# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_dd18319_0m
_audit_block_doi                 10.5517/ccdc.csd.cc226drg
_database_code_depnum_ccdc_archive 'CCDC 1912785'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1016/j.chempr.2020.03.011 2020
loop_
_audit_author_name
_audit_author_address
'Bo Xu'
;Donghua University
China
;
_audit_update_record             
;
2019-07-23 deposited with the CCDC.	2022-10-17 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H10 Cl I'
_chemical_formula_weight         340.57

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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.7863(4)
_cell_length_b                   9.7114(3)
_cell_length_c                   13.7154(5)
_cell_angle_alpha                90
_cell_angle_beta                 100.442(2)
_cell_angle_gamma                90
_cell_volume                     1281.91(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3567
_cell_measurement_theta_min      5.169
_cell_measurement_theta_max      54.844

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.765
_exptl_crystal_F_000             656
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    2.676
_shelx_estimated_absorpt_T_min   0.659
_shelx_estimated_absorpt_T_max   0.757
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5529
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6080
_diffrn_reflns_av_unetI/netI     0.0250
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.116
_diffrn_reflns_theta_max         25.988
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             2478
_reflns_number_gt                2109
_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       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0383P)²+2.3172P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0055(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2478
_refine_ls_number_parameters     146
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0397
_refine_ls_wR_factor_ref         0.1017
_refine_ls_wR_factor_gt          0.0956
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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
I1 I 0.75372(4) 1.01969(4) 0.33024(3) 0.0781(2) Uani 1 1 d . . . . .
Cl1 Cl 0.82030(13) 0.73047(13) 0.07223(8) 0.0633(3) Uani 1 1 d . . . . .
C1 C 0.7781(4) 0.9237(5) 0.1995(3) 0.0550(10) Uani 1 1 d . . . . .
H1 H 0.7840 0.9793 0.1453 0.066 Uiso 1 1 calc R U . . .
C2 C 0.7857(4) 0.7890(4) 0.1879(3) 0.0467(9) Uani 1 1 d . . . . .
C3 C 0.7684(4) 0.6774(4) 0.2581(3) 0.0434(8) Uani 1 1 d . . . . .
C4 C 0.6471(4) 0.6649(4) 0.2952(3) 0.0506(9) Uani 1 1 d . . . . .
H4 H 0.5761 0.7286 0.2768 0.061 Uiso 1 1 calc R U . . .
C5 C 0.6295(4) 0.5596(4) 0.3591(3) 0.0493(9) Uani 1 1 d . . . . .
H5 H 0.5463 0.5528 0.3825 0.059 Uiso 1 1 calc R U . . .
C6 C 0.7339(4) 0.4628(4) 0.3894(3) 0.0411(8) Uani 1 1 d . . . . .
C7 C 0.8554(4) 0.4758(4) 0.3504(3) 0.0482(9) Uani 1 1 d . . . . .
H7 H 0.9267 0.4124 0.3683 0.058 Uiso 1 1 calc R U . . .
C8 C 0.8719(4) 0.5803(4) 0.2862(3) 0.0479(9) Uani 1 1 d . . . . .
H8 H 0.9539 0.5861 0.2610 0.057 Uiso 1 1 calc R U . . .
C9 C 0.7159(4) 0.3508(4) 0.4593(3) 0.0425(8) Uani 1 1 d . . . . .
C10 C 0.5864(4) 0.2960(4) 0.4629(3) 0.0524(10) Uani 1 1 d . . . . .
H10 H 0.5089 0.3298 0.4202 0.063 Uiso 1 1 calc R U . . .
C11 C 0.5697(5) 0.1921(5) 0.5286(4) 0.0630(12) Uani 1 1 d . . . . .
H11 H 0.4817 0.1566 0.5295 0.076 Uiso 1 1 calc R U . . .
C12 C 0.6827(5) 0.1410(5) 0.5927(4) 0.0685(13) Uani 1 1 d . . . . .
H12 H 0.6716 0.0720 0.6377 0.082 Uiso 1 1 calc R U . . .
C13 C 0.8114(5) 0.1929(5) 0.5894(4) 0.0689(13) Uani 1 1 d . . . . .
H13 H 0.8883 0.1578 0.6320 0.083 Uiso 1 1 calc R U . . .
C14 C 0.8298(4) 0.2968(4) 0.5239(3) 0.0528(10) Uani 1 1 d . . . . .
H14 H 0.9184 0.3307 0.5230 0.063 Uiso 1 1 calc R U . . .


