# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_zhh
_database_code_depnum_ccdc_archive 'CCDC 1952781'
loop_
_audit_author_name
_audit_author_address
'IMfirst IMsecond'
;Anhui University
China
;
_audit_update_record             
;
2019-09-11 deposited with the CCDC.	2020-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H23 I N2'
_chemical_formula_weight         454.33

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/c  '

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

_cell_length_a                   9.759(6)
_cell_length_b                   14.912(10)
_cell_length_c                   14.143(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.115(6)
_cell_angle_gamma                90.00
_cell_volume                     1996(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9714
_cell_measurement_theta_min      2.15
_cell_measurement_theta_max      27.27

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             912
_exptl_absorpt_coefficient_mu    1.613
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13698
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_av_sigmaI/netI    0.0187
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3513
_reflns_number_gt                3154
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0499P)²+0.8827P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3513
_refine_ls_number_parameters     240
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0862
_refine_ls_wR_factor_gt          0.0837
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.79010(2) 0.747217(11) 0.605524(13) 0.05481(11) Uani 1 1 d . . .
C1 C 0.1975(2) 0.53714(15) 0.11092(15) 0.0367(5) Uani 1 1 d . . .
N2 N 0.1886(2) 0.64386(14) 0.23801(14) 0.0460(5) Uani 1 1 d . . .
C2 C 0.4339(2) 0.62339(16) -0.04387(17) 0.0436(5) Uani 1 1 d . . .
H2 H 0.4730 0.6728 -0.0069 0.052 Uiso 1 1 calc R . .
C3 C 0.4386(2) 0.54069(16) -0.20733(16) 0.0409(5) Uani 1 1 d . . .
C4 C 0.1519(2) 0.45311(15) 0.06663(16) 0.0418(5) Uani 1 1 d . . .
H4 H 0.1878 0.4331 0.0152 0.050 Uiso 1 1 calc R . .
C5 C 0.1410(2) 0.56455(16) 0.19004(15) 0.0409(5) Uani 1 1 d . . .
C6 C 0.3430(2) 0.57324(16) -0.00798(16) 0.0417(5) Uani 1 1 d . . .
H6 H 0.3070 0.5217 -0.0421 0.050 Uiso 1 1 calc R . .
C7 C 0.2978(2) 0.59359(15) 0.07920(16) 0.0393(5) Uani 1 1 d . . .
C8 C 0.0565(3) 0.40133(18) 0.09824(19) 0.0535(6) Uani 1 1 d . . .
H8 H 0.0302 0.3458 0.0697 0.064 Uiso 1 1 calc R . .
C9 C 0.5151(2) 0.56100(18) -0.27750(17) 0.0475(6) Uani 1 1 d . . .
C10 C 0.5719(3) 0.66522(18) -0.16189(18) 0.0501(6) Uani 1 1 d . . .
H10 H 0.6150 0.7149 -0.1272 0.060 Uiso 1 1 calc R . .
C11 C 0.4769(2) 0.60907(16) -0.13245(16) 0.0417(5) Uani 1 1 d . . .
C12 C 0.3453(3) 0.66929(18) 0.13595(18) 0.0523(6) Uani 1 1 d . . .
H12 H 0.4157 0.7049 0.1213 0.063 Uiso 1 1 calc R . .
N1 N 0.5929(2) 0.63784(17) -0.24731(16) 0.0541(6) Uani 1 1 d . . .
C13 C -0.0017(3) 0.4317(2) 0.1733(2) 0.0594(7) Uani 1 1 d . . .
H13 H -0.0689 0.3969 0.1929 0.071 Uiso 1 1 calc R . .
C14 C 0.5069(3) 0.5091(2) -0.36041(18) 0.0585(7) Uani 1 1 d . . .
H14 H 0.5586 0.5237 -0.4055 0.070 Uiso 1 1 calc R . .
C15 C 0.2899(3) 0.69167(18) 0.21255(18) 0.0540(6) Uani 1 1 d . . .
H15 H 0.3241 0.7425 0.2487 0.065 Uiso 1 1 calc R . .
C16 C 0.0384(3) 0.5115(2) 0.21804(18) 0.0543(6) Uani 1 1 d . . .
