# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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 2096845'
loop_
_audit_author_name
_audit_author_address
'Takashi MINO'
;Chiba University
Japan
;
_audit_update_record             
;
2021-07-16 deposited with the CCDC.	2021-11-12 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H32 N O P'
_chemical_formula_iupac          ?
_chemical_formula_weight         525.59
_chemical_absolute_configuration ad

_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                   8.3651(8)
_cell_length_b                   13.6367(13)
_cell_length_c                   25.424(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2900.2(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5281
_cell_measurement_theta_min      2.5632
_cell_measurement_theta_max      25.7156
_cell_measurement_temperature    173(2)

_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.300
_exptl_crystal_density_diffrn    1.204
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1112

_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_absorpt_correction_T_min  0.90
_exptl_absorpt_correction_T_max  0.96

_exptl_special_details           'SADABS (Sheldrick 1996)'

_diffrn_ambient_temperature      173(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

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

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            16777
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_unetI/netI     0.0352
_diffrn_reflns_theta_min         1.695
_diffrn_reflns_theta_max         27.548
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       32

_refine_special_details          
;
;

_reflns_number_total             6586
_reflns_number_gt                5705
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_gt          0.0793
_refine_ls_wR_factor_ref         0.0861
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_number_reflns         6586
_refine_ls_number_parameters     354
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0400P)²+0.3574P] 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         0.200
_refine_diff_density_min         -0.200
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack x determined using 2147 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.12(4)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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 0.3801(3) 0.33894(16) 0.64608(9) 0.0355(5) Uani d . . . 1 . .
C C2 0.5438(3) 0.29666(16) 0.64751(9) 0.0353(5) Uani d . . . 1 . .
H H2 0.631 0.3348 0.66 0.042 Uiso calc U . R 1 . .
C C3 0.5675(3) 0.20533(17) 0.63120(10) 0.0402(6) Uani d . . . 1 . .
H H3 0.4757 0.1719 0.6185 0.048 Uiso calc U . R 1 . .
C C4 0.7165(3) 0.14983(17) 0.63029(9) 0.0362(5) Uani d . . . 1 . .
C C5 0.8663(3) 0.19022(17) 0.64014(9) 0.0386(6) Uani d . . . 1 . .
H H5 0.875 0.2584 0.6473 0.046 Uiso calc U . R 1 . .
C C6 1.0020(3) 0.13335(17) 0.63964(9) 0.0433(5) Uani d . . . 1 . .
H H6 1.1029 0.1622 0.647 0.052 Uiso calc U . R 1 . .
C C7 0.9921(3) 0.03413(18) 0.62846(10) 0.0475(6) Uani d . . . 1 . .
H H7 1.086 -0.0051 0.6278 0.057 Uiso calc U . R 1 . .
C C8 0.8458(4) -0.00706(19) 0.61841(14) 0.0600(8) Uani d . . . 1 . .
H H8 0.8379 -0.0751 0.6109 0.072 Uiso calc U . R 1 . .
C C9 0.7100(3) 0.05031(19) 0.61923(12) 0.0538(7) Uani d . . . 1 . .
H H9 0.6094 0.0209 0.612 0.065 Uiso calc U . R 1 . .
C C10 0.1891(3) 0.46596(17) 0.66943(9) 0.0341(5) Uani d . . . 1 . .
H H10 0.1419 0.4466 0.6348 0.041 Uiso calc U . R 1 . .
C C11 0.1738(2) 0.57693(16) 0.67346(8) 0.0305(5) Uani d . . . 1 . .
C C12 0.1058(3) 0.62734(17) 0.63169(9) 0.0360(5) Uani d . . . 1 . .
H H12 0.0827 0.5934 0.6 0.043 Uiso calc U . R 1 . .
C C13 0.0709(3) 0.72676(18) 0.63554(11) 0.0443(6) Uani d . . . 1 . .
H H13 0.0225 0.76 0.6068 0.053 Uiso calc U . R 1 . .
C C14 0.1066(3) 0.77723(18) 0.68110(11) 0.0464(7) Uani d . . . 1 . .
H H14 0.0831 0.8452 0.6839 0.056 Uiso calc U . R 1 . .
C C15 0.1767(3) 0.72799(19) 0.72255(11) 0.0450(6) Uani d . . . 1 . .
H H15 0.2032 0.7628 0.7537 0.054 Uiso calc U . R 1 . .
C C16 0.2089(3) 0.62881(18) 0.71926(10) 0.0376(5) Uani d . . . 1 . .
