data_global

_publ_section_references
;
Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R., Towler, M. (2004). 
J. Appl. Cryst., 37, 335--338.

Bruker (2016). Apex3 v2016.9-0, SAINT V8.37A, Bruker AXS 
Inc.: Madison (WI), USA, 2013/2014.

Hübschle, C. B., Sheldrick, G. M. and Dittrich, B. (2011). J. Appl. Cryst., 
44, 1281--1284.

Sheldrick, G.M. (2008). Acta Cryst., A64, 112--122.

Sheldrick, G. M. (2018). SHELXL2018. University of Göttingen, Germany.

Sheldrick G. M. (2015). "Crystal structure refinement with SHELXL", Acta Cryst., 
C71, 3--8.

Sheldrick, G. M. (2012). TWINABS. Ver. 2012/1. (Sheldrick, 2012)

Spek, A. L. (2003). J. Appl. Cryst., 36, 7--13.

CSD: Groom, C. R. & Allen, F. H. (2014). Angew. Chem. Int. Ed., 53, 662--671.

Publcif: Westrip, S. P. (2010). J. Appl. Cryst., 43, 920--925.
;

_publ_section_acknowledgements
;
This material is based upon work supported by the National Science Foundation 
through the Major Research Instrumentation Program under Grant No. CHE 1625543.
(Funding for the single crystal X-ray diffractometer).
;

data_RS54_0m
 
_audit_creation_method            'SHELXL-2018/1'
_shelx_SHELXL_version_number      '2018/1'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          ?
_chemical_formula_sum
 'C7 H10 I2 N2 O' 
_chemical_formula_weight          391.97

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'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 '-x, -y, -z'
 
_cell_length_a                    8.2802(5)
_cell_length_b                    8.4250(5)
_cell_length_c                    9.0335(5)
_cell_angle_alpha                 87.808(2)
_cell_angle_beta                  71.668(2)
_cell_angle_gamma                 67.280(2)
_cell_volume                      549.28(6)
_cell_formula_units_Z             2
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     8480      
_cell_measurement_theta_min       3.0062 
_cell_measurement_theta_max       32.2125
 
