# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_ab_21_i_0m
_database_code_depnum_ccdc_archive 'CCDC 2375414'
loop_
_audit_author_name
_audit_author_address
'Aditi Boruah'
;Gauhati University
India
;
_audit_update_record             
;
2024-09-03 deposited with the CCDC.	2024-09-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H15 N5 O'
_chemical_formula_sum            'C22 H15 N5 O'
_chemical_formula_weight         365.39

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                   13.340(6)
_cell_length_b                   7.845(4)
_cell_length_c                   22.448(8)
_cell_angle_alpha                90
_cell_angle_beta                 119.39(2)
_cell_angle_gamma                90
_cell_volume                     2046.9(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5152
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      20.36

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.186
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.077
_shelx_estimated_absorpt_T_min   0.988
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   'Sheldrick,G.M.,2015,University of gottingen'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            58088
_diffrn_reflns_av_unetI/netI     0.2430
_diffrn_reflns_av_R_equivalents  0.2157
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.956
_diffrn_reflns_theta_max         27.666
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.907
_diffrn_measured_fraction_theta_full 0.916
_diffrn_reflns_Laue_measured_fraction_max 0.907
_diffrn_reflns_Laue_measured_fraction_full 0.916
_diffrn_reflns_point_group_measured_fraction_max 0.907
_diffrn_reflns_point_group_measured_fraction_full 0.916
_reflns_number_total             4349
_reflns_number_gt                2063
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.1093P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.061(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4349
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1723
_refine_ls_R_factor_gt           0.1019
_refine_ls_wR_factor_ref         0.2767
_refine_ls_wR_factor_gt          0.2213
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_restrained_S_all      0.957
_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 0.6465(3) 0.4518(4) 0.22645(17) 0.0441(8) Uani 1 1 d . . . . .
C2 C 0.7024(3) 0.6031(5) 0.2331(2) 0.0630(11) Uani 1 1 d . . . . .
H2 H 0.696525 0.656303 0.194506 0.076 Uiso 1 1 calc R U . . .
C3 C 0.7674(4) 0.6774(6) 0.2964(3) 0.0869(16) Uani 1 1 d . . . . .
H3 H 0.803318 0.781679 0.300409 0.104 Uiso 1 1 calc R U . . .
C4 C 0.7786(4) 0.5953(7) 0.3541(3) 0.0831(15) Uani 1 1 d . . . . .
H4 H 0.824532 0.642742 0.397084 0.100 Uiso 1 1 calc R U . . .
C5 C 0.7232(4) 0.4462(7) 0.3482(2) 0.0739(13) Uani 1 1 d . . . . .
H5 H 0.729422 0.394308 0.387120 0.089 Uiso 1 1 calc R U . . .
C6 C 0.6558(3) 0.3684(5) 0.28351(19) 0.0559(9) Uani 1 1 d . . . . .
C7 C 0.5940(4) 0.2059(5) 0.2756(2) 0.0644(11) Uani 1 1 d . . . . .
H7A H 0.518739 0.229202 0.270475 0.077 Uiso 1 1 calc R U . . .
H7B H 0.636513 0.136667 0.316212 0.077 Uiso 1 1 calc R U . . .
C8 C 0.5804(3) 0.1104(4) 0.21441(19) 0.0576(10) Uani 1 1 d . . . . .
H8A H 0.655213 0.074349 0.221756 0.069 Uiso 1 1 calc R U . . .
H8B H 0.533764 0.009545 0.207250 0.069 Uiso 1 1 calc R U . . .
N5 N 0.5246(2) 0.2222(3) 0.15357(13) 0.0422(7) Uani 1 1 d . . . . .
C10 C 0.5723(2) 0.3794(4) 0.15678(16) 0.0399(7) Uani 1 1 d . . . . .
C11 C 0.4506(2) 0.1439(4) 0.09003(16) 0.0395(7) Uani 1 1 d . . . . .
C12 C 0.3537(2) 0.2308(4) 0.03942(17) 0.0402(8) Uani 1 1 d . . . . .
C13 C 0.2872(2) 0.1500(4) -0.02383(16) 0.0397(7) Uani 1 1 d . . . . .
C14 C 0.3220(2) -0.0100(4) -0.03282(16) 0.0420(8) Uani 1 1 d . . . . .
C15 C 0.4151(3) -0.0930(3) 0.02224(17) 0.0408(8) Uani 1 1 d . . . . .
