# 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 2018

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1552443'
_audit_update_record             
;
2017-05-25 deposited with the CCDC.
2018-03-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C37 H25 N5 O2, C2 H6 O S'
_chemical_formula_sum            'C39 H31 N5 O3 S'
_chemical_formula_weight         649.75

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_IT_number  14
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'


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

_cell_length_a                   10.0344(4)
_cell_length_b                   8.1177(3)
_cell_length_c                   20.1951(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.782(2)
_cell_angle_gamma                90.00
_cell_volume                     1629.87(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    17720
_cell_measurement_theta_min      2.408
_cell_measurement_theta_max      28.314

_exptl_crystal_description       squre
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680.0
_exptl_absorpt_coefficient_mu    0.147
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.971
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_process_details   '(SADAB; Bruker, 2000)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17690
_diffrn_reflns_av_R_equivalents  0.0593
_diffrn_reflns_av_sigmaI/netI    0.2026
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.41
_diffrn_reflns_theta_max         28.31
_reflns_number_total             8133
_reflns_number_gt                2584
_reflns_threshold_expression     'I > 2sigma(I)'

_computing_data_collection       'Bruker Kappa Apex'
_computing_cell_refinement       'Bruker Kappa Apex'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0603P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.89(17)
_refine_ls_number_reflns         8133
_refine_ls_number_parameters     449
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1766
_refine_ls_R_factor_gt           0.0603
_refine_ls_wR_factor_ref         0.1592
_refine_ls_wR_factor_gt          0.1319
_refine_ls_goodness_of_fit_ref   0.794
_refine_ls_restrained_S_all      0.793
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C12 C 0.0535(5) -0.2954(6) 0.8247(2) 0.0465(12) Uani 1 1 d . . .
C10 C 0.0140(4) -0.1196(5) 0.7247(2) 0.0393(10) Uani 1 1 d . . .
C11 C 0.1066(4) -0.1921(5) 0.7774(2) 0.0353(10) Uani 1 1 d . . .
N1 N 0.3110(3) -0.4769(4) 0.63671(16) 0.0359(8) Uani 1 1 d . . .
C20 C -0.2190(5) -0.0740(6) 0.6703(2) 0.0531(13) Uani 1 1 d . . .
H20 H -0.1892 -0.0071 0.6379 0.064 Uiso 1 1 calc R . .
C17 C -0.0840(5) -0.3219(5) 0.8196(2) 0.0465(12) Uani 1 1 d . . .
H17 H -0.1174 -0.3873 0.8514 0.056 Uiso 1 1 calc R . .
C19 C -0.1232(4) -0.1467(5) 0.7213(2) 0.0412(11) Uani 1 1 d . . .
C18 C -0.1723(4) -0.2546(5) 0.7691(2) 0.0441(11) Uani 1 1 d . . .
C4 C 0.3191(4) -0.3879(5) 0.5814(2) 0.0345(10) Uani 1 1 d . . .
C7 C 0.2790(4) -0.2112(5) 0.5833(2) 0.0409(10) Uani 1 1 d . . .
N5 N 0.1943(4) -0.1792(5) 0.62971(18) 0.0418(9) Uani 1 1 d . . .
C1 C 0.3983(5) -0.6177(6) 0.5245(2) 0.0529(12) Uani 1 1 d . . .
H1 H 0.4253 -0.6660 0.4867 0.063 Uiso 1 1 calc R . .
C5 C 0.3511(4) -0.6343(5) 0.6351(2) 0.0371(10) Uani 1 1 d . . .
C3 C 0.3916(4) -0.7089(6) 0.5806(2) 0.0517(12) Uani 1 1 d . . .
H3 H 0.4143 -0.8200 0.5817 0.062 Uiso 1 1 calc R . .
C6 C 0.3445(4) -0.7337(5) 0.6988(2) 0.0386(10) Uani 1 1 d . . .
