# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_N11_LT
_database_code_depnum_ccdc_archive 'CCDC 2391532'
loop_
_audit_author_name
_audit_author_address
'Mikhail Grigoriev'
;IPCE RAS
Russia
;
_audit_update_record             
;
2024-10-16 deposited with the CCDC.	2025-05-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H11 N O2 S'
_chemical_formula_weight         257.30

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.3991(11)
_cell_length_b                   11.6602(15)
_cell_length_c                   12.1285(16)
_cell_angle_alpha                90
_cell_angle_beta                 103.325(6)
_cell_angle_gamma                90
_cell_volume                     1155.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1174
_cell_measurement_theta_min      3.20
_cell_measurement_theta_max      20.41

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.271
_shelx_estimated_absorpt_T_min   0.876
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.869
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19713
_diffrn_reflns_av_unetI/netI     0.1623
_diffrn_reflns_av_R_equivalents  0.1270
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.151
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3360
_reflns_number_gt                1821
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0188P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3360
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0513
_refine_ls_wR_factor_ref         0.0859
_refine_ls_wR_factor_gt          0.0756
_refine_ls_goodness_of_fit_ref   0.801
_refine_ls_restrained_S_all      0.801
_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
S1 S 0.52949(7) 0.30543(5) 0.44452(4) 0.01655(15) Uani 1 1 d . . . . .
O1 O 0.56419(18) 0.45020(14) 0.74000(11) 0.0179(4) Uani 1 1 d . . . . .
O2 O 0.21910(19) 0.16048(13) 0.58497(11) 0.0181(4) Uani 1 1 d . . . . .
N2 N 0.3646(2) 0.31368(16) 0.67879(12) 0.0112(4) Uani 1 1 d . . . . .
C1 C 0.5249(3) 0.3566(2) 0.70046(15) 0.0134(5) Uani 1 1 d . . . . .
C3 C 0.3487(3) 0.2079(2) 0.62242(15) 0.0130(5) Uani 1 1 d . . . . .
C3A C 0.5166(3) 0.16832(18) 0.61542(15) 0.0123(5) Uani 1 1 d . . . . .
H3B H 0.547711 0.095978 0.659398 0.015 Uiso 1 1 calc R U . . .
C4 C 0.5345(3) 0.15499(19) 0.49076(16) 0.0129(5) Uani 1 1 d . . . . .
H4A H 0.452164 0.103623 0.441854 0.016 Uiso 1 1 calc R U . . .
C5 C 0.7126(3) 0.1227(2) 0.49916(16) 0.0165(5) Uani 1 1 d . . . . .
H5A H 0.748847 0.050806 0.477385 0.020 Uiso 1 1 calc R U . . .
C6 C 0.8079(3) 0.2077(2) 0.54039(16) 0.0173(5) Uani 1 1 d . . . . .
H6A H 0.923738 0.206649 0.552851 0.021 Uiso 1 1 calc R U . . .
C7 C 0.7084(3) 0.3088(2) 0.56592(15) 0.0134(5) Uani 1 1 d . . . . .
H7A H 0.768046 0.383640 0.578811 0.016 Uiso 1 1 calc R U . . .
C7A C 0.6326(3) 0.26725(18) 0.66470(16) 0.0111(5) Uani 1 1 d . . . . .
H7B H 0.719554 0.240745 0.730689 0.013 Uiso 1 1 calc R U . . .
C8 C 0.2293(3) 0.37861(19) 0.69925(16) 0.0123(5) Uani 1 1 d . . . . .
C9 C 0.1830(3) 0.4784(2) 0.63918(17) 0.0189(6) Uani 1 1 d . . . . .
H9A H 0.238047 0.502045 0.582828 0.023 Uiso 1 1 calc R U . . .
C10 C 0.0560(3) 0.5443(2) 0.66104(19) 0.0249(6) Uani 1 1 d . . . . .
H10A H 0.024630 0.613293 0.620098 0.030 Uiso 1 1 calc R U . . .
C11 C -0.0250(3) 0.5091(2) 0.74286(18) 0.0226(6) Uani 1 1 d . . . . .
H11A H -0.112047 0.553844 0.758011 0.027 Uiso 1 1 calc R U . . .
C12 C 0.0217(3) 0.4087(2) 0.80225(17) 0.0225(6) Uani 1 1 d . . . . .
H12A H -0.033932 0.384504 0.858078 0.027 Uiso 1 1 calc R U . . .
C13 C 0.1489(3) 0.3432(2) 0.78102(16) 0.0176(5) Uani 1 1 d . . . . .
H13A H 0.180750 0.274428 0.822232 0.021 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 C4 1.839(2) . ?
S1 C7 1.846(2) . ?
O1 C1 1.207(3) . ?
O2 C3 1.212(2) . ?
N2 C3 1.402(3) . ?
N2 C1 1.403(3) . ?
N2 C8 1.434(3) . ?
C1 C7A 1.508(3) . ?
C3 C3A 1.505(3) . ?
C3A C7A 1.539(3) . ?
C3A C4 1.561(3) . ?
C3A H3B 1.0000 . ?
C4 C5 1.523(3) . ?
C4 H4A 1.0000 . ?
C5 C6 1.299(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.518(3) . ?
C6 H6A 0.9500 . ?
C7 C7A 1.558(3) . ?
C7 H7A 1.0000 . ?
C7A H7B 1.0000 . ?
C8 C9 1.381(3) . ?
C8 C13 1.385(3) . ?
C9 C10 1.389(3) . ?
C9 H9A 0.9500 . ?
C10 C11 1.388(3) . ?
C10 H10A 0.9500 . ?
C11 C12 1.383(3) . ?
C11 H11A 0.9500 . ?
C12 C13 1.385(3) . ?
C12 H12A 0.9500 . ?
C13 H13A 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
C4 S1 C7 79.64(10) . . ?
C3 N2 C1 112.62(18) . . ?
C3 N2 C8 123.98(19) . . ?
C1 N2 C8 122.93(19) . . ?
O1 C1 N2 124.0(2) . . ?
O1 C1 C7A 127.7(2) . . ?
N2 C1 C7A 108.25(19) . . ?
O2 C3 N2 124.1(2) . . ?
O2 C3 C3A 127.7(2) . . ?
N2 C3 C3A 108.20(19) . . ?
C3 C3A C7A 105.41(17) . . ?
C3 C3A C4 112.70(16) . . ?
C7A C3A C4 104.91(16) . . ?
C3 C3A H3B 111.2 . . ?
C7A C3A H3B 111.2 . . ?
C4 C3A H3B 111.2 . . ?
C5 C4 C3A 105.78(16) . . ?
C5 C4 S1 102.08(15) . . ?
C3A C4 S1 101.52(14) . . ?
C5 C4 H4A 115.2 . . ?
C3A C4 H4A 115.2 . . ?
S1 C4 H4A 115.2 . . ?
C6 C5 C4 110.2(2) . . ?
C6 C5 H5A 124.9 . . ?
C4 C5 H5A 124.9 . . ?
C5 C6 C7 110.6(2) . . ?
C5 C6 H6A 124.7 . . ?
C7 C6 H6A 124.7 . . ?
C6 C7 C7A 104.86(17) . . ?
C6 C7 S1 101.86(14) . . ?
C7A C7 S1 101.83(14) . . ?
C6 C7 H7A 115.5 . . ?
C7A C7 H7A 115.5 . . ?
S1 C7 H7A 115.5 . . ?
C1 C7A C3A 105.17(17) . . ?
C1 C7A C7 112.62(17) . . ?
C3A C7A C7 105.60(15) . . ?
C1 C7A H7B 111.1 . . ?
C3A C7A H7B 111.1 . . ?
C7 C7A H7B 111.1 . . ?
C9 C8 C13 120.3(2) . . ?
C9 C8 N2 119.45(19) . . ?
C13 C8 N2 120.2(2) . . ?
C8 C9 C10 120.1(2) . . ?
C8 C9 H9A 120.0 . . ?
C10 C9 H9A 120.0 . . ?
C11 C10 C9 119.8(2) . . ?
C11 C10 H10A 120.1 . . ?
C9 C10 H10A 120.1 . . ?
C12 C11 C10 119.7(2) . . ?
C12 C11 H11A 120.1 . . ?
C10 C11 H11A 120.1 . . ?
C11 C12 C13 120.6(2) . . ?
C11 C12 H12A 119.7 . . ?
C13 C12 H12A 119.7 . . ?
C12 C13 C8 119.5(2) . . ?
C12 C13 H13A 120.2 . . ?
C8 C13 H13A 120.2 . . ?

