# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2022

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 2129444'
loop_
_audit_author_name
_audit_author_address
'Francielli Sousa Santana'
;Universidade Federal do Parana
Brazil
;
_audit_update_record             
;
2021-12-17 deposited with the CCDC.	2022-04-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_structural     '[DyC29H30ClN4O2]'
_chemical_formula_moiety         'C29 H30 Cl Dy N4 O2'
_chemical_formula_sum            'C29 H30 Cl Dy N4 O2'
_chemical_formula_weight         664.52

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Dy Dy -0.1892 4.4098 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   17.6920(8)
_cell_length_b                   10.2893(5)
_cell_length_c                   15.0931(6)
_cell_angle_alpha                90
_cell_angle_beta                 103.871(2)
_cell_angle_gamma                90
_cell_volume                     2667.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9965
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      27.68
_exptl_crystal_description       rhomb
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.061
_exptl_crystal_size_mid          0.131
_exptl_crystal_size_max          0.152
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.655
_exptl_crystal_F_000             1324
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    2.935
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6753
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   
;
SADABS-2012/1 - Bruker AXS area detector scaling and absorption correction 
;
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 Venture/Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            66286
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_av_R_equivalents  0.0508
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.837
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3062
_reflns_number_gt                2866
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2015 (Sheldrick 2015a)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015b)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976 and Farrugia, 2012)'
_computing_publication_material  
'SHELXL-2014/7 (Sheldrick, 2015) and WINGX (Farrugia, 2012)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0283P)²+12.1752P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3062
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0326
_refine_ls_R_factor_gt           0.0288
_refine_ls_wR_factor_ref         0.0710
_refine_ls_wR_factor_gt          0.0697
_refine_ls_goodness_of_fit_ref   1.126
_refine_ls_restrained_S_all      1.126
_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
Dy Dy 0.500000 0.20918(2) 0.750000 0.02967(8) Uani 1 2 d S T P A .
Cl Cl 0.500000 -0.04263(15) 0.750000 0.0666(5) Uani 1 2 d S T P . .
O1 O 0.59935(16) 0.2326(3) 0.6916(2) 0.0440(6) Uani 1 1 d . . . . .
C1 C 0.6526(2) 0.3167(4) 0.6796(3) 0.0426(9) Uani 1 1 d . . . . .
C2 C 0.6829(2) 0.4082(5) 0.7465(3) 0.0483(10) Uani 1 1 d . . . . .
C3 C 0.7391(3) 0.4963(6) 0.7329(4) 0.0626(13) Uani 1 1 d . . . . .
H3 H 0.758397 0.558685 0.777113 0.075 Uiso 1 1 calc R U . . .
C4 C 0.7664(3) 0.4918(6) 0.6550(4) 0.0719(16) Uani 1 1 d . . . . .
H4 H 0.804590 0.549910 0.647296 0.086 Uiso 1 1 calc R U . . .
C5 C 0.7377(3) 0.4031(6) 0.5895(4) 0.0694(16) Uani 1 1 d . . . . .
H5 H 0.756355 0.400634 0.536897 0.083 Uiso 1 1 calc R U . . .
C6 C 0.6810(3) 0.3163(5) 0.5997(3) 0.0552(11) Uani 1 1 d . . . . .
H6 H 0.661230 0.256878 0.553594 0.066 Uiso 1 1 calc R U . . .
C7 C 0.6573(3) 0.4061(5) 0.8348(3) 0.0535(11) Uani 1 1 d . . . . .
H7A H 0.675753 0.326226 0.866985 0.064 Uiso 1 1 calc R U . . .
H7B H 0.682009 0.477878 0.872465 0.064 Uiso 1 1 calc R U . . .
N2 N 0.5716(2) 0.4152(3) 0.8242(2) 0.0428(7) Uani 1 1 d . . . . .
C8 C 0.5562(3) 0.4205(5) 0.9163(3) 0.0566(11) Uani 1 1 d . . . . .
H8A H 0.501345 0.438123 0.910676 0.068 Uiso 1 1 calc R U . . .
H8B H 0.585844 0.491056 0.950615 0.068 Uiso 1 1 calc R U . . .
C9 C 0.5779(2) 0.2941(5) 0.9673(3) 0.0473(9) Uani 1 1 d . . . . .
C10 C 0.6068(3) 0.2950(6) 1.0613(3) 0.0623(13) Uani 1 1 d . . . . .
