#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:16:40 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281439 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/59/7245966.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7245966
loop_
_publ_author_name
'García-Raso, Angel'
'Terrón, Angel'
'Fiol, Juan J.'
'López-Zafra, Adela'
'Picó, Gemma'
'Vázquez-López, Ezequiel M.'
'Barceló-Oliver, Miquel'
'Frontera, Antonio'
_publ_section_title
;
 Synthesis, structural characterization and DFT study of
 N-(pyrimidyl)-ω-amino acids/peptide: β-alanine, γ-aminobutyric acid,
 5-aminovaleric acid, 6-aminohexanoic acid and glycylglycine
;
_journal_issue                   2
_journal_name_full               CrystEngComm
_journal_page_first              233
_journal_page_last               244
_journal_paper_doi               10.1039/D2CE01293F
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C8 H12 N3 O2, N O3'
_chemical_formula_sum            'C8 H12 N4 O5'
_chemical_formula_weight         244.22
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-11-15
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2022-11-15 deposited with the CCDC.	2022-11-24 downloaded from the CCDC.
;
_cell_angle_alpha                101.543(3)
_cell_angle_beta                 96.517(3)
_cell_angle_gamma                94.398(2)
_cell_formula_units_Z            8
_cell_length_a                   9.8280(10)
_cell_length_b                   14.0136(14)
_cell_length_c                   15.9826(16)
_cell_measurement_reflns_used    9738
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      66.492
_cell_measurement_theta_min      5.311
_cell_volume                     2131.6(4)
_computing_cell_refinement       'Bruker Apex3, 2016'
_computing_data_collection       'Bruker Apex3, 2016'
_computing_data_reduction        'SAINT v8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      100.00
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0634
_diffrn_reflns_av_unetI/netI     0.0578
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            33594
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        66.558
_diffrn_reflns_theta_max         66.558
_diffrn_reflns_theta_min         2.847
_exptl_absorpt_coefficient_mu    1.103
_exptl_absorpt_correction_T_max  0.7528
_exptl_absorpt_correction_T_min  0.3844
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1442 before and 0.1014 after correction.
The Ratio of minimum to maximum transmission is 0.5106.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.522
_exptl_crystal_description       prism
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.362
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       0.0095(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2019/1 (Sheldrick 2019)'
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     618
_refine_ls_number_reflns         7442
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0535
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0990P)²+0.6163P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1558
_refine_ls_wR_factor_ref         0.1572
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7193
_reflns_number_total             7442
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ce01293f2.cif
_cod_data_source_block           1_a
_cod_depositor_comments
'Adding full bibliography for 7245964--7245971.cif.'
_cod_database_code               7245966
_shelx_shelxl_version_number     2019/1
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.778
_shelx_estimated_absorpt_t_min   0.614
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3B(H3BA,H3BB), C4B(H4BA,H4BB), C5B(H5BA,H5BB), C3D(H3DA,H3DB), C4D(H4DA,
 H4DB), C5D(H5DA,H5DB), C3C(H3CA,H3CB), C4C(H4CA,H4CB), C5C(H5CA,H5CB),
 C3A(H3AA,H3AB), C4A(H4AA,H4AB), C5A(H5AA,H5AB)
2.b Aromatic/amide H refined with riding coordinates:
 N6B(H6B), N1B'(H1B'), C4B'(H4B'), C5B'(H5B'), C6B'(H6B'), N6D(H6D),
 N1D'(H1D'), C4D'(H4D'), C5D'(H5D'), C6D'(H6D'), N6C(H6C), N1C'(H1C'),
 C4C'(H4C'), C5C'(H5C'), C6C'(H6C'), N6A(H6A), N1A'(H1A'), C4A'(H4A'),
 C5A'(H5A'), C6A'(H6A')
2.c Idealised tetrahedral OH refined as rotating group:
 O1B(H1B), O1D(H1D), O1C(H1C), O1A(H1A)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
O1B O 0.94144(11) 0.36594(10) 0.87559(8) 0.0344(3) Uani 1 1 d . . . . .
H1B H 0.888332 0.358900 0.912035 0.052 Uiso 1 1 calc R U . . .
C2B C 0.87675(15) 0.40315(11) 0.81430(10) 0.0270(3) Uani 1 1 d . . . . .
O2B O 0.75656(11) 0.41846(9) 0.81131(8) 0.0325(3) Uani 1 1 d . . . . .
C3B C 0.96835(16) 0.42467(13) 0.74948(11) 0.0301(4) Uani 1 1 d . . . . .
H3BA H 1.025651 0.369879 0.736134 0.036 Uiso 1 1 calc R U . . .
H3BB H 1.031149 0.484435 0.775797 0.036 Uiso 1 1 calc R U . . .
C4B C 0.89113(16) 0.43936(11) 0.66568(10) 0.0280(3) Uani 1 1 d . . . . .
