# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# 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_5-msal_a
_database_code_depnum_ccdc_archive 'CCDC 1975393'
loop_
_audit_author_name
_audit_author_address
'Kerem Kaya'
;Istanbul Technical University, Chemistry Department
Turkey
;
_audit_update_record             
;
2020-10-01 deposited with the CCDC.	2020-11-04 downloaded from the CCDC.
;
_audit_creation_date             2020-09-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         'C24 H23 N3 O3 S'
_chemical_formula_sum            'C24 H23 N3 O3 S'
_chemical_formula_weight         433.53
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   8.569(2)
_cell_length_b                   11.153(3)
_cell_length_c                   12.207(3)
_cell_angle_alpha                101.257(9)
_cell_angle_beta                 91.058(9)
_cell_angle_gamma                110.621(9)
_cell_volume                     1066.1(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    24
_cell_measurement_temperature    305(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      5
_exptl_crystal_description       rod_like
_exptl_absorpt_coefficient_mu    0.184
_exptl_crystal_density_diffrn    1.3505
_exptl_crystal_F_000             456.4467
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.2
_exptl_crystal_colour            orange
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_av_unetI/netI     0.0329
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            42764
_diffrn_reflns_theta_full        26.5755
_diffrn_reflns_theta_max         26.58
_diffrn_reflns_theta_min         2.33
_diffrn_ambient_temperature      303.0
_diffrn_measured_fraction_theta_full 0.9904
_diffrn_measured_fraction_theta_max 0.9904
_diffrn_measurement_device_type  Bruker_D8_VENTURE
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              13
_reflns_limit_k_min              -14
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                3188
_reflns_number_total             4415
_reflns_threshold_expression     I>=2u(I)
_computing_data_collection       'APEX-II (Bruker, 2004)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_refine_diff_density_max         0.3095
_refine_diff_density_min         -0.2614
_refine_diff_density_rms         0.0649
_refine_ls_d_res_high            0.7943
_refine_ls_d_res_low             8.7316
_refine_ls_goodness_of_fit_ref   1.0825
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    38
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4415
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0724
_refine_ls_R_factor_gt           0.0456
_refine_ls_restrained_S_all      1.0825
_refine_ls_shift/su_max          0.0032
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0572P)²+0.3042P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1126
_refine_ls_wR_factor_ref         0.1297
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C4(H4a,H4b), C2(H2a,H2b)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C17(H17), C19(H19), C6(H6), C11(H11), C15(H15), C22(H22),
 C21(H21)
2.c Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c), C3(H3a,H3b,H3c), C24(H24a,H24b,H24c)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
S1 S 0.85032(7) 0.87220(5) 0.55833(5) 0.05333(19) Uani 1.000000 .
O3 O 0.40826(16) 0.43032(12) 0.76403(11) 0.0430(3) Uani 1.000000 .
O1 O 1.1341(2) 0.87817(14) 0.23664(14) 0.0622(4) Uani 1.000000 .
H1 H 1.081(3) 0.8687(8) 0.2916(15) 0.0933(6) Uiso 1.000000 GR
O2 O 0.4723(2) 0.63991(14) 0.77029(13) 0.0608(4) Uani 1.000000 .
N2 N 0.78739(19) 0.62489(15) 0.50343(13) 0.0393(4) Uani 1.000000 .
N3 N 0.96555(19) 0.75026(15) 0.38401(13) 0.0427(4) Uani 1.000000 .
N1 N 0.2823(2) -0.01058(16) 0.79828(15) 0.0532(5) Uani 1.000000 .
C10 C 0.5302(2) 0.29867(17) 0.64113(15) 0.0378(4) Uani 1.000000 .
C9 C 0.4262(2) 0.31128(17) 0.72547(15) 0.0371(4) Uani 1.000000 .
C13 C 0.6072(2) 0.53030(17) 0.63951(14) 0.0368(4) Uani 1.000000 .
C14 C 0.7038(2) 0.64581(18) 0.59664(15) 0.0381(4) Uani 1.000000 .
C18 C 1.0758(2) 0.64876(19) 0.22873(16) 0.0412(4) Uani 1.000000 .
C16 C 0.8685(2) 0.73484(18) 0.47463(16) 0.0400(4) Uani 1.000000 .
C12 C 0.4967(2) 0.54201(18) 0.72656(16) 0.0413(4) Uani 1.000000 .
C7 C 0.4611(2) 0.07350(18) 0.65730(17) 0.0456(5) Uani 1.000000 .
H7 H 0.4725(2) -0.00711(18) 0.63304(17) 0.0547(6) Uiso 1.000000 R
C8 C 0.5436(2) 0.17511(18) 0.60864(16) 0.0437(5) Uani 1.000000 .
H8 H 0.6110(2) 0.16227(18) 0.55208(16) 0.0524(6) Uiso 1.000000 R
C5 C 0.3579(2) 0.08855(18) 0.74438(16) 0.0423(4) Uani 1.000000 .
C17 C 0.9819(2) 0.64665(19) 0.32535(16) 0.0434(5) Uani 1.000000 .
H17 H 0.9309(2) 0.56708(19) 0.34641(16) 0.0521(5) Uiso 1.000000 R
C19 C 1.0982(2) 0.5335(2) 0.17420(16) 0.0466(5) Uani 1.000000 .
H19 H 1.0481(2) 0.4571(2) 0.20024(16) 0.0559(6) Uiso 1.000000 R
C6 C 0.3391(2) 0.21058(18) 0.77524(16) 0.0429(5) Uani 1.000000 .
H6 H 0.2679(2) 0.22298(18) 0.82923(16) 0.0515(5) Uiso 1.000000 R
C11 C 0.6185(2) 0.41110(18) 0.59934(15) 0.0391(4) Uani 1.000000 .
H11 H 0.6870(2) 0.40334(18) 0.54223(15) 0.0469(5) Uiso 1.000000 R
C25 C 1.1501(2) 0.7630(2) 0.18843(17) 0.0460(5) Uani 1.000000 .
C15 C 0.7245(3) 0.77400(19) 0.63703(17) 0.0467(5) Uani 1.000000 .
H15 H 0.6763(3) 0.80375(19) 0.69915(17) 0.0560(6) Uiso 1.000000 R
C20 C 1.1911(3) 0.5293(2) 0.08393(17) 0.0502(5) Uani 1.000000 .
C22 C 1.2420(3) 0.7587(2) 0.09667(19) 0.0597(6) Uani 1.000000 .
H22 H 1.2906(3) 0.8340(2) 0.06881(19) 0.0716(7) Uiso 1.000000 R
C4 C 0.3119(3) -0.13426(19) 0.77386(19) 0.0528(5) Uani 1.000000 .
H4a H 0.4261(3) -0.11687(19) 0.75487(19) 0.0634(6) Uiso 1.000000 R
H4b H 0.2997(3) -0.17037(19) 0.84072(19) 0.0634(6) Uiso 1.000000 R
C2 C 0.1806(3) 0.0065(2) 0.8904(2) 0.0608(6) Uani 1.000000 .
H2a H 0.1117(3) 0.0537(2) 0.8715(2) 0.0729(7) Uiso 1.000000 R
H2b H 0.1063(3) -0.0792(2) 0.8987(2) 0.0729(7) Uiso 1.000000 R
C21 C 1.2621(3) 0.6446(2) 0.04642(19) 0.0585(6) Uani 1.000000 .
H21 H 1.3254(3) 0.6445(2) -0.01469(19) 0.0702(7) Uiso 1.000000 R
C1 C 0.2829(4) 0.0799(2) 1.0012(2) 0.0737(7) Uani 1.000000 .
H1a H 0.3578(17) 0.0376(11) 1.0179(8) 0.1105(11) Uiso 1.000000 GR
H1b H 0.3465(18) 0.1686(6) 0.9966(5) 0.1105(11) Uiso 1.000000 GR
H1c H 0.2093(4) 0.0802(16) 1.0596(3) 0.1105(11) Uiso 1.000000 GR
C3 C 0.1933(3) -0.2344(2) 0.6787(2) 0.0696(7) Uani 1.000000 .
H3a H 0.0802(4) -0.2544(13) 0.6981(6) 0.1043(10) Uiso 1.000000 GR
H3b H 0.2054(16) -0.1996(7) 0.6121(4) 0.1043(10) Uiso 1.000000 GR
H3c H 0.2189(15) -0.3129(7) 0.6655(10) 0.1043(10) Uiso 1.000000 GR
C24 C 1.2172(3) 0.4056(3) 0.0291(2) 0.0721(7) Uani 1.000000 .
H24a H 1.3315(7) 0.4153(7) 0.0458(13) 0.1082(11) Uiso 1.000000 GR
H24b H 1.1441(16) 0.3332(4) 0.0572(11) 0.1082(11) Uiso 1.000000 GR
H24c H 1.193(2) 0.3895(10) -0.0506(2) 0.1082(11) Uiso 1.000000 GR


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 C16 1.7256(19) . ?
