Electronic Supplementary Material for CrystEngComm
This journal is (c) The Royal Society of Chemistry 2008

data_global
_journal_name_full               CrystEngComm
_journal_coden_Cambridge         1350

_publ_contact_author_name        'Prof. Dr. Edwin Weber'
_publ_contact_author_address     
; Institut fur Organische Chemie
TU Bergakademie Freiberg
Leipziger Strasse 29
D-09596 Freiberg/Sachsen
Germany
;
_publ_contact_author_email       edwin.weber@chemie.tu-freiberg.de
_publ_contact_author_fax         '49(03731) 392386'
_publ_contact_author_phone       '49(03731) 393170'

_publ_section_title              
; Crystalline packings of diketoarylhydrazones controlled by a methyl
for trifluoromethyl structural change
;

loop_
_publ_author_name
_publ_author_address
J.Marten
; Institut fur Organische Chemie
TU Bergakademie Freiberg
Leipziger Strasse 29
D-09596 Freiberg/Sachsen
Germany
;
W.Seichter
; Institut fur Organische Chemie
TU Bergakademie Freiberg
Leipziger Strasse 29
D-09596 Freiberg/Sachsen
Germany
;
E.Weber
; Institut fur Organische Chemie
TU Bergakademie Freiberg
Leipziger Strasse 29
D-09596 Freiberg/Sachsen
Germany
;
U.Bohme
; Institut fur Organische Chemie
TU Bergakademie Freiberg
Leipziger Strasse 29
D-09596 Freiberg/Sachsen
Germany
;

# TEXT

_publ_section_abstract           
; Three new hydrazone compounds having a p-iodoaryl and
diketohydrazone molecular skeleton in common but feature a
gradual replacement of the two methyl for trifluoromethyl
terminal groups were prepared and comparatively studied with
regard to their crystal structures. A quantum chemical calculation
of the single trifluoromethyl modified compound was undertaken to
decide on to low energy conformation referring to the hydrogen
bonded ring site. While the molecular structures of the compounds
remain rather unimpaired by the fluorine substitution, their
crystalline packings are markedly affected, showing a distinct
supramolecular control in the crystal lattices.
;

data_jama_8_0m
_database_code_depnum_ccdc_archive 'CCDC 661391'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H8 F3 I N2 O2'
_chemical_formula_weight         384.09

