# 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_12_sq
_audit_block_doi                 10.5517/ccdc.csd.cc2d4frr
_database_code_depnum_ccdc_archive 'CCDC 2208804'
loop_
_audit_author_name
_audit_author_address
'Zhi-Qing Liu'
;Guangdong University of Technology
China
;
_audit_update_record             
;
2022-09-22 deposited with the CCDC.	2022-11-29 downloaded from the CCDC.
;
_audit_creation_date             2022-09-22
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.08.20 svn.r13c46975 for OlexSys, GUI svn.r6396)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H14 Eu2 F4 N2 O10 S4'
_chemical_formula_sum            'C22 H14 Eu2 F4 N2 O10 S4'
_chemical_formula_weight         974.51
_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      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                   9.4105(14)
_cell_length_b                   9.5147(14)
_cell_length_c                   9.8831(15)
_cell_angle_alpha                106.078(2)
_cell_angle_beta                 94.529(2)
_cell_angle_gamma                92.030(2)
_cell_volume                     846.1(2)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    5091
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      27.76
_cell_measurement_theta_min      2.63
_shelx_estimated_absorpt_T_max   0.424
_shelx_estimated_absorpt_T_min   0.381
_exptl_absorpt_coefficient_mu    3.990
_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            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.912
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             466
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.26
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.905
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            6768
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.905
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.771
_diffrn_reflns_theta_min         2.916
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.905
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3422
_reflns_number_total             3619
_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 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         1.492
_refine_diff_density_min         -1.192
_refine_diff_density_rms         0.139
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     201
_refine_ls_number_reflns         3619
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0254
_refine_ls_restrained_S_all      1.042
_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)+(0.0300P)²+0.4937P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0650
_refine_ls_wR_factor_ref         0.0658
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_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 0.72177(2) 0.55348(2) 0.47797(2) 0.01248(7) Uani 1 1 d . . . . .
S1 S 0.81589(10) 0.71986(10) 0.29680(10) 0.0255(2) Uani 1 1 d . . . . .
S2 S 0.31128(9) 0.65092(9) -0.19948(9) 0.01794(18) Uani 1 1 d . . . . .
F1 F 0.2512(2) 0.6176(2) 0.0797(2) 0.0254(5) Uani 1 1 d . . . . .
F2 F 0.8026(3) 1.0347(3) 0.2988(3) 0.0386(6) Uani 1 1 d . . . . .
O1 O 1.1717(2) 0.6656(3) 0.5140(3) 0.0219(5) Uani 1 1 d . . . . .
O2 O 0.9513(2) 0.6478(3) 0.5790(3) 0.0201(5) Uani 1 1 d . . . . .
O3 O 0.4720(2) 0.5463(3) 0.3844(3) 0.0195(5) Uani 1 1 d . . . . .
O4 O 0.2734(3) 0.4378(3) 0.2649(3) 0.0266(6) Uani 1 1 d . . . . .
O5 O 0.6482(3) 0.7873(3) 0.5928(3) 0.0364(7) Uani 1 1 d . . . . .
N00B N 0.5759(4) 1.0046(4) 0.7196(4) 0.0333(8) Uani 1 1 d . . . . .
C1 C 1.0503(3) 0.7135(3) 0.5372(4) 0.0158(7) Uani 1 1 d . . . . .
C2 C 1.0219(3) 0.8610(4) 0.5156(4) 0.0175(7) Uani 1 1 d . . . . .
C3 C 0.9165(4) 0.8731(4) 0.4109(4) 0.0179(7) Uani 1 1 d . . . . .
C4 C 0.9001(4) 1.0145(4) 0.4004(4) 0.0202(7) Uani 1 1 d . . . . .
C5 C 0.4144(3) 0.5627(4) -0.0945(4) 0.0155(7) Uani 1 1 d . . . . .
C6 C 0.3751(3) 0.5558(4) 0.0364(4) 0.0172(7) Uani 1 1 d . . . . .
C7 C 0.4539(3) 0.4977(4) 0.1302(4) 0.0156(6) Uani 1 1 d . . . . .
