# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

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

data_190
_database_code_depnum_ccdc_archive 'CCDC 1444407'
_audit_update_record             
;
2015-12-28 deposited with the CCDC.
2017-05-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2012
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H17 N2 O4 P'
_chemical_formula_weight         332.29

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

_space_group_crystal_system      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                   9.5986(5)
_cell_length_b                   9.7691(5)
_cell_length_c                   10.0811(5)
_cell_angle_alpha                102.586(3)
_cell_angle_beta                 97.413(2)
_cell_angle_gamma                116.651(2)
_cell_volume                     796.21(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5758
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      25.85

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_F_000             348
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_exptl_absorpt_coefficient_mu    0.194
_shelx_estimated_absorpt_T_min   0.935
_shelx_estimated_absorpt_T_max   0.953
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.901
_exptl_absorpt_correction_T_max  0.962
_exptl_absorpt_process_details   'SADABS (Bruker, 1999)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16135
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.455
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2810
_reflns_number_gt                2107
_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       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014 (Sheldrick, 2014)'

_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)+(0.0404P)²+0.4505P]
 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       0.020(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2810
_refine_ls_number_parameters     212
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.1066
_refine_ls_wR_factor_gt          0.0903
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.0274(3) 0.1115(3) 0.3160(2) 0.0389(5) Uani 1 1 d . . . . .
C2 C -0.1008(3) 0.1438(3) 0.3049(2) 0.0377(5) Uani 1 1 d . . . . .
C3 C -0.1208(3) 0.2756(3) 0.3663(2) 0.0485(6) Uani 1 1 d . . . . .
H3 H -0.0351 0.3697 0.4305 0.058 Uiso 1 1 calc R U . . .
C4 C -0.2687(3) 0.2615(3) 0.3291(3) 0.0541(7) Uani 1 1 d . . . . .
H4 H -0.2845 0.3468 0.3694 0.065 Uiso 1 1 calc R U . . .
C5 C -0.3983(3) 0.1211(3) 0.2311(3) 0.0546(7) Uani 1 1 d . . . . .
H5 H -0.4981 0.1158 0.2088 0.066 Uiso 1 1 calc R U . . .
C6 C -0.3832(3) -0.0066(3) 0.1681(3) 0.0492(6) Uani 1 1 d . . . . .
H6 H -0.4698 -0.0983 0.1022 0.059 Uiso 1 1 calc R U . . .
C7 C -0.2311(3) 0.0042(3) 0.2061(2) 0.0386(5) Uani 1 1 d . . . . .
C8 C 0.0481(2) -0.1305(2) 0.1959(2) 0.0369(5) Uani 1 1 d . . . . .
C9 C 0.0929(3) -0.1914(3) 0.2937(2) 0.0487(6) Uani 1 1 d . . . . .
H9 H 0.0744 -0.1708 0.3823 0.058 Uiso 1 1 calc R U . . .
C10 C 0.1650(3) -0.2828(3) 0.2597(2) 0.0520(6) Uani 1 1 d . . . . .
H10 H 0.1965 -0.3233 0.3260 0.062 Uiso 1 1 calc R U . . .
C11 C 0.1914(3) -0.3152(3) 0.1282(2) 0.0403(5) Uani 1 1 d . . . . .
C12 C 0.1466(3) -0.2538(3) 0.0306(2) 0.0433(6) Uani 1 1 d . . . . .
H12 H 0.1648 -0.2745 -0.0582 0.052 Uiso 1 1 calc R U . . .
C13 C 0.0746(3) -0.1617(3) 0.0652(2) 0.0425(5) Uani 1 1 d . . . . .
H13 H 0.0436 -0.1203 -0.0006 0.051 Uiso 1 1 calc R U . . .
C14 C 0.2798(3) -0.4566(3) -0.0325(3) 0.0590(7) Uani 1 1 d . . . . .
H14A H 0.1762 -0.5092 -0.0990 0.088 Uiso 1 1 calc R U . . .
H14B H 0.3213 -0.5300 -0.0366 0.088 Uiso 1 1 calc R U . . .
H14C H 0.3529 -0.3641 -0.0549 0.088 Uiso 1 1 calc R U . . .
C15 C 0.4331(4) 0.1975(5) 0.5676(4) 0.0986(12) Uani 1 1 d . . . . .
H15A H 0.5058 0.2695 0.5259 0.148 Uiso 1 1 calc R U . . .
H15B H 0.4436 0.1025 0.5532 0.148 Uiso 1 1 calc R U . . .
H15C H 0.4589 0.2501 0.6667 0.148 Uiso 1 1 calc R U . . .
C16 C 0.3613(4) 0.3444(4) 0.2151(3) 0.0816(9) Uani 1 1 d . . . . .
H16A H 0.2987 0.3979 0.2273 0.122 Uiso 1 1 calc R U . . .
H16B H 0.3289 0.2791 0.1187 0.122 Uiso 1 1 calc R U . . .
H16C H 0.4737 0.4233 0.2395 0.122 Uiso 1 1 calc R U . . .
N1 N -0.1899(2) -0.1083(2) 0.15760(19) 0.0421(5) Uani 1 1 d . . . . .
N2 N -0.0335(2) -0.0400(2) 0.22669(17) 0.0369(4) Uani 1 1 d . . . . .
O1 O 0.2636(2) -0.4070(2) 0.10505(18) 0.0562(5) Uani 1 1 d . . . . .
O2 O 0.2535(2) 0.4023(2) 0.4807(2) 0.0782(6) Uani 1 1 d . . . . .
O3 O 0.2706(2) 0.1534(2) 0.50341(18) 0.0655(5) Uani 1 1 d . . . . .
O4 O 0.33542(19) 0.24476(19) 0.30405(17) 0.0499(4) Uani 1 1 d . . . . .
P1 P 0.23148(7) 0.24554(8) 0.41049(6) 0.0475(2) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N2 1.360(3) . ?
C1 C2 1.398(3) . ?
C1 P1 1.770(2) . ?
C2 C7 1.404(3) . ?
C2 C3 1.409(3) . ?
C3 C4 1.356(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.402(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.349(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.410(3) . ?
C6 H6 0.9300 . ?
C7 N1 1.346(3) . ?
C8 C13 1.369(3) . ?
C8 C9 1.374(3) . ?
C8 N2 1.435(3) . ?
C9 C10 1.369(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.378(3) . ?
C10 H10 0.9300 . ?
C11 O1 1.360(2) . ?
C11 C12 1.376(3) . ?
C12 C13 1.376(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 O1 1.418(3) . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 O3 1.433(3) . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 O4 1.426(3) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
N1 N2 1.346(2) . ?
O2 P1 1.4450(19) . ?
O3 P1 1.5521(19) . ?
O4 P1 1.5577(17) . ?

