# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_120905b_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H9 F2 I N'
_chemical_formula_weight         380.14

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'
N N 0.0061 0.0033 '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   P2(1)/c

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                   9.5953(7)
_cell_length_b                   5.7426(4)
_cell_length_c                   24.9356(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.9550(10)
_cell_angle_gamma                90.00
_cell_volume                     1366.59(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2076
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      23.65

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.848
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             732
_exptl_absorpt_coefficient_mu    2.354
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7191
_exptl_absorpt_correction_T_max  0.7987
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_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  '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_%        ?
_diffrn_reflns_number            7761
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0380
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.64
_diffrn_reflns_theta_max         27.65
_reflns_number_total             3151
_reflns_number_gt                2458
_reflns_threshold_expression     >2sigma(I)

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

_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     
'calc w=1/[σ²(Fo²)+(0.0273P)²+0.0000P] where P=(Fo²+2Fc²)/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         3151
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0313
_refine_ls_wR_factor_ref         0.0663
_refine_ls_wR_factor_gt          0.0619
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_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 0.19401(2) -0.09780(4) 0.432667(9) 0.04716(9) Uani 1 1 d . . .
C1 C 0.0780(3) -0.3367(5) 0.47325(12) 0.0381(7) Uani 1 1 d . . .
C2 C -0.0033(3) -0.5036(6) 0.44541(12) 0.0419(7) Uani 1 1 d . . .
C3 C -0.0789(3) -0.6627(5) 0.47158(13) 0.0404(7) Uani 1 1 d . . .
C4 C 0.4084(3) 0.4045(6) 0.37339(13) 0.0420(7) Uani 1 1 d . . .
C5 C 0.4929(4) 0.3981(7) 0.42240(15) 0.0566(9) Uani 1 1 d . . .
H5 H 0.4828 0.2770 0.4464 0.068 Uiso 1 1 calc R . .
C6 C 0.5899(4) 0.5670(8) 0.43535(16) 0.0638(11) Uani 1 1 d . . .
H6 H 0.6447 0.5626 0.4684 0.077 Uiso 1 1 calc R . .
C7 C 0.6069(4) 0.7463(7) 0.39918(17) 0.0674(11) Uani 1 1 d . . .
H7 H 0.6733 0.8616 0.4081 0.081 Uiso 1 1 calc R . .
C8 C 0.5268(4) 0.7545(6) 0.35065(15) 0.0549(9) Uani 1 1 d . . .
H8 H 0.5403 0.8747 0.3267 0.066 Uiso 1 1 calc R . .
C9 C 0.4248(3) 0.5857(5) 0.33620(13) 0.0424(8) Uani 1 1 d . . .
C10 C 0.3350(3) 0.5864(5) 0.28606(13) 0.0410(7) Uani 1 1 d . . .
C11 C 0.3400(4) 0.7542(6) 0.24491(14) 0.0522(9) Uani 1 1 d . . .
H11 H 0.4038 0.8762 0.2497 0.063 Uiso 1 1 calc R . .
C12 C 0.2536(4) 0.7405(7) 0.19870(15) 0.0649(11) Uani 1 1 d . . .
H12 H 0.2594 0.8534 0.1723 0.078 Uiso 1 1 calc R . .
C13 C 0.1561(4) 0.5613(7) 0.18961(16) 0.0625(11) Uani 1 1 d . . .
H13 H 0.0968 0.5551 0.1577 0.075 Uiso 1 1 calc R . .
C14 C 0.1488(4) 0.3950(7) 0.22835(14) 0.0563(9) Uani 1 1 d . . .
H14 H 0.0847 0.2738 0.2226 0.068 Uiso 1 1 calc R . .
C15 C 0.2374(3) 0.4051(6) 0.27699(13) 0.0444(8) Uani 1 1 d . . .
C16 C 0.2317(4) 0.2337(6) 0.31774(14) 0.0518(9) Uani 1 1 d . . .
H16 H 0.1668 0.1141 0.3111 0.062 Uiso 1 1 calc R . .
F1 F -0.0101(2) -0.5133(4) 0.39131(7) 0.0662(6) Uani 1 1 d . . .
F2 F -0.1553(2) -0.8227(4) 0.44199(8) 0.0611(6) Uani 1 1 d . . .
N1 N 0.3093(3) 0.2302(5) 0.36319(11) 0.0486(7) Uani 1 1 d . . .


_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 C1 2.093(3) . ?
I1 N1 2.858(3) . ?
I1 C16 3.490(3) . ?
C1 C3 1.375(4) 3_546 ?
C1 C2 1.377(4) . ?
C2 F1 1.345(3) . ?
C2 C3 1.373(4) . ?
C3 F2 1.347(3) . ?
C3 C1 1.375(4) 3_546 ?
C4 N1 1.386(4) . ?
C4 C5 1.395(5) . ?
C4 C9 1.413(4) . ?
C5 C6 1.359(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.390(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.365(5) . ?
C7 H7 0.9300 . ?
C8 C9 1.398(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.443(5) . ?
C10 C15 1.403(4) . ?
C10 C11 1.412(4) . ?
C11 C12 1.350(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.394(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.365(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.408(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.420(4) . ?
C16 N1 1.290(4) . ?
C16 H16 0.9300 . ?
F2 H7 2.5331 1_435 ?