C16 C 0.1840(2) 0.2322(4) -0.08070(18) 0.0436(8) Uani 1 1 d . . . . .
C17 C 0.1913(3) 0.3923(4) -0.10403(19) 0.0552(10) Uani 1 1 d . . . . .
H17 H 0.260625 0.451452 -0.083138 0.066 Uiso 1 1 calc R U . . .
C18 C 0.0950(4) 0.4652(5) -0.1587(2) 0.0750(14) Uani 1 1 d . . . . .
H18 H 0.100411 0.573113 -0.174033 0.090 Uiso 1 1 calc R U . . .
C19 C -0.0077(4) 0.3797(6) -0.1902(2) 0.0788(15) Uani 1 1 d . . . . .
H19 H -0.071828 0.428281 -0.226988 0.095 Uiso 1 1 calc R U . . .
C20 C -0.0143(3) 0.2205(6) -0.1665(3) 0.0776(14) Uani 1 1 d . . . . .
H20 H -0.083875 0.162044 -0.187518 0.093 Uiso 1 1 calc R U . . .
C21 C 0.0787(3) 0.1467(5) -0.1129(2) 0.0609(11) Uani 1 1 d . . . . .
H21 H 0.072022 0.039151 -0.097759 0.073 Uiso 1 1 calc R U . . .
C22 C 0.3180(3) 0.3868(4) 0.05485(18) 0.0493(9) Uani 1 1 d . . . . .
C23 C 0.2694(3) -0.0932(4) -0.09785(19) 0.0501(9) Uani 1 1 d . . . . .
N1 N 0.4801(2) -0.0132(3) 0.08345(14) 0.0425(7) Uani 1 1 d . . . . .
N2 N 0.2852(3) 0.5094(5) 0.06763(19) 0.0747(11) Uani 1 1 d . . . . .
N3 N 0.2344(3) -0.1683(4) -0.14789(18) 0.0659(10) Uani 1 1 d . . . . .
N4 N 0.4490(3) -0.2504(3) 0.01676(17) 0.0538(8) Uani 1 1 d . . . . .
H4A H 0.487622 -0.323397 0.061527 0.065 Uiso 1 1 d R U . . .
H4B H 0.382683 -0.316117 -0.019043 0.065 Uiso 1 1 d R U . . .
O1 O 0.55418(19) 0.4573(3) 0.10468(12) 0.0502(7) 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 C2 1.370(5) . ?
C1 C6 1.389(5) . ?
C1 C10 1.493(4) . ?
C2 C3 1.379(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.355(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.417(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.481(6) . ?
C7 C8 1.495(6) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N5 1.480(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
N5 C10 1.373(4) . ?
N5 C11 1.416(4) . ?
C10 O1 1.234(4) . ?
C11 N1 1.324(4) . ?
C11 C12 1.409(4) . ?
C12 C13 1.403(4) . ?
C12 C22 1.417(5) . ?
C13 C14 1.387(4) . ?
C13 C16 1.489(4) . ?
C14 C15 1.410(4) . ?
C14 C23 1.430(5) . ?
C15 N4 1.341(4) . ?
C15 N1 1.364(4) . ?
C16 C17 1.382(5) . ?
C16 C21 1.397(4) . ?
C17 C18 1.391(5) . ?
C17 H17 0.9300 . ?
C18 C19 1.369(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.378(7) . ?
C19 H19 0.9300 . ?
C20 C21 1.363(6) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 N2 1.150(5) . ?
C23 N3 1.145(5) . ?
N4 H4A 1.0465 . ?
N4 H4B 0.9982 . ?

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 120.7(3) . . ?
C2 C1 C10 119.3(3) . . ?
C6 C1 C10 120.0(3) . . ?
C1 C2 C3 120.8(5) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C2 C3 C4 119.4(4) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 120.4(4) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.9(5) . . ?
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C1 C6 C5 117.8(4) . . ?
C1 C6 C7 120.2(3) . . ?
C5 C6 C7 122.0(4) . . ?
C6 C7 C8 110.5(3) . . ?
C6 C7 H7A 109.5 . . ?
C8 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
N5 C8 C7 109.3(3) . . ?
N5 C8 H8A 109.8 . . ?
C7 C8 H8A 109.8 . . ?
N5 C8 H8B 109.8 . . ?
