# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_publication_text
_database_code_depnum_ccdc_archive 'CCDC 1040791'
_audit_update_record             
;
2015-02-24 deposited with the CCDC.
2016-01-07 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H28 N3 O6 P'
_chemical_formula_weight         629.58

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C c'
_space_group_name_Hall           'C -2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   12.087(3)
_cell_length_b                   21.192(5)
_cell_length_c                   12.419(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.461(5)
_cell_angle_gamma                90
_cell_volume                     3175.3(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7916
_cell_measurement_theta_min      2.4775
_cell_measurement_theta_max      26.5149

_exptl_crystal_description       Lump
_exptl_crystal_colour            Orange
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             1312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.138
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8994
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            12751
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_av_R_equivalents  0.0242
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.922
_diffrn_reflns_theta_max         26.589
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.797
_diffrn_reflns_point_group_measured_fraction_full 0.822
_reflns_number_total             5289
_reflns_number_gt                5152
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.605
_reflns_Friedel_fraction_max     0.602
_reflns_Friedel_fraction_full    0.645

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0310P)²+1.1097P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1893 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5289
_refine_ls_number_parameters     417
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0259
_refine_ls_wR_factor_ref         0.0627
_refine_ls_wR_factor_gt          0.0619
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 1.40236(17) 0.01655(9) 0.28680(18) 0.0188(4) Uani 1 1 d . . . . .
C2 C 1.40919(18) 0.06707(10) 0.35698(19) 0.0219(5) Uani 1 1 d . . . . .
H18 H 1.4736 0.0739 0.4032 0.026 Uiso 1 1 calc R U . . .
C3 C 1.22483(17) 0.09793(9) 0.28983(17) 0.0152(4) Uani 1 1 d . . . . .
C4 C 1.12518(16) 0.14119(9) 0.28910(16) 0.0140(4) Uani 1 1 d . . . . .
H17 H 1.0997 0.1476 0.2118 0.017 Uiso 1 1 calc R U . . .
C5 C 1.02340(16) 0.11389(9) 0.34733(16) 0.0138(4) Uani 1 1 d . . . . .
C6 C 0.95070(17) 0.17419(9) 0.35639(17) 0.0145(4) Uani 1 1 d . . . . .
C7 C 0.83020(17) 0.17216(9) 0.35056(16) 0.0149(4) Uani 1 1 d . . . . .
C8 C 0.63911(17) 0.17505(9) 0.19435(16) 0.0152(4) Uani 1 1 d . . . . .
C9 C 0.53690(19) 0.20336(10) 0.16923(18) 0.0199(4) Uani 1 1 d . . . . .
H3 H 0.5234 0.2452 0.1926 0.024 Uiso 1 1 calc R U . . .
C10 C 0.45486(19) 0.17046(11) 0.11009(19) 0.0247(5) Uani 1 1 d . . . . .
H4 H 0.3848 0.1897 0.0939 0.030 Uiso 1 1 calc R U . . .
C11 C 0.47416(19) 0.11006(11) 0.07459(19) 0.0246(5) Uani 1 1 d . . . . .
H1 H 0.4187 0.0884 0.0316 0.029 Uiso 1 1 calc R U . . .
C12 C 0.98137(18) 0.27364(10) -0.01124(18) 0.0203(4) Uani 1 1 d . . . . .
H2 H 1.0296 0.2845 -0.0660 0.024 Uiso 1 1 calc R U . . .
C13 C 0.96975(18) 0.31382(10) 0.07504(18) 0.0193(4) Uani 1 1 d . . . . .
H16 H 1.0103 0.3522 0.0795 0.023 Uiso 1 1 calc R U . . .
C14 C 0.89920(18) 0.29851(10) 0.15533(17) 0.0172(4) Uani 1 1 d . . . . .
H28 H 0.8910 0.3266 0.2140 0.021 Uiso 1 1 calc R U . . .
C15 C 0.84028(17) 0.24166(9) 0.14956(16) 0.0145(4) Uani 1 1 d . . . . .
C16 C 0.65651(18) 0.11274(10) 0.16240(18) 0.0195(4) Uani 1 1 d . . . . .
H6 H 0.7246 0.0923 0.1824 0.023 Uiso 1 1 calc R U . . .
C17 C 0.57497(19) 0.08093(11) 0.10186(18) 0.0229(5) Uani 1 1 d . . . . .
H5 H 0.5878 0.0390 0.0787 0.027 Uiso 1 1 calc R U . . .
C18 C 0.70329(17) 0.29120(9) 0.31264(17) 0.0151(4) Uani 1 1 d . . . . .
C19 C 0.65416(18) 0.33876(10) 0.24693(18) 0.0187(4) Uani 1 1 d . . . . .
H11 H 0.6462 0.3331 0.1710 0.022 Uiso 1 1 calc R U . . .
C20 C 0.61737(19) 0.39392(10) 0.29304(18) 0.0225(5) Uani 1 1 d . . . . .
H10 H 0.5820 0.4255 0.2490 0.027 Uiso 1 1 calc R U . . .
C21 C 0.63239(19) 0.40279(10) 0.40376(19) 0.0238(5) Uani 1 1 d . . . . .
H7 H 0.6087 0.4410 0.4352 0.029 Uiso 1 1 calc R U . . .
C22 C 0.68144(18) 0.35645(10) 0.46826(18) 0.0210(5) Uani 1 1 d . . . . .
H9 H 0.6915 0.3629 0.5439 0.025 Uiso 1 1 calc R U . . .
C23 C 0.71623(17) 0.30039(10) 0.42315(18) 0.0168(4) Uani 1 1 d . . . . .
H8 H 0.7489 0.2683 0.4681 0.020 Uiso 1 1 calc R U . . .
C24 C 0.76750(17) 0.12985(9) 0.41292(16) 0.0157(4) Uani 1 1 d . . . . .
C25 C 0.7807(2) 0.03574(11) 0.5166(2) 0.0250(5) Uani 1 1 d . . . . .
H13 H 0.7181 0.0508 0.5561 0.038 Uiso 1 1 calc R U . . .
H12 H 0.8333 0.0134 0.5663 0.038 Uiso 1 1 calc R U . . .
H14 H 0.7537 0.0070 0.4591 0.038 Uiso 1 1 calc R U . . .
C26 C 1.01852(17) 0.22402(9) 0.35933(16) 0.0147(4) Uani 1 1 d . . . . .
