# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_7a_amis22
_database_code_depnum_ccdc_archive 'CCDC 1980577'
loop_
_audit_author_name
_audit_author_address
'Matti Haukka'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-01-29 deposited with the CCDC.	2020-08-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H18 N4 O2, C2 H6 O'
_chemical_formula_sum            'C21 H24 N4 O3'
_chemical_formula_weight         380.44

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                   9.5893(2)
_cell_length_b                   14.2652(5)
_cell_length_c                   15.8257(5)
_cell_angle_alpha                104.318(3)
_cell_angle_beta                 104.565(3)
_cell_angle_gamma                103.319(3)
_cell_volume                     1928.87(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    8785
_cell_measurement_theta_min      2.2700
_cell_measurement_theta_max      30.0460

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.308
_exptl_crystal_size_mid          0.183
_exptl_crystal_size_min          0.105
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_T_min  0.88049
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'φ scans and ω scans with κ offset'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_detector_area_resol_mean 16.0107
_diffrn_reflns_number            34591
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.277
_diffrn_reflns_theta_max         30.628
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.906
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.906
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.906
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             10787
_reflns_number_gt                8088
_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 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
;
_computing_cell_refinement       
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
;
_computing_data_reduction        
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    
'CrystaMaker X (CrystalMaker Software ltd., 2019)'
_computing_publication_material  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0618P)²+0.6436P] 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         10787
_refine_ls_number_parameters     519
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0714
_refine_ls_R_factor_gt           0.0492
_refine_ls_wR_factor_ref         0.1363
_refine_ls_wR_factor_gt          0.1219
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
O1 O 0.47027(14) 0.63728(9) 0.72194(8) 0.0384(3) Uani 1 1 d . . . . .
O2 O 0.23784(12) 0.15221(8) 0.69199(7) 0.0293(2) Uani 1 1 d . . . . .
N1 N 0.57494(13) 0.45432(8) 0.90628(7) 0.0223(2) Uani 1 1 d . . . . .
N2 N 0.62722(13) 0.55170(9) 0.90396(8) 0.0246(2) Uani 1 1 d . . . . .
N3 N 0.43754(13) 0.45538(9) 0.77544(8) 0.0234(2) Uani 1 1 d . . . . .
N4 N 0.39738(13) 0.29451(9) 0.80559(8) 0.0244(2) Uani 1 1 d . . . . .
C1 C 0.90922(18) 0.31955(12) 1.17970(11) 0.0339(3) Uani 1 1 d . . . . .
H1A H 0.907418 0.250683 1.148103 0.051 Uiso 1 1 calc R U . . .
H1B H 0.863889 0.317856 1.228539 0.051 Uiso 1 1 calc R U . . .
H1C H 1.014327 0.364564 1.206890 0.051 Uiso 1 1 calc R U . . .
C2 C 0.82005(16) 0.35886(11) 1.11135(9) 0.0253(3) Uani 1 1 d . . . . .
C3 C 0.89017(16) 0.44243(11) 1.08971(9) 0.0270(3) Uani 1 1 d . . . . .
H3 H 0.995105 0.477528 1.120861 0.032 Uiso 1 1 calc R U . . .
C4 C 0.80907(16) 0.47529(10) 1.02326(9) 0.0256(3) Uani 1 1 d . . . . .
H4 H 0.858375 0.531821 1.008435 0.031 Uiso 1 1 calc R U . . .
C5 C 0.65559(15) 0.42480(10) 0.97882(9) 0.0215(3) Uani 1 1 d . . . . .
C6 C 0.58119(16) 0.34347(11) 1.00127(9) 0.0245(3) Uani 1 1 d . . . . .
H6 H 0.475172 0.310780 0.972315 0.029 Uiso 1 1 calc R U . . .
C7 C 0.66507(16) 0.31085(11) 1.06702(9) 0.0261(3) Uani 1 1 d . . . . .
H7 H 0.615455 0.254543 1.081994 0.031 Uiso 1 1 calc R U . . .
C8 C 0.54184(16) 0.54979(10) 0.82435(9) 0.0245(3) Uani 1 1 d . . . . .
C9 C 0.55835(17) 0.64110(11) 0.79362(10) 0.0287(3) Uani 1 1 d . . . . .
C10 C 0.68648(18) 0.73408(11) 0.85574(11) 0.0337(3) Uani 1 1 d . . . . .
H10A H 0.782063 0.725971 0.848639 0.051 Uiso 1 1 calc R U . . .
H10B H 0.690749 0.743603 0.919934 0.051 Uiso 1 1 calc R U . . .
H10C H 0.670661 0.793648 0.839400 0.051 Uiso 1 1 calc R U . . .
C11 C 0.46188(15) 0.39291(10) 0.82634(9) 0.0220(3) Uani 1 1 d . . . . .
C12 C 0.32914(15) 0.41821(11) 0.68140(9) 0.0238(3) Uani 1 1 d . . . . .
H12 H 0.380456 0.439830 0.638502 0.029 Uiso 1 1 calc R U . . .
C13 C 0.18679(17) 0.45515(12) 0.67538(10) 0.0298(3) Uani 1 1 d . . . . .
H13 H 0.205444 0.526824 0.713730 0.036 Uiso 1 1 calc R U . . .
C14 C 0.10908(17) 0.42761(13) 0.57251(10) 0.0337(3) Uani 1 1 d . . . . .
H14 H 0.102442 0.473838 0.538672 0.040 Uiso 1 1 calc R U . . .
C15 C 0.05200(18) 0.32676(14) 0.53852(11) 0.0384(4) Uani 1 1 d . . . . .
