# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_t
_database_code_depnum_ccdc_archive 'CCDC 2158056'
loop_
_audit_author_name
_audit_author_address
'Xiang-Gao Meng'
;Central China Normal University
China
;
_audit_update_record             
;
2022-03-12 deposited with the CCDC.	2022-07-03 downloaded from the CCDC.
;
_audit_creation_date             2021-04-21
_audit_creation_method           
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H15 N3 O'
_chemical_formula_sum            'C20 H15 N3 O'
_chemical_formula_weight         313.35
_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'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.726(3)
_cell_length_b                   16.029(4)
_cell_length_c                   10.295(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.005(4)
_cell_angle_gamma                90
_cell_volume                     1575.5(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3229
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.63
_cell_measurement_theta_min      2.38
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.992
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6379
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_unetI/netI     0.0488
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            11974
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.365
_diffrn_reflns_theta_min         2.382
_diffrn_ambient_temperature      296(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2268
_reflns_number_total             3198
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.246
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3198
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0485
_refine_ls_restrained_S_all      1.036
_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)+(0.0824P)²+0.1327P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1318
_refine_ls_wR_factor_ref         0.1492
_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: 
 C10(H10), C12(H12), C2(H2), C5(H5), C6(H6), C19(H19), C15(H15), C3(H3), 
 C4(H4), C17(H17), C18(H18), C16(H16) 
2.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
N1 N 0.95530(16) 0.09670(10) 0.84079(15) 0.0431(4) Uani 1 1 d . . . . .
N2 N 0.97072(15) 0.14040(10) 0.95765(14) 0.0406(4) Uani 1 1 d . . . . .
C9 C 1.09517(19) 0.12023(11) 1.03842(17) 0.0381(4) Uani 1 1 d . . . . .
N3 N 1.14356(16) 0.15055(10) 1.15943(15) 0.0450(4) Uani 1 1 d . . . . .
C8 C 1.16116(19) 0.06149(11) 0.97011(17) 0.0387(4) Uani 1 1 d . . . . .
O1 O 1.51911(17) -0.04086(10) 1.20880(17) 0.0675(5) Uani 1 1 d . . . . .
C13 C 1.4821(2) 0.02984(13) 1.22997(19) 0.0441(5) Uani 1 1 d . . . . .
C11 C 1.34629(19) 0.06266(12) 1.15648(18) 0.0418(5) Uani 1 1 d . . . . .
C10 C 1.2691(2) 0.12113(12) 1.21441(19) 0.0455(5) Uani 1 1 d . . . . .
H10 H 1.3090 0.1409 1.2980 0.055 Uiso 1 1 calc R . . . .
C7 C 1.0671(2) 0.04953(12) 0.84681(18) 0.0417(4) Uani 1 1 d . . . . .
C12 C 1.29044(19) 0.03124(12) 1.03204(19) 0.0418(4) Uani 1 1 d . . . . .
H12 H 1.3380 -0.0086 0.9918 0.050 Uiso 1 1 calc R . . . .
C1 C 0.86377(18) 0.19600(11) 0.97985(17) 0.0387(4) Uani 1 1 d . . . . .
C2 C 0.7283(2) 0.18445(12) 0.91013(19) 0.0449(5) Uani 1 1 d . . . . .
H2 H 0.7081 0.1410 0.8496 0.054 Uiso 1 1 calc R . . . .
C5 C 0.7880(2) 0.31391(12) 1.0891(2) 0.0503(5) Uani 1 1 d . . . . .
H5 H 0.8077 0.3576 1.1493 0.060 Uiso 1 1 calc R . . . .
C14 C 1.57286(19) 0.08328(12) 1.32844(19) 0.0433(5) Uani 1 1 d . . . . .
C6 C 0.8938(2) 0.26145(12) 1.0694(2) 0.0448(5) Uani 1 1 d . . . . .
H6 H 0.9847 0.2696 1.1155 0.054 Uiso 1 1 calc R . . . .
C19 C 1.6403(2) 0.04885(15) 1.4476(2) 0.0538(6) Uani 1 1 d . . . . .
H19 H 1.6246 -0.0066 1.4669 0.065 Uiso 1 1 calc R . . . .
C15 C 1.6001(2) 0.16511(14) 1.2988(2) 0.0554(5) Uani 1 1 d . . . . .
H15 H 1.5547 0.1891 1.2200 0.066 Uiso 1 1 calc R . . . .
