# Supplementary Material (ESI) for Perkin Transactions
# This journal is © The Royal Society of Chemistry 2001


data_global 
_journal_coden_Cambridge          207        
_publ_contact_author              'Dr Shizheng Zhu'
_publ_contact_author_address     
;
Dr Shizheng Zhu
Shanghai Institute of Organic Chemistry
Chinese Academy Sciences
354 Fenglin Lu
Shanghai
200032
CHINA      
;
_publ_contact_author_phone        '086 21 64163300 3525'
_publ_contact_author_fax          '086 21 64166128'
_publ_contact_author_email        'zhusz@pub.sioc.ac.cn'
_publ_requested_journal           'Perkin Transactions 1'
_publ_requested_coeditor_name     ?

_publ_contact_letter
;
Please consider this CIF submission for publication in "J. C. S. Perkin
Trans.".
S. Z. Zhu
;

#=============================================================================

# 3. TITLE AND AUTHOR LIST

_publ_section_title
;
Reactions of N-benzyl pyridinium or isoquinolinium ylide with ethyl 3-fluoro-
alkyl-3-fluoro-acrylates to fluoroalkyl substituted indolizine derivatives
;

loop_
_publ_author_name
_publ_author_address
'Peng, Weiming'
;     Shanghai Institute of Organic Chemistry
Chinese Academy of Sciences
354 Fenglin Lu
Shanghai
200032 P. R. China
;
'Zhu, Shizheng'
;     Shanghai Institute of Organic Chemistry
Chinese Academy of Sciences
354 Fenglin Lu
Shanghai
200032 P. R. China
;

data_C22H16FNO3 

_database_code_CSD	163149


_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
? 
; 
_chemical_name_common             ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
'C22 H16 F N O3' 
_chemical_formula_weight          361.36 

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' 

_symmetry_cell_setting            MONOCLINIC 
_symmetry_space_group_name_H-M    C2/C 

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                    20.375(4) 
_cell_length_b                    11.151(2) 
_cell_length_c                    16.522(4) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  103.550(10) 
_cell_angle_gamma                 90.00 
_cell_volume                      3649.3(13) 
_cell_formula_units_Z             8 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     25 
_cell_measurement_theta_min       5.0 
_cell_measurement_theta_max       12.5 

_exptl_crystal_description        block 
_exptl_crystal_colour             colorless 
_exptl_crystal_size_max           0.400 
_exptl_crystal_size_mid           0.200 
_exptl_crystal_size_min           0.133 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.315 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              1504 
_exptl_absorpt_coefficient_mu     0.095 
_exptl_absorpt_correction_type    empirical 
_exptl_absorpt_correction_T_min   0.933 
_exptl_absorpt_correction_T_max   0.958 

_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   Bruker P4 
_diffrn_measurement_method        theta/2theta 
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          3 
_diffrn_standards_interval_count  97 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         no 
_diffrn_reflns_number             5026 
_diffrn_reflns_av_R_equivalents   0.0473 
_diffrn_reflns_av_sigmaI/netI     0.1319 
_diffrn_reflns_limit_h_min        -1 
_diffrn_reflns_limit_h_max        26 
_diffrn_reflns_limit_k_min        -14 
_diffrn_reflns_limit_k_max        1 
_diffrn_reflns_limit_l_min        -21 
_diffrn_reflns_limit_l_max        21 
_diffrn_reflns_theta_min          2.06 
_diffrn_reflns_theta_max          27.51 
_reflns_number_total              4199 
_reflns_number_gt                 1565 
_reflns_threshold_expression      >2sigma(I) 

