#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/98/2209875.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_2209875
loop_
_publ_author_name
'Aghabozorg, Hossein'
'Ghadermazi, Mohammad'
'Attar Gharamaleki, Jafar'
_publ_section_title
;A proton-transfer compound:
 1,10-phenanthrolinium--2,4,5-tricarboxybenzoate--2,5-dicarboxybenzene-1,4-dicarboxylate
 (4/2/1)
;
_journal_coeditor_code           HK2066
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3174
_journal_page_last               o3176
_journal_paper_doi               10.1107/S1600536806024925
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          '4C12 H9 N2 + , 2C10 H5 O8 - , C10 H4 O8 2-'
_chemical_formula_moiety         '4C12 H9 N2 + , 2C10 H5 O8 - , C10 H4 O8 2-'
_chemical_formula_sum            'C78 H50 N8 O24'
_chemical_formula_weight         1483.26
_chemical_name_systematic
;
1,10-phenanthrolinium--2,4,5-tricarboxybenzoate--2,5-dicarboxybenzene-
1,4-dicarboxylate (2/1/0.5)
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   direct
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                107.075(5)
_cell_angle_beta                 101.375(5)
_cell_angle_gamma                104.174(5)
_cell_formula_units_Z            1
_cell_length_a                   8.6993(8)
_cell_length_b                   13.5070(14)
_cell_length_c                   15.1719(16)
_cell_measurement_reflns_used    999
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27
_cell_measurement_theta_min      3
_cell_volume                     1581.1(3)
_computing_cell_refinement       'SAINT-Plus (Bruker, 1998)'
_computing_data_collection       'SMART (Bruker, 1998)'
_computing_data_reduction        SAINT-Plus
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1998)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker SMART 1000 CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0298
_diffrn_reflns_av_sigmaI/netI    0.0549
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            16402
_diffrn_reflns_theta_full        28.00
_diffrn_reflns_theta_max         28.00
_diffrn_reflns_theta_min         2.52
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1998)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.558
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             766
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.293
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     496
_refine_ls_number_reflns         7598
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.070
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0493
_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)+(0.03P)²+0.6P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0994
_refine_ls_wR_factor_ref         0.1079
_reflns_number_gt                4972
