#------------------------------------------------------------------------------
#$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $
#$Revision: 25271 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006654.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2006654
loop_
_publ_author_name
'Sood, G.'
'Schwalbe, C. H.'
'Fraser, W.'
_publ_section_title
;
 2,6-Diamino-9-(carboxymethyl)purine Ethyl Ester
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1624
_journal_page_last               1626
_journal_volume                  53
_journal_year                    1997
_chemical_formula_moiety         'C9 H12 N6 O2, 0.5H2 O'
_chemical_formula_sum            'C9 H13 N6 O2.5'
_chemical_formula_weight         245.25
_chemical_melting_point          446.5(5)
_chemical_name_systematic
;
 2,6-Diamino-9-(carboxymethyl)purine Ethyl Ester
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_audit_creation_method           SHELXL
_cell_angle_alpha                79.72(2)
_cell_angle_beta                 85.97(2)
_cell_angle_gamma                76.73(2)
_cell_formula_units_Z            4
_cell_length_a                   8.612(2)
_cell_length_b                   11.658(3)
_cell_length_c                   11.914(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.1
_cell_measurement_theta_min      22.8
_cell_volume                     1145.0(5)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction
;
DATREDXL (Brookhaven National Laboratory & University of Birmingham, 1986)
;
_computing_molecular_graphics    'ORTEPII (Johnson, 1976)'
_computing_publication_material  SHELXL-93
_computing_structure_refinement  'SHELXL-93 (Sheldrick, 1993)'
_computing_structure_solution
'MULTAN11/84 (Main, Germain & Woolfson, 1984)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Enraf-Nonius CAD4 diffractometer'
_diffrn_measurement_method       \w/2\q
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0253
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            4966
_diffrn_reflns_theta_max         68.00
_diffrn_reflns_theta_min         3.77
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.914
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_description       'hexagonal prism'
_exptl_crystal_F_000             516
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.173
_refine_diff_density_min         -0.208
_refine_ls_extinction_coef       0.0054(7)
_refine_ls_extinction_method     'SHELXL93 (Sheldrick, 1993)'
_refine_ls_goodness_of_fit_all   1.096
_refine_ls_goodness_of_fit_obs   1.114
_refine_ls_hydrogen_treatment
;
H atoms: see text
;
_refine_ls_matrix_type           full
_refine_ls_number_parameters     520
_refine_ls_number_reflns         4122
_refine_ls_number_restraints     96
_refine_ls_restrained_S_all      1.287
_refine_ls_restrained_S_obs      1.104
