# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 1984638'
loop_
_audit_author_name
_audit_author_address
'Takashiro Akitsu'
;Tokyo University of Science
Japan
;
_audit_update_record             
;
2020-02-18 deposited with the CCDC.	2020-09-02 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C10 H11 Cu N O5'
_chemical_formula_sum            'C10 H11 Cu N O5'
_chemical_formula_iupac          ?
_chemical_formula_weight         288.74
_chemical_absolute_configuration Syn

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   5.8152(7)
_cell_length_b                   19.930(3)
_cell_length_c                   9.4998(12)
_cell_angle_alpha                90
_cell_angle_beta                 102.749(2)
_cell_angle_gamma                90
_cell_volume                     1073.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4233
_cell_measurement_theta_min      2.1980
_cell_measurement_theta_max      27.5036
_cell_measurement_temperature    173

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.32
_exptl_crystal_density_diffrn    1.786
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             588

_exptl_absorpt_coefficient_mu    2.043
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.6357
_exptl_absorpt_correction_T_max  0.7456

_exptl_special_details           
;
;

_diffrn_ambient_temperature      173

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            5919
_diffrn_reflns_av_R_equivalents  0.0149
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_theta_min         2.04
_diffrn_reflns_theta_max         27.55
_diffrn_reflns_theta_full        27.55
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       10

_refine_special_details          
;
;

_reflns_number_total             4192
_reflns_number_gt                3998
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0226
_refine_ls_R_factor_gt           0.0211
_refine_ls_wR_factor_gt          0.0473
_refine_ls_wR_factor_ref         0.0478
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_number_reflns         4192
_refine_ls_number_parameters     324
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w=1/[σ²(Fo²)] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.327
_refine_diff_density_min         -0.233
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack x determined using 1545 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.017(6)

