# Electronic Supplementary Material (ESI) for RSC Advances
# This journal is © The Royal Society of Chemistry 2012


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#  experimental, refinement, atomic coordinates, 
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data_mb1124
_database_code_depnum_ccdc_archive 'CCDC 890138'
#TrackingRef '12364_web_deposit_cif_file_0_AndrewBond_1341302827.mb1124.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H10 I N O4'
_chemical_formula_sum            'C13 H10 I N O4'
_chemical_formula_weight         371.12

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                   7.6448(2)
_cell_length_b                   7.9573(2)
_cell_length_c                   11.2132(2)
_cell_angle_alpha                85.2820(10)
_cell_angle_beta                 81.1580(10)
_cell_angle_gamma                72.4990(10)
_cell_volume                     642.35(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5369
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      28.35

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.919
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             360
_exptl_absorpt_coefficient_mu    2.502
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.537
_exptl_absorpt_correction_T_max  0.885
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           ?

_diffrn_ambient_temperature      150(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 Nonius X8APEX-II CCD'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6830
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0233
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         3.51
_diffrn_reflns_theta_max         28.35
_diffrn_measured_fraction_theta_max 0.927
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.971
_reflns_number_total             2973
_reflns_number_gt                2821
_reflns_threshold_expression     I>2\s(I)

_computing_data_collection       'APEX2 v2010.1-2 (Bruker, 2010)'
_computing_cell_refinement       'SAINT v.7.68a (Bruker, 2010)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXTL v.6.12 (Sheldrick, 2008)'
_computing_structure_refinement  SHELXTL
_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^)+(0.0258P)^2^+0.4828P] 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         2973
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0223
_refine_ls_R_factor_gt           0.0207
_refine_ls_wR_factor_ref         0.0526
_refine_ls_wR_factor_gt          0.0516
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         1.523
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.077

