# Electronic Supplementary Material (ESI) for Catalysis Science and Technology
# This journal is © The Royal Society of Chemistry 2011


data_publication_text
_journal_name_full               Cat.Sci.Tech.
_journal_coden_cambridge         1486
#TrackingRef 'Compound_1.txt'

_publ_contact_author_name        'Saurav Bhardwaj'
_publ_contact_author_address     
;Department of Chemistry
University of Delhi
Delhi-110007
INDIA
;
_publ_contact_author_email       sauravbhardwaj20@gmail.com
loop_
_publ_author_address
;Department of Chemistry
University of Delhi
Delhi-110007
INDIA
;
loop_
_publ_author_name
M.Kidwai
S.Bhardwaj
A.Kumar
S.Mozumdar

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 761136'
#TrackingRef 'Compound_1.txt'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H22 N O5 P'
_chemical_formula_weight         363.34

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'
P P 0.1023 0.0942 '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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   ?

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

_cell_length_a                   22.1091(11)
_cell_length_b                   10.4184(3)
_cell_length_c                   18.2639(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 118.495(6)
_cell_angle_gamma                90.00
_cell_volume                     3697.3(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1536
_exptl_absorpt_coefficient_mu    0.176
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11650
_diffrn_reflns_av_R_equivalents  0.0186
_diffrn_reflns_av_sigmaI/netI    0.0380
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         32.45
_reflns_number_total             5850
_reflns_number_gt                3484
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.2000P)^2^+0.0000P] 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    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0035(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns         5850
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1878
_refine_ls_R_factor_gt           0.1463
_refine_ls_wR_factor_ref         0.4034
_refine_ls_wR_factor_gt          0.3717
_refine_ls_goodness_of_fit_ref   1.428
_refine_ls_restrained_S_all      1.428
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.03569(5) 0.25149(10) 0.01477(6) 0.0355(3) Uani 1 1 d . . .
N1 N -0.07580(18) 0.1528(3) -0.1097(2) 0.0373(7) Uani 1 1 d . . .
