# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2215944'
loop_
_audit_author_name
_audit_author_address
'Edward R.T. Tiekink'
;Sunway University
Malaysia
;
_audit_update_record             
;
2022-10-28 deposited with the CCDC.	2022-12-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H21 N5 O4'
_chemical_formula_sum            'C19 H21 N5 O4'
_chemical_formula_weight         383.41

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/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                   18.40122(19)
_cell_length_b                   17.9816(2)
_cell_length_c                   22.5030(3)
_cell_angle_alpha                90
_cell_angle_beta                 103.6700(11)
_cell_angle_gamma                90
_cell_volume                     7234.95(15)
_cell_formula_units_Z            16
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    28678
_cell_measurement_theta_min      4.0380
_cell_measurement_theta_max      76.3710

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_F_000             3232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.096
_exptl_crystal_size_mid          0.078
_exptl_crystal_size_min          0.042
_exptl_absorpt_coefficient_mu    0.841
_shelx_estimated_absorpt_T_min   0.924
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.867
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'CrysAlisPro (Rigaku OD, 2017)'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.2558
_diffrn_reflns_number            87869
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_av_R_equivalents  0.0459
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.182
_diffrn_reflns_theta_max         67.118
_diffrn_reflns_theta_full        67.118
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             12926
_reflns_number_gt                10991
_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 (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXS (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_refine_special_details          
;
Owing to poor agreement, one reflection, i.e. (11 2 14), was omitted from
the final cycles of refinement.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0517P)²+2.2905P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         12926
_refine_ls_number_parameters     1062
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0384
_refine_ls_wR_factor_ref         0.1053
_refine_ls_wR_factor_gt          0.0995
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
O1A O 0.59654(5) 0.42620(5) 0.20181(4) 0.0230(2) Uani 1 1 d . . . . .
O1B O 0.07228(6) 1.12177(5) 0.21395(4) 0.0275(2) Uani 1 1 d . . . . .
O1C O 0.61915(5) 0.57411(5) 0.77453(4) 0.0234(2) Uani 1 1 d . . . . .
O1D O 0.86024(6) 0.38020(6) 0.74712(5) 0.0304(2) Uani 1 1 d . . . . .
O2A O 0.49198(5) 0.34970(5) 0.12540(4) 0.0230(2) Uani 1 1 d . . . . .
O2B O -0.01733(5) 1.04311(6) 0.12825(4) 0.0226(2) Uani 1 1 d . . . . .
O2C O 0.72661(5) 0.65258(5) 0.84648(4) 0.0228(2) Uani 1 1 d . . . . .
O2D O 0.76842(5) 0.45812(5) 0.66226(4) 0.0228(2) Uani 1 1 d . . . . .
O3A O 0.47746(5) 0.20085(5) 0.13711(4) 0.0245(2) Uani 1 1 d . . . . .
O3B O -0.00929(5) 0.89259(6) 0.12602(4) 0.0258(2) Uani 1 1 d . . . . .
O3C O 0.74086(5) 0.79876(6) 0.83261(4) 0.0266(2) Uani 1 1 d . . . . .
O3D O 0.78210(6) 0.60529(6) 0.65263(5) 0.0306(2) Uani 1 1 d . . . . .
O4A O 0.82130(6) 0.55435(6) 0.47387(5) 0.0273(2) Uani 1 1 d . . . . .
O4B O 0.32421(5) 1.24156(5) 0.48445(4) 0.0243(2) Uani 1 1 d . . . . .
O4C O 0.38991(5) 0.44238(5) 0.50615(4) 0.0245(2) Uani 1 1 d . . . . .
O4D O 1.11329(6) 0.25933(5) 0.99829(5) 0.0264(2) Uani 1 1 d . . . . .
N1A N 0.77661(6) 0.13108(7) 0.41555(5) 0.0226(2) Uani 1 1 d . . . . .
H1N H 0.7704(8) -0.0031(9) 0.3993(7) 0.027 Uiso 1 1 d D U . . .
H2N H 0.7056(9) -0.0085(9) 0.3412(7) 0.027 Uiso 1 1 d D U . . .
N1B N 0.29136(6) 0.82281(6) 0.40231(5) 0.0190(2) Uani 1 1 d . . . . .
H4N H 0.2823(8) 0.6911(9) 0.3830(7) 0.023 Uiso 1 1 d D U . . .
H5N H 0.2202(8) 0.6868(9) 0.3251(7) 0.023 Uiso 1 1 d D U . . .
N1C N 0.42658(6) 0.86717(6) 0.56396(5) 0.0204(2) Uani 1 1 d . . . . .
H7N H 0.4413(8) 0.9992(9) 0.5770(7) 0.024 Uiso 1 1 d D U . . .
H8N H 0.5038(9) 1.0056(10) 0.6347(8) 0.039(5) Uiso 1 1 d D . . . .
N1D N 1.09380(6) 0.67911(6) 0.92084(5) 0.0196(2) Uani 1 1 d . . . . .
H10N H 1.0869(8) 0.8098(9) 0.8995(7) 0.023 Uiso 1 1 d D U . . .
H11N H 1.0248(8) 0.8147(9) 0.8425(7) 0.023 Uiso 1 1 d D U . . .
N2A N 0.73736(7) 0.01994(7) 0.36847(6) 0.0261(3) Uani 1 1 d D . . . .
N2B N 0.24993(7) 0.71271(7) 0.35438(6) 0.0225(2) Uani 1 1 d D . . . .
N2C N 0.47252(7) 0.97898(7) 0.60679(6) 0.0267(3) Uani 1 1 d D . . . .
N2D N 1.05581(7) 0.78857(7) 0.87012(6) 0.0240(3) Uani 1 1 d D . . . .
N3A N 0.68292(6) 0.12565(6) 0.32129(5) 0.0216(2) Uani 1 1 d . . . . .
N3B N 0.19649(6) 0.81960(6) 0.30859(5) 0.0188(2) Uani 1 1 d . . . . .
N3C N 0.52115(6) 0.87358(6) 0.65798(5) 0.0202(2) Uani 1 1 d . . . . .
N3D N 1.00048(6) 0.68152(6) 0.82599(5) 0.0195(2) Uani 1 1 d . . . . .
N5A N 0.72594(6) 0.24290(6) 0.36472(5) 0.0214(2) Uani 1 1 d . . . . .
N5B N 0.23812(6) 0.93602(6) 0.35490(5) 0.0194(2) Uani 1 1 d . . . . .
N5C N 0.47837(6) 0.75572(6) 0.61517(5) 0.0200(2) Uani 1 1 d . . . . .
N5D N 1.03741(6) 0.56599(6) 0.87579(5) 0.0186(2) Uani 1 1 d . . . . .
N6A N 0.81248(7) 0.24548(7) 0.45756(5) 0.0247(3) Uani 1 1 d D . . . .
H3N H 0.8355(9) 0.2211(9) 0.4919(7) 0.030 Uiso 1 1 d D U . . .
N6B N 0.33025(7) 0.93595(7) 0.44508(5) 0.0226(3) Uani 1 1 d D . . . .
H6N H 0.3528(9) 0.9105(9) 0.4773(7) 0.027 Uiso 1 1 d D U . . .
N6C N 0.38784(6) 0.75185(6) 0.52461(5) 0.0207(2) Uani 1 1 d D . . . .
H9N H 0.3622(9) 0.7762(9) 0.4928(7) 0.025 Uiso 1 1 d D U . . .
N6D N 1.12326(6) 0.56649(6) 0.96873(5) 0.0220(2) Uani 1 1 d D . . . .
H12N H 1.1493(9) 0.5918(9) 1.0032(7) 0.026 Uiso 1 1 d D U . . .
C2A C 0.73211(8) 0.09443(8) 0.36876(6) 0.0212(3) Uani 1 1 d . . . . .
C2B C 0.24617(7) 0.78709(8) 0.35527(6) 0.0183(3) Uani 1 1 d . . . . .
C2C C 0.47314(7) 0.90465(8) 0.60939(6) 0.0203(3) Uani 1 1 d . . . . .
C2D C 1.05054(7) 0.71442(8) 0.87227(6) 0.0188(3) Uani 1 1 d . . . . .
C4A C 0.68377(7) 0.19990(8) 0.32165(6) 0.0193(3) Uani 1 1 d . . . . .
C4B C 0.19511(7) 0.89357(7) 0.31179(6) 0.0169(3) Uani 1 1 d . . . . .
C4C C 0.52107(7) 0.79946(8) 0.65739(6) 0.0185(3) Uani 1 1 d . . . . .
C4D C 0.99727(7) 0.60757(8) 0.83063(6) 0.0180(3) Uani 1 1 d . . . . .
C6A C 0.77024(7) 0.20547(8) 0.41120(6) 0.0205(3) Uani 1 1 d . . . . .
C6B C 0.28516(7) 0.89732(8) 0.39917(6) 0.0192(3) Uani 1 1 d . . . . .
C6C C 0.43210(7) 0.79279(8) 0.56960(6) 0.0188(3) Uani 1 1 d . . . . .
C6D C 1.08424(7) 0.60493(7) 0.92012(6) 0.0184(3) Uani 1 1 d . . . . .
C41A C 0.63367(7) 0.23886(8) 0.26943(6) 0.0192(3) Uani 1 1 d . . . . .
C41B C 0.14044(7) 0.93328(8) 0.26266(6) 0.0176(3) Uani 1 1 d . . . . .
C41C C 0.57454(7) 0.76070(8) 0.70792(6) 0.0187(3) Uani 1 1 d . . . . .
C41D C 0.94113(7) 0.56704(8) 0.78306(6) 0.0195(3) Uani 1 1 d . . . . .
C42A C 0.64121(7) 0.31546(8) 0.26258(6) 0.0197(3) Uani 1 1 d . . . . .
H42A H 0.677730 0.342768 0.291185 0.024 Uiso 1 1 calc R U . . .
C42B C 0.13552(7) 1.01056(8) 0.26320(6) 0.0193(3) Uani 1 1 d . . . . .
