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

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

data_1
_database_code_depnum_ccdc_archive 'CCDC 1839664'
_audit_update_record             
;
2018-04-26 deposited with the CCDC.
2018-07-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H54 Dy2 N4 O10'
_chemical_formula_weight         1123.91

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'
Dy Dy -0.1892 4.4098 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.558(4)
_cell_length_b                   14.564(5)
_cell_length_c                   15.271(5)
_cell_angle_alpha                90
_cell_angle_beta                 109.552(4)
_cell_angle_gamma                90
_cell_volume                     2422.5(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4696
_cell_measurement_theta_min      2.34
_cell_measurement_theta_max      26.45

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_F_000             1116
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    3.116
_shelx_estimated_absorpt_T_min   0.561
_shelx_estimated_absorpt_T_max   0.652
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5607
_exptl_absorpt_correction_T_max  0.6522
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'APEX2 CCD detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12854
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_av_R_equivalents  0.0467
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.831
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_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             4913
_reflns_number_gt                3756
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0772P)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         4913
_refine_ls_number_parameters     276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0612
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1260
_refine_ls_wR_factor_gt          0.1188
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_restrained_S_all      0.991
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2121(5) 0.9274(4) 0.0081(4) 0.0445(13) Uani 1 1 d . . . . .
C2 C 0.2691(6) 0.8601(4) 0.0737(4) 0.0518(15) Uani 1 1 d . . . . .
C3 C 0.3804(7) 0.8200(5) 0.0730(5) 0.068(2) Uani 1 1 d . . . . .
H3 H 0.416355 0.773941 0.115656 0.082 Uiso 1 1 calc R U . . .
C4 C 0.4368(6) 0.8472(6) 0.0110(5) 0.069(2) Uani 1 1 d . . . . .
C5 C 0.3827(6) 0.9180(6) -0.0488(5) 0.069(2) Uani 1 1 d . . . . .
H5 H 0.423748 0.941305 -0.086956 0.083 Uiso 1 1 calc R U . . .
C6 C 0.2719(6) 0.9556(5) -0.0549(5) 0.0554(16) Uani 1 1 d . . . . .
C7 C 0.2198(7) 0.8260(4) 0.1439(5) 0.0605(18) Uani 1 1 d . . . . .
H7 H 0.248658 0.769129 0.169759 0.073 Uiso 1 1 calc R U . . .
C8 C 0.1167(8) 0.8175(5) 0.2495(5) 0.0668(19) Uani 1 1 d . . . . .
H8A H 0.152408 0.852295 0.306358 0.080 Uiso 1 1 calc R U . . .
H8B H 0.156699 0.757962 0.258287 0.080 Uiso 1 1 calc R U . . .
C9 C -0.0168(9) 0.8039(5) 0.2335(6) 0.079(2) Uani 1 1 d . . . . .
H9A H -0.025367 0.757708 0.276753 0.095 Uiso 1 1 calc R U . . .
H9B H -0.055125 0.779898 0.171262 0.095 Uiso 1 1 calc R U . . .
C10 C -0.0862(8) 0.8896(5) 0.2444(5) 0.070(2) Uani 1 1 d . . . . .
H10A H -0.163949 0.871421 0.250401 0.084 Uiso 1 1 calc R U . . .
H10B H -0.039102 0.921068 0.301050 0.084 Uiso 1 1 calc R U . . .
C11 C -0.2195(7) 0.9796(5) 0.1281(5) 0.0641(19) Uani 1 1 d . . . . .
H11 H -0.275443 0.952217 0.151803 0.077 Uiso 1 1 calc R U . . .
C12 C 0.5559(7) 0.8024(8) 0.0102(7) 0.100(3) Uani 1 1 d . . . . .
H12A H 0.609597 0.848543 0.000354 0.150 Uiso 1 1 calc R U . . .
H12B H 0.537840 0.757912 -0.038982 0.150 Uiso 1 1 calc R U . . .
H12C H 0.595229 0.772519 0.068658 0.150 Uiso 1 1 calc R U . . .
C13 C 0.4918(8) 1.0320(6) 0.2657(6) 0.077(2) Uani 1 1 d . . . . .
H13A H 0.499962 0.980093 0.229485 0.115 Uiso 1 1 calc R U . . .
H13B H 0.546085 1.024923 0.328504 0.115 Uiso 1 1 calc R U . . .
H13C H 0.512615 1.087063 0.239678 0.115 Uiso 1 1 calc R U . . .
C14 C 0.3621(7) 1.0383(4) 0.2647(5) 0.0530(16) Uani 1 1 d . . . . .
C15 C 0.3413(7) 1.0421(4) 0.3493(5) 0.0576(17) Uani 1 1 d . . . . .
H15 H 0.409480 1.043022 0.403247 0.069 Uiso 1 1 calc R U . . .
C16 C 0.2251(7) 1.0446(4) 0.3591(5) 0.0567(17) Uani 1 1 d . . . . .
C17 C 0.2134(9) 1.0520(6) 0.4545(5) 0.079(2) Uani 1 1 d . . . . .
H17A H 0.149532 1.011626 0.458237 0.119 Uiso 1 1 calc R U . . .
H17B H 0.193431 1.114036 0.465064 0.119 Uiso 1 1 calc R U . . .
H17C H 0.289728 1.034902 0.500651 0.119 Uiso 1 1 calc R U . . .
C18 C -0.1583(7) 1.2841(5) 0.1737(6) 0.076(2) Uani 1 1 d . . . . .
H18A H -0.133385 1.284914 0.240266 0.114 Uiso 1 1 calc R U . . .
H18B H -0.234327 1.251158 0.148982 0.114 Uiso 1 1 calc R U . . .
H18C H -0.169266 1.345889 0.150548 0.114 Uiso 1 1 calc R U . . .
C19 C -0.0609(6) 1.2372(4) 0.1441(5) 0.0532(15) Uani 1 1 d . . . . .
C20 C -0.0004(7) 1.2843(4) 0.0934(5) 0.0634(18) Uani 1 1 d . . . . .
H20 H -0.020468 1.345827 0.080809 0.076 Uiso 1 1 calc R U . . .
C21 C 0.0870(6) 1.2482(4) 0.0599(4) 0.0522(15) Uani 1 1 d . . . . .
C22 C 0.1441(7) 1.3097(5) 0.0098(5) 0.0640(18) Uani 1 1 d . . . . .
H22A H 0.214235 1.279970 0.002101 0.096 Uiso 1 1 calc R U . . .
H22B H 0.169588 1.365283 0.044681 0.096 Uiso 1 1 calc R U . . .
H22C H 0.085787 1.323944 -0.050107 0.096 Uiso 1 1 calc R U . . .
Dy1 Dy 0.06726(3) 1.03264(2) 0.13068(2) 0.04150(13) Uani 1 1 d . . . . .
N1 N 0.1419(5) 0.8652(3) 0.1737(3) 0.0533(13) Uani 1 1 d . . . . .
N2 N -0.1100(5) 0.9538(4) 0.1654(4) 0.0525(13) Uani 1 1 d . . . . .
O1 O 0.1062(4) 0.9641(2) 0.0055(3) 0.0449(9) Uani 1 1 d . . . . .
O2 O 0.2798(4) 1.0413(3) 0.1868(3) 0.0546(11) Uani 1 1 d . . . . .
O3 O 0.1261(4) 1.0404(3) 0.2917(3) 0.0570(11) Uani 1 1 d . . . . .
O4 O -0.0419(4) 1.1529(3) 0.1681(3) 0.0539(10) Uani 1 1 d . . . . .
O5 O 0.1199(4) 1.1652(3) 0.0684(3) 0.0568(11) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.324(7) . ?
C1 C2 1.399(9) . ?
C1 C6 1.420(9) . ?
C2 C3 1.416(9) . ?
C2 C7 1.459(10) . ?
C3 C4 1.376(11) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(11) . ?
C4 C12 1.527(10) . ?
C5 C6 1.367(10) . ?
C5 H5 0.9300 . ?
C6 C11 1.434(10) 3_575 ?
C7 N1 1.273(9) . ?
C7 H7 0.9300 . ?
C8 N1 1.461(8) . ?
C8 C9 1.492(12) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.523(11) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N2 1.477(8) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N2 1.259(9) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.498(11) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 O2 1.252(8) . ?
C14 C15 1.392(10) . ?
C15 C16 1.401(11) . ?
C15 H15 0.9300 . ?
C16 O3 1.258(8) . ?
C16 C17 1.511(10) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.509(9) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 O4 1.279(7) . ?
C19 C20 1.386(9) . ?
C20 C21 1.380(9) . ?
C20 H20 0.9300 . ?
C21 O5 1.260(7) . ?
C21 C22 1.470(9) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
Dy1 O2 2.319(5) . ?
Dy1 O5 2.321(4) . ?
Dy1 O3 2.324(5) . ?
Dy1 O1 2.331(4) . ?
Dy1 O4 2.339(4) . ?
Dy1 O1 2.357(4) 3_575 ?
Dy1 N2 2.554(6) . ?
Dy1 N1 2.596(5) . ?
Dy1 Dy1 3.8857(13) 3_575 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 120.9(5) . . ?
O1 C1 C6 121.2(5) . . ?
C2 C1 C6 117.9(6) . . ?
C1 C2 C3 119.7(6) . . ?
C1 C2 C7 123.9(6) . . ?
C3 C2 C7 116.3(6) . . ?
C4 C3 C2 121.8(7) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 117.2(7) . . ?
C3 C4 C12 121.2(8) . . ?
C5 C4 C12 121.6(8) . . ?
C6 C5 C4 123.4(7) . . ?
C6 C5 H5 118.3 . . ?
C4 C5 H5 118.3 . . ?
C5 C6 C1 119.7(7) . . ?
C5 C6 C11 117.2(7) . 3_575 ?
C1 C6 C11 123.0(6) . 3_575 ?
N1 C7 C2 127.4(6) . . ?
N1 C7 H7 116.3 . . ?
C2 C7 H7 116.3 . . ?
N1 C8 C9 113.7(6) . . ?
N1 C8 H8A 108.8 . . ?
C9 C8 H8A 108.8 . . ?
N1 C8 H8B 108.8 . . ?
C9 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C8 C9 C10 115.3(6) . . ?
C8 C9 H9A 108.5 . . ?
C10 C9 H9A 108.5 . . ?
C8 C9 H9B 108.5 . . ?
C10 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
N2 C10 C9 113.0(6) . . ?
N2 C10 H10A 109.0 . . ?
C9 C10 H10A 109.0 . . ?
N2 C10 H10B 109.0 . . ?
C9 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
N2 C11 C6 130.4(7) . 3_575 ?
N2 C11 H11 114.8 . . ?
C6 C11 H11 114.8 3_575 . ?
C4 C12 H12A 109.5 . . ?
C4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C14 C15 124.7(7) . . ?
O2 C14 C13 116.8(7) . . ?
C15 C14 C13 118.5(7) . . ?
C14 C15 C16 124.7(6) . . ?
C14 C15 H15 117.7 . . ?
C16 C15 H15 117.7 . . ?
O3 C16 C15 123.6(7) . . ?
O3 C16 C17 116.2(7) . . ?
C15 C16 C17 120.2(7) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C19 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O4 C19 C20 124.3(6) . . ?
O4 C19 C18 115.0(6) . . ?
C20 C19 C18 120.7(6) . . ?
C21 C20 C19 126.0(6) . . ?
C21 C20 H20 117.0 . . ?
C19 C20 H20 117.0 . . ?
O5 C21 C20 124.0(6) . . ?
O5 C21 C22 117.8(6) . . ?
C20 C21 C22 118.2(6) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O2 Dy1 O5 73.46(15) . . ?
O2 Dy1 O3 73.02(17) . . ?
O5 Dy1 O3 111.63(16) . . ?
O2 Dy1 O1 81.66(16) . . ?
O5 Dy1 O1 82.62(14) . . ?
O3 Dy1 O1 145.13(14) . . ?
O2 Dy1 O4 117.41(15) . . ?
O5 Dy1 O4 73.36(16) . . ?
O3 Dy1 O4 72.29(15) . . ?
O1 Dy1 O4 142.12(14) . . ?
O2 Dy1 O1 143.89(15) . 3_575 ?
O5 Dy1 O1 83.33(15) . 3_575 ?
O3 Dy1 O1 142.53(16) . 3_575 ?
O1 Dy1 O1 68.01(17) . 3_575 ?
O4 Dy1 O1 80.28(14) . 3_575 ?
O2 Dy1 N2 140.55(16) . . ?
O5 Dy1 N2 142.88(16) . . ?
O3 Dy1 N2 76.91(16) . . ?
O1 Dy1 N2 111.46(16) . . ?
O4 Dy1 N2 75.56(16) . . ?
O1 Dy1 N2 71.81(16) 3_575 . ?
O2 Dy1 N1 74.73(16) . . ?
O5 Dy1 N1 140.73(16) . . ?
O3 Dy1 N1 79.84(15) . . ?
O1 Dy1 N1 70.49(14) . . ?
O4 Dy1 N1 143.37(15) . . ?
O1 Dy1 N1 110.78(15) 3_575 . ?
N2 Dy1 N1 75.34(18) . . ?
O2 Dy1 Dy1 113.76(11) . 3_575 ?
O5 Dy1 Dy1 81.51(12) . 3_575 ?
O3 Dy1 Dy1 166.77(11) . 3_575 ?
O1 Dy1 Dy1 34.22(10) . 3_575 ?
O4 Dy1 Dy1 111.78(10) . 3_575 ?
O1 Dy1 Dy1 33.79(10) 3_575 3_575 ?
N2 Dy1 Dy1 91.73(12) . 3_575 ?
N1 Dy1 Dy1 90.85(11) . 3_575 ?
C7 N1 C8 115.0(6) . . ?
C7 N1 Dy1 123.1(4) . . ?
C8 N1 Dy1 120.7(4) . . ?
C11 N2 C10 116.3(6) . . ?
C11 N2 Dy1 121.8(4) . . ?
C10 N2 Dy1 120.7(4) . . ?
C1 O1 Dy1 125.3(3) . . ?
C1 O1 Dy1 122.7(3) . 3_575 ?
Dy1 O1 Dy1 111.99(17) . 3_575 ?
C14 O2 Dy1 136.3(5) . . ?
C16 O3 Dy1 137.0(5) . . ?
C19 O4 Dy1 134.8(4) . . ?
C21 O5 Dy1 136.8(4) . . ?

