# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_35dnp2o-nft
_database_code_depnum_ccdc_archive 'CCDC 2123841'
loop_
_audit_author_name
_audit_author_address
'Ivan Fedyanin'
;Institute of Organoelement Compounds of Russian Academy of Sciences (INEOS RAS)
Russia
;
_audit_update_record             
;
2021-11-23 deposited with the CCDC.	2022-02-24 downloaded from the CCDC.
;

_publ_contact_name               'Fedyanin, Ivan V.'
_publ_contact_email              octy@xrlab.ineos.ac.ru

_audit_creation_method           'Modified SHELXL output'
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H3 N3 O5, C10 H8'
_chemical_formula_sum            'C15 H11 N3 O5'
_chemical_formula_weight         313.27

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      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   7.1368(3)
_cell_length_b                   7.7530(3)
_cell_length_c                   12.3724(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.282(2)
_cell_angle_gamma                90
_cell_volume                     675.62(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9928
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      41.50

_exptl_crystal_description       prism
_exptl_crystal_colour_primary    yellow
_exptl_crystal_colour_modifier   greenish
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.540
_exptl_crystal_F_000             324
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.119
_shelx_estimated_absorpt_T_min   0.956
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.823
_exptl_absorpt_correction_T_max  0.863
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX DUO diffractometer'
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'ο scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37496
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_av_R_equivalents  0.0232
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.668
_diffrn_reflns_theta_max         43.503
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             10091
_reflns_number_gt                8667
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.883
_reflns_Friedel_fraction_max     0.968
_reflns_Friedel_fraction_full    1.000

_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 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0600P)²+0.0600P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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_abs_structure_details 
;
 Flack x determined using 3644 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(15)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         10091
_refine_ls_number_parameters     212
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0538
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1088
_refine_ls_wR_factor_gt          0.1019
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_restrained_S_all      1.015
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 1.07061(13) 0.32810(10) 0.99845(6) 0.02078(13) Uani 1 1 d . . . . .
O3 O 1.20819(14) 0.60360(12) 0.90435(8) 0.02791(17) Uani 1 1 d . . . . .
O4 O 1.07399(17) 0.65567(13) 0.73885(9) 0.0332(2) Uani 1 1 d . . . . .
O5 O 0.8763(2) 0.1733(2) 0.50480(8) 0.0544(4) Uani 1 1 d . . . . .
O6 O 0.82983(17) -0.07470(15) 0.57567(9) 0.0342(2) Uani 1 1 d . . . . .
N1 N 0.97104(12) 0.11517(10) 0.87945(6) 0.01524(11) Uani 1 1 d . . . . .
H1 H 0.958(3) 0.053(3) 0.9333(17) 0.028(5) Uiso 1 1 d . . . . .
N3 N 1.11467(12) 0.55984(11) 0.81740(7) 0.01808(13) Uani 1 1 d . . . . .
N5 N 0.87571(15) 0.07756(16) 0.58264(8) 0.02587(19) Uani 1 1 d . . . . .
C2 C 1.03471(13) 0.28217(11) 0.90263(7) 0.01451(12) Uani 1 1 d . . . . .
C3 C 1.04711(12) 0.38246(11) 0.80589(7) 0.01455(12) Uani 1 1 d . . . . .
C4 C 0.99438(14) 0.32048(13) 0.70291(7) 0.01697(13) Uani 1 1 d . . . . .
H4 H 1.000603 0.391066 0.640832 0.020 Uiso 1 1 calc R U . . .
C5 C 0.93057(13) 0.14980(13) 0.69055(7) 0.01683(13) Uani 1 1 d . . . . .
C6 C 0.92168(13) 0.04876(12) 0.77943(7) 0.01634(13) Uani 1 1 d . . . . .
H6 H 0.880822 -0.067722 0.770402 0.020 Uiso 1 1 calc R U . . .
C1N C 0.60533(15) 0.42818(15) 0.87129(9) 0.02198(17) Uani 1 1 d . . . . .
H1N H 0.634399 0.417597 0.948680 0.026 Uiso 1 1 calc R U . . .
C2N C 0.64156(16) 0.58011(15) 0.82243(11) 0.0257(2) Uani 1 1 d . . . . .
H2N H 0.693802 0.674659 0.866031 0.031 Uiso 1 1 calc R U . . .
C3N C 0.60173(17) 0.59682(14) 0.70789(11) 0.0261(2) Uani 1 1 d . . . . .
H3N H 0.628029 0.702374 0.674327 0.031 Uiso 1 1 calc R U . . .
C4N C 0.52534(16) 0.46183(13) 0.64462(9) 0.02162(17) Uani 1 1 d . . . . .
H4N H 0.499324 0.474270 0.567259 0.026 Uiso 1 1 calc R U . . .
C5N C 0.48467(13) 0.30412(12) 0.69294(7) 0.01577(13) Uani 1 1 d . . . . .
C6N C 0.40426(15) 0.16262(14) 0.62937(8) 0.02074(16) Uani 1 1 d . . . . .
H6N H 0.376110 0.173014 0.551946 0.025 Uiso 1 1 calc R U . . .
C7N C 0.36667(17) 0.01091(14) 0.67844(11) 0.0251(2) Uani 1 1 d . . . . .
H7N H 0.313828 -0.083513 0.634921 0.030 Uiso 1 1 calc R U . . .
C8N C 0.40615(17) -0.00545(15) 0.79314(12) 0.0263(2) Uani 1 1 d . . . . .
H8N H 0.378704 -0.110626 0.826753 0.032 Uiso 1 1 calc R U . . .
C9N C 0.48375(15) 0.12911(15) 0.85651(9) 0.02233(17) Uani 1 1 d . . . . .
H9N H 0.510062 0.116485 0.933852 0.027 Uiso 1 1 calc R U . . .
C10N C 0.52522(13) 0.28678(13) 0.80812(7) 0.01630(13) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C2 1.2247(11) . ?
O3 N3 1.2191(12) . ?
O4 N3 1.2206(12) . ?
O5 N5 1.2162(17) . ?
O6 N5 1.2244(16) . ?
N1 C6 1.3342(12) . ?
N1 C2 1.3867(12) . ?
N1 H1 0.84(2) . ?
N3 C3 1.4566(12) . ?
N5 C5 1.4426(12) . ?
C2 C3 1.4420(12) . ?
C3 C4 1.3569(12) . ?
C4 C5 1.3998(14) . ?
C4 H4 0.9500 . ?
C5 C6 1.3599(13) . ?
C6 H6 0.9500 . ?
C1N C2N 1.3676(18) . ?
C1N C10N 1.4125(15) . ?
C1N H1N 0.9500 . ?
C2N C3N 1.4056(19) . ?
C2N H2N 0.9500 . ?
C3N C4N 1.3666(17) . ?
C3N H3N 0.9500 . ?
C4N C5N 1.4117(14) . ?
C4N H4N 0.9500 . ?
C5N C10N 1.4141(12) . ?
C5N C6N 1.4163(14) . ?
C6N C7N 1.3698(16) . ?
C6N H6N 0.9500 . ?
C7N C8N 1.4073(19) . ?
C7N H7N 0.9500 . ?
C8N C9N 1.3674(18) . ?
C8N H8N 0.9500 . ?
C9N C10N 1.4133(14) . ?
C9N H9N 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
C6 N1 C2 125.51(8) . . ?
C6 N1 H1 117.8(15) . . ?
C2 N1 H1 116.6(15) . . ?
O3 N3 O4 124.00(10) . . ?
O3 N3 C3 118.33(8) . . ?
O4 N3 C3 117.67(9) . . ?
O5 N5 O6 124.58(11) . . ?
O5 N5 C5 117.45(11) . . ?
O6 N5 C5 117.97(11) . . ?
O2 C2 N1 118.83(8) . . ?
O2 C2 C3 127.98(9) . . ?
N1 C2 C3 113.18(7) . . ?
C4 C3 C2 122.92(8) . . ?
C4 C3 N3 117.61(8) . . ?
C2 C3 N3 119.44(8) . . ?
C3 C4 C5 118.26(8) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
C6 C5 C4 120.86(8) . . ?
C6 C5 N5 118.93(9) . . ?
C4 C5 N5 120.21(9) . . ?
N1 C6 C5 119.20(9) . . ?
N1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C2N C1N C10N 120.82(10) . . ?
C2N C1N H1N 119.6 . . ?
C10N C1N H1N 119.6 . . ?
C1N C2N C3N 120.21(10) . . ?
C1N C2N H2N 119.9 . . ?
C3N C2N H2N 119.9 . . ?
C4N C3N C2N 120.27(10) . . ?
C4N C3N H3N 119.9 . . ?
C2N C3N H3N 119.9 . . ?
C3N C4N C5N 120.73(10) . . ?
C3N C4N H4N 119.6 . . ?
C5N C4N H4N 119.6 . . ?
C4N C5N C10N 119.11(9) . . ?
C4N C5N C6N 121.89(9) . . ?
C10N C5N C6N 118.99(8) . . ?
C7N C6N C5N 120.65(10) . . ?
C7N C6N H6N 119.7 . . ?
C5N C6N H6N 119.7 . . ?
C6N C7N C8N 120.17(10) . . ?
C6N C7N H7N 119.9 . . ?
C8N C7N H7N 119.9 . . ?
C9N C8N C7N 120.41(10) . . ?
C9N C8N H8N 119.8 . . ?
C7N C8N H8N 119.8 . . ?
C8N C9N C10N 120.67(10) . . ?
C8N C9N H9N 119.7 . . ?
C10N C9N H9N 119.7 . . ?
C1N C10N C9N 122.05(9) . . ?
C1N C10N C5N 118.85(9) . . ?
C9N C10N C5N 119.10(9) . . ?

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 O2 178.08(9) . . . . ?
C6 N1 C2 C3 -1.01(13) . . . . ?
O2 C2 C3 C4 -176.58(10) . . . . ?
N1 C2 C3 C4 2.41(12) . . . . ?
O2 C2 C3 N3 1.93(14) . . . . ?
N1 C2 C3 N3 -179.08(8) . . . . ?
O3 N3 C3 C4 -160.81(9) . . . . ?
O4 N3 C3 C4 19.10(13) . . . . ?
O3 N3 C3 C2 20.61(13) . . . . ?
O4 N3 C3 C2 -159.49(10) . . . . ?
C2 C3 C4 C5 -1.96(14) . . . . ?
N3 C3 C4 C5 179.50(8) . . . . ?
C3 C4 C5 C6 -0.01(14) . . . . ?
C3 C4 C5 N5 -179.08(9) . . . . ?
O5 N5 C5 C6 176.50(13) . . . . ?
O6 N5 C5 C6 -2.67(16) . . . . ?
O5 N5 C5 C4 -4.41(17) . . . . ?
O6 N5 C5 C4 176.42(11) . . . . ?
C2 N1 C6 C5 -0.79(14) . . . . ?
C4 C5 C6 N1 1.36(14) . . . . ?
N5 C5 C6 N1 -179.56(9) . . . . ?
C10N C1N C2N C3N -0.89(16) . . . . ?
C1N C2N C3N C4N 0.46(17) . . . . ?
C2N C3N C4N C5N 0.21(17) . . . . ?
C3N C4N C5N C10N -0.43(15) . . . . ?
C3N C4N C5N C6N 179.54(10) . . . . ?
C4N C5N C6N C7N 179.84(10) . . . . ?
C10N C5N C6N C7N -0.19(14) . . . . ?
C5N C6N C7N C8N 0.59(16) . . . . ?
C6N C7N C8N C9N -0.57(17) . . . . ?
C7N C8N C9N C10N 0.15(16) . . . . ?
C2N C1N C10N C9N -179.07(10) . . . . ?
C2N C1N C10N C5N 0.66(14) . . . . ?
C8N C9N C10N C1N 179.98(10) . . . . ?
C8N C9N C10N C5N 0.25(14) . . . . ?
C4N C5N C10N C1N 0.00(13) . . . . ?
C6N C5N C10N C1N -179.97(9) . . . . ?
C4N C5N C10N C9N 179.74(9) . . . . ?
C6N C5N C10N C9N -0.23(13) . . . . ?

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
N1 H1 O2 0.84(2) 1.96(2) 2.7329(11) 152(2) 2_747 yes
N1 H1 O3 0.84(2) 2.52(2) 3.1469(12) 131.9(19) 2_747 yes

_refine_diff_density_max         0.694
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.073



####################################################################### 
# 
# 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_35dnp2o-ant-s2p2
_database_code_depnum_ccdc_archive 'CCDC 2123846'
loop_
_audit_author_name
_audit_author_address
'Ivan Fedyanin'
;Institute of Organoelement Compounds of Russian Academy of Sciences (INEOS RAS)
Russia
;
_audit_update_record             
;
2021-11-23 deposited with the CCDC.	2022-02-24 downloaded from the CCDC.
;

_publ_contact_name               'Fedyanin, Ivan V.'
_publ_contact_email              octy@xrlab.ineos.ac.ru

_audit_creation_method           'Modified SHELXL output'
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H10, 2(C5 H3 N3 O5)'
_chemical_formula_sum            'C24 H16 N6 O10'
_chemical_formula_weight         548.43

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                   11.3941(2)
_cell_length_b                   8.2165(2)
_cell_length_c                   12.7470(2)
_cell_angle_alpha                90
_cell_angle_beta                 107.6050(10)
_cell_angle_gamma                90
_cell_volume                     1137.48(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9869
_cell_measurement_theta_min      4.57
_cell_measurement_theta_max      72.47

