# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_xb0557_0m
_database_code_depnum_ccdc_archive 'CCDC 1571172'
_audit_update_record             
;
2018-08-24 deposited with the CCDC.	2019-03-04 downloaded from the CCDC.
;
_audit_creation_date             2017-11-21
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C15 H15 N O5 S'
_chemical_formula_sum            'C15 H15 N O5 S'
_chemical_formula_weight         321.34
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.2237(15)
_cell_length_b                   10.551(3)
_cell_length_c                   12.693(3)
_cell_angle_alpha                98.868(4)
_cell_angle_beta                 99.615(4)
_cell_angle_gamma                106.235(4)
_cell_volume                     771.0(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1083
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.16
_cell_measurement_theta_min      3.33
_shelx_estimated_absorpt_T_max   0.965
_shelx_estimated_absorpt_T_min   0.922
_exptl_absorpt_coefficient_mu    0.232
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6368
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0687 before and 0.0324 after correction.
The Ratio of minimum to maximum transmission is 0.8543.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             336
_exptl_crystal_size_max          0.356
_exptl_crystal_size_mid          0.274
_exptl_crystal_size_min          0.153
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4227
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.415
_diffrn_reflns_theta_min         2.057
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2165
_reflns_number_total             3034
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         3034
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0526
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0697P)²+0.0561P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1304
_refine_ls_wR_factor_ref         0.1423
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C9(H9), C10(H10)
2.c Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.28550(12) 0.12694(7) 0.36966(5) 0.0537(2) Uani 1 1 d . . . . .
N1 N 0.2824(3) -0.1245(2) 0.37835(15) 0.0444(5) Uani 1 1 d . . . . .
O1 O 0.4545(3) -0.04044(17) 0.25454(13) 0.0492(4) Uani 1 1 d . . . . .
O2 O 0.2238(3) 0.16950(17) -0.02983(13) 0.0498(5) Uani 1 1 d . . . . .
O3 O 0.0922(3) 0.2635(3) -0.15699(19) 0.1017(10) Uani 1 1 d . . . . .
O4 O 0.7462(3) 0.5405(2) -0.12113(15) 0.0665(6) Uani 1 1 d . . . . .
O5 O 0.4000(3) 0.44708(18) -0.23129(14) 0.0571(5) Uani 1 1 d . . . . .
C1 C 0.1434(5) -0.1277(3) 0.4603(2) 0.0610(7) Uani 1 1 d . . . . .
H1A H 0.187881 -0.039778 0.507147 0.091 Uiso 1 1 calc GR . . . .
H1B H 0.166626 -0.192127 0.503179 0.091 Uiso 1 1 calc GR . . . .
H1C H -0.015657 -0.153271 0.424621 0.091 Uiso 1 1 calc GR . . . .
C2 C 0.3334(5) -0.2485(3) 0.3408(2) 0.0588(7) Uani 1 1 d . . . . .
H2A H 0.215098 -0.303729 0.279082 0.088 Uiso 1 1 calc GR . . . .
H2B H 0.340292 -0.296882 0.398714 0.088 Uiso 1 1 calc GR . . . .
H2C H 0.478381 -0.226324 0.319745 0.088 Uiso 1 1 calc GR . . . .
C3 C 0.3374(4) -0.0174(2) 0.33354(18) 0.0406(5) Uani 1 1 d . . . . .
C4 C 0.5054(4) 0.0540(2) 0.18899(18) 0.0426(6) Uani 1 1 d . . . . .
C5 C 0.3350(4) 0.0655(2) 0.11113(18) 0.0439(6) Uani 1 1 d . . . . .
H5 H 0.182894 0.013667 0.102581 0.053 Uiso 1 1 calc R . . . .
C6 C 0.3959(4) 0.1561(2) 0.04619(17) 0.0392(5) Uani 1 1 d . . . . .
C7 C 0.6236(4) 0.2337(2) 0.05601(18) 0.0404(5) Uani 1 1 d . . . . .
C8 C 0.7923(4) 0.2143(3) 0.1339(2) 0.0537(7) Uani 1 1 d . . . . .
H8 H 0.945729 0.262517 0.140850 0.064 Uiso 1 1 calc R . . . .
C9 C 0.7341(4) 0.1250(3) 0.2002(2) 0.0515(7) Uani 1 1 d . . . . .
H9 H 0.846794 0.112498 0.251914 0.062 Uiso 1 1 calc R . . . .
C10 C 0.6659(4) 0.3299(2) -0.01124(18) 0.0445(6) Uani 1 1 d . . . . .
H10 H 0.816172 0.383192 -0.005054 0.053 Uiso 1 1 calc R . . . .
C11 C 0.4972(4) 0.3472(2) -0.08347(18) 0.0420(6) Uani 1 1 d . . . . .
C12 C 0.2593(4) 0.2624(3) -0.0966(2) 0.0538(7) Uani 1 1 d . . . . .
C13 C 0.5605(4) 0.4552(3) -0.14592(19) 0.0463(6) Uani 1 1 d . . . . .
C14 C 0.4599(6) 0.5492(3) -0.2964(2) 0.0678(8) Uani 1 1 d . . . . .
H14A H 0.596163 0.545790 -0.322814 0.081 Uiso 1 1 calc R . . . .
H14B H 0.490104 0.638729 -0.252587 0.081 Uiso 1 1 calc R . . . .
C15 C 0.2635(8) 0.5190(4) -0.3887(3) 0.136(2) Uani 1 1 d . . . . .
H15A H 0.232818 0.429256 -0.430213 0.204 Uiso 1 1 calc GR . . . .
H15B H 0.298280 0.582699 -0.434711 0.204 Uiso 1 1 calc GR . . . .
H15C H 0.130997 0.525226 -0.361549 0.204 Uiso 1 1 calc GR . . . .


_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 C3 1.656(2) . ?
N1 C1 1.458(3) . ?
N1 C2 1.460(3) . ?
N1 C3 1.328(3) . ?
O1 C3 1.366(3) . ?
O1 C4 1.397(3) . ?
O2 C6 1.371(3) . ?
O2 C12 1.388(3) . ?
O3 C12 1.188(3) . ?
O4 C13 1.206(3) . ?
O5 C13 1.320(3) . ?
O5 C14 1.461(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C4 C5 1.370(3) . ?
C4 C9 1.382(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.371(3) . ?
C6 C7 1.398(3) . ?
C7 C8 1.399(3) . ?
C7 C10 1.422(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.372(3) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C10 C11 1.346(3) . ?
C11 C12 1.467(3) . ?
C11 C13 1.488(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.469(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 116.7(2) . . ?
C3 N1 C1 120.2(2) . . ?
C3 N1 C2 122.7(2) . . ?
C3 O1 C4 118.79(18) . . ?
C6 O2 C12 123.62(18) . . ?
C13 O5 C14 115.8(2) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 S1 126.31(19) . . ?
N1 C3 O1 109.9(2) . . ?
O1 C3 S1 123.71(17) . . ?
C5 C4 O1 120.3(2) . . ?
C5 C4 C9 122.4(2) . . ?
C9 C4 O1 117.1(2) . . ?
C4 C5 H5 121.1 . . ?
C4 C5 C6 117.8(2) . . ?
C6 C5 H5 121.1 . . ?
O2 C6 C5 117.55(19) . . ?
O2 C6 C7 120.2(2) . . ?
C5 C6 C7 122.3(2) . . ?
C6 C7 C8 117.7(2) . . ?
C6 C7 C10 117.5(2) . . ?
C8 C7 C10 124.7(2) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.8(2) . . ?
C9 C8 H8 119.6 . . ?
C4 C9 H9 120.5 . . ?
C8 C9 C4 119.0(2) . . ?
C8 C9 H9 120.5 . . ?
C7 C10 H10 118.7 . . ?
C11 C10 C7 122.7(2) . . ?
C11 C10 H10 118.7 . . ?
C10 C11 C12 119.8(2) . . ?
C10 C11 C13 118.0(2) . . ?
C12 C11 C13 122.2(2) . . ?
O2 C12 C11 116.1(2) . . ?
O3 C12 O2 115.6(2) . . ?
O3 C12 C11 128.2(2) . . ?
O4 C13 O5 123.5(2) . . ?
O4 C13 C11 122.0(2) . . ?
O5 C13 C11 114.5(2) . . ?
O5 C14 H14A 110.3 . . ?
O5 C14 H14B 110.3 . . ?
O5 C14 C15 107.0(2) . . ?
H14A C14 H14B 108.6 . . ?
C15 C14 H14A 110.3 . . ?
C15 C14 H14B 110.3 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C4 C5 C6 -177.5(2) . . . . ?
O1 C4 C9 C8 177.1(2) . . . . ?
O2 C6 C7 C8 -179.1(2) . . . . ?
O2 C6 C7 C10 3.1(3) . . . . ?
C1 N1 C3 S1 6.6(3) . . . . ?
C1 N1 C3 O1 -176.10(19) . . . . ?
C2 N1 C3 S1 179.56(19) . . . . ?
C2 N1 C3 O1 -3.1(3) . . . . ?
C3 O1 C4 C5 -71.9(3) . . . . ?
C3 O1 C4 C9 113.4(2) . . . . ?
C4 O1 C3 S1 -9.7(3) . . . . ?
C4 O1 C3 N1 172.85(19) . . . . ?
C4 C5 C6 O2 -178.5(2) . . . . ?
C4 C5 C6 C7 1.1(4) . . . . ?
C5 C4 C9 C8 2.5(4) . . . . ?
C5 C6 C7 C8 1.3(4) . . . . ?
C5 C6 C7 C10 -176.5(2) . . . . ?
C6 O2 C12 O3 -178.7(3) . . . . ?
C6 O2 C12 C11 1.1(4) . . . . ?
C6 C7 C8 C9 -1.9(4) . . . . ?
C6 C7 C10 C11 -0.8(4) . . . . ?
C7 C8 C9 C4 0.0(4) . . . . ?
C7 C10 C11 C12 -1.3(4) . . . . ?
C7 C10 C11 C13 177.3(2) . . . . ?
C8 C7 C10 C11 -178.4(2) . . . . ?
C9 C4 C5 C6 -3.1(4) . . . . ?
C10 C7 C8 C9 175.8(2) . . . . ?
C10 C11 C12 O2 1.2(4) . . . . ?
C10 C11 C12 O3 -179.0(3) . . . . ?
C10 C11 C13 O4 -12.7(4) . . . . ?
C10 C11 C13 O5 165.5(2) . . . . ?
C12 O2 C6 C5 176.3(2) . . . . ?
C12 O2 C6 C7 -3.3(4) . . . . ?
C12 C11 C13 O4 165.9(3) . . . . ?
C12 C11 C13 O5 -15.9(4) . . . . ?
C13 O5 C14 C15 177.8(3) . . . . ?
C13 C11 C12 O2 -177.3(2) . . . . ?
C13 C11 C12 O3 2.4(5) . . . . ?
C14 O5 C13 O4 0.1(4) . . . . ?
C14 O5 C13 C11 -178.0(2) . . . . ?

_shelx_SHELXL_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xb1481_0m
_database_code_depnum_ccdc_archive 'CCDC 1863813'
_audit_update_record             
;
2018-08-24 deposited with the CCDC.	2019-03-04 downloaded from the CCDC.
;
_audit_creation_date             2018-06-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H14 N2 O2 S2'
_chemical_formula_sum            'C17 H14 N2 O2 S2'
_chemical_formula_weight         342.42
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3'
_space_group_name_Hall           '-R 3'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   28.700(4)
_cell_length_b                   28.700(4)
_cell_length_c                   11.8086(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     8423(3)
_cell_formula_units_Z            18
_cell_measurement_reflns_used    1937
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.287
_cell_measurement_theta_min      2.379
_shelx_estimated_absorpt_T_max   0.959
_shelx_estimated_absorpt_T_min   0.944
_exptl_absorpt_coefficient_mu    0.293
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6763
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0776 before and 0.0514 after correction. The Ratio of minimum to maximum transmission is 0.9074. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             3204
_exptl_crystal_size_max          0.199
_exptl_crystal_size_mid          0.187
_exptl_crystal_size_min          0.143
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0426
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            14319
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.092
_diffrn_reflns_theta_max         25.092
_diffrn_reflns_theta_min         2.379
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2108
_reflns_number_total             3327
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     210
_refine_ls_number_reflns         3327
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0780
_refine_ls_R_factor_gt           0.0468
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0579P)²+1.1133P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1087
_refine_ls_wR_factor_ref         0.1240
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C9(H9), C10(H10), C11(H11), C14(H14)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.88959(3) 0.12423(3) 0.15977(6) 0.0668(2) Uani 1 1 d . . . . .
S2 S 0.84797(3) 0.05045(3) -0.14232(7) 0.0864(3) Uani 1 1 d . . . . .
N1 N 0.80156(9) 0.08468(8) 0.27687(19) 0.0693(6) Uani 1 1 d . . . . .
N2 N 0.93120(9) 0.15138(11) -0.13098(19) 0.0798(7) Uani 1 1 d . . . . .
O1 O 0.85667(6) 0.13897(6) -0.05182(13) 0.0598(5) Uani 1 1 d . . . . .
O2 O 0.75792(8) 0.11378(8) -0.31533(18) 0.0934(7) Uani 1 1 d . . . . .
C1 C 0.89342(12) 0.11338(10) 0.3020(2) 0.0663(7) Uani 1 1 d . . . . .
C2 C 0.93789(14) 0.12321(13) 0.3667(3) 0.0880(9) Uani 1 1 d . . . . .
H2 H 0.9717 0.1373 0.3338 0.106 Uiso 1 1 calc R . . . .
C3 C 0.93059(16) 0.11160(14) 0.4802(3) 0.1008(11) Uani 1 1 d . . . . .
H3 H 0.9598 0.1176 0.5246 0.121 Uiso 1 1 calc R . . . .
C4 C 0.88045(18) 0.09118(13) 0.5297(3) 0.0988(11) Uani 1 1 d . . . . .
H4 H 0.8767 0.0839 0.6069 0.119 Uiso 1 1 calc R . . . .
C5 C 0.83593(15) 0.08142(11) 0.4670(3) 0.0878(10) Uani 1 1 d . . . . .
H5 H 0.8024 0.0679 0.5013 0.105 Uiso 1 1 calc R . . . .
C6 C 0.84225(12) 0.09233(10) 0.3505(2) 0.0680(7) Uani 1 1 d . . . . .
C7 C 0.82051(10) 0.09932(9) 0.1746(2) 0.0580(7) Uani 1 1 d . . . . .
C8 C 0.78459(10) 0.09334(9) 0.0791(2) 0.0564(6) Uani 1 1 d . . . . .
C9 C 0.72915(12) 0.06836(11) 0.0993(3) 0.0764(8) Uani 1 1 d . . . . .
H9 H 0.7160 0.0569 0.1720 0.092 Uiso 1 1 calc R . . . .
C10 C 0.69361(12) 0.06053(13) 0.0124(3) 0.0881(10) Uani 1 1 d . . . . .
H10 H 0.6569 0.0435 0.0272 0.106 Uiso 1 1 calc R . . . .
C11 C 0.71212(11) 0.07768(12) -0.0957(3) 0.0796(8) Uani 1 1 d . . . . .
H11 H 0.6877 0.0718 -0.1535 0.096 Uiso 1 1 calc R . . . .
C12 C 0.76667(10) 0.10362(9) -0.1195(2) 0.0608(7) Uani 1 1 d . . . . .
C13 C 0.80162(9) 0.11032(9) -0.0306(2) 0.0552(6) Uani 1 1 d . . . . .
C14 C 0.78607(12) 0.12351(11) -0.2336(3) 0.0729(8) Uani 1 1 d . . . . .
H14 H 0.8230 0.1453 -0.2436 0.087 Uiso 1 1 calc R . . . .
