# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2017

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

data_3
_database_code_depnum_ccdc_archive 'CCDC 1510998'
_audit_update_record             
;
2016-12-19 deposited with the CCDC.
2017-01-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H20 N O4 P, C12 H8 N2, H2 O'
_chemical_formula_sum            'C24 H30 N3 O5 P'
_chemical_formula_weight         471.48

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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                   10.5437(3)
_cell_length_b                   10.6658(4)
_cell_length_c                   11.1228(4)
_cell_angle_alpha                86.656(3)
_cell_angle_beta                 71.241(3)
_cell_angle_gamma                82.672(3)
_cell_volume                     1174.52(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    10851
_cell_measurement_theta_min      2.1040
_cell_measurement_theta_max      31.1870

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_F_000             500
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.158
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7263
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            13007
_diffrn_reflns_av_unetI/netI     0.0772
_diffrn_reflns_av_R_equivalents  0.1187
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.332
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4117
_reflns_number_gt                3588
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_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)+(0.1433P)²+0.4793P] 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         4117
_refine_ls_number_parameters     319
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0751
_refine_ls_wR_factor_ref         0.2047
_refine_ls_wR_factor_gt          0.1925
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.070
_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
P1 P 0.31829(5) 0.52141(5) 0.15361(5) 0.0156(3) Uani 1 1 d . . . . .
O1 O 0.36161(15) 0.46726(14) 0.27572(15) 0.0166(4) Uani 1 1 d . U . . .
O4 O 0.40461(16) 0.63346(15) 0.10072(16) 0.0195(4) Uani 1 1 d . . . . .
H4 H 0.4780 0.6062 0.0513 0.029 Uiso 1 1 calc R U . . .
O2 O 0.36138(16) 0.41609(16) 0.06012(16) 0.0195(4) Uani 1 1 d . . . . .
N1 N 0.05240(19) 0.52710(19) 0.78725(19) 0.0182(5) Uani 1 1 d . . . . .
H1A H -0.0301 0.5068 0.7990 0.022 Uiso 1 1 calc R U . . .
H1B H 0.0470 0.6065 0.8106 0.022 Uiso 1 1 calc R U . . .
H1C H 0.0919 0.4755 0.8338 0.022 Uiso 1 1 calc R U . . .
O3 O 0.17288(16) 0.57289(16) 0.19700(16) 0.0211(4) Uani 1 1 d . . . . .
C2 C 0.2010(2) 0.3924(2) 0.4629(2) 0.0159(5) Uani 1 1 d . . . . .
C10 C 0.3792(2) 0.6943(2) 0.3932(2) 0.0196(5) Uani 1 1 d . . . . .
H10 H 0.3651 0.7103 0.3105 0.024 Uiso 1 1 calc R U . . .
C3 C 0.1248(2) 0.4091(2) 0.5897(2) 0.0167(5) Uani 1 1 d . . . . .
H3 H 0.0687 0.3492 0.6324 0.020 Uiso 1 1 calc R U . . .
C1 C 0.2811(2) 0.4871(2) 0.4011(2) 0.0161(5) Uani 1 1 d . . . . .
C5 C 0.2131(2) 0.6062(2) 0.5907(2) 0.0175(5) Uani 1 1 d . . . . .
C6 C 0.2884(2) 0.5950(2) 0.4630(2) 0.0164(5) Uani 1 1 d . . . . .
C4 C 0.1322(2) 0.5148(2) 0.6524(2) 0.0171(5) Uani 1 1 d . . . . .
C9 C 0.0809(3) 0.2020(2) 0.4507(3) 0.0256(6) Uani 1 1 d . . . . .
H9A H 0.0777 0.1683 0.5334 0.038 Uiso 1 1 calc R U . . .
H9B H 0.0849 0.1342 0.3960 0.038 Uiso 1 1 calc R U . . .
H9C H 0.0016 0.2600 0.4573 0.038 Uiso 1 1 calc R U . . .
C7 C 0.2056(2) 0.2710(2) 0.3956(2) 0.0190(5) Uani 1 1 d . . . . .
H7 H 0.2150 0.2924 0.3065 0.023 Uiso 1 1 calc R U . . .
C11 C 0.3467(3) 0.8200(3) 0.4605(3) 0.0313(6) Uani 1 1 d . . . . .
H11A H 0.2537 0.8511 0.4742 0.047 Uiso 1 1 calc R U . . .
H11B H 0.4029 0.8798 0.4091 0.047 Uiso 1 1 calc R U . . .
H11C H 0.3629 0.8084 0.5408 0.047 Uiso 1 1 calc R U . . .
C12 C 0.5276(3) 0.6433(3) 0.3679(3) 0.0309(7) Uani 1 1 d . . . . .
H12A H 0.5452 0.6271 0.4472 0.046 Uiso 1 1 calc R U . . .
H12B H 0.5836 0.7045 0.3189 0.046 Uiso 1 1 calc R U . . .
H12C H 0.5472 0.5662 0.3216 0.046 Uiso 1 1 calc R U . . .
C8 C 0.3313(3) 0.1832(3) 0.3997(3) 0.0285(6) Uani 1 1 d . . . . .
H8A H 0.4096 0.2272 0.3657 0.043 Uiso 1 1 calc R U . . .
H8B H 0.3409 0.1100 0.3499 0.043 Uiso 1 1 calc R U . . .
H8C H 0.3221 0.1575 0.4859 0.043 Uiso 1 1 calc R U . . .
N2 N 0.1327(2) 0.1624(2) 0.1123(2) 0.0236(5) Uani 1 1 d . . . . .
N3 N -0.1281(2) 0.24731(19) 0.1232(2) 0.0232(5) Uani 1 1 d . . . . .
C17 C 0.0399(3) 0.0781(2) 0.1403(2) 0.0221(6) Uani 1 1 d . . . . .
C18 C -0.0969(3) 0.1225(2) 0.1458(2) 0.0217(6) Uani 1 1 d . . . . .
C16 C 0.0751(3) -0.0522(2) 0.1615(2) 0.0263(6) Uani 1 1 d . . . . .
C20 C -0.1526(3) -0.0967(3) 0.1920(3) 0.0309(7) Uani 1 1 d . . . . .
H20 H -0.2159 -0.1541 0.2098 0.037 Uiso 1 1 calc R U . . .
C13 C 0.2580(3) 0.1195(3) 0.1067(3) 0.0285(6) Uani 1 1 d . . . . .
C22 C -0.3244(3) 0.0822(3) 0.1760(3) 0.0314(7) Uani 1 1 d . . . . .
H22 H -0.3913 0.0283 0.1964 0.038 Uiso 1 1 calc R U . . .
C21 C -0.0251(3) -0.1378(2) 0.1852(2) 0.0309(7) Uani 1 1 d . . . . .
H21 H -0.0010 -0.2237 0.1959 0.037 Uiso 1 1 calc R U . . .
C24 C -0.2522(3) 0.2861(3) 0.1240(2) 0.0261(6) Uani 1 1 d . . . . .
H24 H -0.2729 0.3711 0.1062 0.031 Uiso 1 1 calc R U . . .
C14 C 0.2999(3) -0.0070(3) 0.1295(3) 0.0319(6) Uani 1 1 d . . . . .
H14 H 0.3886 -0.0322 0.1266 0.038 Uiso 1 1 calc R U . . .
C15 C 0.2083(3) -0.0932(3) 0.1563(3) 0.0321(7) Uani 1 1 d . . . . .
H15 H 0.2342 -0.1779 0.1708 0.039 Uiso 1 1 calc R U . . .
C23 C -0.3551(3) 0.2074(3) 0.1499(3) 0.0316(6) Uani 1 1 d . . . . .
H23 H -0.4413 0.2391 0.1493 0.038 Uiso 1 1 calc R U . . .
C19 C -0.1933(3) 0.0351(2) 0.1724(3) 0.0244(6) Uani 1 1 d . U . . .
O5 O 0.1679(2) 0.37931(17) 0.94527(18) 0.0262(5) Uani 1 1 d G . . . .
H5A H 0.1346 0.3167 0.9895 0.039 Uiso 1 1 d G U . . .
H5B H 0.229(4) 0.394(3) 0.966(4) 0.042(10) Uiso 1 1 d . . . . .
H5 H 0.218(2) 0.677(2) 0.634(3) 0.008(6) Uiso 1 1 d . . . . .
H13 H 0.325(4) 0.180(4) 0.083(4) 0.055(11) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O3 1.4917(17) . ?
P1 O2 1.5006(18) . ?
P1 O4 1.5664(16) . ?
P1 O1 1.6209(16) . ?
O1 C1 1.392(3) . ?
O4 H4 0.8200 . ?
N1 C4 1.469(3) . ?
N1 H1A 0.8900 . ?
N1 H1B 0.8900 . ?
N1 H1C 0.8900 . ?
C2 C3 1.390(3) . ?
C2 C1 1.403(3) . ?
C2 C7 1.520(3) . ?
C10 C11 1.520(4) . ?
C10 C6 1.525(3) . ?
C10 C12 1.530(3) . ?
C10 H10 0.9800 . ?
C3 C4 1.383(3) . ?
C3 H3 0.9300 . ?
C1 C6 1.398(3) . ?
C5 C4 1.381(3) . ?
C5 C6 1.390(3) . ?
C5 H5 0.93(3) . ?
C9 C7 1.524(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C7 C8 1.534(3) . ?
C7 H7 0.9800 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
N2 C13 1.325(4) . ?
N2 C17 1.363(3) . ?
N3 C24 1.319(3) . ?
N3 C18 1.358(3) . ?
C17 C16 1.419(4) . ?
C17 C18 1.442(4) . ?
C18 C19 1.417(3) . ?
C16 C15 1.400(4) . ?
C16 C21 1.434(4) . ?
C20 C21 1.339(4) . ?
C20 C19 1.442(4) . ?
C20 H20 0.9300 . ?
C13 C14 1.401(4) . ?
C13 H13 0.98(4) . ?
C22 C23 1.370(4) . ?
C22 C19 1.398(4) . ?
C22 H22 0.9300 . ?
C21 H21 0.9300 . ?
C24 C23 1.403(4) . ?
C24 H24 0.9300 . ?
C14 C15 1.370(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C23 H23 0.9300 . ?
O5 H5A 0.8498 . ?
O5 H5B 0.79(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
O3 P1 O2 117.84(10) . . ?
O3 P1 O4 108.64(9) . . ?
O2 P1 O4 109.97(9) . . ?
O3 P1 O1 109.03(9) . . ?
O2 P1 O1 105.83(9) . . ?
O4 P1 O1 104.73(9) . . ?
C1 O1 P1 124.02(14) . . ?
P1 O4 H4 109.5 . . ?
C4 N1 H1A 109.5 . . ?
C4 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C4 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C3 C2 C1 118.0(2) . . ?
C3 C2 C7 121.0(2) . . ?
C1 C2 C7 120.8(2) . . ?
C11 C10 C6 113.6(2) . . ?
C11 C10 C12 110.7(2) . . ?
C6 C10 C12 110.45(19) . . ?
C11 C10 H10 107.2 . . ?
C6 C10 H10 107.2 . . ?
C12 C10 H10 107.2 . . ?
C4 C3 C2 120.1(2) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
O1 C1 C6 119.7(2) . . ?
O1 C1 C2 117.7(2) . . ?
C6 C1 C2 122.4(2) . . ?
C4 C5 C6 120.7(2) . . ?
C4 C5 H5 120.5(16) . . ?
C6 C5 H5 118.8(16) . . ?
C5 C6 C1 117.6(2) . . ?
C5 C6 C10 121.6(2) . . ?
C1 C6 C10 120.8(2) . . ?
C5 C4 C3 121.2(2) . . ?
C5 C4 N1 120.6(2) . . ?
C3 C4 N1 118.3(2) . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C7 C9 114.4(2) . . ?
C2 C7 C8 108.46(19) . . ?
C9 C7 C8 109.7(2) . . ?
C2 C7 H7 108.1 . . ?
C9 C7 H7 108.1 . . ?
C8 C7 H7 108.1 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C13 N2 C17 118.0(2) . . ?
C24 N3 C18 117.9(2) . . ?
N2 C17 C16 121.7(2) . . ?
N2 C17 C18 119.0(2) . . ?
C16 C17 C18 119.3(2) . . ?
N3 C18 C19 122.2(2) . . ?
N3 C18 C17 118.4(2) . . ?
C19 C18 C17 119.3(2) . . ?
C15 C16 C17 118.4(2) . . ?
C15 C16 C21 122.2(2) . . ?
C17 C16 C21 119.5(3) . . ?
C21 C20 C19 121.1(2) . . ?
C21 C20 H20 119.5 . . ?
C19 C20 H20 119.5 . . ?
N2 C13 C14 123.7(3) . . ?
N2 C13 H13 117(2) . . ?
C14 C13 H13 119(2) . . ?
C23 C22 C19 120.4(3) . . ?
C23 C22 H22 119.8 . . ?
C19 C22 H22 119.8 . . ?
C20 C21 C16 121.4(2) . . ?
C20 C21 H21 119.3 . . ?
C16 C21 H21 119.3 . . ?
N3 C24 C23 124.2(3) . . ?
N3 C24 H24 117.9 . . ?
C23 C24 H24 117.9 . . ?
C15 C14 C13 119.0(3) . . ?
C15 C14 H14 120.5 . . ?
C13 C14 H14 120.5 . . ?
C14 C15 C16 119.2(2) . . ?
C14 C15 H15 120.4 . . ?
C16 C15 H15 120.4 . . ?
C22 C23 C24 117.8(3) . . ?
C22 C23 H23 121.1 . . ?
C24 C23 H23 121.1 . . ?
C22 C19 C18 117.3(2) . . ?
C22 C19 C20 123.2(2) . . ?
C18 C19 C20 119.4(2) . . ?
H5A O5 H5B 108.2 . . ?

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
O3 P1 O1 C1 -10.28(19) . . . . ?
O2 P1 O1 C1 -137.96(17) . . . . ?
O4 P1 O1 C1 105.84(18) . . . . ?
C1 C2 C3 C4 -1.9(3) . . . . ?
C7 C2 C3 C4 173.7(2) . . . . ?
P1 O1 C1 C6 -88.0(2) . . . . ?
P1 O1 C1 C2 95.9(2) . . . . ?
C3 C2 C1 O1 177.25(19) . . . . ?
C7 C2 C1 O1 1.6(3) . . . . ?
C3 C2 C1 C6 1.2(3) . . . . ?
C7 C2 C1 C6 -174.4(2) . . . . ?
C4 C5 C6 C1 -1.3(3) . . . . ?
C4 C5 C6 C10 -179.5(2) . . . . ?
O1 C1 C6 C5 -175.57(19) . . . . ?
C2 C1 C6 C5 0.4(3) . . . . ?
O1 C1 C6 C10 2.7(3) . . . . ?
C2 C1 C6 C10 178.6(2) . . . . ?
C11 C10 C6 C5 -18.1(3) . . . . ?
C12 C10 C6 C5 107.1(3) . . . . ?
C11 C10 C6 C1 163.8(2) . . . . ?
C12 C10 C6 C1 -71.1(3) . . . . ?
C6 C5 C4 C3 0.7(3) . . . . ?
C6 C5 C4 N1 -179.8(2) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
C2 C3 C4 N1 -178.58(19) . . . . ?
C3 C2 C7 C9 26.7(3) . . . . ?
C1 C2 C7 C9 -157.8(2) . . . . ?
C3 C2 C7 C8 -96.0(3) . . . . ?
C1 C2 C7 C8 79.5(3) . . . . ?
C13 N2 C17 C16 -0.8(4) . . . . ?
C13 N2 C17 C18 -179.5(2) . . . . ?
C24 N3 C18 C19 -1.4(4) . . . . ?
C24 N3 C18 C17 177.6(2) . . . . ?
N2 C17 C18 N3 -0.3(3) . . . . ?
C16 C17 C18 N3 -178.9(2) . . . . ?
N2 C17 C18 C19 178.7(2) . . . . ?
C16 C17 C18 C19 0.1(3) . . . . ?
N2 C17 C16 C15 1.6(4) . . . . ?
C18 C17 C16 C15 -179.7(2) . . . . ?
N2 C17 C16 C21 -177.3(2) . . . . ?
C18 C17 C16 C21 1.4(4) . . . . ?
C17 N2 C13 C14 -0.8(4) . . . . ?
C19 C20 C21 C16 1.8(4) . . . . ?
C15 C16 C21 C20 178.8(2) . . . . ?
C17 C16 C21 C20 -2.3(4) . . . . ?
C18 N3 C24 C23 1.8(4) . . . . ?
N2 C13 C14 C15 1.6(4) . . . . ?
C13 C14 C15 C16 -0.7(4) . . . . ?
C17 C16 C15 C14 -0.8(4) . . . . ?
C21 C16 C15 C14 178.1(2) . . . . ?
C19 C22 C23 C24 -2.2(4) . . . . ?
N3 C24 C23 C22 0.0(4) . . . . ?
C23 C22 C19 C18 2.5(4) . . . . ?
C23 C22 C19 C20 -176.5(2) . . . . ?
N3 C18 C19 C22 -0.7(4) . . . . ?
C17 C18 C19 C22 -179.6(2) . . . . ?
N3 C18 C19 C20 178.3(2) . . . . ?
C17 C18 C19 C20 -0.7(4) . . . . ?
C21 C20 C19 C22 178.7(3) . . . . ?
C21 C20 C19 C18 -0.3(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
O4 H4 O2 0.82 1.74 2.551(2) 167.2 2_665
N1 H1A O3 0.89 1.81 2.677(3) 164.7 2_566
N1 H1B N3 0.89 2.14 2.949(3) 150.7 2_566
N1 H1C O5 0.89 1.87 2.760(3) 174.0 .
O5 H5A N2 0.85 2.07 2.866(3) 154.9 1_556
O5 H5B O2 0.79(4) 2.04(4) 2.809(3) 167(4) 1_556

_refine_diff_density_max         0.601
_refine_diff_density_min         -1.081
_refine_diff_density_rms         0.121

####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 1511000'
_audit_update_record             
;
2016-12-19 deposited with the CCDC.
2017-01-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H20 N O6 P'
_chemical_formula_sum            'C13 H20 N O6 P'
_chemical_formula_weight         317.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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                   8.9355(3)
_cell_length_b                   9.3770(3)
_cell_length_c                   9.3907(2)
_cell_angle_alpha                93.415(2)
_cell_angle_beta                 92.982(2)
_cell_angle_gamma                103.905(3)
_cell_volume                     760.63(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5931
_cell_measurement_theta_min      2.2640
_cell_measurement_theta_max      31.2300