H15 H -0.001016 0.287771 0.475513 0.046 Uiso 1 1 calc R U . . .
C16 C 0.08631(16) 0.28471(13) 0.61795(11) 0.0334(3) Uani 1 1 d . . . . .
H16 H 0.019011 0.215159 0.607724 0.040 Uiso 1 1 calc R U . . .
C17 C 0.08294(18) 0.37132(14) 0.69661(11) 0.0363(4) Uani 1 1 d . . . . .
H17A H -0.019788 0.377696 0.688953 0.044 Uiso 1 1 calc R U . . .
H17B H 0.127596 0.366433 0.758355 0.044 Uiso 1 1 calc R U . . .
C18 C 0.26112(15) 0.30004(11) 0.64784(9) 0.0248(3) Uani 1 1 d . . . . .
H18 H 0.288585 0.270408 0.592473 0.030 Uiso 1 1 calc R U . . .
C19 C 0.29944(15) 0.24511(11) 0.71783(9) 0.0243(3) Uani 1 1 d . . . . .
O3 O 0.53586(13) -0.08631(8) 0.79394(8) 0.0373(3) Uani 1 1 d . . . . .
O4 O 0.75983(11) 0.38025(7) 0.77732(7) 0.0290(2) Uani 1 1 d . . . . .
N5 N 0.42466(12) 0.06651(8) 0.58381(8) 0.0222(2) Uani 1 1 d . . . . .
N6 N 0.37353(13) -0.02555(9) 0.59629(8) 0.0247(2) Uani 1 1 d . . . . .
N7 N 0.56832(12) 0.07981(8) 0.71836(8) 0.0222(2) Uani 1 1 d . . . . .
N8 N 0.60346(13) 0.23068(9) 0.67154(8) 0.0232(2) Uani 1 1 d . . . . .
C20 C 0.07733(18) 0.16327(13) 0.28576(11) 0.0359(3) Uani 1 1 d . . . . .
H20A H -0.028781 0.120770 0.265177 0.054 Uiso 1 1 calc R U . . .
H20B H 0.117135 0.151461 0.234124 0.054 Uiso 1 1 calc R U . . .
H20C H 0.083763 0.235176 0.307732 0.054 Uiso 1 1 calc R U . . .
C21 C 0.16921(16) 0.13628(11) 0.36290(9) 0.0266(3) Uani 1 1 d . . . . .
C22 C 0.10022(16) 0.06377(11) 0.39741(10) 0.0272(3) Uani 1 1 d . . . . .
H22 H -0.005959 0.030320 0.371034 0.033 Uiso 1 1 calc R U . . .
C23 C 0.18404(16) 0.03977(11) 0.46952(9) 0.0254(3) Uani 1 1 d . . . . .
H23 H 0.135715 -0.008903 0.493074 0.030 Uiso 1 1 calc R U . . .
C24 C 0.33960(15) 0.08787(10) 0.50682(9) 0.0217(3) Uani 1 1 d . . . . .
C25 C 0.41183(15) 0.15837(10) 0.47240(9) 0.0245(3) Uani 1 1 d . . . . .
H25 H 0.518608 0.189710 0.497222 0.029 Uiso 1 1 calc R U . . .
C26 C 0.32539(16) 0.18231(11) 0.40107(9) 0.0266(3) Uani 1 1 d . . . . .
H26 H 0.373996 0.231205 0.377825 0.032 Uiso 1 1 calc R U . . .
C27 C 0.46217(15) -0.01531(10) 0.67783(9) 0.0235(3) Uani 1 1 d . . . . .
C28 C 0.44518(16) -0.09740(11) 0.72033(10) 0.0285(3) Uani 1 1 d . . . . .
C29 C 0.31145(17) -0.19062(11) 0.66746(11) 0.0331(3) Uani 1 1 d . . . . .
H29A H 0.326391 -0.246890 0.689959 0.050 Uiso 1 1 calc R U . . .
H29B H 0.300856 -0.209092 0.601741 0.050 Uiso 1 1 calc R U . . .
H29C H 0.219498 -0.176947 0.676041 0.050 Uiso 1 1 calc R U . . .
C30 C 0.54070(14) 0.13388(10) 0.65970(9) 0.0215(3) Uani 1 1 d . . . . .
C31 C 0.68629(15) 0.12390(10) 0.80938(9) 0.0225(3) Uani 1 1 d . . . . .
H31 H 0.642784 0.110913 0.858106 0.027 Uiso 1 1 calc R U . . .
C32 C 0.82399(16) 0.08253(11) 0.81242(10) 0.0271(3) Uani 1 1 d . . . . .
H32 H 0.799273 0.007914 0.780843 0.032 Uiso 1 1 calc R U . . .
C33 C 0.91995(16) 0.12303(12) 0.91367(10) 0.0315(3) Uani 1 1 d . . . . .
H33 H 0.933412 0.084127 0.954153 0.038 Uiso 1 1 calc R U . . .
C34 C 0.98169(17) 0.22293(12) 0.93529(10) 0.0320(3) Uani 1 1 d . . . . .
H34 H 1.046539 0.268472 0.994293 0.038 Uiso 1 1 calc R U . . .
C35 C 0.93023(15) 0.25114(11) 0.84912(9) 0.0270(3) Uani 1 1 d . . . . .
H35 H 0.995162 0.316498 0.848274 0.032 Uiso 1 1 calc R U . . .
C36 C 0.91796(16) 0.15424(12) 0.77478(10) 0.0295(3) Uani 1 1 d . . . . .
H36A H 0.862435 0.150766 0.711645 0.035 Uiso 1 1 calc R U . . .
