# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               'RSC Advances'
_journal_coden_cambridge         1500
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
loop_
_publ_author_name
_publ_author_address
B.Duda
;School of Engineering and Science, Jacobs University Bremen,
Campus Ring 1, 28759 Bremen Germany.
;
S.N.Tverdomed
;School of Engineering and Science, Jacobs University Bremen,
Campus Ring 1, 28759 Bremen Germany.
Department of Organic Chemistry, St. Petersburg Institute of
Technology (Technical University), Moskovskii pr. 26, 190013
St. Petersburg, Russia.
;
G.-V.Roschenthaler
;School of Engineering and Science, Jacobs University Bremen,
Campus Ring 1, 28759 Bremen Germany.
Department of Organic Chemistry, St. Petersburg Institute of
Technology (Technical University), Moskovskii pr. 26, 190013
St. Petersburg, Russia.
;
_publ_contact_author_address     
;School of Engineering and Science, Jacobs University Bremen,
Campus Ring 1, 28759 Bremen Germany.
Department of Organic Chemistry, St. Petersburg Institute of
Technology (Technical University), Moskovskii pr. 26, 190013
St. Petersburg, Russia.
;
_publ_contact_author_email       s.tverdomed@jacosb-university.de
_publ_contact_author_fax         '+49 421 200 3229'
_publ_contact_author_phone       '+49 421 200 3138'
_publ_contact_author_name        'Sergey N. Tverdomed'

data_try
_database_code_depnum_ccdc_archive 'CCDC 884142'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H19 F3 N O5 P'
_chemical_formula_weight         393.29

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'
F F 0.0171 0.0103 '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           Triclinic
_symmetry_space_group_name_H-M   P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4669(6)
_cell_length_b                   9.0018(6)
_cell_length_c                   12.9910(11)
_cell_angle_alpha                93.708(5)
_cell_angle_beta                 95.044(6)
_cell_angle_gamma                93.142(5)
_cell_volume                     866.39(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4001
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      24.30

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             408
_exptl_absorpt_coefficient_mu    0.218
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9180
_exptl_absorpt_correction_T_max  0.9892
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(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  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39542
_diffrn_reflns_av_R_equivalents  0.0940
_diffrn_reflns_av_sigmaI/netI    0.0494
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.45
_diffrn_reflns_theta_max         26.37
_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.988
_reflns_number_total             3497
_reflns_number_gt                2478
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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^)+(0.0500P)^2^+0.3600P] 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    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3497
_refine_ls_number_parameters     311
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0426
_refine_ls_wR_factor_ref         0.1118
_refine_ls_wR_factor_gt          0.0985
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_restrained_S_all      1.024
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.493
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.057

