# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_20140903ngd_0m
_database_code_depnum_ccdc_archive 'CCDC 1425989'
_audit_update_record             
;
2015-09-21 deposited with the CCDC.
2016-02-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H22 I2 N2 O3'
_chemical_formula_weight         556.17

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           Orthorhombic
_symmetry_space_group_name_H-M   'P2(1)2(1)2(1) '

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

_cell_length_a                   9.1833(5)
_cell_length_b                   10.6603(6)
_cell_length_c                   20.8558(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2041.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7090
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      28.00

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.15
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.809
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1072
_exptl_absorpt_coefficient_mu    3.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5763
_exptl_absorpt_correction_T_max  0.6538
_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            15181
_diffrn_reflns_av_R_equivalents  0.0301
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         1.95
_diffrn_reflns_theta_max         25.01
_reflns_number_total             3599
_reflns_number_gt                3451
_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-97 (Sheldrick, 2008)'
_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)+(0.0242P)²+0.2542P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(3)
_refine_ls_number_reflns         3599
_refine_ls_number_parameters     220
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0216
_refine_ls_R_factor_gt           0.0202
_refine_ls_wR_factor_ref         0.0487
_refine_ls_wR_factor_gt          0.0479
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_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
C1 C 0.1709(6) 0.8177(4) 0.0572(2) 0.0639(12) Uani 1 1 d . . .
H1 H 0.2493 0.7668 0.0682 0.077 Uiso 1 1 calc R . .
C2 C 0.1100(8) 0.8097(6) -0.0031(2) 0.094(2) Uani 1 1 d . . .
H2 H 0.1481 0.7548 -0.0335 0.112 Uiso 1 1 calc R . .
C3 C -0.0095(8) 0.8850(8) -0.0181(3) 0.112(3) Uani 1 1 d . . .
H3 H -0.0506 0.8806 -0.0587 0.134 Uiso 1 1 calc R . .
C4 C -0.0654(6) 0.9630(7) 0.0252(3) 0.092(2) Uani 1 1 d . . .
H4 H -0.1465 1.0109 0.0146 0.111 Uiso 1 1 calc R . .
C5 C -0.0041(5) 0.9743(5) 0.0865(2) 0.0650(13) Uani 1 1 d . . .
H5 H -0.0427 1.0295 0.1165 0.078 Uiso 1 1 calc R . .
C6 C 0.1155(4) 0.9008(4) 0.10086(18) 0.0454(9) Uani 1 1 d . . .
C7 C 0.1109(4) 0.9136(3) 0.21747(19) 0.0444(9) Uani 1 1 d . . .
C8 C 0.1350(5) 0.9465(4) 0.33287(17) 0.0494(9) Uani 1 1 d . . .
C9 C 0.0174(6) 1.0439(6) 0.3387(3) 0.099(2) Uani 1 1 d . . .
H9A H 0.0474 1.1193 0.3173 0.149 Uiso 1 1 calc R . .
H9B H 0.0000 1.0617 0.3832 0.149 Uiso 1 1 calc R . .
H9C H -0.0705 1.0131 0.3194 0.149 Uiso 1 1 calc R . .
C10 C 0.0824(6) 0.8156(5) 0.3497(2) 0.0803(17) Uani 1 1 d . . .
H10A H -0.0096 0.8004 0.3293 0.120 Uiso 1 1 calc R . .
H10B H 0.0714 0.8088 0.3953 0.120 Uiso 1 1 calc R . .
H10C H 0.1523 0.7550 0.3351 0.120 Uiso 1 1 calc R . .
C11 C 0.2658(6) 0.9803(6) 0.3713(2) 0.0700(14) Uani 1 1 d . . .
H11A H 0.3384 0.9160 0.3667 0.105 Uiso 1 1 calc R . .
H11B H 0.2392 0.9877 0.4157 0.105 Uiso 1 1 calc R . .
H11C H 0.3043 1.0587 0.3564 0.105 Uiso 1 1 calc R . .
C12 C 0.3429(4) 0.9340(3) 0.15822(16) 0.0357(7) Uani 1 1 d . . .
C13 C 0.4364(3) 0.8485(3) 0.18084(17) 0.0362(7) Uani 1 1 d . . .
C14 C 0.4535(6) 1.0402(5) 0.0650(2) 0.0758(15) Uani 1 1 d . . .
H14A H 0.5223 0.9713 0.0627 0.091 Uiso 1 1 calc R . .
