# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# 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_pnk16f1
_database_code_depnum_ccdc_archive 'CCDC 1550956'
_audit_update_record             
;
2017-05-18 deposited with the CCDC.
2017-09-14 downloaded from the CCDC.
;
_audit_creation_date             2015-12-15
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_shelxl_version_number           2014/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H37 N2 O5 P'
_chemical_formula_sum            'C20 H37 N2 O5 P'
_chemical_formula_weight         416.48
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c20 h37 n2 o5 p1'
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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.3358(4)
_cell_length_b                   8.9190(3)
_cell_length_c                   19.7702(8)
_cell_angle_alpha                90
_cell_angle_beta                 95.598(3)
_cell_angle_gamma                90
_cell_volume                     2340.28(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4982
_cell_measurement_temperature    293
_cell_measurement_theta_max      25.5260
_cell_measurement_theta_min      3.8680
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0272
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.874
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            15918
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.874
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.705
_diffrn_reflns_theta_min         3.532
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.874
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -31.00   -5.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9721   77.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  2 omega   23.00   78.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -      -14.9721   77.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
  3 omega    4.00   86.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0658   77.0000    0.0000 82

#__ type_ start__ end____ width___ exp.time_
  4 omega  -16.00  112.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0658   77.0000  120.0000 128

#__ type_ start__ end____ width___ exp.time_
  5 omega  -25.00   71.00   1.0000   20.0000
omega____ theta____ kappa____ phi______ frames
    -       16.0658   77.0000  -90.0000 96
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0348580000
_diffrn_orient_matrix_UB_12      0.0598160000
_diffrn_orient_matrix_UB_13      -0.0010446000
_diffrn_orient_matrix_UB_21      -0.0402722000
_diffrn_orient_matrix_UB_22      0.0499987000
_diffrn_orient_matrix_UB_23      -0.0096034000
_diffrn_orient_matrix_UB_31      -0.0046640000
_diffrn_orient_matrix_UB_32      0.0156396000
_diffrn_orient_matrix_UB_33      0.0347210000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3474
_reflns_number_total             4783
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.66
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.614
_refine_diff_density_min         -0.483
_refine_diff_density_rms         0.046
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4783
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0621
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0645P)²+1.7132P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1501
_refine_ls_wR_factor_ref         0.1665
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C17(H17A,H17B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C11(H11A,H11B,H11C), C14(H14A,H14B,
 H14C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C20(H20A,
 H20B,H20C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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 0.29520(5) 0.27607(8) 0.29128(3) 0.0450(2) Uani 1 1 d . . . . .
O1 O 0.13434(11) 0.23336(18) 0.36551(8) 0.0390(4) Uani 1 1 d . . . . .
O2 O 0.08494(17) 0.5362(3) 0.33018(15) 0.0807(7) Uani 1 1 d . . . . .
H2 H 0.1351 0.5177 0.3108 0.121 Uiso 1 1 calc GR . . . .
O3 O 0.26118(16) 0.4324(2) 0.28486(10) 0.0644(6) Uani 1 1 d . . . . .
O4 O 0.23321(14) 0.1660(2) 0.24255(9) 0.0566(5) Uani 1 1 d . . . . .
O5 O 0.40591(14) 0.2518(3) 0.27160(10) 0.0652(6) Uani 1 1 d . . . . .
N1 N 0.21612(14) 0.1562(2) 0.40602(10) 0.0389(5) Uani 1 1 d . . . . .
N2 N -0.09296(17) 0.3609(3) 0.43265(12) 0.0544(6) Uani 1 1 d . . . . .
C1 C 0.07647(18) 0.3265(3) 0.40731(13) 0.0436(6) Uani 1 1 d . . . . .
H1 H 0.0934 0.2998 0.4551 0.052 Uiso 1 1 calc R . . . .
C2 C -0.03504(17) 0.3000(3) 0.38857(12) 0.0399(5) Uani 1 1 d . . . . .
C3 C -0.07429(19) 0.2263(3) 0.33113(14) 0.0510(7) Uani 1 1 d . . . . .
