# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

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

data_RP0003_a
_database_code_depnum_ccdc_archive 'CCDC 1863406'
_audit_update_record             
;
2018-08-22 deposited with the CCDC.	2019-05-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H13 N3 O3'
_chemical_formula_weight         271.27

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                   13.956(9)
_cell_length_b                   15.246(7)
_cell_length_c                   15.246(7)
_cell_angle_alpha                77.91
_cell_angle_beta                 62.76
_cell_angle_gamma                62.76
_cell_volume                     2564(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3844
_cell_measurement_theta_min      2.79
_cell_measurement_theta_max      23.25

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_F_000             1136.0
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.102
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            33720
_diffrn_reflns_av_unetI/netI     0.2692
_diffrn_reflns_av_R_equivalents  0.0645
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.502
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             7617
_reflns_number_gt                2718
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0902P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.006(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7516
_refine_ls_number_parameters     730
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1780
_refine_ls_R_factor_gt           0.1076
_refine_ls_wR_factor_ref         0.3265
_refine_ls_wR_factor_gt          0.2497
_refine_ls_goodness_of_fit_ref   0.915
_refine_ls_restrained_S_all      0.915
_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
O6 O 0.2273(4) 0.5962(3) 0.6339(3) 0.0877(15) Uani 1 1 d . . . . .
O8 O 0.0310(3) 0.8719(3) 0.8988(3) 0.0926(15) Uani 1 1 d . . . . .
H8 H 0.099251 0.835403 0.891526 0.139 Uiso 1 1 calc R U . . .
O12 O 0.8606(4) 0.8657(3) 0.5963(3) 0.0917(15) Uani 1 1 d . . . . .
O9 O 0.4573(3) 0.9038(3) 0.8648(3) 0.0893(14) Uani 1 1 d . . . . .
O10 O 0.4029(3) 0.8992(4) 0.6287(3) 0.0916(15) Uani 1 1 d . . . . .
H10 H 0.430889 0.905498 0.662800 0.137 Uiso 1 1 calc R U . . .
O7 O 0.3230(3) 0.6346(3) 0.9043(3) 0.0899(15) Uani 1 1 d . . . . .
O5 O -0.0703(4) 0.6010(3) 0.8712(3) 0.0880(14) Uani 1 1 d . . . . .
H5 H -0.010543 0.609925 0.834172 0.132 Uiso 1 1 calc R U . . .
O4 O 0.4907(4) 0.8769(3) 0.2942(3) 0.0966(15) Uani 1 1 d . . . . .
O11 O 0.8040(4) 0.6291(3) 0.6026(3) 0.0922(15) Uani 1 1 d . . . . .
H11 H 0.775859 0.632725 0.564456 0.138 Uiso 1 1 calc R U . . .
O2 O -0.2147(4) 1.2055(3) 0.8764(3) 0.1026(16) Uani 1 1 d . . . . .
O1 O -0.3394(4) 0.6241(3) 1.2052(3) 0.0973(16) Uani 1 1 d . . . . .
O3 O 0.8661(4) 0.2948(3) 0.6240(3) 0.1001(16) Uani 1 1 d . . . . .
N11 N 0.9957(4) 0.7295(4) 0.6331(3) 0.0754(15) Uani 1 1 d . . . . .
H11A H 1.055758 0.704541 0.647582 0.091 Uiso 1 1 calc R U . . .
N10 N 0.9494(4) 0.6698(4) 0.6269(3) 0.0791(16) Uani 1 1 d . . . . .
N5 N 0.3583(4) 0.7714(4) 0.8666(3) 0.0781(15) Uani 1 1 d . . . . .
H5A H 0.408061 0.796040 0.852570 0.094 Uiso 1 1 calc R U . . .
N4 N 0.2465(4) 0.8307(4) 0.8727(3) 0.0778(16) Uani 1 1 d . . . . .
N6 N 0.5738(4) 0.6692(4) 0.8600(4) 0.0848(17) Uani 1 1 d . . . . .
N8 N 0.6287(4) 0.8675(3) 0.7281(4) 0.0779(15) Uani 1 1 d . . . . .
H8A H 0.702747 0.855208 0.702677 0.093 Uiso 1 1 calc R U . . .
N3 N 0.4331(4) 0.6401(4) 0.6690(4) 0.0819(17) Uani 1 1 d . . . . .
