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

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

data_sa4848a
_database_code_depnum_ccdc_archive 'CCDC 1501611'
_audit_update_record             
;
2016-08-30 deposited with the CCDC.
2017-10-20 downloaded from the CCDC.
;
_audit_creation_date             2016-06-06
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H13 N S'
_chemical_formula_sum            'C17 H13 N S'
_chemical_formula_weight         263.34
_chemical_absolute_configuration ad
_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'
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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   5.4797(4)
_cell_length_b                   9.5670(7)
_cell_length_c                   24.6309(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1291.26(16)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4325
_cell_measurement_temperature    173.1500
_cell_measurement_theta_max      27.4691
_cell_measurement_theta_min      2.2838
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.234
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85076
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.389
_exptl_crystal_size_mid          0.324
_exptl_crystal_size_min          0.171
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5038
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.468
_diffrn_reflns_theta_min         3.270
_diffrn_ambient_temperature      173.1500
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_details      
;
scan:
	Number of images: 360
	           Slice: -110.0000 - 70.0000
	     Image width: 0.5000
	        Exp time: 10.0000
	   Rotation axis: Omega
	           Omega: 0.0000
	             Chi: 45.0000
	             Phi: 90.0000
	             XTD: 45.1096
	          2theta: -19.8653
;
_diffrn_measurement_device       
;
Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_device_details 
;
AFC10: Fixed Chi 2 circle
;
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_number_total             1739
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      -0.1679
_diffrn_orient_matrix_UB_12      0.0401
_diffrn_orient_matrix_UB_13      0.0593
_diffrn_orient_matrix_UB_21      -0.0265
_diffrn_orient_matrix_UB_22      -0.1009
_diffrn_orient_matrix_UB_23      -0.0067
_diffrn_orient_matrix_UB_31      0.0122
_diffrn_orient_matrix_UB_32      -0.0057
_diffrn_orient_matrix_UB_33      0.0383
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  'Graphite Monochromator'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           30.0000
_diffrn_source_power             1.5000
_diffrn_source_voltage           50.0000
_diffrn_special_details          
;
 ?
;
_reflns_Friedel_coverage         0.612
_reflns_Friedel_fraction_full    0.910
_reflns_Friedel_fraction_max     0.869
_reflns_number_gt                2653
_reflns_number_total             2767
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2014)'
_computing_structure_solution    
;
'SHELXT (Sheldrick, 2014)'
;
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 912 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.09(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2767
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0392
_refine_ls_restrained_S_all      1.132
_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)+(0.0326P)²+0.3727P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0857
_refine_ls_wR_factor_ref         0.0878
_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), C8(H8), C13(H13), C14(H14), C15(H15),
 C16(H16), C17(H17)
2.b Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_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
S1 S 0.16303(12) 0.35753(7) 0.53614(3) 0.02969(18) Uani 1 1 d . . . . .
N1 N 0.2871(4) 0.2420(2) 0.63897(9) 0.0295(5) Uani 1 1 d . . . . .
C1 C 0.4697(5) 0.2730(3) 0.67627(11) 0.0285(6) Uani 1 1 d . . . . .
C2 C 0.5173(5) 0.2100(3) 0.72622(11) 0.0327(6) Uani 1 1 d . . . . .
H2 H 0.4209 0.1373 0.7391 0.039 Uiso 1 1 calc R . . . .
C3 C 0.7137(5) 0.2600(3) 0.75583(11) 0.0354(7) Uani 1 1 d . . . . .
H3 H 0.7486 0.2203 0.7894 0.043 Uiso 1 1 calc R . . . .
C4 C 0.8607(5) 0.3686(3) 0.73654(11) 0.0336(6) Uani 1 1 d . . . . .
H4 H 0.9912 0.3998 0.7574 0.040 Uiso 1 1 calc R . . . .
C5 C 0.8141(5) 0.4303(3) 0.68671(11) 0.0301(6) Uani 1 1 d . . . . .
H5 H 0.9144 0.5014 0.6738 0.036 Uiso 1 1 calc R . . . .
C6 C 0.6148(5) 0.3848(3) 0.65595(10) 0.0266(6) Uani 1 1 d . . . . .
