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


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#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
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# 
#  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 
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data_p-1
_database_code_depnum_ccdc_archive 'CCDC 861376'
#TrackingRef 'web_deposit_cif_file_0_Hai-TaoZhu_1325906579.P-1.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H13 I O2'
_chemical_formula_weight         436.22

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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                   9.369(2)
_cell_length_b                   9.971(2)
_cell_length_c                   10.815(4)
_cell_angle_alpha                98.526(3)
_cell_angle_beta                 93.088(3)
_cell_angle_gamma                117.892(2)
_cell_volume                     874.3(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3595
_cell_measurement_theta_min      2.36
_cell_measurement_theta_max      28.25

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.657
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             428
_exptl_absorpt_coefficient_mu    1.843
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6765
_exptl_absorpt_correction_T_max  0.7209
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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       '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6204
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0352
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         25.50
_reflns_number_total             3182
_reflns_number_gt                2771
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_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^)+(0.0205P)^2^+0.7985P] 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         3182
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0356
_refine_ls_R_factor_gt           0.0278
_refine_ls_wR_factor_ref         0.0624
_refine_ls_wR_factor_gt          0.0593
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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 0.1958(4) 0.0158(4) 0.0343(3) 0.0303(7) Uani 1 1 d . . .
C2 C 0.2373(4) 0.1730(4) 0.0201(3) 0.0291(7) Uani 1 1 d . . .
C3 C 0.2196(4) 0.2267(4) -0.0878(3) 0.0406(8) Uani 1 1 d . . .
H3 H 0.1816 0.1612 -0.1666 0.049 Uiso 1 1 calc R . .
C4 C 0.2598(5) 0.3792(5) -0.0741(3) 0.0468(9) Uani 1 1 d . . .
H4 H 0.2490 0.4185 -0.1448 0.056 Uiso 1 1 calc R . .
C5 C 0.3163(4) 0.4756(4) 0.0431(3) 0.0438(9) Uani 1 1 d . . .
H5 H 0.3428 0.5789 0.0499 0.053 Uiso 1 1 calc R . .
C6 C 0.3346(4) 0.4227(4) 0.1507(3) 0.0359(8) Uani 1 1 d . . .
H6 H 0.3732 0.4885 0.2294 0.043 Uiso 1 1 calc R . .
C7 C 0.2934(4) 0.2688(4) 0.1370(3) 0.0270(7) Uani 1 1 d . . .
C8 C 0.2931(4) 0.1755(3) 0.2341(3) 0.0271(7) Uani 1 1 d . . .
C9 C 0.1992(4) 0.1818(3) 0.3427(3) 0.0260(6) Uani 1 1 d . . .
C10 C 0.0437(4) 0.1603(4) 0.3405(3) 0.0316(7) Uani 1 1 d . . .
H10 H -0.0215 0.1374 0.2643 0.038 Uiso 1 1 calc R . .
C11 C -0.0146(4) 0.1732(4) 0.4545(3) 0.0354(8) Uani 1 1 d . . .
H11 H -0.1209 0.1564 0.4551 0.043 Uiso 1 1 calc R . .
C12 C 0.0847(4) 0.2110(4) 0.5671(3) 0.0359(8) Uani 1 1 d . . .
H12 H 0.0440 0.2191 0.6428 0.043 Uiso 1 1 calc R . .
C13 C 0.2433(4) 0.2369(4) 0.5696(3) 0.0332(7) Uani 1 1 d . . .
H13 H 0.3102 0.2646 0.6460 0.040 Uiso 1 1 calc R . .
C14 C 0.3003(4) 0.2208(3) 0.4561(3) 0.0258(6) Uani 1 1 d . . .
C15 C 0.4623(4) 0.2419(3) 0.4294(3) 0.0255(6) Uani 1 1 d . . .
C16 C 0.4583(4) 0.2172(3) 0.3038(3) 0.0283(7) Uani 1 1 d . . .
