# 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 2022

####################################################################### 
# 
# 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_JF766
_database_code_depnum_ccdc_archive 'CCDC 2123510'
loop_
_audit_author_name
_audit_author_address
'Thierry ROISNEL' 'CDIFX ISCR CNRS Univ Rennes, France'
_audit_update_record             
;
2021-11-22 deposited with the CCDC.	2022-04-04 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 12 novembre 2019                                         #
#------------------------------------------------------------------------------#


#------------------------------------------------------------------------------#
#                             CHEMICAL INFORMATION                             #
#------------------------------------------------------------------------------#


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C17 H20 N4 O2 S'
_chemical_formula_sum            'C17 H20 N4 O2 S'
_chemical_formula_weight         344.43
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                            UNIT CELL INFORMATION                             #
#------------------------------------------------------------------------------#


_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
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                   6.1420(5)
_cell_length_b                   22.7420(18)
_cell_length_c                   12.2786(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.538(3)
_cell_angle_gamma                90
_cell_volume                     1703.9(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_cell_measurement_reflns_used    9951
_cell_measurement_theta_min      3.1639
_cell_measurement_theta_max      27.5079
_cell_measurement_wavelength     0.71073


#------------------------------------------------------------------------------#
#                              ORIENTATION MATRIX                              #
#------------------------------------------------------------------------------#

_diffrn_orient_matrix_UB_11      -0.1270089
_diffrn_orient_matrix_UB_21      -0.0842260
_diffrn_orient_matrix_UB_31      0.0602580
_diffrn_orient_matrix_UB_12      0.0212730
_diffrn_orient_matrix_UB_22      -0.0376788
_diffrn_orient_matrix_UB_32      -0.0078275
_diffrn_orient_matrix_UB_13      0.0258783
_diffrn_orient_matrix_UB_23      -0.0015452
_diffrn_orient_matrix_UB_33      0.0777684


#------------------------------------------------------------------------------#
#                             CRYSTAL INFORMATION                              #
#------------------------------------------------------------------------------#

_exptl_crystal_description       stick
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.070
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             728
_exptl_special_details           
;
 ?
;

#------------------------------------------------------------------------------#
#                            ABSORPTION CORRECTION                             #
#------------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2014). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.422
_exptl_absorpt_correction_T_max  0.986

#------------------------------------------------------------------------------#
#                               DATA COLLECTION                                #
#------------------------------------------------------------------------------#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 '(CMOS) PHOTON 100'
_diffrn_detector_area_resol_mean 10.4167
_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'Incoatec microfocus sealed tube'
_diffrn_radiation_monochromator  'multilayer monochromator'
_diffrn_source_current           1.0
_diffrn_source_voltage           50.0
_diffrn_reflns_av_r_equivalents  0.0775
_diffrn_reflns_av_uneti/neti     0.0634
_diffrn_reflns_number            17354
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.894
_diffrn_reflns_theta_max         27.515
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_reflns_number_total             3887
_reflns_number_gt                3311
_reflns_threshold_expression     >2sigma(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.
;

#------------------------------------------------------------------------------#
#                            COMPUTER PROGRAMS USED                            #
#------------------------------------------------------------------------------#

_computing_data_collection       'SAINT (Bruker, 2014)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT (G. Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018_3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2016)'
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2019)'

#------------------------------------------------------------------------------#
#                            REFINEMENT INFORMATION                            #
#------------------------------------------------------------------------------#

_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     
'w=1/[σ²(Fo²)+(0.1403P)²+0.4782P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3887
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0920
_refine_ls_R_factor_gt           0.0829
_refine_ls_wR_factor_ref         0.2163
_refine_ls_wR_factor_gt          0.2065
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_restrained_S_all      1.156
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.179
_refine_diff_density_min         -1.014
_refine_diff_density_rms         0.143

#------------------------------------------------------------------------------#
#               ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS               #
#------------------------------------------------------------------------------#

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'