N2 N 0.2545(4) -0.6809(5) 0.73623(19) 0.0428(10) Uani 1 1 d . . .
C2 C 0.3641(5) -0.4510(6) 0.5242(2) 0.0518(13) Uani 1 1 d . . .
H2 H 0.3711 -0.3846 0.4873 0.062 Uiso 1 1 calc R . .
O1 O 0.3154(3) -0.1111(4) 0.54517(15) 0.0579(9) Uani 1 1 d . . .
O2 O 0.4202(3) -0.8506(4) 0.71218(16) 0.0581(9) Uani 1 1 d . . .
C16 C 0.1424(5) -0.3641(6) 0.8781(2) 0.0536(13) Uani 1 1 d . . .
H16 H 0.1080 -0.4289 0.9098 0.064 Uiso 1 1 calc R . .
C15 C 0.2789(5) -0.3364(6) 0.8839(2) 0.0563(13) Uani 1 1 d . . .
H15 H 0.3367 -0.3841 0.9185 0.068 Uiso 1 1 calc R . .
C13 C 0.2483(4) -0.1625(5) 0.7867(2) 0.0441(11) Uani 1 1 d . . .
H13 H 0.2851 -0.0920 0.7577 0.053 Uiso 1 1 calc R . .
C14 C 0.3292(5) -0.2353(6) 0.8370(2) 0.0559(13) Uani 1 1 d . . .
H14 H 0.4214 -0.2178 0.8406 0.067 Uiso 1 1 calc R . .
C23 C -0.3161(5) -0.2792(7) 0.7633(3) 0.0641(15) Uani 1 1 d . . .
H23 H -0.3508 -0.3467 0.7940 0.077 Uiso 1 1 calc R . .
C22 C -0.4008(5) -0.2073(8) 0.7148(3) 0.0718(16) Uani 1 1 d . . .
H22 H -0.4926 -0.2281 0.7120 0.086 Uiso 1 1 calc R . .
C21 C -0.3542(6) -0.1026(8) 0.6690(3) 0.0741(16) Uani 1 1 d . . .
H21 H -0.4153 -0.0510 0.6368 0.089 Uiso 1 1 calc R . .
N4 N 0.1429(4) -0.0244(4) 0.63319(17) 0.0475(10) Uani 1 1 d . . .
C8 C 0.1208(5) -0.7328(5) 0.8144(2) 0.0398(10) Uani 1 1 d . . .
N3 N 0.2295(4) -0.7683(4) 0.79121(16) 0.0403(9) Uani 1 1 d . . .
C9 C 0.0635(5) 0.0000(6) 0.6771(2) 0.0483(12) Uani 1 1 d . . .
C24 C 0.0804(4) -0.8257(5) 0.87085(19) 0.0372(10) Uani 1 1 d . . .
C33 C -0.0587(4) -0.8616(5) 0.8694(2) 0.0431(11) Uani 1 1 d . . .
C25 C 0.1770(5) -0.8829(5) 0.9249(2) 0.0398(11) Uani 1 1 d . . .
C34 C -0.1598(5) -0.8015(6) 0.8193(3) 0.0637(15) Uani 1 1 d . . .
H34 H -0.1352 -0.7353 0.7853 0.076 Uiso 1 1 calc R . .
C26 C 0.3141(5) -0.8375(6) 0.9331(2) 0.0553(13) Uani 1 1 d . . .
H26 H 0.3452 -0.7685 0.9018 0.066 Uiso 1 1 calc R . .
C35 C -0.2925(6) -0.8389(9) 0.8199(3) 0.091(2) Uani 1 1 d . . .
H35 H -0.3571 -0.7978 0.7866 0.109 Uiso 1 1 calc R . .
C30 C 0.1297(5) -0.9894(5) 0.9739(2) 0.0483(12) Uani 1 1 d . . .
C32 C -0.0995(5) -0.9673(6) 0.9209(2) 0.0527(13) Uani 1 1 d . . .
