# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1563420'
_audit_update_record             
;
2017-07-20 deposited with the CCDC.
2017-09-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H35 N O1.50 P'
_chemical_formula_weight         428.53

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c

loop_
_symmetry_equiv_pos_as_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'
'-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                   10.5217(13)
_cell_length_b                   14.8118(18)
_cell_length_c                   29.451(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.420(3)
_cell_angle_gamma                90.00
_cell_volume                     4576.2(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    128(2)
_cell_measurement_reflns_used    5926
_cell_measurement_theta_min      3.1
_cell_measurement_theta_max      27.5

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.244
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1848
_exptl_absorpt_coefficient_mu    0.142
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9722
_exptl_absorpt_correction_T_max  0.9832
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      128(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  multilayer
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 5.814
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            22998
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_av_sigmaI/netI    0.0241
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         3.06
_diffrn_reflns_theta_max         27.49
_reflns_number_total             5190
_reflns_number_gt                4430
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42'
_computing_data_reduction        'CrystalClear-SM Expert 2.1 b42'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'CrystalStructure 4.1'
_computing_publication_material  'CrystalStructure 4.1 (Rigaku, 2014)'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0486P)²+3.2389P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5190
_refine_ls_number_parameters     277
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0968
_refine_ls_wR_factor_gt          0.0934
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.002
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.75737(3) 1.03167(2) 0.664974(10) 0.01619(9) Uani 1 1 d . . .
O1 O 0.84185(10) 1.10679(7) 0.68326(3) 0.0278(2) Uani 1 1 d . . .
N1 N 0.94697(10) 0.98265(7) 0.60645(4) 0.0174(2) Uani 1 1 d . . .
C1 C 0.96132(11) 0.93847(8) 0.56611(4) 0.0166(2) Uani 1 1 d . . .
C2 C 1.07012(12) 0.92801(9) 0.54200(4) 0.0206(3) Uani 1 1 d . . .
H2 H 1.1499 0.9530 0.5528 0.025 Uiso 1 1 calc R . .
C3 C 1.05641(13) 0.87987(9) 0.50193(5) 0.0229(3) Uani 1 1 d . . .
H3 H 1.1286 0.8713 0.4849 0.028 Uiso 1 1 calc R . .
C4 C 0.93855(13) 0.84307(9) 0.48546(4) 0.0213(3) Uani 1 1 d . . .
H4 H 0.9324 0.8108 0.4575 0.026 Uiso 1 1 calc R . .
C5 C 0.83164(12) 0.85328(8) 0.50939(4) 0.0182(2) Uani 1 1 d . . .
H5 H 0.7520 0.8287 0.4981 0.022 Uiso 1 1 calc R . .
C6 C 0.84335(11) 0.90066(8) 0.55068(4) 0.0154(2) Uani 1 1 d . . .
C7 C 0.75595(11) 0.92052(8) 0.58425(4) 0.0152(2) Uani 1 1 d . . .
C8 C 0.62357(11) 0.88595(8) 0.58175(4) 0.0154(2) Uani 1 1 d . . .
C9 C 0.58066(12) 0.82783(8) 0.61473(4) 0.0183(2) Uani 1 1 d . . .
H9 H 0.6376 0.8095 0.6396 0.022 Uiso 1 1 calc R . .
C10 C 0.45554(13) 0.79644(9) 0.61159(5) 0.0221(3) Uani 1 1 d . . .
H10 H 0.4272 0.7578 0.6345 0.027 Uiso 1 1 calc R . .
C11 C 0.37245(12) 0.82160(9) 0.57503(5) 0.0250(3) Uani 1 1 d . . .
H11 H 0.2868 0.8008 0.5730 0.030 Uiso 1 1 calc R . .
C12 C 0.41460(12) 0.87715(9) 0.54142(5) 0.0238(3) Uani 1 1 d . . .
H12 H 0.3580 0.8937 0.5161 0.029 Uiso 1 1 calc R . .
C13 C 0.53918(12) 0.90872(8) 0.54464(4) 0.0187(3) Uani 1 1 d . . .
H13 H 0.5673 0.9463 0.5213 0.022 Uiso 1 1 calc R . .
C14 C 1.05047(13) 1.03236(10) 0.63092(5) 0.0246(3) Uani 1 1 d . . .
H14A H 1.1260 0.9936 0.6351 0.037 Uiso 1 1 calc R . .
H14B H 1.0243 1.0508 0.6608 0.037 Uiso 1 1 calc R . .
H14C H 1.0707 1.0860 0.6134 0.037 Uiso 1 1 calc R . .
C15 C 0.82111(11) 0.97252(8) 0.61761(4) 0.0159(2) Uani 1 1 d . . .
C16 C 0.72913(12) 0.94594(8) 0.70759(4) 0.0177(2) Uani 1 1 d . . .
H16 H 0.6462 0.9157 0.6983 0.021 Uiso 1 1 calc R . .
C17 C 0.71885(13) 0.98730(9) 0.75511(4) 0.0217(3) Uani 1 1 d . . .
