# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_RZ-OA-270K
_database_code_depnum_ccdc_archive 'CCDC 1572075'
_audit_update_record             
;
2017-09-01 deposited with the CCDC.
2018-03-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H6 F3 N2 O3 S'
_chemical_formula_weight         279.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.7557(4)
_cell_length_b                   10.0386(4)
_cell_length_c                   11.7809(4)
_cell_angle_alpha                90
_cell_angle_beta                 100.132(3)
_cell_angle_gamma                90
_cell_volume                     1135.75(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    270(2)
_cell_measurement_reflns_used    2757
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      26.77

_exptl_crystal_description       Plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_F_000             564
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.328
_shelx_estimated_absorpt_T_min   0.867
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_process_details   'SADABS 2014/4'
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7510
_exptl_absorpt_correction_T_min  0.5086
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      270(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11948
_diffrn_reflns_av_unetI/netI     0.0358
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.121
_diffrn_reflns_theta_max         29.626
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3175
_reflns_number_gt                2055
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1326P)²+0.5926P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3175
_refine_ls_number_parameters     175
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1072
_refine_ls_R_factor_gt           0.0753
_refine_ls_wR_factor_ref         0.2453
_refine_ls_wR_factor_gt          0.2202
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.33648(10) 0.58197(8) 0.30793(7) 0.0586(3) Uani 1 1 d . . . . .
F1 F -0.0859(5) 0.7175(9) 0.6675(6) 0.235(4) Uani 1 1 d . . . . .
F2 F -0.0981(4) 0.7920(5) 0.4985(5) 0.178(2) Uani 1 1 d . . . . .
F3 F -0.0757(4) 0.9302(6) 0.6339(6) 0.210(3) Uani 1 1 d . . . . .
O1 O 0.0972(3) 0.8046(4) 0.6200(4) 0.1119(14) Uani 1 1 d . . . . .
O2 O 0.4806(3) 1.0824(2) 0.36849(17) 0.0678(8) Uani 1 1 d . . . . .
O3 O 0.4552(3) 1.1589(2) 0.54080(16) 0.0604(7) Uani 1 1 d . . . . .
N1 N 0.4504(3) 0.3436(3) 0.2803(2) 0.0522(7) Uani 1 1 d . . . . .
H1B H 0.476(4) 0.255(4) 0.304(3) 0.063(10) Uiso 1 1 d . . . . .
H1A H 0.456(4) 0.374(4) 0.213(4) 0.062(10) Uiso 1 1 d . . . . .
N2 N 0.3675(3) 0.3865(3) 0.44987(19) 0.0458(6) Uani 1 1 d . . . . .
H2 H 0.394(4) 0.317(4) 0.488(3) 0.062(10) Uiso 1 1 d . . . . .
C1 C 0.3918(3) 0.4216(3) 0.3459(2) 0.0423(6) Uani 1 1 d . . . . .
C2 C 0.2965(3) 0.4832(3) 0.5016(2) 0.0491(7) Uani 1 1 d . . . . .
C3 C 0.2525(4) 0.4737(4) 0.6068(3) 0.0682(10) Uani 1 1 d . . . . .
H3 H 0.269143 0.397121 0.651518 0.082 Uiso 1 1 calc R U . . .
C4 C 0.1832(5) 0.5811(5) 0.6434(4) 0.0814(13) Uani 1 1 d . . . . .
H4 H 0.151965 0.577461 0.713532 0.098 Uiso 1 1 calc R U . . .
C5 C 0.1607(4) 0.6926(5) 0.5765(4) 0.0749(12) Uani 1 1 d . . . . .
C6 C 0.2025(4) 0.7051(4) 0.4729(4) 0.0687(10) Uani 1 1 d . . . . .
H6 H 0.185861 0.782491 0.429288 0.082 Uiso 1 1 calc R U . . .
C7 C 0.2706(3) 0.5978(3) 0.4353(3) 0.0528(7) Uani 1 1 d . . . . .
C8 C -0.0326(6) 0.8145(9) 0.6003(9) 0.145(3) Uani 1 1 d . . . . .
C9 C 0.4818(3) 1.0693(3) 0.4733(2) 0.0461(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.732(3) . ?
S1 C7 1.740(3) . ?
F1 C8 1.411(12) . ?
F2 C8 1.275(9) . ?
F3 C8 1.320(7) . ?
O1 C8 1.250(7) . ?
O1 C5 1.423(5) . ?
O2 C9 1.239(3) . ?
O3 C9 1.258(3) . ?
N1 C1 1.301(4) . ?
N1 H1B 0.95(4) . ?
N1 H1A 0.86(4) . ?
N2 C1 1.335(3) . ?
N2 C2 1.394(4) . ?
N2 H2 0.84(4) . ?
C2 C3 1.384(4) . ?
C2 C7 1.388(4) . ?
C3 C4 1.382(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.364(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.359(6) . ?
C6 C7 1.379(5) . ?
C6 H6 0.9300 . ?
C9 C9 1.542(5) 3_676 ?

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 C7 90.44(14) . . ?
C8 O1 C5 119.1(4) . . ?
C1 N1 H1B 121(2) . . ?
C1 N1 H1A 116(3) . . ?
H1B N1 H1A 123(4) . . ?
C1 N2 C2 113.5(2) . . ?
C1 N2 H2 128(3) . . ?
C2 N2 H2 118(3) . . ?
N1 C1 N2 123.6(3) . . ?
N1 C1 S1 123.7(2) . . ?
N2 C1 S1 112.6(2) . . ?
C3 C2 C7 120.5(3) . . ?
C3 C2 N2 126.8(3) . . ?
C7 C2 N2 112.7(3) . . ?
C4 C3 C2 118.1(4) . . ?
C4 C3 H3 120.9 . . ?
C2 C3 H3 120.9 . . ?
C5 C4 C3 119.8(4) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C6 C5 C4 123.5(4) . . ?
C6 C5 O1 118.0(5) . . ?
C4 C5 O1 118.4(4) . . ?
C5 C6 C7 117.0(4) . . ?
C5 C6 H6 121.5 . . ?
C7 C6 H6 121.5 . . ?
C6 C7 C2 121.1(3) . . ?
C6 C7 S1 128.3(3) . . ?
C2 C7 S1 110.6(2) . . ?
O1 C8 F2 119.0(6) . . ?
O1 C8 F3 112.3(5) . . ?
F2 C8 F3 107.7(8) . . ?
O1 C8 F1 107.6(8) . . ?
F2 C8 F1 103.4(6) . . ?
F3 C8 F1 105.7(7) . . ?
O2 C9 O3 125.9(3) . . ?
O2 C9 C9 117.7(3) . 3_676 ?
O3 C9 C9 116.4(3) . 3_676 ?

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
C2 N2 C1 N1 -176.4(3) . . . . ?
C2 N2 C1 S1 3.3(3) . . . . ?
C7 S1 C1 N1 177.0(3) . . . . ?
C7 S1 C1 N2 -2.8(2) . . . . ?
C1 N2 C2 C3 177.6(3) . . . . ?
C1 N2 C2 C7 -2.1(4) . . . . ?
C7 C2 C3 C4 -0.2(6) . . . . ?
N2 C2 C3 C4 -180.0(4) . . . . ?
C2 C3 C4 C5 -0.3(6) . . . . ?
C3 C4 C5 C6 0.4(7) . . . . ?
C3 C4 C5 O1 -176.0(4) . . . . ?
C8 O1 C5 C6 93.8(8) . . . . ?
C8 O1 C5 C4 -89.7(8) . . . . ?
C4 C5 C6 C7 0.2(6) . . . . ?
O1 C5 C6 C7 176.5(3) . . . . ?
C5 C6 C7 C2 -0.8(6) . . . . ?
C5 C6 C7 S1 179.9(3) . . . . ?
C3 C2 C7 C6 0.8(5) . . . . ?
N2 C2 C7 C6 -179.4(3) . . . . ?
C3 C2 C7 S1 -179.8(3) . . . . ?
N2 C2 C7 S1 0.0(4) . . . . ?
C1 S1 C7 C6 -179.1(4) . . . . ?
C1 S1 C7 C2 1.5(3) . . . . ?
C5 O1 C8 F2 -45.4(12) . . . . ?
C5 O1 C8 F3 -172.5(7) . . . . ?
C5 O1 C8 F1 71.6(8) . . . . ?

_refine_diff_density_max         0.850
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.077

####################################################################### 
# 
# 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_RZ-OA-225K
_database_code_depnum_ccdc_archive 'CCDC 1572076'
_audit_update_record             
;
2017-09-01 deposited with the CCDC.
2018-03-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H6 F3 N2 O3 S'
_chemical_formula_weight         279.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.6547(5)
_cell_length_b                   10.0570(5)
_cell_length_c                   11.7482(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.553(4)
_cell_angle_gamma                90
_cell_volume                     1121.42(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1828
_cell_measurement_theta_min      3.78
_cell_measurement_theta_max      25.67

_exptl_crystal_description       Plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.654
_exptl_crystal_F_000             564
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.332
_shelx_estimated_absorpt_T_min   0.865
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_process_details   'SADABS 2014/4'
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7510
_exptl_absorpt_correction_T_min  0.5086
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7885
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_av_R_equivalents  0.0288
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.779
_diffrn_reflns_theta_max         28.698
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             2877
_reflns_number_gt                1983
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0639P)²+0.3490P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2877
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0768
_refine_ls_R_factor_gt           0.0510
_refine_ls_wR_factor_ref         0.1424
_refine_ls_wR_factor_gt          0.1260
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.33613(8) -0.08177(6) 0.30723(5) 0.0549(2) Uani 1 1 d . . . . .
F1A F -0.1050(4) -0.2867(6) 0.5008(6) 0.1272(19) Uani 0.785(7) 1 d . . P A 1
F2A F -0.0897(4) -0.2170(6) 0.6682(4) 0.183(3) Uani 0.785(7) 1 d . . P A 1
F3A F -0.0788(6) -0.4216(8) 0.6428(8) 0.201(4) Uani 0.785(7) 1 d . . P A 1
O1A O 0.1005(4) -0.3077(5) 0.6199(5) 0.0923(18) Uani 0.785(7) 1 d . . P A 1
C5A C 0.1654(6) -0.1921(8) 0.5773(7) 0.065(2) Uani 0.785(7) 1 d . . P A 1
C6A C 0.2046(6) -0.2100(7) 0.4743(6) 0.0547(15) Uani 0.785(7) 1 d . . P A 1
H6A H 0.190621 -0.289293 0.433012 0.066 Uiso 0.785(7) 1 calc R U P A 1
C8A C -0.0421(12) -0.3121(19) 0.6048(15) 0.139(6) Uani 0.785(7) 1 d . . P A 1
F1B F -0.0788(17) -0.3553(17) 0.4494(14) 0.100(5) Uani 0.215(7) 1 d . . P A 2
F2B F 0.0888(17) -0.4537(11) 0.5350(12) 0.134(6) Uani 0.215(7) 1 d . . P A 2
F3B F -0.078(2) -0.4540(13) 0.6032(13) 0.081(4) Uani 0.215(7) 1 d . . P A 2
O1B O 0.037(3) -0.274(2) 0.6051(16) 0.094(6) Uani 0.215(7) 1 d . . P A 2
C5B C 0.120(2) -0.188(3) 0.5633(19) 0.054(6) Uani 0.215(7) 1 d . . P A 2
C6B C 0.178(3) -0.180(2) 0.453(2) 0.065(7) Uani 0.215(7) 1 d . . P A 2
H6B H 0.144188 -0.240731 0.394721 0.078 Uiso 0.215(7) 1 calc R U P A 2
C8B C -0.018(4) -0.352(5) 0.560(3) 0.104(13) Uani 0.215(7) 1 d . . P A 2
O2 O 0.5439(2) -0.34127(14) 0.45901(12) 0.0553(5) Uani 1 1 d . . . . .
O3 O 0.5197(2) -0.41740(15) 0.63186(12) 0.0616(5) Uani 1 1 d . . . . .
N1 N 0.4508(2) 0.1567(2) 0.28047(16) 0.0501(5) Uani 1 1 d . . . . .
H1B H 0.469(3) 0.246(3) 0.306(2) 0.065(8) Uiso 1 1 d . . . . .
H1A H 0.463(3) 0.130(3) 0.214(3) 0.077(9) Uiso 1 1 d . . . . .
N2 N 0.3671(2) 0.11338(19) 0.44983(14) 0.0448(5) Uani 1 1 d . . . . .
H2 H 0.395(3) 0.202(3) 0.484(2) 0.070(8) Uiso 1 1 d . . . . .
C1 C 0.3918(2) 0.0784(2) 0.34604(17) 0.0417(5) Uani 1 1 d . . . . .
C2 C 0.2949(3) 0.0168(2) 0.50084(18) 0.0473(5) Uani 1 1 d . . . . .
C3 C 0.2508(3) 0.0269(3) 0.6066(2) 0.0654(7) Uani 1 1 d . . . . .
H3 H 0.267790 0.103122 0.651821 0.078 Uiso 1 1 calc R U . . .
C4 C 0.1803(4) -0.0815(4) 0.6419(3) 0.0783(10) Uani 1 1 d . . . . .
H4 H 0.143799 -0.077367 0.709743 0.094 Uiso 1 1 calc R U . A 1
C7 C 0.2693(3) -0.0970(2) 0.4344(2) 0.0505(6) Uani 1 1 d . . . . .
C9 C 0.5183(3) -0.4305(2) 0.52695(16) 0.0433(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.733(2) . ?
S1 C7 1.739(2) . ?
F1A C8A 1.286(17) . ?
F2A C8A 1.343(19) . ?
F3A C8A 1.263(16) . ?
O1A C8A 1.357(12) . ?
O1A C5A 1.453(9) . ?
C5A C4 1.340(9) . ?
C5A C6A 1.344(10) . ?
C6A C7 1.417(6) . ?
C6A H6A 0.9300 . ?
F1B C8B 1.32(4) . ?
F2B C8B 1.52(5) . ?
F3B C8B 1.33(4) . ?
O1B C8B 1.04(4) . ?
O1B C5B 1.33(3) . ?
C5B C4 1.46(2) . ?
C5B C6B 1.50(3) . ?
C6B C7 1.26(3) . ?
C6B H6B 0.9300 . ?
O2 C9 1.256(2) . ?
O3 C9 1.237(2) . ?
N1 C1 1.303(3) . ?
N1 H1B 0.95(3) . ?
N1 H1A 0.85(3) . ?
N2 C1 1.332(2) . ?
N2 C2 1.393(3) . ?
N2 H2 0.99(3) . ?
C2 C7 1.382(3) . ?
C2 C3 1.388(3) . ?
C3 C4 1.388(4) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C9 C9 1.548(4) 3_646 ?

