#------------------------------------------------------------------------------
#$Date: 2020-10-06 14:16:58 +0300 (Tue, 06 Oct 2020) $
#$Revision: 257988 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/03/7240369.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_7240369
loop_
_publ_author_name
'Carnero, Alejandro'
'Martín-Nieves, Virginia'
'Sanghvi, Yogesh S.'
'Russel, Olivia O.'
'Bassit, Leda'
'Schinazi, Raymond F.'
'Fernández, Susana'
'Ferrero, Miguel'
_publ_section_title
;
 Novel 1′-homo-N-2′-deoxy-α-nucleosides: synthesis,
 characterization and biological activity
;
_journal_issue                   27
_journal_name_full               'RSC Advances'
_journal_page_first              15815
_journal_page_last               15824
_journal_paper_doi               10.1039/D0RA03254A
_journal_volume                  10
_journal_year                    2020
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C11 H15 N5 O3'
_chemical_formula_sum            'C11 H15 N5 O3'
_chemical_formula_weight         265.28
_chemical_name_systematic        1'-Homo-N-2'-deoxy-alfa-adenosine
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_symmetry_cell_setting           monoclinic
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2018-07-10
_audit_creation_method           'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_audit_update_record
;
2020-01-28 deposited with the CCDC.	2020-04-15 downloaded from the CCDC.
;
_cell_angle_alpha                90.0
_cell_angle_beta                 117.058(4)
_cell_angle_gamma                90.0
_cell_formula_units_Z            6
_cell_length_a                   15.8711(6)
_cell_length_b                   8.04111(18)
_cell_length_c                   16.4342(5)
_cell_measurement_reflns_used    5358
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      68.9410
_cell_measurement_theta_min      3.0090
_cell_volume                     1867.79(12)
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SIR2004 (Burla, 2005)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.2640
_diffrn_detector_type            Onyx
_diffrn_measured_fraction_theta_full 0.9954
_diffrn_measured_fraction_theta_max 0.6925
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -68.00  18.90   1.10    8.00    --  -43.48  37.00  90.00   79
  2  ω   -112.00 -80.10   1.10    8.00    --  -43.48 -99.00  30.00   29
  3  ω   -125.00 -82.10   1.10    8.00    --  -43.48 -99.00 150.00   39
  4  ω     54.00 125.50   1.10   37.50    --   94.50 -77.00 -30.00   65
  5  ω     70.00  97.50   1.10   37.50    --   94.50-125.00   0.00   25
  6  ω     62.00  87.30   1.10   37.50    --   94.50 -45.00 -30.00   23
  7  ω     69.00 164.70   1.10   37.50    --   94.50  30.00 -60.00   87
  8  ω    120.00 158.50   1.10   37.50    --   94.50  45.00-180.00   35
  9  ω    127.00 153.40   1.10   37.50    --   94.50 125.00-150.00   24
 10  ω     95.00 120.30   1.10   37.50    --   94.50 125.00-180.00   23
 11  ω     72.00  96.20   1.10   37.50    --   94.50  45.00-180.00   22
 12  ω     49.00 111.70   1.10   37.50    --   94.50 -45.00-180.00   57
 13  ω     26.00  60.10   1.10   37.50    --   94.50 -45.00 -30.00   31
 14  ω     78.00 109.90   1.10   37.50    --   94.50 -30.00 120.00   29
 15  ω     99.00 124.30   1.10   37.50    --   94.50 -77.00 120.00   23
 16  ω     27.00  71.00   1.10   37.50    --   94.50 -77.00 120.00   40
 17  ω     24.00  58.10   1.10   37.50    --   94.50 -30.00 120.00   31
 18  ω   -107.00 -80.60   1.10    8.00    --  -43.48 -99.00-180.00   24
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Onyx, Nova'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0978495000
_diffrn_orient_matrix_UB_12      0.0388436000
_diffrn_orient_matrix_UB_13      -0.0063636000
_diffrn_orient_matrix_UB_21      0.0448463000
_diffrn_orient_matrix_UB_22      0.0135189000
_diffrn_orient_matrix_UB_23      0.1049244000
_diffrn_orient_matrix_UB_31      0.0171318000
_diffrn_orient_matrix_UB_32      0.1870617000
_diffrn_orient_matrix_UB_33      -0.0062373000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0486
_diffrn_reflns_av_unetI/netI     0.0367
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9891
_diffrn_reflns_point_group_measured_fraction_full 0.704
_diffrn_reflns_point_group_measured_fraction_max 0.693
_diffrn_reflns_theta_full        68.1328
_diffrn_reflns_theta_max         69.5376
_diffrn_reflns_theta_min         3.0195
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.892
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear intense white'
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_description       plate
_exptl_crystal_F_000             840
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: EtOH'
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.030
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.043
_refine_ls_abs_structure_details
;
 Flack x determined using 898 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).