C20 C 1.0848(2) -0.00653(14) 0.7360(2) 0.0548(6) Uani 1 1 d . . . . .
H20A H 1.0009 -0.0059 0.6695 0.082 Uiso 1 1 calc GR . . . .
H20B H 1.1028 -0.0623 0.7687 0.082 Uiso 1 1 calc GR . . . .
H20C H 1.1622 0.0125 0.6982 0.082 Uiso 1 1 calc GR . . . .
C3 C 0.6239(2) 0.23796(13) 0.9315(2) 0.0514(5) Uani 1 1 d . . . . .
H3 H 0.5329 0.2303 0.8851 0.062 Uiso 1 1 calc R . . . .
C4 C 0.6528(2) 0.30269(13) 1.0208(2) 0.0525(5) Uani 1 1 d . . . . .
H4 H 0.5817 0.3385 1.0348 0.063 Uiso 1 1 calc R . . . .
C17 C 1.7587(2) 0.1756(2) 1.5072(3) 0.0810(9) Uani 1 1 d . . . . .
H17 H 1.8212 0.2070 1.5677 0.097 Uiso 1 1 calc R . . . .
C18 C 1.7295(2) 0.0961(2) 1.5362(2) 0.0707(7) Uani 1 1 d . . . . .
H18 H 1.7707 0.0734 1.6175 0.085 Uiso 1 1 calc R . . . .
C16 C 1.6955(3) 0.21060(17) 1.3876(3) 0.0742(7) Uani 1 1 d . . . . .
H16 H 1.7175 0.2649 1.3670 0.089 Uiso 1 1 calc R . . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N2 1.375(2) . ?
N1 C7 1.316(2) . ?
N2 C9 1.370(2) . ?
N2 C1 1.421(2) . ?
C9 N3 1.336(2) . ?
C9 C8 1.402(3) . ?
N3 C10 1.330(2) . ?
C8 C7 1.429(3) . ?
C8 C12 1.384(3) . ?
O1 C13 1.221(2) . ?
C13 C11 1.487(3) . ?
C13 C14 1.483(3) . ?
C11 C10 1.403(3) . ?
C11 C12 1.387(3) . ?
C10 H10 0.9300 . ?
C7 C20 1.488(3) . ?
C12 H12 0.9300 . ?
C1 C2 1.387(3) . ?
C1 C6 1.390(3) . ?
C2 H2 0.9300 . ?
C2 C3 1.378(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.374(3) . ?
C5 C4 1.379(3) . ?
C14 C19 1.390(3) . ?
C14 C15 1.384(3) . ?
C6 H6 0.9300 . ?
C19 H19 0.9300 . ?
C19 C18 1.362(3) . ?
C15 H15 0.9300 . ?
C15 C16 1.380(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C3 H3 0.9300 . ?
C3 C4 1.379(3) . ?
C4 H4 0.9300 . ?
C17 H17 0.9300 . ?
C17 C18 1.352(4) . ?
C17 C16 1.386(4) . ?
C18 H18 0.9300 . ?
C16 H16 0.9300 . ?

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 N1 N2 107.47(14) . . ?
N1 N2 C1 119.95(14) . . ?
C9 N2 N1 110.30(14) . . ?
C9 N2 C1 129.74(15) . . ?
N2 C9 C8 106.86(15) . . ?
N3 C9 N2 126.38(17) . . ?
N3 C9 C8 126.76(16) . . ?
C10 N3 C9 113.51(16) . . ?
C9 C8 C7 105.00(16) . . ?
C12 C8 C9 117.82(17) . . ?
C12 C8 C7 137.17(18) . . ?
O1 C13 C11 120.06(18) . . ?
O1 C13 C14 120.04(17) . . ?
C14 C13 C11 119.90(17) . . ?
C10 C11 C13 121.01(17) . . ?
C12 C11 C13 119.64(17) . . ?
C12 C11 C10 119.23(17) . . ?
N3 C10 C11 125.31(17) . . ?
N3 C10 H10 117.3 . . ?
C11 C10 H10 117.3 . . ?
N1 C7 C8 110.36(16) . . ?
N1 C7 C20 121.77(17) . . ?
C8 C7 C20 127.87(18) . . ?
C8 C12 C11 117.34(18) . . ?
C8 C12 H12 121.3 . . ?
C11 C12 H12 121.3 . . ?
C2 C1 N2 119.03(16) . . ?
