# Electronic Supplementary Material (ESI) for Materials Advances.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2091656'
_audit_update_record             
;
2021-06-23 deposited with the CCDC.	2021-11-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'Yttrium-organic Compound'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H9 N2 O7.33 Y0.33'
_chemical_formula_weight         292.15

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Y Y -2.7962 3.5667 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           147
_space_group_name_H-M_alt        'P -3'
_space_group_name_Hall           '-P 3'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'

_cell_length_a                   14.8692(13)
_cell_length_b                   14.8692(13)
_cell_length_c                   10.1692(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     1947.1(4)
_cell_formula_units_Z            6
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    2860
_cell_measurement_theta_min      2.552
_cell_measurement_theta_max      27.109

_exptl_crystal_description       'Yellowsih Brown'
_exptl_crystal_colour            'Block Shaped'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.495
_exptl_crystal_F_000             892
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.010
_exptl_absorpt_coefficient_mu    1.588
_shelx_estimated_absorpt_T_min   0.870
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.870
_exptl_absorpt_correction_T_max  0.984
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker SMART CCD area detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            69840
_diffrn_reflns_av_unetI/netI     0.0144
_diffrn_reflns_av_R_equivalents  0.0472
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.552
_diffrn_reflns_theta_max         27.109
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2860
_reflns_number_gt                2676
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       'SAINT (Bruker, 2000)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'Ortep-3 for Windows (Farrugia, 1999) and CAMERON (Watkin et al., 1993)'
_computing_publication_material  'PLATON (Spek, 2003)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0789P)²+1.6303P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2860
_refine_ls_number_parameters     169
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0458
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1432
_refine_ls_wR_factor_gt          0.1412
_refine_ls_goodness_of_fit_ref   1.197
_refine_ls_restrained_S_all      1.197
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Y1 Y 0.333333 0.666667 0.56597(4) 0.02583(17) Uani 1 3 d S T P . .
O1 O 0.45716(16) 0.68340(16) 0.7292(2) 0.0354(5) Uani 1 1 d . . . . .
O3 O 0.35002(17) 0.78970(17) 0.4004(2) 0.0391(5) Uani 1 1 d . . . . .
N1 N 0.50359(18) 0.83023(18) 0.5588(2) 0.0289(5) Uani 1 1 d . . . . .
O4 O 0.4484(2) 0.9269(2) 0.2742(2) 0.0553(7) Uani 1 1 d . . . . .
O2 O 0.6036(2) 0.77560(19) 0.8412(3) 0.0507(6) Uani 1 1 d . . . . .
N2 N 0.3961(2) 0.9148(2) 0.0106(3) 0.0434(6) Uani 1 1 d . . . . .
H2A H 0.391519 0.900040 0.095965 0.052 Uiso 1 1 calc R U . . .
H2B H 0.335499 0.870797 -0.026463 0.052 Uiso 1 1 calc R U . . .
C2 C 0.5785(2) 0.8467(2) 0.6449(3) 0.0317(6) Uani 1 1 d . . . . .
C1 C 0.5440(2) 0.7619(2) 0.7470(3) 0.0327(6) Uani 1 1 d . . . . .
C6 C 0.5248(2) 0.8977(2) 0.4610(3) 0.0331(6) Uani 1 1 d . . . . .
C7 C 0.4340(3) 0.8697(2) 0.3702(3) 0.0359(6) Uani 1 1 d . . . . .
C5 C 0.6221(3) 0.9841(3) 0.4445(3) 0.0469(8) Uani 1 1 d . . . . .
H5 H 0.635284 1.029902 0.375179 0.056 Uiso 1 1 calc R U . . .
C8 C 0.4787(3) 0.8999(3) -0.0488(3) 0.0438(7) Uani 1 1 d . . . . .
H8A H 0.478991 0.908545 -0.143418 0.053 Uiso 1 1 calc R U . . .
H8B H 0.464683 0.830000 -0.031075 0.053 Uiso 1 1 calc R U . . .
