# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cd214568
_database_code_depnum_ccdc_archive 'CCDC 1048211'
_audit_update_record             
;
2015-02-09 deposited with the CCDC.
2015-07-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H13 F3 N2 O2 S'
_chemical_formula_weight         366.35

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
; 
The symmetry employed for this shelxl refinement is uniquely defined 
by the following loop, which should always be used as a source of 
symmetry information in preference to the above space-group names. 
They are only intended as comments. 
;

loop_
_space_group_symop_operation_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                   17.549(4)
_cell_length_b                   11.355(2)
_cell_length_c                   18.820(4)
_cell_angle_alpha                90
_cell_angle_beta                 111.289(4)
_cell_angle_gamma                90
_cell_volume                     3494.2(12)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3164
_cell_measurement_theta_min      4.502
_cell_measurement_theta_max      49.155

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.393
_exptl_crystal_F_000             1504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.211
_exptl_crystal_size_mid          0.166
_exptl_crystal_size_min          0.123
_exptl_absorpt_coefficient_mu    0.228
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6295
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10399
_diffrn_reflns_av_unetI/netI     0.0372
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.184
_diffrn_reflns_theta_max         25.995
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3430
_reflns_number_gt                2725
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 ? 
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0739P)²+1.3235P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0041(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3430
_refine_ls_number_parameters     255
_refine_ls_number_restraints     36
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0465
_refine_ls_wR_factor_ref         0.1363
_refine_ls_wR_factor_gt          0.1261
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.093
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.18181(3) 1.04451(4) 1.04700(3) 0.0508(2) Uani 1 1 d . . . . .
F1 F 0.4268(5) 0.9287(9) 1.0399(5) 0.0928(16) Uani 0.6 1 d . U P A 1
F2 F 0.4695(6) 1.1016(8) 1.0808(5) 0.123(2) Uani 0.6 1 d . U P A 1
F3 F 0.4197(7) 0.9798(12) 1.1459(9) 0.111(3) Uani 0.5 1 d . U P A 1
F1' F 0.4094(8) 0.9067(16) 1.0538(8) 0.118(3) Uani 0.4 1 d . U P A 2
F2' F 0.4646(8) 1.0754(14) 1.0562(7) 0.119(2) Uani 0.4 1 d . U P A 2
F3' F 0.4391(8) 1.0120(13) 1.1508(9) 0.109(3) Uani 0.5 1 d . U P A 2
N1 N 0.25864(10) 0.99533(14) 1.02164(9) 0.0494(4) Uani 1 1 d . . . . .
N2 N 0.36257(17) 0.7426(2) 0.69227(13) 0.0941(8) Uani 1 1 d . . . . .
O1 O 0.18087(9) 1.16972(13) 1.04745(8) 0.0630(4) Uani 1 1 d . . . . .
O2 O 0.19098(10) 0.98327(15) 1.11544(8) 0.0680(4) Uani 1 1 d . . . . .
C1 C 0.27519(12) 1.05956(17) 0.96080(11) 0.0484(5) Uani 1 1 d . . . . .
H1 H 0.2388 1.1267 0.9399 0.058 Uiso 1 1 calc R U . . .
C2 C 0.32968(12) 1.07339(19) 1.04135(12) 0.0570(5) Uani 1 1 d . . . . .
H2 H 0.3235 1.1482 1.0647 0.068 Uiso 1 1 calc R U . . .
C3 C 0.41135(17) 1.0182(3) 1.07588(16) 0.0816(8) Uani 1 1 d . . . . .
C4 C 0.29378(12) 0.98813(18) 0.90294(11) 0.0487(5) Uani 1 1 d . . . . .
C5 C 0.32120(15) 1.0458(2) 0.85218(13) 0.0618(6) Uani 1 1 d . . . . .
H5 H 0.3272 1.1273 0.8548 0.074 Uiso 1 1 calc R U . . .
C6 C 0.33972(15) 0.9837(2) 0.79772(13) 0.0671(6) Uani 1 1 d . . . . .
H6 H 0.3583 1.0228 0.7637 0.080 Uiso 1 1 calc R U . . .
C7 C 0.33044(13) 0.8633(2) 0.79400(11) 0.0587(5) Uani 1 1 d . . . . .
C8 C 0.30202(15) 0.8048(2) 0.84367(12) 0.0631(6) Uani 1 1 d . . . . .
H8 H 0.2954 0.7235 0.8406 0.076 Uiso 1 1 calc R U . . .
C9 C 0.28363(14) 0.86780(19) 0.89765(12) 0.0586(5) Uani 1 1 d . . . . .
H9 H 0.2641 0.8287 0.9310 0.070 Uiso 1 1 calc R U . . .
C10 C 0.34912(16) 0.7962(2) 0.73729(13) 0.0708(6) Uani 1 1 d . . . . .
C11 C 0.09729(12) 0.99358(18) 0.97113(11) 0.0507(5) Uani 1 1 d . . . . .
C12 C 0.05833(15) 1.0677(2) 0.91123(13) 0.0644(6) Uani 1 1 d . . . . .
H12 H 0.0753 1.1454 0.9121 0.077 Uiso 1 1 calc R U . . .
C13 C -0.00607(15) 1.0255(2) 0.84997(14) 0.0735(7) Uani 1 1 d . . . . .
H13 H -0.0324 1.0757 0.8094 0.088 Uiso 1 1 calc R U . . .
C14 C -0.03255(14) 0.9115(2) 0.84701(13) 0.0668(6) Uani 1 1 d . . . . .
C15 C 0.00601(16) 0.8408(2) 0.90823(16) 0.0808(7) Uani 1 1 d . . . . .
H15 H -0.0121 0.7638 0.9079 0.097 Uiso 1 1 calc R U . . .
C16 C 0.07090(15) 0.8799(2) 0.97034(14) 0.0714(7) Uani 1 1 d . . . . .
H16 H 0.0965 0.8298 1.0112 0.086 Uiso 1 1 calc R U . . .
C17 C -0.10233(18) 0.8678(3) 0.77930(16) 0.0969(9) Uani 1 1 d . . . . .
H17A H -0.1292 0.9334 0.7481 0.145 Uiso 1 1 calc R U . . .
H17B H -0.1405 0.8266 0.7962 0.145 Uiso 1 1 calc R U . . .
H17C H -0.0821 0.8154 0.7502 0.145 Uiso 1 1 calc R U . . .


