data_global

_audit_creation_method            
;
manual editing of the CIF file 
created by SHELXTL Ver. 6.14
;

# 1. SUBMISSION DETAILS

_publ_contact_author_name
;
Welch, John T
;
_publ_contact_author_address
;
Department of Chemistry
University at Albany
1400 Washington ave
Albany NY 12222
USA
;

_publ_contact_author_phone    '518-442-4455'
_publ_contact_author_fax      '518-442-3462'
_publ_contact_author_email    jwelch@albany.edu

_publ_requested_journal      
;
 Bielstein Journal of Organic Chemistry
;


# 2. TITLE AND AUTHOR LIST

_publ_section_title
;
 Diastereoselectivity in the Staudinger Reaction of 
 Pentafluorosulfanyl Aldimines and Ketimines
;

loop_
_publ_author_name
_publ_author_address

;
'Penger, Alexander'
;
;
Department of Chemistry
University at Albany
1400 Washington ave
Albany NY 12222
USA
;

;
'Von Hahmann, Cortney N.'
;
;
Department of Chemistry
University at Albany
1400 Washington ave
Albany NY 12222
USA
;

;
'Filatov, Alexander S.'
;
;
Department of Chemistry
University at Albany
1400 Washington ave
Albany NY 12222
USA
;

;
'Welch, John, T.
;
;
Department of Chemistry
University at Albany
1400 Washington ave
Albany NY 12222
USA
;

data_7a 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 (3SR,4RS)-3-(benzyloxy)-4-(pentafluorosulfanylmethyl)-
 -1-(4-methoxyphenyl)azetidin-2-one 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          'C18 H18 F5 N O3 S' 
_chemical_formula_sum             'C18 H18 F5 N O3 S' 
_chemical_formula_weight          423.39 
 
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           'Monoclinic'
_symmetry_space_group_name_H-M    'P 1 21/c 1  '
_symmetry_space_group_name_Hall   '-P 2ybc     '
_symmetry_int_tables_number       14
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y-1/2, z-1/2' 
 
_cell_length_a                    5.9580(11) 
_cell_length_b                    14.455(3) 
_cell_length_c                    20.381(4) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  92.069(2) 
_cell_angle_gamma                 90.00 
_cell_volume                      1754.1(6) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     100(2) 
_cell_measurement_reflns_used     9899
_cell_measurement_theta_min       2.45
_cell_measurement_theta_max       28.18
 
_exptl_crystal_description        block
_exptl_crystal_colour             colorless
_exptl_crystal_size_max           0.46 
_exptl_crystal_size_mid           0.12 
_exptl_crystal_size_min           0.12 
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.603 
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              872 
_exptl_absorpt_coefficient_mu     0.257 
_exptl_absorpt_correction_type    'multi-scan'
_exptl_absorpt_process_details
;
SADABS  (Bruker-AXS, 2003)
;
_exptl_absorpt_correction_T_min   0.8911 
_exptl_absorpt_correction_T_max   0.9699 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       100(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            Mo-K\a
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Bruker SMART APEX CCD area-detector' 
_diffrn_measurement_method        '0.30° ω scans'
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             14943 
_diffrn_reflns_av_R_equivalents   0.0225 
_diffrn_reflns_av_sigmaI/netI     0.0182 
_diffrn_reflns_limit_h_min        -7 
_diffrn_reflns_limit_h_max        7 
_diffrn_reflns_limit_k_min        -18 
_diffrn_reflns_limit_k_max        18 
_diffrn_reflns_limit_l_min        -27 
_diffrn_reflns_limit_l_max        26 
_diffrn_reflns_theta_min          1.73 
_diffrn_reflns_theta_max          28.29 
_diffrn_measured_fraction_theta_max    0.944 
_diffrn_reflns_theta_full              25.00 
_diffrn_measured_fraction_theta_full   1.000 
_reflns_number_total              4102 
_reflns_number_gt                 3715 
_reflns_threshold_expression      I>2σ(I) 
 
_computing_data_collection        'SMART Ver. 5.622 (Bruker-AXS, 2003)'
_computing_cell_refinement        'SAINT Ver. 6.22  (Bruker-AXS, 2003)'
_computing_data_reduction         'SAINT Ver. 6.22'
_computing_structure_solution     'SHELXTL Ver. 6.14 (Bruker-AXS, 2003)'
_computing_structure_refinement   'SHELXTL Ver. 6.14'
_computing_molecular_graphics     'SHELXTL Ver. 6.14'
_computing_publication_material   'SHELXTL Ver. 6.14' 
 