H15 H 0.9945 0.2659 0.3723 0.018 Uiso 1 1 calc R U . . .
C27 C 1.13738(17) 0.20720(9) 0.33990(17) 0.0150(4) Uani 1 1 d . . . . .
H22 H 1.1818 0.2045 0.4103 0.018 Uiso 1 1 calc R U . . .
C28 C 1.06290(17) 0.08850(9) 0.45367(18) 0.0155(4) Uani 1 1 d . . . . .
C29 C 0.96648(17) 0.06264(10) 0.28540(17) 0.0168(4) Uani 1 1 d . . . . .
C30 C 1.31867(18) 0.10780(10) 0.35803(18) 0.0207(5) Uani 1 1 d . . . . .
H21 H 1.3212 0.1428 0.4060 0.025 Uiso 1 1 calc R U . . .
C31 C 1.31118(18) 0.00527(10) 0.21736(18) 0.0194(4) Uani 1 1 d . . . . .
H19 H 1.3093 -0.0298 0.1696 0.023 Uiso 1 1 calc R U . . .
C32 C 1.22235(17) 0.04644(9) 0.21924(17) 0.0167(4) Uani 1 1 d . . . . .
H20 H 1.1588 0.0396 0.1719 0.020 Uiso 1 1 calc R U . . .
C33 C 1.19209(17) 0.25298(10) 0.26542(18) 0.0178(4) Uani 1 1 d . . . . .
C34 C 1.2494(2) 0.35799(10) 0.2437(2) 0.0322(6) Uani 1 1 d . . . . .
H23 H 1.3279 0.3477 0.2379 0.048 Uiso 1 1 calc R U . . .
H25 H 1.2431 0.3994 0.2781 0.048 Uiso 1 1 calc R U . . .
H24 H 1.2119 0.3591 0.1716 0.048 Uiso 1 1 calc R U . . .
C35 C 0.85224(18) 0.20123(10) 0.06272(17) 0.0197(5) Uani 1 1 d . . . . .
H27 H 0.8125 0.1625 0.0583 0.024 Uiso 1 1 calc R U . . .
C36 C 0.92245(19) 0.21751(11) -0.01768(19) 0.0235(5) Uani 1 1 d . . . . .
H26 H 0.9300 0.1900 -0.0772 0.028 Uiso 1 1 calc R U . . .
N1 N 1.10130(16) 0.06835(9) 0.53258(15) 0.0234(4) Uani 1 1 d . . . . .
N2 N 1.49864(16) -0.02587(9) 0.28368(17) 0.0247(4) Uani 1 1 d . . . . .
N3 N 0.92333(16) 0.02306(9) 0.23717(17) 0.0269(4) Uani 1 1 d . . . . .
O1 O 0.66692(12) 0.12875(7) 0.41734(13) 0.0210(3) Uani 1 1 d . . . . .
O2 O 0.83538(12) 0.08874(7) 0.47008(12) 0.0196(3) Uani 1 1 d . . . . .
O3 O 1.49990(16) -0.06339(9) 0.20902(18) 0.0440(5) Uani 1 1 d . . . . .
O4 O 1.57212(14) -0.02153(9) 0.35455(16) 0.0375(5) Uani 1 1 d . . . . .
O5 O 1.19817(13) 0.31040(7) 0.30844(13) 0.0245(4) Uani 1 1 d . . . . .
O6 O 1.22608(14) 0.23913(7) 0.17954(13) 0.0278(4) Uani 1 1 d . . . . .
P1 P 0.75440(4) 0.21857(2) 0.25780(4) 0.01285(11) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C31 1.379(3) . ?
C1 C2 1.380(3) . ?
C1 N2 1.473(3) . ?
C2 C30 1.394(3) . ?
C2 H18 0.9500 . ?
C3 C30 1.390(3) . ?
C3 C32 1.399(3) . ?
C3 C4 1.513(3) . ?
C4 C27 1.538(3) . ?
C4 C5 1.574(3) . ?
C4 H17 1.0000 . ?
C5 C29 1.477(3) . ?
C5 C28 1.478(3) . ?
C5 C6 1.559(3) . ?
C6 C26 1.336(3) . ?
C6 C7 1.455(3) . ?
C7 C24 1.431(3) . ?
C7 P1 1.734(2) . ?
C8 C9 1.392(3) . ?
C8 C16 1.398(3) . ?
C8 P1 1.811(2) . ?
C9 C10 1.386(3) . ?
C9 H3 0.9500 . ?
C10 C11 1.378(3) . ?
C10 H4 0.9500 . ?
C11 C17 1.390(3) . ?
C11 H1 0.9500 . ?
C12 C13 1.382(3) . ?
C12 C36 1.386(3) . ?
C12 H2 0.9500 . ?
C13 C14 1.389(3) . ?
C13 H16 0.9500 . ?
C14 C15 1.399(3) . ?
C14 H28 0.9500 . ?
C15 C35 1.392(3) . ?
C15 P1 1.815(2) . ?
C16 C17 1.379(3) . ?
C16 H6 0.9500 . ?
C17 H5 0.9500 . ?
C18 C23 1.386(3) . ?
C18 C19 1.406(3) . ?
C18 P1 1.807(2) . ?
C19 C20 1.387(3) . ?
C19 H11 0.9500 . ?
C20 C21 1.389(3) . ?
C20 H10 0.9500 . ?
C21 C22 1.379(3) . ?
C21 H7 0.9500 . ?
C22 C23 1.389(3) . ?
C22 H9 0.9500 . ?
C23 H8 0.9500 . ?
C24 O1 1.220(2) . ?
C24 O2 1.366(2) . ?
C25 O2 1.441(3) . ?
C25 H13 0.9800 . ?
C25 H12 0.9800 . ?
C25 H14 0.9800 . ?
C26 C27 1.514(3) . ?
C26 H15 0.9500 . ?
C27 C33 1.519(3) . ?
C27 H22 1.0000 . ?
C28 N1 1.142(3) . ?
C29 N3 1.139(3) . ?
C30 H21 0.9500 . ?
C31 C32 1.385(3) . ?
C31 H19 0.9500 . ?
C32 H20 0.9500 . ?
C33 O6 1.202(3) . ?
C33 O5 1.329(3) . ?
C34 O5 1.451(3) . ?
C34 H23 0.9800 . ?
C34 H25 0.9800 . ?
C34 H24 0.9800 . ?
C35 C36 1.392(3) . ?
C35 H27 0.9500 . ?
