 
data_TA2
#v586_GuillotICMMO

_publ_contact_author_name        'Gilles CLAVIER'
_publ_contact_author_address     
;Laboratoire de Photophysique et Photochimie 
Supramoléculaires et Macromoléculaires (PPSM),
École normale supérieure de Cachan,
Uniersiré Paris-Saclay,
61 avenue du Président Wilson,
94235 Cachan cedex,
France.
;
_publ_contact_author_email       Gilles.CLAVIER@ppsm.ens-cachan.fr
loop_
_publ_author_name
_publ_author_address
'Qu, Yangyang'
;Laboratoire de Photophysique et Photochimie 
Supramoléculaires et Macromoléculaires (PPSM),
École normale supérieure de Cachan,
Uniersiré Paris-Saclay,
61 avenue du Président Wilson,
94235 Cachan cedex,
France.
;
"Guillot, Régis"
;Institut de Chimie Moléculaire et des Matériaux d'Orsay (ICMMO),
Bâtiments 420, 
Université Paris-Sud 11, 
Université Paris-Saclay, 
UMR CNRS 8182, 
Rue du doyen Georges Poitou,
91405 Orsay cedex,
France.
;
'Clavier, Gilles'
;Laboratoire de Photophysique et Photochimie 
Supramoléculaires et Macromoléculaires (PPSM),
École normale supérieure de Cachan,
Uniersiré Paris-Saclay,
61 avenue du Président Wilson,
94235 Cachan cedex,
France.
;

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         'C20 H13 N5 O'
_chemical_formula_sum            'C20 H13 N5 O'
_chemical_melting_point          ?

_exptl_crystal_description       plate
_exptl_crystal_colour            'dark red'
_diffrn_ambient_temperature      100(1)
_chemical_formula_weight         339.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0034 0.0017 '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 0.0066 0.0034 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0114 0.0062 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_chemical_absolute_configuration .

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

_cell_length_a                   7.8191(7)
_cell_length_b                   8.2110(8)
_cell_length_c                   13.3817(13)
_cell_angle_alpha                80.524(3)
_cell_angle_beta                 73.188(3)
_cell_angle_gamma                67.372(3)
_cell_volume                     757.73(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(1)
_cell_measurement_reflns_used    9698
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      31.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.487
_exptl_crystal_F_000             352
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.130
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.035
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.988
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8915
_exptl_absorpt_correction_T_max  0.9462
_exptl_absorpt_process_details   'apex3 Bruker'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker VENTURE PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            49942
_diffrn_reflns_av_unetI/netI     0.0241
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.692
_diffrn_reflns_theta_max         31.116
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4861
_reflns_number_gt                4185
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0638P)²+0.2536P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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         4861
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0493
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1234
_refine_ls_wR_factor_gt          0.1187
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.79405(15) -0.39957(13) 1.08858(8) 0.01845(19) Uani 1 1 d . . . . .
H1 H 0.798276 -0.490979 1.142567 0.022 Uiso 1 1 calc R U . . .
C2 C 0.75590(13) -0.13850(12) 0.95202(7) 0.01259(17) Uani 1 1 d . . . . .
C3 C 0.72522(12) 0.01680(11) 0.87691(7) 0.01210(16) Uani 1 1 d . . . . .
C4 C 0.78499(14) 0.15336(12) 0.88442(7) 0.01464(17) Uani 1 1 d . . . . .
H4 H 0.840569 0.148413 0.939797 0.018 Uiso 1 1 calc R U . . .
C5 C 0.76345(14) 0.29654(12) 0.81111(7) 0.01502(17) Uani 1 1 d . . . . .
H5 H 0.805221 0.388664 0.816086 0.018 Uiso 1 1 calc R U . . .
C6 C 0.68028(13) 0.30449(12) 0.73021(7) 0.01285(17) Uani 1 1 d . . . . .
C7 C 0.61586(13) 0.17082(12) 0.72405(7) 0.01456(17) Uani 1 1 d . . . . .
H7 H 0.556625 0.177899 0.669901 0.017 Uiso 1 1 calc R U . . .
C8 C 0.63807(13) 0.02724(12) 0.79691(7) 0.01414(17) Uani 1 1 d . . . . .
H8 H 0.594217 -0.063735 0.792477 0.017 Uiso 1 1 calc R U . . .
C9 C 0.48996(13) 0.74170(12) 0.59079(7) 0.01391(17) Uani 1 1 d . . . . .
C10 C 0.35477(14) 0.90906(13) 0.60759(8) 0.01785(19) Uani 1 1 d . . . . .
H10 H 0.330090 0.991281 0.549938 0.021 Uiso 1 1 calc R U . . .
C11 C 0.25413(15) 0.95763(13) 0.70943(8) 0.01930(19) Uani 1 1 d . . . . .
H11 H 0.159289 1.072018 0.721326 0.023 Uiso 1 1 calc R U . . .
C12 C 0.29403(14) 0.83704(13) 0.79322(8) 0.01695(18) Uani 1 1 d . . . . .
H12 H 0.225847 0.869021 0.862647 0.020 Uiso 1 1 calc R U . . .
C13 C 0.43368(13) 0.66943(12) 0.77573(7) 0.01450(17) Uani 1 1 d . . . . .
H13 H 0.463018 0.589566 0.833615 0.017 Uiso 1 1 calc R U . . .
C14 C 0.53098(13) 0.61742(11) 0.67423(7) 0.01221(16) Uani 1 1 d . . . . .
C15 C 0.77445(13) 0.41346(12) 0.54893(7) 0.01257(16) Uani 1 1 d . . . . .
C16 C 0.92929(14) 0.25684(12) 0.52314(7) 0.01574(18) Uani 1 1 d . . . . .
H16 H 0.961426 0.167005 0.576370 0.019 Uiso 1 1 calc R U . . .
C17 C 1.03722(14) 0.23061(12) 0.42041(7) 0.01703(18) Uani 1 1 d . . . . .
H17 H 1.141306 0.122613 0.403970 0.020 Uiso 1 1 calc R U . . .
C18 C 0.99370(15) 0.36170(13) 0.34142(7) 0.01830(19) Uani 1 1 d . . . . .
H18 H 1.067789 0.343452 0.271354 0.022 Uiso 1 1 calc R U . . .
C19 C 0.84003(14) 0.52037(13) 0.36615(7) 0.01648(18) Uani 1 1 d . . . . .
H19 H 0.809751 0.611274 0.313184 0.020 Uiso 1 1 calc R U . . .
C20 C 0.73248(13) 0.54364(12) 0.46860(7) 0.01315(17) Uani 1 1 d . . . . .
N1 N 0.66407(12) 0.44648(10) 0.65196(6) 0.01484(16) Uani 1 1 d . . . . .
N2 N 0.84603(13) -0.14478(11) 1.02531(6) 0.01772(17) Uani 1 1 d . . . . .
N3 N 0.86492(13) -0.28007(12) 1.09593(7) 0.01939(18) Uani 1 1 d . . . . .
N4 N 0.71718(14) -0.40294(12) 1.01203(7) 0.02182(19) Uani 1 1 d . . . . .
N5 N 0.69819(14) -0.26834(12) 0.94071(7) 0.02068(18) Uani 1 1 d . . . . .
O1 O 0.57912(11) 0.70179(9) 0.48750(5) 0.01917(16) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N3 1.3271(13) . ?
C1 N4 1.3377(13) . ?
C1 H1 0.9500 . ?
C2 N2 1.3478(12) . ?
C2 N5 1.3512(12) . ?
C2 C3 1.4751(12) . ?
C3 C4 1.3976(12) . ?
C3 C8 1.4017(12) . ?
C4 C5 1.3915(12) . ?
C4 H4 0.9500 . ?
C5 C6 1.3966(12) . ?
C5 H5 0.9500 . ?
C6 C7 1.3944(13) . ?
C6 N1 1.4258(11) . ?
C7 C8 1.3902(12) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
C9 C10 1.3794(13) . ?
C9 O1 1.3857(11) . ?
C9 C14 1.4040(12) . ?
C10 C11 1.3973(14) . ?
C10 H10 0.9500 . ?
C11 C12 1.3907(14) . ?
C11 H11 0.9500 . ?
C12 C13 1.3939(13) . ?
C12 H12 0.9500 . ?
C13 C14 1.3961(12) . ?
C13 H13 0.9500 . ?
C14 N1 1.4058(11) . ?
C15 C16 1.3946(13) . ?
C15 C20 1.4005(12) . ?
C15 N1 1.4050(11) . ?
C16 C17 1.3910(13) . ?
C16 H16 0.9500 . ?
C17 C18 1.3940(13) . ?
C17 H17 0.9500 . ?
C18 C19 1.3993(14) . ?
C18 H18 0.9500 . ?
C19 C20 1.3852(12) . ?
C19 H19 0.9500 . ?
C20 O1 1.3866(11) . ?
N2 N3 1.3258(11) . ?
N4 N5 1.3277(11) . ?

