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

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

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 2173536'
_audit_update_record             
;
2022-05-18 deposited with the CCDC.	2022-06-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            'Gadolinium-Organic Compound'
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H4.50 Gd N1.50 O14'
_chemical_formula_weight         538.91

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'

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

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

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

_cell_length_a                   20.0564(16)
_cell_length_b                   10.9978(8)
_cell_length_c                   17.5059(13)
_cell_angle_alpha                90
_cell_angle_beta                 111.797(2)
_cell_angle_gamma                90
_cell_volume                     3585.3(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    3948
_cell_measurement_theta_min      2.151
_cell_measurement_theta_max      27.137

_exptl_crystal_description       Block-shaped
_exptl_crystal_colour            White
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.997
_exptl_crystal_F_000             2056
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    3.774
_shelx_estimated_absorpt_T_min   0.660
_shelx_estimated_absorpt_T_max   0.752
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.660
_exptl_absorpt_correction_T_max  0.752
_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            25318
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_av_R_equivalents  0.0340
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.151
_diffrn_reflns_theta_max         27.137
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3948
_reflns_number_gt                3797
_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)+(0.0514P)²+24.2387P] 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         3948
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0316
_refine_ls_R_factor_gt           0.0296
_refine_ls_wR_factor_ref         0.1005
_refine_ls_wR_factor_gt          0.0924
_refine_ls_goodness_of_fit_ref   1.207
_refine_ls_restrained_S_all      1.207
_refine_ls_shift/su_max          0.002
_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
Gd1 Gd 0.73366(2) 0.28984(2) 0.17160(2) 0.01944(10) Uani 1 1 d . . . . .
O4 O 0.68021(19) 0.5017(3) 0.63034(19) 0.0274(7) Uani 1 1 d . . . . .
O5 O 0.60673(19) 0.2646(3) 0.1126(2) 0.0326(7) Uani 1 1 d . . . . .
O10 O 0.83188(19) 0.1836(3) 0.2734(2) 0.0306(7) Uani 1 1 d . . . . .
O2 O 0.69278(19) 0.1892(3) 0.2792(2) 0.0251(7) Uani 1 1 d . . . . .
