# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_220418nishimotopy
_database_code_depnum_ccdc_archive 'CCDC 2234243'
loop_
_audit_author_name
_audit_author_address
'Hiroshi Nishimoto'
;University of Hyogo
Japan
;
_audit_update_record             
;
2023-01-04 deposited with the CCDC.	2023-07-27 downloaded from the CCDC.
;
_audit_creation_date             2022-04-19
_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            2Py-TP-BT
_chemical_name_systematic        
5-(2-pyridyl)-2-(thiopyran-4-ylidene)-1,3-benzodithiole
_chemical_formula_moiety         'C17 H11 N S3'
_chemical_formula_sum            'C17 H11 N S3'
_chemical_formula_weight         325.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         C17H11S3N1
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                   16.0602(12)
_cell_length_b                   7.6455(9)
_cell_length_c                   11.9152(13)
_cell_angle_alpha                90
_cell_angle_beta                 94.692(8)
_cell_angle_gamma                90
_cell_volume                     1458.1(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2655
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.9130
_cell_measurement_theta_min      2.5780
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.825
_exptl_absorpt_coefficient_mu    0.499
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70630
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.60a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'orangish yellow'
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.482
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_av_unetI/netI     0.0573
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.965
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            14545
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.965
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.341
_diffrn_reflns_theta_min         2.545
_diffrn_ambient_temperature      298
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.965
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     43.00  69.00   0.50   25.62    --   20.00  54.00   0.00   52
  2  ω    -42.00  94.00   0.50   25.62    --   20.00  54.00-120.00  272
  3  ω     11.00  84.00   0.50   25.62    --   20.00  54.00-150.00  146
  4  ω    -72.00  67.00   0.50   25.62    --   20.00  54.00 150.00  278
  5  ω    -73.00   5.00   0.50   25.62    --   20.00  54.00  30.00  156
  6  ω     62.00  87.00   0.50   25.62    --   20.00  54.00  30.00   50
  7  ω    -16.00  84.00   0.50   25.62    --   20.00  54.00-180.00  200
  8  ω    -29.00  -4.00   0.50   25.62    --   20.00  54.00   0.00   50
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0338832000
_diffrn_orient_matrix_UB_12      0.0441128000
_diffrn_orient_matrix_UB_13      -0.0295490000
_diffrn_orient_matrix_UB_21      -0.0258418000
_diffrn_orient_matrix_UB_22      -0.0210013000
_diffrn_orient_matrix_UB_23      0.0436042000
_diffrn_orient_matrix_UB_31      0.0120574000
_diffrn_orient_matrix_UB_32      0.0789489000
_diffrn_orient_matrix_UB_33      0.0281342000
_diffrn_oxdiff_digest_frames     
;
01f2a4ffc603345e1dc71d7265b6d8eeeb000256ec9
;
_diffrn_oxdiff_digest_hkl        
;
0108e3f24f2a2b1307043c255d93c2b2a5bc37
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2758
_reflns_number_total             4229
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.40.60a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.60a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.60a (Rigaku OD, 2019)'
_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         0.277
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       0.0015(8)
_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   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         4229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0887
_refine_ls_R_factor_gt           0.0465
_refine_ls_restrained_S_all      1.017
_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)+(0.0468P)²+0.2785P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1120
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C12(H12), C11(H11), C4(H4), C2(H2), C5(H5), C1(H1), C14(H14),
 C15(H15), C17(H17), C16(H16)
;
_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
S3 S 0.54841(3) 0.77331(7) 0.52841(4) 0.03373(15) Uani 1 1 d . . . . .
S2 S 0.50201(3) 0.54984(8) 0.71775(5) 0.03616(15) Uani 1 1 d . . . . .
S1 S 0.19327(3) 0.70527(11) 0.47041(6) 0.0597(2) Uani 1 1 d . . . . .
N1 N 0.90520(11) 0.8079(3) 0.79823(16) 0.0462(5) Uani 1 1 d . . . . .
C7 C 0.60719(11) 0.6126(3) 0.72017(16) 0.0287(4) Uani 1 1 d . . . . .
