# 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

#######################################################################
#
#                 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_a
#TrackingRef '291205C.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H19 F N3 O3, I3'
_chemical_formula_sum            'C17 H19 F I3 N3 O3'
_chemical_formula_weight         713.05

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'P-1 '
_symmetry_space_group_name_Hall  '-P 1'

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

_cell_length_a                   8.1001(7)
_cell_length_b                   9.6437(8)
_cell_length_c                   13.9228(12)
_cell_angle_alpha                87.4810(10)
_cell_angle_beta                 77.694(2)
_cell_angle_gamma                77.2790(10)
_cell_volume                     1036.50(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    291(2)
_cell_measurement_reflns_used    2361
_cell_measurement_theta_min      2.11
_cell_measurement_theta_max      26.99

_exptl_crystal_description       block
_exptl_crystal_colour            violet
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.285
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             668
_exptl_absorpt_coefficient_mu    4.555
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4340
_exptl_absorpt_correction_T_max  0.4944
_exptl_absorpt_process_details   'SADABS; Bruker, 2000'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      291(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Smart Apex CCD'
_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            5717
_diffrn_reflns_av_R_equivalents  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0711
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3996
_reflns_number_gt                2436
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       SMART
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  SHELXTL
_computing_molecular_graphics    SHELXTL
_computing_publication_material  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)+(0.05P)²+1.22P] 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         3996
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0866
_refine_ls_R_factor_gt           0.0559
_refine_ls_wR_factor_ref         0.1159
_refine_ls_wR_factor_gt          0.1106
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6523(11) 0.8100(9) -0.1686(7) 0.043(2) Uani 1 1 d . . .
C2 C 0.6306(10) 0.8119(8) -0.0615(6) 0.0331(17) Uani 1 1 d . . .
C3 C 0.7218(10) 0.9016(9) -0.0188(6) 0.0374(18) Uani 1 1 d . . .
C4 C 0.7046(10) 0.8905(8) 0.0856(6) 0.0354(18) Uani 1 1 d . . .
C5 C 0.7878(11) 0.9666(11) 0.1362(6) 0.048(2) Uani 1 1 d . . .
H5 H 0.8514 1.0289 0.1015 0.058 Uiso 1 1 calc R . .
C6 C 0.7786(11) 0.9521(8) 0.2363(6) 0.0370(18) Uani 1 1 d . . .
C7 C 0.6836(10) 0.8621(8) 0.2911(6) 0.0366(17) Uani 1 1 d . . .
C8 C 0.5910(10) 0.7903(8) 0.2443(5) 0.0326(17) Uani 1 1 d . . .
H8 H 0.5211 0.7335 0.2804 0.039 Uiso 1 1 calc R . .
C9 C 0.6039(10) 0.8042(8) 0.1430(6) 0.0323(17) Uani 1 1 d . . .
