# Electronic Supplementary Material (ESI) for New Journal of Chemistry
# This journal is © The Royal Society of Chemistry and The Centre National de la Recherche Scientifique 2012


#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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. 
# 
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material 
#  of the CCDC or of third parties, and may not be copied or further 
#  disseminated in any form, whether machine-readable or not,  
#  except for the purpose of generating routine backup copies 
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and 
#  data retrieval see:
#                         www.ccdc.cam.ac.uk 
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively. 
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data_sad
_database_code_depnum_ccdc_archive 'CCDC 896899'
#TrackingRef '13347_web_deposit_cif_file_0_PierreFrere_1345214574.compound 1 cif.cif'


_audit_creation_date             2012-04-04T16:04:02-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#------------------ CHEMICAL INFORMATION ------------------------------------#

_chemical_formula_moiety         'C24 H6 F10 N4 S1,C H2 Cl2'
_chemical_formula_sum            'C25 H8 Cl2 F10 N4 S'
_chemical_formula_weight         657.31

#------------------ UNIT CELL INFORMATION -----------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
loop_
_symmetry_equiv_pos_as_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                   35.577(5)
_cell_length_b                   6.4458(9)
_cell_length_c                   12.9791(7)
_cell_angle_alpha                90
_cell_angle_beta                 109.18(1)
_cell_angle_gamma                90
_cell_volume                     2811.2(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    10431
_cell_measurement_theta_min      3.53
_cell_measurement_theta_max      27.5

#------------------ CRYSTAL INFORMATION -------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1304
_exptl_absorpt_coefficient_mu    0.395
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.880
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_process_details   
;
'(SADABS (Sheldrick, Bruker, 2008))'
;

#------------------ DATA COLLECTION INFORMATION -----------------------------#

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            30979
_diffrn_reflns_av_R_equivalents  0.0499
_diffrn_reflns_limit_h_min       -46
_diffrn_reflns_limit_h_max       46
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.53
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_full        27.5
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_reflns_number_total             3202
_reflns_number_gt                2334
_reflns_threshold_expression     >2sigma(I)

#------------------ COMPUTER PROGRAMS USED ----------------------------------#

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND 3.2g (Crystal Impact GbR 2005)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#------------------ REFINEMENT INFORMATION ----------------------------------#

_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^)+(0.0439P)^2^+3.6854P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3202
_refine_ls_number_parameters     189
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0802
_refine_ls_R_factor_gt           0.0531
_refine_ls_wR_factor_gt          0.1116
_refine_ls_wR_factor_ref         0.1218
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.239

# SQUEEZE RESULTS
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.250 -0.086 0.351 338.0 76.6
2 0.750 -0.004 0.383 338.0 76.6
_platon_squeeze_details          
;
The unit cell contains disordered methylene chloride molecules which
were not modelled but the corresponding scattering contribution were
taken into account using SQUEEZE/PLATON procedure. The unit cell
contains 2 voids with disordered solvent and each hole of 338 A3
contains about 77 electrons which corresponds to approximately 2
methylene chloride molecules. The solvent composition (four methylene
chloride molecules per cell) was included in the calculation of the
empirical formula, formula weight, density, linear absorption
coefficient and F(000).
;

