# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_mo_dd21111_0m
_database_code_depnum_ccdc_archive 'CCDC 2175608'
loop_
_audit_author_name
_audit_author_address
'Sun Jianting'
;Fudan University
China
;
_audit_update_record             
;
2022-05-29 deposited with the CCDC.	2022-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H24 N O4 P'
_chemical_formula_weight         313.32

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           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   10.2351(3)
_cell_length_b                   8.1643(2)
_cell_length_c                   20.5765(5)
_cell_angle_alpha                90
_cell_angle_beta                 98.1630(10)
_cell_angle_gamma                90
_cell_volume                     1702.00(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    213(2)
_cell_measurement_reflns_used    9610
_cell_measurement_theta_min      4.738
_cell_measurement_theta_max      54.930

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.223
_exptl_crystal_F_000             672
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.176
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6920
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      213(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26255
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.627
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             6651
_reflns_number_gt                6114
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.863
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    0.995

_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0887P)²+0.5003P] 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_abs_structure_details 
; 
 Flack x determined using 2587 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.20(3)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         6651
_refine_ls_number_parameters     425
_refine_ls_number_restraints     83
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0536
_refine_ls_wR_factor_ref         0.1477
_refine_ls_wR_factor_gt          0.1411
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.070
_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 0.28720(10) 0.58597(14) 0.78241(5) 0.0437(3) Uani 1 1 d . . . . .
O1 O 0.0982(3) 0.5378(5) 0.60119(16) 0.0716(11) Uani 1 1 d . . . . .
O2 O 0.4165(3) 0.5300(4) 0.81450(13) 0.0545(8) Uani 1 1 d . . . . .
O3 O 0.2210(3) 0.7265(4) 0.81738(14) 0.0543(8) Uani 1 1 d . . . . .
O4 O 0.1784(3) 0.4450(4) 0.77756(18) 0.0626(9) Uani 1 1 d D . . . .
N1 N 0.3062(3) 0.5429(4) 0.65504(14) 0.0406(8) Uani 1 1 d . . . . .
H1 H 0.3848 0.5002 0.6591 0.049 Uiso 1 1 calc R U . . .
C1 C 0.1581(4) 0.2844(7) 0.5181(2) 0.0591(12) Uani 1 1 d . . . . .
H1A H 0.0695 0.2941 0.5249 0.071 Uiso 1 1 calc R U . . .
C2 C 0.1902(5) 0.1823(7) 0.4697(2) 0.0660(14) Uani 1 1 d . . . . .
H2A H 0.1241 0.1205 0.4444 0.079 Uiso 1 1 calc R U . . .
C3 C 0.3186(5) 0.1709(7) 0.4583(2) 0.0629(13) Uani 1 1 d . . . . .
H3 H 0.3404 0.1033 0.4244 0.075 Uiso 1 1 calc R U . . .
C4 C 0.4152(4) 0.2580(7) 0.4964(2) 0.0619(14) Uani 1 1 d . . . . .
H4 H 0.5033 0.2494 0.4887 0.074 Uiso 1 1 calc R U . . .
C5 C 0.3838(4) 0.3586(6) 0.54591(18) 0.0475(10) Uani 1 1 d . . . . .
H5 H 0.4507 0.4174 0.5721 0.057 Uiso 1 1 calc R U . . .
C6 C 0.2540(4) 0.3728(5) 0.55699(17) 0.0420(9) Uani 1 1 d . . . . .
C7 C 0.2114(4) 0.4909(6) 0.60643(19) 0.0465(10) Uani 1 1 d . . . . .
C8 C 0.2760(4) 0.6705(5) 0.70037(18) 0.0422(9) Uani 1 1 d . . . . .
H8 H 0.1819 0.6984 0.6871 0.051 Uiso 1 1 calc R U . . .
C9 C 0.3525(5) 0.8287(6) 0.6946(2) 0.0574(11) Uani 1 1 d . . . . .
H9 H 0.3337 0.9026 0.7302 0.069 Uiso 1 1 calc R U . . .
C10 C 0.3011(8) 0.9114(9) 0.6293(3) 0.098(2) Uani 1 1 d . . . . .
H10A H 0.3213 0.8436 0.5934 0.146 Uiso 1 1 calc R U . . .
H10B H 0.3430 1.0175 0.6273 0.146 Uiso 1 1 calc R U . . .
H10C H 0.2063 0.9257 0.6259 0.146 Uiso 1 1 calc R U . . .
C11 C 0.5017(5) 0.8035(7) 0.7022(3) 0.0715(15) Uani 1 1 d . . . . .
H11A H 0.5327 0.7623 0.7459 0.107 Uiso 1 1 calc R U . . .
H11B H 0.5445 0.9071 0.6958 0.107 Uiso 1 1 calc R U . . .
H11C H 0.5227 0.7251 0.6698 0.107 Uiso 1 1 calc R U . . .
C12 C 0.1978(7) 0.7093(8) 0.8850(2) 0.0775(16) Uani 1 1 d D . . . .
H12A H 0.1305 0.6251 0.8876 0.093 Uiso 1 1 calc R U . . .
H12B H 0.2794 0.6733 0.9121 0.093 Uiso 1 1 calc R U . . .