C17 C 0.5956(4) 0.2791(3) 0.5300(3) 0.0279(7) Uani 1 1 d . . .
C18 C 0.5677(4) 0.1876(4) 0.6205(3) 0.0380(8) Uani 1 1 d . . .
H18 H 0.4658 0.1019 0.6165 0.046 Uiso 1 1 calc R . .
C19 C 0.6900(5) 0.2230(5) 0.7160(3) 0.0487(10) Uani 1 1 d . . .
H19 H 0.6710 0.1602 0.7755 0.058 Uiso 1 1 calc R . .
C20 C 0.8392(5) 0.3500(5) 0.7240(3) 0.0503(10) Uani 1 1 d . . .
H20 H 0.9208 0.3745 0.7897 0.060 Uiso 1 1 calc R . .
C21 C 0.8691(4) 0.4413(5) 0.6356(3) 0.0455(9) Uani 1 1 d . . .
H21 H 0.9712 0.5272 0.6408 0.055 Uiso 1 1 calc R . .
C22 C 0.7476(4) 0.4061(4) 0.5386(3) 0.0351(8) Uani 1 1 d . . .
H22 H 0.7685 0.4683 0.4786 0.042 Uiso 1 1 calc R . .
I1 I 0.63468(3) 0.20511(3) 0.20211(2) 0.04340(9) Uani 1 1 d . . .
O1 O 0.1464(3) -0.1017(3) -0.0421(2) 0.0440(6) Uani 1 1 d . . .
O2 O 0.2213(3) 0.0178(2) 0.16056(18) 0.0309(5) Uani 1 1 d . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0264(17) 0.0417(19) 0.0208(15) 0.0049(14) 0.0038(13) 0.0150(15)
C2 0.0274(17) 0.0402(18) 0.0203(15) 0.0094(13) 0.0056(12) 0.0156(15)
C3 0.045(2) 0.054(2) 0.0210(16) 0.0129(15) 0.0033(15) 0.0207(18)
C4 0.054(2) 0.062(3) 0.0339(19) 0.0284(18) 0.0096(17) 0.029(2)
C5 0.053(2) 0.042(2) 0.045(2) 0.0195(17) 0.0152(18) 0.0256(19)
C6 0.041(2) 0.0387(19) 0.0284(17) 0.0076(14) 0.0081(15) 0.0195(17)
C7 0.0266(16) 0.0375(18) 0.0217(15) 0.0104(13) 0.0058(12) 0.0179(14)
C8 0.0289(17) 0.0342(17) 0.0184(14) 0.0041(13) -0.0001(12) 0.0162(14)
C9 0.0293(17) 0.0279(16) 0.0222(15) 0.0095(12) 0.0064(13) 0.0133(14)
C10 0.0312(18) 0.0350(18) 0.0269(16) 0.0060(14) 0.0002(14) 0.0150(15)
C11 0.0292(18) 0.0408(19) 0.0400(19) 0.0121(15) 0.0097(15) 0.0182(16)
C12 0.039(2) 0.047(2) 0.0280(17) 0.0133(15) 0.0140(15) 0.0229(17)
C13 0.0396(19) 0.0418(19) 0.0209(15) 0.0098(14) 0.0040(14) 0.0207(16)
C14 0.0292(17) 0.0288(16) 0.0204(14) 0.0090(12) 0.0035(12) 0.0136(14)
C15 0.0280(16) 0.0247(16) 0.0232(15) 0.0074(12) 0.0020(12) 0.0115(14)
C16 0.0276(17) 0.0332(17) 0.0264(16) 0.0089(13) 0.0053(13) 0.0156(14)
C17 0.0316(17) 0.0309(17) 0.0236(15) 0.0032(13) -0.0005(13) 0.0181(15)
C18 0.046(2) 0.0345(18) 0.0358(18) 0.0115(15) -0.0004(15) 0.0202(17)
C19 0.070(3) 0.055(2) 0.035(2) 0.0122(18) -0.0044(19) 0.043(2)
C20 0.053(3) 0.073(3) 0.0327(19) -0.0086(19) -0.0154(17) 0.045(2)
C21 0.0292(19) 0.053(2) 0.048(2) -0.0063(18) -0.0036(16) 0.0202(18)
C22 0.0356(19) 0.0370(19) 0.0338(17) 0.0078(15) 0.0041(15) 0.0182(16)
I1 0.03954(15) 0.06280(18) 0.03542(13) 0.01414(11) 0.01183(10) 0.02882(12)
O1 0.0504(15) 0.0457(15) 0.0289(12) -0.0028(11) 0.0016(11) 0.0206(13)
O2 0.0399(13) 0.0335(12) 0.0219(10) 0.0066(9) 0.0014(9) 0.0198(11)

_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 O1 1.198(4) . ?
