# Electronic Supplementary Material (ESI) for MedChemComm.
# This journal is © The Royal Society of Chemistry 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_aaaaa
_database_code_depnum_ccdc_archive 'CCDC 1531267'
_audit_update_record             
;
2017-02-06 deposited with the CCDC.
2017-03-30 downloaded from the CCDC.
;
_audit_creation_date             2016-04-13
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C22 H24 N O7 P, C2 H3 N'
_chemical_formula_sum            'C24 H27 N2 O7 P'
_chemical_formula_weight         486.45
_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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   12.598(13)
_cell_length_b                   15.985(17)
_cell_length_c                   12.834(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.364(18)
_cell_angle_gamma                90.00
_cell_volume                     2580(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1340
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.93
_cell_measurement_theta_min      2.54
_exptl_absorpt_coefficient_mu    0.150
_exptl_absorpt_correction_T_max  0.9851
_exptl_absorpt_correction_T_min  0.9549
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.252
_exptl_crystal_density_meas      0
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             1024
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.2060
_diffrn_reflns_av_unetI/netI     0.1728
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            23246
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         1.62
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         0
_reflns_number_gt                2034
_reflns_number_total             5264
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.410
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.934
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         5264
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2159
_refine_ls_R_factor_gt           0.0724
_refine_ls_restrained_S_all      0.934
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0809P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1440
_refine_ls_wR_factor_ref         0.1983
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.35930(10) 0.08553(7) 0.16334(8) 0.0444(4) Uani 1 1 d . . .
O1 O 0.0713(3) 0.5422(2) 0.2179(3) 0.0735(10) Uani 1 1 d . . .
O2 O 0.0858(3) 0.5861(2) 0.0463(3) 0.0735(10) Uani 1 1 d . . .
O3 O 0.4180(3) 0.23969(19) -0.0761(2) 0.0570(9) Uani 1 1 d . . .
O4 O 0.5055(3) 0.1939(2) 0.2302(2) 0.0720(10) Uani 1 1 d . . .
O5 O 0.2927(2) 0.09455(18) 0.2540(2) 0.0523(8) Uani 1 1 d . . .
O6 O 0.4457(3) 0.01372(18) 0.1714(2) 0.0613(9) Uani 1 1 d . . .
O7 O 0.2872(2) 0.0669(2) 0.0609(2) 0.0603(9) Uani 1 1 d . . .
N1 N 0.3098(3) 0.3482(2) -0.0364(2) 0.0447(9) Uani 1 1 d . . .
H1 H 0.3114 0.3650 -0.1000 0.054 Uiso 1 1 calc R . .
N2 N 0.0995(5) 0.2147(4) -0.0721(5) 0.119(2) Uani 1 1 d . . .
C1 C 0.0483(5) 0.6087(3) 0.1453(4) 0.0785(17) Uani 1 1 d . . .
H1A H -0.0278 0.6187 0.1386 0.094 Uiso 1 1 calc R . .
H1B H 0.0829 0.6597 0.1702 0.094 Uiso 1 1 calc R . .
C2 C 0.1356(4) 0.4863(3) 0.1666(4) 0.0553(13) Uani 1 1 d . . .
C3 C 0.1837(4) 0.4156(3) 0.2032(3) 0.0529(12) Uani 1 1 d . . .
H3 H 0.1768 0.3981 0.2716 0.063 Uiso 1 1 calc R . .
C4 C 0.2448(3) 0.3689(3) 0.1345(3) 0.0423(11) Uani 1 1 d . . .
C5 C 0.3056(3) 0.2969(3) 0.1659(3) 0.0463(11) Uani 1 1 d . . .
H5 H 0.3039 0.2791 0.2348 0.056 Uiso 1 1 calc R . .
C6 C 0.3662(3) 0.2525(3) 0.0999(3) 0.0401(10) Uani 1 1 d . . .
C7 C 0.3665(4) 0.2784(3) -0.0100(3) 0.0415(11) Uani 1 1 d . . .
C8 C 0.2495(3) 0.3953(3) 0.0295(3) 0.0419(11) Uani 1 1 d . . .
C9 C 0.1988(4) 0.4690(3) -0.0065(4) 0.0523(12) Uani 1 1 d . . .
H9 H 0.2036 0.4872 -0.0750 0.063 Uiso 1 1 calc R . .
C10 C 0.1429(4) 0.5126(3) 0.0621(4) 0.0546(12) Uani 1 1 d . . .
C11 C 0.6047(3) 0.2364(3) 0.2234(3) 0.0397(10) Uani 1 1 d . . .
C12 C 0.6465(4) 0.2620(3) 0.1311(3) 0.0504(12) Uani 1 1 d . . .
H12 H 0.6094 0.2516 0.0676 0.060 Uiso 1 1 calc R . .
C13 C 0.7442(4) 0.3032(3) 0.1333(4) 0.0597(13) Uani 1 1 d . . .
H13 H 0.7715 0.3188 0.0704 0.072 Uiso 1 1 calc R . .
C14 C 0.8022(4) 0.3217(3) 0.2251(4) 0.0626(14) Uani 1 1 d . . .
C15 C 0.9055(4) 0.3712(4) 0.2298(5) 0.098(2) Uani 1 1 d . . .
H15A H 0.8910 0.4288 0.2445 0.146 Uiso 1 1 calc R . .
H15B H 0.9377 0.3671 0.1640 0.146 Uiso 1 1 calc R . .
H15C H 0.9532 0.3489 0.2839 0.146 Uiso 1 1 calc R . .
C16 C 0.7604(4) 0.2937(3) 0.3164(4) 0.0676(15) Uani 1 1 d . . .
H16 H 0.7988 0.3032 0.3794 0.081 Uiso 1 1 calc R . .
C17 C 0.6638(4) 0.2522(3) 0.3178(3) 0.0568(13) Uani 1 1 d . . .
H17 H 0.6383 0.2349 0.3808 0.068 Uiso 1 1 calc R . .
C18 C 0.4361(3) 0.1780(3) 0.1362(3) 0.0393(11) Uani 1 1 d . . .
H18 H 0.4819 0.1641 0.0795 0.047 Uiso 1 1 calc R . .
C19 C 0.4576(5) -0.0469(3) 0.2549(4) 0.0878(19) Uani 1 1 d . . .
H19A H 0.4969 -0.0947 0.2310 0.105 Uiso 1 1 calc R . .
H19B H 0.3878 -0.0663 0.2720 0.105 Uiso 1 1 calc R . .
C20 C 0.5139(6) -0.0122(4) 0.3505(5) 0.111(2) Uani 1 1 d . . .
