# 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_compound_2
_database_code_depnum_ccdc_archive 'CCDC 1520628'
_audit_update_record             
;
2016-12-04 deposited with the CCDC.
2017-01-30 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-2013
_chemical_name_systematic        'Compound 2'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H19 Cl3 Cu2 N6 O4, C H4 O'
_chemical_formula_sum            'C16 H23 Cl3 Cu2 N6 O5'
_chemical_formula_weight         612.83

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

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   11.0539(9)
_cell_length_b                   16.0359(14)
_cell_length_c                   13.2399(11)
_cell_angle_alpha                90
_cell_angle_beta                 103.545(2)
_cell_angle_gamma                90
_cell_volume                     2281.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9868
_cell_measurement_theta_min      2.51
_cell_measurement_theta_max      28.97

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.784
_exptl_crystal_F_000             1240
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.257
_shelx_estimated_absorpt_T_min   0.649
_shelx_estimated_absorpt_T_max   0.806
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6486
_exptl_absorpt_correction_T_max  0.8058
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
Sadabs 2012/1, Bruker AXS, wisconsin, USA 
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22508
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.511
_diffrn_reflns_theta_max         29.055
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             5944
_reflns_number_gt                5158
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_refine_special_details          
;
 Structure solved by direct methods to reveal non-H atoms. Remaining non-H
 atoms located in subsequent difference maps. All non-H refined anisotropically.
 H atoms added at calculated positions for C-H and N-H groups and refined
 with a riding model. O-H H atoms were located in difference map and refined
 with U(iso) riding on the O and DFIX constraints applied. 

;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0135P)²+3.7137P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5944
_refine_ls_number_parameters     309
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0715
_refine_ls_wR_factor_gt          0.0687
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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 0.58752(2) 0.11777(2) 0.87303(2) 0.01203(7) Uani 1 1 d . . . . .
Cl1 Cl 1.05669(5) 0.15904(4) 0.66003(5) 0.02342(13) Uani 1 1 d . . . . .
O1 O 0.60110(15) -0.05157(11) 0.68440(12) 0.0189(3) Uani 1 1 d . . . . .
N1 N 0.45717(17) 0.16421(12) 0.94376(14) 0.0148(4) Uani 1 1 d . . . . .
Cu2 Cu 0.88921(2) 0.11202(2) 0.72047(2) 0.01328(7) Uani 1 1 d . . . . .
Cl2 Cl 0.50633(5) 0.15924(4) 0.71203(4) 0.01852(12) Uani 1 1 d . . . . .
N2 N 0.64109(16) 0.06646(11) 1.00920(13) 0.0120(3) Uani 1 1 d . . . . .
O2 O 0.88286(16) 0.04931(12) 0.50305(12) 0.0223(4) Uani 1 1 d D . . . .
H2 H 0.947(2) 0.0799(17) 0.528(2) 0.027 Uiso 1 1 d D U . . .
Cl3 Cl 0.95694(5) 0.16818(3) 0.88166(4) 0.01643(11) Uani 1 1 d . . . . .
N3 N 0.88065(16) -0.04822(12) 0.92925(14) 0.0141(4) Uani 1 1 d . . . . .
H3A H 0.9055 -0.0563 0.8715 0.017 Uiso 1 1 calc R U . . .
H3B H 0.9191 -0.0734 0.9869 0.017 Uiso 1 1 calc R U . . .
N4 N 0.72079(16) 0.04281(11) 0.84872(13) 0.0119(3) Uani 1 1 d . . . . .
N5 N 0.76445(16) 0.03696(11) 0.75751(13) 0.0117(3) Uani 1 1 d . . . . .
N6 N 0.83351(17) 0.04414(12) 0.59050(14) 0.0157(4) Uani 1 1 d . . . . .
C11 C 0.3611(2) 0.21363(15) 0.90137(19) 0.0191(5) Uani 1 1 d . . . . .
H11 H 0.3518 0.2317 0.8316 0.023 Uiso 1 1 calc R U . . .
C12 C 0.2745(2) 0.23934(15) 0.9557(2) 0.0216(5) Uani 1 1 d . . . . .
H12 H 0.2067 0.2740 0.9233 0.026 Uiso 1 1 calc R U . . .
C13 C 0.2879(2) 0.21409(15) 1.0571(2) 0.0208(5) Uani 1 1 d . . . . .
H13 H 0.2303 0.2319 1.0959 0.025 Uiso 1 1 calc R U . . .
C14 C 0.3870(2) 0.16205(14) 1.10227(18) 0.0175(5) Uani 1 1 d . . . . .
H14 H 0.3975 0.1433 1.1718 0.021 Uiso 1 1 calc R U . . .
C15 C 0.4697(2) 0.13834(14) 1.04361(17) 0.0136(4) Uani 1 1 d . . . . .
C16 C 0.57635(19) 0.08120(13) 1.08113(16) 0.0127(4) Uani 1 1 d . . . . .
C17 C 0.6093(2) 0.04151(14) 1.17779(17) 0.0159(4) Uani 1 1 d . . . . .
H17 H 0.5629 0.0503 1.2289 0.019 Uiso 1 1 calc R U . . .
C18 C 0.7119(2) -0.01106(15) 1.19679(17) 0.0167(4) Uani 1 1 d . . . . .
H18 H 0.7374 -0.0375 1.2625 0.020 Uiso 1 1 calc R U . . .
C19 C 0.7784(2) -0.02571(14) 1.12064(16) 0.0150(4) Uani 1 1 d . . . . .
H19 H 0.8487 -0.0616 1.1336 0.018 Uiso 1 1 calc R U . . .
C20 C 0.73818(19) 0.01402(13) 1.02566(16) 0.0109(4) Uani 1 1 d . . . . .
C21 C 0.78496(19) 0.00209(13) 0.92934(15) 0.0108(4) Uani 1 1 d . . . . .
C22 C 0.6923(2) -0.00808(14) 0.68084(16) 0.0133(4) Uani 1 1 d . . . . .
C23 C 0.7380(2) -0.00300(14) 0.58195(16) 0.0141(4) Uani 1 1 d . . . . .
C24 C 0.6743(2) -0.04901(16) 0.48724(17) 0.0215(5) Uani 1 1 d . . . . .
H24A H 0.6229 -0.0103 0.4380 0.032 Uiso 1 1 calc R U . . .
H24B H 0.6214 -0.0926 0.5060 0.032 Uiso 1 1 calc R U . . .
H24C H 0.7366 -0.0746 0.4551 0.032 Uiso 1 1 calc R U . . .
O31 O 0.71339(15) 0.23795(11) 0.93567(13) 0.0192(3) Uani 1 1 d D . . . .
H31 H 0.777(2) 0.2249(19) 0.917(2) 0.029 Uiso 1 1 d D U . . .
C31 C 0.6651(3) 0.31332(16) 0.8824(2) 0.0292(6) Uani 1 1 d . . . . .
H31A H 0.6494 0.3045 0.8072 0.044 Uiso 1 1 calc R U . . .
H31B H 0.7257 0.3584 0.9028 0.044 Uiso 1 1 calc R U . . .
H31C H 0.5871 0.3285 0.9009 0.044 Uiso 1 1 calc R U . . .
O51 O 0.75741(17) 0.22102(12) 0.65399(14) 0.0226(4) Uani 1 1 d D . . . .
H1W H 0.751(3) 0.2331(19) 0.5903(15) 0.034(9) Uiso 1 1 d D . . . .
H2W H 0.685(2) 0.209(2) 0.663(3) 0.047(10) Uiso 1 1 d D . . . .
O1S O 0.9381(2) -0.14490(13) 0.75933(17) 0.0405(5) Uani 1 1 d D . . . .
H1S H 0.951(4) -0.1955(14) 0.780(3) 0.061 Uiso 1 1 d D U . . .
C1S C 1.0261(3) -0.12190(18) 0.7018(2) 0.0311(6) Uani 1 1 d . . . . .
H1S1 H 1.0289 -0.0610 0.6966 0.047 Uiso 1 1 calc R U . . .
H1S2 H 1.0018 -0.1460 0.6320 0.047 Uiso 1 1 calc R U . . .
H1S3 H 1.1085 -0.1428 0.7371 0.047 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N2 1.9437(18) . ?
Cu1 N4 1.9852(18) . ?
Cu1 N1 2.0346(19) . ?
Cu1 Cl2 2.2125(6) . ?
Cu1 O31 2.4077(17) . ?
Cl1 Cu2 2.3087(6) . ?
O1 C22 1.236(3) . ?
N1 C11 1.339(3) . ?
N1 C15 1.361(3) . ?
Cu2 N5 1.9769(18) . ?
Cu2 N6 2.0072(19) . ?
Cu2 Cl3 2.2754(6) . ?
Cu2 O51 2.3134(18) . ?
N2 C16 1.339(3) . ?
N2 C20 1.340(3) . ?
O2 N6 1.393(2) . ?
O2 H2 0.858(17) . ?
N3 C21 1.330(3) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N4 C21 1.309(3) . ?
N4 N5 1.405(2) . ?
N5 C22 1.345(3) . ?
N6 C23 1.282(3) . ?
C11 C12 1.388(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.377(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.395(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.385(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.484(3) . ?
C16 C17 1.399(3) . ?
C17 C18 1.388(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.400(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.387(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.496(3) . ?
C22 C23 1.512(3) . ?
C23 C24 1.483(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
O31 C31 1.438(3) . ?
O31 H31 0.823(17) . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
O51 H1W 0.851(17) . ?
O51 H2W 0.863(18) . ?
O1S C1S 1.418(3) . ?
O1S H1S 0.858(18) . ?
C1S H1S1 0.9800 . ?
C1S H1S2 0.9800 . ?
C1S H1S3 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 N4 79.49(7) . . ?
N2 Cu1 N1 79.79(8) . . ?
N4 Cu1 N1 158.23(7) . . ?
N2 Cu1 Cl2 170.96(6) . . ?
N4 Cu1 Cl2 100.06(5) . . ?
N1 Cu1 Cl2 99.34(6) . . ?
N2 Cu1 O31 89.62(7) . . ?
N4 Cu1 O31 98.61(7) . . ?
N1 Cu1 O31 87.87(7) . . ?
Cl2 Cu1 O31 99.36(4) . . ?
C11 N1 C15 118.55(19) . . ?
C11 N1 Cu1 126.99(16) . . ?
C15 N1 Cu1 114.41(15) . . ?
N5 Cu2 N6 77.92(7) . . ?
N5 Cu2 Cl3 95.95(5) . . ?
N6 Cu2 Cl3 170.47(6) . . ?
N5 Cu2 Cl1 161.35(6) . . ?
N6 Cu2 Cl1 89.42(6) . . ?
Cl3 Cu2 Cl1 94.67(2) . . ?
N5 Cu2 O51 98.09(7) . . ?
N6 Cu2 O51 92.53(7) . . ?
Cl3 Cu2 O51 95.59(5) . . ?
Cl1 Cu2 O51 96.09(5) . . ?
C16 N2 C20 122.40(18) . . ?
C16 N2 Cu1 119.17(15) . . ?
C20 N2 Cu1 118.34(14) . . ?
N6 O2 H2 99(2) . . ?
C21 N3 H3A 120.0 . . ?
C21 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C21 N4 N5 115.98(17) . . ?
C21 N4 Cu1 116.79(14) . . ?
N5 N4 Cu1 126.67(13) . . ?
C22 N5 N4 114.99(17) . . ?
C22 N5 Cu2 117.67(14) . . ?
N4 N5 Cu2 124.94(13) . . ?
C23 N6 O2 115.89(18) . . ?
C23 N6 Cu2 118.45(15) . . ?
O2 N6 Cu2 125.38(14) . . ?
N1 C11 C12 122.3(2) . . ?
N1 C11 H11 118.8 . . ?
C12 C11 H11 118.8 . . ?
C13 C12 C11 119.2(2) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C12 C13 C14 119.2(2) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C15 C14 C13 118.6(2) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
N1 C15 C14 122.0(2) . . ?
N1 C15 C16 113.94(18) . . ?
C14 C15 C16 124.0(2) . . ?
N2 C16 C17 120.1(2) . . ?
N2 C16 C15 112.69(18) . . ?
C17 C16 C15 127.13(19) . . ?
C18 C17 C16 118.0(2) . . ?
C18 C17 H17 121.0 . . ?
C16 C17 H17 121.0 . . ?
C17 C18 C19 121.1(2) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C20 C19 C18 117.7(2) . . ?
C20 C19 H19 121.1 . . ?
C18 C19 H19 121.1 . . ?
N2 C20 C19 120.67(19) . . ?
N2 C20 C21 111.41(17) . . ?
C19 C20 C21 127.78(19) . . ?
N4 C21 N3 125.50(19) . . ?
N4 C21 C20 113.68(18) . . ?
N3 C21 C20 120.78(18) . . ?
O1 C22 N5 128.2(2) . . ?
O1 C22 C23 120.29(19) . . ?
N5 C22 C23 111.45(18) . . ?
N6 C23 C24 125.9(2) . . ?
N6 C23 C22 112.99(19) . . ?
C24 C23 C22 121.13(19) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C31 O31 Cu1 112.67(14) . . ?
C31 O31 H31 108(2) . . ?
Cu1 O31 H31 99(2) . . ?
O31 C31 H31A 109.5 . . ?
O31 C31 H31B 109.5 . . ?
H31A C31 H31B 109.5 . . ?
O31 C31 H31C 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
Cu2 O51 H1W 117(2) . . ?
Cu2 O51 H2W 107(2) . . ?
H1W O51 H2W 109(3) . . ?
C1S O1S H1S 109(3) . . ?
O1S C1S H1S1 109.5 . . ?
O1S C1S H1S2 109.5 . . ?
H1S1 C1S H1S2 109.5 . . ?
O1S C1S H1S3 109.5 . . ?
H1S1 C1S H1S3 109.5 . . ?
H1S2 C1S H1S3 109.5 . . ?

