# Supplementary Information (SI) for RSC Advances.
# 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 
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data_shp-9
_database_code_depnum_ccdc_archive 'CCDC 2312181'
loop_
_audit_author_name
_audit_author_address
'Patricia Delgado-Martinez'
;Universidad Complutense de Madrid
Spain
;
_audit_update_record             
;
2023-12-05 deposited with the CCDC.	2024-08-29 downloaded from the CCDC.
;
_audit_creation_date             2023-12-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '1.333(C17 H14 N2 O S)'
_chemical_formula_sum            'C22.67 H18.67 N2.67 O1.33 S1.33'
_chemical_formula_weight         392.48
_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 0.0033 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'

_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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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'
'-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                   19.262(3)
_cell_length_b                   4.9631(9)
_cell_length_c                   30.819(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.509(3)
_cell_angle_gamma                90
_cell_volume                     2913.8(9)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    2243
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.0921
_cell_measurement_theta_min      2.3478
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.222
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.576010
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) was 0.0507 before and 0.0352 after correction. The Ratio of minimum to maximum transmission is 0.5760. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1232
_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0849
_diffrn_reflns_av_unetI/netI     0.0951
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.913
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            13672
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.913
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.944
_diffrn_reflns_theta_min         1.336
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1877
_reflns_number_total             3533
_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       'SAINT v6.28A (Bruker, 2002)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v6.28A (Bruker, 2002)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-1997  (Sheldrick, 2008)'
_refine_diff_density_max         0.288
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     233
_refine_ls_number_reflns         3533
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1173
_refine_ls_R_factor_gt           0.0580
_refine_ls_restrained_S_all      0.967
_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)+(0.0731P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1336
_refine_ls_wR_factor_ref         0.1535
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(C15A)=Sof(H15A)=Sof(C16A)=Sof(H16A)=Sof(H17A)=Sof(C18A)=Sof(H18A)=
 Sof(C19A)=Sof(H19A)=1-FVAR(1)
 Sof(C15)=Sof(H15)=Sof(C16)=Sof(H16)=Sof(H17)=Sof(C18)=Sof(H18)=Sof(C19)=
 Sof(H19)=FVAR(1)
3.a Aromatic/amide H refined with riding coordinates:
 N6(H6), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15), C15A(H15A),
 C16(H16), C16A(H16A), C17(H17), C17(H17A), C18(H18), C18A(H18A), C19(H19),
 C19A(H19A)
3.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.22151(4) 0.10275(16) 0.12386(2) 0.0399(2) Uani 1 1 d . . . . .
O1 O 0.07266(13) 0.6480(6) 0.10463(7) 0.0812(9) Uani 1 1 d . . . . .
N3 N 0.20159(11) 0.1932(5) 0.20335(7) 0.0331(5) Uani 1 1 d . . . . .
N6 N 0.28790(11) -0.1315(5) 0.19897(7) 0.0373(6) Uani 1 1 d . . . . .
H6 H 0.2836 -0.1765 0.2254 0.045 Uiso 1 1 calc R U . . .
C2 C 0.24017(13) 0.0511(5) 0.17979(8) 0.0295(6) Uani 1 1 d . . . . .
C4 C 0.15408(13) 0.3494(5) 0.17705(8) 0.0334(6) Uani 1 1 d . . . . .
C5 C 0.15697(14) 0.3301(6) 0.13277(8) 0.0342(7) Uani 1 1 d . . . . .
C7 C 0.34347(13) -0.2571(6) 0.18156(8) 0.0316(6) Uani 1 1 d . . . . .
C8 C 0.36839(16) -0.1748(7) 0.14423(10) 0.0573(10) Uani 1 1 d . . . . .
H8 H 0.3469 -0.0315 0.1280 0.116(16) Uiso 1 1 calc R . . . .
C9 C 0.42514(17) -0.3024(8) 0.13039(11) 0.0598(10) Uani 1 1 d . . . . .
H9 H 0.4403 -0.2480 0.1045 0.082(12) Uiso 1 1 calc R . . . .
C10 C 0.45860(17) -0.5039(7) 0.15397(11) 0.0580(10) Uani 1 1 d . . . . .
H10 H 0.4982 -0.5830 0.1455 0.134(18) Uiso 1 1 calc R . . . .
C11 C 0.43306(19) -0.5909(8) 0.19098(12) 0.0699(11) Uani 1 1 d . . . . .
H11 H 0.4545 -0.7355 0.2069 0.067(10) Uiso 1 1 calc R . . . .
C12 C 0.37673(16) -0.4678(6) 0.20473(10) 0.0500(8) Uani 1 1 d . . . . .
H12 H 0.3608 -0.5277 0.2301 0.055(9) Uiso 1 1 calc R . . . .
C13 C 0.11429(15) 0.4783(6) 0.09715(9) 0.0397(7) Uani 1 1 d . . . . .
C14 C 0.12157(14) 0.4092(6) 0.05066(9) 0.0369(7) Uani 1 1 d . . . . .
