# Electronic Supplementary Material (ESI) for Chemical Communications
# This journal is © The Royal Society of Chemistry 2013

#######################################################################
#
#                 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
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# 
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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.
#
data_SC483c
#TrackingRef 'BAlcaide_SC483c.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H14 I N O'
_chemical_formula_weight         351.17

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

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)

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

_cell_length_a                   6.2989(9)
_cell_length_b                   11.2618(16)
_cell_length_c                   9.7942(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.974(2)
_cell_angle_gamma                90.00
_cell_volume                     674.21(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3345
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      25.17

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.730
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             344
_exptl_absorpt_coefficient_mu    2.362
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5158
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_sigmaI/netI    0.0325
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.14
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2303
_reflns_number_gt                2140
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0464P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.02(3)
_refine_ls_number_reflns         2303
_refine_ls_number_parameters     163
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0313
_refine_ls_R_factor_gt           0.0284
_refine_ls_wR_factor_ref         0.0721
_refine_ls_wR_factor_gt          0.0702
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_restrained_S_all      0.997
_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
C3 C 1.1052(8) 0.5357(4) 0.8935(5) 0.0467(10) Uani 1 1 d . . .
C2 C 1.3004(8) 0.6016(4) 0.9166(5) 0.0490(11) Uani 1 1 d . . .
C1 C 1.3095(8) 0.6980(4) 0.8291(5) 0.0511(11) Uani 1 1 d . . .
H1 H 1.4366 0.7431 0.8424 0.061 Uiso 1 1 calc R . .
C9A C 1.1283(8) 0.7266(4) 0.7222(5) 0.0467(10) Uani 1 1 d . . .
C8A C 0.8914(8) 0.8059(4) 0.5351(5) 0.0486(11) Uani 1 1 d . . .
C8 C 0.7988(9) 0.8711(6) 0.4160(5) 0.0593(14) Uani 1 1 d . . .
H8 H 0.8731 0.9343 0.3876 0.071 Uiso 1 1 calc R . .
C7 C 0.5909(10) 0.8388(5) 0.3402(6) 0.0661(15) Uani 1 1 d . . .
H7 H 0.5250 0.8806 0.2592 0.079 Uiso 1 1 calc R . .
C6 C 0.4794(9) 0.7447(5) 0.3837(6) 0.0582(13) Uani 1 1 d . . .
C5 C 0.5699(7) 0.6797(5) 0.5014(5) 0.0516(12) Uani 1 1 d . . .
H5 H 0.4937 0.6173 0.5297 0.062 Uiso 1 1 calc R . .