_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 2.072(5) . ?
Cl1 C2 1.774(4) . ?
C1 C2 1.322(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.480(5) . ?
C3 C4 1.379(5) . ?
C3 C8 1.387(5) . ?
C4 C5 1.378(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.396(6) . ?
C6 C9 1.481(5) . ?
C7 C8 1.372(6) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 C10 1.383(6) . ?
C9 C14 1.394(5) . ?
C10 C11 1.382(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.375(7) . ?
C11 H11 0.9300 . ?
C12 C13 1.365(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.384(6) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?

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 C1 I1 124.6(3) . . ?
C2 C1 H1 117.7 . . ?
I1 C1 H1 117.7 . . ?
C1 C2 C3 129.1(4) . . ?
C1 C2 Cl1 116.7(3) . . ?
C3 C2 Cl1 114.2(3) . . ?
C4 C3 C8 118.2(4) . . ?
C4 C3 C2 120.8(3) . . ?
C8 C3 C2 121.0(3) . . ?
C5 C4 C3 121.0(4) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C4 C5 C6 121.4(4) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C7 C6 C5 117.0(4) . . ?
C7 C6 C9 121.6(3) . . ?
C5 C6 C9 121.4(3) . . ?
C8 C7 C6 121.4(4) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C3 121.1(4) . . ?
C7 C8 H8 119.5 . . ?
C3 C8 H8 119.5 . . ?
C10 C9 C14 117.7(4) . . ?
C10 C9 C6 121.5(3) . . ?
C14 C9 C6 120.8(3) . . ?
C11 C10 C9 121.4(4) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C12 C11 C10 120.3(4) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C11 119.0(4) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C12 C13 C14 121.4(4) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 H13 119.3 . . ?
C13 C14 C9 120.2(4) . . ?
C13 C14 H14 119.9 . . ?
C9 C14 H14 119.9 . . ?

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
I1 C1 C2 C3 5.3(7) . . . . ?
I1 C1 C2 Cl1 -175.2(2) . . . . ?
C1 C2 C3 C4 58.2(6) . . . . ?
Cl1 C2 C3 C4 -121.4(4) . . . . ?
C1 C2 C3 C8 -123.7(5) . . . . ?
Cl1 C2 C3 C8 56.7(4) . . . . ?
C8 C3 C4 C5 0.6(6) . . . . ?
C2 C3 C4 C5 178.7(4) . . . . ?
C3 C4 C5 C6 0.7(7) . . . . ?
C4 C5 C6 C7 -1.4(6) . . . . ?
C4 C5 C6 C9 179.0(4) . . . . ?
C5 C6 C7 C8 0.9(6) . . . . ?
C9 C6 C7 C8 -179.6(4) . . . . ?
C6 C7 C8 C3 0.4(6) . . . . ?
C4 C3 C8 C7 -1.1(6) . . . . ?
C2 C3 C8 C7 -179.2(4) . . . . ?
C7 C6 C9 C10 -149.3(4) . . . . ?
C5 C6 C9 C10 30.2(5) . . . . ?
C7 C6 C9 C14 30.6(5) . . . . ?
C5 C6 C9 C14 -149.9(4) . . . . ?
C14 C9 C10 C11 0.5(6) . . . . ?
C6 C9 C10 C11 -179.6(4) . . . . ?
C9 C10 C11 C12 0.3(7) . . . . ?
C10 C11 C12 C13 -1.0(8) . . . . ?
C11 C12 C13 C14 0.9(8) . . . . ?
C12 C13 C14 C9 -0.1(7) . . . . ?
C10 C9 C14 C13 -0.6(6) . . . . ?
C6 C9 C14 C13 179.5(4) . . . . ?

_refine_diff_density_max         1.069
_refine_diff_density_min         -0.788
_refine_diff_density_rms         0.069

_shelxl_version_number           2013-4

