# Supplementary Material (ESI) for New Journal of Chemistry
# This journal is (c) The Royal Society of Chemistry and 
# The Centre National de la Recherche Scientifique, 2008


data_global

_journal_coden_Cambridge         440

loop_
_publ_author_name
'Michel Fourmigue'
'Pascale Auban-Senzier'
'P Cauliez'
'Rodolphe Clerac'
'Cecile Meziere'

_publ_contact_author_name        'Marc Fourmigue'
_publ_contact_author_address     
;
Sciences Chimiques de Rennes
CNRS
Bat 10C
Campus de Beaulieu
RENNES
35042
FRANCE
;

_publ_contact_author_email       MARC.FOURMIGUE@UNIV-RENNES1.FR

_publ_requested_journal          'New Journal of Chemistry'

_publ_section_title              
;
Square-lattice hybrid organic-inorganic conducting
layers in the ? phase of a TTF tertiary amide derivative.
;

data_import
_database_code_depnum_ccdc_archive 'CCDC 681961'

_audit_creation_date             2007-05-20T13:32:11-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

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

_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         '2(C11 H11 N O S6), C2 H3 Cl3, 2(Au Br2)'
_chemical_formula_sum            'C24 H25 Au2 Br4 Cl3 N2 O2 S12'
_chemical_formula_weight         1578.15
_chemical_compound_source        'synthesis as described'

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
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                   37.1481(5)
_cell_length_b                   11.0741(2)
_cell_length_c                   10.5643(2)
_cell_angle_alpha                90
_cell_angle_beta                 92.0260(10)
_cell_angle_gamma                90
_cell_volume                     4343.24(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    26639
_cell_measurement_theta_min      2.546
_cell_measurement_theta_max      27.485
_cell_measurement_wavelength     0.71073

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

_exptl_crystal_description       prism
_exptl_crystal_colour            black
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.04
_exptl_crystal_density_diffrn    2.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2948
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.012
-1 0 0 0.026
1 -6 -8 0.145
-1 5 6 0.206
3 -1 -1 0.12
-7 -4 3 0.143
3 4 0 0.126
-5 -7 -8 0.142

_exptl_special_details           
;
?
;

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

_exptl_absorpt_coefficient_mu    11.219
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
(see. N.W. Alcock (1970). Cryst. Computing, p271)
;
_exptl_absorpt_correction_T_min  0.0502
_exptl_absorpt_correction_T_max  0.6522

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

_diffrn_source                   'Enraf Nonius FR590'
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 9
_diffrn_orient_matrix_type       'by Nonius Collect from scalepack cell'
_diffrn_orient_matrix_ub_11      -0.99538E-2
_diffrn_orient_matrix_ub_12      0.206432E-1
_diffrn_orient_matrix_ub_13      0.84021E-1
_diffrn_orient_matrix_ub_21      0.34718E-2
_diffrn_orient_matrix_ub_22      -0.855414E-1
_diffrn_orient_matrix_ub_23      0.281967E-1
_diffrn_orient_matrix_ub_31      0.247873E-1
_diffrn_orient_matrix_ub_32      0.202707E-1
_diffrn_orient_matrix_ub_33      0.334238E-1
_diffrn_measurement_device       '95mm CCD camera on \k-goniostat'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_reflns_av_R_equivalents  0.112
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_number            45469
_diffrn_reflns_limit_h_min       -48
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.1
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_reflns_number_total             4979
_reflns_number_gt                4145
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_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^)+(0.0707P)^2^+15.2138P] 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     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_coef       0.00080(8)
_refine_ls_number_reflns         4979
_refine_ls_number_parameters     222
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0423
_refine_ls_wR_factor_ref         0.1305
_refine_ls_wR_factor_gt          0.1213
_refine_ls_goodness_of_fit_ref   1.07
_refine_ls_restrained_S_all      1.07
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.599
_refine_diff_density_min         -1.178
_refine_diff_density_rms         0.15

#----------------------------------------------------------------------------#
# 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'
Au Au -2.0133 8.8022 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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 0.006 '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'

