#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202017 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/11/7151160.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_7151160
loop_
_publ_author_name
'Vrábel, Milan'
'Pohl, Radek'
'Klepetárová, Blanka'
'Votruba, Ivan'
'Hocek, Michal'
_publ_section_title
;
 Synthesis of 2'-deoxyadenosine nucleosides bearing bipyridine-type
 ligands and their Ru-complexes in position 8 through cross-coupling
 reactions.
;
_journal_issue                   17
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2849
_journal_page_last               2857
_journal_paper_doi               10.1039/b709245h
_journal_volume                  5
_journal_year                    2007
_chemical_absolute_configuration unk
_chemical_formula_moiety         'C28 H23 N7 O3, C28 H22 N7 O3'
_chemical_formula_sum            'C28 H23 N7 O3'
_chemical_formula_weight         505.53
_chemical_name_common
8-((1'',10'''-phenantroline-2''-yl)phenyl)-2'-deoxyadenosine
_chemical_name_systematic
8-[(1'',10'''-phenantroline-2''-yl]phenyl]-2'-deoxyadenosine
_space_group_IT_number           1
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      1
_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
_audit_creation_date             07-06-15
_audit_creation_method           CRYSTALS_ver_12.84
_cell_angle_alpha                96.79(3)
_cell_angle_beta                 106.00(3)
_cell_angle_gamma                105.90(3)
_cell_formula_units_Z            2
_cell_length_a                   10.790(4)
_cell_length_b                   10.800(3)
_cell_length_c                   13.163(4)
_cell_measurement_reflns_used    0
_cell_measurement_temperature    150
_cell_measurement_theta_max      77
_cell_measurement_theta_min      4
_cell_volume                     1386.6(9)
_computing_cell_refinement       'CrysAlis RED, (Oxford Diffraction, 2002)'
_computing_data_collection       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis RED, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      150
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_device_type  'Oxford Diffraction XCALIBUR'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.056
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5801
_diffrn_reflns_theta_full        71.623
_diffrn_reflns_theta_max         77.851
_diffrn_reflns_theta_min         4.353
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.671
_exptl_absorpt_correction_T_max  0.89
_exptl_absorpt_correction_T_min  0.88
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
Analytical Absorption (De Meulenaer & Tompa, 1965)
;
_exptl_crystal_colour            'light yellow'
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_description       prism
_exptl_crystal_F_000             527
_exptl_crystal_size_max          0.63
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.17
_platon_squeeze_details
;
The methanol solvent molecules were not modelled and the disordered
density was taken into account using the SQUEEZE/PLATON procedure.
;
_refine_diff_density_max         0.43
_refine_diff_density_min         -0.26
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9870
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     685
_refine_ls_number_reflns         2973
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0894
_refine_ls_R_factor_gt           0.0576
_refine_ls_shift/su_max          0.003747
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982)
[weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)]
where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax
Method = Robust Weighting (Prince, 1982)
W = [weight] * [1-(deltaF/6*sigmaF)²]²
Ai are:
17.3 5.05 15.0
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.0920
_refine_ls_wR_factor_gt          0.0712
_refine_ls_wR_factor_ref         0.0712
_reflns_limit_h_max              12
_reflns_limit_h_min              -13
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              16
_reflns_limit_l_min              0
_reflns_number_gt                2973
_reflns_number_total             5801
_reflns_threshold_expression     I>2.0σ(I)
_cod_data_source_file            b709245h.txt
_cod_data_source_block           9c
_cod_original_cell_volume        1386.5(9)
_cod_database_code               7151160
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
O16 O -0.5637(6) -1.1453(5) -0.7703(4) 0.0720 1.0000 Uani . . . . . .
O17 O -0.5134(7) -1.0310(5) -0.4347(4) 0.0838 1.0000 Uani . . . . . .
O18 O -0.4420(7) -0.8872(6) -0.6210(6) 0.0785 1.0000 Uani . . . . . .
O54 O -0.7653(9) -0.3972(7) -0.7070(6) 0.1034 1.0000 Uani . . . . . .
O55 O -1.1376(8) -0.3957(6) -0.6188(6) 0.0930 1.0000 Uani . . . . . .
O56 O -0.9734(7) -0.6228(6) -0.6789(6) 0.0917 1.0000 Uani . . . . . .
N1 N -0.7290(6) -0.8534(6) -1.0016(5) 0.0507 1.0000 Uani . . . . . .