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 -0.009096(17) 0.587529(18) 0.668744(12) 0.02513(6) Uani 1 1 d . . .
O1 O 0.6689(2) -0.0323(2) 0.19395(14) 0.0246(3) Uani 1 1 d . . .
O2 O 0.9305(2) -0.0730(2) 0.27812(16) 0.0324(4) Uani 1 1 d . . .
O3 O 0.2761(2) 0.63427(19) 0.82670(13) 0.0218(3) Uani 1 1 d . . .
O4 O 0.2945(4) 0.4357(3) 0.98166(18) 0.0575(7) Uani 1 1 d . . .
N1 N 0.4522(2) 0.1378(2) 0.33118(16) 0.0197(3) Uani 1 1 d . . .
C1 C 0.3684(3) 0.3438(3) 0.57217(18) 0.0179(4) Uani 1 1 d . . .
H1A H 0.3028 0.3150 0.5153 0.021 Uiso 1 1 calc R . .
C2 C 0.2748(3) 0.4620(3) 0.66154(18) 0.0183(4) Uani 1 1 d . . .
C3 C 0.3713(3) 0.5041(3) 0.74461(18) 0.0188(4) Uani 1 1 d . . .
C4 C 0.5591(3) 0.4295(3) 0.74061(19) 0.0217(4) Uani 1 1 d . . .
H4A H 0.6236 0.4586 0.7981 0.026 Uiso 1 1 calc R . .
C5 C 0.6537(3) 0.3111(3) 0.65169(19) 0.0212(4) Uani 1 1 d . . .
H5A H 0.7836 0.2591 0.6486 0.025 Uiso 1 1 calc R . .
C6 C 0.5602(3) 0.2673(2) 0.56649(18) 0.0182(4) Uani 1 1 d . . .
C7 C 0.6717(3) 0.1496(3) 0.47216(19) 0.0197(4) Uani 1 1 d . . .
H7A H 0.7983 0.1003 0.4825 0.024 Uiso 1 1 calc R . .
C8 C 0.6247(3) 0.0996(3) 0.37331(19) 0.0190(4) Uani 1 1 d . . .
C9 C 0.7665(3) -0.0106(3) 0.2837(2) 0.0231(4) Uani 1 1 d . . .
C10 C 0.4853(3) 0.0584(3) 0.23109(19) 0.0208(4) Uani 1 1 d . . .
C11 C 0.3544(3) 0.0496(3) 0.1497(2) 0.0276(5) Uani 1 1 d . . .
H11A H 0.2309 0.0671 0.1958 0.041 Uiso 1 1 calc R . .
H11B H 0.3955 -0.0661 0.1134 0.041 Uiso 1 1 calc R . .
H11C H 0.3497 0.1420 0.0858 0.041 Uiso 1 1 calc R . .
C12 C 0.2366(3) 0.5838(3) 0.9447(2) 0.0273(5) Uani 1 1 d . . .
C13 C 0.1139(4) 0.7378(3) 1.0138(2) 0.0344(6) Uani 1 1 d . . .
H13A H 0.1240 0.7146 1.1001 0.052 Uiso 1 1 calc R . .
H13B H -0.0146 0.7568 1.0008 0.052 Uiso 1 1 calc R . .
H13C H 0.1518 0.8433 0.9860 0.052 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 0.01552(8) 0.03123(9) 0.02702(9) -0.00989(6) 0.00023(5) -0.00363(5)
O1 0.0242(8) 0.0231(7) 0.0222(8) -0.0060(6) 0.0016(6) -0.0015(6)
O2 0.0204(8) 0.0350(9) 0.0349(9) -0.0100(7) 0.0006(7) 0.0024(6)
O3 0.0287(8) 0.0189(7) 0.0157(7) -0.0031(5) -0.0016(6) -0.0040(6)
O4 0.0925(18) 0.0317(10) 0.0285(10) 0.0067(8) 0.0129(11) -0.0007(11)
N1 0.0196(8) 0.0172(8) 0.0206(9) -0.0008(7) 0.0005(6) -0.0045(6)
C1 0.0190(9) 0.0185(9) 0.0170(9) -0.0021(7) -0.0022(7) -0.0064(7)
C2 0.0177(9) 0.0180(9) 0.0181(9) 0.0005(7) -0.0010(7) -0.0045(7)
C3 0.0244(10) 0.0164(9) 0.0155(9) -0.0004(7) -0.0006(7) -0.0066(7)
C4 0.0243(10) 0.0208(10) 0.0214(10) -0.0004(8) -0.0078(8) -0.0064(8)
C5 0.0192(10) 0.0205(10) 0.0232(10) 0.0017(8) -0.0045(8) -0.0045(7)
C6 0.0212(10) 0.0146(9) 0.0188(9) 0.0007(7) -0.0006(7) -0.0064(7)
C7 0.0170(9) 0.0169(9) 0.0230(10) 0.0001(8) 0.0000(7) -0.0029(7)
C8 0.0186(9) 0.0147(9) 0.0208(10) -0.0001(7) 0.0022(7) -0.0033(7)
C9 0.0240(10) 0.0206(10) 0.0218(10) -0.0030(8) 0.0006(8) -0.0037(8)
C10 0.0211(10) 0.0168(9) 0.0222(10) 0.0007(8) 0.0017(7) -0.0045(7)
C11 0.0301(12) 0.0278(11) 0.0245(11) -0.0047(9) -0.0043(9) -0.0067(9)
C12 0.0333(12) 0.0293(12) 0.0183(10) -0.0015(9) -0.0004(8) -0.0091(9)
C13 0.0417(14) 0.0355(13) 0.0219(11) -0.0082(10) 0.0014(10) -0.0058(10)

_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 C2 2.090(2) . ?
O1 C10 1.387(2) . ?
O1 C9 1.392(3) . ?
O2 C9 1.195(3) . ?
O3 C12 1.366(3) . ?
O3 C3 1.396(2) . ?
O4 C12 1.191(3) . ?
N1 C10 1.287(3) . ?
N1 C8 1.407(3) . ?
C1 C2 1.390(3) . ?
C1 C6 1.402(3) . ?
C1 H1A 0.9500 . ?
C2 C3 1.391(3) . ?
C3 C4 1.374(3) . ?
C4 C5 1.388(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.400(3) . ?
C5 H5A 0.9500 . ?
C6 C7 1.459(3) . ?
C7 C8 1.341(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.481(3) . ?
C10 C11 1.474(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 C13 1.492(3) . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

