# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2015

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_120319e_0m
_database_code_depnum_ccdc_archive 'CCDC 1014498'
_audit_update_record             
;
2015-02-03 deposited with the CCDC.
2015-05-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C11 H18 F4 I N O'
_chemical_formula_weight         383.16

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'
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                   5.7245(8)
_cell_length_b                   11.1337(17)
_cell_length_c                   12.3817(19)
_cell_angle_alpha                66.474(2)
_cell_angle_beta                 87.523(2)
_cell_angle_gamma                89.655(2)
_cell_volume                     722.82(19)
_cell_formula_units_Z            2
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    3384
_cell_measurement_theta_min      0.00
_cell_measurement_theta_max      0.00

_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    1.760
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376
_exptl_absorpt_coefficient_mu    2.248
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7291
_exptl_absorpt_correction_T_max  0.8064
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      110(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            3593
_diffrn_reflns_av_R_equivalents  0.0141
_diffrn_reflns_av_sigmaI/netI    0.0246
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.00
_diffrn_reflns_theta_max         25.24
_reflns_number_total             2565
_reflns_number_gt                2477
_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)+(0.0182P)²+0.7054P] 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         2565
_refine_ls_number_parameters     167
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0206
_refine_ls_R_factor_gt           0.0197
_refine_ls_wR_factor_ref         0.0475
_refine_ls_wR_factor_gt          0.0469
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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 0.8998(5) 0.1339(3) 0.8454(2) 0.0294(6) Uani 1 1 d . . .
C2 C 0.9468(4) 0.0695(2) 0.9776(2) 0.0193(5) Uani 1 1 d . . .
C3 C 0.3951(4) 0.7115(2) 0.7813(2) 0.0182(5) Uani 1 1 d . . .
C4 C 0.2416(4) 0.5935(3) 0.8568(2) 0.0250(5) Uani 1 1 d . . .
H4A H 0.1097 0.5870 0.8114 0.037 Uiso 1 1 calc R . .
H4B H 0.1826 0.6043 0.9278 0.037 Uiso 1 1 calc R . .
H4C H 0.3341 0.5135 0.8795 0.037 Uiso 1 1 calc R . .
C5 C 0.5872(4) 0.7306(3) 0.8553(2) 0.0250(5) Uani 1 1 d . . .
H5A H 0.6769 0.6499 0.8892 0.038 Uiso 1 1 calc R . .
H5B H 0.5161 0.7518 0.9189 0.038 Uiso 1 1 calc R . .
H5C H 0.6917 0.8025 0.8052 0.038 Uiso 1 1 calc R . .
C6 C 0.2530(4) 0.8370(2) 0.7297(2) 0.0217(5) Uani 1 1 d . . .
H6A H 0.1496 0.8442 0.7930 0.026 Uiso 1 1 calc R . .
H6B H 0.3613 0.9134 0.7006 0.026 Uiso 1 1 calc R . .
C7 C 0.1046(4) 0.8415(2) 0.6293(2) 0.0219(5) Uani 1 1 d . . .
H7A H 0.0120 0.9228 0.6009 0.026 Uiso 1 1 calc R . .
H7B H -0.0051 0.7657 0.6572 0.026 Uiso 1 1 calc R . .
C8 C 0.2645(4) 0.8375(2) 0.5295(2) 0.0199(5) Uani 1 1 d . . .
H8A H 0.3702 0.9150 0.5011 0.024 Uiso 1 1 calc R . .
H8B H 0.1682 0.8431 0.4632 0.024 Uiso 1 1 calc R . .
C9 C 0.4115(4) 0.7137(2) 0.5658(2) 0.0181(5) Uani 1 1 d . . .
C10 C 0.2642(4) 0.5949(2) 0.5756(2) 0.0238(5) Uani 1 1 d . . .
H10A H 0.3571 0.5152 0.6091 0.036 Uiso 1 1 calc R . .
H10B H 0.2165 0.6061 0.4971 0.036 Uiso 1 1 calc R . .
H10C H 0.1250 0.5873 0.6269 0.036 Uiso 1 1 calc R . .
C11 C 0.6156(4) 0.7350(3) 0.4757(2) 0.0252(5) Uani 1 1 d . . .
H11A H 0.7191 0.8044 0.4765 0.038 Uiso 1 1 calc R . .
H11B H 0.5551 0.7606 0.3969 0.038 Uiso 1 1 calc R . .
H11C H 0.7034 0.6536 0.4962 0.038 Uiso 1 1 calc R . .