_refine_diff_density_max         0.543
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.086

_shelxl_version_number           2013-3

####################################################################### 
# 
# 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_compound_4
_database_code_depnum_ccdc_archive 'CCDC 1520630'
_audit_update_record             
;
2016-12-04 deposited with the CCDC.
2017-01-30 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT018_compound_4          
;
PROBLEM: _diffrn_measured_fraction_theta_max .NE. *_full           ! Check
RESPONSE: This was a weakly diffracting crystal. 99.6% of data were measured
to 55 deg/2theta.
;
_vrf_PLAT213_compound_4          
;
PROBLEM: Atom O11             has ADP max/min Ratio .....        3.6 prolat
RESPONSE: The NO3 anion showed significant libration which was more exacerbated
for O13 than O11 and O12 which are involved in H-bonding. The NO3- was modelled
as a rocking disorder over two sites with O11 and O12 common to both sites. The
slightly prolate U(ij) for O11 likely arises from unresolved disorder in this anion.  
 
;
_vrf_PLAT220_compound_4          
;
PROBLEM: Non-Solvent Resd 1   O   Ueq(max)/Ueq(min) Range        4.3 Ratio 
RESPONSE: ...
;
_vrf_PLAT241_compound_4          
;
PROBLEM: High   'MainMol' Ueq as Compared to Neighbors of        O11 Check 
RESPONSE: ...
;
_vrf_PLAT242_compound_4          
;
PROBLEM: Low    'MainMol' Ueq as Compared to Neighbors of        Cu1 Check 
RESPONSE: This is a reflection of disorder in the coordination environment about
Cu1 which has disordered MeOH/EtOH coordinated solvent located around a 2-fold axis. 
;
_vrf_PLAT341_compound_4          
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.00967 Ang.  
RESPONSE: ...
;
_vrf_PLAT906_compound_4          
;
PROBLEM: Large K value in the Analysis of Variance ......      4.829 Check 
RESPONSE: ...
;
_vrf_PLAT911_compound_4          
;
PROBLEM: Missing # FCF Refl Between THmin & STh/L=  0.539          8 Report
RESPONSE: ...
;
_vrf_PLAT977_compound_4          
;
PROBLEM: Check the Negative Difference Density on     H1S      -0.31 eA-3  
RESPONSE: This residual negative electron density is in the vicinity of the 
disordered MeOH/EtOH coordinated solvent which is located adjacent to a 2-fold axis
and is an artifact of the imperfect mdelling of the solvent disorder.
;
# end Validation Reply Form
_audit_creation_method           SHELXL-2013
_chemical_name_systematic        'Compound 4'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29.50, H29 Cu3 N12 O5, 2 (N O3)'
_chemical_formula_sum            'C29.50 H29 Cu3 N14 O11'
_chemical_formula_weight         946.29

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

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   24.005(17)
_cell_length_b                   7.518(5)
_cell_length_c                   21.135(15)
_cell_angle_alpha                90
_cell_angle_beta                 116.849(17)
_cell_angle_gamma                90
_cell_volume                     3403(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2472
_cell_measurement_theta_min      2.87
_cell_measurement_theta_max      22.46

_exptl_crystal_description       plate
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.847
_exptl_crystal_F_000             1916
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    1.943
_shelx_estimated_absorpt_T_min   0.845
_shelx_estimated_absorpt_T_max   0.909
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8445
_exptl_absorpt_correction_T_max  0.9091
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
Crystal weakly diffracting to high angle.
Sadabs 2012/1, Bruker AXS, wisconsin, USA 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12480
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_av_R_equivalents  0.0683
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.902
_diffrn_reflns_theta_max         22.546
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.726
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.726
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.726
_reflns_number_total             2226
_reflns_number_gt                1778
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker APEX-II'
_computing_data_reduction        'Briker APEX-II'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Structure solved by direct methods to reveal non-H atoms and remaining non-H
 located in subsequent difference maps. Cu(1) located on a special position
 and coordinated solvent to Cu(1) modelled as a 50:50 mixture of MeOH and    EtOH. H atoms added at calculated positions. The NO3- anion was modelled over two sites related via rocking about O11/O12 with N11 and O13 refined isotropically.

