# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_r11319-290K
_database_code_depnum_ccdc_archive 'CCDC 1947988'
loop_
_audit_author_name
_audit_author_address
'Eric Reinheimer' 'Rigaku Americas Corporation'
_audit_update_record             
;
2019-10-04 deposited with the CCDC.	2019-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H11 N, 0.5(C6 Cl4 I2)'
_chemical_formula_sum            'C16 H11 Cl2 I N'
_chemical_formula_weight         415.06

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'
N N 0.0061 0.0033 '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                   5.7320(3)
_cell_length_b                   11.2839(6)
_cell_length_c                   12.3090(7)
_cell_angle_alpha                83.794(2)
_cell_angle_beta                 82.313(2)
_cell_angle_gamma                77.034(2)
_cell_volume                     766.35(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    3200
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      27.06

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.799
_exptl_crystal_F_000             402
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.098
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.032
_exptl_absorpt_coefficient_mu    2.426
_shelx_estimated_absorpt_T_min   0.797
_shelx_estimated_absorpt_T_max   0.926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4745
_exptl_absorpt_correction_T_max  0.5629
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 7.41
_diffrn_reflns_number            9405
_diffrn_reflns_av_unetI/netI     0.0559
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.399
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3487
_reflns_number_gt                2575
_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       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'APEX3 v2018.7--RC8 (Bruker AXS, 2018)'
_refine_special_details          
; 
  
All  H atoms were positioned geometrically and refined using a 
riding model with C---H = 0.95--0.99 Å and with Uiso(H) 
= 1.2 (1.5 for methyl groups) times Ueq(C). 
  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0211P)²+0.6222P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         3487
_refine_ls_number_parameters     188
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0370
_refine_ls_wR_factor_ref         0.0850
_refine_ls_wR_factor_gt          0.0660
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.052
_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 0.50956(5) 0.28139(3) 0.90651(3) 0.05224(12) Uani 1 1 d . . . . .
Cl1 Cl 0.3721(2) 0.57789(12) 0.81403(11) 0.0638(4) Uani 1 1 d . . . . .
Cl2 Cl 0.0773(2) 0.23520(11) 1.10945(10) 0.0586(3) Uani 1 1 d . . . . .
C14 C 0.1662(7) 0.5325(4) 0.9173(3) 0.0413(10) Uani 1 1 d . . . . .
C15 C 0.2063(7) 0.4129(4) 0.9637(3) 0.0388(10) Uani 1 1 d . . . . .
C16 C 0.0380(7) 0.3819(4) 1.0478(3) 0.0416(10) Uani 1 1 d . . . . .
N1 N -0.0992(7) 1.0943(4) 0.8157(4) 0.0596(11) Uani 1 1 d . . . . .
C1 C 0.1039(9) 1.0535(5) 0.8587(4) 0.0604(14) Uani 1 1 d . . . . .
H1 H 0.114926 1.077413 0.927509 0.072 Uiso 1 1 calc R U . . .
C2 C 0.3011(9) 0.9778(5) 0.8087(5) 0.0605(14) Uani 1 1 d . . . . .
H2 H 0.439626 0.951535 0.843869 0.073 Uiso 1 1 calc R U . . .
C3 C 0.2944(8) 0.9409(4) 0.7074(4) 0.0495(12) Uani 1 1 d D . . . .
C4 C 0.0798(9) 0.9821(5) 0.6613(4) 0.0604(14) Uani 1 1 d . . . . .
H4 H 0.063080 0.958571 0.593157 0.072 Uiso 1 1 calc R U . . .
C5 C -0.1092(9) 1.0587(5) 0.7181(5) 0.0670(15) Uani 1 1 d . . . . .
H5 H -0.251168 1.086532 0.685720 0.080 Uiso 1 1 calc R U . . .
C8 C 0.7685(8) 0.7448(4) 0.5067(4) 0.0504(12) Uani 1 1 d D . . . .
C9 C 0.9763(9) 0.6985(5) 0.5577(5) 0.0621(14) Uani 1 1 d . . . . .
H9 H 0.980613 0.715229 0.629676 0.074 Uiso 1 1 calc R U . . .
C10 C 1.1749(9) 0.6282(5) 0.5029(5) 0.0659(15) Uani 1 1 d . . . . .
H10 H 1.313042 0.597905 0.537735 0.079 Uiso 1 1 calc R U . . .
C11 C 1.1701(9) 0.6026(5) 0.3973(5) 0.0667(16) Uani 1 1 d . . . . .
H11 H 1.304670 0.554715 0.360374 0.080 Uiso 1 1 calc R U . . .
C12 C 0.9677(11) 0.6473(5) 0.3459(5) 0.0697(16) Uani 1 1 d . . . . .
H12 H 0.963690 0.629820 0.274183 0.084 Uiso 1 1 calc R U . . .
C13 C 0.7688(9) 0.7188(5) 0.4012(5) 0.0623(14) Uani 1 1 d . . . . .
H13 H 0.632167 0.749835 0.365443 0.075 Uiso 1 1 calc R U . . .
C6 C 0.5144(8) 0.8592(5) 0.6574(5) 0.0519(15) Uani 0.889(8) 1 d D . P A 1
H6 H 0.638345 0.829301 0.701227 0.062 Uiso 0.889(8) 1 calc R U P A 1
C7 C 0.5480(8) 0.8260(5) 0.5568(4) 0.0504(15) Uani 0.889(8) 1 d D . P A 1
H7 H 0.423700 0.855557 0.513166 0.061 Uiso 0.889(8) 1 calc R U P A 1
C6A C 0.413(5) 0.875(3) 0.6097(15) 0.0519(15) Uani 0.111(8) 1 d D . P A 2
H6A H 0.327986 0.883064 0.549248 0.062 Uiso 0.111(8) 1 calc R U P A 2
C7A C 0.630(5) 0.806(3) 0.6035(15) 0.0504(15) Uani 0.111(8) 1 d D . P A 2
H7A H 0.706683 0.794714 0.666947 0.061 Uiso 0.111(8) 1 calc R U P A 2


_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 C15 2.112(4) . ?
Cl1 C14 1.733(4) . ?
Cl2 C16 1.725(4) . ?
C14 C15 1.388(6) . ?
C14 C16 1.391(5) 2_567 ?
C15 C16 1.390(6) . ?
N1 C1 1.311(7) . ?
N1 C5 1.319(7) . ?
C1 C2 1.371(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.364(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.387(7) . ?
C3 C6A 1.487(4) . ?
C3 C6 1.487(4) . ?
C4 C5 1.385(7) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C8 C13 1.362(7) . ?
C8 C9 1.392(7) . ?
C8 C7 1.487(4) . ?
C8 C7A 1.487(4) . ?
C9 C10 1.373(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.367(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.365(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.382(7) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C6 C7 1.310(7) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C6A C7A 1.304(19) . ?
C6A H6A 0.9300 . ?
C7A H7A 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
C15 C14 C16 121.3(4) . 2_567 ?
C15 C14 Cl1 120.1(3) . . ?
C16 C14 Cl1 118.6(3) 2_567 . ?
C14 C15 C16 117.8(4) . . ?
C14 C15 I1 121.2(3) . . ?
C16 C15 I1 121.0(3) . . ?
C14 C16 C15 120.9(4) 2_567 . ?
C14 C16 Cl2 118.9(3) 2_567 . ?
C15 C16 Cl2 120.2(3) . . ?
C1 N1 C5 116.5(4) . . ?
N1 C1 C2 124.1(5) . . ?
N1 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
C3 C2 C1 120.2(5) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 116.4(4) . . ?
C2 C3 C6A 150.9(12) . . ?
C4 C3 C6A 92.7(12) . . ?
C2 C3 C6 117.5(5) . . ?
C4 C3 C6 126.0(5) . . ?
C5 C4 C3 119.2(5) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
N1 C5 C4 123.6(5) . . ?
N1 C5 H5 118.2 . . ?
C4 C5 H5 118.2 . . ?
C13 C8 C9 118.1(4) . . ?
C13 C8 C7 117.0(5) . . ?
C9 C8 C7 124.9(5) . . ?
C13 C8 C7A 147.0(12) . . ?
C9 C8 C7A 95.0(12) . . ?
C10 C9 C8 120.7(5) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 120.2(5) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 H10 119.9 . . ?
C10 C11 C12 120.0(5) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C13 119.7(6) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C8 C13 C12 121.5(5) . . ?
C8 C13 H13 119.3 . . ?
C12 C13 H13 119.3 . . ?
C7 C6 C3 125.4(5) . . ?
C7 C6 H6 117.3 . . ?
C3 C6 H6 117.3 . . ?
C6 C7 C8 125.4(5) . . ?
C6 C7 H7 117.3 . . ?
C8 C7 H7 117.3 . . ?
C7A C6A C3 124.2(14) . . ?
C7A C6A H6A 117.9 . . ?
C3 C6A H6A 117.9 . . ?
C6A C7A C8 127.6(16) . . ?
C6A C7A H7A 116.2 . . ?
C8 C7A H7A 116.2 . . ?