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

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu1 0.55404(7) 0.52149(2) 0.58847(4) 0.01673(10) Uani d . . . 1 . .
Cu Cu2 0.88274(7) 0.47053(2) 0.86185(4) 0.01642(10) Uani d . . . 1 . .
O O5 0.8607(4) 0.54135(10) 0.7123(2) 0.0173(5) Uani d . . . 1 . .
O O1 0.5788(4) 0.44962(10) 0.7378(2) 0.0177(5) Uani d . . . 1 . .
O O3 1.4636(4) 0.44505(13) 1.1613(3) 0.0264(6) Uani d . . . 1 . .
O O8 0.2416(4) 0.50775(12) 0.4697(2) 0.0236(6) Uani d . . . 1 . .
O O6 1.5786(4) 0.66091(12) 0.8783(3) 0.0253(6) Uani d . . . 1 . .
H H2H 1.6163 0.6237 0.9184 0.038 Uiso calc U . R 1 . .
O O11W 0.7213(5) 0.44995(14) 0.4341(3) 0.0233(6) Uani d . . . 1 . .
H H4W 0.6234 0.4445 0.3556 0.035 Uiso calc U . R 1 . .
O O4 1.2027(4) 0.48065(12) 0.9704(2) 0.0215(6) Uani d . . . 1 . .
N N2 0.5351(5) 0.60534(13) 0.4849(3) 0.0167(6) Uani d . . . 1 . .
O O2 -0.1499(4) 0.33371(12) 0.5869(3) 0.0275(6) Uani d . . . 1 . .
H H1H -0.1826 0.3695 0.5402 0.041 Uiso calc U . R 1 . .
O O7 -0.0399(4) 0.55200(13) 0.3013(3) 0.0270(6) Uani d . . . 1 . .
N N1 0.8773(5) 0.39673(14) 0.9921(3) 0.0189(6) Uani d . . . 1 . .
C C12 1.2205(6) 0.60014(16) 0.7927(4) 0.0196(8) Uani d . . . 1 . .
H H12 1.2803 0.5633 0.8534 0.024 Uiso calc U . R 1 . .
C C16 0.9088(6) 0.65104(17) 0.6129(4) 0.0163(7) Uani d . . . 1 . .
C C11 0.9942(6) 0.59616(16) 0.7059(3) 0.0159(7) Uani d . . . 1 . .
C C19 0.1603(7) 0.55454(18) 0.3813(4) 0.0209(8) Uani d . . . 1 . .
C C7 0.7223(6) 0.34965(17) 0.9735(4) 0.0204(8) Uani d . . . 1 . .
H H7 0.7477 0.3137 1.0409 0.025 Uiso calc U . R 1 . .
C C14 1.2770(7) 0.71136(17) 0.7035(4) 0.0220(8) Uani d . . . 1 . .
H H14 1.3705 0.7505 0.7041 0.026 Uiso calc U . R 1 . .
C C3 0.0703(7) 0.33811(18) 0.6720(4) 0.0211(8) Uani d . . . 1 . .
C C1 0.4408(6) 0.39707(16) 0.7524(4) 0.0168(7) Uani d . . . 1 . .
C C6 0.5147(6) 0.34674(16) 0.8601(4) 0.0184(7) Uani d . . . 1 . .
C C17 0.6867(6) 0.65305(16) 0.5116(4) 0.0181(7) Uani d . . . 1 . .
H H17 0.6478 0.6936 0.459 0.022 Uiso calc U . R 1 . .
C C15 1.0589(7) 0.70715(17) 0.6162(4) 0.0203(8) Uani d . . . 1 . .
H H15 1.004 0.7438 0.5539 0.024 Uiso calc U . R 1 . .
C C13 1.3616(6) 0.65658(17) 0.7931(4) 0.0187(7) Uani d . . . 1 . .
C C2 0.2185(6) 0.39151(17) 0.6620(4) 0.0205(8) Uani d . . . 1 . .
H H2 0.1668 0.4252 0.5914 0.025 Uiso calc U . R 1 . .
C C18 0.3148(6) 0.61531(16) 0.3754(3) 0.0181(7) Uani d . . . 1 . .
H H18 0.233 0.6561 0.4014 0.022 Uiso calc U . R 1 . .
C C9 1.2621(6) 0.44416(17) 1.0832(4) 0.0201(8) Uani d . . . 1 . .
C C5 0.3593(6) 0.29166(18) 0.8624(4) 0.0231(9) Uani d . . . 1 . .
H H5 0.4092 0.2568 0.9306 0.028 Uiso calc U . R 1 . .
C C8 1.0690(6) 0.40078(18) 1.1228(4) 0.0220(8) Uani d . . . 1 . .
H H8 1.0046 0.4272 1.195 0.026 Uiso calc U . R 1 . .
C C20 0.3585(7) 0.6245(2) 0.2244(4) 0.0291(9) Uani d . . . 1 . .
H H20C 0.4585 0.664 0.2229 0.044 Uiso calc U . R 1 . .
H H20B 0.2076 0.6309 0.1555 0.044 Uiso calc U . R 1 . .
H H20A 0.4376 0.5846 0.1975 0.044 Uiso calc U . R 1 . .
C C4 0.1431(7) 0.28637(17) 0.7719(4) 0.0259(8) Uani d . . . 1 . .
H H4 0.0445 0.2488 0.7763 0.031 Uiso calc U . R 1 . .
C C10 1.1575(7) 0.3359(2) 1.1957(5) 0.0416(11) Uani d . . . 1 . .
H H10B 1.0368 0.3168 1.2413 0.062 Uiso calc U . R 1 . .
H H10C 1.3015 0.3443 1.2694 0.062 Uiso calc U . R 1 . .
H H10A 1.1918 0.3044 1.1239 0.062 Uiso calc U . R 1 . .
H H3W 0.796(8) 0.472(3) 0.416(5) 0.047(17) Uiso d . . . 1 . .
O O10W 0.7196(5) 0.54357(14) 1.0216(3) 0.0234(6) Uani d . . . 1 . .
H H1W 0.646(6) 0.523(2) 1.037(4) 0.013(12) Uiso d . . . 1 . .
H H2W 0.820(11) 0.550(3) 1.115(7) 0.12(3) Uiso d . . . 1 . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 N2 . 1.930(3) ?
Cu1 O8 . 1.935(2) ?
Cu1 O5 . 1.948(2) ?
Cu1 O1 . 1.999(2) ?
Cu1 O11W . 2.400(3) ?
Cu1 Cu2 . 3.0396(5) ?
Cu2 N1 . 1.927(3) ?
Cu2 O4 . 1.929(2) ?
Cu2 O1 . 1.941(2) ?
Cu2 O5 . 1.987(2) ?
Cu2 O10W . 2.441(3) ?
O5 C11 . 1.349(4) ?
O1 C1 . 1.346(4) ?
O3 C9 . 1.241(4) ?
O8 C19 . 1.274(4) ?
O6 C13 . 1.343(4) ?
O6 H2H . 0.84 ?
O11W H4W . 0.84 ?
O11W H3W . 0.67(5) ?
O4 C9 . 1.278(4) ?
N2 C17 . 1.283(4) ?
N2 C18 . 1.474(4) ?
O2 C3 . 1.358(4) ?
O2 H1H . 0.84 ?
O7 C19 . 1.243(4) ?
N1 C7 . 1.286(4) ?
N1 C8 . 1.477(4) ?
C12 C13 . 1.392(5) ?
C12 C11 . 1.392(5) ?
C12 H12 . 0.95 ?
C16 C15 . 1.415(5) ?
C16 C11 . 1.425(5) ?
C16 C17 . 1.431(5) ?
C19 C18 . 1.517(5) ?
C7 C6 . 1.431(5) ?
C7 H7 . 0.95 ?
C14 C15 . 1.356(5) ?
C14 C13 . 1.405(5) ?
C14 H14 . 0.95 ?
C3 C2 . 1.386(5) ?
C3 C4 . 1.402(5) ?
C1 C2 . 1.389(5) ?
C1 C6 . 1.429(5) ?
C6 C5 . 1.425(5) ?
C17 H17 . 0.95 ?
C15 H15 . 0.95 ?
C2 H2 . 0.95 ?
C18 C20 . 1.522(5) ?
C18 H18 . 1.0 ?
C9 C8 . 1.528(5) ?
C5 C4 . 1.362(5) ?
C5 H5 . 0.95 ?
C8 C10 . 1.503(5) ?
C8 H8 . 1.0 ?
C20 H20C . 0.98 ?
C20 H20B . 0.98 ?
C20 H20A . 0.98 ?
C4 H4 . 0.95 ?
C10 H10B . 0.98 ?
C10 H10C . 0.98 ?
C10 H10A . 0.98 ?
O10W H1W . 0.63(4) ?
O10W H2W . 0.95(6) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N2 Cu1 O8 . . 83.37(11) ?
N2 Cu1 O5 . . 94.22(10) ?
O8 Cu1 O5 . . 175.96(10) ?
N2 Cu1 O1 . . 165.80(10) ?
O8 Cu1 O1 . . 102.93(10) ?
O5 Cu1 O1 . . 78.70(9) ?
N2 Cu1 O11W . . 100.85(11) ?
O8 Cu1 O11W . . 90.83(10) ?
O5 Cu1 O11W . . 92.82(10) ?
O1 Cu1 O11W . . 91.85(9) ?
N2 Cu1 Cu2 . . 132.79(8) ?
O8 Cu1 Cu2 . . 141.58(7) ?
O5 Cu1 Cu2 . . 39.89(6) ?
O1 Cu1 Cu2 . . 38.82(7) ?
O11W Cu1 Cu2 . . 93.46(6) ?
N1 Cu2 O4 . . 83.51(11) ?
N1 Cu2 O1 . . 94.83(10) ?
O4 Cu2 O1 . . 171.49(10) ?
N1 Cu2 O5 . . 173.70(11) ?
O4 Cu2 O5 . . 102.16(10) ?
O1 Cu2 O5 . . 79.15(9) ?
N1 Cu2 O10W . . 89.56(11) ?
O4 Cu2 O10W . . 93.81(10) ?
O1 Cu2 O10W . . 94.52(10) ?
O5 Cu2 O10W . . 92.77(9) ?
N1 Cu2 Cu1 . . 135.02(9) ?
O4 Cu2 Cu1 . . 140.59(7) ?
O1 Cu2 Cu1 . . 40.20(6) ?
O5 Cu2 Cu1 . . 38.96(7) ?
O10W Cu2 Cu1 . . 94.27(7) ?
C11 O5 Cu1 . . 126.6(2) ?
C11 O5 Cu2 . . 131.3(2) ?
Cu1 O5 Cu2 . . 101.15(10) ?
C1 O1 Cu2 . . 126.0(2) ?
C1 O1 Cu1 . . 132.9(2) ?
Cu2 O1 Cu1 . . 100.98(10) ?
C19 O8 Cu1 . . 116.4(2) ?
C13 O6 H2H . . 109.5 ?
Cu1 O11W H4W . . 109.5 ?
Cu1 O11W H3W . . 98.(4) ?
H4W O11W H3W . . 101.9 ?
C9 O4 Cu2 . . 116.1(2) ?
C17 N2 C18 . . 119.4(3) ?
C17 N2 Cu1 . . 125.5(2) ?
C18 N2 Cu1 . . 114.8(2) ?
C3 O2 H1H . . 109.5 ?
C7 N1 C8 . . 122.1(3) ?
C7 N1 Cu2 . . 125.4(2) ?
C8 N1 Cu2 . . 112.4(2) ?
C13 C12 C11 . . 121.8(3) ?
C13 C12 H12 . . 119.1 ?
C11 C12 H12 . . 119.1 ?
