# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_arakawa-YI3-1(2nd)-FRE
_database_code_depnum_ccdc_archive 'CCDC 2079784'
loop_
_audit_author_name
_audit_author_address
'Yuki Arakawa'
;Toyohashi University of Technology
Japan
;
_audit_update_record             
;
2021-04-24 deposited with the CCDC.	2022-01-28 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C15 H11 N O2 S'
_chemical_formula_moiety         'C15 H11 N O2 S'
_chemical_formula_weight         269.32
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   6.728(3)
_cell_length_b                   9.172(5)
_cell_length_c                   10.765(6)
_cell_angle_alpha                106.416(14)
_cell_angle_beta                 91.946(13)
_cell_angle_gamma                91.011(10)
_cell_volume                     636.6(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2808
_cell_measurement_theta_min      1.97
_cell_measurement_theta_max      30.36
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.405
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             280.00
_exptl_absorpt_coefficient_mu    0.250
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_T_max  0.988

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      123
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Saturn724'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 14.222
_diffrn_reflns_number            10603
_diffrn_reflns_av_unetI/netI     0.0363
_diffrn_reflns_av_R_equivalents  0.0466
_diffrn_reflns_theta_max         27.444
_diffrn_reflns_theta_min         3.031
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2874
_reflns_number_gt                2705
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0551
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1275
_refine_ls_wR_factor_gt          0.1247
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2874
_refine_ls_number_parameters     173
_refine_ls_goodness_of_fit_ref   1.202
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0631P)²+0.2220P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.39
_refine_diff_density_min         -0.72
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 -0.25072(6) 0.17710(5) 0.30738(4) 0.02340(16) Uani 1 1 d . . . . .
O1 O 0.59629(18) 0.45470(14) 0.11660(12) 0.0243(3) Uani 1 1 d . . . . .
O2 O 0.54085(17) 0.22361(14) -0.03107(11) 0.0214(3) Uani 1 1 d . . . . .
N1 N 1.2566(3) 0.2169(2) -0.45633(16) 0.0341(4) Uani 1 1 d . . . . .
C1 C -0.3371(3) 0.3523(2) 0.41206(17) 0.0258(4) Uani 1 1 d . . . . .
H1A H -0.352733 0.426732 0.362885 0.031 Uiso 1 1 calc R U . . .
H1B H -0.240058 0.391978 0.484295 0.031 Uiso 1 1 calc R U . . .
H1C H -0.465461 0.333524 0.445956 0.031 Uiso 1 1 calc R U . . .
C2 C -0.0272(2) 0.23076(19) 0.25003(15) 0.0184(3) Uani 1 1 d . . . . .
C3 C 0.0546(2) 0.37827(19) 0.28524(15) 0.0194(3) Uani 1 1 d . . . . .
H3 H -0.008745 0.457227 0.346651 0.023 Uiso 1 1 calc R U . . .
C4 C 0.2290(2) 0.40993(19) 0.23051(15) 0.0188(3) Uani 1 1 d . . . . .
H4 H 0.285282 0.510182 0.255894 0.023 Uiso 1 1 calc R U . . .
C5 C 0.3216(2) 0.29525(19) 0.13851(15) 0.0174(3) Uani 1 1 d . . . . .
C6 C 0.2408(2) 0.14674(19) 0.10426(16) 0.0196(3) Uani 1 1 d . . . . .
H6 H 0.303787 0.067843 0.042600 0.024 Uiso 1 1 calc R U . . .
C7 C 0.0693(2) 0.11497(19) 0.16021(16) 0.0198(3) Uani 1 1 d . . . . .
H7 H 0.016224 0.013801 0.137614 0.024 Uiso 1 1 calc R U . . .
C8 C 0.5012(2) 0.33702(19) 0.07865(15) 0.0184(3) Uani 1 1 d . . . . .
C9 C 0.6942(2) 0.23588(19) -0.11224(15) 0.0181(3) Uani 1 1 d . . . . .
C10 C 0.8804(2) 0.30162(19) -0.06803(16) 0.0192(3) Uani 1 1 d . . . . .
H10 H 0.907973 0.349237 0.021581 0.023 Uiso 1 1 calc R U . . .
C11 C 1.0256(2) 0.29604(19) -0.15822(16) 0.0195(3) Uani 1 1 d . . . . .
H11 H 1.153753 0.340831 -0.130354 0.023 Uiso 1 1 calc R U . . .