_refine_special_details 
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0519P)²+0.6410P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    geom 
_refine_ls_hydrogen_treatment     refall
_refine_ls_extinction_method      none 
_refine_ls_extinction_coef        ? 
_refine_ls_number_reflns          4102 
_refine_ls_number_parameters      325 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0352 
_refine_ls_R_factor_gt            0.0322 
_refine_ls_wR_factor_ref          0.0898 
_refine_ls_wR_factor_gt           0.0867 
_refine_ls_goodness_of_fit_ref    1.059 
_refine_ls_restrained_S_all       1.059
_refine_diff_density_max          0.382 
_refine_diff_density_min         -0.408 
_refine_diff_density_rms          0.052  
_refine_ls_shift/su_max           0.001 
_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 
S1 S 0.25771(5) 0.58933(2) 0.070593(14) 0.01690(9) Uani 1 1 d . . . 
N1 N 0.60685(17) 0.82766(7) 0.03495(5) 0.0174(2) Uani 1 1 d . . . 
O1 O 0.95635(15) 0.87143(7) 0.08425(5) 0.0238(2) Uani 1 1 d . . . 
O2 O 0.74258(15) 0.69507(6) 0.15464(4) 0.01937(18) Uani 1 1 d . . . 
O3 O 0.42729(15) 1.01390(6) -0.20014(4) 0.02182(19) Uani 1 1 d . . . 
C1 C 0.4588(2) 0.96557(8) -0.14245(6) 0.0180(2) Uani 1 1 d . . . 
C2 C 0.3018(2) 0.90571(8) -0.11673(6) 0.0188(2) Uani 1 1 d . . . 
C3 C 0.3531(2) 0.86046(8) -0.05756(6) 0.0186(2) Uani 1 1 d . . . 
C4 C 0.7164(2) 0.93472(8) -0.05088(6) 0.0183(2) Uani 1 1 d . . . 
C5 C 0.6648(2) 0.98017(8) -0.10918(6) 0.0194(2) Uani 1 1 d . . . 
C6 C 0.5595(2) 0.87403(8) -0.02487(6) 0.0167(2) Uani 1 1 d . . . 
C7 C 0.4662(2) 0.66790(8) 0.03934(6) 0.0168(2) Uani 1 1 d . . . 
C8 C 0.46482(19) 0.76340(8) 0.07122(6) 0.0163(2) Uani 1 1 d . . . 
C9 C 0.7749(2) 0.83357(8) 0.08268(6) 0.0183(2) Uani 1 1 d . . . 
C10 C 0.6379(2) 0.77553(8) 0.13043(6) 0.0175(2) Uani 1 1 d . . . 
C11 C 0.7137(2) 0.67797(9) 0.22306(6) 0.0207(2) Uani 1 1 d . . . 
C12 C 0.8599(2) 0.73894(8) 0.26744(6) 0.0179(2) Uani 1 1 d . . . 
C13 C 0.8000(2) 0.75316(9) 0.33224(6) 0.0208(2) Uani 1 1 d . . . 
C14 C 0.9360(2) 0.80589(9) 0.37474(6) 0.0235(3) Uani 1 1 d . . . 
C15 C 1.1328(2) 0.84505(9) 0.35279(7) 0.0234(3) Uani 1 1 d . . . 
C16 C 1.1925(2) 0.83219(9) 0.28833(7) 0.0223(3) Uani 1 1 d . . . 
C17 C 1.0564(2) 0.77932(9) 0.24563(6) 0.0197(2) Uani 1 1 d . . . 
C18 C 0.2157(2) 1.00211(10) -0.23473(6) 0.0238(3) Uani 1 1 d . . . 
F1 F 0.05925(12) 0.65236(5) 0.04016(4) 0.02203(17) Uani 1 1 d . . . 
F2 F 0.25641(14) 0.52971(5) 0.00489(4) 0.02572(18) Uani 1 1 d . . . 
F3 F 0.07034(13) 0.52251(6) 0.09616(4) 0.02702(18) Uani 1 1 d . . . 
F4 F 0.44015(14) 0.52131(5) 0.10278(4) 0.02633(18) Uani 1 1 d . . . 
F5 F 0.24641(12) 0.64271(5) 0.13858(3) 0.02084(16) Uani 1 1 d . . . 
H2 H 0.166(3) 0.8933(11) -0.1381(8) 0.025(4) Uiso 1 1 d . . . 
H3 H 0.243(3) 0.8195(12) -0.0393(8) 0.026(4) Uiso 1 1 d . . . 
H4 H 0.853(3) 0.9457(11) -0.0293(8) 0.020(4) Uiso 1 1 d . . . 
H5 H 0.770(3) 1.0214(11) -0.1267(8) 0.023(4) Uiso 1 1 d . . . 
H8 H 0.310(3) 0.7862(11) 0.0773(7) 0.017(4) Uiso 1 1 d . . . 
H10 H 0.580(3) 0.8150(11) 0.1654(8) 0.022(4) Uiso 1 1 d . . . 
H13 H 0.670(3) 0.7262(12) 0.3463(8) 0.024(4) Uiso 1 1 d . . . 
H14 H 0.890(3) 0.8155(12) 0.4192(9) 0.032(4) Uiso 1 1 d . . . 
H15 H 1.226(3) 0.8813(12) 0.3805(8) 0.027(4) Uiso 1 1 d . . . 
H16 H 1.326(3) 0.8609(12) 0.2728(9) 0.030(4) Uiso 1 1 d . . . 
H17 H 1.094(3) 0.7724(11) 0.2017(8) 0.023(4) Uiso 1 1 d . . . 
H7A H 0.607(3) 0.6393(11) 0.0465(7) 0.019(4) Uiso 1 1 d . . . 
H11A H 0.753(2) 0.6143(11) 0.2292(7) 0.017(3) Uiso 1 1 d . . . 
H18A H 0.197(3) 0.9371(12) -0.2480(8) 0.026(4) Uiso 1 1 d . . . 
H7B H 0.432(3) 0.6732(11) -0.0080(8) 0.022(4) Uiso 1 1 d . . . 
H11B H 0.553(3) 0.6873(11) 0.2342(7) 0.021(4) Uiso 1 1 d . . . 
H18B H 0.091(3) 1.0226(11) -0.2080(8) 0.027(4) Uiso 1 1 d . . . 
H18C H 0.223(3) 1.0406(13) -0.2735(9) 0.031(4) Uiso 1 1 d . . . 
 