H3 H -0.0318 0.1853 0.3014 0.061 Uiso 1 1 calc R . . . .
C4 C -0.1773(2) 0.2135(4) 0.31782(16) 0.0609(8) Uani 1 1 d . . . . .
H4 H -0.2052 0.1641 0.2791 0.073 Uiso 1 1 calc R . . . .
C5 C -0.2377(2) 0.2747(4) 0.36258(18) 0.0651(8) Uani 1 1 d . . . . .
H5 H -0.3075 0.2670 0.3553 0.078 Uiso 1 1 calc R . . . .
C6 C -0.1927(2) 0.3474(4) 0.41824(17) 0.0659(9) Uani 1 1 d . . . . .
H6 H -0.2341 0.3903 0.4481 0.079 Uiso 1 1 calc R . . . .
C7 C 0.1010(2) 0.4910(3) 0.39741(19) 0.0664(9) Uani 1 1 d . . . . .
H7A H 0.0597 0.5515 0.4246 0.080 Uiso 1 1 calc R . . . .
H7B H 0.1710 0.5086 0.4137 0.080 Uiso 1 1 calc R . . . .
C8 C 0.1886(2) -0.0074(3) 0.40739(14) 0.0509(7) Uani 1 1 d . . . . .
C9 C 0.0969(2) -0.0204(4) 0.44751(17) 0.0644(8) Uani 1 1 d . . . . .
H9A H 0.1105 0.0296 0.4904 0.097 Uiso 1 1 calc GR . . . .
H9B H 0.0828 -0.1242 0.4551 0.097 Uiso 1 1 calc GR . . . .
H9C H 0.0398 0.0254 0.4223 0.097 Uiso 1 1 calc GR . . . .
C10 C 0.1659(3) -0.0783(3) 0.33762(18) 0.0750(10) Uani 1 1 d . . . . .
H10A H 0.1104 -0.0267 0.3132 0.112 Uiso 1 1 calc GR . . . .
H10B H 0.1486 -0.1819 0.3427 0.112 Uiso 1 1 calc GR . . . .
H10C H 0.2242 -0.0709 0.3129 0.112 Uiso 1 1 calc GR . . . .
C11 C 0.2747(2) -0.0931(4) 0.4479(2) 0.0768(10) Uani 1 1 d . . . . .
H11A H 0.3352 -0.0834 0.4256 0.115 Uiso 1 1 calc GR . . . .
H11B H 0.2571 -0.1971 0.4506 0.115 Uiso 1 1 calc GR . . . .
H11C H 0.2858 -0.0521 0.4930 0.115 Uiso 1 1 calc GR . . . .
C12 C 0.31142(17) 0.1920(3) 0.37637(12) 0.0412(6) Uani 1 1 d . . . . .
H12 H 0.3429 0.0944 0.3699 0.049 Uiso 1 1 calc R . . . .
C13 C 0.3895(2) 0.2790(4) 0.42852(15) 0.0562(7) Uani 1 1 d . . . . .
C14 C 0.3667(4) 0.2568(8) 0.4995(2) 0.164(3) Uani 1 1 d . . . . .
H14A H 0.3820 0.1554 0.5131 0.246 Uiso 1 1 calc GR . . . .
H14B H 0.2966 0.2763 0.5029 0.246 Uiso 1 1 calc GR . . . .
H14C H 0.4068 0.3244 0.5287 0.246 Uiso 1 1 calc GR . . . .
C15 C 0.3926(5) 0.4468(6) 0.4155(3) 0.180(3) Uani 1 1 d . . . . .
H15A H 0.3279 0.4897 0.4209 0.270 Uiso 1 1 calc GR . . . .
H15B H 0.4094 0.4645 0.3700 0.270 Uiso 1 1 calc GR . . . .
H15C H 0.4426 0.4922 0.4473 0.270 Uiso 1 1 calc GR . . . .
C16 C 0.4928(3) 0.2223(8) 0.4221(3) 0.153(3) Uani 1 1 d . . . . .
H16A H 0.5379 0.2602 0.4590 0.230 Uiso 1 1 calc GR . . . .
