# Supplementary Information (SI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_B19955
_database_code_depnum_ccdc_archive 'CCDC 2371492'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2024-08-06 deposited with the CCDC.	2024-10-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_chemical_name_systematic        
rac-(3aR,9bR)-3a-hydroxy-3-phenyl-3a,4,5,9b-tetrahydronaphtho[2,1-d]thiazole-2(3H)-thione
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H15 N O S2'
_chemical_formula_sum            'C17 H15 N O S2'
_chemical_formula_weight         313.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_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.
;

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                   7.2278(8)
_cell_length_b                   22.429(6)
_cell_length_c                   9.660(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.99(3)
_cell_angle_gamma                90
_cell_volume                     1546.8(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1291
_cell_measurement_theta_min      2.7940
_cell_measurement_theta_max      28.6990

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.650
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    0.342
_shelx_estimated_absorpt_T_min   0.808
_shelx_estimated_absorpt_T_max   0.990
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 5 -5 0.1080
5 2 -5 0.1518
0 -4 5 0.1131
-1 1 -1 0.2079
0 1 0 0.0010
0 -1 0 0.0281
_exptl_absorpt_correction_T_min  0.900
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.98a (Rigaku Oxford Diffraction, 2023)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_reflns_number            19727
_diffrn_reflns_av_R_equivalents  0.0392
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.803
_diffrn_reflns_theta_max         27.103
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.927
_diffrn_reflns_point_group_measured_fraction_full 0.948
_reflns_number_total             6347
_reflns_number_gt                5327
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.850
_reflns_Friedel_fraction_max     0.856
_reflns_Friedel_fraction_full    0.896

_reflns_special_details          
;
 _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.
;

_computing_data_collection       'CrysAlisPro system (CCD 43.98a 64-bit)'
_computing_cell_refinement       'CrysAlisPro 1.171.43.98a (Rigaku OD, 2023)'
_computing_data_reduction        'CrysAlisPro 1.171.43.98a (Rigaku OD, 2023)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2015b)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          'Refined as a 2-component twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0561P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1109 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(5)
_chemical_absolute_configuration .
_refine_ls_number_reflns         6347
_refine_ls_number_parameters     194
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0326
_refine_ls_wR_factor_ref         0.0873
_refine_ls_wR_factor_gt          0.0829
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.985
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
C2 C 0.4213(5) 0.31897(14) 0.3925(3) 0.0412(7) Uani 1 1 d . . . . .
H2 H 0.393590 0.312751 0.290985 0.049 Uiso 1 1 calc R U . . .
C1 C 0.3323(4) 0.26808(14) 0.4632(3) 0.0386(7) Uani 1 1 d . . . . .
C4 C 0.6505(5) 0.23240(14) 0.4742(3) 0.0393(7) Uani 1 1 d . . . . .
S3 S 0.67459(10) 0.30906(4) 0.44679(8) 0.0483(2) Uani 1 1 d . . . . .
C8 C 0.1784(5) 0.33901(17) 0.6105(3) 0.0529(8) Uani 1 1 d . . . . .
H8A H 0.050663 0.328149 0.572311 0.063 Uiso 1 1 calc R U . . .
H8B H 0.179428 0.352393 0.706100 0.063 Uiso 1 1 calc R U . . .
N5 N 0.4699(4) 0.21760(12) 0.4700(3) 0.0396(6) Uani 1 1 d . . . . .
C14 C 0.3533(5) 0.38021(15) 0.4236(3) 0.0474(8) Uani 1 1 d . . . . .
C13 C 0.3995(6) 0.42847(18) 0.3450(4) 0.0629(10) Uani 1 1 d . . . . .
H13 H 0.473763 0.422339 0.275872 0.075 Uiso 1 1 calc R U . . .
C7 C 0.3027(5) 0.28414(15) 0.6118(3) 0.0438(7) Uani 1 1 d . . . . .
H7A H 0.244789 0.250834 0.652717 0.053 Uiso 1 1 calc R U . . .
H7B H 0.422845 0.291899 0.669107 0.053 Uiso 1 1 calc R U . . .
C12 C 0.3367(7) 0.48554(19) 0.3679(6) 0.0767(13) Uani 1 1 d . . . . .
H12 H 0.369202 0.517292 0.314636 0.092 Uiso 1 1 calc R U . . .