H17A H 0.8010 1.0157 0.7658 0.026 Uiso 1 1 calc R . .
H17B H 0.6523 1.0347 0.7535 0.026 Uiso 1 1 calc R . .
C18 C 0.68513(13) 0.91395(10) 0.78868(4) 0.0242(3) Uani 1 1 d . . .
H18A H 0.6793 0.9412 0.8192 0.029 Uiso 1 1 calc R . .
H18B H 0.6007 0.8882 0.7788 0.029 Uiso 1 1 calc R . .
C19 C 0.78433(15) 0.83855(10) 0.79195(5) 0.0290(3) Uani 1 1 d . . .
H19A H 0.7560 0.7899 0.8119 0.035 Uiso 1 1 calc R . .
H19B H 0.8663 0.8625 0.8057 0.035 Uiso 1 1 calc R . .
C20 C 0.80361(16) 0.79988(10) 0.74486(5) 0.0321(3) Uani 1 1 d . . .
H20A H 0.8745 0.7558 0.7475 0.039 Uiso 1 1 calc R . .
H20B H 0.7254 0.7674 0.7333 0.039 Uiso 1 1 calc R . .
C21 C 0.83350(14) 0.87325(10) 0.71083(4) 0.0247(3) Uani 1 1 d . . .
H21A H 0.8403 0.8458 0.6805 0.030 Uiso 1 1 calc R . .
H21B H 0.9165 0.9014 0.7205 0.030 Uiso 1 1 calc R . .
C22 C 0.60340(12) 1.07024(8) 0.64000(4) 0.0167(2) Uani 1 1 d . . .
H22 H 0.5588 1.0167 0.6255 0.020 Uiso 1 1 calc R . .
C23 C 0.62169(13) 1.13921(9) 0.60198(4) 0.0242(3) Uani 1 1 d . . .
H23A H 0.6656 1.1934 0.6151 0.029 Uiso 1 1 calc R . .
H23B H 0.6759 1.1125 0.5795 0.029 Uiso 1 1 calc R . .
C24 C 0.49344(14) 1.16664(10) 0.57821(5) 0.0289(3) Uani 1 1 d . . .
H24A H 0.5071 1.2131 0.5549 0.035 Uiso 1 1 calc R . .
H24B H 0.4534 1.1135 0.5625 0.035 Uiso 1 1 calc R . .
C25 C 0.40456(14) 1.20383(10) 0.61205(5) 0.0284(3) Uani 1 1 d . . .
H25A H 0.4397 1.2611 0.6250 0.034 Uiso 1 1 calc R . .
H25B H 0.3203 1.2169 0.5961 0.034 Uiso 1 1 calc R . .
C26 C 0.38828(13) 1.13695(9) 0.65038(5) 0.0243(3) Uani 1 1 d . . .
H26A H 0.3439 1.0825 0.6378 0.029 Uiso 1 1 calc R . .
H26B H 0.3345 1.1645 0.6728 0.029 Uiso 1 1 calc R . .
C27 C 0.51632(12) 1.10952(9) 0.67440(4) 0.0196(3) Uani 1 1 d . . .
H27A H 0.5025 1.0640 0.6981 0.023 Uiso 1 1 calc R . .
H27B H 0.5576 1.1629 0.6895 0.023 Uiso 1 1 calc R . .
O2 O 0.5000 0.70016(16) 0.7500 0.1147(13) Uani 1 2 d SD . .
H2A H 0.4832 0.6613 0.7267 0.138 Uiso 0.50 1 d PRD . .
H2A' H 0.5547 0.6766 0.7722 0.138 Uiso 0.50 1 d PRD . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.4981(10) . ?
P1 C15 1.8186(12) . ?
P1 C22 1.8189(13) . ?
P1 C16 1.8257(13) . ?
N1 C1 1.3748(16) . ?
N1 C15 1.3969(15) . ?
N1 C14 1.4583(16) . ?
C1 C2 1.4014(16) . ?
C1 C6 1.4049(17) . ?
C2 C3 1.3768(19) . ?
C2 H2 0.9500 . ?
C3 C4 1.406(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.3810(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.4013(17) . ?
C5 H5 0.9500 . ?
C6 C7 1.4316(16) . ?
C7 C15 1.3874(17) . ?
C7 C8 1.4805(16) . ?
C8 C13 1.3953(17) . ?
C8 C9 1.3987(17) . ?
C9 C10 1.3925(18) . ?
C9 H9 0.9500 . ?
C10 C11 1.385(2) . ?
C10 H10 0.9500 . ?
C11 C12 1.3861(19) . ?
C11 H11 0.9500 . ?
C12 C13 1.3881(18) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C16 C21 1.5356(17) . ?
C16 C17 1.5391(16) . ?
C16 H16 1.0000 . ?
C17 C18 1.5291(18) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.5266(19) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 C20 1.5284(19) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 C21 1.5273(19) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C27 1.5322(16) . ?
C22 C23 1.5387(17) . ?
C22 H22 1.0000 . ?