 
_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 F3 1.5788(8) . ? 
S1 F5 1.5894(8) . ? 
S1 F4 1.5897(8) . ? 
S1 F2 1.5923(8) . ? 
S1 F1 1.6000(8) . ? 
S1 C7 1.8155(12) . ? 
N1 C9 1.3731(15) . ? 
N1 C6 1.4108(15) . ? 
N1 C8 1.4733(15) . ? 
O1 C9 1.2112(15) . ? 
O2 C10 1.4011(14) . ? 
O2 C11 1.4326(15) . ? 
O3 C1 1.3747(14) . ? 
O3 C18 1.4324(16) . ? 
C1 C2 1.3908(17) . ? 
C1 C5 1.3967(17) . ? 
C2 C3 1.3961(17) . ? 
C2 H2 0.921(17) . ? 
C3 C6 1.3912(17) . ? 
C3 H3 0.968(17) . ? 
C4 C5 1.3826(18) . ? 
C4 C6 1.3998(16) . ? 
C4 H4 0.926(16) . ? 
C5 H5 0.946(17) . ? 
C7 C8 1.5258(16) . ? 
C7 H7A 0.942(16) . ? 
C7 H7B 0.982(16) . ? 
C8 C10 1.5686(16) . ? 
C8 H8 0.990(15) . ? 
C9 C10 1.5408(17) . ? 
C10 H10 0.984(16) . ? 
C11 C12 1.5154(17) . ? 
C11 H11A 0.958(16) . ? 
C11 H11B 1.002(16) . ? 
C12 C17 1.3951(17) . ? 
C12 C13 1.3957(18) . ? 
C13 C14 1.3920(18) . ? 
C13 H13 0.923(17) . ? 
C14 C15 1.390(2) . ? 
C14 H14 0.966(18) . ? 
C15 C16 1.3860(19) . ? 
C15 H15 0.939(17) . ? 
C16 C17 1.3957(17) . ? 
C16 H16 0.959(18) . ? 
C17 H17 0.937(16) . ? 
C18 H18A 0.983(18) . ? 
C18 H18B 0.982(18) . ? 
C18 H18C 0.969(18) . ? 
 