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   19.8553(5)
_cell_length_b                   7.8980(2)
_cell_length_c                   17.0579(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.9040(10)
_cell_angle_gamma                90.00
_cell_volume                     2660.78(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    153(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       irregular
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.58
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.39
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.918
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1472
_exptl_absorpt_coefficient_mu    2.441
_exptl_absorpt_correction_type   'multi scan'
_exptl_absorpt_correction_T_min  0.3317
_exptl_absorpt_correction_T_max  0.4494
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2002)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      153(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        none
_diffrn_reflns_number            31049
_diffrn_reflns_av_R_equivalents  0.0248
_diffrn_reflns_av_sigmaI/netI    0.0219
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.06
_diffrn_reflns_theta_max         37.71
_reflns_number_total             7084
_reflns_number_gt                3615
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART APEX2 (Bruker-AXS)'
_computing_cell_refinement       'SAINT-NT (Bruker, 2003)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_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^)+(0.0426P)^2^+4.0122P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7084
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.1143
_refine_ls_wR_factor_gt          0.0930
_refine_ls_goodness_of_fit_ref   0.918
_refine_ls_restrained_S_all      0.918
_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
I1 I 1.098526(10) 0.91297(3) 1.190525(11) 0.07107(9) Uani 1 1 d . . .
F1 F 0.78231(14) 0.4079(3) 0.95769(12) 0.1121(9) Uani 1 1 d . . .
F2 F 0.68538(12) 0.4614(5) 0.89633(17) 0.1427(12) Uani 1 1 d . . .
F3 F 0.75480(13) 0.6601(4) 0.92806(14) 0.1081(8) Uani 1 1 d . . .
O1 O 0.74059(11) 0.3996(3) 0.77365(13) 0.0809(7) Uani 1 1 d . . .
O2 O 0.92578(11) 0.6092(3) 0.72719(12) 0.0760(6) Uani 1 1 d . . .
N1 N 0.87823(10) 0.5950(2) 0.87670(11) 0.0459(4) Uani 1 1 d . . .
N2 N 0.93956(10) 0.6509(3) 0.87855(12) 0.0501(4) Uani 1 1 d . . .
H2 H 0.9539(15) 0.656(4) 0.8348(19) 0.060(8) Uiso 1 1 d . . .
C1 C 0.75038(16) 0.5030(6) 0.90227(19) 0.0812(9) Uani 1 1 d . . .
C2 C 0.77687(12) 0.4783(4) 0.82161(14) 0.0549(5) Uani 1 1 d . . .
C3 C 0.84327(11) 0.5463(3) 0.81021(12) 0.0462(4) Uani 1 1 d . . .
C4 C 0.86781(13) 0.5577(3) 0.73165(14) 0.0543(5) Uani 1 1 d . . .
C5 C 0.82374(16) 0.5152(5) 0.65872(16) 0.0743(8) Uani 1 1 d . . .
H5A H 0.8451 0.5542 0.6127 0.111 Uiso 1 1 calc R . .
H5B H 0.7798 0.5710 0.6597 0.111 Uiso 1 1 calc R . .
H5C H 0.8172 0.3923 0.6556 0.111 Uiso 1 1 calc R . .
C6 C 0.97381(11) 0.7069(3) 0.94995(12) 0.0466(4) Uani 1 1 d . . .
C7 C 0.94553(14) 0.6928(4) 1.02049(14) 0.0588(6) Uani 1 1 d . . .
H7 H 0.9018 0.6448 1.0215 0.071 Uiso 1 1 calc R . .
C8 C 0.98106(14) 0.7487(4) 1.08934(14) 0.0625(6) Uani 1 1 d . . .
H8 H 0.9621 0.7379 1.1380 0.075 Uiso 1 1 calc R . .
C9 C 1.04422(12) 0.8203(3) 1.08748(14) 0.0521(5) Uani 1 1 d . . .
C10 C 1.07230(13) 0.8349(4) 1.01726(16) 0.0605(6) Uani 1 1 d . . .
H10 H 1.1159 0.8839 1.0163 0.073 Uiso 1 1 calc R . .
C11 C 1.03709(13) 0.7784(4) 0.94852(15) 0.0586(6) Uani 1 1 d . . .
H11 H 1.0564 0.7886 0.9000 0.070 Uiso 1 1 calc 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
I1 0.07922(14) 0.06381(13) 0.06445(12) -0.00449(8) -0.02019(9) 0.00141(8)
F1 0.1204(18) 0.154(2) 0.0626(11) 0.0443(13) 0.0130(11) -0.0107(15)
F2 0.0676(12) 0.260(4) 0.1065(17) -0.004(2) 0.0372(12) -0.0362(18)
F3 0.1075(16) 0.129(2) 0.0930(15) -0.0218(15) 0.0362(13) 0.0270(15)
O1 0.0650(12) 0.1085(19) 0.0660(12) 0.0094(11) -0.0082(9) -0.0237(11)
O2 0.0669(12) 0.1135(19) 0.0501(10) -0.0077(10) 0.0186(9) -0.0180(11)
N1 0.0512(9) 0.0438(9) 0.0424(8) 0.0032(7) 0.0037(7) 0.0015(7)
N2 0.0569(11) 0.0532(10) 0.0410(9) -0.0005(8) 0.0084(8) -0.0033(9)
C1 0.0622(17) 0.122(3) 0.0621(17) 0.0089(19) 0.0174(13) -0.0021(18)
C2 0.0494(11) 0.0651(15) 0.0494(11) 0.0122(11) 0.0011(9) 0.0011(10)
C3 0.0498(11) 0.0482(11) 0.0404(9) 0.0013(8) 0.0040(8) 0.0036(9)
C4 0.0618(14) 0.0589(14) 0.0427(10) -0.0036(10) 0.0080(9) 0.0018(11)
C5 0.0805(19) 0.098(2) 0.0449(12) -0.0133(14) 0.0073(12) -0.0084(17)
C6 0.0533(11) 0.0438(10) 0.0424(9) 0.0006(8) 0.0035(8) 0.0007(9)
C7 0.0629(14) 0.0695(16) 0.0443(11) 0.0024(11) 0.0065(10) -0.0195(12)
C8 0.0704(15) 0.0746(17) 0.0428(10) 0.0011(11) 0.0077(10) -0.0163(13)
C9 0.0586(12) 0.0465(12) 0.0490(11) 0.0006(9) -0.0044(9) 0.0017(9)
C10 0.0467(12) 0.0695(16) 0.0655(15) -0.0062(13) 0.0069(10) -0.0062(11)
C11 0.0540(13) 0.0716(16) 0.0520(12) -0.0040(11) 0.0137(10) -0.0036(11)