H1 H -0.0474 0.0904 -0.0996 0.045 Uiso 1 1 calc R . .
O1 O -0.1976(2) 0.4592(4) 0.0679(3) 0.0686(11) Uani 1 1 d . . .
O2 O -0.1955(3) 0.2784(4) 0.1414(3) 0.0649(11) Uani 1 1 d . . .
O3 O 0.05297(17) 0.3646(3) 0.07846(19) 0.0454(7) Uani 1 1 d . . .
O4 O 0.06093(18) 0.1241(3) 0.0507(2) 0.0498(8) Uani 1 1 d . . .
O5 O 0.06576(18) 0.3056(3) -0.0411(2) 0.0492(8) Uani 1 1 d . . .
C1 C -0.13822(19) 0.1516(4) -0.1827(2) 0.0327(7) Uani 1 1 d . . .
C7 C -0.0571(2) 0.2578(4) -0.0495(2) 0.0346(8) Uani 1 1 d . . .
H7 H -0.0682 0.3385 -0.0809 0.042 Uiso 1 1 calc R . .
C2 C -0.1577(2) 0.0385(4) -0.2299(2) 0.0395(9) Uani 1 1 d . . .
H2 H -0.1301 -0.0342 -0.2103 0.047 Uiso 1 1 calc R . .
C8 C -0.0945(2) 0.2584(4) 0.0022(2) 0.0341(8) Uani 1 1 d . . .
C13 C -0.1279(2) 0.3692(4) 0.0068(3) 0.0383(8) Uani 1 1 d . . .
H13 H -0.1278 0.4437 -0.0211 0.046 Uiso 1 1 calc R . .
C12 C -0.1614(2) 0.3647(5) 0.0543(3) 0.0443(10) Uani 1 1 d . . .
C3 C -0.2179(2) 0.0340(5) -0.3055(3) 0.0472(10) Uani 1 1 d . . .
H3 H -0.2302 -0.0415 -0.3365 0.057 Uiso 1 1 calc R . .
C6 C -0.1816(2) 0.2576(4) -0.2125(3) 0.0406(9) Uani 1 1 d . . .
H6 H -0.1703 0.3327 -0.1813 0.049 Uiso 1 1 calc R . .
C9 C -0.0946(3) 0.1491(5) 0.0459(3) 0.0534(12) Uani 1 1 d . . .
H9 H -0.0726 0.0755 0.0419 0.064 Uiso 1 1 calc R . .
C4 C -0.2592(3) 0.1395(6) -0.3348(3) 0.0545(12) Uani 1 1 d . . .
H4 H -0.2992 0.1362 -0.3858 0.065 Uiso 1 1 calc R . .
C5 C -0.2414(3) 0.2519(5) -0.2884(3) 0.0497(11) Uani 1 1 d . . .
H5 H -0.2697 0.3237 -0.3082 0.060 Uiso 1 1 calc R . .
C11 C -0.1606(3) 0.2559(5) 0.0971(3) 0.0472(10) Uani 1 1 d . . .
C14 C -0.2250(3) 0.4010(7) 0.1154(4) 0.0671(16) Uani 1 1 d . . .
H14A H -0.2151 0.4537 0.1637 0.080 Uiso 1 1 calc R . .
H14B H -0.2746 0.3933 0.0822 0.080 Uiso 1 1 calc R . .
C10 C -0.1269(3) 0.1468(5) 0.0960(4) 0.0604(14) Uani 1 1 d . . .
H10 H -0.1254 0.0747 0.1269 0.073 Uiso 1 1 calc R . .
C15 C 0.0685(4) 0.3402(7) 0.1641(3) 0.0745(19) Uani 1 1 d . . .
H15A H 0.0395 0.2713 0.1654 0.089 Uiso 1 1 calc R . .
H15B H 0.1161 0.3137 0.1965 0.089 Uiso 1 1 calc R . .
C16 C 0.0569(5) 0.4530(9) 0.1997(4) 0.096(3) Uani 1 1 d . . .
H16A H 0.0673 0.4359 0.2561 0.144 Uiso 1 1 calc R . .
H16B H 0.0096 0.4785 0.1679 0.144 Uiso 1 1 calc R . .
H16C H 0.0861 0.5208 0.1989 0.144 Uiso 1 1 calc R . .
C17 C 0.0721(3) 0.2149(5) -0.1031(3) 0.0500(11) Uani 1 1 d . . .
H17A H 0.0516 0.2499 -0.1591 0.060 Uiso 1 1 calc R . .
H17B H 0.0536 0.1302 -0.1038 0.060 Uiso 1 1 calc R . .
