# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_FL2912_10ba
_database_code_depnum_ccdc_archive 'CCDC 1947178'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;CDIFX ISCR CNRS Univ Rennes
France
;
_audit_update_record             
;
2019-08-14 deposited with the CCDC.	2019-11-27 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 28 mai 2019                                              #
#------------------------------------------------------------------------------#


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


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H15 N5 O2, C H Cl3'
_chemical_formula_sum            'C19 H16 Cl3 N5 O2'
_chemical_formula_weight         452.72
_chemical_compound_source        'synthesis as described'

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


_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9499(10)
_cell_length_b                   9.8422(14)
_cell_length_c                   15.3854(19)
_cell_angle_alpha                87.986(5)
_cell_angle_beta                 87.262(5)
_cell_angle_gamma                69.331(5)
_cell_volume                     983.3(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150
_cell_measurement_reflns_used    9948
_cell_measurement_theta_min      2.5566
_cell_measurement_theta_max      27.5081
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.440
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.090
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             464
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.493
_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  0.818
_exptl_absorpt_correction_T_max  0.957

#------------------------------------------------------------------------------#
#                               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  0.0400
_diffrn_reflns_av_uneti/neti     0.0406
_diffrn_reflns_number            16645
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.212
_diffrn_reflns_theta_max         27.517
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_reflns_number_total             4451
_reflns_number_gt                4112
_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)+7.8458P] 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     'SHELXL-2018_3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.016(3)
_refine_ls_number_reflns         4451
_refine_ls_number_parameters     263
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0956
_refine_ls_R_factor_gt           0.0914
_refine_ls_wR_factor_ref         0.2255
_refine_ls_wR_factor_gt          0.2237
_refine_ls_goodness_of_fit_ref   1.198
_refine_ls_restrained_S_all      1.198
_refine_ls_shift/su_max          0.007
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         1.510
_refine_diff_density_min         -1.315
_refine_diff_density_rms         0.125

