# Electronic Supplementary Material (ESI) for RSC Medicinal Chemistry.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_4a-2
_database_code_depnum_ccdc_archive 'CCDC 2203659'
loop_
_audit_author_name
_audit_author_address
'Arto Valkonen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2022-08-26 deposited with the CCDC.	2023-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H36 N3 O6 P S2'
_chemical_formula_sum            'C21 H36 N3 O6 P S2'
_chemical_formula_weight         521.62

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.8864(6)
_cell_length_b                   17.0353(6)
_cell_length_c                   13.0083(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.201(4)
_cell_angle_gamma                90
_cell_volume                     2629.92(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    2121
_cell_measurement_theta_min      2.0890
_cell_measurement_theta_max      29.6860

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.317
_exptl_crystal_F_000             1112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.303
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_T_max  0.989
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0107
_diffrn_reflns_number            11537
_diffrn_reflns_av_unetI/netI     0.0832
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.972
_diffrn_reflns_theta_max         29.890
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.866
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.866
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.866
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6569
_reflns_number_gt                4425
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    SHELXL-2018/3
_computing_publication_material  SHELXL-2018/3
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0361P)²+0.6935P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6569
_refine_ls_number_parameters     305
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0989
_refine_ls_R_factor_gt           0.0597
_refine_ls_wR_factor_ref         0.1199
_refine_ls_wR_factor_gt          0.1056
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S13 S 0.42663(5) 0.54916(4) 0.65221(5) 0.01960(15) Uani 1 1 d . . . . .
S14 S 0.47284(6) 0.38980(4) 0.74804(5) 0.02782(18) Uani 1 1 d . . . . .
P1 P 0.17154(6) 0.68769(4) 0.31072(5) 0.02324(17) Uani 1 1 d . . . . .
O1 O 0.19298(15) 0.60485(10) 0.33828(14) 0.0257(4) Uani 1 1 d . . . . .
O10 O 0.32921(16) 0.69247(11) 0.57872(13) 0.0272(4) Uani 1 1 d . . . . .
O1A O 0.04810(17) 0.71573(11) 0.32422(16) 0.0377(5) Uani 1 1 d . . . . .
O1B O 0.19896(19) 0.70802(10) 0.19758(14) 0.0366(5) Uani 1 1 d . . . . .
O4C O 0.53365(17) 0.91578(11) 0.43166(14) 0.0324(5) Uani 1 1 d . . . . .
O5C O 0.46449(15) 0.86019(10) 0.28202(13) 0.0243(4) Uani 1 1 d . . . . .
N4 N 0.34732(18) 0.88562(12) 0.40740(15) 0.0204(5) Uani 1 1 d . . . . .
N9 N 0.36378(18) 0.72332(12) 0.41448(15) 0.0188(5) Uani 1 1 d D . . . .
H9 H 0.409(2) 0.7156(14) 0.3650(16) 0.023 Uiso 1 1 d D U . . .
N15 N 0.61174(18) 0.48005(12) 0.64012(15) 0.0188(5) Uani 1 1 d D . . . .
H15 H 0.6710(17) 0.4483(13) 0.6499(19) 0.023 Uiso 1 1 d D U . . .
C2 C 0.2523(2) 0.75646(14) 0.39161(18) 0.0177(5) Uani 1 1 d . . . . .
H2 H 0.214640 0.759653 0.458317 0.021 Uiso 1 1 calc R U . . .
C3 C 0.2589(2) 0.84176(14) 0.34923(19) 0.0197(5) Uani 1 1 d . . . . .
H3 H 0.279331 0.838931 0.275777 0.024 Uiso 1 1 calc R U . . .
C5 C 0.3254(2) 0.90674(15) 0.51356(19) 0.0257(6) Uani 1 1 d . . . . .
H5A H 0.387742 0.939771 0.542905 0.031 Uiso 1 1 calc R U . . .
H5B H 0.321975 0.858538 0.555784 0.031 Uiso 1 1 calc R U . . .
C6 C 0.2151(3) 0.95115(16) 0.5172(2) 0.0315(7) Uani 1 1 d . . . . .
H6A H 0.222827 1.003024 0.484033 0.038 Uiso 1 1 calc R U . . .
H6B H 0.198013 0.960071 0.589906 0.038 Uiso 1 1 calc R U . . .
C7 C 0.1184(2) 0.90646(16) 0.4629(2) 0.0312(7) Uani 1 1 d . . . . .
H7A H 0.049283 0.938933 0.461097 0.037 Uiso 1 1 calc R U . . .
H7B H 0.103750 0.857658 0.501266 0.037 Uiso 1 1 calc R U . . .
C8 C 0.1477(2) 0.88615(15) 0.3532(2) 0.0260(6) Uani 1 1 d . . . . .
H8A H 0.086513 0.853718 0.320587 0.031 Uiso 1 1 calc R U . . .
H8B H 0.152395 0.935217 0.312873 0.031 Uiso 1 1 calc R U . . .
C10 C 0.3939(2) 0.69522(14) 0.50894(19) 0.0185(5) Uani 1 1 d . . . . .
C11 C 0.5156(2) 0.67110(14) 0.52723(19) 0.0203(5) Uani 1 1 d . . . . .
H11A H 0.550633 0.667609 0.460085 0.024 Uiso 1 1 calc R U . . .
H11B H 0.556001 0.712286 0.568350 0.024 Uiso 1 1 calc R U . . .
C12 C 0.5303(2) 0.59383(13) 0.58219(18) 0.0163(5) Uani 1 1 d . . . . .
C14 C 0.5119(2) 0.46873(14) 0.68070(18) 0.0198(5) Uani 1 1 d . . . . .
C16 C 0.6233(2) 0.54917(14) 0.58554(18) 0.0182(5) Uani 1 1 d . . . . .
C2A C -0.0458(3) 0.68093(19) 0.2619(2) 0.0389(8) Uani 1 1 d . . . . .
H2A H -0.075136 0.719132 0.209684 0.047 Uiso 1 1 calc R U . . .
H2B H -0.019611 0.633780 0.225660 0.047 Uiso 1 1 calc R U . . .
C3A C -0.1344(3) 0.65947(19) 0.3300(3) 0.0448(8) Uani 1 1 d . . . . .
H3A H -0.197738 0.636104 0.289331 0.067 Uiso 1 1 calc R U . . .
H3B H -0.104774 0.621403 0.381085 0.067 Uiso 1 1 calc R U . . .
H3C H -0.160121 0.706482 0.365161 0.067 Uiso 1 1 calc R U . . .
C2B C 0.2280(3) 0.64895(17) 0.1220(2) 0.0327(7) Uani 1 1 d . . . . .
H2C H 0.158919 0.629201 0.084634 0.039 Uiso 1 1 calc R U . . .
H2D H 0.266797 0.604099 0.157043 0.039 Uiso 1 1 calc R U . . .
C3B C 0.3031(3) 0.68608(19) 0.0490(2) 0.0441(8) Uani 1 1 d . . . . .
H3D H 0.323696 0.647409 -0.002468 0.066 Uiso 1 1 calc R U . . .
H3E H 0.263907 0.730214 0.014492 0.066 Uiso 1 1 calc R U . . .
H3F H 0.371400 0.705201 0.086642 0.066 Uiso 1 1 calc R U . . .
C4C C 0.4557(2) 0.88921(14) 0.3785(2) 0.0232(6) Uani 1 1 d . . . . .
C6C C 0.5707(2) 0.87054(16) 0.2289(2) 0.0258(6) Uani 1 1 d . . . . .
C7C C 0.6667(2) 0.82834(18) 0.2862(2) 0.0363(7) Uani 1 1 d . . . . .
H7C H 0.736037 0.835842 0.249994 0.054 Uiso 1 1 calc R U . . .
H7D H 0.676951 0.849586 0.356090 0.054 Uiso 1 1 calc R U . . .
H7E H 0.649448 0.772177 0.289656 0.054 Uiso 1 1 calc R U . . .
C8C C 0.5431(3) 0.83251(18) 0.1256(2) 0.0370(7) Uani 1 1 d . . . . .
H8C H 0.608654 0.836004 0.083335 0.056 Uiso 1 1 calc R U . . .
H8D H 0.523826 0.777227 0.135759 0.056 Uiso 1 1 calc R U . . .
H8E H 0.479061 0.859637 0.090814 0.056 Uiso 1 1 calc R U . . .
C9C C 0.5929(3) 0.95742(17) 0.2161(2) 0.0388(8) Uani 1 1 d . . . . .
H9A H 0.663005 0.964745 0.181023 0.058 Uiso 1 1 calc R U . . .
H9B H 0.530255 0.981236 0.174962 0.058 Uiso 1 1 calc R U . . .
H9C H 0.599752 0.982524 0.283921 0.058 Uiso 1 1 calc R U . . .
C16D C 0.7337(2) 0.56605(16) 0.5404(2) 0.0272(6) Uani 1 1 d . . . . .
H16A H 0.721736 0.601576 0.481583 0.041 Uiso 1 1 calc R U . . .
H16B H 0.766992 0.516888 0.517512 0.041 Uiso 1 1 calc R U . . .
H16C H 0.784697 0.590771 0.592662 0.041 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S13 C14 1.732(3) . ?
S13 C12 1.748(2) . ?
S14 C14 1.684(3) . ?
P1 O1 1.4748(18) . ?
P1 O1A 1.562(2) . ?
P1 O1B 1.5639(19) . ?
P1 C2 1.813(3) . ?
O10 C10 1.223(3) . ?
O1A C2A 1.467(3) . ?
O1B C2B 1.462(3) . ?
O4C C4C 1.212(3) . ?
O5C C4C 1.358(3) . ?
O5C C6C 1.483(3) . ?
N4 C4C 1.364(3) . ?
N4 C5 1.465(3) . ?
N4 C3 1.465(3) . ?
N9 C10 1.348(3) . ?
N9 C2 1.456(3) . ?
N15 C14 1.340(3) . ?
N15 C16 1.386(3) . ?
C2 C3 1.558(3) . ?
C3 C8 1.526(3) . ?
C5 C6 1.516(4) . ?
C6 C7 1.519(4) . ?
C7 C8 1.528(4) . ?
C10 C11 1.510(3) . ?
C11 C12 1.503(3) . ?
C12 C16 1.340(3) . ?
C16 C16D 1.495(3) . ?
C2A C3A 1.460(4) . ?
C2B C3B 1.481(4) . ?
C6C C7C 1.509(4) . ?
C6C C8C 1.511(4) . ?
C6C C9C 1.514(4) . ?

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
C14 S13 C12 92.00(12) . . ?
O1 P1 O1A 114.58(11) . . ?
O1 P1 O1B 113.48(11) . . ?
O1A P1 O1B 106.53(12) . . ?
O1 P1 C2 113.48(11) . . ?
O1A P1 C2 101.98(11) . . ?
O1B P1 C2 105.76(11) . . ?
C2A O1A P1 120.29(19) . . ?
C2B O1B P1 123.36(17) . . ?
C4C O5C C6C 119.9(2) . . ?
C4C N4 C5 118.0(2) . . ?
C4C N4 C3 122.8(2) . . ?
C5 N4 C3 116.9(2) . . ?
C10 N9 C2 121.1(2) . . ?
C14 N15 C16 116.1(2) . . ?
N9 C2 C3 111.8(2) . . ?
N9 C2 P1 108.33(16) . . ?
C3 C2 P1 115.65(16) . . ?
N4 C3 C8 109.1(2) . . ?
N4 C3 C2 109.99(19) . . ?
C8 C3 C2 112.9(2) . . ?
N4 C5 C6 110.6(2) . . ?
C5 C6 C7 111.6(2) . . ?
C6 C7 C8 110.0(2) . . ?
C3 C8 C7 112.8(2) . . ?
O10 C10 N9 122.9(2) . . ?
O10 C10 C11 120.6(2) . . ?
N9 C10 C11 116.3(2) . . ?
C12 C11 C10 113.5(2) . . ?
C16 C12 C11 125.9(2) . . ?
C16 C12 S13 109.88(18) . . ?
C11 C12 S13 124.22(18) . . ?
N15 C14 S14 126.6(2) . . ?
N15 C14 S13 108.81(18) . . ?
S14 C14 S13 124.63(16) . . ?
C12 C16 N15 113.2(2) . . ?
C12 C16 C16D 128.2(2) . . ?
N15 C16 C16D 118.6(2) . . ?
C3A C2A O1A 108.5(3) . . ?
O1B C2B C3B 108.1(2) . . ?
O4C C4C O5C 124.6(3) . . ?
O4C C4C N4 124.3(2) . . ?
O5C C4C N4 111.1(2) . . ?
O5C C6C C7C 110.7(2) . . ?
O5C C6C C8C 102.4(2) . . ?
C7C C6C C8C 110.8(2) . . ?
O5C C6C C9C 109.0(2) . . ?
C7C C6C C9C 112.9(3) . . ?
C8C C6C C9C 110.6(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
O1 P1 O1A C2A -63.8(2) . . . . ?
O1B P1 O1A C2A 62.5(2) . . . . ?
C2 P1 O1A C2A 173.2(2) . . . . ?
O1 P1 O1B C2B 8.0(3) . . . . ?
O1A P1 O1B C2B -119.0(2) . . . . ?
C2 P1 O1B C2B 133.0(2) . . . . ?
C10 N9 C2 C3 124.1(2) . . . . ?
C10 N9 C2 P1 -107.3(2) . . . . ?
O1 P1 C2 N9 37.7(2) . . . . ?
O1A P1 C2 N9 161.43(16) . . . . ?
O1B P1 C2 N9 -87.35(18) . . . . ?
O1 P1 C2 C3 164.00(17) . . . . ?
O1A P1 C2 C3 -72.2(2) . . . . ?
O1B P1 C2 C3 39.0(2) . . . . ?
C4C N4 C3 C8 -144.1(2) . . . . ?
C5 N4 C3 C8 53.5(3) . . . . ?
C4C N4 C3 C2 91.5(3) . . . . ?
C5 N4 C3 C2 -70.9(3) . . . . ?
N9 C2 C3 N4 -41.6(3) . . . . ?
P1 C2 C3 N4 -166.13(16) . . . . ?
N9 C2 C3 C8 -163.7(2) . . . . ?
P1 C2 C3 C8 71.7(2) . . . . ?
C4C N4 C5 C6 142.2(2) . . . . ?
C3 N4 C5 C6 -54.5(3) . . . . ?
N4 C5 C6 C7 53.2(3) . . . . ?
C5 C6 C7 C8 -54.2(3) . . . . ?
N4 C3 C8 C7 -52.5(3) . . . . ?
C2 C3 C8 C7 70.1(3) . . . . ?
C6 C7 C8 C3 54.6(3) . . . . ?
C2 N9 C10 O10 3.4(4) . . . . ?
C2 N9 C10 C11 -173.1(2) . . . . ?
O10 C10 C11 C12 48.0(3) . . . . ?
N9 C10 C11 C12 -135.4(2) . . . . ?
C10 C11 C12 C16 162.1(2) . . . . ?
C10 C11 C12 S13 -18.1(3) . . . . ?
C14 S13 C12 C16 -1.87(19) . . . . ?
C14 S13 C12 C11 178.3(2) . . . . ?
C16 N15 C14 S14 178.50(18) . . . . ?
C16 N15 C14 S13 -1.2(3) . . . . ?
C12 S13 C14 N15 1.70(18) . . . . ?
C12 S13 C14 S14 -177.98(17) . . . . ?
C11 C12 C16 N15 -178.6(2) . . . . ?
S13 C12 C16 N15 1.5(3) . . . . ?
C11 C12 C16 C16D 2.6(4) . . . . ?
S13 C12 C16 C16D -177.2(2) . . . . ?
C14 N15 C16 C12 -0.3(3) . . . . ?
C14 N15 C16 C16D 178.6(2) . . . . ?
P1 O1A C2A C3A 131.8(2) . . . . ?
P1 O1B C2B C3B -150.7(2) . . . . ?
C6C O5C C4C O4C -9.2(4) . . . . ?
C6C O5C C4C N4 169.9(2) . . . . ?
C5 N4 C4C O4C -7.3(4) . . . . ?
C3 N4 C4C O4C -169.6(2) . . . . ?
C5 N4 C4C O5C 173.53(19) . . . . ?
C3 N4 C4C O5C 11.3(3) . . . . ?
C4C O5C C6C C7C 63.3(3) . . . . ?
C4C O5C C6C C8C -178.5(2) . . . . ?
C4C O5C C6C C9C -61.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N9 H9 S14 0.869(16) 2.757(19) 3.523(2) 148(2) 3_666 yes
N15 H15 O1 0.893(16) 1.851(17) 2.736(3) 171(2) 3_666 yes

_refine_diff_density_max         0.418
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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_4e-2
_database_code_depnum_ccdc_archive 'CCDC 2203663'
loop_
_audit_author_name
_audit_author_address
'Arto Valkonen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2022-08-26 deposited with the CCDC.	2023-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H39 N2 O6 P S'
_chemical_formula_sum            'C24 H39 N2 O6 P S'
_chemical_formula_weight         514.60

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'
S S 0.1246 0.1234 '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'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.9148(6)
_cell_length_b                   10.9400(6)
_cell_length_c                   14.0426(7)
_cell_angle_alpha                83.162(4)
_cell_angle_beta                 71.761(5)
_cell_angle_gamma                64.421(6)
_cell_volume                     1304.63(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4778
_cell_measurement_theta_min      2.4040
_cell_measurement_theta_max      29.6390

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.310
_exptl_crystal_F_000             552
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.600
_exptl_crystal_size_mid          0.390
_exptl_crystal_size_min          0.370
_exptl_absorpt_coefficient_mu    0.226
_shelx_estimated_absorpt_T_min   0.876
_shelx_estimated_absorpt_T_max   0.921
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.911
_exptl_absorpt_correction_T_max  0.938
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0107
_diffrn_reflns_number            11256
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_av_R_equivalents  0.0216
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.064
_diffrn_reflns_theta_max         29.874
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.871
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.871
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.871
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6556
_reflns_number_gt                5416
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    SHELXL-2018/3
_computing_publication_material  SHELXL-2018/3
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0386P)²+0.4220P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6556
_refine_ls_number_parameters     310
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1032
_refine_ls_wR_factor_gt          0.0943
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S13 S 0.20346(5) 1.07917(4) 0.92235(3) 0.02397(11) Uani 1 1 d . . . . .
P1 P 0.46299(5) 0.82186(4) 0.44645(3) 0.01591(10) Uani 1 1 d . . . . .
O1 O 0.53235(14) 0.91808(11) 0.40325(8) 0.0209(2) Uani 1 1 d . . . . .
O10 O 0.35244(14) 0.67357(11) 0.73056(8) 0.0227(3) Uani 1 1 d . . . . .
O1A O 0.27968(13) 0.88488(11) 0.48620(8) 0.0196(2) Uani 1 1 d . . . . .
O1B O 0.49726(14) 0.70865(11) 0.37149(8) 0.0210(2) Uani 1 1 d . . . . .
O4C O 0.77898(15) 0.78996(11) 0.65158(9) 0.0241(3) Uani 1 1 d . . . . .
O5C O 0.80830(15) 0.61520(11) 0.76004(8) 0.0236(3) Uani 1 1 d . . . . .
N4 N 0.75816(16) 0.60138(12) 0.61748(9) 0.0163(3) Uani 1 1 d . . . . .
N9 N 0.45748(15) 0.81275(13) 0.63737(9) 0.0156(3) Uani 1 1 d D . . . .
H9 H 0.483(2) 0.8792(16) 0.6390(13) 0.019 Uiso 1 1 d D U . . .
C2 C 0.53327(18) 0.72434(15) 0.54902(11) 0.0151(3) Uani 1 1 d . . . . .
H2 H 0.498990 0.648751 0.563192 0.018 Uiso 1 1 calc R U . . .
C3 C 0.71413(18) 0.66127(15) 0.52635(11) 0.0165(3) Uani 1 1 d . . . . .
H3 H 0.749513 0.735819 0.505489 0.020 Uiso 1 1 calc R U . . .
C5 C 0.7434(2) 0.47384(15) 0.65134(12) 0.0194(3) Uani 1 1 d . . . . .
H5A H 0.631468 0.491258 0.675145 0.023 Uiso 1 1 calc R U . . .
H5B H 0.787987 0.438504 0.708111 0.023 Uiso 1 1 calc R U . . .
C6 C 0.8285(2) 0.36858(16) 0.56631(12) 0.0222(3) Uani 1 1 d . . . . .
H6A H 0.942552 0.340324 0.550052 0.027 Uiso 1 1 calc R U . . .
H6B H 0.807195 0.287602 0.588281 0.027 Uiso 1 1 calc R U . . .
C7 C 0.7768(2) 0.42438(17) 0.47316(12) 0.0232(3) Uani 1 1 d . . . . .
H7A H 0.665054 0.443992 0.487087 0.028 Uiso 1 1 calc R U . . .
H7B H 0.838380 0.356136 0.417903 0.028 Uiso 1 1 calc R U . . .
C8 C 0.80035(19) 0.55362(16) 0.44202(12) 0.0202(3) Uani 1 1 d . . . . .
H8A H 0.762319 0.591037 0.382925 0.024 Uiso 1 1 calc R U . . .
H8B H 0.913464 0.531520 0.422141 0.024 Uiso 1 1 calc R U . . .
C10 C 0.37565(18) 0.77595(15) 0.72414(11) 0.0160(3) Uani 1 1 d . . . . .
C11 C 0.31300(18) 0.86883(15) 0.81198(11) 0.0166(3) Uani 1 1 d . . . . .
C12 C 0.27775(19) 1.00448(16) 0.80602(11) 0.0198(3) Uani 1 1 d . . . . .
H12 H 0.292692 1.051312 0.744894 0.024 Uiso 1 1 calc R U . . .
C14 C 0.2196(2) 0.92783(16) 0.98155(12) 0.0204(3) Uani 1 1 d . . . . .
C15 C 0.1763(2) 0.91654(18) 1.09400(12) 0.0277(4) Uani 1 1 d . . . . .
H15A H 0.067891 0.983507 1.124000 0.033 Uiso 1 1 calc R U . . .
H15B H 0.246808 0.936784 1.119837 0.033 Uiso 1 1 calc R U . . .
C16 C 0.1897(2) 0.77354(17) 1.12405(12) 0.0261(4) Uani 1 1 d . . . . .
H16A H 0.196892 0.757231 1.193542 0.031 Uiso 1 1 calc R U . . .
H16B H 0.094484 0.766022 1.122427 0.031 Uiso 1 1 calc R U . . .
C17 C 0.3326(2) 0.66644(17) 1.05410(12) 0.0250(4) Uani 1 1 d . . . . .
H17A H 0.343452 0.575150 1.079180 0.030 Uiso 1 1 calc R U . . .
H17B H 0.427563 0.676445 1.053213 0.030 Uiso 1 1 calc R U . . .
C18 C 0.3182(2) 0.68014(16) 0.94761(12) 0.0230(3) Uani 1 1 d . . . . .
H18A H 0.417795 0.618501 0.901323 0.028 Uiso 1 1 calc R U . . .
H18B H 0.234812 0.654166 0.946041 0.028 Uiso 1 1 calc R U . . .
C19 C 0.27961(18) 0.82480(16) 0.91399(11) 0.0180(3) Uani 1 1 d . . . . .
C2A C 0.18768(19) 1.01486(16) 0.54038(12) 0.0209(3) Uani 1 1 d . . . . .
H2A1 H 0.141808 1.086700 0.495207 0.025 Uiso 1 1 calc R U . . .
H2A2 H 0.255101 1.040131 0.565622 0.025 Uiso 1 1 calc R U . . .
C3A C 0.0599(2) 1.00018(18) 0.62669(13) 0.0270(4) Uani 1 1 d . . . . .
H3A1 H -0.003535 1.086284 0.664274 0.040 Uiso 1 1 calc R U . . .
H3A2 H -0.006337 0.975556 0.600911 0.040 Uiso 1 1 calc R U . . .
H3A3 H 0.106536 0.929160 0.671064 0.040 Uiso 1 1 calc R U . . .
C2B C 0.4907(2) 0.7450(2) 0.26882(12) 0.0296(4) Uani 1 1 d . . . . .
H2B1 H 0.477620 0.839948 0.256582 0.035 Uiso 1 1 calc R U . . .
H2B2 H 0.400347 0.737101 0.258656 0.035 Uiso 1 1 calc R U . . .
C3B C 0.6383(3) 0.6521(2) 0.19795(14) 0.0414(5) Uani 1 1 d . . . . .
H3B1 H 0.635099 0.675644 0.128898 0.062 Uiso 1 1 calc R U . . .
H3B2 H 0.727135 0.660986 0.208080 0.062 Uiso 1 1 calc R U . . .
H3B3 H 0.650092 0.558445 0.210148 0.062 Uiso 1 1 calc R U . . .
C4C C 0.78078(18) 0.67884(16) 0.67511(11) 0.0181(3) Uani 1 1 d . . . . .
C6C C 0.8255(2) 0.68642(18) 0.83583(12) 0.0229(3) Uani 1 1 d . . . . .
C7C C 0.6747(2) 0.8110(2) 0.87512(14) 0.0344(4) Uani 1 1 d . . . . .
H7C1 H 0.685934 0.858161 0.925266 0.052 Uiso 1 1 calc R U . . .
H7C2 H 0.651744 0.871751 0.819521 0.052 Uiso 1 1 calc R U . . .
H7C3 H 0.588920 0.783471 0.905957 0.052 Uiso 1 1 calc R U . . .
C8C C 0.8531(3) 0.5812(2) 0.91656(14) 0.0374(5) Uani 1 1 d . . . . .
H8C1 H 0.866353 0.617762 0.971692 0.056 Uiso 1 1 calc R U . . .
H8C2 H 0.763153 0.558003 0.941857 0.056 Uiso 1 1 calc R U . . .
H8C3 H 0.947541 0.499623 0.888320 0.056 Uiso 1 1 calc R U . . .
C9C C 0.9663(2) 0.7191(2) 0.79366(13) 0.0302(4) Uani 1 1 d . . . . .
H9C1 H 0.975086 0.766112 0.845150 0.045 Uiso 1 1 calc R U . . .
H9C2 H 1.061040 0.634942 0.773026 0.045 Uiso 1 1 calc R U . . .
H9C3 H 0.954085 0.777546 0.735526 0.045 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S13 C12 1.7098(16) . ?
S13 C14 1.7276(16) . ?
P1 O1 1.4700(11) . ?
P1 O1A 1.5700(12) . ?
P1 O1B 1.5750(11) . ?
P1 C2 1.8217(15) . ?
O10 C10 1.2252(18) . ?
O1A C2A 1.4615(19) . ?
O1B C2B 1.4633(19) . ?
O4C C4C 1.2151(18) . ?
O5C C4C 1.3504(18) . ?
O5C C6C 1.4813(18) . ?
N4 C4C 1.3654(19) . ?
N4 C3 1.4699(19) . ?
N4 C5 1.4728(19) . ?
N9 C10 1.3607(19) . ?
N9 C2 1.4539(18) . ?
C2 C3 1.555(2) . ?
C3 C8 1.533(2) . ?
C5 C6 1.524(2) . ?
C6 C7 1.519(2) . ?
C7 C8 1.523(2) . ?
C10 C11 1.488(2) . ?
C11 C12 1.368(2) . ?
C11 C19 1.439(2) . ?
C14 C19 1.359(2) . ?
C14 C15 1.506(2) . ?
C15 C16 1.530(2) . ?
C16 C17 1.521(2) . ?
C17 C18 1.530(2) . ?
C18 C19 1.512(2) . ?
C2A C3A 1.506(2) . ?
C2B C3B 1.487(3) . ?
C6C C9C 1.514(2) . ?
C6C C8C 1.516(2) . ?
C6C C7C 1.517(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C12 S13 C14 92.31(8) . . ?
O1 P1 O1A 115.64(7) . . ?
O1 P1 O1B 114.99(7) . . ?
O1A P1 O1B 101.59(6) . . ?
O1 P1 C2 113.84(7) . . ?
O1A P1 C2 106.32(7) . . ?
O1B P1 C2 102.93(6) . . ?
C2A O1A P1 122.72(10) . . ?
C2B O1B P1 119.27(10) . . ?
C4C O5C C6C 119.69(12) . . ?
C4C N4 C3 117.96(12) . . ?
C4C N4 C5 123.48(12) . . ?
C3 N4 C5 117.32(12) . . ?
C10 N9 C2 120.46(13) . . ?
N9 C2 C3 110.84(12) . . ?
N9 C2 P1 107.78(10) . . ?
C3 C2 P1 114.04(10) . . ?
N4 C3 C8 109.20(12) . . ?
N4 C3 C2 110.07(12) . . ?
C8 C3 C2 113.44(12) . . ?
N4 C5 C6 110.71(13) . . ?
C7 C6 C5 111.35(13) . . ?
C6 C7 C8 109.87(13) . . ?
C7 C8 C3 112.31(13) . . ?
O10 C10 N9 122.77(14) . . ?
O10 C10 C11 121.21(14) . . ?
N9 C10 C11 116.02(13) . . ?
C12 C11 C19 112.34(14) . . ?
C12 C11 C10 124.73(14) . . ?
C19 C11 C10 122.92(13) . . ?
C11 C12 S13 111.55(12) . . ?
C19 C14 C15 126.37(14) . . ?
C19 C14 S13 111.29(12) . . ?
C15 C14 S13 122.31(12) . . ?
C14 C15 C16 110.15(14) . . ?
C17 C16 C15 111.50(14) . . ?
C16 C17 C18 110.81(14) . . ?
C19 C18 C17 109.85(13) . . ?
C14 C19 C11 112.51(14) . . ?
C14 C19 C18 121.07(14) . . ?
C11 C19 C18 126.18(14) . . ?
O1A C2A C3A 107.94(13) . . ?
O1B C2B C3B 108.83(15) . . ?
O4C C4C O5C 124.59(14) . . ?
O4C C4C N4 123.93(14) . . ?
O5C C4C N4 111.46(13) . . ?
O5C C6C C9C 111.09(13) . . ?
O5C C6C C8C 102.18(13) . . ?
C9C C6C C8C 109.85(15) . . ?
O5C C6C C7C 109.41(13) . . ?
C9C C6C C7C 112.83(15) . . ?
C8C C6C C7C 110.99(16) . . ?

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
O1 P1 O1A C2A -40.03(13) . . . . ?
O1B P1 O1A C2A -165.26(11) . . . . ?
C2 P1 O1A C2A 87.40(12) . . . . ?
O1 P1 O1B C2B -41.48(14) . . . . ?
O1A P1 O1B C2B 84.18(13) . . . . ?
C2 P1 O1B C2B -165.85(12) . . . . ?
C10 N9 C2 C3 -109.65(15) . . . . ?
C10 N9 C2 P1 124.91(12) . . . . ?
O1 P1 C2 N9 75.90(12) . . . . ?
O1A P1 C2 N9 -52.59(11) . . . . ?
O1B P1 C2 N9 -158.97(10) . . . . ?
O1 P1 C2 C3 -47.61(13) . . . . ?
O1A P1 C2 C3 -176.10(10) . . . . ?
O1B P1 C2 C3 77.52(11) . . . . ?
C4C N4 C3 C8 140.28(14) . . . . ?
C5 N4 C3 C8 -51.97(17) . . . . ?
C4C N4 C3 C2 -94.58(16) . . . . ?
C5 N4 C3 C2 73.18(16) . . . . ?
N9 C2 C3 N4 50.20(15) . . . . ?
P1 C2 C3 N4 172.04(10) . . . . ?
N9 C2 C3 C8 172.89(12) . . . . ?
P1 C2 C3 C8 -65.27(15) . . . . ?
C4C N4 C5 C6 -140.45(15) . . . . ?
C3 N4 C5 C6 52.53(18) . . . . ?
N4 C5 C6 C7 -52.70(18) . . . . ?
C5 C6 C7 C8 55.84(18) . . . . ?
C6 C7 C8 C3 -56.57(17) . . . . ?
N4 C3 C8 C7 52.91(17) . . . . ?
C2 C3 C8 C7 -70.25(16) . . . . ?
C2 N9 C10 O10 -5.2(2) . . . . ?
C2 N9 C10 C11 175.55(13) . . . . ?
O10 C10 C11 C12 -152.96(16) . . . . ?
N9 C10 C11 C12 26.3(2) . . . . ?
O10 C10 C11 C19 25.7(2) . . . . ?
N9 C10 C11 C19 -155.04(14) . . . . ?
C19 C11 C12 S13 -0.46(18) . . . . ?
C10 C11 C12 S13 178.33(12) . . . . ?
C14 S13 C12 C11 0.29(13) . . . . ?
C12 S13 C14 C19 -0.04(14) . . . . ?
C12 S13 C14 C15 177.88(15) . . . . ?
C19 C14 C15 C16 -7.2(3) . . . . ?
S13 C14 C15 C16 175.17(13) . . . . ?
C14 C15 C16 C17 39.9(2) . . . . ?
C15 C16 C17 C18 -64.42(19) . . . . ?
C16 C17 C18 C19 51.49(19) . . . . ?
C15 C14 C19 C11 -178.03(16) . . . . ?
S13 C14 C19 C11 -0.21(18) . . . . ?
C15 C14 C19 C18 -3.3(3) . . . . ?
S13 C14 C19 C18 174.51(12) . . . . ?
C12 C11 C19 C14 0.4(2) . . . . ?
C10 C11 C19 C14 -178.37(14) . . . . ?
C12 C11 C19 C18 -173.96(15) . . . . ?
C10 C11 C19 C18 7.2(2) . . . . ?
C17 C18 C19 C14 -18.9(2) . . . . ?
C17 C18 C19 C11 155.04(16) . . . . ?
P1 O1A C2A C3A -137.78(12) . . . . ?
P1 O1B C2B C3B 127.93(14) . . . . ?
C6C O5C C4C O4C 5.2(2) . . . . ?
C6C O5C C4C N4 -175.99(13) . . . . ?
C3 N4 C4C O4C -6.1(2) . . . . ?
C5 N4 C4C O4C -173.06(15) . . . . ?
C3 N4 C4C O5C 175.10(13) . . . . ?
C5 N4 C4C O5C 8.2(2) . . . . ?
C4C O5C C6C C9C -63.26(19) . . . . ?
C4C O5C C6C C8C 179.64(15) . . . . ?
C4C O5C C6C C7C 61.96(19) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N9 H9 O1 0.869(14) 2.180(15) 2.9711(17) 151.3(15) 2_676 yes

_refine_diff_density_max         0.371
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.055

####################################################################### 
# 
# 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_4c-2
_database_code_depnum_ccdc_archive 'CCDC 2203661'
loop_
_audit_author_name
_audit_author_address
'Arto Valkonen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2022-08-26 deposited with the CCDC.	2023-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H33 N2 O6 P S'
_chemical_formula_sum            'C20 H33 N2 O6 P S'
_chemical_formula_weight         460.51

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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   12.7772(2)
_cell_length_b                   13.5168(2)
_cell_length_c                   13.6871(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.1990(10)
_cell_angle_gamma                90
_cell_volume                     2357.51(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    11871
_cell_measurement_theta_min      3.2060
_cell_measurement_theta_max      72.2300

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_F_000             984
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    2.179
_shelx_estimated_absorpt_T_min   0.561
_shelx_estimated_absorpt_T_max   0.750
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.403
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_reflns_number            21708
_diffrn_reflns_av_unetI/netI     0.0120
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.570
_diffrn_reflns_theta_max         69.981
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4473
_reflns_number_gt                3933
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    SHELXL-2018/3
_computing_publication_material  SHELXL-2018/3
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1177P)²+1.9054P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4473
_refine_ls_number_parameters     539
_refine_ls_number_restraints     284
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0780
_refine_ls_wR_factor_ref         0.2255
_refine_ls_wR_factor_gt          0.2175
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.163
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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 0.55172(17) 0.47154(12) 0.67277(11) 0.0454(4) Uani 0.5 1 d D U P A 1
O1 O 0.5675(5) 0.5596(3) 0.6111(3) 0.0647(12) Uani 0.5 1 d D . P A 1
O1A O 0.5502(10) 0.4877(10) 0.7844(7) 0.065(2) Uani 0.5 1 d D U P A 1
C2A C 0.6357(10) 0.5440(10) 0.8305(7) 0.103(3) Uani 0.5 1 d D U P A 1
H2A1 H 0.702678 0.519808 0.807383 0.124 Uiso 0.5 1 calc R U P A 1
H2A2 H 0.627579 0.614371 0.811482 0.124 Uiso 0.5 1 calc R U P A 1
C3A C 0.6389(11) 0.5361(13) 0.9329(8) 0.114(5) Uani 0.5 1 d D U P A 1
H3A1 H 0.697775 0.575066 0.962164 0.170 Uiso 0.5 1 calc R U P A 1
H3A2 H 0.573103 0.561013 0.956020 0.170 Uiso 0.5 1 calc R U P A 1
H3A3 H 0.648136 0.466533 0.951925 0.170 Uiso 0.5 1 calc R U P A 1
O1B O 0.6343(4) 0.3867(4) 0.6651(2) 0.0580(12) Uani 0.5 1 d D U P A 1
C2B C 0.6735(8) 0.3670(7) 0.5700(5) 0.081(2) Uani 0.5 1 d D U P A 1
H2B1 H 0.618589 0.379995 0.516656 0.097 Uiso 0.5 1 calc R U P A 1
H2B2 H 0.735413 0.408633 0.559595 0.097 Uiso 0.5 1 calc R U P A 1
C3B C 0.7014(11) 0.2640(9) 0.5731(8) 0.086(3) Uani 0.5 1 d D U P A 1
H3B1 H 0.728872 0.244815 0.510857 0.129 Uiso 0.5 1 calc R U P A 1
H3B2 H 0.755294 0.252639 0.626707 0.129 Uiso 0.5 1 calc R U P A 1
H3B3 H 0.639234 0.224188 0.584048 0.129 Uiso 0.5 1 calc R U P A 1
P1D P 0.50501(19) 0.45581(18) 0.65491(17) 0.0666(7) Uani 0.5 1 d D U P A 2
O1D O 0.5050(6) 0.5437(5) 0.5941(4) 0.094(2) Uani 0.5 1 d D U P A 2
O1E O 0.5295(10) 0.4820(12) 0.7670(7) 0.071(3) Uani 0.5 1 d D . P A 2
C2E C 0.5875(8) 0.5698(7) 0.8132(8) 0.088(3) Uani 0.5 1 d D . P A 2
H2E1 H 0.658618 0.573392 0.789187 0.106 Uiso 0.5 1 calc R U P A 2
H2E2 H 0.549730 0.631450 0.793657 0.106 Uiso 0.5 1 calc R U P A 2
C3E C 0.5957(8) 0.5618(10) 0.9165(8) 0.085(3) Uani 0.5 1 d D . P A 2
H3E1 H 0.633411 0.619285 0.944891 0.128 Uiso 0.5 1 calc R U P A 2
H3E2 H 0.525226 0.559226 0.940376 0.128 Uiso 0.5 1 calc R U P A 2
H3E3 H 0.633973 0.501243 0.935911 0.128 Uiso 0.5 1 calc R U P A 2
O1F O 0.5931(9) 0.3797(9) 0.6406(11) 0.195(6) Uani 0.5 1 d D U P A 2
C2F C 0.6887(11) 0.3616(15) 0.6024(15) 0.180(8) Uani 0.5 1 d D U P A 2
H2F1 H 0.744000 0.361827 0.656966 0.216 Uiso 0.5 1 calc R U P A 2
H2F2 H 0.703854 0.416884 0.558079 0.216 Uiso 0.5 1 calc R U P A 2
C3F C 0.696(2) 0.2713(17) 0.5498(19) 0.186(11) Uani 0.5 1 d D U P A 2
H3F1 H 0.766236 0.265494 0.525926 0.279 Uiso 0.5 1 calc R U P A 2
H3F2 H 0.683588 0.215581 0.593217 0.279 Uiso 0.5 1 calc R U P A 2
H3F3 H 0.643333 0.270787 0.494061 0.279 Uiso 0.5 1 calc R U P A 2
C2 C 0.4294(5) 0.4080(4) 0.6509(4) 0.0351(13) Uani 0.5 1 d D . P A 1
H2 H 0.419638 0.365574 0.709424 0.042 Uiso 0.5 1 calc R U P A 1
C3 C 0.3332(6) 0.4783(6) 0.6377(5) 0.0581(15) Uani 0.5 1 d D . P A 1
H3 H 0.340593 0.520311 0.578511 0.070 Uiso 0.5 1 calc R U P A 1
N4 N 0.2393(6) 0.4206(6) 0.6229(5) 0.0613(17) Uani 0.5 1 d D . P A 1
C5 C 0.1991(12) 0.3672(11) 0.7070(9) 0.079(4) Uani 0.5 1 d D . P A 1
H5A H 0.246835 0.311763 0.726191 0.095 Uiso 0.5 1 calc R U P A 1
H5B H 0.129074 0.339197 0.687310 0.095 Uiso 0.5 1 calc R U P A 1
C6 C 0.1907(7) 0.4366(9) 0.7944(7) 0.093(3) Uani 0.5 1 d D U P A 1
H6A H 0.133330 0.484467 0.778306 0.112 Uiso 0.5 1 calc R U P A 1
H6B H 0.171083 0.397086 0.851185 0.112 Uiso 0.5 1 calc R U P A 1
C8 C 0.3206(7) 0.5463(7) 0.7265(6) 0.078(3) Uani 0.5 1 d D U P A 1
H8A H 0.266506 0.596561 0.707511 0.093 Uiso 0.5 1 calc R U P A 1
H8B H 0.387613 0.581708 0.741622 0.093 Uiso 0.5 1 calc R U P A 1
C2D C 0.3873(5) 0.3830(4) 0.6491(4) 0.0376(13) Uani 0.5 1 d D . P A 2
H2D H 0.391669 0.337997 0.707268 0.045 Uiso 0.5 1 calc R U P A 2
C3D C 0.2846(6) 0.4405(4) 0.6500(4) 0.0383(12) Uani 0.5 1 d D . P A 2
H3D H 0.268451 0.467484 0.582541 0.046 Uiso 0.5 1 calc R U P A 2
N4D N 0.2024(7) 0.3697(5) 0.6687(5) 0.0408(14) Uani 0.5 1 d D . P A 2
C5D C 0.1994(5) 0.3323(4) 0.7692(4) 0.0499(13) Uani 0.5 1 d D . P A 2
H5D1 H 0.262247 0.291244 0.786213 0.060 Uiso 0.5 1 calc R U P A 2
H5D2 H 0.136462 0.290284 0.773958 0.060 Uiso 0.5 1 calc R U P A 2
C6D C 0.1962(6) 0.4192(6) 0.8410(5) 0.065(2) Uani 0.5 1 d D . P A 2
H6D1 H 0.203302 0.394254 0.909167 0.078 Uiso 0.5 1 calc R U P A 2
H6D2 H 0.128143 0.454041 0.830835 0.078 Uiso 0.5 1 calc R U P A 2
C8D C 0.2820(6) 0.5267(6) 0.7210(5) 0.0497(17) Uani 0.5 1 d D . P A 2
H8D1 H 0.341427 0.571758 0.711071 0.060 Uiso 0.5 1 calc R U P A 2
H8D2 H 0.216110 0.564350 0.707256 0.060 Uiso 0.5 1 calc R U P A 2
C7 C 0.2887(3) 0.4928(3) 0.8236(2) 0.0777(10) Uani 1 1 d D U . . .
H7A H 0.345073 0.447403 0.849130 0.093 Uiso 0.5 1 calc R U P A 1
H7B H 0.275896 0.542127 0.874897 0.093 Uiso 0.5 1 calc R U P A 1
H7C H 0.285023 0.550521 0.867812 0.093 Uiso 0.5 1 calc R U P A 2
H7D H 0.356822 0.459282 0.839096 0.093 Uiso 0.5 1 calc R U P A 2
N9 N 0.4324(4) 0.3430(4) 0.5669(4) 0.0400(12) Uani 0.5 1 d D . P A 1
H9 H 0.434(5) 0.370(4) 0.507(2) 0.048 Uiso 0.5 1 d D U P B 1
C10 C 0.403(2) 0.2442(9) 0.5661(10) 0.053(3) Uani 0.5 1 d D . P A 1
O10 O 0.4093(19) 0.2005(14) 0.6451(12) 0.064(3) Uani 0.5 1 d D . P A 1
C11 C 0.4093(15) 0.1867(13) 0.4724(11) 0.049(3) Uani 0.5 1 d D . P A 1
C12 C 0.4145(18) 0.2193(11) 0.3898(9) 0.070(4) Uani 0.5 1 d D . P A 1
H12 H 0.418876 0.288201 0.376903 0.085 Uiso 0.5 1 calc R U P A 1
S13 S 0.4133(4) 0.1289(2) 0.2950(3) 0.0637(7) Uani 0.5 1 d D . P A 1
C14 C 0.4303(8) 0.0333(8) 0.3886(9) 0.095(3) Uani 0.5 1 d D . P A 1
H14 H 0.448327 -0.033937 0.378491 0.114 Uiso 0.5 1 calc R U P A 1
C15 C 0.4135(10) 0.0729(8) 0.4693(11) 0.085(4) Uani 0.5 1 d D . P A 1
H15 H 0.403969 0.034166 0.525911 0.102 Uiso 0.5 1 calc R U P A 1
N9D N 0.3862(5) 0.3206(5) 0.5611(4) 0.0437(12) Uani 0.5 1 d D . P A 2
H9D H 0.374(5) 0.360(4) 0.508(3) 0.052 Uiso 0.5 1 d D U P C 2
C10D C 0.412(2) 0.2236(9) 0.5753(9) 0.051(3) Uani 0.5 1 d D . P A 2
O10D O 0.4017(18) 0.1791(13) 0.6509(12) 0.061(3) Uani 0.5 1 d D . P A 2
C11D C 0.403(2) 0.1720(16) 0.4779(13) 0.063(4) Uani 0.5 1 d D U P A 2
C12D C 0.3763(10) 0.0861(11) 0.4725(10) 0.084(3) Uani 0.5 1 d D U P A 2
H12D H 0.356671 0.048497 0.526886 0.101 Uiso 0.5 1 calc R U P A 2
S13D S 0.3778(3) 0.0401(3) 0.3566(2) 0.1064(9) Uani 0.5 1 d D U P A 2
C14D C 0.4044(14) 0.1541(8) 0.3030(11) 0.061(3) Uani 0.5 1 d D U P A 2
H14D H 0.410693 0.168049 0.235662 0.073 Uiso 0.5 1 calc R U P A 2
C15D C 0.4134(15) 0.2144(11) 0.3753(11) 0.068(3) Uani 0.5 1 d D U P A 2
H15D H 0.426167 0.282842 0.365642 0.081 Uiso 0.5 1 calc R U P A 2
C4C C 0.1959(6) 0.4088(5) 0.5265(4) 0.0530(13) Uani 0.5 1 d D . P A 1
O4C O 0.2298(4) 0.4506(3) 0.4572(3) 0.0711(12) Uani 0.5 1 d D . P A 1
O5C O 0.1157(7) 0.3487(6) 0.5216(7) 0.068(3) Uani 0.5 1 d D . P A 1
C6C C 0.0591(11) 0.330(2) 0.4258(9) 0.063(2) Uani 0.5 1 d D U P A 1
C7C C -0.0198(7) 0.2471(8) 0.4547(7) 0.107(3) Uani 0.5 1 d D U P A 1
H7C1 H 0.019742 0.190013 0.481805 0.160 Uiso 0.5 1 calc R U P A 1
H7C2 H -0.064568 0.273140 0.503802 0.160 Uiso 0.5 1 calc R U P A 1
H7C3 H -0.063511 0.226587 0.396373 0.160 Uiso 0.5 1 calc R U P A 1
C8C C 0.0056(7) 0.4161(7) 0.3852(6) 0.093(2) Uani 0.5 1 d D U P A 1
H8C1 H -0.030538 0.399321 0.321793 0.139 Uiso 0.5 1 calc R U P A 1
H8C2 H -0.045706 0.438890 0.430048 0.139 Uiso 0.5 1 calc R U P A 1
H8C3 H 0.056836 0.468714 0.376318 0.139 Uiso 0.5 1 calc R U P A 1
C9C C 0.1313(6) 0.2774(7) 0.3606(7) 0.089(2) Uani 0.5 1 d D U P A 1
H9C1 H 0.163115 0.220313 0.395406 0.134 Uiso 0.5 1 calc R U P A 1
H9C2 H 0.091115 0.254889 0.300977 0.134 Uiso 0.5 1 calc R U P A 1
H9C3 H 0.186517 0.322978 0.342999 0.134 Uiso 0.5 1 calc R U P A 1
C4G C 0.1294(4) 0.3336(3) 0.5983(3) 0.0407(10) Uani 0.5 1 d D . P A 2
O4G O 0.0643(3) 0.2729(3) 0.6144(3) 0.0645(11) Uani 0.5 1 d D . P A 2
O5G O 0.1387(7) 0.3769(6) 0.5105(5) 0.0492(17) Uani 0.5 1 d D . P A 2
C6G C 0.0776(11) 0.338(2) 0.4230(8) 0.057(2) Uani 0.5 1 d D U P A 2
C7G C -0.0402(6) 0.3536(6) 0.4346(6) 0.0782(19) Uani 0.5 1 d D U P A 2
H7G1 H -0.081042 0.327809 0.376758 0.117 Uiso 0.5 1 calc R U P A 2
H7G2 H -0.060291 0.318617 0.493134 0.117 Uiso 0.5 1 calc R U P A 2
H7G3 H -0.054386 0.424447 0.441406 0.117 Uiso 0.5 1 calc R U P A 2
C8G C 0.0992(5) 0.2304(4) 0.4085(4) 0.0537(12) Uani 0.5 1 d D U P A 2
H8G1 H 0.057745 0.206584 0.350126 0.080 Uiso 0.5 1 calc R U P A 2
H8G2 H 0.174012 0.220933 0.399941 0.080 Uiso 0.5 1 calc R U P A 2
H8G3 H 0.079953 0.193113 0.465952 0.080 Uiso 0.5 1 calc R U P A 2
C9G C 0.1178(7) 0.3995(6) 0.3418(4) 0.090(2) Uani 0.5 1 d D U P A 2
H9G1 H 0.082157 0.379697 0.278995 0.134 Uiso 0.5 1 calc R U P A 2
H9G2 H 0.103861 0.469576 0.353854 0.134 Uiso 0.5 1 calc R U P A 2
H9G3 H 0.193575 0.389309 0.339718 0.134 Uiso 0.5 1 calc R U P A 2