H36B H 1.017529 0.144126 0.777536 0.035 Uiso 1 1 calc R U . . .
C37 C 0.75767(15) 0.24036(10) 0.83093(9) 0.0225(3) Uani 1 1 d . . . . .
H37 H 0.744281 0.277783 0.889221 0.027 Uiso 1 1 calc R U . . .
C38 C 0.70472(15) 0.28700(10) 0.75687(9) 0.0227(3) Uani 1 1 d . . . . .
O5 O 0.27375(15) 0.02773(9) 0.79801(8) 0.0390(3) Uani 1 1 d . . . . .
C39 C 0.3175(2) 0.07442(13) 0.89453(11) 0.0388(4) Uani 1 1 d . . . . .
H39A H 0.258466 0.121281 0.908403 0.047 Uiso 1 1 calc R U . . .
H39B H 0.426360 0.114734 0.918840 0.047 Uiso 1 1 calc R U . . .
C40 C 0.2906(3) -0.00397(18) 0.93973(14) 0.0763(8) Uani 1 1 d . . . . .
H40A H 0.181525 -0.038952 0.920456 0.115 Uiso 1 1 calc R U . . .
H40B H 0.329954 0.028485 1.006874 0.115 Uiso 1 1 calc R U . . .
H40C H 0.342594 -0.053429 0.921827 0.115 Uiso 1 1 calc R U . . .
O6 O 0.71606(14) 0.52749(9) 0.69943(8) 0.0370(3) Uani 1 1 d . . . . .
C41 C 0.7378(2) 0.51893(13) 0.61289(11) 0.0414(4) Uani 1 1 d . . . . .
H41A H 0.845513 0.525288 0.620120 0.050 Uiso 1 1 calc R U . . .
H41B H 0.715517 0.575839 0.592745 0.050 Uiso 1 1 calc R U . . .
C42 C 0.6404(3) 0.42087(15) 0.54018(13) 0.0542(5) Uani 1 1 d . . . . .
H42A H 0.657185 0.420213 0.481480 0.081 Uiso 1 1 calc R U . . .
H42B H 0.533652 0.413512 0.533325 0.081 Uiso 1 1 calc R U . . .
H42C H 0.666361 0.364299 0.557866 0.081 Uiso 1 1 calc R U . . .
H6A H 0.724(2) 0.4723(16) 0.7131(14) 0.051(6) Uiso 1 1 d . . . . .
H5 H 0.272(2) 0.0768(18) 0.7719(15) 0.060(6) 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 C9 1.2123(17) . yes
O2 C19 1.2339(17) . yes
N1 C11 1.3667(17) . yes
N1 N2 1.3769(16) . yes
N1 C5 1.4269(16) . yes
N2 C8 1.3086(17) . yes
N3 C11 1.3615(16) . yes
N3 C8 1.3740(18) . yes
N3 C12 1.4677(16) . yes
N4 C11 1.3155(18) . yes
N4 C19 1.3648(17) . yes
C1 C2 1.5069(18) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C7 1.392(2) . ?
C2 C3 1.393(2) . ?
C3 C4 1.3896(18) . ?
C3 H3 0.9500 . ?
C4 C5 1.3857(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.3897(19) . ?
C6 C7 1.3918(18) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.4883(19) . ?
C9 C10 1.494(2) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C12 C18 1.557(2) . ?
C12 C13 1.5623(18) . ?
C12 H12 1.0000 . ?
C13 C14 1.516(2) . ?
C13 C17 1.534(2) . ?
C13 H13 1.0000 . ?
C14 C15 1.329(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.518(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.535(2) . ?
C16 C18 1.5693(19) . ?
C16 H16 1.0000 . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.5275(19) . ?
C18 H18 1.0000 . ?
O3 C28 1.2142(17) . yes
O4 C38 1.2372(17) . yes
N5 C30 1.3668(17) . yes
N5 N6 1.3727(15) . yes
N5 C24 1.4287(16) . yes
N6 C27 1.3064(17) . yes
N7 C30 1.3607(16) . yes
N7 C27 1.3760(17) . yes
N7 C31 1.4679(16) . yes
N8 C30 1.3179(17) . yes
N8 C38 1.3625(17) . yes
C20 C21 1.5043(19) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 C26 1.391(2) . ?
C21 C22 1.397(2) . ?
C22 C23 1.3872(19) . ?
C22 H22 0.9500 . ?
C23 C24 1.3891(18) . ?
C23 H23 0.9500 . ?
C24 C25 1.3885(19) . ?
C25 C26 1.3886(18) . ?
C25 H25 0.9500 . ?
C26 H26 0.9500 . ?
C27 C28 1.4855(19) . ?
C28 C29 1.496(2) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C31 C37 1.5566(19) . ?
C31 C32 1.5605(18) . ?
C31 H31 1.0000 . ?
C32 C33 1.518(2) . ?
C32 C36 1.536(2) . ?
C32 H32 1.0000 . ?
C33 C34 1.329(2) . ?
C33 H33 0.9500 . ?
C34 C35 1.513(2) . ?
C34 H34 0.9500 . ?
C35 C36 1.536(2) . ?
C35 C37 1.5703(18) . ?
C35 H35 1.0000 . ?
C36 H36A 0.9900 . ?
C36 H36B 0.9900 . ?
C37 C38 1.5220(18) . ?
C37 H37 1.0000 . ?
O5 C39 1.4138(19) . yes
O5 H5 0.90(2) . ?
C39 C40 1.478(3) . ?
C39 H39A 0.9900 . ?
C39 H39B 0.9900 . ?
