# Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is (c) The Royal Society of Chemistry 2010




data_publication_text
_publ_requested_journal          OBC
_publ_contact_author_name        'Fabienne Grellepois'
_publ_contact_author_address     
;Universit\'e de Reims-Champagne-Ardennes,
Institut de Chimie Mol\'eculaire de Reims,
UMR CNRS 6229,
UFR des Sciences Exactes et Naturelles,
BP 1039, 51687 Reims cedex 2, France
;
_publ_contact_author_email       fabienne.grellepois@univ-reims.fr
_publ_contact_author_phone       '33 3 26 91 31 64'
loop_
_publ_author_name
_publ_author_address
'Fabienne Grellepois'
;Universit\'e de Reims-Champagne-Ardennes,
Institut de Chimie Mol\'eculaire de Reims,
UMR CNRS 6229,
UFR des Sciences Exactes et Naturelles,
BP 1039, 51687 Reims cedex 2, France
;
'Nonnenmacher, Jean'
;Universit\'e de Reims-Champagne-Ardennes,
Institut de Chimie Mol\'eculaire de Reims,
UMR CNRS 6229,
UFR des Sciences Exactes et Naturelles,
BP 1039, 51687 Reims cedex 2, France
;
'Lachaud, Fabien'
;Universit\'e de Reims-Champagne-Ardennes,
Institut de Chimie Mol\'eculaire de Reims,
UMR CNRS 6229,
UFR des Sciences Exactes et Naturelles,
BP 1039, 51687 Reims cedex 2, France
;

'Portella, Charles'
;Universit\'e de Reims-Champagne-Ardenne, 
Institut de Chimie Mol\'eculaire de Reims, UMR CNRS 6229,
UFR des Sciences Exactes et Naturelles,
BP 1039, 51687 Reims cedex 2, France
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H25 F3 N2 O2 S'
_chemical_melting_point          ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?

_diffrn_ambient_temperature      100(2)
_chemical_formula_weight         462.52

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'
F F 0.0171 0.0103 '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           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_int_tables_number      19
_chemical_absolute_configuration ad

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

_cell_length_a                   9.6263(13)
_cell_length_b                   14.1765(14)
_cell_length_c                   16.473(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2248.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4405
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      30.38
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             968
_exptl_absorpt_coefficient_mu    0.193
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;        
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'KAPPA APEXII ICMMO'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18019
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_sigmaI/netI    0.0583
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         30.50
_reflns_number_total             6529
_reflns_number_gt                5364
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_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^)+(0.0559P)^2^+0.0000P] 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_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.06(6)
_refine_ls_number_reflns         6529
_refine_ls_number_parameters     291
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.1031
_refine_ls_wR_factor_gt          0.0978
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

