# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_1phen
_database_code_depnum_ccdc_archive 'CCDC 1520855'
_audit_update_record             
;
2016-12-05 deposited with the CCDC.
2017-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H18 Cu N4 O2'
_chemical_formula_sum            'C26 H18 Cu N4 O2'
_chemical_formula_weight         481.98

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'
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           9
_space_group_name_H-M_alt        'C 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'

_cell_length_a                   17.7697(10)
_cell_length_b                   10.7634(7)
_cell_length_c                   11.4808(6)
_cell_angle_alpha                90
_cell_angle_beta                 103.834(6)
_cell_angle_gamma                90
_cell_volume                     2132.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1257
_cell_measurement_theta_min      4.4630
_cell_measurement_theta_max      23.8620

_exptl_crystal_description       prism
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_F_000             988
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_absorpt_coefficient_mu    1.057
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  0.93423
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5282
_diffrn_reflns_av_unetI/netI     0.0848
_diffrn_reflns_av_R_equivalents  0.0447
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.205
_diffrn_reflns_theta_max         26.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             2969
_reflns_number_gt                2296
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.998
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.995

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 
;

_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY 3.7. (CCDC, 2015)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0465P)²] 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_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.44(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2969
_refine_ls_number_parameters     299
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.0633
_refine_ls_wR_factor_ref         0.1139
_refine_ls_wR_factor_gt          0.1051
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.049
_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 0.52875(7) 0.20935(7) 0.47893(10) 0.0363(2) Uani 1 1 d . . . . .
N1 N 0.5096(3) 0.0544(6) 0.5485(5) 0.0353(14) Uani 1 1 d . . . . .
N2 N 0.4452(4) -0.0112(6) 0.4818(6) 0.0409(15) Uani 1 1 d . . . . .
N3 N 0.5493(3) 0.3729(6) 0.4076(5) 0.0352(14) Uani 1 1 d . . . . .
N4 N 0.4609(4) 0.3431(6) 0.5678(6) 0.0357(15) Uani 1 1 d . . . . .
O1 O 0.4436(3) 0.1475(5) 0.3462(5) 0.0416(13) Uani 1 1 d . . . . .
O2 O 0.6313(3) 0.2214(5) 0.5832(5) 0.0504(15) Uani 1 1 d . . . . .
C1 C 0.4178(4) 0.0440(7) 0.3791(7) 0.0353(16) Uani 1 1 d . . . . .
C2 C 0.3547(4) -0.0222(7) 0.2957(6) 0.0361(17) Uani 1 1 d . . . . .
C3 C 0.3294(4) 0.0154(8) 0.1772(7) 0.049(2) Uani 1 1 d . . . . .
H3 H 0.3500 0.0868 0.1513 0.059 Uiso 1 1 calc R U . . .
C4 C 0.2741(5) -0.0522(10) 0.0974(8) 0.061(3) Uani 1 1 d . . . . .
H4 H 0.2594 -0.0273 0.0176 0.073 Uiso 1 1 calc R U . . .
C5 C 0.2408(5) -0.1543(10) 0.1328(9) 0.061(3) Uani 1 1 d . . . . .
H5 H 0.2032 -0.1985 0.0783 0.073 Uiso 1 1 calc R U . . .
C6 C 0.2636(4) -0.1919(7) 0.2517(9) 0.053(2) Uani 1 1 d . . . . .
H6 H 0.2412 -0.2615 0.2775 0.064 Uiso 1 1 calc R U . . .
C7 C 0.3189(4) -0.1265(8) 0.3302(7) 0.0440(19) Uani 1 1 d . . . . .
H7 H 0.3334 -0.1523 0.4097 0.053 Uiso 1 1 calc R U . . .
C8 C 0.5447(5) 0.0116(7) 0.6502(7) 0.0435(18) Uani 1 1 d . . . . .
H8 H 0.5228 -0.0562 0.6800 0.052 Uiso 1 1 calc R U . . .
C9 C 0.6151(4) 0.0602(7) 0.7216(7) 0.0399(18) Uani 1 1 d . . . . .
C10 C 0.6559(4) 0.1595(8) 0.6815(7) 0.0391(18) Uani 1 1 d . . . . .
C11 C 0.7289(4) 0.1913(9) 0.7569(8) 0.051(2) Uani 1 1 d . . . . .
H11 H 0.7582 0.2523 0.7311 0.062 Uiso 1 1 calc R U . . .
C12 C 0.7578(5) 0.1370(10) 0.8647(9) 0.065(3) Uani 1 1 d . . . . .
H12 H 0.8055 0.1624 0.9114 0.078 Uiso 1 1 calc R U . . .
C13 C 0.7165(6) 0.0426(11) 0.9067(8) 0.071(3) Uani 1 1 d . . . . .
H13 H 0.7355 0.0064 0.9815 0.086 Uiso 1 1 calc R U . . .
C14 C 0.6479(6) 0.0060(10) 0.8346(8) 0.064(3) Uani 1 1 d . . . . .
H14 H 0.6210 -0.0581 0.8609 0.077 Uiso 1 1 calc R U . . .
C15 C 0.5939(4) 0.3876(9) 0.3328(7) 0.047(2) Uani 1 1 d . . . . .
H15 H 0.6122 0.3173 0.3013 0.056 Uiso 1 1 calc R U . . .
C16 C 0.6155(5) 0.5065(9) 0.2977(8) 0.052(2) Uani 1 1 d . . . . .
H16 H 0.6466 0.5139 0.2435 0.062 Uiso 1 1 calc R U . . .
C17 C 0.5900(5) 0.6083(10) 0.3448(8) 0.051(3) Uani 1 1 d . . . . .
H17 H 0.6042 0.6868 0.3240 0.061 Uiso 1 1 calc R U . . .
C18 C 0.5421(4) 0.5963(8) 0.4248(7) 0.0400(19) Uani 1 1 d . . . . .
C19 C 0.5120(5) 0.7008(7) 0.4773(12) 0.053(3) Uani 1 1 d . . . . .
H19 H 0.5251 0.7809 0.4589 0.063 Uiso 1 1 calc R U . . .
C20 C 0.4656(5) 0.6849(8) 0.5519(9) 0.053(2) Uani 1 1 d . . . . .
H20 H 0.4456 0.7545 0.5820 0.064 Uiso 1 1 calc R U . . .
C21 C 0.4460(5) 0.5659(8) 0.5862(8) 0.041(2) Uani 1 1 d . . . . .
C22 C 0.3998(5) 0.5437(9) 0.6674(8) 0.052(2) Uani 1 1 d . . . . .
H22 H 0.3795 0.6100 0.7019 0.062 Uiso 1 1 calc R U . . .
C23 C 0.3849(5) 0.4269(9) 0.6953(7) 0.052(2) Uani 1 1 d . . . . .
H23 H 0.3537 0.4120 0.7483 0.063 Uiso 1 1 calc R U . . .
C24 C 0.4163(4) 0.3279(8) 0.6447(7) 0.046(2) Uani 1 1 d . . . . .
H24 H 0.4056 0.2475 0.6657 0.055 Uiso 1 1 calc R U . . .
C25 C 0.4737(4) 0.4601(7) 0.5374(6) 0.0341(17) Uani 1 1 d . . . . .
C26 C 0.5238(5) 0.4765(6) 0.4542(7) 0.037(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1 1.914(6) . ?
Cu1 O2 1.931(6) . ?
Cu1 O1 1.987(5) . ?
Cu1 N3 2.012(6) . ?
Cu1 N4 2.271(7) . ?
N1 C8 1.272(9) . ?
N1 N2 1.406(8) . ?
N2 C1 1.306(9) . ?
N3 C15 1.310(9) . ?
N3 C26 1.361(10) . ?
N4 C24 1.330(10) . ?
N4 C25 1.341(10) . ?
O1 C1 1.295(9) . ?
O2 C10 1.293(10) . ?
C1 C2 1.473(10) . ?
C2 C3 1.387(10) . ?
C2 C7 1.393(11) . ?
C3 C4 1.380(11) . ?
C3 H3 0.9300 . ?
C4 C5 1.356(13) . ?
C4 H4 0.9300 . ?
C5 C6 1.387(12) . ?
C5 H5 0.9300 . ?
C6 C7 1.360(11) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.421(10) . ?
C8 H8 0.9300 . ?
C9 C14 1.414(11) . ?
C9 C10 1.428(11) . ?
C10 C11 1.418(11) . ?
C11 C12 1.355(12) . ?
C11 H11 0.9300 . ?
C12 C13 1.404(14) . ?
C12 H12 0.9300 . ?
C13 C14 1.358(13) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.421(12) . ?
C15 H15 0.9300 . ?
C16 C17 1.347(13) . ?
C16 H16 0.9300 . ?
C17 C18 1.399(11) . ?
C17 H17 0.9300 . ?
C18 C26 1.391(10) . ?
C18 C19 1.438(13) . ?
C19 C20 1.335(15) . ?
C19 H19 0.9300 . ?
C20 C21 1.409(12) . ?
C20 H20 0.9300 . ?
C21 C22 1.402(12) . ?
C21 C25 1.409(11) . ?
C22 C23 1.339(12) . ?
C22 H22 0.9300 . ?
C23 C24 1.393(11) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 C26 1.464(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 O2 92.0(2) . . ?
N1 Cu1 O1 81.3(2) . . ?
O2 Cu1 O1 158.5(2) . . ?
N1 Cu1 N3 179.4(3) . . ?
O2 Cu1 N3 87.5(2) . . ?
O1 Cu1 N3 99.2(2) . . ?
N1 Cu1 N4 101.5(2) . . ?
O2 Cu1 N4 101.7(2) . . ?
O1 Cu1 N4 99.7(2) . . ?
N3 Cu1 N4 78.2(3) . . ?
C8 N1 N2 118.3(6) . . ?
C8 N1 Cu1 127.0(6) . . ?
N2 N1 Cu1 114.4(4) . . ?
C1 N2 N1 110.0(6) . . ?
C15 N3 C26 118.0(7) . . ?
C15 N3 Cu1 124.7(6) . . ?
C26 N3 Cu1 116.6(5) . . ?
C24 N4 C25 117.0(7) . . ?
C24 N4 Cu1 133.2(5) . . ?
C25 N4 Cu1 109.7(5) . . ?
C1 O1 Cu1 108.8(5) . . ?
C10 O2 Cu1 125.3(5) . . ?
O1 C1 N2 124.9(7) . . ?
O1 C1 C2 119.7(7) . . ?
N2 C1 C2 115.4(7) . . ?
C3 C2 C7 116.8(7) . . ?
C3 C2 C1 120.9(7) . . ?
C7 C2 C1 122.2(7) . . ?
C4 C3 C2 120.6(8) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C5 C4 C3 121.4(9) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 119.1(8) . . ?
C4 C5 H5 120.5 . . ?
C6 C5 H5 120.5 . . ?
C7 C6 C5 119.7(8) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C6 C7 C2 122.4(8) . . ?
C6 C7 H7 118.8 . . ?
C2 C7 H7 118.8 . . ?
N1 C8 C9 124.5(7) . . ?
N1 C8 H8 117.7 . . ?
C9 C8 H8 117.7 . . ?
C14 C9 C8 119.3(8) . . ?
C14 C9 C10 118.3(8) . . ?
C8 C9 C10 122.3(7) . . ?
O2 C10 C11 118.5(8) . . ?
O2 C10 C9 125.1(7) . . ?
C11 C10 C9 116.4(7) . . ?
C12 C11 C10 123.0(9) . . ?
C12 C11 H11 118.5 . . ?
C10 C11 H11 118.5 . . ?
C11 C12 C13 120.7(8) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 117.9(9) . . ?
C14 C13 H13 121.1 . . ?
C12 C13 H13 121.1 . . ?
C13 C14 C9 123.5(10) . . ?
C13 C14 H14 118.2 . . ?
C9 C14 H14 118.2 . . ?
N3 C15 C16 122.7(8) . . ?
N3 C15 H15 118.6 . . ?
C16 C15 H15 118.6 . . ?
C17 C16 C15 118.6(8) . . ?
C17 C16 H16 120.7 . . ?
C15 C16 H16 120.7 . . ?
C16 C17 C18 120.3(8) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C26 C18 C17 117.3(8) . . ?
C26 C18 C19 119.4(8) . . ?
C17 C18 C19 123.2(8) . . ?
C20 C19 C18 121.2(8) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C19 C20 C21 121.9(8) . . ?
C19 C20 H20 119.1 . . ?
C21 C20 H20 119.1 . . ?
C22 C21 C20 124.4(8) . . ?
C22 C21 C25 116.3(8) . . ?
C20 C21 C25 119.4(8) . . ?
C23 C22 C21 120.0(8) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C22 C23 C24 119.8(8) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
N4 C24 C23 122.9(8) . . ?
N4 C24 H24 118.5 . . ?
C23 C24 H24 118.5 . . ?
N4 C25 C21 123.9(7) . . ?
N4 C25 C26 116.8(7) . . ?
C21 C25 C26 119.2(7) . . ?
N3 C26 C18 123.0(8) . . ?
N3 C26 C25 118.0(7) . . ?
C18 C26 C25 119.0(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 N2 C1 -178.4(6) . . . . ?
Cu1 N1 N2 C1 7.0(7) . . . . ?
Cu1 O1 C1 N2 -1.7(8) . . . . ?
Cu1 O1 C1 C2 -179.3(5) . . . . ?
N1 N2 C1 O1 -3.4(9) . . . . ?
N1 N2 C1 C2 174.3(5) . . . . ?
O1 C1 C2 C3 8.7(10) . . . . ?
N2 C1 C2 C3 -169.1(7) . . . . ?
O1 C1 C2 C7 -173.0(7) . . . . ?
N2 C1 C2 C7 9.1(10) . . . . ?
C7 C2 C3 C4 -3.0(11) . . . . ?
C1 C2 C3 C4 175.4(7) . . . . ?
C2 C3 C4 C5 2.4(13) . . . . ?
C3 C4 C5 C6 -0.7(14) . . . . ?
C4 C5 C6 C7 -0.2(13) . . . . ?
C5 C6 C7 C2 -0.5(12) . . . . ?
C3 C2 C7 C6 2.1(11) . . . . ?
C1 C2 C7 C6 -176.2(7) . . . . ?
N2 N1 C8 C9 173.1(6) . . . . ?
Cu1 N1 C8 C9 -13.1(11) . . . . ?
N1 C8 C9 C14 178.8(8) . . . . ?
N1 C8 C9 C10 -3.6(11) . . . . ?
Cu1 O2 C10 C11 -171.2(5) . . . . ?
Cu1 O2 C10 C9 8.7(11) . . . . ?
C14 C9 C10 O2 -176.6(8) . . . . ?
C8 C9 C10 O2 5.7(11) . . . . ?
C14 C9 C10 C11 3.2(10) . . . . ?
C8 C9 C10 C11 -174.4(7) . . . . ?
O2 C10 C11 C12 176.2(8) . . . . ?
C9 C10 C11 C12 -3.7(12) . . . . ?
C10 C11 C12 C13 1.3(14) . . . . ?
C11 C12 C13 C14 1.5(15) . . . . ?
C12 C13 C14 C9 -1.9(15) . . . . ?
C8 C9 C14 C13 177.1(9) . . . . ?
C10 C9 C14 C13 -0.6(13) . . . . ?
C26 N3 C15 C16 -0.8(11) . . . . ?
Cu1 N3 C15 C16 -170.9(6) . . . . ?
N3 C15 C16 C17 1.0(13) . . . . ?
C15 C16 C17 C18 -1.1(13) . . . . ?
C16 C17 C18 C26 1.1(12) . . . . ?
C16 C17 C18 C19 -179.2(9) . . . . ?
C26 C18 C19 C20 -1.4(14) . . . . ?
C17 C18 C19 C20 179.0(8) . . . . ?
C18 C19 C20 C21 2.3(15) . . . . ?
C19 C20 C21 C22 177.6(9) . . . . ?
C19 C20 C21 C25 -2.4(13) . . . . ?
C20 C21 C22 C23 -179.4(9) . . . . ?
C25 C21 C22 C23 0.6(12) . . . . ?
C21 C22 C23 C24 0.9(13) . . . . ?
C25 N4 C24 C23 -1.6(11) . . . . ?
Cu1 N4 C24 C23 174.6(6) . . . . ?
C22 C23 C24 N4 -0.5(13) . . . . ?
C24 N4 C25 C21 3.2(10) . . . . ?
Cu1 N4 C25 C21 -173.8(6) . . . . ?
C24 N4 C25 C26 179.0(6) . . . . ?
Cu1 N4 C25 C26 2.0(7) . . . . ?
C22 C21 C25 N4 -2.8(11) . . . . ?
C20 C21 C25 N4 177.2(8) . . . . ?
C22 C21 C25 C26 -178.5(7) . . . . ?
C20 C21 C25 C26 1.6(11) . . . . ?
C15 N3 C26 C18 0.8(11) . . . . ?
Cu1 N3 C26 C18 171.8(6) . . . . ?
C15 N3 C26 C25 179.7(6) . . . . ?
Cu1 N3 C26 C25 -9.4(9) . . . . ?
C17 C18 C26 N3 -1.0(12) . . . . ?
C19 C18 C26 N3 179.4(8) . . . . ?
C17 C18 C26 C25 -179.8(6) . . . . ?
C19 C18 C26 C25 0.5(12) . . . . ?
N4 C25 C26 N3 4.4(10) . . . . ?
C21 C25 C26 N3 -179.6(7) . . . . ?
N4 C25 C26 C18 -176.7(7) . . . . ?
C21 C25 C26 C18 -0.7(10) . . . . ?

