# 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 2018

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1851678'
_audit_update_record             
;
2018-10-08 deposited with the CCDC.
2018-11-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H20 Cu N5 O12 Tb'
_chemical_formula_sum            'C19 H20 Cu N5 O12 Tb'
_chemical_formula_weight         732.88

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Tb Tb -0.1723 4.1537 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.121(5)
_cell_length_b                   14.240(5)
_cell_length_c                   16.074(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.293(5)
_cell_angle_gamma                90.00
_cell_volume                     2416.9(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4396
_cell_measurement_theta_min      1.96
_cell_measurement_theta_max      25.28

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.014
_exptl_crystal_F_000             1436
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    3.856
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   EMPIRICAL
_exptl_absorpt_correction_T_min  0.831
_exptl_absorpt_correction_T_max  0.891
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15532
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_av_R_equivalents  0.0470
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.956
_diffrn_reflns_theta_max         25.278
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             4395
_reflns_number_gt                3121
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0500P)²+10.9966P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4324
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1187
_refine_ls_wR_factor_gt          0.0986
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Tb1 Tb 1.16411(3) 0.31795(3) 0.82065(2) 0.03661(15) Uani 1 1 d . . . . .
Cu1 Cu 0.87456(8) 0.37777(7) 0.83050(6) 0.0369(2) Uani 1 1 d . . . . .
O1 O 0.9684(5) 0.3877(4) 0.7490(3) 0.0412(13) Uani 1 1 d . . . . .
O3 O 1.2831(4) 0.3279(4) 0.9814(3) 0.0428(13) Uani 1 1 d . . . . .
O2 O 1.0420(4) 0.3514(4) 0.9095(3) 0.0397(13) Uani 1 1 d . . . . .
O12 O 1.3633(5) 0.3970(5) 0.8349(5) 0.0631(18) Uani 1 1 d . . . . .
O10 O 1.2165(5) 0.4829(4) 0.8521(4) 0.0551(16) Uani 1 1 d . . . . .
O6 O 1.1649(6) 0.3139(5) 0.6726(4) 0.0626(18) Uani 1 1 d . . . . .
O4 O 1.2959(6) 0.2204(5) 0.7587(5) 0.0631(18) Uani 1 1 d . . . . .
O9 O 1.1781(7) 0.1639(5) 0.8900(4) 0.0677(19) Uani 1 1 d . . . . .
O7 O 1.0207(6) 0.1866(5) 0.7763(4) 0.0666(19) Uani 1 1 d . . . . .
N2 N 0.8074(6) 0.3858(5) 0.9275(4) 0.0387(15) Uani 1 1 d . . . . .
N1 N 0.7132(6) 0.3686(5) 0.7350(4) 0.0416(16) Uani 1 1 d . . . . .
C18 C 1.0852(7) 0.3671(5) 0.9945(5) 0.0353(17) Uani 1 1 d . . . . .
N3 N 1.2552(8) 0.2571(6) 0.6832(5) 0.057(2) Uani 1 1 d . . . . .
C17 C 1.2175(7) 0.3578(6) 1.0375(5) 0.0394(18) Uani 1 1 d . . . . .
C13 C 1.0086(7) 0.3932(5) 1.0451(5) 0.0374(18) Uani 1 1 d . . . . .
C1 C 0.9261(8) 0.4446(6) 0.6796(5) 0.0421(19) Uani 1 1 d . . . . .
N4 N 1.0783(9) 0.1323(6) 0.8370(6) 0.071(2) Uani 1 1 d . . . . .
N5 N 1.3311(7) 0.4763(6) 0.8550(5) 0.058(2) Uani 1 1 d . . . . .
O11 O 1.4030(7) 0.5419(6) 0.8751(7) 0.105(3) Uani 1 1 d . . . . .
C14 C 1.0632(8) 0.4096(6) 1.1344(5) 0.045(2) Uani 1 1 d . . . . .
H14 H 1.011954 0.426295 1.167871 0.054 Uiso 1 1 calc R U . . .
C6 C 0.7952(8) 0.4509(6) 0.6328(5) 0.044(2) Uani 1 1 d . . . . .
C16 C 1.2682(8) 0.3736(6) 1.1248(5) 0.045(2) Uani 1 1 d . . . . .
H16 H 1.354688 0.365641 1.151940 0.054 Uiso 1 1 calc R U . . .
C15 C 1.1919(8) 0.4015(6) 1.1739(5) 0.046(2) Uani 1 1 d . . . . .
H15 H 1.227405 0.414769 1.233228 0.055 Uiso 1 1 calc R U . . .
C9 C 0.6035(7) 0.3215(6) 0.7513(6) 0.052(2) Uani 1 1 d . . . . .
H9A H 0.530740 0.362964 0.732455 0.062 Uiso 1 1 calc R U . . .
H9B H 0.583288 0.265107 0.715860 0.062 Uiso 1 1 calc R U . . .
C12 C 0.8725(7) 0.3962(6) 1.0080(5) 0.0407(19) Uani 1 1 d . . . . .
H12 H 0.827195 0.406790 1.046869 0.049 Uiso 1 1 calc R U . . .
O5 O 1.3016(8) 0.2404(6) 0.6270(5) 0.086(2) Uani 1 1 d . . . . .
C11 C 0.6687(7) 0.3760(7) 0.9058(6) 0.056(2) Uani 1 1 d . . . . .
H11A H 0.627345 0.433446 0.879217 0.067 Uiso 1 1 calc R U . . .
H11B H 0.646888 0.364565 0.958832 0.067 Uiso 1 1 calc R U . . .
C19 C 1.4044(7) 0.2836(7) 1.0226(6) 0.055(2) Uani 1 1 d . . . . .
H19A H 1.462607 0.329111 1.057193 0.083 Uiso 1 1 calc R U . . .
H19B H 1.436968 0.259043 0.978311 0.083 Uiso 1 1 calc R U . . .
H19C H 1.394204 0.233366 1.059607 0.083 Uiso 1 1 calc R U . . .
O8 O 1.0386(11) 0.0549(7) 0.8415(7) 0.145(5) Uani 1 1 d . . . . .
C7 C 0.6987(8) 0.3958(6) 0.6558(6) 0.048(2) Uani 1 1 d . . . . .
C10 C 0.6251(8) 0.2959(7) 0.8438(7) 0.057(2) Uani 1 1 d . . . . .
H10A H 0.687931 0.246287 0.859798 0.069 Uiso 1 1 calc R U . . .
H10B H 0.546917 0.271270 0.849847 0.069 Uiso 1 1 calc R U . . .
C2 C 1.0099(10) 0.4982(7) 0.6529(6) 0.058(2) Uani 1 1 d . . . . .
H2 H 1.096051 0.493793 0.683150 0.070 Uiso 1 1 calc R U . . .
C8 C 0.5785(8) 0.3754(8) 0.5826(6) 0.071(3) Uani 1 1 d . . . . .
H8A H 0.561294 0.309193 0.580763 0.107 Uiso 1 1 calc R U . . .
H8B H 0.588108 0.394801 0.527851 0.107 Uiso 1 1 calc R U . . .