C23 C24 1.527(2) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 C25 1.5215(19) . ?
C24 H24A 0.9900 . ?
C24 H24B 0.9900 . ?
C25 C26 1.5214(19) . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C26 C27 1.5277(18) . ?
C26 H26A 0.9900 . ?
C26 H26B 0.9900 . ?
C27 H27A 0.9900 . ?
C27 H27B 0.9900 . ?
O2 H2A 0.9022 . ?
O2 H2A' 0.9073 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C15 112.95(6) . . ?
O1 P1 C22 113.42(6) . . ?
C15 P1 C22 102.16(6) . . ?
O1 P1 C16 113.13(6) . . ?
C15 P1 C16 106.34(6) . . ?
C22 P1 C16 108.02(6) . . ?
C1 N1 C15 108.76(10) . . ?
C1 N1 C14 122.67(10) . . ?
C15 N1 C14 128.55(11) . . ?
N1 C1 C2 129.71(12) . . ?
N1 C1 C6 108.42(10) . . ?
C2 C1 C6 121.87(12) . . ?
C3 C2 C1 117.11(12) . . ?
C3 C2 H2 121.4 . . ?
C1 C2 H2 121.4 . . ?
C2 C3 C4 121.86(12) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 120.85(12) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 118.50(12) . . ?
C4 C5 H5 120.7 . . ?
C6 C5 H5 120.7 . . ?
C5 C6 C1 119.78(11) . . ?
C5 C6 C7 133.16(12) . . ?
C1 C6 C7 107.06(11) . . ?
C15 C7 C6 107.13(10) . . ?
C15 C7 C8 129.70(11) . . ?
C6 C7 C8 123.13(11) . . ?
C13 C8 C9 118.21(11) . . ?
C13 C8 C7 119.66(11) . . ?
C9 C8 C7 122.09(11) . . ?
C10 C9 C8 120.90(12) . . ?
C10 C9 H9 119.5 . . ?
C8 C9 H9 119.5 . . ?
C11 C10 C9 119.92(12) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 119.84(12) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C11 C12 C13 120.24(13) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C8 120.84(12) . . ?
C12 C13 H13 119.6 . . ?
C8 C13 H13 119.6 . . ?
N1 C14 H14A 109.5 . . ?
N1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
N1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C7 C15 N1 108.57(10) . . ?
C7 C15 P1 128.27(9) . . ?
N1 C15 P1 122.76(9) . . ?
C21 C16 C17 108.82(10) . . ?
C21 C16 P1 112.15(9) . . ?
C17 C16 P1 112.01(9) . . ?
C21 C16 H16 107.9 . . ?
C17 C16 H16 107.9 . . ?
P1 C16 H16 107.9 . . ?
C18 C17 C16 109.95(11) . . ?
C18 C17 H17A 109.7 . . ?
C16 C17 H17A 109.7 . . ?
C18 C17 H17B 109.7 . . ?
C16 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
C19 C18 C17 111.66(11) . . ?
C19 C18 H18A 109.3 . . ?
C17 C18 H18A 109.3 . . ?
C19 C18 H18B 109.3 . . ?
C17 C18 H18B 109.3 . . ?
H18A C18 H18B 107.9 . . ?
C18 C19 C20 110.78(11) . . ?
C18 C19 H19A 109.5 . . ?
C20 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
C20 C19 H19B 109.5 . . ?
H19A C19 H19B 108.1 . . ?
C21 C20 C19 112.16(12) . . ?
C21 C20 H20A 109.2 . . ?
C19 C20 H20A 109.2 . . ?
C21 C20 H20B 109.2 . . ?
C19 C20 H20B 109.2 . . ?
H20A C20 H20B 107.9 . . ?
C20 C21 C16 110.93(11) . . ?
C20 C21 H21A 109.5 . . ?
C16 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C16 C21 H21B 109.5 . . ?
H21A C21 H21B 108.0 . . ?
C27 C22 C23 110.11(10) . . ?
C27 C22 P1 114.28(9) . . ?
C23 C22 P1 110.20(9) . . ?
C27 C22 H22 107.3 . . ?
C23 C22 H22 107.3 . . ?
P1 C22 H22 107.3 . . ?
C24 C23 C22 110.77(11) . . ?
C24 C23 H23A 109.5 . . ?
C22 C23 H23A 109.5 . . ?
C24 C23 H23B 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 108.1 . . ?
C25 C24 C23 111.23(11) . . ?
C25 C24 H24A 109.4 . . ?
C23 C24 H24A 109.4 . . ?
C25 C24 H24B 109.4 . . ?
C23 C24 H24B 109.4 . . ?
H24A C24 H24B 108.0 . . ?
C26 C25 C24 111.12(11) . . ?
C26 C25 H25A 109.4 . . ?
C24 C25 H25A 109.4 . . ?
C26 C25 H25B 109.4 . . ?
C24 C25 H25B 109.4 . . ?
H25A C25 H25B 108.0 . . ?
C25 C26 C27 111.78(11) . . ?
C25 C26 H26A 109.3 . . ?
