# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# 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_id118_0m_a_pl
_database_code_depnum_ccdc_archive 'CCDC 1946322'
loop_
_audit_author_name
_audit_author_address
'Yunus Zorlu' 'Gebze Technical University'
_audit_update_record             
;
2019-08-09 deposited with the CCDC.	2020-07-31 downloaded from the CCDC.
;
_audit_creation_date             2019-03-08
_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         'C30 H36 O2 S2'
_chemical_formula_sum            'C30 H36 O2 S2'
_chemical_formula_weight         492.71
_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'
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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   60.991(12)
_cell_length_b                   7.6857(18)
_cell_length_c                   5.7799(13)
_cell_angle_alpha                90
_cell_angle_beta                 92.122(16)
_cell_angle_gamma                90
_cell_volume                     2707.5(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4606
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.34
_cell_measurement_theta_min      2.66
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_T_max  0.6104
_exptl_absorpt_correction_T_min  0.4758
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1440 before and 0.0839 after correction.
The Ratio of minimum to maximum transmission is 0.8081.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.209
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.042
_exptl_crystal_size_min          0.033
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1058
_diffrn_reflns_av_unetI/netI     0.1037
_diffrn_reflns_Laue_measured_fraction_full 0.945
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       71
_diffrn_reflns_limit_h_min       -72
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_number            9352
_diffrn_reflns_point_group_measured_fraction_full 0.945
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        24.990
_diffrn_reflns_theta_max         24.990
_diffrn_reflns_theta_min         2.005
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.945
_diffrn_measured_fraction_theta_max 0.945
_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                1688
_reflns_number_total             2264
_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 V8.35A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.35A (?, 2016)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.137
_refine_diff_density_min         -0.892
_refine_diff_density_rms         0.198
_refine_ls_extinction_coef       2.1(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.743
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2264
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.2107
_refine_ls_R_factor_gt           0.1840
_refine_ls_restrained_S_all      1.741
_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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4296
_refine_ls_wR_factor_ref         0.4418
_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. Restrained distances
 C18-C17 = C17-C16 = C16-C15 = C15-C14 = C14-C13 = C13-C12
 1.51 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C5 \\sim C4: within 2A with sigma of 0.02 and sigma for terminal atoms of 0.002
S1 \\sim C7: within 2A with sigma of 0.02 and sigma for terminal atoms of 0.002
4.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,
 H16B), C17(H17A,H17B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6)
4.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_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
S1 S 0.26458(3) 0.3593(2) 0.7972(3) 0.0524(14) Uani 1 1 d . U . . .
O2 O 0.14809(15) 0.1646(12) 0.2373(16) 0.112(3) Uani 1 1 d . . . . .
C1 C 0.17724(18) 0.2457(15) 0.4797(18) 0.086(3) Uani 1 1 d . . . . .
C2 C 0.18403(17) 0.3223(11) 0.6838(15) 0.064(3) Uani 1 1 d . . . . .
H2 H 0.173296 0.359705 0.782651 0.077 Uiso 1 1 calc R . . . .
C3 C 0.20590(13) 0.3480(8) 0.7540(13) 0.040(2) Uani 1 1 d . . . . .
H3 H 0.209958 0.400062 0.894318 0.049 Uiso 1 1 calc R . . . .
C4 C 0.22209(13) 0.2868(10) 0.5902(12) 0.051(2) Uani 1 1 d . U . . .
C5 C 0.28581(13) 0.2950(10) 0.6239(14) 0.055(2) Uani 1 1 d . U . . .
C6 C 0.30748(13) 0.3135(11) 0.6691(16) 0.059(2) Uani 1 1 d . . . . .
H6 H 0.312221 0.368115 0.805547 0.071 Uiso 1 1 calc R . . . .
C7 C 0.24527(12) 0.2870(8) 0.5939(11) 0.045(2) Uani 1 1 d . U . . .
C11 C 0.1532(2) 0.2260(14) 0.4250(18) 0.086(3) Uani 1 1 d . . . . .
C12 C 0.13722(18) 0.273(2) 0.601(2) 0.104(4) Uani 1 1 d D . . . .
H12A H 0.141878 0.220948 0.747672 0.125 Uiso 1 1 calc R . . . .
H12B H 0.137541 0.398658 0.622028 0.125 Uiso 1 1 calc R . . . .
C13 C 0.11440(17) 0.220(2) 0.546(2) 0.116(4) Uani 1 1 d D . . . .
H13A H 0.113684 0.094107 0.535369 0.139 Uiso 1 1 calc R . . . .
H13B H 0.109766 0.267347 0.396192 0.139 Uiso 1 1 calc R . . . .
