# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 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_spi-023
_audit_block_doi                 10.5517/ccdc.csd.cc1ldjr8
_database_code_depnum_ccdc_archive 'CCDC 1471810'
_audit_update_record             
;
2016-04-01 deposited with the CCDC.	2020-01-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
4-IODO-1-(4-METHOXYPHENYL)-2-(4-NITROPHENYL)-1H-PYRROLE-3-CARBADEHYDE
_chemical_name_common            ?
_chemical_melting_point          481K
_chemical_formula_moiety         'C17 H10 Cl I N2 O3 S0'
_chemical_formula_sum            'C17 H10 Cl I N2 O3 S0'
_chemical_formula_weight         452.62

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'
S S 0.1246 0.1234 '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'

_symmetry_cell_setting           ORTHORHOMBIC
_symmetry_space_group_name_H-M   Pca21
_symmetry_space_group_name_HALL  'P 2C -2ac'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -y, z'

_cell_length_a                   18.4757(12)
_cell_length_b                   9.7925(5)
_cell_length_c                   18.6956(13)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3382.5(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2042
_cell_measurement_theta_min      3.7160
_cell_measurement_theta_max      27.3100

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            WHITE
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.778
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1760
_exptl_absorpt_coefficient_mu    2.069
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.39569
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.40 (release 27-08-2010 CrysAlis171 .NET)
(compiled Aug 27 2010,11:50:40)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 16.1049
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            8495
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_sigmaI/netI    0.0518
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.73
_diffrn_reflns_theta_max         25.99
_reflns_number_total             5369
_reflns_number_gt                3531
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro,Oxford Diff.Ltd,Ver 1.171.34.40'
_computing_cell_refinement       'CrysAlisPro,Oxford Diff.Ltd,Ver 1.171.34.40'
_computing_data_reduction        'CrysAlisPro,Oxford Diff.Ltd,Ver 1.171.34.40'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 1997)'
_computing_publication_material  'PLATON(Spek,2009)& PARST(Nardelli,1995)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0494P)²+0.3410P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.72(4)
_refine_ls_number_reflns         5369
_refine_ls_number_parameters     441
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0804
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1215
_refine_ls_wR_factor_gt          0.0987
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.028
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
I1A I 0.88032(4) 0.36949(7) 0.26787(3) 0.0769(3) Uani 1 1 d . . .
N1A N 0.8960(3) 0.7952(7) 0.3050(4) 0.0418(16) Uani 1 1 d . . .
N2A N 0.6272(4) 1.2408(8) 0.2937(5) 0.062(2) Uani 1 1 d . . .
O1A O 0.7139(3) 0.4975(7) 0.2449(5) 0.085(3) Uani 1 1 d . . .
O2A O 0.6177(4) 1.2977(10) 0.3519(5) 0.097(3) Uani 1 1 d . . .
O3A O 0.5936(3) 1.2676(8) 0.2404(4) 0.087(2) Uani 1 1 d . . .
Cl1A Cl 1.08131(16) 1.2800(4) 0.3372(2) 0.1142(13) Uani 1 1 d . . .
C1A C 0.8688(4) 0.5800(10) 0.2811(6) 0.051(3) Uani 1 1 d . . .
C2A C 0.8047(4) 0.6582(8) 0.2706(5) 0.0456(19) Uani 1 1 d . . .
C3A C 0.8241(4) 0.7947(8) 0.2864(4) 0.045(2) Uani 1 1 d . . .
C4A C 0.9217(5) 0.6623(10) 0.3018(5) 0.054(2) Uani 1 1 d . . .
C5A C 0.7779(4) 0.9159(8) 0.2873(4) 0.044(2) Uani 1 1 d . . .
C6A C 0.7397(4) 0.9575(11) 0.2261(5) 0.056(2) Uani 1 1 d . . .
H6A H 0.7477 0.9130 0.1828 0.067 Uiso 1 1 calc R . .
C7A C 0.6905(4) 1.0629(10) 0.2291(5) 0.058(2) Uani 1 1 d . . .
H7A H 0.6634 1.0862 0.1890 0.070 Uiso 1 1 calc R . .
C8A C 0.6821(4) 1.1321(8) 0.2911(5) 0.049(2) Uani 1 1 d . . .
C9A C 0.7192(5) 1.0980(10) 0.3511(5) 0.058(2) Uani 1 1 d . . .
H9A H 0.7121 1.1472 0.3931 0.069 Uiso 1 1 calc R . .
C10A C 0.7681(5) 0.9887(9) 0.3498(6) 0.057(3) Uani 1 1 d . . .
H10A H 0.7938 0.9653 0.3908 0.068 Uiso 1 1 calc R . .
