#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/47/4024782.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_4024782
loop_
_publ_author_name
'Thomas E. Storr'
'Christoph G. Baumann'
'Robert J. Thatcher'
'Sara De Ornellas'
'Adrian C. Whitwood'
'Ian J. S. Fairlamb'
_publ_section_title
;
Pd(0)/Cu(I)-Mediated Direct Arylation of 2'-Deoxyadenosines: Mechanistic
Role of Cu(I) and Reactivity Comparisons with Related Purine Nucleosides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              5810
_journal_page_last               5821
_journal_paper_doi               10.1021/jo9012282
_journal_volume                  74
_journal_year                    2009
_chemical_absolute_configuration syn
_chemical_formula_moiety
'2(C16 H17 N5 O3), 2(H2 O), 0.19(O), 0.16(O), 0.15(O)'
_chemical_formula_sum            'C32 H38 N10 O8.5'
_chemical_formula_weight         698.69
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   'P 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                96.261(2)
_cell_angle_beta                 99.177(2)
_cell_angle_gamma                108.178(2)
_cell_formula_units_Z            1
_cell_length_a                   7.3242(7)
_cell_length_b                   10.7071(11)
_cell_length_c                   11.3268(12)
_cell_measurement_reflns_used    4055
_cell_measurement_temperature    110(2)
_cell_measurement_theta_max      27.36
_cell_measurement_theta_min      2.50
_cell_volume                     821.10(14)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      110(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0171
_diffrn_reflns_av_sigmaI/netI    0.0441
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11404
_diffrn_reflns_theta_full        28.31
_diffrn_reflns_theta_max         28.31
_diffrn_reflns_theta_min         1.85
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_correction_T_min  0.935
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS v2.03 (Sheldrick)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       chunk
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.039
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.6(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     579
_refine_ls_number_reflns         8037
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.028
_refine_ls_R_factor_all          0.0467
_refine_ls_R_factor_gt           0.0417
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0408P)²+0.1589P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0931
_refine_ls_wR_factor_ref         0.0961
_reflns_number_gt                7314
_reflns_number_total             8037
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9012282_si_002_2.cif
_cod_data_source_block           ijf0823m
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      P1
_cod_original_formula_sum        'C32 H38 N10 O8.50'
_cod_database_code               4024782
loop_
_symmetry_equiv_pos_as_xyz
'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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2879(3) -0.0438(2) 0.24568(19) 0.0318(4) Uani 1 1 d . . .
H1 H 0.2754 -0.0267 0.1648 0.038 Uiso 1 1 calc R . .
C2 C 0.3869(3) 0.02921(18) 0.44340(18) 0.0256(4) Uani 1 1 d . . .
C3 C 0.3124(3) -0.09774(18) 0.46895(17) 0.0236(4) Uani 1 1 d . . .
C4 C 0.2228(3) -0.20387(18) 0.36987(17) 0.0237(4) Uani 1 1 d . . .
C5 C 0.4223(3) 0.03075(19) 0.64109(18) 0.0270(4) Uani 1 1 d . . .
C6 C 0.5668(3) 0.2553(2) 0.5767(2) 0.0334(5) Uani 1 1 d . . .
H6 H 0.6133 0.2890 0.6659 0.022(5) Uiso 1 1 calc R A 1
C7 C 0.7304(3) 0.30728(19) 0.51156(18) 0.0301(4) Uani 1 1 d . C .
H7A H 0.7006 0.2549 0.4290 0.036 Uiso 1 1 calc R B 1
H7B H 0.8554 0.3037 0.5568 0.036 Uiso 1 1 calc R B 1
C8A C 0.7419(6) 0.4508(4) 0.5059(3) 0.0262(8) Uani 0.757(2) 1 d P C 1
H8A H 0.8120 0.4878 0.4419 0.031 Uiso 0.757(2) 1 calc PR C 1
C9A C 0.5244(4) 0.4349(2) 0.4774(3) 0.0300(6) Uani 0.757(2) 1 d P C 1
H9A H 0.5041 0.5145 0.5206 0.036 Uiso 0.757(2) 1 calc PR C 1
C10A C 0.4354(5) 0.4144(3) 0.3427(3) 0.0369(7) Uani 0.757(2) 1 d P C 1
H10A H 0.2905 0.3811 0.3315 0.044 Uiso 0.757(2) 1 calc PR C 1
H10B H 0.4735 0.5018 0.3150 0.044 Uiso 0.757(2) 1 calc PR C 1
C8B C 0.698(2) 0.4507(12) 0.5424(12) 0.026(2) Uani 0.243(2) 1 d P C 2
H8B H 0.7280 0.5029 0.4756 0.031 Uiso 0.243(2) 1 calc PR C 2
C9B C 0.4921(10) 0.4332(7) 0.5567(7) 0.0192(15) Uani 0.243(2) 1 d P C 2
H9B H 0.4942 0.5089 0.6177 0.023 Uiso 0.243(2) 1 calc PR C 2
C10B C 0.3445(12) 0.4228(8) 0.4400(8) 0.0292(18) Uani 0.243(2) 1 d P C 2
H10C H 0.2105 0.3953 0.4571 0.035 Uiso 0.243(2) 1 calc PR C 2
H10D H 0.3721 0.5120 0.4161 0.035 Uiso 0.243(2) 1 calc PR C 2
C11 C 0.4666(3) 0.0782(2) 0.77295(18) 0.0289(4) Uani 1 1 d . . .