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
C1 I1 N1 169.68(11) . . ?
C1 I1 C16 149.35(11) . . ?
N1 I1 C16 20.51(8) . . ?
C3 C1 C2 116.6(3) 3_546 . ?
C3 C1 I1 122.5(2) 3_546 . ?
C2 C1 I1 120.9(2) . . ?
F1 C2 C3 118.4(3) . . ?
F1 C2 C1 120.0(3) . . ?
C3 C2 C1 121.5(3) . . ?
F2 C3 C2 118.6(3) . . ?
F2 C3 C1 119.5(3) . 3_546 ?
C2 C3 C1 121.9(3) . 3_546 ?
N1 C4 C5 117.8(3) . . ?
N1 C4 C9 122.1(3) . . ?
C5 C4 C9 120.0(3) . . ?
C6 C5 C4 120.7(4) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 119.9(4) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C6 120.5(4) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C9 121.3(4) . . ?
C7 C8 H8 119.4 . . ?
C9 C8 H8 119.4 . . ?
C8 C9 C4 117.6(3) . . ?
C8 C9 C10 124.1(3) . . ?
C4 C9 C10 118.3(3) . . ?
C15 C10 C11 117.5(3) . . ?
C15 C10 C9 117.8(3) . . ?
C11 C10 C9 124.7(3) . . ?
C12 C11 C10 121.1(3) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C11 C12 C13 121.6(3) . . ?
C11 C12 H12 119.2 . . ?
C13 C12 H12 119.2 . . ?
C14 C13 C12 118.9(4) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
C13 C14 C15 120.7(4) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?
C10 C15 C14 120.2(3) . . ?
C10 C15 C16 118.3(3) . . ?
C14 C15 C16 121.6(3) . . ?
N1 C16 C15 125.3(3) . . ?
N1 C16 I1 50.93(17) . . ?
C15 C16 I1 168.7(2) . . ?
N1 C16 H16 117.3 . . ?
C15 C16 H16 117.3 . . ?
I1 C16 H16 67.6 . . ?
C3 F2 H7 165.6 . 1_435 ?
C16 N1 C4 118.2(3) . . ?
C16 N1 I1 108.6(2) . . ?
C4 N1 I1 131.8(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C7 H7 F2 0.93 2.53 3.459(4) 174.0 1_675

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        27.65
_diffrn_measured_fraction_theta_full 0.983
_refine_diff_density_max         0.594
_refine_diff_density_min         -0.393
_refine_diff_density_rms         0.076
_database_code_depnum_ccdc_archive 'CCDC 975980'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_120503e_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H9 F4 I2 N'
_chemical_formula_weight         581.07

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'
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   P2(1)

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

_cell_length_a                   8.3207(7)
_cell_length_b                   6.7511(6)
_cell_length_c                   32.383(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.561(2)
_cell_angle_gamma                90.00
_cell_volume                     1807.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3114
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      23.48

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.136
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1088
_exptl_absorpt_coefficient_mu    3.521
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6027
_exptl_absorpt_correction_T_max  0.7906
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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_%        ?
_diffrn_reflns_number            8914
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0491
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       38
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         25.24
_reflns_number_total             5333
_reflns_number_gt                4661
_reflns_threshold_expression     >2sigma(I)