C28 C 0.3570(7) -0.9990(7) 1.0329(3) 0.0738(16) Uani 1 1 d . . .
H28 H 0.4180 -1.0386 1.0680 0.089 Uiso 1 1 calc R . .
C31 C -0.0025(6) -1.0289(6) 0.9701(2) 0.0585(14) Uani 1 1 d . . .
H31 H -0.0292 -1.1004 1.0018 0.070 Uiso 1 1 calc R . .
C29 C 0.2281(7) -1.0451(6) 1.0282(2) 0.0619(14) Uani 1 1 d . . .
H29 H 0.2012 -1.1144 1.0606 0.074 Uiso 1 1 calc R . .
C37 C -0.2398(7) -1.0040(7) 0.9183(3) 0.0789(18) Uani 1 1 d . . .
H37 H -0.2675 -1.0739 0.9503 0.095 Uiso 1 1 calc R . .
C36 C -0.3322(6) -0.9405(9) 0.8713(4) 0.090(2) Uani 1 1 d . . .
H36 H -0.4229 -0.9629 0.8721 0.108 Uiso 1 1 calc R . .
C27 C 0.4023(6) -0.8926(7) 0.9862(3) 0.0655(15) Uani 1 1 d . . .
H27 H 0.4918 -0.8594 0.9912 0.079 Uiso 1 1 calc R . .
S1 S 0.0832(2) -0.0696(4) 0.39460(10) 0.1230(8) Uani 1 1 d . . .
O3 O -0.0053(5) -0.0388(7) 0.3307(2) 0.1192(19) Uani 1 1 d . . .
C39 C 0.2461(7) -0.0454(10) 0.3816(3) 0.115(3) Uani 1 1 d . . .
H39A H 0.2673 -0.1246 0.3493 0.172 Uiso 1 1 calc R . .
H39B H 0.3042 -0.0619 0.4229 0.172 Uiso 1 1 calc R . .
H39C H 0.2587 0.0638 0.3653 0.172 Uiso 1 1 calc R . .
C38 C 0.0705(11) 0.0700(18) 0.4512(4) 0.213(6) Uani 1 1 d . . .
H38A H -0.0188 0.0686 0.4632 0.319 Uiso 1 1 calc R . .
H38B H 0.0887 0.1765 0.4338 0.319 Uiso 1 1 calc R . .
H38C H 0.1342 0.0473 0.4900 0.319 Uiso 1 1 calc R . .
H41 H 0.197(4) -0.624(5) 0.722(2) 0.029(13) Uiso 1 1 d . . .
H40 H 0.176(3) -0.260(4) 0.6576(16) 0.009(8) Uiso 1 1 d . . .
H8 H 0.051(4) -0.669(5) 0.7879(18) 0.036(11) Uiso 1 1 d . . .
H9 H 0.008(4) 0.123(6) 0.676(2) 0.058(12) 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
C12 C17 1.386(6) . ?
C12 C16 1.418(6) . ?
C12 C11 1.427(6) . ?
C10 C19 1.387(6) . ?
C10 C11 1.441(6) . ?
C10 C9 1.498(6) . ?
C11 C13 1.429(6) . ?
N1 C5 1.341(5) . ?
N1 C4 1.343(5) . ?
C20 C21 1.373(7) . ?
C20 C19 1.437(6) . ?
C17 C18 1.370(6) . ?
C19 C18 1.439(6) . ?
C18 C23 1.446(7) . ?
C4 C2 1.393(6) . ?
C4 C7 1.492(6) . ?
C7 O1 1.209(5) . ?
C7 N5 1.373(5) . ?
N5 N4 1.364(5) . ?
C1 C3 1.363(6) . ?
C1 C2 1.396(7) . ?
C5 C3 1.365(6) . ?
C5 C6 1.529(5) . ?
C6 O2 1.222(5) . ?
C6 N2 1.324(6) . ?
N2 N3 1.369(5) . ?
C16 C15 1.377(7) . ?
C15 C14 1.399(7) . ?
