# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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_pyethsg1nh2_b
_database_code_depnum_ccdc_archive 'CCDC 1880849'
loop_
_audit_author_name
_audit_author_address
'sylvain MARQUE'
;university Aix MArseille
France
;
_audit_update_record             
;
2018-11-22 deposited with the CCDC.	2019-09-11 downloaded from the CCDC.
;
_audit_creation_date             
;
'Thu Jul 03 17:58:51 2014'
;
_audit_creation_method           
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H38 N3 O4 P, H2 O'
_chemical_formula_sum            'C20 H40 N3 O5 P'
_chemical_formula_weight         433.52
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_symmetry_space_group_name_H-M_alt 'P -1'
_cell_length_a                   9.2786(6)
_cell_length_b                   9.5213(6)
_cell_length_c                   15.4265(6)
_cell_angle_alpha                75.673(4)
_cell_angle_beta                 76.438(4)
_cell_angle_gamma                71.300(5)
_cell_volume                     1232.76(11)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3506
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      72.7970
_cell_measurement_theta_min      4.9730
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.256
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.95862
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             472
_exptl_crystal_size_max          .22
_exptl_crystal_size_mid          .14
_exptl_crystal_size_min          .03
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0197
_diffrn_reflns_av_unetI/netI     0.0383
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            7179
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.946
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.728
_diffrn_reflns_theta_min         4.992
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -49.00   29.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0146   38.0000    0.0000 78

#__ type_ start__ end____ width___ exp.time_
  2 omega  -46.00   35.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0146   38.0000 -150.0000 81

#__ type_ start__ end____ width___ exp.time_
  3 omega  -96.00  -13.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0146  125.0000 -180.0000 83

#__ type_ start__ end____ width___ exp.time_
  4 omega -114.00  -11.00   1.0000    2.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0146  -57.0000   60.0000 103

#__ type_ start__ end____ width___ exp.time_
  5 omega   43.00   90.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -30.0000  -30.0000 47

#__ type_ start__ end____ width___ exp.time_
  6 omega   78.00  178.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719   30.0000   30.0000 100

#__ type_ start__ end____ width___ exp.time_
  7 omega   78.00  174.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719   30.0000  120.0000 96

#__ type_ start__ end____ width___ exp.time_
  8 omega   61.00  121.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719 -125.0000  -60.0000 60

#__ type_ start__ end____ width___ exp.time_
  9 omega   36.00   93.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -45.0000   90.0000 57

#__ type_ start__ end____ width___ exp.time_
 10 omega   42.00  109.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -94.0000  120.0000 67

#__ type_ start__ end____ width___ exp.time_
 11 omega   33.00   92.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -45.0000  150.0000 59

#__ type_ start__ end____ width___ exp.time_
 12 omega   31.00  130.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -77.0000  -30.0000 99