_computing_data_collection        ? 
_computing_cell_refinement        ? 
_computing_data_reduction         ? 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_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 w=1/[\s^2^(Fo^2^)+(0.0508P)^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        0.0021(3) 
_refine_ls_extinction_expression 
'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' 
_refine_ls_number_reflns          4199 
_refine_ls_number_parameters      309 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.2076 
_refine_ls_R_factor_gt            0.0652 
_refine_ls_wR_factor_ref          0.1502 
_refine_ls_wR_factor_gt           0.1116 
_refine_ls_goodness_of_fit_ref    0.959 
_refine_ls_restrained_S_all       0.959 
_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_calc_flag 
_atom_site_refinement_flags 
_atom_site_disorder_assembly 
_atom_site_disorder_group 
C1 C 0.20206(15) 0.4037(3) 0.15497(17) 0.0435(8) Uani 1 d . . . 
C2 C 0.14867(14) 0.4867(3) 0.13400(17) 0.0468(8) Uani 1 d . . . 
C3 C 0.15137(14) 0.5422(3) 0.05982(18) 0.0473(8) Uani 1 d . . . 
N N 0.20523(12) 0.4927(2) 0.03525(14) 0.0450(6) Uani 1 d . . . 
C4 C 0.22744(17) 0.5179(3) -0.0372(2) 0.0538(9) Uani 1 d . . . 
C5 C 0.28123(17) 0.4612(3) -0.0509(2) 0.0551(9) Uani 1 d . . . 
C6 C 0.31802(16) 0.3752(3) 0.00611(18) 0.0484(8) Uani 1 d . . . 
C7 C 0.37599(18) 0.3201(3) -0.0074(2) 0.0580(9) Uani 1 d . . . 
C8 C 0.41333(19) 0.2423(3) 0.0496(2) 0.0618(10) Uani 1 d . . . 
C9 C 0.3930(2) 0.2168(3) 0.1218(2) 0.0650(11) Uani 1 d . . . 
C10 C 0.33516(18) 0.2686(3) 0.1368(2) 0.0572(10) Uani 1 d . . . 
C11 C 0.29697(15) 0.3485(3) 0.07950(18) 0.0458(8) Uani 1 d . . . 
C12 C 0.23746(14) 0.4079(3) 0.09364(17) 0.0428(8) Uani 1 d . . . 
C13 C 0.21449(17) 0.3246(3) 0.22923(19) 0.0509(8) Uani 1 d . . . 
O1 O 0.25855(12) 0.3388(2) 0.29059(13) 0.0813(8) Uani 1 d . . . 
O2 O 0.17019(11) 0.2359(2) 0.21980(12) 0.0598(7) Uani 1 d . . . 
C14 C 0.1727(2) 0.1580(4) 0.2915(2) 0.0761(12) Uani 1 d . . . 
C15 C 0.1192(3) 0.0669(5) 0.2653(3) 0.0864(14) Uani 1 d . . . 
C16 C 0.10211(17) 0.5111(3) 0.1850(2) 0.0620(10) Uani 1 d . . . 
O3 O 0.10633(12) 0.4656(2) 0.25364(14) 0.0782(8) Uani 1 d . . . 
F F 0.05314(11) 0.5858(2) 0.15687(13) 0.0971(8) Uani 1 d . . . 
C17 C 0.11036(15) 0.6394(3) 0.01144(19) 0.0486(8) Uani 1 d . . . 
C18 C 0.1149(2) 0.7542(4) 0.0426(3) 0.0737(11) Uani 1 d . . . 
C19 C 0.0766(2) 0.8455(4) -0.0010(3) 0.0842(13) Uani 1 d . . . 
C20 C 0.0342(2) 0.8247(4) -0.0764(3) 0.0715(11) Uani 1 d . . . 
C21 C 0.0292(2) 0.7110(4) -0.1072(2) 0.0734(12) Uani 1 d . . . 
C22 C 0.06733(19) 0.6193(4) -0.0640(2) 0.0632(10) Uani 1 d . . . 
H4 H 0.2019(15) 0.583(3) -0.0705(17) 0.068(10) Uiso 1 d . . . 
H5 H 0.3004(13) 0.478(2) -0.1009(17) 0.055(9) Uiso 1 d . . . 
H7 H 0.3895(14) 0.340(3) -0.0576(17) 0.055(9) Uiso 1 d . . . 
H8 H 0.4539(16) 0.206(3) 0.0410(17) 0.062(10) Uiso 1 d . . . 
H9 H 0.4193(18) 0.172(3) 0.160(2) 0.091(14) Uiso 1 d . . . 
H10 H 0.3247(15) 0.251(3) 0.189(2) 0.064(10) Uiso 1 d . . . 
H14A H 0.1633(19) 0.220(3) 0.342(2) 0.108(14) Uiso 1 d . . . 
H14B H 0.2188(19) 0.126(3) 0.306(2) 0.096(14) Uiso 1 d . . . 
H15A H 0.076(2) 0.105(4) 0.242(2) 0.111(16) Uiso 1 d . . . 
