#------------------------------------------------------------------------------
#$Date: 2023-11-21 00:57:42 +0200 (Tue, 21 Nov 2023) $
#$Revision: 287692 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/23/7132373.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_7132373
loop_
_publ_author_name
'Leinauer, Luisa'
'Parla, Giorgio'
'Messelbeger, Julian'
'Herrera, Alberto'
'Heinemann, Frank W.'
'Langer, Jens'
'Chuchelkin, Ilya'
'Grasruck, Alexander'
'Frieß, Sibylle'
'Chelouan, Ahmed'
'Gavrilov, Konstantin'
'Dorta, Romano'
_publ_section_title
;
 Evolution of a 'privileged' P-alkene ligand: added planar chirality beats
 BINOL axial chirality in catalytic asymmetric C-C bond formation.
;
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_paper_doi               10.1039/d3cc04972h
_journal_year                    2023
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C40 H29 B N O2 P'
_chemical_formula_sum            'C40 H29 B N O2 P'
_chemical_formula_weight         597.42
_space_group_crystal_system      trigonal
_space_group_IT_number           146
_space_group_name_Hall           'R 3'
_space_group_name_H-M_alt        'R 3 :H'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2023-07-07
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_audit_update_record
;
2023-09-18 deposited with the CCDC.	2023-10-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            9
_cell_length_a                   28.285(3)
_cell_length_b                   28.285(3)
_cell_length_c                   10.0973(12)
_cell_measurement_reflns_used    9938
_cell_measurement_temperature    100.15
_cell_measurement_theta_max      26.53
_cell_measurement_theta_min      2.18
_cell_volume                     6996.0(13)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'SHELXTL 6.12 (Bruker AXS, 2002)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELX XT 2014/5 (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 83.33
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker Kappa APEX II'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Quazar focussing montel optics'
_diffrn_radiation_source         'ImuS high brilliance micro-focus tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1167
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       35
_diffrn_reflns_limit_k_min       -35
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            67265
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.182
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.126
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.4761
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1375 before and 0.0882 after correction.
The Ratio of minimum to maximum transmission is 0.6386.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.276
_exptl_crystal_description       needle
_exptl_crystal_F_000             2808
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: toluene, n-pentane, 1,2-difluorobenzene'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.413
_refine_diff_density_rms         0.063
_refine_ls_abs_structure_details
;
 Flack x determined using 2566 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.210
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     415
_refine_ls_number_reflns         6374
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.210
_refine_ls_R_factor_all          0.0683
_refine_ls_R_factor_gt           0.0589
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0129P)²+28.0760P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1241
_refine_ls_wR_factor_ref         0.1294
_reflns_Friedel_coverage         1.000
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                5839
_reflns_number_total             6374
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3cc04972h2.cif
_cod_data_source_block           rd1723
_cod_original_cell_volume        6996.0(15)
_cod_original_sg_symbol_H-M      'R 3'
_cod_database_code               7132373
_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_max   0.991
_shelx_estimated_absorpt_t_min   0.966
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All B(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C8(H8), C10(H10), C11(H11), C12(H12),
 C13(H13), C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23),
  C25(H25), C26(H26), C27(H27), C28(H28), C33(H33), C34(H34), C35(H35),
 C36(H36), C38(H38), C39(H39)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
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 0.21601(5) 0.36050(5) 0.47349(12) 0.0174(3) Uani 1 1 d . . . . .
O1 O 0.15688(13) 0.35294(14) 0.5018(3) 0.0181(7) Uani 1 1 d . . . . .
O2 O 0.20230(14) 0.30600(14) 0.3918(3) 0.0189(7) Uani 1 1 d . . . . .
N1 N 0.23426(16) 0.35911(17) 0.6260(4) 0.0193(9) Uani 1 1 d . . . . .
B1 B 0.2643(3) 0.4212(3) 0.3705(6) 0.0239(13) Uani 1 1 d . . . . .
H1A H 0.243(3) 0.411(2) 0.274(6) 0.036 Uiso 1 1 d . U . . .
H1B H 0.262(2) 0.452(2) 0.437(6) 0.036 Uiso 1 1 d . U . . .