C15 C 0.88077(10) 0.11479(11) -0.1093(2) 0.0628(7) Uani 1 1 d . . . . .
C16 C 0.96693(13) 0.13574(19) -0.1871(3) 0.1356(16) Uani 1 1 d . . . . .
H16A H 0.9488 0.0973 -0.1946 0.203 Uiso 1 1 calc GR . . . .
H16B H 0.9989 0.1477 -0.1427 0.203 Uiso 1 1 calc GR . . . .
H16C H 0.9764 0.1520 -0.2608 0.203 Uiso 1 1 calc GR . . . .
C17 C 0.95558(12) 0.20832(13) -0.1003(3) 0.0967(11) Uani 1 1 d . . . . .
H17A H 0.9284 0.2151 -0.0710 0.145 Uiso 1 1 calc GR . . . .
H17B H 0.9716 0.2301 -0.1662 0.145 Uiso 1 1 calc GR . . . .
H17C H 0.9827 0.2170 -0.0437 0.145 Uiso 1 1 calc GR . . . .


_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 1.722(3) . ?
S1 C7 1.748(3) . ?
S2 C15 1.646(3) . ?
N1 C6 1.383(3) . ?
N1 C7 1.305(3) . ?
N2 C15 1.320(3) . ?
N2 C16 1.467(4) . ?
N2 C17 1.465(4) . ?
O1 C13 1.391(3) . ?
O1 C15 1.379(3) . ?
O2 C14 1.198(3) . ?
C1 C2 1.390(4) . ?
C1 C6 1.401(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.372(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.383(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.379(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.402(4) . ?
C7 C8 1.478(3) . ?
C8 C9 1.400(3) . ?
C8 C13 1.384(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.384(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.376(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.385(4) . ?
C12 C13 1.397(3) . ?
C12 C14 1.461(4) . ?
C14 H14 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C7 89.44(13) . . ?
C7 N1 C6 110.4(2) . . ?
C15 N2 C16 120.0(3) . . ?
C15 N2 C17 124.1(3) . . ?
C17 N2 C16 115.8(3) . . ?
C15 O1 C13 119.90(18) . . ?
C2 C1 S1 129.4(2) . . ?
C2 C1 C6 121.4(3) . . ?
C6 C1 S1 109.2(2) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 C1 118.3(3) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3 119.5 . . ?
C2 C3 C4 121.1(3) . . ?
C4 C3 H3 119.5 . . ?
C3 C4 H4 119.3 . . ?
C5 C4 C3 121.5(3) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 120.7 . . ?
C4 C5 C6 118.5(3) . . ?
C6 C5 H5 120.7 . . ?
N1 C6 C1 115.5(2) . . ?
N1 C6 C5 125.2(3) . . ?
C1 C6 C5 119.2(3) . . ?
N1 C7 S1 115.4(2) . . ?
N1 C7 C8 120.9(2) . . ?
C8 C7 S1 123.62(18) . . ?
C9 C8 C7 118.5(2) . . ?
C13 C8 C7 124.7(2) . . ?
C13 C8 C9 116.7(2) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 C8 120.9(3) . . ?
C10 C9 H9 119.5 . . ?
C9 C10 H10 119.7 . . ?
C11 C10 C9 120.6(3) . . ?
C11 C10 H10 119.7 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.7(3) . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C13 117.6(3) . . ?
C11 C12 C14 120.3(3) . . ?
C13 C12 C14 122.2(2) . . ?
O1 C13 C12 118.1(2) . . ?
C8 C13 O1 118.3(2) . . ?
C8 C13 C12 123.5(2) . . ?
O2 C14 C12 124.8(3) . . ?
O2 C14 H14 117.6 . . ?
C12 C14 H14 117.6 . . ?
N2 C15 S2 129.1(2) . . ?
N2 C15 O1 108.8(2) . . ?
O1 C15 S2 122.14(18) . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C1 C2 C3 179.2(2) . . . . ?
S1 C1 C6 N1 0.6(3) . . . . ?
S1 C1 C6 C5 -178.6(2) . . . . ?
S1 C7 C8 C9 174.24(19) . . . . ?
S1 C7 C8 C13 -5.2(3) . . . . ?
N1 C7 C8 C9 -4.1(4) . . . . ?
N1 C7 C8 C13 176.5(2) . . . . ?
C1 S1 C7 N1 0.8(2) . . . . ?
C1 S1 C7 C8 -177.6(2) . . . . ?
C1 C2 C3 C4 -0.7(5) . . . . ?
C2 C1 C6 N1 179.8(2) . . . . ?
C2 C1 C6 C5 0.6(4) . . . . ?
C2 C3 C4 C5 0.4(6) . . . . ?
C3 C4 C5 C6 0.4(5) . . . . ?
C4 C5 C6 N1 -180.0(3) . . . . ?
C4 C5 C6 C1 -0.9(4) . . . . ?
C6 N1 C7 S1 -0.6(3) . . . . ?
C6 N1 C7 C8 177.9(2) . . . . ?
C6 C1 C2 C3 0.2(4) . . . . ?
C7 S1 C1 C2 -179.8(3) . . . . ?
C7 S1 C1 C6 -0.73(19) . . . . ?
C7 N1 C6 C1 0.0(3) . . . . ?
C7 N1 C6 C5 179.1(2) . . . . ?
C7 C8 C9 C10 -178.4(3) . . . . ?
C7 C8 C13 O1 -5.5(3) . . . . ?
C7 C8 C13 C12 179.3(2) . . . . ?
C8 C9 C10 C11 -0.7(5) . . . . ?
C9 C8 C13 O1 175.1(2) . . . . ?
C9 C8 C13 C12 -0.1(4) . . . . ?
C9 C10 C11 C12 -0.7(5) . . . . ?
C10 C11 C12 C13 1.6(4) . . . . ?
C10 C11 C12 C14 -177.7(3) . . . . ?
C11 C12 C13 O1 -176.4(2) . . . . ?
C11 C12 C13 C8 -1.2(4) . . . . ?
C11 C12 C14 O2 -9.5(4) . . . . ?
C13 O1 C15 S2 -6.8(3) . . . . ?
C13 O1 C15 N2 172.6(2) . . . . ?
C13 C8 C9 C10 1.1(4) . . . . ?
C13 C12 C14 O2 171.3(3) . . . . ?
C14 C12 C13 O1 2.8(3) . . . . ?
C14 C12 C13 C8 178.1(2) . . . . ?
C15 O1 C13 C8 107.1(2) . . . . ?
C15 O1 C13 C12 -77.4(3) . . . . ?
C16 N2 C15 S2 -3.5(4) . . . . ?
C16 N2 C15 O1 177.1(3) . . . . ?
C17 N2 C15 S2 177.8(2) . . . . ?
C17 N2 C15 O1 -1.6(3) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.000 -0.688 456.1 149.9 ?
2 0.333 0.667 -0.862 456.1 149.9 ?
3 0.667 0.333 -0.195 456.1 149.9 ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xb1445_0m
_database_code_depnum_ccdc_archive 'CCDC 1863815'
_audit_update_record             
;
2018-08-24 deposited with the CCDC.	2019-03-04 downloaded from the CCDC.
;
_audit_creation_date             2018-06-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'I, C28 H27 N4 O S2'
_chemical_formula_sum            'C28 H27 I N4 O S2'
_chemical_formula_weight         626.55
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.4238(13)
_cell_length_b                   20.241(2)
_cell_length_c                   13.3064(14)
_cell_angle_alpha                90
_cell_angle_beta                 115.300(2)
_cell_angle_gamma                90
_cell_volume                     2781.7(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2197
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      18.75
_cell_measurement_theta_min      2.63
_shelx_estimated_absorpt_T_max   0.844
_shelx_estimated_absorpt_T_min   0.796
_exptl_absorpt_coefficient_mu    1.329
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0943 before and 0.0464 after correction. The Ratio of minimum to maximum transmission is 0.8727. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.132
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_av_unetI/netI     0.0602
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            13959
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.100
_diffrn_reflns_theta_max         25.100
_diffrn_reflns_theta_min         1.969
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3012
_reflns_number_total             4944
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         1.128
_refine_diff_density_min         -0.803
_refine_diff_density_rms         0.100
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     325
_refine_ls_number_reflns         4944
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0505
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0809P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1276
_refine_ls_wR_factor_ref         0.1571
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Me refined with riding coordinates:
 C7(H7A,H7B,H7C), C8(H8A,H8B,H8C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C),
 C21(H21A,H21B,H21C)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C10(H10), C11(H11), C13(H13), C15(H15),
 C24(H24), C25(H25), C26(H26), C27(H27)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.58939(5) 0.39621(2) 0.36912(4) 0.0778(2) Uani 1 1 d . . . . .
S1 S 1.12816(15) 0.11117(7) 0.31469(14) 0.0620(4) Uani 1 1 d . . . . .
S2 S 0.87714(17) 0.13031(9) 0.43935(14) 0.0654(5) Uani 1 1 d . . . . .
N1 N 0.3662(4) 0.1397(2) 0.1138(4) 0.0501(12) Uani 1 1 d . . . . .
N2 N 0.2920(4) 0.2393(2) 0.1100(3) 0.0433(11) Uani 1 1 d . . . . .
N3 N 0.8124(5) 0.0379(2) 0.2819(4) 0.0594(13) Uani 1 1 d . . . . .
N4 N 1.2234(4) 0.2294(2) 0.3401(4) 0.0529(12) Uani 1 1 d . . . . .
O1 O 0.8622(3) 0.13389(17) 0.2338(3) 0.0485(9) Uani 1 1 d . . . . .
C1 C 0.1508(7) 0.0796(3) 0.0478(5) 0.0658(17) Uani 1 1 d . . . . .
H1 H 0.1812 0.0369 0.0487 0.079 Uiso 1 1 calc R . . . .
C2 C 0.0229(7) 0.0923(4) 0.0169(6) 0.075(2) Uani 1 1 d . . . . .
H2 H -0.0347 0.0570 -0.0017 0.090 Uiso 1 1 calc R . . . .
C3 C -0.0247(6) 0.1555(4) 0.0121(5) 0.0699(19) Uani 1 1 d . . . . .
H3 H -0.1132 0.1616 -0.0114 0.084 Uiso 1 1 calc R . . . .
C4 C 0.0557(5) 0.2097(3) 0.0411(4) 0.0550(15) Uani 1 1 d . . . . .
H4 H 0.0241 0.2524 0.0384 0.066 Uiso 1 1 calc R . . . .
C5 C 0.1870(5) 0.1973(3) 0.0749(4) 0.0457(13) Uani 1 1 d . . . . .
C6 C 0.2341(5) 0.1341(3) 0.0782(4) 0.0479(14) Uani 1 1 d . . . . .
C7 C 0.4532(6) 0.0826(3) 0.1295(6) 0.071(2) Uani 1 1 d . . . . .
H7A H 0.4030 0.0427 0.1094 0.107 Uiso 1 1 calc R . . . .
H7B H 0.4981 0.0878 0.0833 0.107 Uiso 1 1 calc R . . . .
H7C H 0.5149 0.0802 0.2060 0.107 Uiso 1 1 calc R . . . .
C8 C 0.2856(6) 0.3108(2) 0.1207(5) 0.0552(15) Uani 1 1 d . . . . .
H8A H 0.1973 0.3239 0.0990 0.083 Uiso 1 1 calc R . . . .
H8B H 0.3369 0.3235 0.1966 0.083 Uiso 1 1 calc R . . . .
H8C H 0.3184 0.3322 0.0736 0.083 Uiso 1 1 calc R . . . .
C9 C 0.4011(5) 0.2032(2) 0.1332(4) 0.0423(13) Uani 1 1 d . . . . .
C10 C 0.5281(5) 0.2322(3) 0.1728(4) 0.0491(14) Uani 1 1 d . . . . .
H10 H 0.5388 0.2737 0.2057 0.059 Uiso 1 1 calc R . . . .
C11 C 0.6304(5) 0.2061(3) 0.1670(5) 0.0520(15) Uani 1 1 d . . . . .
H11 H 0.6224 0.1639 0.1369 0.062 Uiso 1 1 calc R . . . .
C12 C 0.7568(5) 0.2393(3) 0.2051(4) 0.0470(13) Uani 1 1 d . . . . .
C13 C 0.7642(5) 0.3070(3) 0.2015(4) 0.0494(14) Uani 1 1 d . . . . .
H13 H 0.6886 0.3317 0.1794 0.059 Uiso 1 1 calc R . . . .
C14 C 0.8814(6) 0.3399(3) 0.2299(4) 0.0493(14) Uani 1 1 d . . . . .
C15 C 0.9914(5) 0.3021(3) 0.2634(4) 0.0496(14) Uani 1 1 d . . . . .
H15 H 1.0701 0.3233 0.2814 0.059 Uiso 1 1 calc R . . . .
C16 C 0.9904(5) 0.2330(3) 0.2715(4) 0.0463(13) Uani 1 1 d . . . . .
C17 C 0.8706(5) 0.2027(2) 0.2403(4) 0.0440(13) Uani 1 1 d . . . . .
C18 C 0.8839(6) 0.4140(3) 0.2209(6) 0.0661(17) Uani 1 1 d . . . . .
H18A H 0.7976 0.4310 0.1962 0.099 Uiso 1 1 calc R . . . .
H18B H 0.9382 0.4324 0.2922 0.099 Uiso 1 1 calc R . . . .
H18C H 0.9175 0.4258 0.1683 0.099 Uiso 1 1 calc R . . . .
C19 C 0.8488(5) 0.0987(3) 0.3160(5) 0.0502(14) Uani 1 1 d . . . . .
C20 C 0.7841(7) 0.0149(3) 0.1692(6) 0.087(2) Uani 1 1 d . . . . .
H20A H 0.7594 -0.0308 0.1622 0.130 Uiso 1 1 calc R . . . .
H20B H 0.7146 0.0405 0.1160 0.130 Uiso 1 1 calc R . . . .
H20C H 0.8598 0.0198 0.1559 0.130 Uiso 1 1 calc R . . . .
C21 C 0.8008(8) -0.0122(3) 0.3579(7) 0.087(2) Uani 1 1 d . . . . .
H21A H 0.7734 -0.0534 0.3191 0.130 Uiso 1 1 calc R . . . .
H21B H 0.8833 -0.0180 0.4202 0.130 Uiso 1 1 calc R . . . .
H21C H 0.7384 0.0022 0.3837 0.130 Uiso 1 1 calc R . . . .
C22 C 1.1147(5) 0.1975(3) 0.3088(4) 0.0490(14) Uani 1 1 d . . . . .
C23 C 1.3269(6) 0.1861(3) 0.3695(4) 0.0582(16) Uani 1 1 d . . . . .
C24 C 1.4561(6) 0.2039(4) 0.4032(5) 0.0667(18) Uani 1 1 d . . . . .
H24 H 1.4802 0.2481 0.4093 0.080 Uiso 1 1 calc R . . . .
C25 C 1.5469(7) 0.1548(5) 0.4271(6) 0.084(2) Uani 1 1 d . . . . .
H25 H 1.6332 0.1663 0.4492 0.101 Uiso 1 1 calc R . . . .
C26 C 1.5140(7) 0.0893(5) 0.4194(7) 0.093(3) Uani 1 1 d . . . . .
H26 H 1.5784 0.0575 0.4367 0.112 Uiso 1 1 calc R . . . .
C27 C 1.3878(7) 0.0696(4) 0.3866(6) 0.086(2) Uani 1 1 d . . . . .
H27 H 1.3665 0.0251 0.3828 0.103 Uiso 1 1 calc R . . . .
C28 C 1.2923(6) 0.1185(3) 0.3593(5) 0.0640(18) 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 C22 1.752(6) . ?
S1 C28 1.714(6) . ?