C13 C14 1.348(6) . ?
C23 C22 1.340(7) . ?
C22 C21 1.384(8) . ?
N4 C9 1.284(6) . ?
C8 N3 1.276(5) . ?
C8 C24 1.470(6) . ?
C24 C33 1.422(6) . ?
C24 C25 1.435(6) . ?
C33 C34 1.419(7) . ?
C33 C32 1.449(6) . ?
C25 C26 1.413(6) . ?
C25 C30 1.441(6) . ?
C34 C35 1.368(7) . ?
C26 C27 1.369(6) . ?
C35 C36 1.424(10) . ?
C30 C31 1.357(7) . ?
C30 C29 1.446(7) . ?
C32 C31 1.386(7) . ?
C32 C37 1.434(8) . ?
C28 C29 1.338(8) . ?
C28 C27 1.399(8) . ?
C37 C36 1.338(9) . ?
S1 O3 1.484(4) . ?
S1 C38 1.627(10) . ?
S1 C39 1.702(7) . ?

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
C17 C12 C16 120.9(4) . . ?
C17 C12 C11 120.0(4) . . ?
C16 C12 C11 119.1(4) . . ?
C19 C10 C11 120.5(4) . . ?
C19 C10 C9 119.0(4) . . ?
C11 C10 C9 120.2(4) . . ?
C12 C11 C13 117.8(4) . . ?
C12 C11 C10 118.2(4) . . ?
C13 C11 C10 123.9(4) . . ?
C5 N1 C4 116.1(3) . . ?
C21 C20 C19 120.5(5) . . ?
C18 C17 C12 122.0(4) . . ?
C10 C19 C20 122.2(4) . . ?
C10 C19 C18 119.5(4) . . ?
C20 C19 C18 118.3(4) . . ?
C17 C18 C19 119.7(4) . . ?
C17 C18 C23 122.9(5) . . ?
C19 C18 C23 117.3(5) . . ?
N1 C4 C2 123.7(4) . . ?
N1 C4 C7 116.7(3) . . ?
C2 C4 C7 119.6(4) . . ?
O1 C7 N5 125.2(4) . . ?
O1 C7 C4 121.6(4) . . ?
N5 C7 C4 113.2(4) . . ?
N4 N5 C7 118.9(4) . . ?
C3 C1 C2 119.3(4) . . ?
N1 C5 C3 124.4(4) . . ?
N1 C5 C6 115.8(4) . . ?
C3 C5 C6 119.8(4) . . ?
C1 C3 C5 118.9(4) . . ?
O2 C6 N2 125.3(4) . . ?
O2 C6 C5 119.9(4) . . ?
N2 C6 C5 114.8(4) . . ?
C6 N2 N3 120.6(4) . . ?
C4 C2 C1 117.4(4) . . ?
C15 C16 C12 121.1(4) . . ?
C16 C15 C14 119.0(4) . . ?
C14 C13 C11 120.8(4) . . ?
C13 C14 C15 122.2(5) . . ?
C22 C23 C18 121.8(5) . . ?
C23 C22 C21 121.2(5) . . ?
C20 C21 C22 120.9(5) . . ?
C9 N4 N5 116.8(4) . . ?
N3 C8 C24 120.5(4) . . ?
C8 N3 N2 116.1(4) . . ?
N4 C9 C10 129.3(4) . . ?
C33 C24 C25 120.6(4) . . ?
C33 C24 C8 117.6(4) . . ?
C25 C24 C8 121.8(4) . . ?
C34 C33 C24 123.3(4) . . ?
C34 C33 C32 118.1(4) . . ?
C24 C33 C32 118.6(4) . . ?
C26 C25 C24 123.5(4) . . ?
C26 C25 C30 118.8(4) . . ?
C24 C25 C30 117.7(4) . . ?
C35 C34 C33 121.4(6) . . ?
C27 C26 C25 121.5(5) . . ?
C34 C35 C36 120.2(6) . . ?
