# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Angelo Gavezzotti'
_publ_contact_author_email       ANGELO.GAVEZZOTTI@UNIMI.IT

_publ_section_title              
;
Competition between hydrogen bonding and
arene-perfluoroarene stacking. X-ray diffraction and molecular
simulation on 5,6,7,8-tetrafluoro-2-naphthoic acid and
5,6,7,8-tetrafluoro-2-naphthamide crystals
;
loop_
_publ_author_name
'Angelo Gavezzotti'
'Sergio Bacchi'
'Franco Cozzi'
'Giuseppe Filippini'
'Tullio Pilati'

# Attachment 'msgave_cif.doc'

data_cz7_93k
_database_code_depnum_ccdc_archive 'CCDC 697372'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H4 F4 O2'
_chemical_formula_sum            'C11 H4 F4 O2'
_chemical_formula_weight         244.14

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   4.943(2)
_cell_length_b                   5.902(2)
_cell_length_c                   30.706(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.880(10)
_cell_angle_gamma                90.00
_cell_volume                     895.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    886
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      25.89

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.810
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    0.179
_exptl_absorpt_correction_type   none

_exptl_special_details           
;
OXFORD low temperature device.
;

_diffrn_ambient_temperature      93(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  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_standards_decay_%        0.00
_diffrn_reflns_number            5114
_diffrn_reflns_av_R_equivalents  0.0751
_diffrn_reflns_av_sigmaI/netI    0.0875
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.65
_diffrn_reflns_theta_max         28.08
_reflns_number_total             2028
_reflns_number_gt                1166
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    
;
M.C. Burla, M. Camalli, B. Carrozzini, G.L. Cascarano, C. Giacovazzo,
G. Polidori, R. Spagna (2003).
SIR2002: the program. J. Appl. Cryst. 36,1103
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEP-III (Burnett and Johnson, 1996), Mercury 1.4, CCDC'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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     
'w=1/[σ²(Fo²)+(0.0315P)²] 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         2028
_refine_ls_number_parameters     170
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0794
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.0940
_refine_ls_wR_factor_gt          0.0836
_refine_ls_goodness_of_fit_ref   0.820
_refine_ls_restrained_S_all      0.820
_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
C1 C 0.0708(4) 0.4807(4) 0.10550(7) 0.0200(5) Uani 1 1 d . . .
C2 C 0.0042(4) 0.3477(3) 0.07024(7) 0.0189(5) Uani 1 1 d . . .
C3 C 0.1419(4) 0.1421(4) 0.06306(7) 0.0231(5) Uani 1 1 d . . .
C4 C 0.3400(4) 0.0716(4) 0.09113(7) 0.0234(5) Uani 1 1 d . . .
C5 C 0.4127(4) 0.2043(3) 0.12775(7) 0.0203(5) Uani 1 1 d . . .
C6 C 0.6180(4) 0.1387(3) 0.15744(7) 0.0234(5) Uani 1 1 d . . .
C7 C 0.6903(4) 0.2708(4) 0.19189(7) 0.0252(5) Uani 1 1 d . . .
C8 C 0.5555(4) 0.4749(4) 0.19913(7) 0.0255(5) Uani 1 1 d . . .
C9 C 0.3543(4) 0.5430(4) 0.17139(7) 0.0228(5) Uani 1 1 d . . .
C10 C 0.2768(4) 0.4123(3) 0.13513(7) 0.0196(5) Uani 1 1 d . . .
C11 C -0.2105(4) 0.4185(3) 0.03898(7) 0.0207(5) Uani 1 1 d . . .
F1 F 0.7508(2) -0.0581(2) 0.15124(4) 0.0308(4) Uani 1 1 d . . .
F2 F 0.8894(2) 0.2066(2) 0.21958(4) 0.0343(4) Uani 1 1 d . . .
F3 F 0.6313(2) 0.6015(2) 0.23335(4) 0.0354(4) Uani 1 1 d . . .
F4 F 0.2257(2) 0.74013(19) 0.17975(4) 0.0279(3) Uani 1 1 d . . .
O1 O -0.3447(3) 0.6006(2) 0.04872(5) 0.0266(4) Uani 1 1 d . . .
O2 O -0.2580(3) 0.3050(2) 0.00554(5) 0.0257(4) Uani 1 1 d . . .
H1 H -0.024(4) 0.616(4) 0.1101(7) 0.024(6) Uiso 1 1 d . . .
H3 H 0.081(4) 0.057(3) 0.0389(7) 0.025(6) Uiso 1 1 d . . .
H4 H 0.437(4) -0.065(4) 0.0852(7) 0.029(6) Uiso 1 1 d . . .
H1O H -0.513(6) 0.630(5) 0.0247(10) 0.092(10) Uiso 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
C1 0.0219(12) 0.0195(12) 0.0186(12) 0.0015(9) -0.0009(9) 0.0015(9)
C2 0.0203(11) 0.0216(11) 0.0147(12) 0.0023(9) -0.0015(9) 0.0001(8)
C3 0.0267(13) 0.0234(12) 0.0190(13) -0.0032(10) -0.0022(10) 0.0011(9)
C4 0.0258(12) 0.0213(12) 0.0231(13) -0.0020(10) -0.0039(10) 0.0028(10)
C5 0.0212(11) 0.0228(12) 0.0170(12) 0.0041(9) -0.0008(9) -0.0011(9)
C6 0.0223(12) 0.0252(12) 0.0228(13) 0.0040(10) -0.0006(10) 0.0036(9)
C7 0.0185(11) 0.0353(14) 0.0216(13) 0.0089(11) -0.0039(10) 0.0006(10)
C8 0.0280(13) 0.0321(13) 0.0160(12) -0.0031(10) -0.0052(10) -0.0060(10)
C9 0.0245(12) 0.0229(12) 0.0208(13) 0.0001(10) -0.0016(10) 0.0018(9)
C10 0.0198(11) 0.0231(12) 0.0159(12) 0.0016(9) -0.0015(9) -0.0025(9)
C11 0.0219(11) 0.0231(12) 0.0171(12) 0.0012(10) -0.0003(9) 0.0012(9)
F1 0.0327(8) 0.0248(7) 0.0349(8) 0.0002(6) -0.0018(6) 0.0126(5)
F2 0.0295(7) 0.0476(9) 0.0255(8) 0.0043(6) -0.0119(6) 0.0057(6)
F3 0.0390(8) 0.0427(8) 0.0241(8) -0.0100(6) -0.0135(6) 0.0031(6)
F4 0.0306(7) 0.0247(7) 0.0280(8) -0.0054(5) -0.0100(6) 0.0073(5)
O1 0.0288(9) 0.0286(9) 0.0221(9) -0.0040(7) -0.0076(7) 0.0092(7)
O2 0.0292(9) 0.0305(9) 0.0173(9) -0.0046(7) -0.0069(7) 0.0041(7)