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

_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     
'calc w=1/[σ²(Fo²)+(0.0245P)²+2.8295P] where P=(Fo²+2Fc²)/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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_number_reflns         5333
_refine_ls_number_parameters     469
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0488
_refine_ls_R_factor_gt           0.0406
_refine_ls_wR_factor_ref         0.0826
_refine_ls_wR_factor_gt          0.0791
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_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 0.4295(9) 0.8423(15) 0.5901(2) 0.0397(19) Uani 1 1 d . . .
C2 C 0.5002(12) 0.6549(16) 0.5869(3) 0.051(2) Uani 1 1 d . . .
C3 C 0.5887(12) 0.5656(14) 0.6205(3) 0.048(2) Uani 1 1 d . . .
C4 C 0.6099(11) 0.6584(15) 0.6585(3) 0.048(2) Uani 1 1 d . . .
C5 C 0.5439(10) 0.8426(16) 0.6618(2) 0.047(2) Uani 1 1 d . . .
C6 C 0.4592(9) 0.9251(12) 0.6282(3) 0.038(2) Uani 1 1 d . . .
C7 C 0.9824(10) 0.1686(14) 0.8392(3) 0.044(2) Uani 1 1 d . . .
C8 C 0.9157(10) -0.0161(16) 0.8348(3) 0.051(2) Uani 1 1 d . . .
C9 C 0.8548(10) -0.1087(13) 0.8674(3) 0.045(2) Uani 1 1 d . . .
C10 C 0.8612(9) -0.0192(15) 0.9056(2) 0.043(2) Uani 1 1 d . . .
C11 C 0.9334(11) 0.1679(14) 0.9098(3) 0.047(2) Uani 1 1 d . . .
C12 C 0.9909(11) 0.2556(13) 0.8773(3) 0.043(2) Uani 1 1 d . . .
C13 C 0.3742(10) 0.1385(13) 0.9368(3) 0.039(2) Uani 1 1 d . . .
C14 C 0.4508(9) 0.3264(14) 0.9310(3) 0.047(2) Uani 1 1 d . . .
H14 H 0.4621 0.4173 0.9527 0.056 Uiso 1 1 calc R . .
C15 C 0.5058(11) 0.3727(14) 0.8951(3) 0.052(2) Uani 1 1 d . . .
H15 H 0.5533 0.4961 0.8926 0.062 Uiso 1 1 calc R . .
C16 C 0.4949(10) 0.2418(13) 0.8606(3) 0.044(2) Uani 1 1 d . . .
C17 C 0.5565(11) 0.2852(16) 0.8239(3) 0.051(2) Uani 1 1 d . . .
H17 H 0.6066 0.4072 0.8215 0.061 Uiso 1 1 calc R . .
C18 C 0.5477(12) 0.1598(19) 0.7914(3) 0.064(3) Uani 1 1 d . . .
H18 H 0.5838 0.1989 0.7665 0.076 Uiso 1 1 calc R . .
C19 C 0.4847(14) -0.027(2) 0.7954(3) 0.077(3) Uani 1 1 d . . .
H19 H 0.4881 -0.1192 0.7741 0.092 Uiso 1 1 calc R . .
C20 C 0.4172(11) -0.0780(15) 0.8304(3) 0.054(2) Uani 1 1 d . . .
H20 H 0.3676 -0.2009 0.8317 0.065 Uiso 1 1 calc R . .
C21 C 0.4213(10) 0.0523(14) 0.8644(2) 0.040(2) Uani 1 1 d . . .
C22 C 0.3594(9) 0.0032(13) 0.9031(2) 0.0360(18) Uani 1 1 d . . .
C23 C 0.2845(9) -0.1828(15) 0.9102(3) 0.043(2) Uani 1 1 d . . .
H23 H 0.2710 -0.2783 0.8894 0.052 Uiso 1 1 calc R . .
C24 C 0.2340(11) -0.2165(15) 0.9475(3) 0.052(3) Uani 1 1 d . . .
H24 H 0.1863 -0.3371 0.9527 0.063 Uiso 1 1 calc R . .
C25 C 0.2527(12) -0.0715(18) 0.9784(3) 0.060(3) Uani 1 1 d . . .
H25 H 0.2149 -0.0982 1.0038 0.072 Uiso 1 1 calc R . .
C26 C -0.0620(10) 0.6813(13) 0.5681(3) 0.040(2) Uani 1 1 d . . .
C27 C 0.0171(10) 0.4967(15) 0.5714(3) 0.052(2) Uani 1 1 d . . .
H27 H 0.0080 0.4114 0.5487 0.062 Uiso 1 1 calc R . .
C28 C 0.1058(11) 0.4419(16) 0.6070(3) 0.057(3) Uani 1 1 d . . .
H28 H 0.1569 0.3192 0.6085 0.069 Uiso 1 1 calc R . .
C29 C 0.1230(10) 0.5699(14) 0.6430(3) 0.046(2) Uani 1 1 d . . .
C30 C 0.2153(11) 0.5089(17) 0.6796(3) 0.056(2) Uani 1 1 d . . .
H30 H 0.2661 0.3860 0.6810 0.067 Uiso 1 1 calc R . .
C31 C 0.2298(13) 0.632(2) 0.7132(3) 0.067(3) Uani 1 1 d . . .
H31 H 0.2893 0.5910 0.7378 0.080 Uiso 1 1 calc R . .
C32 C 0.1556(13) 0.819(2) 0.7111(3) 0.064(3) Uani 1 1 d . . .
H32 H 0.1670 0.9030 0.7340 0.077 Uiso 1 1 calc R . .
C33 C 0.0673(11) 0.8781(15) 0.6752(3) 0.051(2) Uani 1 1 d . . .
H33 H 0.0208 1.0035 0.6739 0.062 Uiso 1 1 calc R . .
C34 C 0.0444(10) 0.7556(14) 0.6404(3) 0.044(2) Uani 1 1 d . . .
C35 C -0.0474(9) 0.8105(14) 0.6021(2) 0.0407(19) Uani 1 1 d . . .
C36 C -0.1316(10) 0.9932(15) 0.5962(3) 0.047(2) Uani 1 1 d . . .
H36 H -0.1302 1.0831 0.6180 0.056 Uiso 1 1 calc R . .
C37 C -0.2153(12) 1.0372(16) 0.5580(3) 0.061(3) Uani 1 1 d . . .
H37 H -0.2663 1.1590 0.5533 0.073 Uiso 1 1 calc R . .
C38 C -0.2218(12) 0.8969(16) 0.5270(3) 0.055(3) Uani 1 1 d . . .
H38 H -0.2824 0.9255 0.5018 0.066 Uiso 1 1 calc R . .
F1 F 0.4830(8) 0.5576(9) 0.55066(17) 0.0758(19) Uani 1 1 d . . .
F2 F 0.6520(8) 0.3883(9) 0.6156(2) 0.0807(19) Uani 1 1 d . . .
F3 F 0.5629(7) 0.9401(10) 0.69801(16) 0.0747(18) Uani 1 1 d . . .
F4 F 0.3913(7) 1.1102(8) 0.63385(17) 0.0618(15) Uani 1 1 d . . .
F5 F 0.9046(8) -0.1091(9) 0.79807(16) 0.0761(18) Uani 1 1 d . . .
F6 F 0.7869(8) -0.2867(9) 0.86120(18) 0.0691(17) Uani 1 1 d . . .
F7 F 0.9448(7) 0.2582(9) 0.94650(17) 0.0726(18) Uani 1 1 d . . .
F8 F 1.0597(7) 0.4357(8) 0.88312(19) 0.0717(17) Uani 1 1 d . . .
I1 I 0.29954(7) 0.97914(10) 0.539180(18) 0.05449(18) Uani 1 1 d . . .
I2 I 0.74160(8) 0.52248(12) 0.70927(2) 0.0781(3) Uani 1 1 d . . .
I3 I 1.06670(8) 0.31654(12) 0.78907(2) 0.0700(2) Uani 1 1 d . . .
I4 I 0.77166(7) -0.15851(10) 0.956459(18) 0.05380(17) Uani 1 1 d . . .
N1 N 0.3204(10) 0.0984(13) 0.9735(2) 0.051(2) Uani 1 1 d . . .
N2 N -0.1471(10) 0.7242(13) 0.5310(2) 0.051(2) Uani 1 1 d . . .