_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
I1 C9 2.097(2) . ?
F1 C1 1.318(4) . ?
F2 C1 1.326(4) . ?
F3 C1 1.317(5) . ?
O1 C2 1.206(3) . ?
O2 C4 1.230(3) . ?
N1 N2 1.293(3) . ?
N1 C3 1.324(3) . ?
N2 C6 1.404(3) . ?
C1 C2 1.535(4) . ?
C2 C3 1.455(3) . ?
C3 C4 1.475(3) . ?
C4 C5 1.484(4) . ?
C6 C11 1.380(3) . ?
C6 C7 1.384(3) . ?
C7 C8 1.379(3) . ?
C8 C9 1.379(4) . ?
C9 C10 1.377(4) . ?
C10 C11 1.376(4) . ?

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
N2 N1 C3 121.97(19) . . ?
N1 N2 C6 119.99(19) . . ?
F3 C1 F1 106.7(3) . . ?
F3 C1 F2 106.9(3) . . ?
F1 C1 F2 107.8(3) . . ?
F3 C1 C2 113.7(3) . . ?
F1 C1 C2 112.8(3) . . ?
F2 C1 C2 108.7(3) . . ?
O1 C2 C3 125.9(2) . . ?
O1 C2 C1 116.0(3) . . ?
C3 C2 C1 118.2(2) . . ?
N1 C3 C2 113.26(19) . . ?
N1 C3 C4 124.6(2) . . ?
C2 C3 C4 122.2(2) . . ?
O2 C4 C3 118.4(2) . . ?
O2 C4 C5 119.8(2) . . ?
C3 C4 C5 121.8(2) . . ?
C11 C6 C7 120.0(2) . . ?
C11 C6 N2 118.3(2) . . ?
C7 C6 N2 121.7(2) . . ?
C8 C7 C6 119.8(2) . . ?
C7 C8 C9 119.9(2) . . ?
C10 C9 C8 120.3(2) . . ?
C10 C9 I1 118.72(18) . . ?
C8 C9 I1 120.95(18) . . ?
C11 C10 C9 119.9(2) . . ?
C10 C11 C6 120.1(2) . . ?

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
C3 N1 N2 C6 177.7(2) . . . . ?
F3 C1 C2 O1 -132.1(3) . . . . ?
F1 C1 C2 O1 106.3(3) . . . . ?
F2 C1 C2 O1 -13.2(5) . . . . ?
F3 C1 C2 C3 49.7(4) . . . . ?
F1 C1 C2 C3 -71.9(4) . . . . ?
F2 C1 C2 C3 168.5(3) . . . . ?
N2 N1 C3 C2 176.6(2) . . . . ?
N2 N1 C3 C4 -3.3(4) . . . . ?
O1 C2 C3 N1 -166.3(3) . . . . ?
C1 C2 C3 N1 11.8(4) . . . . ?
O1 C2 C3 C4 13.6(4) . . . . ?
C1 C2 C3 C4 -168.4(3) . . . . ?
N1 C3 C4 O2 3.2(4) . . . . ?
C2 C3 C4 O2 -176.6(3) . . . . ?
N1 C3 C4 C5 -174.4(3) . . . . ?
C2 C3 C4 C5 5.7(4) . . . . ?
N1 N2 C6 C11 -174.9(2) . . . . ?
N1 N2 C6 C7 4.7(4) . . . . ?
C11 C6 C7 C8 -0.7(4) . . . . ?
N2 C6 C7 C8 179.7(3) . . . . ?
C6 C7 C8 C9 0.8(4) . . . . ?
C7 C8 C9 C10 -0.6(4) . . . . ?
C7 C8 C9 I1 178.2(2) . . . . ?
C8 C9 C10 C11 0.2(4) . . . . ?
I1 C9 C10 C11 -178.6(2) . . . . ?
C9 C10 C11 C6 -0.1(4) . . . . ?
C7 C6 C11 C10 0.3(4) . . . . ?
N2 C6 C11 C10 180.0(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        37.71
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.924
_refine_diff_density_min         -0.894
_refine_diff_density_rms         0.070

data_jama13new
_database_code_depnum_ccdc_archive 'CCDC 661392'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H11 I N2 O2'
_chemical_formula_weight         330.12