_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 1.373(3) . ?
C1 C10 1.414(3) . ?
C1 H1 0.94(2) . ?
C2 C3 1.410(3) . ?
C2 C11 1.480(3) . ?
C3 C4 1.360(3) . ?
C3 H3 0.94(2) . ?
C4 C5 1.412(3) . ?
C4 H4 0.96(2) . ?
C5 C6 1.408(3) . ?
C5 C10 1.419(3) . ?
C6 F1 1.349(2) . ?
C6 C7 1.358(3) . ?
C7 F2 1.345(2) . ?
C7 C8 1.396(3) . ?
C8 F3 1.338(2) . ?
C8 C9 1.360(3) . ?
C9 F4 1.352(2) . ?
C9 C10 1.403(3) . ?
C11 O2 1.245(2) . ?
C11 O1 1.300(2) . ?
O1 H1O 1.12(3) . ?

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 C10 120.4(2) . . ?
C2 C1 H1 119.3(12) . . ?
C10 C1 H1 120.3(12) . . ?
C1 C2 C3 120.32(19) . . ?
C1 C2 C11 120.70(19) . . ?
C3 C2 C11 118.98(19) . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3 123.5(12) . . ?
C2 C3 H3 115.8(12) . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 H4 119.6(12) . . ?
C5 C4 H4 119.9(12) . . ?
C6 C5 C4 122.31(19) . . ?
C6 C5 C10 118.23(19) . . ?
C4 C5 C10 119.45(18) . . ?
F1 C6 C7 118.81(18) . . ?
F1 C6 C5 119.54(19) . . ?
C7 C6 C5 121.6(2) . . ?
F2 C7 C6 120.8(2) . . ?
F2 C7 C8 119.3(2) . . ?
C6 C7 C8 119.95(19) . . ?
F3 C8 C9 121.3(2) . . ?
F3 C8 C7 118.58(18) . . ?
C9 C8 C7 120.1(2) . . ?
F4 C9 C8 118.46(19) . . ?
F4 C9 C10 120.02(18) . . ?
C8 C9 C10 121.5(2) . . ?
C9 C10 C1 122.6(2) . . ?
C9 C10 C5 118.56(18) . . ?
C1 C10 C5 118.83(19) . . ?
O2 C11 O1 122.97(18) . . ?
O2 C11 C2 120.45(19) . . ?
O1 C11 C2 116.58(18) . . ?
C11 O1 H1O 110.7(15) . . ?

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
C10 C1 C2 C3 -0.4(3) . . . . ?
C10 C1 C2 C11 -179.75(18) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C11 C2 C3 C4 -179.9(2) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C3 C4 C5 C6 -179.5(2) . . . . ?
C3 C4 C5 C10 0.1(3) . . . . ?
C4 C5 C6 F1 -0.4(3) . . . . ?
C10 C5 C6 F1 -179.95(18) . . . . ?
C4 C5 C6 C7 178.3(2) . . . . ?
C10 C5 C6 C7 -1.3(3) . . . . ?
F1 C6 C7 F2 -0.5(3) . . . . ?
C5 C6 C7 F2 -179.12(18) . . . . ?
F1 C6 C7 C8 -179.77(19) . . . . ?
C5 C6 C7 C8 1.6(3) . . . . ?
F2 C7 C8 F3 0.7(3) . . . . ?
C6 C7 C8 F3 180.0(2) . . . . ?
F2 C7 C8 C9 179.77(19) . . . . ?
C6 C7 C8 C9 -0.9(3) . . . . ?
F3 C8 C9 F4 -1.8(3) . . . . ?
C7 C8 C9 F4 179.14(19) . . . . ?
F3 C8 C9 C10 179.08(19) . . . . ?
C7 C8 C9 C10 0.0(3) . . . . ?
F4 C9 C10 C1 1.7(3) . . . . ?
C8 C9 C10 C1 -179.2(2) . . . . ?
F4 C9 C10 C5 -178.88(18) . . . . ?
C8 C9 C10 C5 0.2(3) . . . . ?
C2 C1 C10 C9 179.3(2) . . . . ?
C2 C1 C10 C5 -0.1(3) . . . . ?
C6 C5 C10 C9 0.4(3) . . . . ?
C4 C5 C10 C9 -179.2(2) . . . . ?
C6 C5 C10 C1 179.82(19) . . . . ?
C4 C5 C10 C1 0.2(3) . . . . ?
C1 C2 C11 O2 175.3(2) . . . . ?
C3 C2 C11 O2 -4.1(3) . . . . ?
C1 C2 C11 O1 -5.5(3) . . . . ?
C3 C2 C11 O1 175.13(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.929
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.355
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.058

data_cz7_295k
_database_code_depnum_ccdc_archive 'CCDC 697373'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H4 F4 O2'
_chemical_formula_sum            'C11 H4 F4 O2'
_chemical_formula_weight         244.14