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_obs          0.0428
_refine_ls_shift/esd_max         -0.028
_refine_ls_shift/esd_mean        0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_scheme
'calc w = 1/[\s^2^(Fo^2^)+(0.0645P)^2^+0.2193P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_wR_factor_all         0.1428
_refine_ls_wR_factor_obs         0.1192
_reflns_number_observed          3921
_reflns_number_total             4126
_reflns_observed_criterion       >2sigma(I)
_[local]_cod_data_source_file    cf1160.cif
_[local]_cod_data_source_block   gs5295050
_[local]_cod_chemical_formula_sum_orig 'C9 H13 N6 O2.50'
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '446-447K' was changed to '446.5(5)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1145.0(4)
_cod_database_code               2006654
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1A 0.0488(6) 0.0351(6) 0.0446(6) -0.0068(4) -0.0070(5) -0.0110(4)
C2A 0.0407(6) 0.0391(7) 0.0460(7) -0.0070(5) -0.0024(5) -0.0143(5)
N2A 0.0599(8) 0.0406(7) 0.0660(8) -0.0121(6) -0.0143(6) -0.0161(6)
N3A 0.0459(6) 0.0433(6) 0.0475(6) -0.0079(5) -0.0089(5) -0.0144(5)
C4A 0.0414(7) 0.0408(7) 0.0429(7) -0.0042(5) -0.0066(5) -0.0112(5)
C5A 0.0467(7) 0.0364(7) 0.0450(7) -0.0064(5) -0.0076(5) -0.0106(5)
C6A 0.0431(7) 0.0374(6) 0.0409(7) -0.0060(5) -0.0053(5) -0.0112(5)
N6A 0.0698(8) 0.0368(6) 0.0487(7) -0.0117(5) -0.0217(6) -0.0066(5)
N7A 0.0666(8) 0.0360(6) 0.0542(7) -0.0096(5) -0.0174(6) -0.0063(5)
C8A 0.0687(10) 0.0383(8) 0.0551(9) -0.0062(6) -0.0181(7) -0.0041(6)
N9A 0.0547(7) 0.0445(6) 0.0471(7) -0.0028(5) -0.0174(5) -0.0068(5)
C10A 0.0493(8) 0.0560(9) 0.0463(8) 0.0007(7) -0.0157(6) -0.0090(6)
C11A 0.0465(8) 0.0486(8) 0.0534(8) -0.0078(6) -0.0075(6) -0.0034(6)
O12A 0.0451(7) 0.0960(10) 0.0782(9) -0.0048(6) -0.0071(6) -0.0108(7)
O13A 0.0541(6) 0.0861(8) 0.0459(6) -0.0010(5) -0.0040(5) -0.0123(5)
C14A 0.0741(13) 0.146(2) 0.0582(12) 0.000(2) 0.0119(10) -0.0271(13)
C15A 0.112(2) 0.160(3) 0.0544(12) 0.023(2) -0.0029(12) -0.0355(15)
N1B 0.075(5) 0.049(3) 0.039(3) -0.005(3) -0.004(2) -0.014(2)
C2B 0.048(4) 0.057(4) 0.058(8) 0.001(2) 0.003(3) -0.003(5)
N2B 0.073(4) 0.076(5) 0.073(4) 0.013(3) -0.004(2) -0.030(3)
N3B 0.050(2) 0.046(2) 0.046(2) -0.005(2) -0.0047(13) -0.013(2)
C4B 0.042(2) 0.041(2) 0.041(2) -0.008(2) -0.0034(13) -0.006(2)
C5B 0.048(3) 0.044(5) 0.041(3) -0.009(2) -0.009(2) -0.013(3)
C6B 0.051(6) 0.057(7) 0.050(8) -0.008(4) -0.015(4) 0.001(4)
N6B 0.092(6) 0.075(5) 0.058(5) -0.010(4) -0.018(4) -0.038(4)
N7B 0.045(2) 0.083(5) 0.064(3) -0.011(3) -0.002(2) -0.033(3)
C8B 0.042(2) 0.088(3) 0.063(3) -0.007(2) -0.001(2) -0.037(3)
N9B 0.044(2) 0.066(2) 0.048(2) -0.005(2) -0.0060(12) -0.025(2)
C10B 0.054(2) 0.065(2) 0.050(2) -0.0020(15) -0.0173(13) -0.0221(15)