C31 C30 C25 120.9(5) . . ?
C31 C30 C29 122.1(5) . . ?
C25 C30 C29 117.0(5) . . ?
C31 C32 C37 122.8(5) . . ?
C31 C32 C33 119.3(4) . . ?
C37 C32 C33 117.9(5) . . ?
C29 C28 C27 121.6(5) . . ?
C30 C31 C32 122.8(5) . . ?
C28 C29 C30 121.4(5) . . ?
C36 C37 C32 121.9(6) . . ?
C37 C36 C35 120.4(6) . . ?
C26 C27 C28 119.7(6) . . ?
O3 S1 C38 113.5(4) . . ?
O3 S1 C39 108.7(3) . . ?
C38 S1 C39 101.3(5) . . ?

_diffrn_measured_fraction_theta_max 0.921
_diffrn_reflns_theta_full        28.31
_diffrn_measured_fraction_theta_full 2.408
_refine_diff_density_max         0.589
_refine_diff_density_min         -0.455
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1577825'
_audit_update_record             
;
2017-10-03 deposited with the CCDC.
2018-03-21 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H21 N5 O4,C2 H6 O S'
_chemical_formula_sum            'C31 H27 N5 O5 S'
_chemical_formula_weight         581.64

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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   30.297(12)
_cell_length_b                   12.301(5)
_cell_length_c                   16.640(7)
_cell_angle_alpha                90
_cell_angle_beta                 112.00(2)
_cell_angle_gamma                90
_cell_volume                     5750(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3666
_cell_measurement_theta_min      0.926
_cell_measurement_theta_max      29.158

_exptl_crystal_description       square
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.344
_exptl_crystal_F_000             2432.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_absorpt_coefficient_mu    0.162
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.926
_exptl_absorpt_correction_T_max  0.926
_exptl_absorpt_process_details   '(SADAB; Bruker, 2000)'

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40920
_diffrn_reflns_av_unetI/netI     0.0495
_diffrn_reflns_av_R_equivalents  0.0678
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.807
_diffrn_reflns_theta_max         29.158
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.926
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7191
_reflns_number_gt                3666
_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       'Bruker Kappa Apex'
_computing_cell_refinement       'Bruker Kappa Apex'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1374P)²+8.5990P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7191
_refine_ls_number_parameters     403
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1561
_refine_ls_R_factor_gt           0.0863
_refine_ls_wR_factor_ref         0.2939
_refine_ls_wR_factor_gt          0.2384
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.91637(6) 0.19742(14) 0.63310(8) 0.1013(6) Uani 1 1 d . . . . .
C18 C 0.89860(14) 0.0504(3) 0.3660(2) 0.0565(9) Uani 1 1 d . . . . .
O5 O 0.89862(9) 0.2629(2) 0.55300(16) 0.0671(7) Uani 1 1 d . . . . .
O1 O 0.71963(10) 0.2614(2) 0.35651(19) 0.0756(8) Uani 1 1 d . . . . .
O2 O 0.72641(11) 0.5271(3) 0.5031(3) 0.0854(10) Uani 1 1 d . . . . .
N5 N 0.82807(10) 0.1359(2) 0.37349(17) 0.0517(7) Uani 1 1 d . . . . .
N1 N 0.79598(14) 0.2996(3) 0.4411(2) 0.0604(9) Uani 1 1 d . . . . .
C2 C 0.81138(12) 0.5482(3) 0.5627(2) 0.0482(8) Uani 1 1 d . . . . .
N2 N 0.78436(11) 0.3922(2) 0.47450(19) 0.0571(8) Uani 1 1 d . . . . .
C17 C 0.84568(14) 0.0530(3) 0.3429(2) 0.0548(9) Uani 1 1 d . . . . .
C7 C 0.85102(12) 0.6158(3) 0.6129(2) 0.0491(8) Uani 1 1 d . . . . .