C8 C 0.3961(3) 0.4945(4) 0.2671(4) 0.0166(7) Uani 1 1 d . . . . .
C9 C 0.5831(4) 0.8620(4) 0.6868(5) 0.0350(10) Uani 1 1 d . . . . .
H9 H 0.534258 0.812998 0.740054 0.042 Uiso 1 1 calc R U . . .
C10 C 0.6418(9) 1.0919(7) 0.6380(8) 0.081(2) Uani 1 1 d . . . . .
H10A H 0.731777 1.136063 0.686540 0.121 Uiso 1 1 calc R U . . .
H10B H 0.580048 1.167192 0.627817 0.121 Uiso 1 1 calc R U . . .
H10C H 0.657019 1.029858 0.546269 0.121 Uiso 1 1 calc R U . . .
C11 C 0.4998(5) 1.0816(6) 0.8393(6) 0.0505(13) Uani 1 1 d . . . . .
H11A H 0.446808 1.011545 0.872290 0.076 Uiso 1 1 calc R U . . .
H11B H 0.435367 1.145758 0.809916 0.076 Uiso 1 1 calc R U . . .
H11C H 0.567334 1.137944 0.914239 0.076 Uiso 1 1 calc R U . . .


_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 4.3449(7) 2_666 ?
Eu1 S1 2.8667(10) . ?
Eu1 S2 2.8830(9) 2_665 ?
Eu1 O1 2.363(2) 2_766 ?
Eu1 O2 2.344(2) . ?
Eu1 O3 2.657(2) 2_666 ?
Eu1 O3 2.449(2) . ?
Eu1 O4 2.516(3) 2_666 ?
Eu1 O5 2.356(3) . ?
Eu1 C8 2.971(3) 2_666 ?
S1 C3 1.766(3) . ?
S2 C5 1.761(3) . ?
F1 C6 1.370(4) . ?
F2 C4 1.364(4) . ?
O1 C1 1.260(4) . ?
O2 C1 1.261(4) . ?
O3 C8 1.275(4) . ?
O4 C8 1.253(4) . ?
O5 C9 1.224(5) . ?
N00B C9 1.310(5) . ?
N00B C10 1.462(7) . ?
N00B C11 1.463(6) . ?
C1 C2 1.506(4) . ?
C2 C3 1.408(5) . ?
C2 C4 1.389(5) 2_776 ?
C3 C4 1.390(5) . ?
C5 C6 1.391(5) . ?
C5 C7 1.414(5) 2_665 ?
C6 C7 1.385(5) . ?
C7 C8 1.505(5) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?

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 Eu1 124.96(2) . 2_666 ?
S1 Eu1 S2 75.68(3) . 2_665 ?
S1 Eu1 C8 156.37(7) . 2_666 ?
S2 Eu1 Eu1 88.433(18) 2_665 2_666 ?
S2 Eu1 C8 125.33(7) 2_665 2_666 ?
O1 Eu1 Eu1 101.43(6) 2_766 2_666 ?
O1 Eu1 S1 120.88(7) 2_766 . ?
O1 Eu1 S2 70.77(7) 2_766 2_665 ?
O1 Eu1 O3 82.05(8) 2_766 2_666 ?
O1 Eu1 O3 120.12(8) 2_766 . ?
O1 Eu1 O4 77.01(9) 2_766 2_666 ?
O1 Eu1 C8 79.79(9) 2_766 2_666 ?
O2 Eu1 Eu1 150.42(6) . 2_666 ?
O2 Eu1 S1 75.86(6) . . ?
O2 Eu1 S2 119.13(7) . 2_665 ?
O2 Eu1 O1 79.97(8) . 2_766 ?
O2 Eu1 O3 123.83(8) . 2_666 ?
O2 Eu1 O3 159.91(9) . . ?
O2 Eu1 O4 74.16(8) . 2_666 ?
O2 Eu1 O5 85.33(10) . . ?
O2 Eu1 C8 98.79(9) . 2_666 ?
O3 Eu1 Eu1 33.16(6) . 2_666 ?
O3 Eu1 Eu1 30.26(5) 2_666 2_666 ?
O3 Eu1 S1 92.42(6) . . ?
