# 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_mm_b_a
_audit_block_doi                 10.5517/ccdc.csd.cc1zhmrv
_database_code_depnum_ccdc_archive 'CCDC 1832278'
_audit_update_record             
;
2018-03-24 deposited with the CCDC.
2018-12-27 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         'C23 H19 N4 O4 S'
_chemical_formula_sum            'C23 H19 N4 O4 S'
_chemical_formula_weight         447.92

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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   9.3279(6)
_cell_length_b                   21.2988(14)
_cell_length_c                   11.6031(8)
_cell_angle_alpha                90
_cell_angle_beta                 113.536(2)
_cell_angle_gamma                90
_cell_volume                     2113.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    3721
_cell_measurement_theta_min      2.566
_cell_measurement_theta_max      25.000

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_F_000             933.7
_exptl_transmission_factor_min   0.977
_exptl_transmission_factor_max   0.981
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_absorpt_coefficient_mu    0.192
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            49871
_diffrn_reflns_av_unetI/netI     0.0375
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.566
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3710
_reflns_number_gt                2604
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_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)+(0.0455P)²+0.8968P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0061(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3710
_refine_ls_number_parameters     336
_refine_ls_number_restraints     102
_refine_ls_R_factor_all          0.0873
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1122
_refine_ls_wR_factor_gt          0.0983
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.067
_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
C3 C 0.5551(3) 0.33075(11) 0.7387(2) 0.0507(7) Uani 1 1 d . . . . .
H3A H 0.6514 0.3229 0.7295 0.076 Uiso 1 1 calc R U . . .
H3B H 0.4687 0.3233 0.6599 0.076 Uiso 1 1 calc R U . . .
H3C H 0.5476 0.3032 0.8015 0.076 Uiso 1 1 calc R U . . .
C4 C 0.5517(2) 0.39688(10) 0.7774(2) 0.0349(5) Uani 1 1 d . . . . .
C5 C 0.4388(2) 0.43103(10) 0.79946(18) 0.0293(5) Uani 1 1 d . . . . .
C6 C 0.5048(2) 0.48975(10) 0.83563(18) 0.0291(5) Uani 1 1 d . . . . .
C7 C 0.2765(2) 0.41460(9) 0.78824(19) 0.0301(5) Uani 1 1 d . . . . .
C8 C 0.2793(2) 0.35986(10) 0.8779(2) 0.0355(5) Uani 1 1 d . . . . .
C9 C 0.1298(2) 0.32660(11) 0.6796(2) 0.0437(6) Uani 1 1 d . . . . .
C10 C 0.0335(3) 0.29027(13) 0.5809(3) 0.0621(8) Uani 1 1 d . . . . .
H10 H -0.0001 0.2508 0.5940 0.075 Uiso 1 1 calc R U . . .
C11 C -0.0108(3) 0.31489(17) 0.4618(3) 0.0741(10) Uani 1 1 d . . . . .
H11 H -0.0742 0.2911 0.3932 0.089 Uiso 1 1 calc R U . . .
C12 C 0.0355(3) 0.37340(18) 0.4413(3) 0.0747(9) Uani 1 1 d . . . . .
H12 H 0.0048 0.3883 0.3596 0.090 Uiso 1 1 calc R U . . .
C13 C 0.1293(3) 0.41083(14) 0.5431(2) 0.0547(7) Uani 1 1 d . . . . .
H13 H 0.1592 0.4510 0.5305 0.066 Uiso 1 1 calc R U . . .
C14 C 0.1754(2) 0.38634(11) 0.6614(2) 0.0373(6) Uani 1 1 d . . . . .
C15 C 0.2063(2) 0.47303(9) 0.82207(19) 0.0294(5) Uani 1 1 d . . . . .
C16 C 0.2819(2) 0.52957(10) 0.85831(18) 0.0289(5) Uani 1 1 d . . . . .
C17 C 0.2025(2) 0.58184(10) 0.88887(19) 0.0315(5) Uani 1 1 d . . . . .
C18 C 0.0531(2) 0.46507(11) 0.8200(2) 0.0361(5) Uani 1 1 d . . . . .
C19 C 0.0566(2) 0.57058(10) 0.8902(2) 0.0355(5) Uani 1 1 d . . . . .
C20 C -0.0258(3) 0.61617(11) 0.9226(2) 0.0449(6) Uani 1 1 d . . . . .
H20 H -0.1214 0.6067 0.9259 0.054 Uiso 1 1 calc R U . . .
C21 C 0.0354(3) 0.67553(12) 0.9498(2) 0.0516(7) Uani 1 1 d . . . . .
H21 H -0.0190 0.7068 0.9714 0.062 Uiso 1 1 calc R U . . .
C22 C 0.1784(3) 0.68889(11) 0.9450(2) 0.0502(7) Uani 1 1 d . . . . .