C12 C 0.4413(3) 0.1963(2) 0.8230(2) 0.0355(5) Uani 1 1 d . . .
H12 H 0.3956 0.2495 0.7718 0.043 Uiso 1 1 calc R . .
C13 C 0.4838(3) 0.2341(2) 0.9482(2) 0.0440(6) Uani 1 1 d . . .
H13 H 0.4701 0.3148 0.9827 0.053 Uiso 1 1 calc R . .
C14 C 0.5459(3) 0.1551(3) 1.0232(2) 0.0446(6) Uani 1 1 d . . .
H14 H 0.5747 0.1819 1.1088 0.054 Uiso 1 1 calc R . .
C15 C 0.5663(3) 0.0366(2) 0.9738(2) 0.0384(5) Uani 1 1 d . . .
H15 H 0.6072 -0.0179 1.0256 0.046 Uiso 1 1 calc R . .
C16 C 0.5267(3) -0.0018(2) 0.84870(18) 0.0317(4) Uani 1 1 d . . .
H16 H 0.5407 -0.0827 0.8148 0.038 Uiso 1 1 calc R . .
N1 N 0.2123(2) -0.17192(15) 0.25735(14) 0.0266(3) Uani 1 1 d . . .
N2 N 0.3783(3) 0.06295(16) 0.33192(16) 0.0313(4) Uani 1 1 d . . .
N3 N 0.4634(2) 0.11182(15) 0.55476(15) 0.0265(3) Uani 1 1 d . C .
N4 N 0.3341(2) -0.09646(15) 0.59280(14) 0.0248(3) Uani 1 1 d . . .
N5 N 0.1524(3) -0.33054(17) 0.38337(16) 0.0301(4) Uani 1 1 d . . .
H5A H 0.167(3) -0.348(2) 0.454(2) 0.027(6) Uiso 1 1 d . . .
H5B H 0.092(4) -0.392(3) 0.324(3) 0.043(7) Uiso 1 1 d . . .
O1A O 0.4265(3) 0.31743(18) 0.5255(2) 0.0299(5) Uani 0.757(2) 1 d P C 1
O2A O 0.8289(19) 0.5302(14) 0.6246(8) 0.0363(16) Uani 0.757(2) 1 d P C 1
H2A H 0.962(5) 0.575(3) 0.629(3) 0.035(8) Uiso 0.757(2) 1 d P C 1
O3A O 0.4933(3) 0.32381(18) 0.26795(16) 0.0298(4) Uani 0.757(2) 1 d P C 1
H3A H 0.449(4) 0.245(3) 0.287(3) 0.026(7) Uiso 0.757(2) 1 d P C 1
O1B O 0.4215(7) 0.3101(5) 0.6030(6) 0.0200(11) Uani 0.243(2) 1 d P C 2
O2B O 0.828(6) 0.523(4) 0.653(3) 0.036(5) Uani 0.243(2) 1 d P C 2
H2B H 0.9443 0.5333 0.6471 0.054 Uiso 0.243(2) 1 calc PR C 2
O3B O 0.3499(9) 0.3320(6) 0.3426(5) 0.0298(4) Uani 0.243(2) 1 d P C 2
H3B H 0.2671 0.3306 0.2815 0.045 Uiso 0.243(2) 1 calc PR C 2
C17 C 1.0595(3) 1.18654(19) 1.07923(17) 0.0257(4) Uani 1 1 d . . .
H17 H 1.0910 1.1882 1.1642 0.031 Uiso 1 1 calc R . .
C18 C 0.9913(2) 1.07885(17) 0.89130(16) 0.0201(3) Uani 1 1 d . . .
C19 C 0.9845(2) 1.19203(18) 0.84483(16) 0.0206(3) Uani 1 1 d . . .
