# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 941486'
_audit_update_record             
;
2016-01-27 deposited with the CCDC.
2016-02-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H26 Cu N3 O5 S, C7 H7 O3 S'
_chemical_formula_sum            'C35 H33 Cu N3 O8 S2'
_chemical_formula_weight         751.07


loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.3200 1.2650 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1250 0.1230 '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                   8.2850(4)
_cell_length_b                   31.1469(17)
_cell_length_c                   13.8987(7)
_cell_angle_alpha                90
_cell_angle_beta                 112.888(3)
_cell_angle_gamma                90
_cell_volume                     3304.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_F_000             1556
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.846
_shelx_estimated_absorpt_T_min   0.774
_shelx_estimated_absorpt_T_max   0.913
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.808
_exptl_absorpt_correction_T_max  0.911
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            49899
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -40
_diffrn_reflns_limit_k_max       41
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.526
_diffrn_reflns_theta_max         28.284
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             8145
_reflns_number_gt                6516
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1999)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0399P)²+2.2116P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8145
_refine_ls_number_parameters     444
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.0964
_refine_ls_wR_factor_gt          0.0886
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.0914(3) 0.66763(7) 0.59195(18) 0.0394(5) Uani 1 1 d . . . . .
H1 H 1.0100 0.6454 0.5748 0.047 Uiso 1 1 calc R U . . .
C2 C 1.2673(3) 0.65744(7) 0.62840(19) 0.0437(5) Uani 1 1 d . . . . .
H2 H 1.3036 0.6290 0.6348 0.052 Uiso 1 1 calc R U . . .
C3 C 1.3876(3) 0.69023(7) 0.65509(19) 0.0420(5) Uani 1 1 d . . . . .
H3 H 1.5069 0.6842 0.6810 0.050 Uiso 1 1 calc R U . . .
C4 C 1.3302(3) 0.73212(7) 0.64322(17) 0.0366(4) Uani 1 1 d . . . . .
H4 H 1.4099 0.7547 0.6606 0.044 Uiso 1 1 calc R U . . .
C5 C 1.1523(2) 0.73999(6) 0.60508(15) 0.0298(4) Uani 1 1 d . . . . .
C6 C 1.0738(2) 0.78336(6) 0.58284(15) 0.0297(4) Uani 1 1 d . . . . .
C7 C 1.1622(3) 0.82186(6) 0.59775(16) 0.0327(4) Uani 1 1 d . . . . .
H7 H 1.2839 0.8225 0.6290 0.039 Uiso 1 1 calc R U . . .
C8 C 1.0675(3) 0.85987(6) 0.56559(15) 0.0321(4) Uani 1 1 d . . . . .
C9 C 0.8850(3) 0.85743(6) 0.51926(15) 0.0331(4) Uani 1 1 d . . . . .
H9 H 0.8186 0.8822 0.4958 0.040 Uiso 1 1 calc R U . . .
C10 C 0.8037(2) 0.81795(6) 0.50848(15) 0.0298(4) Uani 1 1 d . . . . .
C11 C 0.6135(3) 0.80910(7) 0.46118(15) 0.0319(4) Uani 1 1 d . . . . .
C12 C 0.4861(3) 0.83997(8) 0.41564(17) 0.0409(5) Uani 1 1 d . . . . .
H12 H 0.5170 0.8684 0.4109 0.049 Uiso 1 1 calc R U . . .
C13 C 0.3118(3) 0.82768(9) 0.37736(18) 0.0486(6) Uani 1 1 d . . . . .
H13 H 0.2239 0.8480 0.3481 0.058 Uiso 1 1 calc R U . . .
C14 C 0.2695(3) 0.78548(9) 0.38286(19) 0.0483(6) Uani 1 1 d . . . . .
H14 H 0.1530 0.7768 0.3574 0.058 Uiso 1 1 calc R U . . .
C15 C 0.4029(3) 0.75613(8) 0.42681(17) 0.0412(5) Uani 1 1 d . . . . .
H15 H 0.3745 0.7274 0.4296 0.049 Uiso 1 1 calc R U . . .
C16 C 1.1586(3) 0.90163(6) 0.57782(16) 0.0366(4) Uani 1 1 d . . . . .
C17 C 1.0787(4) 0.93945(7) 0.5884(2) 0.0506(6) Uani 1 1 d . . . . .
H17 H 0.9665 0.9385 0.5884 0.061 Uiso 1 1 calc R U . . .
C18 C 1.1622(4) 0.97834(8) 0.5987(2) 0.0652(8) Uani 1 1 d . . . . .
H18 H 1.1077 1.0033 0.6075 0.078 Uiso 1 1 calc R U . . .
C19 C 1.3254(4) 0.98044(9) 0.5960(2) 0.0696(9) Uani 1 1 d . . . . .
H19 H 1.3802 1.0069 0.6006 0.084 Uiso 1 1 calc R U . . .
C20 C 1.4083(4) 0.94334(9) 0.5866(2) 0.0606(7) Uani 1 1 d . . . . .
H20 H 1.5196 0.9447 0.5854 0.073 Uiso 1 1 calc R U . . .
C21 C 1.3267(3) 0.90391(8) 0.57875(18) 0.0455(5) Uani 1 1 d . . . . .
H21 H 1.3846 0.8789 0.5741 0.055 Uiso 1 1 calc R U . . .
C31 C 0.8808(3) 0.64208(7) 0.30597(16) 0.0337(4) Uani 1 1 d . . . . .
C32 C 1.0406(3) 0.66085(8) 0.3244(2) 0.0497(6) Uani 1 1 d . . . . .
H32 H 1.0501 0.6906 0.3236 0.060 Uiso 1 1 calc R U . . .
C33 C 1.1863(3) 0.63556(9) 0.3440(2) 0.0564(7) Uani 1 1 d . . . . .
H33 H 1.2934 0.6486 0.3559 0.068 Uiso 1 1 calc R U . . .
C34 C 1.1774(3) 0.59165(9) 0.34642(19) 0.0493(6) Uani 1 1 d . . . . .
C35 C 1.0160(4) 0.57316(9) 0.3250(2) 0.0595(7) Uani 1 1 d . . . . .
H35 H 1.0062 0.5434 0.3238 0.071 Uiso 1 1 calc R U . . .
C36 C 0.8679(3) 0.59815(8) 0.3053(2) 0.0524(6) Uani 1 1 d . . . . .
H36 H 0.7602 0.5852 0.2916 0.063 Uiso 1 1 calc R U . . .
C37 C 1.3401(4) 0.56474(11) 0.3696(3) 0.0724(9) Uani 1 1 d . . . . .
H37A H 1.3085 0.5349 0.3605 0.109 Uiso 1 1 calc R U . . .
H37B H 1.4201 0.5696 0.4403 0.109 Uiso 1 1 calc R U . . .
H37C H 1.3951 0.5726 0.3228 0.109 Uiso 1 1 calc R U . . .
C41 C 0.9306(3) 0.92485(6) 0.21344(16) 0.0354(4) Uani 1 1 d . . . . .
C42 C 1.0867(3) 0.93593(8) 0.29364(19) 0.0494(6) Uani 1 1 d . . . . .
H42 H 1.1037 0.9302 0.3626 0.059 Uiso 1 1 calc R U . . .
C43 C 1.2169(3) 0.95540(9) 0.2709(2) 0.0561(7) Uani 1 1 d . . . . .
H43 H 1.3214 0.9628 0.3253 0.067 Uiso 1 1 calc R U . . .
C44 C 1.1964(3) 0.96418(7) 0.1699(2) 0.0479(6) Uani 1 1 d . . . . .
C45 C 1.0387(3) 0.95378(8) 0.0912(2) 0.0491(6) Uani 1 1 d . . . . .
H45 H 1.0211 0.9599 0.0224 0.059 Uiso 1 1 calc R U . . .
C46 C 0.9061(3) 0.93445(7) 0.11245(18) 0.0442(5) Uani 1 1 d . . . . .
H46 H 0.8002 0.9280 0.0582 0.053 Uiso 1 1 calc R U . . .
C47 C 1.3424(4) 0.98430(10) 0.1452(3) 0.0706(8) Uani 1 1 d . . . . .
H47A H 1.2991 0.9917 0.0725 0.106 Uiso 1 1 calc R U . . .
H47B H 1.4371 0.9642 0.1609 0.106 Uiso 1 1 calc R U . . .
H47C H 1.3835 1.0097 0.1867 0.106 Uiso 1 1 calc R U . . .
Cu1 Cu 0.78141(3) 0.72832(2) 0.53085(2) 0.03309(8) Uani 1 1 d . . . . .
N1 N 1.0339(2) 0.70784(5) 0.58034(13) 0.0329(4) Uani 1 1 d . . . . .
N2 N 0.8985(2) 0.78240(5) 0.54061(13) 0.0300(3) Uani 1 1 d . . . . .
N3 N 0.5715(2) 0.76767(5) 0.46548(13) 0.0327(4) Uani 1 1 d . . . . .
O1 O 0.8180(2) 0.72540(5) 0.70479(13) 0.0478(4) Uani 1 1 d . . . . .
H1A H 0.8320 0.6995 0.7254 0.072 Uiso 1 1 d R U . . .
H1B H 0.7799 0.7430 0.7378 0.072 Uiso 1 1 d R U . . .
O2 O 0.6538(2) 0.67428(5) 0.51066(12) 0.0439(4) Uani 1 1 d . . . . .
H2A H 0.6755 0.6625 0.5696 0.066 Uiso 1 1 d R U . . .
H2B H 0.6275 0.6623 0.4515 0.066 Uiso 1 1 d R U . . .
O3 O 0.6156(2) 0.68169(6) 0.16952(12) 0.0504(4) Uani 1 1 d . . . . .
O4 O 0.5796(2) 0.64982(5) 0.31809(12) 0.0455(4) Uani 1 1 d . . . . .
O5 O 0.7559(2) 0.71375(5) 0.33989(12) 0.0430(4) Uani 1 1 d . . . . .
O6 O 0.8647(2) 0.85537(5) 0.28965(13) 0.0508(4) Uani 1 1 d . . . . .
O7 O 0.7205(2) 0.91974(5) 0.31195(13) 0.0511(4) Uani 1 1 d . . . . .
O8 O 0.6319(2) 0.88660(5) 0.14131(13) 0.0460(4) Uani 1 1 d . . . . .
S1 S 0.69365(6) 0.67425(2) 0.28051(4) 0.03460(12) Uani 1 1 d . . . . .
S2 S 0.77355(7) 0.89475(2) 0.24212(4) 0.03696(12) 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
C1 N1 1.327(3) . ?
C1 C2 1.381(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.374(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.377(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(3) . ?
C4 H4 0.9300 . ?
C5 N1 1.349(2) . ?
C5 C6 1.478(3) . ?
C6 N2 1.339(2) . ?
C6 C7 1.378(3) . ?
C7 C8 1.394(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.396(3) . ?
C8 C16 1.480(3) . ?
C9 C10 1.382(3) . ?
C9 H9 0.9300 . ?
C10 N2 1.330(2) . ?
C10 C11 1.478(3) . ?
C11 N3 1.344(3) . ?
C11 C12 1.386(3) . ?
C12 C13 1.385(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.370(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.380(3) . ?
C14 H14 0.9300 . ?
C15 N3 1.337(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.387(3) . ?
C16 C21 1.390(3) . ?
C17 C18 1.375(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.368(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.377(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.386(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C31 C36 1.372(3) . ?
C31 C32 1.377(3) . ?
C31 S1 1.763(2) . ?
C32 C33 1.377(3) . ?
C32 H32 0.9300 . ?
C33 C34 1.371(4) . ?
C33 H33 0.9300 . ?
C34 C35 1.378(4) . ?
C34 C37 1.512(3) . ?
C35 C36 1.387(4) . ?
C35 H35 0.9300 . ?
C36 H36 0.9300 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C41 C46 1.371(3) . ?
C41 C42 1.383(3) . ?
C41 S2 1.770(2) . ?
C42 C43 1.377(3) . ?
C42 H42 0.9300 . ?
C43 C44 1.375(4) . ?
C43 H43 0.9300 . ?
C44 C45 1.377(4) . ?
C44 C47 1.515(3) . ?
C45 C46 1.381(3) . ?
C45 H45 0.9300 . ?
C46 H46 0.9300 . ?
C47 H47A 0.9600 . ?
C47 H47B 0.9600 . ?
C47 H47C 0.9600 . ?
Cu1 N2 1.9223(16) . ?
Cu1 O2 1.9490(15) . ?
Cu1 N3 2.0304(16) . ?
Cu1 N1 2.0339(16) . ?
Cu1 O1 2.3182(16) . ?
Cu1 O5 2.6189(16) . ?
O1 H1A 0.8500 . ?
O1 H1B 0.8500 . ?
O2 H2A 0.8501 . ?
O2 H2B 0.8500 . ?
O3 S1 1.4407(16) . ?
O4 S1 1.4589(15) . ?
O5 S1 1.4591(16) . ?
O6 S2 1.4573(17) . ?
O7 S2 1.4397(17) . ?
O8 S2 1.4581(16) . ?