C10 C 0.1759(7) 0.44738(19) 0.5453(5) 0.0692(11) Uani 1 1 d . . . . .
H10 H 0.097188 0.453900 0.611326 0.083 Uiso 1 1 calc R U . . .
C9 C 0.2395(5) 0.38951(16) 0.5259(4) 0.0508(8) Uani 1 1 d . . . . .
C18 C 0.3665(7) 0.08004(19) 0.6556(5) 0.0677(11) Uani 1 1 d . . . . .
H18 H 0.381261 0.064933 0.746349 0.081 Uiso 1 1 calc R U . . .
C19 C 0.2774(7) 0.04627(19) 0.5465(6) 0.0777(13) Uani 1 1 d . . . . .
H19 H 0.231907 0.008648 0.563668 0.093 Uiso 1 1 calc R U . . .
C20 C 0.2555(7) 0.0682(2) 0.4113(6) 0.0753(13) Uani 1 1 d . . . . .
H20 H 0.196527 0.045094 0.337391 0.090 Uiso 1 1 calc R U . . .
C21 C 0.3210(5) 0.12467(17) 0.3852(4) 0.0560(9) Uani 1 1 d . . . . .
H21 H 0.305355 0.139759 0.294493 0.067 Uiso 1 1 calc R U . . .
S6 S 0.83398(10) 0.18635(4) 0.50250(8) 0.0475(2) Uani 1 1 d . . . . .
C11 C 0.2267(7) 0.4950(2) 0.4692(6) 0.0824(15) Uani 1 1 d . . . . .
H11 H 0.186650 0.533326 0.486430 0.099 Uiso 1 1 calc R U . . .
C16 C 0.4099(5) 0.15806(14) 0.4963(3) 0.0434(7) Uani 1 1 d . . . . .
C17 C 0.4346(5) 0.13611(15) 0.6325(4) 0.0518(8) Uani 1 1 d . . . . .
H17 H 0.495640 0.158721 0.706561 0.062 Uiso 1 1 calc R U . . .
O15 O 0.1665(3) 0.25350(11) 0.3751(2) 0.0466(5) Uani 1 1 d . . . . .
H15 H 0.097(8) 0.2349(17) 0.427(5) 0.070 Uiso 1 1 d . 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
C2 C14 1.505(5) . ?
C2 C1 1.523(4) . ?
C2 S3 1.837(3) . ?
C2 H2 0.9800 . ?
C1 O15 1.396(4) . ?
C1 N5 1.502(4) . ?
C1 C7 1.527(4) . ?
C4 N5 1.341(4) . ?
C4 S6 1.669(4) . ?
C4 S3 1.752(3) . ?
C8 C9 1.503(5) . ?
C8 C7 1.523(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
N5 C16 1.439(4) . ?
C14 C13 1.392(5) . ?
C14 C9 1.397(5) . ?
C13 C12 1.387(6) . ?
C13 H13 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C12 C11 1.370(8) . ?
C12 H12 0.9300 . ?
C10 C11 1.379(7) . ?
C10 C9 1.399(5) . ?
C10 H10 0.9300 . ?
C18 C19 1.374(7) . ?
C18 C17 1.381(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.382(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.388(6) . ?
C20 H20 0.9300 . ?
C21 C16 1.382(5) . ?
C21 H21 0.9300 . ?
C11 H11 0.9300 . ?
C16 C17 1.390(5) . ?
C17 H17 0.9300 . ?
O15 H15 0.87(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
C14 C2 C1 114.9(3) . . ?
C14 C2 S3 113.3(2) . . ?
C1 C2 S3 104.7(2) . . ?
C14 C2 H2 107.9 . . ?
C1 C2 H2 107.9 . . ?
S3 C2 H2 107.9 . . ?
O15 C1 N5 110.5(2) . . ?
O15 C1 C2 106.5(2) . . ?
N5 C1 C2 105.1(2) . . ?
O15 C1 C7 113.3(3) . . ?
N5 C1 C7 109.0(2) . . ?
C2 C1 C7 112.1(3) . . ?
N5 C4 S6 126.6(2) . . ?
N5 C4 S3 110.9(2) . . ?
S6 C4 S3 122.47(19) . . ?
C4 S3 C2 92.52(15) . . ?
