# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_ZR2_4731BZA_SU_101_3
_database_code_depnum_ccdc_archive 'CCDC 1540877'
_audit_update_record             
;
2017-10-27 deposited with the CCDC.
2017-12-11 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT420_ZR2_4731BZA_SU_101_3 
;
PROBLEM: D-H Without Acceptor      *O109   -- *H109   ...     Please Check
RESPONSE: The coformer molecule including O109 and H109 has no acceptor because this molecule is disordered on the inversion center.
;
# Added during the CSD deposition process: Friday 27 October 2017 05:30 AM
# end Validation Reply Form


#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C21.5 H17 F3 N5 O4 S2'
_chemical_formula_moiety         'C21.5 H17 F3 N5 O4 S2'
_chemical_formula_weight         530.52
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   11.4209(2)
_cell_length_b                   20.5581(4)
_cell_length_c                   9.97928(18)
_cell_angle_alpha                90.0000
_cell_angle_beta                 91.5970(11)
_cell_angle_gamma                90.0000
_cell_volume                     2342.14(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    19085
_cell_measurement_theta_min      3.87
_cell_measurement_theta_max      68.16
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.504
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1088.00
_exptl_absorpt_coefficient_mu    2.640
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.715
_exptl_absorpt_correction_T_max  0.924

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            4275
_diffrn_reflns_av_R_equivalents  0.0734
_diffrn_reflns_theta_max         68.180
_diffrn_reflns_theta_min         3.872
_diffrn_reflns_theta_full        68.180
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       12
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4275
_reflns_number_gt                2450
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0929
_refine_ls_R_factor_gt           0.0627
_refine_ls_wR_factor_ref         0.1669
_refine_ls_wR_factor_gt          0.1493
_refine_ls_number_restraints     259
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         4275
_refine_ls_number_parameters     420
_refine_ls_goodness_of_fit_ref   0.892
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0119P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.41
_refine_diff_density_min         -0.53
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.1713(4) 0.2561(2) -0.1668(5) 0.0460(12) Uani 1 1 d D . .
H1A H 0.177(5) 0.267(3) -0.0768(19) 0.055 Uiso 1 1 d D . .
H1B H 0.102(3) 0.235(2) -0.187(6) 0.055 Uiso 1 1 d D . .
S2 S 0.28208(12) 0.22744(6) -0.24141(13) 0.0395(4) Uani 1 1 d . . .
O3 O 0.2479(3) 0.21746(17) -0.3797(4) 0.0490(10) Uani 1 1 d . . .
O4 O 0.3791(3) 0.26922(16) -0.2096(4) 0.0452(9) Uani 1 1 d . . .
C5 C 0.3153(4) 0.1504(2) -0.1731(5) 0.0351(11) Uani 1 1 d . . .
C6 C 0.2967(5) 0.0941(2) -0.2496(5) 0.0424(13) Uani 1 1 d . . .
H6 H 0.2676 0.0984 -0.3393 0.051 Uiso 1 1 calc R . .
N7 N 0.3183(4) 0.0344(2) -0.2009(4) 0.0431(11) Uani 1 1 d . . .
C8 C 0.3568(4) 0.0300(2) -0.0736(5) 0.0376(12) Uani 1 1 d . . .
H8 H 0.3709 -0.0121 -0.0373 0.045 Uiso 1 1 calc R . .
C9 C 0.3774(4) 0.0834(2) 0.0084(5) 0.0334(11) Uani 1 1 d . . .
C10 C 0.3563(4) 0.1452(2) -0.0416(5) 0.0350(11) Uani 1 1 d . . .
H10 H 0.3695 0.1828 0.0122 0.042 Uiso 1 1 calc R . .
N11 N 0.4184(3) 0.07468(18) 0.1440(4) 0.0319(9) Uani 1 1 d . A .
C12 C 0.5143(4) 0.1060(2) 0.1957(5) 0.0318(11) Uani 1 1 d . A .
S13 S 0.61520(11) 0.14504(6) 0.11250(14) 0.0399(4) Uani 1 1 d . . .
N14 N 0.5140(3) 0.09668(18) 0.3340(4) 0.0350(10) Uani 1 1 d . . .
C15 C 0.4160(4) 0.0622(2) 0.3732(5) 0.0352(12) Uani 1 1 d . A .
O16 O 0.3925(3) 0.04876(17) 0.4874(4) 0.0446(9) Uani 1 1 d . . .
C17 C 0.3469(4) 0.0434(2) 0.2473(5) 0.0325(11) Uani 1 1 d . . .
C18 C 0.3448(5) -0.0309(2) 0.2361(5) 0.0420(13) Uani 1 1 d . A .
H18A H 0.2966 -0.0490 0.3068 0.063 Uiso 1 1 calc R . .
H18B H 0.4248 -0.0478 0.2462 0.063 Uiso 1 1 calc R . .
H18C H 0.3117 -0.0435 0.1483 0.063 Uiso 1 1 calc R . .
C19 C 0.2242(4) 0.0721(3) 0.2514(6) 0.0421(13) Uani 1 1 d . A .
H19A H 0.1800 0.0501 0.3209 0.063 Uiso 1 1 calc R . .
H19B H 0.1842 0.0660 0.1641 0.063 Uiso 1 1 calc R . .
H19C H 0.2294 0.1187 0.2717 0.063 Uiso 1 1 calc R . .
C20A C 0.6045(10) 0.1258(7) 0.4121(12) 0.031(3) Uani 0.569(10) 1 d PDU A 1
C21A C 0.7185(9) 0.1042(6) 0.4017(10) 0.034(2) Uani 0.569(10) 1 d PDU A 1
H21A H 0.7380 0.0725 0.3366 0.041 Uiso 0.569(10) 1 calc PR A 1
C22A C 0.8037(8) 0.1296(5) 0.4881(11) 0.038(2) Uani 0.569(10) 1 d PDU A 1
C23A C 0.9275(10) 0.1058(5) 0.4820(12) 0.066(3) Uani 0.569(10) 1 d PDU A 1
F24A F 0.9426(7) 0.0619(5) 0.3884(10) 0.109(3) Uani 0.569(10) 1 d PDU A 1
F25A F 0.9615(15) 0.0757(7) 0.5957(13) 0.104(4) Uani 0.569(10) 1 d PDU A 1
F26A F 1.0033(6) 0.1540(4) 0.4658(11) 0.092(3) Uani 0.569(10) 1 d PDU A 1
C27A C 0.7731(11) 0.1707(6) 0.5943(13) 0.049(3) Uani 0.569(10) 1 d PDU A 1
C28A C 0.6587(11) 0.1905(7) 0.6040(14) 0.052(3) Uani 0.569(10) 1 d PDU A 1
H28A H 0.6382 0.2213 0.6702 0.062 Uiso 0.569(10) 1 calc PR A 1
C29A C 0.5735(12) 0.1654(10) 0.5177(18) 0.047(4) Uani 0.569(10) 1 d PDU A 1
H29A H 0.4934 0.1753 0.5308 0.057 Uiso 0.569(10) 1 calc PR A 1
C30A C 0.8622(11) 0.2035(5) 0.6751(14) 0.060(3) Uani 0.569(10) 1 d PDU A 1
N31A N 0.9301(10) 0.2285(5) 0.7422(13) 0.077(4) Uani 0.569(10) 1 d PDU A 1
C20B C 0.5914(15) 0.1211(11) 0.4439(17) 0.042(4) Uani 0.431(10) 1 d PDU A 2
C21B C 0.7098(14) 0.1094(10) 0.4395(16) 0.042(3) Uani 0.431(10) 1 d PDU A 2
H21B H 0.7403 0.0815 0.3729 0.051 Uiso 0.431(10) 1 calc PR A 2
C22B C 0.7841(11) 0.1388(9) 0.5338(15) 0.045(3) Uani 0.431(10) 1 d PDU A 2
C23B C 0.9119(12) 0.1260(7) 0.5281(15) 0.072(3) Uani 0.431(10) 1 d PDU A 2
F24B F 0.9448(11) 0.1020(8) 0.4121(13) 0.110(4) Uani 0.431(10) 1 d PDU A 2
F25B F 0.9481(19) 0.0826(8) 0.6200(16) 0.099(4) Uani 0.431(10) 1 d PDU A 2
F26B F 0.9772(9) 0.1787(6) 0.5524(15) 0.101(4) Uani 0.431(10) 1 d PDU A 2
C27B C 0.7394(14) 0.1835(8) 0.6241(19) 0.057(3) Uani 0.431(10) 1 d PDU A 2
C28B C 0.6200(13) 0.1910(7) 0.6323(16) 0.039(3) Uani 0.431(10) 1 d PDU A 2
H28B H 0.5885 0.2136 0.7061 0.047 Uiso 0.431(10) 1 calc PR A 2
C29B C 0.5454(14) 0.1657(12) 0.533(2) 0.034(3) Uani 0.431(10) 1 d PDU A 2
H29B H 0.4655 0.1784 0.5268 0.041 Uiso 0.431(10) 1 calc PR A 2
C30B C 0.8082(15) 0.2053(7) 0.7405(19) 0.064(4) Uani 0.431(10) 1 d PDU A 2
N31B N 0.8592(14) 0.2235(7) 0.8335(17) 0.083(4) Uani 0.431(10) 1 d PDU A 2
C101 C 0.0691(7) -0.0239(4) -0.1180(8) 0.066(4) Uiso 0.50 1 d PGDU B -1
H101 H 0.1029 -0.0018 -0.1911 0.079 Uiso 0.50 1 calc PR B -1
C102 C 0.0809(8) -0.0909(4) -0.1060(10) 0.077(4) Uiso 0.50 1 d PGDU B -1
H102 H 0.1228 -0.1147 -0.1708 0.092 Uiso 0.50 1 calc PR B -1
C103 C 0.0314(10) -0.1232(3) 0.0010(12) 0.126(9) Uiso 0.50 1 d PGDU B -1
H103 H 0.0395 -0.1691 0.0092 0.151 Uiso 0.50 1 calc PR B -1
C104 C -0.0298(10) -0.0885(5) 0.0958(10) 0.086(5) Uiso 0.50 1 d PGDU B -1
H104 H -0.0636 -0.1106 0.1689 0.103 Uiso 0.50 1 calc PR B -1
C105 C -0.0416(9) -0.0214(5) 0.0837(9) 0.062(3) Uiso 0.50 1 d PGDU B -1
H105 H -0.0834 0.0023 0.1485 0.075 Uiso 0.50 1 calc PR B -1
C106 C 0.0079(8) 0.0109(3) -0.0232(9) 0.074(4) Uiso 0.50 1 d PGDU B -1
C107 C -0.0029(11) 0.0820(5) -0.0429(13) 0.072(4) Uiso 0.50 1 d PDU B -1
O108 O 0.0583(11) 0.1171(6) -0.1138(13) 0.115(4) Uiso 0.50 1 d PDU B -1
O109 O -0.0850(11) 0.1109(7) 0.0263(13) 0.110(4) Uiso 0.50 1 d PDU B -1
H109 H -0.0842 0.1511 0.0107 0.132 Uiso 0.50 1 calc PRD B -1


