# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_r140114a1
_database_code_depnum_ccdc_archive 'CCDC 982309'
_audit_update_record             
;
2014-01-20 deposited with the CCDC.
2016-07-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H25 N2 O5 P'
_chemical_formula_weight         440.42

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   Pbca

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

_cell_length_a                   14.067(3)
_cell_length_b                   17.217(3)
_cell_length_c                   18.001(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4359.7(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9902
_cell_measurement_theta_min      2.1821
_cell_measurement_theta_max      27.8804

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1856
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9680
_exptl_absorpt_correction_T_max  0.9806
_exptl_absorpt_process_details   crystalclear

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  confocal
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            33067
_diffrn_reflns_av_R_equivalents  0.1935
_diffrn_reflns_av_sigmaI/netI    0.0932
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.19
_diffrn_reflns_theta_max         25.02
_reflns_number_total             3797
_reflns_number_gt                2736
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       crystalclear
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1381P)²+1.9077P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0096(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3797
_refine_ls_number_parameters     312
_refine_ls_number_restraints     103
_refine_ls_R_factor_all          0.1314
_refine_ls_R_factor_gt           0.0992
_refine_ls_wR_factor_ref         0.2509
_refine_ls_wR_factor_gt          0.2308
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.004
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P -0.02067(8) 0.35192(8) 0.09119(7) 0.0518(4) Uani 1 1 d D . .
O1 O 0.2567(3) 0.2437(3) 0.0736(2) 0.0865(13) Uani 1 1 d . . .
O2 O 0.1365(2) 0.39047(18) 0.2649(2) 0.0584(9) Uani 1 1 d . . .
O3 O -0.0028(3) 0.3062(3) 0.02239(18) 0.0898(15) Uani 1 1 d . A .
O5 O -0.12408(19) 0.38569(16) 0.09734(16) 0.0437(7) Uani 1 1 d . A .
N1 N 0.1729(2) 0.30319(19) 0.16971(18) 0.0433(9) Uani 1 1 d . A .
N2 N 0.0714(3) 0.1885(2) 0.3803(2) 0.0448(9) Uani 1 1 d D A .
H2 H 0.046(3) 0.183(3) 0.4257(12) 0.054 Uiso 1 1 d D . .
C1 C 0.2470(3) 0.2948(3) 0.1182(3) 0.0588(13) Uani 1 1 d . . .
C2 C 0.3155(3) 0.3596(3) 0.1341(3) 0.0617(14) Uani 1 1 d . . .
C3 C 0.4006(4) 0.3772(4) 0.0982(4) 0.090(2) Uani 1 1 d . . .
H3A H 0.4229 0.3492 0.0562 0.108 Uiso 1 1 calc R . .
C4 C 0.4508(5) 0.4400(5) 0.1294(6) 0.115(3) Uani 1 1 d . . .
H4A H 0.5103 0.4542 0.1085 0.138 Uiso 1 1 calc R . .
C5 C 0.4164(5) 0.4816(4) 0.1893(6) 0.105(3) Uani 1 1 d . . .
H5A H 0.4525 0.5241 0.2077 0.126 Uiso 1 1 calc R . .
C6 C 0.3315(4) 0.4633(3) 0.2233(4) 0.0822(19) Uani 1 1 d . . .
H6 H 0.3084 0.4916 0.2649 0.099 Uiso 1 1 calc R . .
C7 C 0.2816(3) 0.4011(3) 0.1931(3) 0.0611(14) Uani 1 1 d . . .
C8 C 0.1887(3) 0.3675(2) 0.2165(3) 0.0470(10) Uani 1 1 d . . .
C9 C 0.0894(3) 0.2506(2) 0.1834(2) 0.0381(9) Uani 1 1 d . . .
C10 C 0.0884(3) 0.1817(3) 0.1273(2) 0.0487(11) Uani 1 1 d . A .
H10A H 0.1469 0.1513 0.1327 0.073 Uiso 1 1 calc R . .
H10B H 0.0843 0.2021 0.0765 0.073 Uiso 1 1 calc R . .
H10C H 0.0333 0.1485 0.1372 0.073 Uiso 1 1 calc R . .
C11 C -0.0024(3) 0.2982(2) 0.1754(2) 0.0366(9) Uani 1 1 d . A .