H8C H 0.509518 0.409038 0.592561 0.107 Uiso 1 1 calc R U . . .
C3 C 0.9699(13) 0.5581(8) 0.5829(7) 0.075(3) Uani 1 1 d . . . . .
H3 H 1.028865 0.593864 0.566619 0.091 Uiso 1 1 calc R U . . .
C5 C 0.7594(11) 0.5128(8) 0.5608(6) 0.069(3) Uani 1 1 d . . . . .
H5 H 0.674158 0.517456 0.528354 0.083 Uiso 1 1 calc R U . . .
C4 C 0.8447(15) 0.5659(8) 0.5369(7) 0.086(4) Uani 1 1 d . . . . .
H4 H 0.817822 0.606981 0.489708 0.103 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Tb1 O2 2.308(5) . ?
Tb1 O1 2.340(5) . ?
Tb1 O6 2.383(6) . ?
Tb1 O7 2.416(6) . ?
Tb1 O12 2.431(6) . ?
Tb1 O10 2.435(6) . ?
Tb1 O9 2.443(7) . ?
Tb1 O4 2.447(6) . ?
Tb1 O3 2.510(5) . ?
Tb1 N3 2.841(7) . ?
Tb1 N4 2.851(9) . ?
Tb1 N5 2.863(8) . ?
Cu1 O1 1.920(5) . ?
Cu1 N2 1.932(6) . ?
Cu1 O2 1.934(5) . ?
Cu1 N1 1.966(6) . ?
O1 C1 1.339(9) . ?
O3 C17 1.393(9) . ?
O3 C19 1.448(9) . ?
O2 C18 1.317(9) . ?
O12 N5 1.258(9) . ?
O10 N5 1.264(9) . ?
O6 N3 1.259(10) . ?
O4 N3 1.268(10) . ?
O9 N4 1.251(10) . ?
O7 N4 1.253(10) . ?
N2 C12 1.278(10) . ?
N2 C11 1.477(10) . ?
N1 C7 1.292(11) . ?
N1 C9 1.486(10) . ?
C18 C13 1.400(11) . ?
C18 C17 1.421(10) . ?
N3 O5 1.195(9) . ?
C17 C16 1.358(11) . ?
C13 C14 1.391(11) . ?
C13 C12 1.444(10) . ?
C1 C2 1.374(12) . ?
C1 C6 1.416(11) . ?
N4 O8 1.198(11) . ?
N5 O11 1.206(10) . ?
C14 C15 1.375(12) . ?
C6 C5 1.410(13) . ?
C6 C7 1.466(13) . ?
C16 C15 1.386(12) . ?
C9 C10 1.475(13) . ?
C11 C10 1.492(13) . ?
C7 C8 1.506(11) . ?
C2 C3 1.371(13) . ?
C3 C4 1.360(16) . ?
C5 C4 1.359(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 Tb1 O1 65.20(17) . . ?
O2 Tb1 O6 144.1(2) . . ?
O1 Tb1 O6 79.2(2) . . ?
O2 Tb1 O7 83.1(2) . . ?
O1 Tb1 O7 76.0(2) . . ?
O6 Tb1 O7 84.0(2) . . ?
O2 Tb1 O12 122.8(2) . . ?
O1 Tb1 O12 122.0(2) . . ?
O6 Tb1 O12 79.4(2) . . ?
O7 Tb1 O12 152.1(2) . . ?
O2 Tb1 O10 79.7(2) . . ?
O1 Tb1 O10 79.5(2) . . ?
O6 Tb1 O10 98.9(2) . . ?
O7 Tb1 O10 154.3(2) . . ?
O12 Tb1 O10 51.83(19) . . ?
O2 Tb1 O9 82.4(2) . . ?
O1 Tb1 O9 121.4(2) . . ?
O6 Tb1 O9 114.5(2) . . ?
O7 Tb1 O9 51.8(2) . . ?
O12 Tb1 O9 116.6(2) . . ?
O10 Tb1 O9 142.6(2) . . ?
O2 Tb1 O4 155.9(2) . . ?
O1 Tb1 O4 128.6(2) . . ?
O6 Tb1 O4 52.4(2) . . ?
O7 Tb1 O4 82.2(2) . . ?
O12 Tb1 O4 69.9(2) . . ?
O10 Tb1 O4 119.8(2) . . ?
O9 Tb1 O4 73.5(3) . . ?
O2 Tb1 O3 64.76(16) . . ?
O1 Tb1 O3 126.25(17) . . ?
O6 Tb1 O3 149.7(2) . . ?
O7 Tb1 O3 115.7(2) . . ?
O12 Tb1 O3 72.9(2) . . ?
O10 Tb1 O3 73.6(2) . . ?
O9 Tb1 O3 69.1(2) . . ?
O4 Tb1 O3 105.1(2) . . ?
O2 Tb1 N3 165.3(2) . . ?
O1 Tb1 N3 104.5(2) . . ?
O6 Tb1 N3 26.1(2) . . ?
O7 Tb1 N3 84.1(2) . . ?
O12 Tb1 N3 71.2(2) . . ?
O10 Tb1 N3 109.6(2) . . ?
O9 Tb1 N3 95.4(3) . . ?
O4 Tb1 N3 26.4(2) . . ?
O3 Tb1 N3 128.1(2) . . ?
O2 Tb1 N4 81.7(2) . . ?
O1 Tb1 N4 98.8(2) . . ?
O6 Tb1 N4 100.1(3) . . ?
O7 Tb1 N4 25.9(2) . . ?
O12 Tb1 N4 137.9(3) . . ?
O10 Tb1 N4 160.2(2) . . ?
O9 Tb1 N4 25.9(2) . . ?
O4 Tb1 N4 76.8(3) . . ?
O3 Tb1 N4 92.3(2) . . ?
N3 Tb1 N4 90.0(3) . . ?
O2 Tb1 N5 101.0(2) . . ?
O1 Tb1 N5 102.0(2) . . ?
O6 Tb1 N5 90.4(2) . . ?
O7 Tb1 N5 174.3(2) . . ?
O12 Tb1 N5 25.88(19) . . ?
O10 Tb1 N5 26.02(19) . . ?
O9 Tb1 N5 132.4(2) . . ?
O4 Tb1 N5 95.2(2) . . ?
O3 Tb1 N5 69.9(2) . . ?
N3 Tb1 N5 91.3(2) . . ?
N4 Tb1 N5 158.2(3) . . ?
O1 Cu1 N2 167.8(3) . . ?
O1 Cu1 O2 81.1(2) . . ?
N2 Cu1 O2 91.0(2) . . ?
O1 Cu1 N1 91.7(3) . . ?
N2 Cu1 N1 98.3(3) . . ?
O2 Cu1 N1 162.7(3) . . ?
O1 Cu1 Tb1 42.00(15) . . ?
N2 Cu1 Tb1 131.89(18) . . ?
O2 Cu1 Tb1 41.14(15) . . ?
N1 Cu1 Tb1 126.6(2) . . ?
C1 O1 Cu1 119.2(5) . . ?
C1 O1 Tb1 134.2(5) . . ?
Cu1 O1 Tb1 104.7(2) . . ?
C17 O3 C19 116.0(6) . . ?
C17 O3 Tb1 118.0(4) . . ?
C19 O3 Tb1 124.1(5) . . ?
C18 O2 Cu1 127.6(5) . . ?
C18 O2 Tb1 125.7(4) . . ?
Cu1 O2 Tb1 105.4(2) . . ?
N5 O12 Tb1 96.6(4) . . ?
N5 O10 Tb1 96.3(5) . . ?
N3 O6 Tb1 97.7(5) . . ?
N3 O4 Tb1 94.4(5) . . ?
N4 O9 Tb1 95.5(5) . . ?
N4 O7 Tb1 96.8(5) . . ?
C12 N2 C11 117.8(7) . . ?
C12 N2 Cu1 125.8(5) . . ?
C11 N2 Cu1 116.4(5) . . ?
C7 N1 C9 117.0(7) . . ?
C7 N1 Cu1 123.4(6) . . ?
C9 N1 Cu1 119.4(6) . . ?
O2 C18 C13 123.9(7) . . ?
O2 C18 C17 118.2(7) . . ?
C13 C18 C17 117.9(7) . . ?
O5 N3 O6 122.8(9) . . ?
O5 N3 O4 122.2(9) . . ?
O6 N3 O4 115.0(7) . . ?
O5 N3 Tb1 172.7(7) . . ?
O6 N3 Tb1 56.2(4) . . ?
O4 N3 Tb1 59.2(4) . . ?
C16 C17 O3 126.1(7) . . ?
C16 C17 C18 121.1(8) . . ?
O3 C17 C18 112.7(6) . . ?
C14 C13 C18 119.7(7) . . ?
C14 C13 C12 118.9(7) . . ?
C18 C13 C12 121.2(7) . . ?
O1 C1 C2 120.0(8) . . ?
O1 C1 C6 121.0(8) . . ?
C2 C1 C6 119.0(8) . . ?
O8 N4 O9 123.7(10) . . ?
O8 N4 O7 120.4(9) . . ?
O9 N4 O7 115.8(8) . . ?
O8 N4 Tb1 177.7(8) . . ?
O9 N4 Tb1 58.5(5) . . ?
O7 N4 Tb1 57.3(4) . . ?
O11 N5 O12 123.1(8) . . ?
O11 N5 O10 121.9(8) . . ?
O12 N5 O10 115.0(7) . . ?
O11 N5 Tb1 175.8(8) . . ?
O12 N5 Tb1 57.5(4) . . ?
O10 N5 Tb1 57.7(4) . . ?
C15 C14 C13 121.1(8) . . ?
C5 C6 C1 117.0(9) . . ?
C5 C6 C7 120.0(8) . . ?
C1 C6 C7 123.0(7) . . ?
C17 C16 C15 120.4(8) . . ?
C14 C15 C16 119.7(7) . . ?
C10 C9 N1 114.0(7) . . ?
N2 C12 C13 127.1(7) . . ?
N2 C11 C10 109.0(7) . . ?
N1 C7 C6 122.2(7) . . ?
N1 C7 C8 121.2(9) . . ?
C6 C7 C8 116.6(8) . . ?
C9 C10 C11 113.6(8) . . ?
C3 C2 C1 121.6(10) . . ?
C4 C3 C2 120.7(11) . . ?
C4 C5 C6 122.5(10) . . ?
C5 C4 C3 119.2(10) . . ?

