# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_ad_14
_database_code_depnum_ccdc_archive 'CCDC 1939457'
loop_
_audit_author_name
_audit_author_address
'Anna Dolega'
;Gdansk University of Technology
Poland
;
_audit_update_record             
;
2020-07-20 deposited with the CCDC.	2020-07-22 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT430_ad_14               
;
PROBLEM: Short Inter D...A Contact  O6       ..O10      .       2.71 Ang.
RESPONSE: the H atoms of O10 were not visible in difference maps and were not included in the model
;
_vrf_PLAT041_ad_14               
;
PROBLEM: Calc. and Reported SumFormula    Strings  Differ     Please Check
RESPONSE: the H atoms of O10 were not visible in difference maps and were not included in the model, yet they are present in crystals
;
_vrf_PLAT043_ad_14               
;
PROBLEM: Calculated and Reported Mol. Weight Differ by ..       1.49 Check
RESPONSE: the H atoms of O10 were not visible in difference maps and were not included in the model
;
# Added during the CSD deposition process: Monday 20 July 2020 05:54 PM
# end Validation Reply Form


_audit_creation_date             2020-06-18T10:39:50-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C24 H43.48 N4 O18.74 S2 U2'
_chemical_formula_weight         1228.13

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.908(2)
_cell_length_b                   14.714(4)
_cell_length_c                   15.163(6)
_cell_angle_alpha                90
_cell_angle_beta                 97.85(3)
_cell_angle_gamma                90
_cell_volume                     1968.8(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    16635
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      29.55

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.296
_exptl_crystal_size_min          0.188
_exptl_crystal_density_diffrn    2.069
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1161
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 3 -2 0.096
0 -3 2 0.092
-4 0 3 0.221
-1 -3 -4 0.094
0 2 3 0.089
-2 3 2 0.221
-5 1 -3 0.229
-1 -4 3 0.112
2 0 -1 0.271
1 4 -3 0.127
0 -2 -3 0.112


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    8.396
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
        Structure Analysis", published in
        F. R. Ahmed (Editor), "Crystallographic Computing",
        Munksgaard, Copenhagen (1970), 255 - 270
;
_exptl_absorpt_correction_T_min  0.5705
_exptl_absorpt_correction_T_max  0.7186

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0282
_diffrn_reflns_number            10622
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.712
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_coverage         0
_reflns_number_total             3856
_reflns_number_gt                3372
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_cell_refinement       
;
        X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        
;
        X-Area Integrate 1.72.0.0 (STOE, 2018)
        X-Area X-Red32 1.63.4.0 (STOE, 2017)
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image
processing, for the correction and scaling of reflection intensities and
        for outlier rejection, version 1.81, Darmstadt 2018
;

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0387P)²+6.8471P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3856
_refine_ls_number_parameters     243
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0353
_refine_ls_R_factor_gt           0.0285
_refine_ls_wR_factor_ref         0.0711
_refine_ls_wR_factor_gt          0.0678
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.539
_refine_diff_density_min         -0.964
_refine_diff_density_rms         0.148

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'
U U -9.6767 9.6646 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
U1 U 0.49992(2) 0.62752(2) 0.20989(2) 0.01580(8) Uani 1 1 d . . . . .
O3 O 0.2752(4) 0.5942(3) 0.0994(2) 0.0234(8) Uani 1 1 d . . . . .
O4 O 0.4621(4) 0.4988(2) 0.1069(2) 0.0219(8) Uani 1 1 d . . . . .
C1 C 0.3337(6) 0.5227(3) 0.0713(3) 0.0190(10) Uani 1 1 d . . . . .
O8 O 0.2944(4) 0.7381(3) 0.2084(3) 0.0302(9) Uani 1 1 d . . . . .
O7 O 0.4914(4) 0.7663(3) 0.3059(2) 0.0229(8) Uani 1 1 d . . . . .
O6 O 0.7424(4) 0.6557(3) 0.3053(3) 0.0320(9) Uani 1 1 d D . . . .
O5 O 0.7297(4) 0.5323(3) 0.2233(3) 0.0287(9) Uani 1 1 d . . . . .
O1 O 0.5723(4) 0.6940(2) 0.1277(2) 0.0236(8) Uani 1 1 d . . . . .
O2 O 0.4280(4) 0.5617(3) 0.2922(2) 0.0254(8) Uani 1 1 d . . . . .
N1 N 0.9958(5) 0.7598(3) 0.1309(3) 0.0196(8) Uani 1 1 d . . . . .
H1A H 1.075114 0.730848 0.158475 0.024 Uiso 1 1 calc R U . . .
H1B H 0.937159 0.791416 0.161718 0.024 Uiso 1 1 calc R U . . .
N2 N 1.0506(5) 0.7088(3) -0.0041(3) 0.0184(9) Uani 1 1 d . . . . .
H2D H 1.130516 0.679357 0.022091 0.022 Uiso 1 1 calc R U . . .
H2E H 1.027898 0.706924 -0.062442 0.022 Uiso 1 1 calc R U . . .
C12 C 0.9649(5) 0.7557(3) 0.0440(3) 0.0180(10) Uani 1 1 d . . . . .
C9 C 0.6228(5) 0.9453(3) 0.0330(3) 0.0178(10) Uani 1 1 d . . . . .
C6 C 0.2871(7) 0.8752(4) 0.2926(4) 0.0355(14) Uani 1 1 d . . . . .
H6A H 0.361374 0.913163 0.329401 0.053 Uiso 1 1 calc R U . . .
H6B H 0.203759 0.860245 0.326169 0.053 Uiso 1 1 calc R U . . .
H6C H 0.247143 0.908317 0.238403 0.053 Uiso 1 1 calc R U . . .
C5 C 0.3613(6) 0.7900(4) 0.2683(3) 0.0232(11) Uani 1 1 d . . . . .
C2 C 0.2491(6) 0.4710(4) -0.0055(3) 0.0256(12) Uani 1 1 d . . . . .
H2A H 0.26445 0.500364 -0.061544 0.038 Uiso 1 1 calc R U . . .
H2B H 0.140803 0.470382 0.000058 0.038 Uiso 1 1 calc R U . . .
H2C H 0.287042 0.408406 -0.004927 0.038 Uiso 1 1 calc R U . . .
S1 S 0.80882(14) 0.81252(9) -0.01444(8) 0.0200(3) Uani 1 1 d . . . . .
C4 C 0.9777(6) 0.5822(5) 0.2865(4) 0.0360(15) Uani 1 1 d . . . . .
H4A H 1.016234 0.584843 0.229035 0.054 Uiso 1 1 calc R U . . .
H4B H 1.00743 0.524395 0.315921 0.054 Uiso 1 1 calc R U . . .
H4C H 1.020302 0.632632 0.324141 0.054 Uiso 1 1 calc R U . . .
C3 C 0.8082(6) 0.5895(4) 0.2719(3) 0.0281(12) Uani 1 1 d . . . . .
C10 C 0.7500(6) 0.8846(3) 0.0737(3) 0.0197(10) Uani 1 1 d . . . . .
H10A H 0.715518 0.846296 0.120664 0.024 Uiso 1 1 calc R U . . .
H10B H 0.836587 0.921921 0.101018 0.024 Uiso 1 1 calc R U . . .
C8 C 0.4741(5) 0.9182(3) 0.0386(3) 0.0176(10) Uani 1 1 d . . . . .
H8 H 0.457326 0.861302 0.065152 0.021 Uiso 1 1 calc R U . . .
C7 C 0.3500(5) 0.9716(3) 0.0068(3) 0.0171(10) Uani 1 1 d . . . . .
C11 C 0.1916(6) 0.9393(4) 0.0163(4) 0.0230(11) Uani 1 1 d . . . . .
H11A H 0.140836 0.984796 0.048921 0.035 Uiso 1 1 calc R U . . .
H11B H 0.197579 0.881601 0.048898 0.035 Uiso 1 1 calc R U . . .
H11C H 0.134008 0.930427 -0.042949 0.035 Uiso 1 1 calc R U . . .
O9 O 0.8837(6) 0.8347(4) 0.2764(3) 0.0507(13) Uani 1 1 d DG . . . .
H9A H 0.864025 0.804204 0.320922 0.076 Uiso 1 1 d G U . . .
H9B H 0.865042 0.890472 0.284139 0.076 Uiso 1 1 d G U . . .
O10 O 0.8543(19) 0.7697(7) 0.4385(4) 0.083(8) Uani 0.370(18) 1 d D . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
U1 O2 1.768(4) . ?
U1 O1 1.774(4) . ?
U1 O8 2.447(4) . ?
U1 O4 2.448(4) . ?
U1 O5 2.465(4) . ?
U1 O6 2.465(4) . ?
U1 O3 2.478(4) . ?
U1 O7 2.515(4) . ?
U1 C3 2.834(5) . ?
U1 C1 2.853(5) . ?
U1 C5 2.885(5) . ?
O3 C1 1.273(6) . ?
O4 C1 1.246(6) . ?
C1 C2 1.504(7) . ?
O8 C5 1.270(6) . ?
O7 C5 1.269(6) . ?
O6 C3 1.276(7) . ?
O5 C3 1.265(7) . ?
N1 C12 1.311(6) . ?
N1 H1A 0.88 . ?
N1 H1B 0.88 . ?
N2 C12 1.321(6) . ?
N2 H2D 0.88 . ?
N2 H2E 0.88 . ?
C12 S1 1.756(5) . ?
C9 C8 1.397(7) . ?
C9 C7 1.399(7) 3_675 ?
C9 C10 1.507(7) . ?
C6 C5 1.487(7) . ?
C6 H6A 0.98 . ?
C6 H6B 0.98 . ?
C6 H6C 0.98 . ?
C2 H2A 0.98 . ?
C2 H2B 0.98 . ?
C2 H2C 0.98 . ?
S1 C10 1.837(5) . ?
C4 C3 1.500(7) . ?
C4 H4A 0.98 . ?
C4 H4B 0.98 . ?
C4 H4C 0.98 . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C8 C7 1.388(7) . ?
C8 H8 0.95 . ?
C7 C11 1.514(7) . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
O9 H9A 0.849 . ?
O9 H9B 0.8483 . ?