C7 C8 H8B 109.8 . . ?
H8A C8 H8B 108.3 . . ?
C10 N5 C11 121.2(3) . . ?
C10 N5 C8 118.3(2) . . ?
C11 N5 C8 117.3(2) . . ?
O1 C10 N5 121.7(3) . . ?
O1 C10 C1 121.7(3) . . ?
N5 C10 C1 116.7(3) . . ?
N1 C11 C12 124.4(3) . . ?
N1 C11 N5 114.7(2) . . ?
C12 C11 N5 120.9(3) . . ?
C13 C12 C11 118.2(3) . . ?
C13 C12 C22 121.1(3) . . ?
C11 C12 C22 120.4(3) . . ?
C14 C13 C12 117.7(3) . . ?
C14 C13 C16 120.1(3) . . ?
C12 C13 C16 122.1(3) . . ?
C13 C14 C15 120.3(3) . . ?
C13 C14 C23 122.0(3) . . ?
C15 C14 C23 117.7(3) . . ?
N4 C15 N1 116.0(3) . . ?
N4 C15 C14 122.4(3) . . ?
N1 C15 C14 121.5(3) . . ?
C17 C16 C21 118.7(3) . . ?
C17 C16 C13 120.8(3) . . ?
C21 C16 C13 120.5(3) . . ?
C16 C17 C18 120.1(3) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C19 C18 C17 120.7(4) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 118.8(4) . . ?
C18 C19 H19 120.6 . . ?
C20 C19 H19 120.6 . . ?
C21 C20 C19 121.6(4) . . ?
C21 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C20 C21 C16 120.1(4) . . ?
C20 C21 H21 120.0 . . ?
C16 C21 H21 120.0 . . ?
N2 C22 C12 176.9(4) . . ?
N3 C23 C14 174.7(3) . . ?
C11 N1 C15 117.6(2) . . ?
C15 N4 H4A 116.4 . . ?
C15 N4 H4B 110.1 . . ?
H4A N4 H4B 108.3 . . ?

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 -1.2(6) . . . . ?
C10 C1 C2 C3 177.0(4) . . . . ?
C1 C2 C3 C4 1.8(7) . . . . ?
C2 C3 C4 C5 -2.3(8) . . . . ?
C3 C4 C5 C6 2.1(7) . . . . ?
C2 C1 C6 C5 0.9(5) . . . . ?
C10 C1 C6 C5 -177.3(3) . . . . ?
C2 C1 C6 C7 179.4(3) . . . . ?
C10 C1 C6 C7 1.2(5) . . . . ?
C4 C5 C6 C1 -1.4(6) . . . . ?
C4 C5 C6 C7 -179.8(4) . . . . ?
C1 C6 C7 C8 29.7(5) . . . . ?
C5 C6 C7 C8 -151.9(4) . . . . ?
C6 C7 C8 N5 -54.2(4) . . . . ?
C7 C8 N5 C10 53.2(4) . . . . ?
C7 C8 N5 C11 -146.7(3) . . . . ?
C11 N5 C10 O1 -1.2(5) . . . . ?
C8 N5 C10 O1 158.1(3) . . . . ?
C11 N5 C10 C1 178.4(3) . . . . ?
C8 N5 C10 C1 -22.4(4) . . . . ?
C2 C1 C10 O1 -4.6(5) . . . . ?
C6 C1 C10 O1 173.6(3) . . . . ?
C2 C1 C10 N5 175.8(3) . . . . ?
C6 C1 C10 N5 -5.9(4) . . . . ?
C10 N5 C11 N1 127.2(3) . . . . ?
C8 N5 C11 N1 -32.3(4) . . . . ?
C10 N5 C11 C12 -53.2(4) . . . . ?
C8 N5 C11 C12 147.4(3) . . . . ?
N1 C11 C12 C13 -3.8(5) . . . . ?
N5 C11 C12 C13 176.6(3) . . . . ?
N1 C11 C12 C22 169.5(3) . . . . ?
N5 C11 C12 C22 -10.1(5) . . . . ?
C11 C12 C13 C14 -0.7(5) . . . . ?
C22 C12 C13 C14 -174.0(3) . . . . ?
C11 C12 C13 C16 -179.4(3) . . . . ?
C22 C12 C13 C16 7.4(5) . . . . ?
C12 C13 C14 C15 5.5(5) . . . . ?