C11A C 0.9403(4) 0.9140(9) 0.3139(4) 0.044(2) Uani 1 1 d . . .
C12A C 0.9582(5) 0.9873(9) 0.2553(5) 0.054(3) Uani 1 1 d . . .
H12A H 0.9404 0.9624 0.2107 0.064 Uiso 1 1 calc R . .
C13A C 1.0039(4) 1.1016(10) 0.2619(5) 0.059(2) Uani 1 1 d . . .
H13A H 1.0173 1.1515 0.2217 0.071 Uiso 1 1 calc R . .
C14A C 1.0279(4) 1.1374(10) 0.3269(7) 0.064(3) Uani 1 1 d . . .
C15A C 1.0098(5) 1.0594(12) 0.3874(6) 0.079(3) Uani 1 1 d . . .
H15A H 1.0278 1.0827 0.4323 0.095 Uiso 1 1 calc R . .
C16A C 0.9657(5) 0.9495(12) 0.3795(5) 0.073(3) Uani 1 1 d . . .
H16A H 0.9528 0.8982 0.4194 0.087 Uiso 1 1 calc R . .
C17A C 0.7323(4) 0.6136(10) 0.2534(5) 0.055(2) Uani 1 1 d . . .
H17A H 0.6969 0.6806 0.2485 0.066 Uiso 1 1 calc R . .
I1B I 0.87439(4) 1.13690(6) 0.06343(3) 0.0772(3) Uani 1 1 d . . .
Cl1B Cl 0.66036(15) 0.2398(3) -0.0096(2) 0.1089(12) Uani 1 1 d . . .
O1B O 1.0386(3) 1.0052(7) 0.0923(5) 0.082(3) Uani 1 1 d . . .
O2B O 1.1378(3) 0.2125(7) -0.0002(5) 0.0722(19) Uani 1 1 d . . .
O3B O 1.1569(3) 0.2394(7) 0.1119(4) 0.086(2) Uani 1 1 d . . .
N1B N 0.8545(3) 0.7098(7) 0.0370(4) 0.0457(17) Uani 1 1 d . . .
N2B N 1.1255(3) 0.2680(7) 0.0564(5) 0.0579(18) Uani 1 1 d . . .
C1B C 0.8836(4) 0.9261(9) 0.0569(6) 0.047(2) Uani 1 1 d . . .
C4B C 0.8299(5) 0.8452(10) 0.0357(4) 0.048(2) Uani 1 1 d . . .
C3B C 0.9248(3) 0.7086(8) 0.0584(4) 0.0370(17) Uani 1 1 d . . .
C2B C 0.9451(4) 0.8443(8) 0.0690(4) 0.0416(18) Uani 1 1 d . . .
C5B C 0.9709(4) 0.5856(9) 0.0598(5) 0.0422(18) Uani 1 1 d . . .
C6B C 1.0109(4) 0.5542(10) 0.1209(4) 0.048(2) Uani 1 1 d . . .
H6B H 1.0046 0.6055 0.1623 0.057 Uiso 1 1 calc R . .
C7B C 1.0596(4) 0.4481(9) 0.1204(4) 0.051(2) Uani 1 1 d . . .
H7B H 1.0856 0.4265 0.1614 0.061 Uiso 1 1 calc R . .
C8B C 1.0695(3) 0.3746(7) 0.0589(5) 0.0426(18) Uani 1 1 d . . .
C9B C 1.0294(5) 0.4011(9) -0.0023(5) 0.054(2) Uani 1 1 d . . .
H9B H 1.0357 0.3490 -0.0434 0.065 Uiso 1 1 calc R . .
C10B C 0.9800(5) 0.5067(9) -0.0005(5) 0.053(2) Uani 1 1 d . . .
H10B H 0.9523 0.5250 -0.0409 0.063 Uiso 1 1 calc R . .
C11B C 0.8088(4) 0.5935(9) 0.0242(4) 0.046(2) Uani 1 1 d . . .
C12B C 0.7803(5) 0.5727(12) -0.0424(5) 0.074(3) Uani 1 1 d . . .
H12B H 0.7910 0.6307 -0.0804 0.088 Uiso 1 1 calc R . .
C13B C 0.7343(5) 0.4597(12) -0.0508(6) 0.082(4) Uani 1 1 d . . .
H13B H 0.7156 0.4406 -0.0959 0.098 Uiso 1 1 calc R . .
C14B C 0.7168(4) 0.3797(10) 0.0036(6) 0.058(3) Uani 1 1 d . . .
C15B C 0.7442(5) 0.4027(9) 0.0715(6) 0.061(2) Uani 1 1 d . . .
H15B H 0.7315 0.3467 0.1097 0.073 Uiso 1 1 calc R . .
