# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

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#
#                 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.
#
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#  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
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
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data_db08

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H8 N2, 2(C9 H4 Cl3 I O)'
_chemical_formula_sum            'C28 H16 Cl6 I2 N2 O2'
_chemical_formula_weight         878.93

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

_cell_length_a                   7.4865(14)
_cell_length_b                   13.522(3)
_cell_length_c                   17.240(3)
_cell_angle_alpha                67.769(9)
_cell_angle_beta                 81.362(9)
_cell_angle_gamma                79.166(9)
_cell_volume                     1580.7(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9944
_cell_measurement_theta_min      2.421
_cell_measurement_theta_max      28.630

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.847
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             844
_exptl_absorpt_coefficient_mu    2.526
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_exptl_absorpt_correction_T_min  0.4510
_exptl_absorpt_correction_T_max  0.9125

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_decay_%        0.00
_diffrn_reflns_number            30410
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.28
_diffrn_reflns_theta_max         32.32
_reflns_number_total             9602
_reflns_number_gt                6763

_reflns_threshold_expression     >2σ(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    
'SHELXS (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)'
_computing_structure_refinement  
'SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)'

_computing_molecular_graphics    
;
ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565)
Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., 
Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). 
J. Appl. Cryst. 39, 453-457
;
_computing_publication_material  SHELXL-97


_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
 The reflection 101, probably affecrted by the beam-stop shadow was omitted
 from the refinement
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0263P)²+0.9272P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         9602
_refine_ls_number_parameters     361
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0303
_refine_ls_wR_factor_ref         0.0733
_refine_ls_wR_factor_gt          0.0633
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_refine_ls_shift/su_max          0.002
_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
I1A I 1.26319(2) 0.517856(15) 0.722374(11) 0.05169(6) Uani 1 1 d . . .
Cl1A Cl 1.70181(11) 0.97588(6) 0.73615(5) 0.0699(2) Uani 1 1 d . . .
Cl2A Cl 1.37297(14) 0.86567(8) 1.04985(6) 0.0845(3) Uani 1 1 d . . .
Cl3A Cl 1.44470(11) 0.62079(7) 1.06603(5) 0.06713(19) Uani 1 1 d . . .
O1A O 1.7375(3) 0.75083(16) 0.76364(12) 0.0566(5) Uani 1 1 d . . .
C1A C 1.4753(3) 0.5757(2) 0.74179(17) 0.0488(6) Uani 1 1 d . . .
C2A C 1.6017(3) 0.6078(2) 0.75362(16) 0.0484(6) Uani 1 1 d . . .
C3A C 1.7669(3) 0.6424(2) 0.76541(19) 0.0535(6) Uani 1 1 d . . .
H3A H 1.8110 0.5942 0.8190 0.064 Uiso 1 1 calc R . .
H3B H 1.8610 0.6364 0.7215 0.064 Uiso 1 1 calc R . .
C4A C 1.6533(3) 0.7704(2) 0.83274(16) 0.0445(5) Uani 1 1 d . . .
C5A C 1.6256(3) 0.8776(2) 0.82764(18) 0.0499(6) Uani 1 1 d . . .
C6A C 1.5407(4) 0.9057(2) 0.89359(19) 0.0566(7) Uani 1 1 d . . .
H6A H 1.5221 0.9776 0.8888 0.068 Uiso 1 1 calc R . .
C7A C 1.4821(4) 0.8277(2) 0.96766(18) 0.0533(6) Uani 1 1 d . . .
C8A C 1.5100(3) 0.7211(2) 0.97397(16) 0.0481(6) Uani 1 1 d . . .
C9A C 1.5929(3) 0.6926(2) 0.90656(17) 0.0471(6) Uani 1 1 d . . .
H9A H 1.6081 0.6209 0.9108 0.056 Uiso 1 1 calc R . .
I1B I 0.08025(3) 0.175522(16) 0.467355(13) 0.06277(7) Uani 1 1 d . . .
Cl1B Cl -0.07239(14) -0.07937(6) 0.16079(6) 0.0808(3) Uani 1 1 d . . .
Cl2B Cl 0.07940(10) 0.30637(7) -0.05705(4) 0.06517(19) Uani 1 1 d . . .
Cl3B Cl -0.11741(12) 0.41185(6) 0.07516(5) 0.06664(19) Uani 1 1 d . . .
O1B O -0.2251(3) 0.03345(14) 0.27277(11) 0.0510(4) Uani 1 1 d . . .
C1B C -0.0943(4) 0.1390(2) 0.40692(18) 0.0585(7) Uani 1 1 d . . .
C2B C -0.1935(4) 0.1138(2) 0.37268(17) 0.0519(6) Uani 1 1 d . . .
C3B C -0.3175(4) 0.0778(2) 0.33442(16) 0.0506(6) Uani 1 1 d . . .
H3C H -0.3814 0.0235 0.3782 0.061 Uiso 1 1 calc R . .
H3D H -0.4079 0.1385 0.3078 0.061 Uiso 1 1 calc R . .
C4B C -0.1586(3) 0.1021(2) 0.19797(15) 0.0423(5) Uani 1 1 d . . .
C5B C -0.0768(4) 0.0574(2) 0.13794(17) 0.0484(6) Uani 1 1 d . . .
C6B C -0.0030(3) 0.1195(2) 0.06098(17) 0.0514(6) Uani 1 1 d . . .
H6B H 0.0537 0.0877 0.0226 0.062 Uiso 1 1 calc R . .
C7B C -0.0129(3) 0.2290(2) 0.04062(15) 0.0464(6) Uani 1 1 d . . .
C8B C -0.0964(3) 0.2748(2) 0.09854(16) 0.0444(5) Uani 1 1 d . . .
C9B C -0.1667(3) 0.2122(2) 0.17721(15) 0.0428(5) Uani 1 1 d . . .
H9B H -0.2193 0.2440 0.2161 0.051 Uiso 1 1 calc R . .
N1 N 0.9580(3) 0.4416(2) 0.68899(18) 0.0637(6) Uani 1 1 d . . .
N2 N 0.3291(4) 0.2312(2) 0.54567(17) 0.0671(7) Uani 1 1 d . . .
C10 C 0.7787(4) 0.4502(3) 0.58227(19) 0.0606(7) Uani 1 1 d . . .
H10 H 0.7449 0.4861 0.5277 0.073 Uiso 1 1 calc R . .
C11 C 0.9016(4) 0.4882(3) 0.6120(2) 0.0679(8) Uani 1 1 d . . .
H11 H 0.9482 0.5504 0.5760 0.082 Uiso 1 1 calc R . .
C12 C 0.8823(5) 0.3555(3) 0.7391(2) 0.0725(9) Uani 1 1 d . . .
H12 H 0.9156 0.3226 0.7940 0.087 Uiso 1 1 calc R . .
C13 C 0.7579(5) 0.3118(2) 0.71532(19) 0.0648(8) Uani 1 1 d . . .
H13 H 0.7092 0.2515 0.7535 0.078 Uiso 1 1 calc R . .
C14 C 0.7059(3) 0.3581(2) 0.63426(16) 0.0470(6) Uani 1 1 d . . .
C15 C 0.5749(3) 0.3132(2) 0.60448(16) 0.0453(5) Uani 1 1 d . . .
C16 C 0.4324(4) 0.2647(2) 0.65657(18) 0.0611(7) Uani 1 1 d . . .
H16 H 0.4167 0.2581 0.7128 0.073 Uiso 1 1 calc R . .
C17 C 0.3134(5) 0.2262(3) 0.6249(2) 0.0697(9) Uani 1 1 d . . .
H17 H 0.2169 0.1951 0.6608 0.084 Uiso 1 1 calc R . .
C18 C 0.4672(5) 0.2764(3) 0.4964(2) 0.0761(10) Uani 1 1 d . . .
H18 H 0.4812 0.2805 0.4408 0.091 Uiso 1 1 calc R . .
C19 C 0.5911(4) 0.3179(3) 0.52209(19) 0.0665(8) Uani 1 1 d . . .
H19 H 0.6856 0.3490 0.4845 0.080 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1A C1A 2.017(3) . ?
Cl1A C5A 1.734(3) . ?
Cl2A C7A 1.728(3) . ?
Cl3A C8A 1.728(3) . ?
O1A C4A 1.356(3) . ?
O1A C3A 1.430(3) . ?
C1A C2A 1.186(4) . ?
C2A C3A 1.468(4) . ?
C3A H3A 0.9700 . ?
C3A H3B 0.9700 . ?
C4A C9A 1.387(4) . ?
C4A C5A 1.395(4) . ?
C5A C6A 1.364(4) . ?
C6A C7A 1.387(4) . ?
C6A H6A 0.9300 . ?
C7A C8A 1.381(4) . ?
C8A C9A 1.384(4) . ?
C9A H9A 0.9300 . ?
I1B C1B 2.019(3) . ?
Cl1B C5B 1.734(3) . ?
Cl2B C7B 1.731(3) . ?
Cl3B C8B 1.722(3) . ?
O1B C4B 1.360(3) . ?
O1B C3B 1.440(3) . ?
C1B C2B 1.182(4) . ?
C2B C3B 1.459(4) . ?
C3B H3C 0.9700 . ?
C3B H3D 0.9700 . ?
C4B C9B 1.384(3) . ?
C4B C5B 1.399(3) . ?
C5B C6B 1.372(4) . ?
C6B C7B 1.376(4) . ?
C6B H6B 0.9300 . ?
C7B C8B 1.380(4) . ?
C8B C9B 1.385(3) . ?
C9B H9B 0.9300 . ?
N1 C12 1.327(4) . ?
N1 C11 1.332(4) . ?
N2 C18 1.322(4) . ?
N2 C17 1.330(4) . ?
C10 C11 1.375(4) . ?
C10 C14 1.384(4) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C12 C13 1.375(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.381(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.485(3) . ?
C15 C16 1.380(4) . ?
C15 C19 1.385(4) . ?
C16 C17 1.378(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.370(4) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?