H42B H 0.167993 1.038601 0.294265 0.023 Uiso 1 1 calc R U . . .
C42C C 0.56816(7) 0.68452(8) 0.71570(6) 0.0194(3) Uani 1 1 d . . . . .
H42C H 0.529424 0.657171 0.689299 0.023 Uiso 1 1 calc R U . . .
C42D C 0.93278(7) 0.49062(8) 0.78821(6) 0.0210(3) Uani 1 1 d . . . . .
H42D H 0.965573 0.463484 0.819712 0.025 Uiso 1 1 calc R U . . .
C43A C 0.59439(7) 0.35117(7) 0.21319(6) 0.0190(3) Uani 1 1 d . . . . .
C43B C 0.08265(7) 1.04618(8) 0.21787(6) 0.0198(3) Uani 1 1 d . . . . .
C43C C 0.61897(7) 0.64871(7) 0.76246(6) 0.0190(3) Uani 1 1 d . . . . .
C43D C 0.87585(8) 0.45445(8) 0.74667(6) 0.0213(3) Uani 1 1 d . . . . .
C44A C 0.53979(7) 0.31156(8) 0.17156(6) 0.0195(3) Uani 1 1 d . . . . .
C44B C 0.03537(7) 1.00567(8) 0.17155(6) 0.0192(3) Uani 1 1 d . . . . .
C44C C 0.67622(7) 0.68898(8) 0.80086(6) 0.0188(3) Uani 1 1 d . . . . .
C44D C 0.82703(7) 0.49435(8) 0.70091(6) 0.0210(3) Uani 1 1 d . . . . .
C45A C 0.53296(7) 0.23518(8) 0.17957(6) 0.0203(3) Uani 1 1 d . . . . .
C45B C 0.04042(7) 0.92838(8) 0.17189(6) 0.0199(3) Uani 1 1 d . . . . .
C45C C 0.68220(7) 0.76533(8) 0.79274(6) 0.0202(3) Uani 1 1 d . . . . .
C45D C 0.83603(8) 0.57061(8) 0.69633(6) 0.0233(3) Uani 1 1 d . . . . .
C46A C 0.58006(7) 0.19886(8) 0.22801(6) 0.0204(3) Uani 1 1 d . . . . .
H46A H 0.575665 0.146697 0.232850 0.024 Uiso 1 1 calc R U . . .
C46B C 0.09280(7) 0.89225(8) 0.21726(6) 0.0190(3) Uani 1 1 d . . . . .
H46B H 0.096083 0.839520 0.217287 0.023 Uiso 1 1 calc R U . . .
C46C C 0.63150(7) 0.80154(8) 0.74638(6) 0.0195(3) Uani 1 1 d . . . . .
H46C H 0.635393 0.853625 0.740771 0.023 Uiso 1 1 calc R U . . .
C46D C 0.89424(8) 0.60684(8) 0.73631(6) 0.0229(3) Uani 1 1 d . . . . .
H46D H 0.902015 0.658557 0.731778 0.028 Uiso 1 1 calc R U . . .
C47A C 0.64521(8) 0.47042(8) 0.24701(6) 0.0248(3) Uani 1 1 d . . . . .
H47A H 0.633815 0.462087 0.286880 0.037 Uiso 1 1 calc R U . . .
H47B H 0.637982 0.523085 0.236006 0.037 Uiso 1 1 calc R U . . .
H47C H 0.697242 0.456423 0.249165 0.037 Uiso 1 1 calc R U . . .
C47B C 0.11404(10) 1.16572(9) 0.26272(8) 0.0389(4) Uani 1 1 d . . . . .
H47D H 0.104848 1.148182 0.301523 0.058 Uiso 1 1 calc R U . . .
H47E H 0.098597 1.217841 0.256332 0.058 Uiso 1 1 calc R U . . .
H47F H 0.167463 1.161445 0.263924 0.058 Uiso 1 1 calc R U . . .
C47C C 0.55673(8) 0.53183(8) 0.74202(7) 0.0273(3) Uani 1 1 d . . . . .
H47G H 0.510409 0.553731 0.748426 0.041 Uiso 1 1 calc R U . . .
H47H H 0.561217 0.480478 0.757029 0.041 Uiso 1 1 calc R U . . .
H47I H 0.555685 0.532247 0.698280 0.041 Uiso 1 1 calc R U . . .
C47D C 0.90098(11) 0.33758(9) 0.79747(9) 0.0496(5) Uani 1 1 d . . . . .
H47J H 0.953737 0.335422 0.795994 0.074 Uiso 1 1 calc R U . . .
H47K H 0.880499 0.287071 0.795201 0.074 Uiso 1 1 calc R U . . .
H47L H 0.896706 0.360943 0.835847 0.074 Uiso 1 1 calc R U . . .
C48A C 0.50558(8) 0.33628(9) 0.06598(6) 0.0247(3) Uani 1 1 d . . . . .
H48A H 0.559449 0.338629 0.068577 0.037 Uiso 1 1 calc R U . . .
H48B H 0.479862 0.374141 0.037278 0.037 Uiso 1 1 calc R U . . .
H48C H 0.486704 0.286907 0.051596 0.037 Uiso 1 1 calc R U . . .
C48B C -0.00241(8) 1.04125(8) 0.06857(6) 0.0249(3) Uani 1 1 d . . . . .
H48D H 0.049422 1.056475 0.071327 0.037 Uiso 1 1 calc R U . . .
H48E H -0.036427 1.075374 0.041448 0.037 Uiso 1 1 calc R U . . .
H48F H -0.010008 0.990629 0.052140 0.037 Uiso 1 1 calc R U . . .
C48C C 0.79297(8) 0.63507(9) 0.82637(8) 0.0336(4) Uani 1 1 d . . . . .
H48G H 0.779905 0.603652 0.789804 0.050 Uiso 1 1 calc R U . . .
H48H H 0.828168 0.608447 0.858899 0.050 Uiso 1 1 calc R U . . .
H48I H 0.816183 0.681129 0.816660 0.050 Uiso 1 1 calc R U . . .
C48D C 0.70387(8) 0.45680(9) 0.68796(7) 0.0287(3) Uani 1 1 d . . . . .
H48J H 0.717550 0.435109 0.729050 0.043 Uiso 1 1 calc R U . . .
H48K H 0.664456 0.426754 0.661927 0.043 Uiso 1 1 calc R U . . .
H48L H 0.685641 0.507656 0.690414 0.043 Uiso 1 1 calc R U . . .
C49A C 0.46752(8) 0.12350(8) 0.14530(7) 0.0260(3) Uani 1 1 d . . . . .
H49A H 0.513399 0.096913 0.143371 0.039 Uiso 1 1 calc R U . . .
H49B H 0.425932 0.105250 0.112933 0.039 Uiso 1 1 calc R U . . .
H49C H 0.456383 0.114972 0.185239 0.039 Uiso 1 1 calc R U . . .
C49B C -0.00645(9) 0.81341(8) 0.12624(7) 0.0317(3) Uani 1 1 d . . . . .
H49D H 0.042270 0.797057 0.120593 0.048 Uiso 1 1 calc R U . . .
H49E H -0.046178 0.793996 0.092882 0.048 Uiso 1 1 calc R U . . .
H49F H -0.013506 0.794725 0.165402 0.048 Uiso 1 1 calc R U . . .
C49C C 0.74417(9) 0.87802(8) 0.83224(7) 0.0315(3) Uani 1 1 d . . . . .
H49G H 0.750682 0.895111 0.792466 0.047 Uiso 1 1 calc R U . . .
H49H H 0.786484 0.894944 0.864564 0.047 Uiso 1 1 calc R U . . .
H49I H 0.697614 0.898451 0.839416 0.047 Uiso 1 1 calc R U . . .
C49D C 0.78339(10) 0.68443(9) 0.65064(8) 0.0361(4) Uani 1 1 d . . . . .
H49J H 0.776115 0.704508 0.689303 0.054 Uiso 1 1 calc R U . . .
H49K H 0.743205 0.702101 0.616836 0.054 Uiso 1 1 calc R U . . .
H49L H 0.831732 0.701138 0.644396 0.054 Uiso 1 1 calc R U . . .
C61A C 0.81220(7) 0.32434(8) 0.46086(6) 0.0205(3) Uani 1 1 d . . . . .
C61B C 0.32800(7) 1.01413(8) 0.45352(6) 0.0199(3) Uani 1 1 d . . . . .
C61C C 0.39146(7) 0.67296(7) 0.52061(6) 0.0188(3) Uani 1 1 d . . . . .
C61D C 1.11659(7) 0.48798(8) 0.97500(6) 0.0196(3) Uani 1 1 d . . . . .
C62A C 0.80330(7) 0.35788(8) 0.51409(6) 0.0215(3) Uani 1 1 d . . . . .
H62A H 0.795214 0.327796 0.546633 0.026 Uiso 1 1 calc R U . . .
C62B C 0.31934(7) 1.03980(8) 0.50946(6) 0.0212(3) Uani 1 1 d . . . . .
H62B H 0.313907 1.004964 0.539860 0.025 Uiso 1 1 calc R U . . .
C62C C 0.40799(7) 0.64033(8) 0.46958(6) 0.0215(3) Uani 1 1 d . . . . .
H62C H 0.419082 0.670916 0.438449 0.026 Uiso 1 1 calc R U . . .
C62D C 1.08755(8) 0.45961(8) 1.02179(6) 0.0243(3) Uani 1 1 d . . . . .
H62D H 1.070117 0.492596 1.048350 0.029 Uiso 1 1 calc R U . . .
C63A C 0.80598(7) 0.43473(8) 0.52078(6) 0.0222(3) Uani 1 1 d . . . . .
H63A H 0.800798 0.457150 0.557784 0.027 Uiso 1 1 calc R U . . .
C63B C 0.31841(7) 1.11545(8) 0.52212(6) 0.0209(3) Uani 1 1 d . . . . .