 The absolute configuration was assigned by prior knowledge of
 chiral centers.
;
_refine_ls_abs_structure_Flack   0.2(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     520
_refine_ls_number_reflns         4865
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0485
_refine_ls_R_factor_gt           0.0424
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0756P)²+0.0248P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1102
_refine_ls_wR_factor_ref         0.1183
_reflns_Friedel_coverage         0.304
_reflns_Friedel_fraction_full    0.362
_reflns_Friedel_fraction_max     0.349
_reflns_number_gt                4279
_reflns_number_total             4865
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0ra03254a2.cif
_cod_data_source_block           18030_vm1_c
_cod_depositor_comments          'Adding full bibliography for 7240369.cif.'
_cod_original_cell_volume        1867.77(12)
_cod_database_code               7240369
_cell_oxdiff_length_a            15.8723(8)
_cell_oxdiff_length_b            8.0435(2)
_cell_oxdiff_length_c            16.4284(8)
_cell_oxdiff_angle_alpha         90.000(3)
_cell_oxdiff_angle_beta          117.061(5)
_cell_oxdiff_angle_gamma         90.025(3)
_cell_oxdiff_volume              1867.77(15)
_cell_oxdiff_measurement_reflns_used 5358
_oxdiff_exptl_absorpt_empirical_full_min 0.719
_oxdiff_exptl_absorpt_empirical_full_max 1.704
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_reflns_odcompleteness_completeness 99.54
_reflns_odcompleteness_theta     68.13
_reflns_odcompleteness_iscentric 1
_chemical_oxdiff_formula         C11H15N5O3
_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_min   0.776
_shelx_estimated_absorpt_t_max   0.974
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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
N1 N 0.0917(2) 1.3380(4) -0.27106(18) 0.0525(7) Uani 1 1 d . . . . .
N3 N 0.1888(2) 1.2899(4) -0.11025(18) 0.0537(7) Uani 1 1 d . . . . .
N5 N 0.17605(18) 1.0068(4) -0.06712(16) 0.0454(6) Uani 1 1 d . . . . .
N7 N 0.07548(18) 0.9031(4) -0.20436(17) 0.0453(6) Uani 1 1 d . . . . .
N10 N 0.00120(19) 1.1375(4) -0.37259(16) 0.0489(6) Uani 1 1 d . . . . .
H101 H -0.016668 1.212812 -0.416130 0.073 Uiso 1 1 calc R U . . .
H102 H -0.020370 1.035111 -0.385635 0.073 Uiso 1 1 calc R U . . .
C2 C 0.1528(3) 1.3821(5) -0.1860(2) 0.0572(9) Uani 1 1 d . . . . .
H2 H 0.173386 1.494567 -0.178426 0.086 Uiso 1 1 calc R U . . .
C4 C 0.1558(2) 1.1335(4) -0.12863(19) 0.0425(7) Uani 1 1 d . . . . .
C6 C 0.1259(2) 0.8719(5) -0.1162(2) 0.0473(7) Uani 1 1 d . . . . .
H6 H 0.127204 0.766516 -0.089587 0.071 Uiso 1 1 calc R U . . .
C8 C 0.0933(2) 1.0689(4) -0.21261(19) 0.0418(7) Uani 1 1 d . . . . .
C9 C 0.0607(2) 1.1784(4) -0.28722(19) 0.0416(7) Uani 1 1 d . . . . .