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.601
_exptl_crystal_F_000             564
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.340
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    1.098
_shelx_estimated_absorpt_T_min   0.706
_shelx_estimated_absorpt_T_max   0.927
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.234
_exptl_absorpt_correction_T_max  0.470
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX DUO diffractometer'
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'ο and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21350
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_av_R_equivalents  0.0413
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.567
_diffrn_reflns_theta_max         72.686
_diffrn_reflns_theta_full        72.000
_diffrn_measured_fraction_theta_max 0.970
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             2197
_reflns_number_gt                2126
_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 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0400P)²+0.6000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0022(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2197
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0345
_refine_ls_R_factor_gt           0.0338
_refine_ls_wR_factor_ref         0.0844
_refine_ls_wR_factor_gt          0.0839
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.74881(9) 0.33029(11) 0.72783(7) 0.0249(2) Uani 1 1 d . . . . .
O3 O 0.75593(11) 0.07191(12) 0.59787(8) 0.0372(3) Uani 1 1 d . . . . .
O4 O 0.74090(9) 0.12743(11) 0.42854(7) 0.0286(2) Uani 1 1 d . . . . .
O5 O 0.90132(8) 0.63033(11) 0.34292(7) 0.0263(2) Uani 1 1 d . . . . .
O6 O 0.93076(9) 0.83248(11) 0.45761(8) 0.0290(2) Uani 1 1 d . . . . .
N1 N 0.80361(9) 0.56807(12) 0.66732(8) 0.0183(2) Uani 1 1 d . . . . .
H1 H 0.7929(14) 0.618(2) 0.7247(14) 0.028(4) Uiso 1 1 d . . . . .
N3 N 0.76069(9) 0.16669(12) 0.52519(8) 0.0212(2) Uani 1 1 d . . . . .
N5 N 0.89751(9) 0.69293(12) 0.42941(8) 0.0200(2) Uani 1 1 d . . . . .
C2 C 0.77906(10) 0.40092(14) 0.65599(9) 0.0180(2) Uani 1 1 d . . . . .
C3 C 0.79110(10) 0.33652(14) 0.55358(9) 0.0175(2) Uani 1 1 d . . . . .
C4 C 0.82580(10) 0.42942(14) 0.47974(9) 0.0178(2) Uani 1 1 d . . . . .
H4 H 0.830602 0.383657 0.412717 0.021 Uiso 1 1 calc R U . . .
C5 C 0.85430(10) 0.59345(14) 0.50408(9) 0.0176(2) Uani 1 1 d . . . . .
C6 C 0.83964(10) 0.66206(14) 0.59734(9) 0.0184(2) Uani 1 1 d . . . . .
H6 H 0.854882 0.774744 0.611939 0.022 Uiso 1 1 calc R U . . .
C1A C 0.55177(11) 0.48371(16) 0.29557(10) 0.0233(3) Uani 1 1 d . . . . .
H1A H 0.543189 0.384078 0.256155 0.028 Uiso 1 1 calc R U . . .
C2A C 0.59065(12) 0.61926(17) 0.25431(10) 0.0269(3) Uani 1 1 d . . . . .
H2A H 0.609739 0.612878 0.186858 0.032 Uiso 1 1 calc R U . . .
C3A C 0.60296(12) 0.77013(17) 0.31108(11) 0.0266(3) Uani 1 1 d . . . . .
H3A H 0.629940 0.863795 0.281218 0.032 Uiso 1 1 calc R U . . .
C4A C 0.57631(11) 0.78134(15) 0.40812(10) 0.0230(3) Uani 1 1 d . . . . .
H4A H 0.584199 0.883163 0.444922 0.028 Uiso 1 1 calc R U . . .
C5A C 0.53666(10) 0.64182(14) 0.45519(10) 0.0184(2) Uani 1 1 d . . . . .
C6A C 0.51248(10) 0.64829(14) 0.55638(10) 0.0193(3) Uani 1 1 d . . . . .
H6A H 0.520916 0.748974 0.594591 0.023 Uiso 1 1 calc R U . . .
C7A C 0.47628(10) 0.51045(14) 0.60250(9) 0.0187(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C2 1.2187(15) . ?
O3 N3 1.2241(14) . ?
O4 N3 1.2266(13) . ?
O5 N5 1.2293(13) . ?
O6 N5 1.2268(14) . ?
N1 C6 1.3350(15) . ?
N1 C2 1.4003(15) . ?
N1 H1 0.879(17) . ?
N3 C3 1.4568(15) . ?
N5 C5 1.4491(15) . ?
C2 C3 1.4530(16) . ?
C3 C4 1.3601(16) . ?
C4 C5 1.3991(16) . ?
C4 H4 0.9500 . ?
C5 C6 1.3707(16) . ?
C6 H6 0.9500 . ?
C1A C2A 1.3616(19) . ?
C1A C7A 1.4296(16) 3_666 ?
C1A H1A 0.9500 . ?
C2A C3A 1.421(2) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.3631(19) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.4291(17) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.3991(16) . ?
C5A C7A 1.4361(16) 3_666 ?
C6A C7A 1.3946(17) . ?
C6A H6A 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
C6 N1 C2 126.20(10) . . ?
C6 N1 H1 115.7(11) . . ?
C2 N1 H1 118.1(11) . . ?
O3 N3 O4 123.79(10) . . ?
O3 N3 C3 118.88(10) . . ?
O4 N3 C3 117.33(10) . . ?
O6 N5 O5 124.22(10) . . ?
O6 N5 C5 118.09(10) . . ?
O5 N5 C5 117.67(10) . . ?
O2 C2 N1 118.85(10) . . ?
O2 C2 C3 128.81(11) . . ?
N1 C2 C3 112.31(10) . . ?
C4 C3 C2 122.93(11) . . ?
C4 C3 N3 117.56(10) . . ?
C2 C3 N3 119.47(10) . . ?
C3 C4 C5 118.93(11) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 120.50(11) . . ?
C6 C5 N5 119.50(10) . . ?
C4 C5 N5 119.99(10) . . ?
N1 C6 C5 118.97(11) . . ?
N1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C2A C1A C7A 120.79(12) . 3_666 ?
C2A C1A H1A 119.6 . . ?
C7A C1A H1A 119.6 3_666 . ?
C1A C2A C3A 120.69(11) . . ?
C1A C2A H2A 119.7 . . ?
C3A C2A H2A 119.7 . . ?
C4A C3A C2A 120.43(12) . . ?
C4A C3A H3A 119.8 . . ?
C2A C3A H3A 119.8 . . ?
C3A C4A C5A 120.81(12) . . ?
C3A C4A H4A 119.6 . . ?
C5A C4A H4A 119.6 . . ?
C6A C5A C4A 122.14(11) . . ?
C6A C5A C7A 119.13(11) . 3_666 ?
C4A C5A C7A 118.71(11) . 3_666 ?
C7A C6A C5A 121.57(11) . . ?
C7A C6A H6A 119.2 . . ?
C5A C6A H6A 119.2 . . ?
C6A C7A C1A 122.13(11) . 3_666 ?
C6A C7A C5A 119.29(11) . 3_666 ?
C1A C7A C5A 118.56(11) 3_666 3_666 ?

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 O2 178.75(11) . . . . ?
C6 N1 C2 C3 -2.89(16) . . . . ?
O2 C2 C3 C4 179.89(12) . . . . ?
N1 C2 C3 C4 1.74(16) . . . . ?
O2 C2 C3 N3 2.26(19) . . . . ?
N1 C2 C3 N3 -175.90(10) . . . . ?
O3 N3 C3 C4 163.98(11) . . . . ?
O4 N3 C3 C4 -16.22(16) . . . . ?
O3 N3 C3 C2 -18.26(17) . . . . ?
O4 N3 C3 C2 161.54(11) . . . . ?
C2 C3 C4 C5 1.64(17) . . . . ?
N3 C3 C4 C5 179.32(10) . . . . ?
C3 C4 C5 C6 -4.28(17) . . . . ?
C3 C4 C5 N5 176.87(10) . . . . ?
O6 N5 C5 C6 6.77(16) . . . . ?
O5 N5 C5 C6 -175.01(10) . . . . ?
O6 N5 C5 C4 -174.37(11) . . . . ?
O5 N5 C5 C4 3.85(16) . . . . ?
C2 N1 C6 C5 0.48(17) . . . . ?
C4 C5 C6 N1 3.30(17) . . . . ?
N5 C5 C6 N1 -177.85(10) . . . . ?
C7A C1A C2A C3A -0.68(19) 3_666 . . . ?
C1A C2A C3A C4A 0.19(19) . . . . ?
C2A C3A C4A C5A 0.58(18) . . . . ?
C3A C4A C5A C6A 177.89(11) . . . . ?
C3A C4A C5A C7A -0.84(17) . . . 3_666 ?
C4A C5A C6A C7A -178.65(11) . . . . ?
C7A C5A C6A C7A 0.07(18) 3_666 . . . ?
C5A C6A C7A C1A -178.35(11) . . . 3_666 ?
C5A C6A C7A C5A -0.07(19) . . . 3_666 ?

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
N1 H1 O2 0.879(17) 1.951(17) 2.6959(13) 141.6(14) 2_656 yes
N1 H1 O3 0.879(17) 2.516(16) 3.2631(14) 143.3(14) 2_656 yes

_refine_diff_density_max         0.319
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.055




####################################################################### 
# 
# 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_35dnp2o-nft-s2
_database_code_depnum_ccdc_archive 'CCDC 2123844'
loop_
_audit_author_name
_audit_author_address
'Ivan Fedyanin'
;Institute of Organoelement Compounds of Russian Academy of Sciences (INEOS RAS)
Russia
;
_audit_update_record             
;
2021-11-23 deposited with the CCDC.	2022-02-24 downloaded from the CCDC.
;

_publ_contact_name               'Fedyanin, Ivan V.'
_publ_contact_email              octy@xrlab.ineos.ac.ru

_audit_creation_method           'Modified SHELXL output'
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H3 N3 O5, 1.5(C10 H8)'
_chemical_formula_sum            'C20 H15 N3 O5'
_chemical_formula_weight         377.35

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                   6.9648(2)
_cell_length_b                   8.0641(2)
_cell_length_c                   30.4792(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.7020(10)
_cell_angle_gamma                90
_cell_volume                     1711.10(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4645
_cell_measurement_theta_min      5.81
_cell_measurement_theta_max      72.50

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.899
_shelx_estimated_absorpt_T_min   0.732
_shelx_estimated_absorpt_T_max   0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.708
_exptl_absorpt_correction_T_max  0.864
_exptl_absorpt_process_details   TWINABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX DUO diffractometer'
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'ο and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            42289
_diffrn_reflns_av_unetI/netI     0.0444
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.901
_diffrn_reflns_theta_max         72.764
_diffrn_reflns_theta_full        72.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             42289
_reflns_number_gt                39193
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_refine_special_details          
;Refined as a 2-component twin.
 The twin law refined by SAINT software was 
     1.00003 -0.00009  0.00020
     0.00270  0.99701  0.02045
    -0.00432 -0.29193  0.99698,Twin
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0350P)²+0.8800P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         42289
_refine_ls_number_parameters     258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0407
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.1103
_refine_ls_wR_factor_gt          0.1088
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.60454(19) 0.74813(17) 0.24887(3) 0.0252(3) Uani 1 1 d . . . . .
O3 O 0.6714(2) 1.02159(17) 0.20072(4) 0.0294(3) Uani 1 1 d . . . . .
O4 O 0.7484(2) 0.98405(17) 0.13336(4) 0.0287(3) Uani 1 1 d . . . . .
O5 O 0.5715(2) 0.48346(19) 0.05800(4) 0.0364(4) Uani 1 1 d . . . . .
O6 O 0.4990(2) 0.26520(17) 0.09518(4) 0.0312(3) Uani 1 1 d . . . . .
N1 N 0.5288(2) 0.52100(19) 0.20855(5) 0.0186(3) Uani 1 1 d . . . . .
H1 H 0.496(3) 0.472(3) 0.2322(7) 0.025(5) Uiso 1 1 d . . . . .
N3 N 0.6873(2) 0.9338(2) 0.16801(4) 0.0198(3) Uani 1 1 d . . . . .
N5 N 0.5409(2) 0.4128(2) 0.09253(4) 0.0226(4) Uani 1 1 d . . . . .
C2 C 0.5889(2) 0.6858(2) 0.21232(5) 0.0182(4) Uani 1 1 d . . . . .
C3 C 0.6275(2) 0.7600(2) 0.17015(5) 0.0178(4) Uani 1 1 d . . . . .
C4 C 0.6129(2) 0.6746(2) 0.13177(5) 0.0180(4) Uani 1 1 d . . . . .
H4 H 0.641157 0.726742 0.104776 0.022 Uiso 1 1 calc R U . . .
C5 C 0.5553(2) 0.5081(2) 0.13271(5) 0.0183(4) Uani 1 1 d . . . . .
C6 C 0.5139(2) 0.4338(2) 0.17142(5) 0.0186(4) Uani 1 1 d . . . . .
H6 H 0.474806 0.320967 0.171976 0.022 Uiso 1 1 calc R U . . .
C1N C 0.1587(3) 0.8404(3) 0.19419(6) 0.0275(4) Uani 1 1 d . . . . .
H1N H 0.157405 0.851247 0.225216 0.033 Uiso 1 1 calc R U . . .
C2N C 0.2098(3) 0.9731(3) 0.16929(7) 0.0337(5) Uani 1 1 d . . . . .
H2N H 0.243492 1.075040 0.183098 0.040 Uiso 1 1 calc R U . . .
C3N C 0.2130(3) 0.9597(3) 0.12341(7) 0.0337(5) Uani 1 1 d . . . . .
H3N H 0.248802 1.052547 0.106303 0.040 Uiso 1 1 calc R U . . .
C4N C 0.1649(3) 0.8138(3) 0.10332(6) 0.0268(4) Uani 1 1 d . . . . .
H4N H 0.167766 0.806035 0.072242 0.032 Uiso 1 1 calc R U . . .
C5N C 0.1108(2) 0.6738(2) 0.12804(5) 0.0197(4) Uani 1 1 d . . . . .
C6N C 0.0608(3) 0.5203(3) 0.10822(6) 0.0240(4) Uani 1 1 d . . . . .
H6N H 0.062144 0.510085 0.077175 0.029 Uiso 1 1 calc R U . . .
C7N C 0.0107(3) 0.3867(3) 0.13291(6) 0.0276(4) Uani 1 1 d . . . . .
H7N H -0.021702 0.284597 0.119017 0.033 Uiso 1 1 calc R U . . .
C8N C 0.0071(3) 0.4001(3) 0.17886(6) 0.0290(5) Uani 1 1 d . . . . .
H8N H -0.028028 0.306918 0.195916 0.035 Uiso 1 1 calc R U . . .
C9N C 0.0539(3) 0.5466(3) 0.19917(6) 0.0256(4) Uani 1 1 d . . . . .
H9N H 0.050234 0.554070 0.230236 0.031 Uiso 1 1 calc R U . . .
C10N C 0.1075(2) 0.6871(2) 0.17459(5) 0.0204(4) Uani 1 1 d . . . . .
C1M C 0.7527(3) 0.9897(3) 0.02193(5) 0.0270(4) Uani 1 1 d . . . . .
H1M H 0.662381 1.060516 0.035278 0.032 Uiso 1 1 calc R U . . .
C2M C 0.7071(3) 0.8275(3) 0.01446(6) 0.0294(5) Uani 1 1 d . . . . .
H2M H 0.584914 0.786762 0.022356 0.035 Uiso 1 1 calc R U . . .
C3M C 0.8397(3) 0.7199(3) -0.00490(5) 0.0296(5) Uani 1 1 d . . . . .
H3M H 0.807023 0.606799 -0.009688 0.035 Uiso 1 1 calc R U . . .
C4M C 1.0155(3) 0.7777(3) -0.01681(5) 0.0265(4) Uani 1 1 d . . . . .
H4M H 1.104074 0.704131 -0.029758 0.032 Uiso 1 1 calc R U . . .
C5M C 1.0668(3) 0.9460(2) -0.01005(5) 0.0225(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C2 1.224(2) . ?
O3 N3 1.230(2) . ?
O4 N3 1.2193(19) . ?
O5 N5 1.221(2) . ?
O6 N5 1.229(2) . ?
N1 C6 1.334(2) . ?
N1 C2 1.397(2) . ?
N1 H1 0.86(2) . ?
N3 C3 1.464(2) . ?
N5 C5 1.447(2) . ?
C2 C3 1.450(2) . ?
C3 C4 1.359(2) . ?
C4 C5 1.401(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.362(2) . ?
C6 H6 0.9500 . ?
C1N C2N 1.365(3) . ?
C1N C10N 1.414(3) . ?
C1N H1N 0.9500 . ?
C2N C3N 1.403(3) . ?
C2N H2N 0.9500 . ?
C3N C4N 1.364(3) . ?
C3N H3N 0.9500 . ?
C4N C5N 1.415(3) . ?
C4N H4N 0.9500 . ?
C5N C6N 1.416(3) . ?
C5N C10N 1.424(2) . ?
C6N C7N 1.365(3) . ?
C6N H6N 0.9500 . ?
C7N C8N 1.406(3) . ?
C7N H7N 0.9500 . ?
C8N C9N 1.369(3) . ?
C8N H8N 0.9500 . ?
C9N C10N 1.415(3) . ?
C9N H9N 0.9500 . ?
C1M C2M 1.364(3) . ?
C1M C5M 1.417(3) 3_775 ?
C1M H1M 0.9500 . ?
C2M C3M 1.410(3) . ?
C2M H2M 0.9500 . ?
C3M C4M 1.369(3) . ?
C3M H3M 0.9500 . ?
C4M C5M 1.417(3) . ?
C4M H4M 0.9500 . ?
C5M C5M 1.426(4) 3_775 ?

