# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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data_DCM-2
_database_code_depnum_ccdc_archive 'CCDC 2120494'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2021-11-10 deposited with the CCDC.	2022-02-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        
(E)-2-(2-(4-((2-azidoethyl)(methyl)amino)styryl)-6-(tert-butyl)-4H-pyran-4-ylidene)malononitrile
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H24 N6 O'
_chemical_formula_sum            'C23 H24 N6 O'
_chemical_formula_weight         400.48

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'

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

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

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

_cell_length_a                   7.3618(4)
_cell_length_b                   9.7239(5)
_cell_length_c                   16.0733(8)
_cell_angle_alpha                86.088(4)
_cell_angle_beta                 83.182(4)
_cell_angle_gamma                74.189(4)
_cell_volume                     1098.48(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    8505
_cell_measurement_theta_min      3.0130
_cell_measurement_theta_max      29.4050

_exptl_crystal_description       platelet
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_F_000             424
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.03
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.27002
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.96a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_detector                 'Dectris PILATUS3 R 200K-A area detector'
_diffrn_detector_area_resol_mean 5.811
_diffrn_detector_type            'Hybrid Photon Counting area detector'

_diffrn_measurement_device       'kappa gonio four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB PRO'
_diffrn_measurement_method       'ω scans'

_diffrn_radiation_collimation    
'Rigaku Integrated Confocal MaxFlux double bounce multi-layer mirror optics'
_diffrn_radiation_monochromator  none
_diffrn_radiation_probe          x-ray