C11 C 0.2421(3) 1.0224(5) 0.0303(2) 0.0538(9) Uani 1 1 d . . . . .
H111 H 0.222134 1.117528 0.055769 0.081 Uiso 1 1 calc R U . . .
H112 H 0.305784 1.048015 0.036635 0.081 Uiso 1 1 calc R U . . .
C12 C 0.2485(3) 0.8712(5) 0.0853(2) 0.0531(8) Uani 1 1 d . . . . .
H12 H 0.184685 0.843631 0.079824 0.080 Uiso 1 1 calc R U . . .
C13 C 0.3191(3) 0.8944(6) 0.1859(2) 0.0572(9) Uani 1 1 d . . . . .
H131 H 0.369581 0.974024 0.193071 0.086 Uiso 1 1 calc R U . . .
H132 H 0.287188 0.933746 0.221928 0.086 Uiso 1 1 calc R U . . .
C14 C 0.3583(2) 0.7209(5) 0.2141(2) 0.0491(8) Uani 1 1 d . . . . .
H14 H 0.312659 0.655599 0.227849 0.074 Uiso 1 1 calc R U . . .
C15 C 0.3571(2) 0.6506(5) 0.1269(2) 0.0463(7) Uani 1 1 d . . . . .
H15 H 0.418514 0.676925 0.126576 0.069 Uiso 1 1 calc R U . . .
C18 C 0.3401(3) 0.4665(5) 0.1156(2) 0.0584(9) Uani 1 1 d . . . . .
H181 H 0.385089 0.409548 0.172157 0.088 Uiso 1 1 calc R U . . .
H182 H 0.275245 0.442305 0.106443 0.088 Uiso 1 1 calc R U . . .
O16 O 0.2830(2) 0.7350(4) 0.05356(16) 0.0780(9) Uani 1 1 d . . . . .
O17 O 0.44795(16) 0.7152(4) 0.29162(14) 0.0555(6) Uani 1 1 d . . . . .
H17 H 0.488677 0.757786 0.278647 0.083 Uiso 1 1 calc R U . . .
O19 O 0.35109(17) 0.4030(4) 0.04083(16) 0.0617(7) Uani 1 1 d . . . . .
H19 H 0.298335 0.371480 -0.000098 0.093 Uiso 1 1 calc R U . . .
N21 N 0.9034(2) -0.1764(4) 0.89969(19) 0.0542(7) Uani 1 1 d . . . . .
N23 N 0.8192(2) -0.1222(4) 0.73831(18) 0.0537(7) Uani 1 1 d . . . . .
N25 N 0.83712(18) 0.1648(4) 0.70269(15) 0.0452(6) Uani 1 1 d . . . . .
N27 N 0.9288(2) 0.2606(4) 0.84391(17) 0.0479(6) Uani 1 1 d . . . . .
N30 N 0.9882(2) 0.0217(4) 1.00776(18) 0.0582(8) Uani 1 1 d . . . . .
H301 H 1.002872 -0.054254 1.050647 0.087 Uiso 1 1 calc R U . . .
H302 H 1.008979 0.124185 1.022485 0.087 Uiso 1 1 calc R U . . .
C22 C 0.8496(3) -0.2164(5) 0.8123(2) 0.0558(9) Uani 1 1 d . . . . .
H22 H 0.830164 -0.329448 0.801524 0.084 Uiso 1 1 calc R U . . .
C24 C 0.8517(2) 0.0335(4) 0.7604(2) 0.0445(7) Uani 1 1 d . . . . .
C26 C 0.8847(2) 0.2953(5) 0.7565(2) 0.0488(8) Uani 1 1 d . . . . .
H26 H 0.885989 0.402451 0.732755 0.073 Uiso 1 1 calc R U . . .
C28 C 0.9081(2) 0.0948(4) 0.84764(19) 0.0420(7) Uani 1 1 d . . . . .
C29 C 0.9345(2) -0.0185(5) 0.9208(2) 0.0458(7) Uani 1 1 d . . . . .
C31 C 0.7807(2) 0.1629(5) 0.60274(19) 0.0497(8) Uani 1 1 d . . . . .