S1 C15 1.704(2) . ?
O3 C9 1.382(2) . ?
O3 C12 1.380(2) . ?
O1 H1 0.8200 . ?
O1 C25 1.359(2) . ?
O2 C12 1.207(2) . ?
N2 C14 1.380(2) . ?
N2 C16 1.299(2) . ?
N3 C16 1.397(2) . ?
N3 C17 1.290(2) . ?
N1 C5 1.368(2) . ?
N1 C4 1.464(2) . ?
N1 C2 1.459(3) . ?
C10 C9 1.393(3) . ?
C10 C8 1.403(3) . ?
C10 C11 1.414(3) . ?
C9 C6 1.371(3) . ?
C13 C14 1.465(3) . ?
C13 C12 1.454(3) . ?
C13 C11 1.362(2) . ?
C14 C15 1.364(3) . ?
C18 C17 1.439(3) . ?
C18 C19 1.406(3) . ?
C18 C25 1.399(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.360(3) . ?
C7 C5 1.417(3) . ?
C8 H8 0.9300 . ?
C5 C6 1.406(3) . ?
C17 H17 0.9300 . ?
C19 H19 0.9300 . ?
C19 C20 1.375(3) . ?
C6 H6 0.9300 . ?
C11 H11 0.9300 . ?
C25 C22 1.384(3) . ?
C15 H15 0.9300 . ?
C20 C21 1.387(3) . ?
C20 C24 1.504(3) . ?
C22 H22 0.9300 . ?
C22 C21 1.371(3) . ?
C4 H4a 0.9700 . ?
C4 H4b 0.9700 . ?
C4 C3 1.510(3) . ?
C2 H2a 0.9700 . ?
C2 H2b 0.9700 . ?
C2 C1 1.513(3) . ?
C21 H21 0.9300 . ?
C1 H1a 0.9600 . ?
C1 H1b 0.9600 . ?
C1 H1c 0.9600 . ?
C3 H3a 0.9600 . ?
C3 H3b 0.9600 . ?
C3 H3c 0.9600 . ?
C24 H24a 0.9600 . ?
C24 H24b 0.9600 . ?
C24 H24c 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
C15 S1 C16 88.98(9) . . ?
C12 O3 C9 122.72(14) . . ?
C25 O1 H1 109.5 . . ?
C16 N2 C14 110.73(16) . . ?
C17 N3 C16 117.37(16) . . ?
C4 N1 C5 121.78(17) . . ?
C2 N1 C5 121.43(16) . . ?
C2 N1 C4 116.55(16) . . ?
C8 C10 C9 116.21(17) . . ?
C11 C10 C9 118.10(16) . . ?
C11 C10 C8 125.62(17) . . ?
C10 C9 O3 120.04(16) . . ?
C6 C9 O3 116.58(15) . . ?
C6 C9 C10 123.37(16) . . ?
C12 C13 C14 119.83(16) . . ?
C11 C13 C14 121.28(16) . . ?
C11 C13 C12 118.90(16) . . ?
C13 C14 N2 116.97(16) . . ?
C15 C14 N2 114.35(17) . . ?
C15 C14 C13 128.67(17) . . ?
C19 C18 C17 119.40(17) . . ?
C25 C18 C17 122.22(18) . . ?
C25 C18 C19 118.37(18) . . ?
N2 C16 S1 115.08(14) . . ?
N3 C16 S1 118.70(13) . . ?
N3 C16 N2 126.22(17) . . ?
O2 C12 O3 115.45(16) . . ?
C13 C12 O3 117.60(15) . . ?
C13 C12 O2 126.94(17) . . ?
C8 C7 H7 119.48(11) . . ?
C5 C7 H7 119.48(11) . . ?
C5 C7 C8 121.05(17) . . ?
C7 C8 C10 122.06(17) . . ?
H8 C8 C10 118.97(11) . . ?
H8 C8 C7 118.97(11) . . ?
C7 C5 N1 121.47(17) . . ?
C6 C5 N1 121.06(17) . . ?
C6 C5 C7 117.46(17) . . ?
C18 C17 N3 122.88(17) . . ?
H17 C17 N3 118.56(11) . . ?
H17 C17 C18 118.56(11) . . ?
H19 C19 C18 118.68(11) . . ?
C20 C19 C18 122.64(19) . . ?
C20 C19 H19 118.68(13) . . ?
C5 C6 C9 119.78(17) . . ?
H6 C6 C9 120.11(11) . . ?
H6 C6 C5 120.11(11) . . ?
C13 C11 C10 122.55(17) . . ?
H11 C11 C10 118.73(10) . . ?
H11 C11 C13 118.73(11) . . ?
C18 C25 O1 121.83(18) . . ?
C22 C25 O1 119.01(18) . . ?
C22 C25 C18 119.16(19) . . ?
C14 C15 S1 110.86(15) . . ?
H15 C15 S1 124.57(7) . . ?
H15 C15 C14 124.57(11) . . ?
C21 C20 C19 117.1(2) . . ?
C24 C20 C19 121.6(2) . . ?
C24 C20 C21 121.3(2) . . ?
H22 C22 C25 119.65(13) . . ?
C21 C22 C25 120.7(2) . . ?
C21 C22 H22 119.65(13) . . ?
H4a C4 N1 109.03(11) . . ?
H4b C4 N1 109.03(11) . . ?
H4b C4 H4a 107.8 . . ?
C3 C4 N1 112.80(18) . . ?
C3 C4 H4a 109.03(14) . . ?
C3 C4 H4b 109.03(13) . . ?
H2a C2 N1 108.87(11) . . ?
H2b C2 N1 108.87(11) . . ?
H2b C2 H2a 107.7 . . ?
C1 C2 N1 113.5(2) . . ?
C1 C2 H2a 108.87(13) . . ?
C1 C2 H2b 108.87(12) . . ?
C22 C21 C20 122.0(2) . . ?
H21 C21 C20 119.00(13) . . ?
H21 C21 C22 119.00(13) . . ?
H1a C1 C2 109.5 . . ?
H1b C1 C2 109.5 . . ?
H1b C1 H1a 109.5 . . ?
H1c C1 C2 109.5 . . ?
H1c C1 H1a 109.5 . . ?
H1c C1 H1b 109.5 . . ?
H3a C3 C4 109.5 . . ?
H3b C3 C4 109.5 . . ?
H3b C3 H3a 109.5 . . ?
H3c C3 C4 109.5 . . ?
H3c C3 H3a 109.5 . . ?
H3c C3 H3b 109.5 . . ?
H24a C24 C20 109.5 . . ?
H24b C24 C20 109.5 . . ?
H24b C24 H24a 109.5 . . ?
H24c C24 C20 109.5 . . ?
H24c C24 H24a 109.5 . . ?
H24c C24 H24b 109.5 . . ?

_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_nn4meo_a
_database_code_depnum_ccdc_archive 'CCDC 1975395'
loop_
_audit_author_name
_audit_author_address
'Kerem Kaya'
;Istanbul Technical University, Chemistry Department
Turkey
;
_audit_update_record             
;
2020-10-01 deposited with the CCDC.	2020-11-04 downloaded from the CCDC.
;
_audit_creation_date             2020-09-18
_audit_creation_method           
;
Olex2 1.3-dev
(compiled 2020.09.11 svn.rc89507dd for OlexSys, GUI svn.r5830)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H23 N3 O4 S'
_chemical_formula_sum            'C24 H23 N3 O4 S'
_chemical_formula_weight         449.51
_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      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                   8.0871(5)
_cell_length_b                   8.3785(5)
_cell_length_c                   16.9875(10)
_cell_angle_alpha                98.318(3)
_cell_angle_beta                 91.468(3)
_cell_angle_gamma                105.343(3)
_cell_volume                     1095.87(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    24
_cell_measurement_temperature    305(2)
_cell_measurement_theta_max      25
_cell_measurement_theta_min      2.43
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.185
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   Multi_Scan
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            dark_yellow
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       square
_exptl_crystal_F_000             472
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.02
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0174
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            44296
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_min         2.429
_diffrn_ambient_temperature      305.2
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  Bruker_D8_Venture
_diffrn_measurement_method       'ω and phi scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_exptl_transmission_factor_min   0.880
_exptl_transmission_factor_max   0.972
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3763
_reflns_number_total             4799
_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       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2 V2014.11-0'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.3-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.046
_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     313
_refine_ls_number_reflns         4799
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0391
_refine_ls_restrained_S_all      1.036
_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)+(0.0529P)²+0.2367P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1079
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 N1-C23 \\sim N1-C23A
 with sigma of 0.02
 N1-C24 \\sim N1-C24A
 with sigma of 0.04
 C23-C24 \\sim C23A-C24A
 with sigma of 0.02
3. Others
 Sof(C23A)=Sof(H23C)=Sof(H23D)=Sof(C24A)=Sof(H24D)=Sof(H24E)=Sof(H24F)=1-FVAR(1)
 Sof(C23)=Sof(H23A)=Sof(H23B)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(H24C)=FVAR(1)
4.a Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C23(H23A,H23B), C23A(H23C,H23D)
4.b Aromatic/amide H refined with riding coordinates:
 C14(H14), C19(H19), C17(H17), C18(H18), C8(H8), C10(H10), C7(H7), C4(H4),
 C2(H2A)
4.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C1(H1A,H1B,H1C), C24(H24A,H24B,H24C), C24A(H24D,H24E,H24F)
4.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
S S 0.62363(5) 0.79470(5) 0.32024(3) 0.05708(14) Uani 1 1 d . . . . .