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 C1 C2 122.6(2) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C3 C2 C1 118.7(2) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 119.46(19) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C3 C4 C5 118.80(19) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 121.85(18) . . ?
N1 C5 C6 114.09(16) . . ?
C4 C5 C6 124.00(17) . . ?
N2 C6 C7 120.51(17) . . ?
N2 C6 C5 112.65(17) . . ?
C7 C6 C5 126.79(17) . . ?
C6 C7 C8 119.39(18) . . ?
C6 C7 H7 120.3 . . ?
C8 C7 H7 120.3 . . ?
C7 C8 C9 118.36(18) . . ?
C7 C8 C16 120.76(18) . . ?
C9 C8 C16 120.86(18) . . ?
C10 C9 C8 119.56(18) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
N2 C10 C9 120.31(18) . . ?
N2 C10 C11 112.47(17) . . ?
C9 C10 C11 127.20(17) . . ?
N3 C11 C12 121.49(19) . . ?
N3 C11 C10 114.13(17) . . ?
C12 C11 C10 124.38(19) . . ?
C13 C12 C11 118.6(2) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C14 C13 C12 119.7(2) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 118.8(2) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
N3 C15 C14 122.1(2) . . ?
N3 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
C17 C16 C21 118.3(2) . . ?
C17 C16 C8 121.0(2) . . ?
C21 C16 C8 120.68(19) . . ?
C18 C17 C16 121.2(3) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C19 C18 C17 120.1(3) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C20 119.8(2) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C19 C20 C21 120.3(3) . . ?
C19 C20 H20 119.8 . . ?
C21 C20 H20 119.8 . . ?
C20 C21 C16 120.2(2) . . ?
C20 C21 H21 119.9 . . ?
C16 C21 H21 119.9 . . ?
C36 C31 C32 119.4(2) . . ?
C36 C31 S1 120.38(17) . . ?
C32 C31 S1 120.20(17) . . ?
C33 C32 C31 120.0(2) . . ?
C33 C32 H32 120.0 . . ?
C31 C32 H32 120.0 . . ?
C34 C33 C32 121.6(2) . . ?
C34 C33 H33 119.2 . . ?
C32 C33 H33 119.2 . . ?
C33 C34 C35 118.0(2) . . ?
C33 C34 C37 120.4(3) . . ?
C35 C34 C37 121.6(3) . . ?
C34 C35 C36 121.2(2) . . ?
C34 C35 H35 119.4 . . ?
C36 C35 H35 119.4 . . ?
C31 C36 C35 119.9(2) . . ?
C31 C36 H36 120.1 . . ?
C35 C36 H36 120.1 . . ?
C34 C37 H37A 109.5 . . ?
C34 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
C34 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
C46 C41 C42 119.3(2) . . ?
C46 C41 S2 121.14(17) . . ?
C42 C41 S2 119.31(17) . . ?
C43 C42 C41 119.7(2) . . ?
C43 C42 H42 120.1 . . ?
C41 C42 H42 120.1 . . ?
C44 C43 C42 121.7(2) . . ?
C44 C43 H43 119.2 . . ?
C42 C43 H43 119.2 . . ?
C43 C44 C45 117.8(2) . . ?
C43 C44 C47 121.4(2) . . ?
C45 C44 C47 120.8(3) . . ?
C44 C45 C46 121.4(2) . . ?
C44 C45 H45 119.3 . . ?
C46 C45 H45 119.3 . . ?
C41 C46 C45 120.0(2) . . ?
C41 C46 H46 120.0 . . ?
C45 C46 H46 120.0 . . ?
C44 C47 H47A 109.5 . . ?
C44 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
C44 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
N2 Cu1 O2 176.02(7) . . ?
N2 Cu1 N3 79.83(7) . . ?
O2 Cu1 N3 97.74(7) . . ?
N2 Cu1 N1 80.01(7) . . ?
O2 Cu1 N1 101.94(7) . . ?
N3 Cu1 N1 158.40(7) . . ?
N2 Cu1 O1 95.91(6) . . ?
O2 Cu1 O1 87.71(6) . . ?
N3 Cu1 O1 103.43(6) . . ?
N1 Cu1 O1 86.26(6) . . ?
N2 Cu1 O5 93.61(6) . . ?
O2 Cu1 O5 83.05(6) . . ?
N3 Cu1 O5 86.19(6) . . ?
N1 Cu1 O5 87.44(6) . . ?
O1 Cu1 O5 167.50(5) . . ?
C1 N1 C5 118.57(17) . . ?
C1 N1 Cu1 127.63(14) . . ?
C5 N1 Cu1 113.78(13) . . ?
C10 N2 C6 121.81(17) . . ?
C10 N2 Cu1 119.32(13) . . ?
C6 N2 Cu1 118.83(13) . . ?
C15 N3 C11 119.24(18) . . ?
C15 N3 Cu1 126.65(15) . . ?
C11 N3 Cu1 114.10(13) . . ?
Cu1 O1 H1A 109.5 . . ?
Cu1 O1 H1B 127.7 . . ?
H1A O1 H1B 117.5 . . ?
Cu1 O2 H2A 109.5 . . ?
Cu1 O2 H2B 116.0 . . ?
H2A O2 H2B 128.4 . . ?
S1 O5 Cu1 126.21(9) . . ?
O3 S1 O4 112.58(10) . . ?
O3 S1 O5 112.50(10) . . ?
O4 S1 O5 111.89(9) . . ?
O3 S1 C31 107.44(10) . . ?
O4 S1 C31 105.86(10) . . ?
O5 S1 C31 106.02(10) . . ?
O7 S2 O6 112.95(11) . . ?
O7 S2 O8 113.53(11) . . ?
O6 S2 O8 111.76(10) . . ?
O7 S2 C41 108.01(10) . . ?
O6 S2 C41 104.54(10) . . ?
O8 S2 C41 105.26(10) . . ?

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
C4 H4 O3 0.93 2.58 3.501(3) 168.7 4_676
C7 H7 O3 0.93 2.59 3.494(3) 165.5 4_676
C9 H9 O7 0.93 2.63 3.297(3) 128.7 .
O1 H1A O6 0.85 1.90 2.741(2) 171.9 4_576
O1 H1A S2 0.85 3.00 3.8156(16) 162.1 4_576
O1 H1B O5 0.85 2.02 2.852(2) 165.1 4_576
O1 H1B S1 0.85 2.80 3.5752(16) 152.5 4_576
O2 H2A O8 0.85 1.94 2.680(2) 145.6 4_576
O2 H2A S2 0.85 2.84 3.6706(16) 165.3 4_576
O2 H2B O4 0.85 1.78 2.616(2) 166.3 .
O2 H2B S1 0.85 2.67 3.3411(16) 137.5 .

_refine_diff_density_max         0.352
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.057

_shelxl_version_number           2014-3

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

data_2
_database_code_depnum_ccdc_archive 'CCDC 941487'
_audit_update_record             
;
2016-01-27 deposited with the CCDC.
2016-02-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C35 H25 Cu N3 O4'
_chemical_formula_sum            'C35 H25 Cu N3 O4'
_chemical_formula_weight         614.93