C40 H40A 0.9800 . ?
C40 H40B 0.9800 . ?
C40 H40C 0.9800 . ?
O6 C41 1.4167(19) . ?
O6 H6A 0.88(2) . ?
C41 C42 1.488(2) . yes
C41 H41A 0.9900 . ?
C41 H41B 0.9900 . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C11 N1 N2 111.50(10) . . ?
C11 N1 C5 127.79(11) . . ?
N2 N1 C5 119.73(11) . . ?
C8 N2 N1 104.37(11) . . ?
C11 N3 C8 107.29(11) . . ?
C11 N3 C12 122.66(11) . . ?
C8 N3 C12 129.67(11) . . ?
C11 N4 C19 116.07(11) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C7 C2 C3 118.38(12) . . ?
C7 C2 C1 120.40(13) . . ?
C3 C2 C1 121.21(13) . . ?
C4 C3 C2 121.04(13) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C4 C3 119.35(13) . . ?
C5 C4 H4 120.3 . . ?
C3 C4 H4 120.3 . . ?
C4 C5 C6 120.97(12) . . ?
C4 C5 N1 119.17(12) . . ?
C6 C5 N1 119.80(12) . . ?
C5 C6 C7 118.68(13) . . ?
C5 C6 H6 120.7 . . ?
C7 C6 H6 120.7 . . ?
C6 C7 C2 121.51(13) . . ?
C6 C7 H7 119.2 . . ?
C2 C7 H7 119.2 . . ?
N2 C8 N3 111.85(12) . . ?
N2 C8 C9 122.52(13) . . ?
N3 C8 C9 125.63(12) . . ?
O1 C9 C8 120.04(14) . . ?
O1 C9 C10 123.78(13) . . ?
C8 C9 C10 116.18(12) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N4 C11 N3 129.62(12) . . ?
N4 C11 N1 125.49(12) . . ?
N3 C11 N1 104.87(11) . . ?
N3 C12 C18 110.65(10) . . ?
N3 C12 C13 112.75(11) . . ?
C18 C12 C13 103.47(11) . . ?
N3 C12 H12 109.9 . . ?
C18 C12 H12 109.9 . . ?
C13 C12 H12 109.9 . . ?
C14 C13 C17 100.51(13) . . ?
C14 C13 C12 103.64(11) . . ?
C17 C13 C12 101.10(11) . . ?
C14 C13 H13 116.4 . . ?
C17 C13 H13 116.4 . . ?
C12 C13 H13 116.4 . . ?
C15 C14 C13 107.21(13) . . ?
C15 C14 H14 126.4 . . ?
C13 C14 H14 126.4 . . ?
C14 C15 C16 108.06(14) . . ?
C14 C15 H15 126.0 . . ?
C16 C15 H15 126.0 . . ?
C15 C16 C17 100.46(13) . . ?
C15 C16 C18 106.16(12) . . ?
C17 C16 C18 99.64(12) . . ?
C15 C16 H16 116.1 . . ?
C17 C16 H16 116.1 . . ?
C18 C16 H16 116.1 . . ?
C13 C17 C16 94.21(12) . . ?
C13 C17 H17A 112.9 . . ?
C16 C17 H17A 112.9 . . ?
C13 C17 H17B 112.9 . . ?
C16 C17 H17B 112.9 . . ?
H17A C17 H17B 110.3 . . ?
C19 C18 C12 117.74(11) . . ?
C19 C18 C16 108.84(11) . . ?
C12 C18 C16 101.85(11) . . ?
C19 C18 H18 109.3 . . ?
C12 C18 H18 109.3 . . ?
C16 C18 H18 109.3 . . ?
O2 C19 N4 120.11(12) . . ?
O2 C19 C18 117.15(12) . . ?
N4 C19 C18 122.74(12) . . ?
C30 N5 N6 111.56(10) . . ?
C30 N5 C24 127.51(11) . . ?
N6 N5 C24 119.76(11) . . ?
C27 N6 N5 104.49(11) . . ?
C30 N7 C27 107.18(11) . . ?
C30 N7 C31 122.89(11) . . ?
C27 N7 C31 129.82(11) . . ?
C30 N8 C38 115.68(11) . . ?
C21 C20 H20A 109.5 . . ?
C21 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C21 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C26 C21 C22 118.34(12) . . ?
C26 C21 C20 120.74(13) . . ?
C22 C21 C20 120.91(13) . . ?
C23 C22 C21 121.15(13) . . ?
C23 C22 H22 119.4 . . ?
C21 C22 H22 119.4 . . ?
C22 C23 C24 119.11(13) . . ?
C22 C23 H23 120.4 . . ?
C24 C23 H23 120.4 . . ?
C25 C24 C23 121.01(12) . . ?
C25 C24 N5 119.95(12) . . ?
C23 C24 N5 119.01(12) . . ?
C24 C25 C26 118.89(13) . . ?
C24 C25 H25 120.6 . . ?
C26 C25 H25 120.6 . . ?
C25 C26 C21 121.46(13) . . ?
C25 C26 H26 119.3 . . ?
C21 C26 H26 119.3 . . ?
N6 C27 N7 111.80(11) . . ?
N6 C27 C28 122.81(13) . . ?
N7 C27 C28 125.38(12) . . ?
O3 C28 C27 120.26(13) . . ?
O3 C28 C29 123.88(13) . . ?
C27 C28 C29 115.86(12) . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N8 C30 N7 129.61(12) . . ?
N8 C30 N5 125.49(12) . . ?
N7 C30 N5 104.83(11) . . ?
N7 C31 C37 110.19(10) . . ?