C13 C 0.1557(9) 0.8580(11) 0.9100(3) 0.115(3) Uani 1 1 d D . . . .
H13A H 0.0748 0.8936 0.8834 0.172 Uiso 1 1 calc R U . . .
H13B H 0.2234 0.9407 0.9088 0.172 Uiso 1 1 calc R U . . .
H13C H 0.1400 0.8422 0.9550 0.172 Uiso 1 1 calc R U . . .
C14 C 0.2178(8) 0.2719(10) 0.7690(5) 0.070(2) Uani 0.7 1 d D U P A 1
H14A H 0.2518 0.2586 0.7272 0.084 Uiso 0.7 1 calc R U P A 1
H14B H 0.2871 0.2399 0.8046 0.084 Uiso 0.7 1 calc R U P A 1
C15 C 0.1016(11) 0.1703(13) 0.7701(6) 0.077(2) Uani 0.6 1 d D U P A 1
H15A H 0.0720 0.1791 0.8127 0.116 Uiso 0.6 1 calc R U P A 1
H15B H 0.1233 0.0572 0.7621 0.116 Uiso 0.6 1 calc R U P A 1
H15C H 0.0319 0.2069 0.7363 0.116 Uiso 0.6 1 calc R U P A 1
C14' C 0.185(2) 0.285(2) 0.7931(11) 0.078(3) Uani 0.3 1 d D U P A 2
H14C H 0.1398 0.2654 0.8311 0.093 Uiso 0.3 1 calc R U P A 2
H14D H 0.2779 0.2530 0.8047 0.093 Uiso 0.3 1 calc R U P A 2
C15' C 0.1216(18) 0.185(2) 0.7350(9) 0.083(3) Uani 0.4 1 d D U P A 2
H15D H 0.0266 0.1987 0.7299 0.124 Uiso 0.4 1 calc R U P A 2
H15E H 0.1431 0.0699 0.7427 0.124 Uiso 0.4 1 calc R U P A 2
H15F H 0.1544 0.2209 0.6954 0.124 Uiso 0.4 1 calc R U P A 2
P2 P 0.68382(10) 0.34859(15) 0.71786(5) 0.0486(3) Uani 1 1 d . . . . .
O5 O 0.9085(3) 0.4678(5) 0.89339(15) 0.0597(9) Uani 1 1 d . . . . .
O6 O 0.5424(3) 0.3457(5) 0.69274(14) 0.0611(9) Uani 1 1 d . . . . .
O7 O 0.7390(3) 0.5215(5) 0.70510(15) 0.0611(9) Uani 1 1 d . . . . .
O8 O 0.7686(3) 0.2185(5) 0.68583(15) 0.0657(10) Uani 1 1 d D . . . .
N2 N 0.6984(3) 0.4334(4) 0.84530(14) 0.0367(7) Uani 1 1 d . . . . .
H2 H 0.6173 0.4684 0.8410 0.044 Uiso 1 1 calc R U . . .
C16 C 0.6130(4) 0.6448(6) 0.9445(2) 0.0549(11) Uani 1 1 d . . . . .
H16 H 0.5467 0.5962 0.9144 0.066 Uiso 1 1 calc R U . . .
C17 C 0.5792(5) 0.7447(8) 0.9939(3) 0.0736(17) Uani 1 1 d . . . . .
H17 H 0.4898 0.7626 0.9973 0.088 Uiso 1 1 calc R U . . .
C18 C 0.6755(5) 0.8182(7) 1.0380(2) 0.0669(14) Uani 1 1 d . . . . .
H18 H 0.6516 0.8860 1.0713 0.080 Uiso 1 1 calc R U . . .
C19 C 0.8055(5) 0.7922(6) 1.0332(2) 0.0583(12) Uani 1 1 d . . . . .
H19 H 0.8712 0.8428 1.0631 0.070 Uiso 1 1 calc R U . . .
C20 C 0.8412(4) 0.6918(6) 0.9844(2) 0.0474(9) Uani 1 1 d . . . . .
H20 H 0.9310 0.6742 0.9815 0.057 Uiso 1 1 calc R U . . .
C21 C 0.7445(4) 0.6164(5) 0.93966(17) 0.0384(8) Uani 1 1 d . . . . .
C22 C 0.7904(4) 0.5015(5) 0.89059(18) 0.0401(8) Uani 1 1 d . . . . .
C23 C 0.7341(4) 0.3012(5) 0.80349(17) 0.0384(8) Uani 1 1 d . . . . .
H23 H 0.8318 0.2993 0.8096 0.046 Uiso 1 1 calc R U . . .
C24 C 0.6918(5) 0.1304(6) 0.8243(2) 0.0576(11) Uani 1 1 d . . . . .
H24 H 0.7130 0.0509 0.7910 0.069 Uiso 1 1 calc R U . . .
C25 C 0.5452(5) 0.1172(7) 0.8280(3) 0.0711(14) Uani 1 1 d . . . . .
H25A H 0.5231 0.1862 0.8633 0.107 Uiso 1 1 calc R U . . .
H25B H 0.5231 0.0043 0.8364 0.107 Uiso 1 1 calc R U . . .
H25C H 0.4955 0.1526 0.7867 0.107 Uiso 1 1 calc R U . . .
C26 C 0.7729(7) 0.0836(8) 0.8901(3) 0.0843(17) Uani 1 1 d . . . . .
H26A H 0.8662 0.0924 0.8868 0.126 Uiso 1 1 calc R U . . .
H26B H 0.7526 -0.0282 0.9011 0.126 Uiso 1 1 calc R U . . .
H26C H 0.7513 0.1569 0.9241 0.126 Uiso 1 1 calc R U . . .
C27 C 0.8741(5) 0.5674(8) 0.7214(3) 0.0664(13) Uani 1 1 d D . . . .
H27A H 0.9232 0.5368 0.6857 0.080 Uiso 1 1 calc R U . . .
H27B H 0.9133 0.5102 0.7613 0.080 Uiso 1 1 calc R U . . .
C28 C 0.8819(7) 0.7473(10) 0.7321(5) 0.110(3) Uani 1 1 d D . . . .
H28A H 0.8336 0.8028 0.6945 0.165 Uiso 1 1 calc R U . . .
H28B H 0.9736 0.7815 0.7376 0.165 Uiso 1 1 calc R U . . .
H28C H 0.8436 0.7750 0.7712 0.165 Uiso 1 1 calc R U . . .
C29 C 0.7339(8) 0.1566(12) 0.6190(3) 0.0684(19) Uani 0.7 1 d D U P B 1
H29A H 0.7282 0.0368 0.6196 0.082 Uiso 0.7 1 calc R U P B 1
H29B H 0.6479 0.2001 0.5997 0.082 Uiso 0.7 1 calc R U P B 1
C30 C 0.8322(16) 0.206(2) 0.5812(7) 0.091(3) Uani 0.5 1 d D U P B 1
H30A H 0.8189 0.3204 0.5690 0.136 Uiso 0.5 1 calc R U P B 1
H30B H 0.8262 0.1396 0.5419 0.136 Uiso 0.5 1 calc R U P B 1
H30C H 0.9186 0.1926 0.6068 0.136 Uiso 0.5 1 calc R U P B 1
C29' C 0.780(2) 0.251(3) 0.6132(8) 0.076(3) Uani 0.3 1 d D U P B 2
H29C H 0.6925 0.2533 0.5867 0.091 Uiso 0.3 1 calc R U P B 2
H29D H 0.8246 0.3550 0.6080 0.091 Uiso 0.3 1 calc R U P B 2
C30' C 0.8570(16) 0.1149(19) 0.5939(7) 0.086(3) Uani 0.5 1 d D U P B 2
H30D H 0.9492 0.1463 0.5982 0.129 Uiso 0.5 1 calc R U P B 2
H30E H 0.8260 0.0859 0.5486 0.129 Uiso 0.5 1 calc R U P B 2
H30F H 0.8475 0.0215 0.6220 0.129 Uiso 0.5 1 calc R U P B 2