H22 H 0.2186 0.7294 0.9616 0.060 Uiso 1 1 calc R U . . .
C23 C 0.2610(3) 0.64276(10) 0.9159(2) 0.0416(6) Uani 1 1 d . . . . .
H23 H 0.3574 0.6523 0.9143 0.050 Uiso 1 1 calc R U . . .
N1 N 0.1958(2) 0.31193(8) 0.8082(2) 0.0460(5) Uani 1 1 d . . . . .
H4 H 0.1842 0.2764 0.8387 0.055 Uiso 1 1 calc R U . . .
N2 N 0.6720(2) 0.43687(9) 0.80031(17) 0.0378(5) Uani 1 1 d . . . . .
N3 N 0.64731(19) 0.49541(8) 0.83702(17) 0.0364(5) Uani 1 1 d . . . . .
N4 N 0.4292(2) 0.53922(9) 0.86521(17) 0.0324(4) Uani 1 1 d . . . . .
O2 O -0.02538(17) 0.41725(7) 0.78908(16) 0.0479(4) Uani 1 1 d . . . . .
O3 O 0.34796(17) 0.36081(7) 0.99278(16) 0.0444(4) Uani 1 1 d . . . . .
O4 O -0.01490(16) 0.51342(7) 0.85715(15) 0.0432(4) Uani 1 1 d . . . . .
S1 S 0.06419(14) 0.14790(6) 0.85656(15) 0.0653(5) Uani 0.812(5) 1 d D U P A 1
C1 C -0.1278(8) 0.1345(5) 0.8291(8) 0.131(4) Uani 0.812(5) 1 d D U P A 1
H1A H -0.1611 0.0956 0.7846 0.196 Uiso 0.812(5) 1 calc R U P A 1
H1B H -0.1389 0.1322 0.9078 0.196 Uiso 0.812(5) 1 calc R U P A 1
H1C H -0.1910 0.1681 0.7795 0.196 Uiso 0.812(5) 1 calc R U P A 1
C2 C 0.1600(10) 0.0875(3) 0.9666(11) 0.083(2) Uani 0.812(5) 1 d D U P A 1
H2A H 0.1337 0.0474 0.9258 0.125 Uiso 0.812(5) 1 calc R U P A 1
H2B H 0.2711 0.0936 0.9983 0.125 Uiso 0.812(5) 1 calc R U P A 1
H2C H 0.1269 0.0890 1.0350 0.125 Uiso 0.812(5) 1 calc R U P A 1
O1 O 0.1101(3) 0.20909(15) 0.9261(3) 0.0676(9) Uani 0.812(5) 1 d D U P A 1
S1' S 0.0713(7) 0.1670(4) 0.9286(9) 0.096(3) Uani 0.188(5) 1 d D U P A 2
O1' O 0.1092(17) 0.1890(8) 0.8226(14) 0.109(5) Uani 0.188(5) 1 d D U P A 2
C1' C -0.119(3) 0.137(2) 0.884(3) 0.097(8) Uani 0.188(5) 1 d D U P A 2
H1'1 H -0.1338 0.1242 0.9581 0.146 Uiso 0.188(5) 1 calc R U P A 2
H1'2 H -0.1935 0.1695 0.8420 0.146 Uiso 0.188(5) 1 calc R U P A 2
H1'3 H -0.1337 0.1021 0.8292 0.146 Uiso 0.188(5) 1 calc R U P A 2
C2' C 0.110(6) 0.0881(11) 0.955(5) 0.102(11) Uani 0.188(5) 1 d D U P A 2
H H 0.765(3) 0.4281(10) 0.798(2) 0.044(6) Uiso 1 1 d . . . . .
H3 H 0.482(3) 0.5717(12) 0.902(2) 0.049(7) 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
C3 C4 1.483(3) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 N2 1.348(3) . ?
C4 C5 1.385(3) . ?
C5 C6 1.383(3) . ?
C5 C7 1.508(3) . ?
C6 N3 1.329(3) . ?
C6 N4 1.385(3) . ?
C7 C14 1.520(3) . ?
C7 C15 1.529(3) . ?
C7 C8 1.556(3) . ?
C8 O3 1.227(3) . ?
C8 N1 1.341(3) . ?
C9 C10 1.377(3) . ?
C9 C14 1.385(3) . ?
C9 N1 1.403(3) . ?
C10 C11 1.378(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.371(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.404(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.367(3) . ?
C13 H13 0.9300 . ?
C15 C16 1.374(3) . ?
C15 C18 1.429(3) . ?
C16 N4 1.359(3) . ?
C16 C17 1.457(3) . ?
C17 C19 1.388(3) . ?
C17 C23 1.394(3) . ?
C18 O2 1.222(2) . ?
C18 O4 1.366(3) . ?