H11A H -0.0050 0.3354 0.2173 0.044 Uiso 1 1 calc R . .
H11B H -0.0567 0.2621 0.1814 0.044 Uiso 1 1 calc R . .
O4 O 0.0471(4) 0.4200(3) 0.0803(4) 0.0479(15) Uani 0.594(8) 1 d PDU A 1
C12 C 0.0295(6) 0.4882(5) 0.1250(5) 0.0552(19) Uani 0.594(8) 1 d PDU A 1
H12A H 0.0338 0.4754 0.1785 0.066 Uiso 0.594(8) 1 calc PR A 1
H12B H -0.0346 0.5093 0.1147 0.066 Uiso 0.594(8) 1 calc PR A 1
C13 C 0.1064(9) 0.5477(9) 0.1036(10) 0.056(3) Uani 0.594(8) 1 d PDU A 1
H13A H 0.0980 0.5950 0.1331 0.084 Uiso 0.594(8) 1 calc PR A 1
H13B H 0.1008 0.5602 0.0507 0.084 Uiso 0.594(8) 1 calc PR A 1
H13C H 0.1694 0.5256 0.1135 0.084 Uiso 0.594(8) 1 calc PR A 1
O4' O 0.0336(6) 0.4329(4) 0.1212(5) 0.051(2) Uani 0.406(8) 1 d PDU A 2
C12' C 0.0444(8) 0.5025(6) 0.0761(7) 0.052(2) Uani 0.406(8) 1 d PDU A 2
H12C H -0.0135 0.5349 0.0805 0.062 Uiso 0.406(8) 1 calc PR A 2
H12D H 0.0519 0.4876 0.0233 0.062 Uiso 0.406(8) 1 calc PR A 2
C13' C 0.1310(16) 0.5496(17) 0.1009(19) 0.075(5) Uani 0.406(8) 1 d PDU A 2
H13D H 0.1373 0.5958 0.0695 0.112 Uiso 0.406(8) 1 calc PR A 2
H13E H 0.1884 0.5176 0.0963 0.112 Uiso 0.406(8) 1 calc PR A 2
H13F H 0.1229 0.5655 0.1528 0.112 Uiso 0.406(8) 1 calc PR A 2
C14 C -0.2051(3) 0.3346(3) 0.0881(3) 0.0564(12) Uani 1 1 d . . .
H14A H -0.2191 0.3079 0.1356 0.068 Uiso 1 1 calc R A .
H14B H -0.1907 0.2946 0.0502 0.068 Uiso 1 1 calc R . .
C15 C -0.2894(3) 0.3816(3) 0.0643(3) 0.0647(14) Uani 1 1 d . A .
H15A H -0.3442 0.3472 0.0572 0.097 Uiso 1 1 calc R . .
H15B H -0.2749 0.4081 0.0174 0.097 Uiso 1 1 calc R . .
H15C H -0.3042 0.4202 0.1025 0.097 Uiso 1 1 calc R . .
C16 C 0.0994(3) 0.2193(2) 0.2615(2) 0.0344(9) Uani 1 1 d . A .
C17 C 0.0362(3) 0.2237(2) 0.3179(2) 0.0421(10) Uani 1 1 d . . .
H17A H -0.0243 0.2480 0.3147 0.051 Uiso 1 1 calc R A .
C18 C 0.1605(3) 0.1610(2) 0.3654(2) 0.0406(10) Uani 1 1 d . . .
C19 C 0.2245(4) 0.1226(2) 0.4117(2) 0.0505(11) Uani 1 1 d . A .
H19A H 0.2091 0.1112 0.4619 0.061 Uiso 1 1 calc R . .
C20 C 0.3113(4) 0.1016(3) 0.3815(3) 0.0560(12) Uani 1 1 d . . .
H20A H 0.3567 0.0756 0.4116 0.067 Uiso 1 1 calc R A .
C21 C 0.3331(3) 0.1180(3) 0.3077(3) 0.0529(12) Uani 1 1 d . A .
H21A H 0.3930 0.1023 0.2885 0.064 Uiso 1 1 calc R . .
C22 C 0.2702(3) 0.1565(2) 0.2615(2) 0.0427(10) Uani 1 1 d . . .
H22A H 0.2864 0.1675 0.2114 0.051 Uiso 1 1 calc R A .