_exptl_crystal_description       Block
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.207
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.70711
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            5597
_diffrn_reflns_av_unetI/netI     0.0180
_diffrn_reflns_av_R_equivalents  0.0150
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.009
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             2652
_reflns_number_gt                2512
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_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)+(0.0492P)²+0.2723P] 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         2652
_refine_ls_number_parameters     210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0332
_refine_ls_R_factor_gt           0.0318
_refine_ls_wR_factor_ref         0.0882
_refine_ls_wR_factor_gt          0.0870
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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
C1 C 0.06174(15) 0.20201(14) 0.77606(14) 0.0204(3) Uani 1 1 d . . . . .
C2 C -0.08429(16) 0.19558(15) 0.82622(14) 0.0216(3) Uani 1 1 d . . . . .
C3 C -0.17134(16) 0.05795(15) 0.85618(14) 0.0225(3) Uani 1 1 d . . . . .
H3 H -0.2714 0.0478 0.8901 0.027 Uiso 1 1 calc R U . . .
C4 C -0.11125(16) -0.06420(15) 0.83632(14) 0.0226(3) Uani 1 1 d . . . . .
C5 C 0.03283(16) -0.05679(15) 0.78568(14) 0.0232(3) Uani 1 1 d . . . . .
H5 H 0.0693 -0.1435 0.7722 0.028 Uiso 1 1 calc R U . . .
C6 C 0.12385(16) 0.07902(15) 0.75461(14) 0.0218(3) Uani 1 1 d . . . . .
C7 C 0.28129(17) 0.09048(16) 0.69536(16) 0.0263(3) Uani 1 1 d . . . . .
H7 H 0.3421 0.1951 0.7129 0.032 Uiso 1 1 calc R U . . .
C8 C 0.37267(18) -0.00693(19) 0.76797(19) 0.0365(4) Uani 1 1 d . . . . .
H8A H 0.3873 0.0210 0.8709 0.055 Uiso 1 1 calc R U . . .
H8B H 0.4737 0.0062 0.7277 0.055 Uiso 1 1 calc R U . . .
H8C H 0.3156 -0.1103 0.7518 0.055 Uiso 1 1 calc R U . . .
C9 C 0.2618(2) 0.0526(2) 0.53375(18) 0.0465(5) Uani 1 1 d . . . . .
H9A H 0.2050 -0.0505 0.5138 0.070 Uiso 1 1 calc R U . . .
H9B H 0.3638 0.0674 0.4951 0.070 Uiso 1 1 calc R U . . .
H9C H 0.2042 0.1166 0.4888 0.070 Uiso 1 1 calc R U . . .
C10 C -0.14976(16) 0.33093(15) 0.84201(15) 0.0243(3) Uani 1 1 d . . . . .
H10 H -0.0614 0.4203 0.8486 0.029 Uiso 1 1 calc R U . . .
C11 C -0.25321(18) 0.33602(17) 0.70798(17) 0.0318(4) Uani 1 1 d . . . . .
H11A H -0.1964 0.3269 0.6227 0.048 Uiso 1 1 calc R U . . .
H11B H -0.2835 0.4299 0.7113 0.048 Uiso 1 1 calc R U . . .
H11C H -0.3459 0.2545 0.7042 0.048 Uiso 1 1 calc R U . . .
C12 C -0.23916(19) 0.33610(17) 0.97606(17) 0.0330(4) Uani 1 1 d . . . . .
H12A H -0.3319 0.2544 0.9679 0.049 Uiso 1 1 calc R U . . .
H12B H -0.2693 0.4298 0.9858 0.049 Uiso 1 1 calc R U . . .
H12C H -0.1735 0.3273 1.0604 0.049 Uiso 1 1 calc R U . . .
C13 C 0.44931(19) 0.5734(2) 0.6931(2) 0.0395(4) Uani 1 1 d . . . . .
N1 N -0.20397(14) -0.20777(13) 0.87266(13) 0.0274(3) Uani 1 1 d . . . . .
O1 O 0.15732(11) 0.34085(10) 0.75606(10) 0.0229(2) Uani 1 1 d . . . . .
O2 O 0.07528(12) 0.33965(11) 0.49272(11) 0.0285(3) Uani 1 1 d . . . . .
O3 O 0.33870(11) 0.47279(11) 0.59156(11) 0.0279(2) Uani 1 1 d . . . . .
O4 O 0.11383(12) 0.57167(11) 0.66268(11) 0.0263(2) Uani 1 1 d . . . . .
O5 O -0.14759(14) -0.31454(12) 0.86099(14) 0.0414(3) Uani 1 1 d . . . . .
O6 O -0.33351(13) -0.21433(12) 0.91440(14) 0.0409(3) Uani 1 1 d . . . . .
P1 P 0.16338(4) 0.43202(4) 0.61919(4) 0.02081(14) Uani 1 1 d . . . . .
H4 H 0.048(4) 0.599(3) 0.605(3) 0.099(10) Uiso 1 1 d . . . . .
H13A H 0.544(2) 0.594(2) 0.651(2) 0.045(5) Uiso 1 1 d . . . . .
H13B H 0.417(3) 0.656(3) 0.718(2) 0.063(7) Uiso 1 1 d . . . . .
H13C H 0.460(3) 0.517(3) 0.787(3) 0.078(8) Uiso 1 1 d . . . . .


_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
C1 C2 1.399(2) . ?
C1 C6 1.4036(19) . ?
C1 O1 1.4039(16) . ?
C2 C3 1.390(2) . ?
C2 C10 1.5227(18) . ?
C3 C4 1.384(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.383(2) . ?
C4 N1 1.4709(18) . ?
C5 C6 1.393(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.5219(19) . ?
C7 C9 1.529(2) . ?
C7 C8 1.530(2) . ?
C7 H7 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C12 1.530(2) . ?
C10 C11 1.532(2) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 O3 1.457(2) . ?
C13 H13A 0.94(2) . ?
C13 H13B 0.92(2) . ?
C13 H13C 1.06(3) . ?
N1 O5 1.2261(16) . ?
N1 O6 1.2300(17) . ?
O1 P1 1.5816(10) . ?
O2 P1 1.4943(11) . ?
O3 P1 1.5601(10) . ?
O4 P1 1.5204(10) . ?
O4 H4 0.87(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
C2 C1 C6 124.02(12) . . ?
C2 C1 O1 118.31(12) . . ?
C6 C1 O1 117.49(12) . . ?
C3 C2 C1 117.05(12) . . ?
C3 C2 C10 120.69(12) . . ?
C1 C2 C10 122.20(12) . . ?
C4 C3 C2 119.58(13) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C5 C4 C3 122.91(13) . . ?
C5 C4 N1 118.64(12) . . ?
C3 C4 N1 118.45(13) . . ?
C4 C5 C6 119.33(13) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 117.11(13) . . ?
C5 C6 C7 120.66(12) . . ?
C1 C6 C7 122.20(12) . . ?
C6 C7 C9 109.85(13) . . ?
C6 C7 C8 112.68(12) . . ?
C9 C7 C8 110.48(13) . . ?
C6 C7 H7 107.9 . . ?
C9 C7 H7 107.9 . . ?
C8 C7 H7 107.9 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C2 C10 C12 113.12(11) . . ?
C2 C10 C11 109.19(12) . . ?
C12 C10 C11 110.35(12) . . ?
C2 C10 H10 108.0 . . ?
C12 C10 H10 108.0 . . ?
C11 C10 H10 108.0 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 C13 H13A 106.9(12) . . ?
O3 C13 H13B 111.8(15) . . ?
H13A C13 H13B 112.8(19) . . ?
O3 C13 H13C 107.8(14) . . ?
H13A C13 H13C 109.0(18) . . ?
H13B C13 H13C 108(2) . . ?
O5 N1 O6 123.36(12) . . ?
O5 N1 C4 118.29(12) . . ?
O6 N1 C4 118.35(12) . . ?
C1 O1 P1 128.26(8) . . ?
C13 O3 P1 120.22(10) . . ?
P1 O4 H4 118(2) . . ?
O2 P1 O4 116.45(6) . . ?
O2 P1 O3 108.98(6) . . ?
O4 P1 O3 109.19(6) . . ?
O2 P1 O1 111.37(5) . . ?
O4 P1 O1 106.75(6) . . ?
O3 P1 O1 103.27(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
C6 C1 C2 C3 0.1(2) . . . . ?
O1 C1 C2 C3 -174.87(11) . . . . ?
C6 C1 C2 C10 -177.40(12) . . . . ?
O1 C1 C2 C10 7.66(19) . . . . ?
C1 C2 C3 C4 0.29(19) . . . . ?
C10 C2 C3 C4 177.80(12) . . . . ?
C2 C3 C4 C5 -0.8(2) . . . . ?
C2 C3 C4 N1 178.31(11) . . . . ?
C3 C4 C5 C6 0.9(2) . . . . ?
N1 C4 C5 C6 -178.20(12) . . . . ?
C4 C5 C6 C1 -0.50(19) . . . . ?
C4 C5 C6 C7 -178.52(12) . . . . ?
C2 C1 C6 C5 0.0(2) . . . . ?
O1 C1 C6 C5 175.01(11) . . . . ?
C2 C1 C6 C7 178.02(12) . . . . ?
O1 C1 C6 C7 -7.00(19) . . . . ?
C5 C6 C7 C9 82.44(17) . . . . ?
C1 C6 C7 C9 -95.48(16) . . . . ?
C5 C6 C7 C8 -41.20(19) . . . . ?
C1 C6 C7 C8 140.88(14) . . . . ?
C3 C2 C10 C12 41.54(18) . . . . ?
C1 C2 C10 C12 -141.08(14) . . . . ?
C3 C2 C10 C11 -81.76(16) . . . . ?
C1 C2 C10 C11 95.62(15) . . . . ?
C5 C4 N1 O5 2.34(19) . . . . ?
C3 C4 N1 O5 -176.81(13) . . . . ?
C5 C4 N1 O6 -178.29(13) . . . . ?
C3 C4 N1 O6 2.57(19) . . . . ?
C2 C1 O1 P1 -87.23(14) . . . . ?
C6 C1 O1 P1 97.50(13) . . . . ?
C13 O3 P1 O2 174.62(12) . . . . ?
C13 O3 P1 O4 46.42(13) . . . . ?
C13 O3 P1 O1 -66.88(13) . . . . ?
C1 O1 P1 O2 -12.29(13) . . . . ?
C1 O1 P1 O4 115.83(11) . . . . ?
C1 O1 P1 O3 -129.10(11) . . . . ?

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
O4 H4 O2 0.87(3) 1.63(3) 2.4979(14) 176(3) 2_566

_refine_diff_density_max         0.288
_refine_diff_density_min         -0.322
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_A
_database_code_depnum_ccdc_archive 'CCDC 1510995'
_audit_update_record             
;
2016-12-19 deposited with the CCDC.
2017-01-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H18 N O6 P, C H4 O'
_chemical_formula_sum            'C13 H22 N O7 P'
_chemical_formula_weight         335.28

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'

_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                   14.0712(3)
_cell_length_b                   7.6213(2)
_cell_length_c                   15.6474(4)
_cell_angle_alpha                90
_cell_angle_beta                 109.970(2)
_cell_angle_gamma                90
_cell_volume                     1577.14(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9514
_cell_measurement_theta_min      3.0220
_cell_measurement_theta_max      72.7700

_exptl_crystal_description       Plate
_exptl_crystal_colour            Colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_F_000             712
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    1.868
_shelx_estimated_absorpt_T_min   0.706
_shelx_estimated_absorpt_T_max   0.835
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.38745
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12211
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_av_R_equivalents  0.0372
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         3.342
_diffrn_reflns_theta_max         67.498
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measured_fraction_theta_full 0.948
_diffrn_reflns_Laue_measured_fraction_max 0.952
_diffrn_reflns_Laue_measured_fraction_full 0.948
_diffrn_reflns_point_group_measured_fraction_max 0.952
_diffrn_reflns_point_group_measured_fraction_full 0.948
_reflns_number_total             2704
_reflns_number_gt                2527
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'

_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)+(0.0644P)²+0.5920P]
 where P=(Fo²+2Fc²)/3
;
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2704
_refine_ls_number_parameters     207
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0400
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.1006
_refine_ls_wR_factor_gt          0.0985
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_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
C1 C 0.22737(10) 0.4814(2) 0.57385(9) 0.0161(3) Uani 1 1 d . . . . .
C2 C 0.19094(11) 0.6343(2) 0.60115(10) 0.0170(3) Uani 1 1 d . . . . .
C3 C 0.11013(10) 0.7194(2) 0.53651(9) 0.0176(3) Uani 1 1 d . . . . .
H3 H 0.0823 0.8231 0.5521 0.021 Uiso 1 1 calc R U . . .
C4 C 0.07123(10) 0.6513(2) 0.44977(10) 0.0170(3) Uani 1 1 d . . . . .
C5 C 0.10887(10) 0.5019(2) 0.42288(9) 0.0176(3) Uani 1 1 d . . . . .
H5 H 0.0806 0.4605 0.3621 0.021 Uiso 1 1 calc R U . . .
C6 C 0.18880(11) 0.4124(2) 0.48574(10) 0.0172(3) Uani 1 1 d . . . . .
C7 C 0.23577(11) 0.7124(2) 0.69582(10) 0.0221(4) Uani 1 1 d . . . . .
H7 H 0.2880 0.6292 0.7341 0.027 Uiso 1 1 calc R U . . .
C8 C 0.28758(12) 0.8876(2) 0.69280(11) 0.0258(4) Uani 1 1 d . . . . .
H8A H 0.2368 0.9738 0.6594 0.039 Uiso 1 1 calc R U . . .
H8B H 0.3371 0.8717 0.6621 0.039 Uiso 1 1 calc R U . . .
H8C H 0.3220 0.9295 0.7549 0.039 Uiso 1 1 calc R U . . .
C9 C 0.15489(12) 0.7356(2) 0.74008(10) 0.0262(4) Uani 1 1 d . . . . .
H9A H 0.1214 0.6230 0.7404 0.039 Uiso 1 1 calc R U . . .
H9B H 0.1048 0.8217 0.7055 0.039 Uiso 1 1 calc R U . . .
H9C H 0.1867 0.7771 0.8027 0.039 Uiso 1 1 calc R U . . .
C10 C 0.23000(11) 0.2481(2) 0.45619(10) 0.0189(3) Uani 1 1 d . . . . .
H10 H 0.2835 0.1977 0.5106 0.023 Uiso 1 1 calc R U . . .
C11 C 0.27869(12) 0.2942(2) 0.38540(11) 0.0256(4) Uani 1 1 d . . . . .
H11A H 0.2268 0.3387 0.3303 0.038 Uiso 1 1 calc R U . . .
H11B H 0.3099 0.1890 0.3704 0.038 Uiso 1 1 calc R U . . .
H11C H 0.3305 0.3843 0.4100 0.038 Uiso 1 1 calc R U . . .
C12 C 0.14705(12) 0.1106(2) 0.41969(11) 0.0217(4) Uani 1 1 d . . . . .
H12A H 0.0945 0.1566 0.3655 0.033 Uiso 1 1 calc R U . . .
H12B H 0.1174 0.0832 0.4664 0.033 Uiso 1 1 calc R U . . .
H12C H 0.1760 0.0039 0.4037 0.033 Uiso 1 1 calc R U . . .
C13 C 0.62441(14) 0.1669(3) 0.52613(13) 0.0364(5) Uani 1 1 d . . . . .
H13A H 0.5949 0.0799 0.4783 0.055 Uiso 1 1 calc R U . . .
H13B H 0.6397 0.1114 0.5858 0.055 Uiso 1 1 calc R U . . .
H13C H 0.6868 0.2135 0.5203 0.055 Uiso 1 1 calc R U . . .
N1 N -0.01411(9) 0.74288(17) 0.38255(8) 0.0184(3) Uani 1 1 d . . . . .
O1 O 0.30077(7) 0.38377(14) 0.64030(7) 0.0172(3) Uani 1 1 d . . . . .
O2 O 0.45539(8) 0.25101(14) 0.62145(7) 0.0211(3) Uani 1 1 d . . . . .
H2 H 0.4839 0.2938 0.5870 0.032 Uiso 1 1 calc R U . . .
O3 O 0.45313(8) 0.35453(15) 0.77139(7) 0.0207(3) Uani 1 1 d . . . . .
H3A H 0.4833 0.2576 0.7805 0.031 Uiso 1 1 calc R U . . .
O4 O 0.45106(8) 0.57763(14) 0.65004(7) 0.0191(3) Uani 1 1 d . . . . .
O5 O -0.05111(8) 0.86906(15) 0.40774(7) 0.0258(3) Uani 1 1 d . . . . .
O6 O -0.04368(9) 0.68889(18) 0.30413(7) 0.0330(3) Uani 1 1 d . . . . .
O7 O 0.55467(8) 0.30580(16) 0.51743(7) 0.0270(3) Uani 1 1 d . . . . .
H7A H 0.5393 0.3501 0.4653 0.040 Uiso 1 1 calc R U . . .
P1 P 0.41990(3) 0.40030(5) 0.66964(2) 0.01582(15) Uani 1 1 d . . . . .


_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
C1 C2 1.398(2) . ?
C1 C6 1.400(2) . ?
C1 O1 1.4027(17) . ?
C2 C3 1.397(2) . ?
C2 C7 1.519(2) . ?
C3 C4 1.380(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(2) . ?
C4 N1 1.4742(18) . ?
C5 C6 1.394(2) . ?
C5 H5 0.9500 . ?
C6 C10 1.517(2) . ?
C7 C8 1.530(2) . ?
C7 C9 1.531(2) . ?
C7 H7 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C12 1.527(2) . ?
C10 C11 1.529(2) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 O7 1.418(2) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
N1 O5 1.2212(17) . ?
N1 O6 1.2245(17) . ?
O1 P1 1.5846(10) . ?
O2 P1 1.5393(11) . ?
O2 H2 0.8400 . ?
O3 P1 1.5384(10) . ?
O3 H3A 0.8400 . ?
O4 P1 1.4848(12) . ?
O7 H7A 0.8400 . ?

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
C2 C1 C6 123.70(13) . . ?
C2 C1 O1 118.02(12) . . ?
C6 C1 O1 118.06(13) . . ?
C3 C2 C1 117.31(13) . . ?
C3 C2 C7 119.24(14) . . ?
C1 C2 C7 123.45(13) . . ?
C4 C3 C2 119.26(14) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 123.06(13) . . ?
C3 C4 N1 118.44(13) . . ?
C5 C4 N1 118.49(12) . . ?
C4 C5 C6 119.32(13) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 117.33(14) . . ?
C5 C6 C10 119.29(13) . . ?
C1 C6 C10 123.38(13) . . ?
C2 C7 C8 110.82(13) . . ?
C2 C7 C9 111.17(12) . . ?
C8 C7 C9 110.38(13) . . ?
C2 C7 H7 108.1 . . ?
C8 C7 H7 108.1 . . ?
C9 C7 H7 108.1 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 C12 110.94(12) . . ?
C6 C10 C11 110.10(13) . . ?
C12 C10 C11 111.17(13) . . ?
C6 C10 H10 108.2 . . ?
C12 C10 H10 108.2 . . ?
C11 C10 H10 108.2 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O7 C13 H13A 109.5 . . ?
O7 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O7 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O5 N1 O6 123.48(12) . . ?
O5 N1 C4 118.42(12) . . ?
O6 N1 C4 118.10(12) . . ?
C1 O1 P1 127.66(9) . . ?
P1 O2 H2 109.5 . . ?
P1 O3 H3A 109.5 . . ?
C13 O7 H7A 109.5 . . ?
O4 P1 O3 114.41(6) . . ?
O4 P1 O2 113.80(6) . . ?
O3 P1 O2 107.73(6) . . ?
O4 P1 O1 111.73(6) . . ?
O3 P1 O1 101.50(6) . . ?
O2 P1 O1 106.70(6) . . ?