H10 H 0.616861 0.373216 1.092877 0.075 Uiso 1 1 calc R U . . .
C11 C 0.6201(3) 0.1803(7) 1.1065(3) 0.0706(16) Uani 1 1 d . . . . .
H11 H 0.638407 0.179233 1.169643 0.085 Uiso 1 1 calc R U . . .
C12 C 0.6065(3) 0.0656(6) 1.0588(3) 0.0662(15) Uani 1 1 d . . . . .
H12 H 0.614581 -0.013810 1.088925 0.079 Uiso 1 1 calc R U . . .
C13 C 0.5803(3) 0.0710(5) 0.9644(3) 0.0527(11) Uani 1 1 d . . . . .
H13 H 0.572811 -0.006323 0.931572 0.063 Uiso 1 1 calc R U . . .
N1 N 0.56522(19) 0.1845(4) 0.9188(2) 0.0432(8) Uani 1 1 d . . . . .
C14A C 0.5431(3) 0.5356(4) 0.7684(3) 0.0540(11) Uani 0.5 1 d . . P A 1
H14 H 0.566366 0.533886 0.715631 0.065 Uiso 0.5 1 calc R U P A 1
C15 C 0.5781(6) 0.6600(8) 0.8278(7) 0.055(2) Uani 0.5 1 d . . P A 1
H15A H 0.568734 0.736259 0.790118 0.083 Uiso 0.5 1 calc R U P A 1
H15B H 0.633182 0.648771 0.851264 0.083 Uiso 0.5 1 calc R U P A 1
H15C H 0.553536 0.669509 0.877599 0.083 Uiso 0.5 1 calc R U P A 1
C14B C 0.5431(3) 0.5356(4) 0.7684(3) 0.0540(11) Uani 0.5 1 d . . P A 2
H14A H 0.583729 0.560854 0.738574 0.081 Uiso 0.5 1 calc R U P A 2
H14B H 0.539517 0.604357 0.811172 0.081 Uiso 0.5 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Dy O1 2.161(3) . ?
Dy O1 2.161(3) 2_656 ?
Dy N1 2.545(3) . ?
Dy N1 2.545(3) 2_656 ?
Dy N2 2.583(3) . ?
Dy N2 2.583(3) 2_656 ?
Dy Cl 2.5910(16) . ?
O1 C1 1.324(5) . ?
C1 C2 1.390(6) . ?
C1 C6 1.412(6) . ?
C2 C3 1.397(6) . ?
C2 C7 1.507(6) . ?
C3 C4 1.375(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.352(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.379(7) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N2 1.489(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
N2 C8 1.480(5) . ?
N2 C14B 1.515(5) . ?
N2 C14A 1.515(5) . ?
C8 C9 1.514(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N1 1.335(6) . ?
C9 C10 1.388(6) . ?
C10 C11 1.355(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.373(9) . ?
C11 H11 0.9300 . ?
C12 C13 1.389(6) . ?
C12 H12 0.9300 . ?
C13 N1 1.350(6) . ?
C13 H13 0.9300 . ?
C14A C14A 1.493(10) 2_656 ?
C14A C15 1.599(10) . ?
C14A H14 0.9800 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C14B H14A 0.9700 . ?
C14B H14B 0.9700 . ?

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 Dy O1 167.19(15) . 2_656 ?
O1 Dy N1 101.63(11) . . ?
O1 Dy N1 79.67(11) 2_656 . ?
O1 Dy N1 79.67(11) . 2_656 ?
O1 Dy N1 101.63(11) 2_656 2_656 ?
N1 Dy N1 168.55(17) . 2_656 ?
O1 Dy N2 73.92(11) . . ?
O1 Dy N2 95.39(11) 2_656 . ?
N1 Dy N2 65.81(11) . . ?
N1 Dy N2 125.00(11) 2_656 . ?
O1 Dy N2 95.39(11) . 2_656 ?
O1 Dy N2 73.92(11) 2_656 2_656 ?
N1 Dy N2 125.00(11) . 2_656 ?
N1 Dy N2 65.81(11) 2_656 2_656 ?
N2 Dy N2 69.71(15) . 2_656 ?
O1 Dy Cl 96.41(8) . . ?
O1 Dy Cl 96.40(8) 2_656 . ?
N1 Dy Cl 84.27(8) . . ?
N1 Dy Cl 84.27(8) 2_656 . ?
N2 Dy Cl 145.14(8) . . ?