C2 C1 C6 120.15(17) . . ?
C6 C1 N2 120.83(16) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 C1 119.35(18) . . ?
C3 C2 H2 120.3 . . ?
C6 C5 H5 119.6 . . ?
C6 C5 C4 120.85(19) . . ?
C4 C5 H5 119.6 . . ?
C19 C14 C13 119.5(2) . . ?
C15 C14 C13 120.71(18) . . ?
C15 C14 C19 119.5(2) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 C1 119.44(18) . . ?
C5 C6 H6 120.3 . . ?
C14 C19 H19 119.9 . . ?
C18 C19 C14 120.2(2) . . ?
C18 C19 H19 119.9 . . ?
C14 C15 H15 120.4 . . ?
C16 C15 C14 119.2(2) . . ?
C16 C15 H15 120.4 . . ?
C7 C20 H20A 109.5 . . ?
C7 C20 H20B 109.5 . . ?
C7 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.81(19) . . ?
C4 C3 H3 119.6 . . ?
C5 C4 H4 120.3 . . ?
C3 C4 C5 119.40(19) . . ?
C3 C4 H4 120.3 . . ?
C18 C17 H17 120.0 . . ?
C18 C17 C16 120.1(2) . . ?
C16 C17 H17 120.0 . . ?
C19 C18 H18 119.7 . . ?
C17 C18 C19 120.7(3) . . ?
C17 C18 H18 119.7 . . ?
C15 C16 C17 120.2(3) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 N2 C9 N3 -179.63(18) . . . . ?
N1 N2 C9 C8 0.0(2) . . . . ?
N1 N2 C1 C2 23.1(3) . . . . ?
N1 N2 C1 C6 -156.53(18) . . . . ?
N2 N1 C7 C8 -0.3(2) . . . . ?
N2 N1 C7 C20 179.89(18) . . . . ?
N2 C9 N3 C10 -178.76(17) . . . . ?
N2 C9 C8 C7 -0.1(2) . . . . ?
N2 C9 C8 C12 179.89(16) . . . . ?
N2 C1 C2 C3 179.79(18) . . . . ?
N2 C1 C6 C5 -179.71(18) . . . . ?
C9 N2 C1 C2 -156.00(19) . . . . ?
C9 N2 C1 C6 24.4(3) . . . . ?
C9 N3 C10 C11 -1.3(3) . . . . ?
C9 C8 C7 N1 0.2(2) . . . . ?
C9 C8 C7 C20 -179.91(19) . . . . ?
C9 C8 C12 C11 -1.2(3) . . . . ?
N3 C9 C8 C7 179.49(19) . . . . ?
N3 C9 C8 C12 -0.5(3) . . . . ?
C8 C9 N3 C10 1.7(3) . . . . ?
O1 C13 C11 C10 149.3(2) . . . . ?
O1 C13 C11 C12 -26.6(3) . . . . ?
O1 C13 C14 C19 -41.6(3) . . . . ?
O1 C13 C14 C15 133.1(2) . . . . ?
C13 C11 C10 N3 -176.15(19) . . . . ?
C13 C11 C12 C8 177.47(17) . . . . ?
C13 C14 C19 C18 176.74(18) . . . . ?
C13 C14 C15 C16 -173.83(19) . . . . ?
C11 C13 C14 C19 138.78(19) . . . . ?
C11 C13 C14 C15 -46.5(3) . . . . ?
C10 C11 C12 C8 1.5(3) . . . . ?
C7 N1 N2 C9 0.2(2) . . . . ?
C7 N1 N2 C1 -179.10(16) . . . . ?
C7 C8 C12 C11 178.9(2) . . . . ?
C12 C8 C7 N1 -179.8(2) . . . . ?
C12 C8 C7 C20 0.1(4) . . . . ?
C12 C11 C10 N3 -0.3(3) . . . . ?
C1 N2 C9 N3 -0.5(3) . . . . ?
C1 N2 C9 C8 179.16(17) . . . . ?
C1 C2 C3 C4 0.2(3) . . . . ?
C2 C1 C6 C5 0.7(3) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C14 C13 C11 C10 -31.1(3) . . . . ?
C14 C13 C11 C12 153.04(18) . . . . ?
C14 C19 C18 C17 -3.1(3) . . . . ?
C14 C15 C16 C17 -2.6(3) . . . . ?
C6 C1 C2 C3 -0.6(3) . . . . ?