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
C4A O1A C3A 118.6(2) . . ?
C2A C1A I1A 178.8(2) . . ?
C1A C2A C3A 175.8(3) . . ?
O1A C3A C2A 113.1(2) . . ?
O1A C3A H3A 109.0 . . ?
C2A C3A H3A 109.0 . . ?
O1A C3A H3B 109.0 . . ?
C2A C3A H3B 109.0 . . ?
H3A C3A H3B 107.8 . . ?
O1A C4A C9A 124.9(2) . . ?
O1A C4A C5A 116.5(2) . . ?
C9A C4A C5A 118.6(2) . . ?
C6A C5A C4A 120.9(3) . . ?
C6A C5A Cl1A 119.8(2) . . ?
C4A C5A Cl1A 119.3(2) . . ?
C5A C6A C7A 120.4(3) . . ?
C5A C6A H6A 119.8 . . ?
C7A C6A H6A 119.8 . . ?
C8A C7A C6A 119.3(3) . . ?
C8A C7A Cl2A 121.2(2) . . ?
C6A C7A Cl2A 119.5(2) . . ?
C7A C8A C9A 120.4(3) . . ?
C7A C8A Cl3A 120.9(2) . . ?
C9A C8A Cl3A 118.7(2) . . ?
C8A C9A C4A 120.3(2) . . ?
C8A C9A H9A 119.8 . . ?
C4A C9A H9A 119.8 . . ?
C4B O1B C3B 118.30(19) . . ?
C2B C1B I1B 177.6(3) . . ?
C1B C2B C3B 177.0(3) . . ?
O1B C3B C2B 112.9(2) . . ?
O1B C3B H3C 109.0 . . ?
C2B C3B H3C 109.0 . . ?
O1B C3B H3D 109.0 . . ?
C2B C3B H3D 109.0 . . ?
H3C C3B H3D 107.8 . . ?
O1B C4B C9B 124.9(2) . . ?
O1B C4B C5B 117.0(2) . . ?
C9B C4B C5B 118.1(2) . . ?
C6B C5B C4B 121.5(2) . . ?
C6B C5B Cl1B 119.3(2) . . ?
C4B C5B Cl1B 119.1(2) . . ?
C5B C6B C7B 119.9(2) . . ?
C5B C6B H6B 120.0 . . ?
C7B C6B H6B 120.0 . . ?
C6B C7B C8B 119.3(2) . . ?
C6B C7B Cl2B 119.3(2) . . ?
C8B C7B Cl2B 121.4(2) . . ?
C7B C8B C9B 121.2(2) . . ?
C7B C8B Cl3B 121.1(2) . . ?
C9B C8B Cl3B 117.8(2) . . ?
C4B C9B C8B 119.9(2) . . ?
C4B C9B H9B 120.0 . . ?
C8B C9B H9B 120.0 . . ?
C12 N1 C11 115.7(2) . . ?
C18 N2 C17 116.5(3) . . ?
C11 C10 C14 119.5(3) . . ?
C11 C10 H10 120.3 . . ?
C14 C10 H10 120.3 . . ?
N1 C11 C10 124.2(3) . . ?
N1 C11 H11 117.9 . . ?
C10 C11 H11 117.9 . . ?
N1 C12 C13 124.3(3) . . ?
N1 C12 H12 117.8 . . ?
C13 C12 H12 117.8 . . ?
C12 C13 C14 119.5(3) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C13 C14 C10 116.7(2) . . ?
C13 C14 C15 121.9(2) . . ?
C10 C14 C15 121.3(2) . . ?
C16 C15 C19 116.6(2) . . ?
C16 C15 C14 122.4(2) . . ?
C19 C15 C14 121.0(2) . . ?
C17 C16 C15 119.7(3) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
N2 C17 C16 123.5(3) . . ?
N2 C17 H17 118.2 . . ?
C16 C17 H17 118.2 . . ?
N2 C18 C19 124.1(3) . . ?
N2 C18 H18 118.0 . . ?
C19 C18 H18 118.0 . . ?
C18 C19 C15 119.6(3) . . ?
C18 C19 H19 120.2 . . ?
C15 C19 H19 120.2 . . ?

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
I1A C1A C2A C3A 41(14) . . . . ?
C4A O1A C3A C2A 77.5(3) . . . . ?
C1A C2A C3A O1A 150(4) . . . . ?
C3A O1A C4A C9A 0.3(3) . . . . ?
C3A O1A C4A C5A -179.2(2) . . . . ?
O1A C4A C5A C6A 179.5(2) . . . . ?
C9A C4A C5A C6A -0.2(4) . . . . ?
O1A C4A C5A Cl1A -0.9(3) . . . . ?
C9A C4A C5A Cl1A 179.49(18) . . . . ?
C4A C5A C6A C7A 0.8(4) . . . . ?
Cl1A C5A C6A C7A -178.8(2) . . . . ?
C5A C6A C7A C8A -0.2(4) . . . . ?
C5A C6A C7A Cl2A -179.4(2) . . . . ?
C6A C7A C8A C9A -1.1(4) . . . . ?
Cl2A C7A C8A C9A 178.07(19) . . . . ?
C6A C7A C8A Cl3A 178.3(2) . . . . ?
Cl2A C7A C8A Cl3A -2.6(3) . . . . ?
C7A C8A C9A C4A 1.8(4) . . . . ?
Cl3A C8A C9A C4A -177.59(18) . . . . ?
O1A C4A C9A C8A 179.3(2) . . . . ?
C5A C4A C9A C8A -1.1(3) . . . . ?
I1B C1B C2B C3B 44(11) . . . . ?
C4B O1B C3B C2B -71.9(3) . . . . ?
C1B C2B C3B O1B -107(6) . . . . ?
C3B O1B C4B C9B 2.5(3) . . . . ?
C3B O1B C4B C5B -177.2(2) . . . . ?
O1B C4B C5B C6B -179.0(2) . . . . ?
C9B C4B C5B C6B 1.3(4) . . . . ?
O1B C4B C5B Cl1B 2.1(3) . . . . ?
C9B C4B C5B Cl1B -177.60(18) . . . . ?
C4B C5B C6B C7B -1.8(4) . . . . ?
Cl1B C5B C6B C7B 177.10(19) . . . . ?
C5B C6B C7B C8B 0.4(4) . . . . ?
C5B C6B C7B Cl2B -179.49(19) . . . . ?
C6B C7B C8B C9B 1.4(3) . . . . ?
Cl2B C7B C8B C9B -178.69(18) . . . . ?
C6B C7B C8B Cl3B -178.35(19) . . . . ?
Cl2B C7B C8B Cl3B 1.6(3) . . . . ?
O1B C4B C9B C8B -179.2(2) . . . . ?
C5B C4B C9B C8B 0.5(3) . . . . ?
C7B C8B C9B C4B -1.9(3) . . . . ?
Cl3B C8B C9B C4B 177.87(18) . . . . ?
C12 N1 C11 C10 -2.6(5) . . . . ?
C14 C10 C11 N1 0.3(5) . . . . ?
C11 N1 C12 C13 2.3(5) . . . . ?
N1 C12 C13 C14 0.3(6) . . . . ?
C12 C13 C14 C10 -2.6(5) . . . . ?
C12 C13 C14 C15 178.8(3) . . . . ?
C11 C10 C14 C13 2.3(4) . . . . ?
C11 C10 C14 C15 -179.1(3) . . . . ?
C13 C14 C15 C16 33.8(4) . . . . ?
C10 C14 C15 C16 -144.8(3) . . . . ?
C13 C14 C15 C19 -146.0(3) . . . . ?
C10 C14 C15 C19 35.4(4) . . . . ?
C19 C15 C16 C17 -1.3(5) . . . . ?
C14 C15 C16 C17 178.9(3) . . . . ?
C18 N2 C17 C16 -0.3(5) . . . . ?
C15 C16 C17 N2 1.2(5) . . . . ?
C17 N2 C18 C19 -0.3(6) . . . . ?
N2 C18 C19 C15 0.1(6) . . . . ?
C16 C15 C19 C18 0.7(5) . . . . ?
C14 C15 C19 C18 -179.5(3) . . . . ?

