#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/47/4024784.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_4024784
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(C20 H19 N5 O3), C H4 O, H2 O'
_chemical_formula_sum            'C41 H44 N10 O8'
_chemical_formula_weight         804.86
_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_date
;
'Thu Jul 24 16:10:21 2008'
;
_audit_creation_method
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET)
(compiled Apr 21 2008,18:23:10)
;
_cell_angle_alpha                93.768(2)
_cell_angle_beta                 94.058(3)
_cell_angle_gamma                101.822(3)
_cell_formula_units_Z            1
_cell_length_a                   7.8036(3)
_cell_length_b                   10.1562(3)
_cell_length_c                   12.3581(3)
_cell_measurement_reflns_used    7646
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      70.3344
_cell_measurement_theta_min      5.4957
_cell_volume                     953.03(5)
_computing_cell_refinement
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET)
(compiled Apr 21 2008,18:23:10)
;
_computing_data_collection
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET)
(compiled Apr 21 2008,18:23:10)
;
_computing_data_reduction
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET)
(compiled Apr 21 2008,18:23:10)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 8.2707
_diffrn_measured_fraction_theta_full 0.957
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_details
;
  1 omega  -42.00   11.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -13.7937   45.0000  300.0000    0.0000    0.0000 53

  2 omega  -38.00   14.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -13.7937  -45.0000  330.0000    0.0000    0.0000 52

  3 omega  -38.00   15.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -13.7937  -45.0000   60.0000    0.0000    0.0000 53

  4 omega   13.00   73.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -13.7937    0.0000   30.0000    0.0000    0.0000 60

  5 omega  -20.00   38.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       13.7937   77.0000  300.0000    0.0000    0.0000 58

  6 omega   35.00   87.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       13.7937   45.0000  330.0000    0.0000    0.0000 52

  7 omega  -53.00  -15.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -       13.7937  -45.0000  120.0000    0.0000    0.0000 38

  8 omega -127.00  -14.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -93.0000   77.0000  270.0000    0.0000    0.0000 113

  9 omega  -72.00  -19.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -93.0000   45.0000  180.0000    0.0000    0.0000 53

 10 omega -178.00   -6.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -93.0000    0.0000  300.0000    0.0000    0.0000 172

 11 omega -126.00  -68.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -93.0000   77.0000    0.0000    0.0000    0.0000 58

 12 omega -127.00  -17.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      -93.0000   77.0000   90.0000    0.0000    0.0000 110

 13 omega   75.00  128.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      100.0000  -45.0000   90.0000    0.0000    0.0000 53

 14 omega   76.00  134.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      100.0000  -77.0000  270.0000    0.0000    0.0000 58

 15 omega  121.00  167.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      100.0000   45.0000  300.0000    0.0000    0.0000 46

 16 omega   26.00   79.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      100.0000  -45.0000  330.0000    0.0000    0.0000 53

 17 omega   29.00   79.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      100.0000  -45.0000  270.0000    0.0000    0.0000 50

 18 omega   78.00  115.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      100.0000 -111.0000   58.0000    0.0000    0.0000 37

 19 omega   86.00  113.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      100.0000 -115.0000  252.0000    0.0000    0.0000 27

 20 omega   23.00  108.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      100.0000 -118.0000  143.0000    0.0000    0.0000 85

 21 omega   73.00  117.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      100.0000   45.0000   90.0000    0.0000    0.0000 44

 22 omega  143.00  170.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      100.0000   45.0000   60.0000    0.0000    0.0000 27

 23 omega   72.00  106.00   1.0000    6.0000
omega____ theta____ kappa____ phi______ omega'___ theta'___ frames
    -      100.0000   77.0000  240.0000    0.0000    0.0000 34