C13 C 0.78087(13) 0.1435(3) 0.3499(2) 0.0544(9) Uani 1 1 d . . . . .
C1 C 0.81938(14) 0.4487(3) 0.5240(2) 0.0525(8) Uani 1 1 d . . . . .
C6 C 0.84204(15) 0.7154(3) 0.6473(2) 0.0596(10) Uani 1 1 d . . . . .
C12 C 0.76200(14) 0.2389(3) 0.3824(2) 0.0574(9) Uani 1 1 d . . . . .
C3 C 0.76568(14) 0.5826(3) 0.5511(3) 0.0636(10) Uani 1 1 d . . . . .
C8 C 0.89833(13) 0.5908(3) 0.6266(2) 0.0595(9) Uani 1 1 d . . . . .
H8 H 0.9052 0.5259 0.6051 0.071 Uiso 1 1 calc R U . . .
C16 C 0.81629(16) -0.0249(3) 0.2876(2) 0.0664(11) Uani 1 1 d . . . . .
H16 H 0.8292 -0.0822 0.2671 0.080 Uiso 1 1 calc R U . . .
C5 C 0.79495(18) 0.7427(4) 0.6347(3) 0.0788(13) Uani 1 1 d . . . . .
H5 H 0.7890 0.8069 0.6585 0.095 Uiso 1 1 calc R U . . .
C14 C 0.74972(15) 0.0698(3) 0.2945(2) 0.0659(10) Uani 1 1 d . . . . .
H14 H 0.7170 0.0779 0.2784 0.079 Uiso 1 1 calc R U . . .
C10 C 0.9257(2) 0.7589(4) 0.7037(3) 0.0824(14) Uani 1 1 d . . . . .
H10 H 0.9505 0.8059 0.7333 0.099 Uiso 1 1 calc R U . . .
C15 C 0.76783(16) -0.0154(4) 0.2639(3) 0.0736(12) Uani 1 1 d . . . . .
H15 H 0.7475 -0.0666 0.2272 0.088 Uiso 1 1 calc R U . . .
C9 C 0.93484(16) 0.6604(4) 0.6712(3) 0.0772(12) Uani 1 1 d . . . . .
H9 H 0.9660 0.6415 0.6798 0.093 Uiso 1 1 calc R U . . .
C11 C 0.88035(19) 0.7855(3) 0.6917(3) 0.0739(12) Uani 1 1 d . . . . .
H11 H 0.8743 0.8512 0.7132 0.089 Uiso 1 1 calc R U . . .
C4 C 0.75798(17) 0.6782(4) 0.5891(3) 0.0837(14) Uani 1 1 d . . . . .
H4 H 0.7272 0.6975 0.5830 0.100 Uiso 1 1 calc R U . . .
O3 O 0.91790(11) -0.0158(2) 0.33515(18) 0.0723(8) Uani 1 1 d . . . . .
N3 N 0.92157(11) 0.1306(3) 0.4209(2) 0.0575(8) Uani 1 1 d . . . . .
N4 N 0.96978(11) 0.1422(3) 0.44525(19) 0.0581(8) Uani 1 1 d . . . . .
O4 O 1.05436(14) 0.0844(3) 0.4575(2) 0.0742(9) Uani 1 1 d . . . . .
C20 C 1.03886(12) 0.2492(3) 0.5198(2) 0.0493(8) Uani 1 1 d . . . . .
C19 C 0.98836(13) 0.2270(3) 0.4911(2) 0.0537(9) Uani 1 1 d . . . . .
C21 C 1.06937(14) 0.1770(3) 0.5012(2) 0.0570(9) Uani 1 1 d . . . . .
C24 C 1.10736(13) 0.3716(3) 0.5886(2) 0.0566(9) Uani 1 1 d . . . . .
C25 C 1.05802(12) 0.3488(3) 0.5654(2) 0.0511(8) Uani 1 1 d . . . . .
C26 C 1.03108(14) 0.4276(3) 0.5882(2) 0.0628(10) Uani 1 1 d . . . . .