_refine_diff_density_max         0.655
_refine_diff_density_min         -0.373
_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_1bpy_2MeOH
_database_code_depnum_ccdc_archive 'CCDC 1520853'
_audit_update_record             
;
2016-12-05 deposited with the CCDC.
2017-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H14 Cu N3 O2, C H4 O'
_chemical_formula_sum            'C20 H18 Cu N3 O3'
_chemical_formula_weight         411.91

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

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

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

_cell_length_a                   11.3899(3)
_cell_length_b                   7.9499(2)
_cell_length_c                   20.1358(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.746(2)
_cell_angle_gamma                90
_cell_volume                     1796.95(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6887
_cell_measurement_theta_min      4.4390
_cell_measurement_theta_max      32.0930

_exptl_crystal_description       prism
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.523
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    1.242
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.73530
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35.
Empirical absorption correction using 
spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17601
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         4.107
_diffrn_reflns_theta_max         28.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             4750
_reflns_number_gt                4312
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'CrysAlisPro, Oxford Diffraction Ltd.,Version 1.171.37.35'
_computing_cell_refinement       
'CrysAlisPro, Oxford Diffraction Ltd.,Version 1.171.37.35'
_computing_data_reduction        
'CrysAlisPro, Oxford Diffraction Ltd.,Version 1.171.37.35'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY 3.8. (CCDC, 2016)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0514P)²+1.1931P] 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         4750
_refine_ls_number_parameters     248
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0425
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.0985
_refine_ls_wR_factor_gt          0.0956
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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 0.96540(2) 0.20466(3) 0.99957(2) 0.01880(8) Uani 1 1 d . . . . .
O1 O 0.97279(11) 0.34278(17) 1.07942(7) 0.0216(3) Uani 1 1 d . . . . .
O2 O 0.98074(11) 0.06087(17) 0.92595(7) 0.0218(3) Uani 1 1 d . . . . .
N2 N 1.15488(14) 0.4186(2) 1.05228(8) 0.0229(3) Uani 1 1 d . . . . .
N1 N 1.11640(13) 0.31209(19) 0.99814(8) 0.0200(3) Uani 1 1 d . . . . .
C17 C 0.56137(14) 0.0305(2) 0.99921(9) 0.0193(3) Uani 1 1 d . . . . .
C10 C 1.05739(16) 0.0785(2) 0.88404(9) 0.0208(3) Uani 1 1 d . . . . .
N3 N 0.79417(13) 0.1423(2) 0.99680(8) 0.0201(3) Uani 1 1 d . . . . .
C8 C 1.18185(16) 0.3001(2) 0.95198(10) 0.0225(4) Uani 1 1 d . . . . .
H8 H 1.2515 0.3677 0.9562 0.027 Uiso 1 1 calc R U . . .
C9 C 1.15568(16) 0.1902(2) 0.89425(10) 0.0223(4) Uani 1 1 d . . . . .
C3 C 1.01918(17) 0.5158(3) 1.20038(10) 0.0266(4) Uani 1 1 d . . . . .
H3 H 0.9513 0.4446 1.1917 0.032 Uiso 1 1 calc R U . . .
C16 C 0.61997(16) 0.1387(3) 1.04861(10) 0.0262(4) Uani 1 1 d . . . . .
H16 H 0.5810 0.1766 1.0840 0.031 Uiso 1 1 calc R U . . .
C7 C 1.19546(18) 0.6326(3) 1.16717(10) 0.0272(4) Uani 1 1 d . . . . .
H7 H 1.2486 0.6415 1.1357 0.033 Uiso 1 1 calc R U . . .
C19 C 0.73787(16) 0.0406(2) 0.94851(10) 0.0227(4) Uani 1 1 d . . . . .
H19 H 0.7783 0.0065 0.9132 0.027 Uiso 1 1 calc R U . . .
C18 C 0.62310(15) -0.0163(2) 0.94829(10) 0.0229(4) Uani 1 1 d . . . . .
H18 H 0.5862 -0.0880 0.9131 0.028 Uiso 1 1 calc R U . . .
C14 C 1.23490(19) 0.1936(3) 0.84730(11) 0.0300(4) Uani 1 1 d . . . . .
H14 H 1.3006 0.2689 0.8544 0.036 Uiso 1 1 calc R U . . .
C1 C 1.07270(15) 0.4226(2) 1.09139(9) 0.0199(3) Uani 1 1 d . . . . .
C2 C 1.09683(15) 0.5255(2) 1.15385(9) 0.0216(3) Uani 1 1 d . . . . .
C12 C 1.1223(2) -0.0191(3) 0.78139(11) 0.0331(4) Uani 1 1 d . . . . .
H12 H 1.1109 -0.0913 0.7432 0.040 Uiso 1 1 calc R U . . .
C11 C 1.04307(17) -0.0241(3) 0.82599(10) 0.0258(4) Uani 1 1 d . . . . .
H11 H 0.9770 -0.0986 0.8175 0.031 Uiso 1 1 calc R U . . .
C13 C 1.2194(2) 0.0912(3) 0.79167(11) 0.0360(5) Uani 1 1 d . . . . .
H13 H 1.2737 0.0951 0.7607 0.043 Uiso 1 1 calc R U . . .
C6 C 1.2157(2) 0.7257(3) 1.22617(12) 0.0341(5) Uani 1 1 d . . . . .
H6 H 1.2831 0.7977 1.2352 0.041 Uiso 1 1 calc R U . . .
C15 C 0.73480(16) 0.1905(2) 1.04585(10) 0.0252(4) Uani 1 1 d . . . . .
H15 H 0.7735 0.2634 1.0801 0.030 Uiso 1 1 calc R U . . .
C5 C 1.1384(2) 0.7142(3) 1.27205(11) 0.0363(5) Uani 1 1 d . . . . .
H5 H 1.1527 0.7784 1.3124 0.044 Uiso 1 1 calc R U . . .
C4 C 1.0405(2) 0.6095(3) 1.25917(11) 0.0343(5) Uani 1 1 d . . . . .
H4 H 0.9876 0.6016 1.2908 0.041 Uiso 1 1 calc R U . . .
O3 O 1.40696(14) 0.4029(2) 1.07705(11) 0.0455(4) Uani 1 1 d D . . . .
H3O H 1.3349(17) 0.422(4) 1.0732(16) 0.055 Uiso 1 1 d D U . . .
C20 C 1.4751(2) 0.5465(3) 1.09047(16) 0.0483(6) Uani 1 1 d . . . . .
H20A H 1.4642 0.5927 1.1341 0.072 Uiso 1 1 calc R U . . .
H20B H 1.4501 0.6300 1.0551 0.072 Uiso 1 1 calc R U . . .
H20C H 1.5592 0.5187 1.0917 0.072 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 O2 1.9032(13) . ?
Cu1 N1 1.9248(15) . ?
Cu1 O1 1.9371(13) . ?
Cu1 N3 2.0040(15) . ?
O1 C1 1.289(2) . ?
O2 C10 1.321(2) . ?
N2 C1 1.322(2) . ?
N2 N1 1.391(2) . ?
N1 C8 1.290(2) . ?
C17 C18 1.389(3) . ?
C17 C16 1.396(3) . ?
C17 C17 1.485(3) 3_657 ?
C10 C11 1.412(3) . ?
C10 C9 1.416(3) . ?
N3 C19 1.341(2) . ?
N3 C15 1.344(2) . ?
C8 C9 1.445(3) . ?
C8 H8 0.9500 . ?
C9 C14 1.413(3) . ?
C3 C4 1.385(3) . ?
C3 C2 1.395(3) . ?
C3 H3 0.9500 . ?
C16 C15 1.381(3) . ?
C16 H16 0.9500 . ?
C7 C6 1.385(3) . ?
C7 C2 1.399(3) . ?
C7 H7 0.9500 . ?
C19 C18 1.383(2) . ?
C19 H19 0.9500 . ?
C18 H18 0.9500 . ?
C14 C13 1.372(3) . ?
C14 H14 0.9500 . ?
C1 C2 1.486(2) . ?
C12 C11 1.378(3) . ?
C12 C13 1.399(3) . ?
C12 H12 0.9500 . ?
C11 H11 0.9500 . ?
C13 H13 0.9500 . ?
C6 C5 1.383(4) . ?
C6 H6 0.9500 . ?
C15 H15 0.9500 . ?
C5 C4 1.381(3) . ?
C5 H5 0.9500 . ?
C4 H4 0.9500 . ?
O3 C20 1.381(3) . ?
O3 H3O 0.826(18) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 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
O2 Cu1 N1 93.14(6) . . ?
O2 Cu1 O1 171.95(5) . . ?
N1 Cu1 O1 81.23(6) . . ?
O2 Cu1 N3 92.69(6) . . ?
N1 Cu1 N3 167.75(7) . . ?
O1 Cu1 N3 93.94(6) . . ?
C1 O1 Cu1 110.30(11) . . ?
C10 O2 Cu1 126.28(12) . . ?
C1 N2 N1 108.71(14) . . ?
C8 N1 N2 117.76(15) . . ?
C8 N1 Cu1 127.23(13) . . ?
N2 N1 Cu1 114.96(11) . . ?
C18 C17 C16 116.78(15) . . ?
C18 C17 C17 121.6(2) . 3_657 ?
C16 C17 C17 121.6(2) . 3_657 ?
O2 C10 C11 118.12(16) . . ?
O2 C10 C9 124.45(17) . . ?
C11 C10 C9 117.39(17) . . ?
C19 N3 C15 117.81(15) . . ?
C19 N3 Cu1 120.86(12) . . ?
C15 N3 Cu1 121.15(12) . . ?
N1 C8 C9 123.98(16) . . ?
N1 C8 H8 118.0 . . ?
C9 C8 H8 118.0 . . ?
C14 C9 C10 119.58(18) . . ?
C14 C9 C8 117.28(17) . . ?
C10 C9 C8 123.12(17) . . ?
C4 C3 C2 120.33(19) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C15 C16 C17 119.78(17) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C6 C7 C2 120.1(2) . . ?
C6 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
N3 C19 C18 122.37(17) . . ?
N3 C19 H19 118.8 . . ?
C18 C19 H19 118.8 . . ?
C19 C18 C17 120.42(17) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C13 C14 C9 121.74(19) . . ?
C13 C14 H14 119.1 . . ?
C9 C14 H14 119.1 . . ?
O1 C1 N2 124.64(16) . . ?
O1 C1 C2 117.37(16) . . ?
N2 C1 C2 117.99(16) . . ?
C3 C2 C7 118.98(18) . . ?
C3 C2 C1 119.37(16) . . ?
C7 C2 C1 121.64(17) . . ?
C11 C12 C13 120.71(19) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C12 C11 C10 121.75(18) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C14 C13 C12 118.82(19) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
C5 C6 C7 120.4(2) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
N3 C15 C16 122.83(17) . . ?
N3 C15 H15 118.6 . . ?
C16 C15 H15 118.6 . . ?
C4 C5 C6 120.0(2) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C4 C3 120.3(2) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C20 O3 H3O 112(2) . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C1 N2 N1 C8 175.78(16) . . . . ?
C1 N2 N1 Cu1 -1.91(18) . . . . ?
Cu1 O2 C10 C11 -169.86(13) . . . . ?
Cu1 O2 C10 C9 12.2(3) . . . . ?
N2 N1 C8 C9 177.61(16) . . . . ?
Cu1 N1 C8 C9 -5.0(3) . . . . ?
O2 C10 C9 C14 177.41(18) . . . . ?
C11 C10 C9 C14 -0.6(3) . . . . ?
O2 C10 C9 C8 -1.0(3) . . . . ?
C11 C10 C9 C8 -178.98(17) . . . . ?
N1 C8 C9 C14 178.80(18) . . . . ?
N1 C8 C9 C10 -2.8(3) . . . . ?
C18 C17 C16 C15 -1.4(3) . . . . ?
C17 C17 C16 C15 179.0(2) 3_657 . . . ?
C15 N3 C19 C18 -0.8(3) . . . . ?
Cu1 N3 C19 C18 174.43(15) . . . . ?
N3 C19 C18 C17 -0.2(3) . . . . ?
C16 C17 C18 C19 1.2(3) . . . . ?
C17 C17 C18 C19 -179.2(2) 3_657 . . . ?
C10 C9 C14 C13 0.0(3) . . . . ?
C8 C9 C14 C13 178.4(2) . . . . ?
Cu1 O1 C1 N2 3.9(2) . . . . ?
Cu1 O1 C1 C2 -175.76(12) . . . . ?
N1 N2 C1 O1 -1.4(2) . . . . ?
N1 N2 C1 C2 178.25(14) . . . . ?
C4 C3 C2 C7 -0.8(3) . . . . ?
C4 C3 C2 C1 179.45(18) . . . . ?
C6 C7 C2 C3 0.7(3) . . . . ?
C6 C7 C2 C1 -179.49(18) . . . . ?
O1 C1 C2 C3 7.7(2) . . . . ?
N2 C1 C2 C3 -171.98(17) . . . . ?
O1 C1 C2 C7 -172.04(17) . . . . ?
N2 C1 C2 C7 8.3(3) . . . . ?
C13 C12 C11 C10 -1.1(3) . . . . ?
O2 C10 C11 C12 -176.94(18) . . . . ?
C9 C10 C11 C12 1.2(3) . . . . ?
C9 C14 C13 C12 0.1(3) . . . . ?
C11 C12 C13 C14 0.5(4) . . . . ?
C2 C7 C6 C5 -0.4(3) . . . . ?
C19 N3 C15 C16 0.6(3) . . . . ?
Cu1 N3 C15 C16 -174.58(16) . . . . ?
C17 C16 C15 N3 0.5(3) . . . . ?
C7 C6 C5 C4 0.1(4) . . . . ?
C6 C5 C4 C3 -0.1(3) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?