O4 O 0.22907(12) 0.63073(11) 0.60960(6) 0.0431(2) Uani 1 1 d . . . . .
O3 O 0.43344(16) 0.82585(12) 0.57043(7) 0.0603(3) Uani 1 1 d . . . . .
N3 N 0.58091(16) 0.49822(17) 0.22599(8) 0.0512(3) Uani 1 1 d . . . . .
N2 N 0.44162(15) 0.51106(15) 0.34916(7) 0.0439(3) Uani 1 1 d . . . . .
O2 O 0.6537(2) 0.46667(17) 0.07542(8) 0.0800(4) Uani 1 1 d . . . . .
H2 H 0.626216 0.511333 0.117367 0.120 Uiso 1 1 calc R U . . .
C15 C 0.10737(16) 0.36293(15) 0.52940(8) 0.0353(3) Uani 1 1 d . . . . .
N1 N -0.14683(19) 0.20882(17) 0.72943(8) 0.0594(4) Uani 1 1 d D . . . .
C12 C 0.32543(16) 0.57406(16) 0.47740(8) 0.0380(3) Uani 1 1 d . . . . .
C16 C 0.12151(17) 0.47087(15) 0.60114(8) 0.0368(3) Uani 1 1 d . . . . .
O1 O 0.7745(2) -0.02477(18) -0.04104(8) 0.0845(4) Uani 1 1 d . . . . .
C14 C 0.21254(17) 0.41976(16) 0.46823(8) 0.0377(3) Uani 1 1 d . . . . .
H14 H 0.203885 0.348683 0.419987 0.045 Uiso 1 1 calc R U . . .
C13 C 0.33813(18) 0.68673(16) 0.55215(8) 0.0421(3) Uani 1 1 d . . . . .
C19 C 0.03422(18) 0.42616(17) 0.66626(8) 0.0420(3) Uani 1 1 d . . . . .
H19 H 0.045618 0.503912 0.712438 0.050 Uiso 1 1 calc R U . . .
C17 C -0.01102(17) 0.20504(16) 0.52480(8) 0.0394(3) Uani 1 1 d . . . . .
H17 H -0.030554 0.131809 0.476752 0.047 Uiso 1 1 calc R U . . .
C11 C 0.43373(17) 0.63018(17) 0.41336(9) 0.0412(3) Uani 1 1 d . . . . .
C20 C -0.07257(18) 0.26246(18) 0.66302(8) 0.0422(3) Uani 1 1 d . . . . .
C6 C 0.63365(18) 0.2502(2) 0.15622(9) 0.0480(3) Uani 1 1 d . . . . .
C18 C -0.09846(18) 0.15559(16) 0.58874(8) 0.0411(3) Uani 1 1 d . . . . .
H18 H -0.176177 0.050041 0.583318 0.049 Uiso 1 1 calc R U . . .
C9 C 0.53813(18) 0.58079(19) 0.29675(9) 0.0468(3) Uani 1 1 d . . . . .
C8 C 0.58526(18) 0.3452(2) 0.22408(9) 0.0480(4) Uani 1 1 d . . . . .
H8 H 0.555612 0.294395 0.268806 0.058 Uiso 1 1 calc R U . . .
C10 C 0.52602(19) 0.78922(19) 0.40778(10) 0.0501(4) Uani 1 1 d . . . . .
H10 H 0.534530 0.882137 0.446519 0.060 Uiso 1 1 calc R U . . .
C7 C 0.6528(2) 0.0909(2) 0.15977(10) 0.0569(4) Uani 1 1 d . . . . .
H7 H 0.632441 0.047999 0.207209 0.068 Uiso 1 1 calc R U . . .
C4 C 0.6999(2) -0.0055(2) 0.09700(11) 0.0619(4) Uani 1 1 d . . . . .
H4 H 0.712439 -0.110998 0.101729 0.074 Uiso 1 1 calc R U . . .
C5 C 0.6670(2) 0.3127(2) 0.08370(10) 0.0560(4) Uani 1 1 d . . . . .
C21 C -0.2369(2) 0.0336(2) 0.72958(10) 0.0610(4) Uani 1 1 d . . . . .
H21A H -0.310420 -0.008238 0.680907 0.073 Uiso 1 1 calc R U . . .
H21B H -0.309926 0.026203 0.774055 0.073 Uiso 1 1 calc R U . . .
C3 C 0.7288(2) 0.0583(2) 0.02580(10) 0.0615(4) Uani 1 1 d . . . . .
C2 C 0.7124(3) 0.2161(2) 0.02029(10) 0.0681(5) Uani 1 1 d . . . . .
H2A H 0.732708 0.257713 -0.027450 0.082 Uiso 1 1 calc R U . . .
C22 C -0.1183(3) -0.0768(3) 0.73578(13) 0.0790(6) Uani 1 1 d . . . . .
H22A H -0.046527 -0.071498 0.691562 0.119 Uiso 1 1 calc R U . . .
H22B H -0.185227 -0.190319 0.734994 0.119 Uiso 1 1 calc R U . . .
H22C H -0.047754 -0.038716 0.784743 0.119 Uiso 1 1 calc R U . . .
C23 C -0.0771(4) 0.3043(3) 0.80936(15) 0.0544(8) Uani 0.765(6) 1 d D . P A 1
H23A H 0.042987 0.362956 0.807114 0.065 Uiso 0.765(6) 1 calc R U P A 1
H23B H -0.084697 0.227497 0.847561 0.065 Uiso 0.765(6) 1 calc R U P A 1
C1 C 0.7935(3) -0.1882(3) -0.03985(15) 0.0929(7) Uani 1 1 d . . . . .
H1A H 0.881343 -0.183336 0.000232 0.139 Uiso 1 1 calc R U . . .
H1B H 0.825357 -0.231122 -0.091036 0.139 Uiso 1 1 calc R U . . .
H1C H 0.686738 -0.260562 -0.027954 0.139 Uiso 1 1 calc R U . . .
C24 C -0.1770(4) 0.4285(4) 0.8358(2) 0.0809(10) Uani 0.765(6) 1 d D . P A 1
H24A H -0.168589 0.504835 0.798104 0.121 Uiso 0.765(6) 1 calc R U P A 1
H24B H -0.130722 0.489905 0.887318 0.121 Uiso 0.765(6) 1 calc R U P A 1
H24C H -0.295416 0.369968 0.838859 0.121 Uiso 0.765(6) 1 calc R U P A 1
C23A C -0.1768(10) 0.3395(12) 0.7967(5) 0.053(3) Uani 0.235(6) 1 d D . P A 2
H23C H -0.176128 0.443145 0.777373 0.064 Uiso 0.235(6) 1 calc R U P A 2
H23D H -0.285250 0.297982 0.819817 0.064 Uiso 0.235(6) 1 calc R U P A 2
C24A C -0.0264(11) 0.3649(14) 0.8566(6) 0.081(4) Uani 0.235(6) 1 d D . P A 2
H24D H 0.079225 0.402180 0.831677 0.122 Uiso 0.235(6) 1 calc R U P A 2
H24E H -0.030502 0.261012 0.874991 0.122 Uiso 0.235(6) 1 calc R U P A 2
H24F H -0.032756 0.447713 0.900940 0.122 Uiso 0.235(6) 1 calc R U P A 2


_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
S C9 1.7241(16) . ?
S C10 1.7022(16) . ?
O4 C16 1.3757(15) . ?
O4 C13 1.3812(16) . ?
O3 C13 1.2069(17) . ?
N3 C9 1.397(2) . ?
N3 C8 1.288(2) . ?
N2 C11 1.3827(19) . ?
N2 C9 1.2992(17) . ?
O2 H2 0.8200 . ?
O2 C5 1.349(2) . ?
C15 C16 1.3912(19) . ?
C15 C14 1.4157(18) . ?
C15 C17 1.4031(18) . ?
N1 C20 1.3689(18) . ?
N1 C21 1.456(2) . ?
N1 C23 1.486(3) . ?