#------------------------------------------------------------------------------#
#               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'
O O 0.0106 0.0060 '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'
Cl Cl 0.1484 0.1585 '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 0.0983(7) 0.4698(5) 0.7172(3) 0.0170(9) Uani 1 1 d . . . . .
H1 H 0.147436 0.392828 0.677067 0.020 Uiso 1 1 calc R U . . .
C2 C 0.0555(8) 0.4426(5) 0.8033(3) 0.0226(10) Uani 1 1 d . . . . .
H2 H 0.073502 0.346783 0.823634 0.027 Uiso 1 1 calc R U . . .
C3 C -0.0143(8) 0.5584(6) 0.8591(3) 0.0253(10) Uani 1 1 d . . . . .
H3 H -0.042639 0.538457 0.918240 0.030 Uiso 1 1 calc R U . . .
N4 N -0.0450(7) 0.6970(5) 0.8358(3) 0.0244(9) Uani 1 1 d . . . . .
C5 C -0.0032(7) 0.7219(5) 0.7522(3) 0.0195(9) Uani 1 1 d . . . . .
H5 H -0.022928 0.818792 0.733647 0.023 Uiso 1 1 calc R U . . .
C6 C 0.0683(7) 0.6116(5) 0.6906(3) 0.0163(9) Uani 1 1 d . . . . .
C7 C 0.1157(6) 0.6486(5) 0.6017(3) 0.0155(8) Uani 1 1 d . . . . .
N8 N 0.0933(6) 0.7760(4) 0.5684(3) 0.0178(8) Uani 1 1 d . . . . .
C9 C 0.1720(7) 0.7475(4) 0.4827(3) 0.0160(9) Uani 1 1 d . . . . .
C10 C 0.1910(8) 0.8440(5) 0.4151(3) 0.0216(10) Uani 1 1 d . . . . .
H10 H 0.148493 0.945678 0.423664 0.026 Uiso 1 1 calc R U . . .
C11 C 0.2741(7) 0.7832(5) 0.3364(3) 0.0202(9) Uani 1 1 d . . . . .
H11 H 0.290630 0.844280 0.289665 0.024 Uiso 1 1 calc R U . . .
C12 C 0.3362(7) 0.6305(5) 0.3235(3) 0.0165(9) Uani 1 1 d . . . . .
C13 C 0.3212(7) 0.5333(4) 0.3908(3) 0.0145(8) Uani 1 1 d . . . . .
C14 C 0.2349(7) 0.6005(5) 0.4698(3) 0.0147(8) Uani 1 1 d . . . . .
O15 O 0.2004(5) 0.5342(3) 0.54582(19) 0.0142(6) Uani 1 1 d . . . . .
N16 N 0.4113(6) 0.5771(4) 0.2423(2) 0.0177(8) Uani 1 1 d . . . . .
C17 C 0.4707(7) 0.4367(5) 0.2325(3) 0.0174(9) Uani 1 1 d . . . . .
H17 H 0.520914 0.398332 0.176741 0.021 Uiso 1 1 calc R U . . .
C18 C 0.4633(6) 0.3372(5) 0.3032(3) 0.0141(8) Uani 1 1 d . . . . .
N19 N 0.3850(6) 0.3870(4) 0.3812(2) 0.0149(7) Uani 1 1 d . . . . .
N20 N 0.5416(6) 0.1901(4) 0.2932(2) 0.0178(8) Uani 1 1 d . . . . .
C21 C 0.5874(8) 0.1248(5) 0.2067(3) 0.0225(10) Uani 1 1 d . . . . .
H21A H 0.642256 0.184798 0.166874 0.027 Uiso 1 1 calc R U . . .
H21B H 0.459609 0.121708 0.182519 0.027 Uiso 1 1 calc R U . . .
C22 C 0.7439(9) -0.0275(5) 0.2134(4) 0.0304(12) Uani 1 1 d . . . . .
H22A H 0.767060 -0.073101 0.155609 0.036 Uiso 1 1 calc R U . . .
H22B H 0.876456 -0.023114 0.231348 0.036 Uiso 1 1 calc R U . . .
O23 O 0.6753(6) -0.1141(4) 0.2749(3) 0.0323(9) Uani 1 1 d . . . . .
C24 C 0.6556(8) -0.0529(5) 0.3587(3) 0.0247(10) Uani 1 1 d . . . . .
H24A H 0.790185 -0.049120 0.374319 0.030 Uiso 1 1 calc R U . . .
H24B H 0.616698 -0.116031 0.402232 0.030 Uiso 1 1 calc R U . . .
C25 C 0.4959(8) 0.0983(5) 0.3619(3) 0.0206(9) Uani 1 1 d . . . . .
H25A H 0.357782 0.093651 0.354196 0.025 Uiso 1 1 calc R U . . .
H25B H 0.495409 0.140715 0.419349 0.025 Uiso 1 1 calc R U . . .
C101 C 0.3665(9) 0.7789(6) 1.0710(3) 0.0277(11) Uani 1 1 d . . . . .
H101 H 0.395319 0.721100 1.126734 0.033 Uiso 1 1 calc R U . . .
Cl1 Cl 0.6019(2) 0.76172(18) 1.01574(10) 0.0397(4) Uani 1 1 d . . . . .
Cl2 Cl 0.2149(4) 0.7131(2) 1.00667(12) 0.0608(6) Uani 1 1 d . . . . .
Cl3 Cl 0.2300(2) 0.96253(16) 1.09474(10) 0.0367(4) 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 C2 1.381(7) . ?
C1 C6 1.387(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.382(7) . ?
C2 H2 0.9500 . ?
C3 N4 1.343(7) . ?
C3 H3 0.9500 . ?
N4 C5 1.338(6) . ?
C5 C6 1.403(6) . ?
C5 H5 0.9500 . ?
C6 C7 1.455(6) . ?
C7 N8 1.298(6) . ?
C7 O15 1.380(5) . ?
N8 C9 1.402(6) . ?
C9 C14 1.374(6) . ?
C9 C10 1.417(6) . ?
C10 C11 1.378(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.428(6) . ?
C11 H11 0.9500 . ?
C12 N16 1.378(6) . ?
C12 C13 1.410(6) . ?
C13 N19 1.359(5) . ?
C13 C14 1.408(6) . ?
C14 O15 1.372(5) . ?
N16 C17 1.307(6) . ?
C17 C18 1.449(6) . ?
C17 H17 0.9500 . ?
C18 N19 1.330(6) . ?
C18 N20 1.367(5) . ?
N20 C25 1.463(6) . ?
N20 C21 1.469(6) . ?
C21 C22 1.513(7) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 O23 1.427(6) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
O23 C24 1.422(6) . ?
C24 C25 1.511(6) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C101 Cl3 1.762(6) . ?
C101 Cl1 1.763(6) . ?
C101 Cl2 1.771(6) . ?
C101 H101 1.0000 . ?

