Supplementary Material (ESI) for Organic & Biomolecular Chemistry
  This journal is (c) The Royal Society of Chemistry 2006

data_global
_journal_name_full               Org.Biomol.Chem.

_journal_coden_Cambridge         0177

_publ_contact_author_name        'J. Clayden'
_publ_contact_author_address     
;
School of Chemistry
University of Manchester
Oxford Road
MANCHESTER
M13 9PL
UNITED KINGDOM
;

_publ_contact_author_email       J.P.CLAYDEN@MAN.AC.UK

_publ_section_title              
;
Conformational communication between the Ar-CO and
Ar-N axes in 2,2'-disubstituted benzanilides and their derivatives
;

_publ_section_exptl_refinement   
;
The structure was solved by direct methods.
The non-hydrogen atoms were refined anisotropically,
except where the ADP becomes NPD or unrealistic.
H atoms were included in calculated positions,
except where they were largely indeterminate.
;

# Insert blank lines between references

_publ_section_references         
;
#
# Put all your general crystallographic references here
# Delete as required from the document CIF
#

Sheldrick, G.M. (1993) SHELXL93. Program for crystal structure
refinement. University of Gottingen, Germany.

Sheldrick, G.M. (1997) SHELXL97. Program for crystal structure
refinement. University of Gottingen, Germany.

Sheldrick, G.M. (1985). SHELXS86. In Crystallographic Computing 3,
edited by G. M. Sheldrick, C. Kruger & R. Goddard, pp. 175-189.
Oxford University Press.

Sheldrick, G.M. (1997) SHELXS97. Program for Crystal Structure solution.
University of Gottingen, Germany.

Wilson, A.J.C. (1992) Ed. International Tables for Crystallography,
Volume C, Kluwer Academic Publishers, Dordrecht, The Netherlands.
;
_publ_section_figure_captions    
;
Figure 1. View of (I) (50% probability displacement ellipsoids)
;
_publ_section_acknowledgements   
;
?
;
_publ_section_table_legends      
;
Table 1. Fractional atomic coordinates and equivalent
isotropic displacement parameters (\%A^2^)

Table 2. Selected geometric parameters (\%A ,\% )
;
loop_
_publ_author_name
'J. Clayden'
'Madeleine Helliwell'
'Lluis Vallverdu'
#------------------ SECTION 2. COMPOUND(S) DETAILS ------------------------

data_s2040ma
_database_code_depnum_ccdc_archive 'CCDC 299474'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H15 I2 N O'
_chemical_formula_weight         539.13

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   9.0770(8)
_cell_length_b                   10.3330(9)
_cell_length_c                   10.9250(9)
_cell_angle_alpha                95.4550(10)
_cell_angle_beta                 101.4960(10)
_cell_angle_gamma                106.2000(10)
_cell_volume                     951.82(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    input
_cell_measurement_theta_min      2.403
_cell_measurement_theta_max      28.2615

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    1.881
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             512
_exptl_absorpt_coefficient_mu    3.310
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5573
_exptl_absorpt_correction_T_max  0.7331
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8260
_diffrn_reflns_av_R_equivalents  0.0128
_diffrn_reflns_av_sigmaI/netI    0.0191
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.93
_diffrn_reflns_theta_max         28.29
_reflns_number_total             4336
_reflns_number_gt                4084
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is

not relevant to the choice of reflections for refinement. R-factors based

on F^2^ are statistically about twice as large as those based on F, and R-

factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0187P)^2^+0.6034P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4336
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0188
_refine_ls_R_factor_gt           0.0173
_refine_ls_wR_factor_ref         0.0438
_refine_ls_wR_factor_gt          0.0430
_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
C1 C 0.6867(2) 0.26531(19) 0.24832(17) 0.0170(3) Uani 1 1 d . . .
C2 C 0.5936(2) 0.1490(2) 0.16307(18) 0.0193(4) Uani 1 1 d . . .
H2 H 0.6419 0.0981 0.1157 0.023 Uiso 1 1 calc R . .
C3 C 0.4309(2) 0.1067(2) 0.14662(19) 0.0226(4) Uani 1 1 d . . .
H3 H 0.3685 0.0249 0.0910 0.027 Uiso 1 1 calc R . .
C4 C 0.3594(2) 0.1840(2) 0.21137(19) 0.0228(4) Uani 1 1 d . . .
H4 H 0.2477 0.1569 0.1979 0.027 Uiso 1 1 calc R . .
C5 C 0.4508(2) 0.3004(2) 0.29549(18) 0.0194(4) Uani 1 1 d . . .
H5 H 0.4018 0.3535 0.3396 0.023 Uiso 1 1 calc R . .
C6 C 0.6145(2) 0.34027(18) 0.31585(17) 0.0176(4) Uani 1 1 d . . .
C7 C 0.8352(2) 0.4060(2) 0.0653(2) 0.0241(4) Uani 1 1 d . . .
C8 C 0.8503(3) 0.3096(2) -0.0244(2) 0.0346(5) Uani 1 1 d . . .
H8 H 0.9182 0.2565 -0.0004 0.042 Uiso 1 1 calc R . .
C9 C 0.7676(4) 0.2903(3) -0.1479(3) 0.0560(8) Uani 1 1 d . . .
H9 H 0.7786 0.2238 -0.2088 0.067 Uiso 1 1 calc R . .
C10 C 0.6686(4) 0.3668(5) -0.1840(3) 0.0719(12) Uani 1 1 d . . .
H10 H 0.6109 0.3525 -0.2694 0.086 Uiso 1 1 calc R . .
C11 C 0.6535(4) 0.4643(5) -0.0956(4) 0.0715(12) Uani 1 1 d . . .
H11 H 0.5861 0.5176 -0.1203 0.086 Uiso 1 1 calc R . .
C12 C 0.7372(3) 0.4840(3) 0.0294(3) 0.0441(7) Uani 1 1 d . . .
H12 H 0.7272 0.5511 0.0903 0.053 Uiso 1 1 calc R . .
C13 C 0.8650(2) 0.1140(2) 0.37035(18) 0.0190(4) Uani 1 1 d . . .
C14 C 0.8112(2) 0.1355(2) 0.47923(19) 0.0240(4) Uani 1 1 d . . .
H14 H 0.8263 0.2261 0.5179 0.029 Uiso 1 1 calc R . .
C15 C 0.7360(3) 0.0262(2) 0.5315(2) 0.0306(5) Uani 1 1 d . . .
H15 H 0.6994 0.0417 0.6055 0.037 Uiso 1 1 calc R . .
C16 C 0.7142(3) -0.1056(2) 0.4756(2) 0.0354(5) Uani 1 1 d . . .
H16 H 0.6622 -0.1806 0.5113 0.043 Uiso 1 1 calc R . .
C17 C 0.7676(3) -0.1293(2) 0.3683(2) 0.0298(5) Uani 1 1 d . . .
H17 H 0.7526 -0.2201 0.3303 0.036 Uiso 1 1 calc R . .
C18 C 0.8433(2) -0.0194(2) 0.31640(18) 0.0211(4) Uani 1 1 d . . .
C19 C 0.9468(2) 0.23423(19) 0.31542(18) 0.0189(4) Uani 1 1 d . . .
C20 C 0.9240(2) 0.4242(2) 0.2011(2) 0.0252(4) Uani 1 1 d . . .
H20A H 1.0360 0.4320 0.2042 0.030 Uiso 1 1 calc R . .
H20B H 0.9206 0.5097 0.2479 0.030 Uiso 1 1 calc R . .
I1 I 0.746497(14) 0.506406(12) 0.458577(12) 0.02124(4) Uani 1 1 d . . .
I2 I 0.913197(15) -0.063571(13) 0.149117(12) 0.02448(4) Uani 1 1 d . . .
N1 N 0.85497(18) 0.30757(16) 0.26254(16) 0.0189(3) Uani 1 1 d . . .
O1 O 1.08924(16) 0.26440(15) 0.32117(15) 0.0269(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
C1 0.0145(8) 0.0187(9) 0.0184(9) 0.0059(7) 0.0044(7) 0.0048(7)
C2 0.0190(9) 0.0224(9) 0.0174(9) 0.0016(7) 0.0047(7) 0.0080(7)
C3 0.0189(9) 0.0248(10) 0.0204(9) -0.0013(8) 0.0013(7) 0.0044(8)
C4 0.0139(9) 0.0295(10) 0.0234(10) 0.0020(8) 0.0033(7) 0.0058(8)
C5 0.0189(9) 0.0234(9) 0.0200(9) 0.0056(7) 0.0070(7) 0.0107(7)
C6 0.0186(9) 0.0159(8) 0.0183(9) 0.0037(7) 0.0034(7) 0.0055(7)
C7 0.0216(9) 0.0221(10) 0.0328(11) 0.0122(8) 0.0138(8) 0.0055(8)
C8 0.0450(14) 0.0275(11) 0.0319(12) 0.0075(9) 0.0134(10) 0.0083(10)
C9 0.069(2) 0.0495(17) 0.0296(13) 0.0074(12) 0.0097(13) -0.0118(15)
C10 0.0423(17) 0.110(3) 0.0420(17) 0.044(2) -0.0009(14) -0.0135(18)
C11 0.0406(16) 0.115(3) 0.086(3) 0.081(3) 0.0274(17) 0.0369(19)
C12 0.0420(14) 0.0529(16) 0.0621(18) 0.0387(14) 0.0318(13) 0.0305(13)
C13 0.0148(8) 0.0230(9) 0.0190(9) 0.0014(7) -0.0001(7) 0.0088(7)
C14 0.0242(10) 0.0287(10) 0.0207(9) 0.0005(8) 0.0022(8) 0.0137(8)
C15 0.0377(12) 0.0408(13) 0.0207(10) 0.0092(9) 0.0110(9) 0.0198(10)
C16 0.0467(14) 0.0333(12) 0.0359(13) 0.0173(10) 0.0176(11) 0.0182(11)
C17 0.0377(12) 0.0241(10) 0.0326(11) 0.0088(9) 0.0095(10) 0.0150(9)
C18 0.0203(9) 0.0243(10) 0.0207(9) 0.0019(7) 0.0037(7) 0.0113(8)
C19 0.0168(9) 0.0193(9) 0.0185(9) -0.0055(7) 0.0030(7) 0.0057(7)
C20 0.0234(10) 0.0199(9) 0.0321(11) 0.0060(8) 0.0124(9) 0.0018(8)
I1 0.01977(7) 0.01681(7) 0.02573(7) -0.00200(5) 0.00505(5) 0.00535(5)
I2 0.02541(7) 0.02314(7) 0.02451(7) -0.00327(5) 0.00660(5) 0.00864(5)
N1 0.0144(7) 0.0194(8) 0.0232(8) 0.0030(6) 0.0064(6) 0.0042(6)
O1 0.0142(6) 0.0253(7) 0.0389(9) -0.0045(6) 0.0065(6) 0.0057(5)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate
(isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.390(3) . ?
C1 C6 1.393(3) . ?
C1 N1 1.438(2) . ?
C2 C3 1.387(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(3) . ?
C5 H5 0.9500 . ?
C6 I1 2.1007(19) . ?
C7 C8 1.383(3) . ?
C7 C12 1.385(3) . ?
C7 C20 1.507(3) . ?
C8 C9 1.373(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.379(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.382(6) . ?
C10 H10 0.9500 . ?
C11 C12 1.390(5) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C18 1.390(3) . ?
C13 C14 1.395(3) . ?
C13 C19 1.503(3) . ?
C14 C15 1.384(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.382(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.381(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.388(3) . ?
C17 H17 0.9500 . ?
C18 I2 2.102(2) . ?
C19 O1 1.229(2) . ?
C19 N1 1.359(2) . ?
C20 N1 1.482(2) . ?
C20 H20A 0.9900 . ?
C20 H20B 0.9900 . ?

