_depnum_ccdc_archive 'CCDC 1521428'




_audit_update_record             
;
2017-01-23 deposited with the CCDC.
2017-02-06 downloaded from the CCDC.
;


_diffrn_radiation_source         ?
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         {(Hha)2[Cu(CA)2(EtOH)2]}n
_chemical_formula_sum            'C28 H44 Cl4 Cu N2 O10'
_chemical_formula_weight         773.99

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           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

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

_cell_length_a                   9.8160(16)
_cell_length_b                   16.032(3)
_cell_length_c                   11.2106(17)
_cell_angle_alpha                90
_cell_angle_beta                 91.082(4)
_cell_angle_gamma                90
_cell_volume                     1763.9(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    203(2)
_cell_measurement_reflns_used    9308
_cell_measurement_theta_min      3.02
_cell_measurement_theta_max      27.55

_exptl_crystal_description       platelet
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.457
_exptl_crystal_F_000             806
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.005
_exptl_absorpt_coefficient_mu    0.976
_shelx_estimated_absorpt_T_min   0.829
_shelx_estimated_absorpt_T_max   0.829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.889
_exptl_absorpt_correction_T_max  0.995
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_diffrn_ambient_temperature      203(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Rigaku Saturn70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.143
_diffrn_reflns_number            14701
_diffrn_reflns_av_unetI/netI     0.0410
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.014
_diffrn_reflns_theta_max         27.473
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2098
_reflns_number_gt                1367
_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       PROCESS-AUTO
_computing_cell_refinement       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_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)+(0.0669P)²+1.2162P] 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         2098
_refine_ls_number_parameters     153
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.1002
_refine_ls_R_factor_gt           0.0615
_refine_ls_wR_factor_ref         0.1513
_refine_ls_wR_factor_gt          0.1337
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.122
_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 1.000000 0.000000 1.000000 0.0707(4) Uani 1 4 d S T P . .
Cl1 Cl 0.76054(8) 0.23710(7) 0.80548(8) 0.0777(4) Uani 1 1 d . . . . .
O1 O 0.8983(2) 0.09060(18) 0.9233(2) 0.0702(7) Uani 1 1 d . . . . .
O2 O 0.9009(2) 0.3836(2) 0.9192(2) 0.0826(8) Uani 1 1 d . . . . .
O3 O 0.8429(4) 0.0265(3) 1.1550(4) 0.075(2) Uani 0.5 1 d D . P A -1
H3 H 0.770319 0.051294 1.139987 0.113 Uiso 0.5 1 calc R U P A -1
N1 N 0.6317(4) 0.0143(14) 0.8748(4) 0.053(5) Uani 0.5 1 d D . P B -1
H1A H 0.709339 0.042819 0.888796 0.080 Uiso 0.5 1 calc R U P B -1
H1B H 0.620722 -0.023963 0.932573 0.080 Uiso 0.5 1 calc R U P B -1
H1C H 0.560665 0.049832 0.874267 0.080 Uiso 0.5 1 calc R U P B -1
C1 C 0.9412(3) 0.1621(3) 0.9539(3) 0.0629(10) Uani 1 1 d . . . . .
C2 C 0.8922(3) 0.2370(3) 0.9115(3) 0.0675(11) Uani 1 1 d . . . . .
C3 C 0.9416(3) 0.3146(3) 0.9520(3) 0.0653(10) Uani 1 1 d . . . . .
C4 C 0.8295(11) -0.0216(7) 1.2634(8) 0.099(5) Uani 0.5 1 d D . P A -1
H4A H 0.871805 -0.076764 1.257885 0.119 Uiso 0.5 1 calc R U P A -1
H4B H 0.734450 -0.027131 1.287543 0.119 Uiso 0.5 1 calc R U P A -1
C5 C 0.9091(15) 0.0366(9) 1.3424(10) 0.159(7) Uani 0.5 1 d D . P A -1
H5A H 0.953881 0.078126 1.293888 0.238 Uiso 0.5 1 calc R U P A -1
H5B H 0.977090 0.005312 1.387588 0.238 Uiso 0.5 1 calc R U P A -1
H5C H 0.848009 0.064082 1.396878 0.238 Uiso 0.5 1 calc R U P A -1
C6 C 0.6388(8) -0.0284(5) 0.7567(6) 0.077(3) Uani 0.5 1 d D . P B -1
H6A H 0.711957 -0.070011 0.760216 0.093 Uiso 0.5 1 calc R U P B -1
H6B H 0.552965 -0.058090 0.741412 0.093 Uiso 0.5 1 calc R U P B -1
C7 C 0.6638(7) 0.0290(6) 0.6559(7) 0.091(5) Uani 0.5 1 d D . P B -1
H7A H 0.682622 -0.004386 0.584832 0.110 Uiso 0.5 1 calc R U P B -1
H7B H 0.745597 0.061834 0.674595 0.110 Uiso 0.5 1 calc R U P B -1
C8 C 0.5495(8) 0.0877(5) 0.6265(8) 0.086(3) Uani 0.5 1 d D . P B -1
H8A H 0.467553 0.055037 0.607656 0.103 Uiso 0.5 1 calc R U P B -1
H8B H 0.530765 0.121386 0.697233 0.103 Uiso 0.5 1 calc R U P B -1
C9 C 0.5764(12) 0.1450(8) 0.5244(10) 0.119(4) Uani 0.5 1 d D . P B -1
H9A H 0.584714 0.112390 0.450975 0.143 Uiso 0.5 1 calc R U P B -1
H9B H 0.662619 0.174451 0.538840 0.143 Uiso 0.5 1 calc R U P B -1
C10 C 0.4567(15) 0.2108(10) 0.5085(15) 0.132(5) Uani 0.5 1 d D . P B -1
H10A H 0.375970 0.181587 0.477159 0.159 Uiso 0.5 1 calc R U P B -1
H10B H 0.434205 0.232590 0.587394 0.159 Uiso 0.5 1 calc R U P B -1
C11 C 0.4846(14) 0.2810(9) 0.4305(11) 0.141(5) Uani 0.5 1 d D . P B -1
H11A H 0.569243 0.307471 0.455697 0.212 Uiso 0.5 1 calc R U P B -1
H11B H 0.410749 0.321070 0.434802 0.212 Uiso 0.5 1 calc R U P B -1
H11C H 0.492360 0.261399 0.349102 0.212 Uiso 0.5 1 calc R U P B -1


_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 O1 1.953(3) 2_757 ?
Cu1 O1 1.953(3) 6 ?
Cu1 O1 1.953(3) 5_757 ?
Cu1 O1 1.953(3) . ?
Cl1 C2 1.739(3) . ?
O1 C1 1.267(5) . ?
O2 C3 1.231(5) . ?
O3 C4 1.448(10) . ?
O3 H3 0.8300 . ?
N1 C6 1.494(12) . ?
N1 H1A 0.9000 . ?
N1 H1B 0.9000 . ?
N1 H1C 0.9000 . ?
C1 C2 1.375(6) . ?
C1 C1 1.534(6) 2_757 ?
C2 C3 1.408(6) . ?
C3 C3 1.557(6) 2_757 ?
C4 C5 1.496(12) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 H5C 0.9700 . ?
C6 C7 1.481(9) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C7 C8 1.496(10) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C8 C9 1.494(11) . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C9 C10 1.586(13) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C10 C11 1.455(13) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?

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
O1 Cu1 O1 180.0 2_757 6 ?
O1 Cu1 O1 96.12(15) 2_757 5_757 ?
O1 Cu1 O1 83.88(15) 6 5_757 ?
O1 Cu1 O1 83.88(15) 2_757 . ?
O1 Cu1 O1 96.12(15) 6 . ?
O1 Cu1 O1 180.0 5_757 . ?
C1 O1 Cu1 112.9(2) . . ?
C4 O3 H3 109.5 . . ?
C6 N1 H1A 109.5 . . ?
C6 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C6 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
O1 C1 C2 125.7(3) . . ?
O1 C1 C1 115.12(18) . 2_757 ?
C2 C1 C1 119.1(2) . 2_757 ?
C1 C2 C3 122.9(3) . . ?
C1 C2 Cl1 119.2(3) . . ?
C3 C2 Cl1 117.9(3) . . ?
O2 C3 C2 126.1(3) . . ?
O2 C3 C3 115.96(19) . 2_757 ?
C2 C3 C3 117.9(2) . 2_757 ?
O3 C4 C5 96.3(8) . . ?
O3 C4 H4A 112.5 . . ?
C5 C4 H4A 112.5 . . ?
O3 C4 H4B 112.5 . . ?
C5 C4 H4B 112.5 . . ?
H4A C4 H4B 110.0 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 N1 113.7(9) . . ?
C7 C6 H6A 108.8 . . ?
N1 C6 H6A 108.8 . . ?
C7 C6 H6B 108.8 . . ?
N1 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
C6 C7 C8 115.2(7) . . ?
C6 C7 H7A 108.5 . . ?
C8 C7 H7A 108.5 . . ?
C6 C7 H7B 108.5 . . ?
C8 C7 H7B 108.5 . . ?
H7A C7 H7B 107.5 . . ?
C9 C8 C7 114.4(8) . . ?
C9 C8 H8A 108.7 . . ?
C7 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
C7 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C8 C9 C10 110.7(8) . . ?
C8 C9 H9A 109.5 . . ?
C10 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C11 C10 C9 115.8(9) . . ?
C11 C10 H10A 108.3 . . ?
C9 C10 H10A 108.3 . . ?
C11 C10 H10B 108.3 . . ?
C9 C10 H10B 108.3 . . ?
H10A C10 H10B 107.4 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 C1 C2 177.8(3) . . . . ?
Cu1 O1 C1 C1 -1.8(4) . . . 2_757 ?
O1 C1 C2 C3 178.0(3) . . . . ?
C1 C1 C2 C3 -2.4(6) 2_757 . . . ?
O1 C1 C2 Cl1 -0.5(5) . . . . ?
C1 C1 C2 Cl1 179.1(3) 2_757 . . . ?
C1 C2 C3 O2 -178.8(3) . . . . ?
Cl1 C2 C3 O2 -0.3(5) . . . . ?
C1 C2 C3 C3 0.8(6) . . . 2_757 ?
Cl1 C2 C3 C3 179.3(3) . . . 2_757 ?
N1 C6 C7 C8 -67.9(9) . . . . ?
C6 C7 C8 C9 -179.9(8) . . . . ?
C7 C8 C9 C10 -174.2(10) . . . . ?
C8 C9 C10 C11 166.8(14) . . . . ?