C10 C 0.5316(11) 0.7365(9) -0.0034(6) 0.0396(19) Uani 1 1 d . . .
H10 H 0.4689 0.6868 -0.0325 0.047 Uiso 1 1 calc R . .
C11 C 0.4028(11) 0.6427(9) 0.1513(7) 0.045(2) Uani 1 1 d . . .
H11 H 0.4628 0.5492 0.1705 0.054 Uiso 1 1 calc R . .
C12 C 0.2437(12) 0.7063(9) 0.2230(6) 0.042(2) Uani 1 1 d . . .
H12A H 0.2138 0.8090 0.2298 0.050 Uiso 1 1 calc R . .
H12B H 0.2138 0.6544 0.2831 0.050 Uiso 1 1 calc R . .
C13 C 0.2316(10) 0.6445(9) 0.1290(6) 0.0362(18) Uani 1 1 d . . .
H13A H 0.1943 0.5551 0.1322 0.043 Uiso 1 1 calc R . .
H13B H 0.1943 0.7097 0.0789 0.043 Uiso 1 1 calc R . .
C14 C 0.8380(11) 0.8092(10) 0.4250(6) 0.0416(19) Uani 1 1 d . . .
H14A H 0.9147 0.8686 0.3916 0.050 Uiso 1 1 calc R . .
H14B H 0.8906 0.7113 0.4055 0.050 Uiso 1 1 calc R . .
C15 C 0.8163(11) 0.8236(9) 0.5340(6) 0.0375(18) Uani 1 1 d . . .
H15A H 0.9275 0.7919 0.5525 0.045 Uiso 1 1 calc R . .
H15B H 0.7721 0.9225 0.5532 0.045 Uiso 1 1 calc R . .
C16 C 0.5236(11) 0.7862(11) 0.5579(6) 0.047(2) Uani 1 1 d . . .
H16A H 0.4747 0.8845 0.5775 0.056 Uiso 1 1 calc R . .
H16B H 0.4449 0.7283 0.5913 0.056 Uiso 1 1 calc R . .
C17 C 0.5494(12) 0.7711(8) 0.4459(6) 0.041(2) Uani 1 1 d . . .
H17A H 0.5912 0.6716 0.4277 0.049 Uiso 1 1 calc R . .
H17B H 0.4393 0.8042 0.4265 0.049 Uiso 1 1 calc R . .
F1 F 0.8588(6) 1.0305(5) 0.2798(3) 0.0423(11) Uani 1 1 d . . .
I1 I 0.78414(9) 0.41692(7) 0.51910(5) 0.0577(2) Uani 1 1 d . . .
I2 I 0.84743(8) 0.41178(6) 0.31370(4) 0.04389(16) Uani 1 1 d . . .
I3 I 0.89113(8) 0.40501(7) 0.11241(4) 0.04914(18) Uani 1 1 d . . .
N1 N 0.5151(8) 0.7264(7) 0.0962(5) 0.0358(15) Uani 1 1 d . . .
N2 N 0.6706(9) 0.8510(8) 0.3950(5) 0.0410(16) Uani 1 1 d . . .
N3 N 0.6963(9) 0.7382(8) 0.5846(5) 0.0454(18) Uani 1 1 d . . .
H3A H 0.6844 0.7461 0.6500 0.055 Uiso 1 1 calc R . .
H3B H 0.7390 0.6462 0.5680 0.055 Uiso 1 1 calc R . .
O1 O 0.5899(8) 0.7274(7) -0.2096(4) 0.0450(14) Uani 1 1 d . . .
O2 O 0.7425(7) 0.8973(6) -0.2202(4) 0.0411(13) Uani 1 1 d . . .
H2D H 0.7637 0.9621 -0.1763 0.062 Uiso 1 1 d R . .
O3 O 0.8014(8) 0.9876(6) -0.0697(4) 0.0438(14) 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 O1 1.248(10) . ?
C1 O2 1.324(10) . ?
C1 C2 1.464(12) . ?
C2 C10 1.325(11) . ?
C2 C3 1.470(11) . ?
C3 O3 1.263(9) . ?
C3 C4 1.431(11) . ?
C4 C5 1.399(11) . ?
C4 C9 1.400(11) . ?
C5 C6 1.382(12) . ?
C5 H5 0.9300 . ?
C6 F1 1.336(9) . ?
C6 C7 1.383(11) . ?
C7 C8 1.394(11) . ?
C7 N2 1.429(11) . ?
C8 C9 1.394(10) . ?
C8 H8 0.9300 . ?
C9 N1 1.409(10) . ?
C10 N1 1.366(10) . ?
C10 H10 0.9300 . ?
C11 N1 1.428(10) . ?
C11 C12 1.480(13) . ?
C11 C13 1.481(11) . ?
C11 H11 0.9800 . ?
C12 C13 1.492(11) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 N2 1.470(11) . ?
C14 C15 1.500(11) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 N3 1.459(11) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 N3 1.493(11) . ?
C16 C17 1.538(11) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 N2 1.431(10) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
I1 I2 2.7964(10) . ?
I2 I3 2.7508(9) . ?
N3 H3A 0.9000 . ?
N3 H3B 0.9000 . ?
O2 H2D 0.9600 . ?

