# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_b
_database_code_depnum_ccdc_archive 'CCDC 2097642'
loop_
_audit_author_name
_audit_author_address
'Zhao Chenyang'
;Tianjin University
China
;
_audit_update_record             
;
2021-07-20 deposited with the CCDC.	2021-08-19 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-97
_audit_creation_date             2021-06-04
_chemical_formula_sum            'C21 H25 N5 O2 S'
_chemical_formula_weight         411.520
_refine_ls_R_factor_all          0.132
_cell_length_a                   9.2609(19)
_cell_length_b                   24.972(5)
_cell_length_c                   9.6398(19)
_cell_angle_alpha                90.000
_cell_angle_beta                 109.03(3)
_cell_angle_gamma                90.000
_cell_volume                     2107.5(7)
_cell_formula_units_Z            4
_symmetry_int_tables_number      14
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  -P_2yn

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+z

loop_
_atom_type_symbol
_atom_type_oxidation_number
_atom_type_radius_bond
S ? 1.200
O ? 1.200
C ? 1.200
H ? 1.200
N ? 1.200


loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_attached_hydrogens
_atom_site_calc_flag
_atom_site_thermal_displace_type
_atom_site_u_iso_or_equiv
S1 S 0.5366(1) 0.1891(0) 0.9604(1) 1.000 4 e ? d Uani 0.0484(3)
O1 O 0.4998(3) 0.2326(1) 0.8565(3) 1.000 4 e ? d Uani 0.0668(7)
O2 O 0.6843(3) 0.1637(1) 0.9923(3) 1.000 4 e ? d Uani 0.0640(7)
C1 C 0.4337(4) 0.0857(1) 0.9251(3) 1.000 4 e ? d Uani 0.0460(7)
H1B H 0.5335 0.0756 0.9769 1.000 4 e ? calc Uiso 0.05500
C2 C 0.3226(4) 0.0474(1) 0.8767(3) 1.000 4 e ? d Uani 0.0494(8)
H2B H 0.3482 0.0114 0.8950 1.000 4 e ? calc Uiso 0.05900
C3 C 0.1712(4) 0.0614(1) 0.8000(3) 1.000 4 e ? d Uani 0.0490(8)
C4 C 0.1362(4) 0.1154(1) 0.7741(3) 1.000 4 e ? d Uani 0.0508(8)
H4A H 0.0361 0.1255 0.7237 1.000 4 e ? calc Uiso 0.06100
C5 C 0.2472(4) 0.1542(1) 0.8217(3) 1.000 4 e ? d Uani 0.0479(8)
H5A H 0.2217 0.1902 0.8037 1.000 4 e ? calc Uiso 0.05800
C6 C 0.3975(3) 0.1395(1) 0.8968(3) 1.000 4 e ? d Uani 0.0432(7)
C7 C 0.5181(4) 0.2113(1) 1.1253(3) 1.000 4 e ? d Uani 0.0438(7)
C8 C 0.4135(4) 0.2514(1) 1.1249(4) 1.000 4 e ? d Uani 0.0573(9)
H8A H 0.3611 0.2688 1.0378 1.000 4 e ? calc Uiso 0.06900
C9 C 0.3875(4) 0.2652(1) 1.2521(4) 1.000 4 e ? d Uani 0.0635(10)
H9A H 0.3189 0.2925 1.2510 1.000 4 e ? calc Uiso 0.07600
C10 C 0.4633(4) 0.2387(1) 1.3844(4) 1.000 4 e ? d Uani 0.0526(8)
C11 C 0.5690(4) 0.1995(1) 1.3830(4) 1.000 4 e ? d Uani 0.0503(8)
H11A H 0.6227 0.1821 1.4698 1.000 4 e ? calc Uiso 0.06000
C12 C 0.5954(4) 0.1860(1) 1.2563(4) 1.000 4 e ? d Uani 0.0475(8)