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
O2 U1 O1 179.72(17) . . ?
O2 U1 O8 91.61(17) . . ?
O1 U1 O8 88.30(16) . . ?
O2 U1 O4 89.71(15) . . ?
O1 U1 O4 90.57(14) . . ?
O8 U1 O4 118.07(12) . . ?
O2 U1 O5 90.40(16) . . ?
O1 U1 O5 89.65(16) . . ?
O8 U1 O5 171.92(13) . . ?
O4 U1 O5 69.75(13) . . ?
O2 U1 O6 92.91(16) . . ?
O1 U1 O6 86.91(16) . . ?
O8 U1 O6 119.22(13) . . ?
O4 U1 O6 122.53(13) . . ?
O5 U1 O6 52.84(13) . . ?
O2 U1 O3 91.85(15) . . ?
O1 U1 O3 88.35(15) . . ?
O8 U1 O3 65.85(12) . . ?
O4 U1 O3 52.23(12) . . ?
O5 U1 O3 121.91(12) . . ?
O6 U1 O3 172.92(12) . . ?
O2 U1 O7 89.65(15) . . ?
O1 U1 O7 90.09(15) . . ?
O8 U1 O7 51.97(12) . . ?
O4 U1 O7 169.99(11) . . ?
O5 U1 O7 120.24(12) . . ?
O6 U1 O7 67.48(12) . . ?
O3 U1 O7 117.81(11) . . ?
O2 U1 C3 94.91(17) . . ?
O1 U1 C3 85.02(17) . . ?
O8 U1 C3 145.48(15) . . ?
O4 U1 C3 95.86(15) . . ?
O5 U1 C3 26.46(15) . . ?
O6 U1 C3 26.71(15) . . ?
O3 U1 C3 147.37(14) . . ?
O7 U1 C3 94.15(14) . . ?
O2 U1 C1 91.28(15) . . ?
O1 U1 C1 88.98(15) . . ?
O8 U1 C1 92.31(13) . . ?
O4 U1 C1 25.78(13) . . ?
O5 U1 C1 95.47(14) . . ?
O6 U1 C1 148.02(14) . . ?
O3 U1 C1 26.46(13) . . ?
O7 U1 C1 144.27(13) . . ?
C3 U1 C1 121.32(16) . . ?
O2 U1 C5 91.48(17) . . ?
O1 U1 C5 88.32(16) . . ?
O8 U1 C5 25.94(13) . . ?
O4 U1 C5 144.01(13) . . ?
O5 U1 C5 146.18(14) . . ?
O6 U1 C5 93.34(14) . . ?
O3 U1 C5 91.78(13) . . ?
O7 U1 C5 26.05(13) . . ?
C3 U1 C5 119.84(16) . . ?
C1 U1 C5 118.24(14) . . ?
C1 O3 U1 93.4(3) . . ?
C1 O4 U1 95.6(3) . . ?
O4 C1 O3 118.8(4) . . ?
O4 C1 C2 121.7(5) . . ?
O3 C1 C2 119.5(5) . . ?
O4 C1 U1 58.7(3) . . ?
O3 C1 U1 60.1(3) . . ?
C2 C1 U1 176.8(4) . . ?
C5 O8 U1 96.7(3) . . ?
C5 O7 U1 93.5(3) . . ?
C3 O6 U1 93.0(3) . . ?
C3 O5 U1 93.3(3) . . ?
C12 N1 H1A 120 . . ?
C12 N1 H1B 120 . . ?
H1A N1 H1B 120 . . ?
C12 N2 H2D 120 . . ?
C12 N2 H2E 120 . . ?
H2D N2 H2E 120 . . ?
N1 C12 N2 121.5(4) . . ?
N1 C12 S1 121.9(4) . . ?
N2 C12 S1 116.6(4) . . ?
C8 C9 C7 119.8(4) . 3_675 ?
C8 C9 C10 118.2(5) . . ?
C7 C9 C10 122.0(4) 3_675 . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
O7 C5 O8 117.8(5) . . ?
O7 C5 C6 122.0(5) . . ?
O8 C5 C6 120.2(5) . . ?
O7 C5 U1 60.5(3) . . ?
O8 C5 U1 57.4(3) . . ?
C6 C5 U1 176.6(4) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C12 S1 C10 101.1(2) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O5 C3 O6 119.4(5) . . ?
O5 C3 C4 120.2(5) . . ?
O6 C3 C4 120.2(5) . . ?
O5 C3 U1 60.3(3) . . ?
O6 C3 U1 60.3(3) . . ?
C4 C3 U1 166.8(4) . . ?
C9 C10 S1 108.5(3) . . ?
C9 C10 H10A 110 . . ?
S1 C10 H10A 110 . . ?
C9 C10 H10B 110 . . ?
S1 C10 H10B 110 . . ?
H10A C10 H10B 108.4 . . ?
C7 C8 C9 122.3(5) . . ?
C7 C8 H8 118.9 . . ?
C9 C8 H8 118.9 . . ?
C8 C7 C9 117.9(4) . 3_675 ?
C8 C7 C11 119.8(4) . . ?
C9 C7 C11 122.3(4) 3_675 . ?
C7 C11 H11A 109.5 . . ?
C7 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C7 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
H9A O9 H9B 109.6 . . ?