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'
I I -0.4742 1.8119 '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                   7.9355(3)
_cell_length_b                   7.9685(3)
_cell_length_c                   11.1563(5)
_cell_angle_alpha                88.762(2)
_cell_angle_beta                 81.264(2)
_cell_angle_gamma                61.6120(10)
_cell_volume                     612.39(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.790
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    2.602
_exptl_absorpt_correction_type   'multi scan'
_exptl_absorpt_correction_T_min  0.6320
_exptl_absorpt_correction_T_max  0.8780
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2002)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        none
_diffrn_reflns_number            23617
_diffrn_reflns_av_R_equivalents  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0189
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.85
_diffrn_reflns_theta_max         34.84
_reflns_number_total             5306
_reflns_number_gt                3282
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART APEX2 (Bruker-AXS)'
_computing_cell_refinement       'SAINT-NT (Bruker, 2003)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_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^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5306
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0744
_refine_ls_R_factor_gt           0.0491
_refine_ls_wR_factor_ref         0.1973
_refine_ls_wR_factor_gt          0.1781
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_restrained_S_all      1.093
_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
I1 I 0.32193(4) -0.46677(4) 1.30451(2) 0.07499(16) Uani 1 1 d . . .
O1 O 0.2666(6) 0.2499(6) 0.5124(3) 0.0876(10) Uani 1 1 d . . .
O2 O 0.1451(8) 0.4860(5) 0.8655(3) 0.0950(12) Uani 1 1 d . . .
N1 N 0.2345(4) 0.1102(4) 0.8073(2) 0.0499(5) Uani 1 1 d . . .
N2 N 0.2257(5) 0.1460(4) 0.9218(2) 0.0549(6) Uani 1 1 d . . .
H2 H 0.2028 0.2597 0.9473 0.066 Uiso 1 1 calc R . .
C1 C 0.2331(9) -0.0173(8) 0.5807(4) 0.0839(14) Uani 1 1 d . . .
H1A H 0.2228 -0.0327 0.4957 0.126 Uiso 1 1 calc R . .
H1B H 0.1201 -0.0125 0.6336 0.126 Uiso 1 1 calc R . .
H1C H 0.3518 -0.1256 0.6002 0.126 Uiso 1 1 calc R . .
C2 C 0.2401(5) 0.1646(5) 0.6002(3) 0.0563(7) Uani 1 1 d . . .
C3 C 0.2123(5) 0.2403(5) 0.7271(3) 0.0527(6) Uani 1 1 d . . .
C4 C 0.1646(7) 0.4370(6) 0.7581(4) 0.0645(9) Uani 1 1 d . . .
C5 C 0.1273(8) 0.5846(7) 0.6646(4) 0.0780(13) Uani 1 1 d . . .
H5A H 0.0693 0.7117 0.7056 0.117 Uiso 1 1 calc R . .
H5B H 0.0382 0.5806 0.6142 0.117 Uiso 1 1 calc R . .
H5C H 0.2501 0.5574 0.6132 0.117 Uiso 1 1 calc R . .
C6 C 0.2522(5) 0.0064(5) 1.0037(3) 0.0512(6) Uani 1 1 d . . .
C7 C 0.2502(6) -0.1634(5) 0.9732(3) 0.0571(7) Uani 1 1 d . . .
H7 H 0.2343 -0.1859 0.8934 0.068 Uiso 1 1 calc R . .
C8 C 0.2713(6) -0.2967(5) 1.0583(3) 0.0583(7) Uani 1 1 d . . .
H8 H 0.2673 -0.4097 1.0378 0.070 Uiso 1 1 calc R . .
C9 C 0.2985(5) -0.2655(5) 1.1752(3) 0.0545(7) Uani 1 1 d . . .
C10 C 0.3014(6) -0.0995(6) 1.2064(3) 0.0616(8) Uani 1 1 d . . .
H10 H 0.3188 -0.0787 1.2861 0.074 Uiso 1 1 calc R . .
C11 C 0.2787(6) 0.0365(6) 1.1210(3) 0.0624(8) Uani 1 1 d . . .
H11 H 0.2813 0.1500 1.1424 0.075 Uiso 1 1 calc 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
I1 0.0704(2) 0.0872(3) 0.0620(2) 0.03980(15) -0.01725(13) -0.03298(17)
O1 0.111(3) 0.101(2) 0.0490(14) 0.0321(15) -0.0122(15) -0.051(2)
O2 0.165(4) 0.082(2) 0.0620(18) 0.0203(15) -0.036(2) -0.074(3)
N1 0.0534(14) 0.0593(14) 0.0390(11) 0.0179(10) -0.0112(9) -0.0281(12)
N2 0.0688(17) 0.0600(15) 0.0415(11) 0.0159(10) -0.0147(11) -0.0340(14)
C1 0.121(4) 0.092(3) 0.051(2) 0.012(2) -0.013(2) -0.061(3)
C2 0.0640(18) 0.0636(18) 0.0401(13) 0.0165(12) -0.0107(12) -0.0294(16)
C3 0.0556(16) 0.0633(18) 0.0429(13) 0.0189(12) -0.0141(12) -0.0302(14)
C4 0.080(2) 0.071(2) 0.0585(19) 0.0232(16) -0.0193(17) -0.048(2)
C5 0.106(4) 0.079(3) 0.070(2) 0.037(2) -0.025(2) -0.059(3)
C6 0.0544(16) 0.0607(17) 0.0386(12) 0.0147(12) -0.0100(11) -0.0274(14)
C7 0.071(2) 0.0581(17) 0.0395(13) 0.0111(12) -0.0134(13) -0.0277(16)
C8 0.068(2) 0.0587(18) 0.0434(14) 0.0148(13) -0.0132(13) -0.0252(16)
C9 0.0495(15) 0.0701(19) 0.0362(12) 0.0186(12) -0.0081(10) -0.0226(14)
C10 0.071(2) 0.080(2) 0.0361(13) 0.0157(14) -0.0123(13) -0.0378(19)
C11 0.081(2) 0.075(2) 0.0389(13) 0.0147(14) -0.0161(14) -0.042(2)

