# 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 2014

data_global
_audit_creation_method           'APEX2 v2010.11-3'

_publ_requested_journal          ?

_publ_contact_author_name        ?
_publ_contact_author_address     
;
;
_publ_contact_author_email       ?
_publ_contact_author_fax         ?
_publ_contact_author_phone       ?

_publ_section_title              
;
;
_publ_section_abstract           
;
;
_publ_section_references         
;
;
_publ_section_comment            
;
;

data_I
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C23 H24 N4 O3 S'
_chemical_formula_sum            'C23 H24 N4 O3 S'
_chemical_formula_iupac          ?
_chemical_formula_weight         436.53

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.7031(7)
_cell_length_b                   17.8226(19)
_cell_length_c                   16.0433(16)
_cell_angle_alpha                90
_cell_angle_beta                 90.717(6)
_cell_angle_gamma                90
_cell_volume                     2202.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4239
_cell_measurement_theta_min      2.2855
_cell_measurement_theta_max      22.8824
_cell_measurement_temperature    200.(2)

_exptl_crystal_description       rectangular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             920

_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2008/1 (Bruker AXS)'
_exptl_absorpt_correction_T_min  0.6508
_exptl_absorpt_correction_T_max  0.7452

_exptl_special_details           
;
;

_diffrn_ambient_temperature      200.(2)

_diffrn_source                   'sealed tube'
_diffrn_source_type              'fine focus'

_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

_diffrn_measurement_device_type  'Bruker Kappa ApexII'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            22864
_diffrn_reflns_av_R_equivalents  0.0546
_diffrn_reflns_av_sigmaI/netI    0.0487
_diffrn_reflns_theta_min         1.71
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_full        25.10
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19

_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.
;