H4BA H 0.957577 0.462723 0.630233 0.034 Uiso 1 1 calc R U . . .
H4BB H 0.827255 0.490027 0.678628 0.034 Uiso 1 1 calc R U . . .
C5B C 0.80965(16) 0.34395(12) 0.61491(10) 0.0275(3) Uani 1 1 d . . . . .
H5BA H 0.872575 0.291909 0.607106 0.033 Uiso 1 1 calc R U . . .
H5BB H 0.738159 0.323940 0.648686 0.033 Uiso 1 1 calc R U . . .
N6B N 0.74368(13) 0.35258(10) 0.53046(9) 0.0271(3) Uani 1 1 d . . . . .
H6B H 0.655575 0.360983 0.524198 0.033 Uiso 1 1 calc R U . . .
N1B' N 0.74073(13) 0.34998(10) 0.38539(9) 0.0276(3) Uani 1 1 d . . . . .
H1B' H 0.652539 0.358161 0.382096 0.033 Uiso 1 1 calc R U . . .
C2B' C 0.81182(16) 0.34820(11) 0.46269(10) 0.0261(3) Uani 1 1 d . . . . .
N3B' N 0.94819(13) 0.34067(10) 0.47171(9) 0.0282(3) Uani 1 1 d . . . . .
C4B' C 1.00890(16) 0.33225(12) 0.40084(11) 0.0307(4) Uani 1 1 d . . . . .
H4B' H 1.105219 0.327267 0.406181 0.037 Uiso 1 1 calc R U . . .
C5B' C 0.94021(17) 0.33023(12) 0.31892(11) 0.0319(4) Uani 1 1 d . . . . .
H5B' H 0.987287 0.322797 0.269640 0.038 Uiso 1 1 calc R U . . .
C6B' C 0.80277(17) 0.33942(12) 0.31297(11) 0.0301(4) Uani 1 1 d . . . . .
H6B' H 0.750999 0.338442 0.258807 0.036 Uiso 1 1 calc R U . . .
O1D O 0.68722(11) 0.09206(9) 0.95934(7) 0.0322(3) Uani 1 1 d . . . . .
H1D H 0.636605 0.097959 0.998661 0.048 Uiso 1 1 calc R U . . .
C2D C 0.63130(15) 0.12889(11) 0.89542(10) 0.0264(3) Uani 1 1 d . . . . .
O2D O 0.51756(11) 0.15797(9) 0.89270(7) 0.0311(3) Uani 1 1 d . . . . .
C3D C 0.72543(15) 0.13327(12) 0.82785(11) 0.0279(3) Uani 1 1 d . . . . .
H3DA H 0.755854 0.067502 0.809237 0.033 Uiso 1 1 calc R U . . .
H3DB H 0.808276 0.178672 0.854139 0.033 Uiso 1 1 calc R U . . .
C4D C 0.66079(15) 0.16640(11) 0.74887(10) 0.0267(3) Uani 1 1 d . . . . .
H4DA H 0.734257 0.186928 0.716692 0.032 Uiso 1 1 calc R U . . .
H4DB H 0.609963 0.223636 0.767323 0.032 Uiso 1 1 calc R U . . .
C5D C 0.56238(16) 0.08457(11) 0.68985(10) 0.0263(3) Uani 1 1 d . . . . .
H5DA H 0.612584 0.026343 0.674174 0.032 Uiso 1 1 calc R U . . .
H5DB H 0.487069 0.066265 0.721641 0.032 Uiso 1 1 calc R U . . .
N6D N 0.50288(13) 0.11201(10) 0.61113(9) 0.0271(3) Uani 1 1 d . . . . .
H6D H 0.417990 0.128229 0.607789 0.033 Uiso 1 1 calc R U . . .
N1D' N 0.50814(13) 0.14015(9) 0.47366(9) 0.0269(3) Uani 1 1 d . . . . .
H1D' H 0.424417 0.158272 0.474162 0.032 Uiso 1 1 calc R U . . .
C2D' C 0.57166(16) 0.11349(11) 0.54425(10) 0.0251(3) Uani 1 1 d . . . . .
N3D' N 0.70105(13) 0.08726(10) 0.54684(9) 0.0283(3) Uani 1 1 d . . . . .
C4D' C 0.76242(16) 0.08735(12) 0.47684(11) 0.0297(4) Uani 1 1 d . . . . .
H4D' H 0.853461 0.068815 0.477655 0.036 Uiso 1 1 calc R U . . .
C5D' C 0.70145(17) 0.11300(12) 0.40201(11) 0.0304(4) Uani 1 1 d . . . . .
H5D' H 0.748789 0.112038 0.353266 0.036 Uiso 1 1 calc R U . . .
C6D' C 0.57141(17) 0.13932(11) 0.40251(10) 0.0289(3) Uani 1 1 d . . . . .