N3 N -0.6523(6) -0.9418(6) -0.8431(5) 0.0506 1.0000 Uani . . . . . .
N7 N -0.6107(7) -0.7922(6) -0.6768(5) 0.0533 1.0000 Uani . . . . . .
N9 N -0.6598(7) -0.6219(6) -0.7444(5) 0.0499 1.0000 Uani . . . . . .
N10 N -0.7517(6) -0.6454(6) -0.9907(5) 0.0493 1.0000 Uani . . . . . .
N25 N -0.4103(7) -0.2137(6) -0.2228(6) 0.0581 1.0000 Uani . . . . . .
N33 N -0.2178(8) 0.0346(7) -0.1733(8) 0.0762 1.0000 Uani . . . . . .
N39 N -0.8661(7) -0.6959(6) -0.2374(5) 0.0507 1.0000 Uani . . . . . .
N41 N -0.9614(7) -0.6169(6) -0.3927(5) 0.0553 1.0000 Uani . . . . . .
N45 N -1.0043(6) -0.7700(6) -0.5638(5) 0.0492 1.0000 Uani . . . . . .
N47 N -0.9244(7) -0.9240(6) -0.4919(5) 0.0553 1.0000 Uani . . . . . .
N48 N -0.8254(9) -0.8968(7) -0.2470(6) 0.0713 1.0000 Uani . . . . . .
N63 N -1.1740(6) -1.3247(6) -1.0185(5) 0.0508 1.0000 Uani . . . . . .
N71 N -1.3526(7) -1.5704(6) -1.0503(7) 0.0646 1.0000 Uani . . . . . .
C2 C -0.6939(8) -0.9441(8) -0.9485(7) 0.0531 1.0000 Uani . . . . . .
C4 C -0.6448(8) -0.8281(8) -0.7848(7) 0.0546 1.0000 Uani . . . . . .
C5 C -0.6758(7) -0.7239(7) -0.8261(6) 0.0460 1.0000 Uani . . . . . .
C6 C -0.7219(7) -0.7428(7) -0.9412(6) 0.0458 1.0000 Uani . . . . . .
C8 C -0.6189(7) -0.6636(7) -0.6571(6) 0.0486 1.0000 Uani . . . . . .
C11 C -0.5540(8) -0.8617(7) -0.5977(6) 0.0557 1.0000 Uani . . . . . .
C12 C -0.6512(9) -0.9911(7) -0.5969(6) 0.0670 1.0000 Uani . . . . . .
C13 C -0.5510(11) -1.0623(8) -0.5507(7) 0.0732 1.0000 Uani . . . . . .
C14 C -0.4280(11) -1.0062(10) -0.5896(7) 0.0794 1.0000 Uani . . . . . .
C15 C -0.4291(11) -1.0987(10) -0.6877(8) 0.0865 1.0000 Uani . . . . . .
C19 C -0.5860(8) -0.5829(8) -0.5478(5) 0.0503 1.0000 Uani . . . . . .
C20 C -0.6356(9) -0.6325(7) -0.4685(7) 0.0579 1.0000 Uani . . . . . .
C21 C -0.6042(8) -0.5530(8) -0.3658(6) 0.0544 1.0000 Uani . . . . . .
C22 C -0.5274(8) -0.4218(7) -0.3461(7) 0.0541 1.0000 Uani . . . . . .
C23 C -0.4790(8) -0.3707(8) -0.4279(7) 0.0562 1.0000 Uani . . . . . .
C24 C -0.5113(9) -0.4497(8) -0.5259(6) 0.0561 1.0000 Uani . . . . . .
C26 C -0.4979(8) -0.3302(8) -0.2407(6) 0.0516 1.0000 Uani . . . . . .
C27 C -0.5629(9) -0.3741(10) -0.1660(8) 0.0690 1.0000 Uani . . . . . .
C28 C -0.5371(11) -0.2846(11) -0.0737(7) 0.0751 1.0000 Uani . . . . . .
C29 C -0.4488(9) -0.1601(9) -0.0504(8) 0.0662 1.0000 Uani . . . . . .
C30 C -0.3819(7) -0.1261(8) -0.1267(8) 0.0630 1.0000 Uani . . . . . .
C31 C -0.4194(11) -0.0656(11) 0.0399(8) 0.0764 1.0000 Uani . . . . . .
C32 C -0.3373(13) 0.0485(13) 0.0608(8) 0.0907 1.0000 Uani . . . . . .