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
C3 N2 C1 O1 173.97(18) . . . . ?
C8 N2 C1 O1 1.5(3) . . . . ?
C3 N2 C1 C7A -5.3(2) . . . . ?
C8 N2 C1 C7A -177.76(16) . . . . ?
C1 N2 C3 O2 -172.20(18) . . . . ?
C8 N2 C3 O2 0.2(3) . . . . ?
C1 N2 C3 C3A 6.4(2) . . . . ?
C8 N2 C3 C3A 178.78(17) . . . . ?
O2 C3 C3A C7A 173.79(19) . . . . ?
N2 C3 C3A C7A -4.8(2) . . . . ?
O2 C3 C3A C4 59.9(3) . . . . ?
N2 C3 C3A C4 -118.62(18) . . . . ?
C3 C3A C4 C5 176.30(18) . . . . ?
C7A C3A C4 C5 62.1(2) . . . . ?
C3 C3A C4 S1 70.1(2) . . . . ?
C7A C3A C4 S1 -44.11(18) . . . . ?
C7 S1 C4 C5 -50.12(13) . . . . ?
C7 S1 C4 C3A 59.00(14) . . . . ?
C3A C4 C5 C6 -66.9(2) . . . . ?
S1 C4 C5 C6 38.96(19) . . . . ?
C4 C5 C6 C7 0.2(2) . . . . ?
C5 C6 C7 C7A 66.8(2) . . . . ?
C5 C6 C7 S1 -39.0(2) . . . . ?
C4 S1 C7 C6 50.13(14) . . . . ?
C4 S1 C7 C7A -58.03(14) . . . . ?
O1 C1 C7A C3A -177.27(19) . . . . ?
N2 C1 C7A C3A 2.0(2) . . . . ?
O1 C1 C7A C7 -62.8(3) . . . . ?
N2 C1 C7A C7 116.48(18) . . . . ?
C3 C3A C7A C1 1.7(2) . . . . ?
C4 C3A C7A C1 120.84(17) . . . . ?
C3 C3A C7A C7 -117.65(17) . . . . ?
C4 C3A C7A C7 1.5(2) . . . . ?
C6 C7 C7A C1 -178.67(17) . . . . ?
S1 C7 C7A C1 -72.84(18) . . . . ?
C6 C7 C7A C3A -64.4(2) . . . . ?
S1 C7 C7A C3A 41.41(18) . . . . ?
C3 N2 C8 C9 -108.2(2) . . . . ?
C1 N2 C8 C9 63.3(3) . . . . ?
C3 N2 C8 C13 73.7(2) . . . . ?
C1 N2 C8 C13 -114.8(2) . . . . ?
C13 C8 C9 C10 0.4(3) . . . . ?
N2 C8 C9 C10 -177.7(2) . . . . ?
C8 C9 C10 C11 -0.5(3) . . . . ?
C9 C10 C11 C12 0.1(4) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C11 C12 C13 C8 -0.2(3) . . . . ?
C9 C8 C13 C12 -0.1(3) . . . . ?
N2 C8 C13 C12 178.0(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C3A H3B O1 1.00 2.41 3.249(3) 141.4 2_646 yes
C5 H5A O2 0.95 2.61 3.542(3) 167.2 3_656 yes
C6 H6A O2 0.95 2.48 3.415(3) 168.2 1_655 yes

_refine_diff_density_max         0.596
_refine_diff_density_min         -0.436
_refine_diff_density_rms         0.079

####################################################################### 
# 
# 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_N11_2_LT
_database_code_depnum_ccdc_archive 'CCDC 2391533'
loop_
_audit_author_name
_audit_author_address
'Mikhail Grigoriev'
;IPCE RAS
Russia
;
_audit_update_record             
;
2024-10-16 deposited with the CCDC.	2025-05-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H11 N O2 S'
_chemical_formula_weight         257.30

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.1401(7)
_cell_length_b                   8.0432(6)
_cell_length_c                   15.6461(12)
_cell_angle_alpha                90
_cell_angle_beta                 90.023(3)
_cell_angle_gamma                90
_cell_volume                     1150.23(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2899
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      27.55

