# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2023

####################################################################### 
# 
# 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_1_sq
_database_code_depnum_ccdc_archive 'CCDC 2219553'
loop_
_audit_author_name
_audit_author_address
WRN
;Changchun University of Science and Technology
China
;
_audit_update_record             
;
2022-11-14 deposited with the CCDC.	2023-01-17 downloaded from the CCDC.
;
_audit_creation_date             2022-09-14
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H13 Eu N1.5 O7 S'
_chemical_formula_sum            'C14 H13 Eu N1.50 O7 S'
_chemical_formula_weight         498.28
_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'
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'
S S 0.1246 0.1234 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.967(6)
_cell_length_b                   10.323(7)
_cell_length_c                   10.471(7)
_cell_angle_alpha                115.226(8)
_cell_angle_beta                 91.750(8)
_cell_angle_gamma                109.208(8)
_cell_volume                     811.4(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1926
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.04
_cell_measurement_theta_min      2.36
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    4.032
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.040
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             485
_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  0.0242
_diffrn_reflns_av_unetI/netI     0.0572
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.957
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4664
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.627
_diffrn_reflns_theta_min         2.194
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3099
_reflns_number_total             3628
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         2.160
_refine_diff_density_min         -1.031
_refine_diff_density_rms         0.188
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         3628
_refine_ls_number_restraints     22
_refine_ls_R_factor_all          0.0570
_refine_ls_R_factor_gt           0.0450
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0567P)²+2.6874P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1095
_refine_ls_wR_factor_ref         0.1162
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C8-C13
 1.395 with sigma of 0.001
 C8-C14
 1.395 with sigma of 0.001
3. Rigid bond restraints
 N1, C10
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 C13, C14
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
 C13, N2
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(N2) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(C13) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C13) \\sim Ueq, Uanis(C14) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
5. Others
 Fixed Sof: N2(0.5) H2A(0.5) H2B(0.5)
6.a Rotating group:
 N2(H2A,H2B)
6.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C14(H14)
6.c Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_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
Eu1 Eu 0.30649(4) 0.05997(4) 0.53897(4) 0.02619(13) Uani 1 1 d . . . . .
S1 S 0.2599(2) 0.4355(2) 0.4285(2) 0.0387(4) Uani 1 1 d . . . . .
O1 O 0.4522(6) 0.7295(6) 0.4223(6) 0.0425(13) Uani 1 1 d . . . . .
O2 O 0.2396(6) 0.7900(5) 0.3941(6) 0.0359(12) Uani 1 1 d . . . . .
O3 O -0.1053(7) 0.0662(6) 0.3675(6) 0.0445(14) Uani 1 1 d . . . . .
O4 O 0.4831(7) 0.0104(6) 0.6600(6) 0.0449(14) Uani 1 1 d . . . . .
O5 O 0.6988(8) -0.0299(8) 0.7005(6) 0.0509(15) Uani 1 1 d . . . . .
O6 O 0.3262(7) 0.2575(7) 0.7717(6) 0.0494(15) Uani 1 1 d . . . . .
O7 O 0.1429(8) 0.1751(8) 0.5016(7) 0.0543(16) Uani 1 1 d . . . . .
C1 C 0.3043(9) 0.7011(8) 0.3967(7) 0.0303(15) Uani 1 1 d . . . . .
C2 C 0.5748(10) -0.0082(8) 0.7386(7) 0.0370(18) Uani 1 1 d . . . . .
C3 C 0.0704(9) 0.2963(8) 0.3791(7) 0.0301(15) Uani 1 1 d . . . . .
C4 C 0.1955(9) 0.5465(8) 0.3751(7) 0.0290(14) Uani 1 1 d . . . . .
C5 C 0.0335(9) 0.4747(8) 0.3199(8) 0.0359(16) Uani 1 1 d . . . . .
H5 H -0.024439 0.516357 0.284370 0.043 Uiso 1 1 calc R . . . .
C6 C 0.0316(9) 0.1682(8) 0.4169(8) 0.0333(16) Uani 1 1 d . . . . .
C7 C -0.0371(9) 0.3339(8) 0.3217(8) 0.0348(16) Uani 1 1 d . . . . .
H7 H -0.146142 0.271986 0.287307 0.042 Uiso 1 1 calc R . . . .
N1 N 0.3052(12) 0.4840(11) 0.9001(10) 0.073(3) Uani 1 1 d . U . . .
C8 C 0.5388(8) -0.0047(9) 0.8749(7) 0.049(2) Uani 1 1 d D . . . .
