# Supplementary Material (ESI) for New Journal of Chemistry
# This journal is © The Royal Society of Chemistry and 
# The Centre National de la Recherche Scientifique, 2002

data_cd

_database_code_CSD	182824


_journal_coden_Cambridge      440

_publ_requested_journal       'New Journal of Chemistry'

loop_
_publ_author_name
'Parola, Stephane'
'Bouix, J.'
'Desroches, C.'
'Lamartine, R.'
'Letoffe, J.-M.'
'Perrin, M.'
'Vocanson, F.'

_publ_contact_author_name     	'Dr Stephane Parola'  
_publ_contact_author_address 
;
Laboratoire des Multimateriaux et Interfaces
Universite Claude Bernard-Lyon 1
UMR 5615 CNRS
Villeurbanne cedex
F-69622
FRANCE
;

_publ_contact_author_email       'PAROLA@POP.UNIV-LYON1.FR'

_publ_section_title		
;
Nitration of thiacalix[4]arenes using nitrosium nitrate comlexes :
synthesis and characterization of the tetranitro-, tetraamino-, and
tetra(4-pyridylimino)-tetrahydroxythiacalix[4]arene
;

_audit_creation_method            SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
'C28 H24 N4 O14 S6'
_chemical_formula_weight          832.87

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'
'S'  'S'   0.1246   0.1234
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting            Triclinic
_symmetry_space_group_name_H-M    P-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                    8.2988(17)
_cell_length_b                    9.1492(18)
_cell_length_c                    12.431(3)
_cell_angle_alpha                 93.27(3)
_cell_angle_beta                  107.02(3)
_cell_angle_gamma                 113.53(3)
_cell_volume                      811.0(3)
_cell_formula_units_Z             1
_cell_measurement_temperature     173(2)
_cell_measurement_reflns_used     ?
_cell_measurement_theta_min       ?
_cell_measurement_theta_max       ?

_exptl_crystal_description        ?
_exptl_crystal_colour             ?
_exptl_crystal_size_max           0.38
_exptl_crystal_size_mid           0.10
_exptl_crystal_size_min           0.10
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.705
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              428
_exptl_absorpt_coefficient_mu     0.501
_exptl_absorpt_correction_type    none
_exptl_absorpt_correction_T_min   0.8325
_exptl_absorpt_correction_T_max   0.9516
_exptl_absorpt_process_details    ?

_exptl_special_details
;
?
;

_diffrn_ambient_temperature       173(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        '\w scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_standards_number          ?
_diffrn_standards_interval_count  ?
_diffrn_standards_interval_time   ?
_diffrn_standards_decay_%         ?
_diffrn_reflns_number             5948
_diffrn_reflns_av_R_equivalents   0.0680
_diffrn_reflns_av_sigmaI/netI     0.1130
_diffrn_reflns_limit_h_min        -10
_diffrn_reflns_limit_h_max        10
_diffrn_reflns_limit_k_min        -11
_diffrn_reflns_limit_k_max        11
_diffrn_reflns_limit_l_min        -15
_diffrn_reflns_limit_l_max        15
_diffrn_reflns_theta_min          2.48
_diffrn_reflns_theta_max          27.28
_reflns_number_total              3462
_reflns_number_gt                 2198
_reflns_threshold_expression      >2sigma(I)

_computing_data_collection        'Bruker XSCANS'
_computing_cell_refinement        'Bruker XSCANS'
_computing_data_reduction         'Bruker SHELXTL'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics     'Bruker SHELXTL'
_computing_publication_material   'Bruker SHELXTL'

_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^)+(0.0803P)^2^+0.4804P] 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          3462
_refine_ls_number_parameters      237
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.1103
_refine_ls_R_factor_gt            0.0590
_refine_ls_wR_factor_ref          0.1722
_refine_ls_wR_factor_gt           0.1426
_refine_ls_goodness_of_fit_ref    1.016
_refine_ls_restrained_S_all       1.016
_refine_ls_shift/su_max           0.021
_refine_ls_shift/su_mean          0.002