;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0535P)²+18.1832P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2226
_refine_ls_number_parameters     261
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0495
_refine_ls_wR_factor_ref         0.1197
_refine_ls_wR_factor_gt          0.1112
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.145
_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 0.0000 0.38310(14) 0.2500 0.0188(3) Uani 1 2 d S T P . .
N1 N -0.2463(2) 0.3932(6) 0.0689(2) 0.0182(11) Uani 1 1 d . . . . .
O1 O 0.02069(17) 0.2332(6) 0.0786(2) 0.0239(10) Uani 1 1 d . . . . .
C1 C -0.2770(3) 0.3277(8) 0.1037(3) 0.0233(15) Uani 1 1 d . . . . .
H1 H -0.2535 0.2758 0.1491 0.028 Uiso 1 1 calc R U . . .
N2 N -0.1799(2) 0.5250(6) 0.0142(2) 0.0192(12) Uani 1 1 d . . . . .
Cu2 Cu -0.15228(3) 0.39115(10) 0.10185(4) 0.0215(3) Uani 1 1 d . . . . .
O2 O 0.13310(17) 0.2247(5) 0.32479(18) 0.0181(9) Uani 1 1 d . . . . .
C14 C 0.1299(3) 0.0932(8) 0.2031(3) 0.0229(15) Uani 1 1 d . . . . .
H14A H 0.1696 0.1576 0.2207 0.034 Uiso 1 1 calc R U . . .
H14B H 0.1172 0.0542 0.1543 0.034 Uiso 1 1 calc R U . . .
H14C H 0.1350 -0.0109 0.2332 0.034 Uiso 1 1 calc R U . . .
C2 C -0.3418(3) 0.3330(8) 0.0758(3) 0.0267(16) Uani 1 1 d . . . . .
H2 H -0.3622 0.2830 0.1011 0.032 Uiso 1 1 calc R U . . .
C3 C -0.3756(3) 0.4126(8) 0.0107(3) 0.0268(16) Uani 1 1 d . . . . .
H3 H -0.4198 0.4192 -0.0092 0.032 Uiso 1 1 calc R U . . .
N3 N -0.0229(2) 0.6117(7) 0.0480(2) 0.0212(12) Uani 1 1 d . . . . .
H3A H 0.0149 0.5903 0.0820 0.025 Uiso 1 1 calc R U . . .
H3B H -0.0280 0.6843 0.0132 0.025 Uiso 1 1 calc R U . . .
N4 N -0.0715(2) 0.4236(7) 0.0979(3) 0.0236(13) Uani 1 1 d . . . . .
C4 C -0.3450(3) 0.4833(8) -0.0261(3) 0.0263(16) Uani 1 1 d . . . . .
H4 H -0.3678 0.5382 -0.0711 0.032 Uiso 1 1 calc R U . . .
N5 N -0.0139(2) 0.3694(7) 0.1535(2) 0.0191(12) Uani 1 1 d . . . . .
C5 C -0.2800(3) 0.4715(8) 0.0048(3) 0.0189(14) Uani 1 1 d . . . . .
C13 C 0.0808(3) 0.2135(8) 0.2050(3) 0.0169(14) Uani 1 1 d . . . . .
C6 C -0.2414(3) 0.5428(8) -0.0282(3) 0.0202(14) Uani 1 1 d . . . . .
C7 C -0.2619(3) 0.6192(8) -0.0954(3) 0.0228(15) Uani 1 1 d . . . . .
H7 H -0.3052 0.6334 -0.1259 0.027 Uiso 1 1 calc R U . . .
C8 C -0.2177(3) 0.6736(8) -0.1164(3) 0.0223(15) Uani 1 1 d . . . . .
H8 H -0.2307 0.7260 -0.1618 0.027 Uiso 1 1 calc R U . . .
C9 C -0.1543(3) 0.6521(8) -0.0716(3) 0.0221(15) Uani 1 1 d . . . . .
H9 H -0.1239 0.6885 -0.0860 0.026 Uiso 1 1 calc R U . . .
C10 C -0.1367(3) 0.5769(7) -0.0060(3) 0.0174(14) Uani 1 1 d . . . . .
C11 C -0.0719(3) 0.5347(8) 0.0495(3) 0.0174(14) Uani 1 1 d . . . . .
C12 C 0.0252(3) 0.2727(8) 0.1384(3) 0.0183(14) Uani 1 1 d . . . . .
N6 N 0.0827(2) 0.2726(6) 0.2637(2) 0.0159(11) Uani 1 1 d . . . . .
O1S O 0.0382(5) 0.6587(13) 0.2799(5) 0.054(3) Uiso 0.25 1 d D . P A -1
H1S H 0.0826 0.6629 0.3021 0.065 Uiso 0.25 1 calc R U P A -1
C1S C 0.0099(7) 0.8301(14) 0.2726(5) 0.038(4) Uiso 0.25 1 d D . P A -1
H1SA H 0.0417 0.9210 0.2996 0.045 Uiso 0.25 1 calc DR U P A -1
H1SB H -0.0221 0.8279 0.2898 0.045 Uiso 0.25 1 calc DR U P A -1
C2S C -0.0198(11) 0.870(3) 0.1929(7) 0.024(6) Uiso 0.25 1 d D . P A -1
H2SA H -0.0418 0.9842 0.1836 0.037 Uiso 0.25 1 calc . U P B -1
H2SB H -0.0495 0.7755 0.1670 0.037 Uiso 0.25 1 calc . U P C -1
H2SC H 0.0128 0.8756 0.1772 0.037 Uiso 0.25 1 calc . U P D -1
O2S O 0.0382(5) 0.6587(13) 0.2799(5) 0.054(3) Uiso 0.25 1 d D . P A -2
H2S H 0.0826 0.6629 0.3021 0.065 Uiso 0.25 1 calc R U P A -2
C3S C 0.0099(7) 0.8301(14) 0.2726(5) 0.038(4) Uiso 0.25 1 d D . P A -2
H3S1 H 0.0032 0.8545 0.3142 0.056 Uiso 0.25 1 calc . U P E -2
H3S2 H -0.0303 0.8319 0.2298 0.056 Uiso 0.25 1 calc . U P F -2
H3S3 H 0.0374 0.9213 0.2687 0.056 Uiso 0.25 1 calc . U P G -2
O11 O 0.1041(2) 0.6246(7) 0.1755(3) 0.0601(17) Uani 1 1 d D . . . .
O12 O 0.1425(3) 0.6333(7) 0.2904(3) 0.077(2) Uani 1 1 d D . . . .
N11 N 0.1432(5) 0.5956(16) 0.2385(6) 0.039(2) Uiso 0.566(12) 1 d D . P H 1
O13 O 0.1950(4) 0.5300(14) 0.2487(5) 0.0411(19) Uiso 0.566(12) 1 d D . P H 1
N11A N 0.1556(6) 0.6144(19) 0.2289(7) 0.039(2) Uiso 0.434(12) 1 d D . P H 2
O13A O 0.2064(5) 0.5873(18) 0.2281(7) 0.0411(19) Uiso 0.434(12) 1 d D . P H 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N5 1.914(5) . ?
Cu1 N5 1.914(5) 2 ?
Cu1 N6 2.049(5) 2 ?
Cu1 N6 2.049(5) . ?
Cu1 O1S 2.238(10) . ?
N1 C1 1.349(7) . ?
N1 C5 1.359(7) . ?
N1 Cu2 2.039(5) . ?
O1 C12 1.254(7) . ?
C1 C2 1.392(8) . ?
C1 H1 0.9500 . ?
N2 C6 1.343(7) . ?
N2 C10 1.346(7) . ?
N2 Cu2 1.942(5) . ?
Cu2 O2 1.881(4) 2 ?
Cu2 N4 1.994(5) . ?
O2 N6 1.360(5) . ?
O2 Cu2 1.881(4) 2 ?
C14 C13 1.500(8) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C2 C3 1.380(9) . ?
C2 H2 0.9500 . ?
C3 C4 1.394(9) . ?
C3 H3 0.9500 . ?
N3 C11 1.323(7) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N4 C11 1.318(7) . ?
N4 N5 1.410(6) . ?
C4 C5 1.397(8) . ?
C4 H4 0.9500 . ?
N5 C12 1.336(7) . ?
C5 C6 1.487(8) . ?
C13 N6 1.298(7) . ?
C13 C12 1.506(8) . ?
C6 C7 1.400(8) . ?
C7 C8 1.384(8) . ?
C7 H7 0.9500 . ?
C8 C9 1.392(8) . ?
C8 H8 0.9500 . ?
C9 C10 1.374(8) . ?
C9 H9 0.9500 . ?
C10 C11 1.500(8) . ?
O1S C1S 1.432(7) . ?
O1S H1S 0.9500 . ?
C1S C2S 1.532(10) . ?
C1S H1SA 0.9900 . ?
C1S H1SB 0.9900 . ?
C2S H2SA 0.9800 . ?
C2S H2SB 0.9800 . ?
C2S H2SC 0.9800 . ?
O11 N11A 1.243(13) . ?
O11 N11 1.253(11) . ?
O12 N11 1.140(11) . ?
O12 N11A 1.473(14) . ?
N11 O13 1.261(12) . ?
N11A O13A 1.245(13) . ?