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
U1 O4 C1 O3 -1.8(5) . . . . ?
U1 O4 C1 C2 176.3(4) . . . . ?
U1 O3 C1 O4 1.7(5) . . . . ?
U1 O3 C1 C2 -176.4(4) . . . . ?
U1 O7 C5 O8 3.1(5) . . . . ?
U1 O7 C5 C6 -177.2(5) . . . . ?
U1 O8 C5 O7 -3.2(5) . . . . ?
U1 O8 C5 C6 177.1(5) . . . . ?
N1 C12 S1 C10 10.7(5) . . . . ?
N2 C12 S1 C10 -168.9(4) . . . . ?
U1 O5 C3 O6 12.3(5) . . . . ?
U1 O5 C3 C4 -164.7(5) . . . . ?
U1 O6 C3 O5 -12.3(5) . . . . ?
U1 O6 C3 C4 164.7(5) . . . . ?
C8 C9 C10 S1 96.6(5) . . . . ?
C7 C9 C10 S1 -85.7(5) 3_675 . . . ?
C12 S1 C10 C9 175.2(4) . . . . ?
C7 C9 C8 C7 -0.8(8) 3_675 . . . ?
C10 C9 C8 C7 177.0(5) . . . . ?
C9 C8 C7 C9 0.8(8) . . . 3_675 ?
C9 C8 C7 C11 -178.9(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
_geom_hbond_publ_flag
N1 H1A O8 0.88 2 2.776(6) 146.5 1_655 yes
N1 H1B O9 0.88 1.97 2.771(6) 150.7 . yes
N2 H2D O3 0.88 2.05 2.906(5) 165.2 1_655 yes
N2 H2E O7 0.88 2.02 2.880(6) 166.4 4_675 yes
O9 H9A O6 0.85 2.44 2.977(7) 122.3 . yes
O9 H9A O10 0.85 1.87 2.684(5) 160.9 . yes
O9 H9B O4 0.85 2.64 3.192(6) 124.3 2_655 yes
O9 H9B O5 0.85 2.25 3.078(7) 165.9 2_655 yes

####################################################################### 
# 
# 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_eg1_2019
_database_code_depnum_ccdc_archive 'CCDC 1944695'
loop_
_audit_author_name
_audit_author_address
'Anna Dolega'
;Gdansk University of Technology
Poland
;
_audit_update_record             
;
2020-06-29 deposited with the CCDC.	2020-07-22 downloaded from the CCDC.
;

_audit_creation_date             2020-06-25T11:26:04-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C12 H20 Cl2 N4 S2'
_chemical_formula_weight         355.34

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.6982(4)
_cell_length_b                   6.3203(5)
_cell_length_c                   11.4318(8)
_cell_angle_alpha                90.470(6)
_cell_angle_beta                 93.651(5)
_cell_angle_gamma                99.991(6)
_cell_volume                     404.56(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5065
_cell_measurement_theta_min      3.27
_cell_measurement_theta_max      29.58

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.188
_exptl_crystal_size_mid          0.132
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             186
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 -4 0.026
-1 2 -2 0.077
2 -3 1 0.081
-3 -3 -2 0.127
-2 2 -1 0.087
3 1 2 0.061
-1 3 0 0.091
0 1 -4 0.062
-1 0 3 0.024


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.655
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
        Structure Analysis", published in
        F. R. Ahmed (Editor), "Crystallographic Computing",
        Munksgaard, Copenhagen (1970), 255 - 270
;
_exptl_absorpt_correction_T_min  0.886
_exptl_absorpt_correction_T_max  0.9709

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_reflns_av_R_equivalents  0.0366
_diffrn_reflns_av_unetI/netI     0.0388
_diffrn_reflns_number            3775
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.274
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_Friedel_coverage         0
_reflns_number_total             1581
_reflns_number_gt                1322
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_cell_refinement       
;
        X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        
;
        X-Area Integrate 1.72.0.0 (STOE, 2018)
        X-Area X-Red32 1.63.4.0 (STOE, 2017)
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image
processing, for the correction and scaling of reflection intensities and
        for outlier rejection, version 1.81, Darmstadt 2018
;

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0589P)²+0.0575P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         1581
_refine_ls_number_parameters     108
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0349
_refine_ls_wR_factor_ref         0.0925
_refine_ls_wR_factor_gt          0.0884
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.382
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.073

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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'
N N 0.0061 0.0033 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
Cl1 Cl 0.88226(8) 0.78671(8) 0.88909(5) 0.01832(17) Uani 1 1 d . . . . .
S1 S 0.33423(9) 0.38850(9) 0.79158(5) 0.01943(18) Uani 1 1 d . . . . .
N2 N 0.4225(3) -0.0040(3) 0.84708(17) 0.0191(4) Uani 1 1 d . . . . .
H2A H 0.521(5) -0.087(5) 0.869(2) 0.030(7) Uiso 1 1 d . . . . .
H2B H 0.274(5) -0.055(5) 0.840(2) 0.031(8) Uiso 1 1 d . . . . .
N1 N 0.7107(3) 0.2867(3) 0.90394(17) 0.0197(4) Uani 1 1 d . . . . .
H1A H 0.801(5) 0.209(5) 0.940(3) 0.036(8) Uiso 1 1 d . . . . .
H1B H 0.760(5) 0.427(5) 0.892(2) 0.036(8) Uiso 1 1 d . . . . .
C1 C 0.5002(4) 0.2034(4) 0.85380(18) 0.0160(5) Uani 1 1 d . . . . .
C3 C 0.0593(4) 0.3642(4) 0.58853(19) 0.0170(5) Uani 1 1 d . . . . .
C4 C 0.1567(4) 0.3533(4) 0.4797(2) 0.0173(5) Uani 1 1 d . . . . .
C5 C 0.0921(4) 0.4901(4) 0.39351(19) 0.0178(5) Uani 1 1 d . . . . .
H5 H 0.154571 0.483598 0.318718 0.021 Uiso 1 1 calc R U . . .
C2 C 0.1198(4) 0.2221(4) 0.6882(2) 0.0201(5) Uani 1 1 d . . . . .
H2C H 0.190115 0.101567 0.657868 0.024 Uiso 1 1 calc R U . . .
H2D H -0.026223 0.161804 0.727548 0.024 Uiso 1 1 calc R U . . .
C6 C 0.3276(4) 0.2029(4) 0.4548(2) 0.0242(5) Uani 1 1 d . . . . .
H6A H 0.473641 0.24114 0.506082 0.036 Uiso 1 1 calc R U . . .
H6B H 0.367427 0.215206 0.372731 0.036 Uiso 1 1 calc R U . . .
H6C H 0.252442 0.054753 0.469477 0.036 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C1 1.755(2) . ?
S1 C2 1.829(2) . ?
N2 C1 1.309(3) . ?
N1 C1 1.317(3) . ?
C3 C5 1.389(3) 2_566 ?
C3 C4 1.400(3) . ?
C3 C2 1.516(3) . ?
C4 C5 1.390(3) . ?
C4 C6 1.512(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
C1 S1 C2 102.96(11) . . ?
N2 C1 N1 122.4(2) . . ?
N2 C1 S1 122.00(17) . . ?
N1 C1 S1 115.56(17) . . ?
C5 C3 C4 119.69(19) 2_566 . ?
C5 C3 C2 119.26(19) 2_566 . ?
C4 C3 C2 121.04(19) . . ?
C5 C4 C3 117.16(19) . . ?
C5 C4 C6 120.2(2) . . ?
C3 C4 C6 122.6(2) . . ?
C3 C5 C4 123.1(2) 2_566 . ?
C3 C2 S1 107.51(15) . . ?

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
_geom_hbond_publ_flag
N2 H2A Cl1 0.86(3) 2.33(3) 3.146(2) 158(2) 1_545 yes
N2 H2B Cl1 0.85(3) 2.38(3) 3.200(2) 161(2) 1_445 yes
N1 H1A Cl1 0.86(3) 2.85(3) 3.472(2) 130(2) 1_545 yes
N1 H1A Cl1 0.86(3) 2.57(3) 3.2994(19) 143(3) 2_767 yes
N1 H1B Cl1 0.90(3) 2.26(3) 3.151(2) 172(3) . yes

####################################################################### 
# 
# 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_eg_7a
_database_code_depnum_ccdc_archive 'CCDC 1944697'
loop_
_audit_author_name
_audit_author_address
'Anna Dolega'
;Gdansk University of Technology
Poland
;
_audit_update_record             
;
2020-06-29 deposited with the CCDC.	2020-07-22 downloaded from the CCDC.
;

_audit_creation_date             2020-06-24T16:59:57-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C14 H18 Cl2 N4 S2'
_chemical_formula_weight         377.34

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_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                   8.3086(4)
_cell_length_b                   27.7798(16)
_cell_length_c                   15.6569(7)
_cell_angle_alpha                90
_cell_angle_beta                 104.734(3)
_cell_angle_gamma                90
_cell_volume                     3495.0(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5062
_cell_measurement_theta_min      2.2
_cell_measurement_theta_max      35.31

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.236
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.032
_exptl_crystal_density_diffrn    1.434
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1568
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -1 0 0.02
-2 1 3 0.028
2 -1 -3 0.034
-1 1 -3 0.058
1 -1 4 0.178
0 1 0 0.012