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 0.5544(2) 0.58148(12) 0.78958(10) 0.0168(4) Uani 1 1 d . . .
C2 C 0.5585(2) 0.56971(12) 0.69582(10) 0.0136(3) Uani 1 1 d . . .
C3 C 0.5296(2) 0.66803(12) 0.65653(11) 0.0157(4) Uani 1 1 d . . .
H3A H 0.5898 0.7147 0.6813 0.019 Uiso 1 1 calc R . .
H3B H 0.5517 0.6652 0.5991 0.019 Uiso 1 1 calc R . .
C4 C 0.3377(2) 0.76240(12) 0.60164(10) 0.0147(4) Uani 1 1 d . . .
H4 H 0.4127 0.8067 0.5888 0.018 Uiso 1 1 calc R . .
C5 C 0.2137(2) 0.81720(13) 0.63369(11) 0.0202(4) Uani 1 1 d . . .
H5A H 0.1401 0.7741 0.6468 0.030 Uiso 1 1 calc R . .
H5B H 0.1823 0.8607 0.5930 0.030 Uiso 1 1 calc R . .
H5C H 0.2404 0.8514 0.6815 0.030 Uiso 1 1 calc R . .
C10 C 0.3008(2) 0.70697(12) 0.52556(10) 0.0148(4) Uani 1 1 d . . .
C11 C 0.1989(2) 0.63681(12) 0.52794(10) 0.0155(4) Uani 1 1 d . . .
H11 H 0.1556 0.6224 0.5769 0.019 Uiso 1 1 calc R . .
C12 C 0.1615(2) 0.58833(13) 0.45802(11) 0.0182(4) Uani 1 1 d . . .
H12 H 0.0921 0.5427 0.4601 0.022 Uiso 1 1 calc R . .
C13 C 0.2275(2) 0.60785(15) 0.38493(11) 0.0207(4) Uani 1 1 d . . .
H13 H 0.2034 0.5750 0.3382 0.025 Uiso 1 1 calc R . .
C14 C 0.3292(2) 0.67630(15) 0.38219(11) 0.0232(4) Uani 1 1 d . . .
H14 H 0.3735 0.6895 0.3333 0.028 Uiso 1 1 calc R . .
C15 C 0.3660(2) 0.72597(14) 0.45203(11) 0.0207(4) Uani 1 1 d . . .
H15 H 0.4346 0.7721 0.4494 0.025 Uiso 1 1 calc R . .
C20 C 0.6993(2) 0.53297(11) 0.66613(11) 0.0147(3) Uani 1 1 d . . .
C21 C 0.7122(2) 0.51340(13) 0.58317(11) 0.0191(4) Uani 1 1 d . . .
H21 H 0.6373 0.5241 0.5487 0.023 Uiso 1 1 calc R . .
C23 C 0.8356(2) 0.47818(14) 0.55171(13) 0.0247(5) Uani 1 1 d . . .
H23 H 0.8424 0.4649 0.4966 0.030 Uiso 1 1 calc R . .
C24 C 0.9483(2) 0.46280(14) 0.60193(13) 0.0264(5) Uani 1 1 d . . .
H24 H 1.0304 0.4385 0.5808 0.032 Uiso 1 1 calc R . .
C25 C 0.9382(2) 0.48384(13) 0.68409(13) 0.0253(4) Uani 1 1 d . . .
H25 H 1.0143 0.4747 0.7180 0.030 Uiso 1 1 calc R . .
C26 C 0.8141(2) 0.51867(13) 0.71570(12) 0.0195(4) Uani 1 1 d . . .
H26 H 0.8080 0.5325 0.7708 0.023 Uiso 1 1 calc R . .
C30 C 0.4592(2) 0.36455(12) 0.56334(10) 0.0149(4) Uani 1 1 d . . .
C31 C 0.3712(2) 0.40036(14) 0.50442(11) 0.0201(4) Uani 1 1 d . . .
H31 H 0.3006 0.4420 0.5185 0.024 Uiso 1 1 calc R . .
C32 C 0.3897(2) 0.37341(14) 0.42422(11) 0.0213(4) Uani 1 1 d . . .
H32 H 0.3311 0.3975 0.3844 0.026 Uiso 1 1 calc R . .
C33 C 0.4948(2) 0.31080(13) 0.40238(11) 0.0184(4) Uani 1 1 d . . .
C34 C 0.5835(2) 0.27677(13) 0.46297(11) 0.0207(4) Uani 1 1 d . . .
H34 H 0.6549 0.2356 0.4491 0.025 Uiso 1 1 calc R . .
C35 C 0.5664(2) 0.30360(12) 0.54367(10) 0.0188(4) Uani 1 1 d . . .
H35 H 0.6259 0.2809 0.5836 0.023 Uiso 1 1 calc R . .
C36 C 0.5098(3) 0.27832(14) 0.31542(11) 0.0248(5) Uani 1 1 d . . .
H36A H 0.6033 0.2573 0.3062 0.037 Uiso 1 1 calc R . .
H36B H 0.4890 0.3297 0.2795 0.037 Uiso 1 1 calc R . .
H36C H 0.4466 0.2273 0.3053 0.037 Uiso 1 1 calc R . .
N1 N 0.44149(17) 0.51044(10) 0.67286(9) 0.0147(3) Uani 1 1 d . . .
H1 H 0.3670 0.5410 0.6611 0.018 Uiso 1 1 calc R . .
N2 N 0.38548(16) 0.69735(11) 0.66628(9) 0.0151(3) Uani 1 1 d . . .
H2 H 0.3334 0.6788 0.7056 0.018 Uiso 1 1 calc R . .
O1 O 0.53165(17) 0.35309(9) 0.71505(7) 0.0207(3) Uani 1 1 d . . .
O2 O 0.28250(16) 0.37877(9) 0.67976(8) 0.0214(3) Uani 1 1 d . . .
F1 F 0.64380(14) 0.64733(8) 0.81585(6) 0.0237(3) Uani 1 1 d . . .
F2 F 0.58219(13) 0.50212(7) 0.82982(6) 0.0204(2) Uani 1 1 d . . .
F3 F 0.42747(14) 0.60911(8) 0.81460(6) 0.0226(2) Uani 1 1 d . . .
S1 S 0.42722(5) 0.39679(3) 0.66557(2) 0.01456(10) 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 0.0185(11) 0.0169(8) 0.0149(8) -0.0017(6) 0.0002(7) -0.0007(7)
C2 0.0144(10) 0.0138(7) 0.0126(7) -0.0006(5) 0.0001(7) -0.0012(7)
C3 0.0151(10) 0.0142(8) 0.0179(8) 0.0005(6) -0.0004(7) -0.0017(7)
C4 0.0145(10) 0.0128(8) 0.0168(8) 0.0008(6) -0.0001(7) -0.0004(7)
C5 0.0199(11) 0.0180(9) 0.0228(9) -0.0043(7) -0.0020(8) 0.0041(8)
C10 0.0152(10) 0.0145(8) 0.0147(8) 0.0018(6) -0.0008(7) 0.0009(7)
C11 0.0153(10) 0.0165(8) 0.0148(8) 0.0024(6) 0.0004(7) 0.0014(7)
C12 0.0189(11) 0.0159(8) 0.0200(8) 0.0005(6) -0.0044(8) -0.0007(7)
C13 0.0224(11) 0.0247(10) 0.0151(8) -0.0012(7) -0.0043(7) 0.0056(9)
C14 0.0230(12) 0.0326(11) 0.0140(8) 0.0041(7) 0.0021(8) 0.0025(9)
C15 0.0202(11) 0.0236(9) 0.0184(9) 0.0040(7) 0.0011(8) -0.0027(8)
C20 0.0142(9) 0.0121(8) 0.0177(8) 0.0012(6) 0.0031(7) -0.0015(6)
C21 0.0178(11) 0.0186(9) 0.0208(9) 0.0006(7) 0.0034(8) -0.0017(8)
C23 0.0250(12) 0.0239(10) 0.0250(10) -0.0029(7) 0.0105(9) -0.0020(9)
C24 0.0192(12) 0.0216(10) 0.0385(11) 0.0036(8) 0.0132(10) 0.0019(8)
C25 0.0171(11) 0.0230(9) 0.0357(10) 0.0063(8) -0.0011(9) 0.0022(9)
C26 0.0171(11) 0.0182(8) 0.0231(9) 0.0031(7) 0.0013(8) -0.0019(8)
C30 0.0182(11) 0.0133(8) 0.0132(7) -0.0012(6) 0.0002(7) -0.0014(7)
C31 0.0225(11) 0.0193(9) 0.0184(8) -0.0007(7) 0.0002(7) 0.0059(8)
C32 0.0242(12) 0.0235(10) 0.0163(8) 0.0000(7) -0.0046(7) 0.0048(8)
C33 0.0246(12) 0.0152(8) 0.0154(8) -0.0011(6) -0.0003(7) -0.0015(8)
C34 0.0217(11) 0.0180(9) 0.0226(9) -0.0025(6) 0.0005(9) 0.0055(8)
C35 0.0206(10) 0.0170(8) 0.0188(8) 0.0004(6) -0.0038(8) 0.0031(8)
C36 0.0327(13) 0.0239(10) 0.0177(9) -0.0033(7) 0.0006(8) 0.0007(9)
N1 0.0122(8) 0.0130(6) 0.0190(7) -0.0020(5) -0.0019(6) -0.0006(6)
N2 0.0149(8) 0.0170(7) 0.0135(6) 0.0009(6) 0.0007(6) 0.0000(6)
O1 0.0304(9) 0.0155(6) 0.0161(6) 0.0027(5) -0.0046(6) 0.0003(6)
O2 0.0234(8) 0.0211(7) 0.0197(6) -0.0025(5) 0.0035(6) -0.0078(6)
F1 0.0301(8) 0.0206(6) 0.0204(5) -0.0064(4) -0.0047(5) -0.0046(5)
F2 0.0254(7) 0.0213(5) 0.0144(5) 0.0029(4) -0.0018(5) 0.0017(5)
F3 0.0214(6) 0.0292(6) 0.0171(5) -0.0012(4) 0.0039(5) 0.0051(6)
S1 0.0188(2) 0.01269(18) 0.01224(17) 0.00024(15) -0.00012(17) -0.00205(17)
 