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
C1 C 1.2646(4) 0.51760(9) 0.86138(19) 0.0180(5) Uani 1 1 d . . . . .
H1A H 1.383303 0.499784 0.824175 0.022 Uiso 1 1 calc R U . . .
H1B H 1.223332 0.489225 0.916635 0.022 Uiso 1 1 calc R U . . .
C2 C 1.3483(4) 0.57438(10) 0.91895(19) 0.0217(5) Uani 1 1 d . . . . .
H2A H 1.472564 0.565048 0.974890 0.026 Uiso 1 1 calc R U . . .
H2B H 1.402382 0.601294 0.864638 0.026 Uiso 1 1 calc R U . . .
C3 C 1.1684(4) 0.60497(10) 0.97384(18) 0.0209(5) Uani 1 1 d . . . . .
H3A H 1.225088 0.642449 1.006917 0.025 Uiso 1 1 calc R U . . .
H3B H 1.123831 0.579737 1.033144 0.025 Uiso 1 1 calc R U . . .
C4 C 0.9700(4) 0.61723(10) 0.88986(18) 0.0204(5) Uani 1 1 d . . . . .
H4A H 0.851137 0.634708 0.927419 0.024 Uiso 1 1 calc R U . . .
H4B H 1.011080 0.645974 0.835189 0.024 Uiso 1 1 calc R U . . .
C5 C 0.8873(4) 0.56090(10) 0.83143(18) 0.0181(5) Uani 1 1 d . . . . .
H5A H 0.830662 0.534072 0.885129 0.022 Uiso 1 1 calc R U . . .
H5B H 0.764426 0.570638 0.774974 0.022 Uiso 1 1 calc R U . . .
C6 C 1.0660(4) 0.52947(9) 0.77706(17) 0.0148(5) Uani 1 1 d . . . . .
H6 H 1.111902 0.554744 0.717056 0.018 Uiso 1 1 calc R U . . .
N7 N 0.9729(3) 0.47454(8) 0.73006(15) 0.0163(4) Uani 1 1 d . . . . .
C8 C 1.0496(4) 0.45274(9) 0.64736(17) 0.0144(4) Uani 1 1 d . . . . .
N9 N 0.9664(3) 0.40171(8) 0.59234(14) 0.0155(4) Uani 1 1 d . . . . .
C10 C 1.0677(4) 0.38663(10) 0.49905(17) 0.0178(5) Uani 1 1 d . . . . .
C11 C 1.2343(4) 0.42239(11) 0.48283(19) 0.0216(5) Uani 1 1 d . . . . .
H11 H 1.321818 0.417804 0.424394 0.026 Uiso 1 1 calc R U . . .
C12 C 0.9797(4) 0.33659(10) 0.42947(19) 0.0233(5) Uani 1 1 d . . . . .
H12A H 1.070900 0.330648 0.369897 0.035 Uiso 1 1 calc R U . . .
H12B H 0.828999 0.345304 0.398525 0.035 Uiso 1 1 calc R U . . .
H12C H 0.981279 0.300854 0.474146 0.035 Uiso 1 1 calc R U . . .
N13 N 0.7909(3) 0.36789(8) 0.61377(15) 0.0164(4) Uani 1 1 d . . . . .
C14 C 0.6873(4) 0.37910(9) 0.69585(17) 0.0170(5) Uani 1 1 d . . . . .
H14 H 0.729678 0.411217 0.743021 0.020 Uiso 1 1 calc R U . . .
C15 C 0.5018(4) 0.34162(9) 0.71612(17) 0.0150(5) Uani 1 1 d . . . . .
C16 C 0.3891(4) 0.35521(10) 0.80536(18) 0.0191(5) Uani 1 1 d . . . . .
H16 H 0.433990 0.388269 0.849631 0.023 Uiso 1 1 calc R U . . .
C17 C 0.2148(4) 0.32203(10) 0.83088(18) 0.0208(5) Uani 1 1 d . . . . .
H17 H 0.138816 0.331754 0.891626 0.025 Uiso 1 1 calc R U . . .
C18 C 0.1535(4) 0.27383(9) 0.76501(19) 0.0195(5) Uani 1 1 d . . . . .
C19 C 0.2573(4) 0.25938(10) 0.67489(19) 0.0215(5) Uani 1 1 d . . . . .
H19 H 0.209491 0.226634 0.630432 0.026 Uiso 1 1 calc R U . . .
C20 C 0.4319(4) 0.29320(10) 0.65015(19) 0.0201(5) Uani 1 1 d . . . . .
H20 H 0.504952 0.283690 0.588296 0.024 Uiso 1 1 calc R U . . .
N21 N -0.0304(4) 0.23779(9) 0.79388(19) 0.0286(5) Uani 1 1 d . . . . .
O22 O -0.0801(4) 0.19420(10) 0.7383(2) 0.0534(7) Uani 1 1 d . . . . .
O23 O -0.1230(4) 0.25245(10) 0.87272(19) 0.0451(6) Uani 1 1 d . . . . .
S1 S 1.27352(9) 0.47827(2) 0.58039(4) 0.0194(2) Uani 1 1 d . . . . .