C9 C 0.2511(16) 0.5888(12) 1.0137(12) 0.078(4) Uani 1 1 d . . . . .
H9A H 0.324355 0.633750 1.103539 0.117 Uiso 1 1 calc GR . . . .
H9B H 0.145315 0.532710 1.020982 0.117 Uiso 1 1 calc GR . . . .
H9C H 0.247853 0.669173 0.991674 0.117 Uiso 1 1 calc GR . . . .
C10 C 0.4366(13) 0.5510(12) 0.8358(12) 0.069(3) Uani 1 1 d . U . . .
H10A H 0.405157 0.611050 0.799197 0.103 Uiso 1 1 calc GR . . . .
H10B H 0.455869 0.468992 0.758672 0.103 Uiso 1 1 calc GR . . . .
H10C H 0.533318 0.616223 0.908360 0.103 Uiso 1 1 calc GR . . . .
C11 C 0.1160(15) 0.2673(14) 0.9165(16) 0.092(4) Uani 1 1 d . . . . .
H11A H 0.018157 0.263493 0.872507 0.138 Uiso 1 1 calc GR . . . .
H11B H 0.134945 0.329236 1.019012 0.138 Uiso 1 1 calc GR . . . .
H11C H 0.106574 0.164420 0.895002 0.138 Uiso 1 1 calc GR . . . .
C12 C 0.2604(16) 0.3404(13) 0.8563(12) 0.074(3) Uani 1 1 d . . . . .
C13 C 0.6306(14) -0.0111(11) 0.9805(11) 0.063(3) Uani 1 1 d D U . . .
C14 C 0.3998(11) 0.0122(12) 0.9230(15) 0.079(3) Uani 1 1 d D U . . .
H14 H 0.329269 0.025123 0.866697 0.095 Uiso 1 1 calc R . . . .
N2 N 0.773(4) -0.024(4) 0.948(3) 0.113(8) Uani 0.5 1 d . U P . .
H2A H 0.755105 -0.105588 0.866083 0.136 Uiso 0.5 1 d GR . P . .
H2B H 0.832838 0.056823 0.941155 0.136 Uiso 0.5 1 d GR . P . .


_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 Eu1 4.047(2) 2_656 ?
Eu1 O1 2.381(5) 2_666 ?
Eu1 O2 2.381(5) 1_545 ?
Eu1 O3 2.358(5) 2_556 ?
Eu1 O4 2.311(5) . ?
Eu1 O4 2.877(6) 2_656 ?
Eu1 O5 2.389(6) 2_656 ?
Eu1 O6 2.372(6) . ?
Eu1 O7 2.286(6) . ?
Eu1 C2 3.018(8) 2_656 ?
S1 C3 1.710(7) . ?
S1 C4 1.710(7) . ?
O1 C1 1.254(9) . ?
O2 C1 1.246(9) . ?
O3 C6 1.237(9) . ?
O4 C2 1.261(9) . ?
O5 C2 1.249(10) . ?
O6 C12 1.259(13) . ?
O7 C6 1.278(10) . ?
C1 C4 1.485(9) . ?
C2 C8 1.461(10) . ?
C3 C6 1.476(10) . ?
C3 C7 1.361(11) . ?
C4 C5 1.367(10) . ?
C5 C7 1.390(10) . ?
N1 C9 1.451(12) . ?
N1 C10 1.493(14) . ?
N1 C12 1.259(14) . ?
C8 C13 1.3949(12) . ?
C8 C14 1.3948(13) . ?
C11 C12 1.567(18) . ?
C13 C14 1.059(14) 2_657 ?
C13 N2 1.37(3) . ?

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 Eu1 Eu1 66.35(14) 2_666 2_656 ?
O1 Eu1 O4 64.07(17) 2_666 2_656 ?
O1 Eu1 O5 79.8(2) 2_666 2_656 ?
O1 Eu1 C2 69.25(19) 2_666 2_656 ?
O2 Eu1 Eu1 66.00(13) 1_545 2_656 ?
O2 Eu1 O1 128.94(19) 1_545 2_666 ?
O2 Eu1 O4 66.38(17) 1_545 2_656 ?
O2 Eu1 O5 76.1(2) 1_545 2_656 ?
O2 Eu1 C2 71.08(19) 1_545 2_656 ?
O3 Eu1 Eu1 120.06(15) 2_556 2_656 ?
O3 Eu1 O1 149.6(2) 2_556 2_666 ?
O3 Eu1 O2 73.75(19) 2_556 1_545 ?
O3 Eu1 O4 139.31(18) 2_556 2_656 ?