C14 C 0.09884(18) 0.2831(19) 0.729(2) 0.118(5) Uani 1 1 d D . . . .
H14A H 0.104452 0.246418 0.880878 0.142 Uiso 1 1 calc R . . . .
H14B H 0.098454 0.409304 0.728008 0.142 Uiso 1 1 calc R . . . .
C15 C 0.0756(2) 0.214(2) 0.691(2) 0.135(6) Uani 1 1 d D . . . .
H15A H 0.070244 0.245896 0.536282 0.162 Uiso 1 1 calc R . . . .
H15B H 0.075909 0.087674 0.698770 0.162 Uiso 1 1 calc R . . . .
C16 C 0.05974(19) 0.282(3) 0.866(3) 0.150(6) Uani 1 1 d D . . . .
H16A H 0.066152 0.263637 1.020216 0.180 Uiso 1 1 calc R . . . .
H16B H 0.058126 0.406663 0.844034 0.180 Uiso 1 1 calc R . . . .
C17 C 0.0372(2) 0.200(3) 0.854(4) 0.182(8) Uani 1 1 d D . . . .
H17A H 0.030931 0.214538 0.698400 0.219 Uiso 1 1 calc R . . . .
H17B H 0.038651 0.076580 0.883755 0.219 Uiso 1 1 calc R . . . .
C18 C 0.0220(3) 0.277(4) 1.022(5) 0.264(14) Uani 1 1 d D . . . .
H18A H 0.015808 0.382733 0.959659 0.396 Uiso 1 1 calc GR . . . .
H18B H 0.029967 0.302538 1.164942 0.396 Uiso 1 1 calc GR . . . .
H18C H 0.010469 0.196061 1.051281 0.396 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 C5 1.737(8) . ?
S1 C7 1.725(7) . ?
O2 C11 1.214(13) . ?
C1 C2 1.369(15) . ?
C1 C6 1.369(12) 7_556 ?
C1 C11 1.494(16) . ?
C2 H2 0.9300 . ?
C2 C3 1.394(13) . ?
C3 H3 0.9300 . ?
C3 C4 1.470(10) . ?
C4 C5 1.454(11) 7_556 ?
C4 C7 1.413(11) . ?
C5 C6 1.345(11) . ?
C6 H6 0.9300 . ?
C7 C7 1.372(12) 7_556 ?
C11 C12 1.483(16) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.475(13) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.530(13) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.524(14) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.521(14) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.509(16) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.493(17) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C7 S1 C5 91.2(3) . . ?
C2 C1 C6 119.6(10) . 7_556 ?
C2 C1 C11 119.3(9) . . ?
C6 C1 C11 121.2(10) 7_556 . ?
C1 C2 H2 117.7 . . ?
C1 C2 C3 124.5(9) . . ?
C3 C2 H2 117.7 . . ?
C2 C3 H3 122.4 . . ?
C2 C3 C4 115.2(7) . . ?
C4 C3 H3 122.4 . . ?
C5 C4 C3 118.5(7) 7_556 . ?
C7 C4 C3 133.3(7) . . ?
C7 C4 C5 108.2(7) . 7_556 ?
C4 C5 S1 112.5(6) 7_556 . ?
C6 C5 S1 127.3(7) . . ?
C6 C5 C4 120.2(8) . 7_556 ?
C1 C6 H6 119.0 7_556 . ?
C5 C6 C1 122.0(9) . 7_556 ?
C5 C6 H6 119.0 . . ?
C4 C7 S1 131.9(6) . . ?
C7 C7 S1 112.1(8) 7_556 . ?
C7 C7 C4 115.9(9) 7_556 . ?
O2 C11 C1 116.6(11) . . ?
O2 C11 C12 123.7(11) . . ?
C12 C11 C1 119.7(9) . . ?
C11 C12 H12A 108.5 . . ?
C11 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
C13 C12 C11 114.9(10) . . ?
C13 C12 H12A 108.5 . . ?
C13 C12 H12B 108.5 . . ?
C12 C13 H13A 109.3 . . ?
C12 C13 H13B 109.3 . . ?
C12 C13 C14 111.4(11) . . ?
H13A C13 H13B 108.0 . . ?
C14 C13 H13A 109.3 . . ?
C14 C13 H13B 109.3 . . ?
C13 C14 H14A 109.1 . . ?
C13 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
C15 C14 C13 112.6(11) . . ?
C15 C14 H14A 109.1 . . ?
C15 C14 H14B 109.1 . . ?
C14 C15 H15A 109.0 . . ?
C14 C15 H15B 109.0 . . ?