S2 C19 1.660(6) . ?
N1 C6 1.380(7) . ?
N1 C7 1.481(7) . ?
N1 C9 1.337(6) . ?
N2 C5 1.379(6) . ?
N2 C8 1.460(6) . ?
N2 C9 1.361(6) . ?
N3 C19 1.315(7) . ?
N3 C20 1.468(8) . ?
N3 C21 1.477(8) . ?
N4 C22 1.301(7) . ?
N4 C23 1.387(7) . ?
O1 C17 1.396(6) . ?
O1 C19 1.367(7) . ?
C1 H1 0.9300 . ?
C1 C2 1.363(9) . ?
C1 C6 1.399(8) . ?
C2 H2 0.9300 . ?
C2 C3 1.380(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.377(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.392(8) . ?
C5 C6 1.381(7) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.440(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.315(8) . ?
C11 H11 0.9300 . ?
C11 C12 1.474(7) . ?
C12 C13 1.375(7) . ?
C12 C17 1.392(7) . ?
C13 H13 0.9300 . ?
C13 C14 1.395(8) . ?
C14 C15 1.372(8) . ?
C14 C18 1.506(8) . ?
C15 H15 0.9300 . ?
C15 C16 1.404(7) . ?
C16 C17 1.391(7) . ?
C16 C22 1.475(7) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C23 C24 1.394(8) . ?
C23 C28 1.415(8) . ?
C24 H24 0.9300 . ?
C24 C25 1.372(9) . ?
C25 H25 0.9300 . ?
C25 C26 1.369(10) . ?
C26 H26 0.9300 . ?
C26 C27 1.375(10) . ?
C27 H27 0.9300 . ?
C27 C28 1.401(9) . ?

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
C28 S1 C22 89.5(3) . . ?
C6 N1 C7 123.6(5) . . ?
C9 N1 C6 109.7(4) . . ?
C9 N1 C7 126.7(5) . . ?
C5 N2 C8 124.8(5) . . ?
C9 N2 C5 109.0(4) . . ?
C9 N2 C8 126.1(4) . . ?
C19 N3 C20 123.2(5) . . ?
C19 N3 C21 120.9(5) . . ?
C20 N3 C21 115.8(5) . . ?
C22 N4 C23 111.0(5) . . ?
C19 O1 C17 119.9(4) . . ?
C2 C1 H1 121.7 . . ?
C2 C1 C6 116.5(6) . . ?
C6 C1 H1 121.7 . . ?
C1 C2 H2 118.7 . . ?
C1 C2 C3 122.6(6) . . ?
C3 C2 H2 118.7 . . ?
C2 C3 H3 119.2 . . ?
C4 C3 C2 121.6(6) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 121.8 . . ?
C3 C4 C5 116.4(6) . . ?
C5 C4 H4 121.8 . . ?
N2 C5 C4 131.3(5) . . ?
N2 C5 C6 106.8(5) . . ?
C6 C5 C4 121.9(5) . . ?
N1 C6 C1 132.3(5) . . ?
N1 C6 C5 106.8(5) . . ?
C5 C6 C1 120.9(6) . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 H8A 109.5 . . ?
N2 C8 H8B 109.5 . . ?
N2 C8 H8C 109.5 . . ?
H8A C8 H8B 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 N2 107.7(4) . . ?
N1 C9 C10 129.3(5) . . ?
N2 C9 C10 123.1(5) . . ?
C9 C10 H10 116.7 . . ?
C11 C10 C9 126.6(5) . . ?
C11 C10 H10 116.7 . . ?
C10 C11 H11 117.9 . . ?
C10 C11 C12 124.1(5) . . ?
C12 C11 H11 117.9 . . ?
C13 C12 C11 120.6(5) . . ?
C13 C12 C17 118.7(5) . . ?
C17 C12 C11 120.6(5) . . ?
C12 C13 H13 119.0 . . ?
C12 C13 C14 122.1(5) . . ?
C14 C13 H13 119.0 . . ?
C13 C14 C18 120.1(5) . . ?
C15 C14 C13 117.6(5) . . ?
C15 C14 C18 122.3(5) . . ?
C14 C15 H15 118.5 . . ?
C14 C15 C16 122.9(5) . . ?
C16 C15 H15 118.5 . . ?
C15 C16 C22 118.2(5) . . ?
C17 C16 C15 117.1(5) . . ?
C17 C16 C22 124.6(5) . . ?
C12 C17 O1 118.7(5) . . ?
C16 C17 O1 119.4(5) . . ?
C16 C17 C12 121.5(5) . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N3 C19 S2 126.9(5) . . ?
N3 C19 O1 109.8(5) . . ?
O1 C19 S2 123.2(4) . . ?
N3 C20 H20A 109.5 . . ?
N3 C20 H20B 109.5 . . ?
N3 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N3 C21 H21A 109.5 . . ?
N3 C21 H21B 109.5 . . ?
N3 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N4 C22 S1 115.3(4) . . ?
N4 C22 C16 121.0(5) . . ?
C16 C22 S1 123.7(4) . . ?
N4 C23 C24 125.9(6) . . ?
N4 C23 C28 114.5(5) . . ?
C24 C23 C28 119.6(6) . . ?
C23 C24 H24 120.7 . . ?
C25 C24 C23 118.7(7) . . ?
C25 C24 H24 120.7 . . ?
C24 C25 H25 119.1 . . ?
C26 C25 C24 121.8(7) . . ?
C26 C25 H25 119.1 . . ?
C25 C26 H26 119.3 . . ?
C25 C26 C27 121.4(7) . . ?
C27 C26 H26 119.3 . . ?
C26 C27 H27 120.9 . . ?
C26 C27 C28 118.2(7) . . ?
C28 C27 H27 120.9 . . ?
C23 C28 S1 109.7(5) . . ?
C27 C28 S1 130.1(6) . . ?
C27 C28 C23 120.2(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C9 C10 C11 21.9(10) . . . . ?
N2 C5 C6 N1 -0.8(6) . . . . ?
N2 C5 C6 C1 179.5(5) . . . . ?
N2 C9 C10 C11 -158.9(5) . . . . ?
N4 C23 C24 C25 -178.5(6) . . . . ?
N4 C23 C28 S1 -1.1(7) . . . . ?
N4 C23 C28 C27 -179.9(6) . . . . ?
C1 C2 C3 C4 -1.6(11) . . . . ?
C2 C1 C6 N1 179.5(6) . . . . ?
C2 C1 C6 C5 -0.9(9) . . . . ?
C2 C3 C4 C5 0.4(9) . . . . ?
C3 C4 C5 N2 -179.2(5) . . . . ?
C3 C4 C5 C6 0.6(8) . . . . ?
C4 C5 C6 N1 179.4(5) . . . . ?
C4 C5 C6 C1 -0.3(9) . . . . ?
C5 N2 C9 N1 -0.3(6) . . . . ?
C5 N2 C9 C10 -179.6(5) . . . . ?
C6 N1 C9 N2 -0.2(6) . . . . ?
C6 N1 C9 C10 179.0(5) . . . . ?
C6 C1 C2 C3 1.8(10) . . . . ?
C7 N1 C6 C1 -1.0(10) . . . . ?
C7 N1 C6 C5 179.4(5) . . . . ?
C7 N1 C9 N2 -179.0(5) . . . . ?
C7 N1 C9 C10 0.3(9) . . . . ?
C8 N2 C5 C4 0.8(9) . . . . ?
C8 N2 C5 C6 -179.0(5) . . . . ?
C8 N2 C9 N1 179.3(5) . . . . ?
C8 N2 C9 C10 0.0(8) . . . . ?
C9 N1 C6 C1 -179.7(6) . . . . ?
C9 N1 C6 C5 0.6(6) . . . . ?
C9 N2 C5 C4 -179.6(5) . . . . ?
C9 N2 C5 C6 0.6(6) . . . . ?
C9 C10 C11 C12 177.5(5) . . . . ?
C10 C11 C12 C13 -30.2(9) . . . . ?
C10 C11 C12 C17 152.9(6) . . . . ?
C11 C12 C13 C14 -175.7(5) . . . . ?
C11 C12 C17 O1 3.1(8) . . . . ?
C11 C12 C17 C16 176.9(5) . . . . ?
C12 C13 C14 C15 -0.7(8) . . . . ?
C12 C13 C14 C18 177.9(5) . . . . ?
C13 C12 C17 O1 -173.9(5) . . . . ?
C13 C12 C17 C16 -0.1(8) . . . . ?
C13 C14 C15 C16 -1.0(8) . . . . ?
C14 C15 C16 C17 2.1(8) . . . . ?
C14 C15 C16 C22 -179.8(5) . . . . ?
C15 C16 C17 O1 172.2(5) . . . . ?
C15 C16 C17 C12 -1.5(8) . . . . ?
C15 C16 C22 S1 -175.7(4) . . . . ?
C15 C16 C22 N4 4.4(8) . . . . ?
C17 O1 C19 S2 -15.4(7) . . . . ?
C17 O1 C19 N3 165.2(4) . . . . ?
C17 C12 C13 C14 1.3(8) . . . . ?
C17 C16 C22 S1 2.1(8) . . . . ?
C17 C16 C22 N4 -177.8(5) . . . . ?
C18 C14 C15 C16 -179.6(5) . . . . ?
C19 O1 C17 C12 -82.4(6) . . . . ?
C19 O1 C17 C16 103.6(6) . . . . ?
C20 N3 C19 S2 177.3(5) . . . . ?
C20 N3 C19 O1 -3.3(8) . . . . ?
C21 N3 C19 S2 -4.3(8) . . . . ?
C21 N3 C19 O1 175.1(5) . . . . ?
C22 S1 C28 C23 1.4(5) . . . . ?
C22 S1 C28 C27 180.0(7) . . . . ?
C22 N4 C23 C24 177.7(5) . . . . ?
C22 N4 C23 C28 0.0(7) . . . . ?
C22 C16 C17 O1 -5.7(8) . . . . ?
C22 C16 C17 C12 -179.4(5) . . . . ?
C23 N4 C22 S1 1.2(6) . . . . ?
C23 N4 C22 C16 -178.9(5) . . . . ?
C23 C24 C25 C26 -0.4(10) . . . . ?
C24 C23 C28 S1 -179.0(4) . . . . ?
C24 C23 C28 C27 2.3(10) . . . . ?
C24 C25 C26 C27 0.3(12) . . . . ?
C25 C26 C27 C28 1.0(12) . . . . ?
C26 C27 C28 S1 179.3(6) . . . . ?
C26 C27 C28 C23 -2.3(11) . . . . ?
C28 S1 C22 N4 -1.6(5) . . . . ?
C28 S1 C22 C16 178.5(5) . . . . ?
C28 C23 C24 C25 -0.9(9) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.310 0.139 0.883 8.9 3.1 ?
2 0.310 0.361 0.383 8.9 3.1 ?
3 0.690 0.639 0.617 8.9 2.9 ?
4 0.690 0.861 0.117 8.9 2.9 ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xb0602_0m
_database_code_depnum_ccdc_archive 'CCDC 1571173'
_audit_update_record             
;
2018-08-24 deposited with the CCDC.	2019-03-04 downloaded from the CCDC.
;
_audit_creation_date             2017-11-21
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H14 N2 O3 S2'
_chemical_formula_sum            'C19 H14 N2 O3 S2'
_chemical_formula_weight         382.44
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   6.515(8)
_cell_length_b                   11.778(16)
_cell_length_c                   22.99(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.01(4)
_cell_angle_gamma                90
_cell_volume                     1742(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    414
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      17.77
_cell_measurement_theta_min      2.49
_shelx_estimated_absorpt_T_max   0.958
_shelx_estimated_absorpt_T_min   0.892
_exptl_absorpt_coefficient_mu    0.328
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.5799
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0819 before and 0.0465 after correction.
The Ratio of minimum to maximum transmission is 0.7781.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.458
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.356
_exptl_crystal_size_mid          0.275
_exptl_crystal_size_min          0.133
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1577
_diffrn_reflns_av_unetI/netI     0.1945
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            8215
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.024
_diffrn_reflns_theta_max         25.024
_diffrn_reflns_theta_min         1.794
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1006
_reflns_number_total             3063
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.331
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.823
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         3063
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1968
_refine_ls_R_factor_gt           0.0629
_refine_ls_restrained_S_all      0.823
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0576P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1221
_refine_ls_wR_factor_ref         0.1693
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Me refined with riding coordinates:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C7(H7), C12(H12), C15(H15), C16(H16), C17(H17), C18(H18)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.6584(3) -0.00138(16) 0.21169(7) 0.0628(6) Uani 1 1 d . . . . .
S2 S 0.8207(3) 0.42873(17) -0.10829(7) 0.0596(6) Uani 1 1 d . . . . .
N1 N 0.6597(8) -0.2278(5) 0.2086(2) 0.0514(15) Uani 1 1 d . . . . .
N2 N 1.1707(8) 0.4205(5) -0.03769(19) 0.0473(14) Uani 1 1 d . . . . .
O1 O 0.8615(7) -0.1462(4) 0.15293(18) 0.0588(13) Uani 1 1 d . . . . .
O2 O 0.6079(7) 0.2412(4) -0.0738(2) 0.0769(16) Uani 1 1 d . . . . .
O3 O 0.6990(6) 0.1226(4) -0.00084(19) 0.0581(12) Uani 1 1 d . . . . .
C1 C 0.5029(10) -0.2325(6) 0.2468(3) 0.069(2) Uani 1 1 d . . . . .
H1A H 0.476134 -0.310243 0.255674 0.103 Uiso 1 1 calc R . . . .
H1B H 0.551484 -0.192391 0.282676 0.103 Uiso 1 1 calc R . . . .
H1C H 0.377113 -0.197918 0.227399 0.103 Uiso 1 1 calc R . . . .
C2 C 0.7318(11) -0.3358(6) 0.1877(3) 0.069(2) Uani 1 1 d . . . . .
H2A H 0.669036 -0.397384 0.205933 0.103 Uiso 1 1 calc R . . . .
H2B H 0.693382 -0.340544 0.145732 0.103 Uiso 1 1 calc R . . . .
H2C H 0.880194 -0.340465 0.197794 0.103 Uiso 1 1 calc R . . . .
C3 C 0.7230(9) -0.1288(6) 0.1902(2) 0.0517(18) Uani 1 1 d . . . . .
C4 C 0.7785(10) -0.0109(6) 0.0759(3) 0.0550(19) Uani 1 1 d . . . . .
H4 H 0.645893 -0.041497 0.066532 0.066 Uiso 1 1 calc R . . . .
C5 C 0.9156(11) -0.0521(6) 0.1211(3) 0.0488(17) Uani 1 1 d . . . . .
C6 C 1.1185(11) -0.0152(6) 0.1343(3) 0.062(2) Uani 1 1 d . . . . .
H6 H 1.211643 -0.048443 0.164264 0.074 Uiso 1 1 calc R . . . .
C7 C 1.1777(10) 0.0739(6) 0.1008(3) 0.0580(19) Uani 1 1 d . . . . .
H7 H 1.313488 0.100727 0.108911 0.070 Uiso 1 1 calc R . . . .
C8 C 1.0412(10) 0.1242(6) 0.0558(3) 0.0460(17) Uani 1 1 d . . . . .
C9 C 0.8419(10) 0.0785(6) 0.0439(3) 0.0489(17) Uani 1 1 d . . . . .
C10 C 0.7431(12) 0.2137(6) -0.0344(3) 0.0565(19) Uani 1 1 d . . . . .
C11 C 0.9469(10) 0.2644(6) -0.0204(3) 0.0467(17) Uani 1 1 d . . . . .
C12 C 1.0884(10) 0.2190(6) 0.0216(3) 0.0553(19) Uani 1 1 d . . . . .