N1 C23A 1.535(9) . ?
C12 C14 1.3561(18) . ?
C12 C13 1.452(2) . ?
C12 C11 1.4666(19) . ?
C16 C19 1.3720(19) . ?
O1 C3 1.357(2) . ?
O1 C1 1.421(3) . ?
C14 H14 0.9300 . ?
C19 H19 0.9300 . ?
C19 C20 1.4068(19) . ?
C17 H17 0.9300 . ?
C17 C18 1.3659(19) . ?
C11 C10 1.3621(19) . ?
C20 C18 1.414(2) . ?
C6 C8 1.427(2) . ?
C6 C7 1.393(2) . ?
C6 C5 1.412(2) . ?
C18 H18 0.9300 . ?
C8 H8 0.9300 . ?
C10 H10 0.9300 . ?
C7 H7 0.9300 . ?
C7 C4 1.368(2) . ?
C4 H4 0.9300 . ?
C4 C3 1.393(2) . ?
C5 C2 1.370(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.509(3) . ?
C3 C2 1.378(3) . ?
C2 H2A 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.505(4) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C23A H23C 0.9700 . ?
C23A H23D 0.9700 . ?
C23A C24A 1.515(11) . ?
C24A H24D 0.9600 . ?
C24A H24E 0.9600 . ?
C24A H24F 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
C10 S C9 88.96(7) . . ?
C16 O4 C13 122.92(10) . . ?
C8 N3 C9 117.74(12) . . ?
C9 N2 C11 110.22(12) . . ?
C5 O2 H2 109.5 . . ?
C16 C15 C14 118.11(12) . . ?
C16 C15 C17 116.09(12) . . ?
C17 C15 C14 125.80(12) . . ?
C20 N1 C21 121.47(13) . . ?
C20 N1 C23 119.11(14) . . ?
C20 N1 C23A 118.6(3) . . ?
C21 N1 C23 114.43(14) . . ?
C21 N1 C23A 118.0(3) . . ?
C14 C12 C13 119.18(12) . . ?
C14 C12 C11 121.51(13) . . ?
C13 C12 C11 119.31(12) . . ?
O4 C16 C15 119.92(11) . . ?
C19 C16 O4 116.74(12) . . ?
C19 C16 C15 123.33(12) . . ?
C3 O1 C1 118.90(16) . . ?
C15 C14 H14 118.8 . . ?
C12 C14 C15 122.40(12) . . ?
C12 C14 H14 118.8 . . ?
O4 C13 C12 117.22(11) . . ?
O3 C13 O4 115.27(13) . . ?
O3 C13 C12 127.50(13) . . ?
C16 C19 H19 120.1 . . ?
C16 C19 C20 119.86(13) . . ?
C20 C19 H19 120.1 . . ?
C15 C17 H17 119.0 . . ?
C18 C17 C15 122.02(13) . . ?
C18 C17 H17 119.0 . . ?
N2 C11 C12 117.61(12) . . ?
C10 C11 N2 114.69(13) . . ?
C10 C11 C12 127.67(14) . . ?
N1 C20 C19 121.18(13) . . ?
N1 C20 C18 121.53(13) . . ?
C19 C20 C18 117.29(12) . . ?
C7 C6 C8 120.59(13) . . ?
C7 C6 C5 117.09(15) . . ?
C5 C6 C8 122.31(15) . . ?
C17 C18 C20 120.98(12) . . ?
C17 C18 H18 119.5 . . ?
C20 C18 H18 119.5 . . ?
N3 C9 S 118.49(10) . . ?
N2 C9 S 115.36(12) . . ?
N2 C9 N3 126.13(14) . . ?
N3 C8 C6 122.78(13) . . ?
N3 C8 H8 118.6 . . ?
C6 C8 H8 118.6 . . ?
S C10 H10 124.6 . . ?
C11 C10 S 110.75(12) . . ?
C11 C10 H10 124.6 . . ?
C6 C7 H7 118.4 . . ?
C4 C7 C6 123.28(15) . . ?
C4 C7 H7 118.4 . . ?
C7 C4 H4 120.9 . . ?
C7 C4 C3 118.25(17) . . ?
C3 C4 H4 120.9 . . ?
O2 C5 C6 120.99(15) . . ?
O2 C5 C2 119.08(14) . . ?
C2 C5 C6 119.93(16) . . ?
N1 C21 H21A 108.9 . . ?
N1 C21 H21B 108.9 . . ?
N1 C21 C22 113.57(15) . . ?
H21A C21 H21B 107.7 . . ?
C22 C21 H21A 108.9 . . ?
C22 C21 H21B 108.9 . . ?
O1 C3 C4 124.19(18) . . ?
O1 C3 C2 115.73(16) . . ?
C2 C3 C4 120.07(16) . . ?
C5 C2 C3 121.36(15) . . ?
C5 C2 H2A 119.3 . . ?
C3 C2 H2A 119.3 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N1 C23 H23A 109.6 . . ?
N1 C23 H23B 109.6 . . ?
N1 C23 C24 110.1(3) . . ?
H23A C23 H23B 108.2 . . ?
C24 C23 H23A 109.6 . . ?
C24 C23 H23B 109.6 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N1 C23A H23C 111.1 . . ?
N1 C23A H23D 111.1 . . ?
H23C C23A H23D 109.1 . . ?
C24A C23A N1 103.3(8) . . ?
C24A C23A H23C 111.1 . . ?
C24A C23A H23D 111.1 . . ?
C23A C24A H24D 109.5 . . ?
C23A C24A H24E 109.5 . . ?
C23A C24A H24F 109.5 . . ?
H24D C24A H24E 109.5 . . ?
H24D C24A H24F 109.5 . . ?
H24E C24A H24F 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 N3 0.82 1.90 2.6311(17) 147.3 . yes

_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_nnnn_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1975396'
loop_
_audit_author_name
_audit_author_address
'Kerem Kaya'
;Istanbul Technical University, Chemistry Department
Turkey
;
_audit_update_record             
;
2020-10-01 deposited with the CCDC.	2020-11-04 downloaded from the CCDC.
;
_audit_creation_date             2020-09-18
_audit_creation_method           
;
Olex2 1.3-dev
(compiled 2020.09.11 svn.rc89507dd for OlexSys, GUI svn.r5830)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H30 N4 O3 S'
_chemical_formula_sum            'C27 H30 N4 O3 S'
_chemical_formula_weight         490.61
_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      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                   7.6487(14)
_cell_length_b                   8.7524(14)
_cell_length_c                   20.607(3)
_cell_angle_alpha                94.791(7)
_cell_angle_beta                 100.141(7)
_cell_angle_gamma                109.862(7)
_cell_volume                     1261.8(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    24
_cell_measurement_temperature    301(2)
_cell_measurement_theta_max      26
_cell_measurement_theta_min      5
_shelx_estimated_absorpt_T_max   0.989
_shelx_estimated_absorpt_T_min   0.894
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.291
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod_like
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.7
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_unetI/netI     0.0206
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            32175
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.992
_diffrn_reflns_theta_max         24.992
_diffrn_reflns_theta_min         2.504
_diffrn_ambient_temperature      311.4
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  Bruker_D8_VENTRE
_diffrn_measurement_method       ?
_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                3516
_reflns_number_total             4441
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 1.3-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     397
_refine_ls_number_reflns         4441
_refine_ls_number_restraints     134
_refine_ls_R_factor_all          0.0617
_refine_ls_R_factor_gt           0.0463
_refine_ls_restrained_S_all      1.043
_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)+(0.0685P)²+0.5870P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1256
_refine_ls_wR_factor_ref         0.1364
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C23-C19 \\sim C23A-C19A
 with sigma of 0.04
 N4-C25 \\sim N4A-C25
 with sigma of 0.04
 C17-C18 \\sim C17-C18A
 with sigma of 0.02
 C17-C19 \\sim C17-C19A
 with sigma of 0.04
 C21-N4 \\sim C21A-N4A
 with sigma of 0.04
 C18-C19 \\sim C18A-C19A
 with sigma of 0.02
 C21-C23 \\sim C21A-C23A
 with sigma of 0.02
 N4-C23 \\sim N4A-C23A
 with sigma of 0.02
 N4-C26 \\sim N4A-C26A
 with sigma of 0.02
 C23-C22 \\sim C23A-C22A
 with sigma of 0.02
 C18-C21 \\sim C18A-C21A
 with sigma of 0.04
 C19-C22 \\sim C19A-C22A
 with sigma of 0.02
 C18-C22 \\sim C18A-C22A
 with sigma of 0.04
 C21-C22 \\sim C21A-C22A
 with sigma of 0.04
 N4-C22 \\sim N4A-C22A
 with sigma of 0.04
 N4-C27 \\sim N4A-C27A
 with sigma of 0.04
 C26-C27 \\sim C26A-C27A
 with sigma of 0.02
 C23-C26 \\sim C23A-C26A
 with sigma of 0.04
3. Rigid body (RIGU) restrains
 O3, C22, C19, C18, C27, C21, C24, C20, C26, N4, C23
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C22A, C19A, C18A, C27A, C21A, C26A, N4A, C23A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Fixed Sof: H17(0.5) H17A(0.5) C18(0.5) C21(0.5) H21(0.5) N4(0.5) C23(0.5)
 C19(0.5) H19(0.5) C22(0.5) H22(0.5) C26(0.5) H26A(0.5) H26B(0.5) C27(0.5)
 H27A(0.5) H27B(0.5) H27C(0.5) C18A(0.5) C21A(0.5) H21A(0.5) N4A(0.5) C23A(0.5)
 C19A(0.5) H19A(0.5) C22A(0.5) H22A(0.5) C26A(0.5) H26C(0.5) H26D(0.5)
 C27A(0.5) H27D(0.5) H27E(0.5) H27F(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C2(H2A,H2B), C24(H24A,H24B), C26(H26A,H26B), C26A(H26C,H26D)
5.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C9(H9), C6(H6), C7(H7), C17(H17), C17(H17A), C21(H21), C19(H19),
 C22(H22), C15(H15), C21A(H21A), C19A(H19A), C22A(H22A)
5.c Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C1(H1A,H1B,H1C), C25(H25A,H25B,H25C), C27(H27A,H27B,H27C),
 C27A(H27D,H27E,H27F)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 1.05633(9) 0.81838(8) 0.69433(3) 0.0550(2) Uani 1 1 d . . . . .