C34 C -0.1323(11) 0.1541(9) -0.1577(13) 0.1040 1.0000 Uani . . . . . .
C35 C -0.1051(13) 0.2507(10) -0.0597(14) 0.1086 1.0000 Uani . . . . . .
C36 C -0.1683(14) 0.2162(14) 0.0060(14) 0.1093 1.0000 Uani . . . . . .
C37 C -0.2577(10) 0.0924(9) -0.0124(9) 0.0760 1.0000 Uani . . . . . .
C38 C -0.2858(8) 0.0037(8) -0.1068(9) 0.0717 1.0000 Uani . . . . . .
C40 C -0.9110(8) -0.6093(7) -0.2878(6) 0.0521 1.0000 Uani . . . . . .
C42 C -0.9579(8) -0.7276(6) -0.4504(6) 0.0463 1.0000 Uani . . . . . .
C43 C -0.9138(9) -0.8246(7) -0.4092(6) 0.0532 1.0000 Uani . . . . . .
C44 C -0.8667(9) -0.8101(7) -0.2973(6) 0.0553 1.0000 Uani . . . . . .
C46 C -0.9786(9) -0.8876(7) -0.5835(7) 0.0567 1.0000 Uani . . . . . .
C49 C -1.0736(9) -0.7139(8) -0.6475(7) 0.0591 1.0000 Uani . . . . . .
C50 C -1.1580(10) -0.6340(10) -0.6181(8) 0.0738 1.0000 Uani . . . . . .
C51 C -1.0720(10) -0.4917(8) -0.6052(8) 0.0722 1.0000 Uani . . . . . .
C52 C -0.9774(12) -0.4966(9) -0.6730(7) 0.0787 1.0000 Uani . . . . . .
C53 C -0.8400(11) -0.4009(9) -0.6338(9) 0.0832 1.0000 Uani . . . . . .
C57 C -1.0025(8) -0.9631(6) -0.6914(7) 0.0508 1.0000 Uani . . . . . .
C58 C -0.9739(7) -0.9054(7) -0.7724(6) 0.0429 1.0000 Uani . . . . . .
C59 C -0.9975(8) -0.9815(7) -0.8716(6) 0.0492 1.0000 Uani . . . . . .
C60 C -1.0542(7) -1.1178(7) -0.8943(6) 0.0445 1.0000 Uani . . . . . .
C61 C -1.0812(8) -1.1765(7) -0.8103(6) 0.0508 1.0000 Uani . . . . . .
C62 C -1.0584(9) -1.0999(8) -0.7124(7) 0.0638 1.0000 Uani . . . . . .
C64 C -1.0892(7) -1.2003(7) -1.0024(6) 0.0478 1.0000 Uani . . . . . .
C65 C -1.0355(9) -1.1562(8) -1.0811(6) 0.0578 1.0000 Uani . . . . . .
C66 C -1.0631(8) -1.2420(9) -1.1783(7) 0.0618 1.0000 Uani . . . . . .
C67 C -1.1520(8) -1.3716(9) -1.1952(6) 0.0608 1.0000 Uani . . . . . .
C68 C -1.2065(8) -1.4083(7) -1.1142(6) 0.0510 1.0000 Uani . . . . . .
C69 C -1.1847(10) -1.4660(10) -1.2966(7) 0.0734 1.0000 Uani . . . . . .
C70 C -1.2716(9) -1.5912(9) -1.3129(8) 0.0696 1.0000 Uani . . . . . .
C72 C -1.4392(9) -1.6908(8) -1.0708(9) 0.0746 1.0000 Uani . . . . . .
C73 C -1.4774(10) -1.7852(9) -1.1677(9) 0.0759 1.0000 Uani . . . . . .
C74 C -1.4206(9) -1.7566(8) -1.2451(7) 0.0729 1.0000 Uani . . . . . .
C75 C -1.3278(10) -1.6295(9) -1.2316(8) 0.0732 1.0000 Uani . . . . . .
C76 C -1.2967(9) -1.5370(8) -1.1326(6) 0.0572 1.0000 Uani . . . . . .
H21 H -0.6990 -1.0211 -0.9930 0.0646 1.0000 Uiso R . . . . .
H111 H -0.5228 -0.8055 -0.5252 0.0680 1.0000 Uiso R . . . . .
H121 H -0.7104 -1.0361 -0.6692 0.0783 1.0000 Uiso R . . . . .
H122 H -0.7066 -0.9803 -0.5519 0.0780 1.0000 Uiso R . . . . .