H15A C15 H15B 107.8 . . ?
C16 C15 C14 113.0(11) . . ?
C16 C15 H15A 109.0 . . ?
C16 C15 H15B 109.0 . . ?
C15 C16 H16A 108.5 . . ?
C15 C16 H16B 108.5 . . ?
H16A C16 H16B 107.5 . . ?
C17 C16 C15 115.1(13) . . ?
C17 C16 H16A 108.5 . . ?
C17 C16 H16B 108.5 . . ?
C16 C17 H17A 109.0 . . ?
C16 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C18 C17 C16 113.0(15) . . ?
C18 C17 H17A 109.0 . . ?
C18 C17 H17B 109.0 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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 C5 C6 C1 178.7(7) . . . 7_556 ?
O2 C11 C12 C13 8(2) . . . . ?
C1 C2 C3 C4 0.3(12) . . . . ?
C1 C11 C12 C13 -169.6(12) . . . . ?
C2 C1 C11 O2 176.7(10) . . . . ?
C2 C1 C11 C12 -5.9(17) . . . . ?
C2 C3 C4 C5 -0.7(9) . . . 7_556 ?
C2 C3 C4 C7 -179.7(7) . . . . ?
C3 C4 C7 S1 0.5(11) . . . . ?
C3 C4 C7 C7 178.6(7) . . . 7_556 ?
C4 C5 C6 C1 -1.2(12) 7_556 . . 7_556 ?
C5 S1 C7 C4 179.8(7) . . . . ?
C5 S1 C7 C7 1.6(7) . . . 7_556 ?
C5 C4 C7 S1 -178.6(6) 7_556 . . . ?
C5 C4 C7 C7 -0.4(10) 7_556 . . 7_556 ?
C6 C1 C2 C3 0.9(15) 7_556 . . . ?
C6 C1 C11 O2 -4.2(17) 7_556 . . . ?
C6 C1 C11 C12 173.1(11) 7_556 . . . ?
C7 S1 C5 C4 -1.4(6) . . . 7_556 ?
C7 S1 C5 C6 178.7(8) . . . . ?
C11 C1 C2 C3 -180.0(9) . . . . ?
C11 C12 C13 C14 -176.7(11) . . . . ?
C12 C13 C14 C15 -173.9(14) . . . . ?
C13 C14 C15 C16 -177.4(13) . . . . ?
C14 C15 C16 C17 -172.7(17) . . . . ?
C15 C16 C17 C18 -177.5(19) . . . . ?

_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_ro_344a_a
_database_code_depnum_ccdc_archive 'CCDC 1946323'
loop_
_audit_author_name
_audit_author_address
'Yunus Zorlu' 'Gebze Technical University'
_audit_update_record             
;
2019-08-09 deposited with the CCDC.	2020-07-31 downloaded from the CCDC.
;
_audit_creation_date             2018-12-19
_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         'C36 H36 N4 S2'
_chemical_formula_sum            'C36 H36 N4 S2'
_chemical_formula_weight         588.81
_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      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                   17.703(10)
_cell_length_b                   7.556(3)
_cell_length_c                   12.385(5)
_cell_angle_alpha                90
_cell_angle_beta                 106.60(3)
_cell_angle_gamma                90
_cell_volume                     1587.6(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1601
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      22.81
_cell_measurement_theta_min      2.40
_shelx_estimated_absorpt_T_max   0.984
_shelx_estimated_absorpt_T_min   0.952
_exptl_absorpt_coefficient_mu    0.199
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.232
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0913
_diffrn_reflns_av_unetI/netI     0.1648
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6702
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.013
_diffrn_reflns_theta_max         25.013
_diffrn_reflns_theta_min         2.951
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_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                   'microfocus sealed X-ray tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1287
_reflns_number_total             2755
_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       'APEX2 v2014.9-0 (Bruker AXS)'
_computing_data_collection       
'Bruker Instrument Service v2013.12.0.0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS)'
_computing_molecular_graphics    'MERCURY (Macrae et al., 2006)'
_computing_publication_material  
'MERCURY (Macrae et al., 2006), PLATON V1.16 (Spek, 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.747
_refine_diff_density_min         -0.552
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.964
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         2755
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.1855
_refine_ls_R_factor_gt           0.0805
_refine_ls_restrained_S_all      1.071
_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)+(0.1302P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1969
_refine_ls_wR_factor_ref         0.2513
_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. Restrained distances
 C12-C13
 1.55 with sigma of 0.02
 C13-C14
 1.55 with sigma of 0.02
 C14-C15
 1.55 with sigma of 0.02
 C15-C16
 1.9 with sigma of 0.02
 C16-C17
 1.55 with sigma of 0.02
 C17-C18
 1.55 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C13 \\sim C14: within 1.7A with sigma of 0.005 and sigma for terminal atoms of
0.08
C14 \\sim C15: within 1.7A with sigma of 0.005 and sigma for terminal atoms of
0.08
C15 \\sim C16: within 1.7A with sigma of 0.005 and sigma for terminal atoms of
0.08
C16 \\sim C17: within 1.7A with sigma of 0.005 and sigma for terminal atoms of
0.08
C17 \\sim C18: within 1.7A with sigma of 0.005 and sigma for terminal atoms of
0.08
4.a Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,
 H16B), C17(H17A,H17B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C6(H6)
4.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C)
;
_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 0.39828(9) 0.88080(16) 0.52208(12) 0.0418(5) Uani 1 1 d . . . . .