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 C7 90.10(10) . . ?
C8A O1A C5A 118.2(7) . . ?
C4 C5A C6A 127.0(6) . . ?
C4 C5A O1A 118.5(6) . . ?
C6A C5A O1A 114.5(7) . . ?
C5A C6A C7 113.8(6) . . ?
C5A C6A H6A 123.1 . . ?
C7 C6A H6A 123.1 . . ?
F3A C8A F1A 113.2(16) . . ?
F3A C8A F2A 106.2(8) . . ?
F1A C8A F2A 103.6(10) . . ?
F3A C8A O1A 109.0(10) . . ?
F1A C8A O1A 114.1(8) . . ?
F2A C8A O1A 110.3(15) . . ?
C8B O1B C5B 126(3) . . ?
O1B C5B C4 116.1(16) . . ?
O1B C5B C6B 134(2) . . ?
C4 C5B C6B 109.5(18) . . ?
C7 C6B C5B 125(2) . . ?
C7 C6B H6B 117.7 . . ?
C5B C6B H6B 117.7 . . ?
O1B C8B F1B 128(4) . . ?
O1B C8B F3B 128(3) . . ?
F1B C8B F3B 102(3) . . ?
O1B C8B F2B 108(4) . . ?
F1B C8B F2B 89(3) . . ?
F3B C8B F2B 85(3) . . ?
C1 N1 H1B 117.2(16) . . ?
C1 N1 H1A 120(2) . . ?
H1B N1 H1A 122(3) . . ?
C1 N2 C2 113.41(18) . . ?
C1 N2 H2 121.8(16) . . ?
C2 N2 H2 124.7(16) . . ?
N1 C1 N2 123.6(2) . . ?
N1 C1 S1 123.64(15) . . ?
N2 C1 S1 112.79(15) . . ?
C7 C2 C3 120.9(2) . . ?
C7 C2 N2 112.73(17) . . ?
C3 C2 N2 126.4(2) . . ?
C4 C3 C2 117.2(3) . . ?
C4 C3 H3 121.4 . . ?
C2 C3 H3 121.4 . . ?
C5A C4 C3 119.4(4) . . ?
C3 C4 C5B 123.2(9) . . ?
C5A C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C6B C7 C2 120.6(11) . . ?
C2 C7 C6A 121.5(4) . . ?
C6B C7 S1 126.0(11) . . ?
C2 C7 S1 110.86(16) . . ?
C6A C7 S1 127.6(4) . . ?
O3 C9 O2 126.11(19) . . ?
O3 C9 C9 117.6(2) . 3_646 ?
O2 C9 C9 116.2(2) . 3_646 ?

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
C8A O1A C5A C4 80.8(12) . . . . ?
C8A O1A C5A C6A -99.2(12) . . . . ?
C4 C5A C6A C7 0.6(9) . . . . ?
O1A C5A C6A C7 -179.3(4) . . . . ?
C5A O1A C8A F3A 177.3(10) . . . . ?
C5A O1A C8A F1A 49.6(19) . . . . ?
C5A O1A C8A F2A -66.6(11) . . . . ?
C8B O1B C5B C4 176(4) . . . . ?
C8B O1B C5B C6B -10(6) . . . . ?
O1B C5B C6B C7 -171(3) . . . . ?
C4 C5B C6B C7 3(3) . . . . ?
C5B O1B C8B F1B -35(7) . . . . ?
C5B O1B C8B F3B 165(4) . . . . ?
C5B O1B C8B F2B 68(4) . . . . ?
C2 N2 C1 N1 176.1(2) . . . . ?
C2 N2 C1 S1 -3.6(3) . . . . ?
C7 S1 C1 N1 -176.7(2) . . . . ?
C7 S1 C1 N2 2.9(2) . . . . ?
C1 N2 C2 C7 2.4(3) . . . . ?
C1 N2 C2 C3 -177.8(3) . . . . ?
C7 C2 C3 C4 -0.1(4) . . . . ?
N2 C2 C3 C4 -179.9(3) . . . . ?
C6A C5A C4 C3 -4.4(8) . . . . ?
O1A C5A C4 C3 175.6(4) . . . . ?
C2 C3 C4 C5A 3.9(5) . . . . ?
C2 C3 C4 C5B -16.2(13) . . . . ?
O1B C5B C4 C3 -170.0(17) . . . . ?
C6B C5B C4 C3 15(2) . . . . ?
C5B C6B C7 C2 -18(3) . . . . ?
C5B C6B C7 S1 -178.3(16) . . . . ?
C3 C2 C7 C6B 17.1(13) . . . . ?
N2 C2 C7 C6B -163.1(13) . . . . ?
C3 C2 C7 C6A -3.7(5) . . . . ?
N2 C2 C7 C6A 176.1(3) . . . . ?
C3 C2 C7 S1 -179.9(2) . . . . ?
N2 C2 C7 S1 -0.1(3) . . . . ?
C5A C6A C7 C2 3.4(7) . . . . ?
C5A C6A C7 S1 179.0(4) . . . . ?
C1 S1 C7 C6B 160.3(14) . . . . ?
C1 S1 C7 C2 -1.5(2) . . . . ?
C1 S1 C7 C6A -177.5(4) . . . . ?

_refine_diff_density_max         0.313
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_RZ-OA-100K
_database_code_depnum_ccdc_archive 'CCDC 1572079'
_audit_update_record             
;
2017-11-20 deposited with the CCDC.
2018-03-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H12 F6 N4 O6 S2'
_chemical_formula_weight         558.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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'

_cell_length_a                   18.786(3)
_cell_length_b                   20.184(3)
_cell_length_c                   11.6566(17)
_cell_angle_alpha                90
_cell_angle_beta                 101.624(9)
_cell_angle_gamma                90
_cell_volume                     4329.4(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2858
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      29.77

_exptl_crystal_description       Plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.713
_exptl_crystal_F_000             2256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.344
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_process_details   'SADABS 2014/4'
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.5119
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            9372
_diffrn_reflns_av_unetI/netI     0.2519
_diffrn_reflns_av_R_equivalents  0.1434
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.494
_diffrn_reflns_theta_max         29.571
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.580
_diffrn_reflns_point_group_measured_fraction_full 0.594
_reflns_number_total             7045
_reflns_number_gt                3956
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.159
_reflns_Friedel_fraction_max     0.159
_reflns_Friedel_fraction_full    0.187

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0140P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.19(13)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         7045
_refine_ls_number_parameters     687
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1697
_refine_ls_R_factor_gt           0.0736
_refine_ls_wR_factor_ref         0.1626
_refine_ls_wR_factor_gt          0.1309
_refine_ls_goodness_of_fit_ref   0.940
_refine_ls_restrained_S_all      0.940
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.39587(12) 0.08847(9) 0.54237(15) 0.0180(4) Uani 1 1 d . . . . .
S2 S 0.56985(12) -0.16145(9) 0.42955(16) 0.0199(5) Uani 1 1 d . . . . .
S3 S 0.58586(12) 0.66399(9) 0.94077(16) 0.0207(5) Uani 1 1 d . . . . .
S4 S 0.42923(11) 0.42508(9) 0.05268(15) 0.0175(4) Uani 1 1 d . . . . .
F1 F 0.1947(3) -0.1020(3) 0.8471(4) 0.0435(16) Uani 1 1 d . . . . .
F2 F 0.1939(3) -0.0555(3) 0.6815(4) 0.0427(15) Uani 1 1 d . . . . .
F3 F 0.2903(3) -0.1051(2) 0.7710(4) 0.0331(13) Uani 1 1 d . . . . .
F4 F 0.8037(3) -0.2479(2) 0.2311(4) 0.0282(11) Uani 1 1 d . . . . .
F5 F 0.7929(3) -0.3061(3) 0.0736(5) 0.0387(14) Uani 1 1 d . . . . .
F6 F 0.7884(3) -0.1988(3) 0.0651(4) 0.0350(13) Uani 1 1 d . . . . .
F7 F 0.7915(3) 0.7525(3) 0.5566(5) 0.0399(14) Uani 1 1 d . . . . .
F8 F 0.8052(3) 0.7849(2) 0.7338(4) 0.0358(13) Uani 1 1 d . . . . .
F9 F 0.7744(3) 0.8546(3) 0.5942(5) 0.0469(16) Uani 1 1 d . . . . .
F10 F 0.2015(3) 0.6049(3) 0.3379(5) 0.0406(14) Uani 1 1 d . . . . .
F11 F 0.1952(3) 0.5301(3) 0.2058(5) 0.0478(16) Uani 1 1 d . . . . .
F12 F 0.1943(4) 0.5021(3) 0.3805(6) 0.0519(17) Uani 1 1 d . . . . .
O1 O 0.2552(4) -0.0123(3) 0.8479(5) 0.0289(15) Uani 1 1 d . . . . .
O2 O 0.5219(3) 0.4119(2) 0.8834(4) 0.0198(13) Uani 1 1 d . . . . .
O3 O 0.5333(3) 0.4510(2) 0.7081(4) 0.0204(13) Uani 1 1 d . . . . .
O4 O 0.4871(3) 0.3337(3) 0.6102(4) 0.0229(14) Uani 1 1 d . . . . .
O5 O 0.4788(3) 0.2943(2) 0.7863(5) 0.0220(13) Uani 1 1 d . . . . .
O6 O 0.6972(3) -0.2581(3) 0.1090(5) 0.0262(14) Uani 1 1 d . . . . .
O7 O 0.4875(4) 0.0852(2) 0.3713(5) 0.0247(14) Uani 1 1 d . . . . .
O8 O 0.4970(4) 0.0479(2) 0.1943(5) 0.0282(15) Uani 1 1 d . . . . .
O9 O 0.4738(4) 0.2109(3) 0.2864(5) 0.0261(14) Uani 1 1 d . . . . .
O10 O 0.4811(4) 0.1719(3) 0.1094(5) 0.0258(15) Uani 1 1 d . . . . .
O11 O 0.6938(3) 0.7845(3) 0.6220(5) 0.0265(14) Uani 1 1 d . . . . .
O12 O 0.2953(3) 0.5448(3) 0.3410(5) 0.0242(13) Uani 1 1 d . . . . .
N1 N 0.4627(4) 0.2050(3) 0.5221(6) 0.0180(15) Uani 1 1 d . . . . .
H1A H 0.475(5) 0.187(4) 0.457(7) 0.022 Uiso 1 1 d . U . . .
H1B H 0.470(5) 0.248(4) 0.538(7) 0.022 Uiso 1 1 d . U . . .
N2 N 0.4196(4) 0.1828(3) 0.6922(5) 0.0156(14) Uani 1 1 d . . . . .
H2 H 0.438(4) 0.221(4) 0.724(7) 0.019 Uiso 1 1 d . U . . .
N3 N 0.5032(4) -0.0467(3) 0.4581(6) 0.0175(15) Uani 1 1 d . . . . .
H3A H 0.491(5) 0.000(4) 0.440(7) 0.021 Uiso 1 1 d . U . . .
H3B H 0.489(5) -0.065(4) 0.515(7) 0.021 Uiso 1 1 d . U . . .
N4 N 0.5458(4) -0.0628(3) 0.2869(5) 0.0173(15) Uani 1 1 d . . . . .
H4 H 0.517(6) -0.019(5) 0.239(8) 0.05(3) Uiso 1 1 d . . . . .
N5 N 0.5378(4) 0.5421(3) 0.9703(6) 0.0189(15) Uani 1 1 d . . . . .
H5A H 0.526(5) 0.500(4) 0.943(7) 0.023 Uiso 1 1 d . U . . .
H5B H 0.519(5) 0.558(4) 1.028(7) 0.023 Uiso 1 1 d . U . . .
N6 N 0.5833(3) 0.5638(3) 0.8036(5) 0.0125(13) Uani 1 1 d . . . . .
H6 H 0.559(4) 0.510(4) 0.758(6) 0.02(2) Uiso 1 1 d . . . . .
N7 N 0.4801(4) 0.3019(3) 0.0297(6) 0.0175(15) Uani 1 1 d . . . . .
H7A H 0.486(5) 0.266(4) 0.051(8) 0.021 Uiso 1 1 d . U . . .
H7B H 0.490(5) 0.310(4) -0.046(7) 0.021 Uiso 1 1 d . U . . .
N8 N 0.4375(4) 0.3293(3) 0.1997(6) 0.0156(14) Uani 1 1 d . . . . .
H8 H 0.454(5) 0.294(4) 0.221(7) 0.019 Uiso 1 1 d . U . . .
C1 C 0.4298(5) 0.1669(4) 0.5861(6) 0.0179(18) Uani 1 1 d . . . . .
C2 C 0.3792(4) 0.1369(3) 0.7407(6) 0.0137(16) Uani 1 1 d . . . . .
C5 C 0.2988(5) 0.0354(4) 0.8053(7) 0.0204(18) Uani 1 1 d . . . . .
C6 C 0.3212(4) 0.0286(4) 0.7003(6) 0.0169(17) Uani 1 1 d . . . . .
H6A H 0.310283 -0.009576 0.652267 0.020 Uiso 1 1 calc R U . . .
C12 C 0.5845(5) -0.1070(4) 0.2353(6) 0.0192(18) Uani 1 1 d . . . . .
C35 C 0.3928(4) 0.4361(4) 0.1775(6) 0.0130(15) Uani 1 1 d . . . . .
C29 C 0.4520(4) 0.3438(4) 0.0937(6) 0.0162(17) Uani 1 1 d . . . . .
C22 C 0.6147(4) 0.6141(3) 0.7497(6) 0.0164(17) Uani 1 1 d . . . . .
C7 C 0.3613(4) 0.0819(4) 0.6693(6) 0.0164(17) Uani 1 1 d . . . . .
C21 C 0.5657(4) 0.5815(3) 0.9052(6) 0.0160(17) Uani 1 1 d . . . . .
C9 C 0.5177(5) 0.4061(4) 0.7757(6) 0.0161(17) Uani 1 1 d . . . . .
C26 C 0.6481(5) 0.7298(4) 0.7739(7) 0.024(2) Uani 1 1 d . . . . .
H26 H 0.650596 0.770522 0.815444 0.029 Uiso 1 1 calc R U . . .
C4 C 0.3139(5) 0.0905(4) 0.8763(7) 0.0215(18) Uani 1 1 d . . . . .
H4A H 0.295525 0.093426 0.946292 0.026 Uiso 1 1 calc R U . . .
C34 C 0.3574(4) 0.4921(4) 0.2069(6) 0.0192(17) Uani 1 1 d . . . . .
H34 H 0.352272 0.531060 0.160182 0.023 Uiso 1 1 calc R U . . .
C13 C 0.6046(5) -0.0998(4) 0.1265(7) 0.024(2) Uani 1 1 d . . . . .
H13 H 0.591364 -0.060969 0.081119 0.029 Uiso 1 1 calc R U . . .
C10 C 0.4921(5) 0.3390(4) 0.7188(7) 0.0189(18) Uani 1 1 d . . . . .
C28 C 0.7632(6) 0.7932(4) 0.6279(8) 0.031(2) Uani 1 1 d . . . . .
C18 C 0.7687(5) -0.2517(4) 0.1210(8) 0.032(2) Uani 1 1 d . . . . .
C33 C 0.3298(5) 0.4877(4) 0.3087(7) 0.0207(18) Uani 1 1 d . . . . .
C23 C 0.6381(5) 0.6100(4) 0.6457(7) 0.0217(18) Uani 1 1 d . . . . .
H23 H 0.635185 0.569523 0.603568 0.026 Uiso 1 1 calc R U . . .
C20 C 0.4803(5) 0.1651(4) 0.2160(7) 0.0169(17) Uani 1 1 d . . . . .
C32 C 0.3399(5) 0.4323(4) 0.3797(7) 0.0213(18) Uani 1 1 d . . . . .
H32 H 0.321404 0.431921 0.449830 0.026 Uiso 1 1 calc R U . . .
C3 C 0.3555(5) 0.1414(4) 0.8459(6) 0.0218(19) Uani 1 1 d . . . . .
H3 H 0.367635 0.178703 0.895705 0.026 Uiso 1 1 calc R U . . .
C16 C 0.6417(4) -0.2152(4) 0.2596(7) 0.0204(17) Uani 1 1 d . . . . .
H16 H 0.654570 -0.254575 0.303422 0.025 Uiso 1 1 calc R U . . .
C30 C 0.4029(4) 0.3795(4) 0.2472(6) 0.0159(16) Uani 1 1 d . . . . .
C11 C 0.5356(4) -0.0831(3) 0.3918(6) 0.0154(16) Uani 1 1 d . . . . .
C31 C 0.3764(4) 0.3777(4) 0.3503(6) 0.0181(17) Uani 1 1 d . . . . .
H31 H 0.383280 0.339697 0.399285 0.022 Uiso 1 1 calc R U . . .
C25 C 0.6713(4) 0.7244(4) 0.6691(7) 0.0189(17) Uani 1 1 d . . . . .
C15 C 0.6598(4) -0.2053(4) 0.1529(7) 0.0220(18) Uani 1 1 d . . . . .
C19 C 0.4891(5) 0.0934(4) 0.2664(6) 0.0208(19) Uani 1 1 d . . . . .
C17 C 0.6035(5) -0.1642(4) 0.3001(7) 0.0190(17) Uani 1 1 d . . . . .
C36 C 0.2239(5) 0.5445(4) 0.3168(8) 0.031(2) Uani 1 1 d . . . . .
C27 C 0.6213(4) 0.6733(4) 0.8147(7) 0.0182(18) Uani 1 1 d . . . . .
C24 C 0.6661(5) 0.6666(4) 0.6037(7) 0.0197(18) Uani 1 1 d . . . . .
H24 H 0.681567 0.665725 0.531000 0.024 Uiso 1 1 calc R U . . .
C8 C 0.2352(5) -0.0679(4) 0.7865(7) 0.029(2) Uani 1 1 d . . . . .
C14 C 0.6427(5) -0.1483(4) 0.0866(7) 0.027(2) Uani 1 1 d . . . . .
H14 H 0.657632 -0.143416 0.013913 0.033 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C7 1.737(8) . ?
S1 C1 1.743(8) . ?
S2 C11 1.731(7) . ?
S2 C17 1.750(9) . ?
S3 C21 1.739(7) . ?
S3 C27 1.742(9) . ?
S4 C29 1.737(7) . ?
S4 C35 1.743(8) . ?
F1 C8 1.329(10) . ?
F2 C8 1.335(9) . ?
F3 C8 1.319(11) . ?
F4 C18 1.321(10) . ?
F5 C18 1.348(10) . ?
F6 C18 1.342(10) . ?
F7 C28 1.351(11) . ?
F8 C28 1.335(10) . ?
F9 C28 1.330(10) . ?
F10 C36 1.329(10) . ?
F11 C36 1.329(10) . ?
F12 C36 1.327(11) . ?
O1 C8 1.345(10) . ?
O1 C5 1.417(9) . ?
O2 C9 1.247(9) . ?
O3 C9 1.272(9) . ?
O3 H6 1.37(8) . ?
O4 C10 1.255(9) . ?
O5 C10 1.254(9) . ?
O6 C18 1.329(11) . ?
O6 C15 1.427(10) . ?
O7 C19 1.241(9) . ?
O8 C19 1.272(9) . ?
O8 H4 1.47(10) . ?
O9 C20 1.258(9) . ?
O10 C20 1.254(9) . ?
O11 C28 1.303(11) . ?
O11 C25 1.429(9) . ?
O12 C36 1.314(11) . ?
O12 C33 1.411(9) . ?
N1 C1 1.312(11) . ?
N1 H1A 0.90(9) . ?
N1 H1B 0.89(9) . ?
N2 C1 1.329(10) . ?
N2 C2 1.388(10) . ?
N2 H2 0.90(8) . ?
N3 C11 1.302(10) . ?
N3 H3A 0.98(9) . ?
N3 H3B 0.85(8) . ?
N4 C11 1.339(9) . ?
N4 C12 1.365(11) . ?
N4 H4 1.12(10) . ?
N5 C21 1.282(10) . ?
N5 H5A 0.91(9) . ?
N5 H5B 0.88(8) . ?
N6 C21 1.340(9) . ?
N6 C22 1.387(10) . ?
N6 H6 1.26(8) . ?
N7 C29 1.309(10) . ?
N7 H7A 0.77(8) . ?
N7 H7B 0.95(8) . ?
N8 C29 1.350(10) . ?
N8 C30 1.379(10) . ?
N8 H8 0.80(8) . ?
C2 C7 1.388(10) . ?
C2 C3 1.389(11) . ?
C5 C6 1.380(11) . ?
C5 C4 1.382(11) . ?
C6 C7 1.400(10) . ?
C6 H6A 0.9500 . ?
C12 C17 1.386(10) . ?
C12 C13 1.401(11) . ?
C35 C34 1.390(11) . ?
C35 C30 1.391(10) . ?
C22 C23 1.373(11) . ?
C22 C27 1.405(10) . ?
C9 C10 1.543(10) . ?
C26 C27 1.371(11) . ?
C26 C25 1.382(12) . ?
C26 H26 0.9500 . ?
C4 C3 1.379(11) . ?
C4 H4A 0.9500 . ?
C34 C33 1.390(11) . ?
C34 H34 0.9500 . ?
C13 C14 1.350(12) . ?
C13 H13 0.9500 . ?
C33 C32 1.380(11) . ?
C23 C24 1.387(11) . ?
C23 H23 0.9500 . ?
C20 C19 1.558(10) . ?
C32 C31 1.378(11) . ?
C32 H32 0.9500 . ?
C3 H3 0.9500 . ?
C16 C15 1.368(12) . ?
C16 C17 1.391(11) . ?
C16 H16 0.9500 . ?
C30 C31 1.391(11) . ?
C31 H31 0.9500 . ?
C25 C24 1.386(11) . ?
C15 C14 1.387(12) . ?
C24 H24 0.9500 . ?
C14 H14 0.9500 . ?