C8 C 0.62930(11) 0.7138(3) 0.62875(16) 0.0284(4) Uani 1 1 d . . . . .
C6 C 0.46824(12) 0.6632(3) 0.59297(16) 0.0288(4) Uani 1 1 d . . . . .
C3 C 0.38663(12) 0.6629(3) 0.54989(17) 0.0300(4) Uani 1 1 d . . . . .
C9 C 0.71226(12) 0.7636(3) 0.62141(17) 0.0317(4) Uani 1 1 d . . . . .
H9 H 0.727014 0.828717 0.560164 0.038 Uiso 1 1 calc R . . . .
C12 C 0.66795(12) 0.5628(3) 0.80405(16) 0.0333(5) Uani 1 1 d . . . . .
H12 H 0.653719 0.494398 0.864111 0.040 Uiso 1 1 calc R . . . .
C10 C 0.77319(11) 0.7153(3) 0.70640(17) 0.0322(5) Uani 1 1 d . . . . .
C11 C 0.74999(12) 0.6163(3) 0.79727(17) 0.0353(5) Uani 1 1 d . . . . .
H11 H 0.790295 0.585566 0.854363 0.042 Uiso 1 1 calc R . . . .
C4 C 0.36009(13) 0.7538(3) 0.44561(18) 0.0347(5) Uani 1 1 d . . . . .
H4 H 0.401385 0.799624 0.403795 0.042 Uiso 1 1 calc R . . . .
C13 C 0.86234(12) 0.7690(3) 0.69968(18) 0.0352(5) Uani 1 1 d . . . . .
C2 C 0.32290(12) 0.5673(3) 0.60651(18) 0.0376(5) Uani 1 1 d . . . . .
H2 H 0.340884 0.494274 0.666055 0.045 Uiso 1 1 calc R . . . .
C5 C 0.28073(13) 0.7760(3) 0.40593(19) 0.0412(5) Uani 1 1 d . . . . .
H5 H 0.271232 0.834538 0.337661 0.049 Uiso 1 1 calc R . . . .
C1 C 0.24056(13) 0.5779(3) 0.57843(19) 0.0452(6) Uani 1 1 d . . . . .
H1 H 0.205748 0.511389 0.620273 0.054 Uiso 1 1 calc R . . . .
C14 C 0.89881(14) 0.7752(3) 0.5974(2) 0.0458(6) Uani 1 1 d . . . . .
H14 H 0.867522 0.748914 0.530346 0.055 Uiso 1 1 calc R . . . .
C15 C 0.98213(15) 0.8211(4) 0.5970(2) 0.0580(7) Uani 1 1 d . . . . .
H15 H 1.007622 0.825350 0.529721 0.070 Uiso 1 1 calc R . . . .
C17 C 0.98597(14) 0.8533(4) 0.7944(2) 0.0563(7) Uani 1 1 d . . . . .
H17 H 1.016116 0.881873 0.861865 0.068 Uiso 1 1 calc R . . . .
C16 C 1.02693(15) 0.8604(4) 0.6975(3) 0.0617(8) Uani 1 1 d . . . . .
H16 H 1.083106 0.890830 0.699689 0.074 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
S3 C8 1.752(2) . ?
S3 C6 1.7663(19) . ?
S2 C7 1.7540(19) . ?
S2 C6 1.768(2) . ?
S1 C5 1.741(2) . ?
S1 C1 1.739(2) . ?
N1 C13 1.345(3) . ?
N1 C17 1.347(3) . ?
C7 C8 1.405(3) . ?
C7 C12 1.391(3) . ?
C8 C9 1.395(3) . ?
C6 C3 1.368(3) . ?
C3 C4 1.457(3) . ?
C3 C2 1.466(3) . ?
C9 C10 1.399(3) . ?
C12 C11 1.388(3) . ?
C10 C11 1.396(3) . ?
C10 C13 1.498(3) . ?
C4 C5 1.334(3) . ?
C13 C14 1.396(3) . ?
C2 C1 1.340(3) . ?
C14 C15 1.384(3) . ?