C7 C 0.5124(5) 0.4208(3) 0.60369(10) 0.0264(6) Uani 1 1 d . . . . .
C8 C 0.5413(5) 0.5130(3) 0.55860(11) 0.0274(6) Uani 1 1 d . . . . .
H8 H 0.6637 0.5801 0.5563 0.033 Uiso 1 1 calc R . . . .
C9 C 0.3700(5) 0.4922(3) 0.51931(10) 0.0270(6) Uani 1 1 d . . . . .
C10 C 0.3156(5) 0.3321(3) 0.59630(10) 0.0272(5) Uani 1 1 d . . . . .
C11 C 0.1011(5) 0.1350(3) 0.64360(11) 0.0336(6) Uani 1 1 d . . . . .
H11A H 0.1522 0.0530 0.6243 0.050 Uiso 1 1 calc GR . . . .
H11B H -0.0490 0.1689 0.6284 0.050 Uiso 1 1 calc GR . . . .
H11C H 0.0769 0.1122 0.6812 0.050 Uiso 1 1 calc GR . . . .
C12 C 0.3433(5) 0.5657(3) 0.46716(10) 0.0258(5) Uani 1 1 d . . . . .
C13 C 0.5160(5) 0.6658(3) 0.45142(10) 0.0285(6) Uani 1 1 d . . . . .
H13 H 0.6445 0.6870 0.4747 0.034 Uiso 1 1 calc R . . . .
C14 C 0.4992(5) 0.7344(3) 0.40171(11) 0.0302(6) Uani 1 1 d . . . . .
H14 H 0.6157 0.8006 0.3921 0.036 Uiso 1 1 calc R . . . .
C15 C 0.3080(6) 0.7037(3) 0.36645(11) 0.0319(6) Uani 1 1 d . . . . .
H15 H 0.2970 0.7482 0.3330 0.038 Uiso 1 1 calc R . . . .
C16 C 0.1352(5) 0.6069(3) 0.38167(11) 0.0342(6) Uani 1 1 d . . . . .
H16 H 0.0065 0.5867 0.3583 0.041 Uiso 1 1 calc R . . . .
C17 C 0.1506(5) 0.5389(3) 0.43145(11) 0.0317(6) Uani 1 1 d . . . . .
H17 H 0.0309 0.4746 0.4411 0.038 Uiso 1 1 calc R . . . .


_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 C9 1.766(3) . ?
S1 C10 1.719(3) . ?
N1 C1 1.391(4) . ?
N1 C10 1.368(3) . ?
N1 C11 1.449(3) . ?
C1 C2 1.394(4) . ?
C1 C6 1.423(4) . ?
C2 H2 0.9300 . ?
C2 C3 1.385(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.398(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.386(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.399(4) . ?
C6 C7 1.446(4) . ?
C7 C8 1.427(4) . ?
C7 C10 1.384(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.363(4) . ?
C9 C12 1.472(4) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.402(4) . ?
C12 C17 1.398(4) . ?
C13 H13 0.9300 . ?
C13 C14 1.392(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.392(4) . ?
C15 H15 0.9300 . ?
C15 C16 1.376(4) . ?
C16 H16 0.9300 . ?
C16 C17 1.391(4) . ?
C17 H17 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
C10 S1 C9 89.62(13) . . ?
C1 N1 C11 127.2(2) . . ?
C10 N1 C1 106.9(2) . . ?
C10 N1 C11 125.9(2) . . ?
N1 C1 C2 128.7(3) . . ?
N1 C1 C6 109.3(2) . . ?
C2 C1 C6 122.0(3) . . ?
C1 C2 H2 121.3 . . ?
C3 C2 C1 117.4(3) . . ?
C3 C2 H2 121.3 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.7(3) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 H4 119.6 . . ?
C5 C4 C3 120.8(3) . . ?
C5 C4 H4 119.6 . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C6 119.4(3) . . ?
C6 C5 H5 120.3 . . ?
C1 C6 C7 106.0(2) . . ?
C5 C6 C1 118.7(2) . . ?
