# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I
_database_code_depnum_ccdc_archive 'CCDC 2350653'
loop_
_audit_author_name
_audit_author_address
'Takashi MINO'
;Chiba University
Japan
;
_audit_update_record             
;
2024-04-24 deposited with the CCDC.	2025-07-24 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H32 N O P'
_chemical_formula_iupac          ?
_chemical_formula_weight         477.55
_chemical_absolute_configuration unk

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.8268(8)
_cell_length_b                   16.7704(15)
_cell_length_c                   17.9763(17)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2661.0(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9982
_cell_measurement_theta_min      3.6044
_cell_measurement_theta_max      68.6768
_cell_measurement_temperature    173(2)

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.192
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1016

_exptl_absorpt_coefficient_mu    1.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_absorpt_correction_T_min  0.74
_exptl_absorpt_correction_T_max  0.81

_exptl_special_details           'SADABS (Sheldrick 1996)'

_diffrn_ambient_temperature      173(2)

_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_diffrn_source_type              ?

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'

_diffrn_measurement_device_type  'Bruker APEXII Ultra CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            13975
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_unetI/netI     0.0350
_diffrn_reflns_theta_min         3.604
_diffrn_reflns_theta_max         68.671
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20

_refine_special_details          
;
;

_reflns_number_total             4739
_reflns_number_gt                4686
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_gt          0.0902
_refine_ls_wR_factor_ref         0.0911
_refine_ls_goodness_of_fit_ref   0.736
_refine_ls_restrained_S_all      0.736
_refine_ls_number_reflns         4739
_refine_ls_number_parameters     320
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.5264P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.275
_refine_diff_density_min         -0.304
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack x determined using 1956 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.033(4)

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'
N N 0.0311 0.0180 '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'

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'

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_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P P1 0.52680(5) 0.49683(3) 0.71248(2) 0.02487(14) Uani d . . . 1 . .
O O1 0.7513(2) 0.48163(9) 0.94317(8) 0.0450(4) Uani d . . . 1 . .
N N1 0.76318(18) 0.53213(9) 0.82641(8) 0.0248(3) Uani d . . . 1 . .
C C1 0.4394(2) 0.49765(12) 0.61989(10) 0.0273(4) Uani d . . . 1 . .
C C20 0.7879(2) 0.47261(12) 0.87786(11) 0.0313(4) Uani d . . . 1 . .
C C13 0.8256(2) 0.53060(10) 0.75228(10) 0.0223(4) Uani d . . . 1 . .
C C6 0.3580(2) 0.43371(14) 0.59151(12) 0.0345(4) Uani d . . . 1 . .
H H6 0.357 0.3844 0.6176 0.041 Uiso calc U . R 1 . .
C C15 0.7848(2) 0.51923(11) 0.61953(10) 0.0285(4) Uani d . . . 1 . .
H H15 0.7192 0.5116 0.5783 0.034 Uiso calc U . R 1 . .
C C2 0.4367(2) 0.56947(13) 0.58027(12) 0.0349(4) Uani d . . . 1 . .
H H2 0.4902 0.6143 0.5991 0.042 Uiso calc U . R 1 . .
C C7 0.5411(2) 0.38994(12) 0.73318(11) 0.0324(4) Uani d . . . 1 . .
C C16 0.9385(2) 0.53215(13) 0.60811(11) 0.0329(4) Uani d . . . 1 . .
H H16 0.9779 0.5328 0.5589 0.04 Uiso calc U . R 1 . .
C C26 0.5479(3) 0.59972(14) 0.89577(12) 0.0372(5) Uani d . . . 1 . .
H H26A 0.4836 0.5573 0.8756 0.056 Uiso calc U . R 1 . .
H H26B 0.4912 0.6499 0.8965 0.056 Uiso calc U . R 1 . .
H H26C 0.5787 0.5859 0.9465 0.056 Uiso calc U . R 1 . .
C C14 0.7271(2) 0.51755(10) 0.69158(10) 0.0234(4) Uani d . . . 1 . .
C C27 0.8007(2) 0.67015(11) 0.87703(11) 0.0291(4) Uani d . . . 1 . .
C C17 1.0335(2) 0.54394(12) 0.66735(12) 0.0328(4) Uani d . . . 1 . .
H H17 1.1383 0.5524 0.6584 0.039 Uiso calc U . R 1 . .
C C18 0.9801(2) 0.54379(11) 0.74074(11) 0.0281(4) Uani d . . . 1 . .
C C25 0.6887(2) 0.60920(11) 0.84696(10) 0.0269(4) Uani d . . . 1 . .
H H25 0.651 0.6321 0.799 0.032 Uiso calc U . R 1 . .
C C21 0.8586(3) 0.39833(13) 0.85054(11) 0.0356(5) Uani d . . . 1 . .
H H21 0.9049 0.4 0.8029 0.043 Uiso calc U . R 1 . .
C C32 0.8696(3) 0.66247(13) 0.94624(13) 0.0410(5) Uani d . . . 1 . .
H H32 0.8461 0.6182 0.9771 0.049 Uiso calc U . R 1 . .
C C30 1.0076(3) 0.78455(15) 0.92623(15) 0.0464(6) Uani d . . . 1 . .
H H30 1.0788 0.8231 0.9429 0.056 Uiso calc U . R 1 . .
C C5 0.2779(3) 0.44110(16) 0.52540(13) 0.0421(5) Uani d . . . 1 . .
H H5 0.223 0.3967 0.5066 0.05 Uiso calc U . R 1 . .
C C3 0.3576(3) 0.57627(15) 0.51430(13) 0.0421(5) Uani d . . . 1 . .
H H3 0.3584 0.6252 0.4878 0.051 Uiso calc U . R 1 . .
C C8 0.6340(3) 0.33893(13) 0.69227(13) 0.0393(5) Uani d . . . 1 . .
H H8 0.6888 0.3593 0.651 0.047 Uiso calc U . R 1 . .
C C4 0.2771(2) 0.51191(17) 0.48680(12) 0.0423(5) Uani d . . . 1 . .
H H4 0.2218 0.5166 0.4417 0.051 Uiso calc U . R 1 . .
C C31 0.9727(3) 0.71939(15) 0.97040(14) 0.0474(6) Uani d . . . 1 . .
H H31 1.0197 0.7136 1.0176 0.057 Uiso calc U . R 1 . .
C C12 0.4627(3) 0.35923(15) 0.79351(13) 0.0446(5) Uani d . . . 1 . .
H H12 0.3988 0.3928 0.8222 0.053 Uiso calc U . R 1 . .
C C19 1.0902(2) 0.55630(16) 0.80380(13) 0.0429(5) Uani d . . . 1 . .
H H19A 1.1924 0.5635 0.7837 0.064 Uiso calc U . R 1 . .
H H19B 1.0886 0.5097 0.8367 0.064 Uiso calc U . R 1 . .
H H19C 1.061 0.6039 0.832 0.064 Uiso calc U . R 1 . .
C C22 0.8631(3) 0.32908(13) 0.88701(13) 0.0409(5) Uani d . . . 1 . .
C C28 0.8357(3) 0.73613(13) 0.83355(12) 0.0370(5) Uani d . . . 1 . .
H H28 0.7888 0.7424 0.7864 0.044 Uiso calc U . R 1 . .
C C10 0.5703(4) 0.22984(16) 0.77129(17) 0.0573(7) Uani d . . . 1 . .
H H10 0.5813 0.1754 0.7848 0.069 Uiso calc U . R 1 . .
C C29 0.9387(3) 0.79310(15) 0.85828(15) 0.0463(6) Uani d . . . 1 . .
H H29 0.9613 0.838 0.8281 0.056 Uiso calc U . R 1 . .
C C9 0.6476(3) 0.25948(14) 0.71074(17) 0.0509(6) Uani d . . . 1 . .
H H9 0.7101 0.2253 0.6818 0.061 Uiso calc U . R 1 . .
C C11 0.4780(4) 0.27840(18) 0.81201(17) 0.0593(7) Uani d . . . 1 . .
H H11 0.4237 0.2573 0.8532 0.071 Uiso calc U . R 1 . .
C C24 0.7880(5) 0.31204(16) 0.96002(15) 0.0615(8) Uani d . . . 1 . .
H H24A 0.7454 0.3615 0.9802 0.092 Uiso calc U . R 1 . .
H H24B 0.8628 0.2905 0.9949 0.092 Uiso calc U . R 1 . .
H H24C 0.7067 0.273 0.9527 0.092 Uiso calc U . R 1 . .
C C23 0.9456(5) 0.25925(16) 0.85447(17) 0.0641(8) Uani d . . . 1 . .
H H23A 0.9849 0.2736 0.8053 0.096 Uiso calc U . R 1 . .
H H23B 0.8759 0.2141 0.8497 0.096 Uiso calc U . R 1 . .
H H23C 1.0299 0.2445 0.8871 0.096 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 C1 . 1.8348(19) ?
P1 C7 . 1.835(2) ?
P1 C14 . 1.8408(18) ?
O1 C20 . 1.227(3) ?
N1 C20 . 1.378(3) ?
N1 C13 . 1.442(2) ?
N1 C25 . 1.497(2) ?
C1 C6 . 1.388(3) ?
C1 C2 . 1.399(3) ?
C20 C21 . 1.477(3) ?
C13 C18 . 1.397(3) ?
C13 C14 . 1.412(2) ?
C6 C5 . 1.388(3) ?
C6 H6 . 0.95 ?
C15 C16 . 1.388(3) ?
C15 C14 . 1.392(2) ?
C15 H15 . 0.95 ?
C2 C3 . 1.381(3) ?
C2 H2 . 0.95 ?
C7 C12 . 1.386(3) ?
C7 C8 . 1.395(3) ?
C16 C17 . 1.370(3) ?
C16 H16 . 0.95 ?
C26 C25 . 1.529(3) ?
C26 H26A . 0.98 ?
C26 H26B . 0.98 ?
C26 H26C . 0.98 ?
C27 C28 . 1.389(3) ?
C27 C32 . 1.391(3) ?
C27 C25 . 1.522(3) ?
C17 C18 . 1.401(3) ?
C17 H17 . 0.95 ?
C18 C19 . 1.507(3) ?
C25 H25 . 1.0 ?
C21 C22 . 1.334(3) ?
C21 H21 . 0.95 ?
C32 C31 . 1.388(4) ?
C32 H32 . 0.95 ?
C30 C29 . 1.372(4) ?
C30 C31 . 1.386(4) ?
C30 H30 . 0.95 ?
C5 C4 . 1.376(4) ?
C5 H5 . 0.95 ?
C3 C4 . 1.383(4) ?
C3 H3 . 0.95 ?
C8 C9 . 1.378(3) ?
C8 H8 . 0.95 ?
C4 H4 . 0.95 ?
C31 H31 . 0.95 ?
C12 C11 . 1.402(4) ?
C12 H12 . 0.95 ?
C19 H19A . 0.98 ?
C19 H19B . 0.98 ?
C19 H19C . 0.98 ?
C22 C23 . 1.498(4) ?
C22 C24 . 1.498(4) ?
C28 C29 . 1.391(3) ?
C28 H28 . 0.95 ?
C10 C11 . 1.365(5) ?
C10 C9 . 1.377(4) ?
C10 H10 . 0.95 ?
C29 H29 . 0.95 ?
C9 H9 . 0.95 ?
C11 H11 . 0.95 ?
C24 H24A . 0.98 ?
C24 H24B . 0.98 ?
C24 H24C . 0.98 ?
C23 H23A . 0.98 ?
C23 H23B . 0.98 ?
C23 H23C . 0.98 ?