H6D' H 0.525052 0.157039 0.353288 0.035 Uiso 1 1 calc R U . . .
O1C O 0.31635(11) 0.42824(9) 0.51261(8) 0.0320(3) Uani 1 1 d . . . . .
H1C H 0.364133 0.416927 0.472038 0.048 Uiso 1 1 calc R U . . .
C2C C 0.36763(15) 0.38910(12) 0.57669(10) 0.0279(4) Uani 1 1 d . . . . .
O2C O 0.47620(11) 0.35257(9) 0.57835(8) 0.0333(3) Uani 1 1 d . . . . .
C3C C 0.27378(16) 0.39160(12) 0.64546(11) 0.0295(4) Uani 1 1 d . . . . .
H3CA H 0.187891 0.348880 0.620571 0.035 Uiso 1 1 calc R U . . .
H3CB H 0.248869 0.459217 0.662695 0.035 Uiso 1 1 calc R U . . .
C4C C 0.33544(16) 0.35899(12) 0.72561(11) 0.0280(3) Uani 1 1 d . . . . .
H4CA H 0.389006 0.302989 0.708126 0.034 Uiso 1 1 calc R U . . .
H4CB H 0.260022 0.336311 0.755316 0.034 Uiso 1 1 calc R U . . .
C5C C 0.42927(16) 0.44091(12) 0.78832(11) 0.0285(3) Uani 1 1 d . . . . .
H5CA H 0.503021 0.465129 0.758154 0.034 Uiso 1 1 calc R U . . .
H5CB H 0.375041 0.496046 0.807445 0.034 Uiso 1 1 calc R U . . .
N6C N 0.49154(13) 0.40811(10) 0.86364(9) 0.0282(3) Uani 1 1 d . . . . .
H6C H 0.577753 0.394769 0.865755 0.034 Uiso 1 1 calc R U . . .
N1C' N 0.48905(14) 0.36298(10) 0.99494(9) 0.0282(3) Uani 1 1 d . . . . .
H1C' H 0.574237 0.348303 0.992846 0.034 Uiso 1 1 calc R U . . .
C2C' C 0.42367(16) 0.39749(11) 0.92924(10) 0.0267(3) Uani 1 1 d . . . . .
N3C' N 0.29417(13) 0.42193(10) 0.93044(9) 0.0298(3) Uani 1 1 d . . . . .
C4C' C 0.23311(16) 0.41082(12) 0.99874(11) 0.0306(4) Uani 1 1 d . . . . .
H4C' H 0.141965 0.428575 1.000650 0.037 Uiso 1 1 calc R U . . .
C5C' C 0.29453(17) 0.37477(12) 1.06764(11) 0.0321(4) Uani 1 1 d . . . . .
H5C' H 0.247257 0.367373 1.114970 0.039 Uiso 1 1 calc R U . . .
C6C' C 0.42573(17) 0.35073(12) 1.06351(11) 0.0305(4) Uani 1 1 d . . . . .
H6C' H 0.472419 0.325556 1.108461 0.037 Uiso 1 1 calc R U . . .
O1A O 1.05454(11) 0.16346(10) 0.59192(8) 0.0345(3) Uani 1 1 d . . . . .
H1A H 1.107371 0.164617 0.554265 0.052 Uiso 1 1 calc R U . . .
C2A C 1.11687(15) 0.12980(11) 0.65641(10) 0.0265(3) Uani 1 1 d . . . . .
O2A O 1.23671(11) 0.11317(9) 0.66100(8) 0.0315(3) Uani 1 1 d . . . . .
C3A C 1.02292(16) 0.11417(12) 0.72127(11) 0.0290(4) Uani 1 1 d . . . . .
H3AA H 0.946603 0.063900 0.692673 0.035 Uiso 1 1 calc R U . . .
H3AB H 0.982336 0.175911 0.741123 0.035 Uiso 1 1 calc R U . . .
C4A C 1.09322(16) 0.08211(12) 0.79938(10) 0.0280(3) Uani 1 1 d . . . . .
H4AA H 1.149696 0.028387 0.780055 0.034 Uiso 1 1 calc R U . . .
H4AB H 1.022561 0.056914 0.831203 0.034 Uiso 1 1 calc R U . . .
C5A C 1.18479(16) 0.16712(12) 0.85914(10) 0.0284(3) Uani 1 1 d . . . . .
H5AA H 1.258703 0.189083 0.827961 0.034 Uiso 1 1 calc R U . . .
H5AB H 1.129128 0.222497 0.874326 0.034 Uiso 1 1 calc R U . . .
N6A N 1.24739(13) 0.14235(10) 0.93835(9) 0.0296(3) Uani 1 1 d . . . . .
H6A H 1.333007 0.127610 0.941697 0.036 Uiso 1 1 calc R U . . .
