#------------------------------------------------------------------------------
#$Date: 2020-09-04 03:36:14 +0300 (Fri, 04 Sep 2020) $
#$Revision: 255874 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/88/1558856.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_1558856
loop_
_publ_author_name
'Atilaw, Yoseph'
'Muiva-Mutisya, Lois'
'Bogaerts, Jonathan'
'Duffy, Sandra'
'Valkonen, Arto'
'Heydenreich, Matthias'
'Avery, Vicky M.'
'Rissanen, Kari'
'Erdélyi, Máté'
'Yenesew, Abiy'
_publ_section_title
;
 Prenylated Flavonoids from the Roots of Tephrosia rhodesica.
;
_journal_issue                   8
_journal_name_full               'Journal of natural products'
_journal_page_first              2390
_journal_page_last               2398
_journal_paper_doi               10.1021/acs.jnatprod.0c00245
_journal_volume                  83
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C42 H44 O7'
_chemical_formula_sum            'C42 H44 O7'
_chemical_formula_weight         660.77
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 111.677(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.9977(3)
_cell_length_b                   9.6100(2)
_cell_length_c                   15.9499(4)
_cell_measurement_reflns_used    6316
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      73.9840
_cell_measurement_theta_min      3.6400
_cell_volume                     1851.38(8)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_molecular_graphics    SHELXL-2018/3
_computing_publication_material  SHELXL-2018/3
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SIR2014 (Burla, et al., 2014)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 5.1977
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11327
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.949
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.278
_diffrn_reflns_theta_min         3.659
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.641
_exptl_absorpt_correction_T_max  0.910
_exptl_absorpt_correction_T_min  0.811
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.185
_exptl_crystal_description       needle
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.150
_exptl_crystal_size_mid          0.030
_exptl_crystal_size_min          0.020
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details
;
 Flack x determined using 2813 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.15(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     452
_refine_ls_number_reflns         7155
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0353
_refine_ls_shift/su_max          0.035
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0472P)²+0.1406P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0866
_refine_ls_wR_factor_ref         0.0888
_reflns_Friedel_coverage         0.839
_reflns_Friedel_fraction_full    0.977
_reflns_Friedel_fraction_max     0.924
_reflns_number_gt                6629
_reflns_number_total             7155
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            np0c00245_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments          'Adding full bibliography for 1558856.cif.'
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               1558856
_shelx_shelxl_version_number     2018/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.910
_shelx_estimated_absorpt_t_max   0.987
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.20148(12) 0.62698(17) 0.30586(10) 0.0278(3) Uani 1 1 d . . . . .
O5 O 0.29768(13) 0.28103(17) 0.53582(11) 0.0311(3) Uani 1 1 d . . . . .
O7 O -0.08254(14) 0.4219(2) 0.37334(12) 0.0375(4) Uani 1 1 d . . . . .
O1P O 0.68174(12) 0.71446(17) 0.75673(10) 0.0262(3) Uani 1 1 d . . . . .
O4P O 0.79965(13) 0.46876(19) 0.60206(11) 0.0316(3) Uani 1 1 d . . . . .
O5P O 0.59918(12) 0.42142(16) 0.49580(11) 0.0262(3) Uani 1 1 d D . . . .
O7P O 0.31454(12) 0.65558(17) 0.56162(11) 0.0274(3) Uani 1 1 d D . . . .
C2 C 0.31720(17) 0.6589(2) 0.32871(15) 0.0249(4) Uani 1 1 d . . . . .
H2 H 0.342123 0.722909 0.381913 0.030 Uiso 1 1 calc R U . . .
C3 C 0.38487(18) 0.5268(2) 0.35271(15) 0.0250(4) Uani 1 1 d . . . . .
H3A H 0.463231 0.548279 0.363486 0.030 Uiso 1 1 calc R U . . .
H3B H 0.357549 0.460489 0.301747 0.030 Uiso 1 1 calc R U . . .
C4 C 0.37678(17) 0.4600(2) 0.43785(14) 0.0243(4) Uani 1 1 d . . . . .
H4 H 0.403530 0.361971 0.440078 0.029 Uiso 1 1 calc R U . . .