H63B H 0.313116 1.132218 0.560914 0.025 Uiso 1 1 calc R U . . .
C63C C 0.40855(8) 0.56342(8) 0.46334(6) 0.0228(3) Uani 1 1 d . . . . .
H63C H 0.419925 0.541771 0.428099 0.027 Uiso 1 1 calc R U . . .
C63D C 1.08376(8) 0.38315(8) 1.03016(7) 0.0259(3) Uani 1 1 d . . . . .
H63D H 1.063065 0.363975 1.061902 0.031 Uiso 1 1 calc R U . . .
C64A C 0.81637(7) 0.47822(8) 0.47241(6) 0.0218(3) Uani 1 1 d . . . . .
C64B C 0.32533(7) 1.16605(8) 0.47726(6) 0.0199(3) Uani 1 1 d . . . . .
C64C C 0.39252(7) 0.51837(8) 0.50853(6) 0.0201(3) Uani 1 1 d . . . . .
C64D C 1.11025(7) 0.33515(8) 0.99204(6) 0.0214(3) Uani 1 1 d . . . . .
C65A C 0.82379(7) 0.44478(8) 0.41829(6) 0.0222(3) Uani 1 1 d . . . . .
H65A H 0.829839 0.474809 0.385053 0.027 Uiso 1 1 calc R U . . .
C65B C 0.33496(7) 1.14060(8) 0.42105(6) 0.0222(3) Uani 1 1 d . . . . .
H65B H 0.340226 1.175379 0.390569 0.027 Uiso 1 1 calc R U . . .
C65C C 0.37710(7) 0.55104(8) 0.56057(6) 0.0219(3) Uani 1 1 d . . . . .
H65C H 0.367000 0.520373 0.592047 0.026 Uiso 1 1 calc R U . . .
C65D C 1.13759(7) 0.36360(8) 0.94397(6) 0.0217(3) Uani 1 1 d . . . . .
H65D H 1.154185 0.330606 0.916955 0.026 Uiso 1 1 calc R U . . .
C66A C 0.82240(7) 0.36838(8) 0.41265(6) 0.0217(3) Uani 1 1 d . . . . .
H66A H 0.828396 0.345868 0.375913 0.026 Uiso 1 1 calc R U . . .
C66B C 0.33693(7) 1.06538(8) 0.40929(6) 0.0222(3) Uani 1 1 d . . . . .
H66B H 0.344353 1.048562 0.371145 0.027 Uiso 1 1 calc R U . . .
C66C C 0.37639(7) 0.62739(8) 0.56670(6) 0.0209(3) Uani 1 1 d . . . . .
H66C H 0.365673 0.649018 0.602195 0.025 Uiso 1 1 calc R U . . .
C66D C 1.14070(7) 0.43933(8) 0.93538(6) 0.0212(3) Uani 1 1 d . . . . .
H66D H 1.159276 0.458381 0.902467 0.025 Uiso 1 1 calc R U . . .
C67A C 0.81444(9) 0.58882(9) 0.52960(7) 0.0301(3) Uani 1 1 d . . . . .
H67A H 0.765887 0.576032 0.537646 0.045 Uiso 1 1 calc R U . . .
H67B H 0.818142 0.642918 0.525900 0.045 Uiso 1 1 calc R U . . .
H67C H 0.854595 0.571131 0.563410 0.045 Uiso 1 1 calc R U . . .
C67B C 0.31297(8) 1.26815(8) 0.54177(6) 0.0252(3) Uani 1 1 d . . . . .
H67D H 0.264341 1.250961 0.547046 0.038 Uiso 1 1 calc R U . . .
H67E H 0.314161 1.322634 0.542166 0.038 Uiso 1 1 calc R U . . .
H67F H 0.352724 1.248995 0.575234 0.038 Uiso 1 1 calc R U . . .
C67C C 0.40110(8) 0.40727(8) 0.45179(7) 0.0270(3) Uani 1 1 d . . . . .
H67G H 0.362637 0.424234 0.416451 0.040 Uiso 1 1 calc R U . . .
H67H H 0.397665 0.353188 0.455779 0.040 Uiso 1 1 calc R U . . .
H67I H 0.450657 0.420388 0.445989 0.040 Uiso 1 1 calc R U . . .
C67D C 1.08341(12) 0.22741(10) 1.04543(9) 0.0452(4) Uani 1 1 d . . . . .
H67J H 1.110211 0.247186 1.085155 0.068 Uiso 1 1 calc R U . . .
H67K H 1.089296 0.173252 1.045181 0.068 Uiso 1 1 calc R U . . .
H67L H 1.030205 0.239850 1.038355 0.068 Uiso 1 1 calc R U . . .


_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
O1A C43A 1.3757(16) . ?
O1A C47A 1.4276(16) . ?
O1B C43B 1.3724(17) . ?
O1B C47B 1.4216(18) . ?
O1C C43C 1.3686(16) . ?
O1C C47C 1.4266(17) . ?
O1D C43D 1.3662(17) . ?
O1D C47D 1.4253(19) . ?
O2A C44A 1.3752(16) . ?
O2A C48A 1.4376(17) . ?
O2B C44B 1.3772(16) . ?
O2B C48B 1.4333(16) . ?
O2C C44C 1.3755(16) . ?
O2C C48C 1.4339(19) . ?
O2D C44D 1.3786(16) . ?
O2D C48D 1.4390(17) . ?
O3A C45A 1.3696(16) . ?
O3A C49A 1.4206(17) . ?
O3B C45B 1.3676(16) . ?
O3B C49B 1.4246(18) . ?
O3C C45C 1.3689(16) . ?
O3C C49C 1.4266(18) . ?
O3D C45D 1.3710(17) . ?
O3D C49D 1.4242(18) . ?
O4A C64A 1.3718(17) . ?
O4A C67A 1.4310(18) . ?
O4B C64B 1.3681(17) . ?
O4B C67B 1.4357(17) . ?
O4C C64C 1.3679(16) . ?
O4C C67C 1.4341(18) . ?
O4D C64D 1.3703(17) . ?
O4D C67D 1.426(2) . ?
N1A C2A 1.3440(18) . ?
N1A C6A 1.3444(18) . ?
N1B C2B 1.3448(17) . ?
N1B C6B 1.3452(18) . ?
N1C C6C 1.3450(18) . ?
N1C C2C 1.3489(17) . ?
N1D C6D 1.3449(18) . ?
N1D C2D 1.3492(17) . ?
N2A C2A 1.3430(19) . ?
N2A H1N 0.908(14) . ?
N2A H2N 0.901(14) . ?
N2B C2B 1.3397(18) . ?
N2B H4N 0.859(14) . ?
N2B H5N 0.884(13) . ?
N2C C2C 1.3377(19) . ?
N2C H7N 0.854(14) . ?
N2C H8N 0.886(15) . ?
N2D C2D 1.3386(18) . ?
N2D H10N 0.855(14) . ?
N2D H11N 0.875(14) . ?
N3A C4A 1.3354(18) . ?
N3A C2A 1.3485(18) . ?
N3B C4B 1.3327(17) . ?
N3B C2B 1.3516(17) . ?
N3C C4C 1.3327(18) . ?
N3C C2C 1.3534(17) . ?
N3D C4D 1.3363(18) . ?
N3D C2D 1.3525(17) . ?
N5A C4A 1.3355(18) . ?
N5A C6A 1.3448(17) . ?
N5B C4B 1.3368(17) . ?
N5B C6B 1.3484(17) . ?
N5C C4C 1.3364(17) . ?
N5C C6C 1.3446(17) . ?
N5D C4D 1.3350(17) . ?
N5D C6D 1.3498(17) . ?
N6A C6A 1.3516(18) . ?
N6A C61A 1.4201(18) . ?
N6A H3N 0.903(14) . ?
N6B C6B 1.3539(17) . ?
N6B C61B 1.4204(18) . ?
N6B H6N 0.875(14) . ?
N6C C6C 1.3567(17) . ?
N6C C61C 1.4240(17) . ?
N6C H9N 0.876(14) . ?
N6D C6D 1.3485(17) . ?
N6D C61D 1.4269(18) . ?
N6D H12N 0.928(14) . ?
C4A C41A 1.4864(18) . ?
C4B C41B 1.4896(18) . ?
C4C C41C 1.4893(18) . ?
C4D C41D 1.4905(18) . ?
C41A C46A 1.3873(19) . ?
C41A C42A 1.3965(19) . ?
C41B C46B 1.3904(18) . ?
C41B C42B 1.3926(19) . ?
C41C C42C 1.3896(19) . ?
C41C C46C 1.3992(19) . ?
C41D C46D 1.3908(19) . ?
C41D C42D 1.391(2) . ?
C42A C43A 1.3918(19) . ?
C42A H42A 0.9500 . ?
C42B C43B 1.3887(19) . ?
C42B H42B 0.9500 . ?
C42C C43C 1.3896(19) . ?
C42C H42C 0.9500 . ?
C42D C43D 1.3897(19) . ?
C42D H42D 0.9500 . ?
C43A C44A 1.3963(19) . ?
C43B C44B 1.3947(19) . ?
C43C C44C 1.3967(19) . ?
C43D C44D 1.3947(19) . ?
C44A C45A 1.3947(19) . ?
C44B C45B 1.3928(19) . ?
C44C C45C 1.393(2) . ?
C44D C45D 1.388(2) . ?
C45A C46A 1.3854(19) . ?
C45B C46B 1.3887(19) . ?
C45C C46C 1.3867(19) . ?
C45D C46D 1.388(2) . ?
C46A H46A 0.9500 . ?
C46B H46B 0.9500 . ?
C46C H46C 0.9500 . ?
C46D H46D 0.9500 . ?
C47A H47A 0.9800 . ?
C47A H47B 0.9800 . ?
C47A H47C 0.9800 . ?
C47B H47D 0.9800 . ?
C47B H47E 0.9800 . ?
C47B H47F 0.9800 . ?
C47C H47G 0.9800 . ?