H12 H 1.221113 0.250115 0.028751 0.066 Uiso 1 1 calc R . . . .
C13 C 0.9935(10) 0.3679(6) -0.0511(2) 0.0510(18) Uani 1 1 d . . . . .
C14 C 1.0016(9) 0.5331(6) -0.1142(3) 0.0494(18) Uani 1 1 d . . . . .
C15 C 0.9907(11) 0.6250(6) -0.1517(3) 0.0593(19) Uani 1 1 d . . . . .
H15 H 0.871298 0.637229 -0.178912 0.071 Uiso 1 1 calc R . . . .
C16 C 1.1528(13) 0.6975(7) -0.1491(3) 0.067(2) Uani 1 1 d . . . . .
H16 H 1.145882 0.758831 -0.174784 0.081 Uiso 1 1 calc R . . . .
C17 C 1.3301(11) 0.6798(6) -0.1078(3) 0.063(2) Uani 1 1 d . . . . .
H17 H 1.440542 0.730226 -0.106337 0.076 Uiso 1 1 calc R . . . .
C18 C 1.3469(10) 0.5900(6) -0.0692(3) 0.0548(19) Uani 1 1 d . . . . .
H18 H 1.465853 0.579331 -0.041635 0.066 Uiso 1 1 calc R . . . .
C19 C 1.1797(10) 0.5159(6) -0.0730(3) 0.0464(17) 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 C3 1.655(7) . ?
S2 C13 1.746(7) . ?
S2 C14 1.723(6) . ?
N1 C1 1.450(6) . ?
N1 C2 1.462(8) . ?
N1 C3 1.328(8) . ?
N2 C13 1.304(7) . ?
N2 C19 1.392(7) . ?
O1 C3 1.353(6) . ?
O1 C5 1.403(7) . ?
O2 C10 1.203(7) . ?
O3 C9 1.376(7) . ?
O3 C10 1.379(7) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C4 H4 0.9300 . ?
C4 C5 1.350(8) . ?
C4 C9 1.383(8) . ?
C5 C6 1.380(8) . ?
C6 H6 0.9300 . ?
C6 C7 1.391(8) . ?
C7 H7 0.9300 . ?
C7 C8 1.388(8) . ?
C8 C9 1.392(8) . ?
C8 C12 1.426(8) . ?
C10 C11 1.445(8) . ?
C11 C12 1.337(8) . ?
C11 C13 1.464(9) . ?
C12 H12 0.9300 . ?
C14 C15 1.378(8) . ?
C14 C19 1.393(8) . ?
C15 H15 0.9300 . ?
C15 C16 1.352(9) . ?
C16 H16 0.9300 . ?
C16 C17 1.390(9) . ?
C17 H17 0.9300 . ?
C17 C18 1.373(8) . ?
C18 H18 0.9300 . ?
C18 C19 1.388(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C14 S2 C13 89.1(3) . . ?
C1 N1 C2 117.3(6) . . ?
C3 N1 C1 120.7(6) . . ?
C3 N1 C2 121.9(5) . . ?
C13 N2 C19 111.3(5) . . ?
C3 O1 C5 117.2(5) . . ?
C9 O3 C10 122.4(5) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 S1 126.5(5) . . ?
N1 C3 O1 109.9(6) . . ?
O1 C3 S1 123.5(5) . . ?
C5 C4 H4 121.1 . . ?
C5 C4 C9 117.8(6) . . ?
C9 C4 H4 121.1 . . ?
C4 C5 O1 119.7(6) . . ?
C4 C5 C6 123.5(6) . . ?
C6 C5 O1 116.3(6) . . ?
C5 C6 H6 121.5 . . ?
C5 C6 C7 117.0(6) . . ?
C7 C6 H6 121.5 . . ?
C6 C7 H7 118.9 . . ?
C8 C7 C6 122.3(6) . . ?
C8 C7 H7 118.9 . . ?
C7 C8 C9 116.8(6) . . ?
C7 C8 C12 125.2(6) . . ?
C9 C8 C12 118.0(6) . . ?
O3 C9 C4 117.4(6) . . ?
O3 C9 C8 120.1(6) . . ?
C4 C9 C8 122.5(7) . . ?
O2 C10 O3 116.0(7) . . ?
O2 C10 C11 126.6(7) . . ?
O3 C10 C11 117.4(7) . . ?
C10 C11 C13 119.2(6) . . ?
C12 C11 C10 120.1(6) . . ?
C12 C11 C13 120.6(6) . . ?
C8 C12 H12 119.1 . . ?
C11 C12 C8 121.8(6) . . ?
C11 C12 H12 119.1 . . ?
N2 C13 S2 115.1(5) . . ?
N2 C13 C11 121.7(6) . . ?
C11 C13 S2 123.2(5) . . ?
C15 C14 S2 129.9(6) . . ?
C15 C14 C19 119.7(6) . . ?
C19 C14 S2 110.4(5) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 C14 120.3(7) . . ?
C16 C15 H15 119.8 . . ?
C15 C16 H16 120.2 . . ?
C15 C16 C17 119.7(7) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 119.0 . . ?
C18 C17 C16 122.0(7) . . ?
C18 C17 H17 119.0 . . ?
C17 C18 H18 121.3 . . ?
C17 C18 C19 117.5(6) . . ?
C19 C18 H18 121.3 . . ?
N2 C19 C14 114.0(6) . . ?
C18 C19 N2 125.1(6) . . ?
C18 C19 C14 120.8(6) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S2 C14 C15 C16 -179.8(5) . . . . ?
S2 C14 C19 N2 0.4(6) . . . . ?
S2 C14 C19 C18 -179.7(5) . . . . ?
O1 C5 C6 C7 176.5(5) . . . . ?
O2 C10 C11 C12 -174.4(7) . . . . ?
O2 C10 C11 C13 7.9(10) . . . . ?
O3 C10 C11 C12 3.6(9) . . . . ?
O3 C10 C11 C13 -174.2(5) . . . . ?
C1 N1 C3 S1 6.7(9) . . . . ?
C1 N1 C3 O1 -177.0(5) . . . . ?
C2 N1 C3 S1 -178.2(5) . . . . ?
C2 N1 C3 O1 -1.9(8) . . . . ?
C3 O1 C5 C4 -73.3(7) . . . . ?
C3 O1 C5 C6 113.7(6) . . . . ?
C4 C5 C6 C7 3.9(10) . . . . ?
C5 O1 C3 S1 -14.9(7) . . . . ?
C5 O1 C3 N1 168.7(5) . . . . ?
C5 C4 C9 O3 -177.9(5) . . . . ?
C5 C4 C9 C8 1.8(9) . . . . ?
C5 C6 C7 C8 -0.3(10) . . . . ?
C6 C7 C8 C9 -2.2(10) . . . . ?
C6 C7 C8 C12 176.9(6) . . . . ?
C7 C8 C9 O3 -178.8(5) . . . . ?
C7 C8 C9 C4 1.5(9) . . . . ?
C7 C8 C12 C11 -178.6(6) . . . . ?
C9 O3 C10 O2 177.1(6) . . . . ?
C9 O3 C10 C11 -1.1(9) . . . . ?
C9 C4 C5 O1 -177.0(5) . . . . ?
C9 C4 C5 C6 -4.6(10) . . . . ?
C9 C8 C12 C11 0.5(9) . . . . ?
C10 O3 C9 C4 178.1(6) . . . . ?
C10 O3 C9 C8 -1.7(9) . . . . ?
C10 C11 C12 C8 -3.3(9) . . . . ?
C10 C11 C13 S2 -4.9(8) . . . . ?
C10 C11 C13 N2 176.0(5) . . . . ?
C12 C8 C9 O3 2.0(9) . . . . ?
C12 C8 C9 C4 -177.7(6) . . . . ?
C12 C11 C13 S2 177.4(5) . . . . ?
C12 C11 C13 N2 -1.7(9) . . . . ?
C13 S2 C14 C15 -179.4(6) . . . . ?
C13 S2 C14 C19 -0.1(5) . . . . ?
C13 N2 C19 C14 -0.5(7) . . . . ?
C13 N2 C19 C18 179.5(6) . . . . ?
C13 C11 C12 C8 174.4(6) . . . . ?
C14 S2 C13 N2 -0.2(5) . . . . ?
C14 S2 C13 C11 -179.3(5) . . . . ?
C14 C15 C16 C17 -0.9(11) . . . . ?
C15 C14 C19 N2 179.8(5) . . . . ?
C15 C14 C19 C18 -0.3(9) . . . . ?
C15 C16 C17 C18 0.2(11) . . . . ?
C16 C17 C18 C19 0.4(10) . . . . ?
C17 C18 C19 N2 179.6(6) . . . . ?
C17 C18 C19 C14 -0.4(9) . . . . ?
C19 N2 C13 S2 0.4(7) . . . . ?
C19 N2 C13 C11 179.6(5) . . . . ?
C19 C14 C15 C16 0.9(10) . . . . ?

_shelx_SHELXL_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xb1277_sq_sq
_database_code_depnum_ccdc_archive 'CCDC 1863816'
_audit_update_record             
;
2018-08-24 deposited with the CCDC.	2019-03-04 downloaded from the CCDC.
;
_audit_creation_date             2018-04-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.04.03 svn.r3497 for OlexSys, GUI svn.r5486)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C25 H24 N3 O S2, I'
_chemical_formula_sum            'C25 H22 I N3 O S2'
_chemical_formula_weight         571.47
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.4772(13)
_cell_length_b                   20.032(2)
_cell_length_c                   20.904(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5643.6(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4357
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.47
_cell_measurement_theta_min      2.25
_shelx_estimated_absorpt_T_max   0.839
_shelx_estimated_absorpt_T_min   0.799
_exptl_absorpt_coefficient_mu    1.302
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6174
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0695 before and 0.0497 after correction. The Ratio of minimum to maximum transmission is 0.8284. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2288
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0512
_diffrn_reflns_av_unetI/netI     0.0420
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            29198
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.229
_diffrn_reflns_theta_min         1.948
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3619
_reflns_number_total             5662
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.826
_refine_diff_density_min         -0.745
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       0.00032(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         5662
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0843
_refine_ls_R_factor_gt           0.0535
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0616P)²+6.5151P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1346
_refine_ls_wR_factor_ref         0.1523
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C16(H16), C18(H18), C19(H19), C23(H23), C25(H25), C28(H28),
 C29(H29), C35(H35), C43(H43), C54(H54), C55(H55)
2.b Idealised Me refined as rotating group:
 C42(H42A,H42B,H42C), C47(H47A,H47B,H47C), C63(H63A,H63B,H63C), C67(H67A,H67B,
 H67C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S6 S 0.12609(8) 0.49998(5) 0.18135(5) 0.0484(3) Uani 1 1 d . . . . .
S1 S 0.34272(9) 0.45614(7) 0.02952(6) 0.0609(3) Uani 1 1 d . . . . .
O1 O 0.1710(2) 0.51808(13) 0.05075(12) 0.0457(7) Uani 1 1 d . . . . .
C7 C 0.1267(3) 0.4580(2) 0.03113(19) 0.0421(9) Uani 1 1 d . . . . .
C8 C 0.1167(3) 0.4204(2) 0.14641(19) 0.0422(9) Uani 1 1 d . . . . .
C11 C 0.1035(3) 0.4504(2) -0.03304(19) 0.0427(9) Uani 1 1 d . . . . .
C12 C 0.0423(3) 0.3392(2) -0.0085(2) 0.0516(11) Uani 1 1 d . . . . .
C13 C 0.1234(3) 0.5042(2) -0.07874(19) 0.0453(9) Uani 1 1 d . . . . .
H13 H 0.1403 0.5459 -0.0624 0.054 Uiso 1 1 calc R . . . .
C16 C 0.1175(3) 0.4930(2) 0.3159(2) 0.0566(11) Uani 1 1 d . . . . .
H16 H 0.1222 0.5391 0.3202 0.068 Uiso 1 1 calc R . . . .
C17 C 0.1304(3) 0.5508(2) -0.18873(19) 0.0452(10) Uani 1 1 d . . . . .
C18 C 0.0599(3) 0.3902(2) -0.0514(2) 0.0506(10) Uani 1 1 d . . . . .
H18 H 0.0422 0.3842 -0.0940 0.061 Uiso 1 1 calc R . . . .
C19 C 0.1031(3) 0.3843(3) 0.3625(2) 0.0622(12) Uani 1 1 d . . . . .
H19 H 0.0982 0.3582 0.3992 0.075 Uiso 1 1 calc R . . . .
C20 C 0.1185(3) 0.4631(2) 0.25573(18) 0.0454(10) Uani 1 1 d . . . . .
C23 C 0.1510(4) 0.6650(2) -0.2204(2) 0.0611(12) Uani 1 1 d . . . . .
H23 H 0.1587 0.7097 -0.2096 0.073 Uiso 1 1 calc R . . . .
N1 N 0.1100(2) 0.37052(19) 0.18639(16) 0.0502(9) Uani 1 1 d . . . . .
C25 C 0.1272(3) 0.5348(2) -0.25375(19) 0.0508(11) Uani 1 1 d . . . . .
H25 H 0.1185 0.4906 -0.2661 0.061 Uiso 1 1 calc R . . . .
C28 C 0.1039(3) 0.3539(2) 0.3035(2) 0.0568(11) Uani 1 1 d . . . . .
H28 H 0.0998 0.3077 0.3000 0.068 Uiso 1 1 calc R . . . .
C29 C 0.1417(3) 0.6177(2) -0.1734(2) 0.0536(11) Uani 1 1 d . . . . .
H29 H 0.1431 0.6307 -0.1307 0.064 Uiso 1 1 calc R . . . .
C30 C 0.2730(3) 0.5206(2) 0.05039(18) 0.0469(10) Uani 1 1 d . . . . .
C35 C 0.1191(3) 0.4977(2) -0.1419(2) 0.0473(10) Uani 1 1 d . . . . .
H35 H 0.1076 0.4550 -0.1577 0.057 Uiso 1 1 calc R . . . .
N2 N 0.3049(3) 0.5796(2) 0.0688(2) 0.0635(11) Uani 1 1 d . . . . .
C42 C 0.0008(4) 0.2730(3) -0.0302(3) 0.0734(15) Uani 1 1 d . . . . .
H42A H -0.0045 0.2728 -0.0760 0.110 Uiso 1 1 calc GR . . . .
H42B H -0.0636 0.2666 -0.0117 0.110 Uiso 1 1 calc GR . . . .
H42C H 0.0442 0.2377 -0.0167 0.110 Uiso 1 1 calc GR . . . .
C43 C 0.0634(3) 0.3506(2) 0.0560(2) 0.0480(10) Uani 1 1 d . . . . .
H43 H 0.0499 0.3172 0.0856 0.058 Uiso 1 1 calc R . . . .
C46 C 0.1040(3) 0.41017(19) 0.07705(19) 0.0406(9) Uani 1 1 d . . . . .
C47 C 0.2383(5) 0.6337(3) 0.0875(3) 0.096(2) Uani 1 1 d . . . . .
H47A H 0.2641 0.6555 0.1248 0.144 Uiso 1 1 calc GR . . . .
H47B H 0.1738 0.6158 0.0968 0.144 Uiso 1 1 calc GR . . . .
H47C H 0.2332 0.6653 0.0531 0.144 Uiso 1 1 calc GR . . . .
C53 C 0.1110(3) 0.3936(2) 0.24909(19) 0.0436(9) Uani 1 1 d . . . . .
C54 C 0.1364(3) 0.5825(2) -0.2988(2) 0.0536(11) Uani 1 1 d . . . . .
H54 H 0.1341 0.5707 -0.3418 0.064 Uiso 1 1 calc R . . . .
C55 C 0.1094(3) 0.4529(3) 0.3683(2) 0.0631(13) Uani 1 1 d . . . . .