_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 O2 1.4206(16) . ?
S1 O1 1.4220(16) . ?
S1 N1 1.6807(16) . ?
S1 C11 1.742(2) . ?
F1 C3 1.303(11) . ?
F2 C3 1.371(10) . ?
F3 C3 1.344(17) . ?
F1' C3 1.329(18) . ?
F2' C3 1.297(16) . ?
F3' C3 1.316(16) . ?
N1 C2 1.463(3) . ?
N1 C1 1.473(2) . ?
N2 C10 1.135(3) . ?
C1 C2 1.478(3) . ?
C1 C4 1.486(3) . ?
C1 H1 0.9800 . ?
C2 C3 1.481(3) . ?
C2 H2 0.9800 . ?
C4 C9 1.377(3) . ?
C4 C5 1.381(3) . ?
C5 C6 1.377(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.376(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.379(3) . ?
C7 C10 1.442(3) . ?
C8 C9 1.373(3) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?
C11 C16 1.370(3) . ?
C11 C12 1.374(3) . ?
C12 C13 1.375(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.370(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.365(4) . ?
C14 C17 1.495(3) . ?
C15 C16 1.376(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

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
O2 S1 O1 118.80(10) . . ?
O2 S1 N1 104.85(9) . . ?
O1 S1 N1 110.25(8) . . ?
O2 S1 C11 111.30(10) . . ?
O1 S1 C11 109.18(10) . . ?
N1 S1 C11 100.89(9) . . ?
C2 N1 C1 60.45(13) . . ?
C2 N1 S1 115.10(13) . . ?
C1 N1 S1 117.46(12) . . ?
N1 C1 C2 59.47(13) . . ?
N1 C1 C4 117.20(16) . . ?
C2 C1 C4 125.25(17) . . ?
N1 C1 H1 114.5 . . ?
C2 C1 H1 114.5 . . ?
C4 C1 H1 114.5 . . ?
N1 C2 C1 60.08(12) . . ?
N1 C2 C3 117.0(2) . . ?
C1 C2 C3 124.60(19) . . ?
N1 C2 H2 114.6 . . ?
C1 C2 H2 114.6 . . ?
C3 C2 H2 114.6 . . ?
F2' C3 F3' 107.9(8) . . ?
F2' C3 F1' 109.1(8) . . ?
F3' C3 F1' 104.0(9) . . ?
F1 C3 F3 106.7(7) . . ?
F1 C3 F2 106.4(5) . . ?
F3 C3 F2 110.1(6) . . ?
F2' C3 C2 110.3(7) . . ?
F1 C3 C2 116.9(5) . . ?
F3' C3 C2 114.5(7) . . ?
F1' C3 C2 110.8(6) . . ?
F3 C3 C2 108.1(6) . . ?
F2 C3 C2 108.4(5) . . ?
C9 C4 C5 119.30(18) . . ?
C9 C4 C1 122.52(17) . . ?
C5 C4 C1 118.17(18) . . ?
C6 C5 C4 120.5(2) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C7 C6 C5 119.4(2) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C6 C7 C8 120.58(19) . . ?
C6 C7 C10 120.5(2) . . ?
C8 C7 C10 118.9(2) . . ?
C9 C8 C7 119.4(2) . . ?
C9 C8 H8 120.3 . . ?
C7 C8 H8 120.3 . . ?
C8 C9 C4 120.7(2) . . ?
C8 C9 H9 119.6 . . ?
C4 C9 H9 119.6 . . ?
N2 C10 C7 178.9(3) . . ?
C16 C11 C12 120.2(2) . . ?
C16 C11 S1 120.37(16) . . ?