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
C6 C1 C2 C3 1.3(2) . . . . ?
O1 C1 C2 C3 -173.08(13) . . . . ?
C6 C1 C2 C7 -177.54(14) . . . . ?
O1 C1 C2 C7 8.0(2) . . . . ?
C1 C2 C3 C4 -0.7(2) . . . . ?
C7 C2 C3 C4 178.19(13) . . . . ?
C2 C3 C4 C5 -0.4(2) . . . . ?
C2 C3 C4 N1 179.94(13) . . . . ?
C3 C4 C5 C6 1.1(2) . . . . ?
N1 C4 C5 C6 -179.29(13) . . . . ?
C4 C5 C6 C1 -0.5(2) . . . . ?
C4 C5 C6 C10 179.91(13) . . . . ?
C2 C1 C6 C5 -0.7(2) . . . . ?
O1 C1 C6 C5 173.70(12) . . . . ?
C2 C1 C6 C10 178.87(13) . . . . ?
O1 C1 C6 C10 -6.7(2) . . . . ?
C3 C2 C7 C8 -66.70(17) . . . . ?
C1 C2 C7 C8 112.17(16) . . . . ?
C3 C2 C7 C9 56.46(19) . . . . ?
C1 C2 C7 C9 -124.68(15) . . . . ?
C5 C6 C10 C12 -57.91(17) . . . . ?
C1 C6 C10 C12 122.51(15) . . . . ?
C5 C6 C10 C11 65.58(17) . . . . ?
C1 C6 C10 C11 -114.00(15) . . . . ?
C3 C4 N1 O5 -4.5(2) . . . . ?
C5 C4 N1 O5 175.85(13) . . . . ?
C3 C4 N1 O6 175.01(14) . . . . ?
C5 C4 N1 O6 -4.7(2) . . . . ?
C2 C1 O1 P1 -91.67(15) . . . . ?
C6 C1 O1 P1 93.59(15) . . . . ?
C1 O1 P1 O4 24.86(13) . . . . ?
C1 O1 P1 O3 147.21(12) . . . . ?
C1 O1 P1 O2 -100.12(12) . . . . ?

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
C3 H3 O5 0.95 2.51 3.4325(19) 165.0 3_576
O2 H2 O7 0.84 1.71 2.5155(15) 159.8 .
O3 H3A O4 0.84 1.80 2.5788(15) 154.2 2_646
O7 H7A O4 0.84 1.94 2.7420(15) 160.6 3_666
C3 H3 O5 0.95 2.51 3.4325(19) 165.0 3_576
O2 H2 O7 0.84 1.71 2.5155(15) 159.8 .
O3 H3A O4 0.84 1.80 2.5788(15) 154.2 2_646
O7 H7A O4 0.84 1.94 2.7420(15) 160.6 3_666

_refine_diff_density_max         0.388
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.062

_shelxl_version_number           2014/7

####################################################################### 
# 
# 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_4
_database_code_depnum_ccdc_archive 'CCDC 1510999'
_audit_update_record             
;
2016-12-19 deposited with the CCDC.
2017-01-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H22 N O5 P'
_chemical_formula_sum            'C14 H22 N O5 P'
_chemical_formula_weight         315.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      tetragonal
_space_group_IT_number           96
_space_group_name_H-M_alt        'P 43 21 2'
_space_group_name_Hall           'P 4nw 2abw'

_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'
'-y+1/2, x+1/2, z+3/4'
'-x, -y, z+1/2'
'y+1/2, -x+1/2, z+1/4'
'x+1/2, -y+1/2, -z+1/4'
'-x+1/2, y+1/2, -z+3/4'
'y, x, -z'
'-y, -x, -z+1/2'

_cell_length_a                   10.145(3)
_cell_length_b                   10.145(3)
_cell_length_c                   31.351(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3227(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    14061
_cell_measurement_theta_min      2.3710
_cell_measurement_theta_max      30.8370

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_F_000             1344
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.190
_shelx_estimated_absorpt_T_min   0.963
_shelx_estimated_absorpt_T_max   0.963
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.74398
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            6139
_diffrn_reflns_av_unetI/netI     0.0660
_diffrn_reflns_av_R_equivalents  0.0439
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.798
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        24.997
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2813
_reflns_number_gt                2533
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.636
_reflns_Friedel_fraction_max     0.991
_reflns_Friedel_fraction_full    0.991

_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_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)+(0.0321P)²+1.8875P] 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_abs_structure_details 
;
 Flack x determined using 703 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(10)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2813
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0548
_refine_ls_wR_factor_ref         0.1077
_refine_ls_wR_factor_gt          0.1045
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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
C1 C 0.3371(4) 0.7953(4) 0.58067(13) 0.0207(10) Uani 1 1 d . . . . .
C2 C 0.3034(4) 0.8946(4) 0.55194(13) 0.0205(10) Uani 1 1 d . . . . .
C3 C 0.2320(5) 1.0014(4) 0.56686(13) 0.0246(11) Uani 1 1 d . . . . .
H3 H 0.2076 1.0701 0.5478 0.030 Uiso 1 1 calc R U . . .
C4 C 0.1961(5) 1.0085(4) 0.60932(14) 0.0248(10) Uani 1 1 d . . . . .
C5 C 0.2322(5) 0.9102(4) 0.63724(13) 0.0247(11) Uani 1 1 d . . . . .
H5 H 0.2070 0.9169 0.6663 0.030 Uiso 1 1 calc R U . . .
C6 C 0.3043(4) 0.8015(4) 0.62394(13) 0.0206(10) Uani 1 1 d . . . . .
C7 C 0.3427(5) 0.8892(4) 0.50492(13) 0.0272(11) Uani 1 1 d . . . . .
H7 H 0.4006 0.8105 0.5008 0.033 Uiso 1 1 calc R U . . .
C8 C 0.2240(5) 0.8741(5) 0.47605(13) 0.0386(13) Uani 1 1 d . . . . .
H8A H 0.1737 0.7959 0.4846 0.058 Uiso 1 1 calc R U . . .
H8B H 0.2536 0.8640 0.4465 0.058 Uiso 1 1 calc R U . . .
H8C H 0.1680 0.9524 0.4784 0.058 Uiso 1 1 calc R U . . .
C9 C 0.4229(5) 1.0122(5) 0.49344(16) 0.0429(15) Uani 1 1 d . . . . .
H9A H 0.3679 1.0908 0.4971 0.064 Uiso 1 1 calc R U . . .
H9B H 0.4521 1.0062 0.4637 0.064 Uiso 1 1 calc R U . . .
H9C H 0.4999 1.0183 0.5122 0.064 Uiso 1 1 calc R U . . .
C10 C 0.3468(5) 0.6973(5) 0.65624(13) 0.0281(12) Uani 1 1 d . . . . .
H10 H 0.3853 0.6217 0.6400 0.034 Uiso 1 1 calc R U . . .
C11 C 0.2311(6) 0.6457(5) 0.68149(16) 0.0437(14) Uani 1 1 d . . . . .
H11A H 0.1987 0.7149 0.7006 0.065 Uiso 1 1 calc R U . . .
H11B H 0.2589 0.5693 0.6984 0.065 Uiso 1 1 calc R U . . .
H11C H 0.1606 0.6194 0.6619 0.065 Uiso 1 1 calc R U . . .
C12 C 0.4535(6) 0.7508(6) 0.68573(16) 0.0481(15) Uani 1 1 d . . . . .
H12A H 0.5252 0.7883 0.6686 0.072 Uiso 1 1 calc R U . . .
H12B H 0.4880 0.6791 0.7035 0.072 Uiso 1 1 calc R U . . .
H12C H 0.4160 0.8195 0.7041 0.072 Uiso 1 1 calc R U . . .
C13 C 0.1279(5) 1.2414(5) 0.61676(13) 0.0267(10) Uani 1 1 d . . . . .
N1 N 0.1190(4) 1.1141(3) 0.62582(11) 0.0269(9) Uani 1 1 d . . . . .
H1 H 0.0577 1.0921 0.6444 0.032 Uiso 1 1 calc R U . . .
O1 O 0.4150(3) 0.6897(3) 0.56646(9) 0.0207(7) Uani 1 1 d . . . . .
O2 O 0.2438(4) 0.5192(3) 0.57919(10) 0.0293(8) Uani 1 1 d . . . . .
O3 O 0.4746(3) 0.4583(3) 0.55272(9) 0.0270(8) Uani 1 1 d . . . . .
O4 O 0.3090(3) 0.5699(3) 0.50489(9) 0.0256(8) Uani 1 1 d . . . . .
H4 H 0.3598 0.5320 0.4877 0.038 Uiso 1 1 calc R U . . .
O5 O 0.2078(4) 1.2825(3) 0.58918(11) 0.0392(9) Uani 1 1 d . . . . .
P1 P 0.36140(12) 0.55197(12) 0.55068(4) 0.0215(3) Uani 1 1 d . . . . .
C14 C 0.0413(5) 1.3345(5) 0.64095(15) 0.0333(12) Uani 1 1 d . . . . .
H14A H -0.0325 1.2858 0.6535 0.050 Uiso 1 1 calc R U . . .
H14B H 0.0073 1.4021 0.6215 0.050 Uiso 1 1 calc R U . . .
H14C H 0.0924 1.3767 0.6637 0.050 Uiso 1 1 calc R U . . .
H2 H 0.224(7) 0.431(7) 0.585(2) 0.09(2) Uiso 1 1 d . . . . .


_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
C1 C2 1.395(6) . ?
C1 C6 1.398(6) . ?
C1 O1 1.403(5) . ?
C2 C3 1.384(6) . ?
C2 C7 1.528(6) . ?
C3 C4 1.382(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.376(6) . ?
C4 N1 1.424(5) . ?
C5 C6 1.388(6) . ?
C5 H5 0.9500 . ?
C6 C10 1.526(6) . ?
C7 C8 1.514(6) . ?
C7 C9 1.532(7) . ?
C7 H7 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.510(7) . ?
C10 C12 1.524(7) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 O5 1.257(5) . ?
C13 N1 1.325(6) . ?
C13 C14 1.497(6) . ?
N1 H1 0.8800 . ?
O1 P1 1.579(3) . ?
O2 P1 1.527(3) . ?
O2 H2 0.93(7) . ?
O3 P1 1.492(3) . ?
O4 P1 1.542(3) . ?
O4 H4 0.8400 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 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
C2 C1 C6 122.4(4) . . ?
C2 C1 O1 119.0(4) . . ?
C6 C1 O1 118.5(4) . . ?
C3 C2 C1 118.4(4) . . ?
C3 C2 C7 119.4(4) . . ?
C1 C2 C7 122.2(4) . . ?
C4 C3 C2 120.3(4) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 120.3(4) . . ?
C5 C4 N1 117.4(4) . . ?
C3 C4 N1 122.3(4) . . ?
C4 C5 C6 121.7(4) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C1 116.9(4) . . ?
C5 C6 C10 120.0(4) . . ?
C1 C6 C10 123.0(4) . . ?
C8 C7 C2 111.9(4) . . ?
C8 C7 C9 111.4(4) . . ?
C2 C7 C9 109.6(4) . . ?
C8 C7 H7 107.9 . . ?
C2 C7 H7 107.9 . . ?
C9 C7 H7 107.9 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C12 111.0(4) . . ?
C11 C10 C6 111.6(4) . . ?
C12 C10 C6 110.9(4) . . ?
C11 C10 H10 107.7 . . ?
C12 C10 H10 107.7 . . ?
C6 C10 H10 107.7 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O5 C13 N1 121.0(4) . . ?
O5 C13 C14 121.2(4) . . ?
N1 C13 C14 117.8(4) . . ?
C13 N1 C4 128.2(4) . . ?
C13 N1 H1 115.9 . . ?
C4 N1 H1 115.9 . . ?
C1 O1 P1 125.5(3) . . ?
P1 O2 H2 119(4) . . ?
P1 O4 H4 109.5 . . ?
O3 P1 O2 116.0(2) . . ?
O3 P1 O4 112.36(18) . . ?
O2 P1 O4 107.55(19) . . ?
O3 P1 O1 106.55(18) . . ?
O2 P1 O1 106.16(17) . . ?
O4 P1 O1 107.82(17) . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
C6 C1 C2 C3 -1.6(7) . . . . ?
O1 C1 C2 C3 -176.9(4) . . . . ?
C6 C1 C2 C7 178.3(4) . . . . ?
O1 C1 C2 C7 3.0(6) . . . . ?
C1 C2 C3 C4 0.3(7) . . . . ?
C7 C2 C3 C4 -179.6(4) . . . . ?
C2 C3 C4 C5 0.7(7) . . . . ?
C2 C3 C4 N1 -177.9(4) . . . . ?
C3 C4 C5 C6 -0.3(7) . . . . ?
N1 C4 C5 C6 178.3(4) . . . . ?
C4 C5 C6 C1 -1.0(7) . . . . ?
C4 C5 C6 C10 177.7(4) . . . . ?
C2 C1 C6 C5 2.0(7) . . . . ?
O1 C1 C6 C5 177.2(4) . . . . ?
C2 C1 C6 C10 -176.6(4) . . . . ?
O1 C1 C6 C10 -1.4(7) . . . . ?
C3 C2 C7 C8 -66.9(6) . . . . ?
C1 C2 C7 C8 113.2(5) . . . . ?
C3 C2 C7 C9 57.2(6) . . . . ?
C1 C2 C7 C9 -122.7(5) . . . . ?
C5 C6 C10 C11 53.7(6) . . . . ?
C1 C6 C10 C11 -127.7(5) . . . . ?
C5 C6 C10 C12 -70.6(6) . . . . ?
C1 C6 C10 C12 108.0(5) . . . . ?
O5 C13 N1 C4 3.4(8) . . . . ?
C14 C13 N1 C4 -175.6(4) . . . . ?
C5 C4 N1 C13 140.6(5) . . . . ?
C3 C4 N1 C13 -40.8(7) . . . . ?
C2 C1 O1 P1 -95.7(4) . . . . ?
C6 C1 O1 P1 88.8(5) . . . . ?
C1 O1 P1 O3 -161.6(3) . . . . ?
C1 O1 P1 O2 -37.4(4) . . . . ?
C1 O1 P1 O4 77.6(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
N1 H1 O3 0.88 1.93 2.776(5) 160.7 5_466
O4 H4 O3 0.84 1.71 2.548(4) 171.1 7_556
O2 H2 O5 0.93(7) 1.52(7) 2.449(5) 171(7) 1_545
N1 H1 O3 0.88 1.93 2.776(5) 160.7 5_466
O4 H4 O3 0.84 1.71 2.548(4) 171.1 7_556
O2 H2 O5 0.93(7) 1.52(7) 2.449(5) 171(7) 1_545

_refine_diff_density_max         0.299
_refine_diff_density_min         -0.261
_refine_diff_density_rms         0.048

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1510997'
_audit_update_record             
;
2016-12-19 deposited with the CCDC.
2017-01-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
'2(C12 H20 N O4 P), C12 H21 N O4 P, C F3 O3 S, H2 O'
_chemical_formula_sum            'C37 H63 F3 N3 O16 P3 S'
_chemical_formula_weight         987.87

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'
F F 0.0171 0.0103 '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                   13.2233(4)
_cell_length_b                   13.8858(6)
_cell_length_c                   14.5180(9)
_cell_angle_alpha                84.034(4)
_cell_angle_beta                 80.465(4)
_cell_angle_gamma                80.694(3)
_cell_volume                     2586.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9660
_cell_measurement_theta_min      1.8580
_cell_measurement_theta_max      30.3720