C15 C 0.1007(3) 0.1615(13) 0.03580(19) 0.0442(17) Uani 0.505(4) 1 d . . P A 1
H15 H 0.0859 0.0351 0.0548 0.053 Uiso 0.505(4) 1 calc R U P A 1
C15A C 0.1883(3) 0.4191(13) 0.03483(18) 0.0431(17) Uani 0.495(4) 1 d . . P A 2
H15A H 0.2284 0.4626 0.0542 0.052 Uiso 0.495(4) 1 calc R U P A 2
C16 C 0.1015(3) 0.0975(15) -0.0079(2) 0.0538(19) Uani 0.505(4) 1 d . . P A 1
H16 H 0.0850 -0.0687 -0.0189 0.065 Uiso 0.505(4) 1 calc R U P A 1
C16A C 0.1939(4) 0.3664(14) -0.0077(2) 0.057(2) Uani 0.495(4) 1 d . . P A 2
H16A H 0.2367 0.3754 -0.0181 0.068 Uiso 0.495(4) 1 calc R U P A 2
C17 C 0.1285(2) 0.2942(8) -0.03633(11) 0.0655(11) Uani 1 1 d . . . . .
H17 H 0.1358 0.2496 -0.0646 0.079 Uiso 0.505(4) 1 calc R U P A 1
H17A H 0.1308 0.2535 -0.0655 0.079 Uiso 0.495(4) 1 calc R U P A 2
C18 C 0.1423(4) 0.5410(15) -0.0200(2) 0.059(2) Uani 0.505(4) 1 d . . P A 1
H18 H 0.1540 0.6753 -0.0387 0.071 Uiso 0.505(4) 1 calc R U P A 1
C18A C 0.0706(4) 0.2848(15) -0.0235(2) 0.0539(19) Uani 0.495(4) 1 d . . P A 2
H18A H 0.0310 0.2383 -0.0432 0.065 Uiso 0.495(4) 1 calc R U P A 2
C19 C 0.1400(3) 0.6067(13) 0.0238(2) 0.0473(17) Uani 0.505(4) 1 d . . P A 1
H19 H 0.1506 0.7797 0.0343 0.057 Uiso 0.505(4) 1 calc R U P A 1
C19A C 0.0640(3) 0.3427(13) 0.01980(19) 0.0450(17) Uani 0.495(4) 1 d . . P A 2
H19A H 0.0198 0.3368 0.0284 0.054 Uiso 0.495(4) 1 calc R U P A 2
C20 C 0.10491(16) 0.5209(7) 0.19824(10) 0.0506(9) Uani 1 1 d . . . . .
H20A H 0.1124 0.4898 0.2293 0.076 Uiso 1 1 calc R U . . .
H20B H 0.0574 0.4759 0.1865 0.076 Uiso 1 1 calc R U . . .
H20C H 0.1134 0.7073 0.1925 0.076 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 C2 1.727(3) . ?
S1 C5 1.731(3) . ?
O1 C13 1.209(3) . ?
N3 C2 1.318(3) . ?
N3 C4 1.370(3) . ?
N6 H6 0.8600 . ?
N6 C2 1.362(3) . ?
N6 C7 1.412(3) . ?
C4 C5 1.377(3) . ?
C4 C20 1.494(4) . ?
C5 C13 1.468(4) . ?
C7 C8 1.373(4) . ?
C7 C12 1.371(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.384(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.344(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.377(4) . ?
C11 H11 0.9300 . ?
C11 C12 1.366(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.500(4) . ?
C14 C15 1.352(7) . ?
C14 C15A 1.441(6) . ?
C14 C19 1.364(7) . ?
C14 C19A 1.389(6) . ?
C15 H15 0.9300 . ?
C15 C16 1.385(8) . ?
C15A H15A 0.9300 . ?
C15A C16A 1.356(8) . ?
C16 H16 0.9300 . ?
C16 C17 1.459(8) . ?
C16A H16A 0.9300 . ?
C16A C17 1.472(8) . ?
C17 H17 0.9300 . ?
C17 H17A 0.9300 . ?
C17 C18 1.336(8) . ?
C17 C18A 1.237(7) . ?
C18 H18 0.9300 . ?
C18 C19 1.396(8) . ?
C18A H18A 0.9300 . ?
C18A C19A 1.390(8) . ?
C19 H19 0.9300 . ?
C19A H19A 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 S1 C5 89.24(12) . . ?
C2 N3 C4 111.0(2) . . ?
C2 N6 H6 115.5 . . ?
C2 N6 C7 129.1(2) . . ?
C7 N6 H6 115.5 . . ?
N3 C2 S1 114.80(19) . . ?
N3 C2 N6 121.1(2) . . ?
N6 C2 S1 124.00(19) . . ?
N3 C4 C5 115.2(2) . . ?
N3 C4 C20 118.4(2) . . ?
C5 C4 C20 126.4(2) . . ?
C4 C5 S1 109.75(19) . . ?
C4 C5 C13 127.3(2) . . ?
C13 C5 S1 123.0(2) . . ?
C8 C7 N6 124.5(3) . . ?
C12 C7 N6 117.5(2) . . ?
C12 C7 C8 118.0(3) . . ?
C7 C8 H8 119.6 . . ?