N1A' N 1.24961(14) 0.12850(10) 1.08015(9) 0.0289(3) Uani 1 1 d . . . . .
H1A' H 1.337403 0.119384 1.081991 0.035 Uiso 1 1 calc R U . . .
C2A' C 1.17922(16) 0.14129(11) 1.00575(11) 0.0278(3) Uani 1 1 d . . . . .
N3A' N 1.04456(14) 0.15415(10) 0.99942(9) 0.0309(3) Uani 1 1 d . . . . .
C4A' C 0.98371(17) 0.15408(12) 1.06974(11) 0.0324(4) Uani 1 1 d . . . . .
H4A' H 0.888506 0.162878 1.066348 0.039 Uiso 1 1 calc R U . . .
C5A' C 1.05072(18) 0.14193(12) 1.14799(11) 0.0334(4) Uani 1 1 d . . . . .
H5A' H 1.003485 0.142267 1.196697 0.040 Uiso 1 1 calc R U . . .
C6A' C 1.18753(18) 0.12951(12) 1.15128(11) 0.0321(4) Uani 1 1 d . . . . .
H6A' H 1.238492 0.121657 1.203213 0.038 Uiso 1 1 calc R U . . .
N1E N 0.82109(14) 0.36044(10) 1.06522(9) 0.0292(3) Uani 1 1 d . . . . .
O2E O 0.76548(11) 0.34286(9) 0.98575(7) 0.0307(3) Uani 1 1 d . . . . .
O3E O 0.94577(12) 0.38300(10) 1.08253(8) 0.0404(3) Uani 1 1 d . . . . .
O4E O 0.74519(13) 0.35336(10) 1.12083(8) 0.0407(3) Uani 1 1 d . . . . .
N5E N 0.42343(14) -0.10476(10) 0.84449(9) 0.0309(3) Uani 1 1 d . . . . .
O6E O 0.29790(13) -0.11488(11) 0.82513(9) 0.0459(4) Uani 1 1 d . . . . .
O7E O 0.50464(13) -0.08583(9) 0.79496(8) 0.0383(3) Uani 1 1 d . . . . .
O8E O 0.47498(12) -0.11457(10) 0.91991(8) 0.0383(3) Uani 1 1 d . . . . .
N9E N 0.59534(13) -0.34501(10) 0.69163(9) 0.0296(3) Uani 1 1 d . . . . .
O10E O 0.52484(13) -0.31198(11) 0.74805(8) 0.0427(3) Uani 1 1 d . . . . .
O11E O 0.53225(12) -0.38074(10) 0.61539(8) 0.0395(3) Uani 1 1 d . . . . .
O12E O 0.72080(12) -0.34492(10) 0.70565(9) 0.0395(3) Uani 1 1 d . . . . .
N13E N 0.82458(14) -0.13344(10) 0.59825(9) 0.0298(3) Uani 1 1 d . . . . .
O14E O 0.76737(11) -0.17319(9) 0.52122(7) 0.0315(3) Uani 1 1 d . . . . .
O15E O 0.75001(13) -0.11791(10) 0.65591(8) 0.0407(3) Uani 1 1 d . . . . .
O16E O 0.95044(12) -0.11283(10) 0.61193(9) 0.0411(3) Uani 1 1 d . . . . .
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'
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
C2B O1B H1B 109.5 . . ?
O1B C2B C3B 112.76(13) . . ?
O2B C2B O1B 123.22(14) . . ?
O2B C2B C3B 124.02(15) . . ?
C2B C3B H3BA 108.7 . . ?
C2B C3B H3BB 108.7 . . ?
C2B C3B C4B 114.23(13) . . ?
H3BA C3B H3BB 107.6 . . ?
C4B C3B H3BA 108.7 . . ?
C4B C3B H3BB 108.7 . . ?
C3B C4B H4BA 109.4 . . ?
C3B C4B H4BB 109.4 . . ?
C3B C4B C5B 111.08(13) . . ?
H4BA C4B H4BB 108.0 . . ?
C5B C4B H4BA 109.4 . . ?
C5B C4B H4BB 109.4 . . ?
C4B C5B H5BA 109.0 . . ?
C4B C5B H5BB 109.0 . . ?
H5BA C5B H5BB 107.8 . . ?
N6B C5B C4B 112.89(13) . . ?
N6B C5B H5BA 109.0 . . ?
N6B C5B H5BB 109.0 . . ?
C5B N6B H6B 118.8 . . ?
C2B' N6B C5B 122.47(13) . . ?
C2B' N6B H6B 118.8 . . ?
C2B' N1B' H1B' 119.3 . . ?
C2B' N1B' C6B' 121.30(13) . . ?
C6B' N1B' H1B' 119.3 . . ?
N6B C2B' N1B' 118.60(13) . . ?