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
N2 C1 C2 105.43(18) . . ?
N2 C1 P1 126.58(16) . . ?
C2 C1 P1 127.67(16) . . ?
C1 C2 C7 104.88(18) . . ?
C1 C2 C3 135.2(2) . . ?
C7 C2 C3 120.0(2) . . ?
C4 C3 C2 118.1(2) . . ?
C4 C3 H3 121.0 . . ?
C2 C3 H3 121.0 . . ?
C3 C4 C5 121.5(2) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 122.2(2) . . ?
C6 C5 H5 118.9 . . ?
C4 C5 H5 118.9 . . ?
C5 C6 C7 117.4(2) . . ?
C5 C6 H6 121.3 . . ?
C7 C6 H6 121.3 . . ?
N1 C7 C2 111.88(19) . . ?
N1 C7 C6 127.3(2) . . ?
C2 C7 C6 120.8(2) . . ?
C13 C8 C9 120.2(2) . . ?
C13 C8 N2 119.05(19) . . ?
C9 C8 N2 120.64(19) . . ?
C10 C9 C8 119.5(2) . . ?
C10 C9 H9 120.2 . . ?
C8 C9 H9 120.2 . . ?
C9 C10 C11 120.6(2) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
O1 C11 C12 124.3(2) . . ?
O1 C11 C10 116.0(2) . . ?
C12 C11 C10 119.8(2) . . ?
C11 C12 C13 119.5(2) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C8 C13 C12 120.4(2) . . ?
C8 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
O1 C14 H14A 109.5 . . ?
O1 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O1 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O4 C16 H16A 109.5 . . ?
O4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C7 N1 N2 103.98(16) . . ?
N1 N2 C1 113.82(16) . . ?
N1 N2 C8 117.76(16) . . ?
C1 N2 C8 128.39(18) . . ?
C11 O1 C14 118.23(19) . . ?
C15 O3 P1 122.06(19) . . ?
C16 O4 P1 120.98(17) . . ?
O2 P1 O3 117.69(12) . . ?
O2 P1 O4 114.87(11) . . ?
O3 P1 O4 101.87(10) . . ?
O2 P1 C1 110.59(11) . . ?
O3 P1 C1 103.82(10) . . ?
O4 P1 C1 106.84(9) . . ?