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
C16 C14 C15 C16 -1.3(7) 2_567 . . . ?
Cl1 C14 C15 C16 178.7(3) . . . . ?
C16 C14 C15 I1 177.6(3) 2_567 . . . ?
Cl1 C14 C15 I1 -2.4(5) . . . . ?
C14 C15 C16 C14 1.3(7) . . . 2_567 ?
I1 C15 C16 C14 -177.6(3) . . . 2_567 ?
C14 C15 C16 Cl2 -179.7(3) . . . . ?
I1 C15 C16 Cl2 1.3(5) . . . . ?
C5 N1 C1 C2 0.1(8) . . . . ?
N1 C1 C2 C3 0.5(9) . . . . ?
C1 C2 C3 C4 -1.2(8) . . . . ?
C1 C2 C3 C6A 176(3) . . . . ?
C1 C2 C3 C6 179.8(5) . . . . ?
C2 C3 C4 C5 1.4(8) . . . . ?
C6A C3 C4 C5 -177.1(15) . . . . ?
C6 C3 C4 C5 -179.7(5) . . . . ?
C1 N1 C5 C4 0.2(8) . . . . ?
C3 C4 C5 N1 -1.0(9) . . . . ?
C13 C8 C9 C10 -0.2(8) . . . . ?
C7 C8 C9 C10 -177.3(5) . . . . ?
C7A C8 C9 C10 179.2(17) . . . . ?
C8 C9 C10 C11 -0.2(9) . . . . ?
C9 C10 C11 C12 0.2(9) . . . . ?
C10 C11 C12 C13 0.3(9) . . . . ?
C9 C8 C13 C12 0.7(8) . . . . ?
C7 C8 C13 C12 178.0(5) . . . . ?
C7A C8 C13 C12 -178(3) . . . . ?
C11 C12 C13 C8 -0.8(9) . . . . ?
C2 C3 C6 C7 -172.3(6) . . . . ?
C4 C3 C6 C7 8.8(9) . . . . ?
C3 C6 C7 C8 179.6(5) . . . . ?
C13 C8 C7 C6 179.0(6) . . . . ?
C9 C8 C7 C6 -4.0(9) . . . . ?
C2 C3 C6A C7A 7(6) . . . . ?
C4 C3 C6A C7A -176(4) . . . . ?
C3 C6A C7A C8 -175(3) . . . . ?
C13 C8 C7A C6A -4(6) . . . . ?
C9 C8 C7A C6A 176(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1 Cl2 0.93 2.97 3.854(6) 160.4 1_565 yes

_refine_diff_density_max         0.624
_refine_diff_density_min         -0.515
_refine_diff_density_rms         0.105

####################################################################### 
# 
# 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_r3919-mo-100k
_database_code_depnum_ccdc_archive 'CCDC 1947991'
loop_
_audit_author_name
_audit_author_address
'Eric Reinheimer' 'Rigaku Americas Corporation'
_audit_update_record             
;
2019-10-04 deposited with the CCDC.	2019-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H11 N, 0.5(C6 Cl4 I2)'
_chemical_formula_sum            'C16 H11 Cl2 I N'
_chemical_formula_weight         415.06

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'
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      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                   5.6832(2)
_cell_length_b                   11.0865(4)
_cell_length_c                   12.2076(5)
_cell_angle_alpha                82.9822(14)
_cell_angle_beta                 82.3948(12)
_cell_angle_gamma                77.3857(12)
_cell_volume                     740.53(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9976
_cell_measurement_theta_min      3.38
_cell_measurement_theta_max      26.43

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.861
_exptl_crystal_F_000             402
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.375
_exptl_crystal_size_mid          0.264
_exptl_crystal_size_min          0.159
_exptl_absorpt_coefficient_mu    2.511
_shelx_estimated_absorpt_T_min   0.453
_shelx_estimated_absorpt_T_max   0.691
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4031
_exptl_absorpt_correction_T_max  0.4908
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 7.41
_diffrn_reflns_number            12920
_diffrn_reflns_av_unetI/netI     0.0162
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.412
_diffrn_reflns_theta_max         26.427
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2996
_reflns_number_gt                2941
_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       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'APEX3 v2018.7--RC8 (Bruker AXS, 2018)'
_refine_special_details          
; 
  