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.269
_exptl_crystal_F_000             1044
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.020
_exptl_absorpt_coefficient_mu    0.229
_shelx_estimated_absorpt_T_min   0.949
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.72395
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            19791
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.326
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             9089
_reflns_number_gt                7210
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_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)+(0.0725P)²+2.1471P] 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         9089
_refine_ls_number_parameters     621
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0719
_refine_ls_R_factor_gt           0.0554
_refine_ls_wR_factor_ref         0.1515
_refine_ls_wR_factor_gt          0.1399
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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
C1 C 0.2992(2) 0.94502(19) 0.9845(2) 0.0343(6) Uani 1 1 d . . . . .
C2 C 0.2497(2) 0.9911(2) 1.0641(2) 0.0344(6) Uani 1 1 d . . . . .
C3 C 0.2740(2) 1.0832(2) 1.0742(2) 0.0364(7) Uani 1 1 d . . . . .
H3 H 0.2414 1.1178 1.1268 0.044 Uiso 1 1 calc R U . . .
C4 C 0.3451(2) 1.12378(19) 1.0079(2) 0.0349(7) Uani 1 1 d . . . . .
C5 C 0.3937(2) 1.0775(2) 0.9295(2) 0.0365(7) Uani 1 1 d . . . . .
H5 H 0.4426 1.1077 0.8851 0.044 Uiso 1 1 calc R U . . .
C6 C 0.3705(2) 0.9860(2) 0.9157(2) 0.0349(6) Uani 1 1 d . . . . .
C7 C 0.4193(3) 0.9328(2) 0.8289(2) 0.0430(8) Uani 1 1 d . . . . .
H7 H 0.4407 0.8627 0.8500 0.052 Uiso 1 1 calc R U . . .
C8 C 0.5159(3) 0.9724(2) 0.7765(2) 0.0490(8) Uani 1 1 d . . . . .
H8A H 0.5660 0.9707 0.8197 0.073 Uiso 1 1 calc R U . . .
H8B H 0.4967 1.0400 0.7515 0.073 Uiso 1 1 calc R U . . .
H8C H 0.5471 0.9318 0.7249 0.073 Uiso 1 1 calc R U . . .
C9 C 0.3385(3) 0.9354(3) 0.7640(2) 0.0618(10) Uani 1 1 d . . . . .
H9A H 0.3169 1.0033 0.7410 0.093 Uiso 1 1 calc R U . . .
H9B H 0.2782 0.9080 0.7987 0.093 Uiso 1 1 calc R U . . .
H9C H 0.3688 0.8967 0.7108 0.093 Uiso 1 1 calc R U . . .
C10 C 0.1706(2) 0.9437(2) 1.1360(2) 0.0430(8) Uani 1 1 d . . . . .
H10A H 0.1930 0.8713 1.1377 0.052 Uiso 1 1 calc R U . . .
C11 C 0.1644(3) 0.9731(3) 1.2343(3) 0.0628(10) Uani 1 1 d . . . . .
H11A H 0.1329 1.0418 1.2375 0.094 Uiso 1 1 calc R U . . .
H11B H 0.2344 0.9648 1.2509 0.094 Uiso 1 1 calc R U . . .
H11C H 0.1221 0.9317 1.2782 0.094 Uiso 1 1 calc R U . . .
C12 C 0.0655(3) 0.9642(3) 1.1034(3) 0.0703(11) Uani 1 1 d . . . . .
H12A H 0.0710 0.9394 1.0417 0.105 Uiso 1 1 calc R U . . .
H12B H 0.0419 1.0349 1.0991 0.105 Uiso 1 1 calc R U . . .
H12C H 0.0155 0.9315 1.1483 0.105 Uiso 1 1 calc R U . . .
C13 C 0.8764(2) 0.5232(2) 0.17774(19) 0.0319(6) Uani 1 1 d . . . . .
C14 C 0.9207(2) 0.6038(2) 0.1925(2) 0.0363(7) Uani 1 1 d . . . . .
C15 C 1.0277(2) 0.5975(2) 0.1709(2) 0.0376(7) Uani 1 1 d . . . . .
H15 H 1.0609 0.6506 0.1804 0.045 Uiso 1 1 calc R U . . .
C16 C 1.0857(2) 0.5141(2) 0.1356(2) 0.0329(6) Uani 1 1 d . . . . .
C17 C 1.0413(2) 0.4346(2) 0.1222(2) 0.0328(6) Uani 1 1 d . . . . .
H17 H 1.0835 0.3781 0.0979 0.039 Uiso 1 1 calc R U . . .
C18 C 0.9346(2) 0.4371(2) 0.1442(2) 0.0331(6) Uani 1 1 d . . . . .
C19 C 0.8831(2) 0.3487(2) 0.1354(2) 0.0408(7) Uani 1 1 d . . . . .
H19 H 0.8192 0.3733 0.1064 0.049 Uiso 1 1 calc R U . . .
C20 C 0.8488(3) 0.2990(2) 0.2319(3) 0.0613(10) Uani 1 1 d . . . . .
H20A H 0.8046 0.3472 0.2714 0.092 Uiso 1 1 calc R U . . .
H20B H 0.9099 0.2714 0.2611 0.092 Uiso 1 1 calc R U . . .
H20C H 0.8098 0.2465 0.2251 0.092 Uiso 1 1 calc R U . . .
C21 C 0.9505(3) 0.2739(2) 0.0727(3) 0.0488(8) Uani 1 1 d . . . . .
H21A H 1.0107 0.2438 0.1022 0.073 Uiso 1 1 calc R U . . .
H21B H 0.9740 0.3066 0.0117 0.073 Uiso 1 1 calc R U . . .
H21C H 0.9100 0.2232 0.0642 0.073 Uiso 1 1 calc R U . . .
C22 C 0.8559(3) 0.6970(2) 0.2296(2) 0.0475(8) Uani 1 1 d . . . . .
H22 H 0.7851 0.6815 0.2559 0.057 Uiso 1 1 calc R U . . .
C23 C 0.9000(3) 0.7339(3) 0.3076(3) 0.0628(10) Uani 1 1 d . . . . .
H23A H 0.9659 0.7570 0.2819 0.094 Uiso 1 1 calc R U . . .
H23B H 0.9115 0.6805 0.3562 0.094 Uiso 1 1 calc R U . . .
H23C H 0.8509 0.7879 0.3349 0.094 Uiso 1 1 calc R U . . .
C24 C 0.8448(3) 0.7760(2) 0.1485(3) 0.0629(10) Uani 1 1 d . . . . .
H24A H 0.8194 0.7495 0.0981 0.094 Uiso 1 1 calc R U . . .
H24B H 0.9124 0.7967 0.1248 0.094 Uiso 1 1 calc R U . . .
H24C H 0.7954 0.8324 0.1708 0.094 Uiso 1 1 calc R U . . .
C25 C 0.3563(2) 0.6884(2) 0.4603(2) 0.0367(7) Uani 1 1 d . . . . .
C26 C 0.3244(2) 0.6046(2) 0.5120(2) 0.0396(7) Uani 1 1 d . . . . .
C27 C 0.3711(2) 0.5717(2) 0.5912(2) 0.0405(7) Uani 1 1 d . . . . .
H27 H 0.3533 0.5144 0.6280 0.049 Uiso 1 1 calc R U . . .
C28 C 0.4424(2) 0.6216(2) 0.6165(2) 0.0363(7) Uani 1 1 d . . . . .
C29 C 0.4706(3) 0.7046(2) 0.5653(2) 0.0459(8) Uani 1 1 d . . . . .
H29 H 0.5194 0.7382 0.5849 0.055 Uiso 1 1 calc R U . . .
C30 C 0.4278(3) 0.7395(2) 0.4849(2) 0.0435(8) Uani 1 1 d . . . . .
C31 C 0.4556(4) 0.8327(3) 0.4289(3) 0.0689(13) Uani 1 1 d . . . . .
C32 C 0.3596(6) 0.9191(4) 0.4627(4) 0.079(2) Uani 0.693(7) 1 d . . P A 1
H32A H 0.2937 0.8993 0.4555 0.119 Uiso 0.693(7) 1 calc R U P A 1
H32B H 0.3689 0.9802 0.4242 0.119 Uiso 0.693(7) 1 calc R U P A 1
H32C H 0.3593 0.9291 0.5286 0.119 Uiso 0.693(7) 1 calc R U P A 1
C33 C 0.5525(7) 0.8611(6) 0.4441(5) 0.081(3) Uani 0.667(12) 1 d . . P A 1
H33A H 0.5461 0.8782 0.5088 0.121 Uiso 0.667(12) 1 calc R U P A 1
H33B H 0.5679 0.9177 0.4009 0.121 Uiso 0.667(12) 1 calc R U P A 1
H33C H 0.6088 0.8064 0.4327 0.121 Uiso 0.667(12) 1 calc R U P A 1
C34 C 0.2402(3) 0.5558(3) 0.4840(2) 0.0576(10) Uani 1 1 d . . . . .
H34 H 0.2566 0.5506 0.4147 0.069 Uiso 1 1 calc R U . . .
C35 C 0.1345(3) 0.6192(4) 0.5033(4) 0.0967(17) Uani 1 1 d . . . . .
H35A H 0.1142 0.6230 0.5710 0.145 Uiso 1 1 calc R U . . .
H35B H 0.0829 0.5902 0.4783 0.145 Uiso 1 1 calc R U . . .
H35C H 0.1386 0.6852 0.4729 0.145 Uiso 1 1 calc R U . . .
C36 C 0.2373(4) 0.4530(3) 0.5300(3) 0.0921(17) Uani 1 1 d . . . . .
H36A H 0.3068 0.4149 0.5194 0.138 Uiso 1 1 calc R U . . .
H36B H 0.1891 0.4215 0.5028 0.138 Uiso 1 1 calc R U . . .
H36C H 0.2140 0.4559 0.5974 0.138 Uiso 1 1 calc R U . . .
C37 C 0.7914(4) 0.7579(3) 0.6376(3) 0.0638(10) Uani 1 1 d . . . . .
F1 F 0.8884(2) 0.7210(3) 0.6290(3) 0.1263(12) Uani 1 1 d . . . . .
F2 F 0.7609(3) 0.7530(2) 0.55632(17) 0.1112(11) Uani 1 1 d . . . . .
F3 F 0.7805(2) 0.85216(18) 0.65077(17) 0.0903(8) Uani 1 1 d . . . . .
N1 N 0.3714(2) 1.22037(19) 1.0214(2) 0.0380(6) Uani 1 1 d . . . . .
N2 N 1.19899(17) 0.50822(17) 0.11282(17) 0.0345(5) Uani 1 1 d . . . . .
H2A H 1.2286 0.4815 0.1637 0.041 Uiso 1 1 calc R U . . .
H2B H 1.2158 0.5694 0.0966 0.041 Uiso 1 1 calc R U . . .
H2C H 1.2227 0.4702 0.0641 0.041 Uiso 1 1 calc R U . . .
N3 N 0.4903(2) 0.58657(18) 0.70065(17) 0.0404(6) Uani 1 1 d . . . . .
H3A H 0.5325 0.5288 0.6908 0.048 Uiso 1 1 calc R U . . .
H3B H 0.4398 0.5776 0.7502 0.048 Uiso 1 1 calc R U . . .
H3C H 0.5281 0.6316 0.7130 0.048 Uiso 1 1 calc R U . . .
O1 O 0.27228(15) 0.85376(13) 0.97043(14) 0.0366(5) Uani 1 1 d . . . . .
O2 O 0.36978(18) 0.70219(15) 0.91081(14) 0.0454(5) Uani 1 1 d . . . . .
H2 H 0.3558 0.6448 0.9169 0.068 Uiso 1 1 calc R U . . .
O3 O 0.25609(15) 0.69515(13) 1.06891(13) 0.0352(5) Uani 1 1 d . . . . .
O4 O 0.42258(15) 0.76886(13) 1.04804(14) 0.0354(5) Uani 1 1 d . . . . .
O5 O 0.76854(14) 0.52608(14) 0.20182(13) 0.0354(5) Uani 1 1 d . . . . .
O6 O 0.73680(15) 0.59986(14) 0.03998(14) 0.0380(5) Uani 1 1 d . . . . .
O7 O 0.62659(15) 0.47568(13) 0.13260(14) 0.0362(5) Uani 1 1 d . . . . .
O8 O 0.61302(16) 0.64688(15) 0.18035(16) 0.0453(5) Uani 1 1 d . . . . .
H8 H 0.5633 0.6256 0.2160 0.068 Uiso 1 1 calc R U . . .
O9 O 0.30867(16) 0.72488(15) 0.38136(14) 0.0402(5) Uani 1 1 d . . . . .
O10 O 0.38739(17) 0.78662(14) 0.22408(14) 0.0417(5) Uani 1 1 d . . . . .
H10 H 0.4001 0.7782 0.1666 0.063 Uiso 1 1 calc R U . . .
O11 O 0.43695(16) 0.60969(15) 0.28035(14) 0.0423(5) Uani 1 1 d . . . . .
O12 O 0.25437(17) 0.67186(17) 0.24470(15) 0.0473(6) Uani 1 1 d . . . . .
H12 H 0.2630 0.6780 0.1859 0.071 Uiso 1 1 calc R U . . .
O13 O 0.4244(4) 0.4794(7) 0.0709(5) 0.187(2) Uani 1 1 d G . . . .
H13A H 0.3827 0.5050 0.1178 0.281 Uiso 1 1 d G U . . .
H13B H 0.4881 0.4738 0.0814 0.281 Uiso 1 1 d G U . . .
O14 O 0.7369(2) 0.59178(16) 0.71314(16) 0.0558(6) Uani 1 1 d . . . . .
O15 O 0.6102(2) 0.73687(18) 0.7258(2) 0.0697(8) Uani 1 1 d . . . . .
O16 O 0.7513(2) 0.71504(17) 0.81356(16) 0.0568(6) Uani 1 1 d . . . . .
P1 P 0.33257(6) 0.75053(5) 1.00491(5) 0.03255(19) Uani 1 1 d . . . . .
P2 P 0.68552(6) 0.56002(5) 0.13225(5) 0.03265(19) Uani 1 1 d . . . . .
P3 P 0.35169(6) 0.69318(6) 0.27958(5) 0.0355(2) Uani 1 1 d . . . . .
S1 S 0.71522(6) 0.69326(6) 0.73171(6) 0.0421(2) Uani 1 1 d . . . . .
C33A C 0.5897(10) 0.7938(11) 0.3770(10) 0.074(6) Uani 0.333(12) 1 d . . P A 2
H33D H 0.6336 0.7804 0.4264 0.111 Uiso 0.333(12) 1 calc R U P A 2
H33E H 0.6139 0.8459 0.3319 0.111 Uiso 0.333(12) 1 calc R U P A 2
H33F H 0.5937 0.7344 0.3448 0.111 Uiso 0.333(12) 1 calc R U P A 2
C32A C 0.4687(18) 0.9091(10) 0.4751(10) 0.079(2) Uani 0.307(7) 1 d . . P A 2
H32D H 0.4022 0.9356 0.5107 0.119 Uiso 0.307(7) 1 calc R U P A 2
H32E H 0.4943 0.9603 0.4297 0.119 Uiso 0.307(7) 1 calc R U P A 2
H32F H 0.5190 0.8865 0.5181 0.119 Uiso 0.307(7) 1 calc R U P A 2
H31 H 0.450(2) 0.831(2) 0.371(2) 0.040(9) Uiso 1 1 d . . . . .
H1A H 0.356(3) 1.233(3) 1.083(3) 0.062(11) Uiso 1 1 d . . . . .
H1B H 0.446(3) 1.223(3) 1.000(2) 0.061(11) Uiso 1 1 d . . . . .
H1C H 0.333(3) 1.266(3) 0.995(3) 0.064(12) Uiso 1 1 d . . . . .


_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
C1 C2 1.394(4) . ?
C1 C6 1.397(4) . ?
C1 O1 1.413(3) . ?
C2 C3 1.395(4) . ?
C2 C10 1.528(4) . ?
C3 C4 1.374(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(4) . ?
C4 N1 1.479(4) . ?
C5 C6 1.396(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.523(4) . ?
C7 C8 1.527(4) . ?
C7 C9 1.530(5) . ?
C7 H7 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.510(5) . ?
C10 C12 1.517(5) . ?
C10 H10A 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.395(4) . ?