C36 H26 0.9500 . ?
N2 O4 1.216(3) . ?
N2 O3 1.222(3) . ?

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
C31 C1 C2 123.01(19) . . ?
C31 C1 N2 118.73(19) . . ?
C2 C1 N2 118.23(19) . . ?
C1 C2 C30 118.0(2) . . ?
C1 C2 H18 121.0 . . ?
C30 C2 H18 121.0 . . ?
C30 C3 C32 119.03(19) . . ?
C30 C3 C4 122.17(18) . . ?
C32 C3 C4 118.80(18) . . ?
C3 C4 C27 119.48(17) . . ?
C3 C4 C5 114.73(16) . . ?
C27 C4 C5 101.77(15) . . ?
C3 C4 H17 106.7 . . ?
C27 C4 H17 106.7 . . ?
C5 C4 H17 106.7 . . ?
C29 C5 C28 108.23(17) . . ?
C29 C5 C6 113.18(17) . . ?
C28 C5 C6 112.77(17) . . ?
C29 C5 C4 112.54(16) . . ?
C28 C5 C4 108.96(16) . . ?
C6 C5 C4 101.04(15) . . ?
C26 C6 C7 129.47(18) . . ?
C26 C6 C5 107.60(17) . . ?
C7 C6 C5 122.63(17) . . ?
C24 C7 C6 123.56(18) . . ?
C24 C7 P1 116.04(15) . . ?
C6 C7 P1 120.24(15) . . ?
C9 C8 C16 119.35(19) . . ?
C9 C8 P1 121.82(16) . . ?
C16 C8 P1 118.64(16) . . ?
C10 C9 C8 119.9(2) . . ?
C10 C9 H3 120.0 . . ?
C8 C9 H3 120.0 . . ?
C11 C10 C9 120.5(2) . . ?
C11 C10 H4 119.8 . . ?
C9 C10 H4 119.8 . . ?
C10 C11 C17 119.8(2) . . ?
C10 C11 H1 120.1 . . ?
C17 C11 H1 120.1 . . ?
C13 C12 C36 119.8(2) . . ?
C13 C12 H2 120.1 . . ?
C36 C12 H2 120.1 . . ?
C12 C13 C14 120.5(2) . . ?
C12 C13 H16 119.7 . . ?
C14 C13 H16 119.7 . . ?
C13 C14 C15 119.8(2) . . ?
C13 C14 H28 120.1 . . ?
C15 C14 H28 120.1 . . ?
C35 C15 C14 119.57(19) . . ?
C35 C15 P1 119.92(16) . . ?
C14 C15 P1 120.42(15) . . ?
C17 C16 C8 120.1(2) . . ?
C17 C16 H6 119.9 . . ?
C8 C16 H6 119.9 . . ?
C16 C17 C11 120.2(2) . . ?
C16 C17 H5 119.9 . . ?
C11 C17 H5 119.9 . . ?
C23 C18 C19 119.51(18) . . ?
C23 C18 P1 118.19(15) . . ?
C19 C18 P1 122.28(16) . . ?
C20 C19 C18 120.0(2) . . ?
C20 C19 H11 120.0 . . ?
C18 C19 H11 120.0 . . ?
C19 C20 C21 119.8(2) . . ?
C19 C20 H10 120.1 . . ?
C21 C20 H10 120.1 . . ?
C22 C21 C20 120.3(2) . . ?
C22 C21 H7 119.8 . . ?
C20 C21 H7 119.8 . . ?
C21 C22 C23 120.3(2) . . ?
C21 C22 H9 119.8 . . ?
C23 C22 H9 119.8 . . ?
C18 C23 C22 120.1(2) . . ?
C18 C23 H8 120.0 . . ?
C22 C23 H8 120.0 . . ?
O1 C24 O2 122.21(18) . . ?
O1 C24 C7 126.70(19) . . ?
O2 C24 C7 111.08(17) . . ?
O2 C25 H13 109.5 . . ?
O2 C25 H12 109.5 . . ?
H13 C25 H12 109.5 . . ?
O2 C25 H14 109.5 . . ?
H13 C25 H14 109.5 . . ?
H12 C25 H14 109.5 . . ?
C6 C26 C27 113.34(17) . . ?
C6 C26 H15 123.3 . . ?
C27 C26 H15 123.3 . . ?
C26 C27 C33 113.51(16) . . ?
C26 C27 C4 102.19(16) . . ?
C33 C27 C4 111.44(17) . . ?
C26 C27 H22 109.8 . . ?
C33 C27 H22 109.8 . . ?
C4 C27 H22 109.8 . . ?
N1 C28 C5 174.7(2) . . ?
N3 C29 C5 179.4(2) . . ?
C3 C30 C2 120.9(2) . . ?
C3 C30 H21 119.6 . . ?
C2 C30 H21 119.6 . . ?
C1 C31 C32 118.13(19) . . ?
C1 C31 H19 120.9 . . ?
C32 C31 H19 120.9 . . ?
C31 C32 C3 121.0(2) . . ?
C31 C32 H20 119.5 . . ?
C3 C32 H20 119.5 . . ?
O6 C33 O5 124.5(2) . . ?
O6 C33 C27 124.68(19) . . ?
O5 C33 C27 110.82(18) . . ?
O5 C34 H23 109.5 . . ?
O5 C34 H25 109.5 . . ?
H23 C34 H25 109.5 . . ?
O5 C34 H24 109.5 . . ?
H23 C34 H24 109.5 . . ?
H25 C34 H24 109.5 . . ?
C15 C35 C36 120.0(2) . . ?
C15 C35 H27 120.0 . . ?
C36 C35 H27 120.0 . . ?
C12 C36 C35 120.3(2) . . ?
C12 C36 H26 119.8 . . ?
C35 C36 H26 119.8 . . ?
O4 N2 O3 123.82(19) . . ?
O4 N2 C1 118.59(19) . . ?
O3 N2 C1 117.6(2) . . ?
C24 O2 C25 115.46(17) . . ?
C33 O5 C34 115.39(18) . . ?
C7 P1 C18 114.31(10) . . ?
C7 P1 C8 111.23(10) . . ?
C18 P1 C8 109.03(9) . . ?
C7 P1 C15 110.02(10) . . ?
C18 P1 C15 105.87(9) . . ?
C8 P1 C15 105.93(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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C31 C1 C2 C30 0.9(3) . . . . ?
N2 C1 C2 C30 178.7(2) . . . . ?