_refine_diff_density_max         2.065
_refine_diff_density_min         -0.962
_refine_diff_density_rms         0.138

####################################################################### 
# 
# 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 1839666'
_audit_update_record             
;
2018-04-26 deposited with the CCDC.
2018-07-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H54 Ho2 N4 O10'
_chemical_formula_weight         1128.77

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'
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                   11.6290(19)
_cell_length_b                   14.544(2)
_cell_length_c                   15.311(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.493(2)
_cell_angle_gamma                90
_cell_volume                     2441.3(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5937
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      27.53

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.240
_exptl_absorpt_coefficient_mu    3.272
_shelx_estimated_absorpt_T_min   0.440
_shelx_estimated_absorpt_T_max   0.507
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4402
_exptl_absorpt_correction_T_max  0.5073
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13118
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.326
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4960
_reflns_number_gt                3999
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0482P)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         4960
_refine_ls_number_parameters     276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0446
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0841
_refine_ls_wR_factor_gt          0.0801
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_restrained_S_all      0.992
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2113(4) -0.0715(3) 0.0086(3) 0.0418(9) Uani 1 1 d . . . . .
C2 C 0.2690(4) -0.1390(3) 0.0742(3) 0.0480(10) Uani 1 1 d . . . . .
C3 C 0.3784(4) -0.1788(3) 0.0730(3) 0.0578(12) Uani 1 1 d . . . . .
H3 H 0.413115 -0.225684 0.114863 0.069 Uiso 1 1 calc R U . . .
C4 C 0.4374(4) -0.1508(4) 0.0114(3) 0.0636(14) Uani 1 1 d . . . . .
C5 C 0.3816(4) -0.0818(4) -0.0496(3) 0.0598(12) Uani 1 1 d . . . . .
H5 H 0.420575 -0.059584 -0.089432 0.072 Uiso 1 1 calc R U . . .
C6 C 0.2694(4) -0.0433(3) -0.0547(3) 0.0487(10) Uani 1 1 d . . . . .
C7 C 0.2207(4) -0.1735(3) 0.1443(3) 0.0536(11) Uani 1 1 d . . . . .
H7 H 0.250049 -0.230209 0.170343 0.064 Uiso 1 1 calc R U . . .
C8 C 0.1203(5) -0.1829(4) 0.2507(3) 0.0633(13) Uani 1 1 d . . . . .
H8A H 0.157572 -0.148451 0.307378 0.076 Uiso 1 1 calc R U . . .
H8B H 0.159599 -0.242616 0.258241 0.076 Uiso 1 1 calc R U . . .
C9 C -0.0156(5) -0.1965(3) 0.2367(3) 0.0684(14) Uani 1 1 d . . . . .
H9A H -0.054982 -0.222370 0.175575 0.082 Uiso 1 1 calc R U . . .
H9B H -0.022920 -0.241155 0.281651 0.082 Uiso 1 1 calc R U . . .
C10 C -0.0833(5) -0.1109(4) 0.2457(3) 0.0601(13) Uani 1 1 d . . . . .
H10A H -0.160659 -0.128453 0.252011 0.072 Uiso 1 1 calc R U . . .
H10B H -0.036448 -0.078930 0.301942 0.072 Uiso 1 1 calc R U . . .
C11 C -0.2177(4) -0.0227(3) 0.1290(3) 0.0546(12) Uani 1 1 d . . . . .
H11 H -0.273142 -0.051003 0.152281 0.065 Uiso 1 1 calc R U . . .
C12 C 0.5529(5) -0.1961(5) 0.0106(4) 0.0882(19) Uani 1 1 d . . . . .
H12A H 0.593002 -0.157383 -0.021089 0.132 Uiso 1 1 calc R U . . .
H12B H 0.533865 -0.254193 -0.020795 0.132 Uiso 1 1 calc R U . . .
H12C H 0.605697 -0.205874 0.073116 0.132 Uiso 1 1 calc R U . . .
C13 C 0.4894(5) 0.0312(4) 0.2637(4) 0.0718(15) Uani 1 1 d . . . . .
H13A H 0.497348 -0.022321 0.229518 0.108 Uiso 1 1 calc R U . . .
H13B H 0.544470 0.026558 0.326249 0.108 Uiso 1 1 calc R U . . .
H13C H 0.508577 0.085094 0.235111 0.108 Uiso 1 1 calc R U . . .
C14 C 0.3595(4) 0.0380(3) 0.2643(3) 0.0496(11) Uani 1 1 d . . . . .
C15 C 0.3393(4) 0.0415(3) 0.3483(3) 0.0572(12) Uani 1 1 d . . . . .
H15 H 0.407039 0.041698 0.402034 0.069 Uiso 1 1 calc R U . . .
C16 C 0.2248(4) 0.0447(3) 0.3578(3) 0.0481(10) Uani 1 1 d . . . . .
C17 C 0.2137(6) 0.0529(4) 0.4539(3) 0.0736(16) Uani 1 1 d . . . . .
H17A H 0.151592 0.011687 0.458703 0.110 Uiso 1 1 calc R U . . .
H17B H 0.192361 0.114849 0.463725 0.110 Uiso 1 1 calc R U . . .
H17C H 0.290269 0.037208 0.499932 0.110 Uiso 1 1 calc R U . . .
C18 C -0.1573(5) 0.2842(4) 0.1728(4) 0.0698(14) Uani 1 1 d . . . . .
H18A H -0.133890 0.283721 0.239124 0.105 Uiso 1 1 calc R U . . .
H18B H -0.233950 0.253142 0.146630 0.105 Uiso 1 1 calc R U . . .
H18C H -0.165159 0.346654 0.151148 0.105 Uiso 1 1 calc R U . . .
C19 C -0.0609(4) 0.2357(3) 0.1435(3) 0.0483(10) Uani 1 1 d . . . . .
C20 C -0.0011(4) 0.2830(3) 0.0934(4) 0.0605(12) Uani 1 1 d . . . . .
H20 H -0.020657 0.344764 0.081356 0.073 Uiso 1 1 calc R U . . .
C21 C 0.0860(4) 0.2464(3) 0.0594(3) 0.0474(10) Uani 1 1 d . . . . .
C22 C 0.1448(5) 0.3089(3) 0.0085(3) 0.0591(12) Uani 1 1 d . . . . .
H22A H 0.209585 0.276693 -0.004097 0.089 Uiso 1 1 calc R U . . .
H22B H 0.177235 0.361907 0.045966 0.089 Uiso 1 1 calc R U . . .
H22C H 0.085113 0.327937 -0.048736 0.089 Uiso 1 1 calc R U . . .
Ho1 Ho 0.06688(2) 0.03211(2) 0.13044(2) 0.03800(8) Uani 1 1 d . . . . .
N1 N 0.1426(3) -0.1346(3) 0.1741(2) 0.0501(9) Uani 1 1 d . . . . .
N2 N -0.1070(3) -0.0468(2) 0.1664(2) 0.0465(9) Uani 1 1 d . . . . .
O1 O 0.1051(2) -0.03543(18) 0.00549(18) 0.0411(6) Uani 1 1 d . . . . .
O2 O 0.2780(3) 0.0413(2) 0.1861(2) 0.0515(8) Uani 1 1 d . . . . .
O3 O 0.1250(3) 0.0406(2) 0.2907(2) 0.0535(8) Uani 1 1 d . . . . .
O4 O -0.0421(3) 0.1526(2) 0.16741(19) 0.0489(7) Uani 1 1 d . . . . .
O5 O 0.1184(3) 0.1641(2) 0.0678(2) 0.0534(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.328(5) . ?
C1 C2 1.406(6) . ?
C1 C6 1.414(6) . ?
C2 C3 1.403(6) . ?
C2 C7 1.457(6) . ?
C3 C4 1.400(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.377(7) . ?
C4 C12 1.500(7) . ?
C5 C6 1.398(6) . ?
C5 H5 0.9300 . ?
C6 C11 1.457(6) 3 ?
C7 N1 1.276(5) . ?
C7 H7 0.9300 . ?
C8 N1 1.462(5) . ?
C8 C9 1.536(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.504(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N2 1.482(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N2 1.271(6) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.517(7) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 O2 1.256(5) . ?
C14 C15 1.383(7) . ?
C15 C16 1.387(7) . ?
C15 H15 0.9300 . ?
C16 O3 1.270(5) . ?
C16 C17 1.524(7) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.514(6) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 O4 1.261(5) . ?
C19 C20 1.378(6) . ?
C20 C21 1.390(6) . ?
C20 H20 0.9300 . ?
C21 O5 1.248(5) . ?
C21 C22 1.502(6) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
Ho1 O5 2.312(3) . ?
Ho1 O2 2.319(3) . ?
Ho1 O3 2.321(3) . ?
Ho1 O1 2.321(3) . ?
Ho1 O4 2.340(3) . ?
Ho1 O1 2.357(3) 3 ?
Ho1 N2 2.540(4) . ?
Ho1 N1 2.590(4) . ?
Ho1 Ho1 3.8860(7) 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 C1 C2 121.2(4) . . ?
O1 C1 C6 120.8(4) . . ?
C2 C1 C6 117.9(4) . . ?
C3 C2 C1 119.9(4) . . ?
C3 C2 C7 116.2(4) . . ?
C1 C2 C7 123.9(4) . . ?
C4 C3 C2 122.6(5) . . ?
C4 C3 H3 118.7 . . ?
C2 C3 H3 118.7 . . ?
C5 C4 C3 116.3(4) . . ?
C5 C4 C12 122.4(5) . . ?
C3 C4 C12 121.3(5) . . ?
C4 C5 C6 123.3(5) . . ?
C4 C5 H5 118.4 . . ?
C6 C5 H5 118.4 . . ?
C5 C6 C1 119.8(4) . . ?
C5 C6 C11 116.1(4) . 3 ?
C1 C6 C11 124.0(4) . 3 ?
N1 C7 C2 127.3(4) . . ?
N1 C7 H7 116.3 . . ?
C2 C7 H7 116.3 . . ?
N1 C8 C9 113.6(4) . . ?
N1 C8 H8A 108.9 . . ?
C9 C8 H8A 108.9 . . ?
N1 C8 H8B 108.9 . . ?
C9 C8 H8B 108.9 . . ?
H8A C8 H8B 107.7 . . ?
C10 C9 C8 115.2(4) . . ?
C10 C9 H9A 108.5 . . ?
C8 C9 H9A 108.5 . . ?
C10 C9 H9B 108.5 . . ?
C8 C9 H9B 108.5 . . ?
H9A C9 H9B 107.5 . . ?
N2 C10 C9 113.9(4) . . ?
N2 C10 H10A 108.8 . . ?
C9 C10 H10A 108.8 . . ?
N2 C10 H10B 108.8 . . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
N2 C11 C6 128.7(4) . 3 ?
N2 C11 H11 115.6 . . ?
C6 C11 H11 115.6 3 . ?
C4 C12 H12A 109.5 . . ?
C4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C14 C15 125.3(4) . . ?
O2 C14 C13 115.6(4) . . ?
C15 C14 C13 119.1(4) . . ?
C14 C15 C16 124.4(4) . . ?
C14 C15 H15 117.8 . . ?
C16 C15 H15 117.8 . . ?
O3 C16 C15 124.3(4) . . ?
O3 C16 C17 115.9(5) . . ?
C15 C16 C17 119.8(4) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C19 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O4 C19 C20 124.7(4) . . ?
O4 C19 C18 115.7(4) . . ?
C20 C19 C18 119.6(4) . . ?
C19 C20 C21 125.7(4) . . ?
C19 C20 H20 117.2 . . ?
C21 C20 H20 117.2 . . ?
O5 C21 C20 124.1(4) . . ?
O5 C21 C22 117.4(4) . . ?
C20 C21 C22 118.5(4) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O5 Ho1 O2 73.47(10) . . ?
O5 Ho1 O3 111.71(11) . . ?
O2 Ho1 O3 73.10(11) . . ?
O5 Ho1 O1 82.08(10) . . ?
O2 Ho1 O1 81.78(10) . . ?
O3 Ho1 O1 145.65(10) . . ?
O5 Ho1 O4 73.43(10) . . ?
O2 Ho1 O4 117.41(11) . . ?
O3 Ho1 O4 72.21(10) . . ?
O1 Ho1 O4 141.64(9) . . ?
O5 Ho1 O1 82.96(10) . 3 ?
O2 Ho1 O1 143.67(10) . 3 ?
O3 Ho1 O1 142.61(10) . 3 ?
O1 Ho1 O1 67.67(11) . 3 ?
O4 Ho1 O1 80.21(10) . 3 ?
O5 Ho1 N2 143.14(11) . . ?
O2 Ho1 N2 140.21(11) . . ?
O3 Ho1 N2 76.53(11) . . ?
O1 Ho1 N2 111.86(11) . . ?
O4 Ho1 N2 75.61(10) . . ?
O1 Ho1 N2 72.46(10) 3 . ?
O5 Ho1 N1 140.49(11) . . ?
O2 Ho1 N1 74.46(11) . . ?
O3 Ho1 N1 79.80(11) . . ?
O1 Ho1 N1 71.02(10) . . ?
O4 Ho1 N1 143.46(10) . . ?
O1 Ho1 N1 111.25(10) 3 . ?
N2 Ho1 N1 75.37(12) . . ?
O5 Ho1 Ho1 80.99(8) . 3 ?
O2 Ho1 Ho1 113.78(8) . 3 ?
O3 Ho1 Ho1 167.18(8) . 3 ?
O1 Ho1 Ho1 34.13(7) . 3 ?
O4 Ho1 Ho1 111.43(7) . 3 ?
O1 Ho1 Ho1 33.55(7) 3 3 ?
N2 Ho1 Ho1 92.27(8) . 3 ?
N1 Ho1 Ho1 91.46(8) . 3 ?
C7 N1 C8 114.3(4) . . ?
C7 N1 Ho1 122.9(3) . . ?
C8 N1 Ho1 121.4(3) . . ?
C11 N2 C10 115.2(4) . . ?
C11 N2 Ho1 122.5(3) . . ?
C10 N2 Ho1 121.2(3) . . ?
C1 O1 Ho1 124.7(2) . . ?
C1 O1 Ho1 123.0(2) . 3 ?
Ho1 O1 Ho1 112.33(11) . 3 ?
C14 O2 Ho1 135.9(3) . . ?
C16 O3 Ho1 136.4(3) . . ?
C19 O4 Ho1 134.7(3) . . ?
C21 O5 Ho1 136.7(3) . . ?