C47C H47H 0.9800 . ?
C47C H47I 0.9800 . ?
C47D H47J 0.9800 . ?
C47D H47K 0.9800 . ?
C47D H47L 0.9800 . ?
C48A H48A 0.9800 . ?
C48A H48B 0.9800 . ?
C48A H48C 0.9800 . ?
C48B H48D 0.9800 . ?
C48B H48E 0.9800 . ?
C48B H48F 0.9800 . ?
C48C H48G 0.9800 . ?
C48C H48H 0.9800 . ?
C48C H48I 0.9800 . ?
C48D H48J 0.9800 . ?
C48D H48K 0.9800 . ?
C48D H48L 0.9800 . ?
C49A H49A 0.9800 . ?
C49A H49B 0.9800 . ?
C49A H49C 0.9800 . ?
C49B H49D 0.9800 . ?
C49B H49E 0.9800 . ?
C49B H49F 0.9800 . ?
C49C H49G 0.9800 . ?
C49C H49H 0.9800 . ?
C49C H49I 0.9800 . ?
C49D H49J 0.9800 . ?
C49D H49K 0.9800 . ?
C49D H49L 0.9800 . ?
C61A C62A 1.385(2) . ?
C61A C66A 1.391(2) . ?
C61B C62B 1.3849(19) . ?
C61B C66B 1.394(2) . ?
C61C C62C 1.386(2) . ?
C61C C66C 1.4001(19) . ?
C61D C62D 1.386(2) . ?
C61D C66D 1.394(2) . ?
C62A C63A 1.390(2) . ?
C62A H62A 0.9500 . ?
C62B C63B 1.391(2) . ?
C62B H62B 0.9500 . ?
C62C C63C 1.390(2) . ?
C62C H62C 0.9500 . ?
C62D C63D 1.392(2) . ?
C62D H62D 0.9500 . ?
C63A C64A 1.390(2) . ?
C63A H63A 0.9500 . ?
C63B C64B 1.387(2) . ?
C63B H63B 0.9500 . ?
C63C C64C 1.385(2) . ?
C63C H63C 0.9500 . ?
C63D C64D 1.384(2) . ?
C63D H63D 0.9500 . ?
C64A C65A 1.394(2) . ?
C64B C65B 1.395(2) . ?
C64C C65C 1.398(2) . ?
C64D C65D 1.394(2) . ?
C65A C66A 1.379(2) . ?
C65A H65A 0.9500 . ?
C65B C66B 1.380(2) . ?
C65B H65B 0.9500 . ?
C65C C66C 1.380(2) . ?
C65C H65C 0.9500 . ?
C65D C66D 1.379(2) . ?
C65D H65D 0.9500 . ?
C66A H66A 0.9500 . ?
C66B H66B 0.9500 . ?
C66C H66C 0.9500 . ?
C66D H66D 0.9500 . ?
C67A H67A 0.9800 . ?
C67A H67B 0.9800 . ?
C67A H67C 0.9800 . ?
C67B H67D 0.9800 . ?
C67B H67E 0.9800 . ?
C67B H67F 0.9800 . ?
C67C H67G 0.9800 . ?
C67C H67H 0.9800 . ?
C67C H67I 0.9800 . ?
C67D H67J 0.9800 . ?
C67D H67K 0.9800 . ?
C67D H67L 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
C43A O1A C47A 117.02(10) . . ?
C43B O1B C47B 117.35(11) . . ?
C43C O1C C47C 117.17(10) . . ?
C43D O1D C47D 117.35(11) . . ?
C44A O2A C48A 113.45(10) . . ?
C44B O2B C48B 113.13(10) . . ?
C44C O2C C48C 110.07(11) . . ?
C44D O2D C48D 110.56(10) . . ?
C45A O3A C49A 116.65(10) . . ?
C45B O3B C49B 116.76(10) . . ?
C45C O3C C49C 117.58(11) . . ?
C45D O3D C49D 117.55(11) . . ?
C64A O4A C67A 115.74(11) . . ?
C64B O4B C67B 116.50(11) . . ?
C64C O4C C67C 117.54(11) . . ?
C64D O4D C67D 117.61(12) . . ?
C2A N1A C6A 113.84(11) . . ?
C2B N1B C6B 113.91(11) . . ?
C6C N1C C2C 113.89(11) . . ?
C6D N1D C2D 113.98(11) . . ?
C2A N2A H1N 119.2(11) . . ?
C2A N2A H2N 122.3(11) . . ?
H1N N2A H2N 118.1(16) . . ?
C2B N2B H4N 118.0(11) . . ?
C2B N2B H5N 120.9(11) . . ?
H4N N2B H5N 121.1(15) . . ?
C2C N2C H7N 117.2(11) . . ?
C2C N2C H8N 120.8(13) . . ?
H7N N2C H8N 122.0(17) . . ?
C2D N2D H10N 117.2(11) . . ?
C2D N2D H11N 121.4(11) . . ?
H10N N2D H11N 121.0(16) . . ?
C4A N3A C2A 113.99(11) . . ?
C4B N3B C2B 114.05(11) . . ?
C4C N3C C2C 113.95(11) . . ?
C4D N3D C2D 114.19(11) . . ?
C4A N5A C6A 114.59(12) . . ?
C4B N5B C6B 114.08(11) . . ?
C4C N5C C6C 114.23(12) . . ?
C4D N5D C6D 114.44(11) . . ?
C6A N6A C61A 124.29(11) . . ?
C6A N6A H3N 118.1(11) . . ?
C61A N6A H3N 116.6(11) . . ?
C6B N6B C61B 125.30(11) . . ?
C6B N6B H6N 116.7(11) . . ?
C61B N6B H6N 115.5(11) . . ?
C6C N6C C61C 123.98(11) . . ?
C6C N6C H9N 116.9(11) . . ?
C61C N6C H9N 118.0(11) . . ?
C6D N6D C61D 123.06(11) . . ?
C6D N6D H12N 119.8(11) . . ?
C61D N6D H12N 116.2(10) . . ?
N2A C2A N1A 117.49(12) . . ?
N2A C2A N3A 116.54(12) . . ?
N1A C2A N3A 125.96(13) . . ?
N2B C2B N1B 117.64(12) . . ?
N2B C2B N3B 116.61(12) . . ?
N1B C2B N3B 125.74(12) . . ?
N2C C2C N1C 117.95(12) . . ?
N2C C2C N3C 116.43(12) . . ?
N1C C2C N3C 125.62(12) . . ?
N2D C2D N1D 117.65(12) . . ?
N2D C2D N3D 116.74(12) . . ?
N1D C2D N3D 125.59(12) . . ?
N3A C4A N5A 125.97(12) . . ?
N3A C4A C41A 117.53(11) . . ?
N5A C4A C41A 116.51(12) . . ?
N3B C4B N5B 126.41(12) . . ?
N3B C4B C41B 117.16(11) . . ?
N5B C4B C41B 116.43(11) . . ?
N3C C4C N5C 126.49(12) . . ?
N3C C4C C41C 117.48(11) . . ?
N5C C4C C41C 116.02(12) . . ?
N5D C4D N3D 126.16(12) . . ?
N5D C4D C41D 115.96(12) . . ?
N3D C4D C41D 117.80(11) . . ?
N1A C6A N5A 125.53(12) . . ?
N1A C6A N6A 116.68(12) . . ?
N5A C6A N6A 117.79(12) . . ?
N1B C6B N5B 125.77(12) . . ?
N1B C6B N6B 116.22(11) . . ?
N5B C6B N6B 118.01(12) . . ?
N5C C6C N1C 125.80(12) . . ?
N5C C6C N6C 117.41(12) . . ?
N1C C6C N6C 116.78(11) . . ?
N1D C6D N6D 117.10(11) . . ?
N1D C6D N5D 125.61(12) . . ?
N6D C6D N5D 117.26(12) . . ?
C46A C41A C42A 120.70(12) . . ?
C46A C41A C4A 119.77(12) . . ?
C42A C41A C4A 119.53(12) . . ?
C46B C41B C42B 120.33(12) . . ?
C46B C41B C4B 119.26(12) . . ?
C42B C41B C4B 120.38(11) . . ?
C42C C41C C46C 120.85(12) . . ?
C42C C41C C4C 119.82(12) . . ?
C46C C41C C4C 119.32(12) . . ?
C46D C41D C42D 120.70(12) . . ?
C46D C41D C4D 119.50(12) . . ?
C42D C41D C4D 119.65(12) . . ?
C43A C42A C41A 118.96(12) . . ?
C43A C42A H42A 120.5 . . ?
C41A C42A H42A 120.5 . . ?
C43B C42B C41B 119.31(12) . . ?
C43B C42B H42B 120.3 . . ?
C41B C42B H42B 120.3 . . ?
C41C C42C C43C 119.36(12) . . ?
C41C C42C H42C 120.3 . . ?
C43C C42C H42C 120.3 . . ?
C43D C42D C41D 119.14(12) . . ?
C43D C42D H42D 120.4 . . ?
C41D C42D H42D 120.4 . . ?
O1A C43A C42A 124.17(12) . . ?
O1A C43A C44A 115.03(11) . . ?
C42A C43A C44A 120.79(12) . . ?
O1B C43B C42B 124.52(12) . . ?
O1B C43B C44B 114.61(11) . . ?
C42B C43B C44B 120.86(13) . . ?
O1C C43C C42C 125.04(12) . . ?
O1C C43C C44C 114.78(11) . . ?
C42C C43C C44C 120.17(12) . . ?
O1D C43D C42D 125.36(12) . . ?
O1D C43D C44D 114.10(12) . . ?
C42D C43D C44D 120.50(13) . . ?
O2A C44A C45A 121.85(12) . . ?
O2A C44A C43A 118.87(12) . . ?
C45A C44A C43A 119.21(12) . . ?
O2B C44B C45B 121.77(12) . . ?
O2B C44B C43B 118.95(12) . . ?
C45B C44B C43B 119.21(12) . . ?