C11B 0.0410(14) 0.069(2) 0.0428(15) -0.0077(13) -0.0007(11) -0.0202(14)
O12B 0.090(2) 0.081(2) 0.059(2) 0.010(2) -0.027(2) -0.021(2)
O13B 0.0593(13) 0.065(2) 0.0485(14) -0.0117(10) -0.0091(11) -0.0226(12)
C14B 0.062(4) 0.054(3) 0.092(6) -0.008(2) 0.011(4) -0.029(3)
C15B 0.077(3) 0.095(4) 0.104(4) -0.012(3) -0.009(3) -0.065(4)
N1C 0.042(3) 0.051(4) 0.043(4) 0.002(2) -0.013(2) -0.006(3)
C2C 0.046(5) 0.074(9) 0.024(3) -0.005(4) -0.008(3) -0.002(3)
N2C 0.042(2) 0.075(4) 0.061(3) 0.012(2) -0.010(2) -0.014(3)
N3C 0.039(2) 0.074(4) 0.034(2) -0.012(2) -0.0039(13) -0.013(3)
C4C 0.044(2) 0.057(3) 0.032(2) -0.012(2) -0.0058(13) -0.008(2)
C5C 0.040(2) 0.047(5) 0.042(3) -0.008(2) -0.004(2) -0.007(3)
C6C 0.052(6) 0.040(4) 0.026(3) -0.009(3) -0.004(3) -0.011(2)
N6C 0.038(3) 0.052(3) 0.043(3) 0.000(2) -0.016(2) -0.013(3)
N7C 0.041(2) 0.073(4) 0.054(3) -0.010(2) -0.002(2) -0.023(3)
C8C 0.046(2) 0.090(3) 0.053(2) -0.011(2) 0.006(2) -0.030(2)
N9C 0.044(2) 0.091(3) 0.042(2) -0.016(2) -0.0032(12) -0.025(2)
C10C 0.062(2) 0.109(3) 0.049(2) -0.021(2) -0.0098(15) -0.027(2)
C11C 0.055(2) 0.114(4) 0.050(2) -0.002(2) -0.0059(14) -0.023(2)
O12C 0.137(4) 0.093(3) 0.100(3) -0.031(2) -0.039(2) -0.019(2)
O13C 0.068(2) 0.103(3) 0.065(2) -0.0080(14) -0.0178(15) -0.013(2)
C14C 0.076(6) 0.116(6) 0.071(5) -0.007(4) 0.003(4) 0.003(3)
C15C 0.100(4) 0.122(6) 0.067(4) 0.015(4) -0.023(3) -0.007(3)
O1W 0.0688(8) 0.0728(8) 0.0655(8) -0.0218(6) -0.0289(7) 0.0071(6)
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
N1A 0.43050(13) 0.66879(9) 0.97631(10) 0.0424(3) Uani d D 1 . N
C2A 0.3494(2) 0.65016(12) 0.89040(12) 0.0413(3) Uani d D 1 . C
N2A 0.3321(2) 0.53604(11) 0.89667(13) 0.0538(3) Uani d D 1 . N
N3A 0.28404(13) 0.73074(10) 0.80206(10) 0.0447(3) Uani d D 1 . N
C4A 0.3045(2) 0.84005(12) 0.80866(11) 0.0417(3) Uani d D 1 . C
C5A 0.3805(2) 0.87248(11) 0.89206(12) 0.0424(3) Uani d D 1 . C
C6A 0.4481(2) 0.78019(11) 0.97914(11) 0.0401(3) Uani d D 1 . C
N6A 0.5291(2) 0.79819(12) 1.06304(11) 0.0509(3) Uani d D 1 . N
N7A 0.3757(2) 0.99434(10) 0.87015(11) 0.0519(3) Uani d D 1 . N
C8A 0.2986(2) 1.03214(13) 0.77570(14) 0.0546(4) Uani d D 1 . C
N9A 0.25034(15) 0.94390(10) 0.73426(10) 0.0494(3) Uani d D 1 . N
C10A 0.1765(2) 0.9535(2) 0.62629(13) 0.0518(4) Uani d . 1 . C
C11A 0.2972(2) 0.91906(13) 0.53402(13) 0.0503(3) Uani d . 1 . C
O12A 0.43731(13) 0.88203(13) 0.54620(12) 0.0751(4) Uani d . 1 . O
O13A 0.22250(13) 0.93309(12) 0.43735(9) 0.0641(3) Uani d D 1 . O
C14A 0.3186(3) 0.9007(3) 0.3382(2) 0.0963(8) Uani d D 1 . C
C15A 0.2073(4) 0.8923(3) 0.2526(2) 0.1155(11) Uani d D 1 . C
H10A 0.141(2) 0.9698(5) 0.2283(18) 0.133(11) Uiso calc R 1 . H
H11A 0.142(2) 0.8377(19) 0.2859(8) 0.26(3) Uiso calc R 1 . H
H12A 0.2671(4) 0.864(3) 0.1881(11) 0.208(18) Uiso calc R 1 . H
H1A 0.294(3) 0.5199(19) 0.836(2) 0.078(6) Uiso d . 1 . H