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
C2 C1 C6 118.7(4) . . ?
C2 C1 H1 120.7 . . ?
C6 C1 H1 120.7 . . ?
C1 C2 C3 118.3(5) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 H2 120.9 . . ?
N4 C3 C2 124.7(5) . . ?
N4 C3 H3 117.6 . . ?
C2 C3 H3 117.6 . . ?
C5 N4 C3 116.4(4) . . ?
N4 C5 C6 123.1(4) . . ?
N4 C5 H5 118.4 . . ?
C6 C5 H5 118.4 . . ?
C1 C6 C5 118.8(4) . . ?
C1 C6 C7 122.0(4) . . ?
C5 C6 C7 119.2(4) . . ?
N8 C7 O15 115.3(4) . . ?
N8 C7 C6 128.1(4) . . ?
O15 C7 C6 116.5(4) . . ?
C7 N8 C9 104.0(4) . . ?
C14 C9 N8 108.8(4) . . ?
C14 C9 C10 121.2(4) . . ?
N8 C9 C10 130.0(4) . . ?
C11 C10 C9 116.7(4) . . ?
C11 C10 H10 121.6 . . ?
C9 C10 H10 121.6 . . ?
C10 C11 C12 121.6(4) . . ?
C10 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
N16 C12 C13 119.2(4) . . ?
N16 C12 C11 118.7(4) . . ?
C13 C12 C11 122.1(4) . . ?
N19 C13 C14 122.3(4) . . ?
N19 C13 C12 123.5(4) . . ?
C14 C13 C12 114.2(4) . . ?
O15 C14 C9 108.6(4) . . ?
O15 C14 C13 127.2(4) . . ?
C9 C14 C13 124.2(4) . . ?
C14 O15 C7 103.4(3) . . ?
C17 N16 C12 117.6(4) . . ?
N16 C17 C18 122.8(4) . . ?
N16 C17 H17 118.6 . . ?
C18 C17 H17 118.6 . . ?
N19 C18 N20 117.8(4) . . ?
N19 C18 C17 120.5(4) . . ?
N20 C18 C17 121.6(4) . . ?
C18 N19 C13 116.4(4) . . ?
C18 N20 C25 118.1(4) . . ?
C18 N20 C21 121.8(4) . . ?
C25 N20 C21 114.8(4) . . ?
N20 C21 C22 109.9(4) . . ?
N20 C21 H21A 109.7 . . ?
C22 C21 H21A 109.7 . . ?
N20 C21 H21B 109.7 . . ?
C22 C21 H21B 109.7 . . ?
H21A C21 H21B 108.2 . . ?
O23 C22 C21 111.0(4) . . ?
O23 C22 H22A 109.4 . . ?
C21 C22 H22A 109.4 . . ?
O23 C22 H22B 109.4 . . ?
C21 C22 H22B 109.4 . . ?
H22A C22 H22B 108.0 . . ?
C24 O23 C22 108.9(4) . . ?
O23 C24 C25 112.0(4) . . ?
O23 C24 H24A 109.2 . . ?
C25 C24 H24A 109.2 . . ?
O23 C24 H24B 109.2 . . ?
C25 C24 H24B 109.2 . . ?
H24A C24 H24B 107.9 . . ?
N20 C25 C24 110.0(4) . . ?
N20 C25 H25A 109.7 . . ?
C24 C25 H25A 109.7 . . ?
N20 C25 H25B 109.7 . . ?
C24 C25 H25B 109.7 . . ?
H25A C25 H25B 108.2 . . ?
Cl3 C101 Cl1 109.9(3) . . ?
Cl3 C101 Cl2 109.3(3) . . ?
Cl1 C101 Cl2 110.5(3) . . ?
Cl3 C101 H101 109.0 . . ?
Cl1 C101 H101 109.0 . . ?
Cl2 C101 H101 109.0 . . ?