N7 N 0.5772(4) 0.8719(3) 0.6700(4) 0.0741(15) Uani 1 1 d . . . . .
N1 N 0.1186(4) 0.6275(3) 0.8300(4) 0.0783(16) Uani 1 1 d . . . . .
N12 N 1.1036(5) 0.8314(4) 0.6387(4) 0.0844(17) Uani 1 1 d . . . . .
N2 N 0.2262(4) 0.6334(3) 0.7713(3) 0.0783(16) Uani 1 1 d . . . . .
H2 H 0.262613 0.646647 0.795866 0.094 Uiso 1 1 calc R U . . .
N9 N 0.7430(5) 0.8601(4) 0.8304(4) 0.0848(17) Uani 1 1 d . . . . .
C52 C 1.0053(5) 0.8821(5) 0.6257(4) 0.0733(19) Uani 1 1 d . . . . .
C47 C 0.8681(5) 0.5342(5) 0.6164(4) 0.0693(18) Uani 1 1 d . . . . .
C00R C 1.0059(5) 0.5771(5) 0.6401(4) 0.0747(19) Uani 1 1 d . . . . .
H00R H 1.071795 0.555352 0.653637 0.090 Uiso 1 1 calc R U . . .
C51 C 0.9474(5) 0.8262(5) 0.6166(4) 0.074(2) Uani 1 1 d . . . . .
C24 C 0.5131(5) 0.6177(4) 0.8749(4) 0.0679(17) Uani 1 1 d . . . . .
C18 C 0.0178(5) 0.9660(5) 0.8855(4) 0.0730(18) Uani 1 1 d . . . . .
C34 C 0.4834(5) 0.8854(4) 0.5334(4) 0.0677(17) Uani 1 1 d . . . . .
C19 C 0.1078(5) 0.9919(4) 0.8657(4) 0.0728(19) Uani 1 1 d . . . . .
C46 C 0.8327(5) 0.4648(5) 0.6112(4) 0.0747(19) Uani 1 1 d . . . . .
H46 H 0.767311 0.484420 0.597490 0.090 Uiso 1 1 calc R U . . .
C48 C 0.9659(5) 0.5072(4) 0.6337(4) 0.0707(18) Uani 1 1 d . . . . .
C10 C 0.3875(5) 0.6248(4) 0.6180(5) 0.0712(18) Uani 1 1 d . . . . .
C6 C -0.0267(5) 0.6342(4) 0.9924(4) 0.0708(17) Uani 1 1 d . . . . .
C45 C 0.8937(6) 0.3685(5) 0.6261(4) 0.078(2) Uani 1 1 d . . . . .
C7 C -0.0966(5) 0.6153(4) 0.9654(4) 0.0704(18) Uani 1 1 d . . . . .
C2 C -0.2028(5) 0.6104(4) 1.0358(4) 0.0733(19) Uani 1 1 d . . . . .
H2A H -0.249202 0.596177 1.017423 0.088 Uiso 1 1 calc R U . . .
C28 C 0.6832(5) 0.6208(5) 0.8546(4) 0.083(2) Uani 1 1 d . . . . .
H28 H 0.725810 0.656444 0.846387 0.099 Uiso 1 1 calc R U . . .
C9 C 0.2705(5) 0.6174(4) 0.6746(5) 0.0746(19) Uani 1 1 d . . . . .
C16 C -0.1103(6) 1.1324(5) 0.8741(4) 0.083(2) Uani 1 1 d . . . . .
C37 C 0.5636(5) 0.8826(4) 0.8267(5) 0.0741(19) Uani 1 1 d . . . . .
C35 C 0.4432(5) 0.8891(4) 0.4650(4) 0.0720(18) Uani 1 1 d . . . . .
H35 H 0.364684 0.901032 0.484152 0.086 Uiso 1 1 calc R U . . .
C38 C 0.6284(5) 0.8758(4) 0.8808(5) 0.074(2) Uani 1 1 d . . . . .
C25 C 0.5604(6) 0.5165(5) 0.8813(4) 0.085(2) Uani 1 1 d . . . . .
H25 H 0.516334 0.482156 0.889517 0.102 Uiso 1 1 calc R U . . .
C33 C 0.6000(5) 0.8649(4) 0.5084(4) 0.0724(18) Uani 1 1 d . . . . .
C53 C 0.9571(5) 0.9833(5) 0.6188(4) 0.082(2) Uani 1 1 d . . . . .