_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Rigaku micromax 003'
_diffrn_reflns_number            22812
_diffrn_reflns_av_unetI/netI     0.0200
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_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         2.483
_diffrn_reflns_theta_max         26.022
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4312
_reflns_number_gt                3638
_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       'CrysAlisPro 1.171.41.96a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.96a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.96a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_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)+(0.0688P)²+0.2196P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4310
_refine_ls_number_parameters     275
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0527
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1314
_refine_ls_wR_factor_gt          0.1262
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.9947(3) -0.09334(16) 0.59802(10) 0.0888(6) Uani 1 1 d . . . . .
C1 C 0.68618(19) 0.36860(14) 0.71974(8) 0.0405(3) Uani 1 1 d . . . . .
H1 H 0.657619 0.349033 0.776480 0.049 Uiso 1 1 calc R U . . .
N2 N 0.8011(3) 0.03830(16) 0.85163(9) 0.0784(5) Uani 1 1 d . . . . .
C2 C 0.63747(19) 0.50381(14) 0.68977(8) 0.0407(3) Uani 1 1 d . . . . .
O3 O 0.67612(15) 0.53628(9) 0.60659(6) 0.0463(3) Uani 1 1 d . . . . .
N3 N 0.80821(18) 0.83147(12) 0.10220(7) 0.0475(3) Uani 1 1 d . . . . .
C4 C 0.76021(19) 0.42989(14) 0.55247(8) 0.0403(3) Uani 1 1 d . . . . .
N4 N 0.7897(2) 0.60577(15) -0.00899(10) 0.0667(4) Uani 1 1 d . . . . .
C5 C 0.81214(19) 0.29199(14) 0.57974(8) 0.0406(3) Uani 1 1 d . . . . .
H5 H 0.868745 0.221280 0.541502 0.049 Uiso 1 1 calc R U . . .
N5 N 0.6228(3) 0.65388(15) 0.01451(9) 0.0642(4) Uani 1 1 d . . . . .
C6 C 0.78169(18) 0.25306(13) 0.66605(8) 0.0377(3) Uani 1 1 d . . . . .
N6 N 0.4655(3) 0.6836(2) 0.03589(13) 0.0937(6) Uani 1 1 d . . . . .
C7 C 0.8400(2) 0.11288(14) 0.69597(8) 0.0435(3) Uani 1 1 d . . . . .
C8 C 0.5445(2) 0.63848(15) 0.73736(9) 0.0499(4) Uani 1 1 d . . . . .
C9 C 0.7875(2) 0.47926(15) 0.46654(8) 0.0439(3) Uani 1 1 d . . . . .
H9 H 0.853005 0.411571 0.427818 0.053 Uiso 1 1 calc R U . . .
C10 C 0.4732(3) 0.5998(2) 0.82707(11) 0.0751(5) Uani 1 1 d . . . . .
H10A H 0.408326 0.685762 0.855750 0.113 Uiso 1 1 calc R U . . .
H10B H 0.579039 0.547992 0.856215 0.113 Uiso 1 1 calc R U . . .
H10C H 0.387416 0.541518 0.825412 0.113 Uiso 1 1 calc R U . . .
C12 C 0.3772(3) 0.72866(19) 0.69385(13) 0.0737(5) Uani 1 1 d . . . . .
H12A H 0.313605 0.810517 0.726361 0.111 Uiso 1 1 calc R U . . .
H12B H 0.290415 0.672645 0.688498 0.111 Uiso 1 1 calc R U . . .
H12C H 0.421943 0.759805 0.639178 0.111 Uiso 1 1 calc R U . . .
C11 C 0.6910(3) 0.72142(19) 0.74055(14) 0.0759(5) Uani 1 1 d . . . . .
H11A H 0.633558 0.807810 0.769990 0.114 Uiso 1 1 calc R U . . .
H11B H 0.737424 0.744871 0.684501 0.114 Uiso 1 1 calc R U . . .
H11C H 0.794643 0.663977 0.769167 0.114 Uiso 1 1 calc R U . . .
C13 C 0.7264(2) 0.61432(15) 0.43797(8) 0.0447(3) Uani 1 1 d . . . . .
H13 H 0.661274 0.681142 0.477251 0.054 Uiso 1 1 calc R U . . .
C14 C 0.75106(19) 0.66779(14) 0.35172(8) 0.0412(3) Uani 1 1 d . . . . .
C15 C 0.8579(2) 0.58313(14) 0.28731(8) 0.0455(3) Uani 1 1 d . . . . .
H15 H 0.918040 0.487984 0.299796 0.055 Uiso 1 1 calc R U . . .
C16 C 0.8778(2) 0.63476(14) 0.20609(8) 0.0456(3) Uani 1 1 d . . . . .
H16 H 0.950135 0.573959 0.165122 0.055 Uiso 1 1 calc R U . . .
C17 C 0.79116(19) 0.77759(14) 0.18370(8) 0.0405(3) Uani 1 1 d . . . . .
C18 C 0.6823(2) 0.86295(15) 0.24802(9) 0.0489(3) Uani 1 1 d . . . . .
H18 H 0.620544 0.957794 0.235640 0.059 Uiso 1 1 calc R U . . .
C19 C 0.6647(2) 0.80938(15) 0.32942(9) 0.0488(3) Uani 1 1 d . . . . .
H19 H 0.592888 0.869750 0.370684 0.059 Uiso 1 1 calc R U . . .
C20 C 0.7113(3) 0.97949(17) 0.08269(10) 0.0628(4) Uani 1 1 d . . . . .
H20A H 0.727582 0.998069 0.023228 0.094 Uiso 1 1 calc R U . . .
H20B H 0.763842 1.041552 0.110681 0.094 Uiso 1 1 calc R U . . .
H20C H 0.578508 0.996649 0.101283 0.094 Uiso 1 1 calc R U . . .
C21 C 0.9627(2) 0.76443(17) 0.04091(9) 0.0532(4) Uani 1 1 d . . . . .
H21A H 1.046826 0.683481 0.067770 0.064 Uiso 1 1 calc R U . . .
H21B H 1.035014 0.832339 0.021479 0.064 Uiso 1 1 calc R U . . .
C22 C 0.8957(3) 0.71382(18) -0.03347(9) 0.0616(4) Uani 1 1 d . . . . .
H22A H 0.814698 0.795020 -0.061511 0.074 Uiso 1 1 calc R U . . .
H22B H 1.004527 0.672973 -0.072855 0.074 Uiso 1 1 calc R U . . .
C23 C 0.9270(3) -0.00094(15) 0.64127(9) 0.0560(4) Uani 1 1 d . . . . .
C24 C 0.8178(2) 0.07267(15) 0.78245(9) 0.0521(4) 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
N1 C23 1.139(2) . ?
C1 C2 1.3367(18) . ?
C1 C6 1.4349(18) . ?
C1 H1 0.9300 . ?
N2 C24 1.1412(19) . ?
C2 O3 1.3672(15) . ?
C2 C8 1.5141(18) . ?
O3 C4 1.3624(15) . ?
N3 C17 1.3818(16) . ?
N3 C21 1.4514(19) . ?
N3 C20 1.4529(18) . ?
C4 C5 1.3478(18) . ?
C4 C9 1.4404(17) . ?
N4 N5 1.213(2) . ?
N4 C22 1.478(2) . ?
C5 C6 1.4208(17) . ?
C5 H5 0.9300 . ?
N5 N6 1.131(2) . ?
C6 C7 1.3836(18) . ?
C7 C24 1.4207(18) . ?
C7 C23 1.422(2) . ?
C8 C12 1.519(2) . ?
C8 C11 1.520(2) . ?
C8 C10 1.533(2) . ?
C9 C13 1.335(2) . ?
C9 H9 0.9300 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C13 C14 1.4557(18) . ?
C13 H13 0.9300 . ?
C14 C19 1.3921(19) . ?
C14 C15 1.3922(19) . ?
C15 C16 1.3722(19) . ?
C15 H15 0.9300 . ?
C16 C17 1.4032(19) . ?
C16 H16 0.9300 . ?
C17 C18 1.3992(19) . ?
C18 C19 1.3796(19) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.506(2) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?

