# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_L
_database_code_depnum_ccdc_archive 'CCDC 1569983'
_audit_update_record             
;
2017-08-21 deposited with the CCDC.
2018-08-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H22 N2 O3'
_chemical_formula_weight         326.38

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P c'
_space_group_name_Hall           'P -2yc'

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

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

_cell_length_a                   16.4048(13)
_cell_length_b                   6.0674(5)
_cell_length_c                   8.3490(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.077(7)
_cell_angle_gamma                90
_cell_volume                     830.87(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    130(1)
_cell_measurement_reflns_used    1792
_cell_measurement_theta_min      5.2910
_cell_measurement_theta_max      74.5060

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_F_000             348
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.717
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.64766
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      130(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.5357
_diffrn_measurement_method       '/w scan'
_diffrn_reflns_number            2741
_diffrn_reflns_av_unetI/netI     0.0171
_diffrn_reflns_av_R_equivalents  0.0125
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.694
_diffrn_reflns_theta_max         75.236
_diffrn_reflns_theta_full        67.500
_diffrn_measured_fraction_theta_max 0.961
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.605
_diffrn_reflns_point_group_measured_fraction_full 0.635
_reflns_number_total             2084
_reflns_number_gt                2052
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.256
_reflns_Friedel_fraction_max     0.247
_reflns_Friedel_fraction_full    0.273

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

_computing_data_collection       'CrysAlisPro 1.171.38.34a (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.34a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.34a (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0681P)²+0.1199P] 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_abs_structure_details 
;
 Flack x determined using 405 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.4(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2084
_refine_ls_number_parameters     231
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.0969
_refine_ls_wR_factor_gt          0.0960
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.50106(13) 0.2849(4) 0.6257(3) 0.0274(5) Uani 1 1 d . . . . .
H1 H 0.5332 0.4171 0.6611 0.024 Uiso 1 1 d R U . . .
O1 O 0.45840(10) 0.2144(3) 0.7633(2) 0.0311(4) Uani 1 1 d . . . . .
H1O H 0.421(2) 0.092(7) 0.729(5) 0.062(11) Uiso 1 1 d . . . . .
C2 C 0.56136(13) 0.1091(4) 0.5717(3) 0.0310(5) Uani 1 1 d . . . . .
H2A H 0.5307 -0.0060 0.5185 0.041 Uiso 1 1 d R U . . .
H2B H 0.5918 0.0496 0.6623 0.035 Uiso 1 1 d R U . . .
N3 N 0.62018(11) 0.2039(3) 0.4623(2) 0.0289(4) Uani 1 1 d . . . . .
C4 C 0.68253(14) 0.0898(4) 0.4266(3) 0.0279(5) Uani 1 1 d . . . . .
H4 H 0.6908 -0.0649 0.4672 0.028 Uiso 1 1 d R U . . .
C5 C 0.74434(13) 0.1750(4) 0.3191(3) 0.0269(5) Uani 1 1 d . . . . .
C6 C 0.73883(13) 0.3903(4) 0.2561(3) 0.0282(5) Uani 1 1 d . . . . .
O6 O 0.67692(11) 0.5269(3) 0.2942(2) 0.0346(4) Uani 1 1 d . . . . .
H6 H 0.642(2) 0.452(7) 0.359(5) 0.054(10) Uiso 1 1 d . . . . .
C7 C 0.79847(14) 0.4642(4) 0.1522(3) 0.0317(5) Uani 1 1 d . . . . .
H7 H 0.7938 0.6064 0.1143 0.030 Uiso 1 1 d R U . . .
C8 C 0.86343(14) 0.3299(4) 0.1146(3) 0.0324(5) Uani 1 1 d . . . . .
H8 H 0.9058 0.3823 0.0448 0.041 Uiso 1 1 d R U . . .
C9 C 0.87130(14) 0.1165(4) 0.1781(3) 0.0312(5) Uani 1 1 d . . . . .
C91 C 0.94256(16) -0.0289(5) 0.1356(4) 0.0413(6) Uani 1 1 d . . . . .
H91A H 0.9362 -0.0787 0.0244 0.062 Uiso 1 1 calc R U . . .
H91B H 0.9442 -0.1571 0.2070 0.062 Uiso 1 1 calc R U . . .
H91C H 0.9934 0.0547 0.1479 0.062 Uiso 1 1 calc R U . . .
C10 C 0.81102(14) 0.0428(4) 0.2792(3) 0.0300(5) Uani 1 1 d . . . . .
H10 H 0.8145 -0.1081 0.3263 0.027 Uiso 1 1 d R U . . .
C11 C 0.44275(13) 0.3453(4) 0.4875(3) 0.0289(5) Uani 1 1 d . . . . .
H11A H 0.4101 0.2093 0.4585 0.037 Uiso 1 1 d R U . . .
H11B H 0.4723 0.4055 0.3987 0.037 Uiso 1 1 d R U . . .
N12 N 0.38432(12) 0.5101(3) 0.5387(2) 0.0282(4) Uani 1 1 d . . . . .
H12 H 0.396(2) 0.655(6) 0.554(4) 0.045(9) Uiso 1 1 d . . . . .
C13 C 0.31292(13) 0.4594(4) 0.5925(3) 0.0279(5) Uani 1 1 d . . . . .
H13 H 0.2986 0.3067 0.5809 0.023 Uiso 1 1 d R U . . .
C14 C 0.26111(13) 0.6117(4) 0.6706(3) 0.0273(5) Uani 1 1 d . . . . .
C15 C 0.28876(13) 0.8305(4) 0.7071(3) 0.0280(5) Uani 1 1 d . . . . .
O15 O 0.35644(10) 0.9042(3) 0.6529(2) 0.0324(4) Uani 1 1 d . . . . .
C16 C 0.23737(15) 0.9563(4) 0.8089(3) 0.0329(5) Uani 1 1 d . . . . .
H16 H 0.2543 1.0989 0.8404 0.029 Uiso 1 1 d R U . . .