H20A H 0.5837 0.0061 0.3343 0.166 Uiso 1 1 calc R . .
H20B H 0.5199 -0.0546 0.4034 0.166 Uiso 1 1 calc R . .
H20C H 0.4746 0.0344 0.3754 0.166 Uiso 1 1 calc R . .
C21 C 0.3278(6) 0.0357(4) -0.0352(4) 0.103(2) Uani 1 1 d . . .
H21A H 0.4042 0.0285 -0.0259 0.124 Uiso 1 1 calc R . .
H21B H 0.3134 0.0762 -0.0905 0.124 Uiso 1 1 calc R . .
C22 C 0.2783(7) -0.0443(4) -0.0653(5) 0.143(3) Uani 1 1 d . . .
H22A H 0.2961 -0.0586 -0.1348 0.215 Uiso 1 1 calc R . .
H22B H 0.2025 -0.0397 -0.0630 0.215 Uiso 1 1 calc R . .
H22C H 0.3039 -0.0871 -0.0177 0.215 Uiso 1 1 calc R . .
C23 C 0.0773(6) 0.1958(5) 0.0084(7) 0.100(2) Uani 1 1 d . . .
C24 C 0.0494(6) 0.1694(6) 0.1115(7) 0.155(3) Uani 1 1 d . . .
H24A H 0.0197 0.1142 0.1076 0.232 Uiso 1 1 calc R . .
H24B H -0.0018 0.2075 0.1373 0.232 Uiso 1 1 calc R . .
H24C H 0.1120 0.1692 0.1579 0.232 Uiso 1 1 calc R . .


_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 O5 1.481(3) . ?
P1 O6 1.581(3) . ?
P1 O7 1.582(3) . ?
P1 C18 1.812(4) . ?
O1 C1 1.433(6) . ?
O1 C2 1.396(5) . ?
O2 C1 1.427(6) . ?
O2 C10 1.386(5) . ?
O3 C7 1.260(5) . ?
O4 C11 1.429(5) . ?
O4 C18 1.470(5) . ?
O6 C19 1.445(6) . ?
O7 C21 1.451(6) . ?
N1 H1 0.8600 . ?
N1 C7 1.358(5) . ?
N1 C8 1.390(5) . ?
N2 C23 1.128(8) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.353(6) . ?
C2 C10 1.414(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.417(6) . ?
C4 C5 1.427(6) . ?
C4 C8 1.417(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.371(5) . ?
C6 C7 1.470(5) . ?
C6 C18 1.537(6) . ?
C8 C9 1.406(6) . ?
C9 H9 0.9300 . ?
C9 C10 1.353(6) . ?
C11 C12 1.387(5) . ?
C11 C17 1.408(6) . ?
C12 H12 0.9300 . ?
C12 C13 1.395(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.381(7) . ?
C14 C15 1.522(7) . ?
C14 C16 1.387(7) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16 0.9300 . ?
C16 C17 1.387(6) . ?
C17 H17 0.9300 . ?
C18 H18 0.9800 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.489(8) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.465(9) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.452(11) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

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
O5 P1 O6 116.01(17) . . ?
O5 P1 O7 110.32(19) . . ?
O5 P1 C18 113.91(18) . . ?
O6 P1 O7 106.10(18) . . ?
O6 P1 C18 103.4(2) . . ?
O7 P1 C18 106.34(18) . . ?
C2 O1 C1 105.6(4) . . ?
C10 O2 C1 106.3(4) . . ?
C11 O4 C18 120.8(3) . . ?
C19 O6 P1 125.2(3) . . ?
C21 O7 P1 123.9(3) . . ?
C7 N1 H1 116.9 . . ?
C7 N1 C8 126.2(3) . . ?
C8 N1 H1 116.9 . . ?
O1 C1 H1A 109.9 . . ?
O1 C1 H1B 109.9 . . ?
O2 C1 O1 109.0(4) . . ?
O2 C1 H1A 109.9 . . ?
O2 C1 H1B 109.9 . . ?
H1A C1 H1B 108.3 . . ?
O1 C2 C10 109.2(4) . . ?
C3 C2 O1 129.2(4) . . ?
C3 C2 C10 121.6(4) . . ?
C2 C3 H3 120.9 . . ?
C2 C3 C4 118.2(4) . . ?
C4 C3 H3 120.9 . . ?
C3 C4 C5 123.4(4) . . ?
C8 C4 C3 119.3(4) . . ?
C8 C4 C5 117.2(4) . . ?
C4 C5 H5 118.3 . . ?
C6 C5 C4 123.5(4) . . ?
C6 C5 H5 118.3 . . ?
C5 C6 C7 118.7(4) . . ?
C5 C6 C18 122.9(4) . . ?
C7 C6 C18 118.4(4) . . ?
O3 C7 N1 121.3(4) . . ?
O3 C7 C6 122.5(4) . . ?
N1 C7 C6 116.1(4) . . ?
N1 C8 C4 118.2(4) . . ?
N1 C8 C9 120.5(4) . . ?
C9 C8 C4 121.3(4) . . ?
C8 C9 H9 121.3 . . ?
C10 C9 C8 117.5(4) . . ?
C10 C9 H9 121.3 . . ?
O2 C10 C2 109.2(4) . . ?
C9 C10 O2 128.8(4) . . ?
C9 C10 C2 122.0(5) . . ?
C12 C11 O4 124.8(4) . . ?
C12 C11 C17 118.3(4) . . ?
C17 C11 O4 117.0(4) . . ?
C11 C12 H12 120.0 . . ?
C11 C12 C13 120.1(4) . . ?
C13 C12 H12 120.0 . . ?
C12 C13 H13 118.6 . . ?
C14 C13 C12 122.7(4) . . ?
C14 C13 H13 118.6 . . ?
C13 C14 C15 123.6(5) . . ?
C13 C14 C16 116.4(5) . . ?
C16 C14 C15 120.0(5) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16 118.6 . . ?
C14 C16 C17 122.8(5) . . ?
C17 C16 H16 118.6 . . ?
C11 C17 H17 120.2 . . ?
C16 C17 C11 119.7(4) . . ?
C16 C17 H17 120.2 . . ?
P1 C18 H18 107.6 . . ?
O4 C18 P1 106.4(3) . . ?
O4 C18 C6 114.7(3) . . ?
O4 C18 H18 107.6 . . ?
C6 C18 P1 112.8(3) . . ?
C6 C18 H18 107.6 . . ?
O6 C19 H19A 109.1 . . ?
O6 C19 H19B 109.1 . . ?
