# Supplementary Material (ESI) for Organic and Biomolecular Chemistry
# This journal is (c) the Royal Society of Chemistry 2009

data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'Florence Mongin'
_publ_contact_author_email       FLORENCE.MONGIN@UNIV-RENNES1.FR

_publ_section_title              
;
Direct metallation of thienopyrimidines using a mixed
lithium-cadmium base and antitumor activity of functionalized derivatives
;
_publ_requested_category         FO
loop_
_publ_author_name
'Florence Mongin'
'Ghenia Bentabed-Ababsa'
'A\"icha Derdour'
'Sidaty Cheikh Sid Ely'
'Stephanie Hesse'
;
F.Lassagne
;
'Ekhlass Nassar'
'Enrico Perspicace'
'Katia Snegaroff'

# Attachment 'CIF_file_Mongin.cif'

#
# CCDC ELECTRONIC DATA DEPOSITION FORM (CIF)
#
# This electronic data deposition form can be used:
#
# (a) WHEN SUBMITTING A PAPER TO A JOURNAL FOR PUBLICATION or
# (b) WHEN SUBMITTING A PRIVATE COMMUNICATION TO THE CCDC
#
#-------------------------------------------------------------------------

data_KS050f1
_database_code_depnum_ccdc_archive 'CCDC 729714'

_audit_creation_date             2009-01-13T09:35:54-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
# CHEMICAL INFORMATION #
#----------------------------------------------------------------------------#

_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C12 H6 Cl1 I1 N2 S1'
_chemical_formula_sum            'C12 H6 Cl I N2 S'
_chemical_formula_weight         372.6
_chemical_compound_source        'synthesis as described'

#----------------------------------------------------------------------------#
# UNIT CELL INFORMATION #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P c a b'
_symmetry_space_group_name_Hall  '-P 2bc 2ac'
_symmetry_Int_Tables_number      61
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y+1/2, z+1/2'
'x+1/2, -y, -z+1/2'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, y-1/2, -z-1/2'
'-x-1/2, y, z-1/2'
'x-1/2, -y-1/2, z'

_cell_length_a                   5.8116(2)
_cell_length_b                   16.7820(6)
_cell_length_c                   24.6525(9)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2404.36(15)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7496
_cell_measurement_theta_min      2.94
_cell_measurement_theta_max      27.45
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
# CRYSTAL INFORMATION #
#----------------------------------------------------------------------------#

_exptl_crystal_description       stick
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.06
_exptl_crystal_density_diffrn    2.059
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1424
_exptl_special_details           
;
?
;

#----------------------------------------------------------------------------#
# ABSORPTION CORRECTION #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    3.035
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[Sheldrick, G.M. (2002). SADABS Bruker AXS Inc., Madison, Wisconsin, USA]
;
_exptl_absorpt_correction_T_min  0.583
_exptl_absorpt_correction_T_max  0.834

#----------------------------------------------------------------------------#
# DATA COLLECTION #
#----------------------------------------------------------------------------#

_diffrn_measurement_device_type  'APEXII, Bruker-AXS'
_diffrn_measurement_method       'CCD rotation images, thin slices'
_diffrn_detector                 'CCD plate'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_reflns_av_R_equivalents  0.0587
_diffrn_reflns_av_unetI/netI     0.0296
_diffrn_reflns_number            27353
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.52
_diffrn_reflns_theta_max         27.46
_diffrn_reflns_theta_full        27.46
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             2743
_reflns_number_gt                2477
_reflns_threshold_expression     >2sigma(I)

#----------------------------------------------------------------------------#
# COMPUTER PROGRAMS USED #
#----------------------------------------------------------------------------#

_computing_data_collection       'Bruker SAINT'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR97 (Altomare et al., 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#----------------------------------------------------------------------------#
# REFINEMENT INFORMATION #
#----------------------------------------------------------------------------#

_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^)+(0.0000P)^2^+3.7051P] 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    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2743
_refine_ls_number_parameters     154
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0296
_refine_ls_R_factor_gt           0.0252
_refine_ls_wR_factor_ref         0.0517
_refine_ls_wR_factor_gt          0.0495
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.453
_refine_diff_density_rms         0.093

#----------------------------------------------------------------------------#
# ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS #
#----------------------------------------------------------------------------#