C5 C6 C7 135.3(2) . . ?
C8 C7 C6 142.8(2) . . ?
C10 C7 C6 105.9(2) . . ?
C10 C7 C8 111.3(2) . . ?
C7 C8 H8 123.6 . . ?
C9 C8 C7 112.7(2) . . ?
C9 C8 H8 123.6 . . ?
C8 C9 S1 112.5(2) . . ?
C8 C9 C12 128.2(3) . . ?
C12 C9 S1 119.30(19) . . ?
N1 C10 S1 134.1(2) . . ?
N1 C10 C7 112.0(2) . . ?
C7 C10 S1 113.92(19) . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 C9 120.0(2) . . ?
C17 C12 C9 122.5(2) . . ?
C17 C12 C13 117.5(2) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 C12 121.4(2) . . ?
C14 C13 H13 119.3 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 119.9(3) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 120.3 . . ?
C16 C15 C14 119.3(3) . . ?
C16 C15 H15 120.3 . . ?
C15 C16 H16 119.6 . . ?
C15 C16 C17 120.9(3) . . ?
C17 C16 H16 119.6 . . ?
C12 C17 H17 119.5 . . ?
C16 C17 C12 121.0(3) . . ?
C16 C17 H17 119.5 . . ?

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 C9 C12 C13 -175.45(19) . . . . ?
S1 C9 C12 C17 3.9(3) . . . . ?
N1 C1 C2 C3 179.4(3) . . . . ?
N1 C1 C6 C5 -178.3(2) . . . . ?
N1 C1 C6 C7 -0.3(3) . . . . ?
C1 N1 C10 S1 -179.9(2) . . . . ?
C1 N1 C10 C7 0.7(3) . . . . ?
C1 C2 C3 C4 -0.5(4) . . . . ?
C1 C6 C7 C8 -179.7(3) . . . . ?
C1 C6 C7 C10 0.7(3) . . . . ?
C2 C1 C6 C5 1.4(4) . . . . ?
C2 C1 C6 C7 179.4(2) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C3 C4 C5 C6 1.2(4) . . . . ?
C4 C5 C6 C1 -1.8(4) . . . . ?
C4 C5 C6 C7 -179.1(3) . . . . ?
C5 C6 C7 C8 -2.1(6) . . . . ?
C5 C6 C7 C10 178.2(3) . . . . ?
C6 C1 C2 C3 -0.2(4) . . . . ?
C6 C7 C8 C9 -179.6(3) . . . . ?
C6 C7 C10 S1 179.57(18) . . . . ?
C6 C7 C10 N1 -0.9(3) . . . . ?
C7 C8 C9 S1 0.2(3) . . . . ?
C7 C8 C9 C12 -179.3(2) . . . . ?
C8 C7 C10 S1 -0.2(3) . . . . ?
C8 C7 C10 N1 179.4(2) . . . . ?
C8 C9 C12 C13 4.0(4) . . . . ?
C8 C9 C12 C17 -176.6(3) . . . . ?
C9 S1 C10 N1 -179.2(3) . . . . ?
C9 S1 C10 C7 0.3(2) . . . . ?
C9 C12 C13 C14 178.3(2) . . . . ?
C9 C12 C17 C16 -177.8(2) . . . . ?
C10 S1 C9 C8 -0.3(2) . . . . ?
C10 S1 C9 C12 179.3(2) . . . . ?
C10 N1 C1 C2 -179.9(3) . . . . ?
C10 N1 C1 C6 -0.2(3) . . . . ?
C10 C7 C8 C9 0.0(3) . . . . ?
C11 N1 C1 C2 0.0(5) . . . . ?
C11 N1 C1 C6 179.7(2) . . . . ?
C11 N1 C10 S1 0.3(4) . . . . ?
C11 N1 C10 C7 -179.2(2) . . . . ?
C12 C13 C14 C15 -0.1(4) . . . . ?
C13 C12 C17 C16 1.6(4) . . . . ?
C13 C14 C15 C16 0.9(4) . . . . ?
C14 C15 C16 C17 -0.5(4) . . . . ?
C15 C16 C17 C12 -0.8(4) . . . . ?
