# Electronic Supplementary Material (ESI) for Nanoscale.
# 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_jp-01-81_auto
_database_code_depnum_ccdc_archive 'CCDC 2244309'
loop_
_audit_author_name
_audit_author_address
'Jarred Potter'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2023-02-24 deposited with the CCDC.	2023-04-06 downloaded from the CCDC.
;
_audit_creation_date             2023-01-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H14 S2'
_chemical_formula_sum            'C20 H14 S2'
_chemical_formula_weight         318.43
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H16 S2'
_chemical_oxdiff_usercomment     'Marcus for Jarred'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
S S 0.3331 0.5567 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.0180(2)
_cell_length_b                   7.9129(3)
_cell_length_c                   12.2528(5)
_cell_angle_alpha                84.363(3)
_cell_angle_beta                 87.988(4)
_cell_angle_gamma                84.405(4)
_cell_volume                     385.71(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    3446
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.8770
_cell_measurement_theta_min      3.6270
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.046
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78483
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'pale pink orange'
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             166
_exptl_crystal_size_max          0.256
_exptl_crystal_size_mid          0.167
_exptl_crystal_size_min          0.069
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.954
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4800
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.954
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.779
_diffrn_reflns_theta_min         3.626
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.954
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     59.00 117.00   0.50    0.40    --   45.48 146.00 148.00  116
  2  ω     89.00 114.00   0.50    1.00    --  102.69 146.00 148.00   50
  3  ω     74.00 175.00   0.50    1.00    --  102.69 125.00 -17.00  202
  4  ω     23.00 117.00   0.50    0.40    --   45.48  77.00 -30.00  188
  5  ω   -105.00 -24.00   0.50    0.40    --  -45.48 146.00 148.00  162
  6  ω    -93.00 -13.00   0.50    0.40    --  -45.48 125.00 -17.00  160
  7  ω   -111.00 -30.00   0.50    1.00    -- -102.69 125.00 -17.00  162
  8  ω    -73.00 -30.00   0.50    1.00    -- -102.69  61.00-150.00   86
  9  ω    -73.00 -30.00   0.50    1.00    -- -102.69  61.00-180.00   86
 10  ω   -177.00 -90.00   0.50    1.00    -- -102.69 -30.00 -60.00  174
 11  ω   -175.00 -86.00   0.50    1.00    -- -102.69 -61.00   0.00  178
 12  ω   -175.00 -83.00   0.50    1.00    -- -102.69 -94.00  30.00  184
 13  ω   -174.00 -90.00   0.50    1.00    -- -102.69 -45.00  90.00  168
 14  ω   -168.00 -59.00   0.50    1.00    -- -102.69-146.00  97.00  218
 15  ω   -117.00 -59.00   0.50    0.40    --  -45.48-146.00  97.00  116
 16  ω     24.00 106.00   0.50    0.40    --   45.48-146.00  97.00  164
 17  ω     30.00 127.00   0.50    1.00    --  102.69-146.00  97.00  194
 18  ω     30.00 105.00   0.50    1.00    --  102.69 -94.00  90.00  150
 19  ω     13.00  93.00   0.50    0.40    --   45.48-125.00 -96.00  160
 20  ω     30.00 111.00   0.50    1.00    --  102.69-125.00 -96.00  162
 21  ω     30.00 103.00   0.50    1.00    --  102.69 -77.00-120.00  146
 22  ω     65.00  94.00   0.50    1.00    --  102.69 -77.00 -90.00   58
 23  ω     30.00  69.00   0.50    1.00    --  102.69 -61.00-120.00   78
 24  ω    -29.00  24.00   0.50    0.40    --   45.48 -19.00-120.00  106
 25  ω    -29.00  24.00   0.50    0.40    --   45.48 -19.00   0.00  106
 26  ω     30.00  56.00   0.50    1.00    --  102.69 -61.00  90.00   52
 27  ω     30.00 103.00   0.50    1.00    --  102.69 -77.00  60.00  146
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1483740000
_diffrn_orient_matrix_UB_12      -0.1439896000
_diffrn_orient_matrix_UB_13      -0.0682813000
_diffrn_orient_matrix_UB_21      0.1145648000
_diffrn_orient_matrix_UB_22      -0.1079724000
_diffrn_orient_matrix_UB_23      0.1059109000
_diffrn_orient_matrix_UB_31      -0.3367123000
_diffrn_orient_matrix_UB_32      -0.0789171000
_diffrn_orient_matrix_UB_33      0.0096769000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1395
_reflns_number_total             1496
_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 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.072
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     101
_refine_ls_number_reflns         1496
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0382
_refine_ls_restrained_S_all      1.059
_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)+(0.0674P)²+0.1498P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1016
_refine_ls_wR_factor_ref         0.1033
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C14(H14), C12(H12), C11(H11)
1.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C)
;
_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 0.45846(10) 0.16386(5) 0.08921(3) 0.02287(18) Uani 1 1 d . . . . .
C3 C 0.9696(4) 0.9403(2) 0.47570(14) 0.0234(4) Uani 1 1 d . . . . .
C2 C 0.9004(4) 0.8080(2) 0.41936(14) 0.0236(4) Uani 1 1 d . . . . .
C1 C 0.8365(4) 0.6921(2) 0.36838(14) 0.0231(4) Uani 1 1 d . . . . .
C10 C 0.7519(4) 0.5613(2) 0.30475(14) 0.0213(4) Uani 1 1 d . . . . .
C15 C 0.8013(4) 0.5773(2) 0.19005(14) 0.0224(4) Uani 1 1 d . . . . .
H15 H 0.895828 0.674625 0.155042 0.027 Uiso 1 1 calc R U . . .
C14 C 0.7142(4) 0.4536(2) 0.12826(14) 0.0217(4) Uani 1 1 d . . . . .
H14 H 0.751835 0.465544 0.051032 0.026 Uiso 1 1 calc R U . . .
C13 C 0.5701(4) 0.3098(2) 0.17793(14) 0.0197(3) Uani 1 1 d . . . . .
C12 C 0.5240(4) 0.2917(2) 0.29204(14) 0.0225(4) Uani 1 1 d . . . . .
H12 H 0.430214 0.194055 0.326883 0.027 Uiso 1 1 calc R U . . .
C11 C 0.6147(4) 0.4156(2) 0.35413(14) 0.0228(4) Uani 1 1 d . . . . .
H11 H 0.583499 0.401736 0.431592 0.027 Uiso 1 1 calc R U . . .
C16 C 0.2869(4) 0.0015(2) 0.18129(15) 0.0251(4) Uani 1 1 d . . . . .
H16A H 0.212689 -0.086297 0.139076 0.038 Uiso 1 1 calc R U . . .
H16B H 0.096020 0.052555 0.222600 0.038 Uiso 1 1 calc R U . . .
H16C H 0.458499 -0.050406 0.232387 0.038 Uiso 1 1 calc R U . . .


_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 C13 1.7605(17) . ?
S1 C16 1.7980(17) . ?
C3 C3 1.213(4) 2_776 ?
C3 C2 1.364(3) . ?
C2 C1 1.211(3) . ?
C1 C10 1.429(2) . ?
C10 C15 1.407(2) . ?
C10 C11 1.401(2) . ?
C15 H15 0.9500 . ?
C15 C14 1.373(2) . ?
C14 H14 0.9500 . ?
C14 C13 1.403(2) . ?
C13 C12 1.399(2) . ?
C12 H12 0.9500 . ?
C12 C11 1.381(2) . ?
C11 H11 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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
C13 S1 C16 103.12(8) . . ?
C3 C3 C2 179.0(2) 2_776 . ?
C1 C2 C3 179.13(19) . . ?
C2 C1 C10 177.24(18) . . ?
C15 C10 C1 120.40(15) . . ?
C11 C10 C1 121.23(15) . . ?
C11 C10 C15 118.36(16) . . ?
C10 C15 H15 119.7 . . ?
C14 C15 C10 120.66(15) . . ?
C14 C15 H15 119.7 . . ?
C15 C14 H14 119.6 . . ?
C15 C14 C13 120.71(15) . . ?
C13 C14 H14 119.6 . . ?
C14 C13 S1 116.25(13) . . ?
C12 C13 S1 124.71(13) . . ?
C12 C13 C14 119.03(15) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 C13 120.13(15) . . ?
C11 C12 H12 119.9 . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 121.08(15) . . ?
C12 C11 H11 119.5 . . ?
S1 C16 H16A 109.5 . . ?
S1 C16 H16B 109.5 . . ?
S1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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 C13 C12 C11 -178.76(12) . . . . ?
C1 C10 C15 C14 -178.66(15) . . . . ?
C1 C10 C11 C12 178.06(15) . . . . ?
C10 C15 C14 C13 0.8(3) . . . . ?
C15 C10 C11 C12 -1.1(2) . . . . ?
C15 C14 C13 S1 178.18(12) . . . . ?
C15 C14 C13 C12 -1.7(3) . . . . ?
C14 C13 C12 C11 1.1(3) . . . . ?
C13 C12 C11 C10 0.3(3) . . . . ?
C11 C10 C15 C14 0.5(2) . . . . ?
C16 S1 C13 C14 179.98(13) . . . . ?
C16 S1 C13 C12 -0.20(17) . . . . ?

_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 1.674
_oxdiff_exptl_absorpt_empirical_full_min 0.787
####################################################################### 
# 
# 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_jp-01-51
_database_code_depnum_ccdc_archive 'CCDC 2244310'
loop_
_audit_author_name
_audit_author_address
'Jarred Potter'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2023-02-24 deposited with the CCDC.	2023-04-06 downloaded from the CCDC.
;
_audit_creation_date             2023-01-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C22 H14 S2'
_chemical_formula_sum            'C22 H14 S2'
_chemical_formula_weight         342.45
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 S2'
_chemical_oxdiff_usercomment     'Marcus for Jarred'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
S S 0.3331 0.5567 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   4.0524(2)
_cell_length_b                   8.0222(3)
_cell_length_c                   13.5176(7)
_cell_angle_alpha                75.943(4)
_cell_angle_beta                 84.880(4)
_cell_angle_gamma                83.356(4)
_cell_volume                     422.57(4)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    2796
_cell_measurement_temperature    102(4)
_cell_measurement_theta_max      72.8650
_cell_measurement_theta_min      3.3820
_shelx_estimated_absorpt_T_max   0.920
_shelx_estimated_absorpt_T_min   0.495
_exptl_absorpt_coefficient_mu    2.822
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.402
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear intense yellow'
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             178
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 3 3 0.0392
2 -3 -3 0.0196
1 4 -1 0.1275
-1 -5 1 0.1092
0 0 8 0.0160
0 0 -9 0.0119

_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.03
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2.0344 2.5826 2.5875 -0.7579 -0.5813 0.2961
2.0344 -2.5826 -2.5875 0.7579 0.5813 -0.2961
1.1372 4.4646 -1.3083 0.1946 0.1480 0.9697
-0.7681 -4.7956 0.8421 -0.0624 -0.0467 -0.9970
0.1146 -0.1747 8.4344 0.3128 -0.8859 -0.3426
-0.1394 -0.0162 -8.5178 -0.3169 0.8972 0.3076

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.944
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            4532
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.944
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.480
_diffrn_reflns_theta_min         3.377
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      102(4)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -79.00  23.00   0.50    0.50    --  -46.07  99.00 -20.00  204
  2  ω    -23.00  80.00   0.50    0.50    --   46.07 -99.00-126.00  206
  3  ω   -174.00 -86.00   0.50    3.00    -- -102.29 -99.00-126.00  176
  4  ω   -106.00 -30.00   0.50    3.00    -- -102.29  99.00 -20.00  152
  5  ω     86.00 174.00   0.50    3.00    --  102.29  99.00 -20.00  176
  6  ω     30.00 106.00   0.50    3.00    --  102.29 -99.00-126.00  152
  7  ω   -118.00 -31.00   0.50    0.50    --  -46.07 -57.00  90.00  174
  8  ω   -119.00 -73.00   0.50    0.50    --  -46.07-125.00  30.00   92
  9  ω    -26.00  29.00   0.50    0.50    --  -46.07  19.00-120.00  110
 10  ω    -28.00  26.00   0.50    0.50    --   46.07 -19.00-150.00  108
 11  ω     13.00  94.00   0.50    0.50    --   46.07-125.00-180.00  162
 12  ω   -108.00 -33.00   0.50    3.00    -- -102.29 125.00  30.00  150
 13  ω   -102.00 -76.00   0.50    3.00    -- -102.29 125.00 120.00   52
 14  ω   -166.00-130.00   0.50    3.00    -- -102.29 -62.00 112.26   72
 15  ω    -69.00 -33.00   0.50    3.00    -- -102.29  61.00  60.00   72
 16  ω   -126.00 -60.00   0.50    3.00    -- -102.29 145.00-141.42  132
 17  ω    -69.00 -30.00   0.50    3.00    -- -102.29  61.00-120.00   78
 18  ω   -145.00 -84.00   0.50    3.00    -- -102.29 -77.00 -30.00  122
 19  ω     30.00  78.00   0.50    3.00    --  102.29-125.00   0.00   96
 20  ω     40.00  71.00   0.50    3.00    --  102.29 -61.00-120.00   62
 21  ω     78.00 103.00   0.50    3.00    --  102.29 -94.00-180.00   50
 22  ω     31.00  80.00   0.50    3.00    --  102.29-125.00-150.00   98
 23  ω     30.00  72.00   0.50    3.00    --  102.29 -94.00 120.00   84
 24  ω    100.00 174.00   0.50    3.00    --  102.29  45.00 120.00  148
 25  ω     37.00 101.00   0.50    3.00    --  102.29 -77.00 -30.00  128
 26  ω     89.00 175.00   0.50    3.00    --  102.29  15.00 -90.00  172
 27  ω     32.00  60.00   0.50    3.00    --  102.29 -61.00 120.00   56
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.3622716000
_diffrn_orient_matrix_UB_12      -0.0395076000
_diffrn_orient_matrix_UB_13      0.0313468000
_diffrn_orient_matrix_UB_21      0.1146050000
_diffrn_orient_matrix_UB_22      -0.0274366000
_diffrn_orient_matrix_UB_23      -0.1071546000
_diffrn_orient_matrix_UB_31      0.0519826000
_diffrn_orient_matrix_UB_32      0.1930067000
_diffrn_orient_matrix_UB_33      -0.0373343000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1511
_reflns_number_total             1637
_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 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_refine_diff_density_max         0.325
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.103
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1637
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0358
_refine_ls_R_factor_gt           0.0330
_refine_ls_restrained_S_all      1.103
_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)+(0.0543P)²+0.0927P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0904
_refine_ls_wR_factor_ref         0.0919
_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:
 C15(H6), C14(H7), C12(H9), C11(H10)
2.b Idealised Me refined as rotating group:
 C16(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.55334(9) 0.85736(4) 0.91743(3) 0.02247(15) Uani 1 1 d . . . . .
C4 C 0.0292(4) 0.06130(19) 0.52414(12) 0.0233(3) Uani 1 1 d . . . . .
C3 C 0.0819(4) 0.17120(19) 0.56715(12) 0.0232(3) Uani 1 1 d . . . . .
C2 C 0.1472(4) 0.29080(19) 0.61688(12) 0.0231(3) Uani 1 1 d . . . . .
C1 C 0.2135(4) 0.39309(19) 0.66335(12) 0.0223(3) Uani 1 1 d . . . . .
C10 C 0.2933(4) 0.50745(19) 0.72142(12) 0.0210(3) Uani 1 1 d . . . . .
C15 C 0.2206(4) 0.47198(19) 0.82748(12) 0.0216(3) Uani 1 1 d . . . . .
H6 H 0.116034 0.371286 0.860662 0.026 Uiso 1 1 calc R U . . .
C14 C 0.2993(4) 0.58178(19) 0.88376(12) 0.0216(3) Uani 1 1 d . . . . .
H7 H 0.246817 0.556654 0.955422 0.026 Uiso 1 1 calc R U . . .
C13 C 0.4566(4) 0.73071(19) 0.83654(12) 0.0201(3) Uani 1 1 d . . . . .
C12 C 0.5274(4) 0.76687(19) 0.73083(12) 0.0216(3) Uani 1 1 d . . . . .
H9 H 0.631198 0.867800 0.697655 0.026 Uiso 1 1 calc R U . . .
C11 C 0.4473(4) 0.6568(2) 0.67427(12) 0.0225(3) Uani 1 1 d . . . . .
H10 H 0.497370 0.682728 0.602491 0.027 Uiso 1 1 calc R U . . .
C16 C 0.7339(4) 1.03606(19) 0.83043(13) 0.0254(3) Uani 1 1 d . . . . .
H11A H 0.571049 1.097436 0.781471 0.038 Uiso 1 1 calc R U . . .
H11B H 0.931873 0.992829 0.793562 0.038 Uiso 1 1 calc R U . . .
H11C H 0.797063 1.115162 0.868908 0.038 Uiso 1 1 calc R U . . .