_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 F2 1.333(2) . ?
C1 F1 1.341(2) . ?
C1 F3 1.348(2) . ?
C1 C2 1.554(2) . ?
C2 N1 1.455(2) . ?
C2 C20 1.532(3) . ?
C2 C3 1.562(2) . ?
C3 N2 1.457(3) . ?
C4 N2 1.482(2) . ?
C4 C5 1.519(3) . ?
C4 C10 1.521(2) . ?
C10 C15 1.391(2) . ?
C10 C11 1.397(3) . ?
C11 C12 1.389(2) . ?
C12 C13 1.390(3) . ?
C13 C14 1.379(3) . ?
C14 C15 1.395(3) . ?
C20 C26 1.389(3) . ?
C20 C21 1.400(3) . ?
C21 C23 1.389(3) . ?
C23 C24 1.381(3) . ?
C24 C25 1.389(3) . ?
C25 C26 1.394(3) . ?
C30 C35 1.384(3) . ?
C30 C31 1.385(3) . ?
C30 S1 1.7720(17) . ?
C31 C32 1.387(2) . ?
C32 C33 1.393(3) . ?
C33 C34 1.399(3) . ?
C33 C36 1.512(2) . ?
C34 C35 1.393(2) . ?
N1 S1 1.6215(14) . ?
O1 S1 1.4348(14) . ?
O2 S1 1.4355(15) . ?
 