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
N1 H1A O1 0.90 2.04 2.931(11) 171.6 .
N1 H1B O2 0.90 2.62 3.132(16) 117.0 3_445
N1 H1B O2 0.90 2.24 3.139(16) 177.8 4_647
N1 H1C O2 0.90 1.97 2.846(14) 164.0 8_455
C6 H6A Cl1 0.98 2.77 3.591(7) 142.2 6
C6 H6A O1 0.98 2.58 3.285(7) 128.6 6

_refine_diff_density_max         0.557
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.054

####################################################################### 
# 
# 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_ydkr
_database_code_depnum_ccdc_archive 'CCDC 1521434'
#Added by publCIF



_audit_update_record             
;
2017-01-23 deposited with the CCDC.
2017-02-06 downloaded from the CCDC.
;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         {(Hha)2[Cu(CA)2(EtOH)2]}n
_chemical_formula_sum            'C28 H44 Cl4 Cu N2 O10'
_chemical_formula_weight         773.99

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           12
_space_group_name_H-M_alt        'C 2/m'
_space_group_name_Hall           '-C 2y'

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

_cell_length_a                   9.7962(4)
_cell_length_b                   16.0447(8)
_cell_length_c                   11.0491(5)
_cell_angle_alpha                90
_cell_angle_beta                 90.9641(14)
_cell_angle_gamma                90
_cell_volume                     1736.42(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11347
_cell_measurement_theta_min      3.04
_cell_measurement_theta_max      27.51

_exptl_crystal_description       platelet
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.480
_exptl_crystal_F_000             806
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.991
_shelx_estimated_absorpt_T_min   0.888
_shelx_estimated_absorpt_T_max   0.952
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.619
_exptl_absorpt_correction_T_max  0.952
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku Saturn70'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.143
_diffrn_reflns_number            14525
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_av_R_equivalents  0.0707
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.035
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2064
_reflns_number_gt                1415
_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       PROCESS-AUTO
_computing_cell_refinement       PROCESS-AUTO
_computing_data_reduction        PROCESS-AUTO
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_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)+(0.0950P)²+1.6347P] 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         2064
_refine_ls_number_parameters     153
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0579
_refine_ls_wR_factor_ref         0.1705
_refine_ls_wR_factor_gt          0.1506
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.053
_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 0.500000 0.500000 0.500000 0.0601(4) Uani 1 4 d S T P . .
Cl1 Cl 0.25938(8) 0.26240(7) 0.30292(7) 0.0662(4) Uani 1 1 d . . . . .
O1 O 0.3984(2) 0.40883(18) 0.4215(2) 0.0610(7) Uani 1 1 d . . . . .
O2 O 0.4003(2) 0.1158(2) 0.4177(2) 0.0701(8) Uani 1 1 d . . . . .
O3 O 0.3416(4) 0.4756(3) 0.6543(4) 0.064(3) Uani 0.5 1 d D . P A -1
H3 H 0.268977 0.449627 0.638683 0.097 Uiso 0.5 1 calc R U P A -1
N1 N 0.1327(4) 0.4859(12) 0.3749(4) 0.042(4) Uani 0.5 1 d D . P B -1
H1A H 0.064010 0.447784 0.372859 0.063 Uiso 0.5 1 calc R U P B -1
H1B H 0.115727 0.524683 0.432933 0.063 Uiso 0.5 1 calc R U P B -1
H1C H 0.213163 0.459854 0.392370 0.063 Uiso 0.5 1 calc R U P B -1
C1 C 0.4411(3) 0.3372(3) 0.4531(3) 0.0574(10) Uani 1 1 d . . . . .
C2 C 0.3917(3) 0.2621(3) 0.4100(3) 0.0594(10) Uani 1 1 d . . . . .
C3 C 0.4414(3) 0.1850(3) 0.4514(3) 0.0579(10) Uani 1 1 d . . . . .
C4 C 0.3268(9) 0.5213(4) 0.7638(7) 0.068(3) Uani 0.5 1 d D . P A -1
H4A H 0.230138 0.527069 0.787035 0.081 Uiso 0.5 1 calc R U P A -1
H4B H 0.370185 0.577005 0.760006 0.081 Uiso 0.5 1 calc R U P A -1
C5 C 0.4073(13) 0.4602(7) 0.8482(8) 0.107(4) Uani 0.5 1 d D . P A -1
H5A H 0.370843 0.403740 0.837972 0.160 Uiso 0.5 1 calc R U P . .
H5B H 0.397690 0.477718 0.932561 0.160 Uiso 0.5 1 calc R U P . .
H5C H 0.504082 0.460776 0.827014 0.160 Uiso 0.5 1 calc R U P . .
C6 C 0.1414(8) 0.5280(5) 0.2541(6) 0.066(3) Uani 0.5 1 d D . P B -1
H6A H 0.055400 0.558786 0.238312 0.080 Uiso 0.5 1 calc R U P B -1
H6B H 0.216544 0.569250 0.257503 0.080 Uiso 0.5 1 calc R U P B -1
C7 C 0.1652(7) 0.4701(6) 0.1516(7) 0.081(4) Uani 0.5 1 d D . P B -1
H7A H 0.248366 0.437084 0.170060 0.097 Uiso 0.5 1 calc R U P B -1
H7B H 0.183359 0.503575 0.078377 0.097 Uiso 0.5 1 calc R U P B -1
C8 C 0.0515(8) 0.4113(6) 0.1231(8) 0.076(2) Uani 0.5 1 d D . P B -1
H8A H -0.031802 0.444334 0.105247 0.091 Uiso 0.5 1 calc R U P B -1
H8B H 0.033708 0.377630 0.196246 0.091 Uiso 0.5 1 calc R U P B -1
C9 C 0.0743(11) 0.3525(7) 0.0186(9) 0.099(4) Uani 0.5 1 d D . P B -1
H9A H 0.071414 0.384402 -0.058139 0.118 Uiso 0.5 1 calc R U P B -1
H9B H 0.165971 0.327067 0.027179 0.118 Uiso 0.5 1 calc R U P B -1
C10 C -0.0316(16) 0.2847(8) 0.0131(12) 0.118(5) Uani 0.5 1 d D . P B -1
H10A H -0.037777 0.260538 0.095238 0.142 Uiso 0.5 1 calc R U P B -1
H10B H -0.120643 0.311492 -0.005301 0.142 Uiso 0.5 1 calc R U P B -1
C11 C -0.0163(11) 0.2161(7) -0.0710(10) 0.099(3) Uani 0.5 1 d D . P B -1
H11A H -0.005670 0.238063 -0.153055 0.148 Uiso 0.5 1 calc R U P B -1
H11B H -0.097472 0.180451 -0.068655 0.148 Uiso 0.5 1 calc R U P B -1
H11C H 0.064557 0.183376 -0.048102 0.148 Uiso 0.5 1 calc R U P B -1


_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 O1 1.963(3) . ?
Cu1 O1 1.963(3) 6_565 ?
Cu1 O1 1.963(3) 5_666 ?
Cu1 O1 1.963(3) 2_656 ?
Cl1 C2 1.741(3) . ?
O1 C1 1.270(5) . ?
O2 C3 1.235(5) . ?
O3 C4 1.423(8) . ?
O3 H3 0.8400 . ?
N1 C6 1.499(11) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
C1 C2 1.380(6) . ?
C1 C1 1.539(6) 2_656 ?
C2 C3 1.403(6) . ?
C3 C3 1.559(6) 2_656 ?
C4 C5 1.558(10) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.487(10) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.489(10) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.510(11) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.504(13) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.450(12) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 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
O1 Cu1 O1 96.35(14) . 6_565 ?
O1 Cu1 O1 180.0 . 5_666 ?
O1 Cu1 O1 83.65(14) 6_565 5_666 ?
O1 Cu1 O1 83.65(14) . 2_656 ?
O1 Cu1 O1 180.0 6_565 2_656 ?
O1 Cu1 O1 96.35(14) 5_666 2_656 ?
C1 O1 Cu1 113.03(19) . . ?
C4 O3 H3 109.5 . . ?
C6 N1 H1A 109.5 . . ?
C6 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C6 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
O1 C1 C2 125.7(3) . . ?
O1 C1 C1 115.13(18) . 2_656 ?
C2 C1 C1 119.1(2) . 2_656 ?
C1 C2 C3 122.7(3) . . ?
C1 C2 Cl1 119.0(3) . . ?
C3 C2 Cl1 118.3(3) . . ?
O2 C3 C2 125.8(3) . . ?
O2 C3 C3 116.09(18) . 2_656 ?
C2 C3 C3 118.1(2) . 2_656 ?
O3 C4 C5 97.3(6) . . ?
O3 C4 H4A 112.3 . . ?
C5 C4 H4A 112.3 . . ?
O3 C4 H4B 112.3 . . ?
C5 C4 H4B 112.3 . . ?
H4A C4 H4B 109.9 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 N1 114.2(9) . . ?
C7 C6 H6A 108.7 . . ?
N1 C6 H6A 108.7 . . ?
C7 C6 H6B 108.7 . . ?
N1 C6 H6B 108.7 . . ?
H6A C6 H6B 107.6 . . ?
C6 C7 C8 115.5(7) . . ?
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 . . ?
C7 C8 C9 115.9(8) . . ?
C7 C8 H8A 108.3 . . ?
C9 C8 H8A 108.3 . . ?
C7 C8 H8B 108.3 . . ?
C9 C8 H8B 108.3 . . ?
H8A C8 H8B 107.4 . . ?
C10 C9 C8 111.8(8) . . ?
C10 C9 H9A 109.2 . . ?
C8 C9 H9A 109.2 . . ?
C10 C9 H9B 109.2 . . ?
C8 C9 H9B 109.2 . . ?
H9A C9 H9B 107.9 . . ?
C11 C10 C9 119.8(8) . . ?
C11 C10 H10A 107.4 . . ?
C9 C10 H10A 107.4 . . ?
C11 C10 H10B 107.4 . . ?
C9 C10 H10B 107.4 . . ?
H10A C10 H10B 106.9 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 C1 C2 -178.1(3) . . . . ?
Cu1 O1 C1 C1 1.4(4) . . . 2_656 ?
O1 C1 C2 C3 -178.3(3) . . . . ?
C1 C1 C2 C3 2.2(6) 2_656 . . . ?
O1 C1 C2 Cl1 0.0(5) . . . . ?
C1 C1 C2 Cl1 -179.5(3) 2_656 . . . ?
C1 C2 C3 O2 179.0(3) . . . . ?
Cl1 C2 C3 O2 0.6(5) . . . . ?
C1 C2 C3 C3 -0.9(6) . . . 2_656 ?
Cl1 C2 C3 C3 -179.2(3) . . . 2_656 ?
N1 C6 C7 C8 66.6(9) . . . . ?
C6 C7 C8 C9 179.7(7) . . . . ?
C7 C8 C9 C10 168.2(10) . . . . ?
C8 C9 C10 C11 -171.8(12) . . . . ?