_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 C6 1.351(11) . ?
C1 C2 1.404(13) . ?
C1 I1 2.083(8) . ?
C1 C37 3.500(13) 1_655 ?
C2 F1 1.339(10) . ?
C2 C3 1.380(13) . ?
C2 C38 3.579(14) 1_655 ?
C3 F2 1.325(10) . ?
C3 C4 1.374(13) . ?
C3 C35 3.559(12) 1_655 ?
C4 C5 1.369(14) . ?
C4 I2 2.081(9) . ?
C5 F3 1.337(9) . ?
C5 C6 1.348(11) . ?
C6 F4 1.392(9) . ?
C7 C12 1.359(12) . ?
C7 C8 1.366(14) . ?
C7 I3 2.094(9) . ?
C8 F5 1.340(10) . ?
C8 C9 1.370(12) . ?
C9 F6 1.333(10) . ?
C9 C10 1.372(12) . ?
C10 C11 1.399(14) . ?
C10 I4 2.106(8) . ?
C10 C24 3.504(12) 1_655 ?
C11 F7 1.329(10) . ?
C11 C12 1.344(13) . ?
C12 F8 1.348(10) . ?
C12 C22 3.524(11) 1_655 ?
C13 N1 1.343(11) . ?
C13 C22 1.419(12) . ?
C13 C14 1.442(13) . ?
C14 C15 1.333(12) . ?
C14 H14 0.9300 . ?
C15 C16 1.419(12) . ?
C15 H15 0.9300 . ?
C16 C17 1.378(12) . ?
C16 C21 1.430(12) . ?
C17 C18 1.348(14) . ?
C17 H17 0.9300 . ?
C18 C19 1.379(17) . ?
C18 H18 0.9300 . ?
C19 C20 1.364(14) . ?
C19 H19 0.9300 . ?
C20 C21 1.408(12) . ?
C20 H20 0.9300 . ?
C21 C22 1.445(11) . ?
C22 C23 1.432(12) . ?
C23 C24 1.343(11) . ?
C23 H23 0.9300 . ?
C24 C25 1.397(14) . ?
C24 H24 0.9300 . ?
C25 N1 1.296(13) . ?
C25 H25 0.9300 . ?
C26 N2 1.355(11) . ?
C26 C35 1.398(11) . ?
C26 C27 1.408(13) . ?
C27 C28 1.348(12) . ?
C27 H27 0.9300 . ?
C28 C29 1.445(13) . ?
C28 H28 0.9300 . ?
C29 C30 1.398(12) . ?
C29 C34 1.412(13) . ?
C30 C31 1.362(15) . ?
C30 H30 0.9300 . ?
C31 C32 1.409(17) . ?
C31 H31 0.9300 . ?
C32 C33 1.360(13) . ?
C32 H32 0.9300 . ?
C33 C34 1.393(12) . ?
C33 H33 0.9300 . ?
C34 C35 1.431(11) . ?
C35 C36 1.421(12) . ?
C36 C37 1.379(13) . ?
C36 H36 0.9300 . ?
C37 C38 1.377(14) . ?
C37 H37 0.9300 . ?
C38 N2 1.321(12) . ?
C38 H38 0.9300 . ?
I1 N2 2.975(8) 2_556 ?
I2 I3 3.7858(9) . ?
I3 C31 3.628(11) 1_655 ?
I4 N1 2.971(8) 2_647 ?