H2A 0.405(3) 0.4785(19) 0.9403(18) 0.070(5) Uiso d . 1 . H
H3A 0.563(2) 0.7387(17) 1.1195(16) 0.052(4) Uiso d . 1 . H
H4A 0.545(2) 0.8693(17) 1.0699(15) 0.056(5) Uiso d . 1 . H
H5A 0.277(2) 1.1138(18) 0.7348(16) 0.063(5) Uiso d . 1 . H
H6A 0.106(2) 0.9009(16) 0.6299(15) 0.059(5) Uiso d . 1 . H
H7A 0.123(2) 1.0324(18) 0.6014(16) 0.067(5) Uiso d . 1 . H
H8A 0.392(4) 0.826(3) 0.367(3) 0.121(10) Uiso d . 1 . H
H9A 0.372(4) 0.970(3) 0.313(3) 0.145(13) Uiso d . 1 . H
N1B 0.0388(14) 0.6806(17) 0.5341(13) 0.055(3) Uani d PD 0.50 1 N
C2B -0.0729(16) 0.677(2) 0.4604(15) 0.058(3) Uani d PD 0.50 1 C
N2B -0.2257(14) 0.7292(10) 0.4889(10) 0.076(2) Uani d PD 0.50 1 N
H1B -0.3040(14) 0.7214(10) 0.4521(10) 0.092 Uiso calc PR 0.50 1 H
H2B -0.2436(14) 0.7700(10) 0.5437(10) 0.092 Uiso calc PR 0.50 1 H
N3B -0.0548(8) 0.6142(4) 0.3733(6) 0.0472(12) Uani d PD 0.50 1 N
C4B 0.1005(6) 0.5631(4) 0.3568(5) 0.0419(11) Uani d PD 0.50 1 C
C5B 0.2261(11) 0.5664(8) 0.4194(7) 0.043(2) Uani d PD 0.50 1 C
C6B 0.1914(15) 0.631(2) 0.5087(14) 0.054(4) Uani d PD 0.50 1 C
N6B 0.3031(13) 0.6288(12) 0.5818(10) 0.073(3) Uani d PD 0.50 1 N
H3B 0.2768(13) 0.6585(12) 0.6433(10) 0.087 Uiso calc PR 0.50 1 H
H4B 0.4015(13) 0.5976(12) 0.5674(10) 0.087 Uiso calc PR 0.50 1 H
N7B 0.3692(10) 0.5068(6) 0.3748(7) 0.062(2) Uani d PD 0.50 1 N
C8B 0.3268(5) 0.4694(5) 0.2879(4) 0.0624(12) Uani d PD 0.50 1 C
H5B 0.3992(5) 0.4259(5) 0.2410(4) 0.075 Uiso calc PR 0.50 1 H
N9B 0.1663(4) 0.4998(3) 0.2715(3) 0.0520(8) Uani d PD 0.50 1 N
C10B 0.0845(4) 0.4722(3) 0.1805(3) 0.0560(7) Uani d P 0.50 1 C
H6B 0.1091(4) 0.5198(3) 0.1088(3) 0.067 Uiso calc PR 0.50 1 H
H7B -0.0298(4) 0.4941(3) 0.1951(3) 0.067 Uiso calc PR 0.50 1 H
C11B 0.1303(3) 0.3439(3) 0.1698(2) 0.0505(7) Uani d P 0.50 1 C
O12B 0.2170(5) 0.2671(4) 0.2331(3) 0.0790(10) Uani d P 0.50 1 O
O13B 0.0632(3) 0.3259(2) 0.0813(2) 0.0558(6) Uani d PD 0.50 1 O
C14B 0.0854(13) 0.2028(7) 0.0652(10) 0.069(2) Uani d PD 0.50 1 C
H8B 0.0341(13) 0.1587(7) 0.1281(10) 0.082 Uiso calc PR 0.50 1 H
H9B 0.1984(13) 0.1657(7) 0.0640(10) 0.082 Uiso calc PR 0.50 1 H
C15B 0.0160(6) 0.1989(6) -0.0429(5) 0.087(2) Uani d PD 0.50 1 C
H10B 0.019(5) 0.1174(7) -0.0488(17) 0.130 Uiso calc PR 0.50 1 H
H11B 0.077(3) 0.233(3) -0.1055(6) 0.130 Uiso calc PR 0.50 1 H
H12B -0.0925(17) 0.244(3) -0.0449(17) 0.130 Uiso calc PR 0.50 1 H
N1C 0.0355(10) 0.6913(15) 0.5469(11) 0.047(2) Uani d PD 0.50 2 N
C2C -0.0838(14) 0.693(2) 0.4766(14) 0.050(3) Uani d PD 0.50 2 C
N2C -0.2274(10) 0.7565(9) 0.5075(8) 0.062(2) Uani d PD 0.50 2 N
H1C -0.3056(10) 0.7735(9) 0.4619(8) 0.075 Uiso calc PR 0.50 2 H
H2C -0.2407(10) 0.7798(9) 0.5728(8) 0.075 Uiso calc PR 0.50 2 H
N3C -0.0705(6) 0.6596(5) 0.3746(5) 0.0485(11) Uani d PD 0.50 2 N
C4C 0.0804(6) 0.6123(4) 0.3474(4) 0.0441(11) Uani d PD 0.50 2 C
C5C 0.2126(10) 0.6009(8) 0.4116(7) 0.043(2) Uani d PD 0.50 2 C