#__ type_ start__ end____ width___ exp.time_
 13 omega   31.00   91.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -30.0000 -150.0000 60
;
_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      -0.1112558000
_diffrn_orient_matrix_UB_12      -0.0998790000
_diffrn_orient_matrix_UB_13      0.0282288000
_diffrn_orient_matrix_UB_21      0.1349476000
_diffrn_orient_matrix_UB_22      -0.1396812000
_diffrn_orient_matrix_UB_23      0.0233858000
_diffrn_orient_matrix_UB_31      -0.0322591000
_diffrn_orient_matrix_UB_32      0.0274009000
_diffrn_orient_matrix_UB_33      0.0979402000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4032
_reflns_number_total             4718
_reflns_odcompleteness_completeness 98.48
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.405
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         4718
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0522
_refine_ls_restrained_S_all      1.053
_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)+(0.0792P)²+0.2551P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1447
_refine_ls_wR_factor_ref         0.1561
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, {H3A,H3B} of O5, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, {H5A,H5B} of O5
2.a Free rotating group:
 O5(H3A,H3B,H5A,H5B)
2.b Ternary CH refined with riding coordinates:
 C1(H1), C12(H12)
2.c Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C17(H17A,H17B), C19(H19A,H19B)
2.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6)
2.e 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)
;
_atom_sites_solution_hydrogens   mixed
_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 0.12961(6) 0.00112(6) 0.71651(4) 0.05558(17) Uani 1 1 d . . . . .
O1 O 0.23083(16) 0.22205(14) 0.75275(8) 0.0512(3) Uani 1 1 d . . . . .
O2 O 0.06022(19) -0.0424(2) 0.81087(12) 0.0797(5) Uani 1 1 d . . . . .
O3 O 0.13965(18) -0.1067(2) 0.65023(13) 0.0717(4) Uani 1 1 d . . . . .
O4 O 0.03359(18) 0.15588(18) 0.66589(11) 0.0653(4) Uani 1 1 d . . . . .
N1 N 0.36975(18) 0.13010(16) 0.70465(10) 0.0469(3) Uani 1 1 d . . . . .
N2 N -0.1891(3) 0.5322(3) 0.93610(16) 0.0881(7) Uani 1 1 d . . . . .
N3 N 0.3870(2) 0.2007(2) 0.96072(13) 0.0665(5) Uani 1 1 d . . . . .
C1 C 0.2377(2) 0.2101(2) 0.84745(12) 0.0504(4) Uani 1 1 d . . . . .
H1 H 0.2330 0.1088 0.8799 0.060 Uiso 1 1 calc R . . . .
C2 C 0.0891(2) 0.3231(2) 0.87980(12) 0.0522(4) Uani 1 1 d . . . . .
C3 C 0.0691(3) 0.4769(2) 0.85486(16) 0.0691(6) Uani 1 1 d . . . . .
H3 H 0.1485 0.5144 0.8180 0.083 Uiso 1 1 calc R . . . .
C4 C -0.0701(4) 0.5748(3) 0.88523(18) 0.0795(7) Uani 1 1 d . . . . .
H4 H -0.0799 0.6778 0.8684 0.095 Uiso 1 1 calc R . . . .
C5 C -0.1699(4) 0.3857(4) 0.9586(2) 0.0990(10) Uani 1 1 d . . . . .
H5 H -0.2530 0.3520 0.9934 0.119 Uiso 1 1 calc R . . . .
C6 C -0.0341(3) 0.2780(3) 0.93399(18) 0.0769(7) Uani 1 1 d . . . . .
H6 H -0.0268 0.1758 0.9541 0.092 Uiso 1 1 calc R . . . .
C7 C 0.3811(3) 0.2368(2) 0.86314(14) 0.0588(5) Uani 1 1 d . . . . .