;
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'Phi & Omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Cu) X-ray Source'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0153
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            7241
_diffrn_reflns_theta_full        70.50
_diffrn_reflns_theta_max         70.50
_diffrn_reflns_theta_min         5.50
_exptl_absorpt_coefficient_mu    0.826
_exptl_absorpt_correction_T_max  0.900
_exptl_absorpt_correction_T_min  0.692
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET)
(compiled Apr 21 2008,18:23:10)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.75
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.09(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     577
_refine_ls_number_reflns         4386
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0333
_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)+(0.0771P)²+0.1321P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0925
_refine_ls_wR_factor_ref         0.0929
_reflns_number_gt                4345
_reflns_number_total             4386
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo9012282_si_002_4.cif
_cod_data_source_block           ijf0830
_cod_database_code               4024784
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 1.0829(3) -0.0091(2) 0.96422(19) 0.0230(4) Uani 1 1 d . . .
H1 H 1.1152 -0.0788 1.0005 0.028 Uiso 1 1 calc R . .
C2 C 0.8925(3) 0.0663(2) 0.85539(17) 0.0172(4) Uani 1 1 d . . .
C3 C 0.9983(3) 0.1934(2) 0.86241(16) 0.0170(4) Uani 1 1 d . . .
C4 C 1.1592(3) 0.2149(2) 0.92783(16) 0.0179(4) Uani 1 1 d . . .
C5 C 0.7704(2) 0.2045(2) 0.75926(16) 0.0156(4) Uani 1 1 d . . .
C6 C 0.5952(2) -0.0372(2) 0.75338(16) 0.0170(4) Uani 1 1 d . . .
H6 H 0.5173 -0.0060 0.6997 0.020 Uiso 1 1 calc R . .
C7 C 0.6349(3) -0.1701(2) 0.70719(17) 0.0201(4) Uani 1 1 d . . .
H7A H 0.6390 -0.1721 0.6288 0.024 Uiso 1 1 calc R . .
H7B H 0.7455 -0.1845 0.7401 0.024 Uiso 1 1 calc R . .
C8 C 0.4806(3) -0.2743(2) 0.73808(17) 0.0204(4) Uani 1 1 d . . .
H8 H 0.5142 -0.3607 0.7487 0.024 Uiso 1 1 calc R . .
C9 C 0.4339(3) -0.2102(2) 0.84522(18) 0.0226(4) Uani 1 1 d . . .
H9 H 0.3057 -0.2252 0.8448 0.027 Uiso 1 1 calc R . .
C10 C 0.5060(3) -0.2641(2) 0.94638(19) 0.0289(5) Uani 1 1 d . . .
H10A H 0.4970 -0.2043 1.0093 0.035 Uiso 1 1 calc R . .
H10B H 0.4340 -0.3519 0.9554 0.035 Uiso 1 1 calc R . .
C11 C 0.6366(3) 0.2608(2) 0.69665(16) 0.0169(4) Uani 1 1 d . . .
C12 C 0.6842(3) 0.3497(2) 0.61371(16) 0.0187(4) Uani 1 1 d . . .
C13 C 0.8522(3) 0.3735(2) 0.57294(18) 0.0248(5) Uani 1 1 d . . .
H13 H 0.9369 0.3288 0.5997 0.030 Uiso 1 1 calc R . .
C14 C 0.8910(3) 0.4614(3) 0.4947(2) 0.0342(6) Uani 1 1 d . . .
H14 H 1.0013 0.4747 0.4681 0.041 Uiso 1 1 calc R . .
C15 C 0.7665(4) 0.5323(3) 0.4536(2) 0.0363(6) Uani 1 1 d . . .