C18 C 0.1566(3) 0.2169(5) -0.0565(3) 0.0500(11) Uani 1 1 d . . .
H18A H 0.1725 0.1634 -0.0866 0.075 Uiso 1 1 calc R . .
H18B H 0.1743 0.1853 -0.0006 0.075 Uiso 1 1 calc R . .
H18C H 0.1723 0.3032 -0.0551 0.075 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 0.0336(5) 0.0335(5) 0.0374(5) 0.0021(4) 0.0153(4) 0.0008(4)
N1 0.0391(17) 0.0311(16) 0.0344(15) -0.0014(12) 0.0117(13) 0.0028(13)
O1 0.080(3) 0.055(2) 0.097(3) -0.002(2) 0.063(3) 0.011(2)
O2 0.077(3) 0.070(3) 0.074(3) -0.003(2) 0.056(2) -0.001(2)
O3 0.0476(17) 0.0448(17) 0.0397(15) -0.0040(13) 0.0176(13) -0.0049(14)
O4 0.0479(18) 0.0347(15) 0.0576(18) 0.0104(14) 0.0177(15) 0.0085(14)
O5 0.0524(19) 0.0457(19) 0.064(2) 0.0011(16) 0.0391(17) 0.0002(15)
C1 0.0335(17) 0.0352(18) 0.0335(16) 0.0011(14) 0.0194(14) 0.0005(14)
C7 0.0361(18) 0.0310(17) 0.0335(17) 0.0022(14) 0.0140(15) -0.0001(15)
C2 0.043(2) 0.036(2) 0.0401(18) -0.0024(15) 0.0200(16) -0.0002(16)
C8 0.0314(17) 0.0341(18) 0.0349(17) -0.0011(14) 0.0142(14) -0.0050(14)
C13 0.0380(19) 0.0336(19) 0.0409(18) 0.0017(15) 0.0168(16) -0.0003(16)
C12 0.042(2) 0.043(2) 0.047(2) -0.0102(18) 0.0208(18) -0.0002(18)
C3 0.040(2) 0.049(3) 0.048(2) -0.0128(19) 0.0172(18) -0.0066(19)
C6 0.038(2) 0.038(2) 0.0419(19) -0.0011(16) 0.0158(16) 0.0048(16)
C9 0.072(3) 0.037(2) 0.066(3) 0.012(2) 0.045(3) 0.009(2)
C4 0.040(2) 0.062(3) 0.046(2) -0.012(2) 0.0081(19) 0.001(2)
C5 0.037(2) 0.051(3) 0.051(2) 0.000(2) 0.0128(19) 0.0037(19)
C11 0.051(2) 0.053(3) 0.048(2) -0.0044(19) 0.032(2) -0.010(2)
C14 0.068(3) 0.090(4) 0.060(3) -0.009(3) 0.043(3) 0.004(3)
C10 0.083(4) 0.048(3) 0.073(3) 0.012(2) 0.056(3) 0.005(3)
C15 0.086(4) 0.079(4) 0.037(2) 0.005(3) 0.013(3) 0.023(4)
C16 0.136(7) 0.106(6) 0.059(3) 0.004(4) 0.057(4) 0.031(5)
C17 0.050(3) 0.050(3) 0.050(2) 0.000(2) 0.024(2) 0.000(2)
C18 0.050(3) 0.050(3) 0.050(2) 0.000(2) 0.024(2) 0.000(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 O4 1.468(3) . ?
P1 O5 1.565(3) . ?
P1 O3 1.569(3) . ?
P1 C7 1.815(4) . ?
N1 C1 1.388(5) . ?
N1 C7 1.464(5) . ?
O1 C12 1.364(6) . ?
O1 C14 1.412(7) . ?
O2 C11 1.379(6) . ?
O2 C14 1.410(8) . ?
O3 C15 1.456(6) . ?
O5 C17 1.531(6) . ?
C1 C6 1.391(6) . ?
C1 C2 1.401(6) . ?
C7 C8 1.524(6) . ?
C2 C3 1.389(6) . ?
C8 C9 1.391(6) . ?
C8 C13 1.395(6) . ?
C13 C12 1.383(6) . ?
C12 C11 1.372(7) . ?
C3 C4 1.365(8) . ?
C6 C5 1.387(7) . ?
C9 C10 1.405(7) . ?
C4 C5 1.389(7) . ?
C11 C10 1.365(8) . ?
C15 C16 1.423(10) . ?
C17 C18 1.643(7) . ?

