# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_ABS
_database_code_depnum_ccdc_archive 'CCDC 1424911'
_audit_update_record             
;
2015-09-16 deposited with the CCDC.
2015-11-13 downloaded from the CCDC.
;


_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H24 N2 O4 P1'
_chemical_formula_sum            'C15 H24 N2 O4 P'
_chemical_formula_weight         327.33
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_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                   9.6789(5)
_cell_length_b                   9.1089(4)
_cell_length_c                   20.6717(9)
_cell_angle_alpha                90
_cell_angle_beta                 93.303(2)
_cell_angle_gamma                90
_cell_volume                     1819.48(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    4330
_cell_measurement_theta_min      2.38
_cell_measurement_theta_max      22.63
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             700
_exptl_special_details           
;
 ?
;

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.169
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
  [Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.891
_exptl_absorpt_correction_T_max  0.911

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_orient_matrix_type       'by SAINT Bruker-AXS'
_diffrn_orient_matrix_ub_11      0.999777E-1
_diffrn_orient_matrix_ub_12      0.119869E-1
_diffrn_orient_matrix_ub_13      0.140206E-1
_diffrn_orient_matrix_ub_21      0.51735E-2
_diffrn_orient_matrix_ub_22      0.889331E-1
_diffrn_orient_matrix_ub_23      -0.281202E-1
_diffrn_orient_matrix_ub_31      -0.262255E-1
_diffrn_orient_matrix_ub_32      0.632408E-1
_diffrn_orient_matrix_ub_33      0.368869E-1
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.053
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_number            13849
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         26.07
_diffrn_reflns_theta_full        26.07
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             3602
_reflns_number_gt                2291
_reflns_threshold_expression     >2sigma(I)
#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker APEX2 (Bruker, 2011)'
_computing_cell_refinement       'Bruker APEX2 (Bruker, 2011)'
_computing_data_reduction        'Bruker APEX2 (Bruker, 2011)'
_computing_structure_solution    'SIR92 (Giacovazzo et al, 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_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)+(0.1377P)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    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3602
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0977
_refine_ls_R_factor_gt           0.0675
_refine_ls_wR_factor_ref         0.216
_refine_ls_wR_factor_gt          0.1907
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.343
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.061

#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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 0.006 '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'

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
C1 C 0.7280(3) 0.3999(3) 0.75144(12) 0.0510(6) Uani 1 1 d . . .
C2 C 0.5867(3) 0.3290(3) 0.84002(12) 0.0519(6) Uani 1 1 d . . .
H2 H 0.549 0.4286 0.8359 0.062 Uiso 1 1 calc R . .
C3 C 0.6794(3) 0.3238(3) 0.90109(12) 0.0542(6) Uani 1 1 d . . .
C4 C 0.7837(3) 0.2226(3) 0.91031(15) 0.0687(8) Uani 1 1 d . . .
H4 H 0.8006 0.157 0.8772 0.082 Uiso 1 1 calc R . .
C5 C 0.8637(4) 0.2160(4) 0.96732(18) 0.0906(11) Uani 1 1 d . . .
H5 H 0.9345 0.147 0.9716 0.109 Uiso 1 1 calc R . .
C6 C 0.8412(5) 0.3100(4) 1.01880(17) 0.0942(11) Uani 1 1 d . . .
C7 C 0.7373(5) 0.4100(4) 1.00928(16) 0.0953(11) Uani 1 1 d . . .
H7 H 0.7191 0.4746 1.0426 0.114 Uiso 1 1 calc R . .
C8 C 0.6582(4) 0.4184(3) 0.95172(15) 0.0792(9) Uani 1 1 d . . .
H8 H 0.5891 0.4892 0.9469 0.095 Uiso 1 1 calc R . .
C9 C 0.9343(8) 0.2987(6) 1.0812(2) 0.162(3) Uani 1 1 d . . .
C10 C 0.9800(9) 0.4288(7) 1.1085(3) 0.210(4) Uani 1 1 d . . .