C12 C 0.9833(3) 0.22455(19) -0.28997(16) 0.0203(4) Uani 1 1 d . . . . .
C13 C 0.7950(3) 0.1585(2) -0.33266(16) 0.0215(4) Uani 1 1 d . . . . .
H13 H 0.767023 0.109754 -0.422048 0.026 Uiso 1 1 calc R U . . .
C14 C 0.6497(3) 0.16483(19) -0.24313(16) 0.0207(3) Uani 1 1 d . . . . .
H14 H 0.520864 0.121176 -0.270702 0.025 Uiso 1 1 calc R U . . .
C15 C 1.1354(3) 0.2197(2) -0.38263(17) 0.0247(4) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       CrystalClear
_computing_data_reduction        CrystalClear
_computing_structure_solution    'SIR92 (Altomare, et al., 1994)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C2 1.7586(18) . ?
S1 C1 1.801(2) . ?
O1 C8 1.204(2) . ?
O2 C8 1.373(2) . ?
O2 C9 1.3975(19) . ?
N1 C15 1.152(2) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.395(2) . ?
C2 C7 1.404(2) . ?
C3 C4 1.392(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.397(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.401(2) . ?
C5 C8 1.482(2) . ?
C6 C7 1.383(2) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C9 C10 1.389(2) . ?
C9 C14 1.395(2) . ?
C10 C11 1.392(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.401(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.400(2) . ?
C12 C15 1.446(2) . ?
C13 C14 1.386(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?

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
C2 S1 C1 103.92(9) . . ?
C8 O2 C9 122.78(13) . . ?
S1 C1 H1A 109.5 . . ?
S1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
S1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 119.29(15) . . ?
C3 C2 S1 124.63(13) . . ?
C7 C2 S1 116.06(13) . . ?
C4 C3 C2 120.10(15) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 120.45(16) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 119.44(15) . . ?
C4 C5 C8 118.13(15) . . ?
C6 C5 C8 122.42(15) . . ?
C7 C6 C5 120.03(15) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C6 C7 C2 120.65(16) . . ?
C6 C7 H7 119.7 . . ?
C2 C7 H7 119.7 . . ?
O1 C8 O2 124.03(15) . . ?
O1 C8 C5 125.86(15) . . ?
O2 C8 C5 110.07(14) . . ?
C10 C9 C14 122.06(15) . . ?
C10 C9 O2 123.98(15) . . ?
C14 C9 O2 113.77(15) . . ?
C9 C10 C11 118.39(15) . . ?
C9 C10 H10 120.8 . . ?
C11 C10 H10 120.8 . . ?
C10 C11 C12 120.20(16) . . ?
C10 C11 H11 119.9 . . ?
C12 C11 H11 119.9 . . ?
C13 C12 C11 120.61(15) . . ?
C13 C12 C15 119.78(16) . . ?
C11 C12 C15 119.62(16) . . ?
C14 C13 C12 119.30(15) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
C13 C14 C9 119.44(16) . . ?
C13 C14 H14 120.3 . . ?
C9 C14 H14 120.3 . . ?
N1 C15 C12 179.5(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C1 S1 C2 C3 1.06(17) . . . . ?
C1 S1 C2 C7 -177.30(12) . . . . ?
C7 C2 C3 C4 0.7(2) . . . . ?
S1 C2 C3 C4 -177.64(12) . . . . ?
C2 C3 C4 C5 1.1(2) . . . . ?
C3 C4 C5 C6 -1.8(2) . . . . ?
C3 C4 C5 C8 176.99(14) . . . . ?
C4 C5 C6 C7 0.8(2) . . . . ?
C8 C5 C6 C7 -177.94(15) . . . . ?
C5 C6 C7 C2 1.0(3) . . . . ?
C3 C2 C7 C6 -1.7(2) . . . . ?
S1 C2 C7 C6 176.77(13) . . . . ?
C9 O2 C8 O1 -1.8(2) . . . . ?
C9 O2 C8 C5 175.84(13) . . . . ?
C4 C5 C8 O1 13.5(3) . . . . ?
C6 C5 C8 O1 -167.71(17) . . . . ?
C4 C5 C8 O2 -164.09(14) . . . . ?
C6 C5 C8 O2 14.7(2) . . . . ?
C8 O2 C9 C10 39.6(2) . . . . ?
C8 O2 C9 C14 -145.26(15) . . . . ?
C14 C9 C10 C11 0.2(2) . . . . ?