H15 H 0.7962 0.5941 0.4022 0.044 Uiso 1 1 calc R . .
C16 C 0.6029(3) 0.5102(2) 0.48906(19) 0.0283(5) Uani 1 1 d . . .
H16 H 0.5211 0.5570 0.4615 0.034 Uiso 1 1 calc R . .
C17 C 0.5553(3) 0.4164(2) 0.56781(17) 0.0205(4) Uani 1 1 d . . .
C18 C 0.3827(3) 0.3873(2) 0.60090(18) 0.0224(4) Uani 1 1 d . . .
H18 H 0.2983 0.4298 0.5703 0.027 Uiso 1 1 calc R . .
C19 C 0.3385(3) 0.2979(2) 0.67707(18) 0.0227(4) Uani 1 1 d . . .
H19 H 0.2235 0.2776 0.6962 0.027 Uiso 1 1 calc R . .
C20 C 0.4663(3) 0.2361(2) 0.72696(17) 0.0200(4) Uani 1 1 d . . .
H20 H 0.4358 0.1780 0.7809 0.024 Uiso 1 1 calc R . .
N1 N 1.1997(2) 0.1089(2) 0.97652(14) 0.0207(4) Uani 1 1 d . . .
N2 N 0.9267(2) -0.03968(18) 0.90690(15) 0.0211(4) Uani 1 1 d . . .
N3 N 0.7463(2) 0.07264(17) 0.78677(14) 0.0172(3) Uani 1 1 d . . .
N4 N 0.9218(2) 0.27906(18) 0.80157(14) 0.0176(3) Uani 1 1 d . . .
N5 N 1.2712(2) 0.33496(19) 0.94368(16) 0.0211(4) Uani 1 1 d . . .
H5A H 1.249(4) 0.403(4) 0.901(3) 0.039(8) Uiso 1 1 d . . .
H5B H 1.374(4) 0.330(3) 0.973(2) 0.020(6) Uiso 1 1 d . . .
O1 O 0.50469(19) -0.06699(15) 0.84685(13) 0.0223(3) Uani 1 1 d . . .
O2 O 0.3398(2) -0.28948(16) 0.65514(13) 0.0251(3) Uani 1 1 d . . .
H2 H 0.247(6) -0.353(5) 0.676(3) 0.063(11) Uiso 1 1 d . . .
O3 O 0.6827(2) -0.27641(17) 0.94355(14) 0.0303(4) Uani 1 1 d . . .
H3 H 0.744(4) -0.194(4) 0.929(3) 0.045(9) Uiso 1 1 d . . .
C21 C -0.2494(3) 0.4554(2) 0.05009(18) 0.0225(4) Uani 1 1 d . . .
H21 H -0.2884 0.5256 0.0183 0.027 Uiso 1 1 calc R . .
C22 C -0.0458(2) 0.3813(2) 0.14904(16) 0.0173(4) Uani 1 1 d . . .
C23 C -0.1458(3) 0.2519(2) 0.14007(17) 0.0166(4) Uani 1 1 d . . .
C24 C -0.3107(3) 0.2281(2) 0.07881(16) 0.0169(4) Uani 1 1 d . . .
C25 C 0.0835(3) 0.2462(2) 0.24401(16) 0.0167(4) Uani 1 1 d . . .
C26 C 0.2379(2) 0.4943(2) 0.25957(17) 0.0174(4) Uani 1 1 d . . .
H26 H 0.3209 0.4654 0.3114 0.021 Uiso 1 1 calc R . .
C27 C 0.3388(3) 0.5747(2) 0.17638(18) 0.0221(4) Uani 1 1 d . . .
H27A H 0.2650 0.5741 0.1097 0.027 Uiso 1 1 calc R . .
H27B H 0.4413 0.5396 0.1595 0.027 Uiso 1 1 calc R . .
C28 C 0.3913(3) 0.7158(2) 0.23443(18) 0.0217(4) Uani 1 1 d . . .
H28 H 0.4007 0.7846 0.1819 0.026 Uiso 1 1 calc R . .
C29 C 0.2390(3) 0.7223(2) 0.30471(17) 0.0215(4) Uani 1 1 d . . .
H29 H 0.2872 0.7641 0.3772 0.026 Uiso 1 1 calc R . .
C30 C 0.1076(3) 0.7998(2) 0.25925(19) 0.0273(5) Uani 1 1 d . . .
H30A H 0.0071 0.7866 0.3023 0.033 Uiso 1 1 calc R . .
H30B H 0.1612 0.8953 0.2667 0.033 Uiso 1 1 calc R . .
C31 C 0.2152(3) 0.1958(2) 0.31241(17) 0.0184(4) Uani 1 1 d . . .
C32 C 0.1622(3) 0.1203(2) 0.40189(16) 0.0179(4) Uani 1 1 d . . .
C33 C -0.0067(3) 0.1062(2) 0.44100(18) 0.0248(5) Uani 1 1 d . . .
H33 H -0.0874 0.1511 0.4092 0.030 Uiso 1 1 calc R . .
C34 C -0.0530(3) 0.0284(3) 0.5238(2) 0.0334(6) Uani 1 1 d . . .
H34 H -0.1634 0.0229 0.5492 0.040 Uiso 1 1 calc R . .
C35 C 0.0657(3) -0.0448(3) 0.5722(2) 0.0328(5) Uani 1 1 d . . .