_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
I1 C9 2.094(3) . ?
O1 C2 1.230(4) . ?
O2 C4 1.233(5) . ?
N1 N2 1.299(4) . ?
N1 C3 1.319(4) . ?
N2 C6 1.382(4) . ?
N2 H2 0.8800 . ?
C1 C2 1.498(6) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C3 1.494(5) . ?
C3 C4 1.462(6) . ?
C4 C5 1.506(6) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C11 1.400(4) . ?
C6 C7 1.410(5) . ?
C7 C8 1.376(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.400(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.386(6) . ?
C10 C11 1.392(5) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?

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
N2 N1 C3 121.5(3) . . ?
N1 N2 C6 120.4(3) . . ?
N1 N2 H2 119.8 . . ?
C6 N2 H2 119.8 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C3 121.1(4) . . ?
O1 C2 C1 119.9(3) . . ?
C3 C2 C1 119.0(3) . . ?
N1 C3 C4 124.2(3) . . ?
N1 C3 C2 112.3(3) . . ?
C4 C3 C2 123.5(3) . . ?
O2 C4 C3 118.7(4) . . ?
O2 C4 C5 118.8(4) . . ?
C3 C4 C5 122.4(4) . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N2 C6 C11 118.7(3) . . ?
N2 C6 C7 122.0(3) . . ?
C11 C6 C7 119.3(3) . . ?
C8 C7 C6 120.4(3) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C9 119.9(3) . . ?
C7 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C10 C9 C8 120.4(3) . . ?
C10 C9 I1 120.5(2) . . ?
C8 C9 I1 119.1(3) . . ?
C9 C10 C11 120.0(3) . . ?
C9 C10 H10 120.0 . . ?
C11 C10 H10 120.0 . . ?
C10 C11 C6 120.1(4) . . ?
C10 C11 H11 120.0 . . ?
C6 C11 H11 120.0 . . ?

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
C3 N1 N2 C6 -179.1(3) . . . . ?
N2 N1 C3 C4 -4.0(5) . . . . ?
N2 N1 C3 C2 176.5(3) . . . . ?
O1 C2 C3 N1 -164.1(4) . . . . ?
C1 C2 C3 N1 16.6(5) . . . . ?
O1 C2 C3 C4 16.3(6) . . . . ?
C1 C2 C3 C4 -163.0(4) . . . . ?
N1 C3 C4 O2 0.7(7) . . . . ?
C2 C3 C4 O2 -179.8(4) . . . . ?
N1 C3 C4 C5 -175.7(4) . . . . ?
C2 C3 C4 C5 3.8(7) . . . . ?
N1 N2 C6 C11 168.0(3) . . . . ?
N1 N2 C6 C7 -13.0(5) . . . . ?
N2 C6 C7 C8 -178.0(3) . . . . ?
C11 C6 C7 C8 1.0(6) . . . . ?
C6 C7 C8 C9 -1.2(6) . . . . ?
C7 C8 C9 C10 1.0(6) . . . . ?
C7 C8 C9 I1 178.2(3) . . . . ?
C8 C9 C10 C11 -0.5(6) . . . . ?
I1 C9 C10 C11 -177.7(3) . . . . ?
C9 C10 C11 C6 0.3(6) . . . . ?
N2 C6 C11 C10 178.6(3) . . . . ?
C7 C6 C11 C10 -0.5(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        34.84
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         2.042
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.120

