_publ_requested_journal          'J. Org. chem.'
_publ_contact_author_name        'Erwann Jeanneau'
_publ_contact_author_address     
;Centre de Diffractom\'etrie Henri Longchambon
Universit\'e Claude Bernard Lyon1
43 boulevard du 11 novembre 1918
F-69622 Villeurbanne cedex
France
;
_publ_contact_author_email       erwann.jeanneau@univ-lyon1.fr

_publ_contact_author_phone       '+33 472 431 859'
_publ_contact_author_fax         '+33 472 431 160'
loop_
_publ_author_name
_publ_author_address
'Saadi, Pierre-Lo\"ic'
;Ecole Normale Sup\'erieure de Lyon
Laboratoire de Chimie
46 all\'ee d'Italie
69364 Lyon cedex 07
France
;
'Guyonnet, Mathieu'
;Ecole Normale Sup\'erieure de Lyon
Laboratoire de Chimie
46 all\'ee d'Italie
69364 Lyon cedex 07
France
;
'Jeanneau, Erwann'
;Centre de Diffractom\'etrie Henri Longchambon
Universit\'e Claude Bernard Lyon1
43 boulevard du 11 novembre 1918
F-69622 Villeurbanne cedex
France
;
'Fleurat-Lessard, Paul'
;Ecole Normale Sup\'erieure de Lyon
Laboratoire de Chimie
46 all\'ee d'Italie
69364 Lyon cedex 07
France
;
'Hasserodt, Jens'
;Ecole Normale Sup\'erieure de Lyon
Laboratoire de Chimie
46 all\'ee d'Italie
69364 Lyon cedex 07
France
;
_audit_creation_date             07-04-24
_audit_creation_method           CRYSTALS_ver_12.84

_cell_length_a                    7.6113(3)
_cell_length_b                    9.9494(3)
_cell_length_c                    16.4236(5)
_cell_angle_alpha                 90
_cell_angle_beta                  102.074(2)
_cell_angle_gamma                 90
_cell_volume                      1216.21(7)
 
_symmetry_cell_setting            'Monoclinic' 
_symmetry_space_group_name_H-M    'P 1 21/n 1 ' 
_symmetry_space_group_name_Hall   '-P 2yn' 
loop_
 _symmetry_equiv_pos_as_xyz
 'x,y,z'
 '-x,-y,-z'
 '-x+1/2,y+1/2,-z+1/2'
 'x+1/2,-y+1/2,z+1/2'

loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source  
 C       0.0033   0.0016   2.3100  20.8439   1.0200  10.2075   1.5886   0.5687
   0.8650  51.6512   0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
 H       0.0000   0.0000   0.4930  10.5109   0.3229  26.1257   0.1402   3.1424
   0.0408  57.7998   0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
 O       0.0106   0.0060   3.0485  13.2771   2.2868   5.7011   1.5463   0.3239
   0.8670  32.9089   0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
 F       0.0171   0.0103   3.5392  10.2825   2.6412   4.2944   1.5170   0.2615
   1.0243  26.1476   0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
 
 
_cell_formula_units_Z                    4

# Given Formula = C9 H9 F9 O3 
# Dc =      1.84 Fooo =    672.00 Mu =      2.20 M =    336.15
# Found Formula = C9 H9 F9 O3 
# Dc =      1.84 FOOO =    672.00 Mu =      2.20 M =    336.15

_chemical_formula_sum             'C9 H9 F9 O3'
_chemical_formula_moiety          'C9 H9 F9 O3'
_chemical_compound_source                ?
_chemical_formula_weight            336.15
 
 
_cell_measurement_reflns_used     2857
_cell_measurement_theta_min        0.679
_cell_measurement_theta_max        27.878
_cell_measurement_temperature          150
 
_exptl_crystal_description        'block' 
_exptl_crystal_colour             'colorless' 
_exptl_crystal_size_min           0.30 
_exptl_crystal_size_mid           0.42 
_exptl_crystal_size_max           0.47 
 
_exptl_crystal_density_diffrn     1.836 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_method     'not measured' 
# Non-dispersive F(000): 
_exptl_crystal_F_000              672 
_exptl_absorpt_coefficient_mu     0.220 
 
