# Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2002


data_hrdat
_database_code_CSD                  178733

_journal_coden_Cambridge      182

loop_
_publ_author_name
_publ_author_address
'Andree Parlier'
;
Laboratoire de Synthese Organique et Organometallique, UMR 7611
Universite Pierre et Marie Curie,
4, Place Jussieu
75252 Paris cedex 05, France
;
'Bernard Denise'
;
Laboratoire de Synthese Organique et Organometallique, UMR 7611
Universite Pierre et Marie Curie,
4, Place Jussieu
75252 Paris cedex 05, France
;
'Jean-Claude Daran'
;
Laboratoire de Chimie de Coordination
CNRS UPR8241
205 Route de Narbonne
31077 Toulouse cedex, France
;
'Henri Rudler'
;
Laboratoire de Synthese Organique et Organometallique, UMR 7611
Universite Pierre et Marie Curie,
4, Place Jussieu
75252 Paris cedex 05, France
;


_publ_contact_author_name      'Dr H Rudler'
_publ_contact_author_address
;
Laboratoire de Chimie Organique
URa 408
Universite Pierre et Marie Curie
T45, 4 et M. Curie
T45, 4 Place Jussieu
Paris Cedex 05
75252
FRANCE
;
_publ_contact_author_email       daran@lcc-toulouse.fr


_publ_requested_journal       'J. Chem. Soc., Chem. Comm.'
_publ_requested_coeditor_name    ?
_publ_contact_letter            # Include date of submission
;
Please consider this CIF submission for publication
in the Journal of the Chemical Society, Chemical Communication
;

#------------------ TITLE AND AUTHOR LIST------------------------------------#

_publ_section_title
;
One pot synthesis of nitrogen-containing polycyclic X-lactones by
double nucleophilic addition of bis (trimethysilyl) ketene acetals to
pyridines
;

_publ_section_title_footnote
;
?
;


#======================================================================== 
_publ_section_references
;
Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C. , 
Guagliardi, A., Moliterni, A.G.G., Polidori, G.,Spagna, R.(1999). SIR97.  
J. Appl. Cryst. 32, 115-119.

Burnett M. N., Johnson C. K. (1996). ORTEP-III-Report ORNL-6895,
Oak Ridge National Laboratory, Oak Ridge, Tennessee.

Crysalis v.169, Oxford-Diffraction, Oxford, 2001.

CrysalisRed v.169, Oxford-Diffraction, Oxford, 2001.

Farrugia, L. J. (1997). ORTEP-3 for Windows. J. Appl. Cryst. 30, 565.

Farrugia, L. J. (1999). WinGX. J. Appl. Cryst. 32, 837-838.

Sheldrick, G.M. (1997). SHELXL97. Program for crystal structure
refinement. University of Gottingen, Germany.

;

_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_formula_moiety          'C15 H14 I1 N1 O4'
_chemical_formula_structural      'C15 H14 I1 N1 O4'
_chemical_formula_sum             'C15 H14 I1 N1 O4'
_chemical_compound_source         'synthesis as described'
_chemical_formula_weight          399.17

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'
'I'  'I'  -0.4742   1.8119
'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'

_symmetry_cell_setting            monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number       14 

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

_cell_length_a                    6.1448(5)
_cell_length_b                    12.5047(12)
_cell_length_c                    18.9654(14)
_cell_angle_alpha                 90.00
_cell_angle_beta                  92.967(6)
_cell_angle_gamma                 90.00
_cell_volume                      1455.3(2)
_cell_formula_units_Z             4
_cell_measurement_temperature     180(2)
_cell_measurement_reflns_used     10000
_cell_measurement_theta_min       3.43
_cell_measurement_theta_max       25.02

_exptl_crystal_description        prism
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.16
_exptl_crystal_size_mid           0.06
_exptl_crystal_size_min           0.03
_exptl_crystal_density_meas       'not measured'
_exptl_crystal_density_diffrn     1.822
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              784
_exptl_absorpt_coefficient_mu     2.216
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;
_exptl_absorpt_correction_T_min   0.5938
_exptl_absorpt_correction_T_max   0.6860

_diffrn_ambient_temperature       180(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   'Oxford-Diffraction Xcalibur'
_diffrn_measurement_method        '\w,\f scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          0
_diffrn_standards_interval_count  0
_diffrn_standards_interval_time   0
_diffrn_standards_decay_%         none
_diffrn_reflns_number             7143
_diffrn_reflns_av_R_equivalents   0.0889
_diffrn_reflns_av_sigmaI/netI     0.0692
_diffrn_reflns_limit_h_min        -7
_diffrn_reflns_limit_h_max        6
_diffrn_reflns_limit_k_min        -14
_diffrn_reflns_limit_k_max        14
_diffrn_reflns_limit_l_min        -22
_diffrn_reflns_limit_l_max        22
_diffrn_reflns_theta_min          3.43
_diffrn_reflns_theta_max          25.02
_reflns_number_total              2514
_reflns_number_gt                 2116
_reflns_threshold_expression      >2\s(I)