_refine_diff_density_max         2.286
_refine_diff_density_min         -0.629
_refine_diff_density_rms         0.108

####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1839668'
_audit_update_record             
;
2018-04-26 deposited with the CCDC.
2018-07-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H54 Gd2 N4 O10'
_chemical_formula_weight         1113.41

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'
Gd Gd -0.1653 3.9035 '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                   11.576(2)
_cell_length_b                   14.673(3)
_cell_length_c                   15.396(3)
_cell_angle_alpha                90
_cell_angle_beta                 109.464(2)
_cell_angle_gamma                90
_cell_volume                     2465.6(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5701
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      27.19

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_F_000             1108
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    2.721
_shelx_estimated_absorpt_T_min   0.516
_shelx_estimated_absorpt_T_max   0.549
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5163
_exptl_absorpt_correction_T_max  0.5495
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13465
_diffrn_reflns_av_unetI/netI     0.0462
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.973
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5013
_reflns_number_gt                4036
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0509P)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         5013
_refine_ls_number_parameters     276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0356
_refine_ls_wR_factor_ref         0.0926
_refine_ls_wR_factor_gt          0.0875
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2133(4) -0.0714(3) 0.0074(3) 0.0484(9) Uani 1 1 d . . . . .
C2 C 0.2713(4) -0.1389(3) 0.0723(3) 0.0548(10) Uani 1 1 d . . . . .
C3 C 0.3811(4) -0.1791(3) 0.0706(4) 0.0672(13) Uani 1 1 d . . . . .
H3 H 0.415708 -0.226026 0.111603 0.081 Uiso 1 1 calc R U . . .
C4 C 0.4391(4) -0.1509(4) 0.0100(4) 0.0711(14) Uani 1 1 d . . . . .
C5 C 0.3846(4) -0.0826(4) -0.0503(4) 0.0700(13) Uani 1 1 d . . . . .
H5 H 0.424419 -0.060649 -0.089481 0.084 Uiso 1 1 calc R U . . .
C6 C 0.2713(4) -0.0441(3) -0.0558(3) 0.0579(11) Uani 1 1 d . . . . .
C7 C 0.2229(4) -0.1729(3) 0.1424(3) 0.0589(11) Uani 1 1 d . . . . .
H7 H 0.253501 -0.228613 0.168867 0.071 Uiso 1 1 calc R U . . .
C8 C 0.1196(6) -0.1825(3) 0.2483(3) 0.0736(14) Uani 1 1 d . . . . .
H8A H 0.155922 -0.147895 0.304468 0.088 Uiso 1 1 calc R U . . .
H8B H 0.158683 -0.241828 0.256686 0.088 Uiso 1 1 calc R U . . .
C9 C -0.0165(6) -0.1949(3) 0.2321(4) 0.0786(16) Uani 1 1 d . . . . .
H9A H -0.054887 -0.217870 0.170021 0.094 Uiso 1 1 calc R U . . .
H9B H -0.025723 -0.241137 0.274235 0.094 Uiso 1 1 calc R U . . .
C10 C -0.0845(5) -0.1117(3) 0.2434(3) 0.0705(14) Uani 1 1 d . . . . .
H10A H -0.161950 -0.130112 0.249426 0.085 Uiso 1 1 calc R U . . .
H10B H -0.037408 -0.081003 0.299934 0.085 Uiso 1 1 calc R U . . .
C11 C -0.2201(5) -0.0217(3) 0.1292(3) 0.0615(12) Uani 1 1 d . . . . .
H11 H -0.275705 -0.049124 0.152923 0.074 Uiso 1 1 calc R U . . .
C12 C 0.5571(5) -0.1968(5) 0.0096(5) 0.101(2) Uani 1 1 d . . . . .
H12A H 0.602050 -0.155745 -0.015809 0.152 Uiso 1 1 calc R U . . .
H12B H 0.537492 -0.251057 -0.027280 0.152 Uiso 1 1 calc R U . . .
H12C H 0.605971 -0.212408 0.071454 0.152 Uiso 1 1 calc R U . . .
C13 C 0.4955(5) 0.0311(4) 0.2683(4) 0.0809(16) Uani 1 1 d . . . . .
H13A H 0.503289 -0.020957 0.232877 0.121 Uiso 1 1 calc R U . . .
H13B H 0.549825 0.024585 0.330537 0.121 Uiso 1 1 calc R U . . .
H13C H 0.516373 0.085275 0.241779 0.121 Uiso 1 1 calc R U . . .
C14 C 0.3652(4) 0.0381(3) 0.2677(4) 0.0559(11) Uani 1 1 d . . . . .
C15 C 0.3438(5) 0.0417(3) 0.3510(4) 0.0643(13) Uani 1 1 d . . . . .
H15 H 0.411501 0.041958 0.404625 0.077 Uiso 1 1 calc R U . . .
C16 C 0.2282(5) 0.0450(3) 0.3602(3) 0.0542(11) Uani 1 1 d . . . . .
C17 C 0.2151(6) 0.0527(4) 0.4552(4) 0.0820(16) Uani 1 1 d . . . . .
H17A H 0.154131 0.010445 0.459771 0.123 Uiso 1 1 calc R U . . .
H17B H 0.190868 0.113601 0.464044 0.123 Uiso 1 1 calc R U . . .
H17C H 0.292193 0.038947 0.501529 0.123 Uiso 1 1 calc R U . . .
C18 C -0.1590(5) 0.2845(4) 0.1727(4) 0.0818(16) Uani 1 1 d . . . . .
H18A H -0.139472 0.280032 0.238239 0.123 Uiso 1 1 calc R U . . .
H18B H -0.236731 0.255999 0.142528 0.123 Uiso 1 1 calc R U . . .
H18C H -0.163213 0.347586 0.155220 0.123 Uiso 1 1 calc R U . . .
C19 C -0.0608(4) 0.2373(3) 0.1445(3) 0.0552(10) Uani 1 1 d . . . . .
C20 C -0.0008(5) 0.2847(3) 0.0947(4) 0.0664(12) Uani 1 1 d . . . . .
H20 H -0.021140 0.345846 0.082639 0.080 Uiso 1 1 calc R U . . .
C21 C 0.0875(4) 0.2491(3) 0.0609(3) 0.0516(10) Uani 1 1 d . . . . .
C22 C 0.1468(5) 0.3106(3) 0.0108(3) 0.0659(12) Uani 1 1 d . . . . .
H22A H 0.213338 0.279058 -0.000164 0.099 Uiso 1 1 calc R U . . .
