# 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_4ia_35dnba_mecn_11_rtrpt

# start Validation Reply Form
_vrf_PLAT431_4ia_35dnba_mecn_11_rtrpt 
;
PROBLEM: Short Inter HL..A  Contact I1     ..  O1      ..       2.99 Ang.  
RESPONSE: This is a halogen interaction.
;
# end Validation Reply Form


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H10 I N3 O6'
_chemical_formula_weight         431.14

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'
I I -0.4742 1.8119 '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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   P_21_21_21

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

_cell_length_a                   6.0536(7)
_cell_length_b                   10.5285(16)
_cell_length_c                   24.444(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1558.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.838
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    2.090
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8451
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10999
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.16
_diffrn_reflns_theta_max         27.47
_reflns_number_total             3552
_reflns_number_gt                3349
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2σ(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.

All H-atoms were placed in calculated positions and refined as riding on the 
atoms to which they were bonded with the exception of those involved in hydrogen
bonding. The anilinium group (NH3+) hydrogens H1A, H1B and H1C were identified 
using a Fourier difference synthesis and their positions and isotropic 
displacement parameters allowed to freely refine.

;

_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)+(0.0179P)²+0.2873P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_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   -0.016(15)
_refine_ls_number_reflns         3552
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0249
_refine_ls_R_factor_gt           0.0211
_refine_ls_wR_factor_ref         0.0505
_refine_ls_wR_factor_gt          0.0449
_refine_ls_goodness_of_fit_ref   1.154
_refine_ls_restrained_S_all      1.154
_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
C6 C 1.0255(4) 0.8402(3) 0.08495(11) 0.0209(6) Uani 1 1 d . . .
H6 H 1.1321 0.7920 0.1029 0.025 Uiso 1 1 calc R . .
H1A H 1.074(5) 1.199(3) 0.0516(11) 0.011(7) Uiso 1 1 d . . .
H1B H 0.828(5) 1.216(3) 0.0578(13) 0.027(9) Uiso 1 1 d . . .
H1C H 0.926(6) 1.192(3) 0.0004(14) 0.034(9) Uiso 1 1 d . . .
I1 I 0.76381(3) 0.592982(15) 0.085503(6) 0.02486(6) Uani 1 1 d . . .
O6 O 0.7399(4) 1.48091(17) 0.28292(7) 0.0265(4) Uani 1 1 d . . .
C9 C 0.2265(5) 1.3178(2) 0.27168(9) 0.0171(5) Uani 1 1 d . . .
H9 H 0.1757 1.3223 0.3075 0.021 Uiso 1 1 calc R . .
O4 O -0.1554(3) 1.1932(2) 0.29517(8) 0.0287(5) Uani 1 1 d . . .
O5 O 0.4885(3) 1.4438(2) 0.34419(8) 0.0272(5) Uani 1 1 d . . .
C4 C 0.9023(5) 1.0383(3) 0.04763(11) 0.0175(6) Uani 1 1 d . . .
O3 O -0.1957(3) 1.13126(18) 0.21112(7) 0.0225(4) Uani 1 1 d . . .
N2 N -0.0959(4) 1.1881(2) 0.24700(9) 0.0196(5) Uani 1 1 d . . .
C5 C 1.0614(5) 0.9679(3) 0.07444(11) 0.0194(6) Uani 1 1 d . . .
H5 H 1.1926 1.0061 0.0854 0.023 Uiso 1 1 calc R . .
O2 O 0.3494(3) 1.25200(19) 0.06847(7) 0.0208(4) Uani 1 1 d . . .
O1 O 0.6745(3) 1.31626(17) 0.10078(7) 0.0187(4) Uani 1 1 d . . .
C3 C 0.7064(5) 0.9836(3) 0.03042(11) 0.0211(6) Uani 1 1 d . . .
H3 H 0.6011 1.0318 0.0121 0.025 Uiso 1 1 calc R . .
C2 C 0.6691(5) 0.8555(3) 0.04085(11) 0.0227(6) Uani 1 1 d . . .
H2 H 0.5384 0.8174 0.0295 0.027 Uiso 1 1 calc R . .
N3 N 0.5579(4) 1.4381(2) 0.29773(10) 0.0197(5) Uani 1 1 d . . .
N1 N 0.9385(4) 1.1736(2) 0.03767(10) 0.0167(5) Uani 1 1 d . . .
C12 C 0.3795(4) 1.3039(3) 0.16340(11) 0.0156(5) Uani 1 1 d . . .
C13 C 0.4749(4) 1.2899(3) 0.10656(10) 0.0161(5) Uani 1 1 d . . .
C10 C 0.4240(4) 1.3737(2) 0.25568(11) 0.0159(5) Uani 1 1 d . . .
C7 C 0.1789(4) 1.2480(2) 0.17756(10) 0.0157(5) Uani 1 1 d . . .
H7 H 0.0934 1.2067 0.1514 0.019 Uiso 1 1 calc R . .
C11 C 0.5027(4) 1.3676(2) 0.20284(11) 0.0166(5) Uani 1 1 d . . .
H11 H 0.6363 1.4056 0.1937 0.020 Uiso 1 1 calc R . .
C1 C 0.8272(5) 0.7848(3) 0.06826(11) 0.0207(6) Uani 1 1 d . . .
C8 C 0.1103(4) 1.2554(2) 0.23144(11) 0.0164(5) Uani 1 1 d . . .

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
C6 0.0210(13) 0.0222(14) 0.0194(13) 0.0029(12) 0.0029(14) 0.0017(10)
I1 0.03286(10) 0.02003(9) 0.02170(9) 0.00004(7) 0.00467(10) -0.00607(9)
O6 0.0248(10) 0.0297(10) 0.0251(9) -0.0039(7) -0.0016(11) -0.0098(11)
C9 0.0204(13) 0.0183(12) 0.0127(10) 0.0005(8) 0.0013(12) 0.0034(12)
O4 0.0289(11) 0.0384(13) 0.0187(10) 0.0007(9) 0.0089(9) -0.0068(10)
O5 0.0280(11) 0.0381(13) 0.0156(10) -0.0032(9) -0.0007(9) -0.0028(9)
C4 0.0217(14) 0.0165(13) 0.0144(13) 0.0005(11) 0.0024(11) 0.0001(11)
O3 0.0191(10) 0.0251(10) 0.0232(9) -0.0007(8) -0.0028(8) -0.0052(8)
N2 0.0163(11) 0.0192(12) 0.0233(12) 0.0037(10) 0.0028(10) 0.0017(9)
C5 0.0180(13) 0.0240(14) 0.0162(13) 0.0002(11) -0.0027(11) -0.0032(11)
O2 0.0212(9) 0.0271(11) 0.0142(9) -0.0001(8) 0.0009(8) -0.0044(8)
O1 0.0165(9) 0.0196(9) 0.0199(9) -0.0017(7) 0.0028(7) -0.0030(7)
C3 0.0193(15) 0.0247(14) 0.0192(12) 0.0019(10) -0.0042(12) 0.0012(12)
C2 0.0186(13) 0.0271(15) 0.0225(14) -0.0043(12) 0.0016(12) -0.0057(11)
N3 0.0198(11) 0.0180(13) 0.0213(12) -0.0013(9) -0.0023(10) -0.0011(9)
N1 0.0162(12) 0.0193(12) 0.0147(11) 0.0001(9) 0.0009(10) 0.0000(9)
C12 0.0183(13) 0.0139(13) 0.0146(12) 0.0011(10) 0.0009(11) 0.0003(10)
C13 0.0203(13) 0.0127(13) 0.0153(12) 0.0028(10) 0.0013(11) -0.0001(10)
C10 0.0152(12) 0.0158(13) 0.0166(12) -0.0014(10) -0.0030(11) 0.0015(9)
C7 0.0176(12) 0.0155(13) 0.0140(12) 0.0001(10) -0.0020(10) 0.0018(10)
C11 0.0147(12) 0.0148(13) 0.0203(13) 0.0018(11) 0.0002(11) 0.0002(10)
C1 0.0267(14) 0.0190(13) 0.0164(12) -0.0014(11) 0.0062(11) -0.0015(11)
C8 0.0129(12) 0.0158(13) 0.0204(13) 0.0025(10) 0.0012(11) -0.0001(10)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
C6 C5 1.387(4) . ?
C6 C1 1.395(4) . ?
I1 C1 2.098(3) . ?
O6 N3 1.244(3) . ?
C9 C8 1.376(4) . ?
C9 C10 1.389(4) . ?
O4 N2 1.232(3) . ?
O5 N3 1.212(3) . ?
C4 C5 1.381(4) . ?
C4 C3 1.384(4) . ?
C4 N1 1.462(4) . ?
O3 N2 1.222(3) . ?
N2 C8 1.485(3) . ?
O2 C13 1.266(3) . ?
O1 C13 1.248(3) . ?
C3 C2 1.391(4) . ?
C2 C1 1.385(4) . ?
N3 C10 1.474(3) . ?
C12 C11 1.391(4) . ?
C12 C7 1.393(4) . ?
C12 C13 1.512(4) . ?
C10 C11 1.378(4) . ?
C7 C8 1.383(3) . ?

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
C5 C6 C1 119.1(3) . . ?
C8 C9 C10 116.2(2) . . ?
C5 C4 C3 121.2(3) . . ?
C5 C4 N1 119.9(3) . . ?
C3 C4 N1 118.9(3) . . ?
O3 N2 O4 124.2(2) . . ?
O3 N2 C8 117.7(2) . . ?
O4 N2 C8 118.0(2) . . ?
C4 C5 C6 120.0(3) . . ?
C4 C3 C2 119.1(3) . . ?
C1 C2 C3 119.9(3) . . ?
O5 N3 O6 124.2(2) . . ?
O5 N3 C10 119.0(2) . . ?
O6 N3 C10 116.8(2) . . ?
C11 C12 C7 119.9(2) . . ?
C11 C12 C13 118.6(2) . . ?
C7 C12 C13 121.3(2) . . ?
O1 C13 O2 124.6(2) . . ?
O1 C13 C12 116.9(2) . . ?
O2 C13 C12 118.5(2) . . ?
C11 C10 C9 122.8(2) . . ?
C11 C10 N3 119.0(2) . . ?
C9 C10 N3 118.2(2) . . ?
C8 C7 C12 118.3(2) . . ?
C10 C11 C12 119.1(2) . . ?
C2 C1 C6 120.7(3) . . ?
C2 C1 I1 119.2(2) . . ?
C6 C1 I1 120.0(2) . . ?
C9 C8 C7 123.6(2) . . ?
C9 C8 N2 118.3(2) . . ?
C7 C8 N2 118.0(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
N1 H1B O1 0.94(3) 1.75(3) 2.681(3) 167(3) .
N1 H1A O2 0.93(3) 1.80(3) 2.727(3) 172(2) 1_655
N1 H1C O2 0.94(3) 1.84(3) 2.763(3) 168(3) 3_575

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.560
_refine_diff_density_min         -0.357
_refine_diff_density_rms         0.086
_database_code_depnum_ccdc_archive 'CCDC 984155'
#######################################################################
#
#                 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_copy_4ia_35dnba_meoh_rtrpt

# start Validation Reply Form
_vrf_PLAT201_copy_4ia_35dnba_meoh_rtrpt 
;
PROBLEM: Isotropic non-H Atoms in Main Residue(s) .......         24 Why ? 
RESPONSE: Overlap of two disordered positions means the atoms are too 
close together to allow anisotropic refinement. The atoms are therefore 
refined isotropically.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H24 I2 N6 O13'
_chemical_formula_weight         894.32

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'
I I -0.4742 1.8119 '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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   9.947(7)
_cell_length_b                   12.823(9)
_cell_length_c                   13.020(10)
_cell_angle_alpha                94.249(16)
_cell_angle_beta                 91.739(16)
_cell_angle_gamma                90.493(19)
_cell_volume                     1655(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.730
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    1.967
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.6538
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            38785
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_av_sigmaI/netI    0.0460
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         27.48
_reflns_number_total             7522
_reflns_number_gt                4315
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2σ(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.