C6C 0.1848(14) 0.6361(18) 0.5192(13) 0.038(3) Uani d PD 0.50 2 C
N6C 0.3015(8) 0.6360(9) 0.5887(8) 0.045(2) Uani d PD 0.50 2 N
H3C 0.2792(8) 0.6703(9) 0.6478(8) 0.054 Uiso calc PR 0.50 2 H
H4C 0.3985(8) 0.6016(9) 0.5739(8) 0.054 Uiso calc PR 0.50 2 H
N7C 0.3509(9) 0.5486(6) 0.3562(7) 0.0548(15) Uani d PD 0.50 2 N
C8C 0.2999(5) 0.5326(5) 0.2604(4) 0.0617(11) Uani d PD 0.50 2 C
H5C 0.3679(5) 0.5005(5) 0.2042(4) 0.074 Uiso calc PR 0.50 2 H
N9C 0.1376(4) 0.5673(4) 0.2501(3) 0.0569(8) Uani d PD 0.50 2 N
C10C 0.0455(5) 0.5688(4) 0.1509(3) 0.0709(10) Uani d P 0.50 2 C
H6C -0.0529(5) 0.5440(4) 0.1769(3) 0.085 Uiso calc PR 0.50 2 H
H7C 0.1061(5) 0.5116(4) 0.1053(3) 0.085 Uiso calc PR 0.50 2 H
C11C 0.0053(5) 0.6933(5) 0.0760(3) 0.0741(11) Uani d P 0.50 2 C
O12C 0.0387(6) 0.7807(4) 0.0929(4) 0.1072(14) Uani d P 0.50 2 O
O13C -0.0721(3) 0.6849(3) -0.0160(3) 0.0798(8) Uani d PD 0.50 2 O
C14C -0.1168(16) 0.7989(10) -0.0923(11) 0.093(4) Uani d PD 0.50 2 C
H8C -0.0249(16) 0.8337(10) -0.1147(11) 0.111 Uiso calc PR 0.50 2 H
H9C -0.1975(16) 0.8551(10) -0.0566(11) 0.111 Uiso calc PR 0.50 2 H
C15C -0.1848(9) 0.7639(8) -0.1980(6) 0.103(2) Uani d PD 0.50 2 C
H10C -0.0994(13) 0.717(4) -0.238(3) 0.155 Uiso calc PR 0.50 2 H
H11C -0.233(5) 0.8351(8) -0.249(2) 0.155 Uiso calc PR 0.50 2 H
H12C -0.264(4) 0.718(4) -0.1720(7) 0.155 Uiso calc PR 0.50 2 H
O1W 0.3540(2) 0.35457(12) 0.72316(12) 0.0691(4) Uani d . 1 . O
H1W 0.259(3) 0.367(2) 0.692(2) 0.093(7) Uiso d . 1 . H
H2W 0.417(3) 0.382(3) 0.679(3) 0.107(10) Uiso d . 1 . H
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_publ_flag
C6A N1A C2A 119.16(11) ?
N3A C2A N1A 127.55(12) yes
N3A C2A N2A 117.24(12) ?
N1A C2A N2A 115.20(13) ?
C2A N2A H1A 116.2(14) ?
C2A N2A H2A 115.5(12) ?
H1A N2A H2A 120.2(19) ?
C2A N3A C4A 111.06(11) ?
N3A C4A N9A 126.85(12) ?
N3A C4A C5A 127.64(13) ?
N9A C4A C5A 105.49(12) ?
C4A C5A N7A 110.81(12) ?
C4A C5A C6A 116.43(12) ?
N7A C5A C6A 132.76(12) ?
N6A C6A N1A 119.10(12) ?
N6A C6A C5A 122.77(12) ?
N1A C6A C5A 118.13(12) yes
C6A N6A H3A 120.0(11) ?
C6A N6A H4A 123.6(11) ?
H3A N6A H4A 116.2(16) ?
C8A N7A C5A 103.96(12) ?
N7A C8A N9A 113.67(13) ?
N7A C8A H5A 125.5(11) ?
N9A C8A H5A 120.9(11) ?
C8A N9A C4A 106.06(12) ?
C8A N9A C10A 127.45(13) ?
C4A N9A C10A 126.00(12) ?
N9A C10A C11A 112.09(12) ?
N9A C10A H6A 112.6(11) ?
C11A C10A H6A 104.3(11) ?
N9A C10A H7A 110.4(12) ?
C11A C10A H7A 106.9(12) ?
H6A C10A H7A 110.4(16) ?
O12A C11A O13A 125.38(15) ?
O12A C11A C10A 125.65(14) ?
O13A C11A C10A 108.95(12) ?
C11A O13A C14A 117.37(15) ?
O13A C14A C15A 106.9(2) ?
O13A C14A H8A 104.5(18) ?
C15A C14A H8A 114.9(17) ?
O13A C14A H9A 104.(2) ?
C15A C14A H9A 112.(2) ?
H8A C14A H9A 114.(3) ?
C14A C15A H10A 109.5(2) ?
C14A C15A H11A 109.5(2) ?
H10A C15A H11A 109.5 ?
C14A C15A H12A 109.47(13) ?
