# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_01
_database_code_depnum_ccdc_archive 'CCDC 1437079'
_audit_update_record             
;
2015-11-16 deposited with the CCDC.
2018-05-24 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C9 H9 I2 N O2'
_chemical_formula_moiety         'C9 H9 I2 N O2'
_chemical_formula_weight         416.98
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_IT_number           61
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2+X,1/2-Y,-Z
3 -X,1/2+Y,1/2-Z
4 1/2-X,-Y,1/2+Z
5 -X,-Y,-Z
6 -1/2-X,-1/2+Y,+Z
7 +X,-1/2-Y,-1/2+Z
8 -1/2+X,+Y,-1/2-Z
#------------------------------------------------------------------------------
_cell_length_a                   12.0800
_cell_length_b                   11.7040
_cell_length_c                   16.1820
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     2287.8811
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6369
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    150
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_exptl_crystal_density_diffrn    2.421
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1536.00
_exptl_absorpt_coefficient_mu    5.476
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'NUMABS (Rigaku, 1999)'
_exptl_absorpt_correction_T_min  0.103
_exptl_absorpt_correction_T_max  0.193

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      150
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku XtaLAB mini'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 13.653
_diffrn_reflns_number            20398
_diffrn_reflns_av_R_equivalents  0.0807
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         3.030
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2620
_reflns_number_gt                2496
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0716
_refine_ls_wR_factor_ref         0.2096
_refine_ls_wR_factor_gt          0.2076
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2620
_refine_ls_number_parameters     127
_refine_ls_goodness_of_fit_ref   1.193
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0820P)²+55.3747P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.001
_refine_diff_density_max         3.43
_refine_diff_density_min         -2.81
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
I I -0.4742 1.8119
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
I1 I -0.05195(7) 1.16338(7) 0.13541(5) 0.0311(3) Uani 1 1 d . . . . .
I2 I 0.17729(8) 1.09930(8) 0.26361(6) 0.0408(3) Uani 1 1 d . . . . .
O7 O -0.0352(10) 0.9763(10) 0.3179(6) 0.052(3) Uani 1 1 d . . . . .
O8 O -0.0882(9) 0.8909(10) 0.2095(8) 0.055(3) Uani 1 1 d . . . . .
N3 N -0.0307(9) 0.9582(9) 0.2457(7) 0.033(2) Uani 1 1 d . . . . .
C6 C 0.0486(10) 1.0264(10) 0.1891(8) 0.029(2) Uani 1 1 d . . . . .
C12 C 0.1920(9) 0.7723(10) 0.0811(7) 0.028(2) Uani 1 1 d . . . . .
C13 C 0.0936(10) 0.9522(10) 0.1211(7) 0.028(2) Uani 1 1 d . . . . .
H13A H 0.1407 0.9995 0.0845 0.033 Uiso 1 1 calc R U . . .
H13B H 0.0309 0.9233 0.0876 0.033 Uiso 1 1 calc R U . . .
C14 C 0.1208(11) 0.6827(11) 0.0630(10) 0.043(3) Uani 1 1 d . . . . .
H14 H 0.0585 0.6677 0.0971 0.051 Uiso 1 1 calc R U . . .
C15 C 0.1427(14) 0.6131(12) -0.0079(11) 0.047(4) Uani 1 1 d . . . . .
H15 H 0.0932 0.5537 -0.0231 0.057 Uiso 1 1 calc R U . . .
C16 C 0.2356(15) 0.6333(13) -0.0530(9) 0.051(4) Uani 1 1 d . . . . .
H16 H 0.2515 0.5865 -0.0995 0.061 Uiso 1 1 calc R U . . .
C17 C 0.3065(12) 0.7200(13) -0.0327(9) 0.042(3) Uani 1 1 d . . . . .
H17 H 0.3712 0.7325 -0.0648 0.050 Uiso 1 1 calc R U . . .
C18 C 0.2842(11) 0.7897(10) 0.0347(8) 0.033(3) Uani 1 1 d . . . . .
H18 H 0.3337 0.8499 0.0484 0.039 Uiso 1 1 calc R U . . .
C19 C 0.1619(14) 0.8498(13) 0.1520(8) 0.044(4) Uani 1 1 d . . . . .
H19A H 0.2302 0.8776 0.1791 0.053 Uiso 1 1 calc R U . . .
H19B H 0.1185 0.8065 0.1934 0.053 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.0 r15 (Rigaku, 2011)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r15'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r15'
_computing_structure_solution    'Superflip (Palatinus, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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 C6 2.191(11) . ?
I2 C6 2.145(12) . ?
O7 N3 1.188(15) . ?
O8 N3 1.202(15) . ?
N3 C6 1.547(17) . ?
C6 C13 1.503(16) . ?
C12 C18 1.359(17) . ?
C12 C14 1.387(19) . ?
C12 C19 1.507(17) . ?
C13 C19 1.539(17) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 C15 1.43(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.36(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.37(2) . ?
C16 H16 0.9500 . ?
C17 C18 1.389(18) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?