C20 C 1.0125(2) 1.30677(18) 0.92697(17) 0.0229(4) Uani 1 1 d . . .
C21 C 0.9207(2) 1.04068(17) 0.69079(16) 0.0200(3) Uani 1 1 d . . .
C22 C 0.9355(3) 0.84074(17) 0.79016(16) 0.0223(4) Uani 1 1 d . . .
H22 H 0.9629 0.8056 0.7118 0.027 Uiso 1 1 calc R . .
C23 C 1.0702(3) 0.81454(19) 0.89605(17) 0.0259(4) Uani 1 1 d . . .
H23A H 1.1383 0.7545 0.8665 0.031 Uiso 1 1 calc R . .
H23B H 1.1694 0.8990 0.9416 0.031 Uiso 1 1 calc R . .
C24 C 0.9301(3) 0.74848(17) 0.97518(17) 0.0260(4) Uani 1 1 d . . .
H24 H 0.9083 0.8179 1.0324 0.031 Uiso 1 1 calc R . .
C25 C 0.7435(3) 0.67496(18) 0.88080(17) 0.0263(4) Uani 1 1 d . . .
H25 H 0.7552 0.5922 0.8375 0.032 Uiso 1 1 calc R . .
C26 C 0.5593(3) 0.6400(2) 0.93106(19) 0.0358(5) Uani 1 1 d . . .
H26A H 0.5748 0.5933 1.0008 0.043 Uiso 1 1 calc R . .
H26B H 0.5327 0.7222 0.9595 0.043 Uiso 1 1 calc R . .
C27 C 0.8700(3) 0.97439(18) 0.56324(16) 0.0219(3) Uani 1 1 d . . .
C28 C 0.7421(3) 0.84392(19) 0.52271(17) 0.0262(4) Uani 1 1 d . . .
H28 H 0.6907 0.7904 0.5792 0.031 Uiso 1 1 calc R . .
C29 C 0.6902(3) 0.7927(2) 0.3996(2) 0.0379(5) Uani 1 1 d . . .
H29 H 0.6040 0.7036 0.3721 0.045 Uiso 1 1 calc R . .
C30 C 0.7625(3) 0.8699(3) 0.31683(19) 0.0405(5) Uani 1 1 d . . .
H30 H 0.7253 0.8342 0.2326 0.049 Uiso 1 1 calc R . .
C31 C 0.8889(3) 0.9988(2) 0.35619(19) 0.0375(5) Uani 1 1 d . . .
H31 H 0.9389 1.0518 0.2989 0.045 Uiso 1 1 calc R . .
C32 C 0.9436(3) 1.0518(2) 0.47910(17) 0.0277(4) Uani 1 1 d . . .
H32 H 1.0311 1.1407 0.5058 0.033 Uiso 1 1 calc R . .
N6 N 1.0509(2) 1.30224(16) 1.04605(14) 0.0267(3) Uani 1 1 d . . .
N7 N 1.0300(2) 1.07075(15) 1.01009(14) 0.0235(3) Uani 1 1 d . . .
N8 N 0.9508(2) 0.98023(14) 0.79221(13) 0.0195(3) Uani 1 1 d . . .
N9 N 0.9411(2) 1.16745(15) 0.71965(13) 0.0208(3) Uani 1 1 d . . .
N10 N 1.0107(3) 1.42413(16) 0.89182(17) 0.0281(3) Uani 1 1 d . . .
H10E H 0.947(3) 1.419(2) 0.817(2) 0.021(5) Uiso 1 1 d . . .
H10F H 0.994(4) 1.483(3) 0.947(2) 0.044(7) Uiso 1 1 d . . .
O4 O 0.73768(19) 0.76696(12) 0.79786(12) 0.0248(3) Uani 1 1 d . . .
O5 O 0.9919(2) 0.65766(14) 1.04014(13) 0.0363(4) Uani 1 1 d . . .
H5C H 1.052(4) 0.700(2) 1.109(2) 0.034(6) Uiso 1 1 d . . .
O6 O 0.4002(3) 0.55574(16) 0.83740(16) 0.0438(4) Uani 1 1 d . . .
H6A H 0.304(4) 0.529(3) 0.867(3) 0.045(8) Uiso 1 1 d . . .
O7 O 0.2231(2) 0.64450(17) 0.64366(14) 0.0375(4) Uani 1 1 d . . .
H7C H 0.302(4) 0.619(3) 0.698(3) 0.046(7) Uiso 1 1 d . . .
H7D H 0.278(4) 0.733(3) 0.650(2) 0.050(8) Uiso 1 1 d . . .
