 
data_donw098 
  
_audit_creation_method            'SHELXL-2018/3' 
_shelx_SHELXL_version_number      '2018/3' 
_chemical_name_systematic         ? 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety 
 'C20 H28 B O5 P' 
_chemical_formula_sum 
 'C20 H28 B O5 P' 
_chemical_formula_weight          390.20 
  
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' 
 'B'  'B'   0.0090   0.0039 
 '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' 
 'P'  'P'   0.2955   0.4335 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
  
_space_group_crystal_system       monoclinic 
_space_group_IT_number            14 
_space_group_name_H-M_alt         'P 21/n' 
_space_group_name_Hall            '-P 2yn' 
  
_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. 
; 
  
loop_ 
 _space_group_symop_operation_xyz 
 'x, y, z' 
 '-x+1/2, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x-1/2, -y-1/2, z-1/2' 
  
_cell_length_a                    13.531(3) 
_cell_length_b                    16.1027(19) 
_cell_length_c                    19.882(3) 
_cell_angle_alpha                 90 
_cell_angle_beta                  105.235(9) 
_cell_angle_gamma                 90 
_cell_volume                      4179.7(11) 
_cell_formula_units_Z             8 
_cell_measurement_temperature     100(2) 
_cell_measurement_reflns_used     9653 
_cell_measurement_theta_min       5.37 
_cell_measurement_theta_max       74.96 
  
_exptl_crystal_description        block 
_exptl_crystal_colour             colourless 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     ? 
_exptl_crystal_density_diffrn     1.240 
_exptl_crystal_F_000              1664 
_exptl_transmission_factor_min    ? 
_exptl_transmission_factor_max    ? 
_exptl_crystal_size_max           0.400 
_exptl_crystal_size_mid           0.201 
_exptl_crystal_size_min           0.126 
_exptl_absorpt_coefficient_mu     1.389 
_shelx_estimated_absorpt_T_min    0.606 
_shelx_estimated_absorpt_T_max    0.844 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.6022 
_exptl_absorpt_correction_T_max   0.7539 
_exptl_absorpt_process_details 
; 
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D., 
 J. Appl. Cryst. 48 (2015) 3-10 
; 
_exptl_absorpt_special_details    ? 
_diffrn_ambient_temperature       100(2) 
_diffrn_radiation_wavelength      1.54178 
_diffrn_radiation_type            CuK\a 
_diffrn_source                    ? 
_diffrn_measurement_device_type   'Bruker AXS APEX diffractometer' 
_diffrn_measurement_method        'φ and ω scans' 
_diffrn_detector_area_resol_mean  8.33 
_diffrn_reflns_number             85458 
_diffrn_reflns_av_unetI/netI      0.0290 
_diffrn_reflns_av_R_equivalents   0.0517 
_diffrn_reflns_limit_h_min        -16 
_diffrn_reflns_limit_h_max        16 
_diffrn_reflns_limit_k_min        -20 
_diffrn_reflns_limit_k_max        19 
_diffrn_reflns_limit_l_min        -24 
_diffrn_reflns_limit_l_max        24 
_diffrn_reflns_theta_min          3.559 
_diffrn_reflns_theta_max          75.338 
_diffrn_reflns_theta_full         67.679 
_diffrn_measured_fraction_theta_max   0.995 
_diffrn_measured_fraction_theta_full  1.000 
_diffrn_reflns_Laue_measured_fraction_max    0.995 
_diffrn_reflns_Laue_measured_fraction_full   1.000 
_diffrn_reflns_point_group_measured_fraction_max   0.995 
_diffrn_reflns_point_group_measured_fraction_full  1.000 
_reflns_number_total              8607 
_reflns_number_gt                 7379 
_reflns_threshold_expression      'I > 2σ(I)' 
_reflns_Friedel_coverage          0.000 
_reflns_Friedel_fraction_max      . 
_reflns_Friedel_fraction_full     . 
  
_reflns_special_details 
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
; 
  
_computing_data_collection        'Bruker APEX2' 
_computing_cell_refinement        'Bruker SAINT' 
_computing_data_reduction         'Bruker SAINT' 
_computing_structure_solution     'SHELXS-97 (Sheldrick 2008)' 
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' 
_computing_molecular_graphics     'Bruker SHELXTL' 
_computing_publication_material   'Bruker SHELXTL' 
_refine_special_details           ? 
_refine_ls_structure_factor_coef  Fsqd 
_refine_ls_matrix_type            full 
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
'w=1/[σ²(Fo²)+(0.0496P)²+1.8080P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      iterative 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     constr 
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        . 
_refine_ls_number_reflns          8607 
_refine_ls_number_parameters      499 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0469 
_refine_ls_R_factor_gt            0.0390 
_refine_ls_wR_factor_ref          0.1073 
_refine_ls_wR_factor_gt           0.0999 
_refine_ls_goodness_of_fit_ref    1.044 
_refine_ls_restrained_S_all       1.044 
_refine_ls_shift/su_max           0.001 
_refine_ls_shift/su_mean          0.000 
  