H14B H 0.3782 1.0258 0.0332 0.091 Uiso 1 1 calc R . .
C15 C 0.5278(8) 1.1577(6) 0.0513(3) 0.101(2) Uani 1 1 d . . .
H15A H 0.6101 1.1660 0.0801 0.121 Uiso 1 1 calc R . .
H15B H 0.5654 1.1547 0.0078 0.121 Uiso 1 1 calc R . .
C16 C 0.3810(8) 1.2699(5) 0.1211(4) 0.099(2) Uani 1 1 d . . .
H16A H 0.3174 1.3423 0.1244 0.119 Uiso 1 1 calc R . .
H16B H 0.4604 1.2815 0.1512 0.119 Uiso 1 1 calc R . .
C17 C 0.2982(5) 1.1557(4) 0.1391(3) 0.0681(13) Uani 1 1 d . . .
H17A H 0.2695 1.1606 0.1837 0.082 Uiso 1 1 calc R . .
H17B H 0.2106 1.1498 0.1132 0.082 Uiso 1 1 calc R . .
I1 I 0.37235(3) 0.67305(2) 0.214663(13) 0.04840(8) Uani 1 1 d . . .
I2 I 0.66053(2) 0.87903(2) 0.187027(13) 0.04679(8) Uani 1 1 d . . .
N1 N 0.1889(3) 0.9140(3) 0.16128(14) 0.0396(7) Uani 1 1 d . . .
N2 N 0.3883(4) 1.0448(3) 0.12890(14) 0.0429(7) Uani 1 1 d . . .
O1 O 0.4388(6) 1.2636(4) 0.0576(2) 0.1040(15) Uani 1 1 d . . .
O2 O -0.0178(3) 0.8894(3) 0.21959(14) 0.0637(8) Uani 1 1 d . . .
O3 O 0.1933(3) 0.9457(2) 0.26655(11) 0.0425(6) 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 C6 1.368(6) . ?
C1 C2 1.380(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.395(11) . ?
C2 H2 0.9300 . ?
C3 C4 1.329(10) . ?
C3 H3 0.9300 . ?
C4 C5 1.402(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(6) . ?
C5 H5 0.9300 . ?
C6 N1 1.436(5) . ?
C7 O2 1.210(4) . ?
C7 O3 1.318(4) . ?
C7 N1 1.373(5) . ?
C8 O3 1.483(4) . ?
C8 C11 1.488(6) . ?
C8 C9 1.504(6) . ?
C8 C10 1.518(6) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.337(5) . ?
C12 N2 1.395(4) . ?
C12 N1 1.432(4) . ?
C13 I1 2.084(3) . ?
C13 I2 2.088(3) . ?
C14 C15 1.454(8) . ?
C14 N2 1.462(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 O1 1.400(8) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 O1 1.429(8) . ?
C16 C17 1.484(7) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 N2 1.458(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 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
C6 C1 C2 119.7(5) . . ?
C6 C1 H1 120.1 . . ?
C2 C1 H1 120.1 . . ?
C1 C2 C3 119.1(6) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C4 C3 C2 120.8(5) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 121.2(6) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 117.9(6) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
C1 C6 C5 121.2(4) . . ?
C1 C6 N1 118.2(4) . . ?
C5 C6 N1 120.5(4) . . ?
O2 C7 O3 126.0(4) . . ?
O2 C7 N1 122.7(4) . . ?
O3 C7 N1 111.2(3) . . ?
O3 C8 C11 102.3(3) . . ?
O3 C8 C9 109.8(4) . . ?
C11 C8 C9 111.7(4) . . ?
O3 C8 C10 109.0(3) . . ?
C11 C8 C10 110.7(4) . . ?
C9 C8 C10 112.8(4) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C8 C10 H10A 109.5 . . ?
C8 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C8 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 N2 122.7(3) . . ?
C13 C12 N1 121.1(3) . . ?
N2 C12 N1 116.2(3) . . ?
C12 C13 I1 123.3(2) . . ?
C12 C13 I2 123.3(2) . . ?
I1 C13 I2 113.39(15) . . ?
C15 C14 N2 110.0(5) . . ?
C15 C14 H14A 109.7 . . ?
N2 C14 H14A 109.7 . . ?
C15 C14 H14B 109.7 . . ?
N2 C14 H14B 109.7 . . ?
H14A C14 H14B 108.2 . . ?
O1 C15 C14 113.7(5) . . ?
O1 C15 H15A 108.8 . . ?
C14 C15 H15A 108.8 . . ?
O1 C15 H15B 108.8 . . ?
C14 C15 H15B 108.8 . . ?
H15A C15 H15B 107.7 . . ?
O1 C16 C17 112.7(5) . . ?
O1 C16 H16A 109.1 . . ?
C17 C16 H16A 109.1 . . ?
O1 C16 H16B 109.1 . . ?
C17 C16 H16B 109.1 . . ?
H16A C16 H16B 107.8 . . ?
N2 C17 C16 109.7(4) . . ?
N2 C17 H17A 109.7 . . ?
C16 C17 H17A 109.7 . . ?
N2 C17 H17B 109.7 . . ?
C16 C17 H17B 109.7 . . ?
H17A C17 H17B 108.2 . . ?
C7 N1 C12 123.6(3) . . ?
C7 N1 C6 120.3(3) . . ?
C12 N1 C6 116.0(3) . . ?
C12 N2 C17 117.0(3) . . ?
C12 N2 C14 119.6(3) . . ?
C17 N2 C14 113.1(4) . . ?
C15 O1 C16 110.0(4) . . ?
C7 O3 C8 121.2(3) . . ?