There is a significant amount of crystallographic disorder in this molecular
complex.  This means that it is not possible to accurately assign the 
protonation states of the molecules and therefore assign hydrogen atoms to 
the carboxyl and amine groups.  The hydrogen atoms for these were therefore
omitted from the model but the chemical formula given includes the missing
H atoms.

The two 4-iodoaniline molecules are well-described and the positions and 
anisotropic displacement parameters for all heavy atoms were allowed to 
refine freely. The aromatic hydrogen atoms of the 4-iodoaniline molecules 
were placed in calculated positions and refined as riding on the atoms to 
which they were bonded. The hydrogen atoms on the amine group could not be 
determined due to the ambiguity of the protonation state of this molecule.  
There is a statistical disorder between an NH2 and NH3+ group. 

The two independent 3,5-dinitrobenzoic acid molecules showed significant
elongation of the anisotropic displacement parameters when the positions
and adps were allowed to refine freely.  One of the nitro groups for both
molecules showed bond lengths and angles which were characteristic of a 
well-described nitro group.  However, the C-N or C-C distances and N-O
or C-O distances of the second nitro or carboxylic acid groups, 
respectively took values in between those expected for the two groups. A 
model was therefore adopted where the molecules could adopt two positions
around the pivot nitro group but with the carboxylic acid or nitro groups
flipped.  Due to the close positions of these two orientations, significant
constraints had to be applied for a chemically meaningful refinement.  The
benzene rings were constrained using the AFIX 66 command.  The C-C distances
of the carboxylic acid groups were constrained to take a standard value of 
1.51 Angstroms using a DFIX command.  The C-N distances of the disordered
nitro groups were constrained to take a value of 1.47 Angstroms.  The N-O 
distances were constrained to take values of 1.22 Angstroms.  The C-O 
distances of the carboxylic acid groups were not restrained due to the 
ambiguity about the protonation state.  These groups are 50:50 disordered
between a carboxylic acid group and a carboxylate group.  Pairs of C/N/O
(A and B) atoms for the whole molecule were constrained to be equal using 
the EADP command to ensure sensible adps were obtained; all atoms except
the pivot nitro group were refined only isotropically.  The occupancies
of the two positions for each molecule were allowed to freely refine and
these converged at approximately 50:50. The aromatic hydrogen atoms of the
3,5-dinitrobenzoic acid molecules were placed in calculated positions and 
refined as riding on the atoms to which they were bonded.

The methanol molecule was also found to be disordered over two positions.
The two positions were allowed to freely refine to approximately 50:50.
The close positions of the two meant that these atoms were only refined
isotropically.  The hydrogen atoms of the methyl groups were placed on
calculated positions; it was not possible to identify the hydrogen atoms
of the hydroxyl group in a Fourier difference map due to the disorder.

;