O3 Eu1 S1 153.92(6) 2_666 . ?
O3 Eu1 S2 72.16(6) . 2_665 ?
O3 Eu1 S2 103.74(6) 2_666 2_665 ?
O3 Eu1 O3 63.42(9) . 2_666 ?
O3 Eu1 O4 108.07(8) . 2_666 ?
O3 Eu1 C8 85.38(8) . 2_666 ?
O3 Eu1 C8 25.39(8) 2_666 2_666 ?
O4 Eu1 Eu1 77.38(5) 2_666 2_666 ?
O4 Eu1 S1 141.28(6) 2_666 . ?
O4 Eu1 S2 141.31(7) 2_666 2_665 ?
O4 Eu1 O3 49.98(7) 2_666 2_666 ?
O4 Eu1 C8 24.66(8) 2_666 2_666 ?
O5 Eu1 Eu1 79.45(7) . 2_666 ?
O5 Eu1 S1 79.13(8) . . ?
O5 Eu1 S2 138.33(8) . 2_665 ?
O5 Eu1 O1 150.61(11) . 2_766 ?
O5 Eu1 O3 85.31(10) . 2_666 ?
O5 Eu1 O3 76.35(9) . . ?
O5 Eu1 O4 74.54(11) . 2_666 ?
O5 Eu1 C8 77.48(10) . 2_666 ?
C8 Eu1 Eu1 53.28(6) 2_666 2_666 ?
C3 S1 Eu1 105.02(12) . . ?
C5 S2 Eu1 104.96(11) . 2_665 ?
C1 O1 Eu1 134.0(2) . 2_766 ?
C1 O2 Eu1 132.9(2) . . ?
Eu1 O3 Eu1 116.58(9) . 2_666 ?
C8 O3 Eu1 91.22(19) . 2_666 ?
C8 O3 Eu1 138.2(2) . . ?
C8 O4 Eu1 98.5(2) . 2_666 ?
C9 O5 Eu1 147.6(3) . . ?
C9 N00B C10 121.6(4) . . ?
C9 N00B C11 120.6(4) . . ?
C10 N00B C11 117.8(4) . . ?
O1 C1 O2 124.8(3) . . ?
O1 C1 C2 117.6(3) . . ?
O2 C1 C2 117.6(3) . . ?
C3 C2 C1 120.3(3) . . ?
C4 C2 C1 119.9(3) 2_776 . ?
C4 C2 C3 119.9(3) 2_776 . ?
C2 C3 S1 122.7(3) . . ?
C4 C3 S1 122.1(3) . . ?
C4 C3 C2 115.2(3) . . ?
F2 C4 C2 116.3(3) . 2_776 ?
F2 C4 C3 118.7(3) . . ?
C2 C4 C3 125.0(3) 2_776 . ?
C6 C5 S2 121.5(3) . . ?
C6 C5 C7 114.6(3) . 2_665 ?
C7 C5 S2 123.8(3) 2_665 . ?
F1 C6 C5 117.5(3) . . ?
F1 C6 C7 116.8(3) . . ?
C7 C6 C5 125.6(3) . . ?
C5 C7 C8 120.4(3) 2_665 . ?
C6 C7 C5 119.8(3) . 2_665 ?
C6 C7 C8 119.8(3) . . ?
O3 C8 Eu1 63.39(18) . 2_666 ?
O3 C8 C7 120.5(3) . . ?
O4 C8 Eu1 56.88(18) . 2_666 ?
O4 C8 O3 120.0(3) . . ?
O4 C8 C7 119.5(3) . . ?
C7 C8 Eu1 172.6(2) . 2_666 ?
O5 C9 N00B 126.2(4) . . ?
O5 C9 H9 116.9 . . ?
N00B C9 H9 116.9 . . ?
N00B C10 H10A 109.5 . . ?
N00B C10 H10B 109.5 . . ?
N00B C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N00B C11 H11A 109.5 . . ?
N00B C11 H11B 109.5 . . ?
N00B C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?

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
Eu1 S1 C3 C2 47.4(3) . . . . ?
Eu1 S1 C3 C4 -134.7(3) . . . . ?