H131 H -0.5924 -1.1578 -0.5774 0.0869 1.0000 Uiso R . . . . .
H141 H -0.3440 -0.9882 -0.5294 0.1001 1.0000 Uiso R . . . . .
H151 H -0.4070 -1.1750 -0.6649 0.1120 1.0000 Uiso R . . . . .
H152 H -0.3611 -1.0522 -0.7170 0.1120 1.0000 Uiso R . . . . .
H201 H -0.6918 -0.7202 -0.4846 0.0671 1.0000 Uiso R . . . . .
H211 H -0.6345 -0.5879 -0.3122 0.0628 1.0000 Uiso R . . . . .
H231 H -0.4262 -0.2831 -0.4150 0.0712 1.0000 Uiso R . . . . .
H241 H -0.4829 -0.4158 -0.5800 0.0698 1.0000 Uiso R . . . . .
H271 H -0.6217 -0.4602 -0.1791 0.0767 1.0000 Uiso R . . . . .
H281 H -0.5816 -0.3113 -0.0255 0.0922 1.0000 Uiso R . . . . .
H311 H -0.4629 -0.0884 0.0902 0.0828 1.0000 Uiso R . . . . .
H321 H -0.3257 0.1075 0.1241 0.1031 1.0000 Uiso R . . . . .
H341 H -0.0893 0.1766 -0.2086 0.1199 1.0000 Uiso R . . . . .
H351 H -0.0434 0.3348 -0.0459 0.1130 1.0000 Uiso R . . . . .
H361 H -0.1524 0.2771 0.0683 0.1221 1.0000 Uiso R . . . . .
H401 H -0.9053 -0.5326 -0.2432 0.0640 1.0000 Uiso R . . . . .
H491 H -1.1319 -0.7866 -0.7089 0.0686 1.0000 Uiso R . . . . .
H501 H -1.2418 -0.6494 -0.6771 0.0865 1.0000 Uiso R . . . . .
H502 H -1.1797 -0.6521 -0.5537 0.0855 1.0000 Uiso R . . . . .
H511 H -1.0094 -0.4630 -0.5292 0.0896 1.0000 Uiso R . . . . .
H521 H -1.0239 -0.4889 -0.7475 0.0936 1.0000 Uiso R . . . . .
H531 H -0.8488 -0.3136 -0.6178 0.1050 1.0000 Uiso R . . . . .
H532 H -0.7883 -0.4203 -0.5668 0.1048 1.0000 Uiso R . . . . .
H581 H -0.9383 -0.8140 -0.7617 0.0521 1.0000 Uiso R . . . . .
H591 H -0.9742 -0.9389 -0.9248 0.0612 1.0000 Uiso R . . . . .
H611 H -1.1151 -1.2680 -0.8205 0.0618 1.0000 Uiso R . . . . .
H621 H -1.0800 -1.1390 -0.6569 0.0737 1.0000 Uiso R . . . . .
H651 H -0.9808 -1.0681 -1.0697 0.0688 1.0000 Uiso R . . . . .
H661 H -1.0248 -1.2145 -1.2299 0.0709 1.0000 Uiso R . . . . .
H691 H -1.1460 -1.4398 -1.3491 0.0907 1.0000 Uiso R . . . . .
H701 H -1.2935 -1.6505 -1.3777 0.0771 1.0000 Uiso R . . . . .
H721 H -1.4769 -1.7148 -1.0183 0.0859 1.0000 Uiso R . . . . .
H731 H -1.5413 -1.8659 -1.1774 0.0818 1.0000 Uiso R . . . . .
H741 H -1.4413 -1.8196 -1.3063 0.0742 1.0000 Uiso R . . . . .
H19 H -0.7510 -0.5743 -0.9536 0.0561 1.0000 Uiso R . . . . .
H24 H -0.8209 -0.9661 -0.2838 0.0934 1.0000 Uiso R . . . . .
H25 H -0.7706 -0.6535 -1.0594 0.0563 1.0000 Uiso R . . . . .
H29 H -0.8021 -0.8840 -0.1768 0.0928 1.0000 Uiso R . . . . .
H36 H -0.5884 -1.0911 -0.8022 0.1092 1.0000 Uiso R . . . . .
H77 H -0.4529 -0.9704 -0.4421 0.1242 1.0000 Uiso R . . . . .
