# Supplementary Information (SI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 2026

####################################################################### 
# 
# 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_JTL1
_database_code_depnum_ccdc_archive 'CCDC 2480983'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;University of Rennes
France
;
_audit_update_record             
;
2025-08-17 deposited with the CCDC.	2026-04-17 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 26 novembre 2024                                         #
#------------------------------------------------------------------------------#


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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H10 N4'
_chemical_formula_sum            'C13 H10 N4'
_chemical_formula_weight         222.25
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_IT_number           61
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   7.8672(8)
_cell_length_b                   10.8446(10)
_cell_length_c                   25.307(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2159.2(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9874
_cell_measurement_theta_min      3.0489
_cell_measurement_theta_max      27.4601
_cell_measurement_wavelength     0.710730


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

_diffrn_orient_matrix_UB_11      -0.0475289
_diffrn_orient_matrix_UB_21      -0.0967210
_diffrn_orient_matrix_UB_31      -0.0674011
_diffrn_orient_matrix_UB_12      0.0096916
_diffrn_orient_matrix_UB_22      -0.0555867
_diffrn_orient_matrix_UB_32      0.0729330
_diffrn_orient_matrix_UB_13      -0.0364115
_diffrn_orient_matrix_UB_23      0.0094839
_diffrn_orient_matrix_UB_33      0.0120667


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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             928
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.087
_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  0.913
_exptl_absorpt_correction_T_max  0.984

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

# Software                   : BIS V6.2.15/2021-03-15 && APEX4 2022.10-0       #
# Total number of scans:        5                                              #
#                                                                              #
# ....[fast scans included]:                                                   #
#    . Total number of frames :      774                                       #
#    . Total length of scans  :   649.80 (deg.)                                #
#    . Mean rotation speed    :     8.57 sec./deg.                             #
#    . Total exposition time  :      1 h 21 min. [81 min.]                     #
#                                                                              #
#                                                                              #
# ....[fast scans excluded]:                                                   #
#    . Total number of frames :      414                                       #
#    . Total length of scans  :   289.80 (deg.)                                #
#    . Mean rotation speed    :    14.29 sec./deg.                             #
#    . Total exposition time  :      1 h  9 min. [69 min.]                     #
#                                                                              #
#                                                                              #
#    Scan  Time(s) Width DX(mm) Frames Range 2Theta  Omega    Phi    Chi  T(K) #
#..............................................................................#
#                                                                              #
#  1 Fast     2.0  1.00    34.0   180  180.0    0.0    0.0    0.0   54.7 150.0 #
#  2 Fast@    2.0  1.00    34.0   180  180.0    0.0    0.0  180.0   54.7 150.0 #
#  3 Omega   10.0  0.70    34.0   138   96.6    0.1    3.1  144.0  -44.5 150.0 #
#  4 Omega   10.0  0.70    34.0   138   96.6    0.1    3.1    0.0  -44.5 150.0 #
#  5 Omega   10.0  0.70    34.0   138   96.6    0.1    3.1  216.0  -44.5 150.0 #
#                                                                              #
#  @: attenuated beam                                                          #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 CMOS-PHOTON70
_diffrn_detector_area_resol_mean 7.39
_diffrn_ambient_temperature      150(2)
_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           1.00
_diffrn_source_voltage           50.00
_diffrn_source_power             50.0
_diffrn_reflns_av_uneti/neti     0.0155
_diffrn_reflns_av_r_equivalents  0.0312
_diffrn_reflns_number            23856
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.049
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_reflns_number_total             2470
_reflns_number_gt                2317
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.
;

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

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019_2 (Sheldrick, 2019)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2024)'

#------------------------------------------------------------------------------#
#                            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)+(0.0519P)²+0.9283P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2470
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0429
_refine_ls_R_factor_gt           0.0405
_refine_ls_wR_factor_ref         0.1050
_refine_ls_wR_factor_gt          0.1031
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.048

#------------------------------------------------------------------------------#
#               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'

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 0.48071(15) 0.56200(11) 0.69591(5) 0.0251(3) Uani 1 1 d . . . . .
H1 H 0.506157 0.647306 0.692683 0.030 Uiso 1 1 calc R U . . .
C2 C 0.39039(16) 0.51976(12) 0.73924(5) 0.0292(3) Uani 1 1 d . . . . .
H2 H 0.354710 0.576240 0.765708 0.035 Uiso 1 1 calc R U . . .
C3 C 0.35173(17) 0.39571(13) 0.74426(5) 0.0319(3) Uani 1 1 d . . . . .
H3 H 0.288708 0.367254 0.773869 0.038 Uiso 1 1 calc R U . . .
C4 C 0.40550(16) 0.31321(12) 0.70583(5) 0.0298(3) Uani 1 1 d . . . . .
H4 H 0.379315 0.228064 0.709231 0.036 Uiso 1 1 calc R U . . .
C5 C 0.49716(15) 0.35433(11) 0.66253(5) 0.0246(3) Uani 1 1 d . . . . .
H5 H 0.534691 0.297148 0.636602 0.030 Uiso 1 1 calc R U . . .
C6 C 0.53459(14) 0.47949(10) 0.65687(4) 0.0211(2) Uani 1 1 d . . . . .
C7 C 0.62473(14) 0.52376(10) 0.60984(4) 0.0207(2) Uani 1 1 d . . . . .
C8 C 0.65620(14) 0.46433(10) 0.56309(4) 0.0218(2) Uani 1 1 d . . . . .
H8 H 0.627866 0.381906 0.553924 0.026 Uiso 1 1 calc R U . . .
N9 N 0.73639(12) 0.54887(9) 0.53297(4) 0.0212(2) Uani 1 1 d . . . . .
N10 N 0.75601(14) 0.65635(9) 0.55937(4) 0.0275(2) Uani 1 1 d . . . . .
N11 N 0.68773(14) 0.64090(9) 0.60614(4) 0.0269(2) Uani 1 1 d . . . . .
C12 C 0.79587(14) 0.53450(10) 0.48005(4) 0.0204(2) Uani 1 1 d . . . . .
C13 C 0.88643(15) 0.62767(11) 0.45542(5) 0.0253(3) Uani 1 1 d . . . . .
H13 H 0.910460 0.703315 0.472822 0.030 Uiso 1 1 calc R U . . .
C14 C 0.94028(16) 0.60534(11) 0.40426(5) 0.0269(3) Uani 1 1 d . . . . .
H14 H 1.003473 0.666019 0.385625 0.032 Uiso 1 1 calc R U . . .
C15 C 0.90152(15) 0.49420(12) 0.38046(5) 0.0264(3) Uani 1 1 d . . . . .
H15 H 0.937105 0.477185 0.345336 0.032 Uiso 1 1 calc R U . . .
C16 C 0.80951(16) 0.40822(11) 0.40907(5) 0.0270(3) Uani 1 1 d . . . . .
H16 H 0.782749 0.331941 0.392591 0.032 Uiso 1 1 calc R U . . .
N17 N 0.75629(13) 0.42669(9) 0.45860(4) 0.0239(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 C2 1.3847(18) . ?
C1 C6 1.3989(16) . ?
C1 H1 0.9500 . ?
C2 C3 1.3851(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.3875(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.3855(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.3962(16) . ?
C5 H5 0.9500 . ?
C6 C7 1.4663(16) . ?
C7 N11 1.3668(15) . ?
C7 C8 1.3697(15) . ?
C8 N9 1.3490(14) . ?
C8 H8 0.9500 . ?
N9 N10 1.3523(13) . ?
N9 C12 1.4272(14) . ?
N10 N11 1.3106(14) . ?
C12 N17 1.3260(15) . ?
C12 C13 1.3845(16) . ?
C13 C14 1.3838(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.3814(17) . ?
C14 H14 0.9500 . ?
C15 C16 1.3848(17) . ?
C15 H15 0.9500 . ?
C16 N17 1.3368(15) . ?
C16 H16 0.9500 . ?

