# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_Eu_dfdmt
_database_code_depnum_ccdc_archive 'CCDC 1941723'
loop_
_audit_author_name
_audit_author_address
'Wei-Ming Liao'
;Guangdong University of Technology
China
;
_audit_update_record             
;
2019-07-19 deposited with the CCDC.	2020-02-17 downloaded from the CCDC.
;
_audit_creation_date             2019-07-09
_audit_creation_method           
;
Olex2 1.3-alpha
(compiled 2019.05.30 svn.r3610 for OlexSys, GUI svn.r5794)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'C16 Eu F4 O8 S4, H16 N4, 0.25(C8 H32 N4), H2 O'
_chemical_formula_sum            'C18 H26 Eu F4 N5 O9 S4'
_chemical_formula_weight         812.64
_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'
F F 0.0171 0.0103 '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      tetragonal
_space_group_IT_number           85
_space_group_name_H-M_alt        'P 4/n'
_space_group_name_Hall           '-P 4a'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-y+1/2, x, z'
'y, -x+1/2, z'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'y-1/2, -x, -z'
'-y, x-1/2, -z'

_cell_length_a                   12.7820(3)
_cell_length_b                   12.782
_cell_length_c                   8.4363(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1378.32(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9995
_cell_measurement_temperature    230.0
_cell_measurement_theta_max      41.96
_cell_measurement_theta_min      2.89
_shelx_estimated_absorpt_T_max   0.857
_shelx_estimated_absorpt_T_min   0.675
_exptl_absorpt_coefficient_mu    2.662
_exptl_absorpt_correction_T_max  0.852
_exptl_absorpt_correction_T_min  0.760
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.958
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.086
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            26569
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.311
_diffrn_reflns_theta_min         3.188
_diffrn_ambient_temperature      230.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.996
_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                3028
_reflns_number_total             3342
_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       ?
_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    ?
_refine_diff_density_max         1.456
_refine_diff_density_min         -1.375
_refine_diff_density_rms         0.102
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     136
_refine_ls_number_reflns         3342
_refine_ls_number_restraints     42
_refine_ls_R_factor_all          0.0279
_refine_ls_R_factor_gt           0.0214
_refine_ls_restrained_S_all      1.054
_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)+(0.0197P)²+1.0864P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0466
_refine_ls_wR_factor_ref         0.0510
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O3-H3
 0.84 with sigma of 0.02
 H3-H3_$1
 1.36 with sigma of 0.02
 N1-C6 \\sim N1-C5
 with sigma of 0.02
 N2-H2A \\sim N2-H2B \\sim N2-H2C \\sim N2-H2D
 with sigma of 0.02
 H2A-H2B \\sim H2A-H2C \\sim H2A-H2D \\sim H2B-H2C \\sim H2B-H2D \\sim H2C-H2D
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
N1 \\sim C6 \\sim C5: within 2.6A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2.6A
4. Others
 Fixed Sof: N1(0.25) H1A(0.25) H1B(0.25) C6(0.25) H6A(0.25) H6B(0.25)
 H6C(0.25) C5(0.25) H5A(0.25) H5B(0.25) H5C(0.25) H3(0.5)
5.a Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B)
5.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C5(H5A,H5B,H5C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.2500 0.2500 0.15842(2) 0.01020(3) Uani 1 4 d S T P . .
S1 S 0.25707(3) 0.44694(3) -0.03212(4) 0.01611(7) Uani 1 1 d . . . . .
F1 F 0.41052(7) 0.49527(8) -0.29033(11) 0.02060(18) Uani 1 1 d . . . . .
O1 O 0.34322(8) 0.37586(8) 0.31179(12) 0.01428(17) Uani 1 1 d . . . . .
O2 O 0.36652(10) 0.54259(9) 0.37665(13) 0.0210(2) Uani 1 1 d . . . . .
C1 C 0.37830(10) 0.46668(10) 0.28523(15) 0.0120(2) Uani 1 1 d . . . . .
C2 C 0.43942(10) 0.48366(10) 0.13480(14) 0.0115(2) Uani 1 1 d . . . . .