N6B C2B' N3B' 119.88(14) . . ?
N3B' C2B' N1B' 121.51(14) . . ?
C4B' N3B' C2B' 116.86(14) . . ?
N3B' C4B' H4B' 117.9 . . ?
N3B' C4B' C5B' 124.21(15) . . ?
C5B' C4B' H4B' 117.9 . . ?
C4B' C5B' H5B' 121.5 . . ?
C6B' C5B' C4B' 116.94(15) . . ?
C6B' C5B' H5B' 121.5 . . ?
N1B' C6B' C5B' 119.10(15) . . ?
N1B' C6B' H6B' 120.4 . . ?
C5B' C6B' H6B' 120.4 . . ?
C2D O1D H1D 109.5 . . ?
O1D C2D C3D 112.38(13) . . ?
O2D C2D O1D 123.48(14) . . ?
O2D C2D C3D 124.12(14) . . ?
C2D C3D H3DA 108.7 . . ?
C2D C3D H3DB 108.7 . . ?
C2D C3D C4D 114.36(13) . . ?
H3DA C3D H3DB 107.6 . . ?
C4D C3D H3DA 108.7 . . ?
C4D C3D H3DB 108.7 . . ?
C3D C4D H4DA 109.4 . . ?
C3D C4D H4DB 109.4 . . ?
C3D C4D C5D 111.30(13) . . ?
H4DA C4D H4DB 108.0 . . ?
C5D C4D H4DA 109.4 . . ?
C5D C4D H4DB 109.4 . . ?
C4D C5D H5DA 109.0 . . ?
C4D C5D H5DB 109.0 . . ?
H5DA C5D H5DB 107.8 . . ?
N6D C5D C4D 113.01(13) . . ?
N6D C5D H5DA 109.0 . . ?
N6D C5D H5DB 109.0 . . ?
C5D N6D H6D 118.6 . . ?
C2D' N6D C5D 122.75(13) . . ?
C2D' N6D H6D 118.6 . . ?
C2D' N1D' H1D' 119.4 . . ?
C6D' N1D' H1D' 119.4 . . ?
C6D' N1D' C2D' 121.18(13) . . ?
N6D C2D' N1D' 118.71(14) . . ?
N6D C2D' N3D' 119.99(14) . . ?
N3D' C2D' N1D' 121.29(14) . . ?
C4D' N3D' C2D' 116.96(14) . . ?
N3D' C4D' H4D' 117.9 . . ?
N3D' C4D' C5D' 124.20(15) . . ?
C5D' C4D' H4D' 117.9 . . ?
C4D' C5D' H5D' 121.6 . . ?
C6D' C5D' C4D' 116.75(15) . . ?
C6D' C5D' H5D' 121.6 . . ?
N1D' C6D' C5D' 119.60(15) . . ?
N1D' C6D' H6D' 120.2 . . ?
C5D' C6D' H6D' 120.2 . . ?
C2C O1C H1C 109.5 . . ?
O1C C2C C3C 112.32(13) . . ?
O2C C2C O1C 123.59(14) . . ?
O2C C2C C3C 124.05(15) . . ?
C2C C3C H3CA 108.7 . . ?
C2C C3C H3CB 108.7 . . ?
C2C C3C C4C 114.39(13) . . ?
H3CA C3C H3CB 107.6 . . ?
C4C C3C H3CA 108.7 . . ?
C4C C3C H3CB 108.7 . . ?
C3C C4C H4CA 109.1 . . ?
C3C C4C H4CB 109.1 . . ?
C3C C4C C5C 112.51(13) . . ?
H4CA C4C H4CB 107.8 . . ?
C5C C4C H4CA 109.1 . . ?
C5C C4C H4CB 109.1 . . ?
C4C C5C H5CA 109.2 . . ?
C4C C5C H5CB 109.2 . . ?
H5CA C5C H5CB 107.9 . . ?
N6C C5C C4C 112.14(13) . . ?
N6C C5C H5CA 109.2 . . ?
N6C C5C H5CB 109.2 . . ?
C5C N6C H6C 118.5 . . ?
C2C' N6C C5C 122.92(13) . . ?
C2C' N6C H6C 118.5 . . ?
C2C' N1C' H1C' 119.3 . . ?
C6C' N1C' H1C' 119.3 . . ?
C6C' N1C' C2C' 121.31(14) . . ?
N6C C2C' N1C' 118.48(14) . . ?
N6C C2C' N3C' 120.29(15) . . ?
N3C' C2C' N1C' 121.23(14) . . ?
C4C' N3C' C2C' 117.11(15) . . ?
N3C' C4C' H4C' 117.9 . . ?
N3C' C4C' C5C' 124.21(15) . . ?
C5C' C4C' H4C' 117.9 . . ?
C4C' C5C' H5C' 121.7 . . ?