C17 C12 C13 C14 -1.1(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_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_mx5776
_database_code_depnum_ccdc_archive 'CCDC 1542308'
_audit_update_record             
;
2017-04-05 deposited with the CCDC.
2017-10-20 downloaded from the CCDC.
;
_audit_creation_date             2017-04-05
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5335)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H12 I N S'
_chemical_formula_sum            'C17 H12 I N S'
_chemical_formula_weight         389.24
_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'
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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   6.2817(13)
_cell_length_b                   19.730(4)
_cell_length_c                   23.695(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2936.7(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8126
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.4733
_cell_measurement_theta_min      0.8594
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.311
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.75948
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            Colorless
_exptl_crystal_density_diffrn    1.761
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       Plate
_exptl_crystal_F_000             1520
_exptl_crystal_size_max          0.254
_exptl_crystal_size_mid          0.113
_exptl_crystal_size_min          0.042
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0426
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            12514
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.487
_diffrn_reflns_theta_min         2.064
_diffrn_ambient_temperature      173(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   Confocal
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3150
_reflns_number_total             3329
_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       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.483
_refine_diff_density_min         -0.659
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.162
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         3329
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0514
_refine_ls_R_factor_gt           0.0469
_refine_ls_restrained_S_all      1.162
_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)+(0.0240P)²+7.8220P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0900
_refine_ls_wR_factor_ref         0.0923
_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), C5(H5), C6(H6), C8(H8), C13(H13), C14(H14), C15(H15), C16(H16)
2.b Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.96657(4) 0.17181(2) 0.31064(2) 0.03724(11) Uani 1 1 d . . . . .
S1 S 0.1249(2) 0.53392(5) 0.32790(5) 0.0354(2) Uani 1 1 d . . . . .
N1 N -0.1065(6) 0.48207(17) 0.42173(14) 0.0317(8) Uani 1 1 d . . . . .
C17 C -0.2754(8) 0.5320(2) 0.4271(2) 0.0422(11) Uani 1 1 d . . . . .
H17A H -0.246206 0.569703 0.402663 0.063 Uiso 1 1 calc GR . . . .
H17B H -0.282774 0.547473 0.465437 0.063 Uiso 1 1 calc GR . . . .
H17C H -0.408769 0.511808 0.416656 0.063 Uiso 1 1 calc GR . . . .
C1 C 0.7630(6) 0.2559(2) 0.31933(16) 0.0278(8) Uani 1 1 d . . . . .
C2 C 0.5572(6) 0.2449(2) 0.33853(16) 0.0284(8) Uani 1 1 d . . . . .
H2 H 0.509056 0.201108 0.345541 0.034 Uiso 1 1 calc R . . . .
C3 C 0.4245(6) 0.2999(2) 0.34712(16) 0.0273(8) Uani 1 1 d . . . . .
H3 H 0.286605 0.292633 0.360081 0.033 Uiso 1 1 calc R . . . .
C4 C 0.4924(6) 0.3660(2) 0.33682(16) 0.0261(8) Uani 1 1 d . . . . .
C5 C 0.6996(6) 0.3753(2) 0.31603(16) 0.0295(9) Uani 1 1 d . . . . .
H5 H 0.747459 0.418863 0.308195 0.035 Uiso 1 1 calc R . . . .
C6 C 0.8347(7) 0.3206(2) 0.30692(16) 0.0311(9) Uani 1 1 d . . . . .
H6 H 0.971038 0.327362 0.292720 0.037 Uiso 1 1 calc R . . . .
C7 C 0.3454(6) 0.4234(2) 0.34531(16) 0.0265(8) Uani 1 1 d . . . . .
C8 C 0.3320(7) 0.4790(2) 0.31107(17) 0.0340(9) Uani 1 1 d . . . . .
H8 H 0.425511 0.486829 0.281343 0.041 Uiso 1 1 calc R . . . .
C9 C 0.0527(7) 0.4811(2) 0.38250(16) 0.0293(8) Uani 1 1 d . . . . .
C10 C 0.1826(6) 0.42528(19) 0.38830(16) 0.0257(8) Uani 1 1 d . . . . .
