# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_shelxl
#TrackingRef '12896_web_deposit_cif_file_0_yancai_1343375833.shelxl.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H18 N O5 P'
_chemical_formula_weight         323.27

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

_symmetry_cell_setting           ORTHORHOMBIC
_symmetry_space_group_name_H-M   Pnma

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

_cell_length_a                   14.554(3)
_cell_length_b                   12.849(3)
_cell_length_c                   8.6466(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1617.0(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4258
_cell_measurement_theta_min      2.7992
_cell_measurement_theta_max      27.8505

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9626
_exptl_absorpt_correction_T_max  0.9811
_exptl_absorpt_process_details   crystalclear

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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       '\w 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            15501
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_av_sigmaI/netI    0.0222
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.80
_diffrn_reflns_theta_max         27.86
_reflns_number_total             2001
_reflns_number_gt                1613
_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 F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.1011P)^2^+0.1040P] where P=(Fo^2^+2Fc^2^)/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     SHELXL
_refine_ls_extinction_coef       0.072(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         2001
_refine_ls_number_parameters     112
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.1570
_refine_ls_wR_factor_gt          0.1450
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_restrained_S_all      1.097
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

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 -0.03938(4) 0.2500 0.32926(7) 0.0506(3) Uani 1 2 d S . .
O1 O 0.18538(11) 0.07208(9) 0.32871(15) 0.0607(4) Uani 1 1 d . . .
O2 O 0.01176(13) 0.2500 0.47525(19) 0.0705(6) Uani 1 2 d S . .
O3 O -0.10873(9) 0.15789(11) 0.30472(17) 0.0666(5) Uani 1 1 d . . .
N1 N 0.17581(12) 0.2500 0.2917(2) 0.0389(5) Uani 1 2 d S . .
C1 C 0.35548(14) 0.19647(18) 0.7237(2) 0.0652(6) Uani 1 1 d . . .
H1 H 0.3885 0.1611 0.7992 0.078 Uiso 1 1 calc R . .
C2 C 0.30708(13) 0.13999(16) 0.6130(2) 0.0560(5) Uani 1 1 d . . .
H2 H 0.3067 0.0676 0.6135 0.067 Uiso 1 1 calc R . .
C3 C 0.25955(10) 0.19614(12) 0.50214(16) 0.0413(4) Uani 1 1 d . . .
C4 C 0.20434(11) 0.15996(12) 0.36806(19) 0.0419(4) Uani 1 1 d . . .
C5 C 0.12165(16) 0.2500 0.1532(2) 0.0455(6) Uani 1 2 d S . .
C6 C 0.1771(2) 0.2500 0.0073(3) 0.0777(10) Uani 1 2 d S . .
H6A H 0.1372 0.2395 -0.0797 0.117 Uiso 0.50 1 calc PR . .
H6B H 0.2217 0.1949 0.0113 0.117 Uiso 0.50 1 calc PR . .
H6C H 0.2081 0.3156 -0.0032 0.117 Uiso 0.50 1 calc PR . .
C7 C 0.03062(16) 0.2500 0.1607(3) 0.0487(6) Uani 1 2 d S . .
H7 H -0.0003 0.2500 0.0665 0.058 Uiso 1 2 calc SR . .
C8 C -0.0840(3) 0.0552(2) 0.3528(3) 0.1019(9) Uani 1 1 d DU . .
H8A H -0.0252 0.0583 0.4053 0.122 Uiso 1 1 calc R . .
H8B H -0.1292 0.0307 0.4268 0.122 Uiso 1 1 calc R . .
C9 C -0.0778(3) -0.0180(3) 0.2297(4) 0.1269(13) Uani 1 1 d DU . .
H9A H -0.1349 -0.0194 0.1740 0.190 Uiso 1 1 calc R . .
H9B H -0.0653 -0.0858 0.2710 0.190 Uiso 1 1 calc R . .