O6 C19 C20 112.6(5) . . ?
H19A C19 H19B 107.8 . . ?
C20 C19 H19A 109.1 . . ?
C20 C19 H19B 109.1 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20B 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O7 C21 H21A 109.4 . . ?
O7 C21 H21B 109.4 . . ?
O7 C21 C22 111.0(6) . . ?
H21A C21 H21B 108.0 . . ?
C22 C21 H21A 109.4 . . ?
C22 C21 H21B 109.4 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N2 C23 C24 178.6(9) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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 O6 C19 C20 -78.9(6) . . . . ?
P1 O7 C21 C22 120.9(5) . . . . ?
O1 C2 C3 C4 179.5(4) . . . . ?
O1 C2 C10 O2 1.3(5) . . . . ?
O1 C2 C10 C9 -178.7(4) . . . . ?
O4 C11 C12 C13 179.9(4) . . . . ?
O4 C11 C17 C16 -179.6(4) . . . . ?
O5 P1 O6 C19 5.7(5) . . . . ?
O5 P1 O7 C21 -165.0(4) . . . . ?
O5 P1 C18 O4 59.9(3) . . . . ?
O5 P1 C18 C6 -66.6(3) . . . . ?
O6 P1 O7 C21 -38.6(4) . . . . ?
O6 P1 C18 O4 -66.8(3) . . . . ?
O6 P1 C18 C6 166.7(3) . . . . ?
O7 P1 O6 C19 -117.2(4) . . . . ?
O7 P1 C18 O4 -178.3(2) . . . . ?
O7 P1 C18 C6 55.1(3) . . . . ?
N1 C8 C9 C10 -178.8(4) . . . . ?
C1 O1 C2 C3 175.9(5) . . . . ?
C1 O1 C2 C10 -6.0(5) . . . . ?
C1 O2 C10 C2 3.9(5) . . . . ?
C1 O2 C10 C9 -176.1(5) . . . . ?
C2 O1 C1 O2 8.5(6) . . . . ?
C2 C3 C4 C5 175.2(4) . . . . ?
C2 C3 C4 C8 -3.0(6) . . . . ?
C3 C2 C10 O2 179.6(4) . . . . ?
C3 C2 C10 C9 -0.4(7) . . . . ?
C3 C4 C5 C6 -178.8(4) . . . . ?
C3 C4 C8 N1 -179.9(4) . . . . ?
C3 C4 C8 C9 3.1(6) . . . . ?
C4 C5 C6 C7 -2.0(6) . . . . ?
C4 C5 C6 C18 176.5(4) . . . . ?
C4 C8 C9 C10 -1.9(6) . . . . ?
C5 C4 C8 N1 1.8(6) . . . . ?
C5 C4 C8 C9 -175.2(4) . . . . ?
C5 C6 C7 O3 -178.2(4) . . . . ?
C5 C6 C7 N1 3.3(6) . . . . ?
C5 C6 C18 P1 72.7(4) . . . . ?
C5 C6 C18 O4 -49.3(5) . . . . ?
C7 N1 C8 C4 -0.4(6) . . . . ?
C7 N1 C8 C9 176.7(4) . . . . ?
C7 C6 C18 P1 -108.8(4) . . . . ?
C7 C6 C18 O4 129.2(4) . . . . ?
C8 N1 C7 O3 179.3(4) . . . . ?
C8 N1 C7 C6 -2.2(6) . . . . ?
C8 C4 C5 C6 -0.6(6) . . . . ?
C8 C9 C10 O2 -179.5(4) . . . . ?
C8 C9 C10 C2 0.5(7) . . . . ?
C10 O2 C1 O1 -7.7(6) . . . . ?
C10 C2 C3 C4 1.7(7) . . . . ?
C11 O4 C18 P1 152.9(3) . . . . ?
C11 O4 C18 C6 -81.7(4) . . . . ?
C11 C12 C13 C14 -1.2(7) . . . . ?
C12 C11 C17 C16 1.1(7) . . . . ?
C12 C13 C14 C15 -176.2(5) . . . . ?
C12 C13 C14 C16 2.8(8) . . . . ?
C13 C14 C16 C17 -2.5(8) . . . . ?
C14 C16 C17 C11 0.6(8) . . . . ?
C15 C14 C16 C17 176.5(5) . . . . ?
C17 C11 C12 C13 -0.8(6) . . . . ?
C18 P1 O6 C19 131.1(4) . . . . ?
C18 P1 O7 C21 71.0(4) . . . . ?
C18 O4 C11 C12 -3.4(6) . . . . ?
C18 O4 C11 C17 177.3(4) . . . . ?
C18 C6 C7 O3 3.2(6) . . . . ?
C18 C6 C7 N1 -175.2(3) . . . . ?

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

data_20160118-zy-yyc-20151229-4
_database_code_depnum_ccdc_archive 'CCDC 1531266'
_audit_update_record             
;
2017-02-06 deposited with the CCDC.
2017-03-30 downloaded from the CCDC.
;
_audit_creation_date             2016-01-23
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C21 H24 N3 O7 P'
_chemical_formula_sum            'C21 H24 N3 O7 P'
_chemical_formula_weight         461.40
_chemical_melting_point          ?
_chemical_oxdiff_formula         C
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, -y, -z'

_cell_length_a                   8.0905(8)
_cell_length_b                   11.3328(17)
_cell_length_c                   11.780(4)
_cell_angle_alpha                91.967(17)
_cell_angle_beta                 90.537(14)
_cell_angle_gamma                99.464(10)
_cell_volume                     1064.6(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1277
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.2010
_cell_measurement_theta_min      3.6330
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             484
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_unetI/netI     0.1201
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            8619
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.35
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 15.9784
_diffrn_measured_fraction_theta_full 0.9970
_diffrn_measured_fraction_theta_max 0.8785
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    3.00   57.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       17.9729  -99.0000  -60.0000 54

#__ type_ start__ end____ width___ exp.time_
  2 omega   30.00   57.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       17.9729  -99.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
  3 omega  -11.00   87.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       17.9729   77.0000 -180.0000 98

#__ type_ start__ end____ width___ exp.time_
  4 omega  -49.00   31.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       17.9729  -57.0000  -60.0000 80

#__ type_ start__ end____ width___ exp.time_
  5 omega  -20.00   87.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       17.9729   19.0000  120.0000 107

#__ type_ start__ end____ width___ exp.time_
  6 omega  -54.00  -15.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       17.9729  -19.0000   60.0000 39
;
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0070994000
_diffrn_orient_matrix_UB_12      -0.0601934000
_diffrn_orient_matrix_UB_13      0.0166050000
_diffrn_orient_matrix_UB_21      0.0084732000
_diffrn_orient_matrix_UB_22      0.0197907000
_diffrn_orient_matrix_UB_23      0.0578737000
_diffrn_orient_matrix_UB_31      -0.0882489000
_diffrn_orient_matrix_UB_32      -0.0038654000
_diffrn_orient_matrix_UB_33      0.0032937000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                2256
_reflns_number_total             4332
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.335
_refine_diff_density_min         -0.391
_refine_diff_density_rms         0.070
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     292
_refine_ls_number_reflns         4332
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1490
_refine_ls_R_factor_gt           0.0741
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0712P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1522
_refine_ls_wR_factor_ref         0.2001
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.81894(13) 0.13782(10) 0.02135(10) 0.0384(3) Uani 1 1 d . . .