H22B H 0.177521 0.363903 0.047297 0.099 Uiso 1 1 calc R U . . .
H22C H 0.087692 0.328248 -0.047031 0.099 Uiso 1 1 calc R U . . .
Gd1 Gd 0.06897(2) 0.03352(2) 0.13101(2) 0.04297(9) Uani 1 1 d . . . . .
N1 N 0.1435(4) -0.1351(2) 0.1716(2) 0.0552(9) Uani 1 1 d . . . . .
N2 N -0.1087(4) -0.0465(2) 0.1653(3) 0.0559(9) Uani 1 1 d . . . . .
O1 O 0.1065(3) -0.03521(16) 0.00456(19) 0.0472(6) Uani 1 1 d . . . . .
O2 O 0.2845(3) 0.04182(19) 0.1894(2) 0.0585(8) Uani 1 1 d . . . . .
O3 O 0.1280(3) 0.04089(19) 0.2929(2) 0.0606(8) Uani 1 1 d . . . . .
O4 O -0.0419(3) 0.1550(2) 0.16777(19) 0.0557(7) Uani 1 1 d . . . . .
O5 O 0.1209(3) 0.1671(2) 0.0694(2) 0.0609(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.333(5) . ?
C1 C2 1.407(6) . ?
C1 C6 1.411(6) . ?
C2 C3 1.410(6) . ?
C2 C7 1.460(6) . ?
C3 C4 1.381(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.370(8) . ?
C4 C12 1.525(7) . ?
C5 C6 1.404(7) . ?
C5 H5 0.9300 . ?
C6 C11 1.454(7) 3 ?
C7 N1 1.276(6) . ?
C7 H7 0.9300 . ?
C8 N1 1.473(6) . ?
C8 C9 1.521(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.493(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N2 1.489(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N2 1.276(6) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.509(7) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 O2 1.256(6) . ?
C14 C15 1.386(7) . ?
C15 C16 1.393(7) . ?
C15 H15 0.9300 . ?
C16 O3 1.274(5) . ?
C16 C17 1.523(7) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.515(6) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 O4 1.257(5) . ?
C19 C20 1.382(6) . ?
C20 C21 1.393(6) . ?
C20 H20 0.9300 . ?
C21 O5 1.258(5) . ?
C21 C22 1.495(6) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
Gd1 O5 2.342(3) . ?
Gd1 O3 2.357(3) . ?
Gd1 O2 2.357(3) . ?
Gd1 O1 2.358(3) . ?
Gd1 O4 2.373(3) . ?
Gd1 O1 2.379(3) 3 ?
Gd1 N2 2.571(4) . ?
Gd1 N1 2.627(3) . ?
Gd1 Gd1 3.9368(8) 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 C1 C2 121.4(4) . . ?
O1 C1 C6 120.8(4) . . ?
C2 C1 C6 117.7(4) . . ?
C1 C2 C3 120.1(4) . . ?
C1 C2 C7 123.7(4) . . ?
C3 C2 C7 116.2(4) . . ?
C4 C3 C2 122.1(5) . . ?
C4 C3 H3 119.0 . . ?
C2 C3 H3 119.0 . . ?
C5 C4 C3 117.4(5) . . ?
C5 C4 C12 122.0(6) . . ?
C3 C4 C12 120.6(6) . . ?
C4 C5 C6 123.0(5) . . ?
C4 C5 H5 118.5 . . ?
C6 C5 H5 118.5 . . ?
C5 C6 C1 119.5(5) . . ?
C5 C6 C11 116.3(5) . 3 ?
C1 C6 C11 124.1(4) . 3 ?
N1 C7 C2 127.7(4) . . ?
N1 C7 H7 116.1 . . ?
C2 C7 H7 116.1 . . ?
N1 C8 C9 112.7(4) . . ?
N1 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
N1 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.8 . . ?
C10 C9 C8 116.2(4) . . ?
C10 C9 H9A 108.2 . . ?
C8 C9 H9A 108.2 . . ?
C10 C9 H9B 108.2 . . ?
C8 C9 H9B 108.2 . . ?
H9A C9 H9B 107.4 . . ?
N2 C10 C9 113.3(4) . . ?
N2 C10 H10A 108.9 . . ?
C9 C10 H10A 108.9 . . ?
N2 C10 H10B 108.9 . . ?
C9 C10 H10B 108.9 . . ?
H10A C10 H10B 107.7 . . ?
N2 C11 C6 128.2(4) . 3 ?
N2 C11 H11 115.9 . . ?
C6 C11 H11 115.9 3 . ?
C4 C12 H12A 109.5 . . ?
C4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C14 C15 125.5(5) . . ?
O2 C14 C13 115.5(5) . . ?
C15 C14 C13 118.9(5) . . ?
C14 C15 C16 124.7(5) . . ?
C14 C15 H15 117.6 . . ?
C16 C15 H15 117.6 . . ?
O3 C16 C15 124.1(4) . . ?
O3 C16 C17 115.5(5) . . ?
C15 C16 C17 120.4(5) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C19 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O4 C19 C20 124.8(4) . . ?
O4 C19 C18 115.7(4) . . ?
C20 C19 C18 119.5(4) . . ?
C19 C20 C21 125.8(4) . . ?
C19 C20 H20 117.1 . . ?
C21 C20 H20 117.1 . . ?
O5 C21 C20 124.0(4) . . ?
O5 C21 C22 116.9(4) . . ?
C20 C21 C22 119.1(4) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O5 Gd1 O3 111.54(11) . . ?
O5 Gd1 O2 74.27(10) . . ?
O3 Gd1 O2 72.40(11) . . ?
O5 Gd1 O1 83.12(9) . . ?
O3 Gd1 O1 145.54(10) . . ?
O2 Gd1 O1 82.75(11) . . ?
O5 Gd1 O4 72.55(10) . . ?
O3 Gd1 O4 72.69(10) . . ?
O2 Gd1 O4 117.27(10) . . ?
O1 Gd1 O4 141.39(9) . . ?
O5 Gd1 O1 83.98(10) . 3 ?
O3 Gd1 O1 142.12(11) . 3 ?
O2 Gd1 O1 145.09(10) . 3 ?
O1 Gd1 O1 67.56(11) . 3 ?
O4 Gd1 O1 80.21(9) . 3 ?
O5 Gd1 N2 142.80(11) . . ?
O3 Gd1 N2 76.91(12) . . ?
O2 Gd1 N2 139.74(11) . . ?
O1 Gd1 N2 110.75(11) . . ?
O4 Gd1 N2 76.18(10) . . ?
O1 Gd1 N2 71.18(11) 3 . ?
O5 Gd1 N1 140.94(11) . . ?
O3 Gd1 N1 80.51(10) . . ?
O2 Gd1 N1 74.68(11) . . ?
O1 Gd1 N1 69.96(10) . . ?
O4 Gd1 N1 144.30(10) . . ?
O1 Gd1 N1 109.60(10) 3 . ?
N2 Gd1 N1 75.09(12) . . ?
O5 Gd1 Gd1 82.24(8) . 3 ?
O3 Gd1 Gd1 166.10(8) . 3 ?
O2 Gd1 Gd1 114.83(8) . 3 ?
O1 Gd1 Gd1 33.95(7) . 3 ?
O4 Gd1 Gd1 111.42(7) . 3 ?
O1 Gd1 Gd1 33.61(6) 3 3 ?
N2 Gd1 Gd1 90.99(8) . 3 ?
N1 Gd1 Gd1 89.85(8) . 3 ?
C7 N1 C8 115.3(4) . . ?
C7 N1 Gd1 122.9(3) . . ?
C8 N1 Gd1 120.0(3) . . ?
C11 N2 C10 115.2(4) . . ?
C11 N2 Gd1 122.8(3) . . ?
C10 N2 Gd1 120.7(3) . . ?
C1 O1 Gd1 124.6(2) . . ?
C1 O1 Gd1 123.0(2) . 3 ?
Gd1 O1 Gd1 112.44(11) . 3 ?
C14 O2 Gd1 135.9(3) . . ?
C16 O3 Gd1 136.6(3) . . ?
C19 O4 Gd1 135.2(3) . . ?
C21 O5 Gd1 137.0(3) . . ?