C30 C3 C4 C27 17.4(3) . . . . ?
C32 C3 C4 C27 -162.45(18) . . . . ?
C30 C3 C4 C5 -103.9(2) . . . . ?
C32 C3 C4 C5 76.3(2) . . . . ?
C3 C4 C5 C29 -72.1(2) . . . . ?
C27 C4 C5 C29 157.37(16) . . . . ?
C3 C4 C5 C28 47.9(2) . . . . ?
C27 C4 C5 C28 -82.59(19) . . . . ?
C3 C4 C5 C6 166.85(16) . . . . ?
C27 C4 C5 C6 36.35(18) . . . . ?
C29 C5 C6 C26 -147.91(18) . . . . ?
C28 C5 C6 C26 88.8(2) . . . . ?
C4 C5 C6 C26 -27.3(2) . . . . ?
C29 C5 C6 C7 26.4(3) . . . . ?
C28 C5 C6 C7 -96.9(2) . . . . ?
C4 C5 C6 C7 146.93(19) . . . . ?
C26 C6 C7 C24 -137.3(2) . . . . ?
C5 C6 C7 C24 49.7(3) . . . . ?
C26 C6 C7 P1 47.4(3) . . . . ?
C5 C6 C7 P1 -125.55(18) . . . . ?
C16 C8 C9 C10 -2.1(3) . . . . ?
P1 C8 C9 C10 172.85(17) . . . . ?
C8 C9 C10 C11 -0.9(3) . . . . ?
C9 C10 C11 C17 2.6(4) . . . . ?
C36 C12 C13 C14 -0.2(3) . . . . ?
C12 C13 C14 C15 0.7(3) . . . . ?
C13 C14 C15 C35 -0.6(3) . . . . ?
C13 C14 C15 P1 176.17(16) . . . . ?
C9 C8 C16 C17 3.3(3) . . . . ?
P1 C8 C16 C17 -171.78(17) . . . . ?
C8 C16 C17 C11 -1.6(3) . . . . ?
C10 C11 C17 C16 -1.4(3) . . . . ?
C23 C18 C19 C20 -1.1(3) . . . . ?
P1 C18 C19 C20 -179.30(17) . . . . ?
C18 C19 C20 C21 2.0(3) . . . . ?
C19 C20 C21 C22 -1.5(3) . . . . ?
C20 C21 C22 C23 -0.1(3) . . . . ?
C19 C18 C23 C22 -0.4(3) . . . . ?
P1 C18 C23 C22 177.87(16) . . . . ?
C21 C22 C23 C18 1.0(3) . . . . ?
C6 C7 C24 O1 174.5(2) . . . . ?
P1 C7 C24 O1 -10.0(3) . . . . ?
C6 C7 C24 O2 -5.4(3) . . . . ?
P1 C7 C24 O2 170.11(14) . . . . ?
C7 C6 C26 C27 -166.9(2) . . . . ?
C5 C6 C26 C27 6.8(2) . . . . ?
C6 C26 C27 C33 137.33(19) . . . . ?
C6 C26 C27 C4 17.2(2) . . . . ?
C3 C4 C27 C26 -160.19(17) . . . . ?
C5 C4 C27 C26 -32.70(19) . . . . ?
C3 C4 C27 C33 78.3(2) . . . . ?
C5 C4 C27 C33 -154.24(16) . . . . ?
C32 C3 C30 C2 -0.3(3) . . . . ?
C4 C3 C30 C2 179.9(2) . . . . ?
C1 C2 C30 C3 -0.4(3) . . . . ?
C2 C1 C31 C32 -0.6(3) . . . . ?
N2 C1 C31 C32 -178.40(19) . . . . ?
C1 C31 C32 C3 -0.2(3) . . . . ?
C30 C3 C32 C31 0.6(3) . . . . ?
C4 C3 C32 C31 -179.58(19) . . . . ?
C26 C27 C33 O6 -117.7(2) . . . . ?
C4 C27 C33 O6 -3.0(3) . . . . ?
C26 C27 C33 O5 62.8(2) . . . . ?
C4 C27 C33 O5 177.55(17) . . . . ?
C14 C15 C35 C36 0.0(3) . . . . ?
P1 C15 C35 C36 -176.81(17) . . . . ?
C13 C12 C36 C35 -0.4(3) . . . . ?
C15 C35 C36 C12 0.6(3) . . . . ?
C31 C1 N2 O4 -169.7(2) . . . . ?
C2 C1 N2 O4 12.3(3) . . . . ?
C31 C1 N2 O3 10.6(3) . . . . ?
C2 C1 N2 O3 -167.3(2) . . . . ?
O1 C24 O2 C25 13.1(3) . . . . ?
C7 C24 O2 C25 -166.96(18) . . . . ?
O6 C33 O5 C34 0.4(3) . . . . ?
C27 C33 O5 C34 179.90(18) . . . . ?
C24 C7 P1 C18 86.12(17) . . . . ?
C6 C7 P1 C18 -98.23(17) . . . . ?
C24 C7 P1 C8 -37.89(18) . . . . ?
C6 C7 P1 C8 137.75(16) . . . . ?
C24 C7 P1 C15 -154.94(15) . . . . ?
C6 C7 P1 C15 20.70(19) . . . . ?
C23 C18 P1 C7 -7.5(2) . . . . ?
C19 C18 P1 C7 170.68(17) . . . . ?
C23 C18 P1 C8 117.63(17) . . . . ?
C19 C18 P1 C8 -64.1(2) . . . . ?
C23 C18 P1 C15 -128.80(17) . . . . ?
C19 C18 P1 C15 49.4(2) . . . . ?
C9 C8 P1 C7 142.55(18) . . . . ?
C16 C8 P1 C7 -42.50(19) . . . . ?
C9 C8 P1 C18 15.6(2) . . . . ?
C16 C8 P1 C18 -169.45(16) . . . . ?
C9 C8 P1 C15 -97.93(18) . . . . ?
C16 C8 P1 C15 77.02(18) . . . . ?
C35 C15 P1 C7 84.32(18) . . . . ?
C14 C15 P1 C7 -92.42(18) . . . . ?
C35 C15 P1 C18 -151.69(17) . . . . ?
C14 C15 P1 C18 31.57(19) . . . . ?
C35 C15 P1 C8 -35.99(19) . . . . ?
C14 C15 P1 C8 147.27(17) . . . . ?