N2 Dy Cl 145.14(8) 2_656 . ?
C1 O1 Dy 143.5(3) . . ?
O1 C1 C2 120.4(4) . . ?
O1 C1 C6 121.7(4) . . ?
C2 C1 C6 117.9(4) . . ?
C1 C2 C3 119.8(4) . . ?
C1 C2 C7 119.2(4) . . ?
C3 C2 C7 121.0(4) . . ?
C4 C3 C2 120.8(5) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 120.1(5) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.7(5) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 120.7(5) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
N2 C7 C2 114.7(3) . . ?
N2 C7 H7A 108.6 . . ?
C2 C7 H7A 108.6 . . ?
N2 C7 H7B 108.6 . . ?
C2 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
C8 N2 C7 108.3(3) . . ?
C8 N2 C14B 112.3(3) . . ?
C7 N2 C14B 107.8(3) . . ?
C8 N2 C14A 112.3(3) . . ?
C7 N2 C14A 107.8(3) . . ?
C8 N2 Dy 104.8(3) . . ?
C7 N2 Dy 112.1(3) . . ?
C14B N2 Dy 111.5(2) . . ?
C14A N2 Dy 111.5(2) . . ?
N2 C8 C9 111.4(4) . . ?
N2 C8 H8A 109.4 . . ?
C9 C8 H8A 109.4 . . ?
N2 C8 H8B 109.4 . . ?
C9 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
N1 C9 C10 122.6(5) . . ?
N1 C9 C8 117.2(4) . . ?
C10 C9 C8 120.1(5) . . ?
C11 C10 C9 119.0(5) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C10 C11 C12 119.8(5) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C13 118.5(5) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
N1 C13 C12 122.3(5) . . ?
N1 C13 H13 118.9 . . ?
C12 C13 H13 118.9 . . ?
C9 N1 C13 117.7(4) . . ?
C9 N1 Dy 116.2(3) . . ?
C13 N1 Dy 125.7(3) . . ?
C14A C14A N2 112.4(3) 2_656 . ?
C14A C14A C15 115.6(5) 2_656 . ?
N2 C14A C15 108.1(5) . . ?
C14A C14A C14A 23.3(3) 2_656 2 ?
N2 C14A C14A 121.4(2) . 2 ?
C15 C14A C14A 124.2(4) . 2 ?
C14A C14A H14 106.8 2_656 . ?
N2 C14A H14 106.8 . . ?
C15 C14A H14 106.8 . . ?
C14A C14A H14 83.4 2 . ?
C14A C15 H15A 109.5 . . ?
C14A C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14A C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C14B C14B 121.4(2) . 2 ?
N2 C14B H14A 107.0 . . ?
C14B C14B H14A 107.0 2 . ?
N2 C14B H14B 107.0 . . ?
C14B C14B H14B 107.0 2 . ?
H14A C14B H14B 106.7 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Dy O1 C1 C2 35.2(7) . . . . ?
Dy O1 C1 C6 -145.3(4) . . . . ?
O1 C1 C2 C3 179.9(4) . . . . ?
C6 C1 C2 C3 0.4(6) . . . . ?
O1 C1 C2 C7 3.1(6) . . . . ?
C6 C1 C2 C7 -176.4(4) . . . . ?
C1 C2 C3 C4 -1.5(7) . . . . ?
C7 C2 C3 C4 175.3(5) . . . . ?
C2 C3 C4 C5 1.3(8) . . . . ?
C3 C4 C5 C6 0.0(8) . . . . ?
C4 C5 C6 C1 -1.1(8) . . . . ?
O1 C1 C6 C5 -178.7(4) . . . . ?
C2 C1 C6 C5 0.8(7) . . . . ?
C1 C2 C7 N2 -56.0(6) . . . . ?
C3 C2 C7 N2 127.2(5) . . . . ?
C2 C7 N2 C8 -176.4(4) . . . . ?
C2 C7 N2 C14B -54.6(5) . . . . ?
C2 C7 N2 C14A -54.6(5) . . . . ?
C2 C7 N2 Dy 68.5(4) . . . . ?
C7 N2 C8 C9 -66.6(5) . . . . ?
C14B N2 C8 C9 174.5(4) . . . . ?
C14A N2 C8 C9 174.5(4) . . . . ?
Dy N2 C8 C9 53.2(4) . . . . ?
N2 C8 C9 N1 -36.1(6) . . . . ?