_refine_diff_density_max         1.898
_refine_diff_density_min         -0.649
_refine_diff_density_rms         0.147

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

data_2
_database_code_depnum_ccdc_archive 'CCDC 1851679'
_audit_update_record             
;
2018-10-08 deposited with the CCDC.
2018-11-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H20 Cu Dy N5 O12'
_chemical_formula_sum            'C19 H20 Cu Dy N5 O12'
_chemical_formula_weight         736.45


loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Dy Dy -0.1892 4.4098 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.168(5)
_cell_length_b                   14.259(5)
_cell_length_c                   16.198(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 108.516(5)
_cell_angle_gamma                90.00
_cell_volume                     2445.9(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4364
_cell_measurement_theta_min      1.95
_cell_measurement_theta_max      25.11

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.000
_exptl_crystal_F_000             1440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    3.974
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   EMPIRICAL
_exptl_absorpt_correction_T_min  0.826
_exptl_absorpt_correction_T_max  0.924
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26354
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_av_R_equivalents  0.0433
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.949
_diffrn_reflns_theta_max         25.112
_diffrn_reflns_theta_full        25.112
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             4366
_reflns_number_gt                3795
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0418P)²+3.2920P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4330
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0291
_refine_ls_wR_factor_ref         0.0793
_refine_ls_wR_factor_gt          0.0743
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Dy1 Dy 0.33763(2) 0.31994(2) 0.67899(2) 0.03576(9) Uani 1 1 d . . . . .
Cu1 Cu 0.62608(5) 0.37895(4) 0.66925(3) 0.03733(14) Uani 1 1 d . . . . .
O3 O 0.2173(3) 0.3286(2) 0.5188(2) 0.0463(8) Uani 1 1 d . . . . .
O1 O 0.5318(3) 0.3889(2) 0.75016(18) 0.0416(7) Uani 1 1 d . . . . .
O2 O 0.4584(3) 0.3526(2) 0.59072(17) 0.0405(7) Uani 1 1 d . . . . .
O12 O 0.1366(3) 0.3960(3) 0.6621(3) 0.0686(11) Uani 1 1 d . . . . .
O10 O 0.2837(3) 0.4837(2) 0.6469(3) 0.0607(9) Uani 1 1 d . . . . .
O4 O 0.2078(4) 0.2209(3) 0.7392(3) 0.0719(11) Uani 1 1 d . . . . .
O7 O 0.4836(4) 0.1914(3) 0.7225(3) 0.0779(13) Uani 1 1 d . . . . .
O6 O 0.3379(4) 0.3147(3) 0.8262(3) 0.0745(12) Uani 1 1 d . . . . .
N2 N 0.6924(3) 0.3859(3) 0.5720(2) 0.0414(8) Uani 1 1 d . . . . .
O9 O 0.3260(4) 0.1663(3) 0.6100(3) 0.0765(13) Uani 1 1 d . . . . .
C18 C 0.4144(4) 0.3677(3) 0.5052(3) 0.0340(9) Uani 1 1 d . . . . .
N1 N 0.7878(3) 0.3703(3) 0.7648(3) 0.0455(9) Uani 1 1 d . . . . .
C13 C 0.4918(4) 0.3922(3) 0.4554(3) 0.0360(9) Uani 1 1 d . . . . .
C17 C 0.2839(4) 0.3561(3) 0.4631(3) 0.0386(9) Uani 1 1 d . . . . .
C1 C 0.5754(5) 0.4457(3) 0.8203(3) 0.0436(10) Uani 1 1 d . . . . .
N5 N 0.1702(4) 0.4769(3) 0.6440(3) 0.0641(12) Uani 1 1 d . . . . .
C12 C 0.6277(4) 0.3947(3) 0.4917(3) 0.0398(10) Uani 1 1 d . . . . .
H12 H 0.672561 0.403533 0.452770 0.048 Uiso 1 1 calc R U . . .
C6 C 0.7045(5) 0.4519(3) 0.8667(3) 0.0506(12) Uani 1 1 d . . . . .
N4 N 0.4262(6) 0.1362(4) 0.6627(3) 0.0829(17) Uani 1 1 d . . . . .
O11 O 0.0970(5) 0.5416(4) 0.6236(5) 0.118(2) Uani 1 1 d . . . . .
C15 C 0.3082(5) 0.3977(4) 0.3266(3) 0.0530(12) Uani 1 1 d . . . . .
H15 H 0.272784 0.409174 0.267264 0.064 Uiso 1 1 calc R U . . .
C14 C 0.4366(5) 0.4069(3) 0.3655(3) 0.0461(11) Uani 1 1 d . . . . .
H14 H 0.487306 0.423038 0.331894 0.055 Uiso 1 1 calc R U . . .
N3 N 0.2482(5) 0.2575(3) 0.8152(3) 0.0633(12) Uani 1 1 d . . . . .
O5 O 0.2028(5) 0.2400(4) 0.8712(3) 0.1052(17) Uani 1 1 d . . . . .
C16 C 0.2312(5) 0.3714(3) 0.3751(3) 0.0474(11) Uani 1 1 d . . . . .
H16 H 0.144752 0.364123 0.348346 0.057 Uiso 1 1 calc R U . . .
C7 C 0.8021(5) 0.3981(4) 0.8432(3) 0.0511(12) Uani 1 1 d . . . . .
C9 C 0.8985(5) 0.3240(4) 0.7492(4) 0.0591(14) Uani 1 1 d . . . . .
H9A H 0.970220 0.366227 0.767254 0.071 Uiso 1 1 calc R U . . .
H9B H 0.920170 0.268169 0.785127 0.071 Uiso 1 1 calc R U . . .
C11 C 0.8312(5) 0.3774(4) 0.5930(4) 0.0578(13) Uani 1 1 d . . . . .
H11A H 0.871964 0.435271 0.618654 0.069 Uiso 1 1 calc R U . . .
H11B H 0.852539 0.365233 0.540418 0.069 Uiso 1 1 calc R U . . .
C19 C 0.0972(5) 0.2836(4) 0.4789(4) 0.0603(14) Uani 1 1 d . . . . .
H19A H 0.039640 0.327505 0.441755 0.090 Uiso 1 1 calc R U . . .
H19B H 0.063699 0.262290 0.523336 0.090 Uiso 1 1 calc R U . . .
H19C H 0.108267 0.231013 0.445005 0.090 Uiso 1 1 calc R U . . .
C10 C 0.8760(5) 0.2971(4) 0.6567(4) 0.0611(14) Uani 1 1 d . . . . .
H10A H 0.813357 0.247481 0.641422 0.073 Uiso 1 1 calc R U . . .
H10B H 0.953725 0.272182 0.650837 0.073 Uiso 1 1 calc R U . . .
C3 C 0.5308(8) 0.5587(5) 0.9180(4) 0.082(2) Uani 1 1 d . . . . .
H3 H 0.472706 0.593736 0.935263 0.098 Uiso 1 1 calc R U . . .
C2 C 0.4895(6) 0.4990(4) 0.8464(3) 0.0623(14) Uani 1 1 d . . . . .
H2 H 0.403705 0.494759 0.815802 0.075 Uiso 1 1 calc R U . . .
C5 C 0.7400(7) 0.5135(5) 0.9386(4) 0.0786(19) Uani 1 1 d . . . . .
H5 H 0.825142 0.518030 0.970785 0.094 Uiso 1 1 calc R U . . .
C8 C 0.9230(6) 0.3752(5) 0.9169(4) 0.086(2) Uani 1 1 d . . . . .
H8A H 0.946059 0.311047 0.912134 0.129 Uiso 1 1 calc R U . . .
H8B H 0.909334 0.384590 0.971909 0.129 Uiso 1 1 calc R U . . .
H8C H 0.989799 0.415616 0.913020 0.129 Uiso 1 1 calc R U . . .
O8 O 0.4677(7) 0.0594(4) 0.6562(4) 0.151(3) Uani 1 1 d . . . . .
C4 C 0.6571(9) 0.5657(5) 0.9628(4) 0.093(2) Uani 1 1 d . . . . .
H4 H 0.685115 0.606501 1.009847 0.112 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Dy1 O2 2.303(3) . ?
Dy1 O1 2.326(3) . ?
Dy1 O6 2.385(4) . ?
Dy1 O7 2.405(4) . ?
Dy1 O10 2.427(4) . ?
Dy1 O12 2.430(4) . ?
Dy1 O4 2.439(4) . ?
Dy1 O9 2.443(4) . ?
Dy1 O3 2.518(3) . ?
Dy1 N3 2.838(4) . ?
Dy1 N4 2.842(5) . ?
Dy1 N5 2.855(5) . ?
Cu1 O1 1.930(3) . ?
Cu1 O2 1.937(3) . ?
Cu1 N2 1.945(4) . ?
Cu1 N1 1.974(4) . ?
O3 C17 1.395(5) . ?
O3 C19 1.441(6) . ?
O1 C1 1.353(5) . ?
O2 C18 1.331(5) . ?
O12 N5 1.276(6) . ?
O10 N5 1.257(5) . ?
O4 N3 1.279(6) . ?
O7 N4 1.255(7) . ?
O6 N3 1.260(6) . ?
N2 C12 1.278(6) . ?
N2 C11 1.482(6) . ?
O9 N4 1.248(6) . ?
C18 C13 1.401(6) . ?
C18 C17 1.410(6) . ?
N1 C7 1.292(6) . ?
N1 C9 1.492(7) . ?
C13 C14 1.405(6) . ?
C13 C12 1.444(6) . ?
C17 C16 1.376(6) . ?
C1 C2 1.391(7) . ?
C1 C6 1.402(7) . ?
N5 O11 1.207(6) . ?
C6 C5 1.412(8) . ?
C6 C7 1.477(8) . ?
N4 O8 1.207(7) . ?
C15 C14 1.377(7) . ?
C15 C16 1.389(7) . ?
N3 O5 1.198(6) . ?
C7 C8 1.527(7) . ?
C9 C10 1.489(8) . ?
C11 C10 1.516(8) . ?
C3 C4 1.369(10) . ?
C3 C2 1.394(8) . ?
C5 C4 1.341(10) . ?