_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)+(0.0777P)²+4.0012P] 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         7522
_refine_ls_number_parameters     344
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.1317
_refine_ls_R_factor_gt           0.0791
_refine_ls_wR_factor_ref         0.2125
_refine_ls_wR_factor_gt          0.1856
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_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
O5A O 0.0402(18) 0.5426(10) 0.1159(10) 0.103(4) Uiso 0.538(16) 1 d PD A 1
N7A N 0.0286(17) 0.4470(10) 0.1168(12) 0.084(5) Uiso 0.538(16) 1 d PD A 1
O4A O 0.5342(15) 0.5293(10) 0.1164(9) 0.087(4) Uiso 0.538(16) 1 d P A 1
C101 C 0.537(2) 0.4332(16) 0.1137(16) 0.079(5) Uiso 0.538(16) 1 d PD A 1
O3A O 0.6281(18) 0.3717(14) 0.1010(13) 0.119(4) Uiso 0.538(16) 1 d P A 1
O6A O -0.082(2) 0.4003(17) 0.1118(16) 0.124(4) Uiso 0.538(16) 1 d PD A 1
N4A N 0.2548(9) 0.1156(5) 0.1558(5) 0.0827(19) Uani 0.538(16) 1 d PD A 1
O1A O 0.1487(8) 0.0706(5) 0.1592(5) 0.106(2) Uani 0.538(16) 1 d P A 1
O2A O 0.3655(8) 0.0738(5) 0.1640(6) 0.112(2) Uani 0.538(16) 1 d P A 1
C19A C 0.2699(12) 0.2264(5) 0.1398(11) 0.065(2) Uiso 0.538(16) 1 d PGD A 1
C20A C 0.3932(10) 0.2767(7) 0.1320(10) 0.066(2) Uiso 0.538(16) 1 d PG A 1
H20A H 0.4724 0.2389 0.1351 0.079 Uiso 0.538(16) 1 calc PR A 1
C21A C 0.3980(11) 0.3834(7) 0.1196(9) 0.068(2) Uiso 0.538(16) 1 d PGD A 1
C22A C 0.2795(13) 0.4398(5) 0.1149(9) 0.061(2) Uiso 0.538(16) 1 d PG A 1
H22A H 0.2827 0.5112 0.1066 0.074 Uiso 0.538(16) 1 calc PR A 1
C23A C 0.1563(11) 0.3895(7) 0.1227(9) 0.065(2) Uiso 0.538(16) 1 d PGD A 1
C24A C 0.1515(10) 0.2828(7) 0.1351(11) 0.066(2) Uiso 0.538(16) 1 d PG A 1
H24A H 0.0690 0.2492 0.1403 0.079 Uiso 0.538(16) 1 calc PR A 1
O5B O -0.0302(17) 0.5286(10) 0.1121(10) 0.079(4) Uiso 0.462(16) 1 d P A 2
C100 C -0.029(2) 0.4336(17) 0.1132(16) 0.069(5) Uiso 0.462(16) 1 d PD A 2
O4B O 0.4617(18) 0.5477(10) 0.1098(10) 0.090(4) Uiso 0.462(16) 1 d PD A 2
N21B N 0.4771(18) 0.4520(11) 0.1152(12) 0.077(5) Uiso 0.462(16) 1 d PD A 2
O3B O 0.588(2) 0.4087(19) 0.1144(18) 0.119(4) Uiso 0.462(16) 1 d PD A 2
O6B O -0.126(2) 0.3681(17) 0.1015(17) 0.124(4) Uiso 0.462(16) 1 d P A 2
N4B N 0.2548(9) 0.1156(5) 0.1558(5) 0.0827(19) Uani 0.462(16) 1 d PD A 2
O1B O 0.1487(8) 0.0706(5) 0.1592(5) 0.106(2) Uani 0.462(16) 1 d P A 2
O2B O 0.3655(8) 0.0738(5) 0.1640(6) 0.112(2) Uani 0.462(16) 1 d P A 2
C19B C 0.2389(13) 0.2268(6) 0.1402(13) 0.065(2) Uiso 0.462(16) 1 d PGD A 2
C20B C 0.3565(12) 0.2853(8) 0.1355(12) 0.066(2) Uiso 0.462(16) 1 d PG A 2
H20B H 0.4396 0.2533 0.1416 0.079 Uiso 0.462(16) 1 calc PR A 2
C21B C 0.3500(13) 0.3916(8) 0.1217(11) 0.068(2) Uiso 0.462(16) 1 d PGD A 2
C22B C 0.2257(15) 0.4394(6) 0.1125(10) 0.061(2) Uiso 0.462(16) 1 d PG A 2
H22B H 0.2214 0.5105 0.1033 0.074 Uiso 0.462(16) 1 calc PR A 2
C23B C 0.1081(13) 0.3809(8) 0.1172(11) 0.065(2) Uiso 0.462(16) 1 d PGD A 2
C24B C 0.1146(12) 0.2746(8) 0.1311(12) 0.066(2) Uiso 0.462(16) 1 d PG A 2
H24B H 0.0359 0.2355 0.1342 0.079 Uiso 0.462(16) 1 calc PR A 2
N5A N 0.9964(15) 0.1731(10) 0.3774(11) 0.074(3) Uiso 0.541(16) 1 d PD B 3
O11A O 0.9860(17) 0.2688(10) 0.3694(11) 0.101(3) Uiso 0.541(16) 1 d PD B 3
O12A O 1.1084(18) 0.1286(15) 0.3797(15) 0.105(3) Uiso 0.541(16) 1 d PD B 3
C201 C 0.4886(18) 0.1561(13) 0.3817(13) 0.065(2) Uiso 0.541(16) 1 d PD B 3
O7A O 0.4860(17) 0.2528(10) 0.3789(10) 0.094(3) Uiso 0.541(16) 1 d P B 3
O8A O 0.3969(16) 0.0959(12) 0.3895(12) 0.098(3) Uiso 0.541(16) 1 d P B 3
N6A N 0.7753(8) -0.1626(4) 0.3882(5) 0.0735(17) Uani 0.541(16) 1 d PD B 3
O9A O 0.6687(7) -0.2079(4) 0.3898(5) 0.0940(18) Uani 0.541(16) 1 d P B 3
O10A O 0.8837(7) -0.2051(4) 0.3871(5) 0.103(2) Uani 0.541(16) 1 d P B 3
C13A C 0.7582(11) -0.0525(5) 0.3843(11) 0.059(2) Uiso 0.541(16) 1 d PGD B 3
C14A C 0.8760(9) 0.0062(7) 0.3818(10) 0.061(2) Uiso 0.541(16) 1 d PG B 3
H14A H 0.9589 -0.0269 0.3816 0.073 Uiso 0.541(16) 1 calc PR B 3
C15A C 0.8700(10) 0.1142(6) 0.3796(9) 0.059(2) Uiso 0.541(16) 1 d PGD B 3
C16A C 0.7461(12) 0.1636(5) 0.3799(9) 0.059(2) Uiso 0.541(16) 1 d PG B 3
H16A H 0.7421 0.2359 0.3785 0.070 Uiso 0.541(16) 1 calc PR B 3
C17A C 0.6283(10) 0.1049(7) 0.3824(9) 0.056(2) Uiso 0.541(16) 1 d PGD B 3
C18A C 0.6343(10) -0.0031(7) 0.3846(10) 0.0581(19) Uiso 0.541(16) 1 d PG B 3
H18A H 0.5555 -0.0424 0.3863 0.070 Uiso 0.541(16) 1 calc PR B 3
C200 C 1.049(2) 0.1697(17) 0.3794(17) 0.074(3) Uiso 0.459(16) 1 d PD B 4
O11B O 1.044(2) 0.2632(14) 0.3678(13) 0.101(3) Uiso 0.459(16) 1 d P B 4
O12B O 1.145(2) 0.1156(17) 0.3950(16) 0.105(3) Uiso 0.459(16) 1 d P B 4
N20B N 0.5426(17) 0.1701(10) 0.3877(11) 0.065(2) Uiso 0.459(16) 1 d PD B 4
O7B O 0.545(2) 0.2650(11) 0.3747(12) 0.094(3) Uiso 0.459(16) 1 d PD B 4
O8B O 0.4347(19) 0.1252(16) 0.4053(15) 0.098(3) Uiso 0.459(16) 1 d PD B 4
N6B N 0.7753(8) -0.1626(4) 0.3882(5) 0.0735(17) Uani 0.459(16) 1 d PD B 4
O9B O 0.6687(7) -0.2079(4) 0.3898(5) 0.0940(18) Uani 0.459(16) 1 d P B 4
O10B O 0.8837(7) -0.2051(4) 0.3871(5) 0.103(2) Uani 0.459(16) 1 d P B 4
C13B C 0.7873(13) -0.0468(6) 0.3860(13) 0.059(2) Uiso 0.459(16) 1 d PGD B 4
C14B C 0.9098(12) 0.0058(8) 0.3839(12) 0.061(2) Uiso 0.459(16) 1 d PG B 4
H14B H 0.9896 -0.0315 0.3830 0.073 Uiso 0.459(16) 1 calc PR B 4
C15B C 0.9132(12) 0.1141(8) 0.3832(11) 0.059(2) Uiso 0.459(16) 1 d PGD B 4
C16B C 0.7940(14) 0.1699(6) 0.3846(10) 0.059(2) Uiso 0.459(16) 1 d PG B 4
H16B H 0.7962 0.2424 0.3841 0.070 Uiso 0.459(16) 1 calc PR B 4
C17B C 0.6714(12) 0.1173(8) 0.3867(10) 0.056(2) Uiso 0.459(16) 1 d PGD B 4
C18B C 0.6680(11) 0.0090(8) 0.3874(11) 0.0581(19) Uiso 0.459(16) 1 d PG B 4
H18B H 0.5860 -0.0262 0.3888 0.070 Uiso 0.459(16) 1 calc PR B 4
O15A O 0.278(2) 0.4402(8) 0.6440(8) 0.069(4) Uiso 0.50(3) 1 d P C 5
C50A C 0.239(2) 0.5447(15) 0.639(2) 0.073(6) Uiso 0.50(3) 1 d P C 5
H50A H 0.1430 0.5491 0.6434 0.109 Uiso 0.50(3) 1 calc PR C 5
H50B H 0.2669 0.5700 0.5758 0.109 Uiso 0.50(3) 1 calc PR C 5
H50C H 0.2806 0.5864 0.6962 0.109 Uiso 0.50(3) 1 calc PR C 5
O15B O 0.209(2) 0.4373(8) 0.6410(7) 0.064(4) Uiso 0.50(3) 1 d P C 6
C50B C 0.239(2) 0.5469(16) 0.676(2) 0.081(6) Uiso 0.50(3) 1 d P C 6
H50D H 0.2588 0.5522 0.7486 0.121 Uiso 0.50(3) 1 calc PR C 6
H50E H 0.1619 0.5892 0.6616 0.121 Uiso 0.50(3) 1 calc PR C 6
H50F H 0.3145 0.5710 0.6401 0.121 Uiso 0.50(3) 1 calc PR C 6
N8 N 1.2642(6) 0.3747(4) 0.4326(5) 0.0734(17) Uani 1 1 d . . .
I1 I 0.75208(7) 1.12113(4) 0.07349(5) 0.0934(3) Uani 1 1 d . . .
N1 N 0.7584(7) 0.6434(5) 0.1651(5) 0.0728(16) Uani 1 1 d . . .
C1 C 0.7528(9) 0.9613(6) 0.1009(6) 0.0711(19) Uani 1 1 d . . .
C4 C 0.7567(7) 0.7527(5) 0.1406(5) 0.0596(16) Uani 1 1 d . . .
C5 C 0.8765(8) 0.8056(6) 0.1309(6) 0.0702(19) Uani 1 1 d . . .
H5 H 0.9578 0.7712 0.1383 0.084 Uiso 1 1 calc R . .
C3 C 0.6363(8) 0.8045(6) 0.1315(6) 0.0682(18) Uani 1 1 d . . .
H3 H 0.5556 0.7695 0.1397 0.082 Uiso 1 1 calc R . .
C6 C 0.8752(8) 0.9102(6) 0.1099(6) 0.0719(19) Uani 1 1 d . . .
H6 H 0.9555 0.9459 0.1018 0.086 Uiso 1 1 calc R . .
C2 C 0.6359(8) 0.9088(6) 0.1099(6) 0.0718(19) Uani 1 1 d . . .
H2 H 0.5546 0.9429 0.1016 0.086 Uiso 1 1 calc R . .
I2 I 1.26642(7) 0.83516(5) 0.28872(6) 0.1027(3) Uani 1 1 d . . .
C10 C 1.2652(7) 0.4781(5) 0.3953(5) 0.0601(16) Uani 1 1 d . . .
C7 C 1.2655(8) 0.6809(6) 0.3350(6) 0.0681(18) Uani 1 1 d . . .
C9 C 1.1468(8) 0.5310(6) 0.3798(6) 0.074(2) Uani 1 1 d . . .
H9 H 1.0652 0.4978 0.3900 0.089 Uiso 1 1 calc R . .
C8 C 1.1466(8) 0.6314(6) 0.3499(6) 0.076(2) Uani 1 1 d . . .
H8 H 1.0657 0.6655 0.3398 0.092 Uiso 1 1 calc R . .
C11 C 1.3855(7) 0.5282(6) 0.3794(6) 0.0691(19) Uani 1 1 d . . .
H11 H 1.4662 0.4936 0.3888 0.083 Uiso 1 1 calc R . .
C12 C 1.3865(7) 0.6302(6) 0.3493(6) 0.073(2) Uani 1 1 d . . .
H12 H 1.4675 0.6640 0.3390 0.088 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
N4A 0.105(6) 0.072(4) 0.071(4) 0.007(3) 0.002(4) 0.005(4)
O1A 0.115(5) 0.078(4) 0.126(5) 0.016(4) 0.008(4) -0.021(4)
O2A 0.122(6) 0.081(4) 0.136(6) 0.021(4) 0.007(4) 0.023(4)
N4B 0.105(6) 0.072(4) 0.071(4) 0.007(3) 0.002(4) 0.005(4)
O1B 0.115(5) 0.078(4) 0.126(5) 0.016(4) 0.008(4) -0.021(4)
O2B 0.122(6) 0.081(4) 0.136(6) 0.021(4) 0.007(4) 0.023(4)
N6A 0.097(5) 0.050(3) 0.074(4) 0.003(3) -0.001(4) 0.009(4)
O9A 0.111(5) 0.054(3) 0.118(5) 0.008(3) 0.005(4) -0.008(3)
O10A 0.116(5) 0.058(3) 0.135(6) 0.008(3) 0.008(4) 0.029(3)
N6B 0.097(5) 0.050(3) 0.074(4) 0.003(3) -0.001(4) 0.009(4)
O9B 0.111(5) 0.054(3) 0.118(5) 0.008(3) 0.005(4) -0.008(3)
O10B 0.116(5) 0.058(3) 0.135(6) 0.008(3) 0.008(4) 0.029(3)
N8 0.071(4) 0.047(3) 0.103(5) 0.010(3) -0.001(3) 0.007(3)
I1 0.1189(6) 0.0609(3) 0.1022(5) 0.0184(3) 0.0041(4) 0.0025(3)
N1 0.078(4) 0.058(3) 0.082(4) 0.009(3) 0.000(3) 0.000(3)
C1 0.085(6) 0.065(4) 0.064(4) 0.006(3) 0.002(4) 0.003(4)
C4 0.069(5) 0.051(4) 0.060(4) 0.004(3) 0.004(3) 0.001(3)
C5 0.067(5) 0.068(5) 0.077(5) 0.009(4) 0.004(4) 0.011(4)
C3 0.058(4) 0.074(5) 0.073(5) 0.010(4) 0.005(3) 0.002(4)
C6 0.063(5) 0.072(5) 0.082(5) 0.007(4) 0.005(4) -0.004(4)
C2 0.066(5) 0.070(5) 0.080(5) 0.010(4) 0.000(4) 0.006(4)
I2 0.1026(5) 0.0697(4) 0.1410(6) 0.0411(4) 0.0073(4) 0.0053(3)
C10 0.057(4) 0.051(4) 0.071(4) 0.003(3) -0.002(3) 0.000(3)
C7 0.071(5) 0.064(4) 0.071(5) 0.011(3) 0.003(4) -0.001(4)
C9 0.060(5) 0.061(4) 0.103(6) 0.018(4) 0.002(4) 0.000(3)
C8 0.062(5) 0.081(5) 0.087(5) 0.016(4) -0.001(4) 0.021(4)
C11 0.051(4) 0.065(4) 0.092(5) 0.014(4) 0.003(4) 0.010(3)
C12 0.053(4) 0.074(5) 0.094(6) 0.014(4) 0.006(4) 0.001(4)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
O5A N7A 1.231(13) . ?
N7A O6A 1.246(16) . ?
N7A C23A 1.477(13) . ?
O4A C101 1.23(2) . ?
C101 O3A 1.21(2) . ?
C101 C21A 1.524(16) . ?
N4A O1A 1.202(9) . ?
N4A O2A 1.234(9) . ?
N4A C19A 1.458(9) . ?
C19A C20A 1.3900 . ?
C19A C24A 1.3900 . ?
C20A C21A 1.3900 . ?
C21A C22A 1.3900 . ?
C22A C23A 1.3900 . ?
C23A C24A 1.3900 . ?
O5B C100 1.22(2) . ?
C100 O6B 1.27(3) . ?
C100 C23B 1.528(16) . ?
O4B N21B 1.244(14) . ?
N21B O3B 1.239(17) . ?
N21B C21B 1.485(14) . ?
C19B C20B 1.3900 . ?
C19B C24B 1.3900 . ?
C20B C21B 1.3900 . ?
C21B C22B 1.3900 . ?
C22B C23B 1.3900 . ?
C23B C24B 1.3900 . ?
N5A O11A 1.244(14) . ?
N5A O12A 1.258(15) . ?
N5A C15A 1.463(12) . ?
C201 O8A 1.20(2) . ?
C201 O7A 1.245(18) . ?
C201 C17A 1.542(14) . ?
N6A O9A 1.206(9) . ?
N6A O10A 1.212(9) . ?
N6A C13A 1.428(8) . ?
C13A C14A 1.3900 . ?
C13A C18A 1.3900 . ?
C14A C15A 1.3900 . ?
C15A C16A 1.3900 . ?
C16A C17A 1.3900 . ?
C17A C18A 1.3900 . ?
C200 O12B 1.21(3) . ?
C200 O11B 1.22(2) . ?
C200 C15B 1.525(16) . ?
N20B O7B 1.242(14) . ?
N20B O8B 1.249(16) . ?
N20B C17B 1.454(13) . ?
C13B C14B 1.3900 . ?
C13B C18B 1.3900 . ?
C14B C15B 1.3900 . ?
C15B C16B 1.3900 . ?
C16B C17B 1.3900 . ?
C17B C18B 1.3900 . ?
O15A C50A 1.40(2) . ?
O15B C50B 1.47(2) . ?
N8 C10 1.445(8) . ?
I1 C1 2.106(8) . ?
N1 C4 1.461(9) . ?
C1 C2 1.351(11) . ?
C1 C6 1.394(11) . ?
C4 C5 1.380(10) . ?
C4 C3 1.380(10) . ?
C5 C6 1.389(10) . ?
C3 C2 1.386(10) . ?
I2 C7 2.110(7) . ?
C10 C9 1.382(10) . ?
C10 C11 1.382(10) . ?
C7 C8 1.363(11) . ?
C7 C12 1.387(10) . ?
C9 C8 1.373(10) . ?
C11 C12 1.393(10) . ?