H1 H -0.7907 -0.4793 -0.7244 0.1640 1.0000 Uiso R . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C15 . O16 . H36 . 117.1 no
C13 . O17 . H77 . 81.6 no
C11 . O18 . C14 . 109.9(7) yes
C53 . O54 . H1 . 92.0 no
C49 . O56 . C52 . 117.2(7) yes
C2 . N1 . C6 . 116.4(6) yes
C2 . N3 . C4 . 111.5(7) yes
C4 . N7 . C8 . 105.4(6) yes
C4 . N7 . C11 . 126.4(6) yes
C8 . N7 . C11 . 127.3(6) yes
C5 . N9 . C8 . 103.8(6) yes
C6 . N10 . H19 . 120.5 no
C6 . N10 . H25 . 120.9 no
H19 . N10 . H25 . 118.6 no
C26 . N25 . C30 . 118.6(7) yes
C34 . N33 . C38 . 121.1(10) yes
C40 . N39 . C44 . 119.6(6) yes
C40 . N41 . C42 . 111.3(6) yes
C42 . N45 . C46 . 105.8(6) yes
C42 . N45 . C49 . 130.3(6) yes
C46 . N45 . C49 . 123.8(6) yes
C43 . N47 . C46 . 105.0(6) yes
C44 . N48 . H24 . 119.6 no
C44 . N48 . H29 . 120.2 no
H24 . N48 . H29 . 120.2 no
C64 . N63 . C68 . 118.7(7) yes
C72 . N71 . C76 . 116.0(8) yes
N1 . C2 . N3 . 130.4(7) yes
N1 . C2 . H21 . 114.8 no
N3 . C2 . H21 . 114.8 no
N7 . C4 . N3 . 128.2(7) yes
N7 . C4 . C5 . 106.1(6) yes
N3 . C4 . C5 . 125.7(7) yes
C4 . C5 . N9 . 111.3(7) yes
C4 . C5 . C6 . 116.0(6) yes
N9 . C5 . C6 . 132.6(6) yes
C5 . C6 . N10 . 121.0(7) yes
C5 . C6 . N1 . 120.0(6) yes
N10 . C6 . N1 . 118.9(6) yes
N7 . C8 . N9 . 113.3(6) yes
N7 . C8 . C19 . 124.4(6) yes
N9 . C8 . C19 . 122.3(6) yes
N7 . C11 . O18 . 108.0(7) yes
N7 . C11 . C12 . 114.6(6) yes
O18 . C11 . C12 . 107.7(6) yes
N7 . C11 . H111 . 109.0 no
O18 . C11 . H111 . 109.5 no
C12 . C11 . H111 . 108.0 no
C11 . C12 . C13 . 100.4(7) yes
C11 . C12 . H121 . 111.2 no
C13 . C12 . H121 . 111.7 no
C11 . C12 . H122 . 112.0 no
C13 . C12 . H122 . 112.5 no
H121 . C12 . H122 . 108.9 no
C12 . C13 . O17 . 108.2(6) yes
C12 . C13 . C14 . 104.6(7) yes
O17 . C13 . C14 . 111.6(8) yes
C12 . C13 . H131 . 110.7 no
O17 . C13 . H131 . 109.9 no
C14 . C13 . H131 . 111.7 no
C13 . C14 . O18 . 105.3(7) yes
C13 . C14 . C15 . 112.5(8) yes
O18 . C14 . C15 . 108.5(7) yes
C13 . C14 . H141 . 108.7 no
O18 . C14 . H141 . 111.0 no
C15 . C14 . H141 . 110.7 no
C14 . C15 . O16 . 110.9(7) yes
C14 . C15 . H151 . 109.2 no
O16 . C15 . H151 . 108.3 no
C14 . C15 . H152 . 108.9 no
O16 . C15 . H152 . 110.2 no
H151 . C15 . H152 . 109.3 no
C8 . C19 . C20 . 122.7(7) yes
C8 . C19 . C24 . 118.9(7) yes
C20 . C19 . C24 . 118.3(7) yes
C19 . C20 . C21 . 121.5(7) yes
C19 . C20 . H201 . 118.8 no
C21 . C20 . H201 . 119.7 no
C20 . C21 . C22 . 118.6(8) yes
C20 . C21 . H211 . 120.9 no
C22 . C21 . H211 . 120.5 no
C21 . C22 . C23 . 119.9(8) yes
C21 . C22 . C26 . 121.1(8) yes
C23 . C22 . C26 . 119.0(7) yes
C22 . C23 . C24 . 120.0(8) yes
C22 . C23 . H231 . 120.4 no
C24 . C23 . H231 . 119.6 no