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 120.22(11) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C3 C2 C1 120.44(11) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.68(12) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 120.36(12) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.26(11) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 119.04(11) . . ?
C5 C6 C7 120.24(10) . . ?
C1 C6 C7 120.70(11) . . ?
N11 C7 C8 108.22(10) . . ?
N11 C7 C6 122.36(10) . . ?
C8 C7 C6 129.38(11) . . ?
N9 C8 C7 104.65(10) . . ?
N9 C8 H8 127.7 . . ?
C7 C8 H8 127.7 . . ?
C8 N9 N10 111.10(9) . . ?
C8 N9 C12 127.55(10) . . ?
N10 N9 C12 121.36(9) . . ?
N11 N10 N9 106.82(9) . . ?
N10 N11 C7 109.22(9) . . ?
N17 C12 C13 125.45(11) . . ?
N17 C12 N9 113.79(10) . . ?
C13 C12 N9 120.76(10) . . ?
C14 C13 C12 116.81(11) . . ?
C14 C13 H13 121.6 . . ?
C12 C13 H13 121.6 . . ?
C15 C14 C13 119.54(11) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C14 C15 C16 118.35(11) . . ?
C14 C15 H15 120.8 . . ?
C16 C15 H15 120.8 . . ?
N17 C16 C15 123.58(11) . . ?
N17 C16 H16 118.2 . . ?
C15 C16 H16 118.2 . . ?
C12 N17 C16 116.26(10) . . ?

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 -0.34(18) . . . . ?
C1 C2 C3 C4 0.66(19) . . . . ?
C2 C3 C4 C5 -0.1(2) . . . . ?
C3 C4 C5 C6 -0.74(19) . . . . ?
C4 C5 C6 C1 1.06(17) . . . . ?
C4 C5 C6 C7 -177.17(11) . . . . ?
C2 C1 C6 C5 -0.52(17) . . . . ?
C2 C1 C6 C7 177.70(11) . . . . ?
C5 C6 C7 N11 -169.45(11) . . . . ?
C1 C6 C7 N11 12.35(17) . . . . ?
C5 C6 C7 C8 13.21(18) . . . . ?
C1 C6 C7 C8 -164.98(11) . . . . ?
N11 C7 C8 N9 -0.34(13) . . . . ?
C6 C7 C8 N9 177.29(11) . . . . ?
C7 C8 N9 N10 0.43(13) . . . . ?
C7 C8 N9 C12 -179.31(10) . . . . ?
C8 N9 N10 N11 -0.35(13) . . . . ?
C12 N9 N10 N11 179.40(10) . . . . ?
N9 N10 N11 C7 0.13(13) . . . . ?
C8 C7 N11 N10 0.14(13) . . . . ?
C6 C7 N11 N10 -177.70(10) . . . . ?
C8 N9 C12 N17 4.17(16) . . . . ?
N10 N9 C12 N17 -175.54(10) . . . . ?
C8 N9 C12 C13 -175.65(11) . . . . ?
N10 N9 C12 C13 4.63(16) . . . . ?
N17 C12 C13 C14 -0.32(18) . . . . ?
N9 C12 C13 C14 179.48(10) . . . . ?
C12 C13 C14 C15 0.36(17) . . . . ?
C13 C14 C15 C16 -0.15(18) . . . . ?
C14 C15 C16 N17 -0.16(19) . . . . ?
C13 C12 N17 C16 0.03(18) . . . . ?
N9 C12 N17 C16 -179.78(10) . . . . ?
C15 C16 N17 C12 0.22(18) . . . . ?

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

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



# ............... End of .RES file ........................................... #
#------------------------------------------------------------------------------#

#...............................................................................
# .HKL SHELXL file: job.hkl
#...............................................................................



# ............... End of .HKL file ........................................... #
#------------------------------------------------------------------------------#

#------------------------------------------------------------------------------#
#===END OF CIF FILE FOR JTL1                                                   #
#------------------------------------------------------------------------------#
#                                                                              #
################################################################################
####################################################################### 
# 
# 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_VD210
_database_code_depnum_ccdc_archive 'CCDC 2480985'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;University of Rennes
France
;
_audit_update_record             
;
2025-08-17 deposited with the CCDC.	2026-04-17 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 18 janvier 2024                                          #
#------------------------------------------------------------------------------#


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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C13 H9 N O'
_chemical_formula_sum            'C13 H9 N O'
_chemical_formula_weight         195.21
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
_space_group_IT_number           15
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   9.9855(11)
_cell_length_b                   10.2909(10)
_cell_length_c                   17.6733(19)
_cell_angle_alpha                90
_cell_angle_beta                 98.485(4)
_cell_angle_gamma                90
_cell_volume                     1796.2(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9916
_cell_measurement_theta_min      2.3303
_cell_measurement_theta_max      27.4884
_cell_measurement_wavelength     0.710730


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

_diffrn_orient_matrix_UB_11      -0.0774135
_diffrn_orient_matrix_UB_21      -0.0648131
_diffrn_orient_matrix_UB_31      0.0076558
_diffrn_orient_matrix_UB_12      0.0212351
_diffrn_orient_matrix_UB_22      -0.0142905
_diffrn_orient_matrix_UB_32      0.0937420
_diffrn_orient_matrix_UB_13      -0.0407643
_diffrn_orient_matrix_UB_23      0.0372647
_diffrn_orient_matrix_UB_33      0.0149150


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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.100
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             816
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.092
_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  0.930
_exptl_absorpt_correction_T_max  0.991

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

# Software                   : BIS V6.2.15/2021-03-15 && APEX4 2022.10-0       #
# Total number of scans:        7                                              #
#                                                                              #
# ....[fast scans included]:                                                   #
#    . Total number of frames :     1856                                       #
#    . Total length of scans  :  1108.00 (deg.)                                #
#    . Mean rotation speed    :    16.51 sec./deg.                             #
#    . Total exposition time  :      4 h 21 min. [261 min.]                    #
#                                                                              #
#                                                                              #
# ....[fast scans excluded]:                                                   #
#    . Total number of frames :     1496                                       #
#    . Total length of scans  :   748.00 (deg.)                                #
#    . Mean rotation speed    :    20.00 sec./deg.                             #
#    . Total exposition time  :      4 h  9 min. [249 min.]                    #
#                                                                              #
#                                                                              #
#    Scan  Time(s) Width DX(mm) Frames Range 2Theta  Omega    Phi    Chi  T(K) #
#..............................................................................#
#                                                                              #
#  1 Fast     2.0  1.00    34.0   180  180.0    0.0    0.0    0.0   54.7 150.0 #
#  2 Fast@    2.0  1.00    34.0   180  180.0    0.0    0.0  180.0   54.7 150.0 #
#  3 Omega   10.0  0.50    34.0   194   97.0    0.1    2.7  144.0  -44.5 150.0 #
#  4 Omega   10.0  0.50    34.0   194   97.0    0.1    2.7    0.0  -44.5 150.0 #
#  5 Omega   10.0  0.50    34.0   194   97.0    0.1    2.7  216.0  -44.5 150.0 #
#  6 Phi     10.0  0.50    34.0   720  360.0    0.1    2.4    0.0  -44.5 150.0 #
#  7 Omega   10.0  0.50    34.0   194   97.0    0.1    2.7   72.0  -44.5 150.0 #
#                                                                              #
#  @: attenuated beam                                                          #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 CMOS-PHOTON70
_diffrn_detector_area_resol_mean 7.39
_diffrn_ambient_temperature      150(2)
_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           1.00
_diffrn_source_voltage           50.00
_diffrn_source_power             50.0
_diffrn_reflns_av_uneti/neti     0.0255
_diffrn_reflns_av_r_equivalents  0.0451
_diffrn_reflns_number            23509
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.330
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.997
_reflns_number_total             2055
_reflns_number_gt                1991
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.
;

