# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2013


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#                                CCDC 
# 
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#  This CIF contains data from an original supplementary publication 
#  deposited with the CCDC, and may include chemical, crystal,   
#  experimental, refinement, atomic coordinates, 
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted. 
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data_try1
_database_code_depnum_ccdc_archive 'CCDC 910363'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H16 F3 N O4 S'
_chemical_formula_weight         291.29
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   P2(1)2(1)2(1)
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'
_cell_length_a                   10.706(2)
_cell_length_b                   14.746(3)
_cell_length_c                   16.870(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2663.3(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8397
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      30.44
_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.30
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1216
_exptl_absorpt_coefficient_mu    0.285
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8944
_exptl_absorpt_correction_T_max  0.9193
_exptl_absorpt_process_details   SADABS
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      100(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 APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            166854
_diffrn_reflns_av_R_equivalents  0.0696
_diffrn_reflns_av_sigmaI/netI    0.0191
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         3.57
_diffrn_reflns_theta_max         30.51
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        30.51
_diffrn_measured_fraction_theta_full 0.998
_reflns_number_total             8110
_reflns_number_gt                7699
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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^)+(0.0300P)^2^+0.6000P] 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   -0.03(3)
_refine_ls_number_reflns         8110
_refine_ls_number_parameters     325
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0262
_refine_ls_R_factor_gt           0.0242
_refine_ls_wR_factor_ref         0.0601
_refine_ls_wR_factor_gt          0.0594
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.053
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 1.15364(13) 0.92232(9) 0.60858(8) 0.0297(3) Uani 1 1 d . . .
H1B H 1.1204 0.9835 0.6001 0.045 Uiso 1 1 calc R . .
H1C H 1.1836 0.8976 0.5581 0.045 Uiso 1 1 calc R . .
H1D H 1.2230 0.9250 0.6464 0.045 Uiso 1 1 calc R . .
C2 C 1.09204(10) 0.77908(7) 0.65395(6) 0.01568(18) Uani 1 1 d . . .
C3 C 0.98347(10) 0.72110(7) 0.68349(6) 0.01400(17) Uani 1 1 d . . .
H3A H 0.9199 0.7185 0.6401 0.017 Uiso 1 1 calc R . .
C4 C 0.92157(10) 0.76692(7) 0.75544(6) 0.01437(18) Uani 1 1 d . . .
H4B H 0.8884 0.8267 0.7371 0.017 Uiso 1 1 calc R . .
C5 C 1.15381(11) 0.89828(9) 0.90080(7) 0.0226(2) Uani 1 1 d . . .
C6 C 1.22634(13) 0.91197(11) 0.82409(8) 0.0332(3) Uani 1 1 d . . .
H6B H 1.3143 0.9239 0.8364 0.050 Uiso 1 1 calc R . .
H6C H 1.1914 0.9636 0.7951 0.050 Uiso 1 1 calc R . .
H6D H 1.2200 0.8572 0.7914 0.050 Uiso 1 1 calc R . .
C7 C 1.20578(13) 0.82151(11) 0.95130(8) 0.0312(3) Uani 1 1 d . . .
H7A H 1.2932 0.8342 0.9644 0.047 Uiso 1 1 calc R . .
H7B H 1.2005 0.7644 0.9218 0.047 Uiso 1 1 calc R . .
H7C H 1.1570 0.8165 1.0003 0.047 Uiso 1 1 calc R . .
C8 C 0.81076(11) 0.71187(9) 0.78556(7) 0.0227(2) Uani 1 1 d . . .
C9 C 1.14868(14) 0.98712(11) 0.94746(10) 0.0358(3) Uani 1 1 d . . .
H9A H 1.2333 1.0044 0.9637 0.054 Uiso 1 1 calc R . .
H9B H 1.0964 0.9790 0.9946 0.054 Uiso 1 1 calc R . .
H9C H 1.1131 1.0349 0.9140 0.054 Uiso 1 1 calc R . .
C10 C 0.95727(13) 0.83644(11) 1.14604(8) 0.0341(3) Uani 1 1 d . . .
H10A H 1.0429 0.8219 1.1622 0.051 Uiso 1 1 calc R . .
H10B H 0.9544 0.8452 1.0885 0.051 Uiso 1 1 calc R . .
H10C H 0.9017 0.7865 1.1609 0.051 Uiso 1 1 calc R . .