_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 C13 1.7578(15) . ?
S1 C16 1.8011(16) . ?
C4 C4 1.357(3) 2_556 ?
C4 C3 1.215(2) . ?
C3 C2 1.359(2) . ?
C2 C1 1.213(2) . ?
C1 C10 1.423(2) . ?
C10 C15 1.403(2) . ?
C10 C11 1.401(2) . ?
C15 H6 0.9500 . ?
C15 C14 1.375(2) . ?
C14 H7 0.9500 . ?
C14 C13 1.405(2) . ?
C13 C12 1.397(2) . ?
C12 H9 0.9500 . ?
C12 C11 1.381(2) . ?
C11 H10 0.9500 . ?
C16 H11A 0.9800 . ?
C16 H11B 0.9800 . ?
C16 H11C 0.9800 . ?

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
C13 S1 C16 103.32(8) . . ?
C3 C4 C4 179.8(2) . 2_556 ?
C4 C3 C2 178.37(17) . . ?
C1 C2 C3 177.62(17) . . ?
C2 C1 C10 177.67(16) . . ?
C15 C10 C1 120.47(13) . . ?
C11 C10 C1 120.89(15) . . ?
C11 C10 C15 118.63(14) . . ?
C10 C15 H6 119.7 . . ?
C14 C15 C10 120.54(14) . . ?
C14 C15 H6 119.7 . . ?
C15 C14 H7 119.6 . . ?
C15 C14 C13 120.77(15) . . ?
C13 C14 H7 119.6 . . ?
C14 C13 S1 116.30(12) . . ?
C12 C13 S1 124.92(12) . . ?
C12 C13 C14 118.78(14) . . ?
C13 C12 H9 119.8 . . ?
C11 C12 C13 120.43(14) . . ?
C11 C12 H9 119.8 . . ?
C10 C11 H10 119.6 . . ?
C12 C11 C10 120.84(15) . . ?
C12 C11 H10 119.6 . . ?
S1 C16 H11A 109.5 . . ?
S1 C16 H11B 109.5 . . ?
S1 C16 H11C 109.5 . . ?
H11A C16 H11B 109.5 . . ?
H11A C16 H11C 109.5 . . ?
H11B C16 H11C 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 C13 C12 C11 178.58(11) . . . . ?
C1 C10 C15 C14 179.60(14) . . . . ?
C1 C10 C11 C12 -179.41(14) . . . . ?
C10 C15 C14 C13 -0.6(2) . . . . ?
C15 C10 C11 C12 0.2(2) . . . . ?
C15 C14 C13 S1 -178.45(11) . . . . ?
C15 C14 C13 C12 1.0(2) . . . . ?
C14 C13 C12 C11 -0.8(2) . . . . ?
C13 C12 C11 C10 0.2(2) . . . . ?
C11 C10 C15 C14 0.0(2) . . . . ?
C16 S1 C13 C14 -178.04(12) . . . . ?
C16 S1 C13 C12 2.60(15) . . . . ?

_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 1.430
_oxdiff_exptl_absorpt_empirical_full_min 0.757
####################################################################### 
# 
# 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_jp-01-42
_database_code_depnum_ccdc_archive 'CCDC 2244311'
loop_
_audit_author_name
_audit_author_address
'Jarred Potter'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2023-02-24 deposited with the CCDC.	2023-04-06 downloaded from the CCDC.
;
_audit_creation_date             2023-01-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C28 H28 O2 S2)'
_chemical_formula_sum            'C14 H14 O S'
_chemical_formula_weight         230.31
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 S1'
_chemical_oxdiff_usercomment     'Marcus for Jarred'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.39700(10)
_cell_length_b                   9.82200(10)
_cell_length_c                   18.7581(3)
_cell_angle_alpha                94.6200(10)
_cell_angle_beta                 98.4700(10)
_cell_angle_gamma                110.8710(10)
_cell_volume                     1246.41(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    16859
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.9370
_cell_measurement_theta_min      4.8010
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.099
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83302
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear intense yellow'
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.001
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_unetI/netI     0.0203
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            23701
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.973
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.366
_diffrn_reflns_theta_min         4.817
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.973
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     24.00 118.00   0.50    0.10    --   46.32  77.00-120.00  188
  2  ω     89.00 177.00   0.50    0.20    --  102.29  15.00-120.00  176
  3  ω     24.00 118.00   0.50    0.10    --   46.32  77.00  60.00  188
  4  ω     90.00 174.00   0.50    0.20    --  102.29  45.00 150.00  168
  5  ω     24.00  70.00   0.50    0.10    --   46.32  77.00 150.00   92
  6  ω    -69.00  26.00   0.50    0.10    --  -46.32  77.00 -60.00  190
  7  ω    -43.00  27.00   0.50    0.10    --  -46.32  38.00 -90.00  140
  8  ω    -43.00  27.00   0.50    0.10    --  -46.32  38.00   0.00  140
  9  ω     83.00 174.00   0.50    0.20    --  102.29 107.00   1.00  182
 10  ω     30.00 105.00   0.50    0.20    --  102.29 -77.00 -90.00  150
 11  ω     30.00  71.00   0.50    0.20    --  102.29 -61.00-120.00   82
 12  ω    -28.00  26.00   0.50    0.10    --   46.32 -19.00-180.00  108
 13  ω    -28.00  26.00   0.50    0.10    --   46.32 -19.00 120.00  108
 14  ω     30.00  71.00   0.50    0.20    --  102.29 -61.00 150.00   82
 15  ω     30.00  71.00   0.50    0.20    --  102.29 -61.00  30.00   82
 16  ω     30.00 111.00   0.50    0.20    --  102.29-125.00 120.00  162
 17  ω     30.00 108.00   0.50    0.20    --  102.29-106.00 141.33  156
 18  ω     -1.00  84.00   0.50    0.10    --   46.32-107.00 -96.00  170
 19  ω     30.00 111.00   0.50    0.20    --  102.29-125.00-150.00  162
 20  ω     30.00 105.00   0.50    0.20    --  102.29 -94.00-180.00  150
 21  ω     30.00 105.00   0.50    0.20    --  102.29 -94.00-120.00  150
 22  ω     30.00 107.00   0.50    0.20    --  102.29-107.00 -96.00  154
 23  ω     30.00 105.00   0.50    0.20    --  102.29 -94.00 -60.00  150
 24  ω     30.00 105.00   0.50    0.20    --  102.29 -94.00   0.00  150
 25  ω     30.00 105.00   0.50    0.20    --  102.29 -94.00  90.00  150
 26  ω   -111.00 -30.00   0.50    0.20    -- -102.29 125.00-150.00  162
 27  ω    -84.00   1.00   0.50    0.10    --  -46.32 107.00   1.00  170
 28  ω   -109.00 -30.00   0.50    0.20    -- -102.29 115.00  54.96  158
 29  ω   -107.00 -30.00   0.50    0.20    -- -102.29 107.00   1.00  154
 30  ω    -71.00 -30.00   0.50    0.20    -- -102.29  61.00  30.00   82
 31  ω    -71.00 -30.00   0.50    0.20    -- -102.29  61.00  90.00   82
 32  ω    -71.00 -30.00   0.50    0.20    -- -102.29  61.00  60.00   82
 33  ω   -176.00 -90.00   0.50    0.20    -- -102.29 -30.00 150.00  172
 34  ω   -174.00 -89.00   0.50    0.20    -- -102.29 -49.00 -27.93  170
 35  ω   -174.00 -90.00   0.50    0.20    -- -102.29 -45.00 -60.00  168
 36  ω   -174.00 -89.00   0.50    0.20    -- -102.29 -51.00-167.52  170
 37  ω   -174.00 -83.00   0.50    0.20    -- -102.29-107.00 -96.00  182
 38  ω   -118.00 -73.00   0.50    0.10    --  -46.32-125.00   0.00   90
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1945700000
_diffrn_orient_matrix_UB_12      0.0790147000
_diffrn_orient_matrix_UB_13      0.0549122000
_diffrn_orient_matrix_UB_21      0.1168528000
_diffrn_orient_matrix_UB_22      -0.0125320000
_diffrn_orient_matrix_UB_23      -0.0600918000
_diffrn_orient_matrix_UB_31      0.0031278000
_diffrn_orient_matrix_UB_32      0.1495785000
_diffrn_orient_matrix_UB_33      -0.0203467000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4744
_reflns_number_total             5032
_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 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         5032
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0330
_refine_ls_R_factor_gt           0.0315
_refine_ls_restrained_S_all      1.048
_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)+(0.0434P)²+0.4291P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0833
_refine_ls_wR_factor_ref         0.0845
_refine_special_details          ?
_olex2_refinement_description    
;
1. Restrained distances
 O101-H101 = O101-H10A = O1-H1A = O1-H1B
 0.95 with sigma of 0.002
2. Others
 Fixed Sof: H1A(0.5) H1B(0.5) H101(0.5) H10A(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C14(H14), C12(H12), C11(H11), C115(H115), C114(H114), C112(H112),
 C111(H111)
3.b Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C32(H32A,H32B,H32C), C31(H31A,H31B,H31C), C116(H11A,H11B,
 H11C), C131(H13A,H13B,H13C), C132(H13D,H13E,H13F)
;
_atom_sites_solution_hydrogens   mixed
_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 -0.98995(4) -0.30337(3) -0.00220(2) 0.02575(9) Uani 1 1 d . . . . .
O1 O 0.44378(14) 0.08976(14) 0.45348(5) 0.0391(3) Uani 1 1 d D . . . .
H1A H 0.317(2) 0.085(4) 0.460(2) 0.055(11) Uiso 0.5 1 d D . P A 1
H1B H 0.500(6) 0.047(4) 0.4896(18) 0.068(14) Uiso 0.5 1 d D . P B 2
C4 C 0.28506(18) 0.03686(13) 0.32914(6) 0.0203(2) Uani 1 1 d . . . . .
C3 C 0.12967(18) -0.00912(13) 0.28709(6) 0.0208(2) Uani 1 1 d . . . . .
C2 C -0.04898(18) -0.06123(13) 0.23976(6) 0.0206(2) Uani 1 1 d . . . . .
C1 C -0.20599(18) -0.10523(12) 0.19851(6) 0.0206(2) Uani 1 1 d . . . . .
C10 C -0.39422(17) -0.15705(12) 0.15118(6) 0.0196(2) Uani 1 1 d . . . . .
C15 C -0.41113(18) -0.14384(14) 0.07671(7) 0.0239(3) Uani 1 1 d . . . . .
H15 H -0.295747 -0.100864 0.057110 0.029 Uiso 1 1 calc R U . . .
C14 C -0.59386(18) -0.19272(14) 0.03174(7) 0.0249(3) Uani 1 1 d . . . . .
H14 H -0.602891 -0.183802 -0.018590 0.030 Uiso 1 1 calc R U . . .
C13 C -0.76646(17) -0.25546(13) 0.05958(7) 0.0208(2) Uani 1 1 d . . . . .
C12 C -0.75017(18) -0.27143(13) 0.13315(7) 0.0224(2) Uani 1 1 d . . . . .
H12 H -0.865511 -0.316042 0.152522 0.027 Uiso 1 1 calc R U . . .
C11 C -0.56686(18) -0.22265(13) 0.17812(7) 0.0220(2) Uani 1 1 d . . . . .
H11 H -0.558068 -0.233908 0.228191 0.026 Uiso 1 1 calc R U . . .
C16 C -1.17225(19) -0.39320(15) 0.05000(8) 0.0296(3) Uani 1 1 d . . . . .
H16A H -1.303772 -0.426235 0.019492 0.044 Uiso 1 1 calc R U . . .
H16B H -1.163870 -0.323986 0.092162 0.044 Uiso 1 1 calc R U . . .
H16C H -1.148431 -0.478336 0.066787 0.044 Uiso 1 1 calc R U . . .
C30 C 0.47646(17) 0.10137(13) 0.38049(6) 0.0182(2) Uani 1 1 d . . . . .
C32 C 0.60923(19) 0.01933(14) 0.36482(8) 0.0273(3) Uani 1 1 d . . . . .
H32A H 0.632454 0.026417 0.314908 0.041 Uiso 1 1 calc R U . . .
H32B H 0.545572 -0.084405 0.370369 0.041 Uiso 1 1 calc R U . . .
H32C H 0.735246 0.063105 0.399092 0.041 Uiso 1 1 calc R U . . .
C31 C 0.5714(2) 0.26388(13) 0.37344(7) 0.0279(3) Uani 1 1 d . . . . .
H31A H 0.482681 0.313969 0.383622 0.042 Uiso 1 1 calc R U . . .
H31B H 0.596223 0.273705 0.323861 0.042 Uiso 1 1 calc R U . . .
H31C H 0.696216 0.308516 0.408315 0.042 Uiso 1 1 calc R U . . .
S101 S 1.66097(4) 0.70806(3) 0.86356(2) 0.02796(9) Uani 1 1 d . . . . .
O101 O 0.12283(13) 0.13285(9) 0.48691(6) 0.0313(2) Uani 1 1 d D . . . .
H101 H 0.020(4) 0.042(2) 0.489(2) 0.046(10) Uiso 0.5 1 d D . P C 1
H10A H 0.249(2) 0.133(4) 0.482(2) 0.051(11) Uiso 0.5 1 d D . P D 2
C104 C 0.32508(17) 0.32697(12) 0.58131(6) 0.0191(2) Uani 1 1 d . . . . .
C103 C 0.47873(17) 0.37728(12) 0.62395(6) 0.0195(2) Uani 1 1 d . . . . .
C102 C 0.65913(17) 0.43489(12) 0.66990(6) 0.0203(2) Uani 1 1 d . . . . .
C101 C 0.82213(17) 0.48742(13) 0.70699(6) 0.0211(2) Uani 1 1 d . . . . .
C110 C 1.02027(17) 0.54438(13) 0.74701(6) 0.0197(2) Uani 1 1 d . . . . .
C115 C 1.12982(18) 0.45345(13) 0.75062(6) 0.0213(2) Uani 1 1 d . . . . .
H115 H 1.070146 0.353727 0.728161 0.026 Uiso 1 1 calc R U . . .
C114 C 1.32338(18) 0.50759(13) 0.78650(7) 0.0218(2) Uani 1 1 d . . . . .
H114 H 1.396012 0.444907 0.788419 0.026 Uiso 1 1 calc R U . . .
C113 C 1.41384(17) 0.65421(13) 0.82016(6) 0.0203(2) Uani 1 1 d . . . . .
C112 C 1.30511(18) 0.74483(13) 0.81710(7) 0.0218(2) Uani 1 1 d . . . . .
H112 H 1.364721 0.844339 0.839879 0.026 Uiso 1 1 calc R U . . .
C111 C 1.11022(18) 0.69033(13) 0.78093(7) 0.0219(2) Uani 1 1 d . . . . .
H111 H 1.037405 0.752889 0.779241 0.026 Uiso 1 1 calc R U . . .
C116 C 1.73925(19) 0.90372(14) 0.88759(7) 0.0278(3) Uani 1 1 d . . . . .
H11A H 1.719749 0.948309 0.843641 0.042 Uiso 1 1 calc R U . . .
H11B H 1.879128 0.944610 0.910369 0.042 Uiso 1 1 calc R U . . .
H11C H 1.661622 0.925070 0.921885 0.042 Uiso 1 1 calc R U . . .
C130 C 0.14362(16) 0.27181(12) 0.52466(6) 0.0172(2) Uani 1 1 d . . . . .
C131 C 0.16334(19) 0.37932(13) 0.46935(7) 0.0256(3) Uani 1 1 d . . . . .
H13A H 0.281872 0.391403 0.448994 0.038 Uiso 1 1 calc R U . . .
H13B H 0.173611 0.474830 0.493411 0.038 Uiso 1 1 calc R U . . .
H13C H 0.047226 0.340839 0.430095 0.038 Uiso 1 1 calc R U . . .
C132 C -0.03646(18) 0.25168(16) 0.55923(7) 0.0267(3) Uani 1 1 d . . . . .
H13D H -0.155294 0.215078 0.521163 0.040 Uiso 1 1 calc R U . . .
H13E H -0.023662 0.346386 0.585078 0.040 Uiso 1 1 calc R U . . .
H13F H -0.046252 0.180628 0.593685 0.040 Uiso 1 1 calc R U . . .


