# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_f1
_database_code_depnum_ccdc_archive 'CCDC 2050199'
_audit_update_record             
;
2020-12-14 deposited with the CCDC.	2021-03-26 downloaded from the CCDC.
;
_audit_creation_date             2020-02-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C21 H16 Cl2 Eu N3 O3'
_chemical_formula_sum            'C21 H16 Cl2 Eu N3 O3'
_chemical_formula_weight         581.23
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1'
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Eu Eu -0.1578 3.6682 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.9054(3)
_cell_length_b                   11.1091(3)
_cell_length_c                   18.3023(7)
_cell_angle_alpha                90
_cell_angle_beta                 92.827(3)
_cell_angle_gamma                90
_cell_volume                     2011.54(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4853
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.3920
_cell_measurement_theta_min      4.1880
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.413
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.27625
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_diffrn    1.919
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             1136
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.886
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14162
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.886
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.171
_diffrn_reflns_theta_min         3.481
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0233
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.886
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     21.00  60.00   1.00    3.00    --   18.63 -99.00 150.00   39
  2  ω    -84.00  10.00   1.00    3.00    --  -18.94 -77.00-120.00   94
  3  ω    -28.00  -2.00   1.00    3.00    --  -18.94 -57.00   0.00   26
  4  ω    -45.00  48.00   1.00    3.00    --  -18.94  77.00   0.00   93
  5  ω    -86.00  12.00   1.00    3.00    --  -18.94 -19.00  60.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0696017000
_diffrn_orient_matrix_UB_12      -0.0004090000
_diffrn_orient_matrix_UB_13      -0.0110775000
_diffrn_orient_matrix_UB_21      -0.0005873000
_diffrn_orient_matrix_UB_22      0.0638588000
_diffrn_orient_matrix_UB_23      0.0001832000
_diffrn_orient_matrix_UB_31      0.0169851000
_diffrn_orient_matrix_UB_32      0.0003757000
_diffrn_orient_matrix_UB_33      -0.0372069000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3894
_reflns_number_total             4820
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.741
_refine_diff_density_min         -1.210
_refine_diff_density_rms         0.122
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4820
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0320
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0239P)²+0.5360P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0608
_refine_ls_wR_factor_ref         0.0680
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Riding coordinates:
 O3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C15(H15),
 C16(H16), C17(H17), C19(H19), C20(H20), C21(H21)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Eu1 Eu 0.77242(2) 0.65182(2) 0.41607(2) 0.02464(7) Uani 1 1 d . . . . .
Cl1 Cl 0.50569(10) 0.64434(9) 0.44170(6) 0.0420(3) Uani 1 1 d . . . . .
Cl2 Cl 1.01964(10) 0.58301(9) 0.37552(5) 0.0363(2) Uani 1 1 d . . . . .
O1 O 0.7798(3) 0.8487(2) 0.42937(14) 0.0359(7) Uani 1 1 d . . . . .
O2 O 0.8626(3) 0.6893(2) 0.52897(14) 0.0406(7) Uani 1 1 d . . . . .
O3 O 0.7622(2) 0.4651(2) 0.48883(13) 0.0343(6) Uani 1 1 d . . . . .
H3A H 0.8277 0.4643 0.5211 0.051 Uiso 1 1 d R . . . .
H3B H 0.6671 0.4455 0.5013 0.051 Uiso 1 1 d R . . . .
N1 N 0.9006(3) 0.7812(3) 0.57126(16) 0.0298(7) Uani 1 1 d . . . . .
N2 N 0.7096(3) 0.7374(3) 0.28613(16) 0.0294(7) Uani 1 1 d . . . . .
N3 N 0.7053(3) 0.4956(3) 0.31483(16) 0.0297(7) Uani 1 1 d . . . . .
C1 C 0.7133(4) 0.3778(3) 0.3260(2) 0.0365(9) Uani 1 1 d . . . . .
H1 H 0.7458 0.3507 0.3716 0.044 Uiso 1 1 calc R . . . .
C2 C 0.6755(4) 0.2924(4) 0.2730(2) 0.0417(10) Uani 1 1 d . . . . .
H2 H 0.6853 0.2107 0.2828 0.050 Uiso 1 1 calc R . . . .
C3 C 0.6245(4) 0.3303(4) 0.2071(2) 0.0443(11) Uani 1 1 d . . . . .
H3 H 0.5971 0.2743 0.1717 0.053 Uiso 1 1 calc R . . . .
C4 C 0.6127(4) 0.4533(4) 0.1921(2) 0.0357(9) Uani 1 1 d . . . . .
C5 C 0.5609(4) 0.4993(5) 0.1233(2) 0.0456(12) Uani 1 1 d . . . . .
H5 H 0.5257 0.4465 0.0879 0.055 Uiso 1 1 calc R . . . .
C6 C 0.5624(4) 0.6175(4) 0.1094(2) 0.0452(11) Uani 1 1 d . . . . .
H6 H 0.5283 0.6451 0.0642 0.054 Uiso 1 1 calc R . . . .
C7 C 0.6150(4) 0.7028(4) 0.1623(2) 0.0355(9) Uani 1 1 d . . . . .
C8 C 0.6236(4) 0.8251(4) 0.1484(2) 0.0460(11) Uani 1 1 d . . . . .
H8 H 0.5933 0.8556 0.1032 0.055 Uiso 1 1 calc R . . . .
C9 C 0.6765(4) 0.9009(4) 0.2011(2) 0.0438(11) Uani 1 1 d . . . . .
H9 H 0.6859 0.9827 0.1918 0.053 Uiso 1 1 calc R . . . .
C10 C 0.7158(4) 0.8530(3) 0.2688(2) 0.0390(10) Uani 1 1 d . . . . .
H10 H 0.7491 0.9059 0.3047 0.047 Uiso 1 1 calc R . . . .
C11 C 0.6598(4) 0.6609(3) 0.2323(2) 0.0309(9) Uani 1 1 d . . . . .
C12 C 0.6585(3) 0.5342(3) 0.2478(2) 0.0294(8) Uani 1 1 d . . . . .
C13 C 0.8715(3) 0.8991(3) 0.5502(2) 0.0278(8) Uani 1 1 d . . . . .
C14 C 0.8101(4) 0.9289(3) 0.4809(2) 0.0285(8) Uani 1 1 d . . . . .
C15 C 0.7816(4) 1.0496(3) 0.4664(2) 0.0401(10) Uani 1 1 d . . . . .
H15 H 0.7401 1.0712 0.4216 0.048 Uiso 1 1 calc R . . . .
C16 C 0.8144(5) 1.1391(3) 0.5182(3) 0.0476(12) Uani 1 1 d . . . . .
H16 H 0.7941 1.2190 0.5073 0.057 Uiso 1 1 calc R . . . .
C17 C 0.8754(4) 1.1112(4) 0.5842(3) 0.0455(12) Uani 1 1 d . . . . .
H17 H 0.8966 1.1721 0.6176 0.055 Uiso 1 1 calc R . . . .
C18 C 0.9068(4) 0.9914(3) 0.6024(2) 0.0341(9) Uani 1 1 d . . . . .
C19 C 0.9673(4) 0.9597(4) 0.6704(2) 0.0455(11) Uani 1 1 d . . . . .
H19 H 0.9879 1.0194 0.7048 0.055 Uiso 1 1 calc R . . . .
C20 C 0.9964(4) 0.8427(4) 0.6868(2) 0.0440(11) Uani 1 1 d . . . . .
H20 H 1.0391 0.8226 0.7315 0.053 Uiso 1 1 calc R . . . .
C21 C 0.9615(4) 0.7534(4) 0.6357(2) 0.0373(9) Uani 1 1 d . . . . .
H21 H 0.9810 0.6734 0.6468 0.045 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Eu1 Cl1 2.7073(10) . ?
Eu1 Cl2 2.7039(9) . ?
Eu1 O1 2.202(2) . ?
Eu1 O2 2.249(3) . ?
Eu1 O3 2.470(2) . ?
Eu1 N2 2.608(3) . ?
Eu1 N3 2.601(3) . ?
O1 C14 1.321(4) . ?
O2 N1 1.324(4) . ?
N1 C13 1.392(5) . ?
N1 C21 1.335(5) . ?
N2 C10 1.325(4) . ?
N2 C11 1.373(5) . ?
N3 C1 1.326(5) . ?
N3 C12 1.359(5) . ?
C1 C2 1.395(5) . ?
C2 C3 1.351(6) . ?
C3 C4 1.397(6) . ?
C4 C5 1.430(6) . ?
C4 C12 1.417(5) . ?
C5 C6 1.337(6) . ?
C6 C7 1.434(6) . ?
C7 C8 1.386(6) . ?
C7 C11 1.415(5) . ?
C8 C9 1.365(6) . ?
C9 C10 1.386(5) . ?
C11 C12 1.436(5) . ?
C13 C14 1.419(5) . ?
C13 C18 1.433(5) . ?
C14 C15 1.394(5) . ?
C15 C16 1.401(6) . ?
C16 C17 1.359(6) . ?
C17 C18 1.402(5) . ?
C18 C19 1.399(6) . ?
C19 C20 1.362(6) . ?
C20 C21 1.395(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl2 Eu1 Cl1 160.67(3) . . ?
O1 Eu1 Cl1 92.22(7) . . ?
O1 Eu1 Cl2 106.60(7) . . ?
O1 Eu1 O2 72.83(9) . . ?
O1 Eu1 O3 140.98(9) . . ?
O1 Eu1 N2 75.16(9) . . ?
O1 Eu1 N3 138.37(10) . . ?
O2 Eu1 Cl1 101.14(8) . . ?
O2 Eu1 Cl2 88.89(8) . . ?
O2 Eu1 O3 71.66(8) . . ?
O2 Eu1 N2 146.76(9) . . ?
O2 Eu1 N3 148.66(9) . . ?
O3 Eu1 Cl1 79.31(6) . . ?
O3 Eu1 Cl2 88.42(6) . . ?
O3 Eu1 N2 141.57(9) . . ?
O3 Eu1 N3 78.92(9) . . ?
N2 Eu1 Cl1 88.75(7) . . ?
N2 Eu1 Cl2 91.79(6) . . ?
N3 Eu1 Cl1 83.42(7) . . ?
N3 Eu1 Cl2 79.58(7) . . ?
N3 Eu1 N2 63.40(9) . . ?
C14 O1 Eu1 138.9(2) . . ?
N1 O2 Eu1 140.2(2) . . ?
O2 N1 C13 121.0(3) . . ?
O2 N1 C21 116.2(3) . . ?
C21 N1 C13 122.7(3) . . ?
C10 N2 Eu1 124.1(3) . . ?
C10 N2 C11 116.6(3) . . ?
C11 N2 Eu1 119.3(2) . . ?
C1 N3 Eu1 122.5(3) . . ?
C1 N3 C12 117.7(3) . . ?
C12 N3 Eu1 119.8(2) . . ?
N3 C1 C2 123.5(4) . . ?
C3 C2 C1 119.0(4) . . ?
C2 C3 C4 120.3(4) . . ?
C3 C4 C5 123.1(4) . . ?
C3 C4 C12 117.2(4) . . ?
C12 C4 C5 119.7(4) . . ?
C6 C5 C4 120.8(4) . . ?
C5 C6 C7 121.8(4) . . ?
C8 C7 C6 123.2(4) . . ?
C8 C7 C11 118.0(4) . . ?
C11 C7 C6 118.8(4) . . ?
C9 C8 C7 120.0(4) . . ?
C8 C9 C10 118.4(4) . . ?
N2 C10 C9 124.9(4) . . ?
N2 C11 C7 122.1(4) . . ?
N2 C11 C12 118.2(3) . . ?
C7 C11 C12 119.7(4) . . ?
N3 C12 C4 122.2(4) . . ?
N3 C12 C11 118.7(3) . . ?
C4 C12 C11 119.0(4) . . ?
N1 C13 C14 122.7(3) . . ?
N1 C13 C18 116.7(3) . . ?
C14 C13 C18 120.6(3) . . ?
O1 C14 C13 123.6(3) . . ?
O1 C14 C15 118.4(4) . . ?
C15 C14 C13 117.9(3) . . ?
C14 C15 C16 121.1(4) . . ?
C17 C16 C15 121.2(4) . . ?
C16 C17 C18 120.8(4) . . ?
C17 C18 C13 118.4(4) . . ?
C19 C18 C13 119.5(4) . . ?
C19 C18 C17 122.0(4) . . ?
C20 C19 C18 120.9(4) . . ?
C19 C20 C21 119.2(4) . . ?
