# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2017

####################################################################### 
# 
# 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_2_a
_database_code_depnum_ccdc_archive 'CCDC 1497199'
_audit_update_record             
;
2016-08-02 deposited with the CCDC.
2017-02-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H11 I N2 O2'
_chemical_formula_weight         342.13

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'
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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Cmca

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

_cell_length_a                   6.9379(19)
_cell_length_b                   19.798(6)
_cell_length_c                   17.773(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2441.2(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5632
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      27.55

_exptl_crystal_description       block
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.862
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1328
_exptl_absorpt_coefficient_mu    2.615
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5387
_exptl_absorpt_correction_T_max  0.5970
_exptl_absorpt_process_details   sadabs

_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_reflns_number            9842
_diffrn_reflns_av_R_equivalents  0.0566
_diffrn_reflns_av_sigmaI/netI    0.0319
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.36
_diffrn_reflns_theta_max         27.60
_reflns_number_total             1524
_reflns_number_gt                1364
_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-2014 (Sheldrick 2014)'
_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)+(0.0375P)²+7.1092P] 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     SHELXL
_refine_ls_extinction_coef       0.0068(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1524
_refine_ls_number_parameters     106
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_ref         0.0901
_refine_ls_wR_factor_gt          0.0866
_refine_ls_goodness_of_fit_ref   1.130
_refine_ls_restrained_S_all      1.130
_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 0.0000 0.306249(17) 0.516246(17) 0.0466(2) Uani 1 2 d S . .
O1 O 0.0000 0.43877(17) 0.4240(2) 0.0533(11) Uani 1 2 d S . .
O2 O 0.0000 0.47382(19) 0.1554(2) 0.0651(14) Uani 1 2 d S . .
N1 N 0.0000 0.35973(19) 0.1654(2) 0.0409(10) Uani 1 2 d S . .
H1A H 0.0000 0.3204 0.1392 0.049 Uiso 1 2 d SR . .
N2 N 0.0000 0.2324(2) 0.2151(2) 0.0407(10) Uani 1 2 d S . .
C1 C 0.0000 0.1691(2) 0.2377(3) 0.0458(13) Uani 1 2 d S . .
H1 H 0.0000 0.1351 0.2016 0.055 Uiso 1 2 calc SR . .
C2 C 0.0000 0.1503(3) 0.3139(3) 0.0458(13) Uani 1 2 d S . .
H2 H 0.0000 0.1049 0.3273 0.055 Uiso 1 2 calc SR . .
C3 C 0.0000 0.1985(2) 0.3675(3) 0.0414(12) Uani 1 2 d S . .
H3 H 0.0000 0.1863 0.4180 0.050 Uiso 1 2 calc SR . .
C4 C 0.0000 0.2676(2) 0.3470(3) 0.0340(10) Uani 1 2 d S . .
C5 C 0.0000 0.3224(2) 0.3996(3) 0.0374(11) Uani 1 2 d S . .
C6 C 0.0000 0.3881(2) 0.3720(3) 0.0388(11) Uani 1 2 d S . .
C7 C 0.0000 0.4017(2) 0.2944(3) 0.0383(11) Uani 1 2 d S . .
H7 H 0.0000 0.4462 0.2777 0.046 Uiso 1 2 calc SR . .
C8 C 0.0000 0.3502(2) 0.2434(2) 0.0335(10) Uani 1 2 d S . .
C9 C 0.0000 0.2816(2) 0.2689(3) 0.0325(9) Uani 1 2 d S . .
C10 C 0.0000 0.4182(3) 0.1260(3) 0.0437(12) Uani 1 2 d S . .
C11 C 0.0000 0.4091(3) 0.0420(3) 0.0588(17) Uani 1 2 d S . .
H11A H 0.0698 0.4455 0.0190 0.088 Uiso 0.50 1 calc PR . .
H11B H -0.1303 0.4090 0.0239 0.088 Uiso 0.50 1 calc PR . .
H11C H 0.0605 0.3670 0.0296 0.088 Uiso 0.50 1 calc PR . .
C12 C 0.0000 0.5080(2) 0.3971(3) 0.0629(19) Uani 1 2 d S . .
H12A H 0.0977 0.5132 0.3593 0.094 Uiso 0.50 1 calc PR . .
H12B H 0.0259 0.5380 0.4382 0.094 Uiso 0.50 1 calc PR . .
H12C H -0.1237 0.5184 0.3758 0.094 Uiso 0.50 1 calc PR . .

