# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_150618g_0m
_database_code_depnum_ccdc_archive 'CCDC 1485477'
_audit_update_record             
;
2016-06-14 deposited with the CCDC.
2016-08-30 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H11 I N2 O'
_chemical_formula_weight         398.19

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

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   7.504(11)
_cell_length_b                   8.467(12)
_cell_length_c                   13.179(18)
_cell_angle_alpha                95.607(18)
_cell_angle_beta                 102.60(2)
_cell_angle_gamma                110.95(2)
_cell_volume                     748.8(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4995
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      29.91

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.766
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             388
_exptl_absorpt_coefficient_mu    2.141
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  0.5660
_exptl_absorpt_correction_T_max  0.9005
_exptl_absorpt_process_details   ?

_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_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10330
_diffrn_reflns_av_R_equivalents  0.0244
_diffrn_reflns_av_sigmaI/netI    0.0290
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.61
_diffrn_reflns_theta_max         29.00
_reflns_number_total             3963
_reflns_number_gt                3229
_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, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0625P)²+0.1752P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3963
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.1136
_refine_ls_wR_factor_gt          0.0994
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_restrained_S_all      1.141
_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 0.7614(5) 0.7023(5) 1.3320(3) 0.0573(8) Uani 1 1 d . . .
H1 H 0.7347 0.6017 1.3594 0.069 Uiso 1 1 calc R . .
C2 C 0.7861(6) 0.8526(5) 1.3940(3) 0.0620(9) Uani 1 1 d . . .
H2 H 0.7774 0.8534 1.4633 0.074 Uiso 1 1 calc R . .
C3 C 0.8247(5) 1.0056(5) 1.3534(3) 0.0609(9) Uani 1 1 d . . .
H3 H 0.8396 1.1063 1.3959 0.073 Uiso 1 1 calc R . .
C4 C 0.8404(5) 1.0075(5) 1.2517(3) 0.0541(7) Uani 1 1 d . . .
H4 H 0.8671 1.1096 1.2261 0.065 Uiso 1 1 calc R . .
C5 C 0.8161(4) 0.8536(4) 1.1851(2) 0.0445(6) Uani 1 1 d . . .
C6 C 0.7764(4) 0.6991(4) 1.2260(2) 0.0431(6) Uani 1 1 d . . .
C7 C 0.7522(4) 0.5466(4) 1.1592(2) 0.0446(6) Uani 1 1 d . . .
H7 H 0.7281 0.4456 1.1861 0.054 Uiso 1 1 calc R . .
C8 C 0.7631(4) 0.5428(4) 1.0555(2) 0.0409(5) Uani 1 1 d . . .
C9 C 0.8063(5) 0.6998(4) 1.0159(2) 0.0492(6) Uani 1 1 d . . .
H9 H 0.8165 0.7004 0.9469 0.059 Uiso 1 1 calc R . .
C10 C 0.8328(5) 0.8499(4) 1.0792(3) 0.0534(7) Uani 1 1 d . . .
H10 H 0.8622 0.9511 1.0525 0.064 Uiso 1 1 calc R . .
C11 C 0.7262(4) 0.3689(4) 0.9941(2) 0.0448(6) Uani 1 1 d . . .
C12 C 0.7257(4) 0.3432(3) 0.8813(2) 0.0391(5) Uani 1 1 d . . .
C13 C 0.7565(4) 0.3817(4) 0.7262(2) 0.0417(5) Uani 1 1 d . . .
C14 C 0.7090(4) 0.2051(4) 0.7226(2) 0.0397(5) Uani 1 1 d . . .
C15 C 0.6824(5) 0.0638(4) 0.6457(3) 0.0492(6) Uani 1 1 d . . .
H15 H 0.6956 0.0791 0.5784 0.059 Uiso 1 1 calc R . .
C16 C 0.6373(5) -0.0948(4) 0.6718(3) 0.0571(8) Uani 1 1 d . . .
H16 H 0.6207 -0.1888 0.6225 0.069 Uiso 1 1 calc R . .
C17 C 0.6155(5) -0.1162(4) 0.7744(3) 0.0576(8) Uani 1 1 d . . .
H17 H 0.5849 -0.2251 0.7915 0.069 Uiso 1 1 calc R . .
C18 C 0.6381(5) 0.0179(4) 0.8481(3) 0.0516(7) Uani 1 1 d . . .
H18 H 0.6198 0.0007 0.9144 0.062 Uiso 1 1 calc R . .
I1 I 0.80613(4) 0.50135(3) 0.598621(16) 0.06625(12) Uani 1 1 d . . .
N1 N 0.7652(3) 0.4631(3) 0.82056(19) 0.0416(5) Uani 1 1 d . . .
N2 N 0.6889(3) 0.1815(3) 0.82357(18) 0.0399(5) Uani 1 1 d . . .
O1 O 0.6967(5) 0.2441(3) 1.0383(2) 0.0689(7) Uani 1 1 d . . .


