# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 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. 
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data_nrv15
_database_code_depnum_ccdc_archive 'CCDC 1844327'
_audit_update_record             
;
2018-05-21 deposited with the CCDC.
2018-08-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_name_systematic        1-Iodo-5-nitroisoquinoline
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H5 I N2 O2'
_chemical_formula_weight         300.05

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 '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                   7.6101(13)
_cell_length_b                   8.0298(7)
_cell_length_c                   8.5371(9)
_cell_angle_alpha                81.120(6)
_cell_angle_beta                 65.955(12)
_cell_angle_gamma                73.612(11)
_cell_volume                     456.60(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1700
_cell_measurement_theta_min      5
_cell_measurement_theta_max      71

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.182
_exptl_crystal_F_000             284
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    27.362
_shelx_estimated_absorpt_T_min   0.065
_shelx_estimated_absorpt_T_max   0.171
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.201
_exptl_absorpt_correction_T_max  0.648
_exptl_absorpt_process_details   'SCALEPACK (Otwinowski & Minor, 1997)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'microfocus X-ray tube'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_measurement_device_type  
'Rigaku Rapid II curved image plate diffractometer'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            1677
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_av_R_equivalents  0.0710
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         5.680
_diffrn_reflns_theta_max         71.955
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.933
_diffrn_measured_fraction_theta_full 0.949
_diffrn_reflns_Laue_measured_fraction_max 0.933
_diffrn_reflns_Laue_measured_fraction_full 0.949
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_point_group_measured_fraction_full 0.949
_reflns_number_total             1677
_reflns_number_gt                1666
_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       'CrystalClear (Rigaku, 2001)'
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1996)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1996)'
_computing_structure_solution    'PATTY (DIRDIF, Beurskins, 2008)'
_computing_structure_refinement  
;  
SHELXL-2017/1 (Sheldrick, 2017), 
SHELXLE Rev816 (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)+(0.0653P)²+0.9916P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     patt
_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         1677
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0364
_refine_ls_wR_factor_ref         0.0973
_refine_ls_wR_factor_gt          0.0972
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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_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 0.22352(5) 0.33757(4) 0.16772(3) 0.04524(17) Uani 1 1 d . . . . .
O1 O 0.3724(8) -0.4184(6) 0.7244(6) 0.0618(12) Uani 1 1 d . . . . .
O2 O 0.1902(7) -0.2944(6) 0.9636(5) 0.0565(11) Uani 1 1 d . . . . .
N1 N 0.2735(6) -0.2885(6) 0.8059(5) 0.0365(8) Uani 1 1 d . . . . .
N2 N 0.2664(6) -0.0353(6) 0.2096(5) 0.0378(9) Uani 1 1 d . . . . .
C1 C 0.2470(7) 0.0913(6) 0.2985(5) 0.0314(9) Uani 1 1 d . . . . .
C3 C 0.2830(8) -0.1967(7) 0.2836(6) 0.0404(11) Uani 1 1 d . . . . .
H3 H 0.296716 -0.289368 0.219206 0.048 Uiso 1 1 calc R U . . .
C4 C 0.2814(7) -0.2355(6) 0.4465(6) 0.0351(9) Uani 1 1 d . . . . .
H4 H 0.293574 -0.351909 0.492177 0.042 Uiso 1 1 calc R U . . .
C5 C 0.2613(6) -0.1002(6) 0.5457(5) 0.0269(8) Uani 1 1 d . . . . .
C6 C 0.2550(6) -0.1177(6) 0.7163(5) 0.0300(9) Uani 1 1 d . . . . .
C7 C 0.2331(7) 0.0194(7) 0.8046(5) 0.0362(10) Uani 1 1 d . . . . .
H7 H 0.226672 0.001868 0.919298 0.043 Uiso 1 1 calc R U . . .
C8 C 0.2203(7) 0.1857(6) 0.7259(6) 0.0378(10) Uani 1 1 d . . . . .
H8 H 0.208409 0.281037 0.786015 0.045 Uiso 1 1 calc R U . . .
C9 C 0.2247(7) 0.2120(6) 0.5612(5) 0.0345(9) Uani 1 1 d . . . . .
H9 H 0.215190 0.325751 0.508732 0.041 Uiso 1 1 calc R U . . .
C10 C 0.2433(6) 0.0712(6) 0.4693(5) 0.0280(8) 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
I1 C1 2.114(5) . ?
O1 N1 1.222(6) . ?
O2 N1 1.233(5) . ?
N1 C6 1.463(6) . ?
N2 C1 1.302(6) . ?
N2 C3 1.347(7) . ?
C1 C10 1.431(6) . ?
C3 C4 1.373(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.416(6) . ?
C4 H4 0.9500 . ?
C5 C6 1.424(6) . ?
C5 C10 1.424(6) . ?
C6 C7 1.364(6) . ?
C7 C8 1.395(7) . ?
C7 H7 0.9500 . ?
C8 C9 1.376(6) . ?
C8 H8 0.9500 . ?
C9 C10 1.417(6) . ?
C9 H9 0.9500 . ?