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
C6 C1 C2 114.0(8) . . ?
C6 C1 I1 124.3(7) . . ?
C2 C1 I1 121.6(6) . . ?
C6 C1 C37 92.5(5) . 1_655 ?
C2 C1 C37 86.7(5) . 1_655 ?
I1 C1 C37 88.7(3) . 1_655 ?
F1 C2 C3 118.1(9) . . ?
F1 C2 C1 120.3(8) . . ?
C3 C2 C1 121.7(8) . . ?
F1 C2 C38 76.1(5) . 1_655 ?
C3 C2 C38 107.9(6) . 1_655 ?
C1 C2 C38 86.0(5) . 1_655 ?
F2 C3 C4 120.4(9) . . ?
F2 C3 C2 119.0(9) . . ?
C4 C3 C2 120.6(9) . . ?
F2 C3 C35 92.4(5) . 1_655 ?
C4 C3 C35 85.1(6) . 1_655 ?
C2 C3 C35 93.0(6) . 1_655 ?
C5 C4 C3 118.2(8) . . ?
C5 C4 I2 121.2(7) . . ?
C3 C4 I2 120.6(8) . . ?
F3 C5 C6 120.2(9) . . ?
F3 C5 C4 120.5(8) . . ?
C6 C5 C4 119.3(8) . . ?
C5 C6 C1 126.2(8) . . ?
C5 C6 F4 116.6(8) . . ?
C1 C6 F4 117.1(7) . . ?
C12 C7 C8 117.8(8) . . ?
C12 C7 I3 120.6(7) . . ?
C8 C7 I3 121.5(7) . . ?
F5 C8 C7 120.4(8) . . ?
F5 C8 C9 118.3(9) . . ?
C7 C8 C9 121.2(9) . . ?
F6 C9 C8 118.9(9) . . ?
F6 C9 C10 120.2(8) . . ?
C8 C9 C10 120.8(9) . . ?
C9 C10 C11 117.3(8) . . ?
C9 C10 I4 121.9(7) . . ?
C11 C10 I4 120.8(6) . . ?
C9 C10 C24 97.1(6) . 1_655 ?
C11 C10 C24 87.3(5) . 1_655 ?
I4 C10 C24 84.5(3) . 1_655 ?
F7 C11 C12 120.3(9) . . ?
F7 C11 C10 119.2(8) . . ?
C12 C11 C10 120.5(8) . . ?
C11 C12 F8 118.0(9) . . ?
C11 C12 C7 122.3(9) . . ?
F8 C12 C7 119.6(9) . . ?
C11 C12 C22 88.8(6) . 1_655 ?
F8 C12 C22 93.4(5) . 1_655 ?
C7 C12 C22 87.7(6) . 1_655 ?
N1 C13 C22 122.8(9) . . ?
N1 C13 C14 119.3(8) . . ?
C22 C13 C14 117.8(8) . . ?
C15 C14 C13 121.4(8) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C16 122.9(9) . . ?
C14 C15 H15 118.6 . . ?
C16 C15 H15 118.6 . . ?
C17 C16 C15 123.4(9) . . ?
C17 C16 C21 118.0(9) . . ?
C15 C16 C21 118.6(8) . . ?
C18 C17 C16 123.3(10) . . ?
C18 C17 H17 118.4 . . ?
C16 C17 H17 118.4 . . ?
C17 C18 C19 119.2(9) . . ?
C17 C18 H18 120.4 . . ?
C19 C18 H18 120.4 . . ?
C20 C19 C18 120.4(11) . . ?
C20 C19 H19 119.8 . . ?
C18 C19 H19 119.8 . . ?
C19 C20 C21 121.2(10) . . ?
C19 C20 H20 119.4 . . ?
C21 C20 H20 119.4 . . ?
C20 C21 C16 117.7(8) . . ?
C20 C21 C22 123.8(8) . . ?
C16 C21 C22 118.5(8) . . ?
C13 C22 C23 116.2(7) . . ?
C13 C22 C21 120.7(8) . . ?
C23 C22 C21 123.0(8) . . ?
C24 C23 C22 118.7(9) . . ?
C24 C23 H23 120.7 . . ?
C22 C23 H23 120.7 . . ?
C23 C24 C25 120.4(9) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 H24 119.8 . . ?
N1 C25 C24 123.1(9) . . ?
N1 C25 H25 118.5 . . ?
C24 C25 H25 118.5 . . ?
N2 C26 C35 123.6(9) . . ?
N2 C26 C27 116.7(8) . . ?
C35 C26 C27 119.7(8) . . ?
C28 C27 C26 120.9(9) . . ?
C28 C27 H27 119.6 . . ?
C26 C27 H27 119.6 . . ?
C27 C28 C29 121.3(10) . . ?
C27 C28 H28 119.3 . . ?
C29 C28 H28 119.3 . . ?
C30 C29 C34 121.2(9) . . ?
C30 C29 C28 120.1(10) . . ?
C34 C29 C28 118.7(8) . . ?
C31 C30 C29 119.2(11) . . ?
C31 C30 H30 120.4 . . ?
C29 C30 H30 120.4 . . ?
C30 C31 C32 120.6(10) . . ?
C30 C31 H31 119.7 . . ?
C32 C31 H31 119.7 . . ?
C33 C32 C31 119.7(10) . . ?
C33 C32 H32 120.2 . . ?
C31 C32 H32 120.2 . . ?
C32 C33 C34 121.9(10) . . ?
C32 C33 H33 119.1 . . ?
C34 C33 H33 119.1 . . ?
C33 C34 C29 117.3(8) . . ?
C33 C34 C35 124.0(9) . . ?
C29 C34 C35 118.7(8) . . ?
C26 C35 C36 116.1(8) . . ?
C26 C35 C34 120.7(9) . . ?
C36 C35 C34 123.2(8) . . ?
C37 C36 C35 119.9(9) . . ?
C37 C36 H36 120.1 . . ?
C35 C36 H36 120.1 . . ?
C38 C37 C36 118.6(9) . . ?
C38 C37 H37 120.7 . . ?
C36 C37 H37 120.7 . . ?
N2 C38 C37 123.9(9) . . ?
N2 C38 H38 118.1 . . ?
C37 C38 H38 118.1 . . ?
C1 I1 N2 171.6(3) . 2_556 ?
C4 I2 I3 166.3(2) . . ?
C7 I3 C31 171.4(4) . 1_655 ?
C7 I3 I2 115.3(2) . . ?
C31 I3 I2 67.41(18) 1_655 . ?
C10 I4 N1 171.7(3) . 2_647 ?
C25 N1 C13 118.8(9) . . ?
C38 N2 C26 117.9(9) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.968
_refine_diff_density_min         -0.616
_refine_diff_density_rms         0.097
_database_code_depnum_ccdc_archive 'CCDC 975981'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_120706a_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H9 F6 I3 N'
_chemical_formula_weight         782.00

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'
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           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.354(2)
_cell_length_b                   10.731(3)
_cell_length_c                   12.901(3)
_cell_angle_alpha                87.896(4)
_cell_angle_beta                 86.296(4)
_cell_angle_gamma                83.292(4)
_cell_volume                     1145.7(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2520
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      25.20

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.267
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             722
_exptl_absorpt_coefficient_mu    4.151
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.3594
_exptl_absorpt_correction_T_max  0.6816
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_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  '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_%        ?
_diffrn_reflns_number            5590
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_av_sigmaI/netI    0.0359
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.45
_diffrn_reflns_theta_max         25.25
_reflns_number_total             4098
_reflns_number_gt                3374
_reflns_threshold_expression     >2sigma(I)