H1C H 0.308(3) 0.419(2) 0.378(6) 0.036 Uiso 1 1 d . U . . .
C1 C 0.2915(2) 0.3801(2) 0.6568(5) 0.0194(10) Uani 1 1 d . . . . .
C2 C 0.3144(2) 0.3480(2) 0.6266(5) 0.0202(11) Uani 1 1 d . . . . .
H2 H 0.292975 0.313194 0.586950 0.024 Uiso 1 1 calc R U . . .
C3 C 0.3690(2) 0.3675(2) 0.6552(5) 0.0250(12) Uani 1 1 d . . . . .
H3 H 0.385276 0.346217 0.633081 0.030 Uiso 1 1 calc R U . . .
C4 C 0.3997(2) 0.4175(2) 0.7155(5) 0.0281(12) Uani 1 1 d . . . . .
H4 H 0.436860 0.430260 0.737306 0.034 Uiso 1 1 calc R U . . .
C5 C 0.3764(2) 0.4491(2) 0.7442(5) 0.0260(12) Uani 1 1 d . . . . .
H5 H 0.398079 0.483900 0.783924 0.031 Uiso 1 1 calc R U . . .
C6 C 0.3213(2) 0.4311(2) 0.7161(5) 0.0205(11) Uani 1 1 d . . . . .
C7 C 0.2969(2) 0.4640(2) 0.7582(5) 0.0261(12) Uani 1 1 d . . . . .
C8 C 0.2459(2) 0.4425(2) 0.8074(5) 0.0278(12) Uani 1 1 d . . . . .
H8 H 0.235618 0.468353 0.834324 0.033 Uiso 1 1 calc R U . . .
C9 C 0.2042(2) 0.3853(2) 0.8252(5) 0.0270(12) Uani 1 1 d . . . . .
C10 C 0.1676(3) 0.3709(3) 0.9294(6) 0.0370(15) Uani 1 1 d . . . . .
H10 H 0.170161 0.398455 0.987836 0.044 Uiso 1 1 calc R U . . .
C11 C 0.1276(3) 0.3176(3) 0.9496(7) 0.0450(18) Uani 1 1 d . . . . .
H11 H 0.102591 0.308730 1.020843 0.054 Uiso 1 1 calc R U . . .
C12 C 0.1236(3) 0.2769(3) 0.8673(6) 0.0398(16) Uani 1 1 d . . . . .
H12 H 0.096471 0.239926 0.882641 0.048 Uiso 1 1 calc R U . . .
C13 C 0.1592(2) 0.2902(2) 0.7624(6) 0.0286(12) Uani 1 1 d . . . . .
H13 H 0.156673 0.262379 0.705268 0.034 Uiso 1 1 calc R U . . .
C14 C 0.1989(2) 0.3445(2) 0.7400(5) 0.0237(11) Uani 1 1 d . . . . .
C15 C 0.3326(2) 0.5249(3) 0.7533(6) 0.0341(14) Uani 1 1 d . . . . .
C16 C 0.3597(2) 0.5498(2) 0.6379(7) 0.0366(15) Uani 1 1 d . . . . .
H16 H 0.357561 0.528200 0.563650 0.044 Uiso 1 1 calc R U . . .
C17 C 0.3905(3) 0.6071(3) 0.6295(8) 0.0482(19) Uani 1 1 d . . . . .
H17 H 0.408428 0.624098 0.549174 0.058 Uiso 1 1 calc R U . . .
C18 C 0.3947(3) 0.6383(3) 0.7379(10) 0.058(2) Uani 1 1 d . . . . .
H18 H 0.415143 0.676987 0.731651 0.069 Uiso 1 1 calc R U . . .
C19 C 0.3695(3) 0.6140(3) 0.8559(9) 0.053(2) Uani 1 1 d . . . . .
H19 H 0.373571 0.635848 0.931225 0.063 Uiso 1 1 calc R U . . .
C20 C 0.3378(3) 0.5569(3) 0.8640(8) 0.0432(17) Uani 1 1 d . . . . .
H20 H 0.319995 0.539986 0.944498 0.052 Uiso 1 1 calc R U . . .
