# 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 2022

####################################################################### 
# 
# 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_1a
_database_code_depnum_ccdc_archive 'CCDC 2076993'
loop_
_audit_author_name
_audit_author_address
'Barbara Modec'
;University of Ljubljana
Slovenia
;
_audit_update_record             
;
2021-04-12 deposited with the CCDC.	2022-03-18 downloaded from the CCDC.
;
_audit_creation_date             2021-03-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H26 Cu N4 O6'
_chemical_formula_sum            'C24 H26 Cu N4 O6'
_chemical_formula_weight         530.03
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_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                   9.8103(3)
_cell_length_b                   5.9728(2)
_cell_length_c                   19.2540(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.697(3)
_cell_angle_gamma                90
_cell_volume                     1115.22(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2358
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      74.4210
_cell_measurement_theta_min      4.8010
_shelx_estimated_absorpt_T_max   0.931
_shelx_estimated_absorpt_T_min   0.611
_exptl_absorpt_coefficient_mu    1.822
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42110
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             550
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            5193
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.773
_diffrn_reflns_theta_min         4.647
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector_area_resol_mean 10.4933
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -47.00   27.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5153   37.0000  -60.0000 74

#__ type_ start__ end____ width___ exp.time_
  2 omega  -48.00   -2.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5153   37.0000 -150.0000 46

#__ type_ start__ end____ width___ exp.time_
  3 omega   36.00   63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5153  -99.0000 -120.0000 27

#__ type_ start__ end____ width___ exp.time_
  4 omega -139.00 -113.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -30.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega  -84.00  -31.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -30.0000  150.0000 53

#__ type_ start__ end____ width___ exp.time_
  6 omega   30.00  107.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -94.0000 -150.0000 77

#__ type_ start__ end____ width___ exp.time_
  7 omega   50.00   75.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -30.0000   60.0000 25

#__ type_ start__ end____ width___ exp.time_
  8 omega   43.00   69.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -45.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  9 omega   39.00   99.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -45.0000  -30.0000 60

#__ type_ start__ end____ width___ exp.time_
 10 omega   86.00  163.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   45.0000   60.0000 77

#__ type_ start__ end____ width___ exp.time_
 11 omega   30.00   58.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -94.0000  -90.0000 28

#__ type_ start__ end____ width___ exp.time_
 12 omega   59.00   85.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -94.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega   93.00  131.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   45.0000   90.0000 38

#__ type_ start__ end____ width___ exp.time_
 14 omega  134.00  176.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   45.0000   90.0000 42

#__ type_ start__ end____ width___ exp.time_
 15 omega   76.00  101.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -94.0000  -60.0000 25

#__ type_ start__ end____ width___ exp.time_
 16 omega   32.00  102.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.5000 -111.0000 -180.0000 70

#__ type_ start__ end____ width___ exp.time_
 17 omega   25.00   64.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -94.0000  -60.0000 39

#__ type_ start__ end____ width___ exp.time_
 18 omega   59.00   84.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -30.0000   30.0000 25

#__ type_ start__ end____ width___ exp.time_
 19 omega  128.00  157.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  111.0000  -60.0000 29
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0796988000
_diffrn_orient_matrix_UB_12      -0.2161820000
_diffrn_orient_matrix_UB_13      0.0233252000
_diffrn_orient_matrix_UB_21      -0.1373620000
_diffrn_orient_matrix_UB_22      -0.1275841000
_diffrn_orient_matrix_UB_23      -0.0032909000
_diffrn_orient_matrix_UB_31      0.0048599000
_diffrn_orient_matrix_UB_32      -0.0594703000
_diffrn_orient_matrix_UB_33      -0.0774067000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1991
_reflns_number_total             2266
_reflns_odcompleteness_completeness 99.56
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     73.11
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.291
_refine_diff_density_min         -0.478
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       0.0041(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2266
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0308
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0481P)²+0.3029P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0805
_refine_ls_wR_factor_ref         0.0862
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.500000 0.500000 0.500000 0.01467(14) Uani 1 2 d S T P . .
O1 O 0.61695(12) 0.2286(2) 0.54258(6) 0.0184(3) Uani 1 1 d . . . . .
O2 O 0.82444(13) 0.8569(3) 0.68473(7) 0.0267(3) Uani 1 1 d . . . . .
H2 H 0.815(3) 0.928(5) 0.6465(16) 0.041(7) Uiso 1 1 d . . . . .
O11 O 0.81533(13) 0.0398(2) 0.55166(7) 0.0262(3) Uani 1 1 d . . . . .
N1 N 0.70001(14) 0.5055(2) 0.44653(7) 0.0158(3) Uani 1 1 d . . . . .
N2 N 0.59358(15) 0.7050(3) 0.57457(8) 0.0183(3) Uani 1 1 d . . . . .
H2A H 0.666(3) 0.742(5) 0.5607(13) 0.034(7) Uiso 1 1 d . . . . .
H2B H 0.544(3) 0.825(5) 0.5705(13) 0.037(7) Uiso 1 1 d . . . . .
C10 C 0.74159(17) 0.6493(3) 0.39858(8) 0.0172(3) Uani 1 1 d . . . . .
C11 C 0.65293(18) 0.8272(3) 0.37237(9) 0.0213(4) Uani 1 1 d . . . . .
H11 H 0.567042 0.841934 0.386745 0.026 Uiso 1 1 calc R . . . .
C12 C 0.6937(2) 0.9772(3) 0.32594(10) 0.0248(4) Uani 1 1 d . . . . .
H12 H 0.634883 1.093355 0.308814 0.030 Uiso 1 1 calc R . . . .
C13 C 0.8245(2) 0.9579(3) 0.30359(9) 0.0249(4) Uani 1 1 d . . . . .
H13 H 0.851525 1.062382 0.272562 0.030 Uiso 1 1 calc R . . . .
C14 C 0.91029(18) 0.7867(3) 0.32748(9) 0.0225(4) Uani 1 1 d . . . . .
H14 H 0.995891 0.775118 0.312586 0.027 Uiso 1 1 calc R . . . .
C15 C 0.87101(17) 0.6253(3) 0.37483(8) 0.0185(3) Uani 1 1 d . . . . .
C16 C 0.95392(17) 0.4407(3) 0.39973(9) 0.0221(4) Uani 1 1 d . . . . .
H16 H 1.037596 0.416497 0.383806 0.026 Uiso 1 1 calc R . . . .
C17 C 0.91079(17) 0.2976(3) 0.44736(9) 0.0204(4) Uani 1 1 d . . . . .
H17 H 0.964423 0.175304 0.464290 0.024 Uiso 1 1 calc R . . . .
C18 C 0.78315(16) 0.3393(3) 0.47034(8) 0.0164(3) Uani 1 1 d . . . . .
C19 C 0.73518(16) 0.1891(3) 0.52599(8) 0.0174(3) Uani 1 1 d . . . . .
C21 C 0.61705(19) 0.6336(3) 0.64891(9) 0.0222(4) Uani 1 1 d . . . . .
H21A H 0.672640 0.498545 0.653205 0.027 Uiso 1 1 calc R . . . .
H21B H 0.529044 0.597773 0.663343 0.027 Uiso 1 1 calc R . . . .
C22 C 0.68881(17) 0.8111(3) 0.69776(9) 0.0221(4) Uani 1 1 d . . . . .
H22A H 0.635070 0.948016 0.692161 0.026 Uiso 1 1 calc R . . . .
H22B H 0.692669 0.761455 0.745984 0.026 Uiso 1 1 calc R . . . .


_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 O1 2.0813(12) . ?
Cu1 O1 2.0813(12) 3_666 ?
Cu1 N1 2.3498(14) 3_666 ?
Cu1 N1 2.3498(14) . ?
Cu1 N2 2.0014(15) 3_666 ?
Cu1 N2 2.0014(15) . ?
O1 C19 1.271(2) . ?
O2 C22 1.417(2) . ?
O11 C19 1.241(2) . ?
N1 C10 1.368(2) . ?
N1 C18 1.322(2) . ?
N2 C21 1.478(2) . ?
C10 C11 1.417(2) . ?
C10 C15 1.420(2) . ?
C11 C12 1.367(3) . ?
C12 C13 1.419(3) . ?
C13 C14 1.360(3) . ?
C14 C15 1.419(2) . ?
C15 C16 1.410(3) . ?
C16 C17 1.367(3) . ?
C17 C18 1.412(2) . ?
C18 C19 1.525(2) . ?
C21 C22 1.518(2) . ?

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 Cu1 O1 180.0 . 3_666 ?
O1 Cu1 N1 74.72(5) . . ?
O1 Cu1 N1 105.28(5) 3_666 . ?
O1 Cu1 N1 105.28(5) . 3_666 ?
O1 Cu1 N1 74.72(5) 3_666 3_666 ?
N1 Cu1 N1 180.0 3_666 . ?
N2 Cu1 O1 91.62(5) . . ?
N2 Cu1 O1 91.62(5) 3_666 3_666 ?
N2 Cu1 O1 88.38(5) . 3_666 ?
N2 Cu1 O1 88.38(5) 3_666 . ?
N2 Cu1 N1 90.98(6) . 3_666 ?
N2 Cu1 N1 89.02(6) 3_666 3_666 ?
N2 Cu1 N1 90.98(6) 3_666 . ?
N2 Cu1 N1 89.02(6) . . ?
N2 Cu1 N2 180.00(6) 3_666 . ?
C19 O1 Cu1 121.01(11) . . ?
C10 N1 Cu1 131.20(11) . . ?
C18 N1 Cu1 110.47(11) . . ?
C18 N1 C10 118.31(14) . . ?
C21 N2 Cu1 120.36(12) . . ?
N1 C10 C11 118.79(15) . . ?
N1 C10 C15 121.76(16) . . ?
C11 C10 C15 119.45(16) . . ?
C12 C11 C10 120.00(16) . . ?
C11 C12 C13 120.81(18) . . ?
C14 C13 C12 120.06(17) . . ?
C13 C14 C15 120.89(16) . . ?
C14 C15 C10 118.75(16) . . ?
C16 C15 C10 117.85(16) . . ?
C16 C15 C14 123.40(16) . . ?
C17 C16 C15 119.73(16) . . ?
C16 C17 C18 118.63(16) . . ?
N1 C18 C17 123.62(16) . . ?
N1 C18 C19 116.45(14) . . ?
C17 C18 C19 119.92(15) . . ?
O1 C19 C18 117.23(15) . . ?
O11 C19 O1 125.50(16) . . ?
O11 C19 C18 117.27(15) . . ?
N2 C21 C22 112.83(15) . . ?
O2 C22 C21 112.64(15) . . ?

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
_geom_hbond_publ_flag
O2 H2 O11 0.84(3) 1.95(3) 2.7742(19) 168(3) 1_565 yes
N2 H2A O11 0.83(3) 2.33(3) 3.036(2) 144(2) 1_565 yes

####################################################################### 
# 
# 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_11c
_database_code_depnum_ccdc_archive 'CCDC 2077010'
loop_
_audit_author_name
_audit_author_address
'Barbara Modec'
;University of Ljubljana
Slovenia
;
_audit_update_record             
;
2022-02-17 deposited with the CCDC.	2022-03-18 downloaded from the CCDC.
;
_audit_creation_date             2022-02-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H21 Cu N3 O5'
_chemical_formula_sum            'C23 H21 Cu N3 O5'
_chemical_formula_weight         482.97
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_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                   10.3764(5)
_cell_length_b                   7.5417(4)
_cell_length_c                   13.4913(6)
_cell_angle_alpha                90
_cell_angle_beta                 107.782(5)
_cell_angle_gamma                90
_cell_volume                     1005.33(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2211
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      75.2070
_cell_measurement_theta_min      3.4270
_shelx_estimated_absorpt_T_max   0.911
_shelx_estimated_absorpt_T_min   0.555
_exptl_absorpt_coefficient_mu    1.908
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.20627
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.595
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             498
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4037
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.373
_diffrn_reflns_theta_min         6.432
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00  26.00   1.00    1.00    --  -41.63  37.00  60.00   92
  2  ω    -86.00 -21.00   1.00    1.00    --  -41.63 -37.00-150.00   65
  3  ω     51.00  89.00   1.00    1.00    --   41.63-125.00 -90.00   38
  4  ω      5.00  41.00   1.00    1.00    --   41.63 -99.00-180.00   36
  5  ω    134.00 178.00   1.00    1.50    --  109.50 125.00-180.00   44
  6  ω     52.00 106.00   1.00    1.50    --  109.50 -94.00 -90.00   54
  7  ω     36.00  96.00   1.00    1.50    --  109.50 -94.00 120.00   60
  8  ω    124.00 174.00   1.00    1.50    --  109.50  61.00-150.00   50
  9  ω     96.00 121.00   1.00    1.50    --  109.50  61.00-150.00   25
 10  ω     41.00 101.00   1.00    1.50    --  109.50-106.00-150.00   60
 11  ω     81.00 162.00   1.00    1.50    --  109.50  61.00 -30.00   81
 12  ω     42.00  71.00   1.00    1.50    --  109.50 -94.00 -30.00   29
 13  ω     94.00 152.00   1.00    1.50    --  109.50 125.00 150.00   58
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1364240000
_diffrn_orient_matrix_UB_12      0.0385869000
_diffrn_orient_matrix_UB_13      0.0188089000
_diffrn_orient_matrix_UB_21      0.0434110000
_diffrn_orient_matrix_UB_22      0.1942848000
_diffrn_orient_matrix_UB_23      0.0260660000
_diffrn_orient_matrix_UB_31      -0.0618738000
_diffrn_orient_matrix_UB_32      0.0503120000
_diffrn_orient_matrix_UB_33      -0.1154347000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1830
_reflns_number_total             2013
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.464
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       0.0019(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     171
_refine_ls_number_reflns         2013
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0373
_refine_ls_R_factor_gt           0.0345
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0549P)²+0.6096P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0946
_refine_ls_wR_factor_ref         0.0974
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Others
 Fixed Sof: O2(0.5) H2(0.5) N2(0.5) H2A(0.5) H2B(0.5) C21(0.5) H21A(0.5)
 H21B(0.5) C22(0.5) H22A(0.5) H22B(0.5) C23(0.5) H23A(0.5) H23B(0.5)
3.a Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B), C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B)
3.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17)
3.c Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.500000 0.000000 0.500000 0.01454(16) Uani 1 2 d S T P . .
O1 O 0.56092(14) 0.0583(2) 0.64755(9) 0.0215(3) Uani 1 1 d . . . . .
O11 O 0.71480(15) 0.1918(2) 0.77688(11) 0.0331(4) Uani 1 1 d . . . . .
N1 N 0.70761(16) 0.1082(2) 0.51869(12) 0.0210(3) Uani 1 1 d . . . . .
C10 C 0.7826(2) 0.1267(3) 0.45107(15) 0.0235(4) Uani 1 1 d . . . . .
C11 C 0.7332(2) 0.0520(3) 0.35018(16) 0.0285(5) Uani 1 1 d . . . . .
H11 H 0.649768 -0.005016 0.329505 0.034 Uiso 1 1 calc R . . . .
C12 C 0.8093(2) 0.0642(4) 0.28296(16) 0.0326(5) Uani 1 1 d . . . . .
H12 H 0.777857 0.012735 0.217321 0.039 Uiso 1 1 calc R . . . .
C13 C 0.9345(2) 0.1541(3) 0.31259(17) 0.0338(5) Uani 1 1 d . . . . .
H13 H 0.984105 0.162846 0.265858 0.041 Uiso 1 1 calc R . . . .
C14 C 0.9835(2) 0.2282(3) 0.40874(18) 0.0310(5) Uani 1 1 d . . . . .
H14 H 1.065753 0.288079 0.426893 0.037 Uiso 1 1 calc R . . . .
C15 C 0.9098(2) 0.2147(3) 0.48174(16) 0.0266(4) Uani 1 1 d . . . . .
C16 C 0.9571(2) 0.2833(3) 0.58352(18) 0.0313(5) Uani 1 1 d . . . . .
H16 H 1.039038 0.343906 0.605289 0.038 Uiso 1 1 calc R . . . .
C17 C 0.8824(2) 0.2607(3) 0.65022(16) 0.0289(5) Uani 1 1 d . . . . .
H17 H 0.913023 0.304124 0.717902 0.035 Uiso 1 1 calc R . . . .
C18 C 0.75841(19) 0.1704(3) 0.61445(14) 0.0214(4) Uani 1 1 d . . . . .
C19 C 0.67337(19) 0.1379(3) 0.68667(14) 0.0217(4) Uani 1 1 d . . . . .
O2 O 0.5864(5) 0.7226(7) 0.5461(4) 0.0224(10) Uani 0.5 1 d . . . A -1
H2 H 0.606172 0.825561 0.537611 0.034 Uiso 0.5 1 calc GR . . A -1
N2 N 0.3927(6) 0.2371(8) 0.4786(4) 0.0216(11) Uani 0.5 1 d . . . A -1
H2A H 0.353130 0.248752 0.410442 0.026 Uiso 0.5 1 calc R . . A -1
H2B H 0.326567 0.222786 0.507160 0.026 Uiso 0.5 1 calc R . . A -1
C21 C 0.4556(6) 0.4038(6) 0.5152(3) 0.0335(10) Uani 0.5 1 d . . . A -1
H21A H 0.525346 0.388152 0.581465 0.040 Uiso 0.5 1 calc R . . A -1
H21B H 0.388978 0.486679 0.524960 0.040 Uiso 0.5 1 calc R . . A -1
C22 C 0.5187(5) 0.4764(6) 0.4327(4) 0.0296(9) Uani 0.5 1 d . . . A -1
H22A H 0.553111 0.377954 0.401976 0.035 Uiso 0.5 1 calc R . . A -1
H22B H 0.448870 0.534750 0.377758 0.035 Uiso 0.5 1 calc R . . A -1
C23 C 0.6342(4) 0.6081(5) 0.4796(3) 0.0166(7) Uani 0.5 1 d . . . A -1
H23A H 0.715410 0.545949 0.519419 0.020 Uiso 0.5 1 calc R . . A -1
H23B H 0.654557 0.675946 0.425172 0.020 Uiso 0.5 1 calc R . . A -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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.9460(12) . ?
Cu1 O1 1.9461(12) 3_656 ?
Cu1 N1 2.2447(17) 3_656 ?
Cu1 N1 2.2447(17) . ?
Cu1 N2 2.079(6) . ?
O1 C19 1.274(2) . ?
O11 C19 1.230(2) . ?
N1 C10 1.375(2) . ?
N1 C18 1.323(2) . ?
C10 C11 1.416(3) . ?
C10 C15 1.422(3) . ?
C11 C12 1.375(3) . ?
C12 C13 1.411(3) . ?
C13 C14 1.360(3) . ?
C14 C15 1.423(3) . ?
C15 C16 1.408(3) . ?
C16 C17 1.366(3) . ?
C17 C18 1.405(3) . ?
C18 C19 1.521(3) . ?
O2 C23 1.438(6) . ?
N2 C21 1.433(7) . ?
C21 C22 1.553(6) . ?
C22 C23 1.537(6) . ?

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 Cu1 O1 180.0 . 3_656 ?
O1 Cu1 N1 101.41(6) . 3_656 ?
O1 Cu1 N1 78.59(6) 3_656 3_656 ?
O1 Cu1 N1 78.59(6) . . ?
O1 Cu1 N1 101.41(6) 3_656 . ?
O1 Cu1 N2 86.58(17) . . ?
O1 Cu1 N2 93.42(17) 3_656 . ?
N1 Cu1 N1 180.0 . 3_656 ?
N2 Cu1 N1 99.08(16) . . ?
N2 Cu1 N1 80.92(16) . 3_656 ?
C19 O1 Cu1 120.02(12) . . ?
C10 N1 Cu1 132.87(13) . . ?
C18 N1 Cu1 108.72(12) . . ?
C18 N1 C10 118.34(17) . . ?
N1 C10 C11 119.05(19) . . ?
N1 C10 C15 121.16(18) . . ?
C11 C10 C15 119.76(18) . . ?
C12 C11 C10 119.7(2) . . ?
C11 C12 C13 120.6(2) . . ?
C14 C13 C12 120.74(19) . . ?
C13 C14 C15 120.5(2) . . ?
C10 C15 C14 118.64(19) . . ?
C16 C15 C10 118.13(18) . . ?
C16 C15 C14 123.2(2) . . ?
C17 C16 C15 119.8(2) . . ?
C16 C17 C18 118.62(19) . . ?
N1 C18 C17 123.86(18) . . ?
N1 C18 C19 115.61(17) . . ?
C17 C18 C19 120.53(17) . . ?
O1 C19 C18 116.59(16) . . ?
O11 C19 O1 124.39(18) . . ?
O11 C19 C18 119.01(17) . . ?
C21 N2 Cu1 122.6(4) . . ?
N2 C21 C22 108.0(4) . . ?
C23 C22 C21 112.3(4) . . ?
O2 C23 C22 105.7(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
_geom_hbond_publ_flag
N2 H2A O11 0.89 1.98 2.835(6) 160.0 4_565 yes

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.372
_oxdiff_exptl_absorpt_empirical_full_min 0.535
####################################################################### 
# 
# 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_11b
_database_code_depnum_ccdc_archive 'CCDC 2077009'
loop_
_audit_author_name
_audit_author_address
'Barbara Modec'
;University of Ljubljana
Slovenia
;
_audit_update_record             
;
2022-02-17 deposited with the CCDC.	2022-03-18 downloaded from the CCDC.
;
_audit_creation_date             2022-02-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H21 Cu N3 O5'
_chemical_formula_sum            'C23 H21 Cu N3 O5'
_chemical_formula_weight         482.97
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   13.8822(4)
_cell_length_b                   8.3669(2)
_cell_length_c                   18.7238(5)
_cell_angle_alpha                90
_cell_angle_beta                 111.589(3)
_cell_angle_gamma                90
_cell_volume                     2022.22(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2519
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      74.8650
_cell_measurement_theta_min      3.3970
_shelx_estimated_absorpt_T_max   0.703
_shelx_estimated_absorpt_T_min   0.451
_exptl_absorpt_coefficient_mu    1.897
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.31275
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             996
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0148
_diffrn_reflns_av_unetI/netI     0.0159
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            3761
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.955
_diffrn_reflns_theta_min         5.867
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      3.00  33.00   1.00    1.00    --  -41.63  37.00 -30.00   30
  2  ω   -115.00 -15.00   1.00    1.00    --  -41.63 -57.00-180.00  100
  3  ω    -51.00   0.00   1.00    1.00    --  -41.63  37.00 -30.00   51
  4  ω    -70.00 -44.00   1.00    1.00    --  -41.63-169.00 -44.00   26
  5  ω     84.00 169.00   1.00    3.00    --  109.50  30.00 150.00   85
  6  ω     42.00 110.00   1.00    3.00    --  109.50-125.00 -90.00   68
  7  ω     49.00 107.00   1.00    3.00    --  109.50 -94.00 -30.00   58
  8  ω    127.00 176.00   1.00    3.00    --  109.50 125.00  30.00   49
  9  ω    108.00 134.00   1.00    3.00    --  109.50 125.00-120.00   26
 10  ω     94.00 121.00   1.00    3.00    --  109.50 125.00  30.00   27
 11  ω     44.00  69.00   1.00    3.00    --  109.50 -94.00-180.00   25
 12  ω     36.00 126.00   1.00    3.00    --  109.50 -45.00 -30.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0242079000
_diffrn_orient_matrix_UB_12      0.0517967000
_diffrn_orient_matrix_UB_13      -0.0705284000
_diffrn_orient_matrix_UB_21      0.1149344000
_diffrn_orient_matrix_UB_22      0.0212276000
_diffrn_orient_matrix_UB_23      0.0513249000
_diffrn_orient_matrix_UB_31      0.0211407000
_diffrn_orient_matrix_UB_32      -0.1754828000
_diffrn_orient_matrix_UB_33      -0.0146490000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1975
_reflns_number_total             2028
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       0.0040(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2028
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0322
_refine_ls_restrained_S_all      1.076
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0545P)²+2.2685P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0896
_refine_ls_wR_factor_ref         0.0904
_refine_special_details          ?
_olex2_refinement_description    
;
1. Uiso/Uaniso restraints and constraints
C21 \\sim C23: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.002
Uanis(C22) \\sim Ueq: with sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(C21) = Uanis(C23)
2. Others
 Fixed Sof: O2(0.5) H2(0.5) N2(0.5) H2A(0.5) H2B(0.5) C21(0.5) H21A(0.5)
 H21B(0.5) C22(0.5) H22A(0.5) H22B(0.5) C23(0.5) H23A(0.5) H23B(0.5)
 Fixed U12: Cu1(-0)
 Fixed U23: Cu1(0)
 Fixed Uiso: H11(0.039) H12(0.049) H13(0.049) H14(0.043) H16(0.033) H17(0.028)
 H2(0.031) H2A(0.023) H2B(0.023) H21A(0.026) H21B(0.026) H22A(0.025)
 H22B(0.025) H23A(0.026) H23B(0.026)
 Fixed X: Cu1(0.75) H11(0.91038) H12(1.01059) H13(0.939749) H14(0.7685)
 H16(0.594709) H17(0.495609) H2(0.81256) H2A(0.685881) H2B(0.775009)
 H21A(0.83017) H21B(0.87624) H22A(0.79802) H22B(0.7009) H23A(0.63159)
 H23B(0.675361)
 Fixed Y: H11(0.294449) H12(0.1742) H13(-0.0115) H14(-0.078179) H16(-0.041019)
 H17(0.09155) H2(0.67287) H2A(0.63227) H2B(0.56554) H21A(0.80719)
 H21B(0.721371) H22A(0.935109) H22B(0.90936) H23A(0.715) H23B(0.839509)
 Fixed Z: Cu1(0.5) H11(0.65931) H12(0.772789) H13(0.83182) H14(0.77734)
 H16(0.670321) H17(0.55979) H2(0.416149) H2A(0.55717) H2B(0.615761)
 H21A(0.615181) H21B(0.56023) H22A(0.496889) H22B(0.51922) H23A(0.42588)
 H23B(0.38327)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.750000 0.42499(4) 0.500000 0.02099(16) Uani 1 2 d S T P . .
O1 O 0.59942(9) 0.41703(13) 0.45421(6) 0.0199(3) Uani 1 1 d . . . . .
O11 O 0.45803(9) 0.28333(16) 0.44801(7) 0.0261(3) Uani 1 1 d . . . . .
N1 N 0.71495(10) 0.25656(16) 0.58029(7) 0.0179(3) Uani 1 1 d . . . . .
C10 C 0.77462(13) 0.1822(2) 0.64756(9) 0.0223(3) Uani 1 1 d . . . . .
C11 C 0.88089(14) 0.2205(3) 0.68229(10) 0.0329(4) Uani 1 1 d . . . . .
H11 H 0.910380 0.294449 0.659310 0.039 Uiso 1 1 d . . . . .
C12 C 0.94073(15) 0.1482(3) 0.75020(10) 0.0407(5) Uani 1 1 d . . . . .
H12 H 1.010590 0.174200 0.772789 0.049 Uiso 1 1 d . . . . .
C13 C 0.89815(18) 0.0360(3) 0.78592(10) 0.0407(5) Uani 1 1 d . . . . .
H13 H 0.939749 -0.011500 0.831820 0.049 Uiso 1 1 d . . . . .
C14 C 0.79604(17) -0.0032(3) 0.75346(11) 0.0356(5) Uani 1 1 d . . . . .
H14 H 0.768500 -0.078179 0.777340 0.043 Uiso 1 1 d . . . . .
C15 C 0.73075(15) 0.0688(2) 0.68348(10) 0.0257(4) Uani 1 1 d . . . . .
C16 C 0.62491(15) 0.0346(2) 0.64867(10) 0.0277(4) Uani 1 1 d . . . . .
H16 H 0.594709 -0.041019 0.670321 0.033 Uiso 1 1 d . . . . .
C17 C 0.56616(13) 0.1121(2) 0.58300(10) 0.0231(3) Uani 1 1 d . . . . .
H17 H 0.495609 0.091550 0.559790 0.028 Uiso 1 1 d . . . . .
C18 C 0.61473(12) 0.22421(18) 0.55103(8) 0.0168(3) Uani 1 1 d . . . . .
C19 C 0.55082(12) 0.31460(19) 0.47861(8) 0.0176(3) Uani 1 1 d . . . . .
O2 O 0.7537(3) 0.6402(4) 0.4076(2) 0.0206(7) Uani 0.5 1 d . . . A -1
H2 H 0.812560 0.672870 0.416149 0.031 Uiso 0.5 1 d . . . B -1
N2 N 0.7513(3) 0.6030(5) 0.5679(2) 0.0193(8) Uani 0.5 1 d . . . A -1
H2A H 0.685881 0.632270 0.557170 0.023 Uiso 0.5 1 d . . . C -1
H2B H 0.775009 0.565540 0.615761 0.023 Uiso 0.5 1 d . . . D -1
C21 C 0.8123(11) 0.7527(8) 0.5647(9) 0.019(2) Uani 0.5 1 d . U . A -1
H21A H 0.830170 0.807190 0.615181 0.026 Uiso 0.5 1 d . . . E -1
H21B H 0.876240 0.721371 0.560230 0.026 Uiso 0.5 1 d . . . F -1
C22 C 0.7517(11) 0.8546(3) 0.5050(6) 0.0205(8) Uani 0.5 1 d . U . A -1
H22A H 0.798020 0.935109 0.496889 0.025 Uiso 0.5 1 d . . . G -1
H22B H 0.700900 0.909360 0.519220 0.025 Uiso 0.5 1 d . . . H -1
C23 C 0.6948(11) 0.7604(8) 0.4227(9) 0.019(2) Uani 0.5 1 d . U . A -1
H23A H 0.631590 0.715000 0.425880 0.026 Uiso 0.5 1 d . . . I -1
H23B H 0.675361 0.839509 0.383270 0.026 Uiso 0.5 1 d . . . J -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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.9468(11) . ?
Cu1 O1 1.9468(11) 2_656 ?
Cu1 N1 2.2408(13) . ?
Cu1 N1 2.2408(13) 2_656 ?
Cu1 O2 2.510(4) . ?
Cu1 N2 1.953(4) . ?
O1 C19 1.275(2) . ?
O11 C19 1.230(2) . ?
N1 C10 1.375(2) . ?
N1 C18 1.322(2) . ?
C10 C11 1.413(3) . ?
C10 C15 1.423(2) . ?
C11 C12 1.377(3) . ?
C12 C13 1.403(4) . ?
C13 C14 1.361(3) . ?
C14 C15 1.424(2) . ?
C15 C16 1.400(3) . ?
C16 C17 1.364(3) . ?
C17 C18 1.411(2) . ?
C18 C19 1.521(2) . ?
O2 C23 1.388(15) . ?
N2 C21 1.525(13) . ?
C21 C22 1.411(17) . ?
C22 C23 1.651(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 176.08(7) . 2_656 ?
O1 Cu1 N1 98.40(5) . 2_656 ?
O1 Cu1 N1 79.10(5) 2_656 2_656 ?
O1 Cu1 N1 79.10(5) . . ?
O1 Cu1 N1 98.40(5) 2_656 . ?
O1 Cu1 O2 90.68(8) . . ?
O1 Cu1 O2 92.13(8) 2_656 . ?
O1 Cu1 N2 89.32(13) 2_656 . ?
O1 Cu1 N2 93.67(13) . . ?
N1 Cu1 N1 102.07(7) . 2_656 ?
N1 Cu1 O2 167.93(9) . . ?
N1 Cu1 O2 85.65(8) 2_656 . ?
N2 Cu1 N1 164.47(13) . 2_656 ?
N2 Cu1 N1 89.74(13) . . ?
N2 Cu1 O2 84.47(11) . . ?
C19 O1 Cu1 119.29(10) . . ?
C10 N1 Cu1 133.83(11) . . ?
C18 N1 Cu1 107.81(10) . . ?
C18 N1 C10 118.31(14) . . ?
N1 C10 C11 119.61(16) . . ?
N1 C10 C15 121.07(16) . . ?
C11 C10 C15 119.31(16) . . ?
C12 C11 C10 119.9(2) . . ?
C11 C12 C13 121.1(2) . . ?
C14 C13 C12 120.04(17) . . ?
C13 C14 C15 120.97(19) . . ?
C10 C15 C14 118.61(18) . . ?
C16 C15 C10 118.33(16) . . ?
C16 C15 C14 123.05(17) . . ?
C17 C16 C15 119.95(16) . . ?
C16 C17 C18 118.58(16) . . ?
N1 C18 C17 123.69(15) . . ?
N1 C18 C19 116.58(13) . . ?
C17 C18 C19 119.73(14) . . ?
O1 C19 C18 116.22(13) . . ?
O11 C19 O1 125.29(15) . . ?
O11 C19 C18 118.49(14) . . ?
C23 O2 Cu1 102.5(5) . . ?
C21 N2 Cu1 118.3(6) . . ?
C22 C21 N2 110.4(10) . . ?
C21 C22 C23 113.1(4) . . ?
O2 C23 C22 114.9(10) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O11 0.820(3) 1.9188(11) 2.730(4) 169.7(3) 6_665 yes
N2 H2A O11 0.890(4) 2.0873(12) 2.967(4) 169.8(3) 5_666 yes

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.122
_oxdiff_exptl_absorpt_empirical_full_min 0.623
####################################################################### 
# 
# 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_5e
_database_code_depnum_ccdc_archive 'CCDC 2076997'
loop_
_audit_author_name
_audit_author_address
'Barbara Modec'
;University of Ljubljana
Slovenia
;
_audit_update_record             
;
2022-02-17 deposited with the CCDC.	2022-03-18 downloaded from the CCDC.
;
_audit_creation_date             2022-02-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H27 Cu N3 O3, 2(C10 H6 N O2)'
_chemical_formula_sum            'C29 H39 Cu N5 O7'
_chemical_formula_weight         633.19
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.3197(4)
_cell_length_b                   12.5306(7)
_cell_length_c                   14.6852(7)
_cell_angle_alpha                106.796(5)
_cell_angle_beta                 94.775(4)
_cell_angle_gamma                110.018(4)
_cell_volume                     1510.64(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4137
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      74.5600
_cell_measurement_theta_min      3.9640
_shelx_estimated_absorpt_T_max   0.971
_shelx_estimated_absorpt_T_min   0.667
_exptl_absorpt_coefficient_mu    1.469
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34378
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.392
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             666
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0504
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11079
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.220
_diffrn_reflns_theta_min         3.210
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -85.00  -8.00   1.00   12.25    --  -41.76 125.00 -90.00   77
  2  ω   -107.00 -21.00   1.00   12.25    --  -41.76 -37.00   0.00   86
  3  ω    -66.00  33.00   1.00   12.25    --  -41.76  37.00-180.00   99
  4  ω     26.00 106.00   1.00   12.25    --   41.76  37.00 -90.00   80
  5  ω     58.00  93.00   1.00   12.25    --   41.76-125.00-180.00   35
  6  ω    138.00 176.00   1.00   48.00    --  109.50  61.00  60.00   38
  7  ω     83.00 120.00   1.00   48.00    --  109.50  61.00  60.00   37
  8  ω     41.00 137.00   1.00   48.00    --  109.50 -61.00 -90.00   96
  9  ω     49.00 118.00   1.00   48.00    --  109.50-125.00 120.00   69
 10  ω    110.00 165.00   1.00   48.00    --  109.50 125.00 -30.00   55
 11  ω     42.00  76.00   1.00   48.00    --  109.50 -94.00 -90.00   34
 12  ω     80.00 109.00   1.00   48.00    --  109.50 -94.00 -90.00   29
 13  ω     92.00 172.00   1.00   48.00    --  109.50  45.00 -30.00   80
 14  ω     89.00 117.00   1.00   48.00    --  109.50  45.00 150.00   28
 15  ω    110.00 153.00   1.00   48.00    --  109.50 -15.00 -60.00   43
 16  ω     42.00 117.00   1.00   48.00    --  109.50-125.00-150.00   75
 17  ω     34.00  86.00   1.00   48.00    --  109.50 -15.00 -60.00   52
 18  ω     77.00 108.00   1.00   48.00    --  109.50 -94.00-150.00   31
 19  ω     99.00 171.00   1.00   48.00    --  109.50 125.00-120.00   72
 20  ω     78.00 105.00   1.00   48.00    --  109.50 -94.00   0.00   27
 21  ω     95.00 149.00   1.00   48.00    --  109.50 125.00   0.00   54
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0373019000
_diffrn_orient_matrix_UB_12      -0.1032570000
_diffrn_orient_matrix_UB_13      0.0422999000
_diffrn_orient_matrix_UB_21      -0.0602830000
_diffrn_orient_matrix_UB_22      -0.0931812000
_diffrn_orient_matrix_UB_23      -0.1035341000
_diffrn_orient_matrix_UB_31      0.1650751000
_diffrn_orient_matrix_UB_32      0.0007703000
_diffrn_orient_matrix_UB_33      -0.0035879000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4803
_reflns_number_total             6067
_reflns_odcompleteness_completeness 99.88
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.619
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     449
_refine_ls_number_reflns         6067
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0452
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0650P)²+0.3434P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1121
_refine_ls_wR_factor_ref         0.1234
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C22A) = Uanis(C23A) = Uanis(C23) = Uanis(C22)
3. Others
 Sof(C31A)=Sof(H31C)=Sof(H31D)=Sof(C32A)=Sof(H32A)=Sof(C33A)=Sof(H33D)=
 Sof(H33E)=Sof(H33F)=1-FVAR(1)
 Sof(C31)=Sof(H31A)=Sof(H31B)=Sof(C32)=Sof(H32)=Sof(C33)=Sof(H33A)=Sof(H33B)=
 Sof(H33C)=FVAR(1)
 Sof(H21C)=Sof(H21D)=Sof(C22A)=Sof(H22A)=Sof(C23A)=Sof(H23D)=Sof(H23E)=
 Sof(H23F)=1-FVAR(2)
 Sof(H21A)=Sof(H21B)=Sof(C22)=Sof(H22)=Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(H23C)=
 FVAR(2)
4.a Ternary CH refined with riding coordinates:
 C12(H12), C22(H22), C32(H32), C22A(H22A), C32A(H32A)
4.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C21(H21A,H21B), C21(H21C,H21D), C31(H31A,H31B), C31A(H31C,H31D)
4.c Aromatic/amide H refined with riding coordinates:
 C41(H41), C42(H42), C43(H43), C44(H44), C46(H46), C47(H47), C51(H51),
 C52(H52), C53(H53), C54(H54), C56(H56), C57(H57)
4.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C23(H23A,H23B,H23C), C33(H33A,H33B,H33C), C23A(H23D,H23E,
 H23F), C33A(H33D,H33E,H33F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.65806(4) 0.28143(3) 0.50258(3) 0.02806(11) Uani 1 1 d . . . . .
O1 O 0.7632(2) 0.14563(18) 0.40843(14) 0.0351(4) Uani 1 1 d . . . . .
H1 H 0.801(4) 0.173(3) 0.374(2) 0.029(8) Uiso 1 1 d . . . . .
O2 O 0.5817(2) 0.39448(17) 0.63652(15) 0.0389(4) Uani 1 1 d . . . . .
H2 H 0.652(5) 0.455(4) 0.670(3) 0.065(12) Uiso 1 1 d . . . . .
O3 O 0.4882(2) 0.26036(19) 0.39690(16) 0.0445(5) Uani 1 1 d . . . . .
H3 H 0.418(5) 0.190(4) 0.361(3) 0.075(13) Uiso 1 1 d . . . . .
O4 O 0.3135(2) -0.05236(18) 0.35943(14) 0.0423(4) Uani 1 1 d . . . . .
O5 O 0.8457(2) 0.5740(2) 0.74745(16) 0.0539(6) Uani 1 1 d . . . . .
O44 O 0.2703(2) 0.06753(18) 0.28328(16) 0.0445(5) Uani 1 1 d . . . . .
O55 O 0.9804(2) 0.6190(2) 0.63658(16) 0.0564(6) Uani 1 1 d . . . . .
N1 N 0.8495(2) 0.3079(2) 0.59982(16) 0.0316(4) Uani 1 1 d . . . . .
H1A H 0.888(4) 0.379(4) 0.631(3) 0.050(10) Uiso 1 1 d . . . . .
H1B H 0.824(3) 0.267(3) 0.638(2) 0.028(7) Uiso 1 1 d . . . . .
N2 N 0.5108(3) 0.14921(19) 0.53912(17) 0.0326(4) Uani 1 1 d . . . . .
H2A H 0.451(4) 0.092(3) 0.484(3) 0.037(8) Uiso 1 1 d . . . . .
H2B H 0.562(3) 0.123(3) 0.566(2) 0.029(7) Uiso 1 1 d . . . . .
N3 N 0.7764(2) 0.4215(2) 0.46333(18) 0.0354(5) Uani 1 1 d . . . . .
H3A H 0.834(4) 0.485(4) 0.516(3) 0.052(10) Uiso 1 1 d . . . . .
H3B H 0.840(4) 0.400(3) 0.432(3) 0.052(10) Uiso 1 1 d . . . . .
N4 N 0.0938(2) -0.24647(19) 0.21165(15) 0.0314(4) Uani 1 1 d . . . . .
N5 N 1.1776(2) 0.83257(18) 0.77309(15) 0.0288(4) Uani 1 1 d . . . . .
C11 C 0.9643(3) 0.2679(2) 0.5519(2) 0.0359(5) Uani 1 1 d . . . . .
H11A H 1.039204 0.264425 0.599817 0.043 Uiso 1 1 calc R . . . .
H11B H 1.020470 0.325577 0.522534 0.043 Uiso 1 1 calc R . . . .
C12 C 0.8837(3) 0.1453(2) 0.4750(2) 0.0360(5) Uani 1 1 d . . . . .
H12 H 0.834696 0.087872 0.507329 0.043 Uiso 1 1 calc R . . . .
C13 C 0.9991(4) 0.1028(3) 0.4219(2) 0.0504(7) Uani 1 1 d . . . . .
H13A H 0.943205 0.026656 0.371113 0.076 Uiso 1 1 calc GR . . . .
H13B H 1.071049 0.093849 0.466923 0.076 Uiso 1 1 calc GR . . . .
H13C H 1.055314 0.161330 0.394204 0.076 Uiso 1 1 calc GR . . . .
C21 C 0.4172(3) 0.1924(3) 0.6054(2) 0.0458(7) Uani 1 1 d . . . . .
H21A H 0.365095 0.131089 0.632696 0.055 Uiso 0.892(5) 1 calc R . P A 1
H21B H 0.338050 0.207485 0.569839 0.055 Uiso 0.892(5) 1 calc R . P A 1
H21C H 0.409331 0.151268 0.652637 0.055 Uiso 0.108(5) 1 calc R . P A 2
H21D H 0.312768 0.163832 0.567495 0.055 Uiso 0.108(5) 1 calc R . P A 2
C40 C -0.0299(3) -0.3413(2) 0.14539(19) 0.0323(5) Uani 1 1 d . . . . .
C41 C -0.0362(3) -0.4598(3) 0.1289(2) 0.0416(6) Uani 1 1 d . . . . .
H41 H 0.041212 -0.472722 0.163127 0.050 Uiso 1 1 calc R . . . .
C42 C -0.1565(3) -0.5555(3) 0.0623(3) 0.0493(7) Uani 1 1 d . . . . .
H42 H -0.160455 -0.633372 0.051798 0.059 Uiso 1 1 calc R . . . .
C43 C -0.2743(4) -0.5380(3) 0.0096(3) 0.0510(7) Uani 1 1 d . . . . .
H43 H -0.354868 -0.604203 -0.035511 0.061 Uiso 1 1 calc R . . . .
C44 C -0.2716(3) -0.4248(3) 0.0240(2) 0.0433(6) Uani 1 1 d . . . . .
H44 H -0.349737 -0.413924 -0.011346 0.052 Uiso 1 1 calc R . . . .
C45 C -0.1492(3) -0.3237(2) 0.09320(19) 0.0337(5) Uani 1 1 d . . . . .
C46 C -0.1412(3) -0.2044(2) 0.1131(2) 0.0350(5) Uani 1 1 d . . . . .
H46 H -0.219935 -0.189558 0.082199 0.042 Uiso 1 1 calc R . . . .
C47 C -0.0171(3) -0.1109(2) 0.17804(19) 0.0314(5) Uani 1 1 d . . . . .
H47 H -0.009172 -0.031731 0.190997 0.038 Uiso 1 1 calc R . . . .
C48 C 0.0992(2) -0.1363(2) 0.22531(17) 0.0286(5) Uani 1 1 d . . . . .
C49 C 0.2402(3) -0.0324(2) 0.29599(18) 0.0319(5) Uani 1 1 d . . . . .
C50 C 1.2789(3) 0.9371(2) 0.84375(18) 0.0279(4) Uani 1 1 d . . . . .
C51 C 1.4123(3) 1.0120(2) 0.8196(2) 0.0342(5) Uani 1 1 d . . . . .
H51 H 1.428274 0.991526 0.756252 0.041 Uiso 1 1 calc R . . . .
C52 C 1.5171(3) 1.1141(2) 0.8896(2) 0.0388(6) Uani 1 1 d . . . . .
H52 H 1.604577 1.162543 0.873564 0.047 Uiso 1 1 calc R . . . .
C53 C 1.4945(3) 1.1470(2) 0.9858(2) 0.0400(6) Uani 1 1 d . . . . .
H53 H 1.567337 1.216588 1.032633 0.048 Uiso 1 1 calc R . . . .
C54 C 1.3666(3) 1.0776(2) 1.01097(19) 0.0379(6) Uani 1 1 d . . . . .
H54 H 1.352280 1.100279 1.074607 0.045 Uiso 1 1 calc R . . . .
C55 C 1.2556(3) 0.9712(2) 0.94013(18) 0.0314(5) Uani 1 1 d . . . . .
C56 C 1.1213(3) 0.8953(3) 0.96178(19) 0.0394(6) Uani 1 1 d . . . . .
H56 H 1.100237 0.916374 1.023822 0.047 Uiso 1 1 calc R . . . .
C57 C 1.0231(3) 0.7913(3) 0.8915(2) 0.0391(6) Uani 1 1 d . . . . .
H57 H 0.935157 0.740132 0.905237 0.047 Uiso 1 1 calc R . . . .
C58 C 1.0564(3) 0.7618(2) 0.79709(18) 0.0296(5) Uani 1 1 d . . . . .
C59 C 0.9518(3) 0.6421(2) 0.7197(2) 0.0368(5) Uani 1 1 d . . . . .
C22 C 0.5217(4) 0.3078(3) 0.6866(3) 0.0404(6) Uani 0.892(5) 1 d . . P A 1
H22 H 0.607884 0.295236 0.718866 0.049 Uiso 0.892(5) 1 calc R . P A 1
C23 C 0.4315(4) 0.3508(3) 0.7596(2) 0.0404(6) Uani 0.892(5) 1 d . . P A 1
H23A H 0.498002 0.427821 0.806167 0.061 Uiso 0.892(5) 1 calc GR . P A 1
H23B H 0.395046 0.293556 0.792362 0.061 Uiso 0.892(5) 1 calc GR . P A 1
H23C H 0.343991 0.358438 0.726732 0.061 Uiso 0.892(5) 1 calc GR . P A 1
C31 C 0.6772(6) 0.4374(4) 0.3914(4) 0.0386(11) Uani 0.648(8) 1 d . . P B 1
H31A H 0.740530 0.478608 0.353301 0.046 Uiso 0.648(8) 1 calc R . P B 1
H31B H 0.623718 0.487039 0.423657 0.046 Uiso 0.648(8) 1 calc R . P B 1
C32 C 0.5588(5) 0.3165(4) 0.3251(4) 0.0343(11) Uani 0.648(8) 1 d . . P B 1
H32 H 0.610336 0.268690 0.286285 0.041 Uiso 0.648(8) 1 calc R . P B 1
C33 C 0.4329(7) 0.3266(4) 0.2607(4) 0.0541(15) Uani 0.648(8) 1 d . . P B 1
H33A H 0.358401 0.247309 0.222990 0.081 Uiso 0.648(8) 1 calc GR . P B 1
H33B H 0.478681 0.367629 0.217883 0.081 Uiso 0.648(8) 1 calc GR . P B 1
H33C H 0.381455 0.371372 0.300049 0.081 Uiso 0.648(8) 1 calc GR . P B 1
C22A C 0.464(3) 0.329(3) 0.663(2) 0.0404(6) Uani 0.108(5) 1 d . . P A 2
H22A H 0.378266 0.356639 0.670445 0.049 Uiso 0.108(5) 1 calc R . P A 2
C23A C 0.542(3) 0.320(2) 0.754(2) 0.0404(6) Uani 0.108(5) 1 d . . P A 2
H23D H 0.620865 0.287720 0.739125 0.061 Uiso 0.108(5) 1 calc GR . P A 2
H23E H 0.465877 0.267312 0.778493 0.061 Uiso 0.108(5) 1 calc GR . P A 2
H23F H 0.589953 0.398546 0.803009 0.061 Uiso 0.108(5) 1 calc GR . P A 2
C31A C 0.6462(9) 0.4697(7) 0.4344(7) 0.0307(18) Uani 0.352(8) 1 d . . P B 2
H31C H 0.611490 0.505816 0.491634 0.037 Uiso 0.352(8) 1 calc R . P B 2
H31D H 0.687803 0.529788 0.403938 0.037 Uiso 0.352(8) 1 calc R . P B 2
C32A C 0.5141(9) 0.3619(7) 0.3650(6) 0.036(2) Uani 0.352(8) 1 d . . P B 2
H32A H 0.419203 0.378720 0.358617 0.043 Uiso 0.352(8) 1 calc R . P B 2
C33A C 0.5530(12) 0.3187(8) 0.2677(8) 0.049(3) Uani 0.352(8) 1 d . . P B 2
H33D H 0.642562 0.298216 0.275171 0.074 Uiso 0.352(8) 1 calc GR . P B 2
H33E H 0.575464 0.381417 0.239598 0.074 Uiso 0.352(8) 1 calc GR . P B 2
H33F H 0.466042 0.248724 0.225979 0.074 Uiso 0.352(8) 1 calc GR . P B 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 O1 2.4029(19) . ?
Cu1 O2 2.3862(19) . ?
Cu1 O3 2.0130(19) . ?
Cu1 N1 2.057(2) . ?
Cu1 N2 1.999(2) . ?
Cu1 N3 1.998(2) . ?
O1 C12 1.428(3) . ?
O2 C22 1.465(4) . ?
O2 C22A 1.29(3) . ?
O3 C32 1.505(6) . ?
O3 C32A 1.431(8) . ?
O4 C49 1.242(3) . ?
O5 C59 1.250(3) . ?
O44 C49 1.259(3) . ?
O55 C59 1.245(4) . ?
N1 C11 1.476(3) . ?
N2 C21 1.470(4) . ?
N3 C31 1.448(5) . ?
N3 C31A 1.607(8) . ?
N4 C40 1.376(3) . ?
N4 C48 1.318(3) . ?
N5 C50 1.374(3) . ?
N5 C58 1.322(3) . ?
C11 C12 1.505(4) . ?
C12 C13 1.530(3) . ?
C21 C22 1.519(4) . ?
C21 C22A 1.56(3) . ?
C40 C41 1.414(4) . ?
C40 C45 1.413(4) . ?
C41 C42 1.367(4) . ?
C42 C43 1.405(5) . ?
C43 C44 1.363(4) . ?
C44 C45 1.419(4) . ?
C45 C46 1.412(4) . ?
C46 C47 1.364(4) . ?
C47 C48 1.413(3) . ?
C48 C49 1.523(3) . ?
C50 C51 1.422(3) . ?
C50 C55 1.413(3) . ?
C51 C52 1.365(4) . ?
C52 C53 1.408(4) . ?
C53 C54 1.364(4) . ?
C54 C55 1.416(4) . ?
C55 C56 1.413(4) . ?
C56 C57 1.360(4) . ?
C57 C58 1.418(4) . ?
C58 C59 1.523(4) . ?
C22 C23 1.508(4) . ?
C31 C32 1.512(6) . ?
C32 C33 1.508(6) . ?
C22A C23A 1.52(4) . ?
C31A C32A 1.496(10) . ?
C32A C33A 1.497(14) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O1 161.13(7) . . ?
O3 Cu1 O1 98.48(8) . . ?
O3 Cu1 O2 97.71(9) . . ?
O3 Cu1 N1 173.20(9) . . ?
N1 Cu1 O1 77.60(8) . . ?
N1 Cu1 O2 87.15(8) . . ?
N2 Cu1 O1 91.33(8) . . ?
N2 Cu1 O2 78.81(8) . . ?
N2 Cu1 O3 90.75(9) . . ?
N2 Cu1 N1 94.87(10) . . ?
N3 Cu1 O1 95.54(9) . . ?
N3 Cu1 O2 96.21(9) . . ?
N3 Cu1 O3 82.20(9) . . ?
N3 Cu1 N1 92.59(9) . . ?
N3 Cu1 N2 170.80(10) . . ?
C12 O1 Cu1 105.88(14) . . ?
C22 O2 Cu1 102.61(16) . . ?
C22A O2 Cu1 113.4(12) . . ?
C32 O3 Cu1 109.9(2) . . ?
C32A O3 Cu1 115.1(3) . . ?
C11 N1 Cu1 112.75(16) . . ?
C21 N2 Cu1 112.31(17) . . ?
C31 N3 Cu1 111.1(2) . . ?
C31A N3 Cu1 103.8(3) . . ?
C48 N4 C40 117.8(2) . . ?
C58 N5 C50 118.5(2) . . ?
N1 C11 C12 110.4(2) . . ?
O1 C12 C11 110.5(2) . . ?
O1 C12 C13 111.1(2) . . ?
C11 C12 C13 111.7(2) . . ?
N2 C21 C22 109.9(2) . . ?
N2 C21 C22A 122.0(10) . . ?
N4 C40 C41 118.5(2) . . ?
N4 C40 C45 122.2(2) . . ?
C45 C40 C41 119.3(2) . . ?
C42 C41 C40 119.7(3) . . ?
C41 C42 C43 121.0(3) . . ?
C44 C43 C42 120.6(3) . . ?
C43 C44 C45 119.8(3) . . ?
C40 C45 C44 119.6(2) . . ?
C46 C45 C40 117.8(2) . . ?
C46 C45 C44 122.6(2) . . ?
C47 C46 C45 119.5(2) . . ?
C46 C47 C48 119.0(2) . . ?
N4 C48 C47 123.6(2) . . ?
N4 C48 C49 117.1(2) . . ?
C47 C48 C49 119.3(2) . . ?
O4 C49 O44 126.3(2) . . ?
O4 C49 C48 118.8(2) . . ?
O44 C49 C48 114.9(2) . . ?
N5 C50 C51 119.0(2) . . ?
N5 C50 C55 121.9(2) . . ?
C55 C50 C51 119.0(2) . . ?
C52 C51 C50 119.9(2) . . ?
C51 C52 C53 120.9(2) . . ?
C54 C53 C52 120.6(2) . . ?
C53 C54 C55 120.0(3) . . ?
C50 C55 C54 119.6(2) . . ?
C50 C55 C56 117.7(2) . . ?
C56 C55 C54 122.6(2) . . ?
C57 C56 C55 119.7(2) . . ?
C56 C57 C58 119.1(2) . . ?
N5 C58 C57 122.9(2) . . ?
N5 C58 C59 117.8(2) . . ?
C57 C58 C59 119.3(2) . . ?
O5 C59 C58 115.7(2) . . ?
O55 C59 O5 125.8(3) . . ?
O55 C59 C58 118.5(2) . . ?
O2 C22 C21 104.0(3) . . ?
O2 C22 C23 110.9(3) . . ?
C23 C22 C21 111.4(3) . . ?
N3 C31 C32 110.4(4) . . ?
O3 C32 C31 101.8(4) . . ?
O3 C32 C33 109.3(4) . . ?
C33 C32 C31 113.3(4) . . ?
O2 C22A C21 110.9(17) . . ?
O2 C22A C23A 102(2) . . ?
C23A C22A C21 93(2) . . ?
C32A C31A N3 106.2(6) . . ?
O3 C32A C31A 109.9(6) . . ?
O3 C32A C33A 102.1(7) . . ?
C31A C32A C33A 112.2(7) . . ?