H H16 0.2553 0.5958 0.7484 0.045 Uiso calc U . R 1 . .
C C17 0.0888(3) 0.41589(19) 0.71215(12) 0.0497(7) Uani d . . . 1 . .
H H17A 0.1042 0.3447 0.7102 0.075 Uiso calc U . R 1 . .
H H17B -0.0244 0.4314 0.7067 0.075 Uiso calc U . R 1 . .
H H17C 0.1225 0.4395 0.7468 0.075 Uiso calc U . R 1 . .
C C18 0.4873(3) 0.48524(14) 0.69049(8) 0.0275(4) Uani d . . . 1 . .
C C19 0.5609(2) 0.55332(17) 0.65719(8) 0.0289(4) Uani d . . . 1 . .
C C20 0.6795(3) 0.61430(18) 0.67766(9) 0.0371(5) Uani d . . . 1 . .
H H20 0.7284 0.6623 0.6559 0.045 Uiso calc U . R 1 . .
C C21 0.7263(3) 0.6049(2) 0.72979(10) 0.0439(6) Uani d . . . 1 . .
H H21 0.8058 0.6472 0.7438 0.053 Uiso calc U . R 1 . .
C C22 0.6575(3) 0.5343(2) 0.76120(9) 0.0431(6) Uani d . . . 1 . .
H H22 0.6931 0.5274 0.7965 0.052 Uiso calc U . R 1 . .
C C23 0.5370(3) 0.47261(17) 0.74272(8) 0.0346(5) Uani d . . . 1 . .
C C24 0.4674(4) 0.3943(2) 0.77752(10) 0.0532(7) Uani d . . . 1 . .
H H24A 0.3628 0.4158 0.7906 0.08 Uiso calc U . R 1 . .
H H24B 0.5392 0.3826 0.8073 0.08 Uiso calc U . R 1 . .
H H24C 0.4547 0.3336 0.7573 0.08 Uiso calc U . R 1 . .
C C25 0.5561(3) 0.67846(17) 0.56782(8) 0.0332(5) Uani d . . . 1 . .
C C26 0.4694(3) 0.75617(18) 0.58914(10) 0.0412(6) Uani d . . . 1 . .
H H26 0.3983 0.7443 0.6176 0.049 Uiso calc U . R 1 . .
C C27 0.4851(3) 0.85008(18) 0.56965(10) 0.0472(6) Uani d . . . 1 . .
H H27 0.4241 0.9019 0.5845 0.057 Uiso calc U . R 1 . .
C C28 0.5886(4) 0.8693(2) 0.52879(10) 0.0519(7) Uani d . . . 1 . .
H H28 0.5987 0.9339 0.5152 0.062 Uiso calc U . R 1 . .
C C29 0.6768(4) 0.7938(2) 0.50797(12) 0.0597(8) Uani d . . . 1 . .
H H29 0.7501 0.8068 0.4803 0.072 Uiso calc U . R 1 . .
C C30 0.6604(3) 0.6987(2) 0.52680(10) 0.0488(7) Uani d . . . 1 . .
H H30 0.7209 0.6471 0.5115 0.059 Uiso calc U . R 1 . .
C C31 0.6447(3) 0.47439(17) 0.55661(9) 0.0351(5) Uani d . . . 1 . .
C C32 0.5950(4) 0.4229(2) 0.51258(10) 0.0506(7) Uani d . . . 1 . .
H H32 0.4897 0.4321 0.4995 0.061 Uiso calc U . R 1 . .
C C33 0.6972(4) 0.3579(2) 0.48729(11) 0.0635(9) Uani d . . . 1 . .
H H33 0.6611 0.3227 0.4573 0.076 Uiso calc U . R 1 . .
C C34 0.8507(4) 0.3444(2) 0.50545(11) 0.0549(7) Uani d . . . 1 . .
H H34 0.921 0.3006 0.4878 0.066 Uiso calc U . R 1 . .
C C35 0.9016(3) 0.3946(2) 0.54932(11) 0.0501(7) Uani d . . . 1 . .
H H35 1.0071 0.385 0.5622 0.06 Uiso calc U . R 1 . .
C C36 0.8003(3) 0.45902(19) 0.57473(10) 0.0427(6) Uani d . . . 1 . .
H H36 0.8369 0.4933 0.6049 0.051 Uiso calc U . R 1 . .
N N1 0.3571(2) 0.42762(13) 0.67014(7) 0.0296(4) Uani d . . . 1 . .
O O1 0.2686(2) 0.29521(13) 0.62531(8) 0.0503(5) Uani d . . . 1 . .
P P1 0.49656(7) 0.55493(4) 0.58780(2) 0.03135(13) 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 O1 . 1.227(3) ?
C1 N1 . 1.369(3) ?
C1 C2 . 1.486(3) ?
C2 C3 . 1.327(3) ?
C2 H2 . 0.95 ?
C3 C4 . 1.458(4) ?
C3 H3 . 0.95 ?
C4 C9 . 1.387(3) ?
C4 C5 . 1.392(3) ?
C5 C6 . 1.375(4) ?
C5 H5 . 0.95 ?
C6 C7 . 1.385(3) ?
C6 H6 . 0.95 ?
C7 C8 . 1.371(4) ?
C7 H7 . 0.95 ?
C8 C9 . 1.379(4) ?
C8 H8 . 0.95 ?
C9 H9 . 0.95 ?
C10 N1 . 1.499(3) ?
C10 C11 . 1.522(3) ?
C10 C17 . 1.533(3) ?
C10 H10 . 1.0 ?
C11 C12 . 1.387(3) ?
C11 C16 . 1.394(3) ?
C12 C13 . 1.390(3) ?
C12 H12 . 0.95 ?
C13 C14 . 1.380(4) ?
C13 H13 . 0.95 ?
C14 C15 . 1.380(4) ?
C14 H14 . 0.95 ?
C15 C16 . 1.382(3) ?
C15 H15 . 0.95 ?
C16 H16 . 0.95 ?
C17 H17A . 0.98 ?
C17 H17B . 0.98 ?
C17 H17C . 0.98 ?
C18 C19 . 1.399(3) ?
C18 C23 . 1.402(3) ?
C18 N1 . 1.439(3) ?
C19 C20 . 1.396(3) ?
C19 P1 . 1.845(2) ?
C20 C21 . 1.388(3) ?
C20 H20 . 0.95 ?
C21 C22 . 1.377(4) ?
C21 H21 . 0.95 ?
C22 C23 . 1.394(3) ?
C22 H22 . 0.95 ?
C23 C24 . 1.504(3) ?
C24 H24A . 0.98 ?
C24 H24B . 0.98 ?
C24 H24C . 0.98 ?
C25 C30 . 1.387(3) ?
C25 C26 . 1.394(3) ?
C25 P1 . 1.829(2) ?
C26 C27 . 1.379(3) ?
C26 H26 . 0.95 ?
C27 C28 . 1.377(4) ?
C27 H27 . 0.95 ?
C28 C29 . 1.373(4) ?
C28 H28 . 0.95 ?
C29 C30 . 1.390(4) ?
C29 H29 . 0.95 ?
C30 H30 . 0.95 ?
C31 C32 . 1.385(3) ?
C31 C36 . 1.396(3) ?
C31 P1 . 1.836(2) ?
C32 C33 . 1.389(4) ?
C32 H32 . 0.95 ?
C33 C34 . 1.376(4) ?
C33 H33 . 0.95 ?
C34 C35 . 1.377(4) ?
C34 H34 . 0.95 ?
C35 C36 . 1.381(3) ?
C35 H35 . 0.95 ?
C36 H36 . 0.95 ?