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 121.28(11) . . ?
C2 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?
C1 C2 O3 120.89(11) . . ?
C1 C2 C8 128.42(12) . . ?
O3 C2 C8 110.65(11) . . ?
C4 O3 C2 120.08(10) . . ?
C17 N3 C21 122.02(11) . . ?
C17 N3 C20 119.51(11) . . ?
C21 N3 C20 115.56(11) . . ?
C5 C4 O3 121.16(11) . . ?
C5 C4 C9 124.77(12) . . ?
O3 C4 C9 114.07(11) . . ?
N5 N4 C22 115.12(14) . . ?
C4 C5 C6 120.97(12) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
N6 N5 N4 172.3(2) . . ?
C7 C6 C5 122.03(12) . . ?
C7 C6 C1 122.45(11) . . ?
C5 C6 C1 115.53(11) . . ?
C6 C7 C24 122.83(12) . . ?
C6 C7 C23 121.59(12) . . ?
C24 C7 C23 115.57(12) . . ?
C2 C8 C12 109.87(12) . . ?
C2 C8 C11 108.54(13) . . ?
C12 C8 C11 110.34(15) . . ?
C2 C8 C10 110.09(12) . . ?
C12 C8 C10 108.89(15) . . ?
C11 C8 C10 109.10(15) . . ?
C13 C9 C4 125.30(13) . . ?
C13 C9 H9 117.3 . . ?
C4 C9 H9 117.3 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C13 C14 126.74(13) . . ?
C9 C13 H13 116.6 . . ?
C14 C13 H13 116.6 . . ?
C19 C14 C15 116.25(12) . . ?
C19 C14 C13 120.53(12) . . ?
C15 C14 C13 123.22(12) . . ?
C16 C15 C14 122.49(12) . . ?
C16 C15 H15 118.8 . . ?
C14 C15 H15 118.8 . . ?
C15 C16 C17 121.23(12) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
N3 C17 C18 121.26(12) . . ?
N3 C17 C16 122.17(12) . . ?
C18 C17 C16 116.56(12) . . ?
C19 C18 C17 121.39(12) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C18 C19 C14 122.07(13) . . ?
C18 C19 H19 119.0 . . ?
C14 C19 H19 119.0 . . ?
N3 C20 H20A 109.5 . . ?
N3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N3 C21 C22 113.03(14) . . ?
N3 C21 H21A 109.0 . . ?
C22 C21 H21A 109.0 . . ?
N3 C21 H21B 109.0 . . ?
C22 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
N4 C22 C21 112.11(13) . . ?
N4 C22 H22A 109.2 . . ?
C21 C22 H22A 109.2 . . ?
N4 C22 H22B 109.2 . . ?
C21 C22 H22B 109.2 . . ?
H22A C22 H22B 107.9 . . ?
N1 C23 C7 178.9(2) . . ?
N2 C24 C7 178.99(16) . . ?