H53 H 0.887237 1.017039 0.610004 0.099 Uiso 1 1 calc R U . . .
C27 C 0.7353(5) 0.5202(5) 0.8607(4) 0.0795(19) Uani 1 1 d . . . . .
H27 H 0.813003 0.488467 0.854656 0.095 Uiso 1 1 calc R U . . .
C22 C 0.2217(5) 0.9229(5) 0.8601(4) 0.082(2) Uani 1 1 d . . . . .
H22 H 0.278834 0.945150 0.847082 0.099 Uiso 1 1 calc R U . . .
C23 C 0.3894(5) 0.6741(5) 0.8826(4) 0.080(2) Uani 1 1 d . . . . .
C17 C -0.0920(5) 1.0354(5) 0.8886(4) 0.080(2) Uani 1 1 d . . . . .
H17 H -0.151277 1.016292 0.900234 0.096 Uiso 1 1 calc R U . . .
C30 C 0.5231(6) 0.8744(4) 0.3665(4) 0.076(2) Uani 1 1 d . . . . .
C26 C 0.6742(6) 0.4667(5) 0.8754(4) 0.088(2) Uani 1 1 d . . . . .
H26 H 0.707863 0.398450 0.881362 0.106 Uiso 1 1 calc R U . . .
C55 C 1.1142(6) 0.9817(5) 0.6380(4) 0.086(2) Uani 1 1 d . . . . .
H55 H 1.154436 1.014609 0.641491 0.103 Uiso 1 1 calc R U . . .
C3 C -0.2360(5) 0.6272(4) 1.1324(4) 0.076(2) Uani 1 1 d . . . . .
C50 C 0.9914(6) 0.3397(5) 0.6437(5) 0.087(2) Uani 1 1 d . . . . .
H50 H 1.034394 0.273305 0.652606 0.105 Uiso 1 1 calc R U . . .
C56 C 1.1578(5) 0.8801(5) 0.6460(5) 0.088(2) Uani 1 1 d . . . . .
H56 H 1.226400 0.845186 0.656581 0.106 Uiso 1 1 calc R U . . .
C13 C 0.5973(5) 0.6384(4) 0.5200(5) 0.081(2) Uani 1 1 d . . . . .
H13 H 0.670262 0.642169 0.488503 0.097 Uiso 1 1 calc R U . . .
C49 C 1.0258(5) 0.4078(5) 0.6482(4) 0.085(2) Uani 1 1 d . . . . .
H49 H 1.091724 0.387173 0.661443 0.102 Uiso 1 1 calc R U . . .
C39 C 0.5766(6) 0.8799(5) 0.9833(5) 0.083(2) Uani 1 1 d . . . . .
H39 H 0.499069 0.885872 1.018297 0.100 Uiso 1 1 calc R U . . .
C20 C 0.0837(6) 1.0919(5) 0.8513(4) 0.093(2) Uani 1 1 d . . . . .
H20 H 0.142563 1.111961 0.838637 0.112 Uiso 1 1 calc R U . . .
C8 C 0.0839(5) 0.6394(4) 0.9229(5) 0.084(2) Uani 1 1 d . . . . .
H8B H 0.129275 0.651183 0.944632 0.101 Uiso 1 1 calc R U . . .
C4 C -0.1678(5) 0.6446(5) 1.1610(5) 0.086(2) Uani 1 1 d . . . . .
H4 H -0.191482 0.653869 1.227383 0.103 Uiso 1 1 calc R U . . .
C42 C 0.8012(6) 0.8551(5) 0.8792(5) 0.086(2) Uani 1 1 d . . . . .
H42 H 0.879679 0.846147 0.843077 0.103 Uiso 1 1 calc R U . . .
C54 C 1.0129(6) 1.0331(5) 0.6252(4) 0.086(2) Uani 1 1 d . . . . .
H54 H 0.981964 1.101568 0.620777 0.103 Uiso 1 1 calc R U . . .
C12 C 0.5488(5) 0.6250(4) 0.4680(5) 0.086(2) Uani 1 1 d . . . . .
H12 H 0.587644 0.620138 0.399562 0.103 Uiso 1 1 calc R U . . .
C21 C -0.0229(6) 1.1607(5) 0.8552(5) 0.091(2) Uani 1 1 d . . . . .