C6C' C5C' C4C' 116.60(15) . . ?
C6C' C5C' H5C' 121.7 . . ?
N1C' C6C' C5C' 119.54(15) . . ?
N1C' C6C' H6C' 120.2 . . ?
C5C' C6C' H6C' 120.2 . . ?
C2A O1A H1A 109.5 . . ?
O1A C2A C3A 112.53(13) . . ?
O2A C2A O1A 122.82(14) . . ?
O2A C2A C3A 124.65(14) . . ?
C2A C3A H3AA 108.7 . . ?
C2A C3A H3AB 108.7 . . ?
C2A C3A C4A 114.09(12) . . ?
H3AA C3A H3AB 107.6 . . ?
C4A C3A H3AA 108.7 . . ?
C4A C3A H3AB 108.7 . . ?
C3A C4A H4AA 109.4 . . ?
C3A C4A H4AB 109.4 . . ?
C3A C4A C5A 111.03(13) . . ?
H4AA C4A H4AB 108.0 . . ?
C5A C4A H4AA 109.4 . . ?
C5A C4A H4AB 109.4 . . ?
C4A C5A H5AA 108.9 . . ?
C4A C5A H5AB 108.9 . . ?
H5AA C5A H5AB 107.7 . . ?
N6A C5A C4A 113.42(13) . . ?
N6A C5A H5AA 108.9 . . ?
N6A C5A H5AB 108.9 . . ?
C5A N6A H6A 118.9 . . ?
C2A' N6A C5A 122.24(13) . . ?
C2A' N6A H6A 118.9 . . ?
C2A' N1A' H1A' 119.4 . . ?
C6A' N1A' H1A' 119.4 . . ?
C6A' N1A' C2A' 121.23(14) . . ?
N6A C2A' N1A' 118.36(14) . . ?
N6A C2A' N3A' 120.04(14) . . ?
N3A' C2A' N1A' 121.59(14) . . ?
C4A' N3A' C2A' 116.79(15) . . ?
N3A' C4A' H4A' 117.9 . . ?
N3A' C4A' C5A' 124.21(15) . . ?
C5A' C4A' H4A' 117.9 . . ?
C4A' C5A' H5A' 121.6 . . ?
C6A' C5A' C4A' 116.80(15) . . ?
C6A' C5A' H5A' 121.6 . . ?
N1A' C6A' C5A' 119.38(16) . . ?
N1A' C6A' H6A' 120.3 . . ?
C5A' C6A' H6A' 120.3 . . ?
O3E N1E O2E 119.25(13) . . ?
O3E N1E O4E 122.82(14) . . ?
O4E N1E O2E 117.93(13) . . ?
O6E N5E O7E 123.26(14) . . ?
O6E N5E O8E 119.22(13) . . ?
O7E N5E O8E 117.52(13) . . ?
O10E N9E O11E 117.47(13) . . ?
O12E N9E O10E 122.88(14) . . ?
O12E N9E O11E 119.65(13) . . ?
O15E N13E O14E 118.16(13) . . ?
O16E N13E O14E 119.30(13) . . ?
O16E N13E O15E 122.54(14) . . ?
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
O1B H1B 0.8400 . ?
O1B C2B 1.323(2) . ?
C2B O2B 1.2140(19) . ?
C2B C3B 1.507(2) . ?
C3B H3BA 0.9900 . ?
C3B H3BB 0.9900 . ?
C3B C4B 1.522(2) . ?
C4B H4BA 0.9900 . ?
C4B H4BB 0.9900 . ?
C4B C5B 1.530(2) . ?
C5B H5BA 0.9900 . ?
C5B H5BB 0.9900 . ?
C5B N6B 1.461(2) . ?
N6B H6B 0.8800 . ?
N6B C2B' 1.330(2) . ?
N1B' H1B' 0.8800 . ?
N1B' C2B' 1.354(2) . ?
N1B' C6B' 1.356(2) . ?
C2B' N3B' 1.346(2) . ?
N3B' C4B' 1.328(2) . ?
C4B' H4B' 0.9500 . ?
C4B' C5B' 1.397(2) . ?
C5B' H5B' 0.9500 . ?
C5B' C6B' 1.361(2) . ?
C6B' H6B' 0.9500 . ?
O1D H1D 0.8400 . ?
O1D C2D 1.319(2) . ?
C2D O2D 1.2179(19) . ?
C2D C3D 1.507(2) . ?
C3D H3DA 0.9900 . ?
C3D H3DB 0.9900 . ?
C3D C4D 1.520(2) . ?
C4D H4DA 0.9900 . ?
C4D H4DB 0.9900 . ?
C4D C5D 1.526(2) . ?
C5D H5DA 0.9900 . ?
C5D H5DB 0.9900 . ?
C5D N6D 1.461(2) . ?