C3 C 0.39018(10) 0.47794(10) -0.01302(15) 0.0119(2) Uani 1 1 d . . . . .
C4 C 0.45431(10) 0.49639(10) -0.14310(15) 0.0126(2) Uani 1 1 d . . . . .
N2 N 0.48098(12) 0.29890(10) 0.57448(16) 0.0203(2) Uani 1 1 d D . . . .
H2A H 0.5276(15) 0.3465(15) 0.586(3) 0.038(7) Uiso 1 1 d D . . . .
H2B H 0.4624(15) 0.2781(16) 0.6669(18) 0.024(6) Uiso 1 1 d D . . . .
H2C H 0.5080(16) 0.2471(13) 0.523(2) 0.033(7) Uiso 1 1 d D . . . .
H2D H 0.4284(14) 0.3222(17) 0.524(2) 0.042(7) Uiso 1 1 d D . . . .
N1 N 0.2903(5) 0.7070(6) 0.0123(11) 0.0389(16) Uani 0.25 1 d D U P A -1
H1A H 0.2647 0.6416 0.0194 0.047 Uiso 0.25 1 calc R U P A -1
H1B H 0.3606 0.7032 0.0110 0.047 Uiso 0.25 1 calc R U P A -1
C6 C 0.255(4) 0.770(3) 0.151(3) 0.051(5) Uani 0.25 1 d D U P A -1
H6A H 0.1796 0.7663 0.1600 0.077 Uiso 0.25 1 calc R U P A -1
H6B H 0.2762 0.8424 0.1370 0.077 Uiso 0.25 1 calc R U P A -1
H6C H 0.2868 0.7425 0.2471 0.077 Uiso 0.25 1 calc R U P A -1
C5 C 0.252(6) 0.758(4) -0.137(3) 0.048(6) Uani 0.25 1 d D U P A -1
H5A H 0.2915 0.7313 -0.2264 0.073 Uiso 0.25 1 calc R U P A -1
H5B H 0.2612 0.8329 -0.1291 0.073 Uiso 0.25 1 calc R U P A -1
H5C H 0.1784 0.7419 -0.1514 0.073 Uiso 0.25 1 calc R U P A -1
O3 O 0.2500 0.2500 -0.3181(4) 0.0370(7) Uani 1 4 d DS T P . .
H3 H 0.198(2) 0.265(8) -0.259(4) 0.055 Uiso 0.5 1 d D U P B -1


_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 S1 2.9881(4) 2 ?
Eu1 S1 2.9881(4) 3 ?
Eu1 S1 2.9881(4) 4 ?
Eu1 S1 2.9881(4) . ?
Eu1 O1 2.3837(10) 4 ?
Eu1 O1 2.3837(10) . ?
Eu1 O1 2.3837(10) 2 ?
Eu1 O1 2.3837(10) 3 ?
S1 C3 1.7543(13) . ?
F1 C4 1.3624(15) . ?
O1 C1 1.2644(16) . ?
O2 C1 1.2486(16) . ?
C1 C2 1.5060(17) . ?
C2 C3 1.3988(18) . ?
C2 C4 1.3839(18) 5_665 ?
C3 C4 1.3899(18) . ?
C4 C2 1.3839(18) 5_665 ?
N2 H2A 0.856(15) . ?
N2 H2B 0.857(14) . ?
N2 H2C 0.863(15) . ?
N2 H2D 0.851(15) . ?
N1 H1A 0.9000 . ?
N1 H1B 0.9000 . ?
N1 C6 1.49(2) . ?
N1 C5 1.50(3) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 H6C 0.9700 . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C5 H5C 0.9700 . ?
O3 H3 0.851(17) . ?

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
S1 Eu1 S1 73.179(7) 2 3 ?
S1 Eu1 S1 73.179(7) 3 . ?
S1 Eu1 S1 73.180(7) 4 . ?
S1 Eu1 S1 114.913(15) 4 3 ?
S1 Eu1 S1 114.913(15) 2 . ?