H26 H 0.9990 0.4143 0.5758 0.075 Uiso 1 1 calc R U . . .
C23 C 1.13635(15) 0.2936(4) 0.5702(3) 0.0676(11) Uani 1 1 d . . . . .
H23 H 1.1688 0.3073 0.5872 0.081 Uiso 1 1 calc R U . . .
C22 C 1.11856(15) 0.1993(4) 0.5286(3) 0.0681(11) Uani 1 1 d . . . . .
H22 H 1.1388 0.1492 0.5180 0.082 Uiso 1 1 calc R U . . .
C28 C 1.12589(15) 0.4719(4) 0.6287(2) 0.0684(11) Uani 1 1 d . . . . .
H28 H 1.1579 0.4871 0.6422 0.082 Uiso 1 1 calc R U . . .
C29 C 1.09850(17) 0.5463(4) 0.6480(3) 0.0782(12) Uani 1 1 d . . . . .
H29 H 1.1114 0.6118 0.6741 0.094 Uiso 1 1 calc R U . . .
C30 C 1.05057(17) 0.5228(4) 0.6278(3) 0.0764(12) Uani 1 1 d . . . . .
H30 H 1.0315 0.5728 0.6416 0.092 Uiso 1 1 calc R U . . .
C32 C 0.9008(2) 0.2673(5) 0.7129(3) 0.1082(19) Uani 1 1 d . . . . .
H32A H 0.9119 0.2265 0.7660 0.162 Uiso 1 1 calc R U . . .
H32B H 0.9153 0.3380 0.7229 0.162 Uiso 1 1 calc R U . . .
H32C H 0.8669 0.2749 0.6927 0.162 Uiso 1 1 calc R U . . .
C31 C 0.8819(3) 0.1004(9) 0.6234(4) 0.171(4) Uani 1 1 d . . . . .
H31A H 0.8931 0.0572 0.6752 0.257 Uiso 1 1 calc R U . . .
H31B H 0.8507 0.1275 0.6141 0.257 Uiso 1 1 calc R U . . .
H31C H 0.8806 0.0565 0.5749 0.257 Uiso 1 1 calc R U . . .
H20 H 0.8191(12) 0.278(3) 0.454(2) 0.034(10) Uiso 1 1 d . . . . .
H19 H 0.9642(16) 0.280(4) 0.497(3) 0.084(14) Uiso 1 1 d . . . . .
H1 H 0.8544(16) 0.422(3) 0.541(3) 0.079(13) Uiso 1 1 d . . . . .
H44 H 0.9094(18) 0.173(4) 0.457(3) 0.103(17) Uiso 1 1 d . . . . .
H45 H 0.7332(16) 0.473(4) 0.486(3) 0.071(16) Uiso 1 1 d . . . . .
H46 H 1.0276(17) 0.075(4) 0.445(3) 0.078(18) 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 O5 1.476(3) . ?
S1 C31 1.554(10) . ?
S1 C32 1.787(5) . ?
C18 O3 1.223(4) . ?
C18 N3 1.347(5) . ?
C18 C17 1.502(5) . ?
O1 C12 1.223(5) . ?
O2 C3 1.344(5) . ?
N5 C13 1.337(5) . ?
N5 C17 1.336(5) . ?
N1 C12 1.348(5) . ?
N1 N2 1.371(4) . ?
C2 C3 1.390(5) . ?
C2 C7 1.443(5) . ?
C2 C1 1.444(5) . ?
N2 C1 1.278(5) . ?
C17 C16 1.395(5) . ?
C7 C8 1.399(5) . ?
C7 C6 1.420(5) . ?
C13 C14 1.383(5) . ?
C13 C12 1.492(5) . ?
C6 C5 1.403(6) . ?
C6 C11 1.412(6) . ?
C3 C4 1.395(6) . ?
C8 C9 1.375(6) . ?
C16 C15 1.375(6) . ?
C5 C4 1.351(7) . ?