_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 1.482(4) . ?
P1 O1A 1.545(8) . ?
P1 O1B 1.567(5) . ?
P1 C2 1.790(6) . ?
O1A C2A 1.438(12) . ?
C2A C3A 1.402(12) . ?
C2A H2A1 0.9900 . ?
C2A H2A2 0.9900 . ?
C3A H3A1 0.9800 . ?
C3A H3A2 0.9800 . ?
C3A H3A3 0.9800 . ?
O1B C2B 1.454(6) . ?
C2B C3B 1.437(12) . ?
C2B H2B1 0.9900 . ?
C2B H2B2 0.9900 . ?
C3B H3B1 0.9800 . ?
C3B H3B2 0.9800 . ?
C3B H3B3 0.9800 . ?
P1D O1D 1.450(6) . ?
P1D O1F 1.548(7) . ?
P1D O1E 1.583(9) . ?
P1D C2D 1.794(7) . ?
O1E C2E 1.512(12) . ?
C2E C3E 1.415(12) . ?
C2E H2E1 0.9900 . ?
C2E H2E2 0.9900 . ?
C3E H3E1 0.9800 . ?
C3E H3E2 0.9800 . ?
C3E H3E3 0.9800 . ?
O1F C2F 1.386(8) . ?
C2F C3F 1.423(15) . ?
C2F H2F1 0.9900 . ?
C2F H2F2 0.9900 . ?
C3F H3F1 0.9800 . ?
C3F H3F2 0.9800 . ?
C3F H3F3 0.9800 . ?
C2 N9 1.450(8) . ?
C2 C3 1.553(8) . ?
C2 H2 1.0000 . ?
C3 N4 1.433(9) . ?
C3 C8 1.541(9) . ?
C3 H3 1.0000 . ?
N4 C4C 1.402(9) . ?
N4 C5 1.482(11) . ?
C5 C6 1.531(12) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.495(9) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C8 C7 1.592(10) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C2D N9D 1.469(8) . ?
C2D C3D 1.526(8) . ?
C2D H2D 1.0000 . ?
C3D N4D 1.458(10) . ?
C3D C8D 1.520(9) . ?
C3D H3D 1.0000 . ?
N4D C4G 1.379(10) . ?
N4D C5D 1.469(6) . ?
C5D C6D 1.534(9) . ?
C5D H5D1 0.9900 . ?
C5D H5D2 0.9900 . ?
C6D C7 1.577(8) . ?
C6D H6D1 0.9900 . ?
C6D H6D2 0.9900 . ?
C8D C7 1.474(8) . ?
C8D H8D1 0.9900 . ?
C8D H8D2 0.9900 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 H7C 0.9900 . ?
C7 H7D 0.9900 . ?
N9 C10 1.386(15) . ?
N9 H9 0.90(2) . ?
C10 O10 1.229(11) . ?
C10 C11 1.508(10) . ?
C11 C12 1.22(2) . ?
C11 C15 1.54(2) . ?
C12 S13 1.781(13) . ?
C12 H12 0.9500 . ?
S13 C14 1.822(10) . ?
C14 C15 1.259(17) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N9D C10D 1.363(13) . ?
N9D H9D 0.91(2) . ?
C10D O10D 1.214(12) . ?
C10D C11D 1.501(11) . ?
C11D C12D 1.21(2) . ?
C11D C15D 1.53(2) . ?
C12D S13D 1.706(13) . ?
C12D H12D 0.9500 . ?
S13D C14D 1.750(13) . ?
C14D C15D 1.281(19) . ?
C14D H14D 0.9500 . ?
C15D H15D 0.9500 . ?
C4C O4C 1.211(7) . ?
C4C O5C 1.304(9) . ?
O5C C6C 1.474(11) . ?
C6C C8C 1.44(3) . ?
C6C C9C 1.51(2) . ?
C6C C7C 1.575(19) . ?
C7C H7C1 0.9800 . ?
C7C H7C2 0.9800 . ?
C7C H7C3 0.9800 . ?
C8C H8C1 0.9800 . ?
C8C H8C2 0.9800 . ?
C8C H8C3 0.9800 . ?
C9C H9C1 0.9800 . ?
C9C H9C2 0.9800 . ?
C9C H9C3 0.9800 . ?
C4G O4G 1.201(6) . ?
C4G O5G 1.350(8) . ?
O5G C6G 1.478(10) . ?
C6G C8G 1.49(3) . ?
C6G C9G 1.510(17) . ?
C6G C7G 1.541(17) . ?
C7G H7G1 0.9800 . ?
C7G H7G2 0.9800 . ?
C7G H7G3 0.9800 . ?
C8G H8G1 0.9800 . ?
C8G H8G2 0.9800 . ?
C8G H8G3 0.9800 . ?
C9G H9G1 0.9800 . ?
C9G H9G2 0.9800 . ?
C9G H9G3 0.9800 . ?

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 O1A 117.5(6) . . ?
O1 P1 O1B 115.4(3) . . ?
O1A P1 O1B 103.1(6) . . ?
O1 P1 C2 116.4(3) . . ?
O1A P1 C2 99.2(5) . . ?
O1B P1 C2 102.8(3) . . ?
C2A O1A P1 116.4(8) . . ?
C3A C2A O1A 111.4(9) . . ?
C3A C2A H2A1 109.4 . . ?
O1A C2A H2A1 109.4 . . ?
C3A C2A H2A2 109.4 . . ?
O1A C2A H2A2 109.4 . . ?
H2A1 C2A H2A2 108.0 . . ?
C2A C3A H3A1 109.5 . . ?
C2A C3A H3A2 109.5 . . ?
H3A1 C3A H3A2 109.5 . . ?
C2A C3A H3A3 109.5 . . ?
H3A1 C3A H3A3 109.5 . . ?
H3A2 C3A H3A3 109.5 . . ?
C2B O1B P1 118.1(4) . . ?
C3B C2B O1B 104.6(7) . . ?
C3B C2B H2B1 110.8 . . ?
O1B C2B H2B1 110.8 . . ?
C3B C2B H2B2 110.8 . . ?
O1B C2B H2B2 110.8 . . ?
H2B1 C2B H2B2 108.9 . . ?
C2B C3B H3B1 109.5 . . ?
C2B C3B H3B2 109.5 . . ?
H3B1 C3B H3B2 109.5 . . ?
C2B C3B H3B3 109.5 . . ?
H3B1 C3B H3B3 109.5 . . ?
H3B2 C3B H3B3 109.5 . . ?
O1D P1D O1F 116.1(6) . . ?
O1D P1D O1E 111.4(6) . . ?
O1F P1D O1E 100.2(8) . . ?
O1D P1D C2D 117.3(4) . . ?
O1F P1D C2D 104.2(5) . . ?
O1E P1D C2D 105.7(5) . . ?
C2E O1E P1D 129.5(10) . . ?
C3E C2E O1E 110.8(9) . . ?
C3E C2E H2E1 109.5 . . ?
O1E C2E H2E1 109.5 . . ?
C3E C2E H2E2 109.5 . . ?
O1E C2E H2E2 109.5 . . ?
H2E1 C2E H2E2 108.1 . . ?
C2E C3E H3E1 109.5 . . ?
C2E C3E H3E2 109.5 . . ?
H3E1 C3E H3E2 109.5 . . ?
C2E C3E H3E3 109.5 . . ?
H3E1 C3E H3E3 109.5 . . ?
H3E2 C3E H3E3 109.5 . . ?
C2F O1F P1D 146.6(13) . . ?
O1F C2F C3F 115.8(16) . . ?
O1F C2F H2F1 108.3 . . ?
C3F C2F H2F1 108.3 . . ?
O1F C2F H2F2 108.3 . . ?
C3F C2F H2F2 108.3 . . ?
H2F1 C2F H2F2 107.4 . . ?
C2F C3F H3F1 109.5 . . ?
C2F C3F H3F2 109.5 . . ?
H3F1 C3F H3F2 109.5 . . ?
C2F C3F H3F3 109.5 . . ?
H3F1 C3F H3F3 109.5 . . ?
H3F2 C3F H3F3 109.5 . . ?
N9 C2 C3 110.2(5) . . ?
N9 C2 P1 110.5(4) . . ?
C3 C2 P1 113.5(5) . . ?
N9 C2 H2 107.4 . . ?
C3 C2 H2 107.4 . . ?
P1 C2 H2 107.4 . . ?
N4 C3 C8 107.5(7) . . ?
N4 C3 C2 109.3(6) . . ?
C8 C3 C2 113.7(5) . . ?
N4 C3 H3 108.7 . . ?
C8 C3 H3 108.7 . . ?
C2 C3 H3 108.7 . . ?
C4C N4 C3 117.7(7) . . ?
C4C N4 C5 122.6(9) . . ?
C3 N4 C5 119.3(8) . . ?
N4 C5 C6 110.9(10) . . ?
N4 C5 H5A 109.5 . . ?
C6 C5 H5A 109.5 . . ?
N4 C5 H5B 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 108.0 . . ?
C7 C6 C5 114.5(8) . . ?
C7 C6 H6A 108.6 . . ?
C5 C6 H6A 108.6 . . ?
C7 C6 H6B 108.6 . . ?
C5 C6 H6B 108.6 . . ?
H6A C6 H6B 107.6 . . ?
C3 C8 C7 115.8(7) . . ?
C3 C8 H8A 108.3 . . ?
C7 C8 H8A 108.3 . . ?
C3 C8 H8B 108.3 . . ?
C7 C8 H8B 108.3 . . ?
H8A C8 H8B 107.4 . . ?
N9D C2D C3D 110.0(5) . . ?
N9D C2D P1D 108.0(4) . . ?
C3D C2D P1D 116.0(4) . . ?
N9D C2D H2D 107.5 . . ?
C3D C2D H2D 107.5 . . ?
P1D C2D H2D 107.5 . . ?
N4D C3D C8D 110.0(5) . . ?
N4D C3D C2D 107.3(5) . . ?
C8D C3D C2D 117.1(6) . . ?
N4D C3D H3D 107.4 . . ?
C8D C3D H3D 107.4 . . ?
C2D C3D H3D 107.4 . . ?
C4G N4D C3D 124.7(6) . . ?
C4G N4D C5D 118.0(6) . . ?
C3D N4D C5D 117.4(7) . . ?
N4D C5D C6D 109.9(6) . . ?
N4D C5D H5D1 109.7 . . ?
C6D C5D H5D1 109.7 . . ?
N4D C5D H5D2 109.7 . . ?
C6D C5D H5D2 109.7 . . ?
H5D1 C5D H5D2 108.2 . . ?
C5D C6D C7 109.4(5) . . ?
C5D C6D H6D1 109.8 . . ?
C7 C6D H6D1 109.8 . . ?
C5D C6D H6D2 109.8 . . ?
C7 C6D H6D2 109.8 . . ?
H6D1 C6D H6D2 108.2 . . ?
C7 C8D C3D 111.6(5) . . ?
C7 C8D H8D1 109.3 . . ?
C3D C8D H8D1 109.3 . . ?
C7 C8D H8D2 109.3 . . ?
C3D C8D H8D2 109.3 . . ?
H8D1 C8D H8D2 108.0 . . ?
C8D C7 C6D 110.4(4) . . ?
C6 C7 C8 105.5(6) . . ?
C6 C7 H7A 110.6 . . ?
C8 C7 H7A 110.6 . . ?
C6 C7 H7B 110.6 . . ?
C8 C7 H7B 110.6 . . ?
H7A C7 H7B 108.8 . . ?
C8D C7 H7C 109.6 . . ?
C6D C7 H7C 109.6 . . ?
C8D C7 H7D 109.6 . . ?
C6D C7 H7D 109.6 . . ?
H7C C7 H7D 108.1 . . ?
C10 N9 C2 124.5(7) . . ?
C10 N9 H9 114(4) . . ?
C2 N9 H9 118(4) . . ?
O10 C10 N9 117.1(14) . . ?
O10 C10 C11 119.7(13) . . ?
N9 C10 C11 118.1(13) . . ?
C12 C11 C10 127.7(15) . . ?
C12 C11 C15 109.4(8) . . ?
C10 C11 C15 122.9(14) . . ?
C11 C12 S13 115.4(12) . . ?
C11 C12 H12 122.3 . . ?
S13 C12 H12 122.3 . . ?
C12 S13 C14 88.9(7) . . ?
C15 C14 S13 107.2(9) . . ?
C15 C14 H14 126.4 . . ?
S13 C14 H14 126.4 . . ?
C14 C15 C11 117.2(12) . . ?
C14 C15 H15 121.4 . . ?
C11 C15 H15 121.4 . . ?
C10D N9D C2D 116.6(7) . . ?
C10D N9D H9D 135(4) . . ?
C2D N9D H9D 108(4) . . ?
O10D C10D N9D 123.8(15) . . ?
O10D C10D C11D 121.3(16) . . ?
N9D C10D C11D 108.5(13) . . ?
C12D C11D C10D 120.2(19) . . ?
C12D C11D C15D 110.3(11) . . ?
C10D C11D C15D 129.3(17) . . ?
C11D C12D S13D 112.6(12) . . ?
C11D C12D H12D 123.7 . . ?
S13D C12D H12D 123.7 . . ?
C12D S13D C14D 94.8(7) . . ?
C15D C14D S13D 104.2(11) . . ?
C15D C14D H14D 127.9 . . ?
S13D C14D H14D 127.9 . . ?
C14D C15D C11D 117.5(14) . . ?
C14D C15D H15D 121.3 . . ?
C11D C15D H15D 121.3 . . ?
O4C C4C O5C 125.2(7) . . ?
O4C C4C N4 122.9(8) . . ?
O5C C4C N4 112.0(8) . . ?
C4C O5C C6C 119.1(10) . . ?
C8C C6C O5C 113.0(17) . . ?
C8C C6C C9C 116.5(12) . . ?
O5C C6C C9C 109.0(13) . . ?
C8C C6C C7C 112.2(12) . . ?
O5C C6C C7C 100.4(12) . . ?
C9C C6C C7C 104.2(17) . . ?
C6C C7C H7C1 109.5 . . ?
C6C C7C H7C2 109.5 . . ?
H7C1 C7C H7C2 109.5 . . ?
C6C C7C H7C3 109.5 . . ?
H7C1 C7C H7C3 109.5 . . ?
H7C2 C7C H7C3 109.5 . . ?
C6C C8C H8C1 109.5 . . ?
C6C C8C H8C2 109.5 . . ?
H8C1 C8C H8C2 109.5 . . ?
C6C C8C H8C3 109.5 . . ?
H8C1 C8C H8C3 109.5 . . ?
H8C2 C8C H8C3 109.5 . . ?
C6C C9C H9C1 109.5 . . ?
C6C C9C H9C2 109.5 . . ?
H9C1 C9C H9C2 109.5 . . ?
C6C C9C H9C3 109.5 . . ?
H9C1 C9C H9C3 109.5 . . ?
H9C2 C9C H9C3 109.5 . . ?
O4G C4G O5G 124.5(5) . . ?
O4G C4G N4D 123.8(5) . . ?
O5G C4G N4D 111.7(5) . . ?
C4G O5G C6G 119.4(9) . . ?
O5G C6G C8G 111.3(15) . . ?
O5G C6G C9G 102.2(10) . . ?
C8G C6G C9G 111.3(11) . . ?
O5G C6G C7G 109.2(11) . . ?
C8G C6G C7G 109.8(10) . . ?
C9G C6G C7G 112.8(16) . . ?
C6G C7G H7G1 109.5 . . ?
C6G C7G H7G2 109.5 . . ?
H7G1 C7G H7G2 109.5 . . ?
C6G C7G H7G3 109.5 . . ?
H7G1 C7G H7G3 109.5 . . ?
H7G2 C7G H7G3 109.5 . . ?
C6G C8G H8G1 109.5 . . ?
C6G C8G H8G2 109.5 . . ?
H8G1 C8G H8G2 109.5 . . ?
C6G C8G H8G3 109.5 . . ?
H8G1 C8G H8G3 109.5 . . ?
H8G2 C8G H8G3 109.5 . . ?
C6G C9G H9G1 109.5 . . ?
C6G C9G H9G2 109.5 . . ?
H9G1 C9G H9G2 109.5 . . ?
C6G C9G H9G3 109.5 . . ?
H9G1 C9G H9G3 109.5 . . ?
H9G2 C9G H9G3 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
O1 P1 O1A C2A -50.0(14) . . . . ?
O1B P1 O1A C2A 78.3(12) . . . . ?
C2 P1 O1A C2A -176.2(11) . . . . ?
P1 O1A C2A C3A -167.2(12) . . . . ?
O1 P1 O1B C2B -36.9(8) . . . . ?
O1A P1 O1B C2B -166.5(8) . . . . ?
C2 P1 O1B C2B 90.8(7) . . . . ?
P1 O1B C2B C3B -152.3(8) . . . . ?
O1D P1D O1E C2E -24.2(15) . . . . ?
O1F P1D O1E C2E 99.3(14) . . . . ?
C2D P1D O1E C2E -152.7(12) . . . . ?
P1D O1E C2E C3E -177.3(11) . . . . ?
O1D P1D O1F C2F 15(3) . . . . ?
O1E P1D O1F C2F -105(3) . . . . ?
C2D P1D O1F C2F 146(3) . . . . ?
P1D O1F C2F C3F -134(2) . . . . ?
O1 P1 C2 N9 80.9(5) . . . . ?
O1A P1 C2 N9 -152.1(7) . . . . ?
O1B P1 C2 N9 -46.3(4) . . . . ?
O1 P1 C2 C3 -43.5(5) . . . . ?
O1A P1 C2 C3 83.5(7) . . . . ?
O1B P1 C2 C3 -170.7(4) . . . . ?
N9 C2 C3 N4 56.7(7) . . . . ?
P1 C2 C3 N4 -178.7(4) . . . . ?
N9 C2 C3 C8 176.8(7) . . . . ?
P1 C2 C3 C8 -58.6(8) . . . . ?
C8 C3 N4 C4C 136.5(6) . . . . ?
C2 C3 N4 C4C -99.7(6) . . . . ?
C8 C3 N4 C5 -50.3(10) . . . . ?
C2 C3 N4 C5 73.5(9) . . . . ?
C4C N4 C5 C6 -136.2(9) . . . . ?
C3 N4 C5 C6 51.0(13) . . . . ?
N4 C5 C6 C7 -52.3(15) . . . . ?
N4 C3 C8 C7 52.6(7) . . . . ?
C2 C3 C8 C7 -68.6(9) . . . . ?
O1D P1D C2D N9D 80.3(5) . . . . ?
O1F P1D C2D N9D -49.6(7) . . . . ?
O1E P1D C2D N9D -154.8(7) . . . . ?
O1D P1D C2D C3D -43.7(6) . . . . ?
O1F P1D C2D C3D -173.6(7) . . . . ?
O1E P1D C2D C3D 81.2(8) . . . . ?
N9D C2D C3D N4D 70.6(7) . . . . ?
P1D C2D C3D N4D -166.5(5) . . . . ?
N9D C2D C3D C8D -165.3(5) . . . . ?
P1D C2D C3D C8D -42.4(6) . . . . ?
C8D C3D N4D C4G 128.2(7) . . . . ?
C2D C3D N4D C4G -103.4(8) . . . . ?
C8D C3D N4D C5D -53.6(9) . . . . ?
C2D C3D N4D C5D 74.7(8) . . . . ?
C4G N4D C5D C6D -127.9(6) . . . . ?
C3D N4D C5D C6D 53.8(9) . . . . ?
N4D C5D C6D C7 -52.3(8) . . . . ?
N4D C3D C8D C7 54.7(8) . . . . ?
C2D C3D C8D C7 -68.1(7) . . . . ?
C3D C8D C7 C6D -57.8(7) . . . . ?
C5 C6 C7 C8 53.4(11) . . . . ?
C5D C6D C7 C8D 56.7(7) . . . . ?
C3 C8 C7 C6 -55.1(8) . . . . ?
C3 C2 N9 C10 -103.5(15) . . . . ?
P1 C2 N9 C10 130.2(14) . . . . ?
C2 N9 C10 O10 -26(3) . . . . ?
C2 N9 C10 C11 179.3(13) . . . . ?
O10 C10 C11 C12 -172(3) . . . . ?
N9 C10 C11 C12 -18(4) . . . . ?
O10 C10 C11 C15 6(4) . . . . ?
N9 C10 C11 C15 159.9(16) . . . . ?
C10 C11 C12 S13 -176(2) . . . . ?
C15 C11 C12 S13 5(2) . . . . ?
C11 C12 S13 C14 -10.5(18) . . . . ?
C12 S13 C14 C15 12.8(12) . . . . ?
S13 C14 C15 C11 -13.1(15) . . . . ?
C12 C11 C15 C14 6(2) . . . . ?
C10 C11 C15 C14 -172.5(19) . . . . ?
C3D C2D N9D C10D -129.9(15) . . . . ?
P1D C2D N9D C10D 102.6(15) . . . . ?
C2D N9D C10D O10D 26(3) . . . . ?
C2D N9D C10D C11D 177.9(15) . . . . ?
O10D C10D C11D C12D 6(4) . . . . ?
N9D C10D C11D C12D -147(2) . . . . ?
O10D C10D C11D C15D 180(3) . . . . ?
N9D C10D C11D C15D 27(4) . . . . ?
C10D C11D C12D S13D -176.4(19) . . . . ?
C15D C11D C12D S13D 8(2) . . . . ?
C11D C12D S13D C14D -6.8(18) . . . . ?
C12D S13D C14D C15D 2.3(15) . . . . ?
S13D C14D C15D C11D 2(2) . . . . ?
C12D C11D C15D C14D -7(3) . . . . ?
C10D C11D C15D C14D 178(2) . . . . ?
C3 N4 C4C O4C -5.4(9) . . . . ?
C5 N4 C4C O4C -178.4(9) . . . . ?
C3 N4 C4C O5C 174.9(7) . . . . ?
C5 N4 C4C O5C 2.0(12) . . . . ?
O4C C4C O5C C6C -1.1(18) . . . . ?
N4 C4C O5C C6C 178.5(14) . . . . ?
C4C O5C C6C C8C -66.1(14) . . . . ?
C4C O5C C6C C9C 65(2) . . . . ?
C4C O5C C6C C7C 174.2(10) . . . . ?
C3D N4D C4G O4G 177.5(6) . . . . ?
C5D N4D C4G O4G -0.7(10) . . . . ?
C3D N4D C4G O5G -4.1(10) . . . . ?
C5D N4D C4G O5G 177.7(7) . . . . ?
O4G C4G O5G C6G -10.4(16) . . . . ?
N4D C4G O5G C6G 171.2(13) . . . . ?
C4G O5G C6G C8G -56.1(12) . . . . ?
C4G O5G C6G C9G -175.0(10) . . . . ?
C4G O5G C6G C7G 65(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N9 H9 O1 0.90(2) 1.87(2) 2.769(7) 174(5) 3_666 yes
N9D H9D O1D 0.91(2) 2.52(5) 3.200(8) 132(5) 3_666 yes

_refine_diff_density_max         0.995
_refine_diff_density_min         -0.598
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_4f-1
_database_code_depnum_ccdc_archive 'CCDC 2203664'
loop_
_audit_author_name
_audit_author_address
'Arto Valkonen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2022-08-26 deposited with the CCDC.	2023-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H39 N2 O6 P S, H2 O'
_chemical_formula_sum            'C24 H41 N2 O7 P S'
_chemical_formula_weight         532.62

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'
S S 0.1246 0.1234 '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'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.9060(3)
_cell_length_b                   12.7308(4)
_cell_length_c                   13.1186(4)
_cell_angle_alpha                73.251(3)
_cell_angle_beta                 76.379(3)
_cell_angle_gamma                73.533(3)
_cell_volume                     1346.58(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    20994
_cell_measurement_theta_min      2.6380
_cell_measurement_theta_max      29.7990

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_F_000             572
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.224
_shelx_estimated_absorpt_T_min   0.926
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.622
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0107
_diffrn_reflns_number            39668
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.419
_diffrn_reflns_theta_max         30.024
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7272
_reflns_number_gt                6425
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    SHELXL-2019/2
_computing_publication_material  SHELXL-2019/2
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0364P)²+0.6436P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7272
_refine_ls_number_parameters     325
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0390
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0860
_refine_ls_wR_factor_gt          0.0819
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S12 S 0.66440(3) 0.21436(2) 0.27372(2) 0.01940(7) Uani 1 1 d . . . . .
P1 P 0.15951(3) 0.52693(2) 0.19519(2) 0.01621(7) Uani 1 1 d . . . . .
O1 O 0.26074(10) 0.55668(7) 0.08940(7) 0.02066(17) Uani 1 1 d . . . . .
O10 O 0.29481(10) 0.32150(7) 0.48067(7) 0.02380(19) Uani 1 1 d . . . . .
O1A O -0.00104(10) 0.61284(8) 0.21879(8) 0.0260(2) Uani 1 1 d . . . . .
O1B O 0.10611(10) 0.41401(8) 0.21412(7) 0.02338(19) Uani 1 1 d . . . . .
O4C O 0.04263(10) 0.88369(7) 0.22002(7) 0.02218(18) Uani 1 1 d . . . . .
O5C O 0.28329(10) 0.78707(7) 0.14838(6) 0.01775(16) Uani 1 1 d . . . . .
N4 N 0.16736(11) 0.71392(8) 0.31435(7) 0.01548(18) Uani 1 1 d . . . . .
N9 N 0.38606(11) 0.41213(8) 0.31079(8) 0.01597(18) Uani 1 1 d D . . . .
H9 H 0.4664(16) 0.4202(12) 0.2584(11) 0.019 Uiso 1 1 d D U . . .
C2 C 0.25011(13) 0.50882(9) 0.31149(9) 0.0146(2) Uani 1 1 d . . . . .
H2 H 0.171336 0.487730 0.377447 0.018 Uiso 1 1 calc R U . . .
C3 C 0.29847(13) 0.61331(9) 0.32099(9) 0.0143(2) Uani 1 1 d . . . . .
H3 H 0.386804 0.629894 0.260276 0.017 Uiso 1 1 calc R U . . .
C5 C 0.03649(13) 0.71376(10) 0.40665(9) 0.0176(2) Uani 1 1 d . . . . .
H5A H -0.017246 0.653388 0.412934 0.021 Uiso 1 1 calc R U . . .
H5B H -0.042306 0.786826 0.394628 0.021 Uiso 1 1 calc R U . . .
C6 C 0.09838(15) 0.69469(10) 0.51087(9) 0.0207(2) Uani 1 1 d . . . . .
H6A H 0.010050 0.689820 0.572792 0.025 Uiso 1 1 calc R U . . .
H6B H 0.142172 0.759071 0.507764 0.025 Uiso 1 1 calc R U . . .
C7 C 0.22750(15) 0.58586(10) 0.52664(9) 0.0211(2) Uani 1 1 d . . . . .
H7A H 0.180558 0.520646 0.538462 0.025 Uiso 1 1 calc R U . . .
H7B H 0.273078 0.577085 0.591358 0.025 Uiso 1 1 calc R U . . .
C8 C 0.35914(14) 0.58770(10) 0.42756(9) 0.0183(2) Uani 1 1 d . . . . .
H8A H 0.435793 0.513517 0.436910 0.022 Uiso 1 1 calc R U . . .
H8B H 0.416688 0.645287 0.423407 0.022 Uiso 1 1 calc R U . . .
C10 C 0.39780(13) 0.32358(9) 0.39965(9) 0.0159(2) Uani 1 1 d . . . . .
C11 C 0.53876(13) 0.22891(9) 0.39378(9) 0.0156(2) Uani 1 1 d . . . . .
C13 C 0.77945(14) 0.09103(10) 0.33617(10) 0.0211(2) Uani 1 1 d . . . . .
H13 H 0.870468 0.047960 0.299763 0.025 Uiso 1 1 calc R U . . .
C14 C 0.72500(14) 0.06173(9) 0.44465(10) 0.0178(2) Uani 1 1 d . . . . .
C15 C 0.80163(15) -0.04061(10) 0.52294(10) 0.0227(2) Uani 1 1 d . . . . .
H15A H 0.918363 -0.056780 0.500208 0.027 Uiso 1 1 calc R U . . .
H15B H 0.764278 -0.106845 0.523036 0.027 Uiso 1 1 calc R U . . .
C16 C 0.75952(16) -0.01995(11) 0.63643(11) 0.0262(3) Uani 1 1 d . . . . .
H16A H 0.802746 -0.089371 0.688583 0.031 Uiso 1 1 calc R U . . .
H16B H 0.807270 0.040687 0.638401 0.031 Uiso 1 1 calc R U . . .
C17 C 0.57963(16) 0.01399(10) 0.66758(10) 0.0237(2) Uani 1 1 d . . . . .
H17A H 0.552655 0.019692 0.743742 0.028 Uiso 1 1 calc R U . . .
H17B H 0.532618 -0.045391 0.661786 0.028 Uiso 1 1 calc R U . . .
C18 C 0.50722(15) 0.12674(10) 0.59580(9) 0.0201(2) Uani 1 1 d . . . . .
H18A H 0.392541 0.132544 0.601133 0.024 Uiso 1 1 calc R U . . .
H18B H 0.517739 0.188982 0.622707 0.024 Uiso 1 1 calc R U . . .
C19 C 0.58517(13) 0.14039(9) 0.47876(9) 0.0159(2) Uani 1 1 d . . . . .
C2A C -0.13820(16) 0.63127(16) 0.16855(13) 0.0386(4) Uani 1 1 d . . . . .
H2A1 H -0.168143 0.559074 0.179757 0.046 Uiso 1 1 calc R U . . .
H2A2 H -0.113716 0.663446 0.089941 0.046 Uiso 1 1 calc R U . . .
C3A C -0.27061(17) 0.71125(14) 0.21986(13) 0.0373(3) Uani 1 1 d . . . . .
H3A1 H -0.365380 0.725548 0.187667 0.056 Uiso 1 1 calc R U . . .
H3A2 H -0.293859 0.678425 0.297553 0.056 Uiso 1 1 calc R U . . .
H3A3 H -0.239660 0.782361 0.208113 0.056 Uiso 1 1 calc R U . . .
C2B C 0.18963(16) 0.32675(11) 0.15673(11) 0.0262(3) Uani 1 1 d . . . . .
H2B1 H 0.267946 0.269504 0.198537 0.031 Uiso 1 1 calc R U . . .
H2B2 H 0.246749 0.359799 0.085484 0.031 Uiso 1 1 calc R U . . .
C3B C 0.06794(19) 0.27378(12) 0.14265(12) 0.0323(3) Uani 1 1 d . . . . .
H3B1 H 0.120512 0.214188 0.103997 0.048 Uiso 1 1 calc R U . . .
H3B2 H 0.012399 0.241291 0.213659 0.048 Uiso 1 1 calc R U . . .
H3B3 H -0.008708 0.331204 0.101084 0.048 Uiso 1 1 calc R U . . .
C4C C 0.15453(13) 0.80185(9) 0.22644(9) 0.0160(2) Uani 1 1 d . . . . .
C6C C 0.28438(14) 0.86416(10) 0.04024(9) 0.0180(2) Uani 1 1 d . . . . .
C7C C 0.27965(16) 0.98263(10) 0.04689(10) 0.0248(3) Uani 1 1 d . . . . .
H7C1 H 0.280411 1.033238 -0.025327 0.037 Uiso 1 1 calc R U . . .
H7C2 H 0.182765 1.009791 0.094849 0.037 Uiso 1 1 calc R U . . .
H7C3 H 0.372737 0.981059 0.075441 0.037 Uiso 1 1 calc R U . . .
C8C C 0.44347(15) 0.81342(11) -0.02126(10) 0.0236(2) Uani 1 1 d . . . . .
H8C1 H 0.457280 0.858699 -0.095708 0.035 Uiso 1 1 calc R U . . .
H8C2 H 0.529382 0.812878 0.013947 0.035 Uiso 1 1 calc R U . . .
H8C3 H 0.446133 0.736036 -0.021598 0.035 Uiso 1 1 calc R U . . .
C9C C 0.14837(15) 0.86004(11) -0.00924(10) 0.0229(2) Uani 1 1 d . . . . .
H9C1 H 0.149703 0.911433 -0.081092 0.034 Uiso 1 1 calc R U . . .
H9C2 H 0.160691 0.783033 -0.015431 0.034 Uiso 1 1 calc R U . . .
H9C3 H 0.047170 0.882992 0.036946 0.034 Uiso 1 1 calc R U . . .
O20 O 0.58954(12) 0.50279(9) 0.11199(7) 0.0268(2) Uani 1 1 d D . . . .
H20A H 0.647(2) 0.4767(15) 0.0605(13) 0.040 Uiso 1 1 d D U . . .
H20B H 0.5009(18) 0.5334(15) 0.0909(14) 0.040 Uiso 1 1 d D U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S12 C13 1.7111(12) . ?
S12 C11 1.7285(11) . ?
P1 O1 1.4776(9) . ?
P1 O1A 1.5610(9) . ?
P1 O1B 1.5749(9) . ?
P1 C2 1.8176(11) . ?
O10 C10 1.2289(14) . ?
O1A C2A 1.4523(15) . ?
O1B C2B 1.4506(14) . ?
O4C C4C 1.2191(14) . ?
O5C C4C 1.3545(13) . ?
O5C C6C 1.4739(13) . ?
N4 C4C 1.3571(14) . ?
N4 C3 1.4654(13) . ?
N4 C5 1.4697(14) . ?
N9 C10 1.3688(14) . ?
N9 C2 1.4621(14) . ?
N9 H9 0.874(12) . ?
C2 C3 1.5545(15) . ?
C2 H2 1.0000 . ?
C3 C8 1.5315(15) . ?
C3 H3 1.0000 . ?
C5 C6 1.5230(16) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.5259(17) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.5313(16) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C10 C11 1.4781(15) . ?
C11 C19 1.3829(15) . ?
C13 C14 1.3678(17) . ?
C13 H13 0.9500 . ?
C14 C19 1.4293(15) . ?
C14 C15 1.5077(16) . ?
C15 C16 1.5274(18) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.5236(19) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.5314(16) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.5106(16) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C2A C3A 1.490(2) . ?
C2A H2A1 0.9900 . ?
C2A H2A2 0.9900 . ?
C3A H3A1 0.9800 . ?
C3A H3A2 0.9800 . ?
C3A H3A3 0.9800 . ?
C2B C3B 1.4979(18) . ?
C2B H2B1 0.9900 . ?
C2B H2B2 0.9900 . ?
C3B H3B1 0.9800 . ?
C3B H3B2 0.9800 . ?
C3B H3B3 0.9800 . ?
C6C C9C 1.5223(17) . ?
C6C C8C 1.5228(16) . ?
C6C C7C 1.5239(16) . ?
C7C H7C1 0.9800 . ?
C7C H7C2 0.9800 . ?
C7C H7C3 0.9800 . ?
C8C H8C1 0.9800 . ?
C8C H8C2 0.9800 . ?
C8C H8C3 0.9800 . ?
C9C H9C1 0.9800 . ?
C9C H9C2 0.9800 . ?
C9C H9C3 0.9800 . ?
O20 H20A 0.837(14) . ?
O20 H20B 0.848(14) . ?

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
C13 S12 C11 91.94(6) . . ?
O1 P1 O1A 117.05(5) . . ?
O1 P1 O1B 113.45(5) . . ?
O1A P1 O1B 102.89(5) . . ?
O1 P1 C2 114.89(5) . . ?
O1A P1 C2 101.89(5) . . ?
O1B P1 C2 105.05(5) . . ?
C2A O1A P1 124.12(8) . . ?
C2B O1B P1 123.57(8) . . ?
C4C O5C C6C 120.04(9) . . ?
C4C N4 C3 124.33(9) . . ?
C4C N4 C5 118.77(9) . . ?
C3 N4 C5 116.72(9) . . ?
C10 N9 C2 120.04(9) . . ?
C10 N9 H9 121.8(10) . . ?
C2 N9 H9 116.8(10) . . ?
N9 C2 C3 111.26(9) . . ?
N9 C2 P1 107.04(7) . . ?
C3 C2 P1 116.54(7) . . ?
N9 C2 H2 107.2 . . ?
C3 C2 H2 107.2 . . ?
P1 C2 H2 107.2 . . ?
N4 C3 C8 109.19(9) . . ?
N4 C3 C2 112.61(9) . . ?
C8 C3 C2 110.12(9) . . ?
N4 C3 H3 108.3 . . ?
C8 C3 H3 108.3 . . ?
C2 C3 H3 108.3 . . ?
N4 C5 C6 110.67(9) . . ?
N4 C5 H5A 109.5 . . ?
C6 C5 H5A 109.5 . . ?
N4 C5 H5B 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C5 C6 C7 109.98(9) . . ?
C5 C6 H6A 109.7 . . ?
C7 C6 H6A 109.7 . . ?
C5 C6 H6B 109.7 . . ?
C7 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
C6 C7 C8 110.54(10) . . ?
C6 C7 H7A 109.5 . . ?
C8 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C7 C8 C3 113.73(9) . . ?
C7 C8 H8A 108.8 . . ?
C3 C8 H8A 108.8 . . ?
C7 C8 H8B 108.8 . . ?
C3 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
O10 C10 N9 121.76(10) . . ?
O10 C10 C11 120.98(10) . . ?
N9 C10 C11 117.25(10) . . ?
C19 C11 C10 126.26(10) . . ?
C19 C11 S12 111.38(8) . . ?
C10 C11 S12 122.32(8) . . ?
C14 C13 S12 112.08(9) . . ?
C14 C13 H13 124.0 . . ?
S12 C13 H13 124.0 . . ?
C13 C14 C19 112.73(10) . . ?
C13 C14 C15 125.26(11) . . ?
C19 C14 C15 122.01(11) . . ?
C14 C15 C16 109.99(10) . . ?
C14 C15 H15A 109.7 . . ?
C16 C15 H15A 109.7 . . ?
C14 C15 H15B 109.7 . . ?
C16 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
C17 C16 C15 109.48(10) . . ?
C17 C16 H16A 109.8 . . ?
C15 C16 H16A 109.8 . . ?
C17 C16 H16B 109.8 . . ?
C15 C16 H16B 109.8 . . ?
H16A C16 H16B 108.2 . . ?
C16 C17 C18 112.23(10) . . ?
C16 C17 H17A 109.2 . . ?
C18 C17 H17A 109.2 . . ?
C16 C17 H17B 109.2 . . ?
C18 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C19 C18 C17 112.77(10) . . ?
C19 C18 H18A 109.0 . . ?
C17 C18 H18A 109.0 . . ?
C19 C18 H18B 109.0 . . ?
C17 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
C11 C19 C14 111.86(10) . . ?
C11 C19 C18 126.23(10) . . ?
C14 C19 C18 121.84(10) . . ?
O1A C2A C3A 107.38(11) . . ?
O1A C2A H2A1 110.2 . . ?
C3A C2A H2A1 110.2 . . ?
O1A C2A H2A2 110.2 . . ?
C3A C2A H2A2 110.2 . . ?
H2A1 C2A H2A2 108.5 . . ?
C2A C3A H3A1 109.5 . . ?
C2A C3A H3A2 109.5 . . ?
H3A1 C3A H3A2 109.5 . . ?
C2A C3A H3A3 109.5 . . ?
H3A1 C3A H3A3 109.5 . . ?
H3A2 C3A H3A3 109.5 . . ?
O1B C2B C3B 107.31(11) . . ?
O1B C2B H2B1 110.3 . . ?
C3B C2B H2B1 110.3 . . ?
O1B C2B H2B2 110.3 . . ?
C3B C2B H2B2 110.3 . . ?
H2B1 C2B H2B2 108.5 . . ?
C2B C3B H3B1 109.5 . . ?
C2B C3B H3B2 109.5 . . ?
H3B1 C3B H3B2 109.5 . . ?
C2B C3B H3B3 109.5 . . ?
H3B1 C3B H3B3 109.5 . . ?
H3B2 C3B H3B3 109.5 . . ?
O4C C4C O5C 124.96(10) . . ?
O4C C4C N4 124.07(10) . . ?
O5C C4C N4 110.96(9) . . ?
O5C C6C C9C 109.84(9) . . ?
O5C C6C C8C 102.28(9) . . ?
C9C C6C C8C 110.49(10) . . ?
O5C C6C C7C 110.07(9) . . ?
C9C C6C C7C 112.93(10) . . ?
C8C C6C C7C 110.71(10) . . ?
C6C C7C H7C1 109.5 . . ?
C6C C7C H7C2 109.5 . . ?
H7C1 C7C H7C2 109.5 . . ?
C6C C7C H7C3 109.5 . . ?
H7C1 C7C H7C3 109.5 . . ?
H7C2 C7C H7C3 109.5 . . ?
C6C C8C H8C1 109.5 . . ?
C6C C8C H8C2 109.5 . . ?
H8C1 C8C H8C2 109.5 . . ?
C6C C8C H8C3 109.5 . . ?
H8C1 C8C H8C3 109.5 . . ?
H8C2 C8C H8C3 109.5 . . ?
C6C C9C H9C1 109.5 . . ?
C6C C9C H9C2 109.5 . . ?
H9C1 C9C H9C2 109.5 . . ?
C6C C9C H9C3 109.5 . . ?
H9C1 C9C H9C3 109.5 . . ?
H9C2 C9C H9C3 109.5 . . ?
H20A O20 H20B 104.2(17) . . ?