O8 O 0.9097(4) 0.42662(19) 0.23621(18) 0.0563(5) Uani 1 1 d . . .
H8C H 0.846(4) 0.467(3) 0.201(3) 0.039(9) Uiso 1 1 d . . .
H8D H 0.933(7) 0.385(5) 0.167(4) 0.116(16) Uiso 1 1 d . . .
O9 O 0.6009(18) 0.4539(13) 0.2113(12) 0.048(4) Uani 0.156(10) 1 d P D 3
O10 O 0.493(4) 0.4884(17) 0.1711(15) 0.085(11) Uani 0.154(11) 1 d P E 4
O11 O 0.3341(13) 0.5840(10) 0.1379(9) 0.047(3) Uani 0.188(6) 1 d P F 5
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'
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
N2 C1 N1 128.96(19) . . ?
N2 C1 H1 115.5 . . ?
N1 C1 H1 115.5 . . ?
N2 C2 C3 126.00(17) . . ?
N2 C2 N3 128.38(17) . . ?
C3 C2 N3 105.58(17) . . ?
C2 C3 N4 111.27(16) . . ?
C2 C3 C4 117.73(17) . . ?
N4 C3 C4 130.95(17) . . ?
N5 C4 N1 119.86(17) . . ?
N5 C4 C3 123.03(17) . . ?
N1 C4 C3 117.10(16) . . ?
N4 C5 N3 112.73(17) . . ?
N4 C5 C11 122.41(19) . . ?
N3 C5 C11 124.84(17) . . ?
O1B C6 N3 103.5(3) . . ?
O1B C6 O1A 36.1(2) . . ?
N3 C6 O1A 106.98(16) . . ?
O1B C6 C7 129.5(3) . . ?
N3 C6 C7 117.91(17) . . ?
O1A C6 C7 101.11(18) . . ?
O1B C6 H6 78.4 . . ?
N3 C6 H6 110.1 . . ?
O1A C6 H6 110.1 . . ?
C7 C6 H6 110.1 . . ?
C6 C7 C8A 104.3(2) . . ?
C6 C7 C8B 85.0(4) . . ?
C8A C7 C8B 20.1(3) . . ?
C6 C7 H7A 110.9 . . ?
C8A C7 H7A 110.9 . . ?
C8B C7 H7A 124.5 . . ?
C6 C7 H7B 110.9 . . ?
C8A C7 H7B 110.9 . . ?
C8B C7 H7B 113.9 . . ?
H7A C7 H7B 108.9 . . ?
C16 C11 C12 120.06(19) . . ?
C16 C11 C5 117.52(18) . . ?
C12 C11 C5 122.3(2) . . ?
C13 C12 C11 119.2(2) . . ?
C13 C12 H12 120.4 . . ?
C11 C12 H12 120.4 . . ?
C14 C13 C12 120.5(2) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C15 120.3(2) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C16 C15 C14 119.9(2) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C11 120.0(2) . . ?
C15 C16 H16 120.0 . . ?
C11 C16 H16 120.0 . . ?
O2A C8A C7 109.1(6) . . ?
O2A C8A C9A 108.8(6) . . ?
C7 C8A C9A 100.8(3) . . ?
O2A C8A H8A 112.5 . . ?
C7 C8A H8A 112.5 . . ?
C9A C8A H8A 112.5 . . ?
O1A C9A C10A 108.6(2) . . ?
O1A C9A C8A 105.3(2) . . ?
C10A C9A C8A 114.6(3) . . ?
O1A C9A H9A 109.4 . . ?
C10A C9A H9A 109.4 . . ?
C8A C9A H9A 109.4 . . ?
O3A C10A C9A 114.3(2) . . ?
O3A C10A H10A 108.7 . . ?
C9A C10A H10A 108.7 . . ?
O3A C10A H10B 108.7 . . ?
C9A C10A H10B 108.7 . . ?
H10A C10A H10B 107.6 . . ?
O2B C8B C9B 108.2(16) . . ?
O2B C8B C7 108.9(18) . . ?
C9B C8B C7 111.7(8) . . ?
O2B C8B H8B 109.4 . . ?
C9B C8B H8B 109.4 . . ?
C7 C8B H8B 109.4 . . ?
O1B C9B C8B 107.0(6) . . ?
O1B C9B C10B 107.0(6) . . ?
C8B C9B C10B 115.9(8) . . ?
O1B C9B H9B 108.9 . . ?
C8B C9B H9B 108.9 . . ?
C10B C9B H9B 108.9 . . ?
O3B C10B C9B 113.6(6) . . ?
O3B C10B H10C 108.9 . . ?
C9B C10B H10C 108.9 . . ?