C17 C 0.16487(15) 0.8747(4) 0.8620(3) 0.0329(5) Uani 1 1 d . . . . .
H17 H 0.1334 0.9652 0.9341 0.038 Uiso 1 1 d R U . . .
C18 C 0.13655(13) 0.6610(4) 0.8222(3) 0.0318(5) Uani 1 1 d . . . . .
C181 C 0.05696(15) 0.5727(5) 0.8848(3) 0.0394(6) Uani 1 1 d . . . . .
H18A H 0.0546 0.4129 0.8681 0.059 Uiso 1 1 calc R U . . .
H18B H 0.0113 0.6431 0.8274 0.059 Uiso 1 1 calc R U . . .
H18C H 0.0535 0.6048 0.9995 0.059 Uiso 1 1 calc R U . . .
C19 C 0.18563(14) 0.5341(4) 0.7282(3) 0.0299(5) Uani 1 1 d . . . . .
H19 H 0.1708 0.3869 0.7067 0.033 Uiso 1 1 d R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.422(3) . ?
C1 C2 1.529(3) . ?
C1 C11 1.530(3) . ?
C1 H1 1.0009 . ?
O1 H1O 1.00(4) . ?
C2 N3 1.460(3) . ?
C2 H2A 0.9642 . ?
C2 H2B 0.9679 . ?
N3 C4 1.275(3) . ?
C4 C5 1.461(3) . ?
C4 H4 1.0059 . ?
C5 C10 1.402(3) . ?
C5 C6 1.411(3) . ?
C6 O6 1.353(3) . ?
C6 C7 1.394(3) . ?
O6 H6 0.91(4) . ?
C7 C8 1.382(3) . ?
C7 H7 0.9217 . ?
C8 C9 1.404(4) . ?
C8 H8 0.9692 . ?
C9 C10 1.386(3) . ?
C9 C91 1.512(3) . ?
C91 H91A 0.9800 . ?
C91 H91B 0.9800 . ?
C91 H91C 0.9800 . ?
C10 H10 0.9979 . ?
C11 N12 1.455(3) . ?
C11 H11A 1.0105 . ?
C11 H11B 0.9651 . ?
N12 C13 1.299(3) . ?
N12 H12 0.91(4) . ?
C13 C14 1.422(3) . ?
C13 H13 0.9602 . ?
C14 C19 1.417(3) . ?
C14 C15 1.434(3) . ?
C15 O15 1.287(3) . ?
C15 C16 1.429(3) . ?
C16 C17 1.370(4) . ?
C16 H16 0.9444 . ?
C17 C18 1.415(4) . ?
C17 H17 0.9706 . ?
C18 C19 1.371(3) . ?
C18 C181 1.514(3) . ?
C181 H18A 0.9800 . ?
C181 H18B 0.9800 . ?
C181 H18C 0.9800 . ?
C19 H19 0.9423 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 111.06(18) . . ?
O1 C1 C11 111.80(17) . . ?
C2 C1 C11 110.07(19) . . ?
O1 C1 H1 105.5 . . ?
C2 C1 H1 107.8 . . ?
C11 C1 H1 110.4 . . ?
C1 O1 H1O 107(2) . . ?
N3 C2 C1 110.40(18) . . ?
N3 C2 H2A 110.0 . . ?
C1 C2 H2A 107.9 . . ?
N3 C2 H2B 107.4 . . ?
C1 C2 H2B 110.9 . . ?
H2A C2 H2B 110.3 . . ?
C4 N3 C2 118.33(19) . . ?
N3 C4 C5 121.3(2) . . ?
N3 C4 H4 122.1 . . ?
C5 C4 H4 116.5 . . ?
C10 C5 C6 119.1(2) . . ?
C10 C5 C4 119.8(2) . . ?
C6 C5 C4 121.1(2) . . ?
O6 C6 C7 119.2(2) . . ?
O6 C6 C5 121.5(2) . . ?
C7 C6 C5 119.3(2) . . ?
C6 O6 H6 108(2) . . ?
C8 C7 C6 120.3(2) . . ?
C8 C7 H7 122.2 . . ?
C6 C7 H7 117.4 . . ?
C7 C8 C9 121.6(2) . . ?
C7 C8 H8 120.5 . . ?
C9 C8 H8 117.9 . . ?
C10 C9 C8 117.8(2) . . ?
C10 C9 C91 121.2(2) . . ?
C8 C9 C91 121.0(2) . . ?
C9 C91 H91A 109.5 . . ?
C9 C91 H91B 109.5 . . ?
H91A C91 H91B 109.5 . . ?
C9 C91 H91C 109.5 . . ?
H91A C91 H91C 109.5 . . ?
H91B C91 H91C 109.5 . . ?
C9 C10 C5 121.9(2) . . ?
C9 C10 H10 120.0 . . ?
C5 C10 H10 118.1 . . ?
N12 C11 C1 110.42(18) . . ?
N12 C11 H11A 106.4 . . ?
C1 C11 H11A 107.8 . . ?
N12 C11 H11B 107.9 . . ?
C1 C11 H11B 110.8 . . ?
H11A C11 H11B 113.3 . . ?
C13 N12 C11 122.81(19) . . ?
C13 N12 H12 112(2) . . ?
C11 N12 H12 125(2) . . ?
N12 C13 C14 123.7(2) . . ?
N12 C13 H13 114.5 . . ?
C14 C13 H13 121.7 . . ?
C19 C14 C13 118.2(2) . . ?
C19 C14 C15 120.7(2) . . ?
C13 C14 C15 120.6(2) . . ?
O15 C15 C16 123.1(2) . . ?
O15 C15 C14 121.2(2) . . ?
C16 C15 C14 115.7(2) . . ?
C17 C16 C15 121.7(2) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 118.7 . . ?
C16 C17 C18 122.6(2) . . ?
C16 C17 H17 118.1 . . ?
C18 C17 H17 119.2 . . ?
C19 C18 C17 117.1(2) . . ?
C19 C18 C181 121.2(2) . . ?
C17 C18 C181 121.7(2) . . ?
C18 C181 H18A 109.5 . . ?
C18 C181 H18B 109.5 . . ?
H18A C181 H18B 109.5 . . ?
C18 C181 H18C 109.5 . . ?
H18A C181 H18C 109.5 . . ?
H18B C181 H18C 109.5 . . ?
C18 C19 C14 122.3(2) . . ?
C18 C19 H19 119.3 . . ?
C14 C19 H19 118.4 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 N3 -163.85(18) . . . . ?
C11 C1 C2 N3 71.8(2) . . . . ?
C1 C2 N3 C4 168.6(2) . . . . ?
C2 N3 C4 C5 -179.39(19) . . . . ?
N3 C4 C5 C10 -178.3(2) . . . . ?
N3 C4 C5 C6 2.6(3) . . . . ?
C10 C5 C6 O6 -178.2(2) . . . . ?
C4 C5 C6 O6 0.8(3) . . . . ?
C10 C5 C6 C7 1.8(3) . . . . ?
C4 C5 C6 C7 -179.1(2) . . . . ?
O6 C6 C7 C8 178.4(2) . . . . ?
C5 C6 C7 C8 -1.7(4) . . . . ?
C6 C7 C8 C9 0.4(4) . . . . ?
C7 C8 C9 C10 0.7(4) . . . . ?
C7 C8 C9 C91 179.8(2) . . . . ?
C8 C9 C10 C5 -0.5(4) . . . . ?
C91 C9 C10 C5 -179.7(2) . . . . ?
C6 C5 C10 C9 -0.7(3) . . . . ?
C4 C5 C10 C9 -179.8(2) . . . . ?
O1 C1 C11 N12 55.2(2) . . . . ?
C2 C1 C11 N12 179.10(17) . . . . ?
C1 C11 N12 C13 -93.5(3) . . . . ?
C11 N12 C13 C14 167.8(2) . . . . ?
N12 C13 C14 C19 -178.1(2) . . . . ?
N12 C13 C14 C15 -5.5(3) . . . . ?
C19 C14 C15 O15 -178.7(2) . . . . ?
C13 C14 C15 O15 8.9(3) . . . . ?
C19 C14 C15 C16 2.6(3) . . . . ?
C13 C14 C15 C16 -169.8(2) . . . . ?
O15 C15 C16 C17 178.7(2) . . . . ?
C14 C15 C16 C17 -2.6(3) . . . . ?
C15 C16 C17 C18 0.9(4) . . . . ?
C16 C17 C18 C19 0.9(4) . . . . ?
C16 C17 C18 C181 178.8(2) . . . . ?
C17 C18 C19 C14 -0.8(4) . . . . ?
C181 C18 C19 C14 -178.8(2) . . . . ?
C13 C14 C19 C18 171.6(2) . . . . ?
C15 C14 C19 C18 -1.0(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1O O15 1.00(4) 1.67(4) 2.671(2) 174(4) 1_545
O6 H6 N3 0.91(4) 1.78(4) 2.593(3) 148(4) .
N12 H12 O15 0.91(4) 1.84(4) 2.617(3) 142(3) .