H311 H 0.772241 0.046349 0.581042 0.075 Uiso 1 1 calc R U . . .
H312 H 0.815738 0.222648 0.574946 0.075 Uiso 1 1 calc R U . . .
C32 C 0.6860(3) 0.2412(5) 0.5714(2) 0.0538(8) Uani 1 1 d . . . . .
H32 H 0.652529 0.188963 0.603806 0.081 Uiso 1 1 calc R U . . .
C33 C 0.6253(3) 0.2240(5) 0.4681(2) 0.0576(9) Uani 1 1 d . . . . .
H331 H 0.665128 0.207116 0.436719 0.086 Uiso 1 1 calc R U . . .
H332 H 0.580318 0.130130 0.453279 0.086 Uiso 1 1 calc R U . . .
C34 C 0.5740(2) 0.3882(5) 0.4420(2) 0.0504(8) Uani 1 1 d . . . . .
H34 H 0.517905 0.385856 0.454427 0.076 Uiso 1 1 calc R U . . .
C35 C 0.6476(2) 0.5077(5) 0.5069(2) 0.0527(8) Uani 1 1 d . . . . .
H35 H 0.693029 0.536288 0.482362 0.079 Uiso 1 1 calc R U . . .
C38 C 0.6089(3) 0.6645(6) 0.5256(3) 0.0685(10) Uani 1 1 d . . . . .
H381 H 0.552142 0.697452 0.469255 0.103 Uiso 1 1 calc R U . . .
H382 H 0.588304 0.641461 0.573032 0.103 Uiso 1 1 calc R U . . .
O36 O 0.6964(2) 0.4158(4) 0.59011(17) 0.0742(9) Uani 1 1 d . . . . .
O37 O 0.5445(2) 0.4218(4) 0.34862(16) 0.0740(8) Uani 1 1 d . . . . .
H37 H 0.507171 0.503074 0.332261 0.111 Uiso 1 1 calc R U . . .
O39 O 0.6720(3) 0.7988(5) 0.5546(2) 0.1015(13) Uani 1 1 d . . . . .
H39 H 0.708038 0.789988 0.610846 0.152 Uiso 1 1 calc R U . . .
N41 N 0.8869(2) 0.8356(4) 0.53822(18) 0.0536(7) Uani 1 1 d . . . . .
N43 N 0.77010(19) 0.7671(4) 0.38632(17) 0.0462(6) Uani 1 1 d . . . . .
N45 N 0.77804(19) 0.4776(4) 0.35003(16) 0.0442(6) Uani 1 1 d . . . . .
N47 N 0.8965(2) 0.3919(4) 0.48270(17) 0.0488(6) Uani 1 1 d . . . . .
N50 N 0.9892(2) 0.6437(4) 0.64057(18) 0.0625(8) Uani 1 1 d . . . . .
H501 H 1.012957 0.722858 0.681807 0.094 Uiso 1 1 calc R U . . .
H502 H 1.011172 0.541568 0.653983 0.094 Uiso 1 1 calc R U . . .
C42 C 0.8159(3) 0.8684(5) 0.4564(2) 0.0532(8) Uani 1 1 d . . . . .
H42 H 0.794973 0.980712 0.446772 0.080 Uiso 1 1 calc R U . . .
C44 C 0.8058(2) 0.6129(4) 0.40589(19) 0.0405(7) Uani 1 1 d . . . . .
C46 C 0.8345(2) 0.3489(5) 0.3997(2) 0.0495(8) Uani 1 1 d . . . . .
H46 H 0.829393 0.239263 0.376367 0.074 Uiso 1 1 calc R U . . .
C48 C 0.8791(2) 0.5590(4) 0.4878(2) 0.0431(7) Uani 1 1 d . . . . .
C49 C 0.9192(2) 0.6787(5) 0.5570(2) 0.0457(7) Uani 1 1 d . . . . .
C51 C 0.6977(2) 0.4757(5) 0.2577(2) 0.0496(8) Uani 1 1 d . . . . .
H511 H 0.699961 0.577980 0.225152 0.074 Uiso 1 1 calc R U . . .