C9 C8 C7 113.0(3) . . ?
C9 C8 H8A 109.0 . . ?
C7 C8 H8A 109.0 . . ?
C9 C8 H8B 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C4 N5 C16 122.9(3) . . ?
C4 N5 C1 116.7(3) . . ?
C16 N5 C1 119.4(2) . . ?
C13 C14 C9 119.2(3) . . ?
C13 C14 C2 119.2(3) . . ?
C9 C14 C2 121.6(3) . . ?
C12 C13 C14 121.2(4) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C8 C7 C1 110.6(3) . . ?
C8 C7 H7A 109.5 . . ?
C1 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C11 C12 C13 119.9(4) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C11 C10 C9 121.8(4) . . ?
C11 C10 H10 119.1 . . ?
C9 C10 H10 119.1 . . ?
C14 C9 C10 118.4(3) . . ?
C14 C9 C8 121.9(3) . . ?
C10 C9 C8 119.7(3) . . ?
C19 C18 C17 120.9(4) . . ?
C19 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C18 C19 C20 120.0(4) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C21 120.3(4) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C16 C21 C20 119.0(4) . . ?
C16 C21 H21 120.5 . . ?
C20 C21 H21 120.5 . . ?
C12 C11 C10 119.6(4) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C21 C16 C17 121.2(3) . . ?
C21 C16 N5 118.8(3) . . ?
C17 C16 N5 119.9(3) . . ?
C18 C17 C16 118.6(4) . . ?
C18 C17 H17 120.7 . . ?
C16 C17 H17 120.7 . . ?
C1 O15 H15 106(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
C14 C2 C1 O15 86.0(3) . . . . ?
S3 C2 C1 O15 -149.1(2) . . . . ?
C14 C2 C1 N5 -156.7(2) . . . . ?
S3 C2 C1 N5 -31.8(3) . . . . ?
C14 C2 C1 C7 -38.4(4) . . . . ?
S3 C2 C1 C7 86.5(3) . . . . ?
N5 C4 S3 C2 -11.0(2) . . . . ?
S6 C4 S3 C2 169.45(19) . . . . ?
C14 C2 S3 C4 151.3(2) . . . . ?
C1 C2 S3 C4 25.4(2) . . . . ?
S6 C4 N5 C16 2.8(4) . . . . ?
S3 C4 N5 C16 -176.7(2) . . . . ?
S6 C4 N5 C1 171.5(2) . . . . ?
S3 C4 N5 C1 -8.0(3) . . . . ?
O15 C1 N5 C4 141.8(2) . . . . ?
C2 C1 N5 C4 27.3(3) . . . . ?
C7 C1 N5 C4 -93.1(3) . . . . ?
O15 C1 N5 C16 -49.0(3) . . . . ?
C2 C1 N5 C16 -163.6(2) . . . . ?
C7 C1 N5 C16 76.1(3) . . . . ?
C1 C2 C14 C13 -168.4(3) . . . . ?
S3 C2 C14 C13 71.4(4) . . . . ?
C1 C2 C14 C9 9.3(4) . . . . ?
S3 C2 C14 C9 -110.9(3) . . . . ?
C9 C14 C13 C12 0.9(6) . . . . ?
C2 C14 C13 C12 178.7(4) . . . . ?
C9 C8 C7 C1 -48.8(4) . . . . ?
O15 C1 C7 C8 -62.0(4) . . . . ?
N5 C1 C7 C8 174.6(3) . . . . ?
C2 C1 C7 C8 58.6(4) . . . . ?
C14 C13 C12 C11 -0.2(7) . . . . ?
C13 C14 C9 C10 0.0(5) . . . . ?
C2 C14 C9 C10 -177.6(3) . . . . ?
C13 C14 C9 C8 177.6(3) . . . . ?
C2 C14 C9 C8 -0.1(5) . . . . ?
C11 C10 C9 C14 -1.8(6) . . . . ?
C11 C10 C9 C8 -179.4(4) . . . . ?
C7 C8 C9 C14 20.4(5) . . . . ?
C7 C8 C9 C10 -162.1(3) . . . . ?
C17 C18 C19 C20 0.2(7) . . . . ?
C18 C19 C20 C21 -0.8(7) . . . . ?
C19 C20 C21 C16 0.7(6) . . . . ?