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
N5 Cu1 N5 173.8(3) . 2 ?
N5 Cu1 N6 97.82(18) . 2 ?
N5 Cu1 N6 79.65(18) 2 2 ?
N5 Cu1 N6 79.65(18) . . ?
N5 Cu1 N6 97.82(18) 2 . ?
N6 Cu1 N6 132.2(3) 2 . ?
N5 Cu1 O1S 101.7(3) . . ?
N5 Cu1 O1S 84.1(3) 2 . ?
N6 Cu1 O1S 131.5(3) 2 . ?
N6 Cu1 O1S 95.0(3) . . ?
C1 N1 C5 118.4(5) . . ?
C1 N1 Cu2 127.2(4) . . ?
C5 N1 Cu2 114.3(4) . . ?
N1 C1 C2 122.8(6) . . ?
N1 C1 H1 118.6 . . ?
C2 C1 H1 118.6 . . ?
C6 N2 C10 122.1(5) . . ?
C6 N2 Cu2 119.2(4) . . ?
C10 N2 Cu2 118.2(4) . . ?
O2 Cu2 N2 169.04(18) 2 . ?
O2 Cu2 N4 103.61(18) 2 . ?
N2 Cu2 N4 79.4(2) . . ?
O2 Cu2 N1 96.18(17) 2 . ?
N2 Cu2 N1 79.72(19) . . ?
N4 Cu2 N1 158.80(19) . . ?
N6 O2 Cu2 112.9(3) . 2 ?
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 . . ?
C3 C2 C1 118.3(6) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 120.2(6) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C11 N3 H3A 120.0 . . ?
C11 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
C11 N4 N5 119.4(5) . . ?
C11 N4 Cu2 116.4(4) . . ?
N5 N4 Cu2 122.3(4) . . ?
C3 C4 C5 118.3(6) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
C12 N5 N4 119.2(5) . . ?
C12 N5 Cu1 118.7(4) . . ?
N4 N5 Cu1 120.4(3) . . ?
N1 C5 C4 122.0(5) . . ?
N1 C5 C6 114.0(5) . . ?
C4 C5 C6 124.0(5) . . ?
N6 C13 C14 122.8(5) . . ?
N6 C13 C12 115.2(5) . . ?
C14 C13 C12 122.0(5) . . ?
N2 C6 C7 119.7(5) . . ?
N2 C6 C5 112.4(5) . . ?
C7 C6 C5 127.9(5) . . ?
C8 C7 C6 118.5(6) . . ?
C8 C7 H7 120.7 . . ?
C6 C7 H7 120.7 . . ?
C7 C8 C9 120.5(6) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
C10 C9 C8 118.6(6) . . ?
C10 C9 H9 120.7 . . ?
C8 C9 H9 120.7 . . ?
N2 C10 C9 120.6(5) . . ?
N2 C10 C11 111.5(5) . . ?
C9 C10 C11 127.8(5) . . ?
N4 C11 N3 126.9(5) . . ?
N4 C11 C10 112.4(5) . . ?
N3 C11 C10 120.6(5) . . ?
O1 C12 N5 128.4(5) . . ?
O1 C12 C13 120.5(5) . . ?
N5 C12 C13 111.1(5) . . ?
C13 N6 O2 116.7(4) . . ?
C13 N6 Cu1 113.0(4) . . ?
O2 N6 Cu1 129.1(3) . . ?
C1S O1S Cu1 133.5(9) . . ?
C1S O1S H1S 113.2 . . ?
Cu1 O1S H1S 113.2 . . ?
O1S C1S C2S 104.9(12) . . ?
O1S C1S H1SA 110.8 . . ?
C2S C1S H1SA 110.8 . . ?
O1S C1S H1SB 110.8 . . ?
C2S C1S H1SB 110.8 . . ?
H1SA C1S H1SB 108.8 . . ?
C1S C2S H2SA 109.5 . . ?
C1S C2S H2SB 109.5 . . ?
H2SA C2S H2SB 109.5 . . ?
C1S C2S H2SC 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 109.5 . . ?
O12 N11 O11 130.5(11) . . ?
O12 N11 O13 111.9(10) . . ?
O11 N11 O13 117.2(10) . . ?
O11 N11A O13A 125.2(12) . . ?
O11 N11A O12 106.0(10) . . ?
O13A N11A O12 128.8(12) . . ?

_refine_diff_density_max         0.738
_refine_diff_density_min         -0.607
_refine_diff_density_rms         0.105

_shelxl_version_number           2013-3

####################################################################### 
# 
# 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_compound_3
_database_code_depnum_ccdc_archive 'CCDC 1520629'
_audit_update_record             
;
2016-12-04 deposited with the CCDC.
2017-01-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        'Compound 3'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C32 H42 Cu3 N12 O8, 4 (N O3)'
_chemical_formula_sum            'C32 H42 Cu3 N16 O20'
_chemical_formula_weight         1161.43

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 '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                   8.026(4)
_cell_length_b                   12.141(7)
_cell_length_c                   14.647(8)
_cell_angle_alpha                68.018(6)
_cell_angle_beta                 87.679(7)
_cell_angle_gamma                74.002(7)
_cell_volume                     1269.2(12)
_cell_formula_units_Z            1
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4519
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      27.71