_reflns_number_total             7598
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hk2066.cif
_cod_data_source_block           I
_cod_database_code               2209875
_cod_database_fobs_code          2209875
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 -0.15099(18) 0.10246(13) -0.29564(10) 0.0383(4) Uani d . 1
O O2 0.09565(16) 0.09845(11) -0.22839(9) 0.0281(3) Uani d . 1
O O3 0.25857(18) -0.01719(12) -0.27445(9) 0.0331(3) Uani d . 1
H H3O 0.2121 0.0423 -0.2434 0.040 Uiso d R 1
O O4 0.28069(17) -0.12797(11) -0.40680(9) 0.0276(3) Uani d . 1
N N1 0.05058(18) 0.19388(12) -0.05109(10) 0.0207(3) Uani d . 1
H H1N 0.0695 0.1548 -0.1110 0.025 Uiso d R 1
N N2 0.21161(18) 0.04581(12) -0.04508(11) 0.0229(3) Uani d . 1
C C1 -0.0296(2) 0.26451(15) -0.05983(14) 0.0239(4) Uani d . 1
H H1A -0.0573 0.2747 -0.1196 0.029 Uiso calc R 1
C C2 -0.0727(2) 0.32322(15) 0.01781(14) 0.0251(4) Uani d . 1
H H2A -0.1284 0.3743 0.0119 0.030 Uiso calc R 1
C C3 -0.0336(2) 0.30647(15) 0.10316(13) 0.0231(4) Uani d . 1
H H3A -0.0625 0.3465 0.1566 0.028 Uiso calc R 1
C C4 0.0486(2) 0.23092(14) 0.11275(13) 0.0208(4) Uani d . 1
C C5 0.0884(2) 0.20693(15) 0.19835(13) 0.0250(4) Uani d . 1
H H5A 0.0589 0.2433 0.2531 0.030 Uiso calc R 1
C C6 0.1673(2) 0.13335(15) 0.20264(13) 0.0244(4) Uani d . 1
H H6A 0.1916 0.1184 0.2603 0.029 Uiso calc R 1
C C7 0.2153(2) 0.07728(14) 0.12222(13) 0.0213(4) Uani d . 1
C C8 0.3000(2) 0.00095(15) 0.12388(14) 0.0253(4) Uani d . 1
H H8A 0.3319 -0.0139 0.1810 0.030 Uiso calc R 1
C C9 0.3359(2) -0.05158(15) 0.04229(14) 0.0271(4) Uani d . 1
H H9A 0.3919 -0.1038 0.0417 0.033 Uiso calc R 1
C C10 0.2883(2) -0.02668(15) -0.04057(14) 0.0255(4) Uani d . 1
H H10A 0.3127 -0.0643 -0.0969 0.031 Uiso calc R 1
C C11 0.1764(2) 0.09683(14) 0.03585(13) 0.0196(4) Uani d . 1
C C12 0.0917(2) 0.17514(14) 0.03232(12) 0.0193(4) Uani d . 1
C C13 -0.0244(2) 0.08096(15) -0.30277(13) 0.0238(4) Uani d . 1
C C14 0.2212(2) -0.05904(15) -0.36652(13) 0.0229(4) Uani d . 1
C C15 -0.0023(2) 0.03560(14) -0.40258(12) 0.0203(4) Uani d . 1
C C16 0.1036(2) -0.02368(14) -0.42955(13) 0.0200(4) Uani d . 1
C C17 0.1025(2) -0.05697(14) -0.52602(13) 0.0208(4) Uani d . 1
H H17A 0.1744 -0.0967 -0.5443 0.025 Uiso calc R 1
O O1' 0.53032(17) 0.24732(11) -0.06090(9) 0.0272(3) Uani d . 1
O O2' 0.37344(16) 0.34451(10) -0.09649(8) 0.0246(3) Uani d . 1
H H2'O 0.3194 0.4127 -0.0603 0.029 Uiso d R 1
O O3' 0.25511(15) 0.47862(10) -0.02270(8) 0.0233(3) Uani d . 1
O O4' 0.24143(16) 0.56247(10) 0.12264(9) 0.0257(3) Uani d . 1
O O5' 0.39276(17) 0.49155(12) 0.39640(9) 0.0329(3) Uani d . 1
O O6' 0.61320(16) 0.43736(11) 0.42788(9) 0.0282(3) Uani d . 1
H H6'O 0.6273 0.4667 0.4900 0.034 Uiso d R 1
O O7' 0.56500(15) 0.21816(10) 0.30675(9) 0.0258(3) Uani d . 1
H H7'O 0.6117 0.1890 0.3390 0.031 Uiso d R 1