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
O5A N7A O6A 123.4(16) . . ?
O5A N7A C23A 115.3(13) . . ?
O6A N7A C23A 121.3(14) . . ?
O3A C101 O4A 131.8(17) . . ?
O3A C101 C21A 114.9(15) . . ?
O4A C101 C21A 113.1(17) . . ?
O1A N4A O2A 124.4(7) . . ?
O1A N4A C19A 124.6(9) . . ?
O2A N4A C19A 111.0(8) . . ?
C20A C19A C24A 120.0 . . ?
C20A C19A N4A 124.0(7) . . ?
C24A C19A N4A 116.0(7) . . ?
C21A C20A C19A 120.0 . . ?
C20A C21A C22A 120.0 . . ?
C20A C21A C101 116.9(10) . . ?
C22A C21A C101 123.1(10) . . ?
C23A C22A C21A 120.0 . . ?
C22A C23A C24A 120.0 . . ?
C22A C23A N7A 121.3(8) . . ?
C24A C23A N7A 118.7(8) . . ?
C23A C24A C19A 120.0 . . ?
O5B C100 O6B 129.6(18) . . ?
O5B C100 C23B 117.4(19) . . ?
O6B C100 C23B 112.6(16) . . ?
O3B N21B O4B 124.0(17) . . ?
O3B N21B C21B 121.5(15) . . ?
O4B N21B C21B 114.5(14) . . ?
C20B C19B C24B 120.0 . . ?
C19B C20B C21B 120.0 . . ?
C22B C21B C20B 120.0 . . ?
C22B C21B N21B 121.0(9) . . ?
C20B C21B N21B 119.0(9) . . ?
C21B C22B C23B 120.0 . . ?
C24B C23B C22B 120.0 . . ?
C24B C23B C100 119.4(11) . . ?
C22B C23B C100 120.6(11) . . ?
C23B C24B C19B 120.0 . . ?
O11A N5A O12A 122.3(14) . . ?
O11A N5A C15A 116.0(11) . . ?
O12A N5A C15A 121.6(13) . . ?
O8A C201 O7A 129.0(14) . . ?
O8A C201 C17A 114.1(13) . . ?
O7A C201 C17A 116.8(14) . . ?
O9A N6A O10A 124.5(7) . . ?
O9A N6A C13A 111.6(7) . . ?
O10A N6A C13A 123.9(8) . . ?
C14A C13A C18A 120.0 . . ?
C14A C13A N6A 115.6(7) . . ?
C18A C13A N6A 124.4(7) . . ?
C13A C14A C15A 120.0 . . ?
C16A C15A C14A 120.0 . . ?
C16A C15A N5A 121.7(7) . . ?
C14A C15A N5A 118.3(7) . . ?
C17A C16A C15A 120.0 . . ?
C16A C17A C18A 120.0 . . ?
C16A C17A C201 121.9(8) . . ?
C18A C17A C201 118.1(8) . . ?
C17A C18A C13A 120.0 . . ?
O12B C200 O11B 129.6(18) . . ?
O12B C200 C15B 114.6(18) . . ?
O11B C200 C15B 115.6(18) . . ?
O7B N20B O8B 120.4(15) . . ?
O7B N20B C17B 116.6(12) . . ?
O8B N20B C17B 123.0(13) . . ?
C14B C13B C18B 120.0 . . ?
C13B C14B C15B 120.0 . . ?
C16B C15B C14B 120.0 . . ?
C16B C15B C200 121.1(11) . . ?
C14B C15B C200 118.9(11) . . ?
C15B C16B C17B 120.0 . . ?
C18B C17B C16B 120.0 . . ?
C18B C17B N20B 116.8(8) . . ?
C16B C17B N20B 123.2(8) . . ?
C17B C18B C13B 120.0 . . ?
C2 C1 C6 120.3(7) . . ?
C2 C1 I1 120.4(6) . . ?
C6 C1 I1 119.3(6) . . ?
C5 C4 C3 119.9(7) . . ?
C5 C4 N1 119.6(6) . . ?
C3 C4 N1 120.4(6) . . ?
C4 C5 C6 119.8(7) . . ?
C4 C3 C2 120.0(7) . . ?
C5 C6 C1 119.6(7) . . ?
C1 C2 C3 120.5(7) . . ?
C9 C10 C11 118.5(6) . . ?
C9 C10 N8 120.9(6) . . ?
C11 C10 N8 120.4(6) . . ?
C8 C7 C12 120.4(7) . . ?
C8 C7 I2 120.1(6) . . ?
C12 C7 I2 119.5(6) . . ?
C8 C9 C10 121.6(7) . . ?
C7 C8 C9 119.8(7) . . ?
C10 C11 C12 120.4(6) . . ?
C7 C12 C11 119.4(7) . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         1.831
_refine_diff_density_min         -0.695
_refine_diff_density_rms         0.094
_database_code_depnum_ccdc_archive 'CCDC 984156'
#######################################################################
#
#                 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_4ia_35dnsa_21_mecn_40

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H10 I N3 O7'
_chemical_formula_weight         447.14

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'
I I -0.4742 1.8119 '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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.3806(15)
_cell_length_b                   9.3433(18)
_cell_length_c                   11.754(2)
_cell_angle_alpha                80.602(5)
_cell_angle_beta                 71.795(5)
_cell_angle_gamma                79.460(5)
_cell_volume                     752.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.974
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             436
_exptl_absorpt_coefficient_mu    2.173
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.8701
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18894
_diffrn_reflns_av_R_equivalents  0.0327
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.05
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3419
_reflns_number_gt                3209
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2σ(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.

All H-atoms were placed in calculated positions and refined as riding on the 
atoms to which they were bonded with the exception of those involved in hydrogen
bonding. The anilinium group (NH3+) hydrogens H5, H6, H7 and the hydroxyl 
hydrogen H10 were identified using a Fourier difference synthesis and 
their positions and isotropic displacement parameters allowed to freely refine.

;

_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)+(0.0230P)²+0.3034P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3419
_refine_ls_number_parameters     233
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0211
_refine_ls_R_factor_gt           0.0191
_refine_ls_wR_factor_ref         0.0474
_refine_ls_wR_factor_gt          0.0462
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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
H5 H 0.951(3) 0.361(3) 0.154(2) 0.026(6) Uiso 1 1 d . . .
H6 H 0.977(3) 0.449(3) 0.229(2) 0.026(6) Uiso 1 1 d . . .
H7 H 0.856(3) 0.522(3) 0.154(2) 0.029(6) Uiso 1 1 d . . .
H10 H -0.048(4) -0.038(3) 0.878(3) 0.051(8) Uiso 1 1 d . . .
I1 I 0.164023(17) 0.243642(14) 0.610627(11) 0.02488(5) Uani 1 1 d . . .
O1 O -0.08805(18) 0.07068(14) 0.87313(11) 0.0183(3) Uani 1 1 d . . .
O2 O -0.04762(17) -0.19667(13) 0.92650(12) 0.0184(3) Uani 1 1 d . . .
O5 O -0.80750(18) 0.24940(14) 1.29321(12) 0.0211(3) Uani 1 1 d . . .
O3 O -0.23853(19) -0.29969(13) 1.09584(12) 0.0214(3) Uani 1 1 d . . .
O7 O -0.2235(2) 0.35581(15) 0.81981(12) 0.0270(3) Uani 1 1 d . . .
N1 N -0.2730(2) 0.35245(16) 0.92947(14) 0.0182(3) Uani 1 1 d . . .
N3 N 0.8898(2) 0.43444(17) 0.19927(14) 0.0161(3) Uani 1 1 d . . .
N2 N -0.7166(2) 0.12574(17) 1.28099(14) 0.0179(3) Uani 1 1 d . . .
O4 O -0.7621(2) 0.01603(15) 1.34917(13) 0.0276(3) Uani 1 1 d . . .
O6 O -0.2749(2) 0.45631(14) 0.98194(13) 0.0250(3) Uani 1 1 d . . .
C13 C -0.1875(2) -0.19284(19) 1.02458(16) 0.0160(3) Uani 1 1 d . . .
C10 C -0.4494(2) -0.02822(19) 1.15308(16) 0.0148(3) Uani 1 1 d . . .
H10A H -0.4884 -0.1106 1.2049 0.018 Uiso 1 1 calc R . .
C7 C -0.3348(2) 0.21929(18) 1.00336(16) 0.0147(3) Uani 1 1 d . . .
C9 C -0.2945(2) -0.04284(18) 1.05087(16) 0.0141(3) Uani 1 1 d . . .
C1 C 0.4034(3) 0.3062(2) 0.47266(16) 0.0196(4) Uani 1 1 d . . .
C8 C -0.2354(2) 0.08202(19) 0.97157(16) 0.0148(3) Uani 1 1 d . . .
C11 C -0.5461(2) 0.10977(19) 1.17785(16) 0.0150(3) Uani 1 1 d . . .
C4 C 0.7204(2) 0.38903(19) 0.29444(16) 0.0161(3) Uani 1 1 d . . .
C12 C -0.4880(2) 0.23537(18) 1.10582(16) 0.0150(3) Uani 1 1 d . . .
H12 H -0.5502 0.3277 1.1259 0.018 Uiso 1 1 calc R . .
C5 C 0.7362(3) 0.2541(2) 0.36139(18) 0.0225(4) Uani 1 1 d . . .
H5A H 0.8528 0.1920 0.3462 0.027 Uiso 1 1 calc R . .
C3 C 0.5487(3) 0.48277(19) 0.31390(16) 0.0180(4) Uani 1 1 d . . .
H3 H 0.5404 0.5729 0.2673 0.022 Uiso 1 1 calc R . .
C2 C 0.3886(3) 0.4407(2) 0.40383(18) 0.0210(4) Uani 1 1 d . . .
H2 H 0.2718 0.5026 0.4179 0.025 Uiso 1 1 calc R . .
C6 C 0.5760(3) 0.2120(2) 0.45181(18) 0.0235(4) Uani 1 1 d . . .
H6A H 0.5844 0.1215 0.4979 0.028 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 0.02212(7) 0.03347(8) 0.01732(7) -0.00296(5) 0.00100(5) -0.01138(5)
O1 0.0167(6) 0.0170(6) 0.0178(6) -0.0010(5) -0.0013(5) -0.0012(5)
O2 0.0173(6) 0.0158(6) 0.0208(7) -0.0043(5) -0.0045(5) 0.0012(5)
O5 0.0171(6) 0.0233(7) 0.0214(7) -0.0070(5) -0.0051(5) 0.0042(5)
O3 0.0253(7) 0.0126(6) 0.0234(7) -0.0003(5) -0.0058(6) 0.0005(5)
O7 0.0313(8) 0.0223(7) 0.0192(7) 0.0045(5) -0.0009(6) -0.0004(6)
N1 0.0140(7) 0.0145(7) 0.0237(8) 0.0015(6) -0.0043(6) -0.0009(6)
N3 0.0155(7) 0.0136(7) 0.0169(8) -0.0010(6) -0.0024(6) -0.0009(6)
N2 0.0167(7) 0.0218(8) 0.0149(7) -0.0032(6) -0.0046(6) -0.0008(6)
O4 0.0292(7) 0.0246(7) 0.0210(7) 0.0027(6) 0.0025(6) -0.0055(6)
O6 0.0296(7) 0.0135(6) 0.0333(8) -0.0015(6) -0.0109(6) -0.0044(5)
C13 0.0166(8) 0.0148(8) 0.0191(9) -0.0039(7) -0.0089(7) -0.0001(6)
C10 0.0155(8) 0.0144(8) 0.0158(8) 0.0007(6) -0.0073(7) -0.0030(6)
C7 0.0157(8) 0.0124(8) 0.0168(8) 0.0016(6) -0.0072(7) -0.0029(6)
C9 0.0145(8) 0.0123(8) 0.0167(8) -0.0018(6) -0.0069(7) -0.0004(6)
C1 0.0185(8) 0.0269(9) 0.0145(8) -0.0033(7) -0.0025(7) -0.0089(7)
C8 0.0128(8) 0.0173(8) 0.0160(8) -0.0030(7) -0.0060(6) -0.0019(6)
C11 0.0131(8) 0.0182(8) 0.0136(8) -0.0023(7) -0.0041(6) -0.0012(6)
C4 0.0161(8) 0.0170(8) 0.0147(8) -0.0021(7) -0.0029(7) -0.0034(7)
C12 0.0153(8) 0.0126(8) 0.0184(9) -0.0028(6) -0.0076(7) 0.0003(6)
C5 0.0177(9) 0.0203(9) 0.0252(10) 0.0018(7) -0.0036(7) -0.0005(7)
C3 0.0195(9) 0.0155(8) 0.0170(9) -0.0008(7) -0.0037(7) -0.0012(7)
C2 0.0159(8) 0.0224(9) 0.0231(10) -0.0061(7) -0.0032(7) -0.0001(7)
C6 0.0241(9) 0.0218(9) 0.0224(10) 0.0051(8) -0.0068(8) -0.0049(8)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 2.0907(18) . ?
O1 C8 1.321(2) . ?
O2 C13 1.286(2) . ?
O5 N2 1.2314(19) . ?
O3 C13 1.228(2) . ?
O7 N1 1.222(2) . ?
N1 O6 1.228(2) . ?
N1 C7 1.455(2) . ?
N3 C4 1.470(2) . ?
N2 O4 1.223(2) . ?
N2 C11 1.453(2) . ?
C13 C9 1.506(2) . ?
C10 C9 1.381(2) . ?
C10 C11 1.383(2) . ?
C7 C12 1.377(2) . ?
C7 C8 1.401(2) . ?
C9 C8 1.413(2) . ?
C1 C2 1.385(3) . ?
C1 C6 1.386(3) . ?
C11 C12 1.382(2) . ?
C4 C5 1.379(3) . ?
C4 C3 1.380(2) . ?
C5 C6 1.390(3) . ?
C3 C2 1.386(3) . ?