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

_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     
'calc w=1/[σ²(Fo²)+(0.0329P)²+1.9801P] where P=(Fo²+2Fc²)/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         4098
_refine_ls_number_parameters     289
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0443
_refine_ls_R_factor_gt           0.0351
_refine_ls_wR_factor_ref         0.0891
_refine_ls_wR_factor_gt          0.0826
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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 0.5901(7) 0.1726(5) 1.0574(5) 0.0560(14) Uani 1 1 d . . .
C2 C 0.5701(7) 0.1596(5) 0.9535(5) 0.0564(14) Uani 1 1 d . . .
C3 C 0.6996(7) 0.1521(5) 0.8793(5) 0.0550(13) Uani 1 1 d . . .
C4 C 0.8549(7) 0.1575(5) 0.9099(5) 0.0552(13) Uani 1 1 d . . .
C5 C 0.8758(7) 0.1699(6) 1.0128(5) 0.0641(16) Uani 1 1 d . . .
C6 C 0.7452(7) 0.1779(5) 1.0861(5) 0.0605(15) Uani 1 1 d . . .
C7 C 0.4575(7) 0.4850(5) 0.8978(4) 0.0514(13) Uani 1 1 d . . .
C8 C 0.6161(7) 0.4800(5) 0.9224(4) 0.0560(14) Uani 1 1 d . . .
C9 C 0.6566(7) 0.4956(5) 1.0225(4) 0.0551(13) Uani 1 1 d . . .
C10 C 0.2775(7) 0.5641(6) 0.4973(5) 0.0625(15) Uani 1 1 d . . .
H10 H 0.3284 0.6209 0.5326 0.075 Uiso 1 1 calc R . .
C11 C 0.1804(7) 0.6106(6) 0.4173(5) 0.0670(16) Uani 1 1 d . . .
H11 H 0.1662 0.6962 0.4010 0.080 Uiso 1 1 calc R . .
C12 C 0.1077(7) 0.5298(7) 0.3641(4) 0.0649(16) Uani 1 1 d . . .
H12 H 0.0409 0.5595 0.3115 0.078 Uiso 1 1 calc R . .
C13 C 0.1330(6) 0.4002(6) 0.3883(4) 0.0546(13) Uani 1 1 d . . .
C14 C 0.0607(7) 0.3109(7) 0.3333(5) 0.0671(17) Uani 1 1 d . . .
H14 H -0.0023 0.3376 0.2780 0.080 Uiso 1 1 calc R . .
C15 C 0.0832(7) 0.1864(7) 0.3611(5) 0.0693(17) Uani 1 1 d . . .
H15 H 0.0347 0.1292 0.3247 0.083 Uiso 1 1 calc R . .
C16 C 0.1807(6) 0.1424(6) 0.4458(5) 0.0606(15) Uani 1 1 d . . .
C17 C 0.2024(8) 0.0137(7) 0.4756(6) 0.0762(18) Uani 1 1 d . . .
H17 H 0.1545 -0.0438 0.4392 0.091 Uiso 1 1 calc R . .
C18 C 0.2928(8) -0.0273(7) 0.5572(6) 0.078(2) Uani 1 1 d . . .
H18 H 0.3045 -0.1121 0.5764 0.094 Uiso 1 1 calc R . .
C19 C 0.3676(8) 0.0570(6) 0.6119(5) 0.0720(17) Uani 1 1 d . . .
H19 H 0.4292 0.0282 0.6673 0.086 Uiso 1 1 calc R . .
C20 C 0.3507(7) 0.1820(6) 0.5846(4) 0.0578(14) Uani 1 1 d . . .
H20 H 0.4021 0.2374 0.6210 0.069 Uiso 1 1 calc R . .
C21 C 0.2557(6) 0.2281(5) 0.5012(4) 0.0500(12) Uani 1 1 d . . .
C22 C 0.2312(6) 0.3610(5) 0.4718(4) 0.0470(12) Uani 1 1 d . . .
F1 F 0.4222(4) 0.1536(4) 0.9196(3) 0.0832(11) Uani 1 1 d . . .
F2 F 0.6727(5) 0.1425(4) 0.7796(3) 0.0812(10) Uani 1 1 d . . .
F3 F 1.0236(4) 0.1747(5) 1.0465(3) 0.0973(13) Uani 1 1 d . . .
F4 F 0.7729(5) 0.1911(4) 1.1866(3) 0.0874(11) Uani 1 1 d . . .
F5 F 0.7377(4) 0.4610(4) 0.8482(3) 0.0774(10) Uani 1 1 d . . .
F6 F 0.8164(5) 0.4888(4) 1.0412(3) 0.0833(11) Uani 1 1 d . . .
I1 I 0.39381(5) 0.18740(4) 1.16662(4) 0.07037(15) Uani 1 1 d . . .
I2 I 1.05071(5) 0.14638(4) 0.79904(4) 0.07660(16) Uani 1 1 d . . .
I3 I 0.39797(5) 0.46412(4) 0.74442(3) 0.06534(14) Uani 1 1 d . . .
N1 N 0.3015(5) 0.4436(4) 0.5260(3) 0.0526(11) Uani 1 1 d . . .


_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 1.376(8) . ?
C1 C6 1.378(8) . ?
C1 I1 2.087(6) . ?
C2 F1 1.346(6) . ?
C2 C3 1.395(8) . ?
C3 F2 1.330(6) . ?
C3 C4 1.388(8) . ?
C4 C5 1.363(8) . ?
C4 I2 2.098(6) . ?
C5 F3 1.343(6) . ?
C5 C6 1.393(9) . ?
C6 F4 1.347(7) . ?
C7 C9 1.361(8) 2_667 ?
C7 C8 1.377(8) . ?
C7 I3 2.097(5) . ?
C8 F5 1.353(6) . ?
C8 C9 1.377(8) . ?
C9 C7 1.361(8) 2_667 ?
C9 F6 1.365(7) . ?
C10 N1 1.328(7) . ?
C10 C11 1.395(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.346(9) . ?
C11 H11 0.9300 . ?
C12 C13 1.408(9) . ?
C12 F5 2.955(6) 2_666 ?
C12 H12 0.9300 . ?
C13 C22 1.418(7) . ?
C13 C14 1.425(8) . ?
C14 C15 1.365(9) . ?
C14 I1 3.564(6) 1_554 ?
C14 H14 0.9300 . ?
C15 C16 1.438(9) . ?
C15 I1 3.492(6) 1_554 ?
C15 H15 0.9300 . ?
C16 C21 1.410(8) . ?
C16 C17 1.414(9) . ?
C17 C18 1.364(10) . ?
C17 H17 0.9300 . ?
C18 C19 1.394(10) . ?
C18 H18 0.9300 . ?
C19 C20 1.368(8) . ?
C19 I2 3.536(6) 1_455 ?
C19 H19 0.9300 . ?
C20 C21 1.418(7) . ?
C20 I2 3.651(6) 1_455 ?
C20 I3 3.797(6) . ?
C20 H20 0.9300 . ?
C21 C22 1.457(8) . ?
C22 N1 1.356(7) . ?
F5 C12 2.955(6) 2_666 ?
I1 C15 3.492(6) 1_556 ?
I1 C14 3.564(6) 1_556 ?
I2 C19 3.536(6) 1_655 ?
I2 C20 3.651(6) 1_655 ?
I3 N1 3.003(5) . ?