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.2 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.2'

#==============================================================================
# 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
N1 S2 1.599(5) . ?
N1 H1A 0.924(13) . ?
N1 H1B 0.924(13) . ?
S2 O4 1.430(3) . ?
S2 O3 1.439(4) . ?
S2 C5 1.762(5) . ?
C5 C10 1.385(7) . ?
C5 C6 1.398(7) . ?
C6 N7 1.341(6) . ?
C6 H6 0.9500 . ?
N7 C8 1.336(6) . ?
C8 C9 1.385(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.385(6) . ?
C9 N11 1.430(6) . ?
C10 H10 0.9500 . ?
N11 C12 1.360(6) . ?
N11 C17 1.480(6) . ?
C12 N14 1.393(6) . ?
C12 S13 1.648(5) . ?
N14 C15 1.390(6) . ?
N14 C20A 1.410(11) . ?
N14 C20B 1.477(17) . ?
C15 O16 1.210(6) . ?
C15 C17 1.515(7) . ?
C17 C19 1.522(6) . ?
C17 C18 1.532(6) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20A C21A 1.383(12) . ?
C20A C29A 1.385(13) . ?
C21A C22A 1.384(11) . ?
C21A H21A 0.9500 . ?
C22A C27A 1.408(14) . ?
C22A C23A 1.499(13) . ?
C23A F24A 1.314(10) . ?
C23A F26A 1.329(9) . ?
C23A F25A 1.340(9) . ?
C27A C28A 1.373(14) . ?
C27A C30A 1.447(11) . ?
C28A C29A 1.381(13) . ?
C28A H28A 0.9500 . ?
C29A H29A 0.9500 . ?
C30A N31A 1.134(11) . ?
C20B C21B 1.376(16) . ?
C20B C29B 1.392(15) . ?
C21B C22B 1.389(16) . ?
C21B H21B 0.9500 . ?
C22B C27B 1.393(16) . ?
C22B C23B 1.486(15) . ?
C23B F24B 1.322(10) . ?
C23B F26B 1.332(10) . ?
C23B F25B 1.338(10) . ?
C27B C28B 1.378(17) . ?
C27B C30B 1.455(15) . ?
C28B C29B 1.387(14) . ?
C28B H28B 0.9500 . ?
C29B H29B 0.9500 . ?
C30B N31B 1.145(14) . ?
C101 C102 1.3900 . ?
C101 C106 1.3900 . ?
C101 H101 0.9500 . ?
C102 C103 1.3900 . ?
C102 H102 0.9500 . ?
C103 C104 1.3900 . ?
C103 H103 0.9500 . ?
C104 C105 1.3900 . ?
C104 H104 0.9500 . ?
C105 C106 1.3900 . ?
C105 H105 0.9500 . ?
C106 C107 1.481(9) . ?
C107 O108 1.239(11) . ?
C107 O109 1.321(10) . ?
O109 H109 0.8400 . ?

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
S2 N1 H1A 120(3) . . ?
S2 N1 H1B 114(4) . . ?
H1A N1 H1B 111(5) . . ?
O4 S2 O3 119.1(2) . . ?
O4 S2 N1 107.1(2) . . ?
O3 S2 N1 107.6(2) . . ?
O4 S2 C5 107.3(2) . . ?
O3 S2 C5 107.0(2) . . ?
N1 S2 C5 108.4(3) . . ?
C10 C5 C6 119.8(5) . . ?
C10 C5 S2 119.9(4) . . ?
C6 C5 S2 120.3(4) . . ?
N7 C6 C5 122.3(5) . . ?
N7 C6 H6 118.8 . . ?
C5 C6 H6 118.8 . . ?
C8 N7 C6 117.4(4) . . ?
N7 C8 C9 123.7(5) . . ?
N7 C8 H8 118.2 . . ?
C9 C8 H8 118.2 . . ?
C8 C9 C10 119.3(5) . . ?
C8 C9 N11 120.3(4) . . ?
C10 C9 N11 120.3(4) . . ?
C5 C10 C9 117.5(5) . . ?
C5 C10 H10 121.2 . . ?
C9 C10 H10 121.2 . . ?
C12 N11 C9 122.6(4) . . ?
C12 N11 C17 113.3(4) . . ?
C9 N11 C17 122.8(4) . . ?
N11 C12 N14 106.7(4) . . ?
N11 C12 S13 127.3(4) . . ?
N14 C12 S13 125.9(4) . . ?
C15 N14 C12 111.9(4) . . ?
C15 N14 C20A 130.1(7) . . ?
C12 N14 C20A 117.9(6) . . ?
C15 N14 C20B 115.7(8) . . ?
C12 N14 C20B 132.2(9) . . ?
C20A N14 C20B 14.4(11) . . ?
O16 C15 N14 125.7(5) . . ?
O16 C15 C17 126.7(5) . . ?
N14 C15 C17 107.5(4) . . ?
N11 C17 C15 100.5(4) . . ?
N11 C17 C19 112.1(4) . . ?
C15 C17 C19 109.7(4) . . ?
N11 C17 C18 113.0(4) . . ?
C15 C17 C18 108.8(4) . . ?
C19 C17 C18 112.1(4) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21A C20A C29A 120.4(10) . . ?
C21A C20A N14 120.0(10) . . ?
C29A C20A N14 118.1(10) . . ?
C20A C21A C22A 118.7(10) . . ?
C20A C21A H21A 120.7 . . ?
C22A C21A H21A 120.7 . . ?
C21A C22A C27A 120.7(9) . . ?
C21A C22A C23A 119.9(10) . . ?
C27A C22A C23A 118.8(8) . . ?
F24A C23A F26A 109.1(10) . . ?
F24A C23A F25A 104.1(10) . . ?
F26A C23A F25A 105.8(10) . . ?
F24A C23A C22A 113.3(8) . . ?
F26A C23A C22A 112.3(9) . . ?
F25A C23A C22A 111.6(11) . . ?
C28A C27A C22A 119.2(9) . . ?
C28A C27A C30A 118.6(11) . . ?
C22A C27A C30A 120.9(11) . . ?
C27A C28A C29A 120.0(11) . . ?
C27A C28A H28A 120.0 . . ?
C29A C28A H28A 120.0 . . ?
C28A C29A C20A 120.2(11) . . ?
C28A C29A H29A 119.9 . . ?
C20A C29A H29A 119.9 . . ?
N31A C30A C27A 177.7(17) . . ?
C21B C20B C29B 121.7(15) . . ?
C21B C20B N14 119.0(12) . . ?
C29B C20B N14 118.1(13) . . ?
C20B C21B C22B 119.0(13) . . ?
C20B C21B H21B 120.5 . . ?
C22B C21B H21B 120.5 . . ?
C21B C22B C27B 119.9(12) . . ?
C21B C22B C23B 118.6(13) . . ?
C27B C22B C23B 121.3(13) . . ?
F24B C23B F26B 106.9(12) . . ?
F24B C23B F25B 105.1(12) . . ?
F26B C23B F25B 104.9(12) . . ?
F24B C23B C22B 113.8(11) . . ?
F26B C23B C22B 113.2(12) . . ?
F25B C23B C22B 112.2(14) . . ?
C28B C27B C22B 119.6(11) . . ?
C28B C27B C30B 115.6(14) . . ?
C22B C27B C30B 121.4(13) . . ?
C27B C28B C29B 120.3(14) . . ?
C27B C28B H28B 119.8 . . ?
C29B C28B H28B 119.8 . . ?
C28B C29B C20B 117.9(14) . . ?
C28B C29B H29B 121.0 . . ?
C20B C29B H29B 121.0 . . ?
N31B C30B C27B 177.8(19) . . ?
C102 C101 C106 120.0 . . ?
C102 C101 H101 120.0 . . ?
C106 C101 H101 120.0 . . ?
C103 C102 C101 120.0 . . ?
C103 C102 H102 120.0 . . ?
C101 C102 H102 120.0 . . ?
C104 C103 C102 120.0 . . ?
C104 C103 H103 120.0 . . ?
C102 C103 H103 120.0 . . ?
C103 C104 C105 120.0 . . ?
C103 C104 H104 120.0 . . ?
C105 C104 H104 120.0 . . ?
C104 C105 C106 120.0 . . ?
C104 C105 H105 120.0 . . ?
C106 C105 H105 120.0 . . ?
C105 C106 C101 120.0 . . ?
C105 C106 C107 122.7(7) . . ?
C101 C106 C107 117.3(7) . . ?
O108 C107 O109 117.2(12) . . ?
O108 C107 C106 127.2(12) . . ?
O109 C107 C106 115.6(11) . . ?