All  H atoms were positioned geometrically and refined using a 
riding model with C---H = 0.95--0.99 Å and with Uiso(H) 
= 1.2 (1.5 for methyl groups) times Ueq(C). 
  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0149P)²+0.9729P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         2996
_refine_ls_number_parameters     214
_refine_ls_number_restraints     33
_refine_ls_R_factor_all          0.0162
_refine_ls_R_factor_gt           0.0157
_refine_ls_wR_factor_ref         0.0390
_refine_ls_wR_factor_gt          0.0387
_refine_ls_goodness_of_fit_ref   0.985
_refine_ls_restrained_S_all      0.990
_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 0.51526(2) 0.28080(2) 0.90722(2) 0.01884(5) Uani 1 1 d . . . . .
Cl1 Cl 0.37372(9) 0.58370(5) 0.81174(4) 0.02274(10) Uani 1 1 d . . . . .
Cl2 Cl -0.08140(9) 0.77031(4) 0.88716(4) 0.02187(10) Uani 1 1 d . . . . .
C14 C 0.2101(3) 0.41271(17) 0.96424(15) 0.0159(4) Uani 1 1 d . . . . .
C15 C 0.1677(3) 0.53508(17) 0.91592(15) 0.0158(4) Uani 1 1 d . . . . .
C16 C -0.0395(3) 0.62041(17) 0.95058(15) 0.0159(4) Uani 1 1 d . . . . .
N1 N -0.0997(4) 1.0976(2) 0.81569(19) 0.0235(5) Uani 0.918(3) 1 d D . P A 1
C1 C 0.1066(5) 1.0567(3) 0.8617(2) 0.0228(5) Uani 0.918(3) 1 d D . P A 1
H1 H 0.115773 1.081284 0.932574 0.027 Uiso 0.918(3) 1 calc R U P A 1
C2 C 0.3081(4) 0.9805(2) 0.8120(2) 0.0221(5) Uani 0.918(3) 1 d D . P A 1
H2 H 0.450612 0.954641 0.848763 0.026 Uiso 0.918(3) 1 calc R U P A 1
C3 C 0.3029(4) 0.9415(2) 0.70852(19) 0.0184(5) Uani 0.918(3) 1 d D . P A 1
C4 C 0.0851(5) 0.9842(2) 0.6605(2) 0.0223(6) Uani 0.918(3) 1 d D . P A 1
H4 H 0.069952 0.960919 0.589790 0.027 Uiso 0.918(3) 1 calc R U P A 1
C5 C -0.1065(5) 1.0600(3) 0.7160(2) 0.0261(6) Uani 0.918(3) 1 d D . P A 1
H5 H -0.252081 1.087344 0.681704 0.031 Uiso 0.918(3) 1 calc R U P A 1
C6 C 0.5174(4) 0.86007(19) 0.65746(18) 0.0190(4) Uani 0.918(3) 1 d D . P A 1
H6 H 0.646708 0.828460 0.701793 0.023 Uiso 0.918(3) 1 calc R U P A 1
C7 C 0.5481(4) 0.82606(19) 0.55442(18) 0.0189(4) Uani 0.918(3) 1 d D . P A 1
H7 H 0.417804 0.856225 0.510398 0.023 Uiso 0.918(3) 1 calc R U P A 1
C8 C 0.7665(4) 0.7458(2) 0.50294(18) 0.0186(5) Uani 0.918(3) 1 d D . P A 1
C9 C 0.9767(5) 0.7009(2) 0.55575(18) 0.0201(5) Uani 0.918(3) 1 d D . P A 1
H9 H 0.981222 0.720170 0.629075 0.024 Uiso 0.918(3) 1 calc R U P A 1
C10 C 1.1784(4) 0.6286(2) 0.5017(2) 0.0230(5) Uani 0.918(3) 1 d D . P A 1
H10 H 1.320250 0.598428 0.538351 0.028 Uiso 0.918(3) 1 calc R U P A 1
C11 C 1.1748(5) 0.5998(3) 0.3946(2) 0.0243(6) Uani 0.918(3) 1 d D . P A 1
H11 H 1.314387 0.551118 0.357619 0.029 Uiso 0.918(3) 1 calc R U P A 1
C12 C 0.9670(6) 0.6423(5) 0.3419(3) 0.0237(8) Uani 0.918(3) 1 d D . P A 1
H12 H 0.963174 0.621935 0.268904 0.028 Uiso 0.918(3) 1 calc R U P A 1
C13 C 0.7645(8) 0.7146(4) 0.3954(3) 0.0216(6) Uani 0.918(3) 1 d D . P A 1
H13 H 0.622510 0.743292 0.358672 0.026 Uiso 0.918(3) 1 calc R U P A 1
N1A N -0.089(4) 1.068(3) 0.8414(19) 0.0235(5) Uani 0.082(3) 1 d DG . P A -2
C1A C 0.150(5) 1.047(3) 0.8662(15) 0.0228(5) Uani 0.082(3) 1 d DG . P A -2
H1A H 0.182360 1.059590 0.937868 0.027 Uiso 0.082(3) 1 calc R U P A -2
C2A C 0.340(4) 1.008(3) 0.7863(17) 0.0221(5) Uani 0.082(3) 1 d DG . P A -2
H2A H 0.502706 0.993018 0.803303 0.026 Uiso 0.082(3) 1 calc R U P A -2
C3A C 0.292(3) 0.989(2) 0.6815(15) 0.0184(5) Uani 0.082(3) 1 d DG . P A -2
C4A C 0.054(4) 1.010(3) 0.6566(18) 0.0223(6) Uani 0.082(3) 1 d DG . P A -2
H4A H 0.021115 0.997829 0.585018 0.027 Uiso 0.082(3) 1 calc R U P A -2
C5A C -0.136(3) 1.050(3) 0.737(2) 0.0261(6) Uani 0.082(3) 1 d DG . P A -2
H5A H -0.299235 1.064400 0.719582 0.031 Uiso 0.082(3) 1 calc R U P A -2
C6A C 0.497(4) 0.977(2) 0.5895(15) 0.0190(4) Uani 0.082(3) 1 d D . P A -2
H6A H 0.624933 1.019501 0.589884 0.023 Uiso 0.082(3) 1 calc R U P A -2
C7A C 0.504(4) 0.9018(19) 0.5016(17) 0.0189(4) Uani 0.082(3) 1 d D . P A -2
H7A H 0.379762 0.922296 0.453472 0.023 Uiso 0.082(3) 1 calc R U P A -2
C8A C 0.705(4) 0.791(2) 0.484(2) 0.0186(5) Uani 0.082(3) 1 d D . P A -2
C9A C 0.897(4) 0.751(3) 0.546(2) 0.0201(5) Uani 0.082(3) 1 d D . P A -2
H9A H 0.887937 0.788074 0.612932 0.024 Uiso 0.082(3) 1 calc R U P A -2
C10A C 1.101(5) 0.664(3) 0.520(3) 0.0230(5) Uani 0.082(3) 1 d D . P A -2
H10A H 1.224740 0.642633 0.568426 0.028 Uiso 0.082(3) 1 calc R U P A -2
C11A C 1.125(6) 0.608(4) 0.422(3) 0.0243(6) Uani 0.082(3) 1 d D . P A -2
H11A H 1.265672 0.548341 0.400214 0.029 Uiso 0.082(3) 1 calc R U P A -2
C12A C 0.930(8) 0.644(6) 0.359(4) 0.0237(8) Uani 0.082(3) 1 d D . P A -2
H12A H 0.936826 0.603569 0.293548 0.028 Uiso 0.082(3) 1 calc R U P A -2
C13A C 0.729(9) 0.734(5) 0.385(4) 0.0216(6) Uani 0.082(3) 1 d D . P A -2
H13A H 0.605592 0.758212 0.336236 0.026 Uiso 0.082(3) 1 calc R U P A -2


_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 C14 2.1101(18) . ?
Cl1 C15 1.7298(19) . ?
Cl2 C16 1.7261(19) . ?
C14 C15 1.395(3) . ?
C14 C16 1.397(3) 2_567 ?
C15 C16 1.393(3) . ?
N1 C1 1.332(3) . ?
N1 C5 1.341(3) . ?
C1 C2 1.382(3) . ?
C1 H1 0.9500 . ?
C2 C3 1.390(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.403(3) . ?
C3 C6 1.465(3) . ?
C4 C5 1.377(3) . ?
C4 H4 0.9500 . ?
C5 H5 0.9500 . ?
C6 C7 1.336(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.475(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.399(3) . ?
C8 C13 1.400(3) . ?
C9 C10 1.386(3) . ?
C9 H9 0.9500 . ?
C10 C11 1.387(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.384(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.385(3) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
N1A C1A 1.3900 . ?
N1A C5A 1.3900 . ?
C1A C2A 1.3900 . ?
C1A H1A 0.9500 . ?
C2A C3A 1.3900 . ?
C2A H2A 0.9500 . ?
C3A C4A 1.3900 . ?
C3A C6A 1.505(15) . ?
C4A C5A 1.3900 . ?
C4A H4A 0.9500 . ?
C5A H5A 0.9500 . ?
C6A C7A 1.427(17) . ?
C6A H6A 0.9500 . ?
C7A C8A 1.498(17) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.369(17) . ?
C8A C13A 1.414(17) . ?
C9A C10A 1.361(18) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.394(18) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.396(18) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.378(18) . ?
C12A H12A 0.9500 . ?
C13A H13A 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
C15 C14 C16 117.66(17) . 2_567 ?
C15 C14 I1 121.17(13) . . ?
C16 C14 I1 121.14(14) 2_567 . ?
C16 C15 C14 120.94(17) . . ?
C16 C15 Cl1 118.75(14) . . ?
C14 C15 Cl1 120.30(14) . . ?
C15 C16 C14 121.39(17) . 2_567 ?
C15 C16 Cl2 118.63(14) . . ?
C14 C16 Cl2 119.98(14) 2_567 . ?
C1 N1 C5 116.43(19) . . ?
N1 C1 C2 123.7(2) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C1 C2 C3 120.2(2) . . ?
C1 C2 H2 119.9 . . ?
C3 C2 H2 119.9 . . ?
C2 C3 C4 116.0(2) . . ?
C2 C3 C6 119.5(2) . . ?
C4 C3 C6 124.5(2) . . ?
C5 C4 C3 119.8(2) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
N1 C5 C4 123.8(2) . . ?
N1 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
C7 C6 C3 126.1(2) . . ?
C7 C6 H6 116.9 . . ?
C3 C6 H6 116.9 . . ?
C6 C7 C8 125.8(2) . . ?
C6 C7 H7 117.1 . . ?
C8 C7 H7 117.1 . . ?
C9 C8 C13 118.4(2) . . ?
C9 C8 C7 123.2(2) . . ?
C13 C8 C7 118.4(2) . . ?
C10 C9 C8 120.4(2) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C9 C10 C11 120.5(2) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 119.7(2) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 120.1(2) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C8 120.8(2) . . ?
C12 C13 H13 119.6 . . ?
C8 C13 H13 119.6 . . ?
C1A N1A C5A 120.0 . . ?
C2A C1A N1A 120.0 . . ?
C2A C1A H1A 120.0 . . ?
N1A C1A H1A 120.0 . . ?
C3A C2A C1A 120.0 . . ?
C3A C2A H2A 120.0 . . ?
C1A C2A H2A 120.0 . . ?
C2A C3A C4A 120.0 . . ?
C2A C3A C6A 118.5(14) . . ?
C4A C3A C6A 119.9(14) . . ?
C3A C4A C5A 120.0 . . ?
C3A C4A H4A 120.0 . . ?
C5A C4A H4A 120.0 . . ?
C4A C5A N1A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
N1A C5A H5A 120.0 . . ?
C7A C6A C3A 121.2(17) . . ?
C7A C6A H6A 119.4 . . ?
C3A C6A H6A 119.4 . . ?
C6A C7A C8A 120.6(17) . . ?
C6A C7A H7A 119.7 . . ?
C8A C7A H7A 119.7 . . ?
C9A C8A C13A 114.5(17) . . ?
C9A C8A C7A 126.2(18) . . ?
C13A C8A C7A 118.1(19) . . ?
C10A C9A C8A 126.6(19) . . ?
C10A C9A H9A 116.7 . . ?
C8A C9A H9A 116.7 . . ?
C9A C10A C11A 119(2) . . ?
C9A C10A H10A 120.4 . . ?
C11A C10A H10A 120.4 . . ?
C10A C11A C12A 116(2) . . ?
C10A C11A H11A 122.0 . . ?
C12A C11A H11A 122.0 . . ?
C13A C12A C11A 124(2) . . ?
C13A C12A H12A 118.1 . . ?
C11A C12A H12A 118.1 . . ?
C12A C13A C8A 120(2) . . ?
C12A C13A H13A 120.1 . . ?
C8A C13A H13A 120.1 . . ?