Eu1 S2 C5 C6 -131.9(3) 2_665 . . . ?
Eu1 S2 C5 C7 52.3(3) 2_665 . . 2_665 ?
Eu1 O1 C1 O2 2.8(6) 2_766 . . . ?
Eu1 O1 C1 C2 -178.1(2) 2_766 . . . ?
Eu1 O2 C1 O1 -117.3(3) . . . . ?
Eu1 O2 C1 C2 63.6(4) . . . . ?
Eu1 O3 C8 Eu1 134.0(3) . . . 2_666 ?
Eu1 O3 C8 O4 5.8(3) 2_666 . . . ?
Eu1 O3 C8 O4 139.8(3) . . . . ?
Eu1 O3 C8 C7 -172.9(3) 2_666 . . . ?
Eu1 O3 C8 C7 -38.9(5) . . . . ?
Eu1 O4 C8 O3 -6.2(3) 2_666 . . . ?
Eu1 O4 C8 C7 172.5(3) 2_666 . . . ?
Eu1 O5 C9 N00B 175.8(3) . . . . ?
S1 C3 C4 F2 0.2(5) . . . . ?
S1 C3 C4 C2 -178.4(3) . . . 2_776 ?
S2 C5 C6 F1 1.4(4) . . . . ?
S2 C5 C6 C7 -175.5(3) . . . . ?
F1 C6 C7 C5 -177.6(3) . . . 2_665 ?
F1 C6 C7 C8 4.6(5) . . . . ?
O1 C1 C2 C3 116.4(4) . . . . ?
O1 C1 C2 C4 -63.7(5) . . . 2_776 ?
O2 C1 C2 C3 -64.5(5) . . . . ?
O2 C1 C2 C4 115.4(4) . . . 2_776 ?
C1 C2 C3 S1 -1.8(5) . . . . ?
C1 C2 C3 C4 -179.8(3) . . . . ?
C2 C3 C4 F2 178.2(3) . . . . ?
C2 C3 C4 C2 -0.4(6) . . . 2_776 ?
C4 C2 C3 S1 178.3(3) 2_776 . . . ?
C4 C2 C3 C4 0.3(6) 2_776 . . . ?
C5 C6 C7 C5 -0.7(6) . . . 2_665 ?
C5 C6 C7 C8 -178.5(3) . . . . ?
C5 C7 C8 O3 53.9(5) 2_665 . . . ?
C5 C7 C8 O4 -124.8(3) 2_665 . . . ?
C6 C7 C8 O3 -128.3(3) . . . . ?
C6 C7 C8 O4 53.0(5) . . . . ?
C7 C5 C6 F1 177.6(3) 2_665 . . . ?
C7 C5 C6 C7 0.7(6) 2_665 . . . ?
C10 N00B C9 O5 3.5(8) . . . . ?
C11 N00B C9 O5 -177.0(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_exp_5969
_audit_block_doi                 10.5517/ccdc.csd.cc2d4fss
_database_code_depnum_ccdc_archive 'CCDC 2208805'
loop_
_audit_author_name
_audit_author_address
'Zhi-Qing Liu'
;Guangdong University of Technology
China
;
_audit_update_record             
;
2022-09-22 deposited with the CCDC.	2022-11-29 downloaded from the CCDC.