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
C10 O1 C9 105.57(16) . . ?
C12 O3 C3 118.40(16) . . ?
C10 N1 C8 105.48(17) . . ?
C2 C1 C6 119.60(19) . . ?
C2 C1 H1A 120.2 . . ?
C6 C1 H1A 120.2 . . ?
C1 C2 C3 120.04(18) . . ?
C1 C2 I1 120.87(15) . . ?
C3 C2 I1 119.03(14) . . ?
C4 C3 C2 121.04(19) . . ?
C4 C3 O3 120.19(19) . . ?
C2 C3 O3 118.59(18) . . ?
C3 C4 C5 119.3(2) . . ?
C3 C4 H4A 120.3 . . ?
C5 C4 H4A 120.3 . . ?
C4 C5 C6 120.83(19) . . ?
C4 C5 H5A 119.6 . . ?
C6 C5 H5A 119.6 . . ?
C5 C6 C1 119.19(18) . . ?
C5 C6 C7 117.23(18) . . ?
C1 C6 C7 123.51(19) . . ?
C8 C7 C6 130.5(2) . . ?
C8 C7 H7A 114.7 . . ?
C6 C7 H7A 114.7 . . ?
C7 C8 N1 131.09(19) . . ?
C7 C8 C9 120.96(19) . . ?
N1 C8 C9 107.92(18) . . ?
O2 C9 O1 122.15(19) . . ?
O2 C9 C8 133.0(2) . . ?
O1 C9 C8 104.85(17) . . ?
N1 C10 O1 116.17(19) . . ?
N1 C10 C11 128.88(19) . . ?
O1 C10 C11 114.95(18) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O4 C12 O3 122.3(2) . . ?
O4 C12 C13 127.6(2) . . ?
O3 C12 C13 110.07(19) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
C6 C1 C2 C3 0.1(3) . . . . ?
C6 C1 C2 I1 177.30(14) . . . . ?
C1 C2 C3 C4 -0.5(3) . . . . ?
I1 C2 C3 C4 -177.70(15) . . . . ?
C1 C2 C3 O3 174.62(17) . . . . ?
I1 C2 C3 O3 -2.6(2) . . . . ?
C12 O3 C3 C4 -77.6(3) . . . . ?
C12 O3 C3 C2 107.3(2) . . . . ?
C2 C3 C4 C5 0.4(3) . . . . ?
O3 C3 C4 C5 -174.61(18) . . . . ?
C3 C4 C5 C6 0.0(3) . . . . ?
C4 C5 C6 C1 -0.4(3) . . . . ?
C4 C5 C6 C7 176.65(19) . . . . ?
C2 C1 C6 C5 0.3(3) . . . . ?
C2 C1 C6 C7 -176.52(18) . . . . ?
C5 C6 C7 C8 -172.5(2) . . . . ?
C1 C6 C7 C8 4.4(3) . . . . ?
C6 C7 C8 N1 -3.2(4) . . . . ?
C6 C7 C8 C9 174.6(2) . . . . ?
C10 N1 C8 C7 179.1(2) . . . . ?
C10 N1 C8 C9 1.1(2) . . . . ?
C10 O1 C9 O2 -179.6(2) . . . . ?
C10 O1 C9 C8 -0.3(2) . . . . ?
C7 C8 C9 O2 0.5(4) . . . . ?
N1 C8 C9 O2 178.7(2) . . . . ?
C7 C8 C9 O1 -178.72(18) . . . . ?
N1 C8 C9 O1 -0.5(2) . . . . ?
C8 N1 C10 O1 -1.4(2) . . . . ?
C8 N1 C10 C11 178.3(2) . . . . ?
C9 O1 C10 N1 1.2(2) . . . . ?
C9 O1 C10 C11 -178.63(18) . . . . ?
C3 O3 C12 O4 6.9(4) . . . . ?
C3 O3 C12 C13 -172.5(2) . . . . ?