O1 O 0.64932(19) 0.35520(16) 0.43412(6) 0.0358(3) Uani 1 1 d . . . . .
O2 O 0.8753(2) 0.59562(18) 0.47475(8) 0.0491(4) Uani 1 1 d . . . . .
N2 N 0.7302(2) 0.58225(19) 0.66600(8) 0.0351(4) Uani 1 1 d . . . . .
N1 N 0.1642(2) -0.1564(2) 0.33011(8) 0.0402(4) Uani 1 1 d . . . . .
N3 N 0.8178(3) 0.7307(2) 0.77768(8) 0.0438(4) Uani 1 1 d . . . . .
O3 O 0.9267(2) 0.8587(3) 0.90295(9) 0.0745(6) Uani 1 1 d . . . . .
C10 C 0.4392(3) 0.2053(2) 0.49974(9) 0.0305(4) Uani 1 1 d . . . . .
C12 C 0.6941(3) 0.4633(2) 0.55093(9) 0.0298(4) Uani 1 1 d . . . . .
C11 C 0.5430(3) 0.3304(2) 0.55493(9) 0.0319(4) Uani 1 1 d . . . . .
H11 H 0.505984 0.320786 0.595495 0.038 Uiso 1 1 calc R U . . .
C8 C 0.4970(3) 0.2200(2) 0.43943(9) 0.0303(4) Uani 1 1 d . . . . .
C5 C 0.2541(3) -0.0378(2) 0.38484(9) 0.0325(4) Uani 1 1 d . . . . .
C14 C 0.8037(3) 0.5893(2) 0.60925(10) 0.0338(4) Uani 1 1 d . . . . .
C9 C 0.2824(3) 0.0641(2) 0.50063(10) 0.0349(5) Uani 1 1 d . . . . .
H9 H 0.239017 0.050207 0.539941 0.042 Uiso 1 1 calc R U . . .
C6 C 0.4105(3) 0.1038(2) 0.38326(9) 0.0340(4) Uani 1 1 d . . . . .
H6 H 0.455240 0.118684 0.344237 0.041 Uiso 1 1 calc R U . . .
C7 C 0.1920(3) -0.0530(2) 0.44611(10) 0.0349(5) Uani 1 1 d . . . . .
H7 H 0.088053 -0.144380 0.448761 0.042 Uiso 1 1 calc R U . . .
C16 C 0.8473(3) 0.6963(2) 0.71400(10) 0.0375(5) Uani 1 1 d . . . . .
C13 C 0.7505(3) 0.4816(2) 0.48726(10) 0.0352(5) Uani 1 1 d . . . . .
C3 C 0.0088(3) -0.3078(2) 0.33267(11) 0.0413(5) Uani 1 1 d . . . . .
H3A H 0.033222 -0.340552 0.376162 0.050 Uiso 1 1 calc R U . . .
H3B H 0.006463 -0.394310 0.299498 0.050 Uiso 1 1 calc R U . . .
C17 C 0.6464(3) 0.6739(3) 0.78731(11) 0.0460(5) Uani 1 1 d D . . . .
H17 H 0.544410 0.623123 0.751198 0.055 Uiso 0.5 1 calc R U P A 1
H17A H 0.552300 0.601317 0.752635 0.055 Uiso 0.5 1 calc R U P B 2
C18 C 0.6128(19) 0.689(2) 0.8538(5) 0.037(3) Uani 0.5 1 d D . P C 1
C2 C 0.2178(3) -0.1367(3) 0.26617(10) 0.0489(6) Uani 1 1 d . . . . .
H2A H 0.250268 -0.022301 0.260232 0.059 Uiso 1 1 calc R U . . .
H2B H 0.109537 -0.201807 0.230743 0.059 Uiso 1 1 calc R U . . .
C21 C 0.709(2) 0.811(3) 0.9693(9) 0.051(4) Uani 0.5 1 d D . P C 1
H21 H 0.808198 0.869535 1.005315 0.061 Uiso 0.5 1 calc R U P C 1
C20 C 0.7432(3) 0.7943(3) 0.90711(11) 0.0479(5) Uani 1 1 d . . . . .
N4 N 0.4800(11) 0.7620(10) 1.0395(4) 0.061(2) Uani 0.5 1 d D . P C 1
C4 C -0.1835(3) -0.2907(3) 0.32030(13) 0.0579(7) Uani 1 1 d . . . . .
H4A H -0.180761 -0.202255 0.351801 0.087 Uiso 1 1 calc R U . . .
H4B H -0.278530 -0.391267 0.325409 0.087 Uiso 1 1 calc R U . . .
H4C H -0.213645 -0.267786 0.275813 0.087 Uiso 1 1 calc R U . . .
C23 C 0.5239(16) 0.7413(18) 0.9791(5) 0.047(3) Uani 0.5 1 d D . P C 1
C19 C 0.4269(16) 0.6208(16) 0.8634(6) 0.048(3) Uani 0.5 1 d D . P C 1
H19 H 0.330704 0.557218 0.827288 0.058 Uiso 0.5 1 calc R U P C 1
C1 C 0.3839(4) -0.1880(4) 0.26034(14) 0.0712(8) Uani 1 1 d . . . . .
H1A H 0.491038 -0.125293 0.295739 0.107 Uiso 1 1 calc R U . . .
H1B H 0.416765 -0.168638 0.218116 0.107 Uiso 1 1 calc R U . . .
H1C H 0.350021 -0.302890 0.263446 0.107 Uiso 1 1 calc R U . . .
C24 C 0.6109(4) 0.9029(4) 1.09196(13) 0.0709(8) Uani 1 1 d . . . C 1
H24A H 0.691397 0.989919 1.072434 0.085 Uiso 1 1 calc R U . C 1
H24B H 0.540290 0.947478 1.117965 0.085 Uiso 1 1 calc R U . C 1
C22 C 0.3811(16) 0.6433(17) 0.9231(5) 0.055(3) Uani 0.5 1 d D . P C 1
H22 H 0.255967 0.594512 0.927391 0.066 Uiso 0.5 1 calc R U P C 1
C25 C 0.7226(6) 0.8241(5) 1.13257(17) 0.0978(11) Uani 1 1 d . . . C 1
H25A H 0.797103 0.787662 1.106353 0.147 Uiso 1 1 calc R U . C 1
H25B H 0.638146 0.731465 1.147327 0.147 Uiso 1 1 calc R U . C 1
H25C H 0.805677 0.901622 1.170623 0.147 Uiso 1 1 calc R U . C 1
C15 C 0.9779(3) 0.7109(2) 0.61491(10) 0.0322(4) Uani 1 1 d . . . . .
H15 H 1.043581 0.731799 0.580758 0.039 Uiso 1 1 calc R U . . .