N1 N 0.6691(3) 0.9946(7) 0.1250(4) 0.0611(16) Uani 1 1 d . . . . .
N2 N 0.8136(4) 0.5516(7) 0.0922(5) 0.0735(18) Uani 1 1 d . . . . .
C1 C 0.6329(3) 0.6648(6) 0.3206(4) 0.0355(13) Uani 1 1 d . . . . .
C2 C 0.5666(4) 0.5709(7) 0.3302(4) 0.0424(15) Uani 1 1 d . . . . .
H2 H 0.5578 0.4569 0.3011 0.051 Uiso 1 1 calc R . . . .
C3 C 0.5146(3) 0.6427(6) 0.3811(4) 0.0385(14) Uani 1 1 d . . . . .
H3 H 0.4709 0.5782 0.3855 0.046 Uiso 1 1 calc R . . . .
C4 C 0.5273(3) 0.8124(6) 0.4262(4) 0.0337(13) Uani 1 1 d . . . . .
C5 C 0.5936(3) 0.9091(6) 0.4176(4) 0.0359(13) Uani 1 1 d . . . . .
C6 C 0.6476(3) 0.8359(7) 0.3671(4) 0.0385(14) Uani 1 1 d . . . . .
H6 H 0.6922 0.8986 0.3643 0.046 Uiso 1 1 calc R . . . .
C7 C 0.4840(3) 0.9174(6) 0.4833(4) 0.0376(14) Uani 1 1 d . . . . .
C8 C 0.6895(4) 0.8558(8) 0.1560(5) 0.0456(15) Uani 1 1 d . . . . .
C9 C 0.7716(4) 0.6055(7) 0.1379(5) 0.0511(16) Uani 1 1 d . . . . .
C10 C 0.7157(3) 0.6801(7) 0.1919(4) 0.0416(14) Uani 1 1 d . . . . .
C11 C 0.6883(3) 0.5857(7) 0.2643(4) 0.0395(14) Uani 1 1 d . . . . .
C12 C 0.7113(4) 0.3938(7) 0.2890(5) 0.0519(16) Uani 1 1 d D . . . .
H12A H 0.7406 0.3546 0.2382 0.062 Uiso 1 1 calc R . . . .
H12B H 0.6638 0.3226 0.2744 0.062 Uiso 1 1 calc R . . . .
C13 C 0.7616(4) 0.3624(9) 0.4113(6) 0.0788(19) Uani 1 1 d D U . . .
H13A H 0.7322 0.4021 0.4620 0.095 Uiso 1 1 calc R . . . .
H13B H 0.7706 0.2363 0.4230 0.095 Uiso 1 1 calc R . . . .
C14 C 0.8394(5) 0.4551(11) 0.4410(7) 0.109(2) Uani 1 1 d D U . . .
H14A H 0.8613 0.4427 0.3780 0.131 Uiso 1 1 calc R . . . .
H14B H 0.8300 0.5803 0.4491 0.131 Uiso 1 1 calc R . . . .
C15 C 0.8980(6) 0.3970(13) 0.5415(8) 0.140(3) Uani 1 1 d D U . . .
H15A H 0.9497 0.4229 0.5333 0.168 Uiso 1 1 calc R . . . .
H15B H 0.8939 0.2695 0.5473 0.168 Uiso 1 1 calc R . . . .
C16 C 0.8923(8) 0.4783(14) 0.6492(9) 0.155(3) Uani 1 1 d D U . . .
H16A H 0.8407 0.4469 0.6558 0.185 Uiso 1 1 calc R . . . .
H16B H 0.8917 0.6054 0.6379 0.185 Uiso 1 1 calc R . . . .
C17 C 0.9514(7) 0.4440(15) 0.7672(9) 0.154(3) Uani 1 1 d D U . . .