_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 C13 1.7581(12) . ?
S1 C16 1.7989(14) . ?
O1 H1A 0.949(2) . ?
O1 H1B 0.949(2) . ?
O1 C30 1.4315(14) . ?
C4 C3 1.2054(17) . ?
C4 C30 1.4814(16) . ?
C3 C2 1.3768(17) . ?
C2 C1 1.2076(17) . ?
C1 C10 1.4296(16) . ?
C10 C15 1.4047(17) . ?
C10 C11 1.3991(16) . ?
C15 H15 0.9500 . ?
C15 C14 1.3804(17) . ?
C14 H14 0.9500 . ?
C14 C13 1.4036(17) . ?
C13 C12 1.3940(17) . ?
C12 H12 0.9500 . ?
C12 C11 1.3837(17) . ?
C11 H11 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C30 C32 1.5202(16) . ?
C30 C31 1.5235(17) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
S101 C113 1.7571(12) . ?
S101 C116 1.7951(14) . ?
O101 H101 0.949(2) . ?
O101 H10A 0.949(2) . ?
O101 C130 1.4320(14) . ?
C104 C103 1.2017(17) . ?
C104 C130 1.4809(16) . ?
C103 C102 1.3742(17) . ?
C102 C101 1.2066(17) . ?
C101 C110 1.4313(16) . ?
C110 C115 1.4029(16) . ?
C110 C111 1.3969(17) . ?
C115 H115 0.9500 . ?
C115 C114 1.3790(17) . ?
C114 H114 0.9500 . ?
C114 C113 1.4010(17) . ?
C113 C112 1.3953(17) . ?
C112 H112 0.9500 . ?
C112 C111 1.3887(17) . ?
C111 H111 0.9500 . ?
C116 H11A 0.9800 . ?
C116 H11B 0.9800 . ?
C116 H11C 0.9800 . ?
C130 C131 1.5245(16) . ?
C130 C132 1.5236(16) . ?
C131 H13A 0.9800 . ?
C131 H13B 0.9800 . ?
C131 H13C 0.9800 . ?
C132 H13D 0.9800 . ?
C132 H13E 0.9800 . ?
C132 H13F 0.9800 . ?

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
C13 S1 C16 103.29(6) . . ?
C30 O1 H1A 115(2) . . ?
C30 O1 H1B 129(3) . . ?
C3 C4 C30 176.97(12) . . ?
C4 C3 C2 179.26(13) . . ?
C1 C2 C3 179.14(13) . . ?
C2 C1 C10 178.57(12) . . ?
C15 C10 C1 121.16(11) . . ?
C11 C10 C1 120.57(11) . . ?
C11 C10 C15 118.27(11) . . ?
C10 C15 H15 119.7 . . ?
C14 C15 C10 120.61(11) . . ?
C14 C15 H15 119.7 . . ?
C15 C14 H14 119.6 . . ?
C15 C14 C13 120.72(11) . . ?
C13 C14 H14 119.6 . . ?
C14 C13 S1 116.22(9) . . ?
C12 C13 S1 124.91(9) . . ?
C12 C13 C14 118.84(11) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 C13 120.34(11) . . ?
C11 C12 H12 119.8 . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.20(11) . . ?
C12 C11 H11 119.4 . . ?
S1 C16 H16A 109.5 . . ?
S1 C16 H16B 109.5 . . ?
S1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O1 C30 C4 109.40(9) . . ?
O1 C30 C32 108.76(10) . . ?
O1 C30 C31 108.45(10) . . ?
C4 C30 C32 110.29(10) . . ?
C4 C30 C31 108.74(9) . . ?
C32 C30 C31 111.16(10) . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
C113 S101 C116 103.67(6) . . ?
C130 O101 H101 124(2) . . ?
C130 O101 H10A 110(2) . . ?
C103 C104 C130 175.56(12) . . ?
C104 C103 C102 177.20(12) . . ?
C101 C102 C103 176.45(12) . . ?
C102 C101 C110 175.79(13) . . ?
C115 C110 C101 119.56(11) . . ?
C111 C110 C101 121.59(11) . . ?
C111 C110 C115 118.82(11) . . ?
C110 C115 H115 119.7 . . ?
C114 C115 C110 120.57(11) . . ?
C114 C115 H115 119.7 . . ?
C115 C114 H114 119.7 . . ?
C115 C114 C113 120.57(11) . . ?
C113 C114 H114 119.7 . . ?
C114 C113 S101 115.59(9) . . ?
C112 C113 S101 125.35(9) . . ?
C112 C113 C114 119.06(11) . . ?
C113 C112 H112 119.8 . . ?
C111 C112 C113 120.36(11) . . ?
C111 C112 H112 119.8 . . ?
C110 C111 H111 119.7 . . ?
C112 C111 C110 120.60(11) . . ?
C112 C111 H111 119.7 . . ?
S101 C116 H11A 109.5 . . ?
S101 C116 H11B 109.5 . . ?
S101 C116 H11C 109.5 . . ?
H11A C116 H11B 109.5 . . ?
H11A C116 H11C 109.5 . . ?
H11B C116 H11C 109.5 . . ?
O101 C130 C104 109.39(9) . . ?
O101 C130 C131 107.66(10) . . ?
O101 C130 C132 108.91(10) . . ?
C104 C130 C131 108.88(9) . . ?
C104 C130 C132 110.37(10) . . ?
C132 C130 C131 111.56(10) . . ?
C130 C131 H13A 109.5 . . ?
C130 C131 H13B 109.5 . . ?
C130 C131 H13C 109.5 . . ?
H13A C131 H13B 109.5 . . ?
H13A C131 H13C 109.5 . . ?
H13B C131 H13C 109.5 . . ?
C130 C132 H13D 109.5 . . ?
C130 C132 H13E 109.5 . . ?
C130 C132 H13F 109.5 . . ?
H13D C132 H13E 109.5 . . ?
H13D C132 H13F 109.5 . . ?
H13E C132 H13F 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 C13 C12 C11 -176.38(9) . . . . ?
C1 C10 C15 C14 -179.23(11) . . . . ?
C1 C10 C11 C12 179.08(11) . . . . ?
C10 C15 C14 C13 0.53(19) . . . . ?
C15 C10 C11 C12 -0.99(17) . . . . ?
C15 C14 C13 S1 176.41(10) . . . . ?
C15 C14 C13 C12 -1.78(19) . . . . ?
C14 C13 C12 C11 1.64(18) . . . . ?
C13 C12 C11 C10 -0.26(18) . . . . ?
C11 C10 C15 C14 0.85(18) . . . . ?
C16 S1 C13 C14 175.08(10) . . . . ?
C16 S1 C13 C12 -6.86(12) . . . . ?
S101 C113 C112 C111 179.79(9) . . . . ?
C101 C110 C115 C114 177.50(11) . . . . ?
C101 C110 C111 C112 -177.50(11) . . . . ?
C110 C115 C114 C113 0.19(18) . . . . ?
C115 C110 C111 C112 0.51(17) . . . . ?
C115 C114 C113 S101 -179.82(9) . . . . ?
C115 C114 C113 C112 0.21(18) . . . . ?
C114 C113 C112 C111 -0.25(18) . . . . ?
C113 C112 C111 C110 -0.12(18) . . . . ?
C111 C110 C115 C114 -0.54(17) . . . . ?
C116 S101 C113 C114 171.46(9) . . . . ?
C116 S101 C113 C112 -8.57(12) . . . . ?

_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 1.291
_oxdiff_exptl_absorpt_empirical_full_min 0.841
####################################################################### 
# 
# 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_jp-02-5
_database_code_depnum_ccdc_archive 'CCDC 2244315'
loop_
_audit_author_name
_audit_author_address
'Jarred Potter'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2023-02-24 deposited with the CCDC.	2023-04-06 downloaded from the CCDC.
;
_audit_creation_date             2023-01-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H8 N2'
_chemical_formula_sum            'C16 H8 N2'
_chemical_formula_weight         228.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2'
_chemical_oxdiff_usercomment     'Marcus for Jarred'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 '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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   3.80550(10)
_cell_length_b                   25.5128(10)
_cell_length_c                   5.9500(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.327(3)
_cell_angle_gamma                90
_cell_volume                     576.71(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2372
_cell_measurement_temperature    103(4)
_cell_measurement_theta_max      74.4970
_cell_measurement_theta_min      3.4570
_shelx_estimated_absorpt_T_max   0.964
_shelx_estimated_absorpt_T_min   0.870
_exptl_absorpt_coefficient_mu    0.621
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.626
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             236
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 2 -4 0.0851
-2 -1 -1 0.0505
1 16 1 0.0292
0 -16 -1 0.0038
0 5 -4 0.0916
1 -5 3 0.0321
2 -1 1 0.0507

_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.1948 2.1187 -3.8285 -0.8401 -0.3999 -0.3666
-2.2378 -0.6831 -1.4240 -0.5975 -0.2852 0.7495
0.5352 15.7091 0.8317 -0.2248 0.9373 -0.2664
0.0734 -15.7199 -1.2078 0.2329 -0.9724 0.0090
-0.0772 5.1975 -3.6513 -0.9349 -0.2241 -0.2752
1.0032 -4.5323 3.2700 0.9668 0.2315 -0.1080
2.2944 -1.3924 1.1873 0.6187 0.1477 -0.7716

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_av_unetI/netI     0.0280
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4195
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.417
_diffrn_reflns_theta_min         3.465
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      103(4)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -29.00  24.00   0.50    0.50    --   45.23 -19.00-120.00  106
  2  ω     30.00  69.00   0.50    1.60    --  102.69 -61.00 -90.00   78
  3  ω     30.00  69.00   0.50    1.60    --  102.69 -61.00  60.00   78
  4  ω     52.00 118.00   0.50    0.50    --   45.23 157.00 -42.00  132
  5  ω     30.00 109.00   0.50    1.60    --  102.69-119.00  77.00  158
  6  ω     30.00 111.00   0.50    1.60    --  102.69-125.00   0.00  162
  7  ω     30.00 133.00   0.50    1.60    --  102.69-157.00 -76.00  206
  8  ω      9.00  90.00   0.50    0.50    --   45.23-119.00  77.00  162
  9  ω    -28.00  30.00   0.50    0.50    --  -45.23  19.00 120.00  116
 10  ω    -90.00  -9.00   0.50    0.50    --  -45.23 119.00 163.00  162
 11  ω   -107.00 -30.00   0.50    1.60    -- -102.69  77.00 150.00  154
 12  ω   -174.00 -90.00   0.50    1.60    -- -102.69 -45.00   0.00  168
 13  ω   -118.00 -64.00   0.50    0.50    --  -45.23 -77.00  30.00  108
 14  ω   -118.00 -51.00   0.50    0.50    --  -45.23-157.00 -76.00  134
 15  ω   -160.00 -51.00   0.50    1.60    -- -102.69-157.00 -76.00  218
 16  ω   -175.00 -86.00   0.50    1.60    -- -102.69 -61.00-180.00  178
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1426410000
_diffrn_orient_matrix_UB_12      -0.0302815000
_diffrn_orient_matrix_UB_13      0.2099296000
_diffrn_orient_matrix_UB_21      0.0261898000
_diffrn_orient_matrix_UB_22      0.0516596000
_diffrn_orient_matrix_UB_23      0.1343650000
_diffrn_orient_matrix_UB_31      -0.3784102000
_diffrn_orient_matrix_UB_32      -0.0078850000
_diffrn_orient_matrix_UB_33      0.0721342000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                972
_reflns_number_total             1152
_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 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.193
_refine_diff_density_min         -0.179
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     82
_refine_ls_number_reflns         1152
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0508
_refine_ls_restrained_S_all      1.107
_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)+(0.0761P)²+0.2045P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1408
_refine_ls_wR_factor_ref         0.1459
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14)
;
_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
N1 N 0.4319(4) 0.30466(6) 0.8267(2) 0.0372(4) Uani 1 1 d . . . . .
C3 C 0.9527(4) 0.48466(7) 0.0697(3) 0.0321(4) Uani 1 1 d . . . . .
C2 C 0.8420(5) 0.44960(7) 0.2236(3) 0.0322(4) Uani 1 1 d . . . . .
C1 C 0.7418(4) 0.41768(7) 0.3556(3) 0.0322(4) Uani 1 1 d . . . . .
C10 C 0.6293(4) 0.37928(7) 0.5115(3) 0.0297(4) Uani 1 1 d . . . . .
C11 C 0.4818(5) 0.39455(7) 0.7117(3) 0.0327(4) Uani 1 1 d . . . . .
H11 H 0.446469 0.430535 0.744819 0.039 Uiso 1 1 calc R U . . .
C12 C 0.3890(5) 0.35590(7) 0.8597(3) 0.0342(5) Uani 1 1 d . . . . .
H12 H 0.287537 0.366571 0.994533 0.041 Uiso 1 1 calc R U . . .
C13 C 0.5705(5) 0.29061(8) 0.6329(3) 0.0378(5) Uani 1 1 d . . . . .
H13 H 0.603351 0.254322 0.605094 0.045 Uiso 1 1 calc R U . . .
C14 C 0.6683(5) 0.32598(7) 0.4715(3) 0.0334(4) Uani 1 1 d . . . . .
H14 H 0.760498 0.314027 0.335614 0.040 Uiso 1 1 calc R U . . .


_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
N1 C12 1.333(2) . ?
N1 C13 1.344(2) . ?
C3 C3 1.210(3) 3_765 ?
C3 C2 1.364(2) . ?
C2 C1 1.208(2) . ?
C1 C10 1.431(2) . ?
C10 C11 1.401(2) . ?
C10 C14 1.390(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.382(2) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C13 C14 1.384(2) . ?
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
C12 N1 C13 116.46(15) . . ?
C3 C3 C2 178.9(3) 3_765 . ?
C1 C2 C3 178.36(19) . . ?
C2 C1 C10 178.87(19) . . ?
C11 C10 C1 120.67(16) . . ?
C14 C10 C1 121.31(15) . . ?
C14 C10 C11 118.01(16) . . ?
C10 C11 H11 120.9 . . ?
C12 C11 C10 118.24(17) . . ?
C12 C11 H11 120.9 . . ?
N1 C12 C11 124.59(16) . . ?
N1 C12 H12 117.7 . . ?
C11 C12 H12 117.7 . . ?
N1 C13 H13 118.1 . . ?
N1 C13 C14 123.77(17) . . ?
C14 C13 H13 118.1 . . ?
C10 C14 H14 120.6 . . ?
C13 C14 C10 118.90(16) . . ?
C13 C14 H14 120.6 . . ?