C11 C 0.91517(10) 0.92277(9) 1.18721(7) 0.0222(2) Uani 1 1 d . . .
C12 C 0.68276(9) 1.01920(7) 1.02046(6) 0.01419(18) Uani 1 1 d . . .
H12A H 0.6361 1.0545 1.0615 0.017 Uiso 1 1 calc R . .
C14 C 0.74722(10) 1.08837(7) 0.96557(6) 0.01457(17) Uani 1 1 d . . .
H14A H 0.6822 1.1192 0.9326 0.017 Uiso 1 1 calc R . .
C15 C 0.80854(10) 1.15853(7) 1.01961(7) 0.0180(2) Uani 1 1 d . . .
C16 C 0.99375(14) 1.23049(10) 1.05915(9) 0.0343(3) Uani 1 1 d . . .
H16A H 1.0834 1.2305 1.0475 0.051 Uiso 1 1 calc R . .
H16B H 0.9806 1.2148 1.1150 0.051 Uiso 1 1 calc R . .
H16C H 0.9593 1.2909 1.0487 0.051 Uiso 1 1 calc R . .
C17 C 0.99771(14) 1.00462(12) 1.16994(9) 0.0407(4) Uani 1 1 d . . .
H17A H 1.0841 0.9908 1.1849 0.061 Uiso 1 1 calc R . .
H17B H 0.9680 1.0568 1.2006 0.061 Uiso 1 1 calc R . .
H17C H 0.9941 1.0189 1.1132 0.061 Uiso 1 1 calc R . .
C18 C 0.58767(10) 0.96024(8) 0.97703(7) 0.0185(2) Uani 1 1 d . . .
C19 C 0.90566(13) 0.90813(10) 1.27693(7) 0.0281(3) Uani 1 1 d . . .
H19A H 0.9880 0.8918 1.2980 0.042 Uiso 1 1 calc R . .
H19B H 0.8463 0.8591 1.2879 0.042 Uiso 1 1 calc R . .
H19C H 0.8766 0.9641 1.3023 0.042 Uiso 1 1 calc R . .
F1 F 0.84425(8) 0.63895(6) 0.82747(5) 0.03541(19) Uani 1 1 d . . .
F2 F 0.73893(7) 0.76240(6) 0.83322(5) 0.03589(19) Uani 1 1 d . . .
F3 F 0.73788(8) 0.68243(6) 0.72620(5) 0.03294(18) Uani 1 1 d . . .
F4 F 0.52721(7) 0.90600(5) 1.02806(5) 0.02653(16) Uani 1 1 d . . .
F5 F 0.49970(7) 1.01301(5) 0.94263(4) 0.02467(15) Uani 1 1 d . . .
F6 F 0.63597(7) 0.90808(5) 0.92098(5) 0.02815(16) Uani 1 1 d . . .
N1 N 1.01115(9) 0.78516(6) 0.81794(5) 0.01560(16) Uani 1 1 d . . .
H1A H 1.0759 0.7494 0.8253 0.019 Uiso 1 1 calc R . .
N2 N 0.77486(8) 0.96486(6) 1.06166(5) 0.01481(16) Uani 1 1 d . . .
H2B H 0.8382 0.9399 1.0366 0.018 Uiso 1 1 calc R . .
O1 O 1.05612(8) 0.86450(6) 0.63981(5) 0.02129(17) Uani 1 1 d . . .
O2 O 1.02379(7) 0.63174(5) 0.69815(4) 0.01704(14) Uani 1 1 d . . .
H2A H 1.0729 0.6315 0.7370 0.026 Uiso 1 1 calc R . .
O3 O 1.19589(8) 0.75116(6) 0.64221(5) 0.02315(17) Uani 1 1 d . . .
O4 O 0.92915(8) 0.84922(6) 0.95216(5) 0.02135(17) Uani 1 1 d . . .
O5 O 0.93156(8) 1.16450(6) 1.00926(6) 0.02292(17) Uani 1 1 d . . .
O6 O 0.68042(8) 0.86865(6) 1.17693(5) 0.01973(16) Uani 1 1 d . . .
O7 O 0.74954(10) 1.20373(6) 1.06577(6) 0.0301(2) Uani 1 1 d . . .
O8 O 0.82855(8) 1.04142(6) 0.91563(5) 0.01797(15) Uani 1 1 d . . .
H8A H 0.8650 1.0783 0.8856 0.027 Uiso 1 1 calc R . .