C16B C 0.7911(4) 0.5116(9) 0.0807(5) 0.052(3) Uani 1 1 d . . .
H16B H 0.8106 0.5292 0.1257 0.063 Uiso 1 1 calc R . .
C17B C 1.0196(4) 0.8885(10) 0.0872(5) 0.059(2) Uani 1 1 d . . .
H17B H 1.0540 0.8209 0.0952 0.071 Uiso 1 1 calc R . .
H4B H 0.772(3) 0.857(7) 0.023(4) 0.039(19) Uiso 1 1 d . . .
H4A H 0.970(4) 0.650(8) 0.311(4) 0.05(2) Uiso 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
I1A C1A 2.087(9) . ?
N1A C3A 1.373(9) . ?
N1A C4A 1.386(11) . ?
N1A C11A 1.432(10) . ?
N2A O3A 1.203(9) . ?
N2A O2A 1.236(11) . ?
N2A C8A 1.471(10) . ?
O1A C17A 1.196(10) . ?
Cl1A C14A 1.720(9) . ?
C1A C4A 1.323(13) . ?
C1A C2A 1.424(11) . ?
C2A C3A 1.415(11) . ?
C2A C17A 1.445(10) . ?
C3A C5A 1.462(11) . ?
C4A H4A 0.91(7) . ?
C5A C10A 1.382(12) . ?
C5A C6A 1.406(11) . ?
C6A C7A 1.376(12) . ?
C6A H6A 0.9300 . ?
C7A C8A 1.351(12) . ?
C7A H7A 0.9300 . ?
C8A C9A 1.357(12) . ?
C9A C10A 1.402(12) . ?
C9A H9A 0.9300 . ?
C10A H10A 0.9300 . ?
C11A C12A 1.351(12) . ?
C11A C16A 1.359(12) . ?
C12A C13A 1.407(12) . ?
C12A H12A 0.9300 . ?
C13A C14A 1.341(14) . ?
C13A H13A 0.9300 . ?
C14A C15A 1.405(15) . ?
C15A C16A 1.357(13) . ?
C15A H15A 0.9300 . ?
C16A H16A 0.9300 . ?
C17A H17A 0.9300 . ?
I1B C1B 2.075(9) . ?
Cl1B C14B 1.739(9) . ?
O1B C17B 1.199(10) . ?
O2B N2B 1.212(10) . ?
O3B N2B 1.220(10) . ?
N1B C3B 1.359(9) . ?
N1B C4B 1.402(11) . ?
N1B C11B 1.437(10) . ?
N2B C8B 1.471(9) . ?
C1B C4B 1.329(12) . ?
C1B C2B 1.409(10) . ?
C4B H4B 1.11(6) . ?
C3B C2B 1.395(10) . ?
C3B C5B 1.475(10) . ?
C2B C17B 1.482(11) . ?
C5B C10B 1.377(13) . ?
C5B C6B 1.395(11) . ?
C6B C7B 1.374(11) . ?
C6B H6B 0.9300 . ?
C7B C8B 1.369(11) . ?
C7B H7B 0.9300 . ?
C8B C9B 1.387(12) . ?
C9B C10B 1.380(11) . ?
C9B H9B 0.9300 . ?
C10B H10B 0.9300 . ?
C11B C16B 1.367(12) . ?
C11B C12B 1.367(12) . ?
C12B C13B 1.404(13) . ?
C12B H12B 0.9300 . ?
C13B C14B 1.324(14) . ?
C13B H13B 0.9300 . ?
C14B C15B 1.385(15) . ?
C15B C16B 1.385(11) . ?
C15B H15B 0.9300 . ?
C16B H16B 0.9300 . ?
C17B H17B 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
C3A N1A C4A 108.4(7) . . ?
C3A N1A C11A 125.8(7) . . ?
C4A N1A C11A 124.9(7) . . ?
O3A N2A O2A 123.8(9) . . ?
O3A N2A C8A 119.1(8) . . ?
O2A N2A C8A 117.0(8) . . ?
C4A C1A C2A 109.1(8) . . ?
C4A C1A I1A 124.1(7) . . ?
C2A C1A I1A 126.8(6) . . ?
C3A C2A C1A 105.6(7) . . ?
C3A C2A C17A 124.5(8) . . ?
C1A C2A C17A 129.7(8) . . ?
N1A C3A C2A 107.5(7) . . ?
N1A C3A C5A 124.0(7) . . ?
C2A C3A C5A 128.4(7) . . ?
C1A C4A N1A 109.4(8) . . ?
C1A C4A H4A 134(5) . . ?
N1A C4A H4A 117(5) . . ?
C10A C5A C6A 118.3(8) . . ?