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
C2 C1 C6 119.23(17) . . ?
C2 C1 N1 119.31(16) . . ?
C6 C1 N1 121.44(17) . . ?
C3 C2 C1 120.49(18) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.97(18) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C5 C4 C3 119.90(18) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.26(17) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 120.07(17) . . ?
C5 C6 I1 118.02(14) . . ?
C1 C6 I1 121.78(13) . . ?
C8 C7 C12 119.5(2) . . ?
C8 C7 C20 119.9(2) . . ?
C12 C7 C20 120.6(2) . . ?
C9 C8 C7 120.4(3) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 120.4(3) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C9 C10 C11 119.8(3) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C10 C11 C12 119.9(3) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C7 C12 C11 120.0(3) . . ?
C7 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C18 C13 C14 118.65(19) . . ?
C18 C13 C19 121.62(17) . . ?
C14 C13 C19 119.72(17) . . ?
C15 C14 C13 120.6(2) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 119.8(2) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C17 C16 C15 120.6(2) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C16 C17 C18 119.4(2) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C17 C18 C13 120.94(19) . . ?
C17 C18 I2 117.22(15) . . ?
C13 C18 I2 121.77(15) . . ?
O1 C19 N1 122.87(18) . . ?
O1 C19 C13 121.05(18) . . ?
N1 C19 C13 116.06(16) . . ?
N1 C20 C7 111.08(16) . . ?
N1 C20 H20A 109.4 . . ?
C7 C20 H20A 109.4 . . ?
N1 C20 H20B 109.4 . . ?
C7 C20 H20B 109.4 . . ?
H20A C20 H20B 108.0 . . ?
C19 N1 C1 122.13(16) . . ?
C19 N1 C20 119.82(16) . . ?
C1 N1 C20 117.51(16) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.9(3) . . . . ?
N1 C1 C2 C3 -179.38(18) . . . . ?
C1 C2 C3 C4 2.8(3) . . . . ?
C2 C3 C4 C5 -2.2(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C4 C5 C6 C1 2.1(3) . . . . ?
C4 C5 C6 I1 -173.76(15) . . . . ?
C2 C1 C6 C5 -1.5(3) . . . . ?
N1 C1 C6 C5 176.88(17) . . . . ?
C2 C1 C6 I1 174.19(14) . . . . ?
N1 C1 C6 I1 -7.4(2) . . . . ?
C12 C7 C8 C9 -0.7(3) . . . . ?
C20 C7 C8 C9 178.7(2) . . . . ?
C7 C8 C9 C10 0.1(4) . . . . ?
C8 C9 C10 C11 0.5(4) . . . . ?
C9 C10 C11 C12 -0.5(5) . . . . ?
C8 C7 C12 C11 0.7(3) . . . . ?
C20 C7 C12 C11 -178.7(2) . . . . ?
C10 C11 C12 C7 -0.1(4) . . . . ?
C18 C13 C14 C15 -0.8(3) . . . . ?
C19 C13 C14 C15 -179.79(18) . . . . ?
C13 C14 C15 C16 0.2(3) . . . . ?
C14 C15 C16 C17 0.3(4) . . . . ?
C15 C16 C17 C18 -0.1(4) . . . . ?
C16 C17 C18 C13 -0.5(3) . . . . ?
C16 C17 C18 I2 -177.67(18) . . . . ?
C14 C13 C18 C17 1.0(3) . . . . ?
C19 C13 C18 C17 179.94(19) . . . . ?
C14 C13 C18 I2 178.00(14) . . . . ?
C19 C13 C18 I2 -3.0(2) . . . . ?
C18 C13 C19 O1 -69.6(3) . . . . ?
C14 C13 C19 O1 109.4(2) . . . . ?
C18 C13 C19 N1 111.8(2) . . . . ?
C14 C13 C19 N1 -69.2(2) . . . . ?
C8 C7 C20 N1 -72.3(2) . . . . ?
C12 C7 C20 N1 107.2(2) . . . . ?
O1 C19 N1 C1 175.38(18) . . . . ?
C13 C19 N1 C1 -6.0(3) . . . . ?
O1 C19 N1 C20 4.1(3) . . . . ?
C13 C19 N1 C20 -177.32(17) . . . . ?
C2 C1 N1 C19 -68.5(2) . . . . ?
C6 C1 N1 C19 113.1(2) . . . . ?
C2 C1 N1 C20 103.0(2) . . . . ?
C6 C1 N1 C20 -75.4(2) . . . . ?
C7 C20 N1 C19 123.03(19) . . . . ?
C7 C20 N1 C1 -48.7(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.918
_diffrn_reflns_theta_full        28.29
_diffrn_measured_fraction_theta_full 0.918
_refine_diff_density_max         0.592
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.074

# Attachment 'Rodrigo 3b.doc'

#Rodrigo 3b = 2186

data_s2186na
_database_code_depnum_ccdc_archive 'CCDC 299475'

_publ_section_exptl_refinement   
;
The structure was solved by direct methods.
The non-hydrogen atoms were refined anisotropically,
except where the ADP becomes NPD or unrealistic.
H atoms were included in calculated positions,
except where they were largely indeterminate.
;

# Insert blank lines between references

_publ_section_references         
;
#
# Put all your general crystallographic references here
# Delete as required from the document CIF
#

Sheldrick, G.M. (1993) SHELXL93. Program for crystal structure
refinement. University of Gottingen, Germany.

Sheldrick, G.M. (1997) SHELXL97. Program for crystal structure
refinement. University of Gottingen, Germany.

Sheldrick, G.M. (1985). SHELXS86. In Crystallographic Computing 3,
edited by G. M. Sheldrick, C. Kruger & R. Goddard, pp. 175-189.
Oxford University Press.