H16 H -0.0021 0.5311 0.2674 0.065 Uiso 1 1 calc R . .
C17 C 0.3522(3) 0.46419(17) -0.22208(17) 0.0463(5) Uani 1 1 d . . .
H17 H 0.3016 0.4484 -0.1768 0.056 Uiso 1 1 calc R . .
C18 C 0.3431(3) 0.41267(19) -0.3045(2) 0.0574(6) Uani 1 1 d . . .
H18 H 0.2854 0.3622 -0.3145 0.069 Uiso 1 1 calc R . .
C19 C 0.4191(3) 0.4350(2) -0.3733(2) 0.0632(7) Uani 1 1 d . . .
H19 H 0.4104 0.3994 -0.4285 0.076 Uiso 1 1 calc R . .
C20 C 0.1301(3) 0.67681(19) 0.31926(18) 0.0561(7) Uani 1 1 d . . .
H20A H 0.0281 0.6712 0.3004 0.067 Uiso 1 1 calc R . .
H20B H 0.1524 0.7400 0.3295 0.067 Uiso 1 1 calc R . .
C21 C 0.1854(3) 0.6275(2) 0.41431(18) 0.0608(7) Uani 1 1 d . . .
H21A H 0.2843 0.6420 0.4406 0.073 Uiso 1 1 calc R . .
H21B H 0.1776 0.5633 0.4032 0.073 Uiso 1 1 calc R . .
C22 C 0.1002(4) 0.6548(2) 0.4866(2) 0.0746(9) Uani 1 1 d . . .
H22A H 0.1155 0.7181 0.5013 0.090 Uiso 1 1 calc R . .
H22B H 0.0005 0.6466 0.4563 0.090 Uiso 1 1 calc R . .
C23 C 0.1367(5) 0.6030(3) 0.5798(3) 0.1019(14) Uani 1 1 d . . .
H23A H 0.1247 0.5401 0.5659 0.153 Uiso 1 1 calc R . .
H23B H 0.0757 0.6210 0.6204 0.153 Uiso 1 1 calc R . .
H23C H 0.2332 0.6147 0.6131 0.153 Uiso 1 1 calc R . .
H100 H 0.643(3) 0.657(2) -0.270(2) 0.060(9) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C4 1.423(3) . ?
C1 C5 1.423(3) . ?
C1 C7 1.443(3) . ?
N2 C15 1.337(3) . ?
N2 C5 1.386(3) . ?
N2 C20 1.486(3) . ?
C2 C6 1.350(3) . ?
C2 C11 1.431(3) . ?
C2 H2 0.9300 . ?
C3 C17 1.404(3) . ?
C3 C9 1.413(3) . ?
C3 C11 1.452(3) . ?
C4 C8 1.367(3) . ?
C4 H4 0.9300 . ?
C5 C16 1.406(4) . ?
C6 C7 1.440(3) . ?
C6 H6 0.9300 . ?
C7 C12 1.397(3) . ?
C8 C13 1.396(4) . ?
C8 H8 0.9300 . ?
C9 N1 1.383(4) . ?
C9 C14 1.391(4) . ?
C10 N1 1.337(4) . ?
C10 C11 1.387(3) . ?
C10 H10 0.9300 . ?
C12 C15 1.365(4) . ?
C12 H12 0.9300 . ?
N1 H100 0.71(3) . ?
C13 C16 1.359(4) . ?
C13 H13 0.9300 . ?
C14 C19 1.383(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C18 1.381(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.399(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 C21 1.511(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.522(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 C23 1.494(4) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
C4 C1 C5 117.4(2) . . ?
C4 C1 C7 122.7(2) . . ?
C5 C1 C7 120.0(2) . . ?
C15 N2 C5 120.32(19) . . ?
C15 N2 C20 118.7(2) . . ?
C5 N2 C20 121.0(2) . . ?
C6 C2 C11 127.3(2) . . ?
C6 C2 H2 116.3 . . ?
C11 C2 H2 116.3 . . ?
C17 C3 C9 118.1(2) . . ?
C17 C3 C11 135.9(2) . . ?
