# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1023121'
_audit_update_record             
;
2018-05-11 deposited with the CCDC.
2018-05-24 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         ?
_chemical_formula_sum            'C15 H12 I2 N2'
_chemical_formula_weight         474.07

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'
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           1
_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'

_cell_length_a                   8.3611(2)
_cell_length_b                   10.3462(2)
_cell_length_c                   10.3808(3)
_cell_angle_alpha                106.747(3)
_cell_angle_beta                 113.735(3)
_cell_angle_gamma                103.091(3)
_cell_volume                     724.61(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    11792
_cell_measurement_theta_min      2.8830
_cell_measurement_theta_max      28.6285

_cell_measurement_temperature    150(2)
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.07
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.173
_exptl_crystal_F_000             444
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    4.328
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.7015
_exptl_absorpt_correction_T_max  1.2349
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.19 (release 28-02-2008 CrysAlis171 .NET)
(compiled Feb 28 2008,12:10:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 16.3990
_diffrn_measurement_device_type  'Xcalibur Oxford diffraction'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            12928
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_av_R_equivalents  0.0192
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.664
_diffrn_reflns_theta_max         26.437
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.900
_diffrn_reflns_point_group_measured_fraction_full 0.917
_reflns_number_total             5374
_reflns_number_gt                5216
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.807
_reflns_Friedel_fraction_max     0.804
_reflns_Friedel_fraction_full    0.837

_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       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.32.19 (release 28-02-2008 CrysAlis171 .NET)
(compiled Feb 28 2008,12:10:31)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.19 (release 28-02-2008 CrysAlis171 .NET)
(compiled Feb 28 2008,12:10:31)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.32.19 (release 28-02-2008 CrysAlis171 .NET)
(compiled Feb 28 2008,12:10:31)
;
_computing_structure_solution    'SHELXTL Brüker'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0251P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2300 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.005(9)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         5374
_refine_ls_number_parameters     407
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0181
_refine_ls_R_factor_gt           0.0171
_refine_ls_wR_factor_ref         0.0403
_refine_ls_wR_factor_gt          0.0400
_refine_ls_goodness_of_fit_ref   1.059
_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 -0.36170(4) 0.47567(3) -0.02981(3) 0.02483(9) Uani 1 1 d . . . . .
N1 N 0.2681(6) 0.1465(5) 0.0279(5) 0.0228(9) Uani 1 1 d . . . . .
C1 C -0.2516(7) 0.3136(5) -0.0635(5) 0.0186(10) Uani 1 1 d . . . . .
I2 I 0.15847(4) -0.15401(3) 0.45080(4) 0.02910(9) Uani 1 1 d . . . . .
C2 C -0.3774(7) 0.1697(5) -0.1611(6) 0.0214(11) Uani 1 1 d . . . . .
H2 H -0.507476 0.145257 -0.204470 0.026 Uiso 1 1 calc R U . . .
N2 N -0.0518(6) -0.0131(5) -0.1787(5) 0.0239(9) Uani 1 1 d . . . . .
C3 C -0.3090(8) 0.0639(6) -0.1931(6) 0.0216(11) Uani 1 1 d . . . . .
H3 H -0.393710 -0.032862 -0.258675 0.026 Uiso 1 1 calc R U . . .
C4 C -0.1142(7) 0.0980(5) -0.1292(5) 0.0170(10) Uani 1 1 d . . . . .
C5 C 0.0121(7) 0.2402(6) -0.0250(6) 0.0187(11) Uani 1 1 d . . . . .
C6 C -0.0578(7) 0.3498(5) 0.0074(5) 0.0188(10) Uani 1 1 d . . . . .
H6 H 0.025838 0.446204 0.076207 0.023 Uiso 1 1 calc R U . . .
C7 C 0.2250(7) 0.2791(5) 0.0554(6) 0.0226(10) Uani 1 1 d . . . . .
H7A H 0.275(9) 0.332(7) 0.016(7) 0.034(16) Uiso 1 1 d . . . . .
H7B H 0.284(7) 0.332(5) 0.172(6) 0.013(12) Uiso 1 1 d . . . . .
C8 C 0.2405(7) 0.0758(5) 0.1206(6) 0.0192(10) Uani 1 1 d . . . . .
C9 C 0.3754(7) 0.1370(5) 0.2779(6) 0.0198(10) Uani 1 1 d . . . . .
H9 H 0.471(8) 0.229(7) 0.303(6) 0.026(15) Uiso 1 1 d . . . . .
C10 C 0.3551(7) 0.0729(5) 0.3732(5) 0.0204(10) Uani 1 1 d . . . . .
H10 H 0.445539 0.115100 0.478365 0.024 Uiso 1 1 calc R U . . .
C11 C 0.1999(7) -0.0541(5) 0.3109(6) 0.0202(10) Uani 1 1 d . . . . .
C12 C 0.0649(7) -0.1172(5) 0.1555(6) 0.0215(11) Uani 1 1 d . . . . .
H12 H -0.039642 -0.203004 0.114621 0.026 Uiso 1 1 calc R U . . .
C13 C 0.0852(7) -0.0528(5) 0.0603(6) 0.0201(10) Uani 1 1 d . . . . .
C14 C -0.0694(8) -0.1176(6) -0.1096(6) 0.0236(13) Uani 1 1 d . . . . .
H14A H -0.202(8) -0.154(6) -0.127(6) 0.015(13) Uiso 1 1 d . . . . .
H14B H -0.079(8) -0.207(7) -0.178(7) 0.031(16) Uiso 1 1 d . . . . .
C15 C 0.1449(8) 0.0481(6) -0.1374(6) 0.0270(12) Uani 1 1 d . . . . .
H15A H 0.194(7) -0.027(5) -0.153(6) 0.015(12) Uiso 1 1 d . . . . .
H15B H 0.135(8) 0.103(6) -0.208(6) 0.022(13) Uiso 1 1 d . . . . .
I3 I 0.29239(5) -0.32467(4) -0.07126(4) 0.03739(12) Uani 1 1 d . . . . .
N3 N 0.9795(6) 0.1783(4) 0.5620(5) 0.0210(9) Uani 1 1 d . . . . .
I4 I 0.47529(5) 0.60165(4) 0.53484(4) 0.03160(10) Uani 1 1 d . . . . .
N4 N 1.0285(6) 0.3240(4) 0.4262(5) 0.0232(9) Uani 1 1 d . . . . .
C30 C 0.5259(7) -0.1600(5) 0.1394(6) 0.0239(11) Uani 1 1 d . . . . .
C31 C 0.6434(8) -0.0445(5) 0.1370(6) 0.0246(11) Uani 1 1 d . . . . .
H31 H 0.621586 -0.042738 0.042426 0.029 Uiso 1 1 calc R U . . .
C32 C 0.7938(7) 0.0692(5) 0.2747(6) 0.0209(10) Uani 1 1 d . . . . .
C33 C 0.8259(7) 0.0628(6) 0.4167(6) 0.0170(12) Uani 1 1 d . . . . .
C34 C 0.7107(7) -0.0540(5) 0.4176(6) 0.0217(11) Uani 1 1 d . . . . .
H34 H 0.734471 -0.058161 0.511566 0.026 Uiso 1 1 calc R U . . .
C35 C 0.5582(7) -0.1666(5) 0.2790(6) 0.0247(11) Uani 1 1 d . . . . .
H35 H 0.479078 -0.245253 0.279902 0.030 Uiso 1 1 calc R U . . .
C36 C 0.9193(8) 0.1976(6) 0.2722(6) 0.0238(10) Uani 1 1 d . . . . .
H36A H 1.013(7) 0.170(5) 0.240(5) 0.008(11) Uiso 1 1 d . . . . .
H36B H 0.841(7) 0.236(5) 0.191(6) 0.012(12) Uiso 1 1 d . . . . .
C37 C 0.9159(6) 0.3942(5) 0.4637(5) 0.0191(10) Uani 1 1 d . . . . .
C38 C 0.8524(8) 0.4785(6) 0.3871(6) 0.0259(11) Uani 1 1 d . . . . .
H38 H 0.889(9) 0.495(7) 0.321(8) 0.039(18) Uiso 1 1 d . . . . .
C39 C 0.7352(8) 0.5434(5) 0.4128(6) 0.0257(11) Uani 1 1 d . . . . .
H39 H 0.700(9) 0.600(8) 0.367(8) 0.049(19) Uiso 1 1 d . . . . .
C40 C 0.6809(7) 0.5254(5) 0.5172(6) 0.0218(10) Uani 1 1 d . . . . .
C41 C 0.7443(7) 0.4465(5) 0.5985(6) 0.0200(10) Uani 1 1 d . . . . .
H41 H 0.693(8) 0.436(6) 0.672(7) 0.033(15) Uiso 1 1 d . . . . .
C42 C 0.8628(8) 0.3773(6) 0.5695(6) 0.0196(12) Uani 1 1 d . . . . .
C43 C 0.9151(8) 0.2752(5) 0.6437(5) 0.0204(10) Uani 1 1 d . . . . .
H43A H 1.025(9) 0.325(7) 0.752(8) 0.036(17) Uiso 1 1 d . . . . .
H43B H 0.818(8) 0.214(6) 0.649(6) 0.017(13) Uiso 1 1 d . . . . .
C44 C 1.1195(8) 0.2703(6) 0.5396(6) 0.0258(11) Uani 1 1 d . . . . .
H44A H 1.231(8) 0.360(6) 0.640(7) 0.023(14) Uiso 1 1 d . . . . .
H44B H 1.194(8) 0.227(6) 0.515(7) 0.024(15) 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
I1 C1 2.098(5) . ?
N1 C8 1.423(6) . ?
N1 C15 1.462(7) . ?
N1 C7 1.474(6) . ?
C1 C6 1.383(7) . ?
C1 C2 1.383(7) . ?
I2 C11 2.099(5) . ?
C2 C3 1.365(7) . ?
C2 H2 0.9300 . ?
N2 C4 1.416(6) . ?
N2 C15 1.447(7) . ?
N2 C14 1.471(7) . ?
C3 C4 1.397(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(7) . ?
C5 C6 1.408(7) . ?
C5 C7 1.521(7) . ?
C6 H6 0.9300 . ?
C7 H7A 0.89(7) . ?
C7 H7B 1.01(5) . ?
C8 C13 1.389(7) . ?
C8 C9 1.392(7) . ?
C9 C10 1.382(7) . ?
C9 H9 0.98(6) . ?
C10 C11 1.375(7) . ?
C10 H10 0.9300 . ?
C11 C12 1.377(7) . ?
C12 C13 1.383(7) . ?
C12 H12 0.9300 . ?
C13 C14 1.524(7) . ?
C14 H14A 1.00(5) . ?
C14 H14B 0.95(6) . ?
C15 H15A 0.96(5) . ?
C15 H15B 1.04(6) . ?
I3 C30 2.099(5) . ?
N3 C33 1.435(6) . ?
N3 C43 1.462(6) . ?
N3 C44 1.473(7) . ?
I4 C40 2.096(5) . ?
N4 C37 1.417(7) . ?
N4 C44 1.457(7) . ?
N4 C36 1.476(7) . ?
C30 C31 1.378(8) . ?
C30 C35 1.389(8) . ?
C31 C32 1.386(7) . ?
C31 H31 0.9300 . ?
C32 C33 1.413(7) . ?
C32 C36 1.509(7) . ?
C33 C34 1.370(8) . ?
C34 C35 1.392(7) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
C36 H36A 1.03(5) . ?
C36 H36B 1.07(5) . ?
C37 C42 1.379(8) . ?
C37 C38 1.394(7) . ?
C38 C39 1.374(8) . ?
C38 H38 0.90(7) . ?
C39 C40 1.374(8) . ?
C39 H39 0.88(7) . ?
C40 C41 1.376(7) . ?
C41 C42 1.423(8) . ?
C41 H41 1.03(6) . ?
C42 C43 1.518(7) . ?
C43 H43A 1.00(6) . ?
C43 H43B 0.95(6) . ?
C44 H44A 1.04(6) . ?
C44 H44B 0.92(6) . ?