C7 C8 C9 120.8(3) . . ?
C9 C8 H8 119.6 . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.7(3) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 120.7 . . ?
C9 C10 C11 118.7(3) . . ?
C11 C10 H10 120.7 . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 121.0(3) . . ?
C12 C11 H11 119.5 . . ?
C7 C12 H12 119.6 . . ?
C11 C12 C7 120.7(3) . . ?
C11 C12 H12 119.6 . . ?
O1 C13 C5 121.4(3) . . ?
O1 C13 C14 120.0(2) . . ?
C5 C13 C14 118.6(2) . . ?
C15 C14 C13 117.8(3) . . ?
C15 C14 C19 122.6(4) . . ?
C15A C14 C13 122.0(3) . . ?
C19 C14 C13 119.0(4) . . ?
C19A C14 C13 122.1(3) . . ?
C19A C14 C15A 115.9(4) . . ?
C14 C15 H15 120.3 . . ?
C14 C15 C16 119.5(6) . . ?
C16 C15 H15 120.3 . . ?
C14 C15A H15A 119.2 . . ?
C16A C15A C14 121.6(5) . . ?
C16A C15A H15A 119.2 . . ?
C15 C16 H16 120.4 . . ?
C15 C16 C17 119.2(6) . . ?
C17 C16 H16 120.4 . . ?
C15A C16A H16A 121.9 . . ?
C15A C16A C17 116.3(5) . . ?
C17 C16A H16A 121.9 . . ?
C16 C17 H17 121.4 . . ?
C16A C17 H17A 118.3 . . ?
C18 C17 C16 117.1(5) . . ?
C18 C17 H17 121.4 . . ?
C18A C17 C16A 123.3(5) . . ?
C18A C17 H17A 118.3 . . ?
C17 C18 H18 118.5 . . ?
C17 C18 C19 123.0(6) . . ?
C19 C18 H18 118.5 . . ?
C17 C18A H18A 119.6 . . ?
C17 C18A C19A 120.9(6) . . ?
C19A C18A H18A 119.6 . . ?
C14 C19 C18 117.9(6) . . ?
C14 C19 H19 121.0 . . ?
C18 C19 H19 121.0 . . ?
C14 C19A C18A 122.0(6) . . ?
C14 C19A H19A 119.0 . . ?
C18A C19A H19A 119.0 . . ?
C4 C20 H20A 109.5 . . ?
C4 C20 H20B 109.5 . . ?
C4 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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 C5 C13 O1 -175.3(3) . . . . ?
S1 C5 C13 C14 6.5(4) . . . . ?
O1 C13 C14 C15 -112.4(4) . . . . ?
O1 C13 C14 C15A 125.4(4) . . . . ?
O1 C13 C14 C19 59.1(5) . . . . ?
O1 C13 C14 C19A -51.8(5) . . . . ?
N3 C4 C5 S1 0.7(3) . . . . ?
N3 C4 C5 C13 -178.1(3) . . . . ?
N6 C7 C8 C9 177.2(3) . . . . ?
N6 C7 C12 C11 -176.9(3) . . . . ?
C2 S1 C5 C4 -0.2(2) . . . . ?
C2 S1 C5 C13 178.7(3) . . . . ?
C2 N3 C4 C5 -1.0(3) . . . . ?
C2 N3 C4 C20 178.9(2) . . . . ?
C2 N6 C7 C8 14.0(5) . . . . ?
C2 N6 C7 C12 -169.1(3) . . . . ?
C4 N3 C2 S1 0.8(3) . . . . ?
C4 N3 C2 N6 -175.8(2) . . . . ?
C4 C5 C13 O1 3.4(5) . . . . ?
C4 C5 C13 C14 -174.7(3) . . . . ?
C5 S1 C2 N3 -0.3(2) . . . . ?
C5 S1 C2 N6 176.1(2) . . . . ?
C5 C13 C14 C15 65.7(5) . . . . ?
C5 C13 C14 C15A -56.4(5) . . . . ?
C5 C13 C14 C19 -122.7(4) . . . . ?
C5 C13 C14 C19A 126.3(4) . . . . ?
C7 N6 C2 S1 19.0(4) . . . . ?
C7 N6 C2 N3 -164.8(3) . . . . ?
C7 C8 C9 C10 -2.2(6) . . . . ?
C8 C7 C12 C11 0.2(5) . . . . ?
C8 C9 C10 C11 3.4(6) . . . . ?
C9 C10 C11 C12 -2.9(6) . . . . ?
C10 C11 C12 C7 1.1(6) . . . . ?
C12 C7 C8 C9 0.4(5) . . . . ?
C13 C14 C15 C16 175.1(5) . . . . ?
C13 C14 C15A C16A -177.4(5) . . . . ?
C13 C14 C19 C18 -176.2(5) . . . . ?
C13 C14 C19A C18A 178.5(5) . . . . ?
C14 C15 C16 C17 3.3(9) . . . . ?
C14 C15A C16A C17 -1.1(9) . . . . ?
C15 C14 C19 C18 -5.1(8) . . . . ?
C15 C16 C17 C18 -8.9(9) . . . . ?