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_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 P1 C7 . . 102.71(9) ?
C1 P1 C14 . . 102.56(8) ?
C7 P1 C14 . . 99.20(9) ?
C20 N1 C13 . . 123.15(15) ?
C20 N1 C25 . . 121.96(15) ?
C13 N1 C25 . . 114.29(14) ?
C6 C1 C2 . . 117.98(18) ?
C6 C1 P1 . . 123.05(16) ?
C2 C1 P1 . . 118.37(15) ?
O1 C20 N1 . . 120.75(18) ?
O1 C20 C21 . . 122.22(19) ?
N1 C20 C21 . . 117.03(17) ?
C18 C13 C14 . . 120.70(17) ?
C18 C13 N1 . . 120.48(16) ?
C14 C13 N1 . . 118.80(15) ?
C1 C6 C5 . . 120.6(2) ?
C1 C6 H6 . . 119.7 ?
C5 C6 H6 . . 119.7 ?
C16 C15 C14 . . 119.88(18) ?
C16 C15 H15 . . 120.1 ?
C14 C15 H15 . . 120.1 ?
C3 C2 C1 . . 121.1(2) ?
C3 C2 H2 . . 119.4 ?
C1 C2 H2 . . 119.4 ?
C12 C7 C8 . . 118.6(2) ?
C12 C7 P1 . . 119.17(18) ?
C8 C7 P1 . . 122.18(16) ?
C17 C16 C15 . . 120.37(19) ?
C17 C16 H16 . . 119.8 ?
C15 C16 H16 . . 119.8 ?
C25 C26 H26A . . 109.5 ?
C25 C26 H26B . . 109.5 ?
H26A C26 H26B . . 109.5 ?
C25 C26 H26C . . 109.5 ?
H26A C26 H26C . . 109.5 ?
H26B C26 H26C . . 109.5 ?
C15 C14 C13 . . 119.38(16) ?
C15 C14 P1 . . 123.04(14) ?
C13 C14 P1 . . 117.56(13) ?
C28 C27 C32 . . 118.67(19) ?
C28 C27 C25 . . 118.66(18) ?
C32 C27 C25 . . 122.66(19) ?
C16 C17 C18 . . 121.73(17) ?
C16 C17 H17 . . 119.1 ?
C18 C17 H17 . . 119.1 ?
C13 C18 C17 . . 117.94(17) ?
C13 C18 C19 . . 122.63(18) ?
C17 C18 C19 . . 119.42(18) ?
N1 C25 C27 . . 112.48(15) ?
N1 C25 C26 . . 114.14(16) ?
C27 C25 C26 . . 113.21(16) ?
N1 C25 H25 . . 105.3 ?
C27 C25 H25 . . 105.3 ?
C26 C25 H25 . . 105.3 ?
C22 C21 C20 . . 125.7(2) ?
C22 C21 H21 . . 117.2 ?
C20 C21 H21 . . 117.2 ?
C31 C32 C27 . . 120.2(2) ?
C31 C32 H32 . . 119.9 ?
C27 C32 H32 . . 119.9 ?
C29 C30 C31 . . 119.6(2) ?
C29 C30 H30 . . 120.2 ?
C31 C30 H30 . . 120.2 ?
C4 C5 C6 . . 120.8(2) ?
C4 C5 H5 . . 119.6 ?
C6 C5 H5 . . 119.6 ?
C2 C3 C4 . . 120.1(2) ?
C2 C3 H3 . . 119.9 ?
C4 C3 H3 . . 119.9 ?
C9 C8 C7 . . 121.2(2) ?
C9 C8 H8 . . 119.4 ?
C7 C8 H8 . . 119.4 ?
C5 C4 C3 . . 119.4(2) ?
C5 C4 H4 . . 120.3 ?
C3 C4 H4 . . 120.3 ?
C30 C31 C32 . . 120.6(2) ?
C30 C31 H31 . . 119.7 ?
C32 C31 H31 . . 119.7 ?
C7 C12 C11 . . 119.8(3) ?
C7 C12 H12 . . 120.1 ?
C11 C12 H12 . . 120.1 ?
C18 C19 H19A . . 109.5 ?
C18 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C18 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C21 C22 C23 . . 120.2(2) ?
C21 C22 C24 . . 125.7(2) ?
C23 C22 C24 . . 114.1(2) ?
C27 C28 C29 . . 120.8(2) ?
C27 C28 H28 . . 119.6 ?
C29 C28 H28 . . 119.6 ?
C11 C10 C9 . . 120.3(2) ?
C11 C10 H10 . . 119.9 ?
C9 C10 H10 . . 119.9 ?
C30 C29 C28 . . 120.2(2) ?
C30 C29 H29 . . 119.9 ?
C28 C29 H29 . . 119.9 ?
C10 C9 C8 . . 119.7(3) ?
C10 C9 H9 . . 120.1 ?
C8 C9 H9 . . 120.1 ?
C10 C11 C12 . . 120.5(3) ?
C10 C11 H11 . . 119.8 ?
C12 C11 H11 . . 119.8 ?
C22 C24 H24A . . 109.5 ?
C22 C24 H24B . . 109.5 ?
H24A C24 H24B . . 109.5 ?
C22 C24 H24C . . 109.5 ?
H24A C24 H24C . . 109.5 ?
H24B C24 H24C . . 109.5 ?
C22 C23 H23A . . 109.5 ?
C22 C23 H23B . . 109.5 ?
H23A C23 H23B . . 109.5 ?
C22 C23 H23C . . 109.5 ?
H23A C23 H23C . . 109.5 ?
H23B C23 H23C . . 109.5 ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 P1 C1 C6 . . . . 20.73(18) ?
C14 P1 C1 C6 . . . . 123.33(16) ?
C7 P1 C1 C2 . . . . -168.30(15) ?
C14 P1 C1 C2 . . . . -65.70(16) ?
C13 N1 C20 O1 . . . . 169.42(19) ?
C25 N1 C20 O1 . . . . -1.2(3) ?
C13 N1 C20 C21 . . . . -11.0(3) ?
C25 N1 C20 C21 . . . . 178.37(17) ?
C20 N1 C13 C18 . . . . -72.5(2) ?
C25 N1 C13 C18 . . . . 98.80(19) ?
C20 N1 C13 C14 . . . . 109.1(2) ?
C25 N1 C13 C14 . . . . -79.6(2) ?
C2 C1 C6 C5 . . . . 0.6(3) ?
P1 C1 C6 C5 . . . . 171.65(16) ?
C6 C1 C2 C3 . . . . -1.1(3) ?
P1 C1 C2 C3 . . . . -172.49(16) ?
C1 P1 C7 C12 . . . . -117.67(18) ?
C14 P1 C7 C12 . . . . 137.12(17) ?
C1 P1 C7 C8 . . . . 65.40(19) ?
C14 P1 C7 C8 . . . . -39.81(19) ?
C14 C15 C16 C17 . . . . -0.6(3) ?
C16 C15 C14 C13 . . . . 1.2(3) ?
C16 C15 C14 P1 . . . . -177.45(15) ?
C18 C13 C14 C15 . . . . -1.1(3) ?
N1 C13 C14 C15 . . . . 177.34(16) ?
C18 C13 C14 P1 . . . . 177.67(14) ?
N1 C13 C14 P1 . . . . -3.9(2) ?
C1 P1 C14 C15 . . . . -8.66(17) ?
C7 P1 C14 C15 . . . . 96.68(16) ?
C1 P1 C14 C13 . . . . 172.64(14) ?
C7 P1 C14 C13 . . . . -82.02(15) ?
C15 C16 C17 C18 . . . . -0.3(3) ?
C14 C13 C18 C17 . . . . 0.3(3) ?
N1 C13 C18 C17 . . . . -178.14(16) ?
C14 C13 C18 C19 . . . . -178.70(18) ?
N1 C13 C18 C19 . . . . 2.9(3) ?
C16 C17 C18 C13 . . . . 0.4(3) ?
C16 C17 C18 C19 . . . . 179.4(2) ?
C20 N1 C25 C27 . . . . 85.8(2) ?
C13 N1 C25 C27 . . . . -85.55(19) ?
C20 N1 C25 C26 . . . . -44.9(2) ?
C13 N1 C25 C26 . . . . 143.70(17) ?
C28 C27 C25 N1 . . . . 109.3(2) ?
C32 C27 C25 N1 . . . . -70.7(2) ?
C28 C27 C25 C26 . . . . -119.5(2) ?
C32 C27 C25 C26 . . . . 60.6(3) ?
O1 C20 C21 C22 . . . . 14.3(4) ?
N1 C20 C21 C22 . . . . -165.3(2) ?
C28 C27 C32 C31 . . . . -0.9(3) ?
C25 C27 C32 C31 . . . . 179.1(2) ?
C1 C6 C5 C4 . . . . -0.2(3) ?
C1 C2 C3 C4 . . . . 1.0(3) ?
C12 C7 C8 C9 . . . . 0.4(3) ?
P1 C7 C8 C9 . . . . 177.31(19) ?
C6 C5 C4 C3 . . . . 0.2(3) ?
C2 C3 C4 C5 . . . . -0.6(3) ?
C29 C30 C31 C32 . . . . 0.5(4) ?
C27 C32 C31 C30 . . . . 0.3(4) ?
C8 C7 C12 C11 . . . . -0.1(3) ?
P1 C7 C12 C11 . . . . -177.1(2) ?
C20 C21 C22 C23 . . . . -176.9(2) ?
C20 C21 C22 C24 . . . . 4.6(4) ?
C32 C27 C28 C29 . . . . 0.6(3) ?
C25 C27 C28 C29 . . . . -179.3(2) ?
C31 C30 C29 C28 . . . . -0.8(4) ?
C27 C28 C29 C30 . . . . 0.2(4) ?
C11 C10 C9 C8 . . . . 1.4(4) ?
C7 C8 C9 C10 . . . . -1.0(4) ?
C9 C10 C11 C12 . . . . -1.1(4) ?
C7 C12 C11 C10 . . . . 0.4(4) ?