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 
P1 P 0.36437(3) 0.57710(2) 0.70627(2) 0.02947(10) Uani 1 1 d . . . . . 
O1 O 0.46749(9) 0.56850(8) 0.69566(6) 0.0397(3) Uani 1 1 d . . . . . 
C1 C 0.36455(11) 0.52595(8) 0.78641(7) 0.0262(3) Uani 1 1 d . . . . . 
C2 C 0.45881(11) 0.49335(9) 0.82151(8) 0.0283(3) Uani 1 1 d . . . . . 
O2 O 0.27458(9) 0.54423(7) 0.64539(6) 0.0374(3) Uani 1 1 d . . . . . 
C3 C 0.46831(12) 0.45406(9) 0.88689(8) 0.0323(3) Uani 1 1 d . . . . . 
H3 H 0.532237 0.430724 0.911112 0.039 Uiso 1 1 calc R U . . . 
O3 O 0.32422(9) 0.66842(7) 0.70788(6) 0.0398(3) Uani 1 1 d . . . . . 
C4 C 0.38702(12) 0.44926(10) 0.91555(8) 0.0334(3) Uani 1 1 d . . . . . 
H4 H 0.395565 0.422903 0.959454 0.040 Uiso 1 1 calc R U . . . 
O4 O 0.62963(8) 0.56194(7) 0.81810(6) 0.0357(2) Uani 1 1 d . . . . . 
C5 C 0.29028(11) 0.48288(9) 0.88092(8) 0.0296(3) Uani 1 1 d . . . . . 
O5 O 0.59701(8) 0.43328(6) 0.76719(6) 0.0319(2) Uani 1 1 d . . . . . 
C6 C 0.20641(13) 0.47992(10) 0.91159(9) 0.0347(3) Uani 1 1 d . . . . . 
H6 H 0.214712 0.453931 0.955627 0.042 Uiso 1 1 calc R U . . . 
C7 C 0.11405(12) 0.51409(10) 0.87831(9) 0.0366(3) Uani 1 1 d . . . . . 
H7 H 0.058772 0.512363 0.899469 0.044 Uiso 1 1 calc R U . . . 
C8 C 0.10084(12) 0.55185(10) 0.81269(9) 0.0357(3) Uani 1 1 d . . . . . 
H8 H 0.036301 0.575191 0.789756 0.043 Uiso 1 1 calc R U . . . 
C9 C 0.17986(11) 0.55543(9) 0.78135(8) 0.0313(3) Uani 1 1 d . . . . . 
H9 H 0.169274 0.580777 0.736871 0.038 Uiso 1 1 calc R U . . . 
C10 C 0.27722(11) 0.52160(9) 0.81481(8) 0.0275(3) Uani 1 1 d . . . . . 
C11 C 0.28440(14) 0.46192(11) 0.61665(9) 0.0406(4) Uani 1 1 d . . . . . 
H11A H 0.351734 0.437421 0.640114 0.049 Uiso 1 1 calc R U . . . 
H11B H 0.279252 0.466187 0.566170 0.049 Uiso 1 1 calc R U . . . 
C12 C 0.20017(18) 0.40865(14) 0.62827(12) 0.0595(5) Uani 1 1 d . . . . . 
H12A H 0.133891 0.432782 0.604022 0.089 Uiso 1 1 calc R U . . . 
H12B H 0.205413 0.405406 0.678308 0.089 Uiso 1 1 calc R U . . . 
H12C H 0.205880 0.352781 0.610111 0.089 Uiso 1 1 calc R U . . . 
C13 C 0.39061(17) 0.73162(11) 0.74837(9) 0.0473(4) Uani 1 1 d . . . . . 
H13A H 0.462609 0.712340 0.760698 0.057 Uiso 1 1 calc R U . . . 
H13B H 0.370800 0.742751 0.792045 0.057 Uiso 1 1 calc R U . . . 
C14 C 0.38007(16) 0.80918(11) 0.70537(10) 0.0456(4) Uani 1 1 d . . . . . 
H14A H 0.402660 0.798230 0.663245 0.068 Uiso 1 1 calc R U . . . 
H14B H 0.422434 0.853182 0.732580 0.068 Uiso 1 1 calc R U . . . 
H14C H 0.308234 0.826822 0.692163 0.068 Uiso 1 1 calc R U . . . 
C15 C 0.72761(12) 0.53227(10) 0.81052(8) 0.0336(3) Uani 1 1 d . . . . . 
C16 C 0.69627(12) 0.45838(10) 0.75764(8) 0.0321(3) Uani 1 1 d . . . . . 
C17 C 0.78123(14) 0.60378(12) 0.78523(10) 0.0443(4) Uani 1 1 d . . . . . 
H17A H 0.845796 0.584163 0.777284 0.066 Uiso 1 1 calc R U . . . 
H17B H 0.795412 0.647821 0.820487 0.066 Uiso 1 1 calc R U . . . 
H17C H 0.737174 0.625597 0.741569 0.066 Uiso 1 1 calc R U . . . 
C18 C 0.78869(15) 0.50527(14) 0.88319(9) 0.0505(5) Uani 1 1 d . . . . . 
H18A H 0.752696 0.459855 0.899514 0.076 Uiso 1 1 calc R U . . . 
H18B H 0.795826 0.552340 0.915361 0.076 Uiso 1 1 calc R U . . . 
H18C H 0.856735 0.486293 0.881333 0.076 Uiso 1 1 calc R U . . . 
C19 C 0.67828(13) 0.48481(11) 0.68165(8) 0.0354(3) Uani 1 1 d . . . . . 
H19A H 0.654679 0.436954 0.651215 0.053 Uiso 1 1 calc R U . . . 
H19B H 0.742401 0.505822 0.673961 0.053 Uiso 1 1 calc R U . . . 
H19C H 0.626213 0.528613 0.670995 0.053 Uiso 1 1 calc R U . . . 
C20 C 0.76702(15) 0.38354(12) 0.77354(10) 0.0452(4) Uani 1 1 d . . . . . 
H20A H 0.742602 0.340727 0.738024 0.068 Uiso 1 1 calc R U . . . 
H20B H 0.767516 0.361301 0.819510 0.068 Uiso 1 1 calc R U . . . 
H20C H 0.836552 0.400332 0.773336 0.068 Uiso 1 1 calc R U . . . 
B1 B 0.55884(13) 0.50011(11) 0.79471(9) 0.0321(3) Uani 1 1 d . . . . . 