;
_audit_creation_date             2022-09-05
_audit_creation_method           
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C4 F O2 S), 4(H4 N), H2 O'
_chemical_formula_sum            'C8 H18 F2 N4 O5 S2'
_chemical_formula_weight         352.38
_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'
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      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                   16.6143(5)
_cell_length_b                   10.5019(3)
_cell_length_c                   8.8282(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.725(4)
_cell_angle_gamma                90
_cell_volume                     1496.38(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8953
_cell_measurement_temperature    240.01(10)
_cell_measurement_theta_max      29.7930
_cell_measurement_theta_min      3.7190
_shelx_estimated_absorpt_T_max   0.961
_shelx_estimated_absorpt_T_min   0.961
_exptl_absorpt_coefficient_mu    0.404
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.61a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       cube
_exptl_crystal_F_000             736
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.865
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            14979
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.865
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.885
_diffrn_reflns_theta_min         3.525
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      240.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.6525
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.865
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -30.00  40.00   1.00   10.00    --   10.66 -77.00-150.00   70
  2  ω    -48.00   2.00   1.00   10.00    --  -11.13 -57.00 -30.00   50
  3  ω     14.00  66.00   1.00   10.00    --   10.66  38.00 150.00   52
  4  ω    -33.00  17.00   1.00   10.00    --  -11.13 -77.00-150.00   50
  5  ω    -40.00  20.00   1.00   10.00    --  -11.13  77.00  90.00   60
  6  ω    -48.00  41.00   1.00   10.00    --  -11.13  19.00  30.00   89
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0297481000
_diffrn_orient_matrix_UB_12      0.0154691000
_diffrn_orient_matrix_UB_13      -0.0695221000
_diffrn_orient_matrix_UB_21      0.0151452000
_diffrn_orient_matrix_UB_22      0.0633613000
_diffrn_orient_matrix_UB_23      0.0045022000
_diffrn_orient_matrix_UB_31      0.0285445000
_diffrn_orient_matrix_UB_32      -0.0175894000
_diffrn_orient_matrix_UB_33      -0.0446335000
_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_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3345
_reflns_number_total             3744
_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 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.510
_refine_diff_density_min         -0.498
_refine_diff_density_rms         0.053
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3744
_refine_ls_number_restraints     15
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0306
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0408P)²+0.5988P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0802
_refine_ls_wR_factor_ref         0.0841
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 H4A-H4B \\sim H4A-H4C \\sim H4A-H4D \\sim H4B-H4C \\sim H4B-H4D \\sim H4C-H4D
 with sigma of 0.02
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_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
S1 S 0.44821(2) -0.17115(3) -0.30815(4) 0.02129(10) Uani 1 1 d . . . . .
F1 F 0.33975(5) -0.07053(8) -0.10742(10) 0.0285(2) Uani 1 1 d . . . . .
O1 O 0.35839(7) 0.01207(11) 0.26177(12) 0.0315(2) Uani 1 1 d . . . . .
O2 O 0.33197(6) 0.17758(9) 0.09839(13) 0.0268(2) Uani 1 1 d . . . . .
C1 C 0.37142(8) 0.07797(12) 0.15370(15) 0.0194(3) Uani 1 1 d . . . . .
C2 C 0.44011(7) 0.03826(12) 0.07729(15) 0.0173(2) Uani 1 1 d . . . . .
C3 C 0.42103(7) -0.03609(12) -0.05534(15) 0.0180(2) Uani 1 1 d . . . . .
C4 C 0.47762(7) -0.07763(12) -0.13862(14) 0.0169(2) Uani 1 1 d . . . . .
S2 S 0.07246(2) 0.15795(3) 0.31337(4) 0.02082(10) Uani 1 1 d . . . . .
F003 F 0.16404(5) 0.05236(9) 0.08631(10) 0.0297(2) Uani 1 1 d . . . . .
O4 O 0.12246(6) -0.01253(9) -0.29194(12) 0.0258(2) Uani 1 1 d . . . . .
O3 O 0.15200(6) -0.18707(9) -0.14556(12) 0.0268(2) Uani 1 1 d . . . . .
C5 C 0.11410(7) -0.08287(12) -0.18427(15) 0.0180(2) Uani 1 1 d . . . . .
C6 C 0.05296(7) -0.04235(12) -0.09010(15) 0.0171(2) Uani 1 1 d . . . . .
C7 C 0.08123(7) 0.02696(12) 0.04533(15) 0.0186(2) Uani 1 1 d . . . . .
C8 C 0.03189(7) 0.07179(12) 0.14089(14) 0.0170(2) Uani 1 1 d . . . . .
N2 N 0.24045(8) 0.18883(14) -0.22798(18) 0.0277(3) Uani 1 1 d . . . . .
N1 N 0.44574(9) 0.37573(13) 0.07069(16) 0.0276(3) Uani 1 1 d . . . . .
N3 N 0.03872(9) -0.36577(13) -0.07876(16) 0.0257(3) Uani 1 1 d . . . . .