N1 C21 C20 121.0(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.084
_oxdiff_exptl_absorpt_empirical_full_min 0.393
####################################################################### 
# 
# 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_61
_database_code_depnum_ccdc_archive 'CCDC 2050201'
_audit_update_record             
;
2020-12-14 deposited with the CCDC.	2021-03-26 downloaded from the CCDC.
;
_audit_creation_date             2019-09-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C21 H16 Cl2 Er N3 O3'
_chemical_formula_sum            'C21 H16 Cl2 Er N3 O3'
_chemical_formula_weight         596.53
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.8863(6)
_cell_length_b                   11.0534(14)
_cell_length_c                   18.1992(12)
_cell_angle_alpha                90
_cell_angle_beta                 93.259(6)
_cell_angle_gamma                90
_cell_volume                     1985.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5335
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.9360
_cell_measurement_theta_min      3.6670
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.525
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36617
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.996
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1156
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0443
_diffrn_reflns_av_unetI/netI     0.0544
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.887
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13513
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.887
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.082
_diffrn_reflns_theta_min         3.487
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0233
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.887
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     21.00  60.00   1.00    7.00    --   18.63 -99.00-180.00   39
  2  ω    -82.00   6.00   1.00    7.00    --  -18.94 -77.00 -90.00   88
  3  ω    -26.00  -1.00   1.00    7.00    --  -18.94 -57.00  30.00   25
  4  ω    -49.00  50.00   1.00    7.00    --  -18.94  77.00  30.00   99
  5  ω    -86.00  10.00   1.00    7.00    --  -18.94 -19.00  90.00   96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0712928000
_diffrn_orient_matrix_UB_12      0.0064631000
_diffrn_orient_matrix_UB_13      -0.0010132000
_diffrn_orient_matrix_UB_21      -0.0075341000
_diffrn_orient_matrix_UB_22      -0.0638098000
_diffrn_orient_matrix_UB_23      0.0023975000
_diffrn_orient_matrix_UB_31      0.0025581000
_diffrn_orient_matrix_UB_32      0.0041633000
_diffrn_orient_matrix_UB_33      0.0389546000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3806
_reflns_number_total             4723
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.626
_refine_diff_density_min         -1.207
_refine_diff_density_rms         0.167
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4723
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0495
_refine_ls_R_factor_gt           0.0357
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0238P)²+3.2267P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0711
_refine_ls_wR_factor_ref         0.0842
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Rotating group:
 O3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C10(H10), C11(H11), C12(H12),
 C14(H14), C15(H15), C17(H17), C18(H18), C19(H19)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Er1 Er 0.77064(2) 0.65071(2) 0.91624(2) 0.02551(8) Uani 1 1 d . . . . .
Cl1 Cl 1.01363(13) 0.58800(12) 0.87726(7) 0.0356(3) Uani 1 1 d . . . . .
Cl2 Cl 0.50967(14) 0.64453(13) 0.94137(8) 0.0407(3) Uani 1 1 d . . . . .
O1 O 0.7783(4) 0.8446(3) 0.9290(2) 0.0367(9) Uani 1 1 d . . . . .
O2 O 0.8591(4) 0.6831(3) 1.02839(19) 0.0395(10) Uani 1 1 d . . . . .
O3 O 0.7631(4) 0.4661(3) 0.98680(18) 0.0348(9) Uani 1 1 d . . . . .
H3A H 0.6832 0.4560 1.0046 0.052 Uiso 1 1 d GR . . . .
H3B H 0.8175 0.4712 1.0264 0.052 Uiso 1 1 d GR . . . .
N1 N 0.8984(4) 0.7750(4) 1.0712(2) 0.0307(10) Uani 1 1 d . . . . .
N2 N 0.7108(4) 0.7365(4) 0.7891(2) 0.0299(10) Uani 1 1 d . . . . .
N3 N 0.7065(4) 0.4945(4) 0.8180(2) 0.0275(9) Uani 1 1 d . . . . .
C1 C 0.9609(5) 0.7476(5) 1.1356(3) 0.0345(12) Uani 1 1 d . . . . .
H1 H 0.9808 0.6671 1.1464 0.041 Uiso 1 1 calc R . . . .
C2 C 0.9973(6) 0.8364(6) 1.1872(3) 0.0424(15) Uani 1 1 d . . . . .
H2 H 1.0414 0.8156 1.2319 0.051 Uiso 1 1 calc R . . . .
C3 C 0.9678(5) 0.9530(6) 1.1716(3) 0.0397(14) Uani 1 1 d . . . . .
H3 H 0.9887 1.0121 1.2068 0.048 Uiso 1 1 calc R . . . .
C4 C 0.9058(5) 0.9874(5) 1.1030(3) 0.0316(12) Uani 1 1 d . . . . .
C5 C 0.8758(6) 1.1091(5) 1.0850(3) 0.0429(15) Uani 1 1 d . . . . .
H5 H 0.8977 1.1702 1.1188 0.051 Uiso 1 1 calc R . . . .
C6 C 0.8154(7) 1.1365(5) 1.0189(4) 0.0458(16) Uani 1 1 d . . . . .
H6 H 0.7958 1.2168 1.0074 0.055 Uiso 1 1 calc R . . . .
C7 C 0.7818(5) 1.0461(5) 0.9675(3) 0.0380(13) Uani 1 1 d . . . . .
H7 H 0.7392 1.0682 0.9226 0.046 Uiso 1 1 calc R . . . .
C8 C 0.8095(5) 0.9250(4) 0.9805(3) 0.0262(11) Uani 1 1 d . . . . .
C9 C 0.8705(5) 0.8952(5) 1.0503(3) 0.0277(11) Uani 1 1 d . . . . .
C10 C 0.7195(6) 0.8529(5) 0.7710(3) 0.0356(13) Uani 1 1 d . . . . .
H10 H 0.7554 0.9055 0.8069 0.043 Uiso 1 1 calc R . . . .
C11 C 0.6797(6) 0.9017(6) 0.7039(3) 0.0433(14) Uani 1 1 d . . . . .
H11 H 0.6892 0.9841 0.6952 0.052 Uiso 1 1 calc R . . . .
C12 C 0.6257(6) 0.8263(6) 0.6498(3) 0.0437(15) Uani 1 1 d . . . . .
H12 H 0.5962 0.8571 0.6041 0.052 Uiso 1 1 calc R . . . .
C13 C 0.6158(5) 0.7021(5) 0.6646(3) 0.0338(12) Uani 1 1 d . . . . .
C14 C 0.5624(6) 0.6169(6) 0.6105(3) 0.0461(16) Uani 1 1 d . . . . .
H14 H 0.5278 0.6450 0.5651 0.055 Uiso 1 1 calc R . . . .
C15 C 0.5617(6) 0.4981(6) 0.6246(3) 0.0423(15) Uani 1 1 d . . . . .
H15 H 0.5272 0.4449 0.5886 0.051 Uiso 1 1 calc R . . . .
C16 C 0.6133(5) 0.4515(5) 0.6942(3) 0.0343(12) Uani 1 1 d . . . . .
C17 C 0.6254(6) 0.3279(5) 0.7094(3) 0.0384(14) Uani 1 1 d . . . . .
H17 H 0.5984 0.2717 0.6734 0.046 Uiso 1 1 calc R . . . .
C18 C 0.6757(6) 0.2891(5) 0.7757(3) 0.0394(13) Uani 1 1 d . . . . .
H18 H 0.6845 0.2069 0.7856 0.047 Uiso 1 1 calc R . . . .
C19 C 0.7145(5) 0.3757(5) 0.8294(3) 0.0353(13) Uani 1 1 d . . . . .
H19 H 0.7475 0.3485 0.8754 0.042 Uiso 1 1 calc R . . . .
C20 C 0.6593(5) 0.5324(5) 0.7506(3) 0.0280(11) Uani 1 1 d . . . . .
C21 C 0.6617(5) 0.6607(5) 0.7345(3) 0.0307(12) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Er1 Cl1 2.6359(14) . ?
Er1 Cl2 2.6466(14) . ?
Er1 O1 2.157(3) . ?
Er1 O2 2.204(3) . ?
Er1 O3 2.414(3) . ?
Er1 N2 2.539(4) . ?
Er1 N3 2.540(4) . ?
O1 C8 1.316(6) . ?
O2 N1 1.324(5) . ?
N1 C1 1.328(6) . ?
N1 C9 1.405(6) . ?
N2 C10 1.332(6) . ?
N2 C21 1.368(6) . ?
N3 C19 1.332(6) . ?
N3 C20 1.354(6) . ?
C1 C2 1.392(7) . ?
C2 C3 1.348(8) . ?
C3 C4 1.411(7) . ?
C4 C5 1.411(8) . ?
C4 C9 1.429(7) . ?
C5 C6 1.347(9) . ?
C6 C7 1.396(8) . ?
C7 C8 1.384(7) . ?
C8 C9 1.414(7) . ?
C10 C11 1.372(7) . ?
C11 C12 1.374(8) . ?
C12 C13 1.404(8) . ?
C13 C14 1.440(8) . ?
C13 C21 1.403(7) . ?
C14 C15 1.338(8) . ?
C15 C16 1.434(7) . ?
C16 C17 1.398(8) . ?
C16 C20 1.416(7) . ?
C17 C18 1.348(8) . ?
C18 C19 1.406(7) . ?
C20 C21 1.448(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Er1 Cl2 162.18(5) . . ?
O1 Er1 Cl1 105.28(11) . . ?
O1 Er1 Cl2 92.03(11) . . ?
O1 Er1 O2 74.27(13) . . ?
O1 Er1 O3 141.67(12) . . ?
O1 Er1 N2 74.45(13) . . ?
O1 Er1 N3 139.21(13) . . ?
O2 Er1 Cl1 88.42(11) . . ?
O2 Er1 Cl2 100.57(12) . . ?
O2 Er1 O3 70.57(12) . . ?
O2 Er1 N2 147.44(14) . . ?
O2 Er1 N3 146.38(13) . . ?
O3 Er1 Cl1 88.69(10) . . ?
O3 Er1 Cl2 80.00(10) . . ?
O3 Er1 N2 141.98(13) . . ?
O3 Er1 N3 77.65(12) . . ?
N2 Er1 Cl1 91.24(10) . . ?
N2 Er1 Cl2 89.33(10) . . ?
N2 Er1 N3 64.94(13) . . ?
N3 Er1 Cl1 80.01(10) . . ?
N3 Er1 Cl2 84.11(10) . . ?
C8 O1 Er1 138.9(3) . . ?
N1 O2 Er1 139.2(3) . . ?
O2 N1 C1 116.8(4) . . ?
O2 N1 C9 121.3(4) . . ?
C1 N1 C9 121.9(4) . . ?
C10 N2 Er1 124.9(4) . . ?
C10 N2 C21 115.9(5) . . ?
C21 N2 Er1 119.2(3) . . ?
C19 N3 Er1 123.4(3) . . ?
C19 N3 C20 117.4(4) . . ?
C20 N3 Er1 119.2(3) . . ?
N1 C1 C2 121.6(5) . . ?
C3 C2 C1 119.2(5) . . ?
C2 C3 C4 121.4(5) . . ?
C3 C4 C5 122.5(5) . . ?
C3 C4 C9 118.6(5) . . ?
C5 C4 C9 118.9(5) . . ?
C6 C5 C4 119.9(5) . . ?
C5 C6 C7 121.0(5) . . ?
C8 C7 C6 122.6(5) . . ?
O1 C8 C7 119.6(5) . . ?
O1 C8 C9 123.6(4) . . ?
C7 C8 C9 116.7(5) . . ?
N1 C9 C4 117.1(5) . . ?
N1 C9 C8 122.0(4) . . ?
C8 C9 C4 120.8(5) . . ?
N2 C10 C11 125.5(6) . . ?
C10 C11 C12 118.7(6) . . ?
C11 C12 C13 118.9(5) . . ?
C12 C13 C14 122.4(5) . . ?
C21 C13 C12 118.0(5) . . ?
C21 C13 C14 119.6(6) . . ?
C15 C14 C13 121.1(6) . . ?
C14 C15 C16 121.0(5) . . ?
C17 C16 C15 123.2(5) . . ?
C17 C16 C20 117.0(5) . . ?
C20 C16 C15 119.8(5) . . ?
C18 C17 C16 120.7(5) . . ?
C17 C18 C19 118.6(5) . . ?
N3 C19 C18 123.5(5) . . ?
N3 C20 C16 122.7(5) . . ?
N3 C20 C21 118.5(4) . . ?
C16 C20 C21 118.7(5) . . ?
N2 C21 C13 122.9(5) . . ?
N2 C21 C20 117.5(4) . . ?