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
C3A H3B I1A 0.97 3.13 3.867(3) 133.7 1_655
C3A H3B I1B 0.97 3.31 3.959(3) 125.7 2_766
C6A H6A Cl2A 0.93 2.97 3.762(3) 144.5 2_877
C12 H12 Cl2B 0.93 2.93 3.793(3) 155.6 1_656

_diffrn_measured_fraction_theta_max 0.851
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.713
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.067
_database_code_depnum_ccdc_archive 'CCDC 986300'
#######################################################################
#
#                 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_mk234

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H36 N 1+, 2(C9 H4 Cl3 I O) Cl 1-'
_chemical_formula_sum            'C34 H44 Cl7 I2 N O2'
_chemical_formula_weight         1000.65

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'
Cl Cl 0.1484 0.1585 '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
_symmetry_space_group_name_Hall  '-P 2n 2ab'

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

_cell_length_a                   8.557(2)
_cell_length_b                   14.816(3)
_cell_length_c                   31.189(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3954.2(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    9694
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      37.28
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.681
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1984
_exptl_absorpt_coefficient_mu    2.095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_exptl_absorpt_correction_T_min  0.5999
_exptl_absorpt_correction_T_max  0.7458

_exptl_special_details           
; 
Bruker KRYOFLEX low temperature device.
Crystallization gave a unique millimetric crystal that was cut to
reasonable dimensions for data collection. 
 ? 
;

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_decay_%        0.00
_diffrn_reflns_number            91960
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_sigmaI/netI    0.0214
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_limit_l_max       51
_diffrn_reflns_theta_min         2.72
_diffrn_reflns_theta_max         38.01
_reflns_number_total             10012
_reflns_number_gt                8043
_reflns_threshold_expression     'I > 2σ(I)'

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    
'SHELXS (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)'
_computing_structure_refinement  
'SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)'

_computing_molecular_graphics    
;
ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565)
Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., 
Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). 
J. Appl. Cryst. 39, 453-457
;
_computing_publication_material  SHELXL-97