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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                   5.053(2)
_cell_length_b                   5.884(2)
_cell_length_c                   31.085(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.830(10)
_cell_angle_gamma                90.00
_cell_volume                     923.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1682
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      23.91

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.757
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             488
_exptl_absorpt_coefficient_mu    0.173
_exptl_absorpt_correction_type   none

_exptl_special_details           
;
Air conditioned room
;

_diffrn_ambient_temperature      295(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  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_standards_decay_%        0.00
_diffrn_reflns_number            6629
_diffrn_reflns_av_R_equivalents  0.0774
_diffrn_reflns_av_sigmaI/netI    0.0529
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_theta_min         2.62
_diffrn_reflns_theta_max         25.49
_reflns_number_total             1716
_reflns_number_gt                1080
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    
;
M.C. Burla, M. Camalli, B. Carrozzini, G.L. Cascarano, C. Giacovazzo,
G. Polidori, R. Spagna (2003).
SIR2002: the program. J. Appl. Cryst. 36,1103
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEP-III (Burnett and Johnson, 1996), Mercury 1.4, CCDC'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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     
'w=1/[σ²(Fo²)+(0.0478P)²] 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         1716
_refine_ls_number_parameters     170
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0616
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.1014
_refine_ls_wR_factor_gt          0.0914
_refine_ls_goodness_of_fit_ref   0.946
_refine_ls_restrained_S_all      0.946
_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
C1 C 0.0710(4) 0.4752(3) 0.10544(6) 0.0454(5) Uani 1 1 d . . .
C2 C 0.0050(3) 0.3454(3) 0.06998(5) 0.0445(5) Uani 1 1 d . . .
C3 C 0.1415(4) 0.1424(4) 0.06271(7) 0.0558(6) Uani 1 1 d . . .
C4 C 0.3412(4) 0.0735(4) 0.09038(7) 0.0574(6) Uani 1 1 d . . .
C5 C 0.4144(4) 0.2033(3) 0.12706(6) 0.0458(5) Uani 1 1 d . . .
C6 C 0.6204(4) 0.1394(4) 0.15648(6) 0.0540(5) Uani 1 1 d . . .
C7 C 0.6906(4) 0.2679(4) 0.19112(7) 0.0577(6) Uani 1 1 d . . .
C8 C 0.5555(4) 0.4680(4) 0.19873(6) 0.0576(6) Uani 1 1 d . . .
C9 C 0.3547(4) 0.5351(3) 0.17144(6) 0.0524(5) Uani 1 1 d . . .
C10 C 0.2777(3) 0.4074(3) 0.13473(6) 0.0427(5) Uani 1 1 d . . .
C11 C -0.2115(4) 0.4166(3) 0.03927(6) 0.0480(5) Uani 1 1 d . . .
F1 F 0.7547(2) -0.0548(2) 0.14987(4) 0.0788(5) Uani 1 1 d . . .
F2 F 0.8904(2) 0.2053(2) 0.21858(4) 0.0848(5) Uani 1 1 d . . .
F3 F 0.6289(3) 0.5920(2) 0.23335(4) 0.0867(5) Uani 1 1 d . . .
F4 F 0.2247(2) 0.72929(19) 0.17987(4) 0.0718(4) Uani 1 1 d . . .
O1 O -0.3404(3) 0.5962(2) 0.04785(4) 0.0645(5) Uani 1 1 d . . .
O2 O -0.2618(3) 0.3002(3) 0.00617(4) 0.0648(4) Uani 1 1 d . . .
H1 H -0.020(4) 0.609(3) 0.1100(6) 0.056(6) Uiso 1 1 d . . .
H1O H -0.528(6) 0.642(5) 0.0217(10) 0.145(11) Uiso 1 1 d . . .
H3 H 0.087(4) 0.057(3) 0.0385(7) 0.066(6) Uiso 1 1 d . . .
H4 H 0.438(4) -0.057(4) 0.0848(6) 0.070(6) Uiso 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
C1 0.0468(11) 0.0464(12) 0.0422(11) -0.0007(9) -0.0048(9) 0.0072(9)
C2 0.0453(10) 0.0492(11) 0.0382(10) -0.0017(9) -0.0044(8) 0.0063(9)
C3 0.0610(13) 0.0571(13) 0.0481(12) -0.0109(11) -0.0103(10) 0.0093(10)
C4 0.0618(13) 0.0523(13) 0.0570(14) -0.0056(11) -0.0077(11) 0.0160(11)
C5 0.0446(10) 0.0496(11) 0.0429(11) 0.0050(9) -0.0014(9) 0.0042(9)
C6 0.0482(11) 0.0594(13) 0.0537(13) 0.0089(10) -0.0039(10) 0.0126(10)
C7 0.0434(11) 0.0801(16) 0.0482(13) 0.0120(11) -0.0110(9) 0.0060(10)
C8 0.0560(12) 0.0743(15) 0.0410(12) -0.0038(10) -0.0128(10) -0.0024(11)
C9 0.0534(12) 0.0556(13) 0.0474(12) -0.0041(10) -0.0071(10) 0.0059(10)
C10 0.0427(10) 0.0466(11) 0.0385(10) 0.0026(9) -0.0024(8) 0.0011(8)
C11 0.0482(11) 0.0550(13) 0.0403(11) -0.0040(10) -0.0034(9) 0.0064(10)
F1 0.0769(9) 0.0738(9) 0.0841(10) 0.0011(7) -0.0121(7) 0.0369(7)
F2 0.0650(8) 0.1176(11) 0.0684(9) 0.0099(7) -0.0297(7) 0.0192(7)
F3 0.0859(9) 0.1089(11) 0.0618(8) -0.0251(7) -0.0331(7) 0.0099(7)
F4 0.0789(8) 0.0654(8) 0.0682(8) -0.0209(6) -0.0255(7) 0.0226(6)
O1 0.0663(9) 0.0706(10) 0.0546(9) -0.0122(7) -0.0185(7) 0.0253(8)
O2 0.0672(9) 0.0782(10) 0.0468(8) -0.0172(7) -0.0189(7) 0.0194(7)