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
O7 N3 O8 124.7(13) . . ?
O7 N3 C6 121.2(11) . . ?
O8 N3 C6 114.0(11) . . ?
C13 C6 N3 111.0(10) . . ?
C13 C6 I2 112.3(8) . . ?
N3 C6 I2 108.7(8) . . ?
C13 C6 I1 109.5(8) . . ?
N3 C6 I1 105.6(7) . . ?
I2 C6 I1 109.5(5) . . ?
C18 C12 C14 120.3(12) . . ?
C18 C12 C19 121.9(13) . . ?
C14 C12 C19 117.8(12) . . ?
C6 C13 C19 114.0(10) . . ?
C6 C13 H13A 108.8 . . ?
C19 C13 H13A 108.8 . . ?
C6 C13 H13B 108.8 . . ?
C19 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C12 C14 C15 119.0(13) . . ?
C12 C14 H14 120.5 . . ?
C15 C14 H14 120.5 . . ?
C16 C15 C14 118.9(14) . . ?
C16 C15 H15 120.5 . . ?
C14 C15 H15 120.5 . . ?
C15 C16 C17 121.2(14) . . ?
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C16 C17 C18 120.2(14) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C12 C18 C17 120.3(12) . . ?
C12 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C12 C19 C13 110.5(10) . . ?
C12 C19 H19A 109.5 . . ?
C13 C19 H19A 109.5 . . ?
C12 C19 H19B 109.5 . . ?
C13 C19 H19B 109.5 . . ?
H19A C19 H19B 108.1 . . ?

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
O7 N3 C6 C13 144.9(12) . . . . ?
O8 N3 C6 C13 -38.0(14) . . . . ?
O7 N3 C6 I2 20.9(14) . . . . ?
O8 N3 C6 I2 -162.0(10) . . . . ?
O7 N3 C6 I1 -96.5(12) . . . . ?
O8 N3 C6 I1 80.6(11) . . . . ?
N3 C6 C13 C19 -61.4(14) . . . . ?
I2 C6 C13 C19 60.5(13) . . . . ?
I1 C6 C13 C19 -177.6(10) . . . . ?
C18 C12 C14 C15 -3.5(18) . . . . ?
C19 C12 C14 C15 175.2(11) . . . . ?
C12 C14 C15 C16 3(2) . . . . ?
C14 C15 C16 C17 -1(2) . . . . ?
C15 C16 C17 C18 0(2) . . . . ?
C14 C12 C18 C17 1.8(18) . . . . ?
C19 C12 C18 C17 -176.8(12) . . . . ?
C16 C17 C18 C12 0(2) . . . . ?
C18 C12 C19 C13 87.0(16) . . . . ?
C14 C12 C19 C13 -91.7(15) . . . . ?
C6 C13 C19 C12 173.1(12) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

_shelxl_version_number           2013-4



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        (3,3-diiodo-3-nitropropyl)benzene
_chemical_properties_physical    
'Heat-sensitive, Oxygen-sensitive, Light-sensitive'
_exptl_crystal_preparation       'Magnetic properties'