C26 C 0.3047(8) 0.6550(9) 1.0555(3) 0.0593(12) Uani 0.5 1 d D . P C 1
H26A H 0.334766 0.629619 1.100106 0.071 Uiso 0.5 1 calc R U P C 1
H26B H 0.255389 0.552460 1.024717 0.071 Uiso 0.5 1 calc R U P C 1
C27 C 0.1508(9) 0.7284(9) 1.0522(4) 0.0806(18) Uani 0.5 1 d D . P C 1
H27A H 0.111500 0.744495 1.007224 0.121 Uiso 0.5 1 calc R U P C 1
H27B H 0.199707 0.832114 1.081189 0.121 Uiso 0.5 1 calc R U P C 1
H27C H 0.043624 0.654925 1.066052 0.121 Uiso 0.5 1 calc R U P C 1
C18A C 0.5904(18) 0.714(2) 0.8472(5) 0.035(3) Uani 0.5 1 d D . P C 2
C21A C 0.688(2) 0.830(3) 0.9658(8) 0.045(3) Uani 0.5 1 d D . P C 2
H21A H 0.781838 0.895786 1.002216 0.054 Uiso 0.5 1 calc R U P C 2
N4A N 0.4551(10) 0.8140(9) 1.0317(4) 0.0558(18) Uani 0.5 1 d D . P C 2
C23A C 0.4986(17) 0.7732(19) 0.9727(5) 0.046(2) Uani 0.5 1 d D . P C 2
C19A C 0.4035(16) 0.6579(16) 0.8564(6) 0.047(2) Uani 0.5 1 d D . P C 2
H19A H 0.305864 0.600385 0.819746 0.056 Uiso 0.5 1 calc R U P C 2
C22A C 0.3565(18) 0.6824(17) 0.9156(5) 0.055(3) Uani 0.5 1 d D . P C 2
H22A H 0.229844 0.639246 0.918889 0.066 Uiso 0.5 1 calc R U P C 2
C26A C 0.2621(10) 0.7579(9) 1.0427(3) 0.0717(16) Uani 0.5 1 d D . P C 2
H26C H 0.174068 0.748391 1.001184 0.086 Uiso 0.5 1 calc R U P C 2
H26D H 0.251069 0.839750 1.074894 0.086 Uiso 0.5 1 calc R U P C 2
C27A C 0.2066(13) 0.5965(9) 1.0675(4) 0.108(3) Uani 0.5 1 d D . P C 2
H27D H 0.211862 0.513754 1.035090 0.162 Uiso 0.5 1 calc R U P C 2
H27E H 0.079321 0.566874 1.074679 0.162 Uiso 0.5 1 calc R U P C 2
H27F H 0.292786 0.605000 1.108783 0.162 Uiso 0.5 1 calc R U P C 2
H3 H 0.934(4) 0.816(4) 0.8496(16) 0.092(10) Uiso 1 1 d . . . . .


_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 C16 1.732(2) . ?
S1 C15 1.7138(19) . ?
O1 C8 1.378(2) . ?
O1 C13 1.393(2) . ?
O2 C13 1.206(2) . ?
N2 C14 1.381(2) . ?
N2 C16 1.301(3) . ?
N1 C5 1.367(2) . ?
N1 C3 1.461(3) . ?
N1 C2 1.454(3) . ?
N3 C16 1.396(3) . ?
N3 C17 1.292(3) . ?
O3 C20 1.345(3) . ?
O3 H3 1.15(3) . ?
C10 C11 1.416(3) . ?
C10 C8 1.392(3) . ?
C10 C9 1.404(3) . ?
C12 C11 1.354(3) . ?
C12 C14 1.469(3) . ?
C12 C13 1.456(3) . ?
C11 H11 0.9300 . ?
C8 C6 1.374(3) . ?
C5 C6 1.408(3) . ?
C5 C7 1.426(3) . ?
C14 C15 1.372(3) . ?
C9 H9 0.9300 . ?
C9 C7 1.358(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.508(3) . ?
C17 H17 0.9300 . ?
C17 H17A 0.9300 . ?
C17 C18 1.441(9) . ?
C17 C18A 1.430(9) . ?
C18 C20 1.368(13) . ?
C18 C19 1.401(9) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C2 C1 1.504(4) . ?
C21 H21 0.9300 . ?
C21 C20 1.360(14) . ?
C21 C23 1.395(9) . ?
C20 C18A 1.474(12) . ?
C20 C21A 1.396(12) . ?
N4 C23 1.359(8) . ?
N4 C24 1.499(9) . ?
N4 C26 1.462(8) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C23 C22 1.420(8) . ?
C19 H19 0.9300 . ?
C19 C22 1.353(8) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C24 H24A 0.9700 . ?
C24 H24B 0.9700 . ?
C24 C25 1.467(5) . ?
C22 H22 0.9300 . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C15 H15 0.9300 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 C27 1.515(8) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C18A C19A 1.398(8) . ?
C21A H21A 0.9300 . ?
C21A C23A 1.401(9) . ?
N4A C23A 1.367(8) . ?
N4A C26A 1.454(8) . ?
C23A C22A 1.415(9) . ?
C19A H19A 0.9300 . ?
C19A C22A 1.351(8) . ?
C22A H22A 0.9300 . ?
C26A H26C 0.9700 . ?
C26A H26D 0.9700 . ?
C26A C27A 1.492(9) . ?
C27A H27D 0.9600 . ?
C27A H27E 0.9600 . ?
C27A H27F 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
C15 S1 C16 89.22(9) . . ?
C8 O1 C13 122.61(14) . . ?
C16 N2 C14 110.26(17) . . ?
C5 N1 C3 121.87(16) . . ?
C5 N1 C2 121.34(17) . . ?
C2 N1 C3 116.78(17) . . ?
C17 N3 C16 118.60(18) . . ?
C20 O3 H3 106.9(16) . . ?
C8 C10 C11 118.28(17) . . ?
C8 C10 C9 116.29(17) . . ?
C9 C10 C11 125.41(17) . . ?
C11 C12 C14 121.76(17) . . ?
C11 C12 C13 119.20(17) . . ?
C13 C12 C14 119.04(17) . . ?
C10 C11 H11 118.7 . . ?
C12 C11 C10 122.55(17) . . ?
C12 C11 H11 118.7 . . ?
O1 C8 C10 120.08(17) . . ?
C6 C8 O1 116.65(16) . . ?
C6 C8 C10 123.27(18) . . ?
N1 C5 C6 121.77(17) . . ?
N1 C5 C7 120.96(17) . . ?
C6 C5 C7 117.27(17) . . ?
N2 C14 C12 117.57(17) . . ?
C15 C14 N2 115.41(18) . . ?
C15 C14 C12 126.95(17) . . ?
C10 C9 H9 118.8 . . ?
C7 C9 C10 122.30(18) . . ?
C7 C9 H9 118.8 . . ?
C8 C6 C5 119.93(17) . . ?
C8 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C5 C7 H7 119.5 . . ?
C9 C7 C5 120.92(18) . . ?
C9 C7 H7 119.5 . . ?
N2 C16 S1 115.25(15) . . ?
N2 C16 N3 126.45(19) . . ?
N3 C16 S1 118.28(15) . . ?
O1 C13 C12 117.21(16) . . ?
O2 C13 O1 115.48(17) . . ?
O2 C13 C12 127.30(19) . . ?
N1 C3 H3A 108.9 . . ?
N1 C3 H3B 108.9 . . ?
N1 C3 C4 113.15(18) . . ?
H3A C3 H3B 107.8 . . ?
C4 C3 H3A 108.9 . . ?
C4 C3 H3B 108.9 . . ?
N3 C17 H17 119.9 . . ?
N3 C17 H17A 117.5 . . ?
N3 C17 C18 120.3(6) . . ?
N3 C17 C18A 125.1(6) . . ?
C18 C17 H17 119.9 . . ?
C18A C17 H17A 117.5 . . ?
C20 C18 C17 123.9(10) . . ?
C20 C18 C19 115.4(8) . . ?
C19 C18 C17 119.4(10) . . ?
N1 C2 H2A 109.0 . . ?
N1 C2 H2B 109.0 . . ?
N1 C2 C1 112.7(2) . . ?
H2A C2 H2B 107.8 . . ?
C1 C2 H2A 109.0 . . ?
C1 C2 H2B 109.0 . . ?
C20 C21 H21 120.0 . . ?
C20 C21 C23 120.1(11) . . ?
C23 C21 H21 120.0 . . ?
O3 C20 C18 119.0(5) . . ?
O3 C20 C21 115.9(7) . . ?
O3 C20 C18A 121.3(4) . . ?
O3 C20 C21A 120.3(6) . . ?
C21 C20 C18 123.6(9) . . ?
C21A C20 C18A 117.1(8) . . ?
C23 N4 C24 119.7(7) . . ?
C23 N4 C26 122.7(8) . . ?
C26 N4 C24 117.6(6) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C21 C23 C22 117.1(8) . . ?
N4 C23 C21 122.4(9) . . ?
N4 C23 C22 120.5(8) . . ?
C18 C19 H19 118.6 . . ?
C22 C19 C18 122.8(10) . . ?
C22 C19 H19 118.6 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
N4 C24 H24A 111.4 . . ?
N4 C24 H24B 111.4 . . ?
H24A C24 H24B 109.3 . . ?