H10A H 1.0409 0.4089 1.1457 0.315 Uiso 1 1 calc R . .
H10B H 0.9022 0.4849 1.1213 0.315 Uiso 1 1 calc R . .
H10C H 1.0288 0.4836 1.0773 0.315 Uiso 1 1 calc R . .
C11 C 0.9208(9) 0.1634(7) 1.1156(2) 0.188(3) Uani 1 1 d . . .
H11A H 0.9898 0.1589 1.1508 0.282 Uiso 1 1 calc R . .
H11B H 0.9332 0.0825 1.0867 0.282 Uiso 1 1 calc R . .
H11C H 0.8304 0.1579 1.1323 0.282 Uiso 1 1 calc R . .
C14 C 0.3864(8) 0.1444(6) 0.9642(2) 0.164(3) Uani 1 1 d . . .
H14A H 0.3641 0.0473 0.9474 0.196 Uiso 1 1 calc R . .
H14B H 0.4834 0.1421 0.9789 0.196 Uiso 1 1 calc R . .
N1 N 0.8021(3) 0.3513(2) 0.70311(11) 0.0722(7) Uani 1 1 d . . .
H1A H 0.8486 0.4122 0.6812 0.087 Uiso 1 1 calc R . .
H1B H 0.8031 0.2592 0.694 0.087 Uiso 1 1 calc R . .
N2 N 0.6545(2) 0.2958(2) 0.78092(10) 0.0535(6) Uani 1 1 d . . .
H2A H 0.6478 0.2092 0.7645 0.064 Uiso 1 1 calc R . .
O1 O 0.4809(2) 0.0499(2) 0.83931(12) 0.0867(7) Uani 1 1 d . . .
O2 O 0.3766(2) 0.2398(2) 0.91083(10) 0.0760(6) Uani 1 1 d . . .
O3 O 0.3339(2) 0.2661(3) 0.79306(12) 0.0946(8) Uani 1 1 d . . .
O4 O 0.7228(2) 0.53001(18) 0.76657(9) 0.0663(6) Uani 1 1 d . . .
P1 P 0.44188(8) 0.20362(8) 0.84545(4) 0.0634(3) Uani 1 1 d . A .
C15 C 0.3190(9) 0.1598(6) 1.0145(3) 0.200(3) Uani 1 1 d . . .
H15A H 0.3316 0.2578 1.0309 0.3 Uiso 1 1 calc R . .
H15B H 0.3519 0.0906 1.0468 0.3 Uiso 1 1 calc R . .
H15C H 0.2225 0.1428 1.0038 0.3 Uiso 1 1 calc R . .
C12A C 0.224(3) 0.168(6) 0.771(2) 0.202(5) Uani 0.403(10) 1 d P A 1
H12A H 0.2699 0.0876 0.7503 0.242 Uiso 0.403(10) 1 calc PR A 1
H12B H 0.1882 0.1282 0.81 0.242 Uiso 0.403(10) 1 calc PR A 1
C13A C 0.1298(15) 0.195(2) 0.7377(10) 0.202(5) Uani 0.403(10) 1 d P A 1
H13A H 0.108 0.2975 0.7414 0.303 Uiso 0.403(10) 1 calc PR A 1
H13B H 0.0526 0.1374 0.7501 0.303 Uiso 0.403(10) 1 calc PR A 1
H13C H 0.1491 0.173 0.6938 0.303 Uiso 0.403(10) 1 calc PR A 1
C12B C 0.1960(18) 0.202(4) 0.7782(16) 0.202(5) Uani 0.597(10) 1 d P A 2
H12C H 0.1777 0.2206 0.7323 0.242 Uiso 0.597(10) 1 calc PR A 2
H12D H 0.2108 0.0968 0.7819 0.242 Uiso 0.597(10) 1 calc PR A 2
C13B C 0.1000(11) 0.2193(17) 0.7985(7) 0.202(5) Uani 0.597(10) 1 d P A 2
H13D H 0.1058 0.1884 0.843 0.303 Uiso 0.597(10) 1 calc PR A 2
H13E H 0.0296 0.1637 0.7748 0.303 Uiso 0.597(10) 1 calc PR A 2
H13F H 0.0771 0.3218 0.7962 0.303 Uiso 0.597(10) 1 calc PR A 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 O4 1.228(3) . ?