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

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019_2 (Sheldrick, 2019)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2023)'

#------------------------------------------------------------------------------#
#                            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)+(0.0688P)²+2.4532P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2055
_refine_ls_number_parameters     139
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0475
_refine_ls_wR_factor_ref         0.1421
_refine_ls_wR_factor_gt          0.1415
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_refine_ls_shift/su_max          0.033
_refine_ls_shift/su_mean         0.003
_refine_diff_density_max         0.390
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.050

#------------------------------------------------------------------------------#
#               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'

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
O1 O 0.50110(12) 0.76888(12) 0.64025(6) 0.0338(3) Uani 1 1 d . . . . .
N2 N 0.60686(13) 0.69180(12) 0.64893(7) 0.0235(3) Uani 1 1 d . . . . .
C3 C 0.66926(16) 0.66868(16) 0.72100(9) 0.0275(3) Uani 1 1 d . . . . .
H3 H 0.633315 0.706378 0.762772 0.033 Uiso 1 1 calc R U . . .
C4 C 0.78375(16) 0.59184(16) 0.73562(9) 0.0278(3) Uani 1 1 d . . . . .
H4 H 0.823592 0.574998 0.786871 0.033 Uiso 1 1 calc R U . . .
C5 C 0.83971(15) 0.53994(15) 0.67597(9) 0.0248(3) Uani 1 1 d . . . . .
H5 H 0.919286 0.488292 0.685312 0.030 Uiso 1 1 calc R U . . .
C6 C 0.77721(14) 0.56458(13) 0.60088(8) 0.0204(3) Uani 1 1 d . . . . .
C7 C 0.83797(14) 0.51595(14) 0.53821(9) 0.0227(3) Uani 1 1 d . . . . .
H7 H 0.920438 0.468665 0.547891 0.027 Uiso 1 1 calc R U . . .
C8 C 0.77952(14) 0.53650(14) 0.46575(8) 0.0232(3) Uani 1 1 d . . . . .
H8 H 0.824148 0.507934 0.424849 0.028 Uiso 1 1 calc R U . . .
C9 C 0.65130(14) 0.60061(13) 0.44892(8) 0.0206(3) Uani 1 1 d . . . . .
C10 C 0.58841(16) 0.61066(15) 0.37228(8) 0.0249(3) Uani 1 1 d . . . . .
H10 H 0.634073 0.578971 0.332524 0.030 Uiso 1 1 calc R U . . .
C11 C 0.46278(16) 0.66525(15) 0.35413(9) 0.0268(3) Uani 1 1 d . . . . .
H11 H 0.421827 0.671999 0.302239 0.032 Uiso 1 1 calc R U . . .
C12 C 0.39539(15) 0.71095(15) 0.41275(9) 0.0259(3) Uani 1 1 d . . . . .
H12 H 0.307221 0.746837 0.400370 0.031 Uiso 1 1 calc R U . . .
C13 C 0.45458(15) 0.70487(14) 0.48818(9) 0.0230(3) Uani 1 1 d . . . . .
H13 H 0.4046(19) 0.7364(19) 0.5377(11) 0.028 Uiso 1 1 d . U . . .
C14 C 0.58526(14) 0.65079(13) 0.50867(8) 0.0193(3) Uani 1 1 d . . . . .
C15 C 0.65541(14) 0.63648(13) 0.58635(8) 0.0199(3) 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
O1 N2 1.3115(17) . ?
N2 C3 1.354(2) . ?
N2 C15 1.3930(18) . ?
C3 C4 1.383(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.372(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.404(2) . ?
C5 H5 0.9500 . ?
C6 C15 1.414(2) . ?
C6 C7 1.4297(19) . ?
C7 C8 1.343(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.432(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.410(2) . ?
C9 C14 1.4221(19) . ?
C10 C11 1.369(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.398(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.378(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.416(2) . ?
C13 H13 1.118(19) . ?
C14 C15 1.4537(19) . ?

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
O1 N2 C3 117.85(12) . . ?
O1 N2 C15 121.52(12) . . ?
C3 N2 C15 120.62(13) . . ?
N2 C3 C4 121.96(14) . . ?
N2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C5 C4 C3 119.89(14) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 118.78(14) . . ?
C4 C5 H5 120.6 . . ?
C6 C5 H5 120.6 . . ?
C5 C6 C15 121.11(13) . . ?
C5 C6 C7 119.27(13) . . ?
C15 C6 C7 119.62(13) . . ?
C8 C7 C6 120.60(13) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 121.32(13) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C10 C9 C14 119.80(13) . . ?
C10 C9 C8 119.41(13) . . ?
C14 C9 C8 120.77(13) . . ?
C11 C10 C9 121.20(14) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 119.30(14) . . ?
C10 C11 H11 120.4 . . ?
C12 C11 H11 120.4 . . ?
C13 C12 C11 121.15(14) . . ?
C13 C12 H12 119.4 . . ?
C11 C12 H12 119.4 . . ?
C12 C13 C14 120.87(13) . . ?
C12 C13 H13 124.5(10) . . ?
C14 C13 H13 114.6(10) . . ?
C13 C14 C9 117.63(13) . . ?
C13 C14 C15 125.38(13) . . ?
C9 C14 C15 116.92(13) . . ?
N2 C15 C6 117.41(13) . . ?
N2 C15 C14 122.18(13) . . ?
C6 C15 C14 120.41(12) . . ?

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
O1 N2 C3 C4 -178.07(14) . . . . ?
C15 N2 C3 C4 1.0(2) . . . . ?
N2 C3 C4 C5 2.1(2) . . . . ?
C3 C4 C5 C6 -1.1(2) . . . . ?
C4 C5 C6 C15 -2.8(2) . . . . ?
C4 C5 C6 C7 177.20(13) . . . . ?
C5 C6 C7 C8 179.10(13) . . . . ?
C15 C6 C7 C8 -0.9(2) . . . . ?
C6 C7 C8 C9 -3.7(2) . . . . ?
C7 C8 C9 C10 -174.81(13) . . . . ?
C7 C8 C9 C14 3.4(2) . . . . ?
C14 C9 C10 C11 -1.6(2) . . . . ?
C8 C9 C10 C11 176.62(13) . . . . ?
C9 C10 C11 C12 -0.5(2) . . . . ?
C10 C11 C12 C13 1.6(2) . . . . ?
C11 C12 C13 C14 -0.6(2) . . . . ?
C12 C13 C14 C9 -1.4(2) . . . . ?
C12 C13 C14 C15 -178.28(13) . . . . ?
C10 C9 C14 C13 2.5(2) . . . . ?
C8 C9 C14 C13 -175.71(12) . . . . ?
C10 C9 C14 C15 179.64(12) . . . . ?
C8 C9 C14 C15 1.43(19) . . . . ?
O1 N2 C15 C6 174.24(13) . . . . ?
C3 N2 C15 C6 -4.8(2) . . . . ?
O1 N2 C15 C14 -5.8(2) . . . . ?
C3 N2 C15 C14 175.13(13) . . . . ?
C5 C6 C15 N2 5.8(2) . . . . ?
C7 C6 C15 N2 -174.28(12) . . . . ?
C5 C6 C15 C14 -174.20(12) . . . . ?
C7 C6 C15 C14 5.8(2) . . . . ?
C13 C14 C15 N2 -9.0(2) . . . . ?
C9 C14 C15 N2 174.13(12) . . . . ?
C13 C14 C15 C6 170.98(13) . . . . ?
C9 C14 C15 C6 -5.91(19) . . . . ?

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
#-------------------------------------------------------------------------------
C3 H3 O1 0.95 2.41 3.347(2) 166.8 2_656 yes

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

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



# ............... End of .RES file ........................................... #
#------------------------------------------------------------------------------#

#...............................................................................
# .HKL SHELXL file: job.hkl
#...............................................................................



