# 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 2015

####################################################################### 
# 
# 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_mo_fs401_0m
_database_code_depnum_ccdc_archive 'CCDC 1045374'
_audit_update_record             
;
2015-01-25 deposited with the CCDC.
2015-08-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H18 N4 O3 S, C2 H6 O S'
_chemical_formula_sum            'C24 H24 N4 O4 S2'
_chemical_formula_weight         496.59

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   23.177(5)
_cell_length_b                   8.5606(17)
_cell_length_c                   23.924(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4746.9(17)
_cell_formula_units_Z            8
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    1313
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      20.05
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.390
_exptl_crystal_F_000             2080
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.211
_exptl_crystal_size_min          0.075
_exptl_absorpt_coefficient_mu    0.263
_shelx_estimated_absorpt_T_min   0.911
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.911
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'

_exptl_special_details           
; 
?
;

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  
;
Bruker SMART APEX II DUO CCD area-detector diffractometer 
;
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20862
_diffrn_reflns_av_unetI/netI     0.0961
_diffrn_reflns_av_R_equivalents  0.1065
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.702
_diffrn_reflns_theta_max         26.528
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4898
_reflns_number_gt                2126
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and PLATON (Spek, 2009)'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0954P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4898
_refine_ls_number_parameters     310
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1569
_refine_ls_R_factor_gt           0.0623
_refine_ls_wR_factor_ref         0.2121
_refine_ls_wR_factor_gt          0.1553
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_restrained_S_all      0.962
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001