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
O1 P1 O1A C2A 72.65(13) . . . . ?
O1B P1 O1A C2A -52.47(13) . . . . ?
C2 P1 O1A C2A -161.16(12) . . . . ?
O1 P1 O1B C2B 21.80(12) . . . . ?
O1A P1 O1B C2B 149.23(10) . . . . ?
C2 P1 O1B C2B -104.49(10) . . . . ?
C10 N9 C2 C3 106.71(11) . . . . ?
C10 N9 C2 P1 -124.93(9) . . . . ?
O1 P1 C2 N9 -64.27(9) . . . . ?
O1A P1 C2 N9 168.14(7) . . . . ?
O1B P1 C2 N9 61.12(8) . . . . ?
O1 P1 C2 C3 60.97(9) . . . . ?
O1A P1 C2 C3 -66.63(9) . . . . ?
O1B P1 C2 C3 -173.64(7) . . . . ?
C4C N4 C3 C8 132.58(11) . . . . ?
C5 N4 C3 C8 -52.37(12) . . . . ?
C4C N4 C3 C2 -104.77(12) . . . . ?
C5 N4 C3 C2 70.28(12) . . . . ?
N9 C2 C3 N4 176.01(9) . . . . ?
P1 C2 C3 N4 52.94(11) . . . . ?
N9 C2 C3 C8 -61.86(11) . . . . ?
P1 C2 C3 C8 175.06(7) . . . . ?
C4C N4 C5 C6 -127.95(11) . . . . ?
C3 N4 C5 C6 56.71(12) . . . . ?
N4 C5 C6 C7 -55.64(13) . . . . ?
C5 C6 C7 C8 54.76(13) . . . . ?
C6 C7 C8 C3 -53.17(13) . . . . ?
N4 C3 C8 C7 49.82(12) . . . . ?
C2 C3 C8 C7 -74.30(12) . . . . ?
C2 N9 C10 O10 1.40(17) . . . . ?
C2 N9 C10 C11 -179.61(9) . . . . ?
O10 C10 C11 C19 -11.30(18) . . . . ?
N9 C10 C11 C19 169.71(11) . . . . ?
O10 C10 C11 S12 166.37(9) . . . . ?
N9 C10 C11 S12 -12.62(15) . . . . ?
C13 S12 C11 C19 -0.27(9) . . . . ?
C13 S12 C11 C10 -178.25(10) . . . . ?
C11 S12 C13 C14 -0.19(10) . . . . ?
S12 C13 C14 C19 0.59(13) . . . . ?
S12 C13 C14 C15 -178.57(9) . . . . ?
C13 C14 C15 C16 154.38(12) . . . . ?
C19 C14 C15 C16 -24.70(15) . . . . ?
C14 C15 C16 C17 54.89(13) . . . . ?
C15 C16 C17 C18 -64.56(13) . . . . ?
C16 C17 C18 C19 39.31(14) . . . . ?
C10 C11 C19 C14 178.52(10) . . . . ?
S12 C11 C19 C14 0.64(12) . . . . ?
C10 C11 C19 C18 -4.28(19) . . . . ?
S12 C11 C19 C18 177.84(9) . . . . ?
C13 C14 C19 C11 -0.79(14) . . . . ?
C15 C14 C19 C11 178.39(10) . . . . ?
C13 C14 C19 C18 -178.13(11) . . . . ?
C15 C14 C19 C18 1.05(17) . . . . ?
C17 C18 C19 C11 175.05(11) . . . . ?
C17 C18 C19 C14 -8.01(16) . . . . ?
P1 O1A C2A C3A 174.85(11) . . . . ?
P1 O1B C2B C3B -146.72(10) . . . . ?
C6C O5C C4C O4C -9.73(16) . . . . ?
C6C O5C C4C N4 171.33(9) . . . . ?
C3 N4 C4C O4C 177.50(10) . . . . ?
C5 N4 C4C O4C 2.54(17) . . . . ?
C3 N4 C4C O5C -3.55(15) . . . . ?
C5 N4 C4C O5C -178.51(9) . . . . ?
C4C O5C C6C C9C -59.59(13) . . . . ?
C4C O5C C6C C8C -176.94(10) . . . . ?
C4C O5C C6C C7C 65.36(13) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N9 H9 O20 0.874(12) 2.120(13) 2.9398(14) 156.0(13) . yes
O20 H20A O1 0.837(14) 2.060(15) 2.8728(12) 163.7(18) 2_665 yes
O20 H20B O1 0.848(14) 2.078(15) 2.8786(13) 157.3(17) . yes

_refine_diff_density_max         0.400
_refine_diff_density_min         -0.368
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_4b-2
_database_code_depnum_ccdc_archive 'CCDC 2203660'
loop_
_audit_author_name
_audit_author_address
'Arto Valkonen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2022-08-26 deposited with the CCDC.	2023-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H33 N2 O6 P S'
_chemical_formula_sum            'C20 H33 N2 O6 P S'
_chemical_formula_weight         460.51

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'
S S 0.1246 0.1234 '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'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   15.5581(5)
_cell_length_b                   16.4388(5)
_cell_length_c                   19.9240(5)
_cell_angle_alpha                94.181(2)
_cell_angle_beta                 98.983(2)
_cell_angle_gamma                90.241(2)
_cell_volume                     5019.2(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    8983
_cell_measurement_theta_min      2.1390
_cell_measurement_theta_max      23.2940

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_F_000             1968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.510
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.350
_exptl_absorpt_coefficient_mu    0.227
_shelx_estimated_absorpt_T_min   0.893
_shelx_estimated_absorpt_T_max   0.925
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.926
_exptl_absorpt_correction_T_max  0.944
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0107
_diffrn_reflns_number            45947
_diffrn_reflns_av_unetI/netI     0.0527
_diffrn_reflns_av_R_equivalents  0.0262
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.807
_diffrn_reflns_theta_max         29.928
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.869
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.869
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.869
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             25262
_reflns_number_gt                12431
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    SHELXL-2018/3
_computing_publication_material  SHELXL-2018/3
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0811P)²+1.2977P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         25262
_refine_ls_number_parameters     1197
_refine_ls_number_restraints     356
_refine_ls_R_factor_all          0.1386
_refine_ls_R_factor_gt           0.0680
_refine_ls_wR_factor_ref         0.2105
_refine_ls_wR_factor_gt          0.1662
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S12 S -0.21729(7) 0.31739(8) 0.03951(6) 0.1219(4) Uani 1 1 d . . . . .
P1 P 0.13952(5) 0.37630(5) 0.24283(4) 0.0737(2) Uani 1 1 d . . . . .
O1 O 0.14177(15) 0.45066(12) 0.28818(10) 0.0844(6) Uani 1 1 d . . . . .
O10 O -0.03012(16) 0.28855(14) 0.07602(15) 0.1127(9) Uani 1 1 d . . . . .
O1A O 0.08520(17) 0.30470(13) 0.26439(12) 0.0926(7) Uani 1 1 d D . . . .
O1B O 0.22835(15) 0.33533(15) 0.23631(12) 0.1003(7) Uani 1 1 d D . . . .
O4C O 0.25841(15) 0.57823(13) 0.18906(13) 0.0952(7) Uani 1 1 d . . . . .
O5C O 0.36376(14) 0.50961(14) 0.14380(14) 0.0972(7) Uani 1 1 d . . . . .
N4 N 0.23164(14) 0.45428(13) 0.13146(11) 0.0636(6) Uani 1 1 d . . . . .
N9 N 0.00231(15) 0.40026(14) 0.14888(13) 0.0702(6) Uani 1 1 d D . . . .
H9 H -0.0166(19) 0.4486(13) 0.1656(15) 0.084 Uiso 1 1 d D U . . .
C2 C 0.09610(17) 0.39005(16) 0.15454(14) 0.0649(7) Uani 1 1 d . . . . .
H2 H 0.107184 0.340660 0.126781 0.078 Uiso 1 1 calc R U . . .
C3 C 0.13786(17) 0.46333(16) 0.12742(14) 0.0633(7) Uani 1 1 d . . . . .
H3 H 0.127758 0.512038 0.156361 0.076 Uiso 1 1 calc R U . . .
C5 C 0.2592(2) 0.39169(17) 0.08308(16) 0.0783(9) Uani 1 1 d . . . . .
H5A H 0.238825 0.338451 0.092398 0.094 Uiso 1 1 calc R U . . .
H5B H 0.322276 0.390978 0.088667 0.094 Uiso 1 1 calc R U . . .
C6 C 0.2229(3) 0.4091(2) 0.01053(18) 0.0964(11) Uani 1 1 d . . . . .
H6A H 0.238461 0.365651 -0.020744 0.116 Uiso 1 1 calc R U . . .
H6B H 0.247789 0.459778 -0.000340 0.116 Uiso 1 1 calc R U . . .
C7 C 0.1243(3) 0.4155(2) 0.00236(17) 0.1015(12) Uani 1 1 d . . . . .
H7A H 0.101999 0.430842 -0.043103 0.122 Uiso 1 1 calc R U . . .
H7B H 0.099108 0.362811 0.007920 0.122 Uiso 1 1 calc R U . . .
C8 C 0.0983(2) 0.4779(2) 0.05425(16) 0.0836(9) Uani 1 1 d . . . . .
H8A H 0.035426 0.477313 0.050500 0.100 Uiso 1 1 calc R U . . .
H8B H 0.116327 0.531586 0.044028 0.100 Uiso 1 1 calc R U . . .
C10 C -0.0534(2) 0.34843(18) 0.10789(17) 0.0771(8) Uani 1 1 d . . . . .
C11 C -0.1465(2) 0.36863(19) 0.10277(16) 0.0736(8) Uani 1 1 d . . . . .
C13 C -0.3032(3) 0.3660(3) 0.0646(2) 0.1263(16) Uani 1 1 d . . . . .
H13 H -0.360483 0.356834 0.043703 0.152 Uiso 1 1 calc R U . . .
C14 C -0.2793(3) 0.4187(3) 0.1177(3) 0.1255(15) Uani 1 1 d . . . . .
H14 H -0.318205 0.451187 0.138099 0.151 Uiso 1 1 calc R U . . .
C15 C -0.1886(2) 0.4205(2) 0.1401(2) 0.0961(11) Uani 1 1 d . . . . .
H15 H -0.161268 0.454199 0.176905 0.115 Uiso 1 1 calc R U . . .
C2A C 0.0357(9) 0.3201(9) 0.3228(6) 0.111(4) Uani 0.5 1 d D U P A 1
H2A H 0.073262 0.348711 0.360742 0.133 Uiso 0.5 1 calc R U P A 1
H2B H -0.013236 0.354888 0.309197 0.133 Uiso 0.5 1 calc R U P A 1
C3A C 0.0030(14) 0.2427(10) 0.3455(13) 0.117(4) Uani 0.5 1 d D U P A 1
H3A H -0.028253 0.254982 0.382780 0.176 Uiso 0.5 1 calc R U P A 1
H3B H -0.035138 0.214733 0.308306 0.176 Uiso 0.5 1 calc R U P A 1
H3C H 0.051304 0.208560 0.359817 0.176 Uiso 0.5 1 calc R U P A 1
C2D C 0.0085(8) 0.3122(9) 0.2925(6) 0.113(4) Uani 0.5 1 d D U P A 2
H2E H -0.041642 0.291963 0.260267 0.135 Uiso 0.5 1 calc R U P A 2
H2F H -0.001094 0.368291 0.307856 0.135 Uiso 0.5 1 calc R U P A 2
C3D C 0.0268(14) 0.2603(11) 0.3502(12) 0.131(5) Uani 0.5 1 d D U P A 2
H3G H -0.022129 0.260444 0.374138 0.197 Uiso 0.5 1 calc R U P A 2
H3H H 0.037226 0.205601 0.333432 0.197 Uiso 0.5 1 calc R U P A 2
H3I H 0.077393 0.281212 0.380575 0.197 Uiso 0.5 1 calc R U P A 2
C2B C 0.2912(12) 0.3013(14) 0.2874(11) 0.122(6) Uani 0.5 1 d D U P B 1
H2C H 0.314955 0.252070 0.268065 0.147 Uiso 0.5 1 calc R U P B 1
H2D H 0.262888 0.286754 0.325044 0.147 Uiso 0.5 1 calc R U P B 1
C3B C 0.3615(11) 0.3600(13) 0.3125(10) 0.139(6) Uani 0.5 1 d D U P B 1
H3D H 0.402786 0.336551 0.346394 0.209 Uiso 0.5 1 calc R U P B 1
H3E H 0.390036 0.373753 0.275331 0.209 Uiso 0.5 1 calc R U P B 1
H3F H 0.338066 0.408373 0.332204 0.209 Uiso 0.5 1 calc R U P B 1
C2E C 0.2869(11) 0.3241(15) 0.2995(11) 0.126(6) Uani 0.5 1 d D U P B 2
H2G H 0.282375 0.268538 0.312158 0.151 Uiso 0.5 1 calc R U P B 2
H2H H 0.272283 0.360974 0.336101 0.151 Uiso 0.5 1 calc R U P B 2
C3E C 0.3749(11) 0.3414(15) 0.2871(10) 0.146(6) Uani 0.5 1 d D U P B 2
H3J H 0.415566 0.334559 0.327734 0.219 Uiso 0.5 1 calc R U P B 2
H3K H 0.388577 0.304437 0.250801 0.219 Uiso 0.5 1 calc R U P B 2
H3L H 0.378533 0.396438 0.274631 0.219 Uiso 0.5 1 calc R U P B 2
C4C C 0.2829(2) 0.51974(18) 0.15776(16) 0.0724(8) Uani 1 1 d . . . . .
C6C C 0.4292(3) 0.5751(2) 0.1602(2) 0.1097(13) Uani 1 1 d . . . . .
C7C C 0.4517(4) 0.5900(4) 0.2363(3) 0.181(3) Uani 1 1 d . . . . .
H7C H 0.494629 0.633035 0.247156 0.271 Uiso 1 1 calc R U . . .
H7D H 0.400363 0.605437 0.255007 0.271 Uiso 1 1 calc R U . . .
H7E H 0.474482 0.541089 0.255359 0.271 Uiso 1 1 calc R U . . .
C8C C 0.5038(3) 0.5384(4) 0.1284(4) 0.199(3) Uani 1 1 d . . . . .
H8C H 0.552068 0.576337 0.135747 0.299 Uiso 1 1 calc R U . . .
H8D H 0.521202 0.488808 0.148869 0.299 Uiso 1 1 calc R U . . .
H8E H 0.485469 0.526928 0.080322 0.299 Uiso 1 1 calc R U . . .
C9C C 0.3972(3) 0.6513(3) 0.1288(2) 0.1371(17) Uani 1 1 d . . . . .
H9A H 0.441070 0.693445 0.140278 0.206 Uiso 1 1 calc R U . . .
H9B H 0.384689 0.641073 0.080232 0.206 Uiso 1 1 calc R U . . .
H9C H 0.345219 0.668509 0.145865 0.206 Uiso 1 1 calc R U . . .
S27 S 0.32961(8) 0.70938(6) 0.44276(5) 0.1083(4) Uani 1 1 d . U . . .
P16 P -0.02743(5) 0.64002(4) 0.23296(4) 0.0661(2) Uani 1 1 d . . . . .
O16 O -0.03349(14) 0.56328(11) 0.19117(9) 0.0761(5) Uani 1 1 d . . . . .
O25 O 0.14680(17) 0.73988(14) 0.39220(12) 0.0982(7) Uani 1 1 d . . . . .
O16A O 0.02499(19) 0.70889(13) 0.20657(11) 0.0977(8) Uani 1 1 d D . . . .
O16B O -0.11532(15) 0.68162(13) 0.24078(10) 0.0866(6) Uani 1 1 d D . . . .
O19C O -0.13387(15) 0.43778(13) 0.32074(13) 0.0959(7) Uani 1 1 d . . . . .
O20C O -0.23839(15) 0.51160(14) 0.36224(12) 0.0926(7) Uani 1 1 d . . . . .
N19 N -0.11165(15) 0.57152(14) 0.35443(12) 0.0663(6) Uani 1 1 d . . . . .
N24 N 0.11461(16) 0.62298(14) 0.32603(11) 0.0639(6) Uani 1 1 d D . . . .
H24 H 0.1344(18) 0.5757(13) 0.3111(14) 0.077 Uiso 1 1 d D U . . .
C17 C 0.02186(18) 0.63395(15) 0.32072(12) 0.0606(7) Uani 1 1 d . . . . .
H17 H 0.012249 0.685901 0.345619 0.073 Uiso 1 1 calc R U . . .
C18 C -0.01737(18) 0.56484(16) 0.35631(13) 0.0613(7) Uani 1 1 d . . . . .
H18 H -0.006572 0.512854 0.331947 0.074 Uiso 1 1 calc R U . . .
C20 C -0.1380(2) 0.64225(19) 0.39570(17) 0.0838(9) Uani 1 1 d . . . . .
H20A H -0.200849 0.641702 0.392950 0.101 Uiso 1 1 calc R U . . .
H20B H -0.121033 0.692192 0.377837 0.101 Uiso 1 1 calc R U . . .
C21 C -0.0958(3) 0.6402(2) 0.46949(17) 0.0987(11) Uani 1 1 d . . . . .
H21A H -0.109486 0.689784 0.494956 0.118 Uiso 1 1 calc R U . . .
H21B H -0.119319 0.594373 0.489133 0.118 Uiso 1 1 calc R U . . .
C22 C 0.0022(3) 0.6327(2) 0.47569(16) 0.0949(11) Uani 1 1 d . . . . .
H22A H 0.026826 0.682648 0.463098 0.114 Uiso 1 1 calc R U . . .
H22B H 0.026569 0.625201 0.522647 0.114 Uiso 1 1 calc R U . . .
C23 C 0.0261(2) 0.56181(19) 0.43043(14) 0.0777(8) Uani 1 1 d . . . . .
H23A H 0.009179 0.511393 0.447578 0.093 Uiso 1 1 calc R U . . .
H23B H 0.088808 0.561652 0.432214 0.093 Uiso 1 1 calc R U . . .
C25 C 0.1702(2) 0.67442(19) 0.36834(15) 0.0733(8) Uani 1 1 d . . . . .
C26 C 0.2595(2) 0.6473(2) 0.38668(15) 0.0787(9) Uani 1 1 d . U . . .
C28 C 0.4086(3) 0.6425(3) 0.44328(19) 0.1125(13) Uani 1 1 d . U . . .
H28 H 0.463959 0.651922 0.468094 0.135 Uiso 1 1 calc R U . . .
C29 C 0.3857(3) 0.5745(3) 0.4051(2) 0.1381(16) Uani 1 1 d . U . . .
H29 H 0.422420 0.530564 0.400735 0.166 Uiso 1 1 calc R U . . .
C30 C 0.2980(2) 0.5764(3) 0.3715(2) 0.1198(14) Uani 1 1 d . U . . .
H30 H 0.270631 0.533918 0.342516 0.144 Uiso 1 1 calc R U . . .
C17A C 0.0609(13) 0.7033(14) 0.1445(8) 0.107(4) Uani 0.5 1 d D U P C 1
H17A H 0.123616 0.699285 0.155184 0.128 Uiso 0.5 1 calc R U P C 1
H17B H 0.038803 0.654054 0.117484 0.128 Uiso 0.5 1 calc R U P C 1
C18A C 0.0406(9) 0.7700(11) 0.1066(9) 0.112(3) Uani 0.5 1 d D U P C 1
H18A H 0.065862 0.763741 0.065616 0.168 Uiso 0.5 1 calc R U P C 1
H18B H -0.021486 0.773665 0.095161 0.168 Uiso 0.5 1 calc R U P C 1
H18C H 0.063303 0.818884 0.132850 0.168 Uiso 0.5 1 calc R U P C 1
C17D C 0.0817(14) 0.6962(16) 0.1593(9) 0.112(4) Uani 0.5 1 d D U P C 2
H17C H 0.140567 0.694124 0.183877 0.135 Uiso 0.5 1 calc R U P C 2
H17D H 0.068215 0.643473 0.134756 0.135 Uiso 0.5 1 calc R U P C 2
C18D C 0.0796(9) 0.7544(12) 0.1126(9) 0.131(4) Uani 0.5 1 d D U P C 2
H18D H 0.120492 0.740872 0.082281 0.197 Uiso 0.5 1 calc R U P C 2
H18E H 0.022111 0.756085 0.086894 0.197 Uiso 0.5 1 calc R U P C 2
H18F H 0.094612 0.806841 0.136117 0.197 Uiso 0.5 1 calc R U P C 2
C17B C -0.1845(8) 0.6968(18) 0.1872(9) 0.114(4) Uani 0.5 1 d D U P D 1
H17E H -0.195759 0.754844 0.189085 0.137 Uiso 0.5 1 calc R U P D 1
H17F H -0.165417 0.681983 0.143876 0.137 Uiso 0.5 1 calc R U P D 1
C18B C -0.2638(8) 0.6541(8) 0.1891(7) 0.138(4) Uani 0.5 1 d D U P D 1
H18G H -0.306589 0.667623 0.151537 0.207 Uiso 0.5 1 calc R U P D 1
H18H H -0.254006 0.596400 0.185851 0.207 Uiso 0.5 1 calc R U P D 1
H18I H -0.284402 0.669388 0.231139 0.207 Uiso 0.5 1 calc R U P D 1
C17E C -0.1858(8) 0.6757(19) 0.1852(8) 0.119(5) Uani 0.5 1 d D U P D 2
H17G H -0.191788 0.620403 0.164177 0.143 Uiso 0.5 1 calc R U P D 2
H17H H -0.176103 0.712284 0.150988 0.143 Uiso 0.5 1 calc R U P D 2
C18E C -0.2621(8) 0.6981(8) 0.2136(6) 0.125(4) Uani 0.5 1 d D U P D 2
H18J H -0.311686 0.695081 0.178117 0.187 Uiso 0.5 1 calc R U P D 2
H18K H -0.270646 0.661397 0.247375 0.187 Uiso 0.5 1 calc R U P D 2
H18L H -0.255046 0.752774 0.234257 0.187 Uiso 0.5 1 calc R U P D 2
C19C C -0.1590(2) 0.5008(2) 0.34422(15) 0.0713(8) Uani 1 1 d . . . . .
C21C C -0.2978(2) 0.4423(3) 0.3639(2) 0.1015(11) Uani 1 1 d . U . . .
C22C C -0.2546(3) 0.3790(3) 0.4079(3) 0.161(2) Uani 1 1 d . U . . .
H22C H -0.294491 0.334403 0.408224 0.241 Uiso 1 1 calc R U . . .
H22D H -0.203971 0.359407 0.390130 0.241 Uiso 1 1 calc R U . . .
H22E H -0.237594 0.402806 0.453555 0.241 Uiso 1 1 calc R U . . .
C23C C -0.3715(3) 0.4838(3) 0.3943(3) 0.1497(19) Uani 1 1 d . U . . .
H23C H -0.415545 0.444010 0.398063 0.224 Uiso 1 1 calc R U . . .
H23D H -0.349380 0.508928 0.438658 0.224 Uiso 1 1 calc R U . . .
H23E H -0.396256 0.524670 0.365325 0.224 Uiso 1 1 calc R U . . .
C24C C -0.3279(3) 0.4072(3) 0.2914(3) 0.1461(18) Uani 1 1 d . U . . .
H24A H -0.366828 0.361819 0.291770 0.219 Uiso 1 1 calc R U . . .
H24B H -0.357584 0.448409 0.265255 0.219 Uiso 1 1 calc R U . . .
H24C H -0.278442 0.389238 0.271285 0.219 Uiso 1 1 calc R U . . .
S42 S 0.64855(8) 0.79025(8) 0.53963(5) 0.1152(4) Uani 1 1 d . . . . .
P31 P 0.38065(5) 0.86900(5) 0.74715(4) 0.0735(2) Uani 1 1 d . . . . .
O31 O 0.39351(15) 0.94265(13) 0.79302(11) 0.0880(6) Uani 1 1 d . . . . .
O40 O 0.47902(14) 0.77239(14) 0.58345(12) 0.0943(7) Uani 1 1 d . . . . .
O31A O 0.44165(16) 0.79787(14) 0.76945(12) 0.0978(7) Uani 1 1 d D . . . .
O31B O 0.28836(16) 0.82857(16) 0.73772(14) 0.1042(8) Uani 1 1 d D . . . .
O34C O 0.23820(13) 1.07263(13) 0.67937(13) 0.0923(7) Uani 1 1 d . . . . .
O35C O 0.12035(12) 0.99779(12) 0.62883(12) 0.0845(6) Uani 1 1 d . . . . .
N34 N 0.25292(15) 0.94871(14) 0.62615(14) 0.0767(7) Uani 1 1 d . . . . .
N39 N 0.48630(14) 0.88648(14) 0.65469(12) 0.0637(6) Uani 1 1 d D . . . .
H39 H 0.5156(17) 0.9292(13) 0.6738(14) 0.076 Uiso 1 1 d D U . . .
C32 C 0.39456(16) 0.88318(16) 0.65996(14) 0.0652(7) Uani 1 1 d . . . . .
H32 H 0.368771 0.835536 0.631337 0.078 Uiso 1 1 calc R U . . .
C33 C 0.34769(17) 0.95957(17) 0.63299(15) 0.0672(7) Uani 1 1 d . . . . .
H33 H 0.364735 1.005373 0.666833 0.081 Uiso 1 1 calc R U . . .
C35 C 0.2159(2) 0.8877(2) 0.5703(2) 0.0996(12) Uani 1 1 d . U . . .
H35A H 0.153128 0.884884 0.567607 0.119 Uiso 1 1 calc R U . . .
H35B H 0.238873 0.834338 0.579848 0.119 Uiso 1 1 calc R U . . .
C36 C 0.2385(3) 0.9111(3) 0.5027(2) 0.1180(14) Uani 1 1 d . U . . .
H36A H 0.218112 0.868432 0.467457 0.142 Uiso 1 1 calc R U . . .
H36B H 0.209038 0.960985 0.490325 0.142 Uiso 1 1 calc R U . . .
C37 C 0.3350(3) 0.9233(3) 0.5065(2) 0.1122(13) Uani 1 1 d . U . . .
H37A H 0.346986 0.943461 0.464267 0.135 Uiso 1 1 calc R U . . .
H37B H 0.363806 0.871531 0.512134 0.135 Uiso 1 1 calc R U . . .
C38 C 0.3703(2) 0.9832(2) 0.56522(17) 0.0888(10) Uani 1 1 d . . . . .
H38A H 0.347116 1.036731 0.556224 0.107 Uiso 1 1 calc R U . . .
H38B H 0.433106 0.986907 0.568569 0.107 Uiso 1 1 calc R U . . .
C40 C 0.52024(19) 0.83226(18) 0.61313(14) 0.0685(7) Uani 1 1 d . . . . .
C41 C 0.61021(19) 0.84755(19) 0.60315(14) 0.0688(8) Uani 1 1 d . . . . .
C43 C 0.7456(3) 0.8391(3) 0.5563(2) 0.1179(15) Uani 1 1 d . . . . .
H43 H 0.791139 0.827627 0.532166 0.142 Uiso 1 1 calc R U . . .
C44 C 0.7501(3) 0.8960(3) 0.6079(2) 0.1097(12) Uani 1 1 d . . . . .
H44 H 0.799053 0.928637 0.623793 0.132 Uiso 1 1 calc R U . . .
C45 C 0.6723(2) 0.9009(2) 0.63550(18) 0.0858(9) Uani 1 1 d . . . . .
H45 H 0.664289 0.937005 0.672093 0.103 Uiso 1 1 calc R U . . .
C32A C 0.5001(12) 0.8001(13) 0.8348(8) 0.145(5) Uani 0.5 1 d D U P E 1
H32A H 0.559250 0.808353 0.826491 0.174 Uiso 0.5 1 calc R U P E 1
H32B H 0.485671 0.846783 0.863304 0.174 Uiso 0.5 1 calc R U P E 1
C33A C 0.4976(10) 0.7324(9) 0.8694(9) 0.151(4) Uani 0.5 1 d D U P E 1
H33A H 0.537642 0.739046 0.911339 0.226 Uiso 0.5 1 calc R U P E 1
H33B H 0.439753 0.724378 0.879189 0.226 Uiso 0.5 1 calc R U P E 1
H33C H 0.513473 0.685874 0.842306 0.226 Uiso 0.5 1 calc R U P E 1
C32D C 0.5199(11) 0.8098(14) 0.8138(9) 0.142(5) Uani 0.5 1 d D U P E 2
H32C H 0.567293 0.802377 0.787642 0.171 Uiso 0.5 1 calc R U P E 2
H32D H 0.522886 0.865804 0.833047 0.171 Uiso 0.5 1 calc R U P E 2
C33D C 0.5326(10) 0.7599(10) 0.8656(9) 0.166(5) Uani 0.5 1 d D U P E 2
H33D H 0.587898 0.772550 0.893317 0.250 Uiso 0.5 1 calc R U P E 2
H33E H 0.487157 0.767754 0.892896 0.250 Uiso 0.5 1 calc R U P E 2
H33F H 0.531664 0.704184 0.847389 0.250 Uiso 0.5 1 calc R U P E 2
C32B C 0.2359(10) 0.7973(12) 0.7883(9) 0.151(5) Uani 0.5 1 d D U P F 1
H32E H 0.203121 0.748349 0.769539 0.181 Uiso 0.5 1 calc R U P F 1
H32F H 0.273133 0.785671 0.830153 0.181 Uiso 0.5 1 calc R U P F 1
C33B C 0.1818(9) 0.8603(8) 0.7992(11) 0.162(5) Uani 0.5 1 d D U P F 1
H33G H 0.145211 0.845992 0.831289 0.243 Uiso 0.5 1 calc R U P F 1
H33H H 0.215825 0.908089 0.817144 0.243 Uiso 0.5 1 calc R U P F 1
H33I H 0.146365 0.871062 0.757009 0.243 Uiso 0.5 1 calc R U P F 1
C32E C 0.2499(9) 0.8257(13) 0.8011(8) 0.150(5) Uani 0.5 1 d D U P F 2
H32G H 0.273652 0.779005 0.824371 0.180 Uiso 0.5 1 calc R U P F 2
H32H H 0.269481 0.874080 0.830379 0.180 Uiso 0.5 1 calc R U P F 2
C33E C 0.1627(8) 0.8210(10) 0.7953(11) 0.161(5) Uani 0.5 1 d D U P F 2
H33J H 0.146367 0.819518 0.839675 0.241 Uiso 0.5 1 calc R U P F 2
H33K H 0.137628 0.867740 0.773964 0.241 Uiso 0.5 1 calc R U P F 2
H33L H 0.141816 0.772269 0.767931 0.241 Uiso 0.5 1 calc R U P F 2
C34C C 0.20668(18) 1.01212(18) 0.64751(17) 0.0718(8) Uani 1 1 d . . . . .
C36C C 0.05677(19) 1.0620(2) 0.63638(18) 0.0817(9) Uani 1 1 d . U . . .
C37C C 0.0744(3) 1.1299(2) 0.5929(3) 0.1264(15) Uani 1 1 d . U . . .
H37C H 0.033310 1.172581 0.597202 0.190 Uiso 1 1 calc R U . . .
H37D H 0.132363 1.151133 0.607792 0.190 Uiso 1 1 calc R U . . .
H37E H 0.068798 1.109006 0.546133 0.190 Uiso 1 1 calc R U . . .
C38C C -0.0277(2) 1.0179(2) 0.6081(2) 0.1065(12) Uani 1 1 d . U . . .
H38C H -0.075202 1.054501 0.610378 0.160 Uiso 1 1 calc R U . . .
H38D H -0.026886 0.998738 0.561510 0.160 Uiso 1 1 calc R U . . .
H38E H -0.034732 0.972313 0.634367 0.160 Uiso 1 1 calc R U . . .
C39C C 0.0593(3) 1.0911(3) 0.7101(2) 0.1395(18) Uani 1 1 d . U . . .
H39A H 0.017120 1.133040 0.713603 0.209 Uiso 1 1 calc R U . . .
H39B H 0.046110 1.046307 0.735300 0.209 Uiso 1 1 calc R U . . .
H39C H 0.116300 1.112600 0.728409 0.209 Uiso 1 1 calc R U . . .
P46 P 0.56868(6) 1.11646(5) 0.76172(4) 0.0702(2) Uani 1 1 d . . . . .
S57 S 0.29060(7) 1.18536(8) 0.96251(5) 0.1122(4) Uani 1 1 d . U . . .
O46 O 0.55358(15) 1.04300(12) 0.71609(11) 0.0851(6) Uani 1 1 d . . . . .
O55 O 0.46635(17) 1.20680(14) 0.92948(14) 0.1039(8) Uani 1 1 d . . . . .
O46A O 0.50817(17) 1.18898(13) 0.73991(12) 0.0948(7) Uani 1 1 d D . . . .
O46B O 0.66121(15) 1.15623(14) 0.77096(11) 0.0922(7) Uani 1 1 d D . . . .
O49C O 0.70720(15) 0.91844(13) 0.81824(13) 0.0932(7) Uani 1 1 d . . . . .
O50C O 0.82835(14) 0.98876(12) 0.86801(12) 0.0857(6) Uani 1 1 d . . . . .
N49 N 0.69929(14) 1.03938(12) 0.87888(12) 0.0622(6) Uani 1 1 d . . . . .
N54 N 0.46382(16) 1.09692(14) 0.85373(12) 0.0672(6) Uani 1 1 d D . . . .
H54 H 0.4342(17) 1.0535(14) 0.8305(14) 0.081 Uiso 1 1 d D U . . .
C47 C 0.55586(18) 1.10365(16) 0.84950(14) 0.0624(7) Uani 1 1 d . . . . .
H47 H 0.579167 1.152825 0.877258 0.075 Uiso 1 1 calc R U . . .
C48 C 0.60576(18) 1.03001(16) 0.87832(14) 0.0637(7) Uani 1 1 d . . . . .
H48 H 0.585714 0.981676 0.848103 0.076 Uiso 1 1 calc R U . . .
C50 C 0.7428(2) 1.10229(17) 0.92935(16) 0.0756(8) Uani 1 1 d . . . . .
H50A H 0.719888 1.155447 0.918767 0.091 Uiso 1 1 calc R U . . .
H50B H 0.804695 1.103225 0.927433 0.091 Uiso 1 1 calc R U . . .
C51 C 0.7281(3) 1.0846(2) 1.00050(17) 0.0987(11) Uani 1 1 d . . . . .
H51A H 0.756742 1.034365 1.012980 0.118 Uiso 1 1 calc R U . . .
H51B H 0.753487 1.128363 1.032897 0.118 Uiso 1 1 calc R U . . .
C52 C 0.6325(3) 1.0767(3) 1.00366(18) 0.1035(12) Uani 1 1 d . . . . .
H52A H 0.605174 1.129141 0.997153 0.124 Uiso 1 1 calc R U . . .
H52B H 0.624636 1.060773 1.048256 0.124 Uiso 1 1 calc R U . . .
C53 C 0.5892(2) 1.0141(2) 0.94951(17) 0.0877(10) Uani 1 1 d . . . . .
H53A H 0.526964 1.013903 0.950070 0.105 Uiso 1 1 calc R U . . .
H53B H 0.610525 0.960460 0.960306 0.105 Uiso 1 1 calc R U . . .
C55 C 0.4263(2) 1.14910(18) 0.89520(16) 0.0750(8) Uani 1 1 d . . . . .
C56 C 0.3339(2) 1.1339(2) 0.89854(16) 0.0756(8) Uani 1 1 d . U . . .
C58 C 0.1914(3) 1.1420(3) 0.9347(2) 0.1213(14) Uani 1 1 d . U . . .
H58 H 0.142675 1.152862 0.955384 0.146 Uiso 1 1 calc R U . . .
C59 C 0.1912(3) 1.0906(3) 0.8798(2) 0.1124(12) Uani 1 1 d . U . . .
H59 H 0.142183 1.061340 0.858055 0.135 Uiso 1 1 calc R U . . .
C60 C 0.2736(2) 1.0852(2) 0.85811(18) 0.0883(9) Uani 1 1 d . U . . .
H60 H 0.284899 1.052227 0.820645 0.106 Uiso 1 1 calc R U . . .
C47A C 0.4213(5) 1.1810(5) 0.7097(4) 0.093(2) Uiso 0.5 1 d D U P G 1
H47A H 0.382885 1.208165 0.737780 0.112 Uiso 0.5 1 calc R U P G 1
H47B H 0.403480 1.124209 0.699711 0.112 Uiso 0.5 1 calc R U P G 1
C48A C 0.4244(10) 1.2234(9) 0.6457(6) 0.167(5) Uiso 0.5 1 d D U P G 1
H48A H 0.367388 1.222559 0.618960 0.251 Uiso 0.5 1 calc R U P G 1
H48B H 0.443729 1.278869 0.657410 0.251 Uiso 0.5 1 calc R U P G 1
H48C H 0.464109 1.195789 0.619738 0.251 Uiso 0.5 1 calc R U P G 1
C47D C 0.4458(8) 1.1801(7) 0.6762(6) 0.151(4) Uiso 0.5 1 d D U P G 2
H47C H 0.479003 1.171395 0.639033 0.181 Uiso 0.5 1 calc R U P G 2
H47D H 0.411779 1.130741 0.677106 0.181 Uiso 0.5 1 calc R U P G 2
C48D C 0.3856(6) 1.2449(5) 0.6596(5) 0.112(3) Uiso 0.5 1 d D U P G 2
H48D H 0.349399 1.230231 0.616766 0.167 Uiso 0.5 1 calc R U P G 2
H48E H 0.349908 1.253329 0.694571 0.167 Uiso 0.5 1 calc R U P G 2
H48F H 0.417489 1.294199 0.656295 0.167 Uiso 0.5 1 calc R U P G 2
C47B C 0.7033(5) 1.1556(6) 0.7069(4) 0.096(3) Uiso 0.5 1 d D U P H 1
H47E H 0.662552 1.130560 0.669155 0.116 Uiso 0.5 1 calc R U P H 1
H47F H 0.712466 1.211720 0.697227 0.116 Uiso 0.5 1 calc R U P H 1
C48B C 0.7795(7) 1.1168(7) 0.7087(7) 0.112(3) Uiso 0.5 1 d D U P H 1
H48G H 0.800077 1.120188 0.666011 0.169 Uiso 0.5 1 calc R U P H 1
H48H H 0.821390 1.142039 0.744803 0.169 Uiso 0.5 1 calc R U P H 1
H48I H 0.771325 1.060632 0.716646 0.169 Uiso 0.5 1 calc R U P H 1
C47E C 0.7057(5) 1.1880(5) 0.7221(4) 0.0780(19) Uiso 0.5 1 d D U P H 2
H47G H 0.668617 1.184923 0.678082 0.094 Uiso 0.5 1 calc R U P H 2
H47H H 0.721521 1.244704 0.735151 0.094 Uiso 0.5 1 calc R U P H 2
C48E C 0.7801(8) 1.1427(8) 0.7181(9) 0.147(5) Uiso 0.5 1 d D U P H 2
H48J H 0.811066 1.163723 0.684935 0.221 Uiso 0.5 1 calc R U P H 2
H48K H 0.816631 1.146264 0.761792 0.221 Uiso 0.5 1 calc R U P H 2
H48L H 0.763904 1.086683 0.704913 0.221 Uiso 0.5 1 calc R U P H 2
C49C C 0.7420(2) 0.97693(17) 0.85267(15) 0.0669(7) Uani 1 1 d . . . . .
C51C C 0.8896(2) 0.9247(2) 0.85555(19) 0.0888(10) Uani 1 1 d . . . . .
C52C C 0.8874(3) 0.9083(3) 0.7799(2) 0.1433(18) Uani 1 1 d . . . . .
H52C H 0.927763 0.866052 0.771612 0.215 Uiso 1 1 calc R U . . .
H52D H 0.829804 0.891185 0.758902 0.215 Uiso 1 1 calc R U . . .
H52E H 0.903409 0.957152 0.760936 0.215 Uiso 1 1 calc R U . . .
C53C C 0.9753(3) 0.9627(3) 0.8885(3) 0.166(2) Uani 1 1 d . . . . .
H53C H 1.021222 0.924989 0.883260 0.250 Uiso 1 1 calc R U . . .
H53D H 0.985415 1.011606 0.867202 0.250 Uiso 1 1 calc R U . . .
H53E H 0.974140 0.975666 0.936113 0.250 Uiso 1 1 calc R U . . .
C54C C 0.8683(3) 0.8488(3) 0.8866(3) 0.1478(19) Uani 1 1 d . . . . .
H54A H 0.909275 0.807396 0.877808 0.222 Uiso 1 1 calc R U . . .
H54B H 0.871259 0.859915 0.934842 0.222 Uiso 1 1 calc R U . . .
H54C H 0.810603 0.830252 0.866988 0.222 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S12 C13 1.683(5) . ?
S12 C11 1.708(3) . ?
P1 O1 1.463(2) . ?
P1 O1B 1.559(2) . ?
P1 O1A 1.569(2) . ?
P1 C2 1.814(3) . ?
O10 C10 1.219(4) . ?
O1A C2D 1.398(11) . ?
O1A C2A 1.501(10) . ?
O1B C2B 1.444(11) . ?
O1B C2E 1.458(12) . ?
O4C C4C 1.203(3) . ?
O5C C4C 1.339(4) . ?
O5C C6C 1.462(4) . ?
N4 C4C 1.359(3) . ?
N4 C3 1.458(3) . ?
N4 C5 1.470(3) . ?
N9 C10 1.347(3) . ?
N9 C2 1.457(3) . ?
C2 C3 1.537(4) . ?
C3 C8 1.527(4) . ?
C5 C6 1.516(5) . ?
C6 C7 1.521(5) . ?
C7 C8 1.505(5) . ?
C10 C11 1.476(4) . ?
C11 C15 1.333(5) . ?
C13 C14 1.322(6) . ?
C14 C15 1.412(5) . ?
C2A C3A 1.494(14) . ?
C2D C3D 1.474(15) . ?
C2B C3B 1.459(19) . ?
C2E C3E 1.459(19) . ?
C6C C9C 1.493(6) . ?
C6C C7C 1.503(6) . ?
C6C C8C 1.515(6) . ?
S27 C28 1.651(5) . ?
S27 C26 1.710(3) . ?
P16 O16 1.4543(19) . ?
P16 O16B 1.556(2) . ?
P16 O16A 1.561(2) . ?
P16 C17 1.806(3) . ?
O25 C25 1.224(4) . ?
O16A C17D 1.393(11) . ?
O16A C17A 1.431(10) . ?
O16B C17E 1.429(12) . ?
O16B C17B 1.430(11) . ?
O19C C19C 1.197(3) . ?
O20C C19C 1.349(4) . ?
O20C C21C 1.470(4) . ?
N19 C19C 1.359(4) . ?
N19 C18 1.466(3) . ?
N19 C20 1.472(3) . ?
N24 C25 1.355(3) . ?
N24 C17 1.443(4) . ?
C17 C18 1.553(3) . ?
C18 C23 1.530(4) . ?
C20 C21 1.517(5) . ?
C21 C22 1.517(5) . ?
C22 C23 1.505(4) . ?
C25 C26 1.461(5) . ?
C26 C30 1.349(5) . ?
C28 C29 1.321(5) . ?
C29 C30 1.424(5) . ?
C17A C18A 1.386(11) . ?
C17D C18D 1.380(12) . ?
C17B C18B 1.425(17) . ?
C17E C18E 1.430(17) . ?
C21C C22C 1.503(6) . ?
C21C C24C 1.517(6) . ?
C21C C23C 1.521(6) . ?
S42 C43 1.682(5) . ?
S42 C41 1.706(3) . ?
P31 O31 1.456(2) . ?
P31 O31A 1.555(2) . ?
P31 O31B 1.558(2) . ?
P31 C32 1.815(3) . ?
O40 C40 1.233(3) . ?
O31A C32D 1.392(12) . ?
O31A C32A 1.465(11) . ?
O31B C32E 1.484(12) . ?
O31B C32B 1.508(12) . ?
O34C C34C 1.200(3) . ?
O35C C34C 1.352(3) . ?
O35C C36C 1.465(3) . ?
N34 C34C 1.350(3) . ?
N34 C33 1.468(3) . ?
N34 C35 1.486(4) . ?
N39 C40 1.339(3) . ?
N39 C32 1.449(3) . ?
C32 C33 1.543(4) . ?
C33 C38 1.524(4) . ?
C35 C36 1.519(6) . ?
C36 C37 1.503(5) . ?
C37 C38 1.506(5) . ?
C40 C41 1.467(4) . ?
C41 C45 1.354(4) . ?
C43 C44 1.330(5) . ?
C44 C45 1.407(5) . ?
C32A C33A 1.355(13) . ?
C32D C33D 1.356(13) . ?
C32B C33B 1.363(17) . ?
C32E C33E 1.345(16) . ?
C36C C39C 1.506(5) . ?
C36C C38C 1.507(4) . ?
C36C C37C 1.511(5) . ?
P46 O46 1.453(2) . ?
P46 O46B 1.557(2) . ?
P46 O46A 1.566(2) . ?
P46 C47 1.818(3) . ?
S57 C58 1.691(5) . ?
S57 C56 1.706(3) . ?
O55 C55 1.234(4) . ?
O46A C47A 1.393(7) . ?
O46A C47D 1.470(10) . ?
O46B C47E 1.407(7) . ?
O46B C47B 1.523(8) . ?
O49C C49C 1.213(3) . ?
O50C C49C 1.340(3) . ?
O50C C51C 1.457(4) . ?
N49 C49C 1.344(3) . ?
N49 C48 1.461(3) . ?
N49 C50 1.473(3) . ?
N54 C55 1.345(4) . ?
N54 C47 1.452(3) . ?
C47 C48 1.539(4) . ?
C48 C53 1.521(4) . ?
C50 C51 1.519(4) . ?
C51 C52 1.504(5) . ?
C52 C53 1.511(5) . ?
C55 C56 1.472(4) . ?
C56 C60 1.354(5) . ?
C58 C59 1.332(6) . ?
C59 C60 1.416(5) . ?
C47A C48A 1.504(11) . ?
C47D C48D 1.444(11) . ?
C47B C48B 1.345(10) . ?
C47E C48E 1.387(11) . ?
C51C C54C 1.489(5) . ?
C51C C53C 1.504(5) . ?
C51C C52C 1.507(5) . ?