O O8' 0.80675(17) 0.30206(12) 0.28891(10) 0.0345(4) Uani d . 1
N N1' 0.38113(18) 0.26601(12) -0.27893(10) 0.0210(3) Uani d . 1
H H1'N 0.3652 0.2936 -0.2148 0.025 Uiso d R 1
N N2' 0.1385(2) 0.36040(13) -0.26673(11) 0.0266(4) Uani d . 1
C C1' 0.5006(2) 0.22064(15) -0.27945(14) 0.0254(4) Uani d . 1
H H1'A 0.5547 0.2125 -0.2224 0.031 Uiso calc R 1
C C2' 0.5470(2) 0.18507(17) -0.36293(14) 0.0297(5) Uani d . 1
H H2'A 0.6316 0.1519 -0.3636 0.036 Uiso calc R 1
C C3' 0.4687(2) 0.19861(16) -0.44442(14) 0.0293(4) Uani d . 1
H H3'A 0.5005 0.1755 -0.5015 0.035 Uiso calc R 1
C C4' 0.3427(2) 0.24589(15) -0.44430(13) 0.0231(4) Uani d . 1
C C5' 0.2555(3) 0.26249(16) -0.52678(14) 0.0290(4) Uani d . 1
H H5'A 0.2851 0.2420 -0.5849 0.035 Uiso calc R 1
C C6' 0.1329(3) 0.30642(16) -0.52331(14) 0.0299(5) Uani d . 1
H H6'A 0.0759 0.3149 -0.5794 0.036 Uiso calc R 1
C C7' 0.0863(2) 0.34098(15) -0.43606(13) 0.0247(4) Uani d . 1
C C8' -0.0394(2) 0.38789(16) -0.42853(15) 0.0321(5) Uani d . 1
H H8'A -0.1010 0.3971 -0.4830 0.039 Uiso calc R 1
C C9' -0.0732(3) 0.42042(18) -0.34209(16) 0.0347(5) Uani d . 1
H H9'A -0.1574 0.4531 -0.3356 0.042 Uiso calc R 1
C C10' 0.0191(3) 0.40468(17) -0.26306(15) 0.0314(5) Uani d . 1
H H10B -0.0059 0.4272 -0.2036 0.038 Uiso calc R 1
C C11' 0.1710(2) 0.32907(14) -0.35272(13) 0.0214(4) Uani d . 1
C C12' 0.2992(2) 0.27991(14) -0.35871(12) 0.0204(4) Uani d . 1
C C13' 0.4569(2) 0.31287(14) -0.03664(12) 0.0193(4) Uani d . 1
C C14' 0.2893(2) 0.49746(14) 0.06957(12) 0.0192(4) Uani d . 1
C C15' 0.4631(2) 0.35888(14) 0.06966(12) 0.0176(4) Uani d . 1
C C16' 0.3898(2) 0.43517(14) 0.11272(12) 0.0181(4) Uani d . 1
C C17' 0.4065(2) 0.46091(14) 0.21110(12) 0.0188(4) Uani d . 1
H H17B 0.3576 0.5121 0.2411 0.023 Uiso calc R 1
C C18' 0.4910(2) 0.41536(14) 0.26686(12) 0.0190(4) Uani d . 1
C C19' 0.5665(2) 0.34145(14) 0.22473(12) 0.0193(4) Uani d . 1
C C20' 0.5510(2) 0.31545(14) 0.12732(12) 0.0199(4) Uani d . 1
H H20A 0.6026 0.2656 0.0983 0.024 Uiso calc R 1
C C21' 0.4972(2) 0.45047(14) 0.37017(13) 0.0208(4) Uani d . 1
C C22' 0.6605(2) 0.28631(15) 0.27840(12) 0.0220(4) Uani d . 1
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_site_symmetry_1
_geom_angle
_geom_angle_publ_flag
C13 O2 H3O . 117.3 ?
C14 O3 H3O . 119.5 ?
C1 N1 C12 . 122.25(16) yes
C1 N1 H1N . 113.2 ?
C12 N1 H1N . 124.5 ?
C10 N2 C11 . 116.52(16) yes
N1 C1 C2 . 120.43(17) yes
N1 C1 H1A . 119.8 ?
C2 C1 H1A . 119.8 ?
C3 C2 C1 . 119.08(17) ?
C3 C2 H2A . 120.5 ?
C1 C2 H2A . 120.5 ?
C2 C3 C4 . 120.97(17) ?
C2 C3 H3A . 119.5 ?
C4 C3 H3A . 119.5 ?
C3 C4 C12 . 117.51(16) ?
C3 C4 C5 . 123.95(17) ?
C12 C4 C5 . 118.54(16) ?
C6 C5 C4 . 120.90(17) ?
C6 C5 H5A . 119.5 ?
C4 C5 H5A . 119.5 ?
C5 C6 C7 . 121.45(17) ?
C5 C6 H6A . 119.3 ?
C7 C6 H6A . 119.3 ?
C11 C7 C8 . 116.82(17) ?
C11 C7 C6 . 119.76(16) ?