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.3200 1.2650 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5993(6)
_cell_length_b                   10.8157(7)
_cell_length_c                   14.9401(9)
_cell_angle_alpha                95.613(3)
_cell_angle_beta                 90.814(4)
_cell_angle_gamma                114.820(3)
_cell_volume                     1398.48(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.460
_exptl_crystal_F_000             634
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.828
_shelx_estimated_absorpt_T_min   0.789
_shelx_estimated_absorpt_T_max   0.893
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.812
_exptl_absorpt_correction_T_max  0.891
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23797
_diffrn_reflns_av_unetI/netI     0.0281
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.342
_diffrn_reflns_theta_max         30.160
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.943
_diffrn_measured_fraction_theta_full 0.952
_diffrn_reflns_Laue_measured_fraction_max 0.943
_diffrn_reflns_Laue_measured_fraction_full 0.952
_diffrn_reflns_point_group_measured_fraction_max 0.943
_diffrn_reflns_point_group_measured_fraction_full 0.952
_reflns_number_total             7815
_reflns_number_gt                6069
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1999)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0568P)²+0.6412P] 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         7815
_refine_ls_number_parameters     388
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0409
_refine_ls_wR_factor_ref         0.1203
_refine_ls_wR_factor_gt          0.1041
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
C1 C -0.0518(3) 0.0052(2) 0.28540(14) 0.0435(5) Uani 1 1 d . . . . .
H1 H -0.0130 -0.0170 0.2326 0.052 Uiso 1 1 calc R U . . .
C2 C -0.2097(3) -0.0465(2) 0.29160(16) 0.0492(5) Uani 1 1 d . . . . .
H2 H -0.2757 -0.1014 0.2431 0.059 Uiso 1 1 calc R U . . .
C3 C -0.2675(2) -0.0163(2) 0.36952(16) 0.0463(5) Uani 1 1 d . . . . .
H3 H -0.3732 -0.0514 0.3751 0.056 Uiso 1 1 calc R U . . .
C4 C -0.1663(2) 0.0678(2) 0.44044(14) 0.0381(4) Uani 1 1 d . . . . .
H4 H -0.2030 0.0894 0.4942 0.046 Uiso 1 1 calc R U . . .
C5 C -0.0101(2) 0.11858(18) 0.42948(12) 0.0324(3) Uani 1 1 d . . . . .
C6 C 0.1098(2) 0.21047(18) 0.49943(12) 0.0311(3) Uani 1 1 d . . . . .
C7 C 0.0866(2) 0.2603(2) 0.58381(13) 0.0351(4) Uani 1 1 d . . . . .
H7 H -0.0127 0.2386 0.6015 0.042 Uiso 1 1 calc R U . . .
C8 C 0.2139(2) 0.34389(19) 0.64299(12) 0.0340(4) Uani 1 1 d . . . . .
C9 C 0.3606(2) 0.3719(2) 0.61321(13) 0.0358(4) Uani 1 1 d . . . . .
H9 H 0.4477 0.4270 0.6503 0.043 Uiso 1 1 calc R U . . .
C10 C 0.3750(2) 0.31726(18) 0.52835(12) 0.0316(3) Uani 1 1 d . . . . .
C11 C 0.5207(2) 0.33160(19) 0.48966(13) 0.0341(4) Uani 1 1 d . . . . .
C12 C 0.6623(2) 0.4014(2) 0.53611(15) 0.0434(4) Uani 1 1 d . . . . .
H12 H 0.6709 0.4445 0.5942 0.052 Uiso 1 1 calc R U . . .
C13 C 0.7915(2) 0.4054(3) 0.49353(18) 0.0518(5) Uani 1 1 d . . . . .
H13 H 0.8881 0.4500 0.5236 0.062 Uiso 1 1 calc R U . . .
C14 C 0.7765(3) 0.3435(3) 0.40732(18) 0.0518(6) Uani 1 1 d . . . . .
H14 H 0.8625 0.3474 0.3776 0.062 Uiso 1 1 calc R U . . .
C15 C 0.6312(2) 0.2753(2) 0.36529(16) 0.0439(5) Uani 1 1 d . . . . .
H15 H 0.6205 0.2323 0.3069 0.053 Uiso 1 1 calc R U . . .
C16 C 0.1969(2) 0.3972(2) 0.73532(13) 0.0394(4) Uani 1 1 d . . . . .
C17 C 0.3242(3) 0.4947(3) 0.78777(17) 0.0590(6) Uani 1 1 d . . . . .
H17 H 0.4202 0.5302 0.7637 0.071 Uiso 1 1 calc R U . . .
C18 C 0.3078(4) 0.5386(4) 0.87514(19) 0.0746(9) Uani 1 1 d . . . . .
H18 H 0.3933 0.6038 0.9094 0.089 Uiso 1 1 calc R U . . .
C19 C 0.1665(4) 0.4875(4) 0.91300(19) 0.0721(8) Uani 1 1 d . . . . .
H19 H 0.1574 0.5141 0.9729 0.086 Uiso 1 1 calc R U . . .
C20 C 0.0407(4) 0.3968(4) 0.8601(2) 0.0796(10) Uani 1 1 d . . . . .
H20 H -0.0560 0.3654 0.8834 0.095 Uiso 1 1 calc R U . . .
C21 C 0.0554(3) 0.3513(3) 0.77258(18) 0.0635(7) Uani 1 1 d . . . . .
H21 H -0.0315 0.2887 0.7381 0.076 Uiso 1 1 calc R U . . .
C31 C 0.3204(2) -0.0421(2) 0.27898(14) 0.0400(4) Uani 1 1 d . . . . .
C32 C 0.3766(2) -0.1238(2) 0.21393(13) 0.0393(4) Uani 1 1 d . . . . .
C33 C 0.4516(3) -0.0693(3) 0.13860(15) 0.0520(5) Uani 1 1 d . . . . .
H33 H 0.4636 0.0171 0.1263 0.062 Uiso 1 1 calc R U . . .
C34 C 0.5087(4) -0.1438(4) 0.08182(17) 0.0680(8) Uani 1 1 d . . . . .
H34 H 0.5607 -0.1065 0.0320 0.082 Uiso 1 1 calc R U . . .
C35 C 0.4889(4) -0.2722(3) 0.09873(19) 0.0656(8) Uani 1 1 d . . . . .
H35 H 0.5269 -0.3219 0.0601 0.079 Uiso 1 1 calc R U . . .
C36 C 0.4129(3) -0.3282(3) 0.1727(2) 0.0640(7) Uani 1 1 d . . . . .
H36 H 0.3988 -0.4157 0.1837 0.077 Uiso 1 1 calc R U . . .
C37 C 0.3580(3) -0.2537(2) 0.23014(18) 0.0518(5) Uani 1 1 d . . . . .
H37 H 0.3079 -0.2910 0.2804 0.062 Uiso 1 1 calc R U . . .
C41 C 0.1714(3) 0.3530(2) 0.26608(16) 0.0466(5) Uani 1 1 d . . . . .
C42 C 0.0976(3) 0.2869(2) 0.17326(17) 0.0485(5) Uani 1 1 d . . . . .
C43 C -0.0507(3) 0.2666(3) 0.1512(2) 0.0651(7) Uani 1 1 d . . . . .
H43 H -0.1038 0.2970 0.1929 0.078 Uiso 1 1 calc R U . . .
C44 C -0.1215(5) 0.2020(4) 0.0681(3) 0.0855(10) Uani 1 1 d . . . . .
H44 H -0.2221 0.1884 0.0542 0.103 Uiso 1 1 calc R U . . .
C45 C -0.0446(6) 0.1582(4) 0.0064(3) 0.1004(13) Uani 1 1 d . . . . .
H45 H -0.0924 0.1142 -0.0496 0.120 Uiso 1 1 calc R U . . .
C46 C 0.1051(6) 0.1793(5) 0.0273(3) 0.0976(12) Uani 1 1 d . . . . .
H46 H 0.1583 0.1505 -0.0153 0.117 Uiso 1 1 calc R U . . .
C47 C 0.1763(4) 0.2426(3) 0.1106(2) 0.0707(8) Uani 1 1 d . . . . .
H47 H 0.2765 0.2554 0.1245 0.085 Uiso 1 1 calc R U . . .
Cu1 Cu 0.28270(3) 0.17478(2) 0.35313(2) 0.03643(8) Uani 1 1 d . . . . .
N1 N 0.50509(18) 0.26878(17) 0.40568(12) 0.0371(3) Uani 1 1 d . . . . .
N2 N 0.25153(17) 0.24087(16) 0.47299(11) 0.0322(3) Uani 1 1 d . . . . .
N3 N 0.04629(19) 0.08587(17) 0.35314(11) 0.0367(3) Uani 1 1 d . . . . .
O1 O 0.31958(19) 0.06669(17) 0.25312(10) 0.0463(3) Uani 1 1 d . . . . .
O2 O 0.30034(17) 0.35387(17) 0.28592(11) 0.0491(4) Uani 1 1 d . . . . .
O3 O 0.2796(2) -0.0819(2) 0.35254(12) 0.0622(5) Uani 1 1 d . . . . .
O4 O 0.1001(2) 0.4001(3) 0.31689(14) 0.0709(6) 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
C1 N3 1.335(2) . ?
C1 C2 1.386(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.366(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.391(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9300 . ?
C5 N3 1.349(2) . ?
C5 C6 1.485(2) . ?
C6 N2 1.335(2) . ?
C6 C7 1.380(3) . ?
C7 C8 1.407(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.399(3) . ?
C8 C16 1.481(3) . ?
C9 C10 1.379(3) . ?
C9 H9 0.9300 . ?
C10 N2 1.337(2) . ?
C10 C11 1.475(2) . ?
C11 N1 1.342(3) . ?
C11 C12 1.381(3) . ?
C12 C13 1.388(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.368(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.380(3) . ?
C14 H14 0.9300 . ?
C15 N1 1.339(2) . ?
C15 H15 0.9300 . ?
C16 C21 1.383(3) . ?
C16 C17 1.396(3) . ?
C17 C18 1.379(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.385(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.368(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.382(4) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C31 O3 1.229(3) . ?
C31 O1 1.277(3) . ?
C31 C32 1.505(3) . ?
C31 Cu1 2.660(2) . ?
C32 C37 1.387(3) . ?
C32 C33 1.389(3) . ?
C33 C34 1.385(3) . ?
C33 H33 0.9300 . ?
C34 C35 1.370(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.380(5) . ?
C35 H35 0.9300 . ?
C36 C37 1.377(4) . ?
C36 H36 0.9300 . ?
C37 H37 0.9300 . ?
C41 O4 1.239(3) . ?
C41 O2 1.265(3) . ?
C41 C42 1.513(3) . ?
C42 C43 1.377(4) . ?
C42 C47 1.383(4) . ?
C43 C44 1.378(4) . ?
C43 H43 0.9300 . ?
C44 C45 1.359(6) . ?
C44 H44 0.9300 . ?
C45 C46 1.383(6) . ?
C45 H45 0.9300 . ?
C46 C47 1.379(5) . ?
C46 H46 0.9300 . ?
C47 H47 0.9300 . ?
Cu1 O1 1.9353(15) . ?
Cu1 N2 1.9368(16) . ?
Cu1 N1 2.0449(17) . ?
Cu1 N3 2.0597(17) . ?
Cu1 O2 2.2134(16) . ?

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
N3 C1 C2 121.9(2) . . ?
N3 C1 H1 119.1 . . ?
C2 C1 H1 119.1 . . ?
C3 C2 C1 119.42(19) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 119.15(19) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C5 C4 C3 118.73(19) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
N3 C5 C4 121.84(17) . . ?
N3 C5 C6 114.09(16) . . ?
C4 C5 C6 124.06(17) . . ?
N2 C6 C7 120.89(16) . . ?
N2 C6 C5 112.06(16) . . ?
C7 C6 C5 127.03(16) . . ?
C6 C7 C8 119.68(16) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C9 C8 C7 117.69(17) . . ?
C9 C8 C16 119.92(17) . . ?
C7 C8 C16 122.34(17) . . ?
C10 C9 C8 119.45(16) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
N2 C10 C9 121.28(16) . . ?
N2 C10 C11 113.09(16) . . ?
C9 C10 C11 125.62(16) . . ?
N1 C11 C12 122.22(18) . . ?
N1 C11 C10 114.57(16) . . ?
C12 C11 C10 123.20(18) . . ?
C11 C12 C13 118.1(2) . . ?
C11 C12 H12 121.0 . . ?
C13 C12 H12 121.0 . . ?
C14 C13 C12 119.9(2) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 118.7(2) . . ?
C13 C14 H14 120.7 . . ?
C15 C14 H14 120.7 . . ?
N1 C15 C14 122.2(2) . . ?
N1 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
C21 C16 C17 118.0(2) . . ?
C21 C16 C8 121.2(2) . . ?
C17 C16 C8 120.8(2) . . ?
C18 C17 C16 120.1(3) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C19 121.4(3) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
C20 C19 C18 118.4(3) . . ?
C20 C19 H19 120.8 . . ?
C18 C19 H19 120.8 . . ?
C19 C20 C21 120.9(3) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C20 C21 C16 121.2(3) . . ?
C20 C21 H21 119.4 . . ?
C16 C21 H21 119.4 . . ?
O3 C31 O1 124.2(2) . . ?
O3 C31 C32 119.4(2) . . ?
O1 C31 C32 116.46(18) . . ?
O3 C31 Cu1 81.64(13) . . ?
O1 C31 Cu1 43.09(9) . . ?
C32 C31 Cu1 157.75(15) . . ?
C37 C32 C33 119.0(2) . . ?
C37 C32 C31 120.1(2) . . ?
C33 C32 C31 120.9(2) . . ?
C34 C33 C32 120.0(2) . . ?
C34 C33 H33 120.0 . . ?
C32 C33 H33 120.0 . . ?
C35 C34 C33 120.2(3) . . ?
C35 C34 H34 119.9 . . ?
C33 C34 H34 119.9 . . ?
C34 C35 C36 120.4(2) . . ?
C34 C35 H35 119.8 . . ?
C36 C35 H35 119.8 . . ?
C37 C36 C35 119.6(3) . . ?
C37 C36 H36 120.2 . . ?
C35 C36 H36 120.2 . . ?
C36 C37 C32 120.8(2) . . ?
C36 C37 H37 119.6 . . ?
C32 C37 H37 119.6 . . ?
O4 C41 O2 125.3(2) . . ?
O4 C41 C42 117.6(2) . . ?
O2 C41 C42 117.1(2) . . ?
C43 C42 C47 119.2(3) . . ?
C43 C42 C41 120.1(2) . . ?
C47 C42 C41 120.6(2) . . ?
C42 C43 C44 120.8(3) . . ?
C42 C43 H43 119.6 . . ?
C44 C43 H43 119.6 . . ?
C45 C44 C43 120.1(4) . . ?
C45 C44 H44 120.0 . . ?
C43 C44 H44 120.0 . . ?
C44 C45 C46 119.7(3) . . ?
C44 C45 H45 120.1 . . ?
C46 C45 H45 120.1 . . ?
C47 C46 C45 120.6(4) . . ?
C47 C46 H46 119.7 . . ?
C45 C46 H46 119.7 . . ?
C46 C47 C42 119.6(3) . . ?
C46 C47 H47 120.2 . . ?
C42 C47 H47 120.2 . . ?
O1 Cu1 N2 162.58(7) . . ?
O1 Cu1 N1 96.23(7) . . ?
N2 Cu1 N1 79.87(6) . . ?
O1 Cu1 N3 102.15(7) . . ?
N2 Cu1 N3 78.75(6) . . ?
N1 Cu1 N3 157.56(7) . . ?
O1 Cu1 O2 99.84(7) . . ?
N2 Cu1 O2 97.36(7) . . ?
N1 Cu1 O2 93.62(6) . . ?
N3 Cu1 O2 95.80(6) . . ?
O1 Cu1 C31 26.79(7) . . ?
N2 Cu1 C31 135.86(7) . . ?
N1 Cu1 C31 92.27(6) . . ?
N3 Cu1 C31 98.32(7) . . ?
O2 Cu1 C31 126.60(7) . . ?
C15 N1 C11 118.82(18) . . ?
C15 N1 Cu1 127.38(15) . . ?
C11 N1 Cu1 113.79(12) . . ?
C6 N2 C10 120.96(16) . . ?
C6 N2 Cu1 120.52(12) . . ?
C10 N2 Cu1 118.52(12) . . ?
C1 N3 C5 118.97(17) . . ?
C1 N3 Cu1 126.52(15) . . ?
C5 N3 Cu1 114.48(12) . . ?
C31 O1 Cu1 110.12(13) . . ?
C41 O2 Cu1 113.47(14) . . ?