_exptl_crystal_description       needle
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_F_000             593
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.331
_shelx_estimated_absorpt_T_min   0.691
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.6908
_exptl_absorpt_correction_T_max  0.9739
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
SADABS 2012/1, Bruker AXS Wisconsin, USA 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13058
_diffrn_reflns_av_unetI/netI     0.0640
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.646
_diffrn_reflns_theta_max         27.494
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             5587
_reflns_number_gt                4534
_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.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Structure solved by direct methods to reveal most non-H atoms. Remaining 
non-H located in subsequent difference maps. One N atom exhibited elongated
U(ij) and was refined isotropically over two positions.
Poorly resolved residual electron density (ca 3e/A3 peaks) was treated with
SQUEEZE within Platon to give small improvements in R1 and wR2 as well as 
reduced residual electron density.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0671P)²+4.3401P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5587
_refine_ls_number_parameters     311
_refine_ls_number_restraints     18
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0634
_refine_ls_wR_factor_ref         0.1578
_refine_ls_wR_factor_gt          0.1492
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.097
_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 0.65390(7) 0.63572(5) 0.16911(4) 0.00975(15) Uani 1 1 d . . . . .
Cu2 Cu 0.5000 0.5000 0.5000 0.0138(2) Uani 1 2 d S . P . .
N11 N 0.6787(5) 0.7084(3) 0.0252(3) 0.0116(7) Uani 1 1 d . . . . .
C11 C 0.8025(7) 0.6659(4) -0.0267(3) 0.0182(6) Uani 1 1 d . U . . .
H11 H 0.8926 0.5927 0.0071 0.022 Uiso 1 1 calc R U . . .
N12 N 0.4254(4) 0.7633(3) 0.1339(3) 0.0100(7) Uani 1 1 d . . . . .
C12 C 0.8049(7) 0.7238(4) -0.1276(3) 0.0182(6) Uani 1 1 d . U . . .
H12 H 0.8942 0.6908 -0.1626 0.022 Uiso 1 1 calc R U . . .
N13 N 0.1629(5) 0.6980(4) 0.3417(3) 0.0221(10) Uani 1 1 d . . . . .
H13A H 0.1549 0.6429 0.4001 0.026 Uiso 1 1 calc R U . . .
H13B H 0.0708 0.7589 0.3106 0.026 Uiso 1 1 calc R U . . .
C13 C 0.6741(6) 0.8311(4) -0.1768(3) 0.0182(6) Uani 1 1 d . U . . .
H13 H 0.6741 0.8742 -0.2459 0.022 Uiso 1 1 calc R U . . .
N14 N 0.4536(14) 0.592(3) 0.3518(8) 0.0053(10) Uiso 0.47(9) 1 d D U P A 1
N15 N 0.6140(14) 0.600(2) 0.3089(10) 0.0054(10) Uiso 0.47(9) 1 d D U P A 1
N14A N 0.4530(12) 0.614(2) 0.3515(7) 0.0053(10) Uiso 0.53(9) 1 d D U P A 2
N15A N 0.6090(15) 0.5841(18) 0.3063(8) 0.0054(10) Uiso 0.53(9) 1 d D U P A 2
C14 C 0.5423(6) 0.8750(4) -0.1233(3) 0.0173(10) Uani 1 1 d . U . . .
H14 H 0.4502 0.9475 -0.1556 0.021 Uiso 1 1 calc R U . . .
C15 C 0.5484(6) 0.8107(4) -0.0225(3) 0.0123(9) Uani 1 1 d . U . . .
N16 N 0.9040(5) 0.5561(3) 0.2301(3) 0.0114(7) Uani 1 1 d . . . . .
C16 C 0.4129(6) 0.8476(4) 0.0405(3) 0.0123(9) Uani 1 1 d . U . . .
C17 C 0.2831(6) 0.9593(4) 0.0083(3) 0.0151(9) Uani 1 1 d . U . . .
H17 H 0.2749 1.0172 -0.0576 0.018 Uiso 1 1 calc R U . . .
C18 C 0.1652(6) 0.9840(4) 0.0755(3) 0.0159(9) Uani 1 1 d . U . . .
H18 H 0.0774 1.0608 0.0564 0.019 Uiso 1 1 calc R U . . .
C19 C 0.1763(6) 0.8966(4) 0.1697(3) 0.0156(9) Uani 1 1 d . U . . .
H19 H 0.0952 0.9124 0.2155 0.019 Uiso 1 1 calc R U . . .
C20 C 0.3080(5) 0.7844(4) 0.1977(3) 0.0106(8) Uani 1 1 d . U . . .
C21 C 0.3157(6) 0.6889(4) 0.2999(3) 0.0122(9) Uani 1 1 d . . . . .
N21 N 1.1711(5) 0.7056(4) -0.0249(3) 0.0171(8) Uani 1 1 d . . . . .
O21 O 1.2287(5) 0.5927(3) -0.0107(3) 0.0315(9) Uani 1 1 d . . . . .
C22 C 0.7448(5) 0.5185(4) 0.3694(3) 0.0107(8) Uani 1 1 d . . . . .
O22 O 1.1897(5) 0.7873(3) -0.1023(3) 0.0288(9) Uani 1 1 d . . . . .
C23 C 0.9137(5) 0.4962(4) 0.3238(3) 0.0112(9) Uani 1 1 d . . . . .
O23 O 1.0900(4) 0.7341(3) 0.0436(2) 0.0182(7) Uani 1 1 d . . . . .
C24 C 1.0732(6) 0.4086(5) 0.3860(4) 0.0256(12) Uani 1 1 d . . . . .
H24A H 1.1761 0.4240 0.3509 0.038 Uiso 1 1 calc R U . . .
H24B H 1.0720 0.3234 0.3997 0.038 Uiso 1 1 calc R U . . .
H24C H 1.0763 0.4208 0.4483 0.038 Uiso 1 1 calc R U . . .
N31 N 0.7156(5) 0.8214(4) 0.3064(3) 0.0189(9) Uani 1 1 d . . . . .
O31 O 0.8096(5) 0.8398(4) 0.2347(3) 0.0326(9) Uani 1 1 d . . . . .
O32 O 0.5565(4) 0.8659(3) 0.2943(3) 0.0303(9) Uani 1 1 d . . . . .
O33 O 0.7873(5) 0.7533(4) 0.3919(3) 0.0297(9) Uani 1 1 d . . . . .
O41 O 0.5258(5) 0.6848(3) 0.5197(3) 0.0255(8) Uani 1 1 d . . . . .
H41 H 0.6386 0.6880 0.5336 0.031 Uiso 1 1 calc R U . . .
C41 C 0.3826(9) 0.7882(6) 0.5118(6) 0.0495(18) Uani 1 1 d . . . . .
H41A H 0.3335 0.8300 0.4433 0.074 Uiso 1 1 calc R U . . .
H41B H 0.4218 0.8460 0.5319 0.074 Uiso 1 1 calc R U . . .
H41C H 0.2936 0.7600 0.5548 0.074 Uiso 1 1 calc R U . . .
O51 O 0.7383(4) 0.4674(3) 0.4624(2) 0.0162(7) Uani 1 1 d . . . . .
O61 O 0.6392(5) 0.4583(3) 0.1696(3) 0.0269(8) Uani 1 1 d . . . . .
H61 H 0.7288 0.4160 0.1402 0.032 Uiso 1 1 calc R U . . .
C61 C 0.5068(8) 0.4016(6) 0.2101(5) 0.0336(14) Uani 1 1 d . . . . .
H61A H 0.4744 0.4147 0.2713 0.050 Uiso 1 1 calc R U . . .
H61B H 0.5493 0.3126 0.2244 0.050 Uiso 1 1 calc R U . . .
H61C H 0.4051 0.4382 0.1628 0.050 Uiso 1 1 calc R U . . .
O52 O 1.0587(4) 0.5305(3) 0.1864(2) 0.0197(7) Uani 1 1 d . . . . .
H52 H 1.0631 0.5936 0.1374 0.030 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N15A 1.919(10) . ?
Cu1 N15 1.960(14) . ?
Cu1 N11 1.984(4) . ?
Cu1 N12 1.986(4) . ?
Cu1 N16 2.047(4) . ?
Cu1 O61 2.187(4) . ?
Cu2 O51 1.944(3) . ?
Cu2 O51 1.944(3) 2_666 ?
Cu2 N14 2.030(11) 2_666 ?
Cu2 N14 2.030(11) . ?
Cu2 N14A 2.078(12) . ?
Cu2 N14A 2.078(12) 2_666 ?
Cu2 O41 2.430(4) . ?
Cu2 O41 2.430(4) 2_666 ?
N11 C11 1.335(6) . ?
N11 C15 1.348(5) . ?
C11 C12 1.380(6) . ?
C11 H11 0.9500 . ?
N12 C20 1.342(6) . ?
N12 C16 1.354(5) . ?
C12 C13 1.387(7) . ?
C12 H12 0.9500 . ?
N13 C21 1.344(6) . ?
N13 H13A 0.8800 . ?
N13 H13B 0.8800 . ?
C13 C14 1.396(7) . ?
C13 H13 0.9500 . ?
N14 C21 1.366(18) . ?
N14 N15 1.421(11) . ?
N15 C22 1.310(13) . ?
N14A C21 1.270(12) . ?
N14A N15A 1.414(10) . ?
N15A C22 1.315(12) . ?
C14 C15 1.384(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.480(6) . ?
N16 C23 1.285(6) . ?
N16 O52 1.385(5) . ?
C16 C17 1.389(6) . ?
C17 C18 1.393(7) . ?
C17 H17 0.9500 . ?
C18 C19 1.379(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.402(6) . ?
C19 H19 0.9500 . ?
C20 C21 1.502(6) . ?
N21 O22 1.232(5) . ?
N21 O21 1.257(5) . ?
N21 O23 1.277(5) . ?
C22 O51 1.275(5) . ?
C22 C23 1.488(6) . ?
C23 C24 1.489(6) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
N31 O32 1.233(5) . ?
N31 O31 1.255(5) . ?
N31 O33 1.266(5) . ?
O41 C41 1.421(7) . ?
O41 H41 0.9500 . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
O61 C61 1.414(6) . ?
O61 H61 0.9500 . ?
C61 H61A 0.9800 . ?
C61 H61B 0.9800 . ?
C61 H61C 0.9800 . ?
O52 H52 0.8400 . ?