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
O7 N1 O6 123.60(16) . . ?
O7 N1 C7 118.98(15) . . ?
O6 N1 C7 117.41(15) . . ?
O4 N2 O5 124.13(15) . . ?
O4 N2 C11 118.30(14) . . ?
O5 N2 C11 117.57(15) . . ?
O3 C13 O2 125.48(16) . . ?
O3 C13 C9 119.03(16) . . ?
O2 C13 C9 115.50(15) . . ?
C9 C10 C11 119.56(16) . . ?
C12 C7 C8 122.61(16) . . ?
C12 C7 N1 117.26(15) . . ?
C8 C7 N1 120.09(16) . . ?
C10 C9 C8 120.40(15) . . ?
C10 C9 C13 119.62(16) . . ?
C8 C9 C13 119.99(15) . . ?
C2 C1 C6 120.82(17) . . ?
C2 C1 I1 119.98(13) . . ?
C6 C1 I1 119.20(14) . . ?
O1 C8 C7 121.01(16) . . ?
O1 C8 C9 121.47(15) . . ?
C7 C8 C9 117.49(16) . . ?
C12 C11 C10 122.01(16) . . ?
C12 C11 N2 117.98(15) . . ?
C10 C11 N2 120.00(16) . . ?
C5 C4 C3 121.67(16) . . ?
C5 C4 N3 119.47(15) . . ?
C3 C4 N3 118.86(16) . . ?
C7 C12 C11 117.83(15) . . ?
C4 C5 C6 119.29(17) . . ?
C4 C3 C2 119.10(17) . . ?
C1 C2 C3 119.75(17) . . ?
C1 C6 C5 119.37(18) . . ?

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
O1 H10 O2 1.00(3) 1.50(3) 2.4606(18) 159(3) .
N3 H6 O5 0.86(3) 2.41(2) 2.950(2) 121.5(19) 1_754
N3 H6 O7 0.86(3) 2.68(3) 3.352(2) 136(2) 2_666
N3 H7 O3 0.94(3) 1.80(3) 2.724(2) 168(2) 1_664

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.508
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.081
_database_code_depnum_ccdc_archive 'CCDC 984157'
#######################################################################
#
#                 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_4ia_35dnsa_ipa_21_rt

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C32 H26 I3 N7 O14'
_chemical_formula_weight         1113.30

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'
I I -0.4742 1.8119 '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'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   9.0879(11)
_cell_length_b                   9.9637(12)
_cell_length_c                   10.5749(12)
_cell_angle_alpha                94.099(4)
_cell_angle_beta                 103.810(4)
_cell_angle_gamma                92.568(4)
_cell_volume                     925.59(19)
_cell_formula_units_Z            1
_cell_measurement_temperature    100
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.997
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             538
_exptl_absorpt_coefficient_mu    2.611
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.7820
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22287
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0255
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         27.49
_reflns_number_total             4221
_reflns_number_gt                3036
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2σ(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.

One 4-iodoaniline molecule is 50:50 disordered over an inversion centre. 
In order to ensure chemically sensible bond lengths and angles were obtained,
the benzene ring of this disordered molecule was constrained to take a
standard geometry using an AFIX 66 command and the anisotropic displacement
parameters for all carbon atoms in the ring (C70-C75) were constrained to 
take the same value using the EADP command.  Relaxation of this constraint
resulted in unreasonable anisotropic displacement parameters for these atoms.
The two positions for the 4IA molecule are displaced such that the I and N 
positions are very close.  A series of constraints thus had to be applied to 
ensure that the C-C-N70/I2 angles and C-N70/I2 distances took approximately 
standard values. Firstly the EADP command was used to constrain the 
anisotropic displacement parameters of N70 and I2 to be the same; this was 
due to the close proximity of the two positions. SADI constraints were 
applied to ensure the C-C-I/N angles were chemically sensible; the C71-I2 
bond length was constrained to be similar to the ordered C12-I1 bond length; 
the C74-N70 bond length was constrained to be similar to the C9-N4 bond length; 
the C-C-I/N bond angles on either side of the I/N group were constrained to be 
equal i.e. the C70-I2 distance should be the same as the C72-I2 distance and 
the C73-N70 distance should be the same as the C75-N70 distance.  

All H-atoms were placed in calculated positions and refined as riding on the 
atoms to which they were bonded with the exception of those involved in hydrogen
bonding. The anilinium group (NH3+) hydrogens H20, H21, H22 and the hydroxyl 
hydrogen H7 were identified using a Fourier difference synthesis and 
their positions and isotropic displacement parameters allowed to freely refine.

;