H512 H 0.638134 0.478320 0.263172 0.074 Uiso 1 1 calc R U . . .
C52 C 0.6956(2) 0.3281(5) 0.2012(2) 0.0496(8) Uani 1 1 d . . . . .
H52 H 0.757195 0.320301 0.198564 0.074 Uiso 1 1 calc R U . . .
C53 C 0.6147(3) 0.3433(5) 0.1038(2) 0.0602(10) Uani 1 1 d . . . . .
H531 H 0.569845 0.431890 0.100317 0.090 Uiso 1 1 calc R U . . .
H532 H 0.639509 0.368597 0.059776 0.090 Uiso 1 1 calc R U . . .
C54 C 0.5673(2) 0.1751(5) 0.0845(2) 0.0511(8) Uani 1 1 d . . . . .
H54 H 0.601775 0.100139 0.061205 0.077 Uiso 1 1 calc R U . . .
C55 C 0.5865(2) 0.1160(5) 0.1792(2) 0.0482(7) Uani 1 1 d . . . . .
H55 H 0.539629 0.166696 0.196827 0.072 Uiso 1 1 calc R U . . .
C58 C 0.5848(3) -0.0699(5) 0.1864(3) 0.0615(10) Uani 1 1 d . . . . .
H581 H 0.527021 -0.112921 0.134261 0.092 Uiso 1 1 calc R U . . .
H582 H 0.640062 -0.116518 0.181494 0.092 Uiso 1 1 calc R U . . .
O56 O 0.67951(17) 0.1759(4) 0.23816(15) 0.0566(6) Uani 1 1 d . . . . .
O57 O 0.47062(18) 0.1742(4) 0.02078(17) 0.0696(8) Uani 1 1 d . . . . .
H57 H 0.443303 0.254990 0.031132 0.104 Uiso 1 1 calc R U . . .
O59 O 0.58659(18) -0.1267(4) 0.26845(18) 0.0684(7) Uani 1 1 d . . . . .
H59 H 0.642826 -0.143962 0.307369 0.103 Uiso 1 1 calc R U . . .
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
C2 N1 C9 118.8(3) . . ?
C2 N3 C4 110.7(3) . . ?
C4 N5 C6 106.0(2) . . ?
C4 N5 C11 123.7(3) . . ?
C6 N5 C11 130.3(3) . . ?
C6 N7 C8 104.0(3) . . ?
C9 N10 H101 120.0 . . ?
C9 N10 H102 120.0 . . ?
H101 N10 H102 120.0 . . ?
N3 C2 N1 128.9(4) . . ?
N3 C2 H2 115.6 . . ?
N1 C2 H2 115.6 . . ?
N3 C4 N5 126.5(3) . . ?
N3 C4 C8 127.3(3) . . ?
N5 C4 C8 106.2(3) . . ?
N7 C6 N5 113.3(3) . . ?
N7 C6 H6 123.3 . . ?
N5 C6 H6 123.3 . . ?
N7 C8 C4 110.5(3) . . ?
N7 C8 C9 132.9(3) . . ?
C4 C8 C9 116.6(3) . . ?
N10 C9 N1 117.5(3) . . ?
N10 C9 C8 124.8(3) . . ?
N1 C9 C8 117.8(3) . . ?
N5 C11 C12 114.2(3) . . ?
N5 C11 H111 108.7 . . ?
C12 C11 H111 108.7 . . ?
N5 C11 H112 108.7 . . ?
C12 C11 H112 108.7 . . ?
H111 C11 H112 107.6 . . ?
O16 C12 C11 109.7(3) . . ?
O16 C12 C13 106.0(3) . . ?
C11 C12 C13 111.7(3) . . ?
O16 C12 H12 109.8 . . ?
C11 C12 H12 109.8 . . ?
C13 C12 H12 109.8 . . ?
C14 C13 C12 102.5(3) . . ?
C14 C13 H131 111.3 . . ?
C12 C13 H131 111.3 . . ?
C14 C13 H132 111.3 . . ?
C12 C13 H132 111.3 . . ?
H131 C13 H132 109.2 . . ?
