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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
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#  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.
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data_mat

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H11 I O3'
_chemical_formula_weight         294.08

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'

_symmetry_space_group_name_H-M   'P -1'
_symmetry_cell_setting           triclinic

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

_cell_length_a                   7.6999(5)
_cell_length_b                   8.0494(6)
_cell_length_c                   9.5070(7)
_cell_angle_alpha                104.034(6)
_cell_angle_beta                 112.572(5)
_cell_angle_gamma                100.066(6)
_cell_volume                     503.72(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2677
_cell_measurement_theta_min      2.9939
_cell_measurement_theta_max      28.9420

_exptl_crystal_description       PRISM
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.939
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             284
_exptl_absorpt_coefficient_mu    3.152
_exptl_absorpt_correction_T_min  0.56619
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET)
(compiled Apr 21 2008,18:23:10)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.3280
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4135
_diffrn_reflns_av_R_equivalents  0.0185
_diffrn_reflns_av_sigmaI/netI    0.0248
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.00
_diffrn_reflns_theta_max         24.99
_reflns_number_total             1769
_reflns_number_gt                1500
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET)
(compiled Apr 21 2008,18:23:10)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET)
(compiled Apr 21 2008,18:23:10)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET)
(compiled Apr 21 2008,18:23:10)
;
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 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)+(0.0162P)²+4.4227P] 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     SHELXL
_refine_ls_extinction_coef       0.0091(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1769
_refine_ls_number_parameters     120
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0593
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.1076
_refine_ls_wR_factor_gt          0.1039
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_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
I I 0.68490(9) 0.37847(10) 0.42235(7) 0.0695(3) Uani 1 1 d . . .
O2 O 0.9658(6) 0.4721(6) 0.8224(5) 0.0332(10) Uani 1 1 d . . .
O3 O 1.2841(7) 0.6221(6) 0.9647(6) 0.0438(12) Uani 1 1 d . . .
O4 O 1.3317(6) 0.2994(7) 0.7829(5) 0.0385(11) Uani 1 1 d . . .
H4 H 1.4382 0.3252 0.8621 0.058 Uiso 1 1 calc R . .
C5 C 0.9810(9) 0.1880(8) 0.6905(7) 0.0287(14) Uani 1 1 d . . .
H5 H 0.9815 0.2050 0.5920 0.034 Uiso 1 1 calc R . .
C6 C 1.1810(8) 0.2946(8) 0.8328(7) 0.0261(13) Uani 1 1 d . . .
C7 C 0.9251(10) -0.0084(9) 0.6636(9) 0.0416(17) Uani 1 1 d . . .
H7 H 0.8119 -0.0837 0.5716 0.050 Uiso 1 1 calc R . .
C8 C 1.2196(10) 0.2222(9) 0.9733(8) 0.0365(15) Uani 1 1 d . . .
H8A H 1.1227 0.2361 1.0133 0.044 Uiso 1 1 calc R . .
H8B H 1.3491 0.2908 1.0611 0.044 Uiso 1 1 calc R . .
C9 C 1.1582(9) 0.4811(9) 0.8833(7) 0.0314(14) Uani 1 1 d . . .
C10 C 0.8446(9) 0.2849(9) 0.7351(8) 0.0318(14) Uani 1 1 d . . .
H10 H 0.8125 0.2378 0.8108 0.038 Uiso 1 1 calc R . .
C11 C 1.2088(12) 0.0253(10) 0.9191(9) 0.0491(19) Uani 1 1 d . . .
H11A H 1.3248 0.0146 0.9045 0.059 Uiso 1 1 calc R . .
H11B H 1.2081 -0.0236 1.0027 0.059 Uiso 1 1 calc R . .
C12 C 1.0305(11) -0.0797(10) 0.7659(10) 0.0486(19) Uani 1 1 d . . .
H12 H 0.9895 -0.2036 0.7394 0.058 Uiso 1 1 calc R . .
C13 C 0.6552(10) 0.2768(10) 0.6011(9) 0.0440(18) Uani 1 1 d . . .
H13A H 0.5863 0.3436 0.6487 0.053 Uiso 1 1 calc R . .
H13B H 0.5732 0.1528 0.5479 0.053 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
I 0.0572(4) 0.1209(7) 0.0470(4) 0.0449(4) 0.0212(3) 0.0470(4)
O2 0.034(2) 0.028(2) 0.034(2) 0.007(2) 0.012(2) 0.013(2)
O3 0.040(3) 0.033(3) 0.043(3) 0.007(2) 0.010(2) 0.005(2)
O4 0.029(2) 0.056(3) 0.035(2) 0.016(2) 0.018(2) 0.015(2)
C5 0.027(3) 0.033(4) 0.026(3) 0.008(3) 0.011(3) 0.012(3)
C6 0.025(3) 0.026(3) 0.025(3) 0.008(3) 0.011(3) 0.007(3)
C7 0.037(4) 0.034(4) 0.047(4) 0.001(3) 0.021(3) 0.009(3)
C8 0.040(4) 0.044(4) 0.028(3) 0.016(3) 0.012(3) 0.019(3)
C9 0.034(3) 0.038(4) 0.026(3) 0.016(3) 0.013(3) 0.013(3)
C10 0.031(3) 0.033(4) 0.034(3) 0.012(3) 0.015(3) 0.013(3)
C11 0.064(5) 0.048(5) 0.053(5) 0.030(4) 0.029(4) 0.031(4)
C12 0.053(5) 0.030(4) 0.066(5) 0.012(4) 0.031(4) 0.015(4)
C13 0.028(3) 0.046(4) 0.053(4) 0.017(4) 0.012(3) 0.012(3)