# ............... End of .HKL file ........................................... #
#------------------------------------------------------------------------------#

#------------------------------------------------------------------------------#
#===END OF CIF FILE FOR VD210                                                  #
#------------------------------------------------------------------------------#
#                                                                              #
################################################################################
####################################################################### 
# 
# 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_VD357t125
_database_code_depnum_ccdc_archive 'CCDC 2480987'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;University of Rennes
France
;
_audit_update_record             
;
2025-08-17 deposited with the CCDC.	2026-04-17 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 13 septembre 2024                                        #
#------------------------------------------------------------------------------#


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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C8 H5 N O3'
_chemical_formula_sum            'C8 H5 N O3'
_chemical_formula_weight         163.13
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND 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                   3.6835(12)
_cell_length_b                   7.721(3)
_cell_length_c                   23.693(9)
_cell_angle_alpha                90
_cell_angle_beta                 93.458(15)
_cell_angle_gamma                90
_cell_volume                     672.6(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1941
_cell_measurement_theta_min      3.1512
_cell_measurement_theta_max      27.4055
_cell_measurement_wavelength     0.710730


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

_diffrn_orient_matrix_UB_11      0.0664872
_diffrn_orient_matrix_UB_21      0.0409835
_diffrn_orient_matrix_UB_31      -0.2605231
_diffrn_orient_matrix_UB_12      -0.1188586
_diffrn_orient_matrix_UB_22      0.0459969
_diffrn_orient_matrix_UB_32      -0.0230976
_diffrn_orient_matrix_UB_13      0.0138466
_diffrn_orient_matrix_UB_23      0.0393242
_diffrn_orient_matrix_UB_33      0.0070575


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

_exptl_crystal_description       stick
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.015
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             336
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.126
_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  0.365
_exptl_absorpt_correction_T_max  0.998

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

# Software                   : BIS V6.2.15/2021-03-15 && APEX4 2022.10-0       #
# Total number of scans:        4                                              #
#                                                                              #
# ....[fast scans included]:                                                   #
#    . Total number of frames :      938                                       #
#    . Total length of scans  :   649.00 (deg.)                                #
#    . Mean rotation speed    :   157.48 sec./deg.                             #
#    . Total exposition time  :     21 h 46 min. [1306 min.]                   #
#                                                                              #
#                                                                              #
# ....[fast scans excluded]:                                                   #
#    . Total number of frames :      578                                       #
#    . Total length of scans  :   289.00 (deg.)                                #
#    . Mean rotation speed    :   240.00 sec./deg.                             #
#    . Total exposition time  :     19 h 16 min. [1156 min.]                   #
#                                                                              #
#                                                                              #
#    Scan  Time(s) Width DX(mm) Frames Range 2Theta  Omega    Phi    Chi  T(K) #
#..............................................................................#
#                                                                              #
#  1 Fast    25.0  1.00    34.0   180  180.0    0.0    0.0    0.0   54.7 150.0 #
#  2 Fast@   25.0  1.00    34.0   180  180.0    0.0    0.0  180.0   54.7 150.0 #
#  3 Phi    120.0  0.50    34.0   384  192.0    0.1  270.3  156.0   24.0 150.0 #
#  4 Omega  120.0  0.50    34.0   194   97.0    0.1    2.7  144.0  -44.5 150.0 #
#                                                                              #
#  @: attenuated beam                                                          #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 CMOS-PHOTON70
_diffrn_detector_area_resol_mean 7.39
_diffrn_ambient_temperature      150(2)
_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           1.00
_diffrn_source_voltage           50.00
_diffrn_source_power             50.0
_diffrn_reflns_av_uneti/neti     0.0976
_diffrn_reflns_av_r_equivalents  0.1189
_diffrn_reflns_number            6052
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.775
_diffrn_reflns_theta_max         26.368
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.993
_reflns_number_total             1372
_reflns_number_gt                1012
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.
;

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

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019_2 (Sheldrick, 2019)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2024)'

#------------------------------------------------------------------------------#
#                            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)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         1372
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1598
_refine_ls_R_factor_gt           0.1331
_refine_ls_wR_factor_ref         0.3726
_refine_ls_wR_factor_gt          0.3543
_refine_ls_goodness_of_fit_ref   1.411
_refine_ls_restrained_S_all      1.411
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.693
_refine_diff_density_min         -0.724
_refine_diff_density_rms         0.182

#------------------------------------------------------------------------------#
#               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'

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
N1 N 0.5582(14) 0.9291(6) 0.57490(19) 0.0302(12) Uani 1 1 d . . . . .
H1 H 0.611468 1.026953 0.558236 0.036 Uiso 1 1 calc R U . . .
C2 C 0.3891(16) 0.7903(6) 0.5471(2) 0.0272(13) Uani 1 1 d . . . . .
O3 O 0.2885(12) 0.7881(5) 0.49744(15) 0.0352(12) Uani 1 1 d . . . . .
C4 C 0.3538(14) 0.6555(6) 0.5907(2) 0.0230(12) Uani 1 1 d . . . . .
C5 C 0.2067(16) 0.4899(6) 0.5848(2) 0.0286(13) Uani 1 1 d . . . . .
H5 H 0.106398 0.446840 0.549652 0.034 Uiso 1 1 calc R U . . .
C6 C 0.2177(16) 0.3921(7) 0.6342(3) 0.0329(14) Uani 1 1 d . . . . .
H6 H 0.121745 0.277919 0.632679 0.040 Uiso 1 1 calc R U . . .
C7 C 0.3618(16) 0.4539(7) 0.6853(2) 0.0293(14) Uani 1 1 d . . . . .
H7 H 0.361270 0.382287 0.717860 0.035 Uiso 1 1 calc R U . . .
C8 C 0.5082(15) 0.6197(7) 0.6898(2) 0.0259(13) Uani 1 1 d . . . . .
O9 O 0.6570(13) 0.6808(6) 0.73864(17) 0.0431(13) Uani 1 1 d . . . . .
H9 H 0.690804 0.598883 0.761674 0.065 Uiso 1 1 calc R U . . .
C10 C 0.5009(14) 0.7208(6) 0.6423(2) 0.0242(13) Uani 1 1 d . . . . .
C11 C 0.6336(16) 0.8965(6) 0.6318(2) 0.0265(13) Uani 1 1 d . . . . .
O12 O 0.7903(12) 0.9994(5) 0.66374(15) 0.0333(11) 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
N1 C11 1.382(7) . ?
N1 C2 1.386(7) . ?
N1 H1 0.8800 . ?
C2 O3 1.211(6) . ?
C2 C4 1.479(7) . ?
C4 C5 1.393(7) . ?
C4 C10 1.401(7) . ?
C5 C6 1.392(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.376(8) . ?
C6 H6 0.9500 . ?
C7 C8 1.391(7) . ?
C7 H7 0.9500 . ?
C8 O9 1.336(6) . ?
C8 C10 1.369(7) . ?
O9 H9 0.8400 . ?
C10 C11 1.469(7) . ?
C11 O12 1.219(6) . ?

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
C11 N1 C2 112.4(4) . . ?
C11 N1 H1 123.8 . . ?
C2 N1 H1 123.8 . . ?
O3 C2 N1 125.1(5) . . ?
O3 C2 C4 129.4(5) . . ?
N1 C2 C4 105.5(4) . . ?
C5 C4 C10 123.1(5) . . ?
C5 C4 C2 128.7(5) . . ?
C10 C4 C2 108.2(4) . . ?
C6 C5 C4 114.9(5) . . ?
C6 C5 H5 122.5 . . ?
C4 C5 H5 122.5 . . ?
C7 C6 C5 122.8(5) . . ?
C7 C6 H6 118.6 . . ?
C5 C6 H6 118.6 . . ?
C6 C7 C8 121.0(5) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
O9 C8 C10 119.8(5) . . ?
O9 C8 C7 122.0(5) . . ?
C10 C8 C7 118.2(5) . . ?
C8 O9 H9 109.5 . . ?
C8 C10 C4 120.0(5) . . ?
C8 C10 C11 132.5(5) . . ?
C4 C10 C11 107.4(4) . . ?
O12 C11 N1 123.2(5) . . ?
O12 C11 C10 130.3(5) . . ?
N1 C11 C10 106.5(4) . . ?