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
N1 C13 C14 C10 1.4(3) . . . . ?
C1 C10 C11 C12 -177.80(16) . . . . ?
C1 C10 C14 C13 176.94(16) . . . . ?
C10 C11 C12 N1 0.5(3) . . . . ?
C11 C10 C14 C13 -1.9(2) . . . . ?
C12 N1 C13 C14 0.1(3) . . . . ?
C13 N1 C12 C11 -1.1(3) . . . . ?
C14 C10 C11 C12 1.1(2) . . . . ?

_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 1.700
_oxdiff_exptl_absorpt_empirical_full_min 0.697
####################################################################### 
# 
# 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_jp-01-64
_database_code_depnum_ccdc_archive 'CCDC 2244312'
loop_
_audit_author_name
_audit_author_address
'Jarred Potter'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2023-02-24 deposited with the CCDC.	2023-04-06 downloaded from the CCDC.
;
_audit_creation_date             2023-01-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H22 S2'
_chemical_formula_sum            'C28 H22 S2'
_chemical_formula_weight         422.57
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C26 H10 S2'
_chemical_oxdiff_usercomment     'Marcus for Jarred'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
S S 0.3331 0.5567 '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                   7.3018(3)
_cell_length_b                   8.2369(3)
_cell_length_c                   19.0284(7)
_cell_angle_alpha                90
_cell_angle_beta                 100.137(4)
_cell_angle_gamma                90
_cell_volume                     1126.58(8)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5563
_cell_measurement_temperature    111(16)
_cell_measurement_theta_max      74.7650
_cell_measurement_theta_min      4.7010
_shelx_estimated_absorpt_T_max   0.917
_shelx_estimated_absorpt_T_min   0.705
_exptl_absorpt_coefficient_mu    2.214
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.770
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             444
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 0 1 0.0308
0 5 1 0.0522
5 0 -2 0.0563
2 -5 -2 0.0874
0 -5 -1 0.1018
1 1 11 0.0119
-1 -1 -12 0.0232

_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-2.0015 0.0060 1.0113 0.0548 -0.3416 -0.2422
-0.1610 5.3173 1.2825 0.0793 -0.5990 0.7968
4.7390 0.0978 -2.0754 -0.1042 0.7986 0.5927
2.2827 -4.6656 -2.0731 -0.1173 0.8912 -0.4381
-0.4849 -5.2916 -0.9907 -0.0645 0.4860 -0.8716
0.8604 0.9065 11.3794 0.9378 0.1232 0.3247
-0.6587 -0.5758 -11.6644 -0.9597 -0.1260 -0.2512

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_av_unetI/netI     0.0226
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.932
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8490
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.932
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.033
_diffrn_reflns_theta_min         4.722
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      111(16)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.975
_diffrn_measured_fraction_theta_max 0.932
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -118.00 -33.00   0.50    1.50    --  -46.23 -47.00  12.00  170
  2  ω    -55.00  26.00   0.50    1.50    --  -46.23  47.00 160.00  162
  3  ω     33.00 118.00   0.50    1.50    --   46.23  47.00 160.00  170
  4  ω    -25.00  51.00   0.50    1.50    --   46.23 -47.00  12.00  152
  5  ω   -176.00 -91.00   0.50    8.00    -- -103.63 -47.00  12.00  170
  6  ω     91.00 176.00   0.50    8.00    --  103.63  47.00 160.00  170
  7  ω   -118.00 -73.00   0.50    1.50    --  -46.23-125.00 120.00   90
  8  ω    -27.00  26.00   0.50    1.50    --  -46.23  19.00-120.00  106
  9  ω   -118.00 -82.00   0.50    1.50    --  -46.23-125.00 150.00   72
 10  ω    -67.00 -41.00   0.50    8.00    -- -103.63  61.00 -30.00   52
 11  ω   -122.00 -84.00   0.50    8.00    -- -103.63 -77.00 120.00   76
 12  ω    -82.00 -52.00   0.50    8.00    -- -103.63  77.00  60.00   60
 13  ω    -73.00 -32.00   0.50    8.00    -- -103.63  61.00   0.00   82
 14  ω   -175.00-128.00   0.50    8.00    -- -103.63 -77.00 120.00   94
 15  ω    -72.00 -32.00   0.50    8.00    -- -103.63  61.00-180.00   80
 16  ω     31.00  68.00   0.50    8.00    --  103.63 -61.00   0.00   74
 17  ω     51.00  94.00   0.50    8.00    --  103.63 -94.00 120.00   86
 18  ω     89.00 174.00   0.50    8.00    --  103.63  61.00-120.00  170
 19  ω     32.00  58.00   0.50    8.00    --  103.63 -61.00-120.00   52
 20  ω     80.00 107.00   0.50    8.00    --  103.63-125.00-120.00   54
 21  ω     31.00  74.00   0.50    8.00    --  103.63-125.00-120.00   86
 22  ω     34.00  69.00   0.50    8.00    --  103.63 -61.00  30.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0138859000
_diffrn_orient_matrix_UB_12      -0.0043812000
_diffrn_orient_matrix_UB_13      0.0817092000
_diffrn_orient_matrix_UB_21      0.1735689000
_diffrn_orient_matrix_UB_22      -0.1089389000
_diffrn_orient_matrix_UB_23      0.0063797000
_diffrn_orient_matrix_UB_31      0.1249914000
_diffrn_orient_matrix_UB_32      0.1519539000
_diffrn_orient_matrix_UB_33      0.0069733000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2024
_reflns_number_total             2195
_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 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.862
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.092
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2195
_refine_ls_number_restraints     14
_refine_ls_R_factor_all          0.0720
_refine_ls_R_factor_gt           0.0690
_refine_ls_restrained_S_all      1.084
_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)+(0.1034P)²+2.0295P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1974
_refine_ls_wR_factor_ref         0.1995
_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
 S1-C13 \\sim S1A-C13
 with sigma of 0.02
 C19A-C17A \\sim C19-C17
 with sigma of 0.02
 S1-C16 \\sim S1A-C16A
 with sigma of 0.02
 C18-C19 \\sim C18A-C19A
 with sigma of 0.04
 C16A-C17A \\sim C16-C17
 with sigma of 0.02
 C17-C18 \\sim C17A-C18A
 with sigma of 0.02
 C17-C19 \\sim C17A-C19A
 with sigma of 0.02
 S1A-C16A \\sim S1-C16
 with sigma of 0.02
 C17-C16 \\sim C17A-C16A
 with sigma of 0.02
 C18-C16 \\sim C18A-C16A
 with sigma of 0.04
 C19-C16 \\sim C19A-C16A
 with sigma of 0.04
 S1-C17 \\sim S1A-C17A
 with sigma of 0.04
 C14-C17 \\sim C14-C17A
 with sigma of 0.02
 S1A-C13 \\sim S1-C13
 with sigma of 0.02
 C14-C18 \\sim C14-C18A
 with sigma of 0.04
 C18A-C17A \\sim C18-C17
 with sigma of 0.02
 C14-C19 \\sim C14-C19A
 with sigma of 0.04
 C14-C16 \\sim C14-C16A
 with sigma of 0.04
 C13-C16 \\sim C13-C16A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C19A) = Uanis(C19)
Uanis(C16A) = Uanis(C16)
Uanis(S1A) = Uanis(S1)
Uanis(C17A) = Uanis(C17)
Uanis(C18A) = Uanis(C18)
4. Others
 Sof(S1A)=Sof(C16A)=Sof(H16C)=Sof(H16D)=Sof(C17A)=Sof(C19A)=Sof(H19D)=
 Sof(H19E)=Sof(H19F)=Sof(C18A)=Sof(H18D)=Sof(H18E)=Sof(H18F)=1-FVAR(1)
 Sof(S1)=Sof(C17)=Sof(C18)=Sof(H18A)=Sof(H18B)=Sof(H18C)=Sof(C19)=Sof(H19A)=
 Sof(H19B)=Sof(H19C)=Sof(C16)=Sof(H16A)=Sof(H16B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C16A(H16C,H16D)
5.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C15(H15), C12(H12)
5.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C19(H19A,H19B,H19C), C19A(H19D,H19E,H19F), C18A(H18D,
 H18E,H18F)
;
_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 -0.1247(4) 0.2322(3) 0.33701(15) 0.0356(5) Uani 0.845(6) 1 d D . P A 1
C14 C 0.2208(4) 0.3369(4) 0.34579(16) 0.0316(7) Uani 1 1 d D . . . .
C3 C 0.7917(4) 0.8637(4) 0.47234(17) 0.0345(7) Uani 1 1 d . . . . .
C13 C 0.0534(4) 0.3714(4) 0.36859(16) 0.0308(6) Uani 1 1 d D . . . .
C11 C 0.1884(5) 0.6022(4) 0.43392(17) 0.0351(7) Uani 1 1 d . . . . .
H11 H 0.177544 0.693908 0.463200 0.042 Uiso 1 1 calc R U . . .
C10 C 0.3573(4) 0.5701(4) 0.41222(17) 0.0317(7) Uani 1 1 d . . . . .
C4 C 0.9249(4) 0.9509(4) 0.48996(17) 0.0341(7) Uani 1 1 d . . . . .
C15 C 0.3723(4) 0.4367(4) 0.36738(17) 0.0338(7) Uani 1 1 d . . . . .
H15 H 0.486751 0.415313 0.351927 0.041 Uiso 1 1 calc R U . . .
C2 C 0.6436(5) 0.7629(4) 0.45274(17) 0.0331(7) Uani 1 1 d . . . . .
C12 C 0.0363(4) 0.5020(4) 0.41324(17) 0.0356(7) Uani 1 1 d . . . . .
H12 H -0.077655 0.522056 0.429287 0.043 Uiso 1 1 calc R U . . .
C1 C 0.5123(5) 0.6745(4) 0.43401(17) 0.0335(7) Uani 1 1 d . . . . .
C17 C 0.2152(6) 0.1889(5) 0.2969(2) 0.0346(10) Uani 0.845(6) 1 d D . P A 1
C18 C 0.3168(7) 0.2145(6) 0.2346(2) 0.0395(10) Uani 0.845(6) 1 d D . P A 1
H18A H 0.265729 0.310007 0.207233 0.059 Uiso 0.845(6) 1 calc R U P A 1
H18B H 0.300585 0.118608 0.203630 0.059 Uiso 0.845(6) 1 calc R U P A 1
H18C H 0.449563 0.231398 0.252712 0.059 Uiso 0.845(6) 1 calc R U P A 1
C19 C 0.3038(8) 0.0454(5) 0.3430(2) 0.0427(11) Uani 0.845(6) 1 d D . P A 1
H19A H 0.429714 0.075022 0.366427 0.064 Uiso 0.845(6) 1 calc R U P A 1
H19B H 0.309688 -0.049651 0.312439 0.064 Uiso 0.845(6) 1 calc R U P A 1
H19C H 0.228101 0.019580 0.379215 0.064 Uiso 0.845(6) 1 calc R U P A 1
C16 C 0.0066(6) 0.1583(5) 0.2696(2) 0.0413(10) Uani 0.845(6) 1 d D . P A 1
H16A H -0.016116 0.040816 0.261317 0.050 Uiso 0.845(6) 1 calc R U P A 1
H16B H -0.033812 0.216224 0.223935 0.050 Uiso 0.845(6) 1 calc R U P A 1
S1A S -0.130(2) 0.249(2) 0.3260(10) 0.0356(5) Uani 0.155(6) 1 d D . P A 2
C16A C 0.037(2) 0.088(2) 0.3168(12) 0.0413(10) Uani 0.155(6) 1 d D . P A 2
H16C H 0.052234 0.015303 0.358814 0.050 Uiso 0.155(6) 1 calc R U P A 2
H16D H -0.008458 0.022596 0.273543 0.050 Uiso 0.155(6) 1 calc R U P A 2
C17A C 0.224(3) 0.169(2) 0.3108(12) 0.0346(10) Uani 0.155(6) 1 d D . P A 2
C19A C 0.390(3) 0.062(3) 0.3424(14) 0.0427(11) Uani 0.155(6) 1 d D . P A 2
H19D H 0.505863 0.118062 0.337637 0.064 Uiso 0.155(6) 1 calc R U P A 2
H19E H 0.382877 -0.041310 0.316855 0.064 Uiso 0.155(6) 1 calc R U P A 2
H19F H 0.387831 0.042519 0.393038 0.064 Uiso 0.155(6) 1 calc R U P A 2
C18A C 0.231(4) 0.210(3) 0.2331(11) 0.0395(10) Uani 0.155(6) 1 d D . P A 2
H18D H 0.110043 0.252629 0.209976 0.059 Uiso 0.155(6) 1 calc R U P A 2
H18E H 0.260799 0.112411 0.208066 0.059 Uiso 0.155(6) 1 calc R U P A 2
H18F H 0.327164 0.292645 0.231466 0.059 Uiso 0.155(6) 1 calc R U P A 2


_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 C13 1.758(4) . ?
S1 C16 1.835(5) . ?
C14 C13 1.397(4) . ?
C14 C15 1.382(4) . ?
C14 C17 1.529(5) . ?
C14 C17A 1.541(17) . ?
C3 C4 1.208(5) . ?
C3 C2 1.362(5) . ?
C13 C12 1.390(5) . ?
C13 S1A 1.757(15) . ?
C11 H11 0.9500 . ?
C11 C10 1.393(4) . ?
C11 C12 1.385(5) . ?
C10 C15 1.407(5) . ?
C10 C1 1.424(4) . ?
C4 C4 1.362(6) 3_776 ?
C15 H15 0.9500 . ?
C2 C1 1.207(5) . ?
C12 H12 0.9500 . ?
C17 C18 1.521(6) . ?
C17 C19 1.544(6) . ?
C17 C16 1.541(6) . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
S1A C16A 1.828(17) . ?
C16A H16C 0.9900 . ?
C16A H16D 0.9900 . ?
C16A C17A 1.542(17) . ?
C17A C19A 1.529(17) . ?
C17A C18A 1.527(18) . ?
C19A H19D 0.9800 . ?
C19A H19E 0.9800 . ?
C19A H19F 0.9800 . ?
C18A H18D 0.9800 . ?
C18A H18E 0.9800 . ?
C18A H18F 0.9800 . ?