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 -0.4(7) . . . . ?
C1 C2 C3 N4 0.3(8) . . . . ?
C2 C3 N4 C5 -0.2(8) . . . . ?
C3 N4 C5 C6 0.2(7) . . . . ?
C2 C1 C6 C5 0.4(7) . . . . ?
C2 C1 C6 C7 178.1(4) . . . . ?
N4 C5 C6 C1 -0.3(7) . . . . ?
N4 C5 C6 C7 -178.1(4) . . . . ?
C1 C6 C7 N8 179.4(4) . . . . ?
C5 C6 C7 N8 -2.9(7) . . . . ?
C1 C6 C7 O15 -2.6(6) . . . . ?
C5 C6 C7 O15 175.1(4) . . . . ?
O15 C7 N8 C9 -1.0(5) . . . . ?
C6 C7 N8 C9 177.1(4) . . . . ?
C7 N8 C9 C14 1.0(5) . . . . ?
C7 N8 C9 C10 -179.1(5) . . . . ?
C14 C9 C10 C11 0.3(7) . . . . ?
N8 C9 C10 C11 -179.5(5) . . . . ?
C9 C10 C11 C12 0.6(7) . . . . ?
C10 C11 C12 N16 177.7(4) . . . . ?
C10 C11 C12 C13 -1.8(7) . . . . ?
N16 C12 C13 N19 2.7(7) . . . . ?
C11 C12 C13 N19 -177.8(4) . . . . ?
N16 C12 C13 C14 -177.6(4) . . . . ?
C11 C12 C13 C14 1.8(6) . . . . ?
N8 C9 C14 O15 -0.7(5) . . . . ?
C10 C9 C14 O15 179.4(4) . . . . ?
N8 C9 C14 C13 179.7(4) . . . . ?
C10 C9 C14 C13 -0.2(7) . . . . ?
N19 C13 C14 O15 -0.7(7) . . . . ?
C12 C13 C14 O15 179.6(4) . . . . ?
N19 C13 C14 C9 178.8(4) . . . . ?
C12 C13 C14 C9 -0.9(6) . . . . ?
C9 C14 O15 C7 0.1(5) . . . . ?
C13 C14 O15 C7 179.7(4) . . . . ?
N8 C7 O15 C14 0.5(5) . . . . ?
C6 C7 O15 C14 -177.8(4) . . . . ?
C13 C12 N16 C17 -1.8(6) . . . . ?
C11 C12 N16 C17 178.7(4) . . . . ?
C12 N16 C17 C18 -1.0(7) . . . . ?
N16 C17 C18 N19 3.3(7) . . . . ?
N16 C17 C18 N20 -174.7(4) . . . . ?
N20 C18 N19 C13 175.7(4) . . . . ?
C17 C18 N19 C13 -2.3(6) . . . . ?
C14 C13 N19 C18 179.9(4) . . . . ?
C12 C13 N19 C18 -0.5(6) . . . . ?
N19 C18 N20 C25 12.7(6) . . . . ?
C17 C18 N20 C25 -169.3(4) . . . . ?
N19 C18 N20 C21 165.7(4) . . . . ?
C17 C18 N20 C21 -16.3(7) . . . . ?
C18 N20 C21 C22 157.7(4) . . . . ?
C25 N20 C21 C22 -48.5(6) . . . . ?
N20 C21 C22 O23 55.4(6) . . . . ?
C21 C22 O23 C24 -62.9(6) . . . . ?
C22 O23 C24 C25 62.5(5) . . . . ?
C18 N20 C25 C24 -157.5(4) . . . . ?
C21 N20 C25 C24 47.7(6) . . . . ?
O23 C24 C25 N20 -54.2(5) . . . . ?