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
_geom_hbond_publ_flag
O1 H1 N5 0.73(3) 2.18(3) 2.837(3) 151(3) 2_766 yes
O2 H2 O5 0.79(4) 1.90(4) 2.681(3) 166(4) . yes
O3 H3 O44 0.87(5) 1.68(5) 2.548(3) 170(5) . yes
N2 H2A O4 0.89(4) 2.09(4) 2.981(3) 175(3) . yes
N2 H2B O4 0.80(3) 2.10(3) 2.894(3) 177(3) 2_656 yes
N3 H3A O55 0.89(4) 2.03(4) 2.923(3) 174(3) . yes
N3 H3B O55 0.85(4) 2.07(4) 2.908(3) 170(4) 2_766 yes

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.845
_oxdiff_exptl_absorpt_empirical_full_min 0.541
####################################################################### 
# 
# 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_7a
_database_code_depnum_ccdc_archive 'CCDC 2076999'
loop_
_audit_author_name
_audit_author_address
'Barbara Modec'
;University of Ljubljana
Slovenia
;
_audit_update_record             
;
2022-02-17 deposited with the CCDC.	2022-03-18 downloaded from the CCDC.
;
_audit_creation_date             2022-02-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H34 Cu N4 O6'
_chemical_formula_sum            'C28 H34 Cu N4 O6'
_chemical_formula_weight         586.13
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.8410(3)
_cell_length_b                   9.7548(4)
_cell_length_c                   11.6529(5)
_cell_angle_alpha                92.222(4)
_cell_angle_beta                 91.154(4)
_cell_angle_gamma                91.002(4)
_cell_volume                     663.21(5)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    4388
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      75.0340
_cell_measurement_theta_min      3.7280
_shelx_estimated_absorpt_T_max   0.954
_shelx_estimated_absorpt_T_min   0.403
_exptl_absorpt_coefficient_mu    1.587
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.17968
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             307
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11209
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.232
_diffrn_reflns_theta_min         3.797
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      1.00  26.00   1.00    1.00    --   38.00  90.00-174.86   25
  2  ω    -44.00 -15.00   1.00    1.00    --  -41.76 -57.00 -60.00   29
  3  ω    -82.00 -52.00   1.00    1.00    --  -41.76 -57.00 -60.00   30
  4  ω    -66.00  23.00   1.00    1.00    --  -41.76  37.00  30.00   89
  5  ω    -70.00  30.00   1.00    1.00    --  -41.76  57.00 120.00  100
  6  ω     19.00  62.00   1.00    1.00    --   41.76  37.00  60.00   43
  7  ω     23.00  94.00   1.00    1.00    --   41.76-125.00 -90.00   71
  8  ω     66.00 115.00   1.00    1.00    --   41.76  37.00  60.00   49
  9  ω     11.00  36.00   1.00    1.00    --   46.00  84.00 128.73   25
 10  ω     11.00  37.00   1.00    1.00    --   46.00  84.00-143.99   26
 11  ω     13.00  38.00   1.00    1.00    --   46.00  80.00  69.91   25
 12  ω     16.00  44.00   1.00    1.00    --   50.00  82.00 -62.73   28
 13  ω     17.00  42.00   1.00    1.00    --   50.00  80.00 156.78   25
 14  ω     16.00  41.00   1.00    1.00    --   50.00  81.00 -30.78   25
 15  ω     24.00  61.00   1.00    1.00    --   54.00  77.00 179.44   37
 16  ω     30.00  57.00   1.00    1.00    --   62.00  77.00 162.83   27
 17  ω     31.00  58.00   1.00    1.00    --   62.00  76.00   0.95   27
 18  ω     30.00  57.00   1.00    1.00    --   62.00  76.00  87.02   27
 19  ω     67.00 111.00   1.00    1.00    --   62.00  76.00  87.02   44
 20  ω     37.00  64.00   1.00    1.00    --   70.00  77.00  11.66   27
 21  ω     37.00  75.00   1.00    1.00    --   70.00  77.00  36.32   38
 22  ω     38.00  66.00   1.00    1.00    --   70.00  75.00-120.86   28
 23  ω     45.00  71.00   1.00    1.00    --   70.00  50.00 -30.71   26
 24  ω     93.00 120.00   1.00    1.00    --   70.00  77.00  11.66   27
 25  ω     41.00  89.00   1.00    1.00    --   70.00  77.00 171.65   48
 26  ω     45.00  83.00   1.00    1.00    --   74.00  68.00-137.00   38
 27  ω    100.00 129.00   1.00    1.00    --   74.00  67.00 -33.07   29
 28  ω     46.00  94.00   1.00    1.00    --   74.00  67.00 -33.07   48
 29  ω     45.00  85.00   1.00    3.00    --   78.00  77.00  94.92   40
 30  ω     57.00  86.00   1.00    3.00    --   82.00  69.00  22.35   29
 31  ω     57.00  89.00   1.00    3.00    --   86.00  71.00 135.51   32
 32  ω     59.00  85.00   1.00    3.00    --   90.00  70.00 118.88   26
 33  ω     61.00 104.00   1.00    3.00    --   90.00  64.00-149.86   43
 34  ω     62.00  93.00   1.00    3.00    --   94.00  73.00-112.73   31
 35  ω     86.00 145.00   1.00    3.00    --  109.50  45.00-120.00   59
 36  ω    138.00 171.00   1.00    3.00    --  109.50 125.00  90.00   33
 37  ω     77.00 151.00   1.00    3.00    --  109.50  77.00 150.00   74
 38  ω     84.00 117.00   1.00    3.00    --  109.50  61.00 -60.00   33
 39  ω     29.00 107.00   1.00    3.00    --  109.50 -94.00  90.00   78
 40  ω     43.00 118.00   1.00    3.00    --  109.50-125.00  60.00   75
 41  ω    122.00 178.00   1.00    3.00    --  109.50  77.00 -90.00   56
 42  ω     77.00 117.00   1.00    3.00    --  109.50  77.00 -90.00   40
 43  ω     77.00 148.00   1.00    3.00    --  109.50  77.00 -60.00   71
 44  ω    143.00 176.00   1.00    3.00    --  109.50  61.00  60.00   33
 45  ω     84.00 176.00   1.00    3.00    --  109.50  77.00-120.00   92
 46  ω    116.00 143.00   1.00    3.00    --  109.50  77.00  30.00   27
 47  ω     82.00 142.00   1.00    3.00    --  109.50  61.00  60.00   60
 48  ω     77.00 103.00   1.00    3.00    --  109.50  77.00  30.00   26
 49  ω     33.00  96.00   1.00    3.00    --  109.50 -94.00 -90.00   63
 50  ω    141.00 177.00   1.00    3.00    --  109.50  77.00 120.00   36
 51  ω     78.00 139.00   1.00    3.00    --  109.50  77.00 120.00   61
 52  ω     77.00 178.00   1.00    3.00    --  109.50  77.00 -30.00  101
 53  ω     75.00 102.00   1.00    3.00    --  109.50 -94.00  30.00   27
 54  ω    111.00 174.00   1.00    3.00    --  109.50  77.00-180.00   63
 55  ω     32.00 109.00   1.00    3.00    --  109.50 -94.00-180.00   77
 56  ω     78.00 108.00   1.00    3.00    --  109.50  77.00-180.00   30
 57  ω     79.00 178.00   1.00    3.00    --  109.50  77.00   0.00   99
 58  ω     80.00 175.00   1.00    3.00    --  109.50  61.00  90.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0347063000
_diffrn_orient_matrix_UB_12      0.1186568000
_diffrn_orient_matrix_UB_13      -0.0817103000
_diffrn_orient_matrix_UB_21      0.1355436000
_diffrn_orient_matrix_UB_22      -0.0782136000
_diffrn_orient_matrix_UB_23      -0.0929357000
_diffrn_orient_matrix_UB_31      -0.2236919000
_diffrn_orient_matrix_UB_32      -0.0692130000
_diffrn_orient_matrix_UB_33      -0.0468869000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2412
_reflns_number_total             2699
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.95
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.446
_refine_diff_density_min         -0.550
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         2699
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0595P)²+0.1726P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0974
_refine_ls_wR_factor_ref         0.1016
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C21-C22 \\sim C21-C22A
 with sigma of 0.02
 C22-C23 \\sim C22A-C23A
 with sigma of 0.02
 C22-O2A \\sim C22A-O2
 with sigma of 0.02
 C23-C24 \\sim C23A-C24A
 with sigma of 0.02
 C23-O2A \\sim C23A-O2
 with sigma of 0.04
 C21-C23 \\sim C21-C23A
 with sigma of 0.04
 C21-O2A \\sim C21-O2
 with sigma of 0.04
 C22-C24 \\sim C22A-C24A
 with sigma of 0.04
3. Rigid body (RIGU) restrains
 C21, C22, C23, C24, O2A, C22A, C23A, C24A, O2
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Sof(H21C)=Sof(H21D)=Sof(O2A)=Sof(H2AA)=Sof(C22A)=Sof(H22A)=Sof(C23A)=
 Sof(H23C)=Sof(H23D)=Sof(C24A)=Sof(H24D)=Sof(H24E)=Sof(H24F)=1-FVAR(1)
 Sof(H21A)=Sof(H21B)=Sof(O2)=Sof(H2)=Sof(C22)=Sof(H22)=Sof(C23)=Sof(H23A)=
 Sof(H23B)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(H24C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C22(H22), C22A(H22A)
5.b Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B), C21(H21A,H21B), C21(H21C,H21D), C23(H23A,H23B), C23A(H23C,H23D)
5.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17)
5.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C24A(H24D,H24E,H24F)
5.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O2A(H2AA)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.500000 0.500000 0.500000 0.02252(14) Uani 1 2 d S T P . .
O1 O 0.2314(2) 0.60834(13) 0.43973(11) 0.0240(3) Uani 1 1 d . . . . .
O11 O 0.0461(3) 0.80497(15) 0.43142(15) 0.0374(4) Uani 1 1 d . . . . .
N1 N 0.5246(3) 0.72046(16) 0.60124(14) 0.0234(3) Uani 1 1 d . . . . .
N2 N 0.7046(3) 0.57677(16) 0.38145(13) 0.0240(3) Uani 1 1 d . . . . .
H2A H 0.741170 0.662496 0.404681 0.029 Uiso 1 1 calc R . . . .
H2B H 0.833530 0.529521 0.383081 0.029 Uiso 1 1 calc R . . . .
C10 C 0.6754(3) 0.7768(2) 0.68155(16) 0.0249(4) Uani 1 1 d . . . . .
C11 C 0.8540(3) 0.6949(2) 0.72369(18) 0.0296(4) Uani 1 1 d . . . . .
H11 H 0.865763 0.604122 0.697324 0.036 Uiso 1 1 calc R . . . .
C12 C 1.0088(4) 0.7492(2) 0.80300(19) 0.0352(5) Uani 1 1 d . . . . .
H12 H 1.125535 0.694766 0.830251 0.042 Uiso 1 1 calc R . . . .
C13 C 0.9944(4) 0.8864(3) 0.84418(19) 0.0377(5) Uani 1 1 d . . . . .
H13 H 1.102295 0.922004 0.897557 0.045 Uiso 1 1 calc R . . . .
C14 C 0.8224(4) 0.9673(2) 0.80601(19) 0.0372(5) Uani 1 1 d . . . . .
H14 H 0.813108 1.057540 0.834118 0.045 Uiso 1 1 calc R . . . .
C15 C 0.6587(4) 0.9149(2) 0.72415(18) 0.0301(4) Uani 1 1 d . . . . .
C16 C 0.4763(4) 0.9923(2) 0.6807(2) 0.0364(5) Uani 1 1 d . . . . .
H16 H 0.458144 1.082670 0.706878 0.044 Uiso 1 1 calc R . . . .
C17 C 0.3277(4) 0.9352(2) 0.60089(19) 0.0316(4) Uani 1 1 d . . . . .
H17 H 0.207367 0.985637 0.572016 0.038 Uiso 1 1 calc R . . . .
C18 C 0.3587(3) 0.79812(19) 0.56242(16) 0.0247(4) Uani 1 1 d . . . . .
C19 C 0.1988(3) 0.73299(19) 0.47108(16) 0.0248(4) Uani 1 1 d . . . . .
C21 C 0.6289(3) 0.5806(2) 0.26023(17) 0.0287(4) Uani 1 1 d D U . . .
H21A H 0.500046 0.641651 0.255002 0.034 Uiso 0.664(5) 1 calc R . . A 1
H21B H 0.575457 0.489561 0.234768 0.034 Uiso 0.664(5) 1 calc R . . A 1
H21C H 0.476201 0.617751 0.255053 0.034 Uiso 0.336(5) 1 calc R . . A 2
H21D H 0.624943 0.488688 0.225350 0.034 Uiso 0.336(5) 1 calc R . . A 2
O2 O 0.8760(4) 0.7650(2) 0.2098(2) 0.0362(7) Uani 0.664(5) 1 d D U . A 1
H2 H 0.937417 0.768493 0.273786 0.054 Uiso 0.664(5) 1 calc GR . . A 1
C22 C 0.8121(7) 0.6277(4) 0.1795(4) 0.0268(8) Uani 0.664(5) 1 d D U . A 1
H22 H 0.946241 0.569761 0.188228 0.032 Uiso 0.664(5) 1 calc R . . A 1
C23 C 0.7356(14) 0.6225(6) 0.0535(5) 0.0375(11) Uani 0.664(5) 1 d D U . A 1
H23A H 0.681232 0.530159 0.032858 0.045 Uiso 0.664(5) 1 calc R . . A 1
H23B H 0.867644 0.641333 0.007105 0.045 Uiso 0.664(5) 1 calc R . . A 1
C24 C 0.5472(15) 0.7231(13) 0.0235(9) 0.0436(17) Uani 0.664(5) 1 d D U . A 1
H24A H 0.517653 0.718142 -0.057913 0.065 Uiso 0.664(5) 1 calc GR . . A 1
H24B H 0.595904 0.814644 0.046808 0.065 Uiso 0.664(5) 1 calc GR . . A 1
H24C H 0.409914 0.699516 0.062752 0.065 Uiso 0.664(5) 1 calc GR . . A 1
O2A O 1.0282(7) 0.6211(5) 0.2044(4) 0.0339(12) Uani 0.336(5) 1 d D U . A 2
H2AA H 1.078218 0.634507 0.270253 0.051 Uiso 0.336(5) 1 calc GR . . A 2
C22A C 0.8049(14) 0.6750(10) 0.1953(7) 0.0249(15) Uani 0.336(5) 1 d D U . A 2
H22A H 0.802773 0.769630 0.226819 0.030 Uiso 0.336(5) 1 calc R . . A 2
C23A C 0.745(2) 0.6701(12) 0.0673(8) 0.039(3) Uani 0.336(5) 1 d D U . A 2
H23C H 0.730085 0.575153 0.039785 0.047 Uiso 0.336(5) 1 calc R . . A 2
H23D H 0.869081 0.712474 0.026131 0.047 Uiso 0.336(5) 1 calc R . . A 2
C24A C 0.520(3) 0.745(3) 0.0421(19) 0.054(5) Uani 0.336(5) 1 d D U . A 2
H24D H 0.499556 0.753072 -0.039358 0.081 Uiso 0.336(5) 1 calc GR . . A 2
H24E H 0.526605 0.835226 0.078587 0.081 Uiso 0.336(5) 1 calc GR . . A 2
H24F H 0.393283 0.694175 0.071371 0.081 Uiso 0.336(5) 1 calc GR . . A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 2.0355(12) 2_666 ?
Cu1 O1 2.0355(12) . ?
Cu1 N1 2.4130(16) 2_666 ?
Cu1 N1 2.4130(16) . ?
Cu1 N2 2.0033(15) 2_666 ?
Cu1 N2 2.0033(15) . ?
O1 C19 1.275(2) . ?
O11 C19 1.238(2) . ?
N1 C10 1.365(3) . ?
N1 C18 1.324(2) . ?
N2 C21 1.474(2) . ?
C10 C11 1.416(3) . ?
C10 C15 1.423(3) . ?
C11 C12 1.365(3) . ?
C12 C13 1.409(3) . ?
C13 C14 1.366(3) . ?
C14 C15 1.412(3) . ?
C15 C16 1.414(3) . ?
C16 C17 1.356(3) . ?
C17 C18 1.410(3) . ?
C18 C19 1.515(3) . ?
C21 C22 1.515(4) . ?
C21 C22A 1.590(9) . ?
O2 C22 1.414(5) . ?
C22 C23 1.525(5) . ?
C23 C24 1.531(6) . ?
O2A C22A 1.419(9) . ?
C22A C23A 1.524(9) . ?
C23A C24A 1.548(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 180.00(4) . 2_666 ?
O1 Cu1 N1 105.64(5) 2_666 . ?
O1 Cu1 N1 105.64(5) . 2_666 ?
O1 Cu1 N1 74.36(5) 2_666 2_666 ?
O1 Cu1 N1 74.36(5) . . ?
N1 Cu1 N1 180.00(7) . 2_666 ?
N2 Cu1 O1 90.91(6) . . ?
N2 Cu1 O1 90.91(6) 2_666 2_666 ?
N2 Cu1 O1 89.09(6) 2_666 . ?
N2 Cu1 O1 89.09(6) . 2_666 ?
N2 Cu1 N1 88.07(6) . . ?
N2 Cu1 N1 91.93(6) . 2_666 ?
N2 Cu1 N1 91.92(6) 2_666 . ?
N2 Cu1 N1 88.08(6) 2_666 2_666 ?
N2 Cu1 N2 180.0 . 2_666 ?
C19 O1 Cu1 122.40(12) . . ?
C10 N1 Cu1 133.12(12) . . ?
C18 N1 Cu1 108.58(12) . . ?
C18 N1 C10 118.22(16) . . ?
C21 N2 Cu1 121.01(12) . . ?
N1 C10 C11 118.80(18) . . ?
N1 C10 C15 122.13(17) . . ?
C11 C10 C15 119.07(19) . . ?
C12 C11 C10 120.0(2) . . ?
C11 C12 C13 121.0(2) . . ?
C14 C13 C12 120.3(2) . . ?
C13 C14 C15 120.4(2) . . ?
C14 C15 C10 119.22(19) . . ?
C14 C15 C16 123.6(2) . . ?
C16 C15 C10 117.14(19) . . ?
C17 C16 C15 120.16(19) . . ?
C16 C17 C18 118.91(19) . . ?
N1 C18 C17 123.43(19) . . ?
N1 C18 C19 116.58(16) . . ?
C17 C18 C19 119.98(17) . . ?
O1 C19 C18 117.93(16) . . ?
O11 C19 O1 124.43(18) . . ?
O11 C19 C18 117.64(17) . . ?
N2 C21 C22 114.4(2) . . ?
N2 C21 C22A 108.1(3) . . ?
C21 C22 C23 113.8(4) . . ?
O2 C22 C21 109.0(3) . . ?
O2 C22 C23 107.5(3) . . ?
C22 C23 C24 114.9(6) . . ?
O2A C22A C21 109.8(6) . . ?
O2A C22A C23A 105.5(7) . . ?
C23A C22A C21 109.6(8) . . ?
C22A C23A C24A 111.5(11) . . ?

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
_geom_hbond_publ_flag
N2 H2A O11 0.89 2.25 2.995(2) 141.2 1_655 yes
O2 H2 O11 0.82 1.95 2.759(3) 169.5 1_655 yes
O2A H2AA O1 0.82 2.18 2.973(5) 163.7 1_655 yes

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.997
_oxdiff_exptl_absorpt_empirical_full_min 0.386
####################################################################### 
# 
# 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_2b
_database_code_depnum_ccdc_archive 'CCDC 2076994'
loop_
_audit_author_name
_audit_author_address
'Barbara Modec'
;University of Ljubljana
Slovenia
;
_audit_update_record             
;
2022-02-17 deposited with the CCDC.	2022-03-18 downloaded from the CCDC.
;
_audit_creation_date             2022-02-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C11.5 H10.5 Cu0.5 N1.5 O2.5)'
_chemical_formula_sum            'C23 H21 Cu N3 O5'
_chemical_formula_weight         482.97
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   19.2147(5)
_cell_length_b                   7.9105(2)
_cell_length_c                   14.0321(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.901(3)
_cell_angle_gamma                90
_cell_volume                     2029.60(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5153
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      74.5110
_cell_measurement_theta_min      4.8230
_shelx_estimated_absorpt_T_max   0.833
_shelx_estimated_absorpt_T_min   0.704
_exptl_absorpt_coefficient_mu    1.890
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.12334
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.581
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             996
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0290
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11965
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.708
_diffrn_reflns_theta_min         4.837
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector_area_resol_mean 10.4933
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -48.00   35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5153   37.0000 -180.0000 83

#__ type_ start__ end____ width___ exp.time_
  2 omega  -53.00   -9.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5153  -77.0000 -150.0000 44

#__ type_ start__ end____ width___ exp.time_
  3 omega -119.00  -77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.5153  -77.0000 -150.0000 42

#__ type_ start__ end____ width___ exp.time_
  4 omega   15.00   50.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5153   37.0000 -180.0000 35

#__ type_ start__ end____ width___ exp.time_
  5 omega   13.00   60.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5153   57.0000 -120.0000 47

#__ type_ start__ end____ width___ exp.time_
  6 omega   55.00  126.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       40.5153 -178.0000  -30.0000 71

#__ type_ start__ end____ width___ exp.time_
  7 omega -133.00  -73.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  -90.0000 60

#__ type_ start__ end____ width___ exp.time_
  8 omega  -58.00  -29.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000 -120.0000 29

#__ type_ start__ end____ width___ exp.time_
  9 omega  -70.00  -29.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  150.0000 41

#__ type_ start__ end____ width___ exp.time_
 10 omega  -61.00  -28.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000 -180.0000 33

#__ type_ start__ end____ width___ exp.time_
 11 omega  -56.00  -31.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 12 omega  -53.00  -28.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 13 omega   81.00  173.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   61.0000 -180.0000 92

#__ type_ start__ end____ width___ exp.time_
 14 omega  103.00  129.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 15 omega   80.00  105.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   61.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 16 omega  142.00  173.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   61.0000  -90.0000 31

#__ type_ start__ end____ width___ exp.time_
 17 omega   76.00  101.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -94.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
 18 omega  146.00  172.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   15.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 19 omega   76.00  102.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 20 omega   81.00  131.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   61.0000  -90.0000 50

#__ type_ start__ end____ width___ exp.time_
 21 omega   78.00  104.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 22 omega   31.00   63.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -77.0000  150.0000 32

#__ type_ start__ end____ width___ exp.time_
 23 omega   73.00  142.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -77.0000  150.0000 69

#__ type_ start__ end____ width___ exp.time_
 24 omega   76.00  101.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 25 omega  136.00  165.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  111.0000 -180.0000 29

#__ type_ start__ end____ width___ exp.time_
 26 omega   76.00  102.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 27 omega   85.00  111.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   61.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
 28 omega   26.00   51.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -94.0000   90.0000 25

#__ type_ start__ end____ width___ exp.time_
 29 omega   32.00   90.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -30.0000  120.0000 58

#__ type_ start__ end____ width___ exp.time_
 30 omega   47.00   74.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -77.0000   30.0000 27

#__ type_ start__ end____ width___ exp.time_
 31 omega   48.00   98.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -45.0000   60.0000 50

#__ type_ start__ end____ width___ exp.time_
 32 omega   81.00  116.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000   90.0000 35

#__ type_ start__ end____ width___ exp.time_
 33 omega   80.00  107.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   61.0000  120.0000 27

#__ type_ start__ end____ width___ exp.time_
 34 omega   88.00  177.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   45.0000  150.0000 89

#__ type_ start__ end____ width___ exp.time_
 35 omega   81.00  107.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   61.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 36 omega  129.00  157.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000   90.0000 28

#__ type_ start__ end____ width___ exp.time_
 37 omega   44.00   90.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -94.0000 -150.0000 46

#__ type_ start__ end____ width___ exp.time_
 38 omega   94.00  178.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   45.0000   60.0000 84

#__ type_ start__ end____ width___ exp.time_
 39 omega   82.00  150.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   45.0000 -180.0000 68

#__ type_ start__ end____ width___ exp.time_
 40 omega   71.00  109.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000 -111.0000  -30.0000 38

#__ type_ start__ end____ width___ exp.time_
 41 omega  118.00  169.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   45.0000  120.0000 51

#__ type_ start__ end____ width___ exp.time_
 42 omega   76.00  102.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 43 omega   53.00   81.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -30.0000  -60.0000 28

#__ type_ start__ end____ width___ exp.time_
 44 omega   40.00   65.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -94.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
 45 omega   84.00  109.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   45.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 46 omega   84.00  110.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   45.0000 -120.0000 26

#__ type_ start__ end____ width___ exp.time_
 47 omega   86.00  111.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   45.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
 48 omega   79.00  106.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   61.0000  -60.0000 27

#__ type_ start__ end____ width___ exp.time_
 49 omega   76.00  122.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   77.0000 -150.0000 46

#__ type_ start__ end____ width___ exp.time_
 50 omega   78.00  104.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000   15.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 51 omega   70.00   95.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      109.5000  -45.0000  120.0000 25
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0024800000
_diffrn_orient_matrix_UB_12      0.0180359000
_diffrn_orient_matrix_UB_13      -0.1082165000
_diffrn_orient_matrix_UB_21      0.0841760000
_diffrn_orient_matrix_UB_22      0.0048967000
_diffrn_orient_matrix_UB_23      0.0389206000
_diffrn_orient_matrix_UB_31      0.0023486000
_diffrn_orient_matrix_UB_32      -0.1938936000
_diffrn_orient_matrix_UB_33      -0.0090600000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1874
_reflns_number_total             2071
_reflns_odcompleteness_completeness 98.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     75.12
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2071
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0341
_refine_ls_R_factor_gt           0.0307
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0445P)²+1.7652P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0826
_refine_ls_wR_factor_ref         0.0852
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2-H2A
 0.865 with sigma of 0.02
 C21-H2A \\sim H2A-C23
 with sigma of 0.02
3. Rigid bond restraints
 O2, N2, C21, C22, C23
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
4. Others
 Fixed Sof: H2A(0.5) Cu1(0.5) O2(0.5) H2(0.5) N2(0.5) C21(0.5) H21A(0.5)
 H21B(0.5) C22(0.5) H22A(0.5) H22B(0.5) C23(0.5) H23A(0.5) H23B(0.5) H23C(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C22(H22A,H22B)
5.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17)
5.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O1 O 1.04995(6) 0.42715(14) 0.14886(9) 0.0328(3) Uani 1 1 d . . . . .
O11 O 1.05785(6) 0.30575(17) 0.01044(8) 0.0331(3) Uani 1 1 d . . . . .
N1 N 0.92554(6) 0.26491(15) 0.13596(9) 0.0208(3) Uani 1 1 d . . . . .
C10 C 0.85937(7) 0.18939(19) 0.12783(11) 0.0227(3) Uani 1 1 d . . . . .
C11 C 0.82528(8) 0.2184(2) 0.20241(12) 0.0296(3) Uani 1 1 d . . . . .
H11 H 0.847450 0.288300 0.256500 0.036 Uiso 1 1 calc R . . . .
C12 C 0.75946(8) 0.1432(2) 0.19493(13) 0.0351(4) Uani 1 1 d . . . . .
H12 H 0.737648 0.162013 0.244677 0.042 Uiso 1 1 calc R . . . .
C13 C 0.72430(8) 0.0380(2) 0.11331(14) 0.0365(4) Uani 1 1 d . . . . .
H13 H 0.679597 -0.011489 0.109354 0.044 Uiso 1 1 calc R . . . .
C14 C 0.75578(9) 0.0089(2) 0.04032(13) 0.0343(4) Uani 1 1 d . . . . .
H14 H 0.732266 -0.060539 -0.013435 0.041 Uiso 1 1 calc R . . . .
C15 C 0.82425(8) 0.0832(2) 0.04508(11) 0.0270(3) Uani 1 1 d . . . . .
C16 C 0.85923(9) 0.0556(2) -0.02782(12) 0.0332(4) Uani 1 1 d . . . . .
H16 H 0.838045 -0.014973 -0.082007 0.040 Uiso 1 1 calc R . . . .
C17 C 0.92448(9) 0.1327(2) -0.01889(11) 0.0297(3) Uani 1 1 d . . . . .
H17 H 0.948163 0.115547 -0.066777 0.036 Uiso 1 1 calc R . . . .
C18 C 0.95531(8) 0.23850(19) 0.06384(10) 0.0226(3) Uani 1 1 d . . . . .
C19 C 1.02669(8) 0.33038(19) 0.07352(11) 0.0235(3) Uani 1 1 d . . . . .
H2A H 0.9690(12) 0.649(5) 0.1459(15) 0.027(9) Uiso 0.5 1 d D . P A -1
Cu1 Cu 0.98841(4) 0.43329(5) 0.23534(6) 0.0189(2) Uani 0.5 1 d . . P B -1
O2 O 1.11323(12) 0.6331(3) 0.3516(2) 0.0252(5) Uani 0.5 1 d . U P B -1
H2 H 1.100(2) 0.662(5) 0.401(3) 0.035(11) Uiso 0.5 1 d . . P C -1
N2 N 0.96708(12) 0.6602(3) 0.20523(17) 0.0208(5) Uani 0.5 1 d D U P B -1
C21 C 1.0122(2) 0.8059(4) 0.2536(8) 0.0255(11) Uani 0.5 1 d D U P B -1
H21A H 1.001087 0.835096 0.314410 0.031 Uiso 0.5 1 calc R . P B -1
H21B H 1.000560 0.902606 0.208981 0.031 Uiso 0.5 1 calc R . P B -1
C22 C 1.09347(19) 0.7653(5) 0.2788(3) 0.0241(7) Uani 0.5 1 d . U P B -1
H22A H 1.104265 0.730569 0.218523 0.029 Uiso 0.5 1 calc R . P B -1
H22B H 1.122018 0.865617 0.304721 0.029 Uiso 0.5 1 calc R . P B -1
C23 C 0.89056(19) 0.6847(6) 0.2019(4) 0.0305(8) Uani 0.5 1 d D U P B -1
H23A H 0.887699 0.690774 0.268898 0.046 Uiso 0.5 1 calc GR . P B -1
H23B H 0.861644 0.591470 0.167406 0.046 Uiso 0.5 1 calc GR . P B -1
H23C H 0.872358 0.787910 0.167135 0.046 Uiso 0.5 1 calc GR . P B -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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C19 1.2700(19) . ?
O1 Cu1 1.9379(15) . ?
O11 C19 1.2270(18) . ?
N1 C10 1.3774(18) . ?
N1 C18 1.3232(19) . ?
N1 Cu1 2.0353(13) . ?
C10 C11 1.414(2) . ?
C10 C15 1.424(2) . ?
C11 C12 1.372(2) . ?
C12 C13 1.409(3) . ?
C13 C14 1.360(3) . ?
C14 C15 1.424(2) . ?
C15 C16 1.403(2) . ?
C16 C17 1.365(2) . ?
C17 C18 1.406(2) . ?
C18 C19 1.521(2) . ?
Cu1 N2 1.861(2) . ?
O2 C22 1.429(4) . ?
N2 C21 1.476(5) . ?
N2 C23 1.469(4) . ?
C21 C22 1.525(5) . ?

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
C19 O1 Cu1 114.21(9) . . ?
C10 N1 Cu1 132.76(11) . . ?
C18 N1 C10 118.24(13) . . ?
C18 N1 Cu1 108.80(10) . . ?
N1 C10 C11 119.63(13) . . ?
N1 C10 C15 121.16(14) . . ?
C11 C10 C15 119.21(13) . . ?
C12 C11 C10 119.94(15) . . ?
C11 C12 C13 121.23(16) . . ?
C14 C13 C12 119.96(15) . . ?
C13 C14 C15 120.88(16) . . ?
C14 C15 C10 118.77(15) . . ?
C16 C15 C10 118.24(14) . . ?
C16 C15 C14 122.98(15) . . ?
C17 C16 C15 119.72(14) . . ?
C16 C17 C18 118.94(14) . . ?
N1 C18 C17 123.65(14) . . ?
N1 C18 C19 116.50(13) . . ?
C17 C18 C19 119.85(13) . . ?
O1 C19 C18 116.06(12) . . ?
O11 C19 O1 124.84(14) . . ?
O11 C19 C18 119.09(14) . . ?
O1 Cu1 N1 84.40(6) . . ?
N2 Cu1 O1 90.93(9) . . ?
N2 Cu1 N1 115.65(8) . . ?
C21 N2 Cu1 126.3(3) . . ?
C23 N2 Cu1 106.4(2) . . ?
C23 N2 C21 110.7(4) . . ?
N2 C21 C22 110.9(3) . . ?
O2 C22 C21 110.4(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
_geom_hbond_publ_flag
N2 H2A O11 0.849(19) 2.12(2) 2.927(3) 158(3) 5_765 yes
O2 H2 O11 0.85(5) 1.95(5) 2.792(3) 170(4) 6_566 yes