H12A H 0.6664 0.1595 1.2580 1.000 4 e ? calc Uiso 0.05700
C13 C 0.0275(5) 0.1255(2) 0.3393(5) 1.000 4 e ? d Uani 0.0831(13)
H13A H -0.0448 0.1263 0.3928 1.000 4 e ? calc Uiso 0.10000
H13B H 0.0511 0.1622 0.3213 1.000 4 e ? calc Uiso 0.10000
C14 C 0.1694(5) 0.0980(2) 0.4289(4) 1.000 4 e ? d Uani 0.0723(11)
H14A H 0.2167 0.1185 0.5175 1.000 4 e ? calc Uiso 0.08700
H14B H 0.1432 0.0630 0.4577 1.000 4 e ? calc Uiso 0.08700
C15 C 0.2118(5) 0.0725(2) 0.1988(4) 1.000 4 e ? d Uani 0.0686(10)
H15A H 0.1915 0.0344 0.1994 1.000 4 e ? calc Uiso 0.08200
H15B H 0.2847 0.0778 0.1471 1.000 4 e ? calc Uiso 0.08200
C16 C 0.0660(5) 0.1012(2) 0.1181(5) 1.000 4 e ? d Uani 0.0791(12)
H16A H 0.0879 0.1384 0.1041 1.000 4 e ? calc Uiso 0.09500
H16B H 0.0203 0.0851 0.0221 1.000 4 e ? calc Uiso 0.09500
C17 C 0.4273(4) 0.0793(1) 0.4266(4) 1.000 4 e ? d Uani 0.0498(8)
C18 C 0.4941(5) 0.0909(1) 0.5774(4) 1.000 4 e ? d Uani 0.0595(9)
H18A H 0.4347 0.1055 0.6293 1.000 4 e ? calc Uiso 0.07100
C19 C 0.6451(5) 0.0809(1) 0.6477(4) 1.000 4 e ? d Uani 0.0688(11)
H19A H 0.6841 0.0893 0.7470 1.000 4 e ? calc Uiso 0.08300
C20 C 0.6770(5) 0.0476(2) 0.4435(5) 1.000 4 e ? d Uani 0.0684(10)
H20A H 0.7395 0.0320 0.3964 1.000 4 e ? calc Uiso 0.08200
C21 C 0.5274(4) 0.0558(1) 0.3621(4) 1.000 4 e ? d Uani 0.0571(9)
H21A H 0.4920 0.0457 0.2638 1.000 4 e ? calc Uiso 0.06900
N1 N 0.0601(4) 0.0239(1) 0.7504(4) 1.000 4 e ? d Uani 0.0717(9)
H1C H 0.0820 -0.0095 0.7659 1.000 4 e ? calc Uiso 0.08600
H1D H -0.0321 0.0335 0.7036 1.000 4 e ? calc Uiso 0.08600
N2 N 0.4353(4) 0.2523(1) 1.5107(4) 1.000 4 e ? d Uani 0.0810(11)
H2C H 0.4838 0.2365 1.5917 1.000 4 e ? calc Uiso 0.09700
H2D H 0.3693 0.2767 1.5090 1.000 4 e ? calc Uiso 0.09700
N3 N -0.0407(4) 0.0982(1) 0.2000(4) 1.000 4 e ? d Uani 0.0684(9)
H3A H -0.1288 0.0830 0.1711 1.000 4 e ? calc Uiso 0.08200
N4 N 0.2789(4) 0.0913(1) 0.3502(3) 1.000 4 e ? d Uani 0.0567(8)
N5 N 0.7411(4) 0.0602(1) 0.5848(4) 1.000 4 e ? d Uani 0.0724(9)



loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O1 . . 1.442(2) no
S1 O2 . . 1.447(2) no
S1 C6 . . 1.747(3) no
S1 C7 . . 1.743(3) no
C1 C2 . . 1.371(4) no
C1 C6 . . 1.391(4) no
C1 H1B . . 0.9300 no
C2 C3 . . 1.400(5) no
C2 H2B . . 0.9300 no
C3 N1 . . 1.358(4) no
C3 C4 . . 1.389(4) no
C4 C5 . . 1.379(4) no
C4 H4A . . 0.9300 no
C5 C6 . . 1.393(4) no
C5 H5A . . 0.9300 no
C7 C12 . . 1.383(4) no
C7 C8 . . 1.393(4) no
C8 C9 . . 1.369(5) no
C8 H8A . . 0.9300 no
C9 C10 . . 1.405(5) no
C9 H9A . . 0.9300 no
C10 C11 . . 1.387(5) no
C10 N2 . . 1.367(4) no
C11 C12 . . 1.363(4) no
C11 H11A . . 0.9300 no
C12 H12A . . 0.9300 no
C13 N3 . . 1.454(5) no
C13 C14 . . 1.485(6) no
C13 H13A . . 0.9700 no
C13 H13B . . 0.9700 no
C14 N4 . . 1.461(5) no