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
O4 S2 C5 C10 48.2(5) . . . . ?
O3 S2 C5 C10 177.0(4) . . . . ?
N1 S2 C5 C10 -67.1(5) . . . . ?
O4 S2 C5 C6 -134.0(4) . . . . ?
O3 S2 C5 C6 -5.1(5) . . . . ?
N1 S2 C5 C6 110.7(5) . . . . ?
C10 C5 C6 N7 -0.7(8) . . . . ?
S2 C5 C6 N7 -178.5(4) . . . . ?
C5 C6 N7 C8 1.3(8) . . . . ?
C6 N7 C8 C9 -1.3(8) . . . . ?
N7 C8 C9 C10 0.8(8) . . . . ?
N7 C8 C9 N11 179.8(5) . . . . ?
C6 C5 C10 C9 0.1(7) . . . . ?
S2 C5 C10 C9 177.9(4) . . . . ?
C8 C9 C10 C5 -0.1(7) . . . . ?
N11 C9 C10 C5 -179.1(4) . . . . ?
C8 C9 N11 C12 128.1(5) . . . . ?
C10 C9 N11 C12 -52.9(7) . . . . ?
C8 C9 N11 C17 -66.1(6) . . . . ?
C10 C9 N11 C17 112.9(5) . . . . ?
C9 N11 C12 N14 168.1(4) . . . . ?
C17 N11 C12 N14 1.0(5) . . . . ?
C9 N11 C12 S13 -14.1(7) . . . . ?
C17 N11 C12 S13 178.8(3) . . . . ?
N11 C12 N14 C15 -2.7(5) . . . . ?
S13 C12 N14 C15 179.4(3) . . . . ?
N11 C12 N14 C20A -178.8(7) . . . . ?
S13 C12 N14 C20A 3.4(8) . . . . ?
N11 C12 N14 C20B -176.7(11) . . . . ?
S13 C12 N14 C20B 5.5(12) . . . . ?
C12 N14 C15 O16 -178.2(5) . . . . ?
C20A N14 C15 O16 -2.8(11) . . . . ?
C20B N14 C15 O16 -3.2(11) . . . . ?
C12 N14 C15 C17 3.3(5) . . . . ?
C20A N14 C15 C17 178.7(8) . . . . ?
C20B N14 C15 C17 178.3(9) . . . . ?
C12 N11 C17 C15 0.9(5) . . . . ?
C9 N11 C17 C15 -166.1(4) . . . . ?
C12 N11 C17 C19 117.3(4) . . . . ?
C9 N11 C17 C19 -49.7(6) . . . . ?
C12 N11 C17 C18 -114.9(5) . . . . ?
C9 N11 C17 C18 78.1(5) . . . . ?
O16 C15 C17 N11 179.1(5) . . . . ?
N14 C15 C17 N11 -2.4(5) . . . . ?
O16 C15 C17 C19 60.9(6) . . . . ?
N14 C15 C17 C19 -120.7(4) . . . . ?
O16 C15 C17 C18 -62.0(7) . . . . ?
N14 C15 C17 C18 116.4(4) . . . . ?
C15 N14 C20A C21A 117.2(11) . . . . ?
C12 N14 C20A C21A -67.6(13) . . . . ?
C20B N14 C20A C21A 119(5) . . . . ?
C15 N14 C20A C29A -49.0(17) . . . . ?
C12 N14 C20A C29A 126.2(14) . . . . ?
C20B N14 C20A C29A -47(5) . . . . ?
C29A C20A C21A C22A -8(2) . . . . ?
N14 C20A C21A C22A -174.3(10) . . . . ?
C20A C21A C22A C27A 7.3(18) . . . . ?
C20A C21A C22A C23A 178.3(11) . . . . ?
C21A C22A C23A F24A 1.2(15) . . . . ?
C27A C22A C23A F24A 172.4(11) . . . . ?
C21A C22A C23A F26A 125.5(12) . . . . ?
C27A C22A C23A F26A -63.4(14) . . . . ?
C21A C22A C23A F25A -115.9(13) . . . . ?
C27A C22A C23A F25A 55.2(15) . . . . ?
C21A C22A C27A C28A -6(2) . . . . ?
C23A C22A C27A C28A -177.2(12) . . . . ?
C21A C22A C27A C30A -172.7(12) . . . . ?
C23A C22A C27A C30A 16.3(18) . . . . ?
C22A C27A C28A C29A 6(2) . . . . ?
C30A C27A C28A C29A 172.7(17) . . . . ?
C27A C28A C29A C20A -7(3) . . . . ?
C21A C20A C29A C28A 8(3) . . . . ?
N14 C20A C29A C28A 174.4(16) . . . . ?
C28A C27A C30A N31A 61(34) . . . . ?
C22A C27A C30A N31A -132(33) . . . . ?
C15 N14 C20B C21B 130.3(17) . . . . ?
C12 N14 C20B C21B -56(2) . . . . ?
C20A N14 C20B C21B -48(4) . . . . ?
C15 N14 C20B C29B -62(2) . . . . ?
C12 N14 C20B C29B 111.5(18) . . . . ?
C20A N14 C20B C29B 119(6) . . . . ?
C29B C20B C21B C22B 5(3) . . . . ?
N14 C20B C21B C22B 172.3(16) . . . . ?
C20B C21B C22B C27B -5(3) . . . . ?
C20B C21B C22B C23B -179.9(17) . . . . ?
C21B C22B C23B F24B 18(2) . . . . ?
C27B C22B C23B F24B -157.2(17) . . . . ?
C21B C22B C23B F26B 139.9(16) . . . . ?
C27B C22B C23B F26B -35(2) . . . . ?
C21B C22B C23B F25B -101.7(18) . . . . ?
C27B C22B C23B F25B 84(2) . . . . ?
C21B C22B C27B C28B 9(3) . . . . ?
C23B C22B C27B C28B -175.8(15) . . . . ?
C21B C22B C27B C30B 167.4(18) . . . . ?
C23B C22B C27B C30B -18(3) . . . . ?
C22B C27B C28B C29B -14(3) . . . . ?
C30B C27B C28B C29B -173.3(19) . . . . ?
C27B C28B C29B C20B 14(3) . . . . ?
C21B C20B C29B C28B -10(4) . . . . ?
N14 C20B C29B C28B -176.8(18) . . . . ?
C28B C27B C30B N31B -13(58) . . . . ?
C22B C27B C30B N31B -172(100) . . . . ?
C106 C101 C102 C103 0.0 . . . . ?
C101 C102 C103 C104 0.0 . . . . ?
C102 C103 C104 C105 0.0 . . . . ?
C103 C104 C105 C106 0.0 . . . . ?
C104 C105 C106 C101 0.0 . . . . ?
C104 C105 C106 C107 179.1(7) . . . . ?
C102 C101 C106 C105 0.0 . . . . ?
C102 C101 C106 C107 -179.2(7) . . . . ?
C105 C106 C107 O108 161.9(12) . . . . ?
C101 C106 C107 O108 -18.9(14) . . . . ?
C105 C106 C107 O109 -16.0(13) . . . . ?
C101 C106 C107 O109 163.1(10) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O109 H109 N31B . . 1_454 3.06(2) 0.840 2.387 138.2 no
N1 H1A O3 . . 4_566 3.021(6) 0.92(2) 2.13(3) 161(5) no
N1 H1B N31A . . 1_454 2.932(12) 0.92(4) 2.07(4) 155(4) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_ZR_CH5134731_SU_004_1
_database_code_depnum_ccdc_archive 'CCDC 1540880'
_audit_update_record             
;
2017-10-27 deposited with the CCDC.
2017-12-11 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C21.5 H18 F3 N5 O3.5 S2'
_chemical_formula_moiety         'C21.5 H18 F3 N5 O3.5 S2'
_chemical_formula_weight         523.53
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   11.2994(2)
_cell_length_b                   20.5599(4)
_cell_length_c                   10.11464(18)
_cell_angle_alpha                90.0000
_cell_angle_beta                 92.3835(8)
_cell_angle_gamma                90.0000
_cell_volume                     2347.75(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    22395
_cell_measurement_theta_min      3.92
_cell_measurement_theta_max      68.23
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1036.00
_exptl_absorpt_coefficient_mu    2.550
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.809
_exptl_absorpt_correction_T_max  0.926

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            4297
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_theta_max         68.240
_diffrn_reflns_theta_min         3.916
_diffrn_reflns_theta_full        68.240
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4297
_reflns_number_gt                3804
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0376
_refine_ls_wR_factor_ref         0.1019
_refine_ls_wR_factor_gt          0.0971
_refine_ls_number_restraints     69
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         4297
_refine_ls_number_parameters     346
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0484P)²+1.8900P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.58
_refine_diff_density_min         -0.40
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.17555(16) 0.25849(9) -0.16306(17) 0.0216(4) Uani 1 1 d D . .
H1A H 0.192(2) 0.2695(11) -0.0758(12) 0.026 Uiso 1 1 d D . .
H1B H 0.1021(13) 0.2427(11) -0.189(2) 0.026 Uiso 1 1 d D . .
S2 S 0.28444(4) 0.22810(2) -0.23830(5) 0.01857(14) Uani 1 1 d . . .
O3 O 0.24711(14) 0.21890(7) -0.37447(14) 0.0258(3) Uani 1 1 d . . .
O4 O 0.38583(14) 0.26778(7) -0.20644(15) 0.0272(4) Uani 1 1 d . . .
C5 C 0.31506(17) 0.14982(9) -0.17154(19) 0.0167(4) Uani 1 1 d . . .
C6 C 0.30156(18) 0.09447(10) -0.24893(19) 0.0197(4) Uani 1 1 d . . .
H6 H 0.2761 0.0991 -0.3391 0.024 Uiso 1 1 calc R . .
N7 N 0.32305(15) 0.03476(8) -0.20143(16) 0.0204(4) Uani 1 1 d . . .
C8 C 0.35944(17) 0.02976(10) -0.07415(19) 0.0175(4) Uani 1 1 d . . .
H8 H 0.3749 -0.0124 -0.0391 0.021 Uiso 1 1 calc R . .
C9 C 0.37584(16) 0.08284(10) 0.00930(19) 0.0159(4) Uani 1 1 d . . .
C10 C 0.35326(17) 0.14470(10) -0.03940(19) 0.0176(4) Uani 1 1 d . . .
H10 H 0.3634 0.1821 0.0151 0.021 Uiso 1 1 calc R . .
N11 N 0.41519(14) 0.07368(8) 0.14395(15) 0.0155(3) Uani 1 1 d . . .
C12 C 0.51197(17) 0.10411(9) 0.19800(19) 0.0157(4) Uani 1 1 d . . .
S13 S 0.61446(4) 0.14392(2) 0.11928(5) 0.01848(14) Uani 1 1 d . . .
N14 N 0.51051(14) 0.09446(8) 0.33456(15) 0.0156(3) Uani 1 1 d . . .
C15 C 0.41093(17) 0.06011(9) 0.37081(19) 0.0168(4) Uani 1 1 d . . .
O16 O 0.38579(13) 0.04652(7) 0.48210(13) 0.0231(3) Uani 1 1 d . . .
C17 C 0.34132(17) 0.04234(9) 0.24405(19) 0.0164(4) Uani 1 1 d . . .
C18 C 0.33690(19) -0.03166(10) 0.2296(2) 0.0227(4) Uani 1 1 d . . .
H18A H 0.2882 -0.0500 0.2984 0.034 Uiso 1 1 calc R . .
H18B H 0.4174 -0.0493 0.2391 0.034 Uiso 1 1 calc R . .
H18C H 0.3023 -0.0430 0.1422 0.034 Uiso 1 1 calc R . .
C19 C 0.21719(17) 0.07183(11) 0.2439(2) 0.0225(4) Uani 1 1 d . . .
H19A H 0.1712 0.0502 0.3112 0.034 Uiso 1 1 calc R . .
H19B H 0.1777 0.0658 0.1567 0.034 Uiso 1 1 calc R . .
H19C H 0.2230 0.1184 0.2638 0.034 Uiso 1 1 calc R . .
C20 C 0.59720(17) 0.12039(9) 0.42682(19) 0.0167(4) Uani 1 1 d . . .
C21 C 0.71438(18) 0.10118(10) 0.4185(2) 0.0209(4) Uani 1 1 d . . .
H21 H 0.7359 0.0699 0.3547 0.025 Uiso 1 1 calc R . .
C22 C 0.79952(19) 0.12812(11) 0.5043(2) 0.0250(5) Uani 1 1 d . . .
C23 C 0.9265(2) 0.10705(14) 0.4979(3) 0.0381(6) Uani 1 1 d . . .
F24 F 0.94225(13) 0.06319(11) 0.40451(19) 0.0658(6) Uani 1 1 d . . .
F25 F 0.96590(13) 0.08051(9) 0.61181(17) 0.0547(5) Uani 1 1 d . . .
F26 F 0.99860(14) 0.15669(10) 0.4761(2) 0.0693(6) Uani 1 1 d . . .
C27 C 0.7652(2) 0.17355(10) 0.5999(2) 0.0261(5) Uani 1 1 d . . .
C28 C 0.6463(2) 0.18999(10) 0.6104(2) 0.0256(5) Uani 1 1 d . . .
H28 H 0.6233 0.2191 0.6777 0.031 Uiso 1 1 calc R . .
C29 C 0.56155(19) 0.16375(10) 0.5225(2) 0.0214(4) Uani 1 1 d . . .
H29 H 0.4805 0.1753 0.5278 0.026 Uiso 1 1 calc R . .
C30 C 0.8520(2) 0.20369(12) 0.6890(3) 0.0379(6) Uani 1 1 d . . .
N31 N 0.9211(2) 0.22796(12) 0.7582(3) 0.0553(7) Uani 1 1 d . . .
C101 C -0.0643(3) 0.0130(2) 0.1186(3) 0.0443(13) Uani 0.50 1 d PGU A -1
H101 H -0.0963 -0.0093 0.1913 0.053 Uiso 0.50 1 calc PR A -1
C102 C -0.0787(3) 0.0798(2) 0.1060(4) 0.0543(14) Uani 0.50 1 d PGU A -1
H102 H -0.1206 0.1033 0.1701 0.065 Uiso 0.50 1 calc PR A -1
C103 C -0.0319(4) 0.11238(18) -0.0004(5) 0.0545(18) Uani 0.50 1 d PGU A -1
H103 H -0.0418 0.1581 -0.0090 0.065 Uiso 0.50 1 calc PR A -1
C104 C 0.0293(4) 0.0780(3) -0.0942(4) 0.0569(17) Uani 0.50 1 d PGU A -1
H104 H 0.0612 0.1003 -0.1669 0.068 Uiso 0.50 1 calc PR A -1
C105 C 0.0437(4) 0.0111(2) -0.0816(3) 0.0438(14) Uani 0.50 1 d PGU A -1
H105 H 0.0855 -0.0123 -0.1458 0.053 Uiso 0.50 1 calc PR A -1
C106 C -0.0031(4) -0.02139(17) 0.0247(4) 0.0497(14) Uani 0.50 1 d PGDU A -1
O107 O 0.0048(5) -0.0855(3) 0.0462(5) 0.0565(12) Uani 0.50 1 d PDU A -1
C108 C 0.0632(8) -0.1276(4) -0.0448(8) 0.068(2) Uani 0.50 1 d PDU A -1
H10A H 0.0603 -0.1726 -0.0129 0.102 Uiso 0.50 1 calc PR A -1
H10B H 0.1459 -0.1141 -0.0510 0.102 Uiso 0.50 1 calc PR A -1
H10C H 0.0229 -0.1248 -0.1323 0.102 Uiso 0.50 1 calc PR A -1