_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
I C13 2.125(8) . ?
O2 C9 1.349(7) . ?
O2 C10 1.462(8) . ?
O3 C9 1.200(8) . ?
O4 C6 1.410(7) . ?
O4 H4 0.8200 . ?
C5 C6 1.521(8) . ?
C5 C10 1.535(8) . ?
C5 C7 1.494(9) . ?
C5 H5 0.9800 . ?
C6 C8 1.531(8) . ?
C6 C9 1.524(9) . ?
C7 C12 1.326(10) . ?
C7 H7 0.9300 . ?
C8 C11 1.519(10) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C10 C13 1.502(9) . ?
C10 H10 0.9800 . ?
C11 C12 1.478(11) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 H12 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?

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
C9 O2 C10 109.7(5) . . ?
C6 O4 H4 109.5 . . ?
C6 C5 C10 101.8(5) . . ?
C6 C5 C7 114.1(5) . . ?
C10 C5 C7 114.3(5) . . ?
C6 C5 H5 108.8 . . ?
C10 C5 H5 108.8 . . ?
C7 C5 H5 108.8 . . ?
O4 C6 C5 110.7(5) . . ?
O4 C6 C8 112.2(5) . . ?
C5 C6 C8 111.3(5) . . ?
O4 C6 C9 110.6(5) . . ?
C5 C6 C9 102.6(5) . . ?
C8 C6 C9 109.2(5) . . ?
C12 C7 C5 122.6(7) . . ?
C12 C7 H7 118.7 . . ?
C5 C7 H7 118.7 . . ?
C6 C8 C11 110.8(5) . . ?
C6 C8 H8A 109.5 . . ?
C11 C8 H8A 109.5 . . ?
C6 C8 H8B 109.5 . . ?
C11 C8 H8B 109.5 . . ?
H8A C8 H8B 108.1 . . ?
O3 C9 O2 120.9(6) . . ?
O3 C9 C6 128.7(6) . . ?
O2 C9 C6 110.3(5) . . ?
O2 C10 C13 109.2(5) . . ?
O2 C10 C5 104.7(5) . . ?
C13 C10 C5 118.5(6) . . ?
O2 C10 H10 108.0 . . ?
C13 C10 H10 108.0 . . ?
C5 C10 H10 108.0 . . ?
C12 C11 C8 111.6(6) . . ?
C12 C11 H11A 109.3 . . ?
C8 C11 H11A 109.3 . . ?
C12 C11 H11B 109.3 . . ?
C8 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C7 C12 C11 124.2(7) . . ?
C7 C12 H12 117.9 . . ?
C11 C12 H12 117.9 . . ?
C10 C13 I 115.5(5) . . ?
C10 C13 H13A 108.4 . . ?
I C13 H13A 108.4 . . ?
C10 C13 H13B 108.4 . . ?
I C13 H13B 108.4 . . ?
H13A C13 H13B 107.5 . . ?

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
C10 C5 C6 O4 -147.8(5) . . . . ?
C7 C5 C6 O4 88.6(6) . . . . ?
C10 C5 C6 C8 86.7(6) . . . . ?
C7 C5 C6 C8 -36.9(7) . . . . ?
C10 C5 C6 C9 -29.9(6) . . . . ?
C7 C5 C6 C9 -153.5(5) . . . . ?
C6 C5 C7 C12 7.2(9) . . . . ?
C10 C5 C7 C12 -109.3(8) . . . . ?
O4 C6 C8 C11 -66.7(7) . . . . ?
C5 C6 C8 C11 57.9(7) . . . . ?
C9 C6 C8 C11 170.4(6) . . . . ?
C10 O2 C9 O3 -177.4(6) . . . . ?
C10 O2 C9 C6 2.7(6) . . . . ?
O4 C6 C9 O3 -43.8(8) . . . . ?
C5 C6 C9 O3 -161.8(6) . . . . ?
C8 C6 C9 O3 80.1(8) . . . . ?
O4 C6 C9 O2 136.2(5) . . . . ?
C5 C6 C9 O2 18.2(6) . . . . ?
C8 C6 C9 O2 -100.0(6) . . . . ?
C9 O2 C10 C13 -150.3(5) . . . . ?
C9 O2 C10 C5 -22.5(6) . . . . ?
C6 C5 C10 O2 32.3(6) . . . . ?
C7 C5 C10 O2 155.8(5) . . . . ?
C6 C5 C10 C13 154.3(6) . . . . ?
C7 C5 C10 C13 -82.2(8) . . . . ?
C6 C8 C11 C12 -48.0(8) . . . . ?
C5 C7 C12 C11 2.3(12) . . . . ?
C8 C11 C12 C7 18.8(11) . . . . ?
O2 C10 C13 I 61.2(6) . . . . ?
C5 C10 C13 I -58.4(7) . . . . ?