N6D H6D 0.8800 . ?
N6D C2D' 1.331(2) . ?
N1D' H1D' 0.8800 . ?
N1D' C2D' 1.359(2) . ?
N1D' C6D' 1.355(2) . ?
C2D' N3D' 1.349(2) . ?
N3D' C4D' 1.330(2) . ?
C4D' H4D' 0.9500 . ?
C4D' C5D' 1.400(2) . ?
C5D' H5D' 0.9500 . ?
C5D' C6D' 1.357(2) . ?
C6D' H6D' 0.9500 . ?
O1C H1C 0.8400 . ?
O1C C2C 1.324(2) . ?
C2C O2C 1.218(2) . ?
C2C C3C 1.510(2) . ?
C3C H3CA 0.9900 . ?
C3C H3CB 0.9900 . ?
C3C C4C 1.522(2) . ?
C4C H4CA 0.9900 . ?
C4C H4CB 0.9900 . ?
C4C C5C 1.530(2) . ?
C5C H5CA 0.9900 . ?
C5C H5CB 0.9900 . ?
C5C N6C 1.460(2) . ?
N6C H6C 0.8800 . ?
N6C C2C' 1.331(2) . ?
N1C' H1C' 0.8800 . ?
N1C' C2C' 1.359(2) . ?
N1C' C6C' 1.353(2) . ?
C2C' N3C' 1.344(2) . ?
N3C' C4C' 1.333(2) . ?
C4C' H4C' 0.9500 . ?
C4C' C5C' 1.397(3) . ?
C5C' H5C' 0.9500 . ?
C5C' C6C' 1.363(2) . ?
C6C' H6C' 0.9500 . ?
O1A H1A 0.8400 . ?
O1A C2A 1.325(2) . ?
C2A O2A 1.2149(19) . ?
C2A C3A 1.501(2) . ?
C3A H3AA 0.9900 . ?
C3A H3AB 0.9900 . ?
C3A C4A 1.521(2) . ?
C4A H4AA 0.9900 . ?
C4A H4AB 0.9900 . ?
C4A C5A 1.525(2) . ?
C5A H5AA 0.9900 . ?
C5A H5AB 0.9900 . ?
C5A N6A 1.461(2) . ?
N6A H6A 0.8800 . ?
N6A C2A' 1.334(2) . ?
N1A' H1A' 0.8800 . ?
N1A' C2A' 1.357(2) . ?
N1A' C6A' 1.348(2) . ?
C2A' N3A' 1.345(2) . ?
N3A' C4A' 1.332(2) . ?
C4A' H4A' 0.9500 . ?
C4A' C5A' 1.394(3) . ?
C5A' H5A' 0.9500 . ?
C5A' C6A' 1.365(3) . ?
C6A' H6A' 0.9500 . ?
N1E O2E 1.2919(18) . ?
N1E O3E 1.2274(18) . ?
N1E O4E 1.2372(18) . ?
N5E O6E 1.2275(19) . ?
N5E O7E 1.2365(19) . ?
N5E O8E 1.2912(19) . ?
N9E O10E 1.2375(19) . ?
N9E O11E 1.2871(19) . ?
N9E O12E 1.2278(18) . ?
N13E O14E 1.2893(18) . ?
N13E O15E 1.2374(18) . ?
N13E O16E 1.2328(18) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1B H1B O2E 0.84 1.81 2.6511(16) 176.7 . yes
N6B H6B O2C 0.88 2.06 2.8201(17) 144.7 . yes
N1B' H1B' O10E 0.88 2.50 3.1166(18) 127.7 2_656 yes
N1B' H1B' O11E 0.88 1.87 2.7487(18) 175.3 2_656 yes
C6B' H6B' O4E 0.95 2.25 3.107(2) 149.4 1_554 yes
O1D H1D O8E 0.84 1.79 2.6261(17) 177.4 2_657 yes
N6D H6D O2A 0.88 2.07 2.8202(17) 142.1 1_455 yes
N1D' H1D' O14E 0.88 1.92 2.7894(17) 169.0 2_656 yes
N1D' H1D' O15E 0.88 2.48 3.0415(19) 122.2 2_656 yes
C6D' H6D' O7E 0.95 2.36 3.084(2) 133.2 2_656 yes
O1C H1C O11E 0.84 1.83 2.6721(17) 174.8 2_656 yes
N6C H6C O2B 0.88 2.08 2.8266(17) 142.0 . yes
N1C' H1C' O2E 0.88 1.90 2.7701(17) 168.5 . yes
N1C' H1C' O4E 0.88 2.48 3.0683(19) 124.7 . yes
C6C' H6C' O10E 0.95 2.34 3.157(2) 144.3 2_657 yes
O1A H1A O14E 0.84 1.83 2.6707(16) 175.5 2_756 yes
O1A H1A O16E 0.84 2.59 3.1865(18) 128.6 2_756 yes
N6A H6A O2D 0.88 2.10 2.8363(17) 140.3 1_655 yes
N1A' H1A' O7E 0.88 2.51 3.1273(19) 128.0 2_757 yes
N1A' H1A' O8E 0.88 1.85 2.7288(18) 172.6 2_757 yes
C4A' H4A' O1D 0.95 2.46 3.192(2) 133.3 . yes
C6A' H6A' O15E 0.95 2.25 3.112(2) 150.0 2_757 yes
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
O1B C2B C3B C4B 163.36(14) . . . . ?