_refine_diff_density_max         0.452
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.059

_shelxl_version_number           2014-3

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

data_5rev
_database_code_depnum_ccdc_archive 'CCDC 941488'
_audit_update_record             
;
2016-01-27 deposited with the CCDC.
2016-02-05 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         'C35 H25 Cu N3 O6'
_chemical_formula_sum            'C35 H25 Cu N3 O6'
_chemical_formula_weight         646.93

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.3200 1.2650 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 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                   17.8398(14)
_cell_length_b                   9.0056(7)
_cell_length_c                   27.0152(17)
_cell_angle_alpha                90
_cell_angle_beta                 128.221(4)
_cell_angle_gamma                90
_cell_volume                     3409.8(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    43449
_cell_measurement_theta_min      2.457
_cell_measurement_theta_max      29.600

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_F_000             1332
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.298
_exptl_crystal_size_mid          0.209
_exptl_crystal_size_min          0.121
_exptl_absorpt_coefficient_mu    0.686
_shelx_estimated_absorpt_T_min   0.822
_shelx_estimated_absorpt_T_max   0.922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.840
_exptl_absorpt_correction_T_max  0.919
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            43449
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_av_R_equivalents  0.0240
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.457
_diffrn_reflns_theta_max         29.600
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             9495
_reflns_number_gt                6772
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1999)'
_computing_structure_refinement  'SHELXL-201/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0572P)²+0.9046P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9495
_refine_ls_number_parameters     437
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.1126
_refine_ls_wR_factor_gt          0.0986
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 -0.500 0.000 294 79 ' '
2 1.000 0.000 0.500 294 79 ' '
_platon_squeeze_void_probe_radius 1.20
_platon_squeeze_details          
;
 The unit cell contains solvent molecules which could not be identified
 and were treated as a diffuse contribution to the overall scattering
 with SQUEEZE/PLATON. The refinement with (without) the model treatment
 gives R1 values of 0.0368 (0.0915) thus improving the results in 60%. 
;

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
C1 C 0.26064(17) 0.5798(3) 0.71681(10) 0.0610(5) Uani 1 1 d . . . . .
H1 H 0.2988 0.6426 0.7122 0.073 Uiso 1 1 calc R U . . .
C2 C 0.1869(2) 0.5019(3) 0.66523(11) 0.0758(7) Uani 1 1 d . . . . .
H2 H 0.1743 0.5110 0.6257 0.091 Uiso 1 1 calc R U . . .
C3 C 0.1323(2) 0.4119(3) 0.67177(11) 0.0783(7) Uani 1 1 d . . . . .
H3 H 0.0814 0.3569 0.6367 0.094 Uiso 1 1 calc R U . . .
C4 C 0.15114(17) 0.4006(3) 0.72968(10) 0.0623(6) Uani 1 1 d . . . . .
H4 H 0.1131 0.3390 0.7348 0.075 Uiso 1 1 calc R U . . .
C5 C 0.22632(13) 0.4809(2) 0.77979(8) 0.0433(4) Uani 1 1 d . . . . .
C6 C 0.25486(12) 0.47928(19) 0.84460(8) 0.0385(3) Uani 1 1 d . . . . .
C7 C 0.21414(13) 0.3962(2) 0.86549(9) 0.0424(4) Uani 1 1 d . . . . .
H7 H 0.1625 0.3312 0.8374 0.051 Uiso 1 1 calc R U . . .
C8 C 0.24918(13) 0.40837(19) 0.92808(9) 0.0412(4) Uani 1 1 d . . . . .
C9 C 0.32693(12) 0.50189(19) 0.96823(8) 0.0400(4) Uani 1 1 d . . . . .
H9 H 0.3537 0.5103 1.0114 0.048 Uiso 1 1 calc R U . . .
C10 C 0.36457(11) 0.58233(18) 0.94446(8) 0.0351(3) Uani 1 1 d . . . . .
C11 C 0.44634(12) 0.68625(18) 0.97988(8) 0.0361(3) Uani 1 1 d . . . . .
C12 C 0.50055(14) 0.7139(2) 1.04391(9) 0.0450(4) Uani 1 1 d . . . . .
H12 H 0.4862 0.6659 1.0684 0.054 Uiso 1 1 calc R U . . .
C13 C 0.57608(15) 0.8127(2) 1.07159(10) 0.0509(4) Uani 1 1 d . . . . .
H13 H 0.6136 0.8344 1.1153 0.061 Uiso 1 1 calc R U . . .
C14 C 0.59615(14) 0.8791(2) 1.03511(10) 0.0506(4) Uani 1 1 d . . . . .
H14 H 0.6477 0.9471 1.0533 0.061 Uiso 1 1 calc R U . . .
C15 C 0.54039(13) 0.8453(2) 0.97186(9) 0.0449(4) Uani 1 1 d . . . . .
H15 H 0.5550 0.8903 0.9469 0.054 Uiso 1 1 calc R U . . .
C16 C 0.20067(18) 0.3268(3) 0.95006(14) 0.0453(15) Uani 0.658(5) 1 d G . P A 1
C17 C 0.24905(17) 0.3063(4) 1.01422(13) 0.0633(12) Uani 0.658(5) 1 d G . P A 1
H17 H 0.3124 0.3421 1.0437 0.076 Uiso 0.658(5) 1 calc R U P A 1
C18 C 0.2047(3) 0.2333(5) 1.03517(12) 0.0765(16) Uani 0.658(5) 1 d G . P A 1
H18 H 0.2378 0.2192 1.0790 0.092 Uiso 0.658(5) 1 calc R U P A 1
C19 C 0.1120(3) 0.1808(5) 0.99197(16) 0.095(2) Uani 0.658(5) 1 d G . P A 1
H19 H 0.0817 0.1309 1.0063 0.114 Uiso 0.658(5) 1 calc R U P A 1
C20 C 0.06364(19) 0.2013(4) 0.92782(15) 0.0853(15) Uani 0.658(5) 1 d G . P A 1
H20 H 0.0003 0.1655 0.8983 0.102 Uiso 0.658(5) 1 calc R U P A 1
C21 C 0.10797(19) 0.2743(3) 0.90686(11) 0.0619(10) Uani 0.658(5) 1 d G . P A 1
H21 H 0.0749 0.2884 0.8630 0.074 Uiso 0.658(5) 1 calc R U P A 1
C31 C 0.51475(13) 0.6426(2) 0.84255(8) 0.0398(4) Uani 1 1 d . . . . .
C32 C 0.56539(12) 0.64704(19) 0.81457(8) 0.0377(3) Uani 1 1 d . . . . .
C33 C 0.55246(16) 0.7637(2) 0.77667(10) 0.0531(5) Uani 1 1 d . . . . .
H33 H 0.5158 0.8473 0.7716 0.064 Uiso 1 1 calc R U . . .
C34 C 0.59230(17) 0.7602(2) 0.74607(11) 0.0567(5) Uani 1 1 d . . . . .
H34 H 0.5830 0.8410 0.7202 0.068 Uiso 1 1 calc R U . . .
C35 C 0.64555(13) 0.6392(2) 0.75326(9) 0.0443(4) Uani 1 1 d . . . . .
C36 C 0.66167(14) 0.5246(2) 0.79229(9) 0.0472(4) Uani 1 1 d . . . . .
H36 H 0.7001 0.4427 0.7984 0.057 Uiso 1 1 calc R U . . .
C37 C 0.62148(14) 0.5292(2) 0.82294(9) 0.0453(4) Uani 1 1 d . . . . .
H37 H 0.6329 0.4499 0.8500 0.054 Uiso 1 1 calc R U . . .
C41 C 0.21245(12) 0.89615(19) 0.81244(9) 0.0410(4) Uani 1 1 d . . . . .
C42 C 0.12355(12) 0.97700(19) 0.76049(9) 0.0401(4) Uani 1 1 d . . . . .
C43 C 0.06324(12) 1.0397(2) 0.77098(9) 0.0426(4) Uani 1 1 d . . . . .
H43 H 0.0763 1.0252 0.8105 0.051 Uiso 1 1 calc R U . . .
C44 C -0.01528(13) 1.1227(2) 0.72511(9) 0.0450(4) Uani 1 1 d . . . . .
H44 H -0.0544 1.1672 0.7337 0.054 Uiso 1 1 calc R U . . .
C45 C -0.03704(13) 1.1410(2) 0.66619(9) 0.0479(4) Uani 1 1 d . . . . .
C46 C 0.02019(15) 1.0732(3) 0.65418(10) 0.0573(5) Uani 1 1 d . . . . .
H46 H 0.0043 1.0810 0.6136 0.069 Uiso 1 1 calc R U . . .
C47 C 0.10017(14) 0.9945(2) 0.70112(9) 0.0516(5) Uani 1 1 d . . . . .
H47 H 0.1400 0.9514 0.6928 0.062 Uiso 1 1 calc R U . . .
Cu1 Cu 0.37991(2) 0.69078(2) 0.85230(2) 0.04023(8) Uani 1 1 d . . . . .
N1 N 0.32785(10) 0.56997(15) 0.88385(6) 0.0367(3) Uani 1 1 d . . . . .
N2 N 0.46675(10) 0.75197(16) 0.94436(7) 0.0379(3) Uani 1 1 d . . . . .
N3 N 0.28029(11) 0.56971(18) 0.77326(7) 0.0460(3) Uani 1 1 d . . . . .
O1 O 0.45607(10) 0.74902(16) 0.82726(6) 0.0480(3) Uani 1 1 d . . . . .
O2 O 0.52706(10) 0.53771(15) 0.87651(7) 0.0527(3) Uani 1 1 d . . . . .
O3 O 0.27725(9) 0.88150(15) 0.80619(7) 0.0498(3) Uani 1 1 d . . . . .
O4 O 0.22012(10) 0.85057(16) 0.85899(7) 0.0531(3) Uani 1 1 d . . . . .
O5 O 0.68057(11) 0.63921(18) 0.72045(7) 0.0607(4) Uani 1 1 d . . . . .
H5E H 0.6911 0.5535 0.7161 0.073 Uiso 1 1 d R U . . .
O6 O -0.11029(11) 1.22382(19) 0.61987(7) 0.0648(4) Uani 1 1 d . . . . .
H6E H -0.1459 1.2684 0.6260 0.078 Uiso 1 1 d R U . . .
C16B C 0.2143(4) 0.3160(6) 0.9547(3) 0.050(3) Uani 0.342(5) 1 d G . P A 2
C17B C 0.2162(5) 0.3710(6) 1.0035(3) 0.067(2) Uani 0.342(5) 1 d G . P A 2
H17B H 0.2443 0.4649 1.0216 0.081 Uiso 0.342(5) 1 calc R U P A 2
C18B C 0.1768(6) 0.2886(8) 1.0259(3) 0.091(4) Uani 0.342(5) 1 d G . P A 2
H18B H 0.1781 0.3262 1.0592 0.110 Uiso 0.342(5) 1 calc R U P A 2
C19B C 0.1356(6) 0.1512(8) 0.9994(3) 0.084(4) Uani 0.342(5) 1 d G . P A 2
H19B H 0.1087 0.0949 1.0146 0.101 Uiso 0.342(5) 1 calc R U P A 2
C21B C 0.1338(5) 0.0962(6) 0.9506(3) 0.095(4) Uani 0.342(5) 1 d G . P A 2
H21B H 0.1056 0.0023 0.9325 0.114 Uiso 0.342(5) 1 calc R U P A 2
C20B C 0.1731(5) 0.1786(6) 0.9282(3) 0.070(2) Uani 0.342(5) 1 d G . P A 2
H20B H 0.1719 0.1410 0.8949 0.084 Uiso 0.342(5) 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N3 1.340(2) . ?
C1 C2 1.377(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.360(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.386(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(3) . ?
C4 H4 0.9500 . ?
C5 N3 1.345(2) . ?
C5 C6 1.490(2) . ?
C6 N1 1.334(2) . ?
C6 C7 1.383(2) . ?
C7 C8 1.398(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.396(3) . ?
C8 C16B 1.466(4) . ?
C8 C16 1.509(3) . ?
C9 C10 1.386(2) . ?
C9 H9 0.9500 . ?
C10 N1 1.340(2) . ?
C10 C11 1.481(2) . ?
C11 N2 1.355(2) . ?
C11 C12 1.385(2) . ?
C12 C13 1.386(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.376(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.378(3) . ?
C14 H14 0.9500 . ?
C15 N2 1.333(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.3900 . ?
C16 C21 1.3900 . ?
C17 C18 1.3900 . ?
C17 H17 0.9500 . ?
C18 C19 1.3900 . ?
C18 H18 0.9500 . ?
C19 C20 1.3900 . ?
C19 H19 0.9500 . ?
C20 C21 1.3900 . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C31 O2 1.238(2) . ?
C31 O1 1.285(2) . ?
C31 C32 1.495(2) . ?
C31 Cu1 2.6132(17) . ?
C32 C37 1.378(2) . ?
C32 C33 1.383(3) . ?
C33 C34 1.384(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.379(3) . ?
C34 H34 0.9500 . ?
C35 O5 1.364(2) . ?
C35 C36 1.372(3) . ?
C36 C37 1.392(2) . ?
C36 H36 0.9500 . ?
C37 H37 0.9500 . ?
C41 O4 1.247(2) . ?
C41 O3 1.274(2) . ?
C41 C42 1.504(2) . ?
C42 C43 1.391(2) . ?
C42 C47 1.394(3) . ?
C43 C44 1.381(3) . ?
C43 H43 0.9500 . ?
C44 C45 1.395(3) . ?
C44 H44 0.9500 . ?
C45 O6 1.344(2) . ?
C45 C46 1.390(3) . ?
C46 C47 1.381(3) . ?
C46 H46 0.9500 . ?
C47 H47 0.9500 . ?
Cu1 O1 1.9276(12) . ?
Cu1 N1 1.9370(14) . ?
Cu1 N2 2.0301(15) . ?
Cu1 N3 2.0522(16) . ?
Cu1 O3 2.2434(13) . ?
Cu1 O2 2.6635(14) . ?
O5 H5E 0.8199 . ?
O6 H6E 0.8497 . ?
C16B C17B 1.3900 . ?
C16B C20B 1.3900 . ?
C17B C18B 1.3900 . ?
C17B H17B 0.9500 . ?
C18B C19B 1.3900 . ?
C18B H18B 0.9500 . ?
C19B C21B 1.3900 . ?
C19B H19B 0.9500 . ?
C21B C20B 1.3900 . ?
C21B H21B 0.9500 . ?
C20B H20B 0.9500 . ?