####################################################################### 
# 
# 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_8e
_database_code_depnum_ccdc_archive 'CCDC 2077004'
loop_
_audit_author_name
_audit_author_address
'Barbara Modec'
;University of Ljubljana
Slovenia
;
_audit_update_record             
;
2022-02-17 deposited with the CCDC.	2022-03-18 downloaded from the CCDC.
;
_audit_creation_date             2022-02-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H27 Cu N3 O3, 2(C10 H6 N O2)'
_chemical_formula_sum            'C29 H39 Cu N5 O7'
_chemical_formula_weight         633.19
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   11.0057(3)
_cell_length_b                   11.4891(4)
_cell_length_c                   12.6324(4)
_cell_angle_alpha                81.107(3)
_cell_angle_beta                 79.836(3)
_cell_angle_gamma                73.162(3)
_cell_volume                     1495.73(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    10431
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      29.3040
_cell_measurement_theta_min      3.4610
_shelx_estimated_absorpt_T_max   0.940
_shelx_estimated_absorpt_T_min   0.744
_exptl_absorpt_coefficient_mu    0.784
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             666
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            26975
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.858
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.258
_diffrn_reflns_theta_min         2.348
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -12.00  78.00   1.00   25.00    --   14.05  37.00 -90.00   90
  2  ω    -24.00  48.00   1.00   25.00    --   14.05 -77.00 -90.00   72
  3  ω    -16.00  88.00   1.00   25.00    --   14.05  57.00 150.00  104
  4  ω     -2.00  56.00   1.00   25.00    --   14.05 -99.00-120.00   58
  5  ω    -62.00  26.00   1.00   25.00    --   14.05 -37.00  90.00   88
  6  ω    -22.00  74.00   1.00   25.00    --   14.05  19.00  90.00   96
  7  ω    -86.00 -59.00   1.00   25.00    --  -14.36 147.00  46.05   27
  8  ω    -48.00  21.00   1.00   25.00    --  -14.36  77.00   0.00   69
  9  ω    -33.00  19.00   1.00   25.00    --  -14.36 -77.00-120.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0197009000
_diffrn_orient_matrix_UB_12      0.0527746000
_diffrn_orient_matrix_UB_13      0.0031969000
_diffrn_orient_matrix_UB_21      0.0118910000
_diffrn_orient_matrix_UB_22      -0.0218615000
_diffrn_orient_matrix_UB_23      0.0538857000
_diffrn_orient_matrix_UB_31      0.0639862000
_diffrn_orient_matrix_UB_32      -0.0307936000
_diffrn_orient_matrix_UB_33      -0.0194923000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.891
_reflns_Friedel_fraction_full    0.994
_reflns_Friedel_fraction_max     0.808
_reflns_number_gt                13229
_reflns_number_total             15312
_reflns_odcompleteness_completeness 99.93
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.425
_refine_diff_density_min         -0.713
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 
;
 Flack x determined using 5427 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.012(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1042
_refine_ls_number_reflns         15312
_refine_ls_number_restraints     584
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0440
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0466P)²+0.5613P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0990
_refine_ls_wR_factor_ref         0.1079
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O5-H5
 0.85 with sigma of 0.01
 O5A-H5AA
 0.85 with sigma of 0.01
 O4-H4
 0.85 with sigma of 0.01
 O4A-H4AA
 0.85 with sigma of 0.01
 O3-H3
 0.85 with sigma of 0.01
 Cu2-H5AA
 2.656161 with sigma of 0.02
 Cu2-H5
 2.823847 with sigma of 0.02
 Cu2-H4
 3.162576 with sigma of 0.02
 C52A-H5AA
 1.894643 with sigma of 0.02
 Cu2-H4AA
 3.054282 with sigma of 0.02
 C52-H5
 1.909403 with sigma of 0.02
 C42-H4
 1.8928 with sigma of 0.02
 C42A-H4AA
 1.90519 with sigma of 0.02
 O9-C99 \\sim O9A-C99A
 with sigma of 0.02
 C96-C98 \\sim C96A-C98A
 with sigma of 0.04
 C90-C98 \\sim C90A-C98A
 with sigma of 0.04
 N9-C91 \\sim N9A-C91A
 with sigma of 0.04
 O99-C99 \\sim O99A-C99A
 with sigma of 0.02
 N9-C90 \\sim N9A-C90A
 with sigma of 0.02
 N9-C98 \\sim N9A-C98A
 with sigma of 0.02
 C90-C91 \\sim C90A-C91A
 with sigma of 0.02
 N9-C97 \\sim N9A-C97A
 with sigma of 0.04
 C90-C95 \\sim C90A-C95A
 with sigma of 0.02
 C90-C94 \\sim C90A-C94A
 with sigma of 0.04
 C91-C93 \\sim C91A-C93A
 with sigma of 0.04
 C91-C92 \\sim C91A-C92A
 with sigma of 0.02
 C92-C94 \\sim C92A-C94A
 with sigma of 0.04
 C92-C93 \\sim C92A-C93A
 with sigma of 0.02
 C95-C97 \\sim C95A-C97A
 with sigma of 0.04
 C97-C99 \\sim C97A-C99A
 with sigma of 0.04
 C93-C94 \\sim C93A-C94A
 with sigma of 0.02
 C94-C95 \\sim C94A-C95A
 with sigma of 0.02
 C95-C96 \\sim C95A-C96A
 with sigma of 0.02
 N9-C95 \\sim N9A-C95A
 with sigma of 0.04
 N9-C99 \\sim N9A-C99A
 with sigma of 0.04
 C96-C97 \\sim C96A-C97A
 with sigma of 0.02
 C90-C92 \\sim C90A-C92A
 with sigma of 0.04
 C90-C96 \\sim C90A-C96A
 with sigma of 0.04
 C97-C98 \\sim C97A-C98A
 with sigma of 0.02
 C98-C99 \\sim C98A-C99A
 with sigma of 0.02
 C91-C95 \\sim C91A-C95A
 with sigma of 0.04
 C93-C95 \\sim C93A-C95A
 with sigma of 0.04
 C94-C96 \\sim C94A-C96A
 with sigma of 0.04
 O9-O99 \\sim O9A-O99A
 with sigma of 0.04
 O9-C98 \\sim O9A-C98A
 with sigma of 0.04
 O99-C98 \\sim O99A-C98A
 with sigma of 0.04
 Cu2-N5 \\sim Cu2-N5A
 with sigma of 0.02
 O5-C52 \\sim O5A-C52A
 with sigma of 0.02
 Cu2-O5 \\sim Cu2-O5A
 with sigma of 0.02
 N5-C51 \\sim N5A-C51A
 with sigma of 0.02
 C51-C52 \\sim C51A-C52A
 with sigma of 0.02
 C51-C53 \\sim C51A-C53A
 with sigma of 0.02
 C52-C53 \\sim C52A-C53A
 with sigma of 0.04
 Cu2-C51 \\sim Cu2-C51A
 with sigma of 0.04
 Cu2-C52 \\sim Cu2-C52A
 with sigma of 0.04
 O5-C51 \\sim O5A-C51A
 with sigma of 0.04
 N5-C52 \\sim N5A-C52A
 with sigma of 0.04
 N5-C53 \\sim N5A-C53A
 with sigma of 0.04
 Cu2-O6A \\sim Cu2-O6
 with sigma of 0.02
 O6A-C62A \\sim O6-C62
 with sigma of 0.02
 C62A-C61A \\sim C62-C61
 with sigma of 0.02
 C63A-C61A \\sim C63-C61
 with sigma of 0.02
 Cu2-O4A \\sim Cu2-O4
 with sigma of 0.02
 Cu2-N4 \\sim Cu2-N4A
 with sigma of 0.02
 O4-C42 \\sim O4A-C42A
 with sigma of 0.02
 N4-C41 \\sim N4A-C41A
 with sigma of 0.02
 C43-C41 \\sim C43A-C41A
 with sigma of 0.02
 C42A-C41A \\sim C42-C41
 with sigma of 0.02
 N6A-C61A \\sim N6-C61
 with sigma of 0.02
 Cu2-N6A \\sim Cu2-N6
 with sigma of 0.02
3. Restrained planarity
 N9A, C90A, C91A, C92A, C93A, C94A, C95A, C96A, C97A, C98A
 with sigma of 0.001
4. Uiso/Uaniso restraints and constraints
Uanis(C95) \\sim Ueq, Uanis(C95A) \\sim Ueq, Uanis(C90) \\sim Ueq, Uanis(C90A)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 O9A, O99A, N9A, C90A, C91A, C92A, C93A, C94A, C95A, C96A, C97A, C98A, C99A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 O9, O99, N9, C90, C91, C92, C93, C94, C95, C96, C97, C98, C99
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 Cu2, O4, O5, O6, N4, N5, N6, C41, C42, C43, C51, C52, C53, C61, C62, C63, O4A,
  O5A, O6A, N4A, N5A, N6A, C41A, C42A, C43A, C51A, C52A, C53A, C61A, C62A, C63A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
6. Others
 Sof(O9A)=Sof(O99A)=Sof(N9A)=Sof(C90A)=Sof(C91A)=Sof(H91A)=Sof(C92A)=Sof(H92A)=
 Sof(C93A)=Sof(H93A)=Sof(C94A)=Sof(H94A)=Sof(C95A)=Sof(C96A)=Sof(H96A)=
 Sof(C97A)=Sof(H97A)=Sof(C98A)=Sof(C99A)=1-FVAR(1)
 Sof(O9)=Sof(O99)=Sof(N9)=Sof(C90)=Sof(C91)=Sof(H91)=Sof(C92)=Sof(H92)=
 Sof(C93)=Sof(H93)=Sof(C94)=Sof(H94)=Sof(C95)=Sof(C96)=Sof(H96)=Sof(C97)=
 Sof(H97)=Sof(C98)=Sof(C99)=FVAR(1)
 Fixed Sof: O4(0.5) H4(0.5) O5(0.5) H5(0.5) O6(0.5) H6(0.5) N4(0.5) H4A(0.5)
 H4B(0.5) N5(0.5) H5A(0.5) H5B(0.5) N6(0.5) H6A(0.5) H6B(0.5) C41(0.5) H41(0.5)
 C42(0.5) H42A(0.5) H42B(0.5) C43(0.5) H43A(0.5) H43B(0.5) H43C(0.5) C51(0.5)
 H51(0.5) C52(0.5) H52A(0.5) H52B(0.5) C53(0.5) H53A(0.5) H53B(0.5) H53C(0.5)
 C61(0.5) H61(0.5) C62(0.5) H62A(0.5) H62B(0.5) C63(0.5) H63A(0.5) H63B(0.5)
 H63C(0.5) O4A(0.5) H4AA(0.5) O5A(0.5) H5AA(0.5) O6A(0.5) H6AA(0.5) N4A(0.5)
 H4AB(0.5) H4AC(0.5) N5A(0.5) H5AB(0.5) H5AC(0.5) N6A(0.5) H6AB(0.5) H6AC(0.5)
 C41A(0.5) H41A(0.5) C42A(0.5) H42C(0.5) H42D(0.5) C43A(0.5) H43D(0.5)
 H43E(0.5) H43F(0.5) C51A(0.5) H51A(0.5) C52A(0.5) H52C(0.5) H52D(0.5)
 C53A(0.5) H53D(0.5) H53E(0.5) H53F(0.5) C61A(0.5) H61A(0.5) C62A(0.5)
 H62C(0.5) H62D(0.5) C63A(0.5) H63D(0.5) H63E(0.5) H63F(0.5)
7.a Ternary CH refined with riding coordinates:
 C11(H11), C21(H21), C31(H31), C41(H41), C51(H51), C61(H61), C41A(H41A),
 C51A(H51A), C61A(H61A)
7.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2A,H2B), N3(H3A,H3B), C12(H12A,H12B), C22(H22A,H22B),
 C32(H32A,H32B), N4(H4A,H4B), N5(H5A,H5B), N6(H6A,H6B), C42(H42A,H42B),
 C52(H52A,H52B), C62(H62A,H62B), N4A(H4AB,H4AC), N5A(H5AB,H5AC), N6A(H6AB,H6AC),
  C42A(H42C,H42D), C52A(H52C,H52D), C62A(H62C,H62D)
7.c Aromatic/amide H refined with riding coordinates:
 C71(H71), C72(H72), C73(H73), C74(H74), C76(H76), C77(H77), C81(H81),
 C82(H82), C83(H83), C84(H84), C86(H86), C87(H87), C101(H101), C102(H102),
 C103(H103), C104(H104), C106(H106), C107(H107), C91(H91), C92(H92), C93(H93),
 C94(H94), C96(H96), C97(H97), C91A(H91A), C92A(H92A), C93A(H93A), C94A(H94A),
 C96A(H96A), C97A(H97A)
7.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C23(H23A,H23B,H23C), C33(H33A,H33B,H33C), C43(H43A,H43B,
 H43C), C53(H53A,H53B,H53C), C63(H63A,H63B,H63C), C43A(H43D,H43E,H43F),
 C53A(H53D,H53E,H53F), C63A(H63D,H63E,H63F)
7.e Idealised tetrahedral OH refined as rotating group:
 O6(H6), O6A(H6AA)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.0966(9) 1.0927(7) 0.5374(6) 0.02605(12) Uani 1 1 d . . . . .
Cu2 Cu 0.4887(9) 0.5174(7) 0.4647(6) 0.04145(16) Uani 1 1 d D U . . .
O1 O 0.2691(9) 1.0149(8) 0.5905(7) 0.0370(7) Uani 1 1 d . . . . .
H1 H 0.282(6) 0.947(6) 0.618(5) 0.056 Uiso 1 1 d R . . . .
O2 O 0.1009(10) 0.8939(8) 0.4935(7) 0.0538(10) Uani 1 1 d . . . . .
H2 H 0.157(7) 0.877(7) 0.444(6) 0.081 Uiso 1 1 d R . . . .
O3 O 0.0479(10) 1.2926(8) 0.5872(7) 0.0729(15) Uani 1 1 d D . . . .
H3 H 0.021(8) 1.338(7) 0.533(4) 0.109 Uiso 1 1 d DR . . . .
O7 O 0.2829(10) 0.8575(8) 0.3239(7) 0.0698(15) Uani 1 1 d . . . . .
O8 O 0.3210(9) 0.7901(8) 0.6831(7) 0.0635(14) Uani 1 1 d . . . . .
O10 O 0.7147(10) 0.1871(8) 0.6323(7) 0.0646(15) Uani 1 1 d . . . . .
O77 O 0.3875(11) 0.7515(8) 0.1936(7) 0.093(2) Uani 1 1 d . . . . .
O88 O 0.1688(10) 0.8706(8) 0.8151(7) 0.0547(10) Uani 1 1 d . . . . .
O101 O 0.5278(10) 0.1728(8) 0.6037(8) 0.0646(13) Uani 1 1 d . . . . .
N1 N 0.2050(9) 1.1407(7) 0.4020(7) 0.0292(7) Uani 1 1 d . . . . .
H1A H 0.208016 1.094063 0.351010 0.035 Uiso 1 1 calc R . . . .
H1B H 0.171231 1.218320 0.377729 0.035 Uiso 1 1 calc R . . . .
N2 N -0.0647(9) 1.1348(8) 0.4653(7) 0.0404(9) Uani 1 1 d . . . . .
H2A H -0.132970 1.148936 0.515949 0.049 Uiso 1 1 calc R . . . .
H2B H -0.068474 1.203443 0.420758 0.049 Uiso 1 1 calc R . . . .
N3 N 0.0056(9) 1.0687(7) 0.6868(7) 0.0296(7) Uani 1 1 d . . . . .
H3A H -0.073776 1.066318 0.683540 0.036 Uiso 1 1 calc R . . . .
H3B H 0.046055 0.997500 0.720079 0.036 Uiso 1 1 calc R . . . .
N7 N 0.2024(10) 1.0579(8) 0.1770(7) 0.0397(10) Uani 1 1 d . . . . .
N8 N 0.3819(10) 0.5739(8) 0.8158(7) 0.0450(12) Uani 1 1 d . . . . .
N10 N 0.7546(9) -0.0383(8) 0.7512(7) 0.0325(9) Uani 1 1 d . . . . .
C11 C 0.3352(9) 1.1249(8) 0.4263(7) 0.0302(8) Uani 1 1 d . . . . .
H11 H 0.334547 1.193093 0.464547 0.036 Uiso 1 1 calc R . . . .
C12 C 0.3698(9) 1.0076(8) 0.4998(7) 0.0328(9) Uani 1 1 d . . . . .
H12A H 0.376988 0.938228 0.461800 0.039 Uiso 1 1 calc R . . . .
H12B H 0.451205 0.997837 0.524369 0.039 Uiso 1 1 calc R . . . .
C13 C 0.4342(10) 1.1205(8) 0.3245(7) 0.0437(11) Uani 1 1 d . . . . .
H13A H 0.434916 1.054386 0.286122 0.066 Uiso 1 1 calc GR . . . .
H13B H 0.517580 1.108121 0.344579 0.066 Uiso 1 1 calc GR . . . .
H13C H 0.412356 1.196354 0.278831 0.066 Uiso 1 1 calc GR . . . .
C21 C -0.0709(10) 1.0386(10) 0.4039(8) 0.0591(17) Uani 1 1 d . . . . .
H21 H -0.011968 1.040632 0.336135 0.071 Uiso 1 1 calc R . . . .
C22 C -0.0259(11) 0.9159(10) 0.4683(8) 0.065(2) Uani 1 1 d . . . . .
H22A H -0.084435 0.912087 0.535071 0.078 Uiso 1 1 calc R . . . .
H22B H -0.028177 0.851962 0.427343 0.078 Uiso 1 1 calc R . . . .
C23 C -0.2049(11) 1.0562(13) 0.3760(9) 0.112(4) Uani 1 1 d . . . . .
H23A H -0.205260 0.988694 0.339863 0.168 Uiso 1 1 calc GR . . . .
H23B H -0.228509 1.130972 0.329265 0.168 Uiso 1 1 calc GR . . . .
H23C H -0.265081 1.060042 0.441173 0.168 Uiso 1 1 calc GR . . . .
C31 C 0.0006(10) 1.1693(8) 0.7498(7) 0.0394(11) Uani 1 1 d . . . . .
H31 H 0.087795 1.160819 0.763479 0.047 Uiso 1 1 calc R . . . .
C32 C -0.0434(11) 1.2908(8) 0.6823(7) 0.0546(15) Uani 1 1 d . . . . .
H32A H -0.127417 1.299867 0.663030 0.065 Uiso 1 1 calc R . . . .
H32B H -0.048974 1.357609 0.723011 0.065 Uiso 1 1 calc R . . . .
C33 C -0.0838(10) 1.1641(9) 0.8583(7) 0.0495(12) Uani 1 1 d . . . . .
H33A H -0.169557 1.170369 0.847086 0.074 Uiso 1 1 calc GR . . . .
H33B H -0.084288 1.230682 0.896053 0.074 Uiso 1 1 calc GR . . . .
H33C H -0.050794 1.087926 0.900515 0.074 Uiso 1 1 calc GR . . . .
C70 C 0.1704(10) 1.1543(9) 0.1014(8) 0.0466(13) Uani 1 1 d . . . . .
C71 C 0.0908(12) 1.2666(9) 0.1353(8) 0.074(2) Uani 1 1 d . . . . .
H71 H 0.057420 1.272087 0.207848 0.089 Uiso 1 1 calc R . . . .
C72 C 0.0630(12) 1.3671(10) 0.0609(9) 0.089(3) Uani 1 1 d . . . . .
H72 H 0.010664 1.440505 0.084155 0.106 Uiso 1 1 calc R . . . .
C73 C 0.1098(12) 1.3629(10) -0.0472(9) 0.081(2) Uani 1 1 d . . . . .
H73 H 0.090278 1.433442 -0.095293 0.097 Uiso 1 1 calc R . . . .
C74 C 0.1851(11) 1.2559(9) -0.0844(8) 0.0579(15) Uani 1 1 d . . . . .
H74 H 0.215783 1.253181 -0.157713 0.070 Uiso 1 1 calc R . . . .
C75 C 0.2158(10) 1.1491(9) -0.0103(8) 0.0456(13) Uani 1 1 d . . . . .
C76 C 0.2930(11) 1.0355(9) -0.0426(8) 0.0528(14) Uani 1 1 d . . . . .
H76 H 0.322277 1.026356 -0.115333 0.063 Uiso 1 1 calc R . . . .
C77 C 0.3235(10) 0.9408(9) 0.0339(8) 0.0499(14) Uani 1 1 d . . . . .
H77 H 0.374540 0.865445 0.013722 0.060 Uiso 1 1 calc R . . . .
C78 C 0.2789(10) 0.9543(8) 0.1445(7) 0.0349(10) Uani 1 1 d . . . . .
C79 C 0.3181(10) 0.8460(8) 0.2297(7) 0.0372(11) Uani 1 1 d . . . . .
C80 C 0.4131(10) 0.4684(9) 0.8859(8) 0.0440(13) Uani 1 1 d . . . . .
C81 C 0.5006(10) 0.3626(9) 0.8458(8) 0.0536(15) Uani 1 1 d . . . . .
H81 H 0.538080 0.366266 0.773793 0.064 Uiso 1 1 calc R . . . .
C82 C 0.5305(10) 0.2562(9) 0.9109(8) 0.0529(15) Uani 1 1 d . . . . .
H82 H 0.587076 0.187009 0.883251 0.063 Uiso 1 1 calc R . . . .
C83 C 0.4755(11) 0.2501(9) 1.0214(8) 0.0571(17) Uani 1 1 d . . . . .
H83 H 0.496175 0.176949 1.066195 0.068 Uiso 1 1 calc R . . . .
C84 C 0.3928(11) 0.3509(9) 1.0615(8) 0.068(2) Uani 1 1 d . . . . .
H84 H 0.357497 0.346276 1.134033 0.082 Uiso 1 1 calc R . . . .
C85 C 0.3594(11) 0.4625(9) 0.9956(8) 0.0577(18) Uani 1 1 d . . . . .
C86 C 0.2711(11) 0.5673(9) 1.0317(8) 0.078(3) Uani 1 1 d . . . . .
H86 H 0.233691 0.566491 1.103758 0.094 Uiso 1 1 calc R . . . .
C87 C 0.2391(11) 0.6716(9) 0.9621(8) 0.064(2) Uani 1 1 d . . . . .
H87 H 0.180244 0.741883 0.985807 0.077 Uiso 1 1 calc R . . . .
C88 C 0.2974(10) 0.6697(9) 0.8538(8) 0.0456(14) Uani 1 1 d . . . . .
C89 C 0.2588(10) 0.7867(9) 0.7775(8) 0.0488(16) Uani 1 1 d . . . . .
C100 C 0.7698(9) -0.1500(8) 0.8131(7) 0.0336(10) Uani 1 1 d . . . . .
C101 C 0.8854(10) -0.2038(8) 0.8571(8) 0.0451(13) Uani 1 1 d . . . . .
H101 H 0.950348 -0.164455 0.843548 0.054 Uiso 1 1 calc R . . . .
C102 C 0.9014(11) -0.3132(9) 0.9192(8) 0.0570(16) Uani 1 1 d . . . . .
H102 H 0.976826 -0.347178 0.949324 0.068 Uiso 1 1 calc R . . . .
C103 C 0.8069(11) -0.3758(9) 0.9388(8) 0.0632(18) Uani 1 1 d . . . . .
H103 H 0.821177 -0.451848 0.979728 0.076 Uiso 1 1 calc R . . . .
C104 C 0.6945(11) -0.3265(9) 0.8985(8) 0.0546(15) Uani 1 1 d . . . . .
H104 H 0.631941 -0.368707 0.912288 0.066 Uiso 1 1 calc R . . . .
C105 C 0.6719(10) -0.2110(9) 0.8356(7) 0.0402(11) Uani 1 1 d . . . . .
C106 C 0.5574(10) -0.1549(9) 0.7928(8) 0.0435(13) Uani 1 1 d . . . . .
H106 H 0.491818 -0.193458 0.805409 0.052 Uiso 1 1 calc R . . . .
C107 C 0.5421(10) -0.0443(9) 0.7328(7) 0.0401(12) Uani 1 1 d . . . . .
H107 H 0.465828 -0.005546 0.705018 0.048 Uiso 1 1 calc R . . . .
C108 C 0.6446(10) 0.0109(8) 0.7134(7) 0.0323(10) Uani 1 1 d . . . . .
C109 C 0.6287(10) 0.1347(9) 0.6444(7) 0.0419(12) Uani 1 1 d . . . . .
O4 O 0.5734(10) 0.5241(9) 0.6254(8) 0.0336(12) Uani 0.5 1 d D U P A 1
H4 H 0.554(7) 0.521(8) 0.6946(13) 0.050 Uiso 0.5 1 d DR . P B 1
O5 O 0.3947(15) 0.3851(12) 0.5299(18) 0.045(2) Uani 0.5 1 d D U P A 1
H5 H 0.401(8) 0.310(4) 0.526(8) 0.067 Uiso 0.5 1 d DR . P C 1
O6 O 0.4500(10) 0.5297(9) 0.2829(8) 0.0315(11) Uani 0.5 1 d D U P A 1
H6 H 0.419624 0.599949 0.256769 0.047 Uiso 0.5 1 calc GR . P A 1
O9 O 0.9016(11) 0.4314(10) 0.4096(9) 0.039(2) Uani 0.547(11) 1 d D U P D 1
O99 O 1.1065(10) 0.4079(9) 0.3386(8) 0.047(2) Uani 0.547(11) 1 d D U P D 1
N4 N 0.5843(19) 0.6531(16) 0.4170(11) 0.0306(19) Uani 0.5 1 d D U P A 1
H4A H 0.659558 0.621752 0.378445 0.037 Uiso 0.5 1 calc R . P A 1
H4B H 0.538581 0.712787 0.374560 0.037 Uiso 0.5 1 calc R . P A 1
N5 N 0.3242(12) 0.6203(11) 0.5578(11) 0.052(2) Uani 0.5 1 d D U P A 1
H5A H 0.344588 0.630268 0.620333 0.062 Uiso 0.5 1 calc R . P A 1
H5B H 0.296080 0.693912 0.522376 0.062 Uiso 0.5 1 calc R . P A 1
N6 N 0.6593(11) 0.3934(10) 0.3968(9) 0.0332(14) Uani 0.5 1 d D U P A 1
H6A H 0.725349 0.424633 0.392741 0.040 Uiso 0.5 1 calc R . P A 1
H6B H 0.674358 0.323185 0.439769 0.040 Uiso 0.5 1 calc R . P A 1
N9 N 0.8481(13) 0.6336(14) 0.2506(12) 0.0245(17) Uani 0.547(11) 1 d D U P D 1
C41 C 0.6061(13) 0.7057(12) 0.5112(10) 0.0282(19) Uani 0.5 1 d D U P A 1
H41 H 0.522118 0.752290 0.544134 0.034 Uiso 0.5 1 calc R . P A 1
C42 C 0.6564(14) 0.6022(12) 0.5930(11) 0.0354(19) Uani 0.5 1 d D U P A 1
H42A H 0.740012 0.554553 0.562785 0.042 Uiso 0.5 1 calc R . P A 1
H42B H 0.667004 0.634897 0.656076 0.042 Uiso 0.5 1 calc R . P A 1
C43 C 0.6896(14) 0.7941(12) 0.4781(11) 0.044(2) Uani 0.5 1 d D U P A 1
H43A H 0.776174 0.749270 0.455090 0.065 Uiso 0.5 1 calc GR . P A 1
H43B H 0.687727 0.836022 0.538721 0.065 Uiso 0.5 1 calc GR . P A 1
H43C H 0.657514 0.852570 0.419729 0.065 Uiso 0.5 1 calc GR . P A 1
C51 C 0.2208(14) 0.5553(13) 0.5791(14) 0.054(3) Uani 0.5 1 d D U P A 1
H51 H 0.188161 0.557981 0.511171 0.065 Uiso 0.5 1 calc R . P A 1
C52 C 0.291(2) 0.4265(16) 0.6132(18) 0.048(4) Uani 0.5 1 d D U P A 1
H52A H 0.323303 0.422287 0.680550 0.058 Uiso 0.5 1 calc R . P A 1
H52B H 0.232807 0.374610 0.624682 0.058 Uiso 0.5 1 calc R . P A 1
C53 C 0.1088(15) 0.6103(16) 0.6634(16) 0.072(4) Uani 0.5 1 d D U P A 1
H53A H 0.140266 0.609034 0.729944 0.109 Uiso 0.5 1 calc GR . P A 1
H53B H 0.047559 0.563064 0.675816 0.109 Uiso 0.5 1 calc GR . P A 1
H53C H 0.068489 0.693143 0.637446 0.109 Uiso 0.5 1 calc GR . P A 1
C61 C 0.6479(12) 0.3688(11) 0.2838(10) 0.0349(16) Uani 0.5 1 d D U P A 1
H61 H 0.602593 0.305253 0.292283 0.042 Uiso 0.5 1 calc R . P A 1
C62 C 0.5693(13) 0.4824(13) 0.2262(11) 0.038(2) Uani 0.5 1 d D U P A 1
H62A H 0.615968 0.544268 0.212551 0.046 Uiso 0.5 1 calc R . P A 1
H62B H 0.558229 0.463929 0.156674 0.046 Uiso 0.5 1 calc R . P A 1
C63 C 0.7746(13) 0.3249(12) 0.2163(11) 0.056(3) Uani 0.5 1 d D U P A 1
H63A H 0.761413 0.307619 0.147888 0.084 Uiso 0.5 1 calc GR . P A 1
H63B H 0.824313 0.251898 0.253017 0.084 Uiso 0.5 1 calc GR . P A 1
H63C H 0.819502 0.387047 0.204646 0.084 Uiso 0.5 1 calc GR . P A 1
C90 C 0.8224(17) 0.7461(14) 0.1902(13) 0.0259(16) Uani 0.547(11) 1 d D U P D 1
C91 C 0.7015(17) 0.7915(14) 0.1515(13) 0.029(2) Uani 0.547(11) 1 d D U P D 1
H91 H 0.643494 0.744290 0.165381 0.035 Uiso 0.547(11) 1 calc R . P D 1
C92 C 0.6708(18) 0.9046(14) 0.0938(15) 0.033(2) Uani 0.547(11) 1 d D U P D 1
H92 H 0.590850 0.933708 0.070448 0.039 Uiso 0.547(11) 1 calc R . P D 1
C93 C 0.7550(18) 0.9771(17) 0.0692(16) 0.036(3) Uani 0.547(11) 1 d D U P D 1
H93 H 0.731568 1.053593 0.029857 0.044 Uiso 0.547(11) 1 calc R . P D 1
C94 C 0.8731(19) 0.9356(17) 0.1032(16) 0.043(3) Uani 0.547(11) 1 d D U P D 1
H94 H 0.930884 0.983031 0.084639 0.051 Uiso 0.547(11) 1 calc R . P D 1
C95 C 0.9084(17) 0.8198(15) 0.1669(14) 0.031(2) Uani 0.547(11) 1 d D U P D 1
C96 C 1.0276(17) 0.7712(15) 0.2050(15) 0.039(3) Uani 0.547(11) 1 d D U P D 1
H96 H 1.087548 0.816305 0.191850 0.046 Uiso 0.547(11) 1 calc R . P D 1
C97 C 1.0551(16) 0.6566(14) 0.2616(13) 0.031(2) Uani 0.547(11) 1 d D U P D 1
H97 H 1.134253 0.623056 0.285882 0.038 Uiso 0.547(11) 1 calc R . P D 1
C98 C 0.9623(13) 0.5908(12) 0.2823(13) 0.0234(18) Uani 0.547(11) 1 d D U P D 1
C99 C 0.9913(13) 0.4663(11) 0.3503(11) 0.0276(19) Uani 0.547(11) 1 d D U P D 1
O4A O 0.6101(12) 0.4575(11) 0.6039(9) 0.0561(18) Uani 0.5 1 d D U P A 2
H4AA H 0.608(8) 0.421(8) 0.669(4) 0.084 Uiso 0.5 1 d DR . P E 2
O5A O 0.4221(16) 0.3732(13) 0.5251(19) 0.048(2) Uani 0.5 1 d D U P A 2
H5AA H 0.459(4) 0.302(3) 0.554(6) 0.073 Uiso 0.5 1 d DR . P F 2
O6A O 0.3635(13) 0.5644(11) 0.3344(9) 0.069(2) Uani 0.5 1 d D U P A 2
H6AA H 0.397198 0.617008 0.301628 0.104 Uiso 0.5 1 calc GR . P A 2
O9A O 0.8702(12) 0.4031(11) 0.3614(11) 0.045(2) Uani 0.453(11) 1 d D U P D 2
O99A O 1.0483(13) 0.4216(12) 0.4090(10) 0.058(3) Uani 0.453(11) 1 d D U P D 2
N4A N 0.574(2) 0.6562(16) 0.4427(12) 0.041(2) Uani 0.5 1 d D U P A 2
H4AB H 0.639431 0.643446 0.389258 0.049 Uiso 0.5 1 calc R . P A 2
H4AC H 0.518150 0.726778 0.424763 0.049 Uiso 0.5 1 calc R . P A 2
N5A N 0.3221(12) 0.6196(10) 0.5054(8) 0.0298(14) Uani 0.5 1 d D U P A 2
H5AB H 0.321489 0.656460 0.562601 0.036 Uiso 0.5 1 calc R . P A 2
H5AC H 0.298420 0.676699 0.451265 0.036 Uiso 0.5 1 calc R . P A 2
N6A N 0.6029(14) 0.4001(11) 0.3765(10) 0.0520(18) Uani 0.5 1 d D U P A 2
H6AB H 0.679902 0.413983 0.364215 0.062 Uiso 0.5 1 calc R . P A 2
H6AC H 0.610757 0.325628 0.411922 0.062 Uiso 0.5 1 calc R . P A 2
N9A N 0.8187(14) 0.6434(8) 0.2682(5) 0.027(2) Uani 0.453(11) 1 d D U P D 2
C41A C 0.6218(15) 0.6622(15) 0.5456(13) 0.047(2) Uani 0.5 1 d D U P A 2
H41A H 0.547003 0.694678 0.597935 0.056 Uiso 0.5 1 calc R . P A 2
C42A C 0.6875(15) 0.5391(14) 0.5912(11) 0.049(2) Uani 0.5 1 d D U P A 2
H42C H 0.766236 0.507851 0.543921 0.059 Uiso 0.5 1 calc R . P A 2
H42D H 0.709892 0.543815 0.661048 0.059 Uiso 0.5 1 calc R . P A 2
C43A C 0.7061(16) 0.7487(15) 0.5274(14) 0.059(3) Uani 0.5 1 d D U P A 2
H43D H 0.733750 0.752409 0.594509 0.089 Uiso 0.5 1 calc GR . P A 2
H43E H 0.658498 0.828810 0.500923 0.089 Uiso 0.5 1 calc GR . P A 2
H43F H 0.779623 0.719710 0.475377 0.089 Uiso 0.5 1 calc GR . P A 2
C51A C 0.2327(14) 0.5400(12) 0.5324(11) 0.033(2) Uani 0.5 1 d D U P A 2
H51A H 0.211625 0.525613 0.464147 0.039 Uiso 0.5 1 calc R . P A 2
C52A C 0.299(2) 0.4170(15) 0.5879(16) 0.042(3) Uani 0.5 1 d D U P A 2
H52C H 0.310229 0.425669 0.660548 0.050 Uiso 0.5 1 calc R . P A 2
H52D H 0.248674 0.359559 0.592617 0.050 Uiso 0.5 1 calc R . P A 2
C53A C 0.1083(14) 0.6000(13) 0.5998(13) 0.055(3) Uani 0.5 1 d D U P A 2
H53D H 0.126478 0.617785 0.666217 0.082 Uiso 0.5 1 calc GR . P A 2
H53E H 0.054168 0.545566 0.615565 0.082 Uiso 0.5 1 calc GR . P A 2
H53F H 0.065634 0.674576 0.560297 0.082 Uiso 0.5 1 calc GR . P A 2
C61A C 0.5581(16) 0.4039(14) 0.2703(12) 0.063(3) Uani 0.5 1 d D U P A 2
H61A H 0.580529 0.321565 0.247668 0.075 Uiso 0.5 1 calc R . P A 2
C62A C 0.4103(16) 0.4602(14) 0.2846(12) 0.072(3) Uani 0.5 1 d D U P A 2
H62C H 0.383086 0.477058 0.213558 0.087 Uiso 0.5 1 calc R . P A 2
H62D H 0.370747 0.398760 0.325596 0.087 Uiso 0.5 1 calc R . P A 2
C63A C 0.612(2) 0.4834(18) 0.1901(14) 0.077(4) Uani 0.5 1 d D U P A 2
H63D H 0.701795 0.446765 0.171954 0.116 Uiso 0.5 1 calc GR . P A 2
H63E H 0.598928 0.560049 0.217698 0.116 Uiso 0.5 1 calc GR . P A 2
H63F H 0.570431 0.497208 0.126653 0.116 Uiso 0.5 1 calc GR . P A 2
C90A C 0.80605(2) 0.75574(2) 0.20868(2) 0.028(2) Uani 0.453(11) 1 d D U P D 2
C91A C 0.6872(14) 0.8151(10) 0.1716(6) 0.029(3) Uani 0.453(11) 1 d D U P D 2
H91A H 0.620428 0.777939 0.187622 0.034 Uiso 0.453(11) 1 calc R . P D 2
C92A C 0.670(2) 0.9285(12) 0.1113(9) 0.034(3) Uani 0.453(11) 1 d D U P D 2
H92A H 0.592073 0.967861 0.086691 0.041 Uiso 0.453(11) 1 calc R . P D 2
C93A C 0.7716(19) 0.9837(15) 0.0875(11) 0.038(4) Uani 0.453(11) 1 d D U P D 2
H93A H 0.759263 1.059954 0.046959 0.045 Uiso 0.453(11) 1 calc R . P D 2
C94A C 0.8867(19) 0.9295(14) 0.1217(11) 0.038(3) Uani 0.453(11) 1 d D U P D 2
H94A H 0.952178 0.968273 0.104777 0.046 Uiso 0.453(11) 1 calc R . P D 2
C95A C 0.9068(15) 0.8131(13) 0.1838(8) 0.035(3) Uani 0.453(11) 1 d D U P D 2
C96A C 1.0255(17) 0.7507(15) 0.2225(10) 0.042(4) Uani 0.453(11) 1 d D U P D 2
H96A H 1.094118 0.785280 0.207844 0.050 Uiso 0.453(11) 1 calc R . P D 2
C97A C 1.0359(17) 0.6404(14) 0.2808(10) 0.038(3) Uani 0.453(11) 1 d D U P D 2
H97A H 1.112325 0.597902 0.306919 0.046 Uiso 0.453(11) 1 calc R . P D 2
C98A C 0.9316(15) 0.5900(11) 0.3019(8) 0.027(2) Uani 0.453(11) 1 d D U P D 2
C99A C 0.9480(17) 0.4611(13) 0.3621(14) 0.035(3) Uani 0.453(11) 1 d D 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 O1 2.034(3) . ?
Cu1 O2 2.418(4) . ?
Cu1 O3 2.361(4) . ?
Cu1 N1 2.005(3) . ?
Cu1 N2 2.038(4) . ?
Cu1 N3 1.994(3) . ?
Cu2 O4 2.399(7) . ?
Cu2 O5 2.069(11) . ?
Cu2 O6 2.385(6) . ?
Cu2 N4 2.082(11) . ?
Cu2 N5 2.120(9) . ?
Cu2 N6 2.133(7) . ?
Cu2 O4A 2.297(8) . ?
Cu2 O5A 1.995(12) . ?
Cu2 O6A 2.235(8) . ?
Cu2 N4A 2.036(12) . ?
Cu2 N5A 1.900(8) . ?
Cu2 N6A 1.905(9) . ?
O1 C12 1.441(5) . ?
O2 C22 1.429(8) . ?
O3 C32 1.426(6) . ?
O7 C79 1.199(6) . ?
O8 C89 1.267(7) . ?
O10 C109 1.239(7) . ?
O77 C79 1.233(6) . ?
O88 C89 1.248(7) . ?
O101 C109 1.241(7) . ?
N1 C11 1.472(5) . ?
N2 C21 1.468(9) . ?
N3 C31 1.485(6) . ?
N7 C70 1.351(7) . ?
N7 C78 1.320(7) . ?
N8 C80 1.380(7) . ?
N8 C88 1.310(8) . ?
N10 C100 1.377(6) . ?
N10 C108 1.317(6) . ?
C11 C12 1.504(6) . ?
C11 C13 1.529(6) . ?
C21 C22 1.509(10) . ?
C21 C23 1.525(8) . ?
C31 C32 1.515(7) . ?
C31 C33 1.518(6) . ?
C70 C71 1.414(8) . ?
C70 C75 1.416(8) . ?
C71 C72 1.368(10) . ?
C72 C73 1.374(11) . ?
C73 C74 1.368(11) . ?
C74 C75 1.419(9) . ?
C75 C76 1.411(9) . ?
C76 C77 1.344(8) . ?
C77 C78 1.414(7) . ?
C78 C79 1.527(7) . ?
C80 C81 1.415(9) . ?
C80 C85 1.407(8) . ?
C81 C82 1.353(8) . ?
C82 C83 1.420(8) . ?
C83 C84 1.354(9) . ?
C84 C85 1.406(8) . ?
C85 C86 1.392(9) . ?
C86 C87 1.368(8) . ?
C87 C88 1.406(9) . ?
C88 C89 1.527(7) . ?
C100 C101 1.413(7) . ?
C100 C105 1.415(7) . ?
C101 C102 1.357(8) . ?
C102 C103 1.395(10) . ?
C103 C104 1.355(10) . ?
C104 C105 1.417(8) . ?
C105 C106 1.399(8) . ?
C106 C107 1.357(8) . ?
C107 C108 1.416(7) . ?
C108 C109 1.530(7) . ?
O4 C42 1.427(12) . ?
O5 C52 1.435(14) . ?
O6 C62 1.381(11) . ?
O9 C99 1.253(11) . ?
O99 C99 1.245(11) . ?
N4 C41 1.498(12) . ?
N5 C51 1.500(13) . ?
N6 C61 1.530(12) . ?
N9 C90 1.375(11) . ?
N9 C98 1.319(11) . ?
C41 C42 1.493(13) . ?
C41 C43 1.525(12) . ?
C51 C52 1.492(14) . ?
C51 C53 1.532(16) . ?
C61 C62 1.502(14) . ?
C61 C63 1.494(12) . ?
C90 C91 1.425(13) . ?
C90 C95 1.410(13) . ?
C91 C92 1.369(12) . ?
C92 C93 1.383(13) . ?
C93 C94 1.369(13) . ?
C94 C95 1.432(12) . ?
C95 C96 1.407(13) . ?
C96 C97 1.374(12) . ?
C97 C98 1.406(12) . ?
C98 C99 1.530(11) . ?
O4A C42A 1.413(13) . ?
O5A C52A 1.433(13) . ?
O6A C62A 1.362(14) . ?
O9A C99A 1.229(16) . ?
O99A C99A 1.278(16) . ?
N4A C41A 1.503(16) . ?
N5A C51A 1.492(11) . ?
N6A C61A 1.500(15) . ?
N9A C90A 1.372(9) . ?
N9A C98A 1.329(13) . ?
C41A C42A 1.468(16) . ?
C41A C43A 1.514(14) . ?
C51A C52A 1.517(14) . ?
C51A C53A 1.516(13) . ?
C61A C62A 1.555(17) . ?
C61A C63A 1.422(17) . ?
C90A C91A 1.413(13) . ?
C90A C95A 1.414(14) . ?
C91A C92A 1.384(13) . ?
C92A C93A 1.404(16) . ?
C93A C94A 1.354(16) . ?
C94A C95A 1.421(14) . ?
C95A C96A 1.426(15) . ?
C96A C97A 1.349(14) . ?
C97A C98A 1.397(15) . ?
C98A C99A 1.534(14) . ?

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 Cu1 O2 88.24(15) . . ?
O1 Cu1 O3 101.38(18) . . ?
O1 Cu1 N2 166.43(16) . . ?
O3 Cu1 O2 168.61(17) . . ?
N1 Cu1 O1 83.21(12) . . ?
N1 Cu1 O2 97.25(14) . . ?
N1 Cu1 O3 90.01(13) . . ?
N1 Cu1 N2 93.82(15) . . ?
N2 Cu1 O2 78.97(16) . . ?
N2 Cu1 O3 91.84(19) . . ?
N3 Cu1 O1 90.79(13) . . ?
N3 Cu1 O2 93.96(14) . . ?
N3 Cu1 O3 79.95(13) . . ?
N3 Cu1 N1 167.10(14) . . ?
N3 Cu1 N2 94.57(15) . . ?
O5 Cu2 O4 96.3(6) . . ?
O5 Cu2 O6 97.1(6) . . ?
O5 Cu2 N4 173.5(7) . . ?
O5 Cu2 N5 78.4(5) . . ?
O5 Cu2 N6 95.6(4) . . ?
O6 Cu2 O4 165.3(2) . . ?
N4 Cu2 O4 77.5(4) . . ?
N4 Cu2 O6 89.3(3) . . ?
N4 Cu2 N5 98.4(6) . . ?
N4 Cu2 N6 86.7(6) . . ?
N5 Cu2 O4 78.7(4) . . ?
N5 Cu2 O6 110.1(4) . . ?
N5 Cu2 N6 170.0(4) . . ?
N6 Cu2 O4 94.1(3) . . ?
N6 Cu2 O6 78.5(3) . . ?
O5A Cu2 O4A 84.6(7) . . ?
O5A Cu2 O6A 91.0(7) . . ?
O5A Cu2 N4A 164.4(8) . . ?
O6A Cu2 O4A 175.7(3) . . ?
N4A Cu2 O4A 80.3(5) . . ?
N4A Cu2 O6A 104.0(5) . . ?
N5A Cu2 O4A 113.2(3) . . ?
N5A Cu2 O5A 88.3(4) . . ?
N5A Cu2 O6A 66.3(3) . . ?
N5A Cu2 N4A 94.0(6) . . ?
N5A Cu2 N6A 150.6(4) . . ?
N6A Cu2 O4A 93.2(4) . . ?
N6A Cu2 O5A 81.2(6) . . ?
N6A Cu2 O6A 86.4(4) . . ?
N6A Cu2 N4A 103.5(6) . . ?
C12 O1 Cu1 109.4(2) . . ?
C22 O2 Cu1 101.4(3) . . ?
C32 O3 Cu1 103.4(3) . . ?
C11 N1 Cu1 108.9(2) . . ?
C21 N2 Cu1 113.7(3) . . ?
C31 N3 Cu1 110.8(3) . . ?
C78 N7 C70 118.2(5) . . ?
C88 N8 C80 118.0(5) . . ?
C108 N10 C100 117.7(4) . . ?
N1 C11 C12 107.4(3) . . ?
N1 C11 C13 112.6(4) . . ?
C12 C11 C13 110.1(4) . . ?
O1 C12 C11 107.2(3) . . ?
N2 C21 C22 108.8(5) . . ?
N2 C21 C23 112.6(6) . . ?
C22 C21 C23 110.6(7) . . ?
O2 C22 C21 112.6(5) . . ?
N3 C31 C32 109.2(4) . . ?
N3 C31 C33 112.3(4) . . ?
C32 C31 C33 111.5(4) . . ?
O3 C32 C31 107.8(4) . . ?
N7 C70 C71 118.8(6) . . ?
N7 C70 C75 123.0(5) . . ?
C71 C70 C75 118.2(6) . . ?
C72 C71 C70 119.8(7) . . ?
C71 C72 C73 122.1(7) . . ?
C74 C73 C72 120.5(7) . . ?
C73 C74 C75 119.5(6) . . ?
C70 C75 C74 120.0(6) . . ?
C76 C75 C70 117.3(5) . . ?
C76 C75 C74 122.7(6) . . ?
C77 C76 C75 118.7(5) . . ?
C76 C77 C78 120.8(5) . . ?
N7 C78 C77 122.0(5) . . ?
N7 C78 C79 118.4(4) . . ?
C77 C78 C79 119.6(5) . . ?
O7 C79 O77 125.0(6) . . ?
O7 C79 C78 120.0(4) . . ?
O77 C79 C78 115.0(5) . . ?
N8 C80 C81 119.0(5) . . ?
N8 C80 C85 122.0(6) . . ?
C85 C80 C81 119.0(5) . . ?
C82 C81 C80 120.8(5) . . ?
C81 C82 C83 120.1(6) . . ?
C84 C83 C82 119.8(5) . . ?
C83 C84 C85 121.3(6) . . ?
C84 C85 C80 118.9(6) . . ?
C86 C85 C80 117.5(5) . . ?
C86 C85 C84 123.5(6) . . ?
C87 C86 C85 120.5(6) . . ?
C86 C87 C88 118.3(6) . . ?
N8 C88 C87 123.7(5) . . ?
N8 C88 C89 119.1(5) . . ?
C87 C88 C89 117.2(5) . . ?
O8 C89 C88 117.5(5) . . ?
O88 C89 O8 126.3(5) . . ?
O88 C89 C88 116.2(5) . . ?
N10 C100 C101 119.1(5) . . ?
N10 C100 C105 121.7(5) . . ?
C101 C100 C105 119.2(5) . . ?
C102 C101 C100 119.8(5) . . ?
C101 C102 C103 121.4(6) . . ?
C104 C103 C102 120.4(6) . . ?
C103 C104 C105 120.3(6) . . ?
C100 C105 C104 118.9(5) . . ?
C106 C105 C100 118.2(5) . . ?
C106 C105 C104 123.0(5) . . ?
C107 C106 C105 120.0(5) . . ?
C106 C107 C108 118.6(5) . . ?
N10 C108 C107 123.8(5) . . ?
N10 C108 C109 117.3(4) . . ?
C107 C108 C109 118.8(4) . . ?
O10 C109 O101 125.7(6) . . ?
O10 C109 C108 119.3(5) . . ?
O101 C109 C108 115.0(5) . . ?
C42 O4 Cu2 105.0(6) . . ?
C52 O5 Cu2 112.7(11) . . ?
C62 O6 Cu2 104.6(6) . . ?
C41 N4 Cu2 112.5(7) . . ?
C51 N5 Cu2 110.0(7) . . ?
C61 N6 Cu2 111.3(5) . . ?
C98 N9 C90 117.5(9) . . ?
N4 C41 C43 113.0(9) . . ?
C42 C41 N4 108.1(10) . . ?
C42 C41 C43 113.8(9) . . ?
O4 C42 C41 112.3(9) . . ?
N5 C51 C53 113.2(11) . . ?
C52 C51 N5 103.1(11) . . ?
C52 C51 C53 113.3(12) . . ?
O5 C52 C51 108.7(11) . . ?
C62 C61 N6 109.8(7) . . ?
C63 C61 N6 113.3(8) . . ?
C63 C61 C62 109.7(8) . . ?
O6 C62 C61 113.7(9) . . ?
N9 C90 C91 118.2(10) . . ?
N9 C90 C95 123.3(10) . . ?
C95 C90 C91 118.5(9) . . ?
C92 C91 C90 120.0(12) . . ?
C91 C92 C93 122.1(13) . . ?
C94 C93 C92 119.6(12) . . ?
C93 C94 C95 120.6(12) . . ?
C90 C95 C94 119.2(11) . . ?
C96 C95 C90 116.9(10) . . ?
C96 C95 C94 123.9(11) . . ?
C97 C96 C95 119.7(11) . . ?
C96 C97 C98 119.3(10) . . ?
N9 C98 C97 123.3(9) . . ?
N9 C98 C99 117.8(8) . . ?
C97 C98 C99 118.8(8) . . ?
O9 C99 C98 119.7(8) . . ?
O99 C99 O9 126.3(8) . . ?
O99 C99 C98 114.1(8) . . ?
C42A O4A Cu2 106.2(7) . . ?
C52A O5A Cu2 107.8(9) . . ?
C62A O6A Cu2 99.3(7) . . ?
C41A N4A Cu2 109.3(9) . . ?
C51A N5A Cu2 107.3(6) . . ?
C61A N6A Cu2 112.6(8) . . ?
C98A N9A C90A 116.5(11) . . ?
N4A C41A C43A 111.0(12) . . ?
C42A C41A N4A 110.5(11) . . ?
C42A C41A C43A 112.1(11) . . ?
O4A C42A C41A 111.8(10) . . ?
N5A C51A C52A 109.7(11) . . ?
N5A C51A C53A 112.3(8) . . ?
C53A C51A C52A 111.6(9) . . ?
O5A C52A C51A 107.9(10) . . ?
N6A C61A C62A 107.7(10) . . ?
C63A C61A N6A 110.2(12) . . ?
C63A C61A C62A 106.8(13) . . ?
O6A C62A C61A 117.1(13) . . ?
N9A C90A C91A 118.0(9) . . ?
N9A C90A C95A 122.5(10) . . ?
C91A C90A C95A 119.5(9) . . ?
C92A C91A C90A 119.9(13) . . ?
C91A C92A C93A 119.5(15) . . ?
C94A C93A C92A 122.1(14) . . ?
C93A C94A C95A 119.5(15) . . ?
C90A C95A C94A 119.4(13) . . ?
C90A C95A C96A 118.1(11) . . ?
C94A C95A C96A 122.6(13) . . ?
C97A C96A C95A 118.5(14) . . ?
C96A C97A C98A 119.8(13) . . ?
N9A C98A C97A 124.6(11) . . ?
N9A C98A C99A 116.2(10) . . ?
C97A C98A C99A 119.1(11) . . ?
O9A C99A O99A 125.0(12) . . ?
O9A C99A C98A 120.9(12) . . ?
O99A C99A C98A 114.1(13) . . ?

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
_geom_hbond_publ_flag
O1 H1 O8 0.78(6) 1.83(6) 2.610(5) 177(6) . yes
O2 H2 O7 0.81(7) 1.85(7) 2.656(6) 174(7) . yes
O3 H3 O9 0.843(15) 2.16(3) 2.975(9) 162(9) 1_465 yes
O3 H3 O99A 0.843(15) 1.73(5) 2.497(10) 151(9) 1_465 yes
N1 H1B O99 0.89 2.10 2.977(7) 170.9 1_465 yes
N2 H2A O10 0.89 2.02 2.906(6) 177.5 1_465 yes
N3 H3B O88 0.89 2.07 2.924(5) 160.7 . yes
O4 H4 N8 0.860(14) 2.21(6) 2.914(8) 138(7) . yes
O5 H5 O101 0.861(13) 2.03(11) 2.582(13) 121(11) . yes
O6 H6 O77 0.82 1.76 2.571(8) 168.2 . yes
N5 H5A O8 0.89 2.04 2.685(12) 128.1 . yes
N6 H6A O9 0.89 2.01 2.860(12) 158.4 . yes
O5A H5AA O101 0.856(14) 1.55(2) 2.406(16) 179(7) . yes
O6A H6AA O77 0.82 1.89 2.614(11) 147.0 . yes
N6A H6AB O9A 0.89 2.06 2.924(15) 164.8 . yes