O2 C9 C10 C11 174.95(14) . . . . ?
C9 C10 C11 C12 -0.4(2) . . . . ?
C10 C11 C12 C13 0.2(2) . . . . ?
C10 C11 C12 C15 179.93(15) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C15 C12 C13 C14 -179.47(16) . . . . ?
C12 C13 C14 C9 -0.5(3) . . . . ?
C10 C9 C14 C13 0.3(3) . . . . ?
O2 C9 C14 C13 -174.99(15) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        '4-cyanophenyl 4-(methylthio)benzoate'
####################################################################### 
# 
# 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_c1-hy-fre
_database_code_depnum_ccdc_archive 'CCDC 2079786'
loop_
_audit_author_name
_audit_author_address
'Yuki Arakawa'
;Toyohashi University of Technology
Japan
;
_audit_update_record             
;
2021-04-24 deposited with the CCDC.	2022-01-28 downloaded from the CCDC.
;
_audit_creation_date             2018-11-17
_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        '1,4-phenylene bis(4-(methylthio)benzoate)'
_chemical_formula_moiety         '2(C22 H18 O4 S2)'
_chemical_formula_sum            'C44 H36 O8 S4'
_chemical_formula_weight         820.97
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C44 H36 Cl4 O8 '
_chemical_oxdiff_usercomment     HyPix
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           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                   22.6272(12)
_cell_length_b                   5.4014(3)
_cell_length_c                   7.6641(4)
_cell_angle_alpha                90
_cell_angle_beta                 95.178(5)
_cell_angle_gamma                90
_cell_volume                     932.87(9)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3495
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.4730
_cell_measurement_theta_min      2.6780
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.313
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.461
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             428
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.02
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0230
_diffrn_reflns_av_unetI/netI     0.0276
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.869
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            6278
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.869
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.631
_diffrn_reflns_theta_min         2.712
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.869
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -105.00  62.00   0.50    4.72    --  -15.80  45.00   0.00  334
  2  ω    -34.00  49.00   0.50    4.72    --  -15.80  45.00  60.00  166
  3  ω    -92.00 -66.00   0.50    4.72    --  -15.80  45.00 150.00   52
  4  ω     15.00  40.00   0.50    4.72    --  -15.80  45.00 150.00   50
  5  ω    -97.00 -38.00   0.50    4.72    --  -15.80  45.00 120.00  118
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC HyPix-6000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0098170000
_diffrn_orient_matrix_UB_12      -0.1026624000
_diffrn_orient_matrix_UB_13      0.0474120000
_diffrn_orient_matrix_UB_21      -0.0298974000
_diffrn_orient_matrix_UB_22      0.0310703000
_diffrn_orient_matrix_UB_23      -0.0270316000
_diffrn_orient_matrix_UB_31      0.0010426000
_diffrn_orient_matrix_UB_32      -0.0758756000
_diffrn_orient_matrix_UB_33      -0.0751221000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              FR-E+
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1901
_reflns_number_total             2081
_reflns_odcompleteness_completeness 99.85
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.49
_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       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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         0.376
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     128
_refine_ls_number_reflns         2081
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0314
_refine_ls_restrained_S_all      1.065
_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)+(0.0335P)²+0.5887P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0817
_refine_ls_wR_factor_ref         0.0835
_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:
 C7(H7), C14(H14), C6(H6), C10(H10), C9(H9), C13(H13)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C)
;
_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 0.09290(2) 0.38569(7) 0.12453(5) 0.02083(12) Uani 1 1 d . . . . .
O2 O 0.38234(4) 0.44025(18) 0.37760(12) 0.0170(2) Uani 1 1 d . . . . .
O3 O 0.35530(5) 0.7825(2) 0.51691(17) 0.0371(3) Uani 1 1 d . . . . .
C7 C 0.26762(6) 0.3344(3) 0.25321(17) 0.0170(3) Uani 1 1 d . . . . .
H7 H 0.297384 0.222936 0.231360 0.020 Uiso 1 1 calc R . . . .
C14 C 0.47291(6) 0.6793(3) 0.38777(17) 0.0167(3) Uani 1 1 d . . . . .
H14 H 0.454490 0.797198 0.312931 0.020 Uiso 1 1 calc R . . . .
C6 C 0.20952(6) 0.2895(3) 0.18799(18) 0.0174(3) Uani 1 1 d . . . . .