_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 1.369(2) . ?
C1 C10 1.409(2) . ?
C1 H1 0.92(2) . ?
C2 C3 1.404(3) . ?
C2 C11 1.476(2) . ?
C3 C4 1.356(3) . ?
C3 H3 0.94(2) . ?
C4 C5 1.407(3) . ?
C4 H4 0.93(2) . ?
C5 C6 1.403(2) . ?
C5 C10 1.411(3) . ?
C6 C7 1.349(3) . ?
C6 F1 1.350(2) . ?
C7 F2 1.341(2) . ?
C7 C8 1.387(3) . ?
C8 F3 1.338(2) . ?
C8 C9 1.349(2) . ?
C9 F4 1.350(2) . ?
C9 C10 1.405(3) . ?
C11 O2 1.252(2) . ?
C11 O1 1.277(2) . ?
O1 H1O 1.25(3) . ?

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 C10 120.38(18) . . ?
C2 C1 H1 119.6(11) . . ?
C10 C1 H1 120.0(11) . . ?
C1 C2 C3 120.16(17) . . ?
C1 C2 C11 120.39(17) . . ?
C3 C2 C11 119.44(17) . . ?
C4 C3 C2 120.60(19) . . ?
C4 C3 H3 121.9(12) . . ?
C2 C3 H3 117.5(12) . . ?
C3 C4 C5 120.6(2) . . ?
C3 C4 H4 120.7(12) . . ?
C5 C4 H4 118.6(12) . . ?
C6 C5 C4 122.66(18) . . ?
C6 C5 C10 118.13(18) . . ?
C4 C5 C10 119.20(17) . . ?
C7 C6 F1 118.79(16) . . ?
C7 C6 C5 121.85(19) . . ?
F1 C6 C5 119.35(18) . . ?
F2 C7 C6 120.94(19) . . ?
F2 C7 C8 119.07(19) . . ?
C6 C7 C8 119.99(17) . . ?
F3 C8 C9 121.10(19) . . ?
F3 C8 C7 118.75(17) . . ?
C9 C8 C7 120.16(18) . . ?
C8 C9 F4 118.93(18) . . ?
C8 C9 C10 121.58(19) . . ?
F4 C9 C10 119.49(16) . . ?
C9 C10 C1 122.69(18) . . ?
C9 C10 C5 118.29(16) . . ?
C1 C10 C5 119.02(17) . . ?
O2 C11 O1 122.66(16) . . ?
O2 C11 C2 119.36(18) . . ?
O1 C11 C2 117.98(16) . . ?
C11 O1 H1O 114.9(13) . . ?

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
C10 C1 C2 C3 0.5(3) . . . . ?
C10 C1 C2 C11 -179.97(17) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C11 C2 C3 C4 179.90(19) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
C3 C4 C5 C6 -179.7(2) . . . . ?
C3 C4 C5 C10 -0.2(3) . . . . ?
C4 C5 C6 C7 178.9(2) . . . . ?
C10 C5 C6 C7 -0.6(3) . . . . ?
C4 C5 C6 F1 -0.4(3) . . . . ?
C10 C5 C6 F1 -179.90(17) . . . . ?
F1 C6 C7 F2 0.2(3) . . . . ?
C5 C6 C7 F2 -179.13(18) . . . . ?
F1 C6 C7 C8 -179.84(19) . . . . ?
C5 C6 C7 C8 0.8(3) . . . . ?
F2 C7 C8 F3 -0.1(3) . . . . ?
C6 C7 C8 F3 179.91(19) . . . . ?
F2 C7 C8 C9 179.63(19) . . . . ?
C6 C7 C8 C9 -0.3(3) . . . . ?
F3 C8 C9 F4 -1.0(3) . . . . ?
C7 C8 C9 F4 179.29(18) . . . . ?
F3 C8 C9 C10 179.33(19) . . . . ?
C7 C8 C9 C10 -0.4(3) . . . . ?
C8 C9 C10 C1 -179.18(19) . . . . ?
F4 C9 C10 C1 1.1(3) . . . . ?
C8 C9 C10 C5 0.7(3) . . . . ?
F4 C9 C10 C5 -179.04(17) . . . . ?
C2 C1 C10 C9 179.51(18) . . . . ?
C2 C1 C10 C5 -0.3(3) . . . . ?
C6 C5 C10 C9 -0.2(3) . . . . ?
C4 C5 C10 C9 -179.70(19) . . . . ?
C6 C5 C10 C1 179.68(17) . . . . ?
C4 C5 C10 C1 0.1(3) . . . . ?
C1 C2 C11 O2 177.19(19) . . . . ?
C3 C2 C11 O2 -3.3(3) . . . . ?
C1 C2 C11 O1 -2.8(3) . . . . ?
C3 C2 C11 O1 176.66(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.036

data_cz10_295k
_database_code_depnum_ccdc_archive 'CCDC 697374'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H5 F4 N O'
_chemical_formula_sum            'C11 H5 F4 N O'
_chemical_formula_weight         243.16

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'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   4.9553(10)
_cell_length_b                   7.3353(15)
_cell_length_c                   13.504(3)
_cell_angle_alpha                96.420(10)
_cell_angle_beta                 97.360(10)
_cell_angle_gamma                100.810(10)
_cell_volume                     473.50(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    1143
_cell_measurement_theta_min      2.86
_cell_measurement_theta_max      25.13

_exptl_crystal_description       table
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.706
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             244
_exptl_absorpt_coefficient_mu    0.164
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker, 1997'
_exptl_absorpt_correction_T_min  0.743709
_exptl_absorpt_correction_T_max  1.000000

_exptl_special_details           
;
OXFORD low temperature device.