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
C7 S1 C1 89.9(4) . . ?
C11 S2 C17 89.4(4) . . ?
C21 S3 C27 90.2(4) . . ?
C29 S4 C35 90.4(4) . . ?
C8 O1 C5 120.0(7) . . ?
C9 O3 H6 118(3) . . ?
C18 O6 C15 116.7(6) . . ?
C19 O8 H4 119(4) . . ?
C28 O11 C25 117.7(7) . . ?
C36 O12 C33 116.3(6) . . ?
C1 N1 H1A 118(6) . . ?
C1 N1 H1B 121(6) . . ?
H1A N1 H1B 121(8) . . ?
C1 N2 C2 114.2(7) . . ?
C1 N2 H2 119(5) . . ?
C2 N2 H2 127(5) . . ?
C11 N3 H3A 122(5) . . ?
C11 N3 H3B 118(6) . . ?
H3A N3 H3B 120(8) . . ?
C11 N4 C12 112.9(6) . . ?
C11 N4 H4 124(5) . . ?
C12 N4 H4 122(5) . . ?
C21 N5 H5A 118(5) . . ?
C21 N5 H5B 121(6) . . ?
H5A N5 H5B 119(8) . . ?
C21 N6 C22 114.1(6) . . ?
C21 N6 H6 119(4) . . ?
C22 N6 H6 126(4) . . ?
C29 N7 H7A 118(7) . . ?
C29 N7 H7B 126(5) . . ?
H7A N7 H7B 116(9) . . ?
C29 N8 C30 114.0(6) . . ?
C29 N8 H8 110(6) . . ?
C30 N8 H8 136(6) . . ?
N1 C1 N2 124.1(7) . . ?
N1 C1 S1 123.6(6) . . ?
N2 C1 S1 112.3(6) . . ?
C7 C2 N2 112.1(7) . . ?
C7 C2 C3 120.0(7) . . ?
N2 C2 C3 127.9(7) . . ?
C6 C5 C4 123.3(8) . . ?
C6 C5 O1 123.0(7) . . ?
C4 C5 O1 113.6(7) . . ?
C5 C6 C7 115.3(7) . . ?
C5 C6 H6A 122.3 . . ?
C7 C6 H6A 122.3 . . ?
N4 C12 C17 113.9(7) . . ?
N4 C12 C13 126.5(7) . . ?
C17 C12 C13 119.6(8) . . ?
C34 C35 C30 122.7(7) . . ?
C34 C35 S4 126.7(6) . . ?
C30 C35 S4 110.6(6) . . ?
N7 C29 N8 124.1(7) . . ?
N7 C29 S4 124.0(6) . . ?
N8 C29 S4 111.9(6) . . ?
C23 C22 N6 126.7(7) . . ?
C23 C22 C27 121.1(7) . . ?
N6 C22 C27 112.2(7) . . ?
C2 C7 C6 122.5(7) . . ?
C2 C7 S1 111.2(6) . . ?
C6 C7 S1 126.2(6) . . ?
N5 C21 N6 124.1(6) . . ?
N5 C21 S3 123.2(6) . . ?
N6 C21 S3 112.7(6) . . ?
O2 C9 O3 125.5(7) . . ?
O2 C9 C10 117.8(6) . . ?
O3 C9 C10 116.7(6) . . ?
C27 C26 C25 116.4(7) . . ?
C27 C26 H26 121.8 . . ?
C25 C26 H26 121.8 . . ?
C3 C4 C5 120.3(8) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
C35 C34 C33 115.9(7) . . ?
C35 C34 H34 122.1 . . ?
C33 C34 H34 122.1 . . ?
C14 C13 C12 119.6(8) . . ?
C14 C13 H13 120.2 . . ?
C12 C13 H13 120.2 . . ?
O5 C10 O4 126.0(7) . . ?
O5 C10 C9 116.5(6) . . ?
O4 C10 C9 117.4(6) . . ?
O11 C28 F9 109.0(7) . . ?
O11 C28 F8 115.5(8) . . ?
F9 C28 F8 106.9(8) . . ?
O11 C28 F7 113.5(8) . . ?
F9 C28 F7 106.3(8) . . ?
F8 C28 F7 105.1(7) . . ?
F4 C18 O6 113.8(8) . . ?
F4 C18 F6 107.1(7) . . ?
O6 C18 F6 113.4(8) . . ?
F4 C18 F5 107.7(8) . . ?
O6 C18 F5 107.2(7) . . ?
F6 C18 F5 107.5(8) . . ?
C32 C33 C34 122.3(8) . . ?
C32 C33 O12 121.1(8) . . ?
C34 C33 O12 116.4(7) . . ?
C22 C23 C24 118.3(8) . . ?
C22 C23 H23 120.9 . . ?
C24 C23 H23 120.9 . . ?
O10 C20 O9 126.0(7) . . ?
O10 C20 C19 117.0(6) . . ?
O9 C20 C19 117.0(6) . . ?
C31 C32 C33 120.9(8) . . ?
C31 C32 H32 119.6 . . ?
C33 C32 H32 119.6 . . ?
C4 C3 C2 118.4(7) . . ?
C4 C3 H3 120.8 . . ?
C2 C3 H3 120.8 . . ?
C15 C16 C17 116.1(8) . . ?
C15 C16 H16 121.9 . . ?
C17 C16 H16 121.9 . . ?
N8 C30 C31 127.4(7) . . ?
N8 C30 C35 112.9(7) . . ?
C31 C30 C35 119.7(7) . . ?
N3 C11 N4 122.7(6) . . ?
N3 C11 S2 124.0(6) . . ?
N4 C11 S2 113.4(6) . . ?
C32 C31 C30 118.5(7) . . ?
C32 C31 H31 120.7 . . ?
C30 C31 H31 120.7 . . ?
C26 C25 C24 123.6(8) . . ?
C26 C25 O11 116.3(7) . . ?
C24 C25 O11 119.8(7) . . ?
C16 C15 C14 123.7(8) . . ?
C16 C15 O6 116.6(8) . . ?
C14 C15 O6 119.7(8) . . ?
O7 C19 O8 125.8(7) . . ?
O7 C19 C20 118.2(6) . . ?
O8 C19 C20 116.0(6) . . ?
C12 C17 C16 121.6(8) . . ?
C12 C17 S2 110.2(6) . . ?
C16 C17 S2 128.1(7) . . ?
O12 C36 F12 114.0(8) . . ?
O12 C36 F11 113.9(8) . . ?
F12 C36 F11 105.7(8) . . ?
O12 C36 F10 107.6(7) . . ?
F12 C36 F10 107.8(8) . . ?
F11 C36 F10 107.5(8) . . ?
C26 C27 C22 121.3(8) . . ?
C26 C27 S3 127.7(6) . . ?
C22 C27 S3 110.8(6) . . ?
C25 C24 C23 119.3(8) . . ?
C25 C24 H24 120.4 . . ?
C23 C24 H24 120.4 . . ?
F3 C8 F1 109.1(7) . . ?
F3 C8 F2 108.0(7) . . ?
F1 C8 F2 107.2(7) . . ?
F3 C8 O1 113.9(7) . . ?
F1 C8 O1 106.2(7) . . ?
F2 C8 O1 112.3(7) . . ?
C13 C14 C15 119.3(8) . . ?
C13 C14 H14 120.4 . . ?
C15 C14 H14 120.4 . . ?