C15 C16 C11 . . 117.7(3) ?
C15 C16 C17 . . 117.0(3) ?
C11 C16 C17 . . 125.3(3) ?
O5 C11 C12 . . 119.8(3) ?
O5 C11 C16 . . 121.6(3) ?
C12 C11 C16 . . 118.6(3) ?
O7 C19 O8 . . 122.3(3) ?
O7 C19 C18 . . 119.5(3) ?
O8 C19 C18 . . 118.2(3) ?
N1 C7 C6 . . 125.6(3) ?
N1 C7 H7 . . 117.2 ?
C6 C7 H7 . . 117.2 ?
C15 C14 C13 . . 118.5(3) ?
C15 C14 H14 . . 120.7 ?
C13 C14 H14 . . 120.7 ?
O2 C3 C2 . . 121.8(3) ?
O2 C3 C4 . . 117.4(3) ?
C2 C3 C4 . . 120.8(3) ?
O1 C1 C2 . . 119.5(3) ?
O1 C1 C6 . . 121.9(3) ?
C2 C1 C6 . . 118.6(3) ?
C5 C6 C1 . . 117.4(3) ?
C5 C6 C7 . . 116.9(3) ?
C1 C6 C7 . . 125.5(3) ?
N2 C17 C16 . . 126.2(3) ?
N2 C17 H17 . . 116.9 ?
C16 C17 H17 . . 116.9 ?
C14 C15 C16 . . 123.5(3) ?
C14 C15 H15 . . 118.3 ?
C16 C15 H15 . . 118.3 ?
O6 C13 C12 . . 121.9(3) ?
O6 C13 C14 . . 118.2(3) ?
C12 C13 C14 . . 119.9(3) ?
C3 C2 C1 . . 121.8(3) ?
C3 C2 H2 . . 119.1 ?
C1 C2 H2 . . 119.1 ?
N2 C18 C19 . . 107.2(3) ?
N2 C18 C20 . . 112.4(3) ?
C19 C18 C20 . . 110.8(3) ?
N2 C18 H18 . . 108.8 ?
C19 C18 H18 . . 108.8 ?
C20 C18 H18 . . 108.8 ?
O3 C9 O4 . . 122.5(3) ?
O3 C9 C8 . . 120.6(3) ?
O4 C9 C8 . . 116.8(3) ?
C4 C5 C6 . . 123.4(3) ?
C4 C5 H5 . . 118.3 ?
C6 C5 H5 . . 118.3 ?
N1 C8 C10 . . 117.3(3) ?
N1 C8 C9 . . 106.5(3) ?
C10 C8 C9 . . 113.9(3) ?
N1 C8 H8 . . 106.1 ?
C10 C8 H8 . . 106.1 ?
C9 C8 H8 . . 106.1 ?
C18 C20 H20C . . 109.5 ?
C18 C20 H20B . . 109.5 ?
H20C C20 H20B . . 109.5 ?
C18 C20 H20A . . 109.5 ?
H20C C20 H20A . . 109.5 ?
H20B C20 H20A . . 109.5 ?
C5 C4 C3 . . 118.0(3) ?
C5 C4 H4 . . 121.0 ?
C3 C4 H4 . . 121.0 ?
C8 C10 H10B . . 109.5 ?
C8 C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
C8 C10 H10A . . 109.5 ?
H10B C10 H10A . . 109.5 ?
H10C C10 H10A . . 109.5 ?
Cu2 O10W H1W . . 98.(4) ?
Cu2 O10W H2W . . 114.(4) ?
H1W O10W H2W . . 100.(5) ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Cu1 O5 C11 C12 . . . . -173.7(2) ?
Cu2 O5 C11 C12 . . . . 19.3(5) ?
Cu1 O5 C11 C16 . . . . 6.9(4) ?
Cu2 O5 C11 C16 . . . . -160.1(2) ?
C13 C12 C11 O5 . . . . -177.9(3) ?
C13 C12 C11 C16 . . . . 1.5(5) ?
C15 C16 C11 O5 . . . . 178.4(3) ?
C17 C16 C11 O5 . . . . -4.4(5) ?
C15 C16 C11 C12 . . . . -1.0(5) ?
C17 C16 C11 C12 . . . . 176.2(3) ?
Cu1 O8 C19 O7 . . . . -178.7(3) ?
Cu1 O8 C19 C18 . . . . 1.1(4) ?
C8 N1 C7 C6 . . . . 171.4(3) ?
Cu2 N1 C7 C6 . . . . -6.0(5) ?
Cu2 O1 C1 C2 . . . . 174.8(2) ?
Cu1 O1 C1 C2 . . . . -9.8(4) ?
Cu2 O1 C1 C6 . . . . -4.4(4) ?
Cu1 O1 C1 C6 . . . . 171.0(2) ?
O1 C1 C6 C5 . . . . -177.3(3) ?
C2 C1 C6 C5 . . . . 3.4(5) ?
O1 C1 C6 C7 . . . . 8.3(5) ?
C2 C1 C6 C7 . . . . -171.0(3) ?
N1 C7 C6 C5 . . . . -177.2(3) ?
N1 C7 C6 C1 . . . . -2.8(6) ?
C18 N2 C17 C16 . . . . -179.3(3) ?
Cu1 N2 C17 C16 . . . . 6.5(5) ?
C15 C16 C17 N2 . . . . 174.4(3) ?
C11 C16 C17 N2 . . . . -2.8(6) ?
C13 C14 C15 C16 . . . . 1.6(6) ?
C11 C16 C15 C14 . . . . -0.6(5) ?
C17 C16 C15 C14 . . . . -178.0(3) ?
C11 C12 C13 O6 . . . . 179.0(3) ?
C11 C12 C13 C14 . . . . -0.4(5) ?
C15 C14 C13 O6 . . . . 179.4(3) ?
C15 C14 C13 C12 . . . . -1.1(5) ?
O2 C3 C2 C1 . . . . 177.8(3) ?
C4 C3 C2 C1 . . . . -1.9(5) ?
O1 C1 C2 C3 . . . . 179.5(3) ?
C6 C1 C2 C3 . . . . -1.2(5) ?
C17 N2 C18 C19 . . . . -173.1(3) ?
Cu1 N2 C18 C19 . . . . 1.8(3) ?
C17 N2 C18 C20 . . . . 64.9(4) ?
Cu1 N2 C18 C20 . . . . -120.2(3) ?
O7 C19 C18 N2 . . . . 177.9(3) ?
O8 C19 C18 N2 . . . . -1.8(4) ?
O7 C19 C18 C20 . . . . -59.1(4) ?
O8 C19 C18 C20 . . . . 121.2(3) ?
Cu2 O4 C9 O3 . . . . 178.8(3) ?
Cu2 O4 C9 C8 . . . . -3.8(4) ?
C1 C6 C5 C4 . . . . -2.7(5) ?
C7 C6 C5 C4 . . . . 172.1(3) ?
C7 N1 C8 C10 . . . . 30.3(5) ?
Cu2 N1 C8 C10 . . . . -152.0(3) ?
C7 N1 C8 C9 . . . . 159.2(3) ?
Cu2 N1 C8 C9 . . . . -23.1(3) ?
O3 C9 C8 N1 . . . . -165.0(3) ?
O4 C9 C8 N1 . . . . 17.6(4) ?
O3 C9 C8 C10 . . . . -34.2(5) ?
O4 C9 C8 C10 . . . . 148.4(3) ?
C6 C5 C4 C3 . . . . -0.3(5) ?
O2 C3 C4 C5 . . . . -177.1(3) ?
C2 C3 C4 C5 . . . . 2.6(5) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O10W H2W O7 1_656 0.95(6) 1.78(6) 2.721(4) 168.(6) ?
O10W H1W O4 1_455 0.63(4) 2.66(4) 3.194(4) 145.(4) ?
O10W H1W O3 1_455 0.63(4) 2.35(4) 2.950(4) 162.(4) ?
O11W H3W O7 1_655 0.67(5) 2.26(5) 2.903(4) 164.(5) ?
O11W H3W O8 1_655 0.67(5) 2.63(5) 3.185(4) 143.(5) ?
C2 H2 O8 . 0.95 2.11 2.972(4) 150.0 ?
C12 H12 O4 . 0.95 2.09 2.934(4) 146.9 ?
O2 H1H O11W 1_455 0.84 1.91 2.748(4) 176.1 ?
O11W H4W O3 1_454 0.84 1.87 2.694(4) 164.9 ?
O6 H2H O10W 1_655 0.84 1.9 2.739(4) 175.2 ?
O10W H2W O7 1_656 0.95(6) 1.78(6) 2.721(4) 168.(6) ?
O10W H1W O4 1_455 0.63(4) 2.66(4) 3.194(4) 145.(4) ?
O10W H1W O3 1_455 0.63(4) 2.35(4) 2.950(4) 162.(4) ?
O11W H3W O7 1_655 0.67(5) 2.26(5) 2.903(4) 164.(5) ?
O11W H3W O8 1_655 0.67(5) 2.63(5) 3.185(4) 143.(5) ?
C2 H2 O8 . 0.95 2.11 2.972(4) 150.0 ?
C12 H12 O4 . 0.95 2.09 2.934(4) 146.9 ?
O2 H1H O11W 1_455 0.84 1.91 2.748(4) 176.1 ?
O11W H4W O3 1_454 0.84 1.87 2.694(4) 164.9 ?
O6 H2H O10W 1_655 0.84 1.9 2.739(4) 175.2 ?
O10W H2W O7 1_656 0.95(6) 1.78(6) 2.721(4) 168.(6) ?
O10W H1W O4 1_455 0.63(4) 2.66(4) 3.194(4) 145.(4) ?
O10W H1W O3 1_455 0.63(4) 2.35(4) 2.950(4) 162.(4) ?
O11W H3W O7 1_655 0.67(5) 2.26(5) 2.903(4) 164.(5) ?
O11W H3W O8 1_655 0.67(5) 2.63(5) 3.185(4) 143.(5) ?
C2 H2 O8 . 0.95 2.11 2.972(4) 150.0 ?
C12 H12 O4 . 0.95 2.09 2.934(4) 146.9 ?
O2 H1H O11W 1_455 0.84 1.91 2.748(4) 176.1 ?
O11W H4W O3 1_454 0.84 1.87 2.694(4) 164.9 ?
O6 H2H O10W 1_655 0.84 1.9 2.739(4) 175.2 ?
O6 H2H O10W 1_655 0.84 1.9 2.739(4) 175.2 ?
O11W H4W O3 1_454 0.84 1.87 2.694(4) 164.9 ?
O2 H1H O11W 1_455 0.84 1.91 2.748(4) 176.1 ?
C12 H12 O4 . 0.95 2.09 2.934(4) 146.9 ?
C2 H2 O8 . 0.95 2.11 2.972(4) 150.0 ?
O11W H3W O8 1_655 0.67(5) 2.63(5) 3.185(4) 143.(5) ?
O11W H3W O7 1_655 0.67(5) 2.26(5) 2.903(4) 164.(5) ?
O10W H1W O3 1_455 0.63(4) 2.35(4) 2.950(4) 162.(4) ?
O10W H1W O4 1_455 0.63(4) 2.66(4) 3.194(4) 145.(4) ?
O10W H2W O7 1_656 0.95(6) 1.78(6) 2.721(4) 168.(6) ?
O6 H2H O10W 1_655 0.84 1.9 2.739(4) 175.2 ?
O11W H4W O3 1_454 0.84 1.87 2.694(4) 164.9 ?
O2 H1H O11W 1_455 0.84 1.91 2.748(4) 176.1 ?
C12 H12 O4 . 0.95 2.09 2.934(4) 146.9 ?
C2 H2 O8 . 0.95 2.11 2.972(4) 150.0 ?
O11W H3W O8 1_655 0.67(5) 2.63(5) 3.185(4) 143.(5) ?
O11W H3W O7 1_655 0.67(5) 2.26(5) 2.903(4) 164.(5) ?
O10W H1W O3 1_455 0.63(4) 2.35(4) 2.950(4) 162.(4) ?
O10W H1W O4 1_455 0.63(4) 2.66(4) 3.194(4) 145.(4) ?
O10W H2W O7 1_656 0.95(6) 1.78(6) 2.721(4) 168.(6) ?