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
O1 C1 N1 . . 121.0(2) ?
O1 C1 C2 . . 121.5(2) ?
N1 C1 C2 . . 117.5(2) ?
C3 C2 C1 . . 119.6(2) ?
C3 C2 H2 . . 120.2 ?
C1 C2 H2 . . 120.2 ?
C2 C3 C4 . . 128.3(2) ?
C2 C3 H3 . . 115.9 ?
C4 C3 H3 . . 115.9 ?
C9 C4 C5 . . 117.3(2) ?
C9 C4 C3 . . 118.5(2) ?
C5 C4 C3 . . 124.1(2) ?
C6 C5 C4 . . 121.2(2) ?
C6 C5 H5 . . 119.4 ?
C4 C5 H5 . . 119.4 ?
C5 C6 C7 . . 120.2(3) ?
C5 C6 H6 . . 119.9 ?
C7 C6 H6 . . 119.9 ?
C8 C7 C6 . . 119.5(3) ?
C8 C7 H7 . . 120.3 ?
C6 C7 H7 . . 120.3 ?
C7 C8 C9 . . 120.0(2) ?
C7 C8 H8 . . 120.0 ?
C9 C8 H8 . . 120.0 ?
C8 C9 C4 . . 121.7(2) ?
C8 C9 H9 . . 119.1 ?
C4 C9 H9 . . 119.1 ?
N1 C10 C11 . . 115.13(17) ?
N1 C10 C17 . . 110.43(19) ?
C11 C10 C17 . . 110.43(19) ?
N1 C10 H10 . . 106.8 ?
C11 C10 H10 . . 106.8 ?
C17 C10 H10 . . 106.8 ?
C12 C11 C16 . . 118.3(2) ?
C12 C11 C10 . . 118.4(2) ?
C16 C11 C10 . . 122.9(2) ?
C11 C12 C13 . . 121.0(2) ?
C11 C12 H12 . . 119.5 ?
C13 C12 H12 . . 119.5 ?
C14 C13 C12 . . 120.0(2) ?
C14 C13 H13 . . 120.0 ?
C12 C13 H13 . . 120.0 ?
C13 C14 C15 . . 119.4(2) ?
C13 C14 H14 . . 120.3 ?
C15 C14 H14 . . 120.3 ?
C14 C15 C16 . . 120.9(3) ?
C14 C15 H15 . . 119.6 ?
C16 C15 H15 . . 119.6 ?
C15 C16 C11 . . 120.4(2) ?
C15 C16 H16 . . 119.8 ?
C11 C16 H16 . . 119.8 ?
C10 C17 H17A . . 109.5 ?
C10 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
C10 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C19 C18 C23 . . 121.6(2) ?
C19 C18 N1 . . 118.53(18) ?
C23 C18 N1 . . 119.85(19) ?
C20 C19 C18 . . 118.86(19) ?
C20 C19 P1 . . 123.84(17) ?
C18 C19 P1 . . 117.28(15) ?
C21 C20 C19 . . 120.1(2) ?
C21 C20 H20 . . 119.9 ?
C19 C20 H20 . . 119.9 ?
C22 C21 C20 . . 120.0(2) ?
C22 C21 H21 . . 120.0 ?
C20 C21 H21 . . 120.0 ?
C21 C22 C23 . . 121.9(2) ?
C21 C22 H22 . . 119.0 ?
C23 C22 H22 . . 119.0 ?
C22 C23 C18 . . 117.3(2) ?
C22 C23 C24 . . 120.7(2) ?
C18 C23 C24 . . 122.0(2) ?
C23 C24 H24A . . 109.5 ?
C23 C24 H24B . . 109.5 ?
H24A C24 H24B . . 109.5 ?
C23 C24 H24C . . 109.5 ?
H24A C24 H24C . . 109.5 ?
H24B C24 H24C . . 109.5 ?
C30 C25 C26 . . 117.9(2) ?
C30 C25 P1 . . 124.3(2) ?
C26 C25 P1 . . 116.77(17) ?
C27 C26 C25 . . 121.1(2) ?
C27 C26 H26 . . 119.4 ?
C25 C26 H26 . . 119.4 ?
C28 C27 C26 . . 120.5(2) ?
C28 C27 H27 . . 119.8 ?
C26 C27 H27 . . 119.8 ?
C29 C28 C27 . . 119.1(3) ?
C29 C28 H28 . . 120.5 ?
C27 C28 H28 . . 120.5 ?
C28 C29 C30 . . 120.9(3) ?
C28 C29 H29 . . 119.5 ?
C30 C29 H29 . . 119.5 ?
C25 C30 C29 . . 120.4(3) ?
C25 C30 H30 . . 119.8 ?
C29 C30 H30 . . 119.8 ?
C32 C31 C36 . . 118.1(2) ?
C32 C31 P1 . . 116.71(19) ?
C36 C31 P1 . . 125.20(17) ?
C31 C32 C33 . . 120.8(3) ?
C31 C32 H32 . . 119.6 ?
C33 C32 H32 . . 119.6 ?
C34 C33 C32 . . 120.3(3) ?
C34 C33 H33 . . 119.9 ?
C32 C33 H33 . . 119.9 ?
C33 C34 C35 . . 119.6(3) ?
C33 C34 H34 . . 120.2 ?
C35 C34 H34 . . 120.2 ?
C34 C35 C36 . . 120.4(3) ?
C34 C35 H35 . . 119.8 ?
C36 C35 H35 . . 119.8 ?
C35 C36 C31 . . 120.9(2) ?
C35 C36 H36 . . 119.6 ?
C31 C36 H36 . . 119.6 ?
C1 N1 C18 . . 122.44(18) ?
C1 N1 C10 . . 115.76(18) ?
C18 N1 C10 . . 121.54(17) ?
C25 P1 C31 . . 104.30(11) ?
C25 P1 C19 . . 101.37(10) ?
C31 P1 C19 . . 102.07(10) ?