_refine_diff_density_max         0.165
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.041

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_L1
_database_code_depnum_ccdc_archive 'CCDC 1569984'
_audit_update_record             
;
2017-08-21 deposited with the CCDC.
2018-08-20 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H22 N2 O3'
_chemical_formula_sum            'C19 H22 N2 O3'
_chemical_formula_weight         326.38

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

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

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

_cell_length_a                   9.396(2)
_cell_length_b                   37.076(8)
_cell_length_c                   9.9611(16)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3470.1(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    948
_cell_measurement_theta_min      3.6770
_cell_measurement_theta_max      21.5620

_exptl_crystal_description       plate
_exptl_crystal_colour            pale-yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.249
_exptl_crystal_F_000             1392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.085
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.71676
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      295(2)
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.1544
_diffrn_measurement_method       '/w scan'
_diffrn_reflns_number            13285
_diffrn_reflns_av_unetI/netI     0.1190
_diffrn_reflns_av_R_equivalents  0.0916
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -44
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.031
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3049
_reflns_number_gt                1318
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.38.34a (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.34a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.34a (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0785P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3049
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2045
_refine_ls_R_factor_gt           0.0876
_refine_ls_wR_factor_ref         0.2136
_refine_ls_wR_factor_gt          0.1727
_refine_ls_goodness_of_fit_ref   0.982
_refine_ls_restrained_S_all      0.982
_refine_ls_shift/su_max          0.046
_refine_ls_shift/su_mean         0.011