P1_1 P 0.08256(3) 0.35549(2) 0.39399(2) 0.03038(10) Uani 1 1 d . . . . . 
O1_1 O 0.18840(9) 0.35928(7) 0.38803(6) 0.0396(3) Uani 1 1 d . . . . . 
O2_1 O -0.00081(9) 0.32966(7) 0.32552(6) 0.0343(2) Uani 1 1 d . . . . . 
O3_1 O 0.03513(9) 0.44052(7) 0.40939(7) 0.0410(3) Uani 1 1 d . . . . . 
O4_1 O 0.32162(8) 0.20952(6) 0.44921(5) 0.0292(2) Uani 1 1 d . . . . . 
O5_1 O 0.33752(8) 0.32211(7) 0.52147(6) 0.0357(2) Uani 1 1 d . . . . . 
C1_1 C 0.07359(11) 0.28471(9) 0.46158(7) 0.0268(3) Uani 1 1 d . . . . . 
C2_1 C 0.16482(11) 0.24589(9) 0.49549(7) 0.0269(3) Uani 1 1 d . . . . . 
C3_1 C 0.16399(11) 0.18814(9) 0.54961(8) 0.0299(3) Uani 1 1 d . . . . . 
H3_1 H 0.225269 0.159671 0.572084 0.036 Uiso 1 1 calc R U . . . 
C4_1 C 0.07667(12) 0.17297(9) 0.56977(7) 0.0299(3) Uani 1 1 d . . . . . 
H4_1 H 0.078510 0.134567 0.606352 0.036 Uiso 1 1 calc R U . . . 
C5_1 C -0.01661(11) 0.21341(9) 0.53718(7) 0.0277(3) Uani 1 1 d . . . . . 
C6_1 C -0.10675(12) 0.19830(10) 0.55910(8) 0.0325(3) Uani 1 1 d . . . . . 
H6_1 H -0.104214 0.162313 0.597377 0.039 Uiso 1 1 calc R U . . . 
C7_1 C -0.19712(12) 0.23523(11) 0.52542(9) 0.0366(3) Uani 1 1 d . . . . . 
H7_1 H -0.257170 0.224634 0.540272 0.044 Uiso 1 1 calc R U . . . 
C8_1 C -0.20162(12) 0.28908(11) 0.46863(9) 0.0374(3) Uani 1 1 d . . . . . 
H8_1 H -0.264958 0.314009 0.445220 0.045 Uiso 1 1 calc R U . . . 
C9_1 C -0.11559(12) 0.30575(10) 0.44696(8) 0.0323(3) Uani 1 1 d . . . . . 
H9_1 H -0.119993 0.342394 0.408841 0.039 Uiso 1 1 calc R U . . . 
C10_1 C -0.01984(11) 0.26906(9) 0.48062(7) 0.0273(3) Uani 1 1 d . . . . . 
C11_1 C 0.01083(14) 0.24989(11) 0.29349(9) 0.0394(4) Uani 1 1 d . . . . . 
H11A_1 H 0.045940 0.209814 0.329671 0.047 Uiso 1 1 calc R U . . . 
H11B_1 H 0.052538 0.256807 0.259745 0.047 Uiso 1 1 calc R U . . . 
C12_1 C -0.09325(15) 0.21843(12) 0.25707(11) 0.0480(4) Uani 1 1 d . . . . . 
H12A_1 H -0.127660 0.258706 0.221677 0.072 Uiso 1 1 calc R U . . . 
H12B_1 H -0.133503 0.210699 0.291006 0.072 Uiso 1 1 calc R U . . . 
H12C_1 H -0.086920 0.165234 0.234627 0.072 Uiso 1 1 calc R U . . . 
C13_1 C 0.09651(18) 0.51469(12) 0.42866(11) 0.0527(5) Uani 1 1 d . . . . . 
H13A_1 H 0.169966 0.499476 0.442805 0.063 Uiso 1 1 calc R U . . . 
H13B_1 H 0.079296 0.541582 0.468906 0.063 Uiso 1 1 calc R U . . . 
C14_1 C 0.07779(19) 0.57349(14) 0.36963(16) 0.0687(7) Uani 1 1 d . . . . . 
H14A_1 H 0.087245 0.544929 0.328245 0.103 Uiso 1 1 calc R U . . . 
H14B_1 H 0.126139 0.619876 0.381482 0.103 Uiso 1 1 calc R U . . . 
H14C_1 H 0.007564 0.594679 0.360014 0.103 Uiso 1 1 calc R U . . . 
C15_1 C 0.42351(11) 0.24343(9) 0.45361(8) 0.0310(3) Uani 1 1 d . . . . . 
C16_1 C 0.44127(11) 0.30376(10) 0.51770(8) 0.0333(3) Uani 1 1 d . . . . . 
C17_1 C 0.41720(13) 0.28835(10) 0.38511(8) 0.0362(3) Uani 1 1 d . . . . . 
H17A_1 H 0.399284 0.248556 0.346516 0.054 Uiso 1 1 calc R U . . . 
H17B_1 H 0.483630 0.313682 0.386684 0.054 Uiso 1 1 calc R U . . . 
H17C_1 H 0.364639 0.331703 0.378088 0.054 Uiso 1 1 calc R U . . . 
C18_1 C 0.49775(13) 0.17126(11) 0.46235(10) 0.0406(4) Uani 1 1 d . . . . . 
H18A_1 H 0.479049 0.135803 0.420867 0.061 Uiso 1 1 calc R U . . . 
H18B_1 H 0.494802 0.138803 0.503472 0.061 Uiso 1 1 calc R U . . . 
H18C_1 H 0.567401 0.192511 0.468349 0.061 Uiso 1 1 calc R U . . . 
C19_1 C 0.49295(14) 0.38531(12) 0.50902(10) 0.0458(4) Uani 1 1 d . . . . . 
H19A_1 H 0.561768 0.374241 0.503804 0.069 Uiso 1 1 calc R U . . . 
H19B_1 H 0.497977 0.420167 0.550196 0.069 Uiso 1 1 calc R U . . . 
H19C_1 H 0.452455 0.414156 0.467477 0.069 Uiso 1 1 calc R U . . . 
C20_1 C 0.49503(14) 0.26349(14) 0.58695(9) 0.0482(4) Uani 1 1 d . . . . . 
H20A_1 H 0.459949 0.211687 0.592468 0.072 Uiso 1 1 calc R U . . . 
H20B_1 H 0.493401 0.301415 0.625192 0.072 Uiso 1 1 calc R U . . . 
H20C_1 H 0.566323 0.251440 0.587757 0.072 Uiso 1 1 calc R U . . . 
B1_1 B 0.27351(13) 0.26373(10) 0.48294(9) 0.0290(3) Uani 1 1 d . . . . . 
  