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O2 1.466(3) . ?
P1 O3 1.559(3) . ?
P1 O4 1.595(4) . ?
P1 C8 1.812(4) . ?
O1 C7 1.210(5) . ?
O3 C12 1.452(6) . ?
O4 C14' 1.34(2) . ?
O4 C14 1.487(9) . ?
N1 C7 1.359(5) . ?
N1 C8 1.461(5) . ?
N1 H1 0.8700 . ?
C1 C2 1.374(7) . ?
C1 C6 1.378(6) . ?
C1 H1A 0.9400 . ?
C2 C3 1.371(7) . ?
C2 H2A 0.9400 . ?
C3 C4 1.370(6) . ?
C3 H3 0.9400 . ?
C4 C5 1.382(6) . ?
C4 H4 0.9400 . ?
C5 C6 1.385(5) . ?
C5 H5 0.9400 . ?
C6 C7 1.510(6) . ?
C8 C9 1.524(6) . ?
C8 H8 0.9900 . ?
C9 C11 1.526(7) . ?
C9 C10 1.528(8) . ?
C9 H9 0.9900 . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 H10C 0.9700 . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 H11C 0.9700 . ?
C12 C13 1.410(9) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?
C14 C15 1.452(13) . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 H15C 0.9700 . ?
C14' C15' 1.52(2) . ?
C14' H14C 0.9800 . ?
C14' H14D 0.9800 . ?
C15' H15D 0.9700 . ?
C15' H15E 0.9700 . ?
C15' H15F 0.9700 . ?
P2 O6 1.466(3) . ?
P2 O7 1.557(4) . ?
P2 O8 1.574(3) . ?
P2 C23 1.806(4) . ?
O5 C22 1.233(5) . ?
O7 C27 1.425(6) . ?
O8 C29 1.460(7) . ?
O8 C29' 1.538(17) . ?
N2 C22 1.347(5) . ?
N2 C23 1.458(5) . ?
N2 H2 0.8700 . ?
C16 C21 1.383(5) . ?
C16 C17 1.383(6) . ?
C16 H16 0.9400 . ?
C17 C18 1.378(7) . ?
C17 H17 0.9400 . ?
C18 C19 1.365(7) . ?
C18 H18 0.9400 . ?
C19 C20 1.384(6) . ?
C19 H19 0.9400 . ?
C20 C21 1.396(5) . ?
C20 H20 0.9400 . ?
C21 C22 1.502(5) . ?
C23 C24 1.538(6) . ?
C23 H23 0.9900 . ?
C24 C25 1.518(7) . ?
C24 C26 1.534(7) . ?
C24 H24 0.9900 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 H25C 0.9700 . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26 H26C 0.9700 . ?
C27 C28 1.485(10) . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C28 H28C 0.9700 . ?
C29 C30 1.415(15) . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C30 H30A 0.9700 . ?
C30 H30B 0.9700 . ?
C30 H30C 0.9700 . ?
C29' C30' 1.448(18) . ?
C29' H29C 0.9800 . ?
C29' H29D 0.9800 . ?
C30' H30D 0.9700 . ?
C30' H30E 0.9700 . ?
C30' H30F 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 P1 O3 116.45(18) . . ?
O2 P1 O4 112.4(2) . . ?
O3 P1 O4 102.38(18) . . ?
O2 P1 C8 118.16(18) . . ?
O3 P1 C8 100.11(17) . . ?
O4 P1 C8 105.38(19) . . ?
C12 O3 P1 120.8(3) . . ?
C14' O4 P1 132.3(11) . . ?
C14 O4 P1 119.6(4) . . ?
C7 N1 C8 119.9(3) . . ?
C7 N1 H1 120.0 . . ?
C8 N1 H1 120.0 . . ?
C2 C1 C6 121.0(4) . . ?
C2 C1 H1A 119.5 . . ?
C6 C1 H1A 119.5 . . ?
C3 C2 C1 119.9(4) . . ?
C3 C2 H2A 120.0 . . ?
C1 C2 H2A 120.0 . . ?
C4 C3 C2 119.9(4) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.4(4) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C6 120.0(4) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 118.8(4) . . ?
C1 C6 C7 118.4(4) . . ?
C5 C6 C7 122.7(4) . . ?
O1 C7 N1 122.8(4) . . ?
O1 C7 C6 120.4(4) . . ?
N1 C7 C6 116.8(3) . . ?
N1 C8 C9 113.4(3) . . ?
N1 C8 P1 109.4(3) . . ?