# Sheldrick geometric approximatio 0.91 0.94 
_exptl_absorpt_correction_type    none 
_exptl_absorpt_correction_T_min   . 
_exptl_absorpt_correction_T_max   . 
# For a Kappa CCD, set Tmin to 1.0 and 
# Tmax to the ratio of max:min frame scales in scale_all.log 
_diffrn_measurement_device        'Nonius KappaCCD' 
_diffrn_measurement_device_type   'Area' 
_diffrn_radiation_monochromator   'graphite' 
_diffrn_radiation_type            'Mo K\a'
_diffrn_radiation_wavelength           0.71073
_diffrn_measurement_method        '\f & \w scans' 
 
# If a reference occurs more than once, delete the author 
# and date from subsequent references. 
_computing_data_collection        'COLLECT (Nonius, 1997-2001).' 
_computing_cell_refinement        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' 
_computing_data_reduction         'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' 
_computing_structure_solution     'SHELXS 86 (Sheldrick, 1986)' 
_computing_structure_refinement   'CRYSTALS (Betteridge et al., 2003)' 
_computing_publication_material   'CRYSTALS (Betteridge et al., 2003)' 
_computing_molecular_graphics     'CAMERON (Watkin et al., 1996)' 
 
_diffrn_standards_interval_time   . 
_diffrn_standards_interval_count  . 
_diffrn_standards_number          0 
_diffrn_standards_decay_%         ? 
 
_diffrn_ambient_temperature        150
_diffrn_reflns_number             5527 
_reflns_number_total              2784 
_diffrn_reflns_av_R_equivalents   0.029 
# Number of reflections with Friedels Law is 2784 
# Number of reflections without Friedels Law is 0 
# Theoretical number of reflections is about 2899 
 
 
_diffrn_reflns_theta_min          2.408 
_diffrn_reflns_theta_max          27.879 
_diffrn_measured_fraction_theta_max 0.964 
 
_diffrn_reflns_theta_full         27.321 
_diffrn_measured_fraction_theta_full 0.965 
 
 
_diffrn_reflns_limit_h_min        -9 
_diffrn_reflns_limit_h_max        9 
_diffrn_reflns_limit_k_min        -13 
_diffrn_reflns_limit_k_max        13 
_diffrn_reflns_limit_l_min        -21 
_diffrn_reflns_limit_l_max        21 
_reflns_limit_h_min               -9 
_reflns_limit_h_max               9 
_reflns_limit_k_min               0 
_reflns_limit_k_max               13 
_reflns_limit_l_min               0 
_reflns_limit_l_max               21 
 
_oxford_diffrn_Wilson_B_factor    0.00 
_oxford_diffrn_Wilson_scale       0.00 
 
_atom_sites_solution_primary      direct #heavy,direct,difmap,geom
# _atom_sites_solution_secondary  difmap
_atom_sites_solution_hydrogens    geom
 
_refine_diff_density_min          -0.42 
_refine_diff_density_max          0.54 
 
 
# The current dictionary definitions do not cover the 
# situation where the reflections used for refinement were 
# selected by a user-defined sigma threshold 
 
 
# The values actually used during refinement 
_oxford_reflns_threshold_expression_ref     I>2.0\s(I)
_refine_ls_number_reflns          2360 
_refine_ls_number_restraints      0 
_refine_ls_number_parameters      190 
_oxford_refine_ls_R_factor_ref    0.0661 
_refine_ls_wR_factor_ref          0.0719 
_refine_ls_goodness_of_fit_ref    1.0791 
_refine_ls_shift/su_max           0.000405 
 
 
# The values computed from all data 
_oxford_reflns_number_all         2777 
_refine_ls_R_factor_all           0.0733 
_refine_ls_wR_factor_all          0.0757 
 
# The values computed with a 2 sigma cutoff - a la SHELX 
_reflns_threshold_expression      I>2.0\s(I)
_reflns_number_gt                 2360 
_refine_ls_R_factor_gt            0.0661 
_refine_ls_wR_factor_gt           0.0719 
 
# choose from: rm (reference molecule of known chirality), 
# ad (anomolous dispersion - Flack), rmad (rm and ad), 
# syn (from synthesis), unk (unknown) or . (not applicable). 
_chemical_absolute_configuration  '.' 
 
 
_refine_ls_structure_factor_coef  F 
_refine_ls_matrix_type            full
_refine_ls_hydrogen_treatment     constr         # none, undef, noref, refall,
                                                 # refxyz, refU, constr or mixed
_refine_ls_weighting_scheme       calc 
_refine_ls_weighting_details 
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] 
 where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ 
 A~i~ are: 
 1.27 0.910 0.801 
;
# Insert your own references if required - in alphabetical order 
_publ_section_references 
; 
Betteridge, P.W., Carruthers, J.R., Cooper, R.I., 
Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. 
 
Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. 
 
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, 
edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. 
New York: Academic Press. 
 
Prince, E. 
Mathematical Techniques in Crystallography 
and Materials Science 
Springer-Verlag, New York, 1982. 
 
Sheldrick, G.M. (1986). SHELXS86. Program for the solution of 
crystal structures. Univ. of G\"ottingen, Federal Republic of Germany. 
 
Watkin D.J. (1994). 
Acta Cryst, A50, 411-437. 
 
Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical 
Crystallography Laboratory, Oxford, UK. 
; 

# Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3

# Replace last . with number of unfound hydrogen atomsattached to an atom.

# ..._refinement_flags_... 
# . no refinement constraints           S special position constraint on site
# G rigid group refinement of site      R riding atom
# D distance or angle restraint on site T thermal displacement constraints
# U Uiso or Uij restraint (rigid bond)  P partial occupancy constraint


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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_oxford_atom_site_special_shape
_atom_site_attached_hydrogens
C1 C 0.3037(2) 0.38342(16) 0.58884(10) 0.0343 1.0000 Uani . . . . . . . 
C2 C 0.33586(19) 0.51312(14) 0.64039(9) 0.0268 1.0000 Uani . . . . . . . 
C3 C 0.2733(2) 0.63405(15) 0.58524(9) 0.0300 1.0000 Uani . . . . . . . 
C4 C 0.3266(2) 0.76270(15) 0.63454(9) 0.0293 1.0000 Uani . . . . . . . 
C5 C 0.2834(3) 0.88470(18) 0.57682(12) 0.0467 1.0000 Uani . . . . . . . 
C6 C 0.52239(19) 0.76703(14) 0.66958(10) 0.0296 1.0000 Uani . . . . . . . 
C7 C 0.6134(2) 0.64098(17) 0.70791(11) 0.0354 1.0000 Uani . . . . . . . 
C8 C 0.6253(2) 0.6427(2) 0.80308(11) 0.0410 1.0000 Uani . . . . . . . 
C9 C 0.8032(3) 0.6360(4) 0.69277(17) 0.0777 1.0000 Uani . . . . . . . 
F7 F 0.46899(14) 0.64725(12) 0.82539(6) 0.0422 1.0000 Uani . . . . . . . 
F9 F 0.7080(2) 0.53265(18) 0.83844(9) 0.0755 1.0000 Uani . . . . . . . 
F8 F 0.7189(2) 0.74873(17) 0.83764(9) 0.0715 1.0000 Uani . . . . . . . 
O1 O 0.52596(16) 0.51589(12) 0.67401(8) 0.0391 1.0000 Uani . . . . . . . 
O2 O 0.23299(15) 0.50281(12) 0.70153(7) 0.0338 1.0000 Uani . . . . . . . 
O3 O 0.22310(16) 0.77695(13) 0.69591(7) 0.0376 1.0000 Uani . . . . . . . 
F5 F 0.3252(2) 0.99930(11) 0.61885(8) 0.0590 1.0000 Uani . . . . . . . 