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
C6 N1 C2 125.94(15) . . ?
C6 N1 H1 116.8(15) . . ?
C2 N1 H1 117.3(14) . . ?
O4 N3 O3 123.54(16) . . ?
O4 N3 C3 117.63(14) . . ?
O3 N3 C3 118.82(13) . . ?
O5 N5 O6 123.80(14) . . ?
O5 N5 C5 118.18(16) . . ?
O6 N5 C5 118.02(14) . . ?
O2 C2 N1 118.92(15) . . ?
O2 C2 C3 128.58(17) . . ?
N1 C2 C3 112.49(14) . . ?
C4 C3 C2 122.86(17) . . ?
C4 C3 N3 117.47(15) . . ?
C2 C3 N3 119.67(14) . . ?
C3 C4 C5 118.84(15) . . ?
C3 C4 H4 120.6 . . ?
C5 C4 H4 120.6 . . ?
C6 C5 C4 120.49(15) . . ?
C6 C5 N5 119.23(17) . . ?
C4 C5 N5 120.28(14) . . ?
N1 C6 C5 119.32(17) . . ?
N1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C2N C1N C10N 121.12(17) . . ?
C2N C1N H1N 119.4 . . ?
C10N C1N H1N 119.4 . . ?
C1N C2N C3N 120.4(2) . . ?
C1N C2N H2N 119.8 . . ?
C3N C2N H2N 119.8 . . ?
C4N C3N C2N 120.19(19) . . ?
C4N C3N H3N 119.9 . . ?
C2N C3N H3N 119.9 . . ?
C3N C4N C5N 121.01(17) . . ?
C3N C4N H4N 119.5 . . ?
C5N C4N H4N 119.5 . . ?
C4N C5N C6N 122.44(16) . . ?
C4N C5N C10N 118.87(17) . . ?
C6N C5N C10N 118.69(17) . . ?
C7N C6N C5N 121.20(16) . . ?
C7N C6N H6N 119.4 . . ?
C5N C6N H6N 119.4 . . ?
C6N C7N C8N 120.06(19) . . ?
C6N C7N H7N 120.0 . . ?
C8N C7N H7N 120.0 . . ?
C9N C8N C7N 120.39(18) . . ?
C9N C8N H8N 119.8 . . ?
C7N C8N H8N 119.8 . . ?
C8N C9N C10N 120.99(16) . . ?
C8N C9N H9N 119.5 . . ?
C10N C9N H9N 119.5 . . ?
C1N C10N C9N 122.93(16) . . ?
C1N C10N C5N 118.41(17) . . ?
C9N C10N C5N 118.66(17) . . ?
C2M C1M C5M 120.84(19) . 3_775 ?
C2M C1M H1M 119.6 . . ?
C5M C1M H1M 119.6 3_775 . ?
C1M C2M C3M 120.55(19) . . ?
C1M C2M H2M 119.7 . . ?
C3M C2M H2M 119.7 . . ?
C4M C3M C2M 120.2(2) . . ?
C4M C3M H3M 119.9 . . ?
C2M C3M H3M 119.9 . . ?
C3M C4M C5M 120.75(19) . . ?
C3M C4M H4M 119.6 . . ?
C5M C4M H4M 119.6 . . ?
C1M C5M C4M 122.36(18) 3_775 . ?
C1M C5M C5M 118.8(2) 3_775 3_775 ?
C4M C5M C5M 118.9(2) . 3_775 ?

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 O2 -176.54(17) . . . . ?
C6 N1 C2 C3 2.7(2) . . . . ?
O2 C2 C3 C4 176.84(18) . . . . ?
N1 C2 C3 C4 -2.3(2) . . . . ?
O2 C2 C3 N3 -2.4(3) . . . . ?
N1 C2 C3 N3 178.46(14) . . . . ?
O4 N3 C3 C4 -11.0(2) . . . . ?
O3 N3 C3 C4 168.07(16) . . . . ?
O4 N3 C3 C2 168.31(15) . . . . ?
O3 N3 C3 C2 -12.6(2) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
N3 C3 C4 C5 -179.76(15) . . . . ?
C3 C4 C5 C6 0.3(3) . . . . ?
C3 C4 C5 N5 -179.09(16) . . . . ?
O5 N5 C5 C6 177.28(17) . . . . ?
O6 N5 C5 C6 -2.9(2) . . . . ?
O5 N5 C5 C4 -3.3(2) . . . . ?
O6 N5 C5 C4 176.48(16) . . . . ?
C2 N1 C6 C5 -1.6(3) . . . . ?
C4 C5 C6 N1 0.0(3) . . . . ?
N5 C5 C6 N1 179.38(16) . . . . ?
C10N C1N C2N C3N -0.1(3) . . . . ?
C1N C2N C3N C4N 0.0(3) . . . . ?
C2N C3N C4N C5N 0.1(3) . . . . ?
C3N C4N C5N C6N -179.74(18) . . . . ?
C3N C4N C5N C10N -0.1(3) . . . . ?
C4N C5N C6N C7N 179.44(18) . . . . ?
C10N C5N C6N C7N -0.2(3) . . . . ?
C5N C6N C7N C8N 0.3(3) . . . . ?
C6N C7N C8N C9N -0.1(3) . . . . ?
C7N C8N C9N C10N -0.3(3) . . . . ?
C2N C1N C10N C9N 179.92(18) . . . . ?
C2N C1N C10N C5N 0.1(3) . . . . ?
C8N C9N C10N C1N -179.39(17) . . . . ?
C8N C9N C10N C5N 0.4(3) . . . . ?
C4N C5N C10N C1N 0.0(3) . . . . ?
C6N C5N C10N C1N 179.64(16) . . . . ?
C4N C5N C10N C9N -179.83(17) . . . . ?
C6N C5N C10N C9N -0.2(3) . . . . ?
C5M C1M C2M C3M 0.7(3) 3_775 . . . ?
C1M C2M C3M C4M -0.6(3) . . . . ?
C2M C3M C4M C5M -0.2(3) . . . . ?
C3M C4M C5M C1M 179.99(16) . . . 3_775 ?
C3M C4M C5M C5M 0.9(3) . . . 3_775 ?

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
N1 H1 O2 0.86(2) 2.02(2) 2.731(2) 139.0(19) 2_645 yes
N1 H1 O3 0.86(2) 2.42(2) 3.1340(19) 141.0(19) 2_645 yes

_refine_diff_density_max         0.198
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.057



####################################################################### 
# 
# 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_35dnp2o-ant-s2p1
_database_code_depnum_ccdc_archive 'CCDC 2123842'
loop_
_audit_author_name
_audit_author_address
'Ivan Fedyanin'
;Institute of Organoelement Compounds of Russian Academy of Sciences (INEOS RAS)
Russia
;
_audit_update_record             
;
2021-11-23 deposited with the CCDC.	2022-02-24 downloaded from the CCDC.
;

_publ_contact_name               'Fedyanin, Ivan V.'
_publ_contact_email              octy@xrlab.ineos.ac.ru

_audit_creation_method           'Modified SHELXL output'
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H10, 2(C5 H3 N3 O5)'
_chemical_formula_sum            'C24 H16 N6 O10'
_chemical_formula_weight         548.43

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                   20.2772(5)
_cell_length_b                   6.5794(2)
_cell_length_c                   17.0425(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.2871(16)
_cell_angle_gamma                90
_cell_volume                     2271.86(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4424
_cell_measurement_theta_min      4.36
_cell_measurement_theta_max      66.97

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.603
_exptl_crystal_F_000             1128
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.100
_shelx_estimated_absorpt_T_min   0.756
_shelx_estimated_absorpt_T_max   0.937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.791
_exptl_absorpt_correction_T_max  0.864
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX DUO diffractometer'
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'ο and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24792
_diffrn_reflns_av_unetI/netI     0.0334
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.181
_diffrn_reflns_theta_max         68.146
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.983
_reflns_number_total             4037
_reflns_number_gt                3159
_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 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0450P)²+0.4500P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         4037
_refine_ls_number_parameters     369
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0534
_refine_ls_R_factor_gt           0.0375
_refine_ls_wR_factor_ref         0.0949
_refine_ls_wR_factor_gt          0.0873
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.73092(6) 0.84650(19) 0.95804(7) 0.0256(3) Uani 1 1 d . . . . .
O3 O 0.81666(6) 0.8037(2) 1.08270(7) 0.0301(3) Uani 1 1 d . . . . .
O4 O 0.91830(6) 0.8860(2) 1.06526(8) 0.0354(3) Uani 1 1 d . . . . .
O5 O 1.00452(6) 0.8554(3) 0.80832(8) 0.0419(4) Uani 1 1 d . . . . .
O6 O 0.93768(6) 0.9076(2) 0.70732(7) 0.0388(4) Uani 1 1 d . . . . .
N1 N 0.77957(7) 0.8480(2) 0.84099(8) 0.0187(3) Uani 1 1 d . . . . .
H1 H 0.7380(11) 0.844(3) 0.8181(13) 0.039(6) Uiso 1 1 d . . . . .
N3 N 0.86222(7) 0.8473(2) 1.04036(8) 0.0232(3) Uani 1 1 d . . . . .
N5 N 0.94900(7) 0.8752(2) 0.77780(9) 0.0271(4) Uani 1 1 d . . . . .
C2 C 0.78255(8) 0.8479(3) 0.92320(9) 0.0191(4) Uani 1 1 d . . . . .
C3 C 0.84983(8) 0.8516(3) 0.95530(9) 0.0191(4) Uani 1 1 d . . . . .
C4 C 0.90322(8) 0.8606(3) 0.90958(10) 0.0196(4) Uani 1 1 d . . . . .
H4 H 0.946576 0.865648 0.932766 0.024 Uiso 1 1 calc R U . . .
C5 C 0.89331(8) 0.8622(3) 0.82810(10) 0.0194(4) Uani 1 1 d . . . . .
C6 C 0.83127(8) 0.8547(2) 0.79456(10) 0.0189(4) Uani 1 1 d . . . . .
H6 H 0.824759 0.854128 0.739052 0.023 Uiso 1 1 calc R U . . .
O2' O 0.71019(5) 0.83381(19) 0.69923(7) 0.0227(3) Uani 1 1 d . . . . .
O3' O 0.62488(6) 0.8514(2) 0.81978(7) 0.0304(3) Uani 1 1 d . . . . .
O4' O 0.52989(6) 0.9822(2) 0.78557(7) 0.0284(3) Uani 1 1 d . . . . .
O5' O 0.43240(6) 0.7909(2) 0.53658(8) 0.0349(3) Uani 1 1 d . . . . .
O6' O 0.49461(6) 0.7021(2) 0.44199(8) 0.0373(4) Uani 1 1 d . . . . .
N1' N 0.65884(7) 0.7704(2) 0.58122(8) 0.0196(3) Uani 1 1 d . . . . .
H1' H 0.6975(10) 0.744(3) 0.5616(12) 0.029(5) Uiso 1 1 d . . . . .
N3' N 0.58187(7) 0.8979(2) 0.77046(8) 0.0218(3) Uani 1 1 d . . . . .
N5' N 0.48659(7) 0.7555(2) 0.51026(9) 0.0253(3) Uani 1 1 d . . . . .
C2' C 0.65827(8) 0.8183(2) 0.66171(10) 0.0183(4) Uani 1 1 d . . . . .
C3' C 0.59187(8) 0.8481(2) 0.68805(9) 0.0185(4) Uani 1 1 d . . . . .
C4' C 0.53729(8) 0.8327(3) 0.64002(10) 0.0199(4) Uani 1 1 d . . . . .
H4' H 0.494779 0.858238 0.659364 0.024 Uiso 1 1 calc R U . . .
C5' C 0.54451(8) 0.7788(3) 0.56158(10) 0.0199(4) Uani 1 1 d . . . . .
C6' C 0.60562(8) 0.7475(3) 0.53309(10) 0.0208(4) Uani 1 1 d . . . . .
H6' H 0.610305 0.709974 0.479778 0.025 Uiso 1 1 calc R U . . .
C1C C 0.74865(10) 0.3325(3) 0.66592(10) 0.0263(4) Uani 1 1 d . . . . .
H1C H 0.782045 0.329971 0.628397 0.032 Uiso 1 1 calc R U . . .
C2C C 0.68423(10) 0.3239(3) 0.64086(11) 0.0318(5) Uani 1 1 d . . . . .
H2C H 0.673249 0.311449 0.586357 0.038 Uiso 1 1 calc R U . . .
C3C C 0.63348(10) 0.3333(3) 0.69512(12) 0.0316(5) Uani 1 1 d . . . . .
H3C H 0.588597 0.330067 0.676905 0.038 Uiso 1 1 calc R U . . .
C4C C 0.64862(9) 0.3470(3) 0.77301(11) 0.0255(4) Uani 1 1 d . . . . .
H4C H 0.613938 0.354265 0.808772 0.031 Uiso 1 1 calc R U . . .
C5C C 0.71530(8) 0.3508(3) 0.80267(10) 0.0209(4) Uani 1 1 d . . . . .
C6C C 0.73251(8) 0.3585(3) 0.88267(10) 0.0208(4) Uani 1 1 d . . . . .
H6C H 0.698635 0.363351 0.919556 0.025 Uiso 1 1 calc R U . . .
C7C C 0.79796(8) 0.3594(2) 0.90957(10) 0.0197(4) Uani 1 1 d . . . . .
C8C C 0.81627(9) 0.3663(3) 0.99156(10) 0.0246(4) Uani 1 1 d . . . . .
H8C H 0.782779 0.375639 1.028819 0.029 Uiso 1 1 calc R U . . .
C9C C 0.88036(10) 0.3598(3) 1.01707(11) 0.0304(4) Uani 1 1 d . . . . .
H9C H 0.891302 0.363049 1.071781 0.036 Uiso 1 1 calc R U . . .
C10C C 0.93094(9) 0.3482(3) 0.96276(12) 0.0309(4) Uani 1 1 d . . . . .
H10C H 0.975680 0.340727 0.981318 0.037 Uiso 1 1 calc R U . . .
C11C C 0.91644(9) 0.3475(3) 0.88426(11) 0.0257(4) Uani 1 1 d . . . . .
H11C H 0.951275 0.343569 0.848632 0.031 Uiso 1 1 calc R U . . .
C12C C 0.84979(8) 0.3528(3) 0.85454(10) 0.0203(4) Uani 1 1 d . . . . .
C13C C 0.83287(8) 0.3479(3) 0.77432(10) 0.0210(4) Uani 1 1 d . . . . .
H13C H 0.866810 0.346502 0.737478 0.025 Uiso 1 1 calc R U . . .
C14C C 0.76712(8) 0.3452(3) 0.74736(10) 0.0207(4) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C2 1.224(2) . ?
O3 N3 1.2288(19) . ?
O4 N3 1.2245(19) . ?
O5 N5 1.2280(19) . ?
O6 N5 1.232(2) . ?
N1 C6 1.339(2) . ?
N1 C2 1.400(2) . ?
N1 H1 0.92(2) . ?
N3 C3 1.462(2) . ?
N5 C5 1.447(2) . ?
C2 C3 1.450(2) . ?
C3 C4 1.360(2) . ?
C4 C5 1.395(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.362(2) . ?
C6 H6 0.9500 . ?
O2' C2' 1.214(2) . ?
O3' N3' 1.2257(18) . ?
O4' N3' 1.2272(18) . ?
O5' N5' 1.2257(19) . ?
O6' N5' 1.232(2) . ?
N1' C6' 1.338(2) . ?
N1' C2' 1.408(2) . ?
N1' H1' 0.88(2) . ?
N3' C3' 1.464(2) . ?
N5' C5' 1.444(2) . ?
C2' C3' 1.450(2) . ?
C3' C4' 1.354(2) . ?
C4' C5' 1.396(2) . ?
C4' H4' 0.9500 . ?
C5' C6' 1.364(2) . ?
C6' H6' 0.9500 . ?
C1C C2C 1.359(3) . ?
C1C C14C 1.425(2) . ?
C1C H1C 0.9500 . ?
C2C C3C 1.412(3) . ?
C2C H2C 0.9500 . ?
C3C C4C 1.354(3) . ?
C3C H3C 0.9500 . ?
C4C C5C 1.425(2) . ?
C4C H4C 0.9500 . ?
C5C C6C 1.395(2) . ?
C5C C14C 1.440(2) . ?
C6C C7C 1.387(2) . ?
C6C H6C 0.9500 . ?
C7C C8C 1.432(2) . ?
C7C C12C 1.437(2) . ?
C8C C9C 1.355(3) . ?
C8C H8C 0.9500 . ?
C9C C10C 1.411(3) . ?
C9C H9C 0.9500 . ?
C10C C11C 1.358(3) . ?
C10C H10C 0.9500 . ?
C11C C12C 1.425(2) . ?
C11C H11C 0.9500 . ?
C12C C13C 1.397(2) . ?
C13C C14C 1.393(2) . ?
C13C H13C 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
C6 N1 C2 126.00(15) . . ?
C6 N1 H1 118.6(13) . . ?
C2 N1 H1 115.4(13) . . ?
O4 N3 O3 123.69(14) . . ?
O4 N3 C3 117.39(14) . . ?
O3 N3 C3 118.91(14) . . ?
O5 N5 O6 124.27(15) . . ?
O5 N5 C5 117.81(15) . . ?
O6 N5 C5 117.91(14) . . ?
O2 C2 N1 118.80(15) . . ?
O2 C2 C3 128.85(15) . . ?
N1 C2 C3 112.34(14) . . ?
C4 C3 C2 122.89(15) . . ?
C4 C3 N3 117.38(15) . . ?
C2 C3 N3 119.73(14) . . ?
C3 C4 C5 118.97(15) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 120.75(15) . . ?
C6 C5 N5 118.89(15) . . ?
C4 C5 N5 120.35(15) . . ?
N1 C6 C5 119.02(15) . . ?
N1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C6' N1' C2' 125.78(15) . . ?
C6' N1' H1' 116.9(13) . . ?
C2' N1' H1' 117.1(13) . . ?
O3' N3' O4' 124.22(14) . . ?
O3' N3' C3' 118.69(14) . . ?
O4' N3' C3' 117.09(13) . . ?
O5' N5' O6' 123.62(15) . . ?
O5' N5' C5' 118.51(14) . . ?
O6' N5' C5' 117.87(14) . . ?
O2' C2' N1' 119.42(15) . . ?
O2' C2' C3' 128.48(15) . . ?
N1' C2' C3' 112.08(14) . . ?
C4' C3' C2' 123.34(15) . . ?
C4' C3' N3' 117.10(15) . . ?
C2' C3' N3' 119.55(14) . . ?
C3' C4' C5' 118.91(16) . . ?
C3' C4' H4' 120.5 . . ?
C5' C4' H4' 120.5 . . ?
C6' C5' C4' 120.69(16) . . ?
C6' C5' N5' 119.77(15) . . ?
C4' C5' N5' 119.54(15) . . ?
N1' C6' C5' 119.13(16) . . ?
N1' C6' H6' 120.4 . . ?
C5' C6' H6' 120.4 . . ?
C2C C1C C14C 121.36(17) . . ?
C2C C1C H1C 119.3 . . ?
C14C C1C H1C 119.3 . . ?
C1C C2C C3C 120.58(17) . . ?
C1C C2C H2C 119.7 . . ?
C3C C2C H2C 119.7 . . ?
C4C C3C C2C 120.17(17) . . ?
C4C C3C H3C 119.9 . . ?
C2C C3C H3C 119.9 . . ?
C3C C4C C5C 121.61(17) . . ?
C3C C4C H4C 119.2 . . ?
C5C C4C H4C 119.2 . . ?
C6C C5C C4C 122.98(16) . . ?
C6C C5C C14C 118.70(15) . . ?
C4C C5C C14C 118.32(16) . . ?
C7C C6C C5C 121.48(15) . . ?
C7C C6C H6C 119.3 . . ?
C5C C6C H6C 119.3 . . ?
C6C C7C C8C 122.02(15) . . ?
C6C C7C C12C 119.96(15) . . ?
C8C C7C C12C 118.03(15) . . ?
C9C C8C C7C 121.35(17) . . ?
C9C C8C H8C 119.3 . . ?
C7C C8C H8C 119.3 . . ?
C8C C9C C10C 120.30(17) . . ?
C8C C9C H9C 119.9 . . ?
C10C C9C H9C 119.9 . . ?
C11C C10C C9C 120.79(17) . . ?
C11C C10C H10C 119.6 . . ?
C9C C10C H10C 119.6 . . ?
C10C C11C C12C 121.00(17) . . ?
C10C C11C H11C 119.5 . . ?
C12C C11C H11C 119.5 . . ?
C13C C12C C11C 122.69(16) . . ?
C13C C12C C7C 118.82(15) . . ?
C11C C12C C7C 118.48(16) . . ?
C14C C13C C12C 121.19(15) . . ?
C14C C13C H13C 119.4 . . ?
C12C C13C H13C 119.4 . . ?
C13C C14C C1C 122.20(16) . . ?
C13C C14C C5C 119.84(15) . . ?
C1C C14C C5C 117.94(15) . . ?