C9 C3 C11 106.0(2) . . ?
C8 C4 C1 121.2(2) . . ?
C8 C4 H4 119.4 . . ?
C1 C4 H4 119.4 . . ?
N2 C5 C16 121.3(2) . . ?
N2 C5 C1 118.8(2) . . ?
C16 C5 C1 119.9(2) . . ?
C2 C6 C7 124.9(2) . . ?
C2 C6 H6 117.6 . . ?
C7 C6 H6 117.6 . . ?
C12 C7 C6 122.3(2) . . ?
C12 C7 C1 116.6(2) . . ?
C6 C7 C1 121.1(2) . . ?
C4 C8 C13 120.1(2) . . ?
C4 C8 H8 120.0 . . ?
C13 C8 H8 120.0 . . ?
N1 C9 C14 129.5(2) . . ?
N1 C9 C3 107.8(2) . . ?
C14 C9 C3 122.8(2) . . ?
N1 C10 C11 110.3(2) . . ?
N1 C10 H10 124.8 . . ?
C11 C10 H10 124.8 . . ?
C10 C11 C2 122.2(2) . . ?
C10 C11 C3 106.1(2) . . ?
C2 C11 C3 131.7(2) . . ?
C15 C12 C7 120.9(2) . . ?
C15 C12 H12 119.6 . . ?
C7 C12 H12 119.6 . . ?
C10 N1 C9 109.8(2) . . ?
C10 N1 H100 124(3) . . ?
C9 N1 H100 126(3) . . ?
C16 C13 C8 120.9(2) . . ?
C16 C13 H13 119.5 . . ?
C8 C13 H13 119.5 . . ?
C19 C14 C9 117.5(2) . . ?
C19 C14 H14 121.2 . . ?
C9 C14 H14 121.2 . . ?
N2 C15 C12 123.0(2) . . ?
N2 C15 H15 118.5 . . ?
C12 C15 H15 118.5 . . ?
C13 C16 C5 120.3(2) . . ?
C13 C16 H16 119.8 . . ?
C5 C16 H16 119.8 . . ?
C18 C17 C3 119.4(2) . . ?
C18 C17 H17 120.3 . . ?
C3 C17 H17 120.3 . . ?
C17 C18 C19 121.3(3) . . ?
C17 C18 H18 119.4 . . ?
C19 C18 H18 119.4 . . ?
C14 C19 C18 120.9(3) . . ?
C14 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
N2 C20 C21 114.0(2) . . ?
N2 C20 H20A 108.8 . . ?
C21 C20 H20A 108.8 . . ?
N2 C20 H20B 108.8 . . ?
C21 C20 H20B 108.8 . . ?
H20A C20 H20B 107.7 . . ?
C20 C21 C22 109.4(2) . . ?
C20 C21 H21A 109.8 . . ?
C22 C21 H21A 109.8 . . ?
C20 C21 H21B 109.8 . . ?
C22 C21 H21B 109.8 . . ?
H21A C21 H21B 108.2 . . ?
C23 C22 C21 113.7(3) . . ?
C23 C22 H22A 108.8 . . ?
C21 C22 H22A 108.8 . . ?
C23 C22 H22B 108.8 . . ?
C21 C22 H22B 108.8 . . ?
H22A C22 H22B 107.7 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
C5 C1 C4 C8 0.7(3) . . . . ?
C7 C1 C4 C8 -179.8(2) . . . . ?
C15 N2 C5 C16 177.6(2) . . . . ?
C20 N2 C5 C16 -1.6(3) . . . . ?
C15 N2 C5 C1 -2.6(3) . . . . ?
C20 N2 C5 C1 178.3(2) . . . . ?
C4 C1 C5 N2 176.8(2) . . . . ?
C7 C1 C5 N2 -2.8(3) . . . . ?
C4 C1 C5 C16 -3.4(3) . . . . ?
C7 C1 C5 C16 177.1(2) . . . . ?
C11 C2 C6 C7 -176.5(2) . . . . ?
C2 C6 C7 C12 0.0(4) . . . . ?
C2 C6 C7 C1 178.5(2) . . . . ?
C4 C1 C7 C12 -173.0(2) . . . . ?