N7 C31 C32 112.19(11) . . ?
C37 C31 C32 103.43(11) . . ?
N7 C31 H31 110.3 . . ?
C37 C31 H31 110.3 . . ?
C32 C31 H31 110.3 . . ?
C33 C32 C36 100.29(12) . . ?
C33 C32 C31 104.29(11) . . ?
C36 C32 C31 100.98(11) . . ?
C33 C32 H32 116.3 . . ?
C36 C32 H32 116.3 . . ?
C31 C32 H32 116.3 . . ?
C34 C33 C32 107.43(13) . . ?
C34 C33 H33 126.3 . . ?
C32 C33 H33 126.3 . . ?
C33 C34 C35 107.77(13) . . ?
C33 C34 H34 126.1 . . ?
C35 C34 H34 126.1 . . ?
C34 C35 C36 100.52(12) . . ?
C34 C35 C37 106.04(11) . . ?
C36 C35 C37 100.18(11) . . ?
C34 C35 H35 115.9 . . ?
C36 C35 H35 116.0 . . ?
C37 C35 H35 116.0 . . ?
C32 C36 C35 93.93(11) . . ?
C32 C36 H36A 112.9 . . ?
C35 C36 H36A 112.9 . . ?
C32 C36 H36B 112.9 . . ?
C35 C36 H36B 112.9 . . ?
H36A C36 H36B 110.4 . . ?
C38 C37 C31 118.16(11) . . ?
C38 C37 C35 109.28(11) . . ?
C31 C37 C35 101.95(10) . . ?
C38 C37 H37 109.0 . . ?
C31 C37 H37 109.0 . . ?
C35 C37 H37 109.0 . . ?
O4 C38 N8 120.54(12) . . ?
O4 C38 C37 116.55(12) . . ?
N8 C38 C37 122.91(12) . . ?
C39 O5 H5 107.7(14) . . ?
O5 C39 C40 110.03(15) . . ?
O5 C39 H39A 109.7 . . ?
C40 C39 H39A 109.7 . . ?
O5 C39 H39B 109.7 . . ?
C40 C39 H39B 109.7 . . ?
H39A C39 H39B 108.2 . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C41 O6 H6A 108.3(13) . . ?
O6 C41 C42 112.98(14) . . ?
O6 C41 H41A 109.0 . . ?
C42 C41 H41A 109.0 . . ?
O6 C41 H41B 109.0 . . ?
C42 C41 H41B 109.0 . . ?
H41A C41 H41B 107.8 . . ?
C41 C42 H42A 109.5 . . ?
C41 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C41 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?

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
C6 H6 N4 0.95 2.49 2.9668(17) 111.1 . yes
C29 H29A O1 0.98 2.45 3.3465(18) 151.9 1_545 yes
O6 H6A O4 0.88(2) 1.89(2) 2.7447(15) 163.5(19) . yes
O5 H5 O2 0.90(2) 1.87(2) 2.7479(15) 166(2) . yes

_refine_diff_density_max         0.424
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.050

####################################################################### 
# 
# 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_11d_amis19
_database_code_depnum_ccdc_archive 'CCDC 1980578'
loop_
_audit_author_name
_audit_author_address
'Matti Haukka'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2020-01-29 deposited with the CCDC.	2020-08-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H21 N5 O2'
_chemical_formula_sum            'C24 H21 N5 O2'
_chemical_formula_weight         411.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   15.91340(10)
_cell_length_b                   8.38680(10)
_cell_length_c                   16.48080(10)
_cell_angle_alpha                90
_cell_angle_beta                 113.8600(10)
_cell_angle_gamma                90
_cell_volume                     2011.59(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    35514
_cell_measurement_theta_min      2.8700
_cell_measurement_theta_max      76.4470

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_F_000             864
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.142
_exptl_crystal_size_mid          0.101
_exptl_crystal_size_min          0.072
_exptl_absorpt_coefficient_mu    0.725
_shelx_estimated_absorpt_T_min   0.904
_shelx_estimated_absorpt_T_max   0.950
_exptl_absorpt_correction_T_min  0.987
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'φ scans and ω scans with κ offset'
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_detector_area_resol_mean 10.3953
_diffrn_reflns_number            55685
_diffrn_reflns_av_unetI/netI     0.0104
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         5.006
_diffrn_reflns_theta_max         76.865
_diffrn_reflns_theta_full        67.684
_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             4250
_reflns_number_gt                4024
_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 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
;
_computing_cell_refinement       
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
;
_computing_data_reduction        
;
CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019)
;
_computing_structure_solution    'SHELXT (Sheldrick, 2017)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    
'CrystaMaker X (CrystalMaker Software ltd., 2019)'
_computing_publication_material  'SHELXL-2017/1 (Sheldrick, 2017)'
_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)+(0.0533P)²+0.6805P] 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         4250
_refine_ls_number_parameters     285
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.0996
_refine_ls_wR_factor_gt          0.0978
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_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
O1 O 0.41530(6) 0.62931(11) 0.62119(6) 0.0358(2) Uani 1 1 d . . . . .
O2 O 0.46851(6) 0.83226(9) 1.02716(5) 0.02872(18) Uani 1 1 d . . . . .
N1 N 0.24664(6) 0.60673(11) 0.77940(6) 0.0241(2) Uani 1 1 d . . . . .
N2 N 0.24253(6) 0.55431(12) 0.69866(6) 0.0252(2) Uani 1 1 d . . . . .
N3 N 0.37861(6) 0.66342(11) 0.77814(5) 0.02185(19) Uani 1 1 d . . . . .