O3 Eu1 O5 129.3(2) 2_556 2_656 ?
O3 Eu1 O6 76.3(2) 2_556 . ?
O3 Eu1 C2 140.8(2) 2_556 2_656 ?
O4 Eu1 Eu1 44.06(16) . 2_656 ?
O4 Eu1 Eu1 33.95(11) 2_656 2_656 ?
O4 Eu1 O1 80.9(2) . 2_666 ?
O4 Eu1 O2 77.68(19) . 1_545 ?
O4 Eu1 O3 86.2(2) . 2_556 ?
O4 Eu1 O4 78.0(2) . 2_656 ?
O4 Eu1 O5 125.4(2) . 2_656 ?
O4 Eu1 O6 83.7(2) . . ?
O4 Eu1 C2 24.54(18) 2_656 2_656 ?
O4 Eu1 C2 102.5(2) . 2_656 ?
O5 Eu1 Eu1 81.46(15) 2_656 2_656 ?
O5 Eu1 O4 47.64(18) 2_656 2_656 ?
O5 Eu1 C2 23.2(2) 2_656 2_656 ?
O6 Eu1 Eu1 117.36(16) . 2_656 ?
O6 Eu1 O1 75.1(2) . 2_666 ?
O6 Eu1 O2 145.5(2) . 1_545 ?
O6 Eu1 O4 137.24(18) . 2_656 ?
O6 Eu1 O5 137.6(2) . 2_656 ?
O6 Eu1 C2 142.1(2) . 2_656 ?
O7 Eu1 Eu1 149.66(17) . 2_656 ?
O7 Eu1 O1 93.6(2) . 2_666 ?
O7 Eu1 O2 120.0(2) . 1_545 ?
O7 Eu1 O3 88.9(2) . 2_556 ?
O7 Eu1 O4 117.5(2) . 2_656 ?
O7 Eu1 O4 159.4(2) . . ?
O7 Eu1 O5 72.3(2) . 2_656 ?
O7 Eu1 O6 75.7(2) . . ?
O7 Eu1 C2 93.9(2) . 2_656 ?
C2 Eu1 Eu1 58.48(15) 2_656 2_656 ?
C4 S1 C3 92.7(4) . . ?
C1 O1 Eu1 135.4(5) . 2_666 ?
C1 O2 Eu1 132.0(4) . 1_565 ?
C6 O3 Eu1 135.8(5) . 2_556 ?
Eu1 O4 Eu1 102.0(2) . 2_656 ?
C2 O4 Eu1 84.0(5) . 2_656 ?
C2 O4 Eu1 173.6(6) . . ?
C2 O5 Eu1 108.0(5) . 2_656 ?
C12 O6 Eu1 147.8(7) . . ?
C6 O7 Eu1 147.7(6) . . ?
O1 C1 C4 115.6(7) . . ?
O2 C1 O1 127.4(7) . . ?
O2 C1 C4 116.9(6) . . ?
O4 C2 Eu1 71.5(4) . 2_656 ?
O4 C2 C8 121.0(8) . . ?
O5 C2 Eu1 48.9(4) . 2_656 ?
O5 C2 O4 120.0(7) . . ?
O5 C2 C8 119.0(7) . . ?
C8 C2 Eu1 166.5(6) . 2_656 ?
C6 C3 S1 122.3(6) . . ?
C7 C3 S1 110.7(5) . . ?
C7 C3 C6 126.3(7) . . ?
C1 C4 S1 122.5(5) . . ?
C5 C4 S1 109.7(5) . . ?
C5 C4 C1 127.7(7) . . ?
C4 C5 C7 114.1(7) . . ?
O3 C6 O7 125.6(7) . . ?
O3 C6 C3 118.0(7) . . ?
O7 C6 C3 116.4(7) . . ?
C3 C7 C5 112.8(7) . . ?
C9 N1 C10 118.2(9) . . ?
C12 N1 C9 126.1(12) . . ?
C12 N1 C10 115.4(10) . . ?
C13 C8 C2 129.3(9) . . ?
C14 C8 C2 122.9(9) . . ?
C14 C8 C13 107.8(9) . . ?
O6 C12 C11 120.3(10) . . ?
N1 C12 O6 123.8(13) . . ?
N1 C12 C11 115.8(11) . . ?
C14 C13 C8 128.0(14) 2_657 . ?
C14 C13 N2 118.3(12) 2_657 . ?
N2 C13 C8 113.6(13) . . ?
C13 C14 C8 124.1(15) 2_657 . ?

_olex2_submission_special_instructions 'No special instructions were received'