C13 C21 C20 119.6(5) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.372
_oxdiff_exptl_absorpt_empirical_full_min 0.557
####################################################################### 
# 
# 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_222
_database_code_depnum_ccdc_archive 'CCDC 2050203'
_audit_update_record             
;
2020-12-14 deposited with the CCDC.	2021-03-26 downloaded from the CCDC.
;
_audit_creation_date             2019-06-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H16 Cl2 Ho N3 O3'
_chemical_formula_sum            'C21 H16 Cl2 Ho N3 O3'
_chemical_formula_weight         594.20
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.8801(6)
_cell_length_b                   11.0521(7)
_cell_length_c                   18.2125(11)
_cell_angle_alpha                90
_cell_angle_beta                 93.202(2)
_cell_angle_gamma                90
_cell_volume                     1985.6(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9883
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.523
_cell_measurement_theta_min      2.942
_shelx_estimated_absorpt_T_max   0.650
_shelx_estimated_absorpt_T_min   0.453
_exptl_absorpt_coefficient_mu    4.284
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.3489
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1204 before and 0.0476 after correction.
The Ratio of minimum to maximum transmission is 0.4679.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.988
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1152
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0279
_diffrn_reflns_av_unetI/netI     0.0198
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            30363
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.540
_diffrn_reflns_theta_min         2.901
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4122
_reflns_number_total             4568
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         1.373
_refine_diff_density_min         -0.889
_refine_diff_density_rms         0.087
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4568
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0265
_refine_ls_R_factor_gt           0.0221
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0200P)²+2.9690P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0501
_refine_ls_wR_factor_ref         0.0516
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 H3B-H21
 2.2 with sigma of 0.02
3.a Rotating group:
 O3(H3A,H3B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C21(H21), C17(H17), C1(H1), C9(H9), C19(H19), C2(H2), C20(H20),
 C7(H7), C18(H18), C8(H8), C10(H10), C12(H12), C11(H11)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Ho1 Ho 0.27044(2) 0.15118(2) 0.41625(2) 0.02306(5) Uani 1 1 d . . . . .
Cl1 Cl 0.51429(7) 0.08742(7) 0.37716(4) 0.03359(16) Uani 1 1 d . . . . .
Cl2 Cl 0.00839(8) 0.14427(8) 0.44139(5) 0.04044(19) Uani 1 1 d . . . . .
O3 O 0.2610(2) -0.03315(19) 0.48742(11) 0.0339(5) Uani 1 1 d . . . . .
H3A H 0.268379 -0.017081 0.534998 0.051 Uiso 1 1 d GR . . . .
H3B H 0.332372 -0.079570 0.481099 0.051 Uiso 1 1 d DGR . . . .
O2 O 0.2783(2) 0.34547(18) 0.42895(12) 0.0365(5) Uani 1 1 d . . . . .
O1 O 0.3599(3) 0.18392(19) 0.52889(12) 0.0399(6) Uani 1 1 d . . . . .
N3 N 0.2054(2) -0.0054(2) 0.31736(13) 0.0278(5) Uani 1 1 d . . . . .
N1 N 0.3988(2) 0.2768(2) 0.57114(13) 0.0284(5) Uani 1 1 d . . . . .
N2 N 0.2103(2) 0.2366(2) 0.28857(13) 0.0292(5) Uani 1 1 d . . . . .
C15 C 0.1590(3) 0.0334(3) 0.24959(15) 0.0273(6) Uani 1 1 d . . . . .
C3 C 0.4683(3) 0.4542(3) 0.67189(18) 0.0420(8) Uani 1 1 d . . . . .
H3 H 0.490262 0.513376 0.706832 0.050 Uiso 1 1 calc R . . . .
C5 C 0.3706(3) 0.3950(3) 0.55067(16) 0.0273(6) Uani 1 1 d . . . . .
C21 C 0.2138(3) -0.1233(3) 0.32909(18) 0.0350(7) Uani 1 1 d . . . . .
H21 H 0.246128 -0.150210 0.375179 0.042 Uiso 1 1 calc DR . . . .
C17 C 0.0616(3) -0.0015(4) 0.12458(17) 0.0432(9) Uani 1 1 d . . . . .
H17 H 0.026379 -0.054653 0.088860 0.052 Uiso 1 1 calc R . . . .
C14 C 0.1613(3) 0.1607(3) 0.23422(15) 0.0279(6) Uani 1 1 d . . . . .
C6 C 0.3087(3) 0.4254(2) 0.48057(16) 0.0265(6) Uani 1 1 d . . . . .
C16 C 0.1135(3) -0.0480(3) 0.19382(17) 0.0352(7) Uani 1 1 d . . . . .
C1 C 0.4606(3) 0.2480(3) 0.63571(16) 0.0346(7) Uani 1 1 d . . . . .
H1 H 0.480101 0.167333 0.646380 0.042 Uiso 1 1 calc R . . . .
C9 C 0.3768(4) 0.6084(3) 0.5852(2) 0.0436(9) Uani 1 1 d . . . . .
H9 H 0.399751 0.669511 0.618747 0.052 Uiso 1 1 calc R . . . .
C19 C 0.1249(3) -0.1719(3) 0.20859(19) 0.0414(8) Uani 1 1 d . . . . .
H19 H 0.097436 -0.228212 0.172839 0.050 Uiso 1 1 calc R . . . .
C2 C 0.4963(3) 0.3368(3) 0.68732(18) 0.0420(8) Uani 1 1 d . . . . .
H2 H 0.539258 0.315562 0.732223 0.050 Uiso 1 1 calc R . . . .
C20 C 0.1764(3) -0.2096(3) 0.27542(19) 0.0400(8) Uani 1 1 d . . . . .
H20 H 0.186719 -0.291674 0.285429 0.048 Uiso 1 1 calc R . . . .
C4 C 0.4061(3) 0.4876(3) 0.60326(18) 0.0338(7) Uani 1 1 d . . . . .
C7 C 0.2812(3) 0.5470(3) 0.46741(19) 0.0373(7) Uani 1 1 d . . . . .
H7 H 0.238767 0.569170 0.422559 0.045 Uiso 1 1 calc R . . . .
C18 C 0.0630(3) 0.1170(4) 0.11037(17) 0.0438(9) Uani 1 1 d . . . . .
H18 H 0.028869 0.144735 0.064812 0.053 Uiso 1 1 calc R . . . .
C13 C 0.1161(3) 0.2025(3) 0.16396(16) 0.0348(7) Uani 1 1 d . . . . .
C8 C 0.3147(4) 0.6367(3) 0.5187(2) 0.0433(8) Uani 1 1 d . . . . .
H8 H 0.294502 0.717034 0.507464 0.052 Uiso 1 1 calc R . . . .
C10 C 0.2184(4) 0.3535(3) 0.27202(18) 0.0366(7) Uani 1 1 d . . . . .
H10 H 0.252614 0.406161 0.308291 0.044 Uiso 1 1 calc R . . . .
C12 C 0.1254(4) 0.3260(4) 0.14936(18) 0.0435(8) Uani 1 1 d . . . . .
H12 H 0.095897 0.356704 0.103667 0.052 Uiso 1 1 calc R . . . .
C11 C 0.1784(4) 0.4016(3) 0.20324(18) 0.0430(8) Uani 1 1 d . . . . .
H11 H 0.187767 0.483933 0.194142 0.052 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Ho1 Cl1 2.6457(8) . ?
Ho1 Cl2 2.6554(8) . ?
Ho1 O3 2.419(2) . ?
Ho1 O2 2.161(2) . ?
Ho1 O1 2.218(2) . ?
Ho1 N3 2.553(2) . ?
Ho1 N2 2.549(2) . ?
O3 H3A 0.8836 . ?
O3 H3B 0.8850 . ?
O2 C6 1.313(3) . ?
O1 N1 1.327(3) . ?
N3 C15 1.362(4) . ?
N3 C21 1.323(4) . ?
N1 C5 1.382(4) . ?
N1 C1 1.333(4) . ?
N2 C14 1.365(4) . ?
N2 C10 1.330(4) . ?
C15 C14 1.435(4) . ?
C15 C16 1.411(4) . ?
C3 H3 0.9300 . ?
C3 C2 1.353(5) . ?
C3 C4 1.411(5) . ?
C5 C6 1.425(4) . ?
C5 C4 1.432(4) . ?
C21 H21 0.9300 . ?
C21 C20 1.400(4) . ?
C17 H17 0.9300 . ?
C17 C16 1.430(5) . ?
C17 C18 1.335(5) . ?
C14 C13 1.410(4) . ?
C6 C7 1.389(4) . ?
C16 C19 1.400(5) . ?
C1 H1 0.9300 . ?
C1 C2 1.391(4) . ?
C9 H9 0.9300 . ?
C9 C4 1.401(5) . ?
C9 C8 1.364(5) . ?
C19 H19 0.9300 . ?
C19 C20 1.358(5) . ?
C2 H2 0.9300 . ?
C20 H20 0.9300 . ?
C7 H7 0.9300 . ?
C7 C8 1.389(5) . ?
C18 H18 0.9300 . ?
C18 C13 1.436(5) . ?
C13 C12 1.395(5) . ?
C8 H8 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.398(5) . ?
C12 H12 0.9300 . ?
C12 C11 1.371(5) . ?
C11 H11 0.9300 . ?

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
Cl1 Ho1 Cl2 161.82(3) . . ?
O3 Ho1 Cl1 89.02(6) . . ?
O3 Ho1 Cl2 79.41(6) . . ?
O3 Ho1 N3 77.97(7) . . ?
O3 Ho1 N2 141.87(8) . . ?
O2 Ho1 Cl1 105.40(7) . . ?
O2 Ho1 Cl2 92.28(7) . . ?
O2 Ho1 O3 141.42(8) . . ?
O2 Ho1 O1 74.26(8) . . ?
O2 Ho1 N3 139.03(8) . . ?
O2 Ho1 N2 74.62(8) . . ?
O1 Ho1 Cl1 88.31(7) . . ?
O1 Ho1 Cl2 100.80(7) . . ?
O1 Ho1 O3 70.56(7) . . ?
O1 Ho1 N3 146.57(8) . . ?
O1 Ho1 N2 147.57(8) . . ?
N3 Ho1 Cl1 80.02(6) . . ?
N3 Ho1 Cl2 83.85(6) . . ?
N2 Ho1 Cl1 91.28(6) . . ?
N2 Ho1 Cl2 89.32(6) . . ?
N2 Ho1 N3 64.58(8) . . ?
Ho1 O3 H3A 110.6 . . ?
Ho1 O3 H3B 111.3 . . ?
H3A O3 H3B 102.8 . . ?
C6 O2 Ho1 138.68(19) . . ?
N1 O1 Ho1 138.59(18) . . ?
C15 N3 Ho1 119.02(19) . . ?
C21 N3 Ho1 122.9(2) . . ?
C21 N3 C15 118.1(3) . . ?
O1 N1 C5 121.8(2) . . ?
O1 N1 C1 115.4(3) . . ?
C1 N1 C5 122.7(3) . . ?
C14 N2 Ho1 119.28(19) . . ?
C10 N2 Ho1 123.5(2) . . ?
C10 N2 C14 117.1(3) . . ?
N3 C15 C14 118.5(2) . . ?
N3 C15 C16 122.0(3) . . ?
C16 C15 C14 119.5(3) . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
N1 C5 C6 122.3(2) . . ?
N1 C5 C4 117.2(3) . . ?
C6 C5 C4 120.5(3) . . ?
N3 C21 H21 118.4 . . ?
N3 C21 C20 123.1(3) . . ?
C20 C21 H21 118.4 . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C18 C17 C16 121.1(3) . . ?
N2 C14 C15 118.0(3) . . ?
N2 C14 C13 122.6(3) . . ?
C13 C14 C15 119.4(3) . . ?
O2 C6 C5 123.5(3) . . ?
O2 C6 C7 119.5(3) . . ?
C7 C6 C5 116.9(3) . . ?
C15 C16 C17 119.3(3) . . ?
C19 C16 C15 117.8(3) . . ?
C19 C16 C17 122.8(3) . . ?
N1 C1 H1 119.5 . . ?
N1 C1 C2 120.9(3) . . ?
C2 C1 H1 119.5 . . ?
C4 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C4 120.2(3) . . ?
C16 C19 H19 120.2 . . ?
C20 C19 C16 119.6(3) . . ?
C20 C19 H19 120.2 . . ?
C3 C2 C1 119.7(3) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C21 C20 H20 120.4 . . ?
C19 C20 C21 119.2(3) . . ?
C19 C20 H20 120.4 . . ?
C3 C4 C5 118.9(3) . . ?
