# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               Org.Biomol.Chem.
_journal_coden_cambridge         0177
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_author_name                G.Haufe
_publ_contact_author_name        ' G.Haufe'
_publ_contact_author_email       haufe@uni-muenster.de

data_haf5353
_database_code_depnum_ccdc_archive 'CCDC 887922'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H10 F5 N O4'
_chemical_formula_weight         303.19

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           triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   6.4262(3)
_cell_length_b                   9.9510(3)
_cell_length_c                   10.4639(4)
_cell_angle_alpha                73.787(2)
_cell_angle_beta                 86.704(2)
_cell_angle_gamma                75.894(2)
_cell_volume                     623.11(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    223(2)
_cell_measurement_reflns_used    1431
_cell_measurement_theta_min      4.08
_cell_measurement_theta_max      27.88

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.616
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             308
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9430
_exptl_absorpt_correction_T_max  0.9750
_exptl_absorpt_process_details   
'Denzo (Otwinowski, Borek, Majewski & Minor, 2003)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      223(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode Nonius FR591'
_diffrn_radiation_monochromator  'Montel mirror'
_diffrn_measurement_device_type  'Nonius KappaCCD APEXII'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5389
_diffrn_reflns_av_R_equivalents  0.052
_diffrn_reflns_av_sigmaI/netI    0.0344
_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       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.30
_diffrn_reflns_theta_max         26.30
_reflns_number_total             2442
_reflns_number_gt                2073
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius B.V., 1998)'
_computing_cell_refinement       'Collect (Nonius B.V., 1998)'
_computing_data_reduction        'Denzo-SMN (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (BrukerAXS, 2000)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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.

The hydrogen H21 of the N21 atom was refined freely.
;