C9 C8 P1 115.5(3) . . ?
N1 C8 H8 105.9 . . ?
C9 C8 H8 105.9 . . ?
P1 C8 H8 105.9 . . ?
C8 C9 C11 113.3(4) . . ?
C8 C9 C10 109.1(5) . . ?
C11 C9 C10 111.4(5) . . ?
C8 C9 H9 107.6 . . ?
C11 C9 H9 107.6 . . ?
C10 C9 H9 107.6 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 O3 111.5(6) . . ?
C13 C12 H12A 109.3 . . ?
O3 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
O3 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 O4 107.7(7) . . ?
C15 C14 H14A 110.2 . . ?
O4 C14 H14A 110.2 . . ?
C15 C14 H14B 110.2 . . ?
O4 C14 H14B 110.2 . . ?
H14A C14 H14B 108.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C14' C15' 109.7(17) . . ?
O4 C14' H14C 109.7 . . ?
C15' C14' H14C 109.7 . . ?
O4 C14' H14D 109.7 . . ?
C15' C14' H14D 109.7 . . ?
H14C C14' H14D 108.2 . . ?
C14' C15' H15D 109.5 . . ?
C14' C15' H15E 109.5 . . ?
H15D C15' H15E 109.5 . . ?
C14' C15' H15F 109.5 . . ?
H15D C15' H15F 109.5 . . ?
H15E C15' H15F 109.5 . . ?
O6 P2 O7 108.6(2) . . ?
O6 P2 O8 114.64(19) . . ?
O7 P2 O8 107.8(2) . . ?
O6 P2 C23 118.07(19) . . ?
O7 P2 C23 107.38(19) . . ?
O8 P2 C23 99.57(17) . . ?
C27 O7 P2 124.2(3) . . ?
C29 O8 P2 123.5(4) . . ?
C29' O8 P2 114.5(7) . . ?
C22 N2 C23 120.3(3) . . ?
C22 N2 H2 119.8 . . ?
C23 N2 H2 119.8 . . ?
C21 C16 C17 119.9(4) . . ?
C21 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C18 C17 C16 120.7(4) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C19 C18 C17 119.9(4) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 120.3(4) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 H19 119.8 . . ?
C19 C20 C21 120.3(4) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C16 C21 C20 119.0(4) . . ?
C16 C21 C22 123.6(3) . . ?
C20 C21 C22 117.3(3) . . ?
O5 C22 N2 121.6(4) . . ?
O5 C22 C21 120.4(3) . . ?
N2 C22 C21 117.9(3) . . ?
N2 C23 C24 113.8(3) . . ?
N2 C23 P2 110.9(2) . . ?
C24 C23 P2 114.4(3) . . ?
N2 C23 H23 105.6 . . ?
C24 C23 H23 105.6 . . ?
P2 C23 H23 105.6 . . ?
C25 C24 C26 110.6(5) . . ?
C25 C24 C23 113.4(4) . . ?
C26 C24 C23 109.4(4) . . ?
C25 C24 H24 107.7 . . ?
C26 C24 H24 107.7 . . ?
C23 C24 H24 107.7 . . ?
C24 C25 H25A 109.5 . . ?
C24 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C24 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C24 C26 H26A 109.5 . . ?
C24 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C24 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
O7 C27 C28 109.0(5) . . ?
O7 C27 H27A 109.9 . . ?
C28 C27 H27A 109.9 . . ?
O7 C27 H27B 109.9 . . ?
C28 C27 H27B 109.9 . . ?
H27A C27 H27B 108.3 . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C30 C29 O8 108.8(9) . . ?
C30 C29 H29A 109.9 . . ?
O8 C29 H29A 109.9 . . ?
C30 C29 H29B 109.9 . . ?
O8 C29 H29B 109.9 . . ?
H29A C29 H29B 108.3 . . ?
C29 C30 H30A 109.5 . . ?
C29 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C29 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C30' C29' O8 104.8(13) . . ?
C30' C29' H29C 110.8 . . ?