C13 C12 C11 C10 -1.5(7) . . . . ?
C9 C10 C11 C12 2.5(7) . . . . ?
C20 C21 C16 C17 0.1(5) . . . . ?
C20 C21 C16 N5 -177.1(4) . . . . ?
C4 N5 C16 C21 -108.0(3) . . . . ?
C1 N5 C16 C21 83.5(4) . . . . ?
C4 N5 C16 C17 74.7(4) . . . . ?
C1 N5 C16 C17 -93.8(4) . . . . ?
C19 C18 C17 C16 0.5(6) . . . . ?
C21 C16 C17 C18 -0.6(5) . . . . ?
N5 C16 C17 C18 176.5(3) . . . . ?

_refine_diff_density_max         0.180
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.037




####################################################################### 
# 
# 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_LA037TF
_database_code_depnum_ccdc_archive 'CCDC 2375946'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2024-08-06 deposited with the CCDC.	2024-10-28 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT902_LA037TF             
;
PROBLEM: No (Interpretable) Reflections Found in FCF ....     Please Check
RESPONSE: Cif file generated through Olex2 using DISCAMBtaam refinement and well-interpreted by check on-line
;
# Added during the CSD deposition process: Tuesday 06 August 2024 08:59 AM
# end Validation Reply Form

_audit_creation_date             2024-08-06
_audit_creation_method           
;
Olex2 1.5-ac6-019
(compiled 2024.02.14 svn.r2f8d729c for Rigaku Oxford Diffraction, GUI svn.r6920)
;
_chemical_name_systematic        
;
'8-methoxy-3-phenyl-4,5-dihydronaphtho[2,1-d]thiazole-2(3H)-thione'
;
_chemical_formula_moiety         'C18 H15 N O S2'
_chemical_formula_sum            'C18 H15 N O S2'
_chemical_formula_weight         325.458
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00313 0.00162 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.01085 0.00610 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
S 0.12485 0.12449 'NoSpherA2: Chem.Sci. 2021, DOI:10.1039/D0SC05526C'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_symmetry_Int_Tables_number      14
_cell_length_a                   11.1398(10)
_cell_length_b                   14.0582(10)
_cell_length_c                   10.5753(9)
_cell_angle_alpha                90
_cell_angle_beta                 106.341(9)
_cell_angle_gamma                90
_cell_volume                     1589.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5823
_cell_measurement_theta_min      2.4780
_cell_measurement_theta_max      27.5050
_exptl_absorpt_coefficient_mu    0.335
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_F_000             680
_exptl_crystal_description       'rectangular plate'
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.364
_exptl_crystal_size_mid          0.099
_exptl_crystal_size_min          0.047
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 1 -5 0.1774
-1 5 0 0.0531
1 -5 0 0.0398
-2 0 5 0.1723
-5 -1 0 0.0224
5 1 0 0.0243
1 -5 1 0.0408
_exptl_absorpt_correction_T_min  0.799
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.43.130a (Rigaku Oxford Diffraction, 2024)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_reflns_av_R_equivalents  0.0401
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_Laue_measured_fraction_full 0.9983
_diffrn_reflns_Laue_measured_fraction_max 0.9470
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            21360
_diffrn_reflns_point_group_measured_fraction_full 0.9983
_diffrn_reflns_point_group_measured_fraction_max 0.9470
_diffrn_reflns_theta_full        25.2417
_diffrn_reflns_theta_max         28.70
_diffrn_reflns_theta_min         2.48
_diffrn_measured_fraction_theta_full 0.9983
_diffrn_measured_fraction_theta_max 0.9470
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC12 (RINC): Kappa single'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 5.8140
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              -14
_reflns_limit_k_max              18
_reflns_limit_k_min              0
_reflns_limit_l_max              14
_reflns_limit_l_min              0
_reflns_number_gt                2882
_reflns_number_total             3884
_reflns_threshold_expression     I>=2u(I)
_computing_molecular_graphics    'Olex2 1.5-ac6-019 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac6-019 (Dolomanov et al., 2009)'
_computing_structure_refinement  
'olex2.refine 1.5-ac6-019 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.2253
_refine_diff_density_min         -0.2040
_refine_diff_density_rms         0.0559
_refine_ls_d_res_high            0.7400
_refine_ls_d_res_low             8.2283
_refine_ls_goodness_of_fit_ref   1.0354
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     334
_refine_ls_number_reflns         3881
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0491
_refine_ls_R_factor_gt           0.0281
_refine_ls_restrained_S_all      1.0354
_refine_ls_shift/su_max          0.0006
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0119P)²+0.1361P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0492
_refine_ls_wR_factor_ref         0.0537
_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
;
_olex2_refine_details            
;
Refinement using NoSpherA2, an implementation of
NOn-SPHERical Atom-form-factors in Olex2.