####################################################################### 
# 
# 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_CuGDB2
_database_code_depnum_ccdc_archive 'CCDC 1984655'
loop_
_audit_author_name
_audit_author_address
'Takashiro Akitsu'
;Tokyo University of Science
Japan
;
_audit_update_record             
;
2020-02-18 deposited with the CCDC.	2020-09-02 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C9 H8 Cu N O4'
_chemical_formula_sum            'C9 H8 Cu N O4'
_chemical_formula_iupac          ?
_chemical_formula_weight         257.70

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   6.3126(13)
_cell_length_b                   13.094(3)
_cell_length_c                   11.740(3)
_cell_angle_alpha                90
_cell_angle_beta                 91.632(8)
_cell_angle_gamma                90
_cell_volume                     970.0(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5665
_cell_measurement_theta_min      2.3365
_cell_measurement_theta_max      27.8578
_cell_measurement_temperature    173

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.765
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520

_exptl_absorpt_coefficient_mu    2.243
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
'SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction'
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_T_max  0.81

_exptl_special_details           
;
;

_diffrn_ambient_temperature      173

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker APEX-III CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 7.3910

_diffrn_reflns_number            11551
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_theta_min         2.33
_diffrn_reflns_theta_max         27.76
_diffrn_reflns_theta_full        27.76
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14

_refine_special_details          
;
;

_reflns_number_total             2260
_reflns_number_gt                1897
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_gt          0.1029
_refine_ls_wR_factor_ref         0.1294
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_restrained_S_all      0.968
_refine_ls_number_reflns         2260
_refine_ls_number_parameters     152
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.6062P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.702
_refine_diff_density_min         -0.572
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.011(2)

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

_computing_data_collection       
"Bruker APEX3'_computing_cell_refinement              'SAINT V8.38A (Bruker AXS Inc., 2017)"
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP-3 and Mercury'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu1 0.60608(5) 0.54002(2) 0.61011(3) 0.02250(19) Uani d . . . 1 . .
O O4 0.3708(3) 0.57183(16) 0.50943(17) 0.0231(4) Uani d . . . 1 . .
O O1 1.1109(3) 0.58524(16) 0.80872(18) 0.0297(5) Uani d . . . 1 . .
O O3 0.4059(4) 0.44356(19) 0.7191(2) 0.0293(5) Uani d . . . 1 . .
H H8 0.314221 0.478966 0.747568 0.044 Uiso calc U . R 1 . .
O O5 -0.2370(3) 0.74364(15) 0.37848(18) 0.0258(5) Uani d . . . 1 . .
H H6 -0.28036 0.80109 0.362632 0.039 Uiso calc U . R 1 . .
O O2 0.8539(3) 0.51263(17) 0.70611(19) 0.0308(5) Uani d . . . 1 . .
N N1 0.6496(3) 0.68094(17) 0.65685(18) 0.0179(4) Uani d . . . 1 . .
C C7 -0.0488(4) 0.7506(2) 0.4353(2) 0.0200(5) Uani d . . . 1 . .
C C3 0.5361(4) 0.7581(2) 0.6250(2) 0.0193(5) Uani d . . . 1 . .
H H3 0.581402 0.82257 0.648215 0.023 Uiso calc U . R 1 . .
C C4 0.3435(4) 0.7517(2) 0.5557(2) 0.0180(5) Uani d . . . 1 . .
C C2 0.8421(4) 0.6949(2) 0.7269(2) 0.0189(5) Uani d . . . 1 . .
H H1 0.807834 0.727083 0.798503 0.023 Uiso calc U . R 1 . .
H H2 0.940285 0.738723 0.687824 0.023 Uiso calc U . R 1 . .
C C5 0.2274(4) 0.8425(2) 0.5361(2) 0.0212(5) Uani d . . . 1 . .
H H4 0.282406 0.903597 0.564479 0.025 Uiso calc U . R 1 . .
C C9 0.2619(4) 0.6597(2) 0.5064(2) 0.0183(5) Uani d . . . 1 . .
C C1 0.9437(4) 0.5909(2) 0.7496(2) 0.0218(6) Uani d . . . 1 . .
C C8 0.0628(4) 0.6605(2) 0.4520(2) 0.0195(5) Uani d . . . 1 . .
H H7 0.003639 0.59929 0.426362 0.023 Uiso calc U . R 1 . .
C C6 0.0347(4) 0.8444(2) 0.4764(2) 0.0227(6) Uani d . . . 1 . .
H H5 -0.037459 0.905469 0.463695 0.027 Uiso calc U . R 1 . .
H H9 0.355(6) 0.392(3) 0.692(3) 0.036(10) Uiso d . . . 1 . .


_geom_special_details            
;

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 O4 . 1.9173(19) ?
Cu1 O2 . 1.935(2) ?
Cu1 N1 . 1.942(2) ?
Cu1 O4 3_666 2.037(2) ?
Cu1 O3 . 2.219(2) ?
O4 C9 . 1.340(3) ?
O1 C1 . 1.248(3) ?
O3 H8 . 0.82 ?
O3 H9 . 0.80(4) ?
O5 C7 . 1.349(3) ?
O5 H6 . 0.82 ?
O2 C1 . 1.271(3) ?
N1 C3 . 1.288(4) ?
N1 C2 . 1.459(3) ?
C7 C8 . 1.386(4) ?
C7 C6 . 1.416(4) ?
C3 C4 . 1.446(4) ?
C3 H3 . 0.93 ?
C4 C5 . 1.412(4) ?
C4 C9 . 1.427(4) ?
C2 C1 . 1.525(4) ?
C2 H1 . 0.97 ?
C2 H2 . 0.97 ?
C5 C6 . 1.387(4) ?
C5 H4 . 0.93 ?
C9 C8 . 1.394(3) ?
C8 H7 . 0.93 ?
C6 H5 . 0.93 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O4 Cu1 O2 . . 176.66(10) ?
O4 Cu1 N1 . . 93.94(9) ?
O2 Cu1 N1 . . 84.61(9) ?
O4 Cu1 O4 . 3_666 78.51(9) ?
O2 Cu1 O4 . 3_666 101.27(9) ?
N1 Cu1 O4 . 3_666 149.94(9) ?
O4 Cu1 O3 . . 92.01(9) ?
O2 Cu1 O3 . . 91.32(10) ?
N1 Cu1 O3 . . 117.15(9) ?
O4 Cu1 O3 3_666 . 92.35(9) ?
C9 O4 Cu1 . . 126.21(16) ?
C9 O4 Cu1 . 3_666 130.21(16) ?
Cu1 O4 Cu1 . 3_666 101.49(9) ?
Cu1 O3 H8 . . 109.5 ?
Cu1 O3 H9 . . 118.(3) ?
H8 O3 H9 . . 110.8 ?
C7 O5 H6 . . 109.5 ?
C1 O2 Cu1 . . 115.37(19) ?
C3 N1 C2 . . 120.9(2) ?
C3 N1 Cu1 . . 126.15(18) ?
C2 N1 Cu1 . . 112.76(16) ?
O5 C7 C8 . . 116.7(2) ?
O5 C7 C6 . . 122.8(2) ?
C8 C7 C6 . . 120.5(2) ?
N1 C3 C4 . . 124.8(2) ?
N1 C3 H3 . . 117.6 ?
C4 C3 H3 . . 117.6 ?
C5 C4 C9 . . 117.7(2) ?
C5 C4 C3 . . 117.9(2) ?
C9 C4 C3 . . 124.4(2) ?
N1 C2 C1 . . 109.0(2) ?
N1 C2 H1 . . 109.9 ?
C1 C2 H1 . . 109.9 ?
N1 C2 H2 . . 109.9 ?
C1 C2 H2 . . 109.9 ?
H1 C2 H2 . . 108.3 ?
C6 C5 C4 . . 122.8(2) ?
C6 C5 H4 . . 118.6 ?
C4 C5 H4 . . 118.6 ?
O4 C9 C8 . . 118.3(2) ?
O4 C9 C4 . . 122.3(2) ?
C8 C9 C4 . . 119.4(2) ?
O1 C1 O2 . . 122.4(3) ?
O1 C1 C2 . . 119.7(2) ?
O2 C1 C2 . . 118.0(2) ?
C7 C8 C9 . . 121.3(2) ?
C7 C8 H7 . . 119.4 ?
C9 C8 H7 . . 119.4 ?
C5 C6 C7 . . 118.0(2) ?
C5 C6 H5 . . 121.0 ?
C7 C6 H5 . . 121.0 ?