C16 C13 C14 C15 -175.9(3) . . . . ?
C12 C13 C14 C23 -171.7(3) . . . . ?
C16 C13 C14 C23 7.0(5) . . . . ?
C13 C14 C15 N4 177.3(3) . . . . ?
C23 C14 C15 N4 -5.4(5) . . . . ?
C13 C14 C15 N1 -6.3(5) . . . . ?
C23 C14 C15 N1 171.0(3) . . . . ?
C14 C13 C16 C17 -124.4(4) . . . . ?
C12 C13 C16 C17 54.2(5) . . . . ?
C14 C13 C16 C21 53.7(5) . . . . ?
C12 C13 C16 C21 -127.8(4) . . . . ?
C21 C16 C17 C18 -0.2(6) . . . . ?
C13 C16 C17 C18 177.9(4) . . . . ?
C16 C17 C18 C19 -0.2(8) . . . . ?
C17 C18 C19 C20 0.5(8) . . . . ?
C18 C19 C20 C21 -0.3(8) . . . . ?
C19 C20 C21 C16 -0.1(8) . . . . ?
C17 C16 C21 C20 0.4(6) . . . . ?
C13 C16 C21 C20 -177.7(4) . . . . ?
C12 C11 N1 C15 3.2(5) . . . . ?
N5 C11 N1 C15 -177.2(3) . . . . ?
N4 C15 N1 C11 178.5(3) . . . . ?
C14 C15 N1 C11 1.8(5) . . . . ?

_refine_diff_density_max         1.135
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.096

####################################################################### 
# 
# 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_pn_01_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2375415'
loop_
_audit_author_name
_audit_author_address
'Aditi Boruah'
;Gauhati University
India
;
_audit_update_record             
;
2024-09-03 deposited with the CCDC.	2024-09-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H17 N5'
_chemical_formula_sum            'C22 H17 N5'
_chemical_formula_weight         351.40

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'

_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                   16.101(5)
_cell_length_b                   7.088(3)
_cell_length_c                   17.585(6)
_cell_angle_alpha                90
_cell_angle_beta                 112.166(7)
_cell_angle_gamma                90
_cell_volume                     1858.6(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    1490
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      22.17

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.078
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.984
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   'Bruker AXS SADABS program'
_exptl_absorpt_special_details   Sheldrick,G.M.,(2003)
_diffrn_ambient_temperature      273(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5939
_diffrn_reflns_av_unetI/netI     0.1086
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.272
_diffrn_reflns_theta_max         30.484
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.644
_diffrn_measured_fraction_theta_full 0.747
_diffrn_reflns_Laue_measured_fraction_max 0.644
_diffrn_reflns_Laue_measured_fraction_full 0.747
_diffrn_reflns_point_group_measured_fraction_max 0.644
_diffrn_reflns_point_group_measured_fraction_full 0.747
_reflns_number_total             3641
_reflns_number_gt                1936
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_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)+(0.0106P)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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3641
_refine_ls_number_parameters     252
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1018
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1225
_refine_ls_wR_factor_gt          0.1067
_refine_ls_goodness_of_fit_ref   0.896
_refine_ls_restrained_S_all      0.896
_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 0.44947(10) 0.1910(2) 0.72228(9) 0.0395(5) Uani 1 1 d . . . . .
H1A H 0.467544 0.293798 0.761572 0.047 Uiso 1 1 calc R U . . .
H1B H 0.453946 0.074818 0.752691 0.047 Uiso 1 1 calc R U . . .
C2 C 0.35242(12) 0.2205(2) 0.66520(10) 0.0424(5) Uani 1 1 d . . . . .
C3 C 0.28857(14) 0.2431(2) 0.69954(13) 0.0556(6) Uani 1 1 d . . . . .
H3 H 0.305918 0.237050 0.756275 0.067 Uiso 1 1 calc R U . . .
C4 C 0.19921(13) 0.2745(3) 0.65090(16) 0.0725(7) Uani 1 1 d . . . . .
H4 H 0.157120 0.290965 0.674822 0.087 Uiso 1 1 calc R U . . .
C5 C 0.17322(15) 0.2811(3) 0.56631(17) 0.0792(8) Uani 1 1 d . . . . .
H5 H 0.113359 0.300373 0.532971 0.095 Uiso 1 1 calc R U . . .
C6 C 0.23612(15) 0.2590(3) 0.53215(13) 0.0691(7) Uani 1 1 d . . . . .