_refine_diff_density_max         0.513
_refine_diff_density_min         -0.504
_refine_diff_density_rms         0.108

####################################################################### 
# 
# 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_RZ-OA-170K
_database_code_depnum_ccdc_archive 'CCDC 1572078'
_audit_update_record             
;
2017-11-20 deposited with the CCDC.
2018-03-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H12 F6 N4 O6 S2'
_chemical_formula_weight         558.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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'

_cell_length_a                   18.9397(12)
_cell_length_b                   20.1917(12)
_cell_length_c                   11.7038(7)
_cell_angle_alpha                90
_cell_angle_beta                 101.450(3)
_cell_angle_gamma                90
_cell_volume                     4386.7(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    170(2)
_cell_measurement_reflns_used    9978
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      29.84

_exptl_crystal_description       Plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.691
_exptl_crystal_F_000             2256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.339
_shelx_estimated_absorpt_T_min   0.862
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_process_details   'SADABS 2014/4'
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.8460
_exptl_absorpt_correction_T_min  0.6119
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      170(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            46121
_diffrn_reflns_av_unetI/netI     0.0564
_diffrn_reflns_av_R_equivalents  0.0517
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.490
_diffrn_reflns_theta_max         30.247
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_point_group_measured_fraction_full 0.958
_reflns_number_total             12083
_reflns_number_gt                9293
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.852
_reflns_Friedel_fraction_max     0.850
_reflns_Friedel_fraction_full    0.916

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0709P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_chemical_absolute_configuration ?
_refine_ls_number_reflns         12083
_refine_ls_number_parameters     697
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0485
_refine_ls_wR_factor_ref         0.1336
_refine_ls_wR_factor_gt          0.1192
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.40830(6) 0.16192(5) 0.88200(8) 0.0314(2) Uani 1 1 d . . . . .
F1 F 0.62443(17) 0.19942(17) 0.5184(3) 0.0610(8) Uani 1 1 d . . . . .
F2 F 0.63867(17) 0.24887(15) 0.6829(3) 0.0509(7) Uani 1 1 d . . . . .
F3 F 0.62923(18) 0.30534(18) 0.5263(3) 0.0701(10) Uani 1 1 d . . . . .
O1 O 0.53420(18) 0.25859(17) 0.5612(3) 0.0485(9) Uani 1 1 d . . . . .
N1 N 0.3412(2) 0.04670(17) 0.9113(3) 0.0298(8) Uani 1 1 d . . . . .
H1A H 0.332(3) 0.001(3) 0.890(4) 0.038(13) Uiso 1 1 d . . . . .
H1B H 0.342(2) 0.059(2) 0.969(4) 0.023(12) Uiso 1 1 d . . . . .
N2 N 0.38396(19) 0.06336(16) 0.7408(3) 0.0248(7) Uani 1 1 d . . . . .
H2 H 0.358(4) 0.023(3) 0.706(6) 0.08(2) Uiso 1 1 d . . . . .
C1 C 0.3737(2) 0.08285(17) 0.8445(3) 0.0231(7) Uani 1 1 d . . . . .
C2 C 0.4220(2) 0.10841(19) 0.6871(3) 0.0255(8) Uani 1 1 d . . . . .
C3 C 0.4415(3) 0.0998(2) 0.5792(3) 0.0345(9) Uani 1 1 d . . . . .
H3 H 0.428970 0.060690 0.534654 0.041 Uiso 1 1 calc R U . . .
C4 C 0.4797(3) 0.1502(3) 0.5394(4) 0.0401(11) Uani 1 1 d . . . . .
H4A H 0.493557 0.146235 0.466079 0.048 Uiso 1 1 calc R U . . .
C5 C 0.4977(2) 0.2062(2) 0.6059(4) 0.0374(10) Uani 1 1 d . . . . .
C6 C 0.4786(2) 0.2161(2) 0.7115(4) 0.0361(9) Uani 1 1 d . . . . .
H6A H 0.490809 0.255746 0.754732 0.043 Uiso 1 1 calc R U . . .
C7 C 0.4404(2) 0.1655(2) 0.7527(3) 0.0279(8) Uani 1 1 d . . . . .
C8 C 0.6055(3) 0.2523(3) 0.5728(5) 0.0467(12) Uani 1 1 d . . . . .
S2 S 0.26486(6) 0.42329(5) 0.00540(8) 0.0281(2) Uani 1 1 d . . . . .
F4 F 0.0342(2) 0.4979(3) 0.3366(5) 0.1021(15) Uani 1 1 d . . . . .
F5 F 0.0335(2) 0.5261(2) 0.1661(4) 0.0898(14) Uani 1 1 d . . . . .
F6 F 0.0393(2) 0.6009(2) 0.2957(4) 0.0829(12) Uani 1 1 d . . . . .
O10 O 0.13343(18) 0.54070(17) 0.2982(3) 0.0453(9) Uani 1 1 d . . . . .
N3 N 0.31614(19) 0.30115(16) -0.0192(3) 0.0273(7) Uani 1 1 d . . . . .
H3A H 0.326(3) 0.259(2) 0.008(4) 0.033(12) Uiso 1 1 d . . . . .
H3B H 0.330(3) 0.322(3) -0.099(4) 0.045(14) Uiso 1 1 d . . . . .
N4 N 0.27569(18) 0.32740(16) 0.1513(3) 0.0242(7) Uani 1 1 d . . . . .
H4 H 0.291(3) 0.287(3) 0.178(4) 0.037(13) Uiso 1 1 d . . . . .
C13 C 0.2887(2) 0.34260(18) 0.0459(3) 0.0217(7) Uani 1 1 d . . . . .
C14 C 0.2401(2) 0.37721(19) 0.1998(3) 0.0241(7) Uani 1 1 d . . . . .
C15 C 0.2159(3) 0.3746(2) 0.3038(3) 0.0347(10) Uani 1 1 d . . . . .
H15 H 0.224144 0.336602 0.352570 0.042 Uiso 1 1 calc R U . . .
C16 C 0.1790(3) 0.4293(2) 0.3347(4) 0.0378(10) Uani 1 1 d . . . . .
H16 H 0.161100 0.428732 0.405001 0.045 Uiso 1 1 calc R U . . .
C17 C 0.1684(2) 0.4845(2) 0.2630(4) 0.0339(9) Uani 1 1 d . . . . .
C18 C 0.1938(2) 0.4888(2) 0.1618(4) 0.0322(9) Uani 1 1 d . . . . .
H18 H 0.187312 0.527595 0.115003 0.039 Uiso 1 1 calc R U . . .
C19 C 0.2296(2) 0.4338(2) 0.1309(3) 0.0257(8) Uani 1 1 d . . . . .
C20 C 0.0618(3) 0.5407(3) 0.2740(6) 0.0603(16) Uani 1 1 d . . . . .
S3 S 0.23405(6) 0.08886(5) 0.49493(8) 0.0295(2) Uani 1 1 d . . . . .
F7 F 0.1265(2) -0.10302(14) 0.7244(3) 0.0623(9) Uani 1 1 d . . . . .
F8 F 0.0337(2) -0.09916(19) 0.8017(3) 0.0760(11) Uani 1 1 d . . . . .
F9 F 0.03228(19) -0.0531(2) 0.6365(3) 0.0776(11) Uani 1 1 d . . . . .
O11 O 0.0947(2) -0.01073(17) 0.8017(3) 0.0493(9) Uani 1 1 d . . . . .
N5 N 0.3006(2) 0.20472(18) 0.4741(3) 0.0279(7) Uani 1 1 d . . . . .
H5A H 0.309(3) 0.242(3) 0.495(4) 0.030(12) Uiso 1 1 d . . . . .
H5B H 0.309(3) 0.186(3) 0.400(5) 0.045(14) Uiso 1 1 d . . . . .
N6 N 0.25778(18) 0.18343(16) 0.6439(3) 0.0240(6) Uani 1 1 d . . . . .
H6 H 0.276(3) 0.223(3) 0.671(5) 0.050(15) Uiso 1 1 d . . . . .
C21 C 0.2686(2) 0.16625(17) 0.5381(3) 0.0232(8) Uani 1 1 d . . . . .
C22 C 0.2175(2) 0.13738(19) 0.6929(3) 0.0253(8) Uani 1 1 d . . . . .
C23 C 0.1946(2) 0.1424(2) 0.7978(3) 0.0322(9) Uani 1 1 d . . . . .
H23 H 0.206558 0.179919 0.846833 0.039 Uiso 1 1 calc R U . . .
C24 C 0.1536(3) 0.0910(2) 0.8291(4) 0.0358(10) Uani 1 1 d . . . . .
H24 H 0.136605 0.093434 0.900075 0.043 Uiso 1 1 calc R U . . .
C25 C 0.1375(2) 0.0367(2) 0.7581(4) 0.0338(9) Uani 1 1 d . . . . .
C26 C 0.1600(2) 0.0302(2) 0.6535(4) 0.0345(10) Uani 1 1 d . . . . .
H26 H 0.148748 -0.007868 0.605609 0.041 Uiso 1 1 calc R U . . .
C27 C 0.1999(2) 0.08214(19) 0.6225(3) 0.0265(8) Uani 1 1 d . . . . .
C28 C 0.0721(3) -0.0649(3) 0.7412(5) 0.0504(13) Uani 1 1 d . . . . .
S4 S 0.42410(6) 0.33651(5) 0.39290(8) 0.0324(3) Uani 1 1 d . . . . .
F10 F 0.6284(2) 0.2486(2) 0.0118(3) 0.0764(11) Uani 1 1 d . . . . .
F11 F 0.63928(18) 0.21546(18) 0.1883(3) 0.0695(10) Uani 1 1 d . . . . .
F12 F 0.6118(2) 0.14660(19) 0.0483(4) 0.0841(12) Uani 1 1 d . . . . .
O12 O 0.53152(18) 0.21628(17) 0.0755(3) 0.0472(9) Uani 1 1 d . . . . .
N7 N 0.3733(2) 0.45836(17) 0.4223(3) 0.0285(7) Uani 1 1 d . . . . .
H7A H 0.363(2) 0.449(2) 0.482(4) 0.024(11) Uiso 1 1 d . . . . .
H7B H 0.361(3) 0.503(3) 0.398(4) 0.047(15) Uiso 1 1 d . . . . .
N8 N 0.41822(18) 0.43637(16) 0.2547(2) 0.0245(6) Uani 1 1 d . . . . .
H8 H 0.396(3) 0.485(3) 0.213(5) 0.053(16) Uiso 1 1 d . . . . .
C29 C 0.4023(2) 0.41845(17) 0.3567(3) 0.0233(8) Uani 1 1 d . . . . .
C30 C 0.4507(2) 0.38629(18) 0.2020(3) 0.0229(7) Uani 1 1 d . . . . .
C31 C 0.4733(2) 0.3894(2) 0.0959(3) 0.0298(9) Uani 1 1 d . . . . .
H31 H 0.468812 0.429342 0.052188 0.036 Uiso 1 1 calc R U . . .
C32 C 0.5023(3) 0.3337(2) 0.0555(4) 0.0367(10) Uani 1 1 d . . . . .
H32 H 0.517809 0.334728 -0.016788 0.044 Uiso 1 1 calc R U . . .
C33 C 0.5086(2) 0.2760(2) 0.1210(4) 0.0348(9) Uani 1 1 d . . . . .
C34 C 0.4869(2) 0.2710(2) 0.2259(4) 0.0336(9) Uani 1 1 d . . . . .
H34 H 0.491392 0.230777 0.268915 0.040 Uiso 1 1 calc R U . . .
C35 C 0.4582(2) 0.3276(2) 0.2658(3) 0.0286(8) Uani 1 1 d . . . . .
C36 C 0.6005(3) 0.2075(3) 0.0821(6) 0.0559(15) Uani 1 1 d . . . . .
O2 O 0.3349(2) 0.04778(13) 0.1470(2) 0.0401(8) Uani 1 1 d . . . . .
O3 O 0.3254(2) 0.08472(13) 0.3222(2) 0.0355(7) Uani 1 1 d . . . . .
O4 O 0.3188(2) 0.17100(13) 0.0624(2) 0.0383(8) Uani 1 1 d . . . . .
O5 O 0.31090(18) 0.20929(13) 0.2386(2) 0.0337(7) Uani 1 1 d . . . . .
C9 C 0.3271(2) 0.09276(18) 0.2185(3) 0.0260(8) Uani 1 1 d . . . . .
C10 C 0.3180(2) 0.16434(18) 0.1679(3) 0.0253(8) Uani 1 1 d . . . . .
O6 O 0.3250(2) 0.33378(13) 0.5630(2) 0.0371(7) Uani 1 1 d . . . . .
O7 O 0.31373(17) 0.29511(12) 0.7376(2) 0.0299(6) Uani 1 1 d . . . . .
O8 O 0.35671(18) 0.41265(13) 0.8331(2) 0.0328(7) Uani 1 1 d . . . . .
O9 O 0.36880(17) 0.45129(13) 0.6592(2) 0.0311(7) Uani 1 1 d . . . . .
C11 C 0.3290(2) 0.33896(18) 0.6699(3) 0.0241(8) Uani 1 1 d . . . . .
C12 C 0.3534(2) 0.40689(18) 0.7268(3) 0.0223(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C7 1.740(4) . ?
S1 C1 1.748(4) . ?
F1 C8 1.327(6) . ?
F2 C8 1.318(6) . ?
F3 C8 1.320(5) . ?
O1 C8 1.337(6) . ?
O1 C5 1.419(5) . ?
N1 C1 1.309(5) . ?
N1 H1A 0.96(6) . ?
N1 H1B 0.72(4) . ?
N2 C1 1.326(4) . ?
N2 C2 1.386(5) . ?
N2 H2 1.01(7) . ?
C2 C7 1.390(6) . ?
C2 C3 1.396(5) . ?