C12 C11 S1 119.43(17) . . ?
C11 C12 C13 119.2(2) . . ?
C11 C12 H12 120.4 . . ?
C13 C12 H12 120.4 . . ?
C14 C13 C12 121.8(2) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C15 C14 C13 117.7(2) . . ?
C15 C14 C17 121.7(3) . . ?
C13 C14 C17 120.6(2) . . ?
C14 C15 C16 122.1(2) . . ?
C14 C15 H15 119.0 . . ?
C16 C15 H15 119.0 . . ?
C11 C16 C15 119.0(2) . . ?
C11 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

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
O2 S1 N1 C2 -100.01(15) . . . . ?
O1 S1 N1 C2 28.97(16) . . . . ?
C11 S1 N1 C2 144.29(14) . . . . ?
O2 S1 N1 C1 -168.27(14) . . . . ?
O1 S1 N1 C1 -39.29(16) . . . . ?
C11 S1 N1 C1 76.02(15) . . . . ?
S1 N1 C1 C2 104.76(16) . . . . ?
C2 N1 C1 C4 116.8(2) . . . . ?
S1 N1 C1 C4 -138.48(15) . . . . ?
S1 N1 C2 C1 -108.66(15) . . . . ?
C1 N1 C2 C3 -116.2(2) . . . . ?
S1 N1 C2 C3 135.12(18) . . . . ?
C4 C1 C2 N1 -103.5(2) . . . . ?
N1 C1 C2 C3 103.9(3) . . . . ?
C4 C1 C2 C3 0.4(4) . . . . ?
N1 C2 C3 F2' 148.1(5) . . . . ?
C1 C2 C3 F2' 77.2(5) . . . . ?
N1 C2 C3 F1 51.8(5) . . . . ?
C1 C2 C3 F1 -19.0(6) . . . . ?
N1 C2 C3 F3' -90.0(7) . . . . ?
C1 C2 C3 F3' -160.9(7) . . . . ?
N1 C2 C3 F1' 27.2(7) . . . . ?
C1 C2 C3 F1' -43.7(7) . . . . ?
N1 C2 C3 F3 -68.6(6) . . . . ?
C1 C2 C3 F3 -139.4(6) . . . . ?
N1 C2 C3 F2 172.1(4) . . . . ?
C1 C2 C3 F2 101.2(4) . . . . ?
N1 C1 C4 C9 10.3(3) . . . . ?
C2 C1 C4 C9 80.6(3) . . . . ?
N1 C1 C4 C5 -170.63(19) . . . . ?
C2 C1 C4 C5 -100.3(2) . . . . ?
C9 C4 C5 C6 -1.2(3) . . . . ?
C1 C4 C5 C6 179.6(2) . . . . ?
C4 C5 C6 C7 0.2(4) . . . . ?
C5 C6 C7 C8 0.7(3) . . . . ?
C5 C6 C7 C10 179.8(2) . . . . ?
C6 C7 C8 C9 -0.6(3) . . . . ?
C10 C7 C8 C9 -179.7(2) . . . . ?
C7 C8 C9 C4 -0.4(3) . . . . ?
C5 C4 C9 C8 1.3(3) . . . . ?
C1 C4 C9 C8 -179.6(2) . . . . ?
O2 S1 C11 C16 -28.2(2) . . . . ?
O1 S1 C11 C16 -161.26(18) . . . . ?
N1 S1 C11 C16 82.6(2) . . . . ?
O2 S1 C11 C12 153.21(18) . . . . ?
O1 S1 C11 C12 20.1(2) . . . . ?
N1 S1 C11 C12 -95.99(19) . . . . ?
C16 C11 C12 C13 -1.5(4) . . . . ?
S1 C11 C12 C13 177.15(18) . . . . ?
C11 C12 C13 C14 0.0(4) . . . . ?
C12 C13 C14 C15 1.6(4) . . . . ?
C12 C13 C14 C17 -179.5(3) . . . . ?
C13 C14 C15 C16 -1.9(4) . . . . ?
C17 C14 C15 C16 179.2(3) . . . . ?
C12 C11 C16 C15 1.2(4) . . . . ?
S1 C11 C16 C15 -177.4(2) . . . . ?
C14 C15 C16 C11 0.5(4) . . . . ?