C4A C 0.25503(18) 0.4520(2) 0.42401(14) 0.0244(4) Uani 1 1 d . . . . .
C5 C 0.21647(19) 0.3569(2) 0.47322(15) 0.0264(4) Uani 1 1 d . . . . .
C6 C 0.1047(2) 0.3441(2) 0.45827(16) 0.0289(5) Uani 1 1 d . . . . .
H6 H 0.080429 0.280504 0.492687 0.035 Uiso 1 1 calc R U . . .
C7 C 0.02853(18) 0.4262(2) 0.39167(15) 0.0282(5) Uani 1 1 d . . . . .
C8 C 0.06123(18) 0.5193(2) 0.33900(15) 0.0275(4) Uani 1 1 d . . . . .
C8A C 0.17490(18) 0.5317(2) 0.35785(14) 0.0248(4) Uani 1 1 d . . . . .
C9 C 0.2632(2) 0.1751(3) 0.58277(18) 0.0367(5) Uani 1 1 d . . . . .
H9A H 0.328510 0.128265 0.625546 0.055 Uiso 1 1 calc R U . . .
H9B H 0.220575 0.217308 0.615595 0.055 Uiso 1 1 calc R U . . .
H9C H 0.216976 0.107111 0.539336 0.055 Uiso 1 1 calc R U . . .
C10 C -0.1220(2) 0.3299(3) 0.4246(2) 0.0420(6) Uani 1 1 d . . . . .
H10A H -0.202722 0.337613 0.404344 0.063 Uiso 1 1 calc R U . . .
H10B H -0.101863 0.234122 0.416118 0.063 Uiso 1 1 calc R U . . .
H10C H -0.088593 0.354644 0.488618 0.063 Uiso 1 1 calc R U . . .
C1M C 0.32783(19) 0.7328(2) 0.24868(15) 0.0280(4) Uani 1 1 d . . . . .
C2M C 0.2472(2) 0.7257(3) 0.16314(17) 0.0381(5) Uani 1 1 d . . . . .
H2M H 0.180958 0.675108 0.153328 0.046 Uiso 1 1 calc R U . . .
C3M C 0.2629(3) 0.7924(3) 0.09116(19) 0.0472(7) Uani 1 1 d . . . . .
H3M H 0.207047 0.787459 0.032521 0.057 Uiso 1 1 calc R U . . .
C4M C 0.3589(3) 0.8657(3) 0.1045(2) 0.0462(7) Uani 1 1 d . . . . .
H4M H 0.369219 0.910723 0.055129 0.055 Uiso 1 1 calc R U . . .
C5M C 0.4398(2) 0.8733(3) 0.1896(2) 0.0410(6) Uani 1 1 d . . . . .
H5M H 0.505929 0.923948 0.198992 0.049 Uiso 1 1 calc R U . . .
C6M C 0.4249(2) 0.8071(2) 0.26170(17) 0.0321(5) Uani 1 1 d . . . . .
H6M H 0.481106 0.812281 0.320190 0.039 Uiso 1 1 calc R U . . .
C1N C -0.02128(19) 0.6049(3) 0.26527(16) 0.0323(5) Uani 1 1 d . . . . .
H1NA H 0.001782 0.608033 0.212675 0.039 Uiso 1 1 calc R U . . .
H1NB H -0.094605 0.559080 0.245831 0.039 Uiso 1 1 calc R U . . .
C2N C -0.03168(19) 0.7516(3) 0.29482(16) 0.0322(5) Uani 1 1 d . . . . .
H2N H 0.034389 0.793576 0.334820 0.039 Uiso 1 1 calc R U . . .
C3N C -0.1230(2) 0.8288(3) 0.27118(18) 0.0383(6) Uani 1 1 d . . . . .
C4N C -0.2356(2) 0.7819(4) 0.2077(2) 0.0505(7) Uani 1 1 d . . . . .
H4NA H -0.253931 0.829191 0.149534 0.076 Uiso 1 1 calc R U . . .
H4NB H -0.291147 0.804900 0.233508 0.076 Uiso 1 1 calc R U . . .