C25 C24 N4 101.8(4) . . ?
C25 C24 H24A 111.4 . . ?
C25 C24 H24B 111.4 . . ?
C23 C22 H22 119.9 . . ?
C19 C22 C23 120.1(9) . . ?
C19 C22 H22 119.9 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25B 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
S1 C15 H15 125.1 . . ?
C14 C15 S1 109.84(14) . . ?
C14 C15 H15 125.1 . . ?
N4 C26 H26A 108.8 . . ?
N4 C26 H26B 108.8 . . ?
N4 C26 C27 114.0(7) . . ?
H26A C26 H26B 107.6 . . ?
C27 C26 H26A 108.8 . . ?
C27 C26 H26B 108.8 . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C17 C18A C20 117.2(8) . . ?
C19A C18A C17 124.9(9) . . ?
C19A C18A C20 116.9(7) . . ?
C20 C21A H21A 118.3 . . ?
C20 C21A C23A 123.3(10) . . ?
C23A C21A H21A 118.3 . . ?
C23A N4A C26A 123.1(8) . . ?
C21A C23A C22A 117.5(8) . . ?
N4A C23A C21A 120.1(9) . . ?
N4A C23A C22A 122.2(9) . . ?
C18A C19A H19A 118.1 . . ?
C22A C19A C18A 123.8(10) . . ?
C22A C19A H19A 118.1 . . ?
C23A C22A H22A 119.7 . . ?
C19A C22A C23A 120.6(9) . . ?
C19A C22A H22A 119.7 . . ?
N4A C26A H26C 108.9 . . ?
N4A C26A H26D 108.9 . . ?
N4A C26A C27A 113.2(8) . . ?
H26C C26A H26D 107.8 . . ?
C27A C26A H26C 108.9 . . ?
C27A C26A H26D 108.9 . . ?
C26A C27A H27D 109.5 . . ?
C26A C27A H27E 109.5 . . ?
C26A C27A H27F 109.5 . . ?
H27D C27A H27E 109.5 . . ?
H27D C27A H27F 109.5 . . ?
H27E C27A H27F 109.5 . . ?

_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_NNsal_01m_a
_database_code_depnum_ccdc_archive 'CCDC 1975398'
loop_
_audit_author_name
_audit_author_address
'Kerem Kaya'
;Istanbul Technical University, Chemistry Department
Turkey
;
_audit_update_record             
;
2020-10-01 deposited with the CCDC.	2020-11-04 downloaded from the CCDC.
;
_audit_creation_date             2020-08-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         'C23 H21 N3 O3 S'
_chemical_formula_sum            'C23 H21 N3 O3 S'
_chemical_formula_weight         419.51
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
S 0.12424 0.12443 6.90530 5.20340 1.43790 1.58630 1.46790 22.21510 0.25360
56.17200 0.866900026798
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   8.4790(7)
_cell_length_b                   10.8451(8)
_cell_length_c                   12.1470(10)
_cell_angle_alpha                75.707(4)
_cell_angle_beta                 89.516(4)
_cell_angle_gamma                72.029(3)
_cell_volume                     1026.82(14)
_cell_measurement_reflns_used    24
_cell_measurement_theta_min      5
_cell_measurement_theta_max      25
_exptl_transmission_factor_min   0.825
_exptl_transmission_factor_max   0.955
_cell_formula_units_Z            2
_cell_measurement_temperature    304(2)
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_type   Multi_Scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            dark_orange
_exptl_crystal_density_diffrn    1.3567
_exptl_crystal_description       rod
_exptl_crystal_F_000             440.4416
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_diffrn_reflns_av_R_equivalents  0.0932
_diffrn_reflns_av_unetI/netI     0.0448
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            47651
_diffrn_reflns_theta_full        28.3749
_diffrn_reflns_theta_max         28.37
_diffrn_reflns_theta_min         2.32
_diffrn_ambient_temperature      303.8
_diffrn_measured_fraction_theta_full 0.9977
_diffrn_measured_fraction_theta_max 0.9977
_diffrn_measurement_device_type  Bruker_D8_Venture
_diffrn_measurement_method       'ω and phi scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -11
_reflns_limit_k_max              14
_reflns_limit_k_min              -13
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                3331
_reflns_number_total             5146
_reflns_threshold_expression     I>=2u(I)
_computing_data_collection       'Bruker APEX2'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_refine_diff_density_max         0.3920
_refine_diff_density_min         -0.3231
_refine_diff_density_rms         0.0763
_refine_ls_d_res_high            0.7478
_refine_ls_d_res_low             8.7949
_refine_ls_goodness_of_fit_ref   1.0181
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    36
_refine_ls_number_parameters     274
_refine_ls_number_reflns         5146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0851
_refine_ls_R_factor_gt           0.0457
_refine_ls_restrained_S_all      1.0181
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0570P)²+0.1070P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1043
_refine_ls_wR_factor_ref         0.1190
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2(H2a,H2b), C3(H3a,H3b)
2.b Aromatic/amide H refined with riding coordinates:
 C11(H11), C8(H8), C6(H6), C7(H7), C17(H17), C15(H15), C19(H19), C22(H22),
 C20(H20), C21(H21)
2.c Idealised Me refined as rotating group:
 C1(H1a,H1b,H1c), C4(H4a,H4b,H4c)
2.d Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
S S 0.84392(5) 0.12823(4) 0.54689(4) 0.05105(15) Uani 1.000000 .
O2 O 0.41683(12) 0.54729(9) 0.76802(9) 0.0414(3) Uani 1.000000 .
O1 O 1.12686(16) 0.13933(12) 0.22433(11) 0.0590(3) Uani 1.000000 .
H1 H 1.072(2) 0.1481(6) 0.2796(11) 0.0886(5) Uiso 1.000000 GR
O3 O 0.47780(16) 0.33651(11) 0.76852(11) 0.0605(3) Uani 1.000000 .
N1 N 0.96405(15) 0.26483(12) 0.37030(11) 0.0414(3) Uani 1.000000 .
N2 N 0.79106(14) 0.38175(12) 0.49450(10) 0.0380(3) Uani 1.000000 .
N3 N 0.28370(17) 0.99111(13) 0.80856(12) 0.0497(4) Uani 1.000000 .
C10 C 0.53926(17) 0.69605(14) 0.64459(12) 0.0354(3) Uani 1.000000 .
C13 C 0.61355(17) 0.46378(14) 0.63695(12) 0.0352(3) Uani 1.000000 .
C9 C 0.43505(17) 0.67234(14) 0.73119(12) 0.0351(3) Uani 1.000000 .
C14 C 0.70659(17) 0.35236(14) 0.59003(12) 0.0363(3) Uani 1.000000 .
C11 C 0.62626(18) 0.58843(14) 0.59861(12) 0.0375(3) Uani 1.000000 .
H11 H 0.69459(18) 0.60383(14) 0.53998(12) 0.0450(4) Uiso 1.000000 R
C12 C 0.50345(19) 0.44031(15) 0.72634(13) 0.0393(4) Uani 1.000000 .
C8 C 0.55169(19) 0.82581(15) 0.61375(13) 0.0412(4) Uani 1.000000 .
H8 H 0.61942(19) 0.84676(15) 0.55623(13) 0.0494(4) Uiso 1.000000 R
C5 C 0.36349(18) 0.89601(15) 0.75393(13) 0.0398(4) Uani 1.000000 .
C18 C 1.08047(18) 0.37325(16) 0.21016(13) 0.0421(4) Uani 1.000000 .
C6 C 0.46765(19) 0.92196(15) 0.66545(13) 0.0429(4) Uani 1.000000 .
H6 H 0.47889(19) 1.00701(15) 0.64207(13) 0.0515(4) Uiso 1.000000 R
C16 C 0.86745(18) 0.27353(15) 0.46332(13) 0.0389(4) Uani 1.000000 .
C7 C 0.34774(18) 0.76708(15) 0.78447(13) 0.0401(4) Uani 1.000000 .
H7 H 0.27823(18) 0.74608(15) 0.84070(13) 0.0482(4) Uiso 1.000000 R
C17 C 0.98591(19) 0.37214(16) 0.30880(13) 0.0441(4) Uani 1.000000 .
H17 H 0.93862(19) 0.45232(16) 0.32893(13) 0.0530(5) Uiso 1.000000 R
C23 C 1.14889(19) 0.25734(18) 0.17179(14) 0.0469(4) Uani 1.000000 .
C15 C 0.7223(2) 0.21990(15) 0.62929(14) 0.0457(4) Uani 1.000000 .
H15 H 0.6730(2) 0.18425(15) 0.69273(14) 0.0548(5) Uiso 1.000000 R
C2 C 0.3041(2) 1.12300(16) 0.78063(15) 0.0528(4) Uani 1.000000 .