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

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


####################################################################### 
# 
# 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_FL316
_database_code_depnum_ccdc_archive 'CCDC 1964834'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;Institut des Sciences Chimiques de Rennes
France
;
_audit_update_record             
;
2019-11-11 deposited with the CCDC.	2019-11-27 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 06 novembre 2019                                         #
#------------------------------------------------------------------------------#


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


_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C18 H18 N6 O S'
_chemical_formula_sum            'C18 H18 N6 O S'
_chemical_formula_weight         366.44
_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                   15.2934(7)
_cell_length_b                   5.9374(3)
_cell_length_c                   19.2117(11)
_cell_angle_alpha                90
_cell_angle_beta                 101.042(2)
_cell_angle_gamma                90
_cell_volume                     1712.19(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    150
_cell_measurement_reflns_used    6507
_cell_measurement_theta_min      3.2653
_cell_measurement_theta_max      27.5199
_cell_measurement_wavelength     0.71073


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

_diffrn_orient_matrix_UB_11      0.0189322
_diffrn_orient_matrix_UB_21      -0.0037284
_diffrn_orient_matrix_UB_31      -0.0637761
_diffrn_orient_matrix_UB_12      -0.1176723
_diffrn_orient_matrix_UB_22      0.1131247
_diffrn_orient_matrix_UB_32      -0.0415450
_diffrn_orient_matrix_UB_13      0.0370676
_diffrn_orient_matrix_UB_23      0.0378855
_diffrn_orient_matrix_UB_33      -0.0018303


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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.540
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.090
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.422
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             768
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.210
_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  0.822
_exptl_absorpt_correction_T_max  0.981

#------------------------------------------------------------------------------#
#                               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  0.0409
_diffrn_reflns_av_uneti/neti     0.0362
_diffrn_reflns_number            13845
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.265
_diffrn_reflns_theta_max         27.557
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.984
_reflns_number_total             3900
_reflns_number_gt                3215
_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)+(0.0442P)²+1.0595P] 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         3900
_refine_ls_number_parameters     236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0506
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.1021
_refine_ls_wR_factor_gt          0.0948
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_restrained_S_all      1.033
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.053