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
O1 N1 O2 122.4(5) . . ?
O1 N1 C6 119.9(4) . . ?
O2 N1 C6 117.7(4) . . ?
C1 N2 C3 117.8(4) . . ?
N2 C1 C10 124.6(4) . . ?
N2 C1 I1 114.1(3) . . ?
C10 C1 I1 121.3(3) . . ?
N2 C3 C4 124.0(4) . . ?
N2 C3 H3 118.0 . . ?
C4 C3 H3 118.0 . . ?
C3 C4 C5 119.3(4) . . ?
C3 C4 H4 120.3 . . ?
C5 C4 H4 120.3 . . ?
C4 C5 C6 126.5(4) . . ?
C4 C5 C10 117.3(4) . . ?
C6 C5 C10 116.2(4) . . ?
C7 C6 C5 123.1(4) . . ?
C7 C6 N1 116.4(4) . . ?
C5 C6 N1 120.5(4) . . ?
C6 C7 C8 119.7(4) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C9 C8 C7 120.2(4) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C10 120.7(4) . . ?
C8 C9 H9 119.7 . . ?
C10 C9 H9 119.7 . . ?
C9 C10 C5 120.1(4) . . ?
C9 C10 C1 123.0(4) . . ?
C5 C10 C1 116.9(4) . . ?

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
C3 N2 C1 C10 0.4(7) . . . . ?
C3 N2 C1 I1 179.8(3) . . . . ?
C1 N2 C3 C4 -0.2(7) . . . . ?
N2 C3 C4 C5 0.0(8) . . . . ?
C3 C4 C5 C6 179.4(4) . . . . ?
C3 C4 C5 C10 0.1(6) . . . . ?
C4 C5 C6 C7 -179.3(4) . . . . ?
C10 C5 C6 C7 0.0(6) . . . . ?
C4 C5 C6 N1 1.2(7) . . . . ?
C10 C5 C6 N1 -179.6(4) . . . . ?
O1 N1 C6 C7 -148.9(5) . . . . ?
O2 N1 C6 C7 29.7(6) . . . . ?
O1 N1 C6 C5 30.7(7) . . . . ?
O2 N1 C6 C5 -150.8(4) . . . . ?
C5 C6 C7 C8 -1.4(7) . . . . ?
N1 C6 C7 C8 178.2(4) . . . . ?
C6 C7 C8 C9 1.6(7) . . . . ?
C7 C8 C9 C10 -0.3(7) . . . . ?
C8 C9 C10 C5 -1.2(7) . . . . ?
C8 C9 C10 C1 179.5(4) . . . . ?
C4 C5 C10 C9 -179.4(4) . . . . ?
C6 C5 C10 C9 1.3(6) . . . . ?
C4 C5 C10 C1 0.0(6) . . . . ?
C6 C5 C10 C1 -179.3(4) . . . . ?
N2 C1 C10 C9 179.1(4) . . . . ?
I1 C1 C10 C9 -0.3(6) . . . . ?
N2 C1 C10 C5 -0.3(7) . . . . ?
I1 C1 C10 C5 -179.6(3) . . . . ?

_refine_diff_density_max         0.909
_refine_diff_density_min         -1.455
_refine_diff_density_rms         0.127