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.611
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
        Structure Analysis", published in
        F. R. Ahmed (Editor), "Crystallographic Computing",
        Munksgaard, Copenhagen (1970), 255 - 270
;
_exptl_absorpt_correction_T_min  0.9152
_exptl_absorpt_correction_T_max  0.9801

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_reflns_av_R_equivalents  0.0937
_diffrn_reflns_av_unetI/netI     0.0764
_diffrn_reflns_number            12501
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.639
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_Friedel_coverage         0
_reflns_number_total             3446
_reflns_number_gt                2200
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_cell_refinement       
;
        X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        
;
        X-Area Integrate 1.72.0.0 (STOE, 2018)
        X-Area X-Red32 1.63.4.0 (STOE, 2017)
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image
processing, for the correction and scaling of reflection intensities and
        for outlier rejection, version 1.81, Darmstadt 2018
;

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   mixed


#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0673P)²+16.5851P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3446
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1188
_refine_ls_R_factor_gt           0.067
_refine_ls_wR_factor_ref         0.1703
_refine_ls_wR_factor_gt          0.1438
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.667
_refine_diff_density_min         -0.418
_refine_diff_density_rms         0.103

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
Cl1 Cl 0.12139(14) -0.40597(4) 0.62319(9) 0.0307(3) Uani 1 1 d . . . . .
S2 S 0.08592(15) 0.04186(4) 0.63083(9) 0.0304(3) Uani 1 1 d . . . . .
Cl2 Cl 0.15118(17) 0.23495(5) 0.62622(9) 0.0387(4) Uani 1 1 d . . . . .
S1 S 0.09779(19) -0.21109(5) 0.59779(11) 0.0471(4) Uani 1 1 d . . . . .
N3 N 0.2581(5) 0.12427(18) 0.6340(3) 0.0295(10) Uani 1 1 d . . . . .
H3A H 0.261(6) 0.154(2) 0.630(3) 0.022(14) Uiso 1 1 d . . . . .
H3B H 0.339(8) 0.111(2) 0.643(4) 0.043(19) Uiso 1 1 d . . . . .
C12 C 0.2545(6) -0.11067(18) 0.7472(3) 0.0272(11) Uani 1 1 d . . . . .
C1 C 0.1063(6) -0.27336(18) 0.6062(3) 0.0282(11) Uani 1 1 d . . . . .
C14 C 0.1131(6) 0.10347(18) 0.6264(3) 0.0275(11) Uani 1 1 d . . . . .
N1 N 0.1982(7) -0.29598(17) 0.6747(3) 0.0388(12) Uani 1 1 d . . . . .
H1A H 0.176(9) -0.328(3) 0.684(5) 0.08(2) Uiso 1 1 d . . . . .
H1B H 0.241(7) -0.284(2) 0.722(4) 0.036(17) Uiso 1 1 d . . . . .
C13 C 0.2980(6) 0.01908(17) 0.6664(4) 0.0283(11) Uani 1 1 d . . . . .
H13A H 0.362244 0.029151 0.624126 0.034 Uiso 1 1 calc R U . . .
H13B H 0.353552 0.032251 0.725247 0.034 Uiso 1 1 calc R U . . .
C7 C 0.2592(6) -0.05909(17) 0.7455(3) 0.0261(11) Uani 1 1 d . . . . .
C8 C 0.2321(6) -0.03338(18) 0.8184(3) 0.0326(12) Uani 1 1 d . . . . .
H8 H 0.234505 0.000809 0.817823 0.039 Uiso 1 1 calc R U . . .
C2 C 0.2878(7) -0.19169(18) 0.6747(4) 0.0364(13) Uani 1 1 d . . . . .
H2A H 0.293484 -0.204442 0.734434 0.044 Uiso 1 1 calc R U . . .
H2B H 0.385692 -0.203553 0.655795 0.044 Uiso 1 1 calc R U . . .
N2 N 0.0136(6) -0.29799(16) 0.5402(3) 0.0330(10) Uani 1 1 d . . . . .
H2C H 0.015(7) -0.331(2) 0.546(4) 0.041(16) Uiso 1 1 d . . . . .
H2D H -0.037(6) -0.2839(19) 0.486(4) 0.032(14) Uiso 1 1 d . . . . .
C11 C 0.2193(6) -0.13323(18) 0.8228(3) 0.0334(12) Uani 1 1 d . . . . .
H11 H 0.213515 -0.167353 0.824867 0.04 Uiso 1 1 calc R U . . .
N4 N -0.0219(5) 0.13024(18) 0.6139(3) 0.0357(11) Uani 1 1 d . . . . .
H4A H -0.037(11) 0.160(3) 0.614(6) 0.11(3) Uiso 1 1 d . . . . .
H4B H -0.116(7) 0.120(2) 0.619(3) 0.032(14) Uiso 1 1 d . . . . .
C5 C 0.3195(6) -0.06197(19) 0.6021(4) 0.0345(12) Uani 1 1 d . . . . .
H5 H 0.339794 -0.046318 0.551922 0.041 Uiso 1 1 calc R U . . .
C3 C 0.2861(6) -0.13673(18) 0.6757(3) 0.0316(12) Uani 1 1 d . . . . .
C4 C 0.3181(6) -0.11329(18) 0.6061(4) 0.0335(12) Uani 1 1 d . . . . .
H4 H 0.340148 -0.131379 0.558862 0.04 Uiso 1 1 calc R U . . .
C6 C 0.2917(6) -0.03518(17) 0.6706(3) 0.0286(11) Uani 1 1 d . . . . .
C9 C 0.2024(7) -0.0568(2) 0.8898(4) 0.0407(13) Uani 1 1 d . . . . .
H9 H 0.187165 -0.03879 0.93875 0.049 Uiso 1 1 calc R U . . .
C10 C 0.1942(7) -0.1073(2) 0.8912(4) 0.0415(14) Uani 1 1 d . . . . .
H10 H 0.170986 -0.123213 0.940453 0.05 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
S2 C14 1.730(5) . ?
S2 C13 1.821(5) . ?
S1 C1 1.735(5) . ?
S1 C2 1.807(5) . ?
N3 C14 1.314(6) . ?
C12 C3 1.412(7) . ?
C12 C7 1.434(7) . ?
C12 C11 1.434(7) . ?
C1 N1 1.309(7) . ?
C1 N2 1.313(6) . ?
C14 N4 1.318(6) . ?
C13 C6 1.510(7) . ?
C7 C8 1.412(7) . ?
C7 C6 1.432(7) . ?
C8 C9 1.370(8) . ?
C2 C3 1.527(7) . ?
C11 C10 1.351(8) . ?
C5 C6 1.372(7) . ?
C5 C4 1.427(7) . ?
C3 C4 1.352(7) . ?
C9 C10 1.404(8) . ?

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
C14 S2 C13 103.3(2) . . ?
C1 S1 C2 103.6(2) . . ?
C3 C12 C7 119.1(5) . . ?
C3 C12 C11 123.3(5) . . ?
C7 C12 C11 117.7(4) . . ?
N1 C1 N2 119.9(5) . . ?
N1 C1 S1 123.0(4) . . ?
N2 C1 S1 117.1(4) . . ?
N3 C14 N4 119.4(5) . . ?
N3 C14 S2 123.9(4) . . ?
N4 C14 S2 116.7(4) . . ?
C6 C13 S2 108.6(3) . . ?
C8 C7 C6 122.0(4) . . ?
C8 C7 C12 118.7(5) . . ?
C6 C7 C12 119.4(4) . . ?
C9 C8 C7 121.2(5) . . ?
C3 C2 S1 107.2(3) . . ?
C10 C11 C12 121.8(5) . . ?
C6 C5 C4 120.2(5) . . ?
C4 C3 C12 120.4(5) . . ?
C4 C3 C2 118.0(5) . . ?
C12 C3 C2 121.6(5) . . ?
C3 C4 C5 121.5(5) . . ?
C5 C6 C7 119.5(5) . . ?
C5 C6 C13 119.5(5) . . ?
C7 C6 C13 120.9(4) . . ?
C8 C9 C10 120.4(5) . . ?
C11 C10 C9 120.2(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
_geom_hbond_publ_flag
N3 H3A Cl2 0.84(5) 2.42(5) 3.194(5) 155(4) . yes
N3 H3B Cl1 0.76(6) 2.49(6) 3.179(5) 153(6) 3 yes
N1 H1A Cl1 0.92(8) 2.37(8) 3.183(5) 147(6) . yes
N1 H1B Cl2 0.81(6) 2.38(6) 3.168(5) 167(5) 4_546 yes
N2 H2C Cl1 0.91(6) 2.46(6) 3.301(5) 153(5) . yes
N2 H2D Cl2 0.93(5) 2.23(6) 3.149(5) 167(4) 5_556 yes
N4 H4A Cl2 0.83(9) 2.59(9) 3.229(5) 135(8) . yes
N4 H4B Cl1 0.86(6) 2.31(6) 3.168(5) 176(5) 3_455 yes