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.479
_oxdiff_exptl_absorpt_empirical_full_min 0.738
####################################################################### 
# 
# 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_10e
_database_code_depnum_ccdc_archive 'CCDC 2077006'
loop_
_audit_author_name
_audit_author_address
'Barbara Modec'
;University of Ljubljana
Slovenia
;
_audit_update_record             
;
2022-02-17 deposited with the CCDC.	2022-03-18 downloaded from the CCDC.
;
_audit_creation_date             2022-02-17
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H33 Cu N3 O3, 2(C10 H6 N O2)'
_chemical_formula_sum            'C32 H45 Cu N5 O7'
_chemical_formula_weight         675.27
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   14.1491(5)
_cell_length_b                   21.7604(9)
_cell_length_c                   23.6679(9)
_cell_angle_alpha                110.376(4)
_cell_angle_beta                 100.665(3)
_cell_angle_gamma                91.832(3)
_cell_volume                     6676.3(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9796
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      26.9270
_cell_measurement_theta_min      2.5530
_shelx_estimated_absorpt_T_max   0.972
_shelx_estimated_absorpt_T_min   0.871
_exptl_absorpt_coefficient_mu    0.707
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54447
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             2856
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0583
_diffrn_reflns_av_unetI/netI     0.1286
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.861
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            68809
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.861
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.391
_diffrn_reflns_theta_min         2.372
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.861
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -52.00 -20.00   1.00   90.00    --   14.21 -37.00  60.00   32
  2  ω     17.00  89.00   1.00   90.00    --   14.21  37.00-120.00   72
  3  ω    -40.00  46.00   1.00   90.00    --   14.21 -77.00 120.00   86
  4  ω      6.00  52.00   1.00   90.00    --   14.21  37.00  60.00   46
  5  ω    -11.00  87.00   1.00   90.00    --   14.21  57.00 -30.00   98
  6  ω    -26.00  15.00   1.00   90.00    --  -14.52 -77.00   0.00   41
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0447708000
_diffrn_orient_matrix_UB_12      0.0190280000
_diffrn_orient_matrix_UB_13      0.0163017000
_diffrn_orient_matrix_UB_21      0.0225533000
_diffrn_orient_matrix_UB_22      -0.0184863000
_diffrn_orient_matrix_UB_23      -0.0240267000
_diffrn_orient_matrix_UB_31      -0.0108587000
_diffrn_orient_matrix_UB_32      0.0227737000
_diffrn_orient_matrix_UB_33      -0.0150290000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                16450
_reflns_number_total             34714
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.882
_refine_diff_density_min         -0.668
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1654
_refine_ls_number_reflns         34714
_refine_ls_number_restraints     28
_refine_ls_R_factor_all          0.1656
_refine_ls_R_factor_gt           0.0684
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0600P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1354
_refine_ls_wR_factor_ref         0.1749
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O10-H10
 0.85 with sigma of 0.01
 O11-H11A
 0.85 with sigma of 0.01
 O5-H5
 0.85 with sigma of 0.01
 O4-H4
 0.85 with sigma of 0.01
 O8-H8
 0.85 with sigma of 0.01
 O7-H7
 0.85 with sigma of 0.01
 O2-H2
 0.85 with sigma of 0.01
 O1-H1
 0.85 with sigma of 0.01
 C102-H10
 1.906992 with sigma of 0.02
 Cu4-H10
 3.077491 with sigma of 0.02
 C112-H11A
 1.912863 with sigma of 0.02
 Cu4-H11A
 2.704114 with sigma of 0.02
 C52-H5
 1.929347 with sigma of 0.02
 Cu2-H5
 3.128236 with sigma of 0.02
 C42-H4
 1.905599 with sigma of 0.02
 Cu2-H4
 2.707278 with sigma of 0.02
 C82-H8
 1.908404 with sigma of 0.02
 Cu3-H8
 3.134538 with sigma of 0.02
 C72-H7
 1.897516 with sigma of 0.02
 Cu3-H7
 2.728809 with sigma of 0.02
 C22-H2
 1.913066 with sigma of 0.02
 Cu1-H2
 2.708558 with sigma of 0.02
 C12-H1
 1.913707 with sigma of 0.02
 Cu1-H1
 3.096232 with sigma of 0.02
 C72-C71A \\sim C72-C71
 with sigma of 0.02
 N7-C71A \\sim N7-C71
 with sigma of 0.02
 C71A-C73A \\sim C73-C71
 with sigma of 0.02
 C74-C73 \\sim C73A-C74A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C72) = Uanis(C71A) = Uanis(C71) = Uanis(C73A) = Uanis(C74A) = Uanis(C73)
= Uanis(C74)
4. Others
 Sof(H72C)=Sof(H72D)=Sof(C71A)=Sof(H71A)=Sof(C73A)=Sof(H73C)=Sof(H73D)=
 Sof(C74A)=Sof(H74D)=Sof(H74E)=Sof(H74F)=1-FVAR(1)
 Sof(H72A)=Sof(H72B)=Sof(C71)=Sof(H71)=Sof(C73)=Sof(H73A)=Sof(H73B)=Sof(C74)=
 Sof(H74A)=Sof(H74B)=Sof(H74C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C11(H11), C21(H21), C31(H31), C41(H41), C51(H51), C61(H61), C81(H81),
 C91(H91), C101(H101), C111(H111), C121(H121), C71(H71), C71A(H71A)
5.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2A,H2B), N3(H3A,H3B), N4(H4A,H4B), N5(H5A,H5B), N6(H6A,H6B),
 N7(H7A,H7B), N8(H8A,H8B), N9(H9A,H9B), N10(H10A,H10B), N11(H11B,H11C),
 N12(H12C,H12D), C12(H12A,H12B), C13(H13A,H13B), C22(H22A,H22B), C23(H23A,H23B),
  C32(H32A,H32B), C33(H33A,H33B), C42(H42A,H42B), C43(H43A,H43B), C52(H52A,
 H52B), C53(H53A,H53B), C62(H62A,H62B), C63(H63A,H63B), C72(H72A,H72B),
 C72(H72C,H72D), C82(H82A,H82B), C83(H83A,H83B), C92(H92A,H92B), C93(H93A,H93B),
  C102(H10C,H10D), C103(H10E,H10F), C112(H11D,H11E), C113(H11F,H11G), C122(H12E,
 H12F), C123(H12G,H12H), C73(H73A,H73B), C73A(H73C,H73D)
5.c Aromatic/amide H refined with riding coordinates:
 C131(H131), C132(H132), C133(H133), C134(H134), C136(H136), C137(H137),
 C141(H141), C142(H142), C143(H143), C144(H144), C146(H146), C147(H147),
 C151(H151), C152(H152), C153(H153), C154(H154), C156(H156), C157(H157),
 C161(H161), C162(H162), C163(H163), C164(H164), C166(H166), C167(H167),
 C171(H171), C172(H172), C173(H173), C174(H174), C176(H176), C177(H177),
 C181(H181), C182(H182), C183(H183), C184(H184), C186(H186), C187(H187),
 C191(H191), C192(H192), C193(H193), C194(H194), C196(H196), C197(H197),
 C201(H201), C202(H202), C203(H203), C204(H204), C206(H206), C207(H207)
5.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C24(H24A,H24B,H24C), C34(H34A,H34B,H34C), C44(H44A,H44B,
 H44C), C54(H54A,H54B,H54C), C64(H64A,H64B,H64C), C84(H84A,H84B,H84C), C94(H94A,
 H94B,H94C), C104(H10G,H10H,H10I), C114(H11H,H11I,H11J), C124(H12I,H12J,H12K),
 C74(H74A,H74B,H74C), C74A(H74D,H74E,H74F)
5.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O6(H6), O9(H9), O12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 1.27111(3) -0.23349(2) 0.22880(2) 0.03030(12) Uani 1 1 d D . . . .
Cu2 Cu 0.80112(3) -0.23083(2) 0.30483(2) 0.03570(13) Uani 1 1 d D . . . .
Cu3 Cu 0.26292(3) 0.48877(2) 0.53367(2) 0.03097(12) Uani 1 1 d D . . . .
Cu4 Cu -0.26376(3) 0.99450(2) 0.96928(2) 0.02891(12) Uani 1 1 d D . . . .
O1 O 1.38159(19) -0.23316(12) 0.16571(13) 0.0360(7) Uani 1 1 d D . . . .
H1 H 1.4244(17) -0.2588(9) 0.1525(16) 0.054 Uiso 1 1 d DR . . . .
O2 O 1.15600(18) -0.21537(12) 0.17564(13) 0.0344(6) Uani 1 1 d D . . . .
H2 H 1.1274(15) -0.1796(7) 0.1824(14) 0.052 Uiso 1 1 d DR . . . .
O3 O 1.2012(2) -0.20167(14) 0.32464(15) 0.0476(8) Uani 1 1 d . . . . .
H3 H 1.156663 -0.231325 0.311503 0.071 Uiso 1 1 calc GR . . . .
O4 O 0.9104(2) -0.25311(14) 0.35851(15) 0.0514(8) Uani 1 1 d D . . . .
H4 H 0.9384(17) -0.2893(7) 0.3500(15) 0.077 Uiso 1 1 d DR . . . .
O5 O 0.6894(2) -0.23494(13) 0.36765(14) 0.0424(7) Uani 1 1 d D . . . .
H5 H 0.6434(16) -0.2105(9) 0.3787(16) 0.064 Uiso 1 1 d DR . . . .
O6 O 0.8626(2) -0.26158(14) 0.20486(15) 0.0469(8) Uani 1 1 d . . . . .
H6 H 0.907417 -0.232033 0.219117 0.070 Uiso 1 1 calc GR . . . .
O7 O 0.3712(2) 0.45281(13) 0.57685(14) 0.0443(7) Uani 1 1 d D . . . .
H7 H 0.3983(17) 0.4167(8) 0.5628(13) 0.067 Uiso 1 1 d DR . . . .
O8 O 0.1461(2) 0.47681(13) 0.59121(14) 0.0426(7) Uani 1 1 d D . . . .
H8 H 0.1027(16) 0.5027(9) 0.6051(16) 0.064 Uiso 1 1 d DR . . . .
O9 O 0.3344(2) 0.48413(14) 0.44519(15) 0.0504(8) Uani 1 1 d . . . . .
H9 H 0.379972 0.512944 0.461628 0.076 Uiso 1 1 calc GR . . . .
O10 O -0.16535(19) 0.98611(12) 0.89862(13) 0.0374(7) Uani 1 1 d D . . . .
H10 H -0.1219(18) 0.9609(9) 0.8863(16) 0.056 Uiso 1 1 d DR . . . .
O11 O -0.38054(18) 1.00566(12) 0.91339(13) 0.0367(7) Uani 1 1 d D . . . .
H11A H -0.4112(15) 1.0408(7) 0.9182(15) 0.055 Uiso 1 1 d DR . . . .
O12 O -0.3221(2) 1.03720(14) 1.07322(16) 0.0498(8) Uani 1 1 d . . . . .
H12 H -0.362328 1.004814 1.059554 0.075 Uiso 1 1 calc GR . . . .
O13 O 1.5269(2) -0.30579(13) 0.18194(15) 0.0505(8) Uani 1 1 d . . . . .
O14 O 1.0826(2) -0.31889(13) 0.27434(15) 0.0516(9) Uani 1 1 d . . . . .
O15 O 0.9862(2) -0.14771(12) 0.25731(15) 0.0493(8) Uani 1 1 d . . . . .
O16 O 0.54579(19) -0.16053(12) 0.34608(13) 0.0425(7) Uani 1 1 d . . . . .
O17 O 0.54244(19) 0.40231(13) 0.48954(14) 0.0460(8) Uani 1 1 d . . . . .
O18 O 0.0081(2) 0.56171(14) 0.59194(16) 0.0597(9) Uani 1 1 d . . . . .
O19 O -0.01559(19) 0.91923(12) 0.92282(14) 0.0420(7) Uani 1 1 d . . . . .
O20 O -0.5621(2) 1.08114(13) 0.97175(16) 0.0534(9) Uani 1 1 d . . . . .
O131 O 1.4077(2) -0.37857(14) 0.17607(17) 0.0601(9) Uani 1 1 d . . . . .
O141 O 0.9677(2) -0.36168(13) 0.30736(16) 0.0541(9) Uani 1 1 d . . . . .
O151 O 1.10739(19) -0.10393(12) 0.23062(14) 0.0414(7) Uani 1 1 d . . . . .
O161 O 0.6688(2) -0.08778(13) 0.35716(15) 0.0487(8) Uani 1 1 d . . . . .
O171 O 0.4176(2) 0.34867(12) 0.50380(14) 0.0434(7) Uani 1 1 d . . . . .
O181 O 0.1393(2) 0.63151(14) 0.61362(16) 0.0549(9) Uani 1 1 d . . . . .
O191 O -0.12513(19) 0.84968(13) 0.93275(14) 0.0425(7) Uani 1 1 d . . . . .
O201 O -0.43337(19) 1.12004(12) 0.94865(14) 0.0425(8) Uani 1 1 d . . . . .
N1 N 1.3156(2) -0.13677(13) 0.25915(14) 0.0280(7) Uani 1 1 d . . . . .
H1A H 1.266545 -0.113494 0.268927 0.034 Uiso 1 1 calc R . . . .
H1B H 1.362189 -0.126186 0.292868 0.034 Uiso 1 1 calc R . . . .
N2 N 1.2140(2) -0.32688(14) 0.18334(15) 0.0351(8) Uani 1 1 d . . . . .
H2A H 1.260412 -0.352137 0.171789 0.042 Uiso 1 1 calc R . . . .
H2B H 1.186748 -0.341457 0.207930 0.042 Uiso 1 1 calc R . . . .
N3 N 1.3698(2) -0.25849(14) 0.28818(15) 0.0312(7) Uani 1 1 d . . . . .
H3A H 1.395574 -0.293948 0.267299 0.037 Uiso 1 1 calc R . . . .
H3B H 1.417022 -0.225698 0.306851 0.037 Uiso 1 1 calc R . . . .
N4 N 0.8644(2) -0.13869(15) 0.35310(18) 0.0468(10) Uani 1 1 d . . . . .
H4A H 0.891970 -0.123638 0.328933 0.056 Uiso 1 1 calc R . . . .
H4B H 0.819819 -0.112385 0.366154 0.056 Uiso 1 1 calc R . . . .
N5 N 0.7542(2) -0.32643(14) 0.26969(15) 0.0387(9) Uani 1 1 d . . . . .
H5A H 0.707370 -0.334304 0.236463 0.046 Uiso 1 1 calc R . . . .
H5B H 0.802414 -0.349609 0.257998 0.046 Uiso 1 1 calc R . . . .
N6 N 0.7019(2) -0.20154(15) 0.25005(16) 0.0400(9) Uani 1 1 d . . . . .
H6A H 0.654464 -0.233951 0.229887 0.048 Uiso 1 1 calc R . . . .
H6B H 0.676507 -0.167023 0.272908 0.048 Uiso 1 1 calc R . . . .
N7 N 0.3281(2) 0.57502(16) 0.59621(17) 0.0451(9) Uani 1 1 d D . . . .
H7A H 0.366379 0.594323 0.579965 0.054 Uiso 1 1 calc R . . A .
H7B H 0.284482 0.602009 0.609551 0.054 Uiso 1 1 calc R . . A .
N8 N 0.2060(2) 0.39480(14) 0.48713(15) 0.0368(8) Uani 1 1 d . . . . .
H8A H 0.159703 0.392956 0.455303 0.044 Uiso 1 1 calc R . . . .
H8B H 0.251607 0.370594 0.472502 0.044 Uiso 1 1 calc R . . . .
N9 N 0.1675(2) 0.53222(15) 0.48913(16) 0.0416(9) Uani 1 1 d . . . . .
H9A H 0.118157 0.502647 0.465273 0.050 Uiso 1 1 calc R . . . .
H9B H 0.144269 0.564157 0.516579 0.050 Uiso 1 1 calc R . . . .
N10 N -0.2226(2) 1.08992(14) 0.99067(15) 0.0323(8) Uani 1 1 d . . . . .
H10A H -0.271403 1.113407 1.000522 0.039 Uiso 1 1 calc R . . . .
H10B H -0.173637 1.103389 1.023255 0.039 Uiso 1 1 calc R . . . .
N11 N -0.3197(2) 0.90010(14) 0.93339(15) 0.0312(7) Uani 1 1 d . . . . .
H11B H -0.273547 0.874251 0.922622 0.037 Uiso 1 1 calc R . . . .
H11C H -0.343571 0.889467 0.961394 0.037 Uiso 1 1 calc R . . . .
N12 N -0.1581(2) 0.97771(14) 1.03069(14) 0.0301(7) Uani 1 1 d . . . . .
H12C H -0.131445 0.942016 1.011206 0.036 Uiso 1 1 calc R . . . .
H12D H -0.112410 1.011665 1.045545 0.036 Uiso 1 1 calc R . . . .
N13 N 1.6359(2) -0.40735(15) 0.13791(16) 0.0372(8) Uani 1 1 d . . . . .
N14 N 1.1596(2) -0.43606(15) 0.24267(17) 0.0389(8) Uani 1 1 d . . . . .
N15 N 0.9283(2) -0.02610(14) 0.30861(16) 0.0342(8) Uani 1 1 d . . . . .
N16 N 0.4388(2) -0.05562(15) 0.38813(15) 0.0369(8) Uani 1 1 d . . . . .
N17 N 0.5795(2) 0.28842(15) 0.40474(16) 0.0348(8) Uani 1 1 d . . . . .
N18 N -0.0869(2) 0.66801(17) 0.64991(17) 0.0432(9) Uani 1 1 d . . . . .
N19 N 0.0985(2) 0.81895(14) 0.88772(15) 0.0308(7) Uani 1 1 d . . . . .
N20 N -0.6343(2) 1.19944(14) 0.99564(15) 0.0332(8) Uani 1 1 d . . . . .
C11 C 1.3526(3) -0.12041(17) 0.21061(19) 0.0320(9) Uani 1 1 d . . . . .
H11 H 1.298119 -0.128492 0.175743 0.038 Uiso 1 1 calc R . . . .
C12 C 1.4262(3) -0.16658(18) 0.1884(2) 0.0357(10) Uani 1 1 d D . . . .
H12A H 1.449520 -0.157347 0.155810 0.043 Uiso 1 1 calc R . . . .
H12B H 1.480923 -0.160437 0.221998 0.043 Uiso 1 1 calc R . . . .
C13 C 1.3946(3) -0.04891(17) 0.2310(2) 0.0377(10) Uani 1 1 d . . . . .
H13A H 1.448292 -0.039895 0.265816 0.045 Uiso 1 1 calc R . . . .
H13B H 1.419763 -0.042854 0.197678 0.045 Uiso 1 1 calc R . . . .
C14 C 1.3221(3) 0.00063(18) 0.2493(2) 0.0439(11) Uani 1 1 d . . . . .
H14A H 1.265772 -0.010417 0.216610 0.066 Uiso 1 1 calc GR . . . .
H14B H 1.350872 0.044033 0.256740 0.066 Uiso 1 1 calc GR . . . .
H14C H 1.303905 -0.000422 0.286089 0.066 Uiso 1 1 calc GR . . . .
C21 C 1.1408(3) -0.33105(19) 0.1286(2) 0.0416(11) Uani 1 1 d . . . . .
H21 H 1.174632 -0.328032 0.096879 0.050 Uiso 1 1 calc R . . . .
C22 C 1.0850(3) -0.27158(18) 0.1472(2) 0.0396(10) Uani 1 1 d D . . . .
H22A H 1.042648 -0.268296 0.111392 0.048 Uiso 1 1 calc R . . . .
H22B H 1.046178 -0.274779 0.176020 0.048 Uiso 1 1 calc R . . . .
C23 C 1.0724(4) -0.3942(2) 0.1011(2) 0.0602(14) Uani 1 1 d . . . . .
H23A H 1.023634 -0.391188 0.067769 0.072 Uiso 1 1 calc R . . . .
H23B H 1.039591 -0.398114 0.132467 0.072 Uiso 1 1 calc R . . . .
C24 C 1.1230(4) -0.4569(2) 0.0763(3) 0.0722(16) Uani 1 1 d . . . . .
H24A H 1.157648 -0.452770 0.046393 0.108 Uiso 1 1 calc GR . . . .
H24B H 1.075387 -0.494499 0.057430 0.108 Uiso 1 1 calc GR . . . .
H24C H 1.167321 -0.462398 0.109773 0.108 Uiso 1 1 calc GR . . . .
C31 C 1.3260(3) -0.2727(2) 0.3356(2) 0.0487(12) Uani 1 1 d . . . . .
H31 H 1.276665 -0.310367 0.313634 0.058 Uiso 1 1 calc R . . . .
C32 C 1.2752(4) -0.2159(2) 0.3665(2) 0.0547(13) Uani 1 1 d . . . . .
H32A H 1.246966 -0.225217 0.397328 0.066 Uiso 1 1 calc R . . . .
H32B H 1.321966 -0.177313 0.387476 0.066 Uiso 1 1 calc R . . . .
C33 C 1.3989(3) -0.2927(2) 0.3803(2) 0.0539(13) Uani 1 1 d . . . . .
H33A H 1.458527 -0.263714 0.392479 0.065 Uiso 1 1 calc R . . . .
H33B H 1.373880 -0.287085 0.417094 0.065 Uiso 1 1 calc R . . . .
C34 C 1.4207(3) -0.3634(2) 0.3528(2) 0.0574(14) Uani 1 1 d . . . . .
H34A H 1.444214 -0.369440 0.315926 0.086 Uiso 1 1 calc GR . . . .
H34B H 1.362744 -0.392436 0.343164 0.086 Uiso 1 1 calc GR . . . .
H34C H 1.468904 -0.373002 0.382000 0.086 Uiso 1 1 calc GR . . . .
C41 C 0.9381(4) -0.1377(2) 0.4065(3) 0.087(2) Uani 1 1 d . . . . .
H41 H 0.903947 -0.138223 0.438802 0.105 Uiso 1 1 calc R . . . .
C42 C 0.9834(4) -0.1990(2) 0.3883(3) 0.086(2) Uani 1 1 d D . . . .
H42A H 1.025399 -0.197820 0.360537 0.103 Uiso 1 1 calc R . . . .
H42B H 1.022396 -0.203982 0.424428 0.103 Uiso 1 1 calc R . . . .
C43 C 1.0125(5) -0.0782(3) 0.4341(3) 0.095(2) Uani 1 1 d . . . . .
H43A H 1.044044 -0.075153 0.401991 0.113 Uiso 1 1 calc R . . . .
H43B H 0.978996 -0.039135 0.447440 0.113 Uiso 1 1 calc R . . . .
C44 C 1.0886(7) -0.0772(4) 0.4872(4) 0.192(5) Uani 1 1 d . . . . .
H44A H 1.133856 -0.107759 0.472571 0.288 Uiso 1 1 calc GR . . . .
H44B H 1.059125 -0.089595 0.515624 0.288 Uiso 1 1 calc GR . . . .
H44C H 1.121764 -0.033635 0.507630 0.288 Uiso 1 1 calc GR . . . .
C51 C 0.7172(3) -0.34799(19) 0.3144(2) 0.0452(11) Uani 1 1 d . . . . .
H51 H 0.772096 -0.343202 0.348243 0.054 Uiso 1 1 calc R . . . .
C52 C 0.6460(3) -0.3032(2) 0.3411(2) 0.0495(13) Uani 1 1 d D . . . .
H52A H 0.589616 -0.307531 0.309158 0.059 Uiso 1 1 calc R . . . .
H52B H 0.625222 -0.315697 0.372820 0.059 Uiso 1 1 calc R . . . .
C53 C 0.6743(3) -0.42009(19) 0.2889(2) 0.0502(12) Uani 1 1 d . . . . .
H53A H 0.619950 -0.426292 0.255074 0.060 Uiso 1 1 calc R . . . .
H53B H 0.650090 -0.429940 0.320857 0.060 Uiso 1 1 calc R . . . .
C54 C 0.7469(4) -0.4687(2) 0.2660(2) 0.0635(15) Uani 1 1 d . . . . .
H54A H 0.773102 -0.458238 0.235384 0.095 Uiso 1 1 calc GR . . . .
H54B H 0.714867 -0.512685 0.248263 0.095 Uiso 1 1 calc GR . . . .
H54C H 0.798294 -0.465499 0.299953 0.095 Uiso 1 1 calc GR . . . .
C61 C 0.7461(4) -0.1832(2) 0.2050(2) 0.0537(13) Uani 1 1 d . . . . .
H61 H 0.801275 -0.150469 0.229233 0.064 Uiso 1 1 calc R . . . .
C62 C 0.7880(3) -0.2439(2) 0.1671(2) 0.0477(12) Uani 1 1 d . . . . .
H62A H 0.737331 -0.280352 0.147426 0.057 Uiso 1 1 calc R . . . .
H62B H 0.812995 -0.234789 0.135020 0.057 Uiso 1 1 calc R . . . .
C63 C 0.6834(4) -0.1523(2) 0.1689(3) 0.0656(16) Uani 1 1 d . . . . .
H63A H 0.623410 -0.180887 0.149471 0.079 Uiso 1 1 calc R . . . .
H63B H 0.714160 -0.149835 0.136281 0.079 Uiso 1 1 calc R . . . .
C64 C 0.6588(3) -0.08394(19) 0.2037(2) 0.0470(12) Uani 1 1 d . . . . .
H64A H 0.610115 -0.071052 0.177176 0.071 Uiso 1 1 calc GR . . . .
H64B H 0.715741 -0.053186 0.216927 0.071 Uiso 1 1 calc GR . . . .
H64C H 0.634896 -0.084277 0.239014 0.071 Uiso 1 1 calc GR . . . .
C72 C 0.4442(3) 0.5040(2) 0.6157(2) 0.0530(8) Uani 1 1 d D . . . .
H72A H 0.482284 0.518586 0.591659 0.064 Uiso 0.733(4) 1 calc R . P B 1
H72B H 0.486896 0.489642 0.644633 0.064 Uiso 0.733(4) 1 calc R . P B 1
H72C H 0.494300 0.505478 0.593024 0.064 Uiso 0.267(4) 1 calc R . P B 2
H72D H 0.473133 0.492497 0.650626 0.064 Uiso 0.267(4) 1 calc R . P B 2
C81 C 0.1651(3) 0.36764(18) 0.5276(2) 0.0415(11) Uani 1 1 d . . . . .
H81 H 0.218723 0.367632 0.560405 0.050 Uiso 1 1 calc R . . . .
C82 C 0.0963(3) 0.41269(19) 0.5579(2) 0.0455(11) Uani 1 1 d D . . . .
H82A H 0.042381 0.414759 0.526818 0.055 Uiso 1 1 calc R . . . .
H82B H 0.070989 0.395952 0.585696 0.055 Uiso 1 1 calc R . . . .
C83 C 0.1176(3) 0.29724(18) 0.4959(2) 0.0492(12) Uani 1 1 d . . . . .
H83A H 0.087377 0.285034 0.524617 0.059 Uiso 1 1 calc R . . . .
H83B H 0.067048 0.295271 0.461323 0.059 Uiso 1 1 calc R . . . .
C84 C 0.1872(3) 0.2476(2) 0.4728(2) 0.0577(14) Uani 1 1 d . . . . .
H84A H 0.213928 0.257365 0.442127 0.086 Uiso 1 1 calc GR . . . .
H84B H 0.153349 0.204086 0.455167 0.086 Uiso 1 1 calc GR . . . .
H84C H 0.238338 0.249856 0.506613 0.086 Uiso 1 1 calc GR . . . .
C91 C 0.2132(5) 0.5604(3) 0.4506(3) 0.0761(19) Uani 1 1 d . . . . .
H91 H 0.269842 0.586949 0.480920 0.091 Uiso 1 1 calc R . . . .
C92 C 0.2610(4) 0.5065(2) 0.4096(2) 0.0561(13) Uani 1 1 d . . . . .
H92A H 0.212775 0.469921 0.384076 0.067 Uiso 1 1 calc R . . . .
H92B H 0.289087 0.522986 0.382531 0.067 Uiso 1 1 calc R . . . .
C93 C 0.1731(7) 0.6062(3) 0.4306(4) 0.163(5) Uani 1 1 d . . . . .
H93A H 0.112667 0.584482 0.402532 0.195 Uiso 1 1 calc R . . . .
H93B H 0.214745 0.615362 0.405633 0.195 Uiso 1 1 calc R . . . .
C94 C 0.1510(4) 0.6697(2) 0.4691(3) 0.0771(18) Uani 1 1 d . . . . .
H94A H 0.102338 0.685757 0.445404 0.116 Uiso 1 1 calc GR . . . .
H94B H 0.208454 0.700224 0.484312 0.116 Uiso 1 1 calc GR . . . .
H94C H 0.127719 0.665226 0.503256 0.116 Uiso 1 1 calc GR . . . .
C101 C -0.1919(3) 1.10117(19) 0.93751(19) 0.0369(10) Uani 1 1 d . . . . .
H101 H -0.249429 1.092140 0.904458 0.044 Uiso 1 1 calc R . . . .
C102 C -0.1225(3) 1.05253(19) 0.9141(2) 0.0415(11) Uani 1 1 d D . . . .
H10C H -0.105596 1.057412 0.877882 0.050 Uiso 1 1 calc R . . . .
H10D H -0.063777 1.061209 0.945421 0.050 Uiso 1 1 calc R . . . .
C103 C -0.1482(3) 1.17199(19) 0.9528(2) 0.0412(11) Uani 1 1 d . . . . .
H10E H -0.090786 1.181434 0.985295 0.049 Uiso 1 1 calc R . . . .
H10F H -0.127944 1.174677 0.916681 0.049 Uiso 1 1 calc R . . . .
C104 C -0.2151(3) 1.2247(2) 0.9731(2) 0.0533(13) Uani 1 1 d . . . . .
H10G H -0.264921 1.221948 0.938443 0.080 Uiso 1 1 calc GR . . . .
H10H H -0.178845 1.267391 0.989170 0.080 Uiso 1 1 calc GR . . . .
H10I H -0.243983 1.218212 1.004505 0.080 Uiso 1 1 calc GR . . . .
C111 C -0.3973(3) 0.88982(18) 0.8786(2) 0.0392(10) Uani 1 1 d . . . . .
H111 H -0.365990 0.887923 0.844529 0.047 Uiso 1 1 calc R . . . .
C112 C -0.4514(3) 0.94979(18) 0.8920(2) 0.0433(11) Uani 1 1 d D . . . .
H11D H -0.495730 0.948558 0.854999 0.052 Uiso 1 1 calc R . . . .
H11E H -0.488130 0.951851 0.923269 0.052 Uiso 1 1 calc R . . . .
C113 C -0.4626(3) 0.82731(19) 0.8583(2) 0.0498(12) Uani 1 1 d . . . . .
H11F H -0.511591 0.825251 0.822913 0.060 Uiso 1 1 calc R . . . .
H11G H -0.495415 0.828539 0.891188 0.060 Uiso 1 1 calc R . . . .
C114 C -0.4120(4) 0.7652(2) 0.8414(2) 0.0585(13) Uani 1 1 d . . . . .
H11H H -0.378311 0.763740 0.809294 0.088 Uiso 1 1 calc GR . . . .
H11I H -0.458893 0.727340 0.827101 0.088 Uiso 1 1 calc GR . . . .
H11J H -0.366590 0.765107 0.876908 0.088 Uiso 1 1 calc GR . . . .
C121 C -0.1926(3) 0.9680(2) 1.0835(2) 0.0454(11) Uani 1 1 d . . . . .
H121 H -0.242221 0.930144 1.065837 0.054 Uiso 1 1 calc R . . . .
C122 C -0.2405(4) 1.0260(2) 1.1140(2) 0.0544(13) Uani 1 1 d . . . . .
H12E H -0.262436 1.020088 1.148456 0.065 Uiso 1 1 calc R . . . .
H12F H -0.193688 1.064731 1.130391 0.065 Uiso 1 1 calc R . . . .
C123 C -0.1132(3) 0.9513(2) 1.1276(2) 0.0496(12) Uani 1 1 d . . . . .
H12G H -0.055453 0.981405 1.137115 0.060 Uiso 1 1 calc R . . . .
H12H H -0.134151 0.957546 1.165815 0.060 Uiso 1 1 calc R . . . .
C124 C -0.0890(3) 0.8819(2) 1.1010(2) 0.0531(13) Uani 1 1 d . . . . .
H12I H -0.069342 0.875292 1.062827 0.080 Uiso 1 1 calc GR . . . .
H12J H -0.144980 0.851890 1.093802 0.080 Uiso 1 1 calc GR . . . .
H12K H -0.037370 0.874114 1.129465 0.080 Uiso 1 1 calc GR . . . .
C130 C 1.6870(3) -0.4583(2) 0.1142(2) 0.0391(10) Uani 1 1 d . . . . .
C131 C 1.7864(3) -0.4450(2) 0.1173(2) 0.0478(12) Uani 1 1 d . . . . .
H131 H 1.814779 -0.401667 0.134005 0.057 Uiso 1 1 calc R . . . .
C132 C 1.8416(4) -0.4951(2) 0.0961(3) 0.0608(15) Uani 1 1 d . . . . .
H132 H 1.907289 -0.485462 0.099072 0.073 Uiso 1 1 calc R . . . .
C133 C 1.8006(4) -0.5604(2) 0.0701(3) 0.0733(17) Uani 1 1 d . . . . .
H133 H 1.838615 -0.593824 0.054792 0.088 Uiso 1 1 calc R . . . .
C134 C 1.7056(4) -0.5755(2) 0.0669(3) 0.0741(17) Uani 1 1 d . . . . .
H134 H 1.678949 -0.619219 0.050214 0.089 Uiso 1 1 calc R . . . .
C135 C 1.6471(4) -0.5247(2) 0.0891(2) 0.0566(13) Uani 1 1 d . . . . .
C136 C 1.5479(4) -0.5370(2) 0.0897(3) 0.0776(18) Uani 1 1 d . . . . .
H136 H 1.518253 -0.579958 0.074690 0.093 Uiso 1 1 calc R . . . .
C137 C 1.4969(4) -0.4854(2) 0.1125(3) 0.0679(16) Uani 1 1 d . . . . .
H137 H 1.431693 -0.492774 0.112166 0.081 Uiso 1 1 calc R . . . .
C138 C 1.5439(3) -0.4203(2) 0.1368(2) 0.0444(11) Uani 1 1 d . . . . .
C139 C 1.4878(3) -0.3634(2) 0.1669(2) 0.0433(11) Uani 1 1 d . . . . .
C140 C 1.1997(3) -0.49437(19) 0.2293(2) 0.0389(10) Uani 1 1 d . . . . .
C141 C 1.2826(3) -0.5004(2) 0.2040(2) 0.0510(12) Uani 1 1 d . . . . .
H141 H 1.309823 -0.464795 0.197284 0.061 Uiso 1 1 calc R . . . .
C142 C 1.3235(4) -0.5585(2) 0.1893(2) 0.0608(14) Uani 1 1 d . . . . .
H142 H 1.377969 -0.562341 0.172018 0.073 Uiso 1 1 calc R . . . .
C143 C 1.2841(4) -0.6124(2) 0.2000(2) 0.0586(14) Uani 1 1 d . . . . .
H143 H 1.312394 -0.651696 0.189284 0.070 Uiso 1 1 calc R . . . .
C144 C 1.2055(4) -0.6079(2) 0.2256(2) 0.0509(12) Uani 1 1 d . . . . .
H144 H 1.181813 -0.643603 0.233727 0.061 Uiso 1 1 calc R . . . .
C145 C 1.1588(3) -0.54931(19) 0.2402(2) 0.0409(10) Uani 1 1 d . . . . .
C146 C 1.0763(3) -0.5412(2) 0.2654(2) 0.0467(12) Uani 1 1 d . . . . .
H146 H 1.048943 -0.575415 0.274178 0.056 Uiso 1 1 calc R . . . .
C147 C 1.0358(3) -0.48333(19) 0.2772(2) 0.0438(11) Uani 1 1 d . . . . .
H147 H 0.979674 -0.477979 0.292737 0.053 Uiso 1 1 calc R . . . .
C148 C 1.0807(3) -0.43150(18) 0.2652(2) 0.0366(10) Uani 1 1 d . . . . .
C149 C 1.0403(3) -0.36451(19) 0.2835(2) 0.0400(10) Uani 1 1 d . . . . .
C150 C 0.9030(3) 0.03526(18) 0.33766(19) 0.0338(9) Uani 1 1 d . . . . .
C151 C 0.8153(3) 0.0415(2) 0.3588(2) 0.0466(12) Uani 1 1 d . . . . .
H151 H 0.775109 0.003921 0.352095 0.056 Uiso 1 1 calc R . . . .
C152 C 0.7894(3) 0.1020(2) 0.3887(2) 0.0524(12) Uani 1 1 d . . . . .
H152 H 0.731322 0.105484 0.402079 0.063 Uiso 1 1 calc R . . . .
C153 C 0.8496(4) 0.1591(2) 0.3995(2) 0.0542(13) Uani 1 1 d . . . . .
H153 H 0.831292 0.200222 0.420327 0.065 Uiso 1 1 calc R . . . .
C154 C 0.9338(4) 0.1552(2) 0.3802(2) 0.0561(13) Uani 1 1 d . . . . .
H154 H 0.972627 0.193676 0.387842 0.067 Uiso 1 1 calc R . . . .
C155 C 0.9642(3) 0.09349(19) 0.3484(2) 0.0400(10) Uani 1 1 d . . . . .
C156 C 1.0496(3) 0.0854(2) 0.3256(2) 0.0448(11) Uani 1 1 d . . . . .
H156 H 1.090615 0.122157 0.330936 0.054 Uiso 1 1 calc R . . . .
C157 C 1.0724(3) 0.0240(2) 0.2957(2) 0.0425(11) Uani 1 1 d . . . . .
H157 H 1.128587 0.018392 0.280130 0.051 Uiso 1 1 calc R . . . .
C158 C 1.0093(3) -0.03144(18) 0.28848(19) 0.0326(9) Uani 1 1 d . . . . .
C159 C 1.0357(3) -0.10015(19) 0.2563(2) 0.0357(10) Uani 1 1 d . . . . .
C160 C 0.3911(3) -0.0045(2) 0.4188(2) 0.0386(10) Uani 1 1 d . . . . .
C161 C 0.2891(3) -0.0149(2) 0.4098(2) 0.0528(12) Uani 1 1 d . . . . .
H161 H 0.255409 -0.054718 0.382619 0.063 Uiso 1 1 calc R . . . .
C162 C 0.2408(4) 0.0349(3) 0.4419(2) 0.0608(14) Uani 1 1 d . . . . .
H162 H 0.173986 0.028262 0.436373 0.073 Uiso 1 1 calc R . . . .
C163 C 0.2900(4) 0.0952(3) 0.4828(3) 0.0646(16) Uani 1 1 d . . . . .
H163 H 0.255893 0.128060 0.504539 0.078 Uiso 1 1 calc R . . . .
C164 C 0.3867(4) 0.1060(2) 0.4909(2) 0.0550(13) Uani 1 1 d . . . . .
H164 H 0.418434 0.146573 0.517849 0.066 Uiso 1 1 calc R . . . .
C165 C 0.4406(3) 0.0572(2) 0.4595(2) 0.0416(11) Uani 1 1 d . . . . .
C166 C 0.5412(4) 0.06519(19) 0.4664(2) 0.0456(12) Uani 1 1 d . . . . .
H166 H 0.576350 0.105001 0.492489 0.055 Uiso 1 1 calc R . . . .
C167 C 0.5876(3) 0.01464(19) 0.43498(19) 0.0389(10) Uani 1 1 d . . . . .
H167 H 0.654238 0.019718 0.438724 0.047 Uiso 1 1 calc R . . . .
C168 C 0.5326(3) -0.04587(18) 0.39642(18) 0.0338(9) Uani 1 1 d . . . . .
C169 C 0.5862(3) -0.10248(19) 0.36382(18) 0.0337(9) Uani 1 1 d . . . . .
C170 C 0.5951(3) 0.23131(18) 0.3612(2) 0.0353(10) Uani 1 1 d . . . . .
C171 C 0.6673(3) 0.2324(2) 0.3273(2) 0.0463(12) Uani 1 1 d . . . . .
H171 H 0.704190 0.271884 0.335795 0.056 Uiso 1 1 calc R . . . .
C172 C 0.6839(3) 0.1770(2) 0.2826(2) 0.0500(12) Uani 1 1 d . . . . .
H172 H 0.731151 0.179192 0.260607 0.060 Uiso 1 1 calc R . . . .
C173 C 0.6301(3) 0.1165(2) 0.2696(2) 0.0480(12) Uani 1 1 d . . . . .
H173 H 0.641606 0.078745 0.238975 0.058 Uiso 1 1 calc R . . . .
C174 C 0.5613(3) 0.11328(19) 0.3018(2) 0.0431(11) Uani 1 1 d . . . . .
H174 H 0.526982 0.072821 0.293327 0.052 Uiso 1 1 calc R . . . .
C175 C 0.5404(3) 0.16989(18) 0.3480(2) 0.0371(10) Uani 1 1 d . . . . .
C176 C 0.4696(3) 0.17033(19) 0.3823(2) 0.0390(10) Uani 1 1 d . . . . .
H176 H 0.433696 0.131132 0.376204 0.047 Uiso 1 1 calc R . . . .
C177 C 0.4529(3) 0.22759(19) 0.4246(2) 0.0393(10) Uani 1 1 d . . . . .
H177 H 0.404312 0.227996 0.446329 0.047 Uiso 1 1 calc R . . . .
C178 C 0.5104(3) 0.28687(18) 0.43525(19) 0.0327(9) Uani 1 1 d . . . . .
C179 C 0.4895(3) 0.35168(18) 0.47993(19) 0.0324(9) Uani 1 1 d . . . . .
C180 C -0.1272(3) 0.7209(3) 0.6857(2) 0.0517(13) Uani 1 1 d . . . . .
C181 C -0.2304(4) 0.7158(3) 0.6747(3) 0.0842(19) Uani 1 1 d . . . . .
H181 H -0.268165 0.678183 0.646111 0.101 Uiso 1 1 calc R . . . .
C182 C -0.2719(5) 0.7708(4) 0.7095(4) 0.099(3) Uani 1 1 d . . . . .
H182 H -0.338856 0.769954 0.702934 0.119 Uiso 1 1 calc R . . . .
C183 C -0.2148(7) 0.8265(4) 0.7534(4) 0.109(3) Uani 1 1 d . . . . .
H183 H -0.244457 0.861709 0.775949 0.130 Uiso 1 1 calc R . . . .
C184 C -0.1195(6) 0.8300(3) 0.7635(3) 0.085(2) Uani 1 1 d . . . . .
H184 H -0.083438 0.867529 0.793352 0.102 Uiso 1 1 calc R . . . .
C185 C -0.0708(4) 0.7783(2) 0.7301(2) 0.0561(14) Uani 1 1 d . . . . .
C186 C 0.0301(4) 0.7803(2) 0.7378(2) 0.0541(13) Uani 1 1 d . . . . .
H186 H 0.069827 0.816688 0.766775 0.065 Uiso 1 1 calc R . . . .
C187 C 0.0686(3) 0.7285(2) 0.7025(2) 0.0442(11) Uani 1 1 d . . . . .
H187 H 0.135427 0.729479 0.707207 0.053 Uiso 1 1 calc R . . . .
C188 C 0.0093(3) 0.67309(19) 0.65850(19) 0.0336(9) Uani 1 1 d . . . . .
C189 C 0.0563(3) 0.6171(2) 0.6179(2) 0.0410(10) Uani 1 1 d . . . . .
C190 C 0.1512(3) 0.76748(18) 0.8661(2) 0.0355(10) Uani 1 1 d . . . . .
C191 C 0.2459(3) 0.7819(2) 0.8592(2) 0.0472(12) Uani 1 1 d . . . . .
H191 H 0.271580 0.825487 0.871175 0.057 Uiso 1 1 calc R . . . .
C192 C 0.2990(4) 0.7322(2) 0.8352(3) 0.0669(16) Uani 1 1 d . . . . .
H192 H 0.360421 0.742138 0.829953 0.080 Uiso 1 1 calc R . . . .
C193 C 0.2628(4) 0.6660(2) 0.8181(3) 0.0759(18) Uani 1 1 d . . . . .
H193 H 0.300028 0.632370 0.801876 0.091 Uiso 1 1 calc R . . . .
C194 C 0.1729(3) 0.6516(2) 0.8256(3) 0.0619(15) Uani 1 1 d . . . . .
H194 H 0.148947 0.607710 0.814177 0.074 Uiso 1 1 calc R . . . .
C195 C 0.1152(3) 0.70138(19) 0.8502(2) 0.0433(11) Uani 1 1 d . . . . .
C196 C 0.0215(3) 0.6895(2) 0.8593(2) 0.0473(12) Uani 1 1 d . . . . .
H196 H -0.004330 0.646572 0.850635 0.057 Uiso 1 1 calc R . . . .
C197 C -0.0307(3) 0.74062(19) 0.8806(2) 0.0421(11) Uani 1 1 d . . . . .
H197 H -0.092757 0.733094 0.886198 0.051 Uiso 1 1 calc R . . . .
C198 C 0.0104(3) 0.80564(18) 0.89409(18) 0.0329(9) Uani 1 1 d . . . . .
C199 C -0.0478(3) 0.86311(19) 0.91894(18) 0.0339(9) Uani 1 1 d . . . . .
C200 C -0.6742(3) 1.25740(18) 1.00253(19) 0.0337(9) Uani 1 1 d . . . . .
C201 C -0.7631(3) 1.2656(2) 1.0215(2) 0.0438(11) Uani 1 1 d . . . . .
H201 H -0.791852 1.232529 1.031195 0.053 Uiso 1 1 calc R . . . .
C202 C -0.8072(4) 1.3210(2) 1.0260(2) 0.0552(13) Uani 1 1 d . . . . .
H202 H -0.866505 1.325394 1.037842 0.066 Uiso 1 1 calc R . . . .
C203 C -0.7633(4) 1.3722(2) 1.0125(2) 0.0572(14) Uani 1 1 d . . . . .
H203 H -0.793584 1.410350 1.016304 0.069 Uiso 1 1 calc R . . . .
C204 C -0.6787(3) 1.3664(2) 0.9945(2) 0.0494(12) Uani 1 1 d . . . . .
H204 H -0.651434 1.400330 0.985265 0.059 Uiso 1 1 calc R . . . .
C205 C -0.6299(3) 1.30916(18) 0.98917(19) 0.0371(10) Uani 1 1 d . . . . .
C206 C -0.5410(3) 1.29945(18) 0.97044(19) 0.0399(11) Uani 1 1 d . . . . .
H206 H -0.509916 1.332012 0.961301 0.048 Uiso 1 1 calc R . . . .
C207 C -0.5006(3) 1.24231(18) 0.96568(19) 0.0374(10) Uani 1 1 d . . . . .
H207 H -0.440810 1.236014 0.954704 0.045 Uiso 1 1 calc R . . . .
C208 C -0.5515(3) 1.19264(17) 0.97782(18) 0.0317(9) Uani 1 1 d . . . . .
C209 C -0.5130(3) 1.12546(18) 0.9654(2) 0.0354(10) Uani 1 1 d . . . . .
C71 C 0.3874(5) 0.5587(3) 0.6490(3) 0.0530(8) Uani 0.733(4) 1 d D . P B 1
H71 H 0.344092 0.541685 0.669290 0.064 Uiso 0.733(4) 1 calc R . P B 1
C73 C 0.4569(4) 0.6164(3) 0.6969(3) 0.0530(8) Uani 0.733(4) 1 d D . P B 1
H73A H 0.422652 0.655438 0.706937 0.064 Uiso 0.733(4) 1 calc R . P B 1
H73B H 0.475426 0.606703 0.734212 0.064 Uiso 0.733(4) 1 calc R . P B 1
C74 C 0.5482(4) 0.6320(3) 0.6771(3) 0.0530(8) Uani 0.733(4) 1 d D . P B 1
H74A H 0.531071 0.638288 0.638469 0.080 Uiso 0.733(4) 1 calc GR . P B 1
H74B H 0.587393 0.596052 0.672594 0.080 Uiso 0.733(4) 1 calc GR . P B 1
H74C H 0.583854 0.671457 0.707785 0.080 Uiso 0.733(4) 1 calc GR . P B 1
C71A C 0.4129(11) 0.5721(7) 0.6398(7) 0.0530(8) Uani 0.267(4) 1 d D . P B 2
H71A H 0.464803 0.606651 0.647117 0.064 Uiso 0.267(4) 1 calc R . P B 2
C73A C 0.3744(11) 0.5804(8) 0.6944(7) 0.0530(8) Uani 0.267(4) 1 d D . P B 2
H73C H 0.322418 0.545972 0.685144 0.064 Uiso 0.267(4) 1 calc R . P B 2
H73D H 0.348619 0.622664 0.707836 0.064 Uiso 0.267(4) 1 calc R . P B 2
C74A C 0.4561(11) 0.5768(8) 0.7455(8) 0.0530(8) Uani 0.267(4) 1 d D . P B 2
H74D H 0.489539 0.538926 0.729348 0.080 Uiso 0.267(4) 1 calc GR . P B 2
H74E H 0.429175 0.573199 0.778782 0.080 Uiso 0.267(4) 1 calc GR . P B 2
H74F H 0.500587 0.615958 0.760465 0.080 Uiso 0.267(4) 1 calc GR . P B 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 O1 2.355(3) . ?
Cu1 O2 2.005(3) . ?
Cu1 N1 2.009(3) . ?
Cu1 N2 1.998(3) . ?
Cu1 N3 2.019(3) . ?
Cu2 O4 1.997(3) . ?
Cu2 O5 2.381(3) . ?
Cu2 N4 2.010(3) . ?
Cu2 N5 1.991(3) . ?
Cu2 N6 2.004(3) . ?
Cu3 O7 2.015(3) . ?
Cu3 O8 2.389(3) . ?
Cu3 N7 2.004(3) . ?
Cu3 N8 2.011(3) . ?
Cu3 N9 2.019(3) . ?
Cu4 O10 2.331(3) . ?
Cu4 O11 1.995(3) . ?
Cu4 N10 1.997(3) . ?
Cu4 N11 2.000(3) . ?
Cu4 N12 2.020(3) . ?
O1 C12 1.435(4) . ?
O2 C22 1.434(4) . ?
O3 C32 1.422(5) . ?
O4 C42 1.424(5) . ?
O5 C52 1.459(5) . ?
O6 C62 1.407(5) . ?
O7 C72 1.419(5) . ?
O8 C82 1.425(4) . ?
O9 C92 1.422(5) . ?
O10 C102 1.443(4) . ?
O11 C112 1.430(4) . ?
O12 C122 1.448(5) . ?
O13 C139 1.255(4) . ?
O14 C149 1.245(4) . ?
O15 C159 1.240(4) . ?
O16 C169 1.263(4) . ?
O17 C179 1.240(4) . ?
O18 C189 1.253(5) . ?
O19 C199 1.257(4) . ?
O20 C209 1.238(4) . ?
O131 C139 1.249(5) . ?
O141 C149 1.254(5) . ?
O151 C159 1.267(4) . ?
O161 C169 1.254(4) . ?
O171 C179 1.261(4) . ?
O181 C189 1.238(5) . ?
O191 C199 1.252(4) . ?
O201 C209 1.257(4) . ?
N1 C11 1.489(4) . ?
N2 C21 1.476(5) . ?
N3 C31 1.492(5) . ?
N4 C41 1.477(6) . ?
N5 C51 1.466(5) . ?
N6 C61 1.487(5) . ?
N7 C71 1.527(7) . ?
N7 C71A 1.449(14) . ?
N8 C81 1.477(5) . ?
N9 C91 1.487(5) . ?
N10 C101 1.497(5) . ?
N11 C111 1.481(5) . ?
N12 C121 1.499(5) . ?
N13 C130 1.354(5) . ?
N13 C138 1.316(5) . ?
N14 C140 1.365(5) . ?
N14 C148 1.315(5) . ?
N15 C150 1.366(5) . ?
N15 C158 1.313(5) . ?
N16 C160 1.374(5) . ?
N16 C168 1.304(5) . ?
N17 C170 1.366(5) . ?
N17 C178 1.324(5) . ?
N18 C180 1.381(5) . ?
N18 C188 1.334(5) . ?
N19 C190 1.367(5) . ?
N19 C198 1.317(4) . ?
N20 C200 1.368(5) . ?
N20 C208 1.313(5) . ?
C11 C12 1.508(5) . ?
C11 C13 1.523(5) . ?
C13 C14 1.520(5) . ?
C21 C22 1.513(5) . ?
C21 C23 1.519(5) . ?
C23 C24 1.542(6) . ?
C31 C32 1.483(6) . ?
C31 C33 1.523(6) . ?
C33 C34 1.513(6) . ?
C41 C42 1.459(7) . ?
C41 C43 1.511(7) . ?
C43 C44 1.488(9) . ?
C51 C52 1.494(6) . ?
C51 C53 1.529(5) . ?
C53 C54 1.530(6) . ?
C61 C62 1.524(6) . ?
C61 C63 1.459(6) . ?
C63 C64 1.516(6) . ?
C72 C71 1.526(7) . ?
C72 C71A 1.505(14) . ?
C81 C82 1.500(6) . ?
C81 C83 1.519(5) . ?
C83 C84 1.513(6) . ?
C91 C92 1.509(6) . ?
C91 C93 1.342(8) . ?
C93 C94 1.447(8) . ?
C101 C102 1.500(5) . ?
C101 C103 1.535(5) . ?
C103 C104 1.516(6) . ?
C111 C112 1.501(5) . ?
C111 C113 1.495(5) . ?
C113 C114 1.514(6) . ?
C121 C122 1.476(6) . ?
C121 C123 1.529(6) . ?
C123 C124 1.498(6) . ?
C130 C131 1.411(6) . ?
C130 C135 1.409(6) . ?
C131 C132 1.367(6) . ?
C132 C133 1.393(6) . ?
C133 C134 1.355(7) . ?
C134 C135 1.412(6) . ?
C135 C136 1.425(7) . ?
C136 C137 1.358(7) . ?
C137 C138 1.419(6) . ?
C138 C139 1.525(6) . ?
C140 C141 1.403(6) . ?
C140 C145 1.434(5) . ?
C141 C142 1.368(6) . ?
C142 C143 1.401(6) . ?
C143 C144 1.353(6) . ?
C144 C145 1.418(6) . ?
C145 C146 1.395(6) . ?
C146 C147 1.362(6) . ?
C147 C148 1.414(5) . ?
C148 C149 1.531(5) . ?
C150 C151 1.414(5) . ?
C150 C155 1.430(5) . ?
C151 C152 1.358(6) . ?
C152 C153 1.403(6) . ?
C153 C154 1.347(6) . ?
C154 C155 1.416(6) . ?
C155 C156 1.404(6) . ?
C156 C157 1.357(6) . ?
C157 C158 1.420(5) . ?
C158 C159 1.518(5) . ?
C160 C161 1.418(6) . ?
C160 C165 1.420(6) . ?
C161 C162 1.371(6) . ?
C162 C163 1.398(7) . ?
C163 C164 1.347(7) . ?
C164 C165 1.404(6) . ?
C165 C166 1.401(6) . ?
C166 C167 1.360(6) . ?
C167 C168 1.417(5) . ?
C168 C169 1.518(5) . ?
C170 C171 1.414(5) . ?
C170 C175 1.427(5) . ?
C171 C172 1.359(6) . ?
C172 C173 1.405(5) . ?
C173 C174 1.356(6) . ?
C174 C175 1.416(6) . ?
C175 C176 1.402(5) . ?
C176 C177 1.359(6) . ?
C177 C178 1.422(5) . ?
C178 C179 1.516(5) . ?
C180 C181 1.428(7) . ?
C180 C185 1.419(7) . ?
C181 C182 1.413(8) . ?
C182 C183 1.397(10) . ?
C183 C184 1.320(9) . ?
C184 C185 1.414(7) . ?
C185 C186 1.403(7) . ?
C186 C187 1.347(6) . ?
C187 C188 1.407(5) . ?
C188 C189 1.525(6) . ?
C190 C191 1.417(5) . ?
C190 C195 1.406(5) . ?
C191 C192 1.356(6) . ?
C192 C193 1.404(6) . ?
C193 C194 1.358(6) . ?
C194 C195 1.405(6) . ?
C195 C196 1.410(6) . ?
C196 C197 1.356(6) . ?
C197 C198 1.416(5) . ?
C198 C199 1.524(5) . ?
C200 C201 1.409(5) . ?
C200 C205 1.427(5) . ?
C201 C202 1.357(6) . ?
C202 C203 1.416(6) . ?
C203 C204 1.340(6) . ?
C204 C205 1.423(5) . ?
C205 C206 1.407(5) . ?
C206 C207 1.363(5) . ?
C207 C208 1.419(5) . ?
C208 C209 1.527(5) . ?
C71 C73 1.532(7) . ?
C73 C74 1.520(8) . ?
C71A C73A 1.450(16) . ?
C73A C74A 1.537(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O1 96.83(10) . . ?
O2 Cu1 N1 87.31(11) . . ?
O2 Cu1 N3 169.96(10) . . ?
N1 Cu1 O1 79.28(10) . . ?
N1 Cu1 N3 98.27(12) . . ?
N2 Cu1 O1 96.52(11) . . ?
N2 Cu1 O2 82.58(12) . . ?
N2 Cu1 N1 168.55(13) . . ?
N2 Cu1 N3 92.53(13) . . ?
N3 Cu1 O1 92.42(11) . . ?
O4 Cu2 O5 93.55(12) . . ?
O4 Cu2 N4 82.18(14) . . ?
O4 Cu2 N6 173.80(12) . . ?
N4 Cu2 O5 98.48(12) . . ?
N5 Cu2 O4 87.25(13) . . ?
N5 Cu2 O5 79.26(11) . . ?
N5 Cu2 N4 169.05(15) . . ?
N5 Cu2 N6 97.55(14) . . ?
N6 Cu2 O5 91.21(11) . . ?
N6 Cu2 N4 93.20(14) . . ?
O7 Cu3 O8 96.88(11) . . ?
O7 Cu3 N9 172.78(12) . . ?
N7 Cu3 O7 82.46(13) . . ?
N7 Cu3 O8 95.11(12) . . ?
N7 Cu3 N8 166.75(14) . . ?
N7 Cu3 N9 93.22(14) . . ?
N8 Cu3 O7 87.00(12) . . ?
N8 Cu3 O8 78.16(11) . . ?
N8 Cu3 N9 98.04(14) . . ?
N9 Cu3 O8 89.24(12) . . ?
O11 Cu4 O10 93.29(11) . . ?
O11 Cu4 N10 87.30(12) . . ?
O11 Cu4 N11 82.78(11) . . ?
O11 Cu4 N12 172.24(11) . . ?
N10 Cu4 O10 80.26(11) . . ?
N10 Cu4 N11 169.23(13) . . ?
N10 Cu4 N12 97.51(13) . . ?
N11 Cu4 O10 96.09(11) . . ?
N11 Cu4 N12 92.81(12) . . ?
N12 Cu4 O10 93.53(11) . . ?
C12 O1 Cu1 105.4(2) . . ?
C22 O2 Cu1 111.8(2) . . ?
C42 O4 Cu2 111.3(3) . . ?
C52 O5 Cu2 103.8(2) . . ?
C72 O7 Cu3 110.9(2) . . ?
C82 O8 Cu3 105.3(2) . . ?
C102 O10 Cu4 104.9(2) . . ?
C112 O11 Cu4 111.7(2) . . ?
C11 N1 Cu1 110.1(2) . . ?
C21 N2 Cu1 109.7(2) . . ?
C31 N3 Cu1 111.8(2) . . ?
C41 N4 Cu2 110.4(3) . . ?
C51 N5 Cu2 111.7(3) . . ?
C61 N6 Cu2 110.7(3) . . ?
C71 N7 Cu3 105.9(3) . . ?
C71A N7 Cu3 116.6(6) . . ?
C81 N8 Cu3 110.6(2) . . ?
C91 N9 Cu3 111.5(3) . . ?
C101 N10 Cu4 110.6(2) . . ?
C111 N11 Cu4 109.7(2) . . ?
C121 N12 Cu4 113.8(2) . . ?
C138 N13 C130 118.5(3) . . ?
C148 N14 C140 118.2(3) . . ?
C158 N15 C150 119.0(3) . . ?
C168 N16 C160 118.1(4) . . ?
C178 N17 C170 118.9(3) . . ?
C188 N18 C180 116.8(4) . . ?
C198 N19 C190 118.2(3) . . ?
C208 N20 C200 118.3(3) . . ?
N1 C11 C12 109.0(3) . . ?
N1 C11 C13 113.9(3) . . ?
C12 C11 C13 110.7(3) . . ?
O1 C12 C11 108.8(3) . . ?
C14 C13 C11 113.9(3) . . ?
N2 C21 C22 107.2(3) . . ?
N2 C21 C23 114.3(3) . . ?
C22 C21 C23 110.5(3) . . ?
O2 C22 C21 106.1(3) . . ?
C21 C23 C24 113.7(4) . . ?
N3 C31 C33 112.6(4) . . ?
C32 C31 N3 109.2(3) . . ?
C32 C31 C33 113.5(4) . . ?
O3 C32 C31 112.8(4) . . ?
C34 C33 C31 112.6(4) . . ?
N4 C41 C43 115.5(4) . . ?
C42 C41 N4 107.9(5) . . ?
C42 C41 C43 111.6(5) . . ?
O4 C42 C41 109.4(4) . . ?
C44 C43 C41 116.1(5) . . ?
N5 C51 C52 109.8(3) . . ?
N5 C51 C53 114.1(4) . . ?
C52 C51 C53 111.1(3) . . ?
O5 C52 C51 110.4(3) . . ?
C51 C53 C54 113.4(4) . . ?
N6 C61 C62 107.4(3) . . ?
C63 C61 N6 114.9(4) . . ?
C63 C61 C62 114.8(4) . . ?
O6 C62 C61 110.5(4) . . ?
C61 C63 C64 116.5(4) . . ?
O7 C72 C71 103.6(4) . . ?
O7 C72 C71A 116.6(7) . . ?
N8 C81 C82 109.5(3) . . ?
N8 C81 C83 114.5(4) . . ?
C82 C81 C83 111.1(3) . . ?
O8 C82 C81 109.1(3) . . ?
C84 C83 C81 113.7(4) . . ?
N9 C91 C92 107.6(4) . . ?
C93 C91 N9 121.5(5) . . ?
C93 C91 C92 120.8(5) . . ?
O9 C92 C91 110.9(4) . . ?
C91 C93 C94 125.9(8) . . ?
N10 C101 C102 108.9(3) . . ?
N10 C101 C103 113.7(3) . . ?
C102 C101 C103 111.0(3) . . ?
O10 C102 C101 110.4(3) . . ?
C104 C103 C101 115.1(3) . . ?
N11 C111 C112 107.6(3) . . ?
N11 C111 C113 114.5(3) . . ?
C113 C111 C112 112.5(3) . . ?
O11 C112 C111 106.7(3) . . ?
C111 C113 C114 114.5(4) . . ?
N12 C121 C123 113.2(3) . . ?
C122 C121 N12 108.6(3) . . ?
C122 C121 C123 113.6(4) . . ?
O12 C122 C121 113.2(4) . . ?
C124 C123 C121 112.2(4) . . ?
N13 C130 C131 118.8(4) . . ?
N13 C130 C135 123.5(4) . . ?
C135 C130 C131 117.7(4) . . ?
C132 C131 C130 120.9(4) . . ?
C131 C132 C133 120.7(4) . . ?
C134 C133 C132 120.5(5) . . ?
C133 C134 C135 120.0(5) . . ?
C130 C135 C134 120.3(4) . . ?
C130 C135 C136 116.5(4) . . ?
C134 C135 C136 123.1(5) . . ?
C137 C136 C135 119.5(4) . . ?
C136 C137 C138 119.6(5) . . ?
N13 C138 C137 122.5(4) . . ?
N13 C138 C139 118.5(4) . . ?
C137 C138 C139 118.9(4) . . ?
O13 C139 C138 117.8(4) . . ?
O131 C139 O13 125.6(4) . . ?
O131 C139 C138 116.6(4) . . ?
N14 C140 C141 118.8(3) . . ?
N14 C140 C145 121.7(4) . . ?
C141 C140 C145 119.5(4) . . ?
C142 C141 C140 120.2(4) . . ?
C141 C142 C143 120.6(5) . . ?
C144 C143 C142 120.9(4) . . ?
C143 C144 C145 120.7(4) . . ?
C144 C145 C140 118.1(4) . . ?
C146 C145 C140 117.6(4) . . ?
C146 C145 C144 124.3(4) . . ?
C147 C146 C145 120.0(4) . . ?
C146 C147 C148 118.7(4) . . ?
N14 C148 C147 123.7(4) . . ?
N14 C148 C149 117.4(3) . . ?
C147 C148 C149 118.8(4) . . ?
O14 C149 O141 126.9(4) . . ?
O14 C149 C148 117.9(4) . . ?
O141 C149 C148 115.2(3) . . ?
N15 C150 C151 119.5(3) . . ?
N15 C150 C155 121.5(4) . . ?
C151 C150 C155 119.1(4) . . ?
C152 C151 C150 120.5(4) . . ?
C151 C152 C153 120.4(4) . . ?
C154 C153 C152 120.8(4) . . ?
C153 C154 C155 121.3(4) . . ?
C154 C155 C150 117.9(4) . . ?
C156 C155 C150 117.4(4) . . ?
C156 C155 C154 124.6(4) . . ?
C157 C156 C155 120.1(4) . . ?
C156 C157 C158 119.0(4) . . ?
N15 C158 C157 122.8(4) . . ?
N15 C158 C159 118.0(3) . . ?
C157 C158 C159 119.1(4) . . ?
O15 C159 O151 125.3(4) . . ?
O15 C159 C158 118.1(4) . . ?
O151 C159 C158 116.6(3) . . ?
N16 C160 C161 118.3(4) . . ?
N16 C160 C165 122.1(4) . . ?
C161 C160 C165 119.5(4) . . ?
C162 C161 C160 118.9(5) . . ?
C161 C162 C163 121.4(5) . . ?
C164 C163 C162 120.1(5) . . ?
C163 C164 C165 121.5(5) . . ?
C164 C165 C160 118.5(4) . . ?
C166 C165 C160 117.4(4) . . ?
C166 C165 C164 124.1(5) . . ?
C167 C166 C165 120.0(4) . . ?
C166 C167 C168 118.9(4) . . ?
N16 C168 C167 123.5(4) . . ?
N16 C168 C169 118.5(4) . . ?
C167 C168 C169 118.0(4) . . ?
O16 C169 C168 118.4(3) . . ?
O161 C169 O16 124.7(4) . . ?
O161 C169 C168 116.9(3) . . ?
N17 C170 C171 119.6(3) . . ?
N17 C170 C175 122.3(4) . . ?
C171 C170 C175 118.2(4) . . ?
C172 C171 C170 121.6(4) . . ?
C171 C172 C173 120.3(4) . . ?
C174 C173 C172 119.9(4) . . ?
C173 C174 C175 121.7(4) . . ?
C174 C175 C170 118.3(4) . . ?
C176 C175 C170 116.9(4) . . ?
C176 C175 C174 124.8(4) . . ?
C177 C176 C175 120.5(3) . . ?
C176 C177 C178 119.3(4) . . ?
N17 C178 C177 122.1(4) . . ?
N17 C178 C179 117.9(3) . . ?
C177 C178 C179 119.9(4) . . ?
O17 C179 O171 125.8(4) . . ?
O17 C179 C178 118.5(3) . . ?
O171 C179 C178 115.7(3) . . ?
N18 C180 C181 116.2(5) . . ?
N18 C180 C185 122.8(4) . . ?
C185 C180 C181 120.9(5) . . ?
C182 C181 C180 116.4(7) . . ?
C183 C182 C181 121.6(7) . . ?
C184 C183 C182 121.0(7) . . ?
C183 C184 C185 121.8(7) . . ?
C184 C185 C180 118.2(6) . . ?
C186 C185 C180 117.7(4) . . ?
C186 C185 C184 124.1(6) . . ?
C187 C186 C185 118.9(5) . . ?
C186 C187 C188 121.1(4) . . ?
N18 C188 C187 122.6(4) . . ?
N18 C188 C189 118.3(4) . . ?
C187 C188 C189 119.0(4) . . ?
O18 C189 C188 117.9(4) . . ?
O181 C189 O18 126.4(4) . . ?
O181 C189 C188 115.7(4) . . ?
N19 C190 C191 118.1(3) . . ?
N19 C190 C195 122.7(4) . . ?
C195 C190 C191 119.1(4) . . ?
C192 C191 C190 120.1(4) . . ?
C191 C192 C193 121.2(4) . . ?
C194 C193 C192 119.3(5) . . ?
C193 C194 C195 121.6(4) . . ?
C190 C195 C196 117.1(4) . . ?
C194 C195 C190 118.7(4) . . ?
C194 C195 C196 124.1(4) . . ?
C197 C196 C195 120.0(4) . . ?
C196 C197 C198 119.1(4) . . ?
N19 C198 C197 122.8(4) . . ?
N19 C198 C199 118.2(3) . . ?
C197 C198 C199 119.0(3) . . ?
O19 C199 C198 117.8(3) . . ?
O191 C199 O19 125.7(4) . . ?
O191 C199 C198 116.5(3) . . ?
N20 C200 C201 119.1(3) . . ?
N20 C200 C205 122.0(4) . . ?
C201 C200 C205 118.9(3) . . ?
C202 C201 C200 120.8(4) . . ?
C201 C202 C203 120.2(4) . . ?
C204 C203 C202 120.8(4) . . ?
C203 C204 C205 120.9(4) . . ?
C204 C205 C200 118.3(4) . . ?
C206 C205 C200 117.4(3) . . ?
C206 C205 C204 124.2(4) . . ?
C207 C206 C205 120.0(3) . . ?
C206 C207 C208 118.6(4) . . ?
N20 C208 C207 123.6(3) . . ?
N20 C208 C209 117.1(3) . . ?
C207 C208 C209 119.1(3) . . ?
O20 C209 O201 125.6(4) . . ?
O20 C209 C208 118.3(4) . . ?
O201 C209 C208 116.1(3) . . ?
N7 C71 C73 114.3(5) . . ?
C72 C71 N7 102.6(5) . . ?
C72 C71 C73 110.1(5) . . ?
C74 C73 C71 115.1(5) . . ?
N7 C71A C72 107.5(9) . . ?
N7 C71A C73A 102.1(11) . . ?
C73A C71A C72 109.7(13) . . ?
C71A C73A C74A 108.8(13) . . ?