O17 C14 C13 114.3(3) . . ?
O17 C14 C15 114.2(3) . . ?
C13 C14 C15 103.0(2) . . ?
O17 C14 H14 108.4 . . ?
C13 C14 H14 108.4 . . ?
C15 C14 H14 108.4 . . ?
O16 C15 C18 109.6(3) . . ?
O16 C15 C14 105.7(3) . . ?
C18 C15 C14 113.9(3) . . ?
O16 C15 H15 109.2 . . ?
C18 C15 H15 109.2 . . ?
C14 C15 H15 109.2 . . ?
O19 C18 C15 112.2(3) . . ?
O19 C18 H181 109.2 . . ?
C15 C18 H181 109.2 . . ?
O19 C18 H182 109.2 . . ?
C15 C18 H182 109.2 . . ?
H181 C18 H182 107.9 . . ?
C15 O16 C12 111.4(3) . . ?
C14 O17 H17 109.5 . . ?
C18 O19 H19 109.5 . . ?
C22 N21 C29 118.9(3) . . ?
C22 N23 C24 110.6(3) . . ?
C26 N25 C24 106.0(2) . . ?
C26 N25 C31 127.6(3) . . ?
C24 N25 C31 126.3(3) . . ?
C26 N27 C28 103.6(3) . . ?
C29 N30 H301 120.0 . . ?
C29 N30 H302 120.0 . . ?
H301 N30 H302 120.0 . . ?
N23 C22 N21 129.6(4) . . ?
N23 C22 H22 115.2 . . ?
N21 C22 H22 115.2 . . ?
N23 C24 N25 127.6(3) . . ?
N23 C24 C28 126.8(3) . . ?
N25 C24 C28 105.6(3) . . ?
N27 C26 N25 114.2(3) . . ?
N27 C26 H26 122.9 . . ?
N25 C26 H26 122.9 . . ?
N27 C28 C24 110.5(3) . . ?
N27 C28 C29 132.6(3) . . ?
C24 C28 C29 116.9(3) . . ?
N30 C29 N21 119.0(3) . . ?
N30 C29 C28 123.8(3) . . ?
N21 C29 C28 117.2(3) . . ?
N25 C31 C32 112.9(3) . . ?
N25 C31 H311 109.0 . . ?
C32 C31 H311 109.0 . . ?
N25 C31 H312 109.0 . . ?
C32 C31 H312 109.0 . . ?
H311 C31 H312 107.8 . . ?
O36 C32 C31 109.9(3) . . ?
O36 C32 C33 106.3(3) . . ?
C31 C32 C33 111.9(3) . . ?
O36 C32 H32 109.6 . . ?
C31 C32 H32 109.6 . . ?
C33 C32 H32 109.6 . . ?
C34 C33 C32 102.8(3) . . ?
C34 C33 H331 111.2 . . ?
C32 C33 H331 111.2 . . ?
C34 C33 H332 111.2 . . ?
C32 C33 H332 111.2 . . ?
H331 C33 H332 109.1 . . ?
O37 C34 C33 110.3(3) . . ?
O37 C34 C35 114.4(3) . . ?
C33 C34 C35 102.2(3) . . ?
O37 C34 H34 109.9 . . ?
C33 C34 H34 109.9 . . ?
C35 C34 H34 109.9 . . ?
O36 C35 C38 109.5(3) . . ?
O36 C35 C34 104.7(3) . . ?
C38 C35 C34 115.0(3) . . ?
O36 C35 H35 109.2 . . ?
C38 C35 H35 109.2 . . ?
C34 C35 H35 109.2 . . ?
O39 C38 C35 115.0(4) . . ?
O39 C38 H381 108.5 . . ?
C35 C38 H381 108.5 . . ?
O39 C38 H382 108.5 . . ?
C35 C38 H382 108.5 . . ?
H381 C38 H382 107.5 . . ?
C32 O36 C35 110.0(3) . . ?
C34 O37 H37 109.5 . . ?
C38 O39 H39 109.5 . . ?
C42 N41 C49 118.5(3) . . ?
C42 N43 C44 110.8(3) . . ?