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
N3 C1 C2 122.1(2) . . ?
N3 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C3 C2 C1 119.0(2) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 119.8(2) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 118.6(2) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
N3 C5 C4 121.51(18) . . ?
N3 C5 C6 114.07(16) . . ?
C4 C5 C6 124.42(18) . . ?
N1 C6 C7 120.51(15) . . ?
N1 C6 C5 112.58(15) . . ?
C7 C6 C5 126.91(16) . . ?
C6 C7 C8 119.78(16) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C7 C8 C9 118.23(16) . . ?
C7 C8 C16B 122.8(3) . . ?
C9 C8 C16B 118.7(3) . . ?
C7 C8 C16 120.13(19) . . ?
C9 C8 C16 121.59(18) . . ?
C10 C9 C8 119.25(16) . . ?
C10 C9 H9 120.4 . . ?
C8 C9 H9 120.4 . . ?
N1 C10 C9 120.80(16) . . ?
N1 C10 C11 112.55(14) . . ?
C9 C10 C11 126.65(15) . . ?
N2 C11 C12 121.33(16) . . ?
N2 C11 C10 114.04(14) . . ?
C12 C11 C10 124.60(15) . . ?
C13 C12 C11 118.92(17) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C14 C13 C12 119.31(18) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C15 C14 C13 118.97(18) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
N2 C15 C14 122.47(17) . . ?
N2 C15 H15 118.8 . . ?
C14 C15 H15 118.8 . . ?
C17 C16 C21 120.0 . . ?
C17 C16 C8 119.4(2) . . ?
C21 C16 C8 120.61(19) . . ?
C18 C17 C16 120.0 . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.0 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 H18 120.0 . . ?
C20 C19 C18 120.0 . . ?
C20 C19 H19 120.0 . . ?
C18 C19 H19 120.0 . . ?
C21 C20 C19 120.0 . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C16 120.0 . . ?
C20 C21 H21 120.0 . . ?
C16 C21 H21 120.0 . . ?
O2 C31 O1 122.88(15) . . ?
O2 C31 C32 120.64(16) . . ?
O1 C31 C32 116.42(15) . . ?
O2 C31 Cu1 78.70(10) . . ?
C32 C31 Cu1 158.23(13) . . ?
C37 C32 C33 118.57(15) . . ?
C37 C32 C31 120.08(16) . . ?
C33 C32 C31 121.22(16) . . ?
C34 C33 C32 120.83(18) . . ?
C34 C33 H33 119.6 . . ?
C32 C33 H33 119.6 . . ?
C35 C34 C33 119.84(18) . . ?
C35 C34 H34 120.1 . . ?
C33 C34 H34 120.1 . . ?
O5 C35 C36 122.48(17) . . ?
O5 C35 C34 117.44(17) . . ?
C36 C35 C34 120.07(16) . . ?
C35 C36 C37 119.67(17) . . ?
C35 C36 H36 120.2 . . ?
C37 C36 H36 120.2 . . ?
C32 C37 C36 120.95(17) . . ?
C32 C37 H37 119.5 . . ?
C36 C37 H37 119.5 . . ?
O4 C41 O3 123.83(17) . . ?
O4 C41 C42 119.66(15) . . ?
O3 C41 C42 116.49(16) . . ?
C43 C42 C47 118.04(17) . . ?
C43 C42 C41 120.57(16) . . ?
C47 C42 C41 121.37(15) . . ?
C44 C43 C42 121.33(17) . . ?
C44 C43 H43 119.3 . . ?
C42 C43 H43 119.3 . . ?
C43 C44 C45 119.96(16) . . ?
C43 C44 H44 120.0 . . ?
C45 C44 H44 120.0 . . ?
O6 C45 C46 117.27(18) . . ?
O6 C45 C44 123.50(17) . . ?
C46 C45 C44 119.22(18) . . ?
C47 C46 C45 120.14(18) . . ?
C47 C46 H46 119.9 . . ?
C45 C46 H46 119.9 . . ?
C46 C47 C42 121.21(17) . . ?
C46 C47 H47 119.4 . . ?
C42 C47 H47 119.4 . . ?
O1 Cu1 N1 160.24(6) . . ?
O1 Cu1 N2 100.77(6) . . ?
N1 Cu1 N2 79.84(6) . . ?
O1 Cu1 N3 97.13(6) . . ?
N1 Cu1 N3 79.46(6) . . ?
N2 Cu1 N3 158.77(6) . . ?
O1 Cu1 O3 96.16(5) . . ?
N1 Cu1 O3 103.02(5) . . ?
N2 Cu1 O3 102.38(6) . . ?
N3 Cu1 O3 86.85(6) . . ?
O1 Cu1 C31 28.01(6) . . ?
N1 Cu1 C31 132.30(6) . . ?
N2 Cu1 C31 96.68(5) . . ?
N3 Cu1 C31 93.76(6) . . ?
O3 Cu1 C31 123.87(5) . . ?
O1 Cu1 O2 54.94(5) . . ?
N1 Cu1 O2 105.62(5) . . ?
N2 Cu1 O2 87.16(5) . . ?
N3 Cu1 O2 93.90(5) . . ?
O3 Cu1 O2 151.00(4) . . ?
C31 Cu1 O2 27.12(5) . . ?
C6 N1 C10 121.40(14) . . ?
C6 N1 Cu1 119.49(11) . . ?
C10 N1 Cu1 119.08(11) . . ?
C15 N2 C11 118.99(16) . . ?
C15 N2 Cu1 126.58(12) . . ?
C11 N2 Cu1 114.41(11) . . ?
C1 N3 C5 119.03(18) . . ?
C1 N3 Cu1 126.63(15) . . ?
C5 N3 Cu1 114.14(12) . . ?
C31 O1 Cu1 107.18(11) . . ?
C31 O2 Cu1 74.17(10) . . ?
C41 O3 Cu1 120.11(11) . . ?
C35 O5 H5E 109.3 . . ?
C45 O6 H6E 119.6 . . ?
C17B C16B C20B 120.0 . . ?
C17B C16B C8 119.7(3) . . ?
C20B C16B C8 120.2(3) . . ?
C16B C17B C18B 120.0 . . ?
C16B C17B H17B 120.0 . . ?
C18B C17B H17B 120.0 . . ?
C17B C18B C19B 120.0 . . ?
C17B C18B H18B 120.0 . . ?
C19B C18B H18B 120.0 . . ?
C21B C19B C18B 120.0 . . ?
C21B C19B H19B 120.0 . . ?
C18B C19B H19B 120.0 . . ?
C19B C21B C20B 120.0 . . ?
C19B C21B H21B 120.0 . . ?
C20B C21B H21B 120.0 . . ?
C21B C20B C16B 120.0 . . ?
C21B C20B H20B 120.0 . . ?
C16B C20B H20B 120.0 . . ?

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
O5 H5E O3 0.82 1.87 2.672(2) 165.3 2_646
O6 H6E O4 0.85 1.77 2.6177(19) 176.3 2_556
C9 H9 O2 0.95 2.43 3.314(2) 154.4 3_667
C12 H12 O2 0.95 2.46 3.363(2) 158.2 3_667
O5 H5E O3 0.82 1.87 2.672(2) 165.3 2_646
O6 H6E O4 0.85 1.77 2.6177(19) 176.3 2_556
C9 H9 O2 0.95 2.43 3.314(2) 154.4 3_667
C12 H12 O2 0.95 2.46 3.363(2) 158.2 3_667
O5 H5E O3 0.82 1.87 2.672(2) 165.3 2_646
O6 H6E O4 0.85 1.77 2.6177(19) 176.3 2_556
C9 H9 O2 0.95 2.43 3.314(2) 154.4 3_667
C12 H12 O2 0.95 2.46 3.363(2) 158.2 3_667

_refine_diff_density_max         0.307
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.047



####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 941489'
_audit_update_record             
;
2016-01-27 deposited with the CCDC.
2016-02-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C35 H25 Cu N3 O6, C H4 O'
_chemical_formula_sum            'C36 H29 Cu N3 O7'
_chemical_formula_weight         678.94

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.3200 1.2650 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0848(3)
_cell_length_b                   12.0013(4)
_cell_length_c                   15.5065(5)
_cell_angle_alpha                94.097(2)
_cell_angle_beta                 104.306(3)
_cell_angle_gamma                107.188(2)
_cell_volume                     1545.90(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_F_000             702
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.763
_shelx_estimated_absorpt_T_min   0.838
_shelx_estimated_absorpt_T_max   0.934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.888
_exptl_absorpt_correction_T_max  0.934
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16450
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.038
_diffrn_reflns_theta_max         28.298
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.980
_reflns_number_total             7458
_reflns_number_gt                6215
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1999)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'


_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0371P)²+0.8584P] 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         7458
_refine_ls_number_parameters     434
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_ref         0.0822
_refine_ls_wR_factor_gt          0.0766
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 0.500 1.000 53 7 ' '
_platon_squeeze_details          
;
;