H7A H 0.4722 0.1739 0.8313 0.071 Uiso 1 1 calc R . . . .
H7B H 0.3798 0.3415 0.8395 0.071 Uiso 1 1 calc R . . . .
C8 C 0.4112(3) 0.2311(2) 0.61630(13) 0.0581(5) Uani 1 1 d . . . . .
C9 C 0.5660(3) 0.1480(3) 0.56690(16) 0.0727(6) Uani 1 1 d . . . . .
H9A H 0.6417 0.1161 0.6060 0.109 Uiso 1 1 calc GR . . . .
H9B H 0.5982 0.2142 0.5131 0.109 Uiso 1 1 calc GR . . . .
H9C H 0.5554 0.0613 0.5505 0.109 Uiso 1 1 calc GR . . . .
C10 C 0.2931(3) 0.2831(3) 0.55284(17) 0.0804(7) Uani 1 1 d . . . . .
H10A H 0.2815 0.1968 0.5365 0.121 Uiso 1 1 calc GR . . . .
H10B H 0.3277 0.3480 0.4991 0.121 Uiso 1 1 calc GR . . . .
H10C H 0.1956 0.3372 0.5829 0.121 Uiso 1 1 calc GR . . . .
C11 C 0.4342(4) 0.3696(3) 0.63889(18) 0.0865(8) Uani 1 1 d . . . . .
H11A H 0.3367 0.4300 0.6651 0.130 Uiso 1 1 calc GR . . . .
H11B H 0.4757 0.4284 0.5844 0.130 Uiso 1 1 calc GR . . . .
H11C H 0.5045 0.3374 0.6814 0.130 Uiso 1 1 calc GR . . . .
C12 C 0.3366(2) -0.0083(2) 0.69600(12) 0.0457(4) Uani 1 1 d . . . . .
H12 H 0.3738 -0.0175 0.6322 0.055 Uiso 1 1 calc R . . . .
C13 C 0.4357(2) -0.1559(2) 0.75211(14) 0.0530(4) Uani 1 1 d . . . . .
C14 C 0.6065(3) -0.1687(3) 0.71749(19) 0.0729(6) Uani 1 1 d . . . . .
H14A H 0.6304 -0.1749 0.6543 0.109 Uiso 1 1 calc GR . . . .
H14B H 0.6675 -0.2579 0.7511 0.109 Uiso 1 1 calc GR . . . .
H14C H 0.6293 -0.0815 0.7252 0.109 Uiso 1 1 calc GR . . . .
C15 C 0.4055(3) -0.2968(3) 0.7375(2) 0.0792(7) Uani 1 1 d . . . . .
H15A H 0.3016 -0.2981 0.7649 0.119 Uiso 1 1 calc GR . . . .
H15B H 0.4764 -0.3855 0.7650 0.119 Uiso 1 1 calc GR . . . .
H15C H 0.4197 -0.2952 0.6737 0.119 Uiso 1 1 calc GR . . . .
C16 C 0.4073(3) -0.1561(3) 0.85366(16) 0.0713(6) Uani 1 1 d . . . . .
H16A H 0.4346 -0.0728 0.8633 0.107 Uiso 1 1 calc GR . . . .
H16B H 0.4692 -0.2490 0.8836 0.107 Uiso 1 1 calc GR . . . .
H16C H 0.3002 -0.1469 0.8780 0.107 Uiso 1 1 calc GR . . . .
C17 C 0.0025(3) -0.1422(4) 0.6456(3) 0.0957(9) Uani 1 1 d . . . . .
H17A H -0.0405 -0.1872 0.7057 0.115 Uiso 1 1 calc R . . . .
H17B H -0.0738 -0.0502 0.6251 0.115 Uiso 1 1 calc R . . . .
C18 C 0.0359(5) -0.2445(5) 0.5850(3) 0.1227(14) Uani 1 1 d . . . . .
H18A H 0.0780 -0.1998 0.5255 0.184 Uiso 1 1 calc GR . . . .
H18B H -0.0573 -0.2657 0.5826 0.184 Uiso 1 1 calc GR . . . .
H18C H 0.1094 -0.3366 0.6063 0.184 Uiso 1 1 calc GR . . . .
C19 C -0.0959(4) 0.2566(5) 0.7129(2) 0.1166(15) Uani 1 1 d . . . . .
H19A H -0.1774 0.2074 0.7379 0.140 Uiso 1 1 calc R . . . .
H19B H -0.0640 0.2767 0.7631 0.140 Uiso 1 1 calc R . . . .
C20 C -0.1530(6) 0.3911(5) 0.6574(4) 0.163(2) Uani 1 1 d . . . . .
H20A H -0.0875 0.4552 0.6491 0.244 Uiso 1 1 calc GR . . . .
H20B H -0.2554 0.4397 0.6847 0.244 Uiso 1 1 calc GR . . . .
H20C H -0.1559 0.3723 0.5996 0.244 Uiso 1 1 calc GR . . . .
O5 O 0.7441(3) 0.0265(3) 0.9131(2) 0.1478(13) Uani 1 1 d . . . . .
H3A H 0.4981 0.1753 0.9668 0.177 Uiso 1 1 d G . . . .
H3B H 0.3340 0.2881 0.9781 0.177 Uiso 1 1 d G . . . .
H5A H 0.8336 0.0045 0.8812 0.222 Uiso 1 1 d G . . . .
H5B H 0.7303 -0.0514 0.9513 0.222 Uiso 1 1 d G . . . .