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
S1 S 0.45939(14) 0.18914(13) 0.49679(9) 0.0193(3) Uani 1 1 d . . .
S7 S 0.82156(15) 0.76869(13) 0.36479(9) 0.0190(3) Uani 1 1 d . . .
C2 C 0.5162(6) 0.3041(5) 0.3925(3) 0.0167(9) Uani 1 1 d . . .
C3 C 0.4189(6) 0.2258(5) 0.2786(4) 0.0196(9) Uani 1 1 d . . .
H3 H 0.3369 0.1129 0.2592 0.024 Uiso 1 1 calc R . .
C4 C 0.4436(6) 0.3159(5) 0.1929(4) 0.0200(9) Uani 1 1 d . . .
C5 C 0.5628(6) 0.4802(5) 0.2177(3) 0.0201(10) Uani 1 1 d . . .
H5 H 0.5738 0.5389 0.1576 0.024 Uiso 1 1 calc R . .
C6 C 0.6649(6) 0.5576(5) 0.3299(4) 0.0187(9) Uani 1 1 d . . .
C8 C 1.0154(6) 0.7636(5) 0.3326(4) 0.0182(9) Uani 1 1 d . . .
C9 C 1.0116(6) 0.7491(5) 0.2200(4) 0.0206(10) Uani 1 1 d . . .
H9 H 0.9060 0.7418 0.1592 0.025 Uiso 1 1 calc R . .
C10 C 1.1642(6) 0.7456(5) 0.1975(4) 0.0208(10) Uani 1 1 d . . .
C11 C 1.3187(6) 0.7562(5) 0.2833(4) 0.0195(9) Uani 1 1 d . . .
H11 H 1.4197 0.7504 0.2650 0.023 Uiso 1 1 calc R . .
C12 C 1.3275(6) 0.7754(5) 0.3962(3) 0.0176(9) Uani 1 1 d . . .
C13 C 1.1749(6) 0.7828(5) 0.4222(3) 0.0186(9) Uani 1 1 d . . .
C14 C 0.6408(6) 0.4698(5) 0.4205(3) 0.0178(9) Uani 1 1 d . . .
O13 O 1.1960(4) 0.8079(4) 0.5345(2) 0.0235(7) Uani 1 1 d . . .
H13 H 1.0994 0.8104 0.5414 0.035 Uiso 1 1 calc R . .
O14 O 0.7301(4) 0.5383(3) 0.5316(2) 0.0220(7) Uani 1 1 d . . .
H14 H 0.8002 0.6372 0.5384 0.033 Uiso 1 1 calc R . .
N4 N 0.3435(5) 0.2302(5) 0.0729(3) 0.0258(9) Uani 1 1 d . . .
O41 O 0.3717(5) 0.3080(4) -0.0022(3) 0.0348(9) Uani 1 1 d . . .
O42 O 0.2382(6) 0.0849(4) 0.0531(3) 0.0447(10) Uani 1 1 d . . .
N10 N 1.1552(6) 0.7231(5) 0.0784(3) 0.0278(9) Uani 1 1 d . . .
O101 O 1.2985(5) 0.7397(5) 0.0610(3) 0.0403(9) Uani 1 1 d . . .
O102 O 1.0041(5) 0.6878(5) 0.0018(3) 0.0429(10) Uani 1 1 d . . .
S50 S 1.05163(16) 0.83080(14) -0.23174(9) 0.0229(3) Uani 1 1 d . . .
O50 O 0.9780(4) 0.8458(3) -0.3570(2) 0.0213(7) Uani 1 1 d . . .
C52 C 1.0703(8) 0.6437(6) -0.2393(4) 0.0333(12) Uani 1 1 d . . .
H52A H 0.9451 0.5532 -0.2737 0.050 Uiso 1 1 calc R . .
H52B H 1.1299 0.6317 -0.1618 0.050 Uiso 1 1 calc R . .
H52C H 1.1463 0.6430 -0.2864 0.050 Uiso 1 1 calc R . .
C51 C 1.2969(7) 0.9611(6) -0.1804(4) 0.0312(12) Uani 1 1 d . . .
H51A H 1.3524 0.9400 -0.2356 0.047 Uiso 1 1 calc R . .
H51B H 1.3561 0.9400 -0.1062 0.047 Uiso 1 1 calc R . .
H51C H 1.3170 1.0748 -0.1713 0.047 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
S1 0.0153(6) 0.0213(6) 0.0174(6) 0.0069(4) 0.0055(4) 0.0039(5)
S7 0.0174(6) 0.0186(6) 0.0198(6) 0.0060(4) 0.0074(5) 0.0056(4)
C2 0.014(2) 0.017(2) 0.017(2) 0.0034(17) 0.0036(18) 0.0062(18)
C3 0.020(2) 0.021(2) 0.018(2) 0.0033(18) 0.0088(19) 0.0073(19)
C4 0.016(2) 0.026(2) 0.015(2) 0.0032(18) 0.0016(18) 0.0081(19)
C5 0.017(2) 0.026(2) 0.014(2) 0.0085(18) 0.0057(19) 0.0062(19)
C6 0.015(2) 0.023(2) 0.017(2) 0.0070(18) 0.0062(18) 0.0059(18)
C8 0.020(2) 0.015(2) 0.017(2) 0.0067(17) 0.0076(18) 0.0035(18)
C9 0.015(2) 0.020(2) 0.018(2) 0.0054(18) 0.0025(18) 0.0006(18)
C10 0.024(2) 0.020(2) 0.016(2) 0.0054(17) 0.0070(19) 0.0068(19)
C11 0.018(2) 0.018(2) 0.018(2) 0.0052(17) 0.0088(19) 0.0018(18)
C12 0.018(2) 0.015(2) 0.015(2) 0.0049(17) 0.0057(18) 0.0036(18)
C13 0.020(2) 0.015(2) 0.018(2) 0.0048(17) 0.0069(19) 0.0035(18)
C14 0.016(2) 0.018(2) 0.014(2) 0.0027(17) 0.0028(18) 0.0048(18)
O13 0.0209(16) 0.0333(18) 0.0155(16) 0.0067(13) 0.0064(13) 0.0108(14)
O14 0.0234(16) 0.0167(15) 0.0161(16) 0.0034(12) 0.0044(13) 0.0011(13)
N4 0.025(2) 0.031(2) 0.018(2) 0.0030(17) 0.0049(17) 0.0107(19)
O41 0.036(2) 0.040(2) 0.0167(17) 0.0072(15) 0.0054(15) 0.0078(17)
O42 0.053(2) 0.029(2) 0.026(2) -0.0011(15) 0.0060(18) -0.0009(19)
N10 0.027(2) 0.036(2) 0.021(2) 0.0079(17) 0.0120(19) 0.0119(19)
O101 0.029(2) 0.069(3) 0.0219(19) 0.0055(17) 0.0134(16) 0.0172(19)
O102 0.034(2) 0.078(3) 0.0167(18) 0.0091(18) 0.0059(17) 0.027(2)
S50 0.0238(6) 0.0269(6) 0.0156(6) 0.0041(5) 0.0075(5) 0.0081(5)
O50 0.0207(16) 0.0247(17) 0.0137(15) 0.0018(12) 0.0029(13) 0.0077(14)
C52 0.041(3) 0.021(3) 0.029(3) 0.006(2) 0.008(2) 0.007(2)
C51 0.029(3) 0.028(3) 0.024(3) 0.003(2) 0.003(2) 0.005(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
S1 C12 1.766(4) 2_766 ?
S1 C2 1.769(4) . ?
S7 C6 1.783(4) . ?
S7 C8 1.785(5) . ?
C2 C3 1.387(6) . ?
C2 C14 1.402(6) . ?
C3 C4 1.396(6) . ?
C4 C5 1.384(6) . ?
C4 N4 1.467(6) . ?
C5 C6 1.371(6) . ?
C6 C14 1.436(5) . ?
C8 C9 1.388(6) . ?
C8 C13 1.398(6) . ?
C9 C10 1.386(6) . ?
C10 C11 1.370(6) . ?
C10 N10 1.459(6) . ?
C11 C12 1.381(6) . ?
C12 C13 1.421(6) . ?
C12 S1 1.766(4) 2_766 ?
C13 O13 1.349(5) . ?
C14 O14 1.334(5) . ?
N4 O41 1.227(5) . ?
N4 O42 1.225(5) . ?
N10 O101 1.222(5) . ?
N10 O102 1.235(5) . ?
S50 O50 1.533(3) . ?
S50 C52 1.779(5) . ?
S50 C51 1.785(5) . ?