C15A C14 C19A C18A 1.1(8) . . . . ?
C15A C16A C17 C18A 1.2(9) . . . . ?
C16 C17 C18 C19 7.8(10) . . . . ?
C16A C17 C18A C19A -0.2(11) . . . . ?
C17 C18 C19 C14 -1.1(10) . . . . ?
C17 C18A C19A C14 -1.0(11) . . . . ?
C19 C14 C15 C16 3.8(8) . . . . ?
C19A C14 C15A C16A 0.0(8) . . . . ?
C20 C4 C5 S1 -179.2(2) . . . . ?
C20 C4 C5 C13 2.0(5) . . . . ?

_olex2_submission_original_sample_id 'shp 9'
_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_data1t
_database_code_depnum_ccdc_archive 'CCDC 2312182'
loop_
_audit_author_name
_audit_author_address
'Patricia Delgado-Martinez'
;Universidad Complutense de Madrid
Spain
;
_audit_update_record             
;
2023-12-05 deposited with the CCDC.	2024-08-29 downloaded from the CCDC.
;
_audit_creation_date             2023-12-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H15 Cl N2 O2 S'
_chemical_formula_sum            'C18 H15 Cl N2 O2 S'
_chemical_formula_weight         358.83
_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 0.0033 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'
Cl Cl 0.1484 0.1585 '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'

_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                   9.4627(10)
_cell_length_b                   9.6608(10)
_cell_length_c                   11.0027(11)
_cell_angle_alpha                107.810(2)
_cell_angle_beta                 110.578(2)
_cell_angle_gamma                96.950(2)
_cell_volume                     866.57(16)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2344
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      23.9914
_cell_measurement_theta_min      2.2908
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.353
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.844934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) was 0.0442 before and 0.0203 after correction. The Ratio of minimum to maximum transmission is 0.8449. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0525
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.892
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            9152
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.090
_diffrn_reflns_theta_min         2.133
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.892
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2063
_reflns_number_total             4133
_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       'SAINT v6.28A (Bruker, 2002)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v6.28A (Bruker, 2002)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.247
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         4133
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0994
_refine_ls_R_factor_gt           0.0480
_refine_ls_restrained_S_all      0.970
_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)+(0.0580P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1115
_refine_ls_wR_factor_ref         0.1292
_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:
 C5(H5), C9(H9), C10(H10), C12(H12), C13(H13), C15(H15), C16(H16), C18(H18),
 C19(H19)
2.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
Cl1 Cl -0.04027(8) 0.99298(8) 0.29934(8) 0.0912(3) Uani 1 1 d . . . . .
S1 S 0.34999(8) 0.29215(7) 0.43359(7) 0.0704(2) Uani 1 1 d . . . . .
O1 O 0.4530(2) 0.43501(19) 0.70206(17) 0.0744(5) Uani 1 1 d . . . . .
O2 O 0.43855(19) 0.97092(19) 1.20358(16) 0.0741(5) Uani 1 1 d . . . . .
N3 N 0.1966(2) 0.4615(2) 0.33596(19) 0.0586(5) Uani 1 1 d . . . . .
N6 N 0.2944(2) 0.5533(2) 0.57975(18) 0.0551(5) Uani 1 1 d . . . . .
C2 C 0.2787(2) 0.4506(2) 0.4618(2) 0.0547(6) Uani 1 1 d . . . . .
C4 C 0.1877(3) 0.3433(3) 0.2180(3) 0.0706(7) Uani 1 1 d . . . . .
C5 C 0.2639(3) 0.2456(3) 0.2556(3) 0.0771(7) Uani 1 1 d . . . . .
H5 H 0.2699 0.1602 0.1915 0.093 Uiso 1 1 calc R U . . .
C7 C 0.3859(3) 0.5379(3) 0.6995(2) 0.0563(6) Uani 1 1 d . . . . .
C8 C 0.4010(3) 0.6531(2) 0.8317(2) 0.0533(5) Uani 1 1 d . . . . .
C9 C 0.5065(3) 0.6596(3) 0.9586(3) 0.0687(7) Uani 1 1 d . . . . .
H9 H 0.5684 0.5919 0.9594 0.082 Uiso 1 1 calc R U . . .
C10 C 0.5233(3) 0.7631(3) 1.0846(3) 0.0700(7) Uani 1 1 d . . . . .
H10 H 0.5960 0.7652 1.1685 0.084 Uiso 1 1 calc R U . . .
C11 C 0.4315(3) 0.8632(3) 1.0849(2) 0.0591(6) Uani 1 1 d . . . . .
C12 C 0.3246(3) 0.8594(3) 0.9591(3) 0.0668(7) Uani 1 1 d . . . . .
H12 H 0.2624 0.9269 0.9590 0.080 Uiso 1 1 calc R U . . .
C13 C 0.3098(3) 0.7567(3) 0.8345(2) 0.0618(6) Uani 1 1 d . . . . .
H13 H 0.2380 0.7560 0.7508 0.074 Uiso 1 1 calc R U . . .
C14 C 0.1392(2) 0.5913(3) 0.3285(2) 0.0529(5) Uani 1 1 d . . . . .