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.2 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.2'

#==============================================================================
# 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
N1 S2 1.6004(18) . ?
N1 H1A 0.923(10) . ?
N1 H1B 0.918(10) . ?
S2 O4 1.4322(15) . ?
S2 O3 1.4361(15) . ?
S2 C5 1.774(2) . ?
C5 C6 1.386(3) . ?
C5 C10 1.391(3) . ?
C6 N7 1.337(3) . ?
C6 H6 0.9500 . ?
N7 C8 1.339(3) . ?
C8 C9 1.387(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.384(3) . ?
C9 N11 1.427(2) . ?
C10 H10 0.9500 . ?
N11 C12 1.355(2) . ?
N11 C17 1.486(2) . ?
C12 N14 1.396(2) . ?
C12 S13 1.650(2) . ?
N14 C15 1.391(2) . ?
N14 C20 1.428(2) . ?
C15 O16 1.205(2) . ?
C15 C17 1.521(3) . ?
C17 C19 1.528(3) . ?
C17 C18 1.529(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C21 1.388(3) . ?
C20 C29 1.388(3) . ?
C21 C22 1.384(3) . ?
C21 H21 0.9500 . ?
C22 C27 1.410(3) . ?
C22 C23 1.503(3) . ?
C23 F24 1.323(3) . ?
C23 F26 1.330(3) . ?
C23 F25 1.335(3) . ?
C27 C28 1.393(3) . ?
C27 C30 1.444(3) . ?
C28 C29 1.389(3) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C30 N31 1.142(3) . ?
C101 C102 1.3900 . ?
C101 C106 1.3900 . ?
C101 H101 0.9500 . ?
C102 C103 1.3900 . ?
C102 H102 0.9500 . ?
C103 C104 1.3900 . ?
C103 H103 0.9500 . ?
C104 C105 1.3900 . ?
C104 H104 0.9500 . ?
C105 C106 1.3900 . ?
C105 H105 0.9500 . ?
C106 O107 1.339(5) . ?
O107 C108 1.442(7) . ?
C108 H10A 0.9800 . ?
C108 H10B 0.9800 . ?
C108 H10C 0.9800 . ?

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
S2 N1 H1A 115.3(15) . . ?
S2 N1 H1B 115.6(16) . . ?
H1A N1 H1B 120(2) . . ?
O4 S2 O3 119.41(9) . . ?
O4 S2 N1 107.11(10) . . ?
O3 S2 N1 107.85(9) . . ?
O4 S2 C5 106.84(9) . . ?
O3 S2 C5 106.89(9) . . ?
N1 S2 C5 108.35(9) . . ?
C6 C5 C10 120.19(18) . . ?
C6 C5 S2 120.98(15) . . ?
C10 C5 S2 118.83(15) . . ?
N7 C6 C5 122.47(18) . . ?
N7 C6 H6 118.8 . . ?
C5 C6 H6 118.8 . . ?
C6 N7 C8 117.39(17) . . ?
N7 C8 C9 123.53(18) . . ?
N7 C8 H8 118.2 . . ?
C9 C8 H8 118.2 . . ?
C10 C9 C8 119.24(18) . . ?
C10 C9 N11 120.42(17) . . ?
C8 C9 N11 120.33(17) . . ?
C9 C10 C5 117.18(18) . . ?
C9 C10 H10 121.4 . . ?
C5 C10 H10 121.4 . . ?
C12 N11 C9 122.56(16) . . ?
C12 N11 C17 113.08(15) . . ?
C9 N11 C17 123.09(15) . . ?
N11 C12 N14 106.91(16) . . ?
N11 C12 S13 127.24(15) . . ?
N14 C12 S13 125.83(15) . . ?
C15 N14 C12 112.09(16) . . ?
C15 N14 C20 123.92(16) . . ?
C12 N14 C20 123.88(16) . . ?
O16 C15 N14 126.07(18) . . ?
O16 C15 C17 126.74(18) . . ?
N14 C15 C17 107.19(16) . . ?
N11 C17 C15 100.65(15) . . ?
N11 C17 C19 111.66(16) . . ?
C15 C17 C19 110.36(16) . . ?
N11 C17 C18 112.56(16) . . ?
C15 C17 C18 109.46(16) . . ?
C19 C17 C18 111.62(17) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C29 122.03(18) . . ?
C21 C20 N14 118.99(18) . . ?
C29 C20 N14 118.98(18) . . ?
C22 C21 C20 119.2(2) . . ?
C22 C21 H21 120.4 . . ?
C20 C21 H21 120.4 . . ?
C21 C22 C27 119.4(2) . . ?
C21 C22 C23 119.8(2) . . ?
C27 C22 C23 120.7(2) . . ?
F24 C23 F26 107.6(2) . . ?
F24 C23 F25 106.7(2) . . ?
F26 C23 F25 105.8(2) . . ?
F24 C23 C22 112.6(2) . . ?
F26 C23 C22 112.3(2) . . ?
F25 C23 C22 111.4(2) . . ?
C28 C27 C22 120.46(19) . . ?
C28 C27 C30 118.7(2) . . ?
C22 C27 C30 120.9(2) . . ?
C29 C28 C27 119.9(2) . . ?
C29 C28 H28 120.1 . . ?
C27 C28 H28 120.1 . . ?
C20 C29 C28 118.9(2) . . ?
C20 C29 H29 120.5 . . ?
C28 C29 H29 120.5 . . ?
N31 C30 C27 179.2(3) . . ?
C102 C101 C106 120.0 . . ?
C102 C101 H101 120.0 . . ?
C106 C101 H101 120.0 . . ?
C101 C102 C103 120.0 . . ?
C101 C102 H102 120.0 . . ?
C103 C102 H102 120.0 . . ?
C104 C103 C102 120.0 . . ?
C104 C103 H103 120.0 . . ?
C102 C103 H103 120.0 . . ?
C105 C104 C103 120.0 . . ?
C105 C104 H104 120.0 . . ?
C103 C104 H104 120.0 . . ?
C106 C105 C104 120.0 . . ?
C106 C105 H105 120.0 . . ?
C104 C105 H105 120.0 . . ?
O107 C106 C105 125.1(3) . . ?
O107 C106 C101 114.9(3) . . ?
C105 C106 C101 120.0 . . ?
C106 O107 C108 121.1(6) . . ?
O107 C108 H10A 109.5 . . ?
O107 C108 H10B 109.5 . . ?
H10A C108 H10B 109.5 . . ?
O107 C108 H10C 109.5 . . ?
H10A C108 H10C 109.5 . . ?
H10B C108 H10C 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
O4 S2 C5 C6 -128.77(17) . . . . ?
O3 S2 C5 C6 0.14(19) . . . . ?
N1 S2 C5 C6 116.12(17) . . . . ?
O4 S2 C5 C10 51.15(18) . . . . ?
O3 S2 C5 C10 -179.94(15) . . . . ?
N1 S2 C5 C10 -63.95(18) . . . . ?
C10 C5 C6 N7 0.6(3) . . . . ?
S2 C5 C6 N7 -179.50(16) . . . . ?
C5 C6 N7 C8 -0.3(3) . . . . ?
C6 N7 C8 C9 -0.1(3) . . . . ?
N7 C8 C9 C10 0.4(3) . . . . ?
N7 C8 C9 N11 -179.83(17) . . . . ?
C8 C9 C10 C5 -0.1(3) . . . . ?
N11 C9 C10 C5 -179.93(17) . . . . ?
C6 C5 C10 C9 -0.3(3) . . . . ?
S2 C5 C10 C9 179.76(14) . . . . ?
C10 C9 N11 C12 -54.8(3) . . . . ?
C8 C9 N11 C12 125.4(2) . . . . ?
C10 C9 N11 C17 111.5(2) . . . . ?
C8 C9 N11 C17 -68.3(2) . . . . ?
C9 N11 C12 N14 168.43(16) . . . . ?
C17 N11 C12 N14 1.0(2) . . . . ?
C9 N11 C12 S13 -12.7(3) . . . . ?
C17 N11 C12 S13 179.83(14) . . . . ?
N11 C12 N14 C15 -2.4(2) . . . . ?
S13 C12 N14 C15 178.74(14) . . . . ?
N11 C12 N14 C20 -178.66(16) . . . . ?
S13 C12 N14 C20 2.5(3) . . . . ?
C12 N14 C15 O16 -177.96(19) . . . . ?
C20 N14 C15 O16 -1.7(3) . . . . ?
C12 N14 C15 C17 2.8(2) . . . . ?
C20 N14 C15 C17 179.05(16) . . . . ?
C12 N11 C17 C15 0.6(2) . . . . ?
C9 N11 C17 C15 -166.77(16) . . . . ?
C12 N11 C17 C19 117.73(18) . . . . ?
C9 N11 C17 C19 -49.7(2) . . . . ?
C12 N11 C17 C18 -115.82(18) . . . . ?
C9 N11 C17 C18 76.8(2) . . . . ?
O16 C15 C17 N11 178.77(19) . . . . ?
N14 C15 C17 N11 -1.97(19) . . . . ?
O16 C15 C17 C19 60.7(3) . . . . ?
N14 C15 C17 C19 -120.03(17) . . . . ?
O16 C15 C17 C18 -62.5(3) . . . . ?
N14 C15 C17 C18 116.75(17) . . . . ?
C15 N14 C20 C21 122.1(2) . . . . ?
C12 N14 C20 C21 -62.1(3) . . . . ?
C15 N14 C20 C29 -57.6(3) . . . . ?
C12 N14 C20 C29 118.3(2) . . . . ?
C29 C20 C21 C22 -2.9(3) . . . . ?
N14 C20 C21 C22 177.44(18) . . . . ?
C20 C21 C22 C27 1.2(3) . . . . ?
C20 C21 C22 C23 179.1(2) . . . . ?
C21 C22 C23 F24 0.7(3) . . . . ?
C27 C22 C23 F24 178.5(2) . . . . ?
C21 C22 C23 F26 122.4(2) . . . . ?
C27 C22 C23 F26 -59.8(3) . . . . ?
C21 C22 C23 F25 -119.2(2) . . . . ?
C27 C22 C23 F25 58.6(3) . . . . ?
C21 C22 C27 C28 1.7(3) . . . . ?
C23 C22 C27 C28 -176.2(2) . . . . ?
C21 C22 C27 C30 -178.6(2) . . . . ?
C23 C22 C27 C30 3.5(3) . . . . ?
C22 C27 C28 C29 -2.9(3) . . . . ?
C30 C27 C28 C29 177.4(2) . . . . ?
C21 C20 C29 C28 1.7(3) . . . . ?
N14 C20 C29 C28 -178.66(18) . . . . ?
C27 C28 C29 C20 1.2(3) . . . . ?
C28 C27 C30 N31 -108(25) . . . . ?
C22 C27 C30 N31 73(25) . . . . ?
C106 C101 C102 C103 0.0 . . . . ?
C101 C102 C103 C104 0.0 . . . . ?
C102 C103 C104 C105 0.0 . . . . ?
C103 C104 C105 C106 0.0 . . . . ?
C104 C105 C106 O107 179.6(5) . . . . ?
C104 C105 C106 C101 0.0 . . . . ?
C102 C101 C106 O107 -179.6(5) . . . . ?
C102 C101 C106 C105 0.0 . . . . ?
C105 C106 O107 C108 -1.2(8) . . . . ?
C101 C106 O107 C108 178.4(6) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1A O3 . . 4_566 3.032(2) 0.922 2.119 170.4 no
N1 H1B N31 . . 1_454 3.017(3) 0.918 2.115 167.3 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_ZR_CH5134731_SU_001_1
_database_code_depnum_ccdc_archive 'CCDC 1540878'
_audit_update_record             
;
2017-10-27 deposited with the CCDC.
2017-12-11 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT420_ZR_CH5134731_SU_001_1 
;
PROBLEM: D-H Without Acceptor      *O108   -- *H108   ...     Please Check
RESPONSE: The solvent molecule including O108 and H108 has no acceptor because this molecule is disordered on the inversion center.
;
# Added during the CSD deposition process: Friday 27 October 2017 05:30 AM
# end Validation Reply Form


