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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_KA555_0m
_database_code_depnum_ccdc_archive 'CCDC 1887445'
loop_
_audit_author_name
_audit_author_address
'Jagadeesh Babu Nanubolu'
;CSIR-Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2018-12-27 deposited with the CCDC.	2019-08-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
N-(3-(6,7-dihydro-5H-[1,2,3]triazolo[5',1':3,4][1,4]diazepino[1,2-a]indole-1-carbonyl)phenyl)acetamide
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H19 N5 O2'
_chemical_formula_sum            'C22 H19 N5 O2'
_chemical_formula_weight         385.42

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.4652(12)
_cell_length_b                   15.665(3)
_cell_length_c                   8.435(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.931(7)
_cell_angle_gamma                90
_cell_volume                     1910.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9898
_cell_measurement_theta_min      2.617
_cell_measurement_theta_max      29.324

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6086
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   Microfocus
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            34927
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.600
_diffrn_reflns_theta_max         27.500
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4384
_reflns_number_gt                3176
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.034(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4384
_refine_ls_number_parameters     296
_refine_ls_number_restraints     72
_refine_ls_R_factor_all          0.0772
_refine_ls_R_factor_gt           0.0533
_refine_ls_wR_factor_ref         0.1703
_refine_ls_wR_factor_gt          0.1497
_refine_ls_goodness_of_fit_ref   1.172
_refine_ls_restrained_S_all      1.164
_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
O1 O 0.98337(10) 0.62309(14) -0.1014(2) 0.0942(7) Uani 1 1 d . . . . .
O2 O 0.55289(8) 0.67056(10) 0.23046(15) 0.0619(4) Uani 1 1 d . . . . .
N1 N 0.65699(10) 0.63808(10) 0.61324(18) 0.0512(4) Uani 1 1 d . . . . .
N2 N 0.61798(12) 0.63351(12) 0.74961(19) 0.0612(5) Uani 1 1 d . . . . .
N3 N 0.52537(11) 0.62512(10) 0.72096(16) 0.0505(4) Uani 1 1 d . . . . .
N4 N 0.33610(9) 0.65437(8) 0.56613(15) 0.0381(3) Uani 1 1 d . . . . .
N5 N 0.82824(10) 0.63928(10) -0.10360(17) 0.0451(4) Uani 1 1 d . . . . .
C1 C 0.4551(4) 0.5945(5) 0.8408(6) 0.0524(15) Uani 0.512(11) 1 d . U P A 1
H1A H 0.428186 0.540676 0.805940 0.063 Uiso 0.512(11) 1 calc R U P A 1
H1B H 0.485718 0.585731 0.943565 0.063 Uiso 0.512(11) 1 calc R U P A 1
C2 C 0.3792(9) 0.6621(7) 0.8537(13) 0.063(2) Uani 0.512(11) 1 d . U P A 1
H2A H 0.326492 0.635309 0.901716 0.076 Uiso 0.512(11) 1 calc R U P A 1
H2B H 0.401805 0.705860 0.926532 0.076 Uiso 0.512(11) 1 calc R U P A 1
C3 C 0.3453(7) 0.7052(6) 0.7053(12) 0.0426(15) Uani 0.512(11) 1 d . U P A 1
H3A H 0.285426 0.730165 0.725048 0.051 Uiso 0.512(11) 1 calc R U P A 1
H3B H 0.387231 0.751774 0.683748 0.051 Uiso 0.512(11) 1 calc R U P A 1
C1D C 0.4791(4) 0.6378(6) 0.8707(5) 0.0612(17) Uani 0.488(11) 1 d . U P A 2
H1C H 0.494762 0.693797 0.912812 0.073 Uiso 0.488(11) 1 calc R U P A 2
H1D H 0.501018 0.595476 0.947012 0.073 Uiso 0.488(11) 1 calc R U P A 2
C2D C 0.3744(9) 0.6306(6) 0.8491(12) 0.054(2) Uani 0.488(11) 1 d . U P A 2
H2C H 0.359357 0.572416 0.818540 0.065 Uiso 0.488(11) 1 calc R U P A 2
H2D H 0.347060 0.641101 0.950726 0.065 Uiso 0.488(11) 1 calc R U P A 2
C3D C 0.3325(10) 0.6869(9) 0.7349(16) 0.073(3) Uani 0.488(11) 1 d . U P A 2
H3C H 0.363556 0.741773 0.741675 0.088 Uiso 0.488(11) 1 calc R U P A 2
H3D H 0.268432 0.695760 0.760880 0.088 Uiso 0.488(11) 1 calc R U P A 2
C4 C 0.25877(11) 0.64359(10) 0.46656(18) 0.0377(4) Uani 1 1 d . . . . .