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
O1 C1 C2 C3 . . . . -7.4(4) ?
N1 C1 C2 C3 . . . . 170.8(2) ?
C1 C2 C3 C4 . . . . -178.7(2) ?
C2 C3 C4 C9 . . . . 170.2(3) ?
C2 C3 C4 C5 . . . . -9.5(4) ?
C9 C4 C5 C6 . . . . -0.9(4) ?
C3 C4 C5 C6 . . . . 178.7(2) ?
C4 C5 C6 C7 . . . . 1.0(4) ?
C5 C6 C7 C8 . . . . -0.7(4) ?
C6 C7 C8 C9 . . . . 0.3(5) ?
C7 C8 C9 C4 . . . . -0.3(5) ?
C5 C4 C9 C8 . . . . 0.6(4) ?
C3 C4 C9 C8 . . . . -179.1(3) ?
N1 C10 C11 C12 . . . . 117.3(2) ?
C17 C10 C11 C12 . . . . -116.9(2) ?
N1 C10 C11 C16 . . . . -69.9(3) ?
C17 C10 C11 C16 . . . . 56.0(3) ?
C16 C11 C12 C13 . . . . -1.0(3) ?
C10 C11 C12 C13 . . . . 172.1(2) ?
C11 C12 C13 C14 . . . . 1.2(4) ?
C12 C13 C14 C15 . . . . -0.1(4) ?
C13 C14 C15 C16 . . . . -1.1(4) ?
C14 C15 C16 C11 . . . . 1.3(4) ?
C12 C11 C16 C15 . . . . -0.2(3) ?
C10 C11 C16 C15 . . . . -173.0(2) ?
C23 C18 C19 C20 . . . . -4.2(3) ?
N1 C18 C19 C20 . . . . 175.52(19) ?
C23 C18 C19 P1 . . . . 174.60(16) ?
N1 C18 C19 P1 . . . . -5.7(3) ?
C18 C19 C20 C21 . . . . 1.9(3) ?
P1 C19 C20 C21 . . . . -176.77(19) ?
C19 C20 C21 C22 . . . . 1.1(4) ?
C20 C21 C22 C23 . . . . -2.0(4) ?
C21 C22 C23 C18 . . . . -0.2(3) ?
C21 C22 C23 C24 . . . . 178.3(2) ?
C19 C18 C23 C22 . . . . 3.3(3) ?
N1 C18 C23 C22 . . . . -176.39(19) ?
C19 C18 C23 C24 . . . . -175.2(2) ?
N1 C18 C23 C24 . . . . 5.1(3) ?
C30 C25 C26 C27 . . . . 0.8(4) ?
P1 C25 C26 C27 . . . . -168.17(19) ?
C25 C26 C27 C28 . . . . -0.6(4) ?
C26 C27 C28 C29 . . . . -0.5(4) ?
C27 C28 C29 C30 . . . . 1.4(5) ?
C26 C25 C30 C29 . . . . 0.1(4) ?
P1 C25 C30 C29 . . . . 168.2(2) ?
C28 C29 C30 C25 . . . . -1.2(5) ?
C36 C31 C32 C33 . . . . 0.0(4) ?
P1 C31 C32 C33 . . . . -178.0(2) ?
C31 C32 C33 C34 . . . . -0.6(5) ?
C32 C33 C34 C35 . . . . 0.9(5) ?
C33 C34 C35 C36 . . . . -0.7(5) ?
C34 C35 C36 C31 . . . . 0.1(4) ?
C32 C31 C36 C35 . . . . 0.2(4) ?
P1 C31 C36 C35 . . . . 178.1(2) ?
O1 C1 N1 C18 . . . . -174.0(2) ?
C2 C1 N1 C18 . . . . 7.8(3) ?
O1 C1 N1 C10 . . . . 0.3(3) ?
C2 C1 N1 C10 . . . . -177.95(19) ?
C19 C18 N1 C1 . . . . 89.8(2) ?
C23 C18 N1 C1 . . . . -90.5(3) ?
C19 C18 N1 C10 . . . . -84.1(2) ?
C23 C18 N1 C10 . . . . 95.6(2) ?
C11 C10 N1 C1 . . . . -154.45(19) ?
C17 C10 N1 C1 . . . . 79.7(2) ?
C11 C10 N1 C18 . . . . 19.9(3) ?
C17 C10 N1 C18 . . . . -106.0(2) ?
C30 C25 P1 C31 . . . . 16.1(2) ?
C26 C25 P1 C31 . . . . -175.70(19) ?
C30 C25 P1 C19 . . . . 121.8(2) ?
C26 C25 P1 C19 . . . . -70.0(2) ?
C32 C31 P1 C25 . . . . -104.3(2) ?
C36 C31 P1 C25 . . . . 77.9(2) ?
C32 C31 P1 C19 . . . . 150.5(2) ?
C36 C31 P1 C19 . . . . -27.4(2) ?
C20 C19 P1 C25 . . . . -23.1(2) ?
C18 C19 P1 C25 . . . . 158.18(17) ?
C20 C19 P1 C31 . . . . 84.4(2) ?
C18 C19 P1 C31 . . . . -94.32(18) ?
####################################################################### 
# 
# 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 2096846'
loop_
_audit_author_name
_audit_author_address
'Takashi MINO'
;Chiba University
Japan
;
_audit_update_record             
;
2021-07-16 deposited with the CCDC.	2021-11-12 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H32 N O P'
_chemical_formula_iupac          ?
_chemical_formula_weight         525.59
_chemical_absolute_configuration ad

_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                   8.631(3)
_cell_length_b                   11.371(4)
_cell_length_c                   29.685(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2913.4(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1587
_cell_measurement_theta_min      2.2562
_cell_measurement_theta_max      18.4213
_cell_measurement_temperature    173(2)

_exptl_crystal_description       Needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1112

_exptl_absorpt_coefficient_mu    0.123
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'SADABS (Sheldrick 1996)'
_exptl_absorpt_correction_T_min  0.67
_exptl_absorpt_correction_T_max  0.99

_exptl_special_details           'SADABS (Sheldrick 1996)'

_diffrn_ambient_temperature      173(2)

_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  graphite

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

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            16838
_diffrn_reflns_av_R_equivalents  0.0811
_diffrn_reflns_av_unetI/netI     0.1242
_diffrn_reflns_theta_min         1.372
_diffrn_reflns_theta_max         27.736
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       38

_refine_special_details          
;
;

_reflns_number_total             6641
_reflns_number_gt                3660
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1559
_refine_ls_R_factor_gt           0.0846
_refine_ls_wR_factor_gt          0.1943
_refine_ls_wR_factor_ref         0.2330
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.074
_refine_ls_number_reflns         6641
_refine_ls_number_parameters     410
_refine_ls_number_restraints     508
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0997P)²+1.4536P] 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         0.408
_refine_diff_density_min         -0.592
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;
Flack x determined using 1049 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(11)