####################################################################### 
# 
# 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_ad_15
_database_code_depnum_ccdc_archive 'CCDC 1939458'
loop_
_audit_author_name
_audit_author_address
'Anna Dolega'
;Gdansk University of Technology
Poland
;
_audit_update_record             
;
2020-06-29 deposited with the CCDC.	2020-07-22 downloaded from the CCDC.
;

_audit_creation_date             2020-06-18T11:42:19-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C16 H26 N4 O4 S2'
_chemical_formula_moiety         'C12 H20 N4 S2, 2(C2 H3 O2)'
_chemical_formula_weight         402.53

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.2940(2)
_cell_length_b                   13.8446(4)
_cell_length_c                   16.1184(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.793(2)
_cell_angle_gamma                90
_cell_volume                     2069.44(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    15768
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      29.44

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.292
_exptl_crystal_size_min          0.159
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             856
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 -4 0 0.095
0 -3 1 0.079
2 2 -3 0.195
0 3 -1 0.08
-2 4 1 0.163
2 0 -1 0.211
4 0 1 0.204
0 1 4 0.132
0 -1 -4 0.129
-4 -1 -3 0.279
-2 1 4 0.222
-1 -4 2 0.099


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.285
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
        Structure Analysis", published in
        F. R. Ahmed (Editor), "Crystallographic Computing",
        Munksgaard, Copenhagen (1970), 255 - 270
;
_exptl_absorpt_correction_T_min  0.8384
_exptl_absorpt_correction_T_max  0.9391

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0211
_diffrn_reflns_number            14953
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.929
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_coverage         0
_reflns_number_total             4057
_reflns_number_gt                3488
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_cell_refinement       
;
        X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        
;
        X-Area Integrate 1.72.0.0 (STOE, 2018)
        X-Area X-Red32 1.63.4.0 (STOE, 2017)
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image
processing, for the correction and scaling of reflection intensities and
        for outlier rejection, version 1.81, Darmstadt 2018
;

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0399P)²+1.3504P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4057
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0894
_refine_ls_wR_factor_gt          0.0847
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.39
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.052

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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 0.11851(5) 0.59162(3) 0.78448(3) 0.02417(12) Uani 1 1 d . . . . .
S2 S 0.45278(5) 1.27029(3) 0.52114(3) 0.02598(12) Uani 1 1 d . . . . .
O1 O 0.12083(12) 0.66678(10) 0.46484(7) 0.0255(3) Uani 1 1 d . . . . .
O2 O -0.10971(13) 0.62853(10) 0.47527(8) 0.0275(3) Uani 1 1 d . . . . .
O3 O 0.67452(13) 0.55876(9) 0.70530(8) 0.0261(3) Uani 1 1 d . . . . .
O4 O 0.44633(14) 0.60221(10) 0.68659(10) 0.0369(3) Uani 1 1 d . . . . .
N4 N 0.62411(15) 1.39366(11) 0.60998(9) 0.0233(3) Uani 1 1 d . . . . .
H4C H 0.641405 1.446111 0.639826 0.028 Uiso 1 1 calc R U . . .
H4D H 0.694858 1.353593 0.60086 0.028 Uiso 1 1 calc R U . . .
N2 N -0.06287(15) 0.59953(11) 0.64624(9) 0.0230(3) Uani 1 1 d . . . . .
H2A H -0.083178 0.611379 0.593113 0.028 Uiso 1 1 calc R U . . .
H2B H -0.130804 0.578888 0.677392 0.028 Uiso 1 1 calc R U . . .
N1 N 0.17182(16) 0.64332(12) 0.63407(9) 0.0266(3) Uani 1 1 d . . . . .
H1A H 0.153725 0.655578 0.580827 0.032 Uiso 1 1 calc R U . . .
H1B H 0.259355 0.651661 0.657226 0.032 Uiso 1 1 calc R U . . .
N3 N 0.38390(15) 1.43248(11) 0.59085(10) 0.0255(3) Uani 1 1 d . . . . .
H3A H 0.39735 1.485559 0.620395 0.031 Uiso 1 1 calc R U . . .
H3B H 0.297218 1.417878 0.569208 0.031 Uiso 1 1 calc R U . . .
C13 C -0.00425(18) 0.64962(12) 0.43400(10) 0.0194(3) Uani 1 1 d . . . . .
C15 C 0.57332(17) 0.61795(13) 0.70780(10) 0.0199(3) Uani 1 1 d . . . . .
C1 C -0.01694(18) 0.51727(12) 0.91465(10) 0.0201(3) Uani 1 1 d . . . . .
C6 C 0.06830(18) 0.61262(12) 0.67891(10) 0.0201(3) Uani 1 1 d . . . . .
C7 C 0.55219(18) 1.08996(12) 0.52602(11) 0.0220(4) Uani 1 1 d . . . . .
C12 C 0.49294(18) 1.37520(12) 0.57910(11) 0.0207(3) Uani 1 1 d . . . . .
C3 C 0.07275(19) 0.41939(12) 1.02866(10) 0.0218(4) Uani 1 1 d . . . . .
H3 H 0.122954 0.36358 1.049056 0.026 Uiso 1 1 calc R U . . .
C2 C 0.05782(19) 0.43471(13) 0.94328(11) 0.0221(4) Uani 1 1 d . . . . .
C8 C 0.47974(19) 1.03042(13) 0.57907(11) 0.0251(4) Uani 1 1 d . . . . .
H8 H 0.4662 1.052302 0.633872 0.03 Uiso 1 1 calc R U . . .
C9 C 0.42663(19) 0.94041(13) 0.55490(11) 0.0240(4) Uani 1 1 d . . . . .
C4 C -0.04394(18) 0.53816(13) 0.82297(10) 0.0221(4) Uani 1 1 d . . . . .
H4A H -0.126059 0.583341 0.813978 0.027 Uiso 1 1 calc R U . . .
H4B H -0.068189 0.47761 0.792499 0.027 Uiso 1 1 calc R U . . .
C10 C 0.60016(19) 1.18883(13) 0.55587(12) 0.0259(4) Uani 1 1 d . . . . .
H10A H 0.690827 1.207736 0.531263 0.031 Uiso 1 1 calc R U . . .
H10B H 0.615913 1.189933 0.617208 0.031 Uiso 1 1 calc R U . . .
C14 C -0.0302(2) 0.65679(14) 0.34067(11) 0.0274(4) Uani 1 1 d . . . . .
H14A H -0.068092 0.721016 0.325856 0.041 Uiso 1 1 calc R U . . .
H14B H -0.100225 0.607518 0.321128 0.041 Uiso 1 1 calc R U . . .
H14C H 0.060727 0.64647 0.314498 0.041 Uiso 1 1 calc R U . . .
C5 C 0.1197(2) 0.36271(15) 0.88515(12) 0.0350(5) Uani 1 1 d . . . . .
H5A H 0.042085 0.336161 0.847842 0.053 Uiso 1 1 calc R U . . .
H5B H 0.16672 0.310274 0.917567 0.053 Uiso 1 1 calc R U . . .
H5C H 0.190687 0.394911 0.85228 0.053 Uiso 1 1 calc R U . . .
C11 C 0.3471(2) 0.87901(15) 0.61434(13) 0.0355(5) Uani 1 1 d . . . . .
H11A H 0.246703 0.871074 0.592833 0.053 Uiso 1 1 calc R U . . .
H11B H 0.349704 0.910609 0.668822 0.053 Uiso 1 1 calc R U . . .
H11C H 0.393345 0.815517 0.619929 0.053 Uiso 1 1 calc R U . . .
C16 C 0.6132(2) 0.71830(15) 0.74377(13) 0.0346(5) Uani 1 1 d . . . . .
H16A H 0.657795 0.711042 0.800244 0.052 Uiso 1 1 calc R U . . .
H16B H 0.52593 0.757782 0.745314 0.052 Uiso 1 1 calc R U . . .
H16C H 0.681339 0.749884 0.708616 0.052 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 C6 1.7587(17) . ?
S1 C4 1.8265(18) . ?
S2 C12 1.7537(17) . ?
S2 C10 1.8331(18) . ?
O1 C13 1.256(2) . ?
O2 C13 1.255(2) . ?
O3 C15 1.250(2) . ?
O4 C15 1.226(2) . ?
N4 C12 1.311(2) . ?
N4 H4C 0.88 . ?
N4 H4D 0.88 . ?
N2 C6 1.308(2) . ?
N2 H2A 0.88 . ?
N2 H2B 0.88 . ?
N1 C6 1.312(2) . ?
N1 H1A 0.88 . ?
N1 H1B 0.88 . ?
N3 C12 1.310(2) . ?
N3 H3A 0.88 . ?
N3 H3B 0.88 . ?
C13 C14 1.511(2) . ?
C15 C16 1.541(3) . ?
C1 C3 1.391(2) 3_567 ?
C1 C2 1.400(2) . ?
C1 C4 1.510(2) . ?
C7 C8 1.393(3) . ?
C7 C9 1.397(3) 3_676 ?
C7 C10 1.508(2) . ?
C3 C2 1.390(2) . ?
C3 H3 0.95 . ?
C2 C5 1.508(2) . ?
C8 C9 1.387(3) . ?
C8 H8 0.95 . ?
C9 C11 1.510(3) . ?
C4 H4A 0.99 . ?
C4 H4B 0.99 . ?
C10 H10A 0.99 . ?
C10 H10B 0.99 . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
C5 H5A 0.98 . ?
C5 H5B 0.98 . ?
C5 H5C 0.98 . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
C16 H16A 0.98 . ?
C16 H16B 0.98 . ?
C16 H16C 0.98 . ?