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
C16 C14 C15 C16 -0.9(3) 2_567 . . . ?
I1 C14 C15 C16 177.14(13) . . . . ?
C16 C14 C15 Cl1 178.80(14) 2_567 . . . ?
I1 C14 C15 Cl1 -3.1(2) . . . . ?
C14 C15 C16 C14 1.0(3) . . . 2_567 ?
Cl1 C15 C16 C14 -178.77(14) . . . 2_567 ?
C14 C15 C16 Cl2 -179.86(14) . . . . ?
Cl1 C15 C16 Cl2 0.4(2) . . . . ?
C5 N1 C1 C2 0.6(4) . . . . ?
N1 C1 C2 C3 -0.3(5) . . . . ?
C1 C2 C3 C4 0.0(4) . . . . ?
C1 C2 C3 C6 -179.6(3) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C6 C3 C4 C5 179.6(2) . . . . ?
C1 N1 C5 C4 -0.5(4) . . . . ?
C3 C4 C5 N1 0.3(4) . . . . ?
C2 C3 C6 C7 -172.5(2) . . . . ?
C4 C3 C6 C7 8.0(4) . . . . ?
C3 C6 C7 C8 178.8(2) . . . . ?
C6 C7 C8 C9 -3.8(4) . . . . ?
C6 C7 C8 C13 177.1(3) . . . . ?
C13 C8 C9 C10 0.8(4) . . . . ?
C7 C8 C9 C10 -178.3(2) . . . . ?
C8 C9 C10 C11 0.1(4) . . . . ?
C9 C10 C11 C12 -0.9(5) . . . . ?
C10 C11 C12 C13 0.8(7) . . . . ?
C11 C12 C13 C8 0.1(8) . . . . ?
C9 C8 C13 C12 -0.9(6) . . . . ?
C7 C8 C13 C12 178.2(4) . . . . ?
C5A N1A C1A C2A 0.0 . . . . ?
N1A C1A C2A C3A 0.0 . . . . ?
C1A C2A C3A C4A 0.0 . . . . ?
C1A C2A C3A C6A 165(2) . . . . ?
C2A C3A C4A C5A 0.0 . . . . ?
C6A C3A C4A C5A -165(2) . . . . ?
C3A C4A C5A N1A 0.0 . . . . ?
C1A N1A C5A C4A 0.0 . . . . ?
C2A C3A C6A C7A 149(2) . . . . ?
C4A C3A C6A C7A -46(3) . . . . ?
C3A C6A C7A C8A -118(3) . . . . ?
C6A C7A C8A C9A -1(4) . . . . ?
C6A C7A C8A C13A -168(4) . . . . ?
C13A C8A C9A C10A 0(6) . . . . ?
C7A C8A C9A C10A -168(3) . . . . ?
C8A C9A C10A C11A 0(5) . . . . ?
C9A C10A C11A C12A -2(6) . . . . ?
C10A C11A C12A C13A 3(10) . . . . ?
C11A C12A C13A C8A -4(12) . . . . ?
C9A C8A C13A C12A 2(9) . . . . ?
C7A C8A C13A C12A 171(6) . . . . ?

_refine_diff_density_max         0.809
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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_r11319-250K
_database_code_depnum_ccdc_archive 'CCDC 1947989'
loop_
_audit_author_name
_audit_author_address
'Eric Reinheimer' 'Rigaku Americas Corporation'
_audit_update_record             
;
2019-10-04 deposited with the CCDC.	2019-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H11 N, 0.5(C6 Cl4 I2)'
_chemical_formula_sum            'C16 H11 Cl2 I N'
_chemical_formula_weight         415.06

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'
N N 0.0061 0.0033 '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                   5.7219(2)
_cell_length_b                   11.2301(4)
_cell_length_c                   12.2908(4)
_cell_angle_alpha                83.6745(16)
_cell_angle_beta                 82.3392(14)
_cell_angle_gamma                77.1630(14)
_cell_volume                     760.51(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    3585
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      27.46

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.813
_exptl_crystal_F_000             402
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.098
_exptl_crystal_size_mid          0.089
_exptl_crystal_size_min          0.032
_exptl_absorpt_coefficient_mu    2.445
_shelx_estimated_absorpt_T_min   0.796
_shelx_estimated_absorpt_T_max   0.926
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4923
_exptl_absorpt_correction_T_max  0.5629
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      250(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 7.41
_diffrn_reflns_number            9468
_diffrn_reflns_av_unetI/netI     0.0522
_diffrn_reflns_av_R_equivalents  0.0434
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.404
_diffrn_reflns_theta_max         27.510
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             3477
_reflns_number_gt                2794
_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       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'APEX3 v2018.7--RC8 (Bruker AXS, 2018)'
_refine_special_details          
; 
  
All  H atoms were positioned geometrically and refined using a 
riding model with C---H = 0.95--0.99 Å and with Uiso(H) 
= 1.2 (1.5 for methyl groups) times Ueq(C). 
  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0186P)²+0.8226P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         3477
_refine_ls_number_parameters     188
_refine_ls_number_restraints     11
_refine_ls_R_factor_all          0.0539
_refine_ls_R_factor_gt           0.0361
_refine_ls_wR_factor_ref         0.0796
_refine_ls_wR_factor_gt          0.0646
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.059
_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 0.51063(5) 0.28136(3) 0.90618(2) 0.04384(11) Uani 1 1 d . . . . .
Cl1 Cl 0.3720(2) 0.57948(11) 0.81348(10) 0.0542(3) Uani 1 1 d . . . . .
Cl2 Cl 0.0787(2) 0.23381(10) 1.10997(9) 0.0494(3) Uani 1 1 d . . . . .
C14 C 0.1665(7) 0.5330(4) 0.9168(3) 0.0360(9) Uani 1 1 d . . . . .
C15 C 0.2085(7) 0.4125(4) 0.9638(3) 0.0343(9) Uani 1 1 d . . . . .
C16 C 0.0383(7) 0.3821(4) 1.0480(3) 0.0340(9) Uani 1 1 d . . . . .
N1 N -0.1004(6) 1.0951(4) 0.8153(3) 0.0503(10) Uani 1 1 d . . . . .
C1 C 0.1030(8) 1.0550(5) 0.8585(4) 0.0514(12) Uani 1 1 d . . . . .
H1 H 0.112866 1.080056 0.927896 0.062 Uiso 1 1 calc R U . . .
C2 C 0.3029(8) 0.9790(4) 0.8100(4) 0.0504(12) Uani 1 1 d . . . . .
H2 H 0.442709 0.953305 0.846108 0.060 Uiso 1 1 calc R U . . .
C3 C 0.2962(7) 0.9407(4) 0.7072(4) 0.0429(10) Uani 1 1 d D . . . .
C4 C 0.0827(8) 0.9821(4) 0.6609(4) 0.0497(11) Uani 1 1 d . . . . .
H4 H 0.066992 0.958655 0.591546 0.060 Uiso 1 1 calc R U . . .
C5 C -0.1070(8) 1.0579(5) 0.7169(4) 0.0554(13) Uani 1 1 d . . . . .
H5 H -0.250200 1.085075 0.683509 0.066 Uiso 1 1 calc R U . . .
C8 C 0.7675(7) 0.7457(4) 0.5055(4) 0.0429(11) Uani 1 1 d D . . . .
C9 C 0.9752(8) 0.6988(4) 0.5571(4) 0.0490(11) Uani 1 1 d . . . . .
H9 H 0.979395 0.715481 0.630008 0.059 Uiso 1 1 calc R U . . .
C10 C 1.1746(8) 0.6280(5) 0.5020(5) 0.0571(13) Uani 1 1 d . . . . .
H10 H 1.313911 0.597031 0.537566 0.069 Uiso 1 1 calc R U . . .
C11 C 1.1714(9) 0.6027(5) 0.3965(5) 0.0580(14) Uani 1 1 d . . . . .
H11 H 1.308872 0.555328 0.359151 0.070 Uiso 1 1 calc R U . . .
C12 C 0.9678(10) 0.6462(5) 0.3448(4) 0.0594(14) Uani 1 1 d . . . . .
H12 H 0.964370 0.627384 0.272473 0.071 Uiso 1 1 calc R U . . .
C13 C 0.7671(8) 0.7180(4) 0.3990(4) 0.0517(12) Uani 1 1 d . . . . .
H13 H 0.628585 0.748212 0.362655 0.062 Uiso 1 1 calc R U . . .
C6 C 0.5140(7) 0.8588(4) 0.6574(4) 0.0434(13) Uani 0.919(7) 1 d D . P A 1
H6 H 0.638717 0.827558 0.701978 0.052 Uiso 0.919(7) 1 calc R U P A 1
C7 C 0.5482(7) 0.8259(4) 0.5561(4) 0.0415(12) Uani 0.919(7) 1 d D . P A 1
H7 H 0.422258 0.856107 0.512001 0.050 Uiso 0.919(7) 1 calc R U P A 1
C6A C 0.414(6) 0.880(3) 0.6074(15) 0.0434(13) Uani 0.081(7) 1 d D . P A 2
H6A H 0.332403 0.895243 0.544263 0.052 Uiso 0.081(7) 1 calc R U P A 2
C7A C 0.628(6) 0.806(3) 0.6020(16) 0.0415(12) Uani 0.081(7) 1 d D . P A 2
H7A H 0.701640 0.789688 0.667578 0.050 Uiso 0.081(7) 1 calc R U P A 2