;

_diffrn_ambient_temperature      295(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  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_standards_decay_%        0.00
_diffrn_reflns_number            3650
_diffrn_reflns_av_R_equivalents  0.0140
_diffrn_reflns_av_sigmaI/netI    0.0211
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.85
_diffrn_reflns_theta_max         25.99
_reflns_number_total             1807
_reflns_number_gt                1297
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    
;
M.C. Burla, M. Camalli, B. Carrozzini, G.L. Cascarano, C. Giacovazzo,
G. Polidori, R. Spagna (2003).
SIR2002: the program. J. Appl. Cryst. 36,1103
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEP-III (Burnett and Johnson, 1996), Mercury 1.4, CCDC'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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     
'w=1/[σ²(Fo²)+(0.0582P)²+0.0315P] 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_number_reflns         1807
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0561
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.1093
_refine_ls_wR_factor_gt          0.0970
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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 1.1577(3) 1.49036(16) 0.71879(10) 0.0864(4) Uani 1 1 d . . .
F2 F 0.7200(3) 1.48597(18) 0.57705(10) 0.0985(5) Uani 1 1 d . . .
F3 F 0.2970(2) 1.18524(18) 0.53247(9) 0.0838(4) Uani 1 1 d . . .
F4 F 0.3077(2) 0.88176(17) 0.62790(9) 0.0739(4) Uani 1 1 d . . .
O1 O 1.2193(2) 0.68816(17) 0.94636(10) 0.0589(4) Uani 1 1 d . . .
N1 N 0.7538(3) 0.6010(2) 0.91933(12) 0.0510(4) Uani 1 1 d . . .
C1 C 0.7499(3) 0.8734(3) 0.78020(13) 0.0459(4) Uani 1 1 d . . .
C2 C 0.9698(3) 0.8761(2) 0.85358(12) 0.0437(4) Uani 1 1 d . . .
C3 C 1.1884(4) 1.0349(2) 0.87607(14) 0.0494(4) Uani 1 1 d . . .
C4 C 1.1840(4) 1.1857(3) 0.82737(14) 0.0537(5) Uani 1 1 d . . .
C5 C 0.9596(3) 1.1868(2) 0.75165(13) 0.0485(4) Uani 1 1 d . . .
C6 C 0.9471(4) 1.3403(3) 0.69847(15) 0.0599(5) Uani 1 1 d . . .
C7 C 0.7288(4) 1.3386(3) 0.62647(15) 0.0656(6) Uani 1 1 d . . .
C8 C 0.5114(4) 1.1823(3) 0.60298(13) 0.0621(5) Uani 1 1 d . . .
C9 C 0.5193(4) 1.0318(3) 0.65148(13) 0.0543(5) Uani 1 1 d . . .
C10 C 0.7405(3) 1.0272(2) 0.72731(12) 0.0464(4) Uani 1 1 d . . .
C11 C 0.9888(3) 0.7146(2) 0.91005(12) 0.0448(4) Uani 1 1 d . . .
H1 H 0.616(4) 0.772(3) 0.7627(13) 0.050(5) Uiso 1 1 d . . .
H3 H 1.337(4) 1.033(2) 0.9282(13) 0.057(5) Uiso 1 1 d . . .
H1N H 0.772(4) 0.514(3) 0.9599(14) 0.055(5) Uiso 1 1 d . . .
H2N H 0.598(4) 0.637(3) 0.9047(15) 0.075(6) Uiso 1 1 d . . .
H4 H 1.334(3) 1.293(2) 0.8432(12) 0.050(5) Uiso 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
F1 0.0978(9) 0.0540(7) 0.1002(9) 0.0295(6) -0.0010(7) -0.0030(6)
F2 0.1264(11) 0.0795(9) 0.0977(10) 0.0499(7) -0.0013(8) 0.0318(8)
F3 0.0815(9) 0.1035(10) 0.0713(8) 0.0318(7) -0.0099(6) 0.0346(7)
F4 0.0553(7) 0.0831(8) 0.0763(8) 0.0229(6) -0.0118(5) 0.0043(6)
O1 0.0340(6) 0.0683(8) 0.0829(9) 0.0361(7) 0.0089(5) 0.0168(5)
N1 0.0349(8) 0.0539(9) 0.0691(10) 0.0269(8) 0.0068(7) 0.0115(7)
C1 0.0376(9) 0.0466(10) 0.0537(10) 0.0119(8) 0.0051(7) 0.0080(8)
C2 0.0379(8) 0.0464(9) 0.0506(9) 0.0122(7) 0.0093(7) 0.0135(7)
C3 0.0409(9) 0.0520(10) 0.0542(10) 0.0128(8) 0.0010(8) 0.0082(8)
C4 0.0487(10) 0.0473(11) 0.0613(11) 0.0113(8) 0.0023(8) 0.0019(8)
C5 0.0520(10) 0.0466(10) 0.0500(9) 0.0104(7) 0.0095(8) 0.0143(8)
C6 0.0701(13) 0.0486(11) 0.0628(11) 0.0155(9) 0.0106(9) 0.0118(9)
C7 0.0835(14) 0.0584(12) 0.0633(12) 0.0250(10) 0.0108(11) 0.0266(11)
C8 0.0642(12) 0.0774(14) 0.0515(11) 0.0196(10) 0.0024(9) 0.0295(11)
C9 0.0477(10) 0.0621(12) 0.0532(10) 0.0126(9) 0.0031(8) 0.0122(9)
C10 0.0452(9) 0.0487(10) 0.0486(9) 0.0112(7) 0.0092(7) 0.0143(8)
C11 0.0374(9) 0.0507(10) 0.0509(9) 0.0130(8) 0.0087(7) 0.0164(7)