C9 C4 C3 122.1(3) . . ?
C9 C4 C5 119.0(3) . . ?
C6 C7 H7 118.7 . . ?
C6 C7 C8 122.5(3) . . ?
C8 C7 H7 118.7 . . ?
C17 C18 H18 119.3 . . ?
C17 C18 C13 121.4(3) . . ?
C13 C18 H18 119.3 . . ?
C14 C13 C18 119.1(3) . . ?
C12 C13 C14 118.2(3) . . ?
C12 C13 C18 122.7(3) . . ?
C9 C8 C7 120.8(3) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
N2 C10 H10 118.1 . . ?
N2 C10 C11 123.8(3) . . ?
C11 C10 H10 118.1 . . ?
C13 C12 H12 120.4 . . ?
C11 C12 C13 119.1(3) . . ?
C11 C12 H12 120.4 . . ?
C10 C11 H11 120.4 . . ?
C12 C11 C10 119.2(3) . . ?
C12 C11 H11 120.4 . . ?

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
Ho1 O2 C6 C5 9.8(5) . . . . ?
Ho1 O2 C6 C7 -170.9(2) . . . . ?
Ho1 O1 N1 C5 9.1(4) . . . . ?
Ho1 O1 N1 C1 -174.0(2) . . . . ?
Ho1 N3 C15 C14 6.2(3) . . . . ?
Ho1 N3 C15 C16 -176.0(2) . . . . ?
Ho1 N3 C21 C20 179.0(2) . . . . ?
Ho1 N2 C14 C15 -6.3(3) . . . . ?
Ho1 N2 C14 C13 175.0(2) . . . . ?
Ho1 N2 C10 C11 -176.3(2) . . . . ?
O2 C6 C7 C8 -177.8(3) . . . . ?
O1 N1 C5 C6 -5.5(4) . . . . ?
O1 N1 C5 C4 174.4(3) . . . . ?
O1 N1 C1 C2 -174.8(3) . . . . ?
N3 C15 C14 N2 0.1(4) . . . . ?
N3 C15 C14 C13 178.8(3) . . . . ?
N3 C15 C16 C17 177.9(3) . . . . ?
N3 C15 C16 C19 -3.8(4) . . . . ?
N3 C21 C20 C19 -2.1(5) . . . . ?
N1 C5 C6 O2 -2.8(4) . . . . ?
N1 C5 C6 C7 177.8(3) . . . . ?
N1 C5 C4 C3 0.6(4) . . . . ?
N1 C5 C4 C9 -178.8(3) . . . . ?
N1 C1 C2 C3 -0.1(5) . . . . ?
N2 C14 C13 C18 -178.6(3) . . . . ?
N2 C14 C13 C12 1.7(4) . . . . ?
N2 C10 C11 C12 1.2(5) . . . . ?
C15 N3 C21 C20 -0.5(5) . . . . ?
C15 C14 C13 C18 2.7(4) . . . . ?
C15 C14 C13 C12 -177.0(3) . . . . ?
C15 C16 C19 C20 1.1(5) . . . . ?
C5 N1 C1 C2 2.1(5) . . . . ?
C5 C6 C7 C8 1.6(4) . . . . ?
C21 N3 C15 C14 -174.3(3) . . . . ?
C21 N3 C15 C16 3.5(4) . . . . ?
C17 C16 C19 C20 179.3(3) . . . . ?
C17 C18 C13 C14 -3.2(5) . . . . ?
C17 C18 C13 C12 176.6(3) . . . . ?
C14 N2 C10 C11 0.8(5) . . . . ?
C14 C15 C16 C17 -4.3(4) . . . . ?
C14 C15 C16 C19 174.0(3) . . . . ?
C14 C13 C12 C11 0.4(5) . . . . ?
C6 C5 C4 C3 -179.5(3) . . . . ?
C6 C5 C4 C9 1.1(4) . . . . ?
C6 C7 C8 C9 -0.1(5) . . . . ?
C16 C15 C14 N2 -177.8(2) . . . . ?
C16 C15 C14 C13 1.0(4) . . . . ?
C16 C17 C18 C13 -0.2(5) . . . . ?
C16 C19 C20 C21 1.7(5) . . . . ?
C1 N1 C5 C6 177.8(3) . . . . ?
C1 N1 C5 C4 -2.3(4) . . . . ?
C2 C3 C4 C5 1.2(5) . . . . ?
C2 C3 C4 C9 -179.4(3) . . . . ?
C4 C3 C2 C1 -1.5(5) . . . . ?
C4 C5 C6 O2 177.3(3) . . . . ?
C4 C5 C6 C7 -2.1(4) . . . . ?
C4 C9 C8 C7 -0.9(5) . . . . ?
C18 C17 C16 C15 4.0(5) . . . . ?
C18 C17 C16 C19 -174.2(3) . . . . ?
C18 C13 C12 C11 -179.4(3) . . . . ?
C13 C12 C11 C10 -1.8(5) . . . . ?
C8 C9 C4 C3 -179.0(3) . . . . ?
C8 C9 C4 C5 0.4(5) . . . . ?
C10 N2 C14 C15 176.5(3) . . . . ?
C10 N2 C14 C13 -2.2(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_f3
_database_code_depnum_ccdc_archive 'CCDC 2050200'
_audit_update_record             
;
2020-12-14 deposited with the CCDC.	2021-03-26 downloaded from the CCDC.
;
_audit_creation_date             2020-08-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H16 Cl2 N3 O3 Sm'
_chemical_formula_sum            'C21 H16 Cl2 N3 O3 Sm'
_chemical_formula_weight         579.62
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1'
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'
Cl Cl 0.1484 0.1585 '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'
Sm Sm -0.1638 3.4418 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.9116(3)
_cell_length_b                   11.0963(3)
_cell_length_c                   18.2882(5)
_cell_angle_alpha                90
_cell_angle_beta                 92.574(2)
_cell_angle_gamma                90
_cell_volume                     2009.35(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3979
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.5350
_cell_measurement_theta_min      3.5830
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.218
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52430
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_density_diffrn    1.916
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1132
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0436
_diffrn_reflns_av_unetI/netI     0.0575
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            14048
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.288
_diffrn_reflns_theta_min         3.488
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0233
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     21.00  60.00   1.00   10.00    --   18.63 -99.00  90.00   39
  2  ω    -89.00  10.00   1.00   10.00    --  -18.94 -77.00-180.00   99
  3  ω    -25.00   0.00   1.00   10.00    --  -18.94 -57.00 -60.00   25
  4  ω    -45.00  43.00   1.00   10.00    --  -18.94  77.00 -60.00   88
  5  ω    -83.00  11.00   1.00   10.00    --  -18.94 -19.00   0.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0573126000
_diffrn_orient_matrix_UB_12      0.0376447000
_diffrn_orient_matrix_UB_13      -0.0058868000
_diffrn_orient_matrix_UB_21      -0.0425506000
_diffrn_orient_matrix_UB_22      -0.0513919000
_diffrn_orient_matrix_UB_23      -0.0005037000
_diffrn_orient_matrix_UB_31      -0.0060784000
_diffrn_orient_matrix_UB_32      0.0050769000
_diffrn_orient_matrix_UB_33      0.0383787000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3763
_reflns_number_total             4851
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.816
_refine_diff_density_min         -0.709
_refine_diff_density_rms         0.134
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4851
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0241P)²+0.7066P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0689
_refine_ls_wR_factor_ref         0.0781
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Rotating group:
 O3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C21(H21), C10(H10), C9(H9), C2(H2), C4(H4), C20(H20), C19(H19), C3(H3),
 C16(H16), C8(H8), C12(H12), C7(H7), C11(H11), C15(H15)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Sm01 Sm 0.72658(2) 0.65167(2) 0.58454(2) 0.02420(8) Uani 1 1 d . . . . .
Cl1 Cl 0.47869(11) 0.58088(11) 0.62563(6) 0.0354(3) Uani 1 1 d . . . . .
Cl2 Cl 0.99441(12) 0.64394(12) 0.55837(7) 0.0422(3) Uani 1 1 d . . . . .
O1 O 0.7199(3) 0.8488(3) 0.57219(17) 0.0367(8) Uani 1 1 d . . . . .
O3 O 0.7365(3) 0.4656(3) 0.50888(16) 0.0348(7) Uani 1 1 d . . . . .
H3A H 0.7212 0.4025 0.5352 0.052 Uiso 1 1 d GR . . . .
H3B H 0.8184 0.4549 0.4957 0.052 Uiso 1 1 d GR . . . .
O2 O 0.6357(3) 0.6920(3) 0.47138(17) 0.0410(8) Uani 1 1 d . . . . .
N3 N 0.7936(3) 0.4943(3) 0.68575(19) 0.0292(9) Uani 1 1 d . . . . .
N2 N 0.7905(3) 0.7357(3) 0.71513(19) 0.0299(9) Uani 1 1 d . . . . .
C1 C 0.5996(4) 0.7831(3) 0.4297(2) 0.0145(8) Uani 1 1 d . . . . .
C21 C 0.7851(4) 0.3769(4) 0.6742(3) 0.0353(11) Uani 1 1 d . . . . .
H21 H 0.7518 0.3503 0.6287 0.042 Uiso 1 1 calc R . . . .
C18 C 0.8421(4) 0.5326(4) 0.7534(2) 0.0274(10) Uani 1 1 d . . . . .
N1 N 0.6916(4) 0.9302(4) 0.5210(2) 0.0458(11) Uani 1 1 d . . . . .
C14 C 0.8398(4) 0.6600(4) 0.7689(2) 0.0291(10) Uani 1 1 d . . . . .
C6 C 0.6273(4) 0.8998(4) 0.4502(2) 0.0260(10) Uani 1 1 d . . . . .
C10 C 0.7839(5) 0.8515(4) 0.7323(3) 0.0368(12) Uani 1 1 d . . . . .
H10 H 0.7498 0.9042 0.6965 0.044 Uiso 1 1 calc R . . . .
C9 C 0.7204(4) 1.0518(4) 0.5349(3) 0.0368(12) Uani 1 1 d . . . . .
H9 H 0.7620 1.0740 0.5794 0.044 Uiso 1 1 calc R . . . .
C2 C 0.5393(4) 0.7580(4) 0.3660(3) 0.0353(11) Uani 1 1 d . . . . .
H2 H 0.5193 0.6780 0.3547 0.042 Uiso 1 1 calc R . . . .
C4 C 0.5339(4) 0.9625(5) 0.3312(3) 0.0427(13) Uani 1 1 d . . . . .
H4 H 0.5131 1.0221 0.2967 0.051 Uiso 1 1 calc R . . . .
C20 C 0.8236(5) 0.2906(5) 0.7269(3) 0.0408(12) Uani 1 1 d . . . . .
H20 H 0.8140 0.2089 0.7169 0.049 Uiso 1 1 calc R . . . .
C19 C 0.8750(5) 0.3284(5) 0.7929(3) 0.0418(13) Uani 1 1 d . . . . .
H19 H 0.9019 0.2722 0.8284 0.050 Uiso 1 1 calc R . . . .
C5 C 0.5953(4) 0.9947(4) 0.3993(3) 0.0323(11) Uani 1 1 d . . . . .
C3 C 0.5047(5) 0.8465(5) 0.3152(3) 0.0435(13) Uani 1 1 d . . . . .
H3 H 0.4618 0.8261 0.2706 0.052 Uiso 1 1 calc R . . . .
C13 C 0.8853(4) 0.7013(5) 0.8379(3) 0.0353(11) Uani 1 1 d . . . . .
C17 C 0.8878(4) 0.4522(5) 0.8081(2) 0.0343(11) Uani 1 1 d . . . . .
C16 C 0.9389(5) 0.4970(5) 0.8762(3) 0.0446(14) Uani 1 1 d . . . . .
H16 H 0.9734 0.4432 0.9113 0.053 Uiso 1 1 calc R . . . .
C8 C 0.6875(5) 1.1404(4) 0.4827(3) 0.0436(14) Uani 1 1 d . . . . .
H8 H 0.7088 1.2203 0.4933 0.052 Uiso 1 1 calc R . . . .
C12 C 0.8773(5) 0.8237(5) 0.8527(3) 0.0447(14) Uani 1 1 d . . . . .
H12 H 0.9076 0.8536 0.8981 0.054 Uiso 1 1 calc R . . . .
C7 C 0.6258(5) 1.1136(4) 0.4174(3) 0.0413(13) Uani 1 1 d . . . . .
H7 H 0.6036 1.1749 0.3844 0.050 Uiso 1 1 calc R . . . .
C11 C 0.8244(5) 0.9000(5) 0.8002(3) 0.0448(13) Uani 1 1 d . . . . .