_reflns_number_total             3892
_reflns_number_gt                2535
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0429
_refine_ls_wR_factor_gt          0.1019
_refine_ls_wR_factor_ref         0.1196
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_restrained_S_all      0.971
_refine_ls_number_reflns         3892
_refine_ls_number_parameters     284
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    undef
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0663P)²+0.0269P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.309
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service v2012.12.0.2'
_computing_cell_refinement       'SAINT V7.68A (Bruker AXS, 2009)'
_computing_data_reduction        'SAINT V7.68A (Bruker AXS, 2009)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S S1 0.99249(7) 0.97499(4) 0.68531(4) 0.0374(2) Uani d . 1 . .
O O1 1.03476(19) 0.89691(9) 0.68637(10) 0.0459(5) Uani d . 1 . .
O O2 1.12903(17) 1.02965(10) 0.69084(10) 0.0453(5) Uani d . 1 . .
O O3 0.99166(16) 0.87768(8) 0.47315(9) 0.0349(4) Uani d . 1 . .
N N1 0.4026(2) 1.14025(12) 0.90601(12) 0.0470(6) Uani d . 1 . .
N N2 0.8842(2) 0.99395(10) 0.60124(11) 0.0329(5) Uani d . 1 . .
H H2 0.8906 1.0392 0.5797 0.039 Uiso calc R 1 . .
N N3 0.7023(2) 0.84386(11) 0.47940(12) 0.0354(5) Uani d . 1 . .
N N4 0.5607(2) 0.86210(11) 0.53060(12) 0.0386(5) Uani d . 1 . .
C C1 0.3567(3) 1.21336(16) 0.93925(18) 0.0616(8) Uani d . 1 . .
H H1A 0.4608 1.2378 0.9621 0.092 Uiso calc R 1 . .
H H1B 0.2713 1.2072 0.9835 0.092 Uiso calc R 1 . .
H H1C 0.3069 1.2444 0.8946 0.092 Uiso calc R 1 . .
C C2 0.5435(3) 1.13945(15) 0.84950(15) 0.0407(6) Uani d . 1 . .
C C3 0.6329(3) 1.06944(14) 0.83867(14) 0.0368(6) Uani d . 1 . .
C C4 0.7674(3) 1.06381(13) 0.77871(14) 0.0354(6) Uani d . 1 . .
C C5 0.8435(3) 0.99133(13) 0.76683(14) 0.0352(6) Uani d . 1 . .
C C6 0.7795(2) 0.93937(13) 0.56164(13) 0.0301(5) Uani d . 1 . .
C C7 0.8438(2) 0.88712(13) 0.50144(14) 0.0305(5) Uani d . 1 . .
C C8 0.7096(3) 0.77188(14) 0.44091(16) 0.0382(6) Uani d . 1 . .
C C9 0.6652(3) 0.70793(16) 0.48391(18) 0.0515(7) Uani d . 1 . .
H H9 0.6255 0.7111 0.5396 0.062 Uiso calc R 1 . .
C C10 0.6791(4) 0.63894(17) 0.4448(2) 0.0660(9) Uani d . 1 . .
H H10 0.6479 0.5945 0.4737 0.079 Uiso calc R 1 . .
C C11 0.7376(4) 0.63423(19) 0.3646(2) 0.0690(9) Uani d . 1 . .
H H11 0.7477 0.5867 0.3384 0.083 Uiso calc R 1 . .
C C12 0.2476(3) 1.10100(17) 0.87518(18) 0.0625(8) Uani d . 1 . .
H H12A 0.1835 1.1336 0.8364 0.094 Uiso calc R 1 . .
H H12B 0.1734 1.0881 0.9222 0.094 Uiso calc R 1 . .
H H12C 0.2823 1.055 0.8463 0.094 Uiso calc R 1 . .
C C13 0.5933(3) 1.00605(15) 0.88798(15) 0.0452(7) Uani d . 1 . .
H H13 0.5077 1.0104 0.9298 0.054 Uiso calc R 1 . .
C C14 0.6742(3) 0.93926(16) 0.87724(16) 0.0499(7) Uani d . 1 . .
H H14 0.647 0.8979 0.9121 0.06 Uiso calc R 1 . .
C C15 0.7985(3) 0.93125(14) 0.81437(15) 0.0432(6) Uani d . 1 . .
H H15 0.8511 0.8838 0.805 0.052 Uiso calc R 1 . .
C C16 0.8157(3) 1.12906(14) 0.73465(15) 0.0431(6) Uani d . 1 . .
H H16 0.9033 1.1264 0.6936 0.052 Uiso calc R 1 . .
C C17 0.7367(3) 1.19598(15) 0.75089(17) 0.0520(7) Uani d . 1 . .
H H17 0.7749 1.2399 0.7231 0.062 Uiso calc R 1 . .
C C18 0.6003(3) 1.20128(15) 0.80777(17) 0.0495(7) Uani d . 1 . .
H H18 0.5469 1.2485 0.8173 0.059 Uiso calc R 1 . .
C C19 0.7815(4) 0.69845(19) 0.3222(2) 0.0664(9) Uani d . 1 . .
H H19 0.8222 0.6951 0.2666 0.08 Uiso calc R 1 . .
C C20 0.7667(3) 0.76779(16) 0.35998(17) 0.0519(7) Uani d . 1 . .
H H20 0.7956 0.8122 0.3305 0.062 Uiso calc R 1 . .
C C21 0.3899(3) 0.85851(15) 0.48851(17) 0.0524(8) Uani d . 1 . .
H H21A 0.2982 0.866 0.5295 0.079 Uiso calc R 1 . .
H H21B 0.3754 0.8093 0.4621 0.079 Uiso calc R 1 . .
H H21C 0.3823 0.8979 0.4459 0.079 Uiso calc R 1 . .
C C22 0.6097(3) 0.92387(13) 0.57598(15) 0.0352(6) Uani d . 1 . .
C C23 0.4826(3) 0.96278(15) 0.62995(16) 0.0505(7) Uani d . 1 . .