_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 C6 1.343(2) . ?
F2 C7 1.337(2) . ?
F3 C8 1.338(2) . ?
F4 C9 1.348(2) . ?
O1 C11 1.2421(18) . ?
N1 C11 1.328(2) . ?
N1 H1N 0.895(19) . ?
N1 H2N 0.87(2) . ?
C1 C2 1.371(2) . ?
C1 C10 1.406(2) . ?
C1 H1 0.883(18) . ?
C2 C3 1.409(2) . ?
C2 C11 1.490(2) . ?
C3 C4 1.351(3) . ?
C3 H3 0.953(18) . ?
C4 C5 1.413(2) . ?
C4 H4 0.958(18) . ?
C5 C6 1.408(3) . ?
C5 C10 1.416(2) . ?
C6 C7 1.356(3) . ?
C7 C8 1.394(3) . ?
C8 C9 1.349(3) . ?
C9 C10 1.409(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
C11 N1 H1N 115.3(11) . . ?
C11 N1 H2N 118.4(14) . . ?
H1N N1 H2N 122.7(18) . . ?
C2 C1 C10 120.69(17) . . ?
C2 C1 H1 120.5(11) . . ?
C10 C1 H1 118.7(11) . . ?
C1 C2 C3 119.54(16) . . ?
C1 C2 C11 122.16(15) . . ?
C3 C2 C11 118.29(14) . . ?
C4 C3 C2 121.19(17) . . ?
C4 C3 H3 121.3(11) . . ?
C2 C3 H3 117.5(11) . . ?
C3 C4 C5 120.44(17) . . ?
C3 C4 H4 120.3(10) . . ?
C5 C4 H4 119.2(10) . . ?
C6 C5 C4 122.43(17) . . ?
C6 C5 C10 118.61(16) . . ?
C4 C5 C10 118.96(15) . . ?
F1 C6 C7 119.45(17) . . ?
F1 C6 C5 119.17(17) . . ?
C7 C6 C5 121.37(18) . . ?
F2 C7 C6 120.51(19) . . ?
F2 C7 C8 119.32(18) . . ?
C6 C7 C8 120.17(17) . . ?
F3 C8 C9 121.18(19) . . ?
F3 C8 C7 118.92(17) . . ?
C9 C8 C7 119.90(17) . . ?
F4 C9 C8 119.20(16) . . ?
F4 C9 C10 118.68(15) . . ?
C8 C9 C10 122.11(17) . . ?
C1 C10 C9 123.00(16) . . ?
C1 C10 C5 119.17(15) . . ?
C9 C10 C5 117.83(16) . . ?
O1 C11 N1 121.74(15) . . ?
O1 C11 C2 120.25(14) . . ?
N1 C11 C2 118.00(14) . . ?

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

C10 C1 C2 C3 0.0(3) . . . . ?
C10 C1 C2 C11 -179.04(14) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C11 C2 C3 C4 179.82(16) . . . . ?
C2 C3 C4 C5 -0.6(3) . . . . ?
C3 C4 C5 C6 -179.57(17) . . . . ?
C3 C4 C5 C10 -0.3(3) . . . . ?
C4 C5 C6 F1 1.2(3) . . . . ?
C10 C5 C6 F1 -178.05(15) . . . . ?
C4 C5 C6 C7 -179.62(17) . . . . ?
C10 C5 C6 C7 1.1(3) . . . . ?
F1 C6 C7 F2 -1.1(3) . . . . ?
C5 C6 C7 F2 179.72(17) . . . . ?
F1 C6 C7 C8 178.63(17) . . . . ?
C5 C6 C7 C8 -0.6(3) . . . . ?
F2 C7 C8 F3 -1.1(3) . . . . ?
C6 C7 C8 F3 179.22(17) . . . . ?
F2 C7 C8 C9 179.23(17) . . . . ?
C6 C7 C8 C9 -0.5(3) . . . . ?
F3 C8 C9 F4 0.3(3) . . . . ?
C7 C8 C9 F4 -179.97(16) . . . . ?
F3 C8 C9 C10 -178.76(16) . . . . ?
C7 C8 C9 C10 1.0(3) . . . . ?
C2 C1 C10 C9 -179.85(15) . . . . ?
C2 C1 C10 C5 -0.9(3) . . . . ?
F4 C9 C10 C1 -0.5(3) . . . . ?
C8 C9 C10 C1 178.62(17) . . . . ?
F4 C9 C10 C5 -179.43(15) . . . . ?
C8 C9 C10 C5 -0.4(3) . . . . ?
C6 C5 C10 C1 -179.69(15) . . . . ?
C4 C5 C10 C1 1.0(3) . . . . ?
C6 C5 C10 C9 -0.7(3) . . . . ?
C4 C5 C10 C9 -179.95(16) . . . . ?
C1 C2 C11 O1 153.23(17) . . . . ?
C3 C2 C11 O1 -25.8(2) . . . . ?
C1 C2 C11 N1 -26.3(2) . . . . ?
C3 C2 C11 N1 154.59(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.143
_refine_diff_density_min         -0.159
_refine_diff_density_rms         0.033


data_cz10_93k
_database_code_depnum_ccdc_archive 'CCDC 697375'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H5 F4 N O'
_chemical_formula_sum            'C11 H5 F4 N O'
_chemical_formula_weight         243.16