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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 C11A 0.1159(15) 0.4076(14) 0.6456(5) 0.0447(12) Uani d U P . 0.558(13) A 1
H H11A 0.1308 0.432 0.6142 0.067 Uiso calc U P R 0.558(13) A 1
H H11B 0.0051 0.3958 0.6514 0.067 Uiso calc U P R 0.558(13) A 1
H H11C 0.1716 0.3338 0.651 0.067 Uiso calc U P R 0.558(13) A 1
C C13A 0.2104(17) 0.3810(15) 0.7434(5) 0.0458(8) Uani d U P . 0.558(13) A 1
H H13A 0.2595 0.3246 0.7246 0.055 Uiso calc U P R 0.558(13) A 1
C C14A 0.1923(15) 0.3602(15) 0.7890(5) 0.0462(8) Uani d U P . 0.558(13) A 1
H H14A 0.234 0.2906 0.8019 0.055 Uiso calc U P R 0.558(13) A 1
C C15A 0.1135(16) 0.4401(16) 0.8163(5) 0.0463(8) Uani d U P . 0.558(13) A 1
H H15A 0.0989 0.423 0.8474 0.056 Uiso calc U P R 0.558(13) A 1
C C16A 0.0591(17) 0.5392(14) 0.7995(5) 0.0460(8) Uani d U P . 0.558(13) A 1
H H16A 0.007 0.5944 0.8181 0.055 Uiso calc U P R 0.558(13) A 1
C C17A 0.080(2) 0.5611(17) 0.7533(6) 0.0456(8) Uani d U P . 0.558(13) A 1
H H17A 0.0393 0.6318 0.7409 0.055 Uiso calc U P R 0.558(13) A 1
C C11B 0.1448(19) 0.3621(17) 0.6568(6) 0.0445(12) Uani d U P . 0.442(13) A 2
H H11D 0.1603 0.3596 0.6242 0.067 Uiso calc U P R 0.442(13) A 2
H H11E 0.0386 0.3381 0.664 0.067 Uiso calc U P R 0.442(13) A 2
H H11F 0.218 0.3085 0.6715 0.067 Uiso calc U P R 0.442(13) A 2
C C13B 0.215(2) 0.4030(19) 0.7569(6) 0.0458(8) Uani d U P . 0.442(13) A 2
H H13B 0.2782 0.3414 0.7455 0.055 Uiso calc U P R 0.442(13) A 2
C C14B 0.187(2) 0.4060(19) 0.8022(7) 0.0461(8) Uani d U P . 0.442(13) A 2
H H14B 0.2206 0.3427 0.8207 0.055 Uiso calc U P R 0.442(13) A 2
C C15B 0.113(2) 0.497(2) 0.8206(7) 0.0462(8) Uani d U P . 0.442(13) A 2
H H15B 0.1042 0.5029 0.8524 0.055 Uiso calc U P R 0.442(13) A 2
C C16B 0.048(2) 0.5860(18) 0.7923(6) 0.0460(8) Uani d U P . 0.442(13) A 2
H H16B -0.0113 0.6477 0.8052 0.055 Uiso calc U P R 0.442(13) A 2
C C17B 0.071(3) 0.583(2) 0.7447(8) 0.0457(8) Uani d U P . 0.442(13) A 2
H H17B 0.0323 0.6437 0.726 0.055 Uiso calc U P R 0.442(13) A 2
C C1 0.3410(8) 0.6232(6) 0.6284(2) 0.0439(6) Uani d U . . 1.0 . .
C C2 0.4984(7) 0.6641(6) 0.6155(2) 0.0440(7) Uani d U . . 1.0 . .
H H2 0.5867 0.6362 0.6314 0.053 Uiso calc U . R 1.0 . .
C C3 0.5155(8) 0.7396(6) 0.5819(2) 0.0447(7) Uani d U . . 1.0 . .
H H3 0.4227 0.7662 0.5681 0.054 Uiso calc U . R 1.0 . .
C C4 0.6602(8) 0.7871(6) 0.5634(2) 0.0456(7) Uani d U . . 1.0 . .
C C5 0.8066(8) 0.7556(6) 0.5786(2) 0.0459(8) Uani d U . . 1.0 . .
H H5 0.8157 0.7029 0.6033 0.055 Uiso calc U . R 1.0 . .
C C6 0.9395(8) 0.7994(6) 0.5587(2) 0.0470(8) Uani d U . . 1.0 . .
H H6 1.0385 0.7764 0.5695 0.056 Uiso calc U . R 1.0 . .
C C7 0.9274(9) 0.8775(6) 0.5227(2) 0.0480(8) Uani d U . . 1.0 . .
H H7 1.0182 0.9067 0.5085 0.058 Uiso calc U . R 1.0 . .
C C8 0.7823(8) 0.9126(7) 0.5076(2) 0.0483(8) Uani d U . . 1.0 . .
H H8 0.7731 0.9671 0.4835 0.058 Uiso calc U . R 1.0 . .
C C9 0.6511(8) 0.8673(6) 0.5281(2) 0.0471(8) Uani d U . . 1.0 . .
H H9 0.5521 0.8918 0.5177 0.057 Uiso calc U . R 1.0 . .
C C10 0.1745(8) 0.4971(7) 0.6752(2) 0.0441(7) Uani d U . . 1.0 . .
H H10 0.1074 0.5662 0.6678 0.053 Uiso calc U . R 1.0 A 1
C C12 0.1552(8) 0.4860(7) 0.7257(2) 0.0452(7) Uani d U . . 1.0 . .
C C18 0.4713(7) 0.4867(6) 0.6799(2) 0.0396(5) Uani d U . . 1.0 . .
C C19 0.5462(7) 0.3925(6) 0.6578(2) 0.0391(5) Uani d U . . 1.0 . .
C C20 0.6819(7) 0.3479(6) 0.6769(2) 0.0387(6) Uani d U . . 1.0 . .
H H20 0.7349 0.285 0.6626 0.046 Uiso calc U . R 1.0 . .
C C21 0.7398(7) 0.3945(6) 0.7165(2) 0.0392(7) Uani d U . . 1.0 . .
H H21 0.8294 0.3606 0.7299 0.047 Uiso calc U . R 1.0 . .
C C22 0.6691(7) 0.4899(6) 0.7370(2) 0.0399(7) Uani d U . . 1.0 . .
H H22 0.7128 0.5227 0.7635 0.048 Uiso calc U . R 1.0 . .
C C23 0.5333(7) 0.5385(6) 0.7188(2) 0.0401(6) Uani d U . . 1.0 . .
C C24 0.4675(7) 0.6485(6) 0.7389(2) 0.0450(11) Uani d U . . 1.0 . .
H H24A 0.4498 0.7065 0.715 0.067 Uiso calc U . R 1.0 . .
H H24B 0.5405 0.6806 0.761 0.067 Uiso calc U . R 1.0 . .
H H24C 0.3691 0.6304 0.7539 0.067 Uiso calc U . R 1.0 . .
C C25 0.6712(8) 0.3272(7) 0.5745(2) 0.0458(6) Uani d U . . 1.0 . .
C C26 0.7405(8) 0.2222(7) 0.5615(2) 0.0484(7) Uani d U . . 1.0 . .
H H26 0.6909 0.1494 0.5678 0.058 Uiso calc U . R 1.0 . .
C C27 0.8833(8) 0.2234(7) 0.5391(3) 0.0511(8) Uani d U . . 1.0 . .
H H27 0.9293 0.1512 0.5302 0.061 Uiso calc U . R 1.0 . .
C C28 0.9563(8) 0.3247(6) 0.5301(2) 0.0528(8) Uani d U . . 1.0 . .
H H28 1.0531 0.324 0.5149 0.063 Uiso calc U . R 1.0 . .
C C29 0.8910(9) 0.4287(7) 0.5428(3) 0.0526(8) Uani d U . . 1.0 . .
H H29 0.9442 0.5004 0.5373 0.063 Uiso calc U . R 1.0 . .
C C30 0.7473(8) 0.4305(7) 0.5637(2) 0.0499(7) Uani d U . . 1.0 . .
H H30 0.7003 0.5038 0.5707 0.06 Uiso calc U . R 1.0 . .
C C31 0.4195(8) 0.1913(6) 0.6105(2) 0.0468(6) Uani d U . . 1.0 . .
C C32 0.4878(9) 0.1101(6) 0.6390(2) 0.0494(7) Uani d U . . 1.0 . .
H H32 0.5787 0.1314 0.6552 0.059 Uiso calc U . R 1.0 . .
C C33 0.4255(9) -0.0032(7) 0.6446(3) 0.0520(8) Uani d U . . 1.0 . .
H H33 0.4735 -0.0579 0.6644 0.062 Uiso calc U . R 1.0 . .
C C34 0.2935(9) -0.0341(7) 0.6210(3) 0.0530(8) Uani d U . . 1.0 . .
H H34 0.2502 -0.1102 0.6248 0.064 Uiso calc U . R 1.0 . .
C C35 0.2260(9) 0.0423(7) 0.5927(3) 0.0529(8) Uani d U . . 1.0 . .
H H35 0.1351 0.0201 0.5768 0.064 Uiso calc U . R 1.0 . .
C C36 0.2889(8) 0.1547(7) 0.5866(2) 0.0505(7) Uani d U . . 1.0 . .
H H36 0.2418 0.2071 0.5657 0.061 Uiso calc U . R 1.0 . .
N N1 0.3320(6) 0.5383(5) 0.66106(19) 0.0420(6) Uani d U . . 1.0 . .
O O1 0.2227(5) 0.6646(5) 0.61103(16) 0.0524(10) Uani d U . . 1.0 . .
P P1 0.48073(19) 0.34319(16) 0.60128(6) 0.0409(4) Uani d U . . 1.0 . .