O8 C29' H29C 110.8 . . ?
C30' C29' H29D 110.8 . . ?
O8 C29' H29D 110.8 . . ?
H29C C29' H29D 108.9 . . ?
C29' C30' H30D 109.5 . . ?
C29' C30' H30E 109.5 . . ?
H30D C30' H30E 109.5 . . ?
C29' C30' H30F 109.5 . . ?
H30D C30' H30F 109.5 . . ?
H30E C30' H30F 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
O2 P1 O3 C12 -56.0(5) . . . . ?
O4 P1 O3 C12 67.0(4) . . . . ?
C8 P1 O3 C12 175.4(4) . . . . ?
O2 P1 O4 C14' -5.2(14) . . . . ?
O3 P1 O4 C14' -130.9(14) . . . . ?
C8 P1 O4 C14' 124.8(14) . . . . ?
O2 P1 O4 C14 -32.9(6) . . . . ?
O3 P1 O4 C14 -158.6(6) . . . . ?
C8 P1 O4 C14 97.1(6) . . . . ?
C6 C1 C2 C3 -1.8(9) . . . . ?
C1 C2 C3 C4 1.7(9) . . . . ?
C2 C3 C4 C5 -0.5(9) . . . . ?
C3 C4 C5 C6 -0.5(8) . . . . ?
C2 C1 C6 C5 0.8(8) . . . . ?
C2 C1 C6 C7 176.1(5) . . . . ?
C4 C5 C6 C1 0.4(7) . . . . ?
C4 C5 C6 C7 -174.8(4) . . . . ?
C8 N1 C7 O1 -5.2(7) . . . . ?
C8 N1 C7 C6 173.3(4) . . . . ?
C1 C6 C7 O1 -18.4(7) . . . . ?
C5 C6 C7 O1 156.8(5) . . . . ?
C1 C6 C7 N1 163.1(4) . . . . ?
C5 C6 C7 N1 -21.7(6) . . . . ?
C7 N1 C8 C9 -114.5(4) . . . . ?
C7 N1 C8 P1 115.0(4) . . . . ?
O2 P1 C8 N1 65.0(3) . . . . ?
O3 P1 C8 N1 -167.5(3) . . . . ?
O4 P1 C8 N1 -61.5(3) . . . . ?
O2 P1 C8 C9 -64.3(3) . . . . ?
O3 P1 C8 C9 63.1(3) . . . . ?
O4 P1 C8 C9 169.1(3) . . . . ?
N1 C8 C9 C11 -54.8(5) . . . . ?
P1 C8 C9 C11 72.6(4) . . . . ?
N1 C8 C9 C10 69.9(5) . . . . ?
P1 C8 C9 C10 -162.7(4) . . . . ?
P1 O3 C12 C13 171.2(5) . . . . ?
C14' O4 C14 C15 49(2) . . . . ?
P1 O4 C14 C15 176.6(7) . . . . ?
C14 O4 C14' C15' -59(2) . . . . ?
P1 O4 C14' C15' -128.3(14) . . . . ?
O6 P2 O7 C27 -178.1(4) . . . . ?
O8 P2 O7 C27 -53.4(4) . . . . ?
C23 P2 O7 C27 53.1(4) . . . . ?
O6 P2 O8 C29 28.8(6) . . . . ?
O7 P2 O8 C29 -92.3(6) . . . . ?
C23 P2 O8 C29 155.8(6) . . . . ?
O6 P2 O8 C29' 68.3(12) . . . . ?
O7 P2 O8 C29' -52.8(12) . . . . ?
C23 P2 O8 C29' -164.6(12) . . . . ?
C21 C16 C17 C18 0.7(9) . . . . ?
C16 C17 C18 C19 -0.1(10) . . . . ?
C17 C18 C19 C20 -0.3(9) . . . . ?
C18 C19 C20 C21 0.1(8) . . . . ?
C17 C16 C21 C20 -0.9(7) . . . . ?
C17 C16 C21 C22 175.9(5) . . . . ?
C19 C20 C21 C16 0.5(7) . . . . ?
C19 C20 C21 C22 -176.6(4) . . . . ?
C23 N2 C22 O5 8.0(6) . . . . ?
C23 N2 C22 C21 -169.9(3) . . . . ?
C16 C21 C22 O5 -172.0(4) . . . . ?
C20 C21 C22 O5 4.9(6) . . . . ?
C16 C21 C22 N2 5.9(6) . . . . ?
C20 C21 C22 N2 -177.2(4) . . . . ?
C22 N2 C23 C24 102.8(4) . . . . ?
C22 N2 C23 P2 -126.6(3) . . . . ?
O6 P2 C23 N2 -71.2(3) . . . . ?
O7 P2 C23 N2 51.8(3) . . . . ?
O8 P2 C23 N2 164.1(3) . . . . ?
O6 P2 C23 C24 59.0(3) . . . . ?
O7 P2 C23 C24 -177.9(3) . . . . ?
O8 P2 C23 C24 -65.7(3) . . . . ?
N2 C23 C24 C25 56.0(5) . . . . ?
P2 C23 C24 C25 -72.9(4) . . . . ?
N2 C23 C24 C26 -68.1(5) . . . . ?
P2 C23 C24 C26 163.0(4) . . . . ?
P2 O7 C27 C28 -153.9(5) . . . . ?
C29' O8 C29 C30 29.5(15) . . . . ?
P2 O8 C29 C30 115.2(9) . . . . ?
C29 O8 C29' C30' -64.0(14) . . . . ?
P2 O8 C29' C30' -178.1(11) . . . . ?