C5 C1 C7 C12 6.5(3) . . . . ?
C4 C1 C7 C6 8.4(3) . . . . ?
C5 C1 C7 C6 -172.1(2) . . . . ?
C1 C4 C8 C13 2.0(4) . . . . ?
C17 C3 C9 N1 -179.4(2) . . . . ?
C11 C3 C9 N1 -0.9(2) . . . . ?
C17 C3 C9 C14 0.7(3) . . . . ?
C11 C3 C9 C14 179.2(2) . . . . ?
N1 C10 C11 C2 -179.3(2) . . . . ?
N1 C10 C11 C3 0.7(3) . . . . ?
C6 C2 C11 C10 -179.7(2) . . . . ?
C6 C2 C11 C3 0.2(4) . . . . ?
C17 C3 C11 C10 178.2(3) . . . . ?
C9 C3 C11 C10 0.1(2) . . . . ?
C17 C3 C11 C2 -1.8(4) . . . . ?
C9 C3 C11 C2 -179.9(2) . . . . ?
C6 C7 C12 C15 173.4(2) . . . . ?
C1 C7 C12 C15 -5.2(4) . . . . ?
C11 C10 N1 C9 -1.4(3) . . . . ?
C14 C9 N1 C10 -178.7(3) . . . . ?
C3 C9 N1 C10 1.4(3) . . . . ?
C4 C8 C13 C16 -2.1(4) . . . . ?
N1 C9 C14 C19 -179.6(3) . . . . ?
C3 C9 C14 C19 0.2(4) . . . . ?
C5 N2 C15 C12 4.1(4) . . . . ?
C20 N2 C15 C12 -176.7(3) . . . . ?
C7 C12 C15 N2 0.0(4) . . . . ?
C8 C13 C16 C5 -0.7(4) . . . . ?
N2 C5 C16 C13 -176.7(2) . . . . ?
C1 C5 C16 C13 3.5(4) . . . . ?
C9 C3 C17 C18 -1.0(3) . . . . ?
C11 C3 C17 C18 -179.0(3) . . . . ?
C3 C17 C18 C19 0.4(4) . . . . ?
C9 C14 C19 C18 -0.9(4) . . . . ?
C17 C18 C19 C14 0.6(4) . . . . ?
C15 N2 C20 C21 -102.7(3) . . . . ?
C5 N2 C20 C21 76.4(3) . . . . ?
N2 C20 C21 C22 -170.0(3) . . . . ?
C20 C21 C22 C23 174.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.336
_refine_diff_density_min         -1.279
_refine_diff_density_rms         0.104
####################################################################### 
# 
# 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_ss
_database_code_depnum_ccdc_archive 'CCDC 1952782'
loop_
_audit_author_name
_audit_author_address
'IMfirst IMsecond'
;Anhui University
China
;
_audit_update_record             
;
2019-09-11 deposited with the CCDC.	2020-01-06 downloaded from the CCDC.
;
_audit_creation_date             2019-09-10
_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         'C22 H20 N2 O3 S, C H4 O'
_chemical_formula_sum            'C23 H24 N2 O4 S'
_chemical_formula_weight         424.50
_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                   10.532(2)
_cell_length_b                   13.748(3)
_cell_length_c                   14.154(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.091(2)
_cell_angle_gamma                90
_cell_volume                     2048.0(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6289
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.00
_cell_measurement_theta_min      2.44
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.4128
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1039 before and 0.0318 after correction.
The Ratio of minimum to maximum transmission is 0.5537.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.377
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             896
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0826
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            15714
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.340
_diffrn_reflns_theta_min         1.935
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_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                3541
_reflns_number_total             4282
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.237
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         4282
_refine_ls_number_restraints     270
_refine_ls_R_factor_all          0.0526
_refine_ls_R_factor_gt           0.0422
_refine_ls_restrained_S_all      1.017
_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)+(0.0501P)²+0.5457P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1087
_refine_ls_wR_factor_ref         0.1162
_refine_special_details          ?