Please cite:
F. Kleemiss et al. Chem. Sci. DOI 10.1039/D0SC05526C - 2021
NoSpherA2 implementation of HAR makes use of
tailor-made aspherical atomic form factors calculated
on-the-fly from a Hirshfeld-partitioned electron density (ED) - not from
spherical-atom form factors.

The ED is calculated from a gaussian basis set single determinant SCF
wavefunction - either Hartree-Fock or DFT using selected funtionals
 - for a fragment of the crystal.
This fragment can be embedded in an electrostatic crystal field by employing 
cluster charges
or modelled using implicit solvation models, depending on the software used.
The following options were used:
   SOFTWARE:       discambMATTS
   PARTITIONING:   NoSpherA2
   INT ACCURACY:   Normal
   METHOD:         B3LYP
   BASIS SET:      def2-SVP
   CHARGE:         0
   MULTIPLICITY:   1
   DATE:           2024-08-06_09-37-35
;
_atom_sites_solution_primary     dual
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_refinement_flags_posn
S3 S 0.46532(3) 0.609668(18) 0.55749(3) 0.04557(8) Uani 1.000000 .
S5 S 0.23601(3) 0.58048(2) 0.33173(3) 0.05587(10) Uani 1.000000 .
N4 N 0.32661(8) 0.74695(6) 0.45199(8) 0.0405(2) Uani 1.000000 .
O15 O 0.81029(9) 0.63493(6) 1.02620(9) 0.0673(3) Uani 1.000000 .
C17 C 0.22666(10) 0.80239(7) 0.36969(10) 0.0418(2) Uani 1.000000 .
C2 C 0.50391(10) 0.72282(7) 0.62136(10) 0.0389(2) Uani 1.000000 .
C7 C 0.42604(14) 0.89009(9) 0.58856(15) 0.0500(3) Uani 1.000000 .
H7A H 0.3586(14) 0.9016(10) 0.6451(16) 0.081(5) Uani 1.000000 .
H7B H 0.3917(15) 0.9339(10) 0.5014(15) 0.079(5) Uani 1.000000 .
C1 C 0.42100(10) 0.78716(7) 0.55250(10) 0.0387(2) Uani 1.000000 .
C4 C 0.33413(10) 0.65044(8) 0.43947(10) 0.0428(2) Uani 1.000000 .
C14 C 0.60047(10) 0.74681(7) 0.74119(10) 0.0398(2) Uani 1.000000 .
C8 C 0.55883(16) 0.91661(9) 0.66564(15) 0.0550(3) Uani 1.000000 .
H8A H 0.6173(16) 0.9184(11) 0.5947(18) 0.098(6) Uani 1.000000 .
H8B H 0.5615(15) 0.9850(12) 0.7103(14) 0.094(5) Uani 1.000000 .
C9 C 0.62144(11) 0.84436(7) 0.76891(11) 0.0446(3) Uani 1.000000 .
C13 C 0.66572(11) 0.67858(8) 0.82867(12) 0.0463(3) Uani 1.000000 .
H13 H 0.6513(13) 0.6049(10) 0.8077(13) 0.079(5) Uani 1.000000 .
C22 C 0.23057(13) 0.82697(9) 0.24492(12) 0.0502(3) Uani 1.000000 .
H22 H 0.3086(14) 0.8019(12) 0.2131(14) 0.100(6) Uani 1.000000 .
C11 C 0.76993(13) 0.80257(9) 0.97717(13) 0.0555(3) Uani 1.000000 .
H11 H 0.8353(15) 0.8244(11) 1.0706(15) 0.102(6) Uani 1.000000 .
C12 C 0.75143(11) 0.70631(8) 0.94685(11) 0.0494(3) Uani 1.000000 .