C19 . C24 . C23 . 121.7(7) yes
C19 . C24 . H241 . 118.2 no
C23 . C24 . H241 . 120.1 no
C22 . C26 . N25 . 117.1(7) yes
C22 . C26 . C27 . 119.6(7) yes
N25 . C26 . C27 . 123.3(8) yes
C26 . C27 . C28 . 117.1(9) yes
C26 . C27 . H271 . 121.6 no
C28 . C27 . H271 . 121.3 no
C27 . C28 . C29 . 122.9(9) yes
C27 . C28 . H281 . 117.8 no
C29 . C28 . H281 . 119.3 no
C28 . C29 . C30 . 116.5(8) yes
C28 . C29 . C31 . 125.8(10) yes
C30 . C29 . C31 . 117.7(9) yes
C29 . C30 . N25 . 121.5(8) yes
C29 . C30 . C38 . 119.6(8) yes
N25 . C30 . C38 . 118.9(9) yes
C29 . C31 . C32 . 125.2(12) yes
C29 . C31 . H311 . 117.5 no
C32 . C31 . H311 . 117.2 no
C31 . C32 . C37 . 121.3(10) yes
C31 . C32 . H321 . 119.1 no
C37 . C32 . H321 . 119.7 no
N33 . C34 . C35 . 119.4(13) yes
N33 . C34 . H341 . 120.2 no
C35 . C34 . H341 . 120.4 no
C34 . C35 . C36 . 118.0(12) yes
C34 . C35 . H351 . 121.0 no
C36 . C35 . H351 . 121.0 no
C35 . C36 . C37 . 121.6(14) yes
C35 . C36 . H361 . 118.8 no
C37 . C36 . H361 . 119.6 no
C32 . C37 . C36 . 123.5(12) yes
C32 . C37 . C38 . 116.5(9) yes
C36 . C37 . C38 . 119.8(13) yes
C30 . C38 . C37 . 119.6(10) yes
C30 . C38 . N33 . 120.5(8) yes
C37 . C38 . N33 . 119.7(9) yes
N39 . C40 . N41 . 128.5(7) yes
N39 . C40 . H401 . 115.8 no
N41 . C40 . H401 . 115.7 no
N45 . C42 . N41 . 127.5(6) yes
N45 . C42 . C43 . 106.1(6) yes
N41 . C42 . C43 . 126.3(7) yes
N47 . C43 . C42 . 110.9(7) yes
N47 . C43 . C44 . 130.9(7) yes
C42 . C43 . C44 . 118.3(6) yes
C43 . C44 . N39 . 116.0(7) yes
C43 . C44 . N48 . 124.8(7) yes
N39 . C44 . N48 . 119.2(7) yes
N45 . C46 . N47 . 112.2(6) yes
N45 . C46 . C57 . 124.8(7) yes
N47 . C46 . C57 . 123.0(6) yes
N45 . C49 . O56 . 108.6(7) yes
N45 . C49 . C50 . 117.1(8) yes
O56 . C49 . C50 . 104.2(7) yes
N45 . C49 . H491 . 107.4 no
O56 . C49 . H491 . 110.4 no
C50 . C49 . H491 . 109.0 no
C49 . C50 . C51 . 104.3(8) yes
C49 . C50 . H501 . 111.6 no
C51 . C50 . H501 . 106.4 no
C49 . C50 . H502 . 111.8 no
C51 . C50 . H502 . 113.2 no
H501 . C50 . H502 . 109.4 no
C50 . C51 . O55 . 118.7(8) yes
C50 . C51 . C52 . 105.9(8) yes
O55 . C51 . C52 . 115.5(7) yes
C50 . C51 . H511 . 106.6 no
O55 . C51 . H511 . 104.7 no
C52 . C51 . H511 . 104.0 no
C51 . C52 . O56 . 102.5(7) yes
C51 . C52 . C53 . 118.2(8) yes
O56 . C52 . C53 . 111.2(9) yes
C51 . C52 . H521 . 108.4 no
O56 . C52 . H521 . 107.2 no
C53 . C52 . H521 . 108.8 no
C52 . C53 . O54 . 115.4(9) yes
C52 . C53 . H531 . 107.5 no
O54 . C53 . H531 . 107.5 no
C52 . C53 . H532 . 108.5 no
O54 . C53 . H532 . 108.6 no
H531 . C53 . H532 . 109.2 no
C46 . C57 . C58 . 122.9(6) yes
C46 . C57 . C62 . 118.6(7) yes
C58 . C57 . C62 . 118.5(7) yes
C57 . C58 . C59 . 120.2(7) yes
