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


data_sn2
_database_code_CSD                  181455

_journal_coden_Cambridge      207


loop_
_publ_author_name
'Dixneuf, Pierre H.'
'Ben Hadda, Tabi'
'Bitit, Najib'
'Bozec, Hubert le'
'Daoudi, Maria'
'Elkadiri, S.'
'Sam, Najat'
'Toupet, L.'

_publ_contact_author_name     	'Pierre H Dixneuf'  
_publ_contact_author_address 
;
Institut de Chimie de Rennes
CNRS-Universite de Rennes I
Organometalliques et Catalyse
Chimie et Electrochimie Moleculaire
Campus de Beaulieu
Rennes
Cedex
35042
FRANCE
;

_publ_contact_author_email       'DIXNEUF@UNIV-RENNES1.FR'

_publ_requested_journal       'Perkin Transactions 1'

_publ_section_title		
;
Novel trichloro indolizine derivatives via intramolecular acylation
of a bis(chloroacyl)bipyridine
;


_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
'C14 H11 Cl3 N2 O3'
_chemical_formula_weight          361.60

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'
'Cl'  'Cl'   0.1484   0.1585
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting            Monoclinic
_symmetry_space_group_name_H-M    P21/a

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

_cell_length_a                    13.536(2)
_cell_length_b                    7.7870(10)
_cell_length_c                    14.769(2)
_cell_angle_alpha                 90.00
_cell_angle_beta                  97.620(10)
_cell_angle_gamma                 90.00
_cell_volume                      1543.0(4)
_cell_formula_units_Z             4
_cell_measurement_temperature     293(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?