C5 C 0.16839(12) 0.67331(14) 0.4799(2) 0.0575(5) Uani 1 1 d . . . . .
H5 H 0.150858 0.704112 0.568235 0.069 Uiso 1 1 calc R U . . .
C6 C 0.10610(13) 0.65528(17) 0.3572(3) 0.0715(7) Uani 1 1 d . . . . .
H6 H 0.045586 0.674784 0.362985 0.086 Uiso 1 1 calc R U . . .
C7 C 0.13116(14) 0.60870(17) 0.2247(3) 0.0694(6) Uani 1 1 d . . . . .
H7 H 0.087081 0.597622 0.144566 0.083 Uiso 1 1 calc R U . . .
C8 C 0.21933(13) 0.57892(12) 0.2103(2) 0.0532(5) Uani 1 1 d . . . . .
H8 H 0.235354 0.547470 0.121822 0.064 Uiso 1 1 calc R U . . .
C9 C 0.28569(11) 0.59699(10) 0.33280(17) 0.0367(4) Uani 1 1 d . . . . .
C10 C 0.38232(11) 0.58140(10) 0.35360(17) 0.0372(4) Uani 1 1 d . . . . .
H10 H 0.419230 0.552003 0.283806 0.045 Uiso 1 1 calc R U . . .
C11 C 0.41116(10) 0.61735(9) 0.49444(17) 0.0341(3) Uani 1 1 d . . . . .
C12 C 0.50469(11) 0.62531(9) 0.56283(17) 0.0360(4) Uani 1 1 d . . . . .
C13 C 0.59016(11) 0.63331(10) 0.49456(18) 0.0376(4) Uani 1 1 d . . . . .
C14 C 0.61127(11) 0.64123(10) 0.32392(19) 0.0399(4) Uani 1 1 d . . . . .
C15 C 0.70318(10) 0.61231(10) 0.26748(18) 0.0374(4) Uani 1 1 d . . . . .
C16 C 0.76123(12) 0.55602(11) 0.3531(2) 0.0465(4) Uani 1 1 d . . . . .
H16 H 0.746065 0.538073 0.454021 0.056 Uiso 1 1 calc R U . . .
C17 C 0.84143(12) 0.52747(12) 0.2855(2) 0.0532(5) Uani 1 1 d . . . . .
H17 H 0.879615 0.489496 0.341544 0.064 Uiso 1 1 calc R U . . .
C18 C 0.86592(11) 0.55409(11) 0.1370(2) 0.0473(4) Uani 1 1 d . . . . .
H18 H 0.920160 0.534214 0.093786 0.057 Uiso 1 1 calc R U . . .
C19 C 0.80888(10) 0.61119(10) 0.05137(18) 0.0381(4) Uani 1 1 d . . . . .
C20 C 0.72759(11) 0.63934(10) 0.11676(19) 0.0387(4) Uani 1 1 d . . . . .
H20 H 0.688994 0.676544 0.059692 0.046 Uiso 1 1 calc R U . . .
C21 C 0.91182(12) 0.64323(12) -0.1710(2) 0.0495(5) Uani 1 1 d . . . . .
C22 C 0.90970(15) 0.67456(17) -0.3391(2) 0.0694(6) Uani 1 1 d . . . . .
H22A H 0.932055 0.630542 -0.407118 0.104 Uiso 1 1 calc R U . . .