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
N1 H1A O2 0.91 1.97 2.848(12) 161.2 8_455
N1 H1B O2 0.91 2.57 3.128(14) 120.2 3_455
N1 H1B O2 0.91 2.21 3.118(14) 173.1 4_556
N1 H1C O1 0.91 2.01 2.920(9) 175.3 .
C6 H6B Cl1 0.99 2.78 3.594(7) 140.1 6_565
C6 H6B O1 0.99 2.54 3.260(7) 129.1 6_565

_refine_diff_density_max         1.012
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.079

####################################################################### 
# 
# 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_ydkr
_database_code_depnum_ccdc_archive 'CCDC 1521430'
#Added by publCIF



_audit_update_record             
;
2017-01-23 deposited with the CCDC.
2017-02-06 downloaded from the CCDC.
;
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         {(Hha)2[Cu(CA)2(EtOH)]}n
_chemical_formula_sum            'C26 H38 Cl4 Cu N2 O9'
_chemical_formula_weight         727.92

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

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

_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                   10.064(5)
_cell_length_b                   12.559(6)
_cell_length_c                   14.362(7)
_cell_angle_alpha                69.311(8)
_cell_angle_beta                 88.594(7)
_cell_angle_gamma                86.781(7)
_cell_volume                     1695.6(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1574
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      27.25