C8 C7 C6 . 123.42(17) ?
C9 C8 C7 . 119.33(18) ?
C9 C8 H8A . 120.3 ?
C7 C8 H8A . 120.3 ?
C8 C9 C10 . 118.76(17) ?
C8 C9 H9A . 120.6 ?
C10 C9 H9A . 120.6 ?
N2 C10 C9 . 124.12(18) yes
N2 C10 H10A . 117.9 ?
C9 C10 H10A . 117.9 ?
N2 C11 C7 . 124.41(16) yes
N2 C11 C12 . 117.49(16) yes
C7 C11 C12 . 118.10(16) yes
N1 C12 C4 . 119.75(16) yes
N1 C12 C11 . 119.01(16) yes
C4 C12 C11 . 121.24(16) yes
O1 C13 O2 . 122.52(17) yes
O1 C13 C15 . 119.41(16) yes
O2 C13 C15 . 118.03(16) yes
O4 C14 O3 . 121.48(16) yes
O4 C14 C16 . 118.01(16) yes
O3 C14 C16 . 120.50(16) yes
C17 C15 C16 2_554 117.95(16) ?
C17 C15 C13 2_554 113.96(16) ?
C16 C15 C13 . 128.09(16) ?
C17 C16 C15 . 117.82(16) ?
C17 C16 C14 . 114.08(16) ?
C15 C16 C14 . 128.10(16) ?
C15 C17 C16 2_554 124.22(17) ?
C15 C17 H17A 2_554 117.9 ?
C16 C17 H17A . 117.9 ?
C13' O2' H2'O . 114.2 ?
C14' O3' H2'O . 109.8 ?
C21' O6' H6'O . 117.7 ?
C22' O7' H7'O . 116.1 ?
C1' N1' C12' . 122.33(16) yes
C1' N1' H1'N . 113.4 ?
C12' N1' H1'N . 124.1 ?
C10' N2' C11' . 116.59(16) yes
N1' C1' C2' . 120.46(17) yes
N1' C1' H1'A . 119.8 ?
C2' C1' H1'A . 119.8 ?
C3' C2' C1' . 118.96(18) ?
C3' C2' H2'A . 120.5 ?
C1' C2' H2'A . 120.5 ?
C2' C3' C4' . 120.77(18) ?
C2' C3' H3'A . 119.6 ?
C4' C3' H3'A . 119.6 ?
C3' C4' C12' . 118.34(17) ?
C3' C4' C5' . 123.77(17) ?
C12' C4' C5' . 117.89(17) ?
C6' C5' C4' . 121.35(18) ?
C6' C5' H5'A . 119.3 ?
C4' C5' H5'A . 119.3 ?
C5' C6' C7' . 121.24(18) ?
C5' C6' H6'A . 119.4 ?
C7' C6' H6'A . 119.4 ?
C8' C7' C11' . 117.03(18) ?
C8' C7' C6' . 123.44(17) ?
C11' C7' C6' . 119.53(17) ?
C9' C8' C7' . 119.49(18) ?
C9' C8' H8'A . 120.3 ?
C7' C8' H8'A . 120.3 ?
C8' C9' C10' . 118.87(19) ?
C8' C9' H9'A . 120.6 ?
C10' C9' H9'A . 120.6 ?
N2' C10' C9' . 123.85(19) yes
N2' C10' H10B . 118.1 ?
C9' C10' H10B . 118.1 ?
N2' C11' C7' . 124.18(17) yes
N2' C11' C12' . 117.61(16) yes
C7' C11' C12' . 118.21(16) yes
N1' C12' C4' . 119.13(17) yes
N1' C12' C11' . 119.12(16) yes
C4' C12' C11' . 121.75(16) yes
O1' C13' O2' . 123.03(16) yes
O1' C13' C15' . 118.84(15) yes
O2' C13' C15' . 118.13(15) yes
O4' C14' O3' . 121.63(16) yes
O4' C14' C16' . 118.86(15) yes
O3' C14' C16' . 119.50(15) yes
C20' C15' C16' . 118.70(16) ?