S1 S 0.98840(2) 0.875807(17) 0.875681(15) 0.01579(5) Uani 1 1 d . . .
S2 S 0.75501(2) 0.952062(17) 1.157849(14) 0.01501(5) 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 0.0318(6) 0.0254(6) 0.0319(7) 0.0110(5) -0.0028(5) -0.0116(5)
C2 0.0195(4) 0.0171(5) 0.0105(4) -0.0001(4) -0.0009(4) -0.0009(4)
C3 0.0162(4) 0.0129(4) 0.0129(4) -0.0004(3) 0.0000(4) 0.0007(4)
C4 0.0135(4) 0.0143(4) 0.0153(4) -0.0011(4) 0.0002(3) -0.0008(3)
C5 0.0203(5) 0.0280(6) 0.0196(5) -0.0097(4) -0.0010(4) -0.0025(4)
C6 0.0268(6) 0.0464(8) 0.0265(6) -0.0074(6) 0.0037(5) -0.0137(6)
C7 0.0234(6) 0.0445(8) 0.0256(6) -0.0067(6) -0.0065(5) 0.0083(5)
C8 0.0202(5) 0.0249(6) 0.0230(5) -0.0045(4) 0.0049(4) -0.0059(4)
C9 0.0310(7) 0.0363(7) 0.0400(8) -0.0225(6) -0.0040(6) -0.0046(6)
C10 0.0273(6) 0.0534(9) 0.0215(6) -0.0015(6) -0.0034(5) 0.0172(6)
C11 0.0154(5) 0.0366(6) 0.0147(5) 0.0040(4) -0.0017(4) -0.0042(4)
C12 0.0134(4) 0.0146(4) 0.0145(4) 0.0007(3) 0.0010(3) -0.0003(3)
C14 0.0155(4) 0.0132(4) 0.0150(4) 0.0009(3) 0.0014(4) 0.0001(4)
C15 0.0191(5) 0.0148(5) 0.0200(5) 0.0007(4) 0.0001(4) -0.0022(4)
C16 0.0309(7) 0.0294(6) 0.0426(8) -0.0043(6) -0.0066(6) -0.0143(6)
C17 0.0285(7) 0.0627(10) 0.0310(7) 0.0123(6) -0.0069(6) -0.0249(7)
C18 0.0153(4) 0.0204(5) 0.0199(5) 0.0009(4) -0.0013(4) -0.0028(4)
C19 0.0269(6) 0.0431(7) 0.0142(5) 0.0033(5) -0.0025(4) -0.0036(5)
F1 0.0427(5) 0.0297(4) 0.0339(4) 0.0107(3) 0.0085(4) -0.0101(4)
F2 0.0229(4) 0.0423(5) 0.0425(5) -0.0163(4) 0.0161(4) -0.0076(3)
F3 0.0245(4) 0.0430(4) 0.0314(4) -0.0085(3) -0.0003(3) -0.0157(3)
F4 0.0237(3) 0.0270(4) 0.0289(4) 0.0068(3) -0.0020(3) -0.0115(3)
F5 0.0179(3) 0.0313(4) 0.0248(3) 0.0046(3) -0.0058(3) -0.0011(3)
F6 0.0272(4) 0.0271(4) 0.0302(4) -0.0132(3) 0.0006(3) -0.0043(3)
N1 0.0158(4) 0.0155(4) 0.0155(4) -0.0042(3) -0.0022(3) 0.0028(3)
N2 0.0156(4) 0.0173(4) 0.0115(4) 0.0012(3) 0.0017(3) 0.0011(3)
O1 0.0214(4) 0.0165(4) 0.0260(4) 0.0062(3) -0.0019(3) -0.0028(3)
O2 0.0219(4) 0.0126(3) 0.0166(3) -0.0005(3) -0.0015(3) 0.0026(3)
O3 0.0198(4) 0.0250(4) 0.0246(4) -0.0006(3) 0.0054(3) 0.0009(3)
O4 0.0254(4) 0.0229(4) 0.0158(4) -0.0014(3) 0.0051(3) 0.0035(3)
O5 0.0184(4) 0.0222(4) 0.0281(4) -0.0015(3) 0.0003(3) -0.0054(3)
O6 0.0203(4) 0.0213(4) 0.0176(4) 0.0042(3) 0.0024(3) -0.0064(3)
O7 0.0283(4) 0.0274(4) 0.0347(5) -0.0150(4) 0.0068(4) -0.0034(4)
O8 0.0225(4) 0.0140(3) 0.0173(3) 0.0007(3) 0.0073(3) 0.0001(3)
S1 0.01787(11) 0.01548(10) 0.01403(10) -0.00338(9) 0.00108(9) 0.00098(9)
S2 0.01615(10) 0.01687(10) 0.01202(10) 0.00039(8) 0.00215(9) -0.00286(9)
_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 O1 1.4473(15) . ?