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 0.1882(5) 0.48933(12) 0.6288(4) 0.0570(13) Uani 1 1 d . . . . .
H1 H 0.1904 0.4862 0.5311 0.068 Uiso 1 1 calc R U . . .
O1 O 0.3234(4) 0.48077(10) 0.6854(3) 0.0871(12) Uani 1 1 d . . . . .
H1A H 0.3692 0.4686 0.6319 0.105 Uiso 1 1 calc R U . . .
C2 C 0.1628(5) 0.52796(12) 0.6637(4) 0.0678(15) Uani 1 1 d . . . . .
H2A H 0.0643 0.5341 0.6458 0.081 Uiso 1 1 calc R U . . .
H2B H 0.1805 0.5316 0.7586 0.081 Uiso 1 1 calc R U . . .
N3 N 0.2552(5) 0.55130(11) 0.5861(3) 0.0568(11) Uani 1 1 d . . . . .
H3 H 0.351(6) 0.5419(14) 0.544(5) 0.12(2) Uiso 1 1 d . . . . .
C4 C 0.2192(5) 0.58304(13) 0.5510(4) 0.0605(13) Uani 1 1 d . . . . .
H4 H 0.1315 0.5921 0.5781 0.073 Uiso 1 1 calc R U . . .
C5 C 0.3101(5) 0.60496(12) 0.4715(4) 0.0517(12) Uani 1 1 d . . . . .
O6 O 0.4857(3) 0.55882(9) 0.4571(3) 0.0612(9) Uani 1 1 d . . . . .
C6 C 0.4400(5) 0.59134(13) 0.4244(4) 0.0520(12) Uani 1 1 d . . . . .
C7 C 0.5222(6) 0.61330(16) 0.3428(4) 0.0692(15) Uani 1 1 d . . . . .
H7 H 0.6084 0.6049 0.3093 0.083 Uiso 1 1 calc R U . . .
C8 C 0.4769(7) 0.64721(17) 0.3115(5) 0.0772(17) Uani 1 1 d . . . . .
H8 H 0.5347 0.6615 0.2576 0.093 Uiso 1 1 calc R U . . .
C9 C 0.3492(6) 0.66131(15) 0.3560(5) 0.0741(15) Uani 1 1 d . . . . .
C91 C 0.3019(7) 0.69876(15) 0.3175(6) 0.117(2) Uani 1 1 d . . . . .
H91A H 0.2647 0.6984 0.2277 0.175 Uiso 1 1 calc R U . . .
H91B H 0.3816 0.7149 0.3218 0.175 Uiso 1 1 calc R U . . .
H91C H 0.2293 0.7068 0.3784 0.175 Uiso 1 1 calc R U . . .
C10 C 0.2675(5) 0.63951(13) 0.4364(5) 0.0679(14) Uani 1 1 d . . . . .
H10 H 0.1810 0.6482 0.4683 0.081 Uiso 1 1 calc R U . . .
C11 C 0.0775(5) 0.46538(12) 0.6895(4) 0.0650(14) Uani 1 1 d . . . . .
H11A H 0.0833 0.4667 0.7866 0.078 Uiso 1 1 calc R U . . .
H11B H -0.0163 0.4736 0.6627 0.078 Uiso 1 1 calc R U . . .
N12 N 0.0973(4) 0.42861(10) 0.6469(3) 0.0566(11) Uani 1 1 d . . . . .
C13 C 0.0840(5) 0.40341(12) 0.7325(4) 0.0538(12) Uani 1 1 d . . . . .
H13 H 0.0650 0.4096 0.8212 0.065 Uiso 1 1 calc R U . . .
C14 C 0.0967(5) 0.36602(11) 0.6993(4) 0.0493(12) Uani 1 1 d . . . . .
O15 O 0.1538(4) 0.37956(10) 0.4711(3) 0.0713(11) Uani 1 1 d . . . . .
H15 H 0.134(5) 0.4010(13) 0.509(4) 0.087(18) Uiso 1 1 d . . . . .
C15 C 0.1302(5) 0.35541(13) 0.5684(4) 0.0531(12) Uani 1 1 d . . . . .
C16 C 0.1399(5) 0.31950(14) 0.5397(4) 0.0694(15) Uani 1 1 d . . . . .
H16 H 0.1632 0.3123 0.4530 0.083 Uiso 1 1 calc R U . . .
C17 C 0.1161(5) 0.29395(13) 0.6357(5) 0.0696(15) Uani 1 1 d . . . . .
H17 H 0.1239 0.2697 0.6132 0.083 Uiso 1 1 calc R U . . .
C18 C 0.0804(5) 0.30351(13) 0.7666(4) 0.0626(14) Uani 1 1 d . . . . .
C181 C 0.0510(6) 0.27548(13) 0.8718(5) 0.0912(18) Uani 1 1 d . . . . .
H18A H 0.0868 0.2836 0.9568 0.137 Uiso 1 1 calc R U . . .
H18B H 0.0973 0.2533 0.8475 0.137 Uiso 1 1 calc R U . . .
H18C H -0.0497 0.2716 0.8783 0.137 Uiso 1 1 calc R U . . .
C19 C 0.0729(5) 0.33972(12) 0.7953(4) 0.0600(13) Uani 1 1 d . . . . .
H19 H 0.0511 0.3468 0.8825 0.072 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.426(5) . ?
C1 C2 1.493(6) . ?
C1 C11 1.495(6) . ?
C1 H1 0.9800 . ?
O1 H1A 0.8200 . ?
C2 N3 1.449(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
N3 C4 1.273(5) . ?
N3 H3 1.05(6) . ?
C4 C5 1.420(6) . ?
C4 H4 0.9300 . ?
C5 C10 1.387(6) . ?
C5 C6 1.402(6) . ?
O6 C6 1.320(5) . ?
C6 C7 1.386(6) . ?
C7 C8 1.364(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.381(7) . ?
C8 H8 0.9300 . ?
C9 C10 1.373(6) . ?
C9 C91 1.508(7) . ?
C91 H91A 0.9600 . ?
C91 H91B 0.9600 . ?
C91 H91C 0.9600 . ?
C10 H10 0.9300 . ?
C11 N12 1.440(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
N12 C13 1.271(5) . ?
C13 C14 1.430(5) . ?
C13 H13 0.9300 . ?
C14 C19 1.384(5) . ?
C14 C15 1.398(5) . ?
O15 C15 1.338(5) . ?
O15 H15 0.90(5) . ?
C15 C16 1.365(6) . ?
C16 C17 1.365(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.392(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.375(6) . ?
C18 C181 1.501(6) . ?
C181 H18A 0.9600 . ?
C181 H18B 0.9600 . ?
C181 H18C 0.9600 . ?
C19 H19 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 105.3(4) . . ?
O1 C1 C11 109.1(4) . . ?
C2 C1 C11 111.4(4) . . ?
O1 C1 H1 110.3 . . ?
C2 C1 H1 110.3 . . ?
C11 C1 H1 110.3 . . ?
C1 O1 H1A 109.5 . . ?
N3 C2 C1 110.7(4) . . ?
N3 C2 H2A 109.5 . . ?
C1 C2 H2A 109.5 . . ?
N3 C2 H2B 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C4 N3 C2 122.7(4) . . ?
C4 N3 H3 115(3) . . ?
C2 N3 H3 122(3) . . ?
N3 C4 C5 121.5(5) . . ?
N3 C4 H4 119.2 . . ?
C5 C4 H4 119.3 . . ?
C10 C5 C6 120.0(5) . . ?
C10 C5 C4 119.7(5) . . ?
C6 C5 C4 120.3(4) . . ?
O6 C6 C7 120.0(5) . . ?
O6 C6 C5 122.0(4) . . ?
C7 C6 C5 118.0(5) . . ?
C8 C7 C6 120.1(5) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C9 123.1(5) . . ?
C7 C8 H8 118.4 . . ?
C9 C8 H8 118.4 . . ?
C10 C9 C8 116.8(5) . . ?
C10 C9 C91 121.7(6) . . ?
C8 C9 C91 121.5(6) . . ?
C9 C91 H91A 109.5 . . ?
C9 C91 H91B 109.5 . . ?
H91A C91 H91B 109.5 . . ?
C9 C91 H91C 109.5 . . ?
H91A C91 H91C 109.5 . . ?
H91B C91 H91C 109.5 . . ?
C9 C10 C5 122.0(5) . . ?
C9 C10 H10 119.0 . . ?
C5 C10 H10 119.0 . . ?
N12 C11 C1 110.7(4) . . ?
N12 C11 H11A 109.5 . . ?
C1 C11 H11A 109.5 . . ?
N12 C11 H11B 109.5 . . ?
C1 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
C13 N12 C11 119.0(4) . . ?
N12 C13 C14 123.3(4) . . ?
N12 C13 H13 118.4 . . ?
C14 C13 H13 118.4 . . ?
C19 C14 C15 118.9(4) . . ?
C19 C14 C13 120.6(4) . . ?
C15 C14 C13 120.5(4) . . ?
C15 O15 H15 104(3) . . ?
O15 C15 C16 119.3(4) . . ?
O15 C15 C14 121.6(4) . . ?
C16 C15 C14 119.0(4) . . ?
C17 C16 C15 121.3(4) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 H16 119.3 . . ?
C16 C17 C18 121.3(4) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C19 C18 C17 117.1(4) . . ?
C19 C18 C181 121.4(4) . . ?
C17 C18 C181 121.5(5) . . ?
C18 C181 H18A 109.5 . . ?
C18 C181 H18B 109.5 . . ?
H18A C181 H18B 109.5 . . ?
C18 C181 H18C 109.5 . . ?
H18A C181 H18C 109.5 . . ?
H18B C181 H18C 109.5 . . ?
C18 C19 C14 122.4(4) . . ?
C18 C19 H19 118.8 . . ?
C14 C19 H19 118.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 N3 71.7(5) . . . . ?
C11 C1 C2 N3 -170.1(4) . . . . ?
C1 C2 N3 C4 148.9(4) . . . . ?
C2 N3 C4 C5 -178.1(4) . . . . ?
N3 C4 C5 C10 -179.5(4) . . . . ?
N3 C4 C5 C6 2.9(7) . . . . ?
C10 C5 C6 O6 178.9(4) . . . . ?
C4 C5 C6 O6 -3.4(6) . . . . ?
C10 C5 C6 C7 -0.2(6) . . . . ?
C4 C5 C6 C7 177.5(4) . . . . ?
O6 C6 C7 C8 -178.5(4) . . . . ?
C5 C6 C7 C8 0.7(6) . . . . ?
C6 C7 C8 C9 -0.9(7) . . . . ?
C7 C8 C9 C10 0.7(8) . . . . ?
C7 C8 C9 C91 -179.1(5) . . . . ?
C8 C9 C10 C5 -0.1(7) . . . . ?
C91 C9 C10 C5 179.6(5) . . . . ?
C6 C5 C10 C9 -0.1(7) . . . . ?
C4 C5 C10 C9 -177.7(4) . . . . ?
O1 C1 C11 N12 -68.4(5) . . . . ?
C2 C1 C11 N12 175.8(4) . . . . ?
C1 C11 N12 C13 137.7(5) . . . . ?
C11 N12 C13 C14 177.8(4) . . . . ?
N12 C13 C14 C19 -176.2(5) . . . . ?
N12 C13 C14 C15 2.3(7) . . . . ?
C19 C14 C15 O15 179.8(4) . . . . ?
C13 C14 C15 O15 1.3(7) . . . . ?
C19 C14 C15 C16 -0.7(7) . . . . ?
C13 C14 C15 C16 -179.2(4) . . . . ?
O15 C15 C16 C17 -179.7(4) . . . . ?
C14 C15 C16 C17 0.7(8) . . . . ?
C15 C16 C17 C18 0.3(8) . . . . ?
C16 C17 C18 C19 -1.2(8) . . . . ?
C16 C17 C18 C181 178.7(5) . . . . ?
C17 C18 C19 C14 1.2(8) . . . . ?
C181 C18 C19 C14 -178.7(5) . . . . ?
C15 C14 C19 C18 -0.3(8) . . . . ?
C13 C14 C19 C18 178.2(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1A O6 0.82 1.92 2.718(4) 164.8 5_666
N3 H3 O6 1.05(6) 1.66(6) 2.534(5) 137(4) .
O15 H15 N12 0.90(5) 1.74(5) 2.580(5) 153(4) .