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'
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   4.9386(14)
_cell_length_b                   7.250(2)
_cell_length_c                   13.210(4)
_cell_angle_alpha                97.630(10)
_cell_angle_beta                 96.440(10)
_cell_angle_gamma                100.470(10)
_cell_volume                     456.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    954
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      27.46

_exptl_crystal_description       table
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.56
_exptl_crystal_size_mid          0.46
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.769
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             244
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker, 1997'
_exptl_absorpt_correction_T_min  0.718937
_exptl_absorpt_correction_T_max  1.000000

_exptl_special_details           
;
OXFORD low temperature device.
;

_diffrn_ambient_temperature      93(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  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_standards_decay_%        0.00
_diffrn_reflns_number            3898
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0414
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.89
_diffrn_reflns_theta_max         27.49
_reflns_number_total             2002
_reflns_number_gt                1393
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    
;
M.C. Burla, M. Camalli, B. Carrozzini, G.L. Cascarano, C. Giacovazzo,
G. Polidori, R. Spagna (2003).
SIR2002: the program. J. Appl. Cryst. 36,1103
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    
'ORTEP-III (Burnett and Johnson, 1996), Mercury 1.4, CCDC'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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     
'w=1/[σ²(Fo²)+(0.0801P)²] 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_number_reflns         2002
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0722
_refine_ls_R_factor_gt           0.0489
_refine_ls_wR_factor_ref         0.1422
_refine_ls_wR_factor_gt          0.1250
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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 1.1669(3) 1.49627(17) 0.71651(10) 0.0339(4) Uani 1 1 d . . .
F2 F 0.7267(3) 1.49253(18) 0.57456(10) 0.0364(4) Uani 1 1 d . . .
F3 F 0.2989(2) 1.19107(17) 0.53116(9) 0.0320(4) Uani 1 1 d . . .
F4 F 0.3096(2) 0.88368(17) 0.62635(9) 0.0300(3) Uani 1 1 d . . .
O1 O 1.2226(3) 0.6886(2) 0.94687(11) 0.0265(4) Uani 1 1 d . . .
N1 N 0.7557(4) 0.5995(3) 0.91809(14) 0.0235(4) Uani 1 1 d . . .
C1 C 0.7529(4) 0.8746(3) 0.77928(16) 0.0220(5) Uani 1 1 d . . .
C2 C 0.9733(4) 0.8777(3) 0.85287(16) 0.0228(5) Uani 1 1 d . . .
C3 C 1.1949(4) 1.0371(3) 0.87598(16) 0.0229(5) Uani 1 1 d . . .
C4 C 1.1918(4) 1.1898(3) 0.82648(16) 0.0251(5) Uani 1 1 d . . .
C5 C 0.9662(4) 1.1907(3) 0.75022(16) 0.0229(5) Uani 1 1 d . . .
C6 C 0.9545(4) 1.3449(3) 0.69634(17) 0.0260(5) Uani 1 1 d . . .
C7 C 0.7352(5) 1.3441(3) 0.62425(16) 0.0274(5) Uani 1 1 d . . .
C8 C 0.5155(4) 1.1873(3) 0.60104(15) 0.0259(5) Uani 1 1 d . . .
C9 C 0.5227(4) 1.0344(3) 0.65012(16) 0.0243(5) Uani 1 1 d . . .
C10 C 0.7453(4) 1.0299(3) 0.72591(15) 0.0219(5) Uani 1 1 d . . .
C11 C 0.9925(4) 0.7145(3) 0.90994(15) 0.0223(5) Uani 1 1 d . . .
H1 H 0.627(5) 0.773(3) 0.7640(16) 0.020(6) Uiso 1 1 d . . .
H3 H 1.344(4) 1.033(3) 0.9285(16) 0.021(5) Uiso 1 1 d . . .
H1N H 0.774(5) 0.513(3) 0.9566(18) 0.025(6) Uiso 1 1 d . . .
H2N H 0.605(5) 0.638(3) 0.9056(18) 0.030(6) Uiso 1 1 d . . .
H4 H 1.350(4) 1.298(3) 0.8421(15) 0.017(5) Uiso 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
F1 0.0345(8) 0.0238(7) 0.0406(8) 0.0079(6) -0.0007(6) 0.0000(6)
F2 0.0421(8) 0.0297(8) 0.0394(8) 0.0141(6) -0.0007(6) 0.0101(6)
F3 0.0283(7) 0.0376(8) 0.0314(7) 0.0083(6) -0.0017(5) 0.0114(6)
F4 0.0225(7) 0.0304(7) 0.0348(7) 0.0057(5) -0.0009(5) 0.0022(5)
O1 0.0169(7) 0.0301(9) 0.0341(8) 0.0097(7) 0.0030(6) 0.0057(6)
N1 0.0165(9) 0.0233(10) 0.0324(10) 0.0085(8) 0.0022(7) 0.0061(7)
C1 0.0175(11) 0.0208(11) 0.0267(11) -0.0007(9) 0.0039(8) 0.0038(9)
C2 0.0199(10) 0.0242(11) 0.0257(11) 0.0023(9) 0.0067(8) 0.0071(8)
C3 0.0179(10) 0.0256(11) 0.0247(11) 0.0016(9) 0.0026(8) 0.0047(8)
C4 0.0214(11) 0.0227(11) 0.0290(12) -0.0018(9) 0.0036(9) 0.0029(9)
C5 0.0229(11) 0.0220(11) 0.0245(10) 0.0007(8) 0.0066(8) 0.0063(9)
C6 0.0267(12) 0.0206(11) 0.0304(12) 0.0017(9) 0.0080(9) 0.0027(9)
C7 0.0324(12) 0.0240(11) 0.0287(12) 0.0073(9) 0.0063(10) 0.0095(10)
C8 0.0238(11) 0.0329(12) 0.0225(11) 0.0024(9) 0.0020(8) 0.0119(9)
C9 0.0195(10) 0.0278(12) 0.0248(11) 0.0010(9) 0.0047(8) 0.0038(9)
C10 0.0192(10) 0.0235(11) 0.0239(11) 0.0014(8) 0.0067(8) 0.0058(9)
C11 0.0201(11) 0.0254(11) 0.0217(10) -0.0002(8) 0.0035(8) 0.0074(9)