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 Dy1 O1 65.45(10) . . ?
O2 Dy1 O6 144.28(13) . . ?
O1 Dy1 O6 79.20(13) . . ?
O2 Dy1 O7 81.97(15) . . ?
O1 Dy1 O7 74.84(13) . . ?
O6 Dy1 O7 84.11(16) . . ?
O2 Dy1 O10 80.00(12) . . ?
O1 Dy1 O10 80.09(12) . . ?
O6 Dy1 O10 99.55(15) . . ?
O7 Dy1 O10 153.53(14) . . ?
O2 Dy1 O12 122.82(12) . . ?
O1 Dy1 O12 123.34(13) . . ?
O6 Dy1 O12 80.46(15) . . ?
O7 Dy1 O12 152.80(15) . . ?
O10 Dy1 O12 52.31(12) . . ?
O2 Dy1 O4 154.88(14) . . ?
O1 Dy1 O4 128.74(13) . . ?
O6 Dy1 O4 52.69(15) . . ?
O7 Dy1 O4 82.84(16) . . ?
O10 Dy1 O4 120.28(14) . . ?
O12 Dy1 O4 69.99(14) . . ?
O2 Dy1 O9 81.62(15) . . ?
O1 Dy1 O9 120.76(14) . . ?
O6 Dy1 O9 114.34(16) . . ?
O7 Dy1 O9 51.95(14) . . ?
O10 Dy1 O9 142.30(14) . . ?
O12 Dy1 O9 115.84(15) . . ?
O4 Dy1 O9 73.26(17) . . ?
O2 Dy1 O3 64.94(10) . . ?
O1 Dy1 O3 126.77(10) . . ?
O6 Dy1 O3 149.64(13) . . ?
O7 Dy1 O3 115.45(13) . . ?
O10 Dy1 O3 73.58(12) . . ?
O12 Dy1 O3 71.97(13) . . ?
O4 Dy1 O3 104.48(13) . . ?
O9 Dy1 O3 68.84(12) . . ?
O2 Dy1 N3 164.99(12) . . ?
O1 Dy1 N3 104.49(13) . . ?
O6 Dy1 N3 26.11(14) . . ?
O7 Dy1 N3 84.61(16) . . ?
O10 Dy1 N3 110.12(13) . . ?
O12 Dy1 N3 71.75(14) . . ?
O4 Dy1 N3 26.70(13) . . ?
O9 Dy1 N3 95.36(16) . . ?
O3 Dy1 N3 127.73(13) . . ?
O2 Dy1 N4 80.75(16) . . ?
O1 Dy1 N4 97.97(15) . . ?
O6 Dy1 N4 100.03(16) . . ?
O7 Dy1 N4 26.01(14) . . ?
O10 Dy1 N4 159.59(16) . . ?
O12 Dy1 N4 137.53(17) . . ?
O4 Dy1 N4 76.85(17) . . ?
O9 Dy1 N4 25.94(14) . . ?
O3 Dy1 N4 92.11(13) . . ?
N3 Dy1 N4 90.11(16) . . ?
O2 Dy1 N5 101.17(13) . . ?
O1 Dy1 N5 102.44(13) . . ?
O6 Dy1 N5 90.91(15) . . ?
O7 Dy1 N5 174.68(15) . . ?
O10 Dy1 N5 25.95(12) . . ?
O12 Dy1 N5 26.39(12) . . ?
O4 Dy1 N5 95.63(15) . . ?
O9 Dy1 N5 132.50(14) . . ?
O3 Dy1 N5 69.86(13) . . ?
N3 Dy1 N5 91.74(14) . . ?
N4 Dy1 N5 158.34(16) . . ?
O1 Cu1 O2 80.68(12) . . ?
O1 Cu1 N2 167.68(14) . . ?
O2 Cu1 N2 90.89(14) . . ?
O1 Cu1 N1 91.90(15) . . ?
O2 Cu1 N1 162.86(15) . . ?
N2 Cu1 N1 98.57(16) . . ?
O1 Cu1 Dy1 41.68(8) . . ?
O2 Cu1 Dy1 41.05(8) . . ?
N2 Cu1 Dy1 131.62(11) . . ?
N1 Cu1 Dy1 126.58(12) . . ?
C17 O3 C19 116.5(4) . . ?
C17 O3 Dy1 117.4(2) . . ?
C19 O3 Dy1 123.8(3) . . ?
C1 O1 Cu1 119.1(3) . . ?
C1 O1 Dy1 134.4(3) . . ?
Cu1 O1 Dy1 104.84(12) . . ?
C18 O2 Cu1 127.7(3) . . ?
C18 O2 Dy1 125.7(2) . . ?
Cu1 O2 Dy1 105.43(12) . . ?
N5 O12 Dy1 95.8(3) . . ?
N5 O10 Dy1 96.4(3) . . ?
N3 O4 Dy1 94.3(3) . . ?
N4 O7 Dy1 96.8(3) . . ?
N3 O6 Dy1 97.4(3) . . ?
C12 N2 C11 117.0(4) . . ?
C12 N2 Cu1 126.3(3) . . ?
C11 N2 Cu1 116.7(3) . . ?
N4 O9 Dy1 95.2(3) . . ?
O2 C18 C13 123.3(4) . . ?
O2 C18 C17 117.9(4) . . ?
C13 C18 C17 118.8(4) . . ?
C7 N1 C9 116.9(4) . . ?
C7 N1 Cu1 123.2(3) . . ?
C9 N1 Cu1 119.8(3) . . ?
C18 C13 C14 119.2(4) . . ?
C18 C13 C12 122.1(4) . . ?
C14 C13 C12 118.5(4) . . ?
C16 C17 O3 125.0(4) . . ?
C16 C17 C18 121.3(4) . . ?
O3 C17 C18 113.7(4) . . ?
O1 C1 C2 118.9(4) . . ?
O1 C1 C6 121.5(4) . . ?
C2 C1 C6 119.6(4) . . ?
O11 N5 O10 122.6(5) . . ?
O11 N5 O12 122.1(5) . . ?
O10 N5 O12 115.4(4) . . ?
O11 N5 Dy1 175.7(5) . . ?
O10 N5 Dy1 57.6(2) . . ?
O12 N5 Dy1 57.8(2) . . ?
N2 C12 C13 126.5(4) . . ?
C1 C6 C5 116.9(5) . . ?
C1 C6 C7 123.2(4) . . ?
C5 C6 C7 119.9(5) . . ?
O8 N4 O9 122.6(6) . . ?
O8 N4 O7 121.3(6) . . ?
O9 N4 O7 116.1(5) . . ?
O8 N4 Dy1 177.9(6) . . ?
O9 N4 Dy1 58.9(3) . . ?
O7 N4 Dy1 57.2(3) . . ?
C14 C15 C16 120.6(4) . . ?
C15 C14 C13 120.7(4) . . ?
O5 N3 O6 122.4(6) . . ?
O5 N3 O4 122.6(5) . . ?
O6 N3 O4 115.0(4) . . ?
O5 N3 Dy1 172.8(4) . . ?
O6 N3 Dy1 56.4(2) . . ?
O4 N3 Dy1 59.0(2) . . ?
C17 C16 C15 119.4(4) . . ?
N1 C7 C6 122.8(4) . . ?
N1 C7 C8 120.4(5) . . ?
C6 C7 C8 116.8(5) . . ?
C10 C9 N1 113.6(4) . . ?
N2 C11 C10 108.2(4) . . ?
C9 C10 C11 113.8(5) . . ?
C4 C3 C2 120.0(6) . . ?
C1 C2 C3 120.6(6) . . ?
C4 C5 C6 123.2(6) . . ?
C5 C4 C3 119.6(6) . . ?