Sheldrick, G.M. (1997) SHELXS97. Program for Crystal Structure solution.
University of Gottingen, Germany.

Wilson, A.J.C. (1992) Ed. International Tables for Crystallography,
Volume C, Kluwer Academic Publishers, Dordrecht, The Netherlands.
;
_publ_section_figure_captions    
;
Figure 1. View of (I) (50% probability displacement ellipsoids)
;
_publ_section_acknowledgements   
;
?
;
_publ_section_table_legends      
;
Table 1. Fractional atomic coordinates and equivalent
isotropic displacement parameters (\%A^2^)

Table 2. Selected geometric parameters (\%A ,\% )
;
#------------------ SECTION 2. COMPOUND(S) DETAILS ------------------------

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H14 I3 N O'
_chemical_formula_weight         665.02

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           Orthorhombic
_symmetry_space_group_name_H-M   Pbcn

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

_cell_length_a                   17.2130(10)
_cell_length_b                   14.9120(8)
_cell_length_c                   15.6580(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4019.1(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    input
_cell_measurement_theta_min      2.6045
_cell_measurement_theta_max      28.2835

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      0
_exptl_crystal_density_diffrn    2.198
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2464
_exptl_absorpt_coefficient_mu    4.674
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.2915
_exptl_absorpt_correction_T_max  0.4550
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            33041
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_sigmaI/netI    0.0161
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.81
_diffrn_reflns_theta_max         28.27
_reflns_number_total             4886
_reflns_number_gt                4675
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is

not relevant to the choice of reflections for refinement. R-factors based

on F^2^ are statistically about twice as large as those based on F, and R-

factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0261P)^2^+9.1515P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4886
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0237
_refine_ls_wR_factor_ref         0.0612
_refine_ls_wR_factor_gt          0.0603
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_restrained_S_all      1.138
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.66108(16) 0.15937(19) 0.96707(16) 0.0137(5) Uani 1 1 d . . .
C2 C 0.69037(16) 0.07193(19) 0.96855(17) 0.0153(5) Uani 1 1 d . . .
C3 C 0.76975(17) 0.0567(2) 0.97735(19) 0.0201(6) Uani 1 1 d . . .
H3 H 0.7895 -0.0028 0.9773 0.024 Uiso 1 1 calc R . .
C4 C 0.81978(17) 0.1292(2) 0.9862(2) 0.0210(6) Uani 1 1 d . . .
H4 H 0.8740 0.1192 0.9924 0.025 Uiso 1 1 calc R . .
C5 C 0.79101(17) 0.2162(2) 0.98591(18) 0.0188(6) Uani 1 1 d . . .
H5 H 0.8254 0.2655 0.9930 0.023 Uiso 1 1 calc R . .
C6 C 0.71220(16) 0.23113(19) 0.97529(17) 0.0163(5) Uani 1 1 d . . .
H6 H 0.6929 0.2908 0.9736 0.020 Uiso 1 1 calc R . .
C7 C 0.55250(17) 0.1742(2) 0.86438(18) 0.0184(6) Uani 1 1 d . . .
H7A H 0.4953 0.1815 0.8631 0.022 Uiso 1 1 calc R . .
H7B H 0.5653 0.1155 0.8384 0.022 Uiso 1 1 calc R . .
C8 C 0.59022(18) 0.2484(2) 0.81341(18) 0.0198(6) Uani 1 1 d . . .
C9 C 0.64867(18) 0.2357(2) 0.75321(19) 0.0215(6) Uani 1 1 d . . .
C10 C 0.6846(2) 0.3075(2) 0.7120(2) 0.0276(7) Uani 1 1 d . . .
H10 H 0.7243 0.2973 0.6711 0.033 Uiso 1 1 calc R . .
C11 C 0.6613(2) 0.3942(2) 0.7318(2) 0.0335(8) Uani 1 1 d . . .
H11 H 0.6851 0.4439 0.7043 0.040 Uiso 1 1 calc R . .
C12 C 0.6036(2) 0.4077(2) 0.7915(3) 0.0341(8) Uani 1 1 d . . .
H12 H 0.5882 0.4671 0.8054 0.041 Uiso 1 1 calc R . .
C13 C 0.5681(2) 0.3364(2) 0.8311(2) 0.0271(7) Uani 1 1 d . . .
H13 H 0.5278 0.3473 0.8712 0.033 Uiso 1 1 calc R . .
C14 C 0.53328(16) 0.21090(18) 1.01561(18) 0.0149(5) Uani 1 1 d . . .
C15 C 0.56647(15) 0.2158(2) 1.10425(18) 0.0153(5) Uani 1 1 d . . .
C16 C 0.57571(16) 0.29743(19) 1.14622(19) 0.0178(5) Uani 1 1 d . . .
C17 C 0.60014(19) 0.3006(2) 1.2312(2) 0.0237(6) Uani 1 1 d . . .
H17 H 0.6071 0.3567 1.2590 0.028 Uiso 1 1 calc R . .
C18 C 0.61398(19) 0.2217(2) 1.2745(2) 0.0262(7) Uani 1 1 d . . .
H18 H 0.6300 0.2235 1.3326 0.031 Uiso 1 1 calc R . .
C19 C 0.60475(19) 0.1396(2) 1.2340(2) 0.0248(6) Uani 1 1 d . . .
H19 H 0.6142 0.0855 1.2642 0.030 Uiso 1 1 calc R . .
C20 C 0.58158(17) 0.1370(2) 1.14921(18) 0.0187(5) Uani 1 1 d . . .
H20 H 0.5759 0.0808 1.1214 0.022 Uiso 1 1 calc R . .
I1 I 0.616484(11) -0.039195(12) 0.962300(12) 0.01879(6) Uani 1 1 d . . .
I2 I 0.687428(14) 0.107799(16) 0.718615(15) 0.03325(7) Uani 1 1 d . . .
I3 I 0.555874(12) 0.420112(13) 1.083930(14) 0.02372(6) Uani 1 1 d . . .
N1 N 0.57999(14) 0.17608(16) 0.95376(14) 0.0144(4) Uani 1 1 d . . .
O1 O 0.46630(12) 0.23373(15) 1.00222(14) 0.0220(4) 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
C1 0.0122(12) 0.0177(13) 0.0111(11) 0.0007(9) 0.0009(9) 0.0017(10)
C2 0.0148(13) 0.0156(13) 0.0154(13) -0.0011(10) -0.0017(10) -0.0011(10)
C3 0.0164(14) 0.0189(14) 0.0250(14) 0.0001(11) -0.0006(11) 0.0039(11)
C4 0.0131(13) 0.0261(15) 0.0239(14) 0.0016(12) -0.0011(11) 0.0017(11)
C5 0.0161(13) 0.0216(14) 0.0189(13) 0.0015(11) -0.0003(11) -0.0039(11)
C6 0.0168(13) 0.0169(13) 0.0151(12) 0.0016(10) 0.0011(10) -0.0007(11)
C7 0.0155(13) 0.0229(14) 0.0168(13) -0.0011(11) -0.0050(10) 0.0003(11)
C8 0.0199(14) 0.0242(15) 0.0152(13) 0.0020(11) -0.0065(11) 0.0019(11)
C9 0.0214(15) 0.0264(15) 0.0166(13) -0.0006(12) -0.0049(11) 0.0005(12)
C10 0.0268(16) 0.0354(18) 0.0206(15) 0.0076(13) -0.0002(12) -0.0016(14)
C11 0.039(2) 0.0314(18) 0.0305(18) 0.0141(14) -0.0014(15) -0.0013(15)
C12 0.040(2) 0.0228(16) 0.039(2) 0.0015(14) 0.0001(16) 0.0049(14)
C13 0.0294(17) 0.0287(17) 0.0233(15) 0.0048(13) -0.0022(13) 0.0091(13)
C14 0.0128(12) 0.0119(12) 0.0201(13) 0.0003(10) 0.0006(10) -0.0024(10)
C15 0.0109(12) 0.0197(14) 0.0154(12) -0.0006(10) 0.0030(10) 0.0004(10)
C16 0.0147(13) 0.0171(13) 0.0217(14) -0.0017(11) 0.0028(10) -0.0011(10)
C17 0.0226(15) 0.0258(15) 0.0228(15) -0.0090(12) 0.0020(12) 0.0000(12)
C18 0.0274(16) 0.0348(18) 0.0163(14) -0.0035(12) 0.0002(12) 0.0005(13)
C19 0.0279(16) 0.0270(16) 0.0195(14) 0.0037(12) 0.0025(12) 0.0035(13)
C20 0.0204(14) 0.0175(13) 0.0182(13) -0.0008(11) 0.0037(11) 0.0004(11)
I1 0.01898(10) 0.01481(9) 0.02258(10) -0.00301(7) -0.00127(7) -0.00249(6)
I2 0.03637(13) 0.02955(12) 0.03384(13) -0.00770(9) 0.00792(9) 0.00024(9)
I3 0.02501(11) 0.01512(10) 0.03103(11) -0.00072(7) 0.00022(8) -0.00120(7)
N1 0.0120(11) 0.0173(11) 0.0138(10) -0.0001(9) -0.0023(8) 0.0002(9)
O1 0.0137(10) 0.0249(11) 0.0273(11) -0.0035(9) -0.0003(8) 0.0026(8)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate
(isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.391(4) . ?
C1 C2 1.398(4) . ?
C1 N1 1.433(3) . ?
C2 C3 1.392(4) . ?
C2 I1 2.091(3) . ?
C3 C4 1.389(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.389(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(4) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N1 1.478(3) . ?
C7 C8 1.512(4) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.392(4) . ?
C8 C13 1.394(5) . ?
C9 C10 1.395(5) . ?
C9 I2 2.091(3) . ?
C10 C11 1.387(5) . ?
C10 H10 0.9500 . ?
C11 C12 1.379(6) . ?
C11 H11 0.9500 . ?
C12 C13 1.374(5) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C14 O1 1.220(3) . ?
C14 N1 1.362(4) . ?
C14 C15 1.503(4) . ?
C15 C16 1.392(4) . ?
C15 C20 1.395(4) . ?
C16 C17 1.397(4) . ?
C16 I3 2.101(3) . ?
C17 C18 1.379(5) . ?
C17 H17 0.9500 . ?
C18 C19 1.387(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.387(4) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?