C4B C 0.7848(8) 0.7105(4) 0.5797(5) 0.0458(10) Uani 1 1 d . . .
C4A C 0.9300(9) 0.6599(4) 0.6990(6) 0.0457(13) Uani 1 1 d . . .
C4 C 0.9231(8) 0.5620(4) 0.7888(5) 0.0446(10) Uani 1 1 d . . .
H4 H 0.7971 0.5162 0.7770 0.053 Uiso 1 1 calc R . .
C11 C 0.1698(13) 0.6291(6) 0.3323(6) 0.0628(19) Uani 1 1 d . . .
H11A H 0.0278 0.6221 0.2691 0.094 Uiso 1 1 calc R . .
H11B H 0.1541 0.6364 0.4270 0.094 Uiso 1 1 calc R . .
H11C H 0.2546 0.5597 0.3247 0.094 Uiso 1 1 calc R . .
C12 C 1.2591(10) 0.9073(5) 0.6173(6) 0.0622(15) Uani 1 1 d . . .
H12A H 1.3904 0.8951 0.6896 0.093 Uiso 1 1 calc R . .
H12B H 1.1979 0.9834 0.6301 0.093 Uiso 1 1 calc R . .
H12C H 1.2929 0.9047 0.5268 0.093 Uiso 1 1 calc R . .
C10 C 1.5000(11) 0.5707(6) 1.0302(6) 0.0685(15) Uani 1 1 d . . .
H10A H 1.6141 0.6269 1.0291 0.103 Uiso 1 1 calc R . .
H10B H 1.5487 0.4924 1.0139 0.103 Uiso 1 1 calc R . .
H10C H 1.4644 0.5731 1.1201 0.103 Uiso 1 1 calc R . .
I1 I 1.07935(4) 0.38667(3) 1.01975(3) 0.06315(13) Uani 1 1 d . . .
N9 N 1.1023(7) 0.8148(3) 0.6252(4) 0.0527(10) Uani 1 1 d . . .
O1 O 0.2735(7) 0.7276(5) 0.2981(4) 0.0811(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
C3 0.061(3) 0.043(2) 0.040(2) 0.0034(18) 0.019(2) 0.002(2)
C2 0.052(3) 0.053(2) 0.042(2) -0.004(2) 0.011(2) 0.004(2)
C1 0.052(3) 0.047(2) 0.058(3) -0.010(2) 0.021(2) -0.008(2)
C9A 0.058(3) 0.038(2) 0.046(2) -0.0036(18) 0.018(2) -0.003(2)
C8A 0.055(3) 0.044(2) 0.049(3) -0.003(2) 0.018(2) 0.003(2)
C8 0.074(3) 0.047(4) 0.062(3) 0.009(3) 0.026(2) 0.006(3)
C7 0.075(4) 0.067(3) 0.060(3) 0.017(2) 0.024(3) 0.021(3)
C6 0.055(3) 0.064(3) 0.056(3) 0.002(2) 0.015(3) 0.011(2)
C5 0.051(3) 0.048(2) 0.057(3) 0.004(2) 0.017(2) 0.0073(19)
C4B 0.054(3) 0.038(2) 0.050(3) -0.0005(19) 0.024(2) 0.0029(19)
C4A 0.057(4) 0.035(2) 0.048(3) -0.0027(19) 0.017(2) 0.001(2)
C4 0.050(3) 0.044(2) 0.041(2) 0.0042(17) 0.015(2) -0.0019(19)
C11 0.085(5) 0.058(3) 0.044(3) -0.007(3) 0.012(3) 0.011(3)
C12 0.078(3) 0.040(4) 0.073(3) -0.001(2) 0.026(3) -0.014(3)
C10 0.052(3) 0.084(4) 0.065(3) 0.011(3) 0.004(3) 0.002(3)
I1 0.0723(2) 0.05856(17) 0.05577(18) 0.01577(19) 0.00991(13) -0.0002(2)
N9 0.064(3) 0.0391(19) 0.057(2) 0.0020(17) 0.020(2) -0.0081(19)
O1 0.061(3) 0.101(3) 0.070(3) 0.023(2) -0.005(2) 0.013(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
C3 C4 1.374(7) . ?
C3 C2 1.407(7) . ?
C3 I1 2.114(4) . ?
C2 C1 1.393(7) . ?
C2 C10 1.504(8) . ?
C1 C9A 1.388(7) . ?
C1 H1 0.9300 . ?
C9A N9 1.357(6) . ?
C9A C4A 1.428(7) . ?
C8A C8 1.382(8) . ?
C8A C4B 1.392(7) . ?
C8A N9 1.410(7) . ?
C8 C7 1.389(8) . ?
C8 H8 0.9300 . ?
C7 C6 1.393(8) . ?
C7 H7 0.9300 . ?
C6 C5 1.369(7) . ?
C6 O1 1.377(7) . ?
C5 C4B 1.428(7) . ?
C5 H5 0.9300 . ?
C4B C4A 1.418(7) . ?
C4A C4 1.417(6) . ?
C4 H4 0.9300 . ?
C11 O1 1.369(8) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 N9 1.451(7) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 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