H35 H 0.0316 -0.1008 0.6269 0.039 Uiso 1 1 calc R . .
C36 C 0.2294(3) -0.0318(2) 0.53746(19) 0.0277(5) Uani 1 1 d . . .
H36 H 0.3069 -0.0795 0.5691 0.033 Uiso 1 1 calc R . .
C37 C 0.2845(3) 0.0524(2) 0.45462(17) 0.0211(4) Uani 1 1 d . . .
C38 C 0.4561(3) 0.0687(2) 0.41973(19) 0.0261(5) Uani 1 1 d . . .
H38 H 0.5362 0.0249 0.4535 0.031 Uiso 1 1 calc R . .
C39 C 0.5056(3) 0.1474(3) 0.33769(19) 0.0284(5) Uani 1 1 d . . .
H39 H 0.6203 0.1599 0.3179 0.034 Uiso 1 1 calc R . .
C40 C 0.3837(3) 0.2101(2) 0.28258(18) 0.0233(4) Uani 1 1 d . . .
H40 H 0.4178 0.2618 0.2254 0.028 Uiso 1 1 calc R . .
N6 N -0.3604(2) 0.33470(18) 0.03529(15) 0.0209(4) Uani 1 1 d . . .
N7 N -0.0904(2) 0.48806(18) 0.10443(16) 0.0224(4) Uani 1 1 d . . .
N8 N 0.1038(2) 0.37723(17) 0.21492(14) 0.0167(3) Uani 1 1 d . . .
N9 N -0.0647(2) 0.16817(17) 0.20004(13) 0.0161(3) Uani 1 1 d . . .
N10 N -0.4184(2) 0.10765(19) 0.06463(16) 0.0210(4) Uani 1 1 d . . .
H10C H -0.388(4) 0.041(3) 0.089(2) 0.026(7) Uiso 1 1 d . . .
H10D H -0.529(4) 0.095(3) 0.028(2) 0.030(7) Uiso 1 1 d . . .
O4 O 0.15056(18) 0.58443(15) 0.31491(12) 0.0218(3) Uani 1 1 d . . .
O5 O 0.5510(2) 0.73253(18) 0.30261(14) 0.0291(4) Uani 1 1 d . . .
H5 H 0.633(5) 0.786(4) 0.265(3) 0.051(10) Uiso 1 1 d . . .
O6 O 0.0477(2) 0.76075(16) 0.14797(13) 0.0255(3) Uani 1 1 d . . .
H6A H 0.009(4) 0.667(4) 0.143(3) 0.034(7) Uiso 1 1 d . . .
O7 O 0.7590(2) 0.89710(17) 0.17185(14) 0.0251(3) Uani 1 1 d . . .
H7C H 0.831(4) 0.971(4) 0.191(3) 0.030(7) Uiso 1 1 d . . .
H7D H 0.834(6) 0.850(5) 0.147(4) 0.072(13) Uiso 1 1 d . . .
C41 C 0.9756(4) 0.6179(3) 0.8174(3) 0.0485(8) Uani 1 1 d . . .
H41A H 0.9856 0.6342 0.8952 0.073 Uiso 1 1 calc R . .
H41B H 0.8602 0.5664 0.7931 0.073 Uiso 1 1 calc R . .
H41C H 0.9945 0.7025 0.7850 0.073 Uiso 1 1 calc R . .
O8 O 1.1032(2) 0.54473(17) 0.78606(15) 0.0299(4) Uani 1 1 d . . .
H8A H 1.054(4) 0.461(3) 0.783(2) 0.026(7) Uiso 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
N2 C1 N1 128.6(2) . . ?
N2 C1 H1 115.7 . . ?
N1 C1 H1 115.7 . . ?
N2 C2 C3 125.92(19) . . ?
N2 C2 N3 128.47(19) . . ?
C3 C2 N3 105.60(18) . . ?
C2 C3 N4 111.01(18) . . ?
C2 C3 C4 117.40(19) . . ?
N4 C3 C4 131.6(2) . . ?
N5 C4 N1 119.18(19) . . ?
N5 C4 C3 123.1(2) . . ?
N1 C4 C3 117.73(19) . . ?
N4 C5 N3 112.52(17) . . ?
N4 C5 C11 122.76(18) . . ?
N3 C5 C11 124.54(17) . . ?
O1 C6 N3 107.21(15) . . ?
O1 C6 C7 106.37(17) . . ?
N3 C6 C7 116.64(16) . . ?
O1 C6 H6 108.8 . . ?
N3 C6 H6 108.8 . . ?
C7 C6 H6 108.8 . . ?
C8 C7 C6 102.62(16) . . ?
C8 C7 H7A 111.2 . . ?
C6 C7 H7A 111.2 . . ?
C8 C7 H7B 111.2 . . ?
C6 C7 H7B 111.2 . . ?
H7A C7 H7B 109.2 . . ?
O2 C8 C7 108.68(17) . . ?
O2 C8 C9 111.10(17) . . ?
C7 C8 C9 103.24(16) . . ?
O2 C8 H8 111.2 . . ?
C7 C8 H8 111.2 . . ?
C9 C8 H8 111.2 . . ?
O1 C9 C10 109.61(18) . . ?
O1 C9 C8 106.45(16) . . ?
C10 C9 C8 114.12(18) . . ?