O3B C10B H10D 108.9 . . ?
C9B C10B H10D 108.9 . . ?
H10C C10B H10D 107.7 . . ?
C1 N1 C4 118.90(16) . . ?
C1 N2 C2 111.28(16) . . ?
C2 N3 C5 106.08(15) . . ?
C2 N3 C6 126.89(18) . . ?
C5 N3 C6 127.02(17) . . ?
C5 N4 C3 104.26(16) . . ?
C4 N5 H5A 117.7(15) . . ?
C4 N5 H5B 122.4(18) . . ?
H5A N5 H5B 120(2) . . ?
C9A O1A C6 111.09(19) . . ?
C8A O2A H2A 109(2) . . ?
C10A O3A H3A 108.7(19) . . ?
C6 O1B C9B 98.1(5) . . ?
C8B O2B H2A 105(3) . . ?
C8B O2B H2B 109.5 . . ?
H2A O2B H2B 27.3 . . ?
C10B O3B H3B 109.5 . . ?
N7 C17 N6 129.26(17) . . ?
N7 C17 H17 115.4 . . ?
N6 C17 H17 115.4 . . ?
N7 C18 N8 128.53(15) . . ?
N7 C18 C19 125.52(16) . . ?
N8 C18 C19 105.95(15) . . ?
N9 C19 C18 111.29(15) . . ?
N9 C19 C20 130.81(16) . . ?
C18 C19 C20 117.84(16) . . ?
N6 C20 N10 118.70(17) . . ?
N6 C20 C19 118.23(16) . . ?
N10 C20 C19 123.01(17) . . ?
N9 C21 N8 112.98(15) . . ?
N9 C21 C27 121.33(15) . . ?
N8 C21 C27 125.68(15) . . ?
O4 C22 N8 107.92(14) . . ?
O4 C22 C23 106.22(14) . . ?
N8 C22 C23 115.07(14) . . ?
O4 C22 H22 109.2 . . ?
N8 C22 H22 109.2 . . ?
C23 C22 H22 109.2 . . ?
C24 C23 C22 103.91(15) . . ?
C24 C23 H23A 111.0 . . ?
C22 C23 H23A 111.0 . . ?
C24 C23 H23B 111.0 . . ?
C22 C23 H23B 111.0 . . ?
H23A C23 H23B 109.0 . . ?
O5 C24 C25 110.50(14) . . ?
O5 C24 C23 113.91(17) . . ?
C25 C24 C23 101.49(14) . . ?
O5 C24 H24 110.2 . . ?
C25 C24 H24 110.2 . . ?
C23 C24 H24 110.2 . . ?
O4 C25 C26 109.85(16) . . ?
O4 C25 C24 103.72(14) . . ?
C26 C25 C24 114.26(16) . . ?
O4 C25 H25 109.6 . . ?
C26 C25 H25 109.6 . . ?
C24 C25 H25 109.6 . . ?
O6 C26 C25 108.48(17) . . ?
O6 C26 H26A 110.0 . . ?
C25 C26 H26A 110.0 . . ?
O6 C26 H26B 110.0 . . ?
C25 C26 H26B 110.0 . . ?
H26A C26 H26B 108.4 . . ?
C32 C27 C28 119.40(17) . . ?
C32 C27 C21 116.89(16) . . ?
C28 C27 C21 123.51(16) . . ?
C29 C28 C27 119.75(18) . . ?
C29 C28 H28 120.1 . . ?
C27 C28 H28 120.1 . . ?
C30 C29 C28 120.6(2) . . ?
C30 C29 H29 119.7 . . ?
C28 C29 H29 119.7 . . ?
C29 C30 C31 120.0(2) . . ?
C29 C30 H30 120.0 . . ?
C31 C30 H30 120.0 . . ?
C30 C31 C32 120.36(19) . . ?
C30 C31 H31 119.8 . . ?
C32 C31 H31 119.8 . . ?
C31 C32 C27 119.92(19) . . ?
C31 C32 H32 120.0 . . ?
C27 C32 H32 120.0 . . ?
C20 N6 C17 117.90(16) . . ?
C17 N7 C18 111.18(15) . . ?
C18 N8 C21 105.37(14) . . ?
C18 N8 C22 128.54(14) . . ?
C21 N8 C22 126.07(14) . . ?
C21 N9 C19 104.41(14) . . ?
C20 N10 H10E 116.3(14) . . ?
C20 N10 H10F 116.0(17) . . ?
H10E N10 H10F 115(2) . . ?
C25 O4 C22 108.90(13) . . ?
C24 O5 H5C 106.9(17) . . ?
C26 O6 H6A 108(2) . . ?