H16B H 0.5147 0.2554 0.3798 0.230 Uiso 1 1 calc GR . . . .
H16C H 0.4926 0.1147 0.4235 0.230 Uiso 1 1 calc GR . . . .
C17 C 0.1377(2) 0.2030(5) 0.20432(16) 0.0733(10) Uani 1 1 d . . . . .
H17A H 0.1038 0.2795 0.2285 0.088 Uiso 1 1 calc R . . . .
H17B H 0.0951 0.1147 0.2008 0.088 Uiso 1 1 calc R . . . .
C18 C 0.1522(3) 0.2577(5) 0.13556(17) 0.0815(11) Uani 1 1 d . . . . .
H18A H 0.1869 0.3521 0.1388 0.122 Uiso 1 1 calc GR . . . .
H18B H 0.0878 0.2701 0.1099 0.122 Uiso 1 1 calc GR . . . .
H18C H 0.1915 0.1863 0.1131 0.122 Uiso 1 1 calc GR . . . .
C19 C 0.4334(3) 0.2949(7) 0.2058(2) 0.1219(19) Uani 1 1 d . . . . .
H19A H 0.4019 0.2268 0.1718 0.146 Uiso 1 1 calc R . . . .
H19B H 0.4078 0.3949 0.1951 0.146 Uiso 1 1 calc R . . . .
C20 C 0.5381(4) 0.2936(8) 0.2025(3) 0.148(2) Uani 1 1 d . . . . .
H20A H 0.5526 0.3129 0.1567 0.223 Uiso 1 1 calc GR . . . .
H20B H 0.5646 0.1972 0.2166 0.223 Uiso 1 1 calc GR . . . .
H20C H 0.5689 0.3697 0.2320 0.223 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 O3 1.468(2) . ?
P1 O4 1.556(2) . ?
P1 O5 1.578(2) . ?
P1 C12 1.835(3) . ?
O1 N1 1.461(2) . ?
O1 C1 1.447(3) . ?
O2 H2 0.8200 . ?
O2 C7 1.386(4) . ?
O4 C17 1.454(3) . ?
O5 C19 1.439(4) . ?
N1 C8 1.506(3) . ?
N1 C12 1.485(3) . ?
N2 C2 1.335(3) . ?
N2 C6 1.338(4) . ?
C1 H1 0.9800 . ?
C1 C2 1.515(3) . ?
C1 C7 1.520(4) . ?
C2 C3 1.371(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.378(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.367(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.365(5) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.525(4) . ?
C8 C10 1.521(4) . ?
C8 C11 1.538(4) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12 0.9800 . ?
C12 C13 1.594(4) . ?
C13 C14 1.478(5) . ?
C13 C15 1.520(6) . ?
C13 C16 1.484(5) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.475(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.405(6) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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 113.88(12) . . ?
O3 P1 O5 113.45(12) . . ?
O3 P1 C12 118.38(12) . . ?
O4 P1 O5 102.35(12) . . ?
O4 P1 C12 108.53(11) . . ?
O5 P1 C12 98.07(11) . . ?
C1 O1 N1 111.62(16) . . ?
C7 O2 H2 109.5 . . ?
C17 O4 P1 124.3(2) . . ?
C19 O5 P1 120.9(2) . . ?
O1 N1 C8 107.23(17) . . ?
O1 N1 C12 107.73(16) . . ?
C12 N1 C8 115.74(19) . . ?
C2 N2 C6 116.8(2) . . ?
O1 C1 H1 109.0 . . ?
O1 C1 C2 109.67(19) . . ?
O1 C1 C7 110.3(2) . . ?
C2 C1 H1 109.0 . . ?
C2 C1 C7 109.7(2) . . ?
C7 C1 H1 109.0 . . ?
N2 C2 C1 113.2(2) . . ?
N2 C2 C3 122.5(2) . . ?
C3 C2 C1 124.3(2) . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.4(3) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 120.6 . . ?
C5 C4 C3 118.9(3) . . ?
C5 C4 H4 120.6 . . ?
C4 C5 H5 121.0 . . ?