####################################################################### 
# 
# 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_I_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1984653'
loop_
_audit_author_name
_audit_author_address
'Takashiro Akitsu'
;Tokyo University of Science
Japan
;
_audit_update_record             
;
2020-02-18 deposited with the CCDC.	2020-09-02 downloaded from the CCDC.
;
_chemical_name_systematic        CuPDB
_chemical_name_common            ?
_chemical_formula_moiety         'C33 H32 Cu2 N2 O10, 2(C H4 O)'
_chemical_formula_sum            'C35 H40 Cu2 N2 O12'
_chemical_formula_iupac          ?
_chemical_formula_weight         807.79
_chemical_absolute_configuration Syn

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   7.3484(10)
_cell_length_b                   14.6316(19)
_cell_length_c                   16.822(2)
_cell_angle_alpha                90
_cell_angle_beta                 99.035(2)
_cell_angle_gamma                90
_cell_volume                     1786.2(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4742
_cell_measurement_theta_min      2.7842
_cell_measurement_theta_max      27.5017
_cell_measurement_temperature    173

_exptl_crystal_description       prism
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.056
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             836

_exptl_absorpt_coefficient_mu    1.256
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.71
_exptl_absorpt_correction_T_max  0.93

_exptl_special_details           
;
;

_diffrn_ambient_temperature      173

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            9909
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0481
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measured_fraction_theta_full 0.967
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20

_refine_special_details          
;
;

_reflns_number_total             5618
_reflns_number_gt                5136
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0343
_refine_ls_R_factor_gt           0.0296
_refine_ls_wR_factor_gt          0.0653
_refine_ls_wR_factor_ref         0.0671
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_restrained_S_all      0.976
_refine_ls_number_reflns         5618
_refine_ls_number_parameters     476
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0339P)²] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.437
_refine_diff_density_min         -0.442
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack x determined using 1207 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.023(9)