C27 C26 H26A 109.3 . . ?
C25 C26 H26B 109.3 . . ?
C27 C26 H26B 109.3 . . ?
H26A C26 H26B 107.9 . . ?
C26 C27 C22 110.22(10) . . ?
C26 C27 H27A 109.6 . . ?
C22 C27 H27A 109.6 . . ?
C26 C27 H27B 109.6 . . ?
C22 C27 H27B 109.6 . . ?
H27A C27 H27B 108.1 . . ?
H2A O2 H2A' 112.3 . . ?

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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C15 N1 C1 C2 -178.39(12) . . . . ?
C14 N1 C1 C2 3.0(2) . . . . ?
C15 N1 C1 C6 0.91(13) . . . . ?
C14 N1 C1 C6 -177.74(11) . . . . ?
N1 C1 C2 C3 -179.89(12) . . . . ?
C6 C1 C2 C3 0.88(18) . . . . ?
C1 C2 C3 C4 0.43(19) . . . . ?
C2 C3 C4 C5 -0.6(2) . . . . ?
C3 C4 C5 C6 -0.45(18) . . . . ?
C4 C5 C6 C1 1.72(17) . . . . ?
C4 C5 C6 C7 -177.26(12) . . . . ?
N1 C1 C6 C5 178.65(10) . . . . ?
C2 C1 C6 C5 -1.98(18) . . . . ?
N1 C1 C6 C7 -2.14(13) . . . . ?
C2 C1 C6 C7 177.23(11) . . . . ?
C5 C6 C7 C15 -178.38(13) . . . . ?
C1 C6 C7 C15 2.56(13) . . . . ?
C5 C6 C7 C8 3.7(2) . . . . ?
C1 C6 C7 C8 -175.38(11) . . . . ?
C15 C7 C8 C13 122.00(14) . . . . ?
C6 C7 C8 C13 -60.56(16) . . . . ?
C15 C7 C8 C9 -60.48(18) . . . . ?
C6 C7 C8 C9 116.96(13) . . . . ?
C13 C8 C9 C10 -2.56(17) . . . . ?
C7 C8 C9 C10 179.89(11) . . . . ?
C8 C9 C10 C11 1.07(19) . . . . ?
C9 C10 C11 C12 0.7(2) . . . . ?
C10 C11 C12 C13 -1.0(2) . . . . ?
C11 C12 C13 C8 -0.6(2) . . . . ?
C9 C8 C13 C12 2.31(18) . . . . ?
C7 C8 C13 C12 179.92(11) . . . . ?
C6 C7 C15 N1 -2.03(13) . . . . ?
C8 C7 C15 N1 175.73(11) . . . . ?
C6 C7 C15 P1 170.84(9) . . . . ?
C8 C7 C15 P1 -11.41(19) . . . . ?
C1 N1 C15 C7 0.72(13) . . . . ?
C14 N1 C15 C7 179.27(12) . . . . ?
C1 N1 C15 P1 -172.62(9) . . . . ?
C14 N1 C15 P1 5.93(18) . . . . ?
O1 P1 C15 C7 -158.48(11) . . . . ?
C22 P1 C15 C7 -36.28(12) . . . . ?
C16 P1 C15 C7 76.86(12) . . . . ?
O1 P1 C15 N1 13.47(12) . . . . ?
C22 P1 C15 N1 135.67(10) . . . . ?
C16 P1 C15 N1 -111.19(10) . . . . ?
O1 P1 C16 C21 -86.54(10) . . . . ?
C15 P1 C16 C21 38.00(10) . . . . ?
C22 P1 C16 C21 147.05(9) . . . . ?
O1 P1 C16 C17 36.15(11) . . . . ?
C15 P1 C16 C17 160.70(9) . . . . ?
C22 P1 C16 C17 -90.25(10) . . . . ?
C21 C16 C17 C18 -59.76(14) . . . . ?
P1 C16 C17 C18 175.68(9) . . . . ?
C16 C17 C18 C19 58.58(15) . . . . ?
C17 C18 C19 C20 -54.45(17) . . . . ?
C18 C19 C20 C21 52.97(18) . . . . ?
C19 C20 C21 C16 -55.87(17) . . . . ?
C17 C16 C21 C20 58.56(15) . . . . ?
P1 C16 C21 C20 -176.95(10) . . . . ?
O1 P1 C22 C27 -67.90(10) . . . . ?
C15 P1 C22 C27 170.23(9) . . . . ?
C16 P1 C22 C27 58.34(10) . . . . ?
O1 P1 C22 C23 56.71(10) . . . . ?
C15 P1 C22 C23 -65.17(10) . . . . ?
C16 P1 C22 C23 -177.06(8) . . . . ?
C27 C22 C23 C24 -57.46(14) . . . . ?
P1 C22 C23 C24 175.58(9) . . . . ?
C22 C23 C24 C25 56.39(16) . . . . ?
C23 C24 C25 C26 -55.07(17) . . . . ?
C24 C25 C26 C27 55.46(16) . . . . ?