_refine_diff_density_max         1.666
_refine_diff_density_min         -1.150
_refine_diff_density_rms         0.100

####################################################################### 
# 
# 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 1839665'
_audit_update_record             
;
2018-07-04 deposited with the CCDC.
2018-07-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C46 H62 N4 O12 Tb2'
_chemical_formula_weight         1180.83

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'
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                   11.5027(7)
_cell_length_b                   14.4339(9)
_cell_length_c                   15.1008(10)
_cell_angle_alpha                90
_cell_angle_beta                 109.5100(10)
_cell_angle_gamma                90
_cell_volume                     2363.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4990
_cell_measurement_theta_min      2.35
_cell_measurement_theta_max      27.38

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.659
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    3.033
_shelx_estimated_absorpt_T_min   0.506
_shelx_estimated_absorpt_T_max   0.582
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5061
_exptl_absorpt_correction_T_max  0.5822
_exptl_absorpt_process_details   'SADABS (Bruker, 2011)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'APEX2 CCD detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13819
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.944
_diffrn_reflns_theta_max         27.459
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5300
_reflns_number_gt                4393
_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 SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0287P)²+0.2416P] 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         5300
_refine_ls_number_parameters     296
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0275
_refine_ls_wR_factor_ref         0.0634
_refine_ls_wR_factor_gt          0.0595
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2148(3) -0.0726(2) 0.0086(2) 0.0205(7) Uani 1 1 d . . . . .
C2 C 0.2735(3) -0.1409(2) 0.0750(2) 0.0216(7) Uani 1 1 d . . . . .
C3 C 0.3842(3) -0.1804(2) 0.0732(2) 0.0265(8) Uani 1 1 d . . . . .
H3 H 0.419441 -0.227866 0.115268 0.032 Uiso 1 1 calc R U . . .
C4 C 0.4433(3) -0.1519(3) 0.0115(2) 0.0280(8) Uani 1 1 d . . . . .
C5 C 0.3875(3) -0.0819(3) -0.0503(2) 0.0267(8) Uani 1 1 d . . . . .
H5 H 0.427439 -0.059107 -0.090128 0.032 Uiso 1 1 calc R U . . .
C6 C 0.2737(3) -0.0436(2) -0.0556(2) 0.0222(7) Uani 1 1 d . . . . .
C7 C 0.2247(3) -0.1755(2) 0.1463(2) 0.0228(7) Uani 1 1 d . . . . .
H7 H 0.255121 -0.232341 0.173102 0.027 Uiso 1 1 calc R U . . .
C8 C 0.1204(3) -0.1855(2) 0.2545(2) 0.0281(8) Uani 1 1 d . . . . .
H8A H 0.157872 -0.151004 0.312112 0.034 Uiso 1 1 calc R U . . .
H8B H 0.159278 -0.246017 0.262265 0.034 Uiso 1 1 calc R U . . .
C9 C -0.0162(3) -0.1978(2) 0.2390(2) 0.0279(8) Uani 1 1 d . . . . .
H9A H -0.055495 -0.222838 0.176497 0.033 Uiso 1 1 calc R U . . .
H9B H -0.025040 -0.243370 0.283553 0.033 Uiso 1 1 calc R U . . .
C10 C -0.0844(3) -0.1111(2) 0.2488(2) 0.0261(8) Uani 1 1 d . . . . .
H10A H -0.162116 -0.128794 0.256063 0.031 Uiso 1 1 calc R U . . .
H10B H -0.036203 -0.078820 0.305490 0.031 Uiso 1 1 calc R U . . .
C11 C -0.2218(3) -0.0233(2) 0.1306(2) 0.0239(7) Uani 1 1 d . . . . .
H11 H -0.277868 -0.052341 0.153801 0.029 Uiso 1 1 calc R U . . .
C12 C 0.5624(3) -0.1963(3) 0.0106(3) 0.0355(9) Uani 1 1 d . . . . .
H12A H 0.596453 -0.160472 -0.028429 0.053 Uiso 1 1 calc R U . . .
H12B H 0.546046 -0.258113 -0.013735 0.053 Uiso 1 1 calc R U . . .
H12C H 0.620225 -0.198243 0.073444 0.053 Uiso 1 1 calc R U . . .
C13 C 0.4965(3) 0.0277(3) 0.2705(3) 0.0294(8) Uani 1 1 d . . . . .
H13A H 0.503458 -0.025804 0.234769 0.044 Uiso 1 1 calc R U . . .
H13B H 0.551279 0.021257 0.333970 0.044 Uiso 1 1 calc R U . . .
H13C H 0.518074 0.082150 0.242932 0.044 Uiso 1 1 calc R U . . .
C14 C 0.3656(3) 0.0362(2) 0.2700(2) 0.0224(7) Uani 1 1 d . . . . .
C15 C 0.3438(3) 0.0389(2) 0.3566(2) 0.0271(8) Uani 1 1 d . . . . .
H15 H 0.411654 0.037692 0.411437 0.033 Uiso 1 1 calc R U . . .
C16 C 0.2266(3) 0.0433(2) 0.3650(2) 0.0232(7) Uani 1 1 d . . . . .
C17 C 0.2143(4) 0.0506(3) 0.4611(2) 0.0338(9) Uani 1 1 d . . . . .
H17A H 0.160809 0.002411 0.468589 0.051 Uiso 1 1 calc R U . . .
H17B H 0.180269 0.109856 0.467638 0.051 Uiso 1 1 calc R U . . .
H17C H 0.294126 0.044025 0.508231 0.051 Uiso 1 1 calc R U . . .
C18 C -0.1610(3) 0.2850(2) 0.1756(3) 0.0289(8) Uani 1 1 d . . . . .
H18A H -0.140572 0.279333 0.242393 0.043 Uiso 1 1 calc R U . . .
H18B H -0.239424 0.256352 0.144737 0.043 Uiso 1 1 calc R U . . .
H18C H -0.165113 0.349383 0.158795 0.043 Uiso 1 1 calc R U . . .
C19 C -0.0635(3) 0.2379(2) 0.1455(2) 0.0219(7) Uani 1 1 d . . . . .
C20 C -0.0041(3) 0.2864(2) 0.0940(3) 0.0287(8) Uani 1 1 d . . . . .
H20 H -0.024717 0.348485 0.081697 0.034 Uiso 1 1 calc R U . . .
C21 C 0.0841(3) 0.2497(2) 0.0589(2) 0.0217(7) Uani 1 1 d . . . . .
C22 C 0.1410(3) 0.3130(2) 0.0052(2) 0.0273(8) Uani 1 1 d . . . . .
H22A H 0.213253 0.284260 -0.000810 0.041 Uiso 1 1 calc R U . . .
H22B H 0.163469 0.370597 0.038384 0.041 Uiso 1 1 calc R U . . .
H22C H 0.082534 0.324539 -0.056113 0.041 Uiso 1 1 calc R U . . .