  
_geom_special_details 
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
; 
  
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 
P1 O1 1.4714(12) . ? 
P1 O2 1.5648(12) . ? 
P1 O3 1.5709(12) . ? 
P1 C1 1.7931(15) . ? 
C1 C2 1.386(2) . ? 
C1 C10 1.439(2) . ? 
C2 C3 1.421(2) . ? 
C2 B1 1.583(2) . ? 
O2 C11 1.463(2) . ? 
C3 C4 1.367(2) . ? 
C3 H3 0.9500 . ? 
O3 C13 1.453(2) . ? 
C4 C5 1.417(2) . ? 
C4 H4 0.9500 . ? 
O4 B1 1.375(2) . ? 
O4 C15 1.4538(18) . ? 
C5 C10 1.423(2) . ? 
C5 C6 1.423(2) . ? 
O5 B1 1.368(2) . ? 
O5 C16 1.4620(18) . ? 
C6 C7 1.367(2) . ? 
C6 H6 0.9500 . ? 
C7 C8 1.408(2) . ? 
C7 H7 0.9500 . ? 
C8 C9 1.373(2) . ? 
C8 H8 0.9500 . ? 
C9 C10 1.419(2) . ? 
C9 H9 0.9500 . ? 
C11 C12 1.492(3) . ? 
C11 H11A 0.9900 . ? 
C11 H11B 0.9900 . ? 
C12 H12A 0.9800 . ? 
C12 H12B 0.9800 . ? 
C12 H12C 0.9800 . ? 
C13 C14 1.499(2) . ? 
C13 H13A 0.9900 . ? 
C13 H13B 0.9900 . ? 
C14 H14A 0.9800 . ? 
C14 H14B 0.9800 . ? 
C14 H14C 0.9800 . ? 
C15 C17 1.516(2) . ? 
C15 C18 1.527(2) . ? 
C15 C16 1.571(2) . ? 
C16 C20 1.520(2) . ? 
C16 C19 1.526(2) . ? 
C17 H17A 0.9800 . ? 
C17 H17B 0.9800 . ? 
C17 H17C 0.9800 . ? 
C18 H18A 0.9800 . ? 
C18 H18B 0.9800 . ? 
C18 H18C 0.9800 . ? 
C19 H19A 0.9800 . ? 
C19 H19B 0.9800 . ? 
C19 H19C 0.9800 . ? 
C20 H20A 0.9800 . ? 
C20 H20B 0.9800 . ? 
C20 H20C 0.9800 . ? 
P1_1 O1_1 1.4691(12) . ? 
P1_1 O3_1 1.5759(12) . ? 
P1_1 O2_1 1.5785(12) . ? 
P1_1 C1_1 1.7902(15) . ? 
O2_1 C11_1 1.460(2) . ? 
O3_1 C13_1 1.448(2) . ? 
O4_1 B1_1 1.366(2) . ? 
O4_1 C15_1 1.4639(17) . ? 
O5_1 B1_1 1.368(2) . ? 
O5_1 C16_1 1.4557(19) . ? 
C1_1 C2_1 1.390(2) . ? 
C1_1 C10_1 1.434(2) . ? 
C2_1 C3_1 1.424(2) . ? 
C2_1 B1_1 1.581(2) . ? 
C3_1 C4_1 1.366(2) . ? 
C3_1 H3_1 0.9500 . ? 
C4_1 C5_1 1.417(2) . ? 
C4_1 H4_1 0.9500 . ? 
C5_1 C6_1 1.420(2) . ? 
C5_1 C10_1 1.429(2) . ? 
C6_1 C7_1 1.366(2) . ? 
C6_1 H6_1 0.9500 . ? 
C7_1 C8_1 1.412(2) . ? 
C7_1 H7_1 0.9500 . ? 
C8_1 C9_1 1.370(2) . ? 
C8_1 H8_1 0.9500 . ? 
C9_1 C10_1 1.421(2) . ? 
C9_1 H9_1 0.9500 . ? 
C11_1 C12_1 1.493(3) . ? 
C11_1 H11A_1 0.9900 . ? 
C11_1 H11B_1 0.9900 . ? 
C12_1 H12A_1 0.9800 . ? 
C12_1 H12B_1 0.9800 . ? 
C12_1 H12C_1 0.9800 . ? 
C13_1 C14_1 1.477(3) . ? 
C13_1 H13A_1 0.9900 . ? 
C13_1 H13B_1 0.9900 . ? 
C14_1 H14A_1 0.9800 . ? 
C14_1 H14B_1 0.9800 . ? 
C14_1 H14C_1 0.9800 . ? 
C15_1 C18_1 1.516(2) . ? 
C15_1 C17_1 1.525(2) . ? 
C15_1 C16_1 1.570(2) . ? 
C16_1 C19_1 1.519(2) . ? 
C16_1 C20_1 1.523(2) . ? 
C17_1 H17A_1 0.9800 . ? 
C17_1 H17B_1 0.9800 . ? 
C17_1 H17C_1 0.9800 . ? 
C18_1 H18A_1 0.9800 . ? 
C18_1 H18B_1 0.9800 . ? 
C18_1 H18C_1 0.9800 . ? 
C19_1 H19A_1 0.9800 . ? 
C19_1 H19B_1 0.9800 . ? 
C19_1 H19C_1 0.9800 . ? 
C20_1 H20A_1 0.9800 . ? 
C20_1 H20B_1 0.9800 . ? 
C20_1 H20C_1 0.9800 . ? 
  