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
C6 S1 C4 102.90(8) . . ?
C12 S2 C10 102.62(8) . . ?
C12 N4 H4C 120 . . ?
C12 N4 H4D 120 . . ?
H4C N4 H4D 120 . . ?
C6 N2 H2A 120 . . ?
C6 N2 H2B 120 . . ?
H2A N2 H2B 120 . . ?
C6 N1 H1A 120 . . ?
C6 N1 H1B 120 . . ?
H1A N1 H1B 120 . . ?
C12 N3 H3A 120 . . ?
C12 N3 H3B 120 . . ?
H3A N3 H3B 120 . . ?
O2 C13 O1 124.68(15) . . ?
O2 C13 C14 117.65(15) . . ?
O1 C13 C14 117.67(15) . . ?
O4 C15 O3 125.93(18) . . ?
O4 C15 C16 117.92(16) . . ?
O3 C15 C16 116.12(15) . . ?
C3 C1 C2 119.78(16) 3_567 . ?
C3 C1 C4 118.48(15) 3_567 . ?
C2 C1 C4 121.71(16) . . ?
N2 C6 N1 121.40(15) . . ?
N2 C6 S1 123.17(13) . . ?
N1 C6 S1 115.43(13) . . ?
C8 C7 C9 119.92(16) . 3_676 ?
C8 C7 C10 119.07(16) . . ?
C9 C7 C10 120.94(16) 3_676 . ?
N3 C12 N4 122.39(16) . . ?
N3 C12 S2 116.03(13) . . ?
N4 C12 S2 121.56(13) . . ?
C2 C3 C1 122.47(16) . 3_567 ?
C2 C3 H3 118.8 . . ?
C1 C3 H3 118.8 3_567 . ?
C3 C2 C1 117.76(16) . . ?
C3 C2 C5 119.80(16) . . ?
C1 C2 C5 122.44(16) . . ?
C9 C8 C7 122.47(17) . . ?
C9 C8 H8 118.8 . . ?
C7 C8 H8 118.8 . . ?
C8 C9 C7 117.61(17) . 3_676 ?
C8 C9 C11 120.51(17) . . ?
C7 C9 C11 121.88(17) 3_676 . ?
C1 C4 S1 108.80(12) . . ?
C1 C4 H4A 109.9 . . ?
S1 C4 H4A 109.9 . . ?
C1 C4 H4B 109.9 . . ?
S1 C4 H4B 109.9 . . ?
H4A C4 H4B 108.3 . . ?
C7 C10 S2 105.18(12) . . ?
C7 C10 H10A 110.7 . . ?
S2 C10 H10A 110.7 . . ?
C7 C10 H10B 110.7 . . ?
S2 C10 H10B 110.7 . . ?
H10A C10 H10B 108.8 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
C4 S1 C6 N2 6.43(17) . . . . ?
C4 S1 C6 N1 -173.98(14) . . . . ?
C10 S2 C12 N3 -156.11(14) . . . . ?
C10 S2 C12 N4 22.60(17) . . . . ?
C1 C3 C2 C1 -0.2(3) 3_567 . . . ?
C1 C3 C2 C5 -179.44(18) 3_567 . . . ?
C3 C1 C2 C3 0.2(3) 3_567 . . . ?
C4 C1 C2 C3 -177.53(16) . . . . ?
C3 C1 C2 C5 179.41(18) 3_567 . . . ?
C4 C1 C2 C5 1.7(3) . . . . ?
C9 C7 C8 C9 0.1(3) 3_676 . . . ?
C10 C7 C8 C9 177.05(16) . . . . ?
C7 C8 C9 C7 -0.1(3) . . . 3_676 ?
C7 C8 C9 C11 -179.22(17) . . . . ?
C3 C1 C4 S1 101.54(16) 3_567 . . . ?
C2 C1 C4 S1 -80.71(18) . . . . ?
C6 S1 C4 C1 -179.22(12) . . . . ?
C8 C7 C10 S2 -92.89(17) . . . . ?
C9 C7 C10 S2 84.04(18) 3_676 . . . ?
C12 S2 C10 C7 165.60(12) . . . . ?

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
_geom_hbond_publ_flag
N4 H4C O3 0.88 1.9 2.7766(19) 178.7 1_565 yes
N4 H4D O1 0.88 2.09 2.8551(19) 144.6 3_676 yes
N2 H2A O2 0.88 1.91 2.7904(19) 173.8 . yes
N2 H2B O3 0.88 1.91 2.7366(19) 155.1 1_455 yes
N1 H1A O1 0.88 1.88 2.7567(19) 173.4 . yes
N1 H1B O4 0.88 1.9 2.695(2) 149.7 . yes
N3 H3A O4 0.88 1.97 2.850(2) 174.8 1_565 yes
N3 H3B O2 0.88 1.95 2.8256(19) 173.9 3_576 yes

####################################################################### 
# 
# 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_eg_8
_database_code_depnum_ccdc_archive 'CCDC 1944696'
loop_
_audit_author_name
_audit_author_address
'Anna Dolega'
;Gdansk University of Technology
Poland
;
_audit_update_record             
;
2020-06-29 deposited with the CCDC.	2020-07-22 downloaded from the CCDC.
;

_audit_creation_date             2020-06-25T10:32:20-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C20 H27 Cl N4 O8 S2 U'
_chemical_formula_weight         789.05

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   12.442(6)
_cell_length_b                   7.5206(15)
_cell_length_c                   29.720(10)
_cell_angle_alpha                90
_cell_angle_beta                 96.79(3)
_cell_angle_gamma                90
_cell_volume                     2761.5(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    8809
_cell_measurement_theta_min      2.49
_cell_measurement_theta_max      29.52

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.514
_exptl_crystal_size_mid          0.362
_exptl_crystal_size_min          0.282
_exptl_crystal_density_diffrn    1.898
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1520
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 -1 -4 0.116
-3 0 -5 0.141
3 4 0 0.303
1 0 2 0.136
1 -1 3 0.172
1 0 -3 0.155
1 -1 -2 0.148
0 -1 1 0.211
-2 1 5 0.222
2 0 3 0.141
-2 1 -5 0.168
-3 -2 -2 0.159
-1 0 3 0.135