_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)+(0.0232P)²+3.1374P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4221
_refine_ls_number_parameters     257
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0657
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.1110
_refine_ls_wR_factor_gt          0.0788
_refine_ls_goodness_of_fit_ref   1.193
_refine_ls_restrained_S_all      1.194
_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
I2 I 0.82654(11) -0.06100(12) 0.58980(13) 0.0639(3) Uani 0.50 1 d PD A 1
N70 N 0.1447(16) 0.0892(16) 0.4017(18) 0.0639(3) Uani 0.50 1 d PD B 1
H70A H 0.1245 0.1723 0.4116 0.077 Uiso 0.50 1 calc PR B 1
H70B H 0.0735 0.0294 0.3645 0.077 Uiso 0.50 1 calc PR B 1
C70 C 0.5609(7) 0.1162(7) 0.5472(8) 0.0571(12) Uani 0.50 1 d PGD C 1
H70 H 0.6362 0.1824 0.5871 0.068 Uiso 0.50 1 calc PR C 1
C71 C 0.5983(6) -0.0161(8) 0.5272(9) 0.0571(12) Uani 0.50 1 d PGD . 1
C72 C 0.4857(7) -0.1152(6) 0.4674(8) 0.0571(12) Uani 0.50 1 d PGD . 1
H72 H 0.5108 -0.2037 0.4541 0.068 Uiso 0.50 1 calc PR C 1
C73 C 0.3357(6) -0.0820(7) 0.4276(7) 0.0571(12) Uani 0.50 1 d PGD C 1
H73 H 0.2604 -0.1482 0.3876 0.068 Uiso 0.50 1 calc PR C 1
C74 C 0.2983(6) 0.0503(7) 0.4476(7) 0.0571(12) Uani 0.50 1 d PGD . 1
C75 C 0.4108(8) 0.1494(6) 0.5073(7) 0.0571(12) Uani 0.50 1 d PGD C 1
H75 H 0.3858 0.2379 0.5207 0.068 Uiso 0.50 1 calc PR C 1
N4 N -0.1016(5) 0.6238(4) 0.1311(4) 0.0363(9) Uani 1 1 d D . .
H7 H 0.476(9) -0.389(7) 0.062(7) 0.09(2) Uiso 1 1 d . . .
H21 H -0.051(7) 0.672(6) 0.079(6) 0.057(17) Uiso 1 1 d . . .
H20 H -0.130(5) 0.550(5) 0.096(5) 0.028(13) Uiso 1 1 d . . .
H22 H -0.186(7) 0.670(6) 0.137(5) 0.052(16) Uiso 1 1 d . . .
I1 I 0.36613(4) 0.54214(4) 0.66137(4) 0.05879(15) Uani 1 1 d D . .
O3 O 0.1526(4) -0.3553(3) 0.0040(3) 0.0435(8) Uani 1 1 d . . .
O1 O 0.6072(4) -0.2747(3) 0.1240(4) 0.0447(8) Uani 1 1 d . . .
O2 O 0.3825(4) -0.4263(4) 0.0321(4) 0.0524(10) Uani 1 1 d . . .
N1 N 0.7445(4) -0.0057(4) 0.2184(4) 0.0416(9) Uani 1 1 d . . .
C6 C 0.5242(5) -0.1735(4) 0.1286(4) 0.0329(9) Uani 1 1 d . . .
O7 O 0.8331(4) -0.0902(4) 0.2064(6) 0.0795(15) Uani 1 1 d . . .
O4 O 0.1047(4) 0.1373(4) 0.0629(6) 0.0797(15) Uani 1 1 d . . .
C2 C 0.2695(5) -0.0859(5) 0.0816(4) 0.0345(9) Uani 1 1 d . . .
H2 H 0.1647 -0.1002 0.0517 0.041 Uiso 1 1 calc R . .
O5 O 0.2987(4) 0.2704(4) 0.1492(5) 0.0616(11) Uani 1 1 d . . .
C9 C 0.0020(5) 0.6011(4) 0.2565(4) 0.0353(10) Uani 1 1 d D . .
C4 C 0.4894(5) 0.0673(5) 0.1713(4) 0.0344(9) Uani 1 1 d . . .
H4 H 0.5304 0.1540 0.2020 0.041 Uiso 1 1 calc R . .
C20 C 0.2900(5) -0.3301(5) 0.0377(5) 0.0359(10) Uani 1 1 d . . .
N2 N 0.2401(5) 0.1580(4) 0.1127(4) 0.0468(10) Uani 1 1 d . . .
C1 C 0.3618(5) -0.1929(4) 0.0848(4) 0.0315(9) Uani 1 1 d . . .
O6 O 0.7879(4) 0.1089(4) 0.2619(5) 0.0738(14) Uani 1 1 d . . .
C3 C 0.3350(5) 0.0426(4) 0.1234(5) 0.0344(9) Uani 1 1 d . . .
C12 C 0.2055(5) 0.5654(5) 0.4868(5) 0.0409(11) Uani 1 1 d D . .
C8 C 0.1044(6) 0.5024(5) 0.2593(5) 0.0463(12) Uani 1 1 d . . .
H8 H 0.1039 0.4481 0.1839 0.056 Uiso 1 1 calc R . .
C5 C 0.5821(5) -0.0390(4) 0.1729(4) 0.0331(9) Uani 1 1 d . . .
C10 C -0.0021(6) 0.6785(5) 0.3678(5) 0.0456(12) Uani 1 1 d . . .
H10 H -0.0735 0.7429 0.3650 0.055 Uiso 1 1 calc R . .
C13 C 0.2075(6) 0.4852(6) 0.3752(5) 0.0495(13) Uani 1 1 d . . .
H13 H 0.2780 0.4199 0.3781 0.059 Uiso 1 1 calc R . .
C11 C 0.1003(6) 0.6606(5) 0.4845(5) 0.0484(12) Uani 1 1 d . . .
H11 H 0.0979 0.7125 0.5606 0.058 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
I2 0.0503(5) 0.0766(7) 0.0717(5) 0.0157(5) 0.0225(4) 0.0213(4)
N70 0.0503(5) 0.0766(7) 0.0717(5) 0.0157(5) 0.0225(4) 0.0213(4)
C70 0.053(3) 0.063(3) 0.052(3) 0.007(2) 0.008(3) -0.013(3)
C71 0.053(3) 0.063(3) 0.052(3) 0.007(2) 0.008(3) -0.013(3)
C72 0.053(3) 0.063(3) 0.052(3) 0.007(2) 0.008(3) -0.013(3)
C73 0.053(3) 0.063(3) 0.052(3) 0.007(2) 0.008(3) -0.013(3)
C74 0.053(3) 0.063(3) 0.052(3) 0.007(2) 0.008(3) -0.013(3)
C75 0.053(3) 0.063(3) 0.052(3) 0.007(2) 0.008(3) -0.013(3)
N4 0.029(2) 0.031(2) 0.044(2) -0.0013(18) 0.0003(17) 0.0030(17)
I1 0.0494(2) 0.0667(3) 0.0505(2) 0.00808(17) -0.00777(16) 0.00306(17)
O3 0.0362(18) 0.0341(17) 0.056(2) -0.0030(15) 0.0055(15) 0.0000(14)
O1 0.0315(16) 0.0338(17) 0.065(2) -0.0036(15) 0.0044(15) 0.0092(13)
O2 0.0329(18) 0.0341(18) 0.083(3) -0.0109(18) 0.0050(18) 0.0039(15)
N1 0.033(2) 0.042(2) 0.044(2) -0.0030(18) -0.0007(17) 0.0053(17)
C6 0.032(2) 0.031(2) 0.033(2) 0.0007(17) 0.0025(17) 0.0075(17)
O7 0.0321(19) 0.049(2) 0.143(4) -0.013(3) -0.004(2) 0.0109(17)
O4 0.033(2) 0.052(2) 0.138(4) -0.007(3) -0.007(2) 0.0155(18)
C2 0.0230(19) 0.038(2) 0.040(2) 0.0019(19) 0.0029(17) 0.0049(17)
O5 0.050(2) 0.0320(19) 0.094(3) -0.0108(19) 0.006(2) 0.0064(16)
C9 0.025(2) 0.034(2) 0.043(2) -0.0019(19) 0.0022(18) 0.0029(17)
C4 0.034(2) 0.035(2) 0.031(2) 0.0009(17) 0.0022(17) 0.0034(18)
C20 0.029(2) 0.035(2) 0.041(2) 0.0016(19) 0.0033(18) 0.0017(18)
N2 0.038(2) 0.036(2) 0.062(3) -0.0023(19) 0.005(2) 0.0101(18)
C1 0.028(2) 0.030(2) 0.034(2) 0.0025(17) 0.0037(17) 0.0022(16)
O6 0.038(2) 0.050(2) 0.115(4) -0.034(2) -0.004(2) -0.0032(17)
C3 0.033(2) 0.024(2) 0.045(2) -0.0013(18) 0.0057(18) 0.0086(17)
C12 0.033(2) 0.039(3) 0.044(3) 0.005(2) -0.0031(19) -0.0001(19)
C8 0.044(3) 0.048(3) 0.044(3) -0.006(2) 0.005(2) 0.015(2)
C5 0.028(2) 0.036(2) 0.032(2) 0.0030(17) 0.0003(17) 0.0043(17)
C10 0.041(3) 0.037(3) 0.053(3) -0.007(2) 0.003(2) 0.013(2)
C13 0.043(3) 0.054(3) 0.051(3) 0.002(2) 0.006(2) 0.019(2)
C11 0.049(3) 0.045(3) 0.043(3) -0.012(2) 0.000(2) 0.006(2)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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
I2 C71 2.100(5) . ?
N70 C74 1.444(13) . ?
C70 C71 1.3900 . ?
C70 C75 1.3900 . ?
C71 C72 1.3900 . ?
C71 C72 1.548(14) 2_656 ?
C71 C70 1.709(10) 2_656 ?
C72 C73 1.3900 . ?
C72 C74 2.010(13) 2_656 ?
C73 C74 1.3900 . ?
C74 C75 1.3900 . ?
C74 C72 2.010(10) 2_656 ?
N4 C9 1.471(6) . ?
I1 C12 2.097(4) . ?
O3 C20 1.223(5) . ?
O1 C6 1.292(5) . ?
O2 C20 1.311(6) . ?
N1 O7 1.211(5) . ?
N1 O6 1.212(5) . ?
N1 C5 1.454(6) . ?
C6 C5 1.421(6) . ?
C6 C1 1.437(6) . ?
O4 N2 1.219(5) . ?
C2 C1 1.383(6) . ?
C2 C3 1.384(6) . ?
O5 N2 1.214(5) . ?
C9 C10 1.369(7) . ?
C9 C8 1.381(6) . ?
C4 C3 1.377(6) . ?
C4 C5 1.381(6) . ?
C20 C1 1.486(6) . ?
N2 C3 1.463(5) . ?
C12 C11 1.374(7) . ?
C12 C13 1.382(7) . ?
C8 C13 1.380(7) . ?
C10 C11 1.386(7) . ?

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
C71 C70 C75 120.0 . . ?
C70 C71 C72 120.0 . . ?
C70 C71 C72 15.0(4) . 2_656 ?
C72 C71 C72 105.0(4) . 2_656 ?
C70 C71 C70 110.2(4) . 2_656 ?
C72 C71 C70 9.8(4) . 2_656 ?
C72 C71 C70 95.2(6) 2_656 2_656 ?
C70 C71 I2 118.5(4) . . ?
C72 C71 I2 121.5(4) . . ?
C72 C71 I2 133.5(5) 2_656 . ?
C70 C71 I2 131.4(7) 2_656 . ?
C73 C72 C71 120.0 . . ?
C73 C72 C74 147.0(5) . 2_656 ?
C71 C72 C74 27.0(5) . 2_656 ?
C72 C73 C74 120.0 . . ?
C75 C74 C73 120.0 . . ?
C75 C74 N70 118.6(7) . . ?
C73 C74 N70 121.3(7) . . ?
C75 C74 C72 27.0(4) . 2_656 ?
C73 C74 C72 93.0(4) . 2_656 ?
N70 C74 C72 145.6(8) . 2_656 ?
C74 C75 C70 120.0 . . ?
O7 N1 O6 121.5(4) . . ?
O7 N1 C5 119.8(4) . . ?
O6 N1 C5 118.6(4) . . ?
O1 C6 C5 124.5(4) . . ?
O1 C6 C1 119.8(4) . . ?
C5 C6 C1 115.7(4) . . ?
C1 C2 C3 119.2(4) . . ?
C10 C9 C8 121.0(4) . . ?
C10 C9 N4 120.1(4) . . ?
C8 C9 N4 118.9(4) . . ?
C3 C4 C5 118.8(4) . . ?
O3 C20 O2 120.1(4) . . ?
O3 C20 C1 123.6(4) . . ?
O2 C20 C1 116.4(4) . . ?
O5 N2 O4 122.5(4) . . ?
O5 N2 C3 119.4(4) . . ?
O4 N2 C3 118.1(4) . . ?
C2 C1 C6 121.6(4) . . ?
C2 C1 C20 118.6(4) . . ?
C6 C1 C20 119.8(4) . . ?
C4 C3 C2 122.1(4) . . ?
C4 C3 N2 118.0(4) . . ?
C2 C3 N2 119.9(4) . . ?
C11 C12 C13 120.8(4) . . ?
C11 C12 I1 119.7(4) . . ?
C13 C12 I1 119.5(4) . . ?
C13 C8 C9 119.3(5) . . ?
C4 C5 C6 122.5(4) . . ?
C4 C5 N1 116.3(4) . . ?
C6 C5 N1 121.1(4) . . ?
C9 C10 C11 119.8(4) . . ?
C8 C13 C12 119.7(5) . . ?
C12 C11 C10 119.3(5) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         1.209
_refine_diff_density_min         -1.434
_refine_diff_density_rms         0.144
_database_code_depnum_ccdc_archive 'CCDC 984158'
#######################################################################
#
#                 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_4i2ma_35dnba_etoac_11_4deg

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 I N3 O6'
_chemical_formula_weight         445.17

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           ?
_symmetry_space_group_name_H-M   P_1_21_1

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

_cell_length_a                   10.756(9)
_cell_length_b                   5.790(4)
_cell_length_c                   13.363(9)
_cell_angle_alpha                90.000
_cell_angle_beta                 107.859(8)
_cell_angle_gamma                90.000
_cell_volume                     792.1(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.866
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             436
_exptl_absorpt_coefficient_mu    2.058
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 2010)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18081
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0177
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.20
_diffrn_reflns_theta_max         27.47
_reflns_number_total             3620
_reflns_number_gt                3583
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2σ(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.