C13 C18 1.400(4) . ?
C13 O5 1.406(3) . ?
C14 C15 1.388(4) . ?
C14 C22 1.527(4) . ?
C15 C16 1.377(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.376(4) . ?
C16 N2 1.470(4) . ?
C17 C18 1.390(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.523(4) . ?
C19 C21 1.527(4) . ?
C19 C20 1.529(5) . ?
C19 H19 1.0000 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.524(5) . ?
C22 C24 1.532(5) . ?
C22 H22 1.0000 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C30 1.381(4) . ?
C25 C26 1.403(4) . ?
C25 O9 1.408(4) . ?
C26 C27 1.396(4) . ?
C26 C34 1.521(4) . ?
C27 C28 1.372(4) . ?
C27 H27 0.9500 . ?
C28 C29 1.374(4) . ?
C28 N3 1.471(4) . ?
C29 C30 1.389(4) . ?
C29 H29 0.9500 . ?
C30 C31 1.519(4) . ?
C31 C32A 1.359(14) . ?
C31 C33 1.456(8) . ?
C31 C32 1.647(8) . ?
C31 C33A 1.827(15) . ?
C31 H31 0.86(3) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 C36 1.516(6) . ?
C34 C35 1.527(6) . ?
C34 H34 1.0000 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 F1 1.292(5) . ?
C37 F2 1.321(5) . ?
C37 F3 1.324(4) . ?
C37 S1 1.807(4) . ?
N1 H1A 0.91(4) . ?
N1 H1B 0.99(4) . ?
N1 H1C 0.84(4) . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N2 H2C 0.9100 . ?
N3 H3A 0.9100 . ?
N3 H3B 0.9100 . ?
N3 H3C 0.9100 . ?
O1 P1 1.598(2) . ?
O2 P1 1.556(2) . ?
O2 H2 0.8400 . ?
O3 P1 1.5063(19) . ?
O4 P1 1.500(2) . ?
O5 P2 1.596(2) . ?
O6 P2 1.492(2) . ?
O7 P2 1.5072(19) . ?
O8 P2 1.562(2) . ?
O8 H8 0.8400 . ?
O9 P3 1.574(2) . ?
O10 P3 1.553(2) . ?
O10 H10 0.8400 . ?
O11 P3 1.481(2) . ?
O12 P3 1.540(2) . ?
O12 H12 0.8400 . ?
O13 H13A 0.8694 . ?
O13 H13B 0.8700 . ?
O14 S1 1.436(2) . ?
O15 S1 1.436(3) . ?
O16 S1 1.429(2) . ?
C33A H33D 0.9800 . ?
C33A H33E 0.9800 . ?
C33A H33F 0.9800 . ?
C32A H32D 0.9800 . ?
C32A H32E 0.9800 . ?
C32A H32F 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
C2 C1 C6 123.6(3) . . ?
C2 C1 O1 118.1(2) . . ?
C6 C1 O1 118.2(2) . . ?
C1 C2 C3 117.0(3) . . ?
C1 C2 C10 121.4(3) . . ?
C3 C2 C10 121.6(3) . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 122.5(3) . . ?
C3 C4 N1 118.9(3) . . ?
C5 C4 N1 118.6(3) . . ?
C4 C5 C6 119.5(3) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 117.3(3) . . ?
C5 C6 C7 121.8(3) . . ?
C1 C6 C7 120.9(3) . . ?
C6 C7 C8 113.3(3) . . ?
C6 C7 C9 109.9(3) . . ?
C8 C7 C9 111.0(3) . . ?
C6 C7 H7 107.5 . . ?
C8 C7 H7 107.5 . . ?
C9 C7 H7 107.5 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C12 111.6(3) . . ?
C11 C10 C2 113.8(3) . . ?
C12 C10 C2 109.6(3) . . ?
C11 C10 H10A 107.2 . . ?
C12 C10 H10A 107.2 . . ?
C2 C10 H10A 107.2 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 123.2(3) . . ?
C14 C13 O5 118.8(2) . . ?
C18 C13 O5 117.9(2) . . ?
C15 C14 C13 117.5(3) . . ?
C15 C14 C22 120.1(3) . . ?
C13 C14 C22 122.4(3) . . ?
C16 C15 C14 120.0(3) . . ?
C16 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C17 C16 C15 122.1(3) . . ?
C17 C16 N2 118.3(2) . . ?
C15 C16 N2 119.5(2) . . ?
C16 C17 C18 119.9(3) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C17 C18 C13 117.3(2) . . ?
C17 C18 C19 121.5(3) . . ?
C13 C18 C19 121.1(2) . . ?
C18 C19 C21 113.7(2) . . ?
C18 C19 C20 110.8(3) . . ?
C21 C19 C20 109.9(3) . . ?
C18 C19 H19 107.4 . . ?
C21 C19 H19 107.4 . . ?
C20 C19 H19 107.4 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C14 112.6(3) . . ?
C23 C22 C24 111.1(3) . . ?
C14 C22 C24 109.7(3) . . ?
C23 C22 H22 107.7 . . ?
C14 C22 H22 107.7 . . ?
C24 C22 H22 107.7 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C30 C25 C26 123.9(3) . . ?
C30 C25 O9 118.3(3) . . ?
C26 C25 O9 117.8(3) . . ?
C27 C26 C25 116.4(3) . . ?
C27 C26 C34 122.7(3) . . ?
C25 C26 C34 120.9(3) . . ?
C28 C27 C26 120.4(3) . . ?
C28 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?
C27 C28 C29 121.7(3) . . ?
C27 C28 N3 119.8(3) . . ?
C29 C28 N3 118.5(3) . . ?
C28 C29 C30 120.2(3) . . ?
C28 C29 H29 119.9 . . ?
C30 C29 H29 119.9 . . ?
C25 C30 C29 117.4(3) . . ?
C25 C30 C31 121.6(3) . . ?
C29 C30 C31 121.0(3) . . ?
C32A C31 C30 119.2(7) . . ?
C33 C31 C30 114.9(4) . . ?
C33 C31 C32 108.8(5) . . ?
C30 C31 C32 105.2(4) . . ?
C32A C31 C33A 99.9(12) . . ?
C30 C31 C33A 101.7(5) . . ?
C32A C31 H31 130(2) . . ?
C33 C31 H31 115(2) . . ?
C30 C31 H31 110(2) . . ?
C32 C31 H31 102(2) . . ?
C33A C31 H31 78(2) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C36 C34 C26 112.8(3) . . ?
C36 C34 C35 111.2(4) . . ?
C26 C34 C35 110.8(3) . . ?
C36 C34 H34 107.3 . . ?
C26 C34 H34 107.3 . . ?
C35 C34 H34 107.3 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C34 C36 H36A 109.5 . . ?
C34 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C34 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
F1 C37 F2 106.8(4) . . ?
F1 C37 F3 109.8(4) . . ?
F2 C37 F3 106.2(3) . . ?
F1 C37 S1 111.5(3) . . ?
F2 C37 S1 111.3(3) . . ?
F3 C37 S1 111.0(3) . . ?
C4 N1 H1A 110(2) . . ?
C4 N1 H1B 111(2) . . ?
H1A N1 H1B 109(3) . . ?
C4 N1 H1C 112(3) . . ?
H1A N1 H1C 103(3) . . ?
H1B N1 H1C 112(3) . . ?
C16 N2 H2A 109.5 . . ?
C16 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C16 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C28 N3 H3A 109.5 . . ?
C28 N3 H3B 109.5 . . ?
H3A N3 H3B 109.5 . . ?
C28 N3 H3C 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
C1 O1 P1 123.85(18) . . ?
P1 O2 H2 109.5 . . ?
C13 O5 P2 125.49(17) . . ?
P2 O8 H8 109.5 . . ?
C25 O9 P3 123.53(18) . . ?
P3 O10 H10 109.5 . . ?
P3 O12 H12 109.5 . . ?
H13A O13 H13B 109.5 . . ?
O4 P1 O3 114.98(11) . . ?
O4 P1 O2 111.30(12) . . ?
O3 P1 O2 111.35(11) . . ?
O4 P1 O1 108.37(11) . . ?
O3 P1 O1 108.32(11) . . ?
O2 P1 O1 101.58(12) . . ?
O6 P2 O7 117.67(12) . . ?
O6 P2 O8 107.69(12) . . ?
O7 P2 O8 110.06(11) . . ?
O6 P2 O5 110.37(11) . . ?
O7 P2 O5 106.90(11) . . ?
O8 P2 O5 103.20(12) . . ?
O11 P3 O12 114.96(13) . . ?
O11 P3 O10 112.61(12) . . ?
O12 P3 O10 109.23(12) . . ?
O11 P3 O9 111.41(12) . . ?
O12 P3 O9 103.04(12) . . ?
O10 P3 O9 104.70(12) . . ?
O16 S1 O15 113.34(17) . . ?
O16 S1 O14 114.51(14) . . ?
O15 S1 O14 113.75(16) . . ?
O16 S1 C37 103.29(17) . . ?
O15 S1 C37 104.17(19) . . ?
O14 S1 C37 106.33(17) . . ?
C31 C33A H33D 109.5 . . ?
C31 C33A H33E 109.5 . . ?
H33D C33A H33E 109.5 . . ?
C31 C33A H33F 109.5 . . ?
H33D C33A H33F 109.5 . . ?
H33E C33A H33F 109.5 . . ?
C31 C32A H32D 109.5 . . ?
C31 C32A H32E 109.5 . . ?
H32D C32A H32E 109.5 . . ?
C31 C32A H32F 109.5 . . ?
H32D C32A H32F 109.5 . . ?
H32E C32A H32F 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
C6 C1 C2 C3 0.0(4) . . . . ?
O1 C1 C2 C3 -177.1(2) . . . . ?
C6 C1 C2 C10 178.7(3) . . . . ?
O1 C1 C2 C10 1.6(4) . . . . ?
C1 C2 C3 C4 -1.0(4) . . . . ?
C10 C2 C3 C4 -179.7(3) . . . . ?
C2 C3 C4 C5 0.9(5) . . . . ?
C2 C3 C4 N1 -178.5(3) . . . . ?
C3 C4 C5 C6 0.1(5) . . . . ?
N1 C4 C5 C6 179.5(3) . . . . ?
C4 C5 C6 C1 -1.1(4) . . . . ?
C4 C5 C6 C7 178.1(3) . . . . ?
C2 C1 C6 C5 1.0(4) . . . . ?
O1 C1 C6 C5 178.1(2) . . . . ?
C2 C1 C6 C7 -178.1(3) . . . . ?
O1 C1 C6 C7 -1.1(4) . . . . ?
C5 C6 C7 C8 17.4(4) . . . . ?
C1 C6 C7 C8 -163.5(3) . . . . ?
C5 C6 C7 C9 -107.4(3) . . . . ?
C1 C6 C7 C9 71.7(4) . . . . ?
C1 C2 C10 C11 151.4(3) . . . . ?
C3 C2 C10 C11 -29.9(4) . . . . ?
C1 C2 C10 C12 -82.9(4) . . . . ?
C3 C2 C10 C12 95.8(4) . . . . ?
C18 C13 C14 C15 1.2(4) . . . . ?
O5 C13 C14 C15 178.0(3) . . . . ?
C18 C13 C14 C22 -179.7(3) . . . . ?
O5 C13 C14 C22 -3.0(4) . . . . ?
C13 C14 C15 C16 0.5(4) . . . . ?
C22 C14 C15 C16 -178.6(3) . . . . ?
C14 C15 C16 C17 -1.2(5) . . . . ?
C14 C15 C16 N2 180.0(3) . . . . ?
C15 C16 C17 C18 0.3(4) . . . . ?
N2 C16 C17 C18 179.1(3) . . . . ?
C16 C17 C18 C13 1.3(4) . . . . ?
C16 C17 C18 C19 -176.7(3) . . . . ?
C14 C13 C18 C17 -2.1(4) . . . . ?
O5 C13 C18 C17 -178.9(2) . . . . ?
C14 C13 C18 C19 175.9(3) . . . . ?
O5 C13 C18 C19 -0.9(4) . . . . ?
C17 C18 C19 C21 -18.8(4) . . . . ?
C13 C18 C19 C21 163.3(3) . . . . ?
C17 C18 C19 C20 105.6(3) . . . . ?
C13 C18 C19 C20 -72.3(4) . . . . ?
C15 C14 C22 C23 -47.1(4) . . . . ?
C13 C14 C22 C23 133.9(3) . . . . ?
C15 C14 C22 C24 77.2(4) . . . . ?
C13 C14 C22 C24 -101.8(3) . . . . ?
C30 C25 C26 C27 -1.7(4) . . . . ?
O9 C25 C26 C27 -178.4(2) . . . . ?
C30 C25 C26 C34 176.1(3) . . . . ?
O9 C25 C26 C34 -0.6(4) . . . . ?
C25 C26 C27 C28 1.4(4) . . . . ?
C34 C26 C27 C28 -176.3(3) . . . . ?
C26 C27 C28 C29 -0.2(5) . . . . ?
C26 C27 C28 N3 179.4(3) . . . . ?
C27 C28 C29 C30 -0.9(5) . . . . ?
N3 C28 C29 C30 179.5(3) . . . . ?
C26 C25 C30 C29 0.6(5) . . . . ?
O9 C25 C30 C29 177.3(3) . . . . ?
C26 C25 C30 C31 -176.9(3) . . . . ?
O9 C25 C30 C31 -0.2(5) . . . . ?
C28 C29 C30 C25 0.7(5) . . . . ?
C28 C29 C30 C31 178.3(3) . . . . ?
C25 C30 C31 C32A 139.5(12) . . . . ?
C29 C30 C31 C32A -38.0(13) . . . . ?
C25 C30 C31 C33 -161.6(5) . . . . ?
C29 C30 C31 C33 20.9(7) . . . . ?
C25 C30 C31 C32 78.7(4) . . . . ?
C29 C30 C31 C32 -98.7(4) . . . . ?
C25 C30 C31 C33A -111.9(6) . . . . ?
C29 C30 C31 C33A 70.6(7) . . . . ?
C27 C26 C34 C36 -18.4(5) . . . . ?
C25 C26 C34 C36 164.0(3) . . . . ?
C27 C26 C34 C35 106.9(4) . . . . ?
C25 C26 C34 C35 -70.7(4) . . . . ?
C2 C1 O1 P1 -92.9(3) . . . . ?
C6 C1 O1 P1 89.9(3) . . . . ?
C14 C13 O5 P2 93.9(3) . . . . ?
C18 C13 O5 P2 -89.2(3) . . . . ?
C30 C25 O9 P3 92.1(3) . . . . ?
C26 C25 O9 P3 -91.0(3) . . . . ?
C1 O1 P1 O4 -3.1(2) . . . . ?
C1 O1 P1 O3 122.3(2) . . . . ?
C1 O1 P1 O2 -120.4(2) . . . . ?
C13 O5 P2 O6 -6.7(2) . . . . ?
C13 O5 P2 O7 122.4(2) . . . . ?
C13 O5 P2 O8 -121.5(2) . . . . ?
C25 O9 P3 O11 9.2(3) . . . . ?
C25 O9 P3 O12 133.0(2) . . . . ?
C25 O9 P3 O10 -112.7(2) . . . . ?
F1 C37 S1 O16 66.6(3) . . . . ?
F2 C37 S1 O16 -174.2(3) . . . . ?
F3 C37 S1 O16 -56.1(3) . . . . ?
F1 C37 S1 O15 -174.7(3) . . . . ?
F2 C37 S1 O15 -55.5(3) . . . . ?
F3 C37 S1 O15 62.5(3) . . . . ?
F1 C37 S1 O14 -54.3(4) . . . . ?
F2 C37 S1 O14 65.0(3) . . . . ?
F3 C37 S1 O14 -177.0(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
C3 H3 O16 0.95 2.58 3.330(4) 135.9 2_677
C29 H29 O15 0.95 2.53 3.309(4) 138.9 .
N2 H2A O14 0.91 2.05 2.938(3) 166.5 2_766
N2 H2A S1 0.91 2.79 3.566(2) 144.3 2_766
N2 H2C O6 0.91 1.84 2.748(3) 175.2 2_765
N2 H2B O3 0.91 1.89 2.801(3) 176.4 1_654
O8 H8 O11 0.84 1.81 2.628(3) 164.6 .
O10 H10 O4 0.84 1.71 2.551(3) 176.2 1_554
O12 H12 O3 0.84 1.71 2.536(3) 169.4 1_554