C25 C26 C27 C22 -56.66(15) . . . . ?
C23 C22 C27 C26 57.22(14) . . . . ?
P1 C22 C27 C26 -178.13(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2A O1 0.90 2.05 2.8356(15) 144.6 3_445
O2 H2A' O1 0.91 1.94 2.8356(15) 170.2 4_646

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.614
_refine_diff_density_rms         0.044
####################################################################### 
# 
# 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_shelx_sq
_database_code_depnum_ccdc_archive 'CCDC 1563421'
_audit_update_record             
;
2017-07-20 deposited with the CCDC.
2017-09-22 downloaded from the CCDC.
;
_audit_creation_date             2017-03-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2014/8
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C28 H24 N O2 P'
_chemical_formula_sum            'C28 H24 N O2 P'
_chemical_formula_weight         437.45
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
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'
'-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                   24.609(6)
_cell_length_b                   9.508(2)
_cell_length_c                   21.415(5)
_cell_angle_alpha                90
_cell_angle_beta                 115.972(4)
_cell_angle_gamma                90
_cell_volume                     4504.5(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6054
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.3
_shelx_estimated_absorpt_T_max   0.982
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.479
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    "'not measured'"
_exptl_crystal_description       prism
_exptl_crystal_F_000             1840
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0964
_diffrn_reflns_av_unetI/netI     0.0656
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            22409
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.543
_diffrn_reflns_theta_min         3.284
_diffrn_ambient_temperature      213.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Rigaku Xtalab P200'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4013
_reflns_number_total             5094
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.1 b42 (Rigaku, 2015)'
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalClear
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.479
_refine_diff_density_min         -0.459
_refine_diff_density_rms         0.086
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         5094
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0569
_refine_ls_R_factor_gt           0.0471
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0886P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1320
_refine_ls_wR_factor_ref         0.1488
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C9(H9), C10(H10), C11(H11), C12(H12), C13(H13),
 C16(H16), C17(H17), C18(H18), C19(H19), C20(H20), C22(H22), C23(H23), C24(H24),
  C25(H25), C26(H26)
2.b Idealised Me refined as rotating group:
 C27(H27A,H27B,H27C), C28(H28A,H28B,H28C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.09017(2) 0.15111(4) 0.17445(2) 0.02001(14) Uani 1 1 d . . . . .
O1 O 0.40957(6) 0.16806(15) 0.47977(7) 0.0353(3) Uani 1 1 d . . . . .
O2 O 0.04857(6) 0.03540(13) 0.17195(6) 0.0294(3) Uani 1 1 d . . . . .
N1 N 0.16572(7) 0.13649(15) 0.31385(7) 0.0248(3) Uani 1 1 d . . . . .
C1 C 0.22500(8) 0.14202(17) 0.36191(9) 0.0233(4) Uani 1 1 d . . . . .
C2 C 0.25032(9) 0.13960(19) 0.43473(9) 0.0285(4) Uani 1 1 d . . . . .
H2 H 0.2259 0.1323 0.4582 0.034 Uiso 1 1 calc R . . . .
C3 C 0.31152(9) 0.14825(19) 0.47017(9) 0.0299(4) Uani 1 1 d . . . . .
H3 H 0.3293 0.1474 0.5190 0.036 Uiso 1 1 calc R . . . .
C4 C 0.34941(9) 0.15855(18) 0.43626(9) 0.0267(4) Uani 1 1 d . . . . .
C5 C 0.32496(8) 0.15712(16) 0.36414(9) 0.0225(4) Uani 1 1 d . . . . .
H5 H 0.3499 0.1607 0.3412 0.027 Uiso 1 1 calc R . . . .
C6 C 0.26161(8) 0.15012(15) 0.32663(8) 0.0194(3) Uani 1 1 d . . . . .
C7 C 0.22188(8) 0.14752(15) 0.25408(8) 0.0182(3) Uani 1 1 d . . . . .
C8 C 0.24284(8) 0.14756(16) 0.19875(8) 0.0182(3) Uani 1 1 d . . . . .
C9 C 0.27509(8) 0.26134(18) 0.19113(9) 0.0246(4) Uani 1 1 d . . . . .
H9 H 0.2838 0.3386 0.2214 0.030 Uiso 1 1 calc R . . . .
C10 C 0.29444(9) 0.2614(2) 0.13906(10) 0.0336(4) Uani 1 1 d . . . . .
H10 H 0.3158 0.3391 0.1340 0.040 Uiso 1 1 calc R . . . .
C11 C 0.28244(10) 0.1478(2) 0.09467(10) 0.0342(5) Uani 1 1 d . . . . .
H11 H 0.2952 0.1485 0.0592 0.041 Uiso 1 1 calc R . . . .
C12 C 0.25156(9) 0.0332(2) 0.10282(9) 0.0306(4) Uani 1 1 d . . . . .
H12 H 0.2436 -0.0446 0.0730 0.037 Uiso 1 1 calc R . . . .
C13 C 0.23219(8) 0.03254(17) 0.15489(8) 0.0225(4) Uani 1 1 d . . . . .