_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 1.4622(18) . ?
P1 O3 1.5876(17) . ?
P1 O4 1.5779(16) . ?
P1 C12 1.8476(18) . ?
O1 N1 1.4587(18) . ?
O1 C1 1.452(2) . ?
O3 C17 1.438(3) . ?
O4 C19 1.444(3) . ?
N1 C8 1.508(2) . ?
N1 C12 1.489(2) . ?
N2 C4 1.312(4) . ?
N2 C5 1.315(4) . ?
N3 C7 1.469(3) . ?
N3 H3A 1.0022 . ?
N3 H3B 0.8905 . ?
C1 H1 0.9800 . ?
C1 C2 1.516(3) . ?
C1 C7 1.515(3) . ?
C2 C3 1.382(3) . ?
C2 C6 1.371(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.384(3) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C5 C6 1.386(4) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.525(3) . ?
C8 C10 1.523(4) . ?
C8 C11 1.532(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 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12 0.9800 . ?
C12 C13 1.585(3) . ?
C13 C14 1.525(3) . ?
C13 C15 1.533(3) . ?
C13 C16 1.526(3) . ?
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 1.428(5) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.375(6) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
O5 H5A 0.8499 . ?
O5 H5B 0.8502 . ?

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 O3 115.59(12) . . ?
O2 P1 O4 113.89(10) . . ?
O2 P1 C12 116.20(10) . . ?
O3 P1 C12 97.91(8) . . ?
O4 P1 O3 100.06(9) . . ?
O4 P1 C12 111.05(9) . . ?
C1 O1 N1 113.14(13) . . ?
C17 O3 P1 119.28(18) . . ?
C19 O4 P1 122.44(18) . . ?
O1 N1 C8 105.68(14) . . ?
O1 N1 C12 108.30(13) . . ?
C12 N1 C8 115.41(14) . . ?
C4 N2 C5 115.7(2) . . ?
C7 N3 H3A 107.0 . . ?
C7 N3 H3B 102.2 . . ?
H3A N3 H3B 110.5 . . ?
O1 C1 H1 108.4 . . ?
O1 C1 C2 103.16(14) . . ?
O1 C1 C7 114.45(16) . . ?
C2 C1 H1 108.4 . . ?
C7 C1 H1 108.4 . . ?
C7 C1 C2 113.61(16) . . ?
C3 C2 C1 122.00(19) . . ?
C6 C2 C1 121.69(18) . . ?
C6 C2 C3 116.3(2) . . ?
C2 C3 H3 120.3 . . ?
C2 C3 C4 119.4(2) . . ?
C4 C3 H3 120.3 . . ?
N2 C4 C3 124.5(2) . . ?
N2 C4 H4 117.8 . . ?
C3 C4 H4 117.8 . . ?
N2 C5 H5 117.8 . . ?
N2 C5 C6 124.4(3) . . ?
C6 C5 H5 117.8 . . ?
C2 C6 C5 119.6(2) . . ?
C2 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
N3 C7 C1 109.82(18) . . ?
N3 C7 H7A 109.7 . . ?
N3 C7 H7B 109.7 . . ?
C1 C7 H7A 109.7 . . ?
C1 C7 H7B 109.7 . . ?
H7A C7 H7B 108.2 . . ?
N1 C8 C9 108.58(18) . . ?
N1 C8 C10 115.07(19) . . ?
N1 C8 C11 107.78(17) . . ?
C9 C8 C11 107.1(2) . . ?
C10 C8 C9 108.80(19) . . ?
C10 C8 C11 109.2(2) . . ?
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 105.4 . . ?
N1 C12 P1 115.03(12) . . ?
N1 C12 H12 105.4 . . ?
N1 C12 C13 111.78(15) . . ?
C13 C12 P1 112.91(13) . . ?
C13 C12 H12 105.4 . . ?
C14 C13 C12 108.93(17) . . ?
C14 C13 C15 107.29(18) . . ?
C14 C13 C16 106.9(2) . . ?
C15 C13 C12 110.46(18) . . ?
C16 C13 C12 113.77(15) . . ?
C16 C13 C15 109.2(2) . . ?
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 . . ?
O3 C17 H17A 109.4 . . ?
O3 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C18 C17 O3 111.0(3) . . ?
C18 C17 H17A 109.4 . . ?
C18 C17 H17B 109.4 . . ?
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 . . ?
O4 C19 H19A 109.1 . . ?
O4 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
C20 C19 O4 112.6(3) . . ?
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 . . ?
H5A O5 H5B 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_pyethsg1nh2_a
_database_code_depnum_ccdc_archive 'CCDC 1880850'
loop_
_audit_author_name
_audit_author_address
'sylvain MARQUE'
;university Aix MArseille
France
;
_audit_update_record             
;
2018-11-22 deposited with the CCDC.	2019-09-11 downloaded from the CCDC.
;
_audit_creation_date             
;
'Fri Jul 04 14:25:42 2014'
;
_audit_creation_method           
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C20 H38 N3 O4 P'
_chemical_formula_sum            'C20 H38 N3 O4 P'
_chemical_formula_weight         415.50
_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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 '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'