F1 F 0.7431(4) 0.06047(17) 0.82031(18) 0.0630(7) Uani 1 1 d . . .
F2 F 1.0963(4) 0.13607(19) 0.78281(16) 0.0647(7) Uani 1 1 d . . .
F3 F 0.7406(3) 0.06211(15) 1.03633(14) 0.0324(4) Uani 1 1 d . . .
F4 F 1.0901(3) 0.14754(14) 1.00346(15) 0.0341(4) Uani 1 1 d . . .
I1 I 0.77290(3) 0.329934(14) 0.794365(13) 0.02268(7) Uani 1 1 d . . .
N1 N 0.5128(3) 0.68483(18) 0.68301(17) 0.0158(4) Uani 1 1 d . . .
O1 O 0.6764(3) 0.59922(16) 0.71231(15) 0.0217(4) 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 F2 1.333(3) . ?
C1 F1 1.343(3) . ?
C1 C2 1.538(3) . ?
C1 I1 2.147(3) . ?
C2 F4 1.335(3) . ?
C2 F3 1.345(3) . ?
C2 C2 1.552(5) 2_757 ?
C3 N1 1.496(3) . ?
C3 C4 1.528(3) . ?
C3 C5 1.529(3) . ?
C3 C6 1.530(3) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 C7 1.520(3) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.521(3) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.528(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 N1 1.498(3) . ?
C9 C11 1.531(3) . ?
C9 C10 1.534(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
N1 O1 1.288(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
F2 C1 F1 107.2(2) . . ?
F2 C1 C2 109.3(2) . . ?
F1 C1 C2 109.0(2) . . ?
F2 C1 I1 109.37(18) . . ?
F1 C1 I1 109.78(18) . . ?
C2 C1 I1 112.05(16) . . ?
F4 C2 F3 108.26(19) . . ?
F4 C2 C1 108.7(2) . . ?
F3 C2 C1 106.9(2) . . ?
F4 C2 C2 108.3(2) . 2_757 ?
F3 C2 C2 108.3(2) . 2_757 ?
C1 C2 C2 116.3(2) . 2_757 ?
N1 C3 C4 108.93(19) . . ?
N1 C3 C5 107.34(18) . . ?
C4 C3 C5 109.8(2) . . ?
N1 C3 C6 109.31(19) . . ?
C4 C3 C6 111.9(2) . . ?
C5 C3 C6 109.5(2) . . ?
C3 C4 H4A 109.5 . . ?
C3 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C3 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C3 C5 H5A 109.5 . . ?
C3 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C3 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C7 C6 C3 113.0(2) . . ?
C7 C6 H6A 109.0 . . ?
C3 C6 H6A 109.0 . . ?
C7 C6 H6B 109.0 . . ?
C3 C6 H6B 109.0 . . ?
H6A C6 H6B 107.8 . . ?
C6 C7 C8 109.0(2) . . ?
C6 C7 H7A 109.9 . . ?
C8 C7 H7A 109.9 . . ?
C6 C7 H7B 109.9 . . ?
C8 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
C7 C8 C9 113.1(2) . . ?
C7 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
N1 C9 C8 110.05(18) . . ?
N1 C9 C11 107.57(18) . . ?
C8 C9 C11 109.6(2) . . ?
N1 C9 C10 108.29(19) . . ?
C8 C9 C10 111.4(2) . . ?
C11 C9 C10 109.9(2) . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 N1 C3 116.11(18) . . ?
O1 N1 C9 115.81(17) . . ?
C3 N1 C9 125.04(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
F2 C1 C2 F4 67.4(3) . . . . ?
F1 C1 C2 F4 -175.8(2) . . . . ?
I1 C1 C2 F4 -54.1(2) . . . . ?
F2 C1 C2 F3 -176.0(2) . . . . ?
F1 C1 C2 F3 -59.2(3) . . . . ?
I1 C1 C2 F3 62.5(2) . . . . ?
F2 C1 C2 C2 -55.1(3) . . . 2_757 ?
F1 C1 C2 C2 61.8(3) . . . 2_757 ?
I1 C1 C2 C2 -176.5(2) . . . 2_757 ?
N1 C3 C6 C7 46.8(3) . . . . ?
C4 C3 C6 C7 -74.0(3) . . . . ?
C5 C3 C6 C7 164.1(2) . . . . ?
C3 C6 C7 C8 -61.6(3) . . . . ?
C6 C7 C8 C9 60.3(3) . . . . ?
C7 C8 C9 N1 -44.7(3) . . . . ?
C7 C8 C9 C11 -162.8(2) . . . . ?
C7 C8 C9 C10 75.4(3) . . . . ?
C4 C3 N1 O1 -71.7(2) . . . . ?
C5 C3 N1 O1 47.1(3) . . . . ?
C6 C3 N1 O1 165.78(19) . . . . ?
C4 C3 N1 C9 87.6(3) . . . . ?
C5 C3 N1 C9 -153.5(2) . . . . ?
C6 C3 N1 C9 -34.9(3) . . . . ?
C8 C9 N1 O1 -166.61(19) . . . . ?
C11 C9 N1 O1 -47.2(3) . . . . ?
C10 C9 N1 O1 71.5(2) . . . . ?
C8 C9 N1 C3 34.0(3) . . . . ?
C11 C9 N1 C3 153.4(2) . . . . ?
C10 C9 N1 C3 -87.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.984
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.984
_refine_diff_density_max         0.590
_refine_diff_density_min         -0.511
_refine_diff_density_rms         0.071