H H23A 0.5421 1.002 0.6621 0.076 Uiso calc R 1 . .
H H23B 0.4307 0.9265 0.6682 0.076 Uiso calc R 1 . .
H H23C 0.3913 0.9855 0.5951 0.076 Uiso calc R 1 . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
S1 O1 . 1.4292(16) ?
S1 O2 . 1.4355(16) ?
S1 N2 . 1.6128(19) ?
S1 C5 . 1.775(2) ?
O3 C7 . 1.242(2) ?
N1 C2 . 1.423(3) ?
N1 C1 . 1.453(3) ?
N1 C12 . 1.464(3) ?
N2 C6 . 1.410(3) ?
N2 H2 . 0.88 ?
N3 C7 . 1.378(3) ?
N3 N4 . 1.412(2) ?
N3 C8 . 1.425(3) ?
N4 C22 . 1.370(3) ?
N4 C21 . 1.473(3) ?
C1 H1A . 0.98 ?
C1 H1B . 0.98 ?
C1 H1C . 0.98 ?
C2 C18 . 1.364(3) ?
C2 C3 . 1.436(3) ?
C3 C13 . 1.415(3) ?
C3 C4 . 1.426(3) ?
C4 C16 . 1.413(3) ?
C4 C5 . 1.432(3) ?
C5 C15 . 1.362(3) ?
C6 C22 . 1.359(3) ?
C6 C7 . 1.434(3) ?
C8 C9 . 1.378(3) ?
C8 C20 . 1.378(3) ?
C9 C10 . 1.386(4) ?
C9 H9 . 0.95 ?
C10 C11 . 1.370(4) ?
C10 H10 . 0.95 ?
C11 C19 . 1.376(4) ?
C11 H11 . 0.95 ?
C12 H12A . 0.98 ?
C12 H12B . 0.98 ?
C12 H12C . 0.98 ?
C13 C14 . 1.356(3) ?
C13 H13 . 0.95 ?
C14 C15 . 1.406(3) ?
C14 H14 . 0.95 ?
C15 H15 . 0.95 ?
C16 C17 . 1.365(3) ?
C16 H16 . 0.95 ?
C17 C18 . 1.403(3) ?
C17 H17 . 0.95 ?
C18 H18 . 0.95 ?
C19 C20 . 1.382(4) ?
C19 H19 . 0.95 ?
C20 H20 . 0.95 ?
C21 H21A . 0.98 ?
C21 H21B . 0.98 ?
C21 H21C . 0.98 ?
C22 C23 . 1.487(3) ?
C23 H23A . 0.98 ?
C23 H23B . 0.98 ?
C23 H23C . 0.98 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 S1 O2 . . 119.56(10) ?
O1 S1 N2 . . 109.23(10) ?
O2 S1 N2 . . 106.29(10) ?
O1 S1 C5 . . 107.48(11) ?
O2 S1 C5 . . 108.85(10) ?
N2 S1 C5 . . 104.44(10) ?
C2 N1 C1 . . 115.7(2) ?
C2 N1 C12 . . 113.90(19) ?
C1 N1 C12 . . 110.5(2) ?
C6 N2 S1 . . 121.29(15) ?
C6 N2 H2 . . 119.4 ?
S1 N2 H2 . . 119.4 ?
C7 N3 N4 . . 109.67(17) ?
C7 N3 C8 . . 125.41(17) ?
N4 N3 C8 . . 119.63(17) ?
C22 N4 N3 . . 106.53(15) ?
C22 N4 C21 . . 121.1(2) ?
N3 N4 C21 . . 114.56(19) ?
N1 C1 H1A . . 109.5 ?
N1 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
N1 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C18 C2 N1 . . 123.8(2) ?
C18 C2 C3 . . 119.0(2) ?
N1 C2 C3 . . 117.1(2) ?
C13 C3 C4 . . 119.0(2) ?
C13 C3 C2 . . 121.3(2) ?
C4 C3 C2 . . 119.7(2) ?
C16 C4 C3 . . 118.5(2) ?
C16 C4 C5 . . 124.4(2) ?
C3 C4 C5 . . 117.1(2) ?
C15 C5 C4 . . 121.8(2) ?
C15 C5 S1 . . 117.08(18) ?
C4 C5 S1 . . 121.03(17) ?
C22 C6 N2 . . 127.6(2) ?
C22 C6 C7 . . 108.9(2) ?
N2 C6 C7 . . 123.40(17) ?
O3 C7 N3 . . 123.8(2) ?
O3 C7 C6 . . 131.3(2) ?
N3 C7 C6 . . 104.88(17) ?
C9 C8 C20 . . 120.8(2) ?
C9 C8 N3 . . 121.1(2) ?
C20 C8 N3 . . 118.1(2) ?
C8 C9 C10 . . 119.1(3) ?
C8 C9 H9 . . 120.5 ?
C10 C9 H9 . . 120.5 ?
C11 C10 C9 . . 120.5(3) ?
C11 C10 H10 . . 119.7 ?
C9 C10 H10 . . 119.7 ?
C10 C11 C19 . . 120.0(3) ?
C10 C11 H11 . . 120.0 ?
C19 C11 H11 . . 120.0 ?
N1 C12 H12A . . 109.5 ?
N1 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
N1 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
C14 C13 C3 . . 121.9(2) ?
C14 C13 H13 . . 119.1 ?
C3 C13 H13 . . 119.1 ?
C13 C14 C15 . . 119.9(2) ?
C13 C14 H14 . . 120.1 ?
C15 C14 H14 . . 120.1 ?
C5 C15 C14 . . 120.1(2) ?
C5 C15 H15 . . 119.9 ?
C14 C15 H15 . . 119.9 ?
C17 C16 C4 . . 120.2(2) ?
C17 C16 H16 . . 119.9 ?
C4 C16 H16 . . 119.9 ?
C16 C17 C18 . . 121.5(2) ?
C16 C17 H17 . . 119.3 ?
C18 C17 H17 . . 119.3 ?
C2 C18 C17 . . 120.8(2) ?
C2 C18 H18 . . 119.6 ?
C17 C18 H18 . . 119.6 ?
C11 C19 C20 . . 120.3(3) ?
C11 C19 H19 . . 119.9 ?
C20 C19 H19 . . 119.9 ?
C8 C20 C19 . . 119.3(3) ?
C8 C20 H20 . . 120.3 ?
C19 C20 H20 . . 120.3 ?
N4 C21 H21A . . 109.5 ?
N4 C21 H21B . . 109.5 ?
H21A C21 H21B . . 109.5 ?
N4 C21 H21C . . 109.5 ?
H21A C21 H21C . . 109.5 ?
H21B C21 H21C . . 109.5 ?
C6 C22 N4 . . 109.4(2) ?
C6 C22 C23 . . 130.2(2) ?
N4 C22 C23 . . 120.35(19) ?
C22 C23 H23A . . 109.5 ?
C22 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
C22 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 109.5 ?

_database_code_depnum_ccdc_archive 'CCDC 963670'