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 O2 178.19(16) . . . . ?
C6 N1 C2 C3 -1.2(2) . . . . ?
O2 C2 C3 C4 -177.44(17) . . . . ?
N1 C2 C3 C4 1.9(2) . . . . ?
O2 C2 C3 N3 2.1(3) . . . . ?
N1 C2 C3 N3 -178.61(14) . . . . ?
O4 N3 C3 C4 11.9(2) . . . . ?
O3 N3 C3 C4 -167.36(15) . . . . ?
O4 N3 C3 C2 -167.61(15) . . . . ?
O3 N3 C3 C2 13.1(2) . . . . ?
C2 C3 C4 C5 -1.3(3) . . . . ?
N3 C3 C4 C5 179.17(14) . . . . ?
C3 C4 C5 C6 -0.1(3) . . . . ?
C3 C4 C5 N5 178.93(15) . . . . ?
O5 N5 C5 C6 -170.78(16) . . . . ?
O6 N5 C5 C6 10.0(2) . . . . ?
O5 N5 C5 C4 10.2(2) . . . . ?
O6 N5 C5 C4 -169.03(16) . . . . ?
C2 N1 C6 C5 0.0(3) . . . . ?
C4 C5 C6 N1 0.8(2) . . . . ?
N5 C5 C6 N1 -178.26(15) . . . . ?
C6' N1' C2' O2' 179.60(16) . . . . ?
C6' N1' C2' C3' -1.9(2) . . . . ?
O2' C2' C3' C4' 177.83(17) . . . . ?
N1' C2' C3' C4' -0.5(2) . . . . ?
O2' C2' C3' N3' -2.0(3) . . . . ?
N1' C2' C3' N3' 179.64(14) . . . . ?
O3' N3' C3' C4' 157.11(16) . . . . ?
O4' N3' C3' C4' -22.0(2) . . . . ?
O3' N3' C3' C2' -23.0(2) . . . . ?
O4' N3' C3' C2' 157.93(15) . . . . ?
C2' C3' C4' C5' 2.2(3) . . . . ?
N3' C3' C4' C5' -177.89(15) . . . . ?
C3' C4' C5' C6' -1.8(3) . . . . ?
C3' C4' C5' N5' 178.03(15) . . . . ?
O5' N5' C5' C6' -177.64(16) . . . . ?
O6' N5' C5' C6' 1.9(2) . . . . ?
O5' N5' C5' C4' 2.5(2) . . . . ?
O6' N5' C5' C4' -177.95(16) . . . . ?
C2' N1' C6' C5' 2.4(3) . . . . ?
C4' C5' C6' N1' -0.4(3) . . . . ?
N5' C5' C6' N1' 179.77(15) . . . . ?
C14C C1C C2C C3C 1.9(3) . . . . ?
C1C C2C C3C C4C -1.3(3) . . . . ?
C2C C3C C4C C5C -0.5(3) . . . . ?
C3C C4C C5C C6C -177.99(17) . . . . ?
C3C C4C C5C C14C 1.6(3) . . . . ?
C4C C5C C6C C7C 179.15(16) . . . . ?
C14C C5C C6C C7C -0.5(2) . . . . ?
C5C C6C C7C C8C -179.69(16) . . . . ?
C5C C6C C7C C12C 0.2(2) . . . . ?
C6C C7C C8C C9C 177.64(17) . . . . ?
C12C C7C C8C C9C -2.2(3) . . . . ?
C7C C8C C9C C10C 0.7(3) . . . . ?
C8C C9C C10C C11C 1.4(3) . . . . ?
C9C C10C C11C C12C -1.8(3) . . . . ?
C10C C11C C12C C13C -178.60(17) . . . . ?
C10C C11C C12C C7C 0.2(3) . . . . ?
C6C C7C C12C C13C 0.7(2) . . . . ?
C8C C7C C12C C13C -179.39(15) . . . . ?
C6C C7C C12C C11C -178.11(16) . . . . ?
C8C C7C C12C C11C 1.8(2) . . . . ?
C11C C12C C13C C14C 177.44(16) . . . . ?
C7C C12C C13C C14C -1.4(2) . . . . ?
C12C C13C C14C C1C -177.58(16) . . . . ?
C12C C13C C14C C5C 1.1(3) . . . . ?
C2C C1C C14C C13C 178.03(17) . . . . ?
C2C C1C C14C C5C -0.6(3) . . . . ?
C6C C5C C14C C13C -0.1(2) . . . . ?
C4C C5C C14C C13C -179.78(16) . . . . ?
C6C C5C C14C C1C 178.57(15) . . . . ?
C4C C5C C14C C1C -1.1(2) . . . . ?

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
N1 H1 O2' 0.92(2) 2.08(2) 2.7483(18) 128.6(18) . yes
N1 H1 O3' 0.92(2) 2.29(2) 3.1431(19) 154.0(18) . yes
N1' H1' O2 0.88(2) 2.01(2) 2.7165(18) 136.8(17) 4_575 yes
N1' H1' O3 0.88(2) 2.45(2) 3.236(2) 148.9(17) 4_575 yes

_refine_diff_density_max         0.195
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.047




####################################################################### 
# 
# 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_35dnp2o-acnft
_database_code_depnum_ccdc_archive 'CCDC 2123845'
loop_
_audit_author_name
_audit_author_address
'Ivan Fedyanin'
;Institute of Organoelement Compounds of Russian Academy of Sciences (INEOS RAS)
Russia
;
_audit_update_record             
;
2021-11-23 deposited with the CCDC.	2022-02-24 downloaded from the CCDC.
;

_publ_contact_name               'Fedyanin, Ivan V.'
_publ_contact_email              octy@xrlab.ineos.ac.ru

_audit_creation_method           'Modified SHELXL output'
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C5 H3 N3 O5, C12 H8'
_chemical_formula_sum            'C17 H11 N3 O5'
_chemical_formula_weight         337.29

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   7.9898(3)
_cell_length_b                   7.0018(3)
_cell_length_c                   25.9225(11)
_cell_angle_alpha                90
_cell_angle_beta                 91.907(2)
_cell_angle_gamma                90
_cell_volume                     1449.38(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4892
_cell_measurement_theta_min      3.41
_cell_measurement_theta_max      72.03

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.546
_exptl_crystal_F_000             696
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    0.986
_shelx_estimated_absorpt_T_min   0.665
_shelx_estimated_absorpt_T_max   0.874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.543
_exptl_absorpt_correction_T_max  0.864
_exptl_absorpt_process_details   TWINABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX DUO diffractometer'
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'ο and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            36677
_diffrn_reflns_av_unetI/netI     0.0315
_diffrn_reflns_av_R_equivalents  0.0539
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.705
_diffrn_reflns_theta_max         72.319
_diffrn_reflns_theta_full        68.000
_diffrn_measured_fraction_theta_max 0.925
_diffrn_measured_fraction_theta_full 0.949
_diffrn_reflns_Laue_measured_fraction_max 0.925
_diffrn_reflns_Laue_measured_fraction_full 0.949
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_point_group_measured_fraction_full 0.933
_reflns_number_total             5376
_reflns_number_gt                5351
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.797
_reflns_Friedel_fraction_max     0.878
_reflns_Friedel_fraction_full    0.913