_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 C6 1.348(2) . ?
F2 C7 1.337(2) . ?
F3 C8 1.339(2) . ?
F4 C9 1.348(2) . ?
O1 C11 1.242(2) . ?
N1 C11 1.331(3) . ?
N1 H1N 0.87(2) . ?
N1 H2N 0.85(2) . ?
C1 C2 1.370(3) . ?
C1 C10 1.409(3) . ?
C1 H1 0.86(2) . ?
C2 C3 1.414(3) . ?
C2 C11 1.496(3) . ?
C3 C4 1.360(3) . ?
C3 H3 0.96(2) . ?
C4 C5 1.417(3) . ?
C4 H4 0.98(2) . ?
C5 C6 1.409(3) . ?
C5 C10 1.419(3) . ?
C6 C7 1.358(3) . ?
C7 C8 1.396(3) . ?
C8 C9 1.360(3) . ?
C9 C10 1.410(3) . ?

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
C11 N1 H1N 114.7(15) . . ?
C11 N1 H2N 118.2(16) . . ?
H1N N1 H2N 123(2) . . ?
C2 C1 C10 120.4(2) . . ?
C2 C1 H1 117.9(14) . . ?
C10 C1 H1 121.6(14) . . ?
C1 C2 C3 120.18(19) . . ?
C1 C2 C11 122.16(19) . . ?
C3 C2 C11 117.65(18) . . ?
C4 C3 C2 120.7(2) . . ?
C4 C3 H3 121.9(13) . . ?
C2 C3 H3 117.3(12) . . ?
C3 C4 C5 120.3(2) . . ?
C3 C4 H4 119.7(12) . . ?
C5 C4 H4 120.0(11) . . ?
C6 C5 C4 122.4(2) . . ?
C6 C5 C10 118.51(19) . . ?
C4 C5 C10 119.08(19) . . ?
F1 C6 C7 119.29(18) . . ?
F1 C6 C5 119.13(19) . . ?
C7 C6 C5 121.6(2) . . ?
F2 C7 C6 120.70(19) . . ?
F2 C7 C8 119.18(18) . . ?
C6 C7 C8 120.12(19) . . ?
F3 C8 C9 121.1(2) . . ?
F3 C8 C7 119.11(18) . . ?
C9 C8 C7 119.83(19) . . ?
F4 C9 C8 119.06(18) . . ?
F4 C9 C10 119.05(18) . . ?
C8 C9 C10 121.9(2) . . ?
C1 C10 C9 122.6(2) . . ?
C1 C10 C5 119.32(19) . . ?
C9 C10 C5 118.05(19) . . ?
O1 C11 N1 122.21(18) . . ?
O1 C11 C2 120.35(18) . . ?
N1 C11 C2 117.43(18) . . ?

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
C10 C1 C2 C3 0.1(3) . . . . ?
C10 C1 C2 C11 -178.81(18) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
C11 C2 C3 C4 179.55(18) . . . . ?
C2 C3 C4 C5 -0.4(3) . . . . ?
C3 C4 C5 C6 -179.5(2) . . . . ?
C3 C4 C5 C10 -0.4(3) . . . . ?
C4 C5 C6 F1 1.1(3) . . . . ?
C10 C5 C6 F1 -178.07(17) . . . . ?
C4 C5 C6 C7 -179.3(2) . . . . ?
C10 C5 C6 C7 1.6(3) . . . . ?
F1 C6 C7 F2 -0.9(3) . . . . ?
C5 C6 C7 F2 179.41(19) . . . . ?
F1 C6 C7 C8 178.91(19) . . . . ?
C5 C6 C7 C8 -0.7(3) . . . . ?
F2 C7 C8 F3 -1.4(3) . . . . ?
C6 C7 C8 F3 178.72(19) . . . . ?
F2 C7 C8 C9 179.25(18) . . . . ?
C6 C7 C8 C9 -0.6(3) . . . . ?
F3 C8 C9 F4 1.1(3) . . . . ?
C7 C8 C9 F4 -179.61(18) . . . . ?
F3 C8 C9 C10 -178.25(18) . . . . ?
C7 C8 C9 C10 1.1(3) . . . . ?
C2 C1 C10 C9 -179.53(19) . . . . ?
C2 C1 C10 C5 -0.9(3) . . . . ?
F4 C9 C10 C1 -0.9(3) . . . . ?
C8 C9 C10 C1 178.4(2) . . . . ?
F4 C9 C10 C5 -179.51(17) . . . . ?
C8 C9 C10 C5 -0.2(3) . . . . ?
C6 C5 C10 C1 -179.76(18) . . . . ?
C4 C5 C10 C1 1.1(3) . . . . ?
C6 C5 C10 C9 -1.1(3) . . . . ?
C4 C5 C10 C9 179.73(19) . . . . ?
C1 C2 C11 O1 154.4(2) . . . . ?
C3 C2 C11 O1 -24.6(3) . . . . ?
C1 C2 C11 N1 -25.0(3) . . . . ?
C3 C2 C11 N1 156.10(19) . . . . ?

_diffrn_measured_fraction_theta_max 0.947
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.947
_refine_diff_density_max         0.294
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.067