H21 H -0.036540 1.226935 0.845030 0.110 Uiso 1 1 calc R U . . .
C14 C 0.5370(5) 0.6464(4) 0.6192(5) 0.087(2) Uani 1 1 d . . . . .
H14 H 0.570015 0.656769 0.654865 0.105 Uiso 1 1 calc R U . . .
C36 C 0.6444(6) 0.8615(4) 0.5772(5) 0.082(2) Uani 1 1 d . . . . .
H36 H 0.722815 0.851612 0.554686 0.099 Uiso 1 1 calc R U . . .
C41 C 0.7552(6) 0.8620(4) 0.9811(5) 0.084(2) Uani 1 1 d . . . . .
H41 H 0.800335 0.857934 1.012766 0.101 Uiso 1 1 calc R U . . .
C40 C 0.6392(6) 0.8752(4) 1.0320(5) 0.091(2) Uani 1 1 d . . . . .
H40 H 0.603331 0.881005 1.100376 0.109 Uiso 1 1 calc R U . . .
C32 C 0.6749(6) 0.8515(5) 0.4076(5) 0.091(2) Uani 1 1 d . . . . .
H32 H 0.753542 0.839775 0.387007 0.109 Uiso 1 1 calc R U . . .
C11 C 0.4400(5) 0.6184(4) 0.5173(4) 0.0819(19) Uani 1 1 d . . . . .
H11B H 0.404290 0.610010 0.482928 0.098 Uiso 1 1 calc R U . . .
C31 C 0.6374(6) 0.8548(5) 0.3393(5) 0.093(2) Uani 1 1 d . . . . .
H31 H 0.690467 0.843523 0.273222 0.111 Uiso 1 1 calc R U . . .
C5 C -0.0646(5) 0.6484(4) 1.0925(5) 0.085(2) Uani 1 1 d . . . . .
H5B H -0.018181 0.660672 1.112626 0.102 Uiso 1 1 calc R U . . .
C44 C 0.7656(7) 0.3194(6) 0.6062(6) 0.120(3) Uani 1 1 d . . . . .
H44A H 0.696611 0.365453 0.655277 0.180 Uiso 1 1 calc R U . . .
H44B H 0.754861 0.260791 0.609329 0.180 Uiso 1 1 calc R U . . .
H44C H 0.777215 0.348615 0.541989 0.180 Uiso 1 1 calc R U . . .
C1 C -0.4140(6) 0.6073(6) 1.1789(5) 0.118(3) Uani 1 1 d . . . . .
H1A H -0.444217 0.661408 1.139659 0.177 Uiso 1 1 calc R U . . .
H1B H -0.478831 0.601871 1.237516 0.177 Uiso 1 1 calc R U . . .
H1C H -0.369928 0.547312 1.141627 0.177 Uiso 1 1 calc R U . . .
C29 C 0.3740(6) 0.8934(6) 0.3190(5) 0.114(3) Uani 1 1 d . . . . .
H29A H 0.358302 0.839323 0.357959 0.171 Uiso 1 1 calc R U . . .
H29B H 0.363404 0.898795 0.259863 0.171 Uiso 1 1 calc R U . . .
H29C H 0.320231 0.953442 0.356198 0.171 Uiso 1 1 calc R U . . .
C15 C -0.3077(6) 1.1811(6) 0.8932(6) 0.124(3) Uani 1 1 d . . . . .
H15A H -0.280895 1.134685 0.844247 0.185 Uiso 1 1 calc R U . . .
H15B H -0.373518 1.239619 0.889347 0.185 Uiso 1 1 calc R U . . .
H15C H -0.331963 1.152256 0.957586 0.185 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
O6 C9 1.208(8) . ?
O8 C18 1.343(6) . ?
O8 H8 0.8200 . ?
O12 C51 1.234(8) . ?
O9 C37 1.222(7) . ?
O10 C34 1.355(6) . ?
O10 H10 0.8200 . ?
O7 C23 1.216(7) . ?
O5 C7 1.349(7) . ?
O5 H5 0.8200 . ?
O4 C30 1.358(8) . ?
O4 C29 1.400(8) . ?
O11 C47 1.341(7) . ?
O11 H11 0.8200 . ?
O2 C16 1.361(8) . ?
O2 C15 1.409(8) . ?
O1 C3 1.374(6) . ?
O1 C1 1.407(9) . ?
O3 C45 1.354(7) . ?