C15 C16 1.379(4) . ?
C17 C16 1.376(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 S3 C6 96.05(9) . . ?
C7 S2 C6 96.23(9) . . ?
C1 S1 C5 100.45(11) . . ?
C13 N1 C17 116.9(2) . . ?
C8 C7 S2 116.23(15) . . ?
C12 C7 S2 123.71(16) . . ?
C12 C7 C8 120.03(18) . . ?
C7 C8 S3 116.85(14) . . ?
C9 C8 S3 123.02(16) . . ?
C9 C8 C7 120.13(18) . . ?
S3 C6 S2 114.55(11) . . ?
C3 C6 S3 123.22(16) . . ?
C3 C6 S2 122.22(15) . . ?
C6 C3 C4 121.57(18) . . ?
C6 C3 C2 120.79(19) . . ?
C4 C3 C2 117.63(18) . . ?
C8 C9 C10 119.85(19) . . ?
C11 C12 C7 119.40(19) . . ?
C9 C10 C13 120.28(18) . . ?
C11 C10 C9 119.28(18) . . ?
C11 C10 C13 120.45(18) . . ?
C12 C11 C10 121.29(18) . . ?
C5 C4 C3 124.6(2) . . ?
N1 C13 C10 115.92(19) . . ?
N1 C13 C14 122.3(2) . . ?
C14 C13 C10 121.8(2) . . ?
C1 C2 C3 124.5(2) . . ?
C4 C5 S1 125.88(19) . . ?
C2 C1 S1 125.53(18) . . ?
C15 C14 C13 119.1(2) . . ?
C16 C15 C14 119.3(2) . . ?
N1 C17 C16 124.5(2) . . ?
C17 C16 C15 118.0(2) . . ?

_olex2_submission_original_sample_id Py-TP-BT
_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 1.382
_oxdiff_exptl_absorpt_empirical_full_min 0.852
####################################################################### 
# 
# 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_220711nishimoto4py-b
_database_code_depnum_ccdc_archive 'CCDC 2234244'
loop_
_audit_author_name
_audit_author_address
'Hiroshi Nishimoto'
;University of Hyogo
Japan
;
_audit_update_record             
;
2023-01-04 deposited with the CCDC.	2023-07-27 downloaded from the CCDC.
;
_audit_creation_date             2022-07-12
_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            4Py-TP-BT
_chemical_name_systematic        
5-(4-pyridyl)-2-(thiopyran-4-ylidene)-1,3-benzodithiole
_chemical_formula_moiety         'C17 H11 N S3'
_chemical_formula_sum            'C17 H11 N S3'
_chemical_formula_weight         325.45
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C17H11S3N1
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                   6.1579(3)
_cell_length_b                   7.5864(4)
_cell_length_c                   31.1475(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1455.10(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2392
_cell_measurement_temperature    298
_cell_measurement_theta_max      25.0280
_cell_measurement_theta_min      2.9640
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.500
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.60a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear intense orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0734
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       44
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_number            9443
_diffrn_reflns_point_group_measured_fraction_full 0.953
_diffrn_reflns_point_group_measured_fraction_max 0.880
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.408
_diffrn_reflns_theta_min         2.616
_diffrn_ambient_temperature      298
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -24.00   2.00   0.50   18.00    --   20.00  54.00  90.00   52
  2  ω    -74.00 -48.00   0.50   18.00    --   20.00  54.00-150.00   52
  3  ω     10.00 108.00   0.50   18.00    --   20.00  54.00-150.00  196
  4  ω    -74.00  44.00   0.50   18.00    --   20.00  54.00   0.00  236
  5  ω    -42.00 -17.00   0.50   18.00    --   20.00  54.00  60.00   50
  6  ω     34.00  62.00   0.50   18.00    --   20.00  54.00  60.00   56
