# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_Dy_Complex
_database_code_depnum_ccdc_archive 'CCDC 2081829'
loop_
_audit_author_name
_audit_author_address
'Alexandros Kitos'
;Department of Chemistry and Biomolecular Sciences, University of Ottawa, Ottawa, Canada
Canada
;
_audit_update_record             
;
2021-05-04 deposited with the CCDC.	2021-07-07 downloaded from the CCDC.
;
#=============================================================
# CHEMICAL DATA

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H27 Dy N4 O6'
_chemical_formula_sum            'C20 H27 Dy N4 O6'
_chemical_formula_weight         581.95

#=============================================================
# CRYSTAL DATA

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'
Dy Dy -0.1892 4.4098 '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/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   9.8270(9)
_cell_length_b                   12.6308(10)
_cell_length_c                   19.5062(18)
_cell_angle_alpha                90
_cell_angle_beta                 100.309(3)
_cell_angle_gamma                90
_cell_volume                     2382.1(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    9912
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      28.29

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_F_000             1156
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    3.177
_shelx_estimated_absorpt_T_min   0.665
_shelx_estimated_absorpt_T_max   0.785
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6327
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?

#=============================================================
# EXPERIMENTAL DATA

_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_method       'ω and φ scans'
_diffrn_ambient_temperature      200(2)
_diffrn_reflns_number            39480
_diffrn_reflns_av_unetI/netI     0.0382
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.930
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000

#=============================================================
# REFINEMENT DATA 

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

_reflns_number_total             4676
_reflns_number_gt                3814
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4676
_refine_ls_number_parameters     295
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0300
_refine_ls_wR_factor_ref         0.0697
_refine_ls_wR_factor_gt          0.0633
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0272P)²+3.7304P] where P=(Fo²+2Fc²)/3'
_refine_diff_density_max         1.533
_refine_diff_density_min         -0.771
_refine_diff_density_rms         0.115