C21 C 0.1181(2) 0.3347(2) 0.4002(5) 0.0191(10) Uani 1 1 d . . . . .
C22 C 0.1044(2) 0.3729(2) 0.3488(5) 0.0215(11) Uani 1 1 d . . . . .
H22 H 0.123185 0.409790 0.377945 0.026 Uiso 1 1 calc R U . . .
C23 C 0.0642(2) 0.3561(2) 0.2574(5) 0.0227(11) Uani 1 1 d . . . . .
H23 H 0.053464 0.380942 0.225933 0.027 Uiso 1 1 calc R U . . .
C24 C 0.0379(2) 0.3020(2) 0.2080(5) 0.0225(11) Uani 1 1 d . . . . .
C25 C -0.0028(2) 0.2846(3) 0.1096(6) 0.0288(13) Uani 1 1 d . . . . .
H25 H -0.015948 0.308195 0.083311 0.035 Uiso 1 1 calc R U . . .
C26 C -0.0234(2) 0.2351(3) 0.0521(6) 0.0326(14) Uani 1 1 d . . . . .
H26 H -0.051044 0.223953 -0.013407 0.039 Uiso 1 1 calc R U . . .
C27 C -0.0037(2) 0.2001(2) 0.0897(6) 0.0292(13) Uani 1 1 d . . . . .
H27 H -0.016624 0.166229 0.045105 0.035 Uiso 1 1 calc R U . . .
C28 C 0.0335(2) 0.2141(2) 0.1891(6) 0.0255(12) Uani 1 1 d . . . . .
H28 H 0.045413 0.189463 0.215201 0.031 Uiso 1 1 calc R U . . .
C29 C 0.0547(2) 0.2652(2) 0.2541(5) 0.0198(11) Uani 1 1 d . . . . .
C30 C 0.0933(2) 0.2815(2) 0.3602(5) 0.0166(10) Uani 1 1 d . . . . .
C31 C 0.1071(2) 0.24258(19) 0.4229(5) 0.0172(10) Uani 1 1 d . . . . .
C32 C 0.0661(2) 0.1920(2) 0.4776(5) 0.0232(12) Uani 1 1 d . . . . .
C33 C 0.0103(2) 0.1778(2) 0.4867(6) 0.0261(12) Uani 1 1 d . . . . .
H33 H -0.000714 0.201824 0.450655 0.031 Uiso 1 1 calc R U . . .
C34 C -0.0275(2) 0.1308(2) 0.5456(7) 0.0393(16) Uani 1 1 d . . . . .
H34 H -0.064563 0.122096 0.549116 0.047 Uiso 1 1 calc R U . . .
C35 C -0.0122(3) 0.0952(3) 0.6013(10) 0.064(3) Uani 1 1 d . . . . .
H35 H -0.038684 0.062681 0.643712 0.077 Uiso 1 1 calc R U . . .
C36 C 0.0407(3) 0.1071(3) 0.5946(9) 0.054(2) Uani 1 1 d . . . . .
H36 H 0.050561 0.082389 0.631725 0.065 Uiso 1 1 calc R U . . .
C37 C 0.0812(2) 0.1556(2) 0.5336(7) 0.0324(14) Uani 1 1 d . . . . .
C38 C 0.1366(2) 0.1695(2) 0.5316(6) 0.0305(13) Uani 1 1 d . . . . .
H38 H 0.146782 0.144430 0.564514 0.037 Uiso 1 1 calc R U . . .
C39 C 0.1756(2) 0.2186(2) 0.4829(6) 0.0256(12) Uani 1 1 d . . . . .
H39 H 0.212901 0.227947 0.482783 0.031 Uiso 1 1 calc R U . . .
C40 C 0.1604(2) 0.2549(2) 0.4335(5) 0.0177(10) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
B B 0.0013 0.0007 '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'
P P 0.1023 0.0942 '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
O1 P1 O2 103.14(18) . . ?
O1 P1 N1 98.6(2) . . ?
O1 P1 B1 117.0(2) . . ?
O2 P1 N1 112.8(2) . . ?
O2 P1 B1 107.8(2) . . ?