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 C6 117.1(6) . . ?
C2 C1 I1 121.5(4) . . ?
C6 C1 I1 121.4(5) . . ?
F1 C2 C1 120.5(5) . . ?
F1 C2 C3 117.2(5) . . ?
C1 C2 C3 122.2(5) . . ?
F2 C3 C4 120.6(5) . . ?
F2 C3 C2 119.6(5) . . ?
C4 C3 C2 119.7(5) . . ?
C5 C4 C3 118.4(5) . . ?
C5 C4 I2 121.5(4) . . ?
C3 C4 I2 120.1(4) . . ?
F3 C5 C4 120.8(6) . . ?
F3 C5 C6 117.9(6) . . ?
C4 C5 C6 121.3(5) . . ?
F4 C6 C1 120.0(6) . . ?
F4 C6 C5 118.7(5) . . ?
C1 C6 C5 121.3(6) . . ?
C9 C7 C8 116.6(5) 2_667 . ?
C9 C7 I3 122.4(4) 2_667 . ?
C8 C7 I3 121.0(4) . . ?
F5 C8 C9 117.8(5) . . ?
F5 C8 C7 120.7(5) . . ?
C9 C8 C7 121.5(5) . . ?
C7 C9 F6 119.9(5) 2_667 . ?
C7 C9 C8 121.9(5) 2_667 . ?
F6 C9 C8 118.2(5) . . ?
N1 C10 C11 123.9(6) . . ?
N1 C10 H10 118.1 . . ?
C11 C10 H10 118.1 . . ?
C12 C11 C10 119.0(6) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C11 C12 C13 119.8(6) . . ?
C11 C12 F5 104.7(4) . 2_666 ?
C13 C12 F5 101.0(4) . 2_666 ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
F5 C12 H12 63.7 2_666 . ?
C12 C13 C22 117.5(5) . . ?
C12 C13 C14 121.9(6) . . ?
C22 C13 C14 120.5(6) . . ?
C15 C14 C13 120.4(6) . . ?
C15 C14 I1 75.9(4) . 1_554 ?
C13 C14 I1 100.9(3) . 1_554 ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
I1 C14 H14 93.1 1_554 . ?
C14 C15 C16 121.0(6) . . ?
C14 C15 I1 81.8(4) . 1_554 ?
C16 C15 I1 97.8(3) . 1_554 ?
C14 C15 H15 119.5 . . ?
C16 C15 H15 119.5 . . ?
I1 C15 H15 90.4 1_554 . ?
C21 C16 C17 118.9(6) . . ?
C21 C16 C15 120.1(6) . . ?
C17 C16 C15 121.1(6) . . ?
C18 C17 C16 120.8(6) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C17 C18 C19 120.5(6) . . ?
C17 C18 H18 119.8 . . ?
C19 C18 H18 119.8 . . ?
C20 C19 C18 120.3(6) . . ?
C20 C19 I2 83.8(4) . 1_455 ?
C18 C19 I2 99.2(4) . 1_455 ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
I2 C19 H19 87.0 1_455 . ?
C19 C20 C21 120.7(6) . . ?
C19 C20 I2 74.3(4) . 1_455 ?
C21 C20 I2 103.2(3) . 1_455 ?
C19 C20 I3 129.8(4) . . ?
C21 C20 I3 106.2(4) . . ?
I2 C20 I3 78.90(11) 1_455 . ?
C19 C20 H20 119.6 . . ?
C21 C20 H20 119.6 . . ?
I2 C20 H20 92.4 1_455 . ?
I3 C20 H20 21.6 . . ?
C16 C21 C20 118.8(5) . . ?
C16 C21 C22 118.9(5) . . ?
C20 C21 C22 122.3(5) . . ?
N1 C22 C13 122.0(5) . . ?
N1 C22 C21 118.9(5) . . ?
C13 C22 C21 119.0(5) . . ?
C8 F5 C12 156.0(4) . 2_666 ?
C1 I1 C15 174.50(19) . 1_556 ?
C1 I1 C14 162.62(18) . 1_556 ?
C15 I1 C14 22.29(15) 1_556 1_556 ?
C4 I2 C19 167.37(19) . 1_655 ?
C4 I2 C20 168.94(17) . 1_655 ?
C19 I2 C20 21.86(13) 1_655 1_655 ?
C7 I3 N1 177.52(17) . . ?
C7 I3 C20 133.63(16) . . ?
N1 I3 C20 48.21(12) . . ?
C10 N1 C22 117.7(5) . . ?
C10 N1 I3 100.5(4) . . ?
C22 N1 I3 137.0(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 F1 179.9(5) . . . . ?
I1 C1 C2 F1 -1.4(7) . . . . ?
C6 C1 C2 C3 0.0(8) . . . . ?
I1 C1 C2 C3 178.7(4) . . . . ?
F1 C2 C3 F2 1.6(8) . . . . ?
C1 C2 C3 F2 -178.5(5) . . . . ?
F1 C2 C3 C4 -179.8(5) . . . . ?
C1 C2 C3 C4 0.1(8) . . . . ?
F2 C3 C4 C5 178.7(5) . . . . ?
C2 C3 C4 C5 0.1(8) . . . . ?
F2 C3 C4 I2 -1.4(7) . . . . ?
C2 C3 C4 I2 -180.0(4) . . . . ?
C3 C4 C5 F3 179.5(5) . . . . ?
I2 C4 C5 F3 -0.3(8) . . . . ?
C3 C4 C5 C6 -0.4(9) . . . . ?
I2 C4 C5 C6 179.7(4) . . . . ?
C2 C1 C6 F4 179.7(5) . . . . ?
I1 C1 C6 F4 0.9(7) . . . . ?
C2 C1 C6 C5 -0.3(8) . . . . ?
I1 C1 C6 C5 -179.0(4) . . . . ?
F3 C5 C6 F4 0.6(9) . . . . ?
C4 C5 C6 F4 -179.4(5) . . . . ?