N4 N 0.29426(6) 0.45392(11) 0.56417(6) 0.02323(19) Uani 1 1 d . . . . .
N5 N 0.35024(6) 0.73795(11) 0.90755(6) 0.02299(19) Uani 1 1 d . . . . .
C1 C 0.32259(7) 0.58961(13) 0.69993(7) 0.0231(2) Uani 1 1 d . . . . .
C2 C 0.32861(7) 0.67622(12) 0.82839(7) 0.0215(2) Uani 1 1 d . . . . .
C3 C 0.34942(7) 0.55883(13) 0.62418(7) 0.0244(2) Uani 1 1 d . . . . .
C4 C 0.30155(7) 0.40354(14) 0.48519(7) 0.0247(2) Uani 1 1 d . . . . .
C5 C 0.23918(8) 0.28853(14) 0.43505(7) 0.0286(2) Uani 1 1 d . . . . .
H5 H 0.193463 0.250244 0.453427 0.034 Uiso 1 1 calc R U . . .
C6 C 0.24366(8) 0.22971(16) 0.35830(8) 0.0339(3) Uani 1 1 d . . . . .
H6 H 0.201676 0.149729 0.324820 0.041 Uiso 1 1 calc R U . . .
C7 C 0.30897(10) 0.2869(2) 0.33023(9) 0.0463(4) Uani 1 1 d . . . . .
H7 H 0.311680 0.247464 0.277308 0.056 Uiso 1 1 calc R U . . .
C8 C 0.37008(11) 0.4018(3) 0.37988(10) 0.0609(5) Uani 1 1 d . . . . .
H8 H 0.414866 0.441296 0.360555 0.073 Uiso 1 1 calc R U . . .
C9 C 0.36756(10) 0.4613(2) 0.45769(9) 0.0460(4) Uani 1 1 d . . . . .
H9 H 0.410283 0.540115 0.491445 0.055 Uiso 1 1 calc R U . . .
C10 C 0.46842(7) 0.74323(13) 0.80470(7) 0.0230(2) Uani 1 1 d . . . . .
H10 H 0.464297 0.823600 0.758419 0.028 Uiso 1 1 calc R U . . .
C11 C 0.55234(7) 0.63256(14) 0.82129(7) 0.0273(2) Uani 1 1 d . . . . .
H11 H 0.555886 0.583703 0.767419 0.033 Uiso 1 1 calc R U . . .
C12 C 0.62858(8) 0.75376(15) 0.87254(8) 0.0316(3) Uani 1 1 d . . . . .
H12A H 0.691116 0.708009 0.892830 0.038 Uiso 1 1 calc R U . . .
H12B H 0.624383 0.853449 0.838947 0.038 Uiso 1 1 calc R U . . .
C13 C 0.59638(7) 0.77435(15) 0.94808(7) 0.0292(2) Uani 1 1 d . . . . .
H13 H 0.635435 0.843843 0.998576 0.035 Uiso 1 1 calc R U . . .
C14 C 0.49512(7) 0.83049(13) 0.89536(7) 0.0241(2) Uani 1 1 d . . . . .
H14 H 0.495541 0.947889 0.884922 0.029 Uiso 1 1 calc R U . . .
C15 C 0.58791(8) 0.60229(15) 0.97041(8) 0.0313(3) Uani 1 1 d . . . . .
H15 H 0.599980 0.561010 1.027739 0.038 Uiso 1 1 calc R U . . .
C16 C 0.56053(7) 0.51863(14) 0.89549(8) 0.0307(2) Uani 1 1 d . . . . .
H16 H 0.548297 0.407381 0.889588 0.037 Uiso 1 1 calc R U . . .
C17 C 0.43729(7) 0.79928(12) 0.94799(7) 0.0232(2) Uani 1 1 d . . . . .
C18 C 0.16819(7) 0.60190(13) 0.80101(7) 0.0238(2) Uani 1 1 d . . . . .
C19 C 0.17644(8) 0.53582(15) 0.88093(7) 0.0293(2) Uani 1 1 d . . . . .
H19 H 0.232831 0.489582 0.919961 0.035 Uiso 1 1 calc R U . . .
C20 C 0.10133(8) 0.53815(16) 0.90307(8) 0.0326(3) Uani 1 1 d . . . . .
H20 H 0.106712 0.493479 0.957926 0.039 Uiso 1 1 calc R U . . .
C21 C 0.01810(8) 0.60466(15) 0.84652(8) 0.0320(3) Uani 1 1 d . . . . .
C22 C -0.06221(10) 0.6097(2) 0.87295(10) 0.0494(4) Uani 1 1 d . . . . .
H22A H -0.050540 0.689447 0.919733 0.074 Uiso 1 1 calc R U . . .
H22B H -0.070152 0.504714 0.894996 0.074 Uiso 1 1 calc R U . . .
H22C H -0.118100 0.638212 0.821304 0.074 Uiso 1 1 calc R U . . .
C23 C 0.01143(8) 0.66669(15) 0.76581(8) 0.0322(3) Uani 1 1 d . . . . .
H23 H -0.045467 0.709712 0.725718 0.039 Uiso 1 1 calc R U . . .
C24 C 0.08619(8) 0.66703(14) 0.74265(7) 0.0277(2) Uani 1 1 d . . . . .
H24 H 0.081081 0.711177 0.687758 0.033 Uiso 1 1 calc R U . . .