  7  ω     65.00  90.00   0.50   18.00    --   20.00  54.00  60.00   50
  8  ω    -56.00 -31.00   0.50   18.00    --   20.00  54.00  90.00   50
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0094481000
_diffrn_orient_matrix_UB_12      0.0216743000
_diffrn_orient_matrix_UB_13      -0.0220654000
_diffrn_orient_matrix_UB_21      0.1099172000
_diffrn_orient_matrix_UB_22      -0.0245813000
_diffrn_orient_matrix_UB_23      -0.0032841000
_diffrn_orient_matrix_UB_31      -0.0332063000
_diffrn_orient_matrix_UB_32      -0.0875673000
_diffrn_orient_matrix_UB_33      -0.0045468000
_diffrn_oxdiff_digest_frames     
;
013cd3fa7c7290f2cbb8bb500171d0601500025036a
;
_diffrn_oxdiff_digest_hkl        
;
016d504e7fe6bdac2ba9744aa6700e7ad07a41
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.564
_reflns_Friedel_fraction_full    0.884
_reflns_Friedel_fraction_max     0.758
_reflns_number_gt                2305
_reflns_number_total             3875
_reflns_odcompleteness_completeness 99.78
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.40.60a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.60a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.60a (Rigaku OD, 2019)'
_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         0.363
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.060
_refine_ls_abs_structure_details 
;
 Flack x determined using 636 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.37(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3875
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1111
_refine_ls_R_factor_gt           0.0553
_refine_ls_restrained_S_all      0.997
_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)+(0.0528P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1038
_refine_ls_wR_factor_ref         0.1217
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C10(H10), C8(H8), C11(H11), C2(H2), C4(H4), C14(H14), C17(H17), C1(H1),
 C16(H16), C15(H15), C5(H5)
;
_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 0.54221(18) 0.39915(16) 0.54089(3) 0.0495(3) Uani 1 1 d . . . . .
S2 S 0.11225(17) 0.55622(16) 0.56089(4) 0.0494(3) Uani 1 1 d . . . . .
S3 S 0.5331(2) 0.50602(18) 0.72407(4) 0.0603(4) Uani 1 1 d . . . . .
N1 N 0.5512(7) 0.5002(5) 0.28810(11) 0.0548(10) Uani 1 1 d . . . . .
C12 C 0.1797(6) 0.5384(5) 0.50604(12) 0.0373(10) Uani 1 1 d . . . . .
C3 C 0.4180(6) 0.4912(5) 0.62354(12) 0.0368(9) Uani 1 1 d . . . . .
C7 C 0.3848(6) 0.4664(5) 0.49682(12) 0.0357(9) Uani 1 1 d . . . . .
C9 C 0.3241(6) 0.5112(6) 0.42037(13) 0.0388(10) Uani 1 1 d . . . . .
C13 C 0.4026(7) 0.5058(5) 0.37534(12) 0.0382(9) Uani 1 1 d . . . . .
C10 C 0.1160(6) 0.5786(5) 0.43145(13) 0.0419(10) Uani 1 1 d . . . . .
H10 H 0.024040 0.615453 0.409536 0.050 Uiso 1 1 calc R . . . .
C6 C 0.3675(6) 0.4848(5) 0.58092(13) 0.0384(10) Uani 1 1 d . . . . .
C8 C 0.4570(7) 0.4523(5) 0.45496(12) 0.0419(10) Uani 1 1 d . . . . .
H8 H 0.592981 0.404139 0.449339 0.050 Uiso 1 1 calc R . . . .
C11 C 0.0457(7) 0.5914(5) 0.47279(14) 0.0466(10) Uani 1 1 d . . . . .
H11 H -0.091954 0.635586 0.478654 0.056 Uiso 1 1 calc R . . . .
C2 C 0.6244(7) 0.4245(6) 0.64004(13) 0.0467(11) Uani 1 1 d . . . . .
H2 H 0.722462 0.379231 0.620198 0.056 Uiso 1 1 calc R . . . .
C4 C 0.2682(7) 0.5663(6) 0.65517(14) 0.0490(12) Uani 1 1 d . . . . .
H4 H 0.137527 0.611345 0.644960 0.059 Uiso 1 1 calc R . . . .
C14 C 0.5847(8) 0.4091(6) 0.36259(13) 0.0515(12) Uani 1 1 d . . . . .