_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_refine_special_details          
;Refined as a 2-component twin.
 Twin law refined by SAINT was
     1.00001 -0.00019  0.00007
    -0.00015 -1.00000 -0.00005
    -0.21520  0.00071 -1.00001,Twin
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0550P)²+0.5000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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_abs_structure_details 
;
 Flack x determined using 2335 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(7)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5376
_refine_ls_number_parameters     460
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_ref         0.0886
_refine_ls_wR_factor_gt          0.0885
_refine_ls_goodness_of_fit_ref   1.001
_refine_ls_restrained_S_all      1.001
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.0428(4) 0.8707(4) 0.24829(10) 0.0264(6) Uani 1 1 d . . . . .
O3 O -0.2333(4) 0.9695(5) 0.19217(12) 0.0341(7) Uani 1 1 d . . . . .
O4 O -0.2021(4) 1.0641(4) 0.11353(11) 0.0297(6) Uani 1 1 d . . . . .
O5 O 0.3081(4) 0.9588(5) 0.02743(11) 0.0317(7) Uani 1 1 d . . . . .
O6 O 0.5173(4) 0.8233(5) 0.06829(11) 0.0297(7) Uani 1 1 d . . . . .
N1 N 0.2699(4) 0.8169(4) 0.20091(13) 0.0194(7) Uani 1 1 d . . . . .
H1 H 0.324(7) 0.783(8) 0.227(2) 0.032(13) Uiso 1 1 d . . . . .
N3 N -0.1474(4) 0.9933(5) 0.15404(13) 0.0216(7) Uani 1 1 d . . . . .
N5 N 0.3770(4) 0.8890(5) 0.06645(13) 0.0226(7) Uani 1 1 d . . . . .
C2 C 0.1051(5) 0.8748(5) 0.20563(15) 0.0190(7) Uani 1 1 d . . . . .
C3 C 0.0272(5) 0.9354(5) 0.15674(14) 0.0178(7) Uani 1 1 d . . . . .
C4 C 0.1135(5) 0.9417(5) 0.11233(14) 0.0195(8) Uani 1 1 d . . . . .
H4 H 0.060145 0.984459 0.081131 0.023 Uiso 1 1 calc R U . . .
C5 C 0.2798(5) 0.8851(5) 0.11309(15) 0.0186(7) Uani 1 1 d . . . . .
C6 C 0.3577(5) 0.8201(5) 0.15784(15) 0.0199(7) Uani 1 1 d . . . . .
H6 H 0.470941 0.778621 0.158162 0.024 Uiso 1 1 calc R U . . .
O2' O 0.5478(3) 0.6637(4) 0.25143(10) 0.0240(6) Uani 1 1 d . . . . .
O3' O 0.2759(4) 0.6028(5) 0.30975(11) 0.0317(7) Uani 1 1 d . . . . .
O4' O 0.3257(4) 0.4707(4) 0.38425(11) 0.0300(6) Uani 1 1 d . . . . .
O5' O 0.8486(4) 0.5629(5) 0.47302(11) 0.0350(7) Uani 1 1 d . . . . .
O6' O 1.0562(4) 0.6950(5) 0.43441(11) 0.0338(7) Uani 1 1 d . . . . .
N1' N 0.7851(4) 0.7146(5) 0.29999(12) 0.0200(7) Uani 1 1 d . . . . .
H1' H 0.826(7) 0.781(7) 0.2717(19) 0.030(12) Uiso 1 1 d . . . . .
N3' N 0.3719(4) 0.5552(5) 0.34563(13) 0.0225(7) Uani 1 1 d . . . . .
N5' N 0.9137(4) 0.6339(5) 0.43483(12) 0.0226(7) Uani 1 1 d . . . . .
C2' C 0.6172(5) 0.6611(5) 0.29477(15) 0.0189(7) Uani 1 1 d . . . . .
C3' C 0.5484(5) 0.6025(5) 0.34322(14) 0.0179(7) Uani 1 1 d . . . . .
C4' C 0.6424(5) 0.5904(5) 0.38791(14) 0.0184(7) Uani 1 1 d . . . . .
H4' H 0.593908 0.547684 0.418825 0.022 Uiso 1 1 calc R U . . .
C5' C 0.8099(5) 0.6412(5) 0.38757(14) 0.0194(7) Uani 1 1 d . . . . .
C6' C 0.8815(5) 0.7056(6) 0.34356(15) 0.0212(7) Uani 1 1 d . . . . .
H6' H 0.995829 0.742786 0.343747 0.025 Uiso 1 1 calc R U . . .
C1M C 0.2300(7) 0.3365(6) 0.19799(18) 0.0338(10) Uani 1 1 d . . . . .
H1M H 0.242760 0.307886 0.233722 0.041 Uiso 1 1 calc R U . . .
C2M C 0.3502(6) 0.3203(6) 0.16371(19) 0.0340(10) Uani 1 1 d . . . . .
H2M H 0.461117 0.276737 0.170978 0.041 Uiso 1 1 calc R U . . .
C3M C 0.2825(6) 0.3809(6) 0.11281(18) 0.0289(9) Uani 1 1 d . . . . .
C4M C 0.3461(6) 0.4022(6) 0.06402(19) 0.0337(10) Uani 1 1 d . . . . .
H4M H 0.458630 0.369152 0.057315 0.040 Uiso 1 1 calc R U . . .
C5M C 0.2368(6) 0.4752(6) 0.02445(16) 0.0333(10) Uani 1 1 d . . . . .
H5M H 0.279227 0.490664 -0.009105 0.040 Uiso 1 1 calc R U . . .
C6M C 0.0734(6) 0.5247(6) 0.03206(17) 0.0325(10) Uani 1 1 d . . . . .
H6M H 0.006251 0.575723 0.004437 0.039 Uiso 1 1 calc R U . . .
C7M C 0.0044(5) 0.4990(5) 0.08196(15) 0.0251(8) Uani 1 1 d . . . . .
C8M C 0.1152(5) 0.4306(5) 0.11943(15) 0.0218(8) Uani 1 1 d . . . . .
C9M C -0.1602(5) 0.5435(6) 0.09696(18) 0.0306(9) Uani 1 1 d . . . . .
H9M H -0.241009 0.590701 0.072441 0.037 Uiso 1 1 calc R U . . .
C10M C -0.2008(6) 0.5173(6) 0.14734(19) 0.0332(10) Uani 1 1 d . . . . .
H10M H -0.311754 0.545363 0.157007 0.040 Uiso 1 1 calc R U . . .
C11M C -0.0853(6) 0.4505(6) 0.18565(17) 0.0323(10) Uani 1 1 d . . . . .
H11M H -0.117833 0.436839 0.220372 0.039 Uiso 1 1 calc R U . . .
C12M C 0.0742(6) 0.4057(6) 0.17211(16) 0.0287(9) Uani 1 1 d . . . . .
C1N C 0.4092(7) 0.0760(7) 0.32004(18) 0.0375(11) Uani 1 1 d . . . . .
H1N H 0.299417 0.055506 0.305953 0.045 Uiso 1 1 calc R U . . .
C2N C 0.5418(7) 0.1360(6) 0.29377(18) 0.0364(10) Uani 1 1 d . . . . .
H2N H 0.540404 0.163459 0.257869 0.044 Uiso 1 1 calc R U . . .
C3N C 0.6879(6) 0.1525(6) 0.32868(16) 0.0290(9) Uani 1 1 d . . . . .
C4N C 0.8519(6) 0.1986(6) 0.32438(18) 0.0338(10) Uani 1 1 d . . . . .
H4N H 0.893258 0.232974 0.291721 0.041 Uiso 1 1 calc R U . . .
C5N C 0.9610(6) 0.1955(6) 0.3684(2) 0.0352(10) Uani 1 1 d . . . . .
H5N H 1.074805 0.231328 0.364878 0.042 Uiso 1 1 calc R U . . .
C6N C 0.9067(6) 0.1418(6) 0.41635(18) 0.0321(10) Uani 1 1 d . . . . .
H6N H 0.982767 0.140646 0.445311 0.039 Uiso 1 1 calc R U . . .
C7N C 0.7381(6) 0.0888(6) 0.42218(16) 0.0265(8) Uani 1 1 d . . . . .
C8N C 0.6337(5) 0.0989(5) 0.37799(16) 0.0237(8) Uani 1 1 d . . . . .
C9N C 0.6586(7) 0.0179(6) 0.46737(18) 0.0358(11) Uani 1 1 d . . . . .
H9N H 0.720434 0.006453 0.499154 0.043 Uiso 1 1 calc R U . . .
C10N C 0.4955(6) -0.0322(7) 0.46422(19) 0.0381(11) Uani 1 1 d . . . . .
H10N H 0.446142 -0.080049 0.494442 0.046 Uiso 1 1 calc R U . . .
C11N C 0.3919(6) -0.0177(7) 0.4180(2) 0.0375(10) Uani 1 1 d . . . . .
H11N H 0.276945 -0.052530 0.417812 0.045 Uiso 1 1 calc R U . . .
C12N C 0.4636(6) 0.0475(6) 0.37465(18) 0.0311(9) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C2 1.228(5) . ?
O3 N3 1.233(4) . ?
O4 N3 1.229(4) . ?
O5 N5 1.236(4) . ?
O6 N5 1.211(5) . ?
N1 C6 1.339(5) . ?
N1 C2 1.387(5) . ?
N1 H1 0.82(5) . ?
N3 C3 1.452(5) . ?
N5 C5 1.459(5) . ?
C2 C3 1.456(5) . ?
C3 C4 1.362(5) . ?
C4 C5 1.386(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.376(5) . ?
C6 H6 0.9500 . ?
O2' C2' 1.236(5) . ?
O3' N3' 1.232(4) . ?
O4' N3' 1.230(4) . ?
O5' N5' 1.238(5) . ?
O6' N5' 1.217(5) . ?
N1' C6' 1.347(5) . ?
N1' C2' 1.395(5) . ?
N1' H1' 0.94(5) . ?
N3' C3' 1.452(5) . ?
N5' C5' 1.457(5) . ?
C2' C3' 1.447(5) . ?
C3' C4' 1.362(5) . ?
C4' C5' 1.384(5) . ?
C4' H4' 0.9500 . ?
C5' C6' 1.370(5) . ?
C6' H6' 0.9500 . ?
C1M C2M 1.335(7) . ?
C1M C12M 1.476(7) . ?
C1M H1M 0.9500 . ?
C2M C3M 1.472(6) . ?
C2M H2M 0.9500 . ?
C3M C4M 1.387(6) . ?
C3M C8M 1.397(6) . ?
C4M C5M 1.420(7) . ?
C4M H4M 0.9500 . ?
C5M C6M 1.372(7) . ?
C5M H5M 0.9500 . ?
C6M C7M 1.434(6) . ?
C6M H6M 0.9500 . ?
C7M C8M 1.379(5) . ?
C7M C9M 1.418(6) . ?
C8M C12M 1.426(6) . ?
C9M C10M 1.368(7) . ?
C9M H9M 0.9500 . ?
C10M C11M 1.413(7) . ?
C10M H10M 0.9500 . ?
C11M C12M 1.369(7) . ?
C11M H11M 0.9500 . ?
C1N C2N 1.345(8) . ?
C1N C12N 1.480(6) . ?
C1N H1N 0.9500 . ?
C2N C3N 1.458(7) . ?
C2N H2N 0.9500 . ?
C3N C4N 1.357(7) . ?
C3N C8N 1.414(6) . ?
C4N C5N 1.412(7) . ?
C4N H4N 0.9500 . ?
C5N C6N 1.384(7) . ?
C5N H5N 0.9500 . ?
C6N C7N 1.410(6) . ?
C6N H6N 0.9500 . ?
C7N C8N 1.396(6) . ?
C7N C9N 1.439(6) . ?
C8N C12N 1.406(6) . ?
C9N C10N 1.349(7) . ?
C9N H9N 0.9500 . ?
C10N C11N 1.437(7) . ?
C10N H10N 0.9500 . ?
C11N C12N 1.358(7) . ?
C11N H11N 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
C6 N1 C2 126.4(3) . . ?
C6 N1 H1 114(4) . . ?
C2 N1 H1 119(4) . . ?
O4 N3 O3 123.2(3) . . ?
O4 N3 C3 117.9(3) . . ?
O3 N3 C3 118.9(3) . . ?
O6 N5 O5 124.7(3) . . ?
O6 N5 C5 118.6(3) . . ?
O5 N5 C5 116.8(3) . . ?
O2 C2 N1 119.1(3) . . ?
O2 C2 C3 128.1(4) . . ?
N1 C2 C3 112.8(3) . . ?
C4 C3 N3 117.5(3) . . ?
C4 C3 C2 122.1(4) . . ?
N3 C3 C2 120.3(3) . . ?
C3 C4 C5 119.4(4) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 N5 117.8(3) . . ?
C4 C5 N5 121.3(3) . . ?
N1 C6 C5 118.3(4) . . ?
N1 C6 H6 120.9 . . ?
C5 C6 H6 120.9 . . ?
C6' N1' C2' 126.1(3) . . ?
C6' N1' H1' 118(3) . . ?
C2' N1' H1' 115(3) . . ?
O4' N3' O3' 123.3(3) . . ?
O4' N3' C3' 117.6(3) . . ?
O3' N3' C3' 119.1(3) . . ?
O6' N5' O5' 124.5(3) . . ?
O6' N5' C5' 119.1(3) . . ?
O5' N5' C5' 116.3(3) . . ?
O2' C2' N1' 119.0(3) . . ?
O2' C2' C3' 128.4(4) . . ?
N1' C2' C3' 112.6(3) . . ?
C4' C3' C2' 122.8(3) . . ?
C4' C3' N3' 117.3(3) . . ?
C2' C3' N3' 120.0(3) . . ?
C3' C4' C5' 119.0(3) . . ?
C3' C4' H4' 120.5 . . ?
C5' C4' H4' 120.5 . . ?
C6' C5' C4' 121.4(3) . . ?
C6' C5' N5' 118.0(3) . . ?
C4' C5' N5' 120.6(3) . . ?
N1' C6' C5' 118.1(4) . . ?
N1' C6' H6' 121.0 . . ?
C5' C6' H6' 121.0 . . ?
C2M C1M C12M 109.9(4) . . ?
C2M C1M H1M 125.1 . . ?
C12M C1M H1M 125.1 . . ?
C1M C2M C3M 108.7(4) . . ?
C1M C2M H2M 125.6 . . ?
C3M C2M H2M 125.6 . . ?
C4M C3M C8M 117.8(4) . . ?
C4M C3M C2M 135.6(4) . . ?
C8M C3M C2M 106.6(4) . . ?
C3M C4M C5M 117.6(4) . . ?
C3M C4M H4M 121.2 . . ?
C5M C4M H4M 121.2 . . ?
C6M C5M C4M 123.5(4) . . ?
C6M C5M H5M 118.2 . . ?
C4M C5M H5M 118.2 . . ?
C5M C6M C7M 119.6(4) . . ?
C5M C6M H6M 120.2 . . ?
C7M C6M H6M 120.2 . . ?
C8M C7M C9M 117.6(4) . . ?
C8M C7M C6M 114.9(4) . . ?
C9M C7M C6M 127.4(4) . . ?
C7M C8M C3M 126.5(4) . . ?
C7M C8M C12M 123.7(4) . . ?
C3M C8M C12M 109.8(4) . . ?
C10M C9M C7M 118.9(4) . . ?
C10M C9M H9M 120.5 . . ?
C7M C9M H9M 120.5 . . ?
C9M C10M C11M 123.1(4) . . ?
C9M C10M H10M 118.5 . . ?
C11M C10M H10M 118.5 . . ?
C12M C11M C10M 119.2(4) . . ?
C12M C11M H11M 120.4 . . ?
C10M C11M H11M 120.4 . . ?
C11M C12M C8M 117.6(4) . . ?
C11M C12M C1M 137.4(4) . . ?
C8M C12M C1M 105.0(4) . . ?
C2N C1N C12N 108.4(4) . . ?
C2N C1N H1N 125.8 . . ?
C12N C1N H1N 125.8 . . ?
C1N C2N C3N 109.8(4) . . ?
C1N C2N H2N 125.1 . . ?
C3N C2N H2N 125.1 . . ?
C4N C3N C8N 117.6(4) . . ?
C4N C3N C2N 136.3(4) . . ?
C8N C3N C2N 106.1(4) . . ?
C3N C4N C5N 120.1(4) . . ?
C3N C4N H4N 119.9 . . ?
C5N C4N H4N 119.9 . . ?
C6N C5N C4N 121.7(4) . . ?
C6N C5N H5N 119.1 . . ?
C4N C5N H5N 119.1 . . ?
C5N C6N C7N 119.8(4) . . ?
C5N C6N H6N 120.1 . . ?
C7N C6N H6N 120.1 . . ?
C8N C7N C6N 116.4(4) . . ?
C8N C7N C9N 114.7(4) . . ?
C6N C7N C9N 128.8(4) . . ?
C7N C8N C12N 126.0(4) . . ?
C7N C8N C3N 124.3(4) . . ?
C12N C8N C3N 109.7(4) . . ?
C10N C9N C7N 119.5(5) . . ?
C10N C9N H9N 120.3 . . ?
C7N C9N H9N 120.3 . . ?
C9N C10N C11N 124.1(5) . . ?
C9N C10N H10N 117.9 . . ?
C11N C10N H10N 117.9 . . ?
C12N C11N C10N 117.8(5) . . ?
C12N C11N H11N 121.1 . . ?
C10N C11N H11N 121.1 . . ?
C11N C12N C8N 118.0(4) . . ?
C11N C12N C1N 135.9(5) . . ?
C8N C12N C1N 106.1(4) . . ?