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
C6 C1 C2 119.2(3) . . ?
C6 C1 N1 119.7(2) . . ?
C2 C1 N1 121.0(2) . . ?
C3 C2 C1 120.5(3) . . ?
C3 C2 I1 118.2(2) . . ?
C1 C2 I1 121.3(2) . . ?
C4 C3 C2 119.4(3) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C5 C4 C3 120.4(3) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C6 C5 C4 120.0(3) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C1 120.5(3) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
N1 C7 C8 110.4(2) . . ?
N1 C7 H7A 109.6 . . ?
C8 C7 H7A 109.6 . . ?
N1 C7 H7B 109.6 . . ?
C8 C7 H7B 109.6 . . ?
H7A C7 H7B 108.1 . . ?
C9 C8 C13 117.4(3) . . ?
C9 C8 C7 124.6(3) . . ?
C13 C8 C7 117.9(3) . . ?
C8 C9 C10 121.9(3) . . ?
C8 C9 I2 122.1(2) . . ?
C10 C9 I2 116.1(2) . . ?
C11 C10 C9 119.0(3) . . ?
C11 C10 H10 120.5 . . ?
C9 C10 H10 120.5 . . ?
C12 C11 C10 119.6(3) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
C13 C12 C11 120.9(3) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C8 121.2(3) . . ?
C12 C13 H13 119.4 . . ?
C8 C13 H13 119.4 . . ?
O1 C14 N1 122.8(3) . . ?
O1 C14 C15 120.3(3) . . ?
N1 C14 C15 116.8(2) . . ?
C16 C15 C20 118.5(3) . . ?
C16 C15 C14 121.5(3) . . ?
C20 C15 C14 119.7(3) . . ?
C15 C16 C17 120.9(3) . . ?
C15 C16 I3 121.6(2) . . ?
C17 C16 I3 117.5(2) . . ?
C18 C17 C16 119.4(3) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 C19 120.6(3) . . ?
C17 C18 H18 119.7 . . ?
C19 C18 H18 119.7 . . ?
C20 C19 C18 119.7(3) . . ?
C20 C19 H19 120.1 . . ?
C18 C19 H19 120.1 . . ?
C19 C20 C15 120.9(3) . . ?
C19 C20 H20 119.6 . . ?
C15 C20 H20 119.6 . . ?
C14 N1 C1 122.6(2) . . ?
C14 N1 C7 119.5(2) . . ?
C1 N1 C7 116.5(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.6(4) . . . . ?
N1 C1 C2 C3 176.8(3) . . . . ?
C6 C1 C2 I1 177.10(19) . . . . ?
N1 C1 C2 I1 -5.5(4) . . . . ?
C1 C2 C3 C4 1.1(4) . . . . ?
I1 C2 C3 C4 -176.6(2) . . . . ?
C2 C3 C4 C5 -0.3(5) . . . . ?
C3 C4 C5 C6 -1.1(5) . . . . ?
C4 C5 C6 C1 1.7(4) . . . . ?
C2 C1 C6 C5 -0.8(4) . . . . ?
N1 C1 C6 C5 -178.3(2) . . . . ?
N1 C7 C8 C9 106.2(3) . . . . ?
N1 C7 C8 C13 -70.1(3) . . . . ?
C13 C8 C9 C10 0.4(4) . . . . ?
C7 C8 C9 C10 -175.9(3) . . . . ?
C13 C8 C9 I2 -179.3(2) . . . . ?
C7 C8 C9 I2 4.4(4) . . . . ?
C8 C9 C10 C11 0.1(5) . . . . ?
I2 C9 C10 C11 179.7(3) . . . . ?
C9 C10 C11 C12 0.1(5) . . . . ?
C10 C11 C12 C13 -0.8(6) . . . . ?
C11 C12 C13 C8 1.2(6) . . . . ?
C9 C8 C13 C12 -1.0(5) . . . . ?
C7 C8 C13 C12 175.6(3) . . . . ?
O1 C14 C15 C16 -64.4(4) . . . . ?
N1 C14 C15 C16 118.8(3) . . . . ?
O1 C14 C15 C20 109.3(3) . . . . ?
N1 C14 C15 C20 -67.5(3) . . . . ?
C20 C15 C16 C17 0.5(4) . . . . ?
C14 C15 C16 C17 174.3(3) . . . . ?
C20 C15 C16 I3 179.2(2) . . . . ?
C14 C15 C16 I3 -7.0(4) . . . . ?
C15 C16 C17 C18 -1.1(5) . . . . ?
I3 C16 C17 C18 -179.9(2) . . . . ?
C16 C17 C18 C19 0.8(5) . . . . ?
C17 C18 C19 C20 0.2(5) . . . . ?
C18 C19 C20 C15 -0.8(5) . . . . ?
C16 C15 C20 C19 0.5(4) . . . . ?
C14 C15 C20 C19 -173.4(3) . . . . ?
O1 C14 N1 C1 172.4(3) . . . . ?
C15 C14 N1 C1 -10.9(4) . . . . ?
O1 C14 N1 C7 6.7(4) . . . . ?
C15 C14 N1 C7 -176.5(2) . . . . ?
C6 C1 N1 C14 -69.8(3) . . . . ?
C2 C1 N1 C14 112.8(3) . . . . ?
C6 C1 N1 C7 96.2(3) . . . . ?
C2 C1 N1 C7 -81.2(3) . . . . ?
C8 C7 N1 C14 102.6(3) . . . . ?
C8 C7 N1 C1 -63.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.981
_diffrn_reflns_theta_full        28.27
_diffrn_measured_fraction_theta_full 0.981
_refine_diff_density_max         0.980
_refine_diff_density_min         -1.149
_refine_diff_density_rms         0.111


# Attachment 'Rodrigo 7b.doc'

data_s2118abs
_database_code_depnum_ccdc_archive 'CCDC 299476'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
#---------------------------------------------------------------------------

_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H20 Cl2 I2 N2 O2'
_chemical_formula_weight         681.11

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   7.984(5)
_cell_length_b                   24.878(5)
_cell_length_c                   12.520(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 98.498(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     2459.5(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7131
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      26.33