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
C13 S12 C11 91.9(2) . . ?
O1 P1 O1B 117.05(14) . . ?
O1 P1 O1A 113.61(14) . . ?
O1B P1 O1A 102.42(14) . . ?
O1 P1 C2 114.17(12) . . ?
O1B P1 C2 101.82(13) . . ?
O1A P1 C2 106.28(13) . . ?
C2D O1A P1 126.3(7) . . ?
C2A O1A P1 119.1(6) . . ?
C2B O1B P1 130.0(12) . . ?
C2E O1B P1 117.0(12) . . ?
C4C O5C C6C 121.1(3) . . ?
C4C N4 C3 117.3(2) . . ?
C4C N4 C5 122.3(3) . . ?
C3 N4 C5 115.4(2) . . ?
C10 N9 C2 121.0(2) . . ?
N9 C2 C3 110.2(2) . . ?
N9 C2 P1 108.4(2) . . ?
C3 C2 P1 112.60(18) . . ?
N4 C3 C8 109.1(2) . . ?
N4 C3 C2 111.5(2) . . ?
C8 C3 C2 112.9(2) . . ?
N4 C5 C6 110.4(2) . . ?
C5 C6 C7 110.0(3) . . ?
C8 C7 C6 110.7(3) . . ?
C7 C8 C3 113.4(3) . . ?
O10 C10 N9 123.3(3) . . ?
O10 C10 C11 120.8(3) . . ?
N9 C10 C11 115.8(3) . . ?
C15 C11 C10 131.7(3) . . ?
C15 C11 S12 110.8(3) . . ?
C10 C11 S12 117.5(3) . . ?
C14 C13 S12 111.8(3) . . ?
C13 C14 C15 113.0(4) . . ?
C11 C15 C14 112.5(4) . . ?
C3A C2A O1A 111.9(16) . . ?
O1A C2D C3D 101.4(13) . . ?
O1B C2B C3B 110.4(17) . . ?
O1B C2E C3E 107.0(18) . . ?
O4C C4C O5C 125.2(3) . . ?
O4C C4C N4 124.4(3) . . ?
O5C C4C N4 110.3(3) . . ?
O5C C6C C9C 110.9(3) . . ?
O5C C6C C7C 109.4(4) . . ?
C9C C6C C7C 110.7(4) . . ?
O5C C6C C8C 101.1(3) . . ?
C9C C6C C8C 112.1(5) . . ?
C7C C6C C8C 112.3(5) . . ?
C28 S27 C26 92.09(19) . . ?
O16 P16 O16B 115.94(13) . . ?
O16 P16 O16A 114.57(13) . . ?
O16B P16 O16A 102.79(14) . . ?
O16 P16 C17 115.19(12) . . ?
O16B P16 C17 101.88(12) . . ?
O16A P16 C17 104.76(13) . . ?
C17D O16A P16 124.7(11) . . ?
C17A O16A P16 125.6(10) . . ?
C17E O16B P16 119.9(10) . . ?
C17B O16B P16 126.7(10) . . ?
C19C O20C C21C 121.4(3) . . ?
C19C N19 C18 116.9(2) . . ?
C19C N19 C20 121.6(3) . . ?
C18 N19 C20 114.3(2) . . ?
C25 N24 C17 120.1(3) . . ?
N24 C17 C18 108.9(2) . . ?
N24 C17 P16 110.85(18) . . ?
C18 C17 P16 113.53(18) . . ?
N19 C18 C23 108.8(2) . . ?
N19 C18 C17 112.9(2) . . ?
C23 C18 C17 111.8(2) . . ?
N19 C20 C21 110.6(3) . . ?
C22 C21 C20 111.4(3) . . ?
C23 C22 C21 111.0(3) . . ?
C22 C23 C18 112.6(3) . . ?
O25 C25 N24 122.1(3) . . ?
O25 C25 C26 120.7(3) . . ?
N24 C25 C26 117.1(3) . . ?
C30 C26 C25 131.4(3) . . ?
C30 C26 S27 110.5(3) . . ?
C25 C26 S27 117.9(3) . . ?
C29 C28 S27 113.6(3) . . ?
C28 C29 C30 111.9(4) . . ?
C26 C30 C29 111.9(4) . . ?
C18A C17A O16A 112.3(14) . . ?
C18D C17D O16A 115.2(15) . . ?
C18B C17B O16B 114.8(15) . . ?
O16B C17E C18E 106.1(14) . . ?
O19C C19C O20C 124.7(3) . . ?
O19C C19C N19 124.2(3) . . ?
O20C C19C N19 111.1(3) . . ?
O20C C21C C22C 110.9(3) . . ?
O20C C21C C24C 108.7(3) . . ?
C22C C21C C24C 111.6(4) . . ?
O20C C21C C23C 101.4(3) . . ?
C22C C21C C23C 112.1(4) . . ?
C24C C21C C23C 111.6(4) . . ?
C43 S42 C41 91.80(19) . . ?
O31 P31 O31A 114.36(14) . . ?
O31 P31 O31B 115.70(15) . . ?
O31A P31 O31B 102.89(15) . . ?
O31 P31 C32 114.64(13) . . ?
O31A P31 C32 105.45(13) . . ?
O31B P31 C32 102.28(14) . . ?
C32D O31A P31 123.0(10) . . ?
C32A O31A P31 123.5(10) . . ?
C32E O31B P31 115.0(8) . . ?
C32B O31B P31 131.7(8) . . ?
C34C O35C C36C 121.5(2) . . ?
C34C N34 C33 117.7(2) . . ?
C34C N34 C35 122.4(2) . . ?
C33 N34 C35 113.8(2) . . ?
C40 N39 C32 120.6(2) . . ?
N39 C32 C33 111.1(2) . . ?
N39 C32 P31 110.06(18) . . ?
C33 C32 P31 112.16(19) . . ?
N34 C33 C38 108.7(2) . . ?
N34 C33 C32 110.6(2) . . ?
C38 C33 C32 114.4(2) . . ?
N34 C35 C36 110.4(3) . . ?
C37 C36 C35 111.3(3) . . ?
C36 C37 C38 110.8(3) . . ?
C37 C38 C33 112.8(3) . . ?
O40 C40 N39 122.9(3) . . ?
O40 C40 C41 120.4(3) . . ?
N39 C40 C41 116.7(3) . . ?
C45 C41 C40 131.9(3) . . ?
C45 C41 S42 110.5(2) . . ?
C40 C41 S42 117.6(2) . . ?
C44 C43 S42 112.7(3) . . ?
C43 C44 C45 112.1(4) . . ?
C41 C45 C44 112.8(3) . . ?
C33A C32A O31A 115.0(14) . . ?
C33D C32D O31A 115.4(14) . . ?
C33B C32B O31B 103.2(14) . . ?
C33E C32E O31B 117.8(17) . . ?
O34C C34C N34 124.4(3) . . ?
O34C C34C O35C 124.7(3) . . ?
N34 C34C O35C 110.9(2) . . ?
O35C C36C C39C 111.2(3) . . ?
O35C C36C C38C 101.7(3) . . ?
C39C C36C C38C 111.2(3) . . ?
O35C C36C C37C 108.2(3) . . ?
C39C C36C C37C 112.6(4) . . ?
C38C C36C C37C 111.3(3) . . ?
O46 P46 O46B 116.69(14) . . ?
O46 P46 O46A 114.28(14) . . ?
O46B P46 O46A 102.58(14) . . ?
O46 P46 C47 114.95(13) . . ?
O46B P46 C47 101.59(13) . . ?
O46A P46 C47 105.02(13) . . ?
C58 S57 C56 91.6(2) . . ?
C47A O46A P46 125.0(4) . . ?
C47D O46A P46 119.9(5) . . ?
C47E O46B P46 129.4(4) . . ?
C47B O46B P46 115.7(4) . . ?
C49C O50C C51C 122.1(2) . . ?
C49C N49 C48 118.4(2) . . ?
C49C N49 C50 122.8(2) . . ?
C48 N49 C50 114.9(2) . . ?
C55 N54 C47 121.1(2) . . ?
N54 C47 C48 111.1(2) . . ?
N54 C47 P46 109.10(19) . . ?
C48 C47 P46 112.55(18) . . ?
N49 C48 C53 109.3(2) . . ?
N49 C48 C47 111.4(2) . . ?
C53 C48 C47 113.1(2) . . ?
N49 C50 C51 110.2(2) . . ?
C52 C51 C50 110.8(3) . . ?
C51 C52 C53 110.9(3) . . ?
C52 C53 C48 113.0(3) . . ?
O55 C55 N54 122.7(3) . . ?
O55 C55 C56 120.7(3) . . ?
N54 C55 C56 116.6(3) . . ?
C60 C56 C55 131.0(3) . . ?
C60 C56 S57 111.5(3) . . ?
C55 C56 S57 117.5(3) . . ?
C59 C58 S57 112.2(3) . . ?
C58 C59 C60 112.9(4) . . ?
C56 C60 C59 111.8(4) . . ?
O46A C47A C48A 100.2(8) . . ?
C48D C47D O46A 119.3(8) . . ?
C48B C47B O46B 116.4(8) . . ?
C48E C47E O46B 108.6(9) . . ?
O49C C49C O50C 124.4(3) . . ?
O49C C49C N49 124.5(3) . . ?
O50C C49C N49 111.1(2) . . ?
O50C C51C C54C 110.7(3) . . ?
O50C C51C C53C 102.4(3) . . ?
C54C C51C C53C 112.9(4) . . ?
O50C C51C C52C 109.4(3) . . ?
C54C C51C C52C 110.5(4) . . ?
C53C C51C C52C 110.7(4) . . ?

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
O1 P1 O1A C2D 36.6(7) . . . . ?
O1B P1 O1A C2D 163.8(7) . . . . ?
C2 P1 O1A C2D -89.7(7) . . . . ?
O1 P1 O1A C2A 5.5(7) . . . . ?
O1B P1 O1A C2A 132.7(7) . . . . ?
C2 P1 O1A C2A -120.9(7) . . . . ?
O1 P1 O1B C2B 61.6(10) . . . . ?
O1A P1 O1B C2B -63.4(10) . . . . ?
C2 P1 O1B C2B -173.2(10) . . . . ?
O1 P1 O1B C2E 47.5(9) . . . . ?
O1A P1 O1B C2E -77.4(9) . . . . ?
C2 P1 O1B C2E 172.8(9) . . . . ?
C10 N9 C2 C3 115.8(3) . . . . ?
C10 N9 C2 P1 -120.6(3) . . . . ?
O1 P1 C2 N9 -73.0(2) . . . . ?
O1B P1 C2 N9 159.94(18) . . . . ?
O1A P1 C2 N9 53.1(2) . . . . ?
O1 P1 C2 C3 49.2(2) . . . . ?
O1B P1 C2 C3 -77.9(2) . . . . ?
O1A P1 C2 C3 175.26(19) . . . . ?
C4C N4 C3 C8 101.4(3) . . . . ?
C5 N4 C3 C8 -54.3(3) . . . . ?
C4C N4 C3 C2 -133.2(3) . . . . ?
C5 N4 C3 C2 71.1(3) . . . . ?
N9 C2 C3 N4 -179.1(2) . . . . ?
P1 C2 C3 N4 59.7(3) . . . . ?
N9 C2 C3 C8 -55.9(3) . . . . ?
P1 C2 C3 C8 -177.1(2) . . . . ?
C4C N4 C5 C6 -96.5(3) . . . . ?
C3 N4 C5 C6 57.8(3) . . . . ?
N4 C5 C6 C7 -55.8(4) . . . . ?
C5 C6 C7 C8 54.7(4) . . . . ?
C6 C7 C8 C3 -53.7(4) . . . . ?
N4 C3 C8 C7 51.8(4) . . . . ?
C2 C3 C8 C7 -72.7(4) . . . . ?
C2 N9 C10 O10 3.6(5) . . . . ?
C2 N9 C10 C11 -175.8(3) . . . . ?
O10 C10 C11 C15 166.7(4) . . . . ?
N9 C10 C11 C15 -13.9(5) . . . . ?
O10 C10 C11 S12 -12.0(4) . . . . ?
N9 C10 C11 S12 167.4(2) . . . . ?
C13 S12 C11 C15 -0.5(3) . . . . ?
C13 S12 C11 C10 178.5(3) . . . . ?
C11 S12 C13 C14 0.5(4) . . . . ?
S12 C13 C14 C15 -0.5(6) . . . . ?
C10 C11 C15 C14 -178.5(4) . . . . ?
S12 C11 C15 C14 0.3(4) . . . . ?
C13 C14 C15 C11 0.1(6) . . . . ?
P1 O1A C2A C3A -168.4(12) . . . . ?
P1 O1A C2D C3D -132.8(12) . . . . ?
P1 O1B C2B C3B -98.2(19) . . . . ?
P1 O1B C2E C3E -141(2) . . . . ?
C6C O5C C4C O4C -6.5(5) . . . . ?
C6C O5C C4C N4 173.5(3) . . . . ?
C3 N4 C4C O4C 14.4(4) . . . . ?
C5 N4 C4C O4C 168.3(3) . . . . ?
C3 N4 C4C O5C -165.6(2) . . . . ?
C5 N4 C4C O5C -11.7(4) . . . . ?
C4C O5C C6C C9C -55.0(5) . . . . ?
C4C O5C C6C C7C 67.3(5) . . . . ?
C4C O5C C6C C8C -174.0(4) . . . . ?
O16 P16 O16A C17D -17.0(11) . . . . ?
O16B P16 O16A C17D -143.7(11) . . . . ?
C17 P16 O16A C17D 110.2(11) . . . . ?
O16 P16 O16A C17A 4.2(10) . . . . ?
O16B P16 O16A C17A -122.5(9) . . . . ?
C17 P16 O16A C17A 131.3(9) . . . . ?
O16 P16 O16B C17E -34.8(12) . . . . ?
O16A P16 O16B C17E 91.0(12) . . . . ?
C17 P16 O16B C17E -160.7(12) . . . . ?
O16 P16 O16B C17B -49.4(13) . . . . ?
O16A P16 O16B C17B 76.4(13) . . . . ?
C17 P16 O16B C17B -175.3(13) . . . . ?
C25 N24 C17 C18 -108.0(3) . . . . ?
C25 N24 C17 P16 126.4(2) . . . . ?
O16 P16 C17 N24 73.1(2) . . . . ?
O16B P16 C17 N24 -160.55(18) . . . . ?
O16A P16 C17 N24 -53.7(2) . . . . ?
O16 P16 C17 C18 -49.9(2) . . . . ?
O16B P16 C17 C18 76.5(2) . . . . ?
O16A P16 C17 C18 -176.7(2) . . . . ?
C19C N19 C18 C23 -93.9(3) . . . . ?
C20 N19 C18 C23 56.9(3) . . . . ?
C19C N19 C18 C17 141.3(2) . . . . ?
C20 N19 C18 C17 -67.9(3) . . . . ?
N24 C17 C18 N19 179.2(2) . . . . ?
P16 C17 C18 N19 -56.8(3) . . . . ?
N24 C17 C18 C23 56.0(3) . . . . ?
P16 C17 C18 C23 180.0(2) . . . . ?
C19C N19 C20 C21 91.7(4) . . . . ?
C18 N19 C20 C21 -57.6(3) . . . . ?
N19 C20 C21 C22 53.7(4) . . . . ?
C20 C21 C22 C23 -52.5(4) . . . . ?
C21 C22 C23 C18 53.4(4) . . . . ?
N19 C18 C23 C22 -54.4(3) . . . . ?
C17 C18 C23 C22 71.1(3) . . . . ?
C17 N24 C25 O25 -15.3(4) . . . . ?
C17 N24 C25 C26 162.6(2) . . . . ?
O25 C25 C26 C30 174.3(4) . . . . ?
N24 C25 C26 C30 -3.6(5) . . . . ?
O25 C25 C26 S27 0.5(4) . . . . ?
N24 C25 C26 S27 -177.4(2) . . . . ?
C28 S27 C26 C30 1.6(3) . . . . ?
C28 S27 C26 C25 176.6(3) . . . . ?
C26 S27 C28 C29 -1.6(4) . . . . ?
S27 C28 C29 C30 1.2(6) . . . . ?
C25 C26 C30 C29 -175.3(4) . . . . ?
S27 C26 C30 C29 -1.2(5) . . . . ?
C28 C29 C30 C26 0.0(6) . . . . ?
P16 O16A C17A C18A 131.4(11) . . . . ?
P16 O16A C17D C18D 141.2(13) . . . . ?
P16 O16B C17B C18B 115.8(15) . . . . ?
P16 O16B C17E C18E 163.6(12) . . . . ?
C21C O20C C19C O19C 9.2(5) . . . . ?
C21C O20C C19C N19 -172.5(3) . . . . ?
C18 N19 C19C O19C -19.0(4) . . . . ?
C20 N19 C19C O19C -167.5(3) . . . . ?
C18 N19 C19C O20C 162.7(2) . . . . ?
C20 N19 C19C O20C 14.2(4) . . . . ?
C19C O20C C21C C22C 54.5(5) . . . . ?
C19C O20C C21C C24C -68.6(4) . . . . ?
C19C O20C C21C C23C 173.8(3) . . . . ?
O31 P31 O31A C32D -21.3(11) . . . . ?
O31B P31 O31A C32D -147.5(11) . . . . ?
C32 P31 O31A C32D 105.6(11) . . . . ?
O31 P31 O31A C32A 6.9(9) . . . . ?
O31B P31 O31A C32A -119.4(9) . . . . ?
C32 P31 O31A C32A 133.8(9) . . . . ?
O31 P31 O31B C32E -41.8(9) . . . . ?
O31A P31 O31B C32E 83.6(8) . . . . ?
C32 P31 O31B C32E -167.2(8) . . . . ?
O31 P31 O31B C32B -57.1(10) . . . . ?
O31A P31 O31B C32B 68.4(9) . . . . ?
C32 P31 O31B C32B 177.6(9) . . . . ?
C40 N39 C32 C33 -114.8(3) . . . . ?
C40 N39 C32 P31 120.4(2) . . . . ?
O31 P31 C32 N39 78.6(2) . . . . ?
O31A P31 C32 N39 -48.1(2) . . . . ?
O31B P31 C32 N39 -155.34(19) . . . . ?
O31 P31 C32 C33 -45.6(2) . . . . ?
O31A P31 C32 C33 -172.27(19) . . . . ?
O31B P31 C32 C33 80.4(2) . . . . ?
C34C N34 C33 C38 -96.7(3) . . . . ?
C35 N34 C33 C38 56.6(3) . . . . ?
C34C N34 C33 C32 136.9(3) . . . . ?
C35 N34 C33 C32 -69.8(3) . . . . ?
N39 C32 C33 N34 169.1(2) . . . . ?
P31 C32 C33 N34 -67.3(3) . . . . ?
N39 C32 C33 C38 45.9(3) . . . . ?
P31 C32 C33 C38 169.5(2) . . . . ?
C34C N34 C35 C36 94.5(4) . . . . ?
C33 N34 C35 C36 -57.4(4) . . . . ?
N34 C35 C36 C37 54.3(4) . . . . ?
C35 C36 C37 C38 -53.4(4) . . . . ?
C36 C37 C38 C33 54.5(4) . . . . ?
N34 C33 C38 C37 -54.9(3) . . . . ?
C32 C33 C38 C37 69.3(3) . . . . ?
C32 N39 C40 O40 -8.2(4) . . . . ?
C32 N39 C40 C41 171.0(2) . . . . ?
O40 C40 C41 C45 -170.0(3) . . . . ?
N39 C40 C41 C45 10.8(5) . . . . ?
O40 C40 C41 S42 10.4(4) . . . . ?
N39 C40 C41 S42 -168.8(2) . . . . ?
C43 S42 C41 C45 -0.8(3) . . . . ?
C43 S42 C41 C40 178.8(3) . . . . ?
C41 S42 C43 C44 0.5(4) . . . . ?
S42 C43 C44 C45 0.0(5) . . . . ?
C40 C41 C45 C44 -178.6(3) . . . . ?
S42 C41 C45 C44 1.0(4) . . . . ?
C43 C44 C45 C41 -0.6(5) . . . . ?
P31 O31A C32A C33A 132.6(14) . . . . ?
P31 O31A C32D C33D 131.7(16) . . . . ?
P31 O31B C32B C33B 97.8(15) . . . . ?
P31 O31B C32E C33E 155.7(15) . . . . ?
C33 N34 C34C O34C -9.9(5) . . . . ?
C35 N34 C34C O34C -160.7(4) . . . . ?
C33 N34 C34C O35C 170.8(3) . . . . ?
C35 N34 C34C O35C 19.9(4) . . . . ?
C36C O35C C34C O34C 10.4(5) . . . . ?
C36C O35C C34C N34 -170.3(3) . . . . ?
C34C O35C C36C C39C -62.6(4) . . . . ?
C34C O35C C36C C38C 178.9(3) . . . . ?
C34C O35C C36C C37C 61.6(4) . . . . ?
O46 P46 O46A C47A 36.2(5) . . . . ?
O46B P46 O46A C47A 163.5(5) . . . . ?
C47 P46 O46A C47A -90.7(5) . . . . ?
O46 P46 O46A C47D -2.7(7) . . . . ?
O46B P46 O46A C47D 124.5(7) . . . . ?
C47 P46 O46A C47D -129.6(7) . . . . ?
O46 P46 O46B C47E 60.7(5) . . . . ?
O46A P46 O46B C47E -65.1(5) . . . . ?
C47 P46 O46B C47E -173.5(5) . . . . ?
O46 P46 O46B C47B 38.9(4) . . . . ?
O46A P46 O46B C47B -86.8(4) . . . . ?
C47 P46 O46B C47B 164.7(4) . . . . ?
C55 N54 C47 C48 113.1(3) . . . . ?
C55 N54 C47 P46 -122.2(2) . . . . ?
O46 P46 C47 N54 -74.7(2) . . . . ?
O46B P46 C47 N54 158.36(18) . . . . ?
O46A P46 C47 N54 51.8(2) . . . . ?
O46 P46 C47 C48 49.2(2) . . . . ?
O46B P46 C47 C48 -77.8(2) . . . . ?
O46A P46 C47 C48 175.66(19) . . . . ?
C49C N49 C48 C53 103.4(3) . . . . ?
C50 N49 C48 C53 -55.1(3) . . . . ?
C49C N49 C48 C47 -130.9(3) . . . . ?
C50 N49 C48 C47 70.6(3) . . . . ?
N54 C47 C48 N49 -175.8(2) . . . . ?
P46 C47 C48 N49 61.5(3) . . . . ?
N54 C47 C48 C53 -52.2(3) . . . . ?
P46 C47 C48 C53 -174.9(2) . . . . ?
C49C N49 C50 C51 -100.1(3) . . . . ?
C48 N49 C50 C51 57.3(3) . . . . ?
N49 C50 C51 C52 -55.2(4) . . . . ?
C50 C51 C52 C53 54.2(4) . . . . ?
C51 C52 C53 C48 -53.6(4) . . . . ?
N49 C48 C53 C52 52.4(4) . . . . ?
C47 C48 C53 C52 -72.2(4) . . . . ?
C47 N54 C55 O55 2.9(5) . . . . ?
C47 N54 C55 C56 -176.6(3) . . . . ?
O55 C55 C56 C60 166.7(3) . . . . ?
N54 C55 C56 C60 -13.8(5) . . . . ?
O55 C55 C56 S57 -12.4(4) . . . . ?
N54 C55 C56 S57 167.1(2) . . . . ?
C58 S57 C56 C60 -0.3(3) . . . . ?
C58 S57 C56 C55 178.9(3) . . . . ?
C56 S57 C58 C59 0.4(3) . . . . ?
S57 C58 C59 C60 -0.3(5) . . . . ?
C55 C56 C60 C59 -178.9(3) . . . . ?
S57 C56 C60 C59 0.2(4) . . . . ?
C58 C59 C60 C56 0.0(5) . . . . ?
P46 O46A C47A C48A -123.6(7) . . . . ?
P46 O46A C47D C48D 175.0(9) . . . . ?
P46 O46B C47B C48B -120.5(8) . . . . ?
P46 O46B C47E C48E -117.3(8) . . . . ?
C51C O50C C49C O49C -12.0(5) . . . . ?
C51C O50C C49C N49 169.7(3) . . . . ?
C48 N49 C49C O49C 13.0(4) . . . . ?
C50 N49 C49C O49C 169.7(3) . . . . ?
C48 N49 C49C O50C -168.7(2) . . . . ?
C50 N49 C49C O50C -12.0(4) . . . . ?
C49C O50C C51C C54C -52.6(5) . . . . ?
C49C O50C C51C C53C -173.1(3) . . . . ?
C49C O50C C51C C52C 69.4(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N9 H9 O16 0.908(17) 1.946(19) 2.834(3) 166(3) . yes
N24 H24 O1 0.886(17) 2.080(19) 2.927(3) 160(3) . yes
N39 H39 O46 0.866(17) 2.041(18) 2.886(3) 165(3) . yes
N54 H54 O31 0.905(17) 1.980(18) 2.865(3) 165(3) . yes

_refine_diff_density_max         0.367
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_4i-1
_database_code_depnum_ccdc_archive 'CCDC 2209101'
loop_
_audit_author_name
_audit_author_address
'Arto Valkonen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2023-03-07 deposited with the CCDC.	2023-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C21 H35 N2 O6 P S'
_chemical_formula_sum            'C21 H35 N2 O6 P S'
_chemical_formula_weight         474.54

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'
S S 0.1246 0.1234 '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'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2861(6)
_cell_length_b                   11.2061(9)
_cell_length_c                   12.3620(6)
_cell_angle_alpha                103.022(5)
_cell_angle_beta                 100.213(5)
_cell_angle_gamma                102.017(6)
_cell_volume                     1191.44(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    5547
_cell_measurement_theta_min      2.9220
_cell_measurement_theta_max      29.7450

_exptl_crystal_description       'stacked plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_F_000             508
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.242
_shelx_estimated_absorpt_T_min   0.935
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.629
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0107
_diffrn_reflns_number            18917
_diffrn_reflns_av_unetI/netI     0.0649
_diffrn_reflns_av_R_equivalents  0.0728
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.219
_diffrn_reflns_theta_max         29.949
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.904
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.904
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.904
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6250
_reflns_number_gt                4561
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    SHELXL-2019/2
_computing_publication_material  SHELXL-2019/2
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1179P)²+0.1893P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6250
_refine_ls_number_parameters     340
_refine_ls_number_restraints     128
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0702
_refine_ls_wR_factor_ref         0.2123
_refine_ls_wR_factor_gt          0.1820
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S13 S 0.7748(3) 0.4536(3) 0.02835(16) 0.0312(4) Uani 0.612(3) 1 d D U P A 1
S13B S 0.8157(5) 0.4038(5) 0.2474(3) 0.0327(7) Uani 0.388(3) 1 d D U P A 2
P1 P 0.46607(7) 0.72096(6) 0.52148(5) 0.03078(19) Uani 1 1 d D . . . .
O1 O 0.39751(19) 0.61204(17) 0.55893(14) 0.0377(4) Uani 1 1 d . . . . .
O10 O 0.70682(19) 0.74915(15) 0.27711(13) 0.0339(4) Uani 1 1 d . . . . .
O1A O 0.36003(18) 0.74058(15) 0.41586(13) 0.0334(4) Uani 1 1 d . . . . .
O1B O 0.5221(4) 0.8595(3) 0.6084(3) 0.0343(7) Uani 0.781(7) 1 d D . P B 1
O1D O 0.4675(14) 0.8325(10) 0.6206(8) 0.028(2) Uani 0.219(7) 1 d D . P B 2
O4C O 0.68482(19) 0.66814(15) 0.77294(13) 0.0347(4) Uani 1 1 d . . . . .
O5C O 0.78070(17) 0.88031(14) 0.85753(12) 0.0286(3) Uani 1 1 d . . . . .
N4 N 0.8031(2) 0.79878(18) 0.68042(15) 0.0304(4) Uani 1 1 d . . . . .
N9 N 0.6086(2) 0.61660(18) 0.37464(15) 0.0289(4) Uani 1 1 d D . . . .
H9 H 0.575(3) 0.5373(17) 0.376(2) 0.031(6) Uiso 1 1 d D . . . .
C2 C 0.6441(3) 0.7156(2) 0.48111(17) 0.0292(5) Uani 1 1 d . . . . .
H2 H 0.685770 0.798261 0.465692 0.035 Uiso 1 1 calc R U . . .
C3 C 0.7662(3) 0.6958(2) 0.57416(17) 0.0304(5) Uani 1 1 d . . . . .
H3 H 0.725108 0.613880 0.590912 0.037 Uiso 1 1 calc R U . . .
C5 C 0.8868(3) 0.9238(2) 0.67905(19) 0.0325(5) Uani 1 1 d . . . . .
H5A H 0.910865 0.983106 0.756300 0.039 Uiso 1 1 calc R U . . .
H5B H 0.823704 0.956987 0.625732 0.039 Uiso 1 1 calc R U . . .
C6 C 1.0329(3) 0.9152(3) 0.6416(2) 0.0391(6) Uani 1 1 d . . . . .
H6A H 1.101349 0.892683 0.700283 0.047 Uiso 1 1 calc R U . . .
H6B H 1.084562 0.998856 0.634588 0.047 Uiso 1 1 calc R U . . .
C7 C 1.0006(3) 0.8158(3) 0.5272(2) 0.0423(6) Uani 1 1 d . . . . .
H7A H 0.942684 0.843565 0.466593 0.051 Uiso 1 1 calc R U . . .
H7B H 1.097496 0.807199 0.507580 0.051 Uiso 1 1 calc R U . . .
C8 C 0.9113(3) 0.6890(3) 0.53254(19) 0.0382(6) Uani 1 1 d . . . . .
H8A H 0.976140 0.655654 0.584516 0.046 Uiso 1 1 calc R U . . .
H8B H 0.883826 0.628655 0.455556 0.046 Uiso 1 1 calc R U . . .
C10 C 0.6439(2) 0.6432(2) 0.27949(18) 0.0276(4) Uani 1 1 d . . . . .
C11 C 0.5958(2) 0.5303(2) 0.17383(18) 0.0306(5) Uani 1 1 d . . . . .
H11A H 0.509870 0.466803 0.182223 0.037 Uiso 1 1 calc R U . . .
H11B H 0.559757 0.559044 0.106265 0.037 Uiso 1 1 calc R U . . .
C12 C 0.7202(2) 0.4683(2) 0.15326(17) 0.0284(4) Uani 1 1 d D U . . .
C14 C 0.9006(14) 0.3702(10) 0.0680(9) 0.0299(14) Uani 0.612(3) 1 d D U P A 1
H14 H 0.963062 0.338603 0.021641 0.036 Uiso 0.612(3) 1 calc R U P A 1
C15 C 0.9000(9) 0.3546(10) 0.1746(7) 0.0329(13) Uani 0.612(3) 1 d D U P A 1
H15 H 0.961775 0.310885 0.211555 0.039 Uiso 0.612(3) 1 calc R U P A 1
C16 C 0.7943(14) 0.4126(12) 0.2230(9) 0.041(2) Uani 0.612(3) 1 d D U P A 1
H16 H 0.777935 0.412031 0.296580 0.049 Uiso 0.612(3) 1 calc R U P A 1
C14B C 0.9296(14) 0.3603(16) 0.1576(11) 0.0317(19) Uani 0.388(3) 1 d D U P A 2
H14B H 1.008416 0.321121 0.176490 0.038 Uiso 0.388(3) 1 calc R U P A 2
C15B C 0.893(2) 0.3889(17) 0.0559(15) 0.035(2) Uani 0.388(3) 1 d D U P A 2
H15B H 0.942422 0.371890 -0.004711 0.042 Uiso 0.388(3) 1 calc R U P A 2
C16B C 0.771(2) 0.4476(17) 0.0535(10) 0.035(3) Uani 0.388(3) 1 d D U P A 2
H16B H 0.726983 0.470636 -0.011743 0.042 Uiso 0.388(3) 1 calc R U P A 2
C2A C 0.2335(3) 0.6389(2) 0.3395(2) 0.0379(5) Uani 1 1 d . . . . .
H2A H 0.168088 0.600436 0.384322 0.045 Uiso 1 1 calc R U . . .
H2B H 0.271880 0.572043 0.295570 0.045 Uiso 1 1 calc R U . . .
C3A C 0.1453(3) 0.6943(3) 0.2603(2) 0.0419(6) Uani 1 1 d . . . . .
H3A H 0.059664 0.627549 0.208170 0.063 Uiso 1 1 calc R U . . .
H3B H 0.107372 0.760065 0.304473 0.063 Uiso 1 1 calc R U . . .
H3C H 0.210797 0.731773 0.216036 0.063 Uiso 1 1 calc R U . . .
C2B C 0.4138(3) 0.9167(3) 0.6589(3) 0.0353(9) Uani 0.781(7) 1 d D . P B 1
H2C H 0.366704 0.864588 0.704595 0.042 Uiso 0.781(7) 1 calc R U P B 1
H2D H 0.332814 0.923730 0.598606 0.042 Uiso 0.781(7) 1 calc R U P B 1
C3B C 0.5010(3) 1.0448(2) 0.7333(2) 0.0373(5) Uani 1 1 d D . . . .
H3D H 0.432712 1.087332 0.769493 0.056 Uiso 0.781(7) 1 calc R U P B 1
H3E H 0.580745 1.036210 0.792411 0.056 Uiso 0.781(7) 1 calc R U P B 1
H3F H 0.547025 1.095056 0.686954 0.056 Uiso 0.781(7) 1 calc R U P B 1
H3G H 0.508365 1.132471 0.730427 0.056 Uiso 0.219(7) 1 calc R U P B 2
H3H H 0.415037 1.015726 0.765212 0.056 Uiso 0.219(7) 1 calc R U P B 2
H3I H 0.594627 1.040554 0.781642 0.056 Uiso 0.219(7) 1 calc R U P B 2
C2D C 0.4776(12) 0.9594(8) 0.6120(7) 0.027(3) Uani 0.219(7) 1 d D . P B 2
H2E H 0.383375 0.963022 0.562255 0.032 Uiso 0.219(7) 1 calc R U P B 2
H2F H 0.563716 0.987954 0.578754 0.032 Uiso 0.219(7) 1 calc R U P B 2
C4C C 0.7497(2) 0.7732(2) 0.77094(17) 0.0278(4) Uani 1 1 d . . . . .
C6C C 0.7328(3) 0.8769(2) 0.96494(17) 0.0294(5) Uani 1 1 d . . . . .
C7C C 0.8104(3) 0.7948(3) 1.0240(2) 0.0379(5) Uani 1 1 d . . . . .
H7C H 0.777723 0.793245 1.094968 0.057 Uiso 1 1 calc R U . . .
H7D H 0.783155 0.708307 0.973655 0.057 Uiso 1 1 calc R U . . .
H7E H 0.920383 0.829558 1.041649 0.057 Uiso 1 1 calc R U . . .
C8C C 0.7897(3) 1.0149(2) 1.03399(19) 0.0347(5) Uani 1 1 d . . . . .
H8C H 0.763855 1.024294 1.108423 0.052 Uiso 1 1 calc R U . . .
H8D H 0.899897 1.042364 1.045264 0.052 Uiso 1 1 calc R U . . .
H8E H 0.742025 1.067220 0.992857 0.052 Uiso 1 1 calc R U . . .
C9C C 0.5614(3) 0.8335(2) 0.9406(2) 0.0359(5) Uani 1 1 d . . . . .
H9C H 0.530435 0.831442 1.012017 0.054 Uiso 1 1 calc R U . . .
H9D H 0.517189 0.892660 0.906715 0.054 Uiso 1 1 calc R U . . .
H9E H 0.526016 0.748505 0.887219 0.054 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S13 C12 1.693(3) . ?
S13 C14 1.714(9) . ?
S13B C12 1.715(4) . ?
S13B C14B 1.725(12) . ?
P1 O1 1.4646(18) . ?
P1 O1D 1.537(8) . ?
P1 O1A 1.5768(17) . ?
P1 O1B 1.596(3) . ?
P1 C2 1.818(2) . ?
O10 C10 1.219(3) . ?
O1A C2A 1.461(3) . ?
O1B C2B 1.458(4) . ?
O1D C2D 1.435(14) . ?
O4C C4C 1.213(3) . ?
O5C C4C 1.356(2) . ?
O5C C6C 1.479(2) . ?
N4 C4C 1.364(3) . ?
N4 C5 1.459(3) . ?
N4 C3 1.472(3) . ?
N9 C10 1.354(3) . ?
N9 C2 1.452(3) . ?
N9 H9 0.884(17) . ?
C2 C3 1.554(3) . ?
C2 H2 1.0000 . ?
C3 C8 1.535(3) . ?
C3 H3 1.0000 . ?
C5 C6 1.523(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.527(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.511(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C10 C11 1.523(3) . ?
C11 C12 1.497(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C16 1.347(9) . ?
C12 C16B 1.384(11) . ?
C14 C15 1.368(8) . ?
C14 H14 0.9500 . ?
C15 C16 1.430(14) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C14B C15B 1.368(12) . ?
C14B H14B 0.9500 . ?
C15B C16B 1.43(2) . ?
C15B H15B 0.9500 . ?
C16B H16B 0.9500 . ?
C2A C3A 1.489(4) . ?
C2A H2A 0.9900 . ?
C2A H2B 0.9900 . ?
C3A H3A 0.9800 . ?
C3A H3B 0.9800 . ?
C3A H3C 0.9800 . ?
C2B C3B 1.490(4) . ?
C2B H2C 0.9900 . ?
C2B H2D 0.9900 . ?
C3B C2D 1.537(9) . ?
C3B H3D 0.9800 . ?
C3B H3E 0.9800 . ?
C3B H3F 0.9800 . ?
C3B H3G 0.9800 . ?
C3B H3H 0.9800 . ?
C3B H3I 0.9800 . ?
C2D H2E 0.9900 . ?
C2D H2F 0.9900 . ?
C6C C7C 1.513(3) . ?
C6C C9C 1.517(3) . ?
C6C C8C 1.519(3) . ?
C7C H7C 0.9800 . ?
C7C H7D 0.9800 . ?
C7C H7E 0.9800 . ?
C8C H8C 0.9800 . ?
C8C H8D 0.9800 . ?
C8C H8E 0.9800 . ?
C9C H9C 0.9800 . ?
C9C H9D 0.9800 . ?
C9C H9E 0.9800 . ?