F4 F 0.1093(2) 0.88886(14) 0.54252(10) 0.0696 1.0000 Uani . . . . . . . 
F6 F 0.3728(3) 0.88183(13) 0.51551(9) 0.0698 1.0000 Uani . . . . . . . 
F1 F 0.35605(15) 0.27551(9) 0.63586(7) 0.0419 1.0000 Uani . . . . . . . 
F2 F 0.13137(16) 0.36809(11) 0.55409(7) 0.0493 1.0000 Uani . . . . . . . 
F3 F 0.39520(19) 0.38370(11) 0.52751(7) 0.0518 1.0000 Uani . . . . . . . 
H31 H 0.1450 0.6257 0.5678 0.0356 1.0000 Uiso R . . . . . . 
H32 H 0.3303 0.6289 0.5385 0.0352 1.0000 Uiso R . . . . . . 
H61 H 0.5378 0.8336 0.7078 0.0384 1.0000 Uiso R . . . . . . 
H62 H 0.5761 0.7900 0.6235 0.0388 1.0000 Uiso R . . . . . . 
H91 H 0.8598 0.5550 0.7159 0.1167 1.0000 Uiso R . . . . . . 
H92 H 0.8728 0.7096 0.7193 0.1151 1.0000 Uiso R . . . . . . 
H93 H 0.8006 0.6355 0.6330 0.1152 1.0000 Uiso R . . . . . . 
H3 H 0.2320 0.7090 0.7234 0.0597 1.0000 Uiso R . . . . . . 
H2 H 0.2728 0.4531 0.7375 0.0540 1.0000 Uiso R . . . . . . 
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 0.0432(9) 0.0267(7) 0.0336(7) -0.0032(5) 0.0091(6) -0.0049(6) 
C2 0.0286(7) 0.0252(7) 0.0265(6) -0.0009(5) 0.0054(5) -0.0020(5) 
C3 0.0336(7) 0.0280(7) 0.0270(6) -0.0003(5) 0.0029(5) 0.0010(5) 
C4 0.0341(8) 0.0244(7) 0.0301(7) -0.0004(5) 0.0083(6) 0.0009(5) 
C5 0.0735(13) 0.0273(8) 0.0410(9) 0.0046(6) 0.0156(9) 0.0071(8) 
C6 0.0291(7) 0.0219(6) 0.0372(7) -0.0007(5) 0.0056(6) -0.0055(5) 
C7 0.0259(7) 0.0407(9) 0.0389(8) -0.0003(6) 0.0051(6) -0.0006(6) 
C8 0.0329(8) 0.0485(10) 0.0373(8) -0.0019(7) -0.0026(6) 0.0033(7) 
C9 0.0252(9) 0.147(3) 0.0622(14) -0.0057(15) 0.0117(9) 0.0004(12) 
F7 0.0420(6) 0.0526(7) 0.0315(5) -0.0038(4) 0.0065(4) -0.0012(4) 
F9 0.0850(10) 0.0874(11) 0.0485(7) 0.0105(7) 0.0011(7) 0.0472(9) 
F8 0.0695(9) 0.0891(11) 0.0488(7) -0.0136(7) -0.0038(6) -0.0416(8) 
O1 0.0380(7) 0.0319(6) 0.0456(7) -0.0034(5) 0.0049(5) 0.0028(4) 
O2 0.0338(6) 0.0392(6) 0.0301(5) 0.0008(4) 0.0110(4) -0.0055(4) 
O3 0.0382(6) 0.0414(7) 0.0353(6) 0.0021(5) 0.0126(5) 0.0080(5) 
F5 0.0976(11) 0.0238(5) 0.0612(7) 0.0016(5) 0.0294(7) 0.0021(5) 
F4 0.0844(10) 0.0503(7) 0.0626(8) 0.0152(6) -0.0110(7) 0.0232(7) 
F6 0.1296(14) 0.0392(7) 0.0526(7) 0.0116(5) 0.0462(8) 0.0035(7) 
F1 0.0545(6) 0.0235(5) 0.0490(6) 0.0006(4) 0.0138(5) 0.0005(4) 
F2 0.0503(7) 0.0424(6) 0.0484(6) -0.0093(4) -0.0055(5) -0.0128(5) 
F3 0.0792(9) 0.0381(6) 0.0469(6) -0.0124(4) 0.0332(6) -0.0094(5) 