H11 H 0.8157 0.9820 0.8095 0.054 Uiso 1 1 calc R . . . .
C15 C 0.9386(5) 0.6151(6) 0.8914(3) 0.0457(14) Uani 1 1 d . . . . .
H15 H 0.9729 0.6421 0.9366 0.055 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Sm01 Cl1 2.7174(11) . ?
Sm01 Cl2 2.7199(12) . ?
Sm01 O1 2.200(3) . ?
Sm01 O3 2.490(3) . ?
Sm01 O2 2.264(3) . ?
Sm01 N3 2.609(4) . ?
Sm01 N2 2.615(4) . ?
O1 N1 1.322(5) . ?
O3 H3A 0.8665 . ?
O3 H3B 0.8657 . ?
O2 C1 1.307(4) . ?
N3 C21 1.321(5) . ?
N3 C18 1.375(5) . ?
N2 C14 1.366(5) . ?
N2 C10 1.324(5) . ?
C1 C6 1.372(6) . ?
C1 C2 1.314(6) . ?
C21 H21 0.9300 . ?
C21 C20 1.400(6) . ?
C18 C14 1.443(6) . ?
C18 C17 1.399(6) . ?
N1 C6 1.457(6) . ?
N1 C9 1.400(6) . ?
C14 C13 1.398(6) . ?
C6 C5 1.431(6) . ?
C10 H10 0.9300 . ?
C10 C11 1.397(6) . ?
C9 H9 0.9300 . ?
C9 C8 1.399(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.407(7) . ?
C4 C3 1.349(7) . ?
C20 H20 0.9300 . ?
C20 C19 1.356(7) . ?
C19 H19 0.9300 . ?
C19 C17 1.405(7) . ?
C5 C7 1.390(6) . ?
C3 H3 0.9300 . ?
C13 C12 1.388(7) . ?
C13 C15 1.452(7) . ?
C17 C16 1.415(6) . ?
C16 H16 0.9300 . ?
C16 C15 1.339(7) . ?
C8 H8 0.9300 . ?
C8 C7 1.350(7) . ?
C12 H12 0.9300 . ?
C12 C11 1.367(7) . ?
C7 H7 0.9300 . ?
C11 H11 0.9300 . ?
C15 H15 0.9300 . ?

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
Cl1 Sm01 Cl2 160.27(4) . . ?
O1 Sm01 Cl1 107.01(8) . . ?
O1 Sm01 Cl2 92.20(9) . . ?
O1 Sm01 O3 140.29(11) . . ?
O1 Sm01 O2 72.60(11) . . ?
O1 Sm01 N3 138.08(11) . . ?
O1 Sm01 N2 75.17(11) . . ?
O3 Sm01 Cl1 88.43(7) . . ?
O3 Sm01 Cl2 79.22(7) . . ?
O3 Sm01 N3 79.86(11) . . ?
O3 Sm01 N2 142.12(11) . . ?
O2 Sm01 Cl1 88.99(9) . . ?
O2 Sm01 Cl2 101.34(9) . . ?
O2 Sm01 O3 71.32(10) . . ?
O2 Sm01 N3 149.18(12) . . ?
O2 Sm01 N2 146.55(12) . . ?
N3 Sm01 Cl1 79.33(8) . . ?
N3 Sm01 Cl2 83.36(8) . . ?
N3 Sm01 N2 63.09(11) . . ?
N2 Sm01 Cl1 92.04(8) . . ?
N2 Sm01 Cl2 88.49(8) . . ?
N1 O1 Sm01 139.1(3) . . ?
Sm01 O3 H3A 110.4 . . ?
Sm01 O3 H3B 109.2 . . ?
H3A O3 H3B 103.5 . . ?
C1 O2 Sm01 140.6(3) . . ?
C21 N3 Sm01 122.3(3) . . ?
C21 N3 C18 117.8(4) . . ?
C18 N3 Sm01 120.0(3) . . ?
C14 N2 Sm01 120.1(3) . . ?
C10 N2 Sm01 123.3(3) . . ?
C10 N2 C14 116.5(4) . . ?
O2 C1 C6 121.7(4) . . ?
O2 C1 C2 117.0(4) . . ?
C2 C1 C6 121.3(4) . . ?
N3 C21 H21 118.3 . . ?
N3 C21 C20 123.4(5) . . ?
C20 C21 H21 118.3 . . ?
N3 C18 C14 118.1(4) . . ?
N3 C18 C17 122.3(4) . . ?
C17 C18 C14 119.5(4) . . ?
O1 N1 C6 122.9(4) . . ?
O1 N1 C9 119.7(4) . . ?
C9 N1 C6 117.5(4) . . ?
N2 C14 C18 118.0(4) . . ?
N2 C14 C13 122.6(4) . . ?
C13 C14 C18 119.4(4) . . ?
C1 C6 N1 122.3(4) . . ?
C1 C6 C5 118.7(4) . . ?
C5 C6 N1 118.9(4) . . ?
N2 C10 H10 117.7 . . ?
N2 C10 C11 124.7(5) . . ?
C11 C10 H10 117.7 . . ?
N1 C9 H9 119.5 . . ?
C8 C9 N1 121.0(5) . . ?
C8 C9 H9 119.5 . . ?
C1 C2 H2 118.9 . . ?
C1 C2 C3 122.2(5) . . ?
C3 C2 H2 118.9 . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C3 C4 C5 120.9(5) . . ?
C21 C20 H20 120.6 . . ?
C19 C20 C21 118.8(5) . . ?
C19 C20 H20 120.6 . . ?
C20 C19 H19 119.9 . . ?
C20 C19 C17 120.3(5) . . ?
C17 C19 H19 119.9 . . ?
C4 C5 C6 117.6(4) . . ?
C7 C5 C6 120.2(5) . . ?
C7 C5 C4 122.2(5) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 C2 119.2(5) . . ?
C4 C3 H3 120.4 . . ?
C14 C13 C15 119.1(5) . . ?
C12 C13 C14 118.6(5) . . ?
C12 C13 C15 122.3(5) . . ?
C18 C17 C19 117.3(4) . . ?
C18 C17 C16 119.8(5) . . ?
C19 C17 C16 122.8(5) . . ?
C17 C16 H16 119.3 . . ?
C15 C16 C17 121.5(5) . . ?
C15 C16 H16 119.3 . . ?
C9 C8 H8 119.0 . . ?
C7 C8 C9 122.1(5) . . ?
C7 C8 H8 119.0 . . ?
C13 C12 H12 120.3 . . ?
C11 C12 C13 119.4(5) . . ?
C11 C12 H12 120.3 . . ?
C5 C7 H7 119.8 . . ?
C8 C7 C5 120.3(5) . . ?
C8 C7 H7 119.8 . . ?
C10 C11 H11 120.9 . . ?
C12 C11 C10 118.2(5) . . ?
C12 C11 H11 120.9 . . ?
C13 C15 H15 119.7 . . ?
C16 C15 C13 120.6(5) . . ?
C16 C15 H15 119.7 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.486
_oxdiff_exptl_absorpt_empirical_full_min 0.504
####################################################################### 
# 
# 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_222_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2050205'
_audit_update_record             
;
2020-12-14 deposited with the CCDC.	2021-03-26 downloaded from the CCDC.
;
_audit_creation_date             2019-06-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H16 Cl2 Gd N3 O3'
_chemical_formula_sum            'C21 H16 Cl2 Gd N3 O3'
_chemical_formula_weight         586.52
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.8846(6)
_cell_length_b                   11.0552(6)
_cell_length_c                   18.2127(10)
_cell_angle_alpha                90
_cell_angle_beta                 93.014(2)
_cell_angle_gamma                90
_cell_volume                     1987.5(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9932
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.529
_cell_measurement_theta_min      3.026
_shelx_estimated_absorpt_T_max   0.630
_shelx_estimated_absorpt_T_min   0.516
_exptl_absorpt_coefficient_mu    3.636
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4435
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1095 before and 0.0453 after correction.
The Ratio of minimum to maximum transmission is 0.5948.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.960
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1140
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0260
_diffrn_reflns_av_unetI/netI     0.0149
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            40606
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.537
_diffrn_reflns_theta_min         2.900
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4199
_reflns_number_total             4574
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.38A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.38A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.445
_refine_diff_density_min         -0.623
_refine_diff_density_rms         0.143
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4574
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0215
_refine_ls_R_factor_gt           0.0176
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0470P)²+0.5070P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0558
_refine_ls_wR_factor_ref         0.0649
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Rotating group:
 O3(H3A,H3B)
2.b Aromatic/amide H refined with riding coordinates:
 C9(H9), C17(H17), C2(H2), C21(H21), C3(H3), C11(H11), C1(H1), C19(H19),
 C8(H8), C7(H7), C20(H20), C10(H10), C18(H18), C12(H12)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Gd1 Gd 0.27117(2) 0.84861(2) 0.41598(2) 0.02186(6) Uani 1 1 d . . . . .
Cl2 Cl 0.51610(6) 0.91431(6) 0.37648(4) 0.03489(14) Uani 1 1 d . . . . .
Cl1 Cl 0.00768(7) 0.85554(6) 0.44156(4) 0.04123(17) Uani 1 1 d . . . . .
O2 O 0.2788(2) 0.65348(15) 0.42847(13) 0.0374(5) Uani 1 1 d . . . . .
O1 O 0.3607(2) 0.81423(18) 0.52894(11) 0.0405(5) Uani 1 1 d . . . . .
O3 O 0.26233(19) 1.03390(16) 0.48758(10) 0.0354(4) Uani 1 1 d . . . . .
H3A H 0.317996 1.029922 0.525730 0.053 Uiso 1 1 d GR . . . .
H3B H 0.183927 1.040374 0.506068 0.053 Uiso 1 1 d GR . . . .
N1 N 0.3990(2) 0.72124(19) 0.57077(11) 0.0296(4) Uani 1 1 d . . . . .
N3 N 0.2057(2) 1.00513(19) 0.31666(11) 0.0292(4) Uani 1 1 d . . . . .
N2 N 0.2102(2) 0.7634(2) 0.28753(11) 0.0303(4) Uani 1 1 d . . . . .
C9 C 0.3762(3) 0.3900(3) 0.58460(18) 0.0436(7) Uani 1 1 d . . . . .
H9 H 0.399195 0.328901 0.618102 0.052 Uiso 1 1 calc R . . . .
C6 C 0.3089(2) 0.5731(2) 0.48043(14) 0.0282(5) Uani 1 1 d . . . . .
C17 C 0.0614(3) 1.0019(3) 0.12431(15) 0.0438(7) Uani 1 1 d . . . . .
H17 H 0.026430 1.055166 0.088623 0.053 Uiso 1 1 calc R . . . .
C2 C 0.4964(3) 0.6607(3) 0.68702(17) 0.0425(7) Uani 1 1 d . . . . .
H2 H 0.539551 0.681458 0.731873 0.051 Uiso 1 1 calc R . . . .
C14 C 0.1611(3) 0.8393(2) 0.23389(15) 0.0296(6) Uani 1 1 d . . . . .
C21 C 0.2139(3) 1.1238(3) 0.32857(16) 0.0365(6) Uani 1 1 d . . . . .
H21 H 0.245676 1.150626 0.374697 0.044 Uiso 1 1 calc R . . . .
C15 C 0.1586(2) 0.9667(2) 0.24879(13) 0.0291(5) Uani 1 1 d . . . . .
C5 C 0.3710(2) 0.6028(2) 0.55018(14) 0.0284(5) Uani 1 1 d . . . . .
C3 C 0.4677(3) 0.5432(3) 0.67127(16) 0.0428(7) Uani 1 1 d . . . . .
H3 H 0.488958 0.483711 0.706087 0.051 Uiso 1 1 calc R . . . .
C11 C 0.1768(3) 0.5987(3) 0.20227(16) 0.0452(7) Uani 1 1 d . . . . .
H11 H 0.184877 0.516328 0.193078 0.054 Uiso 1 1 calc R . . . .
C1 C 0.4609(3) 0.7504(3) 0.63545(14) 0.0363(6) Uani 1 1 d . . . . .
H1 H 0.480525 0.830923 0.646178 0.044 Uiso 1 1 calc R . . . .
C19 C 0.1249(3) 1.1726(3) 0.20866(18) 0.0432(7) Uani 1 1 d . . . . .
H19 H 0.097003 1.229129 0.173200 0.052 Uiso 1 1 calc R . . . .
C16 C 0.1130(3) 1.0489(3) 0.19355(14) 0.0358(6) Uani 1 1 d . . . . .
C4 C 0.4056(3) 0.5104(2) 0.60244(15) 0.0344(6) Uani 1 1 d . . . . .