_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 C15 2.105(4) . ?
Cl1 C14 1.731(4) . ?
Cl2 C16 1.733(4) . ?
C14 C15 1.394(6) . ?
C14 C16 1.389(5) 2_567 ?
C15 C16 1.391(5) . ?
N1 C1 1.311(6) . ?
N1 C5 1.330(6) . ?
C1 C2 1.374(6) . ?
C1 H1 0.9400 . ?
C2 C3 1.387(6) . ?
C2 H2 0.9400 . ?
C3 C4 1.381(6) . ?
C3 C6 1.478(4) . ?
C3 C6A 1.478(4) . ?
C4 C5 1.377(6) . ?
C4 H4 0.9400 . ?
C5 H5 0.9400 . ?
C8 C13 1.380(7) . ?
C8 C9 1.393(6) . ?
C8 C7A 1.478(4) . ?
C8 C7 1.478(4) . ?
C9 C10 1.379(6) . ?
C9 H9 0.9400 . ?
C10 C11 1.361(7) . ?
C10 H10 0.9400 . ?
C11 C12 1.370(7) . ?
C11 H11 0.9400 . ?
C12 C13 1.383(6) . ?
C12 H12 0.9400 . ?
C13 H13 0.9400 . ?
C6 C7 1.315(6) . ?
C6 H6 0.9400 . ?
C7 H7 0.9400 . ?
C6A C7A 1.315(19) . ?
C6A H6A 0.9400 . ?
C7A H7A 0.9400 . ?

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
C15 C14 C16 121.1(4) . 2_567 ?
C15 C14 Cl1 120.1(3) . . ?
C16 C14 Cl1 118.8(3) 2_567 . ?
C14 C15 C16 117.1(3) . . ?
C14 C15 I1 121.3(3) . . ?
C16 C15 I1 121.6(3) . . ?
C14 C16 C15 121.9(4) 2_567 . ?
C14 C16 Cl2 118.6(3) 2_567 . ?
C15 C16 Cl2 119.5(3) . . ?
C1 N1 C5 115.7(4) . . ?
N1 C1 C2 125.0(5) . . ?
N1 C1 H1 117.5 . . ?
C2 C1 H1 117.5 . . ?
C1 C2 C3 119.2(4) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C4 C3 C2 116.4(4) . . ?
C4 C3 C6 125.7(4) . . ?
C2 C3 C6 117.9(4) . . ?
C4 C3 C6A 91.7(13) . . ?
C2 C3 C6A 151.6(14) . . ?
C5 C4 C3 119.6(4) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
N1 C5 C4 124.1(4) . . ?
N1 C5 H5 117.9 . . ?
C4 C5 H5 117.9 . . ?
C13 C8 C9 118.1(4) . . ?
C13 C8 C7A 146.8(14) . . ?
C9 C8 C7A 95.1(13) . . ?
C13 C8 C7 117.4(4) . . ?
C9 C8 C7 124.5(4) . . ?
C10 C9 C8 120.5(5) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C11 C10 C9 120.5(5) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C10 C11 C12 119.9(4) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C13 120.1(5) . . ?
C11 C12 H12 120.0 . . ?
C13 C12 H12 120.0 . . ?
C8 C13 C12 120.9(5) . . ?
C8 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C7 C6 C3 125.6(4) . . ?
C7 C6 H6 117.2 . . ?
C3 C6 H6 117.2 . . ?
C6 C7 C8 125.7(4) . . ?
C6 C7 H7 117.1 . . ?
C8 C7 H7 117.1 . . ?
C7A C6A C3 123.6(15) . . ?
C7A C6A H6A 118.2 . . ?
C3 C6A H6A 118.2 . . ?
C6A C7A C8 128.1(17) . . ?
C6A C7A H7A 116.0 . . ?
C8 C7A H7A 116.0 . . ?

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
C16 C14 C15 C16 -0.8(7) 2_567 . . . ?
Cl1 C14 C15 C16 178.7(3) . . . . ?
C16 C14 C15 I1 177.3(3) 2_567 . . . ?
Cl1 C14 C15 I1 -3.2(5) . . . . ?
C14 C15 C16 C14 0.8(7) . . . 2_567 ?
I1 C15 C16 C14 -177.3(3) . . . 2_567 ?
C14 C15 C16 Cl2 179.8(3) . . . . ?
I1 C15 C16 Cl2 1.8(5) . . . . ?
C5 N1 C1 C2 -0.2(7) . . . . ?
N1 C1 C2 C3 0.5(8) . . . . ?
C1 C2 C3 C4 -0.6(7) . . . . ?
C1 C2 C3 C6 -179.9(4) . . . . ?
C1 C2 C3 C6A 171(4) . . . . ?
C2 C3 C4 C5 0.5(7) . . . . ?
C6 C3 C4 C5 179.7(4) . . . . ?
C6A C3 C4 C5 -175.3(17) . . . . ?
C1 N1 C5 C4 0.1(7) . . . . ?
C3 C4 C5 N1 -0.2(8) . . . . ?
C13 C8 C9 C10 0.8(7) . . . . ?
C7A C8 C9 C10 178.8(19) . . . . ?
C7 C8 C9 C10 -177.7(4) . . . . ?
C8 C9 C10 C11 -0.2(8) . . . . ?
C9 C10 C11 C12 -0.9(8) . . . . ?
C10 C11 C12 C13 1.3(8) . . . . ?
C9 C8 C13 C12 -0.4(7) . . . . ?
C7A C8 C13 C12 -177(3) . . . . ?
C7 C8 C13 C12 178.2(4) . . . . ?
C11 C12 C13 C8 -0.7(8) . . . . ?
C4 C3 C6 C7 9.3(8) . . . . ?
C2 C3 C6 C7 -171.5(5) . . . . ?
C3 C6 C7 C8 178.9(4) . . . . ?
C13 C8 C7 C6 177.9(5) . . . . ?
C9 C8 C7 C6 -3.7(8) . . . . ?
C4 C3 C6A C7A -171(4) . . . . ?
C2 C3 C6A C7A 17(7) . . . . ?
C3 C6A C7A C8 -177(3) . . . . ?
C13 C8 C7A C6A -10(7) . . . . ?
C9 C8 C7A C6A 173(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C1 H1 Cl2 0.94 2.93 3.839(5) 161.8 1_565 yes

_refine_diff_density_max         0.477
_refine_diff_density_min         -0.558
_refine_diff_density_rms         0.109