C1 O2 1.369(3) . ?
C1 C2 1.463(5) . ?
C2 C7 1.374(4) . ?
C2 C3 1.387(4) . ?
C3 C4 1.367(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.378(4) . ?
C6 H6 0.9300 . ?
C7 C8 1.502(4) . ?
C8 O2 1.462(3) . ?
C8 C9 1.517(4) . ?
C8 C16 1.522(4) . ?
C9 C10 1.367(4) . ?
C9 C14 1.394(4) . ?
C10 C11 1.388(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.379(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.382(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.382(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.482(4) . ?
C15 C16 1.340(4) . ?
C15 C17 1.477(4) . ?
C16 I1 2.073(3) . ?
C17 C22 1.380(4) . ?
C17 C18 1.389(4) . ?
C18 C19 1.375(5) . ?
C18 H18 0.9300 . ?
C19 C20 1.365(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.367(5) . ?
C20 H20 0.9300 . ?
C21 C22 1.381(5) . ?
C21 H21 0.9300 . ?
C22 H22 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
O1 C1 O2 121.0(3) . . ?
O1 C1 C2 131.4(3) . . ?
O2 C1 C2 107.7(2) . . ?
C7 C2 C3 121.6(3) . . ?
C7 C2 C1 109.0(3) . . ?
C3 C2 C1 129.3(3) . . ?
C4 C3 C2 117.6(3) . . ?
C4 C3 H3 121.2 . . ?
C2 C3 H3 121.2 . . ?
C3 C4 C5 120.8(3) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 121.7(3) . . ?
C4 C5 H5 119.1 . . ?
C6 C5 H5 119.1 . . ?
C7 C6 C5 117.5(3) . . ?
C7 C6 H6 121.3 . . ?
C5 C6 H6 121.3 . . ?
C2 C7 C6 120.8(3) . . ?
C2 C7 C8 108.7(3) . . ?
C6 C7 C8 130.5(3) . . ?
O2 C8 C7 103.4(2) . . ?
O2 C8 C9 110.7(2) . . ?
C7 C8 C9 115.9(2) . . ?
O2 C8 C16 108.5(2) . . ?
C7 C8 C16 116.7(3) . . ?
C9 C8 C16 101.7(2) . . ?
C10 C9 C14 121.5(3) . . ?
C10 C9 C8 129.6(3) . . ?
C14 C9 C8 108.8(3) . . ?
C9 C10 C11 118.5(3) . . ?
C9 C10 H10 120.7 . . ?
C11 C10 H10 120.7 . . ?
C12 C11 C10 120.2(3) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C11 C12 C13 121.4(3) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C14 C13 C12 118.5(3) . . ?
C14 C13 H13 120.8 . . ?
C12 C13 H13 120.8 . . ?
C13 C14 C9 119.9(3) . . ?
C13 C14 C15 130.6(3) . . ?
C9 C14 C15 109.5(2) . . ?
C16 C15 C17 129.5(3) . . ?
C16 C15 C14 107.7(3) . . ?
C17 C15 C14 122.7(2) . . ?