_refine_diff_density_max         1.519
_refine_diff_density_min         -0.569
_refine_diff_density_rms         0.076

####################################################################### 
# 
# 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_2a_4MeOH_2H2O
_database_code_depnum_ccdc_archive 'CCDC 1520857'
_audit_update_record             
;
2016-12-05 deposited with the CCDC.
2017-02-10 downloaded from the CCDC.
;

_vrf_PLAT417_2MeOH_cubane_revised 
;
PROBLEM: Short Inter D...A Contact O1ME .. O1W and O1W .. O2ME

RESPONSE: 

The contribution of solvent voids areas 
to smeared electron density 
has been
modelled 300 ?3 as 4MeOH.2H2O on the 
basis of intermolecular hydrogen bonds between 
solvent and complex molecules. 
The non-hydrogen atoms of solvent 
molecules in both structures have 
been refined isotropically. Hydrogen 
atoms of solvent molecules in both 
structures were not found in electron-density 
difference Fourier maps.
;

# end Validation Reply Form 


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C64 H46 Cu4 N8 O18'
_chemical_formula_weight         1469.25

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_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                   25.256(2)
_cell_length_b                   11.1490(5)
_cell_length_c                   25.821(2)
_cell_angle_alpha                90
_cell_angle_beta                 120.069(11)
_cell_angle_gamma                90
_cell_volume                     6292.2(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5679
_cell_measurement_theta_min      4.0771
_cell_measurement_theta_max      32.0368

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_F_000             2984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.16
_exptl_absorpt_coefficient_mu    1.413
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.91764
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44.
Empirical absorption correction using 
spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17702
_diffrn_reflns_av_unetI/netI     0.0815
_diffrn_reflns_av_R_equivalents  0.0498
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         4.085
_diffrn_reflns_theta_max         29.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             8337
_reflns_number_gt                6289
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'CrysAlisPro, Oxford Diffraction Ltd.,Version 1.171.34.44'
_computing_cell_refinement       
'CrysAlisPro, Oxford Diffraction Ltd.,Version 1.171.34.44'
_computing_data_reduction        
'CrysAlisPro, Oxford Diffraction Ltd.,Version 1.171.34.44'
_computing_structure_solution    'SHELXLS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY 3.7. (CCDC, 2015)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0571P)²+121.6043P] 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         8337
_refine_ls_number_parameters     401
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1311
_refine_ls_R_factor_gt           0.1015
_refine_ls_wR_factor_ref         0.2413
_refine_ls_wR_factor_gt          0.2270
_refine_ls_goodness_of_fit_ref   1.150
_refine_ls_restrained_S_all      1.150
_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 0.06576(4) 0.68632(7) 0.24222(4) 0.0213(2) Uani 1 1 d . . . . .
Cu2 Cu -0.04614(4) 0.49405(7) 0.17302(4) 0.0226(2) Uani 1 1 d . . . . .
N11 N 0.0627(3) 0.8578(5) 0.2306(2) 0.0227(11) Uani 1 1 d . . . . .
N12 N 0.1170(3) 0.9162(5) 0.2706(3) 0.0285(13) Uani 1 1 d . . . . .
N21 N -0.0592(3) 0.3250(6) 0.1707(3) 0.0336(14) Uani 1 1 d . . . . .
N22 N -0.0408(4) 0.2606(6) 0.1360(4) 0.0450(19) Uani 1 1 d . . . . .
O11 O 0.1481(2) 0.7222(4) 0.3036(2) 0.0280(10) Uani 1 1 d . . . . .
O12 O -0.0200(2) 0.6661(4) 0.1828(2) 0.0224(9) Uani 1 1 d . . . . .
O13 O -0.1288(2) 0.5952(4) 0.0982(2) 0.0281(10) Uani 1 1 d . . . . .
O21 O -0.0206(2) 0.4533(4) 0.1162(2) 0.0279(10) Uani 1 1 d . . . . .
O22 O 0.0674(2) 0.5156(4) 0.2638(2) 0.0254(10) Uani 1 1 d . . . . .
O23 O 0.1068(2) 0.5898(4) 0.1926(2) 0.0319(11) Uani 1 1 d . . . . .
C11 C 0.1577(3) 0.8375(6) 0.3061(3) 0.0253(14) Uani 1 1 d . . . . .
C12 C 0.2188(3) 0.8803(7) 0.3531(3) 0.0303(16) Uani 1 1 d . . . . .
C13 C 0.2289(4) 1.0000(8) 0.3713(4) 0.0392(18) Uani 1 1 d . . . . .
H13 H 0.1965 1.0564 0.3523 0.047 Uiso 1 1 calc R U . . .
C14 C 0.2851(4) 1.0373(10) 0.4165(4) 0.051(2) Uani 1 1 d . . . . .
H14 H 0.2912 1.1190 0.4287 0.061 Uiso 1 1 calc R U . . .
C15 C 0.3323(4) 0.9571(10) 0.4441(4) 0.052(3) Uani 1 1 d . . . . .
H15 H 0.3713 0.9827 0.4751 0.063 Uiso 1 1 calc R U . . .
C16 C 0.3224(4) 0.8390(10) 0.4265(4) 0.048(2) Uani 1 1 d . . . . .
H16 H 0.3547 0.7826 0.4461 0.057 Uiso 1 1 calc R U . . .
C17 C 0.2662(3) 0.8011(8) 0.3804(3) 0.0363(17) Uani 1 1 d . . . . .
H17 H 0.2606 0.7198 0.3678 0.044 Uiso 1 1 calc R U . . .
C18 C 0.0180(3) 0.9200(6) 0.1922(3) 0.0251(14) Uani 1 1 d . . . . .
H18 H 0.0233 1.0044 0.1928 0.030 Uiso 1 1 calc R U . . .
C19 C -0.0406(3) 0.8703(6) 0.1475(3) 0.0212(12) Uani 1 1 d . . . . .
C21 C -0.0233(4) 0.3396(6) 0.1089(3) 0.0315(16) Uani 1 1 d . . . . .
C22 C -0.0027(4) 0.2864(7) 0.0685(4) 0.0384(19) Uani 1 1 d . . . . .
C23 C 0.0214(5) 0.1731(9) 0.0767(5) 0.055(3) Uani 1 1 d . . . . .
H23 H 0.0263 0.1267 0.1097 0.065 Uiso 1 1 calc R U . . .
C24 C 0.0387(5) 0.1248(9) 0.0380(5) 0.062(3) Uani 1 1 d . . . . .
H24 H 0.0562 0.0469 0.0447 0.075 Uiso 1 1 calc R U . . .
C25 C 0.0298(5) 0.1935(10) -0.0116(5) 0.062(3) Uani 1 1 d . . . . .
H25 H 0.0394 0.1606 -0.0398 0.074 Uiso 1 1 calc R U . . .
C26 C 0.0075(4) 0.3071(10) -0.0187(4) 0.048(2) Uani 1 1 d . . . . .
H26 H 0.0026 0.3540 -0.0516 0.057 Uiso 1 1 calc R U . . .
C27 C -0.0080(4) 0.3548(8) 0.0212(4) 0.0383(18) Uani 1 1 d . . . . .
H27 H -0.0224 0.4351 0.0163 0.046 Uiso 1 1 calc R U . . .
C28 C -0.0820(4) 0.2621(6) 0.1967(4) 0.0354(17) Uani 1 1 d . . . . .
H28 H -0.0845 0.1777 0.1909 0.043 Uiso 1 1 calc R U . . .
C29 C 0.1043(3) 0.3115(6) 0.2657(3) 0.0300(15) Uani 1 1 d . . . . .
C110 C -0.0570(3) 0.7496(6) 0.1431(3) 0.0208(12) Uani 1 1 d . . . . .
C111 C -0.1153(3) 0.7152(6) 0.0981(3) 0.0248(13) Uani 1 1 d . . . . .
C112 C -0.1558(3) 0.7968(6) 0.0577(3) 0.0288(15) Uani 1 1 d . . . . .
H112 H -0.1948 0.7706 0.0269 0.035 Uiso 1 1 calc R U . . .
C113 C -0.1400(3) 0.9173(7) 0.0617(3) 0.0302(15) Uani 1 1 d . . . . .
H113 H -0.1683 0.9740 0.0343 0.036 Uiso 1 1 calc R U . . .
C114 C -0.0832(3) 0.9535(6) 0.1054(3) 0.0263(14) Uani 1 1 d . . . . .
H114 H -0.0721 1.0355 0.1078 0.032 Uiso 1 1 calc R U . . .
C115 C -0.1915(3) 0.5601(7) 0.0704(4) 0.0359(17) Uani 1 1 d . . . . .
H11A H -0.2134 0.6139 0.0833 0.054 Uiso 1 1 calc R U . . .
H11B H -0.1942 0.4776 0.0821 0.054 Uiso 1 1 calc R U . . .
H11C H -0.2100 0.5645 0.0269 0.054 Uiso 1 1 calc R U . . .
C210 C 0.0958(3) 0.4354(6) 0.2481(3) 0.0213(13) Uani 1 1 d . . . . .
C211 C 0.1187(3) 0.4711(6) 0.2101(3) 0.0291(15) Uani 1 1 d . . . . .
C212 C 0.1490(4) 0.3947(7) 0.1921(4) 0.0388(18) Uani 1 1 d . . . . .
H212 H 0.1653 0.4229 0.1682 0.047 Uiso 1 1 calc R U . . .
C213 C 0.1553(4) 0.2740(8) 0.2097(4) 0.041(2) Uani 1 1 d . . . . .
H213 H 0.1753 0.2198 0.1967 0.049 Uiso 1 1 calc R U . . .
C215 C 0.1385(6) 0.6445(9) 0.1666(6) 0.067(3) Uani 1 1 d . . . . .
H21A H 0.1826 0.6420 0.1950 0.101 Uiso 1 1 calc R U . . .
H21B H 0.1252 0.7281 0.1567 0.101 Uiso 1 1 calc R U . . .
H21C H 0.1296 0.6012 0.1301 0.101 Uiso 1 1 calc R U . . .
C214 C 0.1332(4) 0.2328(7) 0.2453(4) 0.0369(18) Uani 1 1 d . . . . .
O1ME O -0.1723(12) 1.215(2) 0.0306(12) 0.258(10) Uiso 1 1 d . . . . .
O2ME O 0.2754(14) 0.428(3) 0.3462(15) 0.313(14) Uiso 1 1 d . . . . .
C1ME C -0.262(2) 0.309(4) 0.023(2) 0.274(19) Uiso 1 1 d . . . . .
O1W O -0.313(2) 0.381(5) 0.063(2) 0.48(3) Uiso 1 1 d . . . . .
C2ME C 0.196(3) -0.020(6) 0.191(3) 0.37(3) 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 O11 1.922(5) . ?
Cu1 N11 1.930(5) . ?
Cu1 O12 1.940(5) . ?
Cu1 O22 1.979(5) . ?
Cu1 O23 2.281(5) . ?
Cu2 N21 1.909(7) . ?
Cu2 O21 1.931(5) . ?
Cu2 O22 1.970(4) 2 ?
Cu2 O12 2.004(4) . ?
Cu2 O13 2.306(5) . ?
N11 C18 1.271(9) . ?
N11 N12 1.396(8) . ?
N12 C11 1.312(9) . ?
N21 C28 1.290(9) . ?
N21 N22 1.399(8) . ?
N22 C21 1.330(10) . ?
O11 C11 1.304(8) . ?
O12 C110 1.353(8) . ?
O13 C111 1.380(8) . ?
O13 C115 1.428(9) . ?
O21 C21 1.278(8) . ?
O22 C210 1.330(8) . ?
O22 Cu2 1.970(4) 2 ?
O23 C211 1.382(8) . ?
O23 C215 1.415(9) . ?
C11 C12 1.485(10) . ?
C12 C17 1.365(11) . ?
C12 C13 1.396(12) . ?
C13 C14 1.375(12) . ?
C13 H13 0.9500 . ?
C14 C15 1.370(15) . ?
C14 H14 0.9500 . ?
C15 C16 1.375(15) . ?
C15 H15 0.9500 . ?
C16 C17 1.384(11) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
C18 C19 1.455(9) . ?
C18 H18 0.9500 . ?
C19 C110 1.396(8) . ?
C19 C114 1.424(9) . ?
C21 C22 1.502(10) . ?
C22 C23 1.371(13) . ?
C22 C27 1.389(12) . ?
C23 C24 1.385(13) . ?
C23 H23 0.9500 . ?
C24 C25 1.410(16) . ?
C24 H24 0.9500 . ?
C25 C26 1.361(15) . ?
C25 H25 0.9500 . ?
C26 C27 1.380(11) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C29 1.451(10) 2 ?
C28 H28 0.9500 . ?
C29 C214 1.402(10) . ?
C29 C210 1.437(9) . ?
C29 C28 1.451(10) 2 ?
C110 C111 1.397(9) . ?
C111 C112 1.376(10) . ?
C112 C113 1.391(10) . ?
C112 H112 0.9500 . ?
C113 C114 1.368(10) . ?
C113 H113 0.9500 . ?
C114 H114 0.9500 . ?
C115 H11A 0.9800 . ?
C115 H11B 0.9800 . ?
C115 H11C 0.9800 . ?
C210 C211 1.424(9) . ?
C211 C212 1.371(10) . ?
C212 C213 1.403(11) . ?
C212 H212 0.9500 . ?
C213 C214 1.372(11) . ?
C213 H213 0.9500 . ?
C215 H21A 0.9800 . ?
C215 H21B 0.9800 . ?
C215 H21C 0.9800 . ?
O1ME C1ME 1.56(4) 7_465 ?
O2ME C2ME 1.57(6) 4 ?
C1ME O1ME 1.56(4) 7_465 ?
C2ME O2ME 1.57(6) 4_545 ?