H22B H 0.948327 0.724134 -0.346570 0.104 Uiso 1 1 calc R U . . .
H22C H 0.847364 0.689057 -0.371231 0.104 Uiso 1 1 calc R U . . .
H5N H 0.7794(18) 0.6589(14) -0.154(3) 0.073(7) Uiso 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
O1 C21 1.214(2) . ?
O2 C14 1.2251(19) . ?
N1 N2 1.300(2) . ?
N1 C13 1.370(2) . ?
N2 N3 1.360(2) . ?
N3 C12 1.357(2) . ?
N3 C1D 1.463(5) . ?
N3 C1 1.534(5) . ?
N4 C4 1.386(2) . ?
N4 C11 1.3875(19) . ?
N4 C3 1.421(12) . ?
N4 C3D 1.515(14) . ?
N5 C21 1.355(2) . ?
N5 C19 1.416(2) . ?
N5 H5N 0.87(2) . ?
C1 C2 1.533(13) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.491(13) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C1D C2D 1.523(15) . ?
C1D H1C 0.9700 . ?
C1D H1D 0.9700 . ?
C2D C3D 1.426(15) . ?
C2D H2C 0.9700 . ?
C2D H2D 0.9700 . ?
C3D H3C 0.9700 . ?
C3D H3D 0.9700 . ?
C4 C5 1.396(2) . ?
C4 C9 1.410(2) . ?
C5 C6 1.379(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.392(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.367(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.415(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.424(2) . ?
C10 C11 1.367(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.458(2) . ?
C12 C13 1.387(2) . ?
C13 C14 1.487(2) . ?
C14 C15 1.497(2) . ?
C15 C20 1.397(2) . ?
C15 C16 1.401(2) . ?
C16 C17 1.384(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.378(2) . ?
C17 H17 0.9300 . ?
C18 C19 1.401(2) . ?
C18 H18 0.9300 . ?
C19 C20 1.388(2) . ?
C20 H20 0.9300 . ?
C21 C22 1.500(3) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?

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
N2 N1 C13 109.07(14) . . ?
N1 N2 N3 107.61(13) . . ?
C12 N3 N2 110.96(15) . . ?
C12 N3 C1D 139.1(3) . . ?
N2 N3 C1D 108.1(3) . . ?
C12 N3 C1 121.3(3) . . ?
N2 N3 C1 125.7(3) . . ?
C4 N4 C11 108.20(12) . . ?
C4 N4 C3 128.3(5) . . ?
C11 N4 C3 122.8(5) . . ?
C4 N4 C3D 123.9(6) . . ?
C11 N4 C3D 127.0(6) . . ?
C21 N5 C19 127.49(15) . . ?
C21 N5 H5N 119.9(16) . . ?
C19 N5 H5N 112.5(16) . . ?
C2 C1 N3 108.9(6) . . ?
C2 C1 H1A 109.9 . . ?
N3 C1 H1A 109.9 . . ?
C2 C1 H1B 109.9 . . ?
N3 C1 H1B 109.9 . . ?
H1A C1 H1B 108.3 . . ?
C3 C2 C1 118.0(9) . . ?
C3 C2 H2A 107.8 . . ?
C1 C2 H2A 107.8 . . ?
C3 C2 H2B 107.8 . . ?
C1 C2 H2B 107.8 . . ?
H2A C2 H2B 107.2 . . ?
N4 C3 C2 117.3(8) . . ?
N4 C3 H3A 108.0 . . ?
C2 C3 H3A 108.0 . . ?
N4 C3 H3B 108.0 . . ?
C2 C3 H3B 108.0 . . ?
H3A C3 H3B 107.2 . . ?
N3 C1D C2D 111.6(6) . . ?
N3 C1D H1C 109.3 . . ?
C2D C1D H1C 109.3 . . ?
N3 C1D H1D 109.3 . . ?
C2D C1D H1D 109.3 . . ?
H1C C1D H1D 108.0 . . ?
C3D C2D C1D 115.6(8) . . ?
C3D C2D H2C 108.4 . . ?