C14 H14A . . 0.9700 no
C14 H14B . . 0.9700 no
C15 N4 . . 1.465(4) no
C15 C16 . . 1.503(6) no
C15 H15A . . 0.9700 no
C15 H15B . . 0.9700 no
C16 N3 . . 1.454(5) no
C16 H16A . . 0.9700 no
C16 H16B . . 0.9700 no
C17 N4 . . 1.364(5) no
C17 C21 . . 1.403(5) no
C17 C18 . . 1.412(5) no
C18 C19 . . 1.363(5) no
C18 H18A . . 0.9300 no
C19 N5 . . 1.334(5) no
C19 H19A . . 0.9300 no
C20 N5 . . 1.333(5) no
C20 C21 . . 1.366(5) no
C20 H20A . . 0.9300 no
C21 H21A . . 0.9300 no
N1 H1C . . 0.8600 no
N1 H1D . . 0.8600 no
N2 H2C . . 0.8600 no
N2 H2D . . 0.8600 no
N3 H3A . . 0.8600 no

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 S1 O2 . . . 118.11(15) no
O1 S1 C6 . . . 108.10(15) no
O2 S1 C6 . . . 107.51(15) no
O1 S1 C7 . . . 108.83(14) no
O2 S1 C7 . . . 108.22(15) no
C6 S1 C7 . . . 105.35(14) no
C2 C1 C6 . . . 120.1(3) no
C2 C1 H1B . . . 119.90 no
C6 C1 H1B . . . 119.90 no
C1 C2 C3 . . . 121.1(3) no
C1 C2 H2B . . . 119.50 no
C3 C2 H2B . . . 119.50 no
N1 C3 C2 . . . 121.7(3) no
N1 C3 C4 . . . 120.1(3) no
C2 C3 C4 . . . 118.2(3) no
C5 C4 C3 . . . 121.2(3) no
C5 C4 H4A . . . 119.40 no
C3 C4 H4A . . . 119.40 no
C4 C5 C6 . . . 119.8(3) no
C4 C5 H5A . . . 120.10 no
C6 C5 H5A . . . 120.10 no
C5 C6 C1 . . . 119.5(3) no
C5 C6 S1 . . . 119.5(2) no
C1 C6 S1 . . . 120.9(2) no
C12 C7 C8 . . . 118.8(3) no
C12 C7 S1 . . . 120.8(2) no
C8 C7 S1 . . . 120.1(2) no
C9 C8 C7 . . . 120.3(3) no
C9 C8 H8A . . . 119.80 no
C7 C8 H8A . . . 119.80 no
C8 C9 C10 . . . 120.8(3) no
C8 C9 H9A . . . 119.60 no
C10 C9 H9A . . . 119.60 no
C11 C10 N2 . . . 121.6(3) no
C11 C10 C9 . . . 117.9(3) no
N2 C10 C9 . . . 120.5(3) no
C12 C11 C10 . . . 121.0(3) no
C12 C11 H11A . . . 119.50 no
C10 C11 H11A . . . 119.50 no
C11 C12 C7 . . . 121.0(3) no
C11 C12 H12A . . . 119.50 no
C7 C12 H12A . . . 119.50 no
N3 C13 C14 . . . 110.8(3) no
N3 C13 H13A . . . 109.50 no
C14 C13 H13A . . . 109.50 no
N3 C13 H13B . . . 109.50 no
C14 C13 H13B . . . 109.50 no
H13A C13 H13B . . . 108.10 no
N4 C14 C13 . . . 112.5(3) no
N4 C14 H14A . . . 109.10 no
C13 C14 H14A . . . 109.10 no
N4 C14 H14B . . . 109.10 no
C13 C14 H14B . . . 109.10 no
H14A C14 H14B . . . 107.80 no
N4 C15 C16 . . . 112.4(3) no
N4 C15 H15A . . . 109.10 no
C16 C15 H15A . . . 109.10 no
N4 C15 H15B . . . 109.10 no
C16 C15 H15B . . . 109.10 no
H15A C15 H15B . . . 107.90 no
N3 C16 C15 . . . 110.5(3) no
N3 C16 H16A . . . 109.60 no
C15 C16 H16A . . . 109.60 no
N3 C16 H16B . . . 109.60 no
C15 C16 H16B . . . 109.60 no
H16A C16 H16B . . . 108.10 no
N4 C17 C21 . . . 123.2(3) no
N4 C17 C18 . . . 122.5(3) no
C21 C17 C18 . . . 114.3(4) no
C19 C18 C17 . . . 120.5(3) no
C19 C18 H18A . . . 119.70 no
C17 C18 H18A . . . 119.70 no
N5 C19 C18 . . . 125.0(4) no