C15 C16 C8 112.3(3) . . ?
C15 C16 I1 127.8(2) . . ?
C8 C16 I1 119.4(2) . . ?
C22 C17 C18 118.6(3) . . ?
C22 C17 C15 121.5(3) . . ?
C18 C17 C15 119.9(3) . . ?
C19 C18 C17 120.4(3) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C18 120.3(4) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 120.2(3) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C20 C21 C22 120.0(4) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C17 C22 C21 120.5(3) . . ?
C17 C22 H22 119.7 . . ?
C21 C22 H22 119.7 . . ?
C1 O2 C8 110.9(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
O1 C1 C2 C7 -178.3(3) . . . . ?
O2 C1 C2 C7 2.4(3) . . . . ?
O1 C1 C2 C3 5.0(6) . . . . ?
O2 C1 C2 C3 -174.4(3) . . . . ?
C7 C2 C3 C4 0.0(5) . . . . ?
C1 C2 C3 C4 176.4(3) . . . . ?
C2 C3 C4 C5 0.1(5) . . . . ?
C3 C4 C5 C6 0.1(6) . . . . ?
C4 C5 C6 C7 -0.3(5) . . . . ?
C3 C2 C7 C6 -0.3(5) . . . . ?
C1 C2 C7 C6 -177.3(3) . . . . ?
C3 C2 C7 C8 178.0(3) . . . . ?
C1 C2 C7 C8 1.0(3) . . . . ?
C5 C6 C7 C2 0.4(5) . . . . ?
C5 C6 C7 C8 -177.4(3) . . . . ?
C2 C7 C8 O2 -3.7(3) . . . . ?
C6 C7 C8 O2 174.3(3) . . . . ?
C2 C7 C8 C9 -125.0(3) . . . . ?
C6 C7 C8 C9 53.0(4) . . . . ?
C2 C7 C8 C16 115.3(3) . . . . ?
C6 C7 C8 C16 -66.6(4) . . . . ?
O2 C8 C9 C10 -67.4(4) . . . . ?
C7 C8 C9 C10 49.9(4) . . . . ?
C16 C8 C9 C10 177.5(3) . . . . ?
O2 C8 C9 C14 114.7(3) . . . . ?
C7 C8 C9 C14 -128.0(3) . . . . ?
C16 C8 C9 C14 -0.4(3) . . . . ?
C14 C9 C10 C11 -2.0(5) . . . . ?
C8 C9 C10 C11 -179.7(3) . . . . ?
C9 C10 C11 C12 1.6(5) . . . . ?
C10 C11 C12 C13 0.1(5) . . . . ?
C11 C12 C13 C14 -1.5(5) . . . . ?
C12 C13 C14 C9 1.1(5) . . . . ?
C12 C13 C14 C15 179.5(3) . . . . ?
C10 C9 C14 C13 0.6(5) . . . . ?
C8 C9 C14 C13 178.7(3) . . . . ?
C10 C9 C14 C15 -178.1(3) . . . . ?
C8 C9 C14 C15 0.1(3) . . . . ?
C13 C14 C15 C16 -178.1(3) . . . . ?
C9 C14 C15 C16 0.4(3) . . . . ?
C13 C14 C15 C17 3.4(5) . . . . ?
C9 C14 C15 C17 -178.1(3) . . . . ?
C17 C15 C16 C8 177.7(3) . . . . ?
C14 C15 C16 C8 -0.7(3) . . . . ?
C17 C15 C16 I1 5.4(5) . . . . ?
C14 C15 C16 I1 -173.0(2) . . . . ?
O2 C8 C16 C15 -116.0(3) . . . . ?
C7 C8 C16 C15 127.7(3) . . . . ?
C9 C8 C16 C15 0.7(3) . . . . ?
O2 C8 C16 I1 57.0(3) . . . . ?
C7 C8 C16 I1 -59.2(3) . . . . ?
C9 C8 C16 I1 173.70(19) . . . . ?