_refine_diff_density_max         0.219
_refine_diff_density_min         -0.213
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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 1569985'
_audit_update_record             
;
2017-08-21 deposited with the CCDC.
2018-08-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H26 Cu2 N2 O6, C H4 O'
_chemical_formula_sum            'C23 H30 Cu2 N2 O7'
_chemical_formula_weight         573.57

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

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

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

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

_cell_length_a                   15.4733(4)
_cell_length_b                   9.9490(2)
_cell_length_c                   15.8181(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.548(3)
_cell_angle_gamma                90
_cell_volume                     2401.37(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(1)
_cell_measurement_reflns_used    3602
_cell_measurement_theta_min      3.3640
_cell_measurement_theta_max      26.3420

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    1.817
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.80785
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      130(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.2413
_diffrn_measurement_method       '/w scan'
_diffrn_reflns_number            9312
_diffrn_reflns_av_unetI/netI     0.0317
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.319
_diffrn_reflns_theta_max         26.498
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4604
_reflns_number_gt                3958
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.38.34a (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.34a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.34a (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0337P)²+0.8695P] 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         4604
_refine_ls_number_parameters     314
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0299
_refine_ls_wR_factor_ref         0.0761
_refine_ls_wR_factor_gt          0.0716
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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
Cu1 Cu 0.24777(2) 0.35898(3) 0.86609(2) 0.02274(9) Uani 1 1 d . . . . .
Cu2 Cu 0.47699(2) 0.37787(3) 0.88993(2) 0.02234(9) Uani 1 1 d . . . . .
C1A C 0.35452(16) 0.5758(2) 0.83268(16) 0.0278(5) Uani 1 1 d . . . . .
H1A H 0.3613 0.5667 0.7712 0.033 Uiso 1 1 calc R U . . .
O1A O 0.35846(10) 0.44403(16) 0.87033(10) 0.0247(4) Uani 1 1 d . . . . .
C2A C 0.26613(16) 0.6373(2) 0.83640(17) 0.0294(6) Uani 1 1 d . . . . .
H2A1 H 0.2666 0.6813 0.8926 0.035 Uiso 1 1 calc R U . . .
H2A2 H 0.2522 0.7061 0.7910 0.035 Uiso 1 1 calc R U . . .
N3A N 0.19982(13) 0.52977(19) 0.82395(12) 0.0245(4) Uani 1 1 d . . . . .
C4A C 0.12044(16) 0.5542(2) 0.78927(14) 0.0257(5) Uani 1 1 d . . . . .
H4A H 0.1073 0.6416 0.7666 0.031 Uiso 1 1 calc R U . . .
C5A C 0.04973(15) 0.4583(2) 0.78226(15) 0.0251(5) Uani 1 1 d . . . . .
C6A C 0.05996(16) 0.3261(2) 0.81644(14) 0.0250(5) Uani 1 1 d . . . . .
O6A O 0.13611(10) 0.27281(16) 0.85056(10) 0.0260(4) Uani 1 1 d . . . . .
C7A C -0.01656(16) 0.2483(3) 0.81207(15) 0.0292(6) Uani 1 1 d . . . . .
H7A H -0.0121 0.1599 0.8350 0.035 Uiso 1 1 calc R U . . .
C8A C -0.09775(16) 0.2962(3) 0.77559(15) 0.0310(6) Uani 1 1 d . . . . .
H8A H -0.1476 0.2401 0.7746 0.037 Uiso 1 1 calc R U . . .
C9A C -0.10895(16) 0.4251(3) 0.74001(15) 0.0294(6) Uani 1 1 d . . . . .
C91A C -0.19887(17) 0.4786(3) 0.70312(18) 0.0408(7) Uani 1 1 d . . . . .
H91A H -0.2324 0.4940 0.7496 0.061 Uiso 1 1 calc R U . . .
H91B H -0.2296 0.4130 0.6627 0.061 Uiso 1 1 calc R U . . .
H91C H -0.1928 0.5635 0.6732 0.061 Uiso 1 1 calc R U . . .
C10A C -0.03443(16) 0.5031(3) 0.74363(15) 0.0287(6) Uani 1 1 d . . . . .
H10A H -0.0400 0.5905 0.7191 0.034 Uiso 1 1 calc R U . . .
C11A C 0.43069(16) 0.6563(2) 0.87867(17) 0.0289(6) Uani 1 1 d . . . . .
H11A H 0.4413 0.7358 0.8441 0.035 Uiso 1 1 calc R U . . .
H11B H 0.4181 0.6877 0.9348 0.035 Uiso 1 1 calc R U . . .
N12A N 0.50804(13) 0.5679(2) 0.89105(12) 0.0236(4) Uani 1 1 d . . . . .
C13A C 0.58557(16) 0.6170(2) 0.90394(15) 0.0252(5) Uani 1 1 d . . . . .
H13A H 0.5909 0.7121 0.9038 0.030 Uiso 1 1 calc R U . . .
C14A C 0.66521(16) 0.5401(2) 0.91854(14) 0.0241(5) Uani 1 1 d . . . . .
C15A C 0.66603(16) 0.3967(2) 0.92082(14) 0.0234(5) Uani 1 1 d . . . . .
O15A O 0.59594(10) 0.31994(16) 0.91170(10) 0.0257(4) Uani 1 1 d . . . . .
C16A C 0.74906(16) 0.3349(3) 0.93619(16) 0.0291(6) Uani 1 1 d . . . . .
H16A H 0.7521 0.2395 0.9378 0.035 Uiso 1 1 calc R U . . .
C17A C 0.82574(16) 0.4072(3) 0.94896(15) 0.0282(6) Uani 1 1 d . . . . .
H17A H 0.8801 0.3606 0.9595 0.034 Uiso 1 1 calc R U . . .
C18A C 0.82578(16) 0.5490(3) 0.94678(15) 0.0267(5) Uani 1 1 d . . . . .
C181 C 0.91061(17) 0.6262(3) 0.95941(17) 0.0334(6) Uani 1 1 d . . . . .
H18A H 0.9420 0.6075 0.9117 0.050 Uiso 1 1 calc R U . . .
H18B H 0.9468 0.5986 1.0134 0.050 Uiso 1 1 calc R U . . .
H18C H 0.8983 0.7226 0.9613 0.050 Uiso 1 1 calc R U . . .
C19A C 0.74554(16) 0.6109(2) 0.93145(15) 0.0257(5) Uani 1 1 d . . . . .
H19A H 0.7438 0.7063 0.9294 0.031 Uiso 1 1 calc R U . . .
C1B C 0.37166(16) 0.1365(2) 0.92237(15) 0.0244(5) Uani 1 1 d . . . . .
O1B O 0.29573(11) 0.18674(16) 0.90752(11) 0.0309(4) Uani 1 1 d . . . . .
O2B O 0.44247(10) 0.19435(16) 0.91590(11) 0.0292(4) Uani 1 1 d . . . . .
C2B C 0.37771(18) -0.0075(2) 0.9515(2) 0.0404(7) Uani 1 1 d . . . . .
H2B3 H 0.4279 -0.0506 0.9320 0.061 Uiso 1 1 calc R U . . .
H2B2 H 0.3238 -0.0550 0.9271 0.061 Uiso 1 1 calc R U . . .
H2B1 H 0.3854 -0.0109 1.0142 0.061 Uiso 1 1 calc R U . . .
C1C C 0.3745(2) 0.4801(3) 0.52892(18) 0.0460(8) Uani 1 1 d . . . . .
H1C3 H 0.3186 0.5025 0.4929 0.069 Uiso 1 1 calc R U . . .
H1C2 H 0.3895 0.3863 0.5191 0.069 Uiso 1 1 calc R U . . .
H1C1 H 0.4206 0.5392 0.5144 0.069 Uiso 1 1 calc R U . . .
O1C O 0.36727(13) 0.49763(19) 0.61529(11) 0.0391(5) Uani 1 1 d . . . . .
H1C H 0.3629 0.5799 0.6256 0.059 Uiso 1 1 calc R U . . .
C1D C 0.56366(17) 0.3782(3) 0.71179(17) 0.0332(6) Uani 1 1 d . . . . .
H1D3 H 0.5584 0.3865 0.6494 0.050 Uiso 1 1 calc R U . . .
H1D2 H 0.6030 0.3034 0.7319 0.050 Uiso 1 1 calc R U . . .
H1D1 H 0.5875 0.4617 0.7390 0.050 Uiso 1 1 calc R U . . .
O1D O 0.47899(11) 0.35309(17) 0.73377(11) 0.0297(4) Uani 1 1 d . . . . .
H1D H 0.4412 0.3984 0.7016 0.045 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1A 1.9014(15) . ?
Cu1 O6A 1.9078(16) . ?
Cu1 N3A 1.9283(19) . ?
Cu1 O1B 1.9379(16) . ?
Cu2 O15A 1.9048(16) . ?
Cu2 O1A 1.9248(15) . ?
Cu2 N12A 1.950(2) . ?
Cu2 O2B 1.9649(16) . ?
C1A O1A 1.437(3) . ?
C1A C2A 1.509(3) . ?
C1A C11A 1.509(3) . ?
C1A H1A 1.0000 . ?