_computing_data_collection        'CRYSALIS 169, Oxford-Diffraction, 2001'
_computing_cell_refinement        'CRYSALISRED 169,Oxford-Diffraction, 2001'
_computing_data_reduction         'CRYSALISRED 169,Oxford-Diffraction, 2001'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'Ortep-3 for Windows(Farrugia,1997)'
_computing_publication_material   'WinGX (Farrugia, 1999)'

_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^)+(0.0901P)^2^+4.4481P] 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      none
_refine_ls_extinction_coef        ?
_refine_ls_number_reflns          2514
_refine_ls_number_parameters      191
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0799
_refine_ls_R_factor_gt            0.0660
_refine_ls_wR_factor_ref          0.1686
_refine_ls_wR_factor_gt           0.1593
_refine_ls_goodness_of_fit_ref    1.123
_refine_ls_restrained_S_all       1.123
_refine_ls_shift/su_max           0.006
_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
C1 C 0.2484(11) 0.0907(6) -0.0811(4) 0.0199(15) Uani 1 1 d . . .
H1 H 0.3061 0.0187 -0.0668 0.024 Uiso 1 1 calc R . .
C2 C 0.1678(11) 0.2685(7) -0.1669(4) 0.0226(16) Uani 1 1 d . . .
H21 H 0.1253 0.3344 -0.1885 0.027 Uiso 1 1 calc R . .
C3 C 0.0428(11) 0.1840(6) -0.1777(4) 0.0190(15) Uani 1 1 d . . .
H31 H -0.0875 0.1910 -0.2065 0.023 Uiso 1 1 calc R . .
C4 C 0.0986(10) 0.0773(6) -0.1462(4) 0.0185(15) Uani 1 1 d . . .
H41 H -0.0379 0.0404 -0.1332 0.022 Uiso 1 1 calc R . .
C5 C 0.2235(10) 0.0052(6) -0.1975(4) 0.0195(15) Uani 1 1 d . . .
H51 H 0.1500 0.0134 -0.2455 0.023 Uiso 1 1 calc R . .
C6 C 0.4618(11) 0.0381(6) -0.2033(4) 0.0220(16) Uani 1 1 d . . .
C11 C 0.4765(12) 0.3583(6) -0.1101(4) 0.0221(17) Uani 1 1 d . . .
C12 C 0.7999(15) 0.4315(7) -0.0595(6) 0.048(3) Uani 1 1 d . . .
H12A H 0.8095 0.4726 -0.1032 0.072 Uiso 1 1 calc R . .
H12B H 0.9465 0.4099 -0.0422 0.072 Uiso 1 1 calc R . .
H12C H 0.7334 0.4757 -0.0238 0.072 Uiso 1 1 calc R . .
C51 C 0.2087(11) -0.1122(6) -0.1775(4) 0.0189(15) Uani 1 1 d . . .
C52 C 0.0130(12) -0.1654(6) -0.1939(4) 0.0233(17) Uani 1 1 d . . .
H52 H -0.1036 -0.1283 -0.2179 0.028 Uiso 1 1 calc R . .
C53 C -0.0135(13) -0.2717(7) -0.1755(5) 0.0290(19) Uani 1 1 d . . .
H53 H -0.1476 -0.3071 -0.1866 0.035 Uiso 1 1 calc R . .
C54 C 0.1574(14) -0.3261(6) -0.1406(5) 0.0292(19) Uani 1 1 d . . .
H54 H 0.1405 -0.3992 -0.1283 0.035 Uiso 1 1 calc R . .
C55 C 0.3539(12) -0.2737(6) -0.1237(4) 0.0252(17) Uani 1 1 d . . .
H55 H 0.4697 -0.3107 -0.0992 0.030 Uiso 1 1 calc R . .
C56 C 0.3793(13) -0.1678(6) -0.1429(4) 0.0250(18) Uani 1 1 d . . .
H56 H 0.5143 -0.1327 -0.1324 0.030 Uiso 1 1 calc R . .
C7 C 0.4380(11) 0.1601(6) -0.0999(4) 0.0218(17) Uani 1 1 d . . .
H71 H 0.5397 0.1683 -0.0573 0.026 Uiso 1 1 calc R . .
I1 I 0.09436(8) 0.15952(4) 0.00734(3) 0.0289(3) Uani 1 1 d . . .
N1 N 0.3666(9) 0.2645(5) -0.1235(3) 0.0199(13) Uani 1 1 d . . .
O1 O 0.5532(7) 0.1084(4) -0.1558(3) 0.0245(12) Uani 1 1 d . . .
O11 O 0.4136(10) 0.4445(5) -0.1271(4) 0.0379(15) Uani 1 1 d . . .
O12 O 0.6684(9) 0.3377(4) -0.0731(4) 0.0348(15) Uani 1 1 d . . .
O61 O 0.5742(8) 0.0026(4) -0.2462(3) 0.0306(13) 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 0.019(3) 0.022(4) 0.019(4) 0.000(3) -0.001(3) 0.000(3)
C2 0.010(3) 0.031(4) 0.026(4) 0.001(3) -0.004(3) 0.009(3)
C3 0.008(3) 0.020(4) 0.028(4) 0.004(3) -0.001(3) -0.001(3)
C4 0.006(3) 0.022(4) 0.028(4) -0.001(3) -0.002(3) -0.002(3)
C5 0.012(3) 0.018(4) 0.029(4) -0.002(3) 0.000(3) -0.001(3)
C6 0.014(3) 0.020(4) 0.031(4) 0.007(3) -0.003(3) 0.003(3)
C11 0.015(3) 0.019(4) 0.032(4) -0.004(3) -0.002(3) 0.000(3)
C12 0.032(5) 0.020(5) 0.090(8) -0.003(5) -0.020(5) -0.013(4)
C51 0.016(3) 0.016(4) 0.024(4) -0.004(3) -0.004(3) 0.004(3)
C52 0.015(3) 0.024(4) 0.030(4) -0.004(3) -0.003(3) 0.002(3)
C53 0.021(4) 0.026(4) 0.041(5) -0.012(4) 0.004(3) -0.005(3)
C54 0.033(4) 0.011(4) 0.043(5) -0.007(3) 0.004(4) -0.001(3)
C55 0.022(4) 0.020(4) 0.033(4) 0.000(3) -0.005(3) 0.009(3)
C56 0.018(4) 0.024(4) 0.033(5) -0.002(3) -0.001(3) 0.004(3)
C7 0.009(3) 0.018(4) 0.038(5) -0.001(3) -0.004(3) -0.001(3)
I1 0.0298(3) 0.0298(4) 0.0273(4) -0.0019(2) 0.0029(2) -0.0008(2)
N1 0.013(3) 0.017(3) 0.030(3) 0.007(3) -0.005(3) 0.001(2)
O1 0.008(2) 0.025(3) 0.041(3) -0.001(2) -0.001(2) -0.001(2)
O11 0.034(3) 0.020(3) 0.058(4) 0.002(3) -0.011(3) -0.003(3)
O12 0.019(3) 0.023(3) 0.060(4) -0.002(3) -0.018(3) -0.007(2)
O61 0.023(3) 0.033(3) 0.036(3) 0.007(3) 0.013(2) 0.006(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 C7 1.510(10) . ?
C1 C4 1.511(10) . ?
C1 I1 2.148(7) . ?
C2 C3 1.317(11) . ?
C2 N1 1.438(9) . ?
C3 C4 1.493(10) . ?
C4 C5 1.558(10) . ?
C5 C51 1.521(10) . ?
C5 C6 1.530(9) . ?
C6 O61 1.181(10) . ?
C6 O1 1.360(9) . ?
C11 O11 1.184(9) . ?
C11 O12 1.365(9) . ?
C11 N1 1.370(9) . ?
C12 O12 1.439(9) . ?
C51 C52 1.395(10) . ?
C51 C56 1.394(11) . ?
C52 C53 1.386(11) . ?
C53 C54 1.390(12) . ?
C54 C55 1.396(11) . ?
C55 C56 1.385(11) . ?
C7 N1 1.441(9) . ?
C7 O1 1.457(10) . ?