H6 H 0.200340 0.147445 0.122536 0.021 Uiso 1 1 calc R . . . .
C10 C 0.17834(6) 0.6673(3) 0.31937(17) 0.0174(3) Uani 1 1 d . . . . .
H10 H 0.148613 0.778610 0.342025 0.021 Uiso 1 1 calc R . . . .
C9 C 0.23669(6) 0.7107(3) 0.38458(18) 0.0170(3) Uani 1 1 d . . . . .
H9 H 0.245877 0.851680 0.451282 0.020 Uiso 1 1 calc R . . . .
C12 C 0.44189(5) 0.4776(3) 0.44155(17) 0.0151(3) Uani 1 1 d . . . . .
C5 C 0.16472(5) 0.4563(3) 0.22000(17) 0.0156(3) Uani 1 1 d . . . . .
C8 C 0.28137(5) 0.5467(3) 0.35149(17) 0.0153(3) Uani 1 1 d . . . . .
C13 C 0.46753(6) 0.2983(3) 0.55156(17) 0.0164(3) Uani 1 1 d . . . . .
H13 H 0.445331 0.164150 0.584765 0.020 Uiso 1 1 calc R . . . .
C11 C 0.34257(6) 0.6079(3) 0.42505(18) 0.0182(3) Uani 1 1 d . . . . .
C4 C 0.04812(6) 0.6185(3) 0.2143(2) 0.0260(3) Uani 1 1 d . . . . .
H4A H 0.007473 0.596887 0.169247 0.039 Uiso 1 1 calc GR . . . .
H4B H 0.061579 0.779309 0.182230 0.039 Uiso 1 1 calc GR . . . .
H4C H 0.051311 0.603970 0.339675 0.039 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 1.7628(13) . ?
S1 C4 1.7908(16) . ?
O2 C12 1.4063(14) . ?
O2 C11 1.3495(16) . ?
O3 C11 1.1964(18) . ?
C7 C6 1.3851(18) . ?
C7 C8 1.3915(19) . ?
C14 C12 1.3790(19) . ?
C14 C13 1.3908(18) 3_666 ?
C6 C5 1.3942(19) . ?
C10 C9 1.3889(18) . ?
C10 C5 1.3900(19) . ?
C9 C8 1.3848(18) . ?
C12 C13 1.3775(19) . ?
C8 C11 1.4844(17) . ?

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
C5 S1 C4 102.76(7) . . ?
C11 O2 C12 116.81(10) . . ?
C6 C7 C8 119.89(12) . . ?
C12 C14 C13 118.22(12) . 3_666 ?
C7 C6 C5 120.31(13) . . ?
C9 C10 C5 119.48(12) . . ?
C8 C9 C10 120.81(13) . . ?
C14 C12 O2 120.45(12) . . ?
C13 C12 O2 116.73(12) . . ?
C13 C12 C14 122.75(12) . . ?
C6 C5 S1 116.41(10) . . ?
C10 C5 S1 123.74(10) . . ?
C10 C5 C6 119.84(12) . . ?
C7 C8 C11 122.99(12) . . ?
C9 C8 C7 119.67(12) . . ?
C9 C8 C11 117.34(12) . . ?
C12 C13 C14 119.03(13) . 3_666 ?
O2 C11 C8 111.72(11) . . ?
O3 C11 O2 123.81(12) . . ?
O3 C11 C8 124.47(13) . . ?

_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 1.792
_oxdiff_exptl_absorpt_empirical_full_min 0.719
####################################################################### 
# 
# 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_1scb-2
_database_code_depnum_ccdc_archive 'CCDC 2098139'
loop_
_audit_author_name
_audit_author_address
'Yuki Arakawa'
;Toyohashi University of Technology
Japan
;
_audit_update_record             
;
2021-07-21 deposited with the CCDC.	2022-01-28 downloaded from the CCDC.
;
_audit_creation_date             2021-07-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            1SCB
_chemical_name_systematic        ?