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
O11 Cu1 N11 82.2(2) . . ?
O11 Cu1 O12 173.7(2) . . ?
N11 Cu1 O12 92.9(2) . . ?
O11 Cu1 O22 96.1(2) . . ?
N11 Cu1 O22 172.0(2) . . ?
O12 Cu1 O22 88.19(19) . . ?
O11 Cu1 O23 87.3(2) . . ?
N11 Cu1 O23 111.9(2) . . ?
O12 Cu1 O23 98.2(2) . . ?
O22 Cu1 O23 75.72(18) . . ?
N21 Cu2 O21 82.1(2) . . ?
N21 Cu2 O22 91.8(2) . 2 ?
O21 Cu2 O22 172.5(2) . 2 ?
N21 Cu2 O12 172.0(2) . . ?
O21 Cu2 O12 96.2(2) . . ?
O22 Cu2 O12 89.30(19) 2 . ?
N21 Cu2 O13 112.8(2) . . ?
O21 Cu2 O13 89.2(2) . . ?
O22 Cu2 O13 97.25(19) 2 . ?
O12 Cu2 O13 74.95(18) . . ?
C18 N11 N12 118.8(6) . . ?
C18 N11 Cu1 127.7(5) . . ?
N12 N11 Cu1 113.5(4) . . ?
C11 N12 N11 109.9(6) . . ?
C28 N21 N22 115.7(6) . . ?
C28 N21 Cu2 129.5(5) . . ?
N22 N21 Cu2 114.8(5) . . ?
C21 N22 N21 107.6(6) . . ?
C11 O11 Cu1 110.1(4) . . ?
C110 O12 Cu1 126.4(4) . . ?
C110 O12 Cu2 120.2(4) . . ?
Cu1 O12 Cu2 112.2(2) . . ?
C111 O13 C115 118.5(6) . . ?
C111 O13 Cu2 110.8(4) . . ?
C115 O13 Cu2 126.6(4) . . ?
C21 O21 Cu2 109.3(4) . . ?
C210 O22 Cu2 125.7(4) . 2 ?
C210 O22 Cu1 119.9(4) . . ?
Cu2 O22 Cu1 112.0(2) 2 . ?
C211 O23 C215 119.0(6) . . ?
C211 O23 Cu1 110.7(4) . . ?
C215 O23 Cu1 126.0(5) . . ?
O11 C11 N12 124.3(6) . . ?
O11 C11 C12 116.6(6) . . ?
N12 C11 C12 119.1(6) . . ?
C17 C12 C13 118.7(7) . . ?
C17 C12 C11 119.9(7) . . ?
C13 C12 C11 121.4(7) . . ?
C14 C13 C12 120.8(9) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C15 C14 C13 120.2(9) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 119.2(8) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C15 C16 C17 121.0(9) . . ?
C15 C16 H16 119.5 . . ?
C17 C16 H16 119.5 . . ?
C12 C17 C16 120.2(9) . . ?
C12 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
N11 C18 C19 124.3(6) . . ?
N11 C18 H18 117.8 . . ?
C19 C18 H18 117.8 . . ?
C110 C19 C114 119.0(6) . . ?
C110 C19 C18 125.0(6) . . ?
C114 C19 C18 116.0(6) . . ?
O21 C21 N22 126.0(6) . . ?
O21 C21 C22 118.8(6) . . ?
N22 C21 C22 115.2(6) . . ?
C23 C22 C27 118.8(8) . . ?
C23 C22 C21 122.5(8) . . ?
C27 C22 C21 118.7(7) . . ?
C22 C23 C24 121.5(10) . . ?
C22 C23 H23 119.3 . . ?
C24 C23 H23 119.3 . . ?
C23 C24 C25 118.7(10) . . ?
C23 C24 H24 120.6 . . ?
C25 C24 H24 120.6 . . ?
C26 C25 C24 119.7(9) . . ?
C26 C25 H25 120.1 . . ?
C24 C25 H25 120.1 . . ?
C25 C26 C27 120.7(9) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 H26 119.6 . . ?
C26 C27 C22 120.4(8) . . ?
C26 C27 H27 119.8 . . ?
C22 C27 H27 119.8 . . ?
N21 C28 C29 124.5(7) . 2 ?
N21 C28 H28 117.8 . . ?
C29 C28 H28 117.8 2 . ?
C214 C29 C210 120.4(6) . . ?
C214 C29 C28 117.6(7) . 2 ?
C210 C29 C28 122.0(6) . 2 ?
O12 C110 C19 122.4(6) . . ?
O12 C110 C111 118.8(6) . . ?
C19 C110 C111 118.6(6) . . ?
C112 C111 O13 123.5(6) . . ?
C112 C111 C110 121.5(6) . . ?
O13 C111 C110 115.0(6) . . ?
C111 C112 C113 120.4(7) . . ?
C111 C112 H112 119.8 . . ?
C113 C112 H112 119.8 . . ?
C114 C113 C112 119.2(7) . . ?
C114 C113 H113 120.4 . . ?
C112 C113 H113 120.4 . . ?
C113 C114 C19 121.2(6) . . ?
C113 C114 H114 119.4 . . ?
C19 C114 H114 119.4 . . ?
O13 C115 H11A 109.5 . . ?
O13 C115 H11B 109.5 . . ?
H11A C115 H11B 109.5 . . ?
O13 C115 H11C 109.5 . . ?
H11A C115 H11C 109.5 . . ?
H11B C115 H11C 109.5 . . ?
O22 C210 C211 119.4(6) . . ?
O22 C210 C29 124.6(6) . . ?
C211 C210 C29 116.0(6) . . ?
C212 C211 O23 123.4(7) . . ?
C212 C211 C210 123.3(7) . . ?
O23 C211 C210 113.3(6) . . ?
C211 C212 C213 118.6(7) . . ?
C211 C212 H212 120.7 . . ?
C213 C212 H212 120.7 . . ?
C214 C213 C212 121.2(7) . . ?
C214 C213 H213 119.4 . . ?
C212 C213 H213 119.4 . . ?
O23 C215 H21A 109.5 . . ?
O23 C215 H21B 109.5 . . ?
H21A C215 H21B 109.5 . . ?
O23 C215 H21C 109.5 . . ?
H21A C215 H21C 109.5 . . ?
H21B C215 H21C 109.5 . . ?
C213 C214 C29 120.4(7) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C18 N11 N12 C11 -179.3(6) . . . . ?
Cu1 N11 N12 C11 1.4(7) . . . . ?
C28 N21 N22 C21 175.0(8) . . . . ?
Cu2 N21 N22 C21 -5.4(9) . . . . ?
Cu1 O11 C11 N12 -1.1(8) . . . . ?
Cu1 O11 C11 C12 177.7(5) . . . . ?
N11 N12 C11 O11 -0.2(9) . . . . ?
N11 N12 C11 C12 -179.0(6) . . . . ?
O11 C11 C12 C17 17.0(9) . . . . ?
N12 C11 C12 C17 -164.0(7) . . . . ?
O11 C11 C12 C13 -161.5(7) . . . . ?
N12 C11 C12 C13 17.4(10) . . . . ?
C17 C12 C13 C14 -1.1(12) . . . . ?
C11 C12 C13 C14 177.5(7) . . . . ?
C12 C13 C14 C15 0.4(13) . . . . ?
C13 C14 C15 C16 -0.6(14) . . . . ?
C14 C15 C16 C17 1.6(13) . . . . ?
C13 C12 C17 C16 2.0(11) . . . . ?
C11 C12 C17 C16 -176.6(7) . . . . ?
C15 C16 C17 C12 -2.3(12) . . . . ?
N12 N11 C18 C19 179.1(6) . . . . ?
Cu1 N11 C18 C19 -1.7(10) . . . . ?
N11 C18 C19 C110 4.3(11) . . . . ?
N11 C18 C19 C114 -175.2(6) . . . . ?
Cu2 O21 C21 N22 -0.1(11) . . . . ?
Cu2 O21 C21 C22 -177.3(6) . . . . ?
N21 N22 C21 O21 3.7(12) . . . . ?
N21 N22 C21 C22 -179.1(7) . . . . ?
O21 C21 C22 C23 150.7(9) . . . . ?
N22 C21 C22 C23 -26.7(13) . . . . ?
O21 C21 C22 C27 -29.0(12) . . . . ?
N22 C21 C22 C27 153.6(8) . . . . ?
C27 C22 C23 C24 -1.9(15) . . . . ?
C21 C22 C23 C24 178.3(9) . . . . ?
C22 C23 C24 C25 -1.4(16) . . . . ?
C23 C24 C25 C26 3.2(16) . . . . ?
C24 C25 C26 C27 -1.6(15) . . . . ?
C25 C26 C27 C22 -1.8(14) . . . . ?
C23 C22 C27 C26 3.6(13) . . . . ?
C21 C22 C27 C26 -176.7(8) . . . . ?
N22 N21 C28 C29 -179.5(8) . . . 2 ?
Cu2 N21 C28 C29 1.0(13) . . . 2 ?
Cu1 O12 C110 C19 -12.5(9) . . . . ?
Cu2 O12 C110 C19 -179.1(5) . . . . ?
Cu1 O12 C110 C111 171.4(4) . . . . ?
Cu2 O12 C110 C111 4.8(8) . . . . ?
C114 C19 C110 O12 -177.3(6) . . . . ?
C18 C19 C110 O12 3.2(10) . . . . ?
C114 C19 C110 C111 -1.2(9) . . . . ?
C18 C19 C110 C111 179.3(6) . . . . ?
C115 O13 C111 C112 -22.2(10) . . . . ?
Cu2 O13 C111 C112 178.9(5) . . . . ?
C115 O13 C111 C110 157.0(6) . . . . ?
Cu2 O13 C111 C110 -1.9(7) . . . . ?
O12 C110 C111 C112 177.7(6) . . . . ?
C19 C110 C111 C112 1.5(10) . . . . ?
O12 C110 C111 O13 -1.5(9) . . . . ?
C19 C110 C111 O13 -177.7(6) . . . . ?
O13 C111 C112 C113 177.5(7) . . . . ?
C110 C111 C112 C113 -1.6(11) . . . . ?
C111 C112 C113 C114 1.4(11) . . . . ?
C112 C113 C114 C19 -1.1(11) . . . . ?
C110 C19 C114 C113 1.0(10) . . . . ?
C18 C19 C114 C113 -179.4(6) . . . . ?
Cu2 O22 C210 C211 -167.9(5) 2 . . . ?
Cu1 O22 C210 C211 -7.0(8) . . . . ?
Cu2 O22 C210 C29 13.6(9) 2 . . . ?
Cu1 O22 C210 C29 174.4(5) . . . . ?
C214 C29 C210 O22 178.0(7) . . . . ?
C28 C29 C210 O22 0.0(11) 2 . . . ?
C214 C29 C210 C211 -0.6(11) . . . . ?
C28 C29 C210 C211 -178.7(7) 2 . . . ?
C215 O23 C211 C212 -15.2(12) . . . . ?
Cu1 O23 C211 C212 -173.4(7) . . . . ?
C215 O23 C211 C210 165.7(8) . . . . ?
Cu1 O23 C211 C210 7.5(7) . . . . ?
O22 C210 C211 C212 179.5(7) . . . . ?
C29 C210 C211 C212 -1.9(11) . . . . ?
O22 C210 C211 O23 -1.4(9) . . . . ?
C29 C210 C211 O23 177.3(6) . . . . ?
O23 C211 C212 C213 -176.2(8) . . . . ?
C210 C211 C212 C213 2.9(13) . . . . ?
C211 C212 C213 C214 -1.5(14) . . . . ?
C212 C213 C214 C29 -0.9(14) . . . . ?
C210 C29 C214 C213 2.0(13) . . . . ?
C28 C29 C214 C213 -179.9(8) 2 . . . ?