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.486
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.273
_shelx_estimated_absorpt_T_min   0.942
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.870
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18622
_diffrn_reflns_av_unetI/netI     0.0516
_diffrn_reflns_av_R_equivalents  0.0601
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.429
_diffrn_reflns_theta_max         29.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3332
_reflns_number_gt                2424
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0374P)²+0.6462P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3332
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0477
_refine_ls_wR_factor_ref         0.1102
_refine_ls_wR_factor_gt          0.0978
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
S1 S 0.77301(9) 1.02006(11) 0.81122(6) 0.0192(3) Uani 0.693(4) 1 d . . P A 1
S1A S 0.56666(19) 0.8017(3) 0.73178(15) 0.0208(7) Uani 0.307(4) 1 d . . P A 2
O1 O 0.81787(14) 0.42371(17) 0.76240(8) 0.0279(3) Uani 1 1 d . . . . .
O2 O 0.79313(13) 0.76353(15) 0.52899(7) 0.0197(3) Uani 1 1 d . . . . .
N2 N 0.80612(14) 0.56298(18) 0.63357(9) 0.0173(3) Uani 1 1 d . . . . .
C1 C 0.82601(18) 0.5514(2) 0.72189(11) 0.0204(4) Uani 1 1 d . . . . .
C3 C 0.81335(17) 0.7252(2) 0.60302(10) 0.0161(3) Uani 1 1 d . . . . .
C3A C 0.84915(18) 0.8396(2) 0.67720(10) 0.0187(3) Uani 1 1 d . . . . .
H3AA H 0.944665 0.897516 0.667997 0.022 Uiso 1 1 calc R U . A 1
C4 C 0.7249(2) 0.9664(2) 0.69750(11) 0.0273(4) Uani 0.693(4) 1 d . . P A 1
H4 H 0.720601 1.063895 0.657890 0.033 Uiso 0.693(4) 1 calc R U P A 1
C5 C 0.5911(3) 0.8764(5) 0.7050(2) 0.0190(6) Uani 0.693(4) 1 d . . P A 1
H5 H 0.509630 0.887180 0.667683 0.023 Uiso 0.693(4) 1 calc R U P A 1
C6 C 0.5974(4) 0.7736(4) 0.7730(3) 0.0205(6) Uani 0.693(4) 1 d . . P A 1
H6 H 0.520934 0.700351 0.789579 0.025 Uiso 0.693(4) 1 calc R U P A 1
C7 C 0.7335(2) 0.7888(3) 0.81690(12) 0.0306(5) Uani 0.693(4) 1 d . . P A 1
H7 H 0.735166 0.740320 0.875751 0.037 Uiso 0.693(4) 1 calc R U P A 1
C4A C 0.7249(2) 0.9664(2) 0.69750(11) 0.0273(4) Uani 0.307(4) 1 d . . P A 2
H4A H 0.697733 1.039752 0.648379 0.033 Uiso 0.307(4) 1 calc R U P A 2
C5A C 0.7416(8) 1.0454(9) 0.7702(6) 0.0231(14) Uani 0.307(4) 1 d . . P A 2
H5A H 0.750739 1.162795 0.773989 0.028 Uiso 0.307(4) 1 calc R U P A 2
C6A C 0.7446(8) 0.9434(10) 0.8403(5) 0.0219(14) Uani 0.307(4) 1 d . . P A 2
H6A H 0.753445 0.980358 0.897696 0.026 Uiso 0.307(4) 1 calc R U P A 2
C7B C 0.7335(2) 0.7888(3) 0.81690(12) 0.0306(5) Uani 0.307(4) 1 d . . P A 2
H7B H 0.713212 0.711744 0.865636 0.037 Uiso 0.307(4) 1 calc R U P A 2
C7A C 0.85595(19) 0.7241(2) 0.75585(10) 0.0208(4) Uani 1 1 d . . . . .
H7AA H 0.954101 0.729755 0.783954 0.025 Uiso 1 1 calc R U . A 1
C8 C 0.76774(17) 0.4224(2) 0.58101(10) 0.0164(3) Uani 1 1 d . . . . .
C9 C 0.62103(18) 0.3890(2) 0.56541(11) 0.0188(4) Uani 1 1 d . . . . .
H9A H 0.546897 0.457365 0.589372 0.023 Uiso 1 1 calc R U . . .
C10 C 0.58427(19) 0.2542(2) 0.51432(11) 0.0215(4) Uani 1 1 d . . . . .
H10A H 0.484337 0.230340 0.502992 0.026 Uiso 1 1 calc R U . . .
C11 C 0.69286(19) 0.1543(2) 0.47972(11) 0.0221(4) Uani 1 1 d . . . . .
H11A H 0.667110 0.062096 0.444850 0.027 Uiso 1 1 calc R U . . .
C12 C 0.83927(19) 0.1888(2) 0.49600(11) 0.0216(4) Uani 1 1 d . . . . .
H12A H 0.913371 0.119780 0.472447 0.026 Uiso 1 1 calc R U . . .
C13 C 0.87749(18) 0.3238(2) 0.54660(11) 0.0194(4) Uani 1 1 d . . . . .
H13A H 0.977436 0.348289 0.557523 0.023 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 C4 1.883(2) . ?
S1 C7 1.897(2) . ?
S1A C7B 2.027(3) . ?
S1A C4A 2.034(3) . ?
O1 C1 1.209(2) . ?
O2 C3 1.2128(19) . ?
N2 C3 1.391(2) . ?
N2 C1 1.397(2) . ?
N2 C8 1.441(2) . ?
C1 C7A 1.512(3) . ?
C3 C3A 1.517(2) . ?
C3A C7A 1.543(2) . ?
C3A C4 1.559(2) . ?
C3A C4A 1.559(2) . ?
C3A H3AA 1.0000 . ?
C4 C5 1.427(4) . ?
C4 H4 1.0000 . ?
C5 C6 1.349(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.426(4) . ?
C6 H6 0.9500 . ?
C7 C7A 1.561(2) . ?
C7 H7 1.0000 . ?
C4A C5A 1.312(9) . ?
C4A H4A 1.0000 . ?
C5A C6A 1.368(14) . ?
C5A H5A 0.9500 . ?
C6A C7B 1.300(8) . ?
C6A H6A 0.9500 . ?
C7B C7A 1.561(2) . ?
C7B H7B 1.0000 . ?
C7A H7AA 1.0000 . ?
C8 C13 1.388(2) . ?
C8 C9 1.389(2) . ?
C9 C10 1.388(2) . ?
C9 H9A 0.9500 . ?
C10 C11 1.387(2) . ?
C10 H10A 0.9500 . ?
C11 C12 1.390(2) . ?
C11 H11A 0.9500 . ?
C12 C13 1.388(2) . ?
C12 H12A 0.9500 . ?
C13 H13A 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
C4 S1 C7 77.01(9) . . ?
C7B S1A C4A 70.83(10) . . ?
C3 N2 C1 113.36(14) . . ?
C3 N2 C8 123.45(14) . . ?
C1 N2 C8 122.93(15) . . ?
O1 C1 N2 124.57(17) . . ?
O1 C1 C7A 127.39(16) . . ?
N2 C1 C7A 108.04(14) . . ?
O2 C3 N2 124.03(15) . . ?
O2 C3 C3A 127.53(16) . . ?
N2 C3 C3A 108.45(14) . . ?
C3 C3A C7A 104.67(14) . . ?
C3 C3A C4 113.33(14) . . ?
C7A C3A C4 105.12(13) . . ?
C3 C3A C4A 113.33(14) . . ?
C7A C3A C4A 105.12(13) . . ?
C3 C3A H3AA 111.1 . . ?
C7A C3A H3AA 111.1 . . ?
C4 C3A H3AA 111.1 . . ?
C5 C4 C3A 108.00(19) . . ?
C5 C4 S1 103.78(16) . . ?
C3A C4 S1 99.94(12) . . ?
C5 C4 H4 114.5 . . ?
C3A C4 H4 114.5 . . ?
S1 C4 H4 114.5 . . ?
C6 C5 C4 109.9(2) . . ?
C6 C5 H5 125.1 . . ?
C4 C5 H5 125.1 . . ?
C5 C6 C7 111.4(2) . . ?
C5 C6 H6 124.3 . . ?
C7 C6 H6 124.3 . . ?
C6 C7 C7A 107.59(18) . . ?
C6 C7 S1 103.17(18) . . ?
C7A C7 S1 99.32(13) . . ?
C6 C7 H7 115.0 . . ?
C7A C7 H7 115.0 . . ?
S1 C7 H7 115.0 . . ?
C5A C4A C3A 114.1(4) . . ?
C5A C4A S1A 99.7(3) . . ?
C3A C4A S1A 98.37(13) . . ?
C5A C4A H4A 114.2 . . ?
C3A C4A H4A 114.2 . . ?
S1A C4A H4A 114.2 . . ?
C4A C5A C6A 114.0(6) . . ?
C4A C5A H5A 123.0 . . ?
C6A C5A H5A 123.0 . . ?
C7B C6A C5A 110.3(6) . . ?
C7B C6A H6A 124.9 . . ?
C5A C6A H6A 124.9 . . ?
C6A C7B C7A 115.8(4) . . ?
C6A C7B S1A 101.2(3) . . ?
C7A C7B S1A 98.88(12) . . ?
C6A C7B H7B 113.1 . . ?
C7A C7B H7B 113.1 . . ?
S1A C7B H7B 113.1 . . ?
C1 C7A C3A 105.42(14) . . ?
C1 C7A C7B 113.06(16) . . ?
C3A C7A C7B 104.97(13) . . ?
C1 C7A C7 113.06(16) . . ?
C3A C7A C7 104.97(13) . . ?
C1 C7A H7AA 111.0 . . ?
C3A C7A H7AA 111.0 . . ?
C7 C7A H7AA 111.0 . . ?
C13 C8 C9 121.25(16) . . ?
C13 C8 N2 119.60(14) . . ?
C9 C8 N2 119.14(15) . . ?
C10 C9 C8 119.07(16) . . ?
C10 C9 H9A 120.5 . . ?
C8 C9 H9A 120.5 . . ?
C11 C10 C9 120.28(16) . . ?
C11 C10 H10A 119.9 . . ?
C9 C10 H10A 119.9 . . ?
C10 C11 C12 120.10(17) . . ?
C10 C11 H11A 119.9 . . ?
C12 C11 H11A 119.9 . . ?
C13 C12 C11 120.17(16) . . ?
C13 C12 H12A 119.9 . . ?
C11 C12 H12A 119.9 . . ?
C8 C13 C12 119.12(16) . . ?
C8 C13 H13A 120.4 . . ?
C12 C13 H13A 120.4 . . ?