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 
F3 S1 F5 87.51(4) . . ? 
F3 S1 F4 88.08(5) . . ? 
F5 S1 F4 89.45(4) . . ? 
F3 S1 F2 87.97(4) . . ? 
F5 S1 F2 175.42(4) . . ? 
F4 S1 F2 89.70(5) . . ? 
F3 S1 F1 87.41(4) . . ? 
F5 S1 F1 90.43(4) . . ? 
F4 S1 F1 175.50(4) . . ? 
F2 S1 F1 90.06(4) . . ? 
F3 S1 C7 178.09(5) . . ? 
F5 S1 C7 93.05(5) . . ? 
F4 S1 C7 93.75(5) . . ? 
F2 S1 C7 91.50(5) . . ? 
F1 S1 C7 90.76(5) . . ? 
C9 N1 C6 134.47(10) . . ? 
C9 N1 C8 95.80(9) . . ? 
C6 N1 C8 129.25(10) . . ? 
C10 O2 C11 114.73(9) . . ? 
C1 O3 C18 116.81(10) . . ? 
O3 C1 C2 124.46(11) . . ? 
O3 C1 C5 115.40(11) . . ? 
C2 C1 C5 120.15(11) . . ? 
C1 C2 C3 119.18(11) . . ? 
C1 C2 H2 122.2(10) . . ? 
C3 C2 H2 118.6(10) . . ? 
C6 C3 C2 120.67(11) . . ? 
C6 C3 H3 120.1(10) . . ? 
C2 C3 H3 119.2(10) . . ? 
C5 C4 C6 119.50(11) . . ? 
C5 C4 H4 119.5(10) . . ? 
C6 C4 H4 121.0(10) . . ? 
C4 C5 C1 120.65(11) . . ? 
C4 C5 H5 119.6(10) . . ? 
C1 C5 H5 119.7(10) . . ? 
C3 C6 C4 119.84(11) . . ? 
C3 C6 N1 119.50(11) . . ? 
C4 C6 N1 120.65(10) . . ? 
C8 C7 S1 113.72(8) . . ? 
C8 C7 H7A 110.5(9) . . ? 
S1 C7 H7A 106.7(9) . . ? 
C8 C7 H7B 110.1(9) . . ? 
S1 C7 H7B 105.8(9) . . ? 
H7A C7 H7B 109.8(13) . . ? 
N1 C8 C7 110.17(10) . . ? 
N1 C8 C10 86.67(9) . . ? 
C7 C8 C10 114.53(10) . . ? 
N1 C8 H8 114.0(9) . . ? 
C7 C8 H8 112.0(9) . . ? 
C10 C8 H8 117.1(9) . . ? 
O1 C9 N1 132.38(12) . . ? 
O1 C9 C10 136.22(12) . . ? 
N1 C9 C10 91.39(9) . . ? 
O2 C10 C9 115.80(10) . . ? 
O2 C10 C8 116.74(10) . . ? 
C9 C10 C8 85.61(9) . . ? 
O2 C10 H10 112.9(9) . . ? 
C9 C10 H10 110.3(9) . . ? 
C8 C10 H10 112.7(9) . . ? 
O2 C11 C12 113.21(10) . . ? 
O2 C11 H11A 104.9(9) . . ? 
C12 C11 H11A 110.3(9) . . ? 
O2 C11 H11B 110.3(9) . . ? 
C12 C11 H11B 108.7(9) . . ? 
H11A C11 H11B 109.4(13) . . ? 
C17 C12 C13 119.08(11) . . ? 
C17 C12 C11 121.59(11) . . ? 
C13 C12 C11 119.30(11) . . ? 
C14 C13 C12 120.43(12) . . ? 
C14 C13 H13 121.0(10) . . ? 
C12 C13 H13 118.5(10) . . ? 
C15 C14 C13 120.11(12) . . ? 
C15 C14 H14 121.0(11) . . ? 
C13 C14 H14 118.9(11) . . ? 
C16 C15 C14 119.90(12) . . ? 
C16 C15 H15 118.6(11) . . ? 
C14 C15 H15 121.5(11) . . ? 
C15 C16 C17 120.09(12) . . ? 
C15 C16 H16 119.9(11) . . ? 
C17 C16 H16 120.0(11) . . ? 
C12 C17 C16 120.39(12) . . ? 
C12 C17 H17 119.6(10) . . ? 
C16 C17 H17 120.0(10) . . ? 
O3 C18 H18A 109.8(10) . . ? 
O3 C18 H18B 111.2(10) . . ? 
H18A C18 H18B 111.0(14) . . ? 
O3 C18 H18C 105.5(10) . . ? 
H18A C18 H18C 109.5(14) . . ? 
H18B C18 H18C 109.7(14) . . ? 