C19 O4 1.367(3) . ?
C19 C20 1.381(3) . ?
C20 C21 1.371(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.387(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.371(3) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
N1 H4 0.8600 . ?
N2 N3 1.367(2) . ?
N2 H 0.90(2) . ?
N4 H3 0.86(2) . ?
S1 O1 1.503(4) . ?
S1 C1 1.713(7) . ?
S1 C2 1.782(7) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
S1' O1' 1.486(16) . ?
S1' C2' 1.72(2) . ?
S1' C1' 1.757(18) . ?
C1' H1'1 0.9600 . ?
C1' H1'2 0.9600 . ?
C1' H1'3 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
C4 C3 H3A 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C4 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
N2 C4 C5 105.44(19) . . ?
N2 C4 C3 122.87(19) . . ?
C5 C4 C3 131.68(19) . . ?
C6 C5 C4 104.60(17) . . ?
C6 C5 C7 123.07(18) . . ?
C4 C5 C7 132.32(19) . . ?
N3 C6 C5 114.05(18) . . ?
N3 C6 N4 122.26(18) . . ?
C5 C6 N4 123.67(18) . . ?
C5 C7 C14 112.89(16) . . ?
C5 C7 C15 107.90(16) . . ?
C14 C7 C15 114.02(16) . . ?
C5 C7 C8 111.60(16) . . ?
C14 C7 C8 100.88(17) . . ?
C15 C7 C8 109.44(16) . . ?
O3 C8 N1 126.4(2) . . ?
O3 C8 C7 125.17(19) . . ?
N1 C8 C7 108.47(19) . . ?
C10 C9 C14 121.8(3) . . ?
C10 C9 N1 128.6(2) . . ?
C14 C9 N1 109.63(19) . . ?
C9 C10 C11 117.1(3) . . ?
C9 C10 H10 121.5 . . ?
C11 C10 H10 121.5 . . ?
C12 C11 C10 122.1(3) . . ?
C12 C11 H11 119.0 . . ?
C10 C11 H11 119.0 . . ?
C11 C12 C13 120.2(3) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 117.9(3) . . ?
C14 C13 H13 121.0 . . ?
C12 C13 H13 121.0 . . ?
C13 C14 C9 120.8(2) . . ?
C13 C14 C7 130.2(2) . . ?
C9 C14 C7 109.0(2) . . ?
C16 C15 C18 119.79(18) . . ?
C16 C15 C7 124.86(17) . . ?
C18 C15 C7 115.28(17) . . ?
N4 C16 C15 122.28(19) . . ?
N4 C16 C17 118.03(18) . . ?
C15 C16 C17 119.69(17) . . ?
C19 C17 C23 117.09(19) . . ?
C19 C17 C16 117.80(19) . . ?
C23 C17 C16 125.11(19) . . ?
O2 C18 O4 114.95(18) . . ?
O2 C18 C15 125.6(2) . . ?
O4 C18 C15 119.47(19) . . ?
O4 C19 C20 116.11(19) . . ?
O4 C19 C17 121.45(18) . . ?
C20 C19 C17 122.4(2) . . ?
C21 C20 C19 119.0(2) . . ?
C21 C20 H20 120.5 . . ?
C19 C20 H20 120.5 . . ?
C20 C21 C22 119.9(2) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C23 C22 C21 120.4(2) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C22 C23 C17 121.0(2) . . ?
C22 C23 H23 119.5 . . ?
C17 C23 H23 119.5 . . ?
C8 N1 C9 111.98(19) . . ?
C8 N1 H4 124.0 . . ?
C9 N1 H4 124.0 . . ?
C4 N2 N3 114.03(17) . . ?
C4 N2 H 127.0(15) . . ?
N3 N2 H 118.9(14) . . ?
C6 N3 N2 101.88(16) . . ?
C16 N4 C6 118.21(18) . . ?
C16 N4 H3 120.8(16) . . ?
C6 N4 H3 119.6(16) . . ?
C18 O4 C19 121.56(16) . . ?
O1 S1 C1 107.3(3) . . ?
O1 S1 C2 106.7(4) . . ?
C1 S1 C2 101.6(5) . . ?
S1 C1 H1A 109.5 . . ?
S1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
S1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
S1 C2 H2A 109.5 . . ?
S1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
S1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O1' S1' C2' 111(2) . . ?
O1' S1' C1' 114.8(14) . . ?
C2' S1' C1' 79(2) . . ?
S1' C1' H1'1 109.5 . . ?
S1' C1' H1'2 109.5 . . ?
H1'1 C1' H1'2 109.5 . . ?
S1' C1' H1'3 109.5 . . ?
H1'1 C1' H1'3 109.5 . . ?
H1'2 C1' H1'3 109.5 . . ?

_refine_diff_density_max         0.215
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.038