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
_geom_hbond_publ_flag
O1 H1 O13 0.863(9) 1.96(3) 2.685(4) 140(3) . yes
O2 H2 O151 0.868(9) 1.713(17) 2.508(4) 151(3) . yes
O3 H3 O14 0.82 1.97 2.760(4) 162.4 . yes
O4 H4 O141 0.870(9) 1.661(16) 2.490(4) 158(3) . yes
O5 H5 O16 0.874(9) 1.99(3) 2.723(4) 140(3) . yes
O6 H6 O15 0.82 1.94 2.742(4) 165.0 . yes
O7 H7 O171 0.871(9) 1.716(17) 2.518(4) 152(3) . yes
O8 H8 O18 0.877(9) 1.94(2) 2.729(4) 148(3) . yes
O9 H9 O17 0.82 1.96 2.757(4) 162.4 2_666 yes
O10 H10 O19 0.860(9) 2.00(3) 2.695(4) 138(3) . yes
O11 H11A O201 0.874(9) 1.686(13) 2.521(4) 159(2) . yes
O12 H12 O20 0.82 1.95 2.761(4) 169.7 2_477 yes
N1 H1A O151 0.89 2.31 3.063(4) 142.1 . yes
N1 H1B N16 0.89 2.28 3.091(5) 151.6 1_655 yes
N2 H2A O131 0.89 2.17 3.007(4) 155.7 . yes
N2 H2B O14 0.89 2.29 3.061(4) 144.7 . yes
N3 H3B O16 0.89 2.12 2.998(4) 170.0 1_655 yes
N4 H4A O15 0.89 2.28 3.051(4) 145.2 . yes
N4 H4B O161 0.89 2.21 3.019(5) 151.0 . yes
N6 H6B O161 0.89 2.16 2.986(4) 154.4 . yes
N7 H7B O181 0.89 2.18 3.014(5) 155.6 . yes
N9 H9A O18 0.89 2.15 3.035(5) 175.1 2_566 yes
N10 H10B N19 0.89 2.24 3.039(4) 149.7 2_577 yes
N11 H11B O191 0.89 2.17 2.996(4) 153.3 . yes
N11 H11C O20 0.89 2.20 2.967(4) 144.5 2_477 yes
N12 H12C O191 0.89 2.23 3.056(4) 154.4 . yes
N12 H12D O19 0.89 2.15 3.035(4) 169.8 2_577 yes

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.470
_oxdiff_exptl_absorpt_empirical_full_min 0.706
####################################################################### 
# 
# 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_syn-11d
_database_code_depnum_ccdc_archive 'CCDC 2077011'
loop_
_audit_author_name
_audit_author_address
'Barbara Modec'
;University of Ljubljana
Slovenia
;
_audit_update_record             
;
2021-04-12 deposited with the CCDC.	2022-03-18 downloaded from the CCDC.
;
_audit_creation_date             2021-03-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H28 Cu2 N4 O6'
_chemical_formula_sum            'C26 H28 Cu2 N4 O6'
_chemical_formula_weight         619.60
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.5521(5)
_cell_length_b                   10.1620(5)
_cell_length_c                   14.8273(10)
_cell_angle_alpha                72.689(5)
_cell_angle_beta                 75.638(5)
_cell_angle_gamma                66.350(5)
_cell_volume                     1244.97(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4675
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      29.6770
_cell_measurement_theta_min      3.2180
_shelx_estimated_absorpt_T_max   0.917
_shelx_estimated_absorpt_T_min   0.844
_exptl_absorpt_coefficient_mu    1.759
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.74554
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.653
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             636
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.856
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            11625
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.856
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.270
_diffrn_reflns_theta_min         2.353
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.856
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -38.00  38.00   1.00   25.00    --   14.05 -77.00 120.00   76
  2  ω     44.00  70.00   1.00   25.00    --   14.05 178.00-120.00   26
  3  ω    -41.00  51.00   1.00   25.00    --  -14.36  57.00  30.00   92
  4  ω    -36.00  16.00   1.00   25.00    --  -14.36 -77.00 120.00   52
  5  ω    -88.00  10.00   1.00   25.00    --  -14.36 -57.00-120.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0285557000
_diffrn_orient_matrix_UB_12      0.0781266000
_diffrn_orient_matrix_UB_13      -0.0097880000
_diffrn_orient_matrix_UB_21      -0.0118228000
_diffrn_orient_matrix_UB_22      0.0026210000
_diffrn_orient_matrix_UB_23      -0.0459740000
_diffrn_orient_matrix_UB_31      -0.0759060000
_diffrn_orient_matrix_UB_32      0.0000732000
_diffrn_orient_matrix_UB_33      0.0188917000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5071
_reflns_number_total             6377
_reflns_odcompleteness_completeness 99.86
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.409
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     359
_refine_ls_number_reflns         6377
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0487
_refine_ls_R_factor_gt           0.0337
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0311P)²+0.3674P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0745
_refine_ls_wR_factor_ref         0.0827
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C31(H31A,H31B), C32(H32A,H32B), C33(H33A,H33B), C41(H41A,H41B), C42(H42A,
 H42B), C43(H43A,H43B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17), C21(H21),
 C22(H22), C23(H23), C24(H24), C26(H26), C27(H27)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.76559(3) 0.55271(3) 0.62874(2) 0.01581(7) Uani 1 1 d . . . . .
Cu2 Cu 0.43461(3) 0.57540(3) 0.63564(2) 0.01917(8) Uani 1 1 d . . . . .
O1 O 0.89186(17) 0.65501(16) 0.53044(12) 0.0200(3) Uani 1 1 d . . . . .
O2 O 0.31369(18) 0.44625(18) 0.69840(14) 0.0275(4) Uani 1 1 d . . . . .
O3 O 0.61518(17) 0.46416(16) 0.70248(12) 0.0191(3) Uani 1 1 d . . . . .
O4 O 0.58182(17) 0.66833(17) 0.56804(12) 0.0221(4) Uani 1 1 d . . . . .
O11 O 0.9890(2) 0.83377(19) 0.48726(14) 0.0316(4) Uani 1 1 d . . . . .
O22 O 0.1232(2) 0.40592(19) 0.81173(15) 0.0332(4) Uani 1 1 d . . . . .
N1 N 0.7780(2) 0.71409(18) 0.70545(14) 0.0166(4) Uani 1 1 d . . . . .
N2 N 0.2798(2) 0.68445(19) 0.75932(14) 0.0192(4) Uani 1 1 d . . . . .
N3 N 0.9511(2) 0.3828(2) 0.66896(17) 0.0208(4) Uani 1 1 d . . . . .
H3A H 0.995(3) 0.404(3) 0.699(2) 0.036(8) Uiso 1 1 d . . . . .
H3B H 1.008(3) 0.364(3) 0.622(2) 0.025(8) Uiso 1 1 d . . . . .
N4 N 0.3130(3) 0.6512(3) 0.5269(2) 0.0323(6) Uani 1 1 d . . . . .
H4A H 0.237(4) 0.695(4) 0.550(3) 0.048(11) Uiso 1 1 d . . . . .
H4B H 0.321(4) 0.566(4) 0.512(3) 0.062(10) Uiso 1 1 d . . . . .
C10 C 0.7252(2) 0.7366(2) 0.79589(17) 0.0168(4) Uani 1 1 d . . . . .
C11 C 0.6277(3) 0.6635(2) 0.85868(18) 0.0217(5) Uani 1 1 d . . . . .
H11 H 0.600155 0.600416 0.838110 0.026 Uiso 1 1 calc R . . . .
C12 C 0.5738(3) 0.6852(3) 0.94942(19) 0.0256(5) Uani 1 1 d . . . . .
H12 H 0.510322 0.635999 0.990268 0.031 Uiso 1 1 calc R . . . .
C13 C 0.6130(3) 0.7812(3) 0.9820(2) 0.0299(6) Uani 1 1 d . . . . .
H13 H 0.575961 0.794619 1.044083 0.036 Uiso 1 1 calc R . . . .
C14 C 0.7053(3) 0.8544(3) 0.92242(19) 0.0275(5) Uani 1 1 d . . . . .
H14 H 0.729568 0.918463 0.944182 0.033 Uiso 1 1 calc R . . . .
C15 C 0.7646(3) 0.8346(2) 0.82840(18) 0.0205(5) Uani 1 1 d . . . . .
C16 C 0.8608(3) 0.9067(2) 0.76310(19) 0.0231(5) Uani 1 1 d . . . . .
H16 H 0.890807 0.969451 0.782276 0.028 Uiso 1 1 calc R . . . .
C17 C 0.9100(3) 0.8855(2) 0.67270(18) 0.0207(5) Uani 1 1 d . . . . .
H17 H 0.971193 0.934788 0.629171 0.025 Uiso 1 1 calc R . . . .
C18 C 0.8657(2) 0.7862(2) 0.64638(17) 0.0165(4) Uani 1 1 d . . . . .
C19 C 0.9194(2) 0.7589(2) 0.54623(18) 0.0185(5) Uani 1 1 d . . . . .
C20 C 0.2717(2) 0.7990(2) 0.79419(17) 0.0193(5) Uani 1 1 d . . . . .
C21 C 0.3458(3) 0.8977(2) 0.73579(18) 0.0232(5) Uani 1 1 d . . . . .
H21 H 0.398604 0.884282 0.675548 0.028 Uiso 1 1 calc R . . . .
C22 C 0.3392(3) 1.0137(2) 0.76860(19) 0.0255(5) Uani 1 1 d . . . . .
H22 H 0.387518 1.078618 0.729961 0.031 Uiso 1 1 calc R . . . .
C23 C 0.2609(3) 1.0354(3) 0.85909(19) 0.0273(5) Uani 1 1 d . . . . .
H23 H 0.256734 1.114838 0.879895 0.033 Uiso 1 1 calc R . . . .
C24 C 0.1902(3) 0.9400(3) 0.91722(19) 0.0268(5) Uani 1 1 d . . . . .
H24 H 0.140037 0.954161 0.977794 0.032 Uiso 1 1 calc R . . . .
C25 C 0.1929(2) 0.8196(2) 0.88582(18) 0.0212(5) Uani 1 1 d . . . . .
C26 C 0.1214(3) 0.7180(3) 0.94260(19) 0.0282(5) Uani 1 1 d . . . . .
H26 H 0.070376 0.727105 1.003842 0.034 Uiso 1 1 calc R . . . .
C27 C 0.1283(3) 0.6069(3) 0.90637(19) 0.0279(5) Uani 1 1 d . . . . .
H27 H 0.080555 0.540073 0.942284 0.033 Uiso 1 1 calc R . . . .
C28 C 0.2078(2) 0.5940(2) 0.81456(18) 0.0208(5) Uani 1 1 d . . . . .
C29 C 0.2147(3) 0.4709(2) 0.77214(19) 0.0235(5) Uani 1 1 d . . . . .
C31 C 0.9240(3) 0.2470(2) 0.72804(18) 0.0221(5) Uani 1 1 d . . . . .
H31A H 1.017607 0.177885 0.753531 0.026 Uiso 1 1 calc R . . . .
H31B H 0.898807 0.201112 0.688532 0.026 Uiso 1 1 calc R . . . .
C32 C 0.7927(3) 0.2814(3) 0.81001(18) 0.0246(5) Uani 1 1 d . . . . .
H32A H 0.802285 0.352923 0.836925 0.029 Uiso 1 1 calc R . . . .
H32B H 0.802204 0.192178 0.859604 0.029 Uiso 1 1 calc R . . . .
C33 C 0.6326(3) 0.3419(2) 0.77976(18) 0.0226(5) Uani 1 1 d . . . . .
H33A H 0.616345 0.264972 0.762201 0.027 Uiso 1 1 calc R . . . .
H33B H 0.554594 0.370027 0.833435 0.027 Uiso 1 1 calc R . . . .
C41 C 0.3569(3) 0.7535(3) 0.4399(2) 0.0312(6) Uani 1 1 d . . . . .
H41A H 0.270229 0.806828 0.404536 0.037 Uiso 1 1 calc R . . . .
H41B H 0.442182 0.697337 0.399275 0.037 Uiso 1 1 calc R . . . .
C42 C 0.4036(3) 0.8618(2) 0.46527(19) 0.0252(5) Uani 1 1 d . . . . .
H42A H 0.331104 0.898346 0.518641 0.030 Uiso 1 1 calc R . . . .
H42B H 0.398924 0.944975 0.411371 0.030 Uiso 1 1 calc R . . . .
C43 C 0.5657(3) 0.7924(2) 0.49158(19) 0.0248(5) Uani 1 1 d . . . . .
H43A H 0.639083 0.763450 0.436392 0.030 Uiso 1 1 calc R . . . .
H43B H 0.589907 0.864964 0.508847 0.030 Uiso 1 1 calc R . . . .


_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 Cu2 3.0541(4) . ?
Cu1 O1 1.9728(15) . ?
Cu1 O3 1.9344(14) . ?
Cu1 O4 1.9421(15) . ?
Cu1 N1 2.3088(17) . ?
Cu1 N3 1.984(2) . ?
Cu2 O2 1.9695(16) . ?
Cu2 O3 1.9626(15) . ?
Cu2 O4 1.9174(15) . ?
Cu2 N2 2.308(2) . ?
Cu2 N4 2.004(2) . ?
O1 C19 1.280(2) . ?
O2 C29 1.270(3) . ?
O3 C33 1.402(3) . ?
O4 C43 1.407(3) . ?
O11 C19 1.228(3) . ?
O22 C29 1.235(3) . ?
N1 C10 1.363(3) . ?
N1 C18 1.323(3) . ?
N2 C20 1.376(3) . ?
N2 C28 1.330(3) . ?
N3 C31 1.481(3) . ?
N4 C41 1.485(4) . ?
C10 C11 1.414(3) . ?
C10 C15 1.430(3) . ?
C11 C12 1.366(3) . ?
C12 C13 1.411(3) . ?
C13 C14 1.364(3) . ?
C14 C15 1.410(3) . ?
C15 C16 1.412(3) . ?
C16 C17 1.357(3) . ?
C17 C18 1.417(3) . ?
C18 C19 1.516(3) . ?
C20 C21 1.416(3) . ?
C20 C25 1.411(3) . ?
C21 C22 1.377(3) . ?
C22 C23 1.398(4) . ?
C23 C24 1.370(4) . ?
C24 C25 1.422(3) . ?
C25 C26 1.416(3) . ?
C26 C27 1.361(3) . ?
C27 C28 1.400(4) . ?
C28 C29 1.531(3) . ?
C31 C32 1.522(3) . ?
C32 C33 1.529(3) . ?
C41 C42 1.508(3) . ?
C42 C43 1.519(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 Cu2 129.40(5) . . ?
O1 Cu1 N1 77.69(6) . . ?
O1 Cu1 N3 92.23(8) . . ?
O3 Cu1 Cu2 38.73(4) . . ?
O3 Cu1 O1 167.22(6) . . ?
O3 Cu1 O4 76.06(6) . . ?
O3 Cu1 N1 110.10(7) . . ?
O3 Cu1 N3 96.55(7) . . ?
O4 Cu1 Cu2 37.41(4) . . ?
O4 Cu1 O1 92.55(6) . . ?
O4 Cu1 N1 102.46(6) . . ?
O4 Cu1 N3 159.56(8) . . ?
N1 Cu1 Cu2 112.61(4) . . ?
N3 Cu1 Cu2 131.58(6) . . ?
N3 Cu1 N1 97.98(8) . . ?
O2 Cu2 Cu1 135.19(5) . . ?
O2 Cu2 N2 77.95(7) . . ?
O2 Cu2 N4 88.23(9) . . ?
O3 Cu2 Cu1 38.07(4) . . ?
O3 Cu2 O2 98.28(7) . . ?
O3 Cu2 N2 95.29(7) . . ?
O3 Cu2 N4 156.95(10) . . ?
O4 Cu2 Cu1 37.97(4) . . ?
O4 Cu2 O2 169.21(7) . . ?
O4 Cu2 O3 75.96(6) . . ?
O4 Cu2 N2 111.38(7) . . ?
O4 Cu2 N4 93.76(9) . . ?
N2 Cu2 Cu1 108.70(4) . . ?
N4 Cu2 Cu1 127.78(8) . . ?
N4 Cu2 N2 107.71(10) . . ?
C19 O1 Cu1 120.54(16) . . ?
C29 O2 Cu2 120.58(14) . . ?
Cu1 O3 Cu2 103.20(7) . . ?
C33 O3 Cu1 129.19(13) . . ?
C33 O3 Cu2 127.39(13) . . ?
Cu2 O4 Cu1 104.62(7) . . ?
C43 O4 Cu1 125.99(13) . . ?
C43 O4 Cu2 129.39(13) . . ?
C10 N1 Cu1 133.03(13) . . ?
C18 N1 Cu1 107.54(15) . . ?
C18 N1 C10 119.19(18) . . ?
C20 N2 Cu2 134.05(15) . . ?
C28 N2 Cu2 106.96(14) . . ?
C28 N2 C20 117.6(2) . . ?
C31 N3 Cu1 116.20(15) . . ?
C41 N4 Cu2 119.12(15) . . ?
N1 C10 C11 119.66(18) . . ?
N1 C10 C15 121.3(2) . . ?
C11 C10 C15 119.0(2) . . ?
C12 C11 C10 120.3(2) . . ?
C11 C12 C13 120.9(2) . . ?
C14 C13 C12 119.9(2) . . ?
C13 C14 C15 121.2(2) . . ?
C14 C15 C10 118.7(2) . . ?
C14 C15 C16 124.1(2) . . ?
C16 C15 C10 117.2(2) . . ?
C17 C16 C15 120.83(19) . . ?
C16 C17 C18 118.3(2) . . ?
N1 C18 C17 123.2(2) . . ?
N1 C18 C19 117.08(18) . . ?
C17 C18 C19 119.75(19) . . ?
O1 C19 C18 116.66(19) . . ?
O11 C19 O1 124.7(2) . . ?
O11 C19 C18 118.58(19) . . ?
N2 C20 C21 118.4(2) . . ?
N2 C20 C25 121.9(2) . . ?
C25 C20 C21 119.7(2) . . ?
C22 C21 C20 119.7(2) . . ?
C21 C22 C23 121.0(2) . . ?
C24 C23 C22 120.2(2) . . ?
C23 C24 C25 120.6(2) . . ?
C20 C25 C24 118.7(2) . . ?
C20 C25 C26 118.2(2) . . ?
C26 C25 C24 123.1(2) . . ?
C27 C26 C25 119.1(2) . . ?
C26 C27 C28 119.4(2) . . ?
N2 C28 C27 123.7(2) . . ?
N2 C28 C29 116.1(2) . . ?
C27 C28 C29 120.1(2) . . ?
O2 C29 C28 116.64(19) . . ?
O22 C29 O2 125.9(2) . . ?
O22 C29 C28 117.5(2) . . ?
N3 C31 C32 110.96(19) . . ?
C31 C32 C33 113.2(2) . . ?
O3 C33 C32 112.10(18) . . ?
N4 C41 C42 111.2(2) . . ?
C41 C42 C43 111.95(19) . . ?
O4 C43 C42 112.24(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
_geom_hbond_publ_flag
N3 H3B O1 0.80(3) 2.25(3) 3.025(3) 164(3) 2_766 yes
N4 H4A O11 0.74(3) 2.47(3) 3.002(3) 131(3) 1_455 yes

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.773
_oxdiff_exptl_absorpt_empirical_full_min 0.748
####################################################################### 
# 
# 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_g
_database_code_depnum_ccdc_archive 'CCDC 2076995'
loop_
_audit_author_name
_audit_author_address
'Barbara Modec'
;University of Ljubljana
Slovenia
;
_audit_update_record             
;
2021-04-12 deposited with the CCDC.	2022-03-18 downloaded from the CCDC.
;
_audit_creation_date             2021-03-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H12 Cu N2 O4'
_chemical_formula_sum            'C20 H12 Cu N2 O4'
_chemical_formula_weight         407.86
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   4.8617(2)
_cell_length_b                   13.5497(5)
_cell_length_c                   12.2556(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.467(3)
_cell_angle_gamma                90
_cell_volume                     802.20(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    6144
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      30.0940
_cell_measurement_theta_min      3.4040
_shelx_estimated_absorpt_T_max   0.768
_shelx_estimated_absorpt_T_min   0.442
_exptl_absorpt_coefficient_mu    1.393
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64243
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.689
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             414
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0283
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12501
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.256
_diffrn_reflns_theta_min         3.007
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     37.00 103.00   1.00    2.50    --   14.21-178.00 120.00   66
  2  ω    -75.00 104.00   1.00    2.50    --   14.21   0.00 -60.00  179
  3  ω    -75.00 104.00   1.00    2.50    --   14.21   0.00 150.00  179
  4  ω    -48.00  21.00   1.00    2.50    --  -14.52  77.00 150.00   69
  5  ω   -103.00 -74.00   1.00    2.50    --  -14.52 178.00-180.00   29
  6  ω    -42.00  19.00   1.00    2.50    --  -14.52 -77.00 -90.00   61
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1061535000
_diffrn_orient_matrix_UB_12      -0.0340680000
_diffrn_orient_matrix_UB_13      0.0181278000
_diffrn_orient_matrix_UB_21      -0.0336534000
_diffrn_orient_matrix_UB_22      -0.0283534000
_diffrn_orient_matrix_UB_23      -0.0483359000
_diffrn_orient_matrix_UB_31      0.0956991000
_diffrn_orient_matrix_UB_32      0.0278142000
_diffrn_orient_matrix_UB_33      -0.0270255000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1987
_reflns_number_total             2202
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.444
_refine_diff_density_min         -0.427
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     124
_refine_ls_number_reflns         2202
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0301
_refine_ls_R_factor_gt           0.0263
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0326P)²+0.5700P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0685
_refine_ls_wR_factor_ref         0.0711
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.500000 0.500000 0.500000 0.01363(8) Uani 1 2 d S T P . .
O1 O 0.2143(2) 0.44639(8) 0.57707(8) 0.0164(2) Uani 1 1 d . . . . .
O11 O -0.1358(2) 0.49021(8) 0.66955(10) 0.0198(2) Uani 1 1 d . . . . .
N1 N 0.3881(2) 0.63142(9) 0.57276(9) 0.0140(2) Uani 1 1 d . . . . .
C10 C 0.4913(3) 0.72641(10) 0.57359(11) 0.0156(3) Uani 1 1 d . . . . .
C11 C 0.6710(3) 0.75554(11) 0.49640(13) 0.0208(3) Uani 1 1 d . . . . .
H11 H 0.718137 0.711136 0.443694 0.025 Uiso 1 1 calc R . . . .
C12 C 0.7753(4) 0.84949(12) 0.49974(14) 0.0265(3) Uani 1 1 d . . . . .
H12 H 0.894103 0.868040 0.448987 0.032 Uiso 1 1 calc R . . . .
C13 C 0.7071(4) 0.91882(12) 0.57809(14) 0.0261(3) Uani 1 1 d . . . . .
H13 H 0.782956 0.981880 0.579423 0.031 Uiso 1 1 calc R . . . .
C14 C 0.5297(3) 0.89318(11) 0.65198(13) 0.0222(3) Uani 1 1 d . . . . .
H14 H 0.482515 0.939250 0.702952 0.027 Uiso 1 1 calc R . . . .
C15 C 0.4169(3) 0.79670(11) 0.65147(12) 0.0178(3) Uani 1 1 d . . . . .
C16 C 0.2269(3) 0.76933(12) 0.72500(12) 0.0215(3) Uani 1 1 d . . . . .
H16 H 0.179309 0.813546 0.777795 0.026 Uiso 1 1 calc R . . . .
C17 C 0.1139(3) 0.67702(11) 0.71755(12) 0.0200(3) Uani 1 1 d . . . . .
H17 H -0.019203 0.658528 0.762460 0.024 Uiso 1 1 calc R . . . .
C18 C 0.2024(3) 0.61042(10) 0.64079(11) 0.0148(3) Uani 1 1 d . . . . .
C19 C 0.0812(3) 0.50810(10) 0.63029(12) 0.0148(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.9089(10) . ?
Cu1 O1 1.9089(10) 3_666 ?
Cu1 N1 2.0907(12) . ?
Cu1 N1 2.0908(12) 3_666 ?
O1 C19 1.2801(17) . ?
O11 C19 1.2318(19) . ?
N1 C10 1.3811(18) . ?
N1 C18 1.3269(18) . ?
C10 C11 1.414(2) . ?
C10 C15 1.4236(19) . ?
C11 C12 1.369(2) . ?
C12 C13 1.409(2) . ?
C13 C14 1.364(2) . ?
C14 C15 1.417(2) . ?
C15 C16 1.411(2) . ?
C16 C17 1.365(2) . ?
C17 C18 1.4056(19) . ?
C18 C19 1.5063(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 180.0 . 3_666 ?
O1 Cu1 N1 97.22(4) . 3_666 ?
O1 Cu1 N1 82.78(4) 3_666 3_666 ?
O1 Cu1 N1 82.78(4) . . ?
O1 Cu1 N1 97.22(4) 3_666 . ?
N1 Cu1 N1 180.00(3) . 3_666 ?
C19 O1 Cu1 116.20(9) . . ?
C10 N1 Cu1 133.25(9) . . ?
C18 N1 Cu1 108.27(9) . . ?
C18 N1 C10 117.87(12) . . ?
N1 C10 C11 120.42(12) . . ?
N1 C10 C15 120.60(13) . . ?
C11 C10 C15 118.98(13) . . ?
C12 C11 C10 119.60(14) . . ?
C11 C12 C13 121.71(15) . . ?
C14 C13 C12 119.82(15) . . ?
C13 C14 C15 120.35(14) . . ?
C14 C15 C10 119.51(13) . . ?
C16 C15 C10 119.11(13) . . ?
C16 C15 C14 121.37(13) . . ?
C17 C16 C15 119.06(13) . . ?
C16 C17 C18 118.81(14) . . ?
N1 C18 C17 124.34(13) . . ?
N1 C18 C19 115.54(12) . . ?
C17 C18 C19 120.12(13) . . ?
O1 C19 C18 115.42(12) . . ?
O11 C19 O1 125.10(13) . . ?
O11 C19 C18 119.46(13) . . ?

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.405
_oxdiff_exptl_absorpt_empirical_full_min 0.563
####################################################################### 
# 
# 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_9f
_database_code_depnum_ccdc_archive 'CCDC 2077005'
loop_
_audit_author_name
_audit_author_address
'Barbara Modec'
;University of Ljubljana
Slovenia
;
_audit_update_record             
;
2021-04-12 deposited with the CCDC.	2022-03-18 downloaded from the CCDC.
;
_audit_creation_date             2021-03-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'C8 H20 Cu N2 O2, 2(C10 H6 N O2), 2(C4 H12 N O)'
_chemical_formula_sum            'C36 H56 Cu N6 O8'
_chemical_formula_weight         764.40
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1133(4)
_cell_length_b                   10.3368(5)
_cell_length_c                   12.0359(5)
_cell_angle_alpha                81.030(4)
_cell_angle_beta                 83.371(4)
_cell_angle_gamma                72.014(4)
_cell_volume                     945.89(8)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    7170
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      30.1880
_cell_measurement_theta_min      3.2250
_shelx_estimated_absorpt_T_max   0.981
_shelx_estimated_absorpt_T_min   0.832
_exptl_absorpt_coefficient_mu    0.635
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94048
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             407
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0318
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.891
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16937
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.891
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.332
_diffrn_reflns_theta_min         2.530
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.891
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -12.00  90.00   1.00   30.00    --   14.05  37.00  90.00  102
  2  ω    -11.00  88.00   1.00   30.00    --   14.05  57.00-180.00   99
  3  ω    -21.00  44.00   1.00   30.00    --   14.05 -57.00-180.00   65
  4  ω    -10.00  88.00   1.00   30.00    --   14.05  57.00 -60.00   98
  5  ω    -40.00   7.00   1.00   30.00    --   14.05 -77.00 150.00   47
  6  ω    -42.00  48.00   1.00   30.00    --   14.05 -77.00  30.00   90
  7  ω    -48.00  21.00   1.00   30.00    --  -14.36  77.00 -60.00   69
  8  ω    -13.00  19.00   1.00   30.00    --  -14.36 -77.00 -90.00   32
  9  ω    -93.00 -45.00   1.00   30.00    --  -14.36 156.00  23.51   48
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0494504000
_diffrn_orient_matrix_UB_12      -0.0273795000
_diffrn_orient_matrix_UB_13      -0.0296516000
_diffrn_orient_matrix_UB_21      0.0044627000
_diffrn_orient_matrix_UB_22      0.0493680000
_diffrn_orient_matrix_UB_23      -0.0474044000
_diffrn_orient_matrix_UB_31      0.0776336000
_diffrn_orient_matrix_UB_32      -0.0458668000
_diffrn_orient_matrix_UB_33      -0.0212481000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4523
_reflns_number_total             5069
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.423
_refine_diff_density_min         -0.559
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         5069
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0402
_refine_ls_R_factor_gt           0.0336
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0348P)²+0.5783P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0877
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C32(H32A,H32B)
2.b Aromatic/amide H refined with riding coordinates:
 C21(H21), C22(H22), C23(H23), C24(H24), C26(H26), C27(H27)
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C33(H33A,H33B,H33C), C34(H34A,H34B,
 H34C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 -0.500000 1.000000 1.000000 0.01410(8) Uani 1 2 d S T P . .
O1 O -0.30125(13) 1.05731(10) 0.93895(8) 0.0156(2) Uani 1 1 d . . . . .
O2 O 0.61117(16) 0.57989(12) 0.88758(10) 0.0269(3) Uani 1 1 d . . . . .
O3 O -0.05783(14) 0.86590(11) 1.05344(9) 0.0177(2) Uani 1 1 d . . . . .
H3 H -0.113(3) 0.923(2) 1.0156(19) 0.035(6) Uiso 1 1 d . . . . .
O22 O 0.5954(2) 0.76783(13) 0.76491(12) 0.0431(4) Uani 1 1 d . . . . .
N1 N -0.56527(18) 1.02948(14) 0.84130(11) 0.0157(2) Uani 1 1 d . . . . .
H1A H -0.534(3) 0.955(2) 0.8197(19) 0.034(6) Uiso 1 1 d . . . . .
H1B H -0.671(3) 1.061(2) 0.8380(17) 0.025(5) Uiso 1 1 d . . . . .
N2 N 0.82438(17) 0.43155(13) 0.72345(11) 0.0179(3) Uani 1 1 d . . . . .
N3 N 0.28870(17) 0.69541(14) 1.00216(11) 0.0160(2) Uani 1 1 d . . . . .
H3A H 0.277(3) 0.774(2) 1.0266(16) 0.023(5) Uiso 1 1 d . . . . .
H3B H 0.291(3) 0.636(2) 1.0573(18) 0.023(5) Uiso 1 1 d . . . . .
H3C H 0.385(3) 0.669(2) 0.9658(17) 0.027(5) Uiso 1 1 d . . . . .
C11 C -0.46940(19) 1.12032(15) 0.77400(12) 0.0161(3) Uani 1 1 d . . . . .
C12 C -0.28922(19) 1.06960(17) 0.81968(12) 0.0191(3) Uani 1 1 d . . . . .
H12A H -0.226790 0.981151 0.795408 0.023 Uiso 1 1 calc R . . . .
H12B H -0.224292 1.133359 0.789172 0.023 Uiso 1 1 calc R . . . .
C13 C -0.5626(2) 1.26678(16) 0.79725(14) 0.0230(3) Uani 1 1 d . . . . .
H13A H -0.676799 1.295185 0.770303 0.035 Uiso 1 1 calc GR . . . .
H13B H -0.498070 1.326538 0.759185 0.035 Uiso 1 1 calc GR . . . .
H13C H -0.571684 1.270969 0.876929 0.035 Uiso 1 1 calc GR . . . .
C14 C -0.4548(2) 1.10834(18) 0.64819(13) 0.0250(3) Uani 1 1 d . . . . .
H14A H -0.407503 1.013656 0.636804 0.037 Uiso 1 1 calc GR . . . .
H14B H -0.379774 1.159107 0.609062 0.037 Uiso 1 1 calc GR . . . .
H14C H -0.567898 1.144709 0.619580 0.037 Uiso 1 1 calc GR . . . .
C20 C 0.8943(2) 0.35328(16) 0.63785(13) 0.0191(3) Uani 1 1 d . . . . .
C21 C 1.0149(2) 0.22269(16) 0.66342(14) 0.0211(3) Uani 1 1 d . . . . .
H21 H 1.048582 0.193107 0.736654 0.025 Uiso 1 1 calc R . . . .
C22 C 1.0825(2) 0.13954(18) 0.58090(15) 0.0276(4) Uani 1 1 d . . . . .
H22 H 1.161445 0.053705 0.598723 0.033 Uiso 1 1 calc R . . . .
C23 C 1.0340(3) 0.1824(2) 0.46964(16) 0.0379(5) Uani 1 1 d . . . . .
H23 H 1.080019 0.124593 0.414515 0.045 Uiso 1 1 calc R . . . .
C24 C 0.9196(3) 0.3084(2) 0.44232(16) 0.0421(5) Uani 1 1 d . . . . .
H24 H 0.888962 0.336317 0.368336 0.050 Uiso 1 1 calc R . . . .
C25 C 0.8468(3) 0.39742(18) 0.52535(14) 0.0293(4) Uani 1 1 d . . . . .
C26 C 0.7289(3) 0.5294(2) 0.50219(16) 0.0413(5) Uani 1 1 d . . . . .
H26 H 0.694229 0.562110 0.429499 0.050 Uiso 1 1 calc R . . . .
C27 C 0.6666(3) 0.60833(19) 0.58664(15) 0.0344(4) Uani 1 1 d . . . . .
H27 H 0.592535 0.696872 0.571884 0.041 Uiso 1 1 calc R . . . .
C28 C 0.7156(2) 0.55449(16) 0.69727(13) 0.0206(3) Uani 1 1 d . . . . .
C29 C 0.6355(2) 0.64196(16) 0.79200(14) 0.0226(3) Uani 1 1 d . . . . .
C31 C 0.14218(19) 0.70858(14) 0.93119(12) 0.0155(3) Uani 1 1 d . . . . .
C32 C -0.02603(19) 0.74190(15) 1.00704(13) 0.0179(3) Uani 1 1 d . . . . .
H32A H -0.122543 0.748698 0.963573 0.021 Uiso 1 1 calc R . . . .
H32B H -0.019807 0.667400 1.067904 0.021 Uiso 1 1 calc R . . . .
C33 C 0.1720(2) 0.57095(16) 0.88895(14) 0.0236(3) Uani 1 1 d . . . . .
H33A H 0.275181 0.552009 0.838892 0.035 Uiso 1 1 calc GR . . . .
H33B H 0.074196 0.574282 0.849450 0.035 Uiso 1 1 calc GR . . . .
H33C H 0.185291 0.499918 0.951923 0.035 Uiso 1 1 calc GR . . . .
C34 C 0.1423(2) 0.82165(15) 0.83342(13) 0.0197(3) Uani 1 1 d . . . . .
H34A H 0.116014 0.907933 0.862094 0.029 Uiso 1 1 calc GR . . . .
H34B H 0.056257 0.826156 0.783323 0.029 Uiso 1 1 calc GR . . . .
H34C H 0.254759 0.802075 0.793257 0.029 Uiso 1 1 calc GR . . . .


_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 O1 1.9162(10) . ?
Cu1 O1 1.9162(10) 2_477 ?
Cu1 N1 1.9935(13) . ?
Cu1 N1 1.9935(13) 2_477 ?
O1 C12 1.4159(17) . ?
O2 C29 1.253(2) . ?
O3 C32 1.4167(18) . ?
O22 C29 1.239(2) . ?
N1 C11 1.4871(19) . ?
N2 C20 1.3709(19) . ?
N2 C28 1.319(2) . ?
N3 C31 1.5032(19) . ?
C11 C12 1.529(2) . ?
C11 C13 1.523(2) . ?
C11 C14 1.527(2) . ?
C20 C21 1.414(2) . ?
C20 C25 1.417(2) . ?
C21 C22 1.369(2) . ?
C22 C23 1.405(3) . ?
C23 C24 1.362(3) . ?
C24 C25 1.418(2) . ?
C25 C26 1.411(3) . ?
C26 C27 1.356(3) . ?
C27 C28 1.412(2) . ?
C28 C29 1.526(2) . ?
C31 C32 1.528(2) . ?
C31 C33 1.525(2) . ?
C31 C34 1.524(2) . ?

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 Cu1 O1 180.00(6) . 2_477 ?
O1 Cu1 N1 86.05(5) 2_477 2_477 ?
O1 Cu1 N1 86.05(5) . . ?
O1 Cu1 N1 93.95(5) . 2_477 ?
O1 Cu1 N1 93.95(5) 2_477 . ?
N1 Cu1 N1 180.0 2_477 . ?
C12 O1 Cu1 110.41(9) . . ?
C11 N1 Cu1 107.69(9) . . ?
C28 N2 C20 117.72(13) . . ?
N1 C11 C12 104.18(11) . . ?
N1 C11 C13 107.92(12) . . ?
N1 C11 C14 112.10(13) . . ?
C13 C11 C12 110.98(13) . . ?
C13 C11 C14 111.28(13) . . ?
C14 C11 C12 110.16(12) . . ?
O1 C12 C11 111.11(12) . . ?
N2 C20 C21 118.71(14) . . ?
N2 C20 C25 122.29(14) . . ?
C21 C20 C25 118.98(14) . . ?
C22 C21 C20 120.34(15) . . ?
C21 C22 C23 120.78(16) . . ?
C24 C23 C22 120.13(17) . . ?
C23 C24 C25 120.78(18) . . ?
C24 C25 C20 118.98(16) . . ?
C26 C25 C20 117.56(15) . . ?
C26 C25 C24 123.46(17) . . ?
C27 C26 C25 119.55(16) . . ?
C26 C27 C28 119.24(16) . . ?
N2 C28 C27 123.52(15) . . ?
N2 C28 C29 118.19(14) . . ?
C27 C28 C29 118.27(14) . . ?
O2 C29 C28 117.05(14) . . ?
O22 C29 O2 126.82(16) . . ?
O22 C29 C28 116.07(15) . . ?
N3 C31 C32 107.44(12) . . ?
N3 C31 C33 108.05(12) . . ?
N3 C31 C34 108.18(12) . . ?
C33 C31 C32 109.63(13) . . ?
C34 C31 C32 112.13(12) . . ?
C34 C31 C33 111.24(12) . . ?
O3 C32 C31 112.63(12) . . ?

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
_geom_hbond_publ_flag
O3 H3 O1 0.75(2) 1.93(2) 2.6606(16) 166(2) . yes
N1 H1A O22 0.81(2) 2.06(2) 2.8603(18) 169(2) 1_455 yes
N3 H3A O1 0.88(2) 1.93(2) 2.7909(17) 167.0(18) 2_577 yes
N3 H3B O2 0.83(2) 2.15(2) 2.8570(18) 143.2(18) 2_667 yes
N3 H3C O2 0.84(2) 1.98(2) 2.8149(18) 172(2) . yes

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.412
_oxdiff_exptl_absorpt_empirical_full_min 0.786
####################################################################### 
# 
# 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_8b
_database_code_depnum_ccdc_archive 'CCDC 2077001'
loop_
_audit_author_name
_audit_author_address
'Barbara Modec'
;University of Ljubljana
Slovenia
;
_audit_update_record             
;
2021-04-12 deposited with the CCDC.	2022-03-18 downloaded from the CCDC.
;
_audit_creation_date             2021-03-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H21 Cu N3 O5'
_chemical_formula_sum            'C23 H21 Cu N3 O5'
_chemical_formula_weight         482.97
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8642(6)
_cell_length_b                   10.1622(6)
_cell_length_c                   13.7176(8)
_cell_angle_alpha                106.140(5)
_cell_angle_beta                 93.452(5)
_cell_angle_gamma                115.573(6)
_cell_volume                     1047.28(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4467
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      29.8020
_cell_measurement_theta_min      3.1480
_shelx_estimated_absorpt_T_max   0.899
_shelx_estimated_absorpt_T_min   0.737
_exptl_absorpt_coefficient_mu    1.085
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70969
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             498
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_unetI/netI     0.0442
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.875
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            10446
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.875
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.168
_diffrn_reflns_theta_min         2.356
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.875
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     26.00  56.00   1.00   10.00    --   14.05 -99.00 120.00   30
  2  ω    -44.00  39.00   1.00   10.00    --   14.05 -37.00  60.00   83
  3  ω    -40.00  43.00   1.00   10.00    --   14.05 -77.00-150.00   83
  4  ω    -16.00  88.00   1.00   10.00    --   14.05  57.00   0.00  104
  5  ω    -42.00  -7.00   1.00   10.00    --  -14.36 -77.00   0.00   35
  6  ω    -18.00  10.00   1.00   10.00    --  -14.36 -77.00 120.00   28
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0575260000
_diffrn_orient_matrix_UB_12      -0.0506601000
_diffrn_orient_matrix_UB_13      0.0226608000
_diffrn_orient_matrix_UB_21      0.0672712000
_diffrn_orient_matrix_UB_22      -0.0102694000
_diffrn_orient_matrix_UB_23      0.0214992000
_diffrn_orient_matrix_UB_31      0.0197601000
_diffrn_orient_matrix_UB_32      0.0639190000
_diffrn_orient_matrix_UB_33      0.0453079000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4708
_reflns_number_total             5431
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.417
_refine_diff_density_min         -0.582
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         5431
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0367
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0247P)²+0.5673P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0795
_refine_ls_wR_factor_ref         0.0840
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C31(H31)
2.b Secondary CH2 refined with riding coordinates:
 C32(H32A,H32B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17), C21(H21),
 C22(H22), C23(H23), C24(H24), C26(H26), C27(H27)
2.d Idealised Me refined as rotating group:
 C33(H33A,H33B,H33C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.57912(3) 0.48585(3) 0.24168(2) 0.01719(7) Uani 1 1 d . . . . .
O1 O 0.55009(17) 0.39871(15) 0.35243(10) 0.0186(3) Uani 1 1 d . . . . .
O2 O 0.62615(18) 0.58931(16) 0.13831(10) 0.0206(3) Uani 1 1 d . . . . .
O3 O 0.2764(2) 0.29532(18) 0.15030(12) 0.0254(3) Uani 1 1 d . . . . .
H3 H 0.273(4) 0.309(3) 0.098(2) 0.047(9) Uiso 1 1 d . . . . .
O11 O 0.65631(19) 0.40178(18) 0.50430(11) 0.0267(3) Uani 1 1 d . . . . .
O22 O 0.78890(18) 0.62763(17) 0.02051(10) 0.0238(3) Uani 1 1 d . . . . .
N1 N 0.8295(2) 0.66602(18) 0.37151(12) 0.0177(3) Uani 1 1 d . . . . .
N2 N 0.65630(19) 0.34375(18) 0.14128(12) 0.0159(3) Uani 1 1 d . . . . .
N3 N 0.4551(2) 0.6070(2) 0.29952(13) 0.0201(3) Uani 1 1 d . . . . .
H3A H 0.519(3) 0.704(3) 0.3113(19) 0.038(7) Uiso 1 1 d . . . . .
H3B H 0.443(3) 0.613(3) 0.364(2) 0.034(7) Uiso 1 1 d . . . . .
C10 C 0.9698(2) 0.8032(2) 0.38109(16) 0.0215(4) Uani 1 1 d . . . . .
C11 C 0.9729(3) 0.8727(2) 0.30494(17) 0.0279(5) Uani 1 1 d . . . . .
H11 H 0.880205 0.826551 0.249610 0.034 Uiso 1 1 calc R . . . .
C12 C 1.1133(3) 1.0090(3) 0.3127(2) 0.0372(6) Uani 1 1 d . . . . .
H12 H 1.114807 1.054313 0.262179 0.045 Uiso 1 1 calc R . . . .
C13 C 1.2538(3) 1.0804(3) 0.3954(2) 0.0428(7) Uani 1 1 d . . . . .
H13 H 1.347600 1.172652 0.399561 0.051 Uiso 1 1 calc R . . . .
C14 C 1.2536(3) 1.0157(3) 0.46956(19) 0.0378(6) Uani 1 1 d . . . . .
H14 H 1.348007 1.063996 0.523953 0.045 Uiso 1 1 calc R . . . .
C15 C 1.1112(3) 0.8750(2) 0.46559(16) 0.0270(5) Uani 1 1 d . . . . .
C16 C 1.1052(3) 0.8020(3) 0.53900(17) 0.0301(5) Uani 1 1 d . . . . .
H16 H 1.197467 0.845114 0.594142 0.036 Uiso 1 1 calc R . . . .
C17 C 0.9638(3) 0.6675(3) 0.52959(15) 0.0249(4) Uani 1 1 d . . . . .
H17 H 0.957485 0.618778 0.578552 0.030 Uiso 1 1 calc R . . . .
C18 C 0.8276(2) 0.6039(2) 0.44425(14) 0.0178(4) Uani 1 1 d . . . . .
C19 C 0.6658(2) 0.4564(2) 0.43372(14) 0.0174(4) Uani 1 1 d . . . . .
C20 C 0.6510(2) 0.2050(2) 0.13658(14) 0.0185(4) Uani 1 1 d . . . . .
C21 C 0.5661(3) 0.1267(2) 0.20281(16) 0.0251(4) Uani 1 1 d . . . . .
H21 H 0.514804 0.169396 0.250127 0.030 Uiso 1 1 calc R . . . .
C22 C 0.5595(3) -0.0125(3) 0.19700(18) 0.0324(5) Uani 1 1 d . . . . .
H22 H 0.503301 -0.063531 0.240838 0.039 Uiso 1 1 calc R . . . .
C23 C 0.6358(3) -0.0802(3) 0.12627(18) 0.0343(6) Uani 1 1 d . . . . .
H23 H 0.630778 -0.174334 0.124170 0.041 Uiso 1 1 calc R . . . .
C24 C 0.7167(3) -0.0079(3) 0.06127(18) 0.0315(5) Uani 1 1 d . . . . .
H24 H 0.767048 -0.052864 0.014679 0.038 Uiso 1 1 calc R . . . .
C25 C 0.7255(3) 0.1355(2) 0.06338(16) 0.0227(4) Uani 1 1 d . . . . .
C26 C 0.8046(3) 0.2128(2) -0.00461(16) 0.0255(5) Uani 1 1 d . . . . .
H26 H 0.857393 0.171815 -0.051750 0.031 Uiso 1 1 calc R . . . .
C27 C 0.8034(2) 0.3476(2) -0.00093(15) 0.0216(4) Uani 1 1 d . . . . .
H27 H 0.852705 0.398348 -0.046480 0.026 Uiso 1 1 calc R . . . .
C28 C 0.7266(2) 0.4087(2) 0.07282(14) 0.0171(4) Uani 1 1 d . . . . .
C29 C 0.7153(2) 0.5546(2) 0.07639(14) 0.0178(4) Uani 1 1 d . . . . .
C31 C 0.2865(3) 0.5453(2) 0.23231(15) 0.0212(4) Uani 1 1 d . . . . .
H31 H 0.305571 0.563523 0.166564 0.025 Uiso 1 1 calc R . . . .
C32 C 0.1928(3) 0.3717(3) 0.20958(16) 0.0258(5) Uani 1 1 d . . . . .
H32A H 0.185912 0.350956 0.274478 0.031 Uiso 1 1 calc R . . . .
H32B H 0.077124 0.330548 0.171710 0.031 Uiso 1 1 calc R . . . .
C33 C 0.1825(3) 0.6236(3) 0.27895(17) 0.0287(5) Uani 1 1 d . . . . .
H33A H 0.161021 0.606155 0.343174 0.043 Uiso 1 1 calc GR . . . .
H33B H 0.075789 0.581081 0.231558 0.043 Uiso 1 1 calc GR . . . .
H33C H 0.245165 0.732913 0.291576 0.043 Uiso 1 1 calc GR . . . .