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
C1 C 0.9164(2) -0.08357(15) 0.28283(12) 0.0204(3) Uani 1 1 d . . . . .
H1 H 0.8260 -0.1233 0.2329 0.025 Uiso 1 1 calc R U . . .
C2 C 1.0493(2) -0.12261(16) 0.29908(12) 0.0226(4) Uani 1 1 d . . . . .
H2 H 1.0500 -0.1875 0.2605 0.027 Uiso 1 1 calc R U . . .
C3 C 1.1796(2) -0.06546(15) 0.37198(12) 0.0204(3) Uani 1 1 d . . . . .
H3 H 1.2708 -0.0914 0.3849 0.024 Uiso 1 1 calc R U . . .
C4 C 1.1767(2) 0.03039(15) 0.42648(11) 0.0180(3) Uani 1 1 d . . . . .
H4 H 1.2656 0.0712 0.4769 0.022 Uiso 1 1 calc R U . . .
C5 C 1.04119(19) 0.06522(14) 0.40577(11) 0.0147(3) Uani 1 1 d . . . . .
C6 C 1.0229(2) 0.16637(14) 0.45814(11) 0.0150(3) Uani 1 1 d . . . . .
C7 C 1.1348(2) 0.23984(14) 0.53337(11) 0.0166(3) Uani 1 1 d . . . . .
H7 H 1.2367 0.2298 0.5551 0.020 Uiso 1 1 calc R U . . .
C8 C 1.0969(2) 0.32962(14) 0.57747(11) 0.0163(3) Uani 1 1 d . . . . .
C9 C 0.9455(2) 0.34190(14) 0.54136(11) 0.0169(3) Uani 1 1 d . . . . .
H9 H 0.9160 0.4020 0.5690 0.020 Uiso 1 1 calc R U . . .
C10 C 0.8402(2) 0.26593(14) 0.46543(11) 0.0152(3) Uani 1 1 d . . . . .
C11 C 0.6747(2) 0.26475(14) 0.42008(11) 0.0159(3) Uani 1 1 d . . . . .
C12 C 0.6080(2) 0.34717(16) 0.44461(12) 0.0202(3) Uani 1 1 d . . . . .
H12 H 0.6670 0.4093 0.4937 0.024 Uiso 1 1 calc R U . . .
C13 C 0.4528(2) 0.33762(17) 0.39612(13) 0.0241(4) Uani 1 1 d . . . . .
H13 H 0.4044 0.3935 0.4114 0.029 Uiso 1 1 calc R U . . .
C14 C 0.3700(2) 0.24603(17) 0.32565(13) 0.0246(4) Uani 1 1 d . . . . .
H14 H 0.2635 0.2376 0.2921 0.030 Uiso 1 1 calc R U . . .
C15 C 0.4443(2) 0.16651(16) 0.30440(12) 0.0206(4) Uani 1 1 d . . . . .
H15 H 0.3872 0.1036 0.2557 0.025 Uiso 1 1 calc R U . . .
C16 C 1.2094(2) 0.40659(15) 0.66094(11) 0.0176(3) Uani 1 1 d . . . . .
C17 C 1.1963(2) 0.51530(15) 0.68974(12) 0.0199(3) Uani 1 1 d . . . . .
H17 H 1.1131 0.5402 0.6554 0.024 Uiso 1 1 calc R U . . .
C18 C 1.3023(2) 0.58714(16) 0.76722(13) 0.0251(4) Uani 1 1 d . . . . .
H18 H 1.2916 0.6609 0.7857 0.030 Uiso 1 1 calc R U . . .
C19 C 1.4242(2) 0.55206(18) 0.81816(14) 0.0323(5) Uani 1 1 d . . . . .
H19 H 1.4973 0.6017 0.8714 0.039 Uiso 1 1 calc R U . . .
C20 C 1.4390(2) 0.44407(19) 0.79107(14) 0.0341(5) Uani 1 1 d . . . . .
H20 H 1.5221 0.4195 0.8259 0.041 Uiso 1 1 calc R U . . .
C21 C 1.3330(2) 0.37260(17) 0.71358(13) 0.0258(4) Uani 1 1 d . . . . .
H21 H 1.3440 0.2989 0.6956 0.031 Uiso 1 1 calc R U . . .
C22 C 0.9031(2) 0.20225(14) 0.19836(11) 0.0161(3) Uani 1 1 d . . . . .
C23 C 0.9529(2) 0.19000(15) 0.11330(11) 0.0170(3) Uani 1 1 d . . . . .
C24 C 1.0960(2) 0.26607(16) 0.10510(12) 0.0207(3) Uani 1 1 d . . . . .
H24 H 1.1644 0.3270 0.1532 0.025 Uiso 1 1 calc R U . . .
C25 C 1.1377(2) 0.25169(17) 0.02557(13) 0.0257(4) Uani 1 1 d . . . . .
H25 H 1.2348 0.3038 0.0194 0.031 Uiso 1 1 calc R U . . .
C26 C 1.0400(2) 0.16288(18) -0.04466(13) 0.0256(4) Uani 1 1 d . . . . .
H26 H 1.0704 0.1540 -0.0985 0.031 Uiso 1 1 calc R U . . .
C27 C 0.8972(2) 0.08643(16) -0.03654(12) 0.0218(4) Uani 1 1 d . . . . .
C28 C 0.8544(2) 0.10060(15) 0.04252(12) 0.0192(3) Uani 1 1 d . . . . .
H28 H 0.7569 0.0487 0.0483 0.023 Uiso 1 1 calc R U . . .
C29 C 0.5031(2) -0.13004(14) 0.30147(12) 0.0169(3) Uani 1 1 d . . . . .
C30 C 0.3641(2) -0.24119(14) 0.26157(12) 0.0167(3) Uani 1 1 d . . . . .
C31 C 0.3310(2) -0.32711(14) 0.31609(12) 0.0176(3) Uani 1 1 d . . . . .
H31 H 0.3931 -0.3131 0.3772 0.021 Uiso 1 1 calc R U . . .
C32 C 0.2079(2) -0.43308(15) 0.28170(12) 0.0189(3) Uani 1 1 d . . . . .
C33 C 0.1125(2) -0.45112(15) 0.19323(13) 0.0232(4) Uani 1 1 d . . . . .
H33 H 0.0253 -0.5223 0.1698 0.028 Uiso 1 1 calc R U . . .
C34 C 0.1454(2) -0.36476(16) 0.13955(13) 0.0253(4) Uani 1 1 d . . . . .
H34 H 0.0804 -0.3774 0.0791 0.030 Uiso 1 1 calc R U . . .
C35 C 0.2715(2) -0.26034(15) 0.17252(12) 0.0212(4) Uani 1 1 d . . . . .
H35 H 0.2945 -0.2024 0.1348 0.025 Uiso 1 1 calc R U . . .
C36 C 0.5030(3) 0.1756(2) 0.00103(15) 0.0359(5) Uani 1 1 d . . . . .
H36A H 0.4108 0.1984 -0.0297 0.054 Uiso 1 1 calc R U . . .
H36B H 0.5163 0.1149 -0.0393 0.054 Uiso 1 1 calc R U . . .
H36C H 0.6002 0.2449 0.0176 0.054 Uiso 1 1 calc R U . . .
Cu1 Cu 0.72564(2) 0.07521(2) 0.32013(2) 0.01502(6) Uani 1 1 d . . . . .
N1 N 0.91219(17) 0.00823(12) 0.33539(9) 0.0165(3) Uani 1 1 d . . . . .
N2 N 0.87954(16) 0.18080(12) 0.42533(9) 0.0146(3) Uani 1 1 d . . . . .
N3 N 0.59412(17) 0.17550(12) 0.35036(9) 0.0167(3) Uani 1 1 d . . . . .
O1 O 0.76276(14) 0.13906(11) 0.19683(8) 0.0189(2) Uani 1 1 d . . . . .
O2 O 1.00109(15) 0.27097(10) 0.26630(8) 0.0214(3) Uani 1 1 d . . . . .
O3 O 0.54775(15) -0.06031(10) 0.24735(8) 0.0201(3) Uani 1 1 d . . . . .
O4 O 0.57006(16) -0.11101(11) 0.38352(9) 0.0270(3) Uani 1 1 d . . . . .
O5 O 0.80402(17) 0.00066(13) -0.10732(9) 0.0282(3) Uani 1 1 d D . . . .
O6 O 0.18606(15) -0.51525(11) 0.33796(9) 0.0225(3) Uani 1 1 d D . . . .
O7 O 0.47655(17) 0.13033(15) 0.07976(10) 0.0365(4) Uani 1 1 d D . . . .
H5O H 0.715(3) -0.044(2) -0.0946(18) 0.055 Uiso 1 1 d D U . . .
H6O H 0.119(3) -0.5833(18) 0.3050(17) 0.055 Uiso 1 1 d D U . . .
H7O H 0.566(3) 0.121(2) 0.1138(17) 0.055 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
C1 N1 1.338(2) . ?
C1 C2 1.393(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.378(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.386(2) . ?
C4 H4 0.9500 . ?
C5 N1 1.349(2) . ?
C5 C6 1.485(2) . ?
C6 N2 1.343(2) . ?
C6 C7 1.382(2) . ?
C7 C8 1.406(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.406(2) . ?
C8 C16 1.480(2) . ?
C9 C10 1.381(2) . ?
C9 H9 0.9500 . ?
C10 N2 1.339(2) . ?
C10 C11 1.490(2) . ?
C11 N3 1.354(2) . ?
C11 C12 1.380(2) . ?
C12 C13 1.391(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.379(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(3) . ?
C14 H14 0.9500 . ?
C15 N3 1.340(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.396(2) . ?
C16 C21 1.400(2) . ?
C17 C18 1.380(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.385(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.388(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.378(3) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 O2 1.249(2) . ?
C22 O1 1.270(2) . ?
C22 C23 1.508(2) . ?
C23 C28 1.391(2) . ?
C23 C24 1.391(2) . ?
C24 C25 1.390(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.381(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.391(3) . ?
C26 H26 0.9500 . ?
C27 O5 1.358(2) . ?
C27 C28 1.389(3) . ?
C28 H28 0.9500 . ?
C29 O4 1.239(2) . ?
C29 O3 1.279(2) . ?
C29 C30 1.503(2) . ?
C29 Cu1 2.6275(17) . ?
C30 C35 1.391(2) . ?
C30 C31 1.391(2) . ?
C31 C32 1.386(2) . ?
C31 H31 0.9500 . ?
C32 O6 1.366(2) . ?
C32 C33 1.393(3) . ?
C33 C34 1.386(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.384(2) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
C36 O7 1.416(3) . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
Cu1 N2 1.9370(14) . ?
Cu1 O3 1.9528(12) . ?
Cu1 N3 2.0353(14) . ?
Cu1 N1 2.0515(14) . ?
Cu1 O1 2.1753(12) . ?
Cu1 O4 2.6632(13) . ?
O5 H5O 0.906(17) . ?
O6 H6O 0.889(17) . ?
O7 H7O 0.894(17) . ?