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0120P)²+4.1489P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         10012
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0267
_refine_ls_wR_factor_ref         0.0537
_refine_ls_wR_factor_gt          0.0497
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.002
_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 0.492796(9) 0.515159(6) 0.168260(3) 0.01442(2) Uani 1 1 d . . .
Cl1 Cl 0.12033(4) 0.88827(2) 0.063315(11) 0.01974(6) Uani 1 1 d . . .
Cl2 Cl 0.32366(5) 1.05596(3) -0.078773(12) 0.02485(7) Uani 1 1 d . . .
Cl3 Cl 0.60735(4) 0.91636(3) -0.084038(11) 0.02285(7) Uani 1 1 d . . .
C1 C 0.49810(17) 0.59599(9) 0.11586(5) 0.0176(2) Uani 1 1 d . . .
C2 C 0.50010(17) 0.64640(9) 0.08579(5) 0.0183(2) Uani 1 1 d . . .
C3 C 0.50837(18) 0.70636(10) 0.04861(5) 0.0191(2) Uani 1 1 d . . .
H3A H 0.6098 0.7385 0.0483 0.023 Uiso 1 1 calc R . .
H3B H 0.4997 0.6708 0.0219 0.023 Uiso 1 1 calc R . .
O1 O 0.38237(13) 0.77023(7) 0.05118(3) 0.01816(19) Uani 1 1 d . . .
C4 C 0.37727(16) 0.83369(9) 0.01986(4) 0.0144(2) Uani 1 1 d . . .
C5 C 0.25524(16) 0.89670(9) 0.02231(4) 0.0144(2) Uani 1 1 d . . .
C6 C 0.24009(17) 0.96439(9) -0.00793(5) 0.0166(2) Uani 1 1 d . . .
H6 H 0.1568 1.0065 -0.0058 0.020 Uiso 1 1 calc R . .
C7 C 0.34671(17) 0.97087(9) -0.04145(4) 0.0167(2) Uani 1 1 d . . .
C8 C 0.46809(16) 0.90930(9) -0.04419(4) 0.0161(2) Uani 1 1 d . . .
C9 C 0.48316(16) 0.84047(9) -0.01386(4) 0.0164(2) Uani 1 1 d . . .
H9 H 0.5660 0.7981 -0.0163 0.020 Uiso 1 1 calc R . .
C10 C 0.37309(15) 0.08030(9) 0.26935(4) 0.0139(2) Uani 1 1 d . . .
H10A H 0.3417 0.1257 0.2477 0.017 Uiso 1 1 calc R . .
H10B H 0.2807 0.0422 0.2754 0.017 Uiso 1 1 calc R . .
Cl4 Cl 0.5000 0.40313(3) 0.2500 0.01679(8) Uani 1 2 d S . .
N1 N 0.5000 0.02097(10) 0.2500 0.0109(2) Uani 1 2 d S . .
C11 C 0.41786(16) 0.12956(9) 0.31035(5) 0.0171(2) Uani 1 1 d . . .
H11A H 0.5289 0.1481 0.3087 0.021 Uiso 1 1 calc R . .
H11B H 0.4062 0.0881 0.3351 0.021 Uiso 1 1 calc R . .
C12 C 0.31589(17) 0.21283(9) 0.31737(5) 0.0185(2) Uani 1 1 d . . .
H12A H 0.3336 0.2563 0.2937 0.022 Uiso 1 1 calc R . .
H12B H 0.2045 0.1949 0.3168 0.022 Uiso 1 1 calc R . .
C13 C 0.35210(19) 0.25835(11) 0.36002(5) 0.0238(3) Uani 1 1 d . . .
H13A H 0.4636 0.2732 0.3613 0.036 Uiso 1 1 calc R . .
H13B H 0.3256 0.2174 0.3836 0.036 Uiso 1 1 calc R . .
H13C H 0.2904 0.3138 0.3626 0.036 Uiso 1 1 calc R . .
C14 C 0.42166(15) -0.03725(9) 0.21616(4) 0.0130(2) Uani 1 1 d . . .
H14A H 0.3746 0.0030 0.1944 0.016 Uiso 1 1 calc R . .
H14B H 0.3354 -0.0711 0.2299 0.016 Uiso 1 1 calc R . .
C15 C 0.52733(16) -0.10440(9) 0.19339(4) 0.0160(2) Uani 1 1 d . . .
H15A H 0.5728 -0.1467 0.2146 0.019 Uiso 1 1 calc R . .
H15B H 0.6142 -0.0718 0.1792 0.019 Uiso 1 1 calc R . .
C16 C 0.43412(17) -0.15739(10) 0.15986(5) 0.0189(2) Uani 1 1 d . . .
H16A H 0.3792 -0.1141 0.1410 0.023 Uiso 1 1 calc R . .
H16B H 0.5080 -0.1921 0.1418 0.023 Uiso 1 1 calc R . .
C17 C 0.3146(2) -0.22232(11) 0.17878(6) 0.0284(3) Uani 1 1 d . . .
H17A H 0.2340 -0.1880 0.1940 0.043 Uiso 1 1 calc R . .
H17B H 0.3668 -0.2634 0.1988 0.043 Uiso 1 1 calc R . .
H17C H 0.2661 -0.2573 0.1557 0.043 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.0267(14) . ?
Cl1 C5 1.7273(14) . ?
Cl2 C7 1.7271(14) . ?
Cl3 C8 1.7250(14) . ?
C1 C2 1.1990(19) . ?
C2 C3 1.462(2) . ?
C3 O1 1.4368(17) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
O1 C4 1.3565(16) . ?
C4 C9 1.3918(19) . ?
C4 C5 1.4027(19) . ?
C5 C6 1.3828(19) . ?
C6 C7 1.391(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.385(2) . ?
C8 C9 1.3971(19) . ?
C9 H9 0.9500 . ?
C10 C11 1.5213(19) . ?
C10 N1 1.5220(15) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
N1 C14 1.5189(15) 3_655 ?
N1 C14 1.5190(15) . ?
N1 C10 1.5221(15) 3_655 ?
C11 C12 1.5270(19) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.523(2) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.5205(18) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.5317(19) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 C17 1.523(2) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 I1 177.64(13) . . ?
C1 C2 C3 177.76(16) . . ?
O1 C3 C2 108.64(12) . . ?
O1 C3 H3A 110.0 . . ?
C2 C3 H3A 110.0 . . ?
O1 C3 H3B 110.0 . . ?
C2 C3 H3B 110.0 . . ?
H3A C3 H3B 108.3 . . ?
C4 O1 C3 116.14(11) . . ?
O1 C4 C9 124.96(12) . . ?
O1 C4 C5 116.49(12) . . ?
C9 C4 C5 118.55(12) . . ?
C6 C5 C4 121.01(12) . . ?
C6 C5 Cl1 119.65(11) . . ?
C4 C5 Cl1 119.32(10) . . ?
C5 C6 C7 120.09(13) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 119.52(12) . . ?
C8 C7 Cl2 121.66(11) . . ?
C6 C7 Cl2 118.82(11) . . ?
C7 C8 C9 120.55(12) . . ?
C7 C8 Cl3 121.50(11) . . ?
C9 C8 Cl3 117.93(11) . . ?
C4 C9 C8 120.28(13) . . ?
C4 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C11 C10 N1 115.52(10) . . ?
C11 C10 H10A 108.4 . . ?
N1 C10 H10A 108.4 . . ?
C11 C10 H10B 108.4 . . ?
N1 C10 H10B 108.4 . . ?
H10A C10 H10B 107.5 . . ?
C14 N1 C14 110.79(13) 3_655 . ?
C14 N1 C10 111.55(7) 3_655 . ?
C14 N1 C10 106.78(7) . . ?
C14 N1 C10 106.78(7) 3_655 3_655 ?
C14 N1 C10 111.55(7) . 3_655 ?
C10 N1 C10 109.43(13) . 3_655 ?
C10 C11 C12 111.36(11) . . ?
C10 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C13 C12 C11 111.51(12) . . ?
C13 C12 H12A 109.3 . . ?
C11 C12 H12A 109.3 . . ?
C13 C12 H12B 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 C15 115.70(10) . . ?
N1 C14 H14A 108.4 . . ?
C15 C14 H14A 108.4 . . ?
N1 C14 H14B 108.4 . . ?
C15 C14 H14B 108.4 . . ?
H14A C14 H14B 107.4 . . ?
C14 C15 C16 110.16(11) . . ?
C14 C15 H15A 109.6 . . ?
C16 C15 H15A 109.6 . . ?
C14 C15 H15B 109.6 . . ?
C16 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
C17 C16 C15 114.14(13) . . ?
C17 C16 H16A 108.7 . . ?
C15 C16 H16A 108.7 . . ?
C17 C16 H16B 108.7 . . ?
C15 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C1 C2 C3 130(4) . . . . ?
C1 C2 C3 O1 -173(66) . . . . ?
C2 C3 O1 C4 177.21(12) . . . . ?
C3 O1 C4 C9 0.3(2) . . . . ?
C3 O1 C4 C5 -179.56(12) . . . . ?
O1 C4 C5 C6 179.68(12) . . . . ?
C9 C4 C5 C6 -0.2(2) . . . . ?
O1 C4 C5 Cl1 -1.34(17) . . . . ?
C9 C4 C5 Cl1 178.78(10) . . . . ?
C4 C5 C6 C7 0.0(2) . . . . ?
Cl1 C5 C6 C7 -178.98(11) . . . . ?
C5 C6 C7 C8 -0.2(2) . . . . ?
C5 C6 C7 Cl2 179.71(11) . . . . ?
C6 C7 C8 C9 0.6(2) . . . . ?
Cl2 C7 C8 C9 -179.28(11) . . . . ?
C6 C7 C8 Cl3 -177.83(11) . . . . ?
Cl2 C7 C8 Cl3 2.25(17) . . . . ?
O1 C4 C9 C8 -179.25(13) . . . . ?
C5 C4 C9 C8 0.6(2) . . . . ?
C7 C8 C9 C4 -0.9(2) . . . . ?
Cl3 C8 C9 C4 177.67(11) . . . . ?
C11 C10 N1 C14 46.20(15) . . . 3_655 ?
C11 C10 N1 C14 167.39(11) . . . . ?
C11 C10 N1 C10 -71.74(10) . . . 3_655 ?
N1 C10 C11 C12 157.13(11) . . . . ?
C10 C11 C12 C13 175.74(12) . . . . ?
C14 N1 C14 C15 -56.62(9) 3_655 . . . ?
C10 N1 C14 C15 -178.28(11) . . . . ?
C10 N1 C14 C15 62.20(14) 3_655 . . . ?
N1 C14 C15 C16 -179.21(11) . . . . ?
C14 C15 C16 C17 -68.92(16) . . . . ?

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
C3 H3B Cl1 0.99 2.98 3.8820(16) 151.8 4_565
C10 H10B I1 0.99 3.05 3.9125(15) 146.0 6_556
C14 H14A I1 0.99 3.25 3.9259(15) 126.8 8_655
C14 H14B Cl4 0.99 2.96 3.8617(15) 151.5 6_556

_diffrn_measured_fraction_theta_max 0.929
_diffrn_reflns_theta_full        33.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.237
_refine_diff_density_min         -1.766
_refine_diff_density_rms         0.100
_database_code_depnum_ccdc_archive 'CCDC 986301'
#######################################################################
#
#                 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_mk220

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C9 H4 Cl3 I O),C16 H36 N 1+,  I 1-'
_chemical_formula_sum            'C34 H44 Cl6 I3 N O2'
_chemical_formula_weight         1092.10

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'
Cl Cl 0.1484 0.1585 '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   'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'

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

_cell_length_a                   8.9174(9)
_cell_length_b                   15.2187(12)
_cell_length_c                   31.429(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4265.3(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9907
_cell_measurement_theta_min      2.28
_cell_measurement_theta_max      28.59
_exptl_crystal_description       table
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2128
_exptl_absorpt_coefficient_mu    2.603
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_exptl_absorpt_correction_T_min  0.3943
_exptl_absorpt_correction_T_max  0.5199

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_decay_%        0.00
_diffrn_reflns_number            61875
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0151
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       43
_diffrn_reflns_theta_min         2.59
_diffrn_reflns_theta_max         29.25
_reflns_number_total             5811
_reflns_number_gt                4382
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    
'SHELXS (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)'
_computing_structure_refinement  
'SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)'