H14 H 0.661305 0.342746 0.382621 0.062 Uiso 1 1 calc R . . . .
C17 C 0.2986(7) 0.5999(6) 0.34228(14) 0.0518(12) Uani 1 1 d . . . . .
H17 H 0.175901 0.667076 0.348270 0.062 Uiso 1 1 calc R . . . .
C1 C 0.6840(7) 0.4233(6) 0.68143(13) 0.0506(12) Uani 1 1 d . . . . .
H1 H 0.818192 0.373812 0.687912 0.061 Uiso 1 1 calc R . . . .
C16 C 0.3792(8) 0.5924(7) 0.30082(14) 0.0573(13) Uani 1 1 d . . . . .
H16 H 0.306514 0.657578 0.280015 0.069 Uiso 1 1 calc R . . . .
C15 C 0.6514(8) 0.4121(7) 0.31993(15) 0.0581(13) Uani 1 1 d . . . . .
H15 H 0.775143 0.348154 0.312840 0.070 Uiso 1 1 calc R . . . .
C5 C 0.3031(8) 0.5756(7) 0.69714(14) 0.0571(14) Uani 1 1 d . . . . .
H5 H 0.192891 0.624404 0.713730 0.068 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 C7 1.756(4) . ?
S1 C6 1.770(4) . ?
S2 C12 1.764(4) . ?
S2 C6 1.776(4) . ?
S3 C1 1.738(4) . ?
S3 C5 1.729(5) . ?
N1 C16 1.330(6) . ?
N1 C15 1.346(5) . ?
C12 C7 1.405(5) . ?
C12 C11 1.384(5) . ?
C3 C6 1.364(5) . ?
C3 C2 1.461(6) . ?
C3 C4 1.465(6) . ?
C7 C8 1.382(5) . ?
C9 C13 1.484(5) . ?
C9 C10 1.422(5) . ?
C9 C8 1.425(5) . ?
C13 C14 1.398(6) . ?
C13 C17 1.407(5) . ?
C10 C11 1.362(6) . ?
C2 C1 1.340(5) . ?
C4 C5 1.327(5) . ?
C14 C15 1.391(5) . ?
C17 C16 1.385(6) . ?

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 C6 96.23(18) . . ?
C12 S2 C6 96.22(18) . . ?
C5 S3 C1 100.2(2) . . ?
C16 N1 C15 114.0(4) . . ?
C7 C12 S2 116.1(3) . . ?
C11 C12 S2 124.2(3) . . ?
C11 C12 C7 119.7(4) . . ?
C6 C3 C2 121.9(4) . . ?
C6 C3 C4 121.6(4) . . ?
C2 C3 C4 116.5(4) . . ?
C12 C7 S1 116.7(3) . . ?
C8 C7 S1 122.5(3) . . ?
C8 C7 C12 120.8(4) . . ?
C10 C9 C13 122.2(4) . . ?
C10 C9 C8 116.6(4) . . ?
C8 C9 C13 121.2(4) . . ?
C14 C13 C9 123.0(4) . . ?
C14 C13 C17 115.1(4) . . ?
C17 C13 C9 121.9(4) . . ?
C11 C10 C9 122.8(4) . . ?
S1 C6 S2 113.7(2) . . ?
C3 C6 S1 124.0(3) . . ?
C3 C6 S2 122.2(3) . . ?
C7 C8 C9 120.3(4) . . ?
C10 C11 C12 119.8(4) . . ?
C1 C2 C3 125.4(4) . . ?
C5 C4 C3 125.5(4) . . ?
C15 C14 C13 120.0(4) . . ?
C16 C17 C13 119.9(4) . . ?
C2 C1 S3 125.9(4) . . ?
N1 C16 C17 125.8(4) . . ?
N1 C15 C14 125.2(4) . . ?
C4 C5 S3 126.5(4) . . ?

_olex2_submission_original_sample_id 220711nishimoto4Py-b
_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 1.101
_oxdiff_exptl_absorpt_empirical_full_min 0.924