_refine_diff_density_max         1.386
_refine_diff_density_min         -1.082
_refine_diff_density_rms         0.104

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

data_3
_database_code_depnum_ccdc_archive 'CCDC 1851680'
_audit_update_record             
;
2018-10-08 deposited with the CCDC.
2018-11-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H20 Cu Ho N5 O12'
_chemical_formula_sum            'C19 H20 Cu Ho N5 O12'
_chemical_formula_weight         738.88
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Ho Ho -0.2175 4.6783 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.090(5)
_cell_length_b                   14.296(5)
_cell_length_c                   16.040(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 108.252(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     2415.1(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4269
_cell_measurement_theta_min      1.95
_cell_measurement_theta_max      25.02

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      2.032
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.032
_exptl_crystal_F_000             1444
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    4.207
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   EMPIRICAL
_exptl_absorpt_correction_T_min  0.817
_exptl_absorpt_correction_T_max  0.919
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27205
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.954
_diffrn_reflns_theta_max         25.015
_diffrn_reflns_theta_full        25.015
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4265
_reflns_number_gt                3729
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0272P)²+0.6896P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4247
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0233
_refine_ls_wR_factor_ref         0.0558
_refine_ls_wR_factor_gt          0.0538
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ho1 Ho 0.16400(2) 0.81790(2) 0.32107(2) 0.02914(7) Uani 1 1 d . . . . .
Cu1 Cu -0.12465(4) 0.87667(3) 0.33002(3) 0.03110(11) Uani 1 1 d . . . . .
O1 O -0.0304(2) 0.88587(16) 0.24836(15) 0.0349(6) Uani 1 1 d . . . . .
C9 C -0.3960(4) 0.8208(3) 0.2501(3) 0.0489(11) Uani 1 1 d . . . . .
H9A H -0.415710 0.764780 0.214277 0.059 Uiso 1 1 calc R U . . .
H9B H -0.469133 0.861896 0.231160 0.059 Uiso 1 1 calc R U . . .
O3 O 0.2850(2) 0.82903(17) 0.48149(16) 0.0381(6) Uani 1 1 d . . . . .
O10 O 0.2150(2) 0.98141(18) 0.35177(18) 0.0476(7) Uani 1 1 d . . . . .
O6 O 0.1652(3) 0.8139(2) 0.17334(18) 0.0544(8) Uani 1 1 d . . . . .
O2 O 0.0421(2) 0.85092(17) 0.40875(14) 0.0333(5) Uani 1 1 d . . . . .
O12 O 0.3629(2) 0.89560(19) 0.33491(19) 0.0533(7) Uani 1 1 d . . . . .
O7 O 0.0220(3) 0.68880(19) 0.27500(19) 0.0582(8) Uani 1 1 d . . . . .
O9 O 0.1783(3) 0.66569(19) 0.39136(19) 0.0575(8) Uani 1 1 d . . . . .
O4 O 0.2952(3) 0.7199(2) 0.2609(2) 0.0532(7) Uani 1 1 d . . . . .
N2 N -0.1921(3) 0.88485(19) 0.42679(19) 0.0335(7) Uani 1 1 d . . . . .
N1 N -0.2860(3) 0.8683(2) 0.2343(2) 0.0362(7) Uani 1 1 d . . . . .
C18 C 0.0869(3) 0.8674(2) 0.4946(2) 0.0277(7) Uani 1 1 d . . . . .
C1 C -0.0736(4) 0.9441(2) 0.1789(2) 0.0356(8) Uani 1 1 d . . . . .
N3 N 0.2567(3) 0.7566(2) 0.1855(2) 0.0507(9) Uani 1 1 d . . . . .
C13 C 0.0097(3) 0.8936(2) 0.5446(2) 0.0293(7) Uani 1 1 d . . . . .
N4 N 0.0791(4) 0.6339(3) 0.3361(3) 0.0647(11) Uani 1 1 d . . . . .
C11 C -0.3313(3) 0.8756(3) 0.4059(3) 0.0487(10) Uani 1 1 d . . . . .
H11A H -0.372900 0.932687 0.378948 0.058 Uiso 1 1 calc R U . . .
H11B H -0.352840 0.864560 0.459209 0.058 Uiso 1 1 calc R U . . .
C6 C -0.2026(4) 0.9504(3) 0.1329(2) 0.0409(9) Uani 1 1 d . . . . .
C17 C 0.2176(3) 0.8569(2) 0.5366(2) 0.0303(8) Uani 1 1 d . . . . .
C12 C -0.1270(3) 0.8958(2) 0.5076(2) 0.0326(8) Uani 1 1 d . . . . .
H12 H -0.172509 0.906271 0.546539 0.039 Uiso 1 1 calc R U . . .
C16 C 0.2702(4) 0.8738(2) 0.6252(2) 0.0387(9) Uani 1 1 d . . . . .
H16 H 0.357171 0.867034 0.652096 0.046 Uiso 1 1 calc R U . . .
O5 O 0.3022(4) 0.7397(2) 0.1284(2) 0.0826(11) Uani 1 1 d . . . . .
C15 C 0.1935(4) 0.9008(3) 0.6739(2) 0.0445(10) Uani 1 1 d . . . . .
H15 H 0.229175 0.913311 0.733477 0.053 Uiso 1 1 calc R U . . .
C2 C 0.0131(4) 0.9983(3) 0.1532(3) 0.0488(10) Uani 1 1 d . . . . .
H2 H 0.099251 0.993572 0.183820 0.059 Uiso 1 1 calc R U . . .
O11 O 0.4025(3) 1.0401(2) 0.3750(3) 0.0946(13) Uani 1 1 d . . . . .
N5 N 0.3294(3) 0.9754(2) 0.3547(2) 0.0504(9) Uani 1 1 d . . . . .
C19 C 0.4057(3) 0.7842(3) 0.5217(3) 0.0500(10) Uani 1 1 d . . . . .
H19A H 0.394629 0.732483 0.556756 0.075 Uiso 1 1 calc R U . . .
H19B H 0.463874 0.828365 0.558256 0.075 Uiso 1 1 calc R U . . .
H19C H 0.438979 0.761944 0.476835 0.075 Uiso 1 1 calc R U . . .
C14 C 0.0645(4) 0.9094(2) 0.6351(2) 0.0376(9) Uani 1 1 d . . . . .
H14 H 0.013232 0.925848 0.668871 0.045 Uiso 1 1 calc R U . . .
C10 C -0.3746(4) 0.7944(3) 0.3436(3) 0.0510(11) Uani 1 1 d . . . . .
H10A H -0.311154 0.745314 0.359783 0.061 Uiso 1 1 calc R U . . .
H10B H -0.452905 0.769603 0.349517 0.061 Uiso 1 1 calc R U . . .
C8 C -0.4215(4) 0.8747(3) 0.0825(3) 0.0627(13) Uani 1 1 d . . . . .
H8A H -0.489198 0.912805 0.089116 0.094 Uiso 1 1 calc R U . . .
H8B H -0.442688 0.809872 0.084940 0.094 Uiso 1 1 calc R U . . .
H8C H -0.409493 0.887788 0.026902 0.094 Uiso 1 1 calc R U . . .