_chemical_formula_moiety         'C14 H11 N S'
_chemical_formula_sum            'C14 H11 N S'
_chemical_formula_weight         225.30
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C14H11NS
_chemical_oxdiff_usercomment     '120 K'
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           7
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   9.3222(3)
_cell_length_b                   13.9997(5)
_cell_length_c                   13.3672(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.663(4)
_cell_angle_gamma                90
_cell_volume                     1719.78(11)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    11540
_cell_measurement_temperature    120
_cell_measurement_theta_max      29.9540
_cell_measurement_theta_min      2.7980
_shelx_estimated_absorpt_T_max   0.975
_shelx_estimated_absorpt_T_min   0.963
_exptl_absorpt_coefficient_mu    0.251
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84905
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             708
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.895
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            28710
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.799
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.048
_diffrn_reflns_theta_min         2.122
_diffrn_ambient_temperature      120
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.895
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -16.00   9.00   0.50    3.53    --    5.00  45.00  60.00   50
  2  ω    -53.00 -27.00   0.50    3.53    --    5.00  45.00 150.00   52
  3  ω     59.00  90.00   0.50    3.53    --    5.00  45.00  60.00   62
  4  ω    -20.00   6.00   0.50    3.53    --  -10.20  45.00  90.00   52
  5  ω    -92.00 -57.00   0.50    3.53    --  -10.20  45.00  90.00   70
  6  ω     32.00  74.00   0.50    3.53    --  -10.20  45.00  90.00   84
  7  ω    -97.00  78.00   0.50    3.53    --  -10.20  45.00 150.00  350
  8  ω    -86.00  75.00   0.50    3.53    --  -10.20  45.00   0.00  322
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC HyPix-6000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0373652000
_diffrn_orient_matrix_UB_12      -0.0373176000
_diffrn_orient_matrix_UB_13      0.0207697000
_diffrn_orient_matrix_UB_21      0.0466463000
_diffrn_orient_matrix_UB_22      -0.0340360000
_diffrn_orient_matrix_UB_23      -0.0172461000
_diffrn_orient_matrix_UB_31      0.0487710000
_diffrn_orient_matrix_UB_32      0.0039890000
_diffrn_orient_matrix_UB_33      0.0465864000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              FR-E+
_reflns_Friedel_coverage         0.780
_reflns_Friedel_fraction_full    0.937
_reflns_Friedel_fraction_max     0.701
_reflns_number_gt                7504
_reflns_number_total             8798
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.42
_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       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_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         0.557
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.057
_refine_ls_abs_structure_details 
;
 Flack x determined using 2954 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.18(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.916
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         8798
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0439
_refine_ls_restrained_S_all      0.916
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1201
_refine_ls_wR_factor_ref         0.1276
_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), C9(H9), C11(H11), C12(H12), C30(H30),
 C31(H31), C33(H33), C34(H34), C36(H36), C37(H37), C39(H39), C40(H40), C16(H16),
  C17(H17), C19(H19), C20(H20), C22(H22), C23(H23), C25(H25), C26(H26)
2.b Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C42(H42A,H42B,H42C), C28(H28A,H28B,H28C)
;
_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 0.38225(7) 0.43074(5) 0.27636(6) 0.02528(18) Uani 1 1 d . . . . .
N1 N 1.1720(4) 0.4376(3) 1.0289(3) 0.0452(8) Uani 1 1 d . . . . .
C1 C 0.5056(3) 0.42456(19) 0.3910(2) 0.0206(6) Uani 1 1 d . . . . .
C2 C 0.5018(3) 0.4994(2) 0.4595(2) 0.0255(6) Uani 1 1 d . . . . .
H2 H 0.431516 0.548612 0.443675 0.031 Uiso 1 1 calc R . . . .
C3 C 0.5980(3) 0.5032(2) 0.5496(2) 0.0248(6) Uani 1 1 d . . . . .
H3 H 0.592746 0.554879 0.594922 0.030 Uiso 1 1 calc R . . . .
C4 C 0.7031(4) 0.43257(19) 0.5757(2) 0.0220(6) Uani 1 1 d . . . . .
C5 C 0.7074(3) 0.3576(2) 0.5072(2) 0.0270(6) Uani 1 1 d . . . . .
H5 H 0.778455 0.308873 0.522918 0.032 Uiso 1 1 calc R . . . .
C6 C 0.6093(3) 0.3530(2) 0.4161(2) 0.0278(6) Uani 1 1 d . . . . .
H6 H 0.613339 0.300967 0.371112 0.033 Uiso 1 1 calc R . . . .
C7 C 0.8067(3) 0.43590(19) 0.6717(3) 0.0216(6) Uani 1 1 d . . . . .
C8 C 0.7630(3) 0.4681(2) 0.7605(2) 0.0289(6) Uani 1 1 d . . . . .
H8 H 0.666235 0.490559 0.757726 0.035 Uiso 1 1 calc R . . . .