H7C O7 H7D 107(2) . . ?
H8C O8 H8D 96(3) . . ?
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
C1 N2 1.333(3) . ?
C1 N1 1.340(3) . ?
C1 H1 0.9500 . ?
C2 N2 1.348(3) . ?
C2 C3 1.379(3) . ?
C2 N3 1.382(2) . ?
C3 N4 1.384(2) . ?
C3 C4 1.415(2) . ?
C4 N5 1.328(2) . ?
C4 N1 1.352(2) . ?
C5 N4 1.322(2) . ?
C5 N3 1.384(3) . ?
C5 C11 1.474(3) . ?
C6 O1B 1.420(5) . ?
C6 N3 1.458(2) . ?
C6 O1A 1.468(3) . ?
C6 C7 1.499(3) . ?
C6 H6 1.0000 . ?
C7 C8A 1.521(4) . ?
C7 C8B 1.635(11) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C11 C16 1.393(3) . ?
C11 C12 1.406(3) . ?
C12 C13 1.388(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.385(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.390(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.389(3) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C8A O2A 1.441(12) . ?
C8A C9A 1.525(5) . ?
C8A H8A 1.0000 . ?
C9A O1A 1.451(3) . ?
C9A C10A 1.524(4) . ?
C9A H9A 1.0000 . ?
C10A O3A 1.425(4) . ?
C10A H10A 0.9900 . ?
C10A H10B 0.9900 . ?
C8B O2B 1.43(4) . ?
C8B C9B 1.498(14) . ?
C8B H8B 1.0000 . ?
C9B O1B 1.446(9) . ?
C9B C10B 1.538(11) . ?
C9B H9B 1.0000 . ?
C10B O3B 1.403(11) . ?
C10B H10C 0.9900 . ?
C10B H10D 0.9900 . ?
N5 H5A 0.84(2) . ?
N5 H5B 0.84(3) . ?
O2A H2A 0.93(4) . ?
O3A H3A 0.87(3) . ?
O2B H2A 1.06(6) . ?
O2B H2B 0.8400 . ?
O3B H3B 0.8400 . ?
C17 N7 1.328(3) . ?
C17 N6 1.350(2) . ?
C17 H17 0.9500 . ?
C18 N7 1.348(2) . ?
C18 N8 1.379(2) . ?
C18 C19 1.384(2) . ?
C19 N9 1.380(2) . ?
C19 C20 1.396(3) . ?
C20 N6 1.343(2) . ?
C20 N10 1.362(2) . ?
C21 N9 1.316(2) . ?
C21 N8 1.399(2) . ?
C21 C27 1.473(2) . ?
C22 O4 1.439(2) . ?
C22 N8 1.460(2) . ?
C22 C23 1.536(2) . ?
C22 H22 1.0000 . ?
C23 C24 1.528(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 O5 1.420(2) . ?
C24 C25 1.520(3) . ?
C24 H24 1.0000 . ?
C25 O4 1.439(2) . ?
C25 C26 1.504(3) . ?
C25 H25 1.0000 . ?
C26 O6 1.428(3) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 C32 1.394(3) . ?
C27 C28 1.395(3) . ?
C28 C29 1.387(3) . ?
C28 H28 0.9500 . ?
C29 C30 1.377(3) . ?
C29 H29 0.9500 . ?
C30 C31 1.378(3) . ?
C30 H30 0.9500 . ?
C31 C32 1.389(3) . ?
C31 H31 0.9500 . ?
C32 H32 0.9500 . ?
N10 H10E 0.89(2) . ?
N10 H10F 0.89(3) . ?
O5 H5C 0.84(3) . ?
O6 H6A 0.82(3) . ?
O7 H7C 0.90(3) . ?
O7 H7D 0.90(3) . ?
O8 H8C 0.82(3) . ?
O8 H8D 0.93(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
O8 H8D N6 0.93(5) 2.00(5) 2.903(3) 165(4) 1_544
O8 H8C O9 0.82(3) 1.78(3) 2.346(14) 125(3) .
O7 H7D N4 0.90(3) 1.95(3) 2.789(2) 155(3) 1_565
O7 H7C O6 0.90(3) 1.91(3) 2.778(2) 162(3) .
O6 H6A N10 0.82(3) 2.17(3) 2.957(2) 163(3) 1_445
O5 H5C N1 0.84(3) 1.99(3) 2.811(2) 169(2) 1_666
N10 H10F O5 0.89(3) 2.05(3) 2.910(2) 162(2) 1_565
N10 H10E O2B 0.89(2) 2.44(4) 3.25(3) 151(2) 1_565
O2B H2B O7 0.84 2.03 2.80(4) 153.8 1_655
O3A H3A N2 0.87(3) 2.00(3) 2.864(2) 173(3) .