N5 C19 H19A . . . 117.50 no
C18 C19 H19A . . . 117.50 no
N5 C20 C21 . . . 125.6(4) no
N5 C20 H20A . . . 117.20 no
C21 C20 H20A . . . 117.20 no
C20 C21 C17 . . . 120.0(4) no
C20 C21 H21A . . . 120.00 no
C17 C21 H21A . . . 120.00 no
C3 N1 H1C . . . 120.00 no
C3 N1 H1D . . . 120.00 no
H1C N1 H1D . . . 120.00 no
C10 N2 H2C . . . 120.00 no
C10 N2 H2D . . . 120.00 no
H2C N2 H2D . . . 120.00 no
C16 N3 C13 . . . 108.1(4) no
C16 N3 H3A . . . 126.00 no
C13 N3 H3A . . . 126.00 no
C17 N4 C15 . . . 119.6(3) no
C17 N4 C14 . . . 119.5(3) no
C15 N4 C14 . . . 114.4(3) no
C19 N5 C20 . . . 114.5(4) no

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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -0.8(5) no
C1 C2 C3 N1 . . . . 179.5(3) no
C1 C2 C3 C4 . . . . 0.0(5) no
N1 C3 C4 C5 . . . . -179.2(3) no
C2 C3 C4 C5 . . . . 0.3(5) no
C3 C4 C5 C6 . . . . 0.2(5) no
C4 C5 C6 C1 . . . . -1.0(5) no
C4 C5 C6 S1 . . . . -178.6(2) no
C2 C1 C6 C5 . . . . 1.3(4) no
C2 C1 C6 S1 . . . . 178.8(2) no
O1 S1 C6 C5 . . . . -34.4(3) no
O2 S1 C6 C5 . . . . -162.9(2) no
C7 S1 C6 C5 . . . . 81.9(3) no
O1 S1 C6 C1 . . . . 148.1(3) no
O2 S1 C6 C1 . . . . 19.6(3) no
C7 S1 C6 C1 . . . . -95.6(3) no
O1 S1 C7 C12 . . . . -156.7(3) no
O2 S1 C7 C12 . . . . -27.2(3) no
C6 S1 C7 C12 . . . . 87.6(3) no
O1 S1 C7 C8 . . . . 29.6(3) no
O2 S1 C7 C8 . . . . 159.1(3) no
C6 S1 C7 C8 . . . . -86.1(3) no
C12 C7 C8 C9 . . . . -0.3(5) no
S1 C7 C8 C9 . . . . 173.5(3) no
C7 C8 C9 C10 . . . . -1.2(6) no
C8 C9 C10 C11 . . . . 2.3(5) no
C8 C9 C10 N2 . . . . -179.2(3) no
N2 C10 C11 C12 . . . . 179.7(3) no
C9 C10 C11 C12 . . . . -1.8(5) no
C10 C11 C12 C7 . . . . 0.3(5) no
C8 C7 C12 C11 . . . . 0.8(5) no
S1 C7 C12 C11 . . . . -173.0(2) no
N3 C13 C14 N4 . . . . 54.4(5) no
N4 C15 C16 N3 . . . . -53.5(5) no
N4 C17 C18 C19 . . . . -176.3(3) no
C21 C17 C18 C19 . . . . 2.1(5) no
C17 C18 C19 N5 . . . . 0.0(6) no
N5 C20 C21 C17 . . . . 0.2(6) no
N4 C17 C21 C20 . . . . 176.3(3) no
C18 C17 C21 C20 . . . . -2.1(5) no
C15 C16 N3 C13 . . . . 62.6(4) no
C14 C13 N3 C16 . . . . -63.3(4) no
C21 C17 N4 C15 . . . . 8.9(5) no
C18 C17 N4 C15 . . . . -172.8(3) no
C21 C17 N4 C14 . . . . 159.0(3) no
C18 C17 N4 C14 . . . . -22.7(5) no
C16 C15 N4 C17 . . . . -164.1(3) no
C16 C15 N4 C14 . . . . 44.3(5) no
C13 C14 N4 C17 . . . . 163.7(3) no
C13 C14 N4 C15 . . . . -44.8(5) no
C18 C19 N5 C20 . . . . -1.9(6) no
C21 C20 N5 C19 . . . . 1.9(6) no
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 2097643'
loop_
_audit_author_name
_audit_author_address
'Zhao Chenyang'
;Tianjin University
China
;
_audit_update_record             
;
2021-07-20 deposited with the CCDC.	2021-08-19 downloaded from the CCDC.