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
C8 N1 C15 110.6(4) . . ?
C8 N1 C7 112.1(4) . . ?
C15 N1 C7 107.4(4) . . ?
C6 C1 C2 120.6(4) . . ?
C6 C1 I1 120.9(3) . . ?
C2 C1 I1 118.4(4) . . ?
C3 C2 C1 119.4(5) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C4 N2 C15 111.5(4) . . ?
C4 N2 C14 112.1(4) . . ?
C15 N2 C14 107.5(4) . . ?
C2 C3 C4 121.3(5) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 119.4(4) . . ?
C5 C4 N2 121.6(5) . . ?
C3 C4 N2 118.9(4) . . ?
C4 C5 C6 119.3(5) . . ?
C4 C5 C7 120.8(4) . . ?
C6 C5 C7 119.8(5) . . ?
C1 C6 C5 119.7(4) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
N1 C7 C5 111.4(4) . . ?
N1 C7 H7A 108(4) . . ?
C5 C7 H7A 109(4) . . ?
N1 C7 H7B 106(3) . . ?
C5 C7 H7B 110(3) . . ?
H7A C7 H7B 113(5) . . ?
C13 C8 C9 118.6(5) . . ?
C13 C8 N1 122.7(4) . . ?
C9 C8 N1 118.7(4) . . ?
C10 C9 C8 121.0(4) . . ?
C10 C9 H9 130(3) . . ?
C8 C9 H9 108(3) . . ?
C11 C10 C9 119.3(4) . . ?
C11 C10 H10 120.4 . . ?
C9 C10 H10 120.4 . . ?
C10 C11 C12 120.8(4) . . ?
C10 C11 I2 121.0(4) . . ?
C12 C11 I2 118.2(3) . . ?
C11 C12 C13 119.8(4) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C8 120.4(4) . . ?
C12 C13 C14 119.9(4) . . ?
C8 C13 C14 119.5(5) . . ?
N2 C14 C13 111.7(4) . . ?
N2 C14 H14A 109(3) . . ?
C13 C14 H14A 114(3) . . ?
N2 C14 H14B 107(4) . . ?
C13 C14 H14B 117(4) . . ?
H14A C14 H14B 97(4) . . ?
N2 C15 N1 112.1(4) . . ?
N2 C15 H15A 111(3) . . ?
N1 C15 H15A 104(3) . . ?
N2 C15 H15B 100(3) . . ?
N1 C15 H15B 113(3) . . ?
H15A C15 H15B 116(4) . . ?
C33 N3 C43 112.4(4) . . ?
C33 N3 C44 111.4(4) . . ?
C43 N3 C44 107.2(4) . . ?
C37 N4 C44 111.6(4) . . ?
C37 N4 C36 113.2(4) . . ?
C44 N4 C36 107.0(4) . . ?
C31 C30 C35 120.8(5) . . ?
C31 C30 I3 119.1(4) . . ?
C35 C30 I3 120.1(4) . . ?
C30 C31 C32 120.4(5) . . ?
C30 C31 H31 119.8 . . ?
C32 C31 H31 119.8 . . ?
C31 C32 C33 118.7(5) . . ?
C31 C32 C36 120.4(5) . . ?
C33 C32 C36 120.9(4) . . ?
C34 C33 C32 120.4(5) . . ?
C34 C33 N3 119.0(5) . . ?
C32 C33 N3 120.6(5) . . ?
C33 C34 C35 120.6(5) . . ?
C33 C34 H34 119.7 . . ?
C35 C34 H34 119.7 . . ?
C30 C35 C34 119.1(5) . . ?
C30 C35 H35 120.4 . . ?
C34 C35 H35 120.4 . . ?
N4 C36 C32 111.1(4) . . ?
N4 C36 H36A 109(3) . . ?
C32 C36 H36A 111(3) . . ?
N4 C36 H36B 106(3) . . ?
C32 C36 H36B 113(3) . . ?
H36A C36 H36B 106(4) . . ?
C42 C37 C38 119.5(5) . . ?
C42 C37 N4 121.8(5) . . ?
C38 C37 N4 118.6(4) . . ?
C39 C38 C37 121.4(5) . . ?
C39 C38 H38 117(4) . . ?
C37 C38 H38 122(4) . . ?
C40 C39 C38 119.1(5) . . ?
C40 C39 H39 120(5) . . ?
C38 C39 H39 121(5) . . ?
C39 C40 C41 121.5(5) . . ?
C39 C40 I4 118.8(4) . . ?
C41 C40 I4 119.4(4) . . ?
C40 C41 C42 119.2(5) . . ?
C40 C41 H41 116(3) . . ?
C42 C41 H41 125(3) . . ?
C37 C42 C41 119.2(5) . . ?
C37 C42 C43 120.6(5) . . ?
C41 C42 C43 120.0(5) . . ?
N3 C43 C42 111.6(4) . . ?
N3 C43 H43A 102(3) . . ?
C42 C43 H43A 115(4) . . ?
N3 C43 H43B 106(3) . . ?
C42 C43 H43B 116(3) . . ?
H43A C43 H43B 105(5) . . ?
N4 C44 N3 111.1(4) . . ?
N4 C44 H44A 108(3) . . ?
N3 C44 H44A 115(3) . . ?
N4 C44 H44B 110(4) . . ?
N3 C44 H44B 115(4) . . ?
H44A C44 H44B 96(4) . . ?