C6 C5 C4 C3 -0.1(3) . . . . ?
C19 C14 C15 C16 0.9(3) . . . . ?
C15 C14 C19 C18 2.0(3) . . . . ?
C4 C5 C6 C1 -0.3(3) . . . . ?
C18 C17 C16 C15 1.5(4) . . . . ?
C16 C17 C18 C19 1.4(4) . . . . ?

_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_y
_database_code_depnum_ccdc_archive 'CCDC 2165134'
loop_
_audit_author_name
_audit_author_address
'Xiang-Gao Meng'
;Central China Normal University
China
;
_audit_update_record             
;
2022-04-07 deposited with the CCDC.	2022-07-03 downloaded from the CCDC.
;
_audit_creation_date             2022-04-07
_audit_creation_method           
; 
Olex2 1.2 
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) 
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H15 N3 O3 S'
_chemical_formula_sum            'C17 H15 N3 O3 S'
_chemical_formula_weight         341.38
_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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   11.285(2)
_cell_length_b                   10.0877(19)
_cell_length_c                   14.445(3)
_cell_angle_alpha                90
_cell_angle_beta                 105.695(3)
_cell_angle_gamma                90
_cell_volume                     1583.1(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5781
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      29.23
_cell_measurement_theta_min      2.49
_shelx_estimated_absorpt_T_max   0.973
_shelx_estimated_absorpt_T_min   0.948
_exptl_absorpt_coefficient_mu    0.226
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.6818
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2008/1 (Bruker,2008)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14713
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.327
_diffrn_reflns_theta_min         2.043
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3103
_reflns_number_total             4312
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XM (Sheldrick, 2008)'
_refine_diff_density_max         0.274
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         4312
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0479
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0794P)²+0.3548P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1369
_refine_ls_wR_factor_ref         0.1565
_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: 
 C3(H3), C4(H4), C6(H6), C7(H7), C10(H10), C11(H11) 
2.b Idealised Me refined as rotating group: 
 C1(H1A,H1B,H1C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C) 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.32823(5) 0.41777(6) 0.34400(4) 0.0695(2) Uani 1 1 d . . . . .
O1 O 0.49784(13) 0.01327(13) 0.72249(10) 0.0641(4) Uani 1 1 d . . . . .
O2 O 0.70193(15) 0.56311(14) 0.89740(9) 0.0693(4) Uani 1 1 d . . . . .
O3 O 0.70010(13) 0.49508(16) 1.20728(9) 0.0654(4) Uani 1 1 d . . . . .
N1 N 0.69697(12) 0.53200(14) 1.05176(9) 0.0467(3) Uani 1 1 d . . . . .
N2 N 0.60503(13) 0.34158(15) 1.09836(9) 0.0485(3) Uani 1 1 d . . . . .
N3 N 0.51959(14) 0.17688(15) 0.98881(10) 0.0541(4) Uani 1 1 d . . . . .
C1 C 0.2650(2) 0.5749(2) 0.36333(19) 0.0815(7) Uani 1 1 d . . . . .
H1A H 0.2364 0.6205 0.3031 0.122 Uiso 1 1 calc GR . . . .
H1B H 0.3273 0.6270 0.4064 0.122 Uiso 1 1 calc GR . . . .
H1C H 0.1975 0.5613 0.3909 0.122 Uiso 1 1 calc GR . . . .
C2 C 0.37244(15) 0.34635(19) 0.45890(12) 0.0514(4) Uani 1 1 d . . . . .
C3 C 0.35325(17) 0.40130(19) 0.54194(13) 0.0545(4) Uani 1 1 d . . . . .
H3 H 0.3145 0.4831 0.5391 0.065 Uiso 1 1 calc R . . . .
C4 C 0.39161(15) 0.33469(18) 0.62905(12) 0.0509(4) Uani 1 1 d . . . . .
H4 H 0.3784 0.3728 0.6840 0.061 Uiso 1 1 calc R . . . .
C5 C 0.44913(14) 0.21266(17) 0.63547(11) 0.0456(4) Uani 1 1 d . . . . .
C6 C 0.46758(17) 0.15807(19) 0.55167(13) 0.0565(4) Uani 1 1 d . . . . .
H6 H 0.5062 0.0761 0.5544 0.068 Uiso 1 1 calc R . . . .
C7 C 0.42982(17) 0.2231(2) 0.46537(13) 0.0590(5) Uani 1 1 d . . . . .