;
_audit_creation_date             2018-10-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'DAP-PYR (2:1)'
_chemical_formula_moiety         '2(C12 H12 N2 O2 S), C9 H13 N3'
_chemical_formula_sum            'C33 H37 N7 O4 S2'
_chemical_formula_weight         659.81
_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                   5.7687(12)
_cell_length_b                   7.8235(16)
_cell_length_c                   35.517(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.67(3)
_cell_angle_gamma                90
_cell_volume                     1602.3(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3789
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9344
_cell_measurement_theta_min      2.2947
_shelx_estimated_absorpt_T_max   0.974
_shelx_estimated_absorpt_T_min   0.958
_exptl_absorpt_coefficient_mu    0.216
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7682
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   crystalclear
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       46
_diffrn_reflns_limit_l_min       -46
_diffrn_reflns_number            16270
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.901
_diffrn_reflns_theta_min         2.845
_diffrn_ambient_temperature      113.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'rigaku saturn 70 CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2925
_reflns_number_total             3813
_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       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        crystalclear
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.330
_refine_diff_density_min         -0.349
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         3813
_refine_ls_number_restraints     156
_refine_ls_R_factor_all          0.0645
_refine_ls_R_factor_gt           0.0481
_refine_ls_restrained_S_all      1.079
_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)+(0.0573P)²+0.1873P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1123
_refine_ls_wR_factor_ref         0.1227
_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, All N(H,H) groups
2. Restrained distances
 N1-H1A = N1-H1B = N2-H2A = N2-H2B
 0.9 with sigma of 0.01
 H1A-H1B = H2A-H2B
 1.5 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
N3 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17 \\sim N4 \\sim C18 \\sim
C19 \\sim N5 \\sim C20 \\sim C21: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(N3) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C15)
\\sim Ueq, Uanis(C16) \\sim Ueq, Uanis(C17) \\sim Ueq, Uanis(N4) \\sim Ueq,
Uanis(C18) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(N5) \\sim Ueq, Uanis(C20)
\\sim Ueq, Uanis(C21) \\sim Ueq: with sigma of 0.01 and sigma for terminal
atoms of 0.02
4. Others
 Fixed Sof: N3(0.5) C13(0.5) H13(0.5) C14(0.5) H14(0.5) C15(0.5) C16(0.5)
 H16(0.5) C17(0.5) H17(0.5) N4(0.5) C19(0.5) H19A(0.5) H19B(0.5) C18(0.5)
 H18A(0.5) H18B(0.5) N5(0.5) H5A(0.5) C21(0.5) H21A(0.5) H21B(0.5) C20(0.5)
 H20A(0.5) H20B(0.5)
5.a Riding coordinates:
 N5(H5A)
5.b Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C18(H18A,H18B), C21(H21A,H21B), C20(H20A,H20B)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C11(H11), C12(H12), C13(H13),
 C14(H14), C16(H16), C17(H17)
5.d Fitted hexagon refined as free rotating group:
 N3(C13,C14,C15,C16,C17)
;
_atom_sites_solution_hydrogens   mixed
_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 0.59971(8) 0.44683(6) 0.16202(2) 0.02765(14) Uani 1 1 d . . . . .
O1 O 0.8481(2) 0.42861(16) 0.15820(4) 0.0341(3) Uani 1 1 d . . . . .
O2 O 0.4530(2) 0.30907(16) 0.14861(4) 0.0355(3) Uani 1 1 d . . . . .
N1 N 0.4294(3) 0.5583(2) 0.32412(4) 0.0344(4) Uani 1 1 d D . . . .
H1A H 0.508(3) 0.6457(19) 0.3340(5) 0.041 Uiso 1 1 d DR . . . .
H1B H 0.2807(18) 0.550(2) 0.3303(6) 0.041 Uiso 1 1 d DR . . . .
N2 N 0.3104(3) 1.0763(2) 0.08192(5) 0.0399(4) Uani 1 1 d D . . . .
H2A H 0.167(2) 1.083(2) 0.0726(6) 0.048 Uiso 1 1 d DR . . . .
H2B H 0.372(3) 1.1707(18) 0.0915(6) 0.048 Uiso 1 1 d DR . . . .
C1 C 0.4666(3) 0.5309(2) 0.28624(5) 0.0270(4) Uani 1 1 d . . . . .
C2 C 0.3024(3) 0.4466(2) 0.26306(5) 0.0296(4) Uani 1 1 d . . . . .
H2 H 0.163260 0.405346 0.273456 0.036 Uiso 1 1 calc R . . . .