#=============================================================
# GENERAL COMPUTING 

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#=============================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
Dy Dy 0.45751(2) 0.64965(2) 0.29610(2) 0.02286(7) Uani 1 1 d . . . . .
C1 C 0.2769(5) 0.4298(3) 0.1094(2) 0.0421(12) Uani 1 1 d . . . . .
H1A H 0.368049 0.399860 0.107226 0.063 Uiso 1 1 calc R U . . .
H1B H 0.227417 0.443954 0.062036 0.063 Uiso 1 1 calc R U . . .
H1C H 0.223878 0.379423 0.132299 0.063 Uiso 1 1 calc R U . . .
C2 C 0.2944(4) 0.5314(3) 0.1501(2) 0.0269(9) Uani 1 1 d . . . . .
C3 C 0.2163(5) 0.6190(3) 0.1241(2) 0.0300(10) Uani 1 1 d . . . . .
H3 H 0.157181 0.611585 0.080196 0.036 Uiso 1 1 calc R U . . .
C4 C 0.2178(4) 0.7179(3) 0.1577(2) 0.0261(9) Uani 1 1 d . . . . .
C5 C 0.1242(5) 0.8027(4) 0.1216(3) 0.0400(12) Uani 1 1 d . . . . .
H5A H 0.034711 0.799483 0.137076 0.060 Uiso 1 1 calc R U . . .
H5B H 0.110350 0.791743 0.071093 0.060 Uiso 1 1 calc R U . . .
H5C H 0.166348 0.872279 0.133071 0.060 Uiso 1 1 calc R U . . .
C6 C 0.0513(5) 0.5803(4) 0.3840(3) 0.0481(13) Uani 1 1 d . . . . .
H6A H 0.048549 0.512185 0.359766 0.072 Uiso 1 1 calc R U . . .
H6B H -0.032546 0.620691 0.365824 0.072 Uiso 1 1 calc R U . . .
H6C H 0.056522 0.568042 0.434018 0.072 Uiso 1 1 calc R U . . .
C7 C 0.1769(5) 0.6421(3) 0.3723(2) 0.0332(10) Uani 1 1 d . . . . .
C8 C 0.2009(5) 0.7412(4) 0.4047(2) 0.0415(12) Uani 1 1 d . . . . .
H8 H 0.135017 0.765887 0.431200 0.050 Uiso 1 1 calc R U . . .
C9 C 0.3134(5) 0.8061(3) 0.4010(2) 0.0359(11) Uani 1 1 d . . . . .
C10 C 0.3324(6) 0.9064(4) 0.4438(3) 0.0560(16) Uani 1 1 d . . . . .
H10A H 0.400292 0.894142 0.486350 0.084 Uiso 1 1 calc R U . . .
H10B H 0.243854 0.927243 0.456146 0.084 Uiso 1 1 calc R U . . .
H10C H 0.365534 0.963060 0.416563 0.084 Uiso 1 1 calc R U . . .
C11 C 0.5354(5) 0.3430(3) 0.4286(2) 0.0371(11) Uani 1 1 d . . . . .
H11A H 0.436000 0.334949 0.428066 0.056 Uiso 1 1 calc R U . . .
H11B H 0.586474 0.328510 0.475558 0.056 Uiso 1 1 calc R U . . .
H11C H 0.564425 0.293036 0.395571 0.056 Uiso 1 1 calc R U . . .
C12 C 0.5649(4) 0.4545(3) 0.4079(2) 0.0281(9) Uani 1 1 d . . . . .
C13 C 0.6561(5) 0.5164(3) 0.4541(2) 0.0367(11) Uani 1 1 d . . . . .
H13 H 0.696046 0.486293 0.497714 0.044 Uiso 1 1 calc R U . . .
C14 C 0.6925(4) 0.6203(3) 0.4402(2) 0.0289(10) Uani 1 1 d . . . . .
C15 C 0.7935(5) 0.6788(4) 0.4948(2) 0.0431(12) Uani 1 1 d . . . . .
H15A H 0.870852 0.704957 0.474026 0.065 Uiso 1 1 calc R U . . .
H15B H 0.828658 0.630733 0.533337 0.065 Uiso 1 1 calc R U . . .
H15C H 0.746604 0.738768 0.512412 0.065 Uiso 1 1 calc R U . . .
C16 C 0.7208(5) 0.4929(3) 0.2419(2) 0.0322(10) Uani 1 1 d . . . . .
H16 H 0.666755 0.436261 0.254642 0.039 Uiso 1 1 calc R U . . .
C17 C 0.8435(5) 0.4704(4) 0.2205(2) 0.0394(12) Uani 1 1 d . . . . .
H17 H 0.876138 0.399758 0.219226 0.047 Uiso 1 1 calc R U . . .
C18 C 0.9162(6) 0.5535(4) 0.2012(3) 0.0494(14) Uani 1 1 d . . . . .
H18 H 1.000797 0.539500 0.185737 0.059 Uiso 1 1 calc R U . . .
C19 C 0.7544(4) 0.6678(3) 0.2248(2) 0.0271(9) Uani 1 1 d . . . . .
C20 C 0.7002(4) 0.7786(3) 0.2271(2) 0.0263(9) Uani 1 1 d . . . . .
N1 N 0.6751(4) 0.5928(3) 0.24525(17) 0.0267(8) Uani 1 1 d . . . . .
N2 N 0.5857(4) 0.7902(3) 0.24845(19) 0.0278(8) Uani 1 1 d D . . . .
H2A H 0.563(5) 0.8557(13) 0.248(3) 0.042 Uiso 1 1 d D U . . .
N3 N 0.7799(4) 0.8549(3) 0.2060(2) 0.0401(10) Uani 1 1 d D . . . .
H3A H 0.746(5) 0.9173(19) 0.199(3) 0.060 Uiso 1 1 d D U . . .
H3B H 0.854(3) 0.836(4) 0.192(3) 0.060 Uiso 1 1 d D U . . .
N4 N 0.8737(4) 0.6548(3) 0.2031(2) 0.0432(10) Uani 1 1 d . . . . .
O1 O 0.3788(3) 0.5297(2) 0.20768(14) 0.0289(7) Uani 1 1 d . . . . .
O2 O 0.2920(3) 0.7401(2) 0.21507(15) 0.0293(7) Uani 1 1 d . . . . .
O3 O 0.2536(3) 0.5993(2) 0.33526(16) 0.0343(7) Uani 1 1 d . . . . .
O4 O 0.4024(3) 0.7879(2) 0.36389(16) 0.0374(8) Uani 1 1 d . . . . .
O5 O 0.5035(3) 0.4849(2) 0.34851(15) 0.0314(7) Uani 1 1 d . . . . .