C2B C3B C4B C5B -67.45(18) . . . . ?
O2B C2B C3B C4B -16.9(2) . . . . ?
C3B C4B C5B N6B -174.92(12) . . . . ?
C4B C5B N6B C2B' 80.10(18) . . . . ?
C5B N6B C2B' N1B' 175.44(14) . . . . ?
C5B N6B C2B' N3B' -3.6(2) . . . . ?
N6B C2B' N3B' C4B' 177.09(14) . . . . ?
N1B' C2B' N3B' C4B' -1.9(2) . . . . ?
C2B' N1B' C6B' C5B' -2.3(2) . . . . ?
C2B' N3B' C4B' C5B' -0.4(2) . . . . ?
N3B' C4B' C5B' C6B' 1.3(2) . . . . ?
C4B' C5B' C6B' N1B' 0.1(2) . . . . ?
C6B' N1B' C2B' N6B -175.71(14) . . . . ?
C6B' N1B' C2B' N3B' 3.3(2) . . . . ?
O1D C2D C3D C4D 174.65(13) . . . . ?
C2D C3D C4D C5D -76.34(17) . . . . ?
O2D C2D C3D C4D -6.9(2) . . . . ?
C3D C4D C5D N6D -177.33(12) . . . . ?
C4D C5D N6D C2D' 78.09(18) . . . . ?
C5D N6D C2D' N1D' -179.88(13) . . . . ?
C5D N6D C2D' N3D' 1.2(2) . . . . ?
N6D C2D' N3D' C4D' 177.91(13) . . . . ?
N1D' C2D' N3D' C4D' -1.0(2) . . . . ?
C2D' N1D' C6D' C5D' -1.1(2) . . . . ?
C2D' N3D' C4D' C5D' 0.2(2) . . . . ?
N3D' C4D' C5D' C6D' 0.1(2) . . . . ?
C4D' C5D' C6D' N1D' 0.4(2) . . . . ?
C6D' N1D' C2D' N6D -177.44(13) . . . . ?
C6D' N1D' C2D' N3D' 1.4(2) . . . . ?
O1C C2C C3C C4C -172.89(13) . . . . ?
C2C C3C C4C C5C 82.17(17) . . . . ?
O2C C2C C3C C4C 9.3(2) . . . . ?
C3C C4C C5C N6C -178.11(12) . . . . ?
C4C C5C N6C C2C' -78.06(18) . . . . ?
C5C N6C C2C' N1C' 177.54(14) . . . . ?
C5C N6C C2C' N3C' -3.4(2) . . . . ?
N6C C2C' N3C' C4C' -179.00(14) . . . . ?
N1C' C2C' N3C' C4C' 0.0(2) . . . . ?
C2C' N1C' C6C' C5C' -1.0(2) . . . . ?
C2C' N3C' C4C' C5C' -0.7(2) . . . . ?
N3C' C4C' C5C' C6C' 0.6(2) . . . . ?
C4C' C5C' C6C' N1C' 0.3(2) . . . . ?
C6C' N1C' C2C' N6C 179.87(13) . . . . ?
C6C' N1C' C2C' N3C' 0.8(2) . . . . ?
O1A C2A C3A C4A -176.08(13) . . . . ?
C2A C3A C4A C5A 73.67(17) . . . . ?
O2A C2A C3A C4A 4.5(2) . . . . ?
C3A C4A C5A N6A 175.91(12) . . . . ?
C4A C5A N6A C2A' -80.82(19) . . . . ?
C5A N6A C2A' N1A' -172.58(14) . . . . ?
C5A N6A C2A' N3A' 6.5(2) . . . . ?
N6A C2A' N3A' C4A' -178.77(14) . . . . ?
N1A' C2A' N3A' C4A' 0.2(2) . . . . ?
C2A' N1A' C6A' C5A' 1.2(2) . . . . ?
C2A' N3A' C4A' C5A' 0.2(2) . . . . ?
N3A' C4A' C5A' C6A' 0.1(3) . . . . ?
C4A' C5A' C6A' N1A' -0.7(2) . . . . ?
C6A' N1A' C2A' N6A 178.10(14) . . . . ?
C6A' N1A' C2A' N3A' -0.9(2) . . . . ?