C2 O3 1.2020(14) . ?
C2 O1 1.3384(13) . ?
C2 C3 1.5266(15) . ?
C3 O2 1.4084(12) . ?
C3 C4 1.5393(14) . ?
C4 N1 1.4505(13) . ?
C4 C8 1.5247(16) . ?
C5 C6 1.5226(18) . ?
C5 C7 1.5222(19) . ?
C5 C9 1.5293(18) . ?
C5 S1 1.8508(13) . ?
C8 F1 1.3359(16) . ?
C8 F3 1.3417(14) . ?
C8 F2 1.3390(14) . ?
C10 C11 1.519(2) . ?
C11 C17 1.5240(19) . ?
C11 C19 1.5323(17) . ?
C11 S2 1.8364(12) . ?
C12 N2 1.4483(13) . ?
C12 C18 1.5261(15) . ?
C12 C14 1.5408(14) . ?
C14 O8 1.3954(12) . ?
C14 C15 1.5272(15) . ?
C15 O7 1.2040(15) . ?
C15 O5 1.3316(14) . ?
C16 O5 1.4487(15) . ?
C18 F6 1.3241(13) . ?
C18 F4 1.3415(13) . ?
C18 F5 1.3526(13) . ?
N1 S1 1.6717(9) . ?
N2 S2 1.6473(10) . ?
O4 S1 1.4903(9) . ?
O6 S2 1.5013(9) . ?
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
O3 C2 O1 123.97(10) . . ?
O3 C2 C3 124.49(10) . . ?
O1 C2 C3 111.50(9) . . ?
O2 C3 C2 110.36(8) . . ?
O2 C3 C4 113.84(8) . . ?
C2 C3 C4 109.83(8) . . ?
N1 C4 C8 111.78(9) . . ?
N1 C4 C3 111.72(9) . . ?
C8 C4 C3 111.35(9) . . ?
C6 C5 C7 112.82(11) . . ?
C6 C5 C9 110.01(12) . . ?
C7 C5 C9 111.23(11) . . ?
C6 C5 S1 108.49(9) . . ?
C7 C5 S1 110.16(9) . . ?
C9 C5 S1 103.70(9) . . ?
F1 C8 F3 106.90(10) . . ?
F1 C8 F2 106.51(10) . . ?
F3 C8 F2 107.11(10) . . ?
F1 C8 C4 113.34(10) . . ?
F3 C8 C4 112.09(10) . . ?
F2 C8 C4 110.53(10) . . ?
C10 C11 C17 113.85(12) . . ?
C10 C11 C19 110.69(11) . . ?
C17 C11 C19 109.82(11) . . ?
C10 C11 S2 110.54(9) . . ?
C17 C11 S2 107.68(10) . . ?
C19 C11 S2 103.74(8) . . ?
N2 C12 C18 111.67(9) . . ?
N2 C12 C14 110.47(9) . . ?
C18 C12 C14 112.80(9) . . ?
O8 C14 C15 115.36(9) . . ?
O8 C14 C12 108.29(8) . . ?
C15 C14 C12 106.39(8) . . ?
O7 C15 O5 124.55(11) . . ?
O7 C15 C14 122.39(10) . . ?
O5 C15 C14 113.06(10) . . ?
F6 C18 F4 107.48(10) . . ?
F6 C18 F5 107.44(9) . . ?
F4 C18 F5 106.40(9) . . ?
F6 C18 C12 114.41(9) . . ?
F4 C18 C12 110.71(9) . . ?
F5 C18 C12 110.04(9) . . ?
C4 N1 S1 118.39(7) . . ?
C12 N2 S2 116.63(7) . . ?
C2 O1 C1 114.33(10) . . ?
C15 O5 C16 115.01(10) . . ?
O4 S1 N1 110.86(5) . . ?
O4 S1 C5 104.84(5) . . ?
N1 S1 C5 97.88(5) . . ?
O6 S2 N2 111.94(5) . . ?