_exptl_crystal_description       block
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_F_000             754
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    1.008
_shelx_estimated_absorpt_T_min   0.689
_shelx_estimated_absorpt_T_max   0.863
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.785
_exptl_absorpt_correction_T_max  0.860
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16372
_diffrn_reflns_av_unetI/netI     0.0633
_diffrn_reflns_av_R_equivalents  0.0463
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.032
_diffrn_reflns_theta_max         27.350
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             7601
_reflns_number_gt                4746
_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       'RAPID AUTO (Rigaku, 2011)'
_computing_cell_refinement       'RAPID AUTO (Rigaku, 2011)'
_computing_data_reduction        'RAPID AUTO (Rigaku, 2011)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_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)+(0.0898P)²] 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         7601
_refine_ls_number_parameters     417
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0559
_refine_ls_wR_factor_ref         0.1714
_refine_ls_wR_factor_gt          0.1495
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.047
_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 0.74054(3) 0.22992(3) -0.07775(3) 0.04875(16) Uani 1 1 d . . . . .
Cl1 Cl 0.49268(9) 0.38010(8) 0.15978(7) 0.0575(2) Uani 1 1 d . . . . .
Cl2 Cl 0.29825(8) 0.31655(8) -0.23717(7) 0.0575(2) Uani 1 1 d . . . . .
Cl3 Cl 0.99064(8) 0.06533(8) -0.30247(7) 0.0595(3) Uani 1 1 d . . . . .
Cl4 Cl 1.17773(7) 0.13924(6) 0.09103(6) 0.0472(2) Uani 1 1 d . . . . .
O1 O 0.56399(19) 0.24703(19) -0.13553(18) 0.0495(6) Uani 1 1 d . . . . .
O2 O 0.6480(2) 0.2841(2) 0.02127(18) 0.0525(6) Uani 1 1 d . . . . .
O3 O 0.2216(2) 0.4427(2) 0.0637(2) 0.0619(7) Uani 1 1 d . . . . .
O4 O 0.1452(2) 0.4243(2) -0.1058(2) 0.0662(7) Uani 1 1 d . . . . .
O5 O 0.90907(19) 0.19193(18) -0.00552(17) 0.0474(5) Uani 1 1 d . . . . .
O6 O 0.82834(19) 0.15737(18) -0.16427(17) 0.0469(5) Uani 1 1 d . . . . .
O7 O 1.2622(2) 0.0095(2) -0.20608(19) 0.0580(6) Uani 1 1 d . . . . .
O8 O 1.3329(2) 0.0224(2) -0.02976(18) 0.0540(6) Uani 1 1 d . . . . .
O9 O 0.7920(3) 0.4119(2) -0.1708(2) 0.0753(8) Uani 1 1 d . . . . .
N1 N 1.4635(3) -0.0419(3) 0.1753(3) 0.0519(7) Uani 1 1 d . . . . .
C1 C 0.4768(3) 0.2974(2) -0.0945(2) 0.0418(7) Uani 1 1 d . . . . .
C2 C 0.5250(3) 0.3159(2) -0.0020(2) 0.0427(7) Uani 1 1 d . . . . .
C3 C 0.4392(3) 0.3626(3) 0.0523(3) 0.0440(7) Uani 1 1 d . . . . .
C4 C 0.3065(3) 0.3993(2) 0.0200(3) 0.0476(8) Uani 1 1 d . . . . .
C5 C 0.2601(3) 0.3867(2) -0.0778(3) 0.0469(8) Uani 1 1 d . . . . .
C6 C 0.3505(3) 0.3340(2) -0.1295(2) 0.0432(7) Uani 1 1 d . . . . .
C7 C 0.9991(3) 0.1480(2) -0.0495(2) 0.0401(7) Uani 1 1 d . . . . .
C8 C 0.9537(3) 0.1273(2) -0.1411(2) 0.0406(7) Uani 1 1 d . . . . .
C9 C 1.0418(3) 0.0820(3) -0.1939(2) 0.0438(7) Uani 1 1 d . . . . .
C10 C 1.1765(3) 0.0487(3) -0.1620(3) 0.0440(7) Uani 1 1 d . . . . .
C11 C 1.2196(3) 0.0614(2) -0.0634(2) 0.0424(7) Uani 1 1 d . . . . .
C12 C 1.1276(3) 0.1170(2) -0.0153(2) 0.0409(7) Uani 1 1 d . . . . .
C13 C 0.7948(7) 0.4628(5) -0.2763(5) 0.118(2) Uani 1 1 d . . . . .
H13A H 0.791900 0.544930 -0.294252 0.141 Uiso 1 1 calc R U . . .
H13B H 0.715448 0.443549 -0.302649 0.141 Uiso 1 1 calc R U . . .
C14 C 0.9085(9) 0.4290(6) -0.3222(5) 0.160(3) Uani 1 1 d . . . . .
H14A H 0.903231 0.466710 -0.393013 0.192 Uiso 1 1 calc R U . . .
H14B H 0.987634 0.449501 -0.298014 0.192 Uiso 1 1 calc R U . . .
H14C H 0.911077 0.347982 -0.306422 0.192 Uiso 1 1 calc R U . . .
C15 C 1.4077(3) -0.0514(3) 0.2744(3) 0.0557(9) Uani 1 1 d . . . . .
H15A H 1.457259 -0.111406 0.325510 0.067 Uiso 1 1 calc R U . . .
H15B H 1.315943 -0.072630 0.278083 0.067 Uiso 1 1 calc R U . . .
C16 C 1.4129(4) 0.0590(3) 0.2944(3) 0.0626(10) Uani 1 1 d . . . . .
H16A H 1.372328 0.120860 0.239407 0.075 Uiso 1 1 calc R U . . .
H16B H 1.505024 0.075580 0.298787 0.075 Uiso 1 1 calc R U . . .
C17 C 1.3402(5) 0.0521(4) 0.3913(3) 0.0808(12) Uani 1 1 d . . . . .
H17A H 1.249859 0.030731 0.387697 0.097 Uiso 1 1 calc R U . . .
H17B H 1.383772 -0.008051 0.445983 0.097 Uiso 1 1 calc R U . . .
C18 C 1.3346(5) 0.1602(4) 0.4144(4) 0.0894(14) Uani 1 1 d . . . . .
H18A H 1.292923 0.220999 0.359169 0.107 Uiso 1 1 calc R U . . .
H18B H 1.424860 0.180650 0.419993 0.107 Uiso 1 1 calc R U . . .
C19 C 1.2594(6) 0.1523(5) 0.5091(4) 0.1060(17) Uani 1 1 d . . . . .
H19A H 1.169470 0.131182 0.503518 0.127 Uiso 1 1 calc R U . . .
H19B H 1.301491 0.091653 0.564189 0.127 Uiso 1 1 calc R U . . .
C20 C 1.2521(7) 0.2574(5) 0.5327(5) 0.122(2) Uani 1 1 d . . . . .
H20A H 1.202940 0.244880 0.593504 0.147 Uiso 1 1 calc R U . . .
H20B H 1.340404 0.278170 0.540447 0.147 Uiso 1 1 calc R U . . .
H20C H 1.208130 0.317774 0.479660 0.147 Uiso 1 1 calc R U . . .
N2 N 0.9495(3) 0.3551(3) 0.0874(3) 0.0669(9) Uani 0.5 1 d . . P . .
H2A H 0.932331 0.300071 0.064581 0.100 Uiso 0.5 1 calc R U P . .
H2B H 1.025242 0.386005 0.060864 0.100 Uiso 0.5 1 calc R U P . .
H2C H 0.883371 0.408386 0.070953 0.100 Uiso 0.5 1 calc R U P . .
C21 C 0.9621(9) 0.3060(9) 0.1986(8) 0.077(2) Uani 0.5 1 d D . P . .
H21A H 0.986095 0.365224 0.222893 0.092 Uiso 0.5 1 calc R U P . .
H21B H 1.032710 0.246719 0.216384 0.092 Uiso 0.5 1 calc R U P . .
C22 C 0.8343(13) 0.2570(13) 0.2476(10) 0.124(3) Uani 0.5 1 d D . P . .
H22A H 0.765949 0.318059 0.226295 0.149 Uiso 0.5 1 calc R U P . .
H22B H 0.811837 0.200744 0.219334 0.149 Uiso 0.5 1 calc R U P . .
C23 C 0.820(3) 0.202(2) 0.3588(14) 0.142(8) Uani 0.5 1 d D . P . .
H23A H 0.734765 0.167077 0.371438 0.171 Uiso 0.5 1 calc R U P . .
H23B H 0.887822 0.140241 0.380399 0.171 Uiso 0.5 1 calc R U P . .
C24 C 0.829(2) 0.269(2) 0.4261(15) 0.190(6) Uani 0.5 1 d D . P . .
H24A H 0.817105 0.220200 0.494861 0.228 Uiso 0.5 1 calc R U P . .
H24B H 0.915129 0.301662 0.419363 0.228 Uiso 0.5 1 calc R U P . .
C25 C 0.723(4) 0.361(2) 0.3989(19) 0.258(10) Uani 0.5 1 d D . P . .
H25A H 0.649410 0.338128 0.369708 0.310 Uiso 0.5 1 calc R U P . .
H25B H 0.757736 0.428841 0.349076 0.310 Uiso 0.5 1 calc R U P . .
C26 C 0.674(5) 0.390(6) 0.487(3) 0.232(14) Uani 0.5 1 d D . P . .
H26A H 0.647976 0.322536 0.538614 0.348 Uiso 0.5 1 calc R U P . .
H26B H 0.599180 0.444092 0.467223 0.348 Uiso 0.5 1 calc R U P . .
H26C H 0.743921 0.423443 0.510125 0.348 Uiso 0.5 1 calc R U P . .
N2A N 0.9495(3) 0.3551(3) 0.0874(3) 0.0669(9) Uani 0.5 1 d . . P A 1
H2AA H 0.929106 0.331144 0.038425 0.100 Uiso 0.5 1 calc R U P A 1
H2AB H 1.037511 0.352611 0.093407 0.100 Uiso 0.5 1 calc R U P A 1
H2AC H 0.917124 0.426395 0.073734 0.100 Uiso 0.5 1 calc R U P A 1
C27 C 0.8856(10) 0.2741(9) 0.1900(8) 0.077(2) Uani 0.5 1 d D . P A 1
H27A H 0.790184 0.289700 0.190569 0.092 Uiso 0.5 1 calc R U P A 1
H27B H 0.902565 0.194663 0.197844 0.092 Uiso 0.5 1 calc R U P A 1
C28 C 0.9466(13) 0.2981(12) 0.2683(9) 0.124(3) Uani 0.5 1 d D . P A 1
H28A H 0.932441 0.378115 0.259379 0.149 Uiso 0.5 1 calc R U P A 1
H28B H 1.041562 0.279648 0.269623 0.149 Uiso 0.5 1 calc R U P A 1
C29 C 0.881(2) 0.224(2) 0.3645(15) 0.142(8) Uani 0.5 1 d D . P A 1
H29A H 0.856963 0.153167 0.358392 0.171 Uiso 0.5 1 calc R U P A 1
H29B H 0.943122 0.206167 0.419194 0.171 Uiso 0.5 1 calc R U P A 1
C30 C 0.760(2) 0.286(3) 0.3851(15) 0.190(6) Uani 0.5 1 d D . P A 1
H30A H 0.758389 0.360712 0.333190 0.228 Uiso 0.5 1 calc R U P A 1
H30B H 0.685617 0.247713 0.371649 0.228 Uiso 0.5 1 calc R U P A 1
C31 C 0.725(3) 0.306(2) 0.4723(15) 0.258(10) Uani 0.5 1 d D . P A 1
H31A H 0.804291 0.326892 0.497991 0.310 Uiso 0.5 1 calc R U P A 1
H31B H 0.696873 0.235546 0.521345 0.310 Uiso 0.5 1 calc R U P A 1
C32 C 0.619(5) 0.396(6) 0.462(3) 0.232(14) Uani 0.5 1 d D . P A 1
H32A H 0.549226 0.388466 0.420318 0.348 Uiso 0.5 1 calc R U P A 1
H32B H 0.655075 0.469927 0.431710 0.348 Uiso 0.5 1 calc R U P A 1
H32C H 0.582988 0.389057 0.526112 0.348 Uiso 0.5 1 calc R U P A 1
H1 H 0.780(5) 0.465(4) -0.135(4) 0.117(17) Uiso 1 1 d . . . . .
H2 H 1.549(4) -0.016(3) 0.169(3) 0.071(12) Uiso 1 1 d . . . . .
H3 H 1.462(3) -0.103(3) 0.166(2) 0.044(9) Uiso 1 1 d . . . . .
H4 H 1.413(4) -0.003(3) 0.130(3) 0.080(15) 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 O1 1.948(2) . ?
Cu1 O6 1.952(2) . ?
Cu1 O5 1.956(2) . ?
Cu1 O2 1.975(2) . ?
Cu1 O9 2.284(3) . ?
Cl1 C3 1.737(3) . ?
Cl2 C6 1.735(3) . ?
Cl3 C9 1.738(3) . ?
Cl4 C12 1.738(3) . ?
O1 C1 1.301(3) . ?
O2 C2 1.294(3) . ?
O3 C4 1.259(4) . ?
O4 C5 1.245(4) . ?
O5 C7 1.298(3) . ?
O6 C8 1.313(3) . ?
O7 C10 1.239(3) . ?
O8 C11 1.254(4) . ?
O9 C13 1.421(6) . ?
O9 H1 0.98(5) . ?
N1 C15 1.484(5) . ?
N1 H2 0.93(4) . ?
N1 H3 0.82(3) . ?
N1 H4 0.83(4) . ?
C1 C6 1.372(4) . ?
C1 C2 1.521(4) . ?
C2 C3 1.390(4) . ?
C3 C4 1.422(4) . ?
C4 C5 1.553(5) . ?
C5 C6 1.436(4) . ?
C7 C12 1.380(4) . ?
C7 C8 1.514(4) . ?
C8 C9 1.379(4) . ?
C9 C10 1.433(4) . ?
C10 C11 1.554(5) . ?
C11 C12 1.434(4) . ?
C13 C14 1.424(8) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.517(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.533(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.505(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.515(6) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.473(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
N2 C21 1.500(11) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N2 H2C 0.8900 . ?
C21 C22 1.506(13) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.506(17) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 C24 1.502(17) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.474(17) . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C25 C26 1.50(2) . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 C28 1.422(12) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 C29 1.524(16) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 C30 1.489(18) . ?
C29 H29A 0.9700 . ?
C29 H29B 0.9700 . ?
C30 C31 1.395(16) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 C32 1.49(2) . ?
C31 H31A 0.9700 . ?
C31 H31B 0.9700 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?