C23 C 0.1814(3) 0.1788(2) 0.2909(2) 0.0351(9) Uani 1 1 d . A .


_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 1.489(4) . ?
P1 O4 1.524(5) . ?
P1 O5 1.570(3) . ?
P1 O4' 1.679(7) . ?
P1 C11 1.795(4) . ?
O1 C1 1.200(6) . ?
O2 C8 1.206(5) . ?
O5 C14 1.449(5) . ?
N1 C1 1.403(6) . ?
N1 C8 1.409(6) . ?
N1 C9 1.503(5) . ?
N2 C18 1.366(5) . ?
N2 C17 1.369(5) . ?
C1 C2 1.502(8) . ?
C2 C7 1.367(8) . ?
C2 C3 1.394(7) . ?
C3 C4 1.407(11) . ?
C4 C5 1.383(12) . ?
C5 C6 1.379(10) . ?
C6 C7 1.392(7) . ?
C7 C8 1.490(6) . ?
C9 C16 1.512(5) . ?
C9 C11 1.536(5) . ?
C9 C10 1.557(6) . ?
O4 C12 1.446(8) . ?
C12 C13 1.537(9) . ?
O4' C12' 1.455(8) . ?
C12' C13' 1.530(10) . ?
C14 C15 1.499(6) . ?
C16 C17 1.352(5) . ?
C16 C23 1.447(5) . ?
C18 C19 1.394(6) . ?
C18 C23 1.407(6) . ?
C19 C20 1.385(7) . ?
C20 C21 1.392(7) . ?
C21 C22 1.383(6) . ?
C22 C23 1.410(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 P1 O4 101.2(3) . . ?
O3 P1 O5 114.3(2) . . ?
O4 P1 O5 107.7(2) . . ?
O3 P1 O4' 129.1(4) . . ?
O4 P1 O4' 28.2(3) . . ?
O5 P1 O4' 95.2(4) . . ?
O3 P1 C11 113.9(2) . . ?
O4 P1 C11 114.6(3) . . ?
O5 P1 C11 105.33(17) . . ?
O4' P1 C11 95.2(3) . . ?
C14 O5 P1 119.7(3) . . ?
C1 N1 C8 111.0(4) . . ?
C1 N1 C9 128.8(4) . . ?
C8 N1 C9 119.9(3) . . ?
C18 N2 C17 108.9(3) . . ?
O1 C1 N1 127.1(5) . . ?
O1 C1 C2 126.8(5) . . ?
N1 C1 C2 106.0(4) . . ?
C7 C2 C3 123.2(6) . . ?
C7 C2 C1 108.2(4) . . ?
C3 C2 C1 128.7(6) . . ?
C2 C3 C4 114.4(7) . . ?
C5 C4 C3 122.3(6) . . ?
C6 C5 C4 122.0(7) . . ?
C5 C6 C7 116.1(8) . . ?
C2 C7 C6 122.0(5) . . ?
C2 C7 C8 108.9(4) . . ?
C6 C7 C8 129.2(6) . . ?
O2 C8 N1 126.4(4) . . ?
O2 C8 C7 127.6(4) . . ?
N1 C8 C7 105.9(4) . . ?
N1 C9 C16 107.1(3) . . ?
N1 C9 C11 108.6(3) . . ?
C16 C9 C11 110.8(3) . . ?
N1 C9 C10 111.1(3) . . ?
C16 C9 C10 109.5(3) . . ?
C11 C9 C10 109.7(3) . . ?
C9 C11 P1 118.4(3) . . ?
C12 O4 P1 116.5(5) . . ?
O4 C12 C13 106.3(9) . . ?
C12' O4' P1 123.5(7) . . ?
O4' C12' C13' 110.9(15) . . ?
O5 C14 C15 109.1(4) . . ?
C17 C16 C23 106.1(3) . . ?
C17 C16 C9 128.1(4) . . ?
C23 C16 C9 125.8(3) . . ?
C16 C17 N2 110.7(4) . . ?
N2 C18 C19 129.7(4) . . ?
N2 C18 C23 107.7(3) . . ?
C19 C18 C23 122.6(4) . . ?
C20 C19 C18 117.3(4) . . ?
C19 C20 C21 121.0(4) . . ?