#------------------------------------------------------------------------------#
#               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 0.18532(11) 1.1653(3) 0.70713(8) 0.0216(3) Uani 1 1 d . . . . .
H1A H 0.209024 1.187893 0.758325 0.026 Uiso 1 1 calc R U . . .
H1B H 0.160622 1.010975 0.700637 0.026 Uiso 1 1 calc R U . . .
C2 C 0.26050(10) 1.1896(3) 0.66629(8) 0.0204(3) Uani 1 1 d . . . . .
H2A H 0.284901 1.344283 0.672569 0.024 Uiso 1 1 calc R U . . .
H2B H 0.308917 1.083314 0.685736 0.024 Uiso 1 1 calc R U . . .
N3 N 0.23023(9) 1.1447(2) 0.59059(7) 0.0206(3) Uani 1 1 d . . . . .
C4 C 0.16394(11) 1.3042(3) 0.55439(8) 0.0220(3) Uani 1 1 d . . . . .
H4A H 0.150187 1.268784 0.503101 0.026 Uiso 1 1 calc R U . . .
H4B H 0.188783 1.458591 0.559981 0.026 Uiso 1 1 calc R U . . .
C5 C 0.07860(11) 1.2950(3) 0.58409(9) 0.0255(4) Uani 1 1 d . . . . .
H5A H 0.053211 1.141373 0.577494 0.031 Uiso 1 1 calc R U . . .
H5B H 0.034582 1.400807 0.557283 0.031 Uiso 1 1 calc R U . . .
C6 C 0.26290(10) 0.9653(3) 0.55916(8) 0.0164(3) Uani 1 1 d . . . . .
C7 C 0.23493(11) 0.9231(3) 0.48365(8) 0.0198(3) Uani 1 1 d . . . . .
H7 H 0.191907 1.020281 0.456757 0.024 Uiso 1 1 calc R U . . .
N8 N 0.26642(9) 0.7576(2) 0.45130(7) 0.0199(3) Uani 1 1 d . . . . .
C9 C 0.32844(10) 0.6185(3) 0.49088(8) 0.0166(3) Uani 1 1 d . . . . .
C10 C 0.36257(11) 0.4352(3) 0.45710(8) 0.0205(3) Uani 1 1 d . . . . .
H10 H 0.344567 0.417862 0.407256 0.025 Uiso 1 1 calc R U . . .
C11 C 0.42079(11) 0.2818(3) 0.49405(8) 0.0205(3) Uani 1 1 d . . . . .
H11 H 0.442615 0.157808 0.471186 0.025 Uiso 1 1 calc R U . . .
C12 C 0.44659(10) 0.3178(3) 0.56785(8) 0.0174(3) Uani 1 1 d . . . . .
N13 N 0.50326(9) 0.1913(2) 0.61928(7) 0.0191(3) Uani 1 1 d . . . . .
C14 C 0.50204(10) 0.2985(3) 0.67807(8) 0.0165(3) Uani 1 1 d . . . . .
O15 O 0.45050(7) 0.49027(18) 0.67191(5) 0.0163(2) Uani 1 1 d . . . . .
C16 C 0.41480(10) 0.4991(3) 0.60028(7) 0.0159(3) Uani 1 1 d . . . . .
C17 C 0.35413(9) 0.6580(3) 0.56494(7) 0.0151(3) Uani 1 1 d . . . . .
N18 N 0.32098(8) 0.8299(2) 0.59904(6) 0.0161(3) Uani 1 1 d . . . . .
C19 C 0.54478(10) 0.2447(3) 0.74983(8) 0.0177(3) Uani 1 1 d . . . . .
C20 C 0.54166(10) 0.3576(3) 0.81205(8) 0.0209(3) Uani 1 1 d . . . . .
H20 H 0.511996 0.496865 0.814964 0.025 Uiso 1 1 calc R U . . .
N21 N 0.58737(9) 0.2407(3) 0.86905(7) 0.0248(3) Uani 1 1 d . . . . .
C22 C 0.61763(11) 0.0597(3) 0.84135(8) 0.0229(3) Uani 1 1 d . . . . .
H22 H 0.652346 -0.053213 0.868801 0.027 Uiso 1 1 calc R U . . .
N23 N 0.59400(8) 0.0521(2) 0.76977(7) 0.0184(3) Uani 1 1 d . . . . .
C24 C 0.62197(11) -0.1216(3) 0.72435(9) 0.0223(3) Uani 1 1 d . . . . .
H24A H 0.574443 -0.144765 0.682099 0.027 Uiso 1 1 calc R U . . .
H24B H 0.631277 -0.265692 0.750669 0.027 Uiso 1 1 calc R U . . .
C25 C 0.70735(12) -0.0538(3) 0.70100(9) 0.0265(4) Uani 1 1 d . . . . .
H25A H 0.697238 0.084517 0.672764 0.040 Uiso 1 1 calc R U . . .
H25B H 0.726035 -0.174519 0.672277 0.040 Uiso 1 1 calc R U . . .
H25C H 0.754021 -0.027476 0.742844 0.040 Uiso 1 1 calc R U . . .
S1 S 0.09750(3) 1.36717(8) 0.67752(2) 0.02504(12) 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 C2 1.518(2) . ?
C1 S1 1.8086(17) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 N3 1.4637(18) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
N3 C6 1.366(2) . ?
N3 C4 1.462(2) . ?
C4 C5 1.522(2) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 S1 1.8140(17) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 N18 1.3270(19) . ?
C6 C7 1.453(2) . ?
C7 N8 1.303(2) . ?
C7 H7 0.9500 . ?
N8 C9 1.372(2) . ?
C9 C10 1.417(2) . ?
C9 C17 1.4211(19) . ?
C10 C11 1.372(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.413(2) . ?
C11 H11 0.9500 . ?
C12 C16 1.378(2) . ?
C12 N13 1.4013(19) . ?
N13 C14 1.300(2) . ?
C14 O15 1.3768(18) . ?
C14 C19 1.444(2) . ?
O15 C16 1.3810(16) . ?
C16 C17 1.404(2) . ?
C17 N18 1.362(2) . ?
C19 C20 1.379(2) . ?
C19 N23 1.382(2) . ?
C20 N21 1.370(2) . ?
C20 H20 0.9500 . ?
N21 C22 1.321(2) . ?
C22 N23 1.354(2) . ?
C22 H22 0.9500 . ?
N23 C24 1.467(2) . ?
C24 C25 1.514(2) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?