_refine_diff_density_max         0.216
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.034

_shelxl_version_number           2014/6

####################################################################### 
# 
# 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_publication_text
_database_code_depnum_ccdc_archive 'CCDC 1051024'
_audit_update_record             
;
2015-02-24 deposited with the CCDC.
2016-01-07 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C36 H28 N3 O6 P'
_chemical_formula_weight         629.58

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.4651(7)
_cell_length_b                   27.3604(18)
_cell_length_c                   11.6914(9)
_cell_angle_alpha                90
_cell_angle_beta                 112.634(2)
_cell_angle_gamma                90
_cell_volume                     3089.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5222
_cell_measurement_theta_min      2.5813
_cell_measurement_theta_max      25.8201

_exptl_crystal_description       Tabullar
_exptl_crystal_colour            Red
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_F_000             1312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.142
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8693
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            25478
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_av_R_equivalents  0.0492
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.489
_diffrn_reflns_theta_max         26.439
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             6308
_reflns_number_gt                4885
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX2 (Bruker AXS, 2010)'
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  SHELXTL
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0978P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6308
_refine_ls_number_parameters     417
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1620
_refine_ls_wR_factor_gt          0.1242
_refine_ls_goodness_of_fit_ref   1.106
_refine_ls_restrained_S_all      1.106
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.88732(5) 0.38945(2) 0.05549(5) 0.01471(16) Uani 1 1 d . . . . .
O1 O 0.29432(17) 0.37220(7) 0.46448(18) 0.0395(5) Uani 1 1 d . . . . .
O2 O 0.82536(16) 0.30821(5) -0.10848(13) 0.0233(4) Uani 1 1 d . . . . .
O3 O 0.76767(15) 0.25299(5) 0.00725(13) 0.0214(3) Uani 1 1 d . . . . .
O4 O 0.35198(17) 0.43625(6) 0.38702(17) 0.0365(4) Uani 1 1 d . . . . .
O5 O 1.03116(17) 0.39503(6) 0.53815(15) 0.0284(4) Uani 1 1 d . . . . .
O6 O 1.01614(16) 0.32987(6) 0.64845(13) 0.0276(4) Uani 1 1 d . . . . .
N1 N 0.37187(19) 0.39398(7) 0.42602(17) 0.0264(5) Uani 1 1 d . . . . .
N2 N 0.8943(2) 0.19007(7) 0.26011(19) 0.0318(5) Uani 1 1 d . . . . .
N3 N 0.53602(19) 0.28561(7) 0.12424(18) 0.0296(5) Uani 1 1 d . . . . .
C1 C 0.8158(2) 0.50764(8) 0.3057(2) 0.0264(5) Uani 1 1 d . . . . .
H1 H 0.7999 0.5325 0.3555 0.032 Uiso 1 1 calc R U . . .
C2 C 0.7046(2) 0.48511(8) 0.2132(2) 0.0242(5) Uani 1 1 d . . . . .
H5 H 0.6125 0.4944 0.2000 0.029 Uiso 1 1 calc R U . . .
C3 C 0.7283(2) 0.44911(8) 0.1399(2) 0.0203(5) Uani 1 1 d . . . . .
H6 H 0.6522 0.4338 0.0767 0.024 Uiso 1 1 calc R U . . .
C4 C 0.8626(2) 0.43522(7) 0.15835(19) 0.0163(4) Uani 1 1 d . . . . .
C5 C 0.8479(2) 0.33139(7) 0.09088(18) 0.0166(4) Uani 1 1 d . . . . .
C6 C 0.8817(2) 0.31839(7) 0.22027(18) 0.0146(4) Uani 1 1 d . . . . .
C7 C 0.80107(19) 0.27887(7) 0.25938(18) 0.0144(4) Uani 1 1 d . . . . .
C8 C 0.8361(2) 0.29042(7) 0.40161(18) 0.0158(4) Uani 1 1 d . . . . .
H16 H 0.8470 0.2590 0.4479 0.019 Uiso 1 1 calc R U . . .
C9 C 0.7217(2) 0.31997(7) 0.41674(17) 0.0156(4) Uani 1 1 d . . . . .
C10 C 0.7022(2) 0.36970(7) 0.38662(19) 0.0181(4) Uani 1 1 d . . . . .
H17 H 0.7674 0.3868 0.3631 0.022 Uiso 1 1 calc R U . . .
C11 C 0.5885(2) 0.39403(8) 0.39094(19) 0.0204(5) Uani 1 1 d . . . . .
H20 H 0.5746 0.4277 0.3700 0.025 Uiso 1 1 calc R U . . .
C12 C 0.4954(2) 0.36871(8) 0.42614(18) 0.0194(5) Uani 1 1 d . . . . .
C13 C 0.5814(2) 0.44808(8) -0.3170(2) 0.0250(5) Uani 1 1 d . . . . .
H2 H 0.5161 0.4627 -0.3897 0.030 Uiso 1 1 calc R U . . .
C14 C 0.7200(2) 0.45925(8) -0.2793(2) 0.0264(5) Uani 1 1 d . . . . .
H28 H 0.7504 0.4803 -0.3284 0.032 Uiso 1 1 calc R U . . .
C15 C 0.8158(2) 0.43993(8) -0.16947(19) 0.0201(5) Uani 1 1 d . . . . .
H27 H 0.9112 0.4478 -0.1436 0.024 Uiso 1 1 calc R U . . .
C16 C 0.7709(2) 0.40898(7) -0.09771(18) 0.0165(4) Uani 1 1 d . . . . .
C17 C 0.9495(2) 0.49367(8) 0.3250(2) 0.0265(5) Uani 1 1 d . . . . .
H4 H 1.0254 0.5090 0.3884 0.032 Uiso 1 1 calc R U . . .
C18 C 0.9737(2) 0.45755(8) 0.2527(2) 0.0219(5) Uani 1 1 d . . . . .
H3 H 1.0659 0.4480 0.2673 0.026 Uiso 1 1 calc R U . . .
C19 C 1.0648(2) 0.39440(7) 0.06814(18) 0.0176(4) Uani 1 1 d . . . . .
C20 C 1.1288(2) 0.43794(8) 0.0569(2) 0.0236(5) Uani 1 1 d . . . . .
H11 H 1.0795 0.4679 0.0441 0.028 Uiso 1 1 calc R U . . .
C21 C 1.2648(2) 0.43740(10) 0.0642(2) 0.0308(6) Uani 1 1 d . . . . .