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 0.08485(5) 0.44213(15) 0.24142(5) 0.0719(4) Uani 1 1 d . . . . .
O1 O 0.17039(11) 0.2851(3) 0.29379(11) 0.0602(8) Uani 1 1 d . . . . .
H1O1 H 0.1844 0.2210 0.3152 0.090 Uiso 1 1 d R U . . .
O2 O 0.16849(13) -0.0119(4) 0.41903(13) 0.0736(9) Uani 1 1 d . . . . .
O3 O 0.41522(15) -0.0970(4) 0.51104(16) 0.1022(12) Uani 1 1 d . . . . .
H1O3 H 0.4077 -0.0371 0.4850 0.153 Uiso 1 1 d R U . . .
N1 N 0.13677(15) 0.5643(4) 0.15670(14) 0.0596(9) Uani 1 1 d . . . . .
N2 N 0.24519(15) 0.1405(4) 0.35425(13) 0.0524(8) Uani 1 1 d . . . . .
N3 N 0.26122(15) 0.0422(4) 0.39705(14) 0.0568(9) Uani 1 1 d . . . . .
H1N3 H 0.2948 0.0382 0.4115 0.068 Uiso 1 1 d R U . . .
N4 N 0.30020(15) -0.1366(4) 0.47810(13) 0.0551(9) Uani 1 1 d . . . . .
C1 C 0.0436(2) 0.5410(5) 0.19293(19) 0.0657(12) Uani 1 1 d . . . . .
C2 C -0.0156(2) 0.5666(7) 0.1917(2) 0.0942(17) Uani 1 1 d . . . . .
H2A H -0.0392 0.5287 0.2201 0.113 Uiso 1 1 calc R U . . .
C3 C -0.0384(3) 0.6492(8) 0.1478(3) 0.1022(19) Uani 1 1 d . . . . .
H3A H -0.0780 0.6666 0.1463 0.123 Uiso 1 1 calc R U . . .
C4 C -0.0039(3) 0.7059(7) 0.1064(3) 0.1011(19) Uani 1 1 d . . . . .
H4A H -0.0205 0.7620 0.0772 0.121 Uiso 1 1 calc R U . . .
C5 C 0.0557(2) 0.6820(6) 0.1066(2) 0.0811(15) Uani 1 1 d . . . . .
H5A H 0.0790 0.7219 0.0783 0.097 Uiso 1 1 calc R U . . .
C6 C 0.07882(19) 0.5976(5) 0.14996(19) 0.0603(12) Uani 1 1 d . . . . .
C7 C 0.14626(17) 0.4845(4) 0.20218(17) 0.0525(10) Uani 1 1 d . . . . .
C8 C 0.20485(17) 0.4391(4) 0.21896(16) 0.0471(9) Uani 1 1 d . . . . .
C9 C 0.25155(18) 0.4981(4) 0.18960(17) 0.0531(10) Uani 1 1 d . . . . .
H9A H 0.2443 0.5635 0.1593 0.064 Uiso 1 1 calc R U . . .
C10 C 0.30805(18) 0.4652(4) 0.20281(17) 0.0522(10) Uani 1 1 d . . . . .
C11 C 0.31760(18) 0.3665(4) 0.24744(17) 0.0535(10) Uani 1 1 d . . . . .
H11A H 0.3554 0.3413 0.2567 0.064 Uiso 1 1 calc R U . . .
C12 C 0.27315(17) 0.3029(4) 0.27915(16) 0.0461(9) Uani 1 1 d . . . . .
C13 C 0.21612(18) 0.3410(4) 0.26453(16) 0.0486(10) Uani 1 1 d . . . . .
C14 C 0.28599(19) 0.1993(4) 0.32474(17) 0.0527(10) Uani 1 1 d . . . . .
H14A H 0.3242 0.1747 0.3329 0.063 Uiso 1 1 calc R U . . .
C15 C 0.2197(2) -0.0269(5) 0.42822(18) 0.0551(11) Uani 1 1 d . . . . .
C16 C 0.24298(19) -0.1248(4) 0.47462(16) 0.0506(10) Uani 1 1 d . . . . .
C17 C 0.2060(2) -0.1964(5) 0.51095(19) 0.0657(12) Uani 1 1 d . . . . .
H17A H 0.1663 -0.1855 0.5068 0.079 Uiso 1 1 calc R U . . .
C18 C 0.2286(2) -0.2855(5) 0.55413(19) 0.0721(13) Uani 1 1 d . . . . .
H18A H 0.2045 -0.3346 0.5798 0.087 Uiso 1 1 calc R U . . .
C19 C 0.2871(2) -0.2988(5) 0.55773(18) 0.0651(12) Uani 1 1 d . . . . .
H19A H 0.3037 -0.3586 0.5859 0.078 Uiso 1 1 calc R U . . .
C20 C 0.32183(19) -0.2225(5) 0.51895(17) 0.0556(11) Uani 1 1 d . . . . .
C21 C 0.3861(2) -0.2374(6) 0.5198(2) 0.0860(16) Uani 1 1 d . . . . .
H21A H 0.3977 -0.2799 0.5556 0.103 Uiso 1 1 calc R U . . .
H21B H 0.3976 -0.3111 0.4911 0.103 Uiso 1 1 calc R U . . .
C22 C 0.35804(19) 0.5341(5) 0.17101(18) 0.0683(12) Uani 1 1 d . . . . .
H22A H 0.3464 0.5552 0.1332 0.102 Uiso 1 1 calc R U . . .
H22B H 0.3896 0.4615 0.1709 0.102 Uiso 1 1 calc R U . . .
H22C H 0.3700 0.6296 0.1886 0.102 Uiso 1 1 calc R U . . .