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
C13 S1 C16 90.5(2) . . ?
C13 C14 C17 114.8(3) . . ?
C13 C14 C17A 113.5(8) . . ?
C15 C14 C13 119.0(3) . . ?
C15 C14 C17 126.1(3) . . ?
C15 C14 C17A 126.3(8) . . ?
C4 C3 C2 178.9(4) . . ?
C14 C13 S1 113.3(3) . . ?
C14 C13 S1A 112.2(7) . . ?
C12 C13 S1 125.0(3) . . ?
C12 C13 C14 121.7(3) . . ?
C12 C13 S1A 125.7(7) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C12 C11 C10 120.7(3) . . ?
C11 C10 C15 119.7(3) . . ?
C11 C10 C1 119.9(3) . . ?
C15 C10 C1 120.4(3) . . ?
C3 C4 C4 179.8(5) . 3_776 ?
C14 C15 C10 120.1(3) . . ?
C14 C15 H15 120.0 . . ?
C10 C15 H15 120.0 . . ?
C1 C2 C3 178.7(4) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 C13 118.8(3) . . ?
C11 C12 H12 120.6 . . ?
C2 C1 C10 179.8(4) . . ?
C14 C17 C19 107.6(3) . . ?
C14 C17 C16 104.8(3) . . ?
C18 C17 C14 113.5(3) . . ?
C18 C17 C19 109.6(4) . . ?
C18 C17 C16 110.4(4) . . ?
C16 C17 C19 110.9(4) . . ?
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 . . ?
C17 C19 H19A 109.5 . . ?
C17 C19 H19B 109.5 . . ?
C17 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
S1 C16 H16A 110.0 . . ?
S1 C16 H16B 110.0 . . ?
C17 C16 S1 108.5(3) . . ?
C17 C16 H16A 110.0 . . ?
C17 C16 H16B 110.0 . . ?
H16A C16 H16B 108.4 . . ?
C13 S1A C16A 89.7(9) . . ?
S1A C16A H16C 110.1 . . ?
S1A C16A H16D 110.1 . . ?
H16C C16A H16D 108.4 . . ?
C17A C16A S1A 108.1(12) . . ?
C17A C16A H16C 110.1 . . ?
C17A C16A H16D 110.1 . . ?
C14 C17A C16A 105.9(12) . . ?
C19A C17A C14 114.6(16) . . ?
C19A C17A C16A 112.2(17) . . ?
C18A C17A C14 102.8(15) . . ?
C18A C17A C16A 110.5(17) . . ?
C18A C17A C19A 110.5(17) . . ?
C17A C19A H19D 109.5 . . ?
C17A C19A H19E 109.5 . . ?
C17A C19A H19F 109.5 . . ?
H19D C19A H19E 109.5 . . ?
H19D C19A H19F 109.5 . . ?
H19E C19A H19F 109.5 . . ?
C17A C18A H18D 109.5 . . ?
C17A C18A H18E 109.5 . . ?
C17A C18A H18F 109.5 . . ?
H18D C18A H18E 109.5 . . ?
H18D C18A H18F 109.5 . . ?
H18E C18A H18F 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 C13 C12 C11 -179.9(3) . . . . ?
C14 C13 C12 C11 1.7(5) . . . . ?
C14 C13 S1A C16A 29.1(12) . . . . ?
C14 C17 C16 S1 -28.2(4) . . . . ?
C13 S1 C16 C17 26.0(3) . . . . ?
C13 C14 C15 C10 0.6(5) . . . . ?
C13 C14 C17 C18 138.2(4) . . . . ?
C13 C14 C17 C19 -100.3(4) . . . . ?
C13 C14 C17 C16 17.7(4) . . . . ?
C13 C14 C17A C16A -3.1(17) . . . . ?
C13 C14 C17A C19A -127.3(15) . . . . ?
C13 C14 C17A C18A 112.8(14) . . . . ?
C13 S1A C16A C17A -29.8(16) . . . . ?
C11 C10 C15 C14 -0.9(5) . . . . ?
C10 C11 C12 C13 -2.0(5) . . . . ?
C15 C14 C13 S1 -179.6(3) . . . . ?
C15 C14 C13 C12 -1.0(5) . . . . ?
C15 C14 C13 S1A 171.8(7) . . . . ?
C15 C14 C17 C18 -40.8(5) . . . . ?
C15 C14 C17 C19 80.7(5) . . . . ?
C15 C14 C17 C16 -161.3(3) . . . . ?
C15 C14 C17A C16A 164.2(10) . . . . ?
C15 C14 C17A C19A 40(2) . . . . ?
C15 C14 C17A C18A -79.8(17) . . . . ?
C12 C13 S1A C16A -158.5(8) . . . . ?
C12 C11 C10 C15 1.6(5) . . . . ?
C12 C11 C10 C1 180.0(3) . . . . ?
C1 C10 C15 C14 -179.3(3) . . . . ?
C17 C14 C13 S1 1.4(4) . . . . ?
C17 C14 C13 C12 180.0(3) . . . . ?
C17 C14 C15 C10 179.5(3) . . . . ?
C18 C17 C16 S1 -150.7(3) . . . . ?
C19 C17 C16 S1 87.6(4) . . . . ?
C16 S1 C13 C14 -16.1(3) . . . . ?
C16 S1 C13 C12 165.3(3) . . . . ?
S1A C13 C12 C11 -170.1(8) . . . . ?
S1A C16A C17A C14 23.3(19) . . . . ?
S1A C16A C17A C19A 149.0(17) . . . . ?
S1A C16A C17A C18A -87.3(19) . . . . ?
C17A C14 C13 C12 167.4(10) . . . . ?
C17A C14 C13 S1A -19.9(13) . . . . ?
C17A C14 C15 C10 -166.1(12) . . . . ?

_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 1.297
_oxdiff_exptl_absorpt_empirical_full_min 0.835
####################################################################### 
# 
# 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_jp-01-45
_database_code_depnum_ccdc_archive 'CCDC 2244314'
loop_
_audit_author_name
_audit_author_address
'Jarred Potter'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2023-02-24 deposited with the CCDC.	2023-04-06 downloaded from the CCDC.
;
_audit_creation_date             2023-01-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H13 N O'
_chemical_formula_sum            'C13 H13 N O'
_chemical_formula_weight         199.24
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N2'
_chemical_oxdiff_usercomment     'Marcus for Jarred'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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.
;
_vrf_PLAT420_jp-01-45            
;
PROBLEM: D-H Bond Without Acceptor  O1       --H1       .     Please Check 
RESPONSE: The O-H donor forms an O-H to pi interaction with an adjacent molecule.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 1 2/a 1'
_space_group_name_Hall           '-I 2ya'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   16.2725(2)
_cell_length_b                   5.97010(10)
_cell_length_c                   23.8665(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.1140(10)
_cell_angle_gamma                90
_cell_volume                     2258.13(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    8973
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      75.0800
_cell_measurement_theta_min      3.7830
_shelx_estimated_absorpt_T_max   0.960
_shelx_estimated_absorpt_T_min   0.691
_exptl_absorpt_coefficient_mu    0.586
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.336
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear intense colourless'
_exptl_crystal_density_diffrn    1.172
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             848
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 0 1 0.0343
0 -1 2 0.2969
-2 3 -6 0.2742
-3 0 15 0.0235
3 0 -15 0.0311
9 0 5 0.0428
-9 0 -5 0.0333

_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.07
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-0.9989 -0.0000 1.0005 -0.0280 0.0993 -0.0163
0.0034 -0.9995 1.9970 0.0039 0.0124 -0.2896
-1.5372 3.4619 -5.9118 -0.0257 0.1043 0.9942
-3.2556 -0.1951 15.4144 -0.7749 0.4217 -0.4708
3.3915 -0.0424 -15.4139 0.7993 -0.4349 0.4146
9.1368 0.0751 4.5290 -0.5484 -0.7966 -0.2543
-9.0972 -0.0045 -4.6447 0.5455 0.7923 0.2734

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            12608
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.288
_diffrn_reflns_theta_min         3.803
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -42.00  27.00   0.50    0.15    --  -46.32  37.00  76.00  138
  2  ω   -119.00 -34.00   0.50    0.15    --  -46.32 -37.00 -79.00  170
  3  ω    -27.00  42.00   0.50    0.15    --   46.32 -37.00 -79.00  138
  4  ω     34.00 120.00   0.50    0.15    --   46.32  37.00  76.00  172
  5  ω   -175.00 -90.00   0.50    0.80    -- -102.29 -37.00 -79.00  170
  6  ω    -26.00  29.00   0.50    0.15    --  -46.32  19.00-120.00  110
  7  ω    -28.00  26.00   0.50    0.15    --   46.32 -19.00 120.00  108
  8  ω   -105.00 -30.00   0.50    0.80    -- -102.29  77.00 -60.00  150
  9  ω    -71.00 -30.00   0.50    0.80    -- -102.29  61.00-150.00   82
 10  ω   -105.00 -30.00   0.50    0.80    -- -102.29  77.00-120.00  150
 11  ω     30.00  71.00   0.50    0.80    --  102.29 -61.00  60.00   82
 12  ω     30.00  71.00   0.50    0.80    --  102.29 -61.00 120.00   82
 13  ω     30.00 105.00   0.50    0.80    --  102.29 -94.00  30.00  150
 14  ω     30.00  71.00   0.50    0.80    --  102.29 -61.00 -60.00   82
 15  ω     30.00  71.00   0.50    0.80    --  102.29 -61.00   0.00   82
 16  ω     30.00  71.00   0.50    0.80    --  102.29 -61.00 -30.00   82
 17  ω     30.00 105.00   0.50    0.80    --  102.29 -77.00 -60.00  150
 18  ω     30.00  71.00   0.50    0.80    --  102.29 -61.00  30.00   82
 19  ω     30.00  71.00   0.50    0.80    --  102.29 -61.00 150.00   82
 20  ω     30.00  71.00   0.50    0.80    --  102.29 -61.00  90.00   82
 21  ω     90.00 176.00   0.50    0.80    --  102.29  37.00  76.00  172
 22  ω     32.00 118.00   0.50    0.15    --   46.32  57.00 120.00  172
 23  ω     24.00 112.00   0.50    0.15    --   46.32  77.00-120.00  176
 24  ω     32.00 118.00   0.50    0.15    --   46.32  57.00-180.00  172
 25  ω   -149.00-122.00   0.50    0.80    -- -102.29 -85.00 112.00   54
 26  ω     27.00  61.00   0.50    0.15    --   46.32 -57.00 150.00   68
 27  ω   -120.00 -94.00   0.50    0.80    -- -102.29 141.00 -97.28   52
 28  ω   -166.00-111.00   0.50    0.80    -- -102.29 -61.00   0.00  110
 29  ω    -76.00 -39.00   0.50    0.80    -- -102.29 125.00  90.00   74
 30  ω    -71.00 -46.00   0.50    0.80    -- -102.29  61.00 -60.00   50
 31  ω   -107.00 -96.50   0.50    0.80    -- -102.29 -85.00 112.00   21
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0301984000
_diffrn_orient_matrix_UB_12      -0.1201844000
_diffrn_orient_matrix_UB_13      -0.0581725000
_diffrn_orient_matrix_UB_21      -0.0912452000
_diffrn_orient_matrix_UB_22      0.0034900000
_diffrn_orient_matrix_UB_23      0.0081310000
_diffrn_orient_matrix_UB_31      -0.0144862000
_diffrn_orient_matrix_UB_32      0.2283072000
_diffrn_orient_matrix_UB_33      -0.0307117000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2116
_reflns_number_total             2276
_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 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.202
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0360
_refine_ls_R_factor_gt           0.0342
_refine_ls_restrained_S_all      1.070
_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)+(0.0454P)²+1.1592P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.0920
_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, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C15(H15), C14(H14), C12(H12), C11(H11)
2.b Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C31(H31A,H31B,H31C)
2.c Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   mixed
_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
O1 O 0.42366(4) 0.22983(12) 0.65388(3) 0.02278(18) Uani 1 1 d . . . . .
H1 H 0.459781 0.154395 0.641936 0.034 Uiso 1 1 calc R U . . .
N1 N 0.44735(7) 1.37688(16) 0.27971(4) 0.0314(2) Uani 1 1 d . . . . .
C4 C 0.35658(6) 0.36540(16) 0.56116(4) 0.0204(2) Uani 1 1 d . . . . .
C3 C 0.36612(6) 0.48051(16) 0.52179(4) 0.0205(2) Uani 1 1 d . . . . .
C2 C 0.37812(6) 0.62145(16) 0.47879(4) 0.0207(2) Uani 1 1 d . . . . .
C1 C 0.38878(6) 0.74982(16) 0.44208(4) 0.0208(2) Uani 1 1 d . . . . .
C10 C 0.40259(6) 0.90737(16) 0.40013(4) 0.0190(2) Uani 1 1 d . . . . .
C15 C 0.37586(6) 0.86576(16) 0.34079(4) 0.0204(2) Uani 1 1 d . . . . .
H15 H 0.347248 0.730024 0.327961 0.025 Uiso 1 1 calc R U . . .
C14 C 0.39056(6) 1.01922(16) 0.30088(4) 0.0210(2) Uani 1 1 d . . . . .
H14 H 0.372087 0.987412 0.260999 0.025 Uiso 1 1 calc R U . . .
C13 C 0.43260(6) 1.22241(16) 0.31855(4) 0.0207(2) Uani 1 1 d . . . . .
C12 C 0.45859(6) 1.26426(16) 0.37788(4) 0.0213(2) Uani 1 1 d . . . . .
H12 H 0.486794 1.400434 0.390809 0.026 Uiso 1 1 calc R U . . .
C11 C 0.44381(6) 1.11088(16) 0.41758(4) 0.0208(2) Uani 1 1 d . . . . .
H11 H 0.461799 1.143328 0.457456 0.025 Uiso 1 1 calc R U . . .
C30 C 0.34507(6) 0.23075(16) 0.61070(4) 0.0194(2) Uani 1 1 d . . . . .
C32 C 0.28092(6) 0.34100(18) 0.63947(4) 0.0240(2) Uani 1 1 d . . . . .
H32A H 0.275254 0.252005 0.672890 0.036 Uiso 1 1 calc R U . . .
H32B H 0.226181 0.349592 0.612022 0.036 Uiso 1 1 calc R U . . .
H32C H 0.300048 0.492329 0.652004 0.036 Uiso 1 1 calc R U . . .
C31 C 0.31968(7) -0.00778(17) 0.59180(5) 0.0290(2) Uani 1 1 d . . . . .
H31A H 0.363504 -0.075586 0.575095 0.043 Uiso 1 1 calc R U . . .
H31B H 0.266137 -0.005523 0.562988 0.043 Uiso 1 1 calc R U . . .
H31C H 0.313060 -0.095800 0.625159 0.043 Uiso 1 1 calc R U . . .
H1A H 0.4361(9) 1.343(2) 0.2423(7) 0.040(4) Uiso 1 1 d . . . . .
H1B H 0.4827(9) 1.491(2) 0.2944(6) 0.039(4) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.8400 . ?
O1 C30 1.4489(11) . ?
N1 C13 1.3668(13) . ?
N1 H1A 0.893(15) . ?
N1 H1B 0.911(15) . ?
C4 C3 1.2021(14) . ?
C4 C30 1.4765(13) . ?
C3 C2 1.3750(13) . ?
C2 C1 1.2057(14) . ?
C1 C10 1.4282(13) . ?
C10 C15 1.4061(13) . ?
C10 C11 1.4045(14) . ?
C15 H15 0.9500 . ?
C15 C14 1.3811(13) . ?
C14 H14 0.9500 . ?
C14 C13 1.4094(14) . ?
C13 C12 1.4053(14) . ?
C12 H12 0.9500 . ?
C12 C11 1.3776(14) . ?
C11 H11 0.9500 . ?
C30 C32 1.5229(13) . ?
C30 C31 1.5224(13) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?

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
C30 O1 H1 109.5 . . ?
C13 N1 H1A 119.7(10) . . ?
C13 N1 H1B 116.0(9) . . ?
H1A N1 H1B 121.7(13) . . ?
C3 C4 C30 178.10(10) . . ?
C4 C3 C2 176.96(10) . . ?
C1 C2 C3 178.24(10) . . ?
C2 C1 C10 178.01(10) . . ?
C15 C10 C1 121.86(9) . . ?
C11 C10 C1 120.16(8) . . ?
C11 C10 C15 117.99(9) . . ?
C10 C15 H15 119.5 . . ?
C14 C15 C10 121.00(9) . . ?
C14 C15 H15 119.5 . . ?
C15 C14 H14 119.6 . . ?
C15 C14 C13 120.86(8) . . ?
C13 C14 H14 119.6 . . ?
N1 C13 C14 121.72(9) . . ?
N1 C13 C12 120.29(9) . . ?
C12 C13 C14 117.98(9) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 C13 121.02(9) . . ?
C11 C12 H12 119.5 . . ?
C10 C11 H11 119.4 . . ?
C12 C11 C10 121.15(9) . . ?
C12 C11 H11 119.4 . . ?
O1 C30 C4 108.65(7) . . ?
O1 C30 C32 105.41(7) . . ?
O1 C30 C31 110.09(8) . . ?
C4 C30 C32 110.50(8) . . ?
C4 C30 C31 110.32(8) . . ?
C31 C30 C32 111.73(8) . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 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
N1 C13 C12 C11 179.64(9) . . . . ?
C1 C10 C15 C14 -179.34(9) . . . . ?
C1 C10 C11 C12 179.31(8) . . . . ?
C10 C15 C14 C13 -0.19(14) . . . . ?
C15 C10 C11 C12 -0.77(14) . . . . ?
C15 C14 C13 N1 -179.66(9) . . . . ?
C15 C14 C13 C12 -0.34(14) . . . . ?
C14 C13 C12 C11 0.32(14) . . . . ?
C13 C12 C11 C10 0.24(14) . . . . ?
C11 C10 C15 C14 0.74(14) . . . . ?