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
C11 N1 C2 O3 178.3(6) . . . . ?
C11 N1 C2 C4 -0.1(6) . . . . ?
O3 C2 C4 C5 2.6(10) . . . . ?
N1 C2 C4 C5 -179.1(5) . . . . ?
O3 C2 C4 C10 -177.9(6) . . . . ?
N1 C2 C4 C10 0.4(6) . . . . ?
C10 C4 C5 C6 -0.3(8) . . . . ?
C2 C4 C5 C6 179.1(5) . . . . ?
C4 C5 C6 C7 0.2(9) . . . . ?
C5 C6 C7 C8 -0.5(9) . . . . ?
C6 C7 C8 O9 -178.4(5) . . . . ?
C6 C7 C8 C10 0.9(8) . . . . ?
O9 C8 C10 C4 178.3(5) . . . . ?
C7 C8 C10 C4 -1.0(8) . . . . ?
O9 C8 C10 C11 0.5(9) . . . . ?
C7 C8 C10 C11 -178.8(6) . . . . ?
C5 C4 C10 C8 0.8(8) . . . . ?
C2 C4 C10 C8 -178.8(5) . . . . ?
C5 C4 C10 C11 179.0(5) . . . . ?
C2 C4 C10 C11 -0.5(6) . . . . ?
C2 N1 C11 O12 178.0(6) . . . . ?
C2 N1 C11 C10 -0.2(6) . . . . ?
C8 C10 C11 O12 0.4(11) . . . . ?
C4 C10 C11 O12 -177.6(6) . . . . ?
C8 C10 C11 N1 178.5(6) . . . . ?
C4 C10 C11 N1 0.5(6) . . . . ?

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

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



# ............... End of .RES file ........................................... #
#------------------------------------------------------------------------------#

#...............................................................................
# .HKL SHELXL file: job.hkl
#...............................................................................



# ............... End of .HKL file ........................................... #
#------------------------------------------------------------------------------#

#------------------------------------------------------------------------------#
#===END OF CIF FILE FOR VD357T125                                              #
#------------------------------------------------------------------------------#
#                                                                              #
################################################################################
####################################################################### 
# 
# 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_VD103t2
_database_code_depnum_ccdc_archive 'CCDC 2480986'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;University of Rennes
France
;
_audit_update_record             
;
2025-08-17 deposited with the CCDC.	2026-04-17 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 06 fevrier 2024                                          #
#------------------------------------------------------------------------------#


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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C9 H7 N O3, H2 O'
_chemical_formula_sum            'C9 H9 N O4'
_chemical_formula_weight         195.17
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   7.7600(9)
_cell_length_b                   15.7208(15)
_cell_length_c                   7.2123(8)
_cell_angle_alpha                90
_cell_angle_beta                 92.363(4)
_cell_angle_gamma                90
_cell_volume                     879.10(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    8112
_cell_measurement_theta_min      2.6270
_cell_measurement_theta_max      27.4883
_cell_measurement_wavelength     0.710730


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

_diffrn_orient_matrix_UB_11      0.0895955
_diffrn_orient_matrix_UB_21      0.0984619
_diffrn_orient_matrix_UB_31      -0.0391778
_diffrn_orient_matrix_UB_12      -0.0330165
_diffrn_orient_matrix_UB_22      0.0086875
_diffrn_orient_matrix_UB_32      -0.0536719
_diffrn_orient_matrix_UB_13      -0.0687472
_diffrn_orient_matrix_UB_23      0.0928592
_diffrn_orient_matrix_UB_33      0.0573206


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

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.580
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.350
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.475
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             408
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.118
_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  0.917
_exptl_absorpt_correction_T_max  0.960

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

# Software                   : BIS V6.2.15/2021-03-15 && APEX4 2022.10-0       #
# Total number of scans:        4                                              #
#                                                                              #
# ....[fast scans included]:                                                   #
#    . Total number of frames :      688                                       #
#    . Total length of scans  :   688.00 (deg.)                                #
#    . Mean rotation speed    :     2.43 sec./deg.                             #
#    . Total exposition time  :           27 min.                              #
#                                                                              #
#                                                                              #
# ....[fast scans excluded]:                                                   #
#    . Total number of frames :      328                                       #
#    . Total length of scans  :   328.00 (deg.)                                #
#    . Mean rotation speed    :     4.00 sec./deg.                             #
#    . Total exposition time  :           21 min.                              #
#                                                                              #
#                                                                              #
#    Scan  Time(s) Width DX(mm) Frames Range 2Theta  Omega    Phi    Chi  T(K) #
#..............................................................................#
#                                                                              #
#  1 Fast     1.0  1.00    34.0   180  180.0    0.0    0.0    0.0   54.7 150.0 #
#  2 Fast@    1.0  1.00    34.0   180  180.0    0.0    0.0  180.0   54.7 150.0 #
#  3 Phi      4.0  1.00    34.0   185  185.0    0.1    2.4  260.0  -44.5 150.0 #
#  4 Phi      4.0  1.00    34.0   143  143.0    0.1  270.3  151.5   24.0 150.0 #
#                                                                              #
#  @: attenuated beam                                                          #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 CMOS-PHOTON70
_diffrn_detector_area_resol_mean 7.39
_diffrn_ambient_temperature      150(2)
_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           1.00
_diffrn_source_voltage           50.00
_diffrn_source_power             50.0
_diffrn_reflns_av_uneti/neti     0.0207
_diffrn_reflns_av_r_equivalents  0.0317
_diffrn_reflns_number            10428
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.591
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             2011
_reflns_number_gt                1851
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.
;

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

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019_2 (Sheldrick, 2019)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2023)'

#------------------------------------------------------------------------------#
#                            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)+(0.0483P)²+0.5175P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2011
_refine_ls_number_parameters     137
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1085
_refine_ls_wR_factor_gt          0.1059
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.001
_refine_diff_density_max         0.503
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.045

#------------------------------------------------------------------------------#
#               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'

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
O1 O 0.12764(14) 0.58053(6) 0.45797(15) 0.0283(3) Uani 1 1 d . . . . .
H1 H 0.030(3) 0.5916(12) 0.526(3) 0.034 Uiso 1 1 d . U . . .
C2 C 0.21146(18) 0.65262(8) 0.42148(18) 0.0211(3) Uani 1 1 d . . . . .
C3 C 0.14275(18) 0.73443(9) 0.45023(18) 0.0224(3) Uani 1 1 d . . . . .
H3 H 0.030756 0.740040 0.497268 0.027 Uiso 1 1 calc R U . . .
C4 C 0.23650(18) 0.80660(9) 0.41075(19) 0.0237(3) Uani 1 1 d . . . . .
H4 H 0.186460 0.860835 0.430506 0.028 Uiso 1 1 calc R U . . .
C5 C 0.40306(18) 0.80234(9) 0.34249(18) 0.0229(3) Uani 1 1 d . . . . .
H5 H 0.467524 0.852105 0.317384 0.027 Uiso 1 1 calc R U . . .
C6 C 0.46783(17) 0.72223(9) 0.31396(18) 0.0210(3) Uani 1 1 d . . . . .
C7 C 0.63453(17) 0.69540(9) 0.23806(18) 0.0227(3) Uani 1 1 d . . . . .
O8 O 0.75457(13) 0.73857(7) 0.18971(15) 0.0305(3) Uani 1 1 d . . . . .
N9 N 0.63061(15) 0.60745(8) 0.22871(16) 0.0239(3) Uani 1 1 d . . . . .
C10 C 0.76686(19) 0.55533(10) 0.1558(2) 0.0304(3) Uani 1 1 d . . . . .
H10A H 0.727191 0.530651 0.036758 0.046 Uiso 1 1 calc R U . . .
H10B H 0.796371 0.509592 0.243780 0.046 Uiso 1 1 calc R U . . .
H10C H 0.868909 0.590612 0.137608 0.046 Uiso 1 1 calc R U . . .
C11 C 0.47604(17) 0.57462(9) 0.29096(18) 0.0219(3) Uani 1 1 d . . . . .
O12 O 0.44001(14) 0.49932(6) 0.28681(15) 0.0285(3) Uani 1 1 d . . . . .
C13 C 0.37461(17) 0.64843(8) 0.34960(17) 0.0203(3) Uani 1 1 d . . . . .
OW1 O 0.86902(16) 0.59668(8) 0.6685(2) 0.0426(3) Uani 1 1 d . . . . .
H1A H 0.787(3) 0.5570(15) 0.661(3) 0.051 Uiso 1 1 d . U . . .
H1B H 0.811(3) 0.6467(15) 0.677(3) 0.051 Uiso 1 1 d . U . . .