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 O2 -177.1(4) . . . . ?
C6 N1 C2 C3 2.7(5) . . . . ?
O4 N3 C3 C4 -7.9(5) . . . . ?
O3 N3 C3 C4 172.2(3) . . . . ?
O4 N3 C3 C2 171.7(3) . . . . ?
O3 N3 C3 C2 -8.3(5) . . . . ?
O2 C2 C3 C4 176.7(4) . . . . ?
N1 C2 C3 C4 -3.0(5) . . . . ?
O2 C2 C3 N3 -2.8(6) . . . . ?
N1 C2 C3 N3 177.5(3) . . . . ?
N3 C3 C4 C5 -179.1(3) . . . . ?
C2 C3 C4 C5 1.4(5) . . . . ?
C3 C4 C5 C6 1.0(5) . . . . ?
C3 C4 C5 N5 179.9(3) . . . . ?
O6 N5 C5 C6 4.9(5) . . . . ?
O5 N5 C5 C6 -175.7(3) . . . . ?
O6 N5 C5 C4 -174.0(3) . . . . ?
O5 N5 C5 C4 5.5(5) . . . . ?
C2 N1 C6 C5 -0.6(5) . . . . ?
C4 C5 C6 N1 -1.4(5) . . . . ?
N5 C5 C6 N1 179.7(3) . . . . ?
C6' N1' C2' O2' -174.6(4) . . . . ?
C6' N1' C2' C3' 3.6(5) . . . . ?
O2' C2' C3' C4' 174.1(4) . . . . ?
N1' C2' C3' C4' -3.9(5) . . . . ?
O2' C2' C3' N3' -6.4(6) . . . . ?
N1' C2' C3' N3' 175.6(3) . . . . ?
O4' N3' C3' C4' -14.6(5) . . . . ?
O3' N3' C3' C4' 164.4(4) . . . . ?
O4' N3' C3' C2' 165.9(3) . . . . ?
O3' N3' C3' C2' -15.1(5) . . . . ?
C2' C3' C4' C5' 1.9(5) . . . . ?
N3' C3' C4' C5' -177.6(3) . . . . ?
C3' C4' C5' C6' 0.9(5) . . . . ?
C3' C4' C5' N5' 178.7(3) . . . . ?
O6' N5' C5' C6' 4.2(5) . . . . ?
O5' N5' C5' C6' -175.2(4) . . . . ?
O6' N5' C5' C4' -173.6(3) . . . . ?
O5' N5' C5' C4' 6.9(5) . . . . ?
C2' N1' C6' C5' -1.2(6) . . . . ?
C4' C5' C6' N1' -1.3(6) . . . . ?
N5' C5' C6' N1' -179.2(3) . . . . ?
C12M C1M C2M C3M 0.9(5) . . . . ?
C1M C2M C3M C4M 177.1(5) . . . . ?
C1M C2M C3M C8M -0.9(5) . . . . ?
C8M C3M C4M C5M 0.7(6) . . . . ?
C2M C3M C4M C5M -177.1(5) . . . . ?
C3M C4M C5M C6M -0.1(6) . . . . ?
C4M C5M C6M C7M -1.4(6) . . . . ?
C5M C6M C7M C8M 2.3(6) . . . . ?
C5M C6M C7M C9M 179.3(4) . . . . ?
C9M C7M C8M C3M -179.2(4) . . . . ?
C6M C7M C8M C3M -1.8(6) . . . . ?
C9M C7M C8M C12M -1.1(5) . . . . ?
C6M C7M C8M C12M 176.2(4) . . . . ?
C4M C3M C8M C7M 0.3(6) . . . . ?
C2M C3M C8M C7M 178.7(4) . . . . ?
C4M C3M C8M C12M -178.0(4) . . . . ?
C2M C3M C8M C12M 0.4(4) . . . . ?
C8M C7M C9M C10M 0.2(5) . . . . ?
C6M C7M C9M C10M -176.8(4) . . . . ?
C7M C9M C10M C11M 1.0(6) . . . . ?
C9M C10M C11M C12M -1.3(6) . . . . ?
C10M C11M C12M C8M 0.4(6) . . . . ?
C10M C11M C12M C1M 179.0(4) . . . . ?
C7M C8M C12M C11M 0.8(6) . . . . ?
C3M C8M C12M C11M 179.2(4) . . . . ?
C7M C8M C12M C1M -178.2(4) . . . . ?
C3M C8M C12M C1M 0.1(4) . . . . ?
C2M C1M C12M C11M -179.4(5) . . . . ?
C2M C1M C12M C8M -0.7(5) . . . . ?
C12N C1N C2N C3N -0.6(5) . . . . ?
C1N C2N C3N C4N 177.5(5) . . . . ?
C1N C2N C3N C8N -0.2(5) . . . . ?
C8N C3N C4N C5N -1.2(6) . . . . ?
C2N C3N C4N C5N -178.7(5) . . . . ?
C3N C4N C5N C6N 1.6(7) . . . . ?
C4N C5N C6N C7N -0.2(7) . . . . ?
C5N C6N C7N C8N -1.5(6) . . . . ?
C5N C6N C7N C9N 175.9(4) . . . . ?
C6N C7N C8N C12N 177.9(4) . . . . ?
C9N C7N C8N C12N 0.2(6) . . . . ?
C6N C7N C8N C3N 1.9(6) . . . . ?
C9N C7N C8N C3N -175.8(4) . . . . ?
C4N C3N C8N C7N -0.6(6) . . . . ?
C2N C3N C8N C7N 177.6(4) . . . . ?
C4N C3N C8N C12N -177.1(4) . . . . ?
C2N C3N C8N C12N 1.1(5) . . . . ?
C8N C7N C9N C10N 0.1(6) . . . . ?
C6N C7N C9N C10N -177.3(4) . . . . ?
C7N C9N C10N C11N -0.7(7) . . . . ?
C9N C10N C11N C12N 1.2(7) . . . . ?
C10N C11N C12N C8N -0.9(6) . . . . ?
C10N C11N C12N C1N 176.6(5) . . . . ?
C7N C8N C12N C11N 0.2(6) . . . . ?
C3N C8N C12N C11N 176.7(4) . . . . ?
C7N C8N C12N C1N -177.9(4) . . . . ?
C3N C8N C12N C1N -1.4(4) . . . . ?
C2N C1N C12N C11N -176.3(5) . . . . ?
C2N C1N C12N C8N 1.3(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
N1 H1 O2' 0.82(5) 2.05(6) 2.757(4) 144(5) . yes
N1 H1 O3' 0.82(5) 2.54(5) 3.194(4) 138(5) . yes
N1' H1' O2 0.94(5) 1.96(5) 2.723(4) 138(4) 1_655 yes
N1' H1' O3 0.94(5) 2.48(5) 3.315(4) 148(4) 1_655 yes

_refine_diff_density_max         0.198
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.046




# start Validation Reply Form
_vrf_PLAT029_35dnp2o-acnft       
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.949 Why?
RESPONSE: The crystal was a two-component twin, and we were unable to measure
all reflecions with our setup. However, the fraction is still high and the
model is unambiguous.
;
# end Validation Reply Form

####################################################################### 
# 
# 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_35dnp2o-tph
_database_code_depnum_ccdc_archive 'CCDC 2123843'
loop_
_audit_author_name
_audit_author_address
'Ivan Fedyanin'
;Institute of Organoelement Compounds of Russian Academy of Sciences (INEOS RAS)
Russia
;
_audit_update_record             
;
2021-11-23 deposited with the CCDC.	2022-02-24 downloaded from the CCDC.
;

_publ_contact_name               'Fedyanin, Ivan V.'
_publ_contact_email              octy@xrlab.ineos.ac.ru

_audit_creation_method           'Modified SHELXL output'
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H12, C5 H3 N3 O5'
_chemical_formula_sum            'C23 H15 N3 O5'
_chemical_formula_weight         413.38

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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   7.6442(3)
_cell_length_b                   8.6092(3)
_cell_length_c                   27.0462(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1779.92(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9900
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      31.64

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.340
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.111
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.723
_exptl_absorpt_correction_T_max  0.747
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX DUO diffractometer'
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'ο scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44112
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -43
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.483
_diffrn_reflns_theta_max         34.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7853
_reflns_number_gt                6771
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.775
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0500P)²+0.4000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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_abs_structure_details 
;
 Flack x determined using 2609 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         7853
_refine_ls_number_parameters     284
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0516
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1023
_refine_ls_wR_factor_gt          0.0962
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_restrained_S_all      0.996
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.55823(18) 0.63401(13) 0.25283(4) 0.0241(3) Uani 1 1 d . . . . .
O3 O 0.67961(17) 0.38712(12) 0.20099(4) 0.0204(2) Uani 1 1 d . . . . .
O4 O 0.87388(18) 0.44544(15) 0.14623(5) 0.0275(3) Uani 1 1 d . . . . .
O5 O 0.80795(17) 0.92247(14) 0.05590(4) 0.0230(2) Uani 1 1 d . . . . .
O6 O 0.67345(19) 1.11524(13) 0.09070(5) 0.0246(3) Uani 1 1 d . . . . .
N1 N 0.55651(18) 0.85813(14) 0.20946(5) 0.0156(2) Uani 1 1 d . . . . .
H1 H 0.505(3) 0.904(3) 0.2348(9) 0.027(6) Uiso 1 1 d . . . . .
N3 N 0.75260(18) 0.47982(14) 0.17354(5) 0.0162(2) Uani 1 1 d . . . . .
N5 N 0.72352(18) 0.98006(15) 0.08962(5) 0.0163(2) Uani 1 1 d . . . . .
C2 C 0.5987(2) 0.70116(16) 0.21488(6) 0.0156(3) Uani 1 1 d . . . . .
C3 C 0.69362(19) 0.64065(15) 0.17279(5) 0.0133(2) Uani 1 1 d . . . . .
C4 C 0.73493(19) 0.72766(15) 0.13240(5) 0.0137(2) Uani 1 1 d . . . . .
H4 H 0.798589 0.684051 0.105618 0.016 Uiso 1 1 calc R U . . .
C5 C 0.6813(2) 0.88257(15) 0.13138(5) 0.0134(2) Uani 1 1 d . . . . .
C6 C 0.5936(2) 0.94587(16) 0.17013(5) 0.0150(2) Uani 1 1 d . . . . .
H6 H 0.558932 1.051800 0.169256 0.018 Uiso 1 1 calc R U . . .
C1T C 0.2769(2) 0.54502(17) 0.14715(6) 0.0197(3) Uani 1 1 d . . . . .
H1T H 0.220382 0.532506 0.178172 0.024 Uiso 1 1 calc R U . . .
C2T C 0.3657(2) 0.42152(17) 0.12686(7) 0.0226(3) Uani 1 1 d . . . . .
H2T H 0.368696 0.324619 0.143635 0.027 Uiso 1 1 calc R U . . .
C3T C 0.4507(2) 0.43847(17) 0.08196(7) 0.0225(3) Uani 1 1 d . . . . .
H3T H 0.514112 0.353890 0.068275 0.027 Uiso 1 1 calc R U . . .
C4T C 0.4431(2) 0.57778(17) 0.05720(6) 0.0192(3) Uani 1 1 d . . . . .
H4T H 0.501014 0.588010 0.026287 0.023 Uiso 1 1 calc R U . . .
C5T C 0.3513(2) 0.70564(16) 0.07674(6) 0.0153(3) Uani 1 1 d . . . . .
C6T C 0.3424(2) 0.85317(16) 0.05004(6) 0.0158(3) Uani 1 1 d . . . . .
C7T C 0.4313(2) 0.87491(19) 0.00512(6) 0.0206(3) Uani 1 1 d . . . . .
H7T H 0.499262 0.792383 -0.008088 0.025 Uiso 1 1 calc R U . . .
C8T C 0.4218(3) 1.0135(2) -0.02017(7) 0.0255(3) Uani 1 1 d . . . . .
H8T H 0.484757 1.026684 -0.050152 0.031 Uiso 1 1 calc R U . . .
C9T C 0.3200(3) 1.13383(19) -0.00175(7) 0.0258(3) Uani 1 1 d . . . . .
H9T H 0.310792 1.228667 -0.019516 0.031 Uiso 1 1 calc R U . . .
C10T C 0.2327(2) 1.11550(18) 0.04212(6) 0.0220(3) Uani 1 1 d . . . . .
H10T H 0.162619 1.198301 0.054220 0.026 Uiso 1 1 calc R U . . .
C11T C 0.2442(2) 0.97725(16) 0.06977(6) 0.0160(3) Uani 1 1 d . . . . .
C12T C 0.1638(2) 0.96266(16) 0.11837(6) 0.0158(2) Uani 1 1 d . . . . .
C13T C 0.0748(2) 1.08795(18) 0.14070(7) 0.0208(3) Uani 1 1 d . . . . .
H13T H 0.063156 1.182811 0.123063 0.025 Uiso 1 1 calc R U . . .
C14T C 0.0048(2) 1.0762(2) 0.18723(7) 0.0246(3) Uani 1 1 d . . . . .
H14T H -0.056123 1.161721 0.201226 0.030 Uiso 1 1 calc R U . . .
C15T C 0.0229(2) 0.9389(2) 0.21395(7) 0.0245(3) Uani 1 1 d . . . . .
H15T H -0.022820 0.931231 0.246517 0.029 Uiso 1 1 calc R U . . .
C16T C 0.1074(2) 0.8147(2) 0.19282(6) 0.0210(3) Uani 1 1 d . . . . .
H16T H 0.118304 0.721054 0.211134 0.025 Uiso 1 1 calc R U . . .
C17T C 0.1781(2) 0.82203(16) 0.14502(6) 0.0158(2) Uani 1 1 d . . . . .
C18T C 0.26811(19) 0.68971(16) 0.12291(6) 0.0152(2) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C2 1.2179(18) . ?
O3 N3 1.2245(16) . ?
O4 N3 1.2217(18) . ?
O5 N5 1.2223(17) . ?
O6 N5 1.2254(17) . ?
N1 C6 1.3351(19) . ?
N1 C2 1.3970(18) . ?
N1 H1 0.89(2) . ?
N3 C3 1.4563(18) . ?
N5 C5 1.4435(18) . ?
C2 C3 1.447(2) . ?
C3 C4 1.362(2) . ?
C4 C5 1.3955(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.358(2) . ?
C6 H6 0.9500 . ?
C1T C2T 1.375(2) . ?
C1T C18T 1.409(2) . ?
C1T H1T 0.9500 . ?
C2T C3T 1.385(3) . ?
C2T H2T 0.9500 . ?
C3T C4T 1.375(2) . ?
C3T H3T 0.9500 . ?
C4T C5T 1.409(2) . ?
C4T H4T 0.9500 . ?
C5T C18T 1.408(2) . ?
C5T C6T 1.463(2) . ?
C6T C7T 1.404(2) . ?
C6T C11T 1.411(2) . ?
C7T C8T 1.377(2) . ?
C7T H7T 0.9500 . ?
C8T C9T 1.388(3) . ?
C8T H8T 0.9500 . ?
C9T C10T 1.370(3) . ?
C9T H9T 0.9500 . ?
C10T C11T 1.408(2) . ?
C10T H10T 0.9500 . ?
C11T C12T 1.456(2) . ?
C12T C13T 1.411(2) . ?
C12T C17T 1.413(2) . ?
C13T C14T 1.371(3) . ?
C13T H13T 0.9500 . ?
C14T C15T 1.392(3) . ?
C14T H14T 0.9500 . ?
C15T C16T 1.374(2) . ?
C15T H15T 0.9500 . ?
C16T C17T 1.402(2) . ?
C16T H16T 0.9500 . ?
C17T C18T 1.459(2) . ?