C8 C 0.3139(4) 0.3617(2) 0.5183(2) 0.0453(8) Uani 1 1 d . . . . .
H8 H 0.293276 0.281427 0.507155 0.054 Uiso 1 1 calc R . . . .
C13 C 0.1155(3) 0.7973(3) 0.16347(14) 0.0356(6) Uani 1 1 d . . . . .
C7 C 0.2811(3) 0.4516(2) 0.46708(17) 0.0384(6) Uani 1 1 d . . . . .
H7 H 0.238844 0.429685 0.422210 0.046 Uiso 1 1 calc R . . . .
C20 C 0.1771(3) 1.2098(3) 0.27508(17) 0.0418(7) Uani 1 1 d . . . . .
H20 H 0.188334 1.291776 0.284964 0.050 Uiso 1 1 calc R . . . .
C10 C 0.2183(3) 0.6457(2) 0.27139(18) 0.0389(7) Uani 1 1 d . . . . .
H10 H 0.252930 0.592900 0.307429 0.047 Uiso 1 1 calc R . . . .
C18 C 0.0624(3) 0.8836(4) 0.10975(16) 0.0459(7) Uani 1 1 d . . . . .
H18 H 0.028290 0.856127 0.064193 0.055 Uiso 1 1 calc R . . . .
C12 C 0.1245(3) 0.6739(3) 0.14851(17) 0.0445(7) Uani 1 1 d . . . . .
H12 H 0.095394 0.643469 0.102771 0.053 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Gd1 Cl2 2.6627(7) . ?
Gd1 Cl1 2.6709(8) . ?
Gd1 O2 2.1701(17) . ?
Gd1 O1 2.2291(18) . ?
Gd1 O3 2.4323(17) . ?
Gd1 N3 2.562(2) . ?
Gd1 N2 2.564(2) . ?
O2 C6 1.320(3) . ?
O1 N1 1.323(3) . ?
O3 H3A 0.8645 . ?
O3 H3B 0.8640 . ?
N1 C5 1.386(4) . ?
N1 C1 1.338(3) . ?
N3 C21 1.331(4) . ?
N3 C15 1.365(3) . ?
N2 C14 1.358(3) . ?
N2 C10 1.337(3) . ?
C9 H9 0.9300 . ?
C9 C4 1.397(4) . ?
C9 C8 1.363(5) . ?
C6 C5 1.420(4) . ?
C6 C7 1.390(4) . ?
C17 H17 0.9300 . ?
C17 C16 1.433(4) . ?
C17 C18 1.335(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.357(4) . ?
C2 C1 1.397(4) . ?
C14 C15 1.436(4) . ?
C14 C13 1.415(4) . ?
C21 H21 0.9300 . ?
C21 C20 1.396(4) . ?
C15 C16 1.412(3) . ?
C5 C4 1.426(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.414(4) . ?
C11 H11 0.9300 . ?
C11 C10 1.403(4) . ?
C11 C12 1.365(5) . ?
C1 H1 0.9300 . ?
C19 H19 0.9300 . ?
C19 C16 1.398(4) . ?
C19 C20 1.354(5) . ?
C8 H8 0.9300 . ?
C8 C7 1.390(4) . ?
C13 C18 1.445(4) . ?
C13 C12 1.394(4) . ?
C7 H7 0.9300 . ?
C20 H20 0.9300 . ?
C10 H10 0.9300 . ?
C18 H18 0.9300 . ?
C12 H12 0.9300 . ?

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
Cl2 Gd1 Cl1 161.47(2) . . ?
O2 Gd1 Cl2 105.81(6) . . ?
O2 Gd1 Cl1 92.24(6) . . ?
O2 Gd1 O1 73.97(8) . . ?
O2 Gd1 O3 141.54(7) . . ?
O2 Gd1 N3 138.73(8) . . ?
O2 Gd1 N2 74.67(8) . . ?
O1 Gd1 Cl2 88.47(6) . . ?
O1 Gd1 Cl1 100.80(6) . . ?
O1 Gd1 O3 70.88(7) . . ?
O1 Gd1 N3 147.16(7) . . ?
O1 Gd1 N2 147.38(7) . . ?
O3 Gd1 Cl2 88.51(5) . . ?
O3 Gd1 Cl1 79.60(5) . . ?
O3 Gd1 N3 78.16(6) . . ?
O3 Gd1 N2 141.74(7) . . ?
N3 Gd1 Cl2 79.90(5) . . ?
N3 Gd1 Cl1 83.76(5) . . ?
N3 Gd1 N2 64.24(7) . . ?
N2 Gd1 Cl2 91.57(5) . . ?
N2 Gd1 Cl1 89.14(5) . . ?
C6 O2 Gd1 138.51(18) . . ?
N1 O1 Gd1 138.74(16) . . ?
Gd1 O3 H3A 110.4 . . ?
Gd1 O3 H3B 109.7 . . ?
H3A O3 H3B 103.7 . . ?
O1 N1 C5 122.1(2) . . ?
O1 N1 C1 115.1(2) . . ?
C1 N1 C5 122.8(2) . . ?
C21 N3 Gd1 122.65(18) . . ?
C21 N3 C15 118.0(2) . . ?
C15 N3 Gd1 119.39(16) . . ?
C14 N2 Gd1 119.17(17) . . ?
C10 N2 Gd1 122.95(19) . . ?
C10 N2 C14 117.8(2) . . ?
C4 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C8 C9 C4 120.2(3) . . ?
O2 C6 C5 123.8(2) . . ?
O2 C6 C7 119.3(2) . . ?
C7 C6 C5 116.9(2) . . ?
C16 C17 H17 119.2 . . ?
C18 C17 H17 119.2 . . ?
C18 C17 C16 121.6(3) . . ?
C3 C2 H2 120.2 . . ?
C3 C2 C1 119.6(3) . . ?
C1 C2 H2 120.2 . . ?
N2 C14 C15 118.7(2) . . ?
N2 C14 C13 122.3(2) . . ?
C13 C14 C15 119.0(2) . . ?
N3 C21 H21 118.5 . . ?
N3 C21 C20 123.1(3) . . ?
C20 C21 H21 118.5 . . ?
N3 C15 C14 117.9(2) . . ?
N3 C15 C16 121.7(3) . . ?
C16 C15 C14 120.3(2) . . ?
N1 C5 C6 122.1(2) . . ?
N1 C5 C4 117.3(2) . . ?
C6 C5 C4 120.6(3) . . ?
C2 C3 H3 119.7 . . ?
C2 C3 C4 120.6(3) . . ?
C4 C3 H3 119.7 . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C12 C11 C10 120.0(3) . . ?
N1 C1 C2 120.5(3) . . ?
N1 C1 H1 119.7 . . ?
C2 C1 H1 119.7 . . ?
C16 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C20 C19 C16 119.8(3) . . ?
C15 C16 C17 118.6(3) . . ?
C19 C16 C17 123.4(3) . . ?
C19 C16 C15 117.9(3) . . ?
C9 C4 C5 119.2(3) . . ?
C9 C4 C3 121.7(3) . . ?
C3 C4 C5 119.1(3) . . ?
C9 C8 H8 119.7 . . ?
C9 C8 C7 120.6(3) . . ?
C7 C8 H8 119.7 . . ?
C14 C13 C18 119.0(3) . . ?
C12 C13 C14 118.5(3) . . ?
C12 C13 C18 122.5(3) . . ?
C6 C7 H7 118.8 . . ?
C8 C7 C6 122.5(3) . . ?
C8 C7 H7 118.8 . . ?
C21 C20 H20 120.3 . . ?
C19 C20 C21 119.4(3) . . ?
C19 C20 H20 120.3 . . ?
N2 C10 C11 122.6(3) . . ?
N2 C10 H10 118.7 . . ?
C11 C10 H10 118.7 . . ?
C17 C18 C13 121.2(3) . . ?
C17 C18 H18 119.4 . . ?
C13 C18 H18 119.4 . . ?
C11 C12 C13 118.8(3) . . ?
C11 C12 H12 120.6 . . ?
C13 C12 H12 120.6 . . ?

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
Gd1 O2 C6 C5 -10.2(4) . . . . ?
Gd1 O2 C6 C7 170.7(2) . . . . ?
Gd1 O1 N1 C5 -9.0(4) . . . . ?
Gd1 O1 N1 C1 174.0(2) . . . . ?
Gd1 N3 C21 C20 -179.3(2) . . . . ?
Gd1 N3 C15 C14 -6.3(3) . . . . ?
Gd1 N3 C15 C16 175.88(17) . . . . ?
Gd1 N2 C14 C15 6.5(3) . . . . ?
Gd1 N2 C14 C13 -175.00(19) . . . . ?
Gd1 N2 C10 C11 175.9(2) . . . . ?
O2 C6 C5 N1 3.3(4) . . . . ?
O2 C6 C5 C4 -177.4(2) . . . . ?
O2 C6 C7 C8 177.9(3) . . . . ?
O1 N1 C5 C6 5.1(4) . . . . ?
O1 N1 C5 C4 -174.2(2) . . . . ?
O1 N1 C1 C2 174.8(3) . . . . ?
N1 C5 C4 C9 178.5(2) . . . . ?
N1 C5 C4 C3 -0.9(3) . . . . ?
N3 C21 C20 C19 3.0(4) . . . . ?
N3 C15 C16 C17 -178.3(2) . . . . ?
N3 C15 C16 C19 3.9(4) . . . . ?
N2 C14 C15 N3 -0.2(4) . . . . ?
N2 C14 C15 C16 177.7(2) . . . . ?
N2 C14 C13 C18 178.9(3) . . . . ?
N2 C14 C13 C12 -1.5(4) . . . . ?
C9 C8 C7 C6 -0.2(5) . . . . ?
C6 C5 C4 C9 -0.8(4) . . . . ?
C6 C5 C4 C3 179.8(2) . . . . ?
C2 C3 C4 C9 179.3(3) . . . . ?
C2 C3 C4 C5 -1.3(4) . . . . ?
C14 N2 C10 C11 -0.9(4) . . . . ?
C14 C15 C16 C17 3.9(4) . . . . ?
C14 C15 C16 C19 -173.9(2) . . . . ?
C14 C13 C18 C17 3.1(4) . . . . ?
C14 C13 C12 C11 0.0(4) . . . . ?
C21 N3 C15 C14 174.6(2) . . . . ?
C21 N3 C15 C16 -3.3(4) . . . . ?
C15 N3 C21 C20 -0.1(4) . . . . ?
C15 C14 C13 C18 -2.6(4) . . . . ?
C15 C14 C13 C12 177.0(3) . . . . ?
C5 N1 C1 C2 -2.2(4) . . . . ?
C5 C6 C7 C8 -1.2(4) . . . . ?
C3 C2 C1 N1 -0.1(5) . . . . ?
C1 N1 C5 C6 -178.0(2) . . . . ?
C1 N1 C5 C4 2.6(3) . . . . ?
C1 C2 C3 C4 1.8(5) . . . . ?
C16 C17 C18 C13 0.1(5) . . . . ?
C16 C19 C20 C21 -2.3(4) . . . . ?
C4 C9 C8 C7 1.1(4) . . . . ?
C8 C9 C4 C5 -0.6(4) . . . . ?
C8 C9 C4 C3 178.7(3) . . . . ?
C13 C14 C15 N3 -178.7(2) . . . . ?
C13 C14 C15 C16 -0.8(4) . . . . ?
C7 C6 C5 N1 -177.6(2) . . . . ?
C7 C6 C5 C4 1.7(4) . . . . ?
C20 C19 C16 C17 -178.7(3) . . . . ?
C20 C19 C16 C15 -1.0(4) . . . . ?
C10 N2 C14 C15 -176.6(3) . . . . ?
C10 N2 C14 C13 1.9(4) . . . . ?
C10 C11 C12 C13 1.0(5) . . . . ?
C18 C17 C16 C15 -3.6(4) . . . . ?
C18 C17 C16 C19 174.1(3) . . . . ?
C18 C13 C12 C11 179.6(3) . . . . ?
C12 C11 C10 N2 -0.6(5) . . . . ?
C12 C13 C18 C17 -176.5(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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 2050204'
_audit_update_record             
;
2020-12-14 deposited with the CCDC.	2021-03-26 downloaded from the CCDC.