H10A C15A H12A 109.5 ?
H11A C15A H12A 109.5 ?
C6B N1B C2B 116.8(10) ?
N3B C2B N1B 128.2(10) yes
N3B C2B N2B 116.3(10) ?
N1B C2B N2B 114.8(10) ?
C2B N2B H1B 120.0(7) ?
C2B N2B H2B 120.0(7) ?
H1B N2B H2B 120.0 ?
C4B N3B C2B 110.4(7) ?
N3B C4B C5B 127.2(6) ?
N3B C4B N9B 127.2(5) ?
C5B C4B N9B 105.5(5) ?
C4B C5B C6B 116.8(8) ?
C4B C5B N7B 110.9(6) ?
C6B C5B N7B 132.2(8) ?
N6B C6B N1B 118.3(10) ?
N6B C6B C5B 120.9(10) ?
N1B C6B C5B 119.8(9) yes
C6B N6B H3B 120.0(7) ?
C6B N6B H4B 120.0(7) ?
H3B N6B H4B 120.0 ?
C8B N7B C5B 103.9(6) ?
N7B C8B N9B 113.8(5) ?
N7B C8B H5B 123.1(4) ?
N9B C8B H5B 123.1(2) ?
C8B N9B C4B 105.9(4) ?
C8B N9B C10B 126.2(3) ?
C4B N9B C10B 127.9(3) ?
N9B C10B C11B 112.6(3) ?
N9B C10B H6B 109.1(2) ?
C11B C10B H6B 109.1(2) ?
N9B C10B H7B 109.1(2) ?
C11B C10B H7B 109.1(2) ?
H6B C10B H7B 107.8 ?
O12B C11B O13B 124.9(3) ?
O12B C11B C10B 125.2(3) ?
O13B C11B C10B 109.9(3) ?
C11B O13B C14B 116.5(5) ?
O13B C14B C15B 109.6(7) ?
O13B C14B H8B 109.7(5) ?
C15B C14B H8B 109.7(5) ?
O13B C14B H9B 109.7(5) ?
C15B C14B H9B 109.7(4) ?
H8B C14B H9B 108.2 ?
C14B C15B H10B 109.5(4) ?
C14B C15B H11B 109.5(5) ?
H10B C15B H11B 109.5 ?
C14B C15B H12B 109.5(4) ?
H10B C15B H12B 109.5 ?
H11B C15B H12B 109.5 ?
C6C N1C C2C 117.8(10) ?
N3C C2C N2C 117.3(9) ?
N3C C2C N1C 128.0(10) yes
N2C C2C N1C 113.6(9) ?
C2C N2C H1C 120.0(6) ?
C2C N2C H2C 120.0(6) ?
H1C N2C H2C 120.0 ?
C4C N3C C2C 111.7(6) ?
N3C C4C N9C 127.6(5) ?
N3C C4C C5C 126.5(5) ?
N9C C4C C5C 105.9(5) ?
C4C C5C N7C 110.7(6) ?
C4C C5C C6C 117.1(7) ?
N7C C5C C6C 132.1(8) ?
N6C C6C N1C 117.2(9) ?
N6C C6C C5C 123.8(9) ?
N1C C6C C5C 118.1(9) yes
C6C N6C H3C 120.0(6) ?
C6C N6C H4C 120.0(6) ?
H3C N6C H4C 120.0 ?
C8C N7C C5C 103.6(6) ?
N7C C8C N9C 114.2(5) ?
N7C C8C H5C 122.9(4) ?
N9C C8C H5C 122.9(2) ?
C8C N9C C4C 105.7(3) ?
C8C N9C C10C 127.4(3) ?
C4C N9C C10C 126.6(4) ?
N9C C10C C11C 112.3(3) ?
N9C C10C H6C 109.1(2) ?
C11C C10C H6C 109.1(2) ?
N9C C10C H7C 109.1(2) ?
C11C C10C H7C 109.1(2) ?
H6C C10C H7C 107.9 ?
O12C C11C O13C 125.0(5) ?
O12C C11C C10C 126.7(4) ?
O13C C11C C10C 108.3(4) ?
C11C O13C C14C 112.5(5) ?
O13C C14C C15C 103.1(8) ?
O13C C14C H8C 111.1(5) ?
C15C C14C H8C 111.1(6) ?
O13C C14C H9C 111.1(6) ?
C15C C14C H9C 111.1(5) ?
H8C C14C H9C 109.1 ?
C14C C15C H10C 109.5(6) ?
C14C C15C H11C 109.5(5) ?
H10C C15C H11C 109.5 ?