O1 O 0.7724(3) 0.0226(2) -0.0386(2) 0.0456(8) Uani 1 1 d . . .
O2 O 0.6748(3) 0.2127(3) 0.0463(3) 0.0497(8) Uani 1 1 d . . .
O3 O 0.9515(3) 0.2291(2) -0.0408(3) 0.0478(8) Uani 1 1 d . . .
O4 O 0.1240(3) -0.2226(3) 0.3734(3) 0.0615(10) Uani 1 1 d . . .
O5 O 1.0416(3) 0.0637(3) 0.3633(2) 0.0455(8) Uani 1 1 d . . .
O6 O 1.6192(3) 0.5689(3) 0.3916(3) 0.0716(12) Uani 1 1 d . . .
O7 O 1.7264(3) 0.4257(3) 0.3123(3) 0.0624(10) Uani 1 1 d . . .
N1 N 0.7994(3) -0.0425(3) 0.4249(3) 0.0370(9) Uani 1 1 d . . .
H1 H 0.8514 -0.0584 0.4850 0.044 Uiso 1 1 calc R . .
N2 N 0.9594(4) 0.2500(3) 0.2121(3) 0.0378(9) Uani 1 1 d . . .
H2 H 0.8814 0.2907 0.2280 0.045 Uiso 1 1 calc R . .
N3 N 1.6043(4) 0.4748(4) 0.3362(3) 0.0453(10) Uani 1 1 d . . .
C1 C 0.6004(8) 0.2763(6) -0.0403(5) 0.094(2) Uani 1 1 d . . .
H1A H 0.4796 0.2635 -0.0326 0.113 Uiso 1 1 calc R . .
H1B H 0.6261 0.2463 -0.1151 0.113 Uiso 1 1 calc R . .
C2 C 0.6672(11) 0.4050(6) -0.0278(8) 0.148(4) Uani 1 1 d . . .
H2A H 0.6207 0.4468 -0.0865 0.223 Uiso 1 1 calc R . .
H2B H 0.7870 0.4170 -0.0338 0.223 Uiso 1 1 calc R . .
H2C H 0.6375 0.4349 0.0451 0.223 Uiso 1 1 calc R . .
C3 C 1.0732(5) 0.1920(4) -0.1187(4) 0.0539(13) Uani 1 1 d . . .
H3A H 1.0159 0.1423 -0.1805 0.065 Uiso 1 1 calc R . .
H3B H 1.1449 0.1456 -0.0793 0.065 Uiso 1 1 calc R . .
C4 C 1.1747(6) 0.2999(5) -0.1640(5) 0.0779(17) Uani 1 1 d . . .
H4A H 1.2550 0.2766 -0.2161 0.117 Uiso 1 1 calc R . .
H4B H 1.2324 0.3479 -0.1025 0.117 Uiso 1 1 calc R . .
H4C H 1.1028 0.3454 -0.2027 0.117 Uiso 1 1 calc R . .
C5 C 0.0361(5) -0.2957(4) 0.4570(4) 0.0557(13) Uani 1 1 d . . .
H5A H -0.0797 -0.3167 0.4347 0.083 Uiso 1 1 calc R . .
H5B H 0.0446 -0.2523 0.5289 0.083 Uiso 1 1 calc R . .
H5C H 0.0842 -0.3671 0.4638 0.083 Uiso 1 1 calc R . .
C6 C 0.2907(4) -0.1793(4) 0.3915(4) 0.0378(10) Uani 1 1 d . . .
C7 C 0.3681(4) -0.1082(4) 0.3098(4) 0.0395(11) Uani 1 1 d . . .
H7 H 0.3065 -0.0904 0.2475 0.047 Uiso 1 1 calc R . .
C8 C 0.5421(4) -0.0611(3) 0.3191(3) 0.0326(9) Uani 1 1 d . . .
C9 C 0.6308(4) 0.0115(3) 0.2357(3) 0.0334(9) Uani 1 1 d . . .
H9 H 0.5727 0.0307 0.1723 0.040 Uiso 1 1 calc R . .
C10 C 0.7980(4) 0.0535(3) 0.2462(3) 0.0309(9) Uani 1 1 d . . .
C11 C 0.8889(4) 0.0260(3) 0.3483(3) 0.0322(9) Uani 1 1 d . . .
C12 C 0.6302(4) -0.0894(3) 0.4148(3) 0.0314(9) Uani 1 1 d . . .
C13 C 0.5500(5) -0.1603(4) 0.4973(4) 0.0399(10) Uani 1 1 d . . .
H13 H 0.6101 -0.1770 0.5609 0.048 Uiso 1 1 calc R . .
C14 C 0.3812(5) -0.2068(4) 0.4865(4) 0.0403(11) Uani 1 1 d . . .
H14 H 0.3283 -0.2557 0.5417 0.048 Uiso 1 1 calc R . .
C15 C 0.9063(4) 0.1313(3) 0.1639(3) 0.0321(9) Uani 1 1 d . . .
H15 H 1.0083 0.0960 0.1546 0.039 Uiso 1 1 calc R . .
C16 C 1.1201(5) 0.3054(4) 0.2354(3) 0.0345(10) Uani 1 1 d . . .
C17 C 1.2611(5) 0.2522(4) 0.2077(4) 0.0411(11) Uani 1 1 d . . .
H17 H 1.2476 0.1789 0.1677 0.049 Uiso 1 1 calc R . .
C18 C 1.4184(5) 0.3093(4) 0.2400(4) 0.0441(11) Uani 1 1 d . . .
H18 H 1.5112 0.2742 0.2216 0.053 Uiso 1 1 calc R . .
C19 C 1.4405(4) 0.4171(4) 0.2989(4) 0.0374(10) Uani 1 1 d . . .