_exptl_crystal_description        block
_exptl_crystal_colour             colourless
_exptl_crystal_size_max           0.35
_exptl_crystal_size_mid           0.25
_exptl_crystal_size_min           0.20
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.557
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              736
_exptl_absorpt_coefficient_mu     0.606
_exptl_absorpt_correction_type    no
_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      0.71069
_diffrn_radiation_type            MoK\a
_diffrn_radiation_source          'fine-focus sealed tube'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Nonius CAD4'
_diffrn_measurement_method        'scan omega'
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         0.4
_diffrn_reflns_number             3492
_diffrn_reflns_av_R_equivalents   0.0207
_diffrn_reflns_av_sigmaI/netI     0.0379
_diffrn_reflns_limit_h_min        0
_diffrn_reflns_limit_h_max        17
_diffrn_reflns_limit_k_min        0
_diffrn_reflns_limit_k_max        9
_diffrn_reflns_limit_l_min        -18
_diffrn_reflns_limit_l_max        18
_diffrn_reflns_theta_min          2.78
_diffrn_reflns_theta_max          26.97
_reflns_number_total              3344
_reflns_number_gt                 2347
_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
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0657P)^2^+2.4469P] 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        0.0016(13)
_refine_ls_extinction_expression
'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^'
_refine_ls_number_reflns          3344
_refine_ls_number_parameters      200
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0937
_refine_ls_R_factor_gt            0.0569
_refine_ls_wR_factor_ref          0.1699
_refine_ls_wR_factor_gt           0.1525
_refine_ls_goodness_of_fit_ref    1.094
_refine_ls_restrained_S_all       1.094
_refine_ls_shift/su_max           0.005
_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
Cl1 Cl 0.90201(10) 0.39686(16) 0.55964(8) 0.0624(4) Uani 1 1 d . . .
Cl2 Cl 0.75380(11) -0.00376(16) 0.69063(9) 0.0678(4) Uani 1 1 d . . .
Cl3 Cl 1.02133(8) 0.28072(16) 0.76819(8) 0.0585(4) Uani 1 1 d . . .
O1 O 0.6328(2) 0.4494(4) 0.51337(17) 0.0503(7) Uani 1 1 d . . .
O2 O 0.8634(3) 0.3270(4) 0.95251(19) 0.0574(8) Uani 1 1 d . . .
O3 O 0.86733(19) 0.5941(3) 0.89517(16) 0.0393(6) Uani 1 1 d . . .
N1 N 0.6617(2) 0.6318(4) 0.82305(19) 0.0360(7) Uani 1 1 d . . .
N2 N 0.7391(2) 0.3829(4) 0.64276(19) 0.0371(7) Uani 1 1 d . . .
C1 C 0.6793(3) 0.5609(5) 0.7452(2) 0.0313(7) Uani 1 1 d . . .
C2 C 0.5810(3) 0.7334(5) 0.8157(3) 0.0447(9) Uani 1 1 d . . .
H2 H 0.5659 0.7876 0.8682 0.054 Uiso 1 1 calc R . .
C3 C 0.5186(3) 0.7631(5) 0.7346(3) 0.0471(10) Uani 1 1 d . . .
H3 H 0.4638 0.8352 0.7341 0.057 Uiso 1 1 calc R . .
C4 C 0.5378(3) 0.6859(5) 0.6552(3) 0.0399(9) Uani 1 1 d . . .
H4 H 0.4973 0.7033 0.6000 0.048 Uiso 1 1 calc R . .
C5 C 0.6202(3) 0.5814(5) 0.6617(2) 0.0325(8) Uani 1 1 d . . .
C6 C 0.6591(3) 0.4699(5) 0.5942(2) 0.0365(8) Uani 1 1 d . . .
C7 C 0.7592(3) 0.4358(5) 0.7344(2) 0.0312(7) Uani 1 1 d . . .
C8 C 0.8050(3) 0.2735(5) 0.6027(3) 0.0407(9) Uani 1 1 d . . .