_olex2_refinement_description    
;
1. Uiso/Uaniso restraints and constraints
C3AA \\sim C2AA \\sim C \\sim C4AA \\sim C5AA \\sim C0AA \\sim C6AA \\sim C0CA
\\sim C1AA \\sim C9AA \\sim C7AA \\sim C0BA \\sim C1BA \\sim C2BA \\sim C3BA
\\sim C4BA \\sim C5BA \\sim C6BA \\sim C7BA \\sim C8AA \\sim C8BA \\sim C9BA
\\sim C2: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C3AA) \\sim Ueq, Uanis(C2AA) \\sim Ueq, Uanis(C) \\sim Ueq, Uanis(C4AA)
\\sim Ueq, Uanis(C5AA) \\sim Ueq, Uanis(C0AA) \\sim Ueq, Uanis(C6AA) \\sim Ueq,
Uanis(C0CA) \\sim Ueq, Uanis(C1AA) \\sim Ueq, Uanis(C9AA) \\sim Ueq,
Uanis(C7AA) \\sim Ueq, Uanis(C0BA) \\sim Ueq, Uanis(C1BA) \\sim Ueq,
Uanis(C2BA) \\sim Ueq, Uanis(C3BA) \\sim Ueq, Uanis(C4BA) \\sim Ueq,
Uanis(C5BA) \\sim Ueq, Uanis(C6BA) \\sim Ueq, Uanis(C7BA) \\sim Ueq,
Uanis(C8AA) \\sim Ueq, Uanis(C8BA) \\sim Ueq, Uanis(C9BA) \\sim Ueq, Uanis(C2)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_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
S S 0.75671(4) 0.10948(3) 0.10596(3) 0.03292(14) Uani 1 1 d . . . . .
N1AA N 0.13158(14) 0.12243(11) -0.56350(10) 0.0380(3) Uani 1 1 d . . . . .
O0AA O 0.87629(12) 0.15162(10) 0.07904(9) 0.0458(3) Uani 1 1 d . . . . .
O1AA O 0.76952(11) 0.05621(9) 0.19518(8) 0.0399(3) Uani 1 1 d . . . . .
C3AA C 0.79795(18) -0.11967(13) -0.08162(12) 0.0354(4) Uani 1 1 d . U . . .
C2AA C 0.22209(15) 0.18431(12) -0.59786(11) 0.0338(4) Uani 1 1 d . U . . .
N3AA N 0.73141(12) -0.07589(9) -0.16553(9) 0.0297(3) Uani 1 1 d . . . . .
C C 0.71588(17) 0.01998(14) 0.01865(13) 0.0379(4) Uani 1 1 d . U . . .
O5AA O 0.65085(12) 0.17698(9) 0.10379(10) 0.0475(3) Uani 1 1 d . . . . .
C4AA C 0.60691(16) -0.09224(13) -0.17925(12) 0.0354(4) Uani 1 1 d . U . . .
C5AA C 0.72113(14) 0.04182(11) -0.29319(10) 0.0283(3) Uani 1 1 d . U . . .
C0AA C 0.31044(15) 0.09652(12) -0.47467(11) 0.0321(4) Uani 1 1 d . U . . .
C6AA C 0.39020(16) 0.05155(13) -0.40328(12) 0.0348(4) Uani 1 1 d . U . . .
C0CA C 0.44164(17) 0.22800(13) -0.56600(14) 0.0419(4) Uani 1 1 d . U . . .
C1AA C 0.79322(14) -0.01099(11) -0.22390(10) 0.0278(3) Uani 1 1 d . U . . .
C9AA C 0.33598(15) 0.17115(12) -0.54370(11) 0.0315(3) Uani 1 1 d . U . . .
C7AA C 0.82734(16) -0.04453(14) -0.00463(12) 0.0364(4) Uani 1 1 d . U . . .
C0BA C 0.92575(15) 0.00091(12) -0.21419(11) 0.0324(4) Uani 1 1 d . U . . .
C1BA C 0.58739(14) 0.02291(12) -0.30775(11) 0.0307(3) Uani 1 1 d . U . . .
C2BA C 0.2105(2) 0.24978(14) -0.67283(14) 0.0450(4) Uani 1 1 d . U . . .
C3BA C 0.78706(17) 0.11123(12) -0.34678(13) 0.0363(4) Uani 1 1 d . U . . .