S2 S 0.43052(5) 0.20639(15) 0.38964(5) 0.0743(4) Uani 1 1 d . . . . .
O4 O 0.39329(14) 0.0822(4) 0.41363(15) 0.0900(10) Uani 1 1 d . . . . .
C24 C 0.4577(2) 0.3140(5) 0.4461(2) 0.0890(16) Uani 1 1 d . . . . .
H24A H 0.4269 0.3717 0.4633 0.134 Uiso 1 1 calc R U . . .
H24B H 0.4866 0.3853 0.4330 0.134 Uiso 1 1 calc R U . . .
H24C H 0.4744 0.2441 0.4730 0.134 Uiso 1 1 calc R U . . .
C23 C 0.4967(2) 0.1150(6) 0.3702(2) 0.0989(17) Uani 1 1 d . . . . .
H23A H 0.4894 0.0385 0.3417 0.148 Uiso 1 1 calc R U . . .
H23B H 0.5133 0.0649 0.4023 0.148 Uiso 1 1 calc R U . . .
H23C H 0.5229 0.1924 0.3562 0.148 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C1 1.725(5) . ?
S1 C7 1.743(4) . ?
O1 C13 1.358(5) . ?
O1 H1O1 0.8173 . ?
O2 C15 1.215(5) . ?
O3 C21 1.394(6) . ?
O3 H1O3 0.8250 . ?
N1 C7 1.303(5) . ?
N1 C6 1.383(5) . ?
N2 C14 1.283(5) . ?
N2 N3 1.377(4) . ?
N3 C15 1.353(5) . ?
N3 H1N3 0.8535 . ?
N4 C20 1.322(5) . ?
N4 C16 1.333(5) . ?
C1 C2 1.390(6) . ?
C1 C6 1.399(6) . ?
C2 C3 1.372(7) . ?
C2 H2A 0.9300 . ?
C3 C4 1.363(8) . ?
C3 H3A 0.9300 . ?
C4 C5 1.397(7) . ?
C4 H4A 0.9300 . ?
C5 C6 1.372(6) . ?
C5 H5A 0.9300 . ?
C7 C8 1.468(5) . ?
C8 C9 1.386(5) . ?
C8 C13 1.401(5) . ?
C9 C10 1.376(5) . ?
C9 H9A 0.9300 . ?
C10 C11 1.380(5) . ?
C10 C22 1.506(5) . ?
C11 C12 1.390(5) . ?
C11 H11A 0.9300 . ?
C12 C13 1.406(5) . ?
C12 C14 1.437(5) . ?
C14 H14A 0.9300 . ?
C15 C16 1.491(6) . ?
C16 C17 1.366(6) . ?
C17 C18 1.386(6) . ?
C17 H17A 0.9300 . ?
C18 C19 1.364(6) . ?
C18 H18A 0.9300 . ?
C19 C20 1.392(6) . ?
C19 H19A 0.9300 . ?
C20 C21 1.495(6) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
S2 O4 1.485(3) . ?
S2 C24 1.752(5) . ?
S2 C23 1.783(5) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 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
C1 S1 C7 89.3(2) . . ?
C13 O1 H1O1 104.4 . . ?
C21 O3 H1O3 123.1 . . ?
C7 N1 C6 111.7(4) . . ?
C14 N2 N3 116.8(4) . . ?
C15 N3 N2 119.0(4) . . ?
C15 N3 H1N3 114.0 . . ?
N2 N3 H1N3 125.0 . . ?
C20 N4 C16 117.8(4) . . ?
C2 C1 C6 120.4(5) . . ?
C2 C1 S1 129.7(4) . . ?
C6 C1 S1 109.9(3) . . ?
C3 C2 C1 118.5(5) . . ?
C3 C2 H2A 120.7 . . ?
C1 C2 H2A 120.7 . . ?
C4 C3 C2 120.9(5) . . ?
C4 C3 H3A 119.5 . . ?
C2 C3 H3A 119.5 . . ?
C3 C4 C5 121.7(5) . . ?
C3 C4 H4A 119.2 . . ?
C5 C4 H4A 119.2 . . ?
C6 C5 C4 117.8(5) . . ?
C6 C5 H5A 121.1 . . ?
C4 C5 H5A 121.1 . . ?
C5 C6 N1 125.2(5) . . ?
C5 C6 C1 120.7(4) . . ?
N1 C6 C1 114.2(4) . . ?
N1 C7 C8 121.5(4) . . ?
N1 C7 S1 114.9(3) . . ?
C8 C7 S1 123.6(3) . . ?
C9 C8 C13 117.9(4) . . ?
C9 C8 C7 119.2(4) . . ?
C13 C8 C7 122.9(4) . . ?
C10 C9 C8 123.5(4) . . ?
C10 C9 H9A 118.2 . . ?
C8 C9 H9A 118.2 . . ?
C9 C10 C11 117.1(4) . . ?
C9 C10 C22 122.4(4) . . ?
C11 C10 C22 120.5(4) . . ?
C10 C11 C12 122.9(4) . . ?
C10 C11 H11A 118.6 . . ?
C12 C11 H11A 118.6 . . ?
C11 C12 C13 118.1(4) . . ?
C11 C12 C14 120.1(4) . . ?
C13 C12 C14 121.8(4) . . ?
O1 C13 C8 117.9(4) . . ?
O1 C13 C12 121.6(3) . . ?
C8 C13 C12 120.5(4) . . ?
N2 C14 C12 120.5(4) . . ?
N2 C14 H14A 119.8 . . ?
C12 C14 H14A 119.8 . . ?
O2 C15 N3 123.3(4) . . ?
O2 C15 C16 123.2(4) . . ?
N3 C15 C16 113.5(4) . . ?
N4 C16 C17 123.4(4) . . ?
N4 C16 C15 116.7(4) . . ?
C17 C16 C15 119.9(4) . . ?
C16 C17 C18 119.0(4) . . ?
C16 C17 H17A 120.5 . . ?
C18 C17 H17A 120.5 . . ?