_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 1.372(6) . ?
C1 C6 1.425(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.409(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.428(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.421(5) . ?
C5 C10 1.426(5) . ?
C6 C7 1.419(5) . ?
C7 C8 1.385(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.430(4) . ?
C8 C11 1.509(5) . ?
C9 C10 1.374(5) . ?
C9 H9 0.9300 . ?
C10 H10 0.9300 . ?
C11 O1 1.230(4) . ?
C11 C12 1.481(4) . ?
C12 N1 1.344(4) . ?
C12 N2 1.402(4) . ?
C13 N1 1.338(4) . ?
C13 C14 1.401(4) . ?
C13 I1 2.080(3) . ?
C14 N2 1.396(4) . ?
C14 C15 1.415(4) . ?
C15 C16 1.361(5) . ?
C15 H15 0.9300 . ?
C16 C17 1.418(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.355(5) . ?
C17 H17 0.9300 . ?
C18 N2 1.390(4) . ?
C18 H18 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 C6 120.5(3) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C1 C2 C3 120.5(3) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 120.7(3) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.4(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
C6 C5 C10 118.7(3) . . ?
C6 C5 C4 118.9(3) . . ?
C10 C5 C4 122.3(3) . . ?
C7 C6 C5 118.6(3) . . ?
C7 C6 C1 122.3(3) . . ?
C5 C6 C1 119.0(3) . . ?
C8 C7 C6 122.3(3) . . ?
C8 C7 H7 118.8 . . ?
C6 C7 H7 118.8 . . ?
C7 C8 C9 118.5(3) . . ?
C7 C8 C11 115.6(3) . . ?
C9 C8 C11 126.0(3) . . ?
C10 C9 C8 120.4(3) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C5 121.4(3) . . ?
C9 C10 H10 119.3 . . ?
C5 C10 H10 119.3 . . ?
O1 C11 C12 118.4(3) . . ?
O1 C11 C8 119.8(3) . . ?
C12 C11 C8 121.8(2) . . ?
N1 C12 N2 110.1(2) . . ?
N1 C12 C11 127.8(3) . . ?
N2 C12 C11 122.0(2) . . ?
N1 C13 C14 112.1(2) . . ?
N1 C13 I1 124.4(2) . . ?
C14 C13 I1 123.5(2) . . ?
N2 C14 C13 104.2(2) . . ?
N2 C14 C15 120.3(3) . . ?
C13 C14 C15 135.5(3) . . ?
C16 C15 C14 118.9(3) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C15 C16 C17 119.8(3) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C18 C17 C16 121.7(3) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 N2 119.2(3) . . ?
C17 C18 H18 120.4 . . ?
N2 C18 H18 120.4 . . ?
C13 N1 C12 106.6(3) . . ?
C18 N2 C14 120.0(3) . . ?
C18 N2 C12 133.0(3) . . ?
C14 N2 C12 107.0(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.7(5) . . . . ?
C1 C2 C3 C4 -0.7(6) . . . . ?
C2 C3 C4 C5 0.6(5) . . . . ?
C3 C4 C5 C6 -0.3(5) . . . . ?
C3 C4 C5 C10 -179.5(3) . . . . ?
C10 C5 C6 C7 -0.9(4) . . . . ?
C4 C5 C6 C7 179.9(3) . . . . ?
C10 C5 C6 C1 179.4(3) . . . . ?
C4 C5 C6 C1 0.2(4) . . . . ?
C2 C1 C6 C7 179.9(3) . . . . ?
C2 C1 C6 C5 -0.4(5) . . . . ?
C5 C6 C7 C8 -0.9(4) . . . . ?
C1 C6 C7 C8 178.8(3) . . . . ?
C6 C7 C8 C9 1.9(4) . . . . ?
C6 C7 C8 C11 -177.8(3) . . . . ?
C7 C8 C9 C10 -1.1(5) . . . . ?
C11 C8 C9 C10 178.6(3) . . . . ?
C8 C9 C10 C5 -0.7(5) . . . . ?
C6 C5 C10 C9 1.7(5) . . . . ?
C4 C5 C10 C9 -179.1(3) . . . . ?
C7 C8 C11 O1 -2.7(4) . . . . ?
C9 C8 C11 O1 177.7(3) . . . . ?
C7 C8 C11 C12 177.8(2) . . . . ?
C9 C8 C11 C12 -1.9(4) . . . . ?
O1 C11 C12 N1 -176.0(3) . . . . ?
C8 C11 C12 N1 3.6(4) . . . . ?
O1 C11 C12 N2 1.3(4) . . . . ?
C8 C11 C12 N2 -179.1(2) . . . . ?
N1 C13 C14 N2 -0.2(3) . . . . ?
I1 C13 C14 N2 -179.96(18) . . . . ?
N1 C13 C14 C15 -179.6(3) . . . . ?
I1 C13 C14 C15 0.6(5) . . . . ?
N2 C14 C15 C16 0.0(4) . . . . ?
C13 C14 C15 C16 179.3(3) . . . . ?
C14 C15 C16 C17 0.7(5) . . . . ?
C15 C16 C17 C18 0.2(5) . . . . ?
C16 C17 C18 N2 -1.7(5) . . . . ?
C14 C13 N1 C12 0.5(3) . . . . ?
I1 C13 N1 C12 -179.70(19) . . . . ?
N2 C12 N1 C13 -0.7(3) . . . . ?
C11 C12 N1 C13 176.9(3) . . . . ?
C17 C18 N2 C14 2.3(4) . . . . ?
C17 C18 N2 C12 -178.7(3) . . . . ?
C13 C14 N2 C18 179.0(3) . . . . ?
C15 C14 N2 C18 -1.5(4) . . . . ?
C13 C14 N2 C12 -0.2(3) . . . . ?
C15 C14 N2 C12 179.3(3) . . . . ?
N1 C12 N2 C18 -178.5(3) . . . . ?
C11 C12 N2 C18 3.7(5) . . . . ?
N1 C12 N2 C14 0.5(3) . . . . ?
C11 C12 N2 C14 -177.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        29.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         1.293
_refine_diff_density_min         -0.667
_refine_diff_density_rms         0.112