O1 C9 H9 108.8 . . ?
C10 C9 H9 108.8 . . ?
C8 C9 H9 108.8 . . ?
O3 C10 C9 113.64(19) . . ?
O3 C10 H10A 108.8 . . ?
C9 C10 H10A 108.8 . . ?
O3 C10 H10B 108.8 . . ?
C9 C10 H10B 108.8 . . ?
H10A C10 H10B 107.7 . . ?
C20 C11 C12 119.88(19) . . ?
C20 C11 C5 118.62(19) . . ?
C12 C11 C5 121.21(17) . . ?
C13 C12 C17 118.07(19) . . ?
C13 C12 C11 123.42(19) . . ?
C17 C12 C11 118.50(18) . . ?
C14 C13 C12 120.7(2) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 121.0(2) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C16 C15 C14 120.0(2) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C16 C17 120.8(2) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C18 C17 C16 121.2(2) . . ?
C18 C17 C12 119.51(19) . . ?
C16 C17 C12 119.3(2) . . ?
C19 C18 C17 120.84(19) . . ?
C19 C18 H18 119.6 . . ?
C17 C18 H18 119.6 . . ?
C18 C19 C20 120.35(19) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C11 C20 C19 120.8(2) . . ?
C11 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C1 N1 C4 118.62(18) . . ?
C1 N2 C2 111.63(18) . . ?
C5 N3 C2 106.07(16) . . ?
C5 N3 C6 127.14(17) . . ?
C2 N3 C6 126.77(17) . . ?
C5 N4 C3 104.76(17) . . ?
C4 N5 H5A 117(2) . . ?
C4 N5 H5B 113.1(18) . . ?
H5A N5 H5B 125(3) . . ?
C6 O1 C9 110.54(15) . . ?
C8 O2 H2 107(2) . . ?
C10 O3 H3 106(2) . . ?
N7 C21 N6 128.6(2) . . ?
N7 C21 H21 115.7 . . ?
N6 C21 H21 115.7 . . ?
N7 C22 C23 125.91(19) . . ?
N7 C22 N8 128.43(19) . . ?
C23 C22 N8 105.64(18) . . ?
C22 C23 N9 110.91(18) . . ?
C22 C23 C24 117.57(19) . . ?
N9 C23 C24 131.44(19) . . ?
N10 C24 N6 119.40(19) . . ?
N10 C24 C23 122.97(19) . . ?
N6 C24 C23 117.62(19) . . ?
N9 C25 N8 112.47(17) . . ?
N9 C25 C31 123.03(18) . . ?
N8 C25 C31 124.44(18) . . ?
O4 C26 N8 107.16(15) . . ?
O4 C26 C27 105.87(17) . . ?
N8 C26 C27 115.54(17) . . ?
O4 C26 H26 109.4 . . ?
N8 C26 H26 109.4 . . ?
C27 C26 H26 109.4 . . ?
C26 C27 C28 102.59(16) . . ?
C26 C27 H27A 111.2 . . ?
C28 C27 H27A 111.2 . . ?
C26 C27 H27B 111.2 . . ?
C28 C27 H27B 111.2 . . ?
H27A C27 H27B 109.2 . . ?
O5 C28 C27 111.69(18) . . ?
O5 C28 C29 109.60(17) . . ?
C27 C28 C29 102.98(16) . . ?
O5 C28 H28 110.8 . . ?
C27 C28 H28 110.8 . . ?
C29 C28 H28 110.8 . . ?
O4 C29 C30 109.30(16) . . ?
O4 C29 C28 106.77(16) . . ?
C30 C29 C28 114.50(18) . . ?
O4 C29 H29 108.7 . . ?
C30 C29 H29 108.7 . . ?
C28 C29 H29 108.7 . . ?
O6 C30 C29 113.79(17) . . ?
O6 C30 H30A 108.8 . . ?
C29 C30 H30A 108.8 . . ?
O6 C30 H30B 108.8 . . ?
C29 C30 H30B 108.8 . . ?
H30A C30 H30B 107.7 . . ?
C40 C31 C32 120.35(19) . . ?
C40 C31 C25 119.6(2) . . ?
C32 C31 C25 119.73(17) . . ?
C33 C32 C31 123.78(18) . . ?
C33 C32 C37 117.73(19) . . ?
C31 C32 C37 118.49(18) . . ?
C34 C33 C32 121.4(2) . . ?
C34 C33 H33 119.3 . . ?
C32 C33 H33 119.3 . . ?
C33 C34 C35 120.8(2) . . ?
C33 C34 H34 119.6 . . ?
C35 C34 H34 119.6 . . ?
C36 C35 C34 119.2(2) . . ?
C36 C35 H35 120.4 . . ?