_computing_molecular_graphics    
;
ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565)
Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., 
Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). 
J. Appl. Cryst. 39, 453-457
;
_computing_publication_material  SHELXL-97


_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0250P)²+7.4055P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5811
_refine_ls_number_parameters     211
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0524
_refine_ls_R_factor_gt           0.0341
_refine_ls_wR_factor_ref         0.0869
_refine_ls_wR_factor_gt          0.0736
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_restrained_S_all      1.079
_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 0.48282(3) 0.525804(15) 0.340423(8) 0.05522(8) Uani 1 1 d . . .
I2 I 0.5000 0.40386(2) 0.2500 0.05304(9) Uani 1 2 d S . .
Cl1 Cl 0.58050(17) 0.93167(10) 0.58547(4) 0.0905(4) Uani 1 1 d . . .
Cl2 Cl 0.30821(18) 1.06485(10) 0.57456(5) 0.1072(5) Uani 1 1 d . . .
Cl3 Cl 0.12687(13) 0.88520(8) 0.43757(4) 0.0759(3) Uani 1 1 d . . .
C1 C 0.4851(5) 0.6040(3) 0.39253(14) 0.0629(10) Uani 1 1 d . . .
C2 C 0.4877(5) 0.6526(3) 0.42180(14) 0.0631(10) Uani 1 1 d . . .
C3 C 0.4952(5) 0.7131(3) 0.45803(15) 0.0755(13) Uani 1 1 d . . .
H3A H 0.4894 0.6805 0.4845 0.091 Uiso 1 1 calc R . .
H3B H 0.5892 0.7451 0.4576 0.091 Uiso 1 1 calc R . .
C4 C 0.3665(4) 0.8386(2) 0.48398(11) 0.0532(8) Uani 1 1 d . . .
C5 C 0.4656(5) 0.8493(3) 0.51757(12) 0.0590(9) Uani 1 1 d . . .
H5 H 0.5432 0.8093 0.5215 0.071 Uiso 1 1 calc R . .
C6 C 0.4498(5) 0.9193(3) 0.54532(11) 0.0586(9) Uani 1 1 d . . .
C7 C 0.3345(5) 0.9771(3) 0.54021(13) 0.0653(11) Uani 1 1 d . . .
C8 C 0.2354(5) 0.9670(3) 0.50690(13) 0.0647(10) Uani 1 1 d . . .
H8 H 0.1574 1.0069 0.5033 0.078 Uiso 1 1 calc R . .
C9 C 0.2515(4) 0.8982(2) 0.47895(11) 0.0535(8) Uani 1 1 d . . .
O1 O 0.3730(3) 0.77243(18) 0.45496(9) 0.0708(8) Uani 1 1 d . . .
N1 N 1.0000 0.5265(2) 0.2500 0.0372(7) Uani 1 2 d S . .
C10 C 0.9228(4) 0.4699(2) 0.21685(10) 0.0433(7) Uani 1 1 d . . .
H10A H 0.8736 0.5084 0.1966 0.052 Uiso 1 1 calc R . .
H10B H 0.8453 0.4358 0.2309 0.052 Uiso 1 1 calc R . .
C11 C 1.0239(4) 0.4072(3) 0.19246(13) 0.0611(10) Uani 1 1 d . . .
H11A H 1.0772 0.3700 0.2124 0.073 Uiso 1 1 calc R . .
H11B H 1.0974 0.4407 0.1765 0.073 Uiso 1 1 calc R . .
C12 C 0.9331(5) 0.3502(3) 0.16200(14) 0.0726(12) Uani 1 1 d . . .
H12A H 0.8682 0.3880 0.1453 0.087 Uiso 1 1 calc R . .
H12B H 1.0017 0.3215 0.1425 0.087 Uiso 1 1 calc R . .
C13 C 0.8395(6) 0.2819(3) 0.1827(2) 0.111(2) Uani 1 1 d . . .
H13A H 0.9021 0.2442 0.1996 0.166 Uiso 1 1 calc R . .
H13B H 0.7895 0.2477 0.1614 0.166 Uiso 1 1 calc R . .
H13C H 0.7662 0.3095 0.2007 0.166 Uiso 1 1 calc R . .
C14 C 0.8795(3) 0.5837(2) 0.27041(10) 0.0429(7) Uani 1 1 d . . .
H14A H 0.8318 0.6182 0.2483 0.052 Uiso 1 1 calc R . .
H14B H 0.8035 0.5456 0.2826 0.052 Uiso 1 1 calc R . .
C15 C 0.9344(4) 0.6454(2) 0.30474(12) 0.0568(9) Uani 1 1 d . . .
H15A H 0.9765 0.6114 0.3279 0.068 Uiso 1 1 calc R . .
H15B H 1.0133 0.6823 0.2933 0.068 Uiso 1 1 calc R . .
C16 C 0.8113(5) 0.7022(3) 0.32150(17) 0.0803(14) Uani 1 1 d . . .
H16A H 0.7294 0.6650 0.3309 0.096 Uiso 1 1 calc R . .
H16B H 0.7740 0.7389 0.2986 0.096 Uiso 1 1 calc R . .
C17 C 0.8591(6) 0.7605(3) 0.35800(15) 0.0865(15) Uani 1 1 d . . .
H17A H 0.8984 0.7249 0.3806 0.130 Uiso 1 1 calc R . .
H17B H 0.7742 0.7931 0.3682 0.130 Uiso 1 1 calc R . .
H17C H 0.9351 0.8006 0.3484 0.130 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.025(4) . ?
Cl1 C6 1.728(4) . ?
Cl2 C7 1.733(4) . ?
Cl3 C9 1.722(4) . ?
C1 C2 1.180(5) . ?
C2 C3 1.466(6) . ?
C3 O1 1.418(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 O1 1.359(4) . ?
C4 C9 1.378(5) . ?
C4 C5 1.387(5) . ?
C5 C6 1.384(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.362(6) . ?
C7 C8 1.378(6) . ?
C8 C9 1.375(5) . ?
C8 H8 0.9300 . ?
N1 C10 1.517(4) 3_755 ?
N1 C10 1.517(4) . ?
N1 C14 1.524(3) . ?
N1 C14 1.524(3) 3_755 ?
C10 C11 1.520(5) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.525(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.484(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 C15 1.512(5) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.493(5) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.512(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 I1 177.2(4) . . ?
C1 C2 C3 178.5(5) . . ?
O1 C3 C2 108.2(3) . . ?
O1 C3 H3A 110.1 . . ?
C2 C3 H3A 110.1 . . ?
O1 C3 H3B 110.1 . . ?
C2 C3 H3B 110.1 . . ?
H3A C3 H3B 108.4 . . ?
O1 C4 C9 116.3(3) . . ?
O1 C4 C5 124.8(3) . . ?
C9 C4 C5 118.9(3) . . ?
C6 C5 C4 120.4(4) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C7 C6 C5 119.9(4) . . ?
C7 C6 Cl1 121.7(3) . . ?
C5 C6 Cl1 118.4(3) . . ?
C6 C7 C8 120.1(4) . . ?
C6 C7 Cl2 121.7(3) . . ?
C8 C7 Cl2 118.2(4) . . ?
C9 C8 C7 120.2(4) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C4 120.4(4) . . ?
C8 C9 Cl3 120.1(3) . . ?
C4 C9 Cl3 119.4(3) . . ?
C4 O1 C3 117.3(3) . . ?
C10 N1 C10 110.9(3) 3_755 . ?
C10 N1 C14 110.79(18) 3_755 . ?
C10 N1 C14 107.03(17) . . ?
C10 N1 C14 107.03(17) 3_755 3_755 ?
C10 N1 C14 110.79(18) . 3_755 ?
C14 N1 C14 110.4(3) . 3_755 ?
N1 C10 C11 115.7(3) . . ?
N1 C10 H10A 108.4 . . ?
C11 C10 H10A 108.4 . . ?
N1 C10 H10B 108.4 . . ?
C11 C10 H10B 108.4 . . ?
H10A C10 H10B 107.4 . . ?
C10 C11 C12 111.0(3) . . ?
C10 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
C10 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C13 C12 C11 114.9(4) . . ?
C13 C12 H12A 108.5 . . ?
C11 C12 H12A 108.5 . . ?
C13 C12 H12B 108.5 . . ?
C11 C12 H12B 108.5 . . ?
H12A C12 H12B 107.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 N1 115.3(3) . . ?
C15 C14 H14A 108.5 . . ?
N1 C14 H14A 108.5 . . ?
C15 C14 H14B 108.5 . . ?
N1 C14 H14B 108.5 . . ?
H14A C14 H14B 107.5 . . ?
C16 C15 C14 112.0(3) . . ?
C16 C15 H15A 109.2 . . ?
C14 C15 H15A 109.2 . . ?
C16 C15 H15B 109.2 . . ?
C14 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
C15 C16 C17 113.6(4) . . ?
C15 C16 H16A 108.8 . . ?
C17 C16 H16A 108.8 . . ?
C15 C16 H16B 108.8 . . ?
C17 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C1 C2 C3 -70(21) . . . . ?
C1 C2 C3 O1 137(18) . . . . ?
O1 C4 C5 C6 179.6(4) . . . . ?
C9 C4 C5 C6 -0.6(6) . . . . ?
C4 C5 C6 C7 1.4(6) . . . . ?
C4 C5 C6 Cl1 -177.8(3) . . . . ?
C5 C6 C7 C8 -1.4(6) . . . . ?
Cl1 C6 C7 C8 177.7(3) . . . . ?
C5 C6 C7 Cl2 179.0(3) . . . . ?
Cl1 C6 C7 Cl2 -1.9(5) . . . . ?
C6 C7 C8 C9 0.7(6) . . . . ?
Cl2 C7 C8 C9 -179.7(3) . . . . ?
C7 C8 C9 C4 0.1(6) . . . . ?
C7 C8 C9 Cl3 179.5(3) . . . . ?
O1 C4 C9 C8 179.7(3) . . . . ?
C5 C4 C9 C8 -0.2(6) . . . . ?
O1 C4 C9 Cl3 0.2(5) . . . . ?
C5 C4 C9 Cl3 -179.6(3) . . . . ?
C9 C4 O1 C3 176.6(4) . . . . ?
C5 C4 O1 C3 -3.6(6) . . . . ?
C2 C3 O1 C4 -175.0(4) . . . . ?
C10 N1 C10 C11 -59.0(3) 3_755 . . . ?
C14 N1 C10 C11 -180.0(3) . . . . ?
C14 N1 C10 C11 59.7(4) 3_755 . . . ?
N1 C10 C11 C12 176.6(3) . . . . ?
C10 C11 C12 C13 -71.6(5) . . . . ?
C10 N1 C14 C15 58.9(4) 3_755 . . . ?
C10 N1 C14 C15 180.0(3) . . . . ?
C14 N1 C14 C15 -59.4(2) 3_755 . . . ?
N1 C14 C15 C16 177.1(3) . . . . ?
C14 C15 C16 C17 176.0(4) . . . . ?

