# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_1
_audit_block_doi                 10.5517/ccdc.csd.cc21zssm
_database_code_depnum_ccdc_archive 'CCDC 1906431'
loop_
_audit_author_name
_audit_author_address
'Yao Zhou'
;Huaqiao University
China
;
_audit_update_record             
;
2019-03-29 deposited with the CCDC.	2019-08-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H12 I N3 S'
_chemical_formula_sum            'C17 H12 I N3 S'
_chemical_formula_weight         417.26

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   4.1200(5)
_cell_length_b                   14.2279(12)
_cell_length_c                   26.763(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.268(8)
_cell_angle_gamma                90
_cell_volume                     1564.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2467
_cell_measurement_theta_min      4.1690
_cell_measurement_theta_max      27.4400

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.772
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    2.179
_shelx_estimated_absorpt_T_min   0.623
_shelx_estimated_absorpt_T_max   0.722
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.46246
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3060
_diffrn_reflns_av_unetI/netI     0.0561
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.372
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3060
_reflns_number_gt                2798
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0389P)²+0.3511P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3060
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.0989
_refine_ls_wR_factor_gt          0.0962
_refine_ls_goodness_of_fit_ref   1.124
_refine_ls_restrained_S_all      1.124
_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_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 0.68260(11) 0.87476(3) 0.25588(2) 0.04605(15) Uani 1 1 d . . . . .
S1 S 0.0212(5) 1.01709(11) 0.08532(6) 0.0465(4) Uani 1 1 d . . . . .
N1 N 0.3770(12) 0.8793(3) 0.12995(16) 0.0343(11) Uani 1 1 d . . . . .
N2 N 0.5446(13) 0.7432(3) 0.08427(16) 0.0354(11) Uani 1 1 d . . . . .
N3 N 0.7185(13) 0.6640(3) 0.08928(17) 0.0372(11) Uani 1 1 d . . . . .
C1 C 0.304(2) 0.6247(4) -0.0074(2) 0.0525(17) Uani 1 1 d . . . . .
H1 H 0.239461 0.595883 0.021375 0.063 Uiso 1 1 calc R U . . .
C2 C 0.308(2) 0.5741(5) -0.0517(2) 0.060(2) Uani 1 1 d . . . . .
H2 H 0.249081 0.511026 -0.052103 0.072 Uiso 1 1 calc R U . . .
C3 C 0.398(2) 0.6152(5) -0.0944(2) 0.061(2) Uani 1 1 d . . . . .
H3 H 0.390504 0.580923 -0.124026 0.073 Uiso 1 1 calc R U . . .
C4 C 0.498(2) 0.7072(6) -0.0937(2) 0.065(2) Uani 1 1 d . . . . .
H4 H 0.571756 0.734277 -0.122443 0.078 Uiso 1 1 calc R U . . .
C5 C 0.4893(19) 0.7604(5) -0.0496(2) 0.0518(18) Uani 1 1 d . . . . .
H5 H 0.545048 0.823758 -0.049436 0.062 Uiso 1 1 calc R U . . .
C6 C 0.3969(15) 0.7177(4) -0.00620(18) 0.0356(14) Uani 1 1 d . . . . .
C7 C 0.3863(15) 0.7752(4) 0.03987(19) 0.0362(15) Uani 1 1 d . . . . .
C8 C 0.2290(18) 0.8591(4) 0.0418(2) 0.0412(14) Uani 1 1 d . . . . .
H8 H 0.121086 0.883606 0.012969 0.049 Uiso 1 1 calc R U . . .
C9 C 0.2280(16) 0.9097(4) 0.08765(19) 0.0341(13) Uani 1 1 d . . . . .
C10 C 0.063(2) 1.0535(5) 0.1496(2) 0.062(2) Uani 1 1 d . . . . .
H10A H -0.038284 1.113765 0.152875 0.092 Uiso 1 1 calc R U . . .
H10B H 0.289808 1.058001 0.160560 0.092 Uiso 1 1 calc R U . . .
H10C H -0.039929 1.008346 0.169894 0.092 Uiso 1 1 calc R U . . .
C11 C 0.5354(15) 0.7973(4) 0.12853(18) 0.0309(12) Uani 1 1 d . . . . .
