# 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_x
_database_code_depnum_ccdc_archive 'CCDC 1540968'
_audit_update_record             
;
2017-03-29 deposited with the CCDC.
2017-05-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C22 H17 I N2'
_chemical_formula_weight         436.28

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'
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   P21/N

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

_cell_length_a                   10.326(2)
_cell_length_b                   9.5840(19)
_cell_length_c                   19.601(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.43(3)
_cell_angle_gamma                90.00
_cell_volume                     1878.6(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25
_cell_measurement_theta_min      9
_cell_measurement_theta_max      14

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864
_exptl_absorpt_coefficient_mu    1.710
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_correction_T_min  0.7260
_exptl_absorpt_correction_T_max  0.8476
_exptl_absorpt_process_details   none

_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  'Nonius CAD4'
_diffrn_measurement_method       ω/2θ
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  2h
_diffrn_standards_decay_%        1
_diffrn_reflns_number            3638
_diffrn_reflns_av_R_equivalents  0.0950
_diffrn_reflns_av_sigmaI/netI    0.0691
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.05
_diffrn_reflns_theta_max         25.37
_reflns_number_total             3436
_reflns_number_gt                1915
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_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)+(0.0630P)²+0.0000P] 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     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3436
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1106
_refine_ls_R_factor_gt           0.0541
_refine_ls_wR_factor_ref         0.1370
_refine_ls_wR_factor_gt          0.1168
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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
I I 0.62264(5) 0.81561(6) 0.62235(2) 0.0749(2) Uani 1 1 d . . .
N1 N 0.5969(5) 0.6873(6) 0.2587(3) 0.0529(13) Uani 1 1 d . . .
C1 C 0.5971(6) 0.7853(7) 0.3988(3) 0.0524(17) Uani 1 1 d . . .
H1B H 0.5840 0.8482 0.3616 0.063 Uiso 1 1 calc R . .
N2 N 0.6120(5) 0.4699(6) 0.2222(3) 0.0549(14) Uani 1 1 d . . .
C2 C 0.5984(7) 0.8352(7) 0.4649(3) 0.0584(18) Uani 1 1 d . . .
H2A H 0.5841 0.9295 0.4717 0.070 Uiso 1 1 calc R . .
C3 C 0.6211(7) 0.7433(8) 0.5212(4) 0.0578(18) Uani 1 1 d . . .
C4 C 0.6404(7) 0.6043(8) 0.5097(3) 0.067(2) Uani 1 1 d . . .
H4A H 0.6563 0.5416 0.5471 0.080 Uiso 1 1 calc R . .
C5 C 0.6363(7) 0.5583(8) 0.4432(4) 0.0646(19) Uani 1 1 d . . .
H5A H 0.6486 0.4636 0.4364 0.078 Uiso 1 1 calc R . .
C6 C 0.6145(6) 0.6463(6) 0.3856(3) 0.0456(15) Uani 1 1 d . . .
C7 C 0.6099(6) 0.5977(7) 0.3143(3) 0.0504(16) Uani 1 1 d . . .
C8 C 0.6186(6) 0.4632(7) 0.2928(3) 0.0558(17) Uani 1 1 d . . .
H8A H 0.6273 0.3833 0.3205 0.067 Uiso 1 1 calc R . .
C9 C 0.5990(6) 0.6079(7) 0.2042(3) 0.0501(16) Uani 1 1 d . . .
C10 C 0.5968(6) 0.6622(6) 0.1334(3) 0.0493(16) Uani 1 1 d . . .
C11 C 0.6933(7) 0.6248(8) 0.0991(4) 0.075(2) Uani 1 1 d . . .
H11A H 0.7582 0.5595 0.1194 0.090 Uiso 1 1 calc R . .
C12 C 0.6942(9) 0.6838(10) 0.0348(4) 0.090(3) Uani 1 1 d . . .
H12A H 0.7620 0.6623 0.0130 0.108 Uiso 1 1 calc R . .
C13 C 0.5948(10) 0.7735(10) 0.0038(4) 0.084(3) Uani 1 1 d . . .
H13A H 0.5915 0.8085 -0.0409 0.100 Uiso 1 1 calc R . .
C14 C 0.5022(9) 0.8118(9) 0.0367(4) 0.093(3) Uani 1 1 d . . .
H14A H 0.4384 0.8778 0.0161 0.112 Uiso 1 1 calc R . .
C15 C 0.4994(9) 0.7549(10) 0.1011(4) 0.085(3) Uani 1 1 d . . .
H15A H 0.4317 0.7793 0.1225 0.102 Uiso 1 1 calc R . .
C16 C 0.5989(7) 0.3471(7) 0.1760(4) 0.064(2) Uani 1 1 d . . .
H16A H 0.6827 0.2961 0.1866 0.077 Uiso 1 1 calc R . .
H16B H 0.5804 0.3774 0.1273 0.077 Uiso 1 1 calc R . .
C17 C 0.4882(7) 0.2519(7) 0.1854(3) 0.0513(17) Uani 1 1 d . . .
C18 C 0.5140(7) 0.1137(8) 0.2045(3) 0.0626(19) Uani 1 1 d . . .
H18A H 0.6006 0.0790 0.2125 0.075 Uiso 1 1 calc R . .
C19 C 0.4103(11) 0.0268(9) 0.2117(4) 0.085(3) Uani 1 1 d . . .
H19A H 0.4282 -0.0658 0.2249 0.103 Uiso 1 1 calc R . .
C20 C 0.2821(11) 0.0763(12) 0.1996(5) 0.096(3) Uani 1 1 d . . .
H20A H 0.2133 0.0176 0.2044 0.116 Uiso 1 1 calc R . .
C21 C 0.2559(8) 0.2132(11) 0.1801(5) 0.088(3) Uani 1 1 d . . .
H21A H 0.1689 0.2471 0.1714 0.106 Uiso 1 1 calc R . .
C22 C 0.3595(8) 0.3016(9) 0.1734(4) 0.070(2) Uani 1 1 d . . .
H22A H 0.3414 0.3945 0.1607 0.084 Uiso 1 1 calc R . .