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 
O1 P1 O2 115.47(7) . . ? 
O1 P1 O3 115.91(7) . . ? 
O2 P1 O3 97.47(6) . . ? 
O1 P1 C1 107.72(7) . . ? 
O2 P1 C1 110.57(7) . . ? 
O3 P1 C1 109.37(7) . . ? 
C2 C1 C10 121.73(13) . . ? 
C2 C1 P1 114.04(11) . . ? 
C10 C1 P1 124.17(11) . . ? 
C1 C2 C3 118.64(14) . . ? 
C1 C2 B1 124.02(13) . . ? 
C3 C2 B1 117.30(13) . . ? 
C11 O2 P1 118.47(10) . . ? 
C4 C3 C2 121.14(14) . . ? 
C4 C3 H3 119.4 . . ? 
C2 C3 H3 119.4 . . ? 
C13 O3 P1 120.02(11) . . ? 
C3 C4 C5 121.17(14) . . ? 
C3 C4 H4 119.4 . . ? 
C5 C4 H4 119.4 . . ? 
B1 O4 C15 107.47(12) . . ? 
C4 C5 C10 119.40(14) . . ? 
C4 C5 C6 121.19(14) . . ? 
C10 C5 C6 119.40(14) . . ? 
B1 O5 C16 106.89(12) . . ? 
C7 C6 C5 120.64(15) . . ? 
C7 C6 H6 119.7 . . ? 
C5 C6 H6 119.7 . . ? 
C6 C7 C8 120.00(15) . . ? 
C6 C7 H7 120.0 . . ? 
C8 C7 H7 120.0 . . ? 
C9 C8 C7 120.96(15) . . ? 
C9 C8 H8 119.5 . . ? 
C7 C8 H8 119.5 . . ? 
C8 C9 C10 120.58(15) . . ? 
C8 C9 H9 119.7 . . ? 
C10 C9 H9 119.7 . . ? 
C9 C10 C5 118.41(13) . . ? 
C9 C10 C1 123.65(13) . . ? 
C5 C10 C1 117.92(13) . . ? 
O2 C11 C12 107.99(15) . . ? 
O2 C11 H11A 110.1 . . ? 
C12 C11 H11A 110.1 . . ? 
O2 C11 H11B 110.1 . . ? 
C12 C11 H11B 110.1 . . ? 
H11A C11 H11B 108.4 . . ? 
C11 C12 H12A 109.5 . . ? 
C11 C12 H12B 109.5 . . ? 
H12A C12 H12B 109.5 . . ? 
C11 C12 H12C 109.5 . . ? 
H12A C12 H12C 109.5 . . ? 
H12B C12 H12C 109.5 . . ? 
O3 C13 C14 108.37(14) . . ? 
O3 C13 H13A 110.0 . . ? 
C14 C13 H13A 110.0 . . ? 
O3 C13 H13B 110.0 . . ? 
C14 C13 H13B 110.0 . . ? 
H13A C13 H13B 108.4 . . ? 
C13 C14 H14A 109.5 . . ? 
C13 C14 H14B 109.5 . . ? 
H14A C14 H14B 109.5 . . ? 
C13 C14 H14C 109.5 . . ? 
H14A C14 H14C 109.5 . . ? 
H14B C14 H14C 109.5 . . ? 
O4 C15 C17 108.30(14) . . ? 
O4 C15 C18 106.08(14) . . ? 
C17 C15 C18 110.06(15) . . ? 
O4 C15 C16 103.01(12) . . ? 
C17 C15 C16 114.98(14) . . ? 
C18 C15 C16 113.66(14) . . ? 
O5 C16 C20 107.69(13) . . ? 
O5 C16 C19 107.02(12) . . ? 
C20 C16 C19 110.79(13) . . ? 
O5 C16 C15 102.60(11) . . ? 
C20 C16 C15 114.65(14) . . ? 
C19 C16 C15 113.33(13) . . ? 
C15 C17 H17A 109.5 . . ? 
C15 C17 H17B 109.5 . . ? 
H17A C17 H17B 109.5 . . ? 
C15 C17 H17C 109.5 . . ? 
H17A C17 H17C 109.5 . . ? 
H17B C17 H17C 109.5 . . ? 
C15 C18 H18A 109.5 . . ? 
C15 C18 H18B 109.5 . . ? 
H18A C18 H18B 109.5 . . ? 
C15 C18 H18C 109.5 . . ? 
H18A C18 H18C 109.5 . . ? 
H18B C18 H18C 109.5 . . ? 
C16 C19 H19A 109.5 . . ? 
C16 C19 H19B 109.5 . . ? 
H19A C19 H19B 109.5 . . ? 
C16 C19 H19C 109.5 . . ? 
H19A C19 H19C 109.5 . . ? 
H19B C19 H19C 109.5 . . ? 
C16 C20 H20A 109.5 . . ? 
C16 C20 H20B 109.5 . . ? 
H20A C20 H20B 109.5 . . ? 
C16 C20 H20C 109.5 . . ? 
H20A C20 H20C 109.5 . . ? 
H20B C20 H20C 109.5 . . ? 
O5 B1 O4 113.71(14) . . ? 
O5 B1 C2 121.75(14) . . ? 
O4 B1 C2 121.14(14) . . ? 
O1_1 P1_1 O3_1 115.78(7) . . ? 
O1_1 P1_1 O2_1 115.61(7) . . ? 
O3_1 P1_1 O2_1 99.28(6) . . ? 
O1_1 P1_1 C1_1 110.30(7) . . ? 
O3_1 P1_1 C1_1 107.21(7) . . ? 
O2_1 P1_1 C1_1 107.79(6) . . ? 
C11_1 O2_1 P1_1 118.25(10) . . ? 
C13_1 O3_1 P1_1 122.25(12) . . ? 
B1_1 O4_1 C15_1 107.17(12) . . ? 