H17A H 0.9570 0.3183 0.7835 0.184 Uiso 1 1 calc R . . . .
H17B H 1.0029 0.4934 0.7719 0.184 Uiso 1 1 calc R . . . .
C18 C 0.9140(8) 0.5373(16) 0.8460(8) 0.173(5) Uani 1 1 d D U . . .
H18A H 0.9035 0.6582 0.8226 0.259 Uiso 1 1 calc GR . . . .
H18B H 0.9491 0.5340 0.9211 0.259 Uiso 1 1 calc GR . . . .
H18C H 0.8654 0.4794 0.8447 0.259 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 C5 1.742(5) 3_676 ?
S1 C7 1.740(5) . ?
N1 C8 1.140(6) . ?
N2 C9 1.131(7) . ?
C1 C2 1.406(8) . ?
C1 C6 1.409(7) . ?
C1 C11 1.481(7) . ?
C2 H2 0.9300 . ?
C2 C3 1.367(7) . ?
C3 H3 0.9300 . ?
C3 C4 1.391(6) . ?
C4 C5 1.412(7) . ?
C4 C7 1.424(7) . ?
C5 S1 1.742(5) 3_676 ?
C5 C6 1.397(7) . ?
C6 H6 0.9300 . ?
C7 C7 1.384(9) 3_676 ?
C8 C10 1.434(8) . ?
C9 C10 1.456(8) . ?
C10 C11 1.342(7) . ?
C11 C12 1.513(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.540(8) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.494(10) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C14 C15 1.443(10) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.498(12) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C16 C17 1.556(12) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.504(12) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 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
C7 S1 C5 90.1(2) . 3_676 ?
C2 C1 C6 119.3(5) . . ?
C2 C1 C11 121.1(4) . . ?
C6 C1 C11 119.6(5) . . ?
C1 C2 H2 119.1 . . ?
C3 C2 C1 121.8(5) . . ?
C3 C2 H2 119.1 . . ?
C2 C3 H3 120.1 . . ?
C2 C3 C4 119.9(5) . . ?
C4 C3 H3 120.1 . . ?
C3 C4 C5 119.3(5) . . ?
C3 C4 C7 131.7(5) . . ?
C5 C4 C7 109.0(4) . . ?
C4 C5 S1 114.1(4) . 3_676 ?
C6 C5 S1 124.7(4) . 3_676 ?
C6 C5 C4 121.2(5) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 C1 118.5(5) . . ?
C5 C6 H6 120.7 . . ?
C4 C7 S1 133.2(4) . . ?
C7 C7 S1 112.1(5) 3_676 . ?
C7 C7 C4 114.7(6) 3_676 . ?
N1 C8 C10 178.3(6) . . ?
N2 C9 C10 177.2(6) . . ?
C8 C10 C9 114.7(5) . . ?
C11 C10 C8 123.5(5) . . ?
C11 C10 C9 121.6(5) . . ?
C1 C11 C12 117.9(5) . . ?
C10 C11 C1 121.0(5) . . ?
C10 C11 C12 121.1(5) . . ?
C11 C12 H12A 109.0 . . ?
C11 C12 H12B 109.0 . . ?
C11 C12 C13 113.1(5) . . ?
H12A C12 H12B 107.8 . . ?
C13 C12 H12A 109.0 . . ?
C13 C12 H12B 109.0 . . ?
C12 C13 H13A 108.8 . . ?
C12 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 C12 113.8(6) . . ?
C14 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C13 C14 H14A 108.0 . . ?
C13 C14 H14B 108.0 . . ?
H14A C14 H14B 107.3 . . ?
C15 C14 C13 117.0(8) . . ?
C15 C14 H14A 108.0 . . ?
C15 C14 H14B 108.0 . . ?
C14 C15 H15A 108.4 . . ?
C14 C15 H15B 108.4 . . ?
C14 C15 C16 115.4(9) . . ?
H15A C15 H15B 107.5 . . ?
C16 C15 H15A 108.4 . . ?
C16 C15 H15B 108.4 . . ?
C15 C16 H16A 106.2 . . ?
C15 C16 H16B 106.2 . . ?
C15 C16 C17 124.7(10) . . ?
H16A C16 H16B 106.4 . . ?
C17 C16 H16A 106.2 . . ?
C17 C16 H16B 106.2 . . ?
C16 C17 H17A 111.1 . . ?
C16 C17 H17B 111.1 . . ?
H17A C17 H17B 109.1 . . ?
C18 C17 C16 103.2(9) . . ?
C18 C17 H17A 111.1 . . ?
C18 C17 H17B 111.1 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