C6 C5 C4 118.1(3) . . ?
C6 C5 H5 121.0 . . ?
N2 C6 C5 124.4(3) . . ?
N2 C6 H6 117.8 . . ?
C5 C6 H6 117.8 . . ?
O2 C7 C1 112.9(2) . . ?
O2 C7 H7A 109.0 . . ?
O2 C7 H7B 109.0 . . ?
C1 C7 H7A 109.0 . . ?
C1 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
N1 C8 C9 107.0(2) . . ?
N1 C8 C10 114.4(2) . . ?
N1 C8 C11 108.7(2) . . ?
C9 C8 C11 106.7(2) . . ?
C10 C8 C9 109.9(2) . . ?
C10 C8 C11 109.8(3) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
P1 C12 H12 104.8 . . ?
N1 C12 P1 114.87(16) . . ?
N1 C12 H12 104.8 . . ?
N1 C12 C13 112.3(2) . . ?
C13 C12 P1 113.89(17) . . ?
C13 C12 H12 104.8 . . ?
C14 C13 C12 111.6(3) . . ?
C14 C13 C15 107.7(4) . . ?
C14 C13 C16 108.3(4) . . ?
C15 C13 C12 113.4(3) . . ?
C16 C13 C12 109.4(3) . . ?
C16 C13 C15 106.2(4) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C17 H17A 109.3 . . ?
O4 C17 H17B 109.3 . . ?
O4 C17 C18 111.5(3) . . ?
H17A C17 H17B 108.0 . . ?
C18 C17 H17A 109.3 . . ?
C18 C17 H17B 109.3 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O5 C19 H19A 109.1 . . ?
O5 C19 H19B 109.1 . . ?
H19A C19 H19B 107.9 . . ?
C20 C19 O5 112.4(4) . . ?
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 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_jp297rrss
_database_code_depnum_ccdc_archive 'CCDC 1550955'
_audit_update_record             
;
2017-05-18 deposited with the CCDC.
2017-09-14 downloaded from the CCDC.
;
_audit_creation_date             2016-09-12
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.08.31 svn.r3340 for OlexSys, GUI svn.r5221)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H37 N2 O5 P'
_chemical_formula_sum            'C20 H37 N2 O5 P'
_chemical_formula_weight         416.48
_chemical_melting_point          ?
_chemical_oxdiff_formula         'c20 h37 n2 o5 p1'
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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.4884(6)
_cell_length_b                   12.0955(4)
_cell_length_c                   14.1006(6)
_cell_angle_alpha                90
_cell_angle_beta                 108.748(5)
_cell_angle_gamma                90
_cell_volume                     2339.94(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6274
_cell_measurement_temperature    293
_cell_measurement_theta_max      27.1280
_cell_measurement_theta_min      4.1600
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.148
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.77700
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.182
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_unetI/netI     0.0274
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.859
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            18820
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.859
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.383
_diffrn_reflns_theta_min         3.369
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.859
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -5.00  39.00   1.00   25.00    --   -8.76  38.00-180.00   44
  2  ω     -6.00  64.00   1.00   25.00    --   -8.76  38.00   0.00   70
  3  ω    -18.00  88.00   1.00   25.00    --    9.46  77.00  30.00  106
  4  ω      1.00  48.00   1.00   25.00    --    9.46 -99.00 -30.00   47
  5  ω    -20.00  50.00   1.00   25.00    --    9.46 -99.00-120.00   70
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0264864000
_diffrn_orient_matrix_UB_12      -0.0431917000
_diffrn_orient_matrix_UB_13      0.0134536000
_diffrn_orient_matrix_UB_21      -0.0272044000
_diffrn_orient_matrix_UB_22      0.0396371000
_diffrn_orient_matrix_UB_23      0.0169754000
_diffrn_orient_matrix_UB_31      -0.0350682000
_diffrn_orient_matrix_UB_32      0.0018821000
_diffrn_orient_matrix_UB_33      -0.0485135000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3760
_reflns_number_total             5038
_reflns_odcompleteness_completeness 99.64
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.66
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_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    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.282
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         5038
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0700
_refine_ls_R_factor_gt           0.0489
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0593P)²+0.8550P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1227
_refine_ls_wR_factor_ref         0.1359
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C17(H17A,H17B), C19(H19A,H19B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C14(H14A,H14B,H14C),
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C18(H18A,H18B,H18C), C20(H20A,H20B,
 H20C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.25480(4) 0.68840(4) 0.50500(3) 0.04067(16) Uani 1 1 d . . . . .