_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
C11A C10 . 1.437(15) ?
C11A H11A . 0.98 ?
C11A H11B . 0.98 ?
C11A H11C . 0.98 ?
C13A C14A . 1.38(2) ?
C13A C12 . 1.389(18) ?
C13A H13A . 0.95 ?
C14A C15A . 1.394(19) ?
C14A H14A . 0.95 ?
C15A C16A . 1.32(2) ?
C15A H15A . 0.95 ?
C16A C17A . 1.41(2) ?
C16A H16A . 0.95 ?
C17A C12 . 1.35(2) ?
C17A H17A . 0.95 ?
C11B C10 . 1.648(19) ?
C11B H11D . 0.98 ?
C11B H11E . 0.98 ?
C11B H11F . 0.98 ?
C13B C14B . 1.37(3) ?
C13B C12 . 1.42(2) ?
C13B H13B . 0.95 ?
C14B C15B . 1.33(3) ?
C14B H14B . 0.95 ?
C15B C16B . 1.43(3) ?
C15B H15B . 0.95 ?
C16B C17B . 1.43(3) ?
C16B H16B . 0.95 ?
C17B C12 . 1.43(3) ?
C17B H17B . 0.95 ?
C1 O1 . 1.237(8) ?
C1 N1 . 1.369(9) ?
C1 C2 . 1.487(9) ?
C2 C3 . 1.324(9) ?
C2 H2 . 0.95 ?
C3 C4 . 1.468(10) ?
C3 H3 . 0.95 ?
C4 C5 . 1.390(10) ?
C4 C9 . 1.392(10) ?
C5 C6 . 1.383(10) ?
C5 H5 . 0.95 ?
C6 C7 . 1.394(10) ?
C6 H6 . 0.95 ?
C7 C8 . 1.388(10) ?
C7 H7 . 0.95 ?
C8 C9 . 1.384(10) ?
C8 H8 . 0.95 ?
C9 H9 . 0.95 ?
C10 N1 . 1.497(8) ?
C10 C12 . 1.513(10) ?
C10 H10 . 1.0 ?
C18 C23 . 1.403(9) ?
C18 C19 . 1.413(9) ?
C18 N1 . 1.450(8) ?
C19 C20 . 1.397(9) ?
C19 P1 . 1.856(7) ?
C20 C21 . 1.382(9) ?
C20 H20 . 0.95 ?
C21 C22 . 1.385(9) ?
C21 H21 . 0.95 ?
C22 C23 . 1.403(9) ?
C22 H22 . 0.95 ?
C23 C24 . 1.498(9) ?
C24 H24A . 0.98 ?
C24 H24B . 0.98 ?
C24 H24C . 0.98 ?
C25 C30 . 1.383(10) ?
C25 C26 . 1.391(10) ?
C25 P1 . 1.836(7) ?
C26 C27 . 1.400(10) ?
C26 H26 . 0.95 ?
C27 C28 . 1.340(10) ?
C27 H27 . 0.95 ?
C28 C29 . 1.364(10) ?
C28 H28 . 0.95 ?
C29 C30 . 1.387(10) ?
C29 H29 . 0.95 ?
C30 H30 . 0.95 ?
C31 C32 . 1.384(10) ?
C31 C36 . 1.397(10) ?
C31 P1 . 1.826(8) ?
C32 C33 . 1.406(10) ?
C32 H32 . 0.95 ?
C33 C34 . 1.383(11) ?
C33 H33 . 0.95 ?
C34 C35 . 1.340(11) ?
C34 H34 . 0.95 ?
C35 C36 . 1.401(10) ?
C35 H35 . 0.95 ?
C36 H36 . 0.95 ?