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
C2 C1 S1 111.40(11) . . ?
C2 C1 H1A 109.3 . . ?
S1 C1 H1A 109.3 . . ?
C2 C1 H1B 109.3 . . ?
S1 C1 H1B 109.3 . . ?
H1A C1 H1B 108.0 . . ?
N3 C2 C1 111.69(13) . . ?
N3 C2 H2A 109.3 . . ?
C1 C2 H2A 109.3 . . ?
N3 C2 H2B 109.3 . . ?
C1 C2 H2B 109.3 . . ?
H2A C2 H2B 107.9 . . ?
C6 N3 C4 125.03(13) . . ?
C6 N3 C2 120.57(12) . . ?
C4 N3 C2 114.40(12) . . ?
N3 C4 C5 111.37(13) . . ?
N3 C4 H4A 109.4 . . ?
C5 C4 H4A 109.4 . . ?
N3 C4 H4B 109.4 . . ?
C5 C4 H4B 109.4 . . ?
H4A C4 H4B 108.0 . . ?
C4 C5 S1 112.14(11) . . ?
C4 C5 H5A 109.2 . . ?
S1 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
S1 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
N18 C6 N3 118.56(13) . . ?
N18 C6 C7 120.57(14) . . ?
N3 C6 C7 120.86(13) . . ?
N8 C7 C6 122.74(14) . . ?
N8 C7 H7 118.6 . . ?
C6 C7 H7 118.6 . . ?
C7 N8 C9 117.95(13) . . ?
N8 C9 C10 118.98(13) . . ?
N8 C9 C17 118.99(14) . . ?
C10 C9 C17 121.99(14) . . ?
C11 C10 C9 122.15(14) . . ?
C11 C10 H10 118.9 . . ?
C9 C10 H10 118.9 . . ?
C10 C11 C12 116.57(14) . . ?
C10 C11 H11 121.7 . . ?
C12 C11 H11 121.7 . . ?
C16 C12 N13 108.90(13) . . ?
C16 C12 C11 121.12(14) . . ?
N13 C12 C11 129.98(14) . . ?
C14 N13 C12 103.91(13) . . ?
N13 C14 O15 115.70(13) . . ?
N13 C14 C19 129.95(14) . . ?
O15 C14 C19 114.33(13) . . ?
C14 O15 C16 103.15(11) . . ?
C12 C16 O15 108.34(12) . . ?
C12 C16 C17 124.34(13) . . ?
O15 C16 C17 127.29(13) . . ?
N18 C17 C16 122.93(13) . . ?
N18 C17 C9 123.24(13) . . ?
C16 C17 C9 113.81(13) . . ?
C6 N18 C17 116.46(12) . . ?
C20 C19 N23 105.63(13) . . ?
C20 C19 C14 129.45(14) . . ?
N23 C19 C14 124.79(14) . . ?
N21 C20 C19 110.45(14) . . ?
N21 C20 H20 124.8 . . ?
C19 C20 H20 124.8 . . ?
C22 N21 C20 104.75(13) . . ?
N21 C22 N23 112.99(14) . . ?
N21 C22 H22 123.5 . . ?
N23 C22 H22 123.5 . . ?
C22 N23 C19 106.19(13) . . ?
C22 N23 C24 125.20(13) . . ?
C19 N23 C24 128.48(13) . . ?
N23 C24 C25 110.83(13) . . ?
N23 C24 H24A 109.5 . . ?
C25 C24 H24A 109.5 . . ?
N23 C24 H24B 109.5 . . ?
C25 C24 H24B 109.5 . . ?
H24A C24 H24B 108.1 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C1 S1 C5 97.05(8) . . ?