N2 C8 C9 C10 146.4(4) . . . . ?
N1 C9 C10 C11 -2.5(7) . . . . ?
C8 C9 C10 C11 174.9(5) . . . . ?
C9 C10 C11 C12 1.3(8) . . . . ?
C10 C11 C12 C13 1.0(8) . . . . ?
C11 C12 C13 N1 -2.4(7) . . . . ?
C10 C9 N1 C13 1.1(6) . . . . ?
C8 C9 N1 C13 -176.3(4) . . . . ?
C10 C9 N1 Dy 174.3(3) . . . . ?
C8 C9 N1 Dy -3.1(5) . . . . ?
C12 C13 N1 C9 1.4(6) . . . . ?
C12 C13 N1 Dy -171.2(3) . . . . ?
C8 N2 C14A C14A -76.6(5) . . . 2_656 ?
C7 N2 C14A C14A 164.1(4) . . . 2_656 ?
Dy N2 C14A C14A 40.7(5) . . . 2_656 ?
C8 N2 C14A C15 52.1(6) . . . . ?
C7 N2 C14A C15 -67.1(6) . . . . ?
Dy N2 C14A C15 169.5(5) . . . . ?
C8 N2 C14A C14A -100.8(3) . . . 2 ?
C7 N2 C14A C14A 139.9(2) . . . 2 ?
Dy N2 C14A C14A 16.5(3) . . . 2 ?
C8 N2 C14B C14B -100.8(3) . . . 2 ?
C7 N2 C14B C14B 139.9(2) . . . 2 ?
Dy N2 C14B C14B 16.5(3) . . . 2 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C15^a H15A^a Cl 0.96 2.58 3.446(9) 149.8 1_565 yes

_refine_diff_density_max         1.107
_refine_diff_density_min         -1.396
_refine_diff_density_rms         0.097


_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_preparation       'Magnetic properties'
####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2129445'
loop_
_audit_author_name
_audit_author_address
'Francielli Sousa Santana'
;Universidade Federal do Parana
Brazil
;
_audit_update_record             
;
2021-12-17 deposited with the CCDC.	2022-04-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_structural     '[YC29H30ClN4O2]'
_chemical_formula_moiety         'C29 H30 Cl N4 O2 Y'
_chemical_formula_sum            'C29 H30 Cl N4 O2 Y'
_chemical_formula_weight         590.93

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Y Y -2.7962 3.5667 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   17.7054(7)
_cell_length_b                   10.2696(4)
_cell_length_c                   15.0884(6)
_cell_angle_alpha                90
_cell_angle_beta                 104.0230(10)
_cell_angle_gamma                90
_cell_volume                     2661.72(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    300(2)
_cell_measurement_reflns_used    9492
_cell_measurement_theta_min      3.19
_cell_measurement_theta_max      26.16
_exptl_crystal_description       rhomb
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_F_000             1216
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_min          0.106
_exptl_crystal_size_mid          0.108
_exptl_crystal_size_max          0.227
_exptl_absorpt_coefficient_mu    2.325
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6685
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   
;
SADABS-2012/1 - Bruker AXS area detector scaling and absorption correction 
;
_diffrn_ambient_temperature      300(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 Venture/Photon 100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_reflns_number            35862
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.189
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2615
_reflns_number_gt                2353
_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 APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2015 (Sheldrick 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    'ORTEP (Johnson, 1976 and Farrugia, 2012)'
_computing_publication_material  
'SHELXL-2014/7 (Sheldrick, 2015) and WINGX (Farrugia, 2012)'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0332P)²+3.7418P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2615
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0370
_refine_ls_R_factor_gt           0.0306
_refine_ls_wR_factor_ref         0.0727
_refine_ls_wR_factor_gt          0.0705
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
Y Y 0.500000 0.21069(3) 0.750000 0.02785(10) Uani 1 2 d S T P A .
Cl Cl 0.500000 -0.04090(9) 0.750000 0.0625(3) Uani 1 2 d S T P . .
O1 O 0.40133(10) 0.23273(16) 0.80995(12) 0.0429(4) Uani 1 1 d . . . . .
N1 N 0.43432(12) 0.1852(2) 0.58145(13) 0.0392(5) Uani 1 1 d . . . . .
N2 N 0.42805(13) 0.41725(18) 0.67661(13) 0.0389(5) Uani 1 1 d . . . . .
C1 C 0.34753(14) 0.3159(2) 0.82145(17) 0.0384(5) Uani 1 1 d . . . . .