C12 C 0.7253(13) 0.7447(4) 0.16438(18) 0.0285(12) Uani 1 1 d . . . . .
C13 C 0.8242(15) 0.7570(4) 0.21574(18) 0.0329(13) Uani 1 1 d . . . . .
C14 C 1.0156(14) 0.6890(4) 0.2398(2) 0.0391(14) Uani 1 1 d . . . . .
H14 H 1.077339 0.695198 0.273775 0.047 Uiso 1 1 calc R U . . .
C15 C 1.1193(17) 0.6095(4) 0.2132(2) 0.0440(15) Uani 1 1 d . . . . .
H15 H 1.251315 0.565134 0.230160 0.053 Uiso 1 1 calc R U . . .
C16 C 1.0321(17) 0.5961(4) 0.1637(2) 0.0408(14) Uani 1 1 d . . . . .
H16 H 1.102366 0.543590 0.146822 0.049 Uiso 1 1 calc R U . . .
C17 C 0.8314(15) 0.6645(4) 0.1386(2) 0.0345(13) 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
I1 C13 2.096(5) . ?
S1 C9 1.748(6) . ?
S1 C10 1.794(6) . ?
N1 C9 1.320(7) . ?
N1 C11 1.340(7) . ?
N2 N3 1.336(7) . ?
N2 C7 1.389(7) . ?
N2 C11 1.415(6) . ?
N3 C17 1.366(7) . ?
C1 C6 1.377(8) . ?
C1 C2 1.387(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.358(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.374(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.406(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.388(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.483(7) . ?
C7 C8 1.361(8) . ?
C8 C9 1.422(8) . ?
C8 H8 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.407(7) . ?
C12 C13 1.415(7) . ?
C12 C17 1.419(7) . ?
C13 C14 1.378(8) . ?
C14 C15 1.419(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.361(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.413(8) . ?
C16 H16 0.9300 . ?

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
C9 S1 C10 101.9(3) . . ?
C9 N1 C11 117.2(5) . . ?
N3 N2 C7 125.2(5) . . ?
N3 N2 C11 114.9(4) . . ?
C7 N2 C11 119.8(5) . . ?
N2 N3 C17 103.5(4) . . ?
C6 C1 C2 119.9(6) . . ?
C6 C1 H1 120.0 . . ?
C2 C1 H1 120.0 . . ?
C3 C2 C1 121.1(7) . . ?
C3 C2 H2 119.5 . . ?
C1 C2 H2 119.5 . . ?
C2 C3 C4 120.0(6) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 C5 119.8(6) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C6 C5 C4 119.6(6) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C1 C6 C5 119.5(5) . . ?
C1 C6 C7 121.7(5) . . ?
C5 C6 C7 118.7(5) . . ?
C8 C7 N2 116.7(5) . . ?
C8 C7 C6 124.0(5) . . ?
N2 C7 C6 119.3(5) . . ?
C7 C8 C9 120.6(5) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
N1 C9 C8 122.9(6) . . ?
N1 C9 S1 120.7(4) . . ?
C8 C9 S1 116.4(4) . . ?
S1 C10 H10A 109.5 . . ?
S1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
S1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C12 133.7(5) . . ?
N1 C11 N2 122.8(5) . . ?
C12 C11 N2 103.5(5) . . ?
C11 C12 C13 134.5(5) . . ?
C11 C12 C17 105.8(5) . . ?
C13 C12 C17 119.7(5) . . ?
C14 C13 C12 118.7(5) . . ?
C14 C13 I1 119.6(4) . . ?
C12 C13 I1 121.7(4) . . ?
C13 C14 C15 120.6(5) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C16 C15 C14 122.2(6) . . ?
C16 C15 H15 118.9 . . ?
C14 C15 H15 118.9 . . ?
C15 C16 C17 117.9(6) . . ?
C15 C16 H16 121.0 . . ?
C17 C16 H16 121.0 . . ?
N3 C17 C16 126.9(5) . . ?
N3 C17 C12 112.3(5) . . ?
C16 C17 C12 120.9(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
C7 N2 N3 C17 178.3(5) . . . . ?