H9C H -0.0291 0.0020 0.1609 0.190 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
P1 0.0308(4) 0.0752(5) 0.0458(4) 0.000 -0.0013(2) 0.000
O1 0.0715(9) 0.0443(7) 0.0662(8) -0.0068(6) -0.0042(6) -0.0053(6)
O2 0.0443(10) 0.1280(18) 0.0393(9) 0.000 0.0011(8) 0.000
O3 0.0437(7) 0.0748(10) 0.0814(10) 0.0118(7) -0.0054(6) -0.0077(6)
N1 0.0335(9) 0.0442(10) 0.0392(9) 0.000 0.0000(7) 0.000
C1 0.0554(11) 0.1009(15) 0.0394(9) 0.0086(9) -0.0046(8) 0.0091(10)
C2 0.0593(11) 0.0602(10) 0.0486(9) 0.0095(8) -0.0019(8) 0.0091(9)
C3 0.0379(8) 0.0472(9) 0.0388(8) 0.0017(6) 0.0017(6) 0.0019(6)
C4 0.0396(8) 0.0418(9) 0.0443(9) -0.0008(6) 0.0038(6) -0.0004(6)
C5 0.0412(12) 0.0589(14) 0.0364(11) 0.000 0.0001(9) 0.000
C6 0.0573(17) 0.133(3) 0.0426(14) 0.000 0.0077(12) 0.000
C7 0.0400(12) 0.0693(16) 0.0368(11) 0.000 -0.0070(9) 0.000
C8 0.120(2) 0.0823(19) 0.1033(18) 0.0310(15) -0.0204(18) -0.0122(18)
C9 0.137(3) 0.098(2) 0.146(3) -0.003(2) 0.003(2) 0.035(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 1.4654(19) . ?
P1 O3 1.5699(14) 8_565 ?
P1 O3 1.5699(14) . ?
P1 C7 1.779(2) . ?
O1 C4 1.2112(19) . ?
O3 C8 1.429(3) . ?
N1 C4 1.3953(18) . ?
N1 C4 1.3953(18) 8_565 ?
N1 C5 1.434(3) . ?
C1 C1 1.376(5) 8_565 ?
C1 C2 1.392(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.385(2) . ?
C2 H2 0.9300 . ?
C3 C3 1.384(3) 8_565 ?
C3 C4 1.485(2) . ?
C5 C7 1.326(3) . ?
C5 C6 1.498(3) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7 0.9300 . ?
C8 C9 1.423(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 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
O2 P1 O3 116.30(7) . 8_565 ?
O2 P1 O3 116.29(7) . . ?
O3 P1 O3 97.86(11) 8_565 . ?
O2 P1 C7 114.53(11) . . ?
O3 P1 C7 104.92(8) 8_565 . ?
O3 P1 C7 104.92(8) . . ?
C8 O3 P1 119.65(17) . . ?
C4 N1 C4 112.03(17) . 8_565 ?
C4 N1 C5 123.98(9) . . ?
C4 N1 C5 123.97(9) 8_565 . ?
C1 C1 C2 121.42(12) 8_565 . ?
C1 C1 H1 119.3 8_565 . ?
C2 C1 H1 119.3 . . ?
C3 C2 C1 117.18(19) . . ?
C3 C2 H2 121.4 . . ?
C1 C2 H2 121.4 . . ?
C3 C3 C2 121.40(11) 8_565 . ?
C3 C3 C4 108.24(9) 8_565 . ?
C2 C3 C4 130.35(16) . . ?
O1 C4 N1 124.91(16) . . ?
O1 C4 C3 129.38(16) . . ?
N1 C4 C3 105.71(13) . . ?
C7 C5 N1 120.56(19) . . ?
C7 C5 C6 125.4(2) . . ?
N1 C5 C6 114.0(2) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 P1 127.74(17) . . ?
C5 C7 H7 116.1 . . ?
P1 C7 H7 116.1 . . ?
C9 C8 O3 114.1(2) . . ?
C9 C8 H8A 108.7 . . ?
O3 C8 H8A 108.7 . . ?
C9 C8 H8B 108.7 . . ?
O3 C8 H8B 108.7 . . ?
H8A C8 H8B 107.6 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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 C8 -39.9(2) . . . . ?
O3 P1 O3 C8 -164.46(17) 8_565 . . . ?
C7 P1 O3 C8 87.7(2) . . . . ?
C1 C1 C2 C3 0.5(2) 8_565 . . . ?
C1 C2 C3 C3 -0.5(2) . . . 8_565 ?
C1 C2 C3 C4 178.12(16) . . . . ?
C4 N1 C4 O1 176.97(11) 8_565 . . . ?
C5 N1 C4 O1 -1.6(3) . . . . ?
C4 N1 C4 C3 -2.5(2) 8_565 . . . ?
C5 N1 C4 C3 178.91(17) . . . . ?
C3 C3 C4 O1 -177.98(17) 8_565 . . . ?
C2 C3 C4 O1 3.2(3) . . . . ?
C3 C3 C4 N1 1.49(14) 8_565 . . . ?
C2 C3 C4 N1 -177.29(16) . . . . ?
C4 N1 C5 C7 89.20(17) . . . . ?
C4 N1 C5 C7 -89.20(17) 8_565 . . . ?
C4 N1 C5 C6 -90.80(17) . . . . ?
C4 N1 C5 C6 90.80(17) 8_565 . . . ?
N1 C5 C7 P1 0.0 . . . . ?
C6 C5 C7 P1 180.0 . . . . ?
O2 P1 C7 C5 0.0 . . . . ?
O3 P1 C7 C5 128.72(6) 8_565 . . . ?
O3 P1 C7 C5 -128.72(6) . . . . ?
P1 O3 C8 C9 -116.7(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.86
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.042


_database_code_depnum_ccdc_archive 'CCDC 893994'