O1 O 0.72096(19) 0.3820(3) 0.2935(2) 0.0283(7) Uani 1 1 d . . . . .
O8 O 0.8216(2) 0.2359(4) 0.1090(3) 0.0442(10) Uani 1 1 d . . . . .
N1 N 0.6273(3) 0.1954(4) 0.4793(3) 0.0297(9) Uani 1 1 d . . . . .
O3 O 0.6977(2) 0.6105(3) 0.5350(2) 0.0317(8) Uani 1 1 d . . . . .
C5 C 0.6662(2) 0.4026(4) 0.5045(3) 0.0214(8) Uani 1 1 d . . . . .
C4 C 0.6365(3) 0.2983(4) 0.5224(3) 0.0272(10) Uani 1 1 d . . . . .
H4 H 0.621978 0.299838 0.567053 0.033 Uiso 1 1 calc R U . . .
O11 O 0.8297(2) 0.4398(3) 0.2155(3) 0.0416(9) Uani 1 1 d . . . . .
C6 C 0.6852(2) 0.4013(4) 0.4357(3) 0.0240(9) Uani 1 1 d . . . . .
H6 H 0.703304 0.470895 0.420267 0.029 Uiso 1 1 calc R U . . .
C1 C 0.6982(2) 0.2881(4) 0.3170(3) 0.0199(8) Uani 1 1 d . . . . .
C2 C 0.6767(2) 0.2954(4) 0.3906(3) 0.0205(8) Uani 1 1 d . . . . .
C9 C 0.5291(3) 0.2842(4) 0.2014(4) 0.0317(11) Uani 1 1 d . . . . .
O300 O 0.5205(3) 0.3918(6) 0.9742(3) 0.0693(15) Uani 1 1 d . . . . .
C7 C 0.6811(2) 0.5115(4) 0.5588(3) 0.0220(8) Uani 1 1 d . . . . .
C3 C 0.6480(3) 0.1952(4) 0.4149(3) 0.0261(9) Uani 1 1 d . . . . .
H3 H 0.642718 0.123680 0.384835 0.031 Uiso 1 1 calc R U . . .
O7 O 0.4763(2) 0.6632(4) 0.2982(3) 0.0436(9) Uani 1 1 d . . . . .
C10 C 0.500000 0.2258(7) 0.250000 0.0350(16) Uani 1 2 d S T P . .
H10 H 0.499999 0.141223 0.250001 0.042 Uiso 1 2 calc R U P . .
N2 N 0.500000 0.4735(7) 0.250000 0.0498(18) Uani 1 2 d S T P . .
C11 C 0.5296(3) 0.4084(5) 0.2017(4) 0.0393(12) Uani 1 1 d . . . . .
H11 H 0.549863 0.450102 0.169374 0.047 Uiso 1 1 calc R U . . .
O100 O 0.9415(4) 0.3790(7) 0.1484(5) 0.103(2) Uani 1 1 d . . . . .
C12 C 0.500000 0.6096(7) 0.250000 0.0336(15) Uani 1 2 d S T P . .
O200 O 0.5679(7) 0.0197(8) -0.0016(8) 0.157(4) Uani 1 1 d . . . . .
O6 O 0.5445(6) 0.0995(8) 0.1293(7) 0.146(4) Uani 1 1 d . . . . .
C8 C 0.5627(6) 0.2123(9) 0.1429(7) 0.084(3) Uani 1 1 d . . . . .
O9 O 0.7091(2) 0.0849(3) 0.1252(2) 0.0374(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Gd1 O5 2.382(4) . ?
Gd1 O9 2.384(4) . ?
Gd1 O10 2.411(3) . ?
Gd1 O11 2.433(4) . ?
Gd1 O1 2.460(3) . ?
Gd1 O8 2.469(4) . ?
Gd1 O3 2.482(3) 6_565 ?
Gd1 O4 2.520(3) 6_565 ?
Gd1 O2 2.567(3) . ?
Gd1 C7 2.870(4) 6_565 ?
Gd1 C1 2.886(4) . ?
O4 C7 1.263(5) . ?
O5 C8 1.318(13) . ?
O2 C1 1.257(5) . ?
O1 C1 1.259(5) . ?
N1 C4 1.334(6) . ?
N1 C3 1.337(6) . ?
O3 C7 1.254(5) . ?
C5 C4 1.382(6) . ?
C5 C6 1.390(6) . ?
C5 C7 1.489(6) . ?
C4 H4 0.9300 . ?
C6 C2 1.382(6) . ?
C6 H6 0.9300 . ?
C1 C2 1.504(6) . ?
C2 C3 1.383(6) . ?
C9 C10 1.359(7) . ?
C9 C11 1.366(7) . ?
C9 C8 1.626(13) . ?
C3 H3 0.9300 . ?
O7 C12 1.258(5) . ?
C10 H10 0.9300 . ?
N2 C11 1.398(7) . ?
N2 C11 1.398(7) 2_655 ?
N2 C12 1.496(10) . ?
C11 H11 0.9300 . ?
O6 C8 1.290(12) . ?