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
C12 S13 C14 91.9(4) . . ?
C12 S13B C14B 92.9(6) . . ?
O1 P1 O1D 101.6(5) . . ?
O1 P1 O1A 113.35(10) . . ?
O1D P1 O1A 103.3(4) . . ?
O1 P1 O1B 120.28(15) . . ?
O1A P1 O1B 103.03(14) . . ?
O1 P1 C2 114.91(10) . . ?
O1D P1 C2 117.6(5) . . ?
O1A P1 C2 105.68(9) . . ?
O1B P1 C2 97.45(14) . . ?
C2A O1A P1 122.40(15) . . ?
C2B O1B P1 119.9(3) . . ?
C2D O1D P1 124.1(8) . . ?
C4C O5C C6C 120.82(17) . . ?
C4C N4 C5 124.41(18) . . ?
C4C N4 C3 118.25(19) . . ?
C5 N4 C3 117.23(17) . . ?
C10 N9 C2 120.83(19) . . ?
C10 N9 H9 120.7(17) . . ?
C2 N9 H9 118.0(17) . . ?
N9 C2 C3 111.87(17) . . ?
N9 C2 P1 106.97(15) . . ?
C3 C2 P1 114.20(14) . . ?
N9 C2 H2 107.9 . . ?
C3 C2 H2 107.9 . . ?
P1 C2 H2 107.9 . . ?
N4 C3 C8 109.34(19) . . ?
N4 C3 C2 110.97(17) . . ?
C8 C3 C2 111.03(17) . . ?
N4 C3 H3 108.5 . . ?
C8 C3 H3 108.5 . . ?
C2 C3 H3 108.5 . . ?
N4 C5 C6 110.04(19) . . ?
N4 C5 H5A 109.7 . . ?
C6 C5 H5A 109.7 . . ?
N4 C5 H5B 109.7 . . ?
C6 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
C5 C6 C7 111.0(2) . . ?
C5 C6 H6A 109.4 . . ?
C7 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
C7 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C8 C7 C6 110.7(2) . . ?
C8 C7 H7A 109.5 . . ?
C6 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C7 C8 C3 113.2(2) . . ?
C7 C8 H8A 108.9 . . ?
C3 C8 H8A 108.9 . . ?
C7 C8 H8B 108.9 . . ?
C3 C8 H8B 108.9 . . ?
H8A C8 H8B 107.8 . . ?
O10 C10 N9 123.2(2) . . ?
O10 C10 C11 122.09(19) . . ?
N9 C10 C11 114.7(2) . . ?
C12 C11 C10 113.38(18) . . ?
C12 C11 H11A 108.9 . . ?
C10 C11 H11A 108.9 . . ?
C12 C11 H11B 108.9 . . ?
C10 C11 H11B 108.9 . . ?
H11A C11 H11B 107.7 . . ?
C16 C12 C11 126.9(6) . . ?
C16B C12 C11 125.6(7) . . ?
C16 C12 S13 112.3(5) . . ?
C11 C12 S13 120.69(18) . . ?
C16B C12 S13B 109.2(7) . . ?
C11 C12 S13B 125.1(2) . . ?
C15 C14 S13 111.8(10) . . ?
C15 C14 H14 124.1 . . ?
S13 C14 H14 124.1 . . ?
C14 C15 C16 111.1(10) . . ?
C14 C15 H15 124.4 . . ?
C16 C15 H15 124.4 . . ?
C12 C16 C15 113.0(9) . . ?
C12 C16 H16 123.5 . . ?
C15 C16 H16 123.5 . . ?
C15B C14B S13B 112.0(16) . . ?
C15B C14B H14B 124.0 . . ?
S13B C14B H14B 124.0 . . ?
C14B C15B C16B 110.7(18) . . ?
C14B C15B H15B 124.6 . . ?
C16B C15B H15B 124.6 . . ?
C12 C16B C15B 114.9(13) . . ?
C12 C16B H16B 122.5 . . ?
C15B C16B H16B 122.5 . . ?
O1A C2A C3A 108.1(2) . . ?
O1A C2A H2A 110.1 . . ?
C3A C2A H2A 110.1 . . ?
O1A C2A H2B 110.1 . . ?
C3A C2A H2B 110.1 . . ?
H2A C2A H2B 108.4 . . ?
C2A C3A H3A 109.5 . . ?
C2A C3A H3B 109.5 . . ?
H3A C3A H3B 109.5 . . ?
C2A C3A H3C 109.5 . . ?
H3A C3A H3C 109.5 . . ?
H3B C3A H3C 109.5 . . ?
O1B C2B C3B 106.4(3) . . ?
O1B C2B H2C 110.5 . . ?
C3B C2B H2C 110.5 . . ?
O1B C2B H2D 110.5 . . ?
C3B C2B H2D 110.5 . . ?
H2C C2B H2D 108.6 . . ?
C2B C3B H3D 109.5 . . ?
C2B C3B H3E 109.5 . . ?
H3D C3B H3E 109.5 . . ?
C2B C3B H3F 109.5 . . ?
H3D C3B H3F 109.5 . . ?
H3E C3B H3F 109.5 . . ?
C2D C3B H3G 109.5 . . ?
C2D C3B H3H 109.5 . . ?
H3G C3B H3H 109.5 . . ?
C2D C3B H3I 109.5 . . ?
H3G C3B H3I 109.5 . . ?
H3H C3B H3I 109.5 . . ?
O1D C2D C3B 107.4(7) . . ?
O1D C2D H2E 110.2 . . ?
C3B C2D H2E 110.2 . . ?
O1D C2D H2F 110.2 . . ?
C3B C2D H2F 110.2 . . ?
H2E C2D H2F 108.5 . . ?
O4C C4C O5C 125.22(19) . . ?
O4C C4C N4 124.02(19) . . ?
O5C C4C N4 110.75(19) . . ?
O5C C6C C7C 110.26(17) . . ?
O5C C6C C9C 109.86(18) . . ?
C7C C6C C9C 112.8(2) . . ?
O5C C6C C8C 102.18(17) . . ?
C7C C6C C8C 110.5(2) . . ?
C9C C6C C8C 110.73(18) . . ?
C6C C7C H7C 109.5 . . ?
C6C C7C H7D 109.5 . . ?
H7C C7C H7D 109.5 . . ?
C6C C7C H7E 109.5 . . ?
H7C C7C H7E 109.5 . . ?
H7D C7C H7E 109.5 . . ?
C6C C8C H8C 109.5 . . ?
C6C C8C H8D 109.5 . . ?
H8C C8C H8D 109.5 . . ?
C6C C8C H8E 109.5 . . ?
H8C C8C H8E 109.5 . . ?
H8D C8C H8E 109.5 . . ?
C6C C9C H9C 109.5 . . ?
C6C C9C H9D 109.5 . . ?
H9C C9C H9D 109.5 . . ?
C6C C9C H9E 109.5 . . ?
H9C C9C H9E 109.5 . . ?
H9D C9C H9E 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
O1 P1 O1A C2A -20.31(19) . . . . ?
O1D P1 O1A C2A -129.5(5) . . . . ?
O1B P1 O1A C2A -151.9(2) . . . . ?
C2 P1 O1A C2A 106.39(17) . . . . ?
O1 P1 O1B C2B -61.2(3) . . . . ?
O1A P1 O1B C2B 66.2(3) . . . . ?
C2 P1 O1B C2B 174.2(3) . . . . ?
O1 P1 O1D C2D -159.1(10) . . . . ?
O1A P1 O1D C2D -41.4(11) . . . . ?
C2 P1 O1D C2D 74.5(11) . . . . ?
C10 N9 C2 C3 -113.4(2) . . . . ?
C10 N9 C2 P1 120.80(19) . . . . ?
O1 P1 C2 N9 70.43(17) . . . . ?
O1D P1 C2 N9 -170.0(5) . . . . ?
O1A P1 C2 N9 -55.32(16) . . . . ?
O1B P1 C2 N9 -161.15(18) . . . . ?
O1 P1 C2 C3 -53.92(19) . . . . ?
O1D P1 C2 C3 65.7(5) . . . . ?
O1A P1 C2 C3 -179.67(15) . . . . ?
O1B P1 C2 C3 74.5(2) . . . . ?
C4C N4 C3 C8 -131.2(2) . . . . ?
C5 N4 C3 C8 52.5(2) . . . . ?
C4C N4 C3 C2 106.0(2) . . . . ?
C5 N4 C3 C2 -70.3(2) . . . . ?
N9 C2 C3 N4 178.68(17) . . . . ?
P1 C2 C3 N4 -59.6(2) . . . . ?
N9 C2 C3 C8 56.9(2) . . . . ?
P1 C2 C3 C8 178.54(16) . . . . ?
C4C N4 C5 C6 128.6(2) . . . . ?
C3 N4 C5 C6 -55.4(3) . . . . ?
N4 C5 C6 C7 54.3(3) . . . . ?
C5 C6 C7 C8 -54.8(3) . . . . ?
C6 C7 C8 C3 53.4(3) . . . . ?
N4 C3 C8 C7 -50.3(3) . . . . ?
C2 C3 C8 C7 72.5(2) . . . . ?
C2 N9 C10 O10 0.4(3) . . . . ?
C2 N9 C10 C11 -178.42(18) . . . . ?
O10 C10 C11 C12 84.4(3) . . . . ?
N9 C10 C11 C12 -96.7(2) . . . . ?
C10 C11 C12 C16 61.4(7) . . . . ?
C10 C11 C12 C16B -125.0(9) . . . . ?
C10 C11 C12 S13 -122.8(2) . . . . ?
C10 C11 C12 S13B 58.9(3) . . . . ?
C14 S13 C12 C16 0.1(8) . . . . ?
C14 S13 C12 C11 -176.2(4) . . . . ?
C14B S13B C12 C16B 3.9(10) . . . . ?
C14B S13B C12 C11 -179.4(5) . . . . ?
C12 S13 C14 C15 0.0(8) . . . . ?
S13 C14 C15 C16 -0.1(11) . . . . ?
C11 C12 C16 C15 175.9(6) . . . . ?
S13 C12 C16 C15 -0.2(11) . . . . ?
C14 C15 C16 C12 0.2(13) . . . . ?
C12 S13B C14B C15B -2.5(12) . . . . ?
S13B C14B C15B C16B 0.3(19) . . . . ?
C11 C12 C16B C15B 178.8(11) . . . . ?
S13B C12 C16B C15B -4.5(17) . . . . ?
C14B C15B C16B C12 3(2) . . . . ?
P1 O1A C2A C3A 172.03(15) . . . . ?
P1 O1B C2B C3B -179.1(2) . . . . ?
P1 O1D C2D C3B -171.2(8) . . . . ?
C6C O5C C4C O4C -1.2(3) . . . . ?
C6C O5C C4C N4 179.50(17) . . . . ?
C5 N4 C4C O4C -177.3(2) . . . . ?
C3 N4 C4C O4C 6.7(3) . . . . ?
C5 N4 C4C O5C 2.0(3) . . . . ?
C3 N4 C4C O5C -173.99(17) . . . . ?
C4C O5C C6C C7C 62.9(3) . . . . ?
C4C O5C C6C C9C -62.0(2) . . . . ?
C4C O5C C6C C8C -179.63(18) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N9 H9 O1 0.884(17) 2.06(2) 2.854(3) 150(2) 2_666 yes

_refine_diff_density_max         0.812
_refine_diff_density_min         -0.853
_refine_diff_density_rms         0.095


_exptl_crystal_recrystallization_method 'Vapour deposition'
####################################################################### 
# 
# 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_4d-2
_database_code_depnum_ccdc_archive 'CCDC 2203662'
loop_
_audit_author_name
_audit_author_address
'Arto Valkonen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2022-08-26 deposited with the CCDC.	2023-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H39 N2 O6 P S'
_chemical_formula_sum            'C24 H39 N2 O6 P S'
_chemical_formula_weight         514.60

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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   18.2265(2)
_cell_length_b                   14.9162(2)
_cell_length_c                   19.3281(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.2810(10)
_cell_angle_gamma                90
_cell_volume                     5253.42(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9628
_cell_measurement_theta_min      3.7240
_cell_measurement_theta_max      73.1480

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_F_000             2208
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    2.011
_shelx_estimated_absorpt_T_min   0.584
_shelx_estimated_absorpt_T_max   0.906
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.682
_exptl_absorpt_correction_T_max  0.924
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_reflns_number            20416
_diffrn_reflns_av_unetI/netI     0.0530
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.744
_diffrn_reflns_theta_max         73.383
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_point_group_measured_fraction_full 0.981
_reflns_number_total             10055
_reflns_number_gt                8632
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    SHELXL-2018/3
_computing_publication_material  SHELXL-2018/3
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0573P)²+2.5936P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10055
_refine_ls_number_parameters     647
_refine_ls_number_restraints     69
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1191
_refine_ls_wR_factor_gt          0.1110
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.027
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S12 S 0.20881(3) 0.92387(4) 0.20462(3) 0.02829(12) Uani 1 1 d . . . . .
P1 P 0.15461(3) 0.52778(4) 0.31726(3) 0.02528(13) Uani 1 1 d . . . . .
O1 O 0.20714(8) 0.45598(10) 0.33393(9) 0.0292(3) Uani 1 1 d . . . . .
O10 O 0.12896(8) 0.79633(11) 0.29116(8) 0.0290(3) Uani 1 1 d . . . . .
O1A O 0.14606(8) 0.53846(12) 0.23686(9) 0.0345(4) Uani 1 1 d . . . . .
O1B O 0.07674(14) 0.51226(18) 0.35226(14) 0.0232(5) Uani 0.8 1 d . U P A 1
O1E O 0.0688(6) 0.5219(7) 0.3225(6) 0.0231(18) Uani 0.2 1 d . U P A 2
O4C O 0.29988(8) 0.84994(11) 0.47269(9) 0.0319(3) Uani 1 1 d . . . . .
O5C O 0.34717(7) 0.73272(10) 0.41333(8) 0.0266(3) Uani 1 1 d . . . . .
N4 N 0.23078(9) 0.72628(12) 0.44855(9) 0.0208(3) Uani 1 1 d . . . . .
N9 N 0.21753(9) 0.68981(11) 0.29958(8) 0.0197(3) Uani 1 1 d D . . . .
H9 H 0.2610(10) 0.6690(17) 0.2882(13) 0.024 Uiso 1 1 d D U . . .
C2 C 0.17835(10) 0.63885(13) 0.35097(10) 0.0186(4) Uani 1 1 d . . . . .
H2 H 0.131400 0.671143 0.359790 0.022 Uiso 1 1 calc R U . . .
C3 C 0.22272(10) 0.63551(13) 0.42021(10) 0.0194(4) Uani 1 1 d . . . . .
H3 H 0.272882 0.612370 0.410226 0.023 Uiso 1 1 calc R U . . .
C5 C 0.16556(11) 0.76728(14) 0.47824(10) 0.0236(4) Uani 1 1 d . . . . .
H5A H 0.128382 0.778137 0.441060 0.028 Uiso 1 1 calc R U . . .
H5B H 0.178980 0.825855 0.499027 0.028 Uiso 1 1 calc R U . . .
C6 C 0.13295(12) 0.70736(17) 0.53326(11) 0.0307(5) Uani 1 1 d . . . . .
H6A H 0.086135 0.733402 0.548741 0.037 Uiso 1 1 calc R U . . .
H6B H 0.167051 0.704113 0.573777 0.037 Uiso 1 1 calc R U . . .
C7 C 0.11925(12) 0.61355(16) 0.50507(12) 0.0301(5) Uani 1 1 d . . . . .
H7A H 0.080848 0.615690 0.468064 0.036 Uiso 1 1 calc R U . . .
H7B H 0.101703 0.574198 0.542483 0.036 Uiso 1 1 calc R U . . .
C8 C 0.19002(11) 0.57557(15) 0.47614(11) 0.0265(4) Uani 1 1 d . . . . .
H8A H 0.179916 0.515525 0.456304 0.032 Uiso 1 1 calc R U . . .
H8B H 0.226509 0.568249 0.514441 0.032 Uiso 1 1 calc R U . . .
C10 C 0.18900(10) 0.76648(13) 0.27374(10) 0.0197(4) Uani 1 1 d . . . . .
C11 C 0.23454(11) 0.81532(14) 0.22394(10) 0.0217(4) Uani 1 1 d . . . . .
C13 C 0.28651(12) 0.94103(15) 0.15738(10) 0.0260(4) Uani 1 1 d . . . . .
C14 C 0.30545(14) 1.03042(16) 0.12620(11) 0.0334(5) Uani 1 1 d . . . . .
H14A H 0.296229 1.078957 0.159844 0.040 Uiso 1 1 calc R U . . .
H14B H 0.274425 1.041338 0.084345 0.040 Uiso 1 1 calc R U . . .
C15 C 0.38646(15) 1.0299(2) 0.10713(13) 0.0458(7) Uani 1 1 d . . . . .
H15A H 0.396852 1.082467 0.077619 0.055 Uiso 1 1 calc R U . . .
H15B H 0.417347 1.034716 0.149756 0.055 Uiso 1 1 calc R U . . .
C16 C 0.40570(14) 0.9447(2) 0.06885(15) 0.0494(8) Uani 1 1 d . . . . .
H16A H 0.456418 0.949210 0.051885 0.059 Uiso 1 1 calc R U . . .
H16B H 0.372154 0.937493 0.028233 0.059 Uiso 1 1 calc R U . . .
C17 C 0.39953(14) 0.8626(2) 0.11604(15) 0.0513(8) Uani 1 1 d . . . . .
H17A H 0.401235 0.807207 0.087866 0.062 Uiso 1 1 calc R U . . .
H17B H 0.441503 0.861438 0.149440 0.062 Uiso 1 1 calc R U . . .
C18 C 0.32852(12) 0.86560(17) 0.15478(11) 0.0297(5) Uani 1 1 d . . . . .
C19 C 0.29927(12) 0.79250(17) 0.19301(11) 0.0294(5) Uani 1 1 d . . . . .
H19 H 0.321687 0.735144 0.196664 0.035 Uiso 1 1 calc R U . . .
C2A C 0.08673(14) 0.5846(2) 0.20243(15) 0.0426(6) Uani 1 1 d . . . . .
H2A H 0.084727 0.647783 0.217860 0.051 Uiso 1 1 calc R U . . .
H2B H 0.039362 0.555445 0.212599 0.051 Uiso 1 1 calc R U . . .
C3A C 0.10167(17) 0.5796(3) 0.12586(17) 0.0562(8) Uani 1 1 d . . . . .
H3A H 0.062369 0.610407 0.099866 0.084 Uiso 1 1 calc R U . . .
H3B H 0.148729 0.608565 0.116676 0.084 Uiso 1 1 calc R U . . .
H3C H 0.103595 0.516695 0.111442 0.084 Uiso 1 1 calc R U . . .
C2B C 0.04880(15) 0.4224(2) 0.36520(16) 0.0297(6) Uani 0.8 1 d D U P A 1
H2C H 0.015237 0.424265 0.404738 0.036 Uiso 0.8 1 calc R U P A 1
H2D H 0.090262 0.382274 0.377839 0.036 Uiso 0.8 1 calc R U P A 1
C3B C 0.0089(2) 0.3854(3) 0.3034(2) 0.0508(10) Uani 0.8 1 d D U P A 1
H3D H -0.009091 0.325081 0.313851 0.076 Uiso 0.8 1 calc R U P A 1
H3E H -0.032735 0.424359 0.291249 0.076 Uiso 0.8 1 calc R U P A 1
H3F H 0.042242 0.382395 0.264366 0.076 Uiso 0.8 1 calc R U P A 1
C2E C 0.0262(6) 0.4451(8) 0.2918(6) 0.0325(19) Uani 0.2 1 d D U P A 2
H2E H -0.022732 0.465922 0.275520 0.039 Uiso 0.2 1 calc R U P A 2
H2F H 0.052396 0.420184 0.251840 0.039 Uiso 0.2 1 calc R U P A 2
C3E C 0.0184(9) 0.3770(10) 0.3445(9) 0.045(3) Uani 0.2 1 d D U P A 2
H3G H -0.009339 0.326211 0.325268 0.067 Uiso 0.2 1 calc R U P A 2
H3H H 0.067136 0.356532 0.360194 0.067 Uiso 0.2 1 calc R U P A 2
H3I H -0.007745 0.402119 0.383796 0.067 Uiso 0.2 1 calc R U P A 2
C4C C 0.29338(11) 0.77585(14) 0.44669(10) 0.0216(4) Uani 1 1 d . . . . .
C6C C 0.41678(11) 0.77968(15) 0.40000(12) 0.0269(4) Uani 1 1 d . . . . .
C7C C 0.45733(13) 0.7982(2) 0.46783(14) 0.0415(6) Uani 1 1 d . . . . .
H7C H 0.503445 0.829370 0.458640 0.062 Uiso 1 1 calc R U . . .
H7D H 0.426829 0.835857 0.497189 0.062 Uiso 1 1 calc R U . . .
H7E H 0.467943 0.741432 0.491502 0.062 Uiso 1 1 calc R U . . .
C8C C 0.45638(14) 0.7130(2) 0.35551(19) 0.0517(8) Uani 1 1 d . . . . .
H8C H 0.504274 0.737409 0.343211 0.077 Uiso 1 1 calc R U . . .
H8D H 0.463387 0.656869 0.381161 0.077 Uiso 1 1 calc R U . . .
H8E H 0.427185 0.701428 0.313255 0.077 Uiso 1 1 calc R U . . .
C9C C 0.40238(14) 0.86496(19) 0.35927(14) 0.0408(6) Uani 1 1 d . . . . .
H9C1 H 0.449019 0.895314 0.350840 0.061 Uiso 1 1 calc R U . . .
H9C2 H 0.378247 0.850077 0.314925 0.061 Uiso 1 1 calc R U . . .
H9C3 H 0.370565 0.904609 0.385700 0.061 Uiso 1 1 calc R U . . .
S31 S 0.28070(3) 0.09189(3) 0.31289(2) 0.02053(11) Uani 1 1 d . . . . .
P20 P 0.38523(2) 0.49437(3) 0.24521(2) 0.01620(11) Uani 1 1 d . . . . .
O20 O 0.33987(7) 0.57487(9) 0.25585(7) 0.0217(3) Uani 1 1 d . . . . .
O29 O 0.36816(8) 0.21889(10) 0.23064(7) 0.0235(3) Uani 1 1 d . . . . .
O20A O 0.42183(7) 0.45591(10) 0.31395(7) 0.0209(3) Uani 1 1 d . . . . .
O20B O 0.45260(7) 0.50499(10) 0.19676(7) 0.0217(3) Uani 1 1 d . . . . .
O24C O 0.16618(7) 0.23785(10) 0.10508(7) 0.0219(3) Uani 1 1 d . . . . .
O23C O 0.14883(7) 0.35375(10) 0.17917(8) 0.0262(3) Uani 1 1 d . . . . .
N23 N 0.25103(8) 0.34689(11) 0.11343(8) 0.0186(3) Uani 1 1 d . . . . .
N28 N 0.30295(8) 0.34507(11) 0.25445(8) 0.0169(3) Uani 1 1 d D . . . .
H28 H 0.2631(11) 0.3684(16) 0.2750(12) 0.020 Uiso 1 1 d D U . . .
C21 C 0.33858(10) 0.40006(12) 0.20282(9) 0.0159(3) Uani 1 1 d . . . . .
H21 H 0.376710 0.362411 0.180380 0.019 Uiso 1 1 calc R U . . .
C22 C 0.28166(10) 0.42818(13) 0.14611(9) 0.0167(3) Uani 1 1 d . . . . .
H22 H 0.240766 0.460327 0.169228 0.020 Uiso 1 1 calc R U . . .
C24 C 0.29903(10) 0.29666(14) 0.06744(10) 0.0212(4) Uani 1 1 d . . . . .
H24A H 0.270937 0.247308 0.045136 0.025 Uiso 1 1 calc R U . . .
H24B H 0.339998 0.269933 0.094879 0.025 Uiso 1 1 calc R U . . .
C25 C 0.32978(11) 0.35814(15) 0.01184(10) 0.0244(4) Uani 1 1 d . . . . .
H25A H 0.289627 0.376175 -0.020575 0.029 Uiso 1 1 calc R U . . .
H25B H 0.366724 0.324925 -0.014839 0.029 Uiso 1 1 calc R U . . .
C26 C 0.36535(11) 0.44213(15) 0.04343(10) 0.0241(4) Uani 1 1 d . . . . .
H26A H 0.409880 0.425028 0.070576 0.029 Uiso 1 1 calc R U . . .
H26B H 0.380263 0.483160 0.006022 0.029 Uiso 1 1 calc R U . . .
C27 C 0.31158(11) 0.48995(14) 0.09033(10) 0.0213(4) Uani 1 1 d . . . . .
H27A H 0.270137 0.513566 0.061810 0.026 Uiso 1 1 calc R U . . .
H27B H 0.336643 0.541521 0.112800 0.026 Uiso 1 1 calc R U . . .
C29 C 0.31814(10) 0.25691(13) 0.26114(9) 0.0177(4) Uani 1 1 d . . . . .
C30 C 0.26995(10) 0.20667(13) 0.30784(9) 0.0174(4) Uani 1 1 d . . . . .
C32 C 0.20591(10) 0.08137(13) 0.36504(9) 0.0198(4) Uani 1 1 d . . . . .
C33 C 0.18017(12) -0.00729(14) 0.39255(11) 0.0251(4) Uani 1 1 d . . . . .
H33A H 0.213901 -0.027855 0.430149 0.030 Uiso 1 1 calc R U . . .
H33B H 0.180199 -0.052695 0.355197 0.030 Uiso 1 1 calc R U . . .
C34 C 0.10256(12) 0.00296(15) 0.42019(12) 0.0289(4) Uani 1 1 d . . . . .
H34A H 0.067050 0.008100 0.380878 0.035 Uiso 1 1 calc R U . . .
H34B H 0.089757 -0.051009 0.447188 0.035 Uiso 1 1 calc R U . . .
C35 C 0.09708(13) 0.08584(16) 0.46608(12) 0.0301(5) Uani 1 1 d . . . . .
H35A H 0.134237 0.081981 0.504114 0.036 Uiso 1 1 calc R U . . .
H35B H 0.047985 0.087817 0.486915 0.036 Uiso 1 1 calc R U . . .
C36 C 0.10934(12) 0.17172(15) 0.42465(12) 0.0290(4) Uani 1 1 d . . . . .
H36A H 0.065132 0.184642 0.395666 0.035 Uiso 1 1 calc R U . . .
H36B H 0.117078 0.222588 0.456892 0.035 Uiso 1 1 calc R U . . .
C37 C 0.17510(10) 0.16268(14) 0.37894(10) 0.0203(4) Uani 1 1 d . . . . .
C38 C 0.21165(10) 0.23489(14) 0.34608(10) 0.0203(4) Uani 1 1 d . . . . .
H38 H 0.197316 0.295864 0.350138 0.024 Uiso 1 1 calc R U . . .
C21A C 0.38498(12) 0.46205(15) 0.37997(10) 0.0275(4) Uani 1 1 d . . . . .
H21A H 0.333093 0.479587 0.371960 0.033 Uiso 1 1 calc R U . . .
H21B H 0.408954 0.508571 0.409178 0.033 Uiso 1 1 calc R U . . .
C22A C 0.38845(13) 0.37334(16) 0.41646(11) 0.0316(5) Uani 1 1 d . . . . .
H22A H 0.363591 0.377952 0.460760 0.047 Uiso 1 1 calc R U . . .
H22B H 0.364161 0.327595 0.387663 0.047 Uiso 1 1 calc R U . . .
H22C H 0.439865 0.356519 0.424804 0.047 Uiso 1 1 calc R U . . .
C21B C 0.50696(11) 0.57598(16) 0.20638(11) 0.0286(5) Uani 1 1 d . . . . .
H21C H 0.555181 0.549699 0.219464 0.034 Uiso 1 1 calc R U . . .
H21D H 0.491946 0.616787 0.243903 0.034 Uiso 1 1 calc R U . . .
C22B C 0.51264(18) 0.6265(2) 0.14056(18) 0.0614(10) Uani 1 1 d . . . . .
H22D H 0.549018 0.674460 0.146313 0.092 Uiso 1 1 calc R U . . .
H22E H 0.527842 0.585764 0.103776 0.092 Uiso 1 1 calc R U . . .
H22F H 0.464806 0.652642 0.128138 0.092 Uiso 1 1 calc R U . . .
C23C C 0.18536(10) 0.31555(13) 0.13624(10) 0.0190(4) Uani 1 1 d . . . . .
C25C C 0.09715(10) 0.19373(14) 0.12434(11) 0.0227(4) Uani 1 1 d . . . . .
C27C C 0.09701(12) 0.11090(16) 0.07826(13) 0.0308(5) Uani 1 1 d . . . . .
H27C H 0.052825 0.075406 0.086542 0.046 Uiso 1 1 calc R U . . .
H27D H 0.097483 0.129357 0.029609 0.046 Uiso 1 1 calc R U . . .
H27E H 0.140645 0.074652 0.088977 0.046 Uiso 1 1 calc R U . . .
C26C C 0.03144(11) 0.25244(15) 0.10691(12) 0.0274(4) Uani 1 1 d . . . . .
H26C H -0.013606 0.221642 0.120189 0.041 Uiso 1 1 calc R U . . .
H26D H 0.035801 0.309195 0.132213 0.041 Uiso 1 1 calc R U . . .
H26E H 0.029628 0.264461 0.057051 0.041 Uiso 1 1 calc R U . . .
C28C C 0.10010(12) 0.16629(17) 0.20014(12) 0.0319(5) Uani 1 1 d . . . . .
H28A H 0.053877 0.137128 0.212031 0.048 Uiso 1 1 calc R U . . .
H28B H 0.140872 0.124449 0.208115 0.048 Uiso 1 1 calc R U . . .
H28C H 0.107447 0.219598 0.229102 0.048 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S12 C13 1.721(2) . ?
S12 C11 1.724(2) . ?
P1 O1 1.4677(17) . ?
P1 O1A 1.5664(18) . ?
P1 O1E 1.572(10) . ?
P1 O1B 1.603(3) . ?
P1 C2 1.829(2) . ?
O10 C10 1.235(2) . ?
O1A C2A 1.433(3) . ?
O1B C2B 1.458(4) . ?
O1E C2E 1.497(16) . ?
O4C C4C 1.218(3) . ?
O5C C4C 1.349(2) . ?
O5C C6C 1.477(2) . ?
N4 C4C 1.361(3) . ?
N4 C5 1.465(2) . ?
N4 C3 1.467(3) . ?
N9 C10 1.348(3) . ?
N9 C2 1.451(2) . ?
C2 C3 1.549(3) . ?
C3 C8 1.534(3) . ?
C5 C6 1.520(3) . ?
C6 C7 1.520(3) . ?
C7 C8 1.526(3) . ?
C10 C11 1.477(3) . ?
C11 C19 1.377(3) . ?
C13 C18 1.363(3) . ?
C13 C14 1.507(3) . ?
C14 C15 1.530(4) . ?
C15 C16 1.516(5) . ?
C16 C17 1.533(4) . ?
C17 C18 1.510(3) . ?
C18 C19 1.427(3) . ?
C2A C3A 1.513(4) . ?
C2B C3B 1.491(5) . ?
C2E C3E 1.448(15) . ?
C6C C8C 1.509(3) . ?
C6C C9C 1.516(4) . ?
C6C C7C 1.516(3) . ?
S31 C32 1.7205(19) . ?
S31 C30 1.726(2) . ?
P20 O20 1.4749(14) . ?
P20 O20B 1.5689(13) . ?
P20 O20A 1.5811(14) . ?
P20 C21 1.8280(19) . ?
O29 C29 1.235(2) . ?
O20A C21A 1.458(2) . ?
O20B C21B 1.459(2) . ?
O24C C23C 1.349(2) . ?
O24C C25C 1.475(2) . ?
O23C C23C 1.217(2) . ?
N23 C23C 1.367(2) . ?
N23 C24 1.467(2) . ?
N23 C22 1.472(2) . ?
N28 C29 1.349(3) . ?
N28 C21 1.456(2) . ?
C21 C22 1.550(2) . ?
C22 C27 1.528(3) . ?
C24 C25 1.529(3) . ?
C25 C26 1.531(3) . ?
C26 C27 1.527(3) . ?
C29 C30 1.478(3) . ?
C30 C38 1.374(3) . ?
C32 C37 1.366(3) . ?
C32 C33 1.504(3) . ?
C33 C34 1.531(3) . ?
C34 C35 1.526(3) . ?
C35 C36 1.530(3) . ?
C36 C37 1.511(3) . ?
C37 C38 1.423(3) . ?
C21A C22A 1.500(3) . ?
C21B C22B 1.484(4) . ?
C25C C26C 1.516(3) . ?
C25C C28C 1.521(3) . ?
C25C C27C 1.523(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 S12 C11 91.81(10) . . ?
O1 P1 O1A 110.00(9) . . ?
O1 P1 O1E 126.2(4) . . ?
O1A P1 O1E 89.6(4) . . ?
O1 P1 O1B 112.43(12) . . ?
O1A P1 O1B 111.35(12) . . ?
O1 P1 C2 115.78(9) . . ?
O1A P1 C2 106.19(9) . . ?
O1E P1 C2 104.8(4) . . ?
O1B P1 C2 100.68(11) . . ?
C2A O1A P1 124.53(16) . . ?
C2B O1B P1 121.4(2) . . ?
C2E O1E P1 121.7(8) . . ?
C4C O5C C6C 119.57(16) . . ?
C4C N4 C5 118.14(17) . . ?
C4C N4 C3 124.67(16) . . ?
C5 N4 C3 117.14(16) . . ?
C10 N9 C2 120.43(16) . . ?
N9 C2 C3 110.67(15) . . ?
N9 C2 P1 110.29(13) . . ?
C3 C2 P1 113.17(13) . . ?
N4 C3 C8 108.19(16) . . ?
N4 C3 C2 109.81(15) . . ?
C8 C3 C2 115.10(16) . . ?
N4 C5 C6 111.21(17) . . ?
C5 C6 C7 110.74(17) . . ?
C6 C7 C8 109.84(18) . . ?
C7 C8 C3 112.76(17) . . ?
O10 C10 N9 122.81(18) . . ?
O10 C10 C11 120.93(18) . . ?
N9 C10 C11 116.25(17) . . ?
C19 C11 C10 131.3(2) . . ?
C19 C11 S12 111.69(16) . . ?
C10 C11 S12 116.76(15) . . ?
C18 C13 C14 125.6(2) . . ?
C18 C13 S12 111.49(16) . . ?
C14 C13 S12 122.85(18) . . ?
C13 C14 C15 108.8(2) . . ?
C16 C15 C14 110.9(2) . . ?
C15 C16 C17 111.0(2) . . ?
C18 C17 C16 110.2(2) . . ?
C13 C18 C19 113.28(19) . . ?
C13 C18 C17 122.1(2) . . ?
C19 C18 C17 124.6(2) . . ?
C11 C19 C18 111.7(2) . . ?
O1A C2A C3A 106.3(2) . . ?
O1B C2B C3B 111.6(3) . . ?
C3E C2E O1E 108.4(12) . . ?
O4C C4C O5C 124.39(19) . . ?
O4C C4C N4 123.76(19) . . ?
O5C C4C N4 111.85(17) . . ?
O5C C6C C8C 102.15(17) . . ?
O5C C6C C9C 110.43(18) . . ?
C8C C6C C9C 109.7(2) . . ?
O5C C6C C7C 109.86(18) . . ?
C8C C6C C7C 112.5(2) . . ?
C9C C6C C7C 111.8(2) . . ?
C32 S31 C30 91.90(9) . . ?
O20 P20 O20B 116.73(8) . . ?
O20 P20 O20A 113.92(8) . . ?
O20B P20 O20A 102.54(7) . . ?
O20 P20 C21 115.62(8) . . ?
O20B P20 C21 99.94(8) . . ?
O20A P20 C21 106.30(8) . . ?
C21A O20A P20 121.24(13) . . ?
C21B O20B P20 122.37(13) . . ?
C23C O24C C25C 119.00(15) . . ?
C23C N23 C24 124.00(16) . . ?
C23C N23 C22 118.02(15) . . ?
C24 N23 C22 117.09(15) . . ?
C29 N28 C21 121.41(15) . . ?
N28 C21 C22 109.59(14) . . ?
N28 C21 P20 109.67(12) . . ?
C22 C21 P20 113.95(13) . . ?
N23 C22 C27 109.39(15) . . ?
N23 C22 C21 108.79(15) . . ?
C27 C22 C21 114.72(15) . . ?
N23 C24 C25 110.65(17) . . ?
C24 C25 C26 111.65(16) . . ?
C27 C26 C25 110.33(16) . . ?
C26 C27 C22 112.41(16) . . ?
O29 C29 N28 123.64(17) . . ?
O29 C29 C30 120.94(18) . . ?
N28 C29 C30 115.42(16) . . ?
C38 C30 C29 130.59(18) . . ?
C38 C30 S31 111.21(14) . . ?
C29 C30 S31 117.99(14) . . ?
C37 C32 C33 125.33(18) . . ?
C37 C32 S31 111.64(15) . . ?
C33 C32 S31 123.01(15) . . ?
C32 C33 C34 109.48(17) . . ?
C35 C34 C33 110.89(18) . . ?
C34 C35 C36 111.22(18) . . ?
C37 C36 C35 111.01(18) . . ?
C32 C37 C38 112.68(17) . . ?
C32 C37 C36 121.96(18) . . ?
C38 C37 C36 125.36(18) . . ?
C30 C38 C37 112.54(18) . . ?
O20A C21A C22A 109.91(18) . . ?
O20B C21B C22B 108.62(19) . . ?
O23C C23C O24C 124.51(17) . . ?
O23C C23C N23 123.79(18) . . ?
O24C C23C N23 111.71(16) . . ?
O24C C25C C26C 111.12(17) . . ?
O24C C25C C28C 110.56(16) . . ?
C26C C25C C28C 112.36(18) . . ?
O24C C25C C27C 101.80(16) . . ?
C26C C25C C27C 110.36(17) . . ?
C28C C25C C27C 110.15(19) . . ?

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
O1 P1 O1A C2A 162.99(19) . . . . ?
O1E P1 O1A C2A 34.3(4) . . . . ?
O1B P1 O1A C2A 37.7(2) . . . . ?
C2 P1 O1A C2A -71.0(2) . . . . ?
O1 P1 O1B C2B -30.6(3) . . . . ?
O1A P1 O1B C2B 93.4(2) . . . . ?
C2 P1 O1B C2B -154.4(2) . . . . ?
O1 P1 O1E C2E -49.0(12) . . . . ?
O1A P1 O1E C2E 65.7(10) . . . . ?
C2 P1 O1E C2E 172.4(9) . . . . ?
C10 N9 C2 C3 -116.38(19) . . . . ?
C10 N9 C2 P1 117.62(17) . . . . ?
O1 P1 C2 N9 93.61(15) . . . . ?
O1A P1 C2 N9 -28.78(15) . . . . ?
O1E P1 C2 N9 -122.7(5) . . . . ?
O1B P1 C2 N9 -144.92(15) . . . . ?
O1 P1 C2 C3 -30.97(16) . . . . ?
O1A P1 C2 C3 -153.36(13) . . . . ?
O1E P1 C2 C3 112.7(5) . . . . ?
O1B P1 C2 C3 90.50(16) . . . . ?
C4C N4 C3 C8 129.50(19) . . . . ?
C5 N4 C3 C8 -53.2(2) . . . . ?
C4C N4 C3 C2 -104.1(2) . . . . ?
C5 N4 C3 C2 73.2(2) . . . . ?
N9 C2 C3 N4 63.40(19) . . . . ?
P1 C2 C3 N4 -172.23(12) . . . . ?
N9 C2 C3 C8 -174.25(16) . . . . ?
P1 C2 C3 C8 -49.9(2) . . . . ?
C4C N4 C5 C6 -128.2(2) . . . . ?
C3 N4 C5 C6 54.3(2) . . . . ?
N4 C5 C6 C7 -53.0(2) . . . . ?
C5 C6 C7 C8 55.0(2) . . . . ?
C6 C7 C8 C3 -56.5(2) . . . . ?
N4 C3 C8 C7 53.4(2) . . . . ?
C2 C3 C8 C7 -69.8(2) . . . . ?
C2 N9 C10 O10 -1.0(3) . . . . ?
C2 N9 C10 C11 177.50(16) . . . . ?
O10 C10 C11 C19 -174.1(2) . . . . ?
N9 C10 C11 C19 7.3(3) . . . . ?
O10 C10 C11 S12 12.0(3) . . . . ?
N9 C10 C11 S12 -166.54(14) . . . . ?
C13 S12 C11 C19 -2.07(16) . . . . ?
C13 S12 C11 C10 172.99(15) . . . . ?
C11 S12 C13 C18 2.12(17) . . . . ?
C11 S12 C13 C14 -175.43(18) . . . . ?
C18 C13 C14 C15 -13.8(3) . . . . ?
S12 C13 C14 C15 163.37(16) . . . . ?
C13 C14 C15 C16 46.9(2) . . . . ?
C14 C15 C16 C17 -66.2(3) . . . . ?
C15 C16 C17 C18 46.6(3) . . . . ?
C14 C13 C18 C19 175.82(19) . . . . ?
S12 C13 C18 C19 -1.7(2) . . . . ?
C14 C13 C18 C17 -3.0(4) . . . . ?
S12 C13 C18 C17 179.5(2) . . . . ?
C16 C17 C18 C13 -13.4(4) . . . . ?
C16 C17 C18 C19 168.0(2) . . . . ?
C10 C11 C19 C18 -172.6(2) . . . . ?
S12 C11 C19 C18 1.5(2) . . . . ?
C13 C18 C19 C11 0.1(3) . . . . ?
C17 C18 C19 C11 178.9(2) . . . . ?
P1 O1A C2A C3A 178.9(2) . . . . ?
P1 O1B C2B C3B -85.9(3) . . . . ?
P1 O1E C2E C3E 92.3(12) . . . . ?
C6C O5C C4C O4C -6.7(3) . . . . ?
C6C O5C C4C N4 173.90(17) . . . . ?
C5 N4 C4C O4C 5.4(3) . . . . ?
C3 N4 C4C O4C -177.28(19) . . . . ?
C5 N4 C4C O5C -175.18(17) . . . . ?
C3 N4 C4C O5C 2.1(3) . . . . ?
C4C O5C C6C C8C -173.6(2) . . . . ?
C4C O5C C6C C9C -57.0(3) . . . . ?
C4C O5C C6C C7C 66.8(3) . . . . ?
O20 P20 O20A C21A 33.18(17) . . . . ?
O20B P20 O20A C21A 160.24(15) . . . . ?
C21 P20 O20A C21A -95.32(16) . . . . ?
O20 P20 O20B C21B 51.63(18) . . . . ?
O20A P20 O20B C21B -73.61(17) . . . . ?
C21 P20 O20B C21B 177.06(16) . . . . ?
C29 N28 C21 C22 111.09(18) . . . . ?
C29 N28 C21 P20 -123.12(16) . . . . ?
O20 P20 C21 N28 -87.13(14) . . . . ?
O20B P20 C21 N28 146.68(12) . . . . ?
O20A P20 C21 N28 40.37(14) . . . . ?
O20 P20 C21 C22 36.13(15) . . . . ?
O20B P20 C21 C22 -90.06(13) . . . . ?
O20A P20 C21 C22 163.63(12) . . . . ?
C23C N23 C22 C27 -136.75(17) . . . . ?
C24 N23 C22 C27 53.6(2) . . . . ?
C23C N23 C22 C21 97.23(19) . . . . ?
C24 N23 C22 C21 -72.4(2) . . . . ?
N28 C21 C22 N23 -59.78(18) . . . . ?
P20 C21 C22 N23 176.92(11) . . . . ?
N28 C21 C22 C27 177.35(15) . . . . ?
P20 C21 C22 C27 54.05(19) . . . . ?
C23C N23 C24 C25 137.50(18) . . . . ?
C22 N23 C24 C25 -53.6(2) . . . . ?
N23 C24 C25 C26 51.9(2) . . . . ?
C24 C25 C26 C27 -53.7(2) . . . . ?
C25 C26 C27 C22 54.9(2) . . . . ?
N23 C22 C27 C26 -53.1(2) . . . . ?
C21 C22 C27 C26 69.5(2) . . . . ?
C21 N28 C29 O29 8.6(3) . . . . ?
C21 N28 C29 C30 -170.92(15) . . . . ?
O29 C29 C30 C38 -179.59(19) . . . . ?
N28 C29 C30 C38 0.0(3) . . . . ?
O29 C29 C30 S31 -5.3(2) . . . . ?
N28 C29 C30 S31 174.23(13) . . . . ?
C32 S31 C30 C38 1.04(15) . . . . ?
C32 S31 C30 C29 -174.30(14) . . . . ?
C30 S31 C32 C37 -1.15(15) . . . . ?
C30 S31 C32 C33 -179.73(17) . . . . ?
C37 C32 C33 C34 16.5(3) . . . . ?
S31 C32 C33 C34 -165.10(15) . . . . ?
C32 C33 C34 C35 -47.0(2) . . . . ?
C33 C34 C35 C36 64.5(2) . . . . ?
C34 C35 C36 C37 -46.0(3) . . . . ?
C33 C32 C37 C38 179.51(18) . . . . ?
S31 C32 C37 C38 1.0(2) . . . . ?
C33 C32 C37 C36 -0.4(3) . . . . ?
S31 C32 C37 C36 -178.99(16) . . . . ?
C35 C36 C37 C32 15.0(3) . . . . ?
C35 C36 C37 C38 -164.90(19) . . . . ?
C29 C30 C38 C37 173.90(18) . . . . ?
S31 C30 C38 C37 -0.7(2) . . . . ?
C32 C37 C38 C30 -0.2(2) . . . . ?
C36 C37 C38 C30 179.77(19) . . . . ?
P20 O20A C21A C22A 133.27(16) . . . . ?
P20 O20B C21B C22B -125.3(2) . . . . ?
C25C O24C C23C O23C -1.2(3) . . . . ?
C25C O24C C23C N23 179.11(16) . . . . ?
C24 N23 C23C O23C 173.15(18) . . . . ?
C22 N23 C23C O23C 4.3(3) . . . . ?
C24 N23 C23C O24C -7.2(3) . . . . ?
C22 N23 C23C O24C -176.02(15) . . . . ?
C23C O24C C25C C26C 62.5(2) . . . . ?
C23C O24C C25C C28C -63.0(2) . . . . ?
C23C O24C C25C C27C -179.98(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N9 H9 O20 0.884(16) 2.114(18) 2.951(2) 158(2) . yes
N28 H28 O1 0.905(16) 2.024(18) 2.875(2) 156(2) . yes

_refine_diff_density_max         0.702
_refine_diff_density_min         -0.841
_refine_diff_density_rms         0.063

####################################################################### 
# 
# 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_4h-2
_database_code_depnum_ccdc_archive 'CCDC 2203666'
loop_
_audit_author_name
_audit_author_address
'Arto Valkonen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2022-08-26 deposited with the CCDC.	2023-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C24 H35 N2 O6 P S), 0.5(C6 H12)'
_chemical_formula_sum            'C51 H76 N4 O12 P2 S2'
_chemical_formula_weight         1063.21

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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

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

_cell_length_a                   48.4808(11)
_cell_length_b                   12.1659(6)
_cell_length_c                   18.9571(5)
_cell_angle_alpha                90
_cell_angle_beta                 96.648(2)
_cell_angle_gamma                90
_cell_volume                     11106.0(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4490
_cell_measurement_theta_min      3.6340
_cell_measurement_theta_max      72.4070