C11 N2 N3 C17 -0.1(6) . . . . ?
C6 C1 C2 C3 -1.0(13) . . . . ?
C1 C2 C3 C4 2.6(14) . . . . ?
C2 C3 C4 C5 -3.9(14) . . . . ?
C3 C4 C5 C6 3.7(13) . . . . ?
C2 C1 C6 C5 0.9(11) . . . . ?
C2 C1 C6 C7 178.0(7) . . . . ?
C4 C5 C6 C1 -2.2(11) . . . . ?
C4 C5 C6 C7 -179.5(7) . . . . ?
N3 N2 C7 C8 -178.1(6) . . . . ?
C11 N2 C7 C8 0.2(8) . . . . ?
N3 N2 C7 C6 2.0(9) . . . . ?
C11 N2 C7 C6 -179.8(5) . . . . ?
C1 C6 C7 C8 -126.4(7) . . . . ?
C5 C6 C7 C8 50.8(9) . . . . ?
C1 C6 C7 N2 53.6(9) . . . . ?
C5 C6 C7 N2 -129.2(6) . . . . ?
N2 C7 C8 C9 -0.5(9) . . . . ?
C6 C7 C8 C9 179.5(6) . . . . ?
C11 N1 C9 C8 0.3(9) . . . . ?
C11 N1 C9 S1 -178.8(4) . . . . ?
C7 C8 C9 N1 0.3(10) . . . . ?
C7 C8 C9 S1 179.4(5) . . . . ?
C10 S1 C9 N1 -3.4(6) . . . . ?
C10 S1 C9 C8 177.5(5) . . . . ?
C9 N1 C11 C12 177.8(6) . . . . ?
C9 N1 C11 N2 -0.6(8) . . . . ?
N3 N2 C11 N1 178.8(5) . . . . ?
C7 N2 C11 N1 0.4(8) . . . . ?
N3 N2 C11 C12 0.0(6) . . . . ?
C7 N2 C11 C12 -178.5(5) . . . . ?
N1 C11 C12 C13 0.1(11) . . . . ?
N2 C11 C12 C13 178.8(6) . . . . ?
N1 C11 C12 C17 -178.5(6) . . . . ?
N2 C11 C12 C17 0.1(6) . . . . ?
C11 C12 C13 C14 179.8(6) . . . . ?
C17 C12 C13 C14 -1.7(8) . . . . ?
C11 C12 C13 I1 0.6(9) . . . . ?
C17 C12 C13 I1 179.1(4) . . . . ?
C12 C13 C14 C15 1.8(9) . . . . ?
I1 C13 C14 C15 -178.9(4) . . . . ?
C13 C14 C15 C16 -1.1(10) . . . . ?
C14 C15 C16 C17 0.0(10) . . . . ?
N2 N3 C17 C16 -179.6(6) . . . . ?
N2 N3 C17 C12 0.2(7) . . . . ?
C15 C16 C17 N3 179.9(6) . . . . ?
C15 C16 C17 C12 0.2(9) . . . . ?
C11 C12 C17 N3 -0.2(7) . . . . ?
C13 C12 C17 N3 -179.1(5) . . . . ?
C11 C12 C17 C16 179.5(5) . . . . ?
C13 C12 C17 C16 0.7(8) . . . . ?

_refine_diff_density_max         0.776
_refine_diff_density_min         -0.868
_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_exp_5898
_audit_block_doi                 10.5517/ccdc.csd.cc20y0ff
_database_code_depnum_ccdc_archive 'CCDC 1874924'
loop_
_audit_author_name
_audit_author_address
'Yao Zhou'
;Huaqiao University
China
;
_audit_update_record             
;
2018-10-23 deposited with the CCDC.	2019-08-09 downloaded from the CCDC.