data_7c
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 (3SR,4RS)-3-(benzyloxy)-4-((1SR)-pentafluorosulfanyl-propyl)-
 -1-(4-methoxyphenyl)azetidin-2-one
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          'C20 H22 F5 N O3 S' 
_chemical_formula_sum             'C20 H22 F5 N O3 S' 
_chemical_formula_weight          451.45 
 
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' 
 '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' 
 'N'  'N'   0.0061   0.0033 
 '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        '
_symmetry_space_group_name_Hall   '-P 1        '
_symmetry_int_tables_number       2
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, -y, -z' 
 
_cell_length_a                    6.809(7) 
_cell_length_b                    10.145(10) 
_cell_length_c                    14.616(15) 
_cell_angle_alpha                 93.168(13) 
_cell_angle_beta                  95.116(14) 
_cell_angle_gamma                 97.126(13) 
_cell_volume                      995.6(18) 
_cell_formula_units_Z             2 
_cell_measurement_temperature     100(2) 
_cell_measurement_reflns_used     1663
_cell_measurement_theta_min       2.39
_cell_measurement_theta_max       24.43
 
_exptl_crystal_description        needle
_exptl_crystal_colour             colorless
_exptl_crystal_size_max           0.24 
_exptl_crystal_size_mid           0.10 
_exptl_crystal_size_min           0.08 
_exptl_crystal_density_meas       ?
_exptl_crystal_density_diffrn     1.506 
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000              468 
_exptl_absorpt_coefficient_mu     0.231 
_exptl_absorpt_correction_type    'multi-scan'
_exptl_absorpt_process_details
;
SADABS  (Bruker-AXS, 2003)
;
_exptl_absorpt_correction_T_min   0.9466 
_exptl_absorpt_correction_T_max   0.9817 
 
_exptl_special_details 
; 
 ? 
; 
 
_diffrn_ambient_temperature       100(2) 
_diffrn_radiation_wavelength      0.71073 
_diffrn_radiation_type            Mo-K\a
_diffrn_radiation_source          'fine-focus sealed tube' 
_diffrn_radiation_monochromator   graphite 
_diffrn_measurement_device_type   'Bruker SMART APEX CCD area-detector' 
_diffrn_measurement_method        '0.30° ω scans'
_diffrn_detector_area_resol_mean  ? 
_diffrn_reflns_number             6182 
_diffrn_reflns_av_R_equivalents   0.0721 
_diffrn_reflns_av_sigmaI/netI     0.1378 
_diffrn_reflns_limit_h_min        -8 
_diffrn_reflns_limit_h_max        8 
_diffrn_reflns_limit_k_min        -11 
_diffrn_reflns_limit_k_max        12 
_diffrn_reflns_limit_l_min        -17 
_diffrn_reflns_limit_l_max        17 
_diffrn_reflns_theta_min          2.03 
_diffrn_reflns_theta_max          25.17
_diffrn_measured_fraction_theta_max    0.949 
_diffrn_reflns_theta_full              25.17 
_diffrn_measured_fraction_theta_full   0.949 
_reflns_number_total              3390 
_reflns_number_gt                 1667 
_reflns_threshold_expression      I>2σ(I) 
 
_computing_data_collection        'SMART Ver. 5.622 (Bruker-AXS, 2003)'
_computing_cell_refinement        'SAINT Ver. 6.22  (Bruker-AXS, 2003)'
_computing_data_reduction         'SAINT Ver. 6.22'
_computing_structure_solution     'SHELXTL Ver. 6.14 (Bruker-AXS, 2003)'
_computing_structure_refinement   'SHELXTL Ver. 6.14'
_computing_molecular_graphics     'SHELXTL Ver. 6.14'
_computing_publication_material   'SHELXTL Ver. 6.14' 
 