_symmetry_space_group_name_H-M_alt 'P 1 21/c 1'
_cell_length_a                   8.8282(6)
_cell_length_b                   22.0666(14)
_cell_length_c                   12.5309(6)
_cell_angle_alpha                90.0
_cell_angle_beta                 96.936(5)
_cell_angle_gamma                90.0
_cell_volume                     2423.3(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3352
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      73.6920
_cell_measurement_theta_min      4.0570
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.228
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83144
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.139
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             904
_exptl_crystal_size_max          .22
_exptl_crystal_size_mid          .1
_exptl_crystal_size_min          .06
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8051
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.810
_diffrn_reflns_theta_min         4.007
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.3048
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -90.00   -2.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0146  125.0000 -180.0000 88

#__ type_ start__ end____ width___ exp.time_
  2 omega -114.00  -10.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      -40.0146  -57.0000  -60.0000 104

#__ type_ start__ end____ width___ exp.time_
  3 omega  146.00  175.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  125.0000  -30.0000 29

#__ type_ start__ end____ width___ exp.time_
  4 omega   51.00  120.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719 -125.0000  120.0000 69

#__ type_ start__ end____ width___ exp.time_
  5 omega   92.00  178.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719   77.0000  -30.0000 86

#__ type_ start__ end____ width___ exp.time_
  6 omega   41.00   82.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  -45.0000 -180.0000 41

#__ type_ start__ end____ width___ exp.time_
  7 omega   77.00  158.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719   30.0000  -60.0000 81