#------------------------------------------------------------------------------#
#                              MOLECULAR GEOMETRY                              #
#------------------------------------------------------------------------------#

_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
C1 C6 1.531(3) . ?
C1 C2 1.532(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.526(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.530(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.527(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.526(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N7 1.465(3) . ?
C6 H6 1.0000 . ?
N7 C8 1.268(3) . ?
C8 N9 1.409(3) . ?
C8 S1 1.778(2) . ?
N9 N13 1.374(3) . ?
N9 C10 1.407(3) . ?
C10 C11 1.340(3) . ?
C10 C12 1.487(3) . ?
C11 S1 1.744(2) . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
N13 C14 1.277(3) . ?
C14 C15 1.467(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.396(3) . ?
C15 C20 1.405(3) . ?
C16 C17 1.375(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.389(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.378(3) . ?
C18 N21 1.471(3) . ?
C19 C20 1.381(3) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
N21 O22 1.222(3) . ?
N21 O23 1.224(3) . ?

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 111.27(18) . . ?
C6 C1 H1A 109.4 . . ?
C2 C1 H1A 109.4 . . ?
C6 C1 H1B 109.4 . . ?
C2 C1 H1B 109.4 . . ?
H1A C1 H1B 108.0 . . ?
C3 C2 C1 111.49(19) . . ?
C3 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
C3 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 108.0 . . ?
C2 C3 C4 110.28(18) . . ?
C2 C3 H3A 109.6 . . ?
C4 C3 H3A 109.6 . . ?
C2 C3 H3B 109.6 . . ?
C4 C3 H3B 109.6 . . ?
H3A C3 H3B 108.1 . . ?
C5 C4 C3 111.14(18) . . ?
C5 C4 H4A 109.4 . . ?
C3 C4 H4A 109.4 . . ?
C5 C4 H4B 109.4 . . ?
C3 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C6 C5 C4 112.41(19) . . ?
C6 C5 H5A 109.1 . . ?
C4 C5 H5A 109.1 . . ?
C6 C5 H5B 109.1 . . ?
C4 C5 H5B 109.1 . . ?
H5A C5 H5B 107.9 . . ?
N7 C6 C5 107.69(18) . . ?
N7 C6 C1 111.18(17) . . ?
C5 C6 C1 110.13(17) . . ?
N7 C6 H6 109.3 . . ?
C5 C6 H6 109.3 . . ?
C1 C6 H6 109.3 . . ?
C8 N7 C6 119.02(19) . . ?
N7 C8 N9 124.0(2) . . ?
N7 C8 S1 128.32(17) . . ?
N9 C8 S1 107.72(15) . . ?
N13 N9 C10 116.66(18) . . ?
N13 N9 C8 128.23(17) . . ?
C10 N9 C8 114.93(18) . . ?
C11 C10 N9 112.9(2) . . ?
C11 C10 C12 127.8(2) . . ?
N9 C10 C12 119.3(2) . . ?
C10 C11 S1 112.85(17) . . ?
C10 C11 H11 123.6 . . ?
S1 C11 H11 123.6 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 N13 N9 120.78(18) . . ?
N13 C14 C15 118.97(19) . . ?
N13 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C16 C15 C20 118.7(2) . . ?
C16 C15 C14 117.95(19) . . ?
C20 C15 C14 123.4(2) . . ?
C17 C16 C15 121.7(2) . . ?
C17 C16 H16 119.1 . . ?
C15 C16 H16 119.1 . . ?
C16 C17 C18 117.9(2) . . ?
C16 C17 H17 121.1 . . ?
C18 C17 H17 121.1 . . ?
C19 C18 C17 122.4(2) . . ?
C19 C18 N21 119.9(2) . . ?
C17 C18 N21 117.7(2) . . ?
C18 C19 C20 119.1(2) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C19 C20 C15 120.2(2) . . ?
C19 C20 H20 119.9 . . ?
C15 C20 H20 119.9 . . ?
O22 N21 O23 123.6(2) . . ?
O22 N21 C18 117.9(2) . . ?
O23 N21 C18 118.5(2) . . ?
C11 S1 C8 91.50(11) . . ?