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2474633'
loop_
_audit_author_name
_audit_author_address
'Takashi MINO'
;Chiba University
Japan
;
_audit_update_record             
;
2025-07-21 deposited with the CCDC.	2025-07-24 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H30 N O P'
_chemical_formula_iupac          ?
_chemical_formula_weight         463.53
_chemical_absolute_configuration rmad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.4029(3)
_cell_length_b                   11.7508(5)
_cell_length_c                   28.6448(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2491.81(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9933
_cell_measurement_theta_min      4.0663
_cell_measurement_theta_max      66.6960
_cell_measurement_temperature    173(2)

_exptl_crystal_description       Plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984

_exptl_absorpt_coefficient_mu    1.150
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_absorpt_correction_T_min  0.86
_exptl_absorpt_correction_T_max  0.94

_exptl_special_details           'SADABS (Sheldrick 1996)'

_diffrn_ambient_temperature      173(2)

_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_diffrn_source_type              ?

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'

_diffrn_measurement_device_type  'Bruker APEXII Ultra CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            35514
_diffrn_reflns_av_R_equivalents  0.0221
_diffrn_reflns_av_unetI/netI     0.0170
_diffrn_reflns_theta_min         3.085
_diffrn_reflns_theta_max         66.691
_diffrn_reflns_theta_full        66.691
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_limit_l_max       34

_refine_special_details          
;
;

_reflns_number_total             4403
_reflns_number_gt                4385
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0310
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_gt          0.0915
_refine_ls_wR_factor_ref         0.0916
_refine_ls_goodness_of_fit_ref   0.783
_refine_ls_restrained_S_all      0.783
_refine_ls_number_reflns         4403
_refine_ls_number_parameters     310
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.3552P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.388
_refine_diff_density_min         -0.161
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 926 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.033(2)

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'
N N 0.0311 0.0180 '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'

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'