H7 H 0.4427 0.1845 0.4104 0.071 Uiso 1 1 calc R . . . .
C8 C 0.48714(15) 0.13315(18) 0.72509(12) 0.0478(4) Uani 1 1 d . . . . .
C9 C 0.51480(15) 0.19966(17) 0.82082(11) 0.0464(4) Uani 1 1 d . . . . .
C10 C 0.49243(17) 0.13124(18) 0.89858(13) 0.0533(4) Uani 1 1 d . . . . .
H10 H 0.4561 0.0480 0.8867 0.064 Uiso 1 1 calc R . . . .
C11 C 0.57181(14) 0.32150(16) 0.83969(11) 0.0439(3) Uani 1 1 d . . . . .
H11 H 0.5878 0.3710 0.7901 0.053 Uiso 1 1 calc R . . . .
C12 C 0.57532(14) 0.29415(16) 1.00459(11) 0.0426(3) Uani 1 1 d . . . . .
C13 C 0.60527(13) 0.36992(16) 0.93343(10) 0.0408(3) Uani 1 1 d . . . . .
C14 C 0.67104(14) 0.49448(17) 0.95625(11) 0.0458(4) Uani 1 1 d . . . . .
C15 C 0.66909(15) 0.45761(18) 1.12472(11) 0.0478(4) Uani 1 1 d . . . . .
C16 C 0.76442(19) 0.6559(2) 1.08080(14) 0.0624(5) Uani 1 1 d . . . . .
H16A H 0.8484 0.6362 1.1139 0.094 Uiso 1 1 calc GR . . . .
H16B H 0.7271 0.7044 1.1227 0.094 Uiso 1 1 calc GR . . . .
H16C H 0.7619 0.7082 1.0248 0.094 Uiso 1 1 calc GR . . . .
C17 C 0.5738(2) 0.2638(2) 1.17420(13) 0.0686(5) Uani 1 1 d . . . . .
H17A H 0.4915 0.2301 1.1510 0.103 Uiso 1 1 calc GR . . . .
H17B H 0.5792 0.3192 1.2292 0.103 Uiso 1 1 calc GR . . . .
H17C H 0.6303 0.1911 1.1921 0.103 Uiso 1 1 calc GR . . . .


_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 C1 1.791(3) . ?
S1 C2 1.7534(19) . ?
O1 C8 1.217(2) . ?
O2 C14 1.218(2) . ?
O3 C15 1.209(2) . ?
N1 C14 1.3834(19) . ?
N1 C15 1.397(2) . ?
N1 C16 1.464(2) . ?
N2 C12 1.389(2) . ?
N2 C15 1.374(2) . ?
N2 C17 1.466(2) . ?
N3 C10 1.337(2) . ?
N3 C12 1.330(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.391(2) . ?
C2 C7 1.393(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.388(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.383(2) . ?
C5 C6 1.396(2) . ?
C5 C8 1.484(2) . ?
C6 H6 0.9300 . ?
C6 C7 1.371(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.492(2) . ?
C9 C10 1.398(2) . ?
C9 C11 1.380(2) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C11 C13 1.392(2) . ?
C12 C13 1.394(2) . ?
C13 C14 1.451(2) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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 C1 103.85(11) . . ?
C14 N1 C15 125.12(15) . . ?
C14 N1 C16 118.20(15) . . ?
C15 N1 C16 116.61(14) . . ?
C12 N2 C17 120.05(16) . . ?
C15 N2 C12 122.25(14) . . ?
C15 N2 C17 117.62(14) . . ?
C12 N3 C10 116.50(15) . . ?
S1 C1 H1A 109.5 . . ?
S1 C1 H1B 109.5 . . ?
S1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 S1 125.58(16) . . ?
C3 C2 C7 118.41(17) . . ?
C7 C2 S1 115.99(13) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.38(17) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.4 . . ?
C5 C4 C3 121.14(15) . . ?
C5 C4 H4 119.4 . . ?
C4 C5 C6 118.07(16) . . ?
C4 C5 C8 123.99(14) . . ?
C6 C5 C8 117.87(16) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 C5 121.14(17) . . ?
C7 C6 H6 119.4 . . ?
C2 C7 H7 119.6 . . ?
C6 C7 C2 120.85(16) . . ?
C6 C7 H7 119.6 . . ?
O1 C8 C5 121.19(15) . . ?