C1 N1 1.338(3) . ?
C1 N2 1.352(3) . ?
C2 N2 1.452(3) . ?
C2 C3 1.507(4) . ?
C2 P1 1.816(3) . ?
C2 H2 0.98 . ?
C3 C4 1.373(4) . ?
C3 C8 1.380(4) . ?
C4 C5 1.373(4) . ?
C4 H4 0.93 . ?
C5 C6 1.393(5) . ?
C5 H5 0.93 . ?
C6 C7 1.363(5) . ?
C6 C9 1.534(6) . ?
C7 C8 1.379(4) . ?
C7 H7 0.93 . ?
C8 H8 0.93 . ?
C9 C10 1.374(6) . ?
C9 C11 1.433(7) . ?
C10 H10A 0.96 . ?
C10 H10B 0.96 . ?
C10 H10C 0.96 . ?
C11 H11A 0.96 . ?
C11 H11B 0.96 . ?
C11 H11C 0.96 . ?
C14 C15 1.266(6) . ?
C14 O2 1.403(5) . ?
C14 H14A 0.97 . ?
C14 H14B 0.97 . ?
N1 H1A 0.86 . ?
N1 H1B 0.86 . ?
N2 H2A 0.86 . ?
O1 P1 1.457(2) . ?
O2 P1 1.560(2) . ?
O3 C12A 1.44(5) . ?
O3 C12B 1.47(3) . ?
O3 P1 1.568(3) . ?
C15 H15A 0.96 . ?
C15 H15B 0.96 . ?
C15 H15C 0.96 . ?
C12A C13A 1.14(3) . ?
C12A H12A 0.97 . ?
C12A H12B 0.97 . ?
C13A H13A 0.96 . ?
C13A H13B 0.96 . ?
C13A H13C 0.96 . ?
C12B C13B 1.05(2) . ?
C12B H12C 0.97 . ?
C12B H12D 0.97 . ?
C13B H13D 0.96 . ?
C13B H13E 0.96 . ?
C13B H13F 0.96 . ?

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
O4 C1 N1 122.8(2) . . ?
O4 C1 N2 122.1(2) . . ?
N1 C1 N2 115.1(2) . . ?
N2 C2 C3 115.0(2) . . ?
N2 C2 P1 107.98(16) . . ?
C3 C2 P1 110.65(17) . . ?
N2 C2 H2 107.6 . . ?
C3 C2 H2 107.6 . . ?
P1 C2 H2 107.6 . . ?
C4 C3 C8 117.0(3) . . ?
C4 C3 C2 122.4(2) . . ?
C8 C3 C2 120.6(2) . . ?
C3 C4 C5 121.5(3) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C4 C5 C6 121.6(3) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C7 C6 C5 116.5(3) . . ?
C7 C6 C9 124.0(4) . . ?
C5 C6 C9 119.5(4) . . ?
C6 C7 C8 122.0(3) . . ?
C6 C7 H7 119 . . ?
C8 C7 H7 119 . . ?
C7 C8 C3 121.3(3) . . ?
C7 C8 H8 119.3 . . ?
C3 C8 H8 119.3 . . ?
C10 C9 C11 125.2(4) . . ?
C10 C9 C6 116.5(4) . . ?
C11 C9 C6 114.1(5) . . ?
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 . . ?
C15 C14 O2 124.2(5) . . ?
C15 C14 H14A 106.3 . . ?
O2 C14 H14A 106.3 . . ?
C15 C14 H14B 106.3 . . ?
O2 C14 H14B 106.3 . . ?
H14A C14 H14B 106.4 . . ?
C1 N1 H1A 120 . . ?
C1 N1 H1B 120 . . ?
H1A N1 H1B 120 . . ?