All H-atoms were placed in calculated positions and refined as riding on the 
atoms to which they were bonded with the exception of those involved in hydrogen
bonding. The anilinium NH3+ group hydrogens H1A, H1B and H1C were identified 
using a Fourier difference synthesis and their positions and isotropic 
displacement parameters allowed to freely refine.

;

_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)+(0.0195P)²+0.0696P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_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   -0.010(9)
_refine_ls_number_reflns         3620
_refine_ls_number_parameters     230
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0133
_refine_ls_R_factor_gt           0.0131
_refine_ls_wR_factor_ref         0.0332
_refine_ls_wR_factor_gt          0.0332
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.087
_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 0.210429(7) 0.72676(3) 0.204228(6) 0.02089(3) Uani 1 1 d . . .
C5 C -0.12190(16) 0.2760(3) 0.16760(13) 0.0194(4) Uani 1 1 d . . .
H5 H -0.1386 0.1409 0.1988 0.023 Uiso 1 1 calc R . .
C2 C -0.07391(15) 0.6797(2) 0.07253(12) 0.0179(4) Uani 1 1 d . . .
H2 H -0.0565 0.8139 0.0410 0.022 Uiso 1 1 calc R . .
C7 C -0.30910(15) 0.7066(4) -0.04095(12) 0.0223(3) Uani 1 1 d . . .
H7A H -0.3600 0.5938 -0.0889 0.033 Uiso 1 1 calc R . .
H7B H -0.2729 0.8150 -0.0788 0.033 Uiso 1 1 calc R . .
H7C H -0.3639 0.7868 -0.0077 0.033 Uiso 1 1 calc R . .
C3 C -0.19999(15) 0.5875(3) 0.04150(12) 0.0164(3) Uani 1 1 d . . .
C4 C -0.22201(15) 0.3873(3) 0.09212(12) 0.0157(3) Uani 1 1 d . . .
C1 C 0.02550(15) 0.5721(3) 0.15012(12) 0.0178(3) Uani 1 1 d . . .
C6 C 0.00348(16) 0.3679(3) 0.19622(13) 0.0202(3) Uani 1 1 d . . .
H6 H 0.0718 0.2933 0.2457 0.024 Uiso 1 1 calc R . .
N1 N -0.35523(14) 0.2994(3) 0.06871(12) 0.0159(3) Uani 1 1 d . . .
N4 N 0.08454(15) 0.1017(3) 0.44327(13) 0.0227(4) Uani 1 1 d . . .
O4 O 0.48560(11) 0.16417(18) 0.87390(9) 0.0182(2) Uani 1 1 d . . .
C15 C 0.40322(14) 0.2590(3) 0.79540(12) 0.0159(4) Uani 1 1 d . . .
O2 O 0.04091(16) 0.2960(3) 0.44609(12) 0.0356(4) Uani 1 1 d . . .
O1 O 0.03788(12) -0.0409(2) 0.37400(10) 0.0263(3) Uani 1 1 d . . .
O3 O 0.35735(12) 0.4574(2) 0.79231(10) 0.0218(2) Uani 1 1 d . . .
C9 C 0.38223(16) -0.2131(2) 0.59501(12) 0.0154(3) Uani 1 1 d . . .
C8 C 0.26923(16) -0.1597(3) 0.51463(13) 0.0173(3) Uani 1 1 d . . .
H8 H 0.2396 -0.2509 0.4547 0.021 Uiso 1 1 calc R . .
C11 C 0.35624(15) 0.1130(3) 0.69649(12) 0.0149(3) Uani 1 1 d . . .
C12 C 0.24404(15) 0.1754(2) 0.61680(12) 0.0164(3) Uani 1 1 d . . .
H12 H 0.1976 0.3075 0.6228 0.020 Uiso 1 1 calc R . .
C10 C 0.42699(15) -0.0820(3) 0.68579(12) 0.0153(3) Uani 1 1 d . . .
H10 H 0.5027 -0.1234 0.7385 0.018 Uiso 1 1 calc R . .
C13 C 0.20303(15) 0.0370(3) 0.52851(12) 0.0169(3) Uani 1 1 d . . .
O6 O 0.41146(13) -0.5384(2) 0.50480(10) 0.0241(3) Uani 1 1 d . . .
O5 O 0.55917(13) -0.4576(2) 0.65162(10) 0.0278(3) Uani 1 1 d . . .
N3 N 0.45662(14) -0.4180(2) 0.58259(11) 0.0191(3) Uani 1 1 d . . .
H1A H -0.398(2) 0.270(4) -0.0009(17) 0.027(6) Uiso 1 1 d . . .
H1B H -0.356(2) 0.184(5) 0.1007(17) 0.021(6) Uiso 1 1 d . . .
H1C H -0.403(2) 0.406(5) 0.093(2) 0.035(6) Uiso 1 1 d . . .

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 0.01591(5) 0.02508(5) 0.02178(5) -0.00388(6) 0.00595(3) -0.00467(5)
C5 0.0189(7) 0.0183(10) 0.0193(7) 0.0037(6) 0.0031(6) -0.0012(5)
C2 0.0201(7) 0.0166(10) 0.0180(7) 0.0003(6) 0.0072(6) 0.0000(5)
C7 0.0193(6) 0.0226(9) 0.0233(7) 0.0092(9) 0.0041(5) 0.0015(8)
C3 0.0182(7) 0.0161(7) 0.0153(7) 0.0018(6) 0.0058(6) 0.0021(6)
C4 0.0160(7) 0.0150(7) 0.0145(7) -0.0023(6) 0.0023(6) -0.0013(6)
C1 0.0167(7) 0.0201(7) 0.0169(7) -0.0044(6) 0.0057(6) -0.0022(6)
C6 0.0183(8) 0.0223(8) 0.0170(8) 0.0015(7) 0.0011(6) 0.0009(6)
N1 0.0160(6) 0.0146(6) 0.0149(7) 0.0015(6) 0.0014(6) -0.0010(5)
N4 0.0191(8) 0.0347(9) 0.0143(7) 0.0014(6) 0.0050(6) 0.0065(6)
O4 0.0170(5) 0.0203(6) 0.0147(5) -0.0017(4) 0.0011(4) -0.0010(4)
C15 0.0155(6) 0.0154(10) 0.0179(6) 0.0001(7) 0.0068(5) -0.0023(6)
O2 0.0386(8) 0.0444(10) 0.0188(6) 0.0001(6) 0.0015(6) 0.0272(7)
O1 0.0211(6) 0.0371(7) 0.0169(6) -0.0010(6) 0.0004(5) -0.0013(5)
O3 0.0266(6) 0.0168(6) 0.0207(6) -0.0037(5) 0.0051(5) 0.0030(5)
C9 0.0185(7) 0.0130(8) 0.0159(7) 0.0013(5) 0.0073(6) 0.0019(5)
C8 0.0179(7) 0.0191(8) 0.0151(7) -0.0006(6) 0.0055(6) -0.0020(6)
C11 0.0166(7) 0.0144(7) 0.0142(7) 0.0010(6) 0.0054(6) -0.0004(6)
C12 0.0159(6) 0.0172(10) 0.0169(6) 0.0014(5) 0.0062(5) 0.0023(5)
C10 0.0145(7) 0.0167(7) 0.0140(7) 0.0032(6) 0.0034(6) 0.0005(6)
C13 0.0141(7) 0.0224(8) 0.0139(7) 0.0028(6) 0.0038(6) 0.0015(6)
O6 0.0300(6) 0.0201(6) 0.0240(6) -0.0054(5) 0.0108(5) -0.0002(5)
O5 0.0254(6) 0.0284(7) 0.0270(6) 0.0009(5) 0.0040(5) 0.0123(5)
N3 0.0226(7) 0.0161(6) 0.0209(7) 0.0012(5) 0.0103(6) 0.0027(5)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 2.0973(18) . ?
C5 C4 1.388(2) . ?
C5 C6 1.390(2) . ?
C2 C1 1.388(2) . ?
C2 C3 1.397(2) . ?
C7 C3 1.508(2) . ?
C3 C4 1.398(2) . ?
C4 N1 1.461(2) . ?
C1 C6 1.387(3) . ?
N4 O2 1.224(2) . ?
N4 O1 1.227(2) . ?
N4 C13 1.474(2) . ?
O4 C15 1.272(2) . ?
C15 O3 1.246(2) . ?
C15 C11 1.519(2) . ?
C9 C10 1.386(2) . ?
C9 C8 1.388(2) . ?
C9 N3 1.469(2) . ?
C8 C13 1.385(2) . ?
C11 C12 1.390(2) . ?
C11 C10 1.393(2) . ?
C12 C13 1.382(2) . ?
O6 N3 1.222(2) . ?
O5 N3 1.2232(19) . ?

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
C4 C5 C6 119.58(15) . . ?
C1 C2 C3 120.38(14) . . ?
C2 C3 C4 117.79(14) . . ?
C2 C3 C7 120.62(15) . . ?
C4 C3 C7 121.55(15) . . ?
C5 C4 C3 121.84(15) . . ?
C5 C4 N1 119.03(15) . . ?
C3 C4 N1 119.05(14) . . ?
C6 C1 C2 121.13(15) . . ?
C6 C1 I1 118.94(12) . . ?
C2 C1 I1 119.87(12) . . ?
C1 C6 C5 119.17(15) . . ?
O2 N4 O1 124.74(18) . . ?
O2 N4 C13 117.31(18) . . ?
O1 N4 C13 117.94(16) . . ?
O3 C15 O4 126.46(15) . . ?
O3 C15 C11 117.50(14) . . ?
O4 C15 C11 116.03(15) . . ?
C10 C9 C8 122.82(14) . . ?
C10 C9 N3 119.09(14) . . ?
C8 C9 N3 118.09(14) . . ?
C13 C8 C9 116.35(15) . . ?
C12 C11 C10 120.35(14) . . ?
C12 C11 C15 120.04(14) . . ?
C10 C11 C15 119.60(14) . . ?
C13 C12 C11 118.56(14) . . ?
C9 C10 C11 118.65(15) . . ?
C12 C13 C8 123.25(15) . . ?
C12 C13 N4 119.11(15) . . ?
C8 C13 N4 117.63(15) . . ?
O6 N3 O5 124.47(15) . . ?
O6 N3 C9 117.96(14) . . ?
O5 N3 C9 117.57(14) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.47
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.412
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.055
_database_code_depnum_ccdc_archive 'CCDC 984159'
#######################################################################
#
#                 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_4i2ma_35dnba_mecn_11_rt

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H12 I N3 O6'
_chemical_formula_weight         445.17

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           ?
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.534(2)
_cell_length_b                   8.769(2)
_cell_length_c                   11.882(8)
_cell_angle_alpha                111.035(8)
_cell_angle_beta                 101.327(7)
_cell_angle_gamma                95.273(7)
_cell_volume                     800.9(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.846
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             436
_exptl_absorpt_coefficient_mu    2.036
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.778
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 2010)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18691
_diffrn_reflns_av_R_equivalents  0.0189
_diffrn_reflns_av_sigmaI/netI    0.0126
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.21
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3661
_reflns_number_gt                3500
_reflns_threshold_expression     >2σ(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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 > 2σ(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.