O2C C44C C45C 120.45(12) . . ?
O2C C44C C43C 119.47(12) . . ?
C45C C44C C43C 120.08(12) . . ?
O2D C44D C45D 120.63(12) . . ?
O2D C44D C43D 119.60(12) . . ?
C45D C44D C43D 119.72(12) . . ?
O3A C45A C46A 124.13(13) . . ?
O3A C45A C44A 115.38(11) . . ?
C46A C45A C44A 120.48(12) . . ?
O3B C45B C46B 123.98(12) . . ?
O3B C45B C44B 115.70(11) . . ?
C46B C45B C44B 120.31(12) . . ?
O3C C45C C46C 124.96(12) . . ?
O3C C45C C44C 114.92(11) . . ?
C46C C45C C44C 120.11(12) . . ?
O3D C45D C46D 124.64(13) . . ?
O3D C45D C44D 115.07(12) . . ?
C46D C45D C44D 120.21(12) . . ?
C45A C46A C41A 119.84(13) . . ?
C45A C46A H46A 120.1 . . ?
C41A C46A H46A 120.1 . . ?
C45B C46B C41B 119.96(12) . . ?
C45B C46B H46B 120.0 . . ?
C41B C46B H46B 120.0 . . ?
C45C C46C C41C 119.43(13) . . ?
C45C C46C H46C 120.3 . . ?
C41C C46C H46C 120.3 . . ?
C45D C46D C41D 119.64(13) . . ?
C45D C46D H46D 120.2 . . ?
C41D C46D H46D 120.2 . . ?
O1A C47A H47A 109.5 . . ?
O1A C47A H47B 109.5 . . ?
H47A C47A H47B 109.5 . . ?
O1A C47A H47C 109.5 . . ?
H47A C47A H47C 109.5 . . ?
H47B C47A H47C 109.5 . . ?
O1B C47B H47D 109.5 . . ?
O1B C47B H47E 109.5 . . ?
H47D C47B H47E 109.5 . . ?
O1B C47B H47F 109.5 . . ?
H47D C47B H47F 109.5 . . ?
H47E C47B H47F 109.5 . . ?
O1C C47C H47G 109.5 . . ?
O1C C47C H47H 109.5 . . ?
H47G C47C H47H 109.5 . . ?
O1C C47C H47I 109.5 . . ?
H47G C47C H47I 109.5 . . ?
H47H C47C H47I 109.5 . . ?
O1D C47D H47J 109.5 . . ?
O1D C47D H47K 109.5 . . ?
H47J C47D H47K 109.5 . . ?
O1D C47D H47L 109.5 . . ?
H47J C47D H47L 109.5 . . ?
H47K C47D H47L 109.5 . . ?
O2A C48A H48A 109.5 . . ?
O2A C48A H48B 109.5 . . ?
H48A C48A H48B 109.5 . . ?
O2A C48A H48C 109.5 . . ?
H48A C48A H48C 109.5 . . ?
H48B C48A H48C 109.5 . . ?
O2B C48B H48D 109.5 . . ?
O2B C48B H48E 109.5 . . ?
H48D C48B H48E 109.5 . . ?
O2B C48B H48F 109.5 . . ?
H48D C48B H48F 109.5 . . ?
H48E C48B H48F 109.5 . . ?
O2C C48C H48G 109.5 . . ?
O2C C48C H48H 109.5 . . ?
H48G C48C H48H 109.5 . . ?
O2C C48C H48I 109.5 . . ?
H48G C48C H48I 109.5 . . ?
H48H C48C H48I 109.5 . . ?
O2D C48D H48J 109.5 . . ?
O2D C48D H48K 109.5 . . ?
H48J C48D H48K 109.5 . . ?
O2D C48D H48L 109.5 . . ?
H48J C48D H48L 109.5 . . ?
H48K C48D H48L 109.5 . . ?
O3A C49A H49A 109.5 . . ?
O3A C49A H49B 109.5 . . ?
H49A C49A H49B 109.5 . . ?
O3A C49A H49C 109.5 . . ?
H49A C49A H49C 109.5 . . ?
H49B C49A H49C 109.5 . . ?
O3B C49B H49D 109.5 . . ?
O3B C49B H49E 109.5 . . ?
H49D C49B H49E 109.5 . . ?
O3B C49B H49F 109.5 . . ?
H49D C49B H49F 109.5 . . ?
H49E C49B H49F 109.5 . . ?
O3C C49C H49G 109.5 . . ?
O3C C49C H49H 109.5 . . ?
H49G C49C H49H 109.5 . . ?
O3C C49C H49I 109.5 . . ?
H49G C49C H49I 109.5 . . ?
H49H C49C H49I 109.5 . . ?
O3D C49D H49J 109.5 . . ?
O3D C49D H49K 109.5 . . ?
H49J C49D H49K 109.5 . . ?
O3D C49D H49L 109.5 . . ?
H49J C49D H49L 109.5 . . ?
H49K C49D H49L 109.5 . . ?
C62A C61A C66A 119.47(13) . . ?
C62A C61A N6A 118.87(12) . . ?
C66A C61A N6A 121.65(13) . . ?
C62B C61B C66B 119.13(13) . . ?
C62B C61B N6B 117.69(12) . . ?
C66B C61B N6B 123.13(12) . . ?
C62C C61C C66C 119.13(13) . . ?
C62C C61C N6C 119.79(12) . . ?
C66C C61C N6C 121.05(12) . . ?
C62D C61D C66D 119.54(13) . . ?
C62D C61D N6D 119.80(12) . . ?
C66D C61D N6D 120.64(13) . . ?
C61A C62A C63A 121.22(13) . . ?
C61A C62A H62A 119.4 . . ?
C63A C62A H62A 119.4 . . ?
C61B C62B C63B 121.46(13) . . ?
C61B C62B H62B 119.3 . . ?
C63B C62B H62B 119.3 . . ?
C61C C62C C63C 120.88(13) . . ?
C61C C62C H62C 119.6 . . ?
C63C C62C H62C 119.6 . . ?
C61D C62D C63D 120.48(13) . . ?
C61D C62D H62D 119.8 . . ?
C63D C62D H62D 119.8 . . ?
C62A C63A C64A 118.86(13) . . ?
C62A C63A H63A 120.6 . . ?
C64A C63A H63A 120.6 . . ?
C64B C63B C62B 119.00(12) . . ?
C64B C63B H63B 120.5 . . ?
C62B C63B H63B 120.5 . . ?
C64C C63C C62C 119.96(13) . . ?
C64C C63C H63C 120.0 . . ?
C62C C63C H63C 120.0 . . ?
C64D C63D C62D 119.72(13) . . ?
C64D C63D H63D 120.1 . . ?
C62D C63D H63D 120.1 . . ?
O4A C64A C63A 124.29(13) . . ?
O4A C64A C65A 115.58(12) . . ?
C63A C64A C65A 120.12(13) . . ?
O4B C64B C63B 123.94(12) . . ?
O4B C64B C65B 116.21(12) . . ?
C63B C64B C65B 119.85(13) . . ?
O4C C64C C63C 124.54(13) . . ?
O4C C64C C65C 116.12(12) . . ?
C63C C64C C65C 119.33(13) . . ?
O4D C64D C63D 124.64(13) . . ?
O4D C64D C65D 115.56(12) . . ?
C63D C64D C65D 119.78(13) . . ?
C66A C65A C64A 120.43(13) . . ?
C66A C65A H65A 119.8 . . ?
C64A C65A H65A 119.8 . . ?
C66B C65B C64B 120.66(13) . . ?
C66B C65B H65B 119.7 . . ?
C64B C65B H65B 119.7 . . ?
C66C C65C C64C 120.68(13) . . ?
C66C C65C H65C 119.7 . . ?
C64C C65C H65C 119.7 . . ?
C66D C65D C64D 120.40(13) . . ?
C66D C65D H65D 119.8 . . ?
C64D C65D H65D 119.8 . . ?
C65A C66A C61A 119.88(13) . . ?
C65A C66A H66A 120.1 . . ?
C61A C66A H66A 120.1 . . ?
C65B C66B C61B 119.87(13) . . ?
C65B C66B H66B 120.1 . . ?
C61B C66B H66B 120.1 . . ?
C65C C66C C61C 120.00(13) . . ?
C65C C66C H66C 120.0 . . ?
C61C C66C H66C 120.0 . . ?
C65D C66D C61D 120.01(13) . . ?
C65D C66D H66D 120.0 . . ?
C61D C66D H66D 120.0 . . ?
O4A C67A H67A 109.5 . . ?
O4A C67A H67B 109.5 . . ?
H67A C67A H67B 109.5 . . ?
O4A C67A H67C 109.5 . . ?
H67A C67A H67C 109.5 . . ?
H67B C67A H67C 109.5 . . ?
O4B C67B H67D 109.5 . . ?
O4B C67B H67E 109.5 . . ?
H67D C67B H67E 109.5 . . ?
O4B C67B H67F 109.5 . . ?
H67D C67B H67F 109.5 . . ?
H67E C67B H67F 109.5 . . ?
O4C C67C H67G 109.5 . . ?
O4C C67C H67H 109.5 . . ?
H67G C67C H67H 109.5 . . ?
O4C C67C H67I 109.5 . . ?
H67G C67C H67I 109.5 . . ?
H67H C67C H67I 109.5 . . ?
O4D C67D H67J 109.5 . . ?
O4D C67D H67K 109.5 . . ?
H67J C67D H67K 109.5 . . ?
O4D C67D H67L 109.5 . . ?
H67J C67D H67L 109.5 . . ?
H67K C67D H67L 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
C6A N1A C2A N2A 177.40(12) . . . . ?
C6A N1A C2A N3A -1.7(2) . . . . ?
C4A N3A C2A N2A -175.53(12) . . . . ?
C4A N3A C2A N1A 3.6(2) . . . . ?
C6B N1B C2B N2B 178.80(12) . . . . ?
C6B N1B C2B N3B -1.67(19) . . . . ?