C34 C35 H35 120.4 . . ?
C35 C36 C37 121.6(2) . . ?
C35 C36 H36 119.2 . . ?
C37 C36 H36 119.2 . . ?
C36 C37 C38 121.8(2) . . ?
C36 C37 C32 119.2(2) . . ?
C38 C37 C32 118.9(2) . . ?
C39 C38 C37 121.1(2) . . ?
C39 C38 H38 119.4 . . ?
C37 C38 H38 119.4 . . ?
C38 C39 C40 120.2(2) . . ?
C38 C39 H39 119.9 . . ?
C40 C39 H39 119.9 . . ?
C31 C40 C39 120.8(2) . . ?
C31 C40 H40 119.6 . . ?
C39 C40 H40 119.6 . . ?
C21 N6 C24 118.52(18) . . ?
C21 N7 C22 111.73(19) . . ?
C25 N8 C22 106.13(16) . . ?
C25 N8 C26 127.38(17) . . ?
C22 N8 C26 125.60(17) . . ?
C25 N9 C23 104.82(17) . . ?
C24 N10 H10C 120(2) . . ?
C24 N10 H10D 121.9(19) . . ?
H10C N10 H10D 118(3) . . ?
C26 O4 C29 109.84(15) . . ?
C28 O5 H5 104(2) . . ?
C30 O6 H6A 106.2(19) . . ?
H7C O7 H7D 98(3) . . ?
O8 C41 H41A 109.5 . . ?
O8 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
O8 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C41 O8 H8A 106.5(19) . . ?
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 1.341(3) . ?
C1 H1 0.9300 . ?
C2 N2 1.349(3) . ?
C2 C3 1.376(3) . ?
C2 N3 1.387(3) . ?
C3 N4 1.383(3) . ?
C3 C4 1.414(3) . ?
C4 N5 1.340(3) . ?
C4 N1 1.349(3) . ?
C5 N4 1.318(3) . ?
C5 N3 1.382(3) . ?
C5 C11 1.485(3) . ?
C6 O1 1.414(2) . ?
C6 N3 1.462(3) . ?
C6 C7 1.529(3) . ?
C6 H6 0.9800 . ?
C7 C8 1.521(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O2 1.425(3) . ?
C8 C9 1.537(3) . ?
C8 H8 0.9800 . ?
C9 O1 1.444(3) . ?
C9 C10 1.515(3) . ?
C9 H9 0.9800 . ?
C10 O3 1.412(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C20 1.384(3) . ?
C11 C12 1.429(3) . ?
C12 C13 1.418(3) . ?
C12 C17 1.429(3) . ?
C13 C14 1.367(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.409(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.359(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.421(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.414(3) . ?
C18 C19 1.364(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.410(3) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
N5 H5A 0.93(4) . ?
N5 H5B 0.87(3) . ?
O2 H2 0.93(5) . ?
O3 H3 0.91(4) . ?
C21 N7 1.336(3) . ?
C21 N6 1.341(3) . ?
C21 H21 0.9300 . ?
C22 N7 1.344(3) . ?
C22 C23 1.378(3) . ?
C22 N8 1.385(3) . ?
C23 N9 1.382(3) . ?
C23 C24 1.413(3) . ?
C24 N10 1.328(3) . ?
C24 N6 1.353(3) . ?
C25 N9 1.319(3) . ?
C25 N8 1.382(3) . ?
C25 C31 1.478(3) . ?
C26 O4 1.418(2) . ?
C26 N8 1.462(2) . ?
C26 C27 1.518(3) . ?
C26 H26 0.9800 . ?
C27 C28 1.523(3) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C28 O5 1.428(3) . ?
C28 C29 1.530(3) . ?
C28 H28 0.9800 . ?
C29 O4 1.446(2) . ?
C29 C30 1.515(3) . ?
C29 H29 0.9800 . ?
C30 O6 1.424(3) . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C31 C40 1.372(3) . ?
C31 C32 1.424(3) . ?
C32 C33 1.419(3) . ?
C32 C37 1.433(3) . ?
C33 C34 1.357(3) . ?
C33 H33 0.9300 . ?
C34 C35 1.425(4) . ?
C34 H34 0.9300 . ?
C35 C36 1.360(4) . ?
C35 H35 0.9300 . ?