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
C6 C1 C2 C3 56.7(2) . . . . ?
C1 C2 C3 C4 -56.3(3) . . . . ?
C2 C3 C4 C5 55.4(3) . . . . ?
C3 C4 C5 C6 -55.7(2) . . . . ?
C4 C5 C6 N7 176.40(17) . . . . ?
C4 C5 C6 C1 55.0(2) . . . . ?
C2 C1 C6 N7 -174.33(18) . . . . ?
C2 C1 C6 C5 -55.1(2) . . . . ?
C5 C6 N7 C8 152.3(2) . . . . ?
C1 C6 N7 C8 -87.0(2) . . . . ?
C6 N7 C8 N9 -176.96(19) . . . . ?
C6 N7 C8 S1 3.5(3) . . . . ?
N7 C8 N9 N13 2.0(3) . . . . ?
S1 C8 N9 N13 -178.42(17) . . . . ?
N7 C8 N9 C10 176.9(2) . . . . ?
S1 C8 N9 C10 -3.5(2) . . . . ?
N13 N9 C10 C11 178.78(18) . . . . ?
C8 N9 C10 C11 3.3(3) . . . . ?
N13 N9 C10 C12 0.8(3) . . . . ?
C8 N9 C10 C12 -174.74(19) . . . . ?
N9 C10 C11 S1 -1.3(3) . . . . ?
C12 C10 C11 S1 176.47(19) . . . . ?
C10 N9 N13 C14 -178.90(19) . . . . ?
C8 N9 N13 C14 -4.1(3) . . . . ?
N9 N13 C14 C15 -179.59(17) . . . . ?
N13 C14 C15 C16 -179.1(2) . . . . ?
N13 C14 C15 C20 0.6(3) . . . . ?
C20 C15 C16 C17 1.0(3) . . . . ?
C14 C15 C16 C17 -179.3(2) . . . . ?
C15 C16 C17 C18 0.3(3) . . . . ?
C16 C17 C18 C19 -1.5(3) . . . . ?
C16 C17 C18 N21 178.9(2) . . . . ?
C17 C18 C19 C20 1.4(4) . . . . ?
N21 C18 C19 C20 -179.0(2) . . . . ?
C18 C19 C20 C15 -0.1(3) . . . . ?
C16 C15 C20 C19 -1.1(3) . . . . ?
C14 C15 C20 C19 179.2(2) . . . . ?
C19 C18 N21 O22 2.8(4) . . . . ?
C17 C18 N21 O22 -177.6(2) . . . . ?
C19 C18 N21 O23 -178.2(2) . . . . ?
C17 C18 N21 O23 1.4(3) . . . . ?
C10 C11 S1 C8 -0.59(19) . . . . ?
N7 C8 S1 C11 -178.1(2) . . . . ?
N9 C8 S1 C11 2.28(15) . . . . ?

#------------------------------------------------------------------------------#
#                                EMBEDDED FILES                                #
#------------------------------------------------------------------------------#
#                                                                              #

#...............................................................................
# .RES SHELXL file: job.res
#...............................................................................