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 O3 0.5(2) . . . . ?
C6 C1 C2 C8 -177.17(13) . . . . ?
C1 C2 O3 C4 2.00(19) . . . . ?
C8 C2 O3 C4 -179.99(12) . . . . ?
C2 O3 C4 C5 -2.07(19) . . . . ?
C2 O3 C4 C9 178.32(11) . . . . ?
O3 C4 C5 C6 -0.3(2) . . . . ?
C9 C4 C5 C6 179.24(13) . . . . ?
C4 C5 C6 C7 -177.59(13) . . . . ?
C4 C5 C6 C1 2.59(19) . . . . ?
C2 C1 C6 C7 177.52(13) . . . . ?
C2 C1 C6 C5 -2.67(19) . . . . ?
C5 C6 C7 C24 177.34(13) . . . . ?
C1 C6 C7 C24 -2.9(2) . . . . ?
C5 C6 C7 C23 -2.6(2) . . . . ?
C1 C6 C7 C23 177.20(14) . . . . ?
C1 C2 C8 C12 -131.15(17) . . . . ?
O3 C2 C8 C12 51.03(18) . . . . ?
C1 C2 C8 C11 108.12(18) . . . . ?
O3 C2 C8 C11 -69.70(16) . . . . ?
C1 C2 C8 C10 -11.2(2) . . . . ?
O3 C2 C8 C10 170.95(13) . . . . ?
C5 C4 C9 C13 175.66(14) . . . . ?
O3 C4 C9 C13 -4.8(2) . . . . ?
C4 C9 C13 C14 -179.87(13) . . . . ?
C9 C13 C14 C19 174.10(14) . . . . ?
C9 C13 C14 C15 -5.2(2) . . . . ?
C19 C14 C15 C16 -0.2(2) . . . . ?
C13 C14 C15 C16 179.17(14) . . . . ?
C14 C15 C16 C17 0.3(2) . . . . ?
C21 N3 C17 C18 159.76(14) . . . . ?
C20 N3 C17 C18 -0.1(2) . . . . ?
C21 N3 C17 C16 -21.6(2) . . . . ?
C20 N3 C17 C16 178.56(14) . . . . ?
C15 C16 C17 N3 -179.50(13) . . . . ?
C15 C16 C17 C18 -0.8(2) . . . . ?
N3 C17 C18 C19 179.87(14) . . . . ?
C16 C17 C18 C19 1.2(2) . . . . ?
C17 C18 C19 C14 -1.1(2) . . . . ?
C15 C14 C19 C18 0.5(2) . . . . ?
C13 C14 C19 C18 -178.83(14) . . . . ?
C17 N3 C21 C22 119.02(15) . . . . ?
C20 N3 C21 C22 -80.41(17) . . . . ?
N5 N4 C22 C21 83.84(19) . . . . ?
N3 C21 C22 N4 -60.68(18) . . . . ?

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
C5 H5 N1 0.93 2.60 3.494(2) 161.8 2_756 yes
C22 H22A N2 0.97 2.65 3.488(2) 145.1 1_564 yes

_refine_diff_density_max         0.168
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.033







####################################################################### 
# 
# 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_pnma
_database_code_depnum_ccdc_archive 'CCDC 2121293'
loop_
_audit_author_name
_audit_author_address
'Pascal Retailleau'
;ICSN CNRS University Paris Saclay
France
;
_audit_update_record             
;
2021-11-10 deposited with the CCDC.	2022-02-09 downloaded from the CCDC.
;

# start Validation Reply Form

_vrf_PLAT430_pnma                
;
PROBLEM: Short Inter D...A Contact  N4       ..N4     .   2.84 Ang.  
RESPONSE: This alert is no longer valid when considering disorder
of the azidoethyl on both sides of the mirror plane with half site
occupancy, and the non (full)respect of the inversion center 
between related molecules along the b direction regarding the
linear orientation of the terminal C-N3 group.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2018/3


_chemical_name_systematic        
(E)-2-(2-(4-((2-azidoethyl)(methyl)amino)styryl)-6-(tert-butyl)-4H-pyran-4-ylidene)malononitrile
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H24 N6 O'
_chemical_formula_sum            'C23 H24 N6 O'
_chemical_formula_weight         400.48