H2a H 0.2881(2) 1.15775(16) 0.84763(15) 0.0634(5) Uiso 1.000000 R
H2b H 0.4170(2) 1.11478(16) 0.76001(15) 0.0634(5) Uiso 1.000000 R
C3 C 0.1809(2) 0.96284(17) 0.90174(16) 0.0548(5) Uani 1.000000 .
H3a H 0.1025(2) 1.04666(17) 0.90895(16) 0.0657(5) Uiso 1.000000 R
H3b H 0.1175(2) 0.90877(17) 0.88369(16) 0.0657(5) Uiso 1.000000 R
C19 C 1.1092(2) 0.49088(18) 0.15145(16) 0.0586(5) Uani 1.000000 .
H19 H 1.0644(2) 0.56856(18) 0.17578(16) 0.0703(6) Uiso 1.000000 R
C22 C 1.2427(2) 0.2626(2) 0.07789(16) 0.0629(5) Uani 1.000000 .
H22 H 1.2885(2) 0.1858(2) 0.05261(16) 0.0755(6) Uiso 1.000000 R
C20 C 1.2020(2) 0.4948(2) 0.05855(17) 0.0695(6) Uani 1.000000 .
H20 H 1.2200(2) 0.5743(2) 0.02042(17) 0.0833(7) Uiso 1.000000 R
C21 C 1.2687(2) 0.3801(2) 0.02194(17) 0.0725(6) Uani 1.000000 .
H21 H 1.3316(2) 0.3824(2) -0.04116(17) 0.0870(7) Uiso 1.000000 R
C1 C 0.1844(3) 1.22187(18) 0.68392(19) 0.0729(6) Uani 1.000000 .
H1a H 0.2008(12) 1.1889(7) 0.6169(4) 0.1094(9) Uiso 1.000000 GR
H1b H 0.0723(3) 1.2327(11) 0.7046(5) 0.1094(9) Uiso 1.000000 GR
H1c H 0.2041(12) 1.3068(4) 0.6689(8) 0.1094(9) Uiso 1.000000 GR
C4 C 0.2803(3) 0.8902(2) 1.01434(17) 0.0768(6) Uani 1.000000 .
H4a H 0.3536(13) 0.8047(7) 1.0092(4) 0.1152(9) Uiso 1.000000 GR
H4b H 0.3444(14) 0.9426(7) 1.0324(6) 0.1152(9) Uiso 1.000000 GR
H4c H 0.2061(3) 0.8770(13) 1.0730(3) 0.1152(9) Uiso 1.000000 GR


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
S C16 1.7188(16) . ?
S C15 1.7015(16) . ?
O2 C9 1.3754(16) . ?
O2 C12 1.3783(17) . ?
O1 H1 0.8200 . ?
O1 C23 1.350(2) . ?
O3 C12 1.2005(17) . ?
N1 C16 1.3949(19) . ?
N1 C17 1.2838(19) . ?
N2 C14 1.3804(19) . ?
N2 C16 1.2987(18) . ?
N3 C5 1.3645(19) . ?
N3 C2 1.450(2) . ?
N3 C3 1.453(2) . ?
C10 C9 1.394(2) . ?
C10 C11 1.415(2) . ?
C10 C8 1.401(2) . ?
C13 C14 1.467(2) . ?
C13 C11 1.3543(19) . ?
C13 C12 1.452(2) . ?
C9 C7 1.369(2) . ?
C14 C15 1.362(2) . ?
C11 H11 0.9300 . ?
C8 H8 0.9300 . ?
C8 C6 1.359(2) . ?
C5 C6 1.415(2) . ?
C5 C7 1.403(2) . ?
C18 C17 1.436(2) . ?
C18 C23 1.403(2) . ?
C18 C19 1.391(2) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C17 H17 0.9300 . ?
C23 C22 1.385(2) . ?
C15 H15 0.9300 . ?
C2 H2a 0.9700 . ?
C2 H2b 0.9700 . ?
C2 C1 1.512(3) . ?
C3 H3a 0.9700 . ?
C3 H3b 0.9700 . ?
C3 C4 1.510(3) . ?
C19 H19 0.9300 . ?
C19 C20 1.370(3) . ?
C22 H22 0.9300 . ?
C22 C21 1.369(3) . ?
C20 H20 0.9300 . ?
C20 C21 1.378(3) . ?
C21 H21 0.9300 . ?
C1 H1a 0.9600 . ?
C1 H1b 0.9600 . ?
C1 H1c 0.9600 . ?
C4 H4a 0.9600 . ?
C4 H4b 0.9600 . ?
C4 H4c 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
C15 S C16 88.92(7) . . ?
C12 O2 C9 122.78(11) . . ?
C23 O1 H1 109.5 . . ?
C17 N1 C16 118.73(13) . . ?
C16 N2 C14 110.63(12) . . ?
C2 N3 C5 121.71(13) . . ?
C3 N3 C5 121.56(13) . . ?
C3 N3 C2 116.65(13) . . ?
C11 C10 C9 118.33(13) . . ?
C8 C10 C9 115.74(13) . . ?
C8 C10 C11 125.90(13) . . ?
C11 C13 C14 121.88(13) . . ?
C12 C13 C14 119.17(12) . . ?
C12 C13 C11 118.95(13) . . ?
C10 C9 O2 119.78(12) . . ?
C7 C9 O2 116.35(12) . . ?
C7 C9 C10 123.87(13) . . ?
C13 C14 N2 117.73(12) . . ?
C15 C14 N2 114.18(13) . . ?
C15 C14 C13 128.10(14) . . ?
C13 C11 C10 122.34(13) . . ?
H11 C11 C10 118.83(8) . . ?
H11 C11 C13 118.83(8) . . ?
O3 C12 O2 115.32(13) . . ?
C13 C12 O2 117.75(12) . . ?
C13 C12 O3 126.92(14) . . ?
H8 C8 C10 119.04(8) . . ?
C6 C8 C10 121.91(14) . . ?
C6 C8 H8 119.04(9) . . ?
C6 C5 N3 121.70(14) . . ?
C7 C5 N3 121.27(14) . . ?
C7 C5 C6 117.03(13) . . ?
C23 C18 C17 121.78(15) . . ?
C19 C18 C17 119.88(15) . . ?
C19 C18 C23 118.32(15) . . ?
C5 C6 C8 121.69(14) . . ?
H6 C6 C8 119.15(9) . . ?
H6 C6 C5 119.15(9) . . ?
N1 C16 S 118.11(11) . . ?
N2 C16 S 115.26(11) . . ?
N2 C16 N1 126.64(14) . . ?
C5 C7 C9 119.75(14) . . ?
H7 C7 C9 120.13(8) . . ?
H7 C7 C5 120.13(9) . . ?
C18 C17 N1 122.60(14) . . ?
H17 C17 N1 118.70(9) . . ?
H17 C17 C18 118.70(9) . . ?
C18 C23 O1 121.85(14) . . ?
C22 C23 O1 118.50(16) . . ?
C22 C23 C18 119.65(17) . . ?
C14 C15 S 111.02(12) . . ?
H15 C15 S 124.49(5) . . ?
H15 C15 C14 124.49(9) . . ?
H2a C2 N3 108.95(9) . . ?
H2b C2 N3 108.95(9) . . ?
H2b C2 H2a 107.8 . . ?
C1 C2 N3 113.15(15) . . ?
C1 C2 H2a 108.95(10) . . ?
C1 C2 H2b 108.95(11) . . ?
H3a C3 N3 108.96(8) . . ?
H3b C3 N3 108.96(9) . . ?
H3b C3 H3a 107.8 . . ?
C4 C3 N3 113.10(15) . . ?
C4 C3 H3a 108.96(10) . . ?
C4 C3 H3b 108.96(11) . . ?
H19 C19 C18 119.29(10) . . ?
C20 C19 C18 121.43(18) . . ?
C20 C19 H19 119.29(13) . . ?
H22 C22 C23 119.71(12) . . ?
C21 C22 C23 120.58(18) . . ?
C21 C22 H22 119.71(12) . . ?
H20 C20 C19 120.20(13) . . ?
C21 C20 C19 119.60(19) . . ?
C21 C20 H20 120.20(12) . . ?
C20 C21 C22 120.42(18) . . ?
H21 C21 C22 119.79(12) . . ?
H21 C21 C20 119.79(12) . . ?
H1a C1 C2 109.5 . . ?
H1b C1 C2 109.5 . . ?
H1b C1 H1a 109.5 . . ?
H1c C1 C2 109.5 . . ?
H1c C1 H1a 109.5 . . ?
H1c C1 H1b 109.5 . . ?
H4a C4 C3 109.5 . . ?
H4b C4 C3 109.5 . . ?
H4b C4 H4a 109.5 . . ?
H4c C4 C3 109.5 . . ?
H4c C4 H4a 109.5 . . ?
H4c C4 H4b 109.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