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_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P P1 0.48223(7) 0.47631(4) 0.37819(2) 0.03385(15) Uani d . . . 1 . .
O O1 0.3531(2) 0.29760(15) 0.24887(5) 0.0470(4) Uani d . . . 1 . .
N N1 0.3698(2) 0.25732(13) 0.32591(5) 0.0300(3) Uani d . . . 1 . .
C C13 0.2996(2) 0.26534(15) 0.37278(6) 0.0271(4) Uani d . . . 1 . .
C C26 0.5730(2) 0.09364(17) 0.35110(6) 0.0304(4) Uani d . . . 1 . .
C C18 0.1852(2) 0.17846(16) 0.38881(6) 0.0304(4) Uani d . . . 1 . .
C C24 0.5323(3) 0.18531(17) 0.31561(6) 0.0343(4) Uani d . . . 1 . .
H H24 0.507609 0.145669 0.285382 0.041 Uiso calc U . R 1 . .
C C17 0.1264(3) 0.18285(16) 0.43496(7) 0.0333(4) Uani d . . . 1 . .
H H17 0.049619 0.124426 0.44644 0.04 Uiso calc U . R 1 . .
C C15 0.2855(3) 0.35680(17) 0.44774(6) 0.0342(4) Uani d . . . 1 . .
H H15 0.318972 0.417228 0.468011 0.041 Uiso calc U . R 1 . .
C C20 0.2906(3) 0.30916(17) 0.28831(6) 0.0344(4) Uani d . . . 1 . .
C C7 0.5815(3) 0.53120(16) 0.43264(7) 0.0344(4) Uani d . . . 1 . .
C C14 0.3465(3) 0.35702(15) 0.40183(6) 0.0280(4) Uani d . . . 1 . .
C C31 0.6308(3) 0.11835(17) 0.39635(7) 0.0360(4) Uani d . . . 1 . .
H H31 0.634543 0.195181 0.406621 0.043 Uiso calc U . R 1 . .
C C21 0.1281(3) 0.37989(18) 0.29713(7) 0.0368(4) Uani d . . . 1 . .
H H21 0.07245 0.377292 0.326991 0.044 Uiso calc U . R 1 . .
C C1 0.3079(3) 0.58291(16) 0.36618(6) 0.0337(4) Uani d . . . 1 . .
C C2 0.3481(3) 0.66272(18) 0.33128(7) 0.0419(5) Uani d . . . 1 . .
H H2 0.458514 0.657557 0.314537 0.05 Uiso calc U . R 1 . .
C C8 0.5181(3) 0.62484(18) 0.45739(8) 0.0438(5) Uani d . . . 1 . .
H H8 0.416282 0.665749 0.44617 0.053 Uiso calc U . R 1 . .
C C16 0.1771(3) 0.27006(17) 0.46435(7) 0.0369(4) Uani d . . . 1 . .
H H16 0.137603 0.270541 0.495904 0.044 Uiso calc U . R 1 . .
C C6 0.1436(3) 0.59157(17) 0.38911(7) 0.0401(5) Uani d . . . 1 . .
H H6 0.113224 0.537224 0.412378 0.048 Uiso calc U . R 1 . .
C C30 0.6827(3) 0.0325(2) 0.42635(7) 0.0435(5) Uani d . . . 1 . .
H H30 0.720316 0.050668 0.457163 0.052 Uiso calc U . R 1 . .
C C12 0.7353(3) 0.47583(18) 0.44905(8) 0.0435(5) Uani d . . . 1 . .
H H12 0.783525 0.413589 0.431951 0.052 Uiso calc U . R 1 . .
C C27 0.5732(3) -0.01954(18) 0.33739(8) 0.0407(5) Uani d . . . 1 . .
H H27 0.535553 -0.03835 0.306639 0.049 Uiso calc U . R 1 . .
C C19 0.1244(3) 0.08224(18) 0.35792(7) 0.0405(5) Uani d . . . 1 . .
H H19A 0.212273 0.020013 0.359582 0.061 Uiso calc U . R 1 . .
H H19B 0.115114 0.109175 0.325627 0.061 Uiso calc U . R 1 . .
H H19C 0.006111 0.054862 0.36842 0.061 Uiso calc U . R 1 . .
C C5 0.0230(3) 0.6779(2) 0.37875(8) 0.0495(5) Uani d . . . 1 . .
H H5 -0.088164 0.682747 0.395195 0.059 Uiso calc U . R 1 . .
C C10 0.7517(4) 0.6010(2) 0.51486(9) 0.0510(6) Uani d . . . 1 . .
H H10 0.807779 0.623425 0.543229 0.061 Uiso calc U . R 1 . .
C C9 0.6025(4) 0.6591(2) 0.49842(9) 0.0509(6) Uani d . . . 1 . .
H H9 0.557431 0.722809 0.515204 0.061 Uiso calc U . R 1 . .
C C29 0.6804(3) -0.0793(2) 0.41200(9) 0.0479(5) Uani d . . . 1 . .
H H29 0.715706 -0.138244 0.432799 0.058 Uiso calc U . R 1 . .
C C22 0.0590(3) 0.44630(19) 0.26459(7) 0.0413(5) Uani d . . . 1 . .
H H22 0.115571 0.445773 0.23482 0.05 Uiso calc U . R 1 . .
C C11 0.8185(3) 0.5101(2) 0.48981(10) 0.0530(6) Uani d . . . 1 . .
H H11 0.922477 0.470841 0.500671 0.064 Uiso calc U . R 1 . .
C C4 0.0632(4) 0.7569(2) 0.34470(9) 0.0563(6) Uani d . . . 1 . .
H H4 -0.020094 0.815848 0.337451 0.068 Uiso calc U . R 1 . .
C C25 0.6996(3) 0.2592(2) 0.30787(9) 0.0510(6) Uani d . . . 1 . .
H H25A 0.671203 0.319681 0.285498 0.077 Uiso calc U . R 1 . .
H H25B 0.797873 0.212079 0.295556 0.077 Uiso calc U . R 1 . .
H H25C 0.73685 0.293106 0.3376 0.077 Uiso calc U . R 1 . .
C C28 0.6261(3) -0.10513(19) 0.36694(10) 0.0513(6) Uani d . . . 1 . .
H H28 0.625488 -0.181888 0.356531 0.062 Uiso calc U . R 1 . .
C C23 -0.1006(3) 0.5221(2) 0.27072(8) 0.0480(5) Uani d . . . 1 . .
H H23A -0.15058 0.511734 0.302119 0.072 Uiso calc U . R 1 . .
H H23B -0.19273 0.502783 0.247447 0.072 Uiso calc U . R 1 . .
H H23C -0.063633 0.601513 0.266624 0.072 Uiso calc U . R 1 . .
C C3 0.2263(4) 0.7494(2) 0.32118(9) 0.0553(6) Uani d . . . 1 . .
H H3 0.255233 0.804064 0.297916 0.066 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
P1 C1 . 1.831(2) ?
P1 C7 . 1.841(2) ?
P1 C14 . 1.8527(18) ?
O1 C20 . 1.229(2) ?
N1 C20 . 1.369(3) ?
N1 C13 . 1.443(2) ?
N1 C24 . 1.500(2) ?
C13 C18 . 1.404(3) ?