_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 C3 2.097(7) . ?
N1 C9 1.315(8) . ?
N1 C7 1.368(8) . ?
C1 C6 1.378(9) . ?
C1 C2 1.378(9) . ?
C1 H1B 0.9300 . ?
N2 C9 1.368(8) . ?
N2 C8 1.369(7) . ?
N2 C16 1.471(8) . ?
C2 C3 1.385(9) . ?
C2 H2A 0.9300 . ?
C3 C4 1.374(10) . ?
C4 C5 1.367(9) . ?
C4 H4A 0.9300 . ?
C5 C6 1.382(9) . ?
C5 H5A 0.9300 . ?
C6 C7 1.462(8) . ?
C7 C8 1.366(9) . ?
C8 H8A 0.9300 . ?
C9 C10 1.477(8) . ?
C10 C15 1.373(10) . ?
C10 C11 1.381(9) . ?
C11 C12 1.385(10) . ?
C11 H11A 0.9300 . ?
C12 C13 1.360(11) . ?
C12 H12A 0.9300 . ?
C13 C14 1.333(11) . ?
C13 H13A 0.9300 . ?
C14 C15 1.382(10) . ?
C14 H14A 0.9300 . ?
C15 H15A 0.9300 . ?
C16 C17 1.510(9) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C22 1.376(9) . ?
C17 C18 1.384(10) . ?
C18 C19 1.391(10) . ?
C18 H18A 0.9300 . ?
C19 C20 1.370(12) . ?
C19 H19A 0.9300 . ?
C20 C21 1.375(13) . ?
C20 H20A 0.9300 . ?
C21 C22 1.396(11) . ?
C21 H21A 0.9300 . ?
C22 H22A 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
C9 N1 C7 105.5(5) . . ?
C6 C1 C2 122.8(6) . . ?
C6 C1 H1B 118.6 . . ?
C2 C1 H1B 118.6 . . ?
C9 N2 C8 106.4(5) . . ?
C9 N2 C16 128.8(6) . . ?
C8 N2 C16 124.0(6) . . ?
C1 C2 C3 119.2(6) . . ?
C1 C2 H2A 120.4 . . ?
C3 C2 H2A 120.4 . . ?
C4 C3 C2 119.3(6) . . ?
C4 C3 I 120.6(5) . . ?
C2 C3 I 120.2(5) . . ?
C5 C4 C3 119.9(7) . . ?
C5 C4 H4A 120.1 . . ?
C3 C4 H4A 120.1 . . ?
C4 C5 C6 122.8(7) . . ?
C4 C5 H5A 118.6 . . ?
C6 C5 H5A 118.6 . . ?
C1 C6 C5 116.0(6) . . ?
C1 C6 C7 120.9(6) . . ?
C5 C6 C7 123.1(6) . . ?
C8 C7 N1 110.3(6) . . ?
C8 C7 C6 127.4(6) . . ?
N1 C7 C6 122.4(6) . . ?
C7 C8 N2 106.1(6) . . ?
C7 C8 H8A 126.9 . . ?
N2 C8 H8A 126.9 . . ?
N1 C9 N2 111.7(6) . . ?
N1 C9 C10 124.0(6) . . ?
N2 C9 C10 124.1(6) . . ?
C15 C10 C11 118.7(7) . . ?
C15 C10 C9 119.9(6) . . ?
C11 C10 C9 121.4(6) . . ?
C10 C11 C12 120.4(7) . . ?
C10 C11 H11A 119.8 . . ?
C12 C11 H11A 119.8 . . ?
C13 C12 C11 119.4(7) . . ?
C13 C12 H12A 120.3 . . ?
C11 C12 H12A 120.3 . . ?
C14 C13 C12 120.6(8) . . ?
C14 C13 H13A 119.7 . . ?
C12 C13 H13A 119.7 . . ?
C13 C14 C15 121.0(8) . . ?
C13 C14 H14A 119.5 . . ?
C15 C14 H14A 119.5 . . ?
C10 C15 C14 119.7(7) . . ?
C10 C15 H15A 120.1 . . ?
C14 C15 H15A 120.1 . . ?
N2 C16 C17 111.3(5) . . ?
N2 C16 H16A 109.4 . . ?
C17 C16 H16A 109.4 . . ?
N2 C16 H16B 109.4 . . ?
C17 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
C22 C17 C18 119.4(7) . . ?
C22 C17 C16 119.9(7) . . ?
C18 C17 C16 120.7(7) . . ?
C17 C18 C19 119.9(7) . . ?
C17 C18 H18A 120.0 . . ?
C19 C18 H18A 120.0 . . ?
C20 C19 C18 120.7(9) . . ?
C20 C19 H19A 119.7 . . ?
C18 C19 H19A 119.7 . . ?
C19 C20 C21 119.6(8) . . ?
C19 C20 H20A 120.2 . . ?
C21 C20 H20A 120.2 . . ?
C20 C21 C22 120.2(8) . . ?
C20 C21 H21A 119.9 . . ?
C22 C21 H21A 119.9 . . ?
C17 C22 C21 120.2(8) . . ?
C17 C22 H22A 119.9 . . ?
C21 C22 H22A 119.9 . . ?