C14C C15C H12C 109.5(6) ?
H10C C15C H12C 109.5 ?
H11C C15C H12C 109.5 ?
H1W O1W H2W 112.(3) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
N1A C6A 1.348(2) ?
N1A C2A 1.353(2) ?
C2A N3A 1.340(2) ?
C2A N2A 1.361(2) yes
N2A H1A 0.88(2) ?
N2A H2A 0.92(2) ?
N3A C4A 1.342(2) ?
C4A N9A 1.373(2) ?
C4A C5A 1.378(2) ?
C5A N7A 1.389(2) ?
C5A C6A 1.404(2) ?
C6A N6A 1.331(2) yes
N6A H3A 0.89(2) ?
N6A H4A 0.89(2) ?
N7A C8A 1.302(2) ?
C8A N9A 1.372(2) ?
C8A H5A 0.97(2) ?
N9A C10A 1.450(2) yes
C10A C11A 1.502(2) ?
C10A H6A 0.95(2) ?
C10A H7A 0.93(2) ?
C11A O12A 1.194(2) ?
C11A O13A 1.325(2) ?
O13A C14A 1.449(2) ?
C14A C15A 1.477(4) ?
C14A H8A 0.97(3) ?
C14A H9A 1.01(3) ?
C15A H10A 0.96 ?
C15A H11A 0.96 ?
C15A H12A 0.96 ?
N1B C6B 1.345(12) ?
N1B C2B 1.360(12) ?
C2B N3B 1.353(12) ?
C2B N2B 1.365(12) yes
N2B H1B 0.86 ?
N2B H2B 0.86 ?
N3B C4B 1.349(8) ?
C4B C5B 1.367(9) ?
C4B N9B 1.376(6) ?
C5B C6B 1.389(11) ?
C5B N7B 1.389(10) ?
C6B N6B 1.336(11) yes
N6B H3B 0.86 ?
N6B H4B 0.86 ?
N7B C8B 1.297(9) ?
C8B N9B 1.365(6) ?
C8B H5B 0.93 ?
N9B C10B 1.453(4) yes
C10B C11B 1.483(5) ?
C10B H6B 0.97 ?
C10B H7B 0.97 ?
C11B O12B 1.208(5) ?
C11B O13B 1.307(4) ?
O13B C14B 1.449(7) ?
C14B C15B 1.469(11) ?
C14B H8B 0.97 ?
C14B H9B 0.97 ?
C15B H10B 0.96 ?
C15B H11B 0.96 ?
C15B H12B 0.96 ?
N1C C6C 1.346(11) ?
N1C C2C 1.364(11) ?
C2C N3C 1.332(11) ?
C2C N2C 1.350(11) yes
N2C H1C 0.86 ?
N2C H2C 0.86 ?
N3C C4C 1.332(7) ?
C4C N9C 1.371(6) ?
C4C C5C 1.385(9) ?
C5C N7C 1.388(10) ?
C5C C6C 1.403(11) ?
C6C N6C 1.346(11) yes
N6C H3C 0.86 ?
N6C H4C 0.86 ?
N7C C8C 1.309(9) ?
C8C N9C 1.371(6) ?
C8C H5C 0.93 ?
N9C C10C 1.465(4) yes
C10C C11C 1.541(7) ?
C10C H6C 0.97 ?
C10C H7C 0.97 ?
C11C O12C 1.174(6) ?
C11C O13C 1.351(5) ?
O13C C14C 1.457(12) ?
C14C C15C 1.580(12) ?
C14C H8C 0.97 ?
C14C H9C 0.97 ?
C15C H10C 0.96 ?
C15C H11C 0.96 ?
C15C H12C 0.96 ?
O1W H1W 0.89(3) ?
O1W H2W 0.81(3) ?
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_publ_flag
C6A N1A C2A N3A 1.7(2) ?
C6A N1A C2A N2A -177.56(12) ?
N1A C2A N3A C4A -1.7(2) ?
N2A C2A N3A C4A 177.61(12) ?
C2A N3A C4A N9A -178.56(13) ?
C2A N3A C4A C5A -0.1(2) ?
N3A C4A C5A N7A -179.24(13) ?
N9A C4A C5A N7A -0.5(2) ?
N3A C4A C5A C6A 1.6(2) ?
N9A C4A C5A C6A -179.65(12) ?
C2A N1A C6A N6A -179.37(12) ?
C2A N1A C6A C5A 0.1(2) ?
C4A C5A C6A N6A 177.89(13) ?
N7A C5A C6A N6A -1.0(2) ?