_refine_diff_density_max         0.579
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.047

_shelxl_version_number           2013-4

####################################################################### 
# 
# 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_mo_dd21153_0m
_database_code_depnum_ccdc_archive 'CCDC 2175609'
loop_
_audit_author_name
_audit_author_address
'Jian-Ting Sun'
;Fudan University
China
;
_audit_update_record             
;
2022-05-29 deposited with the CCDC.	2022-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H25 F N O5 P'
_chemical_formula_weight         373.35

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'

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

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

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

_cell_length_a                   9.2680(4)
_cell_length_b                   9.7857(5)
_cell_length_c                   11.9313(6)
_cell_angle_alpha                76.990(2)
_cell_angle_beta                 68.2280(10)
_cell_angle_gamma                77.696(2)
_cell_volume                     969.02(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5088
_cell_measurement_theta_min      4.316
_cell_measurement_theta_max      48.154

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.280
_exptl_crystal_F_000             396
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.176
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4652
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16343
_diffrn_reflns_av_unetI/netI     0.0539
_diffrn_reflns_av_R_equivalents  0.0667
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.483
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3793
_reflns_number_gt                2586
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0523P)²+0.3610P] 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     SHELXL
_refine_ls_extinction_coef       0.050(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3793
_refine_ls_number_parameters     270
_refine_ls_number_restraints     83
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1493
_refine_ls_wR_factor_gt          0.1272
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.029
_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 0.53745(8) 0.31857(8) 0.34474(6) 0.0650(3) Uani 1 1 d . . . . .
F1 F -0.1045(3) 0.2879(3) 0.85697(16) 0.1348(9) Uani 1 1 d . . . . .
O1 O 0.6437(2) 0.4188(2) 0.3196(2) 0.1029(8) Uani 1 1 d . . . . .
O2 O 0.5879(2) 0.2127(2) 0.2538(2) 0.0951(7) Uani 1 1 d D . . . .
O3 O 0.5047(2) 0.2189(2) 0.47099(19) 0.0936(7) Uani 1 1 d D . . . .
O4 O 0.1122(2) 0.1802(2) 0.29901(18) 0.0868(6) Uani 1 1 d . . . . .
O5 O 0.2985(2) 0.3132(2) 0.17004(15) 0.0703(5) Uani 1 1 d . . . . .
N1 N 0.2350(2) 0.3011(2) 0.36976(17) 0.0549(5) Uani 1 1 d . . . . .
C1 C 0.1381(3) 0.2824(2) 0.4951(2) 0.0556(6) Uani 1 1 d . . . . .
C2 C 0.0415(3) 0.1802(3) 0.5587(2) 0.0683(7) Uani 1 1 d . . . . .
H2 H 0.0314 0.1114 0.5206 0.082 Uiso 1 1 calc R U . . .
C3 C -0.0402(3) 0.1849(3) 0.6828(3) 0.0819(9) Uani 1 1 d . . . . .
H3 H -0.1067 0.1185 0.7293 0.098 Uiso 1 1 calc R U . . .
C4 C -0.0220(4) 0.2864(4) 0.7349(3) 0.0873(9) Uani 1 1 d . . . . .
C5 C 0.0734(3) 0.3885(3) 0.6736(2) 0.0778(8) Uani 1 1 d . . . . .
H5 H 0.0828 0.4567 0.7127 0.093 Uiso 1 1 calc R U . . .
C6 C 0.1546(3) 0.3849(3) 0.5509(2) 0.0584(6) Uani 1 1 d . . . . .
C7 C 0.2637(3) 0.4823(3) 0.4607(2) 0.0609(6) Uani 1 1 d . . . . .
H7A H 0.3410 0.4960 0.4925 0.073 Uiso 1 1 calc R U . . .
H7B H 0.2067 0.5737 0.4392 0.073 Uiso 1 1 calc R U . . .
C8 C 0.3415(3) 0.4033(2) 0.3500(2) 0.0548(6) Uani 1 1 d . . . . .
H8 H 0.3468 0.4701 0.2743 0.066 Uiso 1 1 calc R U . . .
C9 C 0.7214(6) 0.2041(6) 0.1473(4) 0.1073(15) Uani 0.7 1 d D U P A 1
H9A H 0.7756 0.2849 0.1305 0.129 Uiso 0.7 1 calc R U P A 1
H9B H 0.6890 0.2068 0.0782 0.129 Uiso 0.7 1 calc R U P A 1
C10 C 0.8272(11) 0.0740(11) 0.1623(8) 0.116(2) Uani 0.6 1 d D U P A 1
H10A H 0.8713 0.0776 0.2225 0.174 Uiso 0.6 1 calc R U P A 1
H10B H 0.9100 0.0637 0.0857 0.174 Uiso 0.6 1 calc R U P A 1