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
C3 N2 C1 O1 176.71(16) . . . . ?
C8 N2 C1 O1 2.4(3) . . . . ?
C3 N2 C1 C7A -2.33(18) . . . . ?
C8 N2 C1 C7A -176.60(14) . . . . ?
C1 N2 C3 O2 -176.86(15) . . . . ?
C8 N2 C3 O2 -2.6(2) . . . . ?
C1 N2 C3 C3A 2.88(18) . . . . ?
C8 N2 C3 C3A 177.11(13) . . . . ?
O2 C3 C3A C7A 177.58(15) . . . . ?
N2 C3 C3A C7A -2.15(17) . . . . ?
O2 C3 C3A C4 63.6(2) . . . . ?
N2 C3 C3A C4 -116.13(15) . . . . ?
O2 C3 C3A C4A 63.6(2) . . . . ?
N2 C3 C3A C4A -116.13(15) . . . . ?
C3 C3A C4 C5 50.8(2) . . . . ?
C7A C3A C4 C5 -62.9(2) . . . . ?
C3 C3A C4 S1 158.92(12) . . . . ?
C7A C3A C4 S1 45.21(16) . . . . ?
C7 S1 C4 C5 49.75(17) . . . . ?
C7 S1 C4 C3A -61.73(12) . . . . ?
C3A C4 C5 C6 65.1(3) . . . . ?
S1 C4 C5 C6 -40.4(2) . . . . ?
C4 C5 C6 C7 1.1(3) . . . . ?
C5 C6 C7 C7A -66.2(3) . . . . ?
C5 C6 C7 S1 38.2(2) . . . . ?
C4 S1 C7 C6 -48.65(16) . . . . ?
C4 S1 C7 C7A 62.01(12) . . . . ?
C3 C3A C4A C5A 168.2(4) . . . . ?
C7A C3A C4A C5A 54.5(4) . . . . ?
C3 C3A C4A S1A 63.57(16) . . . . ?
C7A C3A C4A S1A -50.14(16) . . . . ?
C3A C4A C5A C6A -60.6(6) . . . . ?
S1A C4A C5A C6A 43.2(6) . . . . ?
C4A C5A C6A C7B 1.6(8) . . . . ?
C5A C6A C7B C7A 59.6(6) . . . . ?
C5A C6A C7B S1A -46.0(6) . . . . ?
O1 C1 C7A C3A -178.20(17) . . . . ?
N2 C1 C7A C3A 0.81(18) . . . . ?
O1 C1 C7A C7B -64.1(2) . . . . ?
N2 C1 C7A C7B 114.93(15) . . . . ?
O1 C1 C7A C7 -64.1(2) . . . . ?
N2 C1 C7A C7 114.93(15) . . . . ?
C3 C3A C7A C1 0.79(17) . . . . ?
C4 C3A C7A C1 120.45(15) . . . . ?
C4A C3A C7A C1 120.45(15) . . . . ?
C3 C3A C7A C7B -118.84(15) . . . . ?
C4A C3A C7A C7B 0.82(19) . . . . ?
C3 C3A C7A C7 -118.84(15) . . . . ?
C4 C3A C7A C7 0.82(19) . . . . ?
C6A C7B C7A C1 -172.3(4) . . . . ?
S1A C7B C7A C1 -65.27(16) . . . . ?
C6A C7B C7A C3A -58.0(4) . . . . ?
S1A C7B C7A C3A 49.12(16) . . . . ?
C6 C7 C7A C1 -53.3(2) . . . . ?
S1 C7 C7A C1 -160.40(12) . . . . ?
C6 C7 C7A C3A 61.1(2) . . . . ?
S1 C7 C7A C3A -46.01(15) . . . . ?
C3 N2 C8 C13 97.62(19) . . . . ?
C1 N2 C8 C13 -88.69(19) . . . . ?
C3 N2 C8 C9 -82.0(2) . . . . ?
C1 N2 C8 C9 91.7(2) . . . . ?
C13 C8 C9 C10 -0.1(3) . . . . ?
N2 C8 C9 C10 179.58(15) . . . . ?
C8 C9 C10 C11 0.3(3) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C9 C8 C13 C12 -0.3(3) . . . . ?
N2 C8 C13 C12 -179.94(15) . . . . ?
C11 C12 C13 C8 0.5(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C7^a H7^a O2 1.00 2.46 3.389(2) 155.1 4_576 yes
C5A^b H5A^b O1 0.95 2.19 3.124(7) 166.1 1_565 yes
C3A H3AA^a O1 1.00 2.44 3.257(2) 138.9 2_756 yes

_refine_diff_density_max         0.299
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.062

####################################################################### 
# 
# 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_N11_R3_LT
_database_code_depnum_ccdc_archive 'CCDC 2424425'
loop_
_audit_author_name
_audit_author_address
'Mikhail Grigoriev'
;IPCE RAS
Russia
;
_audit_update_record             
;
2025-02-16 deposited with the CCDC.	2025-05-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H11 N O2 S'
_chemical_formula_weight         257.30