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
N3 C1 N4 125.90(9) . . ?
N3 C1 H1 117.1 . . ?
N4 C1 H1 117.1 . . ?
N2 C2 N5 124.11(8) . . ?
N2 C2 C3 117.84(8) . . ?
N5 C2 C3 118.00(8) . . ?
C4 C3 C8 119.65(8) . . ?
C4 C3 C2 120.15(8) . . ?
C8 C3 C2 120.20(8) . . ?
C5 C4 C3 120.28(8) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 119.84(8) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C7 C6 C5 120.05(8) . . ?
C7 C6 N1 119.30(8) . . ?
C5 C6 N1 120.64(8) . . ?
C8 C7 C6 120.19(8) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C7 C8 C3 119.95(8) . . ?
C7 C8 H8 120.0 . . ?
C3 C8 H8 120.0 . . ?
C10 C9 O1 116.51(8) . . ?
C10 C9 C14 121.49(8) . . ?
O1 C9 C14 121.99(8) . . ?
C9 C10 C11 119.98(9) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C12 C11 C10 119.42(9) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C13 120.26(9) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C14 120.85(8) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C13 C14 C9 117.95(8) . . ?
C13 C14 N1 123.20(8) . . ?
C9 C14 N1 118.84(8) . . ?
C16 C15 C20 118.02(8) . . ?
C16 C15 N1 122.55(8) . . ?
C20 C15 N1 119.40(8) . . ?
C17 C16 C15 120.78(8) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C18 120.46(9) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C17 C18 C19 119.48(9) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C20 C19 C18 119.37(8) . . ?
C20 C19 H19 120.3 . . ?
C18 C19 H19 120.3 . . ?
C19 C20 O1 116.57(8) . . ?
C19 C20 C15 121.88(8) . . ?
O1 C20 C15 121.55(8) . . ?
C15 N1 C14 119.00(7) . . ?
C15 N1 C6 119.61(7) . . ?
C14 N1 C6 121.27(7) . . ?
N3 N2 C2 117.72(8) . . ?
N2 N3 C1 117.27(8) . . ?
N5 N4 C1 117.14(8) . . ?
N4 N5 C2 117.44(8) . . ?
C9 O1 C20 117.61(7) . . ?

_refine_diff_density_max         0.555
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.055