_refine_diff_density_max         0.282
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.056

_shelxl_version_number           2013-4

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_cd212733
_database_code_depnum_ccdc_archive 'CCDC 1048213'
_audit_update_record             
;
2015-02-09 deposited with the CCDC.
2015-07-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H6 F3 N O3'
_chemical_formula_weight         233.15

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'

_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, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.8359(6)
_cell_length_b                   6.4223(8)
_cell_length_c                   30.645(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     951.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1964
_cell_measurement_theta_min      5.319
_cell_measurement_theta_max      46.971

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.311
_exptl_crystal_size_mid          0.167
_exptl_crystal_size_min          0.086
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.627
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             472
_exptl_absorpt_coefficient_mu    0.159
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.14145
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5407
_diffrn_reflns_av_R_equivalents  0.0309
_diffrn_reflns_av_sigmaI/netI    0.0287
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.66
_diffrn_reflns_theta_max         25.99
_reflns_number_total             1850
_reflns_number_gt                1583
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_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 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)+(0.0858P)²+0.0954P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.1(15)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1850
_refine_ls_number_parameters     145
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1383
_refine_ls_wR_factor_gt          0.1313
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.067
_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
F1 F -0.0856(6) 0.6497(4) 0.78352(8) 0.1142(9) Uani 1 1 d . . .
F2 F -0.4729(5) 0.6251(4) 0.81285(7) 0.1109(9) Uani 1 1 d . . .
F3 F -0.3973(6) 0.4718(4) 0.75356(6) 0.1222(10) Uani 1 1 d . . .
N1 N 0.5758(4) -0.1646(3) 0.95744(7) 0.0508(5) Uani 1 1 d . . .
O1 O -0.3934(5) 0.2057(4) 0.83343(8) 0.0897(8) Uani 1 1 d U . .
O2 O 0.6855(4) -0.0857(3) 0.98906(7) 0.0680(6) Uani 1 1 d . . .
O3 O 0.6322(5) -0.3388(3) 0.94406(7) 0.0718(6) Uani 1 1 d . . .
C1 C -0.2110(5) 0.3131(5) 0.86231(8) 0.0555(6) Uani 1 1 d . . .
H1 H -0.2886 0.4342 0.8774 0.067 Uiso 1 1 calc R . .
C2 C -0.1864(6) 0.3306(5) 0.81528(8) 0.0587(7) Uani 1 1 d . . .
H2 H -0.0304 0.2567 0.8020 0.070 Uiso 1 1 calc R . .
C3 C -0.2885(7) 0.5154(5) 0.79126(9) 0.0647(7) Uani 1 1 d . . .
C4 C -0.0139(5) 0.1842(4) 0.88777(7) 0.0485(6) Uani 1 1 d . . .
C5 C 0.1052(6) 0.2642(4) 0.92509(7) 0.0498(6) Uani 1 1 d . . .
H5 H 0.0560 0.3967 0.9346 0.060 Uiso 1 1 calc R . .
C6 C 0.2957(5) 0.1510(4) 0.94840(7) 0.0489(6) Uani 1 1 d . . .
H6 H 0.3760 0.2055 0.9735 0.059 Uiso 1 1 calc R . .
C7 C 0.3651(5) -0.0447(4) 0.93384(7) 0.0429(5) Uani 1 1 d . . .
C8 C 0.2442(6) -0.1306(4) 0.89754(8) 0.0559(6) Uani 1 1 d . . .
H8 H 0.2902 -0.2647 0.8887 0.067 Uiso 1 1 calc R . .
C9 C 0.0554(6) -0.0165(4) 0.87457(9) 0.0588(7) Uani 1 1 d . . .
H9 H -0.0276 -0.0734 0.8499 0.071 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
F1 C3 1.328(4) . ?
F2 C3 1.315(3) . ?
F3 C3 1.300(3) . ?
N1 O2 1.215(3) . ?
N1 O3 1.222(3) . ?
N1 C7 1.468(3) . ?
O1 C2 1.398(4) . ?
O1 C1 1.427(3) . ?
C1 C2 1.451(3) . ?
C1 C4 1.484(4) . ?
C1 H1 0.9800 . ?
C2 C3 1.481(4) . ?
C2 H2 0.9800 . ?
C4 C5 1.380(3) . ?
C4 C9 1.392(4) . ?
C5 C6 1.374(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.375(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.372(3) . ?
C8 C9 1.366(4) . ?
C8 H8 0.9300 . ?
C9 H9 0.9300 . ?