C9 C 0.8557(3) 0.4684(2) 0.8519(2) 0.0314(7) Uani 1 1 d . . . . .
H9 H 0.822652 0.489729 0.911599 0.038 Uiso 1 1 calc R . . . .
C10 C 0.9979(4) 0.4374(2) 0.8564(3) 0.0263(7) Uani 1 1 d . . . . .
C11 C 1.0464(3) 0.4072(2) 0.7690(3) 0.0268(6) Uani 1 1 d . . . . .
H11 H 1.144215 0.386911 0.771908 0.032 Uiso 1 1 calc R . . . .
C12 C 0.9518(3) 0.4068(2) 0.6782(2) 0.0257(6) Uani 1 1 d . . . . .
H12 H 0.985665 0.386396 0.618498 0.031 Uiso 1 1 calc R . . . .
C13 C 1.0950(4) 0.4375(2) 0.9520(3) 0.0316(8) Uani 1 1 d . . . . .
C14 C 0.4049(4) 0.3179(2) 0.2167(3) 0.0337(7) Uani 1 1 d . . . . .
H14A H 0.338305 0.314303 0.151785 0.051 Uiso 1 1 calc GR . . . .
H14B H 0.383192 0.265892 0.261011 0.051 Uiso 1 1 calc GR . . . .
H14C H 0.505416 0.311845 0.204919 0.051 Uiso 1 1 calc GR . . . .
S3 S -0.17187(8) 0.23007(6) 0.21296(7) 0.0341(2) Uani 1 1 d . . . . .
N3 N 0.5658(4) 0.2481(2) 0.9919(3) 0.0466(8) Uani 1 1 d . . . . .
C29 C -0.0522(3) 0.2385(2) 0.3290(2) 0.0266(6) Uani 1 1 d . . . . .
C30 C -0.0724(4) 0.1752(2) 0.4043(2) 0.0337(7) Uani 1 1 d . . . . .
H30 H -0.148639 0.129523 0.391583 0.040 Uiso 1 1 calc R . . . .
C31 C 0.0170(3) 0.1772(2) 0.4986(2) 0.0304(6) Uani 1 1 d . . . . .
H31 H 0.000402 0.133069 0.549387 0.036 Uiso 1 1 calc R . . . .
C32 C 0.1302(3) 0.2425(2) 0.5201(3) 0.0243(6) Uani 1 1 d . . . . .
C33 C 0.1511(3) 0.3052(2) 0.4434(2) 0.0304(6) Uani 1 1 d . . . . .
H33 H 0.228660 0.349948 0.455829 0.036 Uiso 1 1 calc R . . . .
C34 C 0.0621(3) 0.3044(2) 0.3491(3) 0.0312(7) Uani 1 1 d . . . . .
H34 H 0.078739 0.348548 0.298260 0.037 Uiso 1 1 calc R . . . .
C35 C 0.2268(3) 0.2440(2) 0.6217(2) 0.0239(6) Uani 1 1 d . . . . .
C36 C 0.2073(3) 0.1783(2) 0.6962(3) 0.0342(7) Uani 1 1 d . . . . .
H36 H 0.133032 0.131447 0.681457 0.041 Uiso 1 1 calc R . . . .
C37 C 0.2937(4) 0.1793(2) 0.7916(3) 0.0356(7) Uani 1 1 d . . . . .
H37 H 0.279506 0.133866 0.841780 0.043 Uiso 1 1 calc R . . . .
C38 C 0.4046(3) 0.2506(2) 0.8122(2) 0.0275(7) Uani 1 1 d . . . . .
C39 C 0.4244(3) 0.3132(2) 0.7404(3) 0.0308(6) Uani 1 1 d . . . . .
H39 H 0.500233 0.359112 0.754012 0.037 Uiso 1 1 calc R . . . .
C40 C 0.3361(3) 0.3120(2) 0.6467(3) 0.0299(6) Uani 1 1 d . . . . .
H40 H 0.350160 0.358745 0.597817 0.036 Uiso 1 1 calc R . . . .
C41 C 0.4934(4) 0.2483(2) 0.9124(3) 0.0335(7) Uani 1 1 d . . . . .
C42 C -0.0915(4) 0.3052(3) 0.1291(3) 0.0399(8) Uani 1 1 d . . . . .
H42A H -0.152122 0.304533 0.061687 0.060 Uiso 1 1 calc GR . . . .