#------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------#

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 0 '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'
N N 0.0061 0.0033 '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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
_atom_site_disorder_assembly
C1 C 0.01143(6) -0.1132(3) 0.30536(16) 0.0313(4) Uani 1 d . . .
C2 C 0.02056(6) 0.0846(3) 0.34824(15) 0.0291(4) Uani 1 d . . .
C3 C 0.04357(7) 0.1551(3) 0.45613(16) 0.0323(5) Uani 1 d . . .
C4 C 0.05985(6) 0.0412(3) 0.54810(15) 0.0296(4) Uani 1 d . . .
C5 C 0.05496(6) -0.1810(3) 0.55053(15) 0.0309(4) Uani 1 d . . .
C6 C 0.08258(7) 0.1383(3) 0.65179(16) 0.0342(5) Uani 1 d . . .
C7 C 0.11834(6) 0.1007(3) 0.83893(16) 0.0338(5) Uani 1 d . . .
C8 C 0.14500(7) -0.0363(4) 0.91041(18) 0.0405(5) Uani 1 d . . .
C9 C 0.16502(7) 0.0139(4) 1.01754(19) 0.0482(6) Uani 1 d . . .
C10 C 0.15886(7) 0.2038(5) 1.05756(18) 0.0503(6) Uani 1 d . . .
C11 C 0.13328(7) 0.3444(4) 0.98956(19) 0.0453(6) Uani 1 d . . .
C12 C 0.11329(6) 0.2931(3) 0.88200(17) 0.0361(5) Uani 1 d . . .
F1 F 0.15187(4) -0.2222(2) 0.87349(11) 0.0538(4) Uani 1 d . . .
F2 F 0.19039(5) -0.1226(3) 1.08266(13) 0.0748(5) Uani 1 d . . .
F3 F 0.17787(5) 0.2544(3) 1.16167(11) 0.0756(5) Uani 1 d . . .
F4 F 0.12710(5) 0.5301(3) 1.02833(12) 0.0621(4) Uani 1 d . . .
F5 F 0.08720(4) 0.4313(2) 0.82020(11) 0.0483(4) Uani 1 d . . .
N1 N 0.09736(5) 0.0220(3) 0.73489(13) 0.0326(4) Uani 1 d . . .
N2 N 0.05031(6) -0.3558(3) 0.55203(15) 0.0444(5) Uani 1 d . . .
S1 S 0 0.26833(11) 0.25 0.0384(2) Uani 1 d S . .
H1 H 0.0211(6) -0.244(4) 0.3458(17) 0.037(6) Uiso 1 d . . .
H3 H 0.0485(6) 0.301(4) 0.4646(17) 0.033(6) Uiso 1 d . . .
H6 H 0.0865(7) 0.292(4) 0.6530(18) 0.044(6) Uiso 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 0.0353(11) 0.0243(11) 0.0325(10) 0.0019(8) 0.0086(9) 0.0031(8)
C2 0.0392(11) 0.0221(10) 0.0295(10) 0.0011(8) 0.0159(8) 0.0031(8)
C3 0.0457(13) 0.0217(10) 0.0306(10) -0.0028(8) 0.0139(9) -0.0028(9)
C4 0.0371(11) 0.0239(10) 0.0305(10) -0.0014(8) 0.0144(8) -0.0008(8)
C5 0.0361(11) 0.0288(12) 0.0281(10) -0.0015(8) 0.0108(8) 0.0026(9)
C6 0.0429(12) 0.0284(11) 0.0326(11) -0.0006(9) 0.0144(9) -0.0042(9)
C7 0.0326(11) 0.0382(12) 0.0306(10) 0.0002(8) 0.0106(9) -0.0055(9)
C8 0.0373(12) 0.0462(14) 0.0372(11) 0.0022(10) 0.0111(9) -0.0026(10)
C9 0.0352(12) 0.0641(17) 0.0390(12) 0.0123(12) 0.0039(10) -0.0014(12)
C10 0.0413(13) 0.0767(19) 0.0305(11) -0.0044(12) 0.0085(10) -0.0167(13)
C11 0.0467(14) 0.0524(15) 0.0419(12) -0.0146(11) 0.0215(11) -0.0159(12)
C12 0.0349(11) 0.0375(12) 0.0362(11) -0.0023(9) 0.0121(9) -0.0052(9)
F1 0.0596(9) 0.0458(8) 0.0514(8) 0.0066(7) 0.0119(7) 0.0153(7)
F2 0.0634(10) 0.0910(13) 0.0526(9) 0.0183(9) -0.0046(8) 0.0094(9)
F3 0.0707(11) 0.1122(15) 0.0337(7) -0.0113(8) 0.0031(7) -0.0227(11)
F4 0.0732(11) 0.0619(10) 0.0556(9) -0.0269(8) 0.0270(8) -0.0178(8)
F5 0.0586(9) 0.0358(7) 0.0459(7) -0.0055(6) 0.0109(6) 0.0048(6)
N1 0.0351(9) 0.0310(9) 0.0316(8) -0.0005(7) 0.0107(7) 0.0000(7)
N2 0.0591(13) 0.0288(11) 0.0420(11) 0.0005(8) 0.0123(9) 0.0023(9)
S1 0.0662(5) 0.0197(4) 0.0270(3) 0 0.0124(3) 0