C20 C 1.3030(5) 0.4727(4) 0.3238(4) 0.0444(12) Uani 1 1 d . . .
H20 H 1.3178 0.5468 0.3622 0.053 Uiso 1 1 calc R . .
C21 C 1.1460(5) 0.4168(4) 0.2909(4) 0.0442(11) Uani 1 1 d . . .
H21 H 1.0545 0.4546 0.3062 0.053 Uiso 1 1 calc R . .


_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 1.455(3) . ?
P1 O2 1.575(3) . ?
P1 O3 1.568(3) . ?
P1 C15 1.824(4) . ?
O2 C1 1.450(6) . ?
O3 C3 1.455(5) . ?
O4 C5 1.427(5) . ?
O4 C6 1.370(4) . ?
O5 C11 1.248(4) . ?
O6 N3 1.219(4) . ?
O7 N3 1.241(4) . ?
N1 H1 0.8600 . ?
N1 C11 1.347(5) . ?
N1 C12 1.386(4) . ?
N2 H2 0.8600 . ?
N2 C15 1.438(4) . ?
N2 C16 1.369(4) . ?
N3 C19 1.436(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C1 C2 1.471(9) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C4 1.476(6) . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 H5A 0.9600 . ?
C5 H5B 0.9600 . ?
C5 H5C 0.9600 . ?
C6 C7 1.366(6) . ?
C6 C14 1.404(5) . ?
C7 H7 0.9300 . ?
C7 C8 1.423(5) . ?
C8 C9 1.425(5) . ?
C8 C12 1.402(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.361(5) . ?
C10 C11 1.472(5) . ?
C10 C15 1.519(5) . ?
C12 C13 1.381(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.384(5) . ?
C14 H14 0.9300 . ?
C15 H15 0.9800 . ?
C16 C17 1.411(5) . ?
C16 C21 1.386(5) . ?
C17 H17 0.9300 . ?
C17 C18 1.374(5) . ?
C18 H18 0.9300 . ?
C18 C19 1.368(5) . ?
C19 C20 1.394(5) . ?
C20 H20 0.9300 . ?
C20 C21 1.369(5) . ?
C21 H21 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 O2 117.21(16) . . ?
O1 P1 O3 114.53(18) . . ?
O1 P1 C15 115.07(17) . . ?
O2 P1 C15 100.79(17) . . ?
O3 P1 O2 102.59(16) . . ?
O3 P1 C15 104.77(17) . . ?
C1 O2 P1 123.2(3) . . ?
C3 O3 P1 122.8(3) . . ?
C6 O4 C5 118.6(3) . . ?
C11 N1 H1 117.3 . . ?
C11 N1 C12 125.4(3) . . ?
C12 N1 H1 117.3 . . ?
C15 N2 H2 116.3 . . ?
C16 N2 H2 116.3 . . ?
C16 N2 C15 127.4(3) . . ?
O6 N3 O7 122.1(3) . . ?
O6 N3 C19 119.4(4) . . ?
O7 N3 C19 118.5(4) . . ?
O2 C1 H1A 109.8 . . ?
O2 C1 H1B 109.8 . . ?
O2 C1 C2 109.4(5) . . ?
H1A C1 H1B 108.2 . . ?
C2 C1 H1A 109.8 . . ?
C2 C1 H1B 109.8 . . ?
C1 C2 H2A 109.5 . . ?
C1 C2 H2B 109.5 . . ?
C1 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O3 C3 H3A 110.0 . . ?
O3 C3 H3B 110.0 . . ?
O3 C3 C4 108.6(4) . . ?
H3A C3 H3B 108.4 . . ?
C4 C3 H3A 110.0 . . ?
C4 C3 H3B 110.0 . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4B 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O4 C5 H5A 109.5 . . ?
O4 C5 H5B 109.5 . . ?
O4 C5 H5C 109.5 . . ?
H5A C5 H5B 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
O4 C6 C14 123.2(4) . . ?
C7 C6 O4 116.2(4) . . ?
C7 C6 C14 120.6(3) . . ?
C6 C7 H7 119.7 . . ?
C6 C7 C8 120.7(4) . . ?
C8 C7 H7 119.7 . . ?
C7 C8 C9 123.4(4) . . ?
C12 C8 C7 117.8(4) . . ?
C12 C8 C9 118.7(3) . . ?
C8 C9 H9 119.0 . . ?
C10 C9 C8 121.9(4) . . ?
C10 C9 H9 119.0 . . ?
C9 C10 C11 119.0(4) . . ?
C9 C10 C15 127.0(3) . . ?
C11 C10 C15 114.0(3) . . ?
O5 C11 N1 121.4(3) . . ?
O5 C11 C10 121.8(4) . . ?
N1 C11 C10 116.8(3) . . ?
N1 C12 C8 118.1(4) . . ?
C13 C12 N1 121.1(3) . . ?
C13 C12 C8 120.9(3) . . ?
C12 C13 H13 119.7 . . ?
C12 C13 C14 120.7(4) . . ?
C14 C13 H13 119.7 . . ?
C6 C14 H14 120.3 . . ?
C13 C14 C6 119.3(4) . . ?
C13 C14 H14 120.3 . . ?
P1 C15 H15 106.1 . . ?
N2 C15 P1 110.6(3) . . ?
N2 C15 C10 111.0(3) . . ?
N2 C15 H15 106.1 . . ?
C10 C15 P1 116.3(2) . . ?
C10 C15 H15 106.1 . . ?
N2 C16 C17 122.5(3) . . ?
N2 C16 C21 119.0(3) . . ?
C21 C16 C17 118.5(3) . . ?
C16 C17 H17 120.2 . . ?
C18 C17 C16 119.6(4) . . ?
C18 C17 H17 120.2 . . ?
C17 C18 H18 119.5 . . ?
C19 C18 C17 121.0(4) . . ?
C19 C18 H18 119.5 . . ?
C18 C19 N3 121.0(4) . . ?
C18 C19 C20 120.1(3) . . ?
C20 C19 N3 118.8(4) . . ?
C19 C20 H20 120.4 . . ?
C21 C20 C19 119.2(4) . . ?
C21 C20 H20 120.4 . . ?
C16 C21 H21 119.2 . . ?
C20 C21 C16 121.6(4) . . ?
C20 C21 H21 119.2 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_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 O2 C1 C2 -103.1(5) . . . . ?
P1 O3 C3 C4 178.5(3) . . . . ?
O1 P1 O2 C1 -74.8(4) . . . . ?
O1 P1 O3 C3 -27.0(4) . . . . ?