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 1.6(10) . . . . ?
C1 C2 C3 C4 -0.7(10) . . . . ?
C1 C2 C3 I -179.7(5) . . . . ?
C2 C3 C4 C5 -0.4(11) . . . . ?
I C3 C4 C5 178.6(5) . . . . ?
C3 C4 C5 C6 0.7(11) . . . . ?
C2 C1 C6 C5 -1.3(10) . . . . ?
C2 C1 C6 C7 178.9(6) . . . . ?
C4 C5 C6 C1 0.1(10) . . . . ?
C4 C5 C6 C7 180.0(6) . . . . ?
C9 N1 C7 C8 -0.6(7) . . . . ?
C9 N1 C7 C6 178.9(5) . . . . ?
C1 C6 C7 C8 -176.4(6) . . . . ?
C5 C6 C7 C8 3.7(10) . . . . ?
C1 C6 C7 N1 4.2(9) . . . . ?
C5 C6 C7 N1 -175.7(6) . . . . ?
N1 C7 C8 N2 0.5(7) . . . . ?
C6 C7 C8 N2 -178.9(6) . . . . ?
C9 N2 C8 C7 -0.2(7) . . . . ?
C16 N2 C8 C7 -171.1(6) . . . . ?
C7 N1 C9 N2 0.4(7) . . . . ?
C7 N1 C9 C10 -175.7(6) . . . . ?
C8 N2 C9 N1 -0.1(7) . . . . ?
C16 N2 C9 N1 170.2(6) . . . . ?
C8 N2 C9 C10 176.0(6) . . . . ?
C16 N2 C9 C10 -13.7(10) . . . . ?
N1 C9 C10 C15 -52.5(10) . . . . ?
N2 C9 C10 C15 131.9(8) . . . . ?
N1 C9 C10 C11 125.7(7) . . . . ?
N2 C9 C10 C11 -49.9(10) . . . . ?
C15 C10 C11 C12 2.4(12) . . . . ?
C9 C10 C11 C12 -175.9(7) . . . . ?
C10 C11 C12 C13 -3.5(14) . . . . ?
C11 C12 C13 C14 4.4(14) . . . . ?
C12 C13 C14 C15 -4.1(15) . . . . ?
C11 C10 C15 C14 -2.1(12) . . . . ?
C9 C10 C15 C14 176.2(8) . . . . ?
C13 C14 C15 C10 3.0(15) . . . . ?
C9 N2 C16 C17 -119.7(7) . . . . ?
C8 N2 C16 C17 49.0(9) . . . . ?
N2 C16 C17 C22 58.9(9) . . . . ?
N2 C16 C17 C18 -122.5(7) . . . . ?
C22 C17 C18 C19 -0.3(10) . . . . ?
C16 C17 C18 C19 -178.9(6) . . . . ?
C17 C18 C19 C20 0.5(11) . . . . ?
C18 C19 C20 C21 -0.1(12) . . . . ?
C19 C20 C21 C22 -0.5(13) . . . . ?
C18 C17 C22 C21 -0.3(11) . . . . ?
C16 C17 C22 C21 178.3(7) . . . . ?
C20 C21 C22 C17 0.7(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.37
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.583
_refine_diff_density_rms         0.087
