# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_UP99186
_database_code_depnum_ccdc_archive 'CCDC 1472443'
_audit_update_record             
;
2016-04-05 deposited with the CCDC.
2016-05-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97

_chemical_formula_sum            'C24 H20 N4 O2 S'
_chemical_formula_weight         428.50

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           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21 '
_symmetry_Int_Tables_number      19

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

_cell_length_a                   4.9002(3)
_cell_length_b                   16.6369(9)
_cell_length_c                   25.4887(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2077.9(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3763
_cell_measurement_temperature    143(1)
_cell_measurement_theta_max      22.70
_cell_measurement_theta_min      2.69
_exptl_crystal_description       prism
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             896
_exptl_absorpt_coefficient_mu    0.186
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2007)'
_exptl_absorpt_correction_T_min  0.6595
_exptl_absorpt_correction_T_max  0.7452
_diffrn_ambient_temperature      143(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'CCD Area Detector'
_diffrn_measurement_device_type  'Bruker APEXII'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_reflns_number            12885
_diffrn_reflns_av_R_equivalents  0.0344
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         2.01
_diffrn_reflns_theta_max         25.07
_reflns_number_total             3670
_reflns_number_gt                3251
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.0356P)²+0.2183P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_chemical_absolute_configuration ad
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(7)
_refine_ls_number_reflns         3670
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0416
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0722
_refine_ls_wR_factor_gt          0.0693
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.0539(5) 0.76882(11) 0.15249(7) 0.0285(5) Uani 1 1 d . . .
C2 C 1.1347(5) 0.82417(13) 0.11470(8) 0.0355(5) Uani 1 1 d . . .
H2 H 1.2700 0.8121 0.0904 0.047 Uiso 1 1 calc R . .
C3 C 1.0059(5) 0.89726(13) 0.11495(9) 0.0411(6) Uani 1 1 d . . .
H3 H 1.0553 0.9359 0.0904 0.055 Uiso 1 1 calc R . .
C4 C 0.8029(5) 0.91462(13) 0.15119(9) 0.0446(6) Uani 1 1 d . . .
H4 H 0.7198 0.9648 0.1501 0.059 Uiso 1 1 calc R . .
C5 C 0.7195(5) 0.86010(12) 0.18888(9) 0.0367(6) Uani 1 1 d . . .
H5 H 0.5839 0.8724 0.2131 0.049 Uiso 1 1 calc R . .
C6 C 0.8497(4) 0.78592(11) 0.18853(7) 0.0251(5) Uani 1 1 d . . .
C7 C 0.6712(4) 0.69727(11) 0.26210(7) 0.0239(5) Uani 1 1 d . . .
C8 C 0.7309(4) 0.61360(11) 0.28453(7) 0.0270(5) Uani 1 1 d . . .
H8 H 0.9276 0.6040 0.2817 0.036 Uiso 1 1 calc R . .
C9 C 0.5856(5) 0.54915(12) 0.25294(9) 0.0377(6) Uani 1 1 d . . .
H9A H 0.6421 0.4971 0.2649 0.057 Uiso 1 1 calc R . .
H9B H 0.6309 0.5550 0.2165 0.057 Uiso 1 1 calc R . .
H9C H 0.3919 0.5547 0.2574 0.057 Uiso 1 1 calc R . .
C10 C 0.8500(4) 0.61378(11) 0.37656(8) 0.0241(5) Uani 1 1 d . . .
C11 C 0.9370(5) 0.62382(12) 0.46739(7) 0.0296(5) Uani 1 1 d . . .
H11A H 0.9981 0.6791 0.4702 0.039 Uiso 1 1 calc R . .
H11B H 1.0945 0.5903 0.4602 0.039 Uiso 1 1 calc R . .
C12 C 0.8033(4) 0.59779(11) 0.51829(7) 0.0268(5) Uani 1 1 d . . .
H12 H 0.6414 0.6305 0.5255 0.036 Uiso 1 1 calc R . .
C13 C 1.0093(4) 0.60572(12) 0.56236(7) 0.0272(5) Uani 1 1 d . . .
C14 C 1.1444(5) 0.67310(13) 0.57986(8) 0.0335(5) Uani 1 1 d . . .
H14 H 1.1050 0.7234 0.5659 0.044 Uiso 1 1 calc R . .
C15 C 1.3411(5) 0.66467(14) 0.61895(8) 0.0394(6) Uani 1 1 d . . .
H15 H 1.4360 0.7096 0.6307 0.052 Uiso 1 1 calc R . .
C16 C 1.3967(5) 0.59027(14) 0.64048(8) 0.0410(6) Uani 1 1 d . . .
H16 H 1.5289 0.5857 0.6665 0.055 Uiso 1 1 calc R . .
C17 C 1.2579(5) 0.52233(14) 0.62379(8) 0.0357(6) Uani 1 1 d . . .
H17 H 1.2941 0.4724 0.6387 0.048 Uiso 1 1 calc R . .
C18 C 1.0636(5) 0.53006(12) 0.58438(7) 0.0276(5) Uani 1 1 d . . .
C19 C 0.8886(5) 0.47059(11) 0.55864(7) 0.0270(5) Uani 1 1 d . . .
C20 C 0.8589(5) 0.38846(12) 0.56752(8) 0.0356(5) Uani 1 1 d . . .
H20 H 0.9646 0.3625 0.5926 0.047 Uiso 1 1 calc R . .
C21 C 0.6695(6) 0.34626(13) 0.53834(8) 0.0393(6) Uani 1 1 d . . .
H21 H 0.6463 0.2915 0.5443 0.052 Uiso 1 1 calc R . .
C22 C 0.5134(5) 0.38421(13) 0.50031(8) 0.0365(6) Uani 1 1 d . . .
H22 H 0.3865 0.3548 0.4812 0.049 Uiso 1 1 calc R . .
C23 C 0.5454(5) 0.46600(12) 0.49061(8) 0.0303(5) Uani 1 1 d . . .
H23 H 0.4425 0.4914 0.4648 0.040 Uiso 1 1 calc R . .
C24 C 0.7327(4) 0.50876(12) 0.51999(8) 0.0246(5) Uani 1 1 d . . .
N1 N 0.8317(3) 0.71646(9) 0.21862(6) 0.0249(4) Uani 1 1 d . . .
N2 N 1.0211(4) 0.66060(10) 0.20019(6) 0.0297(4) Uani 1 1 d . . .
N3 N 1.1513(4) 0.69140(10) 0.16133(6) 0.0332(4) Uani 1 1 d . . .
N4 N 0.6580(4) 0.60992(10) 0.33947(6) 0.0295(4) Uani 1 1 d . . .
H4A H 0.4894 0.6052 0.3483 0.039 Uiso 1 1 calc R . .
O1 O 1.0947(3) 0.61345(9) 0.36889(6) 0.0357(4) Uani 1 1 d . . .
O2 O 0.7390(3) 0.61635(8) 0.42516(5) 0.0283(3) Uani 1 1 d . . .
S1 S 0.44167(12) 0.75751(3) 0.28520(2) 0.03201(14) Uani 1 1 d . . .