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
O1 Cu1 O6 96.40(9) . . ?
O1 Cu1 O5 171.62(9) . . ?
O6 Cu1 O5 84.28(9) . . ?
O1 Cu1 O2 83.92(9) . . ?
O6 Cu1 O2 172.92(9) . . ?
O5 Cu1 O2 94.37(9) . . ?
O1 Cu1 O9 93.43(11) . . ?
O6 Cu1 O9 96.36(11) . . ?
O5 Cu1 O9 94.80(10) . . ?
O2 Cu1 O9 90.68(11) . . ?
C1 O1 Cu1 112.85(19) . . ?
C2 O2 Cu1 112.2(2) . . ?
C7 O5 Cu1 112.46(19) . . ?
C8 O6 Cu1 112.69(19) . . ?
C13 O9 Cu1 127.5(3) . . ?
C13 O9 H1 116(3) . . ?
Cu1 O9 H1 113(3) . . ?
C15 N1 H2 110(2) . . ?
C15 N1 H3 111(2) . . ?
H2 N1 H3 111(3) . . ?
C15 N1 H4 111(3) . . ?
H2 N1 H4 113(4) . . ?
H3 N1 H4 99(4) . . ?
O1 C1 C6 124.8(3) . . ?
O1 C1 C2 114.9(2) . . ?
C6 C1 C2 120.3(3) . . ?
O2 C2 C3 124.0(3) . . ?
O2 C2 C1 115.3(2) . . ?
C3 C2 C1 120.6(3) . . ?
C2 C3 C4 120.8(3) . . ?
C2 C3 Cl1 120.7(2) . . ?
C4 C3 Cl1 118.5(2) . . ?
O3 C4 C3 125.6(3) . . ?
O3 C4 C5 116.1(3) . . ?
C3 C4 C5 118.4(3) . . ?
O4 C5 C6 124.6(3) . . ?
O4 C5 C4 116.5(3) . . ?
C6 C5 C4 118.9(2) . . ?
C1 C6 C5 120.8(3) . . ?
C1 C6 Cl2 119.9(2) . . ?
C5 C6 Cl2 119.3(2) . . ?
O5 C7 C12 123.9(3) . . ?
O5 C7 C8 115.7(2) . . ?
C12 C7 C8 120.3(3) . . ?
O6 C8 C9 125.1(3) . . ?
O6 C8 C7 114.5(2) . . ?
C9 C8 C7 120.4(2) . . ?
C8 C9 C10 121.5(3) . . ?
C8 C9 Cl3 119.9(2) . . ?
C10 C9 Cl3 118.6(2) . . ?
O7 C10 C9 125.4(3) . . ?
O7 C10 C11 116.7(3) . . ?
C9 C10 C11 117.9(2) . . ?
O8 C11 C12 123.3(3) . . ?
O8 C11 C10 118.3(2) . . ?
C12 C11 C10 118.4(2) . . ?
C7 C12 C11 121.1(3) . . ?
C7 C12 Cl4 119.9(2) . . ?
C11 C12 Cl4 118.9(2) . . ?
O9 C13 C14 114.4(6) . . ?
O9 C13 H13A 108.7 . . ?
C14 C13 H13A 108.7 . . ?
O9 C13 H13B 108.7 . . ?
C14 C13 H13B 108.7 . . ?
H13A C13 H13B 107.6 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 C16 112.3(3) . . ?
N1 C15 H15A 109.1 . . ?
C16 C15 H15A 109.1 . . ?
N1 C15 H15B 109.1 . . ?
C16 C15 H15B 109.1 . . ?
H15A C15 H15B 107.9 . . ?
C15 C16 C17 111.6(3) . . ?
C15 C16 H16A 109.3 . . ?
C17 C16 H16A 109.3 . . ?
C15 C16 H16B 109.3 . . ?
C17 C16 H16B 109.3 . . ?
H16A C16 H16B 108.0 . . ?
C18 C17 C16 115.1(4) . . ?
C18 C17 H17A 108.5 . . ?
C16 C17 H17A 108.5 . . ?
C18 C17 H17B 108.5 . . ?
C16 C17 H17B 108.5 . . ?
H17A C17 H17B 107.5 . . ?
C17 C18 C19 114.2(4) . . ?
C17 C18 H18A 108.7 . . ?
C19 C18 H18A 108.7 . . ?
C17 C18 H18B 108.7 . . ?
C19 C18 H18B 108.7 . . ?
H18A C18 H18B 107.6 . . ?
C20 C19 C18 115.0(5) . . ?
C20 C19 H19A 108.5 . . ?
C18 C19 H19A 108.5 . . ?
C20 C19 H19B 108.5 . . ?
C18 C19 H19B 108.5 . . ?
H19A C19 H19B 107.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C21 N2 H2A 109.5 . . ?
C21 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C21 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
N2 C21 C22 111.6(9) . . ?
N2 C21 H21A 109.3 . . ?
C22 C21 H21A 109.3 . . ?
N2 C21 H21B 109.3 . . ?
C22 C21 H21B 109.3 . . ?
H21A C21 H21B 108.0 . . ?
C23 C22 C21 122.5(14) . . ?
C23 C22 H22A 106.7 . . ?
C21 C22 H22A 106.7 . . ?
C23 C22 H22B 106.7 . . ?
C21 C22 H22B 106.7 . . ?
H22A C22 H22B 106.6 . . ?
C24 C23 C22 121.4(19) . . ?
C24 C23 H23A 107.0 . . ?
C22 C23 H23A 107.0 . . ?
C24 C23 H23B 107.0 . . ?
C22 C23 H23B 107.0 . . ?
H23A C23 H23B 106.7 . . ?
C25 C24 C23 109(2) . . ?
C25 C24 H24A 109.9 . . ?
C23 C24 H24A 109.9 . . ?
C25 C24 H24B 109.9 . . ?
C23 C24 H24B 109.9 . . ?
H24A C24 H24B 108.3 . . ?
C24 C25 C26 112(2) . . ?
C24 C25 H25A 109.2 . . ?
C26 C25 H25A 109.2 . . ?
C24 C25 H25B 109.2 . . ?
C26 C25 H25B 109.2 . . ?
H25A C25 H25B 107.9 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C28 C27 H27A 110.3 . . ?
C28 C27 H27B 110.3 . . ?
H27A C27 H27B 108.6 . . ?
C27 C28 C29 106.3(13) . . ?
C27 C28 H28A 110.5 . . ?
C29 C28 H28A 110.5 . . ?
C27 C28 H28B 110.5 . . ?
C29 C28 H28B 110.5 . . ?
H28A C28 H28B 108.7 . . ?
C30 C29 C28 109.6(19) . . ?
C30 C29 H29A 109.8 . . ?
C28 C29 H29A 109.8 . . ?
C30 C29 H29B 109.8 . . ?
C28 C29 H29B 109.8 . . ?
H29A C29 H29B 108.2 . . ?
C31 C30 C29 128(2) . . ?
C31 C30 H30A 105.2 . . ?
C29 C30 H30A 105.2 . . ?
C31 C30 H30B 105.2 . . ?
C29 C30 H30B 105.2 . . ?
H30A C30 H30B 105.9 . . ?
C30 C31 C32 115(3) . . ?
C30 C31 H31A 108.4 . . ?
C32 C31 H31A 108.4 . . ?
C30 C31 H31B 108.4 . . ?
C32 C31 H31B 108.4 . . ?
H31A C31 H31B 107.5 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 C1 C6 170.6(3) . . . . ?
Cu1 O1 C1 C2 -8.5(3) . . . . ?
Cu1 O2 C2 C3 -176.8(2) . . . . ?
Cu1 O2 C2 C1 4.0(3) . . . . ?
O1 C1 C2 O2 3.0(4) . . . . ?
C6 C1 C2 O2 -176.2(3) . . . . ?
O1 C1 C2 C3 -176.2(3) . . . . ?
C6 C1 C2 C3 4.7(4) . . . . ?
O2 C2 C3 C4 177.8(3) . . . . ?
C1 C2 C3 C4 -3.2(5) . . . . ?
O2 C2 C3 Cl1 -0.9(5) . . . . ?
C1 C2 C3 Cl1 178.2(2) . . . . ?
C2 C3 C4 O3 -179.8(3) . . . . ?
Cl1 C3 C4 O3 -1.1(5) . . . . ?
C2 C3 C4 C5 -0.4(4) . . . . ?
Cl1 C3 C4 C5 178.3(2) . . . . ?
O3 C4 C5 O4 2.5(4) . . . . ?
C3 C4 C5 O4 -177.0(3) . . . . ?
O3 C4 C5 C6 -177.8(3) . . . . ?
C3 C4 C5 C6 2.8(4) . . . . ?
O1 C1 C6 C5 178.7(3) . . . . ?
C2 C1 C6 C5 -2.3(5) . . . . ?
O1 C1 C6 Cl2 -1.1(5) . . . . ?
C2 C1 C6 Cl2 177.9(2) . . . . ?
O4 C5 C6 C1 178.4(3) . . . . ?
C4 C5 C6 C1 -1.3(4) . . . . ?
O4 C5 C6 Cl2 -1.8(5) . . . . ?
C4 C5 C6 Cl2 178.5(2) . . . . ?
Cu1 O5 C7 C12 178.0(2) . . . . ?
Cu1 O5 C7 C8 -4.4(3) . . . . ?
Cu1 O6 C8 C9 -175.1(2) . . . . ?
Cu1 O6 C8 C7 3.9(3) . . . . ?
O5 C7 C8 O6 0.3(4) . . . . ?
C12 C7 C8 O6 178.0(3) . . . . ?
O5 C7 C8 C9 179.4(3) . . . . ?
C12 C7 C8 C9 -2.9(4) . . . . ?
O6 C8 C9 C10 -178.4(3) . . . . ?
C7 C8 C9 C10 2.7(5) . . . . ?
O6 C8 C9 Cl3 2.1(4) . . . . ?
C7 C8 C9 Cl3 -176.8(2) . . . . ?
C8 C9 C10 O7 -178.6(3) . . . . ?
Cl3 C9 C10 O7 0.9(5) . . . . ?
C8 C9 C10 C11 2.0(4) . . . . ?
Cl3 C9 C10 C11 -178.5(2) . . . . ?
O7 C10 C11 O8 -6.3(4) . . . . ?
C9 C10 C11 O8 173.2(3) . . . . ?
O7 C10 C11 C12 173.8(3) . . . . ?
C9 C10 C11 C12 -6.7(4) . . . . ?
O5 C7 C12 C11 175.5(3) . . . . ?
C8 C7 C12 C11 -2.0(4) . . . . ?
O5 C7 C12 Cl4 -1.5(4) . . . . ?
C8 C7 C12 Cl4 -179.0(2) . . . . ?
O8 C11 C12 C7 -173.2(3) . . . . ?
C10 C11 C12 C7 6.7(4) . . . . ?
O8 C11 C12 Cl4 3.8(4) . . . . ?
C10 C11 C12 Cl4 -176.3(2) . . . . ?
Cu1 O9 C13 C14 -76.3(7) . . . . ?
N1 C15 C16 C17 173.3(3) . . . . ?
C15 C16 C17 C18 -177.1(4) . . . . ?
C16 C17 C18 C19 178.5(4) . . . . ?
C17 C18 C19 C20 -179.6(5) . . . . ?
N2 C21 C22 C23 179.7(15) . . . . ?
C21 C22 C23 C24 66(3) . . . . ?
C22 C23 C24 C25 59(3) . . . . ?
C23 C24 C25 C26 149(4) . . . . ?
C27 C28 C29 C30 -88.1(19) . . . . ?
C28 C29 C30 C31 -128(3) . . . . ?
C29 C30 C31 C32 164(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
N2 H2A O5 0.89 1.98 2.864(4) 171.0 .
N2 H2B O3 0.89 2.14 2.975(4) 155.3 1_655
N2 H2B O4 0.89 2.55 3.249(5) 135.4 1_655
N2 H2C O3 0.89 2.38 3.150(4) 144.5 2_665
N2 H2AC O4 0.89 2.14 2.977(4) 156.0 2_665
N2A H2A O5 0.89 1.98 2.864(4) 171.0 .
N2A H2B O3 0.89 2.14 2.975(4) 155.3 1_655
N2A H2C O3 0.89 2.38 3.150(4) 144.5 2_665
N2A H2AC O4 0.89 2.14 2.977(4) 156.0 2_665
O9 H1 O3 0.98(5) 1.80(5) 2.769(4) 173(5) 2_665
N1 H2 O7 0.93(4) 2.00(4) 2.880(4) 157(4) 2_855
N1 H2 O8 0.93(4) 2.32(4) 2.848(4) 116(3) 2_855
N1 H3 O1 0.82(3) 2.05(3) 2.858(4) 173(3) 2_755
N1 H4 Cl4 0.83(4) 2.83(4) 3.522(4) 143(4) .
N1 H4 O8 0.83(4) 2.36(4) 3.073(4) 145(4) .