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
C7 C1 C4 108.4(6) . . ?
C7 C1 I1 109.3(5) . . ?
C4 C1 I1 114.1(5) . . ?
C3 C2 N1 122.1(7) . . ?
C2 C3 C4 122.4(7) . . ?
C3 C4 C1 110.2(6) . . ?
C3 C4 C5 112.2(6) . . ?
C1 C4 C5 106.0(5) . . ?
C51 C5 C6 110.3(6) . . ?
C51 C5 C4 111.4(6) . . ?
C6 C5 C4 113.2(6) . . ?
O61 C6 O1 117.6(6) . . ?
O61 C6 C5 123.0(7) . . ?
O1 C6 C5 119.4(6) . . ?
O11 C11 O12 125.0(7) . . ?
O11 C11 N1 125.3(7) . . ?
O12 C11 N1 109.8(6) . . ?
C52 C51 C56 119.1(7) . . ?
C52 C51 C5 117.8(6) . . ?
C56 C51 C5 123.1(7) . . ?
C53 C52 C51 120.8(7) . . ?
C52 C53 C54 119.6(7) . . ?
C53 C54 C55 120.2(7) . . ?
C56 C55 C54 119.8(7) . . ?
C55 C56 C51 120.6(7) . . ?
N1 C7 O1 109.1(6) . . ?
N1 C7 C1 111.6(6) . . ?
O1 C7 C1 109.1(6) . . ?
C11 N1 C2 118.2(6) . . ?
C11 N1 C7 125.4(6) . . ?
C2 N1 C7 116.4(6) . . ?
C6 O1 C7 124.7(5) . . ?
C11 O12 C12 113.6(6) . . ?

_diffrn_measured_fraction_theta_max    0.976
_diffrn_reflns_theta_full              25.02
_diffrn_measured_fraction_theta_full   0.976
_refine_diff_density_max    1.716
_refine_diff_density_min   -1.313
_refine_diff_density_rms    0.203

#====END