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_H-M_alt        'P n m a'
_space_group_name_Hall           '-P 2ac 2n'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'

_cell_length_a                   29.8656(17)
_cell_length_b                   7.1127(4)
_cell_length_c                   10.0461(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2134.0(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4858
_cell_measurement_theta_min      3.1740
_cell_measurement_theta_max      29.0830

_exptl_crystal_description       tab
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.13
_exptl_absorpt_coefficient_mu    0.080
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.68649
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.118a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_detector                 'Dectris PILATUS3 R 200K-A area detector'
_diffrn_detector_area_resol_mean 5.811
_diffrn_detector_type            'Hybrid Photon Counting area detector'

_diffrn_measurement_device       'kappa gonio four-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku XtaLAB PRO'
_diffrn_measurement_method       'ω scans'

_diffrn_radiation_collimation    
'Rigaku Integrated Confocal MaxFlux double bounce multi-layer mirror optics'
_diffrn_radiation_monochromator  none
_diffrn_radiation_probe          x-ray

_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Rigaku micromax 003'
_diffrn_reflns_number            13711
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.881
_diffrn_reflns_theta_max         26.019
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2283
_reflns_number_gt                1921
_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       'CrysAlisPro 1.171.41.96a (Rigaku OD, 2021)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.96a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.96a (Rigaku OD, 2021)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_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)+(0.1286P)²+0.5387P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     other
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2280
_refine_ls_number_parameters     188
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0731
_refine_ls_R_factor_gt           0.0659
_refine_ls_wR_factor_ref         0.2093
_refine_ls_wR_factor_gt          0.2012
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_restrained_S_all      1.091
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.32833(8) 0.250000 0.3873(2) 0.0438(6) Uani 1 2 d S T P . .
H1 H 0.358207 0.250000 0.413391 0.053 Uiso 1 2 calc R U P . .
N1 N 0.24012(9) 0.250000 0.7935(3) 0.0862(10) Uani 1 2 d S T P . .
N2 N 0.38263(8) 0.250000 0.7181(3) 0.0831(9) Uani 1 2 d S T P . .
C2 C 0.31819(7) 0.250000 0.2575(2) 0.0422(6) Uani 1 2 d S T P . .
N3 N 0.00919(7) 0.250000 -0.0881(2) 0.0674(8) Uani 1 2 d S T P . .
O3 O 0.27463(5) 0.250000 0.21476(15) 0.0471(5) Uani 1 2 d S T P . .
C4 C 0.24075(7) 0.250000 0.3059(2) 0.0449(6) Uani 1 2 d S T P . .
C6 C 0.29391(7) 0.250000 0.4869(2) 0.0413(5) Uani 1 2 d S T P . .
C5 C 0.24955(7) 0.250000 0.4374(2) 0.0450(6) Uani 1 2 d S T P . .
H5 H 0.225810 0.250000 0.497292 0.054 Uiso 1 2 calc R U P . .
C7 C 0.30321(8) 0.250000 0.6218(2) 0.0453(6) Uani 1 2 d S T P . .
C9 C 0.19651(8) 0.250000 0.2503(3) 0.0490(6) Uani 1 2 d S T P . .
H9 H 0.172830 0.250000 0.310414 0.059 Uiso 1 2 calc R U P . .
C8 C 0.34993(8) 0.250000 0.1405(2) 0.0477(6) Uani 1 2 d S T P . .
C10 C 0.39840(8) 0.250000 0.1895(3) 0.0644(8) Uani 1 2 d S T P . .
H10A H 0.411425 0.250000 0.112762 0.097 Uiso 1 2 d R U P . .
H10 H 0.406643 0.127275 0.234339 0.097 Uiso 1 1 d R U . . .
C12 C 0.34143(7) 0.0742(3) 0.0567(2) 0.0685(6) Uani 1 1 d . . . . .
H12A H 0.361760 0.072186 -0.017268 0.103 Uiso 1 1 calc R U . . .
H12B H 0.311184 0.075656 0.024421 0.103 Uiso 1 1 calc R U . . .
H12C H 0.346014 -0.035791 0.110464 0.103 Uiso 1 1 calc R U . . .
C24 C 0.34741(9) 0.250000 0.6732(2) 0.0554(7) Uani 1 2 d S T P . .
C23 C 0.26822(8) 0.250000 0.7178(2) 0.0540(7) Uani 1 2 d S T P . .
C14 C 0.14044(8) 0.250000 0.0677(2) 0.0465(6) Uani 1 2 d S T P . .
C13 C 0.18573(8) 0.250000 0.1208(2) 0.0481(6) Uani 1 2 d S T P . .
H13 H 0.209165 0.250000 0.059794 0.058 Uiso 1 2 calc R U P . .
C15 C 0.10252(8) 0.250000 0.1487(3) 0.0565(7) Uani 1 2 d S T P . .
H15 H 0.106257 0.250000 0.240593 0.068 Uiso 1 2 calc R U P . .
C16 C 0.05989(8) 0.250000 0.0977(3) 0.0558(7) Uani 1 2 d S T P . .
H16 H 0.035610 0.250000 0.155673 0.067 Uiso 1 2 calc R U P . .
C17 C 0.05224(8) 0.250000 -0.0394(3) 0.0510(6) Uani 1 2 d S T P . .
C18 C 0.09020(8) 0.250000 -0.1216(3) 0.0553(7) Uani 1 2 d S T P . .
H18 H 0.086552 0.250000 -0.213574 0.066 Uiso 1 2 calc R U P . .
C19 C 0.13282(8) 0.250000 -0.0689(3) 0.0515(6) Uani 1 2 d S T P . .
H19 H 0.157223 0.250000 -0.126365 0.062 Uiso 1 2 calc R U P . .
C20 C -0.02877(8) 0.250000 0.0010(3) 0.0652(8) Uani 1 2 d S T P . .
H20A H -0.053608 0.250000 -0.040802 0.098 Uiso 1 2 d R U P . .
H20B H -0.026413 0.143438 0.068489 0.098 Uiso 1 1 d R U . . .
C21 C -0.00047(13) 0.1820(6) -0.2270(4) 0.0619(11) Uani 0.5 1 d . . P . .
H21A H -0.026799 0.102211 -0.227321 0.074 Uiso 0.5 1 calc R U P . .
H21B H 0.024675 0.110229 -0.260898 0.074 Uiso 0.5 1 calc R U P . .
C22 C -0.0083(2) 0.1448(10) -0.3127(5) 0.0969(19) Uani 0.5 1 d . . P . .
H22A H 0.015098 0.053866 -0.294624 0.116 Uiso 0.5 1 calc R U P . .
H22B H -0.036649 0.088311 -0.287574 0.116 Uiso 0.5 1 calc R U P . .
N4 N -0.0090(2) 0.1833(11) -0.4515(6) 0.139(4) Uani 0.5 1 d . . P . .
N5 N 0.0286(2) 0.250000 -0.4979(5) 0.177(3) Uani 1 2 d S T P . .
N6 N 0.0604(2) 0.250000 -0.5471(6) 0.209(4) Uani 1 2 d S T P . .