H10 H 1.3078 0.4669 0.0553 0.037 Uiso 1 1 calc R U . . .
C22 C 1.3367(2) 0.39397(10) 0.0846(2) 0.0333(6) Uani 1 1 d . . . . .
H7 H 1.4289 0.3936 0.0881 0.040 Uiso 1 1 calc R U . . .
C23 C 1.2766(2) 0.35113(10) 0.0999(2) 0.0298(5) Uani 1 1 d . . . . .
H8 H 1.3281 0.3216 0.1162 0.036 Uiso 1 1 calc R U . . .
C24 C 1.1412(2) 0.35105(8) 0.09161(19) 0.0219(5) Uani 1 1 d . . . . .
H9 H 1.0998 0.3213 0.1019 0.026 Uiso 1 1 calc R U . . .
C25 C 0.8082(2) 0.29396(7) -0.00258(18) 0.0167(4) Uani 1 1 d . . . . .
C26 C 0.7592(3) 0.27836(9) -0.2168(2) 0.0297(6) Uani 1 1 d . . . . .
H12 H 0.7765 0.2438 -0.1942 0.045 Uiso 1 1 calc R U . . .
H13 H 0.7967 0.2864 -0.2794 0.045 Uiso 1 1 calc R U . . .
H14 H 0.6592 0.2845 -0.2505 0.045 Uiso 1 1 calc R U . . .
C27 C 0.9798(2) 0.33657(7) 0.32269(18) 0.0161(4) Uani 1 1 d . . . . .
H15 H 1.0440 0.3607 0.3205 0.019 Uiso 1 1 calc R U . . .
C28 C 0.9799(2) 0.31568(8) 0.44068(18) 0.0167(4) Uani 1 1 d . . . . .
H24 H 1.0524 0.2896 0.4687 0.020 Uiso 1 1 calc R U . . .
C29 C 0.8517(2) 0.22872(8) 0.25249(19) 0.0193(5) Uani 1 1 d . . . . .
C30 C 0.6510(2) 0.28161(7) 0.18246(18) 0.0171(4) Uani 1 1 d . . . . .
C31 C 0.5126(2) 0.31992(8) 0.45977(19) 0.0216(5) Uani 1 1 d . . . . .
H18 H 0.4488 0.3034 0.4860 0.026 Uiso 1 1 calc R U . . .
C32 C 0.6269(2) 0.29601(8) 0.45365(19) 0.0197(5) Uani 1 1 d . . . . .
H19 H 0.6405 0.2624 0.4753 0.024 Uiso 1 1 calc R U . . .
C33 C 1.0113(2) 0.35225(8) 0.54491(19) 0.0189(5) Uani 1 1 d . . . . .
C34 C 1.0527(3) 0.36084(10) 0.7564(2) 0.0407(7) Uani 1 1 d . . . . .
H21 H 1.1499 0.3708 0.7829 0.061 Uiso 1 1 calc R U . . .
H23 H 1.0396 0.3428 0.8235 0.061 Uiso 1 1 calc R U . . .
H22 H 0.9936 0.3899 0.7359 0.061 Uiso 1 1 calc R U . . .
C35 C 0.6316(2) 0.39598(8) -0.13895(19) 0.0194(5) Uani 1 1 d . . . . .
H26 H 0.6012 0.3739 -0.0921 0.023 Uiso 1 1 calc R U . . .
C36 C 0.5371(2) 0.41555(8) -0.2492(2) 0.0231(5) Uani 1 1 d . . . . .
H25 H 0.4422 0.4066 -0.2778 0.028 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 C5 1.731(2) . ?
P1 C19 1.810(2) . ?
P1 C16 1.816(2) . ?
P1 C4 1.822(2) . ?
O1 N1 1.223(3) . ?
O2 C25 1.374(2) . ?
O2 C26 1.441(2) . ?
O3 C25 1.220(2) . ?
O4 N1 1.231(2) . ?
O5 C33 1.197(3) . ?
O6 C33 1.340(3) . ?
O6 C34 1.444(3) . ?
N1 C12 1.465(3) . ?
N2 C29 1.138(3) . ?
N3 C30 1.137(3) . ?
C1 C17 1.383(3) . ?
C1 C2 1.391(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.389(3) . ?
C2 H5 0.9500 . ?
C3 C4 1.390(3) . ?
C3 H6 0.9500 . ?
C4 C18 1.398(3) . ?
C5 C25 1.437(3) . ?
C5 C6 1.459(3) . ?
C6 C27 1.338(3) . ?
C6 C7 1.545(3) . ?
C7 C30 1.481(3) . ?
C7 C29 1.484(3) . ?
C7 C8 1.591(3) . ?
C8 C9 1.510(3) . ?
C8 C28 1.556(3) . ?
C8 H16 1.0000 . ?
C9 C32 1.390(3) . ?
C9 C10 1.401(3) . ?
C10 C11 1.381(3) . ?
C10 H17 0.9500 . ?
C11 C12 1.382(3) . ?
C11 H20 0.9500 . ?
C12 C31 1.384(3) . ?
C13 C14 1.378(3) . ?
C13 C36 1.385(3) . ?
C13 H2 0.9500 . ?
C14 C15 1.394(3) . ?
C14 H28 0.9500 . ?
C15 C16 1.395(3) . ?
C15 H27 0.9500 . ?
C16 C35 1.394(3) . ?
C17 C18 1.386(3) . ?
C17 H4 0.9500 . ?
C18 H3 0.9500 . ?
C19 C24 1.397(3) . ?
C19 C20 1.398(3) . ?
C20 C21 1.392(3) . ?
C20 H11 0.9500 . ?
C21 C22 1.378(4) . ?
C21 H10 0.9500 . ?
C22 C23 1.374(4) . ?
C22 H7 0.9500 . ?
C23 C24 1.383(3) . ?
C23 H8 0.9500 . ?
C24 H9 0.9500 . ?
C26 H12 0.9800 . ?
C26 H13 0.9800 . ?
C26 H14 0.9800 . ?
C27 C28 1.493(3) . ?
C27 H15 0.9500 . ?
C28 C33 1.512(3) . ?
C28 H24 1.0000 . ?
C31 C32 1.389(3) . ?
C31 H18 0.9500 . ?
C32 H19 0.9500 . ?
C34 H21 0.9800 . ?
C34 H23 0.9800 . ?
C34 H22 0.9800 . ?
C35 C36 1.395(3) . ?