F3 C5 C6 C1 -179.5(5) . . . . ?
C4 C5 C6 C1 0.5(9) . . . . ?
C9 C7 C8 F5 180.0(5) 2_667 . . . ?
I3 C7 C8 F5 -0.3(7) . . . . ?
C9 C7 C8 C9 -0.9(9) 2_667 . . . ?
I3 C7 C8 C9 178.9(4) . . . . ?
F5 C8 C9 C7 -179.9(5) . . . 2_667 ?
C7 C8 C9 C7 0.9(9) . . . 2_667 ?
F5 C8 C9 F6 -1.2(8) . . . . ?
C7 C8 C9 F6 179.7(5) . . . . ?
N1 C10 C11 C12 -1.0(9) . . . . ?
C10 C11 C12 C13 -1.3(9) . . . . ?
C10 C11 C12 F5 -113.5(5) . . . 2_666 ?
C11 C12 C13 C22 2.3(8) . . . . ?
F5 C12 C13 C22 116.5(4) 2_666 . . . ?
C11 C12 C13 C14 -179.1(5) . . . . ?
F5 C12 C13 C14 -65.0(5) 2_666 . . . ?
C12 C13 C14 C15 -177.7(5) . . . . ?
C22 C13 C14 C15 0.8(8) . . . . ?
C12 C13 C14 I1 102.4(5) . . . 1_554 ?
C22 C13 C14 I1 -79.1(5) . . . 1_554 ?
C13 C14 C15 C16 -0.4(9) . . . . ?
I1 C14 C15 C16 94.2(5) 1_554 . . . ?
C13 C14 C15 I1 -94.6(5) . . . 1_554 ?
C14 C15 C16 C21 -0.4(9) . . . . ?
I1 C15 C16 C21 84.7(5) 1_554 . . . ?
C14 C15 C16 C17 179.2(6) . . . . ?
I1 C15 C16 C17 -95.8(5) 1_554 . . . ?
C21 C16 C17 C18 0.7(9) . . . . ?
C15 C16 C17 C18 -178.9(6) . . . . ?
C16 C17 C18 C19 -0.9(10) . . . . ?
C17 C18 C19 C20 0.2(10) . . . . ?
C17 C18 C19 I2 88.4(6) . . . 1_455 ?
C18 C19 C20 C21 0.8(9) . . . . ?
I2 C19 C20 C21 -96.3(5) 1_455 . . . ?
C18 C19 C20 I2 97.1(6) . . . 1_455 ?
C18 C19 C20 I3 157.5(5) . . . . ?
I2 C19 C20 I3 60.4(4) 1_455 . . . ?
C17 C16 C21 C20 0.3(8) . . . . ?
C15 C16 C21 C20 179.8(5) . . . . ?
C17 C16 C21 C22 -178.9(5) . . . . ?
C15 C16 C21 C22 0.6(8) . . . . ?
C19 C20 C21 C16 -1.0(8) . . . . ?
I2 C20 C21 C16 -80.5(5) 1_455 . . . ?
I3 C20 C21 C16 -162.6(4) . . . . ?
C19 C20 C21 C22 178.2(5) . . . . ?
I2 C20 C21 C22 98.7(5) 1_455 . . . ?
I3 C20 C21 C22 16.7(5) . . . . ?
C12 C13 C22 N1 -1.2(7) . . . . ?
C14 C13 C22 N1 -179.8(5) . . . . ?
C12 C13 C22 C21 178.0(5) . . . . ?
C14 C13 C22 C21 -0.6(7) . . . . ?
C16 C21 C22 N1 179.1(5) . . . . ?
C20 C21 C22 N1 -0.1(7) . . . . ?
C16 C21 C22 C13 -0.1(7) . . . . ?
C20 C21 C22 C13 -179.3(5) . . . . ?
C9 C8 F5 C12 -151.6(7) . . . 2_666 ?
C7 C8 F5 C12 27.6(12) . . . 2_666 ?
C2 C1 I1 C15 120.9(19) . . . 1_556 ?
C6 C1 I1 C15 -60(2) . . . 1_556 ?
C2 C1 I1 C14 -89.8(8) . . . 1_556 ?
C6 C1 I1 C14 88.9(7) . . . 1_556 ?
C5 C4 I2 C19 106.0(9) . . . 1_655 ?
C3 C4 I2 C19 -73.9(10) . . . 1_655 ?
C5 C4 I2 C20 -119.1(9) . . . 1_655 ?
C3 C4 I2 C20 61.1(12) . . . 1_655 ?
C9 C7 I3 N1 44(4) 2_667 . . . ?
C8 C7 I3 N1 -136(4) . . . . ?
C9 C7 I3 C20 -93.0(5) 2_667 . . . ?
C8 C7 I3 C20 87.2(5) . . . . ?
C19 C20 I3 C7 0.5(6) . . . . ?
C21 C20 I3 C7 159.7(3) . . . . ?
I2 C20 I3 C7 59.0(3) 1_455 . . . ?
C19 C20 I3 N1 -177.3(6) . . . . ?
C21 C20 I3 N1 -18.0(3) . . . . ?
I2 C20 I3 N1 -118.72(17) 1_455 . . . ?
C11 C10 N1 C22 2.2(8) . . . . ?
C11 C10 N1 I3 -157.3(5) . . . . ?
C13 C22 N1 C10 -1.0(7) . . . . ?
C21 C22 N1 C10 179.8(5) . . . . ?
C13 C22 N1 I3 148.7(4) . . . . ?
C21 C22 N1 I3 -30.5(7) . . . . ?
C7 I3 N1 C10 41(4) . . . . ?
C20 I3 N1 C10 179.8(4) . . . . ?
C7 I3 N1 C22 -112(4) . . . . ?
C20 I3 N1 C22 26.8(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C20 H20 I3 0.93 2.95 3.797(6) 151.8 .

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        25.25
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         1.460
_refine_diff_density_min         -1.052
_refine_diff_density_rms         0.090
_database_code_depnum_ccdc_archive 'CCDC 975982'