N4 N 0.25798(9) -0.2365(2) 0.1590(2) 0.0487(5) Uani 1 1 d . . . . .
O5 O 0.25258(9) 0.01136(18) -0.53112(19) 0.0610(5) Uani 1 1 d . . . . .
H2A H 0.2693(13) 0.1805(18) -0.130(3) 0.038(5) Uiso 1 1 d . . . . .
H2B H 0.2707(12) 0.235(2) -0.281(2) 0.043(5) Uiso 1 1 d . . . . .
H1A H 0.4853(15) 0.346(2) 0.153(3) 0.053(6) Uiso 1 1 d . . . . .
H1B H 0.4029(14) 0.322(2) 0.064(3) 0.050(6) Uiso 1 1 d . . . . .
H1C H 0.4635(12) 0.3686(19) -0.015(3) 0.040(5) Uiso 1 1 d . . . . .
H1D H 0.4331(13) 0.454(2) 0.085(3) 0.048(6) Uiso 1 1 d . . . . .
H2C H 0.1936(14) 0.228(2) -0.227(2) 0.048(6) Uiso 1 1 d . . . . .
H2D H 0.2249(13) 0.116(2) -0.272(3) 0.051(6) Uiso 1 1 d . . . . .
H3A H 0.0249(13) -0.350(2) 0.006(3) 0.045(6) Uiso 1 1 d . . . . .
H3B H 0.0791(13) -0.3086(19) -0.089(2) 0.040(5) Uiso 1 1 d . . . . .
H3C H -0.0054(16) -0.359(2) -0.157(3) 0.066(7) Uiso 1 1 d . . . . .
H3D H 0.0591(14) -0.441(2) -0.080(3) 0.056(6) Uiso 1 1 d . . . . .
H4A H 0.2285(12) -0.2133(19) 0.072(2) 0.042(5) Uiso 1 1 d D . . . .
H4B H 0.2254(12) -0.260(2) 0.223(2) 0.054(6) Uiso 1 1 d D . . . .
H4C H 0.2933(14) -0.290(2) 0.157(3) 0.079(9) Uiso 1 1 d D . . . .
H4D H 0.285(2) -0.165(3) 0.210(4) 0.24(3) Uiso 1 1 d D . . . .
H5A H 0.204(2) 0.040(3) -0.580(3) 0.091(10) Uiso 1 1 d . . . . .
H5B H 0.2776(19) 0.000(3) -0.600(4) 0.095(10) Uiso 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
S1 C4 1.7597(13) . ?
F1 C3 1.3679(14) . ?
O1 C1 1.2386(16) . ?
O2 C1 1.2690(16) . ?
C1 C2 1.5154(16) . ?
C2 C3 1.3803(18) . ?
C2 C4 1.4075(17) 3_655 ?
C3 C4 1.3938(16) . ?
S2 C8 1.7620(13) . ?
F003 C7 1.3633(13) . ?
O4 C5 1.2374(16) . ?
O3 C5 1.2684(16) . ?
C5 C6 1.5181(16) . ?
C6 C7 1.3833(18) . ?
C6 C8 1.4086(16) 3 ?
C7 C8 1.3905(16) . ?
N2 H2A 0.89(2) . ?
N2 H2B 0.90(2) . ?
N2 H2C 0.88(2) . ?
N2 H2D 0.87(2) . ?
N1 H1A 0.91(2) . ?
N1 H1B 0.90(2) . ?
N1 H1C 0.88(2) . ?
N1 H1D 0.86(2) . ?
N3 H3A 0.85(2) . ?
N3 H3B 0.92(2) . ?
N3 H3C 0.88(3) . ?
N3 H3D 0.86(3) . ?
N4 H4A 0.842(18) . ?
N4 H4B 0.906(18) . ?
N4 H4C 0.82(2) . ?
N4 H4D 0.94(2) . ?
O5 H5A 0.87(3) . ?
O5 H5B 0.82(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 C1 O2 126.04(12) . . ?
O1 C1 C2 118.48(12) . . ?
O2 C1 C2 115.49(11) . . ?