#__ type_ start__ end____ width___ exp.time_
  8 omega  100.00  177.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      107.6719  125.0000  150.0000 77
;
_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      0.1614556000
_diffrn_orient_matrix_UB_12      -0.0038335000
_diffrn_orient_matrix_UB_13      0.0618903000
_diffrn_orient_matrix_UB_21      -0.0108387000
_diffrn_orient_matrix_UB_22      -0.0697076000
_diffrn_orient_matrix_UB_23      -0.0004366000
_diffrn_orient_matrix_UB_31      0.0684675000
_diffrn_orient_matrix_UB_32      -0.0016842000
_diffrn_orient_matrix_UB_33      -0.1073204000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3780
_reflns_number_total             4694
_reflns_odcompleteness_completeness 98.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    ?
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         4694
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0584
_refine_ls_R_factor_gt           0.0477
_refine_ls_restrained_S_all      1.040
_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)+(0.0726P)²+0.3005P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1301
_refine_ls_wR_factor_ref         0.1430
_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
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)
;
_atom_sites_solution_hydrogens   mixed
_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 0.39878(5) 0.63710(2) 0.04535(4) 0.05667(16) Uani 1 1 d . . . . .
O1 O 0.49711(12) 0.64159(6) 0.26661(9) 0.0515(3) Uani 1 1 d . . . . .
O2 O 0.47515(19) 0.69276(7) 0.01746(12) 0.0713(4) Uani 1 1 d . . . . .
O3 O 0.51148(16) 0.58232(6) 0.06989(11) 0.0629(3) Uani 1 1 d . . . . .
O4 O 0.28253(19) 0.60886(8) -0.04705(12) 0.0775(4) Uani 1 1 d . . . . .
N1 N 0.33305(16) 0.63225(8) 0.26154(12) 0.0556(4) Uani 1 1 d . . . . .
N2 N 0.8694(3) 0.60045(13) 0.59625(18) 0.0933(7) Uani 1 1 d . . . . .
N3 N 0.7146(2) 0.78035(10) 0.36025(16) 0.0728(5) Uani 1 1 d . . . . .
C1 C 0.55750(18) 0.68450(8) 0.34805(12) 0.0502(4) Uani 1 1 d . . . . .
H1 H 0.4734 0.7037 0.3799 0.060 Uiso 1 1 calc R . . . .
C2 C 0.6642(2) 0.65393(9) 0.43496(14) 0.0546(4) Uani 1 1 d . . . . .
C3 C 0.6703(3) 0.67108(11) 0.54136(16) 0.0693(5) Uani 1 1 d . . . . .
H3 H 0.6053 0.7011 0.5614 0.083 Uiso 1 1 calc R . . . .
C4 C 0.7735(3) 0.64346(13) 0.61800(19) 0.0849(7) Uani 1 1 d . . . . .
H4 H 0.7756 0.6559 0.6891 0.102 Uiso 1 1 calc R . . . .
C5 C 0.8641(3) 0.58453(14) 0.4932(2) 0.0894(8) Uani 1 1 d . . . . .
H5 H 0.9309 0.5546 0.4756 0.107 Uiso 1 1 calc R . . . .
C6 C 0.7658(3) 0.60968(12) 0.41090(18) 0.0721(6) Uani 1 1 d . . . . .
H6 H 0.7678 0.5970 0.3403 0.087 Uiso 1 1 calc R . . . .
C7 C 0.6448(2) 0.73249(9) 0.29196(14) 0.0567(4) Uani 1 1 d . . . . .
H7A H 0.7241 0.7123 0.2580 0.068 Uiso 1 1 calc R . . . .
H7B H 0.5750 0.7509 0.2354 0.068 Uiso 1 1 calc R . . . .
C8 C 0.3046(2) 0.57038(10) 0.30805(17) 0.0666(5) Uani 1 1 d . . . . .