_refine_diff_density_max         0.426
_refine_diff_density_min         -0.597
_refine_diff_density_rms         0.062

####################################################################### 
# 
# 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_1C
_database_code_depnum_ccdc_archive 'CCDC 1510996'
_audit_update_record             
;
2016-12-19 deposited with the CCDC.
2017-01-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '3(C12 H20 N O4 P), H2 O'
_chemical_formula_sum            'C36 H62 N3 O13 P3'
_chemical_formula_weight         837.79

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           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                   18.824(11)
_cell_length_b                   34.10(2)
_cell_length_c                   16.321(11)
_cell_angle_alpha                90
_cell_angle_beta                 91.078(11)
_cell_angle_gamma                90
_cell_volume                     10475(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9694
_cell_measurement_theta_min      2.1710
_cell_measurement_theta_max      28.7310

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.063
_exptl_crystal_F_000             3584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.165
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.61397
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            37522
_diffrn_reflns_av_unetI/netI     0.0905
_diffrn_reflns_av_R_equivalents  0.0964
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_k_max       40
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.427
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             9206
_reflns_number_gt                6264
_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.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_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)+(0.1294P)²] 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         9206
_refine_ls_number_parameters     526
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1222
_refine_ls_R_factor_gt           0.0912
_refine_ls_wR_factor_ref         0.2710
_refine_ls_wR_factor_gt          0.2416
_refine_ls_goodness_of_fit_ref   1.100
_refine_ls_restrained_S_all      1.100
_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
P1 P 0.63688(6) 0.42372(3) 0.64387(7) 0.0488(3) Uani 1 1 d . . . . .
P2 P 0.93151(6) 0.26945(3) 0.35787(7) 0.0502(3) Uani 1 1 d . . . . .
P3 P 0.30032(6) 0.35744(3) 0.63732(7) 0.0494(3) Uani 1 1 d D . . . .
O1 O 0.67272(15) 0.43986(8) 0.56084(18) 0.0543(8) Uani 1 1 d . . . . .
O2 O 0.62289(17) 0.38077(8) 0.6288(2) 0.0622(9) Uani 1 1 d . . . . .
O3 O 0.57159(15) 0.44711(8) 0.66157(19) 0.0569(8) Uani 1 1 d . . . . .
O4 O 0.69551(17) 0.43075(8) 0.7095(2) 0.0631(9) Uani 1 1 d . . . . .
H4 H 0.6953 0.4544 0.7236 0.095 Uiso 1 1 calc R U . . .
O5 O 0.93226(16) 0.29394(8) 0.44250(18) 0.0528(7) Uani 1 1 d . . . . .
O6 O 0.86079(16) 0.25064(9) 0.34283(19) 0.0593(8) Uani 1 1 d . . . . .
O7 O 0.94769(19) 0.30033(9) 0.2932(2) 0.0622(8) Uani 1 1 d D . . . .
O8 O 0.99393(16) 0.24105(8) 0.36782(19) 0.0562(8) Uani 1 1 d . . . . .
O9 O 0.26103(15) 0.36544(7) 0.55046(17) 0.0501(7) Uani 1 1 d . . . . .
O10 O 0.29370(17) 0.31517(8) 0.6591(2) 0.0609(8) Uani 1 1 d . . . . .
O11 O 0.25661(18) 0.38234(10) 0.6969(2) 0.0682(9) Uani 1 1 d D . . . .
O12 O 0.37585(16) 0.37235(8) 0.62921(19) 0.0572(8) Uani 1 1 d . . . . .
O13 O 0.4962(2) 0.66242(12) 0.3412(3) 0.0854(12) Uani 1 1 d D . . . .
N1 N 0.57045(18) 0.55409(9) 0.3411(2) 0.0476(8) Uani 1 1 d . . . . .
H1A H 0.5877 0.5500 0.2901 0.057 Uiso 1 1 calc R U . . .
H1B H 0.5838 0.5783 0.3590 0.057 Uiso 1 1 calc R U . . .
H1C H 0.5222 0.5525 0.3391 0.057 Uiso 1 1 calc R U . . .
N2 N 0.70976(19) 0.31817(10) 0.6615(2) 0.0526(9) Uani 1 1 d . . . . .
H2A H 0.6829 0.3390 0.6452 0.063 Uiso 1 1 calc R U . . .
H2B H 0.7273 0.3225 0.7130 0.063 Uiso 1 1 calc R U . . .
H2C H 0.6825 0.2961 0.6612 0.063 Uiso 1 1 calc R U . . .
N3 N 0.13817(18) 0.25350(9) 0.3391(2) 0.0499(9) Uani 1 1 d . . . . .
H3A H 0.1436 0.2612 0.2862 0.060 Uiso 1 1 calc R U . . .
H3B H 0.0911 0.2510 0.3496 0.060 Uiso 1 1 calc R U . . .
H3C H 0.1602 0.2300 0.3472 0.060 Uiso 1 1 calc R U . . .
C1 C 0.6446(2) 0.46859(12) 0.5087(3) 0.0458(10) Uani 1 1 d . . . . .
C2 C 0.6036(2) 0.45636(12) 0.4405(3) 0.0493(10) Uani 1 1 d . . . . .
C3 C 0.5795(2) 0.48570(11) 0.3865(3) 0.0477(10) Uani 1 1 d . . . . .
H3 H 0.5492 0.4789 0.3414 0.057 Uiso 1 1 calc R U . . .
C4 C 0.5991(2) 0.52399(12) 0.3979(3) 0.0464(10) Uani 1 1 d . . . . .
C5 C 0.6408(3) 0.53549(13) 0.4646(3) 0.0583(12) Uani 1 1 d . . . . .
H5 H 0.6533 0.5623 0.4715 0.070 Uiso 1 1 calc R U . . .
C6 C 0.6644(2) 0.50751(12) 0.5217(3) 0.0532(11) Uani 1 1 d . . . . .
C7 C 0.5832(3) 0.41392(12) 0.4288(3) 0.0546(11) Uani 1 1 d . . . . .
H7 H 0.6182 0.3976 0.4607 0.065 Uiso 1 1 calc R U . . .
C8 C 0.5100(3) 0.40610(14) 0.4631(3) 0.0713(14) Uani 1 1 d . . . . .
H8A H 0.4977 0.3784 0.4549 0.107 Uiso 1 1 calc R U . . .
H8B H 0.5103 0.4122 0.5218 0.107 Uiso 1 1 calc R U . . .
H8C H 0.4749 0.4226 0.4346 0.107 Uiso 1 1 calc R U . . .
C9 C 0.5862(4) 0.40107(14) 0.3385(3) 0.0787(16) Uani 1 1 d . . . . .
H9A H 0.5726 0.3734 0.3338 0.118 Uiso 1 1 calc R U . . .
H9B H 0.5533 0.4171 0.3054 0.118 Uiso 1 1 calc R U . . .
H9C H 0.6346 0.4045 0.3186 0.118 Uiso 1 1 calc R U . . .
C10 C 0.7092(3) 0.51941(17) 0.5955(4) 0.086(2) Uani 1 1 d . . . . .
H10 H 0.7243 0.4938 0.6198 0.103 Uiso 0.544(9) 1 calc R U P A 1
C11 C 0.6604(5) 0.5375(2) 0.6627(4) 0.125(3) Uani 1 1 d . . . . .
H11A H 0.6372 0.5611 0.6411 0.187 Uiso 1 1 calc R U . . .
H11B H 0.6894 0.5443 0.7112 0.187 Uiso 1 1 calc R U . . .
H11C H 0.6243 0.5183 0.6779 0.187 Uiso 1 1 calc R U . . .
C12 C 0.7853(6) 0.5379(4) 0.5586(8) 0.084(3) Uani 0.544(9) 1 d . . P A 1
H12A H 0.8083 0.5182 0.5245 0.126 Uiso 0.544(9) 1 calc R U P A 1
H12B H 0.8172 0.5451 0.6043 0.126 Uiso 0.544(9) 1 calc R U P A 1
H12C H 0.7746 0.5612 0.5255 0.126 Uiso 0.544(9) 1 calc R U P A 1
C13 C 0.8747(2) 0.29977(11) 0.4955(3) 0.0483(10) Uani 1 1 d . . . . .
C14 C 0.8305(3) 0.33199(12) 0.4831(3) 0.0537(11) Uani 1 1 d . . . . .
C15 C 0.7761(3) 0.33846(12) 0.5403(3) 0.0533(11) Uani 1 1 d . . . . .
H15 H 0.7448 0.3601 0.5343 0.064 Uiso 1 1 calc R U . . .
C16 C 0.7695(2) 0.31299(12) 0.6044(3) 0.0507(10) Uani 1 1 d . . . . .
C17 C 0.8141(2) 0.28138(12) 0.6165(3) 0.0495(10) Uani 1 1 d . . . . .
H17 H 0.8075 0.2644 0.6619 0.059 Uiso 1 1 calc R U . . .
C18 C 0.8690(2) 0.27413(12) 0.5622(3) 0.0491(10) Uani 1 1 d . . . . .
C19 C 0.8387(3) 0.35949(14) 0.4096(3) 0.0706(14) Uani 1 1 d . . . . .
H19 H 0.8859 0.3539 0.3852 0.085 Uiso 1 1 calc R U . . .
C20 C 0.8388(5) 0.40278(15) 0.4364(5) 0.128(3) Uani 1 1 d . . . . .
H20A H 0.8758 0.4069 0.4786 0.191 Uiso 1 1 calc R U . . .
H20B H 0.8484 0.4195 0.3890 0.191 Uiso 1 1 calc R U . . .
H20C H 0.7924 0.4095 0.4586 0.191 Uiso 1 1 calc R U . . .
C21 C 0.7822(3) 0.3513(2) 0.3439(4) 0.0942(19) Uani 1 1 d . . . . .
H21A H 0.7886 0.3693 0.2977 0.141 Uiso 1 1 calc R U . . .
H21B H 0.7866 0.3242 0.3249 0.141 Uiso 1 1 calc R U . . .
H21C H 0.7349 0.3553 0.3668 0.141 Uiso 1 1 calc R U . . .
C22 C 0.9190(2) 0.23964(12) 0.5748(3) 0.0529(11) Uani 1 1 d . . . . .
H22 H 0.9630 0.2451 0.5433 0.063 Uiso 1 1 calc R U . . .
C23 C 0.9413(3) 0.23395(15) 0.6644(3) 0.0707(14) Uani 1 1 d . . . . .
H23A H 0.9734 0.2114 0.6691 0.106 Uiso 1 1 calc R U . . .
H23B H 0.9657 0.2576 0.6844 0.106 Uiso 1 1 calc R U . . .
H23C H 0.8991 0.2292 0.6972 0.106 Uiso 1 1 calc R U . . .
C24 C 0.8852(3) 0.20182(13) 0.5393(3) 0.0683(14) Uani 1 1 d . . . . .
H24A H 0.9179 0.1798 0.5478 0.102 Uiso 1 1 calc R U . . .
H24B H 0.8405 0.1964 0.5671 0.102 Uiso 1 1 calc R U . . .
H24C H 0.8757 0.2053 0.4805 0.102 Uiso 1 1 calc R U . . .
C25 C 0.2304(2) 0.33669(11) 0.4994(3) 0.0490(11) Uani 1 1 d . . . . .
C26 C 0.2718(2) 0.32178(11) 0.4357(3) 0.0486(10) Uani 1 1 d . . . . .
C27 C 0.2402(2) 0.29405(11) 0.3830(3) 0.0488(10) Uani 1 1 d . . . . .
H27 H 0.2665 0.2829 0.3397 0.059 Uiso 1 1 calc R U . . .
C28 C 0.1700(2) 0.28303(11) 0.3946(3) 0.0503(11) Uani 1 1 d . . . . .
C29 C 0.1297(3) 0.29869(13) 0.4569(3) 0.0552(11) Uani 1 1 d . . . . .
H29 H 0.0815 0.2910 0.4627 0.066 Uiso 1 1 calc R U . . .
C30 C 0.1601(2) 0.32573(12) 0.5109(3) 0.0508(10) Uani 1 1 d . . . . .
C31 C 0.3488(2) 0.33406(11) 0.4256(3) 0.0511(11) Uani 1 1 d . . . . .
H31 H 0.3562 0.3590 0.4567 0.061 Uiso 1 1 calc R U . . .
C32 C 0.3985(3) 0.30317(14) 0.4633(3) 0.0681(14) Uani 1 1 d . . . . .
H32A H 0.4480 0.3114 0.4565 0.102 Uiso 1 1 calc R U . . .
H32B H 0.3888 0.3004 0.5218 0.102 Uiso 1 1 calc R U . . .
H32C H 0.3907 0.2780 0.4357 0.102 Uiso 1 1 calc R U . . .
C33 C 0.3664(3) 0.34201(15) 0.3357(3) 0.0693(14) Uani 1 1 d . . . . .
H33A H 0.4163 0.3498 0.3319 0.104 Uiso 1 1 calc R U . . .
H33B H 0.3581 0.3182 0.3034 0.104 Uiso 1 1 calc R U . . .
H33C H 0.3359 0.3631 0.3144 0.104 Uiso 1 1 calc R U . . .
C34 C 0.1151(3) 0.34342(15) 0.5793(3) 0.0718(15) Uani 1 1 d . . . . .
H34 H 0.1453 0.3634 0.6083 0.086 Uiso 1 1 calc R U . . .
C35 C 0.0498(4) 0.3647(2) 0.5447(5) 0.126(3) Uani 1 1 d . . . . .
H35A H 0.0224 0.3756 0.5899 0.189 Uiso 1 1 calc R U . . .
H35B H 0.0649 0.3860 0.5087 0.189 Uiso 1 1 calc R U . . .
H35C H 0.0201 0.3462 0.5134 0.189 Uiso 1 1 calc R U . . .
C36 C 0.0973(5) 0.3110(2) 0.6432(5) 0.137(3) Uani 1 1 d . . . . .
H36A H 0.1414 0.2985 0.6628 0.206 Uiso 1 1 calc R U . . .
H36B H 0.0728 0.3228 0.6895 0.206 Uiso 1 1 calc R U . . .
H36C H 0.0665 0.2912 0.6173 0.206 Uiso 1 1 calc R U . . .
C12A C 0.7503(7) 0.5613(4) 0.5853(10) 0.084(3) Uani 0.456(9) 1 d . . P A 2
H12D H 0.7164 0.5812 0.5658 0.126 Uiso 0.456(9) 1 calc R U P A 2
H12E H 0.7883 0.5584 0.5456 0.126 Uiso 0.456(9) 1 calc R U P A 2
H12F H 0.7707 0.5693 0.6383 0.126 Uiso 0.456(9) 1 calc R U P A 2
H10A H 0.745(6) 0.495(3) 0.616(9) 0.101 Uiso 0.456(9) 1 d . U P A 2
H13A H 0.491(4) 0.6871(7) 0.347(5) 0.12(3) Uiso 1 1 d D . . . .
H13B H 0.463(3) 0.6470(18) 0.357(5) 0.14(3) Uiso 1 1 d D . . . .
H11 H 0.281(2) 0.3998(14) 0.720(4) 0.14(3) Uiso 1 1 d D . . . .
H7A H 0.935(6) 0.3235(13) 0.303(7) 0.24(5) Uiso 1 1 d D . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O3 1.498(3) . ?
P1 O2 1.507(3) . ?
P1 O4 1.542(3) . ?
P1 O1 1.621(3) . ?
P2 O6 1.494(3) . ?
P2 O7 1.526(3) . ?
P2 O8 1.529(3) . ?
P2 O5 1.614(3) . ?
P3 O10 1.490(3) . ?
P3 O12 1.518(3) . ?
P3 O11 1.541(3) . ?
P3 O9 1.610(3) . ?
O1 C1 1.395(5) . ?
O4 H4 0.8400 . ?
O5 C13 1.413(5) . ?
O7 H7A 0.84(2) . ?
O9 C25 1.403(5) . ?
O11 H11 0.838(19) . ?
O13 H13A 0.85(2) . ?
O13 H13B 0.86(2) . ?
N1 C4 1.478(5) . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
N2 C16 1.485(6) . ?
N2 H2A 0.9100 . ?
N2 H2B 0.9100 . ?
N2 H2C 0.9100 . ?
N3 C28 1.474(5) . ?
N3 H3A 0.9100 . ?
N3 H3B 0.9100 . ?
N3 H3C 0.9100 . ?
C1 C6 1.393(6) . ?
C1 C2 1.406(6) . ?
C2 C3 1.404(6) . ?
C2 C7 1.509(6) . ?
C3 C4 1.369(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(6) . ?
C5 C6 1.401(6) . ?
C5 H5 0.9500 . ?
C6 C10 1.512(6) . ?
C7 C8 1.520(7) . ?
C7 C9 1.541(6) . ?
C7 H7 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.569(10) . ?
C10 C12A 1.633(14) . ?
C10 C12 1.687(13) . ?
C10 H10 1.0000 . ?
C10 H10A 1.11(12) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.391(6) . ?
C13 C18 1.401(6) . ?
C14 C15 1.416(7) . ?
C14 C19 1.532(6) . ?
C15 C16 1.367(6) . ?
C15 H15 0.9500 . ?
C16 C17 1.378(6) . ?
C17 C18 1.397(6) . ?
C17 H17 0.9500 . ?
C18 C22 1.518(6) . ?
C19 C21 1.523(8) . ?
C19 C20 1.540(7) . ?
C19 H19 1.0000 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.526(6) . ?
C22 C24 1.546(6) . ?
C22 H22 1.0000 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C30 1.392(6) . ?
C25 C26 1.406(6) . ?
C26 C27 1.403(6) . ?
C26 C31 1.521(6) . ?
C27 C28 1.390(6) . ?
C27 H27 0.9500 . ?
C28 C29 1.386(6) . ?
C29 C30 1.391(6) . ?
C29 H29 0.9500 . ?
C30 C34 1.537(7) . ?
C31 C32 1.531(6) . ?
C31 C33 1.535(6) . ?
C31 H31 1.0000 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?
C34 C35 1.527(9) . ?
C34 C36 1.561(9) . ?
C34 H34 1.0000 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C12A H12D 0.9800 . ?
C12A H12E 0.9800 . ?
C12A H12F 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
O3 P1 O2 114.04(18) . . ?
O3 P1 O4 111.26(19) . . ?
O2 P1 O4 112.63(17) . . ?
O3 P1 O1 109.66(16) . . ?
O2 P1 O1 105.52(18) . . ?
O4 P1 O1 102.94(18) . . ?
O6 P2 O7 111.8(2) . . ?
O6 P2 O8 115.23(17) . . ?
O7 P2 O8 110.34(19) . . ?
O6 P2 O5 110.87(18) . . ?
O7 P2 O5 103.66(18) . . ?
O8 P2 O5 104.03(17) . . ?
O10 P3 O12 115.30(18) . . ?
O10 P3 O11 109.5(2) . . ?
O12 P3 O11 112.49(18) . . ?
O10 P3 O9 109.57(16) . . ?
O12 P3 O9 106.38(17) . . ?
O11 P3 O9 102.75(19) . . ?
C1 O1 P1 126.1(3) . . ?
P1 O4 H4 109.5 . . ?
C13 O5 P2 127.0(3) . . ?
P2 O7 H7A 117(8) . . ?
C25 O9 P3 125.5(2) . . ?
P3 O11 H11 112(2) . . ?
H13A O13 H13B 119(7) . . ?
C4 N1 H1A 109.5 . . ?
C4 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C4 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C16 N2 H2A 109.5 . . ?
C16 N2 H2B 109.5 . . ?
H2A N2 H2B 109.5 . . ?
C16 N2 H2C 109.5 . . ?
H2A N2 H2C 109.5 . . ?
H2B N2 H2C 109.5 . . ?
C28 N3 H3A 109.5 . . ?
C28 N3 H3B 109.5 . . ?
H3A N3 H3B 109.5 . . ?
C28 N3 H3C 109.5 . . ?
H3A N3 H3C 109.5 . . ?
H3B N3 H3C 109.5 . . ?
C6 C1 O1 118.6(4) . . ?
C6 C1 C2 123.0(4) . . ?
O1 C1 C2 118.1(4) . . ?
C3 C2 C1 116.9(4) . . ?
C3 C2 C7 121.7(4) . . ?
C1 C2 C7 121.3(4) . . ?
C4 C3 C2 120.7(4) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 121.6(4) . . ?
C3 C4 N1 118.9(4) . . ?
C5 C4 N1 119.4(4) . . ?
C4 C5 C6 119.9(4) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 H5 120.1 . . ?
C1 C6 C5 117.8(4) . . ?
C1 C6 C10 121.4(4) . . ?
C5 C6 C10 120.8(4) . . ?
C2 C7 C8 110.6(4) . . ?
C2 C7 C9 112.3(4) . . ?
C8 C7 C9 110.6(4) . . ?
C2 C7 H7 107.7 . . ?
C8 C7 H7 107.7 . . ?
C9 C7 H7 107.7 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 C11 109.7(5) . . ?
C6 C10 C12A 114.3(6) . . ?
C11 C10 C12A 90.7(8) . . ?
C6 C10 C12 106.3(6) . . ?
C11 C10 C12 127.9(7) . . ?
C6 C10 H10 103.4 . . ?
C11 C10 H10 103.4 . . ?
C12 C10 H10 103.4 . . ?
C6 C10 H10A 111(7) . . ?
C11 C10 H10A 116(7) . . ?
C12A C10 H10A 113(6) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C18 123.5(4) . . ?
C14 C13 O5 119.1(4) . . ?
C18 C13 O5 117.2(4) . . ?
C13 C14 C15 117.7(4) . . ?
C13 C14 C19 121.9(4) . . ?
C15 C14 C19 120.4(4) . . ?
C16 C15 C14 118.9(4) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C15 C16 C17 122.8(4) . . ?
C15 C16 N2 119.0(4) . . ?
C17 C16 N2 118.0(4) . . ?
C16 C17 C18 120.3(4) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C17 C18 C13 116.8(4) . . ?
C17 C18 C22 121.0(4) . . ?
C13 C18 C22 122.2(4) . . ?
C21 C19 C14 111.1(4) . . ?
C21 C19 C20 111.9(5) . . ?
C14 C19 C20 111.4(5) . . ?
C21 C19 H19 107.4 . . ?
C14 C19 H19 107.4 . . ?
C20 C19 H19 107.4 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18 C22 C23 112.8(4) . . ?
C18 C22 C24 110.2(4) . . ?
C23 C22 C24 110.9(4) . . ?
C18 C22 H22 107.6 . . ?
C23 C22 H22 107.6 . . ?
C24 C22 H22 107.6 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C30 C25 O9 119.3(4) . . ?
C30 C25 C26 122.9(4) . . ?
O9 C25 C26 117.7(4) . . ?
C27 C26 C25 117.6(4) . . ?
C27 C26 C31 120.9(4) . . ?
C25 C26 C31 121.5(4) . . ?
C28 C27 C26 119.4(4) . . ?
C28 C27 H27 120.3 . . ?
C26 C27 H27 120.3 . . ?
C29 C28 C27 122.0(4) . . ?
C29 C28 N3 119.5(4) . . ?
C27 C28 N3 118.5(4) . . ?
C28 C29 C30 119.7(4) . . ?
C28 C29 H29 120.2 . . ?
C30 C29 H29 120.2 . . ?
C29 C30 C25 118.3(4) . . ?
C29 C30 C34 119.7(4) . . ?
C25 C30 C34 122.0(4) . . ?
C26 C31 C32 110.2(3) . . ?
C26 C31 C33 112.0(4) . . ?
C32 C31 C33 111.3(4) . . ?
C26 C31 H31 107.7 . . ?
C32 C31 H31 107.7 . . ?
C33 C31 H31 107.7 . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C35 C34 C30 111.6(5) . . ?
C35 C34 C36 113.7(6) . . ?
C30 C34 C36 109.6(5) . . ?
C35 C34 H34 107.2 . . ?
C30 C34 H34 107.2 . . ?
C36 C34 H34 107.2 . . ?
C34 C35 H35A 109.5 . . ?
C34 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C34 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C34 C36 H36A 109.5 . . ?
C34 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C34 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C10 C12A H12D 109.5 . . ?
C10 C12A H12E 109.5 . . ?
H12D C12A H12E 109.5 . . ?
C10 C12A H12F 109.5 . . ?
H12D C12A H12F 109.5 . . ?
H12E C12A H12F 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
O3 P1 O1 C1 -5.5(4) . . . . ?
O2 P1 O1 C1 117.7(3) . . . . ?
O4 P1 O1 C1 -124.0(3) . . . . ?
O6 P2 O5 C13 -3.4(4) . . . . ?
O7 P2 O5 C13 116.8(3) . . . . ?
O8 P2 O5 C13 -127.8(3) . . . . ?
O10 P3 O9 C25 -5.0(4) . . . . ?
O12 P3 O9 C25 120.2(3) . . . . ?
O11 P3 O9 C25 -121.4(3) . . . . ?
P1 O1 C1 C6 92.2(4) . . . . ?
P1 O1 C1 C2 -94.2(4) . . . . ?
C6 C1 C2 C3 -3.2(6) . . . . ?
O1 C1 C2 C3 -176.4(4) . . . . ?
C6 C1 C2 C7 -179.8(4) . . . . ?
O1 C1 C2 C7 7.0(6) . . . . ?
C1 C2 C3 C4 3.8(6) . . . . ?
C7 C2 C3 C4 -179.5(4) . . . . ?
C2 C3 C4 C5 -2.7(7) . . . . ?
C2 C3 C4 N1 -178.0(4) . . . . ?
C3 C4 C5 C6 0.7(7) . . . . ?
N1 C4 C5 C6 175.9(4) . . . . ?
O1 C1 C6 C5 174.4(4) . . . . ?
C2 C1 C6 C5 1.2(7) . . . . ?
O1 C1 C6 C10 -6.2(7) . . . . ?
C2 C1 C6 C10 -179.4(5) . . . . ?
C4 C5 C6 C1 0.1(7) . . . . ?
C4 C5 C6 C10 -179.3(5) . . . . ?
C3 C2 C7 C8 -81.8(5) . . . . ?
C1 C2 C7 C8 94.7(5) . . . . ?
C3 C2 C7 C9 42.4(6) . . . . ?
C1 C2 C7 C9 -141.1(5) . . . . ?
C1 C6 C10 C11 -100.5(6) . . . . ?
C5 C6 C10 C11 78.8(6) . . . . ?
C1 C6 C10 C12A 159.3(8) . . . . ?
C5 C6 C10 C12A -21.4(10) . . . . ?
C1 C6 C10 C12 117.7(7) . . . . ?
C5 C6 C10 C12 -62.9(8) . . . . ?
P2 O5 C13 C14 -89.7(4) . . . . ?
P2 O5 C13 C18 95.4(4) . . . . ?
C18 C13 C14 C15 -1.3(6) . . . . ?
O5 C13 C14 C15 -176.0(4) . . . . ?
C18 C13 C14 C19 179.6(4) . . . . ?
O5 C13 C14 C19 5.0(6) . . . . ?
C13 C14 C15 C16 -0.1(6) . . . . ?
C19 C14 C15 C16 178.9(4) . . . . ?
C14 C15 C16 C17 0.8(7) . . . . ?
C14 C15 C16 N2 -176.1(4) . . . . ?
C15 C16 C17 C18 0.0(6) . . . . ?
N2 C16 C17 C18 176.9(4) . . . . ?
C16 C17 C18 C13 -1.4(6) . . . . ?
C16 C17 C18 C22 179.5(4) . . . . ?
C14 C13 C18 C17 2.1(6) . . . . ?
O5 C13 C18 C17 176.8(3) . . . . ?
C14 C13 C18 C22 -178.9(4) . . . . ?
O5 C13 C18 C22 -4.1(6) . . . . ?
C13 C14 C19 C21 102.9(6) . . . . ?
C15 C14 C19 C21 -76.2(6) . . . . ?
C13 C14 C19 C20 -131.7(5) . . . . ?
C15 C14 C19 C20 49.3(7) . . . . ?
C17 C18 C22 C23 -41.5(6) . . . . ?
C13 C18 C22 C23 139.5(5) . . . . ?
C17 C18 C22 C24 83.1(5) . . . . ?
C13 C18 C22 C24 -95.9(5) . . . . ?
P3 O9 C25 C30 87.9(4) . . . . ?
P3 O9 C25 C26 -95.5(4) . . . . ?
C30 C25 C26 C27 -1.3(6) . . . . ?
O9 C25 C26 C27 -177.8(3) . . . . ?
C30 C25 C26 C31 -179.3(4) . . . . ?
O9 C25 C26 C31 4.3(6) . . . . ?
C25 C26 C27 C28 1.1(6) . . . . ?
C31 C26 C27 C28 179.0(4) . . . . ?
C26 C27 C28 C29 0.2(6) . . . . ?
C26 C27 C28 N3 -179.3(4) . . . . ?
C27 C28 C29 C30 -1.3(7) . . . . ?
N3 C28 C29 C30 178.2(4) . . . . ?
C28 C29 C30 C25 1.0(7) . . . . ?
C28 C29 C30 C34 179.3(4) . . . . ?
O9 C25 C30 C29 176.7(4) . . . . ?
C26 C25 C30 C29 0.3(6) . . . . ?
O9 C25 C30 C34 -1.6(6) . . . . ?
C26 C25 C30 C34 -178.0(4) . . . . ?
C27 C26 C31 C32 -79.6(5) . . . . ?
C25 C26 C31 C32 98.3(5) . . . . ?
C27 C26 C31 C33 44.9(5) . . . . ?
C25 C26 C31 C33 -137.2(4) . . . . ?
C29 C30 C34 C35 -58.7(6) . . . . ?
C25 C30 C34 C35 119.6(5) . . . . ?
C29 C30 C34 C36 68.2(7) . . . . ?
C25 C30 C34 C36 -113.6(6) . . . . ?