#------------------------------------------------------------------------------#
#                              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
O1 C2 1.3382(16) . ?
O1 H1 0.93(2) . ?
C2 C13 1.3893(19) . ?
C2 C3 1.4109(19) . ?
C3 C4 1.3837(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.404(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.3746(19) . ?
C5 H5 0.9500 . ?
C6 C13 1.3967(18) . ?
C6 C7 1.4864(19) . ?
C7 O8 1.2152(17) . ?
C7 N9 1.3845(19) . ?
N9 C11 1.3968(17) . ?
N9 C10 1.4531(18) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 O12 1.2164(17) . ?
C11 C13 1.4739(18) . ?
OW1 H1A 0.89(3) . ?
OW1 H1B 0.91(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
C2 O1 H1 110.8(11) . . ?
O1 C2 C13 119.41(12) . . ?
O1 C2 C3 123.60(12) . . ?
C13 C2 C3 116.99(12) . . ?
C4 C3 C2 120.81(13) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 122.18(13) . . ?
C3 C4 H4 118.9 . . ?
C5 C4 H4 118.9 . . ?
C6 C5 C4 116.35(12) . . ?
C6 C5 H5 121.8 . . ?
C4 C5 H5 121.8 . . ?
C5 C6 C13 122.56(13) . . ?
C5 C6 C7 130.11(12) . . ?
C13 C6 C7 107.29(12) . . ?
O8 C7 N9 124.01(13) . . ?
O8 C7 C6 129.51(13) . . ?
N9 C7 C6 106.48(11) . . ?
C7 N9 C11 111.76(11) . . ?
C7 N9 C10 124.46(12) . . ?
C11 N9 C10 123.73(12) . . ?
N9 C10 H10A 109.5 . . ?
N9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O12 C11 N9 123.45(13) . . ?
O12 C11 C13 130.41(13) . . ?
N9 C11 C13 106.09(11) . . ?
C2 C13 C6 121.07(12) . . ?
C2 C13 C11 130.55(12) . . ?
C6 C13 C11 108.32(12) . . ?
H1A OW1 H1B 105(2) . . ?

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
O1 C2 C3 C4 179.59(13) . . . . ?
C13 C2 C3 C4 -1.03(19) . . . . ?
C2 C3 C4 C5 -0.5(2) . . . . ?
C3 C4 C5 C6 1.0(2) . . . . ?
C4 C5 C6 C13 0.20(19) . . . . ?
C4 C5 C6 C7 177.65(13) . . . . ?
C5 C6 C7 O8 2.9(2) . . . . ?
C13 C6 C7 O8 -179.39(14) . . . . ?
C5 C6 C7 N9 -176.52(13) . . . . ?
C13 C6 C7 N9 1.23(14) . . . . ?
O8 C7 N9 C11 -179.17(13) . . . . ?
C6 C7 N9 C11 0.25(15) . . . . ?
O8 C7 N9 C10 -1.7(2) . . . . ?
C6 C7 N9 C10 177.76(12) . . . . ?
C7 N9 C11 O12 176.21(13) . . . . ?
C10 N9 C11 O12 -1.3(2) . . . . ?
C7 N9 C11 C13 -1.55(14) . . . . ?
C10 N9 C11 C13 -179.09(12) . . . . ?
O1 C2 C13 C6 -178.43(12) . . . . ?
C3 C2 C13 C6 2.17(19) . . . . ?
O1 C2 C13 C11 4.6(2) . . . . ?
C3 C2 C13 C11 -174.85(13) . . . . ?
C5 C6 C13 C2 -1.8(2) . . . . ?
C7 C6 C13 C2 -179.78(12) . . . . ?
C5 C6 C13 C11 175.79(12) . . . . ?
C7 C6 C13 C11 -2.16(14) . . . . ?
O12 C11 C13 C2 2.1(2) . . . . ?
N9 C11 C13 C2 179.62(13) . . . . ?
O12 C11 C13 C6 -175.24(14) . . . . ?
N9 C11 C13 C6 2.31(14) . . . . ?

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

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



# ............... End of .RES file ........................................... #
#------------------------------------------------------------------------------#

#...............................................................................
# .HKL SHELXL file: job.hkl
#...............................................................................



# ............... End of .HKL file ........................................... #
#------------------------------------------------------------------------------#

#------------------------------------------------------------------------------#
#===END OF CIF FILE FOR VD103T2                                                #
#------------------------------------------------------------------------------#
#                                                                              #
################################################################################
####################################################################### 
# 
# 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_VD250
_database_code_depnum_ccdc_archive 'CCDC 2480984'
loop_
_audit_author_name
_audit_author_address
'Thierry Roisnel'
;University of Rennes
France
;
_audit_update_record             
;
2025-08-17 deposited with the CCDC.	2026-04-17 downloaded from the CCDC.
;

#------------------------------------------------------------------------------#
# Date of experiment: 04 avril 2024                                            #
#------------------------------------------------------------------------------#


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

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H22 N4'
_chemical_formula_sum            'C22 H22 N4'
_chemical_formula_weight         342.43
_chemical_compound_source        'synthesis as described'

#------------------------------------------------------------------------------#
#                    SPACE GROUP AND UNIT CELL INFORMATION                     #
#------------------------------------------------------------------------------#

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'
_space_group_IT_number           15
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   13.7447(7)
_cell_length_b                   10.2530(5)
_cell_length_c                   26.4835(15)
_cell_angle_alpha                90
_cell_angle_beta                 101.540(2)
_cell_angle_gamma                90
_cell_volume                     3656.7(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4654
_cell_measurement_theta_min      2.5248
_cell_measurement_theta_max      27.2594
_cell_measurement_wavelength     0.710730


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

_diffrn_orient_matrix_UB_11      0.0095405
_diffrn_orient_matrix_UB_21      0.0548919
_diffrn_orient_matrix_UB_31      0.0490908
_diffrn_orient_matrix_UB_12      -0.0013123
_diffrn_orient_matrix_UB_22      -0.0648847
_diffrn_orient_matrix_UB_32      0.0728072
_diffrn_orient_matrix_UB_13      0.0384335
_diffrn_orient_matrix_UB_23      0.0017420
_diffrn_orient_matrix_UB_33      0.0022451


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

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.090
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1456
_exptl_special_details           
;
 ?
;

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

_exptl_absorpt_coefficient_mu    0.076
_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  0.828
_exptl_absorpt_correction_T_max  0.993