#------------------ MOLECULAR GEOMETRY --------------------------------------#

_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 C2 1.387(3) . ?
C1 C1 1.399(4) 2 ?
C1 H1 0.99(2) . ?
C2 C3 1.444(3) . ?
C2 S1 1.7176(19) . ?
C3 C4 1.358(3) . ?
C3 H3 0.96(2) . ?
C4 C5 1.444(3) . ?
C4 C6 1.463(3) . ?
C5 N2 1.140(3) . ?
C6 N1 1.276(3) . ?
C6 H6 1.00(3) . ?
C7 C12 1.396(3) . ?
C7 C8 1.401(3) . ?
C7 N1 1.406(3) . ?
C8 F1 1.342(3) . ?
C8 C9 1.376(3) . ?
C9 F2 1.342(3) . ?
C9 C10 1.375(4) . ?
C10 F3 1.337(3) . ?
C10 C11 1.379(4) . ?
C11 F4 1.344(3) . ?
C11 C12 1.383(3) . ?
C12 F5 1.345(3) . ?
S1 C2 1.7176(19) 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
C2 C1 C1 113.13(11) . 2 ?
C2 C1 H1 125.1(13) . . ?
C1 C1 H1 121.7(13) 2 . ?
C1 C2 C3 131.47(18) . . ?
C1 C2 S1 110.45(14) . . ?
C3 C2 S1 118.08(15) . . ?
C4 C3 C2 128.64(19) . . ?
C4 C3 H3 115.0(13) . . ?
C2 C3 H3 116.4(13) . . ?
C3 C4 C5 122.39(19) . . ?
C3 C4 C6 121.60(19) . . ?
C5 C4 C6 115.99(18) . . ?
N2 C5 C4 178.6(2) . . ?
N1 C6 C4 118.40(19) . . ?
N1 C6 H6 123.5(14) . . ?
C4 C6 H6 118.1(13) . . ?
C12 C7 C8 116.30(19) . . ?
C12 C7 N1 127.4(2) . . ?
C8 C7 N1 116.04(19) . . ?
F1 C8 C9 118.4(2) . . ?
F1 C8 C7 119.30(19) . . ?
C9 C8 C7 122.3(2) . . ?
F2 C9 C10 120.2(2) . . ?
F2 C9 C8 120.0(3) . . ?
C10 C9 C8 119.8(2) . . ?
F3 C10 C9 120.5(3) . . ?
F3 C10 C11 119.7(3) . . ?
C9 C10 C11 119.8(2) . . ?
F4 C11 C10 120.0(2) . . ?
F4 C11 C12 119.9(2) . . ?
C10 C11 C12 120.1(2) . . ?
F5 C12 C11 118.0(2) . . ?
F5 C12 C7 120.26(18) . . ?
C11 C12 C7 121.7(2) . . ?
C6 N1 C7 122.76(19) . . ?
C2 S1 C2 92.84(13) 2 . ?