C2 C 0.31654(15) 0.4077(3) 0.75392(18) 0.0428(6) Uani 1 1 d . . . . .
C3 C 0.26002(16) 0.4951(3) 0.7676(2) 0.0547(7) Uani 1 1 d . . . . .
H3 H 0.240370 0.557401 0.723230 0.066 Uiso 1 1 calc R U . . .
C4 C 0.23291(17) 0.4904(3) 0.8457(2) 0.0628(9) Uani 1 1 d . . . . .
H4 H 0.194373 0.547864 0.853318 0.075 Uiso 1 1 calc R U . . .
C5 C 0.26276(18) 0.4011(3) 0.9121(2) 0.0605(8) Uani 1 1 d . . . . .
H5 H 0.244557 0.398245 0.964973 0.073 Uiso 1 1 calc R U . . .
C6 C 0.31980(17) 0.3150(3) 0.9013(2) 0.0503(7) Uani 1 1 d . . . . .
H6 H 0.340162 0.255595 0.947450 0.060 Uiso 1 1 calc R U . . .
C7 C 0.34190(16) 0.4053(3) 0.66597(18) 0.0492(7) Uani 1 1 d . . . . .
H7A H 0.324388 0.324408 0.634489 0.059 Uiso 1 1 calc R U . . .
H7B H 0.316311 0.476054 0.627615 0.059 Uiso 1 1 calc R U . . .
C8 C 0.44311(18) 0.4216(3) 0.58452(18) 0.0495(7) Uani 1 1 d . . . . .
H8A H 0.497857 0.439503 0.590129 0.059 Uiso 1 1 calc R U . . .
H8B H 0.413338 0.492190 0.550073 0.059 Uiso 1 1 calc R U . . .
C9 C 0.42188(14) 0.2966(3) 0.53326(16) 0.0412(6) Uani 1 1 d . . . . .
C10 C 0.39318(17) 0.2973(3) 0.43902(18) 0.0552(7) Uani 1 1 d . . . . .
H10 H 0.382898 0.375552 0.407404 0.066 Uiso 1 1 calc R U . . .
C11 C 0.38020(19) 0.1808(4) 0.3932(2) 0.0663(9) Uani 1 1 d . . . . .
H11 H 0.361986 0.179417 0.329969 0.080 Uiso 1 1 calc R U . . .
C12 C 0.39431(17) 0.0670(3) 0.4413(2) 0.0592(8) Uani 1 1 d . . . . .
H12 H 0.386650 -0.012818 0.411325 0.071 Uiso 1 1 calc R U . . .
C13 C 0.42023(15) 0.0724(3) 0.53570(19) 0.0481(6) Uani 1 1 d . . . . .
H13 H 0.428130 -0.005188 0.568471 0.058 Uiso 1 1 calc R U . . .
C14A C 0.45594(17) 0.5369(2) 0.73108(19) 0.0481(6) Uani 0.5 1 d . . P A 1
H14 H 0.433002 0.534744 0.784011 0.058 Uiso 0.5 1 calc R U P A 1
C15 C 0.4211(4) 0.6598(5) 0.6736(4) 0.0522(14) Uani 0.5 1 d . . P A 1
H15A H 0.431937 0.736034 0.711354 0.078 Uiso 0.5 1 calc R U P A 1
H15B H 0.365865 0.649543 0.651685 0.078 Uiso 0.5 1 calc R U P A 1
H15C H 0.444370 0.668835 0.622679 0.078 Uiso 0.5 1 calc R U P A 1
C14B C 0.45594(17) 0.5369(2) 0.73108(19) 0.0481(6) Uani 0.5 1 d . . P A 2
H14A H 0.501729 0.580351 0.720883 0.072 Uiso 0.5 1 calc R U P A 2
H14B H 0.449942 0.540992 0.793239 0.072 Uiso 0.5 1 calc R U P A 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Y O1 2.1650(16) 2_656 ?
Y O1 2.1650(16) . ?
Y N1 2.541(2) 2_656 ?
Y N1 2.541(2) . ?
Y N2 2.582(2) 2_656 ?
Y N2 2.5818(19) . ?
Y Cl 2.5837(9) . ?
O1 C1 1.321(3) . ?
N1 C13 1.341(3) . ?
N1 C9 1.345(3) . ?
N2 C8 1.478(3) . ?
N2 C14B 1.494(3) . ?