C35 H26 0.9500 . ?
C36 H25 0.9500 . ?

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
C5 P1 C19 112.34(10) . . ?
C5 P1 C16 112.01(9) . . ?
C19 P1 C16 109.64(9) . . ?
C5 P1 C4 111.45(10) . . ?
C19 P1 C4 107.24(9) . . ?
C16 P1 C4 103.72(9) . . ?
C25 O2 C26 116.49(17) . . ?
C33 O6 C34 115.24(18) . . ?
O1 N1 O4 123.51(19) . . ?
O1 N1 C12 118.65(19) . . ?
O4 N1 C12 117.84(19) . . ?
C17 C1 C2 119.7(2) . . ?
C17 C1 H1 120.2 . . ?
C2 C1 H1 120.2 . . ?
C3 C2 C1 120.0(2) . . ?
C3 C2 H5 120.0 . . ?
C1 C2 H5 120.0 . . ?
C2 C3 C4 120.6(2) . . ?
C2 C3 H6 119.7 . . ?
C4 C3 H6 119.7 . . ?
C3 C4 C18 119.12(19) . . ?
C3 C4 P1 118.51(15) . . ?
C18 C4 P1 122.36(16) . . ?
C25 C5 C6 119.89(17) . . ?
C25 C5 P1 119.87(15) . . ?
C6 C5 P1 119.12(15) . . ?
C27 C6 C5 129.31(19) . . ?
C27 C6 C7 108.29(18) . . ?
C5 C6 C7 122.39(17) . . ?
C30 C7 C29 109.35(16) . . ?
C30 C7 C6 110.92(16) . . ?
C29 C7 C6 112.57(17) . . ?
C30 C7 C8 112.88(16) . . ?
C29 C7 C8 107.27(15) . . ?
C6 C7 C8 103.75(15) . . ?
C9 C8 C28 116.65(17) . . ?
C9 C8 C7 110.76(15) . . ?
C28 C8 C7 101.72(15) . . ?
C9 C8 H16 109.1 . . ?
C28 C8 H16 109.1 . . ?
C7 C8 H16 109.1 . . ?
C32 C9 C10 118.94(19) . . ?
C32 C9 C8 118.49(18) . . ?
C10 C9 C8 122.41(18) . . ?
C11 C10 C9 120.2(2) . . ?
C11 C10 H17 119.9 . . ?
C9 C10 H17 119.9 . . ?
C10 C11 C12 119.1(2) . . ?
C10 C11 H20 120.5 . . ?
C12 C11 H20 120.5 . . ?
C11 C12 C31 122.6(2) . . ?
C11 C12 N1 119.10(19) . . ?
C31 C12 N1 118.32(19) . . ?
C14 C13 C36 120.1(2) . . ?
C14 C13 H2 119.9 . . ?
C36 C13 H2 119.9 . . ?
C13 C14 C15 120.4(2) . . ?
C13 C14 H28 119.8 . . ?
C15 C14 H28 119.8 . . ?
C14 C15 C16 119.7(2) . . ?
C14 C15 H27 120.2 . . ?
C16 C15 H27 120.2 . . ?
C35 C16 C15 119.74(18) . . ?
C35 C16 P1 118.77(16) . . ?
C15 C16 P1 121.25(15) . . ?
C1 C17 C18 120.6(2) . . ?
C1 C17 H4 119.7 . . ?
C18 C17 H4 119.7 . . ?
C17 C18 C4 120.1(2) . . ?
C17 C18 H3 119.9 . . ?
C4 C18 H3 119.9 . . ?
C24 C19 C20 118.9(2) . . ?
C24 C19 P1 116.36(16) . . ?
C20 C19 P1 124.75(16) . . ?
C21 C20 C19 120.0(2) . . ?
C21 C20 H11 120.0 . . ?
C19 C20 H11 120.0 . . ?
C22 C21 C20 119.9(2) . . ?
C22 C21 H10 120.1 . . ?
C20 C21 H10 120.1 . . ?
C23 C22 C21 120.7(2) . . ?
C23 C22 H7 119.6 . . ?
C21 C22 H7 119.6 . . ?
C22 C23 C24 120.0(2) . . ?
C22 C23 H8 120.0 . . ?
C24 C23 H8 120.0 . . ?
C23 C24 C19 120.4(2) . . ?
C23 C24 H9 119.8 . . ?
C19 C24 H9 119.8 . . ?
O3 C25 O2 121.09(18) . . ?
O3 C25 C5 126.34(19) . . ?
O2 C25 C5 112.52(17) . . ?
O2 C26 H12 109.5 . . ?
O2 C26 H13 109.5 . . ?
H12 C26 H13 109.5 . . ?
O2 C26 H14 109.5 . . ?
H12 C26 H14 109.5 . . ?
H13 C26 H14 109.5 . . ?
C6 C27 C28 114.32(18) . . ?
C6 C27 H15 122.8 . . ?
C28 C27 H15 122.8 . . ?
C27 C28 C33 114.44(18) . . ?
C27 C28 C8 104.02(15) . . ?
C33 C28 C8 114.61(17) . . ?
C27 C28 H24 107.8 . . ?
C33 C28 H24 107.8 . . ?
C8 C28 H24 107.8 . . ?
N2 C29 C7 172.9(2) . . ?
N3 C30 C7 177.3(2) . . ?
C12 C31 C32 117.4(2) . . ?
C12 C31 H18 121.3 . . ?
C32 C31 H18 121.3 . . ?
C31 C32 C9 121.7(2) . . ?
C31 C32 H19 119.1 . . ?
C9 C32 H19 119.1 . . ?
O5 C33 O6 124.01(19) . . ?
O5 C33 C28 125.7(2) . . ?
O6 C33 C28 110.28(18) . . ?
O6 C34 H21 109.5 . . ?
O6 C34 H23 109.5 . . ?
H21 C34 H23 109.5 . . ?
O6 C34 H22 109.5 . . ?
H21 C34 H22 109.5 . . ?
H23 C34 H22 109.5 . . ?
C16 C35 C36 119.8(2) . . ?
C16 C35 H26 120.1 . . ?
C36 C35 H26 120.1 . . ?
C13 C36 C35 120.1(2) . . ?
C13 C36 H25 120.0 . . ?
C35 C36 H25 120.0 . . ?

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
C17 C1 C2 C3 -0.6(3) . . . . ?
C1 C2 C3 C4 0.1(3) . . . . ?