#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C21.5 H18 F3 N5 O3.5 S2'
_chemical_formula_moiety         'C21.5 H18 F3 N5 O3.5 S2'
_chemical_formula_weight         523.53
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   11.2642(2)
_cell_length_b                   20.5587(4)
_cell_length_c                   10.11845(18)
_cell_angle_alpha                90.0000
_cell_angle_beta                 91.9094(7)
_cell_angle_gamma                90.0000
_cell_volume                     2341.90(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    21882
_cell_measurement_theta_min      3.92
_cell_measurement_theta_max      68.24
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.030
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             960.00
_exptl_absorpt_coefficient_mu    2.534
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.808
_exptl_absorpt_correction_T_max  0.927

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            4245
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_theta_max         68.240
_diffrn_reflns_theta_min         3.927
_diffrn_reflns_theta_full        68.240
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4245
_reflns_number_gt                3746
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1075
_refine_ls_wR_factor_gt          0.1034
_refine_ls_number_restraints     73
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         4245
_refine_ls_number_parameters     349
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0450P)²+2.4016P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.43
_refine_diff_density_min         -0.41
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.17658(17) 0.25875(9) -0.15795(19) 0.0228(4) Uani 1 1 d D . .
H1A H 0.192(2) 0.2697(12) -0.0712(12) 0.027 Uiso 1 1 d D . .
H1B H 0.1030(13) 0.2411(12) -0.176(2) 0.027 Uiso 1 1 d D . .
S2 S 0.28576(5) 0.22849(2) -0.23434(5) 0.01987(15) Uani 1 1 d . . .
O3 O 0.24827(15) 0.21902(8) -0.36978(15) 0.0282(4) Uani 1 1 d . . .
O4 O 0.38708(14) 0.26865(8) -0.20429(16) 0.0281(4) Uani 1 1 d . . .
C5 C 0.31756(18) 0.15029(10) -0.1679(2) 0.0185(4) Uani 1 1 d . . .
C6 C 0.30492(19) 0.09494(10) -0.2457(2) 0.0201(4) Uani 1 1 d . . .
H6 H 0.2794 0.0996 -0.3356 0.024 Uiso 1 1 calc R . .
N7 N 0.32733(16) 0.03523(9) -0.19854(17) 0.0209(4) Uani 1 1 d . . .
C8 C 0.36298(18) 0.03020(10) -0.0717(2) 0.0186(4) Uani 1 1 d . . .
H8 H 0.3785 -0.0120 -0.0368 0.022 Uiso 1 1 calc R . .
C9 C 0.37860(18) 0.08344(10) 0.0122(2) 0.0170(4) Uani 1 1 d . . .
C10 C 0.35526(18) 0.14511(10) -0.0361(2) 0.0188(4) Uani 1 1 d . . .
H10 H 0.3646 0.1825 0.0186 0.023 Uiso 1 1 calc R . .
N11 N 0.41740(15) 0.07413(8) 0.14663(16) 0.0166(4) Uani 1 1 d . . .
C12 C 0.51509(18) 0.10429(10) 0.1998(2) 0.0165(4) Uani 1 1 d . . .
S13 S 0.61850(5) 0.14321(2) 0.11986(5) 0.02059(15) Uani 1 1 d . . .
N14 N 0.51269(15) 0.09507(8) 0.33639(17) 0.0169(4) Uani 1 1 d . . .
C15 C 0.41251(18) 0.06094(10) 0.3731(2) 0.0181(4) Uani 1 1 d . . .
O16 O 0.38667(14) 0.04759(8) 0.48465(14) 0.0255(4) Uani 1 1 d . . .
C17 C 0.34305(18) 0.04282(10) 0.2470(2) 0.0182(4) Uani 1 1 d . . .
C18 C 0.3402(2) -0.03150(10) 0.2336(2) 0.0233(5) Uani 1 1 d . . .
H18A H 0.2913 -0.0500 0.3026 0.035 Uiso 1 1 calc R . .
H18B H 0.4211 -0.0487 0.2431 0.035 Uiso 1 1 calc R . .
H18C H 0.3062 -0.0433 0.1465 0.035 Uiso 1 1 calc R . .
C19 C 0.21811(19) 0.07141(11) 0.2466(2) 0.0238(5) Uani 1 1 d . . .
H19A H 0.1720 0.0497 0.3142 0.036 Uiso 1 1 calc R . .
H19B H 0.1793 0.0648 0.1595 0.036 Uiso 1 1 calc R . .
H19C H 0.2228 0.1181 0.2658 0.036 Uiso 1 1 calc R . .
C20 C 0.59870(19) 0.12136(10) 0.4283(2) 0.0189(4) Uani 1 1 d . . .
C21 C 0.7166(2) 0.10332(12) 0.4186(2) 0.0248(5) Uani 1 1 d . . .
H21 H 0.7392 0.0725 0.3541 0.030 Uiso 1 1 calc R . .
C22 C 0.8009(2) 0.13068(13) 0.5041(2) 0.0309(6) Uani 1 1 d . . .
C23 C 0.9288(2) 0.11031(18) 0.4956(3) 0.0498(8) Uani 1 1 d . . .
F24 F 0.94732(17) 0.07244(18) 0.3958(2) 0.1162(12) Uani 1 1 d . . .
F25 F 0.96607(15) 0.07864(11) 0.6040(2) 0.0684(6) Uani 1 1 d . . .
F26 F 1.00097(17) 0.16127(14) 0.4890(3) 0.0973(9) Uani 1 1 d . . .
C27 C 0.7652(2) 0.17487(12) 0.6010(3) 0.0333(6) Uani 1 1 d . . .
C28 C 0.6459(2) 0.19038(11) 0.6127(2) 0.0316(6) Uani 1 1 d . . .
H28 H 0.6220 0.2189 0.6808 0.038 Uiso 1 1 calc R . .
C29 C 0.5616(2) 0.16396(11) 0.5244(2) 0.0249(5) Uani 1 1 d . . .
H29 H 0.4801 0.1750 0.5300 0.030 Uiso 1 1 calc R . .
C30 C 0.8508(3) 0.20471(16) 0.6915(3) 0.0530(8) Uani 1 1 d . . .
N31 N 0.9187(3) 0.22768(17) 0.7635(4) 0.0842(11) Uani 1 1 d . . .
C101 C 0.0658(3) -0.00438(19) -0.1026(4) 0.0374(14) Uani 0.50 1 d PGU A -1
H101 H 0.1176 -0.0188 -0.1687 0.045 Uiso 0.50 1 calc PR A -1
C102 C 0.0288(4) 0.06011(17) -0.1005(4) 0.0473(14) Uani 0.50 1 d PGU A -1
H102 H 0.0554 0.0898 -0.1651 0.057 Uiso 0.50 1 calc PR A -1
C103 C -0.0471(4) 0.08119(12) -0.0037(5) 0.0459(15) Uani 0.50 1 d PGU A -1
H103 H -0.0723 0.1253 -0.0023 0.055 Uiso 0.50 1 calc PR A -1
C104 C -0.0860(3) 0.03779(19) 0.0908(4) 0.0458(14) Uani 0.50 1 d PGU A -1
H104 H -0.1379 0.0522 0.1569 0.055 Uiso 0.50 1 calc PR A -1
C105 C -0.0490(4) -0.02670(16) 0.0887(4) 0.0389(14) Uani 0.50 1 d PGU A -1
H105 H -0.0757 -0.0564 0.1533 0.047 Uiso 0.50 1 calc PR A -1
C106 C 0.0268(4) -0.04779(12) -0.0080(5) 0.0443(13) Uani 0.50 1 d PGDU A -1
C107 C 0.0630(6) -0.1182(3) -0.0131(9) 0.0647(18) Uani 0.50 1 d PDU A -1
H10A H 0.1117 -0.1252 -0.0915 0.078 Uiso 0.50 1 calc PRD A -1
H10B H 0.1129 -0.1285 0.0665 0.078 Uiso 0.50 1 calc PR A -1
O108 O -0.0348(4) -0.1606(3) -0.0195(6) 0.0766(15) Uani 0.50 1 d PDU A -1
H108 H -0.034(5) -0.195(3) -0.074(7) 0.115 Uiso 0.50 1 d PD B -1