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      trigonal
_space_group_IT_number           146
_space_group_name_H-M_alt        'R 3 :H'
_space_group_name_Hall           'R 3'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'

_cell_length_a                   17.5842(13)
_cell_length_b                   17.5842(13)
_cell_length_c                   9.8889(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     2648.0(4)
_cell_formula_units_Z            9
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3062
_cell_measurement_theta_min      2.46
_cell_measurement_theta_max      27.91

_exptl_crystal_description       bulk
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_F_000             1206
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.360
_exptl_crystal_size_min          0.340
_exptl_absorpt_coefficient_mu    0.267
_shelx_estimated_absorpt_T_min   0.901
_shelx_estimated_absorpt_T_max   0.915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6874
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15223
_diffrn_reflns_av_unetI/netI     0.0632
_diffrn_reflns_av_R_equivalents  0.0567
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.014
_diffrn_reflns_theta_max         30.103
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3410
_reflns_number_gt                3025
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.983
_reflns_Friedel_fraction_max     0.980
_reflns_Friedel_fraction_full    0.993

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0351P)²+0.4277P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1246 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.07(5)
_chemical_absolute_configuration AD
_refine_ls_number_reflns         3410
_refine_ls_number_parameters     163
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0484
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.0801
_refine_ls_wR_factor_gt          0.0766
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.013
_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
S1 S 0.44290(4) 0.66271(4) 0.30215(6) 0.01302(14) Uani 1 1 d . . . . .
O1 O 0.54645(13) 0.61493(13) 0.61606(19) 0.0164(4) Uani 1 1 d . . . . .
O2 O 0.29655(13) 0.41828(12) 0.39504(19) 0.0162(4) Uani 1 1 d . . . . .
N2 N 0.41182(14) 0.51080(14) 0.5334(2) 0.0112(4) Uani 1 1 d . . . . .
C1 C 0.50075(17) 0.57330(17) 0.5218(3) 0.0118(5) Uani 1 1 d . . . . .
C3 C 0.37344(17) 0.47298(17) 0.4094(2) 0.0109(5) Uani 1 1 d . . . . .
C3A C 0.44343(17) 0.51266(16) 0.3003(3) 0.0111(5) Uani 1 1 d . . . . .
H3AA H 0.451775 0.466972 0.253389 0.013 Uiso 1 1 calc R U . . .
C4 C 0.42330(18) 0.56812(18) 0.1980(3) 0.0124(5) Uani 1 1 d . . . . .
H4A H 0.364360 0.536156 0.153669 0.015 Uiso 1 1 calc R U . . .
C5 C 0.50116(19) 0.60838(19) 0.1021(3) 0.0156(6) Uani 1 1 d . . . . .
H5A H 0.498742 0.593870 0.009089 0.019 Uiso 1 1 calc R U . . .
C6 C 0.57306(19) 0.66672(19) 0.1667(3) 0.0160(6) Uani 1 1 d . . . . .
H6A H 0.629518 0.700248 0.126911 0.019 Uiso 1 1 calc R U . . .
C7A C 0.52749(17) 0.58014(17) 0.3752(3) 0.0109(5) Uani 1 1 d . . . . .
H7AA H 0.576400 0.567298 0.362749 0.013 Uiso 1 1 calc R U . . .
C7 C 0.55117(18) 0.67168(18) 0.3146(3) 0.0131(5) Uani 1 1 d . . . . .
H7A H 0.596444 0.723802 0.365706 0.016 Uiso 1 1 calc R U . . .
C8 C 0.36367(17) 0.49579(17) 0.6569(3) 0.0118(5) Uani 1 1 d . . . . .
C9 C 0.29899(18) 0.51881(19) 0.6649(3) 0.0152(5) Uani 1 1 d . . . . .
H9A H 0.285492 0.542611 0.588421 0.018 Uiso 1 1 calc R U . . .
C10 C 0.25409(18) 0.50667(19) 0.7860(3) 0.0170(6) Uani 1 1 d . . . . .
H10A H 0.209653 0.522198 0.792407 0.020 Uiso 1 1 calc R U . . .
C11 C 0.27402(18) 0.47200(19) 0.8973(3) 0.0167(6) Uani 1 1 d . . . . .
H11A H 0.243048 0.463632 0.979724 0.020 Uiso 1 1 calc R U . . .
C12 C 0.33939(18) 0.44935(19) 0.8887(3) 0.0160(6) Uani 1 1 d . . . . .
H12A H 0.352906 0.425592 0.965217 0.019 Uiso 1 1 calc R U . . .
C13 C 0.38469(18) 0.46152(18) 0.7684(3) 0.0140(5) Uani 1 1 d . . . . .