C3 C 0.6775(3) 0.9318(3) 0.6365(4) 0.0458(8) Uani 1 1 d . . . . .
H3 H 0.727949 0.942407 0.698299 0.055 Uiso 1 1 calc R U . . .
C9 C 0.4164(3) 1.0227(3) -0.0065(3) 0.0441(7) Uani 1 1 d . . . . .
H9A H 0.362834 1.030143 0.038073 0.053 Uiso 1 1 calc R U . . .
H9B H 0.414057 1.036585 -0.099213 0.053 Uiso 1 1 calc R U . . .
O200 O 0.333333 0.666667 0.1295(7) 0.115(3) Uani 1 3 d S T P . .
C4 C 0.6994(3) 1.0008(3) 0.5337(4) 0.0557(9) Uani 1 1 d . . . . .
H4 H 0.765705 1.057994 0.524567 0.067 Uiso 1 1 calc R U . . .
O300 O 0.2131(3) 0.7954(4) 0.1949(4) 0.1148(17) Uani 1 1 d . . . . .
O100 O 0.7940(6) 0.8918(7) 0.9487(12) 0.231(5) Uani 1 1 d . . . . .
O400 O 0.8586(15) 0.8025(10) 0.7993(14) 0.370(10) 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
Y1 O1 2.397(2) 2_665 ?
Y1 O1 2.397(2) 3_565 ?
Y1 O1 2.397(2) . ?
Y1 O3 2.406(2) . ?
Y1 O3 2.406(2) 2_665 ?
Y1 O3 2.406(2) 3_565 ?
Y1 N1 2.484(2) . ?
Y1 N1 2.484(2) 2_665 ?
Y1 N1 2.484(2) 3_565 ?
O1 C1 1.247(4) . ?
O3 C7 1.258(4) . ?
N1 C6 1.333(3) . ?
N1 C2 1.339(4) . ?
O4 C7 1.241(4) . ?
O2 C1 1.251(4) . ?
N2 C8 1.481(5) . ?
N2 C9 1.487(4) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
C2 C3 1.383(4) . ?
C2 C1 1.511(4) . ?
C6 C5 1.383(4) . ?
C6 C7 1.512(4) . ?
C5 C4 1.387(6) . ?
C5 H5 0.9300 . ?
C8 C9 1.509(5) 4_675 ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C3 C4 1.384(5) . ?
C3 H3 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C4 H4 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
O1 Y1 O1 77.36(8) 2_665 3_565 ?
O1 Y1 O1 77.36(8) 2_665 . ?
O1 Y1 O1 77.36(8) 3_565 . ?
O1 Y1 O3 89.14(8) 2_665 . ?
O1 Y1 O3 147.64(7) 3_565 . ?
O1 Y1 O3 128.58(7) . . ?
O1 Y1 O3 128.58(7) 2_665 2_665 ?
O1 Y1 O3 89.14(8) 3_565 2_665 ?
O1 Y1 O3 147.64(7) . 2_665 ?
O3 Y1 O3 76.43(9) . 2_665 ?
O1 Y1 O3 147.64(8) 2_665 3_565 ?
O1 Y1 O3 128.58(7) 3_565 3_565 ?
O1 Y1 O3 89.14(8) . 3_565 ?
O3 Y1 O3 76.43(9) . 3_565 ?
O3 Y1 O3 76.43(9) 2_665 3_565 ?
O1 Y1 N1 76.31(7) 2_665 . ?
O1 Y1 N1 137.09(8) 3_565 . ?
O1 Y1 N1 64.20(7) . . ?
O3 Y1 N1 64.41(7) . . ?
O3 Y1 N1 133.68(8) 2_665 . ?
O3 Y1 N1 71.34(7) 3_565 . ?
O1 Y1 N1 64.21(7) 2_665 2_665 ?
O1 Y1 N1 76.31(7) 3_565 2_665 ?
O1 Y1 N1 137.09(7) . 2_665 ?
O3 Y1 N1 71.34(7) . 2_665 ?
O3 Y1 N1 64.41(7) 2_665 2_665 ?
O3 Y1 N1 133.68(8) 3_565 2_665 ?
N1 Y1 N1 119.915(6) . 2_665 ?
O1 Y1 N1 137.09(7) 2_665 3_565 ?
O1 Y1 N1 64.21(7) 3_565 3_565 ?
O1 Y1 N1 76.31(7) . 3_565 ?
O3 Y1 N1 133.68(8) . 3_565 ?
O3 Y1 N1 71.34(7) 2_665 3_565 ?
O3 Y1 N1 64.41(7) 3_565 3_565 ?
N1 Y1 N1 119.916(6) . 3_565 ?
N1 Y1 N1 119.915(6) 2_665 3_565 ?
C1 O1 Y1 125.43(18) . . ?
C7 O3 Y1 124.45(19) . . ?
C6 N1 C2 119.2(2) . . ?
C6 N1 Y1 120.00(19) . . ?
C2 N1 Y1 120.47(18) . . ?
C8 N2 C9 112.1(3) . . ?
C8 N2 H2A 109.2 . . ?
C9 N2 H2A 109.2 . . ?
C8 N2 H2B 109.2 . . ?
C9 N2 H2B 109.2 . . ?
H2A N2 H2B 107.9 . . ?
N1 C2 C3 122.3(3) . . ?
N1 C2 C1 113.1(2) . . ?
C3 C2 C1 124.6(3) . . ?
O1 C1 O2 125.6(3) . . ?
O1 C1 C2 116.2(2) . . ?
O2 C1 C2 118.2(3) . . ?
N1 C6 C5 122.3(3) . . ?
N1 C6 C7 114.0(3) . . ?
C5 C6 C7 123.8(3) . . ?
O4 C7 O3 126.1(3) . . ?
O4 C7 C6 117.9(3) . . ?
O3 C7 C6 116.0(2) . . ?
C6 C5 C4 118.4(3) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
N2 C8 C9 110.6(3) . 4_675 ?
N2 C8 H8A 109.5 . . ?
C9 C8 H8A 109.5 4_675 . ?
N2 C8 H8B 109.5 . . ?
C9 C8 H8B 109.5 4_675 . ?
H8A C8 H8B 108.1 . . ?
C2 C3 C4 118.3(3) . . ?
C2 C3 H3 120.9 . . ?
C4 C3 H3 120.9 . . ?
N2 C9 C8 110.8(3) . 4_675 ?
N2 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 4_675 . ?
N2 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 4_675 . ?
H9A C9 H9B 108.1 . . ?
C3 C4 C5 119.6(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?

_refine_diff_density_max         0.842
_refine_diff_density_min         -0.457
_refine_diff_density_rms         0.088