H4NC H -0.234749 0.681046 0.198770 0.076 Uiso 1 1 calc R U . . .
C5N C -0.1179(3) 0.9747(3) 0.3068(2) 0.0515(7) Uani 1 1 d . . . . .
H5N1 H -0.167048 0.982633 0.340575 0.077 Uiso 1 1 calc R U . . .
H5N2 H -0.141427 1.040416 0.256208 0.077 Uiso 1 1 calc R U . . .
H5N3 H -0.041758 0.996040 0.346669 0.077 Uiso 1 1 calc R U . . .
C2P C 0.78811(17) 0.6453(2) 0.79790(15) 0.0273(4) Uani 1 1 d . . . . .
H2P H 0.775671 0.552518 0.820972 0.033 Uiso 1 1 calc R U . . .
C3P C 0.84062(18) 0.6224(3) 0.72817(15) 0.0297(5) Uani 1 1 d . . . . .
H3PA H 0.858853 0.713458 0.708101 0.036 Uiso 1 1 calc R U . . .
H3PB H 0.910264 0.569203 0.755662 0.036 Uiso 1 1 calc R U . . .
C4P C 0.76296(18) 0.5441(2) 0.64832(15) 0.0270(5) Uani 1 1 d . . . . .
C4AP C 0.64619(18) 0.5651(2) 0.62684(15) 0.0234(4) Uani 1 1 d . . . . .
C5P C 0.56631(17) 0.5060(2) 0.54892(14) 0.0227(4) Uani 1 1 d . . . . .
C6P C 0.45322(17) 0.5312(2) 0.52358(15) 0.0225(4) Uani 1 1 d . . . . .
C7P C 0.42250(17) 0.6208(2) 0.58002(14) 0.0228(4) Uani 1 1 d . . . . .
C8P C 0.49750(17) 0.6827(2) 0.65822(14) 0.0232(4) Uani 1 1 d . . . . .
C8AP C 0.60840(17) 0.6525(2) 0.68122(14) 0.0234(4) Uani 1 1 d . . . . .
C1Q C 0.85315(18) 0.7351(2) 0.87730(15) 0.0298(5) Uani 1 1 d . . . . .
C2Q C 0.8433(2) 0.7126(3) 0.95982(18) 0.0394(6) Uani 1 1 d . . . . .
H2Q H 0.798264 0.638533 0.966097 0.047 Uiso 1 1 calc R U . . .
C3Q C 0.8986(3) 0.7971(3) 1.03364(19) 0.0485(7) Uani 1 1 d . . . . .
H3Q H 0.892114 0.779591 1.090106 0.058 Uiso 1 1 calc R U . . .
C4Q C 0.9626(2) 0.9057(3) 1.02487(19) 0.0478(7) Uani 1 1 d . . . . .
H4Q H 0.999708 0.964320 1.074902 0.057 Uiso 1 1 calc R U . . .
C5Q C 0.9725(3) 0.9289(4) 0.9433(2) 0.0621(10) Uani 1 1 d . . . . .
H5Q H 1.016603 1.003993 0.937015 0.075 Uiso 1 1 calc R U . . .
C6Q C 0.9186(3) 0.8438(4) 0.87004(19) 0.0539(8) Uani 1 1 d . . . . .
H6Q H 0.926820 0.860583 0.814155 0.065 Uiso 1 1 calc R U . . .
H5P H 0.671(2) 0.419(5) 0.518(3) 0.081 Uiso 1 1 d D U . . .
H7P H 0.272(3) 0.607(4) 0.518(2) 0.081 Uiso 1 1 d D U . . .
C1R C 0.45818(18) 0.7812(2) 0.71448(15) 0.0261(4) Uani 1 1 d . . . . .
H1RA H 0.521548 0.838422 0.752516 0.031 Uiso 1 1 calc R U . . .
H1RB H 0.402029 0.844808 0.673608 0.031 Uiso 1 1 calc R U . . .
C2R C 0.4091(2) 0.7082(3) 0.77412(17) 0.0337(5) Uani 1 1 d . . . . .
H2R H 0.346025 0.651778 0.744618 0.040 Uiso 1 1 calc R U . . .