C3 C4 1.382(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.376(7) . ?
C4 H4A 0.9500 . ?
C5 C6 1.370(6) . ?
C6 C7 1.393(6) . ?
C6 H6A 0.9500 . ?
S2 C13 1.731(4) . ?
S2 C19 1.743(4) . ?
F4 C20 1.307(8) . ?
F5 C20 1.304(8) . ?
F6 C20 1.328(7) . ?
O10 C20 1.329(7) . ?
O10 C17 1.416(5) . ?
N3 C13 1.307(5) . ?
N3 H3A 0.92(5) . ?
N3 H3B 1.11(5) . ?
N4 C13 1.340(4) . ?
N4 C14 1.393(5) . ?
N4 H4 0.90(5) . ?
C14 C15 1.384(5) . ?
C14 C19 1.391(5) . ?
C15 C16 1.392(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(7) . ?
C16 H16 0.9500 . ?
C17 C18 1.368(6) . ?
C18 C19 1.385(6) . ?
C18 H18 0.9500 . ?
S3 C21 1.730(4) . ?
S3 C27 1.746(4) . ?
F7 C28 1.333(7) . ?
F8 C28 1.309(6) . ?
F9 C28 1.327(6) . ?
O11 C28 1.326(6) . ?
O11 C25 1.413(5) . ?
N5 C21 1.309(5) . ?
N5 H5A 0.79(5) . ?
N5 H5B 0.99(5) . ?
N6 C21 1.340(4) . ?
N6 C22 1.396(5) . ?
N6 H6 0.90(6) . ?
C22 C23 1.385(5) . ?
C22 C27 1.388(5) . ?
C23 C24 1.388(6) . ?
C23 H23 0.9500 . ?
C24 C25 1.373(6) . ?
C24 H24 0.9500 . ?
C25 C26 1.380(6) . ?
C26 C27 1.383(6) . ?
C26 H26 0.9500 . ?
S4 C29 1.737(4) . ?
S4 C35 1.744(4) . ?
F10 C36 1.348(7) . ?
F11 C36 1.321(7) . ?
F12 C36 1.322(6) . ?
O12 C36 1.305(6) . ?
O12 C33 1.420(5) . ?
N7 C29 1.308(5) . ?
N7 H7A 0.79(4) . ?
N7 H7B 0.96(6) . ?
N8 C29 1.337(4) . ?
N8 C30 1.390(5) . ?
N8 H8 1.14(6) . ?
C30 C35 1.392(5) . ?
C30 C31 1.393(5) . ?
C31 C32 1.376(6) . ?
C31 H31 0.9500 . ?
C32 C33 1.386(7) . ?
C32 H32 0.9500 . ?
C33 C34 1.373(6) . ?
C34 C35 1.387(6) . ?
C34 H34 0.9500 . ?
O2 C9 1.264(4) . ?
O3 C9 1.232(4) . ?
O4 C10 1.245(4) . ?
O5 C10 1.253(4) . ?
C9 C10 1.558(5) . ?
O6 C11 1.243(4) . ?
O7 C11 1.259(4) . ?
O8 C12 1.239(4) . ?
O9 C12 1.268(4) . ?
C11 C12 1.555(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
C7 S1 C1 89.83(18) . . ?
C8 O1 C5 116.7(3) . . ?
C1 N1 H1A 118(3) . . ?
C1 N1 H1B 116(4) . . ?
H1A N1 H1B 124(5) . . ?
C1 N2 C2 113.8(3) . . ?
C1 N2 H2 118(4) . . ?
C2 N2 H2 128(4) . . ?
N1 C1 N2 123.5(3) . . ?
N1 C1 S1 123.8(3) . . ?
N2 C1 S1 112.7(3) . . ?
N2 C2 C7 112.9(3) . . ?
N2 C2 C3 125.7(4) . . ?
C7 C2 C3 121.4(4) . . ?
C4 C3 C2 117.6(4) . . ?
C4 C3 H3 121.2 . . ?
C2 C3 H3 121.2 . . ?
C5 C4 C3 120.1(4) . . ?
C5 C4 H4A 119.9 . . ?
C3 C4 H4A 119.9 . . ?
C6 C5 C4 123.4(4) . . ?
C6 C5 O1 117.3(4) . . ?
C4 C5 O1 119.2(4) . . ?
C5 C6 C7 116.9(4) . . ?
C5 C6 H6A 121.5 . . ?
C7 C6 H6A 121.5 . . ?
C2 C7 C6 120.5(4) . . ?
C2 C7 S1 110.7(3) . . ?
C6 C7 S1 128.7(3) . . ?
F2 C8 F3 108.1(5) . . ?
F2 C8 F1 107.8(4) . . ?
F3 C8 F1 108.0(4) . . ?
F2 C8 O1 112.3(4) . . ?
F3 C8 O1 107.5(4) . . ?
F1 C8 O1 113.1(5) . . ?
C13 S2 C19 90.38(18) . . ?
C20 O10 C17 117.0(4) . . ?
C13 N3 H3A 118(3) . . ?
C13 N3 H3B 116(3) . . ?
H3A N3 H3B 126(4) . . ?
C13 N4 C14 113.7(3) . . ?
C13 N4 H4 115(3) . . ?
C14 N4 H4 131(3) . . ?
N3 C13 N4 123.8(3) . . ?
N3 C13 S2 123.7(3) . . ?
N4 C13 S2 112.5(3) . . ?
C15 C14 C19 120.5(4) . . ?
C15 C14 N4 127.0(4) . . ?
C19 C14 N4 112.4(3) . . ?
C14 C15 C16 118.0(4) . . ?
C14 C15 H15 121.0 . . ?
C16 C15 H15 121.0 . . ?
C17 C16 C15 120.1(4) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C18 C17 C16 122.8(4) . . ?
C18 C17 O10 117.8(4) . . ?
C16 C17 O10 119.3(4) . . ?
C17 C18 C19 116.7(4) . . ?
C17 C18 H18 121.6 . . ?
C19 C18 H18 121.6 . . ?
C18 C19 C14 121.9(4) . . ?
C18 C19 S2 127.4(3) . . ?
C14 C19 S2 110.7(3) . . ?
F5 C20 F4 105.1(6) . . ?
F5 C20 F6 107.8(6) . . ?
F4 C20 F6 108.6(5) . . ?
F5 C20 O10 114.3(5) . . ?
F4 C20 O10 112.6(6) . . ?
F6 C20 O10 108.2(5) . . ?
C21 S3 C27 90.21(18) . . ?
C28 O11 C25 120.9(4) . . ?
C21 N5 H5A 118(4) . . ?
C21 N5 H5B 117(3) . . ?
H5A N5 H5B 126(5) . . ?
C21 N6 C22 113.8(3) . . ?
C21 N6 H6 116(4) . . ?
C22 N6 H6 131(4) . . ?
N5 C21 N6 123.2(3) . . ?
N5 C21 S3 124.1(3) . . ?
N6 C21 S3 112.7(3) . . ?
C23 C22 C27 120.3(4) . . ?
C23 C22 N6 127.5(4) . . ?
C27 C22 N6 112.2(3) . . ?
C22 C23 C24 118.0(4) . . ?
C22 C23 H23 121.0 . . ?
C24 C23 H23 121.0 . . ?
C25 C24 C23 120.4(4) . . ?
C25 C24 H24 119.8 . . ?
C23 C24 H24 119.8 . . ?
C24 C25 C26 122.9(4) . . ?
C24 C25 O11 113.4(4) . . ?
C26 C25 O11 123.7(4) . . ?
C25 C26 C27 116.2(4) . . ?
C25 C26 H26 121.9 . . ?
C27 C26 H26 121.9 . . ?
C26 C27 C22 122.2(3) . . ?
C26 C27 S3 126.7(3) . . ?
C22 C27 S3 111.0(3) . . ?
F8 C28 O11 107.7(5) . . ?
F8 C28 F9 108.7(5) . . ?
O11 C28 F9 114.2(5) . . ?
F8 C28 F7 107.6(4) . . ?
O11 C28 F7 112.1(5) . . ?
F9 C28 F7 106.4(5) . . ?
C29 S4 C35 89.98(18) . . ?
C36 O12 C33 118.0(4) . . ?
C29 N7 H7A 125(3) . . ?
C29 N7 H7B 120(3) . . ?
H7A N7 H7B 115(4) . . ?
C29 N8 C30 113.4(3) . . ?
C29 N8 H8 119(3) . . ?
C30 N8 H8 127(3) . . ?
N7 C29 N8 123.6(3) . . ?
N7 C29 S4 123.4(3) . . ?
N8 C29 S4 113.0(3) . . ?
N8 C30 C35 112.8(3) . . ?
N8 C30 C31 127.2(3) . . ?
C35 C30 C31 120.0(3) . . ?
C32 C31 C30 118.9(4) . . ?
C32 C31 H31 120.5 . . ?
C30 C31 H31 120.5 . . ?
C31 C32 C33 119.6(4) . . ?
C31 C32 H32 120.2 . . ?
C33 C32 H32 120.2 . . ?
C34 C33 C32 123.2(4) . . ?
C34 C33 O12 116.1(4) . . ?
C32 C33 O12 120.4(4) . . ?
C33 C34 C35 116.6(4) . . ?
C33 C34 H34 121.7 . . ?
C35 C34 H34 121.7 . . ?
C34 C35 C30 121.7(4) . . ?
C34 C35 S4 127.5(3) . . ?
C30 C35 S4 110.8(3) . . ?
O12 C36 F11 113.7(5) . . ?
O12 C36 F12 109.2(4) . . ?
F11 C36 F12 107.6(5) . . ?
O12 C36 F10 112.9(5) . . ?
F11 C36 F10 106.6(5) . . ?
F12 C36 F10 106.5(5) . . ?
O3 C9 O2 126.0(3) . . ?
O3 C9 C10 118.3(3) . . ?
O2 C9 C10 115.7(3) . . ?
O4 C10 O5 126.9(3) . . ?
O4 C10 C9 117.0(3) . . ?
O5 C10 C9 116.0(3) . . ?
O6 C11 O7 126.8(3) . . ?
O6 C11 C12 117.3(3) . . ?
O7 C11 C12 115.9(3) . . ?
O8 C12 O9 126.1(3) . . ?
O8 C12 C11 117.7(3) . . ?
O9 C12 C11 116.2(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N2 C1 N1 -177.6(4) . . . . ?
C2 N2 C1 S1 2.3(4) . . . . ?
C7 S1 C1 N1 177.7(4) . . . . ?
C7 S1 C1 N2 -2.3(3) . . . . ?
C1 N2 C2 C7 -1.1(5) . . . . ?
C1 N2 C2 C3 178.5(4) . . . . ?
N2 C2 C3 C4 -179.8(4) . . . . ?
C7 C2 C3 C4 -0.2(6) . . . . ?
C2 C3 C4 C5 0.5(7) . . . . ?
C3 C4 C5 C6 -1.2(7) . . . . ?
C3 C4 C5 O1 -177.3(4) . . . . ?
C8 O1 C5 C6 101.6(5) . . . . ?
C8 O1 C5 C4 -82.0(6) . . . . ?
C4 C5 C6 C7 1.4(7) . . . . ?
O1 C5 C6 C7 177.7(4) . . . . ?
N2 C2 C7 C6 -179.8(4) . . . . ?
C3 C2 C7 C6 0.5(6) . . . . ?
N2 C2 C7 S1 -0.7(5) . . . . ?
C3 C2 C7 S1 179.7(3) . . . . ?
C5 C6 C7 C2 -1.1(6) . . . . ?
C5 C6 C7 S1 179.9(3) . . . . ?
C1 S1 C7 C2 1.6(3) . . . . ?
C1 S1 C7 C6 -179.3(4) . . . . ?
C5 O1 C8 F2 -61.3(6) . . . . ?
C5 O1 C8 F3 180.0(4) . . . . ?
C5 O1 C8 F1 60.9(6) . . . . ?
C14 N4 C13 N3 -174.3(4) . . . . ?
C14 N4 C13 S2 5.6(4) . . . . ?
C19 S2 C13 N3 175.3(4) . . . . ?
C19 S2 C13 N4 -4.6(3) . . . . ?
C13 N4 C14 C15 176.0(4) . . . . ?
C13 N4 C14 C19 -3.7(5) . . . . ?
C19 C14 C15 C16 2.0(6) . . . . ?
N4 C14 C15 C16 -177.7(4) . . . . ?
C14 C15 C16 C17 -0.9(7) . . . . ?
C15 C16 C17 C18 -1.2(7) . . . . ?
C15 C16 C17 O10 -177.4(4) . . . . ?
C20 O10 C17 C18 99.1(6) . . . . ?
C20 O10 C17 C16 -84.6(6) . . . . ?
C16 C17 C18 C19 2.0(6) . . . . ?
O10 C17 C18 C19 178.2(4) . . . . ?
C17 C18 C19 C14 -0.8(6) . . . . ?
C17 C18 C19 S2 177.4(3) . . . . ?
C15 C14 C19 C18 -1.2(6) . . . . ?
N4 C14 C19 C18 178.5(4) . . . . ?
C15 C14 C19 S2 -179.7(3) . . . . ?
N4 C14 C19 S2 0.1(4) . . . . ?
C13 S2 C19 C18 -175.8(4) . . . . ?
C13 S2 C19 C14 2.5(3) . . . . ?
C17 O10 C20 F5 -49.8(8) . . . . ?
C17 O10 C20 F4 70.1(6) . . . . ?
C17 O10 C20 F6 -169.9(5) . . . . ?
C22 N6 C21 N5 175.1(4) . . . . ?
C22 N6 C21 S3 -3.7(4) . . . . ?
C27 S3 C21 N5 -175.8(4) . . . . ?
C27 S3 C21 N6 3.0(3) . . . . ?
C21 N6 C22 C23 -176.6(4) . . . . ?
C21 N6 C22 C27 2.5(5) . . . . ?
C27 C22 C23 C24 -0.3(6) . . . . ?
N6 C22 C23 C24 178.7(4) . . . . ?
C22 C23 C24 C25 0.9(7) . . . . ?
C23 C24 C25 C26 -0.5(7) . . . . ?
C23 C24 C25 O11 -179.3(4) . . . . ?
C28 O11 C25 C24 177.3(5) . . . . ?
C28 O11 C25 C26 -1.6(7) . . . . ?
C24 C25 C26 C27 -0.5(7) . . . . ?
O11 C25 C26 C27 178.2(4) . . . . ?
C25 C26 C27 C22 1.1(6) . . . . ?
C25 C26 C27 S3 -178.6(3) . . . . ?
C23 C22 C27 C26 -0.7(6) . . . . ?
N6 C22 C27 C26 -179.9(4) . . . . ?
C23 C22 C27 S3 179.1(3) . . . . ?
N6 C22 C27 S3 -0.1(4) . . . . ?
C21 S3 C27 C26 178.2(4) . . . . ?
C21 S3 C27 C22 -1.6(3) . . . . ?
C25 O11 C28 F8 -179.6(4) . . . . ?
C25 O11 C28 F9 -58.9(7) . . . . ?
C25 O11 C28 F7 62.2(6) . . . . ?
C30 N8 C29 N7 178.2(4) . . . . ?
C30 N8 C29 S4 -1.9(4) . . . . ?
C35 S4 C29 N7 -178.6(4) . . . . ?
C35 S4 C29 N8 1.5(3) . . . . ?
C29 N8 C30 C35 1.3(5) . . . . ?
C29 N8 C30 C31 179.8(4) . . . . ?
N8 C30 C31 C32 -177.7(4) . . . . ?
C35 C30 C31 C32 0.6(6) . . . . ?
C30 C31 C32 C33 -0.3(7) . . . . ?
C31 C32 C33 C34 0.3(7) . . . . ?
C31 C32 C33 O12 173.6(4) . . . . ?
C36 O12 C33 C34 -104.9(6) . . . . ?
C36 O12 C33 C32 81.4(6) . . . . ?
C32 C33 C34 C35 -0.6(7) . . . . ?
O12 C33 C34 C35 -174.2(4) . . . . ?
C33 C34 C35 C30 0.9(6) . . . . ?
C33 C34 C35 S4 178.3(3) . . . . ?
N8 C30 C35 C34 177.6(4) . . . . ?
C31 C30 C35 C34 -1.0(6) . . . . ?
N8 C30 C35 S4 -0.2(5) . . . . ?
C31 C30 C35 S4 -178.7(3) . . . . ?
C29 S4 C35 C34 -178.4(4) . . . . ?
C29 S4 C35 C30 -0.7(3) . . . . ?
C33 O12 C36 F11 52.6(7) . . . . ?
C33 O12 C36 F12 172.8(4) . . . . ?
C33 O12 C36 F10 -69.1(6) . . . . ?
O3 C9 C10 O4 -178.9(4) . . . . ?
O2 C9 C10 O4 0.4(6) . . . . ?
O3 C9 C10 O5 1.4(6) . . . . ?
O2 C9 C10 O5 -179.3(4) . . . . ?
O6 C11 C12 O8 179.2(4) . . . . ?
O7 C11 C12 O8 0.7(6) . . . . ?
O6 C11 C12 O9 -1.4(6) . . . . ?
O7 C11 C12 O9 -180.0(4) . . . . ?