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
O1 C1 O2 121.3(8) . . ?
O1 C1 C2 121.0(7) . . ?
O2 C1 C2 117.7(7) . . ?
C10 C2 C1 122.0(7) . . ?
C10 C2 C3 120.0(7) . . ?
C1 C2 C3 118.1(7) . . ?
O3 C3 C4 122.5(8) . . ?
O3 C3 C2 122.4(8) . . ?
C4 C3 C2 115.0(7) . . ?
C5 C4 C9 116.0(7) . . ?
C5 C4 C3 121.5(7) . . ?
C9 C4 C3 122.5(7) . . ?
C6 C5 C4 122.1(8) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
F1 C6 C5 118.6(7) . . ?
F1 C6 C7 120.5(7) . . ?
C5 C6 C7 120.9(8) . . ?
C6 C7 C8 118.8(8) . . ?
C6 C7 N2 120.5(8) . . ?
C8 C7 N2 120.6(7) . . ?
C9 C8 C7 119.6(7) . . ?
C9 C8 H8 120.2 . . ?
C7 C8 H8 120.2 . . ?
C8 C9 C4 122.5(7) . . ?
C8 C9 N1 118.9(7) . . ?
C4 C9 N1 118.6(7) . . ?
C2 C10 N1 124.7(7) . . ?
C2 C10 H10 117.6 . . ?
N1 C10 H10 117.6 . . ?
N1 C11 C12 122.3(8) . . ?
N1 C11 C13 121.3(8) . . ?
C12 C11 C13 60.5(6) . . ?
N1 C11 H11 114.2 . . ?
C12 C11 H11 114.2 . . ?
C13 C11 H11 114.2 . . ?
C11 C12 C13 59.8(6) . . ?
C11 C12 H12A 117.8 . . ?
C13 C12 H12A 117.8 . . ?
C11 C12 H12B 117.8 . . ?
C13 C12 H12B 117.8 . . ?
H12A C12 H12B 114.9 . . ?
C11 C13 C12 59.7(6) . . ?
C11 C13 H13A 117.8 . . ?
C12 C13 H13A 117.8 . . ?
C11 C13 H13B 117.8 . . ?
C12 C13 H13B 117.8 . . ?
H13A C13 H13B 114.9 . . ?
N2 C14 C15 111.2(6) . . ?
N2 C14 H14A 109.4 . . ?
C15 C14 H14A 109.4 . . ?
N2 C14 H14B 109.4 . . ?
C15 C14 H14B 109.4 . . ?
H14A C14 H14B 108.0 . . ?
N3 C15 C14 109.6(7) . . ?
N3 C15 H15A 109.7 . . ?
C14 C15 H15A 109.7 . . ?
N3 C15 H15B 109.7 . . ?
C14 C15 H15B 109.7 . . ?
H15A C15 H15B 108.2 . . ?
N3 C16 C17 107.9(7) . . ?
N3 C16 H16A 110.1 . . ?
C17 C16 H16A 110.1 . . ?
N3 C16 H16B 110.1 . . ?
C17 C16 H16B 110.1 . . ?
H16A C16 H16B 108.4 . . ?
N2 C17 C16 111.2(7) . . ?
N2 C17 H17A 109.4 . . ?
C16 C17 H17A 109.4 . . ?
N2 C17 H17B 109.4 . . ?
C16 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
I3 I2 I1 176.81(3) . . ?
C10 N1 C9 119.0(7) . . ?
C10 N1 C11 119.6(7) . . ?
C9 N1 C11 121.3(7) . . ?
C7 N2 C17 115.6(7) . . ?
C7 N2 C14 114.2(6) . . ?
C17 N2 C14 111.6(7) . . ?
C15 N3 C16 110.6(7) . . ?
C15 N3 H3A 109.5 . . ?
C16 N3 H3A 109.5 . . ?
C15 N3 H3B 109.5 . . ?
C16 N3 H3B 109.5 . . ?
H3A N3 H3B 108.1 . . ?
C1 O2 H2D 109.1 . . ?