C4B N3B C2B N2B 179.99(11) . . . . ?
C4B N3B C2B N1B 0.46(18) . . . . ?
C6C N1C C2C N2C 178.64(12) . . . . ?
C6C N1C C2C N3C -1.27(19) . . . . ?
C4C N3C C2C N2C -178.15(12) . . . . ?
C4C N3C C2C N1C 1.76(19) . . . . ?
C6D N1D C2D N2D 178.87(12) . . . . ?
C6D N1D C2D N3D 0.73(19) . . . . ?
C4D N3D C2D N2D -179.65(11) . . . . ?
C4D N3D C2D N1D -1.50(19) . . . . ?
C2A N3A C4A N5A -2.39(19) . . . . ?
C2A N3A C4A C41A 177.31(11) . . . . ?
C6A N5A C4A N3A -0.5(2) . . . . ?
C6A N5A C4A C41A 179.80(11) . . . . ?
C2B N3B C4B N5B 1.41(19) . . . . ?
C2B N3B C4B C41B -178.62(11) . . . . ?
C6B N5B C4B N3B -1.75(19) . . . . ?
C6B N5B C4B C41B 178.28(11) . . . . ?
C2C N3C C4C N5C -1.24(19) . . . . ?
C2C N3C C4C C41C 177.59(11) . . . . ?
C6C N5C C4C N3C 0.30(19) . . . . ?
C6C N5C C4C C41C -178.54(11) . . . . ?
C6D N5D C4D N3D 0.71(19) . . . . ?
C6D N5D C4D C41D -175.92(11) . . . . ?
C2D N3D C4D N5D 0.72(19) . . . . ?
C2D N3D C4D C41D 177.29(11) . . . . ?
C2A N1A C6A N5A -1.7(2) . . . . ?
C2A N1A C6A N6A 178.68(12) . . . . ?
C4A N5A C6A N1A 2.7(2) . . . . ?
C4A N5A C6A N6A -177.65(12) . . . . ?
C61A N6A C6A N1A -179.25(12) . . . . ?
C61A N6A C6A N5A 1.1(2) . . . . ?
C2B N1B C6B N5B 1.26(19) . . . . ?
C2B N1B C6B N6B -179.16(12) . . . . ?
C4B N5B C6B N1B 0.28(19) . . . . ?
C4B N5B C6B N6B -179.29(12) . . . . ?
C61B N6B C6B N1B -174.04(12) . . . . ?
C61B N6B C6B N5B 5.6(2) . . . . ?
C4C N5C C6C N1C 0.29(19) . . . . ?
C4C N5C C6C N6C 179.06(12) . . . . ?
C2C N1C C6C N5C 0.16(19) . . . . ?
C2C N1C C6C N6C -178.62(12) . . . . ?
C61C N6C C6C N5C -4.73(19) . . . . ?
C61C N6C C6C N1C 174.15(12) . . . . ?
C2D N1D C6D N6D -177.05(12) . . . . ?
C2D N1D C6D N5D 0.96(19) . . . . ?
C61D N6D C6D N1D 177.76(12) . . . . ?
C61D N6D C6D N5D -0.42(19) . . . . ?
C4D N5D C6D N1D -1.62(19) . . . . ?
C4D N5D C6D N6D 176.38(11) . . . . ?
N3A C4A C41A C46A 10.24(18) . . . . ?
N5A C4A C41A C46A -170.02(12) . . . . ?
N3A C4A C41A C42A -169.66(12) . . . . ?
N5A C4A C41A C42A 10.08(18) . . . . ?
N3B C4B C41B C46B 1.57(17) . . . . ?
N5B C4B C41B C46B -178.46(11) . . . . ?
N3B C4B C41B C42B 179.63(11) . . . . ?
N5B C4B C41B C42B -0.40(18) . . . . ?
N3C C4C C41C C42C 168.80(12) . . . . ?
N5C C4C C41C C42C -12.25(18) . . . . ?
N3C C4C C41C C46C -12.29(18) . . . . ?
N5C C4C C41C C46C 166.66(12) . . . . ?
N5D C4D C41D C46D 176.49(12) . . . . ?
N3D C4D C41D C46D -0.44(18) . . . . ?
N5D C4D C41D C42D 0.84(18) . . . . ?
N3D C4D C41D C42D -176.09(12) . . . . ?
C46A C41A C42A C43A -0.46(19) . . . . ?
C4A C41A C42A C43A 179.44(12) . . . . ?
C46B C41B C42B C43B -0.13(19) . . . . ?
C4B C41B C42B C43B -178.17(12) . . . . ?
C46C C41C C42C C43C 0.21(19) . . . . ?
C4C C41C C42C C43C 179.11(12) . . . . ?
C46D C41D C42D C43D -1.3(2) . . . . ?
C4D C41D C42D C43D 174.33(12) . . . . ?
C47A O1A C43A C42A -6.18(18) . . . . ?
C47A O1A C43A C44A 172.71(12) . . . . ?
C41A C42A C43A O1A 179.89(12) . . . . ?
C41A C42A C43A C44A 1.06(19) . . . . ?
C47B O1B C43B C42B -5.9(2) . . . . ?
C47B O1B C43B C44B 174.52(14) . . . . ?
C41B C42B C43B O1B 179.54(12) . . . . ?
C41B C42B C43B C44B -0.9(2) . . . . ?
C47C O1C C43C C42C -8.87(19) . . . . ?
C47C O1C C43C C44C 172.22(12) . . . . ?
C41C C42C C43C O1C -179.38(12) . . . . ?
C41C C42C C43C C44C -0.53(19) . . . . ?
C47D O1D C43D C42D 6.2(2) . . . . ?
C47D O1D C43D C44D -171.53(15) . . . . ?
C41D C42D C43D O1D -178.50(13) . . . . ?
C41D C42D C43D C44D -0.9(2) . . . . ?
C48A O2A C44A C45A -74.04(16) . . . . ?
C48A O2A C44A C43A 109.01(14) . . . . ?
O1A C43A C44A O2A -2.54(17) . . . . ?
C42A C43A C44A O2A 176.39(11) . . . . ?
O1A C43A C44A C45A -179.57(11) . . . . ?
C42A C43A C44A C45A -0.64(19) . . . . ?
C48B O2B C44B C45B -71.18(16) . . . . ?
C48B O2B C44B C43B 111.77(14) . . . . ?
O1B C43B C44B O2B -1.76(18) . . . . ?
C42B C43B C44B O2B 178.63(12) . . . . ?
O1B C43B C44B C45B -178.89(12) . . . . ?
C42B C43B C44B C45B 1.5(2) . . . . ?
C48C O2C C44C C45C -83.01(15) . . . . ?
C48C O2C C44C C43C 96.74(14) . . . . ?
O1C C43C C44C O2C -0.26(17) . . . . ?
C42C C43C C44C O2C -179.23(12) . . . . ?
O1C C43C C44C C45C 179.50(12) . . . . ?
C42C C43C C44C C45C 0.53(19) . . . . ?
C48D O2D C44D C45D -89.39(15) . . . . ?
C48D O2D C44D C43D 87.90(15) . . . . ?
O1D C43D C44D O2D 1.44(18) . . . . ?
C42D C43D C44D O2D -176.44(12) . . . . ?
O1D C43D C44D C45D 178.76(12) . . . . ?
C42D C43D C44D C45D 0.9(2) . . . . ?
C49A O3A C45A C46A 1.73(19) . . . . ?
C49A O3A C45A C44A -177.94(12) . . . . ?
O2A C44A C45A O3A 2.33(18) . . . . ?
C43A C44A C45A O3A 179.26(12) . . . . ?
O2A C44A C45A C46A -177.35(12) . . . . ?
C43A C44A C45A C46A -0.41(19) . . . . ?
C49B O3B C45B C46B 0.66(19) . . . . ?
C49B O3B C45B C44B -178.52(12) . . . . ?
O2B C44B C45B O3B 1.09(18) . . . . ?
C43B C44B C45B O3B 178.13(12) . . . . ?
O2B C44B C45B C46B -178.12(12) . . . . ?
C43B C44B C45B C46B -1.1(2) . . . . ?
C49C O3C C45C C46C 9.3(2) . . . . ?
C49C O3C C45C C44C -171.61(12) . . . . ?
O2C C44C C45C O3C 0.41(18) . . . . ?
C43C C44C C45C O3C -179.34(12) . . . . ?
O2C C44C C45C C46C 179.54(12) . . . . ?
C43C C44C C45C C46C -0.22(19) . . . . ?
C49D O3D C45D C46D -4.0(2) . . . . ?
C49D O3D C45D C44D 172.79(13) . . . . ?
O2D C44D C45D O3D 1.67(19) . . . . ?
C43D C44D C45D O3D -175.63(12) . . . . ?
O2D C44D C45D C46D 178.57(13) . . . . ?
C43D C44D C45D C46D 1.3(2) . . . . ?
O3A C45A C46A C41A -178.63(12) . . . . ?
C44A C45A C46A C41A 1.0(2) . . . . ?
C42A C41A C46A C45A -0.6(2) . . . . ?
C4A C41A C46A C45A 179.53(12) . . . . ?
O3B C45B C46B C41B -179.07(12) . . . . ?
C44B C45B C46B C41B 0.1(2) . . . . ?
C42B C41B C46B C45B 0.54(19) . . . . ?
C4B C41B C46B C45B 178.60(12) . . . . ?
O3C C45C C46C C41C 178.93(12) . . . . ?
C44C C45C C46C C41C -0.1(2) . . . . ?
C42C C41C C46C C45C 0.1(2) . . . . ?
C4C C41C C46C C45C -178.80(12) . . . . ?
O3D C45D C46D C41D 173.18(13) . . . . ?
C44D C45D C46D C41D -3.4(2) . . . . ?
C42D C41D C46D C45D 3.4(2) . . . . ?
C4D C41D C46D C45D -172.18(12) . . . . ?
C6A N6A C61A C62A 129.82(14) . . . . ?