H55 H 0.1081 0.4720 0.4088 0.076 Uiso 1 1 calc R . . . .
N0AA N 0.1488(3) 0.6464(2) -0.28269(18) 0.0584(10) Uani 1 1 d . . . . .
C63 C 0.1616(5) 0.6985(3) -0.3322(3) 0.0893(19) Uani 1 1 d . . . . .
H63A H 0.1157 0.7343 -0.3245 0.134 Uiso 1 1 calc GR . . . .
H63B H 0.1492 0.6797 -0.3737 0.134 Uiso 1 1 calc GR . . . .
H63C H 0.2282 0.7155 -0.3306 0.134 Uiso 1 1 calc GR . . . .
C67 C 0.4104(4) 0.5944(3) 0.0714(3) 0.095(2) Uani 1 1 d . . . . .
H67A H 0.4350 0.5853 0.1136 0.143 Uiso 1 1 calc GR . . . .
H67B H 0.4210 0.6406 0.0614 0.143 Uiso 1 1 calc GR . . . .
H67C H 0.4449 0.5670 0.0410 0.143 Uiso 1 1 calc GR . . . .
I0AA I 0.01893(4) 0.16336(2) 0.25282(2) 0.0930(2) 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
S6 C8 1.758(4) . ?
S6 C20 1.724(4) . ?
S1 C30 1.656(5) . ?
O1 C7 1.404(5) . ?
O1 C30 1.376(5) . ?
C7 C11 1.386(5) . ?
C7 C46 1.390(5) . ?
C8 N1 1.306(5) . ?
C8 C46 1.474(6) . ?
C11 C13 1.466(6) . ?
C11 C18 1.395(6) . ?
C12 C18 1.380(6) . ?
C12 C42 1.508(6) . ?
C12 C43 1.396(6) . ?
C13 C35 1.328(6) . ?
C16 C20 1.392(6) . ?
C16 C55 1.363(6) . ?
C17 C25 1.397(5) . ?
C17 C29 1.387(6) . ?
C17 C35 1.453(6) . ?
C19 C28 1.376(6) . ?
C19 C55 1.382(7) . ?
C20 C53 1.403(6) . ?
C23 C29 1.371(6) . ?
C23 N0AA 1.354(6) . ?
N1 C53 1.390(5) . ?
C25 C54 1.347(6) . ?
C28 C53 1.392(6) . ?
C30 N2 1.316(6) . ?
N2 C47 1.459(7) . ?
N2 C67 1.454(6) . ?
C43 C46 1.385(5) . ?
C54 N0AA 1.334(6) . ?
N0AA C63 1.480(6) . ?

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
C20 S6 C8 89.0(2) . . ?
C30 O1 C7 117.1(3) . . ?
C11 C7 O1 118.2(4) . . ?
C11 C7 C46 122.9(4) . . ?
C46 C7 O1 118.8(3) . . ?
N1 C8 S6 115.7(3) . . ?
N1 C8 C46 121.0(4) . . ?
C46 C8 S6 122.9(3) . . ?
C7 C11 C13 120.5(4) . . ?
C7 C11 C18 117.2(4) . . ?
C18 C11 C13 122.3(4) . . ?
C18 C12 C42 121.2(4) . . ?
C18 C12 C43 118.2(4) . . ?
C43 C12 C42 120.7(4) . . ?
C35 C13 C11 124.6(4) . . ?
C55 C16 C20 118.2(4) . . ?
C25 C17 C35 119.0(4) . . ?
C29 C17 C25 116.7(4) . . ?
C29 C17 C35 124.3(4) . . ?
C12 C18 C11 122.2(4) . . ?
C28 C19 C55 121.2(4) . . ?
C16 C20 S6 129.1(4) . . ?
C16 C20 C53 121.0(4) . . ?
C53 C20 S6 109.9(3) . . ?
N0AA C23 C29 119.9(4) . . ?
C8 N1 C53 110.3(4) . . ?
C54 C25 C17 121.0(4) . . ?
C19 C28 C53 118.7(4) . . ?
C23 C29 C17 120.8(4) . . ?
O1 C30 S1 122.7(3) . . ?
N2 C30 S1 126.3(4) . . ?
N2 C30 O1 111.0(4) . . ?
C13 C35 C17 126.4(4) . . ?
C30 N2 C47 123.0(4) . . ?
C30 N2 C67 120.9(5) . . ?
C67 N2 C47 116.1(4) . . ?
C46 C43 C12 121.9(4) . . ?
C7 C46 C8 123.9(4) . . ?
C43 C46 C7 117.5(4) . . ?
C43 C46 C8 118.6(4) . . ?
N1 C53 C20 115.1(4) . . ?
N1 C53 C28 125.4(4) . . ?
C28 C53 C20 119.5(4) . . ?
N0AA C54 C25 121.1(4) . . ?
C16 C55 C19 121.4(4) . . ?
C23 N0AA C63 118.5(5) . . ?
C54 N0AA C23 120.6(4) . . ?
C54 N0AA C63 121.0(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1863817'
_audit_update_record             
;
2018-08-24 deposited with the CCDC.	2019-03-04 downloaded from the CCDC.
;
_audit_creation_date             2018-06-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'I, C15 H16 N O'
_chemical_formula_sum            'C15 H16 I N O'
_chemical_formula_weight         353.19
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.2725(11)
_cell_length_b                   10.5716(17)
_cell_length_c                   10.5761(16)
_cell_angle_alpha                88.060(2)
_cell_angle_beta                 74.048(2)
_cell_angle_gamma                70.689(2)
_cell_volume                     736.4(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2057
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.110
_cell_measurement_theta_min      2.954
_shelx_estimated_absorpt_T_max   0.781
_shelx_estimated_absorpt_T_min   0.752
_exptl_absorpt_coefficient_mu    2.163
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.5954
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0983 before and 0.0262 after correction. The Ratio of minimum to maximum transmission is 0.7988. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0156
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.827
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4107
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.827
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.128
_diffrn_reflns_theta_min         2.045
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.827
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2583
_reflns_number_total             2982
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.745
_refine_diff_density_min         -0.537
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2982
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0319
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0388P)²+0.2551P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0764
_refine_ls_wR_factor_ref         0.0798
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C006(H006), C007(H007), C008(H008), C009(H009), C00A(H00A), C00B(H00B),
 C00D(H00D), C00F(H00F), C00G(H00G)
2.b Idealised Me refined as rotating group:
 C00H(H00C,H00E,H00H), C00I(H00I,H00J,H00K)
2.c Idealised tetrahedral OH refined as rotating group:
 O002(H002)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I001 I 0.35205(4) 0.81444(2) 0.75063(2) 0.05933(11) Uani 1 1 d . . . . .
O002 O 0.7182(4) 0.5658(3) 0.8230(3) 0.0644(7) Uani 1 1 d . . . . .
H002 H 0.628870 0.621989 0.798117 0.097 Uiso 1 1 calc GR . . . .
N003 N 0.7596(4) 0.7601(3) 0.1306(3) 0.0448(6) Uani 1 1 d . . . . .
C004 C 0.7580(5) 0.5817(3) 0.3278(3) 0.0398(7) Uani 1 1 d . . . . .
C005 C 0.7564(5) 0.4042(3) 0.6510(3) 0.0426(7) Uani 1 1 d . . . . .
C006 C 0.7587(5) 0.5017(3) 0.5504(3) 0.0431(7) Uani 1 1 d . . . . .
H006 H 0.760842 0.584670 0.575202 0.052 Uiso 1 1 calc R . . . .
C007 C 0.7429(5) 0.7140(3) 0.3530(3) 0.0444(7) Uani 1 1 d . . . . .
H007 H 0.731489 0.743723 0.437459 0.053 Uiso 1 1 calc R . . . .
C008 C 0.7581(5) 0.4840(3) 0.4264(3) 0.0451(7) Uani 1 1 d . . . . .
H008 H 0.757740 0.400716 0.401032 0.054 Uiso 1 1 calc R . . . .
C009 C 0.7702(5) 0.5455(3) 0.1987(3) 0.0440(7) Uani 1 1 d . . . . .
H009 H 0.777689 0.458801 0.178163 0.053 Uiso 1 1 calc R . . . .
C00A C 0.7450(5) 0.7998(3) 0.2537(3) 0.0483(8) Uani 1 1 d . . . . .
H00A H 0.736181 0.887557 0.271378 0.058 Uiso 1 1 calc R . . . .
C00B C 0.7742(5) 0.2713(4) 0.6211(3) 0.0489(8) Uani 1 1 d . . . . .
H00B H 0.785925 0.245969 0.535081 0.059 Uiso 1 1 calc R . . . .
C00C C 0.7339(5) 0.4404(4) 0.7833(3) 0.0481(8) Uani 1 1 d . . . . .
C00D C 0.7713(5) 0.6344(3) 0.1028(3) 0.0478(8) Uani 1 1 d . . . . .
H00D H 0.780268 0.608027 0.017707 0.057 Uiso 1 1 calc R . . . .
C00E C 0.7749(5) 0.1772(4) 0.7149(4) 0.0540(9) Uani 1 1 d . . . . .
C00F C 0.7354(6) 0.3463(4) 0.8769(4) 0.0563(9) Uani 1 1 d . . . . .
H00F H 0.722008 0.370861 0.963474 0.068 Uiso 1 1 calc R . . . .
C00G C 0.7563(6) 0.2184(4) 0.8443(4) 0.0593(10) Uani 1 1 d . . . . .
H00G H 0.758377 0.156448 0.908905 0.071 Uiso 1 1 calc R . . . .
C00H C 0.7952(7) 0.0361(4) 0.6788(5) 0.0751(12) Uani 1 1 d . . . . .
H00C H 0.770888 0.032765 0.594405 0.113 Uiso 1 1 calc GR . . . .
H00E H 0.698080 0.007938 0.744062 0.113 Uiso 1 1 calc GR . . . .
H00H H 0.929760 -0.022713 0.674704 0.113 Uiso 1 1 calc GR . . . .
C00I C 0.7625(7) 0.8537(4) 0.0227(4) 0.0670(11) Uani 1 1 d . . . . .
H00I H 0.706896 0.944619 0.059617 0.101 Uiso 1 1 calc GR . . . .
H00J H 0.682664 0.840541 -0.031226 0.101 Uiso 1 1 calc GR . . . .
H00K H 0.899714 0.836398 -0.030174 0.101 Uiso 1 1 calc GR . . . .


_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
O002 C00C 1.364(4) . ?
N003 C00A 1.346(4) . ?
N003 C00D 1.341(4) . ?
N003 C00I 1.486(4) . ?
C004 C007 1.395(4) . ?
C004 C008 1.443(4) . ?
C004 C009 1.402(4) . ?
C005 C006 1.457(4) . ?
C005 C00B 1.406(5) . ?
C005 C00C 1.414(4) . ?
C006 C008 1.332(4) . ?
C007 C00A 1.364(5) . ?
C009 C00D 1.359(5) . ?
C00B C00E 1.382(5) . ?
C00C C00F 1.379(5) . ?
C00E C00G 1.407(5) . ?
C00E C00H 1.502(6) . ?
C00F C00G 1.355(6) . ?

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
C00A N003 C00I 121.2(3) . . ?
C00D N003 C00A 120.5(3) . . ?
C00D N003 C00I 118.3(3) . . ?
C007 C004 C008 123.8(3) . . ?
C007 C004 C009 116.5(3) . . ?
C009 C004 C008 119.6(3) . . ?
C00B C005 C006 121.6(3) . . ?
C00B C005 C00C 117.4(3) . . ?
C00C C005 C006 121.0(3) . . ?
C008 C006 C005 126.5(3) . . ?
C00A C007 C004 120.0(3) . . ?
C006 C008 C004 126.2(3) . . ?
C00D C009 C004 121.4(3) . . ?
N003 C00A C007 121.4(3) . . ?
C00E C00B C005 122.3(3) . . ?
O002 C00C C005 122.4(3) . . ?
O002 C00C C00F 117.2(3) . . ?
C00F C00C C005 120.3(3) . . ?
N003 C00D C009 120.1(3) . . ?
C00B C00E C00G 117.7(4) . . ?
C00B C00E C00H 120.7(4) . . ?
C00G C00E C00H 121.7(4) . . ?
C00G C00F C00C 120.7(3) . . ?
C00F C00G C00E 121.5(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xb0783
_database_code_depnum_ccdc_archive 'CCDC 1586907'
_audit_update_record             
;
2018-08-24 deposited with the CCDC.	2019-03-04 downloaded from the CCDC.
;
_audit_creation_date             2017-11-21
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C19 H14 N2 O4 S'
_chemical_formula_sum            'C19 H14 N2 O4 S'
_chemical_formula_weight         366.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.087(2)
_cell_length_b                   9.953(3)
_cell_length_c                   12.356(5)
_cell_angle_alpha                111.892(6)
_cell_angle_beta                 94.737(6)
_cell_angle_gamma                110.387(4)
_cell_volume                     838.8(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1103
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      22.53
_cell_measurement_theta_min      2.77
_shelx_estimated_absorpt_T_max   0.967
_shelx_estimated_absorpt_T_min   0.923
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6587
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0721 before and 0.0376 after correction.
The Ratio of minimum to maximum transmission is 0.8838.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.451
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.368
_exptl_crystal_size_mid          0.276
_exptl_crystal_size_min          0.154
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0273
_diffrn_reflns_av_unetI/netI     0.0537
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4597
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.180
_diffrn_reflns_theta_min         2.771
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2136
_reflns_number_total             3261
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.190
_refine_diff_density_min         -0.214
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.027(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     257
_refine_ls_number_reflns         3261
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0493
_refine_ls_restrained_S_all      1.011
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0644P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1173
_refine_ls_wR_factor_ref         0.1359
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(O4A)=Sof(N2A)=1-FVAR(1)
 Sof(O4)=Sof(N2)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C9(H9), C12(H12), C15(H15), C16(H16), C17(H17), C18(H18)
3.b Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.44851(10) 0.64622(10) 0.45384(8) 0.0830(3) Uani 1 1 d . . . . .
N1 N 0.3561(3) 0.5826(2) 0.2224(2) 0.0684(6) Uani 1 1 d . . . . .
O4 O -0.113(4) 1.202(2) 0.9752(19) 0.052(3) Uani 0.52(2) 1 d . . P A 1
O1 O 0.2724(2) 0.75935(17) 0.34546(13) 0.0601(5) Uani 1 1 d . . . . .
O2 O 0.1682(2) 1.12059(17) 0.68004(13) 0.0545(4) Uani 1 1 d . . . . .
O3 O 0.1439(3) 1.2998(2) 0.84041(17) 0.0844(6) Uani 1 1 d . . . . .
N2 N -0.206(3) 0.957(3) 0.933(2) 0.051(4) Uani 0.52(2) 1 d . . P A 1
C1 C 0.2584(5) 0.5932(4) 0.1231(3) 0.0909(10) Uani 1 1 d . . . . .
H1A H 0.165673 0.628421 0.148131 0.136 Uiso 1 1 calc GR . . . .
H1B H 0.203338 0.490651 0.055726 0.136 Uiso 1 1 calc GR . . . .
H1C H 0.341975 0.667449 0.100292 0.136 Uiso 1 1 calc GR . . . .
C2 C 0.4520(5) 0.4785(4) 0.1903(4) 0.1186(14) Uani 1 1 d . . . . .
H2A H 0.542795 0.506961 0.259540 0.178 Uiso 1 1 calc GR . . . .
H2B H 0.509218 0.489835 0.127344 0.178 Uiso 1 1 calc GR . . . .
H2C H 0.366829 0.370323 0.163098 0.178 Uiso 1 1 calc GR . . . .
C3 C 0.3559(3) 0.6581(3) 0.3359(2) 0.0536(6) Uani 1 1 d . . . . .