O1 O 0.28472(9) 0.91235(9) 0.54609(8) 0.0371(3) Uani 1 1 d . . . . .
O2 O 0.32812(15) 0.97357(13) 0.27272(11) 0.0712(5) Uani 1 1 d . . . . .
H2 H 0.306123 0.940118 0.219624 0.107 Uiso 1 1 calc GR . . . .
O3 O 0.26719(13) 0.66222(12) 0.60989(10) 0.0616(4) Uani 1 1 d . . . . .
O4 O 0.21431(11) 0.58970(10) 0.43011(10) 0.0533(4) Uani 1 1 d . . . . .
O5 O 0.35332(10) 0.71450(11) 0.48584(9) 0.0461(3) Uani 1 1 d . . . . .
N1 N 0.19637(11) 0.90962(11) 0.45898(11) 0.0386(4) Uani 1 1 d . . . . .
N2 N 0.27105(12) 1.17231(13) 0.65428(13) 0.0477(4) Uani 1 1 d . . . . .
C1 C 0.27296(15) 0.97615(15) 0.62857(13) 0.0426(4) Uani 1 1 d . . . . .
H1 H 0.203294 0.988161 0.616914 0.051 Uiso 1 1 calc R . . . .
C2 C 0.32372(14) 1.08717(15) 0.64051(13) 0.0407(4) Uani 1 1 d . . . . .
C3 C 0.41932(15) 1.09867(18) 0.64318(16) 0.0549(5) Uani 1 1 d . . . . .
H3 H 0.454847 1.037547 0.634753 0.066 Uiso 1 1 calc R . . . .
C4 C 0.46121(17) 1.2021(2) 0.65851(18) 0.0643(6) Uani 1 1 d . . . . .
H4 H 0.525317 1.211784 0.659922 0.077 Uiso 1 1 calc R . . . .
C5 C 0.40749(18) 1.29045(19) 0.67166(17) 0.0617(6) Uani 1 1 d . . . . .
H5 H 0.433916 1.361240 0.681588 0.074 Uiso 1 1 calc R . . . .
C6 C 0.31401(18) 1.27158(17) 0.66975(17) 0.0579(6) Uani 1 1 d . . . . .
H6 H 0.277971 1.331447 0.679835 0.070 Uiso 1 1 calc R . . . .
C7 C 0.3146(2) 0.90835(19) 0.72315(16) 0.0703(7) Uani 1 1 d . . . . .
H7A H 0.282080 0.838112 0.715079 0.105 Uiso 1 1 calc GR . . . .
H7B H 0.304912 0.946991 0.778691 0.105 Uiso 1 1 calc GR . . . .
H7C H 0.383016 0.896993 0.735593 0.105 Uiso 1 1 calc GR . . . .
C8 C 0.21849(15) 0.96534(14) 0.37282(13) 0.0450(5) Uani 1 1 d . . . . .
C9 C 0.1287(2) 0.9604(2) 0.27948(17) 0.0778(8) Uani 1 1 d . . . . .
H9A H 0.112560 0.884659 0.261398 0.117 Uiso 1 1 calc GR . . . .
H9B H 0.142098 0.997888 0.225320 0.117 Uiso 1 1 calc GR . . . .
H9C H 0.074869 0.995716 0.292996 0.117 Uiso 1 1 calc GR . . . .
C10 C 0.2379(2) 1.08703(16) 0.40069(18) 0.0712(8) Uani 1 1 d . . . . .
H10A H 0.188593 1.114454 0.426620 0.107 Uiso 1 1 calc GR . . . .
H10B H 0.236552 1.128627 0.342282 0.107 Uiso 1 1 calc GR . . . .