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 0 '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'
S S 0.1246 0.1234 '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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
I1 I -1.24531(3) -0.162506(10) 0.256917(7) 0.01661(6) Uani 1 d . . .
C1 C -0.9894(4) -0.12890(15) 0.20296(11) 0.0161(5) Uani 1 d . . .
C2 C -0.8307(4) -0.07044(15) 0.21145(11) 0.0161(5) Uani 1 d . . .
H2 H -0.8214 -0.0388 0.2433 0.019 Uiso 1 calc R . .
C3 C -0.6793(4) -0.06324(15) 0.16560(11) 0.0146(5) Uani 1 d . . .
C4 C -0.7334(4) -0.11839(14) 0.12435(11) 0.0139(5) Uani 1 d . . .
S5 S -0.96715(11) -0.17749(4) 0.14086(3) 0.01593(14) Uani 1 d . . .
N6 N -0.5048(3) -0.01052(12) 0.16062(9) 0.0144(4) Uani 1 d . . .
C7 C -0.3900(4) -0.01382(14) 0.11393(10) 0.0140(5) Uani 1 d . . .
N8 N -0.4292(4) -0.06505(12) 0.07211(9) 0.0148(4) Uani 1 d . . .
C9 C -0.5987(4) -0.11596(14) 0.07805(11) 0.0141(5) Uani 1 d . . .
Cl10 Cl -0.65615(11) -0.18066(4) 0.02492(3) 0.02006(14) Uani 1 d . . .
C11 C -0.2007(4) 0.04454(14) 0.10503(11) 0.0138(5) Uani 1 d . . .
C12 C -0.1963(4) 0.11723(15) 0.13298(11) 0.0165(5) Uani 1 d . . .
H12 H -0.3104 0.1286 0.1595 0.02 Uiso 1 calc R . .
C13 C -0.0257(5) 0.17243(15) 0.12193(11) 0.0180(6) Uani 1 d . . .
H13 H -0.0246 0.2219 0.1406 0.022 Uiso 1 calc R . .
C14 C 0.1447(5) 0.15607(15) 0.08365(11) 0.0181(6) Uani 1 d . . .
H14 H 0.2603 0.1945 0.0761 0.022 Uiso 1 calc R . .
C15 C 0.1449(5) 0.08368(15) 0.05665(11) 0.0178(5) Uani 1 d . . .
H15 H 0.2627 0.0717 0.0312 0.021 Uiso 1 calc R . .
C16 C -0.0290(4) 0.02863(15) 0.06709(11) 0.0157(5) Uani 1 d . . .
H16 H -0.0305 -0.0206 0.048 0.019 Uiso 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
I1 0.01344(10) 0.01835(10) 0.01805(11) 0.00286(6) 0.00289(7) -0.00078(6)
C1 0.0166(12) 0.0167(12) 0.0148(14) 0.0031(10) 0.0026(10) 0.0033(10)
C2 0.0173(12) 0.0152(12) 0.0157(14) 0.0005(10) 0.0003(11) 0.0014(10)
C3 0.0146(12) 0.0158(12) 0.0135(14) 0.0003(10) -0.0007(10) 0.0019(10)
C4 0.0138(12) 0.0124(11) 0.0155(14) 0.0018(9) -0.0009(10) 0.0004(9)
S5 0.0151(3) 0.0160(3) 0.0166(4) -0.0004(2) 0.0014(3) -0.0025(2)
N6 0.0139(10) 0.0144(10) 0.0147(12) 0.0008(8) -0.0004(8) 0.0010(8)
C7 0.0127(12) 0.0151(12) 0.0142(14) 0.0025(10) -0.0009(10) 0.0026(9)
N8 0.0129(10) 0.0161(10) 0.0155(12) -0.0007(8) 0.0003(9) 0.0020(8)
C9 0.0145(12) 0.0140(12) 0.0138(14) -0.0015(10) -0.0016(10) 0.0031(9)
Cl10 0.0213(3) 0.0213(3) 0.0177(4) -0.0059(3) 0.0014(3) -0.0042(3)
C11 0.0133(12) 0.0142(12) 0.0139(14) 0.0025(9) -0.0024(10) 0.0011(9)
C12 0.0160(12) 0.0173(12) 0.0162(15) 0.0015(10) -0.0006(10) 0.0028(10)
C13 0.0199(13) 0.0167(12) 0.0176(15) 0.0011(10) -0.0057(11) 0.0001(10)
C14 0.0165(13) 0.0178(13) 0.0201(15) 0.0036(10) -0.0033(11) -0.0036(10)
C15 0.0128(12) 0.0254(14) 0.0153(14) 0.0036(11) -0.0002(10) 0.0005(10)
C16 0.0158(12) 0.0158(12) 0.0156(14) -0.0001(10) -0.0031(10) 0.0007(10)

#----------------------------------------------------------------------------#
# MOLECULAR GEOMETRY #
#----------------------------------------------------------------------------#