H10C H 0.7703 -0.0053 0.1884 0.174 Uiso 0.6 1 calc R U P A 1
C11 C 0.6252(5) 0.1486(5) 0.5198(4) 0.1068(13) Uani 0.8 1 d D U P B 1
H11A H 0.7184 0.1949 0.4825 0.128 Uiso 0.8 1 calc R U P B 1
H11B H 0.6530 0.0499 0.5090 0.128 Uiso 0.8 1 calc R U P B 1
C12 C 0.5453(12) 0.1633(11) 0.6568(9) 0.118(2) Uani 0.5 1 d D U P B 1
H12A H 0.5212 0.2618 0.6647 0.177 Uiso 0.5 1 calc R U P B 1
H12B H 0.6150 0.1156 0.7007 0.177 Uiso 0.5 1 calc R U P B 1
H12C H 0.4501 0.1217 0.6899 0.177 Uiso 0.5 1 calc R U P B 1
C9' C 0.7494(13) 0.1373(15) 0.2368(11) 0.111(2) Uani 0.3 1 d D U P A 2
H9'1 H 0.7504 0.0597 0.3035 0.133 Uiso 0.3 1 calc R U P A 2
H9'2 H 0.8188 0.2014 0.2324 0.133 Uiso 0.3 1 calc R U P A 2
C10' C 0.7983(18) 0.0832(17) 0.1180(10) 0.107(3) Uani 0.4 1 d D U P A 2
H10D H 0.8703 -0.0031 0.1199 0.161 Uiso 0.4 1 calc R U P A 2
H10E H 0.8485 0.1527 0.0520 0.161 Uiso 0.4 1 calc R U P A 2
H10F H 0.7074 0.0654 0.1062 0.161 Uiso 0.4 1 calc R U P A 2
C11' C 0.493(2) 0.2233(19) 0.5933(14) 0.109(3) Uani 0.2 1 d D U P B 2
H11C H 0.3860 0.2144 0.6478 0.131 Uiso 0.2 1 calc R U P B 2
H11D H 0.5167 0.3135 0.5969 0.131 Uiso 0.2 1 calc R U P B 2
C12' C 0.6035(11) 0.1057(10) 0.6333(9) 0.110(2) Uani 0.5 1 d D U P B 2
H12D H 0.5583 0.0194 0.6590 0.165 Uiso 0.5 1 calc R U P B 2
H12E H 0.6234 0.1279 0.7002 0.165 Uiso 0.5 1 calc R U P B 2
H12F H 0.7004 0.0941 0.5664 0.165 Uiso 0.5 1 calc R U P B 2
C13 C 0.2065(3) 0.2581(3) 0.2794(2) 0.0612(6) Uani 1 1 d . . . . .
C14 C 0.2876(3) 0.2873(3) 0.0575(2) 0.0713(7) Uani 1 1 d D . . . .
C15 C 0.1299(5) 0.3567(5) 0.0492(4) 0.1237(14) Uani 1 1 d D . . . .
H15A H 0.0492 0.3082 0.1120 0.186 Uiso 1 1 calc R U . . .
H15B H 0.1269 0.3524 -0.0295 0.186 Uiso 1 1 calc R U . . .
H15C H 0.1129 0.4540 0.0597 0.186 Uiso 1 1 calc R U . . .
C16 C 0.3197(6) 0.1320(4) 0.0523(3) 0.1238(14) Uani 1 1 d D . . . .
H16A H 0.4103 0.0903 0.0753 0.186 Uiso 1 1 calc R U . . .
H16B H 0.3388 0.1181 -0.0294 0.186 Uiso 1 1 calc R U . . .
H16C H 0.2306 0.0881 0.1076 0.186 Uiso 1 1 calc R U . . .
C17 C 0.4163(5) 0.3630(5) -0.0416(3) 0.1208(14) Uani 1 1 d D . . . .
H17A H 0.4009 0.4599 -0.0306 0.181 Uiso 1 1 calc R U . . .
H17B H 0.4128 0.3598 -0.1204 0.181 Uiso 1 1 calc R U . . .
H17C H 0.5166 0.3171 -0.0364 0.181 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.443(2) . ?
P1 O2 1.547(2) . ?
P1 O3 1.561(2) . ?
P1 C8 1.813(2) . ?
F1 C4 1.373(3) . ?
O2 C9 1.410(5) . ?
O2 C9' 1.482(11) . ?
O3 C11 1.426(4) . ?
O3 C11' 1.431(14) . ?
O4 C13 1.206(3) . ?
O5 C13 1.332(3) . ?
O5 C14 1.464(3) . ?
N1 C13 1.368(3) . ?
N1 C1 1.423(3) . ?
N1 C8 1.474(3) . ?
C1 C6 1.384(3) . ?
C1 C2 1.384(3) . ?
C2 C3 1.396(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.352(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.372(4) . ?
C5 C6 1.380(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.493(3) . ?
C7 C8 1.542(3) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8 0.9800 . ?
C9 C10 1.453(9) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 C12 1.550(10) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C9' C10' 1.502(13) . ?
C9' H9'1 0.9700 . ?
C9' H9'2 0.9700 . ?
C10' H10D 0.9600 . ?
C10' H10E 0.9600 . ?
C10' H10F 0.9600 . ?
C11' C12' 1.491(14) . ?
C11' H11C 0.9700 . ?
C11' H11D 0.9700 . ?
C12' H12D 0.9600 . ?
C12' H12E 0.9600 . ?
C12' H12F 0.9600 . ?
C14 C16 1.496(4) . ?
C14 C15 1.504(4) . ?
C14 C17 1.519(4) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 O2 115.67(13) . . ?
O1 P1 O3 116.18(13) . . ?
O2 P1 O3 102.57(14) . . ?
O1 P1 C8 112.87(12) . . ?
O2 P1 C8 105.90(11) . . ?
O3 P1 C8 102.11(11) . . ?
C9 O2 P1 128.6(3) . . ?
C9' O2 P1 112.3(5) . . ?
C11 O3 P1 123.2(2) . . ?
C11' O3 P1 138.7(8) . . ?
C13 O5 C14 121.1(2) . . ?
C13 N1 C1 124.1(2) . . ?
C13 N1 C8 125.3(2) . . ?
C1 N1 C8 108.91(18) . . ?
C6 C1 C2 122.0(2) . . ?
C6 C1 N1 109.3(2) . . ?
C2 C1 N1 128.7(2) . . ?
C1 C2 C3 117.1(3) . . ?
C1 C2 H2 121.5 . . ?
C3 C2 H2 121.5 . . ?
C4 C3 C2 119.7(3) . . ?
C4 C3 H3 120.2 . . ?
C2 C3 H3 120.2 . . ?
C3 C4 C5 124.2(3) . . ?
C3 C4 F1 118.1(3) . . ?
C5 C4 F1 117.7(3) . . ?