C16 C15 C17 C22 56.5(5) . . . . ?
C14 C15 C17 C22 -125.5(3) . . . . ?
C16 C15 C17 C18 -125.2(4) . . . . ?
C14 C15 C17 C18 52.9(4) . . . . ?
C22 C17 C18 C19 -0.3(5) . . . . ?
C15 C17 C18 C19 -178.7(3) . . . . ?
C17 C18 C19 C20 1.1(5) . . . . ?
C18 C19 C20 C21 -1.2(5) . . . . ?
C19 C20 C21 C22 0.6(5) . . . . ?
C18 C17 C22 C21 -0.3(5) . . . . ?
C15 C17 C22 C21 178.1(3) . . . . ?
C20 C21 C22 C17 0.1(5) . . . . ?
O1 C1 O2 C8 175.7(3) . . . . ?
C2 C1 O2 C8 -4.9(3) . . . . ?
C7 C8 O2 C1 5.3(3) . . . . ?
C9 C8 O2 C1 130.1(2) . . . . ?
C16 C8 O2 C1 -119.2(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.980
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.980
_refine_diff_density_max         0.457
_refine_diff_density_min         -0.490
_refine_diff_density_rms         0.068




data_test_0m
_database_code_depnum_ccdc_archive 'CCDC 893622'
#TrackingRef 'test_0m.cif'

_audit_creation_date             2011-11-04
_audit_creation_method           
;
Olex2 1.1
(compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
?
;
_chemical_formula_moiety         'C12 H9 I O2'
_chemical_formula_sum            'C12 H9 I O2'
_chemical_formula_weight         312.09
_chemical_melting_point          ?
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'
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           14
_space_group_name_H-M_alt        'P 1 21/a 1'
_space_group_name_Hall           '-P 2yab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, y+1/2, -z'
3 '-x, -y, -z'
4 'x-1/2, -y-1/2, z'

_cell_length_a                   7.714(4)
_cell_length_b                   18.219(10)
_cell_length_c                   8.198(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.004(5)
_cell_angle_gamma                90.00
_cell_volume                     1143.5(11)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3411
_cell_measurement_temperature    569(2)
_cell_measurement_theta_max      25.422
_cell_measurement_theta_min      2.503
_exptl_absorpt_coefficient_mu    2.777
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.3791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
R(int) was 0.1233 before and 0.0501 after correction.
The Ratio of minimum to maximum transmission is 0.508313220703.
The \l/2 correction factor is Not present
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.813
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
?
;
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_unetI/netI     0.0379
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7990
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.24
_diffrn_ambient_temperature      569(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'MO K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_reflns_number_gt                1603
_reflns_number_total             2120
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.60A (Bruker, 2009)'
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.736
_refine_diff_density_min         -1.134
_refine_diff_density_rms         0.110
_refine_ls_extinction_coef       0.072(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0410
_refine_ls_restrained_S_all      1.060
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0216P)^2^+3.1433P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0850
_refine_ls_wR_factor_ref         0.0972
_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.
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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 0.3621(6) 0.6436(2) 0.3803(6) 0.0396(11) Uani 1 1 d . . .
C2 C 0.4980(6) 0.6103(2) 0.4923(5) 0.0384(11) Uani 1 1 d . . .
C3 C 0.5059(8) 0.6098(3) 0.6642(6) 0.0547(14) Uani 1 1 d . . .
H3 H 0.4179 0.6322 0.7143 0.066 Uiso 1 1 calc R . .
C4 C 0.6427(9) 0.5767(3) 0.7585(7) 0.0668(17) Uani 1 1 d . . .
H4 H 0.6459 0.5769 0.8723 0.080 Uiso 1 1 calc R . .
C5 C 0.7749(8) 0.5432(3) 0.6889(7) 0.0643(16) Uani 1 1 d . . .
H5 H 0.8666 0.5210 0.7551 0.077 Uiso 1 1 calc R . .