B1_1 O5_1 C16_1 107.98(12) . . ? 
C2_1 C1_1 C10_1 121.67(13) . . ? 
C2_1 C1_1 P1_1 115.07(11) . . ? 
C10_1 C1_1 P1_1 123.26(11) . . ? 
C1_1 C2_1 C3_1 118.54(13) . . ? 
C1_1 C2_1 B1_1 125.87(13) . . ? 
C3_1 C2_1 B1_1 115.47(12) . . ? 
C4_1 C3_1 C2_1 121.17(13) . . ? 
C4_1 C3_1 H3_1 119.4 . . ? 
C2_1 C3_1 H3_1 119.4 . . ? 
C3_1 C4_1 C5_1 121.27(14) . . ? 
C3_1 C4_1 H4_1 119.4 . . ? 
C5_1 C4_1 H4_1 119.4 . . ? 
C4_1 C5_1 C6_1 120.98(14) . . ? 
C4_1 C5_1 C10_1 119.17(13) . . ? 
C6_1 C5_1 C10_1 119.84(13) . . ? 
C7_1 C6_1 C5_1 120.36(14) . . ? 
C7_1 C6_1 H6_1 119.8 . . ? 
C5_1 C6_1 H6_1 119.8 . . ? 
C6_1 C7_1 C8_1 120.27(15) . . ? 
C6_1 C7_1 H7_1 119.9 . . ? 
C8_1 C7_1 H7_1 119.9 . . ? 
C9_1 C8_1 C7_1 120.67(15) . . ? 
C9_1 C8_1 H8_1 119.7 . . ? 
C7_1 C8_1 H8_1 119.7 . . ? 
C8_1 C9_1 C10_1 121.02(14) . . ? 
C8_1 C9_1 H9_1 119.5 . . ? 
C10_1 C9_1 H9_1 119.5 . . ? 
C9_1 C10_1 C5_1 117.82(13) . . ? 
C9_1 C10_1 C1_1 124.08(13) . . ? 
C5_1 C10_1 C1_1 118.10(13) . . ? 
O2_1 C11_1 C12_1 108.30(14) . . ? 
O2_1 C11_1 H11A_1 110.0 . . ? 
C12_1 C11_1 H11A_1 110.0 . . ? 
O2_1 C11_1 H11B_1 110.0 . . ? 
C12_1 C11_1 H11B_1 110.0 . . ? 
H11A_1 C11_1 H11B_1 108.4 . . ? 
C11_1 C12_1 H12A_1 109.5 . . ? 
C11_1 C12_1 H12B_1 109.5 . . ? 
H12A_1 C12_1 H12B_1 109.5 . . ? 
C11_1 C12_1 H12C_1 109.5 . . ? 
H12A_1 C12_1 H12C_1 109.5 . . ? 
H12B_1 C12_1 H12C_1 109.5 . . ? 
O3_1 C13_1 C14_1 110.61(19) . . ? 
O3_1 C13_1 H13A_1 109.5 . . ? 
C14_1 C13_1 H13A_1 109.5 . . ? 
O3_1 C13_1 H13B_1 109.5 . . ? 
C14_1 C13_1 H13B_1 109.5 . . ? 
H13A_1 C13_1 H13B_1 108.1 . . ? 
C13_1 C14_1 H14A_1 109.5 . . ? 
C13_1 C14_1 H14B_1 109.5 . . ? 
H14A_1 C14_1 H14B_1 109.5 . . ? 
C13_1 C14_1 H14C_1 109.5 . . ? 
H14A_1 C14_1 H14C_1 109.5 . . ? 
H14B_1 C14_1 H14C_1 109.5 . . ? 
O4_1 C15_1 C18_1 107.83(12) . . ? 
O4_1 C15_1 C17_1 107.03(12) . . ? 
C18_1 C15_1 C17_1 110.24(14) . . ? 
O4_1 C15_1 C16_1 102.72(11) . . ? 
C18_1 C15_1 C16_1 115.21(13) . . ? 
C17_1 C15_1 C16_1 113.09(13) . . ? 
O5_1 C16_1 C19_1 108.02(13) . . ? 
O5_1 C16_1 C20_1 106.13(13) . . ? 
C19_1 C16_1 C20_1 110.25(14) . . ? 
O5_1 C16_1 C15_1 102.91(11) . . ? 
C19_1 C16_1 C15_1 114.82(14) . . ? 
C20_1 C16_1 C15_1 113.91(14) . . ? 
C15_1 C17_1 H17A_1 109.5 . . ? 
C15_1 C17_1 H17B_1 109.5 . . ? 
H17A_1 C17_1 H17B_1 109.5 . . ? 
C15_1 C17_1 H17C_1 109.5 . . ? 
H17A_1 C17_1 H17C_1 109.5 . . ? 
H17B_1 C17_1 H17C_1 109.5 . . ? 
C15_1 C18_1 H18A_1 109.5 . . ? 
C15_1 C18_1 H18B_1 109.5 . . ? 
H18A_1 C18_1 H18B_1 109.5 . . ? 
C15_1 C18_1 H18C_1 109.5 . . ? 
H18A_1 C18_1 H18C_1 109.5 . . ? 
H18B_1 C18_1 H18C_1 109.5 . . ? 
C16_1 C19_1 H19A_1 109.5 . . ? 
C16_1 C19_1 H19B_1 109.5 . . ? 
H19A_1 C19_1 H19B_1 109.5 . . ? 
C16_1 C19_1 H19C_1 109.5 . . ? 
H19A_1 C19_1 H19C_1 109.5 . . ? 
H19B_1 C19_1 H19C_1 109.5 . . ? 
C16_1 C20_1 H20A_1 109.5 . . ? 
C16_1 C20_1 H20B_1 109.5 . . ? 
H20A_1 C20_1 H20B_1 109.5 . . ? 
C16_1 C20_1 H20C_1 109.5 . . ? 
H20A_1 C20_1 H20C_1 109.5 . . ? 
H20B_1 C20_1 H20C_1 109.5 . . ? 
O4_1 B1_1 O5_1 113.63(14) . . ? 
O4_1 B1_1 C2_1 122.99(13) . . ? 
O5_1 B1_1 C2_1 120.97(14) . . ? 
  