C22 C21 C20 122.0(4) . . ?
C21 C22 C23 118.2(4) . . ?
C18 C23 C22 118.9(4) . . ?
C18 C23 C16 106.6(3) . . ?
C22 C23 C16 134.5(4) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O3 P1 O5 C14 52.1(4) . . . . ?
O4 P1 O5 C14 163.6(4) . . . . ?
O4' P1 O5 C14 -170.6(4) . . . . ?
C11 P1 O5 C14 -73.7(3) . . . . ?
C8 N1 C1 O1 175.9(5) . . . . ?
C9 N1 C1 O1 1.5(8) . . . . ?
C8 N1 C1 C2 0.0(5) . . . . ?
C9 N1 C1 C2 -174.3(4) . . . . ?
O1 C1 C2 C7 -174.6(5) . . . . ?
N1 C1 C2 C7 1.3(5) . . . . ?
O1 C1 C2 C3 4.5(9) . . . . ?
N1 C1 C2 C3 -179.7(5) . . . . ?
C7 C2 C3 C4 2.0(8) . . . . ?
C1 C2 C3 C4 -176.9(5) . . . . ?
C2 C3 C4 C5 -1.7(9) . . . . ?
C3 C4 C5 C6 1.2(10) . . . . ?
C4 C5 C6 C7 -0.8(9) . . . . ?
C3 C2 C7 C6 -1.8(8) . . . . ?
C1 C2 C7 C6 177.3(4) . . . . ?
C3 C2 C7 C8 178.9(4) . . . . ?
C1 C2 C7 C8 -2.0(5) . . . . ?
C5 C6 C7 C2 1.1(7) . . . . ?
C5 C6 C7 C8 -179.7(5) . . . . ?
C1 N1 C8 O2 178.1(4) . . . . ?
C9 N1 C8 O2 -7.1(6) . . . . ?
C1 N1 C8 C7 -1.2(5) . . . . ?
C9 N1 C8 C7 173.7(3) . . . . ?
C2 C7 C8 O2 -177.2(5) . . . . ?
C6 C7 C8 O2 3.6(8) . . . . ?
C2 C7 C8 N1 2.0(5) . . . . ?
C6 C7 C8 N1 -177.2(4) . . . . ?
C1 N1 C9 C16 115.8(4) . . . . ?
C8 N1 C9 C16 -58.0(4) . . . . ?
C1 N1 C9 C11 -124.4(4) . . . . ?
C8 N1 C9 C11 61.7(4) . . . . ?
C1 N1 C9 C10 -3.7(6) . . . . ?
C8 N1 C9 C10 -177.6(3) . . . . ?
N1 C9 C11 P1 54.1(4) . . . . ?
C16 C9 C11 P1 171.5(3) . . . . ?
C10 C9 C11 P1 -67.5(4) . . . . ?
O3 P1 C11 C9 48.0(4) . . . . ?
O4 P1 C11 C9 -67.9(4) . . . . ?
O5 P1 C11 C9 174.0(3) . . . . ?
O4' P1 C11 C9 -89.2(5) . . . . ?
O3 P1 O4 C12 162.1(6) . . . . ?
O5 P1 O4 C12 41.9(7) . . . . ?
O4' P1 O4 C12 -24.8(8) . . . . ?
C11 P1 O4 C12 -74.9(6) . . . . ?
P1 O4 C12 C13 -179.8(8) . . . . ?
O3 P1 O4' C12' 52.5(12) . . . . ?
O4 P1 O4' C12' 43.8(9) . . . . ?
O5 P1 O4' C12' -74.8(10) . . . . ?
C11 P1 O4' C12' 179.3(10) . . . . ?
P1 O4' C12' C13' -153.8(16) . . . . ?
P1 O5 C14 C15 -156.1(3) . . . . ?
N1 C9 C16 C17 124.0(4) . . . . ?
C11 C9 C16 C17 5.7(6) . . . . ?
C10 C9 C16 C17 -115.4(4) . . . . ?
N1 C9 C16 C23 -55.1(5) . . . . ?
C11 C9 C16 C23 -173.4(3) . . . . ?
C10 C9 C16 C23 65.5(5) . . . . ?
C23 C16 C17 N2 -0.7(5) . . . . ?
C9 C16 C17 N2 -179.9(4) . . . . ?