C11 C 0.1014(6) 0.3892(2) 0.43665(16) 0.0271(8) Uani 1 1 d . . . . .
C12 C -0.0787(7) 0.4256(2) 0.45552(17) 0.0312(9) Uani 1 1 d . . . . .
C13 C -0.2011(7) 0.4045(2) 0.5016(2) 0.0405(11) Uani 1 1 d . . . . .
H13 H -0.322026 0.428244 0.512621 0.049 Uiso 1 1 calc R . . . .
C14 C -0.1362(8) 0.3470(2) 0.53021(19) 0.0408(11) Uani 1 1 d . . . . .
H14 H -0.214853 0.331703 0.560917 0.049 Uiso 1 1 calc R . . . .
C15 C 0.0461(8) 0.3117(2) 0.51356(19) 0.0396(11) Uani 1 1 d . . . . .
H15 H 0.089281 0.274085 0.534224 0.048 Uiso 1 1 calc R . . . .
C16 C 0.1633(7) 0.3314(2) 0.46724(17) 0.0318(9) Uani 1 1 d . . . . .
H16 H 0.282314 0.306629 0.456275 0.038 Uiso 1 1 calc R . . . .


_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 C1 2.105(4) . ?
S1 C8 1.739(5) . ?
S1 C9 1.722(4) . ?
N1 C17 1.453(5) . ?
N1 C9 1.366(5) . ?
N1 C12 1.384(5) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C1 C2 1.388(5) . ?
C1 C6 1.386(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.384(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.394(6) . ?
C4 C5 1.404(5) . ?
C4 C7 1.475(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.389(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.368(6) . ?
C7 C10 1.444(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.377(5) . ?
C10 C11 1.442(5) . ?
C11 C12 1.412(6) . ?
C11 C16 1.407(6) . ?
C12 C13 1.399(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.381(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.398(7) . ?
C15 H15 0.9300 . ?
C15 C16 1.377(6) . ?
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 C8 89.6(2) . . ?
C9 N1 C17 127.1(4) . . ?
C9 N1 C12 106.9(3) . . ?
C12 N1 C17 126.0(4) . . ?
N1 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
N1 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C2 C1 I1 118.3(3) . . ?
C6 C1 I1 120.5(3) . . ?
C6 C1 C2 121.1(4) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.1(4) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 119.2 . . ?
C2 C3 C4 121.6(4) . . ?
C4 C3 H3 119.2 . . ?
C3 C4 C5 117.8(4) . . ?
C3 C4 C7 120.2(3) . . ?
C5 C4 C7 121.9(4) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 C4 121.3(4) . . ?
C6 C5 H5 119.3 . . ?
C1 C6 C5 119.0(4) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C8 C7 C4 125.0(4) . . ?
C8 C7 C10 110.7(4) . . ?
C10 C7 C4 124.0(4) . . ?
S1 C8 H8 122.9 . . ?
C7 C8 S1 114.2(3) . . ?
C7 C8 H8 122.9 . . ?
N1 C9 S1 134.1(3) . . ?
N1 C9 C10 112.2(4) . . ?
C10 C9 S1 113.7(3) . . ?
C9 C10 C7 111.7(4) . . ?
C9 C10 C11 105.3(3) . . ?
C11 C10 C7 143.0(4) . . ?
C12 C11 C10 106.6(3) . . ?
C16 C11 C10 135.4(4) . . ?
C16 C11 C12 118.0(4) . . ?
N1 C12 C11 109.1(4) . . ?
N1 C12 C13 128.5(4) . . ?
C13 C12 C11 122.4(4) . . ?
C12 C13 H13 121.2 . . ?
C14 C13 C12 117.7(4) . . ?
C14 C13 H13 121.2 . . ?
C13 C14 H14 119.6 . . ?
C13 C14 C15 120.8(4) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 119.2 . . ?
C16 C15 C14 121.5(4) . . ?
C16 C15 H15 119.2 . . ?
C11 C16 H16 120.3 . . ?
C15 C16 C11 119.4(4) . . ?
C15 C16 H16 120.3 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