O2A H2A O7 0.93(4) 1.80(4) 2.723(13) 173(3) 1_655
N5 H5B O8 0.84(3) 2.02(3) 2.815(2) 158(2) 1_445
N5 H5A O7 0.84(2) 2.13(2) 2.967(2) 170(2) 1_545
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
N2 C2 C3 N4 -175.89(18) . . . . ?
N3 C2 C3 N4 2.0(2) . . . . ?
N2 C2 C3 C4 1.8(3) . . . . ?
N3 C2 C3 C4 179.68(16) . . . . ?
C2 C3 C4 N5 177.51(19) . . . . ?
N4 C3 C4 N5 -5.4(3) . . . . ?
C2 C3 C4 N1 -1.8(3) . . . . ?
N4 C3 C4 N1 175.30(19) . . . . ?
O1B C6 C7 C8A 13.9(4) . . . . ?
N3 C6 C7 C8A 155.0(2) . . . . ?
O1A C6 C7 C8A 38.9(2) . . . . ?
O1B C6 C7 C8B 19.6(6) . . . . ?
N3 C6 C7 C8B 160.7(5) . . . . ?
O1A C6 C7 C8B 44.6(5) . . . . ?
N4 C5 C11 C16 37.9(3) . . . . ?
N3 C5 C11 C16 -143.30(19) . . . . ?
N4 C5 C11 C12 -139.0(2) . . . . ?
N3 C5 C11 C12 39.7(3) . . . . ?
C16 C11 C12 C13 2.3(3) . . . . ?
C5 C11 C12 C13 179.23(18) . . . . ?
C11 C12 C13 C14 -1.5(3) . . . . ?
C12 C13 C14 C15 -0.1(3) . . . . ?
C13 C14 C15 C16 0.9(3) . . . . ?
C14 C15 C16 C11 0.0(3) . . . . ?
C12 C11 C16 C15 -1.6(3) . . . . ?
C5 C11 C16 C15 -178.60(17) . . . . ?
C6 C7 C8A O2A 73.7(6) . . . . ?
C8B C7 C8A O2A 57.0(18) . . . . ?
C6 C7 C8A C9A -40.6(3) . . . . ?
C8B C7 C8A C9A -57.4(17) . . . . ?
O2A C8A C9A O1A -88.3(6) . . . . ?
C7 C8A C9A O1A 26.2(3) . . . . ?
O2A C8A C9A C10A 152.3(6) . . . . ?
C7 C8A C9A C10A -93.1(3) . . . . ?
O1A C9A C10A O3A -74.3(3) . . . . ?
C8A C9A C10A O3A 43.2(4) . . . . ?
C6 C7 C8B O2B 93.0(15) . . . . ?
C8A C7 C8B O2B -103(2) . . . . ?
C6 C7 C8B C9B -26.4(8) . . . . ?
C8A C7 C8B C9B 137(2) . . . . ?
O2B C8B C9B O1B -89.5(18) . . . . ?
C7 C8B C9B O1B 30.3(10) . . . . ?
O2B C8B C9B C10B 151.2(17) . . . . ?
C7 C8B C9B C10B -89.0(9) . . . . ?
O1B C9B C10B O3B -70.9(8) . . . . ?
C8B C9B C10B O3B 48.4(10) . . . . ?
N2 C1 N1 C4 0.6(3) . . . . ?
N5 C4 N1 C1 -178.60(19) . . . . ?
C3 C4 N1 C1 0.8(3) . . . . ?
N1 C1 N2 C2 -0.8(3) . . . . ?
C3 C2 N2 C1 -0.5(3) . . . . ?
N3 C2 N2 C1 -177.9(2) . . . . ?
N2 C2 N3 C5 175.07(19) . . . . ?
C3 C2 N3 C5 -2.8(2) . . . . ?
N2 C2 N3 C6 -5.0(3) . . . . ?
C3 C2 N3 C6 177.14(17) . . . . ?
N4 C5 N3 C2 2.8(2) . . . . ?
C11 C5 N3 C2 -176.08(18) . . . . ?
N4 C5 N3 C6 -177.14(17) . . . . ?
C11 C5 N3 C6 4.0(3) . . . . ?
O1B C6 N3 C2 101.1(3) . . . . ?
O1A C6 N3 C2 63.8(3) . . . . ?
C7 C6 N3 C2 -49.1(3) . . . . ?
O1B C6 N3 C5 -79.1(3) . . . . ?