H6 H 0.218269 0.265639 0.475381 0.083 Uiso 1 1 calc R U . . .
C7 C 0.32709(12) 0.2264(2) 0.58043(11) 0.0516(6) Uani 1 1 d . . . . .
C8 C 0.39488(12) 0.1933(3) 0.54202(9) 0.0568(6) Uani 1 1 d . . . . .
H8A H 0.415964 0.313346 0.529799 0.068 Uiso 1 1 calc R U . . .
H8B H 0.367170 0.124629 0.490919 0.068 Uiso 1 1 calc R U . . .
C9 C 0.47361(9) 0.0809(2) 0.60031(7) 0.0438(5) Uani 1 1 d . . . . .
H9A H 0.453825 -0.044047 0.608515 0.053 Uiso 1 1 calc R U . . .
H9B H 0.519323 0.067221 0.577242 0.053 Uiso 1 1 calc R U . . .
C10 C 0.60082(11) 0.2060(2) 0.72249(8) 0.0324(5) Uani 1 1 d . . . . .
C11 C 0.66334(11) 0.2320(2) 0.68459(8) 0.0351(5) Uani 1 1 d . . . . .
C12 C 0.75576(11) 0.2487(2) 0.73358(8) 0.0360(5) Uani 1 1 d . . . . .
C13 C 0.78040(11) 0.2477(2) 0.81846(8) 0.0353(5) Uani 1 1 d . . . . .
C14 C 0.71347(12) 0.2342(2) 0.85142(8) 0.0345(5) Uani 1 1 d . . . . .
C15 C 0.63645(11) 0.2746(2) 0.59863(9) 0.0439(5) Uani 1 1 d . . . . .
C16 C 0.82345(12) 0.2689(3) 0.69602(9) 0.0436(5) Uani 1 1 d . . . . .
C17 C 0.84047(14) 0.1227(3) 0.65253(11) 0.0666(6) Uani 1 1 d . . . . .
H17 H 0.809240 0.009896 0.647104 0.080 Uiso 1 1 calc R U . . .
C18 C 0.90314(18) 0.1404(5) 0.61677(12) 0.0869(8) Uani 1 1 d . . . . .
H18 H 0.914991 0.039397 0.588668 0.104 Uiso 1 1 calc R U . . .
C19 C 0.94784(15) 0.3084(6) 0.62300(13) 0.0984(10) Uani 1 1 d . . . . .
H19 H 0.988488 0.322724 0.597345 0.118 Uiso 1 1 calc R U . . .
C20 C 0.93260(16) 0.4551(5) 0.66701(16) 0.1016(9) Uani 1 1 d . . . . .
H20 H 0.963730 0.567958 0.672105 0.122 Uiso 1 1 calc R U . . .
C21 C 0.87093(15) 0.4347(3) 0.70368(12) 0.0785(7) Uani 1 1 d . . . . .
H21 H 0.861242 0.533951 0.733944 0.094 Uiso 1 1 calc R U . . .
C22 C 0.87323(11) 0.2586(2) 0.87238(9) 0.0479(5) Uani 1 1 d . . . . .
H3A H 0.7981(4) 0.257(2) 0.9696(10) 0.086(7) Uiso 1 1 d D . . . .
H3B H 0.6876(9) 0.221(3) 0.9591(10) 0.096(8) Uiso 1 1 d D . . . .
N1 N 0.51064(8) 0.18177(18) 0.67930(6) 0.0384(4) Uani 1 1 d . . . . .
N2 N 0.62546(8) 0.21203(16) 0.80441(6) 0.0355(4) Uani 1 1 d . . . . .
N3 N 0.73304(10) 0.2397(2) 0.93288(7) 0.0482(4) Uani 1 1 d D . . . .
N4 N 0.61493(10) 0.3120(2) 0.53104(7) 0.0632(5) Uani 1 1 d . . . . .
N5 N 0.94582(10) 0.2659(2) 0.91852(9) 0.0738(6) 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 N1 1.452(2) . ?
C1 C2 1.520(2) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.384(3) . ?
C2 C7 1.390(3) . ?
C3 C4 1.387(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.386(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.367(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.407(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.503(3) . ?
C8 C9 1.521(2) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N1 1.4737(16) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 N2 1.3429(18) . ?
C10 N1 1.3719(19) . ?