C4 C -0.1526(6) 1.0667(3) 0.0378(3) 0.0716(15) Uani 1 1 d . . . . .
H4 H -0.179603 1.108192 -0.008999 0.086 Uiso 1 1 calc R U . . .
C7 C -0.3004(3) 0.8962(3) 0.1557(2) 0.0400(9) Uani 1 1 d . . . . .
O8 O 0.0405(4) 0.5565(3) 0.3416(3) 0.1219(18) Uani 1 1 d . . . . .
C3 C -0.0270(5) 1.0587(3) 0.0832(3) 0.0645(13) Uani 1 1 d . . . . .
H3 H 0.032158 1.094287 0.066864 0.077 Uiso 1 1 calc R U . . .
C5 C -0.2383(5) 1.0137(3) 0.0612(3) 0.0631(13) Uani 1 1 d . . . . .
H5 H -0.323781 1.019013 0.028916 0.076 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ho1 O2 2.285(2) . ?
Ho1 O1 2.319(2) . ?
Ho1 O6 2.374(3) . ?
Ho1 O7 2.388(3) . ?
Ho1 O12 2.417(3) . ?
Ho1 O10 2.419(3) . ?
Ho1 O4 2.427(3) . ?
Ho1 O9 2.433(3) . ?
Ho1 O3 2.507(2) . ?
Ho1 N3 2.820(3) . ?
Ho1 N4 2.829(4) . ?
Ho1 N5 2.847(3) . ?
Cu1 O1 1.920(2) . ?
Cu1 O2 1.920(2) . ?
Cu1 N2 1.926(3) . ?
Cu1 N1 1.963(3) . ?
O1 C1 1.352(4) . ?
C9 N1 1.485(5) . ?
C9 C10 1.492(6) . ?
O3 C17 1.383(4) . ?
O3 C19 1.441(4) . ?
O10 N5 1.257(4) . ?
O6 N3 1.270(4) . ?
O2 C18 1.331(4) . ?
O12 N5 1.270(4) . ?
O7 N4 1.260(4) . ?
O9 N4 1.262(4) . ?
O4 N3 1.264(4) . ?
N2 C12 1.280(4) . ?
N2 C11 1.479(4) . ?
N1 C7 1.284(5) . ?
C18 C13 1.395(5) . ?
C18 C17 1.401(5) . ?
C1 C6 1.393(5) . ?
C1 C2 1.394(5) . ?
N3 O5 1.201(4) . ?
C13 C14 1.405(5) . ?
C13 C12 1.446(5) . ?
N4 O8 1.199(4) . ?
C11 C10 1.509(6) . ?
C6 C5 1.418(6) . ?
C6 C7 1.469(5) . ?
C17 C16 1.379(5) . ?
C16 C15 1.378(5) . ?
C15 C14 1.375(5) . ?
C2 C3 1.375(6) . ?
O11 N5 1.206(4) . ?
C8 C7 1.514(5) . ?
C4 C5 1.357(7) . ?
C4 C3 1.360(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
O2 Ho1 O1 65.60(8) . . ?
O2 Ho1 O6 143.95(9) . . ?
O1 Ho1 O6 78.63(9) . . ?
O2 Ho1 O7 83.69(10) . . ?
O1 Ho1 O7 75.48(9) . . ?
O6 Ho1 O7 83.20(11) . . ?
O2 Ho1 O12 123.20(9) . . ?
O1 Ho1 O12 122.11(10) . . ?
O6 Ho1 O12 79.21(10) . . ?
O7 Ho1 O12 151.39(10) . . ?
O2 Ho1 O10 79.69(9) . . ?
O1 Ho1 O10 79.56(9) . . ?
O6 Ho1 O10 98.77(10) . . ?
O7 Ho1 O10 154.07(10) . . ?
O12 Ho1 O10 52.31(9) . . ?
O2 Ho1 O4 155.25(10) . . ?
O1 Ho1 O4 128.34(9) . . ?
O6 Ho1 O4 52.97(10) . . ?
O7 Ho1 O4 81.38(11) . . ?
O12 Ho1 O4 70.02(10) . . ?
O10 Ho1 O4 120.49(10) . . ?
O2 Ho1 O9 82.23(10) . . ?
O1 Ho1 O9 121.56(10) . . ?
O6 Ho1 O9 114.89(10) . . ?
O7 Ho1 O9 52.64(10) . . ?
O12 Ho1 O9 116.31(10) . . ?
O10 Ho1 O9 142.44(10) . . ?
O4 Ho1 O9 73.01(11) . . ?
O2 Ho1 O3 65.47(8) . . ?
O1 Ho1 O3 127.17(8) . . ?
O6 Ho1 O3 149.03(10) . . ?
O7 Ho1 O3 117.11(9) . . ?
O12 Ho1 O3 72.35(9) . . ?
O10 Ho1 O3 73.37(9) . . ?
O4 Ho1 O3 104.48(9) . . ?
O9 Ho1 O3 69.20(9) . . ?
O2 Ho1 N3 165.40(9) . . ?
O1 Ho1 N3 104.36(10) . . ?
O6 Ho1 N3 26.57(10) . . ?
O7 Ho1 N3 83.43(11) . . ?
O12 Ho1 N3 70.79(10) . . ?
O10 Ho1 N3 109.78(10) . . ?
O4 Ho1 N3 26.54(9) . . ?
O9 Ho1 N3 95.34(11) . . ?
O3 Ho1 N3 127.17(10) . . ?
O2 Ho1 N4 82.12(11) . . ?
O1 Ho1 N4 98.67(11) . . ?
O6 Ho1 N4 99.69(11) . . ?
O7 Ho1 N4 26.24(10) . . ?
O12 Ho1 N4 137.54(11) . . ?
O10 Ho1 N4 160.72(11) . . ?
O4 Ho1 N4 75.76(11) . . ?
O9 Ho1 N4 26.40(10) . . ?
O3 Ho1 N4 93.28(10) . . ?
N3 Ho1 N4 89.32(11) . . ?
O2 Ho1 N5 100.98(10) . . ?
O1 Ho1 N5 101.89(10) . . ?
O6 Ho1 N5 90.20(10) . . ?
O7 Ho1 N5 173.25(10) . . ?
O12 Ho1 N5 26.35(9) . . ?
O10 Ho1 N5 26.03(8) . . ?
O4 Ho1 N5 95.79(10) . . ?
O9 Ho1 N5 132.45(10) . . ?
O3 Ho1 N5 69.48(9) . . ?
N3 Ho1 N5 91.31(10) . . ?
N4 Ho1 N5 158.59(11) . . ?
O1 Cu1 O2 81.01(10) . . ?
O1 Cu1 N2 167.91(11) . . ?
O2 Cu1 N2 91.07(11) . . ?
O1 Cu1 N1 91.63(12) . . ?
O2 Cu1 N1 163.12(11) . . ?
N2 Cu1 N1 98.35(13) . . ?
O1 Cu1 Ho1 42.02(7) . . ?
O2 Cu1 Ho1 40.98(7) . . ?
N2 Cu1 Ho1 131.76(9) . . ?
N1 Cu1 Ho1 126.83(9) . . ?
C1 O1 Cu1 118.4(2) . . ?
C1 O1 Ho1 134.9(2) . . ?
Cu1 O1 Ho1 104.32(10) . . ?
N1 C9 C10 114.0(3) . . ?
C17 O3 C19 117.0(3) . . ?
C17 O3 Ho1 116.84(19) . . ?
C19 O3 Ho1 123.7(2) . . ?
N5 O10 Ho1 96.3(2) . . ?
N3 O6 Ho1 96.7(2) . . ?
C18 O2 Cu1 128.1(2) . . ?
C18 O2 Ho1 124.9(2) . . ?
Cu1 O2 Ho1 105.57(10) . . ?
N5 O12 Ho1 96.0(2) . . ?
N4 O7 Ho1 96.8(2) . . ?
N4 O9 Ho1 94.6(2) . . ?
N3 O4 Ho1 94.4(2) . . ?
C12 N2 C11 117.2(3) . . ?
C12 N2 Cu1 125.8(2) . . ?
C11 N2 Cu1 117.0(2) . . ?
C7 N1 C9 117.0(3) . . ?
C7 N1 Cu1 123.5(3) . . ?
C9 N1 Cu1 119.4(3) . . ?
O2 C18 C13 123.0(3) . . ?
O2 C18 C17 118.3(3) . . ?
C13 C18 C17 118.7(3) . . ?
O1 C1 C6 121.1(3) . . ?
O1 C1 C2 119.1(3) . . ?
C6 C1 C2 119.7(3) . . ?
O5 N3 O4 123.3(4) . . ?
O5 N3 O6 121.3(4) . . ?
O4 N3 O6 115.4(3) . . ?
O5 N3 Ho1 173.0(3) . . ?
O4 N3 Ho1 59.10(18) . . ?
O6 N3 Ho1 56.74(18) . . ?
C18 C13 C14 119.5(3) . . ?
C18 C13 C12 121.6(3) . . ?
C14 C13 C12 118.6(3) . . ?
O8 N4 O7 121.8(4) . . ?
O8 N4 O9 122.2(4) . . ?
O7 N4 O9 115.9(3) . . ?
O8 N4 Ho1 178.6(4) . . ?
O7 N4 Ho1 56.94(19) . . ?
O9 N4 Ho1 58.99(19) . . ?
N2 C11 C10 108.2(3) . . ?
C1 C6 C5 116.8(4) . . ?
C1 C6 C7 123.3(3) . . ?
C5 C6 C7 119.9(4) . . ?
C16 C17 O3 124.8(3) . . ?
C16 C17 C18 121.1(3) . . ?
O3 C17 C18 114.1(3) . . ?
N2 C12 C13 126.8(3) . . ?
C15 C16 C17 119.7(3) . . ?
C14 C15 C16 120.5(3) . . ?
C3 C2 C1 121.0(4) . . ?
O11 N5 O10 122.9(4) . . ?
O11 N5 O12 122.1(4) . . ?
O10 N5 O12 115.0(3) . . ?
O11 N5 Ho1 175.4(3) . . ?
O10 N5 Ho1 57.63(17) . . ?
O12 N5 Ho1 57.61(17) . . ?
C15 C14 C13 120.3(3) . . ?
C9 C10 C11 112.9(3) . . ?
C5 C4 C3 119.6(4) . . ?
N1 C7 C6 122.3(3) . . ?
N1 C7 C8 120.4(4) . . ?
C6 C7 C8 117.3(4) . . ?
C4 C3 C2 120.3(5) . . ?
C4 C5 C6 122.6(4) . . ?