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 and Mercury'
_computing_publication_material  'Bruker SHELXTL'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu Cu1 0.36906(5) 0.52489(3) 0.68746(2) 0.01831(10) Uani d . . . 1 . .
Cu Cu2 0.06099(6) 0.46288(3) 0.77453(2) 0.01934(10) Uani d . . . 1 . .
O O6 0.2320(3) 0.41225(15) 0.70943(14) 0.0196(5) Uani d . . . 1 . .
O O4 0.1744(4) 0.5477(2) 0.56678(18) 0.0339(7) Uani d . . . 1 . .
H H4 0.2224 0.5255 0.529 0.051 Uiso calc U . R 1 . .
O O3 0.5701(3) 0.47175(18) 0.64129(14) 0.0231(5) Uani d . . . 1 . .
O O9 0.5213(4) 0.17926(17) 0.57531(16) 0.0282(6) Uani d . . . 1 . .
H H9 0.5924 0.2233 0.5709 0.042 Uiso calc U . R 1 . .
O O5 0.2063(3) 0.57452(16) 0.75700(14) 0.0195(5) Uani d . . . 1 . .
O O7 -0.1433(3) 0.5201(2) 0.81470(16) 0.0295(6) Uani d . . . 1 . .
O O009 0.7504(4) 0.31532(18) 0.55004(16) 0.0295(6) Uani d . . . 1 . .
H H009 0.7637 0.3686 0.5687 0.044 Uiso calc U . R 1 . .
O O8 -0.4134(4) 0.49720(17) 0.85329(17) 0.0319(7) Uani d . . . 1 . .
O O1 -0.0185(4) 0.79291(19) 0.92764(17) 0.0329(7) Uani d . . . 1 . .
H H1 -0.0968 0.7511 0.9278 0.049 Uiso calc U . R 1 . .
O O2 0.8197(4) 0.50295(17) 0.58785(17) 0.0332(7) Uani d . . . 1 . .
O O11 0.7242(4) 0.6640(2) 0.93479(19) 0.0442(8) Uani d . . . 1 . .
H H11 0.6928 0.6198 0.9038 0.066 Uiso calc U . R 1 . .
N N3 -0.0930(4) 0.3553(2) 0.76968(17) 0.0192(6) Uani d . . . 1 . .
N N1 0.5081(4) 0.63634(19) 0.68309(17) 0.0180(6) Uani d . . . 1 . .
O O10 0.2656(4) 0.4239(2) 0.88650(16) 0.0319(7) Uani d . . . 1 . .
C C27 0.0925(5) 0.2627(2) 0.6928(2) 0.0207(8) Uani d . . . 1 . .
C C17 -0.2756(5) 0.4686(3) 0.82561(19) 0.0226(7) Uani d . . . 1 . .
C C32 0.2315(5) 0.3258(2) 0.6820(2) 0.0177(7) Uani d . . . 1 . .
C C11 0.3697(5) 0.7180(2) 0.7838(2) 0.0218(8) Uani d . . . 1 . .
C C16 0.2270(5) 0.6559(2) 0.7950(2) 0.0184(7) Uani d . . . 1 . .
C C15 0.1021(5) 0.6810(2) 0.8459(2) 0.0215(8) Uani d . . . 1 . .
H H15 0.009 0.6391 0.8554 0.026 Uiso calc U . R 1 . .
C C6 0.7903(5) 0.7909(2) 0.6343(2) 0.0200(7) Uani d . . . 1 . .
C C31 0.3726(5) 0.2962(2) 0.6407(2) 0.0186(7) Uani d . . . 1 . .
H H31 0.4654 0.3384 0.6316 0.022 Uiso calc U . R 1 . .
C C28 0.1035(6) 0.1741(3) 0.6622(2) 0.0308(9) Uani d . . . 1 . .
H H28 0.0088 0.1319 0.6688 0.037 Uiso calc U . R 1 . .
C C19 -0.2543(6) 0.3107(3) 0.8844(2) 0.0271(9) Uani d . . . 1 . .
H H19A -0.142 0.3274 0.9222 0.032 Uiso calc U . R 1 . .
H H19B -0.3623 0.3271 0.9099 0.032 Uiso calc U . R 1 . .
C C13 0.2521(6) 0.8277(3) 0.8737(2) 0.0303(9) Uani d . . . 1 . .
H H13 0.261 0.8851 0.9004 0.036 Uiso calc U . R 1 . .
C C12 0.3772(6) 0.8027(3) 0.8247(2) 0.0283(9) Uani d . . . 1 . .
H H12 0.473 0.8443 0.8181 0.034 Uiso calc U . R 1 . .
C C30 0.3807(5) 0.2079(2) 0.6131(2) 0.0221(8) Uani d . . . 1 . .
C C10 0.5014(5) 0.7048(2) 0.7308(2) 0.0221(8) Uani d . . . 1 . .
H H10 0.5926 0.7508 0.7306 0.027 Uiso calc U . R 1 . .
C C7 0.8149(5) 0.6883(3) 0.6442(2) 0.0255(8) Uani d . . . 1 . .
H H7A 0.8738 0.676 0.7002 0.031 Uiso calc U . R 1 . .
H H7B 0.9017 0.6678 0.6084 0.031 Uiso calc U . R 1 . .
C C8 0.6416(5) 0.6299(2) 0.6266(2) 0.0193(7) Uani d . . . 1 . .
H H8 0.5753 0.6499 0.5729 0.023 Uiso calc U . R 1 . .
C C14 0.1121(5) 0.7662(3) 0.8829(2) 0.0249(8) Uani d . . . 1 . .
C C18 -0.2601(5) 0.3667(2) 0.8063(2) 0.0208(7) Uani d . . . 1 . .
H H18 -0.3698 0.3478 0.7668 0.025 Uiso calc U . R 1 . .
C C26 -0.0672(5) 0.2823(3) 0.7308(2) 0.0221(8) Uani d . . . 1 . .
H H26 -0.161 0.2371 0.7265 0.026 Uiso calc U . R 1 . .
C C9 0.6848(5) 0.5275(3) 0.61859(19) 0.0203(7) Uani d . . . 1 . .
C C5 0.6430(6) 0.8308(3) 0.5855(2) 0.0296(9) Uani d . . . 1 . .
H H5 0.5517 0.7931 0.5554 0.036 Uiso calc U . R 1 . .
C C3 0.7590(6) 0.9808(3) 0.6228(2) 0.0401(10) Uani d . . . 1 . .
H H3 0.7468 1.0454 0.62 0.048 Uiso calc U . R 1 . .
C C1 0.9245(6) 0.8469(3) 0.6761(2) 0.0284(9) Uani d . . . 1 . .
H H1A 1.0279 0.8206 0.7092 0.034 Uiso calc U . R 1 . .
C C4 0.6263(6) 0.9252(3) 0.5797(2) 0.0361(10) Uani d . . . 1 . .
H H4A 0.5239 0.9517 0.546 0.043 Uiso calc U . R 1 . .
C C20 -0.2546(6) 0.2087(3) 0.8704(2) 0.0280(9) Uani d . . . 1 . .
C C2 0.9084(6) 0.9415(3) 0.6698(3) 0.0387(10) Uani d . . . 1 . .
H H2 1.0017 0.9793 0.6984 0.046 Uiso calc U . R 1 . .
C C34 0.2526(6) 0.4541(4) 0.9658(2) 0.0443(11) Uani d . . . 1 . .
H H34A 0.2474 0.521 0.9667 0.067 Uiso calc U . R 1 . .
H H34B 0.3607 0.4331 1.003 0.067 Uiso calc U . R 1 . .
H H34C 0.1407 0.429 0.9824 0.067 Uiso calc U . R 1 . .
C C29 0.2441(6) 0.1450(3) 0.6231(2) 0.0328(10) Uani d . . . 1 . .
H H29 0.2478 0.0841 0.6037 0.039 Uiso calc U . R 1 . .
C C21 -0.4109(7) 0.1645(3) 0.8312(2) 0.0386(10) Uani d . . . 1 . .
H H21 -0.5209 0.1983 0.815 0.046 Uiso calc U . R 1 . .
C C35 0.8680(6) 0.3026(3) 0.4912(3) 0.0415(11) Uani d . . . 1 . .
H H35A 0.8258 0.3412 0.4443 0.062 Uiso calc U . R 1 . .
H H35B 0.8647 0.2383 0.4746 0.062 Uiso calc U . R 1 . .
H H35C 0.9944 0.3194 0.5142 0.062 Uiso calc U . R 1 . .
C C22 -0.4073(8) 0.0712(3) 0.8154(3) 0.0560(15) Uani d . . . 1 . .
H H22 -0.5142 0.0419 0.7878 0.067 Uiso calc U . R 1 . .
C C33 0.6037(6) 0.6698(4) 0.9929(3) 0.0481(12) Uani d . . . 1 . .
H H33A 0.6142 0.614 1.0256 0.072 Uiso calc U . R 1 . .
H H33B 0.4765 0.6766 0.9655 0.072 Uiso calc U . R 1 . .