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
Au1 Au 0.5 0 0 0.06044(15) Uani 1 2 d S . .
Br1 Br 0.55187(2) 0.03964(10) 0.13052(8) 0.0818(3) Uani 1 1 d . . .
Au2 Au 0.25 0.75 0 0.07859(19) Uani 1 2 d S . .
Br2 Br 0.18853(3) 0.75113(8) 0.05776(9) 0.0914(3) Uani 1 1 d . . .
S1 S 0.31650(3) 0.62302(12) 0.31104(12) 0.0400(3) Uani 1 1 d . . .
S2 S 0.30369(3) 0.42906(13) 0.13115(13) 0.0445(3) Uani 1 1 d . . .
S3 S 0.23369(3) 0.62803(12) 0.37565(12) 0.0411(3) Uani 1 1 d . . .
S4 S 0.21870(3) 0.42737(11) 0.20685(12) 0.0401(3) Uani 1 1 d . . .
S5 S 0.16003(3) 0.66424(11) 0.45373(12) 0.0397(3) Uani 1 1 d . . .
S6 S 0.14053(3) 0.41958(13) 0.25120(13) 0.0457(3) Uani 1 1 d . . .
O1 O 0.39050(11) 0.6461(4) 0.3954(4) 0.0566(10) Uani 1 1 d . . .
N1 N 0.41381(12) 0.6552(5) 0.1985(5) 0.0520(11) Uani 1 1 d . . .
C1 C 0.35358(13) 0.5713(4) 0.2317(5) 0.0366(9) Uani 1 1 d . . .
C2 C 0.34708(14) 0.4808(5) 0.1484(6) 0.0437(11) Uani 1 1 d . . .
H2 H 0.3655 0.4477 0.102 0.052 Uiso 1 1 calc R . .
C3 C 0.28609(13) 0.5259(4) 0.2387(4) 0.0341(9) Uani 1 1 d . . .
C4 C 0.25012(13) 0.5267(4) 0.2689(4) 0.0330(9) Uani 1 1 d . . .
C5 C 0.18908(12) 0.5813(4) 0.3620(4) 0.0318(9) Uani 1 1 d . . .
C6 C 0.18229(13) 0.4876(4) 0.2838(5) 0.0347(9) Uani 1 1 d . . .
C7 C 0.11644(13) 0.6032(5) 0.4055(5) 0.0456(12) Uani 1 1 d . . .
H7A H 0.0991 0.6241 0.4685 0.055 Uiso 1 1 calc R . .
H7B H 0.1086 0.64 0.326 0.055 Uiso 1 1 calc R . .
C8 C 0.11699(14) 0.4678(5) 0.3896(5) 0.0446(11) Uani 1 1 d . . .
H8A H 0.0924 0.4384 0.3832 0.053 Uiso 1 1 calc R . .
H8B H 0.1285 0.4318 0.4644 0.053 Uiso 1 1 calc R . .
C9 C 0.38791(13) 0.6273(5) 0.2797(5) 0.0424(11) Uani 1 1 d . . .
C10 C 0.40935(19) 0.6449(7) 0.0617(7) 0.0651(17) Uani 1 1 d . . .
H10A H 0.4312 0.6691 0.023 0.098 Uiso 1 1 calc R . .
H10B H 0.39 0.6961 0.0322 0.098 Uiso 1 1 calc R . .
H10C H 0.404 0.5626 0.0395 0.098 Uiso 1 1 calc R . .
C11 C 0.44870(11) 0.7029(4) 0.2521(5) 0.083(2) Uani 1 1 d . . .
H11A H 0.4647 0.7187 0.1846 0.124 Uiso 1 1 calc R . .
H11B H 0.4594 0.6442 0.3088 0.124 Uiso 1 1 calc R . .
H11C H 0.4445 0.7763 0.2976 0.124 Uiso 1 1 calc R . .
Cl1 Cl 0.43934(11) 0.3508(4) 0.2322(5) 0.178(5) Uani 0.5 1 d PR . .
Cl2 Cl 0.49954(11) 0.4124(4) 0.0962(5) 0.185(4) Uani 0.5 1 d PR . .
Cl3 Cl 0.45330(11) 0.3386(4) 0.1351(5) 0.291(12) Uani 0.5 1 d PR . .
C13 C 0.48994(11) 0.2969(4) 0.2164(5) 0.216(9) Uiso 1 1 d 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
Au1 0.0470(2) 0.0722(3) 0.0621(2) -0.00334(16) 0.00211(15) 0.00689(15)
Br1 0.0533(4) 0.1145(7) 0.0772(5) -0.0127(5) -0.0060(3) 0.0057(4)
Au2 0.1209(4) 0.0564(3) 0.0561(2) 0.00608(16) -0.0306(2) -0.0057(2)
Br2 0.1206(8) 0.0820(6) 0.0693(5) 0.0088(4) -0.0277(5) -0.0051(5)
S1 0.0301(5) 0.0467(7) 0.0435(6) -0.0141(5) 0.0045(4) -0.0042(5)
S2 0.0347(6) 0.0476(7) 0.0518(7) -0.0195(6) 0.0087(5) -0.0050(5)
S3 0.0294(5) 0.0466(7) 0.0474(6) -0.0174(5) 0.0043(5) -0.0052(5)
S4 0.0312(5) 0.0421(6) 0.0474(6) -0.0160(5) 0.0056(5) -0.0044(5)
S5 0.0337(6) 0.0397(6) 0.0462(6) -0.0104(5) 0.0091(5) -0.0028(5)
S6 0.0315(6) 0.0536(7) 0.0523(7) -0.0172(6) 0.0052(5) -0.0098(5)
O1 0.045(2) 0.067(3) 0.057(2) -0.006(2) -0.0075(18) -0.0062(19)
N1 0.029(2) 0.051(3) 0.076(3) -0.001(2) 0.007(2) -0.0016(19)
C1 0.032(2) 0.035(2) 0.043(2) 0.0001(19) 0.0049(18) -0.0017(18)
C2 0.032(2) 0.044(3) 0.055(3) -0.007(2) 0.011(2) 0.000(2)
C3 0.033(2) 0.036(2) 0.033(2) -0.0028(17) 0.0022(17) 0.0001(18)
C4 0.032(2) 0.033(2) 0.034(2) -0.0027(17) -0.0001(17) -0.0008(17)
C5 0.029(2) 0.035(2) 0.031(2) 0.0012(17) 0.0045(16) -0.0050(17)
C6 0.031(2) 0.038(2) 0.035(2) -0.0006(18) 0.0036(17) -0.0013(17)
C7 0.030(2) 0.054(3) 0.053(3) -0.008(2) 0.001(2) 0.003(2)
C8 0.035(2) 0.050(3) 0.049(3) -0.007(2) 0.010(2) -0.009(2)
C9 0.030(2) 0.038(2) 0.059(3) -0.001(2) 0.001(2) 0.0021(19)
C10 0.058(4) 0.063(4) 0.076(4) 0.003(3) 0.028(3) -0.007(3)
C11 0.034(3) 0.086(5) 0.128(7) -0.006(5) 0.005(4) -0.018(3)
Cl1 0.171(8) 0.117(6) 0.248(11) 0.064(7) 0.045(8) 0.049(6)
Cl2 0.263(12) 0.157(7) 0.142(6) -0.008(6) 0.099(7) 0.004(8)
Cl3 0.260(14) 0.183(11) 0.41(2) 0.145(13) -0.241(16) -0.120(11)