C19 C18 C17 117.9(4) . . ?
C19 C18 H18A 121.0 . . ?
C17 C18 H18A 121.0 . . ?
C18 C19 C20 119.6(4) . . ?
C18 C19 H19A 120.2 . . ?
C20 C19 H19A 120.2 . . ?
N4 C20 C19 122.3(4) . . ?
N4 C20 C21 115.8(4) . . ?
C19 C20 C21 121.9(4) . . ?
O3 C21 C20 114.0(4) . . ?
O3 C21 H21A 108.7 . . ?
C20 C21 H21A 108.7 . . ?
O3 C21 H21B 108.7 . . ?
C20 C21 H21B 108.7 . . ?
H21A C21 H21B 107.6 . . ?
C10 C22 H22A 109.5 . . ?
C10 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C10 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O4 S2 C24 106.7(2) . . ?
O4 S2 C23 106.6(2) . . ?
C24 S2 C23 97.1(2) . . ?
S2 C24 H24A 109.5 . . ?
S2 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
S2 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
S2 C23 H23A 109.5 . . ?
S2 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
S2 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C14 N2 N3 C15 -177.8(3) . . . . ?
C7 S1 C1 C2 -179.9(5) . . . . ?
C7 S1 C1 C6 0.8(3) . . . . ?
C6 C1 C2 C3 -0.4(7) . . . . ?
S1 C1 C2 C3 -179.6(4) . . . . ?
C1 C2 C3 C4 -0.5(9) . . . . ?
C2 C3 C4 C5 0.4(9) . . . . ?
C3 C4 C5 C6 0.6(8) . . . . ?
C4 C5 C6 N1 -179.5(4) . . . . ?
C4 C5 C6 C1 -1.4(7) . . . . ?
C7 N1 C6 C5 178.9(4) . . . . ?
C7 N1 C6 C1 0.6(5) . . . . ?
C2 C1 C6 C5 1.3(7) . . . . ?
S1 C1 C6 C5 -179.3(4) . . . . ?
C2 C1 C6 N1 179.7(4) . . . . ?
S1 C1 C6 N1 -1.0(5) . . . . ?
C6 N1 C7 C8 -178.3(3) . . . . ?
C6 N1 C7 S1 0.0(4) . . . . ?
C1 S1 C7 N1 -0.5(3) . . . . ?
C1 S1 C7 C8 177.8(3) . . . . ?
N1 C7 C8 C9 7.9(6) . . . . ?
S1 C7 C8 C9 -170.3(3) . . . . ?
N1 C7 C8 C13 -173.7(3) . . . . ?
S1 C7 C8 C13 8.1(5) . . . . ?
C13 C8 C9 C10 0.1(6) . . . . ?
C7 C8 C9 C10 178.6(4) . . . . ?
C8 C9 C10 C11 0.8(6) . . . . ?
C8 C9 C10 C22 -178.5(4) . . . . ?
C9 C10 C11 C12 -1.0(6) . . . . ?
C22 C10 C11 C12 178.3(4) . . . . ?
C10 C11 C12 C13 0.4(5) . . . . ?
C10 C11 C12 C14 179.3(3) . . . . ?
C9 C8 C13 O1 179.1(3) . . . . ?
C7 C8 C13 O1 0.6(5) . . . . ?
C9 C8 C13 C12 -0.8(5) . . . . ?
C7 C8 C13 C12 -179.2(3) . . . . ?
C11 C12 C13 O1 -179.3(3) . . . . ?
C14 C12 C13 O1 1.9(5) . . . . ?
C11 C12 C13 C8 0.5(5) . . . . ?
C14 C12 C13 C8 -178.3(3) . . . . ?
N3 N2 C14 C12 179.9(3) . . . . ?
C11 C12 C14 N2 179.8(3) . . . . ?
C13 C12 C14 N2 -1.3(5) . . . . ?
N2 N3 C15 O2 3.1(6) . . . . ?
N2 N3 C15 C16 -177.5(3) . . . . ?
C20 N4 C16 C17 0.0(6) . . . . ?
C20 N4 C16 C15 179.9(3) . . . . ?
O2 C15 C16 N4 176.9(4) . . . . ?
N3 C15 C16 N4 -2.6(5) . . . . ?
O2 C15 C16 C17 -3.3(6) . . . . ?
N3 C15 C16 C17 177.3(4) . . . . ?
N4 C16 C17 C18 0.5(6) . . . . ?
C15 C16 C17 C18 -179.3(4) . . . . ?
C16 C17 C18 C19 -0.8(6) . . . . ?
C17 C18 C19 C20 0.7(7) . . . . ?
C16 N4 C20 C19 -0.2(6) . . . . ?
C16 N4 C20 C21 177.7(4) . . . . ?
C18 C19 C20 N4 -0.2(6) . . . . ?
C18 C19 C20 C21 -177.9(4) . . . . ?
N4 C20 C21 O3 44.8(6) . . . . ?
C19 C20 C21 O3 -137.3(4) . . . . ?

_refine_diff_density_max         0.275
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.061

_shelxl_version_number           2014-3

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
O1 H1O1 N2 0.8200 1.8300 2.575(4) 152.00 . yes
O3 H1O3 O4 0.8300 2.0200 2.836(5) 171.00 . yes
N3 H1N3 O4 0.8500 2.3100 3.106(5) 155.00 . yes
C14 H14A S2 0.9300 2.8300 3.693(5) 155.00 . yes