_refine_diff_density_max         0.553
_refine_diff_density_min         -0.656
_refine_diff_density_rms         0.085

####################################################################### 
# 
# 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_ydkr
_database_code_depnum_ccdc_archive 'CCDC 1521432'
#Added by publCIF



_audit_update_record             
;
2017-01-23 deposited with the CCDC.
2017-02-06 downloaded from the CCDC.
;
_publcif_datablock.id            {6a28ca00-f801-48ef-9623-1831aa88d69a}
# publcif _publ_body_element loop end

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         {(Hha)2[Cu(CA)2(EtOH)]}n
_chemical_formula_sum            'C26 H38 Cl4 Cu N2 O9'
_chemical_formula_weight         727.92

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
Cu Cu 0.3201 1.2651 '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'
C C 0.0033 0.0016 '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'
N N 0.0061 0.0033 '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'

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

_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                   9.9903(3)
_cell_length_b                   12.3925(3)
_cell_length_c                   14.1213(3)
_cell_angle_alpha                68.4083(7)
_cell_angle_beta                 89.2403(9)
_cell_angle_gamma                86.7971(11)
_cell_volume                     1623.02(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    13504
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      27.55

_exptl_crystal_description       block
_exptl_crystal_colour            violet
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.490
_exptl_crystal_F_000             754
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.053
_shelx_estimated_absorpt_T_min   0.678
_shelx_estimated_absorpt_T_max   0.902
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.777
_exptl_absorpt_correction_T_max  0.900
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            16166
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.103
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7412
_reflns_number_gt                6348
_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       'RAPID AUTO (Rigaku, 2011)'
_computing_cell_refinement       'RAPID AUTO (Rigaku, 2011)'
_computing_data_reduction        'RAPID AUTO (Rigaku, 2011)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_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)+(0.0520P)²+0.7346P] 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         7412
_refine_ls_number_parameters     419
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0980
_refine_ls_wR_factor_gt          0.0914
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.088
_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 0.74009(2) 0.23149(2) 0.42182(2) 0.02460(8) Uani 1 1 d . . . . .
Cl1 Cl 0.49506(5) 0.37802(4) 0.66298(4) 0.03141(11) Uani 1 1 d . . . . .
Cl2 Cl 0.29577(5) 0.31958(4) 0.25945(4) 0.03093(11) Uani 1 1 d . . . . .
Cl3 Cl 0.98620(5) 0.06885(5) 0.19436(4) 0.03213(12) Uani 1 1 d . . . . .
Cl4 Cl 1.17995(4) 0.13834(4) 0.59367(3) 0.02437(10) Uani 1 1 d . . . . .
O1 O 0.56286(13) 0.24958(12) 0.36270(10) 0.0264(3) Uani 1 1 d . . . . .
O2 O 0.64838(13) 0.28421(12) 0.52231(10) 0.0282(3) Uani 1 1 d . . . . .
O3 O 0.22289(14) 0.44260(13) 0.56382(12) 0.0345(3) Uani 1 1 d . . . . .
O4 O 0.14472(14) 0.42716(13) 0.39166(12) 0.0370(3) Uani 1 1 d . . . . .
O5 O 0.90899(12) 0.19175(11) 0.49574(10) 0.0251(3) Uani 1 1 d . . . . .
O6 O 0.82681(12) 0.15906(11) 0.33452(10) 0.0246(3) Uani 1 1 d . . . . .
O7 O 1.25966(13) 0.01205(13) 0.29224(11) 0.0300(3) Uani 1 1 d . . . . .
O8 O 1.33331(13) 0.02382(13) 0.47086(10) 0.0292(3) Uani 1 1 d . . . . .
O9 O 0.79240(19) 0.41394(14) 0.32788(12) 0.0412(4) Uani 1 1 d . . . . .
N1 N 1.46733(17) -0.04529(16) 0.67715(13) 0.0269(3) Uani 1 1 d . . . . .
C1 C 0.47669(17) 0.29905(15) 0.40443(13) 0.0213(3) Uani 1 1 d . . . . .
C2 C 0.52668(17) 0.31606(15) 0.49885(13) 0.0223(3) Uani 1 1 d . . . . .
C3 C 0.43964(18) 0.36242(16) 0.55328(13) 0.0230(3) Uani 1 1 d . . . . .
C4 C 0.30781(18) 0.39981(15) 0.51998(15) 0.0247(4) Uani 1 1 d . . . . .
C5 C 0.25947(18) 0.38930(15) 0.42019(14) 0.0244(4) Uani 1 1 d . . . . .
C6 C 0.34945(18) 0.33610(16) 0.36855(14) 0.0227(3) Uani 1 1 d . . . . .
C7 C 0.99861(17) 0.14844(15) 0.45155(13) 0.0199(3) Uani 1 1 d . . . . .
C8 C 0.95040(17) 0.12951(15) 0.35760(13) 0.0210(3) Uani 1 1 d . . . . .
C9 C 1.03931(18) 0.08453(16) 0.30462(13) 0.0230(4) Uani 1 1 d . . . . .
C10 C 1.17447(18) 0.05036(15) 0.33712(13) 0.0224(3) Uani 1 1 d . . . . .
C11 C 1.22007(17) 0.06305(15) 0.43759(13) 0.0214(3) Uani 1 1 d . . . . .
C12 C 1.12810(17) 0.11755(15) 0.48543(13) 0.0214(3) Uani 1 1 d . . . . .
C13 C 0.7911(3) 0.4691(3) 0.2203(2) 0.0602(7) Uani 1 1 d . . . . .
H13A H 0.788237 0.554434 0.201552 0.072 Uiso 1 1 calc R U . . .
H13B H 0.709553 0.449533 0.192330 0.072 Uiso 1 1 calc R U . . .
C14 C 0.9122(4) 0.4318(3) 0.1748(2) 0.0764(10) Uani 1 1 d . . . . .
H14A H 0.910183 0.472892 0.100767 0.115 Uiso 1 1 calc R U . . .
H14B H 0.912979 0.347851 0.190624 0.115 Uiso 1 1 calc R U . . .
H14C H 0.993087 0.450155 0.203138 0.115 Uiso 1 1 calc R U . . .
C15 C 1.4100(2) -0.05554(17) 0.77735(14) 0.0286(4) Uani 1 1 d . . . . .
H15A H 1.459693 -0.119218 0.831801 0.034 Uiso 1 1 calc R U . . .
H15B H 1.315314 -0.075965 0.779599 0.034 Uiso 1 1 calc R U . . .
C16 C 1.4168(2) 0.05585(18) 0.79739(15) 0.0292(4) Uani 1 1 d . . . . .
H16A H 1.375652 0.121310 0.739398 0.035 Uiso 1 1 calc R U . . .
H16B H 1.511739 0.071767 0.803074 0.035 Uiso 1 1 calc R U . . .
C17 C 1.3440(2) 0.0475(2) 0.89483(16) 0.0372(5) Uani 1 1 d . . . . .
H17A H 1.251142 0.025501 0.890460 0.045 Uiso 1 1 calc R U . . .
H17B H 1.389009 -0.015378 0.952741 0.045 Uiso 1 1 calc R U . . .
C18 C 1.3386(3) 0.1589(2) 0.91671(16) 0.0394(5) Uani 1 1 d . . . . .
H18A H 1.431203 0.180020 0.923085 0.047 Uiso 1 1 calc R U . . .
H18B H 1.295121 0.222379 0.858390 0.047 Uiso 1 1 calc R U . . .
C19 C 1.2627(3) 0.1486(2) 1.01294(19) 0.0505(6) Uani 1 1 d . . . . .
H19A H 1.171210 0.124571 1.007242 0.061 Uiso 1 1 calc R U . . .
H19B H 1.307948 0.086490 1.071250 0.061 Uiso 1 1 calc R U . . .
C20 C 1.2515(4) 0.2587(3) 1.0353(2) 0.0625(8) Uani 1 1 d . . . . .
H20A H 1.203505 0.244444 1.099393 0.094 Uiso 1 1 calc R U . . .
H20B H 1.202320 0.319852 0.979858 0.094 Uiso 1 1 calc R U . . .
H20C H 1.341480 0.283488 1.041211 0.094 Uiso 1 1 calc R U . . .
N2 N 0.95531(18) 0.35494(15) 0.58909(14) 0.0350(4) Uani 0.6 1 d . . P . .
H2A H 0.891656 0.414505 0.568883 0.053 Uiso 0.6 1 calc R U P . .
H2B H 0.932479 0.298289 0.566693 0.053 Uiso 0.6 1 calc R U P . .
H2C H 1.035869 0.381578 0.562501 0.053 Uiso 0.6 1 calc R U P . .
C21 C 0.9652(4) 0.3058(3) 0.7042(3) 0.0371(7) Uani 0.6 1 d D . P . .
H21A H 1.044813 0.251094 0.726342 0.045 Uiso 0.6 1 calc R U P . .
H21B H 0.974805 0.369351 0.729807 0.045 Uiso 0.6 1 calc R U P . .
C22 C 0.8410(5) 0.2438(4) 0.7461(3) 0.0556(9) Uani 0.6 1 d D . P . .
H22A H 0.832848 0.181122 0.719236 0.067 Uiso 0.6 1 calc R U P . .
H22B H 0.762432 0.299246 0.721200 0.067 Uiso 0.6 1 calc R U P . .
C23 C 0.8366(11) 0.1909(6) 0.8623(5) 0.092(2) Uani 0.6 1 d D . P . .
H23A H 0.761702 0.138111 0.880556 0.110 Uiso 0.6 1 calc R U P . .
H23B H 0.920125 0.141586 0.885373 0.110 Uiso 0.6 1 calc R U P . .
C24 C 0.8225(10) 0.2611(7) 0.9213(5) 0.108(2) Uani 0.6 1 d D . P . .
H24A H 0.908278 0.299091 0.916149 0.129 Uiso 0.6 1 calc R U P . .
H24B H 0.815024 0.207545 0.992995 0.129 Uiso 0.6 1 calc R U P . .
C25 C 0.7151(13) 0.3526(8) 0.9042(7) 0.143(4) Uani 0.6 1 d D . P . .
H25A H 0.635485 0.324843 0.880947 0.172 Uiso 0.6 1 calc R U P . .
H25B H 0.743422 0.420751 0.845799 0.172 Uiso 0.6 1 calc R U P . .
C26 C 0.6658(13) 0.3991(10) 0.9871(9) 0.123(3) Uani 0.6 1 d D . P . .
H26A H 0.735752 0.443428 1.001420 0.185 Uiso 0.6 1 calc R U P . .
H26B H 0.645801 0.333591 1.049380 0.185 Uiso 0.6 1 calc R U P . .
H26C H 0.584549 0.449599 0.962947 0.185 Uiso 0.6 1 calc R U P . .
N2A N 0.95531(18) 0.35494(15) 0.58909(14) 0.0350(4) Uani 0.4 1 d . . P A 1
H2AA H 0.981655 0.419976 0.597512 0.053 Uiso 0.4 1 calc R U P A 1
H2AB H 0.891556 0.375116 0.539252 0.053 Uiso 0.4 1 calc R U P A 1
H2AC H 1.027120 0.318352 0.571119 0.053 Uiso 0.4 1 calc R U P A 1
C27 C 0.8972(6) 0.2728(5) 0.6894(4) 0.0371(7) Uani 0.4 1 d D . P A 1
H27A H 0.798938 0.287889 0.690447 0.045 Uiso 0.4 1 calc R U P A 1
H27B H 0.915426 0.190906 0.696186 0.045 Uiso 0.4 1 calc R U P A 1
C28 C 0.9617(8) 0.2941(7) 0.7746(5) 0.0556(9) Uani 0.4 1 d D . P A 1
H28A H 0.955983 0.378261 0.761827 0.067 Uiso 0.4 1 calc R U P A 1
H28B H 1.057593 0.267396 0.779914 0.067 Uiso 0.4 1 calc R U P A 1
C29 C 0.8885(15) 0.2263(9) 0.8757(9) 0.092(2) Uani 0.4 1 d D . P A 1
H29A H 0.949926 0.206220 0.934876 0.110 Uiso 0.4 1 calc R U P A 1
H29B H 0.853727 0.153960 0.873629 0.110 Uiso 0.4 1 calc R U P A 1
C30 C 0.7667(15) 0.3153(12) 0.8823(7) 0.108(2) Uani 0.4 1 d D . P A 1
H30A H 0.797176 0.395461 0.852118 0.129 Uiso 0.4 1 calc R U P A 1
H30B H 0.691306 0.309592 0.839848 0.129 Uiso 0.4 1 calc R U P A 1