H13A H 0.429586 0.446617 0.762136 0.017 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 C7 1.834(3) . ?
S1 C4 1.836(3) . ?
O1 C1 1.209(3) . ?
O2 C3 1.213(3) . ?
N2 C1 1.396(3) . ?
N2 C3 1.398(3) . ?
N2 C8 1.434(3) . ?
C1 C7A 1.511(4) . ?
C3 C3A 1.519(4) . ?
C3A C7A 1.545(4) . ?
C3A C4 1.563(4) . ?
C3A H3AA 1.0000 . ?
C4 C5 1.519(4) . ?
C4 H4A 1.0000 . ?
C5 C6 1.327(4) . ?
C5 H5A 0.9500 . ?
C6 C7 1.526(4) . ?
C6 H6A 0.9500 . ?
C7A C7 1.566(4) . ?
C7A H7AA 1.0000 . ?
C7 H7A 1.0000 . ?
C8 C9 1.387(4) . ?
C8 C13 1.392(4) . ?
C9 C10 1.391(4) . ?
C9 H9A 0.9500 . ?
C10 C11 1.385(4) . ?
C10 H10A 0.9500 . ?
C11 C12 1.395(4) . ?
C11 H11A 0.9500 . ?
C12 C13 1.388(4) . ?
C12 H12A 0.9500 . ?
C13 H13A 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
C7 S1 C4 80.33(13) . . ?
C1 N2 C3 112.8(2) . . ?
C1 N2 C8 122.7(2) . . ?
C3 N2 C8 124.1(2) . . ?
O1 C1 N2 123.9(2) . . ?
O1 C1 C7A 127.3(2) . . ?
N2 C1 C7A 108.8(2) . . ?
O2 C3 N2 124.1(2) . . ?
O2 C3 C3A 127.4(2) . . ?
N2 C3 C3A 108.5(2) . . ?
C3 C3A C7A 104.9(2) . . ?
C3 C3A C4 111.2(2) . . ?
C7A C3A C4 105.0(2) . . ?
C3 C3A H3AA 111.8 . . ?
C7A C3A H3AA 111.8 . . ?
C4 C3A H3AA 111.8 . . ?
C5 C4 C3A 105.2(2) . . ?
C5 C4 S1 102.17(18) . . ?
C3A C4 S1 101.76(17) . . ?
C5 C4 H4A 115.3 . . ?
C3A C4 H4A 115.3 . . ?
S1 C4 H4A 115.3 . . ?
C6 C5 C4 110.4(2) . . ?
C6 C5 H5A 124.8 . . ?
C4 C5 H5A 124.8 . . ?
C5 C6 C7 109.6(2) . . ?
C5 C6 H6A 125.2 . . ?
C7 C6 H6A 125.2 . . ?
C1 C7A C3A 105.0(2) . . ?
C1 C7A C7 111.2(2) . . ?
C3A C7A C7 105.5(2) . . ?
C1 C7A H7AA 111.6 . . ?
C3A C7A H7AA 111.6 . . ?
C7 C7A H7AA 111.6 . . ?
C6 C7 C7A 104.7(2) . . ?
C6 C7 S1 102.22(18) . . ?
C7A C7 S1 101.89(17) . . ?
C6 C7 H7A 115.4 . . ?
C7A C7 H7A 115.4 . . ?
S1 C7 H7A 115.4 . . ?
C9 C8 C13 121.0(2) . . ?
C9 C8 N2 119.3(2) . . ?
C13 C8 N2 119.6(2) . . ?
C8 C9 C10 119.3(3) . . ?
C8 C9 H9A 120.4 . . ?
C10 C9 H9A 120.4 . . ?
C11 C10 C9 120.2(3) . . ?
C11 C10 H10A 119.9 . . ?
C9 C10 H10A 119.9 . . ?
C10 C11 C12 120.2(3) . . ?
C10 C11 H11A 119.9 . . ?
C12 C11 H11A 119.9 . . ?
C13 C12 C11 120.0(3) . . ?
C13 C12 H12A 120.0 . . ?
C11 C12 H12A 120.0 . . ?
C12 C13 C8 119.3(3) . . ?
C12 C13 H13A 120.3 . . ?
C8 C13 H13A 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
C3 N2 C1 O1 179.0(2) . . . . ?
C8 N2 C1 O1 6.2(4) . . . . ?
C3 N2 C1 C7A 0.1(3) . . . . ?
C8 N2 C1 C7A -172.7(2) . . . . ?
C1 N2 C3 O2 -178.7(2) . . . . ?
C8 N2 C3 O2 -6.0(4) . . . . ?
C1 N2 C3 C3A 0.7(3) . . . . ?
C8 N2 C3 C3A 173.4(2) . . . . ?
O2 C3 C3A C7A 178.2(3) . . . . ?
N2 C3 C3A C7A -1.2(3) . . . . ?
O2 C3 C3A C4 65.2(3) . . . . ?
N2 C3 C3A C4 -114.2(2) . . . . ?
C3 C3A C4 C5 176.1(2) . . . . ?
C7A C3A C4 C5 63.2(2) . . . . ?
C3 C3A C4 S1 69.9(2) . . . . ?
C7A C3A C4 S1 -43.0(2) . . . . ?
C7 S1 C4 C5 -50.11(18) . . . . ?
C7 S1 C4 C3A 58.49(17) . . . . ?
C3A C4 C5 C6 -67.5(3) . . . . ?
S1 C4 C5 C6 38.4(3) . . . . ?
C4 C5 C6 C7 0.3(3) . . . . ?
O1 C1 C7A C3A -179.7(3) . . . . ?
N2 C1 C7A C3A -0.8(3) . . . . ?
O1 C1 C7A C7 -66.1(3) . . . . ?
N2 C1 C7A C7 112.8(2) . . . . ?
C3 C3A C7A C1 1.2(3) . . . . ?
C4 C3A C7A C1 118.5(2) . . . . ?
C3 C3A C7A C7 -116.3(2) . . . . ?
C4 C3A C7A C7 1.0(3) . . . . ?
C5 C6 C7 C7A 67.0(3) . . . . ?
C5 C6 C7 S1 -38.9(3) . . . . ?
C1 C7A C7 C6 -178.0(2) . . . . ?
C3A C7A C7 C6 -64.7(2) . . . . ?
C1 C7A C7 S1 -71.8(2) . . . . ?
C3A C7A C7 S1 41.5(2) . . . . ?
C4 S1 C7 C6 50.32(18) . . . . ?
C4 S1 C7 C7A -57.75(17) . . . . ?
C1 N2 C8 C9 111.6(3) . . . . ?
C3 N2 C8 C9 -60.4(3) . . . . ?
C1 N2 C8 C13 -66.0(3) . . . . ?
C3 N2 C8 C13 122.0(3) . . . . ?
C13 C8 C9 C10 -0.5(4) . . . . ?
N2 C8 C9 C10 -178.1(2) . . . . ?
C8 C9 C10 C11 0.0(4) . . . . ?
C9 C10 C11 C12 0.2(4) . . . . ?
C10 C11 C12 C13 0.0(4) . . . . ?
C11 C12 C13 C8 -0.5(4) . . . . ?
C9 C8 C13 C12 0.7(4) . . . . ?
N2 C8 C13 C12 178.3(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C3A H3AA O2 1.00 2.57 3.522(3) 159.4 9_554 yes
C6 H6A O1 0.95 2.45 3.344(3) 155.9 6_564 yes
C7A H7AA O1 1.00 2.41 3.338(3) 154.3 8_654 yes