O6 S2 C11 104.25(5) . . ?
N2 S2 C11 99.91(5) . . ?


data_try
_database_code_depnum_ccdc_archive 'CCDC 910364'
#TrackingRef 'web_deposit_cif_file_1_BassemS.Bassil_1352497403.compound_2.cif'
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H24 F3 N O6 S'
_chemical_formula_weight         391.40
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   P2(1)2(1)2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'-x+1/2, y+1/2, -z'
'x+1/2, -y+1/2, -z'
_cell_length_a                   25.049(2)
_cell_length_b                   8.4762(7)
_cell_length_c                   8.8991(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1889.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9703
_cell_measurement_theta_min      3.42
_cell_measurement_theta_max      28.05
_exptl_crystal_description       Block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9347
_exptl_absorpt_correction_T_max  0.9558
_exptl_absorpt_process_details   SADABS
_exptl_special_details           
;
?
;
_diffrn_ambient_temperature      100(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 APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            97622
_diffrn_reflns_av_R_equivalents  0.0541
_diffrn_reflns_av_sigmaI/netI    0.0197
_diffrn_reflns_limit_h_min       -33
_diffrn_reflns_limit_h_max       33
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.42
_diffrn_reflns_theta_max         28.43
_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        28.43
_diffrn_measured_fraction_theta_full 0.974
_reflns_number_total             4664
_reflns_number_gt                4491
_reflns_threshold_expression     >2sigma(I)
_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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^)+(0.0500P)^2^+3.2000P] 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   0.02(10)
_refine_ls_number_reflns         4664
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0477
_refine_ls_R_factor_gt           0.0455
_refine_ls_wR_factor_ref         0.1251
_refine_ls_wR_factor_gt          0.1237
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.063
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 0.69120(13) 0.0927(4) 0.6594(4) 0.0407(9) Uani 1 1 d . . .
H1A H 0.6892 -0.0115 0.6119 0.061 Uiso 1 1 calc R . .
H1B H 0.6666 0.0966 0.7450 0.061 Uiso 1 1 calc R . .
H1C H 0.7277 0.1116 0.6945 0.061 Uiso 1 1 calc R . .
C2 C 0.38493(13) 0.2441(6) -0.0783(4) 0.0490(11) Uani 1 1 d . . .
H2A H 0.3777 0.2952 -0.1750 0.073 Uiso 1 1 calc R . .
H2B H 0.3867 0.1295 -0.0925 0.073 Uiso 1 1 calc R . .
H2C H 0.4190 0.2822 -0.0384 0.073 Uiso 1 1 calc R . .
C3 C 0.67822(12) 0.3815(4) 0.6139(4) 0.0298(6) Uani 1 1 d . . .
H3A H 0.6679 0.4596 0.5381 0.045 Uiso 1 1 calc R . .
H3B H 0.7147 0.4033 0.6482 0.045 Uiso 1 1 calc R . .
H3C H 0.6537 0.3875 0.6994 0.045 Uiso 1 1 calc R . .
C4 C 0.33360(13) 0.4609(4) 0.0537(3) 0.0304(7) Uani 1 1 d . . .
H4A H 0.3257 0.5106 -0.0432 0.046 Uiso 1 1 calc R . .
H4B H 0.3666 0.5055 0.0948 0.046 Uiso 1 1 calc R . .
H4C H 0.3041 0.4806 0.1237 0.046 Uiso 1 1 calc R . .
C5 C 0.70879(11) 0.2032(4) 0.4045(3) 0.0290(6) Uani 1 1 d . . .
H5A H 0.6981 0.2851 0.3328 0.044 Uiso 1 1 calc R . .
H5B H 0.7029 0.0990 0.3598 0.044 Uiso 1 1 calc R . .
H5C H 0.7467 0.2156 0.4291 0.044 Uiso 1 1 calc R . .
C6 C 0.28777(12) 0.2081(5) -0.0169(4) 0.0382(8) Uani 1 1 d . . .
H6A H 0.2765 0.2535 -0.1131 0.057 Uiso 1 1 calc R . .
H6B H 0.2604 0.2285 0.0594 0.057 Uiso 1 1 calc R . .
H6C H 0.2927 0.0940 -0.0283 0.057 Uiso 1 1 calc R . .
C7 C 0.67585(10) 0.2184(3) 0.5461(3) 0.0209(5) Uani 1 1 d . . .