_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 1.424
_oxdiff_exptl_absorpt_empirical_full_min 0.572
####################################################################### 
# 
# 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_jp-01-55_auto
_database_code_depnum_ccdc_archive 'CCDC 2244313'
loop_
_audit_author_name
_audit_author_address
'Jarred Potter'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2023-02-24 deposited with the CCDC.	2023-04-06 downloaded from the CCDC.
;
_audit_creation_date             2023-01-20
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H12 N2'
_chemical_formula_sum            'C20 H12 N2'
_chemical_formula_weight         280.32
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 S2'
_chemical_oxdiff_usercomment     'Marcus for Jarred'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 '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           29
_space_group_name_H-M_alt        'P c a 21'
_space_group_name_Hall           'P 2c -2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, z+1/2'

_cell_length_a                   7.8557(3)
_cell_length_b                   9.7053(3)
_cell_length_c                   38.6997(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2950.54(16)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5764
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      73.7020
_cell_measurement_theta_min      4.5740
_shelx_estimated_absorpt_T_max   0.970
_shelx_estimated_absorpt_T_min   0.877
_exptl_absorpt_coefficient_mu    0.583
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.43343
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.104a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1168
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.074
_exptl_crystal_size_min          0.053
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0473
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.955
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -48
_diffrn_reflns_number            11859
_diffrn_reflns_point_group_measured_fraction_full 0.666
_diffrn_reflns_point_group_measured_fraction_max 0.633
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.438
_diffrn_reflns_theta_min         4.556
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.955
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -5.00  22.00   0.50    0.30    --   46.23 -19.00-180.00   54
  2  ω     37.00  68.00   0.50    3.00    --  102.69 -61.00 -90.00   62
  3  ω      4.00  40.00   0.50    0.30    --   46.23 -37.00 150.00   72
  4  ω     31.00  75.00   0.50    3.00    --  102.69 -77.00 150.00   88
  5  ω     41.00  88.00   0.50    3.00    --  102.69 -77.00 120.00   94
  6  ω     22.00 104.00   0.50    0.30    --   46.23-142.00  50.00  164
  7  ω   -114.00 -30.00   0.50    3.00    -- -102.69 128.00 -64.00  168
  8  ω    -66.00 -30.00   0.50    3.00    -- -102.69  61.00  60.00   72
  9  ω     76.00 102.00   0.50    3.00    --  102.69 -94.00-180.00   52
 10  ω   -108.00 -75.00   0.50    0.30    --  -46.23-125.00-180.00   66
 11  ω   -115.00 -73.00   0.50    0.30    --  -46.23-125.00 -90.00   84
 12  ω   -141.00 -90.00   0.50    3.00    -- -102.69 -22.00 -85.00  102
 13  ω   -174.00 -96.00   0.50    3.00    -- -102.69-103.00 116.00  156
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1486331000
_diffrn_orient_matrix_UB_12      0.0392147000
_diffrn_orient_matrix_UB_13      -0.0113745000
_diffrn_orient_matrix_UB_21      -0.0325499000
_diffrn_orient_matrix_UB_22      0.1920061000
_diffrn_orient_matrix_UB_23      0.0005351000
_diffrn_orient_matrix_UB_31      0.0448563000
_diffrn_orient_matrix_UB_32      0.0091252000
_diffrn_orient_matrix_UB_33      0.0381565000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.304
_reflns_Friedel_fraction_full    0.324
_reflns_Friedel_fraction_max     0.300
_reflns_number_gt                3553
_reflns_number_total             3862
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.104a (Rigaku OD, 2021)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.4(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     494
_refine_ls_number_reflns         3862
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0407
_refine_ls_restrained_S_all      1.057
_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)+(0.0713P)²+0.3589P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1097
_refine_ls_wR_factor_ref         0.1136
_refine_special_details          'Refined as a 2-component inversion twin.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1.4(10)
 -0.4(10)
;
_atom_sites_solution_hydrogens   difmap
_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
N1 N 1.4444(3) 0.0666(3) 0.13488(7) 0.0293(5) Uani 1 1 d . . . . .
H1A H 1.509(6) -0.005(4) 0.1274(12) 0.034(10) Uiso 1 1 d . . . . .
H1B H 1.506(5) 0.139(4) 0.1317(10) 0.033(9) Uiso 1 1 d . . . . .
N2 N 0.3849(3) 0.2001(3) 0.60592(7) 0.0294(5) Uani 1 1 d . . . . .
H2A H 0.417(7) 0.283(6) 0.6125(15) 0.076(16) Uiso 1 1 d . . . . .
H2B H 0.284(6) 0.164(4) 0.6100(11) 0.044(10) Uiso 1 1 d . . . . .
C4 C 0.9036(4) 0.0534(3) 0.35140(7) 0.0276(6) Uani 1 1 d . . . . .
C3 C 0.9737(4) 0.0407(3) 0.32360(7) 0.0271(5) Uani 1 1 d . . . . .
C2 C 1.0516(4) 0.0320(3) 0.29239(8) 0.0273(6) Uani 1 1 d . . . . .
C1 C 1.1222(4) 0.0289(3) 0.26435(7) 0.0262(6) Uani 1 1 d . . . . .
C10 C 1.2045(4) 0.0356(3) 0.23161(7) 0.0263(5) Uani 1 1 d . . . . .
C15 C 1.2511(4) -0.0830(3) 0.21341(8) 0.0281(5) Uani 1 1 d . . . . .
H15 H 1.223(5) -0.165(4) 0.2233(10) 0.036(9) Uiso 1 1 d . . . . .
C14 C 1.3319(4) -0.0723(3) 0.18165(7) 0.0272(6) Uani 1 1 d . . . . .
H14 H 1.367(4) -0.157(4) 0.1706(9) 0.030(8) Uiso 1 1 d . . . . .
C13 C 1.3693(3) 0.0562(3) 0.16754(7) 0.0253(5) Uani 1 1 d . . . . .
C12 C 1.3234(3) 0.1747(3) 0.18569(7) 0.0277(5) Uani 1 1 d . . . . .
H12 H 1.348(4) 0.265(3) 0.1774(8) 0.017(7) Uiso 1 1 d . . . . .
C11 C 1.2404(3) 0.1651(3) 0.21699(7) 0.0271(5) Uani 1 1 d . . . . .
H11 H 1.202(4) 0.254(4) 0.2297(9) 0.029(8) Uiso 1 1 d . . . . .
C5 C 0.8249(3) 0.0723(3) 0.38222(7) 0.0272(5) Uani 1 1 d . . . . .
C6 C 0.7559(4) 0.0920(3) 0.41011(7) 0.0275(5) Uani 1 1 d . . . . .
C7 C 0.6842(3) 0.1137(3) 0.44141(7) 0.0269(5) Uani 1 1 d . . . . .
C8 C 0.6233(3) 0.1310(3) 0.47003(7) 0.0264(5) Uani 1 1 d . . . . .
C20 C 0.5616(3) 0.1483(3) 0.50436(7) 0.0254(5) Uani 1 1 d . . . . .
C25 C 0.4259(3) 0.0703(3) 0.51681(7) 0.0271(6) Uani 1 1 d . . . . .
H25 H 0.369(6) 0.005(4) 0.5013(13) 0.042(11) Uiso 1 1 d . . . . .
C24 C 0.3657(3) 0.0876(3) 0.55021(7) 0.0272(5) Uani 1 1 d . . . . .
H24 H 0.271(5) 0.032(4) 0.5566(10) 0.028(8) Uiso 1 1 d . . . . .
C23 C 0.4417(3) 0.1853(3) 0.57199(7) 0.0258(5) Uani 1 1 d . . . . .
C22 C 0.5782(4) 0.2619(3) 0.55974(7) 0.0279(5) Uani 1 1 d . . . . .
H22 H 0.637(6) 0.331(5) 0.5740(12) 0.058(12) Uiso 1 1 d . . . . .
C21 C 0.6384(3) 0.2447(3) 0.52644(7) 0.0271(5) Uani 1 1 d . . . . .
H21 H 0.732(4) 0.303(3) 0.5186(8) 0.018(7) Uiso 1 1 d . . . . .
N102 N 0.3620(3) 0.3077(3) 0.39591(7) 0.0305(5) Uani 1 1 d . . . . .
H10A H 0.338(4) 0.223(4) 0.3851(9) 0.027(8) Uiso 1 1 d . . . . .
H10B H 0.477(7) 0.330(5) 0.3930(14) 0.065(14) Uiso 1 1 d . . . . .
N101 N -0.6969(3) 0.5773(3) 0.86557(7) 0.0296(5) Uani 1 1 d . . . . .
H10C H -0.747(6) 0.504(4) 0.8755(12) 0.039(11) Uiso 1 1 d . . . . .
H10D H -0.770(4) 0.652(4) 0.8674(9) 0.030(8) Uiso 1 1 d . . . . .
C104 C -0.1706(3) 0.4320(3) 0.64994(7) 0.0261(5) Uani 1 1 d . . . . .
C103 C -0.2443(4) 0.4477(3) 0.67762(7) 0.0273(5) Uani 1 1 d . . . . .
C102 C -0.3230(4) 0.4673(3) 0.70839(7) 0.0264(5) Uani 1 1 d . . . . .
C101 C -0.3917(4) 0.4876(3) 0.73598(8) 0.0271(6) Uani 1 1 d . . . . .
C110 C -0.4710(4) 0.5115(3) 0.76856(7) 0.0253(6) Uani 1 1 d . . . . .
C115 C -0.5086(3) 0.4008(3) 0.79041(7) 0.0283(5) Uani 1 1 d . . . . .
H115 H -0.485(4) 0.309(3) 0.7826(8) 0.016(7) Uiso 1 1 d . . . . .
C114 C -0.5863(4) 0.4221(3) 0.82206(7) 0.0268(6) Uani 1 1 d . . . . .
H114 H -0.614(4) 0.344(4) 0.8372(9) 0.033(9) Uiso 1 1 d . . . . .
C113 C -0.6263(4) 0.5555(3) 0.83282(7) 0.0266(6) Uani 1 1 d . . . . .
C112 C -0.5888(3) 0.6659(3) 0.81115(7) 0.0281(5) Uani 1 1 d . . . . .
H112 H -0.626(5) 0.760(5) 0.8182(11) 0.047(11) Uiso 1 1 d . . . . .
C111 C -0.5120(3) 0.6452(3) 0.77956(7) 0.0278(6) Uani 1 1 d . . . . .
H111 H -0.494(4) 0.725(4) 0.7657(9) 0.030(8) Uiso 1 1 d . . . . .
C105 C -0.0896(4) 0.4132(3) 0.61943(7) 0.0278(5) Uani 1 1 d . . . . .
C106 C -0.0184(3) 0.3957(3) 0.59175(7) 0.0274(5) Uani 1 1 d . . . . .
C107 C 0.0547(3) 0.3765(3) 0.56038(7) 0.0277(5) Uani 1 1 d . . . . .
C108 C 0.1157(3) 0.3625(3) 0.53164(7) 0.0267(6) Uani 1 1 d . . . . .
C120 C 0.1795(3) 0.3485(3) 0.49741(7) 0.0253(5) Uani 1 1 d . . . . .
C125 C 0.1008(4) 0.2576(3) 0.47414(8) 0.0285(6) Uani 1 1 d . . . . .
H125 H 0.008(4) 0.204(4) 0.4804(9) 0.027(8) Uiso 1 1 d . . . . .
C124 C 0.1621(4) 0.2441(3) 0.44074(7) 0.0281(6) Uani 1 1 d . . . . .
H124 H 0.107(5) 0.183(4) 0.4255(10) 0.036(9) Uiso 1 1 d . . . . .
C123 C 0.3029(3) 0.3197(3) 0.42971(7) 0.0250(5) Uani 1 1 d . . . . .
C122 C 0.3796(3) 0.4124(3) 0.45264(7) 0.0270(5) Uani 1 1 d . . . . .
H122 H 0.480(4) 0.466(3) 0.4443(9) 0.022(7) Uiso 1 1 d . . . . .
C121 C 0.3188(3) 0.4260(3) 0.48592(7) 0.0266(5) Uani 1 1 d . . . . .
H121 H 0.373(5) 0.485(4) 0.5013(12) 0.034(10) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 H1A 0.90(4) . ?
N1 H1B 0.86(4) . ?
N1 C13 1.398(4) . ?
N2 H2A 0.88(6) . ?
N2 H2B 0.88(5) . ?
N2 C23 1.394(4) . ?
C4 C3 1.215(4) . ?
C4 C5 1.356(4) . ?
C3 C2 1.357(4) . ?
C2 C1 1.219(4) . ?
C1 C10 1.424(4) . ?
C10 C15 1.399(4) . ?
C10 C11 1.407(4) . ?
C15 H15 0.91(4) . ?
C15 C14 1.387(4) . ?
C14 H14 0.97(4) . ?
C14 C13 1.393(4) . ?
C13 C12 1.395(4) . ?
C12 H12 0.95(3) . ?
C12 C11 1.378(4) . ?
C11 H11 1.03(3) . ?
C5 C6 1.223(4) . ?
C6 C7 1.352(4) . ?
C7 C8 1.218(4) . ?
C8 C20 1.424(4) . ?
C20 C25 1.393(4) . ?
C20 C21 1.403(4) . ?
C25 H25 0.98(5) . ?
C25 C24 1.387(4) . ?
C24 H24 0.95(4) . ?
C24 C23 1.402(4) . ?
C23 C22 1.388(4) . ?
C22 H22 0.98(5) . ?
C22 C21 1.383(4) . ?
C21 H21 0.98(3) . ?
N102 H10A 0.94(4) . ?
N102 H10B 0.93(5) . ?
N102 C123 1.393(4) . ?
N101 H10C 0.90(5) . ?
N101 H10D 0.93(4) . ?
N101 C113 1.400(4) . ?
C104 C103 1.227(4) . ?
C104 C105 1.353(4) . ?
C103 C102 1.355(4) . ?
C102 C101 1.213(4) . ?
C101 C110 1.425(4) . ?
C110 C115 1.399(4) . ?
C110 C111 1.404(4) . ?
C115 H115 0.96(3) . ?
C115 C114 1.384(4) . ?
C114 H114 0.98(4) . ?
C114 C113 1.395(4) . ?
C113 C112 1.393(4) . ?
C112 H112 0.99(4) . ?
C112 C111 1.378(4) . ?
C111 H111 0.95(4) . ?
C105 C106 1.221(4) . ?
C106 C107 1.356(4) . ?
C107 C108 1.219(4) . ?
C108 C120 1.423(4) . ?
C120 C125 1.404(4) . ?
C120 C121 1.400(4) . ?
C125 H125 0.92(4) . ?
C125 C124 1.385(4) . ?
C124 H124 0.94(4) . ?
C124 C123 1.394(4) . ?
C123 C122 1.400(4) . ?
C122 H122 1.00(4) . ?
C122 C121 1.380(4) . ?
C121 H121 0.93(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
H1A N1 H1B 106(4) . . ?
C13 N1 H1A 118(3) . . ?
C13 N1 H1B 115(3) . . ?
H2A N2 H2B 125(5) . . ?
C23 N2 H2A 106(4) . . ?
C23 N2 H2B 114(3) . . ?
C3 C4 C5 178.0(3) . . ?
C4 C3 C2 177.8(3) . . ?
C1 C2 C3 177.8(3) . . ?
C2 C1 C10 176.0(3) . . ?
C15 C10 C1 122.0(3) . . ?
C15 C10 C11 118.7(3) . . ?
C11 C10 C1 119.3(3) . . ?
C10 C15 H15 117(2) . . ?
C14 C15 C10 120.3(3) . . ?
C14 C15 H15 123(2) . . ?
C15 C14 H14 117(2) . . ?
C15 C14 C13 120.7(3) . . ?
C13 C14 H14 122(2) . . ?
C14 C13 N1 120.6(3) . . ?
C14 C13 C12 119.1(3) . . ?
C12 C13 N1 120.3(3) . . ?
C13 C12 H12 122.4(18) . . ?
C11 C12 C13 120.6(3) . . ?
C11 C12 H12 117.0(18) . . ?
C10 C11 H11 119.4(19) . . ?
C12 C11 C10 120.5(3) . . ?
C12 C11 H11 120.1(19) . . ?
C6 C5 C4 178.6(3) . . ?
C5 C6 C7 178.3(3) . . ?
C8 C7 C6 178.1(3) . . ?
C7 C8 C20 176.5(3) . . ?
C25 C20 C8 121.3(2) . . ?
C25 C20 C21 118.7(2) . . ?
C21 C20 C8 120.0(2) . . ?
C20 C25 H25 119(3) . . ?
C24 C25 C20 121.2(2) . . ?
C24 C25 H25 120(3) . . ?
C25 C24 H24 116(2) . . ?
C25 C24 C23 119.8(2) . . ?
C23 C24 H24 124(2) . . ?
N2 C23 C24 120.0(2) . . ?
C22 C23 N2 120.9(3) . . ?
C22 C23 C24 119.1(2) . . ?
C23 C22 H22 123(3) . . ?
C21 C22 C23 121.2(3) . . ?
C21 C22 H22 116(3) . . ?
C20 C21 H21 121.4(18) . . ?
C22 C21 C20 120.1(3) . . ?
C22 C21 H21 118.5(19) . . ?
H10A N102 H10B 110(4) . . ?
C123 N102 H10A 115(2) . . ?
C123 N102 H10B 115(3) . . ?
H10C N101 H10D 109(4) . . ?
C113 N101 H10C 116(3) . . ?
C113 N101 H10D 116(2) . . ?
C103 C104 C105 179.4(3) . . ?
C104 C103 C102 178.7(3) . . ?
C101 C102 C103 178.5(3) . . ?
C102 C101 C110 179.5(3) . . ?
C115 C110 C101 120.2(2) . . ?
C115 C110 C111 118.6(3) . . ?
C111 C110 C101 121.3(2) . . ?
C110 C115 H115 118.8(19) . . ?
C114 C115 C110 120.9(3) . . ?
C114 C115 H115 120.2(19) . . ?
C115 C114 H114 121(2) . . ?
C115 C114 C113 120.1(2) . . ?
C113 C114 H114 119(2) . . ?
C114 C113 N101 120.0(3) . . ?
C112 C113 N101 120.8(3) . . ?
C112 C113 C114 119.1(3) . . ?
C113 C112 H112 119(2) . . ?
C111 C112 C113 121.0(3) . . ?
C111 C112 H112 120(2) . . ?
C110 C111 H111 123(2) . . ?
C112 C111 C110 120.3(3) . . ?
C112 C111 H111 116(2) . . ?
C106 C105 C104 179.2(3) . . ?
C105 C106 C107 177.7(3) . . ?
C108 C107 C106 177.5(3) . . ?
C107 C108 C120 177.3(3) . . ?
C125 C120 C108 120.2(2) . . ?
C121 C120 C108 121.3(2) . . ?
C121 C120 C125 118.5(2) . . ?
C120 C125 H125 122(2) . . ?
C124 C125 C120 120.3(3) . . ?
C124 C125 H125 118(2) . . ?
C125 C124 H124 119(2) . . ?
C125 C124 C123 120.8(3) . . ?
C123 C124 H124 120(2) . . ?
N102 C123 C124 120.5(2) . . ?
N102 C123 C122 120.4(2) . . ?
C124 C123 C122 119.0(2) . . ?
C123 C122 H122 118(2) . . ?
C121 C122 C123 120.3(3) . . ?
C121 C122 H122 122(2) . . ?
C120 C121 H121 119(3) . . ?
C122 C121 C120 121.0(3) . . ?
C122 C121 H121 120(3) . . ?