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.2 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.2'

#==============================================================================
# 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
N1 S2 1.6001(19) . ?
N1 H1A 0.918(10) . ?
N1 H1B 0.918(10) . ?
S2 O4 1.4331(16) . ?
S2 O3 1.4337(16) . ?
S2 C5 1.774(2) . ?
C5 C6 1.388(3) . ?
C5 C10 1.390(3) . ?
C6 N7 1.338(3) . ?
C6 H6 0.9500 . ?
N7 C8 1.336(3) . ?
C8 C9 1.392(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.381(3) . ?
C9 N11 1.428(3) . ?
C10 H10 0.9500 . ?
N11 C12 1.358(3) . ?
N11 C17 1.485(2) . ?
C12 N14 1.396(3) . ?
C12 S13 1.647(2) . ?
N14 C15 1.390(3) . ?
N14 C20 1.426(3) . ?
C15 O16 1.207(2) . ?
C15 C17 1.520(3) . ?
C17 C19 1.525(3) . ?
C17 C18 1.534(3) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C29 1.383(3) . ?
C20 C21 1.385(3) . ?
C21 C22 1.383(3) . ?
C21 H21 0.9500 . ?
C22 C27 1.405(4) . ?
C22 C23 1.505(4) . ?
C23 F24 1.297(4) . ?
C23 F26 1.329(4) . ?
C23 F25 1.332(3) . ?
C27 C28 1.390(4) . ?
C27 C30 1.445(4) . ?
C28 C29 1.393(3) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C30 N31 1.141(4) . ?
C101 C102 1.3900 . ?
C101 C106 1.3900 . ?
C101 H101 0.9500 . ?
C102 C103 1.3900 . ?
C102 H102 0.9500 . ?
C103 C104 1.3900 . ?
C103 H103 0.9500 . ?
C104 C105 1.3900 . ?
C104 H104 0.9500 . ?
C105 C106 1.3900 . ?
C105 H105 0.9500 . ?
C106 C107 1.504(6) . ?
C107 O108 1.405(7) . ?
C107 H10A 0.9900 . ?
C107 H10B 0.9900 . ?
O108 H108 0.895(10) . ?

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
S2 N1 H1A 115.4(16) . . ?
S2 N1 H1B 116.9(16) . . ?
H1A N1 H1B 116(2) . . ?
O4 S2 O3 119.22(10) . . ?
O4 S2 N1 107.03(10) . . ?
O3 S2 N1 107.93(10) . . ?
O4 S2 C5 107.00(10) . . ?
O3 S2 C5 106.77(10) . . ?
N1 S2 C5 108.54(10) . . ?
C6 C5 C10 120.2(2) . . ?
C6 C5 S2 120.80(17) . . ?
C10 C5 S2 118.96(16) . . ?
N7 C6 C5 122.4(2) . . ?
N7 C6 H6 118.8 . . ?
C5 C6 H6 118.8 . . ?
C8 N7 C6 117.42(18) . . ?
N7 C8 C9 123.54(19) . . ?
N7 C8 H8 118.2 . . ?
C9 C8 H8 118.2 . . ?
C10 C9 C8 119.19(19) . . ?
C10 C9 N11 120.56(18) . . ?
C8 C9 N11 120.25(18) . . ?
C9 C10 C5 117.26(19) . . ?
C9 C10 H10 121.4 . . ?
C5 C10 H10 121.4 . . ?
C12 N11 C9 122.29(17) . . ?
C12 N11 C17 113.27(16) . . ?
C9 N11 C17 123.25(16) . . ?
N11 C12 N14 106.72(17) . . ?
N11 C12 S13 127.17(16) . . ?
N14 C12 S13 126.10(16) . . ?
C15 N14 C12 112.06(17) . . ?
C15 N14 C20 123.87(17) . . ?
C12 N14 C20 123.95(17) . . ?
O16 C15 N14 126.0(2) . . ?
O16 C15 C17 126.56(19) . . ?
N14 C15 C17 107.43(17) . . ?
N11 C17 C15 100.45(16) . . ?
N11 C17 C19 111.87(17) . . ?
C15 C17 C19 110.92(17) . . ?
N11 C17 C18 112.47(16) . . ?
C15 C17 C18 109.09(17) . . ?
C19 C17 C18 111.51(18) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C29 C20 C21 122.1(2) . . ?
C29 C20 N14 118.92(19) . . ?
C21 C20 N14 118.98(19) . . ?
C22 C21 C20 119.2(2) . . ?
C22 C21 H21 120.4 . . ?
C20 C21 H21 120.4 . . ?
C21 C22 C27 119.5(2) . . ?
C21 C22 C23 119.3(3) . . ?
C27 C22 C23 121.1(2) . . ?
F24 C23 F26 108.6(3) . . ?
F24 C23 F25 107.1(3) . . ?
F26 C23 F25 104.5(2) . . ?
F24 C23 C22 113.0(2) . . ?
F26 C23 C22 111.8(3) . . ?
F25 C23 C22 111.4(2) . . ?
C28 C27 C22 120.6(2) . . ?
C28 C27 C30 118.4(3) . . ?
C22 C27 C30 121.1(3) . . ?
C27 C28 C29 119.7(2) . . ?
C27 C28 H28 120.1 . . ?
C29 C28 H28 120.1 . . ?
C20 C29 C28 118.9(2) . . ?
C20 C29 H29 120.6 . . ?
C28 C29 H29 120.6 . . ?
N31 C30 C27 179.3(4) . . ?
C102 C101 C106 120.0 . . ?
C102 C101 H101 120.0 . . ?
C106 C101 H101 120.0 . . ?
C103 C102 C101 120.0 . . ?
C103 C102 H102 120.0 . . ?
C101 C102 H102 120.0 . . ?
C102 C103 C104 120.0 . . ?
C102 C103 H103 120.0 . . ?
C104 C103 H103 120.0 . . ?
C105 C104 C103 120.0 . . ?
C105 C104 H104 120.0 . . ?
C103 C104 H104 120.0 . . ?
C104 C105 C106 120.0 . . ?
C104 C105 H105 120.0 . . ?
C106 C105 H105 120.0 . . ?
C105 C106 C101 120.0 . . ?
C105 C106 C107 119.8(4) . . ?
C101 C106 C107 120.1(4) . . ?
O108 C107 C106 112.7(5) . . ?
O108 C107 H10A 109.0 . . ?
C106 C107 H10A 109.0 . . ?
O108 C107 H10B 109.0 . . ?
C106 C107 H10B 109.0 . . ?
H10A C107 H10B 107.8 . . ?
C107 O108 H108 119.7(16) . . ?