_exptl_crystal_description        block
_exptl_crystal_colour             red
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     2.370          
_exptl_crystal_F_000              360
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.150
_exptl_crystal_size_mid           0.140
_exptl_crystal_size_min           0.110
_exptl_absorpt_coefficient_mu     5.687
_shelx_estimated_absorpt_T_min    0.483
_shelx_estimated_absorpt_T_max    0.574
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.6826
_exptl_absorpt_correction_T_max   0.7465
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'sealed tube X-ray source'
_diffrn_radiation_monochromator   'Triumph curved graphite crystal'
_diffrn_measurement_device_type   'Bruker AXS D8 Quest CMOS diffractometer' 
_diffrn_measurement_method        'omega and phi scans'
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             22702
_diffrn_reflns_av_unetI/netI      0.0340
_diffrn_reflns_av_R_equivalents   0.0405
_diffrn_reflns_limit_h_min        -12
_diffrn_reflns_limit_h_max        12
_diffrn_reflns_limit_k_min        -12
_diffrn_reflns_limit_k_max        12
_diffrn_reflns_limit_l_min        -13
_diffrn_reflns_limit_l_max        13
_diffrn_reflns_theta_min          3.719
_diffrn_reflns_theta_max          33.210
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.991
_diffrn_measured_fraction_theta_full  0.996
_diffrn_reflns_Laue_measured_fraction_max    0.991
_diffrn_reflns_Laue_measured_fraction_full   0.996
_diffrn_reflns_point_group_measured_fraction_max   0.991
_diffrn_reflns_point_group_measured_fraction_full  0.996
_reflns_number_total              4172
_reflns_number_gt                 3161
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'Apex3 v2016.9-0 (Bruker, 2016)' 
_computing_cell_refinement        'SAINT V8.37A (Bruker, 2016)' 
_computing_data_reduction         'SAINT V8.37A (Bruker, 2016)'
_computing_structure_solution     'SHELXS-97 (Sheldrick, 2008)' 
_computing_structure_refinement   
;  
SHELXL-2018/1 (Sheldrick, 2015, 2018), 
SHELXLE Rev882 (Hübschle et al., 2011)
; 
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0128P)²+0.3528P] 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      'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_coef        0.0067(3)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          4172
_refine_ls_number_parameters      112
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0489
_refine_ls_R_factor_gt            0.0264
_refine_ls_wR_factor_ref          0.0441
_refine_ls_wR_factor_gt           0.0399
_refine_ls_goodness_of_fit_ref    1.032
_refine_ls_restrained_S_all       1.032
_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_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
C1 C 0.5394(3) 0.2290(3) 0.0508(3) 0.0270(5) Uani 1 1 d . . . . .
H1 H 0.566031 0.304154 -0.025380 0.032 Uiso 1 1 calc R U . . .
C2 C 0.6705(3) 0.0668(3) 0.0432(3) 0.0226(4) Uani 1 1 d . . . . .
H2 H 0.785252 0.029382 -0.039726 0.027 Uiso 1 1 calc R U . . .
C3 C 0.6368(3) -0.0460(3) 0.1578(2) 0.0198(4) Uani 1 1 d . . . . .
C4 C 0.4589(3) 0.0174(3) 0.2730(3) 0.0260(5) Uani 1 1 d . . . . .
H4 H 0.427224 -0.053938 0.351188 0.031 Uiso 1 1 calc R U . . .
C5 C 0.3329(3) 0.1794(3) 0.2728(3) 0.0291(5) Uani 1 1 d . . . . .
H5 H 0.214257 0.219330 0.350782 0.035 Uiso 1 1 calc R U . . .
C6 C 0.9474(3) -0.2626(3) 0.0375(3) 0.0285(5) Uani 1 1 d . . . . .
H6A H 1.029264 -0.372434 0.062249 0.043 Uiso 1 1 calc R U . . .
H6B H 1.000337 -0.176069 0.033681 0.043 Uiso 1 1 calc R U . . .
H6C H 0.934560 -0.279043 -0.064369 0.043 Uiso 1 1 calc R U . . .
C7 C 0.7306(4) -0.3171(3) 0.2783(3) 0.0383(6) Uani 1 1 d . . . . .
H7A H 0.685394 -0.254504 0.381961 0.057 Uiso 1 1 calc R U . . .
H7B H 0.845404 -0.418151 0.267550 0.057 Uiso 1 1 calc R U . . .
H7C H 0.637076 -0.355126 0.266392 0.057 Uiso 1 1 calc R U . . .
I1 I 0.21527(2) 0.62616(2) 0.37590(2) 0.02540(5) Uani 1 1 d . . . . .
I2 I 0.18612(3) 0.83372(2) 0.62498(2) 0.03764(6) Uani 1 1 d . . . . .
N1 N 0.3737(3) 0.2843(2) 0.1638(2) 0.0274(4) Uani 1 1 d . . . . .
N2 N 0.7663(3) -0.2037(2) 0.1578(2) 0.0235(4) Uani 1 1 d . . . . .
O1 O 0.2465(3) 0.4459(2) 0.1664(2) 0.0374(4) 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 N1 1.343(3) . ?
C1 C2 1.365(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.414(3) . ?
C2 H2 0.9500 . ?
C3 N2 1.347(3) . ?
C3 C4 1.417(3) . ?
C4 C5 1.361(3) . ?
C4 H4 0.9500 . ?
C5 N1 1.349(3) . ?
C5 H5 0.9500 . ?
C6 N2 1.455(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 N2 1.457(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
I1 O1 2.3588(18) . ?
I1 I2 2.7951(3) . ?
N1 O1 1.357(2) . ?
 
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
N1 C1 C2 121.3(2) . . ?
N1 C1 H1 119.3 . . ?
C2 C1 H1 119.3 . . ?
C1 C2 C3 120.5(2) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
N2 C3 C2 122.0(2) . . ?
N2 C3 C4 122.1(2) . . ?
C2 C3 C4 115.9(2) . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
N1 C5 C4 121.1(2) . . ?
N1 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
N2 C6 H6A 109.5 . . ?
N2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
N2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 I1 I2 178.62(4) . . ?
C1 N1 C5 120.3(2) . . ?
C1 N1 O1 119.5(2) . . ?
C5 N1 O1 120.2(2) . . ?
C3 N2 C6 120.06(19) . . ?
C3 N2 C7 121.3(2) . . ?
C6 N2 C7 118.60(19) . . ?
N1 O1 I1 110.11(12) . . ?
 
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
N1 C1 C2 C3 -1.9(3) . . . . ?
C1 C2 C3 N2 -176.8(2) . . . . ?
C1 C2 C3 C4 2.8(3) . . . . ?
N2 C3 C4 C5 177.9(2) . . . . ?
C2 C3 C4 C5 -1.7(3) . . . . ?
C3 C4 C5 N1 -0.3(4) . . . . ?
C2 C1 N1 C5 -0.2(3) . . . . ?
C2 C1 N1 O1 -179.4(2) . . . . ?
C4 C5 N1 C1 1.3(3) . . . . ?
C4 C5 N1 O1 -179.5(2) . . . . ?
C2 C3 N2 C6 0.0(3) . . . . ?
C4 C3 N2 C6 -179.6(2) . . . . ?
C2 C3 N2 C7 178.9(2) . . . . ?
C4 C3 N2 C7 -0.7(3) . . . . ?
C1 N1 O1 I1 -108.00(19) . . . . ?
C5 N1 O1 I1 72.8(2) . . . . ?
 
_refine_diff_density_max    0.928
_refine_diff_density_min   -0.737
_refine_diff_density_rms    0.134