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
N1 H1A O3 0.91 2.12 2.930(5) 148.4 6_565
N1 H1A O4 0.91 2.53 3.258(5) 137.8 6_565
N1 H1B O12 0.91 1.85 2.744(4) 165.2 5_666
N1 H1C O3 0.91 1.77 2.674(5) 176.0 5_666
N3 H3A O6 0.91 2.14 2.972(5) 152.0 2_655
N3 H3A O7 0.91 2.52 3.114(5) 123.7 2_655
N3 H3B O8 0.91 1.89 2.796(5) 174.7 1_455
N3 H3C O10 0.91 1.77 2.670(5) 168.1 7_556
O13 H13A O8 0.85(2) 1.87(2) 2.717(5) 170(7) 3_455
O13 H13B O2 0.86(2) 1.89(3) 2.734(5) 167(8) 5_666
O11 H11 O4 0.838(19) 1.62(2) 2.412(4) 157(5) 2_656
N2 H2A O2 0.91 1.83 2.735(5) 170.8 .
N2 H2B O10 0.91 2.15 2.932(5) 144.1 2_656
N2 H2B O11 0.91 2.53 3.236(5) 134.9 2_656
N2 H2C O6 0.91 1.79 2.696(5) 172.4 7_656

_refine_diff_density_max         0.765
_refine_diff_density_min         -0.485
_refine_diff_density_rms         0.070


####################################################################### 
# 
# 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_6
_database_code_depnum_ccdc_archive 'CCDC 1511001'
_audit_update_record             
;
2016-12-19 deposited with the CCDC.
2017-01-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H28 N O5 P S'
_chemical_formula_sum            'C15 H28 N O5 P S'
_chemical_formula_weight         365.41

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                   8.1630(8)
_cell_length_b                   21.2184(19)
_cell_length_c                   11.3124(10)
_cell_angle_alpha                90
_cell_angle_beta                 102.267(9)
_cell_angle_gamma                90
_cell_volume                     1914.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3873
_cell_measurement_theta_min      2.5520
_cell_measurement_theta_max      29.6990

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_F_000             784
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.275
_shelx_estimated_absorpt_T_min   0.935
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.35781
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            14052
_diffrn_reflns_av_unetI/netI     0.0866
_diffrn_reflns_av_R_equivalents  0.0804
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.553
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3370
_reflns_number_gt                2004
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_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)+(0.0781P)²+2.9683P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3370
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1457
_refine_ls_R_factor_gt           0.0881
_refine_ls_wR_factor_ref         0.2271
_refine_ls_wR_factor_gt          0.1893
_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
C1 C 0.4365(6) 0.6123(2) 0.3886(4) 0.0420(12) Uani 1 1 d . . . . .
C2 C 0.4874(7) 0.6536(2) 0.4853(5) 0.0488(14) Uani 1 1 d . . . . .
C3 C 0.6432(7) 0.6441(3) 0.5598(4) 0.0474(13) Uani 1 1 d . . . . .
H3 H 0.6812 0.6717 0.6261 0.057 Uiso 1 1 calc R U . . .
C4 C 0.7422(6) 0.5959(2) 0.5389(4) 0.0435(13) Uani 1 1 d . . . . .
C5 C 0.6925(6) 0.5556(3) 0.4413(4) 0.0467(13) Uani 1 1 d . . . . .
H5 H 0.7640 0.5221 0.4283 0.056 Uiso 1 1 calc R U . . .
C6 C 0.5391(6) 0.5639(2) 0.3631(4) 0.0423(12) Uani 1 1 d . . . . .
C7 C 0.3806(8) 0.7095(3) 0.5066(6) 0.076(2) Uani 1 1 d . . . . .
H7 H 0.2707 0.7067 0.4475 0.091 Uiso 1 1 calc R U . . .
C8 C 0.3465(12) 0.7105(4) 0.6307(7) 0.129(4) Uani 1 1 d . . . . .
H8A H 0.2776 0.7473 0.6395 0.193 Uiso 1 1 calc R U . . .
H8B H 0.2867 0.6720 0.6442 0.193 Uiso 1 1 calc R U . . .
H8C H 0.4528 0.7129 0.6903 0.193 Uiso 1 1 calc R U . . .
C9 C 0.4659(12) 0.7709(3) 0.4826(8) 0.115(3) Uani 1 1 d . . . . .
H9A H 0.4881 0.7700 0.4008 0.172 Uiso 1 1 calc R U . . .
H9B H 0.3925 0.8066 0.4898 0.172 Uiso 1 1 calc R U . . .
H9C H 0.5720 0.7755 0.5417 0.172 Uiso 1 1 calc R U . . .
C10 C 0.4943(7) 0.5256(3) 0.2479(4) 0.0522(14) Uani 1 1 d . . . . .
H10 H 0.3701 0.5194 0.2266 0.063 Uiso 1 1 calc R U . . .
C11 C 0.5476(11) 0.5640(4) 0.1473(5) 0.101(3) Uani 1 1 d . . . . .
H11A H 0.4935 0.6055 0.1413 0.151 Uiso 1 1 calc R U . . .
H11B H 0.6697 0.5694 0.1664 0.151 Uiso 1 1 calc R U . . .
H11C H 0.5137 0.5418 0.0701 0.151 Uiso 1 1 calc R U . . .
C12 C 0.5790(8) 0.4618(3) 0.2557(5) 0.0720(19) Uani 1 1 d . . . . .
H12A H 0.5444 0.4397 0.1784 0.108 Uiso 1 1 calc R U . . .
H12B H 0.7009 0.4675 0.2739 0.108 Uiso 1 1 calc R U . . .
H12C H 0.5465 0.4369 0.3200 0.108 Uiso 1 1 calc R U . . .
C13 C -0.0560(10) 0.6890(4) 0.2821(8) 0.112(3) Uani 1 1 d . . . . .
H13A H -0.1580 0.7051 0.2288 0.168 Uiso 1 1 calc R U . . .
H13B H 0.0385 0.7168 0.2776 0.168 Uiso 1 1 calc R U . . .
H13C H -0.0719 0.6878 0.3656 0.168 Uiso 1 1 calc R U . . .
C14 C 0.1254(11) 0.5786(4) -0.0351(6) 0.103(3) Uani 1 1 d . . . . .
H14A H 0.0749 0.5456 -0.0920 0.155 Uiso 1 1 calc R U . . .
H14B H 0.1341 0.5636 0.0480 0.155 Uiso 1 1 calc R U . . .
H14C H 0.2374 0.5886 -0.0479 0.155 Uiso 1 1 calc R U . . .
C15 C -0.1828(10) 0.6055(5) -0.0546(7) 0.135(4) Uani 1 1 d . . . . .
H15A H -0.2777 0.6348 -0.0685 0.203 Uiso 1 1 calc R U . . .
H15B H -0.1723 0.5855 0.0248 0.203 Uiso 1 1 calc R U . . .
H15C H -0.2014 0.5730 -0.1176 0.203 Uiso 1 1 calc R U . . .
N1 N 0.9071(5) 0.5853(2) 0.6156(4) 0.0483(11) Uani 1 1 d . . . . .
H1A H 0.9861 0.5865 0.5697 0.058 Uiso 1 1 calc R U . . .
H1B H 0.9092 0.5470 0.6520 0.058 Uiso 1 1 calc R U . . .
H1C H 0.9290 0.6159 0.6732 0.058 Uiso 1 1 calc R U . . .
O1 O 0.2816(4) 0.62154(16) 0.3089(3) 0.0486(9) Uani 1 1 d . . . . .
O2 O -0.0223(5) 0.6278(2) 0.2454(4) 0.0743(13) Uani 1 1 d . . . . .
O3 O 0.0984(5) 0.52345(17) 0.2659(3) 0.0562(10) Uani 1 1 d . . . . .
O4 O 0.1096(4) 0.58774(19) 0.4576(3) 0.0619(11) Uani 1 1 d . . . . .
O5 O -0.0196(7) 0.6652(2) -0.1882(3) 0.0908(16) Uani 1 1 d . . . . .
P1 P 0.11451(18) 0.58532(7) 0.32774(13) 0.0525(5) Uani 1 1 d . . . . .
S1 S -0.0004(2) 0.64627(8) -0.05879(13) 0.0748(6) Uani 1 1 d . . . . .


_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
C1 C6 1.393(7) . ?
C1 C2 1.395(7) . ?
C1 O1 1.402(6) . ?
C2 C3 1.383(7) . ?
C2 C7 1.522(8) . ?
C3 C4 1.356(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.387(7) . ?
C4 N1 1.456(6) . ?
C5 C6 1.383(7) . ?
C5 H5 0.9500 . ?
C6 C10 1.514(7) . ?
C7 C8 1.489(10) . ?
C7 C9 1.529(10) . ?
C7 H7 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C12 1.514(8) . ?
C10 C11 1.536(8) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 O2 1.409(8) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 S1 1.753(8) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 S1 1.732(9) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
N1 H1A 0.9100 . ?
N1 H1B 0.9100 . ?
N1 H1C 0.9100 . ?
O1 P1 1.619(4) . ?
O2 P1 1.576(4) . ?
O3 P1 1.480(4) . ?
O4 P1 1.479(4) . ?
O5 S1 1.494(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
C6 C1 C2 122.2(5) . . ?
C6 C1 O1 118.1(4) . . ?
C2 C1 O1 119.6(5) . . ?
C3 C2 C1 118.0(5) . . ?
C3 C2 C7 120.0(5) . . ?
C1 C2 C7 121.9(5) . . ?
C4 C3 C2 120.5(5) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 121.3(5) . . ?
C3 C4 N1 121.5(4) . . ?
C5 C4 N1 117.2(5) . . ?
C6 C5 C4 120.1(5) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 117.7(5) . . ?
C5 C6 C10 120.2(5) . . ?
C1 C6 C10 121.9(5) . . ?
C8 C7 C2 112.9(6) . . ?
C8 C7 C9 109.8(7) . . ?
C2 C7 C9 109.8(6) . . ?
C8 C7 H7 108.1 . . ?
C2 C7 H7 108.1 . . ?
C9 C7 H7 108.1 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C12 C10 C6 113.9(4) . . ?
C12 C10 C11 108.7(5) . . ?
C6 C10 C11 107.3(5) . . ?
C12 C10 H10 108.9 . . ?
C6 C10 H10 108.9 . . ?
C11 C10 H10 108.9 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C13 H13A 109.5 . . ?
O2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
O2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
S1 C14 H14A 109.5 . . ?
S1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
S1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
S1 C15 H15A 109.5 . . ?
S1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
S1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C4 N1 H1A 109.5 . . ?
C4 N1 H1B 109.5 . . ?
H1A N1 H1B 109.5 . . ?
C4 N1 H1C 109.5 . . ?
H1A N1 H1C 109.5 . . ?
H1B N1 H1C 109.5 . . ?
C1 O1 P1 121.2(3) . . ?
C13 O2 P1 120.7(4) . . ?
O4 P1 O3 118.8(2) . . ?
O4 P1 O2 113.7(2) . . ?
O3 P1 O2 104.3(2) . . ?
O4 P1 O1 108.4(2) . . ?
O3 P1 O1 110.6(2) . . ?
O2 P1 O1 99.3(2) . . ?
O5 S1 C15 104.5(4) . . ?
O5 S1 C14 107.9(3) . . ?
C15 S1 C14 93.7(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
C6 C1 C2 C3 -2.1(8) . . . . ?
O1 C1 C2 C3 -178.0(4) . . . . ?
C6 C1 C2 C7 174.9(5) . . . . ?
O1 C1 C2 C7 -0.9(8) . . . . ?
C1 C2 C3 C4 -0.3(8) . . . . ?
C7 C2 C3 C4 -177.5(5) . . . . ?
C2 C3 C4 C5 1.5(8) . . . . ?
C2 C3 C4 N1 179.6(5) . . . . ?
C3 C4 C5 C6 -0.2(8) . . . . ?
N1 C4 C5 C6 -178.4(4) . . . . ?
C4 C5 C6 C1 -2.1(7) . . . . ?
C4 C5 C6 C10 172.0(5) . . . . ?
C2 C1 C6 C5 3.4(7) . . . . ?
O1 C1 C6 C5 179.3(4) . . . . ?
C2 C1 C6 C10 -170.7(5) . . . . ?
O1 C1 C6 C10 5.2(7) . . . . ?
C3 C2 C7 C8 -57.0(9) . . . . ?
C1 C2 C7 C8 126.0(7) . . . . ?
C3 C2 C7 C9 65.9(8) . . . . ?
C1 C2 C7 C9 -111.1(6) . . . . ?
C5 C6 C10 C12 28.2(7) . . . . ?
C1 C6 C10 C12 -157.9(5) . . . . ?
C5 C6 C10 C11 -92.2(6) . . . . ?
C1 C6 C10 C11 81.7(6) . . . . ?
C6 C1 O1 P1 89.6(5) . . . . ?
C2 C1 O1 P1 -94.4(5) . . . . ?
C13 O2 P1 O4 42.7(6) . . . . ?
C13 O2 P1 O3 173.6(6) . . . . ?
C13 O2 P1 O1 -72.2(6) . . . . ?
C1 O1 P1 O4 43.7(4) . . . . ?
C1 O1 P1 O3 -88.2(4) . . . . ?
C1 O1 P1 O2 162.6(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
N1 H1A O4 0.91 1.78 2.681(5) 169.8 1_655
N1 H1B O3 0.91 1.77 2.674(6) 173.6 3_666
N1 H1C O5 0.91 1.86 2.755(6) 168.7 1_656

_refine_diff_density_max         0.454
_refine_diff_density_min         -0.378
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_1D
_database_code_depnum_ccdc_archive 'CCDC 947941'
_audit_update_record             
;
2016-12-19 deposited with the CCDC.
2017-01-09 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H42 N2 O9 P2'
_chemical_formula_sum            'C24 H42 N2 O9 P2'
_chemical_formula_weight         564.53

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   11.778(3)
_cell_length_b                   14.601(4)
_cell_length_c                   16.488(4)
_cell_angle_alpha                90
_cell_angle_beta                 103.452(4)
_cell_angle_gamma                90
_cell_volume                     2757.7(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    17621
_cell_measurement_theta_min      2.2890
_cell_measurement_theta_max      31.2280