O1A C6 N3 C5 -116.3(2) . . . . ?
C7 C6 N3 C5 130.8(2) . . . . ?
N3 C5 N4 C3 -1.5(2) . . . . ?
C11 C5 N4 C3 177.39(17) . . . . ?
C2 C3 N4 C5 -0.4(2) . . . . ?
C4 C3 N4 C5 -177.63(19) . . . . ?
C10A C9A O1A C6 120.5(2) . . . . ?
C8A C9A O1A C6 -2.7(3) . . . . ?
O1B C6 O1A C9A 124.0(4) . . . . ?
N3 C6 O1A C9A -146.3(2) . . . . ?
C7 C6 O1A C9A -22.4(2) . . . . ?
N3 C6 O1B C9B -149.7(4) . . . . ?
O1A C6 O1B C9B -49.3(4) . . . . ?
C7 C6 O1B C9B -4.4(6) . . . . ?
C8B C9B O1B C6 -15.7(8) . . . . ?
C10B C9B O1B C6 109.2(6) . . . . ?
N7 C18 C19 N9 179.98(16) . . . . ?
N8 C18 C19 N9 -0.03(19) . . . . ?
N7 C18 C19 C20 -2.6(3) . . . . ?
N8 C18 C19 C20 177.39(15) . . . . ?
N9 C19 C20 N6 179.01(17) . . . . ?
C18 C19 C20 N6 2.2(2) . . . . ?
N9 C19 C20 N10 -3.8(3) . . . . ?
C18 C19 C20 N10 179.41(16) . . . . ?
O4 C22 C23 C24 -12.21(18) . . . . ?
N8 C22 C23 C24 107.12(17) . . . . ?
C22 C23 C24 O5 149.97(15) . . . . ?
C22 C23 C24 C25 31.22(17) . . . . ?
O5 C24 C25 O4 -160.89(16) . . . . ?
C23 C24 C25 O4 -39.73(18) . . . . ?
O5 C24 C25 C26 79.5(2) . . . . ?
C23 C24 C25 C26 -159.29(16) . . . . ?
O4 C25 C26 O6 72.1(2) . . . . ?
C24 C25 C26 O6 -171.88(16) . . . . ?
N9 C21 C27 C32 33.6(2) . . . . ?
N8 C21 C27 C32 -146.78(17) . . . . ?
N9 C21 C27 C28 -141.23(19) . . . . ?
N8 C21 C27 C28 38.4(3) . . . . ?
C32 C27 C28 C29 0.2(3) . . . . ?
C21 C27 C28 C29 174.89(18) . . . . ?
C27 C28 C29 C30 -0.6(3) . . . . ?
C28 C29 C30 C31 0.6(4) . . . . ?
C29 C30 C31 C32 -0.2(4) . . . . ?
C30 C31 C32 C27 -0.2(3) . . . . ?
C28 C27 C32 C31 0.2(3) . . . . ?
C21 C27 C32 C31 -174.85(18) . . . . ?
N10 C20 N6 C17 -177.56(17) . . . . ?
C19 C20 N6 C17 -0.2(2) . . . . ?
N7 C17 N6 C20 -1.9(3) . . . . ?
N6 C17 N7 C18 1.6(3) . . . . ?
N8 C18 N7 C17 -179.22(17) . . . . ?
C19 C18 N7 C17 0.8(2) . . . . ?
N7 C18 N8 C21 179.66(17) . . . . ?
C19 C18 N8 C21 -0.33(18) . . . . ?
N7 C18 N8 C22 1.4(3) . . . . ?
C19 C18 N8 C22 -178.57(15) . . . . ?
N9 C21 N8 C18 0.62(19) . . . . ?
C27 C21 N8 C18 -179.05(16) . . . . ?
N9 C21 N8 C22 178.92(15) . . . . ?
C27 C21 N8 C22 -0.7(3) . . . . ?
O4 C22 N8 C18 85.83(19) . . . . ?
C23 C22 N8 C18 -32.6(2) . . . . ?
O4 C22 N8 C21 -92.07(19) . . . . ?
C23 C22 N8 C21 149.55(16) . . . . ?
N8 C21 N9 C19 -0.62(19) . . . . ?
C27 C21 N9 C19 179.06(15) . . . . ?
C18 C19 N9 C21 0.40(19) . . . . ?
C20 C19 N9 C21 -176.59(18) . . . . ?
C26 C25 O4 C22 156.27(15) . . . . ?
C24 C25 O4 C22 33.74(19) . . . . ?
N8 C22 O4 C25 -137.24(14) . . . . ?
C23 C22 O4 C25 -13.33(19) . . . . ?