N2 C14A 1.494(3) . ?
N2 C7 1.499(3) . ?
C1 C2 1.399(4) . ?
C1 C6 1.407(3) . ?
C2 C3 1.396(4) . ?
C2 C7 1.501(4) . ?
C3 C4 1.378(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.366(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.498(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.389(4) . ?
C10 C11 1.372(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.368(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.387(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14A C14A 1.526(6) 2_656 ?
C14A C15 1.570(6) . ?
C14A C14A 18.917(6) 2 ?
C14A H14 0.9800 . ?
C14A H14A 1(10) 2_656 ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C14B C14B 18.917(6) 2 ?
C14B H14A 0.9700 . ?
C14B H14B 0.9700 . ?
C14B H14A 1(10) 2_656 ?

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 Y O1 168.00(9) 2_656 . ?
O1 Y N1 102.06(7) 2_656 2_656 ?
O1 Y N1 79.19(7) . 2_656 ?
O1 Y N1 79.19(7) 2_656 . ?
O1 Y N1 102.07(7) . . ?
N1 Y N1 168.17(10) 2_656 . ?
O1 Y N2 74.28(6) 2_656 2_656 ?
O1 Y N2 95.69(7) . 2_656 ?
N1 Y N2 66.22(6) 2_656 2_656 ?
N1 Y N2 124.93(7) . 2_656 ?
O1 Y N2 95.69(7) 2_656 . ?
O1 Y N2 74.28(6) . . ?
N1 Y N2 124.93(7) 2_656 . ?
N1 Y N2 66.22(6) . . ?
N2 Y N2 69.50(9) 2_656 . ?
O1 Y Cl 96.00(5) 2_656 . ?
O1 Y Cl 96.00(5) . . ?
N1 Y Cl 84.08(5) 2_656 . ?
N1 Y Cl 84.08(5) . . ?
N2 Y Cl 145.25(5) 2_656 . ?
N2 Y Cl 145.25(5) . . ?
C1 O1 Y 143.38(15) . . ?
C13 N1 C9 118.1(2) . . ?
C13 N1 Y 125.97(18) . . ?
C9 N1 Y 115.38(16) . . ?
C8 N2 C14B 112.4(2) . . ?
C8 N2 C14A 112.4(2) . . ?
C8 N2 C7 108.2(2) . . ?
C14B N2 C7 108.6(2) . . ?
C14A N2 C7 108.6(2) . . ?
C8 N2 Y 104.20(15) . . ?
C14B N2 Y 112.12(15) . . ?
C14A N2 Y 112.12(15) . . ?
C7 N2 Y 111.23(15) . . ?
O1 C1 C2 120.5(2) . . ?
O1 C1 C6 121.4(2) . . ?
C2 C1 C6 118.1(2) . . ?
C3 C2 C1 119.7(2) . . ?
C3 C2 C7 121.3(2) . . ?
C1 C2 C7 118.9(2) . . ?
C4 C3 C2 121.0(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C4 C3 119.9(3) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.5(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 120.9(3) . . ?
C5 C6 H6 119.5 . . ?
C1 C6 H6 119.5 . . ?
N2 C7 C2 114.7(2) . . ?
N2 C7 H7A 108.6 . . ?
C2 C7 H7A 108.6 . . ?
N2 C7 H7B 108.6 . . ?
C2 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
N2 C8 C9 112.3(2) . . ?
N2 C8 H8A 109.1 . . ?
C9 C8 H8A 109.1 . . ?
N2 C8 H8B 109.1 . . ?
C9 C8 H8B 109.1 . . ?
H8A C8 H8B 107.9 . . ?
N1 C9 C10 121.9(3) . . ?
N1 C9 C8 117.5(2) . . ?
C10 C9 C8 120.5(2) . . ?
C11 C10 C9 119.1(3) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C12 C11 C10 119.4(3) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C13 118.9(3) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
N1 C13 C12 122.5(3) . . ?
N1 C13 H13 118.8 . . ?
C12 C13 H13 118.8 . . ?
N2 C14A C14A 112.19(18) . 2_656 ?
N2 C14A C15 108.9(3) . . ?
C14A C14A C15 115.8(3) 2_656 . ?
N2 C14A C14A 58.05(13) . 2 ?
C14A C14A C14A 153.2(2) 2_656 2 ?
C15 C14A C14A 55.1(2) . 2 ?
N2 C14A H14 106.4 . . ?