C1 N2 C2 120.58(19) . . ?
C1 N2 H2A 119.7 . . ?
C2 N2 H2A 119.7 . . ?
C14 O2 P1 122.5(3) . . ?
C12A O3 P1 116.3(17) . . ?
C12B O3 P1 124.0(12) . . ?
O1 P1 O2 113.48(13) . . ?
O1 P1 O3 117.02(15) . . ?
O2 P1 O3 103.56(13) . . ?
O1 P1 C2 113.22(12) . . ?
O2 P1 C2 105.85(12) . . ?
O3 P1 C2 102.40(13) . . ?
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 . . ?
C13A C12A O3 128(4) . . ?
C13A C12A H12A 105.4 . . ?
O3 C12A H12A 105.4 . . ?
C13A C12A H12B 105.4 . . ?
O3 C12A H12B 105.4 . . ?
H12A C12A H12B 106 . . ?
C13B C12B O3 132(3) . . ?
C13B C12B H12C 104.3 . . ?
O3 C12B H12C 104.3 . . ?
C13B C12B H12D 104.3 . . ?
O3 C12B H12D 104.3 . . ?
H12C C12B H12D 105.6 . . ?
C12B C13B H13D 109.5 . . ?
C12B C13B H13E 109.5 . . ?
H13D C13B H13E 109.5 . . ?
C12B C13B H13F 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 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
N2 C2 C3 C4 -36.7(3) . . . . ?
P1 C2 C3 C4 86.0(3) . . . . ?
N2 C2 C3 C8 146.1(3) . . . . ?
P1 C2 C3 C8 -91.2(3) . . . . ?
C8 C3 C4 C5 -0.2(5) . . . . ?
C2 C3 C4 C5 -177.4(3) . . . . ?
C3 C4 C5 C6 1.0(6) . . . . ?
C4 C5 C6 C7 -0.9(6) . . . . ?
C4 C5 C6 C9 -179.6(4) . . . . ?
C5 C6 C7 C8 -0.1(6) . . . . ?
C9 C6 C7 C8 178.5(5) . . . . ?
C6 C7 C8 C3 1.0(6) . . . . ?
C4 C3 C8 C7 -0.8(5) . . . . ?
C2 C3 C8 C7 176.5(3) . . . . ?
C7 C6 C9 C10 -42.3(10) . . . . ?
C5 C6 C9 C10 136.3(7) . . . . ?
C7 C6 C9 C11 115.9(7) . . . . ?
C5 C6 C9 C11 -65.5(8) . . . . ?
O4 C1 N2 C2 -11.9(4) . . . . ?
N1 C1 N2 C2 170.6(2) . . . . ?
C3 C2 N2 C1 -81.2(3) . . . . ?
P1 C2 N2 C1 154.68(19) . . . . ?
C15 C14 O2 P1 -169.6(7) . . . . ?
C14 O2 P1 O1 15.0(4) . . . . ?
C14 O2 P1 O3 142.9(4) . . . . ?
C14 O2 P1 C2 -109.7(4) . . . . ?
C12A O3 P1 O1 37(2) . . . . ?
C12B O3 P1 O1 55.5(17) . . . . ?
C12A O3 P1 O2 -88(2) . . . . ?
C12B O3 P1 O2 -70.2(17) . . . . ?
C12A O3 P1 C2 162(2) . . . . ?
C12B O3 P1 C2 179.9(17) . . . . ?
N2 C2 P1 O1 52.9(2) . . . . ?
C3 C2 P1 O1 -73.7(2) . . . . ?
N2 C2 P1 O2 177.85(16) . . . . ?
C3 C2 P1 O2 51.19(19) . . . . ?
N2 C2 P1 O3 -74.0(2) . . . . ?
C3 C2 P1 O3 159.37(18) . . . . ?
C12B O3 C12A C13A 52(7) . . . . ?
P1 O3 C12A C13A 173(4) . . . . ?
C12A O3 C12B C13B 156(13) . . . . ?
P1 O3 C12B C13B 88(4) . . . . ?