_refine_special_details 
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0391P)²+17.3100P] where P=(Fo²+2Fc²)/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_number_reflns          3390 
_refine_ls_number_parameters      273 
_refine_ls_number_restraints      414 
_refine_ls_R_factor_all           0.2002 
_refine_ls_R_factor_gt            0.1262 
_refine_ls_wR_factor_ref          0.3241 
_refine_ls_wR_factor_gt           0.2922 
_refine_ls_goodness_of_fit_ref    1.051 
_refine_ls_restrained_S_all       1.037
_refine_diff_density_max          1.159 
_refine_diff_density_min         -0.956 
_refine_diff_density_rms          0.180   
_refine_ls_shift/su_max           0.000 
_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 
S1 S 0.3604(4) 0.2566(3) 0.3651(2) 0.0409(8) Uani 1 1 d U . . 
F1 F 0.3840(9) 0.3885(5) 0.3087(4) 0.0450(16) Uani 1 1 d U . . 
F5 F 0.1792(8) 0.1934(5) 0.2915(4) 0.0397(15) Uani 1 1 d U . . 
F2 F 0.5268(10) 0.3246(6) 0.4431(4) 0.0488(17) Uani 1 1 d U . . 
O2 O 0.3019(10) -0.0705(7) 0.2143(5) 0.0365(17) Uani 1 1 d U . . 
F4 F 0.3225(10) 0.1316(6) 0.4250(4) 0.0499(17) Uani 1 1 d U . . 
F3 F 0.2022(10) 0.3224(6) 0.4194(5) 0.0506(18) Uani 1 1 d U . . 
O4 O 1.3133(11) 0.4685(7) 0.0590(5) 0.0416(19) Uani 1 1 d U . . 
O1 O 0.6361(11) -0.0751(7) 0.0731(5) 0.0413(18) Uani 1 1 d U . . 
C2 C 1.1370(15) 0.3998(10) 0.0804(7) 0.034(2) Uani 1 1 d U . . 
N1 N 0.6408(12) 0.1431(8) 0.1433(6) 0.0323(19) Uani 1 1 d U . . 
C5 C 0.8106(15) 0.2279(10) 0.1188(7) 0.033(2) Uani 1 1 d U . . 
C12 C 0.0294(16) -0.2133(10) 0.2648(7) 0.034(2) Uani 1 1 d U . . 
C17 C -0.1752(17) -0.2551(10) 0.2639(8) 0.040(2) Uani 1 1 d U . . 
H17 H -0.2689 -0.2152 0.2261 0.048 Uiso 1 1 calc R . . 
C6 C 0.9455(15) 0.1810(10) 0.0666(7) 0.035(2) Uani 1 1 d U . . 
H6 H 0.9265 0.0901 0.0442 0.042 Uiso 1 1 calc R . . 
C9 C 0.4807(15) 0.1684(10) 0.1989(7) 0.031(2) Uani 1 1 d U . . 
H9 H 0.4106 0.2433 0.1767 0.038 Uiso 1 1 calc R . . 
C10 C 0.3728(16) 0.0274(10) 0.1557(7) 0.034(2) Uani 1 1 d U . . 
H10 H 0.2670 0.0391 0.1059 0.041 Uiso 1 1 calc R . . 
C7 C 1.1121(16) 0.2646(10) 0.0453(7) 0.034(2) Uani 1 1 d U . . 
H7 H 1.2061 0.2320 0.0085 0.041 Uiso 1 1 calc R . . 
C11 C 0.0881(15) -0.1024(10) 0.2026(7) 0.035(2) Uani 1 1 d U . . 
H11A H 0.0432 -0.1319 0.1376 0.042 Uiso 1 1 calc R . . 
H11B H 0.0248 -0.0229 0.2193 0.042 Uiso 1 1 calc R . . 
C8 C 0.5678(16) 0.0111(10) 0.1154(7) 0.034(2) Uani 1 1 d U . . 
C4 C 0.8314(16) 0.3637(10) 0.1506(7) 0.034(2) Uani 1 1 d U . . 
H4 H 0.7338 0.3978 0.1844 0.041 Uiso 1 1 calc R . . 
C3 C 1.0018(15) 0.4466(10) 0.1306(7) 0.035(2) Uani 1 1 d U . . 
H3 H 1.0213 0.5374 0.1530 0.042 Uiso 1 1 calc R . . 
C13 C 0.1622(17) -0.2681(10) 0.3213(7) 0.037(2) Uani 1 1 d U . . 
H13 H 0.3001 -0.2370 0.3235 0.045 Uiso 1 1 calc R . . 
C1 C 1.3499(17) 0.6080(10) 0.0917(8) 0.040(3) Uani 1 1 d U . . 
H1A H 1.2371 0.6530 0.0698 0.059 Uiso 1 1 calc R . . 
H1B H 1.4712 0.6500 0.0683 0.059 Uiso 1 1 calc R . . 
H1C H 1.3661 0.6152 0.1592 0.059 Uiso 1 1 calc R . . 
C18 C 0.5494(15) 0.1884(9) 0.3011(7) 0.032(2) Uani 1 1 d U . . 
H18 H 0.6624 0.2622 0.3055 0.039 Uiso 1 1 calc R . . 
C14 C 0.0964(17) -0.3705(11) 0.3765(8) 0.043(3) Uani 1 1 d U . . 
H14 H 0.1893 -0.4108 0.4145 0.051 Uiso 1 1 calc R . . 
C20 C 0.7634(17) 0.1021(11) 0.4334(8) 0.046(3) Uani 1 1 d U . . 
H20A H 0.8596 0.1813 0.4294 0.068 Uiso 1 1 calc R . . 
H20B H 0.8344 0.0265 0.4483 0.068 Uiso 1 1 calc R . . 
H20C H 0.6768 0.1190 0.4817 0.068 Uiso 1 1 calc R . . 
C15 C -0.1062(17) -0.4122(11) 0.3747(8) 0.043(3) Uani 1 1 d U . . 
H15 H -0.1518 -0.4805 0.4125 0.052 Uiso 1 1 calc R . . 
C16 C -0.2392(18) -0.3569(11) 0.3200(8) 0.043(3) Uani 1 1 d U . . 
H16 H -0.3771 -0.3871 0.3193 0.051 Uiso 1 1 calc R . . 
C19 C 0.6412(17) 0.0711(11) 0.3439(7) 0.040(2) Uani 1 1 d U . . 
H19A H 0.5317 0.0001 0.3521 0.048 Uiso 1 1 calc R . . 
H19B H 0.7250 0.0344 0.2994 0.048 Uiso 1 1 calc R . . 
 