C15 C 0.0095(3) 0.6103(3) 0.3548(2) 0.0662(7) Uani 1 1 d . . . . .
H15 H -0.0402 0.5402 0.3786 0.079 Uiso 1 1 calc R U . . .
C16 C -0.0465(3) 0.7337(3) 0.3458(3) 0.0699(7) Uani 1 1 d . . . . .
H16 H -0.1347 0.7469 0.3623 0.084 Uiso 1 1 calc R U . . .
C17 C 0.0296(3) 0.8371(3) 0.3120(2) 0.0600(6) Uani 1 1 d . . . . .
C18 C 0.1607(3) 0.8198(3) 0.2878(2) 0.0633(6) Uani 1 1 d . . . . .
H18 H 0.2115 0.8908 0.2657 0.076 Uiso 1 1 calc R U . . .
C19 C 0.2160(3) 0.6958(3) 0.2967(2) 0.0612(6) Uani 1 1 d . . . . .
H19 H 0.3049 0.6830 0.2812 0.073 Uiso 1 1 calc R U . . .
C20 C 0.0988(4) 0.3395(3) 0.0746(3) 0.0998(10) Uani 1 1 d . . . . .
H20A H -0.0047 0.3479 0.0634 0.150 Uiso 1 1 calc R U . . .
H20B H 0.0928 0.2463 0.0063 0.150 Uiso 1 1 calc R U . . .
H20C H 0.1510 0.4219 0.0616 0.150 Uiso 1 1 calc R U . . .
C21 C 0.5628(3) 0.9951(3) 1.3340(3) 0.0869(8) Uani 1 1 d . . . . .
H21A H 0.6610 1.0165 1.3274 0.130 Uiso 1 1 calc R U . . .
H21B H 0.5518 0.9064 1.3557 0.130 Uiso 1 1 calc R U . . .
H21C H 0.5592 1.0786 1.4066 0.130 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
Cl1 C17 1.741(2) . ?
S1 C2 1.732(2) . ?
S1 C5 1.718(3) . ?
O1 C7 1.245(2) . ?
O2 C11 1.372(3) . ?
O2 C21 1.428(3) . ?
N3 C2 1.373(3) . ?
N3 C4 1.410(3) . ?
N3 C14 1.439(3) . ?
N6 C2 1.316(3) . ?
N6 C7 1.363(3) . ?
C4 C5 1.333(3) . ?
C4 C20 1.491(3) . ?
C5 H5 0.9300 . ?
C7 C8 1.483(3) . ?
C8 C9 1.379(3) . ?
C8 C13 1.399(3) . ?
C9 H9 0.9300 . ?
C9 C10 1.380(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.376(3) . ?
C11 C12 1.384(3) . ?
C12 H12 0.9300 . ?
C12 C13 1.372(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.377(3) . ?
C14 C19 1.373(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.378(3) . ?
C16 H16 0.9300 . ?
C16 C17 1.377(3) . ?
C17 C18 1.376(3) . ?
C18 H18 0.9300 . ?
C18 C19 1.380(3) . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 S1 C2 90.93(12) . . ?
C11 O2 C21 118.1(2) . . ?
C2 N3 C4 114.4(2) . . ?
C2 N3 C14 121.73(18) . . ?
C4 N3 C14 123.6(2) . . ?
C2 N6 C7 115.99(19) . . ?
N3 C2 S1 109.73(16) . . ?
N6 C2 S1 129.95(18) . . ?
N6 C2 N3 120.3(2) . . ?
N3 C4 C20 119.9(2) . . ?
C5 C4 N3 111.2(2) . . ?
C5 C4 C20 128.9(2) . . ?
S1 C5 H5 123.1 . . ?
C4 C5 S1 113.7(2) . . ?
C4 C5 H5 123.1 . . ?
O1 C7 N6 124.0(2) . . ?
O1 C7 C8 120.5(2) . . ?
N6 C7 C8 115.5(2) . . ?
C9 C8 C7 120.0(2) . . ?
C9 C8 C13 117.3(2) . . ?
C13 C8 C7 122.6(2) . . ?
C8 C9 H9 118.8 . . ?
C8 C9 C10 122.3(2) . . ?
C10 C9 H9 118.8 . . ?
C9 C10 H10 120.3 . . ?
C11 C10 C9 119.4(2) . . ?
C11 C10 H10 120.3 . . ?
O2 C11 C10 124.3(2) . . ?
O2 C11 C12 116.1(2) . . ?
C10 C11 C12 119.6(2) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.5(2) . . ?
C13 C12 H12 119.8 . . ?
C8 C13 H13 119.5 . . ?
C12 C13 C8 120.9(2) . . ?
C12 C13 H13 119.5 . . ?
C15 C14 N3 119.8(2) . . ?
C19 C14 N3 119.34(19) . . ?
C19 C14 C15 120.8(2) . . ?
C14 C15 H15 120.2 . . ?
C14 C15 C16 119.6(2) . . ?
C16 C15 H15 120.2 . . ?
C15 C16 H16 120.3 . . ?
C17 C16 C15 119.3(2) . . ?