O1 C8 C9 118.54(16) . . ?
C5 C8 C9 120.27(15) . . ?
C10 C9 C8 118.98(15) . . ?
C11 C9 C8 123.58(15) . . ?
C11 C9 C10 117.18(15) . . ?
N3 C10 C9 124.71(16) . . ?
N3 C10 H10 117.6 . . ?
C9 C10 H10 117.6 . . ?
C9 C11 H11 120.2 . . ?
C9 C11 C13 119.61(15) . . ?
C13 C11 H11 120.2 . . ?
N2 C12 C13 119.17(15) . . ?
N3 C12 N2 116.84(14) . . ?
N3 C12 C13 123.99(14) . . ?
C11 C13 C12 117.95(15) . . ?
C11 C13 C14 120.81(14) . . ?
C12 C13 C14 121.23(14) . . ?
O2 C14 N1 121.14(16) . . ?
O2 C14 C13 123.99(15) . . ?
N1 C14 C13 114.87(14) . . ?
O3 C15 N1 120.80(17) . . ?
O3 C15 N2 121.99(17) . . ?
N2 C15 N1 117.21(13) . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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 C2 C3 C4 179.47(13) . . . . ?
S1 C2 C7 C6 -179.67(14) . . . . ?
O1 C8 C9 C10 -31.3(2) . . . . ?
O1 C8 C9 C11 142.69(17) . . . . ?
N2 C12 C13 C11 -178.49(13) . . . . ?
N2 C12 C13 C14 2.5(2) . . . . ?
N3 C12 C13 C11 1.8(2) . . . . ?
N3 C12 C13 C14 -177.23(15) . . . . ?
C1 S1 C2 C3 3.38(18) . . . . ?
C1 S1 C2 C7 -177.66(15) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C2 C7 C6 -0.6(3) . . . . ?
C3 C4 C5 C6 0.0(2) . . . . ?
C3 C4 C5 C8 -176.99(16) . . . . ?
C4 C5 C6 C7 -0.1(3) . . . . ?
C4 C5 C8 O1 154.77(17) . . . . ?
C4 C5 C8 C9 -26.1(2) . . . . ?
C5 C6 C7 C2 0.4(3) . . . . ?
C5 C8 C9 C10 149.47(16) . . . . ?
C5 C8 C9 C11 -36.5(2) . . . . ?
C6 C5 C8 O1 -22.2(2) . . . . ?
C6 C5 C8 C9 156.97(15) . . . . ?
C7 C2 C3 C4 0.5(3) . . . . ?
C8 C5 C6 C7 177.08(16) . . . . ?
C8 C9 C10 N3 176.11(16) . . . . ?
C8 C9 C11 C13 -173.48(14) . . . . ?
C9 C11 C13 C12 -2.3(2) . . . . ?
C9 C11 C13 C14 176.78(14) . . . . ?
C10 N3 C12 N2 -179.33(15) . . . . ?
C10 N3 C12 C13 0.4(2) . . . . ?
C10 C9 C11 C13 0.7(2) . . . . ?
C11 C9 C10 N3 1.7(3) . . . . ?
C11 C13 C14 O2 -0.7(3) . . . . ?
C11 C13 C14 N1 179.07(13) . . . . ?
C12 N2 C15 O3 -176.21(15) . . . . ?
C12 N2 C15 N1 4.1(2) . . . . ?
C12 N3 C10 C9 -2.2(3) . . . . ?
C12 C13 C14 O2 178.29(16) . . . . ?
C12 C13 C14 N1 -1.9(2) . . . . ?
C14 N1 C15 O3 176.60(15) . . . . ?
C14 N1 C15 N2 -3.7(2) . . . . ?
C15 N1 C14 O2 -177.61(16) . . . . ?
C15 N1 C14 C13 2.6(2) . . . . ?
C15 N2 C12 N3 176.10(14) . . . . ?
C15 N2 C12 C13 -3.6(2) . . . . ?
C16 N1 C14 O2 -0.9(2) . . . . ?
C16 N1 C14 C13 179.31(14) . . . . ?
C16 N1 C15 O3 -0.2(2) . . . . ?
C16 N1 C15 N2 179.55(14) . . . . ?
C17 N2 C12 N3 -0.6(2) . . . . ?
C17 N2 C12 C13 179.70(15) . . . . ?
C17 N2 C15 O3 0.5(2) . . . . ?
C17 N2 C15 N1 -179.16(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