;
_audit_creation_date             2018-10-23
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_chemical_formula_moiety         '0.5(C19 H17 N O S2)'
_chemical_formula_sum            'C9.5 H8.5 N0.5 O0.5 S'
_chemical_formula_weight         169.74
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y+1/2,-z+1/2
4 -x+1/2,-y,z+1/2
5 -x,-y,-z
6 -x-1/2,y-1/2,z
7 x,-y-1/2,z-1/2
8 x-1/2,y,-z-1/2

_symmetry_Int_Tables_number      61
_cell_length_a                   10.1327(10)
_cell_length_b                   12.0719(14)
_cell_length_c                   28.967(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3543.3(7)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    1952
_cell_measurement_theta_max      27.7390
_cell_measurement_theta_min      4.0270
_exptl_absorpt_coefficient_mu    0.304
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.09698
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.2727
_exptl_crystal_F_000             1426.4823
_diffrn_reflns_av_R_equivalents  0.0916
_diffrn_reflns_av_unetI/netI     0.1500
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            10871
_diffrn_reflns_theta_full        24.9985
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.37
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0606
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9981
_diffrn_measured_fraction_theta_max 0.9981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -10.00  62.90   0.30   10.50    --   15.49  77.00 150.00  243
  2  ω    -41.00  -2.00   0.30   10.50    --  -16.28  19.00 -30.00  130
  3  ω    -17.00  23.20   0.30   10.50    --  -16.28 -99.00  30.00  134
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0610034000
_diffrn_orient_matrix_UB_12      -0.0131281000
_diffrn_orient_matrix_UB_13      0.0106809000
_diffrn_orient_matrix_UB_21      -0.0243822000
_diffrn_orient_matrix_UB_22      0.0203635000
_diffrn_orient_matrix_UB_23      0.0213500000
_diffrn_orient_matrix_UB_31      -0.0241773000
_diffrn_orient_matrix_UB_32      -0.0535234000
_diffrn_orient_matrix_UB_33      0.0054531000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              0
_reflns_limit_k_max              14
_reflns_limit_k_min              0
_reflns_limit_l_max              34
_reflns_limit_l_min              0
_reflns_number_gt                1790
_reflns_number_total             3111
_reflns_odcompleteness_completeness 99.54
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.8745
_refine_diff_density_min         -0.5269
_refine_diff_density_rms         0.1398
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             6.0492
_refine_ls_goodness_of_fit_ref   0.8505
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    28
_exptl_crystal_description       block
_cell_measurement_temperature    298
_diffrn_ambient_temperature      298
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3111
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1198
_refine_ls_R_factor_gt           0.0634
_refine_ls_restrained_S_all      0.8505
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1463
_refine_ls_wR_factor_ref         0.1848
_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:
 C00C(H00C), C00H(H00H), C00K(H00K), C00A(H00A), C00I(H00I), C00J(H00J),
 C00G(H00G), C009(H009)
2.b Idealised Me refined as rotating group:
 C00L(H00b,H00d,H00e), C00M(H00f,H00l,H00m), C00N(H00n,H00o,H00p)
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
S001 S 0.69149(11) 0.55648(9) 0.66998(4) 0.0486(4) Uani 1.000000 .
S002 S 0.43099(12) 0.59058(10) 0.72202(3) 0.0520(4) Uani 1.000000 .
O003 O 0.4941(3) 0.5033(2) 0.56520(9) 0.0511(8) Uani 1.000000 .
C004 C 0.4617(4) 0.6176(3) 0.63026(12) 0.0313(9) Uani 1.000000 .
C005 C 0.5245(4) 0.5908(3) 0.58392(12) 0.0335(9) Uani 1.000000 .
C006 C 0.6151(4) 0.6713(3) 0.56164(12) 0.0327(9) Uani 1.000000 .
C007 C 0.5208(4) 0.5934(3) 0.67010(12) 0.0365(10) Uani 1.000000 .
C008 C 0.3239(4) 0.6612(3) 0.62624(11) 0.0349(10) Uani 1.000000 .
C009 C 0.6621(4) 0.6488(3) 0.51764(12) 0.0430(11) Uani 1.000000 .
C00A C 0.6532(4) 0.7685(3) 0.58384(13) 0.0432(10) Uani 1.000000 .
C00B C 0.2880(4) 0.7673(3) 0.64311(12) 0.0392(10) Uani 1.000000 .
C00C C 0.2276(4) 0.6010(3) 0.60374(13) 0.0411(10) Uani 1.000000 .
N00D N 0.4607(5) 0.8930(3) 0.68262(15) 0.0756(13) Uani 1.000000 .