C10A C5A C3A 120.3(8) . . ?
C6A C5A C3A 121.3(8) . . ?
C7A C6A C5A 121.1(8) . . ?
C7A C6A H6A 119.5 . . ?
C5A C6A H6A 119.5 . . ?
C8A C7A C6A 119.1(8) . . ?
C8A C7A H7A 120.4 . . ?
C6A C7A H7A 120.4 . . ?
C7A C8A C9A 121.9(8) . . ?
C7A C8A N2A 118.1(8) . . ?
C9A C8A N2A 119.9(8) . . ?
C8A C9A C10A 120.0(9) . . ?
C8A C9A H9A 120.0 . . ?
C10A C9A H9A 120.0 . . ?
C5A C10A C9A 119.5(9) . . ?
C5A C10A H10A 120.2 . . ?
C9A C10A H10A 120.2 . . ?
C12A C11A C16A 120.7(9) . . ?
C12A C11A N1A 118.5(7) . . ?
C16A C11A N1A 120.7(8) . . ?
C11A C12A C13A 119.9(9) . . ?
C11A C12A H12A 120.0 . . ?
C13A C12A H12A 120.0 . . ?
C14A C13A C12A 119.1(9) . . ?
C14A C13A H13A 120.5 . . ?
C12A C13A H13A 120.5 . . ?
C13A C14A C15A 120.6(9) . . ?
C13A C14A Cl1A 120.2(9) . . ?
C15A C14A Cl1A 119.2(9) . . ?
C16A C15A C14A 119.1(9) . . ?
C16A C15A H15A 120.5 . . ?
C14A C15A H15A 120.5 . . ?
C15A C16A C11A 120.6(9) . . ?
C15A C16A H16A 119.7 . . ?
C11A C16A H16A 119.7 . . ?
O1A C17A C2A 125.4(9) . . ?
O1A C17A H17A 117.3 . . ?
C2A C17A H17A 117.3 . . ?
C3B N1B C4B 108.8(7) . . ?
C3B N1B C11B 127.1(7) . . ?
C4B N1B C11B 123.8(7) . . ?
O2B N2B O3B 123.4(8) . . ?
O2B N2B C8B 118.5(8) . . ?
O3B N2B C8B 118.1(9) . . ?
C4B C1B C2B 108.1(7) . . ?
C4B C1B I1B 123.3(6) . . ?
C2B C1B I1B 128.5(6) . . ?
C1B C4B N1B 108.5(7) . . ?
C1B C4B H4B 136(4) . . ?
N1B C4B H4B 115(4) . . ?
N1B C3B C2B 106.9(6) . . ?
N1B C3B C5B 124.4(7) . . ?
C2B C3B C5B 128.3(6) . . ?
C3B C2B C1B 107.6(6) . . ?
C3B C2B C17B 124.1(7) . . ?
C1B C2B C17B 128.3(8) . . ?
C10B C5B C6B 118.8(8) . . ?
C10B C5B C3B 120.9(8) . . ?
C6B C5B C3B 120.0(8) . . ?
C7B C6B C5B 120.5(8) . . ?
C7B C6B H6B 119.8 . . ?
C5B C6B H6B 119.8 . . ?
C8B C7B C6B 119.4(7) . . ?
C8B C7B H7B 120.3 . . ?
C6B C7B H7B 120.3 . . ?
C7B C8B C9B 121.5(7) . . ?
C7B C8B N2B 119.6(7) . . ?
C9B C8B N2B 118.9(8) . . ?
C10B C9B C8B 118.3(9) . . ?
C10B C9B H9B 120.9 . . ?
C8B C9B H9B 120.9 . . ?
C5B C10B C9B 121.4(9) . . ?
C5B C10B H10B 119.3 . . ?
C9B C10B H10B 119.3 . . ?
C16B C11B C12B 121.6(9) . . ?
C16B C11B N1B 118.5(7) . . ?
C12B C11B N1B 119.7(9) . . ?
C11B C12B C13B 116.9(10) . . ?
C11B C12B H12B 121.5 . . ?
C13B C12B H12B 121.5 . . ?
C14B C13B C12B 121.9(9) . . ?
C14B C13B H13B 119.0 . . ?
C12B C13B H13B 119.0 . . ?
C13B C14B C15B 121.2(9) . . ?
C13B C14B Cl1B 120.2(9) . . ?
C15B C14B Cl1B 118.5(9) . . ?
C14B C15B C16B 117.9(9) . . ?
C14B C15B H15B 121.1 . . ?
C16B C15B H15B 121.1 . . ?
C11B C16B C15B 120.4(9) . . ?
C11B C16B H16B 119.8 . . ?
C15B C16B H16B 119.8 . . ?