_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 O1 1.9381(13) . ?
Cu1 O2 1.9524(14) . ?
Cu1 N1 2.3775(16) . ?
Cu1 N2 2.0762(15) . ?
Cu1 N3 2.0209(18) . ?
O1 C19 1.272(2) . ?
O2 C29 1.274(2) . ?
O3 C32 1.426(2) . ?
O11 C19 1.234(2) . ?
O22 C29 1.234(2) . ?
N1 C10 1.375(2) . ?
N1 C18 1.318(3) . ?
N2 C20 1.373(2) . ?
N2 C28 1.329(2) . ?
N3 C31 1.476(3) . ?
C10 C11 1.410(3) . ?
C10 C15 1.419(3) . ?
C11 C12 1.376(3) . ?
C12 C13 1.399(4) . ?
C13 C14 1.356(4) . ?
C14 C15 1.425(3) . ?
C15 C16 1.398(3) . ?
C16 C17 1.364(3) . ?
C17 C18 1.407(3) . ?
C18 C19 1.524(3) . ?
C20 C21 1.412(3) . ?
C20 C25 1.425(3) . ?
C21 C22 1.370(3) . ?
C22 C23 1.408(3) . ?
C23 C24 1.355(3) . ?
C24 C25 1.417(3) . ?
C25 C26 1.410(3) . ?
C26 C27 1.361(3) . ?
C27 C28 1.404(3) . ?
C28 C29 1.517(3) . ?
C31 C32 1.515(3) . ?
C31 C33 1.521(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O2 175.00(6) . . ?
O1 Cu1 N1 76.77(6) . . ?
O1 Cu1 N2 100.04(6) . . ?
O1 Cu1 N3 91.41(7) . . ?
O2 Cu1 N1 98.25(6) . . ?
O2 Cu1 N2 81.55(6) . . ?
O2 Cu1 N3 88.15(7) . . ?
N2 Cu1 N1 104.18(6) . . ?
N3 Cu1 N1 91.02(6) . . ?
N3 Cu1 N2 162.67(6) . . ?
C19 O1 Cu1 122.31(12) . . ?
C29 O2 Cu1 115.38(13) . . ?
C10 N1 Cu1 135.23(14) . . ?
C18 N1 Cu1 106.22(12) . . ?
C18 N1 C10 118.31(17) . . ?
C20 N2 Cu1 132.13(13) . . ?
C28 N2 Cu1 109.61(13) . . ?
C28 N2 C20 118.23(16) . . ?
C31 N3 Cu1 111.65(12) . . ?
N1 C10 C11 119.12(19) . . ?
N1 C10 C15 121.2(2) . . ?
C11 C10 C15 119.70(19) . . ?
C12 C11 C10 119.8(2) . . ?
C11 C12 C13 121.0(2) . . ?
C14 C13 C12 120.2(2) . . ?
C13 C14 C15 121.2(2) . . ?
C10 C15 C14 118.1(2) . . ?
C16 C15 C10 118.28(19) . . ?
C16 C15 C14 123.6(2) . . ?
C17 C16 C15 119.9(2) . . ?
C16 C17 C18 118.6(2) . . ?
N1 C18 C17 123.67(18) . . ?
N1 C18 C19 116.63(16) . . ?
C17 C18 C19 119.70(18) . . ?
O1 C19 C18 117.37(17) . . ?
O11 C19 O1 124.76(18) . . ?
O11 C19 C18 117.88(17) . . ?
N2 C20 C21 119.88(18) . . ?
N2 C20 C25 121.09(18) . . ?
C21 C20 C25 119.00(19) . . ?
C22 C21 C20 119.6(2) . . ?
C21 C22 C23 121.6(2) . . ?
C24 C23 C22 119.8(2) . . ?
C23 C24 C25 120.8(2) . . ?
C24 C25 C20 119.1(2) . . ?
C26 C25 C20 118.23(19) . . ?
C26 C25 C24 122.7(2) . . ?
C27 C26 C25 119.70(19) . . ?
C26 C27 C28 118.89(19) . . ?
N2 C28 C27 123.76(19) . . ?
N2 C28 C29 115.60(16) . . ?
C27 C28 C29 120.62(18) . . ?
O2 C29 C28 115.00(17) . . ?
O22 C29 O2 125.88(19) . . ?
O22 C29 C28 119.12(17) . . ?
N3 C31 C32 107.98(17) . . ?
N3 C31 C33 112.92(16) . . ?
C32 C31 C33 111.81(17) . . ?
O3 C32 C31 111.76(17) . . ?

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
_geom_hbond_publ_flag
O3 H3 O22 0.77(3) 2.04(3) 2.773(2) 160(3) 2_665 yes
N3 H3B O11 0.89(3) 2.07(3) 2.933(2) 164(2) 2_666 yes

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.931
_oxdiff_exptl_absorpt_empirical_full_min 0.613
####################################################################### 
# 
# 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_6a
_database_code_depnum_ccdc_archive 'CCDC 2076998'
loop_
_audit_author_name
_audit_author_address
'Barbara Modec'
;University of Ljubljana
Slovenia
;
_audit_update_record             
;
2021-04-12 deposited with the CCDC.	2022-03-18 downloaded from the CCDC.
;
_audit_creation_date             2021-03-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H34 Cu N4 O6'
_chemical_formula_sum            'C28 H34 Cu N4 O6'
_chemical_formula_weight         586.13
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.0630(3)
_cell_length_b                   10.1393(4)
_cell_length_c                   10.9316(4)
_cell_angle_alpha                87.176(3)
_cell_angle_beta                 84.072(3)
_cell_angle_gamma                88.091(3)
_cell_volume                     667.34(5)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    5363
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      75.1580
_cell_measurement_theta_min      4.0160
_shelx_estimated_absorpt_T_max   0.954
_shelx_estimated_absorpt_T_min   0.405
_exptl_absorpt_coefficient_mu    1.577
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.13345
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             307
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0526
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11908
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.145
_diffrn_reflns_theta_min         4.070
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -45.00 -14.00   1.00    1.50    --  -41.57 -57.00  90.00   31
  2  ω    -74.00  34.00   1.00    1.50    --  -41.57  77.00 120.00  108
  3  ω   -114.00 -57.00   1.00    1.50    --  -41.57 -57.00  90.00   57
  4  ω    -81.00 -55.00   1.00    1.50    --  -41.57 -57.00 -30.00   26
  5  ω    -65.00  33.00   1.00    1.50    --  -41.57  37.00  60.00   98
  6  ω    -38.00 -13.00   1.00    1.50    --  -41.57 -57.00 -30.00   25
  7  ω     23.00  85.00   1.00    1.50    --   41.57-125.00 -60.00   62
  8  ω     11.00  36.00   1.00    1.50    --   41.57  77.00 120.00   25
  9  ω      7.00  32.00   1.00    1.50    --   42.00  85.00-151.11   25
 10  ω     17.00  45.00   1.00    1.50    --   46.00  82.00-132.92   28
 11  ω     16.00  41.00   1.00    1.50    --   50.00  82.00  10.60   25
 12  ω     18.00  43.00   1.00    1.50    --   50.00  78.00  75.80   25
 13  ω     17.00  43.00   1.00    1.50    --   50.00  81.00 -72.10   26
 14  ω     72.00 100.00   1.00    1.50    --   58.00  74.00-102.16   28
 15  ω     27.00  52.00   1.00    1.50    --   58.00  74.00-102.16   25
 16  ω     30.00  59.00   1.00    1.50    --   62.00  75.00 145.32   29
 17  ω     34.00  66.00   1.00    1.50    --   66.00  77.00 -26.10   32
 18  ω     68.00 142.00   1.00    1.50    --   66.00  77.00 -26.10   74
 19  ω     34.00  68.00   1.00    1.50    --   66.00  76.00   3.14   34
 20  ω     36.00  62.00   1.00    1.50    --   66.00  76.00 -99.05   26
 21  ω    108.00 134.00   1.00    1.50    --   70.00  76.00  84.23   26
 22  ω    102.00 133.00   1.00    1.50    --   70.00  69.00  32.64   31
 23  ω     38.00  74.00   1.00    1.50    --   70.00  76.00  84.23   36
 24  ω     42.00  74.00   1.00    1.50    --   70.00  69.00  32.64   32
 25  ω     41.00  69.00   1.00    1.50    --   70.00  63.00 -64.80   28
 26  ω     39.00  65.00   1.00    1.50    --   70.00  74.00 172.20   26
 27  ω     41.00  73.00   1.00    1.50    --   74.00  77.00-163.85   32
 28  ω     53.00  91.00   1.00    6.00    --   78.00  47.00 158.24   38
 29  ω     58.00  86.00   1.00    6.00    --   82.00  57.00-110.09   28
 30  ω     57.00  97.00   1.00    6.00    --   86.00  63.00  90.88   40
 31  ω     61.00  99.00   1.00    6.00    --   90.00  67.00  19.31   38
 32  ω     65.00  99.00   1.00    6.00    --   98.00  77.00-104.21   34
 33  ω     78.00 175.00   1.00    6.00    --  109.50  77.00   0.00   97
 34  ω     81.00 126.00   1.00    6.00    --  109.50  61.00 -60.00   45
 35  ω     83.00 174.00   1.00    6.00    --  109.50  77.00-120.00   91
 36  ω     81.00 106.00   1.00    6.00    --  109.50  61.00  30.00   25
 37  ω     75.00 118.00   1.00    6.00    --  109.50-125.00-150.00   43
 38  ω     77.00 144.00   1.00    6.00    --  109.50  77.00 -30.00   67
 39  ω    111.00 177.00   1.00    6.00    --  109.50  77.00 120.00   66
 40  ω     77.00 105.00   1.00    6.00    --  109.50  77.00 120.00   28
 41  ω     79.00 177.00   1.00    6.00    --  109.50  77.00  30.00   98
 42  ω     80.00 176.00   1.00    6.00    --  109.50  77.00  60.00   96
 43  ω     74.00 100.00   1.00    6.00    --  109.50 -94.00  90.00   26
 44  ω     81.00 168.00   1.00    6.00    --  109.50  77.00 -60.00   87
 45  ω     77.00 178.00   1.00    6.00    --  109.50  77.00-150.00  101
 46  ω     49.00 108.00   1.00    6.00    --  109.50 -94.00 -60.00   59
 47  ω     74.00 109.00   1.00    6.00    --  109.50 -94.00  30.00   35
 48  ω     32.00  58.00   1.00    6.00    --  109.50 -94.00  30.00   26
 49  ω     86.00 111.00   1.00    6.00    --  109.50  61.00 -30.00   25
 50  ω     85.00 150.00   1.00    6.00    --  109.50  61.00-180.00   65
 51  ω     27.00 104.00   1.00    6.00    --  109.50 -94.00-150.00   77
 52  ω     54.00 132.00   1.00    6.00    --  109.50 -61.00 -60.00   78
 53  ω     81.00 143.00   1.00    6.00    --  109.50  77.00 150.00   62
 54  ω     80.00 107.00   1.00    6.00    --  109.50  61.00 150.00   27
 55  ω     79.00 172.00   1.00    6.00    --  109.50  77.00  90.00   93
 56  ω     57.00  83.00   1.00    6.00    --  109.50 -61.00-150.00   26
 57  ω    112.00 146.00   1.00    6.00    --  109.50  77.00 -90.00   34
 58  ω     28.00  74.00   1.00    6.00    --  109.50 -94.00 150.00   46
 59  ω     77.00 104.00   1.00    6.00    --  109.50  77.00 -90.00   27
 60  ω     79.00 161.00   1.00    6.00    --  109.50  77.00-180.00   82
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0063400000
_diffrn_orient_matrix_UB_12      -0.0185901000
_diffrn_orient_matrix_UB_13      0.1403264000
_diffrn_orient_matrix_UB_21      -0.0935604000
_diffrn_orient_matrix_UB_22      0.1419224000
_diffrn_orient_matrix_UB_23      0.0160818000
_diffrn_orient_matrix_UB_31      -0.2377346000
_diffrn_orient_matrix_UB_32      -0.0517019000
_diffrn_orient_matrix_UB_33      0.0129383000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2520
_reflns_number_total             2730
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     71.98
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.344
_refine_diff_density_min         -0.499
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     192
_refine_ls_number_reflns         2730
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0388
_refine_ls_R_factor_gt           0.0358
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²+0.3316P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0908
_refine_ls_wR_factor_ref         0.0934
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17)
2.c Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C), C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.500000 0.500000 0.500000 0.01704(12) Uani 1 2 d S T P . .
O1 O 0.7806(2) 0.59631(12) 0.43190(11) 0.0196(3) Uani 1 1 d . . . . .
O2 O 0.2519(3) 0.80653(12) 0.19580(13) 0.0270(3) Uani 1 1 d . . . . .
H2 H 0.160(4) 0.797(2) 0.247(3) 0.031(7) Uiso 1 1 d . . . . .
O11 O 0.9676(2) 0.78332(13) 0.41077(13) 0.0294(3) Uani 1 1 d . . . . .
N1 N 0.4691(2) 0.71006(14) 0.59163(13) 0.0184(3) Uani 1 1 d . . . . .
N2 N 0.3294(2) 0.57642(16) 0.36264(13) 0.0190(3) Uani 1 1 d . . . . .
H2A H 0.278(4) 0.649(3) 0.386(2) 0.032(6) Uiso 1 1 d . . . . .
H2B H 0.223(5) 0.531(3) 0.362(3) 0.040(7) Uiso 1 1 d . . . . .
C10 C 0.3115(3) 0.76686(17) 0.67358(15) 0.0191(3) Uani 1 1 d . . . . .
C11 C 0.1226(3) 0.69430(18) 0.71746(17) 0.0244(4) Uani 1 1 d . . . . .
H11 H 0.107955 0.609032 0.692271 0.029 Uiso 1 1 calc R . . . .
C12 C -0.0398(3) 0.7502(2) 0.79768(17) 0.0275(4) Uani 1 1 d . . . . .
H12 H -0.164715 0.702473 0.826050 0.033 Uiso 1 1 calc R . . . .
C13 C -0.0193(3) 0.8789(2) 0.83733(17) 0.0292(4) Uani 1 1 d . . . . .
H13 H -0.130856 0.915549 0.891189 0.035 Uiso 1 1 calc R . . . .
C14 C 0.1628(3) 0.95001(18) 0.79732(17) 0.0270(4) Uani 1 1 d . . . . .
H14 H 0.175097 1.034639 0.824620 0.032 Uiso 1 1 calc R . . . .
C15 C 0.3345(3) 0.89629(17) 0.71427(16) 0.0219(4) Uani 1 1 d . . . . .
C16 C 0.5258(3) 0.96519(17) 0.66937(18) 0.0256(4) Uani 1 1 d . . . . .
H16 H 0.547182 1.049266 0.695627 0.031 Uiso 1 1 calc R . . . .
C17 C 0.6797(3) 0.90804(17) 0.58719(17) 0.0238(4) Uani 1 1 d . . . . .
H17 H 0.806542 0.952632 0.556122 0.029 Uiso 1 1 calc R . . . .
C18 C 0.6432(3) 0.78013(16) 0.55014(15) 0.0190(3) Uani 1 1 d . . . . .
C19 C 0.8114(3) 0.71513(17) 0.45636(15) 0.0196(3) Uani 1 1 d . . . . .
C21 C 0.4436(3) 0.59955(19) 0.23822(15) 0.0241(4) Uani 1 1 d . . . . .
H21A H 0.483760 0.514612 0.203868 0.029 Uiso 1 1 calc R . . . .
H21B H 0.580118 0.644557 0.245276 0.029 Uiso 1 1 calc R . . . .
C22 C 0.3099(3) 0.68082(16) 0.14749(15) 0.0196(3) Uani 1 1 d . . . . .
C23 C 0.4600(3) 0.7087(2) 0.02954(17) 0.0296(4) Uani 1 1 d . . . . .
H23A H 0.379715 0.761338 -0.027402 0.044 Uiso 1 1 calc GR . . . .
H23B H 0.508239 0.626756 -0.006327 0.044 Uiso 1 1 calc GR . . . .
H23C H 0.586688 0.755555 0.047809 0.044 Uiso 1 1 calc GR . . . .
C24 C 0.1022(3) 0.61238(19) 0.12110(17) 0.0276(4) Uani 1 1 d . . . . .
H24A H 0.007966 0.598061 0.196411 0.041 Uiso 1 1 calc GR . . . .
H24B H 0.142672 0.528998 0.085926 0.041 Uiso 1 1 calc GR . . . .
H24C H 0.024442 0.666794 0.064280 0.041 Uiso 1 1 calc GR . . . .


_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 O1 2.0445(12) . ?
Cu1 O1 2.0445(12) 2_666 ?
Cu1 N1 2.3916(14) 2_666 ?
Cu1 N1 2.3916(14) . ?
Cu1 N2 2.0192(14) 2_666 ?
Cu1 N2 2.0193(14) . ?
O1 C19 1.271(2) . ?
O2 C22 1.423(2) . ?
O11 C19 1.239(2) . ?
N1 C10 1.373(2) . ?
N1 C18 1.321(2) . ?
N2 C21 1.473(2) . ?
C10 C11 1.411(3) . ?
C10 C15 1.422(2) . ?
C11 C12 1.376(3) . ?
C12 C13 1.408(3) . ?
C13 C14 1.361(3) . ?
C14 C15 1.421(3) . ?
C15 C16 1.406(3) . ?
C16 C17 1.362(3) . ?
C17 C18 1.409(2) . ?
C18 C19 1.527(2) . ?
C21 C22 1.537(2) . ?
C22 C23 1.519(2) . ?
C22 C24 1.518(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 180.00(6) . 2_666 ?
O1 Cu1 N1 74.69(5) 2_666 2_666 ?
O1 Cu1 N1 74.69(5) . . ?
O1 Cu1 N1 105.31(5) 2_666 . ?
O1 Cu1 N1 105.31(5) . 2_666 ?
N1 Cu1 N1 180.0 2_666 . ?
N2 Cu1 O1 87.78(6) 2_666 . ?
N2 Cu1 O1 87.78(6) . 2_666 ?
N2 Cu1 O1 92.22(6) . . ?
N2 Cu1 O1 92.22(6) 2_666 2_666 ?
N2 Cu1 N1 89.23(5) 2_666 2_666 ?
N2 Cu1 N1 89.23(5) . . ?
N2 Cu1 N1 90.77(5) . 2_666 ?
N2 Cu1 N1 90.77(5) 2_666 . ?
N2 Cu1 N2 180.0 2_666 . ?
C19 O1 Cu1 121.83(11) . . ?
C10 N1 Cu1 132.97(12) . . ?
C18 N1 Cu1 109.17(10) . . ?
C18 N1 C10 117.86(15) . . ?
C21 N2 Cu1 119.99(11) . . ?
N1 C10 C11 118.68(16) . . ?
N1 C10 C15 121.57(17) . . ?
C11 C10 C15 119.76(16) . . ?
C12 C11 C10 119.74(17) . . ?
C11 C12 C13 120.79(19) . . ?
C14 C13 C12 120.43(17) . . ?
C13 C14 C15 120.70(17) . . ?
C14 C15 C10 118.58(18) . . ?
C16 C15 C10 118.16(16) . . ?
C16 C15 C14 123.26(17) . . ?
C17 C16 C15 119.60(16) . . ?
C16 C17 C18 118.76(18) . . ?
N1 C18 C17 124.04(16) . . ?
N1 C18 C19 116.29(15) . . ?
C17 C18 C19 119.67(16) . . ?
O1 C19 C18 117.72(15) . . ?
O11 C19 O1 125.51(16) . . ?
O11 C19 C18 116.77(15) . . ?
N2 C21 C22 115.38(14) . . ?
O2 C22 C21 109.19(14) . . ?
O2 C22 C23 105.64(15) . . ?
O2 C22 C24 109.84(15) . . ?
C23 C22 C21 108.49(14) . . ?
C24 C22 C21 112.56(15) . . ?
C24 C22 C23 110.88(15) . . ?

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
_geom_hbond_publ_flag
O2 H2 O11 0.75(3) 2.04(3) 2.772(2) 166(3) 1_455 yes
N2 H2A O11 0.83(3) 2.29(3) 3.009(2) 145(2) 1_455 yes

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.493
_oxdiff_exptl_absorpt_empirical_full_min 0.335
####################################################################### 
# 
# 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_anti-4d
_database_code_depnum_ccdc_archive 'CCDC 2076996'
loop_
_audit_author_name
_audit_author_address
'Barbara Modec'
;University of Ljubljana
Slovenia
;
_audit_update_record             
;
2021-04-12 deposited with the CCDC.	2022-03-18 downloaded from the CCDC.
;
_audit_creation_date             2021-03-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H32 Cu2 N4 O6'
_chemical_formula_sum            'C28 H32 Cu2 N4 O6'
_chemical_formula_weight         647.65
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   7.3120(4)
_cell_length_b                   20.7381(11)
_cell_length_c                   8.8408(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.162(5)
_cell_angle_gamma                90
_cell_volume                     1327.01(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2501
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      29.9900
_cell_measurement_theta_min      3.5040
_shelx_estimated_absorpt_T_max   0.952
_shelx_estimated_absorpt_T_min   0.789
_exptl_absorpt_coefficient_mu    1.654
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81459
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.621
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             668
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0596
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.874
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            6747
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.218
_diffrn_reflns_theta_min         2.526
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.874
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -31.00  60.00   1.00   65.00    --   14.05 -19.00  90.00   91
  2  ω    -37.00  37.00   1.00   65.00    --   14.05 -19.00   0.00   74
  3  ω   -103.00 -78.00   1.00   65.00    --  -14.36 178.00  60.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0596485000
_diffrn_orient_matrix_UB_12      -0.0250945000
_diffrn_orient_matrix_UB_13      -0.0171755000
_diffrn_orient_matrix_UB_21      0.0776505000
_diffrn_orient_matrix_UB_22      0.0184845000
_diffrn_orient_matrix_UB_23      0.0318776000
_diffrn_orient_matrix_UB_31      -0.0044842000
_diffrn_orient_matrix_UB_32      -0.0140685000
_diffrn_orient_matrix_UB_33      0.0725091000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2621
_reflns_number_total             3448
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.702
_refine_diff_density_min         -0.574
_refine_diff_density_rms         0.104
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         3448
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0658
_refine_ls_R_factor_gt           0.0445
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0541P)²+1.1979P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1106
_refine_ls_wR_factor_ref         0.1241
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N2-H2
 0.9 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B)
3.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17)
3.c Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.32277(5) 0.46435(2) 0.49165(4) 0.01896(13) Uani 1 1 d . . . . .
O1 O 0.1410(3) 0.45272(10) 0.6327(2) 0.0213(5) Uani 1 1 d . . . . .
O2 O 0.5024(3) 0.48879(11) 0.3621(2) 0.0224(5) Uani 1 1 d . . . . .
O11 O -0.0167(4) 0.38428(13) 0.7572(3) 0.0360(6) Uani 1 1 d . . . . .
N1 N 0.3390(3) 0.35620(12) 0.5386(3) 0.0165(5) Uani 1 1 d . . . . .
N2 N 0.1444(4) 0.45879(13) 0.2927(3) 0.0193(5) Uani 1 1 d D . . . .
H2 H 0.088(5) 0.4957(12) 0.286(4) 0.028(10) Uiso 1 1 d D . . . .
C10 C 0.4343(4) 0.30781(14) 0.4793(3) 0.0169(6) Uani 1 1 d . . . . .
C11 C 0.5943(4) 0.32342(16) 0.4146(4) 0.0234(7) Uani 1 1 d . . . . .
H11 H 0.633138 0.366043 0.411467 0.028 Uiso 1 1 calc R . . . .
C12 C 0.6919(5) 0.27533(17) 0.3565(4) 0.0276(7) Uani 1 1 d . . . . .
H12 H 0.797445 0.285821 0.314269 0.033 Uiso 1 1 calc R . . . .
C13 C 0.6371(5) 0.21093(17) 0.3591(4) 0.0272(7) Uani 1 1 d . . . . .
H13 H 0.706824 0.179103 0.320064 0.033 Uiso 1 1 calc R . . . .
C14 C 0.4815(5) 0.19461(16) 0.4187(3) 0.0248(7) Uani 1 1 d . . . . .
H14 H 0.444404 0.151714 0.418418 0.030 Uiso 1 1 calc R . . . .
C15 C 0.3759(4) 0.24242(15) 0.4811(3) 0.0187(6) Uani 1 1 d . . . . .
C16 C 0.2137(5) 0.22908(16) 0.5452(4) 0.0262(7) Uani 1 1 d . . . . .
H16 H 0.167190 0.187310 0.543906 0.031 Uiso 1 1 calc R . . . .
C17 C 0.1258(4) 0.27787(16) 0.6091(4) 0.0241(7) Uani 1 1 d . . . . .
H17 H 0.021804 0.269406 0.655371 0.029 Uiso 1 1 calc R . . . .
C18 C 0.1937(4) 0.34078(15) 0.6044(3) 0.0182(6) Uani 1 1 d . . . . .
C19 C 0.0965(4) 0.39652(16) 0.6710(3) 0.0203(6) Uani 1 1 d . . . . .
C21 C 0.2634(5) 0.45967(17) 0.1695(4) 0.0255(7) Uani 1 1 d . . . . .
H21A H 0.191870 0.472795 0.073612 0.031 Uiso 1 1 calc R . . . .
H21B H 0.313231 0.417007 0.156461 0.031 Uiso 1 1 calc R . . . .
C22 C 0.4186(5) 0.50707(17) 0.2158(3) 0.0250(7) Uani 1 1 d . . . . .
H22A H 0.507430 0.505572 0.144114 0.030 Uiso 1 1 calc R . . . .
H22B H 0.370433 0.550599 0.217612 0.030 Uiso 1 1 calc R . . . .
C23 C 0.0052(4) 0.40753(16) 0.2756(3) 0.0227(7) Uani 1 1 d . . . . .
H23A H -0.059180 0.407940 0.364293 0.027 Uiso 1 1 calc R . . . .
H23B H 0.067518 0.366299 0.274031 0.027 Uiso 1 1 calc R . . . .
C24 C -0.1355(5) 0.41295(19) 0.1337(4) 0.0302(8) Uani 1 1 d . . . . .
H24A H -0.074832 0.408347 0.044830 0.045 Uiso 1 1 calc GR . . . .
H24B H -0.194589 0.454337 0.131725 0.045 Uiso 1 1 calc GR . . . .
H24C H -0.226495 0.379615 0.134183 0.045 Uiso 1 1 calc GR . . . .


_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 Cu1 2.9694(7) 3_666 ?
Cu1 O1 1.962(2) . ?
Cu1 O2 1.945(2) 3_666 ?
Cu1 O2 1.929(2) . ?
Cu1 N1 2.281(2) . ?
Cu1 N2 2.039(3) . ?
O1 C19 1.269(4) . ?
O2 C22 1.402(4) . ?
O11 C19 1.229(4) . ?
N1 C10 1.368(4) . ?
N1 C18 1.321(4) . ?
N2 C21 1.487(4) . ?
N2 C23 1.465(4) . ?
C10 C11 1.411(4) . ?
C10 C15 1.423(4) . ?
C11 C12 1.368(4) . ?
C12 C13 1.395(5) . ?
C13 C14 1.362(5) . ?
C14 C15 1.416(4) . ?
C15 C16 1.412(4) . ?
C16 C17 1.363(5) . ?
C17 C18 1.399(4) . ?
C18 C19 1.519(4) . ?
C21 C22 1.513(5) . ?
C23 C24 1.509(5) . ?

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 Cu1 Cu1 134.01(7) . 3_666 ?
O1 Cu1 N1 77.64(9) . . ?
O1 Cu1 N2 97.66(10) . . ?
O2 Cu1 Cu1 40.15(6) . 3_666 ?
O2 Cu1 Cu1 39.77(6) 3_666 3_666 ?
O2 Cu1 O1 94.55(9) 3_666 . ?
O2 Cu1 O1 171.64(9) . . ?
O2 Cu1 O2 79.91(9) . 3_666 ?
O2 Cu1 N1 110.98(10) 3_666 . ?
O2 Cu1 N1 110.13(9) . . ?
O2 Cu1 N2 84.76(10) . . ?
O2 Cu1 N2 151.84(10) 3_666 . ?
N1 Cu1 Cu1 117.26(6) . 3_666 ?
N2 Cu1 Cu1 121.20(8) . 3_666 ?
N2 Cu1 N1 96.42(10) . . ?
C19 O1 Cu1 120.35(19) . . ?
Cu1 O2 Cu1 100.09(9) . 3_666 ?
C22 O2 Cu1 129.6(2) . 3_666 ?
C22 O2 Cu1 111.93(19) . . ?
C10 N1 Cu1 131.88(19) . . ?
C18 N1 Cu1 107.08(19) . . ?
C18 N1 C10 118.5(3) . . ?
C21 N2 Cu1 105.18(19) . . ?
C23 N2 Cu1 118.7(2) . . ?
C23 N2 C21 113.8(2) . . ?
N1 C10 C11 119.0(3) . . ?
N1 C10 C15 121.6(3) . . ?
C11 C10 C15 119.4(3) . . ?
C12 C11 C10 119.4(3) . . ?
C11 C12 C13 121.7(3) . . ?
C14 C13 C12 120.1(3) . . ?
C13 C14 C15 120.6(3) . . ?
C14 C15 C10 118.8(3) . . ?
C16 C15 C10 117.5(3) . . ?
C16 C15 C14 123.7(3) . . ?
C17 C16 C15 119.5(3) . . ?
C16 C17 C18 119.3(3) . . ?
N1 C18 C17 123.4(3) . . ?
N1 C18 C19 115.9(3) . . ?
C17 C18 C19 120.7(3) . . ?
O1 C19 C18 116.3(2) . . ?
O11 C19 O1 125.2(3) . . ?
O11 C19 C18 118.5(3) . . ?
N2 C21 C22 107.7(3) . . ?
O2 C22 C21 106.6(3) . . ?
N2 C23 C24 114.4(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 O1 0.869(18) 2.19(3) 2.924(3) 142(3) 3_566 yes

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.271
_oxdiff_exptl_absorpt_empirical_full_min 0.763
####################################################################### 
# 
# 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_syn-8d
_database_code_depnum_ccdc_archive 'CCDC 2077003'
loop_
_audit_author_name
_audit_author_address
'Barbara Modec'
;University of Ljubljana
Slovenia
;
_audit_update_record             
;
2021-04-12 deposited with the CCDC.	2022-03-18 downloaded from the CCDC.
;
_audit_creation_date             2021-03-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H28 Cu2 N4 O6'
_chemical_formula_sum            'C26 H28 Cu2 N4 O6'
_chemical_formula_weight         619.60
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   9.6201(6)
_cell_length_b                   23.1763(18)
_cell_length_c                   11.8397(11)
_cell_angle_alpha                90
_cell_angle_beta                 99.147(7)
_cell_angle_gamma                90
_cell_volume                     2606.2(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1969
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      29.3940
_cell_measurement_theta_min      3.0890
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.487
_exptl_absorpt_coefficient_mu    1.681
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.81485
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.579
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             1272
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0701
_diffrn_reflns_av_unetI/netI     0.1014
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7957
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.496
_diffrn_reflns_theta_min         3.089
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -15.00  56.00   1.00  150.00    --   14.05 -99.00  60.00   71
  2  ω    -16.00  59.00   1.00  150.00    --   14.05  57.00-150.00   75
  3  ω    -89.00  12.00   1.00  150.00    --  -14.36 -37.00-120.00  101
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0188580000
_diffrn_orient_matrix_UB_12      -0.0274617000
_diffrn_orient_matrix_UB_13      -0.0240744000
_diffrn_orient_matrix_UB_21      0.0035766000
_diffrn_orient_matrix_UB_22      0.0110794000
_diffrn_orient_matrix_UB_23      -0.0553229000
_diffrn_orient_matrix_UB_31      0.0721658000
_diffrn_orient_matrix_UB_32      -0.0077449000
_diffrn_orient_matrix_UB_33      0.0064396000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2011
_reflns_number_total             3010
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.012
_refine_diff_density_min         -0.650
_refine_diff_density_rms         0.106
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         3010
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0571
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0391P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1049
_refine_ls_wR_factor_ref         0.1214
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C21(H21)
2.b Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17)
2.d Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.59702(5) 0.59419(2) 0.49130(4) 0.02375(18) Uani 1 1 d . . . . .
O1 O 0.4672(3) 0.57171(13) 0.5963(2) 0.0286(7) Uani 1 1 d . . . . .
O2 O 0.7356(3) 0.60565(12) 0.3908(2) 0.0288(7) Uani 1 1 d . . . . .
O11 O 0.3016(3) 0.60176(12) 0.6952(2) 0.0292(7) Uani 1 1 d . . . . .
N1 N 0.4973(3) 0.67866(14) 0.5179(3) 0.0199(7) Uani 1 1 d . . . . .
N2 N 0.4858(3) 0.55364(15) 0.3573(3) 0.0269(8) Uani 1 1 d . . . . .
H2A H 0.486707 0.515764 0.369828 0.032 Uiso 1 1 calc R . . . .
H2B H 0.396767 0.565638 0.347256 0.032 Uiso 1 1 calc R . . . .
C10 C 0.5221(4) 0.73359(18) 0.4822(4) 0.0217(9) Uani 1 1 d . . . . .
C11 C 0.6098(4) 0.74169(18) 0.3987(4) 0.0257(10) Uani 1 1 d . . . . .
H11 H 0.651616 0.709984 0.369666 0.031 Uiso 1 1 calc R . . . .
C12 C 0.6335(4) 0.7954(2) 0.3606(4) 0.0331(11) Uani 1 1 d . . . . .
H12 H 0.692340 0.800088 0.306152 0.040 Uiso 1 1 calc R . . . .
C13 C 0.5710(4) 0.8436(2) 0.4017(4) 0.0348(11) Uani 1 1 d . . . . .
H13 H 0.586818 0.880123 0.373575 0.042 Uiso 1 1 calc R . . . .
C14 C 0.4862(4) 0.8373(2) 0.4839(4) 0.0354(11) Uani 1 1 d . . . . .
H14 H 0.445527 0.869666 0.511634 0.042 Uiso 1 1 calc R . . . .
C15 C 0.4601(4) 0.78243(18) 0.5264(4) 0.0239(9) Uani 1 1 d . . . . .
C16 C 0.3737(4) 0.7727(2) 0.6112(4) 0.0324(11) Uani 1 1 d . . . . .
H16 H 0.334442 0.803773 0.644506 0.039 Uiso 1 1 calc R . . . .
C17 C 0.3487(4) 0.71877(19) 0.6432(4) 0.0293(10) Uani 1 1 d . . . . .
H17 H 0.288883 0.712084 0.696299 0.035 Uiso 1 1 calc R . . . .
C18 C 0.4138(4) 0.67246(18) 0.5959(3) 0.0206(9) Uani 1 1 d . . . . .
C19 C 0.3898(4) 0.61055(19) 0.6321(4) 0.0238(10) Uani 1 1 d . . . . .
C21 C 0.5488(5) 0.5664(2) 0.2549(4) 0.0434(13) Uani 1 1 d . . . . .
H21 H 0.516068 0.604788 0.228004 0.052 Uiso 1 1 calc R . . . .
C22 C 0.7036(4) 0.5702(2) 0.2921(4) 0.0409(13) Uani 1 1 d . . . . .
H22A H 0.741604 0.531868 0.308999 0.049 Uiso 1 1 calc R . . . .
H22B H 0.747269 0.586178 0.230575 0.049 Uiso 1 1 calc R . . . .
C23 C 0.5065(5) 0.5251(2) 0.1581(4) 0.0428(13) Uani 1 1 d . . . . .
H23A H 0.533754 0.486673 0.182668 0.064 Uiso 1 1 calc GR . . . .
H23B H 0.552455 0.535548 0.094788 0.064 Uiso 1 1 calc GR . . . .
H23C H 0.406342 0.526600 0.134964 0.064 Uiso 1 1 calc GR . . . .


_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 Cu1 2.9177(9) 2_656 ?
Cu1 O1 1.967(3) . ?
Cu1 O2 1.941(3) . ?
Cu1 O2 1.974(3) 2_656 ?
Cu1 N1 2.225(3) . ?
Cu1 N2 2.001(3) . ?
O1 C19 1.283(5) . ?
O2 C22 1.422(5) . ?
O11 C19 1.233(4) . ?
N1 C10 1.374(5) . ?
N1 C18 1.325(5) . ?
N2 C21 1.470(6) . ?
C10 C11 1.410(5) . ?
C10 C15 1.417(5) . ?
C11 C12 1.355(6) . ?
C12 C13 1.393(6) . ?
C13 C14 1.373(6) . ?
C14 C15 1.405(6) . ?
C15 C16 1.420(5) . ?
C16 C17 1.339(6) . ?
C17 C18 1.404(6) . ?
C18 C19 1.526(6) . ?
C21 C22 1.486(6) . ?
C21 C23 1.499(6) . ?

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 Cu1 Cu1 133.63(9) . 2_656 ?
O1 Cu1 O2 96.74(12) . 2_656 ?
O1 Cu1 N1 79.18(12) . . ?
O1 Cu1 N2 93.62(13) . . ?
O2 Cu1 Cu1 41.38(8) 2_656 2_656 ?
O2 Cu1 Cu1 42.26(9) . 2_656 ?
O2 Cu1 O1 172.07(12) . . ?
O2 Cu1 O2 81.51(13) . 2_656 ?
O2 Cu1 N1 108.66(12) . . ?
O2 Cu1 N1 95.92(11) 2_656 . ?
O2 Cu1 N2 153.76(13) 2_656 . ?
O2 Cu1 N2 84.91(12) . . ?
N1 Cu1 Cu1 116.29(7) . 2_656 ?
N2 Cu1 Cu1 117.54(9) . 2_656 ?
N2 Cu1 N1 109.70(13) . . ?
C19 O1 Cu1 118.9(3) . . ?
Cu1 O2 Cu1 96.36(13) . 2_656 ?
C22 O2 Cu1 110.2(2) . . ?
C22 O2 Cu1 123.3(3) . 2_656 ?
C10 N1 Cu1 132.2(2) . . ?
C18 N1 Cu1 109.0(3) . . ?
C18 N1 C10 118.0(3) . . ?
C21 N2 Cu1 108.7(3) . . ?
N1 C10 C11 119.4(4) . . ?
N1 C10 C15 121.5(4) . . ?
C11 C10 C15 119.1(4) . . ?
C12 C11 C10 120.4(4) . . ?
C11 C12 C13 121.1(4) . . ?
C14 C13 C12 119.9(4) . . ?
C13 C14 C15 120.7(4) . . ?
C10 C15 C16 117.5(4) . . ?
C14 C15 C10 118.8(4) . . ?
C14 C15 C16 123.7(4) . . ?
C17 C16 C15 120.1(4) . . ?
C16 C17 C18 119.3(4) . . ?
N1 C18 C17 123.6(4) . . ?
N1 C18 C19 115.7(4) . . ?
C17 C18 C19 120.7(3) . . ?
O1 C19 C18 116.4(3) . . ?
O11 C19 O1 125.2(4) . . ?
O11 C19 C18 118.4(4) . . ?
N2 C21 C22 107.0(4) . . ?
N2 C21 C23 113.9(4) . . ?
C22 C21 C23 113.7(4) . . ?
O2 C22 C21 110.7(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
_geom_hbond_publ_flag
N2 H2A O1 0.89 2.10 2.978(5) 168.5 5_666 yes
N2 H2B O11 0.89 2.07 2.954(4) 171.2 2_556 yes

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.990
_oxdiff_exptl_absorpt_empirical_full_min 0.496
####################################################################### 
# 
# 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_anti11d2MeOH2(3a1pOH)
_database_code_depnum_ccdc_archive 'CCDC 2077015'
loop_
_audit_author_name
_audit_author_address
'Barbara Modec'
;University of Ljubljana
Slovenia
;
_audit_update_record             
;
2021-04-12 deposited with the CCDC.	2022-03-18 downloaded from the CCDC.
;
_audit_creation_date             2021-03-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H28 Cu2 N4 O6, 2(C3 H9 N O), 2(C H4 O)'
_chemical_formula_sum            'C34 H54 Cu2 N6 O10'
_chemical_formula_weight         833.91
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.0521(4)
_cell_length_b                   12.0235(3)
_cell_length_c                   14.0783(6)
_cell_angle_alpha                90
_cell_angle_beta                 110.038(4)
_cell_angle_gamma                90
_cell_volume                     1916.57(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9487
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      30.1080
_cell_measurement_theta_min      3.3630
_shelx_estimated_absorpt_T_max   0.966
_shelx_estimated_absorpt_T_min   0.758
_exptl_absorpt_coefficient_mu    1.172
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76768
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.445
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             876
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0285
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.925
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            23793
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.925
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.323
_diffrn_reflns_theta_min         2.471
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -62.00  40.00   1.00   60.00    --   14.05 -37.00-180.00  102
  2  ω    -12.00  90.00   1.00   60.00    --   14.05  37.00 150.00  102
  3  ω    -15.00  56.00   1.00   60.00    --   14.05 -99.00 -30.00   71
  4  ω    -32.00  96.00   1.00   60.00    --   14.05  19.00 -90.00  128
  5  ω    -42.00  17.00   1.00   60.00    --  -14.36 -77.00 120.00   59
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0597087000
_diffrn_orient_matrix_UB_12      0.0170121000
_diffrn_orient_matrix_UB_13      0.0127742000
_diffrn_orient_matrix_UB_21      0.0011761000
_diffrn_orient_matrix_UB_22      0.0148999000
_diffrn_orient_matrix_UB_23      0.0490730000
_diffrn_orient_matrix_UB_31      0.0189833000
_diffrn_orient_matrix_UB_32      -0.0544842000
_diffrn_orient_matrix_UB_33      0.0174030000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4428
_reflns_number_total             5314
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.392
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     260
_refine_ls_number_reflns         5314
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0282
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0246P)²+0.8793P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0627
_refine_ls_wR_factor_ref         0.0677
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C31(H31A,H31B), C32(H32A,
 H32B), C33(H33A,H33B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17)
2.c Idealised Me refined as rotating group:
 C41(H41A,H41B,H41C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.57061(2) 0.39464(2) 0.54157(2) 0.01499(6) Uani 1 1 d . . . . .
O1 O 0.65517(10) 0.39140(8) 0.70949(8) 0.0221(2) Uani 1 1 d . . . . .
O2 O 0.57958(9) 0.53291(8) 0.47419(8) 0.0202(2) Uani 1 1 d . . . . .
O3 O 0.88257(11) 0.19492(11) 0.69643(10) 0.0313(3) Uani 1 1 d . . . . .
H3 H 0.9332(19) 0.1738(18) 0.6725(17) 0.040(6) Uiso 1 1 d . . . . .
O4 O 0.95121(12) 0.63143(12) 0.88204(11) 0.0374(3) Uani 1 1 d . . . . .
H4 H 0.933(2) 0.564(2) 0.879(2) 0.067(9) Uiso 1 1 d . . . . .
O11 O 0.66313(11) 0.28281(10) 0.84005(9) 0.0302(3) Uani 1 1 d . . . . .
N1 N 0.51791(10) 0.24419(9) 0.57840(9) 0.0160(2) Uani 1 1 d . . . . .
N2 N 0.71958(12) 0.33324(11) 0.53124(11) 0.0184(3) Uani 1 1 d . . . . .
H2A H 0.7027(16) 0.2988(15) 0.4780(15) 0.023(5) Uiso 1 1 d . . . . .
H2B H 0.7481(16) 0.2877(16) 0.5787(15) 0.027(5) Uiso 1 1 d . . . . .
N3 N 0.91398(16) 0.41397(14) 0.88621(16) 0.0392(4) Uani 1 1 d . . . . .
H3A H 0.928(2) 0.387(2) 0.950(2) 0.058(8) Uiso 1 1 d . . . . .
H3B H 0.848(3) 0.396(2) 0.847(2) 0.069(9) Uiso 1 1 d . . . . .
C10 C 0.44565(12) 0.17203(11) 0.50898(12) 0.0182(3) Uani 1 1 d . . . . .
C11 C 0.41964(14) 0.19181(13) 0.40536(12) 0.0232(3) Uani 1 1 d . . . . .
H11 H 0.450207 0.254278 0.384097 0.028 Uiso 1 1 calc R . . . .
C12 C 0.34945(15) 0.11940(14) 0.33566(14) 0.0290(4) Uani 1 1 d . . . . .
H12 H 0.333675 0.132349 0.267149 0.035 Uiso 1 1 calc R . . . .
C13 C 0.30065(14) 0.02522(14) 0.36644(15) 0.0317(4) Uani 1 1 d . . . . .
H13 H 0.252574 -0.023079 0.318180 0.038 Uiso 1 1 calc R . . . .
C14 C 0.32357(14) 0.00477(13) 0.46631(15) 0.0293(4) Uani 1 1 d . . . . .
H14 H 0.290612 -0.057270 0.485861 0.035 Uiso 1 1 calc R . . . .
C15 C 0.39733(13) 0.07719(12) 0.54104(13) 0.0220(3) Uani 1 1 d . . . . .
C16 C 0.42606(15) 0.05921(13) 0.64510(14) 0.0266(4) Uani 1 1 d . . . . .
H16 H 0.393998 -0.000989 0.668189 0.032 Uiso 1 1 calc R . . . .
C17 C 0.50136(15) 0.13048(12) 0.71252(13) 0.0239(3) Uani 1 1 d . . . . .
H17 H 0.522960 0.117863 0.781670 0.029 Uiso 1 1 calc R . . . .
C18 C 0.54580(13) 0.22312(12) 0.67611(12) 0.0184(3) Uani 1 1 d . . . . .
C19 C 0.62863(13) 0.30634(13) 0.74851(12) 0.0204(3) Uani 1 1 d . . . . .
C21 C 0.81313(14) 0.41412(13) 0.53534(13) 0.0256(3) Uani 1 1 d . . . . .
H21A H 0.880080 0.375212 0.527708 0.031 Uiso 1 1 calc R . . . .
H21B H 0.839473 0.450492 0.600803 0.031 Uiso 1 1 calc R . . . .
C22 C 0.76955(14) 0.50089(13) 0.45304(14) 0.0262(3) Uani 1 1 d . . . . .
H22A H 0.731049 0.463761 0.388999 0.031 Uiso 1 1 calc R . . . .
H22B H 0.836850 0.541271 0.447707 0.031 Uiso 1 1 calc R . . . .
C23 C 0.68367(14) 0.58333(13) 0.47182(15) 0.0267(4) Uani 1 1 d . . . . .
H23A H 0.722178 0.620718 0.535739 0.032 Uiso 1 1 calc R . . . .
H23B H 0.663415 0.639232 0.418948 0.032 Uiso 1 1 calc R . . . .
C31 C 1.00360(17) 0.36840(17) 0.84903(16) 0.0400(5) Uani 1 1 d . . . . .
H31A H 1.077740 0.405985 0.883487 0.048 Uiso 1 1 calc R . . . .
H31B H 0.981242 0.385766 0.777635 0.048 Uiso 1 1 calc R . . . .
C32 C 1.02420(16) 0.24400(18) 0.86215(15) 0.0396(5) Uani 1 1 d . . . . .
H32A H 1.091325 0.224575 0.842373 0.047 Uiso 1 1 calc R . . . .
H32B H 1.044413 0.225841 0.933215 0.047 Uiso 1 1 calc R . . . .
C33 C 0.91991(16) 0.17391(15) 0.80193(14) 0.0331(4) Uani 1 1 d . . . . .
H33A H 0.940815 0.095977 0.813947 0.040 Uiso 1 1 calc R . . . .
H33B H 0.854609 0.188292 0.825643 0.040 Uiso 1 1 calc R . . . .
C41 C 0.84384(19) 0.69109(19) 0.84747(19) 0.0497(5) Uani 1 1 d . . . . .
H41A H 0.791405 0.656630 0.787309 0.075 Uiso 1 1 calc GR . . . .
H41B H 0.859028 0.766373 0.832788 0.075 Uiso 1 1 calc GR . . . .
H41C H 0.808100 0.690807 0.898824 0.075 Uiso 1 1 calc GR . . . .


_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 Cu1 3.0530(3) 3_666 ?
Cu1 O1 2.2311(11) . ?
Cu1 O2 1.9353(10) . ?
Cu1 O2 1.9518(10) 3_666 ?
Cu1 N1 2.0422(12) . ?
Cu1 N2 1.9921(13) . ?
O1 C19 1.2532(19) . ?
O2 C23 1.4040(17) . ?
O3 C33 1.419(2) . ?
O4 C41 1.412(2) . ?
O11 C19 1.2437(19) . ?
N1 C10 1.3723(19) . ?
N1 C18 1.3238(19) . ?
N2 C21 1.475(2) . ?
N3 C31 1.459(3) . ?
C10 C11 1.403(2) . ?
C10 C15 1.422(2) . ?
C11 C12 1.367(2) . ?
C12 C13 1.411(3) . ?
C13 C14 1.359(3) . ?
C14 C15 1.419(2) . ?
C15 C16 1.402(2) . ?
C16 C17 1.367(3) . ?
C17 C18 1.407(2) . ?
C18 C19 1.529(2) . ?
C21 C22 1.513(2) . ?
C22 C23 1.520(2) . ?
C31 C32 1.517(3) . ?
C32 C33 1.509(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 Cu1 114.39(3) . 3_666 ?
O2 Cu1 Cu1 38.43(3) . 3_666 ?
O2 Cu1 Cu1 38.05(3) 3_666 3_666 ?
O2 Cu1 O1 116.90(4) . . ?
O2 Cu1 O1 101.38(4) 3_666 . ?
O2 Cu1 O2 76.48(5) . 3_666 ?
O2 Cu1 N1 163.70(5) . . ?
O2 Cu1 N1 93.85(4) 3_666 . ?
O2 Cu1 N2 168.82(5) 3_666 . ?
O2 Cu1 N2 94.56(5) . . ?
N1 Cu1 Cu1 130.65(3) . 3_666 ?
N1 Cu1 O1 77.55(4) . . ?
N2 Cu1 Cu1 132.65(4) . 3_666 ?
N2 Cu1 O1 88.57(5) . . ?
N2 Cu1 N1 93.26(5) . . ?
C19 O1 Cu1 112.72(10) . . ?
Cu1 O2 Cu1 103.52(5) . 3_666 ?
C23 O2 Cu1 125.66(9) . . ?
C23 O2 Cu1 127.30(9) . 3_666 ?
C10 N1 Cu1 123.77(10) . . ?
C18 N1 Cu1 116.30(10) . . ?
C18 N1 C10 119.50(12) . . ?
C21 N2 Cu1 116.66(10) . . ?
N1 C10 C11 119.63(13) . . ?
N1 C10 C15 120.64(14) . . ?
C11 C10 C15 119.73(14) . . ?
C12 C11 C10 120.08(15) . . ?
C11 C12 C13 120.75(17) . . ?
C14 C13 C12 120.31(16) . . ?
C13 C14 C15 120.63(15) . . ?
C14 C15 C10 118.50(15) . . ?
C16 C15 C10 118.29(14) . . ?
C16 C15 C14 123.21(15) . . ?
C17 C16 C15 119.76(14) . . ?
C16 C17 C18 119.25(15) . . ?
N1 C18 C17 122.50(14) . . ?
N1 C18 C19 116.28(13) . . ?
C17 C18 C19 121.22(14) . . ?
O1 C19 C18 116.62(13) . . ?
O11 C19 O1 126.51(15) . . ?
O11 C19 C18 116.87(14) . . ?
N2 C21 C22 111.38(13) . . ?
C21 C22 C23 113.25(14) . . ?
O2 C23 C22 112.94(12) . . ?
N3 C31 C32 115.91(17) . . ?
C33 C32 C31 114.33(16) . . ?
O3 C33 C32 113.13(16) . . ?