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 
O1 P1 C1 C2 2.38(13) . . . . ? 
O2 P1 C1 C2 129.41(11) . . . . ? 
O3 P1 C1 C2 -124.38(11) . . . . ? 
O1 P1 C1 C10 179.50(12) . . . . ? 
O2 P1 C1 C10 -53.47(13) . . . . ? 
O3 P1 C1 C10 52.74(13) . . . . ? 
C10 C1 C2 C3 0.6(2) . . . . ? 
P1 C1 C2 C3 177.80(11) . . . . ? 
C10 C1 C2 B1 -176.89(13) . . . . ? 
P1 C1 C2 B1 0.30(18) . . . . ? 
O1 P1 O2 C11 47.79(14) . . . . ? 
O3 P1 O2 C11 171.20(12) . . . . ? 
C1 P1 O2 C11 -74.81(13) . . . . ? 
C1 C2 C3 C4 -1.0(2) . . . . ? 
B1 C2 C3 C4 176.70(14) . . . . ? 
O1 P1 O3 C13 -45.62(15) . . . . ? 
O2 P1 O3 C13 -168.71(13) . . . . ? 
C1 P1 O3 C13 76.35(14) . . . . ? 
C2 C3 C4 C5 0.3(2) . . . . ? 
C3 C4 C5 C10 0.6(2) . . . . ? 
C3 C4 C5 C6 -178.26(15) . . . . ? 
C4 C5 C6 C7 178.65(15) . . . . ? 
C10 C5 C6 C7 -0.3(2) . . . . ? 
C5 C6 C7 C8 0.7(2) . . . . ? 
C6 C7 C8 C9 -0.4(2) . . . . ? 
C7 C8 C9 C10 -0.5(2) . . . . ? 
C8 C9 C10 C5 1.0(2) . . . . ? 
C8 C9 C10 C1 -177.49(14) . . . . ? 
C4 C5 C10 C9 -179.51(14) . . . . ? 
C6 C5 C10 C9 -0.6(2) . . . . ? 
C4 C5 C10 C1 -1.0(2) . . . . ? 
C6 C5 C10 C1 177.96(13) . . . . ? 
C2 C1 C10 C9 178.81(14) . . . . ? 
P1 C1 C10 C9 1.9(2) . . . . ? 
C2 C1 C10 C5 0.3(2) . . . . ? 
P1 C1 C10 C5 -176.56(11) . . . . ? 
P1 O2 C11 C12 118.34(15) . . . . ? 
P1 O3 C13 C14 136.11(14) . . . . ? 
B1 O4 C15 C17 140.15(14) . . . . ? 
B1 O4 C15 C18 -101.73(16) . . . . ? 
B1 O4 C15 C16 17.96(16) . . . . ? 
B1 O5 C16 C20 143.78(14) . . . . ? 
B1 O5 C16 C19 -97.07(14) . . . . ? 
B1 O5 C16 C15 22.46(15) . . . . ? 
O4 C15 C16 O5 -24.43(14) . . . . ? 
C17 C15 C16 O5 -142.02(13) . . . . ? 
C18 C15 C16 O5 89.88(15) . . . . ? 
O4 C15 C16 C20 -140.86(14) . . . . ? 
C17 C15 C16 C20 101.55(17) . . . . ? 
C18 C15 C16 C20 -26.6(2) . . . . ? 
O4 C15 C16 C19 90.60(15) . . . . ? 
C17 C15 C16 C19 -26.99(19) . . . . ? 
C18 C15 C16 C19 -155.10(15) . . . . ? 
C16 O5 B1 O4 -12.55(18) . . . . ? 
C16 O5 B1 C2 -171.93(13) . . . . ? 
C15 O4 B1 O5 -4.41(18) . . . . ? 
C15 O4 B1 C2 155.11(14) . . . . ? 
C1 C2 B1 O5 -106.16(18) . . . . ? 
C3 C2 B1 O5 76.31(19) . . . . ? 
C1 C2 B1 O4 95.97(19) . . . . ? 
C3 C2 B1 O4 -81.55(19) . . . . ? 
O1_1 P1_1 O2_1 C11_1 57.88(13) . . . . ? 
O3_1 P1_1 O2_1 C11_1 -177.58(11) . . . . ? 
C1_1 P1_1 O2_1 C11_1 -66.02(13) . . . . ? 
O1_1 P1_1 O3_1 C13_1 -10.54(16) . . . . ? 
O2_1 P1_1 O3_1 C13_1 -134.97(14) . . . . ? 
C1_1 P1_1 O3_1 C13_1 113.03(14) . . . . ? 