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

# Software                   : BIS V6.2.15/2021-03-15 && APEX4 2022.10-0       #
# Total number of scans:        2                                              #
#                                                                              #
# ....[fast scans included]:                                                   #
#    . Total number of frames :      364                                       #
#    . Total length of scans  :   364.00 (deg.)                                #
#    . Mean rotation speed    :     5.55 sec./deg.                             #
#    . Total exposition time  :           33 min.                              #
#                                                                              #
#                                                                              #
# ....[fast scans excluded]:                                                   #
#    . Total number of frames :      184                                       #
#    . Total length of scans  :   184.00 (deg.)                                #
#    . Mean rotation speed    :    10.00 sec./deg.                             #
#    . Total exposition time  :           30 min.                              #
#                                                                              #
#                                                                              #
#    Scan  Time(s) Width DX(mm) Frames Range 2Theta  Omega    Phi    Chi  T(K) #
#..............................................................................#
#                                                                              #
#  1 Fast     1.0  1.00    34.0   180  180.0    0.0    0.0    0.0   54.7 150.0 #
#  2 Phi     10.0  1.00    34.0   184  184.0    0.1    1.9  180.0  -24.0 150.0 #
#                                                                              #
#..............................................................................#

_diffrn_measurement_device_type  'D8 VENTURE Bruker AXS'
_diffrn_measurement_method       'rotation images'
_diffrn_detector                 CMOS-PHOTON70
_diffrn_detector_area_resol_mean 7.39
_diffrn_ambient_temperature      150(2)
_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           1.00
_diffrn_source_voltage           50.00
_diffrn_source_power             50.0
_diffrn_reflns_av_uneti/neti     0.0446
_diffrn_reflns_av_r_equivalents  0.0432
_diffrn_reflns_number            12832
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_theta_min         2.497
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.989
_reflns_number_total             4140
_reflns_number_gt                3279
_reflns_threshold_expression     >2sigma(I)

_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal class for the
calculation of statistics and refinement.
;

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

_computing_data_collection       'Bruker APEX3 (Bruker, 2015)'
_computing_cell_refinement       'APEX3 (Bruker, 2015)'
_computing_data_reduction        'SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2018_2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2019_2 (Sheldrick, 2019)'
_computing_molecular_graphics    
;
   'SXGRAPH (L. Farrugia, 1999), Mercury (CSD, 2020)'
;
_computing_publication_material  'CRYSCALC (T. Roisnel, local program, 2024)'

#------------------------------------------------------------------------------#
#                            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)+(0.0473P)²+3.2528P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4140
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0545
_refine_ls_wR_factor_ref         0.1266
_refine_ls_wR_factor_gt          0.1174
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.046

#------------------------------------------------------------------------------#
#               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'

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 0.23703(12) 0.86068(16) 0.27444(6) 0.0274(4) Uani 1 1 d . . . . .
C2 C 0.14034(16) 0.7893(2) 0.25164(9) 0.0551(6) Uani 1 1 d . . . . .
H2A H 0.096314 0.847971 0.228288 0.083 Uiso 1 1 calc R U . . .
H2B H 0.107602 0.761818 0.279521 0.083 Uiso 1 1 calc R U . . .
H2C H 0.155236 0.712515 0.232500 0.083 Uiso 1 1 calc R U . . .
C3 C 0.21267(16) 0.9810(2) 0.30330(7) 0.0434(5) Uani 1 1 d . . . . .
H3A H 0.274029 1.028340 0.317376 0.065 Uiso 1 1 calc R U . . .
H3B H 0.180574 0.954170 0.331519 0.065 Uiso 1 1 calc R U . . .
H3C H 0.167724 1.037786 0.279580 0.065 Uiso 1 1 calc R U . . .
C4 C 0.28427(16) 0.9056(2) 0.23002(8) 0.0464(5) Uani 1 1 d . . . . .
H4A H 0.346394 0.951657 0.243749 0.070 Uiso 1 1 calc R U . . .
H4B H 0.238603 0.964333 0.207596 0.070 Uiso 1 1 calc R U . . .
H4C H 0.298173 0.829602 0.210152 0.070 Uiso 1 1 calc R U . . .
C5 C 0.30473(12) 0.76816(16) 0.31104(6) 0.0234(3) Uani 1 1 d . . . . .
C6 C 0.39586(12) 0.72488(17) 0.30237(6) 0.0273(4) Uani 1 1 d . . . . .
H6 H 0.419485 0.757491 0.273476 0.033 Uiso 1 1 calc R U . . .
C7 C 0.45319(12) 0.63567(17) 0.33460(6) 0.0273(4) Uani 1 1 d . . . . .
H7 H 0.514963 0.607994 0.327399 0.033 Uiso 1 1 calc R U . . .
C8 C 0.42120(11) 0.58606(15) 0.37750(6) 0.0227(3) Uani 1 1 d . . . . .
C9 C 0.33135(12) 0.63131(16) 0.38736(6) 0.0240(3) Uani 1 1 d . . . . .
H9 H 0.308511 0.600248 0.416727 0.029 Uiso 1 1 calc R U . . .
C10 C 0.27490(12) 0.72074(16) 0.35507(6) 0.0251(3) Uani 1 1 d . . . . .
H10 H 0.214288 0.750774 0.362974 0.030 Uiso 1 1 calc R U . . .
C11 C 0.48029(12) 0.48805(16) 0.41070(6) 0.0242(3) Uani 1 1 d . . . . .
N12 N 0.57651(11) 0.46168(16) 0.40789(6) 0.0359(4) Uani 1 1 d . . . . .
N13 N 0.61080(10) 0.36841(15) 0.44045(6) 0.0354(4) Uani 1 1 d . . . . .
N14 N 0.53669(9) 0.33509(13) 0.46449(5) 0.0226(3) Uani 1 1 d . . . . .
C15 C 0.45486(11) 0.40736(16) 0.44713(6) 0.0233(3) Uani 1 1 d . . . . .
H15 H 0.392992 0.403162 0.457858 0.028 Uiso 1 1 calc R U . . .
C16 C 0.54900(11) 0.23071(15) 0.50091(6) 0.0215(3) Uani 1 1 d . . . . .
C17 C 0.63404(11) 0.15230(16) 0.50636(6) 0.0249(3) Uani 1 1 d . . . . .
H17 H 0.683891 0.168035 0.486903 0.030 Uiso 1 1 calc R U . . .
C18 C 0.64179(12) 0.05233(16) 0.54095(6) 0.0266(4) Uani 1 1 d . . . . .
H18 H 0.698084 -0.003484 0.546004 0.032 Uiso 1 1 calc R U . . .
C19 C 0.56628(12) 0.03168(16) 0.56924(6) 0.0248(3) Uani 1 1 d . . . . .
C20 C 0.56843(13) -0.07293(17) 0.60436(7) 0.0305(4) Uani 1 1 d . . . . .
H20 H 0.621518 -0.133926 0.609214 0.037 Uiso 1 1 calc R U . . .
C21 C 0.49407(14) -0.08576(18) 0.63117(7) 0.0344(4) Uani 1 1 d . . . . .
H21 H 0.495541 -0.155948 0.654731 0.041 Uiso 1 1 calc R U . . .
C22 C 0.41522(13) 0.00397(18) 0.62426(6) 0.0310(4) Uani 1 1 d . . . . .
H22 H 0.365266 -0.005709 0.644130 0.037 Uiso 1 1 calc R U . . .
C23 C 0.40798(12) 0.10530(17) 0.58971(6) 0.0265(4) Uani 1 1 d . . . . .
C24 C 0.32289(13) 0.19938(19) 0.58163(7) 0.0346(4) Uani 1 1 d . . . . .
H24A H 0.277448 0.176488 0.604423 0.052 Uiso 1 1 calc R U . . .
H24B H 0.287403 0.195215 0.545679 0.052 Uiso 1 1 calc R U . . .
H24C H 0.348149 0.287988 0.589500 0.052 Uiso 1 1 calc R U . . .
C25 C 0.48502(11) 0.11921(15) 0.56124(6) 0.0226(3) Uani 1 1 d . . . . .
N26 N 0.47705(9) 0.21886(13) 0.52612(5) 0.0222(3) 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 C3 1.523(3) . ?
C1 C4 1.524(2) . ?
C1 C5 1.531(2) . ?
C1 C2 1.531(3) . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C3 H3C 0.9800 . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.390(2) . ?
C5 C10 1.398(2) . ?
C6 C7 1.384(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.394(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.392(2) . ?
C8 C11 1.469(2) . ?
C9 C10 1.382(2) . ?
C9 H9 0.9500 . ?
C10 H10 0.9500 . ?
C11 N12 1.366(2) . ?
C11 C15 1.368(2) . ?
N12 N13 1.311(2) . ?
N13 N14 1.3487(18) . ?
N14 C15 1.349(2) . ?
N14 C16 1.428(2) . ?
C15 H15 0.9500 . ?
C16 N26 1.305(2) . ?
C16 C17 1.402(2) . ?
C17 C18 1.365(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.412(2) . ?
C18 H18 0.9500 . ?
C19 C25 1.415(2) . ?
C19 C20 1.416(2) . ?
C20 C21 1.362(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.405(3) . ?
C21 H21 0.9500 . ?
C22 C23 1.375(2) . ?
C22 H22 0.9500 . ?
C23 C25 1.425(2) . ?
C23 C24 1.498(2) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 N26 1.371(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
C3 C1 C4 108.25(16) . . ?
C3 C1 C5 110.54(14) . . ?
C4 C1 C5 112.14(14) . . ?
C3 C1 C2 108.92(17) . . ?
C4 C1 C2 108.05(16) . . ?
C5 C1 C2 108.86(14) . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C1 C3 H3A 109.5 . . ?
C1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C1 C4 H4A 109.5 . . ?
C1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C6 C5 C10 116.78(15) . . ?
C6 C5 C1 123.15(14) . . ?
C10 C5 C1 120.05(14) . . ?
C7 C6 C5 121.98(15) . . ?
C7 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
C6 C7 C8 120.67(15) . . ?
C6 C7 H7 119.7 . . ?
C8 C7 H7 119.7 . . ?
C9 C8 C7 117.88(15) . . ?
C9 C8 C11 121.40(14) . . ?
C7 C8 C11 120.72(14) . . ?
C10 C9 C8 120.97(14) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C9 C10 C5 121.66(15) . . ?
C9 C10 H10 119.2 . . ?
C5 C10 H10 119.2 . . ?
N12 C11 C15 107.78(14) . . ?
N12 C11 C8 121.88(14) . . ?
C15 C11 C8 130.33(14) . . ?
N13 N12 C11 109.45(14) . . ?
N12 N13 N14 106.82(13) . . ?
C15 N14 N13 110.92(13) . . ?
C15 N14 C16 128.33(13) . . ?
N13 N14 C16 120.67(13) . . ?
N14 C15 C11 105.04(14) . . ?
N14 C15 H15 127.5 . . ?
C11 C15 H15 127.5 . . ?
N26 C16 C17 126.54(15) . . ?
N26 C16 N14 114.58(14) . . ?
C17 C16 N14 118.88(14) . . ?
C18 C17 C16 116.84(15) . . ?
C18 C17 H17 121.6 . . ?
C16 C17 H17 121.6 . . ?
C17 C18 C19 120.11(15) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C18 C19 C25 117.87(15) . . ?
C18 C19 C20 122.75(16) . . ?
C25 C19 C20 119.38(15) . . ?
C21 C20 C19 119.75(17) . . ?
C21 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C20 C21 C22 120.55(16) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C23 C22 C21 122.18(16) . . ?
C23 C22 H22 118.9 . . ?
C21 C22 H22 118.9 . . ?
C22 C23 C25 117.74(16) . . ?
C22 C23 C24 122.15(15) . . ?
C25 C23 C24 120.11(15) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
N26 C25 C19 121.83(14) . . ?
N26 C25 C23 117.82(15) . . ?
C19 C25 C23 120.35(15) . . ?
C16 N26 C25 116.79(14) . . ?