O1B C17B C2B 124.7(9) . . ?
O1B C17B H17B 117.7 . . ?
C2B C17B H17B 117.7 . . ?

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
C4A C1A C2A C3A 0.3(12) . . . . ?
I1A C1A C2A C3A 179.8(7) . . . . ?
C4A C1A C2A C17A -174.9(9) . . . . ?
I1A C1A C2A C17A 4.6(16) . . . . ?
C4A N1A C3A C2A -0.5(9) . . . . ?
C11A N1A C3A C2A 169.4(7) . . . . ?
C4A N1A C3A C5A 176.8(8) . . . . ?
C11A N1A C3A C5A -13.3(12) . . . . ?
C1A C2A C3A N1A 0.1(10) . . . . ?
C17A C2A C3A N1A 175.6(8) . . . . ?
C1A C2A C3A C5A -177.0(9) . . . . ?
C17A C2A C3A C5A -1.5(15) . . . . ?
C2A C1A C4A N1A -0.6(12) . . . . ?
I1A C1A C4A N1A 179.9(7) . . . . ?
C3A N1A C4A C1A 0.7(10) . . . . ?
C11A N1A C4A C1A -169.3(8) . . . . ?
N1A C3A C5A C10A -58.7(11) . . . . ?
C2A C3A C5A C10A 118.0(10) . . . . ?
N1A C3A C5A C6A 124.5(9) . . . . ?
C2A C3A C5A C6A -58.8(13) . . . . ?
C10A C5A C6A C7A -3.7(13) . . . . ?
C3A C5A C6A C7A 173.1(8) . . . . ?
C5A C6A C7A C8A 3.7(14) . . . . ?
C6A C7A C8A C9A -2.0(13) . . . . ?
C6A C7A C8A N2A -177.7(8) . . . . ?
O3A N2A C8A C7A -2.4(12) . . . . ?
O2A N2A C8A C7A 176.2(9) . . . . ?
O3A N2A C8A C9A -178.2(8) . . . . ?
O2A N2A C8A C9A 0.3(13) . . . . ?
C7A C8A C9A C10A 0.3(14) . . . . ?
N2A C8A C9A C10A 175.9(7) . . . . ?
C6A C5A C10A C9A 2.0(13) . . . . ?
C3A C5A C10A C9A -174.9(8) . . . . ?
C8A C9A C10A C5A -0.3(14) . . . . ?
C3A N1A C11A C12A -69.8(11) . . . . ?
C4A N1A C11A C12A 98.5(10) . . . . ?
C3A N1A C11A C16A 112.3(10) . . . . ?
C4A N1A C11A C16A -79.3(12) . . . . ?
C16A C11A C12A C13A 0.3(14) . . . . ?
N1A C11A C12A C13A -177.6(7) . . . . ?
C11A C12A C13A C14A -1.3(14) . . . . ?
C12A C13A C14A C15A 2.2(15) . . . . ?
C12A C13A C14A Cl1A -177.7(7) . . . . ?
C13A C14A C15A C16A -2.1(16) . . . . ?
Cl1A C14A C15A C16A 177.8(8) . . . . ?
C14A C15A C16A C11A 1.1(17) . . . . ?
C12A C11A C16A C15A -0.2(16) . . . . ?
N1A C11A C16A C15A 177.6(9) . . . . ?
C3A C2A C17A O1A -174.4(10) . . . . ?
C1A C2A C17A O1A 0.0(17) . . . . ?
C2B C1B C4B N1B 2.8(11) . . . . ?
I1B C1B C4B N1B 179.5(7) . . . . ?
C3B N1B C4B C1B -0.9(10) . . . . ?
C11B N1B C4B C1B 173.6(8) . . . . ?
C4B N1B C3B C2B -1.3(9) . . . . ?
C11B N1B C3B C2B -175.6(8) . . . . ?
C4B N1B C3B C5B -174.2(8) . . . . ?
C11B N1B C3B C5B 11.6(13) . . . . ?
N1B C3B C2B C1B 3.0(10) . . . . ?
C5B C3B C2B C1B 175.4(9) . . . . ?
N1B C3B C2B C17B -175.0(7) . . . . ?
C5B C3B C2B C17B -2.6(14) . . . . ?
C4B C1B C2B C3B -3.6(12) . . . . ?
I1B C1B C2B C3B 179.9(7) . . . . ?
C4B C1B C2B C17B 174.3(8) . . . . ?
I1B C1B C2B C17B -2.2(16) . . . . ?
N1B C3B C5B C10B 54.8(12) . . . . ?
C2B C3B C5B C10B -116.4(10) . . . . ?
N1B C3B C5B C6B -130.8(8) . . . . ?
C2B C3B C5B C6B 58.0(12) . . . . ?