C2A N3A 1.473(3) . ?
C2A H2A1 0.9900 . ?
C2A H2A2 0.9900 . ?
N3A C4A 1.283(3) . ?
C4A C5A 1.441(3) . ?
C4A H4A 0.9500 . ?
C5A C10A 1.416(3) . ?
C5A C6A 1.421(3) . ?
C6A O6A 1.323(3) . ?
C6A C7A 1.406(3) . ?
C7A C8A 1.378(3) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.400(4) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.383(4) . ?
C9A C91A 1.514(3) . ?
C91A H91A 0.9800 . ?
C91A H91B 0.9800 . ?
C91A H91C 0.9800 . ?
C10A H10A 0.9500 . ?
C11A N12A 1.472(3) . ?
C11A H11A 0.9900 . ?
C11A H11B 0.9900 . ?
N12A C13A 1.280(3) . ?
C13A C14A 1.436(3) . ?
C13A H13A 0.9500 . ?
C14A C19A 1.414(3) . ?
C14A C15A 1.427(3) . ?
C15A O15A 1.315(3) . ?
C15A C16A 1.409(3) . ?
C16A C17A 1.373(3) . ?
C16A H16A 0.9500 . ?
C17A C18A 1.411(4) . ?
C17A H17A 0.9500 . ?
C18A C19A 1.371(3) . ?
C18A C181 1.505(3) . ?
C181 H18A 0.9800 . ?
C181 H18B 0.9800 . ?
C181 H18C 0.9800 . ?
C19A H19A 0.9500 . ?
C1B O2B 1.257(3) . ?
C1B O1B 1.262(3) . ?
C1B C2B 1.502(3) . ?
C2B H2B3 0.9800 . ?
C2B H2B2 0.9800 . ?
C2B H2B1 0.9800 . ?
C1C O1C 1.400(3) . ?
C1C H1C3 0.9800 . ?
C1C H1C2 0.9800 . ?
C1C H1C1 0.9800 . ?
O1C H1C 0.8400 . ?
C1D O1D 1.432(3) . ?
C1D H1D3 0.9800 . ?
C1D H1D2 0.9800 . ?
C1D H1D1 0.9800 . ?
O1D H1D 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1A Cu1 O6A 174.67(7) . . ?
O1A Cu1 N3A 84.99(7) . . ?
O6A Cu1 N3A 93.62(8) . . ?
O1A Cu1 O1B 95.13(7) . . ?
O6A Cu1 O1B 86.22(7) . . ?
N3A Cu1 O1B 179.54(8) . . ?
O15A Cu2 O1A 177.42(7) . . ?
O15A Cu2 N12A 93.59(8) . . ?
O1A Cu2 N12A 84.07(7) . . ?
O15A Cu2 O2B 88.23(7) . . ?
O1A Cu2 O2B 93.82(7) . . ?
N12A Cu2 O2B 166.94(8) . . ?
O1A C1A C2A 109.30(19) . . ?
O1A C1A C11A 107.98(19) . . ?
C2A C1A C11A 114.0(2) . . ?
O1A C1A H1A 108.5 . . ?
C2A C1A H1A 108.5 . . ?
C11A C1A H1A 108.5 . . ?
C1A O1A Cu1 114.54(13) . . ?
C1A O1A Cu2 110.64(13) . . ?
Cu1 O1A Cu2 133.01(9) . . ?
N3A C2A C1A 108.41(19) . . ?
N3A C2A H2A1 110.0 . . ?
C1A C2A H2A1 110.0 . . ?
N3A C2A H2A2 110.0 . . ?
C1A C2A H2A2 110.0 . . ?
H2A1 C2A H2A2 108.4 . . ?
C4A N3A C2A 121.1(2) . . ?
C4A N3A Cu1 126.93(17) . . ?
C2A N3A Cu1 111.99(15) . . ?
N3A C4A C5A 124.7(2) . . ?
N3A C4A H4A 117.7 . . ?
C5A C4A H4A 117.7 . . ?
C10A C5A C6A 119.5(2) . . ?
C10A C5A C4A 117.2(2) . . ?
C6A C5A C4A 123.2(2) . . ?
O6A C6A C7A 119.0(2) . . ?
O6A C6A C5A 124.2(2) . . ?
C7A C6A C5A 116.8(2) . . ?
C6A O6A Cu1 126.79(15) . . ?
C8A C7A C6A 122.2(2) . . ?
C8A C7A H7A 118.9 . . ?
C6A C7A H7A 118.9 . . ?
C7A C8A C9A 121.9(2) . . ?
C7A C8A H8A 119.0 . . ?
C9A C8A H8A 119.0 . . ?
C10A C9A C8A 116.8(2) . . ?
C10A C9A C91A 121.7(2) . . ?
C8A C9A C91A 121.5(2) . . ?
C9A C91A H91A 109.5 . . ?
C9A C91A H91B 109.5 . . ?
H91A C91A H91B 109.5 . . ?
C9A C91A H91C 109.5 . . ?
H91A C91A H91C 109.5 . . ?
H91B C91A H91C 109.5 . . ?
C9A C10A C5A 122.8(2) . . ?
C9A C10A H10A 118.6 . . ?
C5A C10A H10A 118.6 . . ?
N12A C11A C1A 107.4(2) . . ?
N12A C11A H11A 110.2 . . ?
C1A C11A H11A 110.2 . . ?
N12A C11A H11B 110.2 . . ?
C1A C11A H11B 110.2 . . ?
H11A C11A H11B 108.5 . . ?
C13A N12A C11A 120.9(2) . . ?
C13A N12A Cu2 126.46(17) . . ?
C11A N12A Cu2 112.63(15) . . ?
N12A C13A C14A 125.4(2) . . ?
N12A C13A H13A 117.3 . . ?
C14A C13A H13A 117.3 . . ?
C19A C14A C15A 119.4(2) . . ?
C19A C14A C13A 117.9(2) . . ?
C15A C14A C13A 122.7(2) . . ?
O15A C15A C16A 118.5(2) . . ?
O15A C15A C14A 125.1(2) . . ?
C16A C15A C14A 116.4(2) . . ?
C15A O15A Cu2 126.79(15) . . ?
C17A C16A C15A 122.5(2) . . ?
C17A C16A H16A 118.7 . . ?
C15A C16A H16A 118.7 . . ?
C16A C17A C18A 121.6(2) . . ?
C16A C17A H17A 119.2 . . ?
C18A C17A H17A 119.2 . . ?
C19A C18A C17A 116.7(2) . . ?
C19A C18A C181 122.6(2) . . ?
C17A C18A C181 120.7(2) . . ?
C18A C181 H18A 109.5 . . ?
C18A C181 H18B 109.5 . . ?
H18A C181 H18B 109.5 . . ?
C18A C181 H18C 109.5 . . ?
H18A C181 H18C 109.5 . . ?
H18B C181 H18C 109.5 . . ?
C18A C19A C14A 123.4(2) . . ?
C18A C19A H19A 118.3 . . ?
C14A C19A H19A 118.3 . . ?
O2B C1B O1B 126.9(2) . . ?
O2B C1B C2B 116.8(2) . . ?
O1B C1B C2B 116.3(2) . . ?
C1B O1B Cu1 134.87(15) . . ?
C1B O2B Cu2 135.54(15) . . ?
C1B C2B H2B3 109.5 . . ?
C1B C2B H2B2 109.5 . . ?
H2B3 C2B H2B2 109.5 . . ?
C1B C2B H2B1 109.5 . . ?
H2B3 C2B H2B1 109.5 . . ?
H2B2 C2B H2B1 109.5 . . ?
O1C C1C H1C3 109.5 . . ?
O1C C1C H1C2 109.5 . . ?
H1C3 C1C H1C2 109.5 . . ?
O1C C1C H1C1 109.5 . . ?
H1C3 C1C H1C1 109.5 . . ?
H1C2 C1C H1C1 109.5 . . ?
C1C O1C H1C 109.5 . . ?
O1D C1D H1D3 109.5 . . ?
O1D C1D H1D2 109.5 . . ?
H1D3 C1D H1D2 109.5 . . ?
O1D C1D H1D1 109.5 . . ?
H1D3 C1D H1D1 109.5 . . ?
H1D2 C1D H1D1 109.5 . . ?
C1D O1D H1D 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2A C1A O1A Cu1 25.9(2) . . . . ?
C11A C1A O1A Cu1 150.38(15) . . . . ?
C2A C1A O1A Cu2 -167.38(15) . . . . ?
C11A C1A O1A Cu2 -42.9(2) . . . . ?
O1A C1A C2A N3A -35.3(3) . . . . ?
C11A C1A C2A N3A -156.2(2) . . . . ?
C1A C2A N3A C4A -150.5(2) . . . . ?
C1A C2A N3A Cu1 30.0(2) . . . . ?
C2A N3A C4A C5A -173.6(2) . . . . ?
Cu1 N3A C4A C5A 5.8(3) . . . . ?
N3A C4A C5A C10A 178.7(2) . . . . ?
N3A C4A C5A C6A 2.5(4) . . . . ?
C10A C5A C6A O6A 177.1(2) . . . . ?
C4A C5A C6A O6A -6.8(4) . . . . ?
C10A C5A C6A C7A -2.1(3) . . . . ?
C4A C5A C6A C7A 174.0(2) . . . . ?
C7A C6A O6A Cu1 -178.37(15) . . . . ?
C5A C6A O6A Cu1 2.4(3) . . . . ?
O6A C6A C7A C8A -178.5(2) . . . . ?
C5A C6A C7A C8A 0.8(3) . . . . ?
C6A C7A C8A C9A 0.5(4) . . . . ?
C7A C8A C9A C10A -0.4(4) . . . . ?
C7A C8A C9A C91A -177.7(2) . . . . ?
C8A C9A C10A C5A -1.0(4) . . . . ?
C91A C9A C10A C5A 176.2(2) . . . . ?
C6A C5A C10A C9A 2.3(4) . . . . ?
C4A C5A C10A C9A -174.0(2) . . . . ?
O1A C1A C11A N12A 42.4(2) . . . . ?
C2A C1A C11A N12A 164.0(2) . . . . ?
C1A C11A N12A C13A 158.6(2) . . . . ?
C1A C11A N12A Cu2 -23.7(2) . . . . ?
C11A N12A C13A C14A 178.6(2) . . . . ?
Cu2 N12A C13A C14A 1.3(3) . . . . ?
N12A C13A C14A C19A 179.8(2) . . . . ?
N12A C13A C14A C15A -0.5(4) . . . . ?
C19A C14A C15A O15A 178.4(2) . . . . ?
C13A C14A C15A O15A -1.3(4) . . . . ?
C19A C14A C15A C16A 0.0(3) . . . . ?
C13A C14A C15A C16A -179.7(2) . . . . ?
C16A C15A O15A Cu2 -179.60(15) . . . . ?
C14A C15A O15A Cu2 2.0(3) . . . . ?
O15A C15A C16A C17A -178.1(2) . . . . ?
C14A C15A C16A C17A 0.4(3) . . . . ?
C15A C16A C17A C18A -0.5(4) . . . . ?
C16A C17A C18A C19A 0.1(4) . . . . ?
C16A C17A C18A C181 -178.9(2) . . . . ?
C17A C18A C19A C14A 0.3(3) . . . . ?
C181 C18A C19A C14A 179.3(2) . . . . ?
C15A C14A C19A C18A -0.4(3) . . . . ?
C13A C14A C19A C18A 179.4(2) . . . . ?
O2B C1B O1B Cu1 3.0(4) . . . . ?
C2B C1B O1B Cu1 -177.46(19) . . . . ?
O1B C1B O2B Cu2 4.6(4) . . . . ?
C2B C1B O2B Cu2 -174.94(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C4A H4A O1D 0.95 2.49 3.341(3) 148.8 2_556
C11A H11B O15A 0.99 2.48 3.417(3) 158.7 3_667
O1C H1C O6A 0.84 1.96 2.793(2) 174.9 2_556
O1D H1D O1C 0.84 1.91 2.738(3) 170.8 .