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.839
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1312
_exptl_absorpt_coefficient_mu    2.797
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5415
_exptl_absorpt_correction_T_max  0.7673
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71069
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14331
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_sigmaI/netI    0.0371
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.64
_diffrn_reflns_theta_max         26.35
_reflns_number_total             6811
_reflns_number_gt                6583
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SIR-97 (Altomare, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is

not relevant to the choice of reflections for refinement. R-factors based

on F^2^ are statistically about twice as large as those based on F, and R-

factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0466P)^2^+10.8042P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.03(2)
_refine_ls_number_reflns         6811
_refine_ls_number_parameters     563
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0411
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.0987
_refine_ls_wR_factor_gt          0.0977
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.004
_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 0.55500(6) 0.83098(2) 0.41315(3) 0.01936(11) Uani 1 1 d . . .
I2 I 0.37756(7) 0.44119(2) 0.29774(5) 0.03159(14) Uani 1 1 d . . .
O1 O 0.4386(6) 0.7086(2) 0.2317(4) 0.0173(11) Uani 1 1 d . . .
O2 O 0.6215(6) 0.5620(2) 0.4313(4) 0.0172(11) Uani 1 1 d . . .
N1 N 0.5310(7) 0.6842(3) 0.4037(4) 0.0120(12) Uani 1 1 d . . .
N2 N 0.4158(7) 0.5854(3) 0.2939(4) 0.0111(12) Uani 1 1 d . . .
C1 C 0.7424(9) 0.7894(3) 0.3446(5) 0.0170(15) Uani 1 1 d . . .
C2 C 0.7151(9) 0.7376(3) 0.3068(5) 0.0151(14) Uani 1 1 d . . .
C3 C 0.8437(9) 0.7115(3) 0.2623(5) 0.0167(15) Uani 1 1 d . . .
H3 H 0.8257 0.6760 0.2350 0.020 Uiso 1 1 calc R . .
C4 C 0.9971(9) 0.7368(4) 0.2576(6) 0.0231(17) Uani 1 1 d . . .
H4 H 1.0850 0.7184 0.2292 0.028 Uiso 1 1 calc R . .
C5 C 1.0215(10) 0.7894(4) 0.2949(6) 0.0259(18) Uani 1 1 d . . .
H5 H 1.1260 0.8071 0.2912 0.031 Uiso 1 1 calc R . .
C6 C 0.8941(10) 0.8161(3) 0.3373(6) 0.0237(18) Uani 1 1 d . . .
H6 H 0.9098 0.8522 0.3612 0.028 Uiso 1 1 calc R . .
C7 C 0.5493(8) 0.7089(3) 0.3092(5) 0.0118(13) Uani 1 1 d . . .
C8 C 0.6604(8) 0.6860(3) 0.5032(5) 0.0131(14) Uani 1 1 d . . .
H8A H 0.7695 0.6974 0.4839 0.020 Uiso 1 1 calc R . .
H8B H 0.6723 0.6501 0.5360 0.020 Uiso 1 1 calc R . .
H8C H 0.6243 0.7115 0.5548 0.020 Uiso 1 1 calc R . .
C9 C 0.3714(8) 0.6600(3) 0.4161(5) 0.0129(14) Uani 1 1 d . . .
C10 C 0.3174(8) 0.6127(3) 0.3647(5) 0.0140(14) Uani 1 1 d . . .
C11 C 0.1616(8) 0.5905(3) 0.3787(5) 0.0136(14) Uani 1 1 d . . .
H11 H 0.1235 0.5583 0.3422 0.016 Uiso 1 1 calc R . .
C12 C 0.0626(8) 0.6157(3) 0.4460(5) 0.0172(15) Uani 1 1 d . . .
H12 H -0.0437 0.6008 0.4555 0.021 Uiso 1 1 calc R . .
C13 C 0.1194(9) 0.6630(3) 0.4998(5) 0.0167(15) Uani 1 1 d . . .
H13 H 0.0528 0.6798 0.5470 0.020 Uiso 1 1 calc R . .
C14 C 0.2725(8) 0.6851(3) 0.4842(6) 0.0142(14) Uani 1 1 d . . .
H14 H 0.3104 0.7175 0.5199 0.017 Uiso 1 1 calc R . .
C15 C 0.3376(9) 0.5815(3) 0.1820(5) 0.0163(15) Uani 1 1 d . . .
H15A H 0.2395 0.5575 0.1766 0.024 Uiso 1 1 calc R . .
H15B H 0.4198 0.5672 0.1385 0.024 Uiso 1 1 calc R . .
H15C H 0.3007 0.6173 0.1553 0.024 Uiso 1 1 calc R . .
C16 C 0.5575(8) 0.5594(3) 0.3361(5) 0.0122(13) Uani 1 1 d . . .
C17 C 0.6394(9) 0.5245(3) 0.2583(5) 0.0146(14) Uani 1 1 d . . .
C18 C 0.5854(10) 0.4733(4) 0.2327(7) 0.0231(17) Uani 1 1 d . . .
C19 C 0.6680(10) 0.4407(4) 0.1679(7) 0.0288(18) Uani 1 1 d . . .
H19 H 0.6308 0.4048 0.1532 0.035 Uiso 1 1 calc R . .
C20 C 0.8052(10) 0.4605(4) 0.1243(6) 0.0265(19) Uani 1 1 d . . .
H20 H 0.8615 0.4385 0.0788 0.032 Uiso 1 1 calc R . .
C21 C 0.8604(10) 0.5132(4) 0.1477(6) 0.0239(17) Uani 1 1 d . . .
H21 H 0.9538 0.5272 0.1176 0.029 Uiso 1 1 calc R . .
C22 C 0.7787(8) 0.5444(3) 0.2144(5) 0.0157(14) Uani 1 1 d . . .
H22 H 0.8171 0.5800 0.2310 0.019 Uiso 1 1 calc R . .
I3 I 0.22741(8) 0.44641(3) 0.94293(5) 0.03724(16) Uani 1 1 d . . .
I4 I -0.04049(7) 0.82743(3) 0.68021(7) 0.0499(2) Uani 1 1 d . . .
O3 O 0.1698(6) 0.5819(2) 0.9551(4) 0.0194(11) Uani 1 1 d . . .
O4 O -0.0832(6) 0.6937(2) 0.7153(4) 0.0174(11) Uani 1 1 d . . .
N3 N -0.0434(7) 0.5834(3) 0.8139(4) 0.0135(12) Uani 1 1 d . . .
N4 N 0.0246(7) 0.6914(3) 0.8935(5) 0.0141(12) Uani 1 1 d . . .
C23 C 0.2970(10) 0.4928(3) 0.8156(6) 0.0192(15) Uani 1 1 d . . .
C24 C 0.2303(9) 0.5430(3) 0.7916(5) 0.0162(14) Uani 1 1 d . . .
C25 C 0.2783(9) 0.5716(3) 0.7053(5) 0.0190(15) Uani 1 1 d . . .
H25 H 0.2331 0.6064 0.6885 0.023 Uiso 1 1 calc R . .
C26 C 0.3934(9) 0.5491(4) 0.6430(6) 0.0217(17) Uani 1 1 d . . .
H26 H 0.4264 0.5684 0.5842 0.026 Uiso 1 1 calc R . .
C27 C 0.4579(9) 0.4982(4) 0.6689(6) 0.0231(17) Uani 1 1 d . . .
H27 H 0.5356 0.4827 0.6271 0.028 Uiso 1 1 calc R . .
C28 C 0.4110(10) 0.4696(4) 0.7545(6) 0.0243(17) Uani 1 1 d . . .
H28 H 0.4556 0.4348 0.7715 0.029 Uiso 1 1 calc R . .
C29 C 0.1148(9) 0.5706(3) 0.8605(5) 0.0151(14) Uani 1 1 d . . .
C30 C -0.1180(9) 0.5644(4) 0.7047(6) 0.0220(17) Uani 1 1 d . . .
H30A H -0.1754 0.5300 0.7109 0.033 Uiso 1 1 calc R . .
H30B H -0.0279 0.5597 0.6601 0.033 Uiso 1 1 calc R . .
H30C H -0.1998 0.5910 0.6710 0.033 Uiso 1 1 calc R . .
C31 C -0.1532(8) 0.6095(3) 0.8773(5) 0.0128(14) Uani 1 1 d . . .
C32 C -0.1190(8) 0.6614(3) 0.9170(5) 0.0116(13) Uani 1 1 d . . .
C33 C -0.2261(9) 0.6846(3) 0.9826(5) 0.0153(15) Uani 1 1 d . . .
H33 H -0.2006 0.7193 1.0127 0.018 Uiso 1 1 calc R . .