C9 C 0.1388(3) 0.55185(17) 0.2804(3) 0.1086(11) Uani 1 1 d . . . . .
H9A H 0.0737 0.5844 0.2977 0.163 Uiso 1 1 calc GR . . . .
H9B H 0.1186 0.5165 0.3210 0.163 Uiso 1 1 calc GR . . . .
H9C H 0.1192 0.5430 0.2049 0.163 Uiso 1 1 calc GR . . . .
C10 C 0.4037(4) 0.52008(13) 0.2714(3) 0.1025(9) Uani 1 1 d . . . . .
H10A H 0.3824 0.5153 0.1949 0.154 Uiso 1 1 calc GR . . . .
H10B H 0.3819 0.4829 0.3062 0.154 Uiso 1 1 calc GR . . . .
H10C H 0.5093 0.5303 0.2898 0.154 Uiso 1 1 calc GR . . . .
C11 C 0.3359(4) 0.57690(16) 0.4294(2) 0.1022(10) Uani 1 1 d . . . . .
H11A H 0.4432 0.5827 0.4498 0.153 Uiso 1 1 calc GR . . . .
H11B H 0.3030 0.5409 0.4631 0.153 Uiso 1 1 calc GR . . . .
H11C H 0.2811 0.6112 0.4520 0.153 Uiso 1 1 calc GR . . . .
C12 C 0.2672(2) 0.64394(9) 0.14885(16) 0.0589(4) Uani 1 1 d . . . . .
H12 H 0.1917 0.6117 0.1319 0.071 Uiso 1 1 calc R . . . .
C13 C 0.1725(2) 0.70457(11) 0.1384(2) 0.0740(6) Uani 1 1 d . . . . .
C14 C 0.0445(3) 0.69876(17) 0.2108(3) 0.1110(11) Uani 1 1 d . . . . .
H14A H -0.0243 0.6671 0.1840 0.166 Uiso 1 1 calc GR . . . .
H14B H -0.0101 0.7364 0.2108 0.166 Uiso 1 1 calc GR . . . .
H14C H 0.0880 0.6892 0.2828 0.166 Uiso 1 1 calc GR . . . .
C15 C 0.2670(3) 0.75983(11) 0.1752(2) 0.0819(6) Uani 1 1 d . . . . .
H15A H 0.3064 0.7553 0.2496 0.123 Uiso 1 1 calc GR . . . .
H15B H 0.2041 0.7954 0.1664 0.123 Uiso 1 1 calc GR . . . .
H15C H 0.3502 0.7637 0.1329 0.123 Uiso 1 1 calc GR . . . .
C16 C 0.0996(3) 0.71480(15) 0.0221(3) 0.1029(9) Uani 1 1 d . . . . .
H16A H 0.1783 0.7212 -0.0233 0.154 Uiso 1 1 calc GR . . . .
H16B H 0.0345 0.7498 0.0193 0.154 Uiso 1 1 calc GR . . . .
H16C H 0.0405 0.6799 -0.0023 0.154 Uiso 1 1 calc GR . . . .
C17 C 0.6742(2) 0.59021(12) 0.09417(18) 0.0742(6) Uani 1 1 d . . . . .
H17A H 0.7095 0.5699 0.1613 0.089 Uiso 1 1 calc R . . . .
H17B H 0.6976 0.6330 0.1028 0.089 Uiso 1 1 calc R . . . .
C18 C 0.7548(3) 0.56488(14) 0.0066(2) 0.0874(7) Uani 1 1 d . . . . .
H18A H 0.7241 0.5865 -0.0589 0.131 Uiso 1 1 calc GR . . . .
H18B H 0.7293 0.5228 -0.0034 0.131 Uiso 1 1 calc GR . . . .
H18C H 0.8630 0.5689 0.0254 0.131 Uiso 1 1 calc GR . . . .
C19 C 0.3322(4) 0.59593(16) -0.1514(2) 0.1004(9) Uani 1 1 d . . . . .
H19A H 0.4122 0.5655 -0.1440 0.120 Uiso 1 1 calc R . . . .
H19B H 0.3722 0.6324 -0.1810 0.120 Uiso 1 1 calc R . . . .
C20 C 0.1986(5) 0.57345(18) -0.2238(3) 0.1274(14) Uani 1 1 d . . . . .
H20A H 0.1626 0.5364 -0.1955 0.191 Uiso 1 1 calc GR . . . .
H20B H 0.2280 0.5662 -0.2940 0.191 Uiso 1 1 calc GR . . . .
H20C H 0.1188 0.6032 -0.2286 0.191 Uiso 1 1 calc GR . . . .
H3A H 0.650(5) 0.797(2) 0.406(3) 0.153 Uiso 1 1 d R . . . .
H3B H 0.786(5) 0.771(2) 0.399(3) 0.153 Uiso 1 1 d 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 O2 1.4636(15) . ?
P1 O3 1.5722(15) . ?
P1 O4 1.5797(14) . ?
P1 C12 1.849(2) . ?
O1 N1 1.4567(17) . ?
O1 C1 1.446(2) . ?
O3 C17 1.443(3) . ?