# TEXT

_publ_section_abstract           
; Three new hydrazone compounds having a p-iodoaryl and
diketohydrazone molecular skeleton in common but feature a
gradual replacement of the two methyl for trifluoromethyl
terminal groups were prepared and comparatively studied with
regard to their crystal structures. A quantum chemical calculation
of the single trifluoromethyl modified compound was undertaken to
decide on to low energy conformation referring to the hydrogen
bonded ring site. While the molecular structures of the compounds
remain rather unimpaired by the fluorine substitution, their
crystalline packings are markedly affected, showing a distinct
supramolecular control in the crystal lattices.
;

# Attachment '3.cif'

data_jama40c
_database_code_depnum_ccdc_archive 'CCDC 661393'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C44 H20 F24 I4 N8 O8'
_chemical_formula_weight         1752.28

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'P -4 2(1) c'
_symmetry_space_group_name_Hall  'P -4 2n'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'
'-x+1/2, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-y+1/2, -x+1/2, z+1/2'
'y+1/2, x+1/2, z+1/2'

_cell_length_a                   19.9387(6)
_cell_length_b                   19.9387(6)
_cell_length_c                   6.7572(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2686.34(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       column
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.166
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1664
_exptl_absorpt_coefficient_mu    2.464
_exptl_absorpt_correction_type   'multi scan'
_exptl_absorpt_correction_T_min  0.4160
_exptl_absorpt_correction_T_max  0.7080
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'

_exptl_special_details           
;
?
;

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        none
_diffrn_reflns_number            109881
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.44
_diffrn_reflns_theta_max         35.54
_reflns_number_total             6149
_reflns_number_gt                5201
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART APEX2 (Bruker-AXS)'
_computing_cell_refinement       'SAINT-NT (Bruker, 2003)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL

_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^)+(0.0643P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.005(16)
_refine_ls_number_reflns         6149
_refine_ls_number_parameters     203
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0463
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.1057
_refine_ls_wR_factor_gt          0.0980
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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
I1 I 0.997579(9) 0.397577(9) -0.01159(3) 0.02995(6) Uani 1 1 d . . .
F1 F 0.83719(8) 0.78621(8) 1.2951(3) 0.0269(3) Uani 1 1 d . . .
F2 F 0.83055(8) 0.71691(7) 1.0525(3) 0.0320(4) Uani 1 1 d . . .
F3 F 0.74541(8) 0.77810(8) 1.1242(3) 0.0279(3) Uani 1 1 d . . .
F4 F 0.95318(8) 0.91721(9) 0.7818(2) 0.0288(3) Uani 1 1 d . . .
F5 F 0.87470(9) 0.91574(11) 0.5610(2) 0.0397(4) Uani 1 1 d . . .
F6 F 0.91790(9) 1.00945(10) 0.6544(3) 0.0445(5) Uani 1 1 d . . .
O1 O 0.86840(11) 0.81042(11) 0.8193(3) 0.0322(4) Uani 1 1 d . . .
O2 O 0.82397(10) 1.01396(9) 0.9078(3) 0.0251(4) Uani 1 1 d . . .
N1 N 0.78951(10) 0.91021(10) 1.1719(3) 0.0181(4) Uani 1 1 d . . .
N2 N 0.77067(10) 0.96831(10) 1.2344(3) 0.0199(4) Uani 1 1 d . . .
H2 H 0.7777(15) 1.0018(14) 1.159(3) 0.015(6) Uiso 1 1 d . . .
C1 C 0.81279(13) 0.77762(13) 1.1127(4) 0.0219(4) Uani 1 1 d . . .
C2 C 0.83847(12) 0.83088(13) 0.9625(4) 0.0212(5) Uani 1 1 d . . .
C3 C 0.82456(11) 0.90140(11) 1.0068(4) 0.0188(4) Uani 1 1 d . . .
C4 C 0.84552(12) 0.95757(13) 0.8819(3) 0.0216(4) Uani 1 1 d . . .
C5 C 0.89864(13) 0.94876(15) 0.7155(4) 0.0271(5) Uani 1 1 d . . .
C6 C 0.97330(12) 0.26509(11) 0.5850(4) 0.0183(4) Uani 1 1 d . . .
C7 C 0.91657(11) 0.27933(11) 0.4728(4) 0.0198(4) Uani 1 1 d . . .
H7 H 0.8737 0.2635 0.5130 0.024 Uiso 1 1 calc R . .
C8 C 0.92346(12) 0.31716(12) 0.3005(4) 0.0208(4) Uani 1 1 d . . .
H8 H 0.8852 0.3280 0.2229 0.025 Uiso 1 1 calc R . .
C9 C 0.98691(11) 0.33880(11) 0.2433(4) 0.0200(4) Uani 1 1 d . . .
C10 C 1.04373(12) 0.32345(12) 0.3538(4) 0.0219(5) Uani 1 1 d . . .
H10 H 1.0867 0.3382 0.3115 0.026 Uiso 1 1 calc R . .
C11 C 1.03699(11) 0.28612(12) 0.5274(4) 0.0217(4) Uani 1 1 d . . .
H11 H 1.0752 0.2752 0.6049 0.026 Uiso 1 1 calc 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
I1 0.02854(9) 0.02524(8) 0.03607(10) 0.01587(6) 0.00473(10) 0.00111(6)
F1 0.0297(8) 0.0272(8) 0.0239(7) -0.0003(6) -0.0021(6) 0.0042(6)
F2 0.0362(8) 0.0192(7) 0.0406(9) -0.0065(6) -0.0005(7) 0.0060(6)
F3 0.0169(7) 0.0244(7) 0.0423(9) -0.0017(7) 0.0039(6) -0.0038(6)
F4 0.0156(7) 0.0371(9) 0.0338(8) 0.0081(7) -0.0003(6) 0.0014(6)
F5 0.0250(8) 0.0731(13) 0.0210(8) -0.0034(8) 0.0011(6) 0.0093(8)
F6 0.0388(10) 0.0442(11) 0.0506(10) 0.0293(9) 0.0177(8) 0.0038(8)
O1 0.0334(10) 0.0340(10) 0.0293(10) -0.0117(8) 0.0123(8) -0.0031(9)
O2 0.0325(10) 0.0199(8) 0.0231(8) 0.0013(6) 0.0015(7) -0.0032(7)
N1 0.0181(9) 0.0177(8) 0.0184(9) -0.0018(7) 0.0016(7) -0.0002(7)
N2 0.0230(9) 0.0150(8) 0.0217(9) 0.0014(7) 0.0022(7) 0.0001(7)
C1 0.0209(11) 0.0200(11) 0.0247(11) -0.0031(9) 0.0002(9) 0.0035(9)
C2 0.0139(9) 0.0268(11) 0.0229(13) -0.0054(9) 0.0019(8) -0.0008(9)
C3 0.0176(9) 0.0213(9) 0.0175(9) -0.0026(8) 0.0017(8) -0.0017(7)
C4 0.0190(10) 0.0285(12) 0.0173(10) 0.0025(8) -0.0019(8) -0.0015(9)
C5 0.0177(11) 0.0392(14) 0.0244(11) 0.0110(10) 0.0035(9) 0.0006(10)
C6 0.0186(9) 0.0160(9) 0.0202(10) 0.0034(7) 0.0005(8) 0.0000(8)
C7 0.0181(9) 0.0164(9) 0.0249(11) 0.0019(8) 0.0025(8) 0.0001(7)
C8 0.0181(10) 0.0186(10) 0.0257(11) 0.0041(8) 0.0001(8) 0.0009(8)
C9 0.0211(11) 0.0146(9) 0.0242(10) 0.0046(8) 0.0040(8) 0.0018(7)
C10 0.0203(11) 0.0177(10) 0.0276(12) 0.0025(9) 0.0039(9) -0.0011(9)
C11 0.0162(9) 0.0251(10) 0.0238(11) 0.0047(9) 0.0003(8) -0.0002(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
I1 C9 2.094(2) . ?
F1 C1 1.336(3) . ?
F2 C1 1.325(3) . ?
F3 C1 1.346(3) . ?
F4 C5 1.334(3) . ?
F5 C5 1.324(3) . ?
F6 C5 1.335(3) . ?
O1 C2 1.208(3) . ?
O2 C4 1.216(3) . ?
N1 N2 1.289(3) . ?
N1 C3 1.328(3) . ?
N2 C6 1.417(3) 4_657 ?
N2 H2 0.85(3) . ?
C1 C2 1.556(4) . ?
C2 C3 1.464(3) . ?
C3 C4 1.463(3) . ?
C4 C5 1.554(4) . ?
C6 C7 1.391(3) . ?
C6 C11 1.393(3) . ?
C6 N2 1.417(3) 3_567 ?
C10 C11 1.395(3) . ?
C11 H11 0.9500 . ?
C9 C10 1.391(3) . ?
C10 H10 0.9500 . ?
C8 C9 1.391(3) . ?
C7 C8 1.394(3) . ?
C8 H8 0.9500 . ?
C7 H7 0.9500 . ?