C3R C 0.4439(3) 0.7136(3) 0.8633(2) 0.0493(7) Uani 1 1 d . . . . .
C4R C 0.3860(4) 0.6342(5) 0.9138(3) 0.0777(13) Uani 1 1 d . . . . .
H4RA H 0.319144 0.590644 0.870869 0.117 Uiso 1 1 calc R U . . .
H4RB H 0.365515 0.698003 0.953016 0.117 Uiso 1 1 calc R U . . .
H4RC H 0.435548 0.562106 0.950640 0.117 Uiso 1 1 calc R U . . .
C5R C 0.5429(4) 0.7941(7) 0.9219(3) 0.1008(19) Uani 1 1 d . . . . .
H5RA H 0.588141 0.819858 0.887001 0.151 Uiso 1 1 calc R U . . .
H5RB H 0.586820 0.736599 0.973492 0.151 Uiso 1 1 calc R U . . .
H5RC H 0.518508 0.878471 0.943755 0.151 Uiso 1 1 calc R U . . .
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'
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
C8A O1 C2 117.64(17) . . ?
C5 O5 C9 117.13(18) . . ?
C7 O7 C10 118.3(2) . . ?
C8AP O1P C2P 115.86(17) . . ?
C5P O5P H5P 108(3) . . ?
C7P O7P H7P 111(3) . . ?
O1 C2 C1M 107.37(18) . . ?
O1 C2 C3 109.87(17) . . ?
C1M C2 C3 112.50(17) . . ?
O1 C2 H2 109.0 . . ?
C1M C2 H2 109.0 . . ?
C3 C2 H2 109.0 . . ?
C2 C3 C4 110.54(17) . . ?
C2 C3 H3A 109.5 . . ?
C4 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
C4 C3 H3B 109.5 . . ?
H3A C3 H3B 108.1 . . ?
C4A C4 C6P 116.91(18) . . ?
C4A C4 C3 107.45(18) . . ?
C6P C4 C3 111.69(18) . . ?
C4A C4 H4 106.7 . . ?
C6P C4 H4 106.7 . . ?
C3 C4 H4 106.7 . . ?
C8A C4A C5 116.98(19) . . ?
C8A C4A C4 121.75(19) . . ?
C5 C4A C4 121.14(19) . . ?
O5 C5 C6 123.7(2) . . ?
O5 C5 C4A 114.52(19) . . ?
C6 C5 C4A 121.7(2) . . ?
C5 C6 C7 118.9(2) . . ?
C5 C6 H6 120.6 . . ?
C7 C6 H6 120.6 . . ?
O7 C7 C8 115.1(2) . . ?
O7 C7 C6 122.8(2) . . ?
C8 C7 C6 122.1(2) . . ?
C7 C8 C8A 117.2(2) . . ?
C7 C8 C1N 122.1(2) . . ?
C8A C8 C1N 120.7(2) . . ?
O1 C8A C8 114.27(19) . . ?
O1 C8A C4A 122.62(19) . . ?
C8 C8A C4A 123.1(2) . . ?
O5 C9 H9A 109.5 . . ?
O5 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
O5 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O7 C10 H10A 109.5 . . ?
O7 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O7 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C2M C1M C6M 119.1(2) . . ?
C2M C1M C2 122.6(2) . . ?
C6M C1M C2 118.3(2) . . ?
C1M C2M C3M 120.1(3) . . ?
C1M C2M H2M 119.9 . . ?
C3M C2M H2M 119.9 . . ?
C4M C3M C2M 120.5(3) . . ?
C4M C3M H3M 119.8 . . ?
C2M C3M H3M 119.8 . . ?
C3M C4M C5M 119.8(2) . . ?
C3M C4M H4M 120.1 . . ?
C5M C4M H4M 120.1 . . ?
C4M C5M C6M 120.1(3) . . ?
C4M C5M H5M 119.9 . . ?
C6M C5M H5M 119.9 . . ?
C5M C6M C1M 120.4(2) . . ?
C5M C6M H6M 119.8 . . ?
C1M C6M H6M 119.8 . . ?