C13 C14 . 1.405(3) ?
C26 C27 . 1.387(3) ?
C26 C31 . 1.396(3) ?
C26 C24 . 1.511(3) ?
C18 C17 . 1.393(3) ?
C18 C19 . 1.505(3) ?
C24 C25 . 1.528(3) ?
C17 C16 . 1.378(3) ?
C15 C16 . 1.382(3) ?
C15 C14 . 1.391(3) ?
C20 C21 . 1.483(3) ?
C7 C8 . 1.390(3) ?
C7 C12 . 1.393(3) ?
C31 C30 . 1.380(3) ?
C21 C22 . 1.319(3) ?
C1 C6 . 1.386(3) ?
C1 C2 . 1.403(3) ?
C2 C3 . 1.391(4) ?
C8 C9 . 1.391(3) ?
C6 C5 . 1.383(3) ?
C30 C29 . 1.377(4) ?
C12 C11 . 1.380(3) ?
C27 C28 . 1.371(3) ?
C5 C4 . 1.379(4) ?
C10 C11 . 1.378(4) ?
C10 C9 . 1.381(4) ?
C29 C28 . 1.386(4) ?
C22 C23 . 1.490(3) ?
C4 C3 . 1.385(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_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 P1 C7 . . 101.58(9) ?
C1 P1 C14 . . 101.77(9) ?
C7 P1 C14 . . 99.90(8) ?
C20 N1 C13 . . 123.27(15) ?
C20 N1 C24 . . 116.09(15) ?
C13 N1 C24 . . 120.58(14) ?
C18 C13 C14 . . 120.87(16) ?
C18 C13 N1 . . 118.31(16) ?
C14 C13 N1 . . 120.81(16) ?
C27 C26 C31 . . 117.52(19) ?
C27 C26 C24 . . 119.56(17) ?
C31 C26 C24 . . 122.52(17) ?
C17 C18 C13 . . 118.17(17) ?
C17 C18 C19 . . 119.51(17) ?
C13 C18 C19 . . 122.31(16) ?
N1 C24 C26 . . 115.44(14) ?
N1 C24 C25 . . 110.97(16) ?
C26 C24 C25 . . 109.92(18) ?
C16 C17 C18 . . 121.48(17) ?
C16 C15 C14 . . 121.03(17) ?
O1 C20 N1 . . 120.83(19) ?
O1 C20 C21 . . 121.61(18) ?
N1 C20 C21 . . 117.55(16) ?
C8 C7 C12 . . 118.25(19) ?
C8 C7 P1 . . 125.07(16) ?
C12 C7 P1 . . 116.64(16) ?
C15 C14 C13 . . 118.59(16) ?
C15 C14 P1 . . 121.54(14) ?
C13 C14 P1 . . 119.86(13) ?
C30 C31 C26 . . 120.77(19) ?
C22 C21 C20 . . 121.71(19) ?
C6 C1 C2 . . 118.3(2) ?
C6 C1 P1 . . 125.43(15) ?
C2 C1 P1 . . 116.22(17) ?
C3 C2 C1 . . 120.0(2) ?
C7 C8 C9 . . 120.6(2) ?
C17 C16 C15 . . 119.76(17) ?
C5 C6 C1 . . 121.22(19) ?
C29 C30 C31 . . 120.6(2) ?
C11 C12 C7 . . 120.9(2) ?
C28 C27 C26 . . 121.9(2) ?
C4 C5 C6 . . 120.4(2) ?
C11 C10 C9 . . 119.5(2) ?
C10 C9 C8 . . 120.3(2) ?
C30 C29 C28 . . 119.4(2) ?
C21 C22 C23 . . 125.3(2) ?
C10 C11 C12 . . 120.4(2) ?
C5 C4 C3 . . 119.3(2) ?
C27 C28 C29 . . 119.8(2) ?
C4 C3 C2 . . 120.7(2) ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C20 N1 C13 C18 . . . . 94.8(2) ?
C24 N1 C13 C18 . . . . -82.2(2) ?
C20 N1 C13 C14 . . . . -86.0(2) ?
C24 N1 C13 C14 . . . . 97.0(2) ?
C14 C13 C18 C17 . . . . -3.0(3) ?
N1 C13 C18 C17 . . . . 176.20(16) ?
C14 C13 C18 C19 . . . . 176.75(17) ?
N1 C13 C18 C19 . . . . -4.1(3) ?
C20 N1 C24 C26 . . . . -156.28(17) ?
C13 N1 C24 C26 . . . . 20.9(2) ?
C20 N1 C24 C25 . . . . 77.8(2) ?
C13 N1 C24 C25 . . . . -105.0(2) ?
C27 C26 C24 N1 . . . . 119.4(2) ?
C31 C26 C24 N1 . . . . -68.0(2) ?
C27 C26 C24 C25 . . . . -114.2(2) ?
C31 C26 C24 C25 . . . . 58.4(2) ?
C13 C18 C17 C16 . . . . 0.5(3) ?
C19 C18 C17 C16 . . . . -179.28(19) ?
C13 N1 C20 O1 . . . . -178.27(18) ?
C24 N1 C20 O1 . . . . -1.2(3) ?
C13 N1 C20 C21 . . . . 2.1(3) ?
C24 N1 C20 C21 . . . . 179.24(16) ?
C1 P1 C7 C8 . . . . 4.98(19) ?
C14 P1 C7 C8 . . . . -99.33(18) ?
C1 P1 C7 C12 . . . . -172.91(15) ?
C14 P1 C7 C12 . . . . 82.78(16) ?
C16 C15 C14 C13 . . . . -1.7(3) ?
C16 C15 C14 P1 . . . . 176.83(16) ?
C18 C13 C14 C15 . . . . 3.6(3) ?
N1 C13 C14 C15 . . . . -175.57(17) ?
C18 C13 C14 P1 . . . . -174.95(14) ?
N1 C13 C14 P1 . . . . 5.9(2) ?
C1 P1 C14 C15 . . . . -79.19(17) ?
C7 P1 C14 C15 . . . . 24.97(18) ?
C1 P1 C14 C13 . . . . 99.32(15) ?
C7 P1 C14 C13 . . . . -156.52(15) ?
C27 C26 C31 C30 . . . . -1.2(3) ?
C24 C26 C31 C30 . . . . -173.93(18) ?
O1 C20 C21 C22 . . . . -9.9(3) ?
N1 C20 C21 C22 . . . . 169.7(2) ?
C7 P1 C1 C6 . . . . -75.97(19) ?
C14 P1 C1 C6 . . . . 26.85(19) ?
C7 P1 C1 C2 . . . . 102.90(15) ?
C14 P1 C1 C2 . . . . -154.28(15) ?
C6 C1 C2 C3 . . . . 1.5(3) ?
P1 C1 C2 C3 . . . . -177.46(16) ?
C12 C7 C8 C9 . . . . -2.5(3) ?
P1 C7 C8 C9 . . . . 179.67(18) ?
C18 C17 C16 C15 . . . . 1.4(3) ?
C14 C15 C16 C17 . . . . -0.8(3) ?
C2 C1 C6 C5 . . . . -1.3(3) ?
P1 C1 C6 C5 . . . . 177.53(17) ?
C26 C31 C30 C29 . . . . 0.8(3) ?
C8 C7 C12 C11 . . . . 2.5(3) ?
P1 C7 C12 C11 . . . . -179.42(17) ?
C31 C26 C27 C28 . . . . 0.7(3) ?
C24 C26 C27 C28 . . . . 173.6(2) ?
C1 C6 C5 C4 . . . . 0.8(4) ?
C11 C10 C9 C8 . . . . 1.3(4) ?
C7 C8 C9 C10 . . . . 0.6(4) ?
C31 C30 C29 C28 . . . . 0.3(3) ?
C20 C21 C22 C23 . . . . -178.4(2) ?
C9 C10 C11 C12 . . . . -1.3(4) ?
C7 C12 C11 C10 . . . . -0.7(3) ?
C6 C5 C4 C3 . . . . -0.5(4) ?
C26 C27 C28 C29 . . . . 0.4(3) ?
C30 C29 C28 C27 . . . . -0.8(4) ?
C5 C4 C3 C2 . . . . 0.6(4) ?
C1 C2 C3 C4 . . . . -1.2(3) ?