H4 H 0.2510(11) 0.4059(19) 0.5761(10) 0.038(4) 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 C3 1.2217(13) . yes
O2 C17 1.2253(13) . yes
N1 C2 1.3569(14) . yes
N1 N2 1.3775(12) . yes
N1 C18 1.4306(13) . yes
N2 C1 1.2999(14) . yes
N3 C2 1.3652(13) . yes
N3 C1 1.3819(13) . yes
N3 C10 1.4752(13) . yes
N4 C3 1.3493(14) . yes
N4 C4 1.4172(13) . yes
N4 H4 0.886(16) . yes
N5 C2 1.3135(13) . yes
N5 C17 1.3714(14) . yes
C1 C3 1.4962(14) . ?
C4 C9 1.3887(16) . ?
C4 C5 1.3910(16) . ?
C5 C6 1.3861(15) . ?
C5 H5 0.9500 . ?
C6 C7 1.3833(18) . ?
C6 H6 0.9500 . ?
C7 C8 1.379(2) . ?
C7 H7 0.9500 . ?
C8 C9 1.3917(17) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.5570(15) . ?
C10 C14 1.5604(14) . ?
C10 H10 1.0000 . ?
C11 C16 1.5154(16) . ?
C11 C12 1.5459(16) . ?
C11 H11 1.0000 . ?
C12 C13 1.5358(15) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C15 1.5087(17) . ?
C13 C14 1.5622(15) . ?
C13 H13 1.0000 . ?
C14 C17 1.5211(14) . ?
C14 H14 1.0000 . ?
C15 C16 1.3310(17) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C18 C24 1.3823(15) . ?
C18 C19 1.3855(15) . ?
C19 C20 1.3837(16) . ?
C19 H19 0.9500 . ?
C20 C21 1.3912(17) . ?
C20 H20 0.9500 . ?
C21 C23 1.3918(17) . ?
C21 C22 1.5083(16) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.3887(16) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 N2 111.75(8) . . ?
C2 N1 C18 126.13(9) . . ?
N2 N1 C18 121.75(8) . . ?
C1 N2 N1 104.39(8) . . ?
C2 N3 C1 106.66(8) . . ?
C2 N3 C10 121.12(8) . . ?
C1 N3 C10 131.46(8) . . ?
C3 N4 C4 126.66(9) . . ?
C3 N4 H4 117.9(10) . . ?
C4 N4 H4 115.4(10) . . ?
C2 N5 C17 115.97(9) . . ?
N2 C1 N3 112.04(9) . . ?
N2 C1 C3 123.77(9) . . ?
N3 C1 C3 124.15(9) . . ?
N5 C2 N1 124.26(9) . . ?
N5 C2 N3 130.59(10) . . ?
N1 C2 N3 105.14(8) . . ?
O1 C3 N4 126.89(10) . . ?
O1 C3 C1 119.30(10) . . ?
N4 C3 C1 113.80(9) . . ?
C9 C4 C5 120.01(10) . . ?
C9 C4 N4 123.33(10) . . ?
C5 C4 N4 116.65(9) . . ?
C6 C5 C4 120.09(11) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C7 C6 C5 120.31(12) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C8 C7 C6 119.28(11) . . ?
C8 C7 H7 120.4 . . ?
C6 C7 H7 120.4 . . ?
C7 C8 C9 121.41(13) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C4 C9 C8 118.90(12) . . ?
C4 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
N3 C10 C11 116.15(9) . . ?
N3 C10 C14 110.66(8) . . ?
C11 C10 C14 103.26(8) . . ?
N3 C10 H10 108.8 . . ?
C11 C10 H10 108.8 . . ?
C14 C10 H10 108.8 . . ?
C16 C11 C12 100.45(9) . . ?
C16 C11 C10 107.77(8) . . ?
C12 C11 C10 97.57(9) . . ?
C16 C11 H11 116.2 . . ?
C12 C11 H11 116.2 . . ?
C10 C11 H11 116.2 . . ?
C13 C12 C11 94.09(8) . . ?
C13 C12 H12A 112.9 . . ?
C11 C12 H12A 112.9 . . ?
C13 C12 H12B 112.9 . . ?
C11 C12 H12B 112.9 . . ?
H12A C12 H12B 110.3 . . ?
C15 C13 C12 100.50(10) . . ?
C15 C13 C14 104.49(9) . . ?
C12 C13 C14 100.97(9) . . ?
C15 C13 H13 116.2 . . ?
C12 C13 H13 116.2 . . ?
C14 C13 H13 116.2 . . ?
C17 C14 C10 118.17(9) . . ?
C17 C14 C13 110.91(9) . . ?
C10 C14 C13 102.20(8) . . ?
C17 C14 H14 108.4 . . ?
C10 C14 H14 108.4 . . ?
C13 C14 H14 108.4 . . ?
C16 C15 C13 107.82(10) . . ?
C16 C15 H15 126.1 . . ?
C13 C15 H15 126.1 . . ?
C15 C16 C11 107.77(10) . . ?
C15 C16 H16 126.1 . . ?
C11 C16 H16 126.1 . . ?
O2 C17 N5 119.80(10) . . ?
O2 C17 C14 119.35(10) . . ?
N5 C17 C14 120.84(9) . . ?
C24 C18 C19 121.29(10) . . ?
C24 C18 N1 119.26(9) . . ?
C19 C18 N1 119.43(10) . . ?
C20 C19 C18 119.03(10) . . ?
C20 C19 H19 120.5 . . ?
C18 C19 H19 120.5 . . ?
C19 C20 C21 121.26(11) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C20 C21 C23 118.29(10) . . ?
C20 C21 C22 120.40(11) . . ?
C23 C21 C22 121.30(11) . . ?
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 . . ?
C24 C23 C21 121.39(11) . . ?