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
N2 N1 C3 123.2(2) . . ?
N1 N2 C6 119.47(19) . 4_657 ?
N1 N2 H2 117.5(18) . . ?
C6 N2 H2 122.8(18) 4_657 . ?
F2 C1 F1 107.6(2) . . ?
F2 C1 F3 106.9(2) . . ?
F1 C1 F3 108.0(2) . . ?
F2 C1 C2 109.6(2) . . ?
F1 C1 C2 113.2(2) . . ?
F3 C1 C2 111.2(2) . . ?
O1 C2 C3 125.6(3) . . ?
O1 C2 C1 117.1(2) . . ?
C3 C2 C1 117.37(19) . . ?
N1 C3 C4 122.2(2) . . ?
N1 C3 C2 113.5(2) . . ?
C4 C3 C2 124.3(2) . . ?
O2 C4 C3 121.6(2) . . ?
O2 C4 C5 116.7(2) . . ?
C3 C4 C5 121.7(2) . . ?
F5 C5 F4 108.9(2) . . ?
F5 C5 F6 108.1(2) . . ?
F4 C5 F6 107.3(2) . . ?
F5 C5 C4 112.4(2) . . ?
F4 C5 C4 111.5(2) . . ?
F6 C5 C4 108.5(2) . . ?
C7 C6 C11 121.8(2) . . ?
C7 C6 N2 121.0(2) . 3_567 ?
C11 C6 N2 117.2(2) . 3_567 ?
C6 C11 C10 118.9(2) . . ?
C6 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C9 C10 C11 119.3(2) . . ?
C9 C10 H10 120.3 . . ?
C11 C10 H10 120.3 . . ?
C8 C9 C10 121.6(2) . . ?
C10 C9 I1 118.81(17) . . ?
C8 C9 I1 119.62(17) . . ?
C7 C8 C9 119.3(2) . . ?
C9 C8 H8 120.4 . . ?
C7 C8 H8 120.4 . . ?
C6 C7 C8 119.1(2) . . ?
C6 C7 H7 120.5 . . ?
C8 C7 H7 120.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 N2 C6 -178.4(2) . . . 4_657 ?
F2 C1 C2 O1 0.9(3) . . . . ?
F1 C1 C2 O1 121.1(3) . . . . ?
F3 C1 C2 O1 -117.0(3) . . . . ?
F2 C1 C2 C3 -178.9(2) . . . . ?
F1 C1 C2 C3 -58.7(3) . . . . ?
F3 C1 C2 C3 63.2(3) . . . . ?
N2 N1 C3 C4 0.7(3) . . . . ?
N2 N1 C3 C2 -178.3(2) . . . . ?
O1 C2 C3 N1 178.7(2) . . . . ?
C1 C2 C3 N1 -1.5(3) . . . . ?
O1 C2 C3 C4 -0.2(4) . . . . ?
C1 C2 C3 C4 179.6(2) . . . . ?
N1 C3 C4 O2 -10.5(4) . . . . ?
C2 C3 C4 O2 168.3(2) . . . . ?
N1 C3 C4 C5 166.8(2) . . . . ?
C2 C3 C4 C5 -14.4(3) . . . . ?
O2 C4 C5 F5 -109.4(3) . . . . ?
C3 C4 C5 F5 73.1(3) . . . . ?
O2 C4 C5 F4 127.9(3) . . . . ?
C3 C4 C5 F4 -49.5(3) . . . . ?
O2 C4 C5 F6 10.0(3) . . . . ?
C3 C4 C5 F6 -167.4(2) . . . . ?
C7 C6 C11 C10 1.1(4) . . . . ?
N2 C6 C11 C10 -177.9(2) 3_567 . . . ?
C6 C11 C10 C9 0.1(4) . . . . ?
C8 C9 C10 C11 -0.8(4) . . . . ?
C11 C10 C9 I1 177.98(18) . . . . ?
C7 C8 C9 C10 0.2(4) . . . . ?
I1 C9 C8 C7 -178.56(17) . . . . ?
C11 C6 C7 C8 -1.7(4) . . . . ?
N2 C6 C7 C8 177.2(2) 3_567 . . . ?
C6 C7 C8 C9 1.0(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        35.54
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         2.050
_refine_diff_density_min         -1.490
_refine_diff_density_rms         0.151