C3 C 0.3413(3) 0.4230(2) 0.22524(5) 0.0287(4) Uani 1 1 d . . . . .
H3 H 0.227085 0.368514 0.209619 0.034 Uiso 1 1 calc R . . . .
C4 C 0.5473(3) 0.4788(2) 0.20996(5) 0.0247(4) Uani 1 1 d . . . . .
C5 C 0.7153(3) 0.5594(2) 0.23286(5) 0.0289(4) Uani 1 1 d . . . . .
H5 H 0.856554 0.597084 0.222548 0.035 Uiso 1 1 calc R . . . .
C6 C 0.6744(3) 0.5839(2) 0.27056(5) 0.0306(4) Uani 1 1 d . . . . .
H6 H 0.789471 0.637600 0.286160 0.037 Uiso 1 1 calc R . . . .
C7 C 0.5117(3) 0.6330(2) 0.13846(5) 0.0261(4) Uani 1 1 d . . . . .
C8 C 0.2968(3) 0.6398(2) 0.11988(5) 0.0309(4) Uani 1 1 d . . . . .
H8 H 0.196169 0.543715 0.120185 0.037 Uiso 1 1 calc R . . . .
C9 C 0.2297(3) 0.7868(3) 0.10094(5) 0.0317(4) Uani 1 1 d . . . . .
H9 H 0.084117 0.789939 0.087731 0.038 Uiso 1 1 calc R . . . .
C10 C 0.3729(3) 0.9309(2) 0.10094(5) 0.0288(4) Uani 1 1 d . . . . .
C11 C 0.5880(3) 0.9224(2) 0.12024(6) 0.0338(4) Uani 1 1 d . . . . .
H11 H 0.687839 1.018956 0.120437 0.041 Uiso 1 1 calc R . . . .
C12 C 0.6565(3) 0.7756(2) 0.13894(5) 0.0315(4) Uani 1 1 d . . . . .
H12 H 0.802076 0.771732 0.152130 0.038 Uiso 1 1 calc R . . . .
N3 N 0.8685(11) 0.1785(8) 0.0428(2) 0.0305(15) Uani 0.5 1 d . U P A -1
C13 C 0.8297(11) 0.3314(9) 0.06151(14) 0.0410(17) Uani 0.5 1 d G U P A -1
H13 H 0.908221 0.354154 0.084854 0.049 Uiso 0.5 1 calc R . P A -1
C14 C 0.6761(12) 0.4509(7) 0.04608(15) 0.0365(18) Uani 0.5 1 d G U P A -1
H14 H 0.649608 0.555411 0.058879 0.044 Uiso 0.5 1 calc R . P A -1
C15 C 0.5612(10) 0.4176(7) 0.01192(15) 0.0299(13) Uani 0.5 1 d G U P A -1
C16 C 0.6000(13) 0.2647(9) -0.00681(17) 0.044(3) Uani 0.5 1 d G U P A -1
H16 H 0.521456 0.241862 -0.030153 0.053 Uiso 0.5 1 calc R . P A -1
C17 C 0.7536(15) 0.1451(8) 0.0086(2) 0.042(2) Uani 0.5 1 d G U P A -1
H17 H 0.780068 0.040602 -0.004178 0.050 Uiso 0.5 1 calc R . P A -1
N4 N 0.4035(9) 0.5359(6) -0.00366(14) 0.0301(11) Uani 0.5 1 d . U P A -1
C19 C 0.1271(13) 0.6348(10) -0.05331(18) 0.0443(17) Uani 0.5 1 d . U P A -1
H19A H 0.088293 0.620387 -0.080456 0.053 Uiso 0.5 1 calc R . P A -1
H19B H -0.009731 0.597878 -0.039217 0.053 Uiso 0.5 1 calc R . P A -1
C18 C 0.3256(16) 0.5169(12) -0.0432(2) 0.047(2) Uani 0.5 1 d . U P A -1
H18A H 0.276445 0.397225 -0.047673 0.056 Uiso 0.5 1 calc R . P A -1
H18B H 0.456778 0.541409 -0.059680 0.056 Uiso 0.5 1 calc R . P A -1
N5 N 0.1635(15) 0.8091(11) -0.0463(3) 0.048(2) Uani 0.5 1 d . U P A -1
H5A H 0.048696 0.875385 -0.054175 0.058 Uiso 0.5 1 d R . P A -1
C21 C 0.4263(16) 0.7214(10) 0.0053(2) 0.038(2) Uani 0.5 1 d . U P A -1
H21A H 0.448498 0.735613 0.032907 0.045 Uiso 0.5 1 calc R . P A -1
H21B H 0.565190 0.767626 -0.006827 0.045 Uiso 0.5 1 calc R . P A -1
C20 C 0.2192(18) 0.8199(11) -0.0077(3) 0.047(2) Uani 0.5 1 d . U P A -1
H20A H 0.084138 0.779635 0.006459 0.057 Uiso 0.5 1 calc R . P A -1
H20B H 0.244355 0.941656 -0.001115 0.057 Uiso 0.5 1 calc R . P A -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 O1 1.4502(13) . ?