####################################################################### 
# 
# 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_r9719-290K
_database_code_depnum_ccdc_archive 'CCDC 1947992'
loop_
_audit_author_name
_audit_author_address
'Eric Reinheimer' 'Rigaku Americas Corporation'
_audit_update_record             
;
2019-10-09 deposited with the CCDC.	2019-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H11 N, 0.5(C6 Cl4 I2)'
_chemical_formula_sum            'C16 H11 Cl2 I N'
_chemical_formula_weight         415.06

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'
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                   10.9466(5)
_cell_length_b                   16.4851(7)
_cell_length_c                   8.6575(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.0062(19)
_cell_angle_gamma                90
_cell_volume                     1553.72(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    9991
_cell_measurement_theta_min      2.47
_cell_measurement_theta_max      30.41

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.774
_exptl_crystal_F_000             804
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.156
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.122
_exptl_absorpt_coefficient_mu    2.393
_shelx_estimated_absorpt_T_min   0.707
_shelx_estimated_absorpt_T_max   0.759
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7181
_exptl_absorpt_correction_T_max  0.8374
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 7.41
_diffrn_reflns_number            43120
_diffrn_reflns_av_unetI/netI     0.0843
_diffrn_reflns_av_R_equivalents  0.0970
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.242
_diffrn_reflns_theta_max         30.539
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4692
_reflns_number_gt                2904
_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       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'APEX3 v2018.7--RC8 (Bruker AXS, 2018)'
_refine_special_details          
; 
  
All  H atoms were positioned geometrically and refined using a 
riding model with C---H = 0.95--0.99 Å and with Uiso(H) 
= 1.2 (1.5 for methyl groups) times Ueq(C). 
  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0210P)²+0.9087P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         4692
_refine_ls_number_parameters     210
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.1405
_refine_ls_R_factor_gt           0.0662
_refine_ls_wR_factor_ref         0.0794
_refine_ls_wR_factor_gt          0.0704
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.084
_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
Cl1 Cl 0.95601(9) 0.31356(6) -0.00722(12) 0.0655(3) Uani 0.9749(13) 1 d D . P .
.
I1 I 0.82795(2) 0.41173(2) 0.27687(3) 0.06064(10) Uani 1 1 d D . . A 1
Cl2 Cl 0.90528(11) 0.60805(7) 0.25557(15) 0.0720(3) Uani 0.9749(13) 1 d D . P B
1
I2 I 0.8914(9) 0.5727(9) 0.3346(13) 0.077(6) Uani 0.0251(13) 1 d D . P B 2
C14 C 0.9788(3) 0.41717(19) -0.0025(4) 0.0466(7) Uani 1 1 d D . . . .
C15 C 0.9332(3) 0.4642(2) 0.1122(3) 0.0467(7) Uani 1 1 d D . . . .
C16 C 0.9562(3) 0.54690(19) 0.1139(3) 0.0464(7) Uani 1 1 d D . . . .
N1 N 0.6686(3) 0.35249(18) 0.5051(4) 0.0631(8) Uani 1 1 d . . . . .
C1 C 0.7063(4) 0.3199(2) 0.6410(5) 0.0653(10) Uani 1 1 d . . . . .
H1 H 0.781884 0.293572 0.651659 0.078 Uiso 1 1 calc R U . . .
C2 C 0.6409(4) 0.3227(2) 0.7668(5) 0.0716(11) Uani 1 1 d . . . . .
H2 H 0.671399 0.297994 0.859515 0.086 Uiso 1 1 calc R U . . .
C3 C 0.5297(4) 0.3621(3) 0.7558(5) 0.0710(12) Uani 1 1 d D . . . .
C4 C 0.4903(3) 0.3952(2) 0.6157(6) 0.0729(12) Uani 1 1 d . . . . .
H4 H 0.415439 0.422284 0.601962 0.087 Uiso 1 1 calc R U . . .
C5 C 0.5607(4) 0.3888(2) 0.4950(5) 0.0662(10) Uani 1 1 d . . . . .
H5 H 0.530797 0.411418 0.400047 0.079 Uiso 1 1 calc R U . . .
C6 C 0.4422(6) 0.3909(4) 0.8676(8) 0.0490(17) Uani 0.518(4) 1 d D . P C 1
H6 H 0.395353 0.437456 0.847307 0.059 Uiso 0.518(4) 1 calc R U P C 1
C7 C 0.4339(6) 0.3482(4) 0.9948(8) 0.0502(17) Uani 0.518(4) 1 d D . P C 1
H7 H 0.480606 0.301565 1.015286 0.060 Uiso 0.518(4) 1 calc R U P C 1
C6' C 0.4808(7) 0.3446(5) 0.9116(8) 0.062(2) Uani 0.518(4) 1 d D . P C 2
H6' H 0.505550 0.298945 0.969753 0.075 Uiso 0.518(4) 1 calc R U P C 2
C7' C 0.4031(7) 0.3963(5) 0.9596(8) 0.0585(19) Uani 0.518(4) 1 d D . P C 2
H7' H 0.383410 0.443670 0.904323 0.070 Uiso 0.518(4) 1 calc R U P C 2
C8 C 0.3450(3) 0.3777(3) 1.1076(4) 0.0658(10) Uani 1 1 d D . . . .
C9 C 0.3095(3) 0.3109(2) 1.1857(5) 0.0691(10) Uani 1 1 d . . . . .
H9 H 0.334092 0.259535 1.156997 0.083 Uiso 1 1 calc R U . . .
C10 C 0.2384(4) 0.3189(3) 1.3055(5) 0.0741(11) Uani 1 1 d . . . . .
H10 H 0.215302 0.273231 1.358462 0.089 Uiso 1 1 calc R U . . .
C11 C 0.2011(3) 0.3947(3) 1.3472(4) 0.0740(12) Uani 1 1 d . . . . .
H11 H 0.151809 0.400485 1.427709 0.089 Uiso 1 1 calc R U . . .
C12 C 0.2364(4) 0.4606(3) 1.2711(5) 0.0741(11) Uani 1 1 d . . . . .
H12 H 0.212430 0.511904 1.300735 0.089 Uiso 1 1 calc R U . . .
C13 C 0.3062(4) 0.4527(3) 1.1520(5) 0.0720(11) Uani 1 1 d . . . . .
H13 H 0.328388 0.498682 1.099384 0.086 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
Cl1 C14 1.726(3) . ?
I1 C15 2.110(3) . ?
Cl2 C16 1.725(3) . ?
I2 C16 2.149(8) . ?
C14 C16 1.389(4) 3_765 ?
C14 C15 1.393(4) . ?
C15 C16 1.386(4) . ?
N1 C5 1.319(5) . ?
N1 C1 1.319(5) . ?
C1 C2 1.366(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.374(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.359(6) . ?
C3 C6 1.508(6) . ?
C3 C6' 1.531(7) . ?
C4 C5 1.366(6) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C7 1.318(7) . ?
C6 H6 0.9300 . ?
C7 C8 1.528(6) . ?
C7 H7 0.9300 . ?
C6' C7' 1.302(7) . ?
C6' H6' 0.9300 . ?
C7' C8 1.520(7) . ?
C7' H7' 0.9300 . ?
C8 C9 1.369(5) . ?
C8 C13 1.375(6) . ?
C9 C10 1.366(5) . ?
C9 H9 0.9300 . ?
C10 C11 1.375(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.347(6) . ?
C11 H11 0.9300 . ?
C12 C13 1.353(6) . ?
C12 H12 0.9300 . ?
C13 H13 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
C16 C14 C15 120.4(3) 3_765 . ?
C16 C14 Cl1 119.3(2) 3_765 . ?
C15 C14 Cl1 120.4(2) . . ?
C16 C15 C14 118.4(2) . . ?
C16 C15 I1 120.5(2) . . ?
C14 C15 I1 121.0(2) . . ?
C15 C16 C14 121.2(3) . 3_765 ?
C15 C16 Cl2 120.7(2) . . ?
C14 C16 Cl2 118.1(2) 3_765 . ?
C15 C16 I2 97.3(5) . . ?
C14 C16 I2 140.6(5) 3_765 . ?
C5 N1 C1 116.0(3) . . ?
N1 C1 C2 123.8(4) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C1 C2 C3 119.6(4) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 116.7(3) . . ?
C4 C3 C6 106.4(4) . . ?
C2 C3 C6 136.2(5) . . ?
C4 C3 C6' 139.0(5) . . ?
C2 C3 C6' 103.8(5) . . ?
C3 C4 C5 120.0(4) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
N1 C5 C4 123.9(4) . . ?
N1 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
C7 C6 C3 118.2(5) . . ?
C7 C6 H6 120.9 . . ?
C3 C6 H6 120.9 . . ?
C6 C7 C8 117.9(5) . . ?
C6 C7 H7 121.0 . . ?
C8 C7 H7 121.0 . . ?
C7' C6' C3 117.3(6) . . ?
C7' C6' H6' 121.3 . . ?
C3 C6' H6' 121.3 . . ?
C6' C7' C8 118.8(6) . . ?
C6' C7' H7' 120.6 . . ?
C8 C7' H7' 120.6 . . ?
C9 C8 C13 118.2(3) . . ?
C9 C8 C7' 138.1(4) . . ?
C13 C8 C7' 102.9(4) . . ?
C9 C8 C7 107.0(4) . . ?
C13 C8 C7 134.5(4) . . ?
C10 C9 C8 120.7(4) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C9 C10 C11 119.7(4) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C12 C11 C10 119.7(3) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 120.6(4) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C12 C13 C8 121.0(4) . . ?
C12 C13 H13 119.5 . . ?
C8 C13 H13 119.5 . . ?