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
O1 C1 C2 C10 -6.3(13) . . . . ?
O2 C1 C2 C10 174.7(8) . . . . ?
O1 C1 C2 C3 174.1(8) . . . . ?
O2 C1 C2 C3 -4.9(11) . . . . ?
C10 C2 C3 O3 -171.7(8) . . . . ?
C1 C2 C3 O3 7.9(12) . . . . ?
C10 C2 C3 C4 4.6(11) . . . . ?
C1 C2 C3 C4 -175.8(7) . . . . ?
O3 C3 C4 C5 -5.4(12) . . . . ?
C2 C3 C4 C5 178.3(8) . . . . ?
O3 C3 C4 C9 174.3(8) . . . . ?
C2 C3 C4 C9 -2.0(11) . . . . ?
C9 C4 C5 C6 3.2(13) . . . . ?
C3 C4 C5 C6 -177.1(8) . . . . ?
C4 C5 C6 F1 -178.7(8) . . . . ?
C4 C5 C6 C7 -0.9(14) . . . . ?
F1 C6 C7 C8 175.2(7) . . . . ?
C5 C6 C7 C8 -2.7(12) . . . . ?
F1 C6 C7 N2 -0.3(12) . . . . ?
C5 C6 C7 N2 -178.1(8) . . . . ?
C6 C7 C8 C9 3.7(12) . . . . ?
N2 C7 C8 C9 179.1(7) . . . . ?
C7 C8 C9 C4 -1.3(11) . . . . ?
C7 C8 C9 N1 177.5(7) . . . . ?
C5 C4 C9 C8 -2.1(11) . . . . ?
C3 C4 C9 C8 178.2(7) . . . . ?
C5 C4 C9 N1 179.2(7) . . . . ?
C3 C4 C9 N1 -0.6(11) . . . . ?
C1 C2 C10 N1 175.5(8) . . . . ?
C3 C2 C10 N1 -4.9(13) . . . . ?
N1 C11 C12 C13 110.4(9) . . . . ?
N1 C11 C13 C12 -112.0(9) . . . . ?
N2 C14 C15 N3 57.1(9) . . . . ?
N3 C16 C17 N2 -57.5(10) . . . . ?
C2 C10 N1 C9 2.1(12) . . . . ?
C2 C10 N1 C11 179.4(8) . . . . ?
C8 C9 N1 C10 -178.0(7) . . . . ?
C4 C9 N1 C10 0.7(11) . . . . ?
C8 C9 N1 C11 4.7(11) . . . . ?
C4 C9 N1 C11 -176.5(7) . . . . ?
C12 C11 N1 C10 -113.7(9) . . . . ?
C13 C11 N1 C10 -41.0(12) . . . . ?
C12 C11 N1 C9 63.6(11) . . . . ?
C13 C11 N1 C9 136.3(8) . . . . ?
C6 C7 N2 C17 171.3(8) . . . . ?
C8 C7 N2 C17 -4.1(11) . . . . ?
C6 C7 N2 C14 -57.2(10) . . . . ?
C8 C7 N2 C14 127.4(8) . . . . ?
C16 C17 N2 C7 -170.7(7) . . . . ?
C16 C17 N2 C14 56.6(9) . . . . ?
C15 C14 N2 C7 170.4(7) . . . . ?
C15 C14 N2 C17 -56.2(9) . . . . ?
C14 C15 N3 C16 -59.9(9) . . . . ?
C17 C16 N3 C15 59.2(9) . . . . ?

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
N3 H3A O1 0.90 1.96 2.814(9) 159 1_556
N3 H3A O2 0.90 2.55 3.306(9) 142 1_556
N3 H3B I1 0.90 2.27 3.153(7) 167 .
O2 H2D O3 0.96 1.62 2.481(8) 147 .

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         1.091
_refine_diff_density_min         -1.088
_refine_diff_density_rms         0.146


_database_code_depnum_ccdc_archive 'CCDC 805819'