H15B H 0.122(2) 0.011(4) 0.217(3) 0.133(19) Uiso 1 d . . . 
H15C H 0.1160(17) 0.012(3) 0.314(2) 0.094(12) Uiso 1 d . . . 
H18 H 0.1434(18) 0.763(3) 0.098(2) 0.081(11) Uiso 1 d . . . 
H19 H 0.081(2) 0.926(4) 0.018(2) 0.113(16) Uiso 1 d . . . 
H20 H 0.007(2) 0.891(3) -0.107(2) 0.111(15) Uiso 1 d . . . 
H21 H 0.0028(19) 0.689(3) -0.159(2) 0.101(14) Uiso 1 d . . . 
H22 H 0.0632(12) 0.544(2) -0.0891(15) 0.039(8) Uiso 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 0.0454(19) 0.048(2) 0.0352(16) 0.0000(16) 0.0047(15) -0.0007(17) 
C2 0.0427(18) 0.059(2) 0.0375(17) -0.0014(17) 0.0074(15) 0.0029(18) 
C3 0.0380(19) 0.050(2) 0.0495(19) -0.0021(17) 0.0010(15) -0.0015(16) 
N 0.0434(15) 0.0483(16) 0.0420(14) 0.0048(13) 0.0078(12) 0.0007(14) 
C4 0.046(2) 0.061(2) 0.052(2) 0.0089(19) 0.0065(17) -0.003(2) 
C5 0.047(2) 0.070(2) 0.049(2) 0.009(2) 0.0129(18) -0.002(2) 
C6 0.045(2) 0.053(2) 0.0451(19) -0.0011(17) 0.0062(16) -0.0046(18) 
C7 0.057(2) 0.062(2) 0.057(2) 0.000(2) 0.0188(19) -0.005(2) 
C8 0.053(2) 0.061(2) 0.076(3) 0.002(2) 0.023(2) 0.010(2) 
C9 0.068(3) 0.059(2) 0.069(3) 0.010(2) 0.017(2) 0.013(2) 
C10 0.064(3) 0.053(2) 0.057(2) 0.0021(19) 0.020(2) 0.0073(19) 
C11 0.048(2) 0.0413(19) 0.0444(18) -0.0009(16) 0.0031(16) 0.0011(17) 
C12 0.0464(19) 0.0409(19) 0.0375(16) 0.0031(15) 0.0028(15) 0.0041(16) 
C13 0.050(2) 0.063(2) 0.0397(19) -0.0018(18) 0.0107(17) 0.009(2) 
O1 0.0763(17) 0.108(2) 0.0483(13) 0.0095(14) -0.0081(13) -0.0059(16) 
O2 0.0676(16) 0.0601(15) 0.0465(13) 0.0140(12) 0.0031(11) -0.0028(13) 
C14 0.081(3) 0.081(3) 0.065(3) 0.034(3) 0.016(2) 0.014(3) 
C15 0.099(4) 0.074(3) 0.086(3) 0.028(3) 0.020(3) -0.003(3) 
C16 0.054(2) 0.063(3) 0.066(2) -0.010(2) 0.008(2) 0.012(2) 
O3 0.105(2) 0.0893(18) 0.0496(13) 0.0138(14) 0.0369(14) 0.0278(16) 
F 0.0803(15) 0.1173(19) 0.0988(16) 0.0152(15) 0.0311(13) 0.0332(15) 
C17 0.0417(19) 0.047(2) 0.0528(19) 0.0005(18) 0.0020(16) 0.0000(17) 
C18 0.062(2) 0.059(3) 0.084(3) 0.001(2) -0.016(2) 0.001(2) 
C19 0.073(3) 0.048(3) 0.118(4) 0.006(3) -0.005(3) -0.002(2) 
C20 0.053(2) 0.070(3) 0.088(3) 0.018(3) 0.009(2) 0.009(2) 
C21 0.067(3) 0.087(3) 0.058(2) 0.012(3) -0.004(2) 0.013(3) 
C22 0.072(3) 0.059(3) 0.053(2) -0.004(2) 0.0016(19) 0.010(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 
C1 C12 1.375(4) . ? 
C1 C2 1.409(4) . ? 
C1 C13 1.483(4) . ? 
C2 C3 1.385(4) . ? 
C2 C16 1.435(4) . ? 
C3 N 1.372(4) . ? 
C3 C17 1.483(4) . ? 
N C12 1.399(3) . ? 
N C4 1.404(4) . ? 
C4 C5 1.330(4) . ? 
C4 H4 0.98(3) . ? 
C5 C6 1.428(4) . ? 
C5 H5 1.01(3) . ? 
C6 C7 1.395(4) . ? 
C6 C11 1.410(4) . ? 
C7 C8 1.371(5) . ? 
C7 H7 0.96(3) . ? 
C8 C9 1.381(5) . ? 
C8 H8 0.96(3) . ? 
C9 C10 1.386(5) . ? 
C9 H9 0.88(3) . ? 
C10 C11 1.396(4) . ? 
C10 H10 0.96(3) . ? 
C11 C12 1.448(4) . ? 
C13 O1 1.197(3) . ? 
C13 O2 1.324(4) . ? 
O2 C14 1.461(4) . ? 
C14 C15 1.479(6) . ? 
C14 H14A 1.14(4) . ? 
C14 H14B 0.98(4) . ? 
C15 H15A 0.97(4) . ? 
C15 H15B 1.03(4) . ? 
C15 H15C 1.02(3) . ? 
C16 O3 1.226(4) . ? 
C16 F 1.300(4) . ? 
C17 C22 1.364(4) . ? 
C17 C18 1.374(4) . ? 
C18 C19 1.378(5) . ? 
C18 H18 0.96(3) . ? 
C19 C20 1.359(5) . ? 
C19 H19 0.95(4) . ? 
C20 C21 1.361(5) . ? 
C20 H20 0.99(4) . ? 
C21 C22 1.378(5) . ? 
C21 H21 0.93(4) . ? 
C22 H22 0.93(3) . ? 