C18 N2 C17 C16 0.9(5) . . . . ?
C17 N2 C18 C19 178.7(4) . . . . ?
C17 N2 C18 C23 -0.8(4) . . . . ?
N2 C18 C19 C20 -179.6(4) . . . . ?
C23 C18 C19 C20 -0.2(6) . . . . ?
C18 C19 C20 C21 -0.4(6) . . . . ?
C19 C20 C21 C22 0.7(7) . . . . ?
C20 C21 C22 C23 -0.4(6) . . . . ?
N2 C18 C23 C22 180.0(3) . . . . ?
C19 C18 C23 C22 0.5(6) . . . . ?
N2 C18 C23 C16 0.3(4) . . . . ?
C19 C18 C23 C16 -179.1(4) . . . . ?
C21 C22 C23 C18 -0.2(6) . . . . ?
C21 C22 C23 C16 179.3(4) . . . . ?
C17 C16 C23 C18 0.2(4) . . . . ?
C9 C16 C23 C18 179.5(3) . . . . ?
C17 C16 C23 C22 -179.3(4) . . . . ?
C9 C16 C23 C22 -0.1(7) . . . . ?

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
N2 H2 O3 0.898(10) 1.880(15) 2.764(5) 168(4) 8_566

_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_theta_full        25.02
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.416
_refine_diff_density_rms         0.079
####################################################################### 
# 
# 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_sa
_database_code_depnum_ccdc_archive 'CCDC 992526'
_audit_update_record             
;
2014-03-19 deposited with the CCDC.
2016-07-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H23 N2 O5 P'
_chemical_formula_weight         390.36

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   12.744(3)
_cell_length_b                   7.7256(15)
_cell_length_c                   20.770(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.09(3)
_cell_angle_gamma                90.00
_cell_volume                     1932.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    113(2)
_cell_measurement_reflns_used    5350
_cell_measurement_theta_min      1.6697
_cell_measurement_theta_max      27.9905

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    0.175
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9659
_exptl_absorpt_correction_T_max  0.9793
_exptl_absorpt_process_details   crystalclear

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      113(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  confocal
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            4619
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1127
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         28.04
_reflns_number_total             4619
_reflns_number_gt                2740
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       crystalclear
_computing_cell_refinement       crystalclear
_computing_data_reduction        crystalclear
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.000(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4619
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2171
_refine_ls_R_factor_gt           0.1972
_refine_ls_wR_factor_ref         0.5409
_refine_ls_wR_factor_gt          0.5345
_refine_ls_goodness_of_fit_ref   1.878
_refine_ls_restrained_S_all      1.878
_refine_ls_shift/su_max          5.211
_refine_ls_shift/su_mean         0.095

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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.8159(2) 0.5904(3) 0.11080(12) 0.0266(7) Uani 1 1 d . . .
O1 O 0.5944(5) 0.2313(9) 0.0638(3) 0.0287(15) Uani 1 1 d . . .
O2 O 0.9633(5) 0.1024(9) 0.1051(3) 0.0308(16) Uani 1 1 d . . .
O3 O 0.7994(6) 0.7732(9) 0.1238(3) 0.0333(17) Uani 1 1 d . . .
O4 O 0.9389(6) 0.5315(9) 0.1216(3) 0.0327(16) Uani 1 1 d . . .
O5 O 0.7526(5) 0.5330(8) 0.0347(3) 0.0289(15) Uani 1 1 d . . .
N1 N 0.7854(6) 0.1812(10) 0.1040(4) 0.0233(16) Uani 1 1 d . . .
N2 N 0.7137(8) -0.0102(12) 0.2020(4) 0.035(2) Uani 1 1 d . . .
C1 C 0.6764(8) 0.1766(12) 0.0539(5) 0.029(2) Uani 1 1 d . . .
C2 C 0.6895(8) 0.0925(12) -0.0059(4) 0.0252(19) Uani 1 1 d . . .
C3 C 0.6094(9) 0.0509(13) -0.0677(5) 0.031(2) Uani 1 1 d . . .
H3 H 0.5329 0.0743 -0.0756 0.037 Uiso 1 1 calc R . .
C4 C 0.6455(9) -0.0265(12) -0.1176(5) 0.032(2) Uani 1 1 d . . .