C4BA C 0.91487(17) 0.12413(13) -0.33515(14) 0.0406(4) Uani 1 1 d . U . . .
C5BA C 0.18422(16) 0.07015(14) -0.49144(12) 0.0376(4) Uani 1 1 d . U . . .
C6BA C 0.53471(16) -0.04636(13) -0.24861(12) 0.0358(4) Uani 1 1 d . U . . .
C7BA C 0.98471(16) 0.06701(13) -0.27016(13) 0.0378(4) Uani 1 1 d . U . . .
C8AA C 0.51246(16) 0.07268(13) -0.37996(12) 0.0352(4) Uani 1 1 d . U . . .
C8BA C 0.4295(2) 0.29269(16) -0.64015(16) 0.0544(5) Uani 1 1 d . U . . .
C9BA C 0.3161(2) 0.30352(16) -0.69300(16) 0.0549(5) Uani 1 1 d . U . . .
O1 O 0.88356(14) 0.13307(12) 0.35657(11) 0.0574(4) Uani 1 1 d . . . . .
C2 C 0.8107(3) 0.2149(3) 0.3775(2) 0.0757(8) Uani 1 1 d . U . . .
H0BA H 0.9769(17) -0.0356(13) -0.1705(12) 0.032(4) Uiso 1 1 d . . . . .
H3AA H 0.8748(18) -0.1511(13) -0.1032(12) 0.035(5) Uiso 1 1 d . . . . .
H4AA H 0.5667(18) -0.1372(14) -0.1359(13) 0.041(5) Uiso 1 1 d . . . . .
H3AB H 0.7387(19) -0.1661(14) -0.0587(13) 0.042(5) Uiso 1 1 d . . . . .
H6BA H 0.449(2) -0.0614(14) -0.2532(13) 0.042(5) Uiso 1 1 d . . . . .
H7BA H 1.0739(19) 0.0729(14) -0.2614(12) 0.040(5) Uiso 1 1 d . . . . .
H7AA H 0.859(2) -0.0816(15) 0.0518(15) 0.055(6) Uiso 1 1 d . . . . .
H5BA H 0.1379(19) 0.0211(15) -0.4591(13) 0.045(5) Uiso 1 1 d . . . . .
H4BA H 0.9564(17) 0.1719(14) -0.3728(12) 0.038(5) Uiso 1 1 d . . . . .
H7AB H 0.897(2) -0.0025(15) -0.0198(14) 0.048(5) Uiso 1 1 d . . . . .
H3BA H 0.739(2) 0.1506(15) -0.3905(14) 0.051(6) Uiso 1 1 d . . . . .
H6AA H 0.3530(19) 0.0025(15) -0.3687(13) 0.046(5) Uiso 1 1 d . . . . .
HA H 0.687(2) 0.0559(16) -0.0368(16) 0.057(6) Uiso 1 1 d . . . . .
H1AA H 0.052(2) 0.1191(16) -0.5902(16) 0.059(6) Uiso 1 1 d . . . . .
H0CA H 0.523(2) 0.2225(15) -0.5290(13) 0.049(5) Uiso 1 1 d . . . . .
H8AA H 0.553(2) 0.1242(15) -0.4133(14) 0.050(6) Uiso 1 1 d . . . . .
HB H 0.644(2) -0.0162(16) 0.0405(14) 0.058(6) Uiso 1 1 d . . . . .
H2BA H 0.131(2) 0.2527(15) -0.7087(14) 0.051(6) Uiso 1 1 d . . . . .
H8BA H 0.499(2) 0.3297(18) -0.6550(16) 0.066(7) Uiso 1 1 d . . . . .
H9BA H 0.311(2) 0.3540(19) -0.7422(18) 0.080(8) Uiso 1 1 d . . . . .
H1 H 0.853(3) 0.112(2) 0.303(2) 0.084(9) Uiso 1 1 d . . . . .
H2A H 0.841(4) 0.238(3) 0.438(3) 0.144(15) Uiso 1 1 d . . . . .
H2B H 0.732(5) 0.187(4) 0.394(3) 0.19(2) Uiso 1 1 d . . . . .