C00E C 0.0989(4) 0.6383(3) 0.59785(15) 0.0496(11) Uani 1.000000 .
C00F C 0.3853(5) 0.8359(4) 0.66551(15) 0.0501(11) Uani 1.000000 .
C00G C 0.7479(5) 0.7213(3) 0.49682(13) 0.0548(12) Uani 1.000000 .
C00H C 0.0684(5) 0.7425(4) 0.61475(14) 0.0536(12) Uani 1.000000 .
C00I C 0.7400(4) 0.8406(3) 0.56223(15) 0.0501(11) Uani 1.000000 .
C00J C 0.7885(4) 0.8177(3) 0.51919(15) 0.0521(12) Uani 1.000000 .
C00K C 0.1599(5) 0.8057(3) 0.63711(14) 0.0518(12) Uani 1.000000 .
C00L C 0.6904(5) 0.4260(4) 0.70049(16) 0.0678(14) Uani 1.000000 .
C00M C 0.5393(5) 0.6545(4) 0.76323(14) 0.0660(14) Uani 1.000000 .
C00N C -0.0009(6) 0.5695(4) 0.57254(19) 0.0814(17) Uani 1.000000 .
H00C H 0.2500(4) 0.5319(3) 0.59190(13) 0.0493(12) Uiso 1.000000 R
H00H H -0.0166(5) 0.7701(4) 0.61075(14) 0.0644(14) Uiso 1.000000 R
H00K H 0.1364(5) 0.8751(3) 0.64841(14) 0.0621(14) Uiso 1.000000 R
H00A H 0.6206(4) 0.7850(3) 0.61305(13) 0.0519(12) Uiso 1.000000 R
H00I H 0.7656(4) 0.9053(3) 0.57718(15) 0.0601(14) Uiso 1.000000 R
H00J H 0.8477(4) 0.8658(3) 0.50505(15) 0.0626(14) Uiso 1.000000 R
H00G H 0.7793(5) 0.7058(3) 0.46736(13) 0.0658(15) Uiso 1.000000 R
H009 H 0.6355(4) 0.5849(3) 0.50230(12) 0.0516(13) Uiso 1.000000 R
H00b H 0.648(3) 0.3707(8) 0.6818(5) 0.102(2) Uiso 1.000000 GR
H00d H 0.7795(5) 0.4036(14) 0.7068(10) 0.102(2) Uiso 1.000000 GR
H00e H 0.643(3) 0.4343(8) 0.7290(6) 0.102(2) Uiso 1.000000 GR
H00f H 0.551(2) 0.7312(7) 0.7554(6) 0.099(2) Uiso 1.000000 GR
H00l H 0.5015(15) 0.649(2) 0.7935(2) 0.099(2) Uiso 1.000000 GR
H00m H 0.6233(11) 0.6177(16) 0.7627(7) 0.099(2) Uiso 1.000000 GR
H00n H 0.009(2) 0.580(2) 0.53991(19) 0.122(3) Uiso 1.000000 GR
H00o H 0.012(2) 0.4927(5) 0.5798(10) 0.122(3) Uiso 1.000000 GR
H00p H -0.0882(6) 0.591(2) 0.5817(9) 0.122(3) Uiso 1.000000 GR


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
S001 C007 1.785(4) . ?
S001 C00L 1.806(4) . ?
S002 C007 1.759(4) . ?
S002 C00M 1.795(4) . ?
O003 C005 1.227(4) . ?
C004 C005 1.521(5) . ?
C004 C007 1.333(5) . ?
C004 C008 1.496(5) . ?
C005 C006 1.484(5) . ?
C006 C009 1.387(5) . ?
C006 C00A 1.393(5) . ?
C008 C00B 1.418(5) . ?
C008 C00C 1.380(5) . ?
C009 C00G 1.373(5) . ?
C009 H009 0.9300 . ?
C00A C00I 1.387(5) . ?
C00A H00A 0.9300 . ?
C00B C00F 1.442(6) . ?
C00B C00K 1.389(6) . ?
C00C C00E 1.391(6) . ?
C00C H00C 0.9300 . ?
N00D C00F 1.142(5) . ?