S1 O2 1.4428(13) . ?
S1 C4 1.7557(18) . ?
S1 C7 1.7475(19) . ?
N1 H1A 0.886(9) . ?
N1 H1B 0.894(9) . ?
N1 C1 1.385(2) . ?
N2 H2A 0.884(9) . ?
N2 H2B 0.882(9) . ?
N2 C10 1.367(2) . ?
C1 C2 1.401(3) . ?
C1 C6 1.399(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.381(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.391(2) . ?
C4 C5 1.397(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.380(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.388(2) . ?
C7 C12 1.394(2) . ?
C8 H8 0.9500 . ?
C8 C9 1.382(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.398(3) . ?
C10 C11 1.402(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.378(3) . ?
C12 H12 0.9500 . ?
N3 C13 1.3900 . ?
N3 C17 1.3900 . ?
C13 H13 0.9500 . ?
C13 C14 1.3900 . ?
C14 H14 0.9500 . ?
C14 C15 1.3900 . ?
C15 C16 1.3900 . ?
C15 N4 1.401(4) . ?
C16 H16 0.9500 . ?
C16 C17 1.3900 . ?
C17 H17 0.9500 . ?
N4 C18 1.468(7) . ?
N4 C21 1.491(7) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C19 C18 1.506(7) . ?
C19 N5 1.401(8) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
N5 H5A 0.8799 . ?
N5 C20 1.404(7) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C20 1.484(7) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?

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
O1 S1 C4 107.66(8) . . ?
O1 S1 C7 108.13(8) . . ?
O2 S1 O1 117.87(8) . . ?
O2 S1 C4 108.10(8) . . ?
O2 S1 C7 107.75(8) . . ?
C7 S1 C4 106.84(8) . . ?
H1A N1 H1B 116.0(14) . . ?
C1 N1 H1A 114.5(13) . . ?
C1 N1 H1B 113.9(13) . . ?
H2A N2 H2B 117.2(14) . . ?
C10 N2 H2A 117.5(14) . . ?
C10 N2 H2B 114.2(13) . . ?
N1 C1 C2 121.49(17) . . ?
N1 C1 C6 119.95(17) . . ?
C6 C1 C2 118.54(17) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.55(17) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.17(17) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 S1 120.46(14) . . ?
C3 C4 C5 120.02(16) . . ?
C5 C4 S1 119.52(14) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 C4 119.50(17) . . ?
C6 C5 H5 120.3 . . ?
C1 C6 H6 119.4 . . ?
C5 C6 C1 121.17(17) . . ?
C5 C6 H6 119.4 . . ?
C8 C7 S1 120.17(14) . . ?
C8 C7 C12 120.10(17) . . ?
C12 C7 S1 119.72(14) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 C7 119.81(17) . . ?
C9 C8 H8 120.1 . . ?
C8 C9 H9 119.5 . . ?
C8 C9 C10 120.92(17) . . ?
C10 C9 H9 119.5 . . ?
N2 C10 C9 121.62(17) . . ?
N2 C10 C11 119.88(17) . . ?
C9 C10 C11 118.48(17) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 C10 120.83(17) . . ?
C12 C11 H11 119.6 . . ?
C7 C12 H12 120.1 . . ?
C11 C12 C7 119.85(17) . . ?
C11 C12 H12 120.1 . . ?
C13 N3 C17 120.0 . . ?
N3 C13 H13 120.0 . . ?
C14 C13 N3 120.0 . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 120.0 . . ?
C13 C14 C15 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 N4 120.6(3) . . ?
C16 C15 C14 120.0 . . ?
C16 C15 N4 119.4(3) . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.0 . . ?
C17 C16 H16 120.0 . . ?
N3 C17 H17 120.0 . . ?
C16 C17 N3 120.0 . . ?
C16 C17 H17 120.0 . . ?
C15 N4 C18 119.2(4) . . ?
C15 N4 C21 120.4(4) . . ?
C18 N4 C21 109.0(5) . . ?