N1 N 0.1445(3) -0.13661(18) 0.17639(19) 0.0220(6) Uani 1 1 d . . . . .
N2 N -0.1096(3) -0.04720(18) 0.16848(19) 0.0213(6) Uani 1 1 d . . . . .
O1 O 0.1074(2) -0.03624(14) 0.00525(15) 0.0193(5) Uani 1 1 d . . . . .
O2 O 0.2830(2) 0.04212(15) 0.19070(16) 0.0231(5) Uani 1 1 d . . . . .
O3 O 0.1265(2) 0.04031(15) 0.29591(15) 0.0238(5) Uani 1 1 d . . . . .
O4 O -0.0413(2) 0.15374(15) 0.17056(15) 0.0224(5) Uani 1 1 d . . . . .
O5 O 0.1204(2) 0.16701(15) 0.06822(16) 0.0242(5) Uani 1 1 d . . . . .
Tb1 Tb 0.06855(2) 0.03240(2) 0.13256(2) 0.01663(6) Uani 1 1 d . . . . .
O6 O -0.0702(3) 0.1199(3) 0.3588(2) 0.0553(9) Uani 1 1 d . . . . .
H6 H -0.039299 0.094275 0.323541 0.083 Uiso 1 1 calc R U . . .
C23 C -0.1954(4) 0.0986(3) 0.3310(3) 0.0444(11) Uani 1 1 d . . . . .
H23A H -0.235908 0.121513 0.268598 0.067 Uiso 1 1 calc R U . . .
H23B H -0.230984 0.126950 0.373474 0.067 Uiso 1 1 calc R U . . .
H23C H -0.205569 0.032615 0.331837 0.067 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.327(4) . ?
C1 C2 1.408(4) . ?
C1 C6 1.419(4) . ?
C2 C3 1.403(5) . ?
C2 C7 1.459(4) . ?
C3 C4 1.386(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(5) . ?
C4 C12 1.517(5) . ?
C5 C6 1.398(5) . ?
C5 H5 0.9300 . ?
C6 C11 1.456(5) 3 ?
C7 N1 1.285(4) . ?
C7 H7 0.9300 . ?
C8 N1 1.478(4) . ?
C8 C9 1.520(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.510(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N2 1.474(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N2 1.272(4) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.508(5) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 O2 1.259(4) . ?
C14 C15 1.411(5) . ?
C15 C16 1.397(5) . ?
C15 H15 0.9300 . ?
C16 O3 1.270(4) . ?
C16 C17 1.508(5) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.506(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 O4 1.273(4) . ?
C19 C20 1.383(4) . ?
C20 C21 1.396(5) . ?
C20 H20 0.9300 . ?
C21 O5 1.256(4) . ?
C21 C22 1.509(4) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
N1 Tb1 2.601(3) . ?
N2 Tb1 2.560(3) . ?
O1 Tb1 2.335(2) . ?
O1 Tb1 2.370(2) 3 ?
O2 Tb1 2.330(2) . ?
O3 Tb1 2.333(2) . ?
O4 Tb1 2.341(2) . ?
O5 Tb1 2.337(2) . ?
Tb1 Tb1 3.8952(4) 3 ?
O6 C23 1.393(4) . ?
O6 H6 0.8200 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 121.5(3) . . ?
O1 C1 C6 120.6(3) . . ?
C2 C1 C6 117.9(3) . . ?
C3 C2 C1 119.6(3) . . ?
C3 C2 C7 116.8(3) . . ?
C1 C2 C7 123.6(3) . . ?
C4 C3 C2 122.9(3) . . ?
C4 C3 H3 118.5 . . ?
C2 C3 H3 118.5 . . ?
C5 C4 C3 116.8(3) . . ?
C5 C4 C12 121.3(3) . . ?
C3 C4 C12 121.9(3) . . ?
C4 C5 C6 122.9(3) . . ?
C4 C5 H5 118.6 . . ?
C6 C5 H5 118.6 . . ?
C5 C6 C1 119.8(3) . . ?
C5 C6 C11 116.1(3) . 3 ?
C1 C6 C11 124.1(3) . 3 ?
N1 C7 C2 127.6(3) . . ?
N1 C7 H7 116.2 . . ?
C2 C7 H7 116.2 . . ?
N1 C8 C9 113.1(3) . . ?
N1 C8 H8A 108.9 . . ?
C9 C8 H8A 108.9 . . ?
N1 C8 H8B 108.9 . . ?
C9 C8 H8B 108.9 . . ?
H8A C8 H8B 107.8 . . ?
C10 C9 C8 115.6(3) . . ?
C10 C9 H9A 108.4 . . ?
C8 C9 H9A 108.4 . . ?
C10 C9 H9B 108.4 . . ?
C8 C9 H9B 108.4 . . ?
H9A C9 H9B 107.4 . . ?
N2 C10 C9 113.8(3) . . ?
N2 C10 H10A 108.8 . . ?
C9 C10 H10A 108.8 . . ?
N2 C10 H10B 108.8 . . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
N2 C11 C6 128.3(3) . 3 ?
N2 C11 H11 115.8 . . ?
C6 C11 H11 115.8 3 . ?
C4 C12 H12A 109.5 . . ?
C4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C14 C15 124.6(3) . . ?
O2 C14 C13 116.4(3) . . ?
C15 C14 C13 119.0(3) . . ?
C16 C15 C14 124.2(3) . . ?
C16 C15 H15 117.9 . . ?
C14 C15 H15 117.9 . . ?
O3 C16 C15 124.1(3) . . ?
O3 C16 C17 116.3(3) . . ?
C15 C16 C17 119.6(3) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C19 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O4 C19 C20 124.2(3) . . ?
O4 C19 C18 115.9(3) . . ?
C20 C19 C18 119.9(3) . . ?
C19 C20 C21 125.4(3) . . ?
C19 C20 H20 117.3 . . ?
C21 C20 H20 117.3 . . ?
O5 C21 C20 125.1(3) . . ?
O5 C21 C22 116.6(3) . . ?
C20 C21 C22 118.3(3) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C7 N1 C8 114.9(3) . . ?
C7 N1 Tb1 122.6(2) . . ?
C8 N1 Tb1 120.9(2) . . ?
C11 N2 C10 115.5(3) . . ?
C11 N2 Tb1 123.1(2) . . ?
C10 N2 Tb1 120.3(2) . . ?
C1 O1 Tb1 124.61(19) . . ?
C1 O1 Tb1 123.61(19) . 3 ?
Tb1 O1 Tb1 111.77(8) . 3 ?
C14 O2 Tb1 136.2(2) . . ?
C16 O3 Tb1 136.9(2) . . ?
C19 O4 Tb1 135.4(2) . . ?
C21 O5 Tb1 135.6(2) . . ?
O2 Tb1 O3 72.90(8) . . ?
O2 Tb1 O1 82.30(7) . . ?
O3 Tb1 O1 145.65(8) . . ?
O2 Tb1 O5 73.82(8) . . ?
O3 Tb1 O5 112.11(8) . . ?
O1 Tb1 O5 82.23(7) . . ?
O2 Tb1 O4 116.94(8) . . ?
O3 Tb1 O4 72.01(8) . . ?
O1 Tb1 O4 141.90(7) . . ?
O5 Tb1 O4 73.36(8) . . ?
O2 Tb1 O1 144.65(7) . 3 ?
O3 Tb1 O1 141.80(8) . 3 ?
O1 Tb1 O1 68.23(8) . 3 ?
O5 Tb1 O1 82.95(8) . 3 ?
O4 Tb1 O1 79.93(7) . 3 ?
O2 Tb1 N2 140.24(8) . . ?
O3 Tb1 N2 76.36(8) . . ?
O1 Tb1 N2 111.77(8) . . ?
O5 Tb1 N2 142.62(8) . . ?
O4 Tb1 N2 75.40(8) . . ?
O1 Tb1 N2 71.78(8) 3 . ?
O2 Tb1 N1 74.76(8) . . ?
O3 Tb1 N1 79.85(8) . . ?
O1 Tb1 N1 70.80(8) . . ?
O5 Tb1 N1 140.77(8) . . ?
O4 Tb1 N1 143.36(8) . . ?
O1 Tb1 N1 111.17(8) 3 . ?
N2 Tb1 N1 75.52(9) . . ?
O2 Tb1 Tb1 114.58(5) . 3 ?
O3 Tb1 Tb1 166.66(6) . 3 ?
O1 Tb1 Tb1 34.40(5) . 3 ?
O5 Tb1 Tb1 81.04(6) . 3 ?
O4 Tb1 Tb1 111.42(5) . 3 ?
O1 Tb1 Tb1 33.82(5) 3 3 ?
N2 Tb1 Tb1 91.84(6) . 3 ?
N1 Tb1 Tb1 91.30(6) . 3 ?
C23 O6 H6 109.5 . . ?
O6 C23 H23A 109.5 . . ?
O6 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O6 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