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 P1 O5 115.4(2) . . ?
O4 P1 O3 116.2(2) . . ?
O5 P1 O3 100.62(19) . . ?
O4 P1 C7 113.18(19) . . ?
O5 P1 C7 105.41(19) . . ?
O3 P1 C7 104.63(18) . . ?
C1 N1 C7 121.6(3) . . ?
C12 O1 C14 105.3(4) . . ?
C11 O2 C14 104.8(4) . . ?
C15 O3 P1 121.0(4) . . ?
C17 O5 P1 118.5(3) . . ?
N1 C1 C6 123.5(4) . . ?
N1 C1 C2 118.2(4) . . ?
C6 C1 C2 118.3(4) . . ?
N1 C7 C8 115.2(3) . . ?
N1 C7 P1 106.6(3) . . ?
C8 C7 P1 112.3(3) . . ?
C3 C2 C1 120.5(4) . . ?
C9 C8 C13 119.8(4) . . ?
C9 C8 C7 120.1(4) . . ?
C13 C8 C7 120.1(3) . . ?
C12 C13 C8 117.8(4) . . ?
O1 C12 C11 110.0(4) . . ?
O1 C12 C13 128.7(4) . . ?
C11 C12 C13 121.4(4) . . ?
C4 C3 C2 120.5(4) . . ?
C5 C6 C1 120.5(4) . . ?
C8 C9 C10 121.8(5) . . ?
C3 C4 C5 119.9(4) . . ?
C6 C5 C4 120.2(5) . . ?
C10 C11 C12 122.6(4) . . ?
C10 C11 O2 127.8(5) . . ?
C12 C11 O2 109.6(5) . . ?
O2 C14 O1 109.3(4) . . ?
C11 C10 C9 116.5(5) . . ?
C16 C15 O3 110.2(5) . . ?
O5 C17 C18 95.3(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
O4 P1 O3 C15 -22.6(5) . . . . ?
O5 P1 O3 C15 -147.9(4) . . . . ?
C7 P1 O3 C15 102.9(5) . . . . ?
O4 P1 O5 C17 43.0(4) . . . . ?
O3 P1 O5 C17 168.8(3) . . . . ?
C7 P1 O5 C17 -82.6(4) . . . . ?
C7 N1 C1 C6 12.7(6) . . . . ?
C7 N1 C1 C2 -169.0(3) . . . . ?
C1 N1 C7 C8 74.0(5) . . . . ?
C1 N1 C7 P1 -160.7(3) . . . . ?
O4 P1 C7 N1 -52.1(3) . . . . ?
O5 P1 C7 N1 74.9(3) . . . . ?
O3 P1 C7 N1 -179.5(3) . . . . ?
O4 P1 C7 C8 75.0(3) . . . . ?
O5 P1 C7 C8 -158.0(3) . . . . ?
O3 P1 C7 C8 -52.4(3) . . . . ?
N1 C1 C2 C3 -176.7(4) . . . . ?
C6 C1 C2 C3 1.8(6) . . . . ?
N1 C7 C8 C9 52.9(5) . . . . ?
P1 C7 C8 C9 -69.4(5) . . . . ?
N1 C7 C8 C13 -128.1(4) . . . . ?
P1 C7 C8 C13 109.7(4) . . . . ?
C9 C8 C13 C12 -1.2(6) . . . . ?
C7 C8 C13 C12 179.7(4) . . . . ?
C14 O1 C12 C11 -5.1(6) . . . . ?
C14 O1 C12 C13 175.7(5) . . . . ?
C8 C13 C12 O1 -179.6(5) . . . . ?
C8 C13 C12 C11 1.4(6) . . . . ?
C1 C2 C3 C4 -0.5(7) . . . . ?
N1 C1 C6 C5 176.3(4) . . . . ?
C2 C1 C6 C5 -2.1(7) . . . . ?
C13 C8 C9 C10 -0.8(8) . . . . ?
C7 C8 C9 C10 178.3(5) . . . . ?
C2 C3 C4 C5 -0.7(8) . . . . ?
C1 C6 C5 C4 1.0(8) . . . . ?
C3 C4 C5 C6 0.4(9) . . . . ?
O1 C12 C11 C10 -178.8(6) . . . . ?
C13 C12 C11 C10 0.4(8) . . . . ?
O1 C12 C11 O2 -1.3(6) . . . . ?
C13 C12 C11 O2 177.9(4) . . . . ?
C14 O2 C11 C10 -175.5(6) . . . . ?
C14 O2 C11 C12 7.2(6) . . . . ?
C11 O2 C14 O1 -10.4(6) . . . . ?
C12 O1 C14 O2 9.7(6) . . . . ?
C12 C11 C10 C9 -2.3(9) . . . . ?
O2 C11 C10 C9 -179.3(6) . . . . ?
C8 C9 C10 C11 2.5(9) . . . . ?
P1 O3 C15 C16 -158.2(6) . . . . ?
P1 O5 C17 C18 -113.9(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.877
_diffrn_reflns_theta_full        32.45
_diffrn_measured_fraction_theta_full 0.877
_refine_diff_density_max         2.554
_refine_diff_density_min         -3.453
_refine_diff_density_rms         0.189