# start Validation Reply Form
_vrf_CHEMW03_I                   
;
PROBLEM: ALERT: The ratio of given/expected molecular weight as
RESPONSE: The unit cell contains four disordered methylene chloride molecules
which were not modelled but the corresponding scattering contribution were
taken into account using SQUEEZE/PLATON procedure.
The solvent composition (one methylene chloride molecule per formula unit) was
included in the calculation of the empirical formula,molecular weight,density,
linear absorption coefficient and F(000).
.
;
_vrf_PLAT043_I                   
;
PROBLEM: Check Reported Molecular Weight ................ 657.31
RESPONSE: The unit cell contains four disordered methylene chloride molecules
which were not modelled but the corresponding scattering contribution were
taken into account using SQUEEZE/PLATON procedure.
The solvent composition (one methylene chloride molecule per formula unit) was
included in the calculation of the empirical formula and molecular weight.
;
_vrf_PLAT044_I                   
;
PROBLEM: Calculated and Reported Dx Differ .............. ?
RESPONSE: The unit cell contains four disordered methylene chloride molecules
which were not modelled but the corresponding scattering contribution were
taken into account using SQUEEZE/PLATON procedure.
The solvent composition (one methylene chloride molecule per formula unit) was
included in the calculation of the empirical formula and density.
;
_vrf_PLAT051_I                   
;
PROBLEM: Mu(calc) and Mu(CIF) Ratio Differs from 1.0 by . 49.38 Perc.
RESPONSE: The unit cell contains four disordered methylene chloride molecules
which were not modelled but the corresponding scattering contribution were
taken into account using SQUEEZE/PLATON procedure.
The solvent composition (one methylene chloride molecule per formula unit) was
included in the calculation of the empirical formula and linear absorption
coefficient.
;


data_sad2
_database_code_depnum_ccdc_archive 'CCDC 896900'
#TrackingRef '13348_web_deposit_cif_file_1_PierreFrere_1345214574.compound 2cif.cif'


_audit_creation_date             2011-10-04T12:00:02-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#------------------ CHEMICAL INFORMATION ------------------------------------#

_chemical_formula_moiety         'C24 H6 F10 N4 O1'
_chemical_formula_sum            'C24 H6 F10 N4 O'
_chemical_formula_weight         556.33

#------------------ UNIT CELL INFORMATION -----------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
loop_
_symmetry_equiv_pos_as_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                   36.916(9)
_cell_length_b                   6.2980(7)
_cell_length_c                   9.662(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.03(2)
_cell_angle_gamma                90
_cell_volume                     2204.9(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    5616
_cell_measurement_theta_min      4.07
_cell_measurement_theta_max      27.5

#------------------ CRYSTAL INFORMATION -------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.06
_exptl_crystal_density_diffrn    1.676
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1104
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.837
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_process_details   
;
'(SADABS (Sheldrick, Bruker, 2008))'
;

#------------------ DATA COLLECTION INFORMATION -----------------------------#

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_radiation_monochromator  'horizontally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       CCD
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            20708
_diffrn_reflns_av_R_equivalents  0.0723
_diffrn_reflns_limit_h_min       -47
_diffrn_reflns_limit_h_max       45
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.07
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_full        27
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.98
_reflns_number_total             2465
_reflns_number_gt                1420
_reflns_threshold_expression     >2sigma(I)

#------------------ COMPUTER PROGRAMS USED ----------------------------------#

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'DIAMOND 3.2g (Crystal Impact GbR 2005)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'

#------------------ REFINEMENT INFORMATION ----------------------------------#

_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^)+(0.0312P)^2^+3.5517P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2465
_refine_ls_number_parameters     189
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.0581
_refine_ls_wR_factor_ref         0.1339
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_restrained_S_all      1.122
_refine_ls_shift/su_max          0
_refine_diff_density_max         0.171
_refine_diff_density_min         -0.209

#------------------ ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS --------#

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 0 '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 0.006 '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'