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
C3 C1 C5 C6 -124.59(18) . . . . ?
C4 C1 C5 C6 -3.7(2) . . . . ?
C2 C1 C5 C6 115.81(19) . . . . ?
C3 C1 C5 C10 56.9(2) . . . . ?
C4 C1 C5 C10 177.75(16) . . . . ?
C2 C1 C5 C10 -62.7(2) . . . . ?
C10 C5 C6 C7 2.2(2) . . . . ?
C1 C5 C6 C7 -176.42(16) . . . . ?
C5 C6 C7 C8 -0.3(3) . . . . ?
C6 C7 C8 C9 -1.4(2) . . . . ?
C6 C7 C8 C11 177.87(15) . . . . ?
C7 C8 C9 C10 1.2(2) . . . . ?
C11 C8 C9 C10 -178.12(15) . . . . ?
C8 C9 C10 C5 0.8(2) . . . . ?
C6 C5 C10 C9 -2.4(2) . . . . ?
C1 C5 C10 C9 176.21(15) . . . . ?
C9 C8 C11 N12 -166.82(16) . . . . ?
C7 C8 C11 N12 13.9(2) . . . . ?
C9 C8 C11 C15 14.8(3) . . . . ?
C7 C8 C11 C15 -164.48(17) . . . . ?
C15 C11 N12 N13 0.5(2) . . . . ?
C8 C11 N12 N13 -178.25(15) . . . . ?
C11 N12 N13 N14 -0.3(2) . . . . ?
N12 N13 N14 C15 0.06(19) . . . . ?
N12 N13 N14 C16 176.94(14) . . . . ?
N13 N14 C15 C11 0.23(18) . . . . ?
C16 N14 C15 C11 -176.36(14) . . . . ?
N12 C11 C15 N14 -0.41(18) . . . . ?
C8 C11 C15 N14 178.16(15) . . . . ?
C15 N14 C16 N26 -11.9(2) . . . . ?
N13 N14 C16 N26 171.80(14) . . . . ?
C15 N14 C16 C17 168.00(15) . . . . ?
N13 N14 C16 C17 -8.3(2) . . . . ?
N26 C16 C17 C18 1.0(2) . . . . ?
N14 C16 C17 C18 -178.86(14) . . . . ?
C16 C17 C18 C19 0.0(2) . . . . ?
C17 C18 C19 C25 -1.4(2) . . . . ?
C17 C18 C19 C20 177.80(15) . . . . ?
C18 C19 C20 C21 178.73(16) . . . . ?
C25 C19 C20 C21 -2.0(2) . . . . ?
C19 C20 C21 C22 0.0(3) . . . . ?
C20 C21 C22 C23 1.8(3) . . . . ?
C21 C22 C23 C25 -1.3(2) . . . . ?
C21 C22 C23 C24 178.79(16) . . . . ?
C18 C19 C25 N26 2.1(2) . . . . ?
C20 C19 C25 N26 -177.21(14) . . . . ?
C18 C19 C25 C23 -178.31(14) . . . . ?
C20 C19 C25 C23 2.4(2) . . . . ?
C22 C23 C25 N26 178.90(14) . . . . ?
C24 C23 C25 N26 -1.2(2) . . . . ?
C22 C23 C25 C19 -0.7(2) . . . . ?
C24 C23 C25 C19 179.13(15) . . . . ?
C17 C16 N26 C25 -0.5(2) . . . . ?
N14 C16 N26 C25 179.43(12) . . . . ?
C19 C25 N26 C16 -1.1(2) . . . . ?
C23 C25 N26 C16 179.24(14) . . . . ?

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

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



# ............... End of .RES file ........................................... #
#------------------------------------------------------------------------------#

#...............................................................................
# .HKL SHELXL file: job.hkl
#...............................................................................



# ............... End of .HKL file ........................................... #
#------------------------------------------------------------------------------#

#------------------------------------------------------------------------------#
#===END OF CIF FILE FOR VD250                                                  #
#------------------------------------------------------------------------------#
#                                                                              #
################################################################################