####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_I_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2474632'
loop_
_audit_author_name
_audit_author_address
'Takashi MINO'
;Chiba University
Japan
;
_audit_update_record             
;
2025-07-21 deposited with the CCDC.	2025-07-24 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C31 H30 N O P'
_chemical_formula_iupac          ?
_chemical_formula_weight         463.53
_chemical_absolute_configuration rmad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   8.3172(2)
_cell_length_b                   11.7149(3)
_cell_length_c                   26.1750(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2550.37(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9995
_cell_measurement_theta_min      5.0669
_cell_measurement_theta_max      66.6096
_cell_measurement_temperature    173(2)

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.400
_exptl_crystal_density_diffrn    1.207
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             984

_exptl_absorpt_coefficient_mu    1.124
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_absorpt_correction_T_min  0.54
_exptl_absorpt_correction_T_max  0.66

_exptl_special_details           'SADABS (Sheldrick 1996)'

_diffrn_ambient_temperature      173(2)

_diffrn_source                   'Bruker TXS fine-focus rotating anode'
_diffrn_source_type              ?

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Bruker Helios multilayer confocal mirror'

_diffrn_measurement_device_type  'Bruker APEXII Ultra CCD area detector'
_diffrn_measurement_method       'Phi and Omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            50219
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_unetI/netI     0.0156
_diffrn_reflns_theta_min         3.377
_diffrn_reflns_theta_max         66.613
_diffrn_reflns_theta_full        66.613
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31

_refine_special_details          
;
;

_reflns_number_total             4428
_reflns_number_gt                4421
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0280
_refine_ls_R_factor_gt           0.0280
_refine_ls_wR_factor_gt          0.0832
_refine_ls_wR_factor_ref         0.0832
_refine_ls_goodness_of_fit_ref   0.691
_refine_ls_restrained_S_all      0.691
_refine_ls_number_reflns         4428
_refine_ls_number_parameters     310
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²+0.5857P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.352
_refine_diff_density_min         -0.257
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 926 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.037(2)

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'
N N 0.0311 0.0180 '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'

_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'