H4 H 0.5936 -0.0542 -0.1609 0.038 Uiso 1 1 calc R . .
C5 C 0.7560(10) -0.0622(14) -0.1038(5) 0.037(2) Uani 1 1 d . . .
H5 H 0.7791 -0.1159 -0.1380 0.044 Uiso 1 1 calc R . .
C6 C 0.8359(8) -0.0226(13) -0.0414(5) 0.030(2) Uani 1 1 d . . .
H6 H 0.9122 -0.0490 -0.0323 0.036 Uiso 1 1 calc R . .
C7 C 0.7989(8) 0.0556(12) 0.0058(5) 0.028(2) Uani 1 1 d . . .
C8 C 0.8640(8) 0.1133(12) 0.0769(5) 0.028(2) Uani 1 1 d . . .
C9 C 0.8020(7) 0.2555(12) 0.1731(4) 0.0247(19) Uani 1 1 d . . .
C10 C 0.7246(8) 0.1689(13) 0.2048(5) 0.028(2) Uani 1 1 d . . .
C11 C 0.6605(8) 0.2280(14) 0.2410(5) 0.034(2) Uani 1 1 d . . .
H11 H 0.6510 0.3462 0.2505 0.040 Uiso 1 1 calc R . .
C12 C 0.6108(9) 0.0880(15) 0.2622(5) 0.034(2) Uani 1 1 d . . .
H12 H 0.5631 0.0924 0.2890 0.041 Uiso 1 1 calc R . .
C13 C 0.6448(8) -0.0579(15) 0.2364(5) 0.034(2) Uani 1 1 d . . .
H13 H 0.6234 -0.1733 0.2419 0.041 Uiso 1 1 calc R . .
C14 C 0.9228(8) 0.2330(14) 0.2205(5) 0.029(2) Uani 1 1 d . . .
H14A H 0.9425 0.1099 0.2237 0.044 Uiso 1 1 calc R . .
H14B H 0.9298 0.2774 0.2659 0.044 Uiso 1 1 calc R . .
H14C H 0.9727 0.2973 0.2020 0.044 Uiso 1 1 calc R . .
C15 C 0.7722(8) 0.4514(11) 0.1670(5) 0.0252(19) Uani 1 1 d . . .
H15A H 0.8022 0.5013 0.2133 0.030 Uiso 1 1 calc R . .
H15B H 0.6903 0.4599 0.1533 0.030 Uiso 1 1 calc R . .
C16 C 1.0020(8) 0.6305(13) 0.0863(5) 0.029(2) Uani 1 1 d . . .
H16A H 1.0092 0.7527 0.1014 0.035 Uiso 1 1 calc R . .
H16B H 0.9638 0.6273 0.0364 0.035 Uiso 1 1 calc R . .
C17 C 1.1147(9) 0.5470(15) 0.1040(5) 0.038(2) Uani 1 1 d . . .
H17A H 1.1563 0.5680 0.1521 0.058 Uiso 1 1 calc R . .
H17B H 1.1552 0.5966 0.0756 0.058 Uiso 1 1 calc R . .
H17C H 1.1059 0.4221 0.0958 0.058 Uiso 1 1 calc R . .
C18 C 0.6442(7) 0.6064(12) -0.0019(5) 0.027(2) Uani 1 1 d . . .
H18A H 0.6486 0.7343 -0.0015 0.032 Uiso 1 1 calc R . .
H18B H 0.5895 0.5712 0.0202 0.032 Uiso 1 1 calc R . .
C19 C 0.6090(9) 0.5413(13) -0.0737(5) 0.031(2) Uani 1 1 d . . .
H19A H 0.6642 0.5750 -0.0949 0.047 Uiso 1 1 calc R . .
H19B H 0.5368 0.5914 -0.0995 0.047 Uiso 1 1 calc R . .
H19C H 0.6029 0.4149 -0.0737 0.047 Uiso 1 1 calc R . .
H2 H 0.762(7) -0.091(10) 0.190(4) 0.000(18) 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 1.466(7) . ?
P1 O4 1.576(7) . ?
P1 O5 1.585(7) . ?
P1 C15 1.803(9) . ?
O1 C1 1.205(11) . ?
O2 C8 1.211(11) . ?
O4 C16 1.467(11) . ?