H19A C19 H19B 107.3 . . ?
C18 C19 H19A 108.2 . . ?
C18 C19 H19B 108.2 . . ?
N5 C19 H19A 108.2 . . ?
N5 C19 H19B 108.2 . . ?
N5 C19 C18 116.4(5) . . ?
N4 C18 C19 112.1(5) . . ?
N4 C18 H18A 109.2 . . ?
N4 C18 H18B 109.2 . . ?
C19 C18 H18A 109.2 . . ?
C19 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C19 N5 H5A 114.2 . . ?
C19 N5 C20 105.1(6) . . ?
C20 N5 H5A 115.1 . . ?
N4 C21 H21A 109.2 . . ?
N4 C21 H21B 109.2 . . ?
H21A C21 H21B 107.9 . . ?
C20 C21 N4 112.0(5) . . ?
C20 C21 H21A 109.2 . . ?
C20 C21 H21B 109.2 . . ?
N5 C20 C21 115.6(5) . . ?
N5 C20 H20A 108.4 . . ?
N5 C20 H20B 108.4 . . ?
C21 C20 H20A 108.4 . . ?
C21 C20 H20B 108.4 . . ?
H20A C20 H20B 107.4 . . ?

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
S1 C4 C5 C6 -179.71(14) . . . . ?
S1 C7 C8 C9 -179.24(14) . . . . ?
S1 C7 C12 C11 179.72(15) . . . . ?
O1 S1 C4 C3 -149.73(14) . . . . ?
O1 S1 C4 C5 29.60(16) . . . . ?
O1 S1 C7 C8 145.12(14) . . . . ?
O1 S1 C7 C12 -36.01(16) . . . . ?
O2 S1 C4 C3 -21.41(17) . . . . ?
O2 S1 C4 C5 157.92(14) . . . . ?
O2 S1 C7 C8 16.71(17) . . . . ?
O2 S1 C7 C12 -164.42(14) . . . . ?
N1 C1 C2 C3 178.94(16) . . . . ?
N1 C1 C6 C5 -179.46(16) . . . . ?
N2 C10 C11 C12 -178.63(18) . . . . ?
C1 C2 C3 C4 1.7(3) . . . . ?
C2 C1 C6 C5 2.2(3) . . . . ?
C2 C3 C4 S1 179.16(14) . . . . ?
C2 C3 C4 C5 -0.2(3) . . . . ?
C3 C4 C5 C6 -0.4(3) . . . . ?
C4 S1 C7 C8 -99.25(16) . . . . ?
C4 S1 C7 C12 79.63(16) . . . . ?
C4 C5 C6 C1 -0.6(3) . . . . ?
C6 C1 C2 C3 -2.7(3) . . . . ?
C7 S1 C4 C3 94.32(16) . . . . ?
C7 S1 C4 C5 -86.35(15) . . . . ?
C7 C8 C9 C10 -1.6(3) . . . . ?
C8 C7 C12 C11 -1.4(3) . . . . ?
C8 C9 C10 N2 179.09(18) . . . . ?
C8 C9 C10 C11 0.8(3) . . . . ?
C9 C10 C11 C12 -0.3(3) . . . . ?
C10 C11 C12 C7 0.6(3) . . . . ?
C12 C7 C8 C9 1.9(3) . . . . ?
N3 C13 C14 C15 0.0 . . . . ?
C13 N3 C17 C16 0.0 . . . . ?
C13 C14 C15 C16 0.0 . . . . ?
C13 C14 C15 N4 179.1(5) . . . . ?
C14 C15 C16 C17 0.0 . . . . ?
C14 C15 N4 C18 166.2(6) . . . . ?
C14 C15 N4 C21 26.6(8) . . . . ?
C15 C16 C17 N3 0.0 . . . . ?
C15 N4 C18 C19 170.0(5) . . . . ?
C15 N4 C21 C20 -168.9(5) . . . . ?
C16 C15 N4 C18 -14.8(9) . . . . ?
C16 C15 N4 C21 -154.3(7) . . . . ?
C17 N3 C13 C14 0.0 . . . . ?
N4 C15 C16 C17 -179.1(5) . . . . ?
N4 C21 C20 N5 -57.8(8) . . . . ?
C19 N5 C20 C21 59.0(8) . . . . ?
C18 N4 C21 C20 47.9(7) . . . . ?
C18 C19 N5 C20 -57.5(8) . . . . ?
N5 C19 C18 N4 55.0(9) . . . . ?
C21 N4 C18 C19 -46.2(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