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 S1 C2 107.18(19) 2_766 . ?
C6 S7 C8 101.0(2) . . ?
C3 C2 C14 120.4(4) . . ?
C3 C2 S1 116.6(3) . . ?
C14 C2 S1 122.9(3) . . ?
C2 C3 C4 118.8(4) . . ?
C5 C4 C3 122.3(4) . . ?
C5 C4 N4 119.6(4) . . ?
C3 C4 N4 118.1(4) . . ?
C6 C5 C4 119.4(4) . . ?
C5 C6 C14 119.9(4) . . ?
C5 C6 S7 120.6(3) . . ?
C14 C6 S7 119.5(3) . . ?
C9 C8 C13 120.2(4) . . ?
C9 C8 S7 120.3(3) . . ?
C13 C8 S7 119.4(3) . . ?
C10 C9 C8 119.0(4) . . ?
C11 C10 C9 121.9(4) . . ?
C11 C10 N10 119.5(4) . . ?
C9 C10 N10 118.5(4) . . ?
C10 C11 C12 120.0(4) . . ?
C11 C12 C13 119.4(4) . . ?
C11 C12 S1 117.5(3) . 2_766 ?
C13 C12 S1 122.7(3) . 2_766 ?
O13 C13 C8 124.5(4) . . ?
O13 C13 C12 116.3(4) . . ?
C8 C13 C12 119.3(4) . . ?
O14 C14 C2 117.6(3) . . ?
O14 C14 C6 123.3(4) . . ?
C2 C14 C6 119.1(4) . . ?
O41 N4 O42 123.6(4) . . ?
O41 N4 C4 118.0(4) . . ?
O42 N4 C4 118.4(4) . . ?
O101 N10 O102 124.2(4) . . ?
O101 N10 C10 117.5(4) . . ?
O102 N10 C10 118.3(4) . . ?
O50 S50 C52 105.0(2) . . ?
O50 S50 C51 105.9(2) . . ?
C52 S50 C51 96.7(2) . . ?