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
C1 C6 1.388(3) . ?
C1 C2 1.390(3) . ?
C1 N3 1.392(3) . ?
C2 C3 1.370(3) . ?
C3 C4 1.388(3) . ?
C4 C5 1.383(3) . ?
C5 C6 1.389(3) . ?
C6 N1 1.390(2) . ?
C7 N1 1.396(2) . ?
C7 C8 1.533(3) . ?
C7 S1 1.618(2) . ?
C8 N4 1.447(2) . ?
C8 C9 1.518(3) . ?
C10 O1 1.215(2) . ?
C10 N4 1.335(3) . ?
C10 O2 1.354(2) . ?
C11 O2 1.454(2) . ?
C11 C12 1.517(3) . ?
C12 C13 1.516(3) . ?
C12 C24 1.522(3) . ?
C13 C14 1.376(3) . ?
C13 C18 1.404(3) . ?
C14 C15 1.393(3) . ?
C15 C16 1.381(3) . ?
C16 C17 1.386(3) . ?
C17 C18 1.390(3) . ?
C18 C19 1.465(3) . ?
C19 C20 1.393(3) . ?
C19 C24 1.399(3) . ?
C20 C21 1.381(3) . ?
C21 C22 1.387(3) . ?
C22 C23 1.392(3) . ?
C23 C24 1.382(3) . ?
N1 N2 1.395(2) . ?
N2 N3 1.285(2) . ?

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
C6 C1 C2 121.89(19) . . ?
C6 C1 N3 109.26(17) . . ?
C2 C1 N3 128.8(2) . . ?
C3 C2 C1 117.0(2) . . ?
C2 C3 C4 121.2(2) . . ?
C5 C4 C3 122.5(2) . . ?
C4 C5 C6 116.3(2) . . ?
C1 C6 N1 103.92(17) . . ?
C1 C6 C5 121.16(19) . . ?
N1 C6 C5 134.91(19) . . ?
N1 C7 C8 113.35(16) . . ?
N1 C7 S1 122.62(14) . . ?
C8 C7 S1 124.01(14) . . ?
N4 C8 C9 111.58(17) . . ?
N4 C8 C7 110.63(16) . . ?
C9 C8 C7 110.74(16) . . ?
O1 C10 N4 125.54(19) . . ?
O1 C10 O2 122.9(2) . . ?
N4 C10 O2 111.50(18) . . ?
O2 C11 C12 108.69(17) . . ?
C13 C12 C11 108.75(17) . . ?
C13 C12 C24 102.42(16) . . ?
C11 C12 C24 113.61(16) . . ?
C14 C13 C18 120.65(19) . . ?
C14 C13 C12 129.15(18) . . ?
C18 C13 C12 110.14(17) . . ?
C13 C14 C15 118.8(2) . . ?
C16 C15 C14 120.7(2) . . ?
C15 C16 C17 120.8(2) . . ?
C16 C17 C18 118.9(2) . . ?
C17 C18 C13 120.1(2) . . ?
C17 C18 C19 131.49(19) . . ?
C13 C18 C19 108.40(18) . . ?
C20 C19 C24 120.2(2) . . ?
C20 C19 C18 130.62(19) . . ?
C24 C19 C18 109.18(16) . . ?
C21 C20 C19 118.8(2) . . ?
C20 C21 C22 121.0(2) . . ?
C21 C22 C23 120.5(2) . . ?
C24 C23 C22 118.8(2) . . ?
C23 C24 C19 120.70(18) . . ?
C23 C24 C12 129.55(19) . . ?
C19 C24 C12 109.74(18) . . ?
C6 N1 N2 109.02(15) . . ?
C6 N1 C7 131.61(17) . . ?
N2 N1 C7 119.33(15) . . ?
N3 N2 N1 108.92(15) . . ?
N2 N3 C1 108.87(17) . . ?
C10 N4 C8 120.62(17) . . ?
C10 O2 C11 114.33(16) . . ?

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
N4 H4A O1 0.86 2.01 2.861(2) 170.8 1_455

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.07
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.141
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.034
_exptl_crystal_colour            'yellowish green'