C14A C14A H14 106.4 2_656 . ?
C15 C14A H14 106.4 . . ?
C14A C14A H14 100.4 2 . ?
N2 C14A H14A 148(10) . 2_656 ?
C14A C14A H14A 39(10) 2_656 2_656 ?
C15 C14A H14A 99(10) . 2_656 ?
C14A C14A H14A 154(10) 2 2_656 ?
H14 C14A H14A 78.9 . 2_656 ?
C14A C15 H15A 109.5 . . ?
C14A C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14A C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C14B C14B 58.05(13) . 2 ?
N2 C14B H14A 118.0 . . ?
C14B C14B H14A 118.0 2 . ?
N2 C14B H14B 118.0 . . ?
C14B C14B H14B 118.0 2 . ?
H14A C14B H14B 115.1 . . ?
N2 C14B H14A 148(10) . 2_656 ?
C14B C14B H14A 154(10) 2 2_656 ?
H14A C14B H14A 53.7 . 2_656 ?
H14B C14B H14A 61.6 . 2_656 ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Y O1 C1 C2 33.7(4) . . . . ?
Y O1 C1 C6 -146.3(2) . . . . ?
O1 C1 C2 C3 -179.7(2) . . . . ?
C6 C1 C2 C3 0.3(4) . . . . ?
O1 C1 C2 C7 3.5(4) . . . . ?
C6 C1 C2 C7 -176.5(2) . . . . ?
C1 C2 C3 C4 -1.5(4) . . . . ?
C7 C2 C3 C4 175.2(3) . . . . ?
C2 C3 C4 C5 1.5(5) . . . . ?
C3 C4 C5 C6 -0.3(5) . . . . ?
C4 C5 C6 C1 -1.0(5) . . . . ?
O1 C1 C6 C5 -179.1(3) . . . . ?
C2 C1 C6 C5 1.0(4) . . . . ?
C8 N2 C7 C2 -176.5(2) . . . . ?
C14B N2 C7 C2 -54.2(3) . . . . ?
C14A N2 C7 C2 -54.2(3) . . . . ?
Y N2 C7 C2 69.6(2) . . . . ?
C3 C2 C7 N2 126.5(3) . . . . ?
C1 C2 C7 N2 -56.8(3) . . . . ?
C14B N2 C8 C9 174.7(2) . . . . ?
C14A N2 C8 C9 174.7(2) . . . . ?
C7 N2 C8 C9 -65.4(3) . . . . ?
Y N2 C8 C9 53.0(2) . . . . ?
C13 N1 C9 C10 1.8(4) . . . . ?
Y N1 C9 C10 173.9(2) . . . . ?
C13 N1 C9 C8 -175.9(2) . . . . ?
Y N1 C9 C8 -3.7(3) . . . . ?
N2 C8 C9 N1 -35.7(3) . . . . ?
N2 C8 C9 C10 146.6(2) . . . . ?
N1 C9 C10 C11 -2.8(4) . . . . ?
C8 C9 C10 C11 174.8(3) . . . . ?
C9 C10 C11 C12 1.3(5) . . . . ?
C10 C11 C12 C13 1.1(5) . . . . ?
C9 N1 C13 C12 0.7(4) . . . . ?
Y N1 C13 C12 -170.5(2) . . . . ?
C11 C12 C13 N1 -2.1(4) . . . . ?
C8 N2 C14A C14A -76.9(3) . . . 2_656 ?
C7 N2 C14A C14A 163.4(2) . . . 2_656 ?
Y N2 C14A C14A 40.1(3) . . . 2_656 ?
C8 N2 C14A C15 52.6(4) . . . . ?
C7 N2 C14A C15 -67.1(3) . . . . ?
Y N2 C14A C15 169.6(3) . . . . ?
C8 N2 C14A C14A 74.87(18) . . . 2 ?
C7 N2 C14A C14A -44.82(14) . . . 2 ?
Y N2 C14A C14A -168.10(16) . . . 2 ?
C8 N2 C14B C14B 74.87(18) . . . 2 ?
C7 N2 C14B C14B -44.82(14) . . . 2 ?
Y N2 C14B C14B -168.10(16) . . . 2 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C15^a H15A^a Cl 0.96 2.59 3.457(5) 150.5 1_565 yes

_refine_diff_density_max         0.519
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.052


_exptl_crystal_recrystallization_method 'Vapour deposition'
_exptl_crystal_preparation       'Magnetic properties'