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
N1 C13 C12 C11 176.2(3) . . . . ?
N2 C23 C22 C21 178.0(2) . . . . ?
C1 C10 C15 C14 -179.7(3) . . . . ?
C1 C10 C11 C12 178.6(3) . . . . ?
C10 C15 C14 C13 0.6(4) . . . . ?
C15 C10 C11 C12 -1.4(4) . . . . ?
C15 C14 C13 N1 -177.4(3) . . . . ?
C15 C14 C13 C12 -0.5(4) . . . . ?
C14 C13 C12 C11 -0.7(4) . . . . ?
C13 C12 C11 C10 1.6(4) . . . . ?
C11 C10 C15 C14 0.3(4) . . . . ?
C8 C20 C25 C24 -179.8(2) . . . . ?
C8 C20 C21 C22 179.7(2) . . . . ?
C20 C25 C24 C23 0.2(4) . . . . ?
C25 C20 C21 C22 -0.7(4) . . . . ?
C25 C24 C23 N2 -178.1(2) . . . . ?
C25 C24 C23 C22 -0.9(4) . . . . ?
C24 C23 C22 C21 0.9(4) . . . . ?
C23 C22 C21 C20 -0.1(4) . . . . ?
C21 C20 C25 C24 0.7(4) . . . . ?
N102 C123 C122 C121 178.8(2) . . . . ?
N101 C113 C112 C111 177.0(3) . . . . ?
C101 C110 C115 C114 -179.7(3) . . . . ?
C101 C110 C111 C112 179.9(3) . . . . ?
C110 C115 C114 C113 -0.8(4) . . . . ?
C115 C110 C111 C112 -0.4(4) . . . . ?
C115 C114 C113 N101 -176.8(3) . . . . ?
C115 C114 C113 C112 0.7(4) . . . . ?
C114 C113 C112 C111 -0.5(4) . . . . ?
C113 C112 C111 C110 0.3(4) . . . . ?
C111 C110 C115 C114 0.7(4) . . . . ?
C108 C120 C125 C124 179.7(2) . . . . ?
C108 C120 C121 C122 -179.7(2) . . . . ?
C120 C125 C124 C123 0.3(4) . . . . ?
C125 C120 C121 C122 -0.9(4) . . . . ?
C125 C124 C123 N102 -178.8(2) . . . . ?
C125 C124 C123 C122 -1.5(4) . . . . ?
C124 C123 C122 C121 1.5(4) . . . . ?
C123 C122 C121 C120 -0.3(4) . . . . ?
C121 C120 C125 C124 0.9(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 1.729
_oxdiff_exptl_absorpt_empirical_full_min 0.557
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.4(10)
2 -0.4(10)

####################################################################### 
# 
# 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_jp-01-52
_database_code_depnum_ccdc_archive 'CCDC 2244316'
loop_
_audit_author_name
_audit_author_address
'Jarred Potter'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2023-02-24 deposited with the CCDC.	2023-04-06 downloaded from the CCDC.
;
_audit_creation_date             2023-01-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H11 N O, H2 O'
_chemical_formula_sum            'C12 H13 N O2'
_chemical_formula_weight         203.23
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   7.81540(10)
_cell_length_b                   6.00420(10)
_cell_length_c                   24.4944(4)
_cell_angle_alpha                90
_cell_angle_beta                 98.117(2)
_cell_angle_gamma                90
_cell_volume                     1137.89(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6172
_cell_measurement_temperature    100.15
_cell_measurement_theta_min      3.6160
_cell_measurement_theta_max      75.4910
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.657
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.949
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            8892
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.548
_diffrn_reflns_theta_min         3.646
_diffrn_ambient_temperature      100.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.949
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2009
_reflns_number_total             2249
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.139
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     142
_refine_ls_number_reflns         2249
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0332
_refine_ls_restrained_S_all      1.054
_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)+(0.0426P)²+0.2969P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0885
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Free rotating group:
 O2(H2A,H2B)
1.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C12(H12), C13(H13), C14(H14)
1.c Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C31(H31A,H31B,H31C)
1.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   mixed
_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
O1 O 0.36660(9) 0.82082(12) 0.69555(3) 0.02405(19) Uani 1 1 d . . . . .
H1 H 0.446998 0.726800 0.698976 0.036 Uiso 1 1 calc R U . . .
N1 N 0.29963(11) -0.27794(16) 0.37857(4) 0.0256(2) Uani 1 1 d . . . . .
C4 C 0.23292(13) 0.57828(18) 0.62510(4) 0.0240(2) Uani 1 1 d . . . . .
C3 C 0.24899(13) 0.46116(19) 0.58633(4) 0.0249(2) Uani 1 1 d . . . . .
C2 C 0.26419(13) 0.32077(19) 0.54271(4) 0.0252(2) Uani 1 1 d . . . . .
C1 C 0.27555(13) 0.19429(19) 0.50569(4) 0.0257(2) Uani 1 1 d . . . . .
C10 C 0.28523(13) 0.03540(18) 0.46247(4) 0.0228(2) Uani 1 1 d . . . . .
C11 C 0.37896(13) 0.07814(19) 0.41905(4) 0.0256(2) Uani 1 1 d . . . . .
H11 H 0.439085 0.214878 0.417273 0.031 Uiso 1 1 calc R U . . .
C12 C 0.38255(14) -0.0822(2) 0.37875(4) 0.0266(2) Uani 1 1 d . . . . .
H12 H 0.447333 -0.052208 0.349553 0.032 Uiso 1 1 calc R U . . .
C13 C 0.21017(14) -0.31759(19) 0.42031(4) 0.0259(2) Uani 1 1 d . . . . .
H13 H 0.150514 -0.455290 0.420758 0.031 Uiso 1 1 calc R U . . .
C14 C 0.20000(14) -0.16869(19) 0.46282(4) 0.0255(2) Uani 1 1 d . . . . .
H14 H 0.135947 -0.204827 0.491819 0.031 Uiso 1 1 calc R U . . .
C30 C 0.20802(13) 0.71422(18) 0.67383(4) 0.0229(2) Uani 1 1 d . . . . .
C32 C 0.08020(15) 0.9016(2) 0.65675(5) 0.0332(3) Uani 1 1 d . . . . .
H32A H 0.068984 0.995279 0.688815 0.050 Uiso 1 1 calc R U . . .
H32B H -0.032712 0.838012 0.642393 0.050 Uiso 1 1 calc R U . . .
H32C H 0.122083 0.991967 0.628068 0.050 Uiso 1 1 calc R U . . .
C31 C 0.14608(15) 0.5640(2) 0.71738(5) 0.0321(3) Uani 1 1 d . . . . .
H31A H 0.231269 0.445996 0.727534 0.048 Uiso 1 1 calc R U . . .
H31B H 0.034881 0.497140 0.702461 0.048 Uiso 1 1 calc R U . . .
H31C H 0.132353 0.652487 0.750103 0.048 Uiso 1 1 calc R U . . .
O2 O 0.64227(10) 0.56559(13) 0.70873(3) 0.02678(19) Uani 1 1 d G . . . .
H2A H 0.642161 0.480678 0.737512 0.040 Uiso 1 1 d G U . . .
H2B H 0.662431 0.475143 0.682632 0.040 Uiso 1 1 d G U . . .


_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
O1 H1 0.8400 . ?
O1 C30 1.4292(12) . ?
N1 C12 1.3416(15) . ?
N1 C13 1.3390(14) . ?
C4 C3 1.2024(15) . ?
C4 C30 1.4812(14) . ?
C3 C2 1.3792(15) . ?
C2 C1 1.1957(16) . ?
C1 C10 1.4349(15) . ?
C10 C11 1.3978(15) . ?
C10 C14 1.3954(16) . ?
C11 H11 0.9500 . ?
C11 C12 1.3821(16) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C13 C14 1.3831(15) . ?
C14 H14 0.9500 . ?
C30 C32 1.5233(15) . ?
C30 C31 1.5270(15) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C31 H31A 0.9800 . ?
C31 H31B 0.9800 . ?
C31 H31C 0.9800 . ?
O2 H2A 0.8701 . ?
O2 H2B 0.8700 . ?

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
C30 O1 H1 109.5 . . ?
C13 N1 C12 117.21(9) . . ?
C3 C4 C30 177.29(11) . . ?
C4 C3 C2 177.91(12) . . ?
C1 C2 C3 178.16(12) . . ?
C2 C1 C10 177.50(12) . . ?
C11 C10 C1 121.81(10) . . ?
C14 C10 C1 120.29(10) . . ?
C14 C10 C11 117.89(10) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 C10 118.77(10) . . ?
C12 C11 H11 120.6 . . ?
N1 C12 C11 123.64(10) . . ?
N1 C12 H12 118.2 . . ?
C11 C12 H12 118.2 . . ?
N1 C13 H13 118.3 . . ?
N1 C13 C14 123.48(11) . . ?
C14 C13 H13 118.3 . . ?
C10 C14 H14 120.5 . . ?
C13 C14 C10 119.00(10) . . ?
C13 C14 H14 120.5 . . ?
O1 C30 C4 109.94(8) . . ?
O1 C30 C32 105.79(9) . . ?
O1 C30 C31 110.37(8) . . ?
C4 C30 C32 109.96(9) . . ?
C4 C30 C31 109.16(9) . . ?
C32 C30 C31 111.57(9) . . ?
C30 C32 H32A 109.5 . . ?
C30 C32 H32B 109.5 . . ?
C30 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C30 C31 H31A 109.5 . . ?
C30 C31 H31B 109.5 . . ?
C30 C31 H31C 109.5 . . ?
H31A C31 H31B 109.5 . . ?
H31A C31 H31C 109.5 . . ?
H31B C31 H31C 109.5 . . ?
H2A O2 H2B 104.5 . . ?

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
N1 C13 C14 C10 0.72(16) . . . . ?
C1 C10 C11 C12 -179.89(9) . . . . ?
C1 C10 C14 C13 179.33(10) . . . . ?
C10 C11 C12 N1 0.49(16) . . . . ?
C11 C10 C14 C13 -0.69(15) . . . . ?
C12 N1 C13 C14 -0.13(16) . . . . ?
C13 N1 C12 C11 -0.49(15) . . . . ?
C14 C10 C11 C12 0.13(15) . . . . ?