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_F_000             1208
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.211
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.87226
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (2x2 bin mode)
;
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_reflns_number            20206
_diffrn_reflns_av_unetI/netI     0.0240
_diffrn_reflns_av_R_equivalents  0.0268
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         3.309
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4841
_reflns_number_gt                4484
_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 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_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)+(0.0451P)²+0.7966P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4841
_refine_ls_number_parameters     502
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0361
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.0837
_refine_ls_wR_factor_gt          0.0811
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_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
P1 P 0.36381(3) 0.56603(3) 0.41827(2) 0.01420(12) Uani 1 1 d . . . . .
P2 P 0.54564(3) 0.13172(3) 0.07111(2) 0.01364(12) Uani 1 1 d . . . . .
O1 O 0.44163(9) 0.65016(7) 0.39753(6) 0.0159(2) Uani 1 1 d . . . . .
O2 O 0.24181(9) 0.57189(8) 0.36706(7) 0.0198(3) Uani 1 1 d . . . . .
O3 O 0.42031(10) 0.47788(8) 0.39118(7) 0.0188(3) Uani 1 1 d . . . . .
O4 O 0.38192(9) 0.57009(8) 0.51132(6) 0.0181(3) Uani 1 1 d . . . . .
O5 O 0.52665(9) 0.22423(7) 0.11854(6) 0.0157(2) Uani 1 1 d . . . . .
O6 O 0.66701(9) 0.09667(8) 0.10124(7) 0.0191(3) Uani 1 1 d . . . . .
O7 O 0.50472(9) 0.15286(8) -0.02007(6) 0.0178(3) Uani 1 1 d . . . . .
O8 O 0.46172(12) 0.06034(8) 0.09761(8) 0.0239(3) Uani 1 1 d . . . . .
N1 N 0.34037(13) 0.88357(10) 0.12129(9) 0.0169(3) Uani 1 1 d . . . . .
N2 N 0.78799(13) 0.41030(10) 0.39683(8) 0.0150(3) Uani 1 1 d . . . . .
C1 C 0.41560(13) 0.70781(11) 0.32730(9) 0.0146(3) Uani 1 1 d . . . . .
C2 C 0.36696(13) 0.79321(11) 0.33709(9) 0.0150(3) Uani 1 1 d . . . . .
C3 C 0.34254(14) 0.85067(12) 0.26793(10) 0.0164(3) Uani 1 1 d . . . . .
C4 C 0.36995(13) 0.82368(11) 0.19445(9) 0.0153(3) Uani 1 1 d . . . . .
C5 C 0.42548(14) 0.74228(11) 0.18800(10) 0.0165(3) Uani 1 1 d . . . . .
C6 C 0.45163(13) 0.68217(11) 0.25568(9) 0.0153(3) Uani 1 1 d . . . . .
C7 C 0.34636(15) 0.82396(12) 0.42089(10) 0.0188(4) Uani 1 1 d . . . . .
C8 C 0.37246(18) 0.92569(13) 0.43753(12) 0.0262(4) Uani 1 1 d . . . . .
C9 C 0.22279(17) 0.80206(15) 0.42813(13) 0.0299(4) Uani 1 1 d . . . . .
C10 C 0.51991(14) 0.59496(12) 0.25077(10) 0.0181(4) Uani 1 1 d . . . . .
C11 C 0.62310(16) 0.61266(14) 0.21125(12) 0.0257(4) Uani 1 1 d . . . . .
C12 C 0.44085(17) 0.51930(13) 0.20461(11) 0.0247(4) Uani 1 1 d . . . . .
C13 C 0.59803(13) 0.26469(11) 0.18878(9) 0.0137(3) Uani 1 1 d . . . . .
C14 C 0.68463(13) 0.32532(11) 0.17696(9) 0.0145(3) Uani 1 1 d . . . . .
C15 C 0.74913(14) 0.37160(11) 0.24679(10) 0.0151(3) Uani 1 1 d . . . . .
C16 C 0.72405(13) 0.35857(10) 0.32384(9) 0.0142(3) Uani 1 1 d . . . . .
C17 C 0.63802(13) 0.29894(11) 0.33411(9) 0.0156(3) Uani 1 1 d . . . . .
C18 C 0.57234(13) 0.25043(11) 0.26637(9) 0.0146(3) Uani 1 1 d . . . . .
C19 C 0.70107(15) 0.34356(12) 0.08981(10) 0.0186(4) Uani 1 1 d . . . . .
C20 C 0.6081(2) 0.41055(16) 0.04458(12) 0.0354(5) Uani 1 1 d . . . . .
C21 C 0.82316(18) 0.37638(15) 0.08860(12) 0.0293(4) Uani 1 1 d . . . . .
C22 C 0.47831(14) 0.18381(12) 0.27751(10) 0.0182(4) Uani 1 1 d . . . . .
C23 C 0.53279(19) 0.08993(14) 0.30077(13) 0.0299(4) Uani 1 1 d . . . . .
C24 C 0.41192(17) 0.21599(16) 0.34167(12) 0.0297(4) Uani 1 1 d . . . . .
O9 O 0.32023(12) 0.33415(9) 0.51472(8) 0.0268(3) Uani 1 1 d . . . . .
H5 H 0.4474(14) 0.7264(12) 0.1361(11) 0.017(4) Uiso 1 1 d . . . . .
H19 H 0.6873(14) 0.2867(13) 0.0611(10) 0.018(4) Uiso 1 1 d . . . . .
H3A H 0.3073(15) 0.9076(13) 0.2688(11) 0.020(5) Uiso 1 1 d . . . . .
H17 H 0.6230(14) 0.2931(11) 0.3900(10) 0.014(4) Uiso 1 1 d . . . . .
H15 H 0.8091(15) 0.4141(12) 0.2420(10) 0.016(4) Uiso 1 1 d . . . . .
H10 H 0.5510(15) 0.5743(12) 0.3081(11) 0.019(4) Uiso 1 1 d . . . . .
H7 H 0.4018(15) 0.7894(12) 0.4641(10) 0.017(4) Uiso 1 1 d . . . . .
H22 H 0.4235(15) 0.1817(12) 0.2255(11) 0.017(4) Uiso 1 1 d . . . . .
H1A H 0.3286(17) 0.9405(15) 0.1344(12) 0.028(5) Uiso 1 1 d . . . . .
H2A H 0.7426(17) 0.4146(12) 0.4306(11) 0.019(5) Uiso 1 1 d . . . . .
H1B H 0.3977(18) 0.8827(13) 0.0933(11) 0.028(5) Uiso 1 1 d . . . . .
H2B H 0.8046(16) 0.4675(15) 0.3848(11) 0.027(5) Uiso 1 1 d . . . . .
H2C H 0.8608(18) 0.3828(13) 0.4244(11) 0.026(5) Uiso 1 1 d . . . . .
H11A H 0.5951(17) 0.6299(13) 0.1508(13) 0.031(5) Uiso 1 1 d . . . . .
H12A H 0.4101(17) 0.5375(14) 0.1473(13) 0.031(5) Uiso 1 1 d . . . . .
H11B H 0.6709(18) 0.5581(15) 0.2145(12) 0.033(5) Uiso 1 1 d . . . . .
H12B H 0.3692(18) 0.5082(14) 0.2270(12) 0.036(5) Uiso 1 1 d . . . . .
H12C H 0.4842(17) 0.4587(15) 0.2075(12) 0.035(5) Uiso 1 1 d . . . . .
H11C H 0.6747(18) 0.6643(15) 0.2381(12) 0.038(6) Uiso 1 1 d . . . . .
H9A H 0.1663(19) 0.8352(15) 0.3853(14) 0.042(6) Uiso 1 1 d . . . . .
H9B H 0.2058(17) 0.7371(16) 0.4200(12) 0.036(6) Uiso 1 1 d . . . . .
H9C H 0.2117(17) 0.8227(14) 0.4858(12) 0.033(5) Uiso 1 1 d . . . . .
H8 H 0.404(2) 0.0784(17) 0.1024(15) 0.051(8) Uiso 1 1 d . . . . .
H24A H 0.4586(18) 0.2118(14) 0.3990(13) 0.035(5) Uiso 1 1 d . . . . .
H24B H 0.3441(19) 0.1758(15) 0.3399(12) 0.039(6) Uiso 1 1 d . . . . .
H24C H 0.3870(18) 0.2815(16) 0.3304(12) 0.039(6) Uiso 1 1 d . . . . .
H21A H 0.8358(18) 0.4384(16) 0.1093(13) 0.037(6) Uiso 1 1 d . . . . .
H21B H 0.8831(18) 0.3337(15) 0.1219(13) 0.037(6) Uiso 1 1 d . . . . .
H21C H 0.8315(17) 0.3795(14) 0.0304(13) 0.034(5) Uiso 1 1 d . . . . .
H8A H 0.3686(17) 0.9407(14) 0.4948(13) 0.034(5) Uiso 1 1 d . . . . .
H8B H 0.3135(17) 0.9649(15) 0.3978(12) 0.033(5) Uiso 1 1 d . . . . .
H8C H 0.4526(18) 0.9405(14) 0.4322(12) 0.033(5) Uiso 1 1 d . . . . .
H9D H 0.283(2) 0.3595(17) 0.5510(16) 0.057(8) Uiso 1 1 d . . . . .
H9E H 0.395(2) 0.3441(17) 0.5351(14) 0.052(7) Uiso 1 1 d . . . . .
H23A H 0.5755(17) 0.0684(14) 0.2595(12) 0.032(5) Uiso 1 1 d . . . . .
H23B H 0.5854(19) 0.0942(14) 0.3524(14) 0.036(6) Uiso 1 1 d . . . . .
H20A H 0.6154(17) 0.4195(14) -0.0124(13) 0.036(6) Uiso 1 1 d . . . . .
H20B H 0.6220(18) 0.4703(18) 0.0731(14) 0.047(6) Uiso 1 1 d . . . . .
H20C H 0.527(2) 0.3864(16) 0.0414(14) 0.053(7) Uiso 1 1 d . . . . .
H3 H 0.486(2) 0.4637(17) 0.4230(14) 0.051(7) Uiso 1 1 d . . . . .
H23C H 0.476(2) 0.0462(17) 0.3060(13) 0.049(7) Uiso 1 1 d . . . . .
H1C H 0.2717(19) 0.8640(14) 0.0818(13) 0.037(6) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O2 1.4902(12) . ?
P1 O4 1.5003(11) . ?
P1 O3 1.5611(12) . ?
P1 O1 1.6160(12) . ?
P2 O6 1.4905(12) . ?
P2 O7 1.5002(11) . ?
P2 O8 1.5668(13) . ?
P2 O5 1.6024(11) . ?
O1 C1 1.4065(18) . ?
O3 H3 0.85(2) . ?
O5 C13 1.3943(18) . ?
O8 H8 0.75(2) . ?
N1 C4 1.465(2) . ?
N1 H1A 0.88(2) . ?
N1 H1B 0.90(2) . ?
N1 H1C 0.96(2) . ?
N2 C16 1.471(2) . ?
N2 H2A 0.86(2) . ?
N2 H2B 0.89(2) . ?
N2 H2C 0.96(2) . ?
C1 C6 1.396(2) . ?
C1 C2 1.397(2) . ?
C2 C3 1.391(2) . ?
C2 C7 1.525(2) . ?
C3 C4 1.382(2) . ?
C3 H3A 0.931(19) . ?
C4 C5 1.373(2) . ?
C5 C6 1.397(2) . ?
C5 H5 0.978(17) . ?
C6 C10 1.518(2) . ?
C7 C9 1.522(2) . ?
C7 C8 1.529(2) . ?
C7 H7 0.986(17) . ?
C8 H8A 0.98(2) . ?
C8 H8B 1.01(2) . ?
C8 H8C 0.99(2) . ?
C9 H9A 0.98(2) . ?
C9 H9B 0.97(2) . ?
C9 H9C 1.04(2) . ?
C10 C11 1.529(2) . ?
C10 C12 1.529(2) . ?
C10 H10 0.979(18) . ?
C11 H11A 1.01(2) . ?
C11 H11B 0.97(2) . ?
C11 H11C 1.00(2) . ?
C12 H12A 0.97(2) . ?
C12 H12B 1.01(2) . ?
C12 H12C 1.02(2) . ?
C13 C18 1.397(2) . ?
C13 C14 1.398(2) . ?
C14 C15 1.397(2) . ?
C14 C19 1.517(2) . ?
C15 C16 1.383(2) . ?
C15 H15 0.957(18) . ?
C16 C17 1.376(2) . ?
C17 C18 1.395(2) . ?
C17 H17 0.982(16) . ?
C18 C22 1.517(2) . ?
C19 C21 1.520(2) . ?
C19 C20 1.527(3) . ?
C19 H19 0.951(18) . ?
C20 H20A 0.97(2) . ?
C20 H20B 0.99(3) . ?
C20 H20C 1.01(3) . ?
C21 H21A 0.97(2) . ?
C21 H21B 1.00(2) . ?
C21 H21C 0.99(2) . ?
C22 C23 1.524(3) . ?
C22 C24 1.528(2) . ?
C22 H22 0.946(17) . ?
C23 H23A 0.99(2) . ?
C23 H23B 0.93(2) . ?
C23 H23C 0.94(2) . ?
C24 H24A 0.98(2) . ?
C24 H24B 0.99(2) . ?
C24 H24C 1.00(2) . ?
O9 H9D 0.90(3) . ?
O9 H9E 0.87(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
O2 P1 O4 117.78(6) . . ?
O2 P1 O3 107.71(7) . . ?
O4 P1 O3 110.88(6) . . ?
O2 P1 O1 110.87(6) . . ?
O4 P1 O1 103.52(6) . . ?
O3 P1 O1 105.41(6) . . ?
O6 P2 O7 117.66(6) . . ?
O6 P2 O8 107.28(7) . . ?
O7 P2 O8 109.87(7) . . ?
O6 P2 O5 111.02(6) . . ?
O7 P2 O5 105.47(6) . . ?
O8 P2 O5 104.82(7) . . ?
C1 O1 P1 127.11(10) . . ?
P1 O3 H3 114.2(17) . . ?
C13 O5 P2 129.56(10) . . ?
P2 O8 H8 116.3(19) . . ?
C4 N1 H1A 112.6(12) . . ?
C4 N1 H1B 110.5(12) . . ?
H1A N1 H1B 108.6(18) . . ?
C4 N1 H1C 112.6(12) . . ?
H1A N1 H1C 107.1(17) . . ?
H1B N1 H1C 105.2(16) . . ?
C16 N2 H2A 106.8(12) . . ?
C16 N2 H2B 113.4(12) . . ?
H2A N2 H2B 106.1(17) . . ?
C16 N2 H2C 113.8(11) . . ?
H2A N2 H2C 110.2(16) . . ?
H2B N2 H2C 106.2(16) . . ?
C6 C1 C2 123.41(14) . . ?
C6 C1 O1 119.01(14) . . ?
C2 C1 O1 117.12(13) . . ?
C3 C2 C1 117.12(14) . . ?
C3 C2 C7 121.28(15) . . ?
C1 C2 C7 121.55(14) . . ?
C4 C3 C2 120.06(15) . . ?
C4 C3 H3A 117.7(11) . . ?
C2 C3 H3A 122.2(11) . . ?
C5 C4 C3 121.85(15) . . ?
C5 C4 N1 118.64(14) . . ?
C3 C4 N1 119.51(15) . . ?
C4 C5 C6 120.18(14) . . ?
C4 C5 H5 120.1(10) . . ?
C6 C5 H5 119.8(10) . . ?
C1 C6 C5 116.97(15) . . ?
C1 C6 C10 122.63(14) . . ?
C5 C6 C10 120.37(14) . . ?
C9 C7 C2 111.46(14) . . ?
C9 C7 C8 110.25(15) . . ?
C2 C7 C8 112.39(14) . . ?
C9 C7 H7 108.7(10) . . ?
C2 C7 H7 106.6(10) . . ?
C8 C7 H7 107.2(10) . . ?
C7 C8 H8A 109.7(12) . . ?
C7 C8 H8B 110.7(12) . . ?
H8A C8 H8B 108.6(16) . . ?
C7 C8 H8C 110.6(12) . . ?
H8A C8 H8C 107.1(16) . . ?
H8B C8 H8C 110.1(16) . . ?
C7 C9 H9A 110.0(13) . . ?
C7 C9 H9B 111.4(12) . . ?
H9A C9 H9B 107.4(17) . . ?
C7 C9 H9C 109.8(11) . . ?
H9A C9 H9C 108.0(16) . . ?
H9B C9 H9C 110.2(16) . . ?
C6 C10 C11 111.38(14) . . ?
C6 C10 C12 111.33(14) . . ?
C11 C10 C12 111.26(14) . . ?
C6 C10 H10 107.0(10) . . ?
C11 C10 H10 107.9(10) . . ?
C12 C10 H10 107.8(10) . . ?
C10 C11 H11A 110.8(11) . . ?
C10 C11 H11B 110.2(12) . . ?
H11A C11 H11B 108.2(16) . . ?
C10 C11 H11C 113.5(11) . . ?
H11A C11 H11C 105.9(16) . . ?
H11B C11 H11C 108.0(17) . . ?
C10 C12 H12A 109.6(12) . . ?
C10 C12 H12B 113.5(11) . . ?
H12A C12 H12B 104.3(16) . . ?
C10 C12 H12C 111.4(11) . . ?
H12A C12 H12C 110.7(16) . . ?
H12B C12 H12C 107.2(16) . . ?
O5 C13 C18 118.70(14) . . ?
O5 C13 C14 118.09(13) . . ?
C18 C13 C14 122.86(14) . . ?
C15 C14 C13 117.76(14) . . ?
C15 C14 C19 122.05(14) . . ?
C13 C14 C19 120.08(14) . . ?
C16 C15 C14 119.94(15) . . ?
C16 C15 H15 119.0(10) . . ?
C14 C15 H15 121.0(10) . . ?
C17 C16 C15 121.40(14) . . ?
C17 C16 N2 118.40(14) . . ?
C15 C16 N2 120.18(14) . . ?
C16 C17 C18 120.66(14) . . ?
C16 C17 H17 118.0(10) . . ?
C18 C17 H17 121.4(10) . . ?
C17 C18 C13 117.36(14) . . ?
C17 C18 C22 120.88(13) . . ?
C13 C18 C22 121.75(14) . . ?
C14 C19 C21 113.40(14) . . ?
C14 C19 C20 109.88(14) . . ?
C21 C19 C20 111.37(17) . . ?
C14 C19 H19 105.9(10) . . ?
C21 C19 H19 108.7(10) . . ?
C20 C19 H19 107.2(10) . . ?
C19 C20 H20A 110.1(12) . . ?
C19 C20 H20B 108.3(13) . . ?
H20A C20 H20B 107.4(17) . . ?
C19 C20 H20C 111.4(13) . . ?
H20A C20 H20C 107.0(18) . . ?
H20B C20 H20C 112.5(19) . . ?
C19 C21 H21A 111.0(12) . . ?
C19 C21 H21B 110.2(12) . . ?
H21A C21 H21B 110.9(17) . . ?
C19 C21 H21C 109.6(12) . . ?
H21A C21 H21C 105.0(17) . . ?
H21B C21 H21C 110.1(16) . . ?
C18 C22 C23 109.31(14) . . ?
C18 C22 C24 113.09(15) . . ?
C23 C22 C24 110.83(16) . . ?
C18 C22 H22 105.9(10) . . ?
C23 C22 H22 110.9(11) . . ?
C24 C22 H22 106.7(10) . . ?
C22 C23 H23A 111.4(12) . . ?
C22 C23 H23B 108.7(13) . . ?
H23A C23 H23B 108.4(17) . . ?
C22 C23 H23C 111.5(14) . . ?
H23A C23 H23C 109.5(18) . . ?
H23B C23 H23C 107.3(18) . . ?
C22 C24 H24A 112.7(12) . . ?
C22 C24 H24B 109.7(12) . . ?
H24A C24 H24B 105.2(16) . . ?
C22 C24 H24C 109.8(12) . . ?
H24A C24 H24C 108.2(17) . . ?
H24B C24 H24C 111.2(17) . . ?
H9D O9 H9E 106(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
O2 P1 O1 C1 -17.04(14) . . . . ?
O4 P1 O1 C1 -144.24(12) . . . . ?
O3 P1 O1 C1 99.24(13) . . . . ?
O6 P2 O5 C13 -11.16(14) . . . . ?
O7 P2 O5 C13 -139.66(12) . . . . ?
O8 P2 O5 C13 104.36(13) . . . . ?
P1 O1 C1 C6 -88.48(16) . . . . ?
P1 O1 C1 C2 98.99(15) . . . . ?
C6 C1 C2 C3 7.1(2) . . . . ?
O1 C1 C2 C3 179.24(13) . . . . ?
C6 C1 C2 C7 -170.34(15) . . . . ?
O1 C1 C2 C7 1.8(2) . . . . ?
C1 C2 C3 C4 -2.1(2) . . . . ?
C7 C2 C3 C4 175.27(14) . . . . ?
C2 C3 C4 C5 -2.6(2) . . . . ?
C2 C3 C4 N1 178.05(14) . . . . ?
C3 C4 C5 C6 2.7(2) . . . . ?
N1 C4 C5 C6 -177.94(14) . . . . ?
C2 C1 C6 C5 -7.0(2) . . . . ?
O1 C1 C6 C5 -178.98(13) . . . . ?
C2 C1 C6 C10 170.96(14) . . . . ?
O1 C1 C6 C10 -1.1(2) . . . . ?
C4 C5 C6 C1 1.9(2) . . . . ?
C4 C5 C6 C10 -176.04(14) . . . . ?
C3 C2 C7 C9 88.70(19) . . . . ?
C1 C2 C7 C9 -94.00(19) . . . . ?
C3 C2 C7 C8 -35.7(2) . . . . ?
C1 C2 C7 C8 141.64(16) . . . . ?
C1 C6 C10 C11 -134.23(16) . . . . ?
C5 C6 C10 C11 43.6(2) . . . . ?
C1 C6 C10 C12 100.96(18) . . . . ?
C5 C6 C10 C12 -81.19(18) . . . . ?
P2 O5 C13 C18 -98.50(16) . . . . ?
P2 O5 C13 C14 88.02(17) . . . . ?
O5 C13 C14 C15 174.59(13) . . . . ?
C18 C13 C14 C15 1.4(2) . . . . ?
O5 C13 C14 C19 -1.6(2) . . . . ?
C18 C13 C14 C19 -174.82(14) . . . . ?
C13 C14 C15 C16 -1.8(2) . . . . ?
C19 C14 C15 C16 174.35(14) . . . . ?
C14 C15 C16 C17 1.5(2) . . . . ?
C14 C15 C16 N2 -177.17(14) . . . . ?
C15 C16 C17 C18 -0.7(2) . . . . ?
N2 C16 C17 C18 177.96(14) . . . . ?
C16 C17 C18 C13 0.3(2) . . . . ?
C16 C17 C18 C22 179.31(14) . . . . ?
O5 C13 C18 C17 -173.81(13) . . . . ?
C14 C13 C18 C17 -0.7(2) . . . . ?
O5 C13 C18 C22 7.2(2) . . . . ?
C14 C13 C18 C22 -179.66(15) . . . . ?
C15 C14 C19 C21 28.0(2) . . . . ?
C13 C14 C19 C21 -155.98(16) . . . . ?
C15 C14 C19 C20 -97.40(19) . . . . ?
C13 C14 C19 C20 78.7(2) . . . . ?
C17 C18 C22 C23 -87.38(18) . . . . ?
C13 C18 C22 C23 91.59(18) . . . . ?
C17 C18 C22 C24 36.6(2) . . . . ?
C13 C18 C22 C24 -144.43(16) . . . . ?

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
C17 H17 O4 0.982(16) 2.585(16) 3.2380(19) 124.0(12) 3_666
N1 H1A O2 0.88(2) 2.09(2) 2.936(2) 162.2(18) 2
N1 H1A O8 0.88(2) 2.52(2) 3.019(2) 117.2(15) 1_565
N2 H2A O4 0.86(2) 1.94(2) 2.7911(19) 169.5(17) 3_666
N1 H1B O7 0.90(2) 1.92(2) 2.7953(19) 162.4(18) 3_665
N2 H2B O6 0.89(2) 1.92(2) 2.771(2) 159.4(17) 2_655
N2 H2C O7 0.96(2) 1.81(2) 2.7598(19) 172.1(17) 4_666
O8 H8 O2 0.75(2) 1.90(3) 2.6007(18) 155(3) 2_545
O9 H9D O6 0.90(3) 1.87(3) 2.7403(19) 163(2) 4_566
O9 H9E O1 0.87(3) 1.99(3) 2.8504(18) 167(2) 3_666
O3 H3 O4 0.85(2) 1.75(2) 2.5997(17) 178(2) 3_666
N1 H1C O9 0.96(2) 1.76(2) 2.675(2) 159.3(18) 2
C17 H17 O4 0.982(16) 2.585(16) 3.2380(19) 124.0(12) 3_666
N1 H1A O2 0.88(2) 2.09(2) 2.936(2) 162.2(18) 2
N1 H1A O8 0.88(2) 2.52(2) 3.019(2) 117.2(15) 1_565
N2 H2A O4 0.86(2) 1.94(2) 2.7911(19) 169.5(17) 3_666
N1 H1B O7 0.90(2) 1.92(2) 2.7953(19) 162.4(18) 3_665
N2 H2B O6 0.89(2) 1.92(2) 2.771(2) 159.4(17) 2_655
N2 H2C O7 0.96(2) 1.81(2) 2.7598(19) 172.1(17) 4_666
O8 H8 O2 0.75(2) 1.90(3) 2.6007(18) 155(3) 2_545
O9 H9D O6 0.90(3) 1.87(3) 2.7403(19) 163(2) 4_566
O9 H9E O1 0.87(3) 1.99(3) 2.8504(18) 167(2) 3_666
O3 H3 O4 0.85(2) 1.75(2) 2.5997(17) 178(2) 3_666
N1 H1C O9 0.96(2) 1.76(2) 2.675(2) 159.3(18) 2

_refine_diff_density_max         0.219
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.043