C36 C37 1.411(3) . ?
C36 H36 0.9300 . ?
C37 C38 1.417(3) . ?
C38 C39 1.361(4) . ?
C38 H38 0.9300 . ?
C39 C40 1.410(3) . ?
C39 H39 0.9300 . ?
C40 H40 0.9300 . ?
N10 H10C 0.83(3) . ?
N10 H10D 0.93(3) . ?
O5 H5 0.92(4) . ?
O6 H6A 0.93(3) . ?
O7 H7C 0.85(3) . ?
O7 H7D 0.89(5) . ?
C41 O8 1.419(3) . ?
C41 H41A 0.9600 . ?
C41 H41B 0.9600 . ?
C41 H41C 0.9600 . ?
O8 H8A 0.85(3) . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O8 H8A N4 0.85(3) 1.96(3) 2.804(2) 169(3) .
O7 H7D O6 0.89(5) 2.05(5) 2.898(2) 158(4) 1_655
O7 H7C N9 0.85(3) 1.99(4) 2.801(2) 159(3) 1_665
O6 H6A N7 0.93(3) 1.84(4) 2.760(2) 168(3) .
O5 H5 O7 0.92(4) 1.86(4) 2.767(2) 168(3) .
N10 H10D N1 0.93(3) 2.20(3) 3.102(3) 163(3) 1_354
N10 H10C O7 0.83(3) 2.28(3) 3.094(3) 165(3) 1_445
O3 H3 N2 0.91(4) 1.94(4) 2.829(3) 165(3) .
O2 H2 O8 0.93(5) 2.03(5) 2.893(2) 154(4) 1_445
N5 H5B N6 0.87(3) 2.15(3) 3.015(3) 174(3) 1_756
N5 H5A O8 0.93(4) 2.47(4) 3.373(3) 163(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_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 -178.42(19) . . . . ?
N3 C2 C3 N4 0.8(2) . . . . ?
N2 C2 C3 C4 1.2(3) . . . . ?
N3 C2 C3 C4 -179.58(16) . . . . ?
C2 C3 C4 N5 -178.04(18) . . . . ?
N4 C3 C4 N5 1.5(3) . . . . ?
C2 C3 C4 N1 1.6(3) . . . . ?
N4 C3 C4 N1 -178.86(19) . . . . ?
O1 C6 C7 C8 31.2(2) . . . . ?
N3 C6 C7 C8 150.70(17) . . . . ?
C6 C7 C8 O2 86.81(19) . . . . ?
C6 C7 C8 C9 -31.2(2) . . . . ?
O2 C8 C9 O1 -94.92(19) . . . . ?
C7 C8 C9 O1 21.4(2) . . . . ?
O2 C8 C9 C10 144.05(18) . . . . ?
C7 C8 C9 C10 -99.6(2) . . . . ?
O1 C9 C10 O3 -74.9(2) . . . . ?
C8 C9 C10 O3 44.4(3) . . . . ?
N4 C5 C11 C20 -127.3(2) . . . . ?
N3 C5 C11 C20 47.5(3) . . . . ?
N4 C5 C11 C12 46.5(3) . . . . ?
N3 C5 C11 C12 -138.6(2) . . . . ?
C20 C11 C12 C13 -175.7(2) . . . . ?
C5 C11 C12 C13 10.5(3) . . . . ?
C20 C11 C12 C17 3.1(3) . . . . ?
C5 C11 C12 C17 -170.73(17) . . . . ?
C17 C12 C13 C14 2.2(3) . . . . ?
C11 C12 C13 C14 -179.0(2) . . . . ?
C12 C13 C14 C15 1.0(4) . . . . ?
C13 C14 C15 C16 -2.3(4) . . . . ?
C14 C15 C16 C17 0.2(4) . . . . ?
C15 C16 C17 C18 -176.5(2) . . . . ?
C15 C16 C17 C12 3.0(4) . . . . ?
C13 C12 C17 C18 175.39(19) . . . . ?
C11 C12 C17 C18 -3.5(3) . . . . ?
C13 C12 C17 C16 -4.2(3) . . . . ?
C11 C12 C17 C16 177.0(2) . . . . ?
C16 C17 C18 C19 -179.5(2) . . . . ?
C12 C17 C18 C19 0.9(3) . . . . ?
C17 C18 C19 C20 2.1(3) . . . . ?
C12 C11 C20 C19 -0.1(3) . . . . ?
C5 C11 C20 C19 173.85(18) . . . . ?
C18 C19 C20 C11 -2.6(3) . . . . ?
N2 C1 N1 C4 1.4(3) . . . . ?
N5 C4 N1 C1 176.90(18) . . . . ?
C3 C4 N1 C1 -2.7(3) . . . . ?
N1 C1 N2 C2 1.3(3) . . . . ?
C3 C2 N2 C1 -2.5(3) . . . . ?
N3 C2 N2 C1 178.5(2) . . . . ?
N4 C5 N3 C2 2.4(2) . . . . ?
C11 C5 N3 C2 -172.92(17) . . . . ?
N4 C5 N3 C6 -179.37(17) . . . . ?
C11 C5 N3 C6 5.3(3) . . . . ?
N2 C2 N3 C5 177.34(19) . . . . ?
C3 C2 N3 C5 -1.8(2) . . . . ?