H10C H 0.300717 1.094560 0.450702 0.107 Uiso 1 1 calc GR . . . .
C11 C 0.30488(17) 0.91498(16) 0.34984(14) 0.0507(5) Uani 1 1 d . . . . .
H11A H 0.361081 0.915354 0.410137 0.061 Uiso 1 1 calc R . . . .
H11B H 0.290212 0.838679 0.329363 0.061 Uiso 1 1 calc R . . . .
C12 C 0.16269(14) 0.79284(14) 0.44441(15) 0.0418(4) Uani 1 1 d . . . . .
H12 H 0.146124 0.779085 0.372369 0.050 Uiso 1 1 calc R . . . .
C13 C 0.06425(16) 0.77626(19) 0.4686(2) 0.0666(7) Uani 1 1 d . . . . .
C14 C 0.0738(2) 0.8033(2) 0.5771(3) 0.0872(9) Uani 1 1 d . . . . .
H14A H 0.126527 0.761452 0.621228 0.131 Uiso 1 1 calc GR . . . .
H14B H 0.014212 0.784495 0.589378 0.131 Uiso 1 1 calc GR . . . .
H14C H 0.086492 0.880788 0.588924 0.131 Uiso 1 1 calc GR . . . .
C15 C 0.0276(2) 0.6565(3) 0.4475(3) 0.1096(12) Uani 1 1 d . . . . .
H15A H 0.026272 0.635652 0.381334 0.164 Uiso 1 1 calc GR . . . .
H15B H -0.036813 0.651017 0.452256 0.164 Uiso 1 1 calc GR . . . .
H15C H 0.070656 0.607960 0.495648 0.164 Uiso 1 1 calc GR . . . .
C16 C -0.0121(2) 0.8531(3) 0.4003(3) 0.1161(13) Uani 1 1 d . . . . .
H16A H 0.010179 0.928224 0.411790 0.174 Uiso 1 1 calc GR . . . .
H16B H -0.072315 0.845641 0.414542 0.174 Uiso 1 1 calc GR . . . .
H16C H -0.022236 0.833907 0.331657 0.174 Uiso 1 1 calc GR . . . .
C17 C 0.2442(2) 0.47792(18) 0.4596(2) 0.0850(9) Uani 1 1 d . . . . .
H17A H 0.239286 0.463556 0.525474 0.102 Uiso 1 1 calc R . . . .
H17B H 0.311638 0.467885 0.463069 0.102 Uiso 1 1 calc R . . . .
C18 C 0.1823(3) 0.4004(2) 0.3871(3) 0.1095(12) Uani 1 1 d . . . . .
H18A H 0.115479 0.411412 0.382981 0.164 Uiso 1 1 calc GR . . . .
H18B H 0.201358 0.325992 0.408264 0.164 Uiso 1 1 calc GR . . . .
H18C H 0.189361 0.412804 0.322578 0.164 Uiso 1 1 calc GR . . . .
C19 C 0.44302(16) 0.7395(2) 0.56508(18) 0.0648(6) Uani 1 1 d . . . . .
H19A H 0.429612 0.749382 0.627657 0.078 Uiso 1 1 calc R . . . .
H19B H 0.470212 0.807949 0.549832 0.078 Uiso 1 1 calc R . . . .
C20 C 0.5139(2) 0.6494(3) 0.5758(2) 0.0916(10) Uani 1 1 d . . . . .
H20A H 0.489130 0.583091 0.596246 0.137 Uiso 1 1 calc GR . . . .
H20B H 0.574475 0.669266 0.625281 0.137 Uiso 1 1 calc GR . . . .
H20C H 0.524345 0.636961 0.512738 0.137 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 O3 1.4661(14) . ?
P1 O4 1.5768(14) . ?
P1 O5 1.5679(15) . ?
P1 C12 1.8368(18) . ?
O1 N1 1.4621(19) . ?
O1 C1 1.451(2) . ?
O2 H2 0.8200 . ?
O2 C11 1.426(2) . ?
O4 C17 1.440(2) . ?
O5 C19 1.448(2) . ?