C34 C -0.3705(9) 0.6575(4) 1.0041(5) 0.0189(16) Uani 1 1 d . . .
H34 H -0.4432 0.6736 1.0485 0.023 Uiso 1 1 calc R . .
C35 C -0.4075(9) 0.6069(4) 0.9606(6) 0.0221(17) Uani 1 1 d . . .
H35 H -0.5069 0.5886 0.9736 0.026 Uiso 1 1 calc R . .
C36 C -0.2979(9) 0.5830(4) 0.8976(6) 0.0198(16) Uani 1 1 d . . .
H36 H -0.3228 0.5482 0.8684 0.024 Uiso 1 1 calc R . .
C37 C 0.1415(10) 0.7120(4) 0.9849(6) 0.0230(17) Uani 1 1 d . . .
H37A H 0.2413 0.7272 0.9590 0.034 Uiso 1 1 calc R . .
H37B H 0.1767 0.6826 1.0354 0.034 Uiso 1 1 calc R . .
H37C H 0.0852 0.7399 1.0218 0.034 Uiso 1 1 calc R . .
C38 C 0.0288(9) 0.7052(3) 0.7883(6) 0.0161(15) Uani 1 1 d . . .
C39 C 0.1876(9) 0.7326(3) 0.7640(5) 0.0148(14) Uani 1 1 d . . .
C40 C 0.1831(9) 0.7826(3) 0.7130(6) 0.0206(16) Uani 1 1 d . . .
C41 C 0.3285(9) 0.8051(4) 0.6846(6) 0.0225(16) Uani 1 1 d . . .
H41 H 0.3243 0.8397 0.6521 0.027 Uiso 1 1 calc R . .
C42 C 0.4806(9) 0.7773(4) 0.7035(6) 0.0222(17) Uani 1 1 d . . .
H42 H 0.5798 0.7927 0.6826 0.027 Uiso 1 1 calc R . .
C43 C 0.4887(9) 0.7277(3) 0.7524(6) 0.0169(15) Uani 1 1 d . . .
H43 H 0.5929 0.7086 0.7650 0.020 Uiso 1 1 calc R . .
C44 C 0.3424(9) 0.7055(3) 0.7836(5) 0.0152(14) Uani 1 1 d . . .
H44 H 0.3483 0.6715 0.8185 0.018 Uiso 1 1 calc R . .
Cl1 Cl 0.2774(3) 0.85973(11) 0.09931(18) 0.0385(5) Uani 1 1 d . . .
Cl2 Cl 0.5128(3) 0.80884(9) -0.02763(16) 0.0299(4) Uani 1 1 d . . .
C1S C 0.4651(11) 0.8222(4) 0.1034(6) 0.031(2) Uani 1 1 d . . .
H1S1 H 0.4530 0.7878 0.1412 0.037 Uiso 1 1 calc R . .
H1S2 H 0.5600 0.8423 0.1450 0.037 Uiso 1 1 calc R . .
Cl3 Cl 0.7819(3) 0.41252(11) 0.5568(3) 0.0478(7) Uani 1 1 d . . .
Cl4 Cl 1.0884(3) 0.46450(9) 0.51445(17) 0.0287(4) Uani 1 1 d . . .
C2S C 0.8732(10) 0.4539(4) 0.4681(7) 0.030(2) Uani 1 1 d . . .
H2S1 H 0.8135 0.4889 0.4611 0.036 Uiso 1 1 calc R . .
H2S2 H 0.8602 0.4369 0.3958 0.036 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 0.0240(2) 0.0142(2) 0.0208(2) -0.0020(2) 0.00629(15) 0.0016(2)
I2 0.0313(3) 0.0146(3) 0.0538(3) 0.0014(3) 0.0227(2) -0.0040(2)
O1 0.016(2) 0.017(3) 0.019(2) 0.002(2) 0.0025(19) -0.001(2)
O2 0.018(2) 0.021(3) 0.013(2) 0.001(2) 0.0026(18) 0.002(2)
N1 0.011(3) 0.013(3) 0.012(3) 0.001(2) 0.002(2) -0.001(2)
N2 0.017(3) 0.012(3) 0.005(2) 0.000(2) 0.0030(19) -0.001(2)
C1 0.016(3) 0.023(4) 0.012(3) -0.001(3) 0.005(2) -0.002(3)
C2 0.019(3) 0.011(4) 0.017(3) 0.005(3) 0.007(3) -0.002(3)
C3 0.019(3) 0.016(4) 0.016(3) 0.001(3) 0.006(3) 0.002(3)
C4 0.019(4) 0.031(5) 0.019(3) 0.002(3) 0.003(3) -0.004(3)
C5 0.022(4) 0.033(5) 0.025(4) 0.002(4) 0.011(3) -0.014(4)
C6 0.033(4) 0.015(4) 0.024(4) 0.000(3) 0.011(3) -0.015(3)
C7 0.014(3) 0.011(4) 0.011(3) 0.000(3) 0.006(2) 0.004(3)
C8 0.009(3) 0.020(4) 0.010(3) 0.003(3) 0.000(2) 0.000(3)
C9 0.006(3) 0.023(4) 0.009(3) 0.005(3) -0.001(2) -0.004(3)
C10 0.010(3) 0.019(4) 0.012(3) 0.004(3) 0.001(2) -0.001(3)
C11 0.014(3) 0.012(4) 0.015(3) 0.003(3) -0.001(2) -0.002(3)
C12 0.010(3) 0.028(4) 0.014(3) 0.004(3) 0.001(2) 0.000(3)
C13 0.017(3) 0.022(4) 0.011(3) 0.001(3) 0.001(2) 0.010(3)
C14 0.011(3) 0.016(4) 0.016(3) 0.001(3) 0.000(2) 0.003(3)
C15 0.016(3) 0.016(4) 0.016(3) -0.003(3) 0.001(3) 0.003(3)
C16 0.010(3) 0.010(3) 0.016(3) 0.002(3) 0.001(2) -0.001(3)
C17 0.017(3) 0.014(4) 0.012(3) -0.003(3) 0.001(2) 0.002(3)
C18 0.021(4) 0.019(4) 0.031(4) -0.003(3) 0.007(3) 0.002(3)
C19 0.028(4) 0.021(4) 0.037(4) -0.012(4) 0.001(3) 0.001(4)
C20 0.025(4) 0.033(5) 0.023(4) -0.012(4) 0.008(3) 0.005(4)
C21 0.018(4) 0.027(5) 0.028(4) -0.001(4) 0.008(3) -0.001(3)
C22 0.014(3) 0.018(4) 0.015(3) -0.003(3) 0.003(2) -0.002(3)
I3 0.0542(4) 0.0242(3) 0.0378(3) 0.0140(3) 0.0220(3) 0.0096(3)
I4 0.0188(2) 0.0238(3) 0.1076(6) 0.0264(4) 0.0111(3) 0.0051(3)
O3 0.018(2) 0.024(3) 0.015(2) -0.004(2) -0.0004(18) 0.008(2)
O4 0.016(2) 0.023(3) 0.013(2) 0.002(2) 0.0019(19) -0.005(2)
N3 0.014(3) 0.014(3) 0.013(3) -0.002(2) 0.003(2) 0.002(2)
N4 0.011(3) 0.015(3) 0.017(3) 0.005(2) 0.004(2) -0.003(2)
C23 0.025(4) 0.020(4) 0.013(3) -0.001(3) 0.004(3) -0.001(3)
C24 0.020(3) 0.016(4) 0.012(3) -0.002(3) 0.002(3) 0.004(3)
C25 0.023(4) 0.021(4) 0.012(3) 0.003(3) 0.002(3) -0.004(3)
C26 0.021(4) 0.031(5) 0.014(3) -0.006(3) 0.003(3) 0.000(3)
C27 0.018(3) 0.031(5) 0.020(4) -0.008(3) 0.001(3) 0.003(3)
C28 0.027(4) 0.022(4) 0.023(4) -0.003(3) 0.003(3) 0.009(4)
C29 0.023(4) 0.009(4) 0.014(3) 0.002(3) 0.003(3) 0.001(3)
C30 0.012(3) 0.028(5) 0.026(4) -0.008(3) 0.003(3) -0.002(3)
C31 0.014(3) 0.015(4) 0.009(3) 0.002(3) 0.001(2) 0.001(3)
C32 0.011(3) 0.015(4) 0.009(3) 0.004(3) 0.003(2) 0.004(3)
C33 0.016(3) 0.019(4) 0.012(3) -0.001(3) 0.008(3) 0.004(3)
C34 0.015(3) 0.028(5) 0.014(3) 0.003(3) 0.002(2) 0.006(3)
C35 0.017(3) 0.036(5) 0.014(3) 0.007(3) 0.004(3) 0.004(3)
C36 0.016(3) 0.027(5) 0.017(3) 0.002(3) 0.002(3) -0.006(3)
C37 0.025(4) 0.029(5) 0.015(3) -0.008(3) 0.004(3) -0.010(4)
C38 0.019(3) 0.012(4) 0.019(3) 0.001(3) 0.009(3) 0.000(3)
C39 0.018(3) 0.013(4) 0.014(3) 0.000(3) 0.005(2) -0.002(3)
C40 0.013(3) 0.016(4) 0.033(4) 0.005(3) 0.004(3) 0.004(3)
C41 0.022(4) 0.016(4) 0.028(4) 0.007(3) 0.001(3) -0.001(3)
C42 0.021(4) 0.030(5) 0.016(3) -0.003(3) 0.004(3) -0.006(3)
C43 0.010(3) 0.024(4) 0.015(3) -0.005(3) -0.001(2) -0.001(3)
C44 0.014(3) 0.015(4) 0.015(3) -0.001(3) -0.002(3) 0.002(3)
Cl1 0.0415(12) 0.0393(14) 0.0365(11) 0.0082(10) 0.0118(9) 0.0056(11)
Cl2 0.0420(11) 0.0213(10) 0.0257(9) -0.0034(8) 0.0031(8) -0.0002(9)
C1S 0.049(5) 0.025(5) 0.019(4) 0.011(4) 0.004(3) -0.001(4)
Cl3 0.0252(11) 0.0266(13) 0.095(2) 0.0079(13) 0.0210(12) 0.0006(9)
Cl4 0.0281(10) 0.0265(11) 0.0328(10) -0.0013(9) 0.0084(8) -0.0083(9)
C2S 0.026(4) 0.029(5) 0.032(4) -0.003(4) -0.011(3) 0.009(4)