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_F_000             4544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.110
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    1.921
_shelx_estimated_absorpt_T_min   0.816
_shelx_estimated_absorpt_T_max   0.877
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.926
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_reflns_number            19805
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_limit_h_min       -59
_diffrn_reflns_limit_h_max       57
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.672
_diffrn_reflns_theta_max         73.417
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.956
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.956
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.956
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             10670
_reflns_number_gt                7242
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    SHELXL-2018/3
_computing_publication_material  SHELXL-2018/3
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0903P)²+16.2451P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10670
_refine_ls_number_parameters     738
_refine_ls_number_restraints     274
_refine_ls_R_factor_all          0.1001
_refine_ls_R_factor_gt           0.0687
_refine_ls_wR_factor_ref         0.2005
_refine_ls_wR_factor_gt          0.1777
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S13 S 0.61463(2) 0.62321(12) 1.01445(4) 0.0659(3) Uani 1 1 d . . . . .
P1 P 0.59459(2) 0.82855(10) 0.67463(4) 0.0533(3) Uani 1 1 d . . . . .
O1 O 0.62172(5) 0.7889(3) 0.66083(15) 0.0750(10) Uani 1 1 d . . . . .
O10 O 0.54209(5) 0.7138(3) 0.82091(12) 0.0687(9) Uani 1 1 d . . . . .
O1A O 0.59488(6) 0.9245(3) 0.72973(14) 0.0695(8) Uani 1 1 d D U . . .
O1B O 0.57480(6) 0.8735(3) 0.60944(13) 0.0672(8) Uani 1 1 d D U . . .
O4C O 0.58934(4) 0.4510(3) 0.75949(11) 0.0533(7) Uani 1 1 d . . . . .
O5C O 0.54472(4) 0.4034(2) 0.77046(11) 0.0507(7) Uani 1 1 d . . . . .
N4 N 0.55316(5) 0.5374(3) 0.69512(12) 0.0407(7) Uani 1 1 d . . . . .
N9 N 0.58403(5) 0.7037(3) 0.78111(13) 0.0477(8) Uani 1 1 d D . . . .
H9 H 0.6019(5) 0.685(3) 0.793(2) 0.057 Uiso 1 1 d D U . . .
C2 C 0.57314(6) 0.7221(3) 0.70728(15) 0.0447(8) Uani 1 1 d . . . . .
H2 H 0.553814 0.751298 0.706097 0.054 Uiso 1 1 calc R U . . .
C3 C 0.57188(6) 0.6144(3) 0.66471(15) 0.0412(8) Uani 1 1 d . . . . .
H3 H 0.590893 0.581384 0.671035 0.049 Uiso 1 1 calc R U . . .
C5 C 0.52317(6) 0.5572(3) 0.67947(15) 0.0425(8) Uani 1 1 d . . . . .
H5A H 0.518225 0.626320 0.702549 0.051 Uiso 1 1 calc R U . . .
H5B H 0.512805 0.496361 0.698972 0.051 Uiso 1 1 calc R U . . .
C6 C 0.51493(6) 0.5655(3) 0.59926(15) 0.0456(8) Uani 1 1 d . . . . .
H6A H 0.517834 0.493585 0.576777 0.055 Uiso 1 1 calc R U . . .
H6B H 0.494993 0.584493 0.589607 0.055 Uiso 1 1 calc R U . . .
C7 C 0.53231(7) 0.6531(3) 0.56771(16) 0.0468(8) Uani 1 1 d . . . . .
H7A H 0.528504 0.725883 0.587826 0.056 Uiso 1 1 calc R U . . .
H7B H 0.527336 0.656418 0.515607 0.056 Uiso 1 1 calc R U . . .
C8 C 0.56310(7) 0.6252(3) 0.58471(15) 0.0452(8) Uani 1 1 d . . . . .
H8A H 0.574316 0.683400 0.565272 0.054 Uiso 1 1 calc R U . . .
H8B H 0.566969 0.555141 0.561138 0.054 Uiso 1 1 calc R U . . .
C10 C 0.56718(7) 0.7031(4) 0.83355(16) 0.0532(10) Uani 1 1 d . . . . .
C11 C 0.58071(7) 0.6843(4) 0.90706(15) 0.0480(9) Uani 1 1 d . . . . .
C12 C 0.60597(7) 0.6399(4) 0.92463(18) 0.0590(11) Uani 1 1 d . . . . .
H12 H 0.617941 0.619677 0.890508 0.071 Uiso 1 1 calc R U . . .
C14 C 0.58338(7) 0.6807(4) 1.03201(16) 0.0499(9) Uani 1 1 d . . . . .
C15 C 0.57433(8) 0.6970(4) 1.09866(17) 0.0590(11) Uani 1 1 d . . . . .
H15 H 0.585700 0.676818 1.140864 0.071 Uiso 1 1 calc R U . . .
C16 C 0.54872(8) 0.7428(4) 1.10163(17) 0.0620(12) Uani 1 1 d . . . . .
H16 H 0.542189 0.754070 1.146428 0.074 Uiso 1 1 calc R U . . .
C17 C 0.53207(8) 0.7731(4) 1.03980(18) 0.0576(10) Uani 1 1 d . . . . .
H17 H 0.514427 0.805414 1.043097 0.069 Uiso 1 1 calc R U . . .
C18 C 0.54086(7) 0.7569(4) 0.97362(17) 0.0506(9) Uani 1 1 d . . . . .
H18 H 0.529346 0.777667 0.931764 0.061 Uiso 1 1 calc R U . . .
C19 C 0.56687(7) 0.7094(3) 0.96913(15) 0.0456(8) Uani 1 1 d . . . . .
C2A C 0.61989(18) 0.9341(10) 0.7856(5) 0.067(2) Uani 0.55 1 d D U P A 1
H2A H 0.629454 0.862240 0.791752 0.081 Uiso 0.55 1 calc R U P A 1
H2B H 0.633162 0.988449 0.770199 0.081 Uiso 0.55 1 calc R U P A 1
C3A C 0.6109(2) 0.9680(12) 0.8514(5) 0.061(2) Uani 0.55 1 d D U P A 1
H3A H 0.627055 0.974260 0.887474 0.091 Uiso 0.55 1 calc R U P A 1
H3B H 0.601656 1.039513 0.845166 0.091 Uiso 0.55 1 calc R U P A 1
H3C H 0.597957 0.913618 0.866665 0.091 Uiso 0.55 1 calc R U P A 1
C2D C 0.6160(3) 0.9885(12) 0.7675(6) 0.074(3) Uani 0.45 1 d D U P A 2
H2E H 0.633688 0.977748 0.747213 0.089 Uiso 0.45 1 calc R U P A 2
H2F H 0.610973 1.067372 0.763513 0.089 Uiso 0.45 1 calc R U P A 2
C3D C 0.6189(4) 0.957(2) 0.8385(9) 0.105(5) Uani 0.45 1 d D U P A 2
H3G H 0.633548 1.000708 0.865127 0.157 Uiso 0.45 1 calc R U P A 2
H3H H 0.601374 0.968052 0.858338 0.157 Uiso 0.45 1 calc R U P A 2
H3I H 0.624023 0.878687 0.842085 0.157 Uiso 0.45 1 calc R U P A 2
C2B C 0.5800(2) 0.9565(9) 0.5575(4) 0.071(2) Uani 0.6 1 d D U P B 1
H2C H 0.598924 0.945698 0.543625 0.085 Uiso 0.6 1 calc R U P B 1
H2D H 0.579398 1.030126 0.579477 0.085 Uiso 0.6 1 calc R U P B 1
C3B C 0.5599(2) 0.9520(8) 0.4945(4) 0.075(2) Uani 0.6 1 d D U P B 1
H3D H 0.564239 1.009163 0.461002 0.113 Uiso 0.6 1 calc R U P B 1
H3E H 0.560773 0.879691 0.472019 0.113 Uiso 0.6 1 calc R U P B 1
H3F H 0.541251 0.964104 0.507865 0.113 Uiso 0.6 1 calc R U P B 1
C2E C 0.5875(4) 0.9702(13) 0.5799(7) 0.080(3) Uani 0.4 1 d D U P B 2
H2G H 0.579882 1.038572 0.598239 0.096 Uiso 0.4 1 calc R U P B 2
H2H H 0.607876 0.969658 0.593037 0.096 Uiso 0.4 1 calc R U P B 2
C3E C 0.5810(4) 0.9640(15) 0.5038(7) 0.099(4) Uani 0.4 1 d D U P B 2
H3J H 0.589117 1.027282 0.481728 0.149 Uiso 0.4 1 calc R U P B 2
H3K H 0.588661 0.895962 0.486370 0.149 Uiso 0.4 1 calc R U P B 2
H3L H 0.560799 0.964548 0.491547 0.149 Uiso 0.4 1 calc R U P B 2
C4C C 0.56447(6) 0.4640(4) 0.74355(14) 0.0462(9) Uani 1 1 d . . . . .
C6C C 0.55252(7) 0.3299(4) 0.83086(16) 0.0496(9) Uani 1 1 d . . . . .
C7C C 0.56517(8) 0.3961(4) 0.89399(16) 0.0552(10) Uani 1 1 d . . . . .
H7C H 0.570347 0.346671 0.934186 0.083 Uiso 1 1 calc R U . . .
H7D H 0.581739 0.434372 0.881690 0.083 Uiso 1 1 calc R U . . .
H7E H 0.551619 0.449979 0.907011 0.083 Uiso 1 1 calc R U . . .
C8C C 0.52464(8) 0.2849(4) 0.8458(2) 0.0607(11) Uani 1 1 d . . . . .
H8C H 0.527336 0.233766 0.885991 0.091 Uiso 1 1 calc R U . . .
H8D H 0.512672 0.345615 0.857432 0.091 Uiso 1 1 calc R U . . .
H8E H 0.515880 0.246133 0.803754 0.091 Uiso 1 1 calc R U . . .
C9C C 0.57162(8) 0.2390(4) 0.81088(19) 0.0594(11) Uani 1 1 d . . . . .
H9A H 0.576528 0.191166 0.851994 0.089 Uiso 1 1 calc R U . . .
H9B H 0.562135 0.195835 0.771701 0.089 Uiso 1 1 calc R U . . .
H9C H 0.588538 0.271455 0.796045 0.089 Uiso 1 1 calc R U . . .
S32 S 0.63352(2) 0.71166(16) 0.44800(6) 0.0934(5) Uani 1 1 d . . . . .
P20 P 0.67772(2) 0.64305(11) 0.80167(6) 0.0629(3) Uani 1 1 d . . . . .
O20 O 0.65036(7) 0.6831(3) 0.8157(2) 0.0905(12) Uani 1 1 d . . . . .
O29 O 0.71549(5) 0.6593(2) 0.62067(12) 0.0488(6) Uani 1 1 d . . . . .
O20A O 0.67656(5) 0.5287(3) 0.76467(18) 0.0673(8) Uani 1 1 d D U . . .
O20B O 0.70008(8) 0.6232(3) 0.86709(17) 0.0882(11) Uani 1 1 d . U . . .
O23C O 0.66876(6) 0.9935(3) 0.6871(2) 0.0953(13) Uani 1 1 d . . . . .
O24C O 0.70304(6) 1.0198(2) 0.61747(13) 0.0608(7) Uani 1 1 d . . . . .
N23 N 0.71129(6) 0.9173(3) 0.71484(14) 0.0460(7) Uani 1 1 d . . . . .
N28 N 0.67988(6) 0.7283(3) 0.67472(15) 0.0503(8) Uani 1 1 d D . . . .
H28 H 0.6623(5) 0.755(3) 0.668(2) 0.060 Uiso 1 1 d D U . . .
C21 C 0.69590(7) 0.7312(3) 0.74482(17) 0.0457(8) Uani 1 1 d . . . . .
H21 H 0.714362 0.696735 0.740472 0.055 Uiso 1 1 calc R U . . .
C22 C 0.70123(8) 0.8505(3) 0.77112(18) 0.0496(9) Uani 1 1 d . . . . .
H22 H 0.683263 0.882291 0.782631 0.059 Uiso 1 1 calc R U . . .
C24 C 0.73976(7) 0.8998(4) 0.7004(2) 0.0544(9) Uani 1 1 d . . . . .
H24A H 0.744497 0.953851 0.664734 0.065 Uiso 1 1 calc R U . . .
H24B H 0.741494 0.825293 0.680364 0.065 Uiso 1 1 calc R U . . .
C25 C 0.75992(10) 0.9113(5) 0.7671(3) 0.0805(15) Uani 1 1 d . . . . .
H25A H 0.778926 0.893792 0.756287 0.097 Uiso 1 1 calc R U . . .
H25B H 0.759817 0.988148 0.784205 0.097 Uiso 1 1 calc R U . . .
C26 C 0.75201(12) 0.8349(5) 0.8241(3) 0.0927(18) Uani 1 1 d . . . . .
H26A H 0.753604 0.757658 0.808698 0.111 Uiso 1 1 calc R U . . .
H26B H 0.764762 0.845746 0.868245 0.111 Uiso 1 1 calc R U . . .
C27 C 0.72259(13) 0.8584(4) 0.83790(19) 0.0801(16) Uani 1 1 d . . . . .
H27A H 0.721785 0.933200 0.858131 0.096 Uiso 1 1 calc R U . . .
H27B H 0.717315 0.805739 0.873831 0.096 Uiso 1 1 calc R U . . .
C29 C 0.69187(7) 0.6965(3) 0.61686(18) 0.0456(8) Uani 1 1 d . . . . .
C30 C 0.67453(7) 0.7098(4) 0.54740(18) 0.0512(9) Uani 1 1 d . . . . .
C31 C 0.64722(8) 0.6871(5) 0.5345(2) 0.0681(13) Uani 1 1 d . . . . .
H31 H 0.636534 0.660120 0.569735 0.082 Uiso 1 1 calc R U . . .
C33 C 0.66541(8) 0.7582(5) 0.4265(2) 0.0696(13) Uani 1 1 d . . . . .
C34 C 0.67145(10) 0.7989(6) 0.3609(2) 0.0896(18) Uani 1 1 d . . . . .
H34 H 0.657393 0.803758 0.321722 0.107 Uiso 1 1 calc R U . . .
C35 C 0.69798(10) 0.8314(5) 0.3546(2) 0.0801(15) Uani 1 1 d . . . . .
H35 H 0.702430 0.859195 0.310425 0.096 Uiso 1 1 calc R U . . .
C36 C 0.71857(8) 0.8243(4) 0.4117(2) 0.0610(11) Uani 1 1 d . . . . .
H36 H 0.736919 0.846978 0.405871 0.073 Uiso 1 1 calc R U . . .
C37 C 0.71297(7) 0.7853(3) 0.47658(19) 0.0488(8) Uani 1 1 d . . . . .
H37 H 0.727229 0.782028 0.515371 0.059 Uiso 1 1 calc R U . . .
C38 C 0.68598(7) 0.7505(4) 0.48481(19) 0.0509(9) Uani 1 1 d . . . . .
C21A C 0.65307(17) 0.4853(8) 0.7087(7) 0.069(3) Uani 0.558(14) 1 d D U P C 1
H21A H 0.636189 0.531109 0.708691 0.083 Uiso 0.558(14) 1 calc R U P C 1
H21B H 0.659110 0.487026 0.660617 0.083 Uiso 0.558(14) 1 calc R U P C 1
C22A C 0.64745(17) 0.3717(8) 0.7295(7) 0.077(3) Uani 0.558(14) 1 d D U P C 1
H22A H 0.632693 0.340458 0.695707 0.116 Uiso 0.558(14) 1 calc R U P C 1
H22B H 0.664349 0.327555 0.729406 0.116 Uiso 0.558(14) 1 calc R U P C 1
H22C H 0.641546 0.371413 0.777234 0.116 Uiso 0.558(14) 1 calc R U P C 1
C21D C 0.64914(18) 0.4879(10) 0.7474(6) 0.062(3) Uani 0.442(14) 1 d D . P C 2
H21C H 0.635849 0.547244 0.731875 0.074 Uiso 0.442(14) 1 calc R U P C 2
H21D H 0.642562 0.447410 0.787602 0.074 Uiso 0.442(14) 1 calc R U P C 2
C22D C 0.6538(3) 0.4151(14) 0.6894(6) 0.073(4) Uani 0.442(14) 1 d D . P C 2
H22D H 0.636300 0.379511 0.671078 0.110 Uiso 0.442(14) 1 calc R U P C 2
H22E H 0.660825 0.457693 0.651358 0.110 Uiso 0.442(14) 1 calc R U P C 2
H22F H 0.667465 0.358942 0.706481 0.110 Uiso 0.442(14) 1 calc R U P C 2
C21B C 0.69384(15) 0.5446(7) 0.9221(4) 0.124(2) Uani 1 1 d D U . . .
H21E H 0.676650 0.567257 0.941637 0.149 Uiso 1 1 calc R U . . .
H21F H 0.690732 0.470692 0.900745 0.149 Uiso 1 1 calc R U . . .
C22B C 0.71588(17) 0.5402(6) 0.9769(3) 0.122(3) Uani 1 1 d D U . . .
H22G H 0.711442 0.487574 1.013078 0.183 Uiso 1 1 calc R U . . .
H22H H 0.732826 0.516759 0.957562 0.183 Uiso 1 1 calc R U . . .
H22I H 0.718768 0.613162 0.998386 0.183 Uiso 1 1 calc R U . . .
C23C C 0.69216(8) 0.9792(3) 0.6735(2) 0.0539(9) Uani 1 1 d . . . . .
C25C C 0.68593(12) 1.0942(4) 0.5690(2) 0.0859(15) Uani 1 1 d D U . . .
C26C C 0.6741(4) 1.1940(14) 0.5998(11) 0.077(5) Uani 0.47(2) 1 d D U P D 1
H26C H 0.663313 1.235745 0.561970 0.115 Uiso 0.47(2) 1 calc R U P D 1
H26D H 0.662092 1.172023 0.635396 0.115 Uiso 0.47(2) 1 calc R U P D 1
H26E H 0.689293 1.239983 0.622235 0.115 Uiso 0.47(2) 1 calc R U P D 1
C27C C 0.7122(3) 1.1322(13) 0.5291(7) 0.092(4) Uani 0.47(2) 1 d D U P D 1
H27C H 0.705958 1.185371 0.491803 0.137 Uiso 0.47(2) 1 calc R U P D 1
H27D H 0.726245 1.166196 0.563531 0.137 Uiso 0.47(2) 1 calc R U P D 1
H27E H 0.720152 1.067867 0.507829 0.137 Uiso 0.47(2) 1 calc R U P D 1
C28C C 0.6673(4) 1.0312(12) 0.5148(9) 0.100(4) Uani 0.47(2) 1 d D U P D 1
H28A H 0.656192 1.082808 0.483470 0.150 Uiso 0.47(2) 1 calc R U P D 1
H28B H 0.678519 0.985525 0.486603 0.150 Uiso 0.47(2) 1 calc R U P D 1
H28C H 0.654853 0.984221 0.538859 0.150 Uiso 0.47(2) 1 calc R U P D 1
C26F C 0.7010(4) 1.1205(13) 0.5081(6) 0.087(4) Uani 0.53(2) 1 d D U P D 2
H26F H 0.689711 1.169892 0.475669 0.131 Uiso 0.53(2) 1 calc R U P D 2
H26G H 0.718620 1.156412 0.524956 0.131 Uiso 0.53(2) 1 calc R U P D 2
H26H H 0.704699 1.052571 0.482955 0.131 Uiso 0.53(2) 1 calc R U P D 2
C27F C 0.6573(3) 1.0346(10) 0.5439(7) 0.083(4) Uani 0.53(2) 1 d D U P D 2
H27F H 0.647674 1.018028 0.585339 0.124 Uiso 0.53(2) 1 calc R U P D 2
H27G H 0.645654 1.083004 0.511519 0.124 Uiso 0.53(2) 1 calc R U P D 2
H27H H 0.660859 0.966147 0.519270 0.124 Uiso 0.53(2) 1 calc R U P D 2
C28F C 0.6800(4) 1.1931(11) 0.6141(8) 0.071(4) Uani 0.53(2) 1 d D U P D 2
H28D H 0.670013 1.169149 0.653415 0.107 Uiso 0.53(2) 1 calc R U P D 2
H28E H 0.697610 1.227556 0.633169 0.107 Uiso 0.53(2) 1 calc R U P D 2
H28F H 0.668700 1.246365 0.584763 0.107 Uiso 0.53(2) 1 calc R U P D 2
C39 C 0.50072(16) 0.9745(9) 0.8261(5) 0.151(3) Uani 1 1 d D U . . .
H39A H 0.496550 0.897607 0.838190 0.181 Uiso 0.5 1 calc R U P E 1
H39B H 0.503788 1.016586 0.870987 0.181 Uiso 0.5 1 calc R U P E 1
H39C H 0.503735 0.933113 0.871250 0.181 Uiso 0.5 1 calc R U P F 2
H39D H 0.495216 1.050532 0.836777 0.181 Uiso 0.5 1 calc R U P F 2
C40 C 0.52659(15) 0.9762(8) 0.7917(4) 0.131(2) Uani 1 1 d D U . . .
H40A H 0.533871 0.900220 0.790708 0.157 Uiso 0.5 1 calc R U P G 1
H40B H 0.540559 1.020903 0.821182 0.157 Uiso 0.5 1 calc R U P G 1
H40C H 0.541258 0.932930 0.819881 0.157 Uiso 0.5 1 calc R U P H 2
H40D H 0.533269 1.052547 0.787702 0.157 Uiso 0.5 1 calc R U P H 2
C41 C 0.5235(2) 1.0206(13) 0.7179(6) 0.110(3) Uani 0.5 1 d D U P I 1
H41A H 0.521571 1.101552 0.719751 0.132 Uiso 0.5 1 calc R U P I 1
H41B H 0.540471 1.003790 0.695584 0.132 Uiso 0.5 1 calc R U P I 1
C41D C 0.5197(3) 0.9259(14) 0.7185(7) 0.124(4) Uani 0.5 1 d D U P I 2
H41C H 0.536834 0.925606 0.694809 0.149 Uiso 0.5 1 calc R U P I 2
H41D H 0.514341 0.848250 0.724758 0.149 Uiso 0.5 1 calc R U P I 2


_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
S13 C12 1.718(3) . ?
S13 C14 1.735(4) . ?
P1 O1 1.453(3) . ?
P1 O1A 1.565(3) . ?
P1 O1B 1.572(3) . ?
P1 C2 1.814(4) . ?
O10 C10 1.220(4) . ?
O1A C2D 1.412(10) . ?
O1A C2A 1.520(8) . ?
O1B C2B 1.453(8) . ?
O1B C2E 1.469(12) . ?
O4C C4C 1.219(4) . ?
O5C C4C 1.354(4) . ?
O5C C6C 1.467(4) . ?
N4 C4C 1.350(4) . ?
N4 C3 1.468(4) . ?
N4 C5 1.470(4) . ?
N9 C10 1.358(4) . ?
N9 C2 1.455(4) . ?
C2 C3 1.536(5) . ?
C3 C8 1.533(4) . ?
C5 C6 1.530(4) . ?
C6 C7 1.524(5) . ?
C7 C8 1.528(5) . ?
C10 C11 1.487(4) . ?
C11 C12 1.345(5) . ?
C11 C19 1.453(4) . ?
C14 C15 1.399(5) . ?
C14 C19 1.401(5) . ?
C15 C16 1.368(6) . ?
C16 C17 1.393(6) . ?
C17 C18 1.385(4) . ?
C18 C19 1.398(5) . ?
C2A C3A 1.428(10) . ?
C2D C3D 1.393(14) . ?
C2B C3B 1.454(10) . ?
C2E C3E 1.442(13) . ?
C6C C7C 1.512(5) . ?
C6C C8C 1.516(5) . ?
C6C C9C 1.518(5) . ?
S32 C31 1.722(4) . ?
S32 C33 1.739(4) . ?
P20 O20 1.466(3) . ?
P20 O20A 1.556(4) . ?
P20 O20B 1.569(4) . ?
P20 C21 1.819(3) . ?
O29 C29 1.226(4) . ?
O20A C21D 1.421(8) . ?
O20A C21A 1.555(11) . ?
O20B C21B 1.471(6) . ?
O23C C23C 1.205(5) . ?
O24C C23C 1.334(4) . ?
O24C C25C 1.474(5) . ?
N23 C23C 1.369(5) . ?
N23 C24 1.454(4) . ?
N23 C22 1.468(4) . ?
N28 C29 1.356(4) . ?
N28 C21 1.460(4) . ?
C21 C22 1.547(6) . ?
C22 C27 1.543(6) . ?
C24 C25 1.511(6) . ?
C25 C26 1.508(8) . ?
C26 C27 1.507(8) . ?
C29 C30 1.487(5) . ?
C30 C31 1.347(5) . ?
C30 C38 1.454(5) . ?
C33 C34 1.400(7) . ?
C33 C38 1.404(5) . ?
C34 C35 1.364(7) . ?
C35 C36 1.388(6) . ?
C36 C37 1.374(5) . ?
C37 C38 1.401(5) . ?
C21A C22A 1.471(11) . ?
C21D C22D 1.450(12) . ?
C21B C22B 1.403(8) . ?
C25C C26F 1.472(9) . ?
C25C C26C 1.490(11) . ?
C25C C28C 1.499(10) . ?
C25C C28F 1.523(10) . ?
C25C C27F 1.590(10) . ?
C25C C27C 1.621(11) . ?
C39 C41D 1.360(11) 2_656 ?
C39 C41 1.470(12) 2_656 ?
C39 C40 1.479(8) . ?
C40 C41 1.491(11) . ?
C40 C41D 1.518(12) . ?

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
C12 S13 C14 91.38(17) . . ?
O1 P1 O1A 115.42(17) . . ?
O1 P1 O1B 117.16(17) . . ?
O1A P1 O1B 102.89(19) . . ?
O1 P1 C2 113.0(2) . . ?
O1A P1 C2 105.43(16) . . ?
O1B P1 C2 101.23(15) . . ?
C2D O1A P1 134.4(6) . . ?
C2A O1A P1 117.9(4) . . ?
C2B O1B P1 129.4(4) . . ?
C2E O1B P1 109.5(7) . . ?
C4C O5C C6C 119.7(2) . . ?
C4C N4 C3 117.9(3) . . ?
C4C N4 C5 124.1(3) . . ?
C3 N4 C5 117.2(3) . . ?
C10 N9 C2 121.5(3) . . ?
N9 C2 C3 111.2(3) . . ?
N9 C2 P1 106.2(2) . . ?
C3 C2 P1 114.8(2) . . ?
N4 C3 C8 109.2(3) . . ?
N4 C3 C2 109.1(2) . . ?
C8 C3 C2 115.9(3) . . ?
N4 C5 C6 110.5(2) . . ?
C7 C6 C5 110.1(3) . . ?
C6 C7 C8 109.4(3) . . ?
C7 C8 C3 112.4(2) . . ?
O10 C10 N9 121.8(3) . . ?
O10 C10 C11 121.5(3) . . ?
N9 C10 C11 116.7(3) . . ?
C12 C11 C19 112.1(3) . . ?
C12 C11 C10 125.7(3) . . ?
C19 C11 C10 122.1(3) . . ?
C11 C12 S13 113.8(2) . . ?
C15 C14 C19 121.7(3) . . ?
C15 C14 S13 127.1(3) . . ?
C19 C14 S13 111.3(2) . . ?
C16 C15 C14 118.4(3) . . ?
C15 C16 C17 120.9(3) . . ?
C18 C17 C16 121.0(4) . . ?
C17 C18 C19 119.2(3) . . ?
C18 C19 C14 118.8(3) . . ?
C18 C19 C11 129.8(3) . . ?
C14 C19 C11 111.4(3) . . ?
C3A C2A O1A 109.4(8) . . ?
C3D C2D O1A 108.9(14) . . ?
O1B C2B C3B 112.2(7) . . ?
C3E C2E O1B 106.7(12) . . ?
O4C C4C N4 124.5(3) . . ?
O4C C4C O5C 123.9(3) . . ?
N4 C4C O5C 111.5(3) . . ?
O5C C6C C7C 109.7(3) . . ?
O5C C6C C8C 102.2(3) . . ?
C7C C6C C8C 109.4(3) . . ?
O5C C6C C9C 111.0(3) . . ?
C7C C6C C9C 112.4(3) . . ?
C8C C6C C9C 111.5(4) . . ?
C31 S32 C33 91.41(19) . . ?
O20 P20 O20A 113.1(2) . . ?
O20 P20 O20B 117.7(2) . . ?
O20A P20 O20B 101.8(2) . . ?
O20 P20 C21 115.02(19) . . ?
O20A P20 C21 104.75(17) . . ?
O20B P20 C21 102.78(16) . . ?
C21D O20A P20 113.6(5) . . ?
C21A O20A P20 126.6(4) . . ?
C21B O20B P20 118.7(4) . . ?
C23C O24C C25C 118.5(4) . . ?
C23C N23 C24 124.6(3) . . ?
C23C N23 C22 117.4(3) . . ?
C24 N23 C22 117.2(3) . . ?
C29 N28 C21 120.7(3) . . ?
N28 C21 C22 111.5(3) . . ?
N28 C21 P20 106.4(2) . . ?
C22 C21 P20 115.9(2) . . ?
N23 C22 C27 108.3(3) . . ?
N23 C22 C21 110.0(3) . . ?
C27 C22 C21 113.2(3) . . ?
N23 C24 C25 111.5(3) . . ?
C26 C25 C24 110.4(4) . . ?
C27 C26 C25 109.4(4) . . ?
C26 C27 C22 113.9(3) . . ?
O29 C29 N28 122.9(3) . . ?
O29 C29 C30 121.4(3) . . ?
N28 C29 C30 115.7(3) . . ?
C31 C30 C38 112.4(3) . . ?
C31 C30 C29 125.6(3) . . ?
C38 C30 C29 122.0(3) . . ?
C30 C31 S32 113.6(3) . . ?
C34 C33 C38 121.4(4) . . ?
C34 C33 S32 127.3(3) . . ?
C38 C33 S32 111.3(3) . . ?
C35 C34 C33 118.5(4) . . ?
C34 C35 C36 120.9(4) . . ?
C37 C36 C35 121.4(4) . . ?
C36 C37 C38 119.2(3) . . ?
C37 C38 C33 118.6(3) . . ?
C37 C38 C30 130.1(3) . . ?
C33 C38 C30 111.2(3) . . ?
C22A C21A O20A 106.3(8) . . ?
O20A C21D C22D 99.4(8) . . ?
C22B C21B O20B 110.4(5) . . ?
O23C C23C O24C 125.8(4) . . ?
O23C C23C N23 123.3(3) . . ?
O24C C23C N23 110.9(3) . . ?
C26F C25C O24C 109.2(7) . . ?
O24C C25C C26C 118.0(9) . . ?
O24C C25C C28C 111.4(7) . . ?
C26C C25C C28C 117.2(9) . . ?
C26F C25C C28F 114.3(8) . . ?
O24C C25C C28F 105.3(7) . . ?
C26F C25C C27F 111.1(6) . . ?
O24C C25C C27F 108.4(5) . . ?
C28F C25C C27F 108.3(8) . . ?
O24C C25C C27C 92.9(7) . . ?
C26C C25C C27C 107.9(9) . . ?
C28C C25C C27C 105.7(7) . . ?
C41D C39 C40 109.0(9) 2_656 . ?
C41 C39 C40 114.0(7) 2_656 . ?
C39 C40 C41 114.8(7) . . ?
C39 C40 C41D 106.8(8) . . ?
C39 C41 C40 112.4(9) 2_656 . ?
C39 C41D C40 117.4(10) 2_656 . ?

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
O1 P1 O1A C2D 4.8(9) . . . . ?
O1B P1 O1A C2D -124.1(9) . . . . ?
C2 P1 O1A C2D 130.2(9) . . . . ?
O1 P1 O1A C2A -26.3(6) . . . . ?
O1B P1 O1A C2A -155.2(5) . . . . ?
C2 P1 O1A C2A 99.1(5) . . . . ?
O1 P1 O1B C2B -52.9(7) . . . . ?
O1A P1 O1B C2B 74.8(7) . . . . ?
C2 P1 O1B C2B -176.3(7) . . . . ?
O1 P1 O1B C2E -62.8(9) . . . . ?
O1A P1 O1B C2E 65.0(9) . . . . ?
C2 P1 O1B C2E 173.9(8) . . . . ?
C10 N9 C2 C3 -104.6(4) . . . . ?
C10 N9 C2 P1 129.9(4) . . . . ?
O1 P1 C2 N9 75.4(3) . . . . ?
O1A P1 C2 N9 -51.5(3) . . . . ?
O1B P1 C2 N9 -158.4(2) . . . . ?
O1 P1 C2 C3 -47.9(3) . . . . ?
O1A P1 C2 C3 -174.9(2) . . . . ?
O1B P1 C2 C3 78.2(3) . . . . ?
C4C N4 C3 C8 137.9(3) . . . . ?
C5 N4 C3 C8 -51.8(4) . . . . ?
C4C N4 C3 C2 -94.5(3) . . . . ?
C5 N4 C3 C2 75.9(3) . . . . ?
N9 C2 C3 N4 61.3(3) . . . . ?
P1 C2 C3 N4 -178.0(2) . . . . ?
N9 C2 C3 C8 -174.9(2) . . . . ?
P1 C2 C3 C8 -54.3(3) . . . . ?
C4C N4 C5 C6 -136.4(3) . . . . ?
C3 N4 C5 C6 54.0(4) . . . . ?
N4 C5 C6 C7 -55.0(4) . . . . ?
C5 C6 C7 C8 57.6(4) . . . . ?
C6 C7 C8 C3 -57.2(4) . . . . ?
N4 C3 C8 C7 52.3(4) . . . . ?
C2 C3 C8 C7 -71.3(4) . . . . ?
C2 N9 C10 O10 2.8(7) . . . . ?
C2 N9 C10 C11 -179.5(4) . . . . ?
O10 C10 C11 C12 159.0(5) . . . . ?
N9 C10 C11 C12 -18.7(7) . . . . ?
O10 C10 C11 C19 -18.6(7) . . . . ?
N9 C10 C11 C19 163.7(4) . . . . ?
C19 C11 C12 S13 1.0(5) . . . . ?
C10 C11 C12 S13 -176.8(4) . . . . ?
C14 S13 C12 C11 -1.2(4) . . . . ?
C12 S13 C14 C15 -179.9(4) . . . . ?
C12 S13 C14 C19 1.1(3) . . . . ?
C19 C14 C15 C16 -0.4(7) . . . . ?
S13 C14 C15 C16 -179.2(4) . . . . ?
C14 C15 C16 C17 -0.4(7) . . . . ?
C15 C16 C17 C18 0.6(7) . . . . ?
C16 C17 C18 C19 -0.1(7) . . . . ?
C17 C18 C19 C14 -0.6(6) . . . . ?
C17 C18 C19 C11 -179.8(4) . . . . ?
C15 C14 C19 C18 0.8(6) . . . . ?
S13 C14 C19 C18 179.9(3) . . . . ?
C15 C14 C19 C11 -179.8(4) . . . . ?
S13 C14 C19 C11 -0.8(4) . . . . ?
C12 C11 C19 C18 179.1(4) . . . . ?
C10 C11 C19 C18 -3.0(7) . . . . ?
C12 C11 C19 C14 -0.2(5) . . . . ?
C10 C11 C19 C14 177.7(4) . . . . ?
P1 O1A C2A C3A -142.6(9) . . . . ?
P1 O1A C2D C3D -107.4(13) . . . . ?
P1 O1B C2B C3B 163.0(6) . . . . ?
P1 O1B C2E C3E 142.4(12) . . . . ?
C3 N4 C4C O4C -6.5(5) . . . . ?
C5 N4 C4C O4C -176.1(3) . . . . ?
C3 N4 C4C O5C 175.9(3) . . . . ?
C5 N4 C4C O5C 6.3(5) . . . . ?
C6C O5C C4C O4C 10.8(5) . . . . ?
C6C O5C C4C N4 -171.5(3) . . . . ?
C4C O5C C6C C7C 60.8(4) . . . . ?
C4C O5C C6C C8C 176.9(3) . . . . ?
C4C O5C C6C C9C -64.1(5) . . . . ?
O20 P20 O20A C21D 3.8(7) . . . . ?
O20B P20 O20A C21D 131.0(6) . . . . ?
C21 P20 O20A C21D -122.2(6) . . . . ?
O20 P20 O20A C21A 35.2(6) . . . . ?
O20B P20 O20A C21A 162.4(6) . . . . ?
C21 P20 O20A C21A -90.8(6) . . . . ?
O20 P20 O20B C21B 59.0(6) . . . . ?
O20A P20 O20B C21B -65.2(5) . . . . ?
C21 P20 O20B C21B -173.5(5) . . . . ?
C29 N28 C21 C22 109.7(4) . . . . ?
C29 N28 C21 P20 -123.0(3) . . . . ?
O20 P20 C21 N28 -66.8(3) . . . . ?
O20A P20 C21 N28 58.1(3) . . . . ?
O20B P20 C21 N28 164.1(3) . . . . ?
O20 P20 C21 C22 57.8(3) . . . . ?
O20A P20 C21 C22 -177.3(3) . . . . ?
O20B P20 C21 C22 -71.3(3) . . . . ?
C23C N23 C22 C27 -139.1(4) . . . . ?
C24 N23 C22 C27 50.0(4) . . . . ?
C23C N23 C22 C21 96.7(4) . . . . ?
C24 N23 C22 C21 -74.2(4) . . . . ?
N28 C21 C22 N23 -47.8(4) . . . . ?
P20 C21 C22 N23 -169.7(2) . . . . ?
N28 C21 C22 C27 -169.1(3) . . . . ?
P20 C21 C22 C27 69.0(4) . . . . ?
C23C N23 C24 C25 135.9(4) . . . . ?
C22 N23 C24 C25 -54.0(5) . . . . ?
N23 C24 C25 C26 55.3(6) . . . . ?
C24 C25 C26 C27 -56.6(6) . . . . ?
C25 C26 C27 C22 56.0(5) . . . . ?
N23 C22 C27 C26 -50.8(5) . . . . ?
C21 C22 C27 C26 71.5(5) . . . . ?
C21 N28 C29 O29 6.9(6) . . . . ?
C21 N28 C29 C30 -172.9(3) . . . . ?
O29 C29 C30 C31 139.0(5) . . . . ?
N28 C29 C30 C31 -41.2(6) . . . . ?
O29 C29 C30 C38 -41.2(6) . . . . ?
N28 C29 C30 C38 138.6(4) . . . . ?
C38 C30 C31 S32 0.3(6) . . . . ?
C29 C30 C31 S32 -179.9(3) . . . . ?
C33 S32 C31 C30 -1.3(4) . . . . ?
C31 S32 C33 C34 -178.1(6) . . . . ?
C31 S32 C33 C38 2.0(4) . . . . ?
C38 C33 C34 C35 0.0(9) . . . . ?
S32 C33 C34 C35 -179.9(5) . . . . ?
C33 C34 C35 C36 0.0(10) . . . . ?
C34 C35 C36 C37 -0.5(9) . . . . ?
C35 C36 C37 C38 0.9(7) . . . . ?
C36 C37 C38 C33 -0.9(7) . . . . ?
C36 C37 C38 C30 -177.8(4) . . . . ?
C34 C33 C38 C37 0.5(8) . . . . ?
S32 C33 C38 C37 -179.6(3) . . . . ?
C34 C33 C38 C30 177.9(5) . . . . ?
S32 C33 C38 C30 -2.2(5) . . . . ?
C31 C30 C38 C37 178.3(5) . . . . ?
C29 C30 C38 C37 -1.5(7) . . . . ?
C31 C30 C38 C33 1.3(6) . . . . ?
C29 C30 C38 C33 -178.6(4) . . . . ?
P20 O20A C21A C22A -135.6(7) . . . . ?
P20 O20A C21D C22D 155.3(8) . . . . ?
P20 O20B C21B C22B -178.4(5) . . . . ?
C25C O24C C23C O23C 3.6(7) . . . . ?
C25C O24C C23C N23 -176.4(3) . . . . ?
C24 N23 C23C O23C -179.1(4) . . . . ?
C22 N23 C23C O23C 10.8(6) . . . . ?
C24 N23 C23C O24C 1.0(5) . . . . ?
C22 N23 C23C O24C -169.1(3) . . . . ?
C23C O24C C25C C26F -174.8(8) . . . . ?
C23C O24C C25C C26C 55.6(11) . . . . ?
C23C O24C C25C C28C -84.3(10) . . . . ?
C23C O24C C25C C28F 62.1(9) . . . . ?
C23C O24C C25C C27F -53.7(8) . . . . ?
C23C O24C C25C C27C 167.6(6) . . . . ?
C41 C39 C40 C41 -1.9(13) 2_656 . . . ?
C41D C39 C40 C41D 2.0(11) 2_656 . . . ?
C39 C40 C41 C39 -46.6(13) . . . 2_656 ?
C39 C40 C41D C39 58.3(15) . . . 2_656 ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N9 H9 O20 0.902(19) 2.34(2) 3.217(4) 165(4) . yes
N28 H28 O1 0.908(19) 2.00(2) 2.897(4) 169(4) . yes

_refine_diff_density_max         0.539
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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_4k-1
_database_code_depnum_ccdc_archive 'CCDC 2203668'
loop_
_audit_author_name
_audit_author_address
'Arto Valkonen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2022-08-26 deposited with the CCDC.	2023-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H37 N2 O6 P S'
_chemical_formula_sum            'C25 H37 N2 O6 P S'
_chemical_formula_weight         524.59

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'
S S 0.1246 0.1234 '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'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0460(3)
_cell_length_b                   10.9706(4)
_cell_length_c                   13.8583(3)
_cell_angle_alpha                86.282(2)
_cell_angle_beta                 87.202(2)
_cell_angle_gamma                79.542(3)
_cell_volume                     1348.64(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    13016
_cell_measurement_theta_min      2.2910
_cell_measurement_theta_max      29.6710

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.292
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.220
_shelx_estimated_absorpt_T_min   0.927
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.947
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0107
_diffrn_reflns_number            32817
_diffrn_reflns_av_unetI/netI     0.0312
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.291
_diffrn_reflns_theta_max         29.921
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7198
_reflns_number_gt                6021
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    SHELXL-2018/3
_computing_publication_material  SHELXL-2018/3
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0493P)²+0.5621P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7198
_refine_ls_number_parameters     338
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1105
_refine_ls_wR_factor_gt          0.1033
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S13 S 0.80178(7) 0.96653(7) 0.14564(4) 0.02283(19) Uani 0.709(2) 1 d D . P A 1
S13D S 0.83786(19) 0.68363(19) 0.21305(12) 0.0250(4) Uani 0.291(2) 1 d D . P A
2
P1 P 0.35492(4) 0.82432(3) 0.56284(2) 0.02045(9) Uani 1 1 d . . . . .
O1 O 0.37123(12) 0.94104(9) 0.60471(7) 0.0260(2) Uani 1 1 d . . . . .
O10 O 0.52012(14) 0.67173(10) 0.30738(7) 0.0332(3) Uani 1 1 d . . . . .
O1A O 0.22109(11) 0.83856(9) 0.49200(7) 0.0251(2) Uani 1 1 d . . . . .
O1B O 0.32285(12) 0.71601(9) 0.63540(7) 0.0266(2) Uani 1 1 d . . . . .
O4C O 0.72425(14) 0.84095(10) 0.71884(7) 0.0324(3) Uani 1 1 d . . . . .
O5C O 0.67245(12) 0.67213(9) 0.80910(7) 0.0257(2) Uani 1 1 d . . . . .
N4 N 0.65630(14) 0.67862(10) 0.64788(8) 0.0221(2) Uani 1 1 d . . . . .
N9 N 0.53505(13) 0.82628(11) 0.40592(8) 0.0203(2) Uani 1 1 d D . . . .
H9 H 0.5550(18) 0.9022(13) 0.4101(12) 0.024 Uiso 1 1 d D U . . .
C2 C 0.52201(15) 0.75142(12) 0.49589(9) 0.0194(3) Uani 1 1 d . . . . .
H2 H 0.507998 0.666861 0.479646 0.023 Uiso 1 1 calc R U . . .
C3 C 0.66961(16) 0.73850(13) 0.55075(9) 0.0218(3) Uani 1 1 d . . . . .
H3 H 0.690635 0.823753 0.558084 0.026 Uiso 1 1 calc R U . . .
C5 C 0.64524(16) 0.54633(12) 0.65129(10) 0.0236(3) Uani 1 1 d . . . . .
H5A H 0.550646 0.536615 0.622067 0.028 Uiso 1 1 calc R U . . .
H5B H 0.642626 0.513589 0.719506 0.028 Uiso 1 1 calc R U . . .
C6 C 0.77854(17) 0.47270(14) 0.59675(11) 0.0287(3) Uani 1 1 d . . . . .
H6A H 0.764645 0.385448 0.594842 0.034 Uiso 1 1 calc R U . . .
H6B H 0.871795 0.473149 0.631167 0.034 Uiso 1 1 calc R U . . .
C7 C 0.79417(17) 0.52822(14) 0.49340(11) 0.0285(3) Uani 1 1 d . . . . .
H7A H 0.886314 0.483461 0.461077 0.034 Uiso 1 1 calc R U . . .
H7B H 0.706785 0.517976 0.456374 0.034 Uiso 1 1 calc R U . . .
C8 C 0.80262(16) 0.66589(14) 0.49403(10) 0.0261(3) Uani 1 1 d . . . . .
H8A H 0.804245 0.701445 0.426562 0.031 Uiso 1 1 calc R U . . .
H8B H 0.897488 0.674900 0.523255 0.031 Uiso 1 1 calc R U . . .
C10 C 0.53687(15) 0.77784(13) 0.31885(9) 0.0219(3) Uani 1 1 d . . . . .
C11 C 0.56576(16) 0.86621(14) 0.23362(9) 0.0242(3) Uani 1 1 d . . . . .
H11A H 0.502801 0.855548 0.179400 0.029 Uiso 1 1 calc R U . . .
H11B H 0.537479 0.952986 0.252790 0.029 Uiso 1 1 calc R U . . .
C12 C 0.72880(16) 0.84121(13) 0.20119(9) 0.0232(3) Uani 1 1 d D . . . .
C14 C 0.97546(16) 0.86906(14) 0.13133(10) 0.0252(3) Uani 1 1 d D . . . .
C15 C 1.10290(17) 0.90895(15) 0.08963(10) 0.0289(3) Uani 1 1 d . . . . .
H15 H 1.098776 0.992721 0.066049 0.035 Uiso 1 1 calc R U . . .
C16 C 1.23494(18) 0.82431(17) 0.08334(11) 0.0350(4) Uani 1 1 d . . . . .
H16 H 1.322480 0.849886 0.054313 0.042 Uiso 1 1 calc R U . . .
C17 C 1.2422(2) 0.70173(17) 0.11889(12) 0.0393(4) Uani 1 1 d . . . . .
H17 H 1.335021 0.645255 0.114975 0.047 Uiso 1 1 calc R U . . .
C18 C 1.1160(2) 0.66141(16) 0.15976(12) 0.0376(4) Uani 1 1 d . . . . .
H18 H 1.121112 0.577473 0.183165 0.045 Uiso 1 1 calc R U . . .
C19 C 0.98101(18) 0.74558(15) 0.16619(10) 0.0298(3) Uani 1 1 d D . . . .
C20 C 0.8285(3) 0.7390(3) 0.20716(19) 0.0264(6) Uani 0.709(2) 1 d D . P A 1
H20 H 0.804124 0.664006 0.236386 0.032 Uiso 0.709(2) 1 calc R U P A 1
C20D C 0.8219(8) 0.9106(8) 0.1596(5) 0.0394(19) Uani 0.291(2) 1 d D . P A 2
H20D H 0.782635 0.996336 0.147511 0.047 Uiso 0.291(2) 1 calc R U P A 2
C2A C 0.18020(17) 0.95124(13) 0.42956(10) 0.0264(3) Uani 1 1 d . . . . .
H2A1 H 0.271927 0.980047 0.402311 0.032 Uiso 1 1 calc R U . . .
H2A2 H 0.120413 1.018101 0.467160 0.032 Uiso 1 1 calc R U . . .
C3A C 0.0897(2) 0.92055(17) 0.34990(12) 0.0398(4) Uani 1 1 d . . . . .
H3A1 H 0.060641 0.994606 0.306818 0.060 Uiso 1 1 calc R U . . .
H3A2 H 0.149990 0.854527 0.313063 0.060 Uiso 1 1 calc R U . . .
H3A3 H -0.000933 0.892432 0.377660 0.060 Uiso 1 1 calc R U . . .
C2B C 0.2170(2) 0.73362(18) 0.71678(13) 0.0428(4) Uani 1 1 d . . . . .
H2B1 H 0.117463 0.719309 0.698364 0.051 Uiso 1 1 calc R U . . .
H2B2 H 0.205561 0.819745 0.737230 0.051 Uiso 1 1 calc R U . . .
C3B C 0.2739(2) 0.6445(2) 0.79748(14) 0.0582(6) Uani 1 1 d . . . . .
H3B1 H 0.202920 0.655599 0.853265 0.087 Uiso 1 1 calc R U . . .
H3B2 H 0.284304 0.559524 0.776857 0.087 Uiso 1 1 calc R U . . .
H3B3 H 0.372131 0.659651 0.815603 0.087 Uiso 1 1 calc R U . . .
C4C C 0.68854(16) 0.73891(13) 0.72453(10) 0.0227(3) Uani 1 1 d . . . . .
C6C C 0.70514(18) 0.72048(14) 0.90123(10) 0.0272(3) Uani 1 1 d . . . . .
C7C C 0.6610(2) 0.62458(17) 0.97564(11) 0.0400(4) Uani 1 1 d . . . . .
H7C1 H 0.678347 0.647830 1.040679 0.060 Uiso 1 1 calc R U . . .
H7C2 H 0.554235 0.620908 0.970390 0.060 Uiso 1 1 calc R U . . .
H7C3 H 0.721769 0.543055 0.963917 0.060 Uiso 1 1 calc R U . . .
C8C C 0.87203(19) 0.72324(17) 0.90315(12) 0.0368(4) Uani 1 1 d . . . . .
H8C1 H 0.894001 0.755307 0.964241 0.055 Uiso 1 1 calc R U . . .
H8C2 H 0.929357 0.639008 0.897521 0.055 Uiso 1 1 calc R U . . .
H8C3 H 0.900552 0.777200 0.848929 0.055 Uiso 1 1 calc R U . . .
C9C C 0.6089(2) 0.84676(15) 0.91686(11) 0.0348(4) Uani 1 1 d . . . . .
H9C1 H 0.633042 0.876407 0.978389 0.052 Uiso 1 1 calc R U . . .
H9C2 H 0.629291 0.905658 0.863802 0.052 Uiso 1 1 calc R U . . .
H9C3 H 0.502373 0.839703 0.918462 0.052 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S13 C14 1.7431(16) . ?
S13 C12 1.7496(15) . ?
S13D C19 1.655(2) . ?
S13D C12 1.830(2) . ?
P1 O1 1.4736(10) . ?
P1 O1B 1.5649(10) . ?
P1 O1A 1.5752(10) . ?
P1 C2 1.8181(14) . ?
O10 C10 1.2221(17) . ?
O1A C2A 1.4630(16) . ?
O1B C2B 1.4426(18) . ?
O4C C4C 1.2170(17) . ?
O5C C4C 1.3572(16) . ?
O5C C6C 1.4768(16) . ?
N4 C4C 1.3573(17) . ?
N4 C3 1.4684(16) . ?
N4 C5 1.4702(17) . ?
N9 C10 1.3479(17) . ?
N9 C2 1.4598(16) . ?
C2 C3 1.5483(18) . ?
C3 C8 1.530(2) . ?
C5 C6 1.521(2) . ?
C6 C7 1.530(2) . ?
C7 C8 1.527(2) . ?
C10 C11 1.5220(18) . ?
C11 C12 1.502(2) . ?
C12 C20 1.306(4) . ?
C12 C20D 1.322(8) . ?
C14 C15 1.393(2) . ?
C14 C19 1.401(2) . ?
C14 C20D 1.426(7) . ?
C15 C16 1.376(2) . ?
C16 C17 1.393(3) . ?
C17 C18 1.381(3) . ?
C18 C19 1.394(2) . ?
C19 C20 1.479(3) . ?
C2A C3A 1.496(2) . ?
C2B C3B 1.484(3) . ?
C6C C8C 1.517(2) . ?
C6C C7C 1.517(2) . ?
C6C C9C 1.519(2) . ?