C6A N6A C61A C66A -51.72(19) . . . . ?
C6B N6B C61B C62B 125.02(14) . . . . ?
C6B N6B C61B C66B -57.51(19) . . . . ?
C6C N6C C61C C62C -120.00(14) . . . . ?
C6C N6C C61C C66C 61.90(18) . . . . ?
C6D N6D C61D C62D -114.95(15) . . . . ?
C6D N6D C61D C66D 66.62(17) . . . . ?
C66A C61A C62A C63A -1.41(19) . . . . ?
N6A C61A C62A C63A 177.07(12) . . . . ?
C66B C61B C62B C63B 0.83(19) . . . . ?
N6B C61B C62B C63B 178.40(12) . . . . ?
C66C C61C C62C C63C 1.04(19) . . . . ?
N6C C61C C62C C63C -177.09(12) . . . . ?
C66D C61D C62D C63D 1.3(2) . . . . ?
N6D C61D C62D C63D -177.14(12) . . . . ?
C61A C62A C63A C64A 1.25(19) . . . . ?
C61B C62B C63B C64B 0.9(2) . . . . ?
C61C C62C C63C C64C -0.1(2) . . . . ?
C61D C62D C63D C64D 1.0(2) . . . . ?
C67A O4A C64A C63A -0.47(18) . . . . ?
C67A O4A C64A C65A -179.41(12) . . . . ?
C62A C63A C64A O4A -178.79(12) . . . . ?
C62A C63A C64A C65A 0.11(19) . . . . ?
C67B O4B C64B C63B -1.85(18) . . . . ?
C67B O4B C64B C65B 178.92(11) . . . . ?
C62B C63B C64B O4B 179.16(12) . . . . ?
C62B C63B C64B C65B -1.62(19) . . . . ?
C67C O4C C64C C63C -3.08(18) . . . . ?
C67C O4C C64C C65C 176.41(11) . . . . ?
C62C C63C C64C O4C 178.43(12) . . . . ?
C62C C63C C64C C65C -1.05(19) . . . . ?
C67D O4D C64D C63D 3.5(2) . . . . ?
C67D O4D C64D C65D -177.74(14) . . . . ?
C62D C63D C64D O4D 176.04(13) . . . . ?
C62D C63D C64D C65D -2.7(2) . . . . ?
O4A C64A C65A C66A 177.69(12) . . . . ?
C63A C64A C65A C66A -1.3(2) . . . . ?
O4B C64B C65B C66B 179.95(12) . . . . ?
C63B C64B C65B C66B 0.7(2) . . . . ?
O4C C64C C65C C66C -178.33(12) . . . . ?
C63C C64C C65C C66C 1.19(19) . . . . ?
O4D C64D C65D C66D -176.72(12) . . . . ?
C63D C64D C65D C66D 2.2(2) . . . . ?
C64A C65A C66A C61A 1.1(2) . . . . ?
C62A C61A C66A C65A 0.20(19) . . . . ?
N6A C61A C66A C65A -178.24(12) . . . . ?
C64B C65B C66B C61B 1.1(2) . . . . ?
C62B C61B C66B C65B -1.79(19) . . . . ?
N6B C61B C66B C65B -179.22(12) . . . . ?
C64C C65C C66C C61C -0.21(19) . . . . ?
C62C C61C C66C C65C -0.89(19) . . . . ?
N6C C61C C66C C65C 177.21(12) . . . . ?
C64D C65D C66D C61D 0.16(19) . . . . ?
C62D C61D C66D C65D -1.88(19) . . . . ?
N6D C61D C66D C65D 176.55(12) . . . . ?

_refine_diff_density_max         0.350
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.044



####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2215945'
loop_
_audit_author_name
_audit_author_address
'Edward R.T. Tiekink'
;Sunway University
Malaysia
;
_audit_update_record             
;
2022-10-28 deposited with the CCDC.	2022-12-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H21 N5 O4'
_chemical_formula_sum            'C19 H21 N5 O4'
_chemical_formula_weight         383.41

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                   7.85094(7)
_cell_length_b                   17.15939(18)
_cell_length_c                   14.25371(12)
_cell_angle_alpha                90
_cell_angle_beta                 101.5857(8)
_cell_angle_gamma                90
_cell_volume                     1881.10(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    16291
_cell_measurement_theta_min      4.0320
_cell_measurement_theta_max      76.7590

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.184
_exptl_crystal_size_mid          0.093
_exptl_crystal_size_min          0.071
_exptl_absorpt_coefficient_mu    0.809
_shelx_estimated_absorpt_T_min   0.865
_shelx_estimated_absorpt_T_max   0.945
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.699
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'CrysAlisPro (Rigaku OD, 2017)'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.2558
_diffrn_reflns_number            25531
_diffrn_reflns_av_unetI/netI     0.0128
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         4.082
_diffrn_reflns_theta_max         75.275
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3884
_reflns_number_gt                3661
_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 (Rigaku OD, 2017)'
_computing_cell_refinement       'CrysAlisPro (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro (Rigaku OD, 2017)'
_computing_structure_solution    'SHELXS (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 2012), DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_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)+(0.0558P)²+0.5212P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3884
_refine_ls_number_parameters     266
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0976
_refine_ls_wR_factor_gt          0.0960
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.047
_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 0.87547(9) 0.23435(4) 0.75822(5) 0.02335(18) Uani 1 1 d . . . . .
O2 O 1.15400(9) 0.31910(4) 0.82779(5) 0.02260(17) Uani 1 1 d . . . . .
O3 O 1.16165(9) 0.47459(5) 0.79458(6) 0.02612(19) Uani 1 1 d . . . . .
O4 O 0.10186(11) 0.08373(5) 0.49425(6) 0.03008(19) Uani 1 1 d . . . . .
N1 N 0.23396(10) 0.53058(5) 0.55623(6) 0.01851(18) Uani 1 1 d . . . . .
H1N H 0.2458(12) 0.6690(7) 0.5844(9) 0.022 Uiso 1 1 d D U . . .
H2N H 0.4290(14) 0.6785(7) 0.6443(8) 0.022 Uiso 1 1 d D U . . .
N2 N 0.34864(11) 0.64963(5) 0.60930(7) 0.02243(19) Uani 1 1 d D . . . .
N3 N 0.52948(10) 0.54394(5) 0.64169(6) 0.01917(18) Uani 1 1 d . . . . .
N5 N 0.41706(10) 0.41858(5) 0.59088(6) 0.01823(18) Uani 1 1 d . . . . .
N6 N 0.13051(11) 0.40815(5) 0.51169(6) 0.01995(19) Uani 1 1 d D . . . .
H3N H 0.0273(12) 0.4298(7) 0.4943(9) 0.024 Uiso 1 1 d D U . . .
C2 C 0.37078(12) 0.57275(6) 0.60152(7) 0.0181(2) Uani 1 1 d . . . . .
C4 C 0.54167(12) 0.46688(6) 0.63410(7) 0.0174(2) Uani 1 1 d . . . . .
C6 C 0.26546(12) 0.45351(6) 0.55377(7) 0.0174(2) Uani 1 1 d . . . . .
C41 C 0.70777(12) 0.42915(6) 0.68066(7) 0.0183(2) Uani 1 1 d . . . . .
C42 C 0.70840(12) 0.34890(6) 0.69519(7) 0.0194(2) Uani 1 1 d . . . . .
H42 H 0.606225 0.319103 0.673125 0.023 Uiso 1 1 calc R U . . .
C43 C 0.86001(12) 0.31289(6) 0.74230(7) 0.0195(2) Uani 1 1 d . . . . .
C44 C 1.01066(12) 0.35646(6) 0.77587(7) 0.0201(2) Uani 1 1 d . . . . .
C45 C 1.00880(12) 0.43694(6) 0.75993(7) 0.0204(2) Uani 1 1 d . . . . .
C46 C 0.85748(12) 0.47340(6) 0.71185(7) 0.0200(2) Uani 1 1 d . . . . .
H46 H 0.856379 0.527960 0.700427 0.024 Uiso 1 1 calc R U . . .
C47 C 0.72509(13) 0.18755(6) 0.72366(8) 0.0270(2) Uani 1 1 d . . . . .
H47A H 0.686327 0.195750 0.654630 0.040 Uiso 1 1 calc R U . . .
H47B H 0.631822 0.202374 0.756662 0.040 Uiso 1 1 calc R U . . .
H47C H 0.754129 0.132461 0.736036 0.040 Uiso 1 1 calc R U . . .
C48 C 1.29609(14) 0.31130(8) 0.77882(8) 0.0323(3) Uani 1 1 d . . . . .
H48A H 1.257131 0.282577 0.718925 0.049 Uiso 1 1 calc R U . . .
H48B H 1.391363 0.282861 0.819562 0.049 Uiso 1 1 calc R U . . .
H48C H 1.336728 0.363135 0.764552 0.049 Uiso 1 1 calc R U . . .
C49 C 1.16107(13) 0.55744(7) 0.78791(8) 0.0264(2) Uani 1 1 d . . . . .
H49A H 1.122826 0.573009 0.720827 0.040 Uiso 1 1 calc R U . . .
H49B H 1.278661 0.577312 0.812284 0.040 Uiso 1 1 calc R U . . .
H49C H 1.081332 0.578992 0.826020 0.040 Uiso 1 1 calc R U . . .
C61 C 0.13384(12) 0.32548(6) 0.50822(7) 0.0181(2) Uani 1 1 d . . . . .
C62 C 0.00017(12) 0.28427(6) 0.53721(7) 0.0204(2) Uani 1 1 d . . . . .
H62 H -0.086930 0.311688 0.561384 0.025 Uiso 1 1 calc R U . . .
C63 C -0.00669(13) 0.20381(6) 0.53106(7) 0.0233(2) Uani 1 1 d . . . . .
H63 H -0.099487 0.176403 0.549892 0.028 Uiso 1 1 calc R U . . .