N1 P1 B1 116.7(3) . . ?
C21 O1 P1 119.5(3) . . ?
C40 O2 P1 120.5(3) . . ?
C1 N1 P1 119.6(3) . . ?
C14 N1 P1 125.3(3) . . ?
C14 N1 C1 114.6(4) . . ?
P1 B1 H1A 101(3) . . ?
P1 B1 H1B 94(3) . . ?
P1 B1 H1C 102(3) . . ?
H1A B1 H1B 121(5) . . ?
H1A B1 H1C 117(4) . . ?
H1B B1 H1C 115(4) . . ?
C2 C1 N1 118.4(5) . . ?
C2 C1 C6 122.3(5) . . ?
C6 C1 N1 119.4(4) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 C1 119.1(5) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.4(5) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 120.1 . . ?
C3 C4 C5 119.7(5) . . ?
C5 C4 H4 120.1 . . ?
C4 C5 H5 119.2 . . ?
C4 C5 C6 121.7(5) . . ?
C6 C5 H5 119.2 . . ?
C1 C6 C5 116.8(5) . . ?
C1 C6 C7 123.2(5) . . ?
C5 C6 C7 119.8(5) . . ?
C6 C7 C15 117.2(5) . . ?
C8 C7 C6 123.8(5) . . ?
C8 C7 C15 118.8(5) . . ?
C7 C8 H8 115.4 . . ?
C7 C8 C9 129.2(5) . . ?
C9 C8 H8 115.4 . . ?
C10 C9 C8 119.3(6) . . ?
C10 C9 C14 118.2(6) . . ?
C14 C9 C8 122.5(5) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.2(6) . . ?
C11 C10 H10 119.4 . . ?
C10 C11 H11 119.8 . . ?
C10 C11 C12 120.4(6) . . ?
C12 C11 H11 119.8 . . ?
C11 C12 H12 120.3 . . ?
C13 C12 C11 119.4(6) . . ?
C13 C12 H12 120.3 . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.2(6) . . ?
C14 C13 H13 119.9 . . ?
C9 C14 N1 119.0(5) . . ?
C9 C14 C13 120.5(5) . . ?
C13 C14 N1 120.5(5) . . ?
C16 C15 C7 119.8(5) . . ?
C16 C15 C20 119.6(6) . . ?
C20 C15 C7 120.6(6) . . ?
C15 C16 H16 119.8 . . ?
C15 C16 C17 120.3(6) . . ?
C17 C16 H16 119.8 . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.8(8) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 119.7 . . ?
C17 C18 C19 120.6(7) . . ?
C19 C18 H18 119.7 . . ?
C18 C19 H19 120.1 . . ?
C18 C19 C20 119.7(7) . . ?
C20 C19 H19 120.1 . . ?
C15 C20 C19 119.8(8) . . ?
C15 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
O1 C21 C22 116.9(5) . . ?
C30 C21 O1 119.9(4) . . ?
C30 C21 C22 123.1(5) . . ?
C21 C22 H22 120.5 . . ?
C23 C22 C21 118.9(5) . . ?
C23 C22 H22 120.5 . . ?
C22 C23 H23 119.4 . . ?
C22 C23 C24 121.1(5) . . ?
C24 C23 H23 119.4 . . ?
C23 C24 C29 119.2(5) . . ?
C25 C24 C23 121.5(5) . . ?
C25 C24 C29 119.3(5) . . ?
C24 C25 H25 119.4 . . ?
C26 C25 C24 121.3(5) . . ?
C26 C25 H25 119.4 . . ?
C25 C26 H26 120.1 . . ?
C25 C26 C27 119.8(5) . . ?
C27 C26 H26 120.1 . . ?
C26 C27 H27 119.6 . . ?
C28 C27 C26 120.8(6) . . ?
C28 C27 H27 119.6 . . ?
C27 C28 H28 119.7 . . ?
C27 C28 C29 120.5(5) . . ?
C29 C28 H28 119.7 . . ?
C24 C29 C30 119.4(5) . . ?
C28 C29 C24 118.0(5) . . ?
C28 C29 C30 122.6(5) . . ?
C21 C30 C29 117.7(4) . . ?