H H33C 0.6373 0.7228 1.0277 0.072 Uiso calc U . R 1 . .
C C25 -0.0980(7) 0.1578(3) 0.8940(3) 0.0408(11) Uani d . . . 1 . .
H H25 0.01 0.1868 0.9209 0.049 Uiso calc U . R 1 . .
C C24 -0.0961(8) 0.0636(4) 0.8785(3) 0.0580(15) Uani d . . . 1 . .
H H24 0.0125 0.0289 0.8953 0.07 Uiso calc U . R 1 . .
C C23 -0.2508(9) 0.0218(4) 0.8393(3) 0.0614(15) Uani d . . . 1 . .
H H23 -0.2494 -0.0419 0.8286 0.074 Uiso calc U . R 1 . .
H H1W 0.088(7) 0.536(4) 0.569(3) 0.046(16) Uiso d . . . 1 . .
H H2W 0.368(8) 0.437(4) 0.871(3) 0.073(19) Uiso d . . . 1 . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cu1 N1 . 1.932(3) ?
Cu1 O3 . 1.936(2) ?
Cu1 O5 . 1.940(2) ?
Cu1 O6 . 1.996(2) ?
Cu1 O4 . 2.316(3) ?
Cu1 Cu2 . 3.0224(6) ?
Cu2 O7 . 1.932(2) ?
Cu2 N3 . 1.933(3) ?
Cu2 O6 . 1.939(2) ?
Cu2 O5 . 1.999(2) ?
Cu2 O10 . 2.290(3) ?
O6 C32 . 1.347(4) ?
O4 H4 . 0.84 ?
O4 H1W . 0.66(5) ?
O3 C9 . 1.274(4) ?
O9 C30 . 1.361(4) ?
O9 H9 . 0.84 ?
O5 C16 . 1.348(4) ?
O7 C17 . 1.267(4) ?
O009 C35 . 1.425(4) ?
O009 H009 . 0.84 ?
O8 C17 . 1.251(4) ?
O1 C14 . 1.367(4) ?
O1 H1 . 0.84 ?
O2 C9 . 1.241(4) ?
O11 C33 . 1.421(5) ?
O11 H11 . 0.84 ?
N3 C26 . 1.282(5) ?
N3 C18 . 1.467(4) ?
N1 C10 . 1.289(4) ?
N1 C8 . 1.472(4) ?
O10 C34 . 1.423(5) ?
O10 H2W . 0.86(5) ?
C27 C28 . 1.401(5) ?
C27 C32 . 1.409(5) ?
C27 C26 . 1.451(5) ?
C17 C18 . 1.533(5) ?
C32 C31 . 1.403(5) ?
C11 C12 . 1.415(5) ?
C11 C16 . 1.423(5) ?
C11 C10 . 1.428(5) ?
C16 C15 . 1.400(5) ?
C15 C14 . 1.390(5) ?
C15 H15 . 0.95 ?
C6 C5 . 1.381(5) ?
C6 C1 . 1.386(5) ?
C6 C7 . 1.519(5) ?
C31 C30 . 1.377(5) ?
C31 H31 . 0.95 ?
C28 C29 . 1.377(5) ?
C28 H28 . 0.95 ?
C19 C20 . 1.511(5) ?
C19 C18 . 1.543(5) ?
C19 H19A . 0.99 ?
C19 H19B . 0.99 ?
C13 C12 . 1.377(5) ?
C13 C14 . 1.393(5) ?
C13 H13 . 0.95 ?
C12 H12 . 0.95 ?
C30 C29 . 1.392(5) ?
C10 H10 . 0.95 ?
C7 C8 . 1.524(5) ?
C7 H7A . 0.99 ?
C7 H7B . 0.99 ?
C8 C9 . 1.541(5) ?
C8 H8 . 1.0 ?
C18 H18 . 1.0 ?
C26 H26 . 0.95 ?
C5 C4 . 1.390(5) ?
C5 H5 . 0.95 ?
C3 C2 . 1.375(6) ?
C3 C4 . 1.384(6) ?
C3 H3 . 0.95 ?
C1 C2 . 1.391(5) ?
C1 H1A . 0.95 ?
C4 H4A . 0.95 ?
C20 C25 . 1.375(6) ?
C20 C21 . 1.391(6) ?
C2 H2 . 0.95 ?
C34 H34A . 0.98 ?
C34 H34B . 0.98 ?
C34 H34C . 0.98 ?
C29 H29 . 0.95 ?
C21 C22 . 1.392(7) ?
C21 H21 . 0.95 ?
C35 H35A . 0.98 ?
C35 H35B . 0.98 ?
C35 H35C . 0.98 ?
C22 C23 . 1.365(8) ?
C22 H22 . 0.95 ?
C33 H33A . 0.98 ?
C33 H33B . 0.98 ?
C33 H33C . 0.98 ?
C25 C24 . 1.404(7) ?
C25 H25 . 0.95 ?
C24 C23 . 1.366(8) ?
C24 H24 . 0.95 ?
C23 H23 . 0.95 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
N1 Cu1 O3 . . 83.24(11) ?
N1 Cu1 O5 . . 94.98(11) ?
O3 Cu1 O5 . . 166.70(11) ?
N1 Cu1 O6 . . 171.59(11) ?
O3 Cu1 O6 . . 100.47(10) ?
O5 Cu1 O6 . . 79.66(9) ?
N1 Cu1 O4 . . 95.88(12) ?
O3 Cu1 O4 . . 96.38(11) ?
O5 Cu1 O4 . . 96.91(11) ?
O6 Cu1 O4 . . 91.21(11) ?
N1 Cu1 Cu2 . . 135.46(8) ?
O3 Cu1 Cu2 . . 138.62(8) ?
O5 Cu1 Cu2 . . 40.60(7) ?
O6 Cu1 Cu2 . . 39.12(6) ?
O4 Cu1 Cu2 . . 93.53(8) ?
O7 Cu2 N3 . . 83.45(12) ?
O7 Cu2 O6 . . 166.31(11) ?
N3 Cu2 O6 . . 95.28(11) ?
O7 Cu2 O5 . . 99.20(11) ?
N3 Cu2 O5 . . 169.18(11) ?
O6 Cu2 O5 . . 79.64(9) ?
O7 Cu2 O10 . . 105.45(11) ?
N3 Cu2 O10 . . 97.82(11) ?
O6 Cu2 O10 . . 88.23(11) ?
O5 Cu2 O10 . . 91.61(10) ?
O7 Cu2 Cu1 . . 136.20(9) ?
N3 Cu2 Cu1 . . 134.59(8) ?
O6 Cu2 Cu1 . . 40.52(7) ?
O5 Cu2 Cu1 . . 39.19(6) ?
O10 Cu2 Cu1 . . 91.62(7) ?
C32 O6 Cu2 . . 125.9(2) ?
C32 O6 Cu1 . . 133.3(2) ?
Cu2 O6 Cu1 . . 100.36(10) ?
Cu1 O4 H4 . . 109.5 ?
Cu1 O4 H1W . . 112.(4) ?
H4 O4 H1W . . 117.9 ?
C9 O3 Cu1 . . 116.4(2) ?
C30 O9 H9 . . 109.5 ?
C16 O5 Cu1 . . 125.6(2) ?
C16 O5 Cu2 . . 132.4(2) ?
Cu1 O5 Cu2 . . 100.21(10) ?
C17 O7 Cu2 . . 116.7(3) ?
C35 O009 H009 . . 109.5 ?
C14 O1 H1 . . 109.5 ?
C33 O11 H11 . . 109.5 ?
C26 N3 C18 . . 120.7(3) ?
C26 N3 Cu2 . . 124.6(2) ?
C18 N3 Cu2 . . 114.3(2) ?
C10 N1 C8 . . 123.1(3) ?
C10 N1 Cu1 . . 124.1(2) ?
C8 N1 Cu1 . . 112.4(2) ?
C34 O10 Cu2 . . 124.2(3) ?
C34 O10 H2W . . 114.(4) ?
Cu2 O10 H2W . . 101.(4) ?
C28 C27 C32 . . 118.3(3) ?
C28 C27 C26 . . 116.2(3) ?
C32 C27 C26 . . 125.4(3) ?
O8 C17 O7 . . 122.6(4) ?
O8 C17 C18 . . 119.8(3) ?
O7 C17 C18 . . 117.6(3) ?
O6 C32 C31 . . 119.8(3) ?
O6 C32 C27 . . 122.3(3) ?
C31 C32 C27 . . 118.0(3) ?
C12 C11 C16 . . 118.0(3) ?
C12 C11 C10 . . 116.3(3) ?
C16 C11 C10 . . 125.6(3) ?
O5 C16 C15 . . 119.1(3) ?
O5 C16 C11 . . 122.1(3) ?
C15 C16 C11 . . 118.8(3) ?
C14 C15 C16 . . 121.0(3) ?
C14 C15 H15 . . 119.5 ?
C16 C15 H15 . . 119.5 ?
C5 C6 C1 . . 118.8(3) ?
C5 C6 C7 . . 123.4(3) ?
C1 C6 C7 . . 117.8(3) ?
C30 C31 C32 . . 122.0(3) ?
C30 C31 H31 . . 119.0 ?
C32 C31 H31 . . 119.0 ?
C29 C28 C27 . . 123.5(4) ?
C29 C28 H28 . . 118.2 ?
C27 C28 H28 . . 118.2 ?
C20 C19 C18 . . 113.2(3) ?
C20 C19 H19A . . 108.9 ?
C18 C19 H19A . . 108.9 ?
C20 C19 H19B . . 108.9 ?
C18 C19 H19B . . 108.9 ?
H19A C19 H19B . . 107.8 ?
C12 C13 C14 . . 118.0(4) ?
C12 C13 H13 . . 121.0 ?
C14 C13 H13 . . 121.0 ?
C13 C12 C11 . . 123.0(4) ?
C13 C12 H12 . . 118.5 ?
C11 C12 H12 . . 118.5 ?
O9 C30 C31 . . 121.5(3) ?
O9 C30 C29 . . 117.8(3) ?
C31 C30 C29 . . 120.7(3) ?
N1 C10 C11 . . 126.1(3) ?
N1 C10 H10 . . 116.9 ?
C11 C10 H10 . . 116.9 ?
C6 C7 C8 . . 116.9(3) ?
C6 C7 H7A . . 108.1 ?
C8 C7 H7A . . 108.1 ?
C6 C7 H7B . . 108.1 ?
C8 C7 H7B . . 108.1 ?
H7A C7 H7B . . 107.3 ?
N1 C8 C7 . . 117.4(3) ?
N1 C8 C9 . . 106.6(3) ?