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
F2 C1 F1 107.37(15) . . ?
F2 C1 F3 105.95(15) . . ?
F1 C1 F3 106.30(14) . . ?
F2 C1 C2 113.49(14) . . ?
F1 C1 C2 112.28(15) . . ?
F3 C1 C2 110.98(16) . . ?
N1 C2 C20 113.91(14) . . ?
N1 C2 C1 107.50(15) . . ?
C20 C2 C1 112.10(16) . . ?
N1 C2 C3 105.63(15) . . ?
C20 C2 C3 109.21(14) . . ?
C1 C2 C3 108.15(14) . . ?
N2 C3 C2 112.26(15) . . ?
N2 C4 C5 108.20(14) . . ?
N2 C4 C10 110.06(14) . . ?
C5 C4 C10 111.51(16) . . ?
C15 C10 C11 118.64(17) . . ?
C15 C10 C4 120.78(17) . . ?
C11 C10 C4 120.58(16) . . ?
C12 C11 C10 120.72(17) . . ?
C11 C12 C13 120.10(18) . . ?
C14 C13 C12 119.56(17) . . ?
C13 C14 C15 120.58(18) . . ?
C10 C15 C14 120.38(19) . . ?
C26 C20 C21 118.31(19) . . ?
C26 C20 C2 124.44(17) . . ?
C21 C20 C2 117.25(17) . . ?
C23 C21 C20 120.8(2) . . ?
C24 C23 C21 120.32(19) . . ?
C23 C24 C25 119.7(2) . . ?
C24 C25 C26 120.0(2) . . ?
C20 C26 C25 120.94(19) . . ?
C35 C30 C31 121.38(16) . . ?
C35 C30 S1 120.87(14) . . ?
C31 C30 S1 117.73(15) . . ?
C30 C31 C32 119.23(19) . . ?
C31 C32 C33 120.97(18) . . ?
C32 C33 C34 118.58(17) . . ?
C32 C33 C36 120.53(18) . . ?
C34 C33 C36 120.86(19) . . ?
C35 C34 C33 120.98(19) . . ?
C30 C35 C34 118.83(17) . . ?
C2 N1 S1 131.18(13) . . ?
C3 N2 C4 113.18(14) . . ?
O1 S1 O2 120.71(9) . . ?
O1 S1 N1 109.12(8) . . ?
O2 S1 N1 104.29(9) . . ?
O1 S1 C30 107.86(9) . . ?
O2 S1 C30 106.12(9) . . ?
N1 S1 C30 108.18(8) . . ?
 
_diffrn_measured_fraction_theta_max    0.955
_diffrn_reflns_theta_full              25.00
_diffrn_measured_fraction_theta_full   0.983
_refine_diff_density_max    0.459
_refine_diff_density_min   -0.456
_refine_diff_density_rms    0.058