;
_audit_creation_date             2019-05-17
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.06 svn.r2239, GUI svn.r4109)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C21 H16 Cl2 Dy N3 O3'
_chemical_formula_sum            'C21 H16 Cl2 Dy N3 O3'
_chemical_formula_weight         591.77
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1'
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'
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'
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 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.8681(4)
_cell_length_b                   11.0471(4)
_cell_length_c                   18.2005(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.009(3)
_cell_angle_gamma                90
_cell_volume                     1981.36(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3573
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.0290
_cell_measurement_theta_min      3.6690
_exptl_absorpt_coefficient_mu    4.071
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.984
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1148
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0424
_diffrn_reflns_av_unetI/netI     0.0449
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12454
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         3.495
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0233
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9967
_diffrn_measured_fraction_theta_max 0.8848
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω     21.00  61.00   1.00    1.50    --   18.78 -99.00   0.00   40
  2  ω    -86.00   9.00   1.00    1.50    --  -19.10 -77.00  90.00   95
  3  ω    -25.00   1.00   1.00    1.50    --  -19.10 -57.00-150.00   26
  4  ω    -48.00  48.00   1.00    1.50    --  -19.10  77.00-150.00   96
  5  ω    -54.00  43.00   1.00    1.50    --  -19.10  19.00  30.00   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0382444000
_diffrn_orient_matrix_UB_12      0.0540001000
_diffrn_orient_matrix_UB_13      0.0052508000
_diffrn_orient_matrix_UB_21      -0.0560699000
_diffrn_orient_matrix_UB_22      0.0343351000
_diffrn_orient_matrix_UB_23      -0.0143287000
_diffrn_orient_matrix_UB_31      -0.0238919000
_diffrn_orient_matrix_UB_32      0.0057263000
_diffrn_orient_matrix_UB_33      0.0359048000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_current           n/a
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_source_voltage           n/a
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3254
_reflns_number_total             4054
_reflns_odcompleteness_completeness 99.67
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELXL, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELXS, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         1.717
_refine_diff_density_min         -1.136
_refine_diff_density_rms         0.132
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.117
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4054
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0494
_refine_ls_R_factor_gt           0.0338
_refine_ls_restrained_S_all      1.117
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0298P)²+2.2449P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0733
_refine_ls_wR_factor_ref         0.0842
_refine_special_details          
;
 ?
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Dy1 Dy 0.72897(2) 0.65153(2) 0.08400(2) 0.02807(10) Uani 1 1 d . . . . .
Cl1 Cl 0.99220(14) 0.64422(14) 0.05867(8) 0.0440(4) Uani 1 1 d . . . . .
Cl2 Cl 0.48412(14) 0.58590(13) 0.12347(7) 0.0392(3) Uani 1 1 d . . . . .
O1 O 0.7385(4) 0.4675(3) 0.01180(18) 0.0379(9) Uani 1 1 d . . . . .
H1A H 0.8159 0.4255 0.0023 0.057 Uiso 1 1 d R U . . .
H1B H 0.6652 0.4285 -0.0104 0.057 Uiso 1 1 d R U . . .
O2 O 0.6398(4) 0.6854(3) -0.02883(19) 0.0429(10) Uani 1 1 d . . . . .
O3 O 0.7212(4) 0.8462(3) 0.07112(19) 0.0377(9) Uani 1 1 d . . . . .
N1 N 0.7934(4) 0.4945(4) 0.1829(2) 0.0329(10) Uani 1 1 d . . . . .
N2 N 0.7903(4) 0.7370(4) 0.2124(2) 0.0333(10) Uani 1 1 d . . . . .
N3 N 0.6010(4) 0.7787(4) -0.0710(2) 0.0320(10) Uani 1 1 d . . . . .
C1 C 0.5393(5) 0.7489(6) -0.1357(3) 0.0395(13) Uani 1 1 d . . . . .
H1 H 0.5198 0.6683 -0.1465 0.047 Uiso 1 1 calc R U . . .
C2 C 0.5041(6) 0.8392(6) -0.1870(3) 0.0448(15) Uani 1 1 d . . . . .
H2 H 0.4617 0.8187 -0.2321 0.054 Uiso 1 1 calc R U . . .
C3 C 0.5318(5) 0.9569(6) -0.1710(3) 0.0446(15) Uani 1 1 d . . . . .
H3 H 0.5092 1.0167 -0.2054 0.054 Uiso 1 1 calc R U . . .
C4 C 0.5946(5) 0.9888(5) -0.1026(3) 0.0374(13) Uani 1 1 d . . . . .
C5 C 0.6277(5) 0.8963(5) -0.0507(3) 0.0290(11) Uani 1 1 d . . . . .
C6 C 0.6916(5) 0.9268(5) 0.0197(3) 0.0319(12) Uani 1 1 d . . . . .
C7 C 0.7179(6) 1.0471(5) 0.0336(3) 0.0434(14) Uani 1 1 d . . . . .
H7 H 0.7577 1.0686 0.0792 0.052 Uiso 1 1 calc R U . . .
C8 C 0.6874(7) 1.1387(5) -0.0179(4) 0.0480(16) Uani 1 1 d . . . . .
H8 H 0.7098 1.2187 -0.0069 0.058 Uiso 1 1 calc R U . . .
C9 C 0.6239(6) 1.1098(6) -0.0850(4) 0.0489(16) Uani 1 1 d . . . . .
H9 H 0.6006 1.1708 -0.1186 0.059 Uiso 1 1 calc R U . . .
C10 C 0.7859(6) 0.8527(5) 0.2311(3) 0.0396(14) Uani 1 1 d . . . . .
H10 H 0.7543 0.9064 0.1947 0.047 Uiso 1 1 calc R U . . .
C11 C 0.8228(6) 0.9014(6) 0.2978(3) 0.0443(15) Uani 1 1 d . . . . .
H11 H 0.8122 0.9837 0.3066 0.053 Uiso 1 1 calc R U . . .
C12 C 0.8757(6) 0.8266(6) 0.3513(3) 0.0452(15) Uani 1 1 d . . . . .
H12 H 0.9055 0.8575 0.3968 0.054 Uiso 1 1 calc R U . . .
C13 C 0.8846(5) 0.7034(6) 0.3370(3) 0.0385(13) Uani 1 1 d . . . . .
C14 C 0.9368(6) 0.6157(7) 0.3901(3) 0.0502(17) Uani 1 1 d . . . . .
H14 H 0.9703 0.6427 0.4360 0.060 Uiso 1 1 calc R U . . .
C15 C 0.9386(6) 0.4972(7) 0.3757(3) 0.0481(16) Uani 1 1 d . . . . .
H15 H 0.9736 0.4437 0.4113 0.058 Uiso 1 1 calc R U . . .
C16 C 0.8872(5) 0.4515(6) 0.3059(3) 0.0396(13) Uani 1 1 d . . . . .
C17 C 0.8733(6) 0.3279(6) 0.2917(3) 0.0452(15) Uani 1 1 d . . . . .
H17 H 0.8980 0.2716 0.3280 0.054 Uiso 1 1 calc R U . . .
C18 C 0.8233(6) 0.2906(6) 0.2245(3) 0.0442(14) Uani 1 1 d . . . . .
H18 H 0.8144 0.2086 0.2138 0.053 Uiso 1 1 calc R U . . .
C19 C 0.7858(6) 0.3771(5) 0.1721(3) 0.0395(13) Uani 1 1 d . . . . .
H19 H 0.7531 0.3501 0.1261 0.047 Uiso 1 1 calc R U . . .
C20 C 0.8405(5) 0.5327(5) 0.2510(2) 0.0300(11) Uani 1 1 d . . . . .
C21 C 0.8397(5) 0.6603(5) 0.2663(3) 0.0309(12) 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
Dy1 Cl1 2.6631(14) . ?
Dy1 Cl2 2.6574(14) . ?
Dy1 O1 2.425(3) . ?
Dy1 O2 2.223(3) . ?
Dy1 O3 2.164(3) . ?
Dy1 N1 2.556(4) . ?
Dy1 N2 2.563(4) . ?
O2 N3 1.330(5) . ?
O3 C6 1.314(6) . ?
N1 C19 1.314(7) . ?
N1 C20 1.367(6) . ?
N2 C10 1.325(6) . ?
N2 C21 1.368(6) . ?
N3 C1 1.338(6) . ?
N3 C5 1.372(7) . ?
C1 C2 1.398(8) . ?
C2 C3 1.357(8) . ?
C3 C4 1.405(8) . ?
C4 C5 1.418(7) . ?
C4 C9 1.402(8) . ?
C5 C6 1.437(7) . ?
C6 C7 1.375(8) . ?
C7 C8 1.401(8) . ?
C8 C9 1.381(9) . ?
C10 C11 1.360(7) . ?
C11 C12 1.360(8) . ?
C12 C13 1.389(8) . ?
C13 C14 1.445(8) . ?
C13 C21 1.420(7) . ?
C14 C15 1.336(9) . ?
C15 C16 1.433(8) . ?
C16 C17 1.395(8) . ?
C16 C20 1.403(7) . ?
C17 C18 1.360(8) . ?
C18 C19 1.386(7) . ?
C20 C21 1.436(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl2 Dy1 Cl1 161.35(5) . . ?
O1 Dy1 Cl1 79.32(9) . . ?
O1 Dy1 Cl2 88.83(9) . . ?
O1 Dy1 N1 78.32(12) . . ?
O1 Dy1 N2 142.06(13) . . ?
O2 Dy1 Cl1 100.81(12) . . ?
O2 Dy1 Cl2 88.52(11) . . ?
O2 Dy1 O1 70.45(13) . . ?
O2 Dy1 N1 146.78(14) . . ?
O2 Dy1 N2 147.49(14) . . ?
O3 Dy1 Cl1 92.33(11) . . ?
O3 Dy1 Cl2 105.84(11) . . ?
O3 Dy1 O1 140.94(12) . . ?
O3 Dy1 O2 73.90(13) . . ?
O3 Dy1 N1 139.16(14) . . ?
O3 Dy1 N2 74.81(13) . . ?
N1 Dy1 Cl1 83.84(10) . . ?
N1 Dy1 Cl2 79.65(10) . . ?
N1 Dy1 N2 64.51(14) . . ?
N2 Dy1 Cl1 89.03(10) . . ?
N2 Dy1 Cl2 91.64(10) . . ?
N3 O2 Dy1 138.7(3) . . ?
C6 O3 Dy1 139.1(3) . . ?
C19 N1 Dy1 123.6(3) . . ?
C19 N1 C20 117.1(4) . . ?
C20 N1 Dy1 119.3(3) . . ?
C10 N2 Dy1 125.5(4) . . ?
C10 N2 C21 115.4(5) . . ?
C21 N2 Dy1 119.0(3) . . ?
O2 N3 C1 114.9(4) . . ?
O2 N3 C5 122.3(4) . . ?
C1 N3 C5 122.8(4) . . ?
N3 C1 C2 119.8(6) . . ?
C3 C2 C1 120.0(5) . . ?
C2 C3 C4 120.3(5) . . ?
C3 C4 C5 119.0(5) . . ?
C9 C4 C3 121.2(5) . . ?
C9 C4 C5 119.8(5) . . ?
N3 C5 C4 117.9(5) . . ?
N3 C5 C6 122.0(4) . . ?
C4 C5 C6 120.0(5) . . ?
O3 C6 C5 123.1(5) . . ?
O3 C6 C7 119.4(5) . . ?
C7 C6 C5 117.4(5) . . ?
C6 C7 C8 122.9(6) . . ?
C9 C8 C7 119.8(6) . . ?
C8 C9 C4 120.1(5) . . ?
N2 C10 C11 126.9(6) . . ?
C12 C11 C10 118.2(6) . . ?
C11 C12 C13 119.2(5) . . ?
C12 C13 C14 123.7(5) . . ?
C12 C13 C21 118.6(5) . . ?
C21 C13 C14 117.7(6) . . ?
C15 C14 C13 122.2(6) . . ?
C14 C15 C16 120.8(6) . . ?
C17 C16 C15 122.4(5) . . ?
C17 C16 C20 117.9(5) . . ?
C20 C16 C15 119.6(6) . . ?
C18 C17 C16 119.4(5) . . ?
C17 C18 C19 118.8(6) . . ?
N1 C19 C18 124.5(5) . . ?
N1 C20 C16 122.1(5) . . ?
N1 C20 C21 118.3(4) . . ?
C16 C20 C21 119.6(5) . . ?
N2 C21 C13 121.6(5) . . ?
N2 C21 C20 118.2(4) . . ?
C13 C21 C20 120.1(5) . . ?

_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.644
_oxdiff_exptl_absorpt_empirical_full_min 0.746
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?

####################################################################### 
# 
# 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_62
_database_code_depnum_ccdc_archive 'CCDC 2050202'
_audit_update_record             
;
2020-12-14 deposited with the CCDC.	2021-03-26 downloaded from the CCDC.