C44 N45 C46 106.2(2) . . ?
C44 N45 C51 124.5(3) . . ?
C46 N45 C51 129.1(3) . . ?
C46 N47 C48 104.0(3) . . ?
C49 N50 H501 120.0 . . ?
C49 N50 H502 120.0 . . ?
H501 N50 H502 120.0 . . ?
N43 C42 N41 129.3(3) . . ?
N43 C42 H42 115.3 . . ?
N41 C42 H42 115.3 . . ?
N43 C44 N45 127.3(3) . . ?
N43 C44 C48 126.7(3) . . ?
N45 C44 C48 106.0(3) . . ?
N47 C46 N45 113.5(3) . . ?
N47 C46 H46 123.3 . . ?
N45 C46 H46 123.3 . . ?
N47 C48 C44 110.3(3) . . ?
N47 C48 C49 133.4(3) . . ?
C44 C48 C49 116.3(3) . . ?
N41 C49 N50 118.8(3) . . ?
N41 C49 C48 118.3(3) . . ?
N50 C49 C48 122.9(3) . . ?
N45 C51 C52 114.3(3) . . ?
N45 C51 H511 108.7 . . ?
C52 C51 H511 108.7 . . ?
N45 C51 H512 108.7 . . ?
C52 C51 H512 108.7 . . ?
H511 C51 H512 107.6 . . ?
O56 C52 C51 111.8(3) . . ?
O56 C52 C53 106.4(3) . . ?
C51 C52 C53 110.8(3) . . ?
O56 C52 H52 109.3 . . ?
C51 C52 H52 109.3 . . ?
C53 C52 H52 109.3 . . ?
C54 C53 C52 104.4(3) . . ?
C54 C53 H531 110.9 . . ?
C52 C53 H531 110.9 . . ?
C54 C53 H532 110.9 . . ?
C52 C53 H532 110.9 . . ?
H531 C53 H532 108.9 . . ?
O57 C54 C53 115.5(3) . . ?
O57 C54 C55 113.7(3) . . ?
C53 C54 C55 102.5(3) . . ?
O57 C54 H54 108.3 . . ?
C53 C54 H54 108.3 . . ?
C55 C54 H54 108.3 . . ?
O56 C55 C58 109.4(3) . . ?
O56 C55 C54 104.7(3) . . ?
C58 C55 C54 113.0(3) . . ?
O56 C55 H55 109.9 . . ?
C58 C55 H55 109.9 . . ?
C54 C55 H55 109.9 . . ?
O59 C58 C55 113.9(3) . . ?
O59 C58 H581 108.8 . . ?
C55 C58 H581 108.8 . . ?
O59 C58 H582 108.8 . . ?
C55 C58 H582 108.8 . . ?
H581 C58 H582 107.7 . . ?
C55 O56 C52 109.1(2) . . ?
C54 O57 H57 109.5 . . ?
C58 O59 H59 109.5 . . ?
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
N1 C2 1.338(4) . ?
N1 C9 1.357(5) . ?
N3 C2 1.333(5) . ?
N3 C4 1.343(5) . ?
N5 C4 1.367(4) . ?
N5 C6 1.370(5) . ?
N5 C11 1.467(4) . ?
N7 C6 1.321(4) . ?
N7 C8 1.383(5) . ?
N10 C9 1.328(4) . ?
N10 H101 0.8800 . ?
N10 H102 0.8800 . ?
C2 H2 0.9500 . ?
C4 C8 1.383(4) . ?
C6 H6 0.9500 . ?
C8 C9 1.403(4) . ?
C11 C12 1.491(5) . ?
C11 H111 0.9900 . ?
C11 H112 0.9900 . ?
C12 O16 1.425(5) . ?
C12 C13 1.529(4) . ?
C12 H12 1.0000 . ?
C13 C14 1.511(6) . ?
C13 H131 0.9900 . ?
C13 H132 0.9900 . ?
C14 O17 1.415(4) . ?
C14 C15 1.534(5) . ?
C14 H14 1.0000 . ?
C15 O16 1.416(4) . ?
C15 C18 1.501(6) . ?