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
C3 H3A Cl3 0.97 2.92 3.793(5) 150.9 4_566
C10 H10B I2 0.97 3.18 4.038(3) 149.1 .
C15 H15A Cl1 0.97 2.95 3.871(4) 159.0 4_566

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        29.25
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.013
_refine_diff_density_min         -0.858
_refine_diff_density_rms         0.075
_database_code_depnum_ccdc_archive 'CCDC 986302'
#######################################################################
#
#                 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_db02_b

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H4 Cl3 I O'
_chemical_formula_sum            'C9 H4 Cl3 I O'
_chemical_formula_weight         361.37

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'
Cl Cl 0.1484 0.1585 '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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'

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

_cell_length_a                   22.173(2)
_cell_length_b                   7.6870(7)
_cell_length_c                   13.8308(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 109.181(4)
_cell_angle_gamma                90.00
_cell_volume                     2226.5(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    9907
_cell_measurement_theta_min      2.82
_cell_measurement_theta_max      31.52

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.156
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1360
_exptl_absorpt_coefficient_mu    3.558
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_exptl_absorpt_correction_T_min  0.4138
_exptl_absorpt_correction_T_max  0.6348

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_decay_%        0.00
_diffrn_reflns_number            15765
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_av_sigmaI/netI    0.0192
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.94
_diffrn_reflns_theta_max         32.86
_reflns_number_total             3779
_reflns_number_gt                3174
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    
'SHELXS (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)'
_computing_structure_refinement  
'SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)'

_computing_molecular_graphics    
;
ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565)
Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., 
Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). 
J. Appl. Cryst. 39, 453-457
;
_computing_publication_material  SHELXL-97


_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0509P)²+5.6488P] 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         3779
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0452
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.1082
_refine_ls_wR_factor_gt          0.1035
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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 0.209045(12) -0.32737(3) 0.224459(18) 0.05276(10) Uani 1 1 d . . .
Cl1 Cl 0.11823(5) 0.52520(12) 0.43812(11) 0.0701(3) Uani 1 1 d . . .
Cl2 Cl -0.11050(4) 0.20836(14) 0.32414(8) 0.0552(2) Uani 1 1 d . . .
Cl3 Cl -0.04094(4) -0.15487(11) 0.34991(7) 0.04830(19) Uani 1 1 d . . .
O1 O 0.17007(9) 0.1814(3) 0.46161(17) 0.0382(4) Uani 1 1 d . . .
C1 C 0.20656(14) -0.1786(4) 0.3398(2) 0.0384(6) Uani 1 1 d . . .
C2 C 0.20548(13) -0.0886(4) 0.4088(2) 0.0366(5) Uani 1 1 d . . .
C3 C 0.20354(13) 0.0225(4) 0.4941(2) 0.0380(6) Uani 1 1 d . . .
H3A H 0.1832 -0.0411 0.5356 0.046 Uiso 1 1 calc R . .
H3B H 0.2469 0.0486 0.5368 0.046 Uiso 1 1 calc R . .
C4 C 0.10483(12) 0.1777(3) 0.4284(2) 0.0314(5) Uani 1 1 d . . .
C5 C 0.07408(15) 0.3369(4) 0.4155(3) 0.0388(6) Uani 1 1 d . . .
C6 C 0.00777(16) 0.3454(4) 0.3838(3) 0.0422(6) Uani 1 1 d . . .
H6 H -0.0125 0.4529 0.3758 0.051 Uiso 1 1 calc R . .
C7 C -0.02818(14) 0.1934(4) 0.3642(2) 0.0368(6) Uani 1 1 d . . .
C8 C 0.00203(13) 0.0350(4) 0.3758(2) 0.0334(5) Uani 1 1 d . . .
C9 C 0.06874(13) 0.0258(4) 0.4080(2) 0.0324(5) Uani 1 1 d . . .
H9 H 0.0889 -0.0818 0.4157 0.039 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 1.978(3) . ?
Cl1 C5 1.717(3) . ?
Cl2 C7 1.728(3) . ?
Cl3 C8 1.715(3) . ?
O1 C4 1.367(3) . ?
O1 C3 1.423(3) . ?
C1 C2 1.186(4) . ?
C2 C3 1.468(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.384(4) . ?
C4 C9 1.391(4) . ?
C5 C6 1.391(4) . ?
C6 C7 1.390(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.374(4) . ?
C8 C9 1.399(4) . ?
C9 H9 0.9300 . ?

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 O1 C3 118.2(2) . . ?
C2 C1 I1 179.4(3) . . ?
C1 C2 C3 179.5(3) . . ?
O1 C3 C2 113.3(2) . . ?
O1 C3 H3A 108.9 . . ?
C2 C3 H3A 108.9 . . ?
O1 C3 H3B 108.9 . . ?
C2 C3 H3B 108.9 . . ?
H3A C3 H3B 107.7 . . ?
O1 C4 C5 116.6(2) . . ?
O1 C4 C9 124.1(2) . . ?
C5 C4 C9 119.3(2) . . ?
C4 C5 C6 120.5(3) . . ?
C4 C5 Cl1 119.6(2) . . ?
C6 C5 Cl1 119.9(2) . . ?
C7 C6 C5 120.1(3) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
C8 C7 C6 119.7(3) . . ?
C8 C7 Cl2 121.3(2) . . ?
C6 C7 Cl2 119.0(2) . . ?
C7 C8 C9 120.4(3) . . ?
C7 C8 Cl3 120.9(2) . . ?
C9 C8 Cl3 118.7(2) . . ?
C4 C9 C8 120.0(2) . . ?
C4 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?