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
C6 N1 C2 125.59(13) . . ?
C6 N1 H1 117.5(15) . . ?
C2 N1 H1 116.9(15) . . ?
O4 N3 O3 123.67(13) . . ?
O4 N3 C3 117.19(13) . . ?
O3 N3 C3 119.14(13) . . ?
O5 N5 O6 124.60(13) . . ?
O5 N5 C5 117.77(12) . . ?
O6 N5 C5 117.64(13) . . ?
O2 C2 N1 119.28(14) . . ?
O2 C2 C3 128.27(13) . . ?
N1 C2 C3 112.42(12) . . ?
C4 C3 C2 123.32(12) . . ?
C4 C3 N3 117.54(12) . . ?
C2 C3 N3 119.12(12) . . ?
C3 C4 C5 118.26(13) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
C6 C5 C4 120.87(13) . . ?
C6 C5 N5 118.73(12) . . ?
C4 C5 N5 120.37(13) . . ?
N1 C6 C5 119.51(13) . . ?
N1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C2T C1T C18T 121.42(16) . . ?
C2T C1T H1T 119.3 . . ?
C18T C1T H1T 119.3 . . ?
C1T C2T C3T 119.99(15) . . ?
C1T C2T H2T 120.0 . . ?
C3T C2T H2T 120.0 . . ?
C4T C3T C2T 119.96(15) . . ?
C4T C3T H3T 120.0 . . ?
C2T C3T H3T 120.0 . . ?
C3T C4T C5T 121.32(16) . . ?
C3T C4T H4T 119.3 . . ?
C5T C4T H4T 119.3 . . ?
C18T C5T C4T 118.80(13) . . ?
C18T C5T C6T 120.11(13) . . ?
C4T C5T C6T 121.09(14) . . ?
C7T C6T C11T 118.94(13) . . ?
C7T C6T C5T 121.37(14) . . ?
C11T C6T C5T 119.69(14) . . ?
C8T C7T C6T 121.31(16) . . ?
C8T C7T H7T 119.3 . . ?
C6T C7T H7T 119.3 . . ?
C7T C8T C9T 119.87(17) . . ?
C7T C8T H8T 120.1 . . ?
C9T C8T H8T 120.1 . . ?
C10T C9T C8T 119.84(15) . . ?
C10T C9T H9T 120.1 . . ?
C8T C9T H9T 120.1 . . ?
C9T C10T C11T 121.80(16) . . ?
C9T C10T H10T 119.1 . . ?
C11T C10T H10T 119.1 . . ?
C10T C11T C6T 118.18(15) . . ?
C10T C11T C12T 121.72(14) . . ?
C6T C11T C12T 120.05(13) . . ?
C13T C12T C17T 118.28(14) . . ?
C13T C12T C11T 121.59(13) . . ?
C17T C12T C11T 120.11(13) . . ?
C14T C13T C12T 121.64(15) . . ?
C14T C13T H13T 119.2 . . ?
C12T C13T H13T 119.2 . . ?
C13T C14T C15T 120.02(16) . . ?
C13T C14T H14T 120.0 . . ?
C15T C14T H14T 120.0 . . ?
C16T C15T C14T 119.44(16) . . ?
C16T C15T H15T 120.3 . . ?
C14T C15T H15T 120.3 . . ?
C15T C16T C17T 121.97(16) . . ?
C15T C16T H16T 119.0 . . ?
C17T C16T H16T 119.0 . . ?
C16T C17T C12T 118.62(14) . . ?
C16T C17T C18T 121.62(14) . . ?
C12T C17T C18T 119.75(14) . . ?
C5T C18T C1T 118.49(13) . . ?
C5T C18T C17T 120.03(13) . . ?
C1T C18T C17T 121.47(14) . . ?

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 O2 179.61(16) . . . . ?
C6 N1 C2 C3 1.4(2) . . . . ?
O2 C2 C3 C4 -178.66(16) . . . . ?
N1 C2 C3 C4 -0.6(2) . . . . ?
O2 C2 C3 N3 -0.2(2) . . . . ?
N1 C2 C3 N3 177.86(13) . . . . ?
O4 N3 C3 C4 20.5(2) . . . . ?
O3 N3 C3 C4 -159.51(14) . . . . ?
O4 N3 C3 C2 -158.10(15) . . . . ?
O3 N3 C3 C2 21.9(2) . . . . ?
C2 C3 C4 C5 -0.7(2) . . . . ?
N3 C3 C4 C5 -179.20(13) . . . . ?
C3 C4 C5 C6 1.4(2) . . . . ?
C3 C4 C5 N5 179.33(13) . . . . ?
O5 N5 C5 C6 177.42(14) . . . . ?
O6 N5 C5 C6 -1.9(2) . . . . ?
O5 N5 C5 C4 -0.5(2) . . . . ?
O6 N5 C5 C4 -179.88(14) . . . . ?
C2 N1 C6 C5 -0.7(2) . . . . ?
C4 C5 C6 N1 -0.8(2) . . . . ?
N5 C5 C6 N1 -178.71(13) . . . . ?
C18T C1T C2T C3T 0.8(3) . . . . ?
C1T C2T C3T C4T -1.4(3) . . . . ?
C2T C3T C4T C5T 0.5(3) . . . . ?
C3T C4T C5T C18T 0.9(2) . . . . ?
C3T C4T C5T C6T -179.48(15) . . . . ?
C18T C5T C6T C7T 176.80(14) . . . . ?
C4T C5T C6T C7T -2.8(2) . . . . ?
C18T C5T C6T C11T -2.6(2) . . . . ?
C4T C5T C6T C11T 177.74(14) . . . . ?
C11T C6T C7T C8T -1.1(2) . . . . ?
C5T C6T C7T C8T 179.50(15) . . . . ?
C6T C7T C8T C9T -1.3(3) . . . . ?
C7T C8T C9T C10T 1.6(3) . . . . ?
C8T C9T C10T C11T 0.6(3) . . . . ?
C9T C10T C11T C6T -2.9(2) . . . . ?
C9T C10T C11T C12T 174.62(16) . . . . ?
C7T C6T C11T C10T 3.1(2) . . . . ?
C5T C6T C11T C10T -177.47(14) . . . . ?
C7T C6T C11T C12T -174.48(14) . . . . ?
C5T C6T C11T C12T 5.0(2) . . . . ?
C10T C11T C12T C13T -1.9(2) . . . . ?
C6T C11T C12T C13T 175.61(14) . . . . ?
C10T C11T C12T C17T 179.98(15) . . . . ?
C6T C11T C12T C17T -2.6(2) . . . . ?
C17T C12T C13T C14T 0.7(2) . . . . ?
C11T C12T C13T C14T -177.51(15) . . . . ?
C12T C13T C14T C15T 1.0(3) . . . . ?
C13T C14T C15T C16T -1.6(3) . . . . ?
C14T C15T C16T C17T 0.6(3) . . . . ?
C15T C16T C17T C12T 1.1(2) . . . . ?
C15T C16T C17T C18T 179.80(15) . . . . ?
C13T C12T C17T C16T -1.7(2) . . . . ?
C11T C12T C17T C16T 176.55(14) . . . . ?
C13T C12T C17T C18T 179.56(14) . . . . ?
C11T C12T C17T C18T -2.2(2) . . . . ?
C4T C5T C18T C1T -1.4(2) . . . . ?
C6T C5T C18T C1T 178.94(14) . . . . ?
C4T C5T C18T C17T 177.50(14) . . . . ?
C6T C5T C18T C17T -2.1(2) . . . . ?
C2T C1T C18T C5T 0.6(2) . . . . ?
C2T C1T C18T C17T -178.31(15) . . . . ?
C16T C17T C18T C5T -174.19(14) . . . . ?
C12T C17T C18T C5T 4.5(2) . . . . ?
C16T C17T C18T C1T 4.7(2) . . . . ?
C12T C17T C18T C1T -176.54(14) . . . . ?

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
N1 H1 O2 0.89(2) 2.07(2) 2.7297(17) 131(2) 3_655 yes
N1 H1 O3 0.89(2) 2.24(2) 3.0310(18) 149(2) 3_655 yes

_refine_diff_density_max         0.408
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.055




####################################################################### 
# 
# 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_35dnp2o-prl
_database_code_depnum_ccdc_archive 'CCDC 2123847'
loop_
_audit_author_name
_audit_author_address
'Ivan Fedyanin'
;Institute of Organoelement Compounds of Russian Academy of Sciences (INEOS RAS)
Russia
;
_audit_update_record             
;
2021-11-23 deposited with the CCDC.	2022-02-24 downloaded from the CCDC.
;

_publ_contact_name               'Fedyanin, Ivan V.'
_publ_contact_email              octy@xrlab.ineos.ac.ru

_audit_creation_method           'Modified SHELXL output'
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H12, 2(C5 H3 N3 O5)'
_chemical_formula_sum            'C30 H18 N6 O10'
_chemical_formula_weight         622.50

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                   13.6099(8)
_cell_length_b                   8.6026(5)
_cell_length_c                   21.6767(13)
_cell_angle_alpha                90
_cell_angle_beta                 90.440(3)
_cell_angle_gamma                90
_cell_volume                     2537.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9682
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      72.68

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.629
_exptl_crystal_F_000             1280
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    1.070
_shelx_estimated_absorpt_T_min   0.815
_shelx_estimated_absorpt_T_max   0.939
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.687
_exptl_absorpt_correction_T_max  0.864
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX DUO diffractometer'
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'ο and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            57378
_diffrn_reflns_av_unetI/netI     0.0236
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.247
_diffrn_reflns_theta_max         72.811
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5019
_reflns_number_gt                4734
_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 (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0431P)²+5.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         5019
_refine_ls_number_parameters     423
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0546
_refine_ls_wR_factor_ref         0.1398
_refine_ls_wR_factor_gt          0.1385
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.52415(13) 0.2983(2) 0.23698(8) 0.0294(4) Uani 1 1 d . . . . .
O3 O 0.48207(14) 0.0487(2) 0.16394(8) 0.0302(4) Uani 1 1 d . . . . .
O4 O 0.47350(14) 0.0963(2) 0.06602(8) 0.0319(4) Uani 1 1 d . . . . .
O5 O 0.37406(15) 0.5933(2) -0.00629(8) 0.0341(4) Uani 1 1 d . . . . .
O6 O 0.36284(14) 0.7887(2) 0.05680(8) 0.0319(4) Uani 1 1 d . . . . .
N1 N 0.46962(14) 0.5267(2) 0.19687(9) 0.0213(4) Uani 1 1 d . . . . .
H1 H 0.483(2) 0.563(4) 0.2334(14) 0.027(7) Uiso 1 1 d . . . . .
N3 N 0.47459(15) 0.1380(2) 0.11982(9) 0.0249(4) Uani 1 1 d . . . . .
N5 N 0.38245(15) 0.6524(2) 0.04520(9) 0.0249(4) Uani 1 1 d . . . . .
C2 C 0.48864(17) 0.3669(3) 0.19253(11) 0.0230(5) Uani 1 1 d . . . . .
C3 C 0.46399(17) 0.3052(3) 0.13201(11) 0.0223(5) Uani 1 1 d . . . . .
C4 C 0.43138(17) 0.3956(3) 0.08467(11) 0.0238(5) Uani 1 1 d . . . . .
H4 H 0.418330 0.351489 0.045275 0.029 Uiso 1 1 calc R U . . .
C5 C 0.41736(17) 0.5546(3) 0.09481(10) 0.0224(5) Uani 1 1 d . . . . .
C6 C 0.43622(17) 0.6177(3) 0.15162(11) 0.0233(5) Uani 1 1 d . . . . .
H6 H 0.425612 0.725390 0.158716 0.028 Uiso 1 1 calc R U . . .
O2' O 0.01723(13) 0.25280(19) 0.25513(7) 0.0242(4) Uani 1 1 d . . . . .
O3' O 0.06771(15) 0.0068(2) 0.32624(8) 0.0326(4) Uani 1 1 d . . . . .
O4' O 0.11537(14) 0.0501(2) 0.41955(8) 0.0298(4) Uani 1 1 d . . . . .
O5' O 0.11480(13) 0.5516(2) 0.50698(7) 0.0266(4) Uani 1 1 d . . . . .
O6' O 0.04265(14) 0.74336(19) 0.45977(8) 0.0288(4) Uani 1 1 d . . . . .
N1' N 0.01335(14) 0.4823(2) 0.30549(9) 0.0197(4) Uani 1 1 d . . . . .
H1' H -0.006(2) 0.524(3) 0.2730(13) 0.022(7) Uiso 1 1 d . . . . .
N3' N 0.08365(14) 0.0941(2) 0.36982(9) 0.0216(4) Uani 1 1 d . . . . .
N5' N 0.07360(14) 0.6092(2) 0.46187(9) 0.0209(4) Uani 1 1 d . . . . .
C2' C 0.03080(16) 0.3217(3) 0.30346(10) 0.0193(4) Uani 1 1 d . . . . .
C3' C 0.06376(16) 0.2604(3) 0.36259(10) 0.0190(4) Uani 1 1 d . . . . .
C4' C 0.07851(16) 0.3520(3) 0.41288(10) 0.0195(4) Uani 1 1 d . . . . .
H4' H 0.101494 0.308420 0.450586 0.023 Uiso 1 1 calc R U . . .
C5' C 0.05941(16) 0.5110(3) 0.40833(10) 0.0196(5) Uani 1 1 d . . . . .
C6' C 0.02667(16) 0.5749(3) 0.35433(10) 0.0201(5) Uani 1 1 d . . . . .
H6' H 0.013608 0.683149 0.351518 0.024 Uiso 1 1 calc R U . . .
C1P C 0.24349(16) 0.5762(3) 0.27564(11) 0.0212(5) Uani 1 1 d . . . . .
C2P C 0.23644(18) 0.7206(3) 0.30371(11) 0.0249(5) Uani 1 1 d . . . . .
H2P H 0.213338 0.806786 0.280350 0.030 Uiso 1 1 calc R U . . .
C3P C 0.26266(18) 0.7422(3) 0.36584(12) 0.0273(5) Uani 1 1 d . . . . .
H3P H 0.257937 0.842762 0.383695 0.033 Uiso 1 1 calc R U . . .
C4P C 0.29489(18) 0.6204(3) 0.40091(11) 0.0258(5) Uani 1 1 d . . . . .
H4P H 0.313404 0.636933 0.442745 0.031 Uiso 1 1 calc R U . . .
C5P C 0.30081(16) 0.4693(3) 0.37508(11) 0.0219(5) Uani 1 1 d . . . . .
C6P C 0.32959(18) 0.3408(3) 0.41159(11) 0.0269(5) Uani 1 1 d . . . . .
H6P H 0.348293 0.356249 0.453460 0.032 Uiso 1 1 calc R U . . .
C7P C 0.33069(18) 0.1949(3) 0.38713(12) 0.0270(5) Uani 1 1 d . . . . .
H7P H 0.348456 0.108975 0.412368 0.032 Uiso 1 1 calc R U . . .
C8P C 0.30592(17) 0.1708(3) 0.32525(12) 0.0246(5) Uani 1 1 d . . . . .
H8P H 0.307250 0.068137 0.309173 0.029 Uiso 1 1 calc R U . . .
C9P C 0.27929(16) 0.2930(3) 0.28639(11) 0.0211(5) Uani 1 1 d . . . . .
C10P C 0.27544(16) 0.4469(3) 0.31173(11) 0.0201(5) Uani 1 1 d . . . . .
C11P C 0.21704(16) 0.5511(3) 0.21021(11) 0.0216(5) Uani 1 1 d . . . . .
C12P C 0.18922(17) 0.6723(3) 0.17183(11) 0.0247(5) Uani 1 1 d . . . . .
H12P H 0.187887 0.774825 0.188059 0.030 Uiso 1 1 calc R U . . .
C13P C 0.16290(17) 0.6489(3) 0.10975(12) 0.0268(5) Uani 1 1 d . . . . .
H13P H 0.144436 0.734772 0.084679 0.032 Uiso 1 1 calc R U . . .
C14P C 0.16391(18) 0.5023(3) 0.08549(11) 0.0277(5) Uani 1 1 d . . . . .
H14P H 0.144103 0.486257 0.043848 0.033 Uiso 1 1 calc R U . . .
C15P C 0.19421(17) 0.3741(3) 0.12188(11) 0.0245(5) Uani 1 1 d . . . . .
C16P C 0.20177(18) 0.2237(3) 0.09637(11) 0.0273(5) Uani 1 1 d . . . . .
H16P H 0.183858 0.207281 0.054433 0.033 Uiso 1 1 calc R U . . .
C17P C 0.23448(19) 0.1013(3) 0.13107(12) 0.0284(5) Uani 1 1 d . . . . .
H17P H 0.239926 0.001011 0.113091 0.034 Uiso 1 1 calc R U . . .
C18P C 0.25998(18) 0.1238(3) 0.19317(11) 0.0254(5) Uani 1 1 d . . . . .
H18P H 0.282559 0.037748 0.216779 0.030 Uiso 1 1 calc R U . . .
C19P C 0.25316(16) 0.2681(3) 0.22106(11) 0.0212(5) Uani 1 1 d . . . . .
C20P C 0.22081(16) 0.3975(3) 0.18518(11) 0.0210(5) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C2 1.226(3) . ?
O3 N3 1.230(3) . ?
O4 N3 1.220(3) . ?
O5 N5 1.231(3) . ?
O6 N5 1.229(3) . ?
N1 C6 1.332(3) . ?
N1 C2 1.403(3) . ?
N1 H1 0.87(3) . ?
N3 C3 1.470(3) . ?
N5 C5 1.443(3) . ?
C2 C3 1.452(3) . ?
C3 C4 1.360(3) . ?
C4 C5 1.398(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.369(3) . ?
C6 H6 0.9500 . ?
O2' C2' 1.217(3) . ?
O3' N3' 1.225(3) . ?
O4' N3' 1.218(3) . ?
O5' N5' 1.228(3) . ?
O6' N5' 1.229(3) . ?
N1' C6' 1.336(3) . ?
N1' C2' 1.402(3) . ?
N1' H1' 0.83(3) . ?
N3' C3' 1.464(3) . ?
N5' C5' 1.447(3) . ?
C2' C3' 1.454(3) . ?
C3' C4' 1.359(3) . ?
C4' C5' 1.396(3) . ?
C4' H4' 0.9500 . ?
C5' C6' 1.365(3) . ?
C6' H6' 0.9500 . ?
C1P C2P 1.387(3) . ?
C1P C10P 1.426(3) . ?
C1P C11P 1.477(3) . ?
C2P C3P 1.403(4) . ?
C2P H2P 0.9500 . ?
C3P C4P 1.365(4) . ?
C3P H3P 0.9500 . ?
C4P C5P 1.418(3) . ?
C4P H4P 0.9500 . ?
C5P C6P 1.413(3) . ?
C5P C10P 1.426(3) . ?
C6P C7P 1.362(4) . ?
C6P H6P 0.9500 . ?
C7P C8P 1.396(4) . ?
C7P H7P 0.9500 . ?
C8P C9P 1.393(3) . ?
C8P H8P 0.9500 . ?
C9P C10P 1.434(3) . ?
C9P C19P 1.473(3) . ?
C11P C12P 1.385(3) . ?
C11P C20P 1.430(3) . ?
C12P C13P 1.404(4) . ?
C12P H12P 0.9500 . ?
C13P C14P 1.367(4) . ?
C13P H13P 0.9500 . ?
C14P C15P 1.415(4) . ?
C14P H14P 0.9500 . ?
C15P C16P 1.411(4) . ?
C15P C20P 1.431(3) . ?
C16P C17P 1.366(4) . ?
C16P H16P 0.9500 . ?
C17P C18P 1.401(4) . ?
C17P H17P 0.9500 . ?
C18P C19P 1.384(3) . ?
C18P H18P 0.9500 . ?
C19P C20P 1.425(3) . ?