C2N C1N C8 112.7(2) . . ?
C2N C1N H1NA 109.1 . . ?
C8 C1N H1NA 109.1 . . ?
C2N C1N H1NB 109.1 . . ?
C8 C1N H1NB 109.1 . . ?
H1NA C1N H1NB 107.8 . . ?
C3N C2N C1N 127.3(2) . . ?
C3N C2N H2N 116.3 . . ?
C1N C2N H2N 116.3 . . ?
C2N C3N C5N 120.2(3) . . ?
C2N C3N C4N 124.5(3) . . ?
C5N C3N C4N 115.4(2) . . ?
C3N C4N H4NA 109.5 . . ?
C3N C4N H4NB 109.5 . . ?
H4NA C4N H4NB 109.5 . . ?
C3N C4N H4NC 109.5 . . ?
H4NA C4N H4NC 109.5 . . ?
H4NB C4N H4NC 109.5 . . ?
C3N C5N H5N1 109.5 . . ?
C3N C5N H5N2 109.5 . . ?
H5N1 C5N H5N2 109.5 . . ?
C3N C5N H5N3 109.5 . . ?
H5N1 C5N H5N3 109.5 . . ?
H5N2 C5N H5N3 109.5 . . ?
O1P C2P C1Q 105.20(18) . . ?
O1P C2P C3P 110.16(17) . . ?
C1Q C2P C3P 115.68(19) . . ?
O1P C2P H2P 108.5 . . ?
C1Q C2P H2P 108.5 . . ?
C3P C2P H2P 108.5 . . ?
C4P C3P C2P 110.48(18) . . ?
C4P C3P H3PA 109.6 . . ?
C2P C3P H3PA 109.6 . . ?
C4P C3P H3PB 109.6 . . ?
C2P C3P H3PB 109.6 . . ?
H3PA C3P H3PB 108.1 . . ?
O4P C4P C4AP 122.7(2) . . ?
O4P C4P C3P 120.55(19) . . ?
C4AP C4P C3P 116.7(2) . . ?
C5P C4AP C8AP 117.93(19) . . ?
C5P C4AP C4P 121.36(19) . . ?
C8AP C4AP C4P 120.6(2) . . ?
O5P C5P C6P 117.78(19) . . ?
O5P C5P C4AP 119.59(18) . . ?
C6P C5P C4AP 122.63(19) . . ?
C5P C6P C7P 116.05(19) . . ?
C5P C6P C4 116.77(18) . . ?
C7P C6P C4 127.18(19) . . ?
O7P C7P C8P 114.20(18) . . ?
O7P C7P C6P 121.66(19) . . ?
C8P C7P C6P 124.15(19) . . ?
C8AP C8P C7P 117.54(19) . . ?
C8AP C8P C1R 121.39(19) . . ?
C7P C8P C1R 121.06(18) . . ?
O1P C8AP C8P 117.56(19) . . ?
O1P C8AP C4AP 120.70(18) . . ?
C8P C8AP C4AP 121.7(2) . . ?
C6Q C1Q C2Q 118.3(2) . . ?
C6Q C1Q C2P 122.3(2) . . ?
C2Q C1Q C2P 119.3(2) . . ?
C1Q C2Q C3Q 120.8(3) . . ?
C1Q C2Q H2Q 119.6 . . ?
C3Q C2Q H2Q 119.6 . . ?
C4Q C3Q C2Q 120.0(3) . . ?
C4Q C3Q H3Q 120.0 . . ?
C2Q C3Q H3Q 120.0 . . ?
C5Q C4Q C3Q 119.5(3) . . ?
C5Q C4Q H4Q 120.3 . . ?
C3Q C4Q H4Q 120.3 . . ?
C4Q C5Q C6Q 120.6(3) . . ?
C4Q C5Q H5Q 119.7 . . ?
C6Q C5Q H5Q 119.7 . . ?
C1Q C6Q C5Q 120.8(3) . . ?
C1Q C6Q H6Q 119.6 . . ?
C5Q C6Q H6Q 119.6 . . ?
C2R C1R C8P 113.47(19) . . ?
C2R C1R H1RA 108.9 . . ?