C15 H15 1.0000 . ?
C18 O19 1.412(5) . ?
C18 H181 0.9900 . ?
C18 H182 0.9900 . ?
O17 H17 0.8400 . ?
O19 H19 0.8400 . ?
N21 C22 1.334(4) . ?
N21 C29 1.350(5) . ?
N23 C22 1.323(5) . ?
N23 C24 1.340(5) . ?
N25 C26 1.359(5) . ?
N25 C24 1.366(5) . ?
N25 C31 1.471(4) . ?
N27 C26 1.310(4) . ?
N27 C28 1.381(5) . ?
N30 C29 1.329(4) . ?
N30 H301 0.8800 . ?
N30 H302 0.8800 . ?
C22 H22 0.9500 . ?
C24 C28 1.390(4) . ?
C26 H26 0.9500 . ?
C28 C29 1.411(5) . ?
C31 C32 1.489(5) . ?
C31 H311 0.9900 . ?
C31 H312 0.9900 . ?
C32 O36 1.430(5) . ?
C32 C33 1.530(5) . ?
C32 H32 1.0000 . ?
C33 C34 1.508(6) . ?
C33 H331 0.9900 . ?
C33 H332 0.9900 . ?
C34 O37 1.411(4) . ?
C34 C35 1.515(5) . ?
C34 H34 1.0000 . ?
C35 O36 1.432(5) . ?
C35 C38 1.495(6) . ?
C35 H35 1.0000 . ?
C38 O39 1.400(6) . ?
C38 H381 0.9900 . ?
C38 H382 0.9900 . ?
O37 H37 0.8400 . ?
O39 H39 0.8400 . ?
N41 C42 1.330(4) . ?
N41 C49 1.344(5) . ?
N43 C42 1.325(5) . ?
N43 C44 1.340(4) . ?
N45 C44 1.361(4) . ?
N45 C46 1.369(4) . ?
N45 C51 1.473(4) . ?
N47 C46 1.315(4) . ?
N47 C48 1.382(5) . ?
N50 C49 1.346(4) . ?
N50 H501 0.8800 . ?
N50 H502 0.8800 . ?
C42 H42 0.9500 . ?
C44 C48 1.388(4) . ?
C46 H46 0.9500 . ?
C48 C49 1.402(5) . ?
C51 C52 1.498(5) . ?
C51 H511 0.9900 . ?
C51 H512 0.9900 . ?
C52 O56 1.439(4) . ?
C52 C53 1.535(5) . ?
C52 H52 1.0000 . ?
C53 C54 1.509(6) . ?
C53 H531 0.9900 . ?
C53 H532 0.9900 . ?
C54 O57 1.410(4) . ?
C54 C55 1.519(5) . ?
C54 H54 1.0000 . ?
C55 O56 1.431(4) . ?
C55 C58 1.501(5) . ?
C55 H55 1.0000 . ?
C58 O59 1.412(5) . ?
C58 H581 0.9900 . ?
C58 H582 0.9900 . ?
O57 H57 0.8400 . ?
O59 H59 0.8400 . ?
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
N10 H101 N47 0.88 2.16 3.001(4) 160.5 1_464 yes
N10 H102 N41 0.88 2.15 2.985(4) 157.9 1_454 yes
O17 H17 O59 0.84 1.88 2.714(4) 170.2 1_565 yes
O19 H19 N3 0.84 1.97 2.794(4) 168.4 1_545 yes
N30 H301 N27 0.88 2.16 3.027(4) 166.4 2_747 yes
N30 H302 N21 0.88 2.13 2.965(5) 158.8 2_757 yes
O37 H37 O17 0.84 1.92 2.736(4) 165.3 . yes
O39 H39 N23 0.84 2.15 2.926(4) 152.8 1_565 yes
N50 H501 N7 0.88 2.21 3.090(4) 174.4 1_656 yes
N50 H502 N1 0.88 2.10 2.940(5) 160.3 1_646 yes
O57 H57 O19 0.84 1.95 2.768(4) 164.8 . yes
O59 H59 N43 0.84 1.97 2.798(4) 167.5 1_545 yes