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_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.4998(2) 0.51057(15) 0.31093(6) 0.0248(3) Uani d . . . 1 . .
C C2 0.5838(2) 0.44331(15) 0.34617(6) 0.0252(3) Uani d . . . 1 . .
C C3 0.7077(2) 0.37375(16) 0.32878(7) 0.0296(4) Uani d . . . 1 . .
H H3 0.764985 0.327056 0.352209 0.036 Uiso calc U . R 1 . .
C C4 0.7480(2) 0.37226(16) 0.27738(8) 0.0324(4) Uani d . . . 1 . .
H H4 0.833389 0.325007 0.265801 0.039 Uiso calc U . R 1 . .
C C5 0.6651(2) 0.43875(17) 0.24314(7) 0.0315(4) Uani d . . . 1 . .
H H5 0.69346 0.435997 0.208005 0.038 Uiso calc U . R 1 . .
C C6 0.5401(2) 0.51038(16) 0.25876(7) 0.0285(4) Uani d . . . 1 . .
C C7 0.4555(3) 0.5852(2) 0.22081(7) 0.0404(5) Uani d . . . 1 . .
H H7A 0.340845 0.566092 0.22022 0.061 Uiso calc U . R 1 . .
H H7B 0.50165 0.573055 0.18679 0.061 Uiso calc U . R 1 . .
H H7C 0.468875 0.665378 0.230634 0.061 Uiso calc U . R 1 . .
C C8 0.2048(2) 0.54352(17) 0.33670(7) 0.0305(4) Uani d . . . 1 . .
H H8 0.171307 0.571105 0.371249 0.037 Uiso calc U . R 1 . .
C C9 0.0892(3) 0.5982(2) 0.29804(9) 0.0445(5) Uani d . . . 1 . .
H H9A 0.10474 0.68116 0.297919 0.067 Uiso calc U . R 1 . .
H H9B -0.021914 0.580658 0.307675 0.067 Uiso calc U . R 1 . .
H H9C 0.111077 0.567792 0.263867 0.067 Uiso calc U . R 1 . .
C C10 0.1833(2) 0.41473(17) 0.33681(7) 0.0314(4) Uani d . . . 1 . .
C C11 0.2098(3) 0.3473(2) 0.29374(8) 0.0394(5) Uani d . . . 1 . .
H H11 0.253995 0.380651 0.263785 0.047 Uiso calc U . R 1 . .
C C12 0.1722(3) 0.2325(2) 0.29430(10) 0.0487(6) Uani d . . . 1 . .
H H12 0.192562 0.187229 0.264877 0.058 Uiso calc U . R 1 . .
C C13 0.1054(3) 0.1827(2) 0.33709(11) 0.0526(6) Uani d . . . 1 . .
H H13 0.078291 0.103905 0.336977 0.063 Uiso calc U . R 1 . .
C C14 0.0784(3) 0.2481(2) 0.38004(10) 0.0486(6) Uani d . . . 1 . .
H H14 0.032677 0.214324 0.409676 0.058 Uiso calc U . R 1 . .
C C15 0.1180(3) 0.36358(19) 0.38000(8) 0.0377(5) Uani d . . . 1 . .
H H15 0.100194 0.407943 0.40985 0.045 Uiso calc U . R 1 . .
C C16 0.5807(2) 0.30161(16) 0.43328(6) 0.0286(4) Uani d . . . 1 . .
C C17 0.7010(3) 0.27680(18) 0.46802(8) 0.0395(5) Uani d . . . 1 . .
H H17 0.766361 0.336374 0.481273 0.047 Uiso calc U . R 1 . .
C C18 0.7265(3) 0.1650(2) 0.48353(9) 0.0494(6) Uani d . . . 1 . .
H H18 0.809661 0.148947 0.507344 0.059 Uiso calc U . R 1 . .
C C19 0.6341(3) 0.07746(18) 0.46518(9) 0.0453(5) Uani d . . . 1 . .
H H19 0.65281 0.001352 0.476202 0.054 Uiso calc U . R 1 . .
C C20 0.5130(3) 0.10085(18) 0.43038(8) 0.0422(5) Uani d . . . 1 . .
H H20 0.448136 0.04079 0.417335 0.051 Uiso calc U . R 1 . .
C C21 0.4870(3) 0.21217(17) 0.41471(8) 0.0370(4) Uani d . . . 1 . .
H H21 0.403759 0.227877 0.390864 0.044 Uiso calc U . R 1 . .
C C22 0.6704(2) 0.53532(15) 0.44571(7) 0.0305(4) Uani d . . . 1 . .
C C23 0.8129(3) 0.57368(18) 0.42474(8) 0.0374(5) Uani d . . . 1 . .
H H23 0.841085 0.551831 0.390956 0.045 Uiso calc U . R 1 . .
C C24 0.9157(3) 0.64391(19) 0.45249(9) 0.0466(5) Uani d . . . 1 . .
H H24 1.012399 0.671134 0.437478 0.056 Uiso calc U . R 1 . .
C C25 0.8763(3) 0.67392(19) 0.50214(9) 0.0487(6) Uani d . . . 1 . .
H H25 0.946206 0.721998 0.521147 0.058 Uiso calc U . R 1 . .
C C26 0.7368(3) 0.6345(2) 0.52407(8) 0.0475(6) Uani d . . . 1 . .
H H26 0.711597 0.653732 0.558411 0.057 Uiso calc U . R 1 . .
C C27 0.6328(3) 0.56672(18) 0.49588(8) 0.0397(5) Uani d . . . 1 . .
H H27 0.535008 0.541314 0.510795 0.048 Uiso calc U . R 1 . .
C C28 0.4068(3) 0.69313(16) 0.34520(7) 0.0329(4) Uani d . . . 1 . .
C C29 0.5748(3) 0.73340(18) 0.33992(8) 0.0383(5) Uani d . . . 1 . .
H H29 0.64727 0.691168 0.31919 0.046 Uiso calc U . R 1 . .
C C30 0.6265(3) 0.8261(2) 0.36315(9) 0.0484(6) Uani d . . . 1 . .
H H30 0.549729 0.868589 0.382135 0.058 Uiso calc U . R 1 . .
C C31 0.7935(4) 0.8701(2) 0.36236(12) 0.0621(7) Uani d . . . 1 . .
H H31A 0.856953 0.826813 0.337472 0.093 Uiso calc U . R 1 . .
H H31B 0.841391 0.861779 0.396368 0.093 Uiso calc U . R 1 . .
H H31C 0.792682 0.950981 0.352726 0.093 Uiso calc U . R 1 . .
N N1 0.3728(2) 0.58481(13) 0.32850(6) 0.0284(3) Uani d . . . 1 . .
O O1 0.3009(2) 0.75366(13) 0.36393(6) 0.0458(4) Uani d . . . 1 . .
P P1 0.52046(6) 0.44583(4) 0.41369(2) 0.02692(14) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.400(3) ?
C1 C6 . 1.406(2) ?
C1 N1 . 1.443(2) ?
C2 C3 . 1.391(3) ?
C2 P1 . 1.8443(17) ?
C3 C4 . 1.387(3) ?
C4 C5 . 1.373(3) ?
C5 C6 . 1.397(3) ?
C6 C7 . 1.500(3) ?
C8 N1 . 1.494(3) ?
C8 C10 . 1.519(3) ?
C8 C9 . 1.536(3) ?
C10 C15 . 1.390(3) ?
C10 C11 . 1.394(3) ?
C11 C12 . 1.382(4) ?
C12 C13 . 1.380(4) ?
C13 C14 . 1.379(4) ?
C14 C15 . 1.393(3) ?
C16 C17 . 1.383(3) ?
C16 C21 . 1.393(3) ?
C16 P1 . 1.8352(18) ?
C17 C18 . 1.387(3) ?
C18 C19 . 1.369(3) ?
C19 C20 . 1.385(3) ?
C20 C21 . 1.384(3) ?
C22 C23 . 1.381(3) ?
C22 C27 . 1.399(3) ?
C22 P1 . 1.832(2) ?
C23 C24 . 1.391(3) ?
C24 C25 . 1.386(4) ?
C25 C26 . 1.375(4) ?
C26 C27 . 1.387(3) ?
C28 O1 . 1.233(3) ?
C28 N1 . 1.372(3) ?
C28 C29 . 1.481(3) ?
C29 C30 . 1.317(3) ?
C30 C31 . 1.482(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_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 121.35(17) ?
C2 C1 N1 . . 119.62(14) ?
C6 C1 N1 . . 118.99(16) ?
C3 C2 C1 . . 118.94(16) ?
C3 C2 P1 . . 122.33(14) ?
C1 C2 P1 . . 118.69(13) ?
C4 C3 C2 . . 120.29(18) ?
C5 C4 C3 . . 120.31(18) ?
C4 C5 C6 . . 121.57(17) ?
C5 C6 C1 . . 117.53(17) ?
C5 C6 C7 . . 120.42(17) ?
C1 C6 C7 . . 122.04(18) ?
N1 C8 C10 . . 115.61(15) ?
N1 C8 C9 . . 110.84(16) ?
C10 C8 C9 . . 109.98(18) ?
C15 C10 C11 . . 118.4(2) ?
C15 C10 C8 . . 118.41(18) ?
C11 C10 C8 . . 122.84(19) ?
C12 C11 C10 . . 120.5(2) ?
C13 C12 C11 . . 120.7(2) ?
C14 C13 C12 . . 119.5(2) ?
C13 C14 C15 . . 120.0(2) ?
C10 C15 C14 . . 120.8(2) ?
C17 C16 C21 . . 118.43(18) ?
C17 C16 P1 . . 125.08(15) ?
C21 C16 P1 . . 116.24(14) ?
C16 C17 C18 . . 120.1(2) ?
C19 C18 C17 . . 121.3(2) ?
C18 C19 C20 . . 119.4(2) ?
C21 C20 C19 . . 119.7(2) ?
C20 C21 C16 . . 121.18(19) ?
C23 C22 C27 . . 118.63(19) ?
C23 C22 P1 . . 126.05(15) ?
C27 C22 P1 . . 115.32(17) ?
C22 C23 C24 . . 120.8(2) ?
C25 C24 C23 . . 119.6(2) ?
C26 C25 C24 . . 120.4(2) ?
C25 C26 C27 . . 119.8(2) ?
C26 C27 C22 . . 120.7(2) ?
O1 C28 N1 . . 120.8(2) ?
O1 C28 C29 . . 121.88(19) ?
N1 C28 C29 . . 117.33(17) ?
C30 C29 C28 . . 121.8(2) ?
C29 C30 C31 . . 125.9(2) ?
C28 N1 C1 . . 120.57(17) ?
C28 N1 C8 . . 116.50(16) ?
C1 N1 C8 . . 122.34(15) ?
C22 P1 C16 . . 102.31(9) ?
C22 P1 C2 . . 104.66(9) ?
C16 P1 C2 . . 100.09(8) ?