C20' C15' C13' . 113.24(15) ?
C16' C15' C13' . 128.04(15) ?
C17' C16' C15' . 117.46(15) ?
C17' C16' C14' . 111.69(15) ?
C15' C16' C14' . 130.85(15) ?
C18' C17' C16' . 123.14(17) ?
C18' C17' H17B . 118.4 ?
C16' C17' H17B . 118.4 ?
C17' C18' C19' . 119.46(16) ?
C17' C18' C21' . 116.78(16) ?
C19' C18' C21' . 123.76(15) ?
C20' C19' C18' . 117.91(16) ?
C20' C19' C22' . 118.13(16) ?
C18' C19' C22' . 123.94(15) ?
C19' C20' C15' . 123.31(17) ?
C19' C20' H20A . 118.3 ?
C15' C20' H20A . 118.3 ?
O5' C21' O6' . 123.74(16) yes
O5' C21' C18' . 119.22(15) yes
O6' C21' C18' . 117.03(16) yes
O8' C22' O7' . 125.52(17) yes
O8' C22' C19' . 121.63(17) yes
O7' C22' C19' . 112.78(15) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C13 . 1.222(2) yes
O2 C13 . 1.295(2) yes
O3 C14 . 1.282(2) yes
O3 H3O . 1.0210 ?
O4 C14 . 1.239(2) yes
N1 C1 . 1.333(2) ?
N1 C12 . 1.359(2) ?
N1 H1N . 0.9756 ?
N2 C10 . 1.322(2) ?
N2 C11 . 1.353(2) ?
C1 C2 . 1.389(3) ?
C1 H1A . 0.9500 ?
C2 C3 . 1.371(3) ?
C2 H2A . 0.9500 ?
C3 C4 . 1.406(2) ?
C3 H3A . 0.9500 ?
C4 C12 . 1.406(3) ?
C4 C5 . 1.427(2) ?
C5 C6 . 1.348(3) ?
C5 H5A . 0.9500 ?
C6 C7 . 1.431(3) ?
C6 H6A . 0.9500 ?
C7 C11 . 1.405(2) ?
C7 C8 . 1.410(3) ?
C8 C9 . 1.371(3) ?
C8 H8A . 0.9500 ?
C9 C10 . 1.406(3) ?
C9 H9A . 0.9500 ?
C10 H10A . 0.9500 ?
C11 C12 . 1.437(2) ?
C13 C15 . 1.528(3) ?
C14 C16 . 1.520(2) ?
C15 C17 2_554 1.397(2) ?
C15 C16 . 1.406(2) ?
C16 C17 . 1.396(2) ?
C17 C15 2_554 1.397(2) ?
C17 H17A . 0.9500 ?
O1' C13' . 1.227(2) yes
O2' C13' . 1.286(2) yes
O2' H2'O . 1.1788 ?
O3' C14' . 1.305(2) yes
O3' H2'O . 1.2249 ?
O4' C14' . 1.220(2) yes
O5' C21' . 1.245(2) yes
O6' C21' . 1.283(2) yes
O6' H6'O . 0.8781 ?
O7' C22' . 1.312(2) yes
O7' H7'O . 0.8200 ?
O8' C22' . 1.207(2) yes
N1' C1' . 1.330(2) ?
N1' C12' . 1.366(2) ?
N1' H1'N . 0.9854 ?
N2' C10' . 1.322(2) ?
N2' C11' . 1.357(2) ?
C1' C2' . 1.392(3) ?
C1' H1'A . 0.9500 ?
C2' C3' . 1.374(3) ?
C2' H2'A . 0.9500 ?
C3' C4' . 1.397(3) ?
C3' H3'A . 0.9500 ?
C4' C12' . 1.404(2) ?
C4' C5' . 1.437(3) ?
C5' C6' . 1.344(3) ?
C5' H5'A . 0.9500 ?
C6' C7' . 1.441(3) ?