H42B H 0.005972 0.281496 0.124211 0.060 Uiso 1 1 calc GR . . . .
H42C H -0.084477 0.370613 0.155517 0.060 Uiso 1 1 calc GR . . . .
S2 S 0.84928(7) 0.06481(6) 0.73178(6) 0.02785(19) Uani 1 1 d . . . . .
N2 N 0.0827(4) 0.0837(3) -0.0291(3) 0.0449(8) Uani 1 1 d . . . . .
C15 C 0.7213(4) 0.0695(2) 0.6187(3) 0.0257(7) Uani 1 1 d . . . . .
C16 C 0.7368(3) 0.0014(2) 0.5445(2) 0.0258(6) Uani 1 1 d . . . . .
H16 H 0.812904 -0.044388 0.556871 0.031 Uiso 1 1 calc R . . . .
C17 C 0.6411(3) 0.0009(2) 0.4530(2) 0.0255(6) Uani 1 1 d . . . . .
H17 H 0.652806 -0.045046 0.402690 0.031 Uiso 1 1 calc R . . . .
C18 C 0.5274(3) 0.06744(19) 0.4339(3) 0.0212(6) Uani 1 1 d . . . . .
C19 C 0.5132(3) 0.1329(2) 0.5088(2) 0.0251(6) Uani 1 1 d . . . . .
H19 H 0.435681 0.177721 0.497400 0.030 Uiso 1 1 calc R . . . .
C20 C 0.6082(3) 0.1352(2) 0.5997(2) 0.0255(6) Uani 1 1 d . . . . .
H20 H 0.596397 0.181685 0.649442 0.031 Uiso 1 1 calc R . . . .
C21 C 0.4299(4) 0.06979(19) 0.3350(3) 0.0228(6) Uani 1 1 d . . . . .
C22 C 0.4879(3) 0.0612(2) 0.2445(2) 0.0256(6) Uani 1 1 d . . . . .
H22 H 0.589586 0.052202 0.248079 0.031 Uiso 1 1 calc R . . . .
C23 C 0.4002(3) 0.0657(2) 0.1518(2) 0.0282(6) Uani 1 1 d . . . . .
H23 H 0.441351 0.060688 0.091596 0.034 Uiso 1 1 calc R . . . .
C24 C 0.2494(3) 0.0775(2) 0.1454(3) 0.0241(6) Uani 1 1 d . . . . .
C25 C 0.1900(3) 0.0859(2) 0.2346(3) 0.0252(6) Uani 1 1 d . . . . .
H25 H 0.088003 0.093799 0.231049 0.030 Uiso 1 1 calc R . . . .
C26 C 0.2799(3) 0.08268(19) 0.3272(2) 0.0235(6) Uani 1 1 d . . . . .
H26 H 0.239033 0.089370 0.387344 0.028 Uiso 1 1 calc R . . . .
C27 C 0.1567(4) 0.0815(2) 0.0485(3) 0.0314(7) Uani 1 1 d . . . . .
C28 C 0.8262(4) 0.1778(2) 0.7892(3) 0.0370(7) Uani 1 1 d . . . . .
H28A H 0.841139 0.229111 0.742250 0.055 Uiso 1 1 calc GR . . . .
H28B H 0.897154 0.184010 0.851855 0.055 Uiso 1 1 calc GR . . . .
H28C H 0.727483 0.182091 0.805119 0.055 Uiso 1 1 calc GR . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.756(3) . ?
S1 C14 1.798(3) . ?
N1 C13 1.150(5) . ?
C1 C2 1.396(4) . ?
C1 C6 1.393(4) . ?
C2 C3 1.377(4) . ?
C3 C4 1.394(4) . ?
C4 C5 1.397(4) . ?
C4 C7 1.472(5) . ?
C5 C6 1.396(4) . ?
C7 C8 1.393(4) . ?
C7 C12 1.402(4) . ?
C8 C9 1.373(4) . ?
C9 C10 1.386(4) . ?
C10 C11 1.388(5) . ?
C10 C13 1.437(5) . ?
C11 C12 1.375(5) . ?
S3 C29 1.756(3) . ?
S3 C42 1.790(3) . ?
N3 C41 1.159(5) . ?
C29 C30 1.377(4) . ?
C29 C34 1.402(4) . ?
C30 C31 1.390(4) . ?
C31 C32 1.389(4) . ?
C32 C33 1.388(4) . ?
C32 C35 1.499(5) . ?