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
S1 C1 C2 N3 -62.38(16) . . . . ?
C1 C2 N3 C6 -115.48(16) . . . . ?
C1 C2 N3 C4 64.08(18) . . . . ?
C6 N3 C4 C5 116.58(17) . . . . ?
C2 N3 C4 C5 -62.96(18) . . . . ?
N3 C4 C5 S1 60.90(17) . . . . ?
C4 N3 C6 N18 -177.94(14) . . . . ?
C2 N3 C6 N18 1.6(2) . . . . ?
C4 N3 C6 C7 2.2(2) . . . . ?
C2 N3 C6 C7 -178.34(14) . . . . ?
N18 C6 C7 N8 -1.9(2) . . . . ?
N3 C6 C7 N8 178.01(15) . . . . ?
C6 C7 N8 C9 0.1(2) . . . . ?
C7 N8 C9 C10 178.98(15) . . . . ?
C7 N8 C9 C17 1.2(2) . . . . ?
N8 C9 C10 C11 -176.17(15) . . . . ?
C17 C9 C10 C11 1.6(2) . . . . ?
C9 C10 C11 C12 -1.1(2) . . . . ?
C10 C11 C12 C16 -0.4(2) . . . . ?
C10 C11 C12 N13 179.09(16) . . . . ?
C16 C12 N13 C14 0.49(17) . . . . ?
C11 C12 N13 C14 -179.01(16) . . . . ?
C12 N13 C14 O15 -0.89(17) . . . . ?
C12 N13 C14 C19 177.28(15) . . . . ?
N13 C14 O15 C16 0.91(17) . . . . ?
C19 C14 O15 C16 -177.55(12) . . . . ?
N13 C12 C16 O15 0.03(17) . . . . ?
C11 C12 C16 O15 179.59(13) . . . . ?
N13 C12 C16 C17 -178.07(14) . . . . ?
C11 C12 C16 C17 1.5(2) . . . . ?
C14 O15 C16 C12 -0.52(15) . . . . ?
C14 O15 C16 C17 177.52(15) . . . . ?
C12 C16 C17 N18 177.07(14) . . . . ?
O15 C16 C17 N18 -0.7(2) . . . . ?
C12 C16 C17 C9 -1.0(2) . . . . ?
O15 C16 C17 C9 -178.75(13) . . . . ?
N8 C9 C17 N18 -0.8(2) . . . . ?
C10 C9 C17 N18 -178.55(14) . . . . ?
N8 C9 C17 C16 177.25(14) . . . . ?
C10 C9 C17 C16 -0.5(2) . . . . ?
N3 C6 N18 C17 -177.73(13) . . . . ?
C7 C6 N18 C17 2.2(2) . . . . ?
C16 C17 N18 C6 -178.81(14) . . . . ?
C9 C17 N18 C6 -0.9(2) . . . . ?
N13 C14 C19 C20 -178.63(16) . . . . ?
O15 C14 C19 C20 -0.4(2) . . . . ?
N13 C14 C19 N23 -3.4(3) . . . . ?
O15 C14 C19 N23 174.79(13) . . . . ?
N23 C19 C20 N21 0.12(18) . . . . ?
C14 C19 C20 N21 176.06(15) . . . . ?
C19 C20 N21 C22 0.05(18) . . . . ?
C20 N21 C22 N23 -0.21(18) . . . . ?
N21 C22 N23 C19 0.28(18) . . . . ?
N21 C22 N23 C24 176.46(14) . . . . ?
C20 C19 N23 C22 -0.23(17) . . . . ?
C14 C19 N23 C22 -176.41(15) . . . . ?
C20 C19 N23 C24 -176.24(14) . . . . ?
C14 C19 N23 C24 7.6(2) . . . . ?
C22 N23 C24 C25 -90.71(18) . . . . ?
C19 N23 C24 C25 84.60(19) . . . . ?
C2 C1 S1 C5 54.16(13) . . . . ?
C4 C5 S1 C1 -53.80(13) . . . . ?

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
_geom_hbond_publ_flag
#
# Hydrogen bonding scheme
# -----------------------
#
# D       H       A       D-H         H...A       D...A      D-H...A   symm publ
# ------------------------------------------------------------------------------
C4 H4A N21 0.99 2.57 3.539(2) 165.7 4_575 yes
C7 H7 N21 0.95 2.53 3.467(2) 171.2 4_575 yes
C20 H20 S1 0.95 2.78 3.7265(17) 171.6 2_546 yes
C22 H22 N8 0.95 2.44 3.369(2) 164.7 4_666 yes
C24 H24A N13 0.99 2.47 3.069(2) 118.3 . yes

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

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