C14 C15 1.367(6) . ?
C10 C11 1.352(7) . ?
C10 C9 1.397(7) . ?
N3 N4 1.369(4) . ?
N4 C19 1.290(5) . ?
O4 C21 1.336(5) . ?
C20 C21 1.397(5) . ?
C20 C25 1.444(5) . ?
C20 C19 1.448(5) . ?
C21 C22 1.412(6) . ?
C24 C23 1.410(6) . ?
C24 C28 1.414(6) . ?
C24 C25 1.425(5) . ?
C25 C26 1.407(5) . ?
C26 C30 1.365(6) . ?
C23 C22 1.355(6) . ?
C28 C29 1.352(6) . ?
C29 C30 1.393(6) . ?

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
O5 S1 C31 108.8(3) . . ?
O5 S1 C32 107.5(2) . . ?
C31 S1 C32 95.3(4) . . ?
O3 C18 N3 124.5(4) . . ?
O3 C18 C17 122.6(3) . . ?
N3 C18 C17 112.9(3) . . ?
C13 N5 C17 118.5(3) . . ?
C12 N1 N2 120.8(4) . . ?
C3 C2 C7 118.3(3) . . ?
C3 C2 C1 121.4(3) . . ?
C7 C2 C1 120.3(3) . . ?
C1 N2 N1 115.9(3) . . ?
N5 C17 C16 121.9(4) . . ?
N5 C17 C18 117.3(3) . . ?
C16 C17 C18 120.7(4) . . ?
C8 C7 C6 117.6(3) . . ?
C8 C7 C2 123.2(3) . . ?
C6 C7 C2 119.1(3) . . ?
N5 C13 C14 122.5(4) . . ?
N5 C13 C12 117.5(3) . . ?
C14 C13 C12 119.9(3) . . ?
N2 C1 C2 120.7(3) . . ?
C5 C6 C11 121.5(4) . . ?
C5 C6 C7 119.0(4) . . ?
C11 C6 C7 119.6(4) . . ?
O1 C12 N1 123.1(4) . . ?
O1 C12 C13 123.0(3) . . ?
N1 C12 C13 113.9(3) . . ?
O2 C3 C2 122.8(4) . . ?
O2 C3 C4 115.8(4) . . ?
C2 C3 C4 121.4(4) . . ?
C9 C8 C7 121.2(4) . . ?
C15 C16 C17 118.7(4) . . ?
C4 C5 C6 121.7(4) . . ?
C15 C14 C13 118.9(4) . . ?
C11 C10 C9 119.4(4) . . ?
C14 C15 C16 119.5(4) . . ?
C8 C9 C10 120.8(4) . . ?
C10 C11 C6 121.3(4) . . ?
C5 C4 C3 120.4(4) . . ?
C18 N3 N4 120.0(3) . . ?
C19 N4 N3 116.1(3) . . ?
C21 C20 C25 119.1(3) . . ?
C21 C20 C19 120.8(3) . . ?
C25 C20 C19 120.0(3) . . ?
N4 C19 C20 121.4(4) . . ?
O4 C21 C20 122.9(4) . . ?
O4 C21 C22 116.3(4) . . ?
C20 C21 C22 120.8(4) . . ?
C23 C24 C28 121.8(4) . . ?
C23 C24 C25 118.9(4) . . ?
C28 C24 C25 119.3(4) . . ?
C26 C25 C24 116.6(3) . . ?
C26 C25 C20 124.5(3) . . ?
C24 C25 C20 118.9(3) . . ?
C30 C26 C25 122.1(4) . . ?
C22 C23 C24 122.2(4) . . ?
C23 C22 C21 120.0(4) . . ?
C29 C28 C24 122.1(4) . . ?
C28 C29 C30 118.7(4) . . ?
C26 C30 C29 121.2(4) . . ?

_refine_diff_density_max         1.083
_refine_diff_density_min         -1.023
_refine_diff_density_rms         0.066