C17 C16 H16 120.3 . . ?
C16 C17 Cl1 119.80(19) . . ?
C18 C17 Cl1 118.99(18) . . ?
C18 C17 C16 121.2(2) . . ?
C17 C18 H18 120.4 . . ?
C17 C18 C19 119.2(2) . . ?
C19 C18 H18 120.4 . . ?
C14 C19 C18 119.8(2) . . ?
C14 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C4 C20 H20A 109.5 . . ?
C4 C20 H20B 109.5 . . ?
C4 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O2 C21 H21A 109.5 . . ?
O2 C21 H21B 109.5 . . ?
O2 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
Cl1 C17 C18 C19 -179.52(17) . . . . ?
O1 C7 C8 C9 9.0(3) . . . . ?
O1 C7 C8 C13 -169.9(2) . . . . ?
O2 C11 C12 C13 179.4(2) . . . . ?
N3 C4 C5 S1 -0.4(3) . . . . ?
N3 C14 C15 C16 -179.1(2) . . . . ?
N3 C14 C19 C18 179.28(19) . . . . ?
N6 C7 C8 C9 -171.57(19) . . . . ?
N6 C7 C8 C13 9.5(3) . . . . ?
C2 S1 C5 C4 0.9(2) . . . . ?
C2 N3 C4 C5 -0.6(3) . . . . ?
C2 N3 C4 C20 178.6(2) . . . . ?
C2 N3 C14 C15 -75.9(3) . . . . ?
C2 N3 C14 C19 103.4(2) . . . . ?
C2 N6 C7 O1 0.1(3) . . . . ?
C2 N6 C7 C8 -179.24(18) . . . . ?
C4 N3 C2 S1 1.2(2) . . . . ?
C4 N3 C2 N6 -179.41(19) . . . . ?
C4 N3 C14 C15 110.5(2) . . . . ?
C4 N3 C14 C19 -70.2(3) . . . . ?
C5 S1 C2 N3 -1.18(16) . . . . ?
C5 S1 C2 N6 179.5(2) . . . . ?
C7 N6 C2 S1 3.2(3) . . . . ?
C7 N6 C2 N3 -176.05(17) . . . . ?
C7 C8 C9 C10 -179.0(2) . . . . ?
C7 C8 C13 C12 178.5(2) . . . . ?
C8 C9 C10 C11 0.5(4) . . . . ?
C9 C8 C13 C12 -0.5(3) . . . . ?
C9 C10 C11 O2 -179.8(2) . . . . ?
C9 C10 C11 C12 -0.5(4) . . . . ?
C10 C11 C12 C13 0.0(4) . . . . ?
C11 C12 C13 C8 0.5(4) . . . . ?
C13 C8 C9 C10 0.0(3) . . . . ?
C14 N3 C2 S1 -172.88(15) . . . . ?
C14 N3 C2 N6 6.5(3) . . . . ?
C14 N3 C4 C5 173.4(2) . . . . ?
C14 N3 C4 C20 -7.4(3) . . . . ?
C14 C15 C16 C17 -0.7(4) . . . . ?
C15 C14 C19 C18 -1.5(3) . . . . ?
C15 C16 C17 Cl1 179.68(18) . . . . ?
C15 C16 C17 C18 -0.3(4) . . . . ?
C16 C17 C18 C19 0.4(3) . . . . ?
C17 C18 C19 C14 0.4(3) . . . . ?
C19 C14 C15 C16 1.6(3) . . . . ?
C20 C4 C5 S1 -179.4(2) . . . . ?
C21 O2 C11 C10 9.0(3) . . . . ?
C21 O2 C11 C12 -170.4(2) . . . . ?

_olex2_submission_original_sample_id 'sph 53b'
_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_shp-61-pnma
_database_code_depnum_ccdc_archive 'CCDC 2312183'
loop_
_audit_author_name
_audit_author_address
'Patricia Delgado-Martinez'
;Universidad Complutense de Madrid
Spain
;
_audit_update_record             
;
2023-12-05 deposited with the CCDC.	2024-08-29 downloaded from the CCDC.
;
_audit_creation_date             2023-12-04
_audit_creation_method           
;
Olex2 1.5
(compiled 2023.08.24 svn.re1ec1418 for OlexSys, GUI svn.r6817)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H16 N2 O S'
_chemical_formula_sum            'C18 H16 N2 O S'
_chemical_formula_weight         308.39
_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 0.0033 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'

_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           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   20.1281(15)
_cell_length_b                   6.9154(5)
_cell_length_c                   11.3450(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1579.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3343
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.6638
_cell_measurement_theta_min      2.9456
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.208
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.652477
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS v.2.10 (Bruker,2003) was used for absorption correction. R(int) was 0.0418 before and 0.0337 after correction. The Ratio of minimum to maximum transmission is 0.6525. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.09
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0629
_diffrn_reflns_av_unetI/netI     0.0424
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            15926
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.988
_diffrn_reflns_theta_min         2.024
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'Bruker P4'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1232
_reflns_number_total             2163
_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       'SAINT v6.28A (Bruker, 2002)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v6.28A (Bruker, 2002)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2014/7 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-1997  (Sheldrick, 2008)'
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     129
_refine_ls_number_reflns         2163
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0880
_refine_ls_R_factor_gt           0.0441
_refine_ls_restrained_S_all      1.004
_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)+(0.0737P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1198
_refine_ls_wR_factor_ref         0.1377
_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. Others
 Fixed Sof: H20A(0.5) H20B(0.5) H20C(0.5) H21A(0.5) H21B(0.5) H21C(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15), C16(H16)
3.b Idealised Me refined as rotating group:
 C20(H20A,H20B,H20C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.31990(3) 0.2500 0.61031(6) 0.0582(3) Uani 1 2 d S T P . .
