# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2020

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 1992507'
loop_
_audit_author_name
_audit_author_address
'David Cordes'
;University of St Andrews
United Kingdom
;
_audit_update_record             
;
2020-03-24 deposited with the CCDC.	2020-05-14 downloaded from the CCDC.
;
_audit_creation_date             2020-03-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H10 I N O2'
_chemical_formula_sum            'C20 H10 I N O2'
_chemical_formula_weight         423.19
_chemical_melting_point          ?

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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        P-1
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0823(2)
_cell_length_b                   8.3105(2)
_cell_length_c                   11.8907(4)
_cell_angle_alpha                83.340(2)
_cell_angle_beta                 80.164(2)
_cell_angle_gamma                69.285(2)
_cell_volume                     734.72(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5658
_cell_measurement_temperature    173
_cell_measurement_theta_max      28.7190
_cell_measurement_theta_min      2.6040
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.192
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91378
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.913
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             412
_exptl_crystal_size_max          0.09
_exptl_crystal_size_mid          0.03
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.830
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            9702
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.830
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.025
_diffrn_reflns_theta_min         1.741
_diffrn_ambient_temperature      173
_diffrn_detector                 'hybrid photon counting detector'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.830
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω   -100.00  80.00   0.50    5.00    --  -10.00  45.00   0.00  360
  2  ω   -100.00  80.00   0.50    5.00    --  -10.00  45.00  90.00  360
  3  ω   -100.00  80.00   0.50    5.00    --  -10.00  45.00 180.00  360
;
_diffrn_measurement_device       'AFC10: Fixed chi 2 circle'
_diffrn_measurement_device_type  'Rigaku XtaLAB P200K'
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_specimen_support Loop
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0656939000
_diffrn_orient_matrix_UB_12      0.0835491000
_diffrn_orient_matrix_UB_13      0.0006305000
_diffrn_orient_matrix_UB_21      0.0567134000
_diffrn_orient_matrix_UB_22      0.0305586000
_diffrn_orient_matrix_UB_23      -0.0424669000
_diffrn_orient_matrix_UB_31      -0.0380333000
_diffrn_orient_matrix_UB_32      -0.0210367000
_diffrn_orient_matrix_UB_33      -0.0432995000
_diffrn_radiation_monochromator  'Rigaku Osmic Confocal Optical System'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Rotating Anode'
_diffrn_source_type              'Rigaku FR-X'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2827
_reflns_number_total             3241
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       
'CrystalClear-SM Expert 2.1 b45 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_refine_diff_density_max         2.133
_refine_diff_density_min         -0.643
_refine_diff_density_rms         0.112
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3241
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0403
_refine_ls_R_factor_gt           0.0326
_refine_ls_restrained_S_all      1.079
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0395P)²+0.4396P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0771
_refine_ls_wR_factor_ref         0.0795
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C10(H10), C11(H11), C12(H12), C16(H16), C17(H17),
 C18(H18), C19(H19)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
I5 I 0.95856(3) 0.27035(3) 0.56839(2) 0.02722(10) Uani 1 1 d . . . . .
O8 O 0.5921(4) -0.0428(3) 0.3573(2) 0.0359(7) Uani 1 1 d . . . . .
O14 O -0.0825(3) 0.6517(3) 0.1068(2) 0.0352(6) Uani 1 1 d . . . . .
N1 N 0.3989(3) 0.4499(3) 0.2241(2) 0.0186(6) Uani 1 1 d . . . . .
C2 C 0.5254(4) 0.4124(4) 0.3012(3) 0.0191(7) Uani 1 1 d . . . . .
C3 C 0.5785(4) 0.5412(4) 0.3347(3) 0.0207(7) Uani 1 1 d . . . . .
H3 H 0.530551 0.656587 0.304682 0.025 Uiso 1 1 calc R . . . .
C4 C 0.6996(4) 0.5009(4) 0.4105(3) 0.0213(7) Uani 1 1 d . . . . .
H4 H 0.736940 0.588113 0.431628 0.026 Uiso 1 1 calc R . . . .
C5 C 0.7682(4) 0.3324(4) 0.4568(3) 0.0207(7) Uani 1 1 d . . . . .
C6 C 0.7123(4) 0.2068(4) 0.4293(3) 0.0211(7) Uani 1 1 d . . . . .
H6 H 0.756939 0.093224 0.463100 0.025 Uiso 1 1 calc R . . . .
C7 C 0.5891(4) 0.2446(4) 0.3514(3) 0.0201(7) Uani 1 1 d . . . . .
C8 C 0.5210(5) 0.1093(4) 0.3306(3) 0.0241(7) Uani 1 1 d . . . . .
C9 C 0.3542(4) 0.1755(4) 0.2787(3) 0.0200(7) Uani 1 1 d . . . . .
C10 C 0.2542(5) 0.0702(4) 0.2776(3) 0.0232(7) Uani 1 1 d . . . . .
H10 H 0.295941 -0.045260 0.308663 0.028 Uiso 1 1 calc R . . . .
C11 C 0.0955(5) 0.1292(5) 0.2323(3) 0.0264(8) Uani 1 1 d . . . . .
H11 H 0.028795 0.055292 0.232143 0.032 Uiso 1 1 calc R . . . .
C12 C 0.0348(4) 0.2978(5) 0.1872(3) 0.0237(7) Uani 1 1 d . . . . .
H12 H -0.076709 0.340229 0.158728 0.028 Uiso 1 1 calc R . . . .
C13 C 0.1339(4) 0.4063(4) 0.1827(3) 0.0201(7) Uani 1 1 d . . . . .
C14 C 0.0704(4) 0.5823(4) 0.1299(3) 0.0234(7) Uani 1 1 d . . . . .
C15 C 0.2084(4) 0.6628(4) 0.0998(3) 0.0214(7) Uani 1 1 d . . . . .
C16 C 0.1820(5) 0.8030(4) 0.0189(3) 0.0236(7) Uani 1 1 d . . . . .
H16 H 0.069745 0.852179 -0.008355 0.028 Uiso 1 1 calc R . . . .
C17 C 0.3140(5) 0.8708(4) -0.0218(3) 0.0252(8) Uani 1 1 d . . . . .
H17 H 0.293865 0.967488 -0.075482 0.030 Uiso 1 1 calc R . . . .
C18 C 0.4799(5) 0.7935(4) 0.0179(3) 0.0240(7) Uani 1 1 d . . . . .
H18 H 0.574109 0.836583 -0.011589 0.029 Uiso 1 1 calc R . . . .
C19 C 0.5097(4) 0.6579(4) 0.0979(3) 0.0207(7) Uani 1 1 d . . . . .
H19 H 0.623195 0.608188 0.123486 0.025 Uiso 1 1 calc R . . . .
C20 C 0.3723(4) 0.5921(4) 0.1421(3) 0.0180(7) Uani 1 1 d . . . . .
C21 C 0.2966(4) 0.3447(4) 0.2290(3) 0.0177(7) 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
I5 C5 2.091(3) . ?
O8 C8 1.218(4) . ?
O14 C14 1.229(4) . ?
N1 C2 1.419(4) . ?
N1 C20 1.420(4) . ?
N1 C21 1.391(4) . ?
C2 C3 1.404(5) . ?
C2 C7 1.403(5) . ?
C3 C4 1.372(5) . ?
C4 C5 1.395(5) . ?
C5 C6 1.365(5) . ?
C6 C7 1.406(5) . ?
C7 C8 1.475(5) . ?
C8 C9 1.477(5) . ?
C9 C10 1.388(5) . ?
C9 C21 1.407(5) . ?
C10 C11 1.380(5) . ?
C11 C12 1.386(5) . ?
C12 C13 1.394(5) . ?
C13 C14 1.470(5) . ?
C13 C21 1.415(5) . ?
C14 C15 1.468(5) . ?
C15 C16 1.400(5) . ?
C15 C20 1.401(5) . ?
C16 C17 1.370(5) . ?
C17 C18 1.404(5) . ?
C18 C19 1.368(5) . ?
C19 C20 1.404(4) . ?