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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_group
_atom_site_disorder_assembly
C1 C -0.01402(8) -0.2354(5) 0.6906(3) 0.0494(7) Uani 1 d . . .
C2 C -0.02231(6) -0.0292(4) 0.6558(2) 0.0358(6) Uani 1 d . . .
C3 C -0.04886(7) 0.0752(4) 0.5497(3) 0.0396(6) Uani 1 d . . .
C4 C -0.07011(7) -0.0165(4) 0.4368(3) 0.0377(6) Uani 1 d . . .
C5 C -0.06569(7) -0.2370(5) 0.4044(3) 0.0454(7) Uani 1 d . . .
C6 C -0.09811(7) 0.1001(5) 0.3386(3) 0.0416(7) Uani 1 d . . .
C7 C -0.14557(7) 0.1092(5) 0.1406(3) 0.0439(7) Uani 1 d . . .
C8 C -0.14132(8) 0.3046(5) 0.0804(3) 0.0517(8) Uani 1 d . . .
C9 C -0.16812(10) 0.3886(6) -0.0256(3) 0.0646(9) Uani 1 d . . .
C10 C -0.20030(10) 0.2801(8) -0.0701(3) 0.0764(12) Uani 1 d . . .
C11 C -0.20546(8) 0.0876(7) -0.0141(3) 0.0705(11) Uani 1 d . . .
C12 C -0.17842(8) 0.0033(6) 0.0890(3) 0.0555(8) Uani 1 d . . .
N1 N -0.06066(8) -0.4113(4) 0.3807(3) 0.0668(8) Uani 1 d . . .
N2 N -0.11861(6) 0.0021(4) 0.2382(2) 0.0438(6) Uani 1 d . . .
O1 O 0 0.1004(4) 0.75 0.0390(6) Uani 1 d S . .
F1 F -0.10977(5) 0.4155(3) 0.12063(19) 0.0722(6) Uani 1 d . . .
F2 F -0.16206(7) 0.5765(4) -0.0845(2) 0.0987(8) Uani 1 d . . .
F3 F -0.22649(6) 0.3642(5) -0.1707(2) 0.1190(10) Uani 1 d . . .
F4 F -0.23693(5) -0.0187(5) -0.0579(2) 0.1134(10) Uani 1 d . . .
F5 F -0.18419(5) -0.1886(4) 0.1424(2) 0.0796(7) Uani 1 d . . .
H1 H -0.0253(9) -0.358(6) 0.639(4) 0.083(11) Uiso 1 d . . .
H3 H -0.0520(6) 0.224(5) 0.561(3) 0.040(7) Uiso 1 d . . .
H6 H -0.1005(8) 0.244(5) 0.362(3) 0.064(9) Uiso 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 0.0599(18) 0.0326(16) 0.0469(16) -0.0031(13) -0.0117(13) -0.0033(13)
C2 0.0360(13) 0.0371(14) 0.0311(12) -0.0038(11) -0.0015(10) -0.0020(11)
C3 0.0410(14) 0.0340(15) 0.0399(14) 0.0018(12) -0.0025(11) 0.0006(11)
C4 0.0390(13) 0.0360(15) 0.0355(13) 0.0023(12) 0.0007(11) -0.0022(11)
C5 0.0475(16) 0.0454(18) 0.0374(14) 0.0001(13) -0.0069(12) -0.0053(13)
C6 0.0430(15) 0.0430(17) 0.0350(14) -0.0007(13) -0.0023(12) 0.0009(12)
C7 0.0400(14) 0.0585(19) 0.0302(13) -0.0039(13) -0.0007(11) 0.0016(13)
C8 0.0517(17) 0.064(2) 0.0368(15) 0.0005(14) 0.0027(13) 0.0060(15)
C9 0.080(2) 0.076(2) 0.0366(16) 0.0120(16) 0.0084(16) 0.0255(19)
C10 0.056(2) 0.132(4) 0.0350(17) 0.003(2) -0.0063(15) 0.034(2)
C11 0.0391(17) 0.128(4) 0.0393(17) -0.009(2) -0.0055(14) -0.0003(19)
C12 0.0500(17) 0.079(2) 0.0353(15) -0.0054(16) 0.0016(13) -0.0049(16)
N1 0.085(2) 0.0455(17) 0.0598(17) -0.0087(13) -0.0107(14) -0.0004(14)
N2 0.0404(12) 0.0523(14) 0.0339(11) -0.0019(11) -0.0048(10) -0.0008(10)
O1 0.0416(14) 0.0339(14) 0.0354(13) 0 -0.0084(11) 0
F1 0.0782(13) 0.0692(13) 0.0630(12) 0.0113(10) -0.0018(10) -0.0160(10)
F2 0.134(2) 0.0939(18) 0.0670(13) 0.0325(13) 0.0165(13) 0.0345(15)
F3 0.0868(16) 0.200(3) 0.0576(12) 0.0181(15) -0.0174(11) 0.0657(17)
F4 0.0509(12) 0.201(3) 0.0764(14) -0.0138(17) -0.0174(10) -0.0260(15)
F5 0.0766(13) 0.0963(16) 0.0606(12) -0.0020(11) 0.0000(10) -0.0360(12)