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 0.2246(3) 0.2733(2) 0.31977(18) 0.0225(5) Uani 1 1 d . . .
C2 C 0.1304(3) 0.1395(2) 0.27468(18) 0.0221(5) Uani 1 1 d . . .
C3 C 0.3600(3) 0.1324(2) 0.57816(17) 0.0204(5) Uani 1 1 d . . .
H1C3 H 0.421(3) 0.215(3) 0.6106(19) 0.025(6) Uiso 1 1 d . . .
C4 C 0.1928(3) 0.0115(2) 0.42086(17) 0.0195(5) Uani 1 1 d . . .
C5 C 0.2833(3) 0.1396(2) 0.47492(17) 0.0204(5) Uani 1 1 d . . .
C6 C 0.3002(3) 0.2687(2) 0.42056(18) 0.0224(5) Uani 1 1 d . . .
H2C6 H 0.367(3) 0.353(3) 0.4518(18) 0.019(6) Uiso 1 1 d . . .
C7 C 0.1827(3) -0.1246(2) 0.47045(17) 0.0205(5) Uani 1 1 d . . .
H2C7 H 0.126(3) -0.208(3) 0.432(2) 0.032(7) Uiso 1 1 d . . .
C8 C 0.2610(3) -0.1304(2) 0.56859(17) 0.0200(5) Uani 1 1 d . . .
C9 C 0.3495(3) 0.0005(2) 0.62427(17) 0.0200(5) Uani 1 1 d . . .
C10 C 0.0422(3) 0.1207(3) 0.16463(18) 0.0267(5) Uani 1 1 d . . .
C1P1 C 0.0780(4) 0.6438(3) 0.1736(2) 0.0359(6) Uani 1 1 d . . .
H311 H 0.180(4) 0.644(3) 0.121(2) 0.049(8) Uiso 1 1 d . . .
H211 H 0.095(4) 0.728(3) 0.230(2) 0.045(8) Uiso 1 1 d . . .
C1P2 C 0.5166(3) 0.3373(3) 0.1462(2) 0.0282(6) Uani 1 1 d . . .
H212 H 0.530(3) 0.263(3) 0.1948(19) 0.025(6) Uiso 1 1 d . . .
H112 H 0.606(4) 0.418(3) 0.170(2) 0.039(8) Uiso 1 1 d . . .
C1O3 C 0.1935(4) -0.3914(3) 0.5700(2) 0.0271(5) Uani 1 1 d . . .
H3O3 H 0.250(3) -0.409(3) 0.509(2) 0.028(7) Uiso 1 1 d . . .
H2O3 H 0.060(4) -0.388(3) 0.553(2) 0.034(7) Uiso 1 1 d . . .
H1O3 H 0.228(3) -0.466(3) 0.616(2) 0.033(7) Uiso 1 1 d . . .
C1O4 C 0.4988(4) 0.1061(3) 0.7825(2) 0.0293(6) Uani 1 1 d . . .
H3O4 H 0.602(4) 0.153(3) 0.751(2) 0.034(7) Uiso 1 1 d . . .
H2O4 H 0.400(3) 0.176(3) 0.7917(18) 0.024(6) Uiso 1 1 d . . .
H1O4 H 0.541(4) 0.071(3) 0.847(2) 0.042(8) Uiso 1 1 d . . .
C2P1 C -0.1007(5) 0.6373(4) 0.1157(3) 0.0496(8) Uani 1 1 d . . .
H221 H -0.109(4) 0.723(4) 0.078(2) 0.058(9) Uiso 1 1 d . . .
H121 H -0.191(5) 0.635(4) 0.173(3) 0.087(13) Uiso 1 1 d . . .
H321 H -0.118(5) 0.542(5) 0.069(3) 0.091(13) Uiso 1 1 d . . .
C2P2 C 0.5348(4) 0.2795(3) 0.0375(2) 0.0332(6) Uani 1 1 d . . .
H322 H 0.652(4) 0.233(3) 0.033(2) 0.049(8) Uiso 1 1 d . . .
H222 H 0.443(4) 0.206(3) 0.013(2) 0.043(8) Uiso 1 1 d . . .
H122 H 0.531(4) 0.359(3) -0.009(2) 0.049(8) Uiso 1 1 d . . .
N1 N 0.1161(2) 0.01401(19) 0.32192(14) 0.0218(4) Uani 1 1 d . . .
O1P O 0.0901(2) 0.51040(18) 0.23332(13) 0.0325(4) Uani 1 1 d . . .
O2P O 0.3393(2) 0.39908(17) 0.14993(12) 0.0254(4) Uani 1 1 d . . .
O3 O 0.2664(2) -0.25392(16) 0.62339(12) 0.0239(4) Uani 1 1 d . . .
O3P O 0.4087(2) 0.54223(17) 0.32707(13) 0.0316(4) Uani 1 1 d . . .
O4 O 0.4221(2) -0.02320(16) 0.72094(12) 0.0254(4) Uani 1 1 d . . .
F1 F 0.1620(2) 0.07565(17) 0.09829(11) 0.0398(4) Uani 1 1 d . . .
F2 F -0.0203(2) 0.24599(16) 0.12945(12) 0.0391(4) Uani 1 1 d . . .
F3 F -0.0948(2) 0.01908(16) 0.15263(11) 0.0385(4) Uani 1 1 d . . .
P P 0.27682(9) 0.44430(6) 0.25993(5) 0.02588(18) Uani 1 1 d . . .