C64 C 0.12187(14) 0.16291(6) 0.49739(7) 0.0226(2) Uani 1 1 d . . . . .
C65 C 0.25772(14) 0.20346(6) 0.47027(8) 0.0238(2) Uani 1 1 d . . . . .
H65 H 0.347313 0.175851 0.448551 0.029 Uiso 1 1 calc R U . . .
C66 C 0.26234(13) 0.28455(6) 0.47499(7) 0.0224(2) Uani 1 1 d . . . . .
H66 H 0.354158 0.312063 0.455303 0.027 Uiso 1 1 calc R U . . .
C67 C 0.22021(19) 0.03928(7) 0.45250(10) 0.0393(3) Uani 1 1 d . . . . .
H67A H 0.215434 0.056874 0.386617 0.059 Uiso 1 1 calc R U . . .
H67B H 0.188413 -0.015961 0.452220 0.059 Uiso 1 1 calc R U . . .
H67C H 0.338363 0.046280 0.489900 0.059 Uiso 1 1 calc R U . . .


_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 C43 1.3680(12) . ?
O1 C47 1.4311(12) . ?
O2 C44 1.3750(11) . ?
O2 C48 1.4360(13) . ?
O3 C45 1.3650(12) . ?
O3 C49 1.4249(13) . ?
O4 C64 1.3673(13) . ?
O4 C67 1.4218(15) . ?
N1 C6 1.3472(13) . ?
N1 C2 1.3474(12) . ?
N2 C2 1.3382(13) . ?
N2 H1N 0.879(8) . ?
N2 H2N 0.876(8) . ?
N3 C4 1.3316(13) . ?
N3 C2 1.3557(12) . ?
N5 C4 1.3347(12) . ?
N5 C6 1.3427(12) . ?
N6 C6 1.3538(12) . ?
N6 C61 1.4198(12) . ?
N6 H3N 0.880(8) . ?
C4 C41 1.4875(13) . ?
C41 C42 1.3924(14) . ?
C41 C46 1.3949(13) . ?
C42 C43 1.3886(13) . ?
C42 H42 0.9500 . ?
C43 C44 1.3998(14) . ?
C44 C45 1.3991(15) . ?
C45 C46 1.3948(13) . ?
C46 H46 0.9500 . ?
C47 H47A 0.9800 . ?
C47 H47B 0.9800 . ?
C47 H47C 0.9800 . ?
C48 H48A 0.9800 . ?
C48 H48B 0.9800 . ?
C48 H48C 0.9800 . ?
C49 H49A 0.9800 . ?
C49 H49B 0.9800 . ?
C49 H49C 0.9800 . ?
C61 C66 1.3882(14) . ?
C61 C62 1.3951(14) . ?
C62 C63 1.3837(15) . ?
C62 H62 0.9500 . ?
C63 C64 1.3915(15) . ?
C63 H63 0.9500 . ?
C64 C65 1.3917(15) . ?
C65 C66 1.3932(15) . ?
C65 H65 0.9500 . ?
C66 H66 0.9500 . ?
C67 H67A 0.9800 . ?
C67 H67B 0.9800 . ?
C67 H67C 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
C43 O1 C47 117.14(7) . . ?
C44 O2 C48 114.43(8) . . ?
C45 O3 C49 117.21(8) . . ?
C64 O4 C67 117.80(9) . . ?
C6 N1 C2 114.00(8) . . ?
C2 N2 H1N 117.6(8) . . ?
C2 N2 H2N 121.0(8) . . ?
H1N N2 H2N 120.9(12) . . ?
C4 N3 C2 113.75(8) . . ?
C4 N5 C6 114.46(8) . . ?
C6 N6 C61 124.86(8) . . ?
C6 N6 H3N 118.4(9) . . ?
C61 N6 H3N 115.7(9) . . ?
N2 C2 N1 117.69(8) . . ?
N2 C2 N3 116.63(8) . . ?
N1 C2 N3 125.67(9) . . ?
N3 C4 N5 126.60(9) . . ?
N3 C4 C41 117.83(8) . . ?
N5 C4 C41 115.54(9) . . ?
N5 C6 N1 125.51(9) . . ?
N5 C6 N6 118.09(9) . . ?
N1 C6 N6 116.39(8) . . ?
C42 C41 C46 120.89(9) . . ?
C42 C41 C4 118.26(8) . . ?
C46 C41 C4 120.82(9) . . ?
C43 C42 C41 119.28(9) . . ?
C43 C42 H42 120.4 . . ?
C41 C42 H42 120.4 . . ?
O1 C43 C42 123.88(9) . . ?
O1 C43 C44 115.39(8) . . ?
C42 C43 C44 120.73(9) . . ?
O2 C44 C43 118.62(9) . . ?
O2 C44 C45 121.89(9) . . ?
C43 C44 C45 119.41(9) . . ?
O3 C45 C46 124.45(10) . . ?
O3 C45 C44 115.38(8) . . ?
C46 C45 C44 120.17(9) . . ?
C45 C46 C41 119.50(10) . . ?
C45 C46 H46 120.3 . . ?
C41 C46 H46 120.3 . . ?
O1 C47 H47A 109.5 . . ?
O1 C47 H47B 109.5 . . ?
H47A C47 H47B 109.5 . . ?
O1 C47 H47C 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
O2 C48 H48A 109.5 . . ?
O2 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
O2 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
O3 C49 H49A 109.5 . . ?
O3 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
O3 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
C66 C61 C62 119.08(10) . . ?
C66 C61 N6 122.48(9) . . ?
C62 C61 N6 118.42(9) . . ?
C63 C62 C61 120.60(9) . . ?
C63 C62 H62 119.7 . . ?
C61 C62 H62 119.7 . . ?
C62 C63 C64 120.22(9) . . ?
C62 C63 H63 119.9 . . ?
C64 C63 H63 119.9 . . ?
O4 C64 C63 115.21(9) . . ?
O4 C64 C65 125.25(10) . . ?
C63 C64 C65 119.54(10) . . ?
C64 C65 C66 120.00(9) . . ?
C64 C65 H65 120.0 . . ?
C66 C65 H65 120.0 . . ?
C61 C66 C65 120.54(9) . . ?
C61 C66 H66 119.7 . . ?
C65 C66 H66 119.7 . . ?
O4 C67 H67A 109.5 . . ?
O4 C67 H67B 109.5 . . ?
H67A C67 H67B 109.5 . . ?
O4 C67 H67C 109.5 . . ?
H67A C67 H67C 109.5 . . ?
H67B C67 H67C 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
C6 N1 C2 N2 -178.25(9) . . . . ?
C6 N1 C2 N3 0.58(14) . . . . ?
C4 N3 C2 N2 178.06(9) . . . . ?
C4 N3 C2 N1 -0.78(14) . . . . ?
C2 N3 C4 N5 1.13(14) . . . . ?
C2 N3 C4 C41 -176.70(8) . . . . ?
C6 N5 C4 N3 -1.22(14) . . . . ?
C6 N5 C4 C41 176.66(8) . . . . ?
C4 N5 C6 N1 0.96(14) . . . . ?
C4 N5 C6 N6 -177.69(8) . . . . ?
C2 N1 C6 N5 -0.68(13) . . . . ?
C2 N1 C6 N6 177.99(8) . . . . ?
C61 N6 C6 N5 3.62(14) . . . . ?
C61 N6 C6 N1 -175.16(9) . . . . ?
N3 C4 C41 C42 163.54(9) . . . . ?
N5 C4 C41 C42 -14.54(13) . . . . ?
N3 C4 C41 C46 -14.32(13) . . . . ?
N5 C4 C41 C46 167.61(9) . . . . ?
C46 C41 C42 C43 0.67(14) . . . . ?
C4 C41 C42 C43 -177.18(9) . . . . ?
C47 O1 C43 C42 0.05(14) . . . . ?
C47 O1 C43 C44 -179.05(9) . . . . ?
C41 C42 C43 O1 -178.43(9) . . . . ?
C41 C42 C43 C44 0.62(15) . . . . ?
C48 O2 C44 C43 109.86(11) . . . . ?
C48 O2 C44 C45 -73.33(13) . . . . ?
O1 C43 C44 O2 -5.25(13) . . . . ?
C42 C43 C44 O2 175.61(8) . . . . ?
O1 C43 C44 C45 177.85(9) . . . . ?
C42 C43 C44 C45 -1.28(15) . . . . ?
C49 O3 C45 C46 5.48(14) . . . . ?
C49 O3 C45 C44 -174.27(9) . . . . ?
O2 C44 C45 O3 3.63(14) . . . . ?
C43 C44 C45 O3 -179.58(9) . . . . ?
O2 C44 C45 C46 -176.14(9) . . . . ?
C43 C44 C45 C46 0.65(14) . . . . ?
O3 C45 C46 C41 -179.13(9) . . . . ?
C44 C45 C46 C41 0.62(15) . . . . ?
C42 C41 C46 C45 -1.29(14) . . . . ?
C4 C41 C46 C45 176.51(9) . . . . ?
C6 N6 C61 C66 -52.37(14) . . . . ?
C6 N6 C61 C62 129.24(10) . . . . ?
C66 C61 C62 C63 -1.39(14) . . . . ?
N6 C61 C62 C63 177.06(9) . . . . ?
C61 C62 C63 C64 1.16(14) . . . . ?
C67 O4 C64 C63 174.47(10) . . . . ?
C67 O4 C64 C65 -5.69(15) . . . . ?
C62 C63 C64 O4 -179.92(9) . . . . ?
C62 C63 C64 C65 0.24(15) . . . . ?
O4 C64 C65 C66 178.78(10) . . . . ?
C63 C64 C65 C66 -1.38(15) . . . . ?
C62 C61 C66 C65 0.23(14) . . . . ?
N6 C61 C66 C65 -178.15(9) . . . . ?
C64 C65 C66 C61 1.15(15) . . . . ?

_refine_diff_density_max         0.234
_refine_diff_density_min         -0.245
_refine_diff_density_rms         0.045