N1 C8 1.511(2) . ?
N1 C12 1.487(2) . ?
N2 C2 1.333(2) . ?
N2 C6 1.338(3) . ?
C1 H1 0.9800 . ?
C1 C2 1.514(3) . ?
C1 C7 1.516(3) . ?
C2 C3 1.381(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.376(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.370(3) . ?
C5 H5 0.9300 . ?
C5 C6 1.365(3) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C9 1.526(3) . ?
C8 C10 1.526(3) . ?
C8 C11 1.518(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12 0.9800 . ?
C12 C13 1.582(3) . ?
C13 C14 1.526(4) . ?
C13 C15 1.539(4) . ?
C13 C16 1.527(4) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C18 1.463(4) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.472(3) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 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 114.25(8) . . ?
O3 P1 O5 113.22(9) . . ?
O3 P1 C12 116.93(9) . . ?
O4 P1 C12 98.68(8) . . ?
O5 P1 O4 101.56(8) . . ?
O5 P1 C12 110.30(8) . . ?
C1 O1 N1 112.88(13) . . ?
C11 O2 H2 109.5 . . ?
C17 O4 P1 120.33(15) . . ?
C19 O5 P1 123.39(14) . . ?
O1 N1 C8 108.11(13) . . ?
O1 N1 C12 107.29(12) . . ?
C12 N1 C8 117.23(14) . . ?
C2 N2 C6 117.33(18) . . ?
O1 C1 H1 108.9 . . ?
O1 C1 C2 112.52(15) . . ?
O1 C1 C7 107.56(15) . . ?
C2 C1 H1 108.9 . . ?
C2 C1 C7 109.90(17) . . ?
C7 C1 H1 108.9 . . ?
N2 C2 C1 114.91(17) . . ?
N2 C2 C3 122.33(18) . . ?
C3 C2 C1 122.65(17) . . ?
C2 C3 H3 120.5 . . ?
C4 C3 C2 118.93(19) . . ?
C4 C3 H3 120.5 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.3(2) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 H5 121.0 . . ?
C6 C5 C4 118.0(2) . . ?
C6 C5 H5 121.0 . . ?
N2 C6 C5 124.1(2) . . ?
N2 C6 H6 118.0 . . ?
C5 C6 H6 118.0 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N1 C8 C9 109.50(19) . . ?
N1 C8 C10 106.99(15) . . ?
N1 C8 C11 113.28(14) . . ?
C9 C8 C10 107.15(18) . . ?
C11 C8 C9 109.48(18) . . ?
C11 C8 C10 110.23(19) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O2 C11 C8 112.12(17) . . ?
O2 C11 H11A 109.2 . . ?
O2 C11 H11B 109.2 . . ?
C8 C11 H11A 109.2 . . ?
C8 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
P1 C12 H12 105.3 . . ?
N1 C12 P1 115.60(12) . . ?
N1 C12 H12 105.3 . . ?
N1 C12 C13 111.66(15) . . ?
C13 C12 P1 112.51(14) . . ?
C13 C12 H12 105.3 . . ?
C14 C13 C12 113.08(19) . . ?
C14 C13 C15 108.1(2) . . ?
C14 C13 C16 108.4(3) . . ?
C15 C13 C12 110.8(2) . . ?
C16 C13 C12 107.9(2) . . ?
C16 C13 C15 108.4(3) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O4 C17 H17A 109.7 . . ?
O4 C17 H17B 109.7 . . ?
O4 C17 C18 109.9(2) . . ?
H17A C17 H17B 108.2 . . ?
C18 C17 H17A 109.7 . . ?
C18 C17 H17B 109.7 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O5 C19 H19A 109.6 . . ?
O5 C19 H19B 109.6 . . ?
O5 C19 C20 110.4(2) . . ?
H19A C19 H19B 108.1 . . ?
C20 C19 H19A 109.6 . . ?
C20 C19 H19B 109.6 . . ?
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 . . ?

_shelx_SHELXL_version_number     2016/4
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.420
_oxdiff_exptl_absorpt_empirical_full_min 0.642