C7 C8 C9 . . 112.6(3) ?
N1 C8 H8 . . 106.5 ?
C7 C8 H8 . . 106.5 ?
C9 C8 H8 . . 106.5 ?
O1 C14 C15 . . 120.7(3) ?
O1 C14 C13 . . 118.1(3) ?
C15 C14 C13 . . 121.2(3) ?
N3 C18 C17 . . 107.2(3) ?
N3 C18 C19 . . 112.5(3) ?
C17 C18 C19 . . 109.2(3) ?
N3 C18 H18 . . 109.3 ?
C17 C18 H18 . . 109.3 ?
C19 C18 H18 . . 109.3 ?
N3 C26 C27 . . 125.8(3) ?
N3 C26 H26 . . 117.1 ?
C27 C26 H26 . . 117.1 ?
O2 C9 O3 . . 123.3(4) ?
O2 C9 C8 . . 120.5(3) ?
O3 C9 C8 . . 116.2(3) ?
C6 C5 C4 . . 120.9(4) ?
C6 C5 H5 . . 119.6 ?
C4 C5 H5 . . 119.6 ?
C2 C3 C4 . . 119.3(4) ?
C2 C3 H3 . . 120.4 ?
C4 C3 H3 . . 120.4 ?
C6 C1 C2 . . 120.3(4) ?
C6 C1 H1A . . 119.9 ?
C2 C1 H1A . . 119.9 ?
C3 C4 C5 . . 120.0(4) ?
C3 C4 H4A . . 120.0 ?
C5 C4 H4A . . 120.0 ?
C25 C20 C21 . . 118.5(4) ?
C25 C20 C19 . . 120.6(4) ?
C21 C20 C19 . . 120.9(4) ?
C3 C2 C1 . . 120.7(4) ?
C3 C2 H2 . . 119.7 ?
C1 C2 H2 . . 119.7 ?
O10 C34 H34A . . 109.5 ?
O10 C34 H34B . . 109.5 ?
H34A C34 H34B . . 109.5 ?
O10 C34 H34C . . 109.5 ?
H34A C34 H34C . . 109.5 ?
H34B C34 H34C . . 109.5 ?
C28 C29 C30 . . 117.5(3) ?
C28 C29 H29 . . 121.2 ?
C30 C29 H29 . . 121.2 ?
C20 C21 C22 . . 120.5(5) ?
C20 C21 H21 . . 119.8 ?
C22 C21 H21 . . 119.8 ?
O009 C35 H35A . . 109.5 ?
O009 C35 H35B . . 109.5 ?
H35A C35 H35B . . 109.5 ?
O009 C35 H35C . . 109.5 ?
H35A C35 H35C . . 109.5 ?
H35B C35 H35C . . 109.5 ?
C23 C22 C21 . . 120.3(6) ?
C23 C22 H22 . . 119.9 ?
C21 C22 H22 . . 119.9 ?
O11 C33 H33A . . 109.5 ?
O11 C33 H33B . . 109.5 ?
H33A C33 H33B . . 109.5 ?
O11 C33 H33C . . 109.5 ?
H33A C33 H33C . . 109.5 ?
H33B C33 H33C . . 109.5 ?
C20 C25 C24 . . 120.7(5) ?
C20 C25 H25 . . 119.7 ?
C24 C25 H25 . . 119.7 ?
C23 C24 C25 . . 119.8(5) ?
C23 C24 H24 . . 120.1 ?
C25 C24 H24 . . 120.1 ?
C22 C23 C24 . . 120.3(5) ?
C22 C23 H23 . . 119.9 ?
C24 C23 H23 . . 119.9 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
Cu2 O7 C17 O8 . . . . 178.1(3) ?
Cu2 O7 C17 C18 . . . . 0.2(4) ?
Cu2 O6 C32 C31 . . . . -174.9(2) ?
Cu1 O6 C32 C31 . . . . 14.3(5) ?
Cu2 O6 C32 C27 . . . . 5.3(5) ?
Cu1 O6 C32 C27 . . . . -165.4(3) ?
C28 C27 C32 O6 . . . . -179.9(3) ?
C26 C27 C32 O6 . . . . 2.5(6) ?
C28 C27 C32 C31 . . . . 0.3(5) ?
C26 C27 C32 C31 . . . . -177.3(3) ?
Cu1 O5 C16 C15 . . . . -177.5(2) ?
Cu2 O5 C16 C15 . . . . -15.9(5) ?
Cu1 O5 C16 C11 . . . . 3.9(5) ?
Cu2 O5 C16 C11 . . . . 165.5(3) ?
C12 C11 C16 O5 . . . . 178.4(3) ?
C10 C11 C16 O5 . . . . 2.2(6) ?
C12 C11 C16 C15 . . . . -0.3(5) ?
C10 C11 C16 C15 . . . . -176.4(4) ?
O5 C16 C15 C14 . . . . -176.4(3) ?
C11 C16 C15 C14 . . . . 2.3(5) ?
O6 C32 C31 C30 . . . . 178.5(3) ?
C27 C32 C31 C30 . . . . -1.8(5) ?
C32 C27 C28 C29 . . . . 0.9(6) ?
C26 C27 C28 C29 . . . . 178.7(4) ?
C14 C13 C12 C11 . . . . -0.1(6) ?
C16 C11 C12 C13 . . . . -0.8(6) ?
C10 C11 C12 C13 . . . . 175.7(4) ?
C32 C31 C30 O9 . . . . -178.0(3) ?
C32 C31 C30 C29 . . . . 2.0(6) ?
C8 N1 C10 C11 . . . . 176.3(4) ?
Cu1 N1 C10 C11 . . . . -12.2(5) ?
C12 C11 C10 N1 . . . . -173.8(4) ?
C16 C11 C10 N1 . . . . 2.4(6) ?
C5 C6 C7 C8 . . . . -23.8(5) ?
C1 C6 C7 C8 . . . . 156.9(3) ?
C10 N1 C8 C7 . . . . 20.8(5) ?
Cu1 N1 C8 C7 . . . . -151.6(3) ?
C10 N1 C8 C9 . . . . 148.1(3) ?
Cu1 N1 C8 C9 . . . . -24.2(3) ?
C6 C7 C8 N1 . . . . -69.3(4) ?
C6 C7 C8 C9 . . . . 166.4(3) ?
C16 C15 C14 O1 . . . . 175.1(3) ?
C16 C15 C14 C13 . . . . -3.2(6) ?
C12 C13 C14 O1 . . . . -176.2(3) ?
C12 C13 C14 C15 . . . . 2.1(6) ?
C26 N3 C18 C17 . . . . -163.8(3) ?
Cu2 N3 C18 C17 . . . . 9.1(3) ?
C26 N3 C18 C19 . . . . 76.2(4) ?
Cu2 N3 C18 C19 . . . . -111.0(3) ?
O8 C17 C18 N3 . . . . 175.9(3) ?
O7 C17 C18 N3 . . . . -6.1(4) ?
O8 C17 C18 C19 . . . . -61.9(4) ?
O7 C17 C18 C19 . . . . 116.1(3) ?
C20 C19 C18 N3 . . . . -65.8(4) ?
C20 C19 C18 C17 . . . . 175.3(3) ?
C18 N3 C26 C27 . . . . -179.3(3) ?
Cu2 N3 C26 C27 . . . . 8.5(5) ?
C28 C27 C26 N3 . . . . 172.2(4) ?
C32 C27 C26 N3 . . . . -10.2(6) ?
Cu1 O3 C9 O2 . . . . -179.8(3) ?
Cu1 O3 C9 C8 . . . . -3.4(4) ?
N1 C8 C9 O2 . . . . -165.4(3) ?
C7 C8 C9 O2 . . . . -35.3(5) ?
N1 C8 C9 O3 . . . . 18.0(4) ?
C7 C8 C9 O3 . . . . 148.2(3) ?
C1 C6 C5 C4 . . . . -1.6(6) ?
C7 C6 C5 C4 . . . . 179.1(4) ?
C5 C6 C1 C2 . . . . 1.1(6) ?
C7 C6 C1 C2 . . . . -179.5(4) ?
C2 C3 C4 C5 . . . . 1.4(6) ?
C6 C5 C4 C3 . . . . 0.3(6) ?
C18 C19 C20 C25 . . . . 107.8(4) ?
C18 C19 C20 C21 . . . . -70.0(5) ?
C4 C3 C2 C1 . . . . -1.8(7) ?
C6 C1 C2 C3 . . . . 0.6(7) ?
C27 C28 C29 C30 . . . . -0.7(6) ?
O9 C30 C29 C28 . . . . 179.2(3) ?
C31 C30 C29 C28 . . . . -0.8(6) ?
C25 C20 C21 C22 . . . . -0.8(6) ?
C19 C20 C21 C22 . . . . 177.1(4) ?
C20 C21 C22 C23 . . . . 0.9(7) ?
C21 C20 C25 C24 . . . . 0.2(6) ?
C19 C20 C25 C24 . . . . -177.8(4) ?
C20 C25 C24 C23 . . . . 0.4(7) ?
C21 C22 C23 C24 . . . . -0.4(7) ?
C25 C24 C23 C22 . . . . -0.3(7) ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O9 H9 O009 . 0.84 1.85 2.684(4) 173.7 ?
O009 H009 O3 . 0.84 2.52 3.161(3) 134.1 ?
O009 H009 O2 . 0.84 2.02 2.846(4) 165.8 ?
O1 H1 O11 1_455 0.84 1.85 2.687(4) 175.3 ?
O11 H11 O7 1_655 0.84 2.53 3.174(4) 134.6 ?
O11 H11 O8 1_655 0.84 2.08 2.902(4) 164.8 ?
C15 H15 O7 . 0.95 2.12 2.961(5) 146.2 ?
C31 H31 O3 . 0.95 2.09 2.949(4) 149.0 ?
C8 H8 O9 2_656 1.0 2.52 3.495(5) 164.7 ?
O4 H1W O2 1_455 0.66(5) 2.10(4) 2.764(4) 175.(6) ?
O10 H2W O8 1_655 0.86(5) 1.90(6) 2.728(4) 164.(5) ?