O1_1 P1_1 C1_1 C2_1 -0.59(13) . . . . ? 
O3_1 P1_1 C1_1 C2_1 -127.47(11) . . . . ? 
O2_1 P1_1 C1_1 C2_1 126.47(11) . . . . ? 
O1_1 P1_1 C1_1 C10_1 178.76(12) . . . . ? 
O3_1 P1_1 C1_1 C10_1 51.89(13) . . . . ? 
O2_1 P1_1 C1_1 C10_1 -54.18(13) . . . . ? 
C10_1 C1_1 C2_1 C3_1 1.1(2) . . . . ? 
P1_1 C1_1 C2_1 C3_1 -179.53(11) . . . . ? 
C10_1 C1_1 C2_1 B1_1 -174.85(13) . . . . ? 
P1_1 C1_1 C2_1 B1_1 4.52(19) . . . . ? 
C1_1 C2_1 C3_1 C4_1 -2.2(2) . . . . ? 
B1_1 C2_1 C3_1 C4_1 174.13(13) . . . . ? 
C2_1 C3_1 C4_1 C5_1 0.7(2) . . . . ? 
C3_1 C4_1 C5_1 C6_1 -179.05(14) . . . . ? 
C3_1 C4_1 C5_1 C10_1 2.1(2) . . . . ? 
C4_1 C5_1 C6_1 C7_1 -177.43(15) . . . . ? 
C10_1 C5_1 C6_1 C7_1 1.5(2) . . . . ? 
C5_1 C6_1 C7_1 C8_1 -0.3(2) . . . . ? 
C6_1 C7_1 C8_1 C9_1 -0.7(3) . . . . ? 
C7_1 C8_1 C9_1 C10_1 0.4(3) . . . . ? 
C8_1 C9_1 C10_1 C5_1 0.8(2) . . . . ? 
C8_1 C9_1 C10_1 C1_1 -178.88(15) . . . . ? 
C4_1 C5_1 C10_1 C9_1 177.20(13) . . . . ? 
C6_1 C5_1 C10_1 C9_1 -1.7(2) . . . . ? 
C4_1 C5_1 C10_1 C1_1 -3.1(2) . . . . ? 
C6_1 C5_1 C10_1 C1_1 178.00(13) . . . . ? 
C2_1 C1_1 C10_1 C9_1 -178.78(14) . . . . ? 
P1_1 C1_1 C10_1 C9_1 1.9(2) . . . . ? 
C2_1 C1_1 C10_1 C5_1 1.5(2) . . . . ? 
P1_1 C1_1 C10_1 C5_1 -177.78(10) . . . . ? 
P1_1 O2_1 C11_1 C12_1 150.58(12) . . . . ? 
P1_1 O3_1 C13_1 C14_1 105.27(18) . . . . ? 
B1_1 O4_1 C15_1 C18_1 143.42(13) . . . . ? 
B1_1 O4_1 C15_1 C17_1 -97.99(14) . . . . ? 
B1_1 O4_1 C15_1 C16_1 21.33(14) . . . . ? 
B1_1 O5_1 C16_1 C19_1 138.51(14) . . . . ? 
B1_1 O5_1 C16_1 C20_1 -103.26(15) . . . . ? 
B1_1 O5_1 C16_1 C15_1 16.68(15) . . . . ? 
O4_1 C15_1 C16_1 O5_1 -22.84(14) . . . . ? 
C18_1 C15_1 C16_1 O5_1 -139.79(13) . . . . ? 
C17_1 C15_1 C16_1 O5_1 92.16(14) . . . . ? 
O4_1 C15_1 C16_1 C19_1 -139.95(14) . . . . ? 
C18_1 C15_1 C16_1 C19_1 103.09(17) . . . . ? 
C17_1 C15_1 C16_1 C19_1 -24.95(19) . . . . ? 
O4_1 C15_1 C16_1 C20_1 91.58(15) . . . . ? 
C18_1 C15_1 C16_1 C20_1 -25.38(19) . . . . ? 
C17_1 C15_1 C16_1 C20_1 -153.43(14) . . . . ? 
C15_1 O4_1 B1_1 O5_1 -12.16(17) . . . . ? 
C15_1 O4_1 B1_1 C2_1 -174.65(13) . . . . ? 
C16_1 O5_1 B1_1 O4_1 -3.79(18) . . . . ? 
C16_1 O5_1 B1_1 C2_1 159.09(13) . . . . ? 
C1_1 C2_1 B1_1 O4_1 -107.78(18) . . . . ? 
C3_1 C2_1 B1_1 O4_1 76.16(18) . . . . ? 
C1_1 C2_1 B1_1 O5_1 90.98(19) . . . . ? 
C3_1 C2_1 B1_1 O5_1 -85.08(18) . . . . ? 
  
_refine_diff_density_max    0.495 
_refine_diff_density_min   -0.334 
_refine_diff_density_rms    0.046 
  
  
  