C1D C2D H2C 108.4 . . ?
C3D C2D H2D 108.4 . . ?
C1D C2D H2D 108.4 . . ?
H2C C2D H2D 107.4 . . ?
C2D C3D N4 113.5(10) . . ?
C2D C3D H3C 108.9 . . ?
N4 C3D H3C 108.9 . . ?
C2D C3D H3D 108.9 . . ?
N4 C3D H3D 108.9 . . ?
H3C C3D H3D 107.7 . . ?
N4 C4 C5 130.49(16) . . ?
N4 C4 C9 108.00(13) . . ?
C5 C4 C9 121.47(16) . . ?
C6 C5 C4 117.5(2) . . ?
C6 C5 H5 121.3 . . ?
C4 C5 H5 121.3 . . ?
C5 C6 C7 121.91(19) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 H6 119.0 . . ?
C8 C7 C6 121.27(18) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C9 118.59(19) . . ?
C7 C8 H8 120.7 . . ?
C9 C8 H8 120.7 . . ?
C4 C9 C8 119.29(16) . . ?
C4 C9 C10 106.66(13) . . ?
C8 C9 C10 133.99(16) . . ?
C11 C10 C9 107.82(13) . . ?
C11 C10 H10 126.1 . . ?
C9 C10 H10 126.1 . . ?
C10 C11 N4 109.30(13) . . ?
C10 C11 C12 129.12(14) . . ?
N4 C11 C12 121.41(13) . . ?
N3 C12 C13 103.78(14) . . ?
N3 C12 C11 124.02(15) . . ?
C13 C12 C11 132.19(14) . . ?
N1 C13 C12 108.57(14) . . ?
N1 C13 C14 122.68(14) . . ?
C12 C13 C14 128.65(14) . . ?
O2 C14 C13 119.65(14) . . ?
O2 C14 C15 120.60(15) . . ?
C13 C14 C15 119.75(14) . . ?
C20 C15 C16 119.63(15) . . ?
C20 C15 C14 116.87(14) . . ?
C16 C15 C14 123.35(14) . . ?
C17 C16 C15 119.17(16) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C18 C17 C16 121.43(15) . . ?
C18 C17 H17 119.3 . . ?
C16 C17 H17 119.3 . . ?
C17 C18 C19 119.81(15) . . ?
C17 C18 H18 120.1 . . ?
C19 C18 H18 120.1 . . ?
C20 C19 C18 119.35(15) . . ?
C20 C19 N5 117.69(14) . . ?
C18 C19 N5 122.90(14) . . ?
C19 C20 C15 120.60(14) . . ?
C19 C20 H20 119.7 . . ?
C15 C20 H20 119.7 . . ?
O1 C21 N5 122.91(18) . . ?
O1 C21 C22 122.15(18) . . ?
N5 C21 C22 114.94(16) . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?

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
C13 N1 N2 N3 0.42(19) . . . . ?
N1 N2 N3 C12 -0.7(2) . . . . ?
N1 N2 N3 C1D -168.3(4) . . . . ?
N1 N2 N3 C1 163.1(4) . . . . ?
C12 N3 C1 C2 -73.2(8) . . . . ?
N2 N3 C1 C2 124.6(6) . . . . ?
N3 C1 C2 C3 40.0(13) . . . . ?
C4 N4 C3 C2 125.5(8) . . . . ?
C11 N4 C3 C2 -65.3(9) . . . . ?
C1 C2 C3 N4 38.5(13) . . . . ?
C12 N3 C1D C2D 17.1(12) . . . . ?
N2 N3 C1D C2D 179.3(7) . . . . ?
N3 C1D C2D C3D -56.5(13) . . . . ?
C1D C2D C3D N4 83.0(10) . . . . ?
C4 N4 C3D C2D 124.1(9) . . . . ?
C11 N4 C3D C2D -44.1(12) . . . . ?
C11 N4 C4 C5 -175.79(17) . . . . ?
C3 N4 C4 C5 -5.4(5) . . . . ?
C3D N4 C4 C5 14.1(6) . . . . ?