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 C1 C2 122.01(16) . . ?
N1 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C3 C2 C1 118.86(16) . . ?
C3 C2 H2 120.6 . . ?
C1 C2 H2 120.6 . . ?
C2 C3 C4 119.48(16) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 118.56(16) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
N1 C5 C4 122.15(15) . . ?
N1 C5 C6 113.84(14) . . ?
C4 C5 C6 124.00(15) . . ?
N2 C6 C7 121.06(15) . . ?
N2 C6 C5 112.52(14) . . ?
C7 C6 C5 126.41(15) . . ?
C6 C7 C8 119.54(15) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C7 C8 C9 117.82(15) . . ?
C7 C8 C16 121.59(15) . . ?
C9 C8 C16 120.56(15) . . ?
C10 C9 C8 119.48(15) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
N2 C10 C9 121.25(15) . . ?
N2 C10 C11 112.37(14) . . ?
C9 C10 C11 126.37(15) . . ?
N3 C11 C12 122.12(15) . . ?
N3 C11 C10 113.77(14) . . ?
C12 C11 C10 124.10(15) . . ?
C11 C12 C13 118.72(17) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?
C14 C13 C12 119.24(17) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C15 119.07(16) . . ?
C13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
N3 C15 C14 122.09(17) . . ?
N3 C15 H15 119.0 . . ?
C14 C15 H15 119.0 . . ?
C17 C16 C21 117.78(16) . . ?
C17 C16 C8 121.37(15) . . ?
C21 C16 C8 120.85(15) . . ?
C18 C17 C16 121.13(16) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C19 120.17(17) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C20 119.72(17) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C21 C20 C19 119.93(18) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C16 121.27(17) . . ?
C20 C21 H21 119.4 . . ?
C16 C21 H21 119.4 . . ?
O2 C22 O1 123.68(16) . . ?
O2 C22 C23 119.17(15) . . ?
O1 C22 C23 117.13(15) . . ?
C28 C23 C24 119.86(16) . . ?
C28 C23 C22 119.19(15) . . ?
C24 C23 C22 120.95(15) . . ?
C25 C24 C23 119.15(17) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
C26 C25 C24 121.01(17) . . ?
C26 C25 H25 119.5 . . ?
C24 C25 H25 119.5 . . ?
C25 C26 C27 119.97(17) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
O5 C27 C28 122.46(17) . . ?
O5 C27 C26 118.18(17) . . ?
C28 C27 C26 119.35(17) . . ?
C27 C28 C23 120.66(17) . . ?
C27 C28 H28 119.7 . . ?
C23 C28 H28 119.7 . . ?
O4 C29 O3 123.36(16) . . ?
O4 C29 C30 119.38(16) . . ?
O3 C29 C30 117.25(15) . . ?
O4 C29 Cu1 78.06(10) . . ?
O3 C29 Cu1 45.32(8) . . ?
C30 C29 Cu1 162.54(12) . . ?
C35 C30 C31 120.06(16) . . ?
C35 C30 C29 121.92(16) . . ?
C31 C30 C29 118.02(15) . . ?
C32 C31 C30 120.37(16) . . ?
C32 C31 H31 119.8 . . ?
C30 C31 H31 119.8 . . ?
O6 C32 C31 117.26(16) . . ?
O6 C32 C33 123.15(15) . . ?
C31 C32 C33 119.59(16) . . ?
C34 C33 C32 119.65(16) . . ?
C34 C33 H33 120.2 . . ?
C32 C33 H33 120.2 . . ?
C35 C34 C33 121.06(17) . . ?
C35 C34 H34 119.5 . . ?
C33 C34 H34 119.5 . . ?
C34 C35 C30 119.21(17) . . ?
C34 C35 H35 120.4 . . ?
C30 C35 H35 120.4 . . ?
O7 C36 H36A 109.5 . . ?
O7 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
O7 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
N2 Cu1 O3 159.86(5) . . ?
N2 Cu1 N3 79.68(6) . . ?
O3 Cu1 N3 97.95(5) . . ?
N2 Cu1 N1 79.24(6) . . ?
O3 Cu1 N1 100.62(5) . . ?
N3 Cu1 N1 158.63(6) . . ?
N2 Cu1 O1 111.01(5) . . ?
O3 Cu1 O1 89.13(5) . . ?
N3 Cu1 O1 98.98(5) . . ?
N1 Cu1 O1 91.83(5) . . ?
N2 Cu1 C29 132.17(6) . . ?
O3 Cu1 C29 27.76(5) . . ?
N3 Cu1 C29 96.22(5) . . ?
N1 Cu1 C29 95.28(5) . . ?
O1 Cu1 C29 116.66(5) . . ?
N2 Cu1 O4 105.18(5) . . ?
O3 Cu1 O4 54.83(4) . . ?
N3 Cu1 O4 94.04(5) . . ?
N1 Cu1 O4 88.09(5) . . ?
O1 Cu1 O4 143.13(4) . . ?
C29 Cu1 O4 27.07(5) . . ?
C1 N1 C5 118.92(14) . . ?
C1 N1 Cu1 126.39(12) . . ?
C5 N1 Cu1 114.69(10) . . ?
C10 N2 C6 120.85(14) . . ?
C10 N2 Cu1 119.44(11) . . ?
C6 N2 Cu1 119.70(11) . . ?
C15 N3 C11 118.76(15) . . ?
C15 N3 Cu1 126.46(12) . . ?
C11 N3 Cu1 114.57(11) . . ?
C22 O1 Cu1 118.17(10) . . ?
C29 O3 Cu1 106.91(10) . . ?
C29 O4 Cu1 74.86(10) . . ?
C27 O5 H5O 110.8(18) . . ?
C32 O6 H6O 108.1(18) . . ?
C36 O7 H7O 110.9(18) . . ?

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
C4 H4 O4 0.95 2.23 3.136(2) 159.0 2_756
C7 H7 O4 0.95 2.62 3.502(2) 154.6 2_756
C9 H9 O6 0.95 2.43 3.358(2) 164.9 2_656
C12 H12 O6 0.95 2.65 3.552(2) 159.0 2_656
C14 H14 O2 0.95 2.47 3.358(2) 154.8 1_455
C15 H15 O5 0.95 2.49 3.391(2) 157.9 2_655
O5 H5O O7 0.906(17) 1.821(17) 2.723(2) 174(3) 2_655
O6 H6O O2 0.889(17) 1.730(18) 2.6006(17) 166(3) 1_445
O7 H7O O1 0.894(17) 1.871(18) 2.7471(19) 166(3) .
C4 H4 O4 0.95 2.23 3.136(2) 159.0 2_756
C7 H7 O4 0.95 2.62 3.502(2) 154.6 2_756
C9 H9 O6 0.95 2.43 3.358(2) 164.9 2_656
C12 H12 O6 0.95 2.65 3.552(2) 159.0 2_656
C14 H14 O2 0.95 2.47 3.358(2) 154.8 1_455
C15 H15 O5 0.95 2.49 3.391(2) 157.9 2_655
O5 H5O O7 0.906(17) 1.821(17) 2.723(2) 174(3) 2_655
O6 H6O O2 0.889(17) 1.730(18) 2.6006(17) 166(3) 1_445
O7 H7O O1 0.894(17) 1.871(18) 2.7471(19) 166(3) .

_refine_diff_density_max         0.405
_refine_diff_density_min         -0.470
_refine_diff_density_rms         0.060

_shelxl_version_number           2014-3

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

data_3
_database_code_depnum_ccdc_archive 'CCDC 941490'
_audit_update_record             
;
2016-01-27 deposited with the CCDC.
2016-02-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C35 H25 Cu N3 O6'
_chemical_formula_sum            'C35 H25 Cu N3 O6'
_chemical_formula_weight         646.93


loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.3200 1.2650 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5127(5)
_cell_length_b                   10.7981(6)
_cell_length_c                   15.2472(9)
_cell_angle_alpha                97.794(3)
_cell_angle_beta                 90.711(4)
_cell_angle_gamma                113.681(3)
_cell_volume                     1417.18(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.516
_exptl_crystal_F_000             666
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.826
_shelx_estimated_absorpt_T_min   0.833
_shelx_estimated_absorpt_T_max   0.915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.827
_exptl_absorpt_correction_T_max  0.913
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22686
_diffrn_reflns_av_unetI/netI     0.0185
_diffrn_reflns_av_R_equivalents  0.0167
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.084
_diffrn_reflns_theta_max         28.357
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7037
_reflns_number_gt                6230
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Giacovazzo et al, 1999)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0743P)²+0.6453P] 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         7037
_refine_ls_number_parameters     414
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.1180
_refine_ls_wR_factor_gt          0.1148
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_restrained_S_all      1.014
_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
C1 C 1.0519(2) 0.5021(2) 0.21349(13) 0.0389(4) Uani 1 1 d . . . . .
H1 H 1.0114 0.5250 0.2653 0.047 Uiso 1 1 calc R U . . .
C2 C 1.2104(2) 0.5530(2) 0.20986(14) 0.0438(5) Uani 1 1 d . . . . .
H2 H 1.2751 0.6082 0.2589 0.053 Uiso 1 1 calc R U . . .
C3 C 1.2704(2) 0.5212(2) 0.13335(15) 0.0413(4) Uani 1 1 d . . . . .
H3 H 1.3764 0.5558 0.1296 0.050 Uiso 1 1 calc R U . . .
C4 C 1.1715(2) 0.4365(2) 0.06087(13) 0.0348(4) Uani 1 1 d . . . . .
H4 H 1.2102 0.4143 0.0081 0.042 Uiso 1 1 calc R U . . .
C5 C 1.0149(2) 0.38648(17) 0.06956(11) 0.0297(3) Uani 1 1 d . . . . .
C6 C 0.89667(19) 0.29242(17) -0.00088(11) 0.0283(3) Uani 1 1 d . . . . .
C7 C 0.9224(2) 0.24051(19) -0.08479(12) 0.0312(3) Uani 1 1 d . . . . .
H7 H 1.0223 0.2621 -0.1012 0.037 Uiso 1 1 calc R U . . .
C8 C 0.7968(2) 0.15545(18) -0.14449(11) 0.0309(3) Uani 1 1 d . . . . .
C9 C 0.6482(2) 0.12673(18) -0.11666(12) 0.0321(4) Uani 1 1 d . . . . .
H9 H 0.5622 0.0716 -0.1548 0.038 Uiso 1 1 calc R U . . .
C10 C 0.63083(19) 0.18110(17) -0.03218(12) 0.0288(3) Uani 1 1 d . . . . .
C11 C 0.4832(2) 0.16487(18) 0.00566(12) 0.0303(3) Uani 1 1 d . . . . .
C12 C 0.3415(2) 0.0887(2) -0.03983(14) 0.0381(4) Uani 1 1 d . . . . .
H12 H 0.3339 0.0420 -0.0968 0.046 Uiso 1 1 calc R U . . .
C13 C 0.2105(2) 0.0835(2) 0.00173(17) 0.0465(5) Uani 1 1 d . . . . .
H13 H 0.1137 0.0343 -0.0277 0.056 Uiso 1 1 calc R U . . .
C14 C 0.2249(2) 0.1516(2) 0.08664(17) 0.0461(5) Uani 1 1 d . . . . .
H14 H 0.1382 0.1482 0.1155 0.055 Uiso 1 1 calc R U . . .
C15 C 0.3708(2) 0.2252(2) 0.12834(14) 0.0402(4) Uani 1 1 d . . . . .
H15 H 0.3806 0.2709 0.1858 0.048 Uiso 1 1 calc R U . . .
C16 C 0.8167(2) 0.1010(2) -0.23575(12) 0.0352(4) Uani 1 1 d . . . . .
C17 C 0.6928(3) -0.0010(3) -0.28811(15) 0.0524(6) Uani 1 1 d . . . . .
H17 H 0.5977 -0.0384 -0.2646 0.063 Uiso 1 1 calc R U . . .
C18 C 0.7098(3) -0.0477(3) -0.37512(17) 0.0677(8) Uani 1 1 d . . . . .
H18 H 0.6259 -0.1154 -0.4096 0.081 Uiso 1 1 calc R U . . .
C19 C 0.8500(4) 0.0060(3) -0.41034(17) 0.0635(7) Uani 1 1 d . . . . .
H19 H 0.8609 -0.0233 -0.4691 0.076 Uiso 1 1 calc R U . . .
C20 C 0.9727(4) 0.1023(4) -0.35865(19) 0.0747(9) Uani 1 1 d . . . . .
H20 H 1.0684 0.1371 -0.3819 0.090 Uiso 1 1 calc R U . . .
C21 C 0.9571(3) 0.1492(3) -0.27209(17) 0.0628(7) Uani 1 1 d . . . . .
H21 H 1.0428 0.2145 -0.2377 0.075 Uiso 1 1 calc R U . . .
C31 C 0.8401(2) 0.1685(2) 0.23626(15) 0.0406(4) Uani 1 1 d . . . . .
C32 C 0.9107(2) 0.2282(2) 0.32863(15) 0.0431(4) Uani 1 1 d . . . . .
C33 C 1.0669(3) 0.2598(3) 0.34770(19) 0.0583(6) Uani 1 1 d . . . . .
H33 H 1.1241 0.2394 0.3034 0.070 Uiso 1 1 calc R U . . .
C34 C 1.1374(4) 0.3212(4) 0.4319(2) 0.0765(9) Uani 1 1 d . . . . .
H34 H 1.2419 0.3444 0.4436 0.092 Uiso 1 1 calc R U . . .
C35 C 1.0511(5) 0.3473(4) 0.4978(2) 0.0840(10) Uani 1 1 d . . . . .
H35 H 1.0976 0.3859 0.5546 0.101 Uiso 1 1 calc R U . . .
C36 C 0.8977(4) 0.3175(4) 0.4816(2) 0.0765(9) Uani 1 1 d . . . . .
H36 H 0.8415 0.3365 0.5270 0.092 Uiso 1 1 calc R U . . .
C37 C 0.8266(3) 0.2586(3) 0.39677(17) 0.0515(5) Uani 1 1 d . . . . .
C41 C 0.6748(2) 0.5507(2) 0.21727(12) 0.0349(4) Uani 1 1 d . . . . .
C42 C 0.6220(2) 0.63455(19) 0.28365(12) 0.0331(4) Uani 1 1 d . . . . .
C43 C 0.5626(2) 0.5902(2) 0.36247(13) 0.0393(4) Uani 1 1 d . . . . .
C44 C 0.5081(3) 0.6698(3) 0.42030(15) 0.0530(6) Uani 1 1 d . . . . .
H44 H 0.4654 0.6388 0.4719 0.064 Uiso 1 1 calc R U . . .
C45 C 0.5169(3) 0.7927(3) 0.40167(17) 0.0573(6) Uani 1 1 d . . . . .
H45 H 0.4804 0.8449 0.4408 0.069 Uiso 1 1 calc R U . . .
C46 C 0.5796(3) 0.8404(3) 0.32517(19) 0.0573(6) Uani 1 1 d . . . . .
H46 H 0.5883 0.9256 0.3139 0.069 Uiso 1 1 calc R U . . .
C47 C 0.6295(3) 0.7606(2) 0.26546(16) 0.0455(5) Uani 1 1 d . . . . .
H47 H 0.6682 0.7910 0.2130 0.055 Uiso 1 1 calc R U . . .
Cu1 Cu 0.72034(2) 0.33195(2) 0.14107(2) 0.03139(9) Uani 1 1 d . . . . .
N1 N 0.49785(17) 0.23275(16) 0.08886(11) 0.0327(3) Uani 1 1 d . . . . .
N2 N 0.75344(16) 0.26026(15) 0.02367(10) 0.0288(3) Uani 1 1 d . . . . .
N3 N 0.95549(18) 0.42119(16) 0.14481(10) 0.0325(3) Uani 1 1 d . . . . .
O1 O 0.70450(16) 0.16445(16) 0.21877(10) 0.0422(3) Uani 1 1 d . . . . .
O2 O 0.9122(2) 0.1297(2) 0.18036(12) 0.0576(4) Uani 1 1 d . . . . .
O3 O 0.68203(18) 0.44281(15) 0.24110(9) 0.0398(3) Uani 1 1 d . . . . .
O4 O 0.7080(2) 0.58354(18) 0.14313(10) 0.0531(4) Uani 1 1 d . . . . .
O5 O 0.5531(3) 0.4727(2) 0.38593(13) 0.0681(5) Uani 1 1 d D . . . .
O6 O 0.6779(2) 0.2342(3) 0.38216(15) 0.0737(6) Uani 1 1 d D . . . .
H5O H 0.584(5) 0.422(4) 0.343(2) 0.111 Uiso 1 1 d D U . . .
H6O H 0.664(5) 0.206(4) 0.3226(13) 0.111 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
C1 N3 1.336(2) . ?
C1 C2 1.387(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.367(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.397(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.381(2) . ?
C4 H4 0.9300 . ?
C5 N3 1.359(2) . ?
C5 C6 1.485(2) . ?
C6 N2 1.336(2) . ?
C6 C7 1.391(2) . ?
C7 C8 1.402(2) . ?
C7 H7 0.9300 . ?
C8 C9 1.404(2) . ?
C8 C16 1.481(2) . ?
C9 C10 1.382(2) . ?
C9 H9 0.9300 . ?
C10 N2 1.339(2) . ?
C10 C11 1.478(2) . ?
C11 N1 1.352(2) . ?
C11 C12 1.381(3) . ?
C12 C13 1.390(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.375(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.385(3) . ?
C14 H14 0.9300 . ?
C15 N1 1.335(2) . ?
C15 H15 0.9300 . ?
C16 C21 1.379(3) . ?
C16 C17 1.391(3) . ?
C17 C18 1.389(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.373(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.358(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.380(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C31 O2 1.233(3) . ?
C31 O1 1.296(2) . ?
C31 C32 1.494(3) . ?
C32 C33 1.401(3) . ?
C32 C37 1.403(3) . ?
C33 C34 1.389(4) . ?
C33 H33 0.9300 . ?
C34 C35 1.376(5) . ?
C34 H34 0.9300 . ?
C35 C36 1.373(5) . ?
C35 H35 0.9300 . ?
C36 C37 1.394(4) . ?
C36 H36 0.9300 . ?
C37 O6 1.340(3) . ?
C41 O4 1.237(2) . ?
C41 O3 1.293(2) . ?
C41 C42 1.492(2) . ?
C41 Cu1 2.6846(19) . ?
C42 C43 1.396(3) . ?
C42 C47 1.399(3) . ?
C43 O5 1.333(3) . ?
C43 C44 1.396(3) . ?
C44 C45 1.364(4) . ?
C44 H44 0.9300 . ?
C45 C46 1.384(4) . ?
C45 H45 0.9300 . ?
C46 C47 1.387(3) . ?
C46 H46 0.9300 . ?
C47 H47 0.9300 . ?
Cu1 N2 1.9331(15) . ?
Cu1 O3 1.9393(13) . ?
Cu1 N1 2.0412(16) . ?
Cu1 N3 2.0460(16) . ?
Cu1 O1 2.2505(15) . ?
O5 H5O 0.923(19) . ?
O6 H6O 0.908(19) . ?

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
N3 C1 C2 122.02(19) . . ?
N3 C1 H1 119.0 . . ?
C2 C1 H1 119.0 . . ?
C3 C2 C1 119.19(18) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C2 C3 C4 119.64(19) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 118.28(18) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
N3 C5 C4 121.94(16) . . ?
N3 C5 C6 113.91(15) . . ?
C4 C5 C6 124.15(16) . . ?
N2 C6 C7 120.55(15) . . ?
N2 C6 C5 112.46(15) . . ?
C7 C6 C5 126.98(15) . . ?
C6 C7 C8 119.63(16) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C7 C8 C9 117.94(16) . . ?
C7 C8 C16 122.14(16) . . ?
C9 C8 C16 119.88(16) . . ?
C10 C9 C8 119.46(16) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
N2 C10 C9 121.02(16) . . ?
N2 C10 C11 112.96(15) . . ?
C9 C10 C11 125.98(16) . . ?
N1 C11 C12 122.21(17) . . ?
N1 C11 C10 114.39(15) . . ?
C12 C11 C10 123.40(17) . . ?
C11 C12 C13 118.29(19) . . ?
C11 C12 H12 120.9 . . ?
C13 C12 H12 120.9 . . ?
C14 C13 C12 119.67(19) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
C13 C14 C15 118.79(19) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
N1 C15 C14 122.3(2) . . ?
N1 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
C21 C16 C17 117.62(19) . . ?
C21 C16 C8 121.67(18) . . ?
C17 C16 C8 120.71(18) . . ?
C18 C17 C16 120.7(2) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C19 C18 C17 120.2(2) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C20 C19 C18 119.4(2) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C19 C20 C21 120.8(3) . . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
C16 C21 C20 121.2(2) . . ?
C16 C21 H21 119.4 . . ?
C20 C21 H21 119.4 . . ?
O2 C31 O1 123.2(2) . . ?
O2 C31 C32 120.13(19) . . ?
O1 C31 C32 116.62(19) . . ?
C33 C32 C37 118.5(2) . . ?
C33 C32 C31 119.5(2) . . ?
C37 C32 C31 121.9(2) . . ?
C34 C33 C32 120.8(3) . . ?
C34 C33 H33 119.6 . . ?
C32 C33 H33 119.6 . . ?
C35 C34 C33 119.3(3) . . ?
C35 C34 H34 120.4 . . ?
C33 C34 H34 120.4 . . ?
C36 C35 C34 121.5(3) . . ?
C36 C35 H35 119.3 . . ?
C34 C35 H35 119.3 . . ?
C35 C36 C37 119.7(3) . . ?
C35 C36 H36 120.2 . . ?
C37 C36 H36 120.2 . . ?
O6 C37 C36 118.4(3) . . ?
O6 C37 C32 121.4(2) . . ?
C36 C37 C32 120.2(3) . . ?
O4 C41 O3 122.52(18) . . ?
O4 C41 C42 120.83(19) . . ?
O3 C41 C42 116.64(16) . . ?
O4 C41 Cu1 80.38(12) . . ?
O3 C41 Cu1 42.51(8) . . ?
C42 C41 Cu1 157.95(14) . . ?
C43 C42 C47 118.95(18) . . ?
C43 C42 C41 122.15(18) . . ?
C47 C42 C41 118.89(18) . . ?
O5 C43 C42 123.12(18) . . ?
O5 C43 C44 117.1(2) . . ?
C42 C43 C44 119.8(2) . . ?
C45 C44 C43 120.4(2) . . ?
C45 C44 H44 119.8 . . ?
C43 C44 H44 119.8 . . ?
C44 C45 C46 120.7(2) . . ?
C44 C45 H45 119.7 . . ?
C46 C45 H45 119.7 . . ?
C45 C46 C47 119.6(2) . . ?
C45 C46 H46 120.2 . . ?
C47 C46 H46 120.2 . . ?
C46 C47 C42 120.4(2) . . ?
C46 C47 H47 119.8 . . ?
C42 C47 H47 119.8 . . ?
N2 Cu1 O3 163.78(6) . . ?
N2 Cu1 N1 80.11(6) . . ?
O3 Cu1 N1 96.92(6) . . ?
N2 Cu1 N3 79.52(6) . . ?
O3 Cu1 N3 101.04(6) . . ?
N1 Cu1 N3 158.83(7) . . ?
N2 Cu1 O1 102.06(6) . . ?
O3 Cu1 O1 94.02(6) . . ?
N1 Cu1 O1 93.53(6) . . ?
N3 Cu1 O1 96.27(6) . . ?
N2 Cu1 C41 137.03(6) . . ?
O3 Cu1 C41 26.78(6) . . ?
N1 Cu1 C41 92.78(6) . . ?
N3 Cu1 C41 98.20(6) . . ?
O1 Cu1 C41 120.74(6) . . ?
C15 N1 C11 118.75(16) . . ?
C15 N1 Cu1 127.53(14) . . ?
C11 N1 Cu1 113.69(12) . . ?
C6 N2 C10 121.36(15) . . ?
C6 N2 Cu1 119.88(12) . . ?
C10 N2 Cu1 118.74(12) . . ?
C1 N3 C5 118.88(16) . . ?
C1 N3 Cu1 126.84(14) . . ?
C5 N3 Cu1 114.20(11) . . ?
C31 O1 Cu1 110.49(13) . . ?
C41 O3 Cu1 110.71(12) . . ?
C43 O5 H5O 113(3) . . ?
C37 O6 H6O 101(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C4 H4 O4 0.93 2.44 3.338(3) 161.3 2_765
C7 H7 O4 0.93 2.58 3.454(3) 156.6 2_765
C12 H12 O1 0.93 2.60 3.477(3) 157.3 2_655
C12 H12 O2 0.93 2.52 3.147(3) 125.2 2_655
C14 H14 O2 0.93 2.32 3.252(3) 176.4 1_455

_refine_diff_density_max         1.484
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.063

_shelxl_version_number           2014-3