_refine_diff_density_max         0.374
_refine_diff_density_min         -0.976
_refine_diff_density_rms         0.103

####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1822048'
_audit_update_record             
;
2018-05-23 deposited with the CCDC.
2018-05-24 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         ?
_chemical_formula_sum            'C19.40 H12.80 Cl0.80 I2 N2'
_chemical_formula_weight         556.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      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                   11.6765(2)
_cell_length_b                   22.8696(4)
_cell_length_c                   8.36360(10)
_cell_angle_alpha                90
_cell_angle_beta                 110.549(2)
_cell_angle_gamma                90
_cell_volume                     2091.28(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.00(10)
_cell_measurement_reflns_used    7696
_cell_measurement_theta_min      3.8625
_cell_measurement_theta_max      73.8707
_cell_oxdiff_length_a            11.6744(3)
_cell_oxdiff_length_b            22.8677(6)
_cell_oxdiff_length_c            8.36492(19)
_cell_oxdiff_angle_alpha         90.015(2)
_cell_oxdiff_angle_beta          110.532(2)
_cell_oxdiff_angle_gamma         89.990(2)
_cell_oxdiff_volume              2091.28(9)
_cell_oxdiff_measurement_reflns_used 7694

_exptl_crystal_description       Neddle
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.3779
_exptl_crystal_size_mid          0.0550
_exptl_crystal_size_min          0.0509
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.766
_exptl_crystal_F_000             1051
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    24.576
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.071
_exptl_absorpt_correction_T_max  0.402
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_diffrn_ambient_temperature      100.00(10)
_diffrn_radiation_wavelength     1.5418
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Single source at offset), Atlas'
_diffrn_detector_area_resol_mean 5.2012
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_number            15502
_diffrn_reflns_av_unetI/netI     0.0337
_diffrn_reflns_av_R_equivalents  0.0382
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.866
_diffrn_reflns_theta_max         74.036
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4184
_reflns_number_gt                3835
_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, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET)
(compiled Jan 23 2012,18:06:46)
;
_computing_structure_solution    'SHELXTL Bruker'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0702P)²+13.1573P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4184
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0419
_refine_ls_R_factor_gt           0.0386
_refine_ls_wR_factor_ref         0.1151
_refine_ls_wR_factor_gt          0.1120
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_restrained_S_all      0.976
_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 -0.03537(3) 0.76023(2) 0.13153(4) 0.01855(12) Uani 1 1 d . . . . .
N1 N 0.1478(4) 0.36893(19) 0.3772(5) 0.0160(8) Uani 1 1 d . . . . .
C1 C 0.0311(5) 0.6779(2) 0.1520(7) 0.0208(11) Uani 1 1 d . . . . .
I2 I 0.72469(3) 0.43988(2) 1.37911(4) 0.02816(13) Uani 1 1 d . . . . .
N2 N 0.2800(4) 0.40353(19) 0.2293(5) 0.0161(8) Uani 1 1 d . . . . .
C2 C 0.0648(5) 0.6283(2) 0.1598(7) 0.0197(11) Uani 1 1 d . . . . .
C3 C 0.1123(5) 0.5700(2) 0.1685(6) 0.0170(10) Uani 1 1 d . . . . .
C4 C 0.2156(5) 0.5600(2) 0.1226(7) 0.0171(10) Uani 1 1 d . . . . .
H4 H 0.248883 0.590391 0.079355 0.020 Uiso 1 1 calc R U . . .
C5 C 0.2676(5) 0.5051(2) 0.1419(6) 0.0183(10) Uani 1 1 d . . . . .
H5 H 0.335982 0.498854 0.111530 0.022 Uiso 1 1 calc R U . . .
C6 C 0.2191(4) 0.4589(2) 0.2060(6) 0.0147(9) Uani 1 1 d . . . . .
C7 C 0.1129(5) 0.4675(2) 0.2463(6) 0.0161(10) Uani 1 1 d . . . . .
C8 C 0.0611(5) 0.5229(2) 0.2263(6) 0.0165(10) Uani 1 1 d . . . . .
H8 H -0.009314 0.528772 0.251924 0.020 Uiso 1 1 calc R U . . .
C9 C 0.0595(4) 0.4173(2) 0.3151(7) 0.0169(10) Uani 1 1 d . . . . .
H9B H 0.035307 0.431307 0.408068 0.020 Uiso 1 1 calc R U . . .
H9A H -0.013067 0.402903 0.225771 0.020 Uiso 1 1 calc R U . . .
C10 C 0.2428(4) 0.3821(2) 0.5364(6) 0.0144(9) Uani 1 1 d . . . . .
C11 C 0.2153(5) 0.3793(2) 0.6864(7) 0.0190(10) Uani 1 1 d . . . . .
H11 H 0.136517 0.369668 0.680497 0.023 Uiso 1 1 calc R U . . .
C12 C 0.3042(5) 0.3907(2) 0.8427(7) 0.0218(11) Uani 1 1 d . . . . .