_refine_diff_density_max         1.560
_refine_diff_density_min         -1.064
_refine_diff_density_rms         0.158

####################################################################### 
# 
# 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_2bpy
_database_code_depnum_ccdc_archive 'CCDC 1520854'
_audit_update_record             
;
2016-12-05 deposited with the CCDC.
2017-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H32 Cu2 N6 O6'
_chemical_formula_sum            'C40 H32 Cu2 N6 O6'
_chemical_formula_weight         819.79

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

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

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

_cell_length_a                   16.5056(3)
_cell_length_b                   8.50240(19)
_cell_length_c                   24.0812(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.3660(16)
_cell_angle_gamma                90
_cell_volume                     3373.66(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4638
_cell_measurement_theta_min      4.2720
_cell_measurement_theta_max      30.3560

_exptl_crystal_description       prism
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_F_000             1680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    1.322
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.97733
_exptl_absorpt_correction_T_max  1.00000

_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20138
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_av_R_equivalents  0.0416
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         4.194
_diffrn_reflns_theta_max         29.993
_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             4894
_reflns_number_gt                3769
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 
;

_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY 3.8. (CCDC, 2016)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0455P)²+1.7021P] 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         4894
_refine_ls_number_parameters     245
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0611
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.0991
_refine_ls_wR_factor_gt          0.0903
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.013
_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 0.23955(2) 0.36470(3) 0.66575(2) 0.03093(9) Uani 1 1 d . . . . .
N1 N 0.32446(10) 0.35410(19) 0.72381(7) 0.0286(3) Uani 1 1 d . . . . .
N2 N 0.31021(10) 0.4418(2) 0.77131(7) 0.0330(4) Uani 1 1 d . . . . .
N3 N 0.14836(10) 0.4010(2) 0.60733(7) 0.0327(4) Uani 1 1 d . . . . .
O1 O 0.19194(9) 0.49863(18) 0.71882(6) 0.0348(3) Uani 1 1 d . . . . .
O2 O 0.29521(8) 0.23934(18) 0.61647(6) 0.0364(3) Uani 1 1 d . . . . .
O3 O 0.33848(9) 0.05047(19) 0.54000(6) 0.0367(3) Uani 1 1 d . . . . .
C1 C 0.24009(12) 0.5153(2) 0.76292(8) 0.0292(4) Uani 1 1 d . . . . .
C2 C 0.21484(12) 0.6277(2) 0.80580(8) 0.0304(4) Uani 1 1 d . . . . .
C3 C 0.14177(14) 0.7073(3) 0.79712(10) 0.0385(5) Uani 1 1 d . . . . .
H3 H 0.1088 0.6869 0.7653 0.046 Uiso 1 1 calc R U . . .
C4 C 0.11759(15) 0.8166(3) 0.83520(11) 0.0452(6) Uani 1 1 d . . . . .
H4 H 0.0685 0.8693 0.8289 0.054 Uiso 1 1 calc R U . . .
C5 C 0.16585(16) 0.8477(3) 0.88243(11) 0.0453(6) Uani 1 1 d . . . . .
H5 H 0.1496 0.9214 0.9081 0.054 Uiso 1 1 calc R U . . .
C6 C 0.23840(15) 0.7689(3) 0.89154(10) 0.0432(5) Uani 1 1 d . . . . .
H6 H 0.2711 0.7898 0.9235 0.052 Uiso 1 1 calc R U . . .
C7 C 0.26303(14) 0.6595(3) 0.85387(10) 0.0375(5) Uani 1 1 d . . . . .
H7 H 0.3120 0.6067 0.8606 0.045 Uiso 1 1 calc R U . . .
C8 C 0.39267(12) 0.2802(2) 0.72214(9) 0.0318(4) Uani 1 1 d . . . . .
H8 H 0.4293 0.2883 0.7528 0.038 Uiso 1 1 calc R U . . .
C9 C 0.41553(12) 0.1865(2) 0.67613(9) 0.0300(4) Uani 1 1 d . . . . .
C10 C 0.36498(12) 0.1682(2) 0.62694(8) 0.0289(4) Uani 1 1 d . . . . .
C11 C 0.39168(12) 0.0636(2) 0.58568(8) 0.0303(4) Uani 1 1 d . . . . .
C12 C 0.46425(13) -0.0157(3) 0.59282(9) 0.0368(5) Uani 1 1 d . . . . .
H12 H 0.4801 -0.0844 0.5654 0.044 Uiso 1 1 calc R U . . .
C13 C 0.51431(13) 0.0066(3) 0.64114(10) 0.0396(5) Uani 1 1 d . . . . .
H13 H 0.5637 -0.0458 0.6455 0.048 Uiso 1 1 calc R U . . .
C14 C 0.49054(12) 0.1052(3) 0.68170(10) 0.0364(5) Uani 1 1 d . . . . .
H14 H 0.5242 0.1195 0.7137 0.044 Uiso 1 1 calc R U . . .
C15 C 0.35882(16) -0.0552(3) 0.49752(10) 0.0483(6) Uani 1 1 d . . . . .
H15A H 0.4102 -0.0259 0.4839 0.072 Uiso 1 1 calc R U . . .
H15B H 0.3178 -0.0513 0.4676 0.072 Uiso 1 1 calc R U . . .
H15C H 0.3622 -0.1601 0.5123 0.072 Uiso 1 1 calc R U . . .
C16 C 0.14951(15) 0.3376(3) 0.55691(10) 0.0431(6) Uani 1 1 d . . . . .
H16 H 0.1903 0.2659 0.5500 0.052 Uiso 1 1 calc R U . . .
C17 C 0.09283(15) 0.3735(3) 0.51452(10) 0.0461(6) Uani 1 1 d . . . . .
H17 H 0.0962 0.3256 0.4800 0.055 Uiso 1 1 calc R U . . .
C18 C 0.03097(12) 0.4796(2) 0.52248(8) 0.0303(4) Uani 1 1 d . . . . .
C19 C 0.03075(13) 0.5456(3) 0.57533(9) 0.0421(6) Uani 1 1 d . . . . .
H19 H -0.0091 0.6180 0.5834 0.051 Uiso 1 1 calc R U . . .
C20 C 0.08897(13) 0.5045(3) 0.61562(9) 0.0427(6) Uani 1 1 d . . . . .
H20 H 0.0872 0.5508 0.6505 0.051 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 O2 1.8752(15) . ?
Cu1 O1 1.9144(15) . ?
Cu1 N1 1.9227(16) . ?
Cu1 N3 2.0228(17) . ?
N1 C8 1.292(3) . ?
N1 N2 1.397(2) . ?
N2 C1 1.320(3) . ?
N3 C16 1.330(3) . ?
N3 C20 1.341(3) . ?
O1 C1 1.296(2) . ?
O2 C10 1.312(2) . ?
O3 C11 1.371(2) . ?
O3 C15 1.417(3) . ?
C1 C2 1.484(3) . ?
C2 C3 1.388(3) . ?
C2 C7 1.392(3) . ?
C3 C4 1.381(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.377(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.433(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.417(3) . ?
C9 C14 1.417(3) . ?
C10 C11 1.423(3) . ?
C11 C12 1.376(3) . ?
C12 C13 1.400(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.362(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 C17 1.378(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.384(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.391(3) . ?
C18 C18 1.486(4) 5_566 ?
C19 C20 1.370(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?

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
O2 Cu1 O1 174.91(6) . . ?
O2 Cu1 N1 94.03(7) . . ?
O1 Cu1 N1 81.53(7) . . ?
O2 Cu1 N3 91.08(7) . . ?
O1 Cu1 N3 93.19(7) . . ?
N1 Cu1 N3 173.59(7) . . ?
C8 N1 N2 118.29(16) . . ?
C8 N1 Cu1 126.84(14) . . ?
N2 N1 Cu1 114.83(12) . . ?
C1 N2 N1 108.39(16) . . ?
C16 N3 C20 116.88(18) . . ?
C16 N3 Cu1 121.54(14) . . ?
C20 N3 Cu1 121.15(15) . . ?
C1 O1 Cu1 110.86(13) . . ?
C10 O2 Cu1 126.69(13) . . ?
C11 O3 C15 117.61(17) . . ?
O1 C1 N2 124.28(19) . . ?
O1 C1 C2 117.18(18) . . ?
N2 C1 C2 118.53(18) . . ?
C3 C2 C7 118.7(2) . . ?
C3 C2 C1 119.08(19) . . ?
C7 C2 C1 122.24(19) . . ?
C4 C3 C2 120.7(2) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 120.2(2) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 119.6(2) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C7 C6 C5 120.7(2) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C2 120.2(2) . . ?
C6 C7 H7 119.9 . . ?
C2 C7 H7 119.9 . . ?
N1 C8 C9 124.32(18) . . ?
N1 C8 H8 117.8 . . ?
C9 C8 H8 117.8 . . ?
C10 C9 C14 119.6(2) . . ?
C10 C9 C8 122.58(18) . . ?
C14 C9 C8 117.78(18) . . ?
O2 C10 C9 125.27(19) . . ?
O2 C10 C11 117.28(18) . . ?
C9 C10 C11 117.46(18) . . ?
O3 C11 C12 124.9(2) . . ?
O3 C11 C10 113.66(17) . . ?
C12 C11 C10 121.47(19) . . ?
C11 C12 C13 120.3(2) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 119.9(2) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C9 121.3(2) . . ?
C13 C14 H14 119.4 . . ?
C9 C14 H14 119.4 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 C17 122.8(2) . . ?
N3 C16 H16 118.6 . . ?
C17 C16 H16 118.6 . . ?
C16 C17 C18 121.1(2) . . ?
C16 C17 H17 119.5 . . ?
C18 C17 H17 119.5 . . ?
C17 C18 C19 115.55(19) . . ?
C17 C18 C18 122.2(2) . 5_566 ?
C19 C18 C18 122.2(2) . 5_566 ?
C20 C19 C18 120.4(2) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
N3 C20 C19 123.4(2) . . ?
N3 C20 H20 118.3 . . ?
C19 C20 H20 118.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 N2 C1 175.94(18) . . . . ?
Cu1 N1 N2 C1 -1.7(2) . . . . ?
N1 Cu1 O2 C10 4.51(17) . . . . ?
N3 Cu1 O2 C10 -179.36(17) . . . . ?
Cu1 O1 C1 N2 -3.9(3) . . . . ?
Cu1 O1 C1 C2 174.58(13) . . . . ?
N1 N2 C1 O1 3.7(3) . . . . ?
N1 N2 C1 C2 -174.73(16) . . . . ?
O1 C1 C2 C3 0.6(3) . . . . ?
N2 C1 C2 C3 179.14(19) . . . . ?
O1 C1 C2 C7 -177.61(19) . . . . ?
N2 C1 C2 C7 1.0(3) . . . . ?
C7 C2 C3 C4 0.4(3) . . . . ?
C1 C2 C3 C4 -177.8(2) . . . . ?
C2 C3 C4 C5 -0.1(4) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C4 C5 C6 C7 0.0(4) . . . . ?
C5 C6 C7 C2 0.3(4) . . . . ?
C3 C2 C7 C6 -0.5(3) . . . . ?
C1 C2 C7 C6 177.7(2) . . . . ?
N2 N1 C8 C9 -179.75(18) . . . . ?
Cu1 N1 C8 C9 -2.5(3) . . . . ?
N1 C8 C9 C10 1.1(3) . . . . ?
N1 C8 C9 C14 -176.5(2) . . . . ?
Cu1 O2 C10 C9 -6.9(3) . . . . ?
Cu1 O2 C10 C11 172.67(14) . . . . ?
C14 C9 C10 O2 -178.60(19) . . . . ?
C8 C9 C10 O2 3.8(3) . . . . ?
C14 C9 C10 C11 1.8(3) . . . . ?
C8 C9 C10 C11 -175.72(18) . . . . ?
C15 O3 C11 C12 1.5(3) . . . . ?
C15 O3 C11 C10 -177.98(18) . . . . ?
O2 C10 C11 O3 -0.9(3) . . . . ?
C9 C10 C11 O3 178.74(17) . . . . ?
O2 C10 C11 C12 179.68(19) . . . . ?
C9 C10 C11 C12 -0.7(3) . . . . ?
O3 C11 C12 C13 179.86(19) . . . . ?
C10 C11 C12 C13 -0.7(3) . . . . ?
C11 C12 C13 C14 1.1(3) . . . . ?
C12 C13 C14 C9 0.1(3) . . . . ?
C10 C9 C14 C13 -1.6(3) . . . . ?
C8 C9 C14 C13 176.1(2) . . . . ?
C20 N3 C16 C17 -0.4(4) . . . . ?
Cu1 N3 C16 C17 -172.9(2) . . . . ?
N3 C16 C17 C18 0.2(4) . . . . ?
C16 C17 C18 C19 0.1(4) . . . . ?
C16 C17 C18 C18 -180.0(3) . . . 5_566 ?
C17 C18 C19 C20 -0.2(4) . . . . ?
C18 C18 C19 C20 179.9(3) 5_566 . . . ?
C16 N3 C20 C19 0.4(4) . . . . ?
Cu1 N3 C20 C19 172.9(2) . . . . ?
C18 C19 C20 N3 -0.1(4) . . . . ?

_refine_diff_density_max         0.330
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.063

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_3py
_database_code_depnum_ccdc_archive 'CCDC 1520852'
_audit_update_record             
;
2016-12-05 deposited with the CCDC.
2017-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            'C40 H34 Cu2 N6 O6'
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H34 Cu2 N6 O6'
_chemical_formula_sum            'C40 H34 Cu2 N6 O6'
_chemical_formula_weight         821.81

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   13.5763(6)
_cell_length_b                   10.6885(3)
_cell_length_c                   13.9612(7)
_cell_angle_alpha                90
_cell_angle_beta                 116.912(6)
_cell_angle_gamma                90
_cell_volume                     1806.51(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    10354
_cell_measurement_theta_min      5.4220
_cell_measurement_theta_max      71.0290