H8 H 0.7669 0.2122 0.5516 0.049 Uiso 1 1 calc R . .
C9 C 0.8504(3) 0.1430(5) 0.6721(3) 0.0424(9) Uani 1 1 d . . .
H9 H 0.9036 0.0806 0.6471 0.051 Uiso 1 1 calc R . .
C10 C 0.8919(3) 0.2194(5) 0.7651(3) 0.0392(9) Uani 1 1 d . . .
H10 H 0.8891 0.1291 0.8109 0.047 Uiso 1 1 calc R . .
C11 C 0.8326(3) 0.3679(5) 0.7924(2) 0.0331(8) Uani 1 1 d . . .
C12 C 0.8548(3) 0.4255(5) 0.8891(2) 0.0345(8) Uani 1 1 d . . .
C13 C 0.8693(4) 0.6687(6) 0.9854(3) 0.0509(11) Uani 1 1 d . . .
H13A H 0.9265 0.6267 1.0259 0.061 Uiso 1 1 calc R . .
H13B H 0.8093 0.6387 1.0111 0.061 Uiso 1 1 calc R . .
C14 C 0.8760(4) 0.8585(6) 0.9743(4) 0.0701(15) Uani 1 1 d . . .
H14A H 0.8775 0.9130 1.0328 0.084 Uiso 1 1 calc R . .
H14B H 0.8190 0.8984 0.9341 0.084 Uiso 1 1 calc R . .
H14C H 0.9357 0.8864 0.9489 0.084 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
Cl1 0.0686(8) 0.0652(8) 0.0585(7) 0.0011(6) 0.0271(6) -0.0060(6)
Cl2 0.0793(9) 0.0486(7) 0.0757(8) -0.0021(6) 0.0111(7) -0.0211(6)
Cl3 0.0394(6) 0.0647(7) 0.0699(7) -0.0190(6) 0.0016(5) 0.0116(5)
O1 0.0598(18) 0.0605(19) 0.0277(13) -0.0020(13) -0.0052(12) 0.0025(15)
O2 0.083(2) 0.0532(18) 0.0344(15) 0.0060(14) 0.0023(14) 0.0046(17)
O3 0.0442(15) 0.0425(15) 0.0301(13) -0.0072(11) 0.0014(11) -0.0035(12)
N1 0.0368(16) 0.0417(18) 0.0302(15) -0.0021(13) 0.0062(12) 0.0041(14)
N2 0.0444(18) 0.0398(18) 0.0267(14) -0.0057(13) 0.0035(12) 0.0044(14)
C1 0.0314(18) 0.0316(18) 0.0311(17) 0.0018(14) 0.0049(13) -0.0047(15)
C2 0.047(2) 0.046(2) 0.042(2) -0.0094(18) 0.0105(17) 0.0040(19)
C3 0.040(2) 0.042(2) 0.059(3) -0.0016(19) 0.0055(18) 0.0084(18)
C4 0.036(2) 0.040(2) 0.041(2) 0.0057(17) -0.0030(16) 0.0014(16)
C5 0.0327(18) 0.0315(18) 0.0329(17) 0.0028(15) 0.0027(14) -0.0061(15)
C6 0.042(2) 0.0350(19) 0.0320(18) 0.0019(15) 0.0021(15) -0.0040(16)
C7 0.0370(18) 0.0315(18) 0.0256(16) -0.0028(14) 0.0059(13) -0.0021(15)
C8 0.049(2) 0.040(2) 0.0345(18) -0.0078(16) 0.0085(16) 0.0014(18)
C9 0.048(2) 0.035(2) 0.044(2) -0.0061(17) 0.0071(17) 0.0035(18)
C10 0.043(2) 0.036(2) 0.0373(19) -0.0015(16) 0.0005(16) 0.0028(17)
C11 0.0381(19) 0.0327(18) 0.0290(17) -0.0005(14) 0.0062(14) 0.0013(15)
C12 0.0300(18) 0.040(2) 0.0330(18) 0.0003(16) 0.0008(14) 0.0029(16)
C13 0.058(3) 0.058(3) 0.036(2) -0.017(2) 0.0031(18) -0.002(2)
C14 0.084(4) 0.059(3) 0.070(3) -0.026(3) 0.019(3) -0.013(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
Cl1 C8 1.810(4) . ?
Cl2 C9 1.785(4) . ?
Cl3 C10 1.811(4) . ?
O1 C6 1.211(4) . ?
O2 C12 1.204(4) . ?
O3 C12 1.325(5) . ?
O3 C13 1.451(4) . ?
N1 C1 1.325(4) . ?
N1 C2 1.342(5) . ?
N2 C6 1.392(5) . ?
N2 C7 1.406(4) . ?
N2 C8 1.418(5) . ?
C1 C5 1.387(5) . ?
C1 C7 1.480(5) . ?
C2 C3 1.391(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.374(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.471(5) . ?
C7 C11 1.332(5) . ?
C8 C9 1.515(5) . ?
C8 H8 0.9800 . ?
C9 C10 1.533(5) . ?
C9 H9 0.9800 . ?
C10 C11 1.494(5) . ?
C10 H10 0.9800 . ?
C11 C12 1.489(5) . ?
C13 C14 1.491(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C12 O3 C13 116.5(3) . . ?
C1 N1 C2 114.4(3) . . ?
C6 N2 C7 113.0(3) . . ?
C6 N2 C8 124.5(3) . . ?
C7 N2 C8 121.7(3) . . ?
N1 C1 C5 125.1(3) . . ?
N1 C1 C7 125.9(3) . . ?
C5 C1 C7 108.8(3) . . ?
N1 C2 C3 124.3(4) . . ?