H12 H 0.285006 0.389015 0.941513 0.026 Uiso 1 1 calc R U . . .
C13 C 0.4243(5) 0.4048(2) 0.8532(7) 0.0198(10) Uani 1 1 d . . . . .
C14 C 0.4504(5) 0.4074(2) 0.7034(7) 0.0205(11) Uani 1 1 d . . . . .
H14 H 0.529516 0.416315 0.709610 0.025 Uiso 1 1 calc R U . . .
C15 C 0.3611(5) 0.3969(2) 0.5445(6) 0.0147(9) Uani 1 1 d . . . . .
C16 C 0.5178(5) 0.4162(3) 1.0163(7) 0.0238(11) Uani 1 1 d . . . . .
C17 C 0.5980(5) 0.4247(3) 1.1519(6) 0.0186(10) Uani 1 1 d . . . . .
C18 C 0.3923(5) 0.4028(2) 0.3827(6) 0.0164(10) Uani 1 1 d . . . . .
H18B H 0.437740 0.438657 0.387798 0.020 Uiso 1 1 calc R U . . .
H18A H 0.443586 0.370291 0.375385 0.020 Uiso 1 1 calc R U . . .
C19 C 0.2003(5) 0.3564(2) 0.2440(6) 0.0170(10) Uani 1 1 d . . . . .
H19B H 0.246696 0.320243 0.271655 0.020 Uiso 1 1 calc R U . . .
H19A H 0.134648 0.351054 0.135205 0.020 Uiso 1 1 calc R U . . .
Cl1 Cl 0.4283(10) 0.2583(5) 0.1102(14) 0.106(3) Uiso 0.4 1 d . . P . .
Cl2 Cl 0.648(2) 0.2161(10) 0.138(3) 0.134(6) Uiso 0.25 1 d . . P . .
C50 C 0.597(7) 0.250(3) 0.223(10) 0.11(2) Uiso 0.25 1 d . . P . .
C51 C 0.576(8) 0.257(4) 0.094(12) 0.08(2) Uiso 0.15 1 d . . P . .
Cl3 Cl 0.564(4) 0.248(2) -0.127(6) 0.164(15) Uiso 0.15 1 d . . P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.021(5) . ?
N1 C10 1.435(6) . ?
N1 C19 1.476(6) . ?
N1 C9 1.476(6) . ?
C1 C2 1.194(8) . ?
I2 C17 1.987(5) . ?
N2 C6 1.432(7) . ?
N2 C19 1.458(7) . ?
N2 C18 1.478(6) . ?
C2 C3 1.438(7) . ?
C3 C8 1.397(8) . ?
C3 C4 1.407(7) . ?
C4 C5 1.378(8) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(7) . ?
C5 H5 0.9300 . ?
C6 C7 1.408(7) . ?
C7 C8 1.389(7) . ?
C7 C9 1.512(7) . ?
C8 H8 0.9300 . ?
C9 H9B 0.9700 . ?
C9 H9A 0.9700 . ?
C10 C15 1.401(7) . ?
C10 C11 1.401(7) . ?
C11 C12 1.379(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.411(8) . ?
C12 H12 0.9300 . ?
C13 C14 1.390(8) . ?
C13 C16 1.441(8) . ?
C14 C15 1.392(7) . ?
C14 H14 0.9300 . ?
C15 C18 1.525(7) . ?
C16 C17 1.206(8) . ?
C18 H18B 0.9700 . ?
C18 H18A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 H19A 0.9700 . ?
Cl1 C51 1.78(9) . ?
Cl1 C50 1.87(8) . ?
Cl1 Cl3 2.22(5) 4_566 ?
Cl2 C51 1.23(9) . ?
Cl2 C50 1.33(8) . ?
Cl2 Cl3 2.21(5) . ?
C50 C51 1.03(10) . ?
C50 Cl3 1.44(8) 4_566 ?
C51 Cl3 1.81(9) . ?

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 N1 C19 110.5(4) . . ?
C10 N1 C9 112.7(4) . . ?
C19 N1 C9 107.7(4) . . ?
C2 C1 I1 176.8(5) . . ?
C6 N2 C19 111.4(4) . . ?
C6 N2 C18 112.0(4) . . ?
C19 N2 C18 108.4(4) . . ?
C1 C2 C3 176.5(6) . . ?
C8 C3 C4 118.7(5) . . ?
C8 C3 C2 122.0(5) . . ?
C4 C3 C2 119.3(5) . . ?
C5 C4 C3 120.0(5) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.9(5) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C7 119.9(5) . . ?
C5 C6 N2 118.3(4) . . ?
C7 C6 N2 121.8(5) . . ?
C8 C7 C6 118.7(5) . . ?
C8 C7 C9 121.2(5) . . ?
C6 C7 C9 120.1(5) . . ?
C7 C8 C3 121.6(5) . . ?
C7 C8 H8 119.2 . . ?
C3 C8 H8 119.2 . . ?
N1 C9 C7 111.8(4) . . ?
N1 C9 H9B 109.3 . . ?
C7 C9 H9B 109.3 . . ?
N1 C9 H9A 109.3 . . ?
C7 C9 H9A 109.3 . . ?
H9B C9 H9A 107.9 . . ?
C15 C10 C11 120.0(5) . . ?
C15 C10 N1 121.6(4) . . ?
C11 C10 N1 118.4(4) . . ?
C12 C11 C10 120.5(5) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 120.2(5) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C14 C13 C12 118.7(5) . . ?
C14 C13 C16 120.8(5) . . ?
C12 C13 C16 120.4(5) . . ?
C13 C14 C15 121.7(5) . . ?
C13 C14 H14 119.1 . . ?
C15 C14 H14 119.1 . . ?
C14 C15 C10 118.8(5) . . ?
C14 C15 C18 120.0(5) . . ?
C10 C15 C18 121.1(4) . . ?
C17 C16 C13 178.3(7) . . ?
C16 C17 I2 177.6(5) . . ?
N2 C18 C15 110.9(4) . . ?
N2 C18 H18B 109.5 . . ?
C15 C18 H18B 109.5 . . ?
N2 C18 H18A 109.5 . . ?
C15 C18 H18A 109.5 . . ?
H18B C18 H18A 108.1 . . ?
N2 C19 N1 111.5(4) . . ?
N2 C19 H19B 109.3 . . ?
N1 C19 H19B 109.3 . . ?
N2 C19 H19A 109.3 . . ?
N1 C19 H19A 109.3 . . ?
H19B C19 H19A 108.0 . . ?
C51 Cl1 C50 33(3) . . ?
C51 Cl1 Cl3 73(3) . 4_566 ?
C50 Cl1 Cl3 40(3) . 4_566 ?
C51 Cl2 C50 47(5) . . ?
C51 Cl2 Cl3 55(4) . . ?
C50 Cl2 Cl3 102(4) . . ?
C51 C50 Cl2 61(6) . . ?
C51 C50 Cl3 151(9) . 4_566 ?
Cl2 C50 Cl3 142(6) . 4_566 ?
C51 C50 Cl1 69(7) . . ?
Cl2 C50 Cl1 112(5) . . ?
Cl3 C50 Cl1 83(4) 4_566 . ?
C50 C51 Cl2 71(7) . . ?
C50 C51 Cl1 79(7) . . ?
Cl2 C51 Cl1 125(6) . . ?
C50 C51 Cl3 162(9) . . ?
Cl2 C51 Cl3 91(5) . . ?
Cl1 C51 Cl3 110(5) . . ?
C50 Cl3 C51 159(5) 4_565 . ?
C50 Cl3 Cl2 136(4) 4_565 . ?
C51 Cl3 Cl2 34(3) . . ?
C50 Cl3 Cl1 57(3) 4_565 4_565 ?
C51 Cl3 Cl1 142(4) . 4_565 ?
Cl2 Cl3 Cl1 152(2) . 4_565 ?