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
C6 N1 C2 126.1(2) . . ?
C6 N1 H1 122(2) . . ?
C2 N1 H1 112(2) . . ?
O4 N3 O3 124.1(2) . . ?
O4 N3 C3 117.3(2) . . ?
O3 N3 C3 118.6(2) . . ?
O6 N5 O5 124.1(2) . . ?
O6 N5 C5 118.4(2) . . ?
O5 N5 C5 117.5(2) . . ?
O2 C2 N1 119.4(2) . . ?
O2 C2 C3 128.4(2) . . ?
N1 C2 C3 112.2(2) . . ?
C4 C3 C2 123.0(2) . . ?
C4 C3 N3 117.1(2) . . ?
C2 C3 N3 119.9(2) . . ?
C3 C4 C5 119.0(2) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
C6 C5 C4 120.3(2) . . ?
C6 C5 N5 119.8(2) . . ?
C4 C5 N5 119.9(2) . . ?
N1 C6 C5 119.3(2) . . ?
N1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C6' N1' C2' 126.2(2) . . ?
C6' N1' H1' 117(2) . . ?
C2' N1' H1' 117(2) . . ?
O4' N3' O3' 123.5(2) . . ?
O4' N3' C3' 117.53(19) . . ?
O3' N3' C3' 119.01(19) . . ?
O5' N5' O6' 124.2(2) . . ?
O5' N5' C5' 117.40(19) . . ?
O6' N5' C5' 118.34(19) . . ?
O2' C2' N1' 118.8(2) . . ?
O2' C2' C3' 128.8(2) . . ?
N1' C2' C3' 112.39(19) . . ?
C4' C3' C2' 122.7(2) . . ?
C4' C3' N3' 117.0(2) . . ?
C2' C3' N3' 120.3(2) . . ?
C3' C4' C5' 119.0(2) . . ?
C3' C4' H4' 120.5 . . ?
C5' C4' H4' 120.5 . . ?
C6' C5' C4' 121.0(2) . . ?
C6' C5' N5' 119.6(2) . . ?
C4' C5' N5' 119.5(2) . . ?
N1' C6' C5' 118.7(2) . . ?
N1' C6' H6' 120.6 . . ?
C5' C6' H6' 120.6 . . ?
C2P C1P C10P 118.7(2) . . ?
C2P C1P C11P 122.4(2) . . ?
C10P C1P C11P 118.9(2) . . ?
C1P C2P C3P 121.5(2) . . ?
C1P C2P H2P 119.3 . . ?
C3P C2P H2P 119.3 . . ?
C4P C3P C2P 120.7(2) . . ?
C4P C3P H3P 119.6 . . ?
C2P C3P H3P 119.6 . . ?
C3P C4P C5P 120.2(2) . . ?
C3P C4P H4P 119.9 . . ?
C5P C4P H4P 119.9 . . ?
C6P C5P C4P 120.8(2) . . ?
C6P C5P C10P 119.9(2) . . ?
C4P C5P C10P 119.3(2) . . ?
C7P C6P C5P 120.4(2) . . ?
C7P C6P H6P 119.8 . . ?
C5P C6P H6P 119.8 . . ?
C6P C7P C8P 120.5(2) . . ?
C6P C7P H7P 119.8 . . ?
C8P C7P H7P 119.8 . . ?
C9P C8P C7P 121.9(2) . . ?
C9P C8P H8P 119.0 . . ?
C7P C8P H8P 119.0 . . ?
C8P C9P C10P 118.3(2) . . ?
C8P C9P C19P 122.1(2) . . ?
C10P C9P C19P 119.5(2) . . ?
C1P C10P C5P 119.6(2) . . ?
C1P C10P C9P 121.5(2) . . ?
C5P C10P C9P 118.9(2) . . ?
C12P C11P C20P 118.6(2) . . ?
C12P C11P C1P 122.0(2) . . ?
C20P C11P C1P 119.4(2) . . ?
C11P C12P C13P 122.3(2) . . ?
C11P C12P H12P 118.9 . . ?
C13P C12P H12P 118.9 . . ?
C14P C13P C12P 119.9(2) . . ?
C14P C13P H13P 120.1 . . ?
C12P C13P H13P 120.1 . . ?
C13P C14P C15P 120.5(2) . . ?
C13P C14P H14P 119.7 . . ?
C15P C14P H14P 119.7 . . ?
C16P C15P C14P 121.2(2) . . ?
C16P C15P C20P 119.1(2) . . ?
C14P C15P C20P 119.7(2) . . ?
C17P C16P C15P 121.0(2) . . ?
C17P C16P H16P 119.5 . . ?
C15P C16P H16P 119.5 . . ?
C16P C17P C18P 120.0(2) . . ?
C16P C17P H17P 120.0 . . ?
C18P C17P H17P 120.0 . . ?
C19P C18P C17P 121.8(2) . . ?
C19P C18P H18P 119.1 . . ?
C17P C18P H18P 119.1 . . ?
C18P C19P C20P 118.9(2) . . ?
C18P C19P C9P 122.3(2) . . ?
C20P C19P C9P 118.8(2) . . ?
C19P C20P C11P 121.8(2) . . ?
C19P C20P C15P 119.2(2) . . ?
C11P C20P C15P 119.0(2) . . ?

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 O2 176.3(2) . . . . ?
C6 N1 C2 C3 -2.3(3) . . . . ?
O2 C2 C3 C4 -175.0(2) . . . . ?
N1 C2 C3 C4 3.3(3) . . . . ?
O2 C2 C3 N3 4.5(4) . . . . ?
N1 C2 C3 N3 -177.1(2) . . . . ?
O4 N3 C3 C4 14.8(3) . . . . ?
O3 N3 C3 C4 -163.8(2) . . . . ?
O4 N3 C3 C2 -164.8(2) . . . . ?
O3 N3 C3 C2 16.6(3) . . . . ?
C2 C3 C4 C5 -2.4(4) . . . . ?
N3 C3 C4 C5 178.1(2) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C3 C4 C5 N5 -179.8(2) . . . . ?
O6 N5 C5 C6 -5.9(3) . . . . ?
O5 N5 C5 C6 174.3(2) . . . . ?
O6 N5 C5 C4 173.9(2) . . . . ?
O5 N5 C5 C4 -6.0(3) . . . . ?
C2 N1 C6 C5 0.2(4) . . . . ?
C4 C5 C6 N1 1.1(3) . . . . ?
N5 C5 C6 N1 -179.1(2) . . . . ?
C6' N1' C2' O2' -178.5(2) . . . . ?
C6' N1' C2' C3' 1.7(3) . . . . ?
O2' C2' C3' C4' 178.1(2) . . . . ?
N1' C2' C3' C4' -2.0(3) . . . . ?
O2' C2' C3' N3' -1.2(4) . . . . ?
N1' C2' C3' N3' 178.66(19) . . . . ?
O4' N3' C3' C4' -2.6(3) . . . . ?
O3' N3' C3' C4' 177.3(2) . . . . ?
O4' N3' C3' C2' 176.7(2) . . . . ?
O3' N3' C3' C2' -3.4(3) . . . . ?
C2' C3' C4' C5' 1.4(3) . . . . ?
N3' C3' C4' C5' -179.3(2) . . . . ?
C3' C4' C5' C6' -0.2(3) . . . . ?
C3' C4' C5' N5' 179.16(19) . . . . ?
O5' N5' C5' C6' -170.9(2) . . . . ?
O6' N5' C5' C6' 10.1(3) . . . . ?
O5' N5' C5' C4' 9.7(3) . . . . ?
O6' N5' C5' C4' -169.2(2) . . . . ?
C2' N1' C6' C5' -0.7(3) . . . . ?
C4' C5' C6' N1' -0.2(3) . . . . ?
N5' C5' C6' N1' -179.55(19) . . . . ?
C10P C1P C2P C3P 1.9(3) . . . . ?
C11P C1P C2P C3P -179.5(2) . . . . ?
C1P C2P C3P C4P -0.9(4) . . . . ?
C2P C3P C4P C5P -1.0(4) . . . . ?
C3P C4P C5P C6P -177.0(2) . . . . ?
C3P C4P C5P C10P 1.8(3) . . . . ?
C4P C5P C6P C7P 176.9(2) . . . . ?
C10P C5P C6P C7P -1.8(4) . . . . ?
C5P C6P C7P C8P 1.7(4) . . . . ?
C6P C7P C8P C9P -0.1(4) . . . . ?
C7P C8P C9P C10P -1.4(3) . . . . ?
C7P C8P C9P C19P 180.0(2) . . . . ?
C2P C1P C10P C5P -1.1(3) . . . . ?
C11P C1P C10P C5P -179.7(2) . . . . ?
C2P C1P C10P C9P 176.6(2) . . . . ?
C11P C1P C10P C9P -2.0(3) . . . . ?
C6P C5P C10P C1P 178.0(2) . . . . ?
C4P C5P C10P C1P -0.7(3) . . . . ?
C6P C5P C10P C9P 0.3(3) . . . . ?
C4P C5P C10P C9P -178.5(2) . . . . ?
C8P C9P C10P C1P -176.4(2) . . . . ?
C19P C9P C10P C1P 2.2(3) . . . . ?
C8P C9P C10P C5P 1.3(3) . . . . ?
C19P C9P C10P C5P 179.9(2) . . . . ?
C2P C1P C11P C12P 4.0(3) . . . . ?
C10P C1P C11P C12P -177.4(2) . . . . ?
C2P C1P C11P C20P -176.5(2) . . . . ?
C10P C1P C11P C20P 2.1(3) . . . . ?
C20P C11P C12P C13P 1.3(3) . . . . ?
C1P C11P C12P C13P -179.3(2) . . . . ?
C11P C12P C13P C14P 0.3(4) . . . . ?
C12P C13P C14P C15P -2.0(4) . . . . ?
C13P C14P C15P C16P -175.8(2) . . . . ?
C13P C14P C15P C20P 2.1(4) . . . . ?
C14P C15P C16P C17P 177.6(2) . . . . ?
C20P C15P C16P C17P -0.4(4) . . . . ?
C15P C16P C17P C18P 0.8(4) . . . . ?
C16P C17P C18P C19P -0.1(4) . . . . ?
C17P C18P C19P C20P -1.0(4) . . . . ?
C17P C18P C19P C9P 179.7(2) . . . . ?
C8P C9P C19P C18P -4.6(3) . . . . ?
C10P C9P C19P C18P 176.8(2) . . . . ?
C8P C9P C19P C20P 176.1(2) . . . . ?
C10P C9P C19P C20P -2.5(3) . . . . ?
C18P C19P C20P C11P -176.7(2) . . . . ?
C9P C19P C20P C11P 2.6(3) . . . . ?
C18P C19P C20P C15P 1.4(3) . . . . ?
C9P C19P C20P C15P -179.3(2) . . . . ?
C12P C11P C20P C19P 177.0(2) . . . . ?
C1P C11P C20P C19P -2.5(3) . . . . ?
C12P C11P C20P C15P -1.0(3) . . . . ?
C1P C11P C20P C15P 179.5(2) . . . . ?
C16P C15P C20P C19P -0.7(3) . . . . ?
C14P C15P C20P C19P -178.7(2) . . . . ?
C16P C15P C20P C11P 177.4(2) . . . . ?
C14P C15P C20P C11P -0.6(3) . . . . ?

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
N1 H1 O2 0.87(3) 2.12(3) 2.742(3) 127(3) 2_655 yes
N1 H1 O3 0.87(3) 2.27(3) 3.089(3) 156(3) 2_655 yes
C6 H6 O2 0.95 2.44 2.918(3) 111.0 2_655 yes
N1' H1' O2' 0.83(3) 2.07(3) 2.703(3) 133(3) 2 yes
N1' H1' O3' 0.83(3) 2.31(3) 3.061(3) 151(3) 2 yes

_refine_diff_density_max         0.564
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.069