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
O4 H4 O3 0.82 2.03 2.841(7) 172.1 2_867

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         2.436
_refine_diff_density_min         -2.034
_refine_diff_density_rms         0.120

_iucr_refine_instructions_details 
;
TITL    MAT in P-1
CELL 0.71073   7.6999   8.0494   9.5070 104.0335 112.5715 100.0660
ZERR    2.00   0.0005   0.0006   0.0007   0.0064   0.0063   0.0056
LATT  1
SFAC    C   H   O   I
UNIT    18  22   6   2
MERG    2
OMIT -3 50
L.S.    8
BOND $H
CONF
EQIV $1 -x+3, -y+1, -z+2
HTAB O4 O3_$1
REM HFIX 13 C5 C10
REM HFIX 23 C8 C11 C13
REM HFIX 43 C7 C12
REM HFIX 147 O4
FMAP    2
PLAN    25
ACTA
WGHT    0.016200    4.422700
EXTI    0.009115
FVAR       8.43142
I     4    0.684900    0.378468    0.422350    11.00000    0.05724    0.12092 =
         0.04696    0.04489    0.02123    0.04699
O2    3    0.965772    0.472118    0.822401    11.00000    0.03394    0.02791 =
         0.03407    0.00739    0.01186    0.01313
O3    3    1.284099    0.622054    0.964663    11.00000    0.03977    0.03323 =
         0.04307    0.00659    0.00977    0.00467
O4    3    1.331706    0.299400    0.782922    11.00000    0.02904    0.05557 =
         0.03543    0.01607    0.01765    0.01492
AFIX 147
H4    2    1.438162    0.325202    0.862064    11.00000   -1.50000
AFIX   0
C5    1    0.980989    0.188038    0.690518    11.00000    0.02706    0.03265 =
         0.02583    0.00827    0.01090    0.01186
AFIX  13
H5    2    0.981465    0.204976    0.591991    11.00000   -1.20000
AFIX   0
C6    1    1.181001    0.294611    0.832845    11.00000    0.02545    0.02646 =
         0.02513    0.00817    0.01077    0.00672
C7    1    0.925063   -0.008433    0.663627    11.00000    0.03748    0.03369 =
         0.04724    0.00067    0.02107    0.00941
AFIX  43
H7    2    0.811920   -0.083717    0.571593    11.00000   -1.20000
AFIX   0
C8    1    1.219649    0.222156    0.973290    11.00000    0.04004    0.04360 =
         0.02824    0.01640    0.01228    0.01880
AFIX  23
H8A   2    1.122705    0.236051    1.013298    11.00000   -1.20000
H8B   2    1.349086    0.290816    1.061142    11.00000   -1.20000
AFIX   0
C9    1    1.158186    0.481113    0.883336    11.00000    0.03370    0.03802 =
         0.02588    0.01586    0.01294    0.01265
C10   1    0.844622    0.284934    0.735067    11.00000    0.03089    0.03344 =
         0.03357    0.01234    0.01467    0.01347
AFIX  13
H10   2    0.812550    0.237778    0.810839    11.00000   -1.20000
AFIX   0
C11   1    1.208806    0.025269    0.919072    11.00000    0.06367    0.04779 =
         0.05269    0.03046    0.02854    0.03120
AFIX  23
H11A  2    1.324842    0.014643    0.904487    11.00000   -1.20000
H11B  2    1.208084   -0.023556    1.002709    11.00000   -1.20000
AFIX   0
C12   1    1.030451   -0.079675    0.765863    11.00000    0.05252    0.03038 =
         0.06634    0.01246    0.03134    0.01497
AFIX  43
H12   2    0.989469   -0.203572    0.739427    11.00000   -1.20000
AFIX   0
C13   1    0.655156    0.276820    0.601086    11.00000    0.02837    0.04592 =
         0.05257    0.01718    0.01228    0.01186
AFIX  23
H13A  2    0.586342    0.343624    0.648741    11.00000   -1.20000
H13B  2    0.573209    0.152764    0.547919    11.00000   -1.20000
 
HKLF      4
 
REM     MAT in P-1
REM R1 =  0.0501 for   1500 Fo > 4sig(Fo)  and  0.0593 for all   1769 data
REM    120 parameters refined using      0 restraints
 
END
;
_database_code_depnum_ccdc_archive 'CCDC 992966'