_refine_diff_density_max         1.809
_refine_diff_density_min         -1.249
_refine_diff_density_rms         0.183

####################################################################### 
# 
# 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_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1023123'
_audit_update_record             
;
2018-05-11 deposited with the CCDC.
2018-05-24 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         ?
_chemical_formula_sum            'C16 H14 Cl2 I2 N2'
_chemical_formula_weight         558.99

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      orthorhombic
_space_group_IT_number           45
_space_group_name_H-M_alt        'I b a 2'
_space_group_name_Hall           'I 2 -2c'

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

_cell_length_a                   17.8602(6)
_cell_length_b                   17.9174(6)
_cell_length_c                   11.0199(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3526.5(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       Plate
_exptl_crystal_colour            Yellow
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.106
_exptl_crystal_F_000             2112
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    3.867
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_T_min  0.548
_exptl_absorpt_correction_T_max  0.922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.10 (release 13-04-2006 CrysAlis171 .NET)
(compiled Apr 13 2006,12:24:59)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Oxford Diffraction'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.3990
_diffrn_reflns_number            8976
_diffrn_reflns_av_unetI/netI     0.0629
_diffrn_reflns_av_R_equivalents  0.1321
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.145
_diffrn_reflns_theta_max         24.752
_diffrn_reflns_theta_full        24.752
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.862
_diffrn_reflns_point_group_measured_fraction_full 0.862
_reflns_number_total             2614
_reflns_number_gt                2553
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.660
_reflns_Friedel_fraction_max     0.730
_reflns_Friedel_fraction_full    0.730

_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       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.29.10 (release 13-04-2006 CrysAlis171 .NET)
(compiled Apr 13 2006,12:24:59)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.10 (release 13-04-2006 CrysAlis171 .NET)
(compiled Apr 13 2006,12:24:59)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.10 (release 13-04-2006 CrysAlis171 .NET)
(compiled Apr 13 2006,12:24:59)
;
_computing_structure_solution    'SHELXTL Brüker'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0683P)²+4.2667P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.02(8)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         2614
_refine_ls_number_parameters     194
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0652
_refine_ls_R_factor_gt           0.0646
_refine_ls_wR_factor_ref         0.1611
_refine_ls_wR_factor_gt          0.1603
_refine_ls_goodness_of_fit_ref   1.763
_refine_ls_restrained_S_all      1.763
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1 I 0.21568(4) 0.45583(5) 0.19520(9) 0.0222(3) Uani 1 1 d . . . . .
C1 C 0.3123(8) 0.4503(9) 0.3050(13) 0.023(3) Uani 1 1 d . . . . .
N1 N 0.4933(6) 0.4331(9) 0.5480(13) 0.025(3) Uani 1 1 d . . . . .
I2 I 0.48725(5) 0.72786(5) 0.17853(11) 0.0285(4) Uani 1 1 d . . . . .
C2 C 0.3388(8) 0.5146(9) 0.3615(13) 0.022(3) Uani 1 1 d . . . . .
H2 H 0.314936 0.560148 0.349195 0.027 Uiso 1 1 calc R U . . .
N2 N 0.5646(6) 0.9801(7) 0.5567(11) 0.019(2) Uani 1 1 d . . . . .
C3 C 0.4008(6) 0.5100(10) 0.4360(15) 0.022(3) Uani 1 1 d . . . . .
C4 C 0.4327(7) 0.4413(9) 0.4605(13) 0.017(3) Uani 1 1 d . . . . .
C5 C 0.4074(8) 0.3781(9) 0.4033(14) 0.022(3) Uani 1 1 d . . . . .
H5 H 0.430743 0.332499 0.417499 0.026 Uiso 1 1 calc R U . . .
C6 C 0.3463(8) 0.3821(9) 0.3232(13) 0.025(3) Uani 1 1 d . . . . .
H6 H 0.329208 0.339700 0.283266 0.030 Uiso 1 1 calc R U . . .
C7 C 0.5659(8) 0.4196(9) 0.4900(14) 0.022(3) Uani 1 1 d . . . . .
H7A H 0.559697 0.382694 0.426372 0.026 Uiso 1 1 calc R U . . .
H7B H 0.600291 0.399352 0.549589 0.026 Uiso 1 1 calc R U . . .
C8 C 0.500000 0.500000 0.623(2) 0.020(4) Uiso 1 2 d S . P . .
H8A H 0.456270 0.504280 0.674686 0.024 Uiso 1 1 d R U . . .
C10 C 0.5129(8) 0.8131(10) 0.3002(14) 0.025(3) Uani 1 1 d . . . . .
C11 C 0.5867(8) 0.8338(10) 0.3214(14) 0.025(3) Uani 1 1 d . . . . .
H11 H 0.625385 0.810601 0.279445 0.029 Uiso 1 1 calc R U . . .
C12 C 0.6024(7) 0.8895(8) 0.4056(15) 0.023(3) Uani 1 1 d . . . . .
H12 H 0.651952 0.902686 0.420047 0.028 Uiso 1 1 calc R U . . .
C13 C 0.5469(8) 0.9252(9) 0.4675(14) 0.018(3) Uani 1 1 d . . . . .
C14 C 0.4714(8) 0.9060(8) 0.4419(13) 0.019(3) Uani 1 1 d . . . . .
C15 C 0.4551(8) 0.8500(8) 0.3620(13) 0.020(3) Uani 1 1 d . . . . .
H15 H 0.405545 0.836361 0.348554 0.024 Uiso 1 1 calc R U . . .
C16 C 0.500000 1.000000 0.636(2) 0.018(4) Uiso 1 2 d S . P . .
H16A H 0.487000 0.958070 0.687079 0.021 Uiso 1 1 d R U . . .
C17 C 0.5927(8) 1.0501(8) 0.5023(14) 0.018(3) Uani 1 1 d . . . . .
H17A H 0.630620 1.038501 0.442139 0.022 Uiso 1 1 calc R U . . .
H17B H 0.615648 1.080563 0.564739 0.022 Uiso 1 1 calc R U . . .
Cl50 Cl 0.2620(3) 0.6570(3) 0.1194(6) 0.0592(14) Uani 1 1 d . . . . .
C50 C 0.2802(12) 0.7472(12) 0.064(2) 0.047(5) Uani 1 1 d . . . . .
H50A H 0.330532 0.749127 0.031084 0.057 Uiso 1 1 calc R U . . .
H50B H 0.277210 0.782803 0.130232 0.057 Uiso 1 1 calc R U . . .
Cl51 Cl 0.2152(4) 0.7721(4) -0.0502(10) 0.086(3) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
I1 C1 2.111(14) . ?
C1 C6 1.38(2) . ?
C1 C2 1.39(2) . ?
N1 C4 1.456(18) . ?
N1 C8 1.46(2) . ?
N1 C7 1.466(19) . ?
I2 C10 2.084(16) . ?
C2 C3 1.38(2) . ?
C2 H2 0.9300 . ?
N2 C13 1.43(2) . ?
N2 C17 1.478(19) . ?
N2 C16 1.488(16) . ?
C3 C4 1.38(2) . ?
C3 C7 1.52(2) 2_665 ?
C4 C5 1.37(2) . ?
C5 C6 1.40(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 H8A 0.9700 . ?
C8 H8A 0.9700 2_665 ?
C10 C11 1.39(2) . ?
C10 C15 1.40(2) . ?
C11 C12 1.39(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.36(2) . ?
C12 H12 0.9300 . ?
C13 C14 1.42(2) . ?
C14 C15 1.37(2) . ?
C14 C17 1.54(2) 2_675 ?
C15 H15 0.9300 . ?
C16 H16A 0.9699 . ?
C16 H16A 0.9700 2_675 ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
Cl50 C50 1.76(2) . ?
C50 Cl51 1.77(3) . ?
C50 H50A 0.9700 . ?
C50 H50B 0.9700 . ?