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_F_000             844
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.31
_exptl_crystal_size_min          0.25
_exptl_absorpt_coefficient_mu    1.929
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.65455
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28.
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37451
_diffrn_reflns_av_unetI/netI     0.0175
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.651
_diffrn_reflns_theta_max         69.998
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3410
_reflns_number_gt                2971
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'CrysAlisPro, Oxford Diffraction Ltd.,Version 1.171.36.28'
_computing_cell_refinement       
'CrysAlisPro, Oxford Diffraction Ltd.,Version 1.171.36.28'
_computing_data_reduction        
'CrysAlisPro, Oxford Diffraction Ltd.,Version 1.171.36.28'
_computing_structure_solution    'SHELXLS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY 3.7. (CCDC, 2015)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0703P)²+0.7575P] 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         3410
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0400
_refine_ls_wR_factor_ref         0.1235
_refine_ls_wR_factor_gt          0.1178
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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 0.97133(3) 0.49423(3) 0.10136(3) 0.05026(16) Uani 1 1 d . . . . .
N1 N 0.99237(16) 0.31781(17) 0.13223(17) 0.0508(4) Uani 1 1 d . . . . .
N2 N 0.89833(16) 0.25418(18) 0.12103(17) 0.0554(5) Uani 1 1 d . . . . .
N3 N 0.94906(16) 0.68031(17) 0.09785(15) 0.0501(4) Uani 1 1 d . . . . .
O1 O 0.82893(14) 0.45525(16) 0.09545(15) 0.0586(4) Uani 1 1 d . . . . .
O2 O 1.11269(15) 0.51073(14) 0.10438(16) 0.0552(4) Uani 1 1 d . . . . .
O3 O 1.49006(15) 0.4474(2) 0.22652(18) 0.0763(5) Uani 1 1 d . . . . .
C1 C 0.8191(2) 0.3353(2) 0.10104(19) 0.0519(5) Uani 1 1 d . . . . .
C2 C 0.7100(2) 0.2857(2) 0.0829(2) 0.0544(5) Uani 1 1 d . . . . .
C3 C 0.6986(2) 0.1650(2) 0.1144(2) 0.0614(6) Uani 1 1 d . . . . .
H3 H 0.7607 0.1151 0.1506 0.074 Uiso 1 1 calc R U . . .
C4 C 0.5956(3) 0.1194(3) 0.0918(2) 0.0739(8) Uani 1 1 d . . . . .
H4 H 0.5882 0.0382 0.1117 0.089 Uiso 1 1 calc R U . . .
C5 C 0.5034(2) 0.1932(3) 0.0402(3) 0.0798(8) Uani 1 1 d . . . . .
H5 H 0.4341 0.1622 0.0261 0.096 Uiso 1 1 calc R U . . .
C6 C 0.5134(2) 0.3125(3) 0.0094(3) 0.0771(9) Uani 1 1 d . . . . .
H6 H 0.4510 0.3622 -0.0257 0.093 Uiso 1 1 calc R U . . .
C7 C 0.6163(2) 0.3591(3) 0.0305(2) 0.0658(7) Uani 1 1 d . . . . .
H7 H 0.6227 0.4400 0.0095 0.079 Uiso 1 1 calc R U . . .
C8 C 1.0829(2) 0.2554(2) 0.1647(2) 0.0543(6) Uani 1 1 d . . . . .
H8 H 1.0814 0.1711 0.1805 0.065 Uiso 1 1 calc R U . . .
C9 C 1.18536(19) 0.3067(2) 0.17808(19) 0.0525(5) Uani 1 1 d . . . . .
C10 C 1.19683(19) 0.4314(2) 0.14824(19) 0.0513(5) Uani 1 1 d . . . . .
C11 C 1.3011(2) 0.4715(2) 0.1651(2) 0.0571(6) Uani 1 1 d . . . . .
H11 H 1.3095 0.5525 0.1456 0.068 Uiso 1 1 calc R U . . .
C12 C 1.3928(2) 0.3935(3) 0.2103(2) 0.0607(6) Uani 1 1 d . . . . .
C13 C 1.3818(2) 0.2703(3) 0.2370(2) 0.0665(7) Uani 1 1 d . . . . .
H13 H 1.4423 0.2167 0.2648 0.080 Uiso 1 1 calc R U . . .
C14 C 1.2796(2) 0.2304(2) 0.2211(2) 0.0621(6) Uani 1 1 d . . . . .
H14 H 1.2724 0.1487 0.2399 0.074 Uiso 1 1 calc R U . . .
C15 C 0.8500(2) 0.7294(2) 0.0733(2) 0.0582(6) Uani 1 1 d . . . . .
H15 H 0.7911 0.6755 0.0587 0.070 Uiso 1 1 calc R U . . .
C16 C 0.8315(2) 0.8556(2) 0.0687(2) 0.0667(7) Uani 1 1 d . . . . .
H16 H 0.7614 0.8864 0.0517 0.080 Uiso 1 1 calc R U . . .
C17 C 0.9173(3) 0.9362(2) 0.0894(3) 0.0705(7) Uani 1 1 d . . . . .
H17 H 0.9066 1.0224 0.0864 0.085 Uiso 1 1 calc R U . . .
C18 C 1.0193(2) 0.8867(2) 0.1147(3) 0.0695(7) Uani 1 1 d . . . . .
H18 H 1.0793 0.9391 0.1298 0.083 Uiso 1 1 calc R U . . .
C19 C 1.0321(2) 0.7595(2) 0.1174(2) 0.0590(6) Uani 1 1 d . . . . .
H19 H 1.1013 0.7269 0.1335 0.071 Uiso 1 1 calc R U . . .
C20 C 1.5902(2) 0.3812(4) 0.2912(3) 0.0858(9) Uani 1 1 d . . . . .
H20A H 1.6521 0.4291 0.2961 0.129 Uiso 1 1 calc R U . . .
H20B H 1.5964 0.3687 0.3618 0.129 Uiso 1 1 calc R U . . .
H20C H 1.5891 0.3016 0.2589 0.129 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 O2 1.9086(18) . ?
Cu1 N1 1.9265(19) . ?
Cu1 O1 1.9425(17) . ?
Cu1 N3 2.0091(19) . ?
N1 C8 1.286(3) . ?
N1 N2 1.392(3) . ?
N2 C1 1.309(3) . ?
N3 C19 1.335(3) . ?
N3 C15 1.336(3) . ?
O1 C1 1.295(3) . ?
O2 C10 1.329(3) . ?
O3 C12 1.362(3) . ?
O3 C20 1.432(3) . ?
C1 C2 1.482(3) . ?
C2 C7 1.388(4) . ?
C2 C3 1.395(3) . ?
C3 C4 1.376(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.372(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.382(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.427(3) . ?
C8 H8 0.9300 . ?
C9 C14 1.403(3) . ?
C9 C10 1.425(3) . ?
C10 C11 1.393(4) . ?
C11 C12 1.390(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.394(4) . ?
C13 C14 1.371(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.368(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.371(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.371(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.369(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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
O2 Cu1 N1 92.27(7) . . ?
O2 Cu1 O1 172.83(7) . . ?
N1 Cu1 O1 81.00(8) . . ?
O2 Cu1 N3 92.74(7) . . ?
N1 Cu1 N3 168.49(9) . . ?
O1 Cu1 N3 94.33(8) . . ?
C8 N1 N2 117.88(19) . . ?
C8 N1 Cu1 127.40(17) . . ?
N2 N1 Cu1 114.69(14) . . ?
C1 N2 N1 108.91(18) . . ?
C19 N3 C15 117.5(2) . . ?
C19 N3 Cu1 121.25(17) . . ?
C15 N3 Cu1 121.20(16) . . ?
C1 O1 Cu1 109.74(15) . . ?
C10 O2 Cu1 126.67(15) . . ?
C12 O3 C20 117.9(3) . . ?
O1 C1 N2 124.8(2) . . ?
O1 C1 C2 117.8(2) . . ?
N2 C1 C2 117.4(2) . . ?
C7 C2 C3 118.8(2) . . ?
C7 C2 C1 119.7(2) . . ?
C3 C2 C1 121.5(2) . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C6 C5 C4 120.1(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 120.1(3) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C6 C7 C2 120.4(3) . . ?
C6 C7 H7 119.8 . . ?
C2 C7 H7 119.8 . . ?
N1 C8 C9 124.5(2) . . ?
N1 C8 H8 117.8 . . ?
C9 C8 H8 117.8 . . ?
C14 C9 C10 118.0(2) . . ?
C14 C9 C8 118.6(2) . . ?
C10 C9 C8 123.4(2) . . ?
O2 C10 C11 118.5(2) . . ?
O2 C10 C9 123.1(2) . . ?
C11 C10 C9 118.4(2) . . ?
C12 C11 C10 121.7(2) . . ?
C12 C11 H11 119.2 . . ?
C10 C11 H11 119.2 . . ?
O3 C12 C11 115.1(3) . . ?
O3 C12 C13 124.5(2) . . ?
C11 C12 C13 120.4(2) . . ?
C14 C13 C12 118.2(2) . . ?
C14 C13 H13 120.9 . . ?
C12 C13 H13 120.9 . . ?
C13 C14 C9 123.3(2) . . ?
C13 C14 H14 118.4 . . ?
C9 C14 H14 118.4 . . ?
N3 C15 C16 122.8(2) . . ?
N3 C15 H15 118.6 . . ?
C16 C15 H15 118.6 . . ?
C15 C16 C17 119.3(3) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C16 C17 C18 118.4(2) . . ?
C16 C17 H17 120.8 . . ?
C18 C17 H17 120.8 . . ?
C19 C18 C17 119.4(3) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
N3 C19 C18 122.7(2) . . ?
N3 C19 H19 118.7 . . ?
C18 C19 H19 118.7 . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C8 N1 N2 C1 172.0(2) . . . . ?
Cu1 N1 N2 C1 -5.8(3) . . . . ?
Cu1 O1 C1 N2 7.8(3) . . . . ?
Cu1 O1 C1 C2 -171.86(17) . . . . ?
N1 N2 C1 O1 -1.5(3) . . . . ?
N1 N2 C1 C2 178.14(19) . . . . ?
O1 C1 C2 C7 19.2(4) . . . . ?
N2 C1 C2 C7 -160.5(2) . . . . ?
O1 C1 C2 C3 -162.9(2) . . . . ?
N2 C1 C2 C3 17.4(4) . . . . ?
C7 C2 C3 C4 1.1(4) . . . . ?
C1 C2 C3 C4 -176.8(2) . . . . ?
C2 C3 C4 C5 -1.3(5) . . . . ?
C3 C4 C5 C6 0.9(5) . . . . ?
C4 C5 C6 C7 -0.2(5) . . . . ?
C5 C6 C7 C2 0.0(5) . . . . ?
C3 C2 C7 C6 -0.4(4) . . . . ?
C1 C2 C7 C6 177.6(3) . . . . ?
N2 N1 C8 C9 178.7(2) . . . . ?
Cu1 N1 C8 C9 -3.8(4) . . . . ?
N1 C8 C9 C14 175.6(2) . . . . ?
N1 C8 C9 C10 -5.4(4) . . . . ?
Cu1 O2 C10 C11 -165.27(18) . . . . ?
Cu1 O2 C10 C9 15.3(3) . . . . ?
C14 C9 C10 O2 178.4(2) . . . . ?
C8 C9 C10 O2 -0.6(4) . . . . ?
C14 C9 C10 C11 -1.1(3) . . . . ?
C8 C9 C10 C11 180.0(2) . . . . ?
O2 C10 C11 C12 -179.8(2) . . . . ?
C9 C10 C11 C12 -0.3(4) . . . . ?
C20 O3 C12 C11 168.2(3) . . . . ?
C20 O3 C12 C13 -11.0(4) . . . . ?
C10 C11 C12 O3 -177.1(2) . . . . ?
C10 C11 C12 C13 2.2(4) . . . . ?
O3 C12 C13 C14 176.7(3) . . . . ?
C11 C12 C13 C14 -2.4(4) . . . . ?
C12 C13 C14 C9 1.0(4) . . . . ?
C10 C9 C14 C13 0.8(4) . . . . ?
C8 C9 C14 C13 179.8(3) . . . . ?
C19 N3 C15 C16 -0.7(4) . . . . ?
Cu1 N3 C15 C16 -179.1(2) . . . . ?
N3 C15 C16 C17 0.3(5) . . . . ?
C15 C16 C17 C18 -0.3(5) . . . . ?
C16 C17 C18 C19 0.6(5) . . . . ?
C15 N3 C19 C18 1.0(4) . . . . ?
Cu1 N3 C19 C18 179.4(2) . . . . ?
C17 C18 C19 N3 -1.0(5) . . . . ?

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
C15 H15 O1 0.93 2.42 2.974(3) 118.6 .
C19 H19 O2 0.93 2.36 2.912(3) 117.5 .

_refine_diff_density_max         0.644
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_2py_3H2O
_database_code_depnum_ccdc_archive 'CCDC 1520851'
_audit_update_record             
;
2016-12-05 deposited with the CCDC.
2017-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C40 H34 Cu2 N6 O6, 2(H2 O), O'
_chemical_formula_sum            'C40 H38 Cu2 N6 O9'
_chemical_formula_weight         873.86

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'
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           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                   12.4200(10)
_cell_length_b                   8.0353(4)
_cell_length_c                   19.6932(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.427(5)
_cell_angle_gamma                90
_cell_volume                     1961.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2932
_cell_measurement_theta_min      4.4240
_cell_measurement_theta_max      32.2050