C18 C 0.13067(14) 0.83297(11) 0.41862(15) 0.0644(4) Uani 1.000000 .
H18 H 0.1319(16) 0.8106(13) 0.5171(16) 0.119(7) Uani 1.000000 .
C10 C 0.70525(13) 0.87002(9) 0.88734(13) 0.0551(3) Uani 1.000000 .
H10 H 0.7210(15) 0.9444(10) 0.9110(14) 0.091(5) Uani 1.000000 .
C21 C 0.13642(15) 0.88354(10) 0.16690(14) 0.0596(3) Uani 1.000000 .
H21 H 0.1364(17) 0.9029(13) 0.0709(15) 0.114(6) Uani 1.000000 .
C20 C 0.04004(14) 0.91446(10) 0.21405(15) 0.0617(4) Uani 1.000000 .
H20 H -0.0326(15) 0.9585(11) 0.1553(15) 0.099(6) Uani 1.000000 .
C16 C 0.8977(2) 0.66037(17) 1.1470(2) 0.0743(5) Uani 1.000000 .
H16A H 0.968(2) 0.6984(16) 1.1290(19) 0.111(7) Uani 1.000000 .
H16B H 0.931(3) 0.5917(17) 1.190(3) 0.177(13) Uani 1.000000 .
H16C H 0.858(2) 0.695(2) 1.212(2) 0.147(11) Uani 1.000000 .
C19 C 0.03671(15) 0.88951(12) 0.33978(18) 0.0742(4) Uani 1.000000 .
H19 H -0.0367(16) 0.9142(12) 0.3755(18) 0.109(6) Uani 1.000000 .


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S3 C2 1.7344(10) . ?
S3 C4 1.7308(11) . ?
S5 C4 1.6610(11) . ?
N4 C17 1.4350(13) . ?
N4 C1 1.3878(13) . ?
N4 C4 1.3681(14) . ?
O15 C12 1.3534(14) . ?
O15 C16 1.417(2) . ?
C17 C22 1.3765(16) . ?
C17 C18 1.3811(17) . ?
C2 C1 1.3502(14) . ?
C2 C14 1.4524(14) . ?
C7 H7A 1.096(16) . ?
C7 H7B 1.085(15) . ?
C7 C1 1.4934(15) . ?
C7 C8 1.521(2) . ?
C14 C9 1.4081(14) . ?
C14 C13 1.3878(15) . ?
C8 H8A 1.124(19) . ?
C8 H8B 1.067(16) . ?
C8 C9 1.5107(17) . ?
C9 C10 1.3829(17) . ?
C13 H13 1.062(14) . ?
C13 C12 1.3979(17) . ?
C22 H22 1.076(14) . ?
C22 C21 1.3880(18) . ?
C11 H11 1.093(14) . ?
C11 C12 1.3926(17) . ?
C11 C10 1.3913(18) . ?
C18 H18 1.084(15) . ?
C18 C19 1.390(2) . ?
C10 H10 1.077(14) . ?
C21 H21 1.051(15) . ?
C21 C20 1.375(2) . ?
C20 H20 1.069(14) . ?
C20 C19 1.386(2) . ?
C16 H16A 1.01(2) . ?
C16 H16B 1.09(2) . ?
C16 H16C 1.04(3) . ?
C19 H19 1.051(15) . ?

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
C4 S3 C2 92.50(5) . . ?
C1 N4 C17 122.32(9) . . ?
C4 N4 C17 122.55(9) . . ?
C4 N4 C1 115.11(9) . . ?
C16 O15 C12 117.51(13) . . ?
C22 C17 N4 119.30(10) . . ?
C18 C17 N4 119.49(10) . . ?
C18 C17 C22 121.18(12) . . ?
C1 C2 S3 110.33(8) . . ?
C14 C2 S3 126.46(8) . . ?
C14 C2 C1 122.78(9) . . ?
H7B C7 H7A 104.3(11) . . ?
C1 C7 H7A 107.5(8) . . ?
C1 C7 H7B 110.7(7) . . ?
C8 C7 H7A 112.6(8) . . ?
C8 C7 H7B 111.9(8) . . ?
C8 C7 C1 109.60(11) . . ?
C2 C1 N4 113.33(9) . . ?
C7 C1 N4 123.80(10) . . ?
C7 C1 C2 122.71(10) . . ?