C4 C 0.1773(3) 0.7866(3) 0.4350(2) 0.0497(6) Uani 1 1 d . . . . .
C5 C 0.0368(3) 0.6596(3) 0.4372(2) 0.0570(6) Uani 1 1 d . . . . .
H5 H 0.009644 0.556360 0.381937 0.068 Uiso 1 1 calc R . . . .
C6 C -0.0612(3) 0.6873(3) 0.5211(2) 0.0552(6) Uani 1 1 d . . . . .
H6 H -0.156864 0.602618 0.522149 0.066 Uiso 1 1 calc R . . . .
C7 C -0.0194(3) 0.8425(3) 0.60585(19) 0.0473(5) Uani 1 1 d . . . . .
C8 C 0.1196(3) 0.9663(2) 0.59844(19) 0.0446(5) Uani 1 1 d . . . . .
C9 C 0.2199(3) 0.9410(3) 0.51332(19) 0.0494(6) Uani 1 1 d . . . . .
H9 H 0.312490 1.025140 0.509304 0.059 Uiso 1 1 calc R . . . .
C10 C 0.0896(3) 1.1607(3) 0.7760(2) 0.0561(6) Uani 1 1 d . . . . .
C11 C -0.0490(3) 1.0301(3) 0.7884(2) 0.0511(6) Uani 1 1 d . . . . .
C12 C -0.1026(3) 0.8799(3) 0.7039(2) 0.0521(6) Uani 1 1 d . . . . .
H12 H -0.196537 0.798435 0.709873 0.063 Uiso 1 1 calc R . . . .
C13 C -0.1215(3) 1.0616(4) 0.8947(2) 0.0576(6) Uani 1 1 d . . . . .
C14 C -0.1919(3) 1.1779(3) 1.0566(2) 0.0577(6) Uani 1 1 d . . . . .
C15 C -0.2200(4) 1.2839(4) 1.1556(2) 0.0774(8) Uani 1 1 d . . . . .
H15 H -0.175103 1.391762 1.174770 0.093 Uiso 1 1 calc R . . . .
C16 C -0.3174(4) 1.2215(4) 1.2239(2) 0.0823(9) Uani 1 1 d . . . . .
H16 H -0.339209 1.288884 1.291376 0.099 Uiso 1 1 calc R . . . .
C17 C -0.3841(4) 1.0613(4) 1.1952(3) 0.0761(8) Uani 1 1 d . . . . .
H17 H -0.448292 1.023644 1.244388 0.091 Uiso 1 1 calc R . . . .
C18 C -0.3578(3) 0.9556(3) 1.0953(3) 0.0677(7) Uani 1 1 d . . . . .
H18 H -0.404115 0.847456 1.075090 0.081 Uiso 1 1 calc R . . . .
C19 C -0.2595(3) 1.0189(3) 1.0272(2) 0.0553(6) Uani 1 1 d . . . . .
O4A O -0.219(3) 0.933(3) 0.913(2) 0.053(4) Uani 0.48(2) 1 d . . P A 2
N2A N -0.086(5) 1.209(3) 0.965(3) 0.067(7) Uani 0.48(2) 1 d . . P A 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 C3 1.646(3) . ?
N1 C1 1.461(4) . ?
N1 C2 1.461(3) . ?
N1 C3 1.322(3) . ?
O4 C13 1.351(19) . ?
O4 C14 1.29(3) . ?
O1 C3 1.372(2) . ?
O1 C4 1.397(3) . ?
O2 C8 1.375(2) . ?
O2 C10 1.385(3) . ?
O3 C10 1.200(2) . ?
N2 C13 1.31(2) . ?
N2 C19 1.28(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C4 C5 1.386(3) . ?
C4 C9 1.372(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.361(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.403(3) . ?
C7 C8 1.388(3) . ?
C7 C12 1.425(3) . ?
C8 C9 1.383(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.460(3) . ?
C11 C12 1.350(3) . ?
C11 C13 1.454(3) . ?
C12 H12 0.9300 . ?
C13 O4A 1.364(19) . ?
C13 N2A 1.31(3) . ?
C14 C15 1.382(3) . ?
C14 C19 1.368(3) . ?
C14 N2A 1.53(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.371(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.381(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.381(4) . ?
C18 H18 0.9300 . ?
C18 C19 1.376(3) . ?
C19 O4A 1.49(2) . ?

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 N1 C2 116.6(3) . . ?
C3 N1 C1 123.0(2) . . ?
C3 N1 C2 120.4(3) . . ?
C14 O4 C13 108.5(15) . . ?
C3 O1 C4 117.94(17) . . ?
C8 O2 C10 122.78(18) . . ?
C19 N2 C13 111.7(15) . . ?
N1 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
N1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N1 C2 H2A 109.5 . . ?
N1 C2 H2B 109.5 . . ?
N1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 S1 127.49(19) . . ?
N1 C3 O1 110.0(2) . . ?
O1 C3 S1 122.42(18) . . ?
C5 C4 O1 119.5(2) . . ?
C9 C4 O1 118.0(2) . . ?
C9 C4 C5 122.3(2) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.4(2) . . ?
C6 C5 H5 120.3 . . ?
C5 C6 H6 119.7 . . ?
C5 C6 C7 120.6(2) . . ?
C7 C6 H6 119.7 . . ?
C6 C7 C12 123.9(2) . . ?
C8 C7 C6 118.0(2) . . ?
C8 C7 C12 117.9(2) . . ?
O2 C8 C7 120.55(19) . . ?
O2 C8 C9 117.06(19) . . ?
C9 C8 C7 122.3(2) . . ?
C4 C9 C8 117.3(2) . . ?
C4 C9 H9 121.4 . . ?
C8 C9 H9 121.4 . . ?
O2 C10 C11 116.8(2) . . ?
O3 C10 O2 116.1(2) . . ?
O3 C10 C11 127.1(2) . . ?
C12 C11 C10 119.7(2) . . ?
C12 C11 C13 120.4(2) . . ?
C13 C11 C10 119.8(2) . . ?
C7 C12 H12 119.0 . . ?
C11 C12 C7 122.0(2) . . ?
C11 C12 H12 119.0 . . ?
O4 C13 C11 128.4(12) . . ?
N2 C13 O4 105.7(15) . . ?
N2 C13 C11 125.9(10) . . ?
O4A C13 C11 116.2(10) . . ?
N2A C13 C11 118.3(16) . . ?
N2A C13 O4A 125.6(18) . . ?
O4 C14 C15 129.7(7) . . ?
O4 C14 C19 108.2(8) . . ?
C15 C14 N2A 129.4(11) . . ?
C19 C14 C15 121.9(3) . . ?
C19 C14 N2A 108.6(10) . . ?
C14 C15 H15 121.8 . . ?
C16 C15 C14 116.4(3) . . ?
C16 C15 H15 121.8 . . ?
C15 C16 H16 119.1 . . ?
C15 C16 C17 121.7(3) . . ?
C17 C16 H16 119.1 . . ?
C16 C17 H17 119.2 . . ?
C18 C17 C16 121.6(3) . . ?
C18 C17 H17 119.2 . . ?
C17 C18 H18 121.8 . . ?
C19 C18 C17 116.5(3) . . ?
C19 C18 H18 121.8 . . ?
N2 C19 C14 105.6(10) . . ?
N2 C19 C18 132.5(10) . . ?
C14 C19 C18 121.8(3) . . ?
C14 C19 O4A 110.3(8) . . ?
C18 C19 O4A 127.8(8) . . ?
C13 O4A C19 97.4(14) . . ?
C13 N2A C14 98(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 C14 C15 C16 177.0(12) . . . . ?
O4 C14 C19 N2 4.4(13) . . . . ?
O4 C14 C19 C18 -177.6(10) . . . . ?
O1 C4 C5 C6 -176.85(19) . . . . ?
O1 C4 C9 C8 177.46(18) . . . . ?
O2 C8 C9 C4 177.17(17) . . . . ?
O2 C10 C11 C12 -4.2(3) . . . . ?
O2 C10 C11 C13 172.64(19) . . . . ?
O3 C10 C11 C12 176.2(2) . . . . ?
O3 C10 C11 C13 -7.0(4) . . . . ?
C1 N1 C3 S1 175.53(19) . . . . ?
C1 N1 C3 O1 -7.6(3) . . . . ?
C2 N1 C3 S1 -2.4(4) . . . . ?
C2 N1 C3 O1 174.5(2) . . . . ?
C3 O1 C4 C5 -57.6(3) . . . . ?
C3 O1 C4 C9 126.6(2) . . . . ?
C4 O1 C3 S1 -34.9(3) . . . . ?
C4 O1 C3 N1 148.03(19) . . . . ?
C4 C5 C6 C7 -0.9(4) . . . . ?
C5 C4 C9 C8 1.8(3) . . . . ?
C5 C6 C7 C8 2.5(3) . . . . ?
C5 C6 C7 C12 -173.1(2) . . . . ?
C6 C7 C8 O2 -179.16(19) . . . . ?
C6 C7 C8 C9 -1.9(3) . . . . ?
C6 C7 C12 C11 175.1(2) . . . . ?
C7 C8 C9 C4 -0.2(3) . . . . ?
C8 O2 C10 O3 -179.8(2) . . . . ?
C8 O2 C10 C11 0.5(3) . . . . ?
C8 C7 C12 C11 -0.5(3) . . . . ?
C9 C4 C5 C6 -1.3(4) . . . . ?
C10 O2 C8 C7 3.3(3) . . . . ?
C10 O2 C8 C9 -174.15(19) . . . . ?
C10 C11 C12 C7 4.2(3) . . . . ?
C10 C11 C13 O4 17.5(12) . . . . ?
C10 C11 C13 N2 -160.4(11) . . . . ?
C10 C11 C13 O4A -166.0(9) . . . . ?
C10 C11 C13 N2A 12.8(14) . . . . ?
C11 C13 O4A C19 179.0(5) . . . . ?
C11 C13 N2A C14 178.7(6) . . . . ?
C12 C7 C8 O2 -3.3(3) . . . . ?
C12 C7 C8 C9 173.98(19) . . . . ?
C12 C11 C13 O4 -165.7(11) . . . . ?
C12 C11 C13 N2 16.4(12) . . . . ?
C12 C11 C13 O4A 10.8(9) . . . . ?
C12 C11 C13 N2A -170.4(14) . . . . ?
C13 O4 C14 C15 -178.7(5) . . . . ?
C13 O4 C14 C19 -2.1(15) . . . . ?
C13 N2 C19 C14 -5.1(16) . . . . ?
C13 N2 C19 C18 177.2(6) . . . . ?
C13 C11 C12 C7 -172.6(2) . . . . ?
C14 O4 C13 N2 -0.9(18) . . . . ?
C14 O4 C13 C11 -179.2(6) . . . . ?
C14 C15 C16 C17 -0.1(4) . . . . ?
C14 C19 O4A C13 2.6(12) . . . . ?
C15 C14 C19 N2 -178.7(10) . . . . ?
C15 C14 C19 C18 -0.7(4) . . . . ?
C15 C14 C19 O4A 176.5(8) . . . . ?
C15 C14 N2A C13 -176.9(6) . . . . ?
C15 C16 C17 C18 -0.8(4) . . . . ?
C16 C17 C18 C19 1.0(4) . . . . ?
C17 C18 C19 N2 177.2(13) . . . . ?
C17 C18 C19 C14 -0.2(4) . . . . ?
C17 C18 C19 O4A -176.9(9) . . . . ?
C18 C19 O4A C13 179.6(4) . . . . ?
C19 N2 C13 O4 3.8(19) . . . . ?
C19 N2 C13 C11 -177.8(7) . . . . ?
C19 C14 C15 C16 0.8(4) . . . . ?
C19 C14 N2A C13 3.9(17) . . . . ?
O4A C13 N2A C14 -3(2) . . . . ?
N2A C13 O4A C19 0(2) . . . . ?
N2A C14 C15 C16 -178.3(14) . . . . ?
N2A C14 C19 C18 178.6(11) . . . . ?
N2A C14 C19 O4A -4.3(14) . . . . ?

_shelx_SHELXL_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xb1387
_database_code_depnum_ccdc_archive 'CCDC 1863814'
_audit_update_record             
;
2018-08-24 deposited with the CCDC.	2019-03-04 downloaded from the CCDC.
;
_audit_creation_date             2018-06-20
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H16 N2 O2 S2'
_chemical_formula_sum            'C18 H16 N2 O2 S2'
_chemical_formula_weight         356.45
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.9911(19)
_cell_length_b                   16.171(3)
_cell_length_c                   11.1317(18)
_cell_angle_alpha                90
_cell_angle_beta                 117.048(3)
_cell_angle_gamma                90
_cell_volume                     1922.5(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1925
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.838
_cell_measurement_theta_min      2.285
_shelx_estimated_absorpt_T_max   0.963
_shelx_estimated_absorpt_T_min   0.955
_exptl_absorpt_coefficient_mu    0.288
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0838 before and 0.0466 after correction. The Ratio of minimum to maximum transmission is 0.8953. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             744
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.13
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_unetI/netI     0.0461
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10165
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.080
_diffrn_reflns_theta_min         1.907
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2449
_reflns_number_total             3784
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.257
_refine_diff_density_min         -0.176
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         3784
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0498
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0585P)²+0.1661P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1313
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C10(H10), C14(H14), C15(H15), C17(H17), C19(H19), C21(H21)
2.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.03222(6) 0.15666(4) 0.52478(7) 0.0617(2) Uani 1 1 d . . . . .
S2 S 0.22576(8) 0.20845(5) 0.32136(8) 0.0786(3) Uani 1 1 d . . . . .
O0AA O 0.22448(15) 0.08815(11) 0.48299(16) 0.0596(4) Uani 1 1 d . . . . .
N1 N -0.16413(19) 0.07890(13) 0.3526(2) 0.0586(5) Uani 1 1 d . . . . .
C3 C -0.0440(2) 0.08700(14) 0.3926(2) 0.0493(6) Uani 1 1 d . . . . .
C4 C 0.0197(2) 0.03982(14) 0.3277(2) 0.0498(6) Uani 1 1 d . . . . .
C5 C -0.0517(3) -0.01147(14) 0.2187(3) 0.0585(6) Uani 1 1 d . . . . .
H5 H -0.1376 -0.0148 0.1899 0.070 Uiso 1 1 calc R . . . .
C6 C 0.1475(2) 0.04354(14) 0.3678(2) 0.0514(6) Uani 1 1 d . . . . .
C7 C 0.0003(3) -0.05782(15) 0.1514(3) 0.0650(7) Uani 1 1 d . . . . .
C8 C 0.2033(3) -0.00176(16) 0.3033(3) 0.0633(7) Uani 1 1 d . . . . .
C9 C -0.2030(2) 0.13014(16) 0.4265(3) 0.0606(7) Uani 1 1 d . . . . .
C10 C 0.1276(3) -0.05192(16) 0.1961(3) 0.0718(8) Uani 1 1 d . . . . .
H10 H 0.1641 -0.0827 0.1526 0.086 Uiso 1 1 calc R . . . .
N2 N 0.3515(2) 0.19114(16) 0.5892(2) 0.0748(7) Uani 1 1 d . . . . .
C12 C 0.2710(2) 0.16366(17) 0.4695(3) 0.0590(7) Uani 1 1 d . . . . .
C13 C -0.1092(2) 0.17825(15) 0.5239(3) 0.0594(6) Uani 1 1 d . . . . .
C14 C -0.1349(3) 0.23320(19) 0.6051(3) 0.0817(9) Uani 1 1 d . . . . .
H14 H -0.0721 0.2654 0.6699 0.098 Uiso 1 1 calc R . . . .
C15 C -0.3510(3) 0.1891(2) 0.4896(4) 0.0939(10) Uani 1 1 d . . . . .