_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^)+(0.0490P)^2^+0.8369P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   'at N from difmap, others geom'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2442
_refine_ls_number_parameters     187
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0763
_refine_ls_R_factor_gt           0.0646
_refine_ls_wR_factor_ref         0.1566
_refine_ls_wR_factor_gt          0.1438
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_restrained_S_all      1.066
_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
O1 O 0.3500(3) 0.4651(2) 0.38239(19) 0.0417(5) Uani 1 1 d . . .
C1 C 0.3105(4) 0.3475(3) 0.4166(3) 0.0334(6) Uani 1 1 d . . .
C2 C 0.4153(4) 0.2329(3) 0.5329(2) 0.0306(5) Uani 1 1 d . . .
C3 C 0.3486(4) 0.1115(3) 0.5854(3) 0.0319(5) Uani 1 1 d . . .
H3 H 0.2441 0.0941 0.5368 0.038 Uiso 1 1 calc R . .
C4 C 0.4212(4) 0.0060(3) 0.7078(3) 0.0342(6) Uani 1 1 d . . .
H4 H 0.5357 0.0167 0.7530 0.041 Uiso 1 1 calc R . .
C5 C 0.3371(4) -0.1069(3) 0.7622(3) 0.0342(6) Uani 1 1 d . . .
O5 O 0.1753(4) -0.1443(2) 0.7166(2) 0.0494(6) Uani 1 1 d . . .
H5 H 0.0957 -0.0716 0.6678 0.074 Uiso 1 1 calc R . .
C6 C 0.4211(4) -0.2146(3) 0.8912(3) 0.0379(6) Uani 1 1 d . . .
F1 F 0.4432(3) -0.35041(17) 0.88240(19) 0.0540(5) Uani 1 1 d . . .
F2 F 0.6158(3) -0.2038(2) 0.92227(19) 0.0568(5) Uani 1 1 d . . .
C7 C 0.2795(6) -0.2023(4) 1.0119(3) 0.0503(8) Uani 1 1 d . . .
F3 F 0.2575(4) -0.0739(3) 1.0312(2) 0.0811(7) Uani 1 1 d . . .
F4 F 0.0878(3) -0.2199(3) 0.9964(2) 0.0798(7) Uani 1 1 d . . .
F5 F 0.3667(4) -0.3004(3) 1.12076(19) 0.0749(7) Uani 1 1 d . . .
O11 O 0.1690(3) 0.3089(2) 0.3561(2) 0.0437(5) Uani 1 1 d . . .
C12 C 0.0585(5) 0.4166(3) 0.2393(3) 0.0448(7) Uani 1 1 d . . .
H12A H 0.0122 0.3684 0.1801 0.054 Uiso 1 1 calc R . .
H12B H 0.1568 0.4736 0.1902 0.054 Uiso 1 1 calc R . .
C13 C -0.1309(6) 0.5128(4) 0.2819(4) 0.0654(10) Uani 1 1 d . . .
H13A H -0.2276 0.4560 0.3307 0.098 Uiso 1 1 calc R . .
H13B H -0.2047 0.5831 0.2041 0.098 Uiso 1 1 calc R . .
H13C H -0.0841 0.5623 0.3386 0.098 Uiso 1 1 calc R . .
N21 N 0.5839(4) 0.2685(2) 0.5874(2) 0.0337(5) Uani 1 1 d . . .
H21 H 0.573(5) 0.349(4) 0.592(3) 0.037(8) Uiso 1 1 d . . .
C22 C 0.7834(4) 0.1873(3) 0.6119(3) 0.0358(6) Uani 1 1 d . . .
H22 H 0.8843 0.2274 0.6405 0.043 Uiso 1 1 calc R . .
O23 O 0.8458(3) 0.0653(2) 0.6002(2) 0.0410(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
O1 0.0523(12) 0.0322(10) 0.0444(11) -0.0064(8) -0.0045(9) -0.0205(9)
C1 0.0352(13) 0.0327(13) 0.0370(13) -0.0127(11) 0.0032(11) -0.0140(11)
C2 0.0295(12) 0.0317(13) 0.0349(13) -0.0135(11) 0.0026(10) -0.0106(10)
C3 0.0277(12) 0.0344(13) 0.0375(13) -0.0131(11) 0.0028(10) -0.0111(10)
C4 0.0328(13) 0.0363(13) 0.0371(14) -0.0120(11) 0.0024(11) -0.0135(11)
C5 0.0317(13) 0.0346(13) 0.0374(14) -0.0109(11) 0.0000(10) -0.0086(10)
O5 0.0518(13) 0.0402(11) 0.0553(13) 0.0041(9) -0.0173(10) -0.0248(10)
C6 0.0341(14) 0.0371(14) 0.0421(15) -0.0099(12) -0.0015(11) -0.0082(11)
F1 0.0682(12) 0.0309(8) 0.0564(11) -0.0069(8) -0.0044(9) -0.0039(8)
F2 0.0403(10) 0.0655(12) 0.0567(11) 0.0011(9) -0.0131(8) -0.0155(8)
C7 0.0582(19) 0.0528(18) 0.0413(16) -0.0124(14) 0.0031(14) -0.0168(15)
F3 0.1105(19) 0.0709(14) 0.0686(14) -0.0391(12) 0.0143(13) -0.0142(13)
F4 0.0538(13) 0.122(2) 0.0681(14) -0.0245(14) 0.0183(10) -0.0348(13)
F5 0.0940(17) 0.0826(15) 0.0385(10) 0.0002(10) 0.0004(10) -0.0222(13)
O11 0.0473(11) 0.0336(10) 0.0509(12) -0.0027(9) -0.0163(9) -0.0173(9)
C12 0.0455(16) 0.0431(16) 0.0468(16) -0.0086(13) -0.0046(13) -0.0151(13)
C13 0.0484(19) 0.073(2) 0.070(2) -0.019(2) 0.0020(17) -0.0084(17)
N21 0.0367(12) 0.0288(11) 0.0410(12) -0.0135(10) 0.0001(9) -0.0131(9)
C22 0.0338(14) 0.0415(15) 0.0372(14) -0.0128(12) 0.0017(11) -0.0165(11)
O23 0.0331(10) 0.0405(11) 0.0526(12) -0.0168(9) 0.0006(8) -0.0096(8)

_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
O1 C1 1.210(3) . ?
C1 O11 1.322(3) . ?
C1 C2 1.476(4) . ?
C2 C3 1.342(3) . ?
C2 N21 1.413(3) . ?
C3 C4 1.428(4) . ?
C3 H3 0.9400 . ?
C4 C5 1.335(4) . ?
C4 H4 0.9400 . ?
C5 O5 1.339(3) . ?
C5 C6 1.502(4) . ?
O5 H5 0.8300 . ?
C6 F2 1.347(3) . ?
C6 F1 1.353(3) . ?
C6 C7 1.529(4) . ?
C7 F4 1.312(4) . ?
C7 F3 1.322(4) . ?
C7 F5 1.323(4) . ?
O11 C12 1.464(3) . ?
C12 C13 1.485(5) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 H13C 0.9700 . ?
N21 C22 1.334(3) . ?
N21 H21 0.80(3) . ?
C22 O23 1.221(3) . ?
C22 H22 0.9400 . ?