_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 1.339(3) . ?
C1 C6 1.434(3) . ?
C1 H1 0.9300 . ?
N1 C23 1.133(3) . ?
N2 C24 1.145(3) . ?
C2 O3 1.370(3) . ?
C2 C8 1.510(3) . ?
N3 C17 1.376(3) . ?
N3 C20 1.444(3) . ?
N3 C21 1.505(5) . ?
N3 C21 1.505(5) 8_565 ?
O3 C4 1.365(3) . ?
C4 C5 1.347(4) . ?
C4 C9 1.435(3) . ?
C6 C7 1.383(3) . ?
C6 C5 1.415(3) . ?
C5 H5 0.9300 . ?
C7 C24 1.417(3) . ?
C7 C23 1.422(3) . ?
C9 C13 1.341(4) . ?
C9 H9 0.9300 . ?
C8 C12 1.529(2) . ?
C8 C12 1.529(2) 8_565 ?
C8 C10 1.529(4) . ?
C10 H10A 0.8630 . ?
C10 H10 1.0129 . ?
C10 H10 1.0129 8_565 ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C14 C19 1.391(3) . ?
C14 C15 1.395(3) . ?
C14 C13 1.454(3) . ?
C13 H13 0.9300 . ?
C15 C16 1.372(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.396(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.403(3) . ?
C18 C19 1.379(3) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C20 H20A 0.8521 . ?
C20 H20B 1.0197 . ?
C20 H20B 1.0197 8_565 ?
C21 C22 1.521(7) 8_565 ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 N4 1.421(8) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
N4 N4 0.949(16) 8_565 ?
N4 N5 1.306(8) . ?
N5 N6 1.069(7) . ?