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
N15A Cu1 N11 173.0(5) . . ?
N15 Cu1 N11 167.9(7) . . ?
N15A Cu1 N12 90.6(3) . . ?
N15 Cu1 N12 89.0(4) . . ?
N11 Cu1 N12 82.87(15) . . ?
N15A Cu1 N16 80.6(4) . . ?
N15 Cu1 N16 79.7(3) . . ?
N11 Cu1 N16 104.37(15) . . ?
N12 Cu1 N16 155.49(15) . . ?
N15A Cu1 O61 89.9(7) . . ?
N15 Cu1 O61 96.4(8) . . ?
N11 Cu1 O61 94.94(14) . . ?
N12 Cu1 O61 112.52(15) . . ?
N16 Cu1 O61 90.44(15) . . ?
O51 Cu2 O51 180.0 . 2_666 ?
O51 Cu2 N14 98.8(3) . 2_666 ?
O51 Cu2 N14 81.2(3) 2_666 2_666 ?
O51 Cu2 N14 81.2(3) . . ?
O51 Cu2 N14 98.8(3) 2_666 . ?
N14 Cu2 N14 180.0 2_666 . ?
O51 Cu2 N14A 81.8(3) . . ?
O51 Cu2 N14A 98.2(3) 2_666 . ?
O51 Cu2 N14A 98.2(3) . 2_666 ?
O51 Cu2 N14A 81.8(3) 2_666 2_666 ?
N14A Cu2 N14A 180.0 . 2_666 ?
O51 Cu2 O41 89.72(13) . . ?
O51 Cu2 O41 90.28(13) 2_666 . ?
N14 Cu2 O41 89.0(9) 2_666 . ?
N14 Cu2 O41 91.0(9) . . ?
N14A Cu2 O41 83.8(7) . . ?
N14A Cu2 O41 96.2(7) 2_666 . ?
O51 Cu2 O41 90.28(13) . 2_666 ?
O51 Cu2 O41 89.72(13) 2_666 2_666 ?
N14 Cu2 O41 91.0(9) 2_666 2_666 ?
N14 Cu2 O41 89.0(9) . 2_666 ?
N14A Cu2 O41 96.2(7) . 2_666 ?
N14A Cu2 O41 83.8(7) 2_666 2_666 ?
O41 Cu2 O41 180.0 . 2_666 ?
C11 N11 C15 119.1(4) . . ?
C11 N11 Cu1 127.8(3) . . ?
C15 N11 Cu1 113.0(3) . . ?
N11 C11 C12 122.7(5) . . ?
N11 C11 H11 118.7 . . ?
C12 C11 H11 118.7 . . ?
C20 N12 C16 120.4(4) . . ?
C20 N12 Cu1 125.6(3) . . ?
C16 N12 Cu1 112.4(3) . . ?
C11 C12 C13 118.6(5) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
C21 N13 H13A 120.0 . . ?
C21 N13 H13B 120.0 . . ?
H13A N13 H13B 120.0 . . ?
C12 C13 C14 119.2(4) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 H13 120.4 . . ?
C21 N14 N15 113.1(16) . . ?
C21 N14 Cu2 129.1(11) . . ?
N15 N14 Cu2 108.9(8) . . ?
C22 N15 N14 110.7(12) . . ?
C22 N15 Cu1 113.9(9) . . ?
N14 N15 Cu1 125.3(13) . . ?
C21 N14A N15A 120.7(9) . . ?
C21 N14A Cu2 132.4(6) . . ?
N15A N14A Cu2 106.4(9) . . ?
C22 N15A N14A 113.7(9) . . ?
C22 N15A Cu1 116.2(6) . . ?
N14A N15A Cu1 129.9(8) . . ?
C15 C14 C13 118.7(4) . . ?
C15 C14 H14 120.7 . . ?
C13 C14 H14 120.7 . . ?
N11 C15 C14 121.8(4) . . ?
N11 C15 C16 115.3(4) . . ?
C14 C15 C16 123.0(4) . . ?
C23 N16 O52 114.2(3) . . ?
C23 N16 Cu1 113.2(3) . . ?
O52 N16 Cu1 130.5(3) . . ?
N12 C16 C17 121.7(4) . . ?
N12 C16 C15 114.5(4) . . ?
C17 C16 C15 123.7(4) . . ?
C16 C17 C18 118.2(4) . . ?
C16 C17 H17 120.9 . . ?
C18 C17 H17 120.9 . . ?
C19 C18 C17 119.7(4) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 119.7(4) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
N12 C20 C19 120.2(4) . . ?
N12 C20 C21 120.8(4) . . ?
C19 C20 C21 119.0(4) . . ?
N14A C21 N13 119.3(6) . . ?
N13 C21 N14 117.2(6) . . ?
N14A C21 C20 125.8(7) . . ?
N13 C21 C20 114.3(4) . . ?
N14 C21 C20 128.4(6) . . ?
O22 N21 O21 121.8(4) . . ?
O22 N21 O23 120.3(4) . . ?
O21 N21 O23 117.9(4) . . ?
O51 C22 N15 124.6(6) . . ?
O51 C22 N15A 124.9(6) . . ?
O51 C22 C23 119.9(4) . . ?
N15 C22 C23 115.2(6) . . ?
N15A C22 C23 114.9(5) . . ?
N16 C23 C22 113.9(4) . . ?
N16 C23 C24 126.0(4) . . ?
C22 C23 C24 120.1(4) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
O32 N31 O31 121.2(4) . . ?
O32 N31 O33 120.3(4) . . ?
O31 N31 O33 118.5(4) . . ?
C41 O41 Cu2 124.0(4) . . ?
C41 O41 H41 118.0 . . ?
Cu2 O41 H41 118.0 . . ?
O41 C41 H41A 109.5 . . ?
O41 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
O41 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C22 O51 Cu2 111.1(3) . . ?
C61 O61 Cu1 125.2(3) . . ?
C61 O61 H61 117.4 . . ?
Cu1 O61 H61 117.4 . . ?
O61 C61 H61A 109.5 . . ?
O61 C61 H61B 109.5 . . ?
H61A C61 H61B 109.5 . . ?
O61 C61 H61C 109.5 . . ?
H61A C61 H61C 109.5 . . ?
H61B C61 H61C 109.5 . . ?
N16 O52 H52 109.5 . . ?

_refine_diff_density_max         0.792
_refine_diff_density_min         -1.116
_refine_diff_density_rms         0.130

_shelxl_version_number           2013-3


# SQUEEZE RESULTS (Version = 301214)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.002 0.000 0.500 192 87 ' '
# Missing Reflections Below sin(th)/lambda= 0.25
loop_
_platon_missing_refln_index_h
_platon_missing_refln_index_k
_platon_missing_refln_index_l
_platon_missing_refln_theta
0 1 1 1.916
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          
;
TITL MUA721_0m P -1         R = 0.08
CELL    8.0260   12.1410   14.6470     68.02     87.68     74.00
SPGR P-1
# Solvent Accessible Volume =     198.5
# Electrons Found in S.A.V. =      86.6
# Note: Atoms in Void as Cxxx and Qxxx all others
C101 0.936 0.037 0.357 !       4.26 eA-3
C102 0.906 0.938 0.439 !       2.68 eA-3
C103 0.022 0.121 0.358 !       2.67 eA-3
C104 0.924 0.231 0.310 !       1.77 eA-3
C105 0.902 0.110 0.385 !       1.46 eA-3
C106 0.954 0.011 0.418 !       1.30 eA-3
C107 0.045 0.047 0.422 !       1.25 eA-3
C108 0.182 0.052 0.422 !       1.20 eA-3
C109 1.010 0.951 0.484 !       1.10 eA-3
C110 0.500 1.000 0.500 !       1.09 eA-3
C111 0.306 0.142 0.454 !       1.09 eA-3
C112 0.354 0.052 0.464 !       1.04 eA-3
C113 0.973 0.123 0.430 !       1.04 eA-3
C114 0.982 0.114 0.503 !       1.04 eA-3
Q115 0.428 0.969 0.405 !       1.03 eA-3
C116 0.104 0.071 0.467 !       1.00 eA-3
C117 0.191 0.094 0.465 !       0.99 eA-3
C118 0.100 0.064 0.312 !       0.98 eA-3
Q119 0.608 0.122 0.372 !       0.98 eA-3
C120 0.265 0.094 0.423 !       0.97 eA-3
C121 0.494 0.089 0.391 !       0.96 eA-3
Q122 0.222 0.951 0.483 !       0.96 eA-3
Q123 0.090 0.048 0.250 !       0.95 eA-3
C124 0.218 0.123 0.356 !       0.95 eA-3
Q125 0.735 0.078 0.392 !       0.92 eA-3
Q126 0.285 0.981 0.393 !       0.92 eA-3
C127 0.604 0.048 0.406 !       0.92 eA-3
Q128 0.174 0.935 0.374 !       0.92 eA-3
C129 0.128 0.999 0.500 !       0.91 eA-3
Q130 0.152 0.219 0.312 !       0.91 eA-3
Q131 0.552 0.113 0.309 !       0.89 eA-3
Q132 0.682 0.855 0.469 !       0.89 eA-3
C133 0.386 0.120 0.405 !       0.88 eA-3
Q134 0.216 0.159 0.175 !       0.86 eA-3
Q135 0.789 0.058 0.450 !       0.85 eA-3
C136 0.904 0.060 0.468 !       0.85 eA-3
Q137 0.423 0.062 0.343 !       0.85 eA-3
Q138 0.631 0.146 0.481 !       0.85 eA-3
Q139 0.811 0.919 0.278 !       0.84 eA-3
Q140 0.472 0.582 0.487 !       0.84 eA-3
Q141 0.698 0.217 0.380 !       0.84 eA-3
C142 0.081 0.953 0.440 !       0.83 eA-3
C143 0.604 0.922 0.486 !       0.83 eA-3
Q144 0.562 0.065 0.486 !       0.82 eA-3
Q145 0.431 0.876 0.475 !       0.82 eA-3
Q146 0.236 0.843 0.172 !       0.82 eA-3
Q147 0.437 0.531 0.454 !       0.81 eA-3
C148 0.677 0.164 0.325 !       0.80 eA-3
Q149 0.842 0.127 0.452 !       0.80 eA-3
Q150 0.453 0.981 0.466 !       0.80 eA-3
Q151 0.183 0.093 0.232 !       0.79 eA-3
Q152 0.368 0.123 0.156 !       0.79 eA-3
Q153 0.661 0.666 0.112 !       0.79 eA-3
Q154 0.153 0.979 0.419 !       0.79 eA-3
Q155 0.149 0.811 0.486 !       0.79 eA-3
C156 0.580 0.985 0.470 !       0.78 eA-3
Q157 0.658 0.614 0.234 !       0.78 eA-3
Q158 0.860 0.171 0.391 !       0.78 eA-3
Q159 0.813 0.564 0.156 !       0.78 eA-3
Q160 0.187 0.182 0.221 !       0.78 eA-3
Q161 0.192 0.313 0.075 !       0.77 eA-3
Q162 0.506 0.105 0.188 !       0.77 eA-3
Q163 0.092 0.053 0.174 !       0.77 eA-3
Q164 0.378 1.005 0.328 !       0.76 eA-3
Q165 0.783 0.765 0.344 !       0.76 eA-3
Q166 0.331 0.927 0.516 !       0.76 eA-3
Q167 0.226 0.033 0.301 !       0.76 eA-3
Q168 0.447 0.138 0.470 !       0.76 eA-3
Q169 0.590 0.716 0.470 !       0.75 eA-3
C170 0.284 0.101 0.504 !       0.75 eA-3
Q171 0.904 0.825 0.264 !       0.75 eA-3
Q172 0.097 0.137 0.265 !       0.75 eA-3
Q173 0.412 0.916 0.340 !       0.75 eA-3
Q174 0.284 0.923 0.358 !       0.74 eA-3
Q175 0.190 0.877 0.329 !       0.74 eA-3
Q176 0.555 1.005 0.356 !       0.74 eA-3
C177 0.468 0.013 0.434 !       0.74 eA-3
Q178 0.229 0.187 0.466 !       0.73 eA-3
Q179 0.944 0.872 0.388 !       0.73 eA-3
Q180 0.566 0.470 0.125 !       0.73 eA-3
Q181 0.673 0.029 0.452 !       0.73 eA-3
Q182 0.321 0.090 0.328 !       0.72 eA-3
Q183 0.667 0.953 0.409 !       0.72 eA-3
Q184 0.233 0.962 0.049 !       0.72 eA-3
Q185 0.893 0.189 0.458 !       0.72 eA-3
Q186 0.906 0.247 0.502 !       0.72 eA-3
Q187 0.287 0.863 0.473 !       0.72 eA-3
Q188 0.524 0.901 0.454 !       0.72 eA-3
Q189 0.044 0.861 0.333 !       0.71 eA-3
Q190 0.443 0.582 0.403 !       0.71 eA-3
C191 0.156 0.170 0.400 !       0.71 eA-3
Q192 0.784 0.405 0.502 !       0.71 eA-3
Q193 0.830 0.768 0.421 !       0.70 eA-3
Q194 0.369 0.902 0.032 !       0.70 eA-3
Q195 0.525 0.826 0.438 !       0.70 eA-3
Q196 0.853 0.880 0.423 !       0.70 eA-3
Q197 0.623 0.718 0.139 !       0.70 eA-3
Q198 0.190 0.971 0.294 !       0.70 eA-3
Q199 0.342 0.915 0.457 !       0.70 eA-3
;