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
O1 C1 O11 124.1(2) . . ?
O1 C1 C2 122.6(2) . . ?
O11 C1 C2 113.3(2) . . ?
C3 C2 N21 123.8(2) . . ?
C3 C2 C1 123.2(2) . . ?
N21 C2 C1 113.0(2) . . ?
C2 C3 C4 126.3(2) . . ?
C2 C3 H3 116.9 . . ?
C4 C3 H3 116.9 . . ?
C5 C4 C3 124.3(2) . . ?
C5 C4 H4 117.9 . . ?
C3 C4 H4 117.9 . . ?
C4 C5 O5 128.5(2) . . ?
C4 C5 C6 121.8(2) . . ?
O5 C5 C6 109.7(2) . . ?
C5 O5 H5 109.5 . . ?
F2 C6 F1 107.0(2) . . ?
F2 C6 C5 111.4(2) . . ?
F1 C6 C5 110.5(2) . . ?
F2 C6 C7 106.3(2) . . ?
F1 C6 C7 106.1(2) . . ?
C5 C6 C7 115.1(2) . . ?
F4 C7 F3 108.2(3) . . ?
F4 C7 F5 107.8(3) . . ?
F3 C7 F5 108.0(3) . . ?
F4 C7 C6 111.9(3) . . ?
F3 C7 C6 110.0(3) . . ?
F5 C7 C6 110.8(3) . . ?
C1 O11 C12 116.6(2) . . ?
O11 C12 C13 109.8(3) . . ?
O11 C12 H12A 109.7 . . ?
C13 C12 H12A 109.7 . . ?
O11 C12 H12B 109.7 . . ?
C13 C12 H12B 109.7 . . ?
H12A C12 H12B 108.2 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C22 N21 C2 125.7(2) . . ?
C22 N21 H21 113(2) . . ?
C2 N21 H21 120(2) . . ?
O23 C22 N21 125.4(2) . . ?
O23 C22 H22 117.3 . . ?
N21 C22 H22 117.3 . . ?

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
O1 C1 C2 C3 168.5(3) . . . . ?
O11 C1 C2 C3 -10.6(4) . . . . ?
O1 C1 C2 N21 -8.0(4) . . . . ?
O11 C1 C2 N21 172.9(2) . . . . ?
N21 C2 C3 C4 5.6(4) . . . . ?
C1 C2 C3 C4 -170.5(2) . . . . ?
C2 C3 C4 C5 173.8(3) . . . . ?
C3 C4 C5 O5 0.1(5) . . . . ?
C3 C4 C5 C6 179.8(2) . . . . ?
C4 C5 C6 F2 -16.1(4) . . . . ?
O5 C5 C6 F2 163.6(2) . . . . ?
C4 C5 C6 F1 -135.0(3) . . . . ?
O5 C5 C6 F1 44.8(3) . . . . ?
C4 C5 C6 C7 104.9(3) . . . . ?
O5 C5 C6 C7 -75.3(3) . . . . ?
F2 C6 C7 F4 -176.2(3) . . . . ?
F1 C6 C7 F4 -62.5(3) . . . . ?
C5 C6 C7 F4 60.0(4) . . . . ?
F2 C6 C7 F3 63.5(3) . . . . ?
F1 C6 C7 F3 177.2(2) . . . . ?
C5 C6 C7 F3 -60.3(3) . . . . ?
F2 C6 C7 F5 -55.8(3) . . . . ?
F1 C6 C7 F5 57.9(3) . . . . ?
C5 C6 C7 F5 -179.6(2) . . . . ?
O1 C1 O11 C12 1.1(4) . . . . ?
C2 C1 O11 C12 -179.8(2) . . . . ?
C1 O11 C12 C13 -85.3(3) . . . . ?
C3 C2 N21 C22 55.8(4) . . . . ?
C1 C2 N21 C22 -127.8(3) . . . . ?
C2 N21 C22 O23 -5.9(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.967
_diffrn_reflns_theta_full        26.30
_diffrn_measured_fraction_theta_full 0.967
_refine_diff_density_max         0.371
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.058