All H-atoms were placed in calculated positions and refined as riding on the 
atoms to which they were bonded with the exception of the hydroxyl hydrogen 
H4 which was identified using a Fourier difference synthesis and the 
positions and isotropic displacement parameters allowed to freely refine.

;

_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)+(0.0253P)²+0.3051P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3661
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0190
_refine_ls_R_factor_gt           0.0180
_refine_ls_wR_factor_ref         0.0475
_refine_ls_wR_factor_gt          0.0471
_refine_ls_goodness_of_fit_ref   1.132
_refine_ls_restrained_S_all      1.132
_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
I1 I 0.692919(12) 0.461055(13) 0.791198(11) 0.03079(5) Uani 1 1 d . . .
O1 O -0.06899(14) -0.37434(13) 0.63058(10) 0.0227(2) Uani 1 1 d . . .
H4 H -0.0708 -0.4703 0.5845 0.034 Uiso 1 1 calc R . .
O2 O 0.07724(13) -0.31383(13) 0.50858(10) 0.0213(2) Uani 1 1 d . . .
O6 O -0.17346(14) 0.05193(15) 0.97671(10) 0.0248(2) Uani 1 1 d . . .
O5 O -0.08146(15) 0.31236(15) 1.02507(11) 0.0279(3) Uani 1 1 d . . .
O3 O 0.25677(14) 0.27652(16) 0.60074(11) 0.0262(2) Uani 1 1 d . . .
O4 O 0.23442(18) 0.46395(15) 0.77245(14) 0.0400(3) Uani 1 1 d . . .
N2 N -0.10005(15) 0.16488(16) 0.95851(11) 0.0196(2) Uani 1 1 d . . .
N3 N 0.34840(16) -0.19892(17) 0.79619(12) 0.0220(3) Uani 1 1 d . . .
H3A H 0.2999 -0.1947 0.8539 0.026 Uiso 1 1 calc R . .
H3B H 0.3450 -0.2927 0.7374 0.026 Uiso 1 1 calc R . .
C6 C 0.11962(17) 0.19286(18) 0.72455(14) 0.0179(3) Uani 1 1 d . . .
C12 C 0.50538(18) -0.06007(19) 0.70032(14) 0.0201(3) Uani 1 1 d . . .
C11 C 0.43174(17) -0.05516(18) 0.79779(14) 0.0183(3) Uani 1 1 d . . .
N1 N 0.21043(16) 0.32046(16) 0.69726(13) 0.0223(3) Uani 1 1 d . . .
C3 C -0.04619(17) -0.04853(18) 0.77650(13) 0.0179(3) Uani 1 1 d . . .
H3 H -0.1033 -0.1289 0.7945 0.021 Uiso 1 1 calc R . .
C14 C 0.5041(2) -0.2246(2) 0.59809(15) 0.0259(3) Uani 1 1 d . . .
H14A H 0.5541 -0.2055 0.5376 0.039 Uiso 1 1 calc R . .
H14B H 0.3940 -0.2810 0.5587 0.039 Uiso 1 1 calc R . .
H14C H 0.5632 -0.2917 0.6331 0.039 Uiso 1 1 calc R . .
C7 C 0.10738(17) 0.02729(18) 0.64831(13) 0.0176(3) Uani 1 1 d . . .
H7 H 0.1541 -0.0020 0.5808 0.021 Uiso 1 1 calc R . .
C10 C 0.43754(18) 0.09793(19) 0.89344(14) 0.0195(3) Uani 1 1 d . . .
H10 H 0.3909 0.1008 0.9585 0.023 Uiso 1 1 calc R . .
C9 C 0.51159(18) 0.24513(19) 0.89283(14) 0.0219(3) Uani 1 1 d . . .
H9 H 0.5149 0.3459 0.9569 0.026 Uiso 1 1 calc R . .
C2 C 0.02342(17) -0.09364(18) 0.67543(13) 0.0175(3) Uani 1 1 d . . .
C4 C -0.02876(17) 0.11860(18) 0.84998(13) 0.0173(3) Uani 1 1 d . . .
C8 C 0.58063(18) 0.2403(2) 0.79565(15) 0.0226(3) Uani 1 1 d . . .
C5 C 0.05405(17) 0.24361(18) 0.82752(13) 0.0181(3) Uani 1 1 d . . .
H5 H 0.0652 0.3550 0.8783 0.022 Uiso 1 1 calc R . .
C13 C 0.57839(18) 0.0887(2) 0.70042(14) 0.0216(3) Uani 1 1 d . . .
H13 H 0.6263 0.0872 0.6363 0.026 Uiso 1 1 calc R . .
C1 C 0.01323(17) -0.27263(18) 0.59666(14) 0.0189(3) Uani 1 1 d . . .

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 0.02754(7) 0.02630(7) 0.04119(8) 0.02124(5) 0.00232(5) -0.00324(4)
O1 0.0286(6) 0.0142(5) 0.0242(5) 0.0045(4) 0.0109(4) 0.0013(4)
O2 0.0233(5) 0.0181(5) 0.0202(5) 0.0035(4) 0.0079(4) 0.0040(4)
O6 0.0259(6) 0.0285(6) 0.0254(6) 0.0133(5) 0.0125(4) 0.0057(4)
O5 0.0310(6) 0.0239(6) 0.0221(5) -0.0006(5) 0.0105(5) 0.0028(5)
O3 0.0245(6) 0.0335(6) 0.0280(6) 0.0175(5) 0.0115(5) 0.0056(5)
O4 0.0530(8) 0.0163(6) 0.0567(9) 0.0107(6) 0.0343(7) 0.0049(5)
N2 0.0181(6) 0.0223(6) 0.0174(6) 0.0060(5) 0.0053(5) 0.0043(5)
N3 0.0267(6) 0.0181(6) 0.0226(6) 0.0080(5) 0.0096(5) 0.0021(5)
C6 0.0169(6) 0.0179(7) 0.0206(7) 0.0089(6) 0.0053(5) 0.0039(5)
C12 0.0176(7) 0.0230(7) 0.0205(7) 0.0093(6) 0.0038(5) 0.0050(5)
C11 0.0163(6) 0.0191(7) 0.0201(7) 0.0091(6) 0.0025(5) 0.0035(5)
N1 0.0210(6) 0.0211(6) 0.0305(7) 0.0139(5) 0.0105(5) 0.0066(5)
C3 0.0176(6) 0.0175(7) 0.0184(7) 0.0073(5) 0.0039(5) 0.0020(5)
C14 0.0270(8) 0.0260(8) 0.0238(7) 0.0064(6) 0.0101(6) 0.0049(6)
C7 0.0171(6) 0.0202(7) 0.0166(6) 0.0076(5) 0.0050(5) 0.0051(5)
C10 0.0193(7) 0.0213(7) 0.0193(7) 0.0091(6) 0.0052(5) 0.0036(5)
C9 0.0221(7) 0.0178(7) 0.0234(7) 0.0072(6) 0.0022(6) 0.0031(5)
C2 0.0172(6) 0.0161(7) 0.0173(6) 0.0048(5) 0.0027(5) 0.0033(5)
C4 0.0171(6) 0.0198(7) 0.0149(6) 0.0059(5) 0.0047(5) 0.0046(5)
C8 0.0191(7) 0.0219(7) 0.0291(8) 0.0156(6) 0.0020(6) -0.0001(5)
C5 0.0172(6) 0.0157(6) 0.0196(7) 0.0049(5) 0.0037(5) 0.0036(5)
C13 0.0182(7) 0.0283(8) 0.0224(7) 0.0143(6) 0.0054(6) 0.0036(6)
C1 0.0171(6) 0.0185(7) 0.0190(7) 0.0058(6) 0.0026(5) 0.0029(5)

_geom_special_details            
;
 All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell s.u.'s are taken
 into account individually in the estimation of s.u.'s in distances, angles
 and torsion angles; correlations between s.u.'s in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell s.u.'s is used for estimating s.u.'s 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 C8 2.1024(18) . ?
O1 C1 1.3055(19) . ?
O2 C1 1.2302(19) . ?
O6 N2 1.2300(18) . ?
O5 N2 1.2255(18) . ?
O3 N1 1.2284(18) . ?
O4 N1 1.2235(19) . ?
N2 C4 1.4751(19) . ?
N3 C11 1.381(2) . ?
C6 C7 1.389(2) . ?
C6 C5 1.390(2) . ?
C6 N1 1.469(2) . ?
C12 C13 1.393(2) . ?
C12 C11 1.412(2) . ?
C12 C14 1.513(2) . ?
C11 C10 1.402(2) . ?
C3 C4 1.387(2) . ?
C3 C2 1.391(2) . ?
C7 C2 1.392(2) . ?
C10 C9 1.387(2) . ?
C9 C8 1.385(2) . ?
C2 C1 1.495(2) . ?
C4 C5 1.383(2) . ?
C8 C13 1.398(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
O5 N2 O6 124.28(13) . . ?
O5 N2 C4 118.23(12) . . ?
O6 N2 C4 117.49(12) . . ?
C7 C6 C5 123.24(14) . . ?
C7 C6 N1 118.43(13) . . ?
C5 C6 N1 118.30(13) . . ?
C13 C12 C11 118.73(14) . . ?
C13 C12 C14 121.10(14) . . ?
C11 C12 C14 120.17(14) . . ?
N3 C11 C10 120.17(14) . . ?
N3 C11 C12 120.32(14) . . ?
C10 C11 C12 119.45(14) . . ?
O4 N1 O3 124.38(14) . . ?
O4 N1 C6 117.54(13) . . ?
O3 N1 C6 118.08(13) . . ?
C4 C3 C2 118.69(13) . . ?
C6 C7 C2 118.37(13) . . ?
C9 C10 C11 121.21(14) . . ?
C8 C9 C10 119.21(14) . . ?
C3 C2 C7 120.39(14) . . ?
C3 C2 C1 120.49(13) . . ?
C7 C2 C1 119.10(13) . . ?
C5 C4 C3 123.26(13) . . ?
C5 C4 N2 118.50(13) . . ?
C3 C4 N2 118.24(13) . . ?
C9 C8 C13 120.45(14) . . ?
C9 C8 I1 120.26(12) . . ?
C13 C8 I1 119.28(12) . . ?
C4 C5 C6 116.05(13) . . ?
C12 C13 C8 120.91(14) . . ?
O2 C1 O1 125.45(14) . . ?
O2 C1 C2 120.97(14) . . ?
O1 C1 C2 113.57(13) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.516
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.069
_database_code_depnum_ccdc_archive 'CCDC 984160'