C8 C 0.52475(10) 0.2122(4) 0.1531(3) 0.0232(6) Uani 1 1 d . . .
C9 C 0.50608(9) 0.2644(3) 0.3093(3) 0.0173(5) Uani 1 1 d . . .
H9A H 0.5079 0.3820 0.3170 0.021 Uiso 1 1 calc R . .
C10 C 0.43830(10) 0.2397(3) 0.5166(3) 0.0203(5) Uani 1 1 d . . .
C11 C 0.59088(9) 0.2589(3) 0.4194(3) 0.0153(4) Uani 1 1 d . . .
C12 C 0.34043(10) 0.2833(4) 0.0317(3) 0.0255(6) Uani 1 1 d . . .
C13 C 0.44952(9) 0.2076(3) 0.3506(3) 0.0148(4) Uani 1 1 d . . .
H13A H 0.4474 0.0913 0.3327 0.018 Uiso 1 1 calc R . .
C14 C 0.53217(15) 0.2790(7) -0.1008(4) 0.0625(15) Uani 1 1 d . . .
H14A H 0.5228 0.3644 -0.1701 0.094 Uiso 1 1 calc R . .
H14B H 0.5149 0.1810 -0.1336 0.094 Uiso 1 1 calc R . .
H14C H 0.5710 0.2645 -0.1002 0.094 Uiso 1 1 calc R . .
N1 N 0.41128(8) 0.2861(2) 0.2529(2) 0.0145(4) Uani 1 1 d . . .
H1D H 0.4171 0.3814 0.2174 0.017 Uiso 1 1 calc R . .
O1 O 0.51398(9) 0.3189(4) 0.0502(3) 0.0442(7) Uani 1 1 d . . .
O2 O 0.54885(12) 0.0942(3) 0.1310(3) 0.0426(6) Uani 1 1 d . . .
O3 O 0.31087(7) 0.2298(3) 0.3117(2) 0.0282(5) Uani 1 1 d . . .
O4 O 0.60369(7) 0.3709(2) 0.3435(2) 0.0199(4) Uani 1 1 d . . .
O5 O 0.61903(7) 0.1750(2) 0.5135(2) 0.0222(4) Uani 1 1 d . . .
O6 O 0.54122(7) 0.1948(2) 0.4167(2) 0.0172(3) Uani 1 1 d . . .
F1 F 0.38623(6) 0.2338(2) 0.54596(18) 0.0302(4) Uani 1 1 d . . .
F2 F 0.45493(8) 0.3847(2) 0.5591(2) 0.0313(4) Uani 1 1 d . . .
F3 F 0.46202(7) 0.1366(2) 0.60814(19) 0.0267(4) Uani 1 1 d . . .
S1 S 0.35536(2) 0.18565(8) 0.21102(8) 0.02044(14) 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 0.0258(14) 0.042(2) 0.054(2) 0.0269(17) -0.0175(14) -0.0096(13)
C2 0.0246(15) 0.100(3) 0.0221(15) -0.0221(19) 0.0017(11) 0.0037(18)
C3 0.0219(12) 0.0353(17) 0.0323(15) -0.0121(13) -0.0047(11) -0.0026(11)
C4 0.0315(15) 0.0385(18) 0.0213(13) 0.0088(12) -0.0057(12) 0.0037(13)
C5 0.0193(12) 0.0337(17) 0.0341(15) -0.0066(13) -0.0019(11) 0.0042(12)
C6 0.0215(13) 0.064(3) 0.0294(15) -0.0169(16) -0.0114(11) -0.0018(15)
C7 0.0139(10) 0.0221(14) 0.0267(13) 0.0056(10) -0.0093(9) -0.0042(9)
C8 0.0170(11) 0.0267(15) 0.0259(12) 0.0072(11) -0.0034(10) -0.0080(10)
C9 0.0142(10) 0.0113(11) 0.0264(12) 0.0027(10) -0.0052(9) 0.0001(8)
C10 0.0189(11) 0.0202(13) 0.0218(12) -0.0031(10) -0.0032(9) 0.0022(10)
C11 0.0156(10) 0.0137(11) 0.0166(10) -0.0002(9) 0.0004(9) -0.0006(9)
C12 0.0165(11) 0.0404(18) 0.0196(12) -0.0089(12) -0.0048(9) 0.0012(11)