_refine_diff_density_max         0.433
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.062

####################################################################### 
# 
# 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_RZ-OA-190K-p21-c
_database_code_depnum_ccdc_archive 'CCDC 1828009'
_audit_update_record             
;
2018-03-07 deposited with the CCDC.
2018-03-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H6 F3 N2 O3 S'
_chemical_formula_weight         279.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.5229(13)
_cell_length_b                   10.1012(11)
_cell_length_c                   11.7207(14)
_cell_angle_alpha                90
_cell_angle_beta                 101.215(8)
_cell_angle_gamma                90
_cell_volume                     1105.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    3343
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      27.84

_exptl_crystal_description       Plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.677
_exptl_crystal_F_000             564
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.337
_shelx_estimated_absorpt_T_min   0.863
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.2390
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16095
_diffrn_reflns_av_unetI/netI     0.0731
_diffrn_reflns_av_R_equivalents  0.0949
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.684
_diffrn_reflns_theta_max         28.807
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2868
_reflns_number_gt                1841
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0898P)²+0.6776P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2868
_refine_ls_number_parameters     215
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.1073
_refine_ls_R_factor_gt           0.0738
_refine_ls_wR_factor_ref         0.2203
_refine_ls_wR_factor_gt          0.1959
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.099
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
F1A F 0.5901(6) 0.2906(13) 0.3306(6) 0.225(6) Uani 0.737(6) 1 d D . P A 1
F2A F 0.5817(5) 0.0489(5) 0.3865(6) 0.1155(19) Uani 0.737(6) 1 d D . P A 1
F3A F 0.6031(8) 0.1792(10) 0.5295(8) 0.173(4) Uani 0.737(6) 1 d D . P A 1
O1A O 0.4006(5) 0.1941(6) 0.3788(5) 0.099(2) Uani 0.737(6) 1 d D . P A 1
C8A C 0.5407(10) 0.1880(11) 0.4033(10) 0.179(8) Uani 0.737(6) 1 d D . P A 1
F1B F 0.6023(16) 0.2422(13) 0.4792(13) 0.072(4) Uani 0.263(6) 1 d D . P A 2
F2B F 0.5801(12) 0.1300(14) 0.3210(12) 0.089(4) Uani 0.263(6) 1 d D . P A 2
F3B F 0.4118(11) 0.0451(8) 0.4707(9) 0.082(4) Uani 0.263(6) 1 d D . P A 2
O1B O 0.4741(19) 0.2356(11) 0.3947(12) 0.081(5) Uani 0.263(6) 1 d D . P A 2
C8B C 0.526(2) 0.1229(16) 0.432(2) 0.179(8) Uani 0.263(6) 1 d D . P A 2
S1 S 0.16679(12) 0.42037(8) 0.69339(7) 0.0608(4) Uani 1 1 d . . . . .
O2 O 0.0414(3) 0.84113(18) 0.45831(17) 0.0588(7) Uani 1 1 d . . . . .
O3 O 0.0181(3) 0.91680(19) 0.63197(17) 0.0631(8) Uani 1 1 d . . . . .
N1 N 0.0490(4) 0.6572(3) 0.7198(2) 0.0560(8) Uani 1 1 d . . . . .
H1B H 0.027(5) 0.745(5) 0.698(4) 0.075(12) Uiso 1 1 d . . . . .
H1A H 0.038(4) 0.628(4) 0.791(4) 0.073(12) Uiso 1 1 d . . . . .
N2 N 0.1337(4) 0.6141(3) 0.5502(2) 0.0556(8) Uani 1 1 d . . . . .
H2 H 0.106(5) 0.697(5) 0.519(4) 0.075(12) Uiso 1 1 d . . . . .
C1 C 0.1092(4) 0.5797(3) 0.6545(2) 0.0500(8) Uani 1 1 d . . . . .
C2 C 0.2080(4) 0.5197(3) 0.4993(3) 0.0570(9) Uani 1 1 d . . . . .
C3 C 0.2519(5) 0.5285(4) 0.3937(3) 0.0745(12) Uani 1 1 d . . . . .
H3 H 0.234139 0.605844 0.347031 0.089 Uiso 1 1 calc R U . . .
C4 C 0.3226(6) 0.4209(5) 0.3582(4) 0.0849(14) Uani 1 1 d . . . . .
H4 H 0.353550 0.424143 0.285939 0.102 Uiso 1 1 calc R U . . .
C5 C 0.3481(5) 0.3106(5) 0.4256(4) 0.0806(13) Uani 1 1 d D . . . .
C6 C 0.3047(5) 0.2987(4) 0.5297(4) 0.0731(11) Uani 1 1 d . . . . .
H6 H 0.322157 0.220413 0.575099 0.088 Uiso 1 1 calc R U . . .
C7 C 0.2343(5) 0.4058(3) 0.5659(3) 0.0592(10) Uani 1 1 d . . . . .
C9 C 0.0167(4) 0.9303(3) 0.5267(2) 0.0456(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1A C8A 1.475(13) . ?
F2A C8A 1.482(10) . ?
F3A C8A 1.485(11) . ?
O1A C8A 1.311(10) . ?
O1A C5 1.430(6) . ?
F1B O1B 1.42(2) . ?
F1B C8B 1.458(14) . ?
F2B C8B 1.496(18) . ?
F3B C8B 1.479(14) . ?
O1B C8B 1.284(18) . ?
O1B C5 1.521(14) . ?
S1 C1 1.732(3) . ?
S1 C7 1.744(3) . ?
O2 C9 1.258(3) . ?
O3 C9 1.239(3) . ?
N1 C1 1.303(4) . ?
N1 H1B 0.94(5) . ?
N1 H1A 0.91(4) . ?
N2 C1 1.334(3) . ?
N2 C2 1.389(4) . ?
N2 H2 0.93(5) . ?
C2 C3 1.384(4) . ?
C2 C7 1.386(5) . ?
C3 C4 1.384(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.360(7) . ?
C4 H4 0.9500 . ?
C5 C6 1.368(6) . ?
C6 C7 1.382(5) . ?
C6 H6 0.9500 . ?
C9 C9 1.549(5) 3_576 ?

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
C8A O1A C5 111.8(5) . . ?
O1A C8A F1A 105.4(8) . . ?
O1A C8A F2A 107.3(8) . . ?
F1A C8A F2A 117.9(9) . . ?
O1A C8A F3A 114.5(9) . . ?
F1A C8A F3A 120.5(9) . . ?
F2A C8A F3A 90.6(8) . . ?
O1B F1B C8B 53.1(9) . . ?
C8B O1B F1B 65.2(11) . . ?
C8B O1B C5 128.9(14) . . ?
F1B O1B C5 115.0(11) . . ?
O1B C8B F1B 61.8(12) . . ?
O1B C8B F3B 108.6(16) . . ?
F1B C8B F3B 131.8(16) . . ?
O1B C8B F2B 80.3(13) . . ?
F1B C8B F2B 93.3(11) . . ?
F3B C8B F2B 133.5(16) . . ?
C1 S1 C7 90.20(15) . . ?
C1 N1 H1B 120(3) . . ?
C1 N1 H1A 119(3) . . ?
H1B N1 H1A 120(4) . . ?
C1 N2 C2 114.2(3) . . ?
C1 N2 H2 120(3) . . ?
C2 N2 H2 125(3) . . ?
N1 C1 N2 123.9(3) . . ?
N1 C1 S1 123.8(2) . . ?
N2 C1 S1 112.3(2) . . ?
C3 C2 C7 120.3(3) . . ?
C3 C2 N2 127.5(3) . . ?
C7 C2 N2 112.2(3) . . ?
C4 C3 C2 117.9(4) . . ?
C4 C3 H3 121.1 . . ?
C2 C3 H3 121.1 . . ?
C5 C4 C3 120.7(4) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 122.6(4) . . ?
C4 C5 O1A 119.2(5) . . ?
C6 C5 O1A 117.3(5) . . ?
C4 C5 O1B 109.3(6) . . ?
C6 C5 O1B 123.9(7) . . ?
C5 C6 C7 117.0(4) . . ?
C5 C6 H6 121.5 . . ?
C7 C6 H6 121.5 . . ?
C6 C7 C2 121.5(3) . . ?
C6 C7 S1 127.6(3) . . ?
C2 C7 S1 110.9(2) . . ?
O3 C9 O2 126.1(3) . . ?
O3 C9 C9 117.6(3) . 3_576 ?
O2 C9 C9 116.3(3) . 3_576 ?

_refine_diff_density_max         0.499
_refine_diff_density_min         -0.560
_refine_diff_density_rms         0.076

####################################################################### 
# 
# 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_RZ-OA-190K
_database_code_depnum_ccdc_archive 'CCDC 1572077'
_audit_update_record             
;
2017-11-25 deposited with the CCDC.
2018-03-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H12 F6 N4 O6 S2'
_chemical_formula_weight         558.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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'

_cell_length_a                   19.044(3)
_cell_length_b                   20.209(2)
_cell_length_c                   11.7215(14)
_cell_angle_alpha                90
_cell_angle_beta                 101.207(8)
_cell_angle_gamma                90
_cell_volume                     4425.1(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    190(2)
_cell_measurement_reflns_used    4250
_cell_measurement_theta_min      2.68
_cell_measurement_theta_max      29.61

_exptl_crystal_description       Plate
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.676
_exptl_crystal_F_000             2256
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.336
_shelx_estimated_absorpt_T_min   0.863
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.2390
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      190(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25786
_diffrn_reflns_av_unetI/netI     0.1819
_diffrn_reflns_av_R_equivalents  0.1056
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.484
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             7649
_reflns_number_gt                5165
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.997
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.996

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+7.8601P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.3(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         7649
_refine_ls_number_parameters     786
_refine_ls_number_restraints     339
_refine_ls_R_factor_all          0.1165
_refine_ls_R_factor_gt           0.0802
_refine_ls_wR_factor_ref         0.2591
_refine_ls_wR_factor_gt          0.2145
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.098