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    6.175
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
        Structure Analysis", published in
        F. R. Ahmed (Editor), "Crystallographic Computing",
        Munksgaard, Copenhagen (1970), 255 - 270
;
_exptl_absorpt_correction_T_min  0.1567
_exptl_absorpt_correction_T_max  0.282

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_reflns_av_R_equivalents  0.075
_diffrn_reflns_av_unetI/netI     0.0365
_diffrn_reflns_number            28024
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.489
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_reflns_Friedel_coverage         0
_reflns_number_total             5414
_reflns_number_gt                5161
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_cell_refinement       
;
        X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        
;
        X-Area Integrate 1.72.0.0 (STOE, 2018)
        X-Area X-Red32 1.63.4.0 (STOE, 2017)
;
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image
processing, for the correction and scaling of reflection intensities and
        for outlier rejection, version 1.81, Darmstadt 2018
;

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_shelx_SHELXL_version_number     2018/3
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0417P)²+30.1062P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5414
_refine_ls_number_parameters     300
_refine_ls_number_restraints     8
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1185
_refine_ls_wR_factor_gt          0.1172
_refine_ls_goodness_of_fit_ref   1.175
_refine_ls_restrained_S_all      1.175
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         2.045
_refine_diff_density_min         -1.644
_refine_diff_density_rms         0.187

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 '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 0.006 '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'
U U -9.6767 9.6646 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
U1 U 0.74704(2) 0.19334(3) 0.96024(2) 0.02038(10) Uani 1 1 d . . . . .
S2 S 1.05684(16) 0.9558(2) 0.90204(7) 0.0280(4) Uani 1 1 d . . . . .
Cl1 Cl 1.88467(18) 1.7757(3) 0.77911(7) 0.0370(5) Uani 1 1 d . . . . .
S1 S 1.50864(19) 1.5527(3) 0.85168(8) 0.0402(5) Uani 1 1 d . . . . .
O7 O 0.7631(5) 0.0931(8) 0.88237(18) 0.0335(13) Uani 1 1 d . . . . .
O5 O 0.6554(5) -0.0009(7) 1.00958(17) 0.0271(11) Uani 1 1 d . . . . .
O2 O 0.6239(4) 0.2975(7) 0.94112(18) 0.0254(11) Uani 1 1 d . . . . .
O1 O 0.8731(4) 0.0911(7) 0.97869(18) 0.0284(11) Uani 1 1 d . . . . .
O8 O 0.8323(5) 0.3544(7) 0.89996(18) 0.0299(12) Uani 1 1 d . . . . .
C19 C 0.8099(6) 0.2318(10) 0.8711(2) 0.0247(15) Uani 1 1 d . . . . .
C20 C 0.8358(8) 0.2507(13) 0.8235(3) 0.039(2) Uani 1 1 d . . . . .
H20A H 0.879988 0.149581 0.815883 0.058 Uiso 1 1 calc R U . . .
H20B H 0.87589 0.3614 0.820536 0.058 Uiso 1 1 calc R U . . .
H20C H 0.768415 0.253375 0.802725 0.058 Uiso 1 1 calc R U . . .
O6 O 0.6589(5) -0.0928(7) 0.94075(18) 0.0311(12) Uani 1 1 d . . . . .
C18 C 0.5642(7) -0.2762(10) 0.9885(3) 0.0299(17) Uani 1 1 d . . . . .
H18A H 0.572565 -0.301206 1.021096 0.045 Uiso 1 1 calc R U . . .
H18B H 0.58919 -0.378709 0.972248 0.045 Uiso 1 1 calc R U . . .
H18C H 0.487816 -0.253306 0.978026 0.045 Uiso 1 1 calc R U . . .
C17 C 0.6296(6) -0.1172(10) 0.9796(3) 0.0266(16) Uani 1 1 d . . . . .
O4 O 0.7449(5) 0.3332(7) 1.03558(18) 0.0311(13) Uani 1 1 d . . . . .
O3 O 0.8234(5) 0.4830(7) 0.98576(17) 0.0276(12) Uani 1 1 d . . . . .
C15 C 0.7952(7) 0.4708(10) 1.0256(3) 0.0300(17) Uani 1 1 d . . . . .
C16 C 0.8244(8) 0.6153(11) 1.0599(3) 0.039(2) Uani 1 1 d . . . . .
H16A H 0.790349 0.590573 1.087336 0.059 Uiso 1 1 calc R U . . .
H16B H 0.79871 0.730087 1.047239 0.059 Uiso 1 1 calc R U . . .
H16C H 0.903187 0.619342 1.067501 0.059 Uiso 1 1 calc R U . . .
C8 C 1.1063(9) 1.1846(15) 0.8022(4) 0.0503(8) Uani 1 1 d . . . . .
H8 H 1.048637 1.104129 0.805152 0.06 Uiso 1 1 calc R U . . .
C7 C 1.2115(9) 1.1474(15) 0.8263(4) 0.0503(8) Uani 1 1 d . . . . .
C6 C 1.2299(9) 0.9960(15) 0.8550(4) 0.0503(8) Uani 1 1 d . . . . .
C13 C 1.1392(8) 0.8687(13) 0.8601(3) 0.0408(15) Uani 1 1 d . . . . .
H13A H 1.16903 0.751116 0.869941 0.049 Uiso 1 1 calc R U . . .
H13B H 1.093946 0.853554 0.830607 0.049 Uiso 1 1 calc R U . . .
C3 C 1.4042(9) 1.2237(15) 0.8392(4) 0.0503(8) Uani 1 1 d . . . . .
C12 C 1.2985(9) 1.2610(16) 0.8188(4) 0.0503(8) Uani 1 1 d . . . . .
C11 C 1.2706(9) 1.4129(15) 0.7886(3) 0.0503(8) Uani 1 1 d . . . . .
H11 H 1.32673 1.492177 0.782725 0.06 Uiso 1 1 calc R U . . .
C5 C 1.3289(9) 0.9696(15) 0.8772(4) 0.0503(8) Uani 1 1 d . . . . .
H5 H 1.341254 0.874864 0.898285 0.06 Uiso 1 1 calc R U . . .
C4 C 1.4189(9) 1.0889(15) 0.8685(3) 0.0503(8) Uani 1 1 d . . . . .
H4 H 1.488935 1.069036 0.884203 0.06 Uiso 1 1 calc R U . . .
C10 C 1.1697(8) 1.4454(16) 0.7690(3) 0.0503(8) Uani 1 1 d . . . . .
H10 H 1.155806 1.547962 0.75054 0.06 Uiso 1 1 calc R U . . .
C9 C 1.0864(9) 1.3316(15) 0.7752(4) 0.0503(8) Uani 1 1 d . . . . .
H9 H 1.015342 1.354711 0.760963 0.06 Uiso 1 1 calc R U . . .
N3 N 0.9464(6) 0.6570(10) 0.8802(2) 0.0337(16) Uani 1 1 d D . . . .
H3A H 0.905(6) 0.574(10) 0.888(3) 0.02(2) Uiso 1 1 d D . . . .
H3B H 0.950(8) 0.693(12) 0.853(3) 0.03(3) Uiso 1 1 d D . . . .
N4 N 0.9614(6) 0.7418(9) 0.9542(2) 0.0266(14) Uani 1 1 d D . . . .
H4A H 0.914(6) 0.677(10) 0.961(3) 0.02(2) Uiso 1 1 d D . . . .
H4B H 0.987(7) 0.809(11) 0.971(3) 0.03(2) Uiso 1 1 d D . . . .
C14 C 0.9803(6) 0.7672(10) 0.9123(3) 0.0245(15) Uani 1 1 d . . . . .
C2 C 1.4998(8) 1.3321(12) 0.8256(3) 0.0408(15) Uani 1 1 d . . . . .
H2A H 1.491858 1.345249 0.79223 0.049 Uiso 1 1 calc R U . . .
H2B H 1.567888 1.266608 0.834786 0.049 Uiso 1 1 calc R U . . .
N2 N 1.6568(6) 1.5938(11) 0.7920(3) 0.0375(17) Uani 1 1 d D . . . .
H2C H 1.720(5) 1.640(10) 0.790(2) 0.010(17) Uiso 1 1 d D . . . .
H2D H 1.626(7) 1.521(11) 0.775(3) 0.03(2) Uiso 1 1 d D . . . .
N1 N 1.6677(7) 1.7748(11) 0.8534(3) 0.0394(18) Uani 1 1 d D . . . .
H1A H 1.712(7) 1.825(12) 0.840(3) 0.03(2) Uiso 1 1 d D . . . .
H1B H 1.646(8) 1.808(13) 0.876(3) 0.04(3) Uiso 1 1 d D . . . .
C1 C 1.6211(7) 1.6439(11) 0.8294(3) 0.0297(17) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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
U1 O2 1.755(5) . ?
U1 O1 1.774(6) . ?
U1 O5 2.445(5) . ?
U1 O6 2.453(5) . ?
U1 O3 2.460(5) . ?
U1 O7 2.464(5) . ?
U1 O4 2.476(5) . ?
U1 O8 2.500(5) . ?
U1 C17 2.850(8) . ?
U1 C19 2.864(7) . ?
U1 C15 2.865(8) . ?
S2 C14 1.755(8) . ?
S2 C13 1.827(9) . ?
S1 C1 1.756(9) . ?
S1 C2 1.829(9) . ?
O7 C19 1.259(10) . ?
O5 C17 1.262(9) . ?
O8 C19 1.268(9) . ?
C19 C20 1.496(10) . ?
O6 C17 1.266(9) . ?
C18 C17 1.487(10) . ?
O4 C15 1.263(10) . ?
O3 C15 1.276(10) . ?
C15 C16 1.506(11) . ?
C8 C9 1.371(15) . ?
C8 C7 1.444(15) . ?
C7 C12 1.417(15) . ?
C7 C6 1.424(15) . ?
C6 C5 1.342(15) . ?
C6 C13 1.501(14) . ?
C3 C4 1.335(15) . ?
C3 C12 1.410(15) . ?
C3 C2 1.535(14) . ?
C12 C11 1.469(15) . ?
C11 C10 1.343(15) . ?
C5 C4 1.481(14) . ?
C10 C9 1.374(15) . ?
N3 C14 1.295(11) . ?
N4 C14 1.309(10) . ?
N2 C1 1.301(11) . ?
N1 C1 1.309(11) . ?

