# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_1
_database_code_depnum_ccdc_archive 'CCDC 1054759'
_audit_update_record             
;
2015-03-18 deposited with the CCDC.
2015-11-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H13 I N2 O3'
_chemical_formula_weight         384.16

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'
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                   8.046(6)
_cell_length_b                   9.777(7)
_cell_length_c                   10.002(7)
_cell_angle_alpha                112.309(11)
_cell_angle_beta                 91.342(11)
_cell_angle_gamma                95.164(12)
_cell_volume                     723.5(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.763
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376
_exptl_absorpt_coefficient_mu    2.221
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.5554
_exptl_absorpt_correction_T_max  0.6066
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3400
_diffrn_reflns_av_R_equivalents  0.0165
_diffrn_reflns_av_sigmaI/netI    0.0372
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         2.26
_diffrn_reflns_theta_max         24.68
_reflns_number_total             2355
_reflns_number_gt                2040
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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)+(0.1000P)²+6.2958P] 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         2355
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0467
_refine_ls_wR_factor_ref         0.1911
_refine_ls_wR_factor_gt          0.1318
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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 0.02042(8) 0.23467(8) -0.05951(7) 0.0574(3) Uani 1 1 d . . .
O1 O 0.3803(10) 0.4112(9) 0.0660(9) 0.064(2) Uani 1 1 d . . .
O2 O 0.1887(9) 0.1206(9) -0.5974(8) 0.0566(18) Uani 1 1 d . . .
O3 O 0.8545(10) 0.3313(8) 0.5415(8) 0.059(2) Uani 1 1 d . . .
N1 N 0.4389(9) 0.2960(8) -0.0256(7) 0.0361(15) Uani 1 1 d . . .
N2 N 0.5528(9) 0.2239(8) 0.0014(8) 0.0365(15) Uani 1 1 d . . .
C1 C 0.2039(10) 0.2206(9) -0.2115(9) 0.0337(17) Uani 1 1 d . . .
C2 C 0.1462(11) 0.1763(10) -0.3550(10) 0.0399(19) Uani 1 1 d . . .
H2A H 0.0320 0.1579 -0.3801 0.048 Uiso 1 1 calc R . .
C3 C 0.2591(12) 0.1596(9) -0.4600(9) 0.0386(19) Uani 1 1 d . . .
C4 C 0.4316(11) 0.1817(10) -0.4235(10) 0.0404(19) Uani 1 1 d . . .
H4A H 0.5075 0.1690 -0.4949 0.048 Uiso 1 1 calc R . .
C5 C 0.4878(12) 0.2223(10) -0.2814(10) 0.041(2) Uani 1 1 d . . .
H5A H 0.6018 0.2349 -0.2562 0.050 Uiso 1 1 calc R . .
C6 C 0.3721(11) 0.2445(8) -0.1753(9) 0.0352(18) Uani 1 1 d . . .
C7 C 0.2897(15) 0.1215(13) -0.7079(12) 0.060(3) Uani 1 1 d . . .
H7A H 0.2221 0.0936 -0.7964 0.090 Uiso 1 1 calc R . .
H7B H 0.3708 0.0521 -0.7202 0.090 Uiso 1 1 calc R . .
H7C H 0.3461 0.2195 -0.6834 0.090 Uiso 1 1 calc R . .
C8 C 0.6268(11) 0.2691(9) 0.1421(9) 0.0353(18) Uani 1 1 d . . .
C9 C 0.6303(13) 0.4084(10) 0.2594(10) 0.045(2) Uani 1 1 d . . .
H9A H 0.5794 0.4848 0.2468 0.054 Uiso 1 1 calc R . .
C10 C 0.7080(11) 0.4321(10) 0.3913(11) 0.045(2) Uani 1 1 d . . .
H10A H 0.7111 0.5251 0.4659 0.054 Uiso 1 1 calc R . .
C11 C 0.7816(11) 0.3205(10) 0.4152(10) 0.041(2) Uani 1 1 d . . .
C12 C 0.7848(12) 0.1832(10) 0.2976(10) 0.043(2) Uani 1 1 d . . .
H12A H 0.8391 0.1084 0.3101 0.052 Uiso 1 1 calc R . .
C13 C 0.7088(12) 0.1590(10) 0.1656(10) 0.043(2) Uani 1 1 d . . .
H13A H 0.7116 0.0675 0.0899 0.051 Uiso 1 1 calc R . .
C14 C 0.8572(15) 0.4687(12) 0.6636(11) 0.058(3) Uani 1 1 d . . .
H14A H 0.9132 0.4607 0.7457 0.088 Uiso 1 1 calc R . .
H14B H 0.7447 0.4906 0.6852 0.088 Uiso 1 1 calc R . .
H14C H 0.9156 0.5471 0.6418 0.088 Uiso 1 1 calc R . .


_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 2.119(8) . ?
O1 N1 1.289(10) . ?
O2 C3 1.373(11) . ?
O2 C7 1.389(13) . ?
O3 C11 1.342(11) . ?
O3 C14 1.430(13) . ?
N1 N2 1.288(10) . ?
N1 C6 1.458(11) . ?
N2 C8 1.403(11) . ?
C1 C6 1.369(12) . ?