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 121.2(2) . . ?
C2 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?
C1 C2 O3 121.3(2) . . ?
C1 C2 C8 128.0(2) . . ?
O3 C2 C8 110.62(19) . . ?
C17 N3 C20 120.9(2) . . ?
C17 N3 C21 120.6(2) . . ?
C20 N3 C21 115.1(2) . . ?
C17 N3 C21 120.6(2) . 8_565 ?
C20 N3 C21 115.1(2) . 8_565 ?
C21 N3 C21 37.5(3) . 8_565 ?
C4 O3 C2 119.59(18) . . ?
C5 C4 O3 120.9(2) . . ?
C5 C4 C9 124.2(2) . . ?
O3 C4 C9 114.9(2) . . ?
C7 C6 C5 122.2(2) . . ?
C7 C6 C1 122.6(2) . . ?
C5 C6 C1 115.2(2) . . ?
C4 C5 C6 121.8(2) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C6 C7 C24 122.9(2) . . ?
C6 C7 C23 121.1(2) . . ?
C24 C7 C23 116.0(2) . . ?
C13 C9 C4 126.8(2) . . ?
C13 C9 H9 116.6 . . ?
C4 C9 H9 116.6 . . ?
C2 C8 C12 108.92(14) . . ?
C2 C8 C12 108.92(14) . 8_565 ?
C12 C8 C12 109.8(2) . 8_565 ?
C2 C8 C10 110.13(19) . . ?
C12 C8 C10 109.53(14) . . ?
C12 C8 C10 109.53(14) 8_565 . ?
C8 C10 H10A 98.0 . . ?
C8 C10 H10 111.9 . . ?
H10A C10 H10 106.7 . . ?
C8 C10 H10 111.92(5) . 8_565 ?
H10A C10 H10 106.7 . 8_565 ?
H10 C10 H10 119.0 . 8_565 ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C24 C7 178.1(3) . . ?
N1 C23 C7 179.5(3) . . ?
C19 C14 C15 116.3(2) . . ?
C19 C14 C13 120.9(2) . . ?
C15 C14 C13 122.8(2) . . ?
C9 C13 C14 125.4(2) . . ?
C9 C13 H13 117.3 . . ?
C14 C13 H13 117.3 . . ?
C16 C15 C14 122.4(2) . . ?
C16 C15 H15 118.8 . . ?
C14 C15 H15 118.8 . . ?
C15 C16 C17 121.3(2) . . ?
C15 C16 H16 119.3 . . ?
C17 C16 H16 119.3 . . ?
N3 C17 C16 120.2(2) . . ?
N3 C17 C18 123.1(2) . . ?
C16 C17 C18 116.7(2) . . ?
C19 C18 C17 121.3(2) . . ?
C19 C18 H18 119.3 . . ?
C17 C18 H18 119.3 . . ?
C18 C19 C14 122.0(2) . . ?
C18 C19 H19 119.0 . . ?
C14 C19 H19 119.0 . . ?
N3 C20 H20A 112.2 . . ?
N3 C20 H20B 111.0 . . ?
H20A C20 H20B 112.8 . . ?
N3 C20 H20B 110.97(9) . 8_565 ?
H20A C20 H20B 112.8 . 8_565 ?
H20B C20 H20B 96.0 . 8_565 ?
N3 C21 C22 107.1(3) . 8_565 ?
N3 C21 H21A 110.3 . . ?
C22 C21 H21A 110.3 8_565 . ?
N3 C21 H21B 110.3 . . ?
C22 C21 H21B 110.3 8_565 . ?
H21A C21 H21B 108.5 . . ?
N4 C22 C21 113.7(5) . 8_565 ?
N4 C22 H22A 108.8 . . ?
C21 C22 H22A 108.8 8_565 . ?
N4 C22 H22B 108.8 . . ?
C21 C22 H22B 108.8 8_565 . ?
H22A C22 H22B 107.7 . . ?
N4 N4 N5 68.7(3) 8_565 . ?
N4 N4 C22 101.1(4) 8_565 . ?
N5 N4 C22 114.1(5) . . ?
N4 N4 C22 48.8(3) 8_565 8_565 ?
N5 N4 C22 91.1(5) . 8_565 ?
C22 N4 C22 52.3(5) . 8_565 ?
N6 N5 N4 158.1(4) . . ?
N6 N5 N4 158.1(4) . 8_565 ?
N4 N5 N4 42.6(7) . 8_565 ?