O1 O 0.26187(9) 0.2500 0.81966(17) 0.0643(6) Uani 1 2 d S T P . .
N3 N 0.22090(9) 0.2500 0.47106(17) 0.0457(5) Uani 1 2 d S T P . .
N6 N 0.18589(9) 0.2500 0.66684(17) 0.0476(5) Uani 1 2 d S T P . .
C2 C 0.23452(11) 0.2500 0.5887(2) 0.0456(6) Uani 1 2 d S T P . .
C4 C 0.27651(12) 0.2500 0.3970(2) 0.0485(6) Uani 1 2 d S T P . .
C5 C 0.33264(13) 0.2500 0.4597(2) 0.0604(8) Uani 1 2 d S T P . .
H5 H 0.3746 0.2500 0.4255 0.073 Uiso 1 2 calc R U P . .
C7 C 0.20373(12) 0.2500 0.7825(2) 0.0474(6) Uani 1 2 d S T P . .
C8 C 0.14639(13) 0.2500 0.8667(2) 0.0460(6) Uani 1 2 d S T P . .
C9 C 0.15804(15) 0.2500 0.9869(2) 0.0617(8) Uani 1 2 d S T P . .
H9 H 0.2016 0.2500 1.0144 0.074 Uiso 1 2 calc R U P . .
C10 C 0.10674(18) 0.2500 1.0659(3) 0.0790(10) Uani 1 2 d S T P . .
H10 H 0.1154 0.2500 1.1464 0.095 Uiso 1 2 calc R U P . .
C11 C 0.04309(19) 0.2500 1.0260(3) 0.1023(14) Uani 1 2 d S T P . .
H11 H 0.0080 0.2500 1.0794 0.123 Uiso 1 2 calc R U P . .
C12 C 0.03032(18) 0.2500 0.9067(3) 0.1147(17) Uani 1 2 d S T P . .
H12 H -0.0134 0.2500 0.8801 0.138 Uiso 1 2 calc R U P . .
C13 C 0.08159(13) 0.2500 0.8269(3) 0.0689(9) Uani 1 2 d S T P . .
H13 H 0.0727 0.2500 0.7464 0.083 Uiso 1 2 calc R U P . .
C14 C 0.15257(11) 0.2500 0.43044(19) 0.0429(6) Uani 1 2 d S T P . .
C15 C 0.12056(9) 0.0771(3) 0.41219(17) 0.0571(5) Uani 1 1 d . . . . .
H15 H 0.1429 -0.0395 0.4217 0.069 Uiso 1 1 calc R U . . .
C16 C 0.05417(9) 0.0799(3) 0.37927(17) 0.0648(6) Uani 1 1 d . . . . .
H16 H 0.0322 -0.0368 0.3670 0.078 Uiso 1 1 calc R U . . .
C17 C 0.01988(13) 0.2500 0.3643(2) 0.0552(7) Uani 1 2 d S T P . .
C20 C 0.26628(13) 0.2500 0.2661(2) 0.0598(7) Uani 1 2 d S T P . .
H20A H 0.2352 0.1504 0.2452 0.090 Uiso 0.5 1 calc R U P A -1
H20B H 0.3079 0.2263 0.2274 0.090 Uiso 0.5 1 calc R U P A -1
H20C H 0.2492 0.3733 0.2418 0.090 Uiso 0.5 1 calc R U P A -1
C21 C -0.05291(13) 0.2500 0.3313(3) 0.0781(10) Uani 1 2 d S T P . .
H21A H -0.0589 0.1795 0.2592 0.117 Uiso 0.5 1 calc R U P B -1
H21B H -0.0678 0.3807 0.3208 0.117 Uiso 0.5 1 calc R U P B -1
H21C H -0.0782 0.1897 0.3929 0.117 Uiso 0.5 1 calc R U P B -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C2 1.736(2) . ?
S1 C5 1.728(3) . ?
O1 C7 1.244(3) . ?
N3 C2 1.362(3) . ?
N3 C4 1.399(3) . ?
N3 C14 1.451(3) . ?
N6 C2 1.321(3) . ?
N6 C7 1.361(3) . ?
C4 C5 1.335(3) . ?
C4 C20 1.500(3) . ?
C5 H5 0.9300 . ?
C7 C8 1.498(4) . ?
C8 C9 1.383(3) . ?
C8 C13 1.380(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.367(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.359(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.377(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.373(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.374(2) . ?
C14 C15 1.374(2) 8_565 ?