C8P C1R H1RA 108.9 . . ?
C2R C1R H1RB 108.9 . . ?
C8P C1R H1RB 108.9 . . ?
H1RA C1R H1RB 107.7 . . ?
C3R C2R C1R 127.3(2) . . ?
C3R C2R H2R 116.4 . . ?
C1R C2R H2R 116.4 . . ?
C2R C3R C5R 124.4(3) . . ?
C2R C3R C4R 121.2(3) . . ?
C5R C3R C4R 114.4(3) . . ?
C3R C4R H4RA 109.5 . . ?
C3R C4R H4RB 109.5 . . ?
H4RA C4R H4RB 109.5 . . ?
C3R C4R H4RC 109.5 . . ?
H4RA C4R H4RC 109.5 . . ?
H4RB C4R H4RC 109.5 . . ?
C3R C5R H5RA 109.5 . . ?
C3R C5R H5RB 109.5 . . ?
H5RA C5R H5RB 109.5 . . ?
C3R C5R H5RC 109.5 . . ?
H5RA C5R H5RC 109.5 . . ?
H5RB C5R H5RC 109.5 . . ?
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
O1 C8A 1.363(3) . ?
O1 C2 1.444(2) . ?
O5 C5 1.365(3) . ?
O5 C9 1.430(3) . ?
O7 C7 1.364(3) . ?
O7 C10 1.422(3) . ?
O1P C8AP 1.366(3) . ?
O1P C2P 1.454(3) . ?
O4P C4P 1.247(3) . ?
O5P C5P 1.352(3) . ?
O5P H5P 0.87(2) . ?
O7P C7P 1.365(2) . ?
O7P H7P 0.85(2) . ?
C2 C1M 1.511(3) . ?
C2 C3 1.511(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.541(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C4A 1.517(3) . ?
C4 C6P 1.524(3) . ?
C4 H4 1.0000 . ?
C4A C8A 1.404(3) . ?
C4A C5 1.412(3) . ?
C5 C6 1.387(3) . ?
C6 C7 1.399(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.397(3) . ?
C8 C8A 1.400(3) . ?
C8 C1N 1.509(3) . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C1M C2M 1.381(4) . ?
C1M C6M 1.397(3) . ?
C2M C3M 1.395(4) . ?
C2M H2M 0.9500 . ?
C3M C4M 1.379(5) . ?
C3M H3M 0.9500 . ?
C4M C5M 1.379(5) . ?
C4M H4M 0.9500 . ?
C5M C6M 1.389(3) . ?
C5M H5M 0.9500 . ?
C6M H6M 0.9500 . ?
C1N C2N 1.508(4) . ?
C1N H1NA 0.9900 . ?
C1N H1NB 0.9900 . ?
C2N C3N 1.330(4) . ?
C2N H2N 0.9500 . ?
C3N C5N 1.504(5) . ?
C3N C4N 1.509(4) . ?
C4N H4NA 0.9800 . ?
C4N H4NB 0.9800 . ?
C4N H4NC 0.9800 . ?
C5N H5N1 0.9800 . ?
C5N H5N2 0.9800 . ?
C5N H5N3 0.9800 . ?
C2P C1Q 1.507(3) . ?
C2P C3P 1.520(3) . ?
C2P H2P 1.0000 . ?
C3P C4P 1.503(3) . ?
C3P H3PA 0.9900 . ?
C3P H3PB 0.9900 . ?
C4P C4AP 1.441(3) . ?
C4AP C5P 1.411(3) . ?
C4AP C8AP 1.419(3) . ?
C5P C6P 1.394(3) . ?
C6P C7P 1.406(3) . ?
C7P C8P 1.400(3) . ?
C8P C8AP 1.381(3) . ?
C8P C1R 1.517(3) . ?
C1Q C6Q 1.379(4) . ?
C1Q C2Q 1.386(4) . ?
C2Q C3Q 1.392(4) . ?
C2Q H2Q 0.9500 . ?
C3Q C4Q 1.374(5) . ?
C3Q H3Q 0.9500 . ?
C4Q C5Q 1.372(5) . ?