_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
I1 C1 2.073(3) . ?
C1 C2 1.363(4) . ?
C1 S5 1.739(3) . ?
C2 C3 1.437(4) . ?
C2 H2 0.95 . ?
C3 N6 1.351(3) . ?
C3 C4 1.410(4) . ?
C4 C9 1.384(4) . ?
C4 S5 1.731(3) . ?
N6 C7 1.332(3) . ?
C7 N8 1.362(3) . ?
C7 C11 1.489(3) . ?
N8 C9 1.312(3) . ?
C9 Cl10 1.734(3) . ?
C11 C16 1.394(4) . ?
C11 C12 1.401(4) . ?
C12 C13 1.384(4) . ?
C12 H12 0.95 . ?
C13 C14 1.395(4) . ?
C13 H13 0.95 . ?
C14 C15 1.385(4) . ?
C14 H14 0.95 . ?
C15 C16 1.393(3) . ?
C15 H15 0.95 . ?
C16 H16 0.95 . ?

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
C2 C1 S5 115.0(2) . . ?
C2 C1 I1 125.6(2) . . ?
S5 C1 I1 119.38(14) . . ?
C1 C2 C3 110.7(2) . . ?
C1 C2 H2 124.6 . . ?
C3 C2 H2 124.6 . . ?
N6 C3 C4 122.1(2) . . ?
N6 C3 C2 125.9(2) . . ?
C4 C3 C2 112.0(2) . . ?
C9 C4 C3 116.7(2) . . ?
C9 C4 S5 130.9(2) . . ?
C3 C4 S5 112.42(19) . . ?
C4 S5 C1 89.81(13) . . ?
C7 N6 C3 115.3(2) . . ?
N6 C7 N8 126.6(2) . . ?
N6 C7 C11 118.0(2) . . ?
N8 C7 C11 115.3(2) . . ?
C9 N8 C7 116.9(2) . . ?
N8 C9 C4 122.4(2) . . ?
N8 C9 Cl10 117.9(2) . . ?
C4 C9 Cl10 119.72(19) . . ?
C16 C11 C12 118.9(2) . . ?
C16 C11 C7 120.1(2) . . ?
C12 C11 C7 120.9(2) . . ?
C13 C12 C11 119.9(2) . . ?
C13 C12 H12 120 . . ?
C11 C12 H12 120 . . ?
C12 C13 C14 120.7(2) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 119.9(2) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 119.5(3) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C15 C16 C11 121.1(2) . . ?
C15 C16 H16 119.5 . . ?
C11 C16 H16 119.5 . . ?

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
S5 C1 C2 C3 -0.1(3) . . . . ?
I1 C1 C2 C3 179.90(18) . . . . ?
C1 C2 C3 N6 179.2(2) . . . . ?
C1 C2 C3 C4 -0.4(3) . . . . ?
N6 C3 C4 C9 -0.2(4) . . . . ?
C2 C3 C4 C9 179.4(2) . . . . ?
N6 C3 C4 S5 -178.96(19) . . . . ?
C2 C3 C4 S5 0.6(3) . . . . ?
C9 C4 S5 C1 -179.1(3) . . . . ?
C3 C4 S5 C1 -0.6(2) . . . . ?
C2 C1 S5 C4 0.4(2) . . . . ?
I1 C1 S5 C4 -179.61(15) . . . . ?
C4 C3 N6 C7 0.7(3) . . . . ?
C2 C3 N6 C7 -178.8(2) . . . . ?
C3 N6 C7 N8 -1.1(4) . . . . ?
C3 N6 C7 C11 177.9(2) . . . . ?
N6 C7 N8 C9 0.7(4) . . . . ?
C11 C7 N8 C9 -178.3(2) . . . . ?
C7 N8 C9 C4 0.0(4) . . . . ?
C7 N8 C9 Cl10 178.79(18) . . . . ?
C3 C4 C9 N8 -0.2(4) . . . . ?
S5 C4 C9 N8 178.3(2) . . . . ?
C3 C4 C9 Cl10 -179.02(18) . . . . ?
S5 C4 C9 Cl10 -0.5(3) . . . . ?
N6 C7 C11 C16 158.7(2) . . . . ?
N8 C7 C11 C16 -22.2(3) . . . . ?
N6 C7 C11 C12 -23.7(3) . . . . ?
N8 C7 C11 C12 155.4(2) . . . . ?
C16 C11 C12 C13 1.2(4) . . . . ?
C7 C11 C12 C13 -176.5(2) . . . . ?
C11 C12 C13 C14 -0.9(4) . . . . ?
C12 C13 C14 C15 -0.5(4) . . . . ?
C13 C14 C15 C16 1.6(4) . . . . ?
C14 C15 C16 C11 -1.3(4) . . . . ?
C12 C11 C16 C15 -0.2(4) . . . . ?
C7 C11 C16 C15 177.6(2) . . . . ?