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
C10 C11A H11A . . 109.5 ?
C10 C11A H11B . . 109.5 ?
H11A C11A H11B . . 109.5 ?
C10 C11A H11C . . 109.5 ?
H11A C11A H11C . . 109.5 ?
H11B C11A H11C . . 109.5 ?
C14A C13A C12 . . 118.6(13) ?
C14A C13A H13A . . 120.7 ?
C12 C13A H13A . . 120.7 ?
C13A C14A C15A . . 120.9(14) ?
C13A C14A H14A . . 119.6 ?
C15A C14A H14A . . 119.6 ?
C16A C15A C14A . . 120.6(15) ?
C16A C15A H15A . . 119.7 ?
C14A C15A H15A . . 119.7 ?
C15A C16A C17A . . 118.4(15) ?
C15A C16A H16A . . 120.8 ?
C17A C16A H16A . . 120.8 ?
C12 C17A C16A . . 122.8(13) ?
C12 C17A H17A . . 118.6 ?
C16A C17A H17A . . 118.6 ?
C10 C11B H11D . . 109.5 ?
C10 C11B H11E . . 109.5 ?
H11D C11B H11E . . 109.5 ?
C10 C11B H11F . . 109.5 ?
H11D C11B H11F . . 109.5 ?
H11E C11B H11F . . 109.5 ?
C14B C13B C12 . . 124.2(16) ?
C14B C13B H13B . . 117.9 ?
C12 C13B H13B . . 117.9 ?
C15B C14B C13B . . 120.4(19) ?
C15B C14B H14B . . 119.8 ?
C13B C14B H14B . . 119.8 ?
C14B C15B C16B . . 119.8(18) ?
C14B C15B H15B . . 120.1 ?
C16B C15B H15B . . 120.1 ?
C17B C16B C15B . . 120.5(17) ?
C17B C16B H16B . . 119.7 ?
C15B C16B H16B . . 119.7 ?
C16B C17B C12 . . 118.8(15) ?
C16B C17B H17B . . 120.6 ?
C12 C17B H17B . . 120.6 ?
O1 C1 N1 . . 121.1(6) ?
O1 C1 C2 . . 121.8(6) ?
N1 C1 C2 . . 117.1(6) ?
C3 C2 C1 . . 119.9(6) ?
C3 C2 H2 . . 120.0 ?
C1 C2 H2 . . 120.0 ?
C2 C3 C4 . . 128.0(7) ?
C2 C3 H3 . . 116.0 ?
C4 C3 H3 . . 116.0 ?
C5 C4 C9 . . 117.8(7) ?
C5 C4 C3 . . 123.8(6) ?
C9 C4 C3 . . 118.4(6) ?
C6 C5 C4 . . 121.4(7) ?
C6 C5 H5 . . 119.3 ?
C4 C5 H5 . . 119.3 ?
C5 C6 C7 . . 119.7(7) ?
C5 C6 H6 . . 120.1 ?
C7 C6 H6 . . 120.1 ?
C8 C7 C6 . . 119.8(7) ?
C8 C7 H7 . . 120.1 ?
C6 C7 H7 . . 120.1 ?
C9 C8 C7 . . 119.4(7) ?
C9 C8 H8 . . 120.3 ?
C7 C8 H8 . . 120.3 ?
C8 C9 C4 . . 121.8(7) ?
C8 C9 H9 . . 119.1 ?
C4 C9 H9 . . 119.1 ?
C11A C10 N1 . . 111.8(7) ?
C11A C10 C12 . . 120.5(9) ?
N1 C10 C12 . . 113.8(5) ?
N1 C10 C11B . . 109.9(8) ?
C12 C10 C11B . . 103.4(9) ?
C11A C10 H10 . . 102.6 ?
N1 C10 H10 . . 102.6 ?
C12 C10 H10 . . 102.6 ?
C17A C12 C13A . . 118.6(10) ?
C13B C12 C17B . . 115.9(12) ?
C17A C12 C10 . . 126.9(9) ?
C13A C12 C10 . . 114.2(9) ?
C13B C12 C10 . . 131.4(10) ?
C17B C12 C10 . . 112.4(10) ?
C23 C18 C19 . . 121.7(6) ?
C23 C18 N1 . . 117.6(6) ?
C19 C18 N1 . . 120.5(6) ?
C20 C19 C18 . . 118.0(6) ?
C20 C19 P1 . . 120.9(5) ?
C18 C19 P1 . . 120.6(5) ?
C21 C20 C19 . . 120.7(7) ?
C21 C20 H20 . . 119.7 ?
C19 C20 H20 . . 119.7 ?
C20 C21 C22 . . 120.9(6) ?
C20 C21 H21 . . 119.6 ?
C22 C21 H21 . . 119.6 ?
C21 C22 C23 . . 120.6(6) ?
C21 C22 H22 . . 119.7 ?
C23 C22 H22 . . 119.7 ?
C22 C23 C18 . . 118.0(6) ?
C22 C23 C24 . . 119.5(6) ?
C18 C23 C24 . . 122.2(6) ?
C23 C24 H24A . . 109.5 ?
C23 C24 H24B . . 109.5 ?
H24A C24 H24B . . 109.5 ?
C23 C24 H24C . . 109.5 ?
H24A C24 H24C . . 109.5 ?
H24B C24 H24C . . 109.5 ?
C30 C25 C26 . . 117.5(6) ?
C30 C25 P1 . . 116.2(6) ?
C26 C25 P1 . . 126.2(6) ?
C25 C26 C27 . . 120.1(7) ?
C25 C26 H26 . . 120.0 ?
C27 C26 H26 . . 120.0 ?
C28 C27 C26 . . 121.2(7) ?
C28 C27 H27 . . 119.4 ?
C26 C27 H27 . . 119.4 ?
C27 C28 C29 . . 119.7(7) ?
C27 C28 H28 . . 120.2 ?
C29 C28 H28 . . 120.2 ?
C28 C29 C30 . . 120.4(7) ?
C28 C29 H29 . . 119.8 ?
C30 C29 H29 . . 119.8 ?
C25 C30 C29 . . 121.0(7) ?
C25 C30 H30 . . 119.5 ?
C29 C30 H30 . . 119.5 ?
C32 C31 C36 . . 117.1(7) ?
C32 C31 P1 . . 126.8(5) ?
C36 C31 P1 . . 116.0(6) ?
C31 C32 C33 . . 121.4(7) ?
C31 C32 H32 . . 119.3 ?
C33 C32 H32 . . 119.3 ?
C34 C33 C32 . . 119.2(8) ?
C34 C33 H33 . . 120.4 ?
C32 C33 H33 . . 120.4 ?
C35 C34 C33 . . 120.7(8) ?
C35 C34 H34 . . 119.6 ?
C33 C34 H34 . . 119.6 ?
C34 C35 C36 . . 120.3(7) ?
C34 C35 H35 . . 119.8 ?
C36 C35 H35 . . 119.8 ?
C31 C36 C35 . . 121.2(7) ?
C31 C36 H36 . . 119.4 ?
C35 C36 H36 . . 119.4 ?
C1 N1 C18 . . 120.7(5) ?
C1 N1 C10 . . 118.0(5) ?
C18 N1 C10 . . 121.2(5) ?
C31 P1 C25 . . 103.3(3) ?
C31 P1 C19 . . 103.7(3) ?
C25 P1 C19 . . 98.6(3) ?