C4A C5A C6A N1A -1.5(2) ?
N7A C5A C6A N1A 179.58(14) ?
C4A C5A N7A C8A -0.1(2) ?
C6A C5A N7A C8A 178.8(2) ?
C5A N7A C8A N9A 0.8(2) ?
N7A C8A N9A C4A -1.1(2) ?
N7A C8A N9A C10A -173.46(15) ?
N3A C4A N9A C8A 179.66(14) ?
C5A C4A N9A C8A 0.9(2) ?
N3A C4A N9A C10A -7.8(2) ?
C5A C4A N9A C10A 173.42(13) ?
C8A N9A C10A C11A 93.0(2) yes
C4A N9A C10A C11A -77.9(2) ?
N9A C10A C11A O12A 3.5(2) ?
N9A C10A C11A O13A -178.25(13) ?
O12A C11A O13A C14A 0.1(3) ?
C10A C11A O13A C14A -178.1(2) ?
C11A O13A C14A C15A 164.8(2) ?
C6B N1B C2B N3B 11.(4) ?
C6B N1B C2B N2B -179.(2) ?
N1B C2B N3B C4B -8.(3) ?
N2B C2B N3B C4B -177.5(16) ?
C2B N3B C4B C5B 2.7(16) ?
C2B N3B C4B N9B -175.1(13) ?
N3B C4B C5B C6B -1.2(16) ?
N9B C4B C5B C6B 177.0(13) ?
N3B C4B C5B N7B -178.0(6) ?
N9B C4B C5B N7B 0.2(9) ?
C2B N1B C6B N6B -177.(2) ?
C2B N1B C6B C5B -8.(4) ?
C4B C5B C6B N6B 172.8(16) ?
N7B C5B C6B N6B -11.(3) ?
C4B C5B C6B N1B 4.(3) ?
N7B C5B C6B N1B 180.0(16) ?
C4B C5B N7B C8B -0.1(9) ?
C6B C5B N7B C8B -176.3(16) ?
C5B N7B C8B N9B 0.0(8) ?
N7B C8B N9B C4B 0.1(7) ?
N7B C8B N9B C10B 178.9(5) ?
N3B C4B N9B C8B 178.1(5) ?
C5B C4B N9B C8B -0.1(6) ?
N3B C4B N9B C10B -0.8(8) ?
C5B C4B N9B C10B -179.0(6) ?
C8B N9B C10B C11B 50.8(6) yes
C4B N9B C10B C11B -130.6(4) ?
N9B C10B C11B O12B 4.9(5) ?
N9B C10B C11B O13B -175.0(3) ?
O12B C11B O13B C14B 5.3(7) ?
C10B C11B O13B C14B -174.8(6) ?
C11B O13B C14B C15B -174.7(5) ?
C6C N1C C2C N3C -9.(4) ?
C6C N1C C2C N2C -176.3(18) ?
N2C C2C N3C C4C 171.6(15) ?
N1C C2C N3C C4C 5.(3) ?
C2C N3C C4C N9C 179.3(13) ?
C2C N3C C4C C5C -2.3(15) ?
N3C C4C C5C N7C -179.3(6) ?
N9C C4C C5C N7C -0.6(9) ?
N3C C4C C5C C6C 4.1(15) ?
N9C C4C C5C C6C -177.2(12) ?
C2C N1C C6C N6C 179.(2) ?
C2C N1C C6C C5C 10.(3) ?
C4C C5C C6C N6C -176.5(14) ?
N7C C5C C6C N6C 8.(3) ?
C4C C5C C6C N1C -8.(2) ?
N7C C5C C6C N1C 176.4(14) ?
C4C C5C N7C C8C 1.4(9) ?
C6C C5C N7C C8C 177.3(15) ?
C5C N7C C8C N9C -1.8(8) ?
N7C C8C N9C C4C 1.5(7) ?
N7C C8C N9C C10C 175.4(5) ?
N3C C4C N9C C8C 178.2(5) ?
C5C C4C N9C C8C -0.5(6) ?
N3C C4C N9C C10C 4.3(8) ?
C5C C4C N9C C10C -174.5(6) ?
C8C N9C C10C C11C -97.0(6) yes
C4C N9C C10C C11C 75.6(5) ?
N9C C10C C11C O12C -1.3(6) ?
N9C C10C C11C O13C 176.9(3) ?
O12C C11C O13C C14C -2.3(9) ?
C10C C11C O13C C14C 179.5(7) ?
C11C O13C C14C C15C 173.5(6) ?