C31 C 0.7195(18) 0.2978(12) 0.9783(9) 0.143(4) Uani 0.4 1 d D . P A 1
H31A H 0.788993 0.307456 1.023477 0.172 Uiso 0.4 1 calc R U P A 1
H31B H 0.680565 0.221103 1.010630 0.172 Uiso 0.4 1 calc R U P A 1
C32 C 0.619(2) 0.3922(16) 0.9486(15) 0.123(3) Uani 0.4 1 d D . P A 1
H32A H 0.659378 0.464145 0.943854 0.185 Uiso 0.4 1 calc R U P A 1
H32B H 0.547406 0.375175 0.999477 0.185 Uiso 0.4 1 calc R U P A 1
H32C H 0.580856 0.401453 0.882198 0.185 Uiso 0.4 1 calc R U P A 1
H1 H 0.776(3) 0.453(2) 0.351(2) 0.038(8) Uiso 1 1 d . . . . .
H2 H 1.547(3) -0.024(2) 0.6736(18) 0.035(6) Uiso 1 1 d . . . . .
H3 H 1.465(3) -0.110(2) 0.6647(19) 0.040(7) Uiso 1 1 d . . . . .
H4 H 1.412(3) 0.000(2) 0.6289(18) 0.034(6) 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 O1 1.9338(13) . ?
Cu1 O5 1.9377(13) . ?
Cu1 O6 1.9430(12) . ?
Cu1 O2 1.9649(13) . ?
Cu1 O9 2.2475(17) . ?
Cl1 C3 1.7317(18) . ?
Cl2 C6 1.7231(18) . ?
Cl3 C9 1.7319(18) . ?
Cl4 C12 1.7311(18) . ?
O1 C1 1.288(2) . ?
O2 C2 1.267(2) . ?
O3 C4 1.250(2) . ?
O4 C5 1.229(2) . ?
O5 C7 1.287(2) . ?
O6 C8 1.279(2) . ?
O7 C10 1.230(2) . ?
O8 C11 1.233(2) . ?
O9 C13 1.418(3) . ?
O9 H1 0.69(3) . ?
N1 C15 1.483(2) . ?
N1 H2 0.85(3) . ?
N1 H3 0.88(3) . ?
N1 H4 0.88(3) . ?
C1 C6 1.365(3) . ?
C1 C2 1.519(2) . ?
C2 C3 1.389(2) . ?
C3 C4 1.399(3) . ?
C4 C5 1.548(3) . ?
C5 C6 1.430(2) . ?
C7 C12 1.369(2) . ?
C7 C8 1.518(2) . ?
C8 C9 1.376(2) . ?
C9 C10 1.422(2) . ?
C10 C11 1.560(2) . ?
C11 C12 1.417(2) . ?
C13 C14 1.492(4) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.513(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.520(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.519(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.515(3) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.508(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
N2 C21 1.514(4) . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N2 H2C 0.9100 . ?
C21 C22 1.494(6) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.527(8) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C23 C24 1.409(9) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.472(10) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.547(11) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 C28 1.484(8) . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
C28 C29 1.561(11) . ?
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
C29 C30 1.621(14) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C30 C31 1.374(13) . ?
C30 H30A 0.9900 . ?
C30 H30B 0.9900 . ?
C31 C32 1.442(15) . ?
C31 H31A 0.9900 . ?
C31 H31B 0.9900 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 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
O1 Cu1 O5 171.45(6) . . ?
O1 Cu1 O6 96.31(5) . . ?
O5 Cu1 O6 84.33(5) . . ?
O1 Cu1 O2 83.94(5) . . ?
O5 Cu1 O2 94.33(5) . . ?
O6 Cu1 O2 172.58(6) . . ?
O1 Cu1 O9 94.05(6) . . ?
O5 Cu1 O9 94.36(6) . . ?
O6 Cu1 O9 96.17(6) . . ?
O2 Cu1 O9 91.21(6) . . ?
C1 O1 Cu1 112.53(11) . . ?
C2 O2 Cu1 112.31(11) . . ?
C7 O5 Cu1 112.49(11) . . ?
C8 O6 Cu1 112.69(11) . . ?
C13 O9 Cu1 128.06(17) . . ?
C13 O9 H1 111(2) . . ?
Cu1 O9 H1 113(2) . . ?
C15 N1 H2 109.4(16) . . ?
C15 N1 H3 113.3(16) . . ?
H2 N1 H3 110(2) . . ?
C15 N1 H4 108.5(15) . . ?
H2 N1 H4 115(2) . . ?
H3 N1 H4 100(2) . . ?
O1 C1 C6 124.38(16) . . ?
O1 C1 C2 115.02(15) . . ?
C6 C1 C2 120.60(15) . . ?
O2 C2 C3 124.81(17) . . ?
O2 C2 C1 115.38(15) . . ?
C3 C2 C1 119.81(16) . . ?
C2 C3 C4 121.28(16) . . ?
C2 C3 Cl1 119.90(14) . . ?
C4 C3 Cl1 118.81(13) . . ?
O3 C4 C3 125.65(18) . . ?
O3 C4 C5 115.50(17) . . ?
C3 C4 C5 118.85(15) . . ?
O4 C5 C6 124.78(18) . . ?
O4 C5 C4 116.74(16) . . ?
C6 C5 C4 118.48(15) . . ?
C1 C6 C5 120.81(16) . . ?
C1 C6 Cl2 120.01(13) . . ?
C5 C6 Cl2 119.18(14) . . ?
O5 C7 C12 124.39(16) . . ?
O5 C7 C8 115.11(15) . . ?
C12 C7 C8 120.48(15) . . ?
O6 C8 C9 125.64(16) . . ?
O6 C8 C7 114.98(15) . . ?
C9 C8 C7 119.37(15) . . ?
C8 C9 C10 122.22(16) . . ?
C8 C9 Cl3 119.37(14) . . ?
C10 C9 Cl3 118.42(13) . . ?
O7 C10 C9 125.49(17) . . ?
O7 C10 C11 116.72(16) . . ?
C9 C10 C11 117.79(15) . . ?
O8 C11 C12 124.21(16) . . ?
O8 C11 C10 117.90(15) . . ?
C12 C11 C10 117.88(15) . . ?
C7 C12 C11 121.93(16) . . ?
C7 C12 Cl4 119.57(13) . . ?
C11 C12 Cl4 118.41(13) . . ?
O9 C13 C14 111.2(3) . . ?
O9 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
O9 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 C16 112.16(16) . . ?
N1 C15 H15A 109.2 . . ?
C16 C15 H15A 109.2 . . ?
N1 C15 H15B 109.2 . . ?
C16 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C15 C16 C17 111.09(17) . . ?
C15 C16 H16A 109.4 . . ?
C17 C16 H16A 109.4 . . ?
C15 C16 H16B 109.4 . . ?
C17 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
C18 C17 C16 114.26(18) . . ?
C18 C17 H17A 108.7 . . ?
C16 C17 H17A 108.7 . . ?
C18 C17 H17B 108.7 . . ?
C16 C17 H17B 108.7 . . ?
H17A C17 H17B 107.6 . . ?
C19 C18 C17 113.00(19) . . ?
C19 C18 H18A 109.0 . . ?
C17 C18 H18A 109.0 . . ?
C19 C18 H18B 109.0 . . ?
C17 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C20 C19 C18 114.5(2) . . ?
C20 C19 H19A 108.6 . . ?
C18 C19 H19A 108.6 . . ?
C20 C19 H19B 108.6 . . ?
C18 C19 H19B 108.6 . . ?
H19A C19 H19B 107.6 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C21 N2 H2A 109.5 . . ?
C21 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C21 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C22 C21 N2 108.8(3) . . ?
C22 C21 H21A 109.9 . . ?
N2 C21 H21A 109.9 . . ?
C22 C21 H21B 109.9 . . ?
N2 C21 H21B 109.9 . . ?
H21A C21 H21B 108.3 . . ?
C21 C22 C23 114.4(5) . . ?
C21 C22 H22A 108.7 . . ?
C23 C22 H22A 108.7 . . ?
C21 C22 H22B 108.7 . . ?
C23 C22 H22B 108.7 . . ?
H22A C22 H22B 107.6 . . ?
C24 C23 C22 121.5(6) . . ?
C24 C23 H23A 106.9 . . ?
C22 C23 H23A 106.9 . . ?
C24 C23 H23B 106.9 . . ?
C22 C23 H23B 106.9 . . ?
H23A C23 H23B 106.7 . . ?
C23 C24 C25 123.2(9) . . ?
C23 C24 H24A 106.5 . . ?
C25 C24 H24A 106.5 . . ?
C23 C24 H24B 106.5 . . ?
C25 C24 H24B 106.5 . . ?
H24A C24 H24B 106.5 . . ?
C24 C25 C26 123.5(9) . . ?
C24 C25 H25A 106.5 . . ?
C26 C25 H25A 106.5 . . ?
C24 C25 H25B 106.5 . . ?
C26 C25 H25B 106.5 . . ?
H25A C25 H25B 106.5 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C28 C27 H27A 110.1 . . ?
C28 C27 H27B 110.1 . . ?
H27A C27 H27B 108.4 . . ?
C27 C28 C29 108.9(7) . . ?
C27 C28 H28A 109.9 . . ?
C29 C28 H28A 109.9 . . ?
C27 C28 H28B 109.9 . . ?
C29 C28 H28B 109.9 . . ?
H28A C28 H28B 108.3 . . ?
C28 C29 C30 104.6(8) . . ?
C28 C29 H29A 110.8 . . ?
C30 C29 H29A 110.8 . . ?
C28 C29 H29B 110.8 . . ?
C30 C29 H29B 110.8 . . ?
H29A C29 H29B 108.9 . . ?
C31 C30 C29 115.7(10) . . ?
C31 C30 H30A 108.4 . . ?
C29 C30 H30A 108.4 . . ?
C31 C30 H30B 108.4 . . ?
C29 C30 H30B 108.4 . . ?
H30A C30 H30B 107.4 . . ?
C30 C31 C32 96.8(13) . . ?
C30 C31 H31A 112.4 . . ?
C32 C31 H31A 112.4 . . ?
C30 C31 H31B 112.4 . . ?
C32 C31 H31B 112.4 . . ?
H31A C31 H31B 110.0 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cu1 O1 C1 C6 170.87(15) . . . . ?
Cu1 O1 C1 C2 -8.38(19) . . . . ?
Cu1 O2 C2 C3 -176.80(14) . . . . ?
Cu1 O2 C2 C1 4.02(19) . . . . ?
O1 C1 C2 O2 2.9(2) . . . . ?
C6 C1 C2 O2 -176.34(17) . . . . ?
O1 C1 C2 C3 -176.29(16) . . . . ?
C6 C1 C2 C3 4.4(3) . . . . ?
O2 C2 C3 C4 177.43(17) . . . . ?
C1 C2 C3 C4 -3.4(3) . . . . ?
O2 C2 C3 Cl1 -1.0(3) . . . . ?
C1 C2 C3 Cl1 178.15(13) . . . . ?
C2 C3 C4 O3 -179.90(18) . . . . ?
Cl1 C3 C4 O3 -1.5(3) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
Cl1 C3 C4 C5 178.19(13) . . . . ?
O3 C4 C5 O4 2.4(3) . . . . ?
C3 C4 C5 O4 -177.33(18) . . . . ?
O3 C4 C5 C6 -177.12(17) . . . . ?
C3 C4 C5 C6 3.2(3) . . . . ?
O1 C1 C6 C5 179.37(17) . . . . ?
C2 C1 C6 C5 -1.4(3) . . . . ?
O1 C1 C6 Cl2 -0.9(3) . . . . ?
C2 C1 C6 Cl2 178.29(13) . . . . ?
O4 C5 C6 C1 178.33(19) . . . . ?
C4 C5 C6 C1 -2.2(3) . . . . ?
O4 C5 C6 Cl2 -1.4(3) . . . . ?
C4 C5 C6 Cl2 178.04(13) . . . . ?
Cu1 O5 C7 C12 177.16(14) . . . . ?
Cu1 O5 C7 C8 -4.49(18) . . . . ?
Cu1 O6 C8 C9 -174.88(15) . . . . ?
Cu1 O6 C8 C7 4.52(18) . . . . ?
O5 C7 C8 O6 0.0(2) . . . . ?
C12 C7 C8 O6 178.40(16) . . . . ?
O5 C7 C8 C9 179.42(16) . . . . ?
C12 C7 C8 C9 -2.2(3) . . . . ?
O6 C8 C9 C10 -177.99(17) . . . . ?
C7 C8 C9 C10 2.6(3) . . . . ?
O6 C8 C9 Cl3 2.2(3) . . . . ?
C7 C8 C9 Cl3 -177.21(13) . . . . ?
C8 C9 C10 O7 -178.30(18) . . . . ?
Cl3 C9 C10 O7 1.5(3) . . . . ?
C8 C9 C10 C11 1.2(3) . . . . ?
Cl3 C9 C10 C11 -178.98(12) . . . . ?
O7 C10 C11 O8 -6.9(3) . . . . ?
C9 C10 C11 O8 173.55(17) . . . . ?
O7 C10 C11 C12 173.88(16) . . . . ?
C9 C10 C11 C12 -5.6(2) . . . . ?
O5 C7 C12 C11 175.69(17) . . . . ?
C8 C7 C12 C11 -2.6(3) . . . . ?
O5 C7 C12 Cl4 -0.9(3) . . . . ?
C8 C7 C12 Cl4 -179.18(13) . . . . ?
O8 C11 C12 C7 -172.83(17) . . . . ?
C10 C11 C12 C7 6.3(3) . . . . ?
O8 C11 C12 Cl4 3.8(3) . . . . ?
C10 C11 C12 Cl4 -177.04(12) . . . . ?
Cu1 O9 C13 C14 -78.2(3) . . . . ?
N1 C15 C16 C17 173.77(17) . . . . ?
C15 C16 C17 C18 -176.27(19) . . . . ?
C16 C17 C18 C19 178.7(2) . . . . ?
C17 C18 C19 C20 -178.2(2) . . . . ?
N2 C21 C22 C23 -179.2(4) . . . . ?
C21 C22 C23 C24 69.6(11) . . . . ?
C22 C23 C24 C25 52.3(14) . . . . ?
C23 C24 C25 C26 157.1(11) . . . . ?
C27 C28 C29 C30 -88.0(10) . . . . ?
C28 C29 C30 C31 -155.8(14) . . . . ?
C29 C30 C31 C32 179.5(14) . . . . ?