#------------------ MOLECULAR GEOMETRY --------------------------------------#

_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 C2 1.362(4) . ?
C1 C1 1.390(5) 2_556 ?
C1 H1 0.97(4) . ?
C2 O1 1.373(3) . ?
C2 C3 1.435(3) . ?
C3 C4 1.346(3) . ?
C3 H3 0.95(3) . ?
C4 C5 1.440(4) . ?
C4 C6 1.460(3) . ?
C5 N1 1.144(4) . ?
C6 N2 1.270(3) . ?
C6 H6 0.94(3) . ?
C7 C8 1.383(4) . ?
C7 C12 1.390(4) . ?
C7 N2 1.406(3) . ?
C8 F1 1.350(3) . ?
C8 C9 1.386(4) . ?
C9 F2 1.350(4) . ?
C9 C10 1.367(5) . ?
C10 F3 1.342(4) . ?
C10 C11 1.356(6) . ?
C11 F4 1.338(4) . ?
C11 C12 1.374(4) . ?
C12 F5 1.347(4) . ?
O1 C2 1.373(3) 2_556 ?

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
C2 C1 C1 107.48(15) . 2_556 ?
C2 C1 H1 125(2) . . ?
C1 C1 H1 127(2) 2_556 . ?
C1 C2 O1 109.0(2) . . ?
C1 C2 C3 134.7(2) . . ?
O1 C2 C3 116.2(2) . . ?
C4 C3 C2 126.5(3) . . ?
C4 C3 H3 116.7(15) . . ?
C2 C3 H3 116.8(15) . . ?
C3 C4 C5 121.2(2) . . ?
C3 C4 C6 122.8(2) . . ?
C5 C4 C6 116.0(2) . . ?
N1 C5 C4 177.2(3) . . ?
N2 C6 C4 119.7(3) . . ?
N2 C6 H6 125.5(18) . . ?
C4 C6 H6 114.6(18) . . ?
C8 C7 C12 115.9(3) . . ?
C8 C7 N2 125.9(3) . . ?
C12 C7 N2 117.9(3) . . ?
F1 C8 C7 120.0(2) . . ?
F1 C8 C9 118.0(3) . . ?
C7 C8 C9 121.9(3) . . ?
F2 C9 C10 120.7(3) . . ?
F2 C9 C8 119.6(3) . . ?
C10 C9 C8 119.7(3) . . ?
F3 C10 C11 120.4(4) . . ?
F3 C10 C9 119.5(4) . . ?
C11 C10 C9 120.1(3) . . ?
F4 C11 C10 120.1(3) . . ?
F4 C11 C12 120.2(4) . . ?
C10 C11 C12 119.7(3) . . ?
F5 C12 C11 118.5(3) . . ?
F5 C12 C7 118.9(3) . . ?
C11 C12 C7 122.5(3) . . ?
C6 N2 C7 121.4(3) . . ?
C2 O1 C2 107.1(3) . 2_556 ?