C21 C30 C31 120.8(4) . . ?
C29 C30 C31 121.5(4) . . ?
C32 C31 C30 121.8(4) . . ?
C40 C31 C30 120.6(4) . . ?
C40 C31 C32 117.6(4) . . ?
C33 C32 C31 122.5(5) . . ?
C37 C32 C31 119.7(5) . . ?
C37 C32 C33 117.7(5) . . ?
C32 C33 H33 119.2 . . ?
C34 C33 C32 121.6(5) . . ?
C34 C33 H33 119.2 . . ?
C33 C34 H34 119.8 . . ?
C33 C34 C35 120.3(6) . . ?
C35 C34 H34 119.8 . . ?
C34 C35 H35 120.0 . . ?
C36 C35 C34 120.0(6) . . ?
C36 C35 H35 120.0 . . ?
C35 C36 H36 119.4 . . ?
C35 C36 C37 121.3(6) . . ?
C37 C36 H36 119.4 . . ?
C36 C37 C32 119.1(5) . . ?
C38 C37 C32 119.1(5) . . ?
C38 C37 C36 121.7(5) . . ?
C37 C38 H38 119.6 . . ?
C39 C38 C37 120.8(5) . . ?
C39 C38 H38 119.6 . . ?
C38 C39 H39 120.3 . . ?
C38 C39 C40 119.3(5) . . ?
C40 C39 H39 120.3 . . ?
C31 C40 O2 119.6(4) . . ?
C31 C40 C39 123.3(5) . . ?
C39 C40 O2 117.1(4) . . ?
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 1.602(3) . ?
P1 O2 1.615(4) . ?
P1 N1 1.630(4) . ?
P1 B1 1.884(6) . ?
O1 C21 1.399(6) . ?
O2 C40 1.400(6) . ?
N1 C1 1.453(6) . ?
N1 C14 1.443(6) . ?
B1 H1A 1.10(6) . ?
B1 H1B 1.12(6) . ?
B1 H1C 1.25(6) . ?
C1 C2 1.387(7) . ?
C1 C6 1.389(7) . ?
C2 H2 0.9500 . ?
C2 C3 1.385(7) . ?
C3 H3 0.9500 . ?
C3 C4 1.378(8) . ?
C4 H4 0.9500 . ?
C4 C5 1.382(8) . ?
C5 H5 0.9500 . ?
C5 C6 1.404(7) . ?
C6 C7 1.473(7) . ?
C7 C8 1.349(8) . ?
C7 C15 1.502(8) . ?
C8 H8 0.9500 . ?
C8 C9 1.461(8) . ?
C9 C10 1.387(8) . ?
C9 C14 1.388(8) . ?
C10 H10 0.9500 . ?
C10 C11 1.376(10) . ?
C11 H11 0.9500 . ?
C11 C12 1.378(10) . ?
C12 H12 0.9500 . ?
C12 C13 1.378(8) . ?
C13 H13 0.9500 . ?
C13 C14 1.394(8) . ?
C15 C16 1.380(9) . ?
C15 C20 1.397(8) . ?
C16 H16 0.9500 . ?
C16 C17 1.406(9) . ?
C17 H17 0.9500 . ?
C17 C18 1.374(10) . ?
C18 H18 0.9500 . ?
C18 C19 1.383(12) . ?
C19 H19 0.9500 . ?
C19 C20 1.404(10) . ?
C20 H20 0.9500 . ?
C21 C22 1.415(7) . ?
C21 C30 1.365(7) . ?
C22 H22 0.9500 . ?
C22 C23 1.352(8) . ?
C23 H23 0.9500 . ?
C23 C24 1.416(8) . ?
C24 C25 1.409(8) . ?
C24 C29 1.420(7) . ?
C25 H25 0.9500 . ?
C25 C26 1.349(9) . ?
C26 H26 0.9500 . ?
C26 C27 1.410(8) . ?
C27 H27 0.9500 . ?
C27 C28 1.363(8) . ?
C28 H28 0.9500 . ?
C28 C29 1.419(8) . ?
C29 C30 1.432(7) . ?
C30 C31 1.482(6) . ?