C6' H6'A . 0.9500 ?
C7' C8' . 1.399(3) ?
C7' C11' . 1.406(2) ?
C8' C9' . 1.370(3) ?
C8' H8'A . 0.9500 ?
C9' C10' . 1.408(3) ?
C9' H9'A . 0.9500 ?
C10' H10B . 0.9500 ?
C11' C12' . 1.435(2) ?
C13' C15' . 1.533(2) ?
C14' C16' . 1.535(2) ?
C15' C20' . 1.397(2) ?
C15' C16' . 1.409(2) ?
C16' C17' . 1.398(2) ?
C17' C18' . 1.384(2) ?
C17' H17B . 0.9500 ?
C18' C19' . 1.396(2) ?
C18' C21' . 1.484(2) ?
C19' C20' . 1.385(2) ?
C19' C22' . 1.510(2) ?
C20' H20A . 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2' H2'O O3' 1_555 1.18 1.23 2.402(2) 176 yes
N1 H1N O2 1_555 0.98 1.80 2.771(2) 171 yes
O6' H6'O O5' 2_666 0.88 1.71 2.570(2) 167 yes
O7' H7'O O4 2_655 0.82 1.76 2.583(2) 178 yes
O2 H3O O3 1_555 1.42 1.02 2.402(2) 159 yes
N1' H1'N O2' 1_555 0.99 1.70 2.678(2) 170 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C12 N1 C1 C2 . . 0.8(3) ?
N1 C1 C2 C3 . . -0.9(3) ?
C1 C2 C3 C4 . . -0.2(3) ?
C2 C3 C4 C12 . . 1.2(3) ?
C2 C3 C4 C5 . . -177.98(17) ?
C3 C4 C5 C6 . . 179.90(18) ?
C12 C4 C5 C6 . . 0.7(3) ?
C4 C5 C6 C7 . . 0.5(3) ?
C5 C6 C7 C11 . . -1.5(3) ?
C5 C6 C7 C8 . . 179.05(18) ?
C11 C7 C8 C9 . . -1.7(3) ?
C6 C7 C8 C9 . . 177.78(17) ?
C7 C8 C9 C10 . . 0.6(3) ?
C11 N2 C10 C9 . . -0.9(3) ?
C8 C9 C10 N2 . . 0.7(3) ?
C10 N2 C11 C7 . . -0.3(3) ?
C10 N2 C11 C12 . . -179.40(16) ?
C8 C7 C11 N2 . . 1.5(3) ?
C6 C7 C11 N2 . . -177.92(16) ?
C8 C7 C11 C12 . . -179.32(16) ?
C6 C7 C11 C12 . . 1.2(2) ?
C1 N1 C12 C4 . . 0.3(3) ?
C1 N1 C12 C11 . . 179.29(16) ?
C3 C4 C12 N1 . . -1.3(2) ?
C5 C4 C12 N1 . . 177.93(16) ?
C3 C4 C12 C11 . . 179.77(16) ?
C5 C4 C12 C11 . . -1.0(3) ?
N2 C11 C12 N1 . . 0.3(2) ?
C7 C11 C12 N1 . . -178.91(15) ?
N2 C11 C12 C4 . . 179.22(16) ?
C7 C11 C12 C4 . . 0.0(2) ?
O1 C13 C15 C17 . 2_554 20.5(3) ?
O2 C13 C15 C17 . 2_554 -157.26(17) ?
O1 C13 C15 C16 . . -159.18(19) yes
O2 C13 C15 C16 . . 23.0(3) yes
C17 C15 C16 C17 2_554 . 0.3(3) ?
C13 C15 C16 C17 . . 179.97(17) ?
C17 C15 C16 C14 2_554 . -178.73(17) ?
C13 C15 C16 C14 . . 1.0(3) ?
O4 C14 C16 C17 . . -12.5(2) yes
O3 C14 C16 C17 . . 166.62(17) yes
O4 C14 C16 C15 . . 166.58(18) ?
O3 C14 C16 C15 . . -14.3(3) ?