O1 P1 C15 N2 175.7(2) . . . . ?
O1 P1 C15 C10 -56.5(3) . . . . ?
O2 P1 O3 C3 -155.1(3) . . . . ?
O2 P1 C15 N2 -57.2(3) . . . . ?
O2 P1 C15 C10 70.5(3) . . . . ?
O3 P1 O2 C1 51.6(4) . . . . ?
O3 P1 C15 N2 49.0(3) . . . . ?
O3 P1 C15 C10 176.8(3) . . . . ?
O4 C6 C7 C8 -178.4(3) . . . . ?
O4 C6 C14 C13 179.1(4) . . . . ?
O6 N3 C19 C18 -177.7(4) . . . . ?
O6 N3 C19 C20 2.3(6) . . . . ?
O7 N3 C19 C18 1.1(6) . . . . ?
O7 N3 C19 C20 -179.0(4) . . . . ?
N1 C12 C13 C14 -180.0(4) . . . . ?
N2 C16 C17 C18 -175.8(4) . . . . ?
N2 C16 C21 C20 175.2(4) . . . . ?
N3 C19 C20 C21 -178.4(4) . . . . ?
C5 O4 C6 C7 -178.9(4) . . . . ?
C5 O4 C6 C14 2.4(6) . . . . ?
C6 C7 C8 C9 178.7(4) . . . . ?
C6 C7 C8 C12 -0.4(6) . . . . ?
C7 C6 C14 C13 0.5(6) . . . . ?
C7 C8 C9 C10 -178.8(4) . . . . ?
C7 C8 C12 N1 -179.2(3) . . . . ?
C7 C8 C12 C13 -0.3(6) . . . . ?
C8 C9 C10 C11 -1.8(6) . . . . ?
C8 C9 C10 C15 -179.9(3) . . . . ?
C8 C12 C13 C14 1.1(6) . . . . ?
C9 C8 C12 N1 1.6(5) . . . . ?
C9 C8 C12 C13 -179.4(3) . . . . ?
C9 C10 C11 O5 -178.8(4) . . . . ?
C9 C10 C11 N1 1.4(5) . . . . ?
C9 C10 C15 P1 -16.9(5) . . . . ?
C9 C10 C15 N2 110.6(4) . . . . ?
C11 N1 C12 C8 -2.1(6) . . . . ?
C11 N1 C12 C13 179.0(4) . . . . ?
C11 C10 C15 P1 164.9(3) . . . . ?
C11 C10 C15 N2 -67.5(4) . . . . ?
C12 N1 C11 O5 -179.2(4) . . . . ?
C12 N1 C11 C10 0.5(5) . . . . ?
C12 C8 C9 C10 0.3(6) . . . . ?
C12 C13 C14 C6 -1.2(6) . . . . ?
C14 C6 C7 C8 0.3(6) . . . . ?
C15 P1 O2 C1 159.6(4) . . . . ?
C15 P1 O3 C3 100.0(3) . . . . ?
C15 N2 C16 C17 3.8(6) . . . . ?
C15 N2 C16 C21 -174.6(4) . . . . ?
C15 C10 C11 O5 -0.5(5) . . . . ?
C15 C10 C11 N1 179.7(3) . . . . ?
C16 N2 C15 P1 -111.7(4) . . . . ?
C16 N2 C15 C10 117.7(4) . . . . ?
C16 C17 C18 C19 0.0(7) . . . . ?
C17 C16 C21 C20 -3.3(7) . . . . ?
C17 C18 C19 N3 177.8(4) . . . . ?
C17 C18 C19 C20 -2.1(7) . . . . ?
C18 C19 C20 C21 1.5(7) . . . . ?
C19 C20 C21 C16 1.2(7) . . . . ?
C21 C16 C17 C18 2.6(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_20151208-czf-zy-yyc-75
_database_code_depnum_ccdc_archive 'CCDC 1531268'
_audit_update_record             
;
2017-02-06 deposited with the CCDC.
2017-03-30 downloaded from the CCDC.
;
_audit_creation_date             2015-12-15
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C22 H26 N2 O5 P'
_chemical_formula_sum            'C23 H26 N O5 P'
_chemical_formula_weight         427.42
_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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.405(2)
_cell_length_b                   16.660(3)
_cell_length_c                   16.156(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.29(2)
_cell_angle_gamma                90.00
_cell_volume                     2232.5(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    ?
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      ?
_cell_measurement_theta_min      ?
_exptl_absorpt_coefficient_mu    0.156
_exptl_absorpt_correction_T_max  0.9845
_exptl_absorpt_correction_T_min  0.9531
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.10
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_unetI/netI     0.1002
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4355
_diffrn_reflns_theta_full        26.37
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.47
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.701
_diffrn_measured_fraction_theta_max 0.701
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1428
_reflns_number_total             3201
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.190
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     275
_refine_ls_number_reflns         3201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1627
_refine_ls_R_factor_gt           0.0725
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.004
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0670P)²+0.7543P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1538
_refine_ls_wR_factor_ref         0.2195
_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. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.9076(2) 0.74629(11) 1.10281(14) 0.0810(7) Uani 1 1 d . . .
O1 O 1.1308(4) 0.6037(2) 0.2654(3) 0.0680(12) Uani 1 1 d . . .
O2 O 0.6026(4) 0.5314(2) 0.5992(3) 0.0630(11) Uani 1 1 d . . .
H2 H 0.6452 0.5141 0.6449 0.095 Uiso 1 1 calc R . .
O3 O 0.8381(5) 0.8116(2) 1.0481(3) 0.0926(16) Uani 1 1 d . . .
O4 O 0.7945(6) 0.6707(3) 1.1042(4) 0.1063(18) Uani 1 1 d . . .
O5 O 0.9592(7) 0.7685(3) 1.1985(3) 0.134(2) Uani 1 1 d . . .
N1 N 1.0006(5) 0.6476(2) 0.7216(3) 0.0529(12) Uani 1 1 d . . .
C1 C 1.2810(7) 0.6432(4) 0.2964(4) 0.081(2) Uani 1 1 d . . .
H1A H 1.3427 0.6489 0.2516 0.122 Uiso 1 1 calc R . .
H1B H 1.3408 0.6118 0.3407 0.122 Uiso 1 1 calc R . .
H1C H 1.2597 0.6953 0.3175 0.122 Uiso 1 1 calc R . .
C2 C 1.0271(6) 0.5937(3) 0.3217(4) 0.0526(15) Uani 1 1 d . . .
C3 C 0.8787(6) 0.5592(3) 0.2867(4) 0.0565(15) Uani 1 1 d . . .