_refine_diff_density_max         0.258
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_N11_3_LT
_database_code_depnum_ccdc_archive 'CCDC 2391534'
loop_
_audit_author_name
_audit_author_address
'Mikhail Grigoriev'
;IPCE RAS
Russia
;
_audit_update_record             
;
2024-10-16 deposited with the CCDC.	2025-05-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H11 N O2 S'
_chemical_formula_weight         257.30

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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.7276(12)
_cell_length_b                   6.3628(7)
_cell_length_c                   17.390(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.131(4)
_cell_angle_gamma                90
_cell_volume                     1185.2(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1978
_cell_measurement_theta_min      3.41
_cell_measurement_theta_max      23.45

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.265
_shelx_estimated_absorpt_T_min   0.901
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.919
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  
'Bruker KAPPA APEX II area-detector diffractometer'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19969
_diffrn_reflns_av_unetI/netI     0.0796
_diffrn_reflns_av_R_equivalents  0.0913
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.725
_diffrn_reflns_theta_max         29.979
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3440
_reflns_number_gt                2131
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0390P)²+0.5508P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3440
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1087
_refine_ls_R_factor_gt           0.0542
_refine_ls_wR_factor_ref         0.1218
_refine_ls_wR_factor_gt          0.1012
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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
S1 S 0.67669(9) 0.14127(18) 0.31536(7) 0.0217(5) Uani 0.715(6) 1 d . . P A 1
S1A S 0.5937(3) 0.4845(6) 0.3944(2) 0.0321(14) Uani 0.285(6) 1 d . . P A 2
O1 O 0.30808(14) 0.1647(2) 0.46605(8) 0.0231(3) Uani 1 1 d . . . . .
O2 O 0.31396(14) 0.5779(2) 0.25189(9) 0.0285(4) Uani 1 1 d . . . . .
N2 N 0.28658(15) 0.3932(2) 0.36355(9) 0.0138(3) Uani 1 1 d . . . . .
C1 C 0.34112(18) 0.2270(3) 0.40445(12) 0.0160(4) Uani 1 1 d . . . . .
C3 C 0.34433(19) 0.4360(3) 0.29522(11) 0.0173(4) Uani 1 1 d . . . . .
C3A C 0.44826(18) 0.2791(3) 0.28683(12) 0.0175(4) Uani 1 1 d . . . . .
H3A H 0.432181 0.190989 0.239708 0.021 Uiso 1 1 calc R U . A 1
C4 C 0.5807(2) 0.3787(4) 0.28786(14) 0.0262(5) Uani 0.715(6) 1 d . . P A 1
H4A H 0.602144 0.447042 0.238511 0.031 Uiso 0.715(6) 1 calc R U P A 1
C4A C 0.5807(2) 0.3787(4) 0.28786(14) 0.0262(5) Uani 0.285(6) 1 d . . P A 2
H4B H 0.588843 0.491269 0.248316 0.031 Uiso 0.285(6) 1 calc R U P A 2
C5 C 0.5960(4) 0.5106(8) 0.3549(4) 0.0296(11) Uani 0.715(6) 1 d . . P A 1
H5A H 0.605453 0.659004 0.353855 0.035 Uiso 0.715(6) 1 calc R U P A 1
C6 C 0.5950(4) 0.3923(9) 0.4197(3) 0.0285(11) Uani 0.715(6) 1 d . . P A 1
H6A H 0.603560 0.446560 0.470604 0.034 Uiso 0.715(6) 1 calc R U P A 1
C7 C 0.5793(2) 0.1733(4) 0.40084(13) 0.0288(5) Uani 0.715(6) 1 d . . P A 1
H7 H 0.599574 0.073852 0.444262 0.035 Uiso 0.715(6) 1 calc R U P A 1
C5A C 0.6736(10) 0.231(3) 0.2875(8) 0.032(2) Uani 0.285(6) 1 d . . P A 2
H5B H 0.729018 0.210377 0.247349 0.039 Uiso 0.285(6) 1 calc R U P A 2
C6A C 0.6735(10) 0.1164(17) 0.3542(9) 0.029(2) Uani 0.285(6) 1 d . . P A 2
H6B H 0.732438 0.008804 0.366992 0.035 Uiso 0.285(6) 1 calc R U P A 2
C7B C 0.5793(2) 0.1733(4) 0.40084(13) 0.0288(5) Uani 0.285(6) 1 d . . P A 2
H7B H 0.588005 0.115241 0.454296 0.035 Uiso 0.285(6) 1 calc R U P A 2
C7A C 0.44755(18) 0.1436(3) 0.35986(11) 0.0179(4) Uani 1 1 d . . . . .
H7A H 0.433209 -0.007429 0.346121 0.021 Uiso 1 1 calc R U . A 1
C8 C 0.17580(18) 0.5010(3) 0.38576(11) 0.0145(4) Uani 1 1 d . . . . .
C9 C 0.18478(19) 0.7030(3) 0.41482(11) 0.0179(4) Uani 1 1 d . . . . .
H9A H 0.263784 0.769753 0.421963 0.021 Uiso 1 1 calc R U . . .
C10 C 0.0765(2) 0.8072(3) 0.43345(12) 0.0213(5) Uani 1 1 d . . . . .
H10A H 0.081292 0.946376 0.453149 0.026 Uiso 1 1 calc R U . . .
C11 C -0.0384(2) 0.7087(3) 0.42340(12) 0.0222(5) Uani 1 1 d . . . . .
H11A H -0.112013 0.780189 0.436509 0.027 Uiso 1 1 calc R U . . .
C12 C -0.0463(2) 0.5050(3) 0.39411(12) 0.0211(5) Uani 1 1 d . . . . .
H12A H -0.125146 0.437705 0.387191 0.025 Uiso 1 1 calc R U . . .
C13 C 0.06156(19) 0.4008(3) 0.37505(12) 0.0180(4) Uani 1 1 d . . . . .
H13A H 0.056986 0.262081 0.354870 0.022 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 C7 1.874(2) . ?
S1 C4 1.876(2) . ?
S1A C4A 1.969(4) . ?
S1A C7B 1.989(5) . ?
O1 C1 1.213(2) . ?
O2 C3 1.209(2) . ?
N2 C1 1.386(2) . ?
N2 C3 1.397(2) . ?
N2 C8 1.443(2) . ?
C1 C7A 1.511(3) . ?
C3 C3A 1.510(3) . ?
C3A C7A 1.535(3) . ?
C3A C4 1.555(3) . ?
C3A C4A 1.555(3) . ?
C3A H3A 1.0000 . ?
C4 C5 1.438(6) . ?
C4 H4A 1.0000 . ?
C4A C5A 1.372(15) . ?
C4A H4B 1.0000 . ?
C5 C6 1.356(10) . ?
C5 H5A 0.9500 . ?
C6 C7 1.439(6) . ?
C6 H6A 0.9500 . ?