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
C12 S1 C2 C3 135.1(3) 2_766 . . . ?
C12 S1 C2 C14 -50.1(4) 2_766 . . . ?
C14 C2 C3 C4 -1.7(6) . . . . ?
S1 C2 C3 C4 173.2(3) . . . . ?
C2 C3 C4 C5 0.5(7) . . . . ?
C2 C3 C4 N4 178.4(4) . . . . ?
C3 C4 C5 C6 1.9(7) . . . . ?
N4 C4 C5 C6 -176.0(4) . . . . ?
C4 C5 C6 C14 -2.9(7) . . . . ?
C4 C5 C6 S7 179.3(3) . . . . ?
C8 S7 C6 C5 -77.7(4) . . . . ?
C8 S7 C6 C14 104.6(4) . . . . ?
C6 S7 C8 C9 80.3(4) . . . . ?
C6 S7 C8 C13 -103.1(3) . . . . ?
C13 C8 C9 C10 3.3(6) . . . . ?
S7 C8 C9 C10 180.0(3) . . . . ?
C8 C9 C10 C11 -0.1(6) . . . . ?
C8 C9 C10 N10 177.3(4) . . . . ?
C9 C10 C11 C12 -1.7(6) . . . . ?
N10 C10 C11 C12 -179.2(4) . . . . ?
C10 C11 C12 C13 0.4(6) . . . . ?
C10 C11 C12 S1 -173.1(3) . . . 2_766 ?
C9 C8 C13 O13 175.7(4) . . . . ?
S7 C8 C13 O13 -1.0(6) . . . . ?
C9 C8 C13 C12 -4.6(6) . . . . ?
S7 C8 C13 C12 178.7(3) . . . . ?
C11 C12 C13 O13 -177.5(4) . . . . ?
S1 C12 C13 O13 -4.4(5) 2_766 . . . ?
C11 C12 C13 C8 2.7(6) . . . . ?
S1 C12 C13 C8 175.9(3) 2_766 . . . ?
C3 C2 C14 O14 179.9(4) . . . . ?
S1 C2 C14 O14 5.3(6) . . . . ?
C3 C2 C14 C6 0.7(6) . . . . ?
S1 C2 C14 C6 -173.9(3) . . . . ?
C5 C6 C14 O14 -177.5(4) . . . . ?
S7 C6 C14 O14 0.2(6) . . . . ?
C5 C6 C14 C2 1.7(7) . . . . ?
S7 C6 C14 C2 179.4(3) . . . . ?
C5 C4 N4 O41 1.0(6) . . . . ?
C3 C4 N4 O41 -176.9(4) . . . . ?
C5 C4 N4 O42 -179.7(4) . . . . ?
C3 C4 N4 O42 2.3(6) . . . . ?
C11 C10 N10 O101 -11.1(6) . . . . ?
C9 C10 N10 O101 171.4(4) . . . . ?
C11 C10 N10 O102 168.5(4) . . . . ?
C9 C10 N10 O102 -9.0(6) . . . . ?

_diffrn_measured_fraction_theta_max    0.950
_diffrn_reflns_theta_full              27.28
_diffrn_measured_fraction_theta_full   0.950
_refine_diff_density_max    0.439
_refine_diff_density_min   -0.495
_refine_diff_density_rms    0.109