_refine_diff_density_max         0.386
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.061

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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 1569986'
_audit_update_record             
;
2017-08-21 deposited with the CCDC.
2018-08-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H20 Cu N2 O3, C H4 O'
_chemical_formula_sum            'C20 H24 Cu N2 O4'
_chemical_formula_weight         419.95

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

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

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

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

_cell_length_a                   11.98914(13)
_cell_length_b                   10.38861(9)
_cell_length_c                   16.00151(14)
_cell_angle_alpha                90
_cell_angle_beta                 110.5792(11)
_cell_angle_gamma                90
_cell_volume                     1865.82(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    130(1)
_cell_measurement_reflns_used    13463
_cell_measurement_theta_min      2.9310
_cell_measurement_theta_max      75.4220

_exptl_crystal_description       prism
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_F_000             876
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    1.896
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.43010
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      130(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.5357
_diffrn_measurement_method       '/w scan'
_diffrn_reflns_number            17812
_diffrn_reflns_av_unetI/netI     0.0112
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         5.181
_diffrn_reflns_theta_max         75.614
_diffrn_reflns_theta_full        67.500
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3816
_reflns_number_gt                3728
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.38.34a (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.34a (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.34a (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury (MacRae et al., 2009)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0577P)²+2.9264P] 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         3816
_refine_ls_number_parameters     266
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1186
_refine_ls_wR_factor_gt          0.1180
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.078
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.49909(3) 0.24866(3) 0.49549(2) 0.01811(13) Uani 1 1 d . . . . .
C1 C 0.5008(2) 0.2459(2) 0.71102(15) 0.0226(5) Uani 1 1 d . . . . .
H1A2 H 0.5686 0.2641 0.7656 0.027 Uiso 0.579(5) 1 d R U P A 1
O1 O 0.3999(3) 0.2105(3) 0.73428(18) 0.0249(8) Uani 0.579(5) 1 d . . P A 1
H1B H 0.4020 0.2506 0.7804 0.037 Uiso 0.579(5) 1 calc R U P A 1
H1A1 H 0.4329 0.2268 0.7296 0.030 Uiso 0.421(5) 1 d R U P A 2
O1' O 0.6001(4) 0.2838(4) 0.7868(2) 0.0261(11) Uani 0.421(5) 1 d . . P A 2
H1O H 0.5904 0.2578 0.8335 0.039 Uiso 0.421(5) 1 calc R U P A 2
C2 C 0.5293(2) 0.1288(2) 0.66443(14) 0.0223(4) Uani 1 1 d . . . . .
H2B H 0.6145 0.1314 0.6709 0.027 Uiso 1 1 calc R U . . .
H2A H 0.5160 0.0496 0.6941 0.027 Uiso 1 1 calc R U . . .
N3 N 0.45624(16) 0.12321(18) 0.56910(11) 0.0192(4) Uani 1 1 d . . . . .
C4 C 0.3804(2) 0.0319(2) 0.53977(14) 0.0204(4) Uani 1 1 d . . . . .
H4 H 0.3741 -0.0297 0.5818 0.024 Uiso 1 1 calc R U . . .
C5 C 0.3039(2) 0.0156(2) 0.44787(15) 0.0203(4) Uani 1 1 d . . . . .
C6 C 0.31014(19) 0.0933(2) 0.37686(14) 0.0198(4) Uani 1 1 d . . . . .
O6 O 0.39279(14) 0.18122(15) 0.38533(10) 0.0213(3) Uani 1 1 d . . . . .
C7 C 0.2235(2) 0.0707(2) 0.29152(15) 0.0243(5) Uani 1 1 d . . . . .
H7 H 0.2213 0.1251 0.2432 0.029 Uiso 1 1 calc R U . . .
C8 C 0.1423(2) -0.0281(3) 0.27680(16) 0.0283(5) Uani 1 1 d . . . . .
H8 H 0.0857 -0.0402 0.2185 0.034 Uiso 1 1 calc R U . . .
C9 C 0.1406(2) -0.1118(2) 0.34558(17) 0.0286(5) Uani 1 1 d . . . . .
C91 C 0.0568(3) -0.2256(3) 0.3277(2) 0.0433(7) Uani 1 1 d . . . . .
H91C H 0.0792 -0.2888 0.2910 0.065 Uiso 1 1 calc R U . . .
H91B H -0.0250 -0.1964 0.2961 0.065 Uiso 1 1 calc R U . . .
H91A H 0.0618 -0.2652 0.3845 0.065 Uiso 1 1 calc R U . . .
C10 C 0.2205(2) -0.0864(2) 0.43002(16) 0.0248(5) Uani 1 1 d . . . . .
H10 H 0.2195 -0.1394 0.4781 0.030 Uiso 1 1 calc R U . . .
C11 C 0.4738(2) 0.3655(2) 0.65102(15) 0.0228(5) Uani 1 1 d . . . . .
H11B H 0.3882 0.3654 0.6133 0.027 Uiso 1 1 calc R U . . .
H11A H 0.4892 0.4435 0.6890 0.027 Uiso 1 1 calc R U . . .
N12 N 0.54534(16) 0.37178(18) 0.59316(12) 0.0195(4) Uani 1 1 d . . . . .
C13 C 0.6206(2) 0.4633(2) 0.60318(14) 0.0206(4) Uani 1 1 d . . . . .
H13 H 0.6286 0.5236 0.6495 0.025 Uiso 1 1 calc R U . . .
C14 C 0.6943(2) 0.4819(2) 0.54962(15) 0.0203(4) Uani 1 1 d . . . . .
C15 C 0.68404(19) 0.4068(2) 0.47306(14) 0.0200(4) Uani 1 1 d . . . . .
O15 O 0.60213(14) 0.31795(16) 0.43936(10) 0.0223(3) Uani 1 1 d . . . . .
C16 C 0.7653(2) 0.4340(2) 0.42947(15) 0.0238(5) Uani 1 1 d . . . . .
H16 H 0.7647 0.3820 0.3804 0.029 Uiso 1 1 calc R U . . .
C17 C 0.8456(2) 0.5340(2) 0.45617(16) 0.0254(5) Uani 1 1 d . . . . .
H17 H 0.8982 0.5494 0.4246 0.030 Uiso 1 1 calc R U . . .
C18 C 0.8520(2) 0.6139(2) 0.52863(16) 0.0249(5) Uani 1 1 d . . . . .
C181 C 0.9354(2) 0.7278(3) 0.55364(19) 0.0324(6) Uani 1 1 d . . . . .
H18A H 0.9807 0.7324 0.5134 0.049 Uiso 1 1 calc R U . . .
H18B H 0.8890 0.8070 0.5486 0.049 Uiso 1 1 calc R U . . .
H18C H 0.9904 0.7179 0.6152 0.049 Uiso 1 1 calc R U . . .
C19 C 0.7771(2) 0.5844(2) 0.57461(15) 0.0225(4) Uani 1 1 d . . . . .
H19 H 0.7814 0.6350 0.6251 0.027 Uiso 1 1 calc R U . . .
C1A C 0.1532(4) 0.5225(5) 0.1553(4) 0.0778(13) Uani 1 1 d . . . . .
H1A3 H 0.1205 0.5231 0.2035 0.117 Uiso 0.667 1 d R U P B 1
H1A4 H 0.1170 0.4522 0.1138 0.117 Uiso 0.667 1 d R U P B 1
H1A5 H 0.1357 0.6048 0.1233 0.117 Uiso 0.667 1 d R U P B 1
H1A6 H 0.1176 0.5141 0.2016 0.117 Uiso 0.33 1 d R U P C 2
H1A7 H 0.0937 0.5565 0.1006 0.117 Uiso 0.33 1 d R U P C 2
H1A8 H 0.2212 0.5815 0.1759 0.117 Uiso 0.33 1 d R U P C 2
O1A O 0.2664(6) 0.5048(7) 0.1887(4) 0.108(2) Uani 0.667 1 d . U P D 1
H1A H 0.2821 0.4289 0.1785 0.130 Uiso 0.667 1 d R U P D 1
O1A' O 0.1902(8) 0.3970(10) 0.1383(8) 0.089(3) Uani 0.333 1 d . U P D 2