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
C6 C1 C2 121.3(14) . . ?
C6 C1 I1 119.0(11) . . ?
C2 C1 I1 119.7(12) . . ?
C4 N1 C8 110.6(12) . . ?
C4 N1 C7 112.6(12) . . ?
C8 N1 C7 108.0(10) . . ?
C3 C2 C1 119.2(15) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C13 N2 C17 112.3(11) . . ?
C13 N2 C16 113.4(10) . . ?
C17 N2 C16 107.3(10) . . ?
C2 C3 C4 120.0(15) . . ?
C2 C3 C7 119.9(14) . 2_665 ?
C4 C3 C7 120.1(12) . 2_665 ?
C5 C4 C3 120.6(13) . . ?
C5 C4 N1 117.7(15) . . ?
C3 C4 N1 121.7(14) . . ?
C4 C5 C6 120.1(15) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 118.6(15) . . ?
C1 C6 H6 120.7 . . ?
C5 C6 H6 120.7 . . ?
N1 C7 C3 112.5(12) . 2_665 ?
N1 C7 H7A 109.1 . . ?
C3 C7 H7A 109.1 2_665 . ?
N1 C7 H7B 109.1 . . ?
C3 C7 H7B 109.1 2_665 . ?
H7A C7 H7B 107.8 . . ?
N1 C8 N1 111.2(18) 2_665 . ?
N1 C8 H8A 109.5 2_665 . ?
N1 C8 H8A 109.3 . . ?
N1 C8 H8A 109.3(6) 2_665 2_665 ?
N1 C8 H8A 109.5(6) . 2_665 ?
H8A C8 H8A 108.0 . 2_665 ?
C11 C10 C15 119.4(15) . . ?
C11 C10 I2 120.8(12) . . ?
C15 C10 I2 119.7(11) . . ?
C10 C11 C12 119.7(13) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C13 C12 C11 121.6(12) . . ?
C13 C12 H12 119.2 . . ?
C11 C12 H12 119.2 . . ?
C12 C13 C14 118.5(15) . . ?
C12 C13 N2 120.5(13) . . ?
C14 C13 N2 120.9(13) . . ?
C15 C14 C13 120.5(14) . . ?
C15 C14 C17 119.7(13) . 2_675 ?
C13 C14 C17 119.8(14) . 2_675 ?
C14 C15 C10 120.1(14) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?
N2 C16 N2 108.5(15) 2_675 . ?
N2 C16 H16A 110.0 2_675 . ?
N2 C16 H16A 110.0 . . ?
N2 C16 H16A 110.0(6) 2_675 2_675 ?
N2 C16 H16A 110.0(6) . 2_675 ?
H16A C16 H16A 108.3 . 2_675 ?
N2 C17 C14 110.9(12) . 2_675 ?
N2 C17 H17A 109.5 . . ?
C14 C17 H17A 109.5 2_675 . ?
N2 C17 H17B 109.5 . . ?
C14 C17 H17B 109.5 2_675 . ?
H17A C17 H17B 108.0 . . ?
Cl50 C50 Cl51 110.9(12) . . ?
Cl50 C50 H50A 109.5 . . ?
Cl51 C50 H50A 109.5 . . ?
Cl50 C50 H50B 109.5 . . ?
Cl51 C50 H50B 109.5 . . ?
H50A C50 H50B 108.0 . . ?

_refine_diff_density_max         1.840
_refine_diff_density_min         -2.291
_refine_diff_density_rms         0.320

####################################################################### 
# 
# 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_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1023122'
_audit_update_record             
;
2018-05-11 deposited with the CCDC.
2018-05-24 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         ?
_chemical_formula_sum            'C15 H12 I2 N2'
_chemical_formula_weight         474.07