C10B C5B C6B C7B 1.3(13) . . . . ?
C3B C5B C6B C7B -173.3(7) . . . . ?
C5B C6B C7B C8B 1.1(12) . . . . ?
C6B C7B C8B C9B -2.5(12) . . . . ?
C6B C7B C8B N2B 175.3(7) . . . . ?
O2B N2B C8B C7B -173.5(8) . . . . ?
O3B N2B C8B C7B 7.0(11) . . . . ?
O2B N2B C8B C9B 4.4(11) . . . . ?
O3B N2B C8B C9B -175.1(8) . . . . ?
C7B C8B C9B C10B 1.6(13) . . . . ?
N2B C8B C9B C10B -176.2(7) . . . . ?
C6B C5B C10B C9B -2.2(14) . . . . ?
C3B C5B C10B C9B 172.3(7) . . . . ?
C8B C9B C10B C5B 0.8(14) . . . . ?
C3B N1B C11B C16B 65.5(11) . . . . ?
C4B N1B C11B C16B -108.0(9) . . . . ?
C3B N1B C11B C12B -118.9(10) . . . . ?
C4B N1B C11B C12B 67.6(12) . . . . ?
C16B C11B C12B C13B -2.6(15) . . . . ?
N1B C11B C12B C13B -178.0(8) . . . . ?
C11B C12B C13B C14B 2.6(16) . . . . ?
C12B C13B C14B C15B -1.1(17) . . . . ?
C12B C13B C14B Cl1B -179.3(8) . . . . ?
C13B C14B C15B C16B -0.5(15) . . . . ?
Cl1B C14B C15B C16B 177.8(6) . . . . ?
C12B C11B C16B C15B 1.2(14) . . . . ?
N1B C11B C16B C15B 176.6(7) . . . . ?
C14B C15B C16B C11B 0.4(14) . . . . ?
C3B C2B C17B O1B 175.4(10) . . . . ?
C1B C2B C17B O1B -2.2(16) . . . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.99
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.495
_refine_diff_density_min         -0.706
_refine_diff_density_rms         0.073
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1573099'
_audit_update_record             
;
2017-09-07 deposited with the CCDC.	2020-01-16 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H10 Cl2 I N O'
_chemical_formula_sum            'C17 H10 Cl2 I N O'
_chemical_formula_weight         442.06

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'
O O 0.0106 0.0060 '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/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   6.6656(7)
_cell_length_b                   19.4376(15)
_cell_length_c                   13.2403(13)
_cell_angle_alpha                90
_cell_angle_beta                 104.291(11)
_cell_angle_gamma                90
_cell_volume                     1662.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1559
_cell_measurement_theta_min      3.9860
_cell_measurement_theta_max      27.0600

_exptl_crystal_description       block
_exptl_crystal_colour            white
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.766
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    2.247
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.66391
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 6.1049
_diffrn_reflns_number            4614
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_av_R_equivalents  0.0285
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.788
_diffrn_reflns_theta_max         25.994
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measured_fraction_theta_full 0.940
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_Laue_measured_fraction_full 0.940
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_point_group_measured_fraction_full 0.940
_reflns_number_total             3039
_reflns_number_gt                2288
_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       'CrysAlisPro (Oxford Diffraction,2010)'
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction,2010)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction,2010)'
_computing_structure_solution    'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  'PLATON (Spek,2009)'
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0367P)²+0.3021P] 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-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0058(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3039
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0383
_refine_ls_wR_factor_ref         0.0990
_refine_ls_wR_factor_gt          0.0853
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.002
_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 0.25226(5) 0.21078(2) 0.60148(3) 0.05472(18) Uani 1 1 d . . . . .
Cl2 Cl 0.6807(3) 0.41918(7) 0.31849(13) 0.0835(6) Uani 1 1 d . . . . .
Cl1 Cl 0.8258(2) 0.08721(9) 0.02063(12) 0.0691(4) Uani 1 1 d . . . . .
C5 C 0.4648(7) 0.2132(2) 0.3980(3) 0.0306(10) Uani 1 1 d . . . . .
C1 C 0.2896(6) -0.0344(2) 0.3834(4) 0.0360(10) Uani 1 1 d . . . . .
H1 H 0.348012 -0.047061 0.329189 0.043 Uiso 1 1 calc R U . . .
N1 N 0.3935(5) 0.14721(18) 0.4232(3) 0.0331(8) Uani 1 1 d . . . . .
C11 C 0.4018(6) 0.0874(2) 0.3698(3) 0.0304(10) Uani 1 1 d . . . . .
C4 C 0.2902(6) 0.1346(2) 0.5005(3) 0.0342(10) Uani 1 1 d . . . . .