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
C12 C13A C14A C15A . . . . 3.(2) ?
C13A C14A C15A C16A . . . . -2.(2) ?
C14A C15A C16A C17A . . . . 1.(2) ?
C15A C16A C17A C12 . . . . -1.(2) ?
C12 C13B C14B C15B . . . . -7.(3) ?
C13B C14B C15B C16B . . . . 7.(3) ?
C14B C15B C16B C17B . . . . -5.(3) ?
C15B C16B C17B C12 . . . . 3.(3) ?
O1 C1 C2 C3 . . . . -5.9(10) ?
N1 C1 C2 C3 . . . . 175.0(6) ?
C1 C2 C3 C4 . . . . -177.9(7) ?
C2 C3 C4 C5 . . . . 1.7(12) ?
C2 C3 C4 C9 . . . . -179.1(7) ?
C9 C4 C5 C6 . . . . -2.0(11) ?
C3 C4 C5 C6 . . . . 177.3(7) ?
C4 C5 C6 C7 . . . . 0.5(11) ?
C5 C6 C7 C8 . . . . 1.3(11) ?
C6 C7 C8 C9 . . . . -1.4(11) ?
C7 C8 C9 C4 . . . . -0.2(11) ?
C5 C4 C9 C8 . . . . 1.8(11) ?
C3 C4 C9 C8 . . . . -177.5(7) ?
C16A C17A C12 C13A . . . . 2.(2) ?
C16A C17A C12 C10 . . . . 175.6(12) ?
C14A C13A C12 C17A . . . . -3.0(19) ?
C14A C13A C12 C10 . . . . -177.4(10) ?
C14B C13B C12 C17B . . . . 5.(2) ?
C14B C13B C12 C10 . . . . 179.3(13) ?
C16B C17B C12 C13B . . . . -3.(2) ?
C16B C17B C12 C10 . . . . -178.2(16) ?
C11A C10 C12 C17A . . . . -120.0(15) ?
N1 C10 C12 C17A . . . . 103.1(13) ?
C11A C10 C12 C13A . . . . 53.8(12) ?
N1 C10 C12 C13A . . . . -83.0(10) ?
N1 C10 C12 C13B . . . . -72.5(14) ?
C11B C10 C12 C13B . . . . 46.6(14) ?
N1 C10 C12 C17B . . . . 101.8(12) ?
C11B C10 C12 C17B . . . . -139.0(13) ?
C23 C18 C19 C20 . . . . 2.8(10) ?
N1 C18 C19 C20 . . . . 178.6(6) ?
C23 C18 C19 P1 . . . . -169.3(5) ?
N1 C18 C19 P1 . . . . 6.6(9) ?
C18 C19 C20 C21 . . . . 0.5(10) ?
P1 C19 C20 C21 . . . . 172.5(5) ?
C19 C20 C21 C22 . . . . -3.1(10) ?
C20 C21 C22 C23 . . . . 2.5(10) ?
C21 C22 C23 C18 . . . . 0.7(10) ?
C21 C22 C23 C24 . . . . -174.1(6) ?
C19 C18 C23 C22 . . . . -3.4(10) ?
N1 C18 C23 C22 . . . . -179.3(6) ?
C19 C18 C23 C24 . . . . 171.3(6) ?
N1 C18 C23 C24 . . . . -4.6(9) ?
C30 C25 C26 C27 . . . . 1.2(11) ?
P1 C25 C26 C27 . . . . 176.6(6) ?
C25 C26 C27 C28 . . . . 0.4(12) ?
C26 C27 C28 C29 . . . . 0.1(12) ?
C27 C28 C29 C30 . . . . -2.1(12) ?
C26 C25 C30 C29 . . . . -3.3(11) ?
P1 C25 C30 C29 . . . . -179.2(6) ?
C28 C29 C30 C25 . . . . 3.8(12) ?
C36 C31 C32 C33 . . . . -1.9(11) ?
P1 C31 C32 C33 . . . . 177.3(6) ?
C31 C32 C33 C34 . . . . 0.2(11) ?
C32 C33 C34 C35 . . . . 0.6(11) ?
C33 C34 C35 C36 . . . . 0.3(12) ?
C32 C31 C36 C35 . . . . 2.8(10) ?
P1 C31 C36 C35 . . . . -176.5(6) ?
C34 C35 C36 C31 . . . . -2.1(11) ?
O1 C1 N1 C18 . . . . 177.3(6) ?
C2 C1 N1 C18 . . . . -3.6(9) ?
O1 C1 N1 C10 . . . . -0.1(10) ?
C2 C1 N1 C10 . . . . 179.0(6) ?
C23 C18 N1 C1 . . . . 92.2(8) ?
C19 C18 N1 C1 . . . . -83.9(8) ?
C23 C18 N1 C10 . . . . -90.5(8) ?
C19 C18 N1 C10 . . . . 93.5(8) ?
C11A C10 N1 C1 . . . . 83.9(10) ?
C12 C10 N1 C1 . . . . -135.5(6) ?
C11B C10 N1 C1 . . . . 109.1(10) ?
C11A C10 N1 C18 . . . . -93.5(10) ?
C12 C10 N1 C18 . . . . 47.1(9) ?
C11B C10 N1 C18 . . . . -68.3(10) ?
C32 C31 P1 C25 . . . . 65.7(7) ?
C36 C31 P1 C25 . . . . -115.1(6) ?
C32 C31 P1 C19 . . . . -36.8(7) ?
C36 C31 P1 C19 . . . . 142.4(5) ?
C30 C25 P1 C31 . . . . -179.5(6) ?
C26 C25 P1 C31 . . . . 5.0(7) ?
C30 C25 P1 C19 . . . . -73.1(6) ?
C26 C25 P1 C19 . . . . 111.4(7) ?
C20 C19 P1 C31 . . . . 70.1(6) ?
C18 C19 P1 C31 . . . . -118.1(6) ?
C20 C19 P1 C25 . . . . -36.0(6) ?
C18 C19 P1 C25 . . . . 135.8(6) ?