_refine_diff_density_max         0.899
_refine_diff_density_min         -0.428
_refine_diff_density_rms         0.079

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

data_4
_database_code_depnum_ccdc_archive 'CCDC 1851681'
_audit_update_record             
;
2018-10-08 deposited with the CCDC.
2018-11-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/1
_shelx_SHELXL_version_number     2018/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H20 Cu Er N5 O12'
_chemical_formula_sum            'C19 H20 Cu Er N5 O12'
_chemical_formula_weight         741.21

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Er Er -0.2586 4.9576 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.073(5)
_cell_length_b                   14.257(5)
_cell_length_c                   16.022(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 108.285(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     2401.6(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4456
_cell_measurement_theta_min      1.96
_cell_measurement_theta_max      25.46

_exptl_crystal_description       Prismatic
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    2.050
_exptl_crystal_F_000             1448
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.06
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    4.430
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   EMPIRICAL
_exptl_absorpt_correction_T_min  0.767
_exptl_absorpt_correction_T_max  0.876
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16662
_diffrn_reflns_av_unetI/netI     0.0544
_diffrn_reflns_av_R_equivalents  0.0543
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.958
_diffrn_reflns_theta_max         25.463
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4456
_reflns_number_gt                3769
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0679P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4383
_refine_ls_number_parameters     345
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.1081
_refine_ls_wR_factor_gt          0.1026
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Er1 Er 0.16340(2) 0.81858(2) 0.82136(2) 0.03323(12) Uani 1 1 d . . . . .
Cu1 Cu -0.12478(6) 0.87713(4) 0.82990(4) 0.03509(18) Uani 1 1 d . . . . .
O1 O -0.0295(3) 0.8867(2) 0.7492(2) 0.0387(8) Uani 1 1 d . . . . .
O3 O 0.2849(4) 0.8293(2) 0.9810(3) 0.0424(9) Uani 1 1 d . . . . .
O6 O 0.1646(5) 0.8144(3) 0.6746(3) 0.0600(13) Uani 1 1 d . . . . .
O12 O 0.3619(4) 0.8949(3) 0.8349(3) 0.0572(11) Uani 1 1 d . . . . .
O2 O 0.0415(3) 0.8510(3) 0.9087(2) 0.0376(8) Uani 1 1 d . . . . .
O7 O 0.0211(5) 0.6901(3) 0.7752(3) 0.0646(14) Uani 1 1 d . . . . .
O10 O 0.2134(4) 0.9810(3) 0.8519(3) 0.0506(10) Uani 1 1 d . . . . .
C9 C -0.3965(6) 0.8213(4) 0.7495(5) 0.0546(17) Uani 1 1 d . . . . .
H9A H -0.416415 0.765238 0.713437 0.066 Uiso 1 1 calc R U . . .
H9B H -0.469657 0.862636 0.730629 0.066 Uiso 1 1 calc R U . . .
O8 O 0.0368(7) 0.5576(4) 0.8420(4) 0.121(3) Uani 1 1 d . . . . .
O9 O 0.1779(5) 0.6671(3) 0.8912(3) 0.0604(13) Uani 1 1 d . . . . .
C13 C 0.0101(5) 0.8940(3) 1.0444(3) 0.0344(11) Uani 1 1 d . . . . .
O4 O 0.2942(4) 0.7201(3) 0.7624(3) 0.0591(11) Uani 1 1 d . . . . .
N2 N -0.1919(4) 0.8851(3) 0.9269(3) 0.0379(10) Uani 1 1 d . . . . .
N3 N 0.2564(5) 0.7563(4) 0.6868(4) 0.0542(13) Uani 1 1 d . . . . .
C1 C -0.0733(6) 0.9444(4) 0.6792(3) 0.0400(13) Uani 1 1 d . . . . .
C16 C 0.2705(5) 0.8736(4) 1.1255(4) 0.0442(14) Uani 1 1 d . . . . .
H16 H 0.357584 0.866707 1.152556 0.053 Uiso 1 1 calc R U . . .
N1 N -0.2858(4) 0.8689(3) 0.7341(3) 0.0407(11) Uani 1 1 d . . . . .
C18 C 0.0866(5) 0.8676(3) 0.9949(3) 0.0320(11) Uani 1 1 d . . . . .
N5 N 0.3276(5) 0.9758(4) 0.8543(4) 0.0544(13) Uani 1 1 d . . . . .
O11 O 0.4012(5) 1.0403(4) 0.8740(4) 0.0952(19) Uani 1 1 d . . . . .
N4 N 0.0774(7) 0.6342(4) 0.8364(4) 0.0701(18) Uani 1 1 d . . . . .
C17 C 0.2185(5) 0.8566(4) 1.0359(3) 0.0367(12) Uani 1 1 d . . . . .
C15 C 0.1937(6) 0.9007(4) 1.1745(4) 0.0472(15) Uani 1 1 d . . . . .
H15 H 0.229019 0.912971 1.234265 0.057 Uiso 1 1 calc R U . . .
C4 C -0.1518(9) 1.0677(5) 0.5379(5) 0.079(2) Uani 1 1 d . . . . .
H4 H -0.179289 1.110118 0.491695 0.094 Uiso 1 1 calc R U . . .
C6 C -0.2030(6) 0.9511(4) 0.6325(3) 0.0458(14) Uani 1 1 d . . . . .
C2 C 0.0130(7) 0.9983(4) 0.6534(4) 0.0518(15) Uani 1 1 d . . . . .
H2 H 0.099081 0.993392 0.684595 0.062 Uiso 1 1 calc R U . . .
C12 C -0.1283(5) 0.8958(3) 1.0075(3) 0.0357(12) Uani 1 1 d . . . . .
H12 H -0.174048 0.905539 1.046528 0.043 Uiso 1 1 calc R U . . .
C14 C 0.0650(6) 0.9095(4) 1.1347(4) 0.0433(13) Uani 1 1 d . . . . .
H14 H 0.013338 0.925999 1.168259 0.052 Uiso 1 1 calc R U . . .
O5 O 0.3019(6) 0.7391(4) 0.6294(4) 0.0858(17) Uani 1 1 d . . . . .
C10 C -0.3749(6) 0.7947(4) 0.8428(5) 0.0536(16) Uani 1 1 d . . . . .
H10A H -0.311010 0.745676 0.858856 0.064 Uiso 1 1 calc R U . . .
H10B H -0.453202 0.769120 0.848485 0.064 Uiso 1 1 calc R U . . .
C19 C 0.4062(6) 0.7851(5) 1.0209(4) 0.0547(16) Uani 1 1 d . . . . .
H19A H 0.395628 0.732201 1.055022 0.082 Uiso 1 1 calc R U . . .
H19B H 0.463622 0.829220 1.058377 0.082 Uiso 1 1 calc R U . . .
H19C H 0.440223 0.764339 0.975813 0.082 Uiso 1 1 calc R U . . .
C3 C -0.0251(9) 1.0593(5) 0.5827(5) 0.068(2) Uani 1 1 d . . . . .
H3 H 0.034627 1.094005 0.566010 0.082 Uiso 1 1 calc R U . . .
C11 C -0.3320(5) 0.8760(5) 0.9067(4) 0.0500(15) Uani 1 1 d . . . . .
H11A H -0.374047 0.933481 0.880477 0.060 Uiso 1 1 calc R U . . .
H11B H -0.353066 0.863892 0.960099 0.060 Uiso 1 1 calc R U . . .
C5 C -0.2378(8) 1.0138(5) 0.5611(4) 0.067(2) Uani 1 1 d . . . . .
H5 H -0.323251 1.018770 0.528304 0.080 Uiso 1 1 calc R U . . .
C8 C -0.4204(6) 0.8755(5) 0.5811(4) 0.0647(19) Uani 1 1 d . . . . .
H8A H -0.487583 0.915946 0.585247 0.097 Uiso 1 1 calc R U . . .
H8B H -0.444498 0.811275 0.584626 0.097 Uiso 1 1 calc R U . . .
H8C H -0.405304 0.885875 0.526001 0.097 Uiso 1 1 calc R U . . .
C7 C -0.3003(5) 0.8965(4) 0.6558(4) 0.0440(14) 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
Er1 O2 2.275(4) . ?
Er1 O1 2.301(4) . ?
Er1 O6 2.356(5) . ?
Er1 O7 2.378(4) . ?
Er1 O10 2.396(4) . ?
Er1 O12 2.400(4) . ?
Er1 O4 2.413(4) . ?
Er1 O9 2.415(4) . ?
Er1 O3 2.494(4) . ?
Er1 N3 2.809(5) . ?
Er1 N5 2.830(5) . ?
Er1 N4 2.832(5) . ?
Cu1 O1 1.912(4) . ?
Cu1 O2 1.915(4) . ?
Cu1 N2 1.925(5) . ?
Cu1 N1 1.957(4) . ?
O1 C1 1.352(6) . ?
O3 C17 1.368(7) . ?
O3 C19 1.439(7) . ?
O6 N3 1.278(7) . ?
O12 N5 1.283(6) . ?
O2 C18 1.334(6) . ?
O7 N4 1.266(7) . ?
O10 N5 1.255(6) . ?
C9 N1 1.488(8) . ?
C9 C10 1.488(10) . ?
O8 N4 1.195(7) . ?
O9 N4 1.272(7) . ?
C13 C18 1.382(7) . ?
C13 C14 1.400(7) . ?
C13 C12 1.459(7) . ?
O4 N3 1.262(7) . ?
N2 C12 1.272(7) . ?
N2 C11 1.488(7) . ?
N3 O5 1.204(6) . ?
C1 C2 1.387(8) . ?
C1 C6 1.399(8) . ?
C16 C15 1.383(8) . ?
C16 C17 1.389(7) . ?
N1 C7 1.276(7) . ?
C18 C17 1.409(7) . ?
N5 O11 1.204(7) . ?
C15 C14 1.372(8) . ?
C4 C5 1.363(11) . ?
C4 C3 1.366(11) . ?
C6 C5 1.407(8) . ?
C6 C7 1.469(9) . ?
C2 C3 1.385(9) . ?
C10 C11 1.521(9) . ?
C8 C7 1.514(8) . ?