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 -1.4(8) . . . . ?
C1 C2 C3 C4 -0.5(9) . . . . ?
C2 C3 C4 C5 1.5(10) . . . . ?
C3 C4 C5 C6 -0.6(8) . . . . ?
C2 C1 C6 C5 2.3(7) . . . . ?
C2 C1 C6 N1 -175.0(4) . . . . ?
C4 C5 C6 C1 -1.3(7) . . . . ?
C4 C5 C6 N1 175.9(4) . . . . ?
N2 C12 C13 I1 -172.3(2) . . . . ?
N1 C12 C13 I1 5.8(5) . . . . ?
N2 C12 C13 I2 8.7(5) . . . . ?
N1 C12 C13 I2 -173.2(2) . . . . ?
N2 C14 C15 O1 -55.3(7) . . . . ?
O1 C16 C17 N2 53.7(7) . . . . ?
O2 C7 N1 C12 -175.6(4) . . . . ?
O3 C7 N1 C12 6.0(5) . . . . ?
O2 C7 N1 C6 7.9(6) . . . . ?
O3 C7 N1 C6 -170.4(3) . . . . ?
C13 C12 N1 C7 69.1(5) . . . . ?
N2 C12 N1 C7 -112.7(4) . . . . ?
C13 C12 N1 C6 -114.3(4) . . . . ?
N2 C12 N1 C6 63.9(4) . . . . ?
C1 C6 N1 C7 -133.2(4) . . . . ?
C5 C6 N1 C7 49.5(5) . . . . ?
C1 C6 N1 C12 50.0(5) . . . . ?
C5 C6 N1 C12 -127.2(4) . . . . ?
C13 C12 N2 C17 -145.7(4) . . . . ?
N1 C12 N2 C17 36.1(5) . . . . ?
C13 C12 N2 C14 71.7(5) . . . . ?
N1 C12 N2 C14 -106.5(4) . . . . ?
C16 C17 N2 C12 164.0(4) . . . . ?
C16 C17 N2 C14 -51.0(6) . . . . ?
C15 C14 N2 C12 -164.5(4) . . . . ?
C15 C14 N2 C17 51.6(6) . . . . ?
C14 C15 O1 C16 58.1(7) . . . . ?
C17 C16 O1 C15 -57.0(7) . . . . ?
O2 C7 O3 C8 4.4(6) . . . . ?
N1 C7 O3 C8 -177.3(3) . . . . ?
C11 C8 O3 C7 176.8(4) . . . . ?
C9 C8 O3 C7 -64.4(5) . . . . ?
C10 C8 O3 C7 59.6(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.432
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.080