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 
C12 C1 C2 107.7(2) . . ? 
C12 C1 C13 127.8(3) . . ? 
C2 C1 C13 124.5(3) . . ? 
C3 C2 C1 108.8(3) . . ? 
C3 C2 C16 127.1(3) . . ? 
C1 C2 C16 124.0(3) . . ? 
N C3 C2 106.4(3) . . ? 
N C3 C17 121.6(3) . . ? 
C2 C3 C17 132.0(3) . . ? 
C3 N C12 110.3(2) . . ? 
C3 N C4 127.7(3) . . ? 
C12 N C4 122.0(3) . . ? 
C5 C4 N 119.5(3) . . ? 
C5 C4 H4 127.2(18) . . ? 
N C4 H4 113.0(18) . . ? 
C4 C5 C6 122.2(3) . . ? 
C4 C5 H5 122.6(15) . . ? 
C6 C5 H5 115.1(15) . . ? 
C7 C6 C11 118.9(3) . . ? 
C7 C6 C5 121.6(3) . . ? 
C11 C6 C5 119.4(3) . . ? 
C8 C7 C6 121.6(3) . . ? 
C8 C7 H7 120.8(17) . . ? 
C6 C7 H7 117.6(17) . . ? 
C7 C8 C9 119.5(4) . . ? 
C7 C8 H8 121.6(18) . . ? 
C9 C8 H8 118.9(18) . . ? 
C8 C9 C10 120.5(4) . . ? 
C8 C9 H9 118(2) . . ? 
C10 C9 H9 121(2) . . ? 
C9 C10 C11 120.4(4) . . ? 
C9 C10 H10 117.1(18) . . ? 
C11 C10 H10 122.3(18) . . ? 
C10 C11 C6 119.0(3) . . ? 
C10 C11 C12 122.5(3) . . ? 
C6 C11 C12 118.5(3) . . ? 
C1 C12 N 106.8(2) . . ? 
C1 C12 C11 134.9(3) . . ? 
N C12 C11 118.3(3) . . ? 
O1 C13 O2 123.6(3) . . ? 
O1 C13 C1 124.8(3) . . ? 
O2 C13 C1 111.5(3) . . ? 
C13 O2 C14 117.1(3) . . ? 
O2 C14 C15 106.7(3) . . ? 
O2 C14 H14A 104.9(18) . . ? 
C15 C14 H14A 113.2(19) . . ? 
O2 C14 H14B 106(2) . . ? 
C15 C14 H14B 115(2) . . ? 
H14A C14 H14B 111(3) . . ? 
C14 C15 H15A 111(2) . . ? 
C14 C15 H15B 118(3) . . ? 
H15A C15 H15B 99(3) . . ? 
C14 C15 H15C 110.8(19) . . ? 
H15A C15 H15C 111(3) . . ? 
H15B C15 H15C 106(3) . . ? 
O3 C16 F 118.5(3) . . ? 
O3 C16 C2 123.5(3) . . ? 
F C16 C2 118.0(3) . . ? 
C22 C17 C18 117.9(3) . . ? 
C22 C17 C3 122.2(3) . . ? 
C18 C17 C3 119.9(3) . . ? 
C17 C18 C19 120.8(4) . . ? 
C17 C18 H18 115(2) . . ? 
C19 C18 H18 124(2) . . ? 
C20 C19 C18 120.8(4) . . ? 
C20 C19 H19 117(2) . . ? 
C18 C19 H19 122(2) . . ? 
C19 C20 C21 118.6(4) . . ? 
C19 C20 H20 120(2) . . ? 
C21 C20 H20 122(2) . . ? 
C20 C21 C22 120.9(4) . . ? 
C20 C21 H21 124(2) . . ? 
C22 C21 H21 115(2) . . ? 
C17 C22 C21 121.0(4) . . ? 
C17 C22 H22 121.8(16) . . ? 
C21 C22 H22 117.2(16) . . ? 

_diffrn_measured_fraction_theta_max    0.475 
_diffrn_reflns_theta_full              27.51 
_diffrn_measured_fraction_theta_full   0.475 
_refine_diff_density_max    0.162 
_refine_diff_density_min   -0.196 
_refine_diff_density_rms    0.041