C4Q H4Q 0.9500 . ?
C5Q C6Q 1.386(4) . ?
C5Q H5Q 0.9500 . ?
C6Q H6Q 0.9500 . ?
C1R C2R 1.501(3) . ?
C1R H1RA 0.9900 . ?
C1R H1RB 0.9900 . ?
C2R C3R 1.325(4) . ?
C2R H2R 0.9500 . ?
C3R C5R 1.497(5) . ?
C3R C4R 1.498(4) . ?
C4R H4RA 0.9800 . ?
C4R H4RB 0.9800 . ?
C4R H4RC 0.9800 . ?
C5R H5RA 0.9800 . ?
C5R H5RB 0.9800 . ?
C5R H5RC 0.9800 . ?
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
_geom_hbond_publ_flag
O5P H5P O4P 0.87(2) 1.78(3) 2.570(2) 150(4) . 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8A O1 C2 C1M 164.37(18) . . . . ?
C8A O1 C2 C3 41.7(2) . . . . ?
O1 C2 C3 C4 -63.8(2) . . . . ?
C1M C2 C3 C4 176.68(18) . . . . ?
C2 C3 C4 C4A 49.7(2) . . . . ?
C2 C3 C4 C6P -79.8(2) . . . . ?
C6P C4 C4A C8A 109.1(2) . . . . ?
C3 C4 C4A C8A -17.3(3) . . . . ?
C6P C4 C4A C5 -75.2(3) . . . . ?
C3 C4 C4A C5 158.33(19) . . . . ?
C9 O5 C5 C6 5.2(3) . . . . ?
C9 O5 C5 C4A -175.12(19) . . . . ?
C8A C4A C5 O5 179.22(18) . . . . ?
C4 C4A C5 O5 3.4(3) . . . . ?
C8A C4A C5 C6 -1.1(3) . . . . ?
C4 C4A C5 C6 -177.0(2) . . . . ?
O5 C5 C6 C7 -179.4(2) . . . . ?
C4A C5 C6 C7 1.0(3) . . . . ?
C10 O7 C7 C8 -179.7(2) . . . . ?
C10 O7 C7 C6 0.2(3) . . . . ?
C5 C6 C7 O7 -179.0(2) . . . . ?
C5 C6 C7 C8 0.9(3) . . . . ?
O7 C7 C8 C8A 177.4(2) . . . . ?
C6 C7 C8 C8A -2.5(3) . . . . ?
O7 C7 C8 C1N -1.9(3) . . . . ?
C6 C7 C8 C1N 178.1(2) . . . . ?
C2 O1 C8A C8 172.21(18) . . . . ?
C2 O1 C8A C4A -8.4(3) . . . . ?
C7 C8 C8A O1 -178.23(19) . . . . ?
C1N C8 C8A O1 1.2(3) . . . . ?
C7 C8 C8A C4A 2.3(3) . . . . ?
C1N C8 C8A C4A -178.3(2) . . . . ?
C5 C4A C8A O1 -179.99(19) . . . . ?
C4 C4A C8A O1 -4.2(3) . . . . ?
C5 C4A C8A C8 -0.6(3) . . . . ?
C4 C4A C8A C8 175.2(2) . . . . ?
O1 C2 C1M C2M -19.1(3) . . . . ?
C3 C2 C1M C2M 101.9(3) . . . . ?
O1 C2 C1M C6M 163.19(19) . . . . ?
C3 C2 C1M C6M -75.8(3) . . . . ?
C6M C1M C2M C3M -0.3(4) . . . . ?
C2 C1M C2M C3M -178.0(2) . . . . ?
C1M C2M C3M C4M 0.3(5) . . . . ?
C2M C3M C4M C5M -0.2(5) . . . . ?
C3M C4M C5M C6M 0.2(4) . . . . ?
C4M C5M C6M C1M -0.3(4) . . . . ?
C2M C1M C6M C5M 0.3(4) . . . . ?
C2 C1M C6M C5M 178.1(2) . . . . ?
C7 C8 C1N C2N 99.1(3) . . . . ?
C8A C8 C1N C2N -80.3(3) . . . . ?