C13 0.0141(10) 0.0097(11) 0.0206(11) -0.0017(9) -0.0014(8) -0.0001(8)
C14 0.0365(18) 0.120(5) 0.0310(17) 0.040(2) 0.0000(14) 0.001(2)
N1 0.0141(8) 0.0095(10) 0.0198(10) -0.0013(7) -0.0035(7) 0.0003(7)
O1 0.0289(11) 0.0683(19) 0.0355(12) 0.0331(13) 0.0000(9) 0.0089(12)
O2 0.0696(17) 0.0298(13) 0.0285(11) 0.0049(10) 0.0161(12) 0.0100(12)
O3 0.0145(8) 0.0443(13) 0.0259(10) 0.0097(9) 0.0025(7) -0.0006(8)
O4 0.0177(8) 0.0146(9) 0.0276(10) 0.0042(7) -0.0034(7) -0.0012(7)
O5 0.0150(8) 0.0229(10) 0.0286(10) 0.0091(8) -0.0076(7) -0.0057(8)
O6 0.0142(7) 0.0130(8) 0.0245(9) 0.0055(7) -0.0045(6) -0.0016(7)
F1 0.0205(8) 0.0498(12) 0.0204(8) -0.0075(8) 0.0018(6) 0.0034(7)
F2 0.0437(10) 0.0221(9) 0.0282(9) -0.0095(7) -0.0105(8) 0.0010(8)
F3 0.0307(8) 0.0272(9) 0.0220(8) 0.0054(7) 0.0007(6) 0.0056(7)
S1 0.0136(2) 0.0168(3) 0.0309(3) -0.0031(3) -0.0035(2) -0.0015(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
C1 C7 1.517(4) . ?
C2 C12 1.521(4) . ?
C3 C7 1.509(4) . ?
C4 C12 1.528(5) . ?
C5 C7 1.512(4) . ?
C6 C12 1.528(4) . ?
C7 O5 1.499(3) . ?
C8 O2 1.184(4) . ?
C8 O1 1.315(3) . ?
C8 C9 1.532(4) . ?
C9 O6 1.427(3) . ?
C9 C13 1.541(3) . ?
C10 F3 1.334(3) . ?
C10 F1 1.331(3) . ?
C10 F2 1.352(3) . ?
C10 C13 1.528(4) . ?
C11 O4 1.209(3) . ?
C11 O5 1.305(3) . ?
C11 O6 1.357(3) . ?
C12 S1 1.836(3) . ?
C13 N1 1.455(3) . ?
C14 O1 1.459(5) . ?
N1 S1 1.681(2) . ?
O3 S1 1.478(2) . ?
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
O5 C7 C3 109.9(2) . . ?
O5 C7 C1 101.4(2) . . ?
C3 C7 C1 111.6(3) . . ?
O5 C7 C5 109.6(2) . . ?
C3 C7 C5 113.0(2) . . ?
C1 C7 C5 110.8(3) . . ?
O2 C8 O1 124.7(3) . . ?
O2 C8 C9 123.4(3) . . ?
O1 C8 C9 111.7(3) . . ?
O6 C9 C8 107.5(2) . . ?
O6 C9 C13 106.13(19) . . ?
C8 C9 C13 114.0(2) . . ?
F3 C10 F1 107.0(2) . . ?
F3 C10 F2 106.7(2) . . ?
F1 C10 F2 106.3(2) . . ?
F3 C10 C13 113.1(2) . . ?
F1 C10 C13 111.3(2) . . ?
F2 C10 C13 112.1(2) . . ?
O4 C11 O5 130.0(2) . . ?
O4 C11 O6 123.2(2) . . ?
O5 C11 O6 106.8(2) . . ?
C2 C12 C6 111.0(2) . . ?
C2 C12 C4 112.4(3) . . ?
C6 C12 C4 110.6(3) . . ?
C2 C12 S1 108.2(2) . . ?
C6 C12 S1 103.5(2) . . ?
C4 C12 S1 110.85(19) . . ?
N1 C13 C10 112.06(19) . . ?
N1 C13 C9 108.66(19) . . ?
C10 C13 C9 110.2(2) . . ?
C13 N1 S1 116.73(16) . . ?
C8 O1 C14 114.7(3) . . ?
C11 O5 C7 120.2(2) . . ?
C11 O6 C9 114.31(19) . . ?
O3 S1 N1 111.45(11) . . ?
O3 S1 C12 104.99(12) . . ?
N1 S1 C12 97.70(12) . . ?