 
_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 F3 1.584(7) . ? 
S1 F4 1.588(7) . ? 
S1 F2 1.596(7) . ? 
S1 F5 1.607(6) . ? 
S1 F1 1.609(7) . ? 
S1 C18 1.837(11) . ? 
O2 C10 1.414(12) . ? 
O2 C11 1.444(12) . ? 
O4 C2 1.381(12) . ? 
O4 C1 1.453(12) . ? 
O1 C8 1.207(12) . ? 
C2 C3 1.343(14) . ? 
C2 C7 1.422(14) . ? 
N1 C8 1.395(12) . ? 
N1 C5 1.438(12) . ? 
N1 C9 1.455(13) . ? 
C5 C6 1.359(14) . ? 
C5 C4 1.416(14) . ? 
C12 C13 1.361(15) . ? 
C12 C17 1.404(14) . ? 
C12 C11 1.522(14) . ? 
C17 C16 1.405(15) . ? 
C17 H17 0.9500 . ? 
C6 C7 1.399(13) . ? 
C6 H6 0.9500 . ? 
C9 C18 1.520(14) . ? 
C9 C10 1.594(13) . ? 
C9 H9 1.0000 . ? 
C10 C8 1.523(15) . ? 
C10 H10 1.0000 . ? 
C7 H7 0.9500 . ? 
C11 H11A 0.9900 . ? 
C11 H11B 0.9900 . ? 
C4 C3 1.409(14) . ? 
C4 H4 0.9500 . ? 
C3 H3 0.9500 . ? 
C13 C14 1.404(15) . ? 
C13 H13 0.9500 . ? 
C1 H1A 0.9800 . ? 
C1 H1B 0.9800 . ? 
C1 H1C 0.9800 . ? 
C18 C19 1.548(15) . ? 
C18 H18 1.0000 . ? 
C14 C15 1.389(15) . ? 
C14 H14 0.9500 . ? 
C20 C19 1.482(15) . ? 
C20 H20A 0.9800 . ? 
C20 H20B 0.9800 . ? 
C20 H20C 0.9800 . ? 
C15 C16 1.349(16) . ? 
C15 H15 0.9500 . ? 
C16 H16 0.9500 . ? 
C19 H19A 0.9900 . ? 
C19 H19B 0.9900 . ? 
 