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
C16 C14 C15 C16 -1.2(5) 3_765 . . . ?
Cl1 C14 C15 C16 178.4(2) . . . . ?
C16 C14 C15 I1 177.4(2) 3_765 . . . ?
Cl1 C14 C15 I1 -2.9(4) . . . . ?
C14 C15 C16 C14 1.2(5) . . . 3_765 ?
I1 C15 C16 C14 -177.4(2) . . . 3_765 ?
C14 C15 C16 Cl2 -178.5(2) . . . . ?
I1 C15 C16 Cl2 2.9(4) . . . . ?
C14 C15 C16 I2 -170.3(4) . . . . ?
C5 N1 C1 C2 -0.4(6) . . . . ?
N1 C1 C2 C3 -0.9(6) . . . . ?
C1 C2 C3 C4 1.3(6) . . . . ?
C1 C2 C3 C6 -167.3(5) . . . . ?
C1 C2 C3 C6' 174.6(4) . . . . ?
C2 C3 C4 C5 -0.4(6) . . . . ?
C6 C3 C4 C5 171.4(4) . . . . ?
C6' C3 C4 C5 -170.5(6) . . . . ?
C1 N1 C5 C4 1.3(5) . . . . ?
C3 C4 C5 N1 -0.9(6) . . . . ?
C4 C3 C6 C7 158.0(6) . . . . ?
C2 C3 C6 C7 -32.7(9) . . . . ?
C3 C6 C7 C8 180.0(5) . . . . ?
C4 C3 C6' C7' -34.2(11) . . . . ?
C2 C3 C6' C7' 154.9(6) . . . . ?
C3 C6' C7' C8 175.4(5) . . . . ?
C6' C7' C8 C9 -31.8(11) . . . . ?
C6' C7' C8 C13 159.6(6) . . . . ?
C6 C7 C8 C9 153.0(6) . . . . ?
C6 C7 C8 C13 -33.8(9) . . . . ?
C13 C8 C9 C10 -0.6(6) . . . . ?
C7' C8 C9 C10 -167.9(6) . . . . ?
C7 C8 C9 C10 173.9(4) . . . . ?
C8 C9 C10 C11 0.5(6) . . . . ?
C9 C10 C11 C12 -0.9(6) . . . . ?
C10 C11 C12 C13 1.2(6) . . . . ?
C11 C12 C13 C8 -1.3(6) . . . . ?
C9 C8 C13 C12 0.9(6) . . . . ?
C7' C8 C13 C12 172.3(4) . . . . ?
C7 C8 C13 C12 -171.7(5) . . . . ?

_refine_diff_density_max         0.448
_refine_diff_density_min         -0.636
_refine_diff_density_rms         0.068

####################################################################### 
# 
# 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_r9719-250K
_database_code_depnum_ccdc_archive 'CCDC 1947993'
loop_
_audit_author_name
_audit_author_address
'Eric Reinheimer' 'Rigaku Americas Corporation'
_audit_update_record             
;
2019-10-04 deposited with the CCDC.	2019-10-14 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H11 N, 0.5(C6 Cl4 I2)'
_chemical_formula_sum            'C16 H11 Cl2 I N'
_chemical_formula_weight         415.06

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'
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                   10.9007(3)
_cell_length_b                   16.4319(4)
_cell_length_c                   8.6457(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.2379(10)
_cell_angle_gamma                90
_cell_volume                     1539.44(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    250(2)
_cell_measurement_reflns_used    9938
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      30.43

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.791
_exptl_crystal_F_000             804
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.156
_exptl_crystal_size_mid          0.155
_exptl_crystal_size_min          0.122
_exptl_absorpt_coefficient_mu    2.416
_shelx_estimated_absorpt_T_min   0.704
_shelx_estimated_absorpt_T_max   0.757
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7419
_exptl_absorpt_correction_T_max  0.8374
_exptl_absorpt_process_details   'SADABS V2016/2 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      250(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 7.41
_diffrn_reflns_number            29690
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.251
_diffrn_reflns_theta_max         30.521
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             4634
_reflns_number_gt                3491
_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       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'APEX3 v2018.7--RC8 (Bruker AXS, 2018)'
_refine_special_details          
; 
  
All  H atoms were positioned geometrically and refined using a 
riding model with C---H = 0.95--0.99 Å and with Uiso(H) 
= 1.2 (1.5 for methyl groups) times Ueq(C). 
  