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
C14 S13 C12 89.13(8) . . ?
C19 S13D C12 85.65(12) . . ?
O1 P1 O1B 116.87(6) . . ?
O1 P1 O1A 113.95(6) . . ?
O1B P1 O1A 102.38(6) . . ?
O1 P1 C2 113.78(6) . . ?
O1B P1 C2 102.15(6) . . ?
O1A P1 C2 106.26(6) . . ?
C2A O1A P1 121.08(9) . . ?
C2B O1B P1 123.36(10) . . ?
C4C O5C C6C 119.89(11) . . ?
C4C N4 C3 118.02(11) . . ?
C4C N4 C5 124.49(11) . . ?
C3 N4 C5 115.73(11) . . ?
C10 N9 C2 121.63(11) . . ?
N9 C2 C3 109.00(11) . . ?
N9 C2 P1 107.64(9) . . ?
C3 C2 P1 114.30(9) . . ?
N4 C3 C8 109.72(11) . . ?
N4 C3 C2 111.63(11) . . ?
C8 C3 C2 111.27(11) . . ?
N4 C5 C6 110.63(12) . . ?
C5 C6 C7 110.87(12) . . ?
C8 C7 C6 110.56(12) . . ?
C7 C8 C3 112.10(12) . . ?
O10 C10 N9 124.14(13) . . ?
O10 C10 C11 121.66(12) . . ?
N9 C10 C11 114.18(12) . . ?
C12 C11 C10 110.46(11) . . ?
C20 C12 C11 130.42(18) . . ?
C20D C12 C11 134.1(4) . . ?
C20 C12 S13 112.87(16) . . ?
C11 C12 S13 116.71(10) . . ?
C20D C12 S13D 105.7(4) . . ?
C11 C12 S13D 120.15(11) . . ?
C15 C14 C19 120.94(14) . . ?
C15 C14 C20D 143.1(4) . . ?
C19 C14 C20D 95.9(4) . . ?
C15 C14 S13 123.44(12) . . ?
C19 C14 S13 115.62(12) . . ?
C16 C15 C14 118.52(15) . . ?
C15 C16 C17 121.03(15) . . ?
C18 C17 C16 120.71(16) . . ?
C17 C18 C19 119.08(15) . . ?
C18 C19 C14 119.71(15) . . ?
C18 C19 C20 134.60(19) . . ?
C14 C19 C20 105.64(19) . . ?
C18 C19 S13D 113.93(14) . . ?
C14 C19 S13D 126.32(15) . . ?
C12 C20 C19 116.7(2) . . ?
C12 C20D C14 126.2(6) . . ?
O1A C2A C3A 107.71(12) . . ?
O1B C2B C3B 108.70(15) . . ?
O4C C4C O5C 124.03(12) . . ?
O4C C4C N4 124.61(13) . . ?
O5C C4C N4 111.34(12) . . ?
O5C C6C C8C 109.32(12) . . ?
O5C C6C C7C 102.47(12) . . ?
C8C C6C C7C 110.94(13) . . ?
O5C C6C C9C 111.32(12) . . ?
C8C C6C C9C 112.29(14) . . ?
C7C C6C C9C 110.08(13) . . ?

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
O1 P1 O1A C2A 34.94(12) . . . . ?
O1B P1 O1A C2A 162.08(10) . . . . ?
C2 P1 O1A C2A -91.16(11) . . . . ?
O1 P1 O1B C2B 43.26(15) . . . . ?
O1A P1 O1B C2B -81.99(14) . . . . ?
C2 P1 O1B C2B 168.11(13) . . . . ?
C10 N9 C2 C3 114.10(14) . . . . ?
C10 N9 C2 P1 -121.41(12) . . . . ?
O1 P1 C2 N9 -72.00(10) . . . . ?
O1B P1 C2 N9 161.12(9) . . . . ?
O1A P1 C2 N9 54.20(10) . . . . ?
O1 P1 C2 C3 49.22(11) . . . . ?
O1B P1 C2 C3 -77.65(10) . . . . ?
O1A P1 C2 C3 175.43(9) . . . . ?
C4C N4 C3 C8 110.95(14) . . . . ?
C5 N4 C3 C8 -54.66(15) . . . . ?
C4C N4 C3 C2 -125.23(13) . . . . ?
C5 N4 C3 C2 69.16(15) . . . . ?
N9 C2 C3 N4 172.28(10) . . . . ?
P1 C2 C3 N4 51.80(13) . . . . ?
N9 C2 C3 C8 -64.78(14) . . . . ?
P1 C2 C3 C8 174.75(9) . . . . ?
C4C N4 C5 C6 -108.59(15) . . . . ?
C3 N4 C5 C6 55.96(15) . . . . ?
N4 C5 C6 C7 -54.14(16) . . . . ?
C5 C6 C7 C8 54.42(16) . . . . ?
C6 C7 C8 C3 -54.27(15) . . . . ?
N4 C3 C8 C7 52.88(15) . . . . ?
C2 C3 C8 C7 -71.16(14) . . . . ?
C2 N9 C10 O10 4.0(2) . . . . ?
C2 N9 C10 C11 -174.58(11) . . . . ?
O10 C10 C11 C12 -81.01(17) . . . . ?
N9 C10 C11 C12 97.61(14) . . . . ?
C10 C11 C12 C20 27.8(2) . . . . ?
C10 C11 C12 C20D -150.8(4) . . . . ?
C10 C11 C12 S13 -152.45(10) . . . . ?
C10 C11 C12 S13D 31.61(16) . . . . ?
C14 S13 C12 C20 0.23(16) . . . . ?
C14 S13 C12 C11 -179.56(11) . . . . ?
C19 S13D C12 C20D 2.5(3) . . . . ?
C19 S13D C12 C11 -179.27(11) . . . . ?
C12 S13 C14 C15 -178.75(13) . . . . ?
C12 S13 C14 C19 0.31(11) . . . . ?
C19 C14 C15 C16 0.0(2) . . . . ?
C20D C14 C15 C16 176.3(5) . . . . ?
S13 C14 C15 C16 179.00(11) . . . . ?
C14 C15 C16 C17 -0.8(2) . . . . ?
C15 C16 C17 C18 1.3(2) . . . . ?
C16 C17 C18 C19 -0.8(2) . . . . ?
C17 C18 C19 C14 0.0(2) . . . . ?
C17 C18 C19 C20 -177.3(2) . . . . ?
C17 C18 C19 S13D 177.93(14) . . . . ?
C15 C14 C19 C18 0.4(2) . . . . ?
C20D C14 C19 C18 -177.3(3) . . . . ?
S13 C14 C19 C18 -178.65(11) . . . . ?
C15 C14 C19 C20 178.40(16) . . . . ?
S13 C14 C19 C20 -0.69(18) . . . . ?
C15 C14 C19 S13D -177.23(13) . . . . ?
C20D C14 C19 S13D 5.0(3) . . . . ?
C12 S13D C19 C18 177.27(12) . . . . ?
C12 S13D C19 C14 -4.95(16) . . . . ?
C11 C12 C20 C19 179.05(15) . . . . ?
S13 C12 C20 C19 -0.7(3) . . . . ?
C18 C19 C20 C12 178.41(17) . . . . ?
C14 C19 C20 C12 0.9(3) . . . . ?
C11 C12 C20D C14 -178.3(3) . . . . ?
S13D C12 C20D C14 -0.4(6) . . . . ?
C15 C14 C20D C12 -179.1(3) . . . . ?
C19 C14 C20D C12 -2.3(6) . . . . ?
P1 O1A C2A C3A 160.97(11) . . . . ?
P1 O1B C2B C3B -146.21(15) . . . . ?
C6C O5C C4C O4C -2.6(2) . . . . ?
C6C O5C C4C N4 178.82(12) . . . . ?
C3 N4 C4C O4C 1.9(2) . . . . ?
C5 N4 C4C O4C 166.16(14) . . . . ?
C3 N4 C4C O5C -179.52(11) . . . . ?
C5 N4 C4C O5C -15.29(19) . . . . ?
C4C O5C C6C C8C -66.76(16) . . . . ?
C4C O5C C6C C7C 175.50(13) . . . . ?
C4C O5C C6C C9C 57.87(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N9 H9 O1 0.889(13) 1.950(14) 2.8250(15) 167.5(16) 2_676 yes

_refine_diff_density_max         0.513
_refine_diff_density_min         -0.419
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_4g-1
_database_code_depnum_ccdc_archive 'CCDC 2203665'
loop_
_audit_author_name
_audit_author_address
'Arto Valkonen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2022-08-26 deposited with the CCDC.	2023-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H35 N2 O6 P S'
_chemical_formula_sum            'C24 H35 N2 O6 P S'
_chemical_formula_weight         510.57

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.2580(5)
_cell_length_b                   17.1642(5)
_cell_length_c                   14.6705(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.482(3)
_cell_angle_gamma                90
_cell_volume                     2582.95(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3867
_cell_measurement_theta_min      2.6860
_cell_measurement_theta_max      29.6620

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_F_000             1088
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.228
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.837
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0107
_diffrn_reflns_number            9815
_diffrn_reflns_av_unetI/netI     0.0823
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.313
_diffrn_reflns_theta_max         25.250
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4680
_reflns_number_gt                3302
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    SHELXL-2019/2
_computing_publication_material  SHELXL-2019/2
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1714P)²+1.0242P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4680
_refine_ls_number_parameters     310
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1065
_refine_ls_R_factor_gt           0.0782
_refine_ls_wR_factor_ref         0.2910
_refine_ls_wR_factor_gt          0.2331
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_restrained_S_all      1.107
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S12 S 0.70495(12) 0.16474(6) 0.55481(8) 0.0382(4) Uani 1 1 d . . . . .
P1 P 0.68131(11) 0.52739(6) 0.60504(7) 0.0264(4) Uani 1 1 d . . . . .
O1 O 0.5954(3) 0.57256(15) 0.5443(2) 0.0318(7) Uani 1 1 d . . . . .
O10 O 0.7326(3) 0.30298(16) 0.6663(2) 0.0367(8) Uani 1 1 d . . . . .
O1A O 0.8052(3) 0.49268(17) 0.55671(19) 0.0324(7) Uani 1 1 d . . . . .
O1B O 0.7425(3) 0.57266(15) 0.6880(2) 0.0360(8) Uani 1 1 d . . . . .
O4C O 0.3327(3) 0.60179(18) 0.7164(2) 0.0428(8) Uani 1 1 d . . . . .
O5C O 0.4252(3) 0.63218(16) 0.8528(2) 0.0371(8) Uani 1 1 d . . . . .
N4 N 0.4959(3) 0.52806(18) 0.7768(2) 0.0270(8) Uani 1 1 d . . . . .
N9 N 0.5841(3) 0.38229(17) 0.5958(2) 0.0258(8) Uani 1 1 d D . . . .
H9 H 0.535(4) 0.389(2) 0.545(2) 0.031 Uiso 1 1 d D U . . .
C2 C 0.6044(4) 0.4450(2) 0.6614(3) 0.0254(9) Uani 1 1 d . . . . .
H2 H 0.667044 0.425414 0.708664 0.031 Uiso 1 1 calc R U . . .
C3 C 0.4765(4) 0.4660(2) 0.7107(3) 0.0267(9) Uani 1 1 d . . . . .
H3 H 0.413506 0.485517 0.663539 0.032 Uiso 1 1 calc R U . . .
C5 C 0.5748(4) 0.5064(2) 0.8573(3) 0.0284(9) Uani 1 1 d . . . . .
H5A H 0.581960 0.551561 0.899077 0.034 Uiso 1 1 calc R U . . .
H5B H 0.663768 0.491761 0.838060 0.034 Uiso 1 1 calc R U . . .
C6 C 0.5118(5) 0.4385(2) 0.9064(3) 0.0359(11) Uani 1 1 d . . . . .
H6A H 0.427220 0.455360 0.931667 0.043 Uiso 1 1 calc R U . . .
H6B H 0.568520 0.422007 0.957777 0.043 Uiso 1 1 calc R U . . .
C7 C 0.4898(5) 0.3697(2) 0.8420(3) 0.0386(11) Uani 1 1 d . . . . .
H7A H 0.440840 0.328345 0.874038 0.046 Uiso 1 1 calc R U . . .
H7B H 0.575015 0.347843 0.823717 0.046 Uiso 1 1 calc R U . . .
C8 C 0.4136(5) 0.3952(2) 0.7571(3) 0.0349(10) Uani 1 1 d . . . . .
H8A H 0.323278 0.408534 0.774531 0.042 Uiso 1 1 calc R U . . .
H8B H 0.409462 0.351387 0.713341 0.042 Uiso 1 1 calc R U . . .
C10 C 0.6502(4) 0.3146(2) 0.6057(3) 0.0292(10) Uani 1 1 d . . . . .
C11 C 0.6178(4) 0.2506(2) 0.5411(3) 0.0283(9) Uani 1 1 d . . . . .
C13 C 0.6143(5) 0.1201(2) 0.4699(3) 0.0325(10) Uani 1 1 d . . . . .
C14 C 0.6288(5) 0.0435(2) 0.4375(3) 0.0398(11) Uani 1 1 d . . . . .
H14 H 0.693723 0.010141 0.462532 0.048 Uiso 1 1 calc R U . . .
C15 C 0.5477(5) 0.0180(2) 0.3694(3) 0.0418(12) Uani 1 1 d . . . . .
H15 H 0.557206 -0.033475 0.346687 0.050 Uiso 1 1 calc R U . . .
C16 C 0.4513(5) 0.0662(3) 0.3328(3) 0.0418(12) Uani 1 1 d . . . . .
H16 H 0.396643 0.047159 0.285145 0.050 Uiso 1 1 calc R U . . .
C17 C 0.4338(5) 0.1415(3) 0.3648(3) 0.0381(11) Uani 1 1 d . . . . .
H17 H 0.366010 0.173559 0.341016 0.046 Uiso 1 1 calc R U . . .
C18 C 0.5193(4) 0.1695(2) 0.4336(3) 0.0274(9) Uani 1 1 d . . . . .
C19 C 0.5241(4) 0.2453(2) 0.4751(3) 0.0273(9) Uani 1 1 d . . . . .
H19 H 0.468128 0.287095 0.458340 0.033 Uiso 1 1 calc R U . . .
C2A C 0.7995(5) 0.4648(3) 0.4629(3) 0.0374(11) Uani 1 1 d . . . . .
H2A1 H 0.707946 0.453501 0.445661 0.045 Uiso 1 1 calc R U . . .
H2A2 H 0.850159 0.415920 0.457595 0.045 Uiso 1 1 calc R U . . .
C3A C 0.8540(5) 0.5248(3) 0.4000(3) 0.0429(12) Uani 1 1 d . . . . .
H3A1 H 0.849708 0.505420 0.337161 0.064 Uiso 1 1 calc R U . . .
H3A2 H 0.803041 0.572866 0.404769 0.064 Uiso 1 1 calc R U . . .
H3A3 H 0.944990 0.535355 0.416681 0.064 Uiso 1 1 calc R U . . .
C2B C 0.7893(5) 0.6524(2) 0.6795(3) 0.0379(11) Uani 1 1 d . . . . .
H2B1 H 0.746020 0.686073 0.724905 0.046 Uiso 1 1 calc R U . . .
H2B2 H 0.768438 0.672767 0.617888 0.046 Uiso 1 1 calc R U . . .
C3B C 0.9309(6) 0.6534(3) 0.6946(5) 0.0689(19) Uani 1 1 d . . . . .
H3B1 H 0.963216 0.706916 0.689004 0.103 Uiso 1 1 calc R U . . .
H3B2 H 0.950802 0.633632 0.755808 0.103 Uiso 1 1 calc R U . . .
H3B3 H 0.973155 0.620365 0.649101 0.103 Uiso 1 1 calc R U . . .
C4C C 0.4115(4) 0.5888(2) 0.7770(3) 0.0295(9) Uani 1 1 d . . . . .
C6C C 0.3576(5) 0.7080(2) 0.8602(3) 0.0361(11) Uani 1 1 d . . . . .
C7C C 0.2114(6) 0.6957(3) 0.8626(4) 0.0548(15) Uani 1 1 d . . . . .
H7C1 H 0.167552 0.746253 0.867470 0.082 Uiso 1 1 calc R U . . .
H7C2 H 0.182865 0.669549 0.806474 0.082 Uiso 1 1 calc R U . . .
H7C3 H 0.189192 0.663394 0.915268 0.082 Uiso 1 1 calc R U . . .
C8C C 0.4066(7) 0.7391(3) 0.9504(4) 0.0656(19) Uani 1 1 d . . . . .
H8C1 H 0.367083 0.790052 0.962063 0.098 Uiso 1 1 calc R U . . .
H8C2 H 0.382935 0.702863 0.999182 0.098 Uiso 1 1 calc R U . . .
H8C3 H 0.501659 0.744497 0.948541 0.098 Uiso 1 1 calc R U . . .
C9C C 0.4019(6) 0.7603(3) 0.7845(4) 0.0492(13) Uani 1 1 d . . . . .
H9C1 H 0.357454 0.810718 0.788995 0.074 Uiso 1 1 calc R U . . .
H9C2 H 0.496332 0.768238 0.789344 0.074 Uiso 1 1 calc R U . . .
H9C3 H 0.380850 0.736229 0.725598 0.074 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S12 C13 1.728(5) . ?
S12 C11 1.734(4) . ?
P1 O1 1.469(3) . ?
P1 O1B 1.570(3) . ?
P1 O1A 1.577(3) . ?
P1 C2 1.821(4) . ?
O10 C10 1.238(5) . ?
O1A C2A 1.458(5) . ?
O1B C2B 1.457(5) . ?
O4C C4C 1.217(5) . ?
O5C C4C 1.345(5) . ?
O5C C6C 1.479(5) . ?
N4 C4C 1.356(5) . ?
N4 C3 1.453(5) . ?
N4 C5 1.474(5) . ?
N9 C10 1.353(5) . ?
N9 C2 1.457(5) . ?
N9 H9 0.911(19) . ?
C2 C3 1.546(6) . ?
C2 H2 1.0000 . ?
C3 C8 1.537(6) . ?
C3 H3 1.0000 . ?
C5 C6 1.517(6) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.528(6) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.529(6) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C10 C11 1.487(5) . ?
C11 C19 1.361(6) . ?
C13 C18 1.394(6) . ?
C13 C14 1.406(6) . ?
C14 C15 1.367(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.394(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.387(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.417(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.437(5) . ?
C19 H19 0.9500 . ?
C2A C3A 1.495(6) . ?
C2A H2A1 0.9900 . ?
C2A H2A2 0.9900 . ?
C3A H3A1 0.9800 . ?
C3A H3A2 0.9800 . ?
C3A H3A3 0.9800 . ?
C2B C3B 1.467(8) . ?
C2B H2B1 0.9900 . ?
C2B H2B2 0.9900 . ?
C3B H3B1 0.9800 . ?
C3B H3B2 0.9800 . ?
C3B H3B3 0.9800 . ?
C6C C9C 1.503(7) . ?
C6C C8C 1.509(7) . ?
C6C C7C 1.515(7) . ?
C7C H7C1 0.9800 . ?
C7C H7C2 0.9800 . ?
C7C H7C3 0.9800 . ?
C8C H8C1 0.9800 . ?
C8C H8C2 0.9800 . ?
C8C H8C3 0.9800 . ?
C9C H9C1 0.9800 . ?
C9C H9C2 0.9800 . ?
C9C H9C3 0.9800 . ?

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
C13 S12 C11 91.1(2) . . ?
O1 P1 O1B 116.27(17) . . ?
O1 P1 O1A 114.11(17) . . ?
O1B P1 O1A 102.52(17) . . ?
O1 P1 C2 115.14(19) . . ?
O1B P1 C2 101.82(17) . . ?
O1A P1 C2 105.34(17) . . ?
C2A O1A P1 121.5(3) . . ?
C2B O1B P1 121.9(3) . . ?
C4C O5C C6C 120.1(3) . . ?
C4C N4 C3 118.8(3) . . ?
C4C N4 C5 122.6(3) . . ?
C3 N4 C5 115.0(3) . . ?
C10 N9 C2 119.7(3) . . ?
C10 N9 H9 118(3) . . ?
C2 N9 H9 122(3) . . ?
N9 C2 C3 111.4(3) . . ?
N9 C2 P1 109.5(3) . . ?
C3 C2 P1 113.8(3) . . ?
N9 C2 H2 107.3 . . ?
C3 C2 H2 107.3 . . ?
P1 C2 H2 107.3 . . ?
N4 C3 C8 109.8(3) . . ?
N4 C3 C2 111.8(3) . . ?
C8 C3 C2 112.6(3) . . ?
N4 C3 H3 107.5 . . ?
C8 C3 H3 107.5 . . ?
C2 C3 H3 107.5 . . ?
N4 C5 C6 109.9(3) . . ?
N4 C5 H5A 109.7 . . ?
C6 C5 H5A 109.7 . . ?
N4 C5 H5B 109.7 . . ?
C6 C5 H5B 109.7 . . ?
H5A C5 H5B 108.2 . . ?
C5 C6 C7 111.3(3) . . ?
C5 C6 H6A 109.4 . . ?
C7 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
C7 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C6 C7 C8 110.7(4) . . ?
C6 C7 H7A 109.5 . . ?
C8 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C7 C8 C3 112.0(4) . . ?
C7 C8 H8A 109.2 . . ?
C3 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
C3 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
O10 C10 N9 123.6(4) . . ?
O10 C10 C11 119.2(4) . . ?
N9 C10 C11 117.2(4) . . ?
C19 C11 C10 131.0(4) . . ?
C19 C11 S12 112.7(3) . . ?
C10 C11 S12 116.2(3) . . ?
C18 C13 C14 121.1(4) . . ?
C18 C13 S12 112.1(3) . . ?
C14 C13 S12 126.9(4) . . ?
C15 C14 C13 118.7(5) . . ?
C15 C14 H14 120.6 . . ?
C13 C14 H14 120.6 . . ?
C14 C15 C16 121.2(4) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C17 C16 C15 121.1(5) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C18 118.4(5) . . ?
C16 C17 H17 120.8 . . ?
C18 C17 H17 120.8 . . ?
C13 C18 C17 119.5(4) . . ?
C13 C18 C19 111.6(4) . . ?
C17 C18 C19 128.9(4) . . ?
C11 C19 C18 112.5(4) . . ?
C11 C19 H19 123.8 . . ?
C18 C19 H19 123.8 . . ?
O1A C2A C3A 110.2(4) . . ?
O1A C2A H2A1 109.6 . . ?
C3A C2A H2A1 109.6 . . ?
O1A C2A H2A2 109.6 . . ?
C3A C2A H2A2 109.6 . . ?
H2A1 C2A H2A2 108.1 . . ?
C2A C3A H3A1 109.5 . . ?
C2A C3A H3A2 109.5 . . ?
H3A1 C3A H3A2 109.5 . . ?
C2A C3A H3A3 109.5 . . ?
H3A1 C3A H3A3 109.5 . . ?
H3A2 C3A H3A3 109.5 . . ?
O1B C2B C3B 108.9(4) . . ?
O1B C2B H2B1 109.9 . . ?
C3B C2B H2B1 109.9 . . ?
O1B C2B H2B2 109.9 . . ?
C3B C2B H2B2 109.9 . . ?
H2B1 C2B H2B2 108.3 . . ?
C2B C3B H3B1 109.5 . . ?
C2B C3B H3B2 109.5 . . ?
H3B1 C3B H3B2 109.5 . . ?
C2B C3B H3B3 109.5 . . ?
H3B1 C3B H3B3 109.5 . . ?
H3B2 C3B H3B3 109.5 . . ?
O4C C4C O5C 124.5(4) . . ?
O4C C4C N4 124.0(4) . . ?
O5C C4C N4 111.4(4) . . ?
O5C C6C C9C 109.1(4) . . ?
O5C C6C C8C 102.9(4) . . ?
C9C C6C C8C 109.7(4) . . ?
O5C C6C C7C 110.1(4) . . ?
C9C C6C C7C 113.9(4) . . ?
C8C C6C C7C 110.6(5) . . ?
C6C C7C H7C1 109.5 . . ?
C6C C7C H7C2 109.5 . . ?
H7C1 C7C H7C2 109.5 . . ?
C6C C7C H7C3 109.5 . . ?
H7C1 C7C H7C3 109.5 . . ?
H7C2 C7C H7C3 109.5 . . ?
C6C C8C H8C1 109.5 . . ?
C6C C8C H8C2 109.5 . . ?
H8C1 C8C H8C2 109.5 . . ?
C6C C8C H8C3 109.5 . . ?
H8C1 C8C H8C3 109.5 . . ?
H8C2 C8C H8C3 109.5 . . ?
C6C C9C H9C1 109.5 . . ?
C6C C9C H9C2 109.5 . . ?
H9C1 C9C H9C2 109.5 . . ?
C6C C9C H9C3 109.5 . . ?
H9C1 C9C H9C3 109.5 . . ?
H9C2 C9C H9C3 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
O1 P1 O1A C2A -35.8(3) . . . . ?
O1B P1 O1A C2A -162.4(3) . . . . ?
C2 P1 O1A C2A 91.5(3) . . . . ?
O1 P1 O1B C2B -39.7(4) . . . . ?
O1A P1 O1B C2B 85.5(4) . . . . ?
C2 P1 O1B C2B -165.7(3) . . . . ?
C10 N9 C2 C3 -119.4(4) . . . . ?
C10 N9 C2 P1 113.9(3) . . . . ?
O1 P1 C2 N9 74.1(3) . . . . ?
O1B P1 C2 N9 -159.2(3) . . . . ?
O1A P1 C2 N9 -52.5(3) . . . . ?
O1 P1 C2 C3 -51.3(3) . . . . ?
O1B P1 C2 C3 75.4(3) . . . . ?
O1A P1 C2 C3 -177.9(3) . . . . ?
C4C N4 C3 C8 -102.1(4) . . . . ?
C5 N4 C3 C8 56.7(5) . . . . ?
C4C N4 C3 C2 132.2(4) . . . . ?
C5 N4 C3 C2 -68.9(4) . . . . ?
N9 C2 C3 N4 179.5(3) . . . . ?
P1 C2 C3 N4 -56.1(4) . . . . ?
N9 C2 C3 C8 55.4(4) . . . . ?
P1 C2 C3 C8 179.7(3) . . . . ?
C4C N4 C5 C6 99.6(4) . . . . ?
C3 N4 C5 C6 -58.4(5) . . . . ?
N4 C5 C6 C7 55.1(5) . . . . ?
C5 C6 C7 C8 -53.6(5) . . . . ?
C6 C7 C8 C3 52.4(5) . . . . ?
N4 C3 C8 C7 -52.9(5) . . . . ?
C2 C3 C8 C7 72.4(4) . . . . ?
C2 N9 C10 O10 -2.9(6) . . . . ?
C2 N9 C10 C11 175.3(4) . . . . ?
O10 C10 C11 C19 173.0(4) . . . . ?
N9 C10 C11 C19 -5.3(7) . . . . ?
O10 C10 C11 S12 -2.2(5) . . . . ?
N9 C10 C11 S12 179.5(3) . . . . ?
C13 S12 C11 C19 0.1(3) . . . . ?
C13 S12 C11 C10 176.2(3) . . . . ?
C11 S12 C13 C18 -0.9(3) . . . . ?
C11 S12 C13 C14 179.1(4) . . . . ?
C18 C13 C14 C15 0.0(7) . . . . ?
S12 C13 C14 C15 -180.0(4) . . . . ?
C13 C14 C15 C16 -0.6(7) . . . . ?
C14 C15 C16 C17 -0.5(7) . . . . ?
C15 C16 C17 C18 2.2(7) . . . . ?
C14 C13 C18 C17 1.7(6) . . . . ?
S12 C13 C18 C17 -178.4(3) . . . . ?
C14 C13 C18 C19 -178.6(4) . . . . ?
S12 C13 C18 C19 1.4(5) . . . . ?
C16 C17 C18 C13 -2.7(6) . . . . ?
C16 C17 C18 C19 177.6(4) . . . . ?
C10 C11 C19 C18 -174.6(4) . . . . ?
S12 C11 C19 C18 0.7(5) . . . . ?
C13 C18 C19 C11 -1.4(5) . . . . ?
C17 C18 C19 C11 178.4(4) . . . . ?
P1 O1A C2A C3A 100.4(4) . . . . ?
P1 O1B C2B C3B -115.1(5) . . . . ?
C6C O5C C4C O4C -10.4(7) . . . . ?
C6C O5C C4C N4 170.3(4) . . . . ?
C3 N4 C4C O4C -12.5(7) . . . . ?
C5 N4 C4C O4C -169.7(4) . . . . ?
C3 N4 C4C O5C 166.8(4) . . . . ?
C5 N4 C4C O5C 9.7(5) . . . . ?
C4C O5C C6C C9C -59.4(6) . . . . ?
C4C O5C C6C C8C -175.8(4) . . . . ?
C4C O5C C6C C7C 66.3(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N9 H9 O1 0.911(19) 1.97(2) 2.856(4) 163(4) 3_666 yes

_refine_diff_density_max         0.938
_refine_diff_density_min         -0.951
_refine_diff_density_rms         0.110

####################################################################### 
# 
# 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_4e-2b
_database_code_depnum_ccdc_archive 'CCDC 2203670'
loop_
_audit_author_name
_audit_author_address
'Arto Valkonen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2022-08-26 deposited with the CCDC.	2023-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/2
_shelx_SHELXL_version_number     2019/2
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H39 N2 O6 P S'
_chemical_formula_sum            'C24 H39 N2 O6 P S'
_chemical_formula_weight         514.60

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   11.33250(10)
_cell_length_b                   14.4994(2)
_cell_length_c                   16.6241(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.0090(10)
_cell_angle_gamma                90
_cell_volume                     2727.81(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    10580
_cell_measurement_theta_min      2.6270
_cell_measurement_theta_max      29.5070

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_F_000             1104
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.217
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.847
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0107
_diffrn_reflns_number            27198
_diffrn_reflns_av_unetI/netI     0.0325
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.124
_diffrn_reflns_theta_max         29.960
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.909
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.909
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.909
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             7199
_reflns_number_gt                5785
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    SHELXL-2019/2
_computing_publication_material  SHELXL-2019/2
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0409P)²+1.6464P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7199
_refine_ls_number_parameters     310
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0574
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.1088
_refine_ls_wR_factor_gt          0.1002
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S13 S 0.33258(4) 0.85569(3) 0.59684(3) 0.02992(11) Uani 1 1 d . . . . .
P1 P 0.69845(3) 0.52520(3) 0.44177(2) 0.01767(9) Uani 1 1 d . . . . .
O1 O 0.64502(10) 0.45293(7) 0.49034(7) 0.0234(2) Uani 1 1 d . . . . .
O10 O 0.60664(10) 0.78587(8) 0.38968(7) 0.0258(3) Uani 1 1 d . . . . .
O1A O 0.77875(10) 0.59590(8) 0.49115(7) 0.0236(2) Uani 1 1 d . . . . .
O1B O 0.78565(10) 0.49131(8) 0.37790(7) 0.0270(3) Uani 1 1 d . . . . .
O4C O 0.46002(11) 0.35471(8) 0.29611(7) 0.0271(3) Uani 1 1 d . . . . .
O5C O 0.53918(11) 0.37714(7) 0.17466(7) 0.0246(2) Uani 1 1 d . . . . .
N4 N 0.55464(11) 0.48870(9) 0.26770(7) 0.0202(3) Uani 1 1 d . . . . .
N9 N 0.53084(11) 0.65392(8) 0.44002(7) 0.0172(2) Uani 1 1 d D . . . .
H9 H 0.4733(14) 0.6276(12) 0.4658(10) 0.021 Uiso 1 1 d D U . . .
C2 C 0.59136(13) 0.59511(10) 0.38454(9) 0.0173(3) Uani 1 1 d . . . . .
H2 H 0.634813 0.635427 0.347280 0.021 Uiso 1 1 calc R U . . .
C3 C 0.49923(13) 0.53790(10) 0.33364(9) 0.0196(3) Uani 1 1 d . . . . .
H3 H 0.465201 0.490776 0.369735 0.024 Uiso 1 1 calc R U . . .
C5 C 0.60035(15) 0.54919(11) 0.20549(9) 0.0250(3) Uani 1 1 d . . . . .
H5A H 0.634958 0.511131 0.163260 0.030 Uiso 1 1 calc R U . . .
H5B H 0.663579 0.588975 0.229880 0.030 Uiso 1 1 calc R U . . .
C6 C 0.50218(18) 0.60923(13) 0.16762(10) 0.0338(4) Uani 1 1 d . . . . .
H6A H 0.445287 0.570016 0.135982 0.041 Uiso 1 1 calc R U . . .
H6B H 0.536327 0.654025 0.130377 0.041 Uiso 1 1 calc R U . . .
C7 C 0.43728(18) 0.66137(13) 0.23228(11) 0.0350(4) Uani 1 1 d . . . . .
H7A H 0.490381 0.708806 0.257160 0.042 Uiso 1 1 calc R U . . .
H7B H 0.367541 0.693143 0.206877 0.042 Uiso 1 1 calc R U . . .
C8 C 0.39741(15) 0.59615(12) 0.29725(10) 0.0279(4) Uani 1 1 d . . . . .
H8A H 0.335228 0.554775 0.273752 0.034 Uiso 1 1 calc R U . . .
H8B H 0.362624 0.632539 0.340477 0.034 Uiso 1 1 calc R U . . .
C10 C 0.53787(13) 0.74715(10) 0.43338(9) 0.0184(3) Uani 1 1 d . . . . .
C11 C 0.45490(13) 0.79993(10) 0.48232(9) 0.0192(3) Uani 1 1 d . . . . .
C12 C 0.42393(15) 0.77524(11) 0.55725(10) 0.0242(3) Uani 1 1 d . . . . .
H12 H 0.449613 0.720452 0.584188 0.029 Uiso 1 1 calc R U . . .
C14 C 0.33381(14) 0.92333(11) 0.51154(10) 0.0238(3) Uani 1 1 d . . . . .
C15 C 0.26512(16) 1.01173(12) 0.50252(11) 0.0300(4) Uani 1 1 d . . . . .
H15A H 0.276581 1.049061 0.552179 0.036 Uiso 1 1 calc R U . . .
H15B H 0.179811 0.997925 0.494093 0.036 Uiso 1 1 calc R U . . .
C16 C 0.30761(16) 1.06590(11) 0.43058(11) 0.0306(4) Uani 1 1 d . . . . .
H16A H 0.249800 1.115100 0.416005 0.037 Uiso 1 1 calc R U . . .
H16B H 0.384112 1.095691 0.445925 0.037 Uiso 1 1 calc R U . . .
C17 C 0.32249(16) 1.00394(12) 0.35780(11) 0.0295(4) Uani 1 1 d . . . . .
H17A H 0.343774 1.042097 0.311349 0.035 Uiso 1 1 calc R U . . .
H17B H 0.246592 0.972799 0.343283 0.035 Uiso 1 1 calc R U . . .
C18 C 0.41828(15) 0.93141(11) 0.37508(10) 0.0254(3) Uani 1 1 d . . . . .
H18A H 0.414060 0.884135 0.332052 0.031 Uiso 1 1 calc R U . . .
H18B H 0.497035 0.960971 0.375165 0.031 Uiso 1 1 calc R U . . .
C19 C 0.40295(13) 0.88590(10) 0.45547(9) 0.0199(3) Uani 1 1 d . . . . .
C2A C 0.74686(18) 0.62987(13) 0.56969(10) 0.0346(4) Uani 1 1 d . . . . .
H2A H 0.665971 0.609141 0.580478 0.041 Uiso 1 1 calc R U . . .
H2B H 0.747514 0.698151 0.569650 0.041 Uiso 1 1 calc R U . . .
C3A C 0.8307(2) 0.5954(2) 0.63349(14) 0.0722(9) Uani 1 1 d . . . . .
H3A H 0.808090 0.618832 0.685811 0.108 Uiso 1 1 calc R U . . .
H3B H 0.829117 0.527873 0.633948 0.108 Uiso 1 1 calc R U . . .
H3C H 0.910528 0.616738 0.623137 0.108 Uiso 1 1 calc R U . . .
C2B C 0.8131(2) 0.39627(15) 0.36598(18) 0.0634(8) Uani 1 1 d . . . . .
H2C H 0.742994 0.357860 0.375596 0.076 Uiso 1 1 calc R U . . .
H2D H 0.877902 0.377258 0.404698 0.076 Uiso 1 1 calc R U . . .
C3B C 0.8493(2) 0.3822(2) 0.28269(18) 0.0788(10) Uani 1 1 d . . . . .
H3D H 0.868022 0.316954 0.274685 0.118 Uiso 1 1 calc R U . . .
H3E H 0.784558 0.400450 0.244582 0.118 Uiso 1 1 calc R U . . .
H3F H 0.919156 0.419804 0.273616 0.118 Uiso 1 1 calc R U . . .
C4C C 0.51269(13) 0.40233(10) 0.24941(9) 0.0198(3) Uani 1 1 d . . . . .
C6C C 0.51164(15) 0.28327(11) 0.14337(10) 0.0248(3) Uani 1 1 d . . . . .
C7C C 0.37953(17) 0.26703(14) 0.13928(13) 0.0404(5) Uani 1 1 d . . . . .
H7C H 0.362634 0.204883 0.118550 0.061 Uiso 1 1 calc R U . . .
H7D H 0.349671 0.273026 0.193298 0.061 Uiso 1 1 calc R U . . .
H7E H 0.340737 0.312662 0.103340 0.061 Uiso 1 1 calc R U . . .
C8C C 0.5589(2) 0.28809(13) 0.05960(11) 0.0401(5) Uani 1 1 d . . . . .
H8C H 0.545667 0.228873 0.032173 0.060 Uiso 1 1 calc R U . . .
H8D H 0.517774 0.337039 0.028666 0.060 Uiso 1 1 calc R U . . .
H8E H 0.643772 0.301459 0.063949 0.060 Uiso 1 1 calc R U . . .
C9C C 0.5795(2) 0.21236(13) 0.19374(12) 0.0424(5) Uani 1 1 d . . . . .
H9C H 0.561081 0.150519 0.172871 0.064 Uiso 1 1 calc R U . . .
H9D H 0.664474 0.223904 0.191279 0.064 Uiso 1 1 calc R U . . .
H9E H 0.557089 0.216653 0.249752 0.064 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S13 C12 1.7138(16) . ?
S13 C14 1.7248(17) . ?
P1 O1 1.4725(11) . ?
P1 O1B 1.5671(11) . ?
P1 O1A 1.5730(11) . ?
P1 C2 1.8122(15) . ?
O10 C10 1.2287(18) . ?
O1A C2A 1.459(2) . ?
O1B C2B 1.429(2) . ?
O4C C4C 1.2182(19) . ?
O5C C4C 1.3442(18) . ?
O5C C6C 1.4845(18) . ?
N4 C4C 1.368(2) . ?
N4 C5 1.4709(19) . ?
N4 C3 1.4754(18) . ?
N9 C10 1.3591(19) . ?
N9 C2 1.4540(18) . ?
N9 H9 0.886(14) . ?
C2 C3 1.550(2) . ?
C2 H2 1.0000 . ?
C3 C8 1.529(2) . ?
C3 H3 1.0000 . ?
C5 C6 1.523(3) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.533(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.522(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C10 C11 1.487(2) . ?
C11 C12 1.360(2) . ?
C11 C19 1.439(2) . ?
C12 H12 0.9500 . ?
C14 C19 1.362(2) . ?
C14 C15 1.503(2) . ?
C15 C16 1.529(3) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.523(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 C18 1.528(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C19 1.509(2) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C2A C3A 1.473(3) . ?
C2A H2A 0.9900 . ?
C2A H2B 0.9900 . ?
C3A H3A 0.9800 . ?
C3A H3B 0.9800 . ?
C3A H3C 0.9800 . ?
C2B C3B 1.479(3) . ?
C2B H2C 0.9900 . ?
C2B H2D 0.9900 . ?
C3B H3D 0.9800 . ?
C3B H3E 0.9800 . ?
C3B H3F 0.9800 . ?
C6C C9C 1.511(2) . ?
C6C C7C 1.514(3) . ?
C6C C8C 1.520(2) . ?
C7C H7C 0.9800 . ?
C7C H7D 0.9800 . ?
C7C H7E 0.9800 . ?
C8C H8C 0.9800 . ?
C8C H8D 0.9800 . ?
C8C H8E 0.9800 . ?
C9C H9C 0.9800 . ?
C9C H9D 0.9800 . ?
C9C H9E 0.9800 . ?