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
C2 N1 C20 122.2(3) . . ?
C21 N1 C2 119.0(3) . . ?
C21 N1 C20 118.7(3) . . ?
C3 C2 N1 121.7(3) . . ?
C7 C2 N1 118.9(3) . . ?
C7 C2 C3 119.3(3) . . ?
C4 C3 C2 120.2(3) . . ?
C3 C4 C5 120.3(3) . . ?
C4 C5 I5 120.1(2) . . ?
C6 C5 I5 119.5(2) . . ?
C6 C5 C4 120.4(3) . . ?
C5 C6 C7 120.3(3) . . ?
C2 C7 C6 119.3(3) . . ?
C2 C7 C8 121.7(3) . . ?
C6 C7 C8 118.8(3) . . ?
O8 C8 C7 123.2(3) . . ?
O8 C8 C9 122.8(3) . . ?
C7 C8 C9 113.9(3) . . ?
C10 C9 C8 120.0(3) . . ?
C10 C9 C21 119.5(3) . . ?
C21 C9 C8 120.4(3) . . ?
C11 C10 C9 121.6(3) . . ?
C10 C11 C12 119.1(3) . . ?
C11 C12 C13 121.4(3) . . ?
C12 C13 C14 120.4(3) . . ?
C12 C13 C21 119.2(3) . . ?
C21 C13 C14 120.5(3) . . ?
O14 C14 C13 122.6(3) . . ?
O14 C14 C15 122.9(3) . . ?
C15 C14 C13 114.3(3) . . ?
C16 C15 C14 119.1(3) . . ?
C16 C15 C20 119.4(3) . . ?
C20 C15 C14 121.2(3) . . ?
C17 C16 C15 121.6(3) . . ?
C16 C17 C18 118.1(3) . . ?
C19 C18 C17 121.8(3) . . ?
C18 C19 C20 119.9(3) . . ?
C15 C20 N1 119.3(3) . . ?
C15 C20 C19 119.1(3) . . ?
C19 C20 N1 121.5(3) . . ?
N1 C21 C9 120.6(3) . . ?
N1 C21 C13 120.2(3) . . ?
C9 C21 C13 119.2(3) . . ?


#===END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: chloroform/hexane'