_atom_type_scat_source           C

_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                   7.7955(5)
_cell_length_b                   36.484(7)
_cell_length_c                   10.5534(11)
_cell_angle_alpha                90
_cell_angle_beta                 105.088(7)
_cell_angle_gamma                90
_cell_volume                     2898.0(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    150
_cell_measurement_reflns_used    22692
_cell_measurement_theta_min      2.8901
_cell_measurement_theta_max      28.6319
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.29
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.173
_exptl_crystal_F_000             1776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    4.328
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Empirical
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.10 (release 13-04-2006 CrysAlis171 .NET)
(compiled Apr 13 2006,12:24:59)
?
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean 16.3990
_diffrn_reflns_number            56522
_diffrn_reflns_av_unetI/netI     0.0297
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -45
_diffrn_reflns_limit_k_max       45
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.608
_diffrn_reflns_theta_max         26.383
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5940
_reflns_number_gt                4901
_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       
;
CrysAlis CCD, Oxford Diffraction Ltd.,
Version 1.171.29.10 (release 13-04-2006 CrysAlis171 .NET)
(compiled Apr 13 2006,12:24:59)
;
_computing_cell_refinement       
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.10 (release 13-04-2006 CrysAlis171 .NET)
(compiled Apr 13 2006,12:24:59)
;
_computing_data_reduction        
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.29.10 (release 13-04-2006 CrysAlis171 .NET)
(compiled Apr 13 2006,12:24:59)
;
_computing_structure_solution    'SHELXTL Brüker'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0200P)²+15.5746P] 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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5940
_refine_ls_number_parameters     343
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.0744
_refine_ls_wR_factor_gt          0.0720
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_restrained_S_all      1.151
_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 0.44307(6) 0.00675(2) 0.23780(4) 0.03142(11) Uani 1 1 d . . . . .
C1 C 0.3415(7) 0.08679(15) 0.2164(5) 0.0191(11) Uani 1 1 d . . . . .
H1 H 0.348708 0.083422 0.130576 0.023 Uiso 1 1 calc R U . . .
I2 I 0.98569(5) 0.25861(2) 0.54069(4) 0.02205(9) Uani 1 1 d . . . . .
C2 C 0.3781(7) 0.05806(13) 0.3033(5) 0.0170(11) Uani 1 1 d . . . . .
C3 C 0.3696(7) 0.06228(14) 0.4317(5) 0.0192(11) Uani 1 1 d . . . . .
H3 H 0.396598 0.042796 0.490342 0.023 Uiso 1 1 calc R U . . .
I3 I -0.11463(6) 0.05153(2) 0.06913(4) 0.04302(13) Uani 1 1 d . . . . .
C4 C 0.3204(7) 0.09591(14) 0.4718(5) 0.0163(11) Uani 1 1 d . . . . .
H4 H 0.314060 0.099040 0.557953 0.020 Uiso 1 1 calc R U . . .
C4A C 0.2804(6) 0.12500(14) 0.3841(5) 0.0156(11) Uani 1 1 d . . . . .
I4 I 0.61866(5) 0.16953(2) 0.91186(4) 0.02658(10) Uani 1 1 d . . . . .
N5 N 0.2216(6) 0.15895(11) 0.4276(4) 0.0161(9) Uani 1 1 d . . . . .
C6 C 0.3675(7) 0.17966(14) 0.5145(5) 0.0185(11) Uani 1 1 d . . . . .
H6A H 0.442428 0.162949 0.576322 0.022 Uiso 1 1 calc R U . . .
H6B H 0.318478 0.197350 0.564107 0.022 Uiso 1 1 calc R U . . .
C6A C 0.4790(7) 0.19951(13) 0.4384(5) 0.0154(11) Uani 1 1 d . . . . .
C7 C 0.6409(7) 0.21508(13) 0.5046(5) 0.0152(10) Uani 1 1 d . . . . .
H7 H 0.675719 0.214621 0.595831 0.018 Uiso 1 1 calc R U . . .
C8 C 0.7497(7) 0.23110(13) 0.4367(5) 0.0167(11) Uani 1 1 d . . . . .
C9 C 0.7017(7) 0.23125(13) 0.3005(5) 0.0187(11) Uani 1 1 d . . . . .
H9 H 0.778134 0.240963 0.254644 0.022 Uiso 1 1 calc R U . . .
C10 C 0.5393(7) 0.21684(14) 0.2335(5) 0.0187(11) Uani 1 1 d . . . . .
H10 H 0.505405 0.217550 0.142256 0.022 Uiso 1 1 calc R U . . .
C10A C 0.4264(7) 0.20131(13) 0.3010(5) 0.0162(11) Uani 1 1 d . . . . .
N11 N 0.2550(6) 0.18800(11) 0.2291(4) 0.0164(9) Uani 1 1 d . . . . .
C12 C 0.2641(7) 0.15271(14) 0.1615(5) 0.0193(11) Uani 1 1 d . . . . .
H12A H 0.360133 0.153749 0.118804 0.023 Uiso 1 1 calc R U . . .
H12B H 0.154092 0.149019 0.094224 0.023 Uiso 1 1 calc R U . . .
C12A C 0.2940(7) 0.12069(14) 0.2552(5) 0.0170(11) Uani 1 1 d . . . . .
C13 C 0.1395(7) 0.18235(15) 0.3169(5) 0.0194(11) Uani 1 1 d . . . . .
H13A H 0.111788 0.205909 0.349372 0.023 Uiso 1 1 calc R U . . .
H13B H 0.028871 0.171315 0.267957 0.023 Uiso 1 1 calc R U . . .
C21 C -0.0984(7) 0.05423(14) 0.3595(6) 0.0247(13) Uani 1 1 d . . . . .
H21 H -0.054663 0.030582 0.357656 0.030 Uiso 1 1 calc R U . . .
C22 C -0.1428(7) 0.07465(15) 0.2453(5) 0.0212(12) Uani 1 1 d . . . . .
C23 C -0.2071(7) 0.11009(15) 0.2465(6) 0.0238(12) Uani 1 1 d . . . . .
H23 H -0.235707 0.123983 0.170040 0.029 Uiso 1 1 calc R U . . .
C24 C -0.2284(7) 0.12456(14) 0.3629(5) 0.0205(12) Uani 1 1 d . . . . .
H24 H -0.271001 0.148339 0.363853 0.025 Uiso 1 1 calc R U . . .
C24A C -0.1870(7) 0.10413(14) 0.4786(5) 0.0188(11) Uani 1 1 d . . . . .
N25 N -0.2184(6) 0.11955(11) 0.5945(4) 0.0178(9) Uani 1 1 d . . . . .
C26 C -0.0835(7) 0.14682(14) 0.6558(5) 0.0180(11) Uani 1 1 d . . . . .
H26A H -0.131145 0.162599 0.712332 0.022 Uiso 1 1 calc R U . . .
H26B H -0.056727 0.161974 0.587887 0.022 Uiso 1 1 calc R U . . .
C26A C 0.0861(7) 0.12935(14) 0.7356(5) 0.0175(11) Uani 1 1 d . . . . .
C27 C 0.2365(7) 0.15115(14) 0.7822(5) 0.0175(11) Uani 1 1 d . . . . .