C15 H15 0.9300 . ?
C15 C16 1.388(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.375(3) . ?
C17 C16 1.375(3) 8_565 ?
C17 C21 1.512(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 S1 C2 90.41(12) . . ?
C2 N3 C4 115.28(19) . . ?
C2 N3 C14 120.13(18) . . ?
C4 N3 C14 124.6(2) . . ?
C2 N6 C7 116.9(2) . . ?
N3 C2 S1 109.73(17) . . ?
N6 C2 S1 129.70(19) . . ?
N6 C2 N3 120.6(2) . . ?
N3 C4 C20 119.0(2) . . ?
C5 C4 N3 110.9(2) . . ?
C5 C4 C20 130.1(2) . . ?
S1 C5 H5 123.2 . . ?
C4 C5 S1 113.64(19) . . ?
C4 C5 H5 123.2 . . ?
O1 C7 N6 125.1(2) . . ?
O1 C7 C8 120.6(2) . . ?
N6 C7 C8 114.3(2) . . ?
C9 C8 C7 119.8(2) . . ?
C13 C8 C7 121.3(2) . . ?
C13 C8 C9 118.9(2) . . ?
C8 C9 H9 119.4 . . ?
C10 C9 C8 121.2(3) . . ?
C10 C9 H9 119.4 . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.6(3) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.9 . . ?
C10 C11 C12 120.2(3) . . ?
C12 C11 H11 119.9 . . ?
C11 C12 H12 119.7 . . ?
C13 C12 C11 120.5(3) . . ?
C13 C12 H12 119.7 . . ?
C8 C13 H13 120.2 . . ?
C12 C13 C8 119.6(3) . . ?
C12 C13 H13 120.2 . . ?
C15 C14 N3 119.50(12) . . ?
C15 C14 N3 119.50(12) 8_565 . ?
C15 C14 C15 121.0(2) 8_565 . ?
C14 C15 H15 120.7 . . ?
C14 C15 C16 118.68(19) . . ?
C16 C15 H15 120.7 . . ?
C15 C16 H16 119.0 . . ?
C17 C16 C15 121.9(2) . . ?
C17 C16 H16 119.0 . . ?
C16 C17 C16 117.7(2) 8_565 . ?
C16 C17 C21 121.14(12) 8_565 . ?
C16 C17 C21 121.14(12) . . ?
C4 C20 H20A 109.5 . . ?
C4 C20 H20B 109.5 . . ?
C4 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C17 C21 H21A 109.5 . . ?
C17 C21 H21B 109.5 . . ?
C17 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 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
O1 C7 C8 C9 0.000(1) . . . . ?
O1 C7 C8 C13 180.000(1) . . . . ?
N3 C4 C5 S1 0.000(0) . . . . ?
N3 C14 C15 C16 176.68(18) . . . . ?
N6 C7 C8 C9 180.000(1) . . . . ?
N6 C7 C8 C13 0.000(1) . . . . ?
C2 S1 C5 C4 0.000(0) . . . . ?
C2 N3 C4 C5 0.000(0) . . . . ?
C2 N3 C4 C20 180.000(0) . . . . ?
C2 N3 C14 C15 -89.60(19) . . . . ?
C2 N3 C14 C15 89.60(19) . . . 8_565 ?
C2 N6 C7 O1 0.000(1) . . . . ?
C2 N6 C7 C8 180.000(0) . . . . ?
C4 N3 C2 S1 0.000(0) . . . . ?
C4 N3 C2 N6 180.000(0) . . . . ?
C4 N3 C14 C15 90.40(19) . . . . ?
C4 N3 C14 C15 -90.40(19) . . . 8_565 ?
C5 S1 C2 N3 0.000(0) . . . . ?
C5 S1 C2 N6 180.000(0) . . . . ?
C7 N6 C2 S1 0.000(0) . . . . ?
C7 N6 C2 N3 180.000(0) . . . . ?
C7 C8 C9 C10 180.000(1) . . . . ?
C7 C8 C13 C12 180.000(1) . . . . ?
C8 C9 C10 C11 0.000(1) . . . . ?
C9 C8 C13 C12 0.000(1) . . . . ?
C9 C10 C11 C12 0.000(1) . . . . ?
C10 C11 C12 C13 0.000(1) . . . . ?
C11 C12 C13 C8 0.000(1) . . . . ?
C13 C8 C9 C10 0.000(1) . . . . ?
C14 N3 C2 S1 180.000(0) . . . . ?
C14 N3 C2 N6 0.000(0) . . . . ?
C14 N3 C4 C5 180.000(0) . . . . ?
C14 N3 C4 C20 0.000(0) . . . . ?
C14 C15 C16 C17 0.2(3) . . . . ?
C15 C14 C15 C16 -2.5(4) 8_565 . . . ?
C15 C16 C17 C16 2.1(4) . . . 8_565 ?
C15 C16 C17 C21 -178.5(2) . . . . ?
C20 C4 C5 S1 180.000(0) . . . . ?

_olex2_submission_original_sample_id 'sph 61'
_olex2_submission_special_instructions 'No special instructions were received'