S1 Eu1 S1 73.179(7) 2 4 ?
O1 Eu1 S1 83.76(3) 4 2 ?
O1 Eu1 S1 151.13(3) 4 3 ?
O1 Eu1 S1 151.13(3) 2 . ?
O1 Eu1 S1 73.04(2) 2 2 ?
O1 Eu1 S1 133.84(3) . 3 ?
O1 Eu1 S1 133.84(3) 3 2 ?
O1 Eu1 S1 73.04(2) . . ?
O1 Eu1 S1 151.13(3) . 2 ?
O1 Eu1 S1 83.76(3) 2 3 ?
O1 Eu1 S1 73.04(2) 4 4 ?
O1 Eu1 S1 133.84(3) 4 . ?
O1 Eu1 S1 133.84(3) 2 4 ?
O1 Eu1 S1 83.76(3) 3 . ?
O1 Eu1 S1 151.13(3) 3 4 ?
O1 Eu1 S1 83.76(3) . 4 ?
O1 Eu1 S1 73.04(2) 3 3 ?
O1 Eu1 O1 72.86(2) 4 2 ?
O1 Eu1 O1 114.25(5) 2 . ?
O1 Eu1 O1 72.86(2) 4 . ?
O1 Eu1 O1 114.25(5) 4 3 ?
O1 Eu1 O1 72.86(2) 3 . ?
O1 Eu1 O1 72.86(2) 2 3 ?
C3 S1 Eu1 99.80(4) . . ?
C1 O1 Eu1 134.48(9) . . ?
O1 C1 C2 117.75(11) . . ?
O2 C1 O1 124.14(12) . . ?
O2 C1 C2 118.10(12) . . ?
C3 C2 C1 120.68(11) . . ?
C4 C2 C1 119.55(11) 5_665 . ?
C4 C2 C3 119.76(11) 5_665 . ?
C2 C3 S1 122.01(10) . . ?
C4 C3 S1 122.53(10) . . ?
C4 C3 C2 115.45(11) . . ?
F1 C4 C2 116.83(11) . 5_665 ?
F1 C4 C3 118.41(11) . . ?
C2 C4 C3 124.76(12) 5_665 . ?
H2A N2 H2B 108.1(14) . . ?
H2A N2 H2C 108.8(14) . . ?
H2A N2 H2D 110.9(15) . . ?
H2B N2 H2C 109.2(15) . . ?
H2B N2 H2D 110.3(15) . . ?
H2C N2 H2D 109.4(15) . . ?
H1A N1 H1B 108.3 . . ?
C6 N1 H1A 109.9 . . ?
C6 N1 H1B 109.9 . . ?
C6 N1 C5 109(3) . . ?
C5 N1 H1A 109.9 . . ?
C5 N1 H1B 109.9 . . ?
N1 C6 H6A 109.5 . . ?
N1 C6 H6B 109.5 . . ?
N1 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N1 C5 H5A 109.5 . . ?
N1 C5 H5B 109.5 . . ?
N1 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O2 0.856(15) 1.986(15) 2.8416(18) 177(2) 5_666
N2 H2B S1 0.857(14) 2.586(14) 3.4228(14) 165.5(18) 4_556
N2 H2B F1 0.857(14) 2.47(2) 2.9154(16) 112.8(16) 4_556
N2 H2C O2 0.863(15) 1.957(15) 2.8065(17) 168(2) 4
N2 H2D O1 0.851(15) 2.203(16) 2.9966(17) 155(2) .
N1 H1A S1 0.90 2.53 3.372(7) 156.5 .
N1 H1B S1 0.90 2.56 3.423(7) 160.7 8_665
C5 H5B S1 0.97 2.94 3.88(5) 163.1 2_565
O3 H3 S1 0.851(17) 2.67(3) 3.488(2) 163(8) 3

_olex2_submission_special_instructions 'No special instructions were received'
_exptl_crystal_recrystallization_method 'solvothermal method'
_chemical_properties_physical    Moisture-sensitive
_exptl_crystal_preparation       'Magnetic properties'