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
I1 0.0750(3) 0.0370(2) 0.0278(2) -0.00102(12) 0.000 0.000
O1 0.105(4) 0.0270(17) 0.0277(16) -0.0067(14) 0.000 0.000
O2 0.128(4) 0.0277(18) 0.0392(19) -0.0012(16) 0.000 0.000
N1 0.070(3) 0.0253(19) 0.0272(19) -0.0032(15) 0.000 0.000
N2 0.062(3) 0.031(2) 0.0300(19) -0.0046(16) 0.000 0.000
C1 0.066(4) 0.027(2) 0.044(3) -0.013(2) 0.000 0.000
C2 0.066(4) 0.027(2) 0.044(3) -0.003(2) 0.000 0.000
C3 0.055(3) 0.030(2) 0.039(3) 0.0048(19) 0.000 0.000
C4 0.042(3) 0.028(2) 0.031(2) -0.0005(17) 0.000 0.000
C5 0.050(3) 0.031(2) 0.031(2) -0.0041(18) 0.000 0.000
C6 0.058(3) 0.030(2) 0.028(2) -0.0085(18) 0.000 0.000
C7 0.060(3) 0.025(2) 0.030(2) -0.0016(17) 0.000 0.000
C8 0.047(3) 0.031(2) 0.0226(19) -0.0039(17) 0.000 0.000
C9 0.036(2) 0.027(2) 0.034(2) -0.0033(17) 0.000 0.000
C10 0.067(4) 0.034(2) 0.030(2) -0.0009(19) 0.000 0.000
C11 0.110(5) 0.042(3) 0.024(2) 0.006(2) 0.000 0.000
C12 0.119(6) 0.025(3) 0.045(3) -0.007(2) 0.000 0.000

_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 C5 2.098(5) . ?
O1 C6 1.364(5) . ?
O1 C12 1.451(6) . ?
O2 C10 1.219(6) . ?
N1 C10 1.352(6) . ?
N1 C8 1.399(6) . ?
N1 H1A 0.9071 . ?
N2 C1 1.317(7) . ?
N2 C9 1.366(6) . ?
C1 C2 1.403(8) . ?
C1 H1 0.9300 . ?
C2 C3 1.347(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.417(6) . ?
C3 H3 0.9300 . ?
C4 C9 1.415(6) . ?
C4 C5 1.432(6) . ?
C5 C6 1.391(7) . ?
C6 C7 1.404(7) . ?
C7 C8 1.365(6) . ?
C7 H7 0.9300 . ?
C8 C9 1.432(7) . ?
C10 C11 1.504(7) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
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
C6 O1 C12 118.0(4) . . ?
C10 N1 C8 128.9(4) . . ?
C10 N1 H1A 118.1 . . ?
C8 N1 H1A 113.1 . . ?
C1 N2 C9 117.7(4) . . ?
N2 C1 C2 123.1(5) . . ?
N2 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C3 C2 C1 119.7(5) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C2 C3 C4 120.1(5) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C9 C4 C3 116.2(4) . . ?
C9 C4 C5 119.5(4) . . ?
C3 C4 C5 124.3(5) . . ?
C6 C5 C4 118.6(4) . . ?
C6 C5 I1 119.4(3) . . ?
C4 C5 I1 122.0(3) . . ?
O1 C6 C5 116.6(4) . . ?
O1 C6 C7 121.7(4) . . ?
C5 C6 C7 121.7(4) . . ?
C8 C7 C6 120.7(4) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 N1 124.0(4) . . ?
C7 C8 C9 119.8(4) . . ?
N1 C8 C9 116.2(4) . . ?
N2 C9 C4 123.2(4) . . ?
N2 C9 C8 117.0(4) . . ?
C4 C9 C8 119.8(4) . . ?
O2 C10 N1 123.5(5) . . ?
O2 C10 C11 122.2(5) . . ?
N1 C10 C11 114.2(4) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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
C9 N2 C1 C2 0.0 . . . . ?
N2 C1 C2 C3 0.000(1) . . . . ?
C1 C2 C3 C4 0.000(1) . . . . ?
C2 C3 C4 C9 0.000(1) . . . . ?
C2 C3 C4 C5 180.0 . . . . ?
C9 C4 C5 C6 0.000(1) . . . . ?
C3 C4 C5 C6 180.0 . . . . ?
C9 C4 C5 I1 180.0 . . . . ?
C3 C4 C5 I1 0.000(1) . . . . ?
C12 O1 C6 C5 180.0 . . . . ?
C12 O1 C6 C7 0.000(1) . . . . ?
C4 C5 C6 O1 180.0 . . . . ?
I1 C5 C6 O1 0.000(1) . . . . ?
C4 C5 C6 C7 0.000(1) . . . . ?
I1 C5 C6 C7 180.0 . . . . ?
O1 C6 C7 C8 180.000(1) . . . . ?
C5 C6 C7 C8 0.000(1) . . . . ?
C6 C7 C8 N1 180.0 . . . . ?
C6 C7 C8 C9 0.000(1) . . . . ?
C10 N1 C8 C7 0.000(1) . . . . ?
C10 N1 C8 C9 180.0 . . . . ?
C1 N2 C9 C4 0.0 . . . . ?
C1 N2 C9 C8 180.0 . . . . ?
C3 C4 C9 N2 0.0 . . . . ?
C5 C4 C9 N2 180.0 . . . . ?
C3 C4 C9 C8 180.0 . . . . ?
C5 C4 C9 C8 0.000(1) . . . . ?
C7 C8 C9 N2 180.0 . . . . ?
N1 C8 C9 N2 0.0 . . . . ?
C7 C8 C9 C4 0.000(1) . . . . ?
N1 C8 C9 C4 180.0 . . . . ?
C8 N1 C10 O2 0.000(1) . . . . ?
C8 N1 C10 C11 180.0 . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.60
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.734
_refine_diff_density_min         -0.758
_refine_diff_density_rms         0.108