O5 C18 1.456(10) . ?
N1 C1 1.438(11) . ?
N1 C8 1.401(12) . ?
N1 C9 1.495(11) . ?
N2 C10 1.390(13) . ?
N2 C13 1.353(13) . ?
N2 H2 0.96(8) . ?
C1 C2 1.460(13) . ?
C2 C7 1.364(13) . ?
C2 C3 1.391(12) . ?
C3 C4 1.399(15) . ?
C3 H3 0.9500 . ?
C4 C5 1.370(15) . ?
C4 H4 0.9500 . ?
C5 C6 1.396(14) . ?
C5 H5 0.9500 . ?
C6 C7 1.361(13) . ?
C6 H6 0.9500 . ?
C7 C8 1.505(13) . ?
C9 C10 1.510(13) . ?
C9 C14 1.542(12) . ?
C9 C15 1.556(12) . ?
C10 C11 1.358(14) . ?
C11 C12 1.395(15) . ?
C11 H11 0.9500 . ?
C12 C13 1.377(15) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.507(14) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 C19 1.496(13) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 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 O4 116.6(4) . . ?
O3 P1 O5 113.3(4) . . ?
O4 P1 O5 102.7(4) . . ?
O3 P1 C15 111.2(4) . . ?
O4 P1 C15 103.9(4) . . ?
O5 P1 C15 108.4(4) . . ?
C16 O4 P1 117.4(6) . . ?
C18 O5 P1 119.9(6) . . ?
C1 N1 C8 110.4(7) . . ?
C1 N1 C9 120.2(7) . . ?
C8 N1 C9 129.3(7) . . ?
C10 N2 C13 108.8(9) . . ?
C10 N2 H2 127(5) . . ?
C13 N2 H2 122(5) . . ?
O1 C1 N1 123.7(9) . . ?
O1 C1 C2 130.4(9) . . ?
N1 C1 C2 105.9(8) . . ?
C7 C2 C3 121.1(9) . . ?
C7 C2 C1 109.6(8) . . ?
C3 C2 C1 129.3(9) . . ?
C2 C3 C4 117.5(10) . . ?
C2 C3 H3 121.3 . . ?
C4 C3 H3 121.2 . . ?
C5 C4 C3 119.7(9) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 122.6(9) . . ?
C4 C5 H5 118.7 . . ?
C6 C5 H5 118.7 . . ?
C7 C6 C5 116.5(9) . . ?
C7 C6 H6 121.7 . . ?
C5 C6 H6 121.7 . . ?
C6 C7 C2 122.6(9) . . ?
C6 C7 C8 128.9(9) . . ?
C2 C7 C8 108.5(8) . . ?
O2 C8 N1 127.1(8) . . ?
O2 C8 C7 127.4(9) . . ?
N1 C8 C7 105.5(8) . . ?
N1 C9 C10 110.0(7) . . ?
N1 C9 C14 111.6(7) . . ?
C10 C9 C14 109.2(7) . . ?
N1 C9 C15 110.0(7) . . ?
C10 C9 C15 106.8(7) . . ?
C14 C9 C15 109.1(7) . . ?
C11 C10 N2 106.8(9) . . ?
C11 C10 C9 133.6(9) . . ?
N2 C10 C9 119.5(8) . . ?
C10 C11 C12 109.3(10) . . ?
C10 C11 H11 125.3 . . ?
C12 C11 H11 125.4 . . ?
C13 C12 C11 106.3(9) . . ?
C13 C12 H12 126.9 . . ?
C11 C12 H12 126.9 . . ?
C12 C13 N2 108.8(10) . . ?
C12 C13 H13 125.6 . . ?
N2 C13 H13 125.5 . . ?
C9 C14 H14A 109.5 . . ?
C9 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C9 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C9 C15 P1 120.9(6) . . ?
C9 C15 H15A 107.2 . . ?
P1 C15 H15A 107.2 . . ?
C9 C15 H15B 107.1 . . ?
P1 C15 H15B 107.1 . . ?
H15A C15 H15B 106.8 . . ?
O4 C16 C17 106.8(8) . . ?
O4 C16 H16A 110.4 . . ?
C17 C16 H16A 110.3 . . ?
O4 C16 H16B 110.4 . . ?
C17 C16 H16B 110.4 . . ?