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
C16 H16A Cl4 0.99 2.80 3.559(2) 133.8 .
N2 H2A O3 0.91 2.31 3.121(2) 148.0 2_666
N2 H2AC Cl4 0.91 2.55 3.3836(17) 152.0 .
N2 H2B O5 0.91 1.95 2.850(2) 168.1 .
N2 H2C O3 0.91 2.06 2.910(2) 155.5 1_655
C22 H22B Cl1 0.99 2.82 3.757(5) 158.6 .
N2A H2A O3 0.91 2.31 3.121(2) 148.0 2_666
N2A H2A O4 0.91 2.24 2.932(2) 132.6 2_666
N2A H2AC Cl4 0.91 2.55 3.3836(17) 152.0 .
N2A H2B O5 0.91 1.95 2.850(2) 168.1 .
N2A H2C O3 0.91 2.06 2.910(2) 155.5 1_655
O9 H1 O3 0.69(3) 2.07(3) 2.736(2) 164(3) 2_666
N1 H2 O7 0.85(3) 2.02(3) 2.843(2) 162(2) 2_856
N1 H2 O8 0.85(3) 2.35(2) 2.819(2) 115.1(19) 2_856
N1 H3 O1 0.88(3) 1.94(3) 2.820(2) 173(2) 2_756
N1 H4 Cl4 0.88(3) 2.74(3) 3.4923(18) 143.6(19) .
N1 H4 O8 0.88(3) 2.29(2) 3.025(2) 141(2) .

_refine_diff_density_max         0.590
_refine_diff_density_min         -0.578
_refine_diff_density_rms         0.081


loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max

loop_
_publcif_info_exptl_table_header_item
?