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_F_000             900
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_exptl_absorpt_coefficient_mu    1.147
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.85095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.33.
Empirical absorption correction using spherical 
harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11860
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         4.232
_diffrn_reflns_theta_max         28.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             5178
_reflns_number_gt                3993
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'CrysAlisPro, Oxford Diffraction Ltd.,Version 1.171.37.33'
_computing_cell_refinement       
'CrysAlisPro, Oxford Diffraction Ltd.,Version 1.171.37.33'
_computing_data_reduction        
'CrysAlisPro, Oxford Diffraction Ltd.,Version 1.171.37.33'
_computing_structure_solution    'SHELXLS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY 3.7. (CCDC, 2015)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0601P)²+0.7741P] 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         5178
_refine_ls_number_parameters     261
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0665
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1235
_refine_ls_wR_factor_gt          0.1143
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.072
_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 0.53733(2) 0.59589(4) 0.57369(2) 0.02182(11) Uani 1 1 d . . . . .
N1 N 0.66865(17) 0.6956(2) 0.54579(10) 0.0229(4) Uani 1 1 d . . . . .
N2 N 0.76031(17) 0.6616(3) 0.58842(11) 0.0243(4) Uani 1 1 d . . . . .
N3 N 0.40544(17) 0.5159(3) 0.61815(10) 0.0227(4) Uani 1 1 d . . . . .
O1 O 0.63233(14) 0.5367(2) 0.65194(9) 0.0264(4) Uani 1 1 d . . . . .
O2 O 0.45591(14) 0.6688(2) 0.49410(9) 0.0259(4) Uani 1 1 d . . . . .
O3 O 0.30020(17) 0.8049(3) 0.42010(10) 0.0389(5) Uani 1 1 d . . . . .
C1 C 0.7304(2) 0.5803(3) 0.64213(13) 0.0226(5) Uani 1 1 d . . . . .
C2 C 0.8128(2) 0.5408(3) 0.69809(13) 0.0234(5) Uani 1 1 d . . . . .
C3 C 0.7830(2) 0.4507(3) 0.75428(15) 0.0296(6) Uani 1 1 d . . . . .
H3 H 0.7118 0.4078 0.7550 0.035 Uiso 1 1 calc R U . . .
C4 C 0.8556(2) 0.4227(4) 0.80912(16) 0.0360(7) Uani 1 1 d . . . . .
H4 H 0.8339 0.3604 0.8470 0.043 Uiso 1 1 calc R U . . .
C5 C 0.9595(2) 0.4845(4) 0.80936(16) 0.0385(7) Uani 1 1 d . . . . .
H5 H 1.0087 0.4677 0.8475 0.046 Uiso 1 1 calc R U . . .
C6 C 0.9908(2) 0.5722(4) 0.75253(18) 0.0391(7) Uani 1 1 d . . . . .
H6 H 1.0624 0.6132 0.7516 0.047 Uiso 1 1 calc R U . . .
C7 C 0.9182(2) 0.5997(3) 0.69752(15) 0.0319(6) Uani 1 1 d . . . . .
H7 H 0.9405 0.6593 0.6591 0.038 Uiso 1 1 calc R U . . .
C8 C 0.6777(2) 0.8010(3) 0.49682(13) 0.0256(5) Uani 1 1 d . . . . .
H8 H 0.7473 0.8443 0.4899 0.031 Uiso 1 1 calc R U . . .
C9 C 0.5893(2) 0.8569(3) 0.45222(13) 0.0266(5) Uani 1 1 d . . . . .
C10 C 0.4832(2) 0.7931(3) 0.45484(13) 0.0254(5) Uani 1 1 d . . . . .
C11 C 0.4007(2) 0.8663(3) 0.41116(14) 0.0312(6) Uani 1 1 d . . . . .
C12 C 0.4247(3) 0.9881(4) 0.36513(14) 0.0399(7) Uani 1 1 d . . . . .
H12 H 0.3690 1.0326 0.3353 0.048 Uiso 1 1 calc R U . . .
C13 C 0.5301(3) 1.0469(4) 0.36183(15) 0.0405(8) Uani 1 1 d . . . . .
H13 H 0.5460 1.1302 0.3297 0.049 Uiso 1 1 calc R U . . .
C14 C 0.6105(3) 0.9842(3) 0.40506(14) 0.0344(6) Uani 1 1 d . . . . .
H14 H 0.6817 1.0267 0.4034 0.041 Uiso 1 1 calc R U . . .
C15 C 0.2159(3) 0.8688(4) 0.3760(2) 0.0541(10) Uani 1 1 d . . . . .
H15A H 0.2327 0.8492 0.3287 0.081 Uiso 1 1 calc R U . . .
H15B H 0.2085 0.9886 0.3837 0.081 Uiso 1 1 calc R U . . .
H15C H 0.1482 0.8128 0.3850 0.081 Uiso 1 1 calc R U . . .
C16 C 0.4162(2) 0.4128(3) 0.67196(13) 0.0256(5) Uani 1 1 d . . . . .
H16 H 0.4867 0.3874 0.6905 0.031 Uiso 1 1 calc R U . . .
C17 C 0.3288(2) 0.3427(3) 0.70112(14) 0.0305(6) Uani 1 1 d . . . . .
H17 H 0.3390 0.2697 0.7389 0.037 Uiso 1 1 calc R U . . .
C18 C 0.2260(2) 0.3803(4) 0.67460(15) 0.0352(7) Uani 1 1 d . . . . .
H18 H 0.1644 0.3337 0.6938 0.042 Uiso 1 1 calc R U . . .
C19 C 0.2146(2) 0.4879(4) 0.61921(16) 0.0365(7) Uani 1 1 d . . . . .
H19 H 0.1450 0.5163 0.6001 0.044 Uiso 1 1 calc R U . . .
C20 C 0.3059(2) 0.5528(3) 0.59250(14) 0.0277(5) Uani 1 1 d . . . . .
H20 H 0.2979 0.6260 0.5547 0.033 Uiso 1 1 calc R U . . .
O1W O 0.9649(2) 0.6548(10) 0.5265(2) 0.168(3) Uani 1 1 d D . . . .
O2W O 1.0874(15) 0.923(2) 0.5174(11) 0.280(9) Uiso 0.5 1 d . . P . .
H11B H 0.958(4) 0.750(8) 0.504(5) 0.336 Uiso 1 1 d D U . . .
H11A H 0.8949 0.6459 0.5455 0.336 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O2 1.9061(18) . ?
Cu1 N1 1.927(2) . ?
Cu1 O1 1.9430(18) . ?
Cu1 N3 2.008(2) . ?
N1 C8 1.293(3) . ?
N1 N2 1.400(3) . ?
N2 C1 1.315(3) . ?
N3 C20 1.341(3) . ?
N3 C16 1.345(3) . ?
O1 C1 1.293(3) . ?
O2 C10 1.320(3) . ?
O3 C11 1.363(4) . ?
O3 C15 1.416(4) . ?
C1 C2 1.492(4) . ?
C2 C3 1.391(4) . ?
C2 C7 1.393(4) . ?
C3 C4 1.383(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.397(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.385(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.436(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.417(4) . ?
C9 C14 1.417(4) . ?
C10 C11 1.426(4) . ?
C11 C12 1.379(4) . ?
C12 C13 1.397(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.369(4) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.379(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.384(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.393(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.380(4) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
O1W H11B 0.886(5) . ?
O1W H11A 0.970(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 N1 93.10(8) . . ?
O2 Cu1 O1 174.01(7) . . ?
N1 Cu1 O1 81.01(8) . . ?
O2 Cu1 N3 92.89(8) . . ?
N1 Cu1 N3 169.69(8) . . ?
O1 Cu1 N3 92.78(8) . . ?
C8 N1 N2 118.1(2) . . ?
C8 N1 Cu1 126.69(19) . . ?
N2 N1 Cu1 114.81(15) . . ?
C1 N2 N1 108.7(2) . . ?
C20 N3 C16 118.6(2) . . ?
C20 N3 Cu1 121.54(18) . . ?
C16 N3 Cu1 119.65(17) . . ?
C1 O1 Cu1 110.36(16) . . ?
C10 O2 Cu1 124.88(17) . . ?
C11 O3 C15 116.0(3) . . ?
O1 C1 N2 124.7(2) . . ?
O1 C1 C2 116.2(2) . . ?
N2 C1 C2 119.0(2) . . ?
C3 C2 C7 118.5(2) . . ?
C3 C2 C1 119.7(2) . . ?
C7 C2 C1 121.7(2) . . ?
C4 C3 C2 120.9(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C4 C3 120.6(3) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 118.9(3) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C7 C6 C5 120.5(3) . . ?
C7 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C6 C7 C2 120.5(3) . . ?
C6 C7 H7 119.8 . . ?
C2 C7 H7 119.8 . . ?
N1 C8 C9 124.3(2) . . ?
N1 C8 H8 117.8 . . ?
C9 C8 H8 117.8 . . ?
C10 C9 C14 119.7(3) . . ?
C10 C9 C8 122.9(2) . . ?
C14 C9 C8 117.5(3) . . ?
O2 C10 C9 124.6(2) . . ?
O2 C10 C11 117.7(2) . . ?
C9 C10 C11 117.7(2) . . ?
O3 C11 C12 125.3(3) . . ?
O3 C11 C10 113.8(2) . . ?
C12 C11 C10 120.9(3) . . ?
C11 C12 C13 120.7(3) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C14 C13 C12 119.8(3) . . ?
C14 C13 H13 120.1 . . ?
C12 C13 H13 120.1 . . ?
C13 C14 C9 121.1(3) . . ?
C13 C14 H14 119.5 . . ?
C9 C14 H14 119.5 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N3 C16 C17 122.4(3) . . ?
N3 C16 H16 118.8 . . ?
C17 C16 H16 118.8 . . ?
C16 C17 C18 119.1(3) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
C17 C18 C19 118.6(3) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 H18 120.7 . . ?
C20 C19 C18 119.1(3) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
N3 C20 C19 122.2(3) . . ?
N3 C20 H20 118.9 . . ?
C19 C20 H20 118.9 . . ?
H11B O1W H11A 101.5(11) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 N2 C1 167.3(2) . . . . ?
Cu1 N1 N2 C1 -6.1(2) . . . . ?
Cu1 O1 C1 N2 3.6(3) . . . . ?
Cu1 O1 C1 C2 -179.41(16) . . . . ?
N1 N2 C1 O1 1.6(3) . . . . ?
N1 N2 C1 C2 -175.35(19) . . . . ?
O1 C1 C2 C3 4.7(3) . . . . ?
N2 C1 C2 C3 -178.1(2) . . . . ?
O1 C1 C2 C7 -171.7(2) . . . . ?
N2 C1 C2 C7 5.5(4) . . . . ?
C7 C2 C3 C4 1.3(4) . . . . ?
C1 C2 C3 C4 -175.3(2) . . . . ?
C2 C3 C4 C5 0.3(4) . . . . ?
C3 C4 C5 C6 -1.6(5) . . . . ?
C4 C5 C6 C7 1.4(5) . . . . ?
C5 C6 C7 C2 0.2(5) . . . . ?
C3 C2 C7 C6 -1.5(4) . . . . ?
C1 C2 C7 C6 175.0(3) . . . . ?
N2 N1 C8 C9 -175.4(2) . . . . ?
Cu1 N1 C8 C9 -2.8(4) . . . . ?
N1 C8 C9 C10 -4.2(4) . . . . ?
N1 C8 C9 C14 174.3(2) . . . . ?
Cu1 O2 C10 C9 20.8(3) . . . . ?
Cu1 O2 C10 C11 -160.43(18) . . . . ?
C14 C9 C10 O2 176.1(2) . . . . ?
C8 C9 C10 O2 -5.4(4) . . . . ?
C14 C9 C10 C11 -2.7(4) . . . . ?
C8 C9 C10 C11 175.8(2) . . . . ?
C15 O3 C11 C12 2.7(4) . . . . ?
C15 O3 C11 C10 -177.5(2) . . . . ?
O2 C10 C11 O3 5.1(3) . . . . ?
C9 C10 C11 O3 -176.0(2) . . . . ?
O2 C10 C11 C12 -175.1(2) . . . . ?
C9 C10 C11 C12 3.8(4) . . . . ?
O3 C11 C12 C13 177.5(3) . . . . ?
C10 C11 C12 C13 -2.2(4) . . . . ?
C11 C12 C13 C14 -0.6(4) . . . . ?
C12 C13 C14 C9 1.7(4) . . . . ?
C10 C9 C14 C13 0.0(4) . . . . ?
C8 C9 C14 C13 -178.5(2) . . . . ?
C20 N3 C16 C17 0.6(4) . . . . ?
Cu1 N3 C16 C17 -174.49(19) . . . . ?
N3 C16 C17 C18 -0.5(4) . . . . ?
C16 C17 C18 C19 0.0(4) . . . . ?
C17 C18 C19 C20 0.3(4) . . . . ?
C16 N3 C20 C19 -0.3(4) . . . . ?
Cu1 N3 C20 C19 174.7(2) . . . . ?
C18 C19 C20 N3 -0.1(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
C16 H16 O1 0.95 2.34 2.911(3) 118.5 .
C20 H20 O2 0.95 2.38 2.920(3) 115.6 .
C16 H16 O1 0.95 2.34 2.911(3) 118.5 .
C20 H20 O2 0.95 2.38 2.920(3) 115.6 .
C16 H16 O1 0.95 2.34 2.911(3) 118.5 .
C20 H20 O2 0.95 2.38 2.920(3) 115.6 .
C16 H16 O1 0.95 2.34 2.911(3) 118.5 .
C20 H20 O2 0.95 2.38 2.920(3) 115.6 .
C16 H16 O1 0.95 2.34 2.911(3) 118.5 .
C20 H20 O2 0.95 2.38 2.920(3) 115.6 .

_refine_diff_density_max         0.956
_refine_diff_density_min         -0.563
_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_3phen
_database_code_depnum_ccdc_archive 'CCDC 1520856'
_audit_update_record             
;
2016-12-05 deposited with the CCDC.
2017-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            'C27 H20 Cu N4 O3'
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H20 Cu N4 O3'
_chemical_formula_sum            'C27 H20 Cu N4 O3'
_chemical_formula_weight         512.01

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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           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                   18.5945(13)
_cell_length_b                   10.8612(5)
_cell_length_c                   11.6265(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.555(7)
_cell_angle_gamma                90
_cell_volume                     2321.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3592
_cell_measurement_theta_min      4.1418
_cell_measurement_theta_max      28.4054