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
O5 Gd1 O9 71.91(13) . . ?
O5 Gd1 O10 135.42(12) . . ?
O9 Gd1 O10 78.61(13) . . ?
O5 Gd1 O11 144.03(13) . . ?
O9 Gd1 O11 141.96(13) . . ?
O10 Gd1 O11 76.19(13) . . ?
O5 Gd1 O1 89.19(13) . . ?
O9 Gd1 O1 127.62(13) . . ?
O10 Gd1 O1 83.00(12) . . ?
O11 Gd1 O1 76.77(13) . . ?
O5 Gd1 O8 127.16(14) . . ?
O9 Gd1 O8 73.32(15) . . ?
O10 Gd1 O8 71.91(13) . . ?
O11 Gd1 O8 72.02(15) . . ?
O1 Gd1 O8 143.62(14) . . ?
O5 Gd1 O3 75.68(13) . 6_565 ?
O9 Gd1 O3 98.04(12) . 6_565 ?
O10 Gd1 O3 142.31(12) . 6_565 ?
O11 Gd1 O3 85.29(14) . 6_565 ?
O1 Gd1 O3 124.55(11) . 6_565 ?
O8 Gd1 O3 71.23(13) . 6_565 ?
O5 Gd1 O4 73.11(12) . 6_565 ?
O9 Gd1 O4 138.59(12) . 6_565 ?
O10 Gd1 O4 142.80(12) . 6_565 ?
O11 Gd1 O4 71.13(12) . 6_565 ?
O1 Gd1 O4 72.76(11) . 6_565 ?
O8 Gd1 O4 112.90(13) . 6_565 ?
O3 Gd1 O4 51.79(10) 6_565 6_565 ?
O5 Gd1 O2 71.73(12) . . ?
O9 Gd1 O2 76.14(12) . . ?
O10 Gd1 O2 69.20(11) . . ?
O11 Gd1 O2 119.42(13) . . ?
O1 Gd1 O2 51.48(11) . . ?
O8 Gd1 O2 134.21(13) . . ?
O3 Gd1 O2 147.10(12) 6_565 . ?
O4 Gd1 O2 112.63(10) 6_565 . ?
O5 Gd1 C7 74.34(13) . 6_565 ?
O9 Gd1 C7 120.56(13) . 6_565 ?
O10 Gd1 C7 150.21(12) . 6_565 ?
O11 Gd1 C7 75.34(13) . 6_565 ?
O1 Gd1 C7 98.80(12) . 6_565 ?
O8 Gd1 C7 91.03(14) . 6_565 ?
O3 Gd1 C7 25.82(11) 6_565 6_565 ?
O4 Gd1 C7 26.08(11) 6_565 6_565 ?
O2 Gd1 C7 134.19(11) . 6_565 ?
O5 Gd1 C1 78.92(13) . . ?
O9 Gd1 C1 101.93(13) . . ?
O10 Gd1 C1 75.30(12) . . ?
O11 Gd1 C1 98.68(13) . . ?
O1 Gd1 C1 25.69(11) . . ?
O8 Gd1 C1 147.16(13) . . ?
O3 Gd1 C1 140.73(11) 6_565 . ?
O4 Gd1 C1 92.35(11) 6_565 . ?
O2 Gd1 C1 25.81(11) . . ?
C7 Gd1 C1 117.64(12) 6_565 . ?
C7 O4 Gd1 92.6(3) . 6_566 ?
C8 O5 Gd1 130.1(5) . . ?
C1 O2 Gd1 91.4(3) . . ?
C1 O1 Gd1 96.4(3) . . ?
C4 N1 C3 117.3(4) . . ?
C7 O3 Gd1 94.7(3) . 6_566 ?
C4 C5 C6 117.9(4) . . ?
C4 C5 C7 121.6(4) . . ?
C6 C5 C7 120.5(4) . . ?
N1 C4 C5 123.8(4) . . ?
N1 C4 H4 118.1 . . ?
C5 C4 H4 118.1 . . ?
C2 C6 C5 119.3(4) . . ?
C2 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
O2 C1 O1 120.6(4) . . ?
O2 C1 C2 120.1(4) . . ?
O1 C1 C2 119.3(4) . . ?
O2 C1 Gd1 62.8(2) . . ?
O1 C1 Gd1 57.9(2) . . ?
C2 C1 Gd1 175.9(3) . . ?
C6 C2 C3 118.2(4) . . ?
C6 C2 C1 121.5(4) . . ?
C3 C2 C1 120.4(4) . . ?
C10 C9 C11 118.4(6) . . ?
C10 C9 C8 122.6(6) . . ?
C11 C9 C8 119.0(6) . . ?
O3 C7 O4 120.4(4) . . ?
O3 C7 C5 120.0(4) . . ?
O4 C7 C5 119.5(4) . . ?
O3 C7 Gd1 59.5(2) . 6_566 ?
O4 C7 Gd1 61.3(2) . 6_566 ?
C5 C7 Gd1 170.7(3) . 6_566 ?
N1 C3 C2 123.6(4) . . ?
N1 C3 H3 118.2 . . ?
C2 C3 H3 118.2 . . ?
C9 C10 C9 123.5(7) 2_655 . ?
C9 C10 H10 118.2 2_655 . ?
C9 C10 H10 118.2 . . ?
C11 N2 C11 118.4(7) . 2_655 ?
C11 N2 C12 120.8(4) . . ?
C11 N2 C12 120.8(4) 2_655 . ?
C9 C11 N2 120.7(6) . . ?
C9 C11 H11 119.7 . . ?
N2 C11 H11 119.7 . . ?
O7 C12 O7 124.1(7) 2_655 . ?
O7 C12 N2 117.9(4) 2_655 . ?
O7 C12 N2 117.9(4) . . ?
O6 C8 O5 122.1(11) . . ?
O6 C8 C9 115.4(11) . . ?
O5 C8 C9 122.5(7) . . ?

_refine_diff_density_max         2.324
_refine_diff_density_min         -1.105
_refine_diff_density_rms         0.300