####################################################################### 
# 
# 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_compound_1
_database_code_depnum_ccdc_archive 'CCDC 1520627'
_audit_update_record             
;
2016-12-04 deposited with the CCDC.
2017-01-30 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2013
_chemical_name_systematic        'Compound 1'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H14 Cl2 Cu N6 O2, 3 (C H4 O)'
_chemical_formula_sum            'C17 H26 Cl2 Cu N6 O5'
_chemical_formula_weight         528.88

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

_space_group_crystal_system      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                   8.350(6)
_cell_length_b                   12.084(9)
_cell_length_c                   12.264(9)
_cell_angle_alpha                68.723(7)
_cell_angle_beta                 89.547(8)
_cell_angle_gamma                87.922(8)
_cell_volume                     1152.3(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5734
_cell_measurement_theta_min      2.99
_cell_measurement_theta_max      27.44

_exptl_crystal_description       needle
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.524
_exptl_crystal_F_000             546
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    1.220
_shelx_estimated_absorpt_T_min   0.654
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5976
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
Sadabs 2012/1 Bruker AXS Madison WI, USA
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II, CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12842
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_av_R_equivalents  0.0324
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.027
_diffrn_reflns_theta_max         27.600
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             5121
_reflns_number_gt                4542
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'


_refine_special_details          
;
 Structure solved using superflip within Crystals. Three H-bonded
methanol solvate molecules located in structure.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0303P)²+2.0918P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     superflip
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5121
_refine_ls_number_parameters     285
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.0992
_refine_ls_wR_factor_gt          0.0959
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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 0.20041(4) 0.52229(3) 0.21854(3) 0.01484(10) Uani 1 1 d . . . . .
Cl2 Cl 0.43959(8) 0.37137(6) 0.31263(6) 0.02003(15) Uani 1 1 d . . . . .
Cl1 Cl 0.15176(9) 0.62214(7) 0.33468(7) 0.02686(17) Uani 1 1 d . . . . .
N4 N 0.3267(3) 0.64337(19) 0.09503(19) 0.0146(4) Uani 1 1 d . . . . .
N5 N 0.3883(3) 0.74732(19) 0.10165(19) 0.0157(5) Uani 1 1 d . . . . .
H5 H 0.4851 0.7480 0.1292 0.019 Uiso 1 1 calc R U . . .
C12 C 0.2910(3) 0.8471(2) 0.0633(2) 0.0163(5) Uani 1 1 d . . . . .
O1 O 0.1724(2) 0.85696(17) 0.00299(18) 0.0239(4) Uani 1 1 d . . . . .
C13 C 0.3450(3) 0.9482(2) 0.0960(2) 0.0157(5) Uani 1 1 d . . . . .
N6 N 0.4745(3) 0.9291(2) 0.1547(2) 0.0174(5) Uani 1 1 d . . . . .
O2 O 0.5205(2) 1.02911(17) 0.17636(18) 0.0223(4) Uani 1 1 d . . . . .
H2A H 0.6045 1.0124 0.2173 0.046(12) Uiso 1 1 calc R . . . .
C14 C 0.2470(3) 1.0620(2) 0.0549(3) 0.0234(6) Uani 1 1 d . . . . .
H14A H 0.2344 1.0916 0.1191 0.035 Uiso 1 1 calc R U . . .
H14B H 0.1412 1.0479 0.0293 0.035 Uiso 1 1 calc R U . . .
H14C H 0.3011 1.1209 -0.0108 0.035 Uiso 1 1 calc R U . . .
C11 C 0.3502(3) 0.6275(2) -0.0035(2) 0.0137(5) Uani 1 1 d . . . . .
N3 N 0.4289(3) 0.6988(2) -0.0950(2) 0.0181(5) Uani 1 1 d . . . . .
H3A H 0.4706 0.7636 -0.0923 0.022 Uiso 1 1 calc R U . . .
H3B H 0.4392 0.6813 -0.1585 0.022 Uiso 1 1 calc R U . . .
C10 C 0.2738(3) 0.5196(2) -0.0081(2) 0.0133(5) Uani 1 1 d . . . . .
N2 N 0.1936(3) 0.46331(19) 0.09005(19) 0.0137(4) Uani 1 1 d . . . . .
C6 C 0.1049(3) 0.3698(2) 0.1022(2) 0.0142(5) Uani 1 1 d . . . . .
C7 C 0.0947(3) 0.3271(2) 0.0108(2) 0.0157(5) Uani 1 1 d . . . . .
H7 H 0.0300 0.2618 0.0176 0.019 Uiso 1 1 calc R U . . .
C8 C 0.1812(3) 0.3824(2) -0.0900(2) 0.0184(6) Uani 1 1 d . . . . .
H8 H 0.1787 0.3531 -0.1521 0.022 Uiso 1 1 calc R U . . .
C9 C 0.2723(3) 0.4807(2) -0.1014(2) 0.0164(5) Uani 1 1 d . . . . .
H9 H 0.3312 0.5194 -0.1706 0.020 Uiso 1 1 calc R U . . .
C5 C 0.0192(3) 0.3256(2) 0.2154(2) 0.0155(5) Uani 1 1 d . . . . .
N1 N 0.0411(3) 0.3908(2) 0.2836(2) 0.0168(5) Uani 1 1 d . . . . .
C1 C -0.0374(4) 0.3631(3) 0.3847(2) 0.0220(6) Uani 1 1 d . . . . .
H1 H -0.0209 0.4082 0.4327 0.026 Uiso 1 1 calc R U . . .
C2 C -0.1425(4) 0.2704(3) 0.4221(3) 0.0253(6) Uani 1 1 d . . . . .
H2 H -0.1988 0.2534 0.4936 0.030 Uiso 1 1 calc R U . . .
C3 C -0.1634(4) 0.2036(3) 0.3532(3) 0.0261(7) Uani 1 1 d . . . . .