C1 C2 1.387(12) . ?
C2 C3 1.377(13) . ?
C2 H2A 0.9300 . ?
C3 C4 1.403(13) . ?
C4 C5 1.375(13) . ?
C4 H4A 0.9300 . ?
C5 C6 1.395(13) . ?
C5 H5A 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 C13 1.401(12) . ?
C8 C9 1.418(13) . ?
C9 C10 1.374(13) . ?
C9 H9A 0.9300 . ?
C10 C11 1.381(13) . ?
C10 H10A 0.9300 . ?
C11 C12 1.412(13) . ?
C12 C13 1.368(13) . ?
C12 H12A 0.9300 . ?
C13 H13A 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 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
C3 O2 C7 119.5(8) . . ?
C11 O3 C14 118.5(8) . . ?
N2 N1 O1 126.5(7) . . ?
N2 N1 C6 116.9(6) . . ?
O1 N1 C6 116.6(7) . . ?
N1 N2 C8 120.3(7) . . ?
C6 C1 C2 120.0(7) . . ?
C6 C1 I1 123.3(6) . . ?
C2 C1 I1 116.6(6) . . ?
C3 C2 C1 119.6(8) . . ?
C3 C2 H2A 120.2 . . ?
C1 C2 H2A 120.2 . . ?
O2 C3 C2 114.8(8) . . ?
O2 C3 C4 124.7(8) . . ?
C2 C3 C4 120.5(8) . . ?
C5 C4 C3 119.5(8) . . ?
C5 C4 H4A 120.2 . . ?
C3 C4 H4A 120.2 . . ?
C4 C5 C6 119.4(8) . . ?
C4 C5 H5A 120.3 . . ?
C6 C5 H5A 120.3 . . ?
C1 C6 C5 120.9(8) . . ?
C1 C6 N1 122.1(8) . . ?
C5 C6 N1 117.0(8) . . ?
O2 C7 H7A 109.5 . . ?
O2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 N2 113.7(7) . . ?
C13 C8 C9 117.3(8) . . ?
N2 C8 C9 129.1(8) . . ?
C10 C9 C8 120.9(8) . . ?
C10 C9 H9A 119.6 . . ?
C8 C9 H9A 119.6 . . ?
C9 C10 C11 121.3(9) . . ?
C9 C10 H10A 119.3 . . ?
C11 C10 H10A 119.3 . . ?
O3 C11 C10 125.6(8) . . ?
O3 C11 C12 116.1(8) . . ?
C10 C11 C12 118.3(8) . . ?
C13 C12 C11 120.7(8) . . ?
C13 C12 H12A 119.6 . . ?
C11 C12 H12A 119.6 . . ?
C12 C13 C8 121.4(8) . . ?
C12 C13 H13A 119.3 . . ?
C8 C13 H13A 119.3 . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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
O1 N1 N2 C8 -0.3(13) . . . . ?
C6 N1 N2 C8 178.2(7) . . . . ?
C6 C1 C2 C3 -1.3(12) . . . . ?
I1 C1 C2 C3 -177.7(6) . . . . ?
C7 O2 C3 C2 170.9(9) . . . . ?
C7 O2 C3 C4 -9.3(14) . . . . ?
C1 C2 C3 O2 -177.7(8) . . . . ?
C1 C2 C3 C4 2.4(13) . . . . ?
O2 C3 C4 C5 179.3(8) . . . . ?
C2 C3 C4 C5 -0.9(13) . . . . ?
C3 C4 C5 C6 -1.6(12) . . . . ?
C2 C1 C6 C5 -1.2(12) . . . . ?
I1 C1 C6 C5 174.9(6) . . . . ?
C2 C1 C6 N1 177.9(7) . . . . ?
I1 C1 C6 N1 -6.0(11) . . . . ?
C4 C5 C6 C1 2.7(12) . . . . ?
C4 C5 C6 N1 -176.5(7) . . . . ?
N2 N1 C6 C1 130.9(8) . . . . ?
O1 N1 C6 C1 -50.4(11) . . . . ?
N2 N1 C6 C5 -49.9(10) . . . . ?
O1 N1 C6 C5 128.7(9) . . . . ?
N1 N2 C8 C13 161.9(8) . . . . ?
N1 N2 C8 C9 -18.8(14) . . . . ?
C13 C8 C9 C10 -1.5(14) . . . . ?
N2 C8 C9 C10 179.2(9) . . . . ?
C8 C9 C10 C11 -1.5(16) . . . . ?
C14 O3 C11 C10 0.3(15) . . . . ?
C14 O3 C11 C12 179.0(9) . . . . ?
C9 C10 C11 O3 -177.3(10) . . . . ?
C9 C10 C11 C12 4.0(15) . . . . ?
O3 C11 C12 C13 177.7(9) . . . . ?
C10 C11 C12 C13 -3.5(15) . . . . ?
C11 C12 C13 C8 0.5(15) . . . . ?
N2 C8 C13 C12 -178.6(9) . . . . ?
C9 C8 C13 C12 2.0(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.955
_diffrn_reflns_theta_full        24.68
_diffrn_measured_fraction_theta_full 0.955
_refine_diff_density_max         1.115
_refine_diff_density_min         -1.166
_refine_diff_density_rms         0.327