H27 H 0.229553 0.176404 0.769930 0.021 Uiso 1 1 calc R U . . .
C28 C 0.3954(7) 0.13503(14) 0.8464(5) 0.0195(11) Uani 1 1 d . . . . .
C29 C 0.4085(7) 0.09732(15) 0.8681(5) 0.0201(12) Uani 1 1 d . . . . .
H29 H 0.516553 0.086634 0.910527 0.024 Uiso 1 1 calc R U . . .
C30 C 0.2587(7) 0.07634(15) 0.8256(5) 0.0205(12) Uani 1 1 d . . . . .
H30 H 0.265292 0.051216 0.840955 0.025 Uiso 1 1 calc R U . . .
C30A C 0.0964(7) 0.09188(14) 0.7598(5) 0.0180(11) Uani 1 1 d . . . . .
N31 N -0.0576(6) 0.06880(12) 0.7205(4) 0.0206(10) Uani 1 1 d . . . . .
C32 C -0.0621(7) 0.04662(14) 0.6036(6) 0.0236(12) Uani 1 1 d . . . . .
H32A H -0.144081 0.026396 0.599656 0.028 Uiso 1 1 calc R U . . .
H32B H 0.055019 0.036374 0.611222 0.028 Uiso 1 1 calc R U . . .
C32A C -0.1182(7) 0.06850(14) 0.4777(5) 0.0188(11) Uani 1 1 d . . . . .
C33 C -0.2189(7) 0.09098(15) 0.6923(6) 0.0225(12) Uani 1 1 d . . . . .
H33A H -0.230144 0.102388 0.772795 0.027 Uiso 1 1 calc R U . . .
H33B H -0.321209 0.075208 0.660219 0.027 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 C2 2.103(5) . ?
C1 C2 1.373(7) . ?
C1 C12A 1.384(7) . ?
C1 H1 0.9300 . ?
I2 C8 2.132(5) . ?
C2 C3 1.383(7) . ?
C3 C4 1.384(7) . ?
C3 H3 0.9300 . ?
I3 C22 2.104(5) . ?
C4 C4A 1.390(7) . ?
C4 H4 0.9300 . ?
C4A C12A 1.401(7) . ?
C4A N5 1.437(6) . ?
I4 C28 2.113(5) . ?
N5 C13 1.454(7) . ?
N5 C6 1.470(7) . ?
C6 C6A 1.512(7) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6A C7 1.394(7) . ?
C6A C10A 1.402(7) . ?
C7 C8 1.375(7) . ?
C7 H7 0.9300 . ?
C8 C9 1.388(7) . ?
C9 C10 1.383(8) . ?
C9 H9 0.9300 . ?
C10 C10A 1.390(7) . ?
C10 H10 0.9300 . ?
C10A N11 1.438(7) . ?
N11 C13 1.466(6) . ?
N11 C12 1.482(6) . ?
C12 C12A 1.509(7) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C21 C22 1.382(8) . ?
C21 C32A 1.396(8) . ?
C21 H21 0.9300 . ?
C22 C23 1.388(8) . ?
C23 C24 1.385(8) . ?
C23 H23 0.9300 . ?
C24 C24A 1.395(8) . ?
C24 H24 0.9300 . ?
C24A C32A 1.407(7) . ?
C24A N25 1.425(7) . ?
N25 C33 1.468(7) . ?
N25 C26 1.470(7) . ?
C26 C26A 1.511(7) . ?
C26 H26A 0.9700 . ?
C26 H26B 0.9700 . ?
C26A C30A 1.389(7) . ?
C26A C27 1.396(7) . ?
C27 C28 1.379(8) . ?
C27 H27 0.9300 . ?
C28 C29 1.394(7) . ?
C29 C30 1.371(8) . ?
C29 H29 0.9300 . ?
C30 C30A 1.395(7) . ?
C30 H30 0.9300 . ?
C30A N31 1.436(7) . ?
N31 C33 1.460(7) . ?
N31 C32 1.468(7) . ?
C32 C32A 1.514(7) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C12A 120.6(5) . . ?
C2 C1 H1 119.7 . . ?
C12A C1 H1 119.7 . . ?
C1 C2 C3 121.0(5) . . ?
C1 C2 I1 119.1(4) . . ?
C3 C2 I1 119.9(4) . . ?
C2 C3 C4 119.1(5) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C4 C4A 120.3(5) . . ?
C3 C4 H4 119.8 . . ?
C4A C4 H4 119.8 . . ?
C4 C4A C12A 120.0(5) . . ?
C4 C4A N5 118.7(4) . . ?
C12A C4A N5 121.2(4) . . ?
C4A N5 C13 111.1(4) . . ?
C4A N5 C6 112.5(4) . . ?
C13 N5 C6 107.8(4) . . ?
N5 C6 C6A 111.9(4) . . ?
N5 C6 H6A 109.2 . . ?
C6A C6 H6A 109.2 . . ?
N5 C6 H6B 109.2 . . ?
C6A C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
C7 C6A C10A 118.8(5) . . ?
C7 C6A C6 120.0(4) . . ?
C10A C6A C6 121.2(5) . . ?
C8 C7 C6A 120.8(5) . . ?
C8 C7 H7 119.6 . . ?
C6A C7 H7 119.6 . . ?
C7 C8 C9 120.3(5) . . ?
C7 C8 I2 119.9(4) . . ?
C9 C8 I2 119.7(4) . . ?
C10 C9 C8 119.5(5) . . ?
C10 C9 H9 120.3 . . ?
C8 C9 H9 120.3 . . ?
C9 C10 C10A 120.7(5) . . ?
C9 C10 H10 119.6 . . ?
C10A C10 H10 119.6 . . ?
C10 C10A C6A 119.7(5) . . ?
C10 C10A N11 119.5(5) . . ?
C6A C10A N11 120.8(5) . . ?
C10A N11 C13 110.7(4) . . ?
C10A N11 C12 113.1(4) . . ?
C13 N11 C12 107.2(4) . . ?
N11 C12 C12A 112.1(4) . . ?
N11 C12 H12A 109.2 . . ?
C12A C12 H12A 109.2 . . ?
N11 C12 H12B 109.2 . . ?
C12A C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C1 C12A C4A 118.8(5) . . ?
C1 C12A C12 120.4(5) . . ?
C4A C12A C12 120.8(5) . . ?
N5 C13 N11 112.1(4) . . ?
N5 C13 H13A 109.2 . . ?
N11 C13 H13A 109.2 . . ?
N5 C13 H13B 109.2 . . ?
N11 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C22 C21 C32A 121.2(5) . . ?
C22 C21 H21 119.4 . . ?
C32A C21 H21 119.4 . . ?
C21 C22 C23 120.2(5) . . ?
C21 C22 I3 119.7(4) . . ?
C23 C22 I3 120.2(4) . . ?
C24 C23 C22 119.4(5) . . ?
C24 C23 H23 120.3 . . ?
C22 C23 H23 120.3 . . ?
C23 C24 C24A 121.2(5) . . ?
C23 C24 H24 119.4 . . ?
C24A C24 H24 119.4 . . ?
C24 C24A C32A 119.3(5) . . ?
C24 C24A N25 119.2(5) . . ?
C32A C24A N25 121.4(5) . . ?
C24A N25 C33 110.9(4) . . ?
C24A N25 C26 112.5(4) . . ?
C33 N25 C26 107.7(4) . . ?
N25 C26 C26A 112.5(4) . . ?
N25 C26 H26A 109.1 . . ?
C26A C26 H26A 109.1 . . ?
N25 C26 H26B 109.1 . . ?
C26A C26 H26B 109.1 . . ?
H26A C26 H26B 107.8 . . ?
C30A C26A C27 119.5(5) . . ?
C30A C26A C26 121.2(5) . . ?
C27 C26A C26 119.2(5) . . ?
C28 C27 C26A 119.6(5) . . ?
C28 C27 H27 120.2 . . ?
C26A C27 H27 120.2 . . ?
C27 C28 C29 121.3(5) . . ?
C27 C28 I4 117.7(4) . . ?
C29 C28 I4 121.0(4) . . ?
C30 C29 C28 118.5(5) . . ?
C30 C29 H29 120.8 . . ?
C28 C29 H29 120.8 . . ?
C29 C30 C30A 121.4(5) . . ?
C29 C30 H30 119.3 . . ?
C30A C30 H30 119.3 . . ?
C26A C30A C30 119.5(5) . . ?
C26A C30A N31 121.3(5) . . ?
C30 C30A N31 119.1(5) . . ?
C30A N31 C33 110.2(4) . . ?
C30A N31 C32 113.6(4) . . ?
C33 N31 C32 107.7(4) . . ?
N31 C32 C32A 112.6(4) . . ?
N31 C32 H32A 109.1 . . ?
C32A C32 H32A 109.1 . . ?
N31 C32 H32B 109.1 . . ?
C32A C32 H32B 109.1 . . ?
H32A C32 H32B 107.8 . . ?
C21 C32A C24A 118.8(5) . . ?
C21 C32A C32 120.9(5) . . ?
C24A C32A C32 120.3(5) . . ?
N31 C33 N25 112.2(4) . . ?
N31 C33 H33A 109.2 . . ?
N25 C33 H33A 109.2 . . ?
N31 C33 H33B 109.2 . . ?
N25 C33 H33B 109.2 . . ?
H33A C33 H33B 107.9 . . ?

_refine_diff_density_max         1.102
_refine_diff_density_min         -1.036
_refine_diff_density_rms         0.139