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0133P)²+1.4949P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         4634
_refine_ls_number_parameters     210
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0554
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0762
_refine_ls_wR_factor_gt          0.0638
_refine_ls_goodness_of_fit_ref   1.141
_refine_ls_restrained_S_all      1.145
_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
Cl1 Cl 0.95609(8) 0.31293(5) -0.00723(11) 0.0556(2) Uani 0.9770(12) 1 d D . P .
.
I1 I 0.82774(2) 0.41138(2) 0.27706(2) 0.05149(8) Uani 1 1 d D . . A 1
Cl2 Cl 0.90512(10) 0.60837(6) 0.25591(14) 0.0606(2) Uani 0.9770(12) 1 d D . P B
1
I2 I 0.8923(8) 0.5721(8) 0.3367(11) 0.058(5) Uani 0.0230(12) 1 d D . P B 2
C14 C 0.9786(3) 0.41687(17) -0.0026(3) 0.0404(6) Uani 1 1 d D . . . .
C15 C 0.9331(3) 0.46382(19) 0.1119(3) 0.0411(6) Uani 1 1 d D . . . .
C16 C 0.9561(3) 0.54724(18) 0.1139(3) 0.0405(6) Uani 1 1 d D . . . .
N1 N 0.6690(3) 0.35243(17) 0.5047(3) 0.0539(7) Uani 1 1 d . . . . .
C1 C 0.7072(3) 0.31936(19) 0.6418(4) 0.0563(8) Uani 1 1 d . . . . .
H1 H 0.783435 0.292110 0.653100 0.068 Uiso 1 1 calc R U . . .
C2 C 0.6409(4) 0.3230(2) 0.7675(4) 0.0624(9) Uani 1 1 d . . . . .
H2 H 0.671592 0.298499 0.862044 0.075 Uiso 1 1 calc R U . . .
C3 C 0.5288(3) 0.3628(3) 0.7546(5) 0.0655(11) Uani 1 1 d D . . . .
C4 C 0.4895(3) 0.3957(2) 0.6136(5) 0.0650(10) Uani 1 1 d . . . . .
H4 H 0.413521 0.423236 0.598868 0.078 Uiso 1 1 calc R U . . .
C5 C 0.5603(4) 0.3889(2) 0.4932(4) 0.0590(9) Uani 1 1 d . . . . .
H5 H 0.530025 0.411442 0.396601 0.071 Uiso 1 1 calc R U . . .
C6 C 0.4411(5) 0.3913(3) 0.8669(6) 0.0389(12) Uani 0.523(4) 1 d D . P C 1
H6 H 0.393931 0.438808 0.847733 0.047 Uiso 0.523(4) 1 calc R U P C 1
C7 C 0.4329(5) 0.3470(3) 0.9938(6) 0.0405(13) Uani 0.523(4) 1 d D . P C 1
H7 H 0.479605 0.299227 1.012905 0.049 Uiso 0.523(4) 1 calc R U P C 1
C6' C 0.4803(6) 0.3443(4) 0.9116(8) 0.0560(17) Uani 0.523(4) 1 d D . P C 2
H6' H 0.505880 0.297948 0.970137 0.067 Uiso 0.523(4) 1 calc R U P C 2
C7' C 0.4025(6) 0.3958(4) 0.9592(8) 0.0541(16) Uani 0.523(4) 1 d D . P C 2
H7' H 0.382258 0.443911 0.903287 0.065 Uiso 0.523(4) 1 calc R U P C 2
C8 C 0.3445(3) 0.3767(3) 1.1075(4) 0.0608(10) Uani 1 1 d D . . . .
C9 C 0.3088(3) 0.3098(2) 1.1868(5) 0.0616(9) Uani 1 1 d . . . . .
H9 H 0.334159 0.257608 1.159218 0.074 Uiso 1 1 calc R U . . .
C10 C 0.2370(4) 0.3185(3) 1.3051(4) 0.0645(10) Uani 1 1 d . . . . .
H10 H 0.211959 0.272471 1.358071 0.077 Uiso 1 1 calc R U . . .
C11 C 0.2008(3) 0.3955(3) 1.3471(4) 0.0648(10) Uani 1 1 d . . . . .
H11 H 0.151203 0.401789 1.428719 0.078 Uiso 1 1 calc R U . . .
C12 C 0.2368(4) 0.4615(2) 1.2710(5) 0.0648(10) Uani 1 1 d . . . . .
H12 H 0.213206 0.513706 1.300683 0.078 Uiso 1 1 calc R U . . .
C13 C 0.3071(4) 0.4527(2) 1.1515(4) 0.0643(10) Uani 1 1 d . . . . .
H13 H 0.330587 0.499044 1.098119 0.077 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
Cl1 C14 1.725(3) . ?
I1 C15 2.111(3) . ?
Cl2 C16 1.724(3) . ?
I2 C16 2.157(7) . ?
C14 C15 1.389(4) . ?
C14 C16 1.389(4) 3_765 ?
C15 C16 1.393(4) . ?
N1 C5 1.322(5) . ?
N1 C1 1.329(5) . ?
C1 C2 1.370(5) . ?
C1 H1 0.9400 . ?
C2 C3 1.380(6) . ?
C2 H2 0.9400 . ?
C3 C4 1.360(6) . ?
C3 C6 1.509(6) . ?
C3 C6' 1.540(7) . ?
C4 C5 1.366(6) . ?
C4 H4 0.9400 . ?
C5 H5 0.9400 . ?
C6 C7 1.327(6) . ?
C6 H6 0.9400 . ?
C7 C8 1.530(6) . ?
C7 H7 0.9400 . ?
C6' C7' 1.296(7) . ?
C6' H6' 0.9400 . ?
C7' C8 1.523(7) . ?
C7' H7' 0.9400 . ?
C8 C9 1.374(5) . ?
C8 C13 1.381(6) . ?
C9 C10 1.362(5) . ?
C9 H9 0.9400 . ?
C10 C11 1.385(6) . ?
C10 H10 0.9400 . ?
C11 C12 1.348(6) . ?
C11 H11 0.9400 . ?
C12 C13 1.359(6) . ?
C12 H12 0.9400 . ?
C13 H13 0.9400 . ?

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
C15 C14 C16 120.5(3) . 3_765 ?
C15 C14 Cl1 120.4(2) . . ?
C16 C14 Cl1 119.1(2) 3_765 . ?
C14 C15 C16 118.5(2) . . ?
C14 C15 I1 121.2(2) . . ?
C16 C15 I1 120.2(2) . . ?
C14 C16 C15 121.0(2) 3_765 . ?
C14 C16 Cl2 118.4(2) 3_765 . ?
C15 C16 Cl2 120.7(2) . . ?
C14 C16 I2 141.0(4) 3_765 . ?
C15 C16 I2 97.0(4) . . ?
C5 N1 C1 116.3(3) . . ?
N1 C1 C2 123.3(3) . . ?
N1 C1 H1 118.4 . . ?
C2 C1 H1 118.4 . . ?
C1 C2 C3 119.7(4) . . ?
C1 C2 H2 120.2 . . ?
C3 C2 H2 120.2 . . ?
C4 C3 C2 116.8(3) . . ?
C4 C3 C6 107.1(4) . . ?
C2 C3 C6 135.4(4) . . ?
C4 C3 C6' 139.8(4) . . ?
C2 C3 C6' 102.8(4) . . ?
C3 C4 C5 120.1(4) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
N1 C5 C4 123.8(4) . . ?
N1 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
C7 C6 C3 117.8(5) . . ?
C7 C6 H6 121.1 . . ?
C3 C6 H6 121.1 . . ?
C6 C7 C8 117.4(5) . . ?
C6 C7 H7 121.3 . . ?
C8 C7 H7 121.3 . . ?
C7' C6' C3 116.7(6) . . ?
C7' C6' H6' 121.6 . . ?
C3 C6' H6' 121.6 . . ?
C6' C7' C8 118.5(6) . . ?
C6' C7' H7' 120.7 . . ?
C8 C7' H7' 120.7 . . ?
C9 C8 C13 118.6(3) . . ?
C9 C8 C7' 138.7(4) . . ?
C13 C8 C7' 101.9(4) . . ?
C9 C8 C7 107.4(4) . . ?
C13 C8 C7 133.7(4) . . ?
C10 C9 C8 120.6(3) . . ?
C10 C9 H9 119.7 . . ?
C8 C9 H9 119.7 . . ?
C9 C10 C11 119.7(4) . . ?
C9 C10 H10 120.1 . . ?
C11 C10 H10 120.1 . . ?
C12 C11 C10 120.0(3) . . ?
C12 C11 H11 120.0 . . ?
C10 C11 H11 120.0 . . ?
C11 C12 C13 120.3(4) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C12 C13 C8 120.9(4) . . ?
C12 C13 H13 119.6 . . ?
C8 C13 H13 119.6 . . ?

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
C16 C14 C15 C16 -0.9(5) 3_765 . . . ?
Cl1 C14 C15 C16 178.3(2) . . . . ?
C16 C14 C15 I1 177.7(2) 3_765 . . . ?
Cl1 C14 C15 I1 -3.1(3) . . . . ?
C14 C15 C16 C14 0.9(5) . . . 3_765 ?
I1 C15 C16 C14 -177.7(2) . . . 3_765 ?
C14 C15 C16 Cl2 -178.5(2) . . . . ?
I1 C15 C16 Cl2 2.9(3) . . . . ?
C14 C15 C16 I2 -169.9(3) . . . . ?
C5 N1 C1 C2 -1.1(5) . . . . ?
N1 C1 C2 C3 -0.2(6) . . . . ?
C1 C2 C3 C4 1.0(5) . . . . ?
C1 C2 C3 C6 -168.1(4) . . . . ?
C1 C2 C3 C6' 173.9(4) . . . . ?
C2 C3 C4 C5 -0.3(5) . . . . ?
C6 C3 C4 C5 171.7(4) . . . . ?
C6' C3 C4 C5 -169.6(5) . . . . ?
C1 N1 C5 C4 1.8(5) . . . . ?
C3 C4 C5 N1 -1.1(6) . . . . ?
C4 C3 C6 C7 157.1(5) . . . . ?
C2 C3 C6 C7 -33.1(8) . . . . ?
C3 C6 C7 C8 179.6(4) . . . . ?
C4 C3 C6' C7' -34.9(10) . . . . ?
C2 C3 C6' C7' 154.9(6) . . . . ?
C3 C6' C7' C8 175.4(5) . . . . ?
C6' C7' C8 C9 -31.9(10) . . . . ?
C6' C7' C8 C13 159.0(6) . . . . ?
C6 C7 C8 C9 154.0(5) . . . . ?
C6 C7 C8 C13 -32.9(8) . . . . ?
C13 C8 C9 C10 0.7(6) . . . . ?
C7' C8 C9 C10 -167.2(5) . . . . ?
C7 C8 C9 C10 175.0(4) . . . . ?
C8 C9 C10 C11 -0.8(6) . . . . ?
C9 C10 C11 C12 0.0(6) . . . . ?
C10 C11 C12 C13 0.9(6) . . . . ?
C11 C12 C13 C8 -1.0(6) . . . . ?
C9 C8 C13 C12 0.2(6) . . . . ?
C7' C8 C13 C12 172.1(4) . . . . ?
C7 C8 C13 C12 -172.2(4) . . . . ?

_refine_diff_density_max         0.512
_refine_diff_density_min         -0.582
_refine_diff_density_rms         0.087