S5 C4 S3 123.90(7) . . ?
N4 C4 S3 108.71(8) . . ?
N4 C4 S5 127.39(8) . . ?
C9 C14 C2 116.52(9) . . ?
C13 C14 C2 122.79(9) . . ?
C13 C14 C9 120.61(10) . . ?
H8A C8 C7 107.9(9) . . ?
H8B C8 C7 111.1(8) . . ?
H8B C8 H8A 109.0(12) . . ?
C9 C8 C7 113.84(11) . . ?
C9 C8 H8A 105.1(8) . . ?
C9 C8 H8B 109.6(8) . . ?
C8 C9 C14 119.24(10) . . ?
C10 C9 C14 118.22(11) . . ?
C10 C9 C8 122.42(11) . . ?
H13 C13 C14 121.0(7) . . ?
C12 C13 C14 120.08(11) . . ?
C12 C13 H13 118.9(7) . . ?
H22 C22 C17 117.7(8) . . ?
C21 C22 C17 119.42(13) . . ?
C21 C22 H22 122.9(8) . . ?
C12 C11 H11 119.9(8) . . ?
C10 C11 H11 120.7(8) . . ?
C10 C11 C12 119.37(12) . . ?
C13 C12 O15 115.94(11) . . ?
C11 C12 O15 124.28(11) . . ?
C11 C12 C13 119.77(11) . . ?
H18 C18 C17 117.9(9) . . ?
C19 C18 C17 119.02(13) . . ?
C19 C18 H18 123.1(9) . . ?
C11 C10 C9 121.91(12) . . ?
H10 C10 C9 119.2(8) . . ?
H10 C10 C11 118.9(8) . . ?
H21 C21 C22 121.2(10) . . ?
C20 C21 C22 120.13(14) . . ?
C20 C21 H21 118.7(10) . . ?
H20 C20 C21 120.9(10) . . ?
C19 C20 C21 120.15(14) . . ?
C19 C20 H20 118.9(10) . . ?
H16A C16 O15 109.7(12) . . ?
H16B C16 O15 102.8(12) . . ?
H16B C16 H16A 111.3(18) . . ?
H16C C16 O15 113.6(13) . . ?
H16C C16 H16A 111.9(18) . . ?
H16C C16 H16B 107.1(19) . . ?
C20 C19 C18 120.10(14) . . ?
H19 C19 C18 120.2(10) . . ?
H19 C19 C20 119.7(10) . . ?

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
S3 C2 C1 N4 1.20(8) . . . . ?
S3 C2 C1 C7 176.82(9) . . . . ?
S3 C2 C14 C9 175.52(10) . . . . ?
S3 C2 C14 C13 -7.56(12) . . . . ?
S3 C4 N4 C17 -178.91(7) . . . . ?
S3 C4 N4 C1 -0.54(9) . . . . ?
S5 C4 N4 C17 0.67(12) . . . . ?
S5 C4 N4 C1 179.04(9) . . . . ?
N4 C17 C22 C21 -177.62(11) . . . . ?
N4 C17 C18 C19 177.69(13) . . . . ?
N4 C1 C2 C14 -171.68(8) . . . . ?
N4 C1 C7 C8 -160.25(13) . . . . ?
O15 C12 C13 C14 179.76(10) . . . . ?
O15 C12 C11 C10 179.29(13) . . . . ?
C17 C22 C21 C20 -0.15(15) . . . . ?
C17 C18 C19 C20 0.02(18) . . . . ?
C2 C1 C7 C8 24.60(13) . . . . ?
C2 C14 C9 C8 -9.20(13) . . . . ?
C2 C14 C9 C10 174.77(11) . . . . ?
C2 C14 C13 C12 -175.53(11) . . . . ?
C7 C8 C9 C14 38.20(16) . . . . ?
C7 C8 C9 C10 -145.94(12) . . . . ?
C14 C9 C10 C11 1.17(13) . . . . ?
C14 C13 C12 C11 0.79(15) . . . . ?
C8 C9 C10 C11 -174.73(14) . . . . ?
C9 C10 C11 C12 0.85(16) . . . . ?
C13 C12 C11 C10 -1.84(14) . . . . ?
C22 C21 C20 C19 0.20(17) . . . . ?
C18 C19 C20 C21 -0.1(2) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'