C33 C34 1.388(5) . ?
C35 C36 1.390(4) . ?
C35 C40 1.393(4) . ?
C36 C37 1.390(5) . ?
C37 C38 1.430(4) . ?
C38 C39 1.336(5) . ?
C38 C41 1.452(5) . ?
C39 C40 1.379(4) . ?
S2 C15 1.763(4) . ?
S2 C28 1.787(4) . ?
N2 C27 1.145(5) . ?
C15 C16 1.400(5) . ?
C15 C20 1.390(4) . ?
C16 C17 1.388(4) . ?
C17 C18 1.402(4) . ?
C18 C19 1.380(4) . ?
C18 C21 1.474(5) . ?
C19 C20 1.379(4) . ?
C21 C22 1.410(4) . ?
C21 C26 1.397(4) . ?
C22 C23 1.367(4) . ?
C23 C24 1.404(4) . ?
C24 C25 1.401(4) . ?
C24 C27 1.433(5) . ?
C25 C26 1.375(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 S1 C14 103.59(14) . . ?
C2 C1 S1 116.8(2) . . ?
C6 C1 S1 124.9(2) . . ?
C6 C1 C2 118.3(3) . . ?
C3 C2 C1 121.2(3) . . ?
C2 C3 C4 121.2(3) . . ?
C3 C4 C5 117.7(3) . . ?
C3 C4 C7 121.7(3) . . ?
C5 C4 C7 120.6(3) . . ?
C6 C5 C4 121.3(3) . . ?
C1 C6 C5 120.2(3) . . ?
C8 C7 C4 120.7(3) . . ?
C8 C7 C12 117.3(3) . . ?
C12 C7 C4 122.0(3) . . ?
C9 C8 C7 121.9(3) . . ?
C8 C9 C10 119.5(3) . . ?
C9 C10 C11 120.2(3) . . ?
C9 C10 C13 119.6(3) . . ?
C11 C10 C13 120.2(3) . . ?
C12 C11 C10 119.6(3) . . ?
C11 C12 C7 121.5(3) . . ?
N1 C13 C10 179.5(4) . . ?
C29 S3 C42 104.08(15) . . ?
C30 C29 S3 117.2(2) . . ?
C30 C29 C34 118.4(3) . . ?
C34 C29 S3 124.3(3) . . ?
C29 C30 C31 121.0(3) . . ?
C32 C31 C30 121.3(3) . . ?
C31 C32 C35 121.1(3) . . ?
C33 C32 C31 117.3(3) . . ?
C33 C32 C35 121.5(3) . . ?
C34 C33 C32 122.0(3) . . ?
C33 C34 C29 119.9(3) . . ?
C36 C35 C32 120.6(3) . . ?
C36 C35 C40 117.3(3) . . ?
C40 C35 C32 122.1(3) . . ?
C37 C36 C35 121.7(3) . . ?
C36 C37 C38 118.2(3) . . ?
C37 C38 C41 116.4(3) . . ?
C39 C38 C37 120.1(3) . . ?
C39 C38 C41 123.5(3) . . ?
C38 C39 C40 120.7(3) . . ?
C39 C40 C35 121.9(3) . . ?
N3 C41 C38 178.6(4) . . ?
C15 S2 C28 102.86(15) . . ?
C16 C15 S2 116.5(2) . . ?
C20 C15 S2 124.4(3) . . ?
C20 C15 C16 119.1(3) . . ?
C17 C16 C15 120.0(3) . . ?
C16 C17 C18 120.7(3) . . ?
C17 C18 C21 120.8(3) . . ?
C19 C18 C17 118.1(3) . . ?
C19 C18 C21 121.1(3) . . ?
C20 C19 C18 121.9(3) . . ?
C19 C20 C15 120.1(3) . . ?
C22 C21 C18 120.0(3) . . ?
C26 C21 C18 121.9(3) . . ?
C26 C21 C22 118.0(3) . . ?
C23 C22 C21 121.2(3) . . ?
C22 C23 C24 120.0(3) . . ?
C23 C24 C27 120.4(3) . . ?
C25 C24 C23 119.6(3) . . ?
C25 C24 C27 120.1(3) . . ?
C26 C25 C24 119.7(3) . . ?
C25 C26 C21 121.6(3) . . ?
N2 C27 C24 179.2(4) . . ?

_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 1.151
_oxdiff_exptl_absorpt_empirical_full_min 0.888
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