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 
F3 S1 F4 87.7(4) . . ? 
F3 S1 F2 87.7(4) . . ? 
F4 S1 F2 89.7(4) . . ? 
F3 S1 F5 87.4(4) . . ? 
F4 S1 F5 90.0(3) . . ? 
F2 S1 F5 175.2(4) . . ? 
F3 S1 F1 87.4(4) . . ? 
F4 S1 F1 175.1(4) . . ? 
F2 S1 F1 90.5(4) . . ? 
F5 S1 F1 89.5(3) . . ? 
F3 S1 C18 177.2(4) . . ? 
F4 S1 C18 94.9(4) . . ? 
F2 S1 C18 91.1(4) . . ? 
F5 S1 C18 93.8(4) . . ? 
F1 S1 C18 90.0(4) . . ? 
C10 O2 C11 112.8(8) . . ? 
C2 O4 C1 115.5(8) . . ? 
C3 C2 O4 127.1(9) . . ? 
C3 C2 C7 120.9(9) . . ? 
O4 C2 C7 111.9(9) . . ? 
C8 N1 C5 131.0(9) . . ? 
C8 N1 C9 96.7(7) . . ? 
C5 N1 C9 132.1(8) . . ? 
C6 C5 C4 120.9(9) . . ? 
C6 C5 N1 121.9(9) . . ? 
C4 C5 N1 117.2(9) . . ? 
C13 C12 C17 120.2(10) . . ? 
C13 C12 C11 123.7(10) . . ? 
C17 C12 C11 116.1(10) . . ? 
C12 C17 C16 118.9(11) . . ? 
C12 C17 H17 120.6 . . ? 
C16 C17 H17 120.6 . . ? 
C5 C6 C7 120.9(10) . . ? 
C5 C6 H6 119.6 . . ? 
C7 C6 H6 119.6 . . ? 
N1 C9 C18 112.6(9) . . ? 
N1 C9 C10 85.5(7) . . ? 
C18 C9 C10 120.4(8) . . ? 
N1 C9 H9 111.9 . . ? 
C18 C9 H9 111.9 . . ? 
C10 C9 H9 111.9 . . ? 
O2 C10 C8 117.0(9) . . ? 
O2 C10 C9 119.8(8) . . ? 
C8 C10 C9 86.1(7) . . ? 
O2 C10 H10 110.6 . . ? 
C8 C10 H10 110.6 . . ? 
C9 C10 H10 110.6 . . ? 
C6 C7 C2 118.2(10) . . ? 
C6 C7 H7 120.9 . . ? 
C2 C7 H7 120.9 . . ? 
O2 C11 C12 108.3(8) . . ? 
O2 C11 H11A 110.0 . . ? 
C12 C11 H11A 110.0 . . ? 
O2 C11 H11B 110.0 . . ? 
C12 C11 H11B 110.0 . . ? 
H11A C11 H11B 108.4 . . ? 
O1 C8 N1 132.6(10) . . ? 
O1 C8 C10 137.0(9) . . ? 
N1 C8 C10 90.3(8) . . ? 
C3 C4 C5 117.8(10) . . ? 
C3 C4 H4 121.1 . . ? 
C5 C4 H4 121.1 . . ? 
C2 C3 C4 121.3(10) . . ? 
C2 C3 H3 119.4 . . ? 
C4 C3 H3 119.4 . . ? 
C12 C13 C14 120.3(10) . . ? 
C12 C13 H13 119.8 . . ? 
C14 C13 H13 119.8 . . ? 
O4 C1 H1A 109.5 . . ? 
O4 C1 H1B 109.5 . . ? 
H1A C1 H1B 109.5 . . ? 
O4 C1 H1C 109.5 . . ? 
H1A C1 H1C 109.5 . . ? 
H1B C1 H1C 109.5 . . ? 
C9 C18 C19 115.7(8) . . ? 
C9 C18 S1 110.8(7) . . ? 
C19 C18 S1 115.6(7) . . ? 
C9 C18 H18 104.4 . . ? 
C19 C18 H18 104.4 . . ? 
S1 C18 H18 104.4 . . ? 
C15 C14 C13 119.1(11) . . ? 
C15 C14 H14 120.4 . . ? 
C13 C14 H14 120.4 . . ? 
C19 C20 H20A 109.5 . . ? 
C19 C20 H20B 109.5 . . ? 
H20A C20 H20B 109.5 . . ? 
C19 C20 H20C 109.5 . . ? 
H20A C20 H20C 109.5 . . ? 
H20B C20 H20C 109.5 . . ? 
C16 C15 C14 120.9(11) . . ? 
C16 C15 H15 119.5 . . ? 
C14 C15 H15 119.5 . . ? 
C15 C16 C17 120.5(11) . . ? 
C15 C16 H16 119.7 . . ? 
C17 C16 H16 119.7 . . ? 
C20 C19 C18 116.3(9) . . ? 
C20 C19 H19A 108.2 . . ? 
C18 C19 H19A 108.2 . . ? 
C20 C19 H19B 108.2 . . ? 
C18 C19 H19B 108.2 . . ? 
H19A C19 H19B 107.4 . . ? 
#===END