N1 C2 H2 117.9 . . ?
C3 C2 H2 117.9 . . ?
C4 C3 C2 120.0(4) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 116.3(3) . . ?
C5 C4 H4 121.8 . . ?
C3 C4 H4 121.8 . . ?
C4 C5 C1 119.8(3) . . ?
C4 C5 C6 131.5(3) . . ?
C1 C5 C6 108.6(3) . . ?
O1 C6 N2 123.4(4) . . ?
O1 C6 C5 131.4(4) . . ?
N2 C6 C5 105.2(3) . . ?
C11 C7 N2 122.4(3) . . ?
C11 C7 C1 133.2(3) . . ?
N2 C7 C1 104.3(3) . . ?
N2 C8 C9 110.0(3) . . ?
N2 C8 Cl1 110.7(3) . . ?
C9 C8 Cl1 110.2(3) . . ?
N2 C8 H8 108.6 . . ?
C9 C8 H8 108.6 . . ?
Cl1 C8 H8 108.6 . . ?
C8 C9 C10 114.4(3) . . ?
C8 C9 Cl2 107.0(3) . . ?
C10 C9 Cl2 107.5(3) . . ?
C8 C9 H9 109.3 . . ?
C10 C9 H9 109.3 . . ?
Cl2 C9 H9 109.3 . . ?
C11 C10 C9 113.3(3) . . ?
C11 C10 Cl3 110.0(3) . . ?
C9 C10 Cl3 111.3(3) . . ?
C11 C10 H10 107.3 . . ?
C9 C10 H10 107.3 . . ?
Cl3 C10 H10 107.3 . . ?
C7 C11 C12 122.5(3) . . ?
C7 C11 C10 121.0(3) . . ?
C12 C11 C10 116.4(3) . . ?
O2 C12 O3 125.5(3) . . ?
O2 C12 C11 122.7(4) . . ?
O3 C12 C11 111.8(3) . . ?
O3 C13 C14 106.9(4) . . ?
O3 C13 H13A 110.4 . . ?
C14 C13 H13A 110.4 . . ?
O3 C13 H13B 110.4 . . ?
C14 C13 H13B 110.4 . . ?
H13A C13 H13B 108.6 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 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
C2 N1 C1 C5 -1.8(5) . . . . ?
C2 N1 C1 C7 -176.1(3) . . . . ?
C1 N1 C2 C3 0.8(6) . . . . ?
N1 C2 C3 C4 0.0(7) . . . . ?
C2 C3 C4 C5 0.0(6) . . . . ?
C3 C4 C5 C1 -0.9(6) . . . . ?
C3 C4 C5 C6 174.9(4) . . . . ?
N1 C1 C5 C4 1.9(6) . . . . ?
C7 C1 C5 C4 177.0(3) . . . . ?
N1 C1 C5 C6 -174.7(3) . . . . ?
C7 C1 C5 C6 0.4(4) . . . . ?
C7 N2 C6 O1 176.3(4) . . . . ?
C8 N2 C6 O1 6.3(6) . . . . ?
C7 N2 C6 C5 -3.6(4) . . . . ?
C8 N2 C6 C5 -173.6(3) . . . . ?
C4 C5 C6 O1 5.8(7) . . . . ?
C1 C5 C6 O1 -178.1(4) . . . . ?
C4 C5 C6 N2 -174.3(4) . . . . ?
C1 C5 C6 N2 1.9(4) . . . . ?
C6 N2 C7 C11 179.8(3) . . . . ?
C8 N2 C7 C11 -9.9(6) . . . . ?
C6 N2 C7 C1 3.8(4) . . . . ?
C8 N2 C7 C1 174.1(3) . . . . ?
N1 C1 C7 C11 -2.8(7) . . . . ?
C5 C1 C7 C11 -177.8(4) . . . . ?
N1 C1 C7 N2 172.6(3) . . . . ?
C5 C1 C7 N2 -2.5(4) . . . . ?
C6 N2 C8 C9 -154.5(3) . . . . ?
C7 N2 C8 C9 36.3(5) . . . . ?
C6 N2 C8 Cl1 83.4(4) . . . . ?
C7 N2 C8 Cl1 -85.7(4) . . . . ?
N2 C8 C9 C10 -48.0(5) . . . . ?
Cl1 C8 C9 C10 74.3(4) . . . . ?
N2 C8 C9 Cl2 71.0(3) . . . . ?
Cl1 C8 C9 Cl2 -166.72(19) . . . . ?
C8 C9 C10 C11 35.0(5) . . . . ?
Cl2 C9 C10 C11 -83.7(4) . . . . ?
C8 C9 C10 Cl3 -89.6(4) . . . . ?
Cl2 C9 C10 Cl3 151.7(2) . . . . ?
N2 C7 C11 C12 179.1(3) . . . . ?
C1 C7 C11 C12 -6.2(6) . . . . ?
N2 C7 C11 C10 -5.8(6) . . . . ?
C1 C7 C11 C10 168.9(4) . . . . ?
C9 C10 C11 C7 -7.8(5) . . . . ?
Cl3 C10 C11 C7 117.5(3) . . . . ?
C9 C10 C11 C12 167.6(3) . . . . ?
Cl3 C10 C11 C12 -67.1(4) . . . . ?
C13 O3 C12 O2 -14.5(6) . . . . ?
C13 O3 C12 C11 167.9(3) . . . . ?
C7 C11 C12 O2 129.2(4) . . . . ?
C10 C11 C12 O2 -46.1(5) . . . . ?
C7 C11 C12 O3 -53.1(5) . . . . ?
C10 C11 C12 O3 131.6(3) . . . . ?
C12 O3 C13 C14 -175.7(4) . . . . ?

_diffrn_measured_fraction_theta_max    0.999
_diffrn_reflns_theta_full              26.97
_diffrn_measured_fraction_theta_full   0.999
_refine_diff_density_max    0.366
_refine_diff_density_min   -0.321
_refine_diff_density_rms    0.067