H13 H 0.2117 -0.0464 0.1604 0.027 Uiso 1 1 calc R . . . .
C14 C 0.16338(8) 0.14025(17) 0.24788(8) 0.0221(4) Uani 1 1 d . . . . .
C15 C 0.06210(8) 0.32221(17) 0.18198(8) 0.0210(3) Uani 1 1 d . . . . .
C16 C 0.09878(8) 0.42965(19) 0.22329(9) 0.0272(4) Uani 1 1 d . . . . .
H16 H 0.1402 0.4138 0.2507 0.033 Uiso 1 1 calc R . . . .
C17 C 0.07370(10) 0.5606(2) 0.22380(10) 0.0325(4) Uani 1 1 d . . . . .
H17 H 0.0983 0.6331 0.2518 0.039 Uiso 1 1 calc R . . . .
C18 C 0.01285(10) 0.5845(2) 0.18333(10) 0.0345(5) Uani 1 1 d . . . . .
H18 H -0.0038 0.6732 0.1839 0.041 Uiso 1 1 calc R . . . .
C19 C -0.02363(9) 0.4783(2) 0.14192(10) 0.0327(4) Uani 1 1 d . . . . .
H19 H -0.0650 0.4951 0.1141 0.039 Uiso 1 1 calc R . . . .
C20 C 0.00063(8) 0.34762(19) 0.14136(9) 0.0257(4) Uani 1 1 d . . . . .
H20 H -0.0243 0.2754 0.1135 0.031 Uiso 1 1 calc R . . . .
C21 C 0.09922(8) 0.16097(16) 0.09568(8) 0.0192(3) Uani 1 1 d . . . . .
C22 C 0.12334(8) 0.27895(17) 0.07814(8) 0.0212(3) Uani 1 1 d . . . . .
H22 H 0.1382 0.3542 0.1096 0.025 Uiso 1 1 calc R . . . .
C23 C 0.12547(8) 0.28568(19) 0.01517(9) 0.0268(4) Uani 1 1 d . . . . .
H23 H 0.1427 0.3644 0.0042 0.032 Uiso 1 1 calc R . . . .
C24 C 0.10216(9) 0.1764(2) -0.03227(10) 0.0315(4) Uani 1 1 d . . . . .
H24 H 0.1030 0.1819 -0.0757 0.038 Uiso 1 1 calc R . . . .
C25 C 0.07786(9) 0.0601(2) -0.01559(10) 0.0335(4) Uani 1 1 d . . . . .
H25 H 0.0623 -0.0140 -0.0476 0.040 Uiso 1 1 calc R . . . .
C26 C 0.07631(8) 0.05174(18) 0.04802(9) 0.0267(4) Uani 1 1 d . . . . .
H26 H 0.0597 -0.0280 0.0591 0.032 Uiso 1 1 calc R . . . .
C27 C 0.11523(10) 0.1376(3) 0.33224(11) 0.0430(6) Uani 1 1 d . . . . .
H27A H 0.1215 0.0658 0.3669 0.065 Uiso 1 1 calc GR . . . .
H27B H 0.0780 0.1185 0.2912 0.065 Uiso 1 1 calc GR . . . .
H27C H 0.1127 0.2291 0.3508 0.065 Uiso 1 1 calc GR . . . .
C28 C 0.45070(9) 0.1555(2) 0.44997(10) 0.0342(5) Uani 1 1 d . . . . .
H28A H 0.4456 0.0645 0.4276 0.051 Uiso 1 1 calc GR . . . .
H28B H 0.4917 0.1641 0.4861 0.051 Uiso 1 1 calc GR . . . .
H28C H 0.4429 0.2293 0.4158 0.051 Uiso 1 1 calc GR . . . .


_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 O2 1.4878(12) . ?
P1 C14 1.8021(19) . ?
P1 C15 1.8021(17) . ?
P1 C21 1.7979(16) . ?
O1 C4 1.364(2) . ?
O1 C28 1.418(2) . ?
N1 C1 1.369(2) . ?
N1 C14 1.389(2) . ?
N1 C27 1.458(2) . ?
C1 C2 1.403(2) . ?
C1 C6 1.409(2) . ?
C2 H2 0.9400 . ?
C2 C3 1.360(3) . ?
C3 H3 0.9400 . ?
C3 C4 1.414(3) . ?
C4 C5 1.391(2) . ?
C5 H5 0.9400 . ?
C5 C6 1.408(2) . ?
C6 C7 1.428(2) . ?
C7 C8 1.485(2) . ?
C7 C14 1.388(2) . ?
C8 C9 1.393(2) . ?
C8 C13 1.390(2) . ?
C9 H9 0.9400 . ?
C9 C10 1.391(2) . ?
C10 H10 0.9400 . ?
C10 C11 1.382(3) . ?
C11 H11 0.9400 . ?
C11 C12 1.383(3) . ?
C12 H12 0.9400 . ?
C12 C13 1.392(2) . ?
C13 H13 0.9400 . ?