H15 H -0.4321 0.1928 0.4798 0.113 Uiso 1 1 calc R . . . .
C16 C -0.0818(3) -0.11390(18) 0.0362(3) 0.0937(10) Uani 1 1 d . . . . .
H16A H -0.0862 -0.1675 0.0709 0.140 Uiso 1 1 calc GR . . . .
H16B H -0.0469 -0.1190 -0.0259 0.140 Uiso 1 1 calc GR . . . .
H16C H -0.1644 -0.0908 -0.0096 0.140 Uiso 1 1 calc GR . . . .
C17 C -0.3258(3) 0.1357(2) 0.4095(3) 0.0817(9) Uani 1 1 d . . . . .
H17 H -0.3891 0.1036 0.3451 0.098 Uiso 1 1 calc R . . . .
C18 C 0.3890(3) 0.1418(2) 0.7132(3) 0.1049(12) Uani 1 1 d . . . . .
H18A H 0.3315 0.1518 0.7498 0.157 Uiso 1 1 calc GR . . . .
H18B H 0.4719 0.1574 0.7782 0.157 Uiso 1 1 calc GR . . . .
H18C H 0.3879 0.0841 0.6923 0.157 Uiso 1 1 calc GR . . . .
C19 C 0.3410(3) 0.0034(2) 0.3511(4) 0.0955(11) Uani 1 1 d . . . . .
H19 H 0.3893 0.0311 0.4314 0.115 Uiso 1 1 calc R . . . .
C20 C 0.4085(3) 0.2727(2) 0.6041(4) 0.1062(12) Uani 1 1 d . . . . .
H20A H 0.3864 0.2955 0.5165 0.159 Uiso 1 1 calc GR . . . .
H20B H 0.4979 0.2677 0.6534 0.159 Uiso 1 1 calc GR . . . .
H20C H 0.3787 0.3084 0.6522 0.159 Uiso 1 1 calc GR . . . .
C21 C -0.2569(3) 0.2378(2) 0.5854(4) 0.0965(11) Uani 1 1 d . . . . .
H21 H -0.2767 0.2742 0.6374 0.116 Uiso 1 1 calc R . . . .
O3 O 0.3921(3) -0.0258(2) 0.2925(3) 0.1570(12) 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 C3 1.745(2) . ?
S1 C13 1.727(3) . ?
S2 C12 1.651(3) . ?
O0AA C6 1.393(3) . ?
O0AA C12 1.379(3) . ?
N1 C3 1.307(3) . ?
N1 C9 1.389(3) . ?
C3 C4 1.480(3) . ?
C4 C5 1.396(3) . ?
C4 C6 1.388(3) . ?
C5 C7 1.392(3) . ?
C6 C8 1.392(3) . ?
C7 C10 1.377(4) . ?
C7 C16 1.513(4) . ?
C8 C10 1.387(4) . ?
C8 C19 1.489(4) . ?
C9 C13 1.392(4) . ?
C9 C17 1.400(3) . ?
N2 C12 1.317(3) . ?
N2 C18 1.477(4) . ?
N2 C20 1.460(4) . ?
C13 C14 1.398(3) . ?
C14 C21 1.379(4) . ?
C15 C17 1.370(4) . ?
C15 C21 1.392(5) . ?
C19 O3 1.177(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
C13 S1 C3 89.40(12) . . ?
C12 O0AA C6 119.36(18) . . ?
C3 N1 C9 110.7(2) . . ?
N1 C3 S1 115.19(17) . . ?
N1 C3 C4 121.1(2) . . ?
C4 C3 S1 123.76(18) . . ?
C5 C4 C3 118.8(2) . . ?
C6 C4 C3 124.0(2) . . ?
C6 C4 C5 117.2(2) . . ?
C7 C5 C4 122.6(2) . . ?
C4 C6 O0AA 119.4(2) . . ?
C4 C6 C8 122.0(2) . . ?
C8 C6 O0AA 118.3(2) . . ?
C5 C7 C16 120.1(3) . . ?
C10 C7 C5 117.6(2) . . ?
C10 C7 C16 122.3(3) . . ?
C6 C8 C19 120.2(3) . . ?
C10 C8 C6 118.1(2) . . ?
C10 C8 C19 121.7(2) . . ?
N1 C9 C17 125.0(3) . . ?
C13 C9 N1 115.2(2) . . ?
C13 C9 C17 119.8(3) . . ?
C7 C10 C8 122.4(2) . . ?
C12 N2 C18 122.3(3) . . ?
C12 N2 C20 120.7(3) . . ?
C20 N2 C18 117.0(3) . . ?
O0AA C12 S2 122.13(19) . . ?
N2 C12 S2 128.3(2) . . ?
N2 C12 O0AA 109.6(2) . . ?
C9 C13 S1 109.53(18) . . ?
C9 C13 C14 121.5(3) . . ?
C14 C13 S1 129.0(2) . . ?
C21 C14 C13 117.4(3) . . ?
C17 C15 C21 120.9(3) . . ?
C15 C17 C9 118.9(3) . . ?
O3 C19 C8 123.5(4) . . ?
C14 C21 C15 121.6(3) . . ?

_platon_squeeze_details          ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.500 1.000 0.000 115 24 ' '
2 0.301 0.811 0.183 8 0 ' '
3 0.700 0.316 0.324 10 0 ' '
4 0.498 0.501 0.501 114 24 ' '
5 0.301 0.688 0.683 9 0 ' '
6 0.699 0.188 0.816 9 0 ' '

_platon_squeeze_void_probe_radius 1.20
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_xb0887_0m
_database_code_depnum_ccdc_archive 'CCDC 1586906'
_audit_update_record             
;
2018-08-24 deposited with the CCDC.	2019-03-04 downloaded from the CCDC.
;
_audit_creation_date             2017-11-21
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C19 H14 N2 O4 S'
_chemical_formula_sum            'C19 H14 N2 O4 S'
_chemical_formula_weight         366.38
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.806(2)
_cell_length_b                   12.459(4)
_cell_length_c                   17.312(5)
_cell_angle_alpha                85.886(6)
_cell_angle_beta                 89.534(6)
_cell_angle_gamma                76.326(5)
_cell_volume                     1631.7(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    916
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      20.22
_cell_measurement_theta_min      2.36
_shelx_estimated_absorpt_T_max   0.970
_shelx_estimated_absorpt_T_min   0.933
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6629
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0520 before and 0.0428 after correction.
The Ratio of minimum to maximum transmission is 0.8893.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.309
_exptl_crystal_size_mid          0.245
_exptl_crystal_size_min          0.133
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0961
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9138
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.481
_diffrn_reflns_theta_min         1.686
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3405
_reflns_number_total             6526
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.292
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     473
_refine_ls_number_reflns         6526
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1295
_refine_ls_R_factor_gt           0.0642
_refine_ls_restrained_S_all      0.961
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0558P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1271
_refine_ls_wR_factor_ref         0.1592
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C11(H11), C13(H13), C14(H14), C16(H16),
 C21(H21), C22(H22), C23(H23), C24(H24), C30(H30), C32(H32), C33(H33), C35(H35)
2.b Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C37(H37A,H37B,H37C), C38(H38A,H38B,
 H38C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.65200(14) 0.33989(8) 1.11876(6) 0.0555(3) Uani 1 1 d . . . . .
S2 S 0.41582(13) 0.82073(8) 0.45129(6) 0.0556(3) Uani 1 1 d . . . . .
N1 N 0.6427(4) 0.5465(2) 1.08180(16) 0.0470(8) Uani 1 1 d . . . . .
N2 N 1.1843(4) 0.3891(2) 0.53536(18) 0.0542(8) Uani 1 1 d . . . . .
N3 N 0.2823(4) 1.0313(2) 0.45469(16) 0.0434(7) Uani 1 1 d . . . . .
N4 N -0.2857(4) 0.9066(2) 0.99815(17) 0.0491(8) Uani 1 1 d . . . . .
O1 O 0.8361(4) 0.2346(2) 0.99750(17) 0.0840(10) Uani 1 1 d . . . . .
O2 O 0.9333(3) 0.30411(19) 0.89033(14) 0.0523(7) Uani 1 1 d . . . . .
O3 O 1.1561(3) 0.4406(2) 0.65575(15) 0.0594(7) Uani 1 1 d . . . . .
O4 O 0.9839(4) 0.3327(2) 0.61347(15) 0.0675(8) Uani 1 1 d . . . . .
O5 O 0.2979(4) 0.7324(2) 0.58453(16) 0.0759(9) Uani 1 1 d . . . . .
O6 O 0.1439(3) 0.81472(19) 0.67903(14) 0.0521(7) Uani 1 1 d . . . . .
O7 O -0.1716(3) 0.97872(19) 0.89536(13) 0.0527(7) Uani 1 1 d . . . . .
O8 O -0.2625(4) 0.8199(2) 0.88689(15) 0.0624(8) Uani 1 1 d . . . . .
C1 C 0.5630(4) 0.5413(3) 1.1532(2) 0.0434(9) Uani 1 1 d . . . . .
C2 C 0.4914(5) 0.6321(3) 1.1954(2) 0.0534(10) Uani 1 1 d . . . . .
H2 H 0.494342 0.703218 1.176005 0.064 Uiso 1 1 calc R . . . .
C3 C 0.4164(5) 0.6156(4) 1.2657(2) 0.0610(11) Uani 1 1 d . . . . .
H3 H 0.367486 0.676032 1.293932 0.073 Uiso 1 1 calc R . . . .
C4 C 0.4125(5) 0.5106(4) 1.2952(2) 0.0664(12) Uani 1 1 d . . . . .
H4 H 0.360675 0.501168 1.342950 0.080 Uiso 1 1 calc R . . . .
C5 C 0.4843(5) 0.4191(4) 1.2550(2) 0.0619(11) Uani 1 1 d . . . . .
H5 H 0.483654 0.348170 1.275526 0.074 Uiso 1 1 calc R . . . .
C6 C 0.5573(5) 0.4356(3) 1.1833(2) 0.0471(9) Uani 1 1 d . . . . .
C7 C 0.6962(4) 0.4475(3) 1.0576(2) 0.0414(8) Uani 1 1 d . . . . .
C8 C 0.7867(4) 0.4296(3) 0.9835(2) 0.0415(9) Uani 1 1 d . . . . .
C9 C 0.8497(5) 0.3174(3) 0.9605(2) 0.0522(10) Uani 1 1 d . . . . .
C10 C 0.9593(4) 0.3929(3) 0.8432(2) 0.0436(9) Uani 1 1 d . . . . .
C11 C 1.0425(4) 0.3681(3) 0.7736(2) 0.0470(9) Uani 1 1 d . . . . .
H11 H 1.079560 0.295447 0.760057 0.056 Uiso 1 1 calc R . . . .
C12 C 1.0679(5) 0.4547(3) 0.7258(2) 0.0485(9) Uani 1 1 d . . . . .
C13 C 1.0168(5) 0.5636(3) 0.7454(2) 0.0521(10) Uani 1 1 d . . . . .
H13 H 1.039230 0.620698 0.712269 0.063 Uiso 1 1 calc R . . . .
C14 C 0.9329(5) 0.5859(3) 0.8142(2) 0.0527(10) Uani 1 1 d . . . . .
H14 H 0.896126 0.658798 0.827410 0.063 Uiso 1 1 calc R . . . .
C15 C 0.9019(4) 0.4997(3) 0.8649(2) 0.0419(9) Uani 1 1 d . . . . .
C16 C 0.8137(4) 0.5155(3) 0.9367(2) 0.0418(9) Uani 1 1 d . . . . .
H16 H 0.773322 0.587108 0.951987 0.050 Uiso 1 1 calc R . . . .
C17 C 1.0977(5) 0.3814(3) 0.6012(2) 0.0507(10) Uani 1 1 d . . . . .
C18 C 1.3121(5) 0.4568(3) 0.5214(2) 0.0674(12) Uani 1 1 d . . . . .
H18A H 1.349299 0.476860 0.569918 0.101 Uiso 1 1 calc GR . . . .
H18B H 1.258645 0.522594 0.489875 0.101 Uiso 1 1 calc GR . . . .
H18C H 1.412361 0.415435 0.495139 0.101 Uiso 1 1 calc GR . . . .
C19 C 1.1393(6) 0.3323(3) 0.4705(2) 0.0715(12) Uani 1 1 d . . . . .
H19A H 1.230398 0.266734 0.464091 0.107 Uiso 1 1 calc GR . . . .
H19B H 1.128410 0.380506 0.424076 0.107 Uiso 1 1 calc GR . . . .
H19C H 1.029462 0.312114 0.480540 0.107 Uiso 1 1 calc GR . . . .
C20 C 0.4645(5) 0.9075(3) 0.3763(2) 0.0488(9) Uani 1 1 d . . . . .
C21 C 0.5691(5) 0.8778(4) 0.3115(2) 0.0587(11) Uani 1 1 d . . . . .
H21 H 0.625587 0.804608 0.304791 0.070 Uiso 1 1 calc R . . . .
C22 C 0.5839(5) 0.9628(4) 0.2585(2) 0.0676(12) Uani 1 1 d . . . . .
H22 H 0.652158 0.946492 0.214655 0.081 Uiso 1 1 calc R . . . .
C23 C 0.5002(5) 1.0714(4) 0.2686(2) 0.0651(12) Uani 1 1 d . . . . .
H23 H 0.512872 1.126787 0.231486 0.078 Uiso 1 1 calc R . . . .
C24 C 0.3985(5) 1.0990(3) 0.3326(2) 0.0557(10) Uani 1 1 d . . . . .
H24 H 0.342781 1.172537 0.338889 0.067 Uiso 1 1 calc R . . . .
C25 C 0.3799(4) 1.0168(3) 0.3873(2) 0.0447(9) Uani 1 1 d . . . . .
C26 C 0.2899(4) 0.9372(3) 0.49267(19) 0.0409(8) Uani 1 1 d . . . . .
C27 C 0.2011(4) 0.9283(3) 0.56707(19) 0.0403(8) Uani 1 1 d . . . . .
C28 C 0.2213(5) 0.8194(3) 0.6076(2) 0.0507(10) Uani 1 1 d . . . . .
C29 C 0.0516(4) 0.9075(3) 0.7128(2) 0.0424(9) Uani 1 1 d . . . . .
C30 C -0.0128(5) 0.8913(3) 0.7861(2) 0.0465(9) Uani 1 1 d . . . . .
H30 H 0.007590 0.820922 0.811417 0.056 Uiso 1 1 calc R . . . .
C31 C -0.1076(5) 0.9821(3) 0.8205(2) 0.0429(9) Uani 1 1 d . . . . .
C32 C -0.1357(4) 1.0875(3) 0.7835(2) 0.0442(9) Uani 1 1 d . . . . .
H32 H -0.199666 1.148320 0.807945 0.053 Uiso 1 1 calc R . . . .
C33 C -0.0689(4) 1.1019(3) 0.7108(2) 0.0459(9) Uani 1 1 d . . . . .
H33 H -0.087711 1.172601 0.686155 0.055 Uiso 1 1 calc R . . . .
C34 C 0.0268(4) 1.0112(3) 0.67387(19) 0.0366(8) Uani 1 1 d . . . . .
C35 C 0.1059(4) 1.0186(3) 0.59973(19) 0.0397(8) Uani 1 1 d . . . . .
H35 H 0.091548 1.087671 0.573052 0.048 Uiso 1 1 calc R . . . .
C36 C -0.2414(5) 0.8921(3) 0.9247(2) 0.0462(9) Uani 1 1 d . . . . .
C37 C -0.2369(5) 0.9866(3) 1.0446(2) 0.0640(12) Uani 1 1 d . . . . .
H37A H -0.143233 0.949647 1.079614 0.096 Uiso 1 1 calc GR . . . .