C6 C 0.7712(7) 0.5426(3) 0.5219(6) 0.0537(13) Uani 1 1 d . . .
H6 H 0.8601 0.5197 0.4737 0.064 Uiso 1 1 calc R . .
C7 C 0.6348(6) 0.5760(2) 0.4251(5) 0.0382(10) Uani 1 1 d . . .
C8 C 0.6374(7) 0.5741(3) 0.2470(6) 0.0460(12) Uani 1 1 d . . .
C9 C 0.3671(6) 0.6425(2) 0.2187(6) 0.0391(10) Uani 1 1 d . . .
C10 C 0.2427(7) 0.6735(3) 0.0837(6) 0.0488(12) Uani 1 1 d . . .
C11 C 0.2468(9) 0.7447(4) 0.0546(9) 0.081(2) Uani 1 1 d . . .
H11A H 0.1713 0.7650 -0.0305 0.098 Uiso 1 1 calc R . .
H11B H 0.3254 0.7746 0.1192 0.098 Uiso 1 1 calc R . .
C12 C 0.1239(8) 0.6205(4) -0.0105(7) 0.0706(17) Uani 1 1 d . . .
H12A H 0.1909 0.5808 -0.0477 0.106 Uiso 1 1 calc R . .
H12B H 0.0611 0.6448 -0.1035 0.106 Uiso 1 1 calc R . .
H12C H 0.0426 0.6016 0.0588 0.106 Uiso 1 1 calc R . .
I1 I 0.15074(6) 0.69411(3) 0.47077(6) 0.0887(3) Uani 1 1 d . . .
O1 O 0.5006(4) 0.60724(18) 0.1520(4) 0.0460(8) Uani 1 1 d . . .
O2 O 0.7488(5) 0.5471(2) 0.1756(5) 0.0714(12) 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 0.041(3) 0.037(2) 0.042(3) 0.001(2) 0.008(2) 0.0043(19)
C2 0.052(3) 0.034(2) 0.029(2) -0.0027(19) 0.004(2) -0.008(2)
C3 0.075(4) 0.056(3) 0.034(3) -0.005(2) 0.008(3) -0.008(3)
C4 0.096(5) 0.069(4) 0.031(3) 0.005(3) -0.012(3) -0.020(3)
C5 0.068(4) 0.061(4) 0.056(4) 0.013(3) -0.025(3) -0.012(3)
C6 0.046(3) 0.056(3) 0.055(3) 0.009(3) -0.008(2) 0.004(2)
C7 0.042(3) 0.033(2) 0.038(3) 0.0045(19) -0.002(2) -0.0034(18)
C8 0.046(3) 0.052(3) 0.040(3) 0.002(2) 0.007(2) 0.007(2)
C9 0.039(3) 0.038(2) 0.040(3) 0.004(2) 0.004(2) 0.0020(19)
C10 0.046(3) 0.054(3) 0.045(3) 0.011(2) -0.002(2) 0.008(2)
C11 0.069(4) 0.070(4) 0.097(5) 0.029(4) -0.024(4) 0.001(3)
C12 0.068(4) 0.079(4) 0.059(4) 0.001(3) -0.018(3) 0.000(3)
I1 0.0870(4) 0.1025(4) 0.0830(4) 0.0047(3) 0.0365(3) 0.0459(3)
O1 0.048(2) 0.060(2) 0.0299(17) 0.0030(15) 0.0033(14) 0.0145(16)
O2 0.065(3) 0.100(3) 0.052(2) 0.005(2) 0.0191(19) 0.034(2)

_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 1.441(6) . ?
C1 C9 1.330(6) . ?
C1 I1 2.086(4) . ?
C2 C3 1.403(6) . ?
C2 C7 1.396(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.370(8) . ?
C4 H4 0.9300 . ?
C4 C5 1.371(9) . ?
C5 H5 0.9300 . ?
C5 C6 1.366(8) . ?