C15 C16 1.393(2) . ?
C15 C20 1.397(2) . ?
C16 H16 0.9400 . ?
C16 C17 1.391(3) . ?
C17 H17 0.9400 . ?
C17 C18 1.382(3) . ?
C18 H18 0.9400 . ?
C18 C19 1.384(3) . ?
C19 H19 0.9400 . ?
C19 C20 1.381(3) . ?
C20 H20 0.9400 . ?
C21 C22 1.395(2) . ?
C21 C26 1.391(2) . ?
C22 H22 0.9400 . ?
C22 C23 1.374(2) . ?
C23 H23 0.9400 . ?
C23 C24 1.389(3) . ?
C24 H24 0.9400 . ?
C24 C25 1.377(3) . ?
C25 H25 0.9400 . ?
C25 C26 1.382(2) . ?
C26 H26 0.9400 . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C27 H27C 0.9700 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 H28C 0.9700 . ?

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
O2 P1 C14 113.47(7) . . ?
O2 P1 C15 112.70(8) . . ?
O2 P1 C21 111.77(7) . . ?
C14 P1 C15 104.45(8) . . ?
C21 P1 C14 109.54(8) . . ?
C21 P1 C15 104.29(7) . . ?
C4 O1 C28 117.52(14) . . ?
C1 N1 C14 108.62(14) . . ?
C1 N1 C27 123.37(14) . . ?
C14 N1 C27 127.86(16) . . ?
N1 C1 C2 130.00(16) . . ?
N1 C1 C6 108.67(14) . . ?
C2 C1 C6 121.33(17) . . ?
C1 C2 H2 121.2 . . ?
C3 C2 C1 117.60(16) . . ?
C3 C2 H2 121.2 . . ?
C2 C3 H3 118.8 . . ?
C2 C3 C4 122.39(17) . . ?
C4 C3 H3 118.8 . . ?
O1 C4 C3 114.61(16) . . ?
O1 C4 C5 124.86(17) . . ?
C5 C4 C3 120.52(18) . . ?
C4 C5 H5 121.1 . . ?
C4 C5 C6 117.79(16) . . ?
C6 C5 H5 121.1 . . ?
C1 C6 C7 106.77(16) . . ?
C5 C6 C1 120.33(15) . . ?
C5 C6 C7 132.89(15) . . ?
C6 C7 C8 123.82(15) . . ?
C14 C7 C6 106.98(14) . . ?
C14 C7 C8 129.16(15) . . ?
C9 C8 C7 120.56(14) . . ?
C13 C8 C7 120.70(14) . . ?
C13 C8 C9 118.72(14) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.44(15) . . ?
C10 C9 H9 119.8 . . ?
C9 C10 H10 119.8 . . ?
C11 C10 C9 120.40(17) . . ?
C11 C10 H10 119.8 . . ?
C10 C11 H11 120.2 . . ?
C10 C11 C12 119.51(16) . . ?
C12 C11 H11 120.2 . . ?
C11 C12 H12 119.8 . . ?
C11 C12 C13 120.33(16) . . ?
C13 C12 H12 119.8 . . ?
C8 C13 C12 120.57(15) . . ?
C8 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
N1 C14 P1 117.98(13) . . ?
C7 C14 P1 132.78(12) . . ?
C7 C14 N1 108.95(15) . . ?
C16 C15 P1 123.46(13) . . ?
C16 C15 C20 119.50(16) . . ?
C20 C15 P1 116.97(13) . . ?
C15 C16 H16 120.2 . . ?
C17 C16 C15 119.64(18) . . ?
C17 C16 H16 120.2 . . ?
C16 C17 H17 119.8 . . ?
C18 C17 C16 120.35(18) . . ?
C18 C17 H17 119.8 . . ?
C17 C18 H18 119.9 . . ?
C17 C18 C19 120.15(18) . . ?
C19 C18 H18 119.9 . . ?
C18 C19 H19 120.0 . . ?
C20 C19 C18 120.05(18) . . ?
C20 C19 H19 120.0 . . ?
C15 C20 H20 119.8 . . ?
C19 C20 C15 120.31(17) . . ?
C19 C20 H20 119.8 . . ?
C22 C21 P1 122.44(12) . . ?
C26 C21 P1 118.21(12) . . ?
C26 C21 C22 119.10(15) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 C21 120.35(15) . . ?
C23 C22 H22 119.8 . . ?
C22 C23 H23 119.9 . . ?
C22 C23 C24 120.13(16) . . ?
C24 C23 H23 119.9 . . ?
C23 C24 H24 120.1 . . ?
C25 C24 C23 119.88(16) . . ?
C25 C24 H24 120.1 . . ?
C24 C25 H25 119.8 . . ?
C24 C25 C26 120.30(17) . . ?
C26 C25 H25 119.8 . . ?
C21 C26 H26 119.9 . . ?
C25 C26 C21 120.22(16) . . ?
C25 C26 H26 119.9 . . ?
N1 C27 H27A 109.5 . . ?