C31 C32 1.427(7) . ?
C31 C40 1.372(7) . ?
C32 C33 1.423(7) . ?
C32 C37 1.416(7) . ?
C33 H33 0.9500 . ?
C33 C34 1.358(8) . ?
C34 H34 0.9500 . ?
C34 C35 1.398(9) . ?
C35 H35 0.9500 . ?
C35 C36 1.359(9) . ?
C36 H36 0.9500 . ?
C36 C37 1.415(9) . ?
C37 C38 1.412(8) . ?
C38 H38 0.9500 . ?
C38 C39 1.362(8) . ?
C39 H39 0.9500 . ?
C39 C40 1.389(7) . ?
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
P1 O1 C21 C22 -110.8(4) . . . . ?
P1 O1 C21 C30 72.7(5) . . . . ?
P1 O2 C40 C31 69.7(5) . . . . ?
P1 O2 C40 C39 -111.0(5) . . . . ?
P1 N1 C1 C2 -77.2(5) . . . . ?
P1 N1 C1 C6 103.3(5) . . . . ?
P1 N1 C14 C9 -105.3(5) . . . . ?
P1 N1 C14 C13 73.1(6) . . . . ?
O1 P1 O2 C40 -44.8(4) . . . . ?
O1 P1 N1 C1 -162.1(4) . . . . ?
O1 P1 N1 C14 10.0(5) . . . . ?
O1 C21 C22 C23 -175.1(4) . . . . ?
O1 C21 C30 C29 -178.9(4) . . . . ?
O1 C21 C30 C31 -0.2(7) . . . . ?
O2 P1 O1 C21 -44.2(4) . . . . ?
O2 P1 N1 C1 89.7(4) . . . . ?
O2 P1 N1 C14 -98.3(4) . . . . ?
N1 P1 O1 C21 -160.1(4) . . . . ?
N1 P1 O2 C40 60.6(4) . . . . ?
N1 C1 C2 C3 179.9(4) . . . . ?
N1 C1 C6 C5 179.7(4) . . . . ?
N1 C1 C6 C7 4.3(7) . . . . ?
B1 P1 O1 C21 73.9(4) . . . . ?
B1 P1 O2 C40 -169.2(4) . . . . ?
B1 P1 N1 C1 -36.0(5) . . . . ?
B1 P1 N1 C14 136.1(4) . . . . ?
C1 N1 C14 C9 67.2(6) . . . . ?
C1 N1 C14 C13 -114.5(5) . . . . ?
C1 C2 C3 C4 1.5(8) . . . . ?
C1 C6 C7 C8 35.0(8) . . . . ?
C1 C6 C7 C15 -148.9(5) . . . . ?
C2 C1 C6 C5 0.2(7) . . . . ?
C2 C1 C6 C7 -175.2(5) . . . . ?
C2 C3 C4 C5 -1.8(8) . . . . ?
C3 C4 C5 C6 1.4(8) . . . . ?
C4 C5 C6 C1 -0.6(8) . . . . ?
C4 C5 C6 C7 174.9(5) . . . . ?
C5 C6 C7 C8 -140.3(6) . . . . ?
C5 C6 C7 C15 35.8(7) . . . . ?
C6 C1 C2 C3 -0.7(7) . . . . ?
C6 C7 C8 C9 -2.5(9) . . . . ?
C6 C7 C15 C16 52.8(7) . . . . ?
C6 C7 C15 C20 -128.4(6) . . . . ?
C7 C8 C9 C10 148.4(6) . . . . ?
C7 C8 C9 C14 -32.8(9) . . . . ?
C7 C15 C16 C17 176.1(5) . . . . ?
C7 C15 C20 C19 -177.3(5) . . . . ?
C8 C7 C15 C16 -130.9(6) . . . . ?
C8 C7 C15 C20 47.9(8) . . . . ?
C8 C9 C10 C11 179.9(6) . . . . ?
C8 C9 C14 N1 -2.9(8) . . . . ?
C8 C9 C14 C13 178.7(5) . . . . ?
C9 C10 C11 C12 1.0(10) . . . . ?
C10 C9 C14 N1 175.9(5) . . . . ?