O4 C19 1.457(3) . ?
N1 C8 1.517(3) . ?
N1 C12 1.483(2) . ?
N2 C4 1.322(4) . ?
N2 C5 1.334(4) . ?
N3 C7 1.449(3) . ?
N3 H3A 0.93(5) . ?
N3 H3B 0.78(4) . ?
C1 H1 0.9800 . ?
C1 C2 1.510(2) . ?
C1 C7 1.530(3) . ?
C2 C3 1.381(3) . ?
C2 C6 1.383(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.383(3) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C5 C6 1.382(3) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.519(3) . ?
C8 C10 1.518(4) . ?
C8 C11 1.519(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 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12 0.9800 . ?
C12 C13 1.575(3) . ?
C13 C14 1.538(4) . ?
C13 C15 1.517(3) . ?
C13 C16 1.537(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 1.487(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C20 1.483(4) . ?
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
O2 P1 O3 113.14(9) . . ?
O2 P1 O4 115.68(9) . . ?
O2 P1 C12 116.46(9) . . ?
O3 P1 O4 100.36(8) . . ?
O3 P1 C12 111.21(8) . . ?
O4 P1 C12 97.98(9) . . ?
C1 O1 N1 113.79(12) . . ?
C17 O3 P1 122.61(15) . . ?
C19 O4 P1 119.73(18) . . ?
O1 N1 C8 108.69(14) . . ?
O1 N1 C12 106.86(13) . . ?
C12 N1 C8 117.26(15) . . ?
C4 N2 C5 116.1(2) . . ?
C7 N3 H3A 113(3) . . ?
C7 N3 H3B 115(4) . . ?
H3A N3 H3B 104(4) . . ?
O1 C1 H1 109.7 . . ?
O1 C1 C2 111.17(15) . . ?
O1 C1 C7 106.99(13) . . ?
C2 C1 H1 109.7 . . ?
C2 C1 C7 109.62(14) . . ?
C7 C1 H1 109.7 . . ?
C3 C2 C1 121.48(18) . . ?
C3 C2 C6 116.95(18) . . ?
C6 C2 C1 121.49(17) . . ?
C2 C3 H3 120.2 . . ?
C2 C3 C4 119.7(2) . . ?
C4 C3 H3 120.2 . . ?
N2 C4 C3 123.9(2) . . ?
N2 C4 H4 118.0 . . ?
C3 C4 H4 118.0 . . ?
N2 C5 H5 117.9 . . ?
N2 C5 C6 124.2(3) . . ?
C6 C5 H5 117.9 . . ?
C2 C6 H6 120.5 . . ?
C5 C6 C2 119.1(2) . . ?
C5 C6 H6 120.5 . . ?
N3 C7 C1 115.79(16) . . ?
N3 C7 H7A 108.3 . . ?
N3 C7 H7B 108.3 . . ?
C1 C7 H7A 108.3 . . ?
C1 C7 H7B 108.3 . . ?
H7A C7 H7B 107.4 . . ?
N1 C8 C9 110.7(2) . . ?
N1 C8 C10 114.42(17) . . ?
N1 C8 C11 106.30(19) . . ?
C10 C8 C9 108.0(3) . . ?
C10 C8 C11 109.3(2) . . ?
C11 C8 C9 107.9(2) . . ?
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 104.9 . . ?
N1 C12 P1 116.53(12) . . ?
N1 C12 H12 104.9 . . ?
N1 C12 C13 111.72(17) . . ?
C13 C12 P1 112.52(15) . . ?
C13 C12 H12 104.9 . . ?
C14 C13 C12 107.5(2) . . ?
C15 C13 C12 113.00(16) . . ?
C15 C13 C14 107.7(2) . . ?
C15 C13 C16 108.8(2) . . ?
C16 C13 C12 111.2(2) . . ?
C16 C13 C14 108.6(2) . . ?
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 . . ?
O3 C17 H17A 109.5 . . ?
O3 C17 H17B 109.5 . . ?
O3 C17 C18 110.60(19) . . ?
H17A C17 H17B 108.1 . . ?
C18 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
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 . . ?
O4 C19 H19A 110.1 . . ?
O4 C19 H19B 110.1 . . ?
O4 C19 C20 108.1(3) . . ?
H19A C19 H19B 108.4 . . ?
C20 C19 H19A 110.1 . . ?
C20 C19 H19B 110.1 . . ?
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'