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 -0.2403(2) 0.66326(17) 0.2471(3) 0.0527(11) Uani 1 1 d . . . . .
S2 S 0.1085(2) 0.58087(15) -0.1331(3) 0.0411(9) Uani 1 1 d . . . . .
S3 S 0.2705(2) 0.66529(17) 0.2541(3) 0.0519(11) Uani 1 1 d . . . . .
S4 S 0.5879(2) 0.58853(15) -0.1398(3) 0.0459(10) Uani 1 1 d . . . . .
O2 O 0.1633(7) 0.2965(4) 0.0986(9) 0.054(3) Uani 1 1 d . . . . .
O3 O 0.1765(7) 0.3345(4) -0.0718(8) 0.056(3) Uani 1 1 d . . . . .
O4 O 0.2011(5) 0.4156(4) 0.1938(8) 0.039(2) Uani 1 1 d . . . . .
O5 O 0.2121(5) 0.4535(4) 0.0184(7) 0.035(2) Uani 1 1 d . . . . .
O9 O 0.6602(7) 0.2934(4) 0.0991(9) 0.061(3) Uani 1 1 d . . . . .
O10 O 0.6710(8) 0.3320(4) -0.0730(8) 0.067(4) Uani 1 1 d . . . . .
O11 O 0.6916(6) 0.4539(4) 0.0111(8) 0.049(3) Uani 1 1 d . . . . .
O12 O 0.6807(7) 0.4170(4) 0.1880(9) 0.051(3) Uani 1 1 d . . . . .
N1 N -0.3043(7) 0.5473(6) 0.2741(10) 0.043(3) Uani 1 1 d . . . . .
N2 N -0.2619(6) 0.5673(5) 0.1022(8) 0.035(2) Uani 1 1 d D . . . .
N3 N 0.1630(7) 0.7009(6) -0.1601(9) 0.048(3) Uani 1 1 d D . . . .
N4 N 0.1221(7) 0.6784(6) 0.0093(11) 0.047(3) Uani 1 1 d . . . . .
N5 N 0.2153(5) 0.5450(5) 0.2806(9) 0.038(3) Uani 1 1 d D . . . .
N6 N 0.2603(6) 0.5673(5) 0.1118(9) 0.037(3) Uani 1 1 d . . . . .
N7 N 0.6511(7) 0.7050(6) -0.1654(10) 0.046(3) Uani 1 1 d . . . . .
N8 N 0.6091(7) 0.6855(6) 0.0038(10) 0.046(3) Uani 1 1 d . . . . .
H6 H 0.248(7) 0.532(7) 0.093(11) 0.055 Uiso 1 1 d . U . . .
H8 H 0.625(7) 0.732(6) 0.042(10) 0.055 Uiso 1 1 d . U . . .
H2 H -0.285(4) 0.531(2) 0.064(7) 0.055 Uiso 1 1 d D U . . .
H4 H 0.133(7) 0.724(6) 0.048(10) 0.055 Uiso 1 1 d . U . . .
H1A H -0.316(7) 0.512(7) 0.256(12) 0.055 Uiso 1 1 d . U . . .
H1B H -0.305(7) 0.563(6) 0.352(11) 0.055 Uiso 1 1 d . U . . .
H3A H 0.158(6) 0.750(6) -0.145(11) 0.055 Uiso 1 1 d . U . . .
H3B H 0.166(6) 0.690(5) -0.235(3) 0.055 Uiso 1 1 d D U . . .
H5A H 0.181(3) 0.517(3) 0.248(8) 0.055 Uiso 1 1 d D U . . .
H5B H 0.192(7) 0.568(6) 0.344(10) 0.055 Uiso 1 1 d . U . . .
H7A H 0.656(7) 0.746(7) -0.142(11) 0.055 Uiso 1 1 d . U . . .
H7B H 0.622(7) 0.703(6) -0.243(10) 0.055 Uiso 1 1 d . U . . .
C1 C -0.2741(8) 0.5840(6) 0.2079(12) 0.036(3) Uani 1 1 d . . . . .
C2 C -0.2241(8) 0.6124(7) 0.0481(11) 0.044(3) Uani 1 1 d . . . . .
C3 C -0.2064(9) 0.6053(9) -0.0564(14) 0.061(4) Uani 1 1 d . . . . .
H3 H -0.220210 0.567500 -0.103606 0.073 Uiso 1 1 calc R U . . .
C4A C -0.1676(11) 0.6552(10) -0.0907(17) 0.077(5) Uani 1 1 d . . . . .
H4A1 H -0.148010 0.650487 -0.158867 0.092 Uiso 1 1 calc R U . A 1
C7 C -0.2085(8) 0.6691(7) 0.1169(13) 0.042(3) Uani 1 1 d . . . . .
C9 C 0.1786(8) 0.3403(6) 0.0324(12) 0.035(3) Uani 1 1 d . . . . .
C10 C 0.1995(8) 0.4090(6) 0.0877(12) 0.032(3) Uani 1 1 d . . . . .
C11 C 0.1341(8) 0.6605(6) -0.0940(11) 0.037(3) Uani 1 1 d . . . . .
C12 C 0.0868(8) 0.6290(7) 0.0580(12) 0.043(3) Uani 1 1 d . . . . .
C13 C 0.0618(10) 0.6325(8) 0.1636(12) 0.059(4) Uani 1 1 d . . . . .
H13 H 0.068026 0.671592 0.209502 0.070 Uiso 1 1 calc R U . . .
C14 C 0.0278(10) 0.5775(9) 0.1988(16) 0.072(6) Uani 1 1 d . . . . .
H14 H 0.012533 0.577628 0.271357 0.086 Uiso 1 1 calc R U . . .
C15 C 0.0166(7) 0.5236(8) 0.1285(15) 0.057(4) Uani 1 1 d D . . . .
C16 C 0.0377(7) 0.5187(7) 0.0278(14) 0.050(4) Uani 1 1 d . . . . .
H16 H 0.028450 0.479923 -0.018492 0.060 Uiso 1 1 calc R U . . .
C17 C 0.0739(8) 0.5723(7) -0.0082(13) 0.041(3) Uani 1 1 d . . . . .
C19 C 0.2458(8) 0.5841(6) 0.2148(12) 0.039(3) Uani 1 1 d . . . . .
C20 C 0.2956(7) 0.6161(6) 0.0588(10) 0.034(3) Uani 1 1 d . . . . .
C21 C 0.3161(8) 0.6132(7) -0.0454(13) 0.049(4) Uani 1 1 d . . . . .
H21 H 0.307668 0.574643 -0.092438 0.059 Uiso 1 1 calc R U . . .
C22 C 0.3496(9) 0.6679(8) -0.0816(14) 0.058(4) Uani 1 1 d . . . . .
H22 H 0.366056 0.666452 -0.153033 0.070 Uiso 1 1 calc R U . . .
C23 C 0.3595(9) 0.7254(7) -0.0136(14) 0.059(4) Uani 1 1 d . . . . .
C24 C 0.3344(9) 0.7309(7) 0.0904(13) 0.055(4) Uani 1 1 d . . . . .
H24 H 0.338197 0.770938 0.133632 0.066 Uiso 1 1 calc R U . . .
C25 C 0.3038(9) 0.6744(7) 0.1266(12) 0.045(4) Uani 1 1 d . . . . .
C27 C 0.6199(8) 0.6669(5) -0.0998(11) 0.035(3) Uani 1 1 d . . . . .
C28 C 0.5716(8) 0.6394(7) 0.0531(12) 0.045(4) Uani 1 1 d . . . . .
C29 C 0.5475(10) 0.6444(7) 0.1608(12) 0.055(4) Uani 1 1 d . . . . .
H29 H 0.556931 0.683053 0.207539 0.066 Uiso 1 1 calc R U . . .
C30 C 0.5095(10) 0.5908(7) 0.1964(15) 0.066(5) Uani 1 1 d . . . . .
H30 H 0.492007 0.592974 0.266849 0.079 Uiso 1 1 calc R U . . .
C31 C 0.4988(9) 0.5383(7) 0.1313(16) 0.065(5) Uani 1 1 d D . . . .
C32 C 0.5163(8) 0.5302(7) 0.0215(15) 0.055(4) Uani 1 1 d . . . . .
H32 H 0.504333 0.491695 -0.024525 0.066 Uiso 1 1 calc R U . . .
C33 C 0.5527(8) 0.5834(6) -0.0141(12) 0.045(4) Uani 1 1 d . . . . .
C35 C 0.6813(9) 0.4089(6) 0.0819(13) 0.043(4) Uani 1 1 d . . . . .
C36 C 0.6691(8) 0.3385(6) 0.0303(13) 0.039(3) Uani 1 1 d . . . . .
O8A O 0.4416(10) 0.4905(9) 0.158(2) 0.061(4) Uani 0.578(12) 1 d D . P B 1
C34A C 0.4199(12) 0.4361(14) 0.110(2) 0.075(4) Uani 0.578(12) 1 d D U P B 1
F10A F 0.3817(9) 0.4471(11) 0.0009(17) 0.095(6) Uani 0.578(12) 1 d D U P B 1
F12A F 0.4761(10) 0.3968(7) 0.0889(17) 0.094(5) Uani 0.578(12) 1 d D U P B 1
F11A F 0.3867(14) 0.3963(10) 0.162(2) 0.085(6) Uani 0.578(12) 1 d . U P B 1
O8B O 0.4743(15) 0.4810(13) 0.193(3) 0.061(4) Uani 0.422(12) 1 d D U P B 2
C34B C 0.4077(18) 0.4791(18) 0.187(3) 0.075(4) Uani 0.422(12) 1 d D U P B 2
F10B F 0.3779(14) 0.4866(15) 0.073(3) 0.086(6) Uani 0.422(12) 1 d D U P B 2
F11B F 0.394(2) 0.4215(19) 0.209(4) 0.122(10) Uani 0.422(12) 1 d . U P B 2
F12B F 0.3849(15) 0.5325(16) 0.239(2) 0.118(9) Uani 0.422(12) 1 d D U P B 2
F1A F -0.0282(7) 0.7010(7) -0.1205(13) 0.082(3) Uani 0.703(8) 1 d D . P C 1
F2A F -0.0155(8) 0.7493(6) 0.0425(14) 0.074(3) Uani 0.703(8) 1 d D . P C 1
F3A F -0.0238(8) 0.8064(7) -0.1168(15) 0.091(4) Uani 0.703(8) 1 d D . P C 1
O1A O -0.1160(8) 0.7577(7) -0.0778(16) 0.059(4) Uani 0.703(8) 1 d D . P C 1
C5A C -0.1570(11) 0.7114(12) -0.028(2) 0.058(6) Uani 0.703(8) 1 d D . P C 1
C6A C -0.1765(10) 0.7209(14) 0.075(2) 0.046(5) Uani 0.703(8) 1 d D . P C 1
H6A1 H -0.168316 0.761637 0.115951 0.055 Uiso 0.703(8) 1 calc R U P C 1
C8A C -0.0467(13) 0.7535(7) -0.0661(17) 0.085(8) Uani 0.703(8) 1 d D . P C 1
F1B F -0.0219(16) 0.7900(18) 0.113(3) 0.082(3) Uani 0.297(8) 1 d D . P C 2
F2B F -0.1097(15) 0.8491(14) 0.038(3) 0.074(3) Uani 0.297(8) 1 d D . P C 2
F3B F -0.019(2) 0.847(2) -0.038(4) 0.091(4) Uani 0.297(8) 1 d D . P C 2
O1B O -0.1199(19) 0.7850(16) -0.047(4) 0.059(4) Uani 0.297(8) 1 d D . P C 2
C5B C -0.126(2) 0.719(2) -0.006(5) 0.058(6) Uani 0.297(8) 1 d D . P C 2
C6B C -0.149(2) 0.722(4) 0.096(5) 0.046(5) Uani 0.297(8) 1 d D . P C 2
H6B H -0.130845 0.754356 0.152759 0.055 Uiso 0.297(8) 1 calc R U P C 2
C8B C -0.0596(17) 0.8089(18) 0.012(3) 0.085(8) Uani 0.297(8) 1 d D . P C 2
O7A O 0.3792(8) 0.7883(7) -0.0556(14) 0.047(4) Uani 0.704(15) 1 d . . P D 1
F7A F 0.4689(11) 0.8550(8) -0.0633(18) 0.087(5) Uani 0.704(15) 1 d . . P D 1
F8A F 0.4871(8) 0.7842(8) 0.0611(18) 0.081(5) Uani 0.704(15) 1 d . U P D 1
F9A F 0.4782(8) 0.7518(7) -0.1163(15) 0.097(5) Uani 0.704(15) 1 d . U P D 1
C26A C 0.4487(12) 0.7926(12) -0.043(3) 0.066(5) Uani 0.704(15) 1 d . U P D 1
O7B O 0.404(3) 0.765(2) -0.063(4) 0.067(10) Uani 0.296(15) 1 d . U P D 2
F7B F 0.466(3) 0.8374(18) -0.118(4) 0.087(5) Uani 0.296(15) 1 d . U P D 2
F8B F 0.473(2) 0.804(3) 0.110(4) 0.086(10) Uani 0.296(15) 1 d . U P D 2
F9B F 0.3879(18) 0.8524(12) 0.033(2) 0.070(8) Uani 0.296(15) 1 d . U P D 2
C26B C 0.438(3) 0.817(2) 0.018(5) 0.060(8) Uani 0.296(15) 1 d . U P D 2
F4A F -0.1066(9) 0.3999(11) 0.165(2) 0.105(4) Uani 0.722(18) 1 d D . P E 1
F5A F -0.1183(10) 0.4809(11) 0.0409(18) 0.105(4) Uani 0.722(18) 1 d D . P E 1
F6A F -0.1162(8) 0.5040(9) 0.2088(16) 0.105(4) Uani 0.722(18) 1 d D . P E 1
O6A O -0.0169(10) 0.4688(10) 0.177(2) 0.076(8) Uani 0.722(18) 1 d D . P E 1
C18A C -0.0893(11) 0.4610(8) 0.1436(19) 0.062(6) Uani 0.722(18) 1 d D . P E 1
F4B F -0.110(2) 0.439(3) 0.222(5) 0.105(4) Uani 0.278(18) 1 d D . P E 2
F5B F -0.130(2) 0.485(3) 0.080(5) 0.105(4) Uani 0.278(18) 1 d D . P E 2
F6B F -0.107(2) 0.542(2) 0.223(4) 0.105(4) Uani 0.278(18) 1 d D . P E 2
O6B O -0.023(3) 0.4643(19) 0.139(7) 0.076(8) Uani 0.278(18) 1 d D . P E 2
C18B C -0.082(3) 0.4902(19) 0.175(5) 0.062(6) Uani 0.278(18) 1 d D . P E 2