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
O2 U1 O1 178.7(2) . . ?
O2 U1 O5 90.6(2) . . ?
O1 U1 O5 90.8(2) . . ?
O2 U1 O6 88.1(2) . . ?
O1 U1 O6 92.7(2) . . ?
O5 U1 O6 52.45(17) . . ?
O2 U1 O3 89.7(2) . . ?
O1 U1 O3 89.6(2) . . ?
O5 U1 O3 122.31(17) . . ?
O6 U1 O3 174.27(17) . . ?
O2 U1 O7 89.8(2) . . ?
O1 U1 O7 89.5(2) . . ?
O5 U1 O7 118.41(18) . . ?
O6 U1 O7 66.02(18) . . ?
O3 U1 O7 119.28(18) . . ?
O2 U1 O4 90.1(2) . . ?
O1 U1 O4 90.5(2) . . ?
O5 U1 O4 69.87(18) . . ?
O6 U1 O4 122.25(18) . . ?
O3 U1 O4 52.44(18) . . ?
O7 U1 O4 171.71(19) . . ?
O2 U1 O8 88.8(2) . . ?
O1 U1 O8 89.8(2) . . ?
O5 U1 O8 170.57(17) . . ?
O6 U1 O8 118.12(17) . . ?
O3 U1 O8 67.10(17) . . ?
O7 U1 O8 52.18(18) . . ?
O4 U1 O8 119.53(18) . . ?
O2 U1 C17 89.0(2) . . ?
O1 U1 C17 92.2(2) . . ?
O5 U1 C17 26.2(2) . . ?
O6 U1 C17 26.3(2) . . ?
O3 U1 C17 148.4(2) . . ?
O7 U1 C17 92.3(2) . . ?
O4 U1 C17 96.0(2) . . ?
O8 U1 C17 144.4(2) . . ?
O2 U1 C19 88.8(2) . . ?
O1 U1 C19 90.1(2) . . ?
O5 U1 C19 144.4(2) . . ?
O6 U1 C19 91.9(2) . . ?
O3 U1 C19 93.3(2) . . ?
O7 U1 C19 26.0(2) . . ?
O4 U1 C19 145.8(2) . . ?
O8 U1 C19 26.2(2) . . ?
C17 U1 C19 118.2(2) . . ?
O2 U1 C15 89.9(2) . . ?
O1 U1 C15 90.0(2) . . ?
O5 U1 C15 96.0(2) . . ?
O6 U1 C15 148.3(2) . . ?
O3 U1 C15 26.4(2) . . ?
O7 U1 C15 145.6(2) . . ?
O4 U1 C15 26.1(2) . . ?
O8 U1 C15 93.4(2) . . ?
C17 U1 C15 122.1(2) . . ?
C19 U1 C15 119.7(2) . . ?
C14 S2 C13 100.8(4) . . ?
C1 S1 C2 101.9(4) . . ?
C19 O7 U1 95.0(4) . . ?
C17 O5 U1 95.1(4) . . ?
C19 O8 U1 93.1(4) . . ?
O7 C19 O8 119.6(7) . . ?
O7 C19 C20 119.2(7) . . ?
O8 C19 C20 121.1(7) . . ?
O7 C19 U1 59.0(4) . . ?
O8 C19 U1 60.6(4) . . ?
C20 C19 U1 176.6(6) . . ?
C17 O6 U1 94.6(5) . . ?
O5 C17 O6 117.8(7) . . ?
O5 C17 C18 122.1(7) . . ?
O6 C17 C18 120.1(7) . . ?
O5 C17 U1 58.7(4) . . ?
O6 C17 U1 59.1(4) . . ?
C18 C17 U1 177.5(6) . . ?
C15 O4 U1 94.4(4) . . ?
C15 O3 U1 94.8(5) . . ?
O4 C15 O3 118.4(7) . . ?
O4 C15 C16 121.2(7) . . ?
O3 C15 C16 120.4(8) . . ?
O4 C15 U1 59.5(4) . . ?
O3 C15 U1 58.8(4) . . ?
C16 C15 U1 178.1(6) . . ?
C9 C8 C7 122.5(10) . . ?
C12 C7 C6 120.3(10) . . ?
C12 C7 C8 118.0(10) . . ?
C6 C7 C8 121.6(10) . . ?
C5 C6 C7 119.0(10) . . ?
C5 C6 C13 120.9(10) . . ?
C7 C6 C13 120.1(10) . . ?
C6 C13 S2 109.2(7) . . ?
C4 C3 C12 118.7(10) . . ?
C4 C3 C2 121.6(10) . . ?
C12 C3 C2 119.6(10) . . ?
C3 C12 C7 120.2(10) . . ?
C3 C12 C11 123.9(10) . . ?
C7 C12 C11 115.8(10) . . ?
C10 C11 C12 123.2(10) . . ?
C6 C5 C4 119.6(10) . . ?
C3 C4 C5 121.7(10) . . ?
C11 C10 C9 120.6(11) . . ?
C8 C9 C10 119.6(11) . . ?
N3 C14 N4 121.8(7) . . ?
N3 C14 S2 121.8(6) . . ?
N4 C14 S2 116.4(6) . . ?
C3 C2 S1 112.3(7) . . ?
N2 C1 N1 120.6(8) . . ?
N2 C1 S1 125.2(7) . . ?
N1 C1 S1 114.2(7) . . ?

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
_geom_hbond_publ_flag
N3 H3A O8 0.86(7) 1.94(7) 2.782(9) 168(8) . yes
N3 H3B Cl1 0.87(7) 2.33(8) 3.142(7) 157(9) 1_445 yes
N4 H4A O3 0.82(7) 2.03(7) 2.828(9) 167(8) . yes
N4 H4B O1 0.76(7) 2.57(9) 2.972(9) 115(8) 1_565 yes
N4 H4B O1 0.76(7) 2.28(8) 2.972(9) 152(9) 3_767 yes
N2 H2C Cl1 0.87(6) 2.34(7) 3.212(8) 176(7) . yes
N2 H2D Cl1 0.80(7) 2.45(8) 3.193(8) 155(8) 2_846 yes
N1 H1A Cl1 0.81(7) 2.99(8) 3.684(9) 145(8) . yes
N1 H1B O6 0.79(7) 2.06(8) 2.795(9) 156(10) 1_675 yes