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
C1 0.0225(12) 0.0204(11) 0.0259(13) 0.0014(9) 0.0061(10) 0.0066(9)
C2 0.0192(12) 0.0239(12) 0.0239(12) 0.0011(9) 0.0030(9) 0.0064(9)
C3 0.0231(12) 0.0167(11) 0.0211(12) -0.0025(9) 0.0032(9) 0.0019(9)
C4 0.0174(11) 0.0206(11) 0.0212(12) 0.0008(9) 0.0036(9) 0.0043(9)
C5 0.0184(11) 0.0192(11) 0.0245(12) -0.0003(9) 0.0053(9) 0.0063(9)
C6 0.0235(12) 0.0183(12) 0.0254(13) -0.0022(10) 0.0034(10) 0.0049(10)
C7 0.0214(11) 0.0174(11) 0.0226(12) -0.0005(9) 0.0027(9) 0.0011(9)
C8 0.0198(11) 0.0176(11) 0.0234(12) 0.0004(9) 0.0049(9) 0.0037(9)
C9 0.0204(11) 0.0222(11) 0.0180(11) -0.0009(9) 0.0043(9) 0.0055(9)
C10 0.0266(13) 0.0264(12) 0.0272(13) 0.0066(10) -0.0002(10) 0.0019(10)
C1P1 0.0427(16) 0.0232(13) 0.0411(16) 0.0068(12) -0.0056(13) 0.0055(11)
C1P2 0.0253(13) 0.0299(13) 0.0290(14) 0.0026(11) -0.0009(11) 0.0039(11)
C1O3 0.0344(15) 0.0180(12) 0.0281(14) 0.0005(10) 0.0009(12) -0.0014(10)
C1O4 0.0384(16) 0.0246(13) 0.0232(13) -0.0045(10) -0.0037(12) 0.0046(12)
C2P1 0.051(2) 0.0387(18) 0.058(2) 0.0150(16) -0.0116(17) 0.0081(15)
C2P2 0.0302(15) 0.0414(16) 0.0282(15) 0.0013(12) 0.0025(12) 0.0071(13)
N1 0.0219(10) 0.0214(10) 0.0223(10) 0.0019(8) 0.0017(8) 0.0028(8)
O1P 0.0399(10) 0.0253(9) 0.0355(10) 0.0096(7) 0.0086(8) 0.0130(8)
O2P 0.0297(9) 0.0243(8) 0.0229(9) 0.0031(7) 0.0034(7) 0.0058(7)
O3 0.0319(9) 0.0156(8) 0.0236(9) 0.0017(6) -0.0007(7) -0.0005(7)
O3P 0.0479(11) 0.0187(8) 0.0277(9) 0.0026(7) 0.0016(8) 0.0000(7)
O4 0.0343(9) 0.0202(8) 0.0207(9) 0.0002(6) -0.0025(7) 0.0022(7)
F1 0.0392(9) 0.0589(10) 0.0217(8) -0.0010(7) 0.0030(6) 0.0104(7)
F2 0.0447(9) 0.0329(8) 0.0380(9) 0.0094(7) -0.0125(7) 0.0061(7)
F3 0.0376(9) 0.0427(9) 0.0318(8) 0.0077(7) -0.0097(7) -0.0129(7)
P 0.0355(4) 0.0187(3) 0.0244(3) 0.0032(2) 0.0040(3) 0.0059(3)

_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 C6 1.383(3) . ?
C1 C2 1.425(3) . ?
C1 P 1.808(2) . ?
C2 N1 1.324(3) . ?
C2 C10 1.516(3) . ?
C3 C9 1.366(3) . ?
C3 C5 1.418(3) . ?
C4 N1 1.363(3) . ?
C4 C5 1.416(3) . ?
C4 C7 1.422(3) . ?
C5 C6 1.404(3) . ?
C7 C8 1.361(3) . ?
C8 O3 1.359(3) . ?
C8 C9 1.438(3) . ?
C9 O4 1.358(3) . ?
C10 F3 1.326(3) . ?
C10 F2 1.336(3) . ?
C10 F1 1.355(3) . ?
C1P1 C2P1 1.469(4) . ?
C1P1 O1P 1.474(3) . ?
C1P2 O2P 1.467(3) . ?
C1P2 C2P2 1.493(4) . ?
C1O3 O3 1.434(3) . ?
C1O4 O4 1.432(3) . ?
O1P P 1.5655(18) . ?
O2P P 1.5775(17) . ?
O3P P 1.4704(18) . ?

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
C6 C1 C2 116.1(2) . . ?
C6 C1 P 114.73(17) . . ?
C2 C1 P 128.88(18) . . ?
N1 C2 C1 124.3(2) . . ?
N1 C2 C10 111.44(19) . . ?
C1 C2 C10 124.2(2) . . ?
C9 C3 C5 119.6(2) . . ?
N1 C4 C5 121.96(19) . . ?
N1 C4 C7 118.68(19) . . ?
C5 C4 C7 119.4(2) . . ?
C6 C5 C4 117.3(2) . . ?
C6 C5 C3 122.5(2) . . ?
C4 C5 C3 120.14(19) . . ?
C1 C6 C5 121.6(2) . . ?
C8 C7 C4 119.7(2) . . ?
O3 C8 C7 125.68(19) . . ?
O3 C8 C9 113.43(19) . . ?
C7 C8 C9 120.9(2) . . ?
O4 C9 C3 125.7(2) . . ?
O4 C9 C8 114.01(18) . . ?
C3 C9 C8 120.3(2) . . ?
F3 C10 F2 106.60(19) . . ?
F3 C10 F1 106.39(19) . . ?
F2 C10 F1 105.89(18) . . ?
F3 C10 C2 112.98(19) . . ?
F2 C10 C2 113.90(19) . . ?
F1 C10 C2 110.55(19) . . ?
C2P1 C1P1 O1P 108.3(2) . . ?
O2P C1P2 C2P2 108.4(2) . . ?
C2 N1 C4 118.64(19) . . ?
C1P1 O1P P 120.24(16) . . ?
C1P2 O2P P 117.62(14) . . ?
C8 O3 C1O3 116.63(18) . . ?
C9 O4 C1O4 116.06(18) . . ?
O3P P O1P 115.53(10) . . ?
O3P P O2P 114.29(10) . . ?
O1P P O2P 103.11(9) . . ?
O3P P C1 111.07(10) . . ?
O1P P C1 104.89(10) . . ?
O2P P C1 107.08(9) . . ?