_refine_ls_extinction_method 
    'None'
_oxford_refine_ls_scale 1.162(4) 
loop_
 _geom_bond_atom_site_label_1
 _geom_bond_site_symmetry_1
 _geom_bond_atom_site_label_2
 _geom_bond_site_symmetry_2
 _geom_bond_distance
 _geom_bond_publ_flag
C1 . C2 . 1.535(2)    yes
C1 . F1 . 1.3338(19)    yes
C1 . F2 . 1.325(2)    yes
C1 . F3 . 1.339(2)    yes
C2 . C3 . 1.521(2)    yes
C2 . O1 . 1.4370(19)    yes
C2 . O2 . 1.4003(18)    yes
C3 . C4 . 1.523(2)    yes
C3 . H31 . 0.962    no
C3 . H32 . 0.959    no
C4 . C5 . 1.533(2)    yes
C4 . C6 . 1.482(2)    yes
C4 . O3 . 1.4101(19)    yes
C5 . F5 . 1.336(2)    yes
C5 . F4 . 1.327(3)    yes
C5 . F6 . 1.328(2)    yes
C6 . C7 . 1.505(2)    yes
C6 . H61 . 0.904    no
C6 . H62 . 0.960    no
C7 . C8 . 1.547(3)    yes
C7 . C9 . 1.517(3)    yes
C7 . O1 . 1.465(2)    yes
C8 . F7 . 1.317(2)    yes
C8 . F9 . 1.334(2)    yes
C8 . F8 . 1.332(2)    yes
C9 . H91 . 0.954    no
C9 . H92 . 0.954    no
C9 . H93 . 0.977    no
O2 . H2 . 0.781    no
O3 . H3 . 0.808    no
loop_
 _geom_angle_atom_site_label_1
 _geom_angle_site_symmetry_1
 _geom_angle_atom_site_label_2
 _geom_angle_site_symmetry_2
 _geom_angle_atom_site_label_3
 _geom_angle_site_symmetry_3
 _geom_angle
 _geom_angle_publ_flag
C2 . C1 . F1 . 111.32(13)    yes
C2 . C1 . F2 . 111.34(14)    yes
F1 . C1 . F2 . 107.81(13)    yes
C2 . C1 . F3 . 111.40(13)    yes
F1 . C1 . F3 . 107.31(14)    yes
F2 . C1 . F3 . 107.46(15)    yes
C1 . C2 . C3 . 110.04(12)    yes
C1 . C2 . O1 . 105.07(12)    yes
C3 . C2 . O1 . 112.21(12)    yes
C1 . C2 . O2 . 106.58(12)    yes
C3 . C2 . O2 . 109.43(12)    yes
O1 . C2 . O2 . 113.26(12)    yes
C2 . C3 . C4 . 109.45(12)    yes
C2 . C3 . H31 . 106.3    no
C4 . C3 . H31 . 111.8    no
C2 . C3 . H32 . 107.3    no
C4 . C3 . H32 . 110.9    no
H31 . C3 . H32 . 110.9    no
C3 . C4 . C5 . 109.75(13)    yes
C3 . C4 . C6 . 111.40(12)    yes
C5 . C4 . C6 . 106.58(14)    yes
C3 . C4 . O3 . 109.76(13)    yes
C5 . C4 . O3 . 106.43(13)    yes
C6 . C4 . O3 . 112.71(13)    yes
C4 . C5 . F5 . 111.05(15)    yes
C4 . C5 . F4 . 110.67(17)    yes
F5 . C5 . F4 . 107.55(17)    yes
C4 . C5 . F6 . 111.97(16)    yes
F5 . C5 . F6 . 107.78(17)    yes
F4 . C5 . F6 . 107.63(18)    yes
C4 . C6 . C7 . 118.40(12)    yes
C4 . C6 . H61 . 105.4    no
C7 . C6 . H61 . 109.8    no
C4 . C6 . H62 . 105.1    no
C7 . C6 . H62 . 107.1    no
H61 . C6 . H62 . 111.0    no
C6 . C7 . C8 . 109.74(14)    yes
C6 . C7 . C9 . 109.23(18)    yes
C8 . C7 . C9 . 108.03(16)    yes
C6 . C7 . O1 . 114.59(12)    yes
C8 . C7 . O1 . 108.62(14)    yes
C9 . C7 . O1 . 106.40(18)    yes
C7 . C8 . F7 . 114.61(13)    yes
C7 . C8 . F9 . 110.69(16)    yes
F7 . C8 . F9 . 106.17(17)    yes
C7 . C8 . F8 . 110.65(16)    yes
F7 . C8 . F8 . 106.74(16)    yes
F9 . C8 . F8 . 107.64(16)    yes
C7 . C9 . H91 . 109.2    no
C7 . C9 . H92 . 110.9    no
H91 . C9 . H92 . 107.8    no
C7 . C9 . H93 . 110.2    no
H91 . C9 . H93 . 107.9    no
H92 . C9 . H93 . 110.8    no
C7 . O1 . C2 . 120.21(11)    yes
C2 . O2 . H2 . 113.6    no
C4 . O3 . H3 . 108.8    no
loop_
 _geom_hbond_atom_site_label_D
 _geom_hbond_site_symmetry_D
 _geom_hbond_atom_site_label_H
 _geom_hbond_site_symmetry_H
 _geom_hbond_atom_site_label_A
 _geom_hbond_site_symmetry_A
 _geom_hbond_angle_DHA
 _geom_hbond_distance_DH
 _geom_hbond_distance_HA
 _geom_hbond_distance_DA
 _geom_hbond_publ_flag
O3 . H3 . O2 . 137 0.81 2.08 2.730(3)    yes
O2 . H2 . O3 3_546 154 0.78 2.06 2.786(3)    yes