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_F_000             1052
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.21
_exptl_absorpt_coefficient_mu    0.978
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.74057
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9017
_diffrn_reflns_av_unetI/netI     0.0776
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.150
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4558
_reflns_number_gt                2768
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       
'CrysAlisPro, Oxford Diffraction Ltd.,Version 1.171.34.44'
_computing_cell_refinement       
'CrysAlisPro, Oxford Diffraction Ltd.,Version 1.171.34.44'
_computing_data_reduction        
'CrysAlisPro, Oxford Diffraction Ltd.,Version 1.171.34.44'
_computing_structure_solution    'SHELXLS-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY 3.7. (CCDC, 2015)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0419P)²] 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         4558
_refine_ls_number_parameters     327
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1133
_refine_ls_R_factor_gt           0.0579
_refine_ls_wR_factor_ref         0.1078
_refine_ls_wR_factor_gt          0.0936
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_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 0.23486(3) 0.45661(4) 0.05254(4) 0.05001(17) Uani 1 1 d . . . . .
N1 N 0.25658(18) 0.3021(2) -0.0131(3) 0.0515(8) Uani 1 1 d . . . . .
N2 N 0.31476(18) 0.2376(2) 0.0471(3) 0.0555(8) Uani 1 1 d . . . . .
N3 N 0.21497(17) 0.6193(3) 0.1246(2) 0.0521(8) Uani 1 1 d . . . . .
N4 N 0.30030(16) 0.5893(2) -0.0410(2) 0.0474(7) Uani 1 1 d . . . . .
O1 O 0.31348(14) 0.3999(2) 0.17613(19) 0.0578(7) Uani 1 1 d . . . . .
O2 O 0.14232(14) 0.4687(2) -0.0446(2) 0.0659(7) Uani 1 1 d . . . . .
O3 O -0.0321(2) 0.4159(4) -0.3781(4) 0.1085(11) Uani 1 1 d . . . . .
C1 C 0.3394(2) 0.2961(3) 0.1444(3) 0.0486(9) Uani 1 1 d . . . . .
C2 C 0.4002(2) 0.2359(3) 0.2210(3) 0.0521(10) Uani 1 1 d . . . . .
C3 C 0.4221(2) 0.2776(4) 0.3316(4) 0.0688(12) Uani 1 1 d . . . . .
H3 H 0.3994 0.3459 0.3585 0.083 Uiso 1 1 calc R U . . .
C4 C 0.4774(3) 0.2197(5) 0.4036(4) 0.0868(15) Uani 1 1 d . . . . .
H4 H 0.4917 0.2493 0.4786 0.104 Uiso 1 1 calc R U . . .
C5 C 0.5115(3) 0.1197(5) 0.3664(5) 0.0853(14) Uani 1 1 d . . . . .
H5 H 0.5490 0.0814 0.4153 0.102 Uiso 1 1 calc R U . . .
C6 C 0.4901(2) 0.0762(4) 0.2564(5) 0.0741(13) Uani 1 1 d . . . . .
H6 H 0.5131 0.0078 0.2303 0.089 Uiso 1 1 calc R U . . .
C7 C 0.4350(2) 0.1328(3) 0.1845(3) 0.0606(11) Uani 1 1 d . . . . .
H7 H 0.4205 0.1019 0.1100 0.073 Uiso 1 1 calc R U . . .
C8 C 0.2243(3) 0.2579(3) -0.1104(4) 0.0621(11) Uani 1 1 d . . . . .
H8 H 0.2445 0.1883 -0.1393 0.075 Uiso 1 1 calc R U . . .
C9 C 0.1611(2) 0.3066(3) -0.1760(3) 0.0586(11) Uani 1 1 d . . . . .
C10 C 0.1208(2) 0.4053(3) -0.1383(3) 0.0535(10) Uani 1 1 d . . . . .
C11 C 0.0557(2) 0.4386(4) -0.2084(4) 0.0704(12) Uani 1 1 d . . . . .
H11 H 0.0281 0.5025 -0.1841 0.085 Uiso 1 1 calc R U . . .
C12 C 0.0313(3) 0.3806(5) -0.3108(5) 0.0815(14) Uani 1 1 d . . . . .
C13 C 0.0704(4) 0.2864(5) -0.3485(4) 0.0986(17) Uani 1 1 d . . . . .
H13 H 0.0541 0.2474 -0.4188 0.118 Uiso 1 1 calc R U . . .
C14 C 0.1335(3) 0.2498(4) -0.2825(4) 0.0959(16) Uani 1 1 d . . . . .
H14 H 0.1594 0.1848 -0.3086 0.115 Uiso 1 1 calc R U . . .
C15A C -0.0595(5) 0.5447(9) -0.3787(9) 0.102(3) Uani 0.52 1 d . . P A 1
H15A H -0.0792 0.5601 -0.3083 0.153 Uiso 0.52 1 calc R U P A 1
H15B H -0.0968 0.5563 -0.4443 0.153 Uiso 0.52 1 calc R U P A 1
H15C H -0.0202 0.6008 -0.3839 0.153 Uiso 0.52 1 calc R U P A 1
C15B C -0.0514(7) 0.3594(15) -0.4820(11) 0.163(7) Uani 0.48 1 d . . P A 2
H15D H -0.0149 0.3745 -0.5308 0.244 Uiso 0.48 1 calc R U P A 2
H15E H -0.0972 0.3912 -0.5188 0.244 Uiso 0.48 1 calc R U P A 2
H15F H -0.0556 0.2724 -0.4700 0.244 Uiso 0.48 1 calc R U P A 2
C16 C 0.1717(2) 0.6340(4) 0.2044(3) 0.0745(13) Uani 1 1 d . . . . .
H16 H 0.1521 0.5647 0.2352 0.089 Uiso 1 1 calc R U . . .
C17 C 0.1543(3) 0.7511(5) 0.2441(4) 0.0944(16) Uani 1 1 d . . . . .
H17 H 0.1246 0.7590 0.3012 0.113 Uiso 1 1 calc R U . . .
C18 C 0.1816(3) 0.8518(4) 0.1980(5) 0.0909(16) Uani 1 1 d . . . . .
H18 H 0.1703 0.9296 0.2236 0.109 Uiso 1 1 calc R U . . .
C19 C 0.2260(2) 0.8411(3) 0.1130(4) 0.0656(11) Uani 1 1 d . . . . .
C20 C 0.2560(3) 0.9442(3) 0.0610(5) 0.0831(14) Uani 1 1 d . . . . .
H20 H 0.2460 1.0234 0.0846 0.100 Uiso 1 1 calc R U . . .
C21 C 0.2980(3) 0.9286(4) -0.0204(5) 0.0826(14) Uani 1 1 d . . . . .
H21 H 0.3168 0.9977 -0.0529 0.099 Uiso 1 1 calc R U . . .
C22 C 0.3154(2) 0.8097(3) -0.0600(4) 0.0617(11) Uani 1 1 d . . . . .
C23 C 0.3579(2) 0.7880(5) -0.1464(4) 0.0806(14) Uani 1 1 d . . . . .
H23 H 0.3765 0.8540 -0.1837 0.097 Uiso 1 1 calc R U . . .
C24 C 0.3723(2) 0.6723(5) -0.1764(4) 0.0803(14) Uani 1 1 d . . . . .
H24 H 0.4023 0.6575 -0.2322 0.096 Uiso 1 1 calc R U . . .
C25 C 0.3418(2) 0.5752(4) -0.1230(3) 0.0623(11) Uani 1 1 d . . . . .
H25 H 0.3512 0.4956 -0.1462 0.075 Uiso 1 1 calc R U . . .
C26 C 0.28732(19) 0.7055(3) -0.0093(3) 0.0456(9) Uani 1 1 d . . . . .
C27 C 0.2418(2) 0.7212(3) 0.0787(3) 0.0494(9) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 N1 1.911(3) . ?
Cu1 O2 1.917(3) . ?
Cu1 O1 1.989(3) . ?
Cu1 N3 2.013(3) . ?
Cu1 N4 2.266(3) . ?
N1 C8 1.292(5) . ?
N1 N2 1.387(4) . ?
N2 C1 1.319(4) . ?
N3 C16 1.326(4) . ?
N3 C27 1.356(4) . ?
N4 C25 1.322(4) . ?
N4 C26 1.346(4) . ?
O1 C1 1.301(4) . ?
O2 C10 1.301(4) . ?
O3 C15B 1.355(13) . ?
O3 C12 1.369(5) . ?
O3 C15A 1.488(9) . ?
C1 C2 1.484(5) . ?
C2 C3 1.367(5) . ?
C2 C7 1.390(5) . ?
C3 C4 1.379(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.360(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.365(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.369(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.405(5) . ?
C8 H8 0.9300 . ?
C9 C14 1.410(6) . ?
C9 C10 1.415(5) . ?
C10 C11 1.403(5) . ?
C11 C12 1.365(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.365(6) . ?
C13 C14 1.362(7) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15A H15A 0.9600 . ?
C15A H15B 0.9600 . ?
C15A H15C 0.9600 . ?
C15B H15D 0.9600 . ?
C15B H15E 0.9600 . ?
C15B H15F 0.9600 . ?
C16 C17 1.406(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.350(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.383(6) . ?
C18 H18 0.9300 . ?
C19 C27 1.406(4) . ?
C19 C20 1.425(6) . ?
C20 C21 1.325(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.424(5) . ?
C21 H21 0.9300 . ?
C22 C23 1.388(6) . ?
C22 C26 1.412(5) . ?
C23 C24 1.342(6) . ?
C23 H23 0.9300 . ?
C24 C25 1.387(5) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
C26 C27 1.432(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 Cu1 O2 92.85(13) . . ?
N1 Cu1 O1 80.81(12) . . ?
O2 Cu1 O1 161.01(10) . . ?
N1 Cu1 N3 178.27(14) . . ?
O2 Cu1 N3 88.87(12) . . ?
O1 Cu1 N3 97.58(11) . . ?
N1 Cu1 N4 101.91(11) . . ?
O2 Cu1 N4 99.94(11) . . ?
O1 Cu1 N4 98.88(10) . . ?
N3 Cu1 N4 77.68(11) . . ?
C8 N1 N2 118.7(3) . . ?
C8 N1 Cu1 125.3(3) . . ?
N2 N1 Cu1 115.9(2) . . ?
C1 N2 N1 109.6(3) . . ?
C16 N3 C27 118.3(3) . . ?
C16 N3 Cu1 124.4(3) . . ?
C27 N3 Cu1 116.8(2) . . ?
C25 N4 C26 117.0(3) . . ?
C25 N4 Cu1 133.3(2) . . ?
C26 N4 Cu1 109.5(2) . . ?
C1 O1 Cu1 109.1(2) . . ?
C10 O2 Cu1 126.5(3) . . ?
C15B O3 C12 118.2(8) . . ?
C12 O3 C15A 122.1(5) . . ?
O1 C1 N2 124.4(4) . . ?
O1 C1 C2 119.5(3) . . ?
N2 C1 C2 116.1(3) . . ?
C3 C2 C7 117.9(4) . . ?
C3 C2 C1 120.8(4) . . ?
C7 C2 C1 121.2(4) . . ?
C2 C3 C4 120.7(4) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 120.8(5) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 119.3(4) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C7 120.3(4) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C6 C7 C2 121.0(4) . . ?
C6 C7 H7 119.5 . . ?
C2 C7 H7 119.5 . . ?
N1 C8 C9 125.3(4) . . ?
N1 C8 H8 117.3 . . ?
C9 C8 H8 117.3 . . ?
C8 C9 C14 118.6(4) . . ?
C8 C9 C10 123.7(4) . . ?
C14 C9 C10 117.6(4) . . ?
O2 C10 C11 118.8(4) . . ?
O2 C10 C9 123.3(4) . . ?
C11 C10 C9 117.9(4) . . ?
C12 C11 C10 122.3(5) . . ?
C12 C11 H11 118.9 . . ?
C10 C11 H11 118.9 . . ?
C11 C12 C13 120.2(5) . . ?
C11 C12 O3 121.0(5) . . ?
C13 C12 O3 118.8(5) . . ?
C14 C13 C12 119.6(5) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C9 122.6(5) . . ?
C13 C14 H14 118.7 . . ?
C9 C14 H14 118.7 . . ?
O3 C15A H15A 109.5 . . ?
O3 C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
O3 C15A H15C 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
O3 C15B H15D 109.5 . . ?
O3 C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
O3 C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
N3 C16 C17 122.1(4) . . ?
N3 C16 H16 119.0 . . ?
C17 C16 H16 119.0 . . ?
C18 C17 C16 119.0(4) . . ?
C18 C17 H17 120.5 . . ?
C16 C17 H17 120.5 . . ?
C17 C18 C19 121.0(4) . . ?
C17 C18 H18 119.5 . . ?
C19 C18 H18 119.5 . . ?
C18 C19 C27 116.9(4) . . ?
C18 C19 C20 123.4(4) . . ?
C27 C19 C20 119.7(4) . . ?
C21 C20 C19 120.8(4) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C20 C21 C22 122.2(4) . . ?
C20 C21 H21 118.9 . . ?
C22 C21 H21 118.9 . . ?
C23 C22 C26 116.9(4) . . ?
C23 C22 C21 124.7(4) . . ?
C26 C22 C21 118.5(4) . . ?
C24 C23 C22 120.3(4) . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C23 C24 C25 119.0(4) . . ?
C23 C24 H24 120.5 . . ?
C25 C24 H24 120.5 . . ?
N4 C25 C24 123.8(4) . . ?
N4 C25 H25 118.1 . . ?
C24 C25 H25 118.1 . . ?
N4 C26 C22 123.0(3) . . ?
N4 C26 C27 117.1(3) . . ?
C22 C26 C27 119.9(3) . . ?
N3 C27 C19 122.6(3) . . ?
N3 C27 C26 118.4(3) . . ?
C19 C27 C26 118.9(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 N2 C1 -179.0(3) . . . . ?
Cu1 N1 N2 C1 4.7(3) . . . . ?
Cu1 O1 C1 N2 -2.2(4) . . . . ?
Cu1 O1 C1 C2 178.6(2) . . . . ?
N1 N2 C1 O1 -1.5(4) . . . . ?
N1 N2 C1 C2 177.7(3) . . . . ?
O1 C1 C2 C3 9.8(5) . . . . ?
N2 C1 C2 C3 -169.4(3) . . . . ?
O1 C1 C2 C7 -172.5(3) . . . . ?
N2 C1 C2 C7 8.2(5) . . . . ?
C7 C2 C3 C4 0.7(6) . . . . ?
C1 C2 C3 C4 178.4(3) . . . . ?
C2 C3 C4 C5 0.0(7) . . . . ?
C3 C4 C5 C6 -0.4(7) . . . . ?
C4 C5 C6 C7 0.1(7) . . . . ?
C5 C6 C7 C2 0.6(6) . . . . ?
C3 C2 C7 C6 -1.0(5) . . . . ?
C1 C2 C7 C6 -178.8(3) . . . . ?
N2 N1 C8 C9 174.3(3) . . . . ?
Cu1 N1 C8 C9 -9.8(5) . . . . ?
N1 C8 C9 C14 178.2(4) . . . . ?
N1 C8 C9 C10 -5.8(6) . . . . ?
Cu1 O2 C10 C11 -170.6(2) . . . . ?
Cu1 O2 C10 C9 7.0(5) . . . . ?
C8 C9 C10 O2 7.3(5) . . . . ?
C14 C9 C10 O2 -176.7(4) . . . . ?
C8 C9 C10 C11 -175.1(3) . . . . ?
C14 C9 C10 C11 0.9(5) . . . . ?
O2 C10 C11 C12 176.7(3) . . . . ?
C9 C10 C11 C12 -1.0(5) . . . . ?
C10 C11 C12 C13 0.2(6) . . . . ?
C10 C11 C12 O3 -179.3(3) . . . . ?
C15B O3 C12 C11 176.4(7) . . . . ?
C15A O3 C12 C11 29.0(7) . . . . ?
C15B O3 C12 C13 -3.1(9) . . . . ?
C15A O3 C12 C13 -150.4(6) . . . . ?
C11 C12 C13 C14 0.8(7) . . . . ?
O3 C12 C13 C14 -179.8(4) . . . . ?
C12 C13 C14 C9 -0.8(8) . . . . ?
C8 C9 C14 C13 176.2(4) . . . . ?
C10 C9 C14 C13 -0.1(7) . . . . ?
C27 N3 C16 C17 -1.4(6) . . . . ?
Cu1 N3 C16 C17 -174.0(3) . . . . ?
N3 C16 C17 C18 1.2(7) . . . . ?
C16 C17 C18 C19 -0.1(8) . . . . ?
C17 C18 C19 C27 -0.7(7) . . . . ?
C17 C18 C19 C20 179.8(5) . . . . ?
C18 C19 C20 C21 -179.7(4) . . . . ?
C27 C19 C20 C21 0.8(7) . . . . ?
C19 C20 C21 C22 -0.1(7) . . . . ?
C20 C21 C22 C23 178.7(4) . . . . ?
C20 C21 C22 C26 -0.6(7) . . . . ?
C26 C22 C23 C24 -1.7(6) . . . . ?
C21 C22 C23 C24 178.9(4) . . . . ?
C22 C23 C24 C25 2.4(7) . . . . ?
C26 N4 C25 C24 0.3(6) . . . . ?
Cu1 N4 C25 C24 173.9(3) . . . . ?
C23 C24 C25 N4 -1.8(7) . . . . ?
C25 N4 C26 C22 0.5(5) . . . . ?
Cu1 N4 C26 C22 -174.6(3) . . . . ?
C25 N4 C26 C27 179.5(3) . . . . ?
Cu1 N4 C26 C27 4.4(4) . . . . ?
C23 C22 C26 N4 0.2(6) . . . . ?
C21 C22 C26 N4 179.6(4) . . . . ?
C23 C22 C26 C27 -178.8(4) . . . . ?
C21 C22 C26 C27 0.7(5) . . . . ?
C16 N3 C27 C19 0.4(6) . . . . ?
Cu1 N3 C27 C19 173.6(3) . . . . ?
C16 N3 C27 C26 -178.6(3) . . . . ?
Cu1 N3 C27 C26 -5.5(4) . . . . ?
C18 C19 C27 N3 0.6(6) . . . . ?
C20 C19 C27 N3 -179.9(4) . . . . ?
C18 C19 C27 C26 179.7(4) . . . . ?
C20 C19 C27 C26 -0.8(6) . . . . ?
N4 C26 C27 N3 0.1(5) . . . . ?
C22 C26 C27 N3 179.2(3) . . . . ?
N4 C26 C27 C19 -179.0(3) . . . . ?
C22 C26 C27 C19 0.1(5) . . . . ?

_refine_diff_density_max         0.338
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.054