C7 C7A 1.559(3) . ?
C7 H7 1.0000 . ?
C5A C6A 1.37(3) . ?
C5A H5B 0.9500 . ?
C6A C7B 1.379(13) . ?
C6A H6B 0.9500 . ?
C7B C7A 1.559(3) . ?
C7B H7B 1.0000 . ?
C7A H7A 1.0000 . ?
C8 C9 1.383(3) . ?
C8 C13 1.385(3) . ?
C9 C10 1.391(3) . ?
C9 H9A 0.9500 . ?
C10 C11 1.385(3) . ?
C10 H10A 0.9500 . ?
C11 C12 1.393(3) . ?
C11 H11A 0.9500 . ?
C12 C13 1.389(3) . ?
C12 H12A 0.9500 . ?
C13 H13A 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
C7 S1 C4 78.03(10) . . ?
C4A S1A C7B 73.21(15) . . ?
C1 N2 C3 113.01(16) . . ?
C1 N2 C8 123.79(15) . . ?
C3 N2 C8 123.03(16) . . ?
O1 C1 N2 124.54(18) . . ?
O1 C1 C7A 127.14(18) . . ?
N2 C1 C7A 108.32(16) . . ?
O2 C3 N2 123.98(18) . . ?
O2 C3 C3A 127.50(18) . . ?
N2 C3 C3A 108.52(16) . . ?
C3 C3A C7A 104.73(15) . . ?
C3 C3A C4 114.11(17) . . ?
C7A C3A C4 105.38(16) . . ?
C3 C3A C4A 114.11(17) . . ?
C7A C3A C4A 105.38(16) . . ?
C3 C3A H3A 110.8 . . ?
C7A C3A H3A 110.8 . . ?
C4 C3A H3A 110.8 . . ?
C5 C4 C3A 108.1(2) . . ?
C5 C4 S1 103.1(3) . . ?
C3A C4 S1 99.39(14) . . ?
C5 C4 H4A 114.8 . . ?
C3A C4 H4A 114.8 . . ?
S1 C4 H4A 114.8 . . ?
C5A C4A C3A 112.5(5) . . ?
C5A C4A S1A 103.0(5) . . ?
C3A C4A S1A 99.66(16) . . ?
C5A C4A H4B 113.5 . . ?
C3A C4A H4B 113.5 . . ?
S1A C4A H4B 113.5 . . ?
C6 C5 C4 110.1(4) . . ?
C6 C5 H5A 124.9 . . ?
C4 C5 H5A 124.9 . . ?
C5 C6 C7 110.7(4) . . ?
C5 C6 H6A 124.6 . . ?
C7 C6 H6A 124.6 . . ?
C6 C7 C7A 108.3(2) . . ?
C6 C7 S1 102.9(3) . . ?
C7A C7 S1 98.92(14) . . ?
C6 C7 H7 115.0 . . ?
C7A C7 H7 115.0 . . ?
S1 C7 H7 115.0 . . ?
C6A C5A C4A 109.1(9) . . ?
C6A C5A H5B 125.5 . . ?
C4A C5A H5B 125.5 . . ?
C5A C6A C7B 113.2(10) . . ?
C5A C6A H6B 123.4 . . ?
C7B C6A H6B 123.4 . . ?
C6A C7B C7A 112.0(6) . . ?
C6A C7B S1A 99.6(5) . . ?
C7A C7B S1A 99.56(17) . . ?
C6A C7B H7B 114.6 . . ?
C7A C7B H7B 114.6 . . ?
S1A C7B H7B 114.6 . . ?
C1 C7A C3A 105.38(15) . . ?
C1 C7A C7B 114.48(17) . . ?
C3A C7A C7B 105.34(16) . . ?
C1 C7A C7 114.48(17) . . ?
C3A C7A C7 105.34(16) . . ?
C1 C7A H7A 110.5 . . ?
C3A C7A H7A 110.5 . . ?
C7 C7A H7A 110.5 . . ?
C9 C8 C13 121.37(18) . . ?
C9 C8 N2 119.86(18) . . ?
C13 C8 N2 118.73(17) . . ?
C8 C9 C10 119.05(19) . . ?
C8 C9 H9A 120.5 . . ?
C10 C9 H9A 120.5 . . ?
C11 C10 C9 120.24(19) . . ?
C11 C10 H10A 119.9 . . ?
C9 C10 H10A 119.9 . . ?
C10 C11 C12 120.20(19) . . ?
C10 C11 H11A 119.9 . . ?
C12 C11 H11A 119.9 . . ?
C13 C12 C11 119.8(2) . . ?
C13 C12 H12A 120.1 . . ?
C11 C12 H12A 120.1 . . ?
C8 C13 C12 119.36(19) . . ?
C8 C13 H13A 120.3 . . ?
C12 C13 H13A 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
C3 N2 C1 O1 178.54(19) . . . . ?
C8 N2 C1 O1 -6.0(3) . . . . ?
C3 N2 C1 C7A -0.5(2) . . . . ?
C8 N2 C1 C7A 175.00(17) . . . . ?
C1 N2 C3 O2 -177.9(2) . . . . ?
C8 N2 C3 O2 6.6(3) . . . . ?
C1 N2 C3 C3A 1.5(2) . . . . ?
C8 N2 C3 C3A -173.99(17) . . . . ?
O2 C3 C3A C7A 177.5(2) . . . . ?
N2 C3 C3A C7A -1.9(2) . . . . ?
O2 C3 C3A C4 62.8(3) . . . . ?
N2 C3 C3A C4 -116.60(19) . . . . ?
O2 C3 C3A C4A 62.8(3) . . . . ?
N2 C3 C3A C4A -116.60(19) . . . . ?
C3 C3A C4 C5 51.6(3) . . . . ?
C7A C3A C4 C5 -62.7(3) . . . . ?
C3 C3A C4 S1 158.79(15) . . . . ?
C7A C3A C4 S1 44.45(18) . . . . ?
C7 S1 C4 C5 49.8(2) . . . . ?
C7 S1 C4 C3A -61.45(15) . . . . ?
C3 C3A C4A C5A 174.2(6) . . . . ?
C7A C3A C4A C5A 59.9(6) . . . . ?
C3 C3A C4A S1A 65.7(2) . . . . ?
C7A C3A C4A S1A -48.7(2) . . . . ?
C3A C4 C5 C6 65.3(4) . . . . ?
S1 C4 C5 C6 -39.3(4) . . . . ?
C4 C5 C6 C7 0.1(6) . . . . ?
C5 C6 C7 C7A -65.0(4) . . . . ?
C5 C6 C7 S1 39.1(4) . . . . ?
C4 S1 C7 C6 -49.5(2) . . . . ?
C4 S1 C7 C7A 61.71(14) . . . . ?
C3A C4A C5A C6A -64.6(9) . . . . ?
S1A C4A C5A C6A 41.8(9) . . . . ?
C4A C5A C6A C7B 2.6(13) . . . . ?
C5A C6A C7B C7A 59.9(10) . . . . ?
C5A C6A C7B S1A -44.6(10) . . . . ?
O1 C1 C7A C3A -179.7(2) . . . . ?
N2 C1 C7A C3A -0.7(2) . . . . ?
O1 C1 C7A C7B -64.5(3) . . . . ?
N2 C1 C7A C7B 114.52(19) . . . . ?
O1 C1 C7A C7 -64.5(3) . . . . ?
N2 C1 C7A C7 114.52(19) . . . . ?
C3 C3A C7A C1 1.6(2) . . . . ?
C4 C3A C7A C1 122.24(17) . . . . ?
C4A C3A C7A C1 122.24(17) . . . . ?
C3 C3A C7A C7B -119.85(18) . . . . ?
C4A C3A C7A C7B 0.8(2) . . . . ?
C3 C3A C7A C7 -119.85(18) . . . . ?
C4 C3A C7A C7 0.8(2) . . . . ?
C6A C7B C7A C1 -173.2(5) . . . . ?
S1A C7B C7A C1 -68.7(2) . . . . ?
C6A C7B C7A C3A -57.9(6) . . . . ?
S1A C7B C7A C3A 46.6(2) . . . . ?
C6 C7 C7A C1 -54.3(3) . . . . ?
S1 C7 C7A C1 -161.08(14) . . . . ?
C6 C7 C7A C3A 61.0(3) . . . . ?
S1 C7 C7A C3A -45.80(18) . . . . ?
C1 N2 C8 C9 108.3(2) . . . . ?
C3 N2 C8 C9 -76.7(2) . . . . ?
C1 N2 C8 C13 -73.8(2) . . . . ?
C3 N2 C8 C13 101.3(2) . . . . ?
C13 C8 C9 C10 -0.1(3) . . . . ?
N2 C8 C9 C10 177.81(18) . . . . ?
C8 C9 C10 C11 0.4(3) . . . . ?
C9 C10 C11 C12 -0.4(3) . . . . ?
C10 C11 C12 C13 0.1(3) . . . . ?
C9 C8 C13 C12 -0.2(3) . . . . ?
N2 C8 C13 C12 -178.16(17) . . . . ?
C11 C12 C13 C8 0.2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C7^a H7^a O1 1.00 2.36 3.337(3) 166.9 3_656 yes
C7B^b H7B^b O1 1.00 2.48 3.337(3) 143.1 3_656 yes

_refine_diff_density_max         0.388
_refine_diff_density_min         -0.348
_refine_diff_density_rms         0.073