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 O3 0.000(0) . . . . ?
C6 C1 C2 C8 180.000(0) . . . . ?
C1 C2 O3 C4 0.000(0) . . . . ?
C8 C2 O3 C4 180.000(0) . . . . ?
C2 O3 C4 C5 0.000(0) . . . . ?
C2 O3 C4 C9 180.000(0) . . . . ?
C2 C1 C6 C7 180.000(0) . . . . ?
C2 C1 C6 C5 0.000(0) . . . . ?
O3 C4 C5 C6 0.000(0) . . . . ?
C9 C4 C5 C6 180.000(0) . . . . ?
C7 C6 C5 C4 180.000(0) . . . . ?
C1 C6 C5 C4 0.000(0) . . . . ?
C5 C6 C7 C24 180.000(0) . . . . ?
C1 C6 C7 C24 0.000(0) . . . . ?
C5 C6 C7 C23 0.000(0) . . . . ?
C1 C6 C7 C23 180.000(0) . . . . ?
C5 C4 C9 C13 180.000(0) . . . . ?
O3 C4 C9 C13 0.000(0) . . . . ?
C1 C2 C8 C12 120.13(15) . . . . ?
O3 C2 C8 C12 -59.87(15) . . . . ?
C1 C2 C8 C12 -120.13(15) . . . 8_565 ?
O3 C2 C8 C12 59.87(15) . . . 8_565 ?
C1 C2 C8 C10 0.000(0) . . . . ?
O3 C2 C8 C10 180.0 . . . . ?
C4 C9 C13 C14 180.000(0) . . . . ?
C19 C14 C13 C9 180.000(0) . . . . ?
C15 C14 C13 C9 0.000(0) . . . . ?
C19 C14 C15 C16 0.0 . . . . ?
C13 C14 C15 C16 180.0 . . . . ?
C14 C15 C16 C17 0.000(0) . . . . ?
C20 N3 C17 C16 0.0 . . . . ?
C21 N3 C17 C16 -158.1(2) . . . . ?
C21 N3 C17 C16 158.1(2) 8_565 . . . ?
C20 N3 C17 C18 180.0 . . . . ?
C21 N3 C17 C18 21.9(2) . . . . ?
C21 N3 C17 C18 -21.9(2) 8_565 . . . ?
C15 C16 C17 N3 180.0 . . . . ?
C15 C16 C17 C18 0.0 . . . . ?
N3 C17 C18 C19 180.0 . . . . ?
C16 C17 C18 C19 0.000(0) . . . . ?
C17 C18 C19 C14 0.0 . . . . ?
C15 C14 C19 C18 0.0 . . . . ?
C13 C14 C19 C18 180.0 . . . . ?
C17 N3 C21 C22 -103.8(3) . . . 8_565 ?
C20 N3 C21 C22 96.9(3) . . . 8_565 ?
C21 N3 C21 C22 -2.2(4) 8_565 . . 8_565 ?
C21 C22 N4 N4 -9.2(5) 8_565 . . 8_565 ?
C21 C22 N4 N5 62.3(8) 8_565 . . . ?
C21 C22 N4 C22 -9.2(5) 8_565 . . 8_565 ?
N4 N4 N5 N6 -166.4(19) 8_565 . . . ?
C22 N4 N5 N6 100.6(18) . . . . ?
C22 N4 N5 N6 149.2(18) 8_565 . . . ?
C22 N4 N5 N4 -93.0(6) . . . 8_565 ?
C22 N4 N5 N4 -44.3(3) 8_565 . . 8_565 ?

_refine_diff_density_max         0.724
_refine_diff_density_min         -0.510
_refine_diff_density_rms         0.088