C24 C23 H23 119.3 . . ?
C21 C23 H23 119.3 . . ?
C18 C24 C23 118.72(10) . . ?
C18 C24 H24 120.6 . . ?
C23 C24 H24 120.6 . . ?

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
C2 N1 N2 C1 1.17(12) . . . . ?
C18 N1 N2 C1 174.55(9) . . . . ?
N1 N2 C1 N3 -0.20(12) . . . . ?
N1 N2 C1 C3 -178.22(10) . . . . ?
C2 N3 C1 N2 -0.80(12) . . . . ?
C10 N3 C1 N2 -170.56(10) . . . . ?
C2 N3 C1 C3 177.21(10) . . . . ?
C10 N3 C1 C3 7.45(18) . . . . ?
C17 N5 C2 N1 178.32(10) . . . . ?
C17 N5 C2 N3 -0.58(16) . . . . ?
N2 N1 C2 N5 179.22(10) . . . . ?
C18 N1 C2 N5 6.19(17) . . . . ?
N2 N1 C2 N3 -1.65(12) . . . . ?
C18 N1 C2 N3 -174.68(10) . . . . ?
C1 N3 C2 N5 -179.51(11) . . . . ?
C10 N3 C2 N5 -8.46(17) . . . . ?
C1 N3 C2 N1 1.44(11) . . . . ?
C10 N3 C2 N1 172.48(9) . . . . ?
C4 N4 C3 O1 0.13(19) . . . . ?
C4 N4 C3 C1 178.88(10) . . . . ?
N2 C1 C3 O1 161.87(11) . . . . ?
N3 C1 C3 O1 -15.91(17) . . . . ?
N2 C1 C3 N4 -16.98(16) . . . . ?
N3 C1 C3 N4 165.24(10) . . . . ?
C3 N4 C4 C9 -1.75(19) . . . . ?
C3 N4 C4 C5 177.25(11) . . . . ?
C9 C4 C5 C6 0.95(19) . . . . ?
N4 C4 C5 C6 -178.08(11) . . . . ?
C4 C5 C6 C7 -1.2(2) . . . . ?
C5 C6 C7 C8 0.6(2) . . . . ?
C6 C7 C8 C9 0.1(3) . . . . ?
C5 C4 C9 C8 -0.2(2) . . . . ?
N4 C4 C9 C8 178.76(14) . . . . ?
C7 C8 C9 C4 -0.3(3) . . . . ?
C2 N3 C10 C11 119.77(10) . . . . ?
C1 N3 C10 C11 -71.70(14) . . . . ?
C2 N3 C10 C14 2.49(13) . . . . ?
C1 N3 C10 C14 171.02(10) . . . . ?
N3 C10 C11 C16 -60.23(11) . . . . ?
C14 C10 C11 C16 61.08(11) . . . . ?
N3 C10 C11 C12 -163.81(9) . . . . ?
C14 C10 C11 C12 -42.50(10) . . . . ?
C16 C11 C12 C13 -48.63(10) . . . . ?
C10 C11 C12 C13 61.10(9) . . . . ?
C11 C12 C13 C15 49.54(10) . . . . ?
C11 C12 C13 C14 -57.62(10) . . . . ?
N3 C10 C14 C17 9.94(13) . . . . ?
C11 C10 C14 C17 -115.01(10) . . . . ?
N3 C10 C14 C13 131.94(9) . . . . ?
C11 C10 C14 C13 6.99(10) . . . . ?
C15 C13 C14 C17 54.34(11) . . . . ?
C12 C13 C14 C17 158.33(9) . . . . ?
C15 C13 C14 C10 -72.51(10) . . . . ?
C12 C13 C14 C10 31.49(10) . . . . ?
C12 C13 C15 C16 -34.04(11) . . . . ?
C14 C13 C15 C16 70.30(11) . . . . ?
C13 C15 C16 C11 1.43(12) . . . . ?
C12 C11 C16 C15 31.44(11) . . . . ?
C10 C11 C16 C15 -70.09(11) . . . . ?
C2 N5 C17 O2 -166.79(10) . . . . ?
C2 N5 C17 C14 14.57(14) . . . . ?
C10 C14 C17 O2 161.85(10) . . . . ?
C13 C14 C17 O2 44.39(13) . . . . ?
C10 C14 C17 N5 -19.50(14) . . . . ?
C13 C14 C17 N5 -136.96(10) . . . . ?
C2 N1 C18 C24 121.27(12) . . . . ?
N2 N1 C18 C24 -51.11(15) . . . . ?
C2 N1 C18 C19 -57.08(15) . . . . ?
N2 N1 C18 C19 130.53(11) . . . . ?
C24 C18 C19 C20 -1.22(18) . . . . ?
N1 C18 C19 C20 177.11(10) . . . . ?
C18 C19 C20 C21 0.32(19) . . . . ?
C19 C20 C21 C23 1.17(19) . . . . ?
C19 C20 C21 C22 -178.45(13) . . . . ?
C20 C21 C23 C24 -1.82(19) . . . . ?
C22 C21 C23 C24 177.80(13) . . . . ?
C19 C18 C24 C23 0.59(17) . . . . ?
N1 C18 C24 C23 -177.74(10) . . . . ?
C21 C23 C24 C18 0.96(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
C9 H9 O1 0.95 2.24 2.8577(15) 122.2 . yes
C14 H14 O2 1.00 2.27 3.0607(13) 135.0 3_677 yes
N4 H4 N5 0.886(16) 2.236(17) 3.1068(12) 167.3(14) 2_546 yes

_refine_diff_density_max         0.249
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.038