H1A' H 0.1299 0.3513 0.1128 0.107 Uiso 0.333 1 d R U P D 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O15 1.9055(15) . ?
Cu1 O6 1.9086(15) . ?
Cu1 N3 1.9431(18) . ?
Cu1 N12 1.9434(18) . ?
C1 O1' 1.424(4) . ?
C1 O1 1.433(3) . ?
C1 C2 1.528(3) . ?
C1 C11 1.533(3) . ?
C1 H1A2 0.9800 . ?
C1 H1A1 0.9799 . ?
O1 H1B 0.8400 . ?
O1' H1O 0.8400 . ?
C2 N3 1.469(3) . ?
C2 H2B 0.9900 . ?
C2 H2A 0.9900 . ?
N3 C4 1.284(3) . ?
C4 C5 1.444(3) . ?
C4 H4 0.9500 . ?
C5 C10 1.415(3) . ?
C5 C6 1.417(3) . ?
C6 O6 1.319(3) . ?
C6 C7 1.415(3) . ?
C7 C8 1.377(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.409(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.380(3) . ?
C9 C91 1.512(4) . ?
C91 H91C 0.9800 . ?
C91 H91B 0.9800 . ?
C91 H91A 0.9800 . ?
C10 H10 0.9500 . ?
C11 N12 1.469(3) . ?
C11 H11B 0.9900 . ?
C11 H11A 0.9900 . ?
N12 C13 1.282(3) . ?
C13 C14 1.444(3) . ?
C13 H13 0.9500 . ?
C14 C19 1.415(3) . ?
C14 C15 1.421(3) . ?
C15 O15 1.317(3) . ?
C15 C16 1.412(3) . ?
C16 C17 1.378(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.406(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.380(3) . ?
C18 C181 1.509(3) . ?
C181 H18A 0.9800 . ?
C181 H18B 0.9800 . ?
C181 H18C 0.9800 . ?
C19 H19 0.9500 . ?
C1A O1A 1.285(7) . ?
C1A O1A' 1.434(10) . ?
C1A H1A3 0.9800 . ?
C1A H1A4 0.9800 . ?
C1A H1A5 0.9800 . ?
C1A H1A6 0.9800 . ?
C1A H1A7 0.9800 . ?
C1A H1A8 0.9800 . ?
O1A H1A 0.8400 . ?
O1A' H1A' 0.8400 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O15 Cu1 O6 92.09(7) . . ?
O15 Cu1 N3 153.18(8) . . ?
O6 Cu1 N3 94.63(7) . . ?
O15 Cu1 N12 94.67(7) . . ?
O6 Cu1 N12 153.31(8) . . ?
N3 Cu1 N12 90.88(8) . . ?
O1' C1 C2 111.8(3) . . ?
O1 C1 C2 106.0(2) . . ?
O1' C1 C11 103.8(2) . . ?
O1 C1 C11 111.0(2) . . ?
C2 C1 C11 111.98(18) . . ?
O1 C1 H1A2 109.2 . . ?
C2 C1 H1A2 109.3 . . ?
C11 C1 H1A2 109.2 . . ?
O1' C1 H1A1 109.4 . . ?
C2 C1 H1A1 109.8 . . ?
C11 C1 H1A1 109.8 . . ?
C1 O1 H1B 109.5 . . ?
C1 O1' H1O 109.5 . . ?
N3 C2 C1 112.59(18) . . ?
N3 C2 H2B 109.1 . . ?
C1 C2 H2B 109.1 . . ?
N3 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
H2B C2 H2A 107.8 . . ?
C4 N3 C2 119.74(19) . . ?
C4 N3 Cu1 125.35(15) . . ?
C2 N3 Cu1 114.51(14) . . ?
N3 C4 C5 125.0(2) . . ?
N3 C4 H4 117.5 . . ?
C5 C4 H4 117.5 . . ?
C10 C5 C6 119.8(2) . . ?
C10 C5 C4 116.4(2) . . ?
C6 C5 C4 123.8(2) . . ?
O6 C6 C7 118.95(19) . . ?
O6 C6 C5 124.2(2) . . ?
C7 C6 C5 116.9(2) . . ?
C6 O6 Cu1 125.64(13) . . ?
C8 C7 C6 121.6(2) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C7 C8 C9 122.0(2) . . ?
C7 C8 H8 119.0 . . ?
C9 C8 H8 119.0 . . ?
C10 C9 C8 116.8(2) . . ?
C10 C9 C91 121.4(2) . . ?
C8 C9 C91 121.8(2) . . ?
C9 C91 H91C 109.5 . . ?
C9 C91 H91B 109.5 . . ?
H91C C91 H91B 109.5 . . ?
C9 C91 H91A 109.5 . . ?
H91C C91 H91A 109.5 . . ?
H91B C91 H91A 109.5 . . ?
C9 C10 C5 122.6(2) . . ?
C9 C10 H10 118.7 . . ?
C5 C10 H10 118.7 . . ?
N12 C11 C1 112.88(18) . . ?
N12 C11 H11B 109.0 . . ?
C1 C11 H11B 109.0 . . ?
N12 C11 H11A 109.0 . . ?
C1 C11 H11A 109.0 . . ?
H11B C11 H11A 107.8 . . ?
C13 N12 C11 119.73(18) . . ?
C13 N12 Cu1 125.32(15) . . ?
C11 N12 Cu1 114.41(14) . . ?
N12 C13 C14 125.2(2) . . ?
N12 C13 H13 117.4 . . ?
C14 C13 H13 117.4 . . ?
C19 C14 C15 119.8(2) . . ?
C19 C14 C13 116.6(2) . . ?
C15 C14 C13 123.5(2) . . ?
O15 C15 C16 118.9(2) . . ?
O15 C15 C14 124.3(2) . . ?
C16 C15 C14 116.7(2) . . ?
C15 O15 Cu1 125.83(14) . . ?
C17 C16 C15 121.7(2) . . ?
C17 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
C16 C17 C18 122.1(2) . . ?
C16 C17 H17 119.0 . . ?
C18 C17 H17 119.0 . . ?
C19 C18 C17 116.8(2) . . ?
C19 C18 C181 121.8(2) . . ?
C17 C18 C181 121.4(2) . . ?
C18 C181 H18A 109.5 . . ?
C18 C181 H18B 109.5 . . ?
H18A C181 H18B 109.5 . . ?
C18 C181 H18C 109.5 . . ?
H18A C181 H18C 109.5 . . ?
H18B C181 H18C 109.5 . . ?
C18 C19 C14 122.7(2) . . ?
C18 C19 H19 118.7 . . ?
C14 C19 H19 118.7 . . ?
O1A C1A H1A3 109.2 . . ?
O1A C1A H1A4 109.1 . . ?
H1A3 C1A H1A4 109.5 . . ?
O1A C1A H1A5 110.1 . . ?
H1A3 C1A H1A5 109.5 . . ?
H1A4 C1A H1A5 109.5 . . ?
O1A' C1A H1A6 108.0 . . ?
O1A' C1A H1A7 109.5 . . ?
H1A6 C1A H1A7 109.5 . . ?
O1A' C1A H1A8 110.9 . . ?
H1A6 C1A H1A8 109.5 . . ?
H1A7 C1A H1A8 109.5 . . ?
C1A O1A H1A 109.3 . . ?
C1A O1A' H1A' 109.6 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1' C1 C2 N3 -153.5(2) . . . . ?
O1 C1 C2 N3 83.8(2) . . . . ?
C11 C1 C2 N3 -37.5(3) . . . . ?
C1 C2 N3 C4 -113.9(2) . . . . ?
C1 C2 N3 Cu1 73.0(2) . . . . ?
C2 N3 C4 C5 -179.8(2) . . . . ?
Cu1 N3 C4 C5 -7.5(3) . . . . ?
N3 C4 C5 C10 -175.8(2) . . . . ?
N3 C4 C5 C6 5.4(4) . . . . ?
C10 C5 C6 O6 -172.5(2) . . . . ?
C4 C5 C6 O6 6.2(3) . . . . ?
C10 C5 C6 C7 5.5(3) . . . . ?
C4 C5 C6 C7 -175.8(2) . . . . ?
C7 C6 O6 Cu1 167.97(15) . . . . ?
C5 C6 O6 Cu1 -14.0(3) . . . . ?
O6 C6 C7 C8 173.6(2) . . . . ?
C5 C6 C7 C8 -4.6(3) . . . . ?
C6 C7 C8 C9 0.2(4) . . . . ?
C7 C8 C9 C10 3.2(4) . . . . ?
C7 C8 C9 C91 -175.8(3) . . . . ?
C8 C9 C10 C5 -2.2(4) . . . . ?
C91 C9 C10 C5 176.8(2) . . . . ?
C6 C5 C10 C9 -2.3(3) . . . . ?
C4 C5 C10 C9 178.9(2) . . . . ?
O1' C1 C11 N12 85.7(3) . . . . ?
O1 C1 C11 N12 -153.4(2) . . . . ?
C2 C1 C11 N12 -35.1(3) . . . . ?
C1 C11 N12 C13 -115.6(2) . . . . ?
C1 C11 N12 Cu1 72.5(2) . . . . ?
C11 N12 C13 C14 -178.6(2) . . . . ?
Cu1 N12 C13 C14 -7.6(3) . . . . ?
N12 C13 C14 C19 -176.3(2) . . . . ?
N12 C13 C14 C15 6.1(4) . . . . ?
C19 C14 C15 O15 -173.0(2) . . . . ?
C13 C14 C15 O15 4.4(3) . . . . ?
C19 C14 C15 C16 4.6(3) . . . . ?
C13 C14 C15 C16 -178.0(2) . . . . ?
C16 C15 O15 Cu1 170.46(15) . . . . ?
C14 C15 O15 Cu1 -11.9(3) . . . . ?
O15 C15 C16 C17 173.6(2) . . . . ?
C14 C15 C16 C17 -4.1(3) . . . . ?
C15 C16 C17 C18 0.6(4) . . . . ?
C16 C17 C18 C19 2.6(3) . . . . ?
C16 C17 C18 C181 -176.3(2) . . . . ?
C17 C18 C19 C14 -2.0(3) . . . . ?
C181 C18 C19 C14 176.9(2) . . . . ?
C15 C14 C19 C18 -1.6(3) . . . . ?
C13 C14 C19 C18 -179.2(2) . . . . ?

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
O1 H1B O6 0.84 1.86 2.694(3) 171.3 4_566
O1' H1O O15 0.84 1.83 2.652(4) 166.6 4_566
C4 H4 O1A 0.95 2.49 3.160(6) 127.2 4_566
C13 H13 O1A 0.95 2.47 3.140(6) 127.9 3_666
C1A H1A8 O1' 0.98 2.45 3.425(6) 172.7 3_666
O1A H1A O1 0.84 2.00 2.697(7) 139.8 4_565

_refine_diff_density_max         0.600
_refine_diff_density_min         -0.540
_refine_diff_density_rms         0.073