O6 O 0.6469(3) 0.6705(2) 0.38582(16) 0.0366(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
Dy O4 2.313(3) . ?
Dy O1 2.322(3) . ?
Dy O5 2.327(3) . ?
Dy O6 2.331(3) . ?
Dy O2 2.351(3) . ?
Dy O3 2.357(3) . ?
Dy N2 2.453(3) . ?
Dy N1 2.614(3) . ?
C1 C2 1.503(6) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 O1 1.271(5) . ?
C2 C3 1.389(6) . ?
C3 C4 1.410(6) . ?
C3 H3 0.9500 . ?
C4 O2 1.252(5) . ?
C4 C5 1.504(6) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.512(6) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 O3 1.256(5) . ?
C7 C8 1.404(6) . ?
C8 C9 1.389(7) . ?
C8 H8 0.9500 . ?
C9 O4 1.252(5) . ?
C9 C10 1.511(6) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.507(5) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 O5 1.267(5) . ?
C12 C13 1.392(6) . ?
C13 C14 1.400(6) . ?
C13 H13 0.9500 . ?
C14 O6 1.248(5) . ?
C14 C15 1.512(6) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 N1 1.345(5) . ?
C16 C17 1.374(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.360(7) . ?
C17 H17 0.9500 . ?
C18 N4 1.350(6) . ?
C18 H18 0.9500 . ?
C19 N4 1.326(6) . ?
C19 N1 1.332(5) . ?
C19 C20 1.501(5) . ?
C20 N2 1.276(5) . ?
C20 N3 1.351(5) . ?
N2 H2A 0.858(10) . ?
N3 H3A 0.857(10) . ?
N3 H3B 0.857(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
O4 Dy O1 146.77(11) . . ?
O4 Dy O5 118.10(11) . . ?
O1 Dy O5 75.84(9) . . ?
O4 Dy O6 73.90(11) . . ?
O1 Dy O6 138.30(10) . . ?
O5 Dy O6 72.83(10) . . ?
O4 Dy O2 79.22(11) . . ?
O1 Dy O2 73.70(9) . . ?
O5 Dy O2 141.85(10) . . ?
O6 Dy O2 144.44(9) . . ?
O4 Dy O3 73.67(10) . . ?
O1 Dy O3 82.81(10) . . ?
O5 Dy O3 74.07(11) . . ?
O6 Dy O3 113.48(11) . . ?
O2 Dy O3 79.81(10) . . ?
O4 Dy N2 81.90(11) . . ?
O1 Dy N2 108.43(11) . . ?
O5 Dy N2 137.81(11) . . ?
O6 Dy N2 78.91(11) . . ?
O2 Dy N2 74.58(11) . . ?
O3 Dy N2 147.38(11) . . ?
O4 Dy N1 135.70(11) . . ?
O1 Dy N1 74.06(10) . . ?
O5 Dy N1 79.25(10) . . ?
O6 Dy N1 73.63(11) . . ?
O2 Dy N1 113.13(10) . . ?
O3 Dy N1 148.20(10) . . ?
N2 Dy N1 62.90(11) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 124.5(4) . . ?
O1 C2 C1 116.6(4) . . ?
C3 C2 C1 118.9(4) . . ?
C2 C3 C4 125.2(4) . . ?
C2 C3 H3 117.4 . . ?
C4 C3 H3 117.4 . . ?
O2 C4 C3 124.7(4) . . ?
O2 C4 C5 117.9(4) . . ?
C3 C4 C5 117.3(4) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 H6A 109.5 . . ?
C7 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C7 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O3 C7 C8 125.0(4) . . ?
O3 C7 C6 117.0(4) . . ?
C8 C7 C6 117.9(4) . . ?
C9 C8 C7 125.0(4) . . ?
C9 C8 H8 117.5 . . ?
C7 C8 H8 117.5 . . ?
O4 C9 C8 124.6(4) . . ?
O4 C9 C10 116.3(4) . . ?
C8 C9 C10 119.2(4) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C12 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O5 C12 C13 124.6(4) . . ?
O5 C12 C11 116.4(4) . . ?
C13 C12 C11 119.0(4) . . ?
C12 C13 C14 124.0(4) . . ?
C12 C13 H13 118.0 . . ?
C14 C13 H13 118.0 . . ?
O6 C14 C13 125.1(4) . . ?
O6 C14 C15 116.2(4) . . ?
C13 C14 C15 118.7(4) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 C17 121.8(4) . . ?
N1 C16 H16 119.1 . . ?
C17 C16 H16 119.1 . . ?
C18 C17 C16 117.3(4) . . ?
C18 C17 H17 121.4 . . ?
C16 C17 H17 121.4 . . ?
N4 C18 C17 122.9(4) . . ?
N4 C18 H18 118.5 . . ?
C17 C18 H18 118.5 . . ?
N4 C19 N1 127.3(4) . . ?
N4 C19 C20 117.6(4) . . ?
N1 C19 C20 115.1(4) . . ?
N2 C20 N3 127.7(4) . . ?
N2 C20 C19 117.0(4) . . ?
N3 C20 C19 115.3(4) . . ?
C19 N1 C16 115.8(4) . . ?
C19 N1 Dy 118.7(3) . . ?
C16 N1 Dy 125.4(3) . . ?
C20 N2 Dy 125.7(3) . . ?
C20 N2 H2A 111(3) . . ?
Dy N2 H2A 123(3) . . ?
C20 N3 H3A 118(4) . . ?
C20 N3 H3B 118(4) . . ?
H3A N3 H3B 122(5) . . ?
C19 N4 C18 114.9(4) . . ?
C2 O1 Dy 136.3(2) . . ?
C4 O2 Dy 135.5(2) . . ?
C7 O3 Dy 134.6(3) . . ?
C9 O4 Dy 136.7(3) . . ?
C12 O5 Dy 134.1(3) . . ?
C14 O6 Dy 134.3(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1A O4 0.98 2.64 3.582(6) 162.1 2_645 yes
C16 H16 O2 0.95 2.56 3.310(5) 135.7 2_645 yes



_exptl_crystal_preparation       'Magnetic properties,Luminescent'