C3 C2 C1 119.19(11) . . ?
C3 C2 C4 119.94(11) . 3_655 ?
C4 C2 C1 120.87(11) 3_655 . ?
F1 C3 C2 116.39(10) . . ?
F1 C3 C4 118.40(11) . . ?
C2 C3 C4 125.21(11) . . ?
C2 C4 S1 122.65(9) 3_655 . ?
C3 C4 S1 122.50(10) . . ?
C3 C4 C2 114.85(11) . 3_655 ?
O4 C5 O3 125.66(11) . . ?
O4 C5 C6 117.71(11) . . ?
O3 C5 C6 116.63(11) . . ?
C7 C6 C5 119.13(11) . . ?
C7 C6 C8 119.97(11) . 3 ?
C8 C6 C5 120.88(11) 3 . ?
F003 C7 C6 116.53(10) . . ?
F003 C7 C8 118.41(11) . . ?
C6 C7 C8 125.06(11) . . ?
C6 C8 S2 122.45(9) 3 . ?
C7 C8 S2 122.58(9) . . ?
C7 C8 C6 114.97(11) . 3 ?
H2A N2 H2B 108.4(18) . . ?
H2A N2 H2C 108.2(19) . . ?
H2A N2 H2D 112.8(19) . . ?
H2B N2 H2C 110.7(18) . . ?
H2B N2 H2D 112.5(18) . . ?
H2C N2 H2D 104.2(19) . . ?
H1A N1 H1B 104.6(19) . . ?
H1A N1 H1C 109.4(19) . . ?
H1A N1 H1D 111(2) . . ?
H1B N1 H1C 108.2(18) . . ?
H1B N1 H1D 112.8(19) . . ?
H1C N1 H1D 110.4(19) . . ?
H3A N3 H3B 108.1(18) . . ?
H3A N3 H3C 109(2) . . ?
H3A N3 H3D 112(2) . . ?
H3B N3 H3C 111(2) . . ?
H3B N3 H3D 107.3(18) . . ?
H3C N3 H3D 108(2) . . ?
H4A N4 H4B 110.1(16) . . ?
H4A N4 H4C 116.3(19) . . ?
H4A N4 H4D 109(2) . . ?
H4B N4 H4C 111.4(18) . . ?
H4B N4 H4D 102.2(18) . . ?
H4C N4 H4D 107.3(19) . . ?
H5A O5 H5B 105(3) . . ?

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
F1 C3 C4 S1 0.52(17) . . . . ?
F1 C3 C4 C2 -179.92(11) . . . 3_655 ?
O1 C1 C2 C3 94.33(16) . . . . ?
O1 C1 C2 C4 -86.54(16) . . . 3_655 ?
O2 C1 C2 C3 -85.37(15) . . . . ?
O2 C1 C2 C4 93.76(15) . . . 3_655 ?
C1 C2 C3 F1 -0.95(18) . . . . ?
C1 C2 C3 C4 178.93(12) . . . . ?
C2 C3 C4 S1 -179.37(10) . . . . ?
C2 C3 C4 C2 0.2(2) . . . 3_655 ?
C4 C2 C3 F1 179.91(11) 3_655 . . . ?
C4 C2 C3 C4 -0.2(2) 3_655 . . . ?
F003 C7 C8 S2 -0.85(17) . . . . ?
F003 C7 C8 C6 179.60(11) . . . 3 ?
O4 C5 C6 C7 -93.45(15) . . . . ?
O4 C5 C6 C8 85.02(16) . . . 3 ?
O3 C5 C6 C7 86.90(15) . . . . ?
O3 C5 C6 C8 -94.62(15) . . . 3 ?
C5 C6 C7 F003 -1.10(18) . . . . ?
C5 C6 C7 C8 178.87(12) . . . . ?
C6 C7 C8 S2 179.18(10) . . . . ?
C6 C7 C8 C6 -0.4(2) . . . 3 ?
C8 C6 C7 F003 -179.59(11) 3 . . . ?
C8 C6 C7 C8 0.4(2) 3 . . . ?

_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 1.244
_oxdiff_exptl_absorpt_empirical_full_min 0.808