C10 C9 C14 C13 -2.5(8) . . . . ?
C10 C11 C12 C13 -1.5(10) . . . . ?
C11 C12 C13 C14 0.0(9) . . . . ?
C12 C13 C14 N1 -176.3(5) . . . . ?
C12 C13 C14 C9 2.0(8) . . . . ?
C14 N1 C1 C2 109.9(5) . . . . ?
C14 N1 C1 C6 -69.6(6) . . . . ?
C14 C9 C10 C11 1.0(9) . . . . ?
C15 C7 C8 C9 -178.6(5) . . . . ?
C15 C16 C17 C18 1.6(10) . . . . ?
C16 C15 C20 C19 1.6(9) . . . . ?
C16 C17 C18 C19 0.9(10) . . . . ?
C17 C18 C19 C20 -2.1(10) . . . . ?
C18 C19 C20 C15 0.8(10) . . . . ?
C20 C15 C16 C17 -2.8(9) . . . . ?
C21 C22 C23 C24 -3.4(7) . . . . ?
C21 C30 C31 C32 126.3(6) . . . . ?
C21 C30 C31 C40 -51.9(7) . . . . ?
C22 C21 C30 C29 4.8(7) . . . . ?
C22 C21 C30 C31 -176.5(5) . . . . ?
C22 C23 C24 C25 -177.9(5) . . . . ?
C22 C23 C24 C29 -0.9(7) . . . . ?
C23 C24 C25 C26 172.4(5) . . . . ?
C23 C24 C29 C28 -170.8(5) . . . . ?
C23 C24 C29 C30 7.1(7) . . . . ?
C24 C25 C26 C27 -0.6(8) . . . . ?
C24 C29 C30 C21 -8.9(7) . . . . ?
C24 C29 C30 C31 172.4(4) . . . . ?
C25 C24 C29 C28 6.3(7) . . . . ?
C25 C24 C29 C30 -175.8(5) . . . . ?
C25 C26 C27 C28 4.0(9) . . . . ?
C26 C27 C28 C29 -2.1(8) . . . . ?
C27 C28 C29 C24 -3.0(7) . . . . ?
C27 C28 C29 C30 179.2(5) . . . . ?
C28 C29 C30 C21 168.9(5) . . . . ?
C28 C29 C30 C31 -9.8(7) . . . . ?
C29 C24 C25 C26 -4.6(8) . . . . ?
C29 C30 C31 C32 -55.1(7) . . . . ?
C29 C30 C31 C40 126.8(5) . . . . ?
C30 C21 C22 C23 1.3(8) . . . . ?
C30 C31 C32 C33 -5.9(8) . . . . ?
C30 C31 C32 C37 178.4(5) . . . . ?
C30 C31 C40 O2 3.8(7) . . . . ?
C30 C31 C40 C39 -175.5(5) . . . . ?
C31 C32 C33 C34 -176.3(6) . . . . ?
C31 C32 C37 C36 176.2(6) . . . . ?
C31 C32 C37 C38 -1.3(9) . . . . ?
C32 C31 C40 O2 -174.4(4) . . . . ?
C32 C31 C40 C39 6.3(8) . . . . ?
C32 C33 C34 C35 1.0(11) . . . . ?
C32 C37 C38 C39 3.4(9) . . . . ?
C33 C32 C37 C36 0.3(9) . . . . ?
C33 C32 C37 C38 -177.2(6) . . . . ?
C33 C34 C35 C36 -1.1(13) . . . . ?
C34 C35 C36 C37 0.8(14) . . . . ?
C35 C36 C37 C32 -0.5(12) . . . . ?
C35 C36 C37 C38 177.0(8) . . . . ?
C36 C37 C38 C39 -174.1(7) . . . . ?
C37 C32 C33 C34 -0.6(9) . . . . ?
C37 C38 C39 C40 -0.7(9) . . . . ?
C38 C39 C40 O2 176.4(5) . . . . ?
C38 C39 C40 C31 -4.3(9) . . . . ?
C40 C31 C32 C33 172.3(5) . . . . ?
C40 C31 C32 C37 -3.3(8) . . . . ?