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
C4 O1 C3 C2 78.5(3) . . . . ?
C3 O1 C4 C5 168.4(3) . . . . ?
C3 O1 C4 C9 -11.2(4) . . . . ?
O1 C4 C5 C6 -178.7(3) . . . . ?
C9 C4 C5 C6 1.0(4) . . . . ?
O1 C4 C5 Cl1 1.6(4) . . . . ?
C9 C4 C5 Cl1 -178.7(2) . . . . ?
C4 C5 C6 C7 -0.5(5) . . . . ?
Cl1 C5 C6 C7 179.2(3) . . . . ?
C5 C6 C7 C8 -0.2(5) . . . . ?
C5 C6 C7 Cl2 -179.5(3) . . . . ?
C6 C7 C8 C9 0.5(4) . . . . ?
Cl2 C7 C8 C9 179.8(2) . . . . ?
C6 C7 C8 Cl3 -178.8(2) . . . . ?
Cl2 C7 C8 Cl3 0.5(3) . . . . ?
O1 C4 C9 C8 178.9(2) . . . . ?
C5 C4 C9 C8 -0.7(4) . . . . ?
C7 C8 C9 C4 0.0(4) . . . . ?
Cl3 C8 C9 C4 179.3(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.910
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.126
_refine_diff_density_min         -1.001
_refine_diff_density_rms         0.100

_database_code_depnum_ccdc_archive 'CCDC 986303'
#######################################################################
#
#                 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_db27_b

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H4 Cl3 I O'
_chemical_formula_sum            'C9 H4 Cl3 I O'
_chemical_formula_weight         361.37

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'
O O 0.0106 0.0060 '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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

_cell_length_a                   4.2659(6)
_cell_length_b                   10.4936(14)
_cell_length_c                   13.3814(16)
_cell_angle_alpha                108.226(12)
_cell_angle_beta                 93.893(12)
_cell_angle_gamma                90.291(12)
_cell_volume                     567.43(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7878
_cell_measurement_theta_min      2.14
_cell_measurement_theta_max      27.73
_exptl_crystal_description       lamina
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.115
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             340
_exptl_absorpt_coefficient_mu    3.490
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.'
_exptl_absorpt_correction_T_min  0.5823
_exptl_absorpt_correction_T_max  0.7452

_exptl_special_details           
; 
 II stable polymorph. 
From a solution with haloprogin/NaC2H4O2 ratio 1:2
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker, APEX 2000, CCD area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_standards_decay_%        0.00
_diffrn_reflns_number            13209
_diffrn_reflns_av_R_equivalents  0.0652
_diffrn_reflns_av_sigmaI/netI    0.0293
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         27.75
_reflns_number_total             2461
_reflns_number_gt                2108
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    
'SHELXS (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)'
_computing_structure_refinement  
'SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)'

_computing_molecular_graphics    
;
ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565)
Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., 
Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). 
J. Appl. Cryst. 39, 453-457
;
_computing_publication_material  SHELXL-97


_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0478P)²+0.0745P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    riding
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2461
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0314
_refine_ls_wR_factor_ref         0.0785
_refine_ls_wR_factor_gt          0.0737
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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 0.74485(5) 0.81036(2) 0.942848(16) 0.05704(11) Uani 1 1 d . . .
Cl1 Cl 0.3835(2) 0.17375(9) 0.47599(7) 0.0640(2) Uani 1 1 d . . .
Cl2 Cl -0.1473(3) 0.07047(11) 0.79543(8) 0.0768(3) Uani 1 1 d . . .
Cl3 Cl -0.2817(2) 0.38025(11) 0.89295(7) 0.0655(2) Uani 1 1 d . . .
O1 O 0.2714(5) 0.4492(2) 0.58597(15) 0.0461(5) Uani 1 1 d . . .
C1 C 0.5191(7) 0.7195(3) 0.8030(3) 0.0464(7) Uani 1 1 d . . .
C2 C 0.3801(7) 0.6627(3) 0.7223(3) 0.0458(7) Uani 1 1 d . . .
C3 C 0.2019(7) 0.5891(3) 0.6223(2) 0.0474(7) Uani 1 1 d . . .
H3A H -0.0212 0.5983 0.6319 0.057 Uiso 1 1 calc R . .
H3B H 0.2496 0.6293 0.5688 0.057 Uiso 1 1 calc R . .
C4 C 0.1634(6) 0.3685(3) 0.6386(2) 0.0407(6) Uani 1 1 d . . .
C5 C 0.2128(7) 0.2320(3) 0.5949(2) 0.0450(7) Uani 1 1 d . . .
C6 C 0.1183(8) 0.1417(3) 0.6437(3) 0.0525(8) Uani 1 1 d . . .
H6 H 0.1565 0.0508 0.6145 0.063 Uiso 1 1 calc R . .
C7 C -0.0329(8) 0.1861(3) 0.7360(3) 0.0509(7) Uani 1 1 d . . .
C8 C -0.0894(7) 0.3205(3) 0.7785(2) 0.0451(7) Uani 1 1 d . . .
C9 C 0.0082(7) 0.4119(3) 0.7307(2) 0.0441(6) Uani 1 1 d . . .
H9 H -0.0305 0.5027 0.7603 0.053 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 1.992(3) . ?
Cl1 C5 1.729(3) . ?
Cl2 C7 1.730(3) . ?
Cl3 C8 1.728(3) . ?
O1 C4 1.356(3) . ?
O1 C3 1.435(4) . ?
C1 C2 1.175(4) . ?
C2 C3 1.474(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C9 1.388(4) . ?
C4 C5 1.390(4) . ?
C5 C6 1.381(4) . ?
C6 C7 1.382(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.376(5) . ?
C8 C9 1.386(4) . ?
C9 H9 0.9300 . ?

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 O1 C3 118.5(2) . . ?
C2 C1 I1 177.4(3) . . ?
C1 C2 C3 178.5(3) . . ?
O1 C3 C2 113.0(2) . . ?
O1 C3 H3A 109.0 . . ?
C2 C3 H3A 109.0 . . ?
O1 C3 H3B 109.0 . . ?
C2 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
O1 C4 C9 125.1(3) . . ?
O1 C4 C5 116.2(3) . . ?
C9 C4 C5 118.7(3) . . ?
C6 C5 C4 120.8(3) . . ?
C6 C5 Cl1 119.4(3) . . ?
C4 C5 Cl1 119.7(2) . . ?
C5 C6 C7 120.0(3) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 119.6(3) . . ?
C8 C7 Cl2 121.5(3) . . ?
C6 C7 Cl2 118.9(3) . . ?
C7 C8 C9 120.6(3) . . ?
C7 C8 Cl3 121.2(2) . . ?
C9 C8 Cl3 118.2(3) . . ?
C8 C9 C4 120.2(3) . . ?
C8 C9 H9 119.9 . . ?
C4 C9 H9 119.9 . . ?

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
I1 C1 C2 C3 -3(18) . . . . ?
C4 O1 C3 C2 71.9(3) . . . . ?
C1 C2 C3 O1 -60(13) . . . . ?
C3 O1 C4 C9 -5.0(4) . . . . ?
C3 O1 C4 C5 174.5(2) . . . . ?
O1 C4 C5 C6 178.5(3) . . . . ?
C9 C4 C5 C6 -2.0(4) . . . . ?
O1 C4 C5 Cl1 -3.5(4) . . . . ?
C9 C4 C5 Cl1 176.0(2) . . . . ?
C4 C5 C6 C7 1.3(5) . . . . ?
Cl1 C5 C6 C7 -176.7(3) . . . . ?
C5 C6 C7 C8 0.2(5) . . . . ?
C5 C6 C7 Cl2 -179.8(2) . . . . ?
C6 C7 C8 C9 -1.0(5) . . . . ?
Cl2 C7 C8 C9 179.0(2) . . . . ?
C6 C7 C8 Cl3 179.3(2) . . . . ?
Cl2 C7 C8 Cl3 -0.7(4) . . . . ?
C7 C8 C9 C4 0.3(4) . . . . ?
Cl3 C8 C9 C4 -180.0(2) . . . . ?
O1 C4 C9 C8 -179.3(3) . . . . ?
C5 C4 C9 C8 1.2(4) . . . . ?