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
_geom_hbond_publ_flag
O3 H3 O4 0.83(2) 1.88(2) 2.708(2) 178(2) 2_746 yes
O4 H4 N3 0.84(3) 1.83(3) 2.657(2) 172(3) . yes
N2 H2A O11 0.818(19) 2.08(2) 2.8982(18) 177.4(18) 4_565 yes
N2 H2B O3 0.84(2) 2.19(2) 2.9837(18) 158.5(17) . yes

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.587
_oxdiff_exptl_absorpt_empirical_full_min 0.635

#===END
####################################################################### 
# 
# 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_11a3a1pOH
_database_code_depnum_ccdc_archive 'CCDC 2077008'
loop_
_audit_author_name
_audit_author_address
'Barbara Modec'
;University of Ljubljana
Slovenia
;
_audit_update_record             
;
2021-04-12 deposited with the CCDC.	2022-03-18 downloaded from the CCDC.
;
_audit_creation_date             2021-03-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C13 H15 Cu0.5 N2 O3), C3 H9 N O'
_chemical_formula_sum            'C29 H39 Cu N5 O7'
_chemical_formula_weight         633.19
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4853(3)
_cell_length_b                   14.1745(6)
_cell_length_c                   14.3105(6)
_cell_angle_alpha                88.622(3)
_cell_angle_beta                 76.298(4)
_cell_angle_gamma                82.897(3)
_cell_volume                     1463.80(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7184
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      30.0990
_cell_measurement_theta_min      2.8310
_shelx_estimated_absorpt_T_max   0.825
_shelx_estimated_absorpt_T_min   0.690
_exptl_absorpt_coefficient_mu    0.801
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.72634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.437
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             666
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.25
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.863
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            13494
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.863
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.285
_diffrn_reflns_theta_min         2.822
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.863
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -41.00  48.00   1.00    4.00    --   14.21 -77.00 120.00   89
  2  ω     -6.00  24.00   1.00    4.00    --  -14.52 -91.00 -14.00   30
  3  ω    -38.00 -12.00   1.00    4.00    --  -14.52  77.00 150.00   26
  4  ω    -36.00  57.00   1.00    4.00    --  -14.52  57.00   0.00   93
  5  ω    -88.00  15.00   1.00    4.00    --  -14.52 -57.00-150.00  103
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0204618000
_diffrn_orient_matrix_UB_12      -0.0341386000
_diffrn_orient_matrix_UB_13      0.0368218000
_diffrn_orient_matrix_UB_21      0.0776610000
_diffrn_orient_matrix_UB_22      -0.0312936000
_diffrn_orient_matrix_UB_23      -0.0242395000
_diffrn_orient_matrix_UB_31      0.0566182000
_diffrn_orient_matrix_UB_32      0.0199571000
_diffrn_orient_matrix_UB_33      0.0256790000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6185
_reflns_number_total             7569
_reflns_odcompleteness_completeness 99.91
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.548
_refine_diff_density_min         -0.541
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     418
_refine_ls_number_reflns         7569
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0379
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0480P)²+0.8229P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0951
_refine_ls_wR_factor_ref         0.1047
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 O5-H5
 0.87 with sigma of 0.01
 N5-H5B = N5-H5A
 0.89 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C41(H41A,H41B), C42(H42A,
 H42B), C43(H43A,H43B), C51(H51A,H51B), C52(H52A,H52B), C53(H53A,H53B)
3.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17), C31(H31),
 C32(H32), C33(H33), C34(H34), C36(H36), C37(H37)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.500000 0.500000 0.000000 0.01401(8) Uani 1 2 d S T P . .
Cu2 Cu 0.500000 1.000000 0.500000 0.01490(8) Uani 1 2 d S T P . .
O1 O 0.69652(16) 0.56225(9) 0.04168(9) 0.0176(3) Uani 1 1 d . . . . .
O2 O 0.0513(2) 0.73454(14) 0.40706(13) 0.0408(4) Uani 1 1 d . . . . .
H2 H 0.064(4) 0.775(2) 0.434(2) 0.055(10) Uiso 1 1 d . . . . .
O3 O 0.29997(16) 0.92678(9) 0.47670(9) 0.0177(3) Uani 1 1 d . . . . .
O4 O 0.7438(3) 0.61586(12) 0.71299(13) 0.0412(4) Uani 1 1 d . . . . .
H4 H 0.848(3) 0.6228(18) 0.6852(18) 0.028(7) Uiso 1 1 d . . . . .
O5 O -0.3133(2) 0.70037(12) 0.43593(13) 0.0405(4) Uani 1 1 d D . . . .
H5 H -0.1958(19) 0.710(3) 0.421(3) 0.079(12) Uiso 1 1 d D . . . .
O11 O 0.92764(18) 0.54964(10) 0.11686(11) 0.0266(3) Uani 1 1 d . . . . .
O33 O 0.02430(17) 0.87678(10) 0.53195(10) 0.0231(3) Uani 1 1 d . . . . .
N1 N 0.6718(2) 0.37369(11) 0.06327(11) 0.0170(3) Uani 1 1 d . . . . .
N2 N 0.3207(2) 0.52639(11) 0.12949(11) 0.0165(3) Uani 1 1 d . . . . .
H2A H 0.210(3) 0.5312(17) 0.1179(17) 0.025(6) Uiso 1 1 d . . . . .
H2B H 0.328(3) 0.4776(16) 0.1647(15) 0.015(5) Uiso 1 1 d . . . . .
N3 N 0.2502(2) 1.03375(11) 0.63796(11) 0.0161(3) Uani 1 1 d . . . . .
N4 N 0.6111(2) 0.88115(12) 0.55581(12) 0.0185(3) Uani 1 1 d . . . . .
H4A H 0.729(3) 0.8870(17) 0.5427(17) 0.027(6) Uiso 1 1 d . . . . .
H4B H 0.595(3) 0.8340(19) 0.5217(18) 0.029(6) Uiso 1 1 d . . . . .
N5 N -0.1018(3) 0.36057(17) 0.3966(2) 0.0495(6) Uani 1 1 d D . . . .
H5A H -0.128(5) 0.3037(15) 0.381(3) 0.095(14) Uiso 1 1 d D . . . .
H5B H -0.086(6) 0.375(3) 0.4550(16) 0.115(17) Uiso 1 1 d D . . . .
C10 C 0.6619(3) 0.27778(13) 0.07014(13) 0.0193(4) Uani 1 1 d . . . . .
C11 C 0.5215(3) 0.24058(15) 0.03640(14) 0.0254(4) Uani 1 1 d . . . . .
H11 H 0.436723 0.280970 0.011474 0.030 Uiso 1 1 calc R . . . .
C12 C 0.5113(3) 0.14432(16) 0.04077(16) 0.0338(5) Uani 1 1 d . . . . .
H12 H 0.419928 0.119720 0.018036 0.041 Uiso 1 1 calc R . . . .
C13 C 0.6373(4) 0.08272(16) 0.07919(17) 0.0378(5) Uani 1 1 d . . . . .
H13 H 0.628384 0.017803 0.081743 0.045 Uiso 1 1 calc R . . . .
C14 C 0.7726(3) 0.11719(15) 0.11277(16) 0.0330(5) Uani 1 1 d . . . . .
H14 H 0.854190 0.075627 0.138670 0.040 Uiso 1 1 calc R . . . .
C15 C 0.7902(3) 0.21568(14) 0.10861(14) 0.0243(4) Uani 1 1 d . . . . .
C16 C 0.9289(3) 0.25607(15) 0.14007(15) 0.0276(4) Uani 1 1 d . . . . .
H16 H 1.014513 0.217474 0.166062 0.033 Uiso 1 1 calc R . . . .
C17 C 0.9378(3) 0.35143(15) 0.13253(14) 0.0250(4) Uani 1 1 d . . . . .
H17 H 1.029241 0.378583 0.152773 0.030 Uiso 1 1 calc R . . . .
C18 C 0.8044(2) 0.40843(13) 0.09308(13) 0.0181(3) Uani 1 1 d . . . . .
C19 C 0.8115(2) 0.51564(13) 0.08349(13) 0.0182(3) Uani 1 1 d . . . . .
C21 C 0.3368(3) 0.61117(13) 0.18373(13) 0.0207(4) Uani 1 1 d . . . . .
H21A H 0.334545 0.666281 0.142318 0.025 Uiso 1 1 calc R . . . .
H21B H 0.455501 0.602896 0.200970 0.025 Uiso 1 1 calc R . . . .
C22 C 0.1847(3) 0.63007(14) 0.27419(14) 0.0231(4) Uani 1 1 d . . . . .
H22A H 0.187044 0.575409 0.316171 0.028 Uiso 1 1 calc R . . . .
H22B H 0.065576 0.638508 0.257355 0.028 Uiso 1 1 calc R . . . .
C23 C 0.2055(3) 0.71752(14) 0.32742(14) 0.0242(4) Uani 1 1 d . . . . .
H23A H 0.319229 0.707691 0.349520 0.029 Uiso 1 1 calc R . . . .
H23B H 0.210987 0.771937 0.284869 0.029 Uiso 1 1 calc R . . . .
C30 C 0.2233(2) 1.09100(13) 0.71696(13) 0.0173(3) Uani 1 1 d . . . . .
C31 C 0.3707(3) 1.13945(15) 0.72944(14) 0.0241(4) Uani 1 1 d . . . . .
H31 H 0.484547 1.130984 0.685178 0.029 Uiso 1 1 calc R . . . .
C32 C 0.3450(3) 1.19871(15) 0.80670(15) 0.0285(4) Uani 1 1 d . . . . .
H32 H 0.442554 1.230022 0.814674 0.034 Uiso 1 1 calc R . . . .
C33 C 0.1737(3) 1.21318(15) 0.87443(15) 0.0296(4) Uani 1 1 d . . . . .
H33 H 0.158022 1.254926 0.925682 0.036 Uiso 1 1 calc R . . . .
C34 C 0.0304(3) 1.16608(15) 0.86503(14) 0.0250(4) Uani 1 1 d . . . . .
H34 H -0.081715 1.175144 0.910642 0.030 Uiso 1 1 calc R . . . .
C35 C 0.0510(2) 1.10348(13) 0.78643(13) 0.0189(4) Uani 1 1 d . . . . .
C36 C -0.0912(2) 1.05323(14) 0.77214(13) 0.0218(4) Uani 1 1 d . . . . .
H36 H -0.205125 1.059029 0.816452 0.026 Uiso 1 1 calc R . . . .
C37 C -0.0621(2) 0.99605(14) 0.69339(14) 0.0210(4) Uani 1 1 d . . . . .
H37 H -0.155308 0.962592 0.683299 0.025 Uiso 1 1 calc R . . . .
C38 C 0.1129(2) 0.98865(12) 0.62725(12) 0.0159(3) Uani 1 1 d . . . . .
C39 C 0.1484(2) 0.92565(12) 0.53842(13) 0.0161(3) Uani 1 1 d . . . . .
C41 C 0.5423(3) 0.86470(14) 0.66019(14) 0.0228(4) Uani 1 1 d . . . . .
H41A H 0.416732 0.848603 0.671755 0.027 Uiso 1 1 calc R . . . .
H41B H 0.538347 0.923270 0.694718 0.027 Uiso 1 1 calc R . . . .
C42 C 0.6607(3) 0.78574(15) 0.70044(15) 0.0250(4) Uani 1 1 d . . . . .
H42A H 0.790398 0.791102 0.672597 0.030 Uiso 1 1 calc R . . . .
H42B H 0.638772 0.794528 0.769417 0.030 Uiso 1 1 calc R . . . .
C43 C 0.6214(3) 0.68751(15) 0.68065(16) 0.0309(5) Uani 1 1 d . . . . .
H43A H 0.494594 0.679933 0.712842 0.037 Uiso 1 1 calc R . . . .
H43B H 0.634661 0.679842 0.612085 0.037 Uiso 1 1 calc R . . . .
C51 C -0.2426(4) 0.43837(19) 0.3825(2) 0.0426(6) Uani 1 1 d . . . . .
H51A H -0.365169 0.420498 0.409745 0.051 Uiso 1 1 calc R . . . .
H51B H -0.230994 0.448825 0.314150 0.051 Uiso 1 1 calc R . . . .
C52 C -0.2210(3) 0.52875(17) 0.42919(17) 0.0326(5) Uani 1 1 d . . . . .
H52A H -0.091296 0.538463 0.413939 0.039 Uiso 1 1 calc R . . . .
H52B H -0.261976 0.523393 0.498475 0.039 Uiso 1 1 calc R . . . .
C53 C -0.3334(3) 0.61372(17) 0.39485(18) 0.0358(5) Uani 1 1 d . . . . .
H53A H -0.294225 0.617720 0.325375 0.043 Uiso 1 1 calc R . . . .
H53B H -0.463206 0.604090 0.411171 0.043 Uiso 1 1 calc R . . . .


_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 O1 2.0149(12) 2_665 ?
Cu1 O1 2.0149(12) . ?
Cu1 N1 2.3627(15) . ?
Cu1 N1 2.3627(15) 2_665 ?
Cu1 N2 2.0263(15) 2_665 ?
Cu1 N2 2.0263(15) . ?
Cu2 O3 2.0168(12) . ?
Cu2 O3 2.0168(12) 2_676 ?
Cu2 N3 2.3869(15) . ?
Cu2 N3 2.3869(15) 2_676 ?
Cu2 N4 2.0177(16) 2_676 ?
Cu2 N4 2.0177(16) . ?
O1 C19 1.273(2) . ?
O2 C23 1.418(2) . ?
O3 C39 1.263(2) . ?
O4 C43 1.426(3) . ?
O5 C53 1.414(3) . ?
O11 C19 1.236(2) . ?
O33 C39 1.247(2) . ?
N1 C10 1.370(2) . ?
N1 C18 1.320(2) . ?
N2 C21 1.479(2) . ?
N3 C30 1.369(2) . ?
N3 C38 1.316(2) . ?
N4 C41 1.483(2) . ?
N5 C51 1.474(3) . ?
C10 C11 1.416(3) . ?
C10 C15 1.421(3) . ?
C11 C12 1.375(3) . ?
C12 C13 1.405(3) . ?
C13 C14 1.364(3) . ?
C14 C15 1.417(3) . ?
C15 C16 1.410(3) . ?
C16 C17 1.362(3) . ?
C17 C18 1.419(2) . ?
C18 C19 1.529(3) . ?
C21 C22 1.512(3) . ?
C22 C23 1.513(3) . ?
C30 C31 1.416(3) . ?
C30 C35 1.424(2) . ?
C31 C32 1.367(3) . ?
C32 C33 1.408(3) . ?
C33 C34 1.365(3) . ?
C34 C35 1.417(3) . ?
C35 C36 1.407(3) . ?
C36 C37 1.363(3) . ?
C37 C38 1.417(2) . ?
C38 C39 1.523(2) . ?
C41 C42 1.528(3) . ?
C42 C43 1.505(3) . ?
C51 C52 1.503(3) . ?
C52 C53 1.522(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 180.0 2_665 . ?
O1 Cu1 N1 104.06(5) . 2_665 ?
O1 Cu1 N1 104.06(5) 2_665 . ?
O1 Cu1 N1 75.94(5) . . ?
O1 Cu1 N1 75.94(5) 2_665 2_665 ?
O1 Cu1 N2 91.64(6) 2_665 2_665 ?
O1 Cu1 N2 88.36(6) . 2_665 ?
O1 Cu1 N2 88.36(6) 2_665 . ?
O1 Cu1 N2 91.64(6) . . ?
N1 Cu1 N1 180.0 . 2_665 ?
N2 Cu1 N1 88.13(6) 2_665 . ?
N2 Cu1 N1 88.13(6) . 2_665 ?
N2 Cu1 N1 91.87(6) . . ?
N2 Cu1 N1 91.87(6) 2_665 2_665 ?
N2 Cu1 N2 180.0 2_665 . ?
O3 Cu2 O3 180.00(7) . 2_676 ?
O3 Cu2 N3 75.69(5) 2_676 2_676 ?
O3 Cu2 N3 104.32(5) 2_676 . ?
O3 Cu2 N3 75.68(5) . . ?
O3 Cu2 N3 104.31(5) . 2_676 ?
O3 Cu2 N4 88.78(6) . . ?
O3 Cu2 N4 91.22(6) . 2_676 ?
O3 Cu2 N4 88.78(6) 2_676 2_676 ?
O3 Cu2 N4 91.22(6) 2_676 . ?
N3 Cu2 N3 180.0 . 2_676 ?
N4 Cu2 N3 94.54(6) . . ?
N4 Cu2 N3 85.46(6) . 2_676 ?
N4 Cu2 N3 85.46(6) 2_676 . ?
N4 Cu2 N3 94.54(6) 2_676 2_676 ?
N4 Cu2 N4 180.0 2_676 . ?
C19 O1 Cu1 121.69(12) . . ?
C39 O3 Cu2 121.30(12) . . ?
C10 N1 Cu1 133.02(12) . . ?
C18 N1 Cu1 108.22(12) . . ?
C18 N1 C10 118.71(16) . . ?
C21 N2 Cu1 117.83(11) . . ?
C30 N3 Cu2 133.63(12) . . ?
C38 N3 Cu2 107.72(11) . . ?
C38 N3 C30 118.54(15) . . ?
C41 N4 Cu2 117.31(12) . . ?
N1 C10 C11 118.52(17) . . ?
N1 C10 C15 121.58(17) . . ?
C11 C10 C15 119.90(18) . . ?
C12 C11 C10 119.5(2) . . ?
C11 C12 C13 120.8(2) . . ?
C14 C13 C12 120.6(2) . . ?
C13 C14 C15 120.7(2) . . ?
C14 C15 C10 118.50(19) . . ?
C16 C15 C10 117.71(18) . . ?
C16 C15 C14 123.80(19) . . ?
C17 C16 C15 120.22(18) . . ?
C16 C17 C18 118.50(18) . . ?
N1 C18 C17 123.30(18) . . ?
N1 C18 C19 117.10(15) . . ?
C17 C18 C19 119.60(16) . . ?
O1 C19 C18 116.87(15) . . ?
O11 C19 O1 125.61(18) . . ?
O11 C19 C18 117.52(16) . . ?
N2 C21 C22 113.57(15) . . ?
C21 C22 C23 112.00(16) . . ?
O2 C23 C22 108.69(16) . . ?
N3 C30 C31 118.99(16) . . ?
N3 C30 C35 121.72(16) . . ?
C31 C30 C35 119.28(17) . . ?
C32 C31 C30 119.84(18) . . ?
C31 C32 C33 121.19(19) . . ?
C34 C33 C32 120.15(19) . . ?
C33 C34 C35 120.62(18) . . ?
C34 C35 C30 118.88(17) . . ?
C36 C35 C30 117.59(17) . . ?
C36 C35 C34 123.52(17) . . ?
C37 C36 C35 120.05(16) . . ?
C36 C37 C38 118.63(17) . . ?
N3 C38 C37 123.45(17) . . ?
N3 C38 C39 116.93(15) . . ?
C37 C38 C39 119.62(16) . . ?
O3 C39 C38 118.10(15) . . ?
O33 C39 O3 124.76(17) . . ?
O33 C39 C38 117.13(15) . . ?
N4 C41 C42 113.70(16) . . ?
C43 C42 C41 113.37(17) . . ?
O4 C43 C42 111.63(18) . . ?
N5 C51 C52 111.1(2) . . ?
C51 C52 C53 111.0(2) . . ?
O5 C53 C52 112.59(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
_geom_hbond_publ_flag
O2 H2 O33 0.73(3) 1.98(3) 2.684(2) 162(3) . yes
O4 H4 N5 0.81(2) 2.02(3) 2.820(3) 174(2) 2_666 yes
O5 H5 O2 0.880(10) 1.890(11) 2.764(3) 172(4) . yes
N2 H2A O11 0.88(2) 2.10(2) 2.968(2) 169(2) 1_455 yes
N2 H2B O4 0.85(2) 2.17(2) 2.981(2) 158(2) 2_666 yes
N4 H4A O33 0.87(2) 2.16(2) 3.023(2) 168(2) 1_655 yes
N4 H4B O5 0.87(3) 2.23(3) 3.037(2) 154(2) 1_655 yes

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.700
_oxdiff_exptl_absorpt_empirical_full_min 0.687
####################################################################### 
# 
# 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_anti11d2ACN
_database_code_depnum_ccdc_archive 'CCDC 2077013'
loop_
_audit_author_name
_audit_author_address
'Barbara Modec'
;University of Ljubljana
Slovenia
;
_audit_update_record             
;
2021-04-12 deposited with the CCDC.	2022-03-18 downloaded from the CCDC.
;
_audit_creation_date             2021-03-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H28 Cu2 N4 O6, 2(C2 H3 N)'
_chemical_formula_sum            'C30 H34 Cu2 N6 O6'
_chemical_formula_weight         701.71
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_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                   10.2380(3)
_cell_length_b                   12.0196(4)
_cell_length_c                   12.4708(4)
_cell_angle_alpha                90
_cell_angle_beta                 101.731(3)
_cell_angle_gamma                90
_cell_volume                     1502.56(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3224
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      74.8740
_cell_measurement_theta_min      5.0910
_shelx_estimated_absorpt_T_max   0.898
_shelx_estimated_absorpt_T_min   0.734
_exptl_absorpt_coefficient_mu    2.199
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.25764
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.551
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             724
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_unetI/netI     0.0294
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6232
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.082
_diffrn_reflns_theta_min         5.108
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -66.00  33.00   1.00    1.00    --  -41.63  37.00 120.00   99
  2  ω    -92.00 -66.00   1.00    1.00    --  -41.63 125.00-180.00   26
  3  ω   -108.00 -25.00   1.00    1.00    --  -41.63 -57.00 -30.00   83
  4  ω     87.00 134.00   1.00    3.50    --  109.50 -45.00-150.00   47
  5  ω    145.00 170.00   1.00    3.50    --  109.50  61.00  30.00   25
  6  ω     37.00 135.00   1.00    3.50    --  109.50 -45.00  30.00   98
  7  ω    118.00 178.00   1.00    3.50    --  109.50  61.00   0.00   60
  8  ω     40.00  66.00   1.00    3.50    --  109.50 -45.00-120.00   26
  9  ω     94.00 135.00   1.00    3.50    --  109.50 -45.00-120.00   41
 10  ω     81.00 114.00   1.00    3.50    --  109.50  61.00  30.00   33
 11  ω     47.00  74.00   1.00    3.50    --  109.50 -45.00-150.00   27
 12  ω     49.00  75.00   1.00    3.50    --  109.50-125.00   0.00   26
 13  ω     41.00 140.00   1.00    3.50    --  109.50 -77.00  30.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.1270023000
_diffrn_orient_matrix_UB_12      0.0178807000
_diffrn_orient_matrix_UB_13      0.0462117000
_diffrn_orient_matrix_UB_21      -0.0863118000
_diffrn_orient_matrix_UB_22      -0.0328530000
_diffrn_orient_matrix_UB_23      -0.1115609000
_diffrn_orient_matrix_UB_31      0.0047322000
_diffrn_orient_matrix_UB_32      -0.1226287000
_diffrn_orient_matrix_UB_33      0.0365732000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2753
_reflns_number_total             3028
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     70.93
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3028
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0312
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0522P)²+0.4004P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0823
_refine_ls_wR_factor_ref         0.0860
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17)
2.c Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.57238(2) 0.60790(2) 0.48584(2) 0.01637(10) Uani 1 1 d . . . . .
O1 O 0.77950(13) 0.60471(10) 0.58496(10) 0.0219(3) Uani 1 1 d . . . . .
O2 O 0.51481(14) 0.47046(11) 0.41152(10) 0.0249(3) Uani 1 1 d . . . . .
O11 O 0.91112(13) 0.70596(12) 0.71419(11) 0.0274(3) Uani 1 1 d . . . . .
N1 N 0.58265(14) 0.75572(12) 0.56869(11) 0.0168(3) Uani 1 1 d . . . . .
N2 N 0.62921(15) 0.67801(12) 0.35775(11) 0.0180(3) Uani 1 1 d . . . . .
H2A H 0.566(2) 0.718(2) 0.3278(19) 0.022(5) Uiso 1 1 d . . . . .
H2B H 0.694(3) 0.720(2) 0.385(2) 0.025(6) Uiso 1 1 d . . . . .
N3 N 0.9246(2) 0.7682(2) 0.4115(2) 0.0487(5) Uani 1 1 d . . . . .
C10 C 0.48007(16) 0.83082(14) 0.55784(13) 0.0173(3) Uani 1 1 d . . . . .
C11 C 0.36604(17) 0.81647(16) 0.47342(14) 0.0224(3) Uani 1 1 d . . . . .
H11 H 0.359451 0.754833 0.427560 0.027 Uiso 1 1 calc R . . . .
C12 C 0.26529(19) 0.89350(16) 0.45928(16) 0.0270(4) Uani 1 1 d . . . . .
H12 H 0.190962 0.883959 0.403204 0.032 Uiso 1 1 calc R . . . .
C13 C 0.27273(19) 0.98695(16) 0.52850(16) 0.0276(4) Uani 1 1 d . . . . .
H13 H 0.203919 1.038854 0.517401 0.033 Uiso 1 1 calc R . . . .
C14 C 0.38086(19) 1.00155(15) 0.61199(15) 0.0255(4) Uani 1 1 d . . . . .
H14 H 0.384634 1.062877 0.657994 0.031 Uiso 1 1 calc R . . . .
C15 C 0.48705(17) 0.92393(14) 0.62881(13) 0.0199(3) Uani 1 1 d . . . . .
C16 C 0.60217(19) 0.93573(15) 0.71218(14) 0.0239(4) Uani 1 1 d . . . . .
H16 H 0.608593 0.993965 0.762079 0.029 Uiso 1 1 calc R . . . .
C17 C 0.70427(18) 0.86088(15) 0.71908(13) 0.0217(3) Uani 1 1 d . . . . .
H17 H 0.781435 0.869024 0.772611 0.026 Uiso 1 1 calc R . . . .
C18 C 0.69189(17) 0.77152(14) 0.64476(12) 0.0180(3) Uani 1 1 d . . . . .
C19 C 0.80449(17) 0.68659(14) 0.64833(13) 0.0198(3) Uani 1 1 d . . . . .
C21 C 0.67010(19) 0.60200(15) 0.27714(15) 0.0241(4) Uani 1 1 d . . . . .
H21A H 0.748774 0.560779 0.312012 0.029 Uiso 1 1 calc R . . . .
H21B H 0.692616 0.645030 0.217632 0.029 Uiso 1 1 calc R . . . .
C22 C 0.55852(18) 0.52137(15) 0.23191(13) 0.0224(3) Uani 1 1 d . . . . .
H22A H 0.576786 0.487638 0.165847 0.027 Uiso 1 1 calc R . . . .
H22B H 0.475710 0.562620 0.211821 0.027 Uiso 1 1 calc R . . . .
C23 C 0.54025(19) 0.42963(15) 0.31157(14) 0.0232(3) Uani 1 1 d . . . . .
H23A H 0.466606 0.382461 0.277389 0.028 Uiso 1 1 calc R . . . .
H23B H 0.620132 0.384118 0.326631 0.028 Uiso 1 1 calc R . . . .
C31 C 0.9995(2) 0.7085(2) 0.46137(19) 0.0359(5) Uani 1 1 d . . . . .
C32 C 1.0947(2) 0.6335(2) 0.5272(2) 0.0407(5) Uani 1 1 d . . . . .
H32A H 1.109244 0.570531 0.483784 0.061 Uiso 1 1 calc GR . . . .
H32B H 1.060293 0.608739 0.589183 0.061 Uiso 1 1 calc GR . . . .
H32C H 1.177642 0.671848 0.552157 0.061 Uiso 1 1 calc GR . . . .


_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 Cu1 3.0433(5) 3_666 ?
Cu1 O1 2.2271(13) . ?
Cu1 O2 1.9459(12) 3_666 ?
Cu1 O2 1.9270(12) . ?
Cu1 N1 2.0472(14) . ?
Cu1 N2 1.9946(14) . ?
O1 C19 1.256(2) . ?
O2 C23 1.412(2) . ?
O11 C19 1.247(2) . ?
N1 C10 1.371(2) . ?
N1 C18 1.325(2) . ?
N2 C21 1.481(2) . ?
N3 C31 1.139(3) . ?
C10 C11 1.415(2) . ?
C10 C15 1.419(2) . ?
C11 C12 1.370(3) . ?
C12 C13 1.409(3) . ?
C13 C14 1.368(3) . ?
C14 C15 1.415(3) . ?
C15 C16 1.411(3) . ?
C16 C17 1.368(3) . ?
C17 C18 1.408(2) . ?
C18 C19 1.534(2) . ?
C21 C22 1.517(2) . ?
C22 C23 1.521(2) . ?
C31 C32 1.453(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 Cu1 110.62(3) . 3_666 ?
O2 Cu1 Cu1 37.99(4) 3_666 3_666 ?
O2 Cu1 Cu1 38.43(3) . 3_666 ?
O2 Cu1 O1 114.57(6) . . ?
O2 Cu1 O1 97.99(5) 3_666 . ?
O2 Cu1 O2 76.42(5) . 3_666 ?
O2 Cu1 N1 165.03(6) . . ?
O2 Cu1 N1 94.10(5) 3_666 . ?
O2 Cu1 N2 168.18(6) 3_666 . ?
O2 Cu1 N2 95.02(5) . . ?
N1 Cu1 Cu1 131.10(4) . 3_666 ?
N1 Cu1 O1 77.84(5) . . ?
N2 Cu1 Cu1 132.94(4) . 3_666 ?
N2 Cu1 O1 92.97(5) . . ?
N2 Cu1 N1 92.53(6) . . ?
C19 O1 Cu1 112.65(11) . . ?
Cu1 O2 Cu1 103.58(5) . 3_666 ?
C23 O2 Cu1 128.99(11) . . ?
C23 O2 Cu1 127.16(11) . 3_666 ?
C10 N1 Cu1 124.20(11) . . ?
C18 N1 Cu1 115.79(12) . . ?
C18 N1 C10 119.64(14) . . ?
C21 N2 Cu1 116.86(11) . . ?
N1 C10 C11 119.54(15) . . ?
N1 C10 C15 121.15(15) . . ?
C11 C10 C15 119.30(16) . . ?
C12 C11 C10 119.94(17) . . ?
C11 C12 C13 120.94(18) . . ?
C14 C13 C12 120.19(17) . . ?
C13 C14 C15 120.43(17) . . ?
C14 C15 C10 119.18(16) . . ?
C16 C15 C10 117.85(16) . . ?
C16 C15 C14 122.96(17) . . ?
C17 C16 C15 119.54(16) . . ?
C16 C17 C18 119.66(16) . . ?
N1 C18 C17 122.06(16) . . ?
N1 C18 C19 116.45(14) . . ?
C17 C18 C19 121.49(15) . . ?
O1 C19 C18 116.60(14) . . ?
O11 C19 O1 126.85(17) . . ?
O11 C19 C18 116.55(15) . . ?
N2 C21 C22 110.56(14) . . ?
C21 C22 C23 113.81(15) . . ?
O2 C23 C22 113.19(14) . . ?
N3 C31 C32 178.7(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2A O11 0.83(3) 2.11(3) 2.9172(19) 165(2) 4_575 yes

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.292
_oxdiff_exptl_absorpt_empirical_full_min 0.586
####################################################################### 
# 
# 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_8c
_database_code_depnum_ccdc_archive 'CCDC 2077002'
loop_
_audit_author_name
_audit_author_address
'Barbara Modec'
;University of Ljubljana
Slovenia
;
_audit_update_record             
;
2021-04-12 deposited with the CCDC.	2022-03-18 downloaded from the CCDC.
;
_audit_creation_date             2021-03-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C23 H21 Cu N3 O5'
_chemical_formula_sum            'C23 H21 Cu N3 O5'
_chemical_formula_weight         482.97
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_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                   10.2710(6)
_cell_length_b                   7.6001(4)
_cell_length_c                   13.5989(8)
_cell_angle_alpha                90
_cell_angle_beta                 108.617(6)
_cell_angle_gamma                90
_cell_volume                     1005.99(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2434
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      29.7700
_cell_measurement_theta_min      2.9970
_shelx_estimated_absorpt_T_max   0.946
_shelx_estimated_absorpt_T_min   0.766
_exptl_absorpt_coefficient_mu    1.129
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.58640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.594
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             498
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_unetI/netI     0.0490
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.871
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5118
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.871
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.248
_diffrn_reflns_theta_min         2.998
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.871
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     19.00  80.00   1.00   10.00    --   14.05  37.00  60.00   61
  2  ω    -51.00  59.00   1.00   10.00    --   14.05 -19.00-120.00  110
  3  ω    -84.00 -59.00   1.00   10.00    --  -14.36 178.00   0.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0426281000
_diffrn_orient_matrix_UB_12      0.0007244000
_diffrn_orient_matrix_UB_13      0.0319823000
_diffrn_orient_matrix_UB_21      -0.0452710000
_diffrn_orient_matrix_UB_22      0.0597124000
_diffrn_orient_matrix_UB_23      -0.0346002000
_diffrn_orient_matrix_UB_31      -0.0380157000
_diffrn_orient_matrix_UB_32      -0.0717430000
_diffrn_orient_matrix_UB_33      -0.0284506000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2091
_reflns_number_total             2606
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.514
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     170
_refine_ls_number_reflns         2606
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0498
_refine_ls_R_factor_gt           0.0359
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0338P)²+0.5354P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0810
_refine_ls_wR_factor_ref         0.0910
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Fixed Sof: O2(0.5) H2(0.5) N2(0.5) H2A(0.5) H2B(0.5) C21(0.5) H21(0.5)
 C22(0.5) H22A(0.5) H22B(0.5) C23(0.5) H23A(0.5) H23B(0.5) H23C(0.5)
3.a Ternary CH refined with riding coordinates:
 C21(H21)
3.b Secondary CH2 refined with riding coordinates:
 N2(H2A,H2B), C22(H22A,H22B)
3.c Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17)
3.d Tetrahedral OH refined with riding coordinates:
 O2(H2)
3.e Idealised Me refined as rotating group:
 C23(H23A,H23B,H23C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.500000 0.500000 0.500000 0.01260(11) Uani 1 2 d S T P . .
O1 O 0.43977(14) 0.5519(2) 0.35155(11) 0.0189(3) Uani 1 1 d . . . . .
O11 O 0.27460(17) 0.6521(3) 0.21395(12) 0.0328(4) Uani 1 1 d . . . . .
N1 N 0.2802(2) 0.5794(3) 0.47093(14) 0.0258(4) Uani 1 1 d . . . . .
C10 C 0.2056(2) 0.6070(3) 0.53779(18) 0.0259(5) Uani 1 1 d . . . . .
C11 C 0.2551(3) 0.5363(3) 0.63899(19) 0.0286(5) Uani 1 1 d . . . . .
H11 H 0.335796 0.470856 0.659333 0.034 Uiso 1 1 calc R . . . .
C12 C 0.1835(3) 0.5647(4) 0.70713(19) 0.0321(6) Uani 1 1 d . . . . .
H12 H 0.215449 0.516486 0.773371 0.039 Uiso 1 1 calc R . . . .
C13 C 0.0624(2) 0.6658(4) 0.6784(2) 0.0328(6) Uani 1 1 d . . . . .
H13 H 0.016033 0.685301 0.726010 0.039 Uiso 1 1 calc R . . . .
C14 C 0.0126(3) 0.7352(3) 0.5813(2) 0.0309(6) Uani 1 1 d . . . . .
H14 H -0.067824 0.801248 0.562913 0.037 Uiso 1 1 calc R . . . .
C15 C 0.0829(2) 0.7072(3) 0.50779(19) 0.0272(5) Uani 1 1 d . . . . .
C16 C 0.0370(3) 0.7753(3) 0.4062(2) 0.0313(6) Uani 1 1 d . . . . .
H16 H -0.043033 0.841942 0.384300 0.038 Uiso 1 1 calc R . . . .
C17 C 0.1096(2) 0.7436(3) 0.34030(19) 0.0289(5) Uani 1 1 d . . . . .
H17 H 0.079253 0.786662 0.272781 0.035 Uiso 1 1 calc R . . . .
C18 C 0.2313(2) 0.6445(3) 0.37574(17) 0.0222(5) Uani 1 1 d . . . . .
C19 C 0.3200(2) 0.6140(3) 0.30691(16) 0.0208(5) Uani 1 1 d . . . . .
O2 O 0.5739(4) -0.2159(5) 0.5350(3) 0.0265(9) Uani 0.5 1 d . . . A -1
H2 H 0.601850 -0.186249 0.596200 0.040 Uiso 0.5 1 calc R . . A -1
N2 N 0.4784(4) 0.2440(6) 0.4483(3) 0.0170(9) Uani 0.5 1 d . . . A -1
H2A H 0.392686 0.233188 0.405706 0.020 Uiso 0.5 1 calc R . . A -1
H2B H 0.533153 0.231202 0.409577 0.020 Uiso 0.5 1 calc R . . A -1
C21 C 0.5037(6) 0.0937(8) 0.5183(5) 0.0218(12) Uani 0.5 1 d . . . A -1
H21 H 0.575855 0.124953 0.582825 0.026 Uiso 0.5 1 calc R . . A -1
C22 C 0.5496(7) -0.0652(8) 0.4717(4) 0.0224(12) Uani 0.5 1 d . . . A -1
H22A H 0.479895 -0.092742 0.406338 0.027 Uiso 0.5 1 calc R . . A -1
H22B H 0.633296 -0.035779 0.456829 0.027 Uiso 0.5 1 calc R . . A -1
C23 C 0.3695(6) 0.0544(8) 0.5431(4) 0.0319(11) Uani 0.5 1 d . . . A -1
H23A H 0.342102 0.157226 0.572506 0.048 Uiso 0.5 1 calc GR . . A -1
H23B H 0.384996 -0.040946 0.591820 0.048 Uiso 0.5 1 calc GR . . A -1
H23C H 0.298357 0.022532 0.480458 0.048 Uiso 0.5 1 calc GR . . A -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_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.9535(14) . ?
Cu1 O1 1.9536(14) 3_666 ?
Cu1 N1 2.2466(19) 3_666 ?
Cu1 N1 2.2466(19) . ?
Cu1 N2 2.056(5) . ?
O1 C19 1.276(3) . ?
O11 C19 1.234(3) . ?
N1 C10 1.380(3) . ?
N1 C18 1.326(3) . ?
C10 C11 1.412(3) . ?
C10 C15 1.416(3) . ?
C11 C12 1.372(3) . ?
C12 C13 1.407(4) . ?
C13 C14 1.360(4) . ?
C14 C15 1.424(3) . ?
C15 C16 1.407(3) . ?
C16 C17 1.358(3) . ?
C17 C18 1.406(3) . ?
C18 C19 1.518(3) . ?
O2 C22 1.407(8) . ?
N2 C21 1.456(8) . ?
C21 C22 1.507(7) . ?
C21 C23 1.550(7) . ?

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 Cu1 O1 180.00(9) . 3_666 ?
O1 Cu1 N1 101.83(6) . 3_666 ?
O1 Cu1 N1 78.17(6) 3_666 3_666 ?
O1 Cu1 N1 78.17(6) . . ?
O1 Cu1 N1 101.83(6) 3_666 . ?
O1 Cu1 N2 82.75(13) . . ?
O1 Cu1 N2 97.25(13) 3_666 . ?
N1 Cu1 N1 180.0 . 3_666 ?
N2 Cu1 N1 101.61(13) . . ?
N2 Cu1 N1 78.39(13) . 3_666 ?
C19 O1 Cu1 120.36(13) . . ?
C10 N1 Cu1 131.56(16) . . ?
C18 N1 Cu1 108.55(14) . . ?
C18 N1 C10 118.02(19) . . ?
N1 C10 C11 118.8(2) . . ?
N1 C10 C15 121.5(2) . . ?
C11 C10 C15 119.7(2) . . ?
C12 C11 C10 119.6(2) . . ?
C11 C12 C13 121.0(2) . . ?
C14 C13 C12 120.4(2) . . ?
C13 C14 C15 120.4(2) . . ?
C10 C15 C14 118.8(2) . . ?
C16 C15 C10 118.0(2) . . ?
C16 C15 C14 123.2(2) . . ?
C17 C16 C15 120.0(2) . . ?
C16 C17 C18 119.0(2) . . ?
N1 C18 C17 123.6(2) . . ?
N1 C18 C19 115.48(19) . . ?
C17 C18 C19 120.89(19) . . ?
O1 C19 C18 116.14(18) . . ?
O11 C19 O1 124.4(2) . . ?
O11 C19 C18 119.41(19) . . ?
C21 N2 Cu1 122.8(3) . . ?
N2 C21 C22 111.6(5) . . ?
N2 C21 C23 108.0(5) . . ?
C22 C21 C23 110.9(6) . . ?
O2 C22 C21 114.4(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
_geom_hbond_publ_flag
O2 H2 O11 0.82 1.99 2.684(4) 141.7 4_666 yes
N2 H2A O11 0.89 2.05 2.907(5) 161.8 2_545 yes

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.643
_oxdiff_exptl_absorpt_empirical_full_min 0.584
####################################################################### 
# 
# 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_syn11d2H2O
_database_code_depnum_ccdc_archive 'CCDC 2077012'
loop_
_audit_author_name
_audit_author_address
'Barbara Modec'
;University of Ljubljana
Slovenia
;
_audit_update_record             
;
2021-04-12 deposited with the CCDC.	2022-03-18 downloaded from the CCDC.
;
_audit_creation_date             2021-03-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H28 Cu2 N4 O6, 2(H2 O)'
_chemical_formula_sum            'C26 H32 Cu2 N4 O8'
_chemical_formula_weight         655.63
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.0507(4)
_cell_length_b                   11.5520(5)
_cell_length_c                   12.1515(6)
_cell_angle_alpha                82.366(4)
_cell_angle_beta                 83.857(4)
_cell_angle_gamma                81.000(4)
_cell_volume                     1375.77(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5093
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      29.3720
_cell_measurement_theta_min      3.9980
_shelx_estimated_absorpt_T_max   0.856
_shelx_estimated_absorpt_T_min   0.690
_exptl_absorpt_coefficient_mu    1.602
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88122
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.583
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.851
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13264
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.851
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.081
_diffrn_reflns_theta_min         2.820
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector_area_resol_mean 10.4933
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.851
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -19.00   28.00   1.0000    9.6000
omega____ theta____ kappa____ phi______ frames
    -      -13.2035  -99.0000 -120.0000 47

#__ type_ start__ end____ width___ exp.time_
  2 omega -102.00  -77.00   1.0000    9.6000
omega____ theta____ kappa____ phi______ frames
    -      -13.2035  178.0000  -90.0000 25

#__ type_ start__ end____ width___ exp.time_
  3 omega  -96.00  -57.00   1.0000    9.6000
omega____ theta____ kappa____ phi______ frames
    -      -13.2035 -178.0000  120.0000 39

#__ type_ start__ end____ width___ exp.time_
  4 omega  -12.00   75.00   1.0000    9.6000
omega____ theta____ kappa____ phi______ frames
    -       13.3597   37.0000 -180.0000 87

#__ type_ start__ end____ width___ exp.time_
  5 omega   -9.00   30.00   1.0000    9.6000
omega____ theta____ kappa____ phi______ frames
    -       13.3597  -37.0000 -120.0000 39

#__ type_ start__ end____ width___ exp.time_
  6 omega  -29.00   94.00   1.0000    9.6000
omega____ theta____ kappa____ phi______ frames
    -       13.3597   19.0000   90.0000 123
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0182139000
_diffrn_orient_matrix_UB_12      -0.0318265000
_diffrn_orient_matrix_UB_13      -0.0467172000
_diffrn_orient_matrix_UB_21      0.0514577000
_diffrn_orient_matrix_UB_22      0.0354240000
_diffrn_orient_matrix_UB_23      -0.0187608000
_diffrn_orient_matrix_UB_31      0.0465371000
_diffrn_orient_matrix_UB_32      -0.0406402000
_diffrn_orient_matrix_UB_33      0.0310013000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5679
_reflns_number_total             6877
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.01
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.077
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     393
_refine_ls_number_reflns         6877
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0486
_refine_ls_R_factor_gt           0.0368
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0281P)²+1.3195P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0840
_refine_ls_wR_factor_ref         0.0909
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C31(H31A,H31B), C32(H32A,H32B), C33(H33A,H33B), C41(H41A,H41B), C42(H42A,
 H42B), C43(H43A,H43B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17), C21(H21),
 C22(H22), C23(H23), C24(H24), C26(H26), C27(H27)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.65466(3) 0.68307(2) 0.83734(2) 0.01939(8) Uani 1 1 d . . . . .
Cu2 Cu 0.34764(3) 0.71265(2) 0.84563(2) 0.01925(8) Uani 1 1 d . . . . .
O1 O 0.78523(18) 0.78607(15) 0.86974(15) 0.0254(4) Uani 1 1 d . . . . .
O2 O 0.22247(17) 0.59238(15) 0.88974(14) 0.0239(4) Uani 1 1 d . . . . .
O3 O 0.50729(17) 0.59519(14) 0.82965(15) 0.0233(4) Uani 1 1 d . . . . .
O4 O 0.49552(17) 0.80191(14) 0.83982(15) 0.0241(4) Uani 1 1 d . . . . .
O5 O 0.1086(3) 0.24377(19) 0.9177(2) 0.0385(5) Uani 1 1 d . . . . .
H5A H 0.103(3) 0.309(3) 0.900(3) 0.034(9) Uiso 1 1 d . . . . .
H5B H 0.130(4) 0.233(3) 0.978(3) 0.046(11) Uiso 1 1 d . . . . .
O6 O -0.1028(3) 0.1398(2) 0.8586(2) 0.0399(5) Uani 1 1 d . . . . .
H6A H -0.086(4) 0.076(3) 0.852(3) 0.039(10) Uiso 1 1 d . . . . .
H6B H -0.036(4) 0.164(3) 0.861(3) 0.057(13) Uiso 1 1 d . . . . .
O11 O 0.94280(19) 0.89990(15) 0.80414(17) 0.0309(4) Uani 1 1 d . . . . .
O22 O 0.08035(18) 0.48474(15) 0.83740(16) 0.0273(4) Uani 1 1 d . . . . .
N1 N 0.7504(2) 0.74698(17) 0.66285(17) 0.0195(4) Uani 1 1 d . . . . .
N2 N 0.2554(2) 0.70164(17) 0.68123(16) 0.0202(4) Uani 1 1 d . . . . .
N3 N 0.7842(2) 0.54024(19) 0.8793(2) 0.0232(4) Uani 1 1 d . . . . .
H3A H 0.773(3) 0.524(2) 0.950(3) 0.026(8) Uiso 1 1 d . . . . .
H3B H 0.864(3) 0.553(3) 0.859(3) 0.032(8) Uiso 1 1 d . . . . .
N4 N 0.2077(2) 0.8373(2) 0.9008(2) 0.0268(5) Uani 1 1 d . . . . .
H4A H 0.198(3) 0.821(2) 0.972(3) 0.026(8) Uiso 1 1 d . . . . .
H4B H 0.138(3) 0.832(3) 0.875(3) 0.036(9) Uiso 1 1 d . . . . .
C10 C 0.7265(2) 0.7292(2) 0.5578(2) 0.0205(5) Uani 1 1 d . . . . .
C11 C 0.6309(3) 0.6556(2) 0.5458(2) 0.0276(6) Uani 1 1 d . . . . .
H11 H 0.585821 0.619390 0.608755 0.033 Uiso 1 1 calc R . . . .
C12 C 0.6041(3) 0.6375(3) 0.4422(2) 0.0350(7) Uani 1 1 d . . . . .
H12 H 0.540323 0.589344 0.434916 0.042 Uiso 1 1 calc R . . . .
C13 C 0.6725(3) 0.6913(2) 0.3461(2) 0.0325(6) Uani 1 1 d . . . . .
H13 H 0.653413 0.678215 0.275919 0.039 Uiso 1 1 calc R . . . .
C14 C 0.7658(3) 0.7619(2) 0.3548(2) 0.0311(6) Uani 1 1 d . . . . .
H14 H 0.810787 0.796220 0.290847 0.037 Uiso 1 1 calc R . . . .
C15 C 0.7949(3) 0.7836(2) 0.4614(2) 0.0243(5) Uani 1 1 d . . . . .
C16 C 0.8891(3) 0.8573(2) 0.4769(2) 0.0329(6) Uani 1 1 d . . . . .
H16 H 0.935864 0.894488 0.415421 0.040 Uiso 1 1 calc R . . . .
C17 C 0.9115(3) 0.8741(2) 0.5813(2) 0.0314(6) Uani 1 1 d . . . . .
H17 H 0.973853 0.922107 0.592198 0.038 Uiso 1 1 calc R . . . .
C18 C 0.8385(2) 0.8173(2) 0.6733(2) 0.0214(5) Uani 1 1 d . . . . .
C19 C 0.8582(2) 0.8365(2) 0.7913(2) 0.0225(5) Uani 1 1 d . . . . .
C20 C 0.2757(2) 0.7566(2) 0.5752(2) 0.0219(5) Uani 1 1 d . . . . .
C21 C 0.3536(3) 0.8496(2) 0.5558(2) 0.0317(6) Uani 1 1 d . . . . .
H21 H 0.391720 0.872252 0.614606 0.038 Uiso 1 1 calc R . . . .
C22 C 0.3734(3) 0.9066(3) 0.4511(2) 0.0381(7) Uani 1 1 d . . . . .
H22 H 0.424458 0.968331 0.439062 0.046 Uiso 1 1 calc R . . . .
C23 C 0.3174(3) 0.8731(3) 0.3608(2) 0.0360(7) Uani 1 1 d . . . . .
H23 H 0.332195 0.912646 0.289741 0.043 Uiso 1 1 calc R . . . .
C24 C 0.2421(3) 0.7837(2) 0.3767(2) 0.0325(6) Uani 1 1 d . . . . .
H24 H 0.205552 0.762476 0.316410 0.039 Uiso 1 1 calc R . . . .
C25 C 0.2186(3) 0.7224(2) 0.4842(2) 0.0260(5) Uani 1 1 d . . . . .
C26 C 0.1381(3) 0.6311(2) 0.5081(2) 0.0320(6) Uani 1 1 d . . . . .
H26 H 0.099441 0.606150 0.450821 0.038 Uiso 1 1 calc R . . . .
C27 C 0.1165(3) 0.5794(2) 0.6141(2) 0.0285(6) Uani 1 1 d . . . . .
H27 H 0.062328 0.519993 0.630354 0.034 Uiso 1 1 calc R . . . .
C28 C 0.1779(2) 0.6177(2) 0.6989(2) 0.0205(5) Uani 1 1 d . . . . .
C29 C 0.1570(2) 0.5600(2) 0.8182(2) 0.0200(5) Uani 1 1 d . . . . .
C31 C 0.7662(3) 0.4318(2) 0.8330(3) 0.0298(6) Uani 1 1 d . . . . .
H31A H 0.835643 0.367935 0.856852 0.036 Uiso 1 1 calc R . . . .
H31B H 0.776285 0.445311 0.752242 0.036 Uiso 1 1 calc R . . . .
C32 C 0.6281(3) 0.3968(2) 0.8714(2) 0.0256(5) Uani 1 1 d . . . . .
H32A H 0.628194 0.316213 0.856942 0.031 Uiso 1 1 calc R . . . .
H32B H 0.611880 0.398711 0.951343 0.031 Uiso 1 1 calc R . . . .
C33 C 0.5133(3) 0.4751(2) 0.8156(2) 0.0241(5) Uani 1 1 d . . . . .
H33A H 0.524085 0.466985 0.736605 0.029 Uiso 1 1 calc R . . . .
H33B H 0.428520 0.448683 0.846240 0.029 Uiso 1 1 calc R . . . .
C41 C 0.2328(3) 0.9609(2) 0.8762(3) 0.0438(8) Uani 1 1 d . . . . .
H41A H 0.161366 1.011233 0.914580 0.053 Uiso 1 1 calc R . . . .
H41B H 0.230923 0.985272 0.796777 0.053 Uiso 1 1 calc R . . . .
C42 C 0.3688(3) 0.9765(2) 0.9124(3) 0.0383(7) Uani 1 1 d . . . . .
H42A H 0.372055 1.059980 0.912031 0.046 Uiso 1 1 calc R . . . .
H42B H 0.376681 0.939027 0.988178 0.046 Uiso 1 1 calc R . . . .
C43 C 0.4880(3) 0.9245(2) 0.8380(2) 0.0280(6) Uani 1 1 d . . . . .
H43A H 0.480284 0.961733 0.762115 0.034 Uiso 1 1 calc R . . . .
H43B H 0.570902 0.941791 0.862199 0.034 Uiso 1 1 calc R . . . .