C8 C1N C2N C3N -144.0(2) . . . . ?
C1N C2N C3N C5N -179.4(2) . . . . ?
C1N C2N C3N C4N -0.7(4) . . . . ?
C8AP O1P C2P C1Q 178.81(17) . . . . ?
C8AP O1P C2P C3P 53.5(2) . . . . ?
O1P C2P C3P C4P -55.1(2) . . . . ?
C1Q C2P C3P C4P -174.20(18) . . . . ?
C2P C3P C4P O4P -151.9(2) . . . . ?
C2P C3P C4P C4AP 30.4(3) . . . . ?
O4P C4P C4AP C5P -3.1(3) . . . . ?
C3P C4P C4AP C5P 174.58(19) . . . . ?
O4P C4P C4AP C8AP -179.6(2) . . . . ?
C3P C4P C4AP C8AP -2.0(3) . . . . ?
C8AP C4AP C5P O5P -179.55(19) . . . . ?
C4P C4AP C5P O5P 3.8(3) . . . . ?
C8AP C4AP C5P C6P 0.5(3) . . . . ?
C4P C4AP C5P C6P -176.1(2) . . . . ?
O5P C5P C6P C7P -179.32(18) . . . . ?
C4AP C5P C6P C7P 0.6(3) . . . . ?
O5P C5P C6P C4 0.2(3) . . . . ?
C4AP C5P C6P C4 -179.90(19) . . . . ?
C4A C4 C6P C5P 162.95(18) . . . . ?
C3 C4 C6P C5P -72.7(2) . . . . ?
C4A C4 C6P C7P -17.6(3) . . . . ?
C3 C4 C6P C7P 106.7(2) . . . . ?
C5P C6P C7P O7P 178.84(19) . . . . ?
C4 C6P C7P O7P -0.6(3) . . . . ?
C5P C6P C7P C8P -0.7(3) . . . . ?
C4 C6P C7P C8P 179.9(2) . . . . ?
O7P C7P C8P C8AP -179.96(18) . . . . ?
C6P C7P C8P C8AP -0.4(3) . . . . ?
O7P C7P C8P C1R -1.0(3) . . . . ?
C6P C7P C8P C1R 178.5(2) . . . . ?
C2P O1P C8AP C8P 158.00(19) . . . . ?
C2P O1P C8AP C4AP -24.6(3) . . . . ?
C7P C8P C8AP O1P 179.00(18) . . . . ?
C1R C8P C8AP O1P 0.1(3) . . . . ?
C7P C8P C8AP C4AP 1.7(3) . . . . ?
C1R C8P C8AP C4AP -177.28(19) . . . . ?
C5P C4AP C8AP O1P -178.99(18) . . . . ?
C4P C4AP C8AP O1P -2.3(3) . . . . ?
C5P C4AP C8AP C8P -1.7(3) . . . . ?
C4P C4AP C8AP C8P 175.0(2) . . . . ?
O1P C2P C1Q C6Q -89.2(3) . . . . ?
C3P C2P C1Q C6Q 32.6(3) . . . . ?
O1P C2P C1Q C2Q 87.7(3) . . . . ?
C3P C2P C1Q C2Q -150.5(2) . . . . ?
C6Q C1Q C2Q C3Q -0.4(4) . . . . ?
C2P C1Q C2Q C3Q -177.4(3) . . . . ?
C1Q C2Q C3Q C4Q 1.0(5) . . . . ?
C2Q C3Q C4Q C5Q -0.8(5) . . . . ?
C3Q C4Q C5Q C6Q 0.0(6) . . . . ?
C2Q C1Q C6Q C5Q -0.4(5) . . . . ?
C2P C1Q C6Q C5Q 176.5(3) . . . . ?
C4Q C5Q C6Q C1Q 0.7(6) . . . . ?
C8AP C8P C1R C2R -102.7(2) . . . . ?
C7P C8P C1R C2R 78.4(3) . . . . ?
C8P C1R C2R C3R 119.8(3) . . . . ?
C1R C2R C3R C5R -1.3(6) . . . . ?
C1R C2R C3R C4R -179.9(3) . . . . ?