H37B H -0.337042 1.022084 1.073692 0.096 Uiso 1 1 calc GR . . . .
H37C H -0.198124 1.041110 1.011490 0.096 Uiso 1 1 calc GR . . . .
C38 C -0.3671(5) 0.8249(3) 1.0389(2) 0.0645(12) Uani 1 1 d . . . . .
H38A H -0.426356 0.791589 1.002249 0.097 Uiso 1 1 calc GR . . . .
H38B H -0.450811 0.860619 1.075466 0.097 Uiso 1 1 calc GR . . . .
H38C H -0.277740 0.768669 1.065820 0.097 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C6 1.726(4) . ?
S1 C7 1.745(3) . ?
S2 C20 1.728(4) . ?
S2 C26 1.746(4) . ?
N1 C1 1.384(4) . ?
N1 C7 1.305(4) . ?
N2 C17 1.329(5) . ?
N2 C18 1.459(4) . ?
N2 C19 1.458(4) . ?
N3 C25 1.388(4) . ?
N3 C26 1.291(4) . ?
N4 C36 1.329(4) . ?
N4 C37 1.444(4) . ?
N4 C38 1.461(4) . ?
O1 C9 1.200(4) . ?
O2 C9 1.376(4) . ?
O2 C10 1.380(4) . ?
O3 C12 1.391(4) . ?
O3 C17 1.382(4) . ?
O4 C17 1.198(4) . ?
O5 C28 1.201(4) . ?
O6 C28 1.376(4) . ?
O6 C29 1.376(4) . ?
O7 C31 1.386(4) . ?
O7 C36 1.383(4) . ?
O8 C36 1.192(4) . ?
C1 C2 1.392(5) . ?
C1 C6 1.391(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.370(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(5) . ?
C4 H4 0.9300 . ?
C4 C5 1.380(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.383(5) . ?
C7 C8 1.464(5) . ?
C8 C9 1.452(5) . ?
C8 C16 1.351(4) . ?
C10 C11 1.384(5) . ?
C10 C15 1.378(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.364(5) . ?
C12 C13 1.386(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.369(5) . ?
C14 H14 0.9300 . ?
C14 C15 1.403(4) . ?
C15 C16 1.419(5) . ?
C16 H16 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 C21 1.400(5) . ?
C20 C25 1.391(5) . ?
C21 H21 0.9300 . ?
C21 C22 1.376(5) . ?
C22 H22 0.9300 . ?
C22 C23 1.380(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.374(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.378(5) . ?
C26 C27 1.467(5) . ?
C27 C28 1.456(5) . ?
C27 C35 1.351(4) . ?
C29 C30 1.381(5) . ?
C29 C34 1.385(4) . ?
C30 H30 0.9300 . ?
C30 C31 1.370(5) . ?
C31 C32 1.388(4) . ?
C32 H32 0.9300 . ?
C32 C33 1.375(5) . ?
C33 H33 0.9300 . ?
C33 C34 1.394(4) . ?
C34 C35 1.426(4) . ?
C35 H35 0.9300 . ?
C37 H37A 0.9600 . ?
C37 H37B 0.9600 . ?
C37 H37C 0.9600 . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 S1 C7 89.07(17) . . ?
C20 S2 C26 88.52(17) . . ?
C7 N1 C1 110.2(3) . . ?
C17 N2 C18 124.8(3) . . ?
C17 N2 C19 117.7(3) . . ?
C19 N2 C18 117.3(3) . . ?
C26 N3 C25 110.6(3) . . ?
C36 N4 C37 125.3(3) . . ?
C36 N4 C38 117.5(3) . . ?
C37 N4 C38 116.5(3) . . ?
C9 O2 C10 122.1(3) . . ?
C17 O3 C12 119.1(3) . . ?
C29 O6 C28 122.8(3) . . ?
C36 O7 C31 121.4(3) . . ?
N1 C1 C2 125.0(3) . . ?
N1 C1 C6 115.5(3) . . ?
C6 C1 C2 119.5(3) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.3(4) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.8(4) . . ?
C4 C3 H3 119.6 . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 121.1(4) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 120.8 . . ?
C4 C5 C6 118.3(4) . . ?
C6 C5 H5 120.8 . . ?
C1 C6 S1 109.5(3) . . ?
C5 C6 S1 129.4(3) . . ?
C5 C6 C1 121.1(4) . . ?
N1 C7 S1 115.7(3) . . ?
N1 C7 C8 121.3(3) . . ?
C8 C7 S1 123.0(3) . . ?
C9 C8 C7 119.2(3) . . ?
C16 C8 C7 121.2(3) . . ?
C16 C8 C9 119.5(3) . . ?
O1 C9 O2 116.8(3) . . ?
O1 C9 C8 125.7(4) . . ?
O2 C9 C8 117.5(3) . . ?
O2 C10 C11 116.2(3) . . ?
C15 C10 O2 120.9(3) . . ?
C15 C10 C11 122.9(3) . . ?
C10 C11 H11 121.4 . . ?
C12 C11 C10 117.2(3) . . ?
C12 C11 H11 121.4 . . ?
C11 C12 O3 122.8(3) . . ?
C11 C12 C13 122.4(3) . . ?
C13 C12 O3 114.7(3) . . ?
C12 C13 H13 120.4 . . ?
C14 C13 C12 119.1(3) . . ?
C14 C13 H13 120.4 . . ?
C13 C14 H14 119.7 . . ?
C13 C14 C15 120.5(3) . . ?
C15 C14 H14 119.7 . . ?
C10 C15 C14 117.8(3) . . ?
C10 C15 C16 118.0(3) . . ?
C14 C15 C16 124.2(3) . . ?
C8 C16 C15 122.0(3) . . ?
C8 C16 H16 119.0 . . ?
C15 C16 H16 119.0 . . ?
N2 C17 O3 109.8(3) . . ?
O4 C17 N2 127.0(4) . . ?
O4 C17 O3 123.2(3) . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N2 C19 H19A 109.5 . . ?
N2 C19 H19B 109.5 . . ?
N2 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 S2 127.6(3) . . ?
C25 C20 S2 110.0(3) . . ?
C25 C20 C21 122.4(4) . . ?
C20 C21 H21 121.8 . . ?
C22 C21 C20 116.5(4) . . ?
C22 C21 H21 121.8 . . ?
C21 C22 H22 119.1 . . ?
C21 C22 C23 121.8(4) . . ?
C23 C22 H22 119.1 . . ?
C22 C23 H23 119.5 . . ?
C24 C23 C22 121.0(4) . . ?
C24 C23 H23 119.5 . . ?
C23 C24 H24 120.3 . . ?
C23 C24 C25 119.3(4) . . ?
C25 C24 H24 120.3 . . ?
N3 C25 C20 114.8(3) . . ?
C24 C25 N3 126.1(4) . . ?
C24 C25 C20 119.1(3) . . ?
N3 C26 S2 116.1(3) . . ?
N3 C26 C27 122.2(3) . . ?
C27 C26 S2 121.7(3) . . ?
C28 C27 C26 118.8(3) . . ?
C35 C27 C26 121.7(3) . . ?
C35 C27 C28 119.5(3) . . ?
O5 C28 O6 116.2(3) . . ?
O5 C28 C27 126.5(4) . . ?
O6 C28 C27 117.2(3) . . ?
O6 C29 C30 116.7(3) . . ?
O6 C29 C34 120.5(3) . . ?
C30 C29 C34 122.8(3) . . ?
C29 C30 H30 121.1 . . ?
C31 C30 C29 117.9(3) . . ?
C31 C30 H30 121.1 . . ?
O7 C31 C32 114.7(3) . . ?
C30 C31 O7 123.9(3) . . ?
C30 C31 C32 121.3(3) . . ?
C31 C32 H32 120.0 . . ?
C33 C32 C31 119.9(3) . . ?
C33 C32 H32 120.0 . . ?
C32 C33 H33 119.8 . . ?
C32 C33 C34 120.3(3) . . ?
C34 C33 H33 119.8 . . ?
C29 C34 C33 117.9(3) . . ?
C29 C34 C35 117.9(3) . . ?
C33 C34 C35 124.2(3) . . ?
C27 C35 C34 122.0(3) . . ?
C27 C35 H35 119.0 . . ?
C34 C35 H35 119.0 . . ?
N4 C36 O7 109.2(3) . . ?
O8 C36 N4 127.4(3) . . ?
O8 C36 O7 123.4(3) . . ?
N4 C37 H37A 109.5 . . ?
N4 C37 H37B 109.5 . . ?
N4 C37 H37C 109.5 . . ?
H37A C37 H37B 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
N4 C38 H38A 109.5 . . ?
N4 C38 H38B 109.5 . . ?
N4 C38 H38C 109.5 . . ?
H38A C38 H38B 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
S1 C7 C8 C9 -2.6(5) . . . . ?
S1 C7 C8 C16 178.0(3) . . . . ?
S2 C20 C21 C22 178.3(3) . . . . ?
S2 C20 C25 N3 1.4(4) . . . . ?
S2 C20 C25 C24 -178.5(3) . . . . ?
S2 C26 C27 C28 0.9(4) . . . . ?
S2 C26 C27 C35 178.9(3) . . . . ?
N1 C1 C2 C3 -179.9(3) . . . . ?
N1 C1 C6 S1 -1.0(4) . . . . ?
N1 C1 C6 C5 178.7(3) . . . . ?
N1 C7 C8 C9 177.6(3) . . . . ?
N1 C7 C8 C16 -1.8(5) . . . . ?
N3 C26 C27 C28 -177.8(3) . . . . ?
N3 C26 C27 C35 0.2(5) . . . . ?
O2 C10 C11 C12 179.3(3) . . . . ?
O2 C10 C15 C14 180.0(3) . . . . ?
O2 C10 C15 C16 -0.7(5) . . . . ?
O3 C12 C13 C14 -178.4(3) . . . . ?
O6 C29 C30 C31 -179.0(3) . . . . ?
O6 C29 C34 C33 179.5(3) . . . . ?
O6 C29 C34 C35 -2.5(5) . . . . ?
O7 C31 C32 C33 176.2(3) . . . . ?
C1 N1 C7 S1 0.8(4) . . . . ?
C1 N1 C7 C8 -179.4(3) . . . . ?
C1 C2 C3 C4 0.5(6) . . . . ?
C2 C1 C6 S1 179.1(3) . . . . ?
C2 C1 C6 C5 -1.1(5) . . . . ?
C2 C3 C4 C5 0.2(6) . . . . ?
C3 C4 C5 C6 -1.3(6) . . . . ?
C4 C5 C6 S1 -178.5(3) . . . . ?
C4 C5 C6 C1 1.8(6) . . . . ?
C6 S1 C7 N1 -1.2(3) . . . . ?
C6 S1 C7 C8 179.0(3) . . . . ?
C6 C1 C2 C3 0.0(5) . . . . ?
C7 S1 C6 C1 1.2(3) . . . . ?
C7 S1 C6 C5 -178.5(4) . . . . ?
C7 N1 C1 C2 180.0(3) . . . . ?
C7 N1 C1 C6 0.2(4) . . . . ?
C7 C8 C9 O1 -0.6(6) . . . . ?
C7 C8 C9 O2 179.7(3) . . . . ?
C7 C8 C16 C15 179.7(3) . . . . ?
C9 O2 C10 C11 -179.0(3) . . . . ?
C9 O2 C10 C15 0.0(5) . . . . ?
C9 C8 C16 C15 0.3(5) . . . . ?
C10 O2 C9 O1 -178.9(3) . . . . ?
C10 O2 C9 C8 0.8(5) . . . . ?
C10 C11 C12 O3 177.3(3) . . . . ?
C10 C11 C12 C13 1.3(5) . . . . ?
C10 C15 C16 C8 0.5(5) . . . . ?
C11 C10 C15 C14 -1.1(5) . . . . ?
C11 C10 C15 C16 178.2(3) . . . . ?
C11 C12 C13 C14 -2.1(6) . . . . ?
C12 O3 C17 N2 172.2(3) . . . . ?
C12 O3 C17 O4 -6.9(5) . . . . ?
C12 C13 C14 C15 1.2(6) . . . . ?
C13 C14 C15 C10 0.3(5) . . . . ?
C13 C14 C15 C16 -179.0(3) . . . . ?
C14 C15 C16 C8 179.8(3) . . . . ?
C15 C10 C11 C12 0.4(5) . . . . ?
C16 C8 C9 O1 178.8(4) . . . . ?
C16 C8 C9 O2 -0.9(5) . . . . ?
C17 O3 C12 C11 55.7(5) . . . . ?
C17 O3 C12 C13 -128.0(3) . . . . ?
C18 N2 C17 O3 -4.3(5) . . . . ?
C18 N2 C17 O4 174.8(4) . . . . ?
C19 N2 C17 O3 -179.5(3) . . . . ?
C19 N2 C17 O4 -0.5(6) . . . . ?
C20 S2 C26 N3 0.6(3) . . . . ?
C20 S2 C26 C27 -178.1(3) . . . . ?
C20 C21 C22 C23 0.1(6) . . . . ?
C21 C20 C25 N3 -179.8(3) . . . . ?
C21 C20 C25 C24 0.4(5) . . . . ?
C21 C22 C23 C24 0.1(6) . . . . ?
C22 C23 C24 C25 -0.1(6) . . . . ?
C23 C24 C25 N3 180.0(3) . . . . ?
C23 C24 C25 C20 -0.1(5) . . . . ?
C25 N3 C26 S2 0.1(4) . . . . ?
C25 N3 C26 C27 178.8(3) . . . . ?
C25 C20 C21 C22 -0.3(5) . . . . ?
C26 S2 C20 C21 -179.8(3) . . . . ?
C26 S2 C20 C25 -1.1(3) . . . . ?
C26 N3 C25 C20 -1.0(4) . . . . ?
C26 N3 C25 C24 178.9(3) . . . . ?
C26 C27 C28 O5 -4.0(6) . . . . ?
C26 C27 C28 O6 176.7(3) . . . . ?
C26 C27 C35 C34 -176.7(3) . . . . ?
C28 O6 C29 C30 -177.3(3) . . . . ?
C28 O6 C29 C34 2.5(5) . . . . ?
C28 C27 C35 C34 1.3(5) . . . . ?
C29 O6 C28 O5 -179.9(3) . . . . ?
C29 O6 C28 C27 -0.6(5) . . . . ?
C29 C30 C31 O7 -176.4(3) . . . . ?
C29 C30 C31 C32 -1.1(5) . . . . ?
C29 C34 C35 C27 0.6(5) . . . . ?
C30 C29 C34 C33 -0.7(5) . . . . ?
C30 C29 C34 C35 177.3(3) . . . . ?
C30 C31 C32 C33 0.5(5) . . . . ?
C31 O7 C36 N4 177.4(3) . . . . ?
C31 O7 C36 O8 -5.3(5) . . . . ?
C31 C32 C33 C34 0.1(5) . . . . ?
C32 C33 C34 C29 0.0(5) . . . . ?
C32 C33 C34 C35 -177.8(3) . . . . ?
C33 C34 C35 C27 178.4(3) . . . . ?
C34 C29 C30 C31 1.2(5) . . . . ?
C35 C27 C28 O5 177.9(4) . . . . ?
C35 C27 C28 O6 -1.4(5) . . . . ?
C36 O7 C31 C30 -39.6(5) . . . . ?
C36 O7 C31 C32 144.8(3) . . . . ?
C37 N4 C36 O7 -11.5(5) . . . . ?
C37 N4 C36 O8 171.3(4) . . . . ?
C38 N4 C36 O7 178.3(3) . . . . ?
C38 N4 C36 O8 1.1(6) . . . . ?

_shelx_SHELXL_version_number     2016/6
_olex2_submission_special_instructions 'No special instructions were received'