_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 C7 1.752(14) . ?
S1 C1 1.754(13) . ?
S2 C11 1.718(12) . ?
S2 C17 1.727(15) . ?
S3 C25 1.743(13) . ?
S3 C19 1.745(13) . ?
S4 C27 1.727(12) . ?
S4 C33 1.737(14) . ?
O2 C9 1.248(16) . ?
O3 C9 1.221(17) . ?
O4 C10 1.244(16) . ?
O5 C10 1.266(15) . ?
O9 C36 1.250(16) . ?
O10 C36 1.225(17) . ?
O11 C35 1.273(16) . ?
O12 C35 1.256(17) . ?
N1 C1 1.286(17) . ?
N1 H1A 0.77(14) . ?
N1 H1B 0.97(12) . ?
N2 C1 1.347(16) . ?
N2 C2 1.389(18) . ?
N2 H2 0.9200(16) . ?
N3 C11 1.316(16) . ?
N3 H3A 1.02(13) . ?
N3 H3B 0.9200(16) . ?
N4 C11 1.325(17) . ?
N4 C12 1.386(18) . ?
N4 H4 1.04(13) . ?
N5 C19 1.315(16) . ?
N5 H5A 0.8900(16) . ?
N5 H5B 1.04(12) . ?
N6 C19 1.334(17) . ?
N6 C20 1.404(15) . ?
N6 H6 0.76(13) . ?
N7 C27 1.309(16) . ?
N7 H7A 0.88(14) . ?
N7 H7B 0.97(12) . ?
N8 C27 1.326(17) . ?
N8 C28 1.368(19) . ?
N8 H8 1.06(12) . ?
C2 C3 1.339(19) . ?
C2 C7 1.40(2) . ?
C3 C4A 1.36(3) . ?
C3 H3 0.9500 . ?
C4A C5A 1.35(3) . ?
C4A C5B 1.73(6) . ?
C4A H4A1 0.9500 . ?
C7 C6A 1.35(3) . ?
C7 C6B 1.61(6) . ?
C9 C10 1.551(12) . ?
C12 C17 1.38(2) . ?
C12 C13 1.412(19) . ?
C13 C14 1.39(2) . ?
C13 H13 0.9500 . ?
C14 C15 1.36(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.32(2) . ?
C15 O6B 1.44(3) . ?
C15 O6A 1.45(2) . ?
C16 C17 1.39(2) . ?
C16 H16 0.9500 . ?
C20 C21 1.353(19) . ?
C20 C25 1.414(18) . ?
C21 C22 1.38(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.40(2) . ?
C22 H22 0.9500 . ?
C23 O7B 1.36(4) . ?
C23 C24 1.40(2) . ?
C23 O7A 1.438(19) . ?
C24 C25 1.385(18) . ?
C24 H24 0.9500 . ?
C28 C33 1.39(2) . ?
C28 C29 1.428(19) . ?
C29 C30 1.41(2) . ?
C29 H29 0.9500 . ?
C30 C31 1.30(2) . ?
C30 H30 0.9500 . ?
C31 C32 1.40(2) . ?
C31 O8B 1.49(2) . ?
C31 O8A 1.53(2) . ?
C32 C33 1.385(19) . ?
C32 H32 0.9500 . ?
C35 C36 1.545(12) . ?
O8A C34A 1.27(3) . ?
C34A F11A 1.25(3) . ?
C34A F10A 1.36(2) . ?
C34A F12A 1.39(2) . ?
O8B C34B 1.26(4) . ?
C34B F11B 1.23(5) . ?
C34B F12B 1.36(3) . ?
C34B F10B 1.36(3) . ?
F1A C8A 1.321(19) . ?
F2A C8A 1.298(18) . ?
F3A C8A 1.336(18) . ?
O1A C8A 1.30(3) . ?
O1A C5A 1.42(2) . ?
C5A C6A 1.34(3) . ?
C6A H6A1 0.9500 . ?
F1B C8B 1.31(2) . ?
F2B C8B 1.33(2) . ?
F2B O1B 1.63(5) . ?
F3B C8B 1.31(2) . ?
O1B C8B 1.31(3) . ?
O1B C5B 1.43(3) . ?
C5B C6B 1.34(3) . ?
C6B H6B 0.9500 . ?
O7A C26A 1.31(3) . ?
F7A C26A 1.35(3) . ?
F8A C26A 1.31(3) . ?
F9A C26A 1.39(3) . ?
O7B C26B 1.49(7) . ?
F7B C26B 1.82(7) . ?
F8B C26B 1.19(6) . ?
F9B C26B 1.24(7) . ?
F4A C18A 1.315(18) . ?
F5A C18A 1.288(19) . ?
F6A C18A 1.324(17) . ?
O6A C18A 1.37(2) . ?
F4B C18B 1.33(2) . ?
F5B C18B 1.31(3) . ?
F6B C18B 1.32(2) . ?
O6B C18B 1.37(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 S1 C1 90.2(7) . . ?
C11 S2 C17 90.2(6) . . ?
C25 S3 C19 89.9(6) . . ?
C27 S4 C33 89.9(6) . . ?
C1 N1 H1A 121(10) . . ?
C1 N1 H1B 117(8) . . ?
H1A N1 H1B 121(10) . . ?
C1 N2 C2 117.0(10) . . ?
C1 N2 H2 120(6) . . ?
C2 N2 H2 123(6) . . ?
C11 N3 H3A 116(7) . . ?
C11 N3 H3B 122(7) . . ?
H3A N3 H3B 115(9) . . ?
C11 N4 C12 111.4(12) . . ?
C11 N4 H4 126(7) . . ?
C12 N4 H4 122(7) . . ?
C19 N5 H5A 120(7) . . ?
C19 N5 H5B 116(7) . . ?
H5A N5 H5B 103(9) . . ?
C19 N6 C20 115.0(10) . . ?
C19 N6 H6 113(10) . . ?
C20 N6 H6 132(10) . . ?
C27 N7 H7A 114(8) . . ?
C27 N7 H7B 107(7) . . ?
H7A N7 H7B 110(10) . . ?
C27 N8 C28 112.3(12) . . ?
C27 N8 H8 124(7) . . ?
C28 N8 H8 124(7) . . ?
N1 C1 N2 126.1(11) . . ?
N1 C1 S1 123.4(11) . . ?
N2 C1 S1 110.4(9) . . ?
C3 C2 N2 126.3(14) . . ?
C3 C2 C7 123.6(14) . . ?
N2 C2 C7 110.1(11) . . ?
C2 C3 C4A 116.1(17) . . ?
C2 C3 H3 122.0 . . ?
C4A C3 H3 122.0 . . ?
C5A C4A C3 119.8(16) . . ?
C3 C4A C5B 127(2) . . ?
C5A C4A H4A1 120.1 . . ?
C3 C4A H4A1 120.1 . . ?
C6A C7 C2 119.0(16) . . ?
C2 C7 C6B 122(3) . . ?
C6A C7 S1 128.7(15) . . ?
C2 C7 S1 112.2(10) . . ?
C6B C7 S1 123(2) . . ?
O3 C9 O2 126.0(12) . . ?
O3 C9 C10 117.4(9) . . ?
O2 C9 C10 116.6(9) . . ?
O4 C10 O5 126.4(12) . . ?
O4 C10 C9 117.9(8) . . ?
O5 C10 C9 115.7(9) . . ?
N3 C11 N4 122.3(11) . . ?
N3 C11 S2 123.6(10) . . ?
N4 C11 S2 114.1(10) . . ?
C17 C12 N4 114.4(12) . . ?
C17 C12 C13 118.7(13) . . ?
N4 C12 C13 126.8(14) . . ?
C14 C13 C12 118.5(16) . . ?
C14 C13 H13 120.7 . . ?
C12 C13 H13 120.7 . . ?
C15 C14 C13 119.3(16) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C16 C15 C14 124.2(15) . . ?
C16 C15 O6B 106(3) . . ?
C14 C15 O6B 130(3) . . ?
C16 C15 O6A 121.9(19) . . ?
C14 C15 O6A 113.8(18) . . ?
C15 C16 C17 117.8(15) . . ?
C15 C16 H16 121.1 . . ?
C17 C16 H16 121.1 . . ?
C12 C17 C16 121.4(14) . . ?
C12 C17 S2 109.8(10) . . ?
C16 C17 S2 128.8(12) . . ?
N5 C19 N6 124.9(11) . . ?
N5 C19 S3 122.5(10) . . ?
N6 C19 S3 112.7(9) . . ?
C21 C20 N6 128.0(11) . . ?
C21 C20 C25 121.6(11) . . ?
N6 C20 C25 110.3(10) . . ?
C20 C21 C22 118.2(12) . . ?
C20 C21 H21 120.9 . . ?
C22 C21 H21 120.9 . . ?
C21 C22 C23 120.5(14) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
O7B C23 C24 132(2) . . ?
O7B C23 C22 106(2) . . ?
C24 C23 C22 122.1(12) . . ?
C24 C23 O7A 112.6(14) . . ?
C22 C23 O7A 123.6(14) . . ?
C25 C24 C23 115.9(13) . . ?
C25 C24 H24 122.0 . . ?
C23 C24 H24 122.0 . . ?
C24 C25 C20 121.5(12) . . ?
C24 C25 S3 126.5(11) . . ?
C20 C25 S3 112.0(9) . . ?
N7 C27 N8 122.6(11) . . ?
N7 C27 S4 123.8(10) . . ?
N8 C27 S4 113.6(10) . . ?
N8 C28 C33 114.6(12) . . ?
N8 C28 C29 127.5(13) . . ?
C33 C28 C29 117.9(13) . . ?
C30 C29 C28 118.5(14) . . ?
C30 C29 H29 120.7 . . ?
C28 C29 H29 120.7 . . ?
C31 C30 C29 119.0(14) . . ?
C31 C30 H30 120.5 . . ?
C29 C30 H30 120.5 . . ?
C30 C31 C32 126.6(13) . . ?
C30 C31 O8B 112.1(19) . . ?
C32 C31 O8B 120.8(18) . . ?
C30 C31 O8A 115.7(15) . . ?
C32 C31 O8A 114.7(17) . . ?
C33 C32 C31 114.2(14) . . ?
C33 C32 H32 122.9 . . ?
C31 C32 H32 122.9 . . ?
C32 C33 C28 123.5(13) . . ?
C32 C33 S4 126.9(11) . . ?
C28 C33 S4 109.4(10) . . ?
O12 C35 O11 125.7(12) . . ?
O12 C35 C36 118.6(9) . . ?
O11 C35 C36 115.7(9) . . ?
O10 C36 O9 126.4(11) . . ?
O10 C36 C35 117.0(9) . . ?
O9 C36 C35 116.6(9) . . ?
C34A O8A C31 130(2) . . ?
F11A C34A O8A 120(3) . . ?
F11A C34A F10A 110(2) . . ?
O8A C34A F10A 110(2) . . ?
F11A C34A F12A 101(2) . . ?
O8A C34A F12A 112(2) . . ?
F10A C34A F12A 103(2) . . ?
C34B O8B C31 114(3) . . ?
F11B C34B O8B 106(3) . . ?
F11B C34B F12B 124(4) . . ?
O8B C34B F12B 111(3) . . ?
F11B C34B F10B 104(3) . . ?
O8B C34B F10B 106(3) . . ?
F12B C34B F10B 104(3) . . ?
C8A O1A C5A 122.9(15) . . ?
C6A C5A C4A 125.0(19) . . ?
C6A C5A O1A 123(2) . . ?
C4A C5A O1A 112(2) . . ?
C5A C6A C7 116(2) . . ?
C5A C6A H6A1 122.0 . . ?
C7 C6A H6A1 122.0 . . ?
F2A C8A O1A 112(2) . . ?
F2A C8A F1A 107.9(16) . . ?
O1A C8A F1A 111.1(17) . . ?
F2A C8A F3A 111.2(17) . . ?
O1A C8A F3A 108.3(16) . . ?
F1A C8A F3A 106.7(18) . . ?
C8B F2B O1B 51.5(18) . . ?
C8B O1B C5B 107(4) . . ?
C8B O1B F2B 52.7(18) . . ?
C5B O1B F2B 122(4) . . ?
C6B C5B O1B 109(5) . . ?
C6B C5B C4A 111(4) . . ?
O1B C5B C4A 124(4) . . ?
C5B C6B C7 118(4) . . ?
C5B C6B H6B 121.1 . . ?
C7 C6B H6B 121.1 . . ?
F3B C8B O1B 121(4) . . ?
F3B C8B F1B 107(4) . . ?
O1B C8B F1B 130(3) . . ?
F3B C8B F2B 105(3) . . ?
O1B C8B F2B 76(3) . . ?
F1B C8B F2B 105(3) . . ?
C26A O7A C23 110.4(14) . . ?
O7A C26A F8A 118(2) . . ?
O7A C26A F7A 111.1(19) . . ?
F8A C26A F7A 99(2) . . ?
O7A C26A F9A 115(3) . . ?
F8A C26A F9A 106.2(18) . . ?
F7A C26A F9A 106.5(19) . . ?
C23 O7B C26B 113(4) . . ?
F8B C26B F9B 108(6) . . ?
F8B C26B O7B 122(5) . . ?
F9B C26B O7B 104(5) . . ?
F8B C26B F7B 130(5) . . ?
F9B C26B F7B 111(4) . . ?
O7B C26B F7B 77(4) . . ?
C18A O6A C15 118.0(16) . . ?
F5A C18A F4A 113.1(19) . . ?
F5A C18A F6A 101.0(18) . . ?
F4A C18A F6A 111.5(17) . . ?
F5A C18A O6A 117.3(16) . . ?
F4A C18A O6A 109.3(16) . . ?
F6A C18A O6A 104(2) . . ?
C18B O6B C15 100(3) . . ?
F5B C18B F6B 100(5) . . ?
F5B C18B F4B 91(4) . . ?
F6B C18B F4B 104(4) . . ?
F5B C18B O6B 101(5) . . ?
F6B C18B O6B 145(5) . . ?
F4B C18B O6B 104(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N2 C1 N1 -175.7(15) . . . . ?
C2 N2 C1 S1 2.5(15) . . . . ?
C7 S1 C1 N1 176.8(13) . . . . ?
C7 S1 C1 N2 -1.5(11) . . . . ?
C1 N2 C2 C3 179.9(15) . . . . ?
C1 N2 C2 C7 -2.3(17) . . . . ?
N2 C2 C3 C4A -178.3(16) . . . . ?
C7 C2 C3 C4A 4(3) . . . . ?
C2 C3 C4A C5A -8(3) . . . . ?
C2 C3 C4A C5B 12(3) . . . . ?
C3 C2 C7 C6A 3(2) . . . . ?
N2 C2 C7 C6A -175.2(15) . . . . ?
C3 C2 C7 C6B -18(3) . . . . ?
N2 C2 C7 C6B 164(3) . . . . ?
C3 C2 C7 S1 178.9(13) . . . . ?
N2 C2 C7 S1 1.0(16) . . . . ?
C1 S1 C7 C6A 176.0(17) . . . . ?
C1 S1 C7 C2 0.3(12) . . . . ?
C1 S1 C7 C6B -163(3) . . . . ?
O3 C9 C10 O4 179.4(16) . . . . ?
O2 C9 C10 O4 1.5(16) . . . . ?
O3 C9 C10 O5 0.5(16) . . . . ?
O2 C9 C10 O5 -177.4(16) . . . . ?
C12 N4 C11 N3 175.8(15) . . . . ?
C12 N4 C11 S2 -4.1(17) . . . . ?
C17 S2 C11 N3 -175.8(15) . . . . ?
C17 S2 C11 N4 4.1(13) . . . . ?
C11 N4 C12 C17 1.9(18) . . . . ?
C11 N4 C12 C13 -175.9(15) . . . . ?
C17 C12 C13 C14 3(2) . . . . ?
N4 C12 C13 C14 -179.6(15) . . . . ?
C12 C13 C14 C15 -3(3) . . . . ?
C13 C14 C15 C16 2(3) . . . . ?
C13 C14 C15 O6B -173(4) . . . . ?
C13 C14 C15 O6A 177.7(16) . . . . ?
C14 C15 C16 C17 0(2) . . . . ?
O6B C15 C16 C17 176(3) . . . . ?
O6A C15 C16 C17 -175.5(14) . . . . ?
N4 C12 C17 C16 -178.8(13) . . . . ?
C13 C12 C17 C16 -1(2) . . . . ?
N4 C12 C17 S2 1.2(16) . . . . ?
C13 C12 C17 S2 179.1(12) . . . . ?
C15 C16 C17 C12 -1(2) . . . . ?
C15 C16 C17 S2 179.4(12) . . . . ?
C11 S2 C17 C12 -2.8(12) . . . . ?
C11 S2 C17 C16 177.1(14) . . . . ?
C20 N6 C19 N5 -177.6(14) . . . . ?
C20 N6 C19 S3 3.3(16) . . . . ?
C25 S3 C19 N5 179.2(14) . . . . ?
C25 S3 C19 N6 -1.7(12) . . . . ?
C19 N6 C20 C21 -179.1(15) . . . . ?
C19 N6 C20 C25 -3.4(18) . . . . ?
N6 C20 C21 C22 179.1(16) . . . . ?
C25 C20 C21 C22 4(2) . . . . ?
C20 C21 C22 C23 -2(3) . . . . ?
C21 C22 C23 O7B 170(3) . . . . ?
C21 C22 C23 C24 -2(3) . . . . ?
C21 C22 C23 O7A -166.0(16) . . . . ?
O7B C23 C24 C25 -165(4) . . . . ?
C22 C23 C24 C25 4(3) . . . . ?
O7A C23 C24 C25 170.1(14) . . . . ?
C23 C24 C25 C20 -3(2) . . . . ?
C23 C24 C25 S3 177.9(13) . . . . ?
C21 C20 C25 C24 -1(2) . . . . ?
N6 C20 C25 C24 -177.2(15) . . . . ?
C21 C20 C25 S3 178.1(12) . . . . ?
N6 C20 C25 S3 2.0(16) . . . . ?
C19 S3 C25 C24 179.0(16) . . . . ?
C19 S3 C25 C20 -0.3(12) . . . . ?
C28 N8 C27 N7 176.1(14) . . . . ?
C28 N8 C27 S4 -3.1(16) . . . . ?
C33 S4 C27 N7 -175.1(14) . . . . ?
C33 S4 C27 N8 4.1(12) . . . . ?
C27 N8 C28 C33 -0.1(18) . . . . ?
C27 N8 C28 C29 -176.7(14) . . . . ?
N8 C28 C29 C30 -179.9(15) . . . . ?
C33 C28 C29 C30 4(2) . . . . ?
C28 C29 C30 C31 1(3) . . . . ?
C29 C30 C31 C32 -5(3) . . . . ?
C29 C30 C31 O8B 166.1(19) . . . . ?
C29 C30 C31 O8A -164.6(17) . . . . ?
C30 C31 C32 C33 4(3) . . . . ?
O8B C31 C32 C33 -166.6(19) . . . . ?
O8A C31 C32 C33 163.6(14) . . . . ?
C31 C32 C33 C28 1(2) . . . . ?
C31 C32 C33 S4 175.4(12) . . . . ?
N8 C28 C33 C32 178.2(14) . . . . ?
C29 C28 C33 C32 -5(2) . . . . ?
N8 C28 C33 S4 3.1(16) . . . . ?
C29 C28 C33 S4 -179.9(11) . . . . ?
C27 S4 C33 C32 -178.8(15) . . . . ?
C27 S4 C33 C28 -3.9(11) . . . . ?
O12 C35 C36 O10 -178.9(18) . . . . ?
O11 C35 C36 O10 0.6(18) . . . . ?
O12 C35 C36 O9 -0.8(18) . . . . ?
O11 C35 C36 O9 178.8(18) . . . . ?
C30 C31 O8A C34A -180(2) . . . . ?
C32 C31 O8A C34A 19(3) . . . . ?
C31 O8A C34A F11A 161(2) . . . . ?
C31 O8A C34A F10A -70(3) . . . . ?
C31 O8A C34A F12A 43(3) . . . . ?
C30 C31 O8B C34B 87(3) . . . . ?
C32 C31 O8B C34B -101(3) . . . . ?
C31 O8B C34B F11B 160(3) . . . . ?
C31 O8B C34B F12B -63(4) . . . . ?
C31 O8B C34B F10B 49(4) . . . . ?
C3 C4A C5A C6A 6(3) . . . . ?
C3 C4A C5A O1A -179.4(18) . . . . ?
C8A O1A C5A C6A 96(3) . . . . ?
C8A O1A C5A C4A -79(3) . . . . ?
C4A C5A C6A C7 1(3) . . . . ?
O1A C5A C6A C7 -172.9(17) . . . . ?
C2 C7 C6A C5A -5(3) . . . . ?
S1 C7 C6A C5A 179.5(14) . . . . ?
C5A O1A C8A F2A -54(3) . . . . ?
C5A O1A C8A F1A 67(3) . . . . ?
C5A O1A C8A F3A -176(2) . . . . ?
C8B F2B O1B C5B 87(4) . . . . ?
C8B O1B C5B C6B 79(4) . . . . ?
F2B O1B C5B C6B 23(5) . . . . ?
C8B O1B C5B C4A -148(3) . . . . ?
F2B O1B C5B C4A 156(3) . . . . ?
C3 C4A C5B C6B -13(5) . . . . ?
C3 C4A C5B O1B -145(3) . . . . ?
O1B C5B C6B C7 139(4) . . . . ?
C4A C5B C6B C7 -1(6) . . . . ?
C2 C7 C6B C5B 15(6) . . . . ?
S1 C7 C6B C5B 176(3) . . . . ?
C5B O1B C8B F3B 142(4) . . . . ?
F2B O1B C8B F3B -99(4) . . . . ?
C5B O1B C8B F1B -21(6) . . . . ?
F2B O1B C8B F1B 98(4) . . . . ?
C5B O1B C8B F2B -118(4) . . . . ?
O1B F2B C8B F3B 119(4) . . . . ?
O1B F2B C8B F1B -128(3) . . . . ?
C24 C23 O7A C26A 108(2) . . . . ?
C22 C23 O7A C26A -86(3) . . . . ?
C23 O7A C26A F8A -56(3) . . . . ?
C23 O7A C26A F7A -169(2) . . . . ?
C23 O7A C26A F9A 70(2) . . . . ?
C24 C23 O7B C26B 9(7) . . . . ?
C22 C23 O7B C26B -162(4) . . . . ?
C23 O7B C26B F8B 57(8) . . . . ?
C23 O7B C26B F9B -65(5) . . . . ?
C23 O7B C26B F7B -174(4) . . . . ?
C16 C15 O6A C18A -86(3) . . . . ?
C14 C15 O6A C18A 98(3) . . . . ?
C15 O6A C18A F5A 30(3) . . . . ?
C15 O6A C18A F4A 160(2) . . . . ?
C15 O6A C18A F6A -81(3) . . . . ?
C16 C15 O6B C18B -134(5) . . . . ?
C14 C15 O6B C18B 41(7) . . . . ?
C15 O6B C18B F5B 106(5) . . . . ?
C15 O6B C18B F6B -20(12) . . . . ?
C15 O6B C18B F4B -161(5) . . . . ?

_refine_diff_density_max         0.643
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.082