O3 C44 1.416(9) . ?
N11 C51 1.336(8) . ?
N11 N10 1.373(6) . ?
N11 H11A 0.8600 . ?
N10 C00R 1.291(7) . ?
N5 C23 1.344(7) . ?
N5 N4 1.367(7) . ?
N5 H5A 0.8600 . ?
N4 C22 1.278(7) . ?
N6 C24 1.322(7) . ?
N6 C28 1.326(8) . ?
N8 N7 1.349(7) . ?
N8 C37 1.357(7) . ?
N8 H8A 0.8600 . ?
N3 C10 1.316(8) . ?
N3 C14 1.332(7) . ?
N7 C36 1.284(7) . ?
N1 C8 1.294(8) . ?
N1 N2 1.387(6) . ?
N12 C52 1.317(8) . ?
N12 C56 1.327(8) . ?
N2 C9 1.339(8) . ?
N2 H2 0.8600 . ?
N9 C42 1.300(8) . ?
N9 C38 1.344(7) . ?
C52 C53 1.376(8) . ?
C52 C51 1.476(9) . ?
C47 C48 1.369(9) . ?
C47 C46 1.385(8) . ?
C00R C48 1.446(8) . ?
C00R H00R 0.9300 . ?
C24 C25 1.374(8) . ?
C24 C23 1.493(9) . ?
C18 C19 1.371(8) . ?
C18 C17 1.394(8) . ?
C34 C35 1.373(9) . ?
C34 C33 1.381(8) . ?
C19 C20 1.395(8) . ?
C19 C22 1.423(8) . ?
C46 C45 1.351(8) . ?
C46 H46 0.9300 . ?
C48 C49 1.383(8) . ?
C10 C11 1.367(8) . ?
C10 C9 1.503(8) . ?
C6 C7 1.370(8) . ?
C6 C5 1.396(8) . ?
C6 C8 1.446(7) . ?
C45 C50 1.365(9) . ?
C7 C2 1.403(7) . ?
C2 C3 1.369(8) . ?
C2 H2A 0.9300 . ?
C28 C27 1.368(8) . ?
C28 H28 0.9300 . ?
C16 C21 1.365(9) . ?
C16 C17 1.368(8) . ?
C37 C38 1.439(9) . ?
C35 C30 1.388(7) . ?
C35 H35 0.9300 . ?
C38 C39 1.391(8) . ?
C25 C26 1.379(9) . ?
C25 H25 0.9300 . ?
C33 C32 1.401(8) . ?
C33 C36 1.425(9) . ?
C53 C54 1.354(8) . ?
C53 H53 0.9300 . ?
C27 C26 1.351(8) . ?
C27 H27 0.9300 . ?
C22 H22 0.9300 . ?
C17 H17 0.9300 . ?
C30 C31 1.348(9) . ?
C26 H26 0.9300 . ?
C55 C54 1.352(9) . ?
C55 C56 1.383(8) . ?
C55 H55 0.9300 . ?
C3 C4 1.352(9) . ?
C50 C49 1.352(9) . ?
C50 H50 0.9300 . ?
C56 H56 0.9300 . ?
C13 C12 1.347(9) . ?
C13 C14 1.353(8) . ?
C13 H13 0.9300 . ?
C49 H49 0.9300 . ?
C39 C40 1.355(9) . ?
C39 H39 0.9300 . ?
C20 C21 1.354(9) . ?
C20 H20 0.9300 . ?
C8 H8B 0.9300 . ?
C4 C5 1.358(7) . ?
C4 H4 0.9300 . ?
C42 C41 1.389(8) . ?
C42 H42 0.9300 . ?
C54 H54 0.9300 . ?
C12 C11 1.394(8) . ?
C12 H12 0.9300 . ?
C21 H21 0.9300 . ?
C14 H14 0.9300 . ?
C36 H36 0.9300 . ?
C41 C40 1.371(8) . ?
C41 H41 0.9300 . ?
C40 H40 0.9300 . ?
C32 C31 1.346(10) . ?
C32 H32 0.9300 . ?
C11 H11B 0.9300 . ?
C31 H31 0.9300 . ?
C5 H5B 0.9300 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C18 O8 H8 109.5 . . ?
C34 O10 H10 109.5 . . ?
C7 O5 H5 109.5 . . ?
C30 O4 C29 119.5(5) . . ?
C47 O11 H11 109.5 . . ?