_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate
(isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.104(7) . ?
I2 C18 2.110(8) . ?
O1 C7 1.212(8) . ?
O2 C16 1.227(8) . ?
N1 C7 1.361(9) . ?
N1 C9 1.438(8) . ?
N1 C8 1.496(8) . ?
N2 C16 1.342(9) . ?
N2 C10 1.439(9) . ?
N2 C15 1.450(8) . ?
C1 C2 1.377(11) . ?
C1 C6 1.396(10) . ?
C2 C3 1.399(10) . ?
C2 C7 1.508(10) . ?
C3 C4 1.386(10) . ?
C3 H3 0.9500 . ?
C4 C5 1.394(13) . ?
C4 H4 0.9500 . ?
C5 C6 1.383(12) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 C10 1.379(11) . ?
C9 C14 1.392(10) . ?
C10 C11 1.396(10) . ?
C11 C12 1.387(10) . ?
C11 H11 0.9500 . ?
C12 C13 1.398(11) . ?
C12 H12 0.9500 . ?
C13 C14 1.381(10) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.523(9) . ?
C17 C18 1.368(11) . ?
C17 C22 1.402(10) . ?
C18 C19 1.382(12) . ?
C19 C20 1.384(12) . ?
C19 H19 0.9500 . ?
C20 C21 1.400(13) . ?
C20 H20 0.9500 . ?
C21 C22 1.374(11) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
I3 C23 2.108(8) . ?
I4 C40 2.093(7) . ?
O3 C29 1.233(9) . ?
O4 C38 1.215(9) . ?
N3 C29 1.348(9) . ?
N3 C31 1.423(9) . ?
N3 C30 1.486(9) . ?
N4 C38 1.367(9) . ?
N4 C32 1.435(9) . ?
N4 C37 1.458(9) . ?
C23 C24 1.374(11) . ?
C23 C28 1.396(11) . ?
C24 C25 1.393(10) . ?
C24 C29 1.517(10) . ?
C25 C26 1.405(10) . ?
C25 H25 0.9500 . ?
C26 C27 1.388(13) . ?
C26 H26 0.9500 . ?
C27 C28 1.383(12) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 C36 1.386(10) . ?
C31 C32 1.395(10) . ?
C32 C33 1.395(9) . ?
C33 C34 1.397(10) . ?
C33 H33 0.9500 . ?
C34 C35 1.384(12) . ?
C34 H34 0.9500 . ?
C35 C36 1.394(11) . ?
C35 H35 0.9500 . ?
C36 H36 0.9500 . ?
C37 H37A 0.9800 . ?
C37 H37B 0.9800 . ?
C37 H37C 0.9800 . ?
C38 C39 1.510(10) . ?
C39 C40 1.396(11) . ?
C39 C44 1.398(10) . ?
C40 C41 1.381(11) . ?
C41 C42 1.387(11) . ?
C41 H41 0.9500 . ?
C42 C43 1.376(12) . ?
C42 H42 0.9500 . ?
C43 C44 1.399(10) . ?
C43 H43 0.9500 . ?
C44 H44 0.9500 . ?
Cl1 C1S 1.760(9) . ?
Cl2 C1S 1.770(8) . ?
C1S H1S1 0.9900 . ?
C1S H1S2 0.9900 . ?
Cl3 C2S 1.749(10) . ?
Cl4 C2S 1.750(8) . ?
C2S H2S1 0.9900 . ?
C2S H2S2 0.9900 . ?