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
C10 H10B O3 0.97 2.58 3.165(4) 118.9 . yes
O6 H6 O3 0.82 2.22 2.962(4) 149.8 . yes
O6 H6 O4 0.82 2.46 3.009(4) 125.6 . yes

_refine_diff_density_max         0.806
_refine_diff_density_min         -0.619
_refine_diff_density_rms         0.105

####################################################################### 
# 
# 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 1839667'
_audit_update_record             
;
2018-04-26 deposited with the CCDC.
2018-07-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H54 Er2 N4 O10'
_chemical_formula_weight         1133.43

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'
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                   11.664(3)
_cell_length_b                   14.533(4)
_cell_length_c                   15.322(4)
_cell_angle_alpha                90
_cell_angle_beta                 109.608(3)
_cell_angle_gamma                90
_cell_volume                     2446.6(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6140
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      27.69

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.539
_exptl_crystal_F_000             1124
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    3.461
_shelx_estimated_absorpt_T_min   0.466
_shelx_estimated_absorpt_T_max   0.516
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4664
_exptl_absorpt_correction_T_max  0.5164
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13199
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.324
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4969
_reflns_number_gt                4022
_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 SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0653P)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         4969
_refine_ls_number_parameters     276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0480
_refine_ls_R_factor_gt           0.0395
_refine_ls_wR_factor_ref         0.1016
_refine_ls_wR_factor_gt          0.0966
_refine_ls_goodness_of_fit_ref   0.984
_refine_ls_restrained_S_all      0.984
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2108(4) -0.0715(3) 0.0090(3) 0.0436(10) Uani 1 1 d . . . . .
C2 C 0.2686(4) -0.1398(3) 0.0753(3) 0.0511(11) Uani 1 1 d . . . . .
C3 C 0.3787(4) -0.1793(3) 0.0733(4) 0.0595(13) Uani 1 1 d . . . . .
H3 H 0.413522 -0.226485 0.114740 0.071 Uiso 1 1 calc R U . . .
C4 C 0.4370(5) -0.1513(4) 0.0127(4) 0.0652(15) Uani 1 1 d . . . . .
C5 C 0.3815(4) -0.0817(4) -0.0483(4) 0.0635(14) Uani 1 1 d . . . . .
H5 H 0.421428 -0.059249 -0.087166 0.076 Uiso 1 1 calc R U . . .
C6 C 0.2695(4) -0.0430(3) -0.0551(4) 0.0491(11) Uani 1 1 d . . . . .
C7 C 0.2209(5) -0.1732(3) 0.1450(3) 0.0549(12) Uani 1 1 d . . . . .
H7 H 0.250501 -0.229679 0.171542 0.066 Uiso 1 1 calc R U . . .
C8 C 0.1181(5) -0.1825(4) 0.2517(4) 0.0653(14) Uani 1 1 d . . . . .
H8A H 0.154244 -0.147487 0.308238 0.078 Uiso 1 1 calc R U . . .
H8B H 0.157713 -0.242103 0.260333 0.078 Uiso 1 1 calc R U . . .
C9 C -0.0160(5) -0.1966(4) 0.2372(4) 0.0679(15) Uani 1 1 d . . . . .
H9A H -0.054834 -0.222385 0.175933 0.081 Uiso 1 1 calc R U . . .
H9B H -0.023415 -0.241279 0.281961 0.081 Uiso 1 1 calc R U . . .
C10 C -0.0832(5) -0.1111(4) 0.2459(4) 0.0623(14) Uani 1 1 d . . . . .
H10A H -0.160276 -0.128570 0.252179 0.075 Uiso 1 1 calc R U . . .
H10B H -0.036293 -0.079028 0.302093 0.075 Uiso 1 1 calc R U . . .
C11 C -0.2172(5) -0.0222(3) 0.1283(4) 0.0576(13) Uani 1 1 d . . . . .
H11 H -0.272691 -0.050708 0.151140 0.069 Uiso 1 1 calc R U . . .
C12 C 0.5535(5) -0.1949(5) 0.0107(5) 0.089(2) Uani 1 1 d . . . . .
H12A H 0.596514 -0.152097 -0.014742 0.134 Uiso 1 1 calc R U . . .
H12B H 0.534817 -0.249289 -0.027001 0.134 Uiso 1 1 calc R U . . .
H12C H 0.603381 -0.211021 0.072573 0.134 Uiso 1 1 calc R U . . .
C13 C 0.4894(5) 0.0291(4) 0.2644(5) 0.0786(19) Uani 1 1 d . . . . .
H13A H 0.496578 -0.024730 0.230317 0.118 Uiso 1 1 calc R U . . .
H13B H 0.543756 0.024024 0.327137 0.118 Uiso 1 1 calc R U . . .
H13C H 0.509903 0.082638 0.236098 0.118 Uiso 1 1 calc R U . . .
C14 C 0.3584(5) 0.0376(3) 0.2641(4) 0.0535(13) Uani 1 1 d . . . . .
C15 C 0.3392(5) 0.0408(4) 0.3474(4) 0.0618(14) Uani 1 1 d . . . . .
H15 H 0.407094 0.040306 0.400964 0.074 Uiso 1 1 calc R U . . .
C16 C 0.2232(5) 0.0448(3) 0.3575(4) 0.0530(12) Uani 1 1 d . . . . .
C17 C 0.2128(6) 0.0523(4) 0.4526(4) 0.0750(17) Uani 1 1 d . . . . .
H17A H 0.146843 0.014406 0.455699 0.112 Uiso 1 1 calc R U . . .
H17B H 0.197602 0.115124 0.464551 0.112 Uiso 1 1 calc R U . . .
H17C H 0.287321 0.031998 0.498066 0.112 Uiso 1 1 calc R U . . .
C18 C -0.1573(5) 0.2843(4) 0.1731(4) 0.0706(15) Uani 1 1 d . . . . .
H18A H -0.132975 0.284934 0.239539 0.106 Uiso 1 1 calc R U . . .
H18B H -0.233336 0.252258 0.148110 0.106 Uiso 1 1 calc R U . . .
H18C H -0.166602 0.346311 0.150339 0.106 Uiso 1 1 calc R U . . .
C19 C -0.0607(4) 0.2356(3) 0.1438(4) 0.0520(11) Uani 1 1 d . . . . .
C20 C -0.0012(5) 0.2838(3) 0.0939(4) 0.0628(14) Uani 1 1 d . . . . .
H20 H -0.020125 0.345740 0.082312 0.075 Uiso 1 1 calc R U . . .
C21 C 0.0858(4) 0.2455(3) 0.0596(3) 0.0492(11) Uani 1 1 d . . . . .
C22 C 0.1460(5) 0.3075(3) 0.0082(4) 0.0622(13) Uani 1 1 d . . . . .