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 Er1 O1 65.60(13) . . ?
O2 Er1 O6 143.98(15) . . ?
O1 Er1 O6 78.72(15) . . ?
O2 Er1 O7 83.36(17) . . ?
O1 Er1 O7 75.45(15) . . ?
O6 Er1 O7 83.16(17) . . ?
O2 Er1 O10 79.74(14) . . ?
O1 Er1 O10 79.23(14) . . ?
O6 Er1 O10 98.92(15) . . ?
O7 Er1 O10 153.68(16) . . ?
O2 Er1 O12 123.72(14) . . ?
O1 Er1 O12 122.23(15) . . ?
O6 Er1 O12 79.06(17) . . ?
O7 Er1 O12 151.17(17) . . ?
O10 Er1 O12 52.90(14) . . ?
O2 Er1 O4 154.63(15) . . ?
O1 Er1 O4 128.76(14) . . ?
O6 Er1 O4 53.33(15) . . ?
O7 Er1 O4 81.40(18) . . ?
O10 Er1 O4 120.94(15) . . ?
O12 Er1 O4 69.78(15) . . ?
O2 Er1 O9 82.09(17) . . ?
O1 Er1 O9 121.79(15) . . ?
O6 Er1 O9 114.82(16) . . ?
O7 Er1 O9 52.87(15) . . ?
O10 Er1 O9 142.40(15) . . ?
O12 Er1 O9 115.96(17) . . ?
O4 Er1 O9 72.54(18) . . ?
O2 Er1 O3 65.77(13) . . ?
O1 Er1 O3 127.32(12) . . ?
O6 Er1 O3 148.79(16) . . ?
O7 Er1 O3 117.25(14) . . ?
O10 Er1 O3 73.45(13) . . ?
O12 Er1 O3 72.27(15) . . ?
O4 Er1 O3 103.92(14) . . ?
O9 Er1 O3 69.10(14) . . ?
O2 Er1 N3 165.27(14) . . ?
O1 Er1 N3 104.72(15) . . ?
O6 Er1 N3 26.86(15) . . ?
O7 Er1 N3 83.38(18) . . ?
O10 Er1 N3 110.22(15) . . ?
O12 Er1 N3 70.56(15) . . ?
O4 Er1 N3 26.60(14) . . ?
O9 Er1 N3 94.94(17) . . ?
O3 Er1 N3 126.68(15) . . ?
O2 Er1 N5 101.22(15) . . ?
O1 Er1 N5 101.54(15) . . ?
O6 Er1 N5 90.11(16) . . ?
O7 Er1 N5 173.04(16) . . ?
O10 Er1 N5 26.13(14) . . ?
O12 Er1 N5 26.82(14) . . ?
O4 Er1 N5 96.03(16) . . ?
O9 Er1 N5 132.58(16) . . ?
O3 Er1 N5 69.62(14) . . ?
N3 Er1 N5 91.43(15) . . ?
O2 Er1 N4 81.73(18) . . ?
O1 Er1 N4 98.68(17) . . ?
O6 Er1 N4 99.70(17) . . ?
O7 Er1 N4 26.31(16) . . ?
O10 Er1 N4 160.46(17) . . ?
O12 Er1 N4 137.38(18) . . ?
O4 Er1 N4 75.63(19) . . ?
O9 Er1 N4 26.56(16) . . ?
O3 Er1 N4 93.29(15) . . ?
N3 Er1 N4 89.17(18) . . ?
N5 Er1 N4 158.92(17) . . ?
O1 Cu1 O2 80.75(16) . . ?
O1 Cu1 N2 167.41(18) . . ?
O2 Cu1 N2 90.82(17) . . ?
O1 Cu1 N1 91.97(18) . . ?
O2 Cu1 N1 163.03(17) . . ?
N2 Cu1 N1 98.6(2) . . ?
O1 Cu1 Er1 41.77(10) . . ?
O2 Cu1 Er1 41.00(11) . . ?
N2 Cu1 Er1 131.55(13) . . ?
N1 Cu1 Er1 126.83(14) . . ?
C1 O1 Cu1 118.3(3) . . ?
C1 O1 Er1 135.1(3) . . ?
Cu1 O1 Er1 104.62(15) . . ?
C17 O3 C19 117.0(4) . . ?
C17 O3 Er1 116.8(3) . . ?
C19 O3 Er1 123.8(4) . . ?
N3 O6 Er1 96.7(4) . . ?
N5 O12 Er1 95.6(3) . . ?
C18 O2 Cu1 128.2(3) . . ?
C18 O2 Er1 124.8(3) . . ?
Cu1 O2 Er1 105.50(15) . . ?
N4 O7 Er1 97.3(4) . . ?
N5 O10 Er1 96.6(3) . . ?
N1 C9 C10 113.7(5) . . ?
N4 O9 Er1 95.3(3) . . ?
C18 C13 C14 119.4(5) . . ?
C18 C13 C12 121.8(5) . . ?
C14 C13 C12 118.4(5) . . ?
N3 O4 Er1 94.5(3) . . ?
C12 N2 C11 116.0(5) . . ?
C12 N2 Cu1 126.6(4) . . ?
C11 N2 Cu1 117.4(4) . . ?
O5 N3 O4 123.8(6) . . ?
O5 N3 O6 121.3(6) . . ?
O4 N3 O6 114.9(5) . . ?
O5 N3 Er1 172.9(4) . . ?
O4 N3 Er1 58.9(3) . . ?
O6 N3 Er1 56.4(3) . . ?
O1 C1 C2 118.9(5) . . ?
O1 C1 C6 121.7(5) . . ?
C2 C1 C6 119.4(5) . . ?
C15 C16 C17 120.4(5) . . ?
C7 N1 C9 116.6(5) . . ?
C7 N1 Cu1 123.7(4) . . ?
C9 N1 Cu1 119.5(4) . . ?
O2 C18 C13 123.0(5) . . ?
O2 C18 C17 117.4(5) . . ?
C13 C18 C17 119.6(5) . . ?
O11 N5 O10 123.8(5) . . ?
O11 N5 O12 121.5(6) . . ?
O10 N5 O12 114.7(5) . . ?
O11 N5 Er1 175.5(5) . . ?
O10 N5 Er1 57.2(3) . . ?
O12 N5 Er1 57.6(3) . . ?
O8 N4 O7 121.9(6) . . ?
O8 N4 O9 123.6(6) . . ?
O7 N4 O9 114.5(5) . . ?
O8 N4 Er1 177.6(6) . . ?
O7 N4 Er1 56.4(3) . . ?
O9 N4 Er1 58.1(3) . . ?
O3 C17 C16 125.5(5) . . ?
O3 C17 C18 114.7(4) . . ?
C16 C17 C18 119.7(5) . . ?
C14 C15 C16 119.7(5) . . ?
C5 C4 C3 119.8(7) . . ?
C1 C6 C5 116.8(6) . . ?
C1 C6 C7 122.6(5) . . ?
C5 C6 C7 120.5(6) . . ?
C3 C2 C1 122.1(7) . . ?
N2 C12 C13 125.8(5) . . ?
C15 C14 C13 121.1(5) . . ?
C9 C10 C11 113.5(5) . . ?
C4 C3 C2 118.9(7) . . ?
N2 C11 C10 107.3(5) . . ?
C4 C5 C6 122.9(7) . . ?
N1 C7 C6 122.5(5) . . ?
N1 C7 C8 121.7(6) . . ?
C6 C7 C8 115.8(5) . . ?

_refine_diff_density_max         1.652
_refine_diff_density_min         -1.149
_refine_diff_density_rms         0.146