C12 C 0.5068(6) 0.0849(2) 0.2845(3) 0.0311(10) Uani 1 1 d . . . . .
O1 O 0.2105(5) -0.07978(17) 0.4240(3) 0.0479(8) Uani 1 1 d . . . . .
C8 C 0.5992(8) 0.3389(2) 0.3484(4) 0.0474(13) Uani 1 1 d . . . . .
C6 C 0.6531(7) 0.2378(2) 0.4527(4) 0.0437(12) Uani 1 1 d . . . . .
H6 H 0.734993 0.212088 0.506549 0.052 Uiso 1 1 calc R U . . .
C17 C 0.7166(7) 0.1021(2) 0.3008(4) 0.0405(11) Uani 1 1 d . . . . .
H17 H 0.791878 0.113624 0.367592 0.049 Uiso 1 1 calc R U . . .
C16 C 0.8129(7) 0.1025(3) 0.2213(4) 0.0449(12) Uani 1 1 d . . . . .
H16 H 0.952103 0.114274 0.234190 0.054 Uiso 1 1 calc R U . . .
C2 C 0.3002(6) 0.0369(2) 0.4125(3) 0.0324(10) Uani 1 1 d . . . . .
C14 C 0.4993(7) 0.0664(2) 0.1034(4) 0.0431(12) Uani 1 1 d . . . . .
H14 H 0.426655 0.053730 0.036633 0.052 Uiso 1 1 calc R U . . .
C13 C 0.4028(7) 0.0664(2) 0.1846(4) 0.0385(11) Uani 1 1 d . . . . .
H13 H 0.264325 0.053620 0.171687 0.046 Uiso 1 1 calc R U . . .
C10 C 0.3459(7) 0.2508(3) 0.3179(4) 0.0460(12) Uani 1 1 d . . . . .
H10 H 0.219681 0.233402 0.280128 0.055 Uiso 1 1 calc R U . . .
C3 C 0.2315(6) 0.0678(2) 0.4954(3) 0.0379(11) Uani 1 1 d . . . . .
H3 H 0.159533 0.046134 0.538270 0.045 Uiso 1 1 calc R U . . .
C15 C 0.7052(7) 0.0855(2) 0.1225(4) 0.0415(12) Uani 1 1 d . . . . .
C7 C 0.7200(9) 0.3011(3) 0.4270(4) 0.0544(14) Uani 1 1 d . . . . .
H7 H 0.847879 0.318020 0.463491 0.065 Uiso 1 1 calc R U . . .
C9 C 0.4122(9) 0.3149(3) 0.2926(4) 0.0536(14) Uani 1 1 d . . . . .
H9 H 0.330886 0.340826 0.238775 0.064 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 C4 2.052(4) . ?
Cl2 C8 1.729(5) . ?
Cl1 C15 1.733(5) . ?
C5 C10 1.368(6) . ?
C5 C6 1.371(6) . ?
C5 N1 1.436(5) . ?
C1 O1 1.218(5) . ?
C1 C2 1.436(6) . ?
C1 H1 0.9300 . ?
N1 C11 1.370(5) . ?
N1 C4 1.389(5) . ?
C11 C2 1.389(6) . ?
C11 C12 1.469(6) . ?
C4 C3 1.352(6) . ?
C12 C13 1.380(6) . ?
C12 C17 1.402(6) . ?
C8 C7 1.364(7) . ?
C8 C9 1.365(7) . ?
C6 C7 1.378(7) . ?
C6 H6 0.9300 . ?
C17 C16 1.361(6) . ?
C17 H17 0.9300 . ?
C16 C15 1.368(6) . ?
C16 H16 0.9300 . ?
C2 C3 1.424(6) . ?
C14 C15 1.383(6) . ?
C14 C13 1.384(6) . ?
C14 H14 0.9300 . ?
C13 H13 0.9300 . ?
C10 C9 1.390(7) . ?
C10 H10 0.9300 . ?
C3 H3 0.9300 . ?
C7 H7 0.9300 . ?
C9 H9 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
C10 C5 C6 120.2(4) . . ?
C10 C5 N1 119.7(4) . . ?
C6 C5 N1 120.1(4) . . ?
O1 C1 C2 125.4(4) . . ?
O1 C1 H1 117.3 . . ?
C2 C1 H1 117.3 . . ?
C11 N1 C4 108.7(4) . . ?
C11 N1 C5 125.5(4) . . ?
C4 N1 C5 125.6(4) . . ?
N1 C11 C2 107.7(4) . . ?
N1 C11 C12 120.8(4) . . ?
C2 C11 C12 131.5(4) . . ?
C3 C4 N1 108.8(4) . . ?
C3 C4 I1 130.1(3) . . ?