H22A H 0.216943 0.277576 0.003351 0.093 Uiso 1 1 calc R U . . .
H22B H 0.169203 0.364278 0.041489 0.093 Uiso 1 1 calc R U . . .
H22C H 0.089870 0.319882 -0.052662 0.093 Uiso 1 1 calc R U . . .
Er1 Er 0.06643(2) 0.03167(2) 0.13021(2) 0.04038(10) Uani 1 1 d . . . . .
N1 N 0.1426(4) -0.1342(3) 0.1747(3) 0.0522(9) Uani 1 1 d . . . . .
N2 N -0.1069(4) -0.0472(3) 0.1668(3) 0.0508(10) Uani 1 1 d . . . . .
O1 O 0.1048(3) -0.03532(19) 0.0057(2) 0.0442(7) Uani 1 1 d . . . . .
O2 O 0.2765(3) 0.0408(2) 0.1847(3) 0.0540(8) Uani 1 1 d . . . . .
O3 O 0.1245(3) 0.0405(2) 0.2898(2) 0.0543(9) Uani 1 1 d . . . . .
O4 O -0.0416(3) 0.1516(2) 0.1668(2) 0.0508(8) Uani 1 1 d . . . . .
O5 O 0.1172(3) 0.1627(2) 0.0676(2) 0.0548(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.329(5) . ?
C1 C2 1.419(7) . ?
C1 C6 1.434(7) . ?
C2 C3 1.416(6) . ?
C2 C7 1.444(7) . ?
C3 C4 1.382(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(8) . ?
C4 C12 1.510(8) . ?
C5 C6 1.393(7) . ?
C5 H5 0.9300 . ?
C6 C11 1.439(7) 3 ?
C7 N1 1.280(6) . ?
C7 H7 0.9300 . ?
C8 N1 1.481(6) . ?
C8 C9 1.517(8) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.499(8) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N2 1.477(6) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 N2 1.275(6) . ?
C11 H11 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C13 C14 1.531(8) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 O2 1.271(6) . ?
C14 C15 1.368(8) . ?
C15 C16 1.414(8) . ?
C15 H15 0.9300 . ?
C16 O3 1.267(6) . ?
C16 C17 1.505(8) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 C19 1.521(7) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 O4 1.270(5) . ?
C19 C20 1.382(7) . ?
C20 C21 1.406(7) . ?
C20 H20 0.9300 . ?
C21 O5 1.253(5) . ?
C21 C22 1.514(6) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
Er1 O5 2.297(3) . ?
Er1 O3 2.311(3) . ?
Er1 O2 2.312(3) . ?
Er1 O1 2.315(3) . ?
Er1 O4 2.326(3) . ?
Er1 O1 2.353(3) 3 ?
Er1 N2 2.545(4) . ?
Er1 N1 2.581(4) . ?
Er1 Er1 3.8756(10) 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 C1 C2 121.1(4) . . ?
O1 C1 C6 120.8(4) . . ?
C2 C1 C6 118.1(4) . . ?
C3 C2 C1 119.0(5) . . ?
C3 C2 C7 117.3(4) . . ?
C1 C2 C7 123.7(4) . . ?
C4 C3 C2 123.3(5) . . ?
C4 C3 H3 118.4 . . ?
C2 C3 H3 118.4 . . ?
C5 C4 C3 116.5(5) . . ?
C5 C4 C12 120.9(6) . . ?
C3 C4 C12 122.6(6) . . ?
C4 C5 C6 124.1(5) . . ?
C4 C5 H5 118.0 . . ?
C6 C5 H5 118.0 . . ?
C5 C6 C1 118.9(5) . . ?
C5 C6 C11 117.8(5) . 3 ?
C1 C6 C11 123.3(4) . 3 ?
N1 C7 C2 127.8(4) . . ?
N1 C7 H7 116.1 . . ?
C2 C7 H7 116.1 . . ?
N1 C8 C9 114.3(4) . . ?
N1 C8 H8A 108.7 . . ?
C9 C8 H8A 108.7 . . ?
N1 C8 H8B 108.7 . . ?
C9 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C10 C9 C8 114.8(5) . . ?
C10 C9 H9A 108.6 . . ?
C8 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
C8 C9 H9B 108.6 . . ?
H9A C9 H9B 107.6 . . ?
N2 C10 C9 114.0(4) . . ?
N2 C10 H10A 108.7 . . ?
C9 C10 H10A 108.7 . . ?
N2 C10 H10B 108.7 . . ?
C9 C10 H10B 108.7 . . ?
H10A C10 H10B 107.6 . . ?
N2 C11 C6 130.3(5) . 3 ?
N2 C11 H11 114.9 . . ?
C6 C11 H11 114.9 3 . ?
C4 C12 H12A 109.5 . . ?
C4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C14 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O2 C14 C15 125.9(5) . . ?
O2 C14 C13 115.8(5) . . ?
C15 C14 C13 118.3(5) . . ?
C14 C15 C16 124.5(5) . . ?
C14 C15 H15 117.8 . . ?
C16 C15 H15 117.8 . . ?
O3 C16 C15 123.2(5) . . ?
O3 C16 C17 116.8(5) . . ?
C15 C16 C17 120.0(5) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C19 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O4 C19 C20 124.5(5) . . ?
O4 C19 C18 116.3(5) . . ?
C20 C19 C18 119.2(4) . . ?
C19 C20 C21 124.5(4) . . ?
C19 C20 H20 117.8 . . ?
C21 C20 H20 117.8 . . ?
O5 C21 C20 124.6(4) . . ?
O5 C21 C22 116.9(4) . . ?
C20 C21 C22 118.6(4) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O5 Er1 O3 111.75(12) . . ?
O5 Er1 O2 73.30(11) . . ?
O3 Er1 O2 73.52(13) . . ?
O5 Er1 O1 81.74(11) . . ?
O3 Er1 O1 145.70(11) . . ?
O2 Er1 O1 81.20(12) . . ?
O5 Er1 O4 73.51(12) . . ?
O3 Er1 O4 72.15(11) . . ?
O2 Er1 O4 117.66(12) . . ?
O1 Er1 O4 141.59(11) . . ?
O5 Er1 O1 82.69(11) . 3 ?
O3 Er1 O1 142.71(12) . 3 ?
O2 Er1 O1 143.11(12) . 3 ?
O1 Er1 O1 67.74(12) . 3 ?
O4 Er1 O1 80.16(11) . 3 ?
O5 Er1 N2 143.19(12) . . ?
O3 Er1 N2 76.37(13) . . ?
O2 Er1 N2 140.39(13) . . ?
O1 Er1 N2 112.30(12) . . ?
O4 Er1 N2 75.52(12) . . ?
O1 Er1 N2 72.81(12) 3 . ?
O5 Er1 N1 140.39(12) . . ?
O3 Er1 N1 79.63(12) . . ?
O2 Er1 N1 74.29(12) . . ?
O1 Er1 N1 71.34(11) . . ?
O4 Er1 N1 143.36(12) . . ?
O1 Er1 N1 111.68(11) 3 . ?
N2 Er1 N1 75.48(13) . . ?
O5 Er1 Er1 80.61(9) . 3 ?
O3 Er1 Er1 167.51(8) . 3 ?
O2 Er1 Er1 113.22(9) . 3 ?
O1 Er1 Er1 34.19(8) . 3 ?
O4 Er1 Er1 111.35(8) . 3 ?
O1 Er1 Er1 33.55(7) 3 3 ?
N2 Er1 Er1 92.70(10) . 3 ?
N1 Er1 Er1 91.90(9) . 3 ?
C7 N1 C8 115.1(4) . . ?
C7 N1 Er1 122.9(3) . . ?
C8 N1 Er1 120.8(3) . . ?
C11 N2 C10 116.2(4) . . ?
C11 N2 Er1 121.5(3) . . ?
C10 N2 Er1 121.3(3) . . ?
C1 O1 Er1 124.7(3) . . ?
C1 O1 Er1 123.0(3) . 3 ?
Er1 O1 Er1 112.25(12) . 3 ?
C14 O2 Er1 135.1(3) . . ?
C16 O3 Er1 137.1(4) . . ?
C19 O4 Er1 135.4(3) . . ?
C21 O5 Er1 136.9(3) . . ?

_refine_diff_density_max         2.074
_refine_diff_density_min         -1.755
_refine_diff_density_rms         0.134