C4 C5 C6 116.6(3) . . ?
C4 C5 H5 121.7 . . ?
C6 C5 H5 121.7 . . ?
C5 C6 C1 120.5(2) . . ?
C5 C6 C7 128.9(2) . . ?
C1 C6 C7 110.7(2) . . ?
C6 C7 C8 102.94(19) . . ?
C6 C7 H7A 111.2 . . ?
C8 C7 H7A 111.2 . . ?
C6 C7 H7B 111.2 . . ?
C8 C7 H7B 111.2 . . ?
H7A C7 H7B 109.1 . . ?
N1 C8 C7 104.28(18) . . ?
N1 C8 P1 112.87(16) . . ?
C7 C8 P1 110.04(16) . . ?
N1 C8 H8 109.8 . . ?
C7 C8 H8 109.8 . . ?
P1 C8 H8 109.8 . . ?
O2 C9 C10 110.6(5) . . ?
O2 C9 H9A 109.5 . . ?
C10 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
C10 C9 H9B 109.5 . . ?
H9A C9 H9B 108.1 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O3 C11 C12 101.8(5) . . ?
O3 C11 H11A 111.4 . . ?
C12 C11 H11A 111.4 . . ?
O3 C11 H11B 111.4 . . ?
C12 C11 H11B 111.4 . . ?
H11A C11 H11B 109.3 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O2 C9' C10' 104.4(10) . . ?
O2 C9' H9'1 110.9 . . ?
C10' C9' H9'1 110.9 . . ?
O2 C9' H9'2 110.9 . . ?
C10' C9' H9'2 110.9 . . ?
H9'1 C9' H9'2 108.9 . . ?
C9' C10' H10D 109.5 . . ?
C9' C10' H10E 109.5 . . ?
H10D C10' H10E 109.5 . . ?
C9' C10' H10F 109.5 . . ?
H10D C10' H10F 109.5 . . ?
H10E C10' H10F 109.5 . . ?
O3 C11' C12' 110.1(12) . . ?
O3 C11' H11C 109.6 . . ?
C12' C11' H11C 109.6 . . ?
O3 C11' H11D 109.6 . . ?
C12' C11' H11D 109.6 . . ?
H11C C11' H11D 108.2 . . ?
C11' C12' H12D 109.5 . . ?
C11' C12' H12E 109.5 . . ?
H12D C12' H12E 109.5 . . ?
C11' C12' H12F 109.5 . . ?
H12D C12' H12F 109.5 . . ?
H12E C12' H12F 109.5 . . ?
O4 C13 O5 126.3(2) . . ?
O4 C13 N1 123.5(2) . . ?
O5 C13 N1 110.1(2) . . ?
O5 C14 C16 110.7(2) . . ?
O5 C14 C15 108.7(2) . . ?
C16 C14 C15 113.5(3) . . ?
O5 C14 C17 102.8(2) . . ?
C16 C14 C17 110.6(3) . . ?
C15 C14 C17 110.0(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 P1 O2 C9 -2.3(4) . . . . ?
O3 P1 O2 C9 -129.8(4) . . . . ?
C8 P1 O2 C9 123.5(3) . . . . ?
O1 P1 O2 C9' 52.5(6) . . . . ?
O3 P1 O2 C9' -75.0(6) . . . . ?
C8 P1 O2 C9' 178.3(6) . . . . ?
O1 P1 O3 C11 -44.7(3) . . . . ?
O2 P1 O3 C11 82.5(3) . . . . ?
C8 P1 O3 C11 -167.9(3) . . . . ?
O1 P1 O3 C11' 33.0(11) . . . . ?
O2 P1 O3 C11' 160.1(11) . . . . ?
C8 P1 O3 C11' -90.3(11) . . . . ?
C13 N1 C1 C6 -154.3(2) . . . . ?
C8 N1 C1 C6 11.3(2) . . . . ?
C13 N1 C1 C2 26.7(4) . . . . ?
C8 N1 C1 C2 -167.7(2) . . . . ?
C6 C1 C2 C3 0.3(4) . . . . ?
N1 C1 C2 C3 179.2(2) . . . . ?
C1 C2 C3 C4 -0.2(4) . . . . ?
C2 C3 C4 C5 0.0(5) . . . . ?
C2 C3 C4 F1 179.9(2) . . . . ?
C3 C4 C5 C6 0.0(5) . . . . ?
F1 C4 C5 C6 -179.8(3) . . . . ?
C4 C5 C6 C1 0.1(4) . . . . ?
C4 C5 C6 C7 178.8(3) . . . . ?
C2 C1 C6 C5 -0.3(4) . . . . ?
N1 C1 C6 C5 -179.4(2) . . . . ?
C2 C1 C6 C7 -179.2(2) . . . . ?
N1 C1 C6 C7 1.8(3) . . . . ?
C5 C6 C7 C8 168.1(2) . . . . ?
C1 C6 C7 C8 -13.2(3) . . . . ?
C13 N1 C8 C7 146.4(2) . . . . ?
C1 N1 C8 C7 -18.9(2) . . . . ?
C13 N1 C8 P1 -94.2(2) . . . . ?
C1 N1 C8 P1 100.47(18) . . . . ?
C6 C7 C8 N1 18.9(2) . . . . ?
C6 C7 C8 P1 -102.43(18) . . . . ?
O1 P1 C8 N1 177.21(16) . . . . ?
O2 P1 C8 N1 49.69(19) . . . . ?
O3 P1 C8 N1 -57.32(19) . . . . ?
O1 P1 C8 C7 -66.8(2) . . . . ?
O2 P1 C8 C7 165.72(16) . . . . ?
O3 P1 C8 C7 58.71(19) . . . . ?
C9' O2 C9 C10 26.2(9) . . . . ?
P1 O2 C9 C10 113.4(6) . . . . ?
C11' O3 C11 C12 9.2(11) . . . . ?
P1 O3 C11 C12 139.7(5) . . . . ?
C9 O2 C9' C10' -37.7(8) . . . . ?
P1 O2 C9' C10' -160.2(9) . . . . ?
C11 O3 C11' C12' -18.9(8) . . . . ?
P1 O3 C11' C12' -124.4(10) . . . . ?
C14 O5 C13 O4 2.8(4) . . . . ?
C14 O5 C13 N1 -178.0(2) . . . . ?
C1 N1 C13 O4 -12.6(4) . . . . ?
C8 N1 C13 O4 -175.8(2) . . . . ?
C1 N1 C13 O5 168.2(2) . . . . ?
C8 N1 C13 O5 5.0(3) . . . . ?
C13 O5 C14 C16 -59.3(4) . . . . ?
C13 O5 C14 C15 66.0(3) . . . . ?
C13 O5 C14 C17 -177.4(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C2 H2 O4 0.93 2.44 2.920(3) 112.2 .
C7 H7A O1 0.97 2.62 3.423(3) 140.1 2_666
C10' H10E F1 0.96 2.34 3.226(14) 153.7 1_654
C15 H15A O4 0.96 2.51 3.056(4) 116.3 .
C16 H16C O4 0.96 2.42 2.937(4) 113.1 .

_refine_diff_density_max         0.244
_refine_diff_density_min         -0.215
_refine_diff_density_rms         0.034

_shelxl_version_number           2013-4