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 C1 C2 C7 -0.3(2) . . . . ?
P1 C1 C2 C7 173.45(17) . . . . ?
N2 C1 C2 C3 -179.6(2) . . . . ?
P1 C1 C2 C3 -5.9(4) . . . . ?
C1 C2 C3 C4 -179.5(2) . . . . ?
C7 C2 C3 C4 1.2(3) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
C3 C4 C5 C6 -0.4(4) . . . . ?
C4 C5 C6 C7 1.1(4) . . . . ?
C1 C2 C7 N1 -0.1(2) . . . . ?
C3 C2 C7 N1 179.36(19) . . . . ?
C1 C2 C7 C6 180.0(2) . . . . ?
C3 C2 C7 C6 -0.6(3) . . . . ?
C5 C6 C7 N1 179.5(2) . . . . ?
C5 C6 C7 C2 -0.6(3) . . . . ?
C13 C8 C9 C10 0.4(4) . . . . ?
N2 C8 C9 C10 177.4(2) . . . . ?
C8 C9 C10 C11 -0.6(4) . . . . ?
C9 C10 C11 O1 -179.9(2) . . . . ?
C9 C10 C11 C12 0.7(4) . . . . ?
O1 C11 C12 C13 -179.8(2) . . . . ?
C10 C11 C12 C13 -0.5(3) . . . . ?
C9 C8 C13 C12 -0.2(3) . . . . ?
N2 C8 C13 C12 -177.3(2) . . . . ?
C11 C12 C13 C8 0.3(3) . . . . ?
C2 C7 N1 N2 0.4(2) . . . . ?
C6 C7 N1 N2 -179.6(2) . . . . ?
C7 N1 N2 C1 -0.6(2) . . . . ?
C7 N1 N2 C8 -179.02(18) . . . . ?
C2 C1 N2 N1 0.6(2) . . . . ?
P1 C1 N2 N1 -173.24(16) . . . . ?
C2 C1 N2 C8 178.8(2) . . . . ?
P1 C1 N2 C8 4.9(3) . . . . ?
C13 C8 N2 N1 67.0(3) . . . . ?
C9 C8 N2 N1 -110.1(2) . . . . ?
C13 C8 N2 C1 -111.2(3) . . . . ?
C9 C8 N2 C1 71.7(3) . . . . ?
C12 C11 O1 C14 -6.5(3) . . . . ?
C10 C11 O1 C14 174.2(2) . . . . ?
C15 O3 P1 O2 -74.9(3) . . . . ?
C15 O3 P1 O4 51.6(3) . . . . ?
C15 O3 P1 C1 162.5(2) . . . . ?
C16 O4 P1 O2 -39.2(2) . . . . ?
C16 O4 P1 O3 -167.5(2) . . . . ?
C16 O4 P1 C1 83.9(2) . . . . ?
N2 C1 P1 O2 172.86(19) . . . . ?
C2 C1 P1 O2 0.4(2) . . . . ?
N2 C1 P1 O3 -60.0(2) . . . . ?
C2 C1 P1 O3 127.5(2) . . . . ?
N2 C1 P1 O4 47.2(2) . . . . ?
C2 C1 P1 O4 -125.3(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C16 H16A O1 0.96 2.60 3.310(3) 131.0 1_565

_refine_diff_density_max         0.250
_refine_diff_density_min         -0.305
_refine_diff_density_rms         0.039

_shelxl_version_number           2012-9