N1 C4 I1 121.1(3) . . ?
C13 C12 C17 117.1(4) . . ?
C13 C12 C11 121.5(4) . . ?
C17 C12 C11 121.3(4) . . ?
C7 C8 C9 121.1(4) . . ?
C7 C8 Cl2 120.1(4) . . ?
C9 C8 Cl2 118.8(4) . . ?
C5 C6 C7 119.4(4) . . ?
C5 C6 H6 120.3 . . ?
C7 C6 H6 120.3 . . ?
C16 C17 C12 121.7(4) . . ?
C16 C17 H17 119.2 . . ?
C12 C17 H17 119.2 . . ?
C17 C16 C15 120.1(4) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C11 C2 C3 107.3(4) . . ?
C11 C2 C1 124.7(4) . . ?
C3 C2 C1 127.6(4) . . ?
C15 C14 C13 119.2(4) . . ?
C15 C14 H14 120.4 . . ?
C13 C14 H14 120.4 . . ?
C12 C13 C14 121.7(4) . . ?
C12 C13 H13 119.2 . . ?
C14 C13 H13 119.2 . . ?
C5 C10 C9 120.5(4) . . ?
C5 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C4 C3 C2 107.4(4) . . ?
C4 C3 H3 126.3 . . ?
C2 C3 H3 126.3 . . ?
C16 C15 C14 120.2(4) . . ?
C16 C15 Cl1 120.3(4) . . ?
C14 C15 Cl1 119.5(4) . . ?
C8 C7 C6 120.2(5) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C8 C9 C10 118.6(5) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 H9 120.7 . . ?

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
C10 C5 N1 C11 78.2(6) . . . . ?
C6 C5 N1 C11 -100.6(5) . . . . ?
C10 C5 N1 C4 -96.4(5) . . . . ?
C6 C5 N1 C4 84.9(5) . . . . ?
C4 N1 C11 C2 0.9(5) . . . . ?
C5 N1 C11 C2 -174.4(4) . . . . ?
C4 N1 C11 C12 -178.7(4) . . . . ?
C5 N1 C11 C12 6.0(6) . . . . ?
C11 N1 C4 C3 -0.7(5) . . . . ?
C5 N1 C4 C3 174.6(4) . . . . ?
C11 N1 C4 I1 178.1(3) . . . . ?
C5 N1 C4 I1 -6.6(6) . . . . ?
N1 C11 C12 C13 -120.7(5) . . . . ?
C2 C11 C12 C13 59.8(7) . . . . ?
N1 C11 C12 C17 58.5(6) . . . . ?
C2 C11 C12 C17 -121.0(5) . . . . ?
C10 C5 C6 C7 0.8(7) . . . . ?
N1 C5 C6 C7 179.6(5) . . . . ?
C13 C12 C17 C16 1.7(7) . . . . ?
C11 C12 C17 C16 -177.5(4) . . . . ?
C12 C17 C16 C15 -0.2(8) . . . . ?
N1 C11 C2 C3 -0.8(5) . . . . ?
C12 C11 C2 C3 178.7(4) . . . . ?
N1 C11 C2 C1 -174.8(4) . . . . ?
C12 C11 C2 C1 4.8(7) . . . . ?
O1 C1 C2 C11 175.9(4) . . . . ?
O1 C1 C2 C3 3.3(7) . . . . ?
C17 C12 C13 C14 -1.6(7) . . . . ?
C11 C12 C13 C14 177.7(4) . . . . ?
C15 C14 C13 C12 -0.1(7) . . . . ?
C6 C5 C10 C9 -1.4(8) . . . . ?
N1 C5 C10 C9 179.8(4) . . . . ?
N1 C4 C3 C2 0.2(5) . . . . ?
I1 C4 C3 C2 -178.5(3) . . . . ?
C11 C2 C3 C4 0.4(5) . . . . ?
C1 C2 C3 C4 174.1(4) . . . . ?
C17 C16 C15 C14 -1.5(8) . . . . ?
C17 C16 C15 Cl1 179.0(4) . . . . ?
C13 C14 C15 C16 1.6(7) . . . . ?
C13 C14 C15 Cl1 -178.8(4) . . . . ?
C9 C8 C7 C6 -1.0(9) . . . . ?
Cl2 C8 C7 C6 178.4(4) . . . . ?
C5 C6 C7 C8 0.4(8) . . . . ?
C7 C8 C9 C10 0.4(8) . . . . ?
Cl2 C8 C9 C10 -179.0(4) . . . . ?
C5 C10 C9 C8 0.8(8) . . . . ?

_refine_diff_density_max         0.560
_refine_diff_density_min         -0.613
_refine_diff_density_rms         0.087