H3 H -0.2340 0.1393 0.3774 0.031 Uiso 1 1 calc R U . . .
C4 C -0.0812(3) 0.2306(2) 0.2487(3) 0.0204(6) Uani 1 1 d . . . . .
H4 H -0.0935 0.1847 0.2009 0.024 Uiso 1 1 calc R U . . .
C1S C 0.5963(5) 0.6455(4) 0.4001(3) 0.0410(9) Uani 1 1 d D . . . .
H1S1 H 0.6699 0.5880 0.4559 0.062 Uiso 1 1 calc R U . . .
H1S2 H 0.4893 0.6405 0.4346 0.062 Uiso 1 1 calc R U . . .
H1S3 H 0.6350 0.7259 0.3814 0.062 Uiso 1 1 calc R U . . .
O1S O 0.5885(3) 0.61973(19) 0.29590(18) 0.0261(5) Uani 1 1 d D . . . .
H1S4 H 0.5496 0.5527 0.3111 0.039 Uiso 1 1 calc R U . . .
C2S C 0.9082(5) 0.8986(4) 0.2697(4) 0.0481(10) Uani 1 1 d D . . . .
H2S1 H 0.9296 0.9404 0.1863 0.072 Uiso 1 1 calc R U . . .
H2S2 H 0.8785 0.8171 0.2828 0.072 Uiso 1 1 calc R U . . .
H2S3 H 1.0045 0.8970 0.3154 0.072 Uiso 1 1 calc R U . . .
O2S O 0.7806(3) 0.95857(19) 0.30506(19) 0.0279(5) Uani 1 1 d D . . . .
H2S4 H 0.7542 0.9181 0.3739 0.042 Uiso 1 1 calc R U . . .
C3S C 0.6969(6) 0.9274(4) 0.6075(4) 0.0526(11) Uani 1 1 d D . . . .
H3S1 H 0.6829 0.8725 0.6882 0.079 Uiso 1 1 calc R U . . .
H3S2 H 0.6017 0.9804 0.5826 0.079 Uiso 1 1 calc R U . . .
H3S3 H 0.7914 0.9746 0.6032 0.079 Uiso 1 1 calc R U . . .
O3S O 0.7179(4) 0.8628(2) 0.5343(2) 0.0607(9) Uani 1 1 d D . . . .
H3S4 H 0.7031 0.7906 0.5724 0.091 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N2 1.953(2) . ?
Cu1 N4 2.006(2) . ?
Cu1 N1 2.037(2) . ?
Cu1 Cl1 2.2027(13) . ?
Cu1 Cl2 2.6250(15) . ?
N4 C11 1.302(3) . ?
N4 N5 1.404(3) . ?
N5 C12 1.364(3) . ?
N5 H5 0.8800 . ?
C12 O1 1.217(3) . ?
C12 C13 1.501(4) . ?
C13 N6 1.270(4) . ?
C13 C14 1.495(4) . ?
N6 O2 1.395(3) . ?
O2 H2A 0.8400 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C11 N3 1.327(3) . ?
C11 C10 1.491(4) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
C10 N2 1.337(3) . ?
C10 C9 1.386(4) . ?
N2 C6 1.336(3) . ?
C6 C7 1.398(4) . ?
C6 C5 1.483(4) . ?
C7 C8 1.385(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.398(4) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C5 N1 1.358(3) . ?
C5 C4 1.383(4) . ?
N1 C1 1.335(4) . ?
C1 C2 1.387(4) . ?
C1 H1 0.9500 . ?
C2 C3 1.379(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.386(4) . ?
C3 H3 0.9500 . ?
C4 H4 0.9500 . ?
C1S O1S 1.423(4) . ?
C1S H1S1 0.9800 . ?
C1S H1S2 0.9800 . ?
C1S H1S3 0.9800 . ?
O1S H1S4 0.8400 . ?
C2S O2S 1.419(4) . ?
C2S H2S1 0.9800 . ?
C2S H2S2 0.9800 . ?
C2S H2S3 0.9800 . ?
O2S H2S4 0.8400 . ?
C3S O3S 1.394(4) . ?
C3S H3S1 0.9800 . ?
C3S H3S2 0.9800 . ?
C3S H3S3 0.9800 . ?
O3S H3S4 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 Cu1 N4 78.27(10) . . ?
N2 Cu1 N1 79.77(10) . . ?
N4 Cu1 N1 156.54(9) . . ?
N2 Cu1 Cl1 163.63(7) . . ?
N4 Cu1 Cl1 98.93(8) . . ?
N1 Cu1 Cl1 99.81(8) . . ?
N2 Cu1 Cl2 89.56(7) . . ?
N4 Cu1 Cl2 97.35(8) . . ?
N1 Cu1 Cl2 90.62(9) . . ?
Cl1 Cu1 Cl2 106.81(5) . . ?
C11 N4 N5 115.7(2) . . ?
C11 N4 Cu1 117.60(18) . . ?
N5 N4 Cu1 126.61(17) . . ?
C12 N5 N4 116.8(2) . . ?
C12 N5 H5 121.6 . . ?
N4 N5 H5 121.6 . . ?
O1 C12 N5 123.4(2) . . ?
O1 C12 C13 121.6(2) . . ?
N5 C12 C13 115.0(2) . . ?
N6 C13 C14 125.8(2) . . ?
N6 C13 C12 115.8(2) . . ?
C14 C13 C12 118.4(2) . . ?
C13 N6 O2 112.3(2) . . ?
N6 O2 H2A 109.5 . . ?
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 . . ?
N4 C11 N3 125.9(2) . . ?
N4 C11 C10 113.4(2) . . ?
N3 C11 C10 120.7(2) . . ?
C11 N3 H3A 120.0 . . ?
C11 N3 H3B 120.0 . . ?
H3A N3 H3B 120.0 . . ?
N2 C10 C9 121.0(2) . . ?
N2 C10 C11 111.5(2) . . ?
C9 C10 C11 127.4(2) . . ?
C6 N2 C10 122.2(2) . . ?
C6 N2 Cu1 118.66(18) . . ?
C10 N2 Cu1 119.11(18) . . ?
N2 C6 C7 120.0(2) . . ?
N2 C6 C5 113.0(2) . . ?
C7 C6 C5 126.8(2) . . ?
C8 C7 C6 118.3(2) . . ?
C8 C7 H7 120.9 . . ?
C6 C7 H7 120.9 . . ?
C7 C8 C9 120.8(3) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 H8 119.6 . . ?
C10 C9 C8 117.6(2) . . ?
C10 C9 H9 121.2 . . ?
C8 C9 H9 121.2 . . ?
N1 C5 C4 121.6(3) . . ?
N1 C5 C6 114.0(2) . . ?
C4 C5 C6 124.3(2) . . ?
C1 N1 C5 119.1(2) . . ?
C1 N1 Cu1 126.57(19) . . ?
C5 N1 Cu1 114.27(18) . . ?
N1 C1 C2 122.2(3) . . ?
N1 C1 H1 118.9 . . ?
C2 C1 H1 118.9 . . ?
C3 C2 C1 118.6(3) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 119.8(3) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 118.6(3) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
O1S C1S H1S1 109.5 . . ?
O1S C1S H1S2 109.5 . . ?
H1S1 C1S H1S2 109.5 . . ?
O1S C1S H1S3 109.5 . . ?
H1S1 C1S H1S3 109.5 . . ?
H1S2 C1S H1S3 109.5 . . ?
C1S O1S H1S4 109.5 . . ?
O2S C2S H2S1 109.5 . . ?
O2S C2S H2S2 109.5 . . ?
H2S1 C2S H2S2 109.5 . . ?
O2S C2S H2S3 109.5 . . ?
H2S1 C2S H2S3 109.5 . . ?
H2S2 C2S H2S3 109.5 . . ?
C2S O2S H2S4 109.5 . . ?
O3S C3S H3S1 109.5 . . ?
O3S C3S H3S2 109.5 . . ?
H3S1 C3S H3S2 109.5 . . ?
O3S C3S H3S3 109.5 . . ?
H3S1 C3S H3S3 109.5 . . ?
H3S2 C3S H3S3 109.5 . . ?
C3S O3S H3S4 109.5 . . ?

_refine_diff_density_max         0.982
_refine_diff_density_min         -0.610
_refine_diff_density_rms         0.082

_shelxl_version_number           2013-3