;
_audit_creation_date             2019-09-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C21 H16 Cl2 N3 O3 Yb'
_chemical_formula_sum            'C21 H16 Cl2 N3 O3 Yb'
_chemical_formula_weight         602.31
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
Yb Yb -0.3850 5.5486 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.87834(18)
_cell_length_b                   11.02546(19)
_cell_length_c                   18.1528(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.2424(15)
_cell_angle_gamma                90
_cell_volume                     1973.92(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5642
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.6270
_cell_measurement_theta_min      3.6730
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.038
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    2.027
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1164
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0444
_diffrn_reflns_av_unetI/netI     0.0509
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.884
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            13881
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.884
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.176
_diffrn_reflns_theta_min         3.494
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.0233
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.884
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     21.00  61.00   1.00    3.50    --   18.63 -99.00-120.00   40
  2  ω    -89.00   9.00   1.00    3.50    --  -18.94 -77.00 -30.00   98
  3  ω    -25.00   1.00   1.00    3.50    --  -18.94 -57.00  90.00   26
  4  ω    -46.00  43.00   1.00    3.50    --  -18.94  77.00  90.00   89
  5  ω    -89.00   9.00   1.00    3.50    --  -18.94 -19.00 150.00   98
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0693083000
_diffrn_orient_matrix_UB_12      -0.0165707000
_diffrn_orient_matrix_UB_13      0.0004206000
_diffrn_orient_matrix_UB_21      -0.0177907000
_diffrn_orient_matrix_UB_22      0.0500807000
_diffrn_orient_matrix_UB_23      -0.0231090000
_diffrn_orient_matrix_UB_31      0.0070016000
_diffrn_orient_matrix_UB_32      -0.0368533000
_diffrn_orient_matrix_UB_33      -0.0315865000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3820
_reflns_number_total             4716
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.154
_refine_diff_density_min         -0.919
_refine_diff_density_rms         0.145
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     272
_refine_ls_number_reflns         4716
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0450
_refine_ls_R_factor_gt           0.0315
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0233P)²+0.0423P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0617
_refine_ls_wR_factor_ref         0.0689
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Rotating group:
 O1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C7(H7), C9(H9), C10(H10), C11(H11),
 C13(H13), C14(H14), C16(H16), C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     heavy
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Yb1 Yb 0.76987(2) 0.65099(2) 0.41646(2) 0.02296(7) Uani 1 1 d . . . . .
Cl1 Cl 1.01196(10) 0.58861(10) 0.37822(6) 0.0323(2) Uani 1 1 d . . . . .
Cl2 Cl 0.51023(11) 0.64484(11) 0.44135(6) 0.0379(3) Uani 1 1 d . . . . .
O1 O 0.7624(3) 0.4677(3) 0.48648(14) 0.0313(7) Uani 1 1 d . . . . .
H1A H 0.6836 0.4594 0.5073 0.047 Uiso 1 1 d GR . . . .
H1B H 0.8215 0.4699 0.5252 0.047 Uiso 1 1 d GR . . . .
O2 O 0.8578(3) 0.6822(3) 0.52857(16) 0.0381(8) Uani 1 1 d . . . . .
O3 O 0.7773(3) 0.8435(2) 0.42905(16) 0.0346(8) Uani 1 1 d . . . . .
N1 N 0.7062(3) 0.4942(3) 0.31922(18) 0.0259(8) Uani 1 1 d . . . . .
N2 N 0.7111(3) 0.7368(3) 0.29000(18) 0.0277(8) Uani 1 1 d . . . . .
N3 N 0.8977(3) 0.7745(3) 0.57084(18) 0.0270(8) Uani 1 1 d . . . . .
C1 C 0.9605(4) 0.7454(4) 0.6360(2) 0.0294(10) Uani 1 1 d . . . . .
H1 H 0.9801 0.6647 0.6469 0.035 Uiso 1 1 calc R . . . .
C2 C 0.9963(5) 0.8350(5) 0.6875(2) 0.0393(12) Uani 1 1 d . . . . .
H2 H 1.0399 0.8141 0.7325 0.047 Uiso 1 1 calc R . . . .
C3 C 0.9675(4) 0.9532(4) 0.6719(2) 0.0364(11) Uani 1 1 d . . . . .
H3 H 0.9889 1.0126 0.7070 0.044 Uiso 1 1 calc R . . . .
C4 C 0.9060(4) 0.9863(4) 0.6036(2) 0.0295(10) Uani 1 1 d . . . . .
C5 C 0.8766(5) 1.1078(4) 0.5858(3) 0.0386(12) Uani 1 1 d . . . . .
H5 H 0.8995 1.1689 0.6195 0.046 Uiso 1 1 calc R . . . .
C5AA C 0.8710(4) 0.8947(4) 0.5506(2) 0.0251(9) Uani 1 1 d . . . . .
C6 C 0.8144(5) 1.1360(4) 0.5190(3) 0.0399(12) Uani 1 1 d . . . . .
H6 H 0.7943 1.2165 0.5078 0.048 Uiso 1 1 calc R . . . .
C7 C 0.7804(4) 1.0457(4) 0.4671(2) 0.0332(10) Uani 1 1 d . . . . .
H7 H 0.7383 1.0680 0.4220 0.040 Uiso 1 1 calc R . . . .
C8 C 0.8075(4) 0.9246(4) 0.4806(2) 0.0245(9) Uani 1 1 d . . . . .
C9 C 0.7185(5) 0.8537(4) 0.2722(3) 0.0339(11) Uani 1 1 d . . . . .
H9 H 0.7526 0.9070 0.3083 0.041 Uiso 1 1 calc R . . . .
C10 C 0.6792(5) 0.9017(4) 0.2038(2) 0.0389(12) Uani 1 1 d . . . . .
H10 H 0.6892 0.9841 0.1946 0.047 Uiso 1 1 calc R . . . .
C11 C 0.6256(4) 0.8261(5) 0.1501(2) 0.0376(12) Uani 1 1 d . . . . .
H11 H 0.5958 0.8569 0.1043 0.045 Uiso 1 1 calc R . . . .
C12 C 0.6162(4) 0.7027(4) 0.1647(2) 0.0300(10) Uani 1 1 d . . . . .
C13 C 0.5626(4) 0.6161(5) 0.1109(2) 0.0413(13) Uani 1 1 d . . . . .
H13 H 0.5277 0.6438 0.0653 0.050 Uiso 1 1 calc R . . . .
C14 C 0.5619(4) 0.4976(5) 0.1251(2) 0.0395(12) Uani 1 1 d . . . . .
H14 H 0.5280 0.4441 0.0890 0.047 Uiso 1 1 calc R . . . .
C15 C 0.6128(4) 0.4513(5) 0.1951(2) 0.0307(10) Uani 1 1 d . . . . .
C16 C 0.6261(4) 0.3260(5) 0.2105(3) 0.0384(12) Uani 1 1 d . . . . .
H16 H 0.5995 0.2690 0.1748 0.046 Uiso 1 1 calc R . . . .
C17 C 0.6777(4) 0.2896(4) 0.2775(2) 0.0365(11) Uani 1 1 d . . . . .
H17 H 0.6880 0.2074 0.2879 0.044 Uiso 1 1 calc R . . . .
C18 C 0.7149(4) 0.3756(4) 0.3304(2) 0.0328(10) Uani 1 1 d . . . . .
H18 H 0.7480 0.3486 0.3765 0.039 Uiso 1 1 calc R . . . .
C19 C 0.6596(4) 0.5315(4) 0.2512(2) 0.0247(9) Uani 1 1 d . . . . .
C20 C 0.6615(4) 0.6601(4) 0.2356(2) 0.0256(9) 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
Yb1 Cl1 2.6194(10) . ?
Yb1 Cl2 2.6302(11) . ?
Yb1 O1 2.391(3) . ?
Yb1 O2 2.194(3) . ?
Yb1 O3 2.136(3) . ?
Yb1 N1 2.524(3) . ?
Yb1 N2 2.520(3) . ?
O2 N3 1.321(4) . ?
O3 C8 1.316(5) . ?
N1 C18 1.326(5) . ?
N1 C19 1.357(5) . ?
N2 C9 1.332(5) . ?
N2 C20 1.369(5) . ?
N3 C1 1.343(5) . ?
N3 C5AA 1.396(5) . ?
C1 C2 1.391(6) . ?
C2 C3 1.361(6) . ?
C3 C4 1.398(6) . ?
C4 C5 1.405(6) . ?
C4 C5AA 1.423(5) . ?
C5 C6 1.364(7) . ?
C5AA C8 1.425(6) . ?
C6 C7 1.399(6) . ?
C7 C8 1.381(6) . ?
C9 C10 1.383(6) . ?
C10 C11 1.368(6) . ?
C11 C12 1.390(6) . ?
C12 C13 1.444(6) . ?
C12 C20 1.419(6) . ?
C13 C14 1.332(7) . ?
C14 C15 1.434(6) . ?
C15 C16 1.414(6) . ?
C15 C19 1.407(5) . ?
C16 C17 1.352(6) . ?
C17 C18 1.385(6) . ?
C19 C20 1.447(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Yb1 Cl2 162.27(4) . . ?
O1 Yb1 Cl1 88.57(7) . . ?
O1 Yb1 Cl2 80.05(7) . . ?
O1 Yb1 N1 77.24(10) . . ?
O1 Yb1 N2 142.10(10) . . ?
O2 Yb1 Cl1 88.15(9) . . ?
O2 Yb1 Cl2 100.56(9) . . ?
O2 Yb1 O1 70.25(10) . . ?
O2 Yb1 N1 145.68(11) . . ?
O2 Yb1 N2 147.64(11) . . ?
O3 Yb1 Cl1 105.23(9) . . ?
O3 Yb1 Cl2 92.03(9) . . ?
O3 Yb1 O1 141.73(10) . . ?
O3 Yb1 O2 74.65(11) . . ?
O3 Yb1 N1 139.55(11) . . ?
O3 Yb1 N2 74.29(11) . . ?
N1 Yb1 Cl1 80.21(8) . . ?
N1 Yb1 Cl2 84.01(8) . . ?
N2 Yb1 Cl1 91.38(8) . . ?
N2 Yb1 Cl2 89.39(8) . . ?
N2 Yb1 N1 65.45(11) . . ?
N3 O2 Yb1 138.5(2) . . ?
C8 O3 Yb1 139.2(3) . . ?
C18 N1 Yb1 123.8(3) . . ?
C18 N1 C19 117.0(4) . . ?
C19 N1 Yb1 119.2(3) . . ?
C9 N2 Yb1 124.9(3) . . ?
C9 N2 C20 116.4(4) . . ?
C20 N2 Yb1 118.7(3) . . ?
O2 N3 C1 115.9(4) . . ?
O2 N3 C5AA 122.1(3) . . ?
C1 N3 C5AA 121.9(4) . . ?
N3 C1 C2 120.6(4) . . ?
C3 C2 C1 119.9(4) . . ?
C2 C3 C4 120.6(4) . . ?
C3 C4 C5 121.8(4) . . ?
C3 C4 C5AA 119.4(4) . . ?
C5 C4 C5AA 118.9(4) . . ?
C6 C5 C4 119.9(4) . . ?
N3 C5AA C4 117.4(4) . . ?
N3 C5AA C8 121.5(4) . . ?
C4 C5AA C8 121.1(4) . . ?
C5 C6 C7 121.0(4) . . ?
C8 C7 C6 122.1(4) . . ?
O3 C8 C5AA 123.2(4) . . ?
O3 C8 C7 119.8(4) . . ?
C7 C8 C5AA 117.0(4) . . ?
N2 C9 C10 124.9(5) . . ?
C11 C10 C9 119.0(5) . . ?
C10 C11 C12 119.2(4) . . ?
C11 C12 C13 123.0(4) . . ?
C11 C12 C20 118.4(4) . . ?
C20 C12 C13 118.6(4) . . ?
C14 C13 C12 121.6(4) . . ?
C13 C14 C15 121.0(4) . . ?
C16 C15 C14 123.2(4) . . ?
C19 C15 C14 120.2(4) . . ?
C19 C15 C16 116.6(4) . . ?
C17 C16 C15 119.6(4) . . ?
C16 C17 C18 119.5(5) . . ?
N1 C18 C17 123.8(4) . . ?
N1 C19 C15 123.3(4) . . ?
N1 C19 C20 117.9(4) . . ?
C15 C19 C20 118.8(4) . . ?
N2 C20 C12 122.1(4) . . ?
N2 C20 C19 118.1(4) . . ?
C12 C20 C19 119.7(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.284
_oxdiff_exptl_absorpt_empirical_full_min 0.836