H2C H 0.822(5) 0.258(4) 0.336(4) 0.22(3) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S O0AA 1.4499(13) . ?
S O1AA 1.4618(12) . ?
S C 1.7853(18) . ?
S O5AA 1.4501(13) . ?
N1AA C2AA 1.379(2) . ?
N1AA C5BA 1.350(2) . ?
C3AA N3AA 1.484(2) . ?
C3AA C7AA 1.525(2) . ?
C2AA C9AA 1.411(2) . ?
C2AA C2BA 1.393(2) . ?
N3AA C4AA 1.338(2) . ?
N3AA C1AA 1.3934(19) . ?
C C7AA 1.517(2) . ?
C4AA C6BA 1.373(2) . ?
C5AA C1AA 1.418(2) . ?
C5AA C1BA 1.440(2) . ?
C5AA C3BA 1.416(2) . ?
C0AA C6AA 1.431(2) . ?
C0AA C9AA 1.449(2) . ?
C0AA C5BA 1.390(2) . ?
C6AA C8AA 1.349(2) . ?
C0CA C9AA 1.405(2) . ?
C0CA C8BA 1.378(3) . ?
C1AA C0BA 1.407(2) . ?
C0BA C7BA 1.369(2) . ?
C1BA C6BA 1.396(2) . ?
C1BA C8AA 1.441(2) . ?
C2BA C9BA 1.375(3) . ?
C3BA C4BA 1.362(3) . ?
C4BA C7BA 1.398(3) . ?
C8BA C9BA 1.394(3) . ?
O1 C2 1.400(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
O0AA S O1AA 111.93(7) . . ?
O0AA S C 106.44(8) . . ?
O0AA S O5AA 114.41(8) . . ?
O1AA S C 105.37(8) . . ?
O5AA S O1AA 112.69(8) . . ?
O5AA S C 105.12(8) . . ?
C5BA N1AA C2AA 108.94(15) . . ?
N3AA C3AA C7AA 112.00(14) . . ?
N1AA C2AA C9AA 108.30(14) . . ?
N1AA C2AA C2BA 128.62(16) . . ?
C2BA C2AA C9AA 123.08(16) . . ?
C4AA N3AA C3AA 118.67(14) . . ?
C4AA N3AA C1AA 119.88(14) . . ?
C1AA N3AA C3AA 121.12(13) . . ?
C7AA C S 112.62(12) . . ?
N3AA C4AA C6BA 122.75(16) . . ?
C1AA C5AA C1BA 120.19(14) . . ?
C3BA C5AA C1AA 117.04(14) . . ?
C3BA C5AA C1BA 122.76(15) . . ?
C6AA C0AA C9AA 131.58(15) . . ?
C5BA C0AA C6AA 122.76(16) . . ?
C5BA C0AA C9AA 105.64(14) . . ?
C8AA C6AA C0AA 127.61(17) . . ?
C8BA C0CA C9AA 118.55(18) . . ?
N3AA C1AA C5AA 119.21(14) . . ?
N3AA C1AA C0BA 119.98(14) . . ?
C0BA C1AA C5AA 120.81(14) . . ?
C2AA C9AA C0AA 106.38(14) . . ?
C0CA C9AA C2AA 118.10(16) . . ?
C0CA C9AA C0AA 135.52(15) . . ?
C C7AA C3AA 114.38(14) . . ?
C7BA C0BA C1AA 119.33(15) . . ?
C5AA C1BA C8AA 121.56(15) . . ?
C6BA C1BA C5AA 116.45(14) . . ?
C6BA C1BA C8AA 121.99(15) . . ?
C9BA C2BA C2AA 117.13(18) . . ?
C4BA C3BA C5AA 121.65(16) . . ?
C3BA C4BA C7BA 120.03(17) . . ?
N1AA C5BA C0AA 110.73(16) . . ?
C4AA C6BA C1BA 121.35(16) . . ?
C0BA C7BA C4BA 120.97(16) . . ?
C6AA C8AA C1BA 124.36(17) . . ?
C0CA C8BA C9BA 122.1(2) . . ?
C2BA C9BA C8BA 121.04(19) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