C57 . C58 . H581 . 120.7 no
C59 . C58 . H581 . 119.1 no
C58 . C59 . C60 . 122.2(7) yes
C58 . C59 . H591 . 118.0 no
C60 . C59 . H591 . 119.8 no
C59 . C60 . C61 . 117.3(7) yes
C59 . C60 . C64 . 122.9(7) yes
C61 . C60 . C64 . 119.8(6) yes
C60 . C61 . C62 . 120.0(7) yes
C60 . C61 . H611 . 120.4 no
C62 . C61 . H611 . 119.5 no
C57 . C62 . C61 . 121.8(8) yes
C57 . C62 . H621 . 118.1 no
C61 . C62 . H621 . 120.1 no
C60 . C64 . N63 . 115.2(7) yes
C60 . C64 . C65 . 122.8(7) yes
N63 . C64 . C65 . 122.0(7) yes
C64 . C65 . C66 . 120.2(8) yes
C64 . C65 . H651 . 120.5 no
C66 . C65 . H651 . 119.4 no
C65 . C66 . C67 . 117.8(8) yes
C65 . C66 . H661 . 120.8 no
C67 . C66 . H661 . 121.5 no
C66 . C67 . C68 . 119.1(7) yes
C66 . C67 . C69 . 119.8(8) yes
C68 . C67 . C69 . 121.0(8) yes
C67 . C68 . N63 . 122.1(7) yes
C67 . C68 . C76 . 118.6(7) yes
N63 . C68 . C76 . 119.3(7) yes
C67 . C69 . C70 . 119.6(9) yes
C67 . C69 . H691 . 119.6 no
C70 . C69 . H691 . 120.8 no
C69 . C70 . C75 . 119.9(8) yes
C69 . C70 . H701 . 119.6 no
C75 . C70 . H701 . 120.5 no
N71 . C72 . C73 . 124.4(11) yes
N71 . C72 . H721 . 117.6 no
C73 . C72 . H721 . 118.0 no
C72 . C73 . C74 . 120.2(9) yes
C72 . C73 . H731 . 119.4 no
C74 . C73 . H731 . 120.4 no
C73 . C74 . C75 . 119.8(9) yes
C73 . C74 . H741 . 120.3 no
C75 . C74 . H741 . 119.9 no
C70 . C75 . C74 . 122.3(9) yes
C70 . C75 . C76 . 120.5(9) yes
C74 . C75 . C76 . 117.1(10) yes
C75 . C76 . N71 . 122.4(8) yes
C75 . C76 . C68 . 120.3(8) yes
N71 . C76 . C68 . 117.3(7) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O16 . C15 . 1.464(11) yes
O16 . H36 . 0.820 no
O17 . C13 . 1.439(10) yes
O17 . H77 . 0.824 no
O18 . C11 . 1.414(10) yes
O18 . C14 . 1.429(10) yes
O54 . C53 . 1.413(12) yes
O54 . H1 . 0.836 no
O55 . C51 . 1.409(10) yes
O56 . C49 . 1.438(10) yes
O56 . C52 . 1.370(11) yes
N1 . C2 . 1.346(10) yes
N1 . C6 . 1.325(9) yes
N3 . C2 . 1.330(10) yes
N3 . C4 . 1.34(1) yes
N7 . C4 . 1.345(10) yes
N7 . C8 . 1.414(9) yes
N7 . C11 . 1.451(9) yes
N9 . C5 . 1.383(9) yes
N9 . C8 . 1.292(10) yes
N10 . C6 . 1.367(9) yes
N10 . H19 . 0.856 no
N10 . H25 . 0.859 no
N25 . C26 . 1.299(10) yes
N25 . C30 . 1.390(11) yes
N33 . C34 . 1.318(12) yes
N33 . C38 . 1.306(13) yes
N39 . C40 . 1.329(10) yes
N39 . C44 . 1.381(9) yes
N41 . C40 . 1.321(10) yes
N41 . C42 . 1.354(9) yes
N45 . C42 . 1.409(9) yes
N45 . C46 . 1.383(9) yes
N45 . C49 . 1.447(10) yes
N47 . C43 . 1.392(9) yes
N47 . C46 . 1.342(11) yes
N48 . C44 . 1.314(10) yes
N48 . H24 . 0.863 no
N48 . H29 . 0.872 no
N63 . C64 . 1.356(10) yes
N63 . C68 . 1.356(10) yes
N71 . C72 . 1.323(11) yes
N71 . C76 . 1.416(11) yes
C2 . H21 . 0.938 no