_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_pjl596_auto
_database_code_depnum_ccdc_archive 'CCDC 2244317'
loop_
_audit_author_name
_audit_author_address
'Jarred Potter'
;The University of Western Australia
Australia
;
_audit_update_record             
;
2023-02-24 deposited with the CCDC.	2023-04-06 downloaded from the CCDC.
;
_audit_creation_date             2023-01-09
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H13 N S'
_chemical_formula_sum            'C17 H13 N S'
_chemical_formula_weight         263.34
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'S1 N1 C20 H10'
_chemical_oxdiff_usercomment     'Jarred for Low'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 '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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
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'

_cell_length_a                   9.17990(10)
_cell_length_b                   6.90650(10)
_cell_length_c                   20.6965(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1312.18(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11131
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      74.9080
_cell_measurement_theta_min      6.7270
_shelx_estimated_absorpt_T_max   0.750
_shelx_estimated_absorpt_T_min   0.609
_exptl_absorpt_coefficient_mu    2.036
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.484
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.58a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear dark orange'
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             552
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-5 6 2 0.0941
3 -10 -2 0.1052
-4 6 3 0.0891
2 -8 -3 0.0939
-1 6 4 0.0845
2 -5 -4 0.0794
0 2 4 0.0751
-2 -5 -4 0.0918
-5 -7 0 0.0751
2 4 -4 0.0764
3 3 4 0.0672
-2 -8 3 0.1073
-4 1 -4 0.0790
5 8 0 0.0776
3 -11 1 0.1092
2 5 4 0.0756
2 0 -4 0.0750
3 2 4 0.0647
-3 7 -3 0.1037
3 -7 3 0.0871
-5 5 -2 0.0880
3 -10 2 0.1014
5 7 0 0.0790

_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-4.8346 5.9196 1.7245 -0.1140 0.8660 -0.4868
2.7124 -10.4865 -1.9214 0.1300 -0.9915 0.0091
-3.6653 5.8728 2.9416 -0.4070 0.8538 -0.3248
2.1543 -8.4728 -3.0781 0.4300 -0.9028 0.0090
-1.3898 5.6237 3.9336 -0.6880 0.7257 -0.0090
1.9870 -4.7777 -3.9131 0.6825 -0.7198 0.1271
-0.4939 2.2181 4.4042 -0.8785 0.4776 -0.0089
-2.2059 -5.3802 -3.7569 0.7587 -0.4129 -0.5038
-5.1510 -6.7596 0.0527 0.0086 -0.0023 -1.0000
2.0100 4.4027 -3.9545 0.8654 -0.1605 0.4746
3.3822 2.8220 3.5682 -0.8013 0.1494 0.5793
-1.6757 -7.7721 3.4308 -0.8280 -0.1089 -0.5500
-3.6298 1.1182 -3.5350 0.8764 0.1146 -0.4677
4.7833 7.9984 -0.1824 0.0531 0.0987 0.9937
3.2724 -10.9579 0.8185 -0.4768 -0.8770 0.0598
1.9473 5.1062 3.8782 -0.7823 0.4250 0.4555
2.3075 0.3610 -4.1299 0.8171 -0.4445 0.3671
2.7270 1.7890 3.9400 -0.8810 0.1635 0.4439
-2.6424 7.1563 -3.2304 0.8983 0.4280 -0.0998
2.8321 -6.8578 3.2115 -0.8941 -0.4260 0.1385
-5.1172 4.5686 -1.7204 0.5998 0.5692 -0.5624
2.7334 -10.0589 2.1448 -0.7257 -0.6880 0.0092
4.9892 7.3229 -0.2176 0.0418 0.0385 0.9984

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            22761
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.030
_diffrn_reflns_theta_min         4.272
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     99.00 173.00   0.50    0.05    --  102.37  45.00-150.00  148
  2  ω     86.00 175.00   0.50    0.05    --  102.37  61.00 -90.00  178
  3  ω    140.00 173.00   0.50    0.05    --  102.37  45.00 120.00   66
  4  ω     91.00 130.00   0.50    0.05    --  102.37  45.00 120.00   78
  5  ω    -28.00  24.00   0.50    0.05    --   45.98 -19.00 120.00  104
  6  ω     17.00  97.00   0.50    0.05    --   45.98-132.00 127.00  160
  7  ω     20.00 101.00   0.50    0.05    --   45.98-138.00 -49.00  162
  8  ω     30.00 121.00   0.50    0.05    --  102.37-138.00 -49.00  182
  9  ω     30.00 111.00   0.50    0.05    --  102.37-125.00   0.00  162
 10  ω     30.00 105.00   0.50    0.05    --  102.37 -94.00 -30.00  150
 11  ω     30.00 117.00   0.50    0.05    --  102.37-132.00 127.00  174
 12  ω     51.00 105.00   0.50    0.05    --  102.37 -94.00 150.00  108
 13  ω     68.00 102.00   0.50    0.05    --  102.37 -94.00 120.00   68
 14  ω    -28.00  24.00   0.50    0.05    --   45.98 -19.00 -90.00  104
 15  ω    -28.00  24.00   0.50    0.05    --   45.98 -19.00-180.00  104
 16  ω     31.00  68.00   0.50    0.05    --  102.37 -61.00 -90.00   74
 17  ω     31.00  69.00   0.50    0.05    --  102.37 -61.00 -60.00   76
 18  ω     31.00  64.00   0.50    0.05    --  102.37 -61.00  90.00   66
 19  ω     30.00  69.00   0.50    0.05    --  102.37 -61.00 120.00   78
 20  ω     69.00 175.00   0.50    0.05    --  102.37 132.00-162.00  212
 21  ω     95.00 120.00   0.50    0.05    --  102.37 138.00  13.00   50
 22  ω     65.00 119.00   0.50    0.05    --   45.98 138.00  13.00  108
 23  ω    -28.00  30.00   0.50    0.05    --  -45.98  19.00   0.00  116
 24  ω    -73.00 -30.00   0.50    0.05    -- -102.37  61.00-120.00   86
 25  ω    -73.00 -30.00   0.50    0.05    -- -102.37  61.00-150.00   86
 26  ω   -107.00 -30.00   0.50    0.05    -- -102.37  77.00  30.00  154
 27  ω   -107.00 -30.00   0.50    0.05    -- -102.37 105.00  86.76  154
 28  ω   -121.00 -30.00   0.50    0.05    -- -102.37 138.00  13.00  182
 29  ω   -101.00 -20.00   0.50    0.05    --  -45.98 138.00  13.00  162
 30  ω    -97.00 -17.00   0.50    0.05    --  -45.98 132.00-162.00  160
 31  ω   -117.00 -30.00   0.50    0.05    -- -102.37 132.00-162.00  174
 32  ω   -177.00 -89.00   0.50    0.05    -- -102.37 -15.00 -60.00  176
 33  ω   -175.00 -87.00   0.50    0.05    -- -102.37 -59.00  32.47  176
 34  ω   -118.00 -65.00   0.50    0.05    --  -45.98-138.00 -49.00  106
 35  ω   -118.00 -73.00   0.50    0.05    --  -45.98-125.00-180.00   90
 36  ω   -175.00 -83.00   0.50    0.05    -- -102.37 -94.00-120.00  184
 37  ω   -118.00 -23.00   0.50    0.05    --  -45.98 -77.00  60.00  190
 38  ω   -118.00 -69.00   0.50    0.05    --  -45.98-132.00 127.00   98
 39  ω   -175.00 -69.00   0.50    0.05    -- -102.37-132.00 127.00  212
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0288330000
_diffrn_orient_matrix_UB_12      0.0190419000
_diffrn_orient_matrix_UB_13      -0.2123017000
_diffrn_orient_matrix_UB_21      -0.0794560000
_diffrn_orient_matrix_UB_22      0.0614273000
_diffrn_orient_matrix_UB_23      0.0685926000
_diffrn_orient_matrix_UB_31      0.1449101000
_diffrn_orient_matrix_UB_32      0.0374691000
_diffrn_orient_matrix_UB_33      -0.0046460000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.886
_reflns_Friedel_fraction_full    0.970
_reflns_Friedel_fraction_max     0.932
_reflns_number_gt                2528
_reflns_number_total             2619
_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 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.58a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.192
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 1151 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.002(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     224
_refine_ls_number_reflns         2619
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0331
_refine_ls_R_factor_gt           0.0317
_refine_ls_restrained_S_all      1.054
_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)+(0.0558P)²+0.1885P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0836
_refine_ls_wR_factor_ref         0.0855
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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 0.02344(6) 0.47950(7) 0.28815(3) 0.02211(18) Uani 1 1 d . . . . .
N1 N 1.3996(3) 0.4796(4) 0.71130(12) 0.0270(5) Uani 1 1 d . . . . .
C14 C 0.3064(3) 0.5368(4) 0.31506(14) 0.0223(5) Uani 1 1 d . . . . .
C3 C 0.7955(3) 0.5239(4) 0.51950(14) 0.0226(5) Uani 1 1 d . . . . .
C10 C 0.4203(3) 0.5206(3) 0.42029(13) 0.0203(5) Uani 1 1 d . . . . .
C23 C 1.2799(3) 0.4902(4) 0.67134(13) 0.0216(5) Uani 1 1 d . . . . .
C21 C 1.0939(2) 0.6784(4) 0.61731(11) 0.0224(5) Uani 1 1 d . . . . .
C1 C 0.5510(3) 0.5258(3) 0.45804(13) 0.0211(5) Uani 1 1 d . . . . .
C12 C 0.1600(3) 0.4765(4) 0.40962(12) 0.0225(5) Uani 1 1 d . . . . .
C25 C 1.0965(3) 0.3319(4) 0.60613(12) 0.0230(5) Uani 1 1 d . . . . .
C24 C 1.2189(2) 0.3212(4) 0.64523(12) 0.0230(5) Uani 1 1 d . . . . .
C2 C 0.6671(3) 0.5269(3) 0.48615(13) 0.0226(5) Uani 1 1 d . . . . .
C4 C 0.9056(3) 0.5197(4) 0.55139(12) 0.0223(6) Uani 1 1 d . . . . .
C22 C 1.2158(2) 0.6685(4) 0.65676(12) 0.0235(6) Uani 1 1 d . . . . .
C13 C 0.1706(3) 0.4989(3) 0.34249(13) 0.0191(5) Uani 1 1 d . . . . .
C16 C -0.1325(3) 0.4617(4) 0.34042(14) 0.0237(5) Uani 1 1 d . . . . .
C20 C 1.0321(3) 0.5108(4) 0.59154(14) 0.0218(6) Uani 1 1 d . . . . .
C11 C 0.2841(3) 0.4871(4) 0.44779(13) 0.0236(6) Uani 1 1 d . . . . .
C15 C 0.4304(3) 0.5468(4) 0.35322(14) 0.0220(5) Uani 1 1 d . . . . .
H24 H 1.262(3) 0.198(4) 0.6533(14) 0.023(7) Uiso 1 1 d . . . . .
H25 H 1.059(3) 0.216(5) 0.5871(15) 0.032(8) Uiso 1 1 d . . . . .
H16A H -0.131(2) 0.347(4) 0.3668(13) 0.015(6) Uiso 1 1 d . . . . .
H21 H 1.052(3) 0.811(5) 0.6075(15) 0.029(8) Uiso 1 1 d . . . . .
H16B H -0.143(3) 0.575(4) 0.3674(15) 0.019(7) Uiso 1 1 d . . . . .
H1A H 1.438(3) 0.579(5) 0.7231(16) 0.025(8) Uiso 1 1 d . . . . .
H12 H 0.070(4) 0.446(5) 0.4285(17) 0.032(8) Uiso 1 1 d . . . . .
H1B H 1.437(3) 0.368(6) 0.7166(18) 0.041(9) Uiso 1 1 d . . . . .
H11 H 0.272(4) 0.467(4) 0.494(2) 0.033(9) Uiso 1 1 d . . . . .
H16C H -0.217(3) 0.450(4) 0.3113(16) 0.027(8) Uiso 1 1 d . . . . .
H22 H 1.255(3) 0.784(5) 0.6742(14) 0.029(7) Uiso 1 1 d . . . . .
H14 H 0.312(3) 0.560(4) 0.2698(15) 0.018(7) Uiso 1 1 d . . . . .
H15 H 0.517(3) 0.580(5) 0.3335(16) 0.033(8) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C13 1.763(3) . ?
S1 C16 1.798(3) . ?
N1 C23 1.377(4) . ?
N1 H1A 0.81(3) . ?
N1 H1B 0.85(4) . ?
C14 C13 1.395(4) . ?
C14 C15 1.387(4) . ?
C14 H14 0.95(3) . ?
C3 C2 1.366(4) . ?
C3 C4 1.208(4) . ?
C10 C1 1.432(4) . ?
C10 C11 1.393(4) . ?
C10 C15 1.403(4) . ?
C23 C24 1.403(4) . ?
C23 C22 1.398(3) . ?
C21 C22 1.387(3) . ?
C21 C20 1.395(4) . ?
C21 H21 1.01(3) . ?
C1 C2 1.214(4) . ?
C12 C13 1.401(4) . ?
C12 C11 1.388(4) . ?
C12 H12 0.94(3) . ?
C25 C24 1.387(3) . ?
C25 C20 1.403(4) . ?
C25 H25 0.95(3) . ?
C24 H24 0.95(3) . ?
C4 C20 1.429(4) . ?
C22 H22 0.95(3) . ?
C16 H16A 0.96(3) . ?
C16 H16B 0.97(3) . ?
C16 H16C 0.99(3) . ?
C11 H11 0.98(4) . ?
C15 H15 0.92(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
C13 S1 C16 103.38(13) . . ?
C23 N1 H1A 119(2) . . ?
C23 N1 H1B 116(2) . . ?
H1A N1 H1B 124(4) . . ?
C13 C14 H14 118.7(16) . . ?
C15 C14 C13 120.7(3) . . ?
C15 C14 H14 120.5(16) . . ?
C4 C3 C2 177.2(3) . . ?
C11 C10 C1 122.2(2) . . ?
C11 C10 C15 119.0(2) . . ?
C15 C10 C1 118.8(2) . . ?
N1 C23 C24 120.4(2) . . ?
N1 C23 C22 120.8(2) . . ?
C22 C23 C24 118.8(2) . . ?
C22 C21 C20 120.8(2) . . ?
C22 C21 H21 118.1(17) . . ?
C20 C21 H21 121.1(17) . . ?
C2 C1 C10 175.4(3) . . ?
C13 C12 H12 120(2) . . ?
C11 C12 C13 120.1(2) . . ?
C11 C12 H12 120(2) . . ?
C24 C25 C20 120.9(2) . . ?
C24 C25 H25 119.4(18) . . ?
C20 C25 H25 119.6(18) . . ?
C23 C24 H24 120.4(17) . . ?
C25 C24 C23 120.3(2) . . ?
C25 C24 H24 119.2(17) . . ?
C1 C2 C3 177.9(3) . . ?
C3 C4 C20 177.3(3) . . ?
C23 C22 H22 120.2(17) . . ?
C21 C22 C23 120.7(2) . . ?
C21 C22 H22 119.1(17) . . ?
C14 C13 S1 116.1(2) . . ?
C14 C13 C12 119.1(3) . . ?
C12 C13 S1 124.8(2) . . ?
S1 C16 H16A 112.8(14) . . ?
S1 C16 H16B 111.9(16) . . ?
S1 C16 H16C 105.4(19) . . ?
H16A C16 H16B 110(3) . . ?
H16A C16 H16C 107(2) . . ?
H16B C16 H16C 110(2) . . ?
C21 C20 C25 118.5(2) . . ?
C21 C20 C4 121.2(2) . . ?
C25 C20 C4 120.4(2) . . ?
C10 C11 H11 122(2) . . ?
C12 C11 C10 120.9(2) . . ?
C12 C11 H11 118(2) . . ?
C14 C15 C10 120.2(2) . . ?
C14 C15 H15 118(2) . . ?
C10 C15 H15 122(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
N1 C23 C24 C25 178.6(2) . . . . ?
N1 C23 C22 C21 -179.0(2) . . . . ?
C1 C10 C11 C12 -177.8(2) . . . . ?
C1 C10 C15 C14 178.1(2) . . . . ?
C24 C23 C22 C21 0.1(4) . . . . ?
C24 C25 C20 C21 0.0(4) . . . . ?
C24 C25 C20 C4 -179.8(2) . . . . ?
C22 C23 C24 C25 -0.5(4) . . . . ?
C22 C21 C20 C25 -0.4(4) . . . . ?
C22 C21 C20 C4 179.4(2) . . . . ?
C13 C14 C15 C10 -0.6(4) . . . . ?
C13 C12 C11 C10 0.2(4) . . . . ?
C16 S1 C13 C14 -173.11(19) . . . . ?
C16 S1 C13 C12 7.8(2) . . . . ?
C20 C21 C22 C23 0.3(4) . . . . ?
C20 C25 C24 C23 0.5(4) . . . . ?
C11 C10 C15 C14 -0.8(4) . . . . ?
C11 C12 C13 S1 177.42(17) . . . . ?
C11 C12 C13 C14 -1.6(4) . . . . ?
C15 C14 C13 S1 -177.3(2) . . . . ?
C15 C14 C13 C12 1.8(4) . . . . ?
C15 C10 C11 C12 1.0(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 1.218
_oxdiff_exptl_absorpt_empirical_full_min 0.825