N2 C2 N3 C6 -0.9(3) . . . . ?
C3 C2 N3 C6 179.95(17) . . . . ?
O1 C6 N3 C5 -110.3(2) . . . . ?
C7 C6 N3 C5 130.6(2) . . . . ?
O1 C6 N3 C2 67.5(2) . . . . ?
C7 C6 N3 C2 -51.5(3) . . . . ?
N3 C5 N4 C3 -1.9(2) . . . . ?
C11 C5 N4 C3 173.54(17) . . . . ?
C2 C3 N4 C5 0.7(2) . . . . ?
C4 C3 N4 C5 -178.9(2) . . . . ?
N3 C6 O1 C9 -143.92(16) . . . . ?
C7 C6 O1 C9 -18.5(2) . . . . ?
C10 C9 O1 C6 121.91(18) . . . . ?
C8 C9 O1 C6 -2.0(2) . . . . ?
N7 C22 C23 N9 -177.19(19) . . . . ?
N8 C22 C23 N9 1.2(2) . . . . ?
N7 C22 C23 C24 -0.2(3) . . . . ?
N8 C22 C23 C24 178.21(16) . . . . ?
C22 C23 C24 N10 -179.91(18) . . . . ?
N9 C23 C24 N10 -3.6(3) . . . . ?
C22 C23 C24 N6 -1.4(3) . . . . ?
N9 C23 C24 N6 174.85(19) . . . . ?
O4 C26 C27 C28 33.9(2) . . . . ?
N8 C26 C27 C28 152.32(17) . . . . ?
C26 C27 C28 O5 85.71(19) . . . . ?
C26 C27 C28 C29 -31.8(2) . . . . ?
O5 C28 C29 O4 -99.41(19) . . . . ?
C27 C28 C29 O4 19.6(2) . . . . ?
O5 C28 C29 C30 139.47(19) . . . . ?
C27 C28 C29 C30 -101.5(2) . . . . ?
O4 C29 C30 O6 -70.2(2) . . . . ?
C28 C29 C30 O6 49.5(2) . . . . ?
N9 C25 C31 C40 121.7(2) . . . . ?
N8 C25 C31 C40 -55.3(3) . . . . ?
N9 C25 C31 C32 -51.6(3) . . . . ?
N8 C25 C31 C32 131.4(2) . . . . ?
C40 C31 C32 C33 176.9(2) . . . . ?
C25 C31 C32 C33 -9.8(3) . . . . ?
C40 C31 C32 C37 -4.3(3) . . . . ?
C25 C31 C32 C37 168.97(18) . . . . ?
C31 C32 C33 C34 177.2(2) . . . . ?
C37 C32 C33 C34 -1.5(3) . . . . ?
C32 C33 C34 C35 -1.8(4) . . . . ?
C33 C34 C35 C36 2.7(4) . . . . ?
C34 C35 C36 C37 -0.1(4) . . . . ?
C35 C36 C37 C38 178.6(2) . . . . ?
C35 C36 C37 C32 -3.3(3) . . . . ?
C33 C32 C37 C36 4.0(3) . . . . ?
C31 C32 C37 C36 -174.83(19) . . . . ?
C33 C32 C37 C38 -177.79(19) . . . . ?
C31 C32 C37 C38 3.3(3) . . . . ?
C36 C37 C38 C39 178.2(2) . . . . ?
C32 C37 C38 C39 0.1(3) . . . . ?
C37 C38 C39 C40 -2.6(4) . . . . ?
C32 C31 C40 C39 1.8(3) . . . . ?
C25 C31 C40 C39 -171.4(2) . . . . ?
C38 C39 C40 C31 1.7(4) . . . . ?
N7 C21 N6 C24 -0.5(3) . . . . ?
N10 C24 N6 C21 -179.72(19) . . . . ?
C23 C24 N6 C21 1.7(3) . . . . ?
N6 C21 N7 C22 -1.0(3) . . . . ?
C23 C22 N7 C21 1.3(3) . . . . ?
N8 C22 N7 C21 -176.7(2) . . . . ?
N9 C25 N8 C22 1.2(2) . . . . ?
C31 C25 N8 C22 178.49(18) . . . . ?
N9 C25 N8 C26 170.81(17) . . . . ?
C31 C25 N8 C26 -11.9(3) . . . . ?
N7 C22 N8 C25 176.9(2) . . . . ?
C23 C22 N8 C25 -1.4(2) . . . . ?
N7 C22 N8 C26 7.1(3) . . . . ?
C23 C22 N8 C26 -171.25(17) . . . . ?
O4 C26 N8 C25 -114.0(2) . . . . ?
C27 C26 N8 C25 128.3(2) . . . . ?
O4 C26 N8 C22 53.7(2) . . . . ?
C27 C26 N8 C22 -64.0(2) . . . . ?
N8 C25 N9 C23 -0.4(2) . . . . ?
C31 C25 N9 C23 -177.79(18) . . . . ?
C22 C23 N9 C25 -0.5(2) . . . . ?
C24 C23 N9 C25 -177.0(2) . . . . ?
N8 C26 O4 C29 -146.21(16) . . . . ?
C27 C26 O4 C29 -22.4(2) . . . . ?
C30 C29 O4 C26 125.90(18) . . . . ?
C28 C29 O4 C26 1.5(2) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659028