C15 C16 C17 C15 . 2_554 -0.3(3) ?
C14 C16 C17 C15 . 2_554 178.85(17) ?
C12' N1' C1' C2' . . 0.0(3) ?
N1' C1' C2' C3' . . 0.7(3) ?
C1' C2' C3' C4' . . -0.9(3) ?
C2' C3' C4' C12' . . 0.5(3) ?
C2' C3' C4' C5' . . -179.96(19) ?
C3' C4' C5' C6' . . 178.65(19) ?
C12' C4' C5' C6' . . -1.8(3) ?
C4' C5' C6' C7' . . 1.4(3) ?
C5' C6' C7' C8' . . 179.50(19) ?
C5' C6' C7' C11' . . 0.3(3) ?
C11' C7' C8' C9' . . 0.6(3) ?
C6' C7' C8' C9' . . -178.67(19) ?
C7' C8' C9' C10' . . -0.6(3) ?
C11' N2' C10' C9' . . -0.1(3) ?
C8' C9' C10' N2' . . 0.4(3) ?
C10' N2' C11' C7' . . 0.0(3) ?
C10' N2' C11' C12' . . -179.48(17) ?
C8' C7' C11' N2' . . -0.3(3) ?
C6' C7' C11' N2' . . 178.99(17) ?
C8' C7' C11' C12' . . 179.22(17) ?
C6' C7' C11' C12' . . -1.5(3) ?
C1' N1' C12' C4' . . -0.4(3) ?
C1' N1' C12' C11' . . 179.69(17) ?
C3' C4' C12' N1' . . 0.2(3) ?
C5' C4' C12' N1' . . -179.42(16) ?
C3' C4' C12' C11' . . -179.92(17) ?
C5' C4' C12' C11' . . 0.5(3) ?
N2' C11' C12' N1' . . 0.6(2) ?
C7' C11' C12' N1' . . -178.97(16) ?
N2' C11' C12' C4' . . -179.35(17) ?
C7' C11' C12' C4' . . 1.1(3) ?
O1' C13' C15' C20' . . -2.1(2) yes
O2' C13' C15' C20' . . 177.39(15) yes
O1' C13' C15' C16' . . 179.26(17) ?
O2' C13' C15' C16' . . -1.2(3) ?
C20' C15' C16' C17' . . -1.5(2) ?
C13' C15' C16' C17' . . 177.05(16) ?
C20' C15' C16' C14' . . 179.06(17) ?
C13' C15' C16' C14' . . -2.4(3) ?
O4' C14' C16' C17' . . 2.4(2) yes
O3' C14' C16' C17' . . -176.58(15) yes
O4' C14' C16' C15' . . -178.11(17) ?
O3' C14' C16' C15' . . 2.9(3) ?
C15' C16' C17' C18' . . 0.1(3) ?
C14' C16' C17' C18' . . 179.68(16) ?
C16' C17' C18' C19' . . 1.2(3) ?
C16' C17' C18' C21' . . -179.67(16) ?
C17' C18' C19' C20' . . -1.0(3) ?
C21' C18' C19' C20' . . 179.88(16) ?
C17' C18' C19' C22' . . -179.53(16) ?
C21' C18' C19' C22' . . 1.4(3) ?
C18' C19' C20' C15' . . -0.4(3) ?
C22' C19' C20' C15' . . 178.22(16) ?
C16' C15' C20' C19' . . 1.7(3) ?
C13' C15' C20' C19' . . -177.07(16) ?
C17' C18' C21' O5' . . 20.3(3) yes
C19' C18' C21' O5' . . -160.61(18) ?
C17' C18' C21' O6' . . -158.96(16) yes
C19' C18' C21' O6' . . 20.2(3) ?
C20' C19' C22' O8' . . 65.0(2) yes
C18' C19' C22' O8' . . -116.5(2) ?
C20' C19' C22' O7' . . -112.10(18) yes
C18' C19' C22' O7' . . 66.4(2) ?