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
O4 S2 C5 C6 -128.27(18) . . . . ?
O3 S2 C5 C6 0.4(2) . . . . ?
N1 S2 C5 C6 116.54(18) . . . . ?
O4 S2 C5 C10 51.87(19) . . . . ?
O3 S2 C5 C10 -179.44(16) . . . . ?
N1 S2 C5 C10 -63.32(19) . . . . ?
C10 C5 C6 N7 0.3(3) . . . . ?
S2 C5 C6 N7 -179.53(16) . . . . ?
C5 C6 N7 C8 0.0(3) . . . . ?
C6 N7 C8 C9 -0.5(3) . . . . ?
N7 C8 C9 C10 0.7(3) . . . . ?
N7 C8 C9 N11 -179.77(18) . . . . ?
C8 C9 C10 C5 -0.3(3) . . . . ?
N11 C9 C10 C5 -179.84(18) . . . . ?
C6 C5 C10 C9 -0.2(3) . . . . ?
S2 C5 C10 C9 179.71(15) . . . . ?
C10 C9 N11 C12 -55.8(3) . . . . ?
C8 C9 N11 C12 124.6(2) . . . . ?
C10 C9 N11 C17 110.8(2) . . . . ?
C8 C9 N11 C17 -68.7(3) . . . . ?
C9 N11 C12 N14 168.12(17) . . . . ?
C17 N11 C12 N14 0.2(2) . . . . ?
C9 N11 C12 S13 -12.9(3) . . . . ?
C17 N11 C12 S13 179.18(15) . . . . ?
N11 C12 N14 C15 -1.9(2) . . . . ?
S13 C12 N14 C15 179.16(15) . . . . ?
N11 C12 N14 C20 -177.88(18) . . . . ?
S13 C12 N14 C20 3.1(3) . . . . ?
C12 N14 C15 O16 -178.2(2) . . . . ?
C20 N14 C15 O16 -2.1(3) . . . . ?
C12 N14 C15 C17 2.7(2) . . . . ?
C20 N14 C15 C17 178.71(18) . . . . ?
C12 N11 C17 C15 1.3(2) . . . . ?
C9 N11 C17 C15 -166.49(17) . . . . ?
C12 N11 C17 C19 119.01(19) . . . . ?
C9 N11 C17 C19 -48.8(3) . . . . ?
C12 N11 C17 C18 -114.6(2) . . . . ?
C9 N11 C17 C18 77.7(2) . . . . ?
O16 C15 C17 N11 178.6(2) . . . . ?
N14 C15 C17 N11 -2.3(2) . . . . ?
O16 C15 C17 C19 60.1(3) . . . . ?
N14 C15 C17 C19 -120.72(18) . . . . ?
O16 C15 C17 C18 -63.1(3) . . . . ?
N14 C15 C17 C18 116.07(18) . . . . ?
C15 N14 C20 C29 -56.2(3) . . . . ?
C12 N14 C20 C29 119.4(2) . . . . ?
C15 N14 C20 C21 123.6(2) . . . . ?
C12 N14 C20 C21 -60.8(3) . . . . ?
C29 C20 C21 C22 -2.7(3) . . . . ?
N14 C20 C21 C22 177.45(19) . . . . ?
C20 C21 C22 C27 1.6(3) . . . . ?
C20 C21 C22 C23 178.9(2) . . . . ?
C21 C22 C23 F24 6.7(4) . . . . ?
C27 C22 C23 F24 -176.1(3) . . . . ?
C21 C22 C23 F26 129.6(3) . . . . ?
C27 C22 C23 F26 -53.1(3) . . . . ?
C21 C22 C23 F25 -113.9(3) . . . . ?
C27 C22 C23 F25 63.3(4) . . . . ?
C21 C22 C27 C28 1.0(4) . . . . ?
C23 C22 C27 C28 -176.2(2) . . . . ?
C21 C22 C27 C30 -179.7(2) . . . . ?
C23 C22 C27 C30 3.1(4) . . . . ?
C22 C27 C28 C29 -2.6(4) . . . . ?
C30 C27 C28 C29 178.0(2) . . . . ?
C21 C20 C29 C28 1.1(3) . . . . ?
N14 C20 C29 C28 -179.03(19) . . . . ?
C27 C28 C29 C20 1.5(3) . . . . ?
C28 C27 C30 N31 117(38) . . . . ?
C22 C27 C30 N31 -62(38) . . . . ?
C106 C101 C102 C103 0.0 . . . . ?
C101 C102 C103 C104 0.0 . . . . ?
C102 C103 C104 C105 0.0 . . . . ?
C103 C104 C105 C106 0.0 . . . . ?
C104 C105 C106 C101 0.0 . . . . ?
C104 C105 C106 C107 -177.7(5) . . . . ?
C102 C101 C106 C105 0.0 . . . . ?
C102 C101 C106 C107 177.7(5) . . . . ?
C105 C106 C107 O108 54.4(8) . . . . ?
C101 C106 C107 O108 -123.3(6) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1A O3 . . 4_566 3.034(2) 0.918(14) 2.126(14) 170(2) no
N1 H1B N31 . . 1_454 3.054(4) 0.918(17) 2.163(16) 164(2) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
####################################################################### 
# 
# 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_ZR_CH5134731_SU_003_1
_database_code_depnum_ccdc_archive 'CCDC 1540879'
_audit_update_record             
;
2017-10-27 deposited with the CCDC.
2017-12-11 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C21 H16.5 Cl0.5 F3 N5 O3 S2'
_chemical_formula_moiety         'C21 H16.5 Cl0.5 F3 N5 O3 S2'
_chemical_formula_weight         525.73
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   11.24851(18)
_cell_length_b                   20.6292(4)
_cell_length_c                   10.0577(2)
_cell_angle_alpha                90.0000
_cell_angle_beta                 91.7969(9)
_cell_angle_gamma                90.0000
_cell_volume                     2332.73(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    18082
_cell_measurement_theta_min      3.93
_cell_measurement_theta_max      68.19
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.497
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1076.00
_exptl_absorpt_coefficient_mu    3.126
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.732
_exptl_absorpt_correction_T_max  0.939

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54187
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            4265
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_theta_max         68.200
_diffrn_reflns_theta_min         3.932
_diffrn_reflns_theta_full        68.200
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4265
_reflns_number_gt                3296
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1917
_refine_ls_wR_factor_gt          0.1352
_refine_ls_number_restraints     63
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         4265
_refine_ls_number_parameters     337
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.1100P)²+2.5683P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.54
_refine_diff_density_min         -0.54
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0492 0.0322
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0311 0.0180
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.3331 0.5567
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
F F 0.0727 0.0534
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.3639 0.7018
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.1790(3) 0.25906(15) -0.1624(3) 0.0245(7) Uani 1 1 d D . .
H1A H 0.181(3) 0.2664(18) -0.0722(12) 0.029 Uiso 1 1 d D . .
H1B H 0.1020(16) 0.2449(19) -0.178(3) 0.029 Uiso 1 1 d D . .
S2 S 0.28790(8) 0.22801(4) -0.23755(8) 0.0218(3) Uani 1 1 d . . .
O3 O 0.2509(2) 0.21879(12) -0.3741(2) 0.0285(6) Uani 1 1 d . . .
O4 O 0.3907(2) 0.26692(12) -0.2068(2) 0.0290(6) Uani 1 1 d . . .
C5 C 0.3167(3) 0.15006(17) -0.1702(3) 0.0207(7) Uani 1 1 d . . .
C6 C 0.2983(3) 0.09455(18) -0.2472(3) 0.0230(7) Uani 1 1 d . . .
H6 H 0.2704 0.0992 -0.3368 0.028 Uiso 1 1 calc R . .
N7 N 0.3186(3) 0.03488(14) -0.1992(3) 0.0243(7) Uani 1 1 d . . .
C8 C 0.3569(3) 0.02998(17) -0.0723(3) 0.0220(7) Uani 1 1 d . . .
H8 H 0.3707 -0.0122 -0.0370 0.026 Uiso 1 1 calc R . .
C9 C 0.3779(3) 0.08271(16) 0.0107(3) 0.0197(7) Uani 1 1 d . . .
C10 C 0.3568(3) 0.14461(17) -0.0384(3) 0.0214(7) Uani 1 1 d . . .
H10 H 0.3691 0.1819 0.0159 0.026 Uiso 1 1 calc R . .
N11 N 0.4185(2) 0.07369(13) 0.1449(2) 0.0178(6) Uani 1 1 d . . .
C12 C 0.5157(3) 0.10408(16) 0.1978(3) 0.0196(7) Uani 1 1 d . . .
S13 S 0.61894(8) 0.14304(4) 0.11680(8) 0.0233(3) Uani 1 1 d . . .
N14 N 0.5141(2) 0.09523(13) 0.3355(2) 0.0183(6) Uani 1 1 d . . .
C15 C 0.4136(3) 0.06096(16) 0.3738(3) 0.0200(7) Uani 1 1 d . . .
O16 O 0.3888(2) 0.04787(12) 0.4862(2) 0.0257(6) Uani 1 1 d . . .
C17 C 0.3443(3) 0.04254(16) 0.2473(3) 0.0190(7) Uani 1 1 d . . .
C18 C 0.3409(3) -0.03119(17) 0.2343(3) 0.0257(8) Uani 1 1 d . . .
H18A H 0.2960 -0.0432 0.1530 0.039 Uiso 1 1 calc R . .
H18B H 0.3023 -0.0498 0.3116 0.039 Uiso 1 1 calc R . .
H18C H 0.4223 -0.0479 0.2302 0.039 Uiso 1 1 calc R . .
C19 C 0.2195(3) 0.07152(18) 0.2483(3) 0.0253(8) Uani 1 1 d . . .
H19A H 0.1753 0.0590 0.1668 0.038 Uiso 1 1 calc R . .
H19B H 0.2250 0.1189 0.2531 0.038 Uiso 1 1 calc R . .
H19C H 0.1779 0.0553 0.3258 0.038 Uiso 1 1 calc R . .
C20 C 0.6009(3) 0.12198(16) 0.4271(3) 0.0200(7) Uani 1 1 d . . .
C21 C 0.7185(3) 0.10268(18) 0.4178(3) 0.0258(8) Uani 1 1 d . . .
H21 H 0.7403 0.0712 0.3540 0.031 Uiso 1 1 calc R . .
C22 C 0.8032(3) 0.13006(19) 0.5028(4) 0.0299(8) Uani 1 1 d . . .
C23 C 0.9311(4) 0.1081(3) 0.4940(5) 0.0527(13) Uani 1 1 d . . .
F24 F 0.9482(3) 0.0680(2) 0.3973(4) 0.1084(16) Uani 1 1 d . . .
F25 F 0.9679(3) 0.07862(17) 0.6072(4) 0.0798(11) Uani 1 1 d . . .
F26 F 1.0050(2) 0.15851(18) 0.4823(4) 0.0777(11) Uani 1 1 d . . .
C27 C 0.7682(3) 0.17469(18) 0.5993(4) 0.0320(9) Uani 1 1 d . . .
C28 C 0.6497(4) 0.19094(18) 0.6109(4) 0.0317(9) Uani 1 1 d . . .
H28 H 0.6262 0.2199 0.6786 0.038 Uiso 1 1 calc R . .
C29 C 0.5648(3) 0.16454(17) 0.5227(3) 0.0251(8) Uani 1 1 d . . .
H29 H 0.4833 0.1758 0.5286 0.030 Uiso 1 1 calc R . .
C30 C 0.8550(4) 0.2053(2) 0.6881(5) 0.0454(11) Uani 1 1 d . . .
N31 N 0.9234(4) 0.2292(2) 0.7585(5) 0.0663(14) Uani 1 1 d . . .
C51 C 0.0564(7) -0.0184(3) -0.1117(6) 0.056(2) Uani 0.50 1 d PGDU A -1
H51 H 0.0834 0.0060 -0.1850 0.068 Uiso 0.50 1 calc PR A -1
C52 C 0.0791(6) -0.0845(3) -0.1042(6) 0.062(2) Uani 0.50 1 d PGU A -1
H52 H 0.1216 -0.1053 -0.1723 0.075 Uiso 0.50 1 calc PR A -1
C53 C 0.0396(7) -0.1202(2) 0.0030(7) 0.054(3) Uani 0.50 1 d PGU A -1
H53 H 0.0551 -0.1654 0.0082 0.065 Uiso 0.50 1 calc PR A -1
C54 C -0.0225(6) -0.0897(3) 0.1027(6) 0.0473(19) Uani 0.50 1 d PGU A -1
H54 H -0.0495 -0.1141 0.1760 0.057 Uiso 0.50 1 calc PR A -1
C55 C -0.0452(6) -0.0236(3) 0.0951(5) 0.0384(16) Uani 0.50 1 d PGDU A -1
H55 H -0.0877 -0.0028 0.1632 0.046 Uiso 0.50 1 calc PR A -1
C56 C -0.0057(8) 0.0121(2) -0.0121(7) 0.0544(19) Uani 0.50 1 d PGDU A -1
Cl57 Cl -0.0363(4) 0.09425(17) -0.0247(3) 0.0845(11) Uani 0.50 1 d PDU A -1


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR2004 (Burla, et al., 2005)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2.2 (Rigaku, 2016)'
_computing_molecular_graphics    'CrystalStructure 4.2.2'