C4 . C5 . 1.387(11) yes
C5 . C6 . 1.429(10) yes
C8 . C19 . 1.486(11) yes
C11 . C12 . 1.503(12) yes
C11 . H111 . 0.983 no
C12 . C13 . 1.527(11) yes
C12 . H121 . 0.967 no
C12 . H122 . 0.969 no
C13 . C14 . 1.549(14) yes
C13 . H131 . 0.981 no
C14 . C15 . 1.531(13) yes
C14 . H141 . 0.979 no
C15 . H151 . 0.976 no
C15 . H152 . 0.970 no
C19 . C20 . 1.394(11) yes
C19 . C24 . 1.392(11) yes
C20 . C21 . 1.412(11) yes
C20 . H201 . 0.937 no
C21 . C22 . 1.383(11) yes
C21 . H211 . 0.932 no
C22 . C23 . 1.425(11) yes
C22 . C26 . 1.505(11) yes
C23 . C24 . 1.358(11) yes
C23 . H231 . 0.928 no
C24 . H241 . 0.925 no
C26 . C27 . 1.410(12) yes
C27 . C28 . 1.370(13) yes
C27 . H271 . 0.936 no
C28 . C29 . 1.360(14) yes
C28 . H281 . 0.923 no
C29 . C30 . 1.417(14) yes
C29 . C31 . 1.372(13) yes
C30 . C38 . 1.441(12) yes
C31 . C32 . 1.251(17) yes
C31 . H311 . 0.932 no
C32 . C37 . 1.494(18) yes
C32 . H321 . 0.943 no
C34 . C35 . 1.46(2) yes
C34 . H341 . 0.934 no
C35 . C36 . 1.27(2) yes
C35 . H351 . 0.929 no
C36 . C37 . 1.365(18) yes
C36 . H361 . 0.932 no
C37 . C38 . 1.380(14) yes
C40 . H401 . 0.934 no
C42 . C43 . 1.373(11) yes
C43 . C44 . 1.393(11) yes
C46 . C57 . 1.469(11) yes
C49 . C50 . 1.506(13) yes
C49 . H491 . 0.983 no
C50 . C51 . 1.524(13) yes
C50 . H501 . 0.974 no
C50 . H502 . 0.967 no
C51 . C52 . 1.537(13) yes
C51 . H511 . 0.997 no
C52 . C53 . 1.465(14) yes
C52 . H521 . 0.995 no
C53 . H531 . 0.977 no
C53 . H532 . 0.984 no
C57 . C58 . 1.362(10) yes
C57 . C62 . 1.395(10) yes
C58 . C59 . 1.376(10) yes
C58 . H581 . 0.933 no
C59 . C60 . 1.390(10) yes
C59 . H591 . 0.936 no
C60 . C61 . 1.397(10) yes
C60 . C64 . 1.477(10) yes
C61 . C62 . 1.366(11) yes
C61 . H611 . 0.934 no
C62 . H621 . 0.938 no
C64 . C65 . 1.391(10) yes
C65 . C66 . 1.393(11) yes
C65 . H651 . 0.941 no
C66 . C67 . 1.415(13) yes
C66 . H661 . 0.925 no
C67 . C68 . 1.399(11) yes
C67 . C69 . 1.472(13) yes
C68 . C76 . 1.409(12) yes
C69 . C70 . 1.371(14) yes
C69 . H691 . 0.933 no
C70 . C75 . 1.418(14) yes
C70 . H701 . 0.933 no
C72 . C73 . 1.417(14) yes
C72 . H721 . 0.922 no
C73 . C74 . 1.349(15) yes
C73 . H731 . 0.920 no
C74 . C75 . 1.418(14) yes
C74 . H741 . 0.922 no
C75 . C76 . 1.440(12) yes
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_site_symmetry_D
_geom_hbond_atom_site_label_H
_geom_hbond_site_symmetry_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
N48 . H29 . N1 1_556 176 0.87 2.17 3.043(10) yes
O16 . H36 . N3 . 165 0.82 1.99 2.794(9) yes
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.139 0.643 0.020 49.4 15.1
2 0.072 0.819 0.634 115.9 33.0
3 0.585 0.560 0.168 54.5 17.6
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653451