H16A C16 H16B 108.6 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.4 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O5 C18 C19 108.3(8) . . ?
O5 C18 H18A 110.0 . . ?
C19 C18 H18A 110.0 . . ?
O5 C18 H18B 110.1 . . ?
C19 C18 H18B 110.0 . . ?
H18A C18 H18B 108.4 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 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 O4 C16 -52.7(8) . . . . ?
O5 P1 O4 C16 71.8(7) . . . . ?
C15 P1 O4 C16 -175.4(7) . . . . ?
O3 P1 O5 C18 -35.9(8) . . . . ?
O4 P1 O5 C18 -162.5(7) . . . . ?
C15 P1 O5 C18 88.0(7) . . . . ?
C8 N1 C1 O1 -178.1(9) . . . . ?
C9 N1 C1 O1 0.5(14) . . . . ?
C8 N1 C1 C2 3.0(10) . . . . ?
C9 N1 C1 C2 -178.3(7) . . . . ?
O1 C1 C2 C7 178.8(10) . . . . ?
N1 C1 C2 C7 -2.5(10) . . . . ?
O1 C1 C2 C3 -0.9(18) . . . . ?
N1 C1 C2 C3 177.8(9) . . . . ?
C7 C2 C3 C4 -1.3(14) . . . . ?
C1 C2 C3 C4 178.4(9) . . . . ?
C2 C3 C4 C5 1.6(14) . . . . ?
C3 C4 C5 C6 -0.7(15) . . . . ?
C4 C5 C6 C7 -0.6(15) . . . . ?
C5 C6 C7 C2 0.9(15) . . . . ?
C5 C6 C7 C8 179.9(9) . . . . ?
C3 C2 C7 C6 0.1(15) . . . . ?
C1 C2 C7 C6 -179.7(9) . . . . ?
C3 C2 C7 C8 -179.2(8) . . . . ?
C1 C2 C7 C8 1.0(11) . . . . ?
C1 N1 C8 O2 178.1(9) . . . . ?
C9 N1 C8 O2 -0.3(16) . . . . ?
C1 N1 C8 C7 -2.4(10) . . . . ?
C9 N1 C8 C7 179.1(8) . . . . ?
C6 C7 C8 O2 1.1(17) . . . . ?
C2 C7 C8 O2 -179.7(10) . . . . ?
C6 C7 C8 N1 -178.4(10) . . . . ?
C2 C7 C8 N1 0.8(10) . . . . ?
C1 N1 C9 C10 53.7(10) . . . . ?
C8 N1 C9 C10 -128.0(9) . . . . ?
C1 N1 C9 C14 175.0(8) . . . . ?
C8 N1 C9 C14 -6.7(13) . . . . ?
C1 N1 C9 C15 -63.8(10) . . . . ?
C8 N1 C9 C15 114.6(10) . . . . ?
C13 N2 C10 C11 -0.5(10) . . . . ?
C13 N2 C10 C9 177.0(8) . . . . ?
N1 C9 C10 C11 -137.7(10) . . . . ?
C14 C9 C10 C11 99.5(12) . . . . ?
C15 C9 C10 C11 -18.4(13) . . . . ?
N1 C9 C10 N2 45.5(11) . . . . ?
C14 C9 C10 N2 -77.2(10) . . . . ?
C15 C9 C10 N2 164.9(8) . . . . ?
N2 C10 C11 C12 1.1(11) . . . . ?
C9 C10 C11 C12 -175.9(9) . . . . ?
C10 C11 C12 C13 -1.3(11) . . . . ?
C11 C12 C13 N2 0.9(10) . . . . ?
C10 N2 C13 C12 -0.3(10) . . . . ?
N1 C9 C15 P1 -42.8(10) . . . . ?
C10 C9 C15 P1 -162.2(6) . . . . ?
C14 C9 C15 P1 79.9(8) . . . . ?
O3 P1 C15 C9 -168.1(7) . . . . ?
O4 P1 C15 C9 -41.9(8) . . . . ?
O5 P1 C15 C9 66.7(8) . . . . ?
P1 O4 C16 C17 -179.1(7) . . . . ?
P1 O5 C18 C19 175.2(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        28.04
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         1.148
_refine_diff_density_min         -1.073
_refine_diff_density_rms         0.282