C10 C11 1.413(3) . ?
C11 C12 1.415(2) . ?
C11 C15 1.439(2) . ?
C12 C13 1.392(2) . ?
C12 C16 1.479(3) . ?
C13 C14 1.406(2) . ?
C13 C22 1.439(2) . ?
C14 N3 1.346(2) . ?
C14 N2 1.354(2) . ?
C15 N4 1.1368(19) . ?
C16 C17 1.375(3) . ?
C16 C21 1.381(3) . ?
C17 C18 1.381(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.374(4) . ?
C18 H18 0.9300 . ?
C19 C20 1.372(4) . ?
C19 H19 0.9300 . ?
C20 C21 1.381(3) . ?
C20 H20 0.9300 . ?
C21 H21 0.9300 . ?
C22 N5 1.1452(19) . ?
N3 H3A 1.0096(11) . ?
N3 H3B 1.0099(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
N1 C1 C2 113.14(14) . . ?
N1 C1 H1A 109.0 . . ?
C2 C1 H1A 109.0 . . ?
N1 C1 H1B 109.0 . . ?
C2 C1 H1B 109.0 . . ?
H1A C1 H1B 107.8 . . ?
C3 C2 C7 119.92(17) . . ?
C3 C2 C1 118.40(16) . . ?
C7 C2 C1 121.68(19) . . ?
C2 C3 C4 121.2(2) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C6 C5 C4 119.60(19) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
C5 C6 C7 121.9(2) . . ?
C5 C6 H6 119.0 . . ?
C7 C6 H6 119.0 . . ?
C2 C7 C6 118.0(2) . . ?
C2 C7 C8 120.54(15) . . ?
C6 C7 C8 121.44(18) . . ?
C7 C8 C9 109.95(14) . . ?
C7 C8 H8A 109.7 . . ?
C9 C8 H8A 109.7 . . ?
C7 C8 H8B 109.7 . . ?
C9 C8 H8B 109.7 . . ?
H8A C8 H8B 108.2 . . ?
N1 C9 C8 108.60(14) . . ?
N1 C9 H9A 110.0 . . ?
C8 C9 H9A 110.0 . . ?
N1 C9 H9B 110.0 . . ?
C8 C9 H9B 110.0 . . ?
H9A C9 H9B 108.4 . . ?
N2 C10 N1 114.86(16) . . ?
N2 C10 C11 121.80(13) . . ?
N1 C10 C11 123.28(12) . . ?
C10 C11 C12 119.75(13) . . ?
C10 C11 C15 122.50(14) . . ?
C12 C11 C15 116.90(17) . . ?
C13 C12 C11 117.45(18) . . ?
C13 C12 C16 121.29(14) . . ?
C11 C12 C16 121.26(13) . . ?
C12 C13 C14 119.31(14) . . ?
C12 C13 C22 120.75(18) . . ?
C14 C13 C22 119.94(13) . . ?
N3 C14 N2 115.09(19) . . ?
N3 C14 C13 121.91(14) . . ?
N2 C14 C13 123.00(13) . . ?
N4 C15 C11 178.59(18) . . ?
C17 C16 C21 118.5(2) . . ?
C17 C16 C12 120.71(18) . . ?
C21 C16 C12 120.83(18) . . ?
C16 C17 C18 121.2(2) . . ?
C16 C17 H17 119.4 . . ?
C18 C17 H17 119.4 . . ?
C19 C18 C17 119.6(2) . . ?
C19 C18 H18 120.2 . . ?
C17 C18 H18 120.2 . . ?
C20 C19 C18 120.1(2) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 119.8(3) . . ?
C19 C20 H20 120.1 . . ?
C21 C20 H20 120.1 . . ?
C20 C21 C16 120.9(2) . . ?
C20 C21 H21 119.6 . . ?
C16 C21 H21 119.6 . . ?
N5 C22 C13 176.60(19) . . ?
C10 N1 C1 119.37(11) . . ?
C10 N1 C9 123.35(13) . . ?
C1 N1 C9 113.58(12) . . ?
C10 N2 C14 118.45(16) . . ?
C14 N3 H3A 117.0(12) . . ?
C14 N3 H3B 124.2(11) . . ?
H3A N3 H3B 118.7(17) . . ?

_refine_diff_density_max         0.176
_refine_diff_density_min         -0.183
_refine_diff_density_rms         0.032