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
C12 S13 C14 92.30(8) . . ?
O1 P1 O1B 116.13(7) . . ?
O1 P1 O1A 114.89(7) . . ?
O1B P1 O1A 100.94(6) . . ?
O1 P1 C2 113.74(7) . . ?
O1B P1 C2 104.39(7) . . ?
O1A P1 C2 105.22(7) . . ?
C2A O1A P1 121.56(10) . . ?
C2B O1B P1 123.10(12) . . ?
C4C O5C C6C 121.33(12) . . ?
C4C N4 C5 121.38(12) . . ?
C4C N4 C3 116.82(12) . . ?
C5 N4 C3 114.42(12) . . ?
C10 N9 C2 120.01(12) . . ?
C10 N9 H9 121.1(11) . . ?
C2 N9 H9 116.0(12) . . ?
N9 C2 C3 109.49(12) . . ?
N9 C2 P1 108.68(10) . . ?
C3 C2 P1 113.62(10) . . ?
N9 C2 H2 108.3 . . ?
C3 C2 H2 108.3 . . ?
P1 C2 H2 108.3 . . ?
N4 C3 C8 108.36(12) . . ?
N4 C3 C2 111.33(12) . . ?
C8 C3 C2 113.15(13) . . ?
N4 C3 H3 107.9 . . ?
C8 C3 H3 107.9 . . ?
C2 C3 H3 107.9 . . ?
N4 C5 C6 110.79(14) . . ?
N4 C5 H5A 109.5 . . ?
C6 C5 H5A 109.5 . . ?
N4 C5 H5B 109.5 . . ?
C6 C5 H5B 109.5 . . ?
H5A C5 H5B 108.1 . . ?
C5 C6 C7 111.04(14) . . ?
C5 C6 H6A 109.4 . . ?
C7 C6 H6A 109.4 . . ?
C5 C6 H6B 109.4 . . ?
C7 C6 H6B 109.4 . . ?
H6A C6 H6B 108.0 . . ?
C8 C7 C6 111.24(15) . . ?
C8 C7 H7A 109.4 . . ?
C6 C7 H7A 109.4 . . ?
C8 C7 H7B 109.4 . . ?
C6 C7 H7B 109.4 . . ?
H7A C7 H7B 108.0 . . ?
C7 C8 C3 112.22(14) . . ?
C7 C8 H8A 109.2 . . ?
C3 C8 H8A 109.2 . . ?
C7 C8 H8B 109.2 . . ?
C3 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
O10 C10 N9 122.97(14) . . ?
O10 C10 C11 121.82(13) . . ?
N9 C10 C11 115.21(13) . . ?
C12 C11 C19 113.02(14) . . ?
C12 C11 C10 124.52(14) . . ?
C19 C11 C10 122.40(13) . . ?
C11 C12 S13 111.27(12) . . ?
C11 C12 H12 124.4 . . ?
S13 C12 H12 124.4 . . ?
C19 C14 C15 125.81(15) . . ?
C19 C14 S13 111.47(12) . . ?
C15 C14 S13 122.72(13) . . ?
C14 C15 C16 109.47(14) . . ?
C14 C15 H15A 109.8 . . ?
C16 C15 H15A 109.8 . . ?
C14 C15 H15B 109.8 . . ?
C16 C15 H15B 109.8 . . ?
H15A C15 H15B 108.2 . . ?
C17 C16 C15 111.76(14) . . ?
C17 C16 H16A 109.3 . . ?
C15 C16 H16A 109.3 . . ?
C17 C16 H16B 109.3 . . ?
C15 C16 H16B 109.3 . . ?
H16A C16 H16B 107.9 . . ?
C16 C17 C18 111.33(14) . . ?
C16 C17 H17A 109.4 . . ?
C18 C17 H17A 109.4 . . ?
C16 C17 H17B 109.4 . . ?
C18 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C19 C18 C17 110.72(14) . . ?
C19 C18 H18A 109.5 . . ?
C17 C18 H18A 109.5 . . ?
C19 C18 H18B 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 108.1 . . ?
C14 C19 C11 111.93(14) . . ?
C14 C19 C18 121.96(14) . . ?
C11 C19 C18 126.10(14) . . ?
O1A C2A C3A 110.45(19) . . ?
O1A C2A H2A 109.6 . . ?
C3A C2A H2A 109.6 . . ?
O1A C2A H2B 109.6 . . ?
C3A C2A H2B 109.6 . . ?
H2A C2A H2B 108.1 . . ?
C2A C3A H3A 109.5 . . ?
C2A C3A H3B 109.5 . . ?
H3A C3A H3B 109.5 . . ?
C2A C3A H3C 109.5 . . ?
H3A C3A H3C 109.5 . . ?
H3B C3A H3C 109.5 . . ?
O1B C2B C3B 109.6(2) . . ?
O1B C2B H2C 109.7 . . ?
C3B C2B H2C 109.7 . . ?
O1B C2B H2D 109.7 . . ?
C3B C2B H2D 109.7 . . ?
H2C C2B H2D 108.2 . . ?
C2B C3B H3D 109.5 . . ?
C2B C3B H3E 109.5 . . ?
H3D C3B H3E 109.5 . . ?
C2B C3B H3F 109.5 . . ?
H3D C3B H3F 109.5 . . ?
H3E C3B H3F 109.5 . . ?
O4C C4C O5C 125.16(14) . . ?
O4C C4C N4 123.59(14) . . ?
O5C C4C N4 111.24(13) . . ?
O5C C6C C9C 109.76(14) . . ?
O5C C6C C7C 110.34(13) . . ?
C9C C6C C7C 113.13(17) . . ?
O5C C6C C8C 101.61(13) . . ?
C9C C6C C8C 110.21(16) . . ?
C7C C6C C8C 111.19(16) . . ?
C6C C7C H7C 109.5 . . ?
C6C C7C H7D 109.5 . . ?
H7C C7C H7D 109.5 . . ?
C6C C7C H7E 109.5 . . ?
H7C C7C H7E 109.5 . . ?
H7D C7C H7E 109.5 . . ?
C6C C8C H8C 109.5 . . ?
C6C C8C H8D 109.5 . . ?
H8C C8C H8D 109.5 . . ?
C6C C8C H8E 109.5 . . ?
H8C C8C H8E 109.5 . . ?
H8D C8C H8E 109.5 . . ?
C6C C9C H9C 109.5 . . ?
C6C C9C H9D 109.5 . . ?
H9C C9C H9D 109.5 . . ?
C6C C9C H9E 109.5 . . ?
H9C C9C H9E 109.5 . . ?
H9D C9C H9E 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
O1 P1 O1A C2A -39.17(15) . . . . ?
O1B P1 O1A C2A -164.92(13) . . . . ?
C2 P1 O1A C2A 86.73(13) . . . . ?
O1 P1 O1B C2B 0.2(2) . . . . ?
O1A P1 O1B C2B 125.11(19) . . . . ?
C2 P1 O1B C2B -125.88(19) . . . . ?
C10 N9 C2 C3 -116.32(15) . . . . ?
C10 N9 C2 P1 119.05(13) . . . . ?
O1 P1 C2 N9 71.12(11) . . . . ?
O1B P1 C2 N9 -161.32(9) . . . . ?
O1A P1 C2 N9 -55.49(11) . . . . ?
O1 P1 C2 C3 -51.03(12) . . . . ?
O1B P1 C2 C3 76.53(11) . . . . ?
O1A P1 C2 C3 -177.63(10) . . . . ?
C4C N4 C3 C8 -91.99(16) . . . . ?
C5 N4 C3 C8 58.51(16) . . . . ?
C4C N4 C3 C2 142.96(13) . . . . ?
C5 N4 C3 C2 -66.54(16) . . . . ?
N9 C2 C3 N4 170.73(12) . . . . ?
P1 C2 C3 N4 -67.58(14) . . . . ?
N9 C2 C3 C8 48.40(16) . . . . ?
P1 C2 C3 C8 170.10(11) . . . . ?
C4C N4 C5 C6 90.63(17) . . . . ?
C3 N4 C5 C6 -58.38(17) . . . . ?
N4 C5 C6 C7 52.92(19) . . . . ?
C5 C6 C7 C8 -51.5(2) . . . . ?
C6 C7 C8 C3 53.62(19) . . . . ?
N4 C3 C8 C7 -55.35(17) . . . . ?
C2 C3 C8 C7 68.62(17) . . . . ?
C2 N9 C10 O10 -10.6(2) . . . . ?
C2 N9 C10 C11 168.76(13) . . . . ?
O10 C10 C11 C12 -143.85(17) . . . . ?
N9 C10 C11 C12 36.8(2) . . . . ?
O10 C10 C11 C19 33.3(2) . . . . ?
N9 C10 C11 C19 -146.04(14) . . . . ?
C19 C11 C12 S13 -0.46(18) . . . . ?
C10 C11 C12 S13 176.92(12) . . . . ?
C14 S13 C12 C11 0.68(14) . . . . ?
C12 S13 C14 C19 -0.75(13) . . . . ?
C12 S13 C14 C15 178.85(15) . . . . ?
C19 C14 C15 C16 -14.0(2) . . . . ?
S13 C14 C15 C16 166.43(12) . . . . ?
C14 C15 C16 C17 44.41(19) . . . . ?
C15 C16 C17 C18 -63.53(19) . . . . ?
C16 C17 C18 C19 46.74(19) . . . . ?
C15 C14 C19 C11 -178.97(15) . . . . ?
S13 C14 C19 C11 0.62(17) . . . . ?
C15 C14 C19 C18 0.0(3) . . . . ?
S13 C14 C19 C18 179.59(12) . . . . ?
C12 C11 C19 C14 -0.1(2) . . . . ?
C10 C11 C19 C14 -177.55(14) . . . . ?
C12 C11 C19 C18 -179.03(15) . . . . ?
C10 C11 C19 C18 3.5(2) . . . . ?
C17 C18 C19 C14 -16.3(2) . . . . ?
C17 C18 C19 C11 162.53(15) . . . . ?
P1 O1A C2A C3A 112.49(18) . . . . ?
P1 O1B C2B C3B 154.12(16) . . . . ?
C6C O5C C4C O4C -3.9(2) . . . . ?
C6C O5C C4C N4 174.95(13) . . . . ?
C5 N4 C4C O4C -169.97(15) . . . . ?
C3 N4 C4C O4C -21.7(2) . . . . ?
C5 N4 C4C O5C 11.2(2) . . . . ?
C3 N4 C4C O5C 159.50(13) . . . . ?
C4C O5C C6C C9C -62.5(2) . . . . ?
C4C O5C C6C C7C 62.85(19) . . . . ?
C4C O5C C6C C8C -179.13(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N9 H9 O1 0.886(14) 1.947(14) 2.8203(16) 168.1(17) 3_666 yes

_refine_diff_density_max         0.385
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_4j-1
_database_code_depnum_ccdc_archive 'CCDC 2203667'
loop_
_audit_author_name
_audit_author_address
'Arto Valkonen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2022-08-26 deposited with the CCDC.	2023-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H35 N2 O6 P S'
_chemical_formula_weight         474.54

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'
S S 0.1246 0.1234 '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'

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.8287(4)
_cell_length_b                   10.6334(6)
_cell_length_c                   14.2157(7)
_cell_angle_alpha                109.022(5)
_cell_angle_beta                 90.103(4)
_cell_angle_gamma                99.548(4)
_cell_volume                     1241.97(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3282
_cell_measurement_theta_min      2.7070
_cell_measurement_theta_max      29.5290

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_F_000             508
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.232
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.979
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_T_max  0.985
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0107
_diffrn_reflns_number            10578
_diffrn_reflns_av_unetI/netI     0.0463
_diffrn_reflns_av_R_equivalents  0.0208
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.058
_diffrn_reflns_theta_max         29.787
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.875
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.875
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.875
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6223
_reflns_number_gt                4935
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    SHELXL-2018/3
_computing_publication_material  SHELXL-2018/3
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0348P)²+0.5856P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6223
_refine_ls_number_parameters     283
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0431
_refine_ls_wR_factor_ref         0.1023
_refine_ls_wR_factor_gt          0.0934
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S14 S 0.14100(6) 0.01995(5) 0.24541(3) 0.02859(12) Uani 1 1 d . . . . .
P1 P 0.52756(5) 0.38977(4) 0.63131(3) 0.01727(10) Uani 1 1 d . . . . .
O1 O 0.62789(14) 0.46535(13) 0.57780(9) 0.0245(3) Uani 1 1 d . . . . .
O10 O 0.05971(14) 0.31109(12) 0.62197(9) 0.0243(3) Uani 1 1 d . . . . .
O1A O 0.47141(14) 0.23633(12) 0.56848(9) 0.0231(3) Uani 1 1 d . . . . .
O1B O 0.59898(14) 0.38220(12) 0.72992(8) 0.0213(3) Uani 1 1 d . . . . .
O4C O 0.65304(17) 0.76488(15) 0.84550(10) 0.0418(4) Uani 1 1 d . . . . .
O5C O 0.56393(14) 0.73715(12) 0.98824(9) 0.0251(3) Uani 1 1 d . . . . .
N4 N 0.43392(16) 0.61725(14) 0.84229(10) 0.0186(3) Uani 1 1 d . . . . .
N9 N 0.26301(16) 0.43936(14) 0.58050(10) 0.0165(3) Uani 1 1 d D . . . .
H9 H 0.300(2) 0.4707(18) 0.5338(12) 0.020 Uiso 1 1 d D U . . .
C2 C 0.35491(19) 0.45911(16) 0.67118(11) 0.0160(3) Uani 1 1 d . . . . .
H2 H 0.296086 0.403815 0.708500 0.019 Uiso 1 1 calc R U . . .
C3 C 0.3864(2) 0.60913(16) 0.74084(12) 0.0195(3) Uani 1 1 d . . . . .
H3 H 0.473167 0.658907 0.714688 0.023 Uiso 1 1 calc R U . . .
C5 C 0.3133(2) 0.56623(17) 0.89812(12) 0.0198(3) Uani 1 1 d . . . . .
H5A H 0.356343 0.577602 0.965346 0.024 Uiso 1 1 calc R U . . .
H5B H 0.276881 0.468561 0.863423 0.024 Uiso 1 1 calc R U . . .
C6 C 0.1788(2) 0.64104(19) 0.90782(13) 0.0266(4) Uani 1 1 d . . . . .
H6A H 0.212257 0.736901 0.949100 0.032 Uiso 1 1 calc R U . . .
H6B H 0.095570 0.600640 0.941233 0.032 Uiso 1 1 calc R U . . .
C7 C 0.1189(2) 0.6325(2) 0.80469(14) 0.0304(4) Uani 1 1 d . . . . .
H7A H 0.072429 0.537792 0.766905 0.037 Uiso 1 1 calc R U . . .
H7B H 0.037774 0.688527 0.811865 0.037 Uiso 1 1 calc R U . . .
C8 C 0.2481(2) 0.68127(18) 0.74711(13) 0.0278(4) Uani 1 1 d . . . . .
H8A H 0.283095 0.779598 0.779792 0.033 Uiso 1 1 calc R U . . .
H8B H 0.207404 0.666703 0.678728 0.033 Uiso 1 1 calc R U . . .
C10 C 0.12066(19) 0.36262(16) 0.56264(12) 0.0176(3) Uani 1 1 d . . . . .
C11 C 0.0404(2) 0.34096(17) 0.46258(12) 0.0204(3) Uani 1 1 d . . . . .
H11A H -0.069673 0.347100 0.471229 0.024 Uiso 1 1 calc R U . . .
H11B H 0.087342 0.412242 0.435552 0.024 Uiso 1 1 calc R U . . .
C12 C 0.05490(19) 0.20372(16) 0.39049(12) 0.0185(3) Uani 1 1 d . . . . .
C13 C 0.1366(2) 0.18698(17) 0.30777(13) 0.0230(4) Uani 1 1 d . . . . .
H13 H 0.185391 0.259211 0.286925 0.028 Uiso 1 1 calc R U . . .
C15 C 0.0312(2) -0.02956(18) 0.33087(14) 0.0270(4) Uani 1 1 d . . . . .
H15 H 0.000582 -0.120854 0.327778 0.032 Uiso 1 1 calc R U . . .
C16 C -0.0067(2) 0.07850(17) 0.40372(13) 0.0232(4) Uani 1 1 d . . . . .
H16 H -0.067384 0.071096 0.457401 0.028 Uiso 1 1 calc R U . . .
C2A C 0.4474(2) 0.18952(19) 0.46046(13) 0.0283(4) Uani 1 1 d . . . . .
H2A1 H 0.446245 0.267793 0.437457 0.034 Uiso 1 1 calc R U . . .
H2A2 H 0.346519 0.128785 0.440302 0.034 Uiso 1 1 calc R U . . .
C3A C 0.5723(3) 0.1157(2) 0.41269(17) 0.0412(5) Uani 1 1 d . . . . .
H3A1 H 0.554411 0.084877 0.340047 0.062 Uiso 1 1 calc R U . . .
H3A2 H 0.671977 0.176266 0.431937 0.062 Uiso 1 1 calc R U . . .
H3A3 H 0.572406 0.037474 0.434777 0.062 Uiso 1 1 calc R U . . .
C2B C 0.7384(2) 0.3249(2) 0.72622(14) 0.0350(5) Uani 1 1 d . . . . .
H2B1 H 0.816850 0.366955 0.690666 0.042 Uiso 1 1 calc R U . . .
H2B2 H 0.715825 0.226429 0.690144 0.042 Uiso 1 1 calc R U . . .
C3B C 0.7972(2) 0.3516(2) 0.83078(14) 0.0316(4) Uani 1 1 d . . . . .
H3B1 H 0.891359 0.313719 0.829890 0.047 Uiso 1 1 calc R U . . .
H3B2 H 0.819812 0.449283 0.865767 0.047 Uiso 1 1 calc R U . . .
H3B3 H 0.719140 0.309247 0.865247 0.047 Uiso 1 1 calc R U . . .
C4C C 0.5591(2) 0.71169(18) 0.88905(13) 0.0244(4) Uani 1 1 d . . . . .
C6C C 0.6980(2) 0.82761(18) 1.05178(13) 0.0253(4) Uani 1 1 d . . . . .
C7C C 0.7179(3) 0.96821(19) 1.04305(16) 0.0366(5) Uani 1 1 d . . . . .
H7C1 H 0.807139 1.025924 1.085714 0.055 Uiso 1 1 calc R U . . .
H7C2 H 0.734065 0.962194 0.973645 0.055 Uiso 1 1 calc R U . . .
H7C3 H 0.625357 1.007053 1.064175 0.055 Uiso 1 1 calc R U . . .
C8C C 0.6515(2) 0.8320(2) 1.15550(14) 0.0333(5) Uani 1 1 d . . . . .
H8C1 H 0.733091 0.890092 1.204869 0.050 Uiso 1 1 calc R U . . .
H8C2 H 0.555842 0.868305 1.169106 0.050 Uiso 1 1 calc R U . . .
H8C3 H 0.635770 0.740479 1.159434 0.050 Uiso 1 1 calc R U . . .
C9C C 0.8408(2) 0.7646(2) 1.02499(15) 0.0332(4) Uani 1 1 d . . . . .
H9C1 H 0.929471 0.824449 1.067039 0.050 Uiso 1 1 calc R U . . .
H9C2 H 0.825774 0.677040 1.035834 0.050 Uiso 1 1 calc R U . . .
H9C3 H 0.859458 0.751507 0.954777 0.050 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S14 C13 1.7143(18) . ?
S14 C15 1.7161(19) . ?
P1 O1 1.4744(12) . ?
P1 O1B 1.5673(12) . ?
P1 O1A 1.5767(13) . ?
P1 C2 1.8143(16) . ?
O10 C10 1.2272(19) . ?
O1A C2A 1.455(2) . ?
O1B C2B 1.455(2) . ?
O4C C4C 1.210(2) . ?
O5C C4C 1.346(2) . ?
O5C C6C 1.481(2) . ?
N4 C4C 1.366(2) . ?
N4 C5 1.466(2) . ?
N4 C3 1.472(2) . ?
N9 C10 1.354(2) . ?
N9 C2 1.458(2) . ?
C2 C3 1.557(2) . ?
C3 C8 1.534(2) . ?
C5 C6 1.518(2) . ?
C6 C7 1.527(2) . ?
C7 C8 1.525(3) . ?
C10 C11 1.519(2) . ?
C11 C12 1.511(2) . ?
C12 C13 1.358(2) . ?
C12 C16 1.424(2) . ?
C15 C16 1.363(2) . ?
C2A C3A 1.495(3) . ?
C2B C3B 1.494(3) . ?
C6C C9C 1.517(3) . ?
C6C C8C 1.519(3) . ?
C6C C7C 1.522(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 S14 C15 91.70(9) . . ?
O1 P1 O1B 116.56(7) . . ?
O1 P1 O1A 113.71(7) . . ?
O1B P1 O1A 102.74(6) . . ?
O1 P1 C2 113.40(7) . . ?
O1B P1 C2 103.06(7) . . ?
O1A P1 C2 106.06(7) . . ?
C2A O1A P1 122.35(11) . . ?
C2B O1B P1 118.99(11) . . ?
C4C O5C C6C 120.11(14) . . ?
C4C N4 C5 121.95(14) . . ?
C4C N4 C3 117.51(13) . . ?
C5 N4 C3 115.78(13) . . ?
C10 N9 C2 120.47(13) . . ?
N9 C2 C3 112.60(12) . . ?
N9 C2 P1 106.32(10) . . ?
C3 C2 P1 114.08(12) . . ?
N4 C3 C8 108.41(13) . . ?
N4 C3 C2 110.11(12) . . ?
C8 C3 C2 113.91(14) . . ?
N4 C5 C6 110.96(13) . . ?
C5 C6 C7 109.86(14) . . ?
C8 C7 C6 111.07(16) . . ?
C7 C8 C3 113.18(14) . . ?
O10 C10 N9 122.91(15) . . ?
O10 C10 C11 121.29(15) . . ?
N9 C10 C11 115.79(14) . . ?
C12 C11 C10 109.92(13) . . ?
C13 C12 C16 112.31(15) . . ?
C13 C12 C11 123.03(15) . . ?
C16 C12 C11 124.58(15) . . ?
C12 C13 S14 111.93(13) . . ?
C16 C15 S14 111.52(14) . . ?
C15 C16 C12 112.53(16) . . ?
O1A C2A C3A 110.53(16) . . ?
O1B C2B C3B 108.21(15) . . ?
O4C C4C O5C 124.95(16) . . ?
O4C C4C N4 123.46(16) . . ?
O5C C4C N4 111.59(15) . . ?
O5C C6C C9C 109.49(14) . . ?
O5C C6C C8C 102.05(15) . . ?
C9C C6C C8C 111.40(16) . . ?
O5C C6C C7C 111.11(15) . . ?
C9C C6C C7C 112.06(17) . . ?
C8C C6C C7C 110.30(16) . . ?

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
O1 P1 O1A C2A -30.85(15) . . . . ?
O1B P1 O1A C2A -157.72(13) . . . . ?
C2 P1 O1A C2A 94.45(14) . . . . ?
O1 P1 O1B C2B -57.72(16) . . . . ?
O1A P1 O1B C2B 67.30(15) . . . . ?
C2 P1 O1B C2B 177.40(14) . . . . ?
C10 N9 C2 C3 -115.56(16) . . . . ?
C10 N9 C2 P1 118.83(14) . . . . ?
O1 P1 C2 N9 66.39(12) . . . . ?
O1B P1 C2 N9 -166.70(10) . . . . ?
O1A P1 C2 N9 -59.10(11) . . . . ?
O1 P1 C2 C3 -58.32(13) . . . . ?
O1B P1 C2 C3 68.59(12) . . . . ?
O1A P1 C2 C3 176.19(10) . . . . ?
C4C N4 C3 C8 -101.30(18) . . . . ?
C5 N4 C3 C8 54.78(18) . . . . ?
C4C N4 C3 C2 133.48(16) . . . . ?
C5 N4 C3 C2 -70.45(17) . . . . ?
N9 C2 C3 N4 161.89(13) . . . . ?
P1 C2 C3 N4 -76.83(15) . . . . ?
N9 C2 C3 C8 39.86(19) . . . . ?
P1 C2 C3 C8 161.15(12) . . . . ?
C4C N4 C5 C6 96.77(19) . . . . ?
C3 N4 C5 C6 -58.15(18) . . . . ?
N4 C5 C6 C7 55.1(2) . . . . ?
C5 C6 C7 C8 -53.8(2) . . . . ?
C6 C7 C8 C3 53.6(2) . . . . ?
N4 C3 C8 C7 -51.78(19) . . . . ?
C2 C3 C8 C7 71.18(18) . . . . ?
C2 N9 C10 O10 3.0(2) . . . . ?
C2 N9 C10 C11 -175.77(13) . . . . ?
O10 C10 C11 C12 -78.66(19) . . . . ?
N9 C10 C11 C12 100.12(16) . . . . ?
C10 C11 C12 C13 -113.80(18) . . . . ?
C10 C11 C12 C16 62.4(2) . . . . ?
C16 C12 C13 S14 -0.38(19) . . . . ?
C11 C12 C13 S14 176.24(12) . . . . ?
C15 S14 C13 C12 0.19(14) . . . . ?
C13 S14 C15 C16 0.06(15) . . . . ?
S14 C15 C16 C12 -0.3(2) . . . . ?
C13 C12 C16 C15 0.4(2) . . . . ?
C11 C12 C16 C15 -176.12(16) . . . . ?
P1 O1A C2A C3A 106.95(16) . . . . ?
P1 O1B C2B C3B 170.15(13) . . . . ?
C6C O5C C4C O4C -5.4(3) . . . . ?
C6C O5C C4C N4 174.57(14) . . . . ?
C5 N4 C4C O4C -172.93(17) . . . . ?
C3 N4 C4C O4C -18.4(3) . . . . ?
C5 N4 C4C O5C 7.1(2) . . . . ?
C3 N4 C4C O5C 161.61(14) . . . . ?
C4C O5C C6C C9C -64.4(2) . . . . ?
C4C O5C C6C C8C 177.51(15) . . . . ?
C4C O5C C6C C7C 59.9(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N9 H9 O1 0.876(14) 1.987(14) 2.8617(18) 176.1(18) 2_666 yes

_refine_diff_density_max         0.395
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_4l-1
_database_code_depnum_ccdc_archive 'CCDC 2203669'
loop_
_audit_author_name
_audit_author_address
'Arto Valkonen'
;University of Jyvaskyla
Finland
;
_audit_update_record             
;
2022-08-26 deposited with the CCDC.	2023-08-01 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H37 N2 O6 P S'
_chemical_formula_sum            'C25 H37 N2 O6 P S'
_chemical_formula_weight         524.59

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   9.3831(3)
_cell_length_b                   26.8231(6)
_cell_length_c                   11.5306(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.972(3)
_cell_angle_gamma                90
_cell_volume                     2760.47(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    4841
_cell_measurement_theta_min      2.3930
_cell_measurement_theta_max      29.5710

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_F_000             1120
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.215
_shelx_estimated_absorpt_T_min   0.921
_shelx_estimated_absorpt_T_max   0.962
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_T_max  0.974
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'SuperNova, Single source at offset/far, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.0107
_diffrn_reflns_number            13222
_diffrn_reflns_av_unetI/netI     0.0452
_diffrn_reflns_av_R_equivalents  0.0252
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -34
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.006
_diffrn_reflns_theta_max         29.848
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.875
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.875
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.875
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6953
_reflns_number_gt                5464
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    SHELXL-2018/3
_computing_publication_material  SHELXL-2018/3
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0350P)²+1.1442P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6953
_refine_ls_number_parameters     389
_refine_ls_number_restraints     66
_refine_ls_R_factor_all          0.0632
_refine_ls_R_factor_gt           0.0464
_refine_ls_wR_factor_ref         0.1110
_refine_ls_wR_factor_gt          0.1011
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.062
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S14 S 0.10694(7) 0.29621(2) 0.00437(6) 0.03841(19) Uani 0.8923(19) 1 d D . P A
1
S14D S 0.4759(9) 0.3752(3) 0.0351(9) 0.047(2) Uani 0.1077(19) 1 d D U P A 2
P1 P 0.24699(5) 0.53253(2) 0.51530(4) 0.02161(11) Uani 1 1 d . . . . .
O1 O 0.40093(13) 0.54233(5) 0.59353(10) 0.0261(3) Uani 1 1 d . . . . .
O10 O 0.06700(14) 0.42678(5) 0.25746(12) 0.0313(3) Uani 1 1 d . . . . .
O1A O 0.16131(13) 0.49319(5) 0.56955(10) 0.0287(3) Uani 1 1 d . . . . .
O1B O 0.13974(14) 0.57880(5) 0.48547(11) 0.0293(3) Uani 1 1 d . . . . .
O4C O 0.49100(14) 0.62559(5) 0.40327(11) 0.0309(3) Uani 1 1 d . . . . .
O5C O 0.29444(15) 0.67656(4) 0.31271(11) 0.0312(3) Uani 1 1 d . . . . .
N4 N 0.26723(16) 0.59448(5) 0.28594(12) 0.0229(3) Uani 1 1 d . . . . .
N9 N 0.28822(16) 0.45927(5) 0.37323(13) 0.0216(3) Uani 1 1 d D . . . .
H9 H 0.3840(16) 0.4561(7) 0.4014(16) 0.026 Uiso 1 1 d D U . . .
C2 C 0.23382(18) 0.51029(6) 0.36375(14) 0.0203(3) Uani 1 1 d . . . . .
H2 H 0.126056 0.510518 0.312967 0.024 Uiso 1 1 calc R U . . .
C3 C 0.32346(18) 0.54330(6) 0.30039(14) 0.0209(3) Uani 1 1 d . . . . .
H3 H 0.430198 0.544041 0.353496 0.025 Uiso 1 1 calc R U . . .
C5 C 0.1176(2) 0.60183(7) 0.19931(15) 0.0273(4) Uani 1 1 d . . . . .
H5A H 0.092397 0.637771 0.193880 0.033 Uiso 1 1 calc R U . . .
H5B H 0.042797 0.584018 0.228471 0.033 Uiso 1 1 calc R U . . .
C6 C 0.1113(2) 0.58243(7) 0.07377(16) 0.0327(4) Uani 1 1 d . . . . .
H6A H 0.174895 0.603552 0.039364 0.039 Uiso 1 1 calc R U . . .
H6B H 0.007105 0.584356 0.018591 0.039 Uiso 1 1 calc R U . . .
C7 C 0.1658(2) 0.52850(7) 0.08167(15) 0.0305(4) Uani 1 1 d . . . . .
H7A H 0.093696 0.506677 0.104500 0.037 Uiso 1 1 calc R U . . .
H7B H 0.170411 0.517696 0.000802 0.037 Uiso 1 1 calc R U . . .
C8 C 0.3201(2) 0.52301(7) 0.17541(15) 0.0266(4) Uani 1 1 d . . . . .
H8A H 0.394645 0.541160 0.146593 0.032 Uiso 1 1 calc R U . . .
H8B H 0.348579 0.487344 0.183366 0.032 Uiso 1 1 calc R U . . .
C10 C 0.20021(19) 0.42170(6) 0.31289(14) 0.0221(3) Uani 1 1 d . . . . .
C11 C 0.2792(2) 0.37185(6) 0.32025(15) 0.0267(4) Uani 1 1 d D . . . .
H11A H 0.388896 0.376973 0.352038 0.032 Uiso 0.8923(19) 1 calc R U P A 1
H11B H 0.249637 0.349742 0.377666 0.032 Uiso 0.8923(19) 1 calc R U P A 1
H11C H 0.209907 0.344463 0.323762 0.032 Uiso 0.1077(19) 1 calc R U P A 2
H11D H 0.366533 0.370464 0.395002 0.032 Uiso 0.1077(19) 1 calc R U P A 2
C12 C 0.2404(2) 0.34741(7) 0.19769(17) 0.0236(4) Uani 0.8923(19) 1 d D . P A 1
C13 C 0.1267(2) 0.31535(8) 0.1517(2) 0.0322(5) Uani 0.8923(19) 1 d D . P A 1
H13 H 0.062842 0.304204 0.196310 0.039 Uiso 0.8923(19) 1 calc R U P A 1
C15 C 0.2578(3) 0.33278(8) 0.0003(2) 0.0300(5) Uani 0.8923(19) 1 d D . P A 1
C16 C 0.3168(3) 0.33756(8) -0.09661(19) 0.0389(6) Uani 0.8923(19) 1 d . . P A 1
H16 H 0.272523 0.320840 -0.171765 0.047 Uiso 0.8923(19) 1 calc R U P A 1
C17 C 0.4410(3) 0.36722(9) -0.0796(2) 0.0435(6) Uani 0.8923(19) 1 d . . P A 1
H17 H 0.483341 0.370829 -0.144103 0.052 Uiso 0.8923(19) 1 calc R U P A 1
C18 C 0.5067(5) 0.39232(12) 0.0309(4) 0.0356(8) Uani 0.8923(19) 1 d . . P A 1
H18 H 0.593124 0.412332 0.040569 0.043 Uiso 0.8923(19) 1 calc R U P A 1
C19 C 0.4464(3) 0.38808(9) 0.1255(2) 0.0285(5) Uani 0.8923(19) 1 d . . P A 1
H19 H 0.490597 0.405348 0.199841 0.034 Uiso 0.8923(19) 1 calc R U P A 1
C20 C 0.3192(2) 0.35804(7) 0.11120(18) 0.0241(4) Uani 0.8923(19) 1 d D . P A 1
C12D C 0.3341(19) 0.3654(7) 0.2010(13) 0.043(4) Uani 0.1077(19) 1 d D U P A 2
C13D C 0.458(3) 0.3865(9) 0.1782(17) 0.041(4) Uani 0.1077(19) 1 d D U P A 2
H13D H 0.529627 0.405845 0.237553 0.049 Uiso 0.1077(19) 1 calc R U P A 2
C15D C 0.3078(14) 0.3407(6) -0.0036(15) 0.049(4) Uani 0.1077(19) 1 d DG U P A 2
C16D C 0.2364(17) 0.3160(6) -0.1119(12) 0.056(4) Uani 0.1077(19) 1 d G U P A 2
H16D H 0.278533 0.316483 -0.177004 0.067 Uiso 0.1077(19) 1 calc R U P A 2
C17D C 0.1034(16) 0.2905(6) -0.1249(12) 0.060(5) Uani 0.1077(19) 1 d G U P A 2
H17D H 0.054615 0.273567 -0.198942 0.071 Uiso 0.1077(19) 1 calc R U P A 2
C18D C 0.0418(14) 0.2897(5) -0.0297(15) 0.052(4) Uani 0.1077(19) 1 d G U P A 2
H18D H -0.049093 0.272322 -0.038619 0.062 Uiso 0.1077(19) 1 calc R U P A 2
C19D C 0.1132(16) 0.3145(5) 0.0786(12) 0.034(3) Uani 0.1077(19) 1 d G U P A 2
H19D H 0.071118 0.313994 0.143645 0.041 Uiso 0.1077(19) 1 calc R U P A 2
C20D C 0.2462(15) 0.3400(5) 0.0916(12) 0.047(4) Uani 0.1077(19) 1 d DG U P A 2
C2A C 0.2325(2) 0.46083(7) 0.67069(16) 0.0298(4) Uani 1 1 d . . . . .
H2A H 0.332025 0.450582 0.666218 0.036 Uiso 1 1 calc R U . . .
H2B H 0.171099 0.430425 0.665847 0.036 Uiso 1 1 calc R U . . .
C3A C 0.2505(2) 0.48671(8) 0.78920(17) 0.0370(5) Uani 1 1 d . . . . .
H3A H 0.299028 0.464157 0.856714 0.055 Uiso 1 1 calc R U . . .
H3B H 0.312553 0.516531 0.794465 0.055 Uiso 1 1 calc R U . . .
H3C H 0.151858 0.496403 0.794095 0.055 Uiso 1 1 calc R U . . .
C2B C 0.1402(2) 0.61545(7) 0.57801(17) 0.0333(4) Uani 1 1 d . . . . .
H2C H 0.241063 0.630431 0.611433 0.040 Uiso 1 1 calc R U . . .
H2D H 0.112597 0.599643 0.645653 0.040 Uiso 1 1 calc R U . . .
C3B C 0.0277(3) 0.65465(8) 0.5178(2) 0.0474(6) Uani 1 1 d . . . . .
H3D H 0.024742 0.680228 0.577646 0.071 Uiso 1 1 calc R U . . .
H3E H 0.056420 0.669991 0.451085 0.071 Uiso 1 1 calc R U . . .
H3F H -0.071469 0.639341 0.485151 0.071 Uiso 1 1 calc R U . . .
C4C C 0.3624(2) 0.63177(6) 0.33979(14) 0.0236(4) Uani 1 1 d . . . . .
C6C C 0.3778(2) 0.72267(7) 0.35903(17) 0.0326(4) Uani 1 1 d . . . . .
C7C C 0.5152(3) 0.72704(7) 0.31722(18) 0.0397(5) Uani 1 1 d . . . . .
H7C H 0.568675 0.757943 0.349139 0.060 Uiso 1 1 calc R U . . .
H7D H 0.581326 0.698465 0.347532 0.060 Uiso 1 1 calc R U . . .
H7E H 0.484612 0.727528 0.227920 0.060 Uiso 1 1 calc R U . . .
C8C C 0.2640(3) 0.76228(8) 0.2989(2) 0.0519(6) Uani 1 1 d . . . . .
H8C H 0.307226 0.795364 0.323187 0.078 Uiso 1 1 calc R U . . .
H8D H 0.236806 0.758917 0.210096 0.078 Uiso 1 1 calc R U . . .
H8E H 0.174324 0.758191 0.324487 0.078 Uiso 1 1 calc R U . . .
C9C C 0.4167(3) 0.72470(8) 0.49667(18) 0.0471(6) Uani 1 1 d . . . . .
H9C H 0.472091 0.755437 0.526979 0.071 Uiso 1 1 calc R U . . .
H9D H 0.324317 0.724130 0.519456 0.071 Uiso 1 1 calc R U . . .
H9E H 0.478663 0.695839 0.532559 0.071 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S14 C13 1.729(2) . ?
S14 C15 1.735(3) . ?
S14D C13D 1.733(16) . ?
S14D C15D 1.763(11) . ?
P1 O1 1.4714(12) . ?
P1 O1B 1.5678(13) . ?
P1 O1A 1.5689(13) . ?
P1 C2 1.8142(16) . ?
O10 C10 1.223(2) . ?
O1A C2A 1.442(2) . ?
O1B C2B 1.450(2) . ?
O4C C4C 1.214(2) . ?
O5C C4C 1.351(2) . ?
O5C C6C 1.473(2) . ?
N4 C4C 1.357(2) . ?
N4 C3 1.462(2) . ?
N4 C5 1.464(2) . ?
N9 C10 1.352(2) . ?
N9 C2 1.453(2) . ?
C2 C3 1.551(2) . ?
C3 C8 1.532(2) . ?
C5 C6 1.522(2) . ?
C6 C7 1.527(3) . ?
C7 C8 1.523(3) . ?
C10 C11 1.518(2) . ?
C11 C12 1.497(2) . ?
C11 C12D 1.620(14) . ?
C12 C13 1.345(3) . ?
C12 C20 1.441(3) . ?
C15 C16 1.397(3) . ?
C15 C20 1.404(3) . ?
C16 C17 1.374(4) . ?
C17 C18 1.405(5) . ?
C18 C19 1.379(4) . ?
C19 C20 1.407(3) . ?
C12D C13D 1.393(17) . ?
C12D C20D 1.447(15) . ?
C15D C16D 1.3900 . ?
C15D C20D 1.3900 . ?
C16D C17D 1.3900 . ?
C17D C18D 1.3900 . ?
C18D C19D 1.3900 . ?
C19D C20D 1.3900 . ?
C2A C3A 1.495(3) . ?
C2B C3B 1.500(3) . ?
C6C C7C 1.514(3) . ?
C6C C8C 1.514(3) . ?
C6C C9C 1.516(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 S14 C15 91.03(11) . . ?
C13D S14D C15D 89.6(10) . . ?
O1 P1 O1B 115.80(7) . . ?
O1 P1 O1A 113.75(7) . . ?
O1B P1 O1A 104.29(7) . . ?
O1 P1 C2 114.29(7) . . ?
O1B P1 C2 101.57(7) . . ?
O1A P1 C2 105.78(7) . . ?
C2A O1A P1 124.12(11) . . ?
C2B O1B P1 121.28(11) . . ?
C4C O5C C6C 120.20(14) . . ?
C4C N4 C3 118.47(14) . . ?
C4C N4 C5 124.77(15) . . ?
C3 N4 C5 116.15(13) . . ?
C10 N9 C2 121.26(14) . . ?
N9 C2 C3 110.14(13) . . ?
N9 C2 P1 108.62(11) . . ?
C3 C2 P1 112.36(11) . . ?
N4 C3 C8 108.94(13) . . ?
N4 C3 C2 111.15(13) . . ?
C8 C3 C2 112.57(13) . . ?
N4 C5 C6 110.53(15) . . ?
C5 C6 C7 110.68(14) . . ?
C8 C7 C6 111.18(15) . . ?
C7 C8 C3 111.87(14) . . ?
O10 C10 N9 123.32(16) . . ?
O10 C10 C11 121.99(15) . . ?
N9 C10 C11 114.69(15) . . ?
C12 C11 C10 111.13(14) . . ?
C10 C11 C12D 108.9(7) . . ?
C13 C12 C20 111.57(18) . . ?
C13 C12 C11 125.72(19) . . ?
C20 C12 C11 122.64(17) . . ?
C12 C13 S14 114.10(17) . . ?
C16 C15 C20 122.1(2) . . ?
C16 C15 S14 126.99(18) . . ?
C20 C15 S14 110.92(17) . . ?
C17 C16 C15 117.8(2) . . ?
C16 C17 C18 121.5(2) . . ?
C19 C18 C17 120.4(3) . . ?
C18 C19 C20 119.7(3) . . ?
C15 C20 C19 118.5(2) . . ?
C15 C20 C12 112.38(19) . . ?
C19 C20 C12 129.06(19) . . ?
C13D C12D C20D 108.2(14) . . ?
C13D C12D C11 128.4(13) . . ?
C20D C12D C11 123.0(13) . . ?
C12D C13D S14D 116.1(15) . . ?
C16D C15D C20D 120.0 . . ?
C16D C15D S14D 128.6(10) . . ?
C20D C15D S14D 111.4(10) . . ?
C15D C16D C17D 120.0 . . ?
C16D C17D C18D 120.0 . . ?
C19D C18D C17D 120.0 . . ?
C20D C19D C18D 120.0 . . ?
C19D C20D C15D 120.0 . . ?
C19D C20D C12D 125.3(12) . . ?
C15D C20D C12D 114.7(12) . . ?
O1A C2A C3A 110.69(16) . . ?
O1B C2B C3B 107.00(15) . . ?
O4C C4C O5C 124.84(16) . . ?
O4C C4C N4 124.51(16) . . ?
O5C C4C N4 110.65(15) . . ?
O5C C6C C7C 111.03(15) . . ?
O5C C6C C8C 101.68(16) . . ?
C7C C6C C8C 110.45(17) . . ?
O5C C6C C9C 109.82(15) . . ?
C7C C6C C9C 112.17(18) . . ?
C8C C6C C9C 111.22(17) . . ?

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
O1 P1 O1A C2A -13.70(15) . . . . ?
O1B P1 O1A C2A -140.77(13) . . . . ?
C2 P1 O1A C2A 112.55(13) . . . . ?
O1 P1 O1B C2B -41.31(15) . . . . ?
O1A P1 O1B C2B 84.47(14) . . . . ?
C2 P1 O1B C2B -165.75(13) . . . . ?
C10 N9 C2 C3 -114.96(16) . . . . ?
C10 N9 C2 P1 121.60(14) . . . . ?
O1 P1 C2 N9 72.15(13) . . . . ?
O1B P1 C2 N9 -162.41(11) . . . . ?
O1A P1 C2 N9 -53.77(12) . . . . ?
O1 P1 C2 C3 -49.95(14) . . . . ?
O1B P1 C2 C3 75.49(12) . . . . ?
O1A P1 C2 C3 -175.87(11) . . . . ?
C4C N4 C3 C8 -115.45(16) . . . . ?
C5 N4 C3 C8 56.03(18) . . . . ?
C4C N4 C3 C2 119.96(15) . . . . ?
C5 N4 C3 C2 -68.56(17) . . . . ?
N9 C2 C3 N4 178.01(12) . . . . ?
P1 C2 C3 N4 -60.76(15) . . . . ?
N9 C2 C3 C8 55.49(18) . . . . ?
P1 C2 C3 C8 176.73(11) . . . . ?
C4C N4 C5 C6 114.10(18) . . . . ?
C3 N4 C5 C6 -56.78(19) . . . . ?
N4 C5 C6 C7 53.2(2) . . . . ?
C5 C6 C7 C8 -53.5(2) . . . . ?
C6 C7 C8 C3 54.3(2) . . . . ?
N4 C3 C8 C7 -53.41(19) . . . . ?
C2 C3 C8 C7 70.34(19) . . . . ?
C2 N9 C10 O10 -7.7(2) . . . . ?
C2 N9 C10 C11 173.08(14) . . . . ?
O10 C10 C11 C12 46.3(2) . . . . ?
N9 C10 C11 C12 -134.46(16) . . . . ?
O10 C10 C11 C12D 85.6(7) . . . . ?
N9 C10 C11 C12D -95.2(7) . . . . ?
C10 C11 C12 C13 -91.2(2) . . . . ?
C10 C11 C12 C20 85.5(2) . . . . ?
C20 C12 C13 S14 -0.1(2) . . . . ?
C11 C12 C13 S14 177.00(15) . . . . ?
C15 S14 C13 C12 -0.26(18) . . . . ?
C13 S14 C15 C16 179.7(2) . . . . ?
C13 S14 C15 C20 0.51(17) . . . . ?
C20 C15 C16 C17 1.5(3) . . . . ?
S14 C15 C16 C17 -177.60(19) . . . . ?
C15 C16 C17 C18 -0.4(4) . . . . ?
C16 C17 C18 C19 -0.6(5) . . . . ?
C17 C18 C19 C20 0.6(5) . . . . ?
C16 C15 C20 C19 -1.6(3) . . . . ?
S14 C15 C20 C19 177.67(17) . . . . ?
C16 C15 C20 C12 -179.9(2) . . . . ?
S14 C15 C20 C12 -0.6(2) . . . . ?
C18 C19 C20 C15 0.5(4) . . . . ?
C18 C19 C20 C12 178.5(3) . . . . ?
C13 C12 C20 C15 0.5(3) . . . . ?
C11 C12 C20 C15 -176.70(18) . . . . ?
C13 C12 C20 C19 -177.6(2) . . . . ?
C11 C12 C20 C19 5.2(3) . . . . ?
C10 C11 C12D C13D 79(2) . . . . ?
C10 C11 C12D C20D -93.8(15) . . . . ?
C20D C12D C13D S14D -2(2) . . . . ?
C11 C12D C13D S14D -175.3(13) . . . . ?
C15D S14D C13D C12D 0.7(19) . . . . ?
C13D S14D C15D C16D -179.0(13) . . . . ?
C13D S14D C15D C20D 0.9(12) . . . . ?
C20D C15D C16D C17D 0.0 . . . . ?
S14D C15D C16D C17D 179.8(15) . . . . ?
C15D C16D C17D C18D 0.0 . . . . ?
C16D C17D C18D C19D 0.0 . . . . ?
C17D C18D C19D C20D 0.0 . . . . ?
C18D C19D C20D C15D 0.0 . . . . ?
C18D C19D C20D C12D -177.4(16) . . . . ?
C16D C15D C20D C19D 0.0 . . . . ?
S14D C15D C20D C19D -179.9(13) . . . . ?
C16D C15D C20D C12D 177.6(14) . . . . ?
S14D C15D C20D C12D -2.2(13) . . . . ?
C13D C12D C20D C19D -179.8(15) . . . . ?
C11 C12D C20D C19D -6(2) . . . . ?
C13D C12D C20D C15D 3(2) . . . . ?
C11 C12D C20D C15D 176.4(11) . . . . ?
P1 O1A C2A C3A 84.55(17) . . . . ?
P1 O1B C2B C3B 178.75(14) . . . . ?
C6C O5C C4C O4C 1.3(2) . . . . ?
C6C O5C C4C N4 -178.53(14) . . . . ?
C3 N4 C4C O4C -2.6(2) . . . . ?
C5 N4 C4C O4C -173.30(16) . . . . ?
C3 N4 C4C O5C 177.22(13) . . . . ?
C5 N4 C4C O5C 6.5(2) . . . . ?
C4C O5C C6C C7C 58.2(2) . . . . ?
C4C O5C C6C C8C 175.65(16) . . . . ?
C4C O5C C6C C9C -66.5(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N9 H9 O1 0.860(14) 2.001(15) 2.8225(18) 159.4(17) 3_666 yes

_refine_diff_density_max         0.376
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.050