C6 H6 0.9300 . ?
C6 C7 1.380(7) . ?
C7 C8 1.463(6) . ?
C8 O1 1.373(6) . ?
C8 O2 1.202(6) . ?
C9 C10 1.485(7) . ?
C9 O1 1.382(5) . ?
C10 C11 1.320(8) . ?
C10 C12 1.482(8) . ?
C11 H11A 0.9300 . ?
C11 H11B 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 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 119.9(3) . . ?
C9 C1 C2 121.4(4) . . ?
C9 C1 I1 118.7(3) . . ?
C3 C2 C1 125.5(5) . . ?
C7 C2 C1 117.6(4) . . ?
C7 C2 C3 116.9(4) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 C2 120.4(5) . . ?
C4 C3 H3 119.8 . . ?
C3 C4 H4 119.3 . . ?
C5 C4 C3 121.5(5) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 120.2 . . ?
C6 C5 C4 119.7(5) . . ?
C6 C5 H5 120.2 . . ?
C5 C6 H6 120.2 . . ?
C5 C6 C7 119.6(5) . . ?
C7 C6 H6 120.2 . . ?
C2 C7 C8 120.5(4) . . ?
C6 C7 C2 122.0(4) . . ?
C6 C7 C8 117.4(4) . . ?
O1 C8 C7 116.9(4) . . ?
O2 C8 C7 126.5(5) . . ?
O2 C8 O1 116.7(4) . . ?
C1 C9 C10 129.9(4) . . ?
C1 C9 O1 121.0(4) . . ?
O1 C9 C10 109.1(4) . . ?
C11 C10 C9 118.7(5) . . ?
C11 C10 C12 125.0(5) . . ?
C12 C10 C9 116.3(4) . . ?
C10 C11 H11A 120.0 . . ?
C10 C11 H11B 120.0 . . ?
H11A C11 H11B 120.0 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C8 O1 C9 122.6(3) . . ?

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
C1 C2 C3 C4 -179.6(5) . . . . ?
C1 C2 C7 C6 179.9(4) . . . . ?
C1 C2 C7 C8 -0.5(6) . . . . ?
C1 C9 C10 C11 78.0(7) . . . . ?
C1 C9 C10 C12 -103.0(6) . . . . ?
C1 C9 O1 C8 -2.4(7) . . . . ?
C2 C1 C9 C10 -179.6(5) . . . . ?
C2 C1 C9 O1 1.9(7) . . . . ?
C2 C3 C4 C5 0.0(8) . . . . ?
C2 C7 C8 O1 0.1(7) . . . . ?
C2 C7 C8 O2 179.0(5) . . . . ?
C3 C2 C7 C6 0.6(7) . . . . ?
C3 C2 C7 C8 -179.8(4) . . . . ?
C3 C4 C5 C6 0.0(9) . . . . ?
C4 C5 C6 C7 0.3(8) . . . . ?
C5 C6 C7 C2 -0.6(7) . . . . ?
C5 C6 C7 C8 179.8(5) . . . . ?
C6 C7 C8 O1 179.7(4) . . . . ?
C6 C7 C8 O2 -1.4(8) . . . . ?
C7 C2 C3 C4 -0.3(7) . . . . ?
C7 C8 O1 C9 1.3(6) . . . . ?
C9 C1 C2 C3 178.8(5) . . . . ?
C9 C1 C2 C7 -0.5(6) . . . . ?
C10 C9 O1 C8 178.9(4) . . . . ?
I1 C1 C2 C3 -1.9(6) . . . . ?
I1 C1 C2 C7 178.8(3) . . . . ?
I1 C1 C9 C10 1.0(7) . . . . ?
I1 C1 C9 O1 -177.4(3) . . . . ?
O1 C9 C10 C11 -103.4(6) . . . . ?
O1 C9 C10 C12 75.7(6) . . . . ?
O2 C8 O1 C9 -177.7(5) . . . . ?