C16 O2 C15 119.3(5) . . ?
C3 O1 C1 119.1(5) . . ?
C45 O3 C44 118.4(6) . . ?
C51 N11 N10 120.0(6) . . ?
C51 N11 H11A 120.0 . . ?
N10 N11 H11A 120.0 . . ?
C00R N10 N11 114.8(6) . . ?
C23 N5 N4 119.2(5) . . ?
C23 N5 H5A 120.4 . . ?
N4 N5 H5A 120.4 . . ?
C22 N4 N5 115.8(5) . . ?
C24 N6 C28 118.1(5) . . ?
N7 N8 C37 120.0(5) . . ?
N7 N8 H8A 120.0 . . ?
C37 N8 H8A 120.0 . . ?
C10 N3 C14 117.6(6) . . ?
C36 N7 N8 115.5(6) . . ?
C8 N1 N2 113.2(6) . . ?
C52 N12 C56 118.6(6) . . ?
C9 N2 N1 116.7(6) . . ?
C9 N2 H2 121.6 . . ?
N1 N2 H2 121.6 . . ?
C42 N9 C38 118.5(6) . . ?
N12 C52 C53 122.5(6) . . ?
N12 C52 C51 117.6(6) . . ?
C53 C52 C51 119.8(7) . . ?
O11 C47 C48 120.8(6) . . ?
O11 C47 C46 117.8(6) . . ?
C48 C47 C46 121.4(6) . . ?
N10 C00R C48 119.5(7) . . ?
N10 C00R H00R 120.3 . . ?
C48 C00R H00R 120.3 . . ?
O12 C51 N11 122.5(6) . . ?
O12 C51 C52 122.8(7) . . ?
N11 C51 C52 114.7(7) . . ?
N6 C24 C25 122.5(6) . . ?
N6 C24 C23 117.1(6) . . ?
C25 C24 C23 120.4(6) . . ?
O8 C18 C19 122.5(6) . . ?
O8 C18 C17 115.4(5) . . ?
C19 C18 C17 122.0(6) . . ?
O10 C34 C35 116.2(5) . . ?
O10 C34 C33 120.9(7) . . ?
C35 C34 C33 122.8(5) . . ?
C18 C19 C20 117.0(6) . . ?
C18 C19 C22 123.6(6) . . ?
C20 C19 C22 119.3(6) . . ?
C45 C46 C47 119.7(7) . . ?
C45 C46 H46 120.1 . . ?
C47 C46 H46 120.1 . . ?
C47 C48 C49 116.8(6) . . ?
C47 C48 C00R 123.3(6) . . ?
C49 C48 C00R 119.8(7) . . ?
N3 C10 C11 122.9(6) . . ?
N3 C10 C9 117.3(6) . . ?
C11 C10 C9 119.8(7) . . ?
C7 C6 C5 117.9(5) . . ?
C7 C6 C8 123.4(6) . . ?
C5 C6 C8 118.7(6) . . ?
C46 C45 O3 124.6(7) . . ?
C46 C45 C50 120.0(6) . . ?
O3 C45 C50 115.4(7) . . ?
O5 C7 C6 123.6(5) . . ?
O5 C7 C2 115.2(6) . . ?
C6 C7 C2 121.2(6) . . ?
C3 C2 C7 117.9(6) . . ?
C3 C2 H2A 121.0 . . ?
C7 C2 H2A 121.0 . . ?
N6 C28 C27 122.2(6) . . ?
N6 C28 H28 118.9 . . ?
C27 C28 H28 118.9 . . ?
O6 C9 N2 126.4(6) . . ?
O6 C9 C10 121.1(6) . . ?
N2 C9 C10 112.5(7) . . ?
O2 C16 C21 116.3(6) . . ?
O2 C16 C17 122.4(6) . . ?
C21 C16 C17 121.2(7) . . ?
O9 C37 N8 121.7(7) . . ?
O9 C37 C38 123.5(6) . . ?
N8 C37 C38 114.8(5) . . ?
C34 C35 C30 118.1(6) . . ?
C34 C35 H35 121.0 . . ?
C30 C35 H35 121.0 . . ?
N9 C38 C39 120.1(7) . . ?
N9 C38 C37 118.6(6) . . ?
C39 C38 C37 121.2(6) . . ?
C24 C25 C26 119.0(6) . . ?
C24 C25 H25 120.5 . . ?