C2 C3 C4 C18 0.8(3) . . . . ?
C2 C3 C4 P1 -177.68(16) . . . . ?
C5 P1 C4 C3 -75.41(18) . . . . ?
C19 P1 C4 C3 161.25(16) . . . . ?
C16 P1 C4 C3 45.28(19) . . . . ?
C5 P1 C4 C18 106.18(19) . . . . ?
C19 P1 C4 C18 -17.2(2) . . . . ?
C16 P1 C4 C18 -133.13(18) . . . . ?
C19 P1 C5 C25 -83.80(18) . . . . ?
C16 P1 C5 C25 40.1(2) . . . . ?
C4 P1 C5 C25 155.82(16) . . . . ?
C19 P1 C5 C6 84.12(18) . . . . ?
C16 P1 C5 C6 -151.96(15) . . . . ?
C4 P1 C5 C6 -36.25(19) . . . . ?
C25 C5 C6 C27 141.8(2) . . . . ?
P1 C5 C6 C27 -26.1(3) . . . . ?
C25 C5 C6 C7 -38.6(3) . . . . ?
P1 C5 C6 C7 153.44(15) . . . . ?
C27 C6 C7 C30 140.27(18) . . . . ?
C5 C6 C7 C30 -39.3(2) . . . . ?
C27 C6 C7 C29 -96.8(2) . . . . ?
C5 C6 C7 C29 83.5(2) . . . . ?
C27 C6 C7 C8 18.8(2) . . . . ?
C5 C6 C7 C8 -160.81(17) . . . . ?
C30 C7 C8 C9 -22.3(2) . . . . ?
C29 C7 C8 C9 -142.85(17) . . . . ?
C6 C7 C8 C9 97.81(18) . . . . ?
C30 C7 C8 C28 -146.98(16) . . . . ?
C29 C7 C8 C28 92.50(18) . . . . ?
C6 C7 C8 C28 -26.83(18) . . . . ?
C28 C8 C9 C32 -143.32(19) . . . . ?
C7 C8 C9 C32 101.0(2) . . . . ?
C28 C8 C9 C10 41.3(3) . . . . ?
C7 C8 C9 C10 -74.4(2) . . . . ?
C32 C9 C10 C11 -1.5(3) . . . . ?
C8 C9 C10 C11 173.88(18) . . . . ?
C9 C10 C11 C12 0.4(3) . . . . ?
C10 C11 C12 C31 1.3(3) . . . . ?
C10 C11 C12 N1 -177.59(18) . . . . ?
O1 N1 C12 C11 -175.6(2) . . . . ?
O4 N1 C12 C11 4.3(3) . . . . ?
O1 N1 C12 C31 5.5(3) . . . . ?
O4 N1 C12 C31 -174.60(19) . . . . ?
C36 C13 C14 C15 -3.3(3) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
C14 C15 C16 C35 2.7(3) . . . . ?
C14 C15 C16 P1 -171.69(17) . . . . ?
C5 P1 C16 C35 37.44(19) . . . . ?
C19 P1 C16 C35 162.86(16) . . . . ?
C4 P1 C16 C35 -82.87(17) . . . . ?
C5 P1 C16 C15 -148.12(17) . . . . ?
C19 P1 C16 C15 -22.70(19) . . . . ?
C4 P1 C16 C15 91.57(18) . . . . ?
C2 C1 C17 C18 0.2(4) . . . . ?
C1 C17 C18 C4 0.7(3) . . . . ?
C3 C4 C18 C17 -1.2(3) . . . . ?
P1 C4 C18 C17 177.22(17) . . . . ?
C5 P1 C19 C24 6.16(19) . . . . ?
C16 P1 C19 C24 -119.07(16) . . . . ?
C4 P1 C19 C24 128.94(16) . . . . ?
C5 P1 C19 C20 -173.45(17) . . . . ?
C16 P1 C19 C20 61.3(2) . . . . ?
C4 P1 C19 C20 -50.7(2) . . . . ?
C24 C19 C20 C21 2.5(3) . . . . ?
P1 C19 C20 C21 -177.93(17) . . . . ?
C19 C20 C21 C22 -1.0(3) . . . . ?
C20 C21 C22 C23 -1.1(4) . . . . ?
C21 C22 C23 C24 1.8(4) . . . . ?
C22 C23 C24 C19 -0.2(3) . . . . ?
C20 C19 C24 C23 -1.9(3) . . . . ?
P1 C19 C24 C23 178.51(16) . . . . ?
C26 O2 C25 O3 16.3(3) . . . . ?
C26 O2 C25 C5 -165.90(18) . . . . ?
C6 C5 C25 O3 18.3(3) . . . . ?
P1 C5 C25 O3 -173.84(16) . . . . ?
C6 C5 C25 O2 -159.31(17) . . . . ?
P1 C5 C25 O2 8.5(2) . . . . ?
C5 C6 C27 C28 177.47(19) . . . . ?
C7 C6 C27 C28 -2.1(2) . . . . ?
C6 C27 C28 C33 -141.70(19) . . . . ?
C6 C27 C28 C8 -15.9(2) . . . . ?
C9 C8 C28 C27 -95.03(19) . . . . ?
C7 C8 C28 C27 25.58(19) . . . . ?
C9 C8 C28 C33 30.7(2) . . . . ?
C7 C8 C28 C33 151.27(16) . . . . ?
C11 C12 C31 C32 -1.9(3) . . . . ?
N1 C12 C31 C32 177.01(18) . . . . ?
C12 C31 C32 C9 0.8(3) . . . . ?
C10 C9 C32 C31 0.9(3) . . . . ?
C8 C9 C32 C31 -174.68(18) . . . . ?
C34 O6 C33 O5 -2.2(3) . . . . ?
C34 O6 C33 C28 176.87(18) . . . . ?
C27 C28 C33 O5 2.2(3) . . . . ?
C8 C28 C33 O5 -117.8(2) . . . . ?
C27 C28 C33 O6 -176.86(17) . . . . ?
C8 C28 C33 O6 63.1(2) . . . . ?
C15 C16 C35 C36 -2.6(3) . . . . ?
P1 C16 C35 C36 171.95(16) . . . . ?
C14 C13 C36 C35 3.4(3) . . . . ?
C16 C35 C36 C13 -0.5(3) . . . . ?

_refine_diff_density_max         0.417
_refine_diff_density_min         -0.639
_refine_diff_density_rms         0.144

_shelxl_version_number           2014/6