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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6 C1 C2 C3 . . . . -1.1(3) ?
N1 C1 C2 C3 . . . . -178.85(16) ?
C6 C1 C2 P1 . . . . -178.60(14) ?
N1 C1 C2 P1 . . . . 3.6(2) ?
C1 C2 C3 C4 . . . . 0.7(3) ?
P1 C2 C3 C4 . . . . 178.11(15) ?
C2 C3 C4 C5 . . . . -0.5(3) ?
C3 C4 C5 C6 . . . . 0.8(3) ?
C4 C5 C6 C1 . . . . -1.1(3) ?
C4 C5 C6 C7 . . . . 177.80(18) ?
C2 C1 C6 C5 . . . . 1.3(3) ?
N1 C1 C6 C5 . . . . 179.08(16) ?
C2 C1 C6 C7 . . . . -177.63(18) ?
N1 C1 C6 C7 . . . . 0.2(3) ?
N1 C8 C10 C15 . . . . 121.64(19) ?
C9 C8 C10 C15 . . . . -111.9(2) ?
N1 C8 C10 C11 . . . . -65.4(2) ?
C9 C8 C10 C11 . . . . 61.0(2) ?
C15 C10 C11 C12 . . . . -0.2(3) ?
C8 C10 C11 C12 . . . . -173.12(19) ?
C10 C11 C12 C13 . . . . 1.1(3) ?
C11 C12 C13 C14 . . . . -1.0(4) ?
C12 C13 C14 C15 . . . . 0.2(4) ?
C11 C10 C15 C14 . . . . -0.7(3) ?
C8 C10 C15 C14 . . . . 172.55(19) ?
C13 C14 C15 C10 . . . . 0.7(3) ?
C21 C16 C17 C18 . . . . 0.1(3) ?
P1 C16 C17 C18 . . . . 174.07(19) ?
C16 C17 C18 C19 . . . . -0.1(4) ?
C17 C18 C19 C20 . . . . 0.1(4) ?
C18 C19 C20 C21 . . . . -0.1(4) ?
C19 C20 C21 C16 . . . . 0.1(3) ?
C17 C16 C21 C20 . . . . -0.1(3) ?
P1 C16 C21 C20 . . . . -174.56(17) ?
C27 C22 C23 C24 . . . . -1.2(3) ?
P1 C22 C23 C24 . . . . 178.34(17) ?
C22 C23 C24 C25 . . . . 1.3(3) ?
C23 C24 C25 C26 . . . . 0.1(3) ?
C24 C25 C26 C27 . . . . -1.6(3) ?
C25 C26 C27 C22 . . . . 1.7(3) ?
C23 C22 C27 C26 . . . . -0.3(3) ?
P1 C22 C27 C26 . . . . -179.89(16) ?
O1 C28 C29 C30 . . . . 12.8(3) ?
N1 C28 C29 C30 . . . . -167.0(2) ?
C28 C29 C30 C31 . . . . 176.8(2) ?
O1 C28 N1 C1 . . . . -174.32(17) ?
C29 C28 N1 C1 . . . . 5.5(2) ?
O1 C28 N1 C8 . . . . -3.0(3) ?
C29 C28 N1 C8 . . . . 176.84(16) ?
C2 C1 N1 C28 . . . . 86.7(2) ?
C6 C1 N1 C28 . . . . -91.2(2) ?
C2 C1 N1 C8 . . . . -84.2(2) ?
C6 C1 N1 C8 . . . . 98.0(2) ?
C10 C8 N1 C28 . . . . -158.25(16) ?
C9 C8 N1 C28 . . . . 75.7(2) ?
C10 C8 N1 C1 . . . . 12.9(2) ?
C9 C8 N1 C1 . . . . -113.06(19) ?
C23 C22 P1 C16 . . . . 93.69(17) ?
C27 C22 P1 C16 . . . . -86.73(16) ?
C23 C22 P1 C2 . . . . -10.34(19) ?
C27 C22 P1 C2 . . . . 169.24(14) ?
C17 C16 P1 C22 . . . . 5.8(2) ?
C21 C16 P1 C22 . . . . 179.83(15) ?
C17 C16 P1 C2 . . . . 113.34(18) ?
C21 C16 P1 C2 . . . . -72.59(16) ?
C3 C2 P1 C22 . . . . 79.09(17) ?
C1 C2 P1 C22 . . . . -103.45(15) ?
C3 C2 P1 C16 . . . . -26.60(17) ?
C1 C2 P1 C16 . . . . 150.86(15) ?