N1 C27 H27B 109.5 . . ?
N1 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O1 C28 H28A 109.5 . . ?
O1 C28 H28B 109.5 . . ?
O1 C28 H28C 109.5 . . ?
H28A C28 H28B 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C15 C16 C17 177.31(13) . . . . ?
P1 C15 C20 C19 -177.02(13) . . . . ?
P1 C21 C22 C23 -175.42(13) . . . . ?
P1 C21 C26 C25 174.79(15) . . . . ?
O1 C4 C5 C6 -178.52(15) . . . . ?
O2 P1 C14 N1 -56.42(14) . . . . ?
O2 P1 C14 C7 130.61(16) . . . . ?
O2 P1 C15 C16 140.81(13) . . . . ?
O2 P1 C15 C20 -42.10(15) . . . . ?
O2 P1 C21 C22 163.90(14) . . . . ?
O2 P1 C21 C26 -10.30(16) . . . . ?
N1 C1 C2 C3 -179.26(17) . . . . ?
N1 C1 C6 C5 179.96(14) . . . . ?
N1 C1 C6 C7 -0.72(18) . . . . ?
C1 N1 C14 P1 -174.24(12) . . . . ?
C1 N1 C14 C7 0.31(18) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
C1 C6 C7 C8 -177.11(14) . . . . ?
C1 C6 C7 C14 0.89(17) . . . . ?
C2 C1 C6 C5 -0.5(2) . . . . ?
C2 C1 C6 C7 178.82(15) . . . . ?
C2 C3 C4 O1 179.22(16) . . . . ?
C2 C3 C4 C5 -1.4(3) . . . . ?
C3 C4 C5 C6 2.2(2) . . . . ?
C4 C5 C6 C1 -1.3(2) . . . . ?
C4 C5 C6 C7 179.63(16) . . . . ?
C5 C6 C7 C8 2.1(3) . . . . ?
C5 C6 C7 C14 -179.91(17) . . . . ?
C6 C1 C2 C3 1.3(2) . . . . ?
C6 C7 C8 C9 -63.2(2) . . . . ?
C6 C7 C8 C13 114.95(18) . . . . ?
C6 C7 C14 P1 172.70(13) . . . . ?
C6 C7 C14 N1 -0.75(17) . . . . ?
C7 C8 C9 C10 -179.72(16) . . . . ?
C7 C8 C13 C12 179.61(16) . . . . ?
C8 C7 C14 P1 -9.4(3) . . . . ?
C8 C7 C14 N1 177.11(14) . . . . ?
C8 C9 C10 C11 -0.7(3) . . . . ?
C9 C8 C13 C12 -2.2(3) . . . . ?
C9 C10 C11 C12 -0.7(3) . . . . ?
C10 C11 C12 C13 0.6(3) . . . . ?
C11 C12 C13 C8 0.9(3) . . . . ?
C13 C8 C9 C10 2.1(3) . . . . ?
C14 P1 C15 C16 17.19(15) . . . . ?
C14 P1 C15 C20 -165.72(12) . . . . ?
C14 P1 C21 C22 -69.46(16) . . . . ?
C14 P1 C21 C26 116.34(14) . . . . ?
C14 N1 C1 C2 -179.22(17) . . . . ?
C14 N1 C1 C6 0.27(18) . . . . ?
C14 C7 C8 C9 119.3(2) . . . . ?
C14 C7 C8 C13 -62.6(2) . . . . ?
C15 P1 C14 N1 66.70(14) . . . . ?
C15 P1 C14 C7 -106.28(17) . . . . ?
C15 P1 C21 C22 41.87(16) . . . . ?
C15 P1 C21 C26 -132.34(14) . . . . ?
C15 C16 C17 C18 -0.4(3) . . . . ?
C16 C15 C20 C19 0.2(2) . . . . ?
C16 C17 C18 C19 0.0(3) . . . . ?
C17 C18 C19 C20 0.5(3) . . . . ?
C18 C19 C20 C15 -0.6(3) . . . . ?
C20 C15 C16 C17 0.3(2) . . . . ?
C21 P1 C14 N1 177.92(12) . . . . ?
C21 P1 C14 C7 4.94(19) . . . . ?
C21 P1 C15 C16 -97.77(15) . . . . ?
C21 P1 C15 C20 79.32(14) . . . . ?
C21 C22 C23 C24 1.7(3) . . . . ?
C22 C21 C26 C25 0.4(3) . . . . ?
C22 C23 C24 C25 -1.2(3) . . . . ?
C23 C24 C25 C26 0.3(3) . . . . ?
C24 C25 C26 C21 0.1(3) . . . . ?
C26 C21 C22 C23 -1.3(3) . . . . ?
C27 N1 C1 C2 5.0(3) . . . . ?
C27 N1 C1 C6 -175.50(16) . . . . ?
C27 N1 C14 P1 1.3(2) . . . . ?
C27 N1 C14 C7 175.83(18) . . . . ?
C28 O1 C4 C3 169.91(16) . . . . ?
C28 O1 C4 C5 -9.4(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