_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 Cu2 3.0433(4) . ?
Cu1 O1 2.0041(17) . ?
Cu1 O3 1.9387(16) . ?
Cu1 O4 1.9384(17) . ?
Cu1 N1 2.310(2) . ?
Cu1 N3 1.981(2) . ?
Cu2 O2 2.0012(17) . ?
Cu2 O3 1.9432(17) . ?
Cu2 O4 1.9275(16) . ?
Cu2 N2 2.3170(19) . ?
Cu2 N4 1.980(2) . ?
O1 C19 1.273(3) . ?
O2 C29 1.271(3) . ?
O3 C33 1.412(3) . ?
O4 C43 1.404(3) . ?
O11 C19 1.240(3) . ?
O22 C29 1.233(3) . ?
N1 C10 1.371(3) . ?
N1 C18 1.317(3) . ?
N2 C20 1.368(3) . ?
N2 C28 1.318(3) . ?
N3 C31 1.482(3) . ?
N4 C41 1.475(4) . ?
C10 C11 1.409(3) . ?
C10 C15 1.417(3) . ?
C11 C12 1.364(4) . ?
C12 C13 1.412(4) . ?
C13 C14 1.356(4) . ?
C14 C15 1.420(4) . ?
C15 C16 1.411(4) . ?
C16 C17 1.355(4) . ?
C17 C18 1.414(4) . ?
C18 C19 1.519(4) . ?
C20 C21 1.407(4) . ?
C20 C25 1.425(3) . ?
C21 C22 1.363(4) . ?
C22 C23 1.408(4) . ?
C23 C24 1.355(4) . ?
C24 C25 1.416(4) . ?
C25 C26 1.410(4) . ?
C26 C27 1.355(4) . ?
C27 C28 1.408(3) . ?
C28 C29 1.521(3) . ?
C31 C32 1.515(4) . ?
C32 C33 1.512(3) . ?
C41 C42 1.523(4) . ?
C42 C43 1.516(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 Cu2 133.39(5) . . ?
O1 Cu1 N1 76.46(7) . . ?
O3 Cu1 Cu2 38.43(5) . . ?
O3 Cu1 O1 169.16(8) . . ?
O3 Cu1 N1 112.28(7) . . ?
O3 Cu1 N3 93.99(8) . . ?
O4 Cu1 Cu2 37.95(5) . . ?
O4 Cu1 O1 96.74(7) . . ?
O4 Cu1 O3 76.17(7) . . ?
O4 Cu1 N1 97.51(7) . . ?
O4 Cu1 N3 161.27(9) . . ?
N1 Cu1 Cu2 111.81(5) . . ?
N3 Cu1 Cu2 129.28(7) . . ?
N3 Cu1 O1 90.43(8) . . ?
N3 Cu1 N1 100.99(9) . . ?
O2 Cu2 Cu1 129.57(5) . . ?
O2 Cu2 N2 76.60(7) . . ?
O3 Cu2 Cu1 38.32(5) . . ?
O3 Cu2 O2 93.86(7) . . ?
O3 Cu2 N2 99.24(7) . . ?
O3 Cu2 N4 163.74(9) . . ?
O4 Cu2 Cu1 38.20(5) . . ?
O4 Cu2 O2 162.82(7) . . ?
O4 Cu2 O3 76.32(7) . . ?
O4 Cu2 N2 118.50(7) . . ?
O4 Cu2 N4 95.25(9) . . ?
N2 Cu2 Cu1 116.86(5) . . ?
N4 Cu2 Cu1 130.85(7) . . ?
N4 Cu2 O2 90.61(9) . . ?
N4 Cu2 N2 97.01(9) . . ?
C19 O1 Cu1 120.97(16) . . ?
C29 O2 Cu2 121.05(15) . . ?
Cu1 O3 Cu2 103.25(8) . . ?
C33 O3 Cu1 128.76(15) . . ?
C33 O3 Cu2 127.98(15) . . ?
Cu2 O4 Cu1 103.85(8) . . ?
C43 O4 Cu1 128.65(15) . . ?
C43 O4 Cu2 127.50(15) . . ?
C10 N1 Cu1 132.01(15) . . ?
C18 N1 Cu1 109.24(16) . . ?
C18 N1 C10 118.7(2) . . ?
C20 N2 Cu2 132.58(16) . . ?
C28 N2 Cu2 108.56(15) . . ?
C28 N2 C20 118.6(2) . . ?
C31 N3 Cu1 115.98(16) . . ?
C41 N4 Cu2 118.1(2) . . ?
N1 C10 C11 119.0(2) . . ?
N1 C10 C15 121.6(2) . . ?
C11 C10 C15 119.4(2) . . ?
C12 C11 C10 120.2(3) . . ?
C11 C12 C13 120.4(3) . . ?
C14 C13 C12 120.8(3) . . ?
C13 C14 C15 120.2(3) . . ?
C10 C15 C14 119.0(2) . . ?
C16 C15 C10 117.7(2) . . ?
C16 C15 C14 123.3(2) . . ?
C17 C16 C15 120.0(2) . . ?
C16 C17 C18 118.9(2) . . ?
N1 C18 C17 123.2(2) . . ?
N1 C18 C19 116.4(2) . . ?
C17 C18 C19 120.4(2) . . ?
O1 C19 C18 116.9(2) . . ?
O11 C19 O1 125.1(2) . . ?
O11 C19 C18 118.0(2) . . ?
N2 C20 C21 119.3(2) . . ?
N2 C20 C25 121.4(2) . . ?
C21 C20 C25 119.3(2) . . ?
C22 C21 C20 120.1(3) . . ?
C21 C22 C23 120.8(3) . . ?
C24 C23 C22 120.5(3) . . ?
C23 C24 C25 120.6(2) . . ?
C24 C25 C20 118.6(2) . . ?
C26 C25 C20 117.3(2) . . ?
C26 C25 C24 124.0(2) . . ?
C27 C26 C25 120.5(2) . . ?
C26 C27 C28 118.5(2) . . ?
N2 C28 C27 123.6(2) . . ?
N2 C28 C29 116.8(2) . . ?
C27 C28 C29 119.6(2) . . ?
O2 C29 C28 116.7(2) . . ?
O22 C29 O2 125.4(2) . . ?
O22 C29 C28 117.9(2) . . ?
N3 C31 C32 111.0(2) . . ?
C33 C32 C31 114.0(2) . . ?
O3 C33 C32 112.85(19) . . ?
N4 C41 C42 111.6(2) . . ?
C43 C42 C41 113.1(3) . . ?
O4 C43 C42 112.4(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
_geom_hbond_publ_flag
O5 H5A O22 0.75(3) 2.06(3) 2.806(3) 175(3) . yes
O5 H5B O1 0.77(4) 2.09(4) 2.858(3) 171(4) 2_667 yes
O6 H6A O11 0.74(4) 2.16(4) 2.890(3) 169(4) 1_445 yes
O6 H6B O5 0.77(4) 2.06(4) 2.797(3) 160(4) . yes
N3 H3A O2 0.85(3) 2.21(3) 3.013(3) 156(3) 2_667 yes
N3 H3B O22 0.84(3) 2.20(3) 2.949(3) 148(3) 1_655 yes
N4 H4A O6 0.86(3) 2.24(3) 3.031(4) 152(3) 2_567 yes
N4 H4B O11 0.81(3) 2.22(3) 2.973(3) 156(3) 1_455 yes

####################################################################### 
# 
# 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_7e
_database_code_depnum_ccdc_archive 'CCDC 2077000'
loop_
_audit_author_name
_audit_author_address
'Barbara Modec'
;University of Ljubljana
Slovenia
;
_audit_update_record             
;
2021-04-12 deposited with the CCDC.	2022-03-18 downloaded from the CCDC.
;
_audit_creation_date             2021-03-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H33 Cu N3 O3, 2(C10 H6 N O2)'
_chemical_formula_sum            'C32 H45 Cu N5 O7'
_chemical_formula_weight         675.27
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.3901(5)
_cell_length_b                   12.8020(6)
_cell_length_c                   13.0487(6)
_cell_angle_alpha                66.301(4)
_cell_angle_beta                 70.763(4)
_cell_angle_gamma                87.575(4)
_cell_volume                     1636.01(14)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4955
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      29.3980
_cell_measurement_theta_min      2.9890
_shelx_estimated_absorpt_T_max   0.965
_shelx_estimated_absorpt_T_min   0.761
_exptl_absorpt_coefficient_mu    0.721
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.40525
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.68a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             714
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0341
_diffrn_reflns_av_unetI/netI     0.0668
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.873
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16213
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.873
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.182
_diffrn_reflns_theta_min         2.446
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.873
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -16.00  88.00   1.00   80.00    --   14.05  57.00 -30.00  104
  2  ω    -41.00 -12.00   1.00   80.00    --   14.05 -77.00-180.00   29
  3  ω     -2.00  46.00   1.00   80.00    --   14.05 -77.00-180.00   48
  4  ω     -2.00  27.00   1.00   80.00    --   14.05 -99.00-180.00   29
  5  ω    -42.00  58.00   1.00   80.00    --  -14.36  57.00  60.00  100
  6  ω    -37.00  18.00   1.00   80.00    --  -14.36 -77.00  30.00   55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0576618000
_diffrn_orient_matrix_UB_12      0.0266591000
_diffrn_orient_matrix_UB_13      -0.0081198000
_diffrn_orient_matrix_UB_21      -0.0018625000
_diffrn_orient_matrix_UB_22      -0.0407561000
_diffrn_orient_matrix_UB_23      0.0569012000
_diffrn_orient_matrix_UB_31      0.0327046000
_diffrn_orient_matrix_UB_32      -0.0364649000
_diffrn_orient_matrix_UB_33      -0.0261888000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6150
_reflns_number_total             8449
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.68a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.792
_refine_diff_density_min         -0.445
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     477
_refine_ls_number_reflns         8449
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0791
_refine_ls_R_factor_gt           0.0490
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0420P)²+0.4933P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1109
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C24A) = Uanis(C24)
3. Others
 Sof(C21A)=Sof(H21C)=Sof(H21D)=Sof(C22A)=Sof(H22A)=Sof(C23A)=Sof(H23C)=
 Sof(H23D)=Sof(C24A)=Sof(H24D)=Sof(H24E)=Sof(H24F)=1-FVAR(1)
 Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(C22)=Sof(H22)=Sof(C23)=Sof(H23A)=Sof(H23B)=
 Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(H24C)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C12(H12), C32(H32), C22(H22), C22A(H22A)
4.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C13(H13A,H13B), C31(H31A,H31B), C33(H33A,H33B), C21(H21A,
 H21B), C23(H23A,H23B), C21A(H21C,H21D), C23A(H23C,H23D)
4.c Aromatic/amide H refined with riding coordinates:
 C41(H41), C42(H42), C43(H43), C44(H44), C46(H46), C47(H47), C51(H51),
 C52(H52), C53(H53), C54(H54), C56(H56), C57(H57)
4.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C34(H34A,H34B,H34C), C24(H24A,H24B,H24C), C24A(H24D,H24E,
 H24F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.56152(3) 0.73461(2) 0.55394(3) 0.02333(9) Uani 1 1 d . . . . .
O1 O 0.54116(19) 0.63771(16) 0.75857(17) 0.0332(4) Uani 1 1 d . . . . .
H1 H 0.494(3) 0.585(3) 0.784(3) 0.040(9) Uiso 1 1 d . . . . .
O2 O 0.74840(17) 0.77229(16) 0.49808(18) 0.0323(4) Uani 1 1 d . . . . .
H2 H 0.782(3) 0.833(3) 0.470(3) 0.075(13) Uiso 1 1 d . . . . .
O3 O 0.51505(17) 0.83411(15) 0.36916(16) 0.0296(4) Uani 1 1 d . . . . .
H3 H 0.549(2) 0.809(2) 0.328(2) 0.020(7) Uiso 1 1 d . . . . .
O4 O 0.42979(19) 0.40951(15) 0.68617(16) 0.0411(5) Uani 1 1 d . . . . .
O5 O 0.71264(15) 1.06418(14) 0.40562(16) 0.0338(4) Uani 1 1 d . . . . .
O44 O 0.37429(17) 0.45250(14) 0.84344(16) 0.0366(4) Uani 1 1 d . . . . .
O55 O 0.87690(17) 0.96385(14) 0.40892(19) 0.0454(5) Uani 1 1 d . . . . .
N1 N 0.5296(2) 0.86346(18) 0.6057(2) 0.0272(5) Uani 1 1 d . . . . .
H1A H 0.581(3) 0.923(3) 0.553(3) 0.045(9) Uiso 1 1 d . . . . .
H1B H 0.458(3) 0.883(2) 0.607(3) 0.048(9) Uiso 1 1 d . . . . .
N2 N 0.6143(2) 0.6002(2) 0.5157(2) 0.0281(5) Uani 1 1 d . . . . .
H2A H 0.612(3) 0.613(2) 0.445(3) 0.046(9) Uiso 1 1 d . . . . .
H2B H 0.573(3) 0.544(3) 0.566(3) 0.052(10) Uiso 1 1 d . . . . .
N3 N 0.3773(2) 0.6846(2) 0.6007(2) 0.0284(5) Uani 1 1 d . . . . .
H3A H 0.331(3) 0.716(2) 0.635(2) 0.036(8) Uiso 1 1 d . . . . .
H3B H 0.365(3) 0.619(3) 0.654(3) 0.049(9) Uiso 1 1 d . . . . .
N4 N 0.30400(18) 0.19637(15) 0.82337(17) 0.0234(4) Uani 1 1 d . . . . .
N5 N 0.87813(18) 1.26147(16) 0.27146(17) 0.0251(4) Uani 1 1 d . . . . .
C11 C 0.5379(3) 0.8341(2) 0.7242(2) 0.0398(7) Uani 1 1 d . . . . .
H11A H 0.495932 0.888213 0.755022 0.048 Uiso 1 1 calc R . . . .
H11B H 0.625188 0.841571 0.716425 0.048 Uiso 1 1 calc R . . . .
C12 C 0.4811(3) 0.7150(2) 0.8113(2) 0.0365(6) Uani 1 1 d . . . . .
H12 H 0.392464 0.709823 0.819922 0.044 Uiso 1 1 calc R . . . .
C13 C 0.4892(3) 0.6759(2) 0.9338(2) 0.0405(7) Uani 1 1 d . . . . .
H13A H 0.576233 0.669146 0.927198 0.049 Uiso 1 1 calc R . . . .
H13B H 0.444445 0.599944 0.982293 0.049 Uiso 1 1 calc R . . . .
C14 C 0.4382(3) 0.7522(2) 0.9984(3) 0.0413(7) Uani 1 1 d . . . . .
H14A H 0.495070 0.820262 0.963893 0.062 Uiso 1 1 calc GR . . . .
H14B H 0.428726 0.711739 1.080999 0.062 Uiso 1 1 calc GR . . . .
H14C H 0.358356 0.773070 0.991214 0.062 Uiso 1 1 calc GR . . . .
C31 C 0.3409(2) 0.6904(2) 0.5008(2) 0.0301(5) Uani 1 1 d . . . . .
H31A H 0.250688 0.676572 0.526493 0.036 Uiso 1 1 calc R . . . .
H31B H 0.377076 0.630991 0.475608 0.036 Uiso 1 1 calc R . . . .
C32 C 0.3851(2) 0.8071(2) 0.3963(2) 0.0318(6) Uani 1 1 d . . . . .
H32 H 0.340266 0.864146 0.422143 0.038 Uiso 1 1 calc R . . . .
C33 C 0.3535(3) 0.8131(2) 0.2908(3) 0.0420(7) Uani 1 1 d . . . . .
H33A H 0.264101 0.794293 0.315660 0.050 Uiso 1 1 calc R . . . .
H33B H 0.394855 0.755456 0.265352 0.050 Uiso 1 1 calc R . . . .
C34 C 0.3911(3) 0.9293(3) 0.1853(3) 0.0540(9) Uani 1 1 d . . . . .
H34A H 0.366813 0.927064 0.122302 0.081 Uiso 1 1 calc GR . . . .
H34B H 0.480008 0.947307 0.157618 0.081 Uiso 1 1 calc GR . . . .
H34C H 0.350062 0.987018 0.209248 0.081 Uiso 1 1 calc GR . . . .
C40 C 0.2371(2) 0.09004(19) 0.8937(2) 0.0242(5) Uani 1 1 d . . . . .
C41 C 0.2357(2) 0.01335(19) 0.8405(2) 0.0287(5) Uani 1 1 d . . . . .
H41 H 0.280558 0.034799 0.760045 0.034 Uiso 1 1 calc R . . . .
C42 C 0.1688(2) -0.0922(2) 0.9070(2) 0.0333(6) Uani 1 1 d . . . . .
H42 H 0.167572 -0.142091 0.871581 0.040 Uiso 1 1 calc R . . . .
C43 C 0.1017(3) -0.1254(2) 1.0288(2) 0.0362(6) Uani 1 1 d . . . . .
H43 H 0.056672 -0.197536 1.073302 0.043 Uiso 1 1 calc R . . . .
C44 C 0.1016(2) -0.0537(2) 1.0830(2) 0.0344(6) Uani 1 1 d . . . . .
H44 H 0.057299 -0.077281 1.163815 0.041 Uiso 1 1 calc R . . . .
C45 C 0.1688(2) 0.0566(2) 1.0160(2) 0.0276(5) Uani 1 1 d . . . . .
C46 C 0.1691(2) 0.1362(2) 1.0650(2) 0.0314(6) Uani 1 1 d . . . . .
H46 H 0.125389 0.116831 1.145335 0.038 Uiso 1 1 calc R . . . .
C47 C 0.2337(2) 0.2418(2) 0.9943(2) 0.0287(5) Uani 1 1 d . . . . .
H47 H 0.233369 0.295581 1.025594 0.034 Uiso 1 1 calc R . . . .
C48 C 0.3012(2) 0.26903(19) 0.8730(2) 0.0237(5) Uani 1 1 d . . . . .
C49 C 0.3752(2) 0.38681(19) 0.7937(2) 0.0272(5) Uani 1 1 d . . . . .
C50 C 0.9587(2) 1.35918(19) 0.2198(2) 0.0258(5) Uani 1 1 d . . . . .
C51 C 0.9199(3) 1.4649(2) 0.1551(2) 0.0342(6) Uani 1 1 d . . . . .
H51 H 0.840012 1.467291 0.150392 0.041 Uiso 1 1 calc R . . . .
C52 C 0.9995(3) 1.5626(2) 0.1000(3) 0.0423(7) Uani 1 1 d . . . . .
H52 H 0.973661 1.631478 0.057399 0.051 Uiso 1 1 calc R . . . .
C53 C 1.1203(3) 1.5609(2) 0.1066(3) 0.0437(7) Uani 1 1 d . . . . .
H53 H 1.174089 1.628387 0.067052 0.052 Uiso 1 1 calc R . . . .
C54 C 1.1593(3) 1.4621(2) 0.1700(3) 0.0374(6) Uani 1 1 d . . . . .
H54 H 1.239036 1.462264 0.174549 0.045 Uiso 1 1 calc R . . . .
C55 C 1.0792(2) 1.3589(2) 0.2290(2) 0.0280(5) Uani 1 1 d . . . . .
C56 C 1.1134(2) 1.2537(2) 0.2977(2) 0.0323(6) Uani 1 1 d . . . . .
H56 H 1.190516 1.250401 0.308325 0.039 Uiso 1 1 calc R . . . .
C57 C 1.0328(2) 1.1568(2) 0.3485(2) 0.0282(5) Uani 1 1 d . . . . .
H57 H 1.054719 1.086780 0.393375 0.034 Uiso 1 1 calc R . . . .
C58 C 0.9154(2) 1.16381(19) 0.3322(2) 0.0228(5) Uani 1 1 d . . . . .
C59 C 0.8264(2) 1.0561(2) 0.3863(2) 0.0272(5) Uani 1 1 d . . . . .
C21 C 0.7466(4) 0.5887(3) 0.5012(5) 0.0291(9) Uani 0.757(6) 1 d . . P A 1
H21A H 0.778252 0.541036 0.458109 0.035 Uiso 0.757(6) 1 calc R . P A 1
H21B H 0.755795 0.551761 0.578754 0.035 Uiso 0.757(6) 1 calc R . P A 1
C22 C 0.8204(3) 0.7046(3) 0.4341(4) 0.0244(9) Uani 0.757(6) 1 d . . P A 1
H22 H 0.819835 0.737340 0.352258 0.029 Uiso 0.757(6) 1 calc R . P A 1
C23 C 0.9539(3) 0.7025(3) 0.4319(3) 0.0305(10) Uani 0.757(6) 1 d . . P A 1
H23A H 0.953984 0.664365 0.512860 0.037 Uiso 0.757(6) 1 calc R . P A 1
H23B H 0.991355 0.780764 0.399537 0.037 Uiso 0.757(6) 1 calc R . P A 1
C24 C 1.0332(4) 0.6418(5) 0.3584(5) 0.0361(11) Uani 0.757(6) 1 d . . P A 1
H24A H 1.033164 0.678763 0.278199 0.054 Uiso 0.757(6) 1 calc GR . P A 1
H24B H 0.999302 0.563118 0.392413 0.054 Uiso 0.757(6) 1 calc GR . P A 1
H24C H 1.117371 0.645160 0.358169 0.054 Uiso 0.757(6) 1 calc GR . P A 1
C21A C 0.7297(12) 0.5685(10) 0.5641(12) 0.024(3) Uani 0.243(6) 1 d . . P A 2
H21C H 0.701209 0.543414 0.649856 0.029 Uiso 0.243(6) 1 calc R . P A 2
H21D H 0.771199 0.508007 0.544238 0.029 Uiso 0.243(6) 1 calc R . P A 2
C22A C 0.8180(10) 0.6790(9) 0.5021(12) 0.026(3) Uani 0.243(6) 1 d . . P A 2
H22A H 0.875010 0.674575 0.545511 0.032 Uiso 0.243(6) 1 calc R . P A 2
C23A C 0.8911(12) 0.7125(9) 0.3733(11) 0.034(3) Uani 0.243(6) 1 d . . P A 2
H23C H 0.929235 0.790767 0.339075 0.041 Uiso 0.243(6) 1 calc R . P A 2
H23D H 0.834243 0.710692 0.332527 0.041 Uiso 0.243(6) 1 calc R . P A 2
C24A C 0.9928(15) 0.635(2) 0.351(2) 0.0361(11) Uani 0.243(6) 1 d . . P A 2
H24D H 1.054761 0.675513 0.274081 0.054 Uiso 0.243(6) 1 calc GR . P A 2
H24E H 0.956693 0.567311 0.354463 0.054 Uiso 0.243(6) 1 calc GR . P A 2
H24F H 1.031140 0.614966 0.411130 0.054 Uiso 0.243(6) 1 calc GR . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 2.3824(18) . ?
Cu1 O2 2.0191(19) . ?
Cu1 N1 1.9982(19) . ?
Cu1 N2 1.9945(19) . ?
Cu1 N3 2.035(2) . ?
O1 C12 1.449(3) . ?
O2 C22 1.481(4) . ?
O2 C22A 1.398(10) . ?
O3 C32 1.427(3) . ?
O4 C49 1.246(3) . ?
O5 C59 1.244(3) . ?
O44 C49 1.249(3) . ?
O55 C59 1.260(3) . ?
N1 C11 1.472(3) . ?
N2 C21 1.464(4) . ?
N2 C21A 1.609(12) . ?
N3 C31 1.468(3) . ?
N4 C40 1.378(3) . ?
N4 C48 1.324(3) . ?
N5 C50 1.369(3) . ?
N5 C58 1.323(3) . ?
C11 C12 1.496(4) . ?
C12 C13 1.505(4) . ?
C13 C14 1.515(3) . ?
C31 C32 1.523(4) . ?
C32 C33 1.506(4) . ?
C33 C34 1.521(4) . ?
C40 C41 1.415(3) . ?
C40 C45 1.412(3) . ?
C41 C42 1.367(3) . ?
C42 C43 1.405(4) . ?
C43 C44 1.365(4) . ?
C44 C45 1.415(3) . ?
C45 C46 1.405(3) . ?
C46 C47 1.363(3) . ?
C47 C48 1.413(3) . ?
C48 C49 1.527(3) . ?
C50 C51 1.420(3) . ?
C50 C55 1.417(3) . ?
C51 C52 1.359(4) . ?
C52 C53 1.406(4) . ?
C53 C54 1.354(4) . ?
C54 C55 1.411(4) . ?
C55 C56 1.409(3) . ?
C56 C57 1.362(4) . ?
C57 C58 1.416(3) . ?
C58 C59 1.514(3) . ?
C21 C22 1.500(5) . ?
C22 C23 1.511(5) . ?
C23 C24 1.520(6) . ?
C21A C22A 1.526(16) . ?
C22A C23A 1.493(17) . ?
C23A C24A 1.52(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O1 94.12(8) . . ?
O2 Cu1 N3 173.57(8) . . ?
N1 Cu1 O1 79.02(7) . . ?
N1 Cu1 O2 91.72(9) . . ?
N1 Cu1 N3 94.58(10) . . ?
N2 Cu1 O1 94.62(9) . . ?
N2 Cu1 O2 81.65(8) . . ?
N2 Cu1 N1 170.53(9) . . ?
N2 Cu1 N3 92.23(9) . . ?
N3 Cu1 O1 88.30(8) . . ?
C12 O1 Cu1 104.38(13) . . ?
C22 O2 Cu1 113.34(17) . . ?
C22A O2 Cu1 114.9(5) . . ?
C11 N1 Cu1 113.22(15) . . ?
C21 N2 Cu1 110.37(19) . . ?
C21A N2 Cu1 101.1(4) . . ?
C31 N3 Cu1 113.73(16) . . ?
C48 N4 C40 118.1(2) . . ?
C58 N5 C50 118.1(2) . . ?
N1 C11 C12 113.0(2) . . ?
O1 C12 C11 107.1(2) . . ?
O1 C12 C13 109.2(2) . . ?
C11 C12 C13 116.7(2) . . ?
C12 C13 C14 116.0(2) . . ?
N3 C31 C32 111.0(2) . . ?
O3 C32 C31 109.30(19) . . ?
O3 C32 C33 113.3(2) . . ?
C33 C32 C31 111.9(2) . . ?
C32 C33 C34 114.2(2) . . ?
N4 C40 C41 118.5(2) . . ?
N4 C40 C45 122.1(2) . . ?
C45 C40 C41 119.4(2) . . ?
C42 C41 C40 120.2(2) . . ?
C41 C42 C43 120.2(2) . . ?
C44 C43 C42 121.1(2) . . ?
C43 C44 C45 120.0(2) . . ?
C40 C45 C44 119.2(2) . . ?
C46 C45 C40 117.9(2) . . ?
C46 C45 C44 122.9(2) . . ?
C47 C46 C45 119.6(2) . . ?
C46 C47 C48 119.4(2) . . ?
N4 C48 C47 122.9(2) . . ?
N4 C48 C49 117.5(2) . . ?
C47 C48 C49 119.6(2) . . ?
O4 C49 O44 125.8(2) . . ?
O4 C49 C48 117.9(2) . . ?
O44 C49 C48 116.3(2) . . ?
N5 C50 C51 118.8(2) . . ?
N5 C50 C55 122.4(2) . . ?
C55 C50 C51 118.7(2) . . ?
C52 C51 C50 120.0(3) . . ?
C51 C52 C53 120.9(2) . . ?
C54 C53 C52 120.7(3) . . ?
C53 C54 C55 120.2(3) . . ?
C54 C55 C50 119.5(2) . . ?
C56 C55 C50 117.6(2) . . ?
C56 C55 C54 123.0(2) . . ?
C57 C56 C55 119.6(2) . . ?
C56 C57 C58 119.4(2) . . ?
N5 C58 C57 122.9(2) . . ?
N5 C58 C59 117.4(2) . . ?
C57 C58 C59 119.63(19) . . ?
O5 C59 O55 125.6(2) . . ?
O5 C59 C58 119.38(19) . . ?
O55 C59 C58 115.1(2) . . ?
N2 C21 C22 110.1(3) . . ?
O2 C22 C21 103.2(3) . . ?
O2 C22 C23 111.8(3) . . ?
C21 C22 C23 113.5(3) . . ?
C22 C23 C24 113.1(3) . . ?
C22A C21A N2 105.3(7) . . ?
O2 C22A C21A 109.5(8) . . ?
O2 C22A C23A 101.7(9) . . ?
C23A C22A C21A 116.0(10) . . ?
C22A C23A C24A 113.6(12) . . ?

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
_geom_hbond_publ_flag
O1 H1 O44 0.77(3) 1.94(3) 2.710(3) 178(3) . yes
O2 H2 O55 0.76(4) 1.77(4) 2.529(3) 173(4) . yes
O3 H3 N4 0.74(2) 2.15(3) 2.832(3) 155(3) 2_666 yes
N1 H1A O5 0.86(3) 2.18(3) 3.040(3) 174(3) . yes
N1 H1B O5 0.83(3) 2.07(3) 2.904(3) 175(3) 2_676 yes
N2 H2A O4 0.88(3) 2.05(3) 2.889(3) 161(3) 2_666 yes
N2 H2B O4 0.78(3) 2.11(3) 2.883(3) 167(3) . yes
N3 H3A N5 0.78(3) 2.36(3) 3.046(3) 147(3) 2_676 yes

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.026
_oxdiff_exptl_absorpt_empirical_full_min 0.382
####################################################################### 
# 
# 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_11a
_database_code_depnum_ccdc_archive 'CCDC 2077007'
loop_
_audit_author_name
_audit_author_address
'Barbara Modec'
;University of Ljubljana
Slovenia
;
_audit_update_record             
;
2021-04-12 deposited with the CCDC.	2022-03-18 downloaded from the CCDC.
;
_audit_creation_date             2021-03-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H30 Cu N4 O6'
_chemical_formula_sum            'C26 H30 Cu N4 O6'
_chemical_formula_weight         558.08
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.6066(3)
_cell_length_b                   10.4353(6)
_cell_length_c                   11.2830(7)
_cell_angle_alpha                104.885(5)
_cell_angle_beta                 95.480(5)
_cell_angle_gamma                99.643(4)
_cell_volume                     622.28(6)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2953
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      74.9260
_cell_measurement_theta_min      4.0490
_shelx_estimated_absorpt_T_max   0.936
_shelx_estimated_absorpt_T_min   0.435
_exptl_absorpt_coefficient_mu    1.662
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.19594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.489
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             291
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0235
_diffrn_reflns_av_unetI/netI     0.0249
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4819
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.088
_diffrn_reflns_theta_min         4.098
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4933
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -116.00 -17.00   1.00    2.00    --  -41.57 -37.00 -30.00   99
  2  ω   -115.00 -29.00   1.00    2.00    --  -41.57 -37.00-120.00   86
  3  ω      1.00  67.00   1.00    2.00    --   41.57 -99.00-150.00   66
  4  ω      2.00  58.00   1.00    2.00    --   41.57 -99.00 120.00   56
  5  ω     47.00  79.00   1.00    2.00    --   41.57-125.00  30.00   32
  6  ω     27.00  92.00   1.00    8.00    --  109.50 -94.00-180.00   65
  7  ω     99.00 141.00   1.00    8.00    --  109.50 -77.00-180.00   42
  8  ω     41.00  77.00   1.00    8.00    --  109.50 -45.00   0.00   36
  9  ω     28.00  76.00   1.00    8.00    --  109.50 -94.00  30.00   48
 10  ω    107.00 159.00   1.00    8.00    --  109.50  45.00 -90.00   52
 11  ω     28.00 106.00   1.00    8.00    --  109.50 -94.00  90.00   78
 12  ω     73.00 117.00   1.00    8.00    --  109.50-125.00 -90.00   44
 13  ω     37.00  68.00   1.00    8.00    --  109.50 -77.00-180.00   31
 14  ω     86.00 118.00   1.00    8.00    --  109.50-125.00   0.00   32
 15  ω     37.00  62.00   1.00    8.00    --  109.50-125.00  90.00   25
 16  ω     68.00  94.00   1.00    8.00    --  109.50-125.00-180.00   26
 17  ω     36.00  99.00   1.00    8.00    --  109.50 -45.00-180.00   63
 18  ω     82.00 118.00   1.00    8.00    --  109.50-125.00  90.00   36
 19  ω     99.00 126.00   1.00    8.00    --  109.50  30.00 120.00   27
 20  ω    135.00 177.00   1.00    8.00    --  109.50  30.00 120.00   42
 21  ω    102.00 133.00   1.00    8.00    --  109.50 -45.00   0.00   31
 22  ω     88.00 173.00   1.00    8.00    --  109.50  30.00-180.00   85
 23  ω     38.00 104.00   1.00    8.00    --  109.50-125.00  30.00   66
 24  ω     85.00 154.00   1.00    8.00    --  109.50 -15.00  90.00   69
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0747092000
_diffrn_orient_matrix_UB_12      -0.0901726000
_diffrn_orient_matrix_UB_13      -0.1158150000
_diffrn_orient_matrix_UB_21      -0.2200571000
_diffrn_orient_matrix_UB_22      0.0203738000
_diffrn_orient_matrix_UB_23      -0.0809118000
_diffrn_orient_matrix_UB_31      0.1592211000
_diffrn_orient_matrix_UB_32      0.1255253000
_diffrn_orient_matrix_UB_33      -0.0207547000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2437
_reflns_number_total             2524
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     73.11
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.621
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     181
_refine_ls_number_reflns         2524
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0350
_refine_ls_R_factor_gt           0.0340
_refine_ls_restrained_S_all      1.047
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0536P)²+0.3761P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0921
_refine_ls_wR_factor_ref         0.0933
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.500000 0.500000 0.500000 0.01675(13) Uani 1 2 d S T P . .
O1 O 0.7541(2) 0.47417(12) 0.38747(10) 0.0191(2) Uani 1 1 d . . . . .
O2 O 0.0675(3) 0.72167(15) 0.02248(13) 0.0349(3) Uani 1 1 d . . . . .
H2 H 0.072(5) 0.705(3) -0.050(3) 0.045(8) Uiso 1 1 d . . . . .
O11 O 0.8751(2) 0.35611(13) 0.21962(11) 0.0253(3) Uani 1 1 d . . . . .
N1 N 0.3610(3) 0.27441(14) 0.36175(13) 0.0179(3) Uani 1 1 d . . . . .
N2 N 0.3026(3) 0.57864(16) 0.38773(13) 0.0187(3) Uani 1 1 d . . . . .
H2A H 0.169(5) 0.540(2) 0.384(2) 0.018(5) Uiso 1 1 d . . . . .
H2B H 0.309(5) 0.661(3) 0.433(2) 0.033(6) Uiso 1 1 d . . . . .
C10 C 0.1597(3) 0.17493(16) 0.34929(16) 0.0188(3) Uani 1 1 d . . . . .
C11 C 0.0186(3) 0.18428(18) 0.44767(17) 0.0231(3) Uani 1 1 d . . . . .
H11 H 0.063059 0.256889 0.518688 0.028 Uiso 1 1 calc R . . . .
C12 C -0.1836(3) 0.08607(19) 0.43793(19) 0.0278(4) Uani 1 1 d . . . . .
H12 H -0.276424 0.092687 0.502478 0.033 Uiso 1 1 calc R . . . .
C13 C -0.2524(3) -0.02495(19) 0.3311(2) 0.0299(4) Uani 1 1 d . . . . .
H13 H -0.390659 -0.090462 0.325856 0.036 Uiso 1 1 calc R . . . .
C14 C -0.1183(3) -0.03757(18) 0.23505(19) 0.0271(4) Uani 1 1 d . . . . .
H14 H -0.164661 -0.111710 0.165400 0.032 Uiso 1 1 calc R . . . .
C15 C 0.0919(3) 0.06289(17) 0.24193(16) 0.0214(3) Uani 1 1 d . . . . .
C16 C 0.2385(3) 0.05675(18) 0.14617(17) 0.0253(4) Uani 1 1 d . . . . .
H16 H 0.198169 -0.014387 0.073886 0.030 Uiso 1 1 calc R . . . .
C17 C 0.4404(3) 0.15648(18) 0.16090(16) 0.0240(4) Uani 1 1 d . . . . .
H17 H 0.539562 0.153808 0.099141 0.029 Uiso 1 1 calc R . . . .
C18 C 0.4954(3) 0.26321(16) 0.27110(15) 0.0182(3) Uani 1 1 d . . . . .
C19 C 0.7255(3) 0.37252(17) 0.29286(15) 0.0182(3) Uani 1 1 d . . . . .
C21 C 0.3601(3) 0.58718(18) 0.26492(15) 0.0216(3) Uani 1 1 d . . . . .
H21A H 0.350705 0.496588 0.211916 0.026 Uiso 1 1 calc R . . . .
H21B H 0.526476 0.636720 0.273835 0.026 Uiso 1 1 calc R . . . .
C22 C 0.1871(3) 0.65688(18) 0.20330(16) 0.0221(3) Uani 1 1 d . . . . .
H22A H 0.019958 0.610092 0.198044 0.027 Uiso 1 1 calc R . . . .
H22B H 0.202654 0.749095 0.254078 0.027 Uiso 1 1 calc R . . . .
C23 C 0.2398(4) 0.6588(2) 0.07456(16) 0.0272(4) Uani 1 1 d . . . . .
H23A H 0.404351 0.708538 0.078970 0.033 Uiso 1 1 calc R . . . .
H23B H 0.227139 0.567063 0.023198 0.033 Uiso 1 1 calc R . . . .


_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 O1 2.0034(11) . ?
Cu1 O1 2.0034(11) 2_666 ?
Cu1 N1 2.4184(14) 2_666 ?
Cu1 N1 2.4185(14) . ?
Cu1 N2 2.0184(14) . ?
Cu1 N2 2.0184(14) 2_666 ?
O1 C19 1.272(2) . ?
O2 C23 1.418(2) . ?
O11 C19 1.234(2) . ?
N1 C10 1.369(2) . ?
N1 C18 1.320(2) . ?
N2 C21 1.474(2) . ?
C10 C11 1.416(2) . ?
C10 C15 1.419(2) . ?
C11 C12 1.370(3) . ?
C12 C13 1.410(3) . ?
C13 C14 1.368(3) . ?
C14 C15 1.422(2) . ?
C15 C16 1.414(3) . ?
C16 C17 1.368(3) . ?
C17 C18 1.408(2) . ?
C18 C19 1.526(2) . ?
C21 C22 1.524(2) . ?
C22 C23 1.514(2) . ?

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 Cu1 O1 180.0 . 2_666 ?
O1 Cu1 N1 74.77(5) . . ?
O1 Cu1 N1 105.23(5) 2_666 . ?
O1 Cu1 N1 105.23(5) . 2_666 ?
O1 Cu1 N1 74.77(5) 2_666 2_666 ?
O1 Cu1 N2 93.09(5) . . ?
O1 Cu1 N2 86.91(5) . 2_666 ?
O1 Cu1 N2 93.09(5) 2_666 2_666 ?
O1 Cu1 N2 86.91(5) 2_666 . ?
N1 Cu1 N1 180.0 2_666 . ?
N2 Cu1 N1 88.61(5) 2_666 . ?
N2 Cu1 N1 88.61(5) . 2_666 ?
N2 Cu1 N1 91.39(5) . . ?
N2 Cu1 N1 91.39(5) 2_666 2_666 ?
N2 Cu1 N2 180.0 . 2_666 ?
C19 O1 Cu1 122.37(10) . . ?
C10 N1 Cu1 133.61(11) . . ?
C18 N1 Cu1 107.04(10) . . ?
C18 N1 C10 118.18(15) . . ?
C21 N2 Cu1 123.86(11) . . ?
N1 C10 C11 118.49(16) . . ?
N1 C10 C15 121.86(15) . . ?
C11 C10 C15 119.64(16) . . ?
C12 C11 C10 119.80(17) . . ?
C11 C12 C13 120.71(17) . . ?
C14 C13 C12 120.86(17) . . ?
C13 C14 C15 119.86(18) . . ?
C10 C15 C14 119.12(16) . . ?
C16 C15 C10 117.91(16) . . ?
C16 C15 C14 122.97(17) . . ?
C17 C16 C15 119.35(16) . . ?
C16 C17 C18 118.89(16) . . ?
N1 C18 C17 123.79(15) . . ?
N1 C18 C19 116.05(14) . . ?
C17 C18 C19 120.14(15) . . ?
O1 C19 C18 117.75(14) . . ?
O11 C19 O1 123.84(15) . . ?
O11 C19 C18 118.40(15) . . ?
N2 C21 C22 112.47(14) . . ?
C23 C22 C21 112.00(15) . . ?
O2 C23 C22 108.52(15) . . ?

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
_geom_hbond_publ_flag
O2 H2 O11 0.79(3) 1.93(3) 2.7094(19) 169(3) 2_665 yes

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.423
_oxdiff_exptl_absorpt_empirical_full_min 0.370
####################################################################### 
# 
# 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_anti11d4MeOH
_database_code_depnum_ccdc_archive 'CCDC 2077014'
loop_
_audit_author_name
_audit_author_address
'Barbara Modec'
;University of Ljubljana
Slovenia
;
_audit_update_record             
;
2021-04-12 deposited with the CCDC.	2022-03-18 downloaded from the CCDC.
;
_audit_creation_date             2021-03-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C26 H28 Cu2 N4 O6, 4(C H4 O)'
_chemical_formula_sum            'C30 H44 Cu2 N4 O10'
_chemical_formula_weight         747.77
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_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                   10.9996(4)
_cell_length_b                   12.0720(3)
_cell_length_c                   12.8700(4)
_cell_angle_alpha                90
_cell_angle_beta                 107.881(3)
_cell_angle_gamma                90
_cell_volume                     1626.42(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8076
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      30.1800
_cell_measurement_theta_min      3.6910
_shelx_estimated_absorpt_T_max   0.771
_shelx_estimated_absorpt_T_min   0.726
_exptl_absorpt_coefficient_mu    1.369
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83383
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            blue
_exptl_crystal_density_diffrn    1.527
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             780
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_unetI/netI     0.0245
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.905
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            16107
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.367
_diffrn_reflns_theta_min         2.922
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector_area_resol_mean 10.4933
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.905
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -16.00   27.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.2075  -99.0000  -30.0000 43

#__ type_ start__ end____ width___ exp.time_
  2 omega  -11.00   80.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       14.3637   37.0000  -90.0000 91

#__ type_ start__ end____ width___ exp.time_
  3 omega    3.00   87.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       14.3637   57.0000  -30.0000 84

#__ type_ start__ end____ width___ exp.time_
  4 omega  -12.00   49.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       14.3637  -99.0000   60.0000 61

#__ type_ start__ end____ width___ exp.time_
  5 omega  -44.00   48.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       14.3637  -77.0000  120.0000 92
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0269221000
_diffrn_orient_matrix_UB_12      0.0509592000
_diffrn_orient_matrix_UB_13      -0.0094852000
_diffrn_orient_matrix_UB_21      -0.0387059000
_diffrn_orient_matrix_UB_22      -0.0013089000
_diffrn_orient_matrix_UB_23      -0.0553606000
_diffrn_orient_matrix_UB_31      -0.0486602000
_diffrn_orient_matrix_UB_32      0.0292137000
_diffrn_orient_matrix_UB_33      0.0140734000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3901
_reflns_number_total             4433
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.50
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.469
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     226
_refine_ls_number_reflns         4433
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0264
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0247P)²+1.1057P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0634
_refine_ls_wR_factor_ref         0.0674
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 O3-H3
 0.75 with sigma of 0.01
3.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B)
3.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14), C16(H16), C17(H17)
3.c Idealised Me refined as rotating group:
 C31(H31A,H31B,H31C), C41(H41A,H41B,H41C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.53543(2) 0.60552(2) 0.45230(2) 0.01250(6) Uani 1 1 d . . . . .
O1 O 0.46108(10) 0.60074(8) 0.27090(9) 0.0178(2) Uani 1 1 d . . . . .
O2 O 0.60971(10) 0.46964(8) 0.52065(9) 0.0169(2) Uani 1 1 d . . . . .
O3 O 0.57910(16) 0.42196(14) 0.20458(14) 0.0518(5) Uani 1 1 d D . . . .
H3 H 0.540(2) 0.4667(16) 0.218(2) 0.044(7) Uiso 1 1 d D . . . .
O4 O 0.80868(15) 0.30423(12) 0.25534(11) 0.0335(3) Uani 1 1 d . . . . .
H4 H 0.750(2) 0.3364(19) 0.2521(19) 0.033(6) Uiso 1 1 d . . . . .
O11 O 0.33646(12) 0.70185(10) 0.13401(10) 0.0281(3) Uani 1 1 d . . . . .
N1 N 0.44360(12) 0.75221(10) 0.41836(10) 0.0149(2) Uani 1 1 d . . . . .
N2 N 0.70048(12) 0.66879(11) 0.44441(11) 0.0159(2) Uani 1 1 d . . . . .
H2A H 0.7366(19) 0.7040(16) 0.5028(17) 0.023(5) Uiso 1 1 d . . . . .
H2B H 0.680(2) 0.7154(17) 0.3921(18) 0.027(5) Uiso 1 1 d . . . . .
C10 C 0.43442(14) 0.82582(12) 0.49697(13) 0.0172(3) Uani 1 1 d . . . . .
C11 C 0.50322(16) 0.80572(13) 0.60721(14) 0.0221(3) Uani 1 1 d . . . . .
H11 H 0.554209 0.742934 0.626299 0.026 Uiso 1 1 calc R . . . .
C12 C 0.49495(18) 0.87872(15) 0.68623(15) 0.0282(4) Uani 1 1 d . . . . .
H12 H 0.541153 0.865448 0.758808 0.034 Uiso 1 1 calc R . . . .
C13 C 0.41695(18) 0.97402(14) 0.65870(16) 0.0296(4) Uani 1 1 d . . . . .
H13 H 0.412404 1.023025 0.713140 0.036 Uiso 1 1 calc R . . . .
C14 C 0.34845(16) 0.99440(13) 0.55285(16) 0.0269(4) Uani 1 1 d . . . . .
H14 H 0.296818 1.056958 0.535519 0.032 Uiso 1 1 calc R . . . .
C15 C 0.35525(15) 0.92084(12) 0.46870(14) 0.0207(3) Uani 1 1 d . . . . .
C16 C 0.28650(15) 0.93713(13) 0.35798(15) 0.0243(3) Uani 1 1 d . . . . .
H16 H 0.232951 0.998156 0.336999 0.029 Uiso 1 1 calc R . . . .
C17 C 0.29851(15) 0.86298(13) 0.28103(14) 0.0218(3) Uani 1 1 d . . . . .
H17 H 0.254039 0.873725 0.207623 0.026 Uiso 1 1 calc R . . . .
C18 C 0.37897(14) 0.77033(12) 0.31438(12) 0.0166(3) Uani 1 1 d . . . . .
C19 C 0.39327(14) 0.68406(12) 0.23164(12) 0.0179(3) Uani 1 1 d . . . . .
C21 C 0.79315(15) 0.58846(13) 0.42564(14) 0.0209(3) Uani 1 1 d . . . . .
H21A H 0.870135 0.627300 0.425052 0.025 Uiso 1 1 calc R . . . .
H21B H 0.756947 0.553812 0.354840 0.025 Uiso 1 1 calc R . . . .
C22 C 0.82698(15) 0.49993(13) 0.51328(15) 0.0231(3) Uani 1 1 d . . . . .
H22A H 0.850929 0.535462 0.584292 0.028 Uiso 1 1 calc R . . . .
H22B H 0.900612 0.459046 0.507636 0.028 Uiso 1 1 calc R . . . .
C23 C 0.71883(15) 0.41881(13) 0.50607(15) 0.0225(3) Uani 1 1 d . . . . .
H23A H 0.695086 0.382911 0.435233 0.027 Uiso 1 1 calc R . . . .
H23B H 0.749076 0.361969 0.561256 0.027 Uiso 1 1 calc R . . . .
C31 C 0.5088(2) 0.38083(19) 0.10290(18) 0.0419(5) Uani 1 1 d . . . . .
H31A H 0.456819 0.438877 0.060782 0.063 Uiso 1 1 calc GR . . . .
H31B H 0.455107 0.321455 0.112334 0.063 Uiso 1 1 calc GR . . . .
H31C H 0.566023 0.353784 0.065424 0.063 Uiso 1 1 calc GR . . . .
C41 C 0.84038(19) 0.23423(16) 0.34741(16) 0.0324(4) Uani 1 1 d . . . . .
H41A H 0.884432 0.170085 0.333283 0.049 Uiso 1 1 calc GR . . . .
H41B H 0.763748 0.211568 0.362337 0.049 Uiso 1 1 calc GR . . . .
H41C H 0.894545 0.273348 0.409338 0.049 Uiso 1 1 calc GR . . . .


_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 Cu1 3.0320(3) 3_666 ?
Cu1 O1 2.2248(11) . ?
Cu1 O2 1.9581(10) 3_666 ?
Cu1 O2 1.9211(10) . ?
Cu1 N1 2.0189(12) . ?
Cu1 N2 2.0007(13) . ?
O1 C19 1.2617(18) . ?
O2 C23 1.4110(18) . ?
O3 C31 1.391(3) . ?
O4 C41 1.409(2) . ?
O11 C19 1.2383(19) . ?
N1 C10 1.3734(19) . ?
N1 C18 1.3266(19) . ?
N2 C21 1.4796(19) . ?
C10 C11 1.409(2) . ?
C10 C15 1.418(2) . ?
C11 C12 1.370(2) . ?
C12 C13 1.414(3) . ?
C13 C14 1.362(3) . ?
C14 C15 1.420(2) . ?
C15 C16 1.407(2) . ?
C16 C17 1.371(2) . ?
C17 C18 1.409(2) . ?
C18 C19 1.532(2) . ?
C21 C22 1.515(2) . ?
C22 C23 1.522(2) . ?

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 Cu1 Cu1 110.23(3) . 3_666 ?
O2 Cu1 Cu1 39.03(3) . 3_666 ?
O2 Cu1 Cu1 38.16(3) 3_666 3_666 ?
O2 Cu1 O1 96.74(4) 3_666 . ?
O2 Cu1 O1 115.21(4) . . ?
O2 Cu1 O2 77.19(5) . 3_666 ?
O2 Cu1 N1 93.66(5) 3_666 . ?
O2 Cu1 N1 164.19(5) . . ?
O2 Cu1 N2 94.84(5) . . ?
O2 Cu1 N2 171.10(5) 3_666 . ?
N1 Cu1 Cu1 130.61(4) . 3_666 ?
N1 Cu1 O1 78.31(4) . . ?
N2 Cu1 Cu1 133.75(4) . 3_666 ?
N2 Cu1 O1 90.20(5) . . ?
N2 Cu1 N1 93.19(5) . . ?
C19 O1 Cu1 112.41(9) . . ?
Cu1 O2 Cu1 102.81(5) . 3_666 ?
C23 O2 Cu1 124.74(9) . . ?
C23 O2 Cu1 126.55(9) . 3_666 ?
C10 N1 Cu1 123.59(10) . . ?
C18 N1 Cu1 116.13(10) . . ?
C18 N1 C10 119.90(13) . . ?
C21 N2 Cu1 116.07(10) . . ?
N1 C10 C11 119.48(13) . . ?
N1 C10 C15 120.83(14) . . ?
C11 C10 C15 119.69(14) . . ?
C12 C11 C10 119.95(15) . . ?
C11 C12 C13 120.73(17) . . ?
C14 C13 C12 120.31(16) . . ?
C13 C14 C15 120.50(16) . . ?
C10 C15 C14 118.82(16) . . ?
C16 C15 C10 118.01(15) . . ?
C16 C15 C14 123.18(15) . . ?
C17 C16 C15 119.95(14) . . ?
C16 C17 C18 119.28(15) . . ?
N1 C18 C17 122.01(14) . . ?
N1 C18 C19 116.84(13) . . ?
C17 C18 C19 121.13(14) . . ?
O1 C19 C18 115.97(13) . . ?
O11 C19 O1 126.63(15) . . ?
O11 C19 C18 117.39(14) . . ?
N2 C21 C22 111.40(13) . . ?
C21 C22 C23 113.57(14) . . ?
O2 C23 C22 113.15(13) . . ?

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
_geom_hbond_publ_flag
O3 H3 O1 0.744(10) 2.048(11) 2.7843(18) 171(3) . yes
O4 H4 O3 0.74(2) 2.07(2) 2.795(2) 167(2) . yes
N2 H2A O11 0.85(2) 2.05(2) 2.8964(18) 173.3(19) 4_676 yes
N2 H2B O4 0.85(2) 2.22(2) 3.0221(19) 157.8(19) 2_655 yes