C26 C25 H25 120.5 . . ?
C34 C33 C32 115.6(7) . . ?
C34 C33 C36 124.3(5) . . ?
C32 C33 C36 120.0(6) . . ?
C54 C53 C52 119.0(7) . . ?
C54 C53 H53 120.5 . . ?
C52 C53 H53 120.5 . . ?
C26 C27 C28 120.1(6) . . ?
C26 C27 H27 120.0 . . ?
C28 C27 H27 120.0 . . ?
N4 C22 C19 120.8(6) . . ?
N4 C22 H22 119.6 . . ?
C19 C22 H22 119.6 . . ?
O7 C23 N5 123.8(7) . . ?
O7 C23 C24 122.1(6) . . ?
N5 C23 C24 114.0(6) . . ?
C16 C17 C18 118.2(6) . . ?
C16 C17 H17 120.9 . . ?
C18 C17 H17 120.9 . . ?
C31 C30 O4 117.2(6) . . ?
C31 C30 C35 120.8(8) . . ?
O4 C30 C35 121.9(7) . . ?
C27 C26 C25 118.0(6) . . ?
C27 C26 H26 121.0 . . ?
C25 C26 H26 121.0 . . ?
C54 C55 C56 119.7(7) . . ?
C54 C55 H55 120.1 . . ?
C56 C55 H55 120.1 . . ?
C4 C3 C2 121.9(5) . . ?
C4 C3 O1 117.0(6) . . ?
C2 C3 O1 121.0(7) . . ?
C49 C50 C45 120.0(7) . . ?
C49 C50 H50 120.0 . . ?
C45 C50 H50 120.0 . . ?
N12 C56 C55 121.2(7) . . ?
N12 C56 H56 119.4 . . ?
C55 C56 H56 119.4 . . ?
C12 C13 C14 118.2(6) . . ?
C12 C13 H13 120.9 . . ?
C14 C13 H13 120.9 . . ?
C50 C49 C48 122.0(7) . . ?
C50 C49 H49 119.0 . . ?
C48 C49 H49 119.0 . . ?
C40 C39 C38 119.9(6) . . ?
C40 C39 H39 120.1 . . ?
C38 C39 H39 120.1 . . ?
C21 C20 C19 121.9(6) . . ?
C21 C20 H20 119.1 . . ?
C19 C20 H20 119.1 . . ?
N1 C8 C6 118.9(6) . . ?
N1 C8 H8B 120.5 . . ?
C6 C8 H8B 120.5 . . ?
C3 C4 C5 119.8(6) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
N9 C42 C41 125.1(6) . . ?
N9 C42 H42 117.4 . . ?
C41 C42 H42 117.4 . . ?
C55 C54 C53 118.9(7) . . ?
C55 C54 H54 120.5 . . ?
C53 C54 H54 120.5 . . ?
C13 C12 C11 119.6(6) . . ?
C13 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C20 C21 C16 119.7(6) . . ?
C20 C21 H21 120.2 . . ?
C16 C21 H21 120.2 . . ?
N3 C14 C13 123.9(7) . . ?
N3 C14 H14 118.0 . . ?
C13 C14 H14 118.0 . . ?
N7 C36 C33 120.6(6) . . ?
N7 C36 H36 119.7 . . ?
C33 C36 H36 119.7 . . ?
C40 C41 C42 115.9(7) . . ?
C40 C41 H41 122.0 . . ?
C42 C41 H41 122.0 . . ?
C39 C40 C41 120.3(7) . . ?
C39 C40 H40 119.8 . . ?
C41 C40 H40 119.8 . . ?
C31 C32 C33 122.6(7) . . ?
C31 C32 H32 118.7 . . ?
C33 C32 H32 118.7 . . ?
C10 C11 C12 117.8(7) . . ?
C10 C11 H11B 121.1 . . ?
C12 C11 H11B 121.1 . . ?
C32 C31 C30 120.0(6) . . ?
C32 C31 H31 120.0 . . ?
C30 C31 H31 120.0 . . ?
C4 C5 C6 121.2(7) . . ?
C4 C5 H5B 119.4 . . ?
C6 C5 H5B 119.4 . . ?
O3 C44 H44A 109.5 . . ?
O3 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
O3 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O4 C29 H29A 109.5 . . ?
O4 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
O4 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_refine_diff_density_max         0.333
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.071