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
C3 H3B Cl1 0.97 2.82 3.657(3) 145.0 2_666

_diffrn_measured_fraction_theta_max 0.918
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.609
_refine_diff_density_min         -0.993
_refine_diff_density_rms         0.135
_database_code_depnum_ccdc_archive 'CCDC 986304'
#######################################################################
#
#                 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_db27_a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H3 Cl3 I O'
_chemical_formula_sum            'C9 H3 Cl3 I O'
_chemical_formula_weight         360.36

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'
O O 0.0106 0.0060 '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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

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

_cell_length_a                   31.100(5)
_cell_length_b                   5.3807(7)
_cell_length_c                   13.861(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.050(5)
_cell_angle_gamma                90.00
_cell_volume                     2217.5(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    885
_cell_measurement_theta_min      3.85
_cell_measurement_theta_max      27.19
_exptl_crystal_description       needle
_exptl_crystal_colour            ?
_exptl_crystal_size_min          0.07
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_max          0.37
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.159
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1352
_exptl_absorpt_coefficient_mu    3.572
_exptl_absorpt_correction_type   none

_exptl_special_details           
; 
 The crystal was instable: during the data collection there was a fast
phase transition with formation of a crystal powder. Only partial data
having very low quality, as demonstred by the high Rave were collected.
In spite of that there was no problem to solve the structure.
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2364
_diffrn_reflns_av_R_equivalents  0.2267
_diffrn_reflns_av_sigmaI/netI    0.1285
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.74
_diffrn_reflns_theta_max         24.99
_reflns_number_total             1634
_reflns_number_gt                1041
_reflns_threshold_expression     'I > 2σ(I)'

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    
'SHELXS (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)'
_computing_structure_refinement  
'SHELXL-97 (Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122)'

_computing_molecular_graphics    
;
ORTEP-3 (Farrugia, L.J. (1997) Jour. Appl. Cryst. 30, 565)
Mercury (Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., 
Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). 
J. Appl. Cryst. 39, 453-457
;
_computing_publication_material  SHELXL-97


_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    noref
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0008(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1634
_refine_ls_number_parameters     128
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1436
_refine_ls_R_factor_gt           0.1236
_refine_ls_wR_factor_ref         0.2992
_refine_ls_wR_factor_gt          0.2744
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.55316(4) 0.50208(16) 0.38794(7) 0.0562(7) Uani 1 1 d . . .
Cl1 Cl 0.35308(15) -0.1229(7) 0.0547(3) 0.0617(13) Uani 1 1 d . . .
Cl2 Cl 0.25968(16) 0.6279(8) 0.1485(3) 0.0692(14) Uani 1 1 d . . .
Cl3 Cl 0.32934(17) 0.6467(7) 0.3686(3) 0.0656(13) Uani 1 1 d . . .
C1 C 0.5038(5) 0.256(3) 0.3816(9) 0.048(4) Uani 1 1 d . . .
C2 C 0.4755(5) 0.108(3) 0.3725(9) 0.044(4) Uani 1 1 d . . .
C3 C 0.4414(6) -0.086(3) 0.3585(10) 0.064(5) Uani 1 1 d . . .
H3A H 0.4560 -0.2469 0.3700 0.077 Uiso 1 1 calc R . .
H3B H 0.4252 -0.0638 0.4080 0.077 Uiso 1 1 calc R . .
O1 O 0.4100(4) -0.0814(18) 0.2596(7) 0.053(3) Uani 1 1 d . . .
C4 C 0.3760(5) 0.093(2) 0.2375(9) 0.043(4) Uani 1 1 d . . .
C5 C 0.3468(5) 0.090(2) 0.1417(10) 0.046(4) Uani 1 1 d . . .
C6 C 0.3105(5) 0.253(2) 0.1164(9) 0.050(4) Uani 1 1 d . . .
H6 H 0.2902 0.2461 0.0520 0.060 Uiso 1 1 calc R . .
C7 C 0.3040(5) 0.422(3) 0.1835(10) 0.050(4) Uani 1 1 d . . .
C8 C 0.3345(5) 0.436(2) 0.2795(10) 0.042(4) Uani 1 1 d . . .
C9 C 0.3714(5) 0.269(2) 0.3059(9) 0.049(4) Uani 1 1 d . . .
H9 H 0.3924 0.2791 0.3692 0.059 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.010(17) . ?
Cl1 C5 1.717(14) . ?
Cl2 C7 1.724(17) . ?
Cl3 C8 1.720(14) . ?
C1 C2 1.17(2) . ?
C2 C3 1.46(2) . ?
C3 O1 1.431(16) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
O1 C4 1.380(17) . ?
C4 C5 1.372(18) . ?
C4 C9 1.379(19) . ?
C5 C6 1.39(2) . ?
C6 C7 1.36(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.392(19) . ?
C8 C9 1.41(2) . ?
C9 H9 0.9300 . ?

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 I1 175.7(14) . . ?
C1 C2 C3 177.3(19) . . ?
O1 C3 C2 112.4(12) . . ?
O1 C3 H3A 109.1 . . ?
C2 C3 H3A 109.1 . . ?
O1 C3 H3B 109.1 . . ?
C2 C3 H3B 109.1 . . ?
H3A C3 H3B 107.9 . . ?
C4 O1 C3 119.1(12) . . ?
C5 C4 C9 119.9(13) . . ?
C5 C4 O1 117.1(12) . . ?
C9 C4 O1 122.9(11) . . ?
C4 C5 C6 119.8(13) . . ?
C4 C5 Cl1 120.4(11) . . ?
C6 C5 Cl1 119.7(10) . . ?
C7 C6 C5 121.4(12) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C8 119.7(15) . . ?
C6 C7 Cl2 120.3(11) . . ?
C8 C7 Cl2 120.0(12) . . ?
C7 C8 C9 119.1(14) . . ?
C7 C8 Cl3 122.7(12) . . ?
C9 C8 Cl3 118.1(9) . . ?
C4 C9 C8 119.9(11) . . ?
C4 C9 H9 120.1 . . ?
C8 C9 H9 120.1 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 C1 C2 C3 27(43) . . . . ?
C1 C2 C3 O1 -80(31) . . . . ?
C2 C3 O1 C4 -78.7(19) . . . . ?
C3 O1 C4 C5 179.9(14) . . . . ?
C3 O1 C4 C9 2(2) . . . . ?
C9 C4 C5 C6 -5(2) . . . . ?
O1 C4 C5 C6 176.8(14) . . . . ?
C9 C4 C5 Cl1 178.2(12) . . . . ?
O1 C4 C5 Cl1 0.1(19) . . . . ?
C4 C5 C6 C7 2(2) . . . . ?
Cl1 C5 C6 C7 179.1(12) . . . . ?
C5 C6 C7 C8 1(2) . . . . ?
C5 C6 C7 Cl2 178.0(11) . . . . ?
C6 C7 C8 C9 -1(2) . . . . ?
Cl2 C7 C8 C9 -178.4(11) . . . . ?
C6 C7 C8 Cl3 179.2(11) . . . . ?
Cl2 C7 C8 Cl3 1.9(18) . . . . ?
C5 C4 C9 C8 5(2) . . . . ?
O1 C4 C9 C8 -177.4(13) . . . . ?
C7 C8 C9 C4 -2(2) . . . . ?
Cl3 C8 C9 C4 178.1(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.835
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.835
_refine_diff_density_max         4.982
_refine_diff_density_min         -1.631
_refine_diff_density_rms         0.439
_database_code_depnum_ccdc_archive 'CCDC 986305'