C4 C3 C2 123.1(4) . . ?
C4 C3 I1 116.1(3) . . ?
C2 C3 I1 120.8(3) . . ?
C1 C2 C3 118.4(4) . . ?
C1 C2 C10 118.9(5) . . ?
C3 C2 C10 122.6(5) . . ?
C2 C1 C9A 119.8(4) . . ?
C2 C1 H1 120.1 . . ?
C9A C1 H1 120.1 . . ?
N9 C9A C1 129.5(4) . . ?
N9 C9A C4A 108.7(4) . . ?
C1 C9A C4A 121.8(4) . . ?
C8 C8A C4B 122.5(5) . . ?
C8 C8A N9 129.2(5) . . ?
C4B C8A N9 108.1(4) . . ?
C8A C8 C7 117.6(6) . . ?
C8A C8 H8 121.2 . . ?
C7 C8 H8 121.2 . . ?
C6 C7 C8 121.1(5) . . ?
C6 C7 H7 119.5 . . ?
C8 C7 H7 119.5 . . ?
C5 C6 O1 125.2(5) . . ?
C5 C6 C7 121.7(5) . . ?
O1 C6 C7 113.0(5) . . ?
C6 C5 C4B 118.1(5) . . ?
C6 C5 H5 121.0 . . ?
C4B C5 H5 121.0 . . ?
C8A C4B C4A 107.8(4) . . ?
C8A C4B C5 119.0(5) . . ?
C4A C4B C5 133.1(5) . . ?
C4B C4A C9A 106.5(4) . . ?
C4B C4A C4 135.6(5) . . ?
C9A C4A C4 117.8(5) . . ?
C3 C4 C4A 119.1(5) . . ?
C3 C4 H4 120.5 . . ?
C4A C4 H4 120.5 . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N9 C12 H12A 109.5 . . ?
N9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C2 C10 H10A 109.5 . . ?
C2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C9A N9 C8A 108.8(4) . . ?
C9A N9 C12 126.5(5) . . ?
C8A N9 C12 124.6(4) . . ?
C6 O1 C11 113.6(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
C4 C3 C2 C1 0.0(7) . . . . ?
I1 C3 C2 C1 179.1(3) . . . . ?
C4 C3 C2 C10 -179.0(5) . . . . ?
I1 C3 C2 C10 0.2(7) . . . . ?
C3 C2 C1 C9A -0.2(7) . . . . ?
C10 C2 C1 C9A 178.8(5) . . . . ?
C2 C1 C9A N9 -179.3(5) . . . . ?
C2 C1 C9A C4A 0.4(7) . . . . ?
C4B C8A C8 C7 0.4(8) . . . . ?
N9 C8A C8 C7 175.7(5) . . . . ?
C8A C8 C7 C6 0.5(8) . . . . ?
C8 C7 C6 C5 -0.6(8) . . . . ?
C8 C7 C6 O1 178.3(5) . . . . ?
O1 C6 C5 C4B -179.0(5) . . . . ?
C7 C6 C5 C4B -0.3(8) . . . . ?
C8 C8A C4B C4A 176.5(5) . . . . ?
N9 C8A C4B C4A 0.3(5) . . . . ?
C8 C8A C4B C5 -1.3(7) . . . . ?
N9 C8A C4B C5 -177.5(4) . . . . ?
C6 C5 C4B C8A 1.2(7) . . . . ?
C6 C5 C4B C4A -175.9(5) . . . . ?
C8A C4B C4A C9A -1.3(5) . . . . ?
C5 C4B C4A C9A 176.1(5) . . . . ?
C8A C4B C4A C4 -178.2(5) . . . . ?
C5 C4B C4A C4 -0.8(10) . . . . ?
N9 C9A C4A C4B 1.8(5) . . . . ?
C1 C9A C4A C4B -177.9(4) . . . . ?
N9 C9A C4A C4 179.4(4) . . . . ?
C1 C9A C4A C4 -0.4(7) . . . . ?
C2 C3 C4 C4A 0.0(7) . . . . ?
I1 C3 C4 C4A -179.2(3) . . . . ?
C4B C4A C4 C3 176.8(5) . . . . ?
C9A C4A C4 C3 0.2(6) . . . . ?
C1 C9A N9 C8A 178.0(5) . . . . ?
C4A C9A N9 C8A -1.6(5) . . . . ?
C1 C9A N9 C12 -4.6(8) . . . . ?
C4A C9A N9 C12 175.7(5) . . . . ?
C8 C8A N9 C9A -175.0(5) . . . . ?
C4B C8A N9 C9A 0.8(5) . . . . ?
C8 C8A N9 C12 7.5(8) . . . . ?
C4B C8A N9 C12 -176.6(4) . . . . ?
C5 C6 O1 C11 -6.6(8) . . . . ?
C7 C6 O1 C11 174.6(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.979
_refine_diff_density_max         0.535
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.073


#===================================================================END


_database_code_depnum_ccdc_archive 'CCDC 926119'