H3 H 0.8580 0.5476 0.2297 0.068 Uiso 1 1 calc R . .
C4 C 0.7647(6) 0.5428(3) 0.3358(4) 0.0520(14) Uani 1 1 d . . .
H4 H 0.6655 0.5217 0.3119 0.062 Uiso 1 1 calc R . .
C5 C 0.7975(6) 0.5578(3) 0.4222(4) 0.0442(13) Uani 1 1 d . . .
N N 0.6865(4) 0.5387(2) 0.4741(3) 0.0485(12) Uani 1 1 d . . .
H H 0.5969 0.5171 0.4516 0.058 Uiso 1 1 calc R . .
C7 C 0.7104(6) 0.5519(3) 0.5570(4) 0.0481(14) Uani 1 1 d . . .
C8 C 0.8576(6) 0.5916(3) 0.5943(4) 0.0450(14) Uani 1 1 d . . .
C9 C 0.9688(6) 0.6096(3) 0.5452(4) 0.0484(14) Uani 1 1 d . . .
H9 H 1.0654 0.6331 0.5696 0.058 Uiso 1 1 calc R . .
C10 C 0.9427(5) 0.5937(2) 0.4578(4) 0.0417(13) Uani 1 1 d . . .
C11 C 1.0580(6) 0.6108(3) 0.4054(4) 0.0490(14) Uani 1 1 d . . .
H11 H 1.1560 0.6339 0.4282 0.059 Uiso 1 1 calc R . .
C12 C 0.8840(6) 0.6073(3) 0.6841(4) 0.0527(15) Uani 1 1 d . . .
H12 H 0.8106 0.5862 0.7156 0.063 Uiso 1 1 calc R . .
C13 C 1.0214(6) 0.6556(3) 0.8095(4) 0.0552(16) Uani 1 1 d . . .
C14 C 0.9812(7) 0.5984(3) 0.8647(4) 0.0636(17) Uani 1 1 d . . .
H14 H 0.9386 0.5495 0.8441 0.076 Uiso 1 1 calc R . .
C15 C 1.0036(7) 0.6130(3) 0.9491(4) 0.0677(17) Uani 1 1 d . . .
H15 H 0.9745 0.5739 0.9848 0.081 Uiso 1 1 calc R . .
C16 C 1.0683(7) 0.6846(4) 0.9828(4) 0.0634(17) Uani 1 1 d . . .
C17 C 1.1132(7) 0.7395(3) 0.9277(4) 0.0666(17) Uani 1 1 d . . .
H17 H 1.1592 0.7876 0.9486 0.080 Uiso 1 1 calc R . .
C18 C 1.0928(6) 0.7263(3) 0.8432(4) 0.0650(17) Uani 1 1 d . . .
H18 H 1.1267 0.7646 0.8080 0.078 Uiso 1 1 calc R . .
C19 C 1.0841(7) 0.7020(3) 1.0768(4) 0.0718(18) Uani 1 1 d . . .
H19A H 1.1746 0.7378 1.0934 0.086 Uiso 1 1 calc R . .
H19B H 1.1059 0.6523 1.1078 0.086 Uiso 1 1 calc R . .
C20 C 0.6229(16) 0.6745(6) 1.0819(8) 0.196(6) Uani 1 1 d . . .
H20A H 0.5810 0.7068 1.1234 0.235 Uiso 1 1 calc R . .
H20B H 0.5974 0.7021 1.0285 0.235 Uiso 1 1 calc R . .
C21 C 0.5462(12) 0.6047(8) 1.0756(9) 0.210(6) Uani 1 1 d . . .
H21A H 0.4415 0.6113 1.0424 0.315 Uiso 1 1 calc R . .
H21B H 0.5347 0.5861 1.1305 0.315 Uiso 1 1 calc R . .
H21C H 0.6069 0.5663 1.0492 0.315 Uiso 1 1 calc R . .
C22 C 0.9254(9) 0.8384(5) 1.2335(6) 0.106(3) Uani 1 1 d . . .
H22A H 0.8096 0.8418 1.2316 0.127 Uiso 1 1 calc R . .
H22B H 0.9569 0.8820 1.1999 0.127 Uiso 1 1 calc R . .
C23 C 1.0013(10) 0.8497(5) 1.3178(6) 0.126(3) Uani 1 1 d . . .
H23A H 1.1123 0.8338 1.3233 0.189 Uiso 1 1 calc R . .
H23B H 0.9479 0.8175 1.3543 0.189 Uiso 1 1 calc R . .
H23C H 0.9950 0.9052 1.3326 0.189 Uiso 1 1 calc R . .


_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 O3 1.463(4) . ?
P1 O4 1.580(5) . ?
P1 O5 1.581(5) . ?
P1 C19 1.767(6) . ?
O1 C1 1.440(6) . ?
O1 C2 1.367(6) . ?
O2 H2 0.8200 . ?
O2 C7 1.266(5) . ?
O4 C20 1.431(11) . ?
O5 C22 1.345(7) . ?
N1 C12 1.261(6) . ?
N1 C13 1.409(7) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.406(7) . ?
C2 C11 1.365(8) . ?
C3 H3 0.9300 . ?
C3 C4 1.367(6) . ?
C4 H4 0.9300 . ?
C4 C5 1.401(7) . ?
C5 N 1.388(6) . ?
C5 C10 1.397(6) . ?
N H 0.8600 . ?
N C7 1.340(7) . ?
C7 C8 1.446(7) . ?
C8 C9 1.353(6) . ?
C8 C12 1.455(7) . ?
C9 H9 0.9300 . ?
C9 C10 1.419(7) . ?
C10 C11 1.414(7) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.383(7) . ?
C13 C18 1.391(7) . ?
C14 H14 0.9300 . ?
C14 C15 1.369(8) . ?
C15 H15 0.9300 . ?
C15 C16 1.385(8) . ?
C16 C17 1.371(8) . ?
C16 C19 1.531(8) . ?
C17 H17 0.9300 . ?
C17 C18 1.366(8) . ?
C18 H18 0.9300 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C20 C21 1.324(11) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C22 C23 1.419(10) . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

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
O3 P1 O4 114.8(3) . . ?
O3 P1 O5 115.9(3) . . ?
O3 P1 C19 115.8(3) . . ?
O4 P1 O5 104.1(3) . . ?
O4 P1 C19 101.6(3) . . ?
O5 P1 C19 102.8(3) . . ?
C2 O1 C1 116.2(5) . . ?
C7 O2 H2 109.5 . . ?
C20 O4 P1 123.1(6) . . ?