C00E C00H 1.385(6) . ?
C00E C00N 1.500(6) . ?
C00G C00J 1.395(6) . ?
C00G H00G 0.9300 . ?
C00H C00K 1.364(6) . ?
C00H H00H 0.9300 . ?
C00I C00J 1.368(6) . ?
C00I H00I 0.9300 . ?
C00J H00J 0.9300 . ?
C00K H00K 0.9300 . ?
C00L H00b 0.9600 . ?
C00L H00d 0.9600 . ?
C00L H00e 0.9600 . ?
C00M H00f 0.9600 . ?
C00M H00l 0.9600 . ?
C00M H00m 0.9600 . ?
C00N H00n 0.9600 . ?
C00N H00o 0.9600 . ?
C00N H00p 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
C00L S001 C007 102.2(2) . . ?
C00M S002 C007 104.1(2) . . ?
C007 C004 C005 121.9(3) . . ?
C008 C004 C005 113.4(3) . . ?
C008 C004 C007 124.3(3) . . ?
C004 C005 O003 117.9(3) . . ?
C006 C005 O003 121.8(3) . . ?
C006 C005 C004 120.2(3) . . ?
C009 C006 C005 118.9(3) . . ?
C00A C006 C005 121.5(3) . . ?
C00A C006 C009 119.6(4) . . ?
S002 C007 S001 119.9(2) . . ?
C004 C007 S001 119.2(3) . . ?
C004 C007 S002 120.8(3) . . ?
C00B C008 C004 122.0(3) . . ?
C00C C008 C004 120.7(3) . . ?
C00C C008 C00B 117.2(4) . . ?
C00G C009 C006 119.8(3) . . ?
H009 C009 C006 120.1(2) . . ?
H009 C009 C00G 120.1(2) . . ?
C00I C00A C006 119.8(4) . . ?
H00A C00A C006 120.1(2) . . ?
H00A C00A C00I 120.1(2) . . ?
C00F C00B C008 119.9(4) . . ?
C00K C00B C008 119.9(4) . . ?
C00K C00B C00F 120.2(4) . . ?
C00E C00C C008 123.4(4) . . ?
H00C C00C C008 118.3(2) . . ?
H00C C00C C00E 118.3(2) . . ?
C00H C00E C00C 117.4(4) . . ?
C00N C00E C00C 120.8(4) . . ?
C00N C00E C00H 121.7(4) . . ?
N00D C00F C00B 177.9(5) . . ?
C00J C00G C009 121.0(4) . . ?
H00G C00G C009 119.5(2) . . ?
H00G C00G C00J 119.5(2) . . ?
C00K C00H C00E 121.6(4) . . ?
H00H C00H C00E 119.2(3) . . ?
H00H C00H C00K 119.2(3) . . ?
C00J C00I C00A 120.8(4) . . ?
H00I C00I C00A 119.6(2) . . ?
H00I C00I C00J 119.6(2) . . ?
C00I C00J C00G 119.1(4) . . ?
H00J C00J C00G 120.5(2) . . ?
H00J C00J C00I 120.5(2) . . ?
C00H C00K C00B 120.5(4) . . ?
H00K C00K C00B 119.7(2) . . ?
H00K C00K C00H 119.7(3) . . ?
H00b C00L S001 109.5 . . ?
H00d C00L S001 109.5 . . ?
H00d C00L H00b 109.5 . . ?
H00e C00L S001 109.5 . . ?
H00e C00L H00b 109.5 . . ?
H00e C00L H00d 109.5 . . ?
H00f C00M S002 109.5 . . ?
H00l C00M S002 109.5 . . ?
H00l C00M H00f 109.5 . . ?
H00m C00M S002 109.5 . . ?
H00m C00M H00f 109.5 . . ?
H00m C00M H00l 109.5 . . ?
H00n C00N C00E 109.5 . . ?
H00o C00N C00E 109.5 . . ?
H00o C00N H00n 109.5 . . ?
H00p C00N C00E 109.5 . . ?
H00p C00N H00n 109.5 . . ?
H00p C00N H00o 109.5 . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.657
_oxdiff_exptl_absorpt_empirical_full_min 0.354