C11 N4 C4 C9 1.66(17) . . . . ?
C3 N4 C4 C9 172.1(4) . . . . ?
C3D N4 C4 C9 -168.5(6) . . . . ?
N4 C4 C5 C6 177.24(18) . . . . ?
C9 C4 C5 C6 0.1(3) . . . . ?
C4 C5 C6 C7 0.5(3) . . . . ?
C5 C6 C7 C8 -0.3(4) . . . . ?
C6 C7 C8 C9 -0.5(3) . . . . ?
N4 C4 C9 C8 -178.59(14) . . . . ?
C5 C4 C9 C8 -0.9(2) . . . . ?
N4 C4 C9 C10 -1.08(17) . . . . ?
C5 C4 C9 C10 176.64(15) . . . . ?
C7 C8 C9 C4 1.1(3) . . . . ?
C7 C8 C9 C10 -175.61(18) . . . . ?
C4 C9 C10 C11 0.10(17) . . . . ?
C8 C9 C10 C11 177.07(17) . . . . ?
C9 C10 C11 N4 0.93(17) . . . . ?
C9 C10 C11 C12 -174.23(14) . . . . ?
C4 N4 C11 C10 -1.62(17) . . . . ?
C3 N4 C11 C10 -172.7(4) . . . . ?
C3D N4 C11 C10 168.1(6) . . . . ?
C4 N4 C11 C12 173.98(13) . . . . ?
C3 N4 C11 C12 2.9(5) . . . . ?
C3D N4 C11 C12 -16.3(7) . . . . ?
N2 N3 C12 C13 0.69(19) . . . . ?
C1D N3 C12 C13 162.6(6) . . . . ?
C1 N3 C12 C13 -163.9(3) . . . . ?
N2 N3 C12 C11 179.99(14) . . . . ?
C1D N3 C12 C11 -18.1(7) . . . . ?
C1 N3 C12 C11 15.4(4) . . . . ?
C10 C11 C12 N3 -148.94(17) . . . . ?
N4 C11 C12 N3 36.4(2) . . . . ?
C10 C11 C12 C13 30.1(3) . . . . ?
N4 C11 C12 C13 -144.49(18) . . . . ?
N2 N1 C13 C12 0.01(19) . . . . ?
N2 N1 C13 C14 176.70(16) . . . . ?
N3 C12 C13 N1 -0.42(18) . . . . ?
C11 C12 C13 N1 -179.64(15) . . . . ?
N3 C12 C13 C14 -176.86(16) . . . . ?
C11 C12 C13 C14 3.9(3) . . . . ?
N1 C13 C14 O2 -150.52(18) . . . . ?
C12 C13 C14 O2 25.5(3) . . . . ?
N1 C13 C14 C15 30.3(2) . . . . ?
C12 C13 C14 C15 -153.76(17) . . . . ?
O2 C14 C15 C20 15.5(2) . . . . ?
C13 C14 C15 C20 -165.24(14) . . . . ?
O2 C14 C15 C16 -160.06(17) . . . . ?
C13 C14 C15 C16 19.2(2) . . . . ?
C20 C15 C16 C17 -0.7(3) . . . . ?
C14 C15 C16 C17 174.78(16) . . . . ?
C15 C16 C17 C18 0.9(3) . . . . ?
C16 C17 C18 C19 -0.1(3) . . . . ?
C17 C18 C19 C20 -0.9(3) . . . . ?
C17 C18 C19 N5 -178.07(16) . . . . ?
C21 N5 C19 C20 157.66(17) . . . . ?
C21 N5 C19 C18 -25.1(3) . . . . ?
C18 C19 C20 C15 1.0(2) . . . . ?
N5 C19 C20 C15 178.36(14) . . . . ?
C16 C15 C20 C19 -0.2(2) . . . . ?
C14 C15 C20 C19 -176.01(14) . . . . ?
C19 N5 C21 O1 -1.1(3) . . . . ?
C19 N5 C21 C22 178.96(18) . . . . ?

_refine_diff_density_max         0.376
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.094



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