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
C7 N1 C9 119.6(6) . . ?
C7 N1 C8 124.1(6) . . ?
C9 N1 C8 115.9(5) . . ?
C16 N2 C10 119.4(5) . . ?
C16 N2 C15 124.4(6) . . ?
C10 N2 C15 115.5(5) . . ?
C2 C1 C6 121.1(7) . . ?
C2 C1 I1 120.9(5) . . ?
C6 C1 I1 118.0(6) . . ?
C1 C2 C3 118.9(7) . . ?
C1 C2 C7 122.1(6) . . ?
C3 C2 C7 119.0(7) . . ?
C4 C3 C2 120.7(7) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.6(7) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 120.3(7) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 119.4(8) . . ?
C5 C6 H6 120.3 . . ?
C1 C6 H6 120.3 . . ?
O1 C7 N1 122.3(6) . . ?
O1 C7 C2 121.7(6) . . ?
N1 C7 C2 116.0(6) . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C14 120.2(6) . . ?
C10 C9 N1 121.8(6) . . ?
C14 C9 N1 118.0(7) . . ?
C9 C10 C11 120.1(6) . . ?
C9 C10 N2 121.9(6) . . ?
C11 C10 N2 117.9(7) . . ?
C12 C11 C10 119.7(7) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 120.0(6) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C14 C13 C12 119.9(6) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C9 120.1(7) . . ?
C13 C14 H14 120.0 . . ?
C9 C14 H14 120.0 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C16 N2 124.2(6) . . ?
O2 C16 C17 119.7(6) . . ?
N2 C16 C17 116.1(6) . . ?
C18 C17 C22 118.6(7) . . ?
C18 C17 C16 122.1(6) . . ?
C22 C17 C16 119.3(7) . . ?
C17 C18 C19 121.5(8) . . ?
C17 C18 I2 120.1(6) . . ?
C19 C18 I2 118.4(7) . . ?
C18 C19 C20 119.8(9) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C19 C20 C21 119.6(7) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C22 C21 C20 119.6(7) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C21 C22 C17 120.9(7) . . ?
C21 C22 H22 119.5 . . ?
C17 C22 H22 119.5 . . ?
C29 N3 C31 118.8(6) . . ?
C29 N3 C30 123.0(6) . . ?
C31 N3 C30 117.5(6) . . ?
C38 N4 C32 117.6(6) . . ?
C38 N4 C37 124.3(6) . . ?
C32 N4 C37 117.4(5) . . ?
C24 C23 C28 121.2(7) . . ?
C24 C23 I3 121.7(5) . . ?
C28 C23 I3 117.0(6) . . ?
C23 C24 C25 119.4(7) . . ?
C23 C24 C29 122.4(6) . . ?
C25 C24 C29 118.0(7) . . ?
C24 C25 C26 120.3(8) . . ?
C24 C25 H25 119.9 . . ?
C26 C25 H25 119.9 . . ?
C27 C26 C25 119.0(7) . . ?
C27 C26 H26 120.5 . . ?
C25 C26 H26 120.5 . . ?
C28 C27 C26 121.0(7) . . ?
C28 C27 H27 119.5 . . ?
C26 C27 H27 119.5 . . ?
C27 C28 C23 119.1(8) . . ?
C27 C28 H28 120.5 . . ?
C23 C28 H28 120.5 . . ?
O3 C29 N3 122.6(6) . . ?
O3 C29 C24 119.3(6) . . ?
N3 C29 C24 118.1(6) . . ?
N3 C30 H30A 109.5 . . ?
N3 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
N3 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C36 C31 C32 119.9(6) . . ?
C36 C31 N3 119.0(7) . . ?
C32 C31 N3 121.1(6) . . ?
C33 C32 C31 119.3(6) . . ?
C33 C32 N4 118.8(7) . . ?
C31 C32 N4 121.9(6) . . ?
C32 C33 C34 120.5(7) . . ?
C32 C33 H33 119.8 . . ?
C34 C33 H33 119.8 . . ?
C35 C34 C33 119.8(7) . . ?
C35 C34 H34 120.1 . . ?
C33 C34 H34 120.1 . . ?
C34 C35 C36 119.7(7) . . ?
C34 C35 H35 120.2 . . ?
C36 C35 H35 120.2 . . ?
C31 C36 C35 120.7(8) . . ?
C31 C36 H36 119.6 . . ?
C35 C36 H36 119.6 . . ?
N4 C37 H37A 109.5 . . ?
N4 C37 H37B 109.5 . . ?
H37A C37 H37B 109.5 . . ?
N4 C37 H37C 109.5 . . ?
H37A C37 H37C 109.5 . . ?
H37B C37 H37C 109.5 . . ?
O4 C38 N4 123.1(7) . . ?
O4 C38 C39 120.1(6) . . ?
N4 C38 C39 116.6(6) . . ?
C40 C39 C44 118.3(7) . . ?
C40 C39 C38 121.9(7) . . ?
C44 C39 C38 119.5(7) . . ?
C41 C40 C39 120.8(7) . . ?
C41 C40 I4 117.3(6) . . ?
C39 C40 I4 121.9(5) . . ?
C40 C41 C42 120.2(8) . . ?
C40 C41 H41 119.9 . . ?
C42 C41 H41 119.9 . . ?
C43 C42 C41 120.4(7) . . ?
C43 C42 H42 119.8 . . ?
C41 C42 H42 119.8 . . ?
C42 C43 C44 119.5(7) . . ?
C42 C43 H43 120.3 . . ?
C44 C43 H43 120.3 . . ?
C39 C44 C43 120.9(7) . . ?
C39 C44 H44 119.6 . . ?
C43 C44 H44 119.6 . . ?
Cl1 C1S Cl2 111.8(4) . . ?
Cl1 C1S H1S1 109.3 . . ?
Cl2 C1S H1S1 109.3 . . ?
Cl1 C1S H1S2 109.3 . . ?
Cl2 C1S H1S2 109.3 . . ?
H1S1 C1S H1S2 107.9 . . ?
Cl3 C2S Cl4 111.0(4) . . ?
Cl3 C2S H2S1 109.4 . . ?
Cl4 C2S H2S1 109.4 . . ?
Cl3 C2S H2S2 109.4 . . ?
Cl4 C2S H2S2 109.4 . . ?
H2S1 C2S H2S2 108.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.1(11) . . . . ?
I1 C1 C2 C3 -179.7(5) . . . . ?
C6 C1 C2 C7 -177.1(7) . . . . ?
I1 C1 C2 C7 2.0(9) . . . . ?
C1 C2 C3 C4 1.0(11) . . . . ?
C7 C2 C3 C4 179.3(6) . . . . ?
C2 C3 C4 C5 -1.8(11) . . . . ?
C3 C4 C5 C6 0.6(12) . . . . ?
C4 C5 C6 C1 1.4(12) . . . . ?
C2 C1 C6 C5 -2.3(12) . . . . ?
I1 C1 C6 C5 178.5(6) . . . . ?
C9 N1 C7 O1 -4.6(11) . . . . ?
C8 N1 C7 O1 -176.7(7) . . . . ?
C9 N1 C7 C2 174.5(6) . . . . ?
C8 N1 C7 C2 2.4(10) . . . . ?
C1 C2 C7 O1 94.9(9) . . . . ?
C3 C2 C7 O1 -83.4(9) . . . . ?
C1 C2 C7 N1 -84.2(9) . . . . ?
C3 C2 C7 N1 97.5(8) . . . . ?
C7 N1 C9 C10 73.1(9) . . . . ?
C8 N1 C9 C10 -114.2(7) . . . . ?
C7 N1 C9 C14 -108.3(7) . . . . ?
C8 N1 C9 C14 64.4(8) . . . . ?
C14 C9 C10 C11 1.5(10) . . . . ?
N1 C9 C10 C11 -179.9(6) . . . . ?
C14 C9 C10 N2 -179.9(6) . . . . ?
N1 C9 C10 N2 -1.4(10) . . . . ?
C16 N2 C10 C9 72.8(9) . . . . ?
C15 N2 C10 C9 -116.4(7) . . . . ?
C16 N2 C10 C11 -108.6(7) . . . . ?
C15 N2 C10 C11 62.2(9) . . . . ?
C9 C10 C11 C12 -1.2(10) . . . . ?
N2 C10 C11 C12 -179.8(6) . . . . ?
C10 C11 C12 C13 -0.2(10) . . . . ?
C11 C12 C13 C14 1.3(10) . . . . ?
C12 C13 C14 C9 -0.9(10) . . . . ?
C10 C9 C14 C13 -0.5(10) . . . . ?
N1 C9 C14 C13 -179.1(6) . . . . ?
C10 N2 C16 O2 -8.6(11) . . . . ?
C15 N2 C16 O2 -178.6(7) . . . . ?
C10 N2 C16 C17 170.9(6) . . . . ?
C15 N2 C16 C17 0.9(10) . . . . ?
O2 C16 C17 C18 96.6(9) . . . . ?
N2 C16 C17 C18 -82.8(9) . . . . ?
O2 C16 C17 C22 -80.8(9) . . . . ?
N2 C16 C17 C22 99.7(8) . . . . ?
C22 C17 C18 C19 2.0(12) . . . . ?
C16 C17 C18 C19 -175.5(7) . . . . ?
C22 C17 C18 I2 179.5(5) . . . . ?
C16 C17 C18 I2 2.0(10) . . . . ?
C17 C18 C19 C20 -2.3(13) . . . . ?
I2 C18 C19 C20 -179.8(6) . . . . ?
C18 C19 C20 C21 0.9(13) . . . . ?
C19 C20 C21 C22 0.6(12) . . . . ?
C20 C21 C22 C17 -0.8(12) . . . . ?
C18 C17 C22 C21 -0.5(11) . . . . ?
C16 C17 C22 C21 177.1(7) . . . . ?
C28 C23 C24 C25 -0.5(11) . . . . ?
I3 C23 C24 C25 -178.9(5) . . . . ?
C28 C23 C24 C29 -176.2(7) . . . . ?
I3 C23 C24 C29 5.5(10) . . . . ?
C23 C24 C25 C26 0.3(11) . . . . ?
C29 C24 C25 C26 176.1(7) . . . . ?
C24 C25 C26 C27 0.0(11) . . . . ?
C25 C26 C27 C28 -0.1(11) . . . . ?
C26 C27 C28 C23 -0.1(12) . . . . ?
C24 C23 C28 C27 0.5(12) . . . . ?
I3 C23 C28 C27 178.9(6) . . . . ?
C31 N3 C29 O3 -2.0(11) . . . . ?
C30 N3 C29 O3 -172.4(7) . . . . ?
C31 N3 C29 C24 -179.7(6) . . . . ?
C30 N3 C29 C24 9.8(11) . . . . ?
C23 C24 C29 O3 62.8(10) . . . . ?
C25 C24 C29 O3 -112.9(8) . . . . ?
C23 C24 C29 N3 -119.3(8) . . . . ?
C25 C24 C29 N3 65.0(9) . . . . ?
C29 N3 C31 C36 -115.3(8) . . . . ?
C30 N3 C31 C36 55.7(9) . . . . ?
C29 N3 C31 C32 65.9(9) . . . . ?
C30 N3 C31 C32 -123.1(7) . . . . ?
C36 C31 C32 C33 3.9(10) . . . . ?
N3 C31 C32 C33 -177.3(6) . . . . ?
C36 C31 C32 N4 -176.8(6) . . . . ?
N3 C31 C32 N4 2.0(10) . . . . ?
C38 N4 C32 C33 -116.3(7) . . . . ?
C37 N4 C32 C33 54.5(9) . . . . ?
C38 N4 C32 C31 64.4(9) . . . . ?
C37 N4 C32 C31 -124.8(7) . . . . ?
C31 C32 C33 C34 -3.0(10) . . . . ?
N4 C32 C33 C34 177.7(6) . . . . ?
C32 C33 C34 C35 0.3(11) . . . . ?
C33 C34 C35 C36 1.5(11) . . . . ?
C32 C31 C36 C35 -2.1(11) . . . . ?
N3 C31 C36 C35 179.1(6) . . . . ?
C34 C35 C36 C31 -0.6(11) . . . . ?
C32 N4 C38 O4 0.8(11) . . . . ?
C37 N4 C38 O4 -169.3(8) . . . . ?
C32 N4 C38 C39 -175.0(6) . . . . ?
C37 N4 C38 C39 14.9(11) . . . . ?
O4 C38 C39 C40 60.0(10) . . . . ?
N4 C38 C39 C40 -124.1(8) . . . . ?
O4 C38 C39 C44 -113.8(8) . . . . ?
N4 C38 C39 C44 62.1(9) . . . . ?
C44 C39 C40 C41 -1.3(11) . . . . ?
C38 C39 C40 C41 -175.3(7) . . . . ?
C44 C39 C40 I4 -179.6(5) . . . . ?
C38 C39 C40 I4 6.5(10) . . . . ?
C39 C40 C41 C42 2.1(12) . . . . ?
I4 C40 C41 C42 -179.6(6) . . . . ?
C40 C41 C42 C43 -1.2(12) . . . . ?
C41 C42 C43 C44 -0.3(11) . . . . ?
C40 C39 C44 C43 -0.3(10) . . . . ?
C38 C39 C44 C43 173.8(6) . . . . ?
C42 C43 C44 C39 1.1(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        26.35
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         4.927
_refine_diff_density_min         -2.802
_refine_diff_density_rms         0.147