#----------------------------------------------------------------------------#
# 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
Au1 Br1 2.3706(8) 5_655 ?
Au1 Br1 2.3706(8) . ?
Au2 Br2 2.3843(13) . ?
Au2 Br2 2.3843(13) 7_565 ?
S1 C3 1.719(5) . ?
S1 C1 1.735(5) . ?
S2 C3 1.710(5) . ?
S2 C2 1.714(5) . ?
S3 C4 1.718(5) . ?
S3 C5 1.737(4) . ?
S4 C4 1.717(5) . ?
S4 C6 1.736(5) . ?
S5 C5 1.738(5) . ?
S5 C7 1.811(5) . ?
S6 C6 1.748(5) . ?
S6 C8 1.811(5) . ?
O1 C9 1.240(7) . ?
N1 C9 1.348(7) . ?
N1 C10 1.453(9) . ?
N1 C11 1.493(6) . ?
C1 C2 1.350(7) . ?
C1 C9 1.491(7) . ?
C3 C4 1.385(7) . ?
C5 C6 1.345(7) . ?
C7 C8 1.509(8) . ?
Cl1 Cl3 1.1728 . ?
Cl1 C13 1.9848 . ?
Cl2 C13 1.846 . ?
Cl2 Cl3 1.9588 . ?
Cl3 C13 1.6489 . ?
C13 C13 1.013(9) 2_655 ?

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
Br1 Au1 Br1 180.00(4) 5_655 . ?
Br2 Au2 Br2 180.000(15) . 7_565 ?
C3 S1 C1 95.7(2) . . ?
C3 S2 C2 95.7(2) . . ?
C4 S3 C5 96.4(2) . . ?
C4 S4 C6 96.0(2) . . ?
C5 S5 C7 102.3(2) . . ?
C6 S6 C8 99.5(2) . . ?
C9 N1 C10 123.8(5) . . ?
C9 N1 C11 118.0(5) . . ?
C10 N1 C11 118.2(5) . . ?
C2 C1 C9 131.4(5) . . ?
C2 C1 S1 115.7(4) . . ?
C9 C1 S1 112.5(4) . . ?
C1 C2 S2 117.6(4) . . ?
C4 C3 S2 123.5(4) . . ?
C4 C3 S1 121.2(4) . . ?
S2 C3 S1 115.3(3) . . ?
C3 C4 S4 123.8(4) . . ?
C3 C4 S3 121.6(4) . . ?
S4 C4 S3 114.6(3) . . ?
C6 C5 S3 116.0(4) . . ?
C6 C5 S5 130.1(4) . . ?
S3 C5 S5 113.9(3) . . ?
C5 C6 S4 116.9(4) . . ?
C5 C6 S6 126.8(4) . . ?
S4 C6 S6 116.3(3) . . ?
C8 C7 S5 112.8(4) . . ?
C7 C8 S6 113.0(4) . . ?
O1 C9 N1 123.8(5) . . ?
O1 C9 C1 116.1(5) . . ?
N1 C9 C1 120.0(5) . . ?
Cl3 Cl1 C13 56.1 . . ?
C13 Cl2 Cl3 51.3 . . ?
Cl1 Cl3 C13 87.7 . . ?
Cl1 Cl3 Cl2 123.6 . . ?
C13 Cl3 Cl2 60.8 . . ?
C13 C13 Cl3 160.0(3) 2_655 . ?
C13 C13 Cl2 109.1(4) 2_655 . ?
Cl3 C13 Cl2 67.9 . . ?
C13 C13 Cl1 128.2(5) 2_655 . ?
Cl3 C13 Cl1 36.2 . . ?
Cl2 C13 Cl1 93.2 . . ?