#==============================================================================
# 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
N1 S2 1.594(3) . ?
N1 H1A 0.919(10) . ?
N1 H1B 0.923(10) . ?
S2 O4 1.433(3) . ?
S2 O3 1.436(2) . ?
S2 C5 1.771(3) . ?
C5 C10 1.392(4) . ?
C5 C6 1.394(5) . ?
C6 N7 1.339(5) . ?
C6 H6 0.9500 . ?
N7 C8 1.338(4) . ?
C8 C9 1.387(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.387(5) . ?
C9 N11 1.423(4) . ?
C10 H10 0.9500 . ?
N11 C12 1.354(4) . ?
N11 C17 1.491(4) . ?
C12 N14 1.397(4) . ?
C12 S13 1.649(3) . ?
N14 C15 1.398(4) . ?
N14 C20 1.432(4) . ?
C15 O16 1.203(4) . ?
C15 C17 1.519(4) . ?
C17 C19 1.527(5) . ?
C17 C18 1.527(5) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C20 C29 1.373(5) . ?
C20 C21 1.387(5) . ?
C21 C22 1.381(5) . ?
C21 H21 0.9500 . ?
C22 C27 1.402(6) . ?
C22 C23 1.514(6) . ?
C23 F24 1.296(6) . ?
C23 F26 1.339(6) . ?
C23 F25 1.344(6) . ?
C27 C28 1.384(6) . ?
C27 C30 1.448(5) . ?
C28 C29 1.393(5) . ?
C28 H28 0.9500 . ?
C29 H29 0.9500 . ?
C30 N31 1.140(5) . ?
C51 C52 1.3900 . ?
C51 C56 1.3900 . ?
C51 H51 0.9500 . ?
C52 C53 1.3900 . ?
C52 H52 0.9500 . ?
C53 C54 1.3900 . ?
C53 H53 0.9500 . ?
C54 C55 1.3900 . ?
C54 H54 0.9500 . ?
C55 C56 1.3900 . ?
C55 H55 0.9500 . ?
C56 Cl57 1.733(5) . ?

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
S2 N1 H1A 123(2) . . ?
S2 N1 H1B 121(2) . . ?
H1A N1 H1B 102(2) . . ?
O4 S2 O3 119.23(16) . . ?
O4 S2 N1 107.42(16) . . ?
O3 S2 N1 107.63(16) . . ?
O4 S2 C5 106.84(16) . . ?
O3 S2 C5 106.84(15) . . ?
N1 S2 C5 108.51(16) . . ?
C10 C5 C6 120.0(3) . . ?
C10 C5 S2 119.2(3) . . ?
C6 C5 S2 120.8(3) . . ?
N7 C6 C5 122.3(3) . . ?
N7 C6 H6 118.8 . . ?
C5 C6 H6 118.8 . . ?
C8 N7 C6 117.3(3) . . ?
N7 C8 C9 124.0(3) . . ?
N7 C8 H8 118.0 . . ?
C9 C8 H8 118.0 . . ?
C10 C9 C8 118.9(3) . . ?
C10 C9 N11 120.3(3) . . ?
C8 C9 N11 120.8(3) . . ?
C9 C10 C5 117.4(3) . . ?
C9 C10 H10 121.3 . . ?
C5 C10 H10 121.3 . . ?
C12 N11 C9 122.9(3) . . ?
C12 N11 C17 113.0(2) . . ?
C9 N11 C17 122.8(3) . . ?
N11 C12 N14 107.1(3) . . ?
N11 C12 S13 127.1(2) . . ?
N14 C12 S13 125.8(3) . . ?
C12 N14 C15 112.0(3) . . ?
C12 N14 C20 123.9(3) . . ?
C15 N14 C20 124.0(3) . . ?
O16 C15 N14 125.8(3) . . ?
O16 C15 C17 127.1(3) . . ?
N14 C15 C17 107.1(3) . . ?
N11 C17 C15 100.8(3) . . ?
N11 C17 C19 111.8(3) . . ?
C15 C17 C19 110.1(3) . . ?
N11 C17 C18 112.5(3) . . ?
C15 C17 C18 109.3(3) . . ?
C19 C17 C18 111.7(3) . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C29 C20 C21 122.3(3) . . ?
C29 C20 N14 119.1(3) . . ?
C21 C20 N14 118.6(3) . . ?
C22 C21 C20 118.8(3) . . ?
C22 C21 H21 120.6 . . ?
C20 C21 H21 120.6 . . ?
C21 C22 C27 119.6(3) . . ?
C21 C22 C23 118.7(4) . . ?
C27 C22 C23 121.6(4) . . ?
F24 C23 F26 108.8(4) . . ?
F24 C23 F25 107.3(5) . . ?
F26 C23 F25 104.5(4) . . ?
F24 C23 C22 113.5(4) . . ?
F26 C23 C22 111.5(4) . . ?
F25 C23 C22 110.7(4) . . ?
C28 C27 C22 120.6(3) . . ?
C28 C27 C30 118.4(4) . . ?
C22 C27 C30 121.0(4) . . ?
C27 C28 C29 119.6(4) . . ?
C27 C28 H28 120.2 . . ?
C29 C28 H28 120.2 . . ?
C20 C29 C28 118.9(3) . . ?
C20 C29 H29 120.5 . . ?
C28 C29 H29 120.5 . . ?
N31 C30 C27 179.7(5) . . ?
C52 C51 C56 120.0 . . ?
C52 C51 H51 120.0 . . ?
C56 C51 H51 120.0 . . ?
C51 C52 C53 120.0 . . ?
C51 C52 H52 120.0 . . ?
C53 C52 H52 120.0 . . ?
C54 C53 C52 120.0 . . ?
C54 C53 H53 120.0 . . ?
C52 C53 H53 120.0 . . ?
C55 C54 C53 120.0 . . ?
C55 C54 H54 120.0 . . ?
C53 C54 H54 120.0 . . ?
C54 C55 C56 120.0 . . ?
C54 C55 H55 120.0 . . ?
C56 C55 H55 120.0 . . ?
C55 C56 C51 120.0 . . ?
C55 C56 Cl57 120.5(4) . . ?
C51 C56 Cl57 119.5(4) . . ?

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
O4 S2 C5 C10 50.1(3) . . . . ?
O3 S2 C5 C10 178.7(3) . . . . ?
N1 S2 C5 C10 -65.5(3) . . . . ?
O4 S2 C5 C6 -130.7(3) . . . . ?
O3 S2 C5 C6 -2.0(3) . . . . ?
N1 S2 C5 C6 113.8(3) . . . . ?
C10 C5 C6 N7 -0.4(5) . . . . ?
S2 C5 C6 N7 -179.6(3) . . . . ?
C5 C6 N7 C8 0.5(5) . . . . ?
C6 N7 C8 C9 -0.8(5) . . . . ?
N7 C8 C9 C10 1.0(5) . . . . ?
N7 C8 C9 N11 179.8(3) . . . . ?
C8 C9 C10 C5 -0.8(5) . . . . ?
N11 C9 C10 C5 -179.7(3) . . . . ?
C6 C5 C10 C9 0.6(5) . . . . ?
S2 C5 C10 C9 179.8(3) . . . . ?
C10 C9 N11 C12 -53.4(4) . . . . ?
C8 C9 N11 C12 127.8(3) . . . . ?
C10 C9 N11 C17 112.3(4) . . . . ?
C8 C9 N11 C17 -66.5(4) . . . . ?
C9 N11 C12 N14 167.5(3) . . . . ?
C17 N11 C12 N14 0.5(4) . . . . ?
C9 N11 C12 S13 -13.8(5) . . . . ?
C17 N11 C12 S13 179.3(2) . . . . ?
N11 C12 N14 C15 -2.1(4) . . . . ?
S13 C12 N14 C15 179.1(2) . . . . ?
N11 C12 N14 C20 -178.1(3) . . . . ?
S13 C12 N14 C20 3.1(5) . . . . ?
C12 N14 C15 O16 -178.4(3) . . . . ?
C20 N14 C15 O16 -2.4(5) . . . . ?
C12 N14 C15 C17 2.9(4) . . . . ?
C20 N14 C15 C17 178.8(3) . . . . ?
C12 N11 C17 C15 1.1(3) . . . . ?
C9 N11 C17 C15 -165.9(3) . . . . ?
C12 N11 C17 C19 118.1(3) . . . . ?
C9 N11 C17 C19 -48.9(4) . . . . ?
C12 N11 C17 C18 -115.2(3) . . . . ?
C9 N11 C17 C18 77.8(4) . . . . ?
O16 C15 C17 N11 178.9(3) . . . . ?
N14 C15 C17 N11 -2.3(3) . . . . ?
O16 C15 C17 C19 60.8(4) . . . . ?
N14 C15 C17 C19 -120.5(3) . . . . ?
O16 C15 C17 C18 -62.4(4) . . . . ?
N14 C15 C17 C18 116.4(3) . . . . ?
C12 N14 C20 C29 119.1(4) . . . . ?
C15 N14 C20 C29 -56.4(4) . . . . ?
C12 N14 C20 C21 -62.4(4) . . . . ?
C15 N14 C20 C21 122.1(3) . . . . ?
C29 C20 C21 C22 -3.8(5) . . . . ?
N14 C20 C21 C22 177.8(3) . . . . ?
C20 C21 C22 C27 2.3(5) . . . . ?
C20 C21 C22 C23 179.0(4) . . . . ?
C21 C22 C23 F24 4.9(6) . . . . ?
C27 C22 C23 F24 -178.4(4) . . . . ?
C21 C22 C23 F26 128.2(4) . . . . ?
C27 C22 C23 F26 -55.1(6) . . . . ?
C21 C22 C23 F25 -115.9(5) . . . . ?
C27 C22 C23 F25 60.8(6) . . . . ?
C21 C22 C27 C28 0.8(6) . . . . ?
C23 C22 C27 C28 -175.9(4) . . . . ?
C21 C22 C27 C30 -178.7(4) . . . . ?
C23 C22 C27 C30 4.7(6) . . . . ?
C22 C27 C28 C29 -2.4(6) . . . . ?
C30 C27 C28 C29 177.0(4) . . . . ?
C21 C20 C29 C28 2.1(5) . . . . ?
N14 C20 C29 C28 -179.4(3) . . . . ?
C27 C28 C29 C20 1.0(5) . . . . ?
C28 C27 C30 N31 103(100) . . . . ?
C22 C27 C30 N31 -78(100) . . . . ?
C56 C51 C52 C53 0.0 . . . . ?
C51 C52 C53 C54 0.0 . . . . ?
C52 C53 C54 C55 0.0 . . . . ?
C53 C54 C55 C56 0.0 . . . . ?
C54 C55 C56 C51 0.0 . . . . ?
C54 C55 C56 Cl57 178.5(7) . . . . ?
C52 C51 C56 C55 0.0 . . . . ?
C52 C51 C56 Cl57 -178.5(7) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N1 H1A O3 . . 4_566 3.020(4) 0.919(14) 2.140(17) 160(3) no
N1 H1B N31 . . 1_454 3.023(5) 0.92(2) 2.11(2) 168(3) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