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
O2 N1 O3 123.5(2) . . ?
O2 N1 C7 118.5(2) . . ?
O3 N1 C7 118.0(2) . . ?
C2 O1 C1 61.77(17) . . ?
O1 C1 C2 58.13(18) . . ?
O1 C1 C4 117.0(3) . . ?
C2 C1 C4 120.9(2) . . ?
O1 C1 H1 116.1 . . ?
C2 C1 H1 116.1 . . ?
C4 C1 H1 116.1 . . ?
O1 C2 C1 60.10(18) . . ?
O1 C2 C3 114.8(3) . . ?
C1 C2 C3 121.9(3) . . ?
O1 C2 H2 116.0 . . ?
C1 C2 H2 116.0 . . ?
C3 C2 H2 116.0 . . ?
F3 C3 F2 106.7(3) . . ?
F3 C3 F1 106.3(3) . . ?
F2 C3 F1 104.0(3) . . ?
F3 C3 C2 113.8(3) . . ?
F2 C3 C2 113.9(2) . . ?
F1 C3 C2 111.3(3) . . ?
C5 C4 C9 119.0(2) . . ?
C5 C4 C1 119.7(2) . . ?
C9 C4 C1 121.2(2) . . ?
C6 C5 C4 120.9(2) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 118.6(2) . . ?
C5 C6 H6 120.7 . . ?
C7 C6 H6 120.7 . . ?
C8 C7 C6 121.7(2) . . ?
C8 C7 N1 119.0(2) . . ?
C6 C7 N1 119.3(2) . . ?
C9 C8 C7 119.1(2) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C8 C9 C4 120.5(2) . . ?
C8 C9 H9 119.7 . . ?
C4 C9 H9 119.7 . . ?

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
C2 O1 C1 C4 -111.2(3) . . . . ?
C1 O1 C2 C3 -114.0(3) . . . . ?
C4 C1 C2 O1 104.5(3) . . . . ?
O1 C1 C2 C3 102.2(3) . . . . ?
C4 C1 C2 C3 -153.3(3) . . . . ?
O1 C2 C3 F3 -74.0(3) . . . . ?
C1 C2 C3 F3 -142.9(3) . . . . ?
O1 C2 C3 F2 48.7(4) . . . . ?
C1 C2 C3 F2 -20.2(4) . . . . ?
O1 C2 C3 F1 165.9(3) . . . . ?
C1 C2 C3 F1 97.0(4) . . . . ?
O1 C1 C4 C5 -160.0(2) . . . . ?
C2 C1 C4 C5 132.8(3) . . . . ?
O1 C1 C4 C9 20.5(4) . . . . ?
C2 C1 C4 C9 -46.8(4) . . . . ?
C9 C4 C5 C6 1.9(4) . . . . ?
C1 C4 C5 C6 -177.7(2) . . . . ?
C4 C5 C6 C7 -0.2(4) . . . . ?
C5 C6 C7 C8 -1.7(4) . . . . ?
C5 C6 C7 N1 177.7(2) . . . . ?
O2 N1 C7 C8 178.6(2) . . . . ?
O3 N1 C7 C8 -1.1(3) . . . . ?
O2 N1 C7 C6 -0.8(3) . . . . ?
O3 N1 C7 C6 179.4(2) . . . . ?
C6 C7 C8 C9 1.8(4) . . . . ?
N1 C7 C8 C9 -177.6(2) . . . . ?
C7 C8 C9 C4 0.0(4) . . . . ?
C5 C4 C9 C8 -1.8(4) . . . . ?
C1 C4 C9 C8 177.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.046