C22 O5 P1 124.8(5) . . ?
C12 N1 C13 119.7(5) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 113.7(6) . . ?
O1 C2 C11 126.4(5) . . ?
C11 C2 C3 119.8(5) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 C2 120.5(6) . . ?
C4 C3 H3 119.7 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 119.9(5) . . ?
C5 C4 H4 120.0 . . ?
N C5 C4 121.2(5) . . ?
N C5 C10 118.5(5) . . ?
C10 C5 C4 120.3(5) . . ?
C5 N H 118.0 . . ?
C7 N C5 124.0(5) . . ?
C7 N H 118.0 . . ?
O2 C7 N 119.3(5) . . ?
O2 C7 C8 122.5(6) . . ?
N C7 C8 118.2(5) . . ?
C7 C8 C12 118.7(5) . . ?
C9 C8 C7 118.8(6) . . ?
C9 C8 C12 122.4(5) . . ?
C8 C9 H9 118.9 . . ?
C8 C9 C10 122.2(5) . . ?
C10 C9 H9 118.9 . . ?
C5 C10 C9 118.2(5) . . ?
C5 C10 C11 118.5(5) . . ?
C11 C10 C9 123.2(5) . . ?
C2 C11 C10 120.8(5) . . ?
C2 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
N1 C12 C8 123.9(5) . . ?
N1 C12 H12 118.1 . . ?
C8 C12 H12 118.1 . . ?
C14 C13 N1 125.5(5) . . ?
C14 C13 C18 117.7(6) . . ?
C18 C13 N1 116.7(5) . . ?
C13 C14 H14 119.6 . . ?
C15 C14 C13 120.7(5) . . ?
C15 C14 H14 119.6 . . ?
C14 C15 H15 119.1 . . ?
C14 C15 C16 121.8(6) . . ?
C16 C15 H15 119.1 . . ?
C15 C16 C19 121.2(6) . . ?
C17 C16 C15 116.8(6) . . ?
C17 C16 C19 121.9(6) . . ?
C16 C17 H17 118.7 . . ?
C18 C17 C16 122.5(6) . . ?
C18 C17 H17 118.7 . . ?
C13 C18 H18 119.9 . . ?
C17 C18 C13 120.3(6) . . ?
C17 C18 H18 119.9 . . ?
P1 C19 H19A 109.2 . . ?
P1 C19 H19B 109.2 . . ?
C16 C19 P1 112.0(4) . . ?
C16 C19 H19A 109.2 . . ?
C16 C19 H19B 109.2 . . ?
H19A C19 H19B 107.9 . . ?
O4 C20 H20A 108.3 . . ?
O4 C20 H20B 108.3 . . ?
H20A C20 H20B 107.4 . . ?
C21 C20 O4 116.1(9) . . ?
C21 C20 H20A 108.3 . . ?
C21 C20 H20B 108.3 . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
O5 C22 H22A 108.5 . . ?
O5 C22 H22B 108.5 . . ?
O5 C22 C23 115.2(8) . . ?
H22A C22 H22B 107.5 . . ?
C23 C22 H22A 108.5 . . ?
C23 C22 H22B 108.5 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_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 O4 C20 C21 171.5(9) . . . . ?
P1 O5 C22 C23 -172.1(7) . . . . ?
O1 C2 C3 C4 177.6(4) . . . . ?
O1 C2 C11 C10 -176.7(4) . . . . ?
O2 C7 C8 C9 178.3(4) . . . . ?
O2 C7 C8 C12 1.2(7) . . . . ?
O3 P1 O4 C20 -22.7(9) . . . . ?
O3 P1 O5 C22 8.8(8) . . . . ?
O3 P1 C19 C16 -45.7(5) . . . . ?
O4 P1 O5 C22 -118.2(7) . . . . ?
O4 P1 C19 C16 79.3(5) . . . . ?
O5 P1 O4 C20 105.0(8) . . . . ?
O5 P1 C19 C16 -173.1(4) . . . . ?
N1 C13 C14 C15 -178.7(5) . . . . ?
N1 C13 C18 C17 178.2(5) . . . . ?
C1 O1 C2 C3 176.3(4) . . . . ?
C1 O1 C2 C11 -6.3(8) . . . . ?
C2 C3 C4 C5 -2.1(8) . . . . ?
C3 C2 C11 C10 0.5(7) . . . . ?
C3 C4 C5 N -177.4(4) . . . . ?
C3 C4 C5 C10 3.7(7) . . . . ?
C4 C5 N C7 -179.6(4) . . . . ?
C4 C5 C10 C9 178.4(4) . . . . ?
C4 C5 C10 C11 -3.1(7) . . . . ?
C5 N C7 O2 -179.1(4) . . . . ?
C5 N C7 C8 2.8(7) . . . . ?
C5 C10 C11 C2 1.1(7) . . . . ?
N C5 C10 C9 -0.5(6) . . . . ?
N C5 C10 C11 177.9(4) . . . . ?
N C7 C8 C9 -3.8(7) . . . . ?
N C7 C8 C12 179.2(4) . . . . ?
C7 C8 C9 C10 2.7(7) . . . . ?
C7 C8 C12 N1 -173.5(4) . . . . ?
C8 C9 C10 C5 -0.5(7) . . . . ?
C8 C9 C10 C11 -178.9(4) . . . . ?
C9 C8 C12 N1 9.6(8) . . . . ?
C9 C10 C11 C2 179.5(4) . . . . ?
C10 C5 N C7 -0.7(7) . . . . ?
C11 C2 C3 C4 0.1(8) . . . . ?
C12 N1 C13 C14 32.3(8) . . . . ?
C12 N1 C13 C18 -149.6(5) . . . . ?
C12 C8 C9 C10 179.6(4) . . . . ?
C13 N1 C12 C8 -176.3(4) . . . . ?
C13 C14 C15 C16 -0.7(9) . . . . ?
C14 C13 C18 C17 -3.6(8) . . . . ?
C14 C15 C16 C17 -1.7(9) . . . . ?
C14 C15 C16 C19 176.6(5) . . . . ?
C15 C16 C17 C18 1.4(9) . . . . ?
C15 C16 C19 P1 -87.6(6) . . . . ?
C16 C17 C18 C13 1.2(9) . . . . ?
C17 C16 C19 P1 90.6(6) . . . . ?
C18 C13 C14 C15 3.3(8) . . . . ?
C19 P1 O4 C20 -148.4(8) . . . . ?
C19 P1 O5 C22 136.2(7) . . . . ?
C19 C16 C17